(19)
(11)EP 3 389 105 A1

(12)EUROPEAN PATENT APPLICATION
published in accordance with Art. 153(4) EPC

(43)Date of publication:
17.10.2018 Bulletin 2018/42

(21)Application number: 16872911.9

(22)Date of filing:  02.12.2016
(51)Int. Cl.: 
H01L 51/50  (2006.01)
C07F 15/00  (2006.01)
C09K 11/06  (2006.01)
(86)International application number:
PCT/JP2016/085890
(87)International publication number:
WO 2017/099013 (15.06.2017 Gazette  2017/24)
(84)Designated Contracting States:
AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR
Designated Extension States:
BA ME
Designated Validation States:
MA MD

(30)Priority: 07.12.2015 JP 2015238657

(71)Applicant: Sumitomo Chemical Company, Limited
Tokyo 104-8260 (JP)

(72)Inventors:
  • SAITO Takakazu
    Tsukuba-shi Ibaraki 300-3294 (JP)
  • SASADA Toshiaki
    Tsukuba-shi Ibaraki 300-3294 (JP)

(74)Representative: J A Kemp 
14 South Square Gray's Inn
London WC1R 5JJ
London WC1R 5JJ (GB)

  


(54)COMPOSITION AND LIGHT-EMITTING ELEMENT IN WHICH SAME IS USED


(57) A composition, comprising: a phosphorescent compound represented by formula (1); and a phosphorescent compound represented by formula (2):

(wherein M1 represents an iridium atom or the like, n1 denotes an integer of 1 or more, n2 denotes an integer of 0 or more, n1 + n2 is 2 or 3, ring R1A represents a triazole ring constituted of a nitrogen atom, E1, E11A, E12A, and a carbon atom, ring R2 represents an aromatic hydrocarbon ring or the like, E1, E2, E11A, and E12A represent a nitrogen atom or the like, R11A and R12A represent an aryl group or the like, R13A represents an aryl group or the like, A1-G1-A2 represents an anionic bidentate ligand, A1 and A2 represent a nitrogen atom or the like, and G1 represents a single bond or the like)

(wherein M2 represents an iridium atom or the like, n3 denotes an integer of 1 or more, n4 denotes an integer of 0 or more, n3 + n4 is 2 or 3, EL represents a hydrogen atom or a nitrogen atom, ring L1 represents a 6-membered aromatic heterocyclic ring or the like, ring L2 represents an aromatic hydrocarbon ring or the like, at least one ring selected from the group consisting of ring L1 and ring L2 has a group represented by formula (1-T), A3-G2-A4 represents an anionic bidentate ligand, A3 and A4 represent a nitrogen atom or the like, and G2 represents a single bond or the like), and

        -R1T     (1-T)

(wherein R1T represents an alkyl group or the like).


Description

Technical Field



[0001] The present invention relates to a composition and a light-emitting device using the same.

Background Art



[0002] An organic electroluminescent device (hereinafter also referred to as "light-emitting device") shows a high luminous efficiency and a low drive voltage, and hence can be suitably used for display and lighting applications. Research and development into such devices is being actively carried out.

[0003] As a material to be used for a light-emitting layer of a light-emitting device, for example, a composition comprising a phosphorescent compound (A), a phosphorescent compound (B), and a phosphorescent compound (C) represented by the following formulas has been proposed (Patent Literature 1). It is noted that the phenyl-pyridine ligand of the phosphorescent compound (B) and the benzothienyl-pyridine ligand of the phosphorescent compound (C) are ligands having no substituent.




Citation List


Patent Literature



[0004] [Patent Literature 1] International Publication No. 2014/156922

Summary of Invention


Technical Problem



[0005] However, a light-emitting device fabricated using the composition described in Patent Literature 1 does not always show a sufficient external quantum efficiency.

[0006] Therefore, it is an object of the present invention to provide a composition useful for the fabrication of a light-emitting device which shows an excellent external quantum efficiency. Further, it is another object of the present invention to provide a light-emitting device comprising this composition.

Solution to Problem



[0007] The present invention provides the following [1] to [15].
  1. [1] A composition, comprising:

    a phosphorescent compound represented by formula (1); and

    a phosphorescent compound represented by formula (2):

    (wherein,

    M1 represents a rhodium atom, a palladium atom, an iridium atom or a platinum atom,

    n1 denotes an integer of 1 or more, n2 denotes an integer of 0 or more, and n1 + n2 is 2 or 3,

    when M1 is a rhodium atom or an iridium atom, n1 + n2 is 3, and when M1 is a palladium atom or a platinum atom, n1 + n2 is 2,

    ring R1A represents a triazole ring or a diazole ring constituted of a nitrogen atom, E1, E11A, E12A, and a carbon atom,

    ring R2 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings each may have a substituent; when there are a plurality of such substituents, those substituents may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded; and when there are a plurality of rings R2, those rings may be the same or different,

    E1, E2, E11A, and E12A each independently represent a nitrogen atom or a carbon atom; when there are a plurality of E1, E2, E11A and E12A, they may be the same or different at each occurrence; provided that at least one of E1 and E2 is a carbon atom,

    R11A and R12A each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom, and these groups each may have a substituent; when there are a plurality of R11A and R12A, they may be the same or different at each occurrence,

    R11A and R12A may be bonded to each other to form a ring together with the atoms to which they are bonded; and R11A and an optional substituent of the ring R2 may be bonded to each other to form a ring together with the atoms to which they are bonded,

    when E11A is a nitrogen atom, R11A may be present or absent, and when E12A is a nitrogen atom, R12A may be present or absent,

    R13A represents an aryl group, a monovalent heterocyclic group, or a substituted amino group, and these groups each may have a substituent; when there are a plurality of R13A, they may be the same or different; and R12A and R13A may be bonded to each other to form a ring together with the atoms to which they are bonded, and

    A1-G1-A2 represents an anionic bidentate ligand, A1 and A2 each independently represent a carbon atom, an oxygen atom or a nitrogen atom, and these atoms may be atoms constituting a ring; G1 represents a single bond or an atomic group constituting the bidentate ligand together with A1 and A2; and when there are a plurality of A1-G1-A2, they may be the same or different).

    (wherein,

    M2 represents a rhodium atom, a palladium atom, an iridium atom or a platinum atom,

    n3 denotes an integer of 1 or more, n4 denotes an integer of 0 or more, and n3 + n4 is 2 or 3; when M2 is a rhodium atom or an iridium atom, n3 + n4 is 3; and when M2 is a palladium atom or a platinum atom, n3 + n4 is 2,

    EL represents a carbon atom or a nitrogen atom,

    ring L1 represents a 6-membered aromatic heterocyclic ring, which may have a substituent; when there are a plurality of such substituents, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded; and when there are a plurality of rings L1, they may be the same or different,

    ring L2 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings each may have a substituent; when there are a plurality of such substituents, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded; and when there are a plurality of rings L2, they may be the same or different,

    an optional substituent of the ring L1 and an optional substituent of the ring L2 may combine with each other to form a ring together with the atoms to which they are bonded,

    provided that at least one ring selected from the group consisting of ring L1 and ring L2 has at least one group represented by formula (1-T); and when there are a plurality of groups represented by formula (1-T), they may be the same or different,

    A3-G2-A4 represents an anionic bidentate ligand, A3 and A4 each independently represent a carbon atom, an oxygen atom or a nitrogen atom, and these atoms may be atoms constituting a ring; G2 represents a single bond or an atomic group constituting the bidentate ligand together with A3 and A4; and when there are a plurality of A3-G2-A4, they may be the same or different).
    [Chemical Formula 4]

            -R1T     (1-T)

    (wherein,
    R1T represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryloxy group, a halogen atom, an aryl group, a monovalent heterocyclic group, or a substituted amino group, and these groups each may have a substituent).

  2. [2] The composition according to [1], wherein the phosphorescent compound represented by formula (2) is a phosphorescent compound represented by formula (2-B):



    (wherein,

    M2, n3, n4, and A3-G2-A4 have the same meaning as described above,

    E11B, E12B, E13B, E14B, E21B, E22B, E23B, and E24B each independently represent a nitrogen atom or a carbon atom; when there are a plurality of E11B, E12B, E13B, E14B, E21B, E22B, E23B, and E24B, they may be the same or different at each occurrence; when E11B is a nitrogen atom, R11B is absent; when E12B is a nitrogen atom, R12B is absent, when E13B is a nitrogen atom, R13B is absent; when E14B is a nitrogen atom, R14B is absent; when E21B is a nitrogen atom, R21B is absent; when E22B is a nitrogen atom, R22B is absent; when E23B is a nitrogen atom, R23B is absent; and when E24B is a nitrogen atom, R24B is absent,

    R11B, R12B, R13B, R14B, R21B, R22B, R23B, and R24B each independently represent a hydrogen atom or a group represented by formula (1-T); when there are a plurality of R11B, R12B, R13B, R14B, R21B, R22B, R23B, and R24B, they may be the same or different at each occurrence; and R11B and R12B, R12B and R13B, R13B and R14B, R11B and R21B, R21B and R22B, R22B and R23B, and R23B and R24B each may be bonded to each other to form a ring together with the atoms to which they are bonded; provided that at least one selected from the group consisting of R11B, R12B, R13B, R14B, R21B, R22B, R23B, and R24B is a group represented by formula (1-T),

    ring L1B represents a pyridine ring or a pyrimidine ring constituted of a nitrogen atom, a carbon atom, E11B, E12B, E13B, and E14B, and

    ring L2B represents a benzene ring, a pyridine ring, or a pyrimidine ring constituted of two carbon atoms, E21B, E22B, E23B, and E24B).

  3. [3] The composition according to [2], wherein the phosphorescent compound represented by formula (2-B) is a phosphorescent compound represented by formula (2-B1), a phosphorescent compound represented by formula (2-B2), a phosphorescent compound represented by formula (2-B3), a phosphorescent compound represented by formula (2-B4), or a phosphorescent compound represented by formula (2-B5):



    (wherein,

    M2, n3, n4, R11B, R12B, R13B, R14B, R21B, R22B, R23B, R24B, and A3-G2-A4 have the same meanings as described above,

    n31 and n32 each independently denote an integer of 1 or more, and n31 + n32 is 2 or 3; when M2 is a rhodium atom or an iridium atom, n31 + n32 is 3; and when M2 is a palladium atom or a platinum atom, n31 + n32 is 2, and

    R15B, R16B, R17B, and R18B each independently represent a hydrogen atom or a group represented by formula (1-T); when there are a plurality of R15B, R16B, R17B, and R18B, they may be the same or different at each occurrence; R15B and R16B, R16B and R17B, and R17B and R18B each may be bonded to each other to form a ring together with the atoms to which they are bonded,

    provided that, in formulas (2-B1) and (2-B3), at least one selected from the group consisting of R11B, R12B, R13B, R14B, R21B, R22B, R23B, and R24B is a group represented by formula (1-T); in formula (2-B2), at least one selected from the group consisting of R13B, R14B, R21B, R22B, R23B, and R24B is a group represented by formula (1-T); in formula (2-B4), at least one selected from the group consisting of R11B, R14B, R21B, R22B, R23B, and R24B is a group represented by formula (1-T); and in formula (2-B5), at least one selected from the group consisting of R11B, R12B, R21B, R22B, R23B, and R24B is a group represented by formula (1-T)).

  4. [4] The composition according to any one of [1] to [3], wherein R1T is an alkyl group, a cycloalkyl group, a group represented by formula (D-A), a group represented by formula (D-B), or a group represented by formula (D-C):

    (wherein,

    mDA1, mDA2, and mDA3 each independently denote an integer of 0 or more,

    GDA represents a nitrogen atom, an aromatic hydrocarbon group, or a heterocyclic group, and these groups each may have a substituent,

    ArDA1, ArDA2, and ArDA3 each independently represent an arylene group or a divalent heterocyclic group, and these groups each may have a substituent; and when there are a plurality of ArDA1, ArDA2, and ArDA3, they may be the same or different at each occurrence, and

    TDA represents an aryl group or a monovalent heterocyclic group, and these groups each may have a substituent; and the plurality of TDA may be the same or different),

    (wherein,

    mDA1, mDA2, mDA3, mDA4, mDA5, mDA6, and mDA7 each independently denote an integer of 0 or more,

    GDA represents a nitrogen atom, an aromatic hydrocarbon group, or a heterocyclic group, and these groups each may have a substituent; and the plurality of GDA may be the same or different,

    ArDA1, ArDA2, ArDA3, ArDA4, ArDA5, ArDA6, and ArDA7 each independently represent an arylene group or a divalent heterocyclic group, and these groups each may have a substituent; and when there are a plurality of ArDA1, ArDA2, ArDA3, ArDA4, ArDA5, ArDA6, and ArDA7, they may be the same or different at each occurrence, and

    TDA represents an aryl group or a monovalent heterocyclic group, and these groups each may have a substituent; and the plurality of TDA may be the same or different), and

    (wherein,

    mDA1 denotes an integer of 0 or more,

    ArDA1 represents an arylene group or a divalent heterocyclic group, and these groups each may have a substituent; and when there are a plurality of ArDA1, they may be the same or different, and

    TDA represents an aryl group or a monovalent heterocyclic group, and these groups each may have a substituent).

  5. [5] The composition according to [4],
    wherein R1T is a group represented by formula (D-A), and
    wherein the group represented by formula (D-A) is a group represented by formula (D-A1), a group represented by formula (D-A2), a group represented by formula (D-A3), or a group represented by formula (D-A4):



    (wherein,
    Rp1, Rp2, Rp3, and Rp4 each independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or a halogen atom; and when there are a plurality of Rp1, Rp2, and Rp4, they may be the same or different at each occurrence, and
    np1 denotes an integer of 0 to 5, np2 denotes an integer of 0 to 3, np3 represents 0 or 1, and np4 denotes an integer of 0 to 4; and the plurality of np1 may be the same or different).
  6. [6] The composition according to [4],
    wherein R1T is a group represented by formula (D-B), and
    wherein the group represented by formula (D-B) is a group represented by formula (D-B1), a group represented by formula (D-B2), or a group represented by formula (D-B3):



    (wherein,

    Rp1, Rp2, and Rp3 each independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or a halogen atom; and when there are a plurality of Rp1 and Rp2, they may be the same or different at each occurrence, and

    np1 denotes an integer of 0 to 5, np2 denotes an integer of 0 to 3, and np3 represents 0 or 1; and when there are a plurality of np1 and np2, they may be the same or different at each occurrence).

  7. [7] The composition according to [4],
    wherein R1T is a group represented by formula (D-C), and
    wherein the group represented by formula (D-C) is a group represented by formula (D-C1), a group represented by formula (D-C2), a group represented by formula (D-C3), or a group represented by formula (D-C4):

    (wherein,

    Rp4, Rp5, and Rp6 each independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or a halogen atom; and when there are a plurality of Rp4, Rp5, and Rp6, they may be the same or different at each occurrence, and

    np4 denotes an integer of 0 to 4, np5 denotes an integer of 0 to 5, and np6 denotes an integer of 0 to 5).

  8. [8] The composition according to any one of [1] to [7], wherein the phosphorescent compound represented by formula (1) is a phosphorescent compound represented by formula (1-A):

    (wherein,

    M1, n1, n2, ring R1A, E1, E11A, E12A, R11A, R12A, R13A, and A1-G1-A2 have the same meanings as described above,

    ring R2A represents a benzene ring, a pyridine ring, or a pyrimidine ring constituted of two carbon atoms, E21A, E22A, E23A, and E24A,

    E21A, E22A, E23A, and E24A each independently represent a nitrogen atom or a carbon atom; when there are a plurality of E21A, E22A, E23A, and E24A, they may be the same or different at each occurrence; when E21A is a nitrogen atom, R21A is absent; when E22A is a nitrogen atom, R22A is absent; when E23A is a nitrogen atom, R23A is absent; and when E24A is a nitrogen atom, R24A is absent, and

    R21A, R22A, R23A, and R24A each represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom, and these groups each may have a substituent; when there are a plurality of R21A, R22A, R23A, and R24A, they may be the same or different at each occurrence; R21A and R22A may be bonded to each other to form a ring together with the atoms to which they are bonded; R22A and R23A may be bonded to each other to form a ring together with the atoms to which they are bonded; R23A and R24A may be bonded to each other to form a ring together with the atoms to which they are bonded; and R11A and R21A may be bonded to each other to form a ring together with the atoms to which they are bonded).

  9. [9] The composition according to [8], wherein the phosphorescent compound represented by formula (1-A) is a phosphorescent compound represented by formula (1-A1), a phosphorescent compound represented by formula (1-A2), a phosphorescent compound represented by formula (1-A3), or a phosphorescent compound represented by formula (1-A4):



    (wherein M1, n1, n2, R11A, R12A, R13A, R21A, R22A, R23A, R24A, and A1-G1-A2 have the same meanings as described above).
  10. [10] The composition according to any of [1] to [9], wherein R13A is an aryl group which may have a substituent.
  11. [11] The composition according to any one of [1] to [10], wherein the composition comprises two or more phosphorescent compounds represented by formula (2).
  12. [12] The composition according to any one of [1] to [11],
    wherein the maximum peak wavelength of the emission spectrum of the phosphorescent compound represented by formula (1) is 380 nm or more and less than 495 nm, and
    wherein the maximum peak wavelength of the emission spectrum of the phosphorescent compound represented by formula (2) is 495 nm or more and less than 750 nm.
  13. [13] The composition according to any one of [1] to [12], further comprising a compound represented by formula (H-1):

    (wherein,

    ArH1 and ArH2 each independently represent an aryl group or a monovalent heterocyclic group, and these groups each may have a substituent,

    nH1 and nH2 each independently denote 0 or 1; when there are a plurality of nH1, they may be the same or different; and the plurality of nH2 may be the same or different;

    nH3 denotes an integer of 0 or more,

    LH1 represents an arylene group, a divalent heterocyclic group, or a group represented by -[C(RH11)2]nH11-, and these groups each may have a substituent; when there are a plurality of LH1, they may be the same or different,

    nH11 denotes an integer of 1 or more and 10 or less; RH11 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups each may have a substituent; and the plurality of RH11 may be the same or different and may be bonded to each other to form a ring together with the carbon atom to which they are bonded,

    LH2 represents a group represented by -N(-LH21-RH21)-; when there are a plurality of LH2, they may be the same or different, and

    LH21 represents a single bond, an arylene group, or a divalent heterocyclic group, and these groups each may have a substituent; RH21 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups each may have a substituent).

  14. [14] The composition according to any one of [1] to [13], further comprising at least one material selected from the group consisting of a hole transporting material, a hole injecting material, an electron transporting material, an electron injecting material, a light emitting material, an antioxidant, and a solvent.
  15. [15] A light-emitting device, comprising:

    an anode;

    a cathode; and

    a layer provided between the anode and the cathode, and comprising the composition according to any one of [1] to [14].


Advantageous Effects of Invention



[0008] According to the present invention, a composition useful for the fabrication of a light-emitting device which shows an excellent external quantum efficiency can be provided. Further, according to the present invention, a light-emitting device comprising this composition can be provided.

Description of Embodiments



[0009] Preferable embodiments of the present invention will now be described in detail.

<Description of Common Terms>



[0010] Unless otherwise stated, terms commonly used in the present specification have the following meanings.

[0011] Me represents a methyl group, Et represents an ethyl group, Bu represents a butyl group, i-Pr represents an isopropyl group, and t-Bu represents a tert-butyl group.

[0012] The hydrogen atom may be a heavy hydrogen atom or a light hydrogen atom.

[0013] In the formula representing a phosphorescent compound, a solid line representing a bond to the central metal represents a covalent bond or a coordinate bond.

[0014] The term "polymer compound" means a polymer having molecular weight distribution and having a polystyrene-equivalent number-average molecular weight of 1 × 103 to 1 × 108.

[0015] The polymer compound may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, or may even be some other form.

[0016] If a polymerization active group remains intact at the terminal group of the polymer compound, light-emitting properties may deteriorate if such a polymer compound is used to fabricate the light-emitting device, and therefore, it is preferable that the terminal group be a stable group. This terminal group is preferably a group covalently bonded to the main chain, and examples thereof include groups bonding to an aryl group or a monovalent heterocyclic group via a carbon-carbon bond.

[0017] The term "low molecular weight compound" means a compound that does not have a molecular weight distribution and that has a molecular weight of 1 × 104 or less.

[0018] The term "constitutional unit" means a unit occurring one or more times in a polymer compound.

[0019] The "alkyl group" may be either linear or branched. The linear alkyl group usually has 1 to 50 carbon atoms, preferably 3 to 30 carbon atoms, and more preferably 4 to 20 carbon atoms, not including the carbon atoms of the substituent. The branched alkyl group usually has 3 to 50 carbon atoms, preferably 3 to 30 carbon atoms, and more preferably 4 to 20 carbon atoms, not including the carbon atoms of the substituent.

[0020] The alkyl group may have a substituent, and examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a 2-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, an isoamyl group, 2-ethylbutyl group, a hexyl group, a heptyl group, an octyl group, a 2-ethylhexyl group, a 3-propylheptyl group, a decyl group, a 3,7-dimethyloctyl group, a 2-ethyloctyl group, a 2-hexyldecyl group, and a dodecyl group, and groups obtained by substituting a hydrogen atom of these groups with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, and the like; and examples thereof include a trifluoromethyl group, a pentafluoroethyl group, a perfluorobutyl group, a perfluorohexyl group, a perfluorooctyl group, a 3-phenylpropyl group, a 3-(4-methylphenyl)propyl group, a 3-(3,5-di-hexylphenyl)propyl group, and a 6-ethyloxyhexyl group.

[0021] The "cycloalkyl group" usually has 3 to 50 carbon atoms, preferably 3 to 30 carbon atoms, and more preferably 4 to 20 carbon atoms, not including the carbon atoms of the substituent.

[0022] The cycloalkyl group may have a substituent, and examples thereof include a cyclohexyl group, a cyclohexylmethyl group, and a cyclohexylethyl group.

[0023] The term "aryl group" means the atomic group remaining after removing from an aromatic hydrocarbon one hydrogen atom that is directly bonded to a carbon atom constituting the ring. The aryl group usually has 6 to 60 carbon atoms, preferably 6 to 20 carbon atoms, and more preferably 6 to 10 carbon atoms, not including the carbon atoms of the substituent.

[0024] The aryl group may have a substituent, and examples thereof include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthracenyl group, a 2-anthracenyl group, a 9-anthracenyl group, a 1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenyl group, a 2-fluorenyl group, a 3-fluorenyl group, a 4-fluorenyl group, a 2-phenylphenyl group, a 3-phenylphenyl group, and a 4-phenylphenyl group, and groups obtained by substituting a hydrogen atom of these groups with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, and the like.

[0025] The "alkoxy group" may be any of linear and branched. The linear alkoxy group usually has 1 to 40 carbon atoms, and preferably 4 to 10 carbon atoms, not including the carbon atoms of the substituent. The branched alkoxy group usually has 3 to 40 carbon atoms, and preferably 4 to 10 carbon atoms, not including the carbon atoms of the substituent.

[0026] The alkoxy group may have a substituent, and examples thereof include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group, an isobutyloxy group, a tert-butyloxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a 2-ethylhexyloxy group, a nonyloxy group, a decyloxy group, a 3,7-dimethyloctyloxy group, and a lauryloxy group, and groups obtained by substituting a hydrogen atom of these groups with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, and the like.

[0027] The "cycloalkoxy group" usually has 3 to 40 carbon atoms, and preferably 4 to 10 carbon atoms, not including the carbon atoms of the substituent.

[0028] The cycloalkoxy group may have a substituent, and examples thereof include a cyclohexyloxy group.

[0029] The "aryloxy group" usually has 6 to 60 carbon atoms, and preferably 6 to 48, not including the carbon atoms of the substituent.

[0030] The aryloxy group may have a substituent, and examples thereof include a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 1-anthracenyloxy group, a 9-anthracenyloxy group, and a 1-pyrenyloxy group, and groups obtained by substituting a hydrogen atom of these groups with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a fluorine atom, and the like.

[0031] The term "p-valent heterocyclic group" (p denotes an integer of 1 or more) means an atomic group remaining after removing from a heterocyclic compound p atoms of hydrogen among the hydrogen atoms that are directly bonded to carbon atoms or hetero atoms constituting the ring. Among p-valent heterocyclic groups, preferable are "p-valent aromatic heterocyclic groups", which are the atomic groups remaining after p atoms of hydrogen among the hydrogen atoms directly bonded to carbon atoms or hetero atoms constituting the ring are removed from an aromatic heterocyclic compound.

[0032] The term "aromatic heterocyclic compound" means, for example, a compound in which the heterocyclic ring itself exhibits aromaticity, such as oxadiazole, thiadiazole, thiazole, oxazole, thiophene, pyrrole, phosphole, furan, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole, dibenzophosphole, and the like, or a compound in which an aromatic ring is condensed to a heterocyclic ring even if the heterocyclic ring itself does not exhibit aromaticity, such as phenoxazine, phenothiazine, dibenzoborole, dibenzosilole, benzopyran, and the like.

[0033] The monovalent heterocyclic group usually has 2 to 60 carbon atoms, and preferably 4 to 20 carbon atoms, not including the carbon atoms of the substituent.

[0034] The monovalent heterocyclic group may have a substituent, and examples thereof include a thienyl group, a pyrrolyl group, a furyl group, a pyridyl group, a piperidinyl group, a quinolinyl group, an isoquinolinyl group, a pyrimidinyl group and a triazinyl group, and groups obtained by substituting a hydrogen atom of these groups with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, and the like.

[0035] The term "halogen atom" means a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0036] An "amino group" may have a substituent, and a substituted amino group is preferable. As the substituent that the amino group has, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group is preferable.

[0037] Examples of the substituted amino group include a dialkylamino group, a dicycloalkylamino group, and a diarylamino group.

[0038] Examples of the amino group include a dimethylamino group, a diethylamino group, a diphenylamino group, a bis(4-methylphenyl)amino group, a bis(4-tert-butylphenyl)amino group, and a bis(3,5-di-tert-butylphenyl)amino group.

[0039] An "alkenyl group" may be any of linear and branched. The linear alkenyl group usually has 2 to 30 carbon atoms, and preferably 3 to 20 carbon atoms, not including the carbon atoms of the substituent. The branched alkenyl group usually has carbon atoms 3 to 30, and preferably 4 to 20 carbon atoms, not including the carbon atoms of the substituent.

[0040] A "cycloalkenyl group" usually has 3 to 30 carbon atoms, and preferably 4 to 20 carbon atoms, not including the carbon atoms of the substituent.

[0041] The alkenyl group and the cycloalkenyl group each may have a substituent, and examples thereof include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 2-butenyl group, a 3-butenyl group, a 3-pentenyl group, a 4-pentenyl group, a 1-hexenyl group, a 5-hexenyl group, and a 7-octenyl group, and these groups having a substituent.

[0042] An "alkynyl group" may be any of linear and branched. The alkynyl group usually has 2 to 20 carbon atoms, and preferably 3 to 20 carbon atoms, not including the carbon atoms of the substituent. The branched alkynyl group usually has 4 to 30 carbon atoms, and preferably 4 to 20 carbon atoms, not including the carbon atoms of the substituent.

[0043] A "cycloalkynyl group" usually has 4 to 30 carbon atoms, and preferably 4 to 20 carbon atoms, not including the carbon atoms of the substituent.

[0044] The alkynyl group and the cycloalkynyl group each may have a substituent, and examples thereof include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 2-butynyl group, a 3-butynyl group, a 3-pentynyl group, a 4-pentynyl group, a 1-hexynyl group and a 5-hexynyl group, and these groups having a substituent.

[0045] An "arylene group" means an atomic group remaining after removing from an aromatic hydrocarbon two hydrogen atoms that are directly bonded to a carbon atom constituting the ring. The arylene group usually has 6 to 60 carbon atoms, preferably 6 to 30 carbon atoms, and more preferably 6 to 18 carbon atoms, not including the carbon atoms of the substituent.

[0046] The arylene group may have a substituent, and examples thereof include a phenylene group, a naphthalenediyl group, an anthracenediyl group, a phenanthrenediyl group, a dihydrophenanthrenediyl group, a naphthacenediyl group, a fluorenediyl group, a pyrenediyl group, a perylenediyl group, a chrysenediyl group, and these groups having a substituent, and preferable are groups represented by formulas (A-1) to (A-20). The arylene group may be a group obtained by bonding a plurality of these groups.







(Wherein R and Ra each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group; the plurality of R and Ra each may be the same or different at each occurrence; and the plurality of Ra may be bonded to each other to form a ring together with the atoms to which they are bonded.)

[0047] The divalent heterocyclic group usually has 2 to 60 carbon atoms, preferably 3 to 20 carbon atoms, and more preferably 4 to 15 carbon atoms, not including the carbon atoms of the substituent.

[0048] The divalent heterocyclic group may have a substituent, and examples thereof include divalent groups obtained by removing from pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilole, phenoxazine, phenothiazine, acridine, dihydroacridine, furan, thiophene, azole, diazole and triazole two hydrogen atoms among the hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting the ring. Preferable are groups represented by formulas (AA-1) to (AA-34). The divalent heterocyclic group may be a group obtained by bonding a plurality of these groups.















(Wherein R and Ra have the same meanings as described above.)

[0049] The term "crosslinkable group" means a group capable of producing a new bond when subjected to heat, UV-irradiation, near-UV irradiation, visible light irradiation, infrared irradiation, a radical reaction, and the like. Preferable are crosslinkable groups represented by formulas (XL-1) to (XL-17) of the group of crosslinkable groups A.

(Wherein RXL represents a methylene group, an oxygen atom, or a sulfur atom, and nXL denotes an integer of 0 to 5; when there are a plurality of RXL, they may be the same or different, and when there are a plurality of nXL, they may be the same or different; *1 represents a bonding position; and these crosslinkable groups each may have a substituent.)

[0050] The term "substituent" represents a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an amino group, a substituted amino group, an alkenyl group, a cycloalkenyl group, an alkynyl group, or a cycloalkynyl group. The substituent may also be a crosslinkable group.

<Phosphorescent Compound>



[0051] The term "phosphorescent compound" usually means a compound exhibiting phosphorescence at room temperature (25°C), and is preferably a compound that emits light at room temperature from a triplet excited state. This compound that emits light from a triplet excited state has a central metal atom and a ligand.

[0052] The central metal atom may be a metal atom having an atomic number of 40 or more, which has a spin-orbit interaction in the compound, and is capable of causing intersystem crossing between the singlet state and the triplet state. Examples of the metal atom include a rhodium atom, a palladium atom, an iridium atom, and a platinum atom.

[0053] The ligand may be a neutral or anionic monodentate ligand, or a neutral or anionic multidentate ligand, which forms at least one bond selected from the group consisting of a coordinate bond and a covalent bond with the central metal atom. Examples of the bond between the central metal atom and the ligand include a metal-nitrogen bond, a metal-carbon bond, a metal-oxygen bond, a metal-phosphorus bond, a metal-sulfur bond, and a metal-halogen bond. The term multidentate ligand usually means a ligand having two or more and six or less donor atoms.

[0054] The phosphorescent compound can be obtained from Aldrich, Luminescence Technology Corp., American Dye Source, and the like.

[0055] Further, the phosphorescent compound can also be obtained based on known methods described in the "Journal of the American Chemical Society, Vol. 107, 1431-1432 (1985)", "Journal of the American Chemical Society, Vol. 106, 6647-6653 (1984)", International Publication No. 2004/026886, International Publication No. 2006/121811, International Publication No. 2011/024761, and International Publication No. 2007/097153.

[0056] The maximum peak wavelength of the emission spectrum of the phosphorescent compound can be evaluated by dissolving the phosphorescent compound in an organic solvent such as xylene, toluene, chloroform, or tetrahydrofuran to prepare a dilute solution (1 × 10-6 to 1 × 10-3 % by mass), and measuring the PL spectrum of the dilute solution at room temperature. Xylene is preferable as the organic solvent for dissolving the phosphorescent compound.

<Phosphorescent Compound Represented by Formula (1)>



[0057] First, the phosphorescent compound represented by formula (1) contained in the composition according to the present embodiment is described.

[0058] The phosphorescent compound represented by formula (1) is constituted of M1, which is a central metal, a ligand whose number is defined by the suffix n1, and a ligand whose number is defined by the suffix n2.

[0059] M1 is preferably an iridium atom or a platinum atom, and more preferably an iridium atom, because the external quantum efficiency of the light-emitting device according to the present embodiment is better.

[0060] When M1 is a rhodium atom or an iridium atom, n1 is preferably 2 or 3, and more preferably 3.

[0061] When M1 is a palladium atom or a platinum atom, n1 is preferably 2.

[0062] E1 and E2 are preferably carbon atoms.

[0063] When the ring R1A is a diazole ring, it is preferably an imidazole ring in which E11A is a nitrogen atom or an imidazole ring in which E12A is a nitrogen atom, and more preferably the ring R1A is an imidazole ring in which E11A is a nitrogen atom.

[0064] When the ring R1A is a triazole ring, it is preferably a triazole ring in which E11A and E12A are nitrogen atoms.

[0065] When E11A is a nitrogen atom and R11A is present, R11A is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably an aryl group, or a monovalent heterocyclic group, still more preferably an aryl group, and these groups each may have a substituent.

[0066] When E11A is a carbon atom, R11A is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, still more preferably a hydrogen atom, an alkyl group, or a cycloalkyl group, and particularly preferably a hydrogen atom, and these groups each may have a substituent.

[0067] When E12A is a nitrogen atom and R12A is present, R12A is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, and still more preferably an aryl group, and these groups each may have a substituent.

[0068] When E12A is a carbon atom, R12A is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, still more preferably a hydrogen atom, an alkyl group, or a cycloalkyl group, and particularly preferably a hydrogen atom, and these groups each may have a substituent.

[0069] The aryl group in R11A and R12A is preferably a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a dihydrophenanthrenyl group, a fluorenyl group, or a pyrenyl group, more preferably a phenyl group, a naphthyl group or a fluorenyl group, and still more preferably a phenyl group, and these groups each may have a substituent.

[0070] Preferable examples of the monovalent heterocyclic group in R11A and R12A include a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a phenoxazinyl group, and a phenothiazinyl group, more preferable are a pyridyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, a carbazolyl group, an azacarbazolyl group, and a diazacarbazolyl group, and still more preferable are a pyridyl group, a pyrimidinyl group and a triazinyl group, and these groups each may have a substituent.

[0071] In the substituted amino group of R11A and R12A, the substituent possessed by the amino group is preferably an aryl group or a monovalent heterocyclic group, and these groups each may further have a substituent. The examples and preferable ranges of the aryl group in the substituent that the amino group has are the same as the examples and preferable ranges of the aryl group in R11A and R12A. The examples and preferable ranges of the monovalent heterocyclic group in the substituent that the amino group has are the same as the examples and preferable ranges of the monovalent heterocyclic group in R11A and R12A.

[0072] The optional substituents of R11A and R12A are preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, or a substituted amino group, more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, still more preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and particularly preferably an alkyl group or an aryl group, and these groups each may further have a substituent.

[0073] The aryl group, monovalent heterocyclic group, or substituted amino group in R11A and R12A is preferably a group represented by formula (D-A), (D-B), or (D-C), more preferably a group represented by formula (D-A) or (D-C), and still more preferably a group represented by formula (D-C), because the external quantum efficiency of the light-emitting device according to the present embodiment is better.

[0074] mDA1, mDA2, mDA3, mDA4, mDA5, mDA6, and mDA7 are generally an integer of 10 or less, preferably an integer of 5 or less, more preferably an integer of 2 or less, and still more preferably 0 or 1. It is preferable that mDA2, mDA3, mDA4, mDA5, mDA6, and mDA7 are the same integer, and it is more preferable that mDA1, mDA2, mDA3, mDA4, mDA5, mDA6, and mDA7 are the same integer.

[0075] GDA is preferably a group represented by formula (GDA-11) to (GDA-15), more preferably a group represented by formula (GDA-11) to (GDA-14), still more preferably a group represented by formula (GDA-11) or (GDA-14), and particularly preferably a group represented by formula (GDA-11).

(Wherein,

* represents a bond with ArDA1 in formula (D-A), ArDA1 in formula (D-B), ArDA2 in formula (D-B), or ArDA3 in formula (D-B),

** represents a bond with ArDA2 in formula (D-A), ArDA2 in formula (D-B), ArDA4 in formula (D-B), or ArDA6 in formula (D-B),

*** represents a bond with ArDA3 in formula (D-A), ArDA3 in formula (D-B), ArDA5 in formula (D-B), or ArDA7 in formula (D-B), and

RDA represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups each may further have a substituent; when there are a plurality of RDA, they may be the same or different.)



[0076] RDA is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, or a cycloalkoxy group, more preferably a hydrogen atom, an alkyl group, or a cycloalkyl group, and these groups each may have a substituent.

[0077] ArDA1, ArDA2, ArDA3, ArDA4, ArDA5, ArDA6, and ArDA7 are preferably a phenylene group, a fluorenediyl group, or a carbazolediyl group, more preferably a group represented by formula (A-1) to (A-3), (A-8), (A-9), (AA-10), (AA-11), (AA-33), or (AA-34), and still more preferably a group represented by formula (ArDA-1) to (ArDA-5), particularly preferably a group represented by formula (ArDA-1) to (ArDA-3), and especially preferably a group represented by formula (ArDA-1).

(Wherein RDA has the same meaning as described above,
RDB represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups each may have a substituent; and when there are a plurality of RDB, they may be the same or different.)

[0078] RDB is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, and still more preferably an aryl group, and these groups each may have a substituent.

[0079] TDA is preferably a group represented by formula (TDA-1) to (TDA-3), more preferably a group represented by formula (TDA-1).

(Wherein RDA and RDB have the same meanings as described above.)

[0080] The group represented by formula (D-A) is preferably a group represented by formula (D-A1) to (D-A4), more preferably a group represented by formula (D-A1) or (D-A4), and still more preferably a group represented by formula (D-A1).

[0081] The group represented by formula (D-B) is preferably a group represented by formula (D-B1) to (D-B3), and more preferably a group represented by formula (D-B1).

[0082] The group represented by formula (D-C) is preferably a group represented by formula (D-C1) to (D-C4), more preferably a group represented by formula (D-C1) to (D-C3), more preferably a group represented by formula (D-C1) or (D-C2), and particularly preferably a group represented by formula (D-C1).

[0083] np1 is preferably 0 or 1, more preferably 1. np2 is preferably 0 or 1, and more preferably 0. np3 is preferably 0. np4 is preferably an integer of 0 to 2. np 5 is preferably an integer of 1 to 3. np6 is preferably an integer of 0 to 2.

[0084] Rp1, Rp2, Rp3, Rp4, Rp5, and Rp6 are preferably an alkyl group or a cycloalkyl group, more preferably a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group, a cyclohexyl, a methoxy group, a 2-ethylhexyloxy group, a tert-octyl group or a cyclohexyloxy group, and still more preferably a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group, or a tert-octyl group.

[0085] Examples of the group represented by formula (D-A) include groups represented by formulas (D-A-1) to (D-A-12).



(Wherein,
RD represents a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group, a tert-octyl group, a cyclohexyl group, a methoxy group, a 2-ethylhexyloxy group, or a cyclohexyloxy group; when there are a plurality of RD, they may be the same or different.)

[0086] Examples of the group represented by formula (D-B) include groups represented by formulas (D-B-1) to (D-B-4).

(Wherein RD has the same meaning as described above.)

[0087] Examples of the group represented by formula (D-C) include groups represented by formulas (D-C-1) to (D-C-17).



(Wherein RD has the same meaning as described above.)

[0088] RD is preferably a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group, or a tert-octyl group.

[0089] To achieve a better external quantum efficiency of the light-emitting device according to the present embodiment, at least one selected from the group consisting of R11A and R12A is preferably an aryl group which may have a substituent or a monovalent heterocyclic group which may have a substituent, more preferably is an aryl group which may have a substituent, still more preferably is a group represented by formula (D-A1), (D-A4), (D-B1), or (D-C1) to (D-C4), particularly preferably a group represented by formula (D-C1) to (D-C3), especially preferably a group represented by formula (D-C1) or (D-C2), and even more especially preferably a group represented by formula (D-C1).

[0090] When at least one member selected from the group consisting of R11A and R12A is an aryl group which may have a substituent or a monovalent heterocyclic group which may have a substituent, it is preferable that R11A be an aryl group which may have a substituent or a monovalent heterocyclic group which may have a substituent, and it is more preferable that R11A be an aryl group which may have a substituent.

[0091] R11A and R12A may be bonded to each other to form a ring together with the atoms to which they are bonded, but because the maximum peak wavelength of the emission spectrum of the phosphorescent compound represented by formula (1) becomes a long wavelength, it is preferable not to form a ring.

[0092] R13A is preferably an aryl group or a monovalent heterocyclic group, and more preferably an aryl group, and these groups each may have a substituent.

[0093] The examples and preferable ranges of the aryl group, the monovalent heterocyclic group, and the substituted amino group in R13A are each the same as the examples and preferable ranges of the aryl group, the monovalent heterocyclic group, and the substituted amino group in R11A and R12A.

[0094] The examples and preferable ranges of the optional substituent of R13A are the same as the examples and preferable ranges of the optional substituents of R11A and R12A.

[0095] The ring R2 is preferably a 5-or 6-membered aromatic hydrocarbon ring or a 5-or 6-membered aromatic heterocyclic ring, more preferably a 6-membered aromatic hydrocarbon ring or a 6-membered aromatic heterocyclic ring, and still more preferably a 6-membered aromatic hydrocarbon ring, and these rings each may have a substituent. When the ring R2 is a 6-membered aromatic heterocyclic ring, E2 is preferably a carbon atom.

[0096] Examples of the ring R2 include a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, an indene ring, a pyridine ring, a diazabenzene ring, and a triazine ring, A benzene ring, a naphthalene ring, a fluorene ring, a pyridine ring, or a pyrimidine ring is preferable, a benzene ring, a pyridine ring, or a pyrimidine ring is more preferable, and a benzene ring is still more preferable, and these rings each may have a substituent.

[0097] The optional substituent of the ring R2 is preferably a fluorine atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, more preferably an alkyl group, a cycloalkyl group, an alkoxy group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, still more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, particularly preferably an alkyl group or a group represented by formula (D-A), (D-B), or (D-C), especially preferably a group represented by formula (D -D), (D-B) or (D-C), even more especially preferably a group represented by formula (D-A) or (D-C), and most preferably a group represented by (D-A), and these groups each may further have a substituent.

[0098] The examples and preferable ranges of the aryl group, the monovalent heterocyclic group, and the substituted amino group of the optional substituent of the ring R2 are each the same as the examples and preferable ranges of the aryl group, the monovalent heterocyclic group, and the substituted amino group in R11A and R12A.

[0099] The examples and preferable ranges of the substituent that the optional substituent of the ring R2 may further have are the same as the examples and preferable ranges of the optional substituents of R11A and R12A.

[Anionic Bidentate Ligand]



[0100] Examples of the anionic bidentate ligand represented by A1-G1-A2 include ligands represented by the following formulas.





(Wherein * represents a site that binds to M1.)

[0101] The anionic bidentate ligand represented by A1-G1-A2 may be a ligand represented by the following formulas. However, the anionic bidentate ligand represented by A1-G1-A2 is different from the ligand whose number is defined by the suffix n1.

(Wherein,

* represents a site that binds to M1,

RL1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, or a halogen atom, and these groups each may have a substituent; the plurality of RL1 may be the same or different, and

RL2 represents an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a halogen atom, and these groups each may have a substituent.)



[0102] RL1 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or a fluorine atom, and more preferably a hydrogen atom or an alkyl group, and these groups each may have a substituent.

[0103] RL2 is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, and still more preferably an aryl group, and these groups each may have a substituent.

[0104] To achieve a better external quantum efficiency of the light-emitting device according to the present embodiment, the phosphorescent compound represented by formula (1) is preferably a phosphorescent compound represented by formula (1-A).

[0105] When the ring R2A is a pyridine ring, a pyridine ring in which E21A is a nitrogen atom, a pyridine ring in which E22A is a nitrogen atom, or a pyridine ring in which E23A is a nitrogen atom is preferable, and a pyridine ring in which E22A is a nitrogen atom is more preferable.

[0106] When the ring R2A is a pyrimidine ring, a pyrimidine ring in which E21A and E23A are nitrogen atoms, or a pyrimidine ring in which E22A and E24A are nitrogen atoms is preferable, and a pyrimidine ring in which E22A and E24A are nitrogen atoms is more preferable.

[0107] The ring R2A is preferably a benzene ring.

[0108] R21A, R22A, R23A, and R24A are preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, and still more preferably a hydrogen atom, an alkyl group, or a group represented by formula (D-A), (D-B) or (D-C), particularly preferably a hydrogen atom or a group represented by formula (D-A), (D-B) or (D-C), especially preferably a hydrogen atom or a group represented by formula (D-A) or (D-C), and even more especially preferably a hydrogen atom or a group represented by formula (D-A), and these groups each may have a substituent.

[0109] The examples and preferable ranges of the aryl group, the monovalent heterocyclic group, and the substituted amino group in R21A, R22A, R23A, and R24A are each the same as the examples and preferable ranges of the aryl group, the monovalent heterocyclic group, and the substituted amino group of the optional substituent of the ring R2.

[0110] The examples and preferable ranges of the optional substituent of R21A, R22A, R23A, and R24A are the same as the examples and preferable ranges of the substituent that the optional substituent of the ring R2 may further have.

[0111] To achieve a better external quantum efficiency of the light-emitting device according to the present embodiment, at least one selected from the group consisting of R21A, R22A, R23A, and R24A is preferably a group represented by formula (D-A), (D-B), or (D-C), more preferably a group represented by formula (D-A) or (D-C), and still more preferably a group represented by formula (D-A).

[0112] When at least one member selected from the group consisting of R21A, R22A, R23A, and R24A is a group represented by formula (D-A), (D-B), or (D-C), it is preferable that R22A or R23A be a group represented by formula (D-A), (D-B), or (D-C), and more preferable that R22A be a group represented by formula (D-A), (D-B), or (D-C).

[0113] To achieve an even better external quantum efficiency of the light-emitting device according to the present embodiment, the phosphorescent compound represented by formula (1-A) is preferably a phosphorescent compound represented by formula (1-A1), a phosphorescent compound represented by formula (1-A2), a phosphorescent compound represented by formula (1-A3), or a phosphorescent compound represented by formula (1-A4), more preferably a phosphorescent compound represented by formula (1-A1) or a phosphorescent compound represented by formula (1-A3), and still more preferably a phosphorescent compound represented by formula (1-A1).

[0114] Examples of the phosphorescent compound represented by formula (1) include phosphorescent compounds represented by formulas (Ir-100) to (Ir-133), (Pt-100) to (Pt-104), (Pd-100), or (Rh-100), and the phosphorescent compounds represented by formulas (Ir-100) to (Ir-129), (Pt-100) to (Pt-104), (Pd-100), or (Rh-100) are preferable. In the formula, EA represents a group represented by -CH= or a group represented by -N=.










































<Method for Producing Phosphorescent Compound Represented by Formula (1)>



[0115] The phosphorescent compound represented by formula (1) can be produced by, for example, a method in which a compound serving as a ligand is reacted with a metal compound. Optionally, a functional group conversion reaction of the ligand of the phosphorescent compound may be carried out.

[0116] The phosphorescent compound represented by formula (1) can be produced by, for example, a step A of reacting a compound represented by formula (M-1) with a metal compound or a hydrate thereof, and a step B of reacting the compound obtained in step A (hereinafter also referred to as "phosphorescent compound intermediary (1)") with a compound represented by formula (M-1) or a precursor of a ligand represented by A1-G1-A2 (hereinafter also referred to as "production method 1").

(Wherein M1, n1, n2, the ring R1A, the ring R2, E1, E2, E11A, E12A, R11A, R12A, R13A, and A1-G1-A2 have the same meanings as described above.)

[0117] In step A, examples of the metal compound include iridium compounds such as iridium chloride, tris(acetylacetonato)iridium(III), a chloro(cyclooctadiene)iridium(I) dimer, and iridium(III) acetate; platinum compounds such as potassium chloroplatinate; palladium compounds such as palladium chloride and palladium acetate; and rhodium compounds such as rhodium chloride. Examples of hydrates of metal compounds include iridium chloride trihydrate and rhodium chloride trihydrate.

[0118] Examples of the phosphorescent compound intermediary (1) include a compound represented by formula (M-2).

(Wherein,

M1, the ring R1A, the ring R2, E1, E2, E11A, E12A, R11A, R12A, and R13A have the same meanings as described above, and

n1' represents 1 or 2. When M1 is a rhodium atom or an iridium atom, n1' is 2, and when M1 is a palladium atom or a platinum atom, n1' is 1.)



[0119] In step A, the compound represented by formula (M-1) is usually 2 to 20 moles with respect to 1 mole of the metal compound or its hydrate.

[0120] In step B, the amount of the compound represented by formula (M-1) or the precursor of the ligand represented by A1-G1-A2 is usually 1 to 100 moles with respect to 1 mole of the phosphorescent compound intermediate (1).

[0121] In step B, the reaction is preferably carried out in the presence of a silver compound such as silver trifluoromethanesulfonate. When a silver compound is used, its amount is usually 2 to 20 moles relative to 1 mole of the phosphorescent compound intermediate (1).

[0122] Next, the functional group conversion reaction (hereinafter also referred to as "production method 2") of the ligand of the phosphorescent compound represented by formula (1) will be described.

[0123] In production method 2, examples of the functional group conversion reaction include known coupling reactions that use a transition metal catalyst, such as the Suzuki reaction, Buchwald reaction, Stille reaction, Negishi reaction, and Kumada reaction.

[0124] Examples of the production method 2 may include a method including a step C of performing a coupling reaction between a compound represented by formula (M-3) and a compound represented by formula (M-4).

(Wherein,

M1, n1, n2, the ring R1A, the ring R2, E1, E2, E11A, E12A, R11A, R12A, R13A, and A1-G1-A2 have the same meanings as described above,

W1 represents a chlorine atom, a bromine atom or an iodine atom; when there are a plurality of W1, they may be the same or different,

nW1 denotes an integer of 1 or more and 10 or less,

Z1 represents an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups each may have a substituent, and

W2 represents a group selected from the group consisting of the group of substituents B.)


<Group of Substituents B>



[0125] A group represented by -B(ORC2)2 (wherein RC2 represents a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, and these groups each may have a substituent; and the plurality of RC2 may be the same or different, and may be connected to each other to form a ring structure together with the oxygen atom to which they are bonded);
a group represented by -BF3Q' (wherein Q' represents Li, Na, K, Rb, or Cs);
a group represented by -MgY' (wherein Y' represents a chlorine atom, a bromine atom, or an iodine atom);
a group represented by -ZnY" (wherein Y" represents a chlorine atom, a bromine atom, or an iodine atom); and
a group represented by -Sn(RC3)3 (wherein RC3 represents a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, and these groups each may have a substituent; and the plurality of RC3 may be the same or different, and may be connected to each other to form a ring structure together with the tin atom to which they are bonded.

[0126] Examples of the group represented by -B(ORC2)2 include groups represented by formulas (W-1) to (W-10).



[0127] W1 is preferably a bromine atom or an iodine atom, as this enables the coupling reaction to proceed more easily.

[0128] nW1 is preferably an integer of 1 to 5, more preferably 1 or 2, and still more preferably 1.

[0129] Z1 is preferably an aryl group or a monovalent heterocyclic group, and more preferably an aryl group, and these groups each may have a substituent.

[0130] The examples and preferable ranges of the aryl group and monovalent heterocyclic group of Z1 are each the same as the examples and preferable ranges of the aryl group and monovalent heterocyclic group of the optional substituent of the ring R2.

[0131] The examples and preferable ranges of the optional substituent of Z1 are the same as the examples and preferable ranges of the substituent that the optional substituent of the ring R2 may further have.

[0132] W2 is preferably a group represented by -B(ORC2)2, and more preferably a group represented by formula (W-7).

[0133] In the coupling reaction, in order to accelerate the reaction, a catalyst such as a palladium catalyst may be used. Examples of the palladium catalyst may include palladium acetate, bis(triphenylphosphine)palladium(II) dichloride, tetrakis(triphenylphosphine)palladium(0), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), and tris(dibenzylideneacetone)dipalladium(0).

[0134] The palladium catalyst may be used in combination with a phosphorus compound such as triphenylphosphine, tri(o-tolyl)phosphine, tri(tert-butyl)phosphine, tricyclohexylphosphine, and 1,1'-bis(diphenylphosphino)ferrocene.

[0135] When a palladium catalyst is used in the coupling reaction, the amount thereof is usually an effective amount, for example, with respect to 1 mole of the compound represented by formula (M-3), preferably 0.00001 to 10 moles in terms of palladium element.

[0136] In the coupling reaction, optionally, a palladium catalyst and a base may be used in combination.

[0137] The compound represented by formula (M-3) can be synthesized, for example, by a method including a step D in which a phosphorescent compound represented by formula (1) is reacted with a halogenating agent.

[0138] In step D, examples of the halogenating agent include N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, and the like.

[0139] In step D, the amount of the halogenating agent is usually 1 to 50 moles with respect to 1 mole of the phosphorescent compound represented by formula (1).

[0140] Steps A, B, C, and D are usually carried out in a solvent. Examples of the solvent include alcohol solvents such as methanol, ethanol, propanol, ethylene glycol, glycerin, 2-methoxyethanol, and 2-ethoxyethanol; ether solvents such as diethyl ether, tetrahydrofuran (THF), dioxane, cyclopentyl methyl ether, and diglyme; halogen type solvents such as methylene chloride and chloroform; nitrile type solvents such as acetonitrile and benzonitrile; hydrocarbon solvents such as hexane, decalin, toluene, xylene, and mesitylene; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide; acetone, dimethylsulfoxide, water, and the like.

[0141] In steps A, B, C, and D, the reaction time is usually 30 minutes to 200 hours, and the reaction temperature is usually between the melting point and the boiling point of the solvent present in the reaction system.

[0142] The compounds, catalysts, and solvents used in the reactions described in <Method for Producing Phosphorescent Compound Represented by Formula (1)> may be used singly or in combination of two or more.

<Phosphorescent Compound Represented by Formula (2)>



[0143] Next, the phosphorescent compound represented by formula (2) contained in the composition according to the present embodiment will be described.

[0144] The phosphorescent compound represented by formula (2) is a phosphorescent compound constituted of M2, which is a central metal, a ligand whose number is defined by the suffix n3, and a ligand whose number is defined by the suffix n4.

[0145] M2 is preferably an iridium atom or a platinum atom, and more preferably an iridium atom, because the external quantum efficiency of a light-emitting device comprising the composition according to the present embodiment is better.

[0146] When M2 is a rhodium atom or an iridium atom, n3 is preferably 2 or 3, and more preferably 3.

[0147] When M2 is a palladium atom or a platinum atom, n3 is preferably 2.

[0148] EL is preferably a carbon atom.

[0149] Ring L1 is preferably a 6-membered aromatic heterocyclic ring having 1 or more and 4 or less nitrogen atoms as constituent atoms, more preferably a 6-membered aromatic heterocyclic ring having 1 or more and 2 or less nitrogen atoms as constituent atoms.

[0150] Examples of the ring L1 include a pyridine ring, a diazabenzene ring, a quinoline ring, and an isoquinoline ring, a pyridine ring, a pyrimidine ring, a quinoline ring, or an isoquinoline ring is preferable, and a pyridine ring, a quinoline ring, or an isoquinoline ring is more preferable.

[0151] Ring L2 is preferably a 5- or 6-membered aromatic hydrocarbon ring or a 5- or 6-membered aromatic heterocyclic ring, more preferably a 6-membered aromatic hydrocarbon ring or a 6-membered aromatic heterocyclic ring, and still more preferably a 6-membered aromatic hydrocarbon ring. When the ring L2 is a 6-membered aromatic heterocyclic ring, EL is preferably a carbon atom.

[0152] Examples of the ring L2 include a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, an indene ring, a pyridine ring, a diazabenzene ring, a pyrrole ring, a furan ring, and a thiophene ring, preferably a benzene ring, a naphthalene ring, a fluorene ring, a pyridine ring, or a pyrimidine ring, more preferably a benzene ring, a pyridine ring, or a pyrimidine ring, and still more preferably a benzene ring.

[0153] At least one ring selected from the group consisting of the ring L1 and the ring L2 has a group represented by formula (1-T). The expression "at least one ring selected from the group consisting of the ring L1 and the ring L2 has a group represented by formula (1-T)" means that, among the plurality of rings, a part or all of the hydrogen atoms directly bonded to a carbon atom or a nitrogen atom forming at least one of the rings is substituted with a group represented by formula (1-T). In the phosphorescent compound represented by formula (2), when there are a plurality of rings L1 and L2 (i.e., when n3 is 2 or 3), of the plurality of rings L1 and L2, although it is only necessary for at least one ring to have a group represented by formula (1-T), it is preferable that all of the plurality of rings L1, all of the plurality of rings L2, or all of the plurality of rings L1 and L2 to have a group represented by formula (1-T). More preferably, all of the plurality of rings L1 or all of the plurality of rings L2 have a group represented by formula (1-T), and still more preferably all of the plurality of rings L2 have a group represented by formula (1-T).

[0154] When there are a plurality of groups represented by formula (1-T), they may be the same or different.

[0155] The ring L1 and the ring L2 may have another substituent different from the group represented by formula (1-T). The other substituent is preferably a cyano group, an alkenyl group, or a cycloalkenyl group, and these groups each may further have a substituent.

[0156] When the ring L1 has a plurality of other substituents, those substituents may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded.

[0157] When the ring L2 has a plurality of other substituents, those substituents may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded.

[0158] The other substituent(s) in the ring L1 and the other substituent(s) in the ring L2 may be bonded to each other to form a ring together with the atoms to which they are bonded.

[Group Represented by Formula (1-T)]



[0159] R1T is preferably an alkyl group, a cycloalkyl group, a halogen atom, an aryl group, a monovalent heterocyclic group, or a substituted amino group, more preferably an alkyl group, a cycloalkyl group, a fluorine atom, an aryl group, a monovalent heterocyclic group, or a substituted amino group, and still more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, and these groups each may have a substituent.

[0160] The examples and preferable ranges of the aryl group in R1T are the same as the examples and preferable ranges of the aryl group in R11A and R12A.

[0161] The examples and preferable ranges of the monovalent heterocyclic group in R1T are the same as the examples and preferable ranges of the monovalent heterocyclic group in R11A and R12A.

[0162] The examples and preferable ranges of the substituted amino group in R1T are the same as the examples and preferable ranges of the substituted amino group in R11A and R12A.

[0163] The examples and preferable ranges of the optional substituent of R1T are the same as the examples and preferable ranges of the optional substituent of R11A and R12A.

[0164] To achieve a better external quantum efficiency of a light-emitting device comprising the composition according to the present embodiment, R1T is preferably an alkyl group, a cycloalkyl group, or a group represented by formula (D-A), (D-B), or D-C), more preferably an alkyl group or a group represented by formula (D-A), (D-B), or (D-C), still more preferably an alkyl group or a group represented by formula (D-A) or (D-B), and even more preferably an alkyl group or a group represented by formula (D-A).

[0165] In the groups represented by formulas (D-A) and (D-B) in R1T, GDA is preferably a group represented by formulas (GDA-11) to (GDA-15), more preferably a group represented by formulas (GDA-11) to (GDA-14), and still more preferably a group represented by formula (GDA-11) or (GDA-14).

[0166] In R1T, the group represented by formula (D-A) is preferably a group represented by formulas (D-A1) to (D-A4), more preferably a group represented by formula (D-A1), (D-A3), or (D-A4), and still more preferably a group represented by formula (D-A1) or (D-A3).

[0167] In In R1T, the group represented by formula (D-B) is preferably a group represented by formulas (D-B1) to (D-B3), and more preferably a group represented by formula (D-B1) or (D-B3).

[0168] In R1T, the group represented by formula (D-C) is preferably a group represented by formulas (D-C1) to (D-C4), more preferably a group represented by formulas (D-C1) to (D-C3), still more preferably a group represented by formula (D-C1) or (D-C2), and particularly preferably a group represented by formula (D-C1).

[Anionic Bidentate Ligand]



[0169] Examples of the anionic bidentate ligand represented by A3-G2-A4 include ligands represented by the following formulas.



(Wherein, * represents a site that binds to M2.)

[0170] The anionic bidentate ligand represented by A3-G2-A4 may be a ligand represented by the following formulas.



(Wherein, * represents a site that binds to M2, and
RL1 and RL2 have the same meanings as described above.)

[0171] RL1 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or a fluorine atom, and more preferably a hydrogen atom or an alkyl group, and these groups each may have a substituent.

[0172] RL2 is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, and still more preferably an aryl group, and these group each may have a substituent.

[0173] To achieve a better external quantum efficiency of a light-emitting device comprising the composition according to the present embodiment, the phosphorescent compound represented by formula (2) is preferably a phosphorescent compound represented by formula (2-B).

[0174] When the ring L1B is a pyrimidine ring, a pyrimidine ring in which E11B is a nitrogen atom is preferable.

[0175] The ring L1B is preferably a pyridine ring.

[0176] When the ring L1B has a group represented by formula (1-T), R11B, R12B, or R13B is preferably the group represented by formula (1-T), more preferably R12B or R13B is the group represented by formula (1-T), and still more preferably R13B is the group represented by formula (1-T).

[0177] When the ring L2B is a pyridine ring, a pyridine ring in which E21B is a nitrogen atom, a pyridine ring in which E22B is a nitrogen atom, or a pyridine ring in which E23B is a nitrogen atom is preferable, and a pyridine ring in which E22B is a nitrogen atom is more preferable.

[0178] When the ring L2B is a pyrimidine ring, a pyrimidine ring in which E21B and E23B are nitrogen atoms or a pyrimidine ring in which E22B and E24B are nitrogen atoms is preferable, and a pyrimidine ring in which E22B and E24B are nitrogen atoms is more preferable.

[0179] The ring L2B is preferably a benzene ring.

[0180] When the ring L2B has a group represented by formula (1-T), R22B, R23B, or R24B is preferably the group represented by formula (1-T), and more preferably R22B or R23B is the group represented by formula (1-T).

[0181] To achieve an even better external quantum efficiency of a light-emitting device comprising the composition according to the present embodiment, the phosphorescent compound represented by formula (2-B) is preferably a phosphorescent compound represented by formula (2-B1), a phosphorescent compound represented by formula (2-B2), a phosphorescent compound represented by formula (2-B3), a phosphorescent compound represented by formula (2-B4), or a phosphorescent compound represented by formula (2-B5), and more preferably a phosphorescent compound represented by formula (2-B1), a phosphorescent compound represented by formula (2-B2), or a phosphorescent compound represented by formula (2-B3).

[0182] R15B, R16B, R17B, and R18B are preferably a hydrogen atom.

[0183] Examples of the phosphorescent compound represented by formula (2) include a phosphorescent compound represented by the following formulas.


























<Composition>



[0184] The composition according to the present embodiment is a composition comprising a phosphorescent compound represented by formula (1) and a phosphorescent compound represented by formula (2).

[0185] In the composition according to the present embodiment, one phosphorescent compound represented by formula (1) may be contained singly, or two or more of them may be contained. Further, the composition according to the present embodiment may comprise a single phosphorescent compound represented by formula (2), or two or more phosphorescent compounds. To achieve a better external quantum efficiency and a better luminance lifetime of a light-emitting device comprising the composition according to the present embodiment, the composition according to the present embodiment preferably comprises two or more phosphorescent compounds represented by formula (2).

[0186] When the composition according to the present embodiment comprises two or more phosphorescent compounds represented by formula (2), to achieve a better external quantum efficiency of a light-emitting device comprising the composition according to the present embodiment, it is preferable that at least one of the two or more phosphorescent compounds represented by formula (2) be a phosphorescent compound represented by formula (2) in which the group represented by formula (1-T) is an alkyl group.

[0187] When the composition according to the present embodiment comprises two or more phosphorescent compounds represented by formula (2), to achieve an even better external quantum efficiency of a light-emitting device comprising the composition according to the present embodiment, it is preferable that a combination of at least two phosphorescent compounds represented by formula (2) be a combination of two phosphorescent compounds represented by formula (2) in which the group represented by formula (1-T) is an alkyl group, or, a combination of a phosphorescent compound represented by formula (2) in which the group represented by formula (1-T) is an alkyl group and a phosphorescent compound represented by formula (2) in which the group represented by formula (1-T) is a group represented by formula (D-A), (D-B), or (D-C).

[0188] When the composition according to the present embodiment comprises two or more phosphorescent compounds represented by formula (2), to achieve a better luminance lifetime of a light-emitting device comprising the composition according to the present embodiment, it is preferable that at least one of the two or more phosphorescent compounds represented by formula (2) be a phosphorescent compound represented by formula (2) in which the group represented by formula (1-T) is a group represented by formula (D-A), (D-B), or (D-C), and more preferably at least one be a phosphorescent compound represented by formula (2) in which the group represented by formula (1-T) is a group represented by formula (D-A).

[0189] When the composition according to the present embodiment comprises two or more phosphorescent compounds represented by formula (2), to achieve a better luminance lifetime of a light-emitting device comprising the composition according to the present embodiment, it is preferable that a combination of at least two phosphorescent compounds represented by formula (2) be a combination of a phosphorescent compound represented by formula (2) in which the group represented by formula (1-T) is an alkyl group and a phosphorescent compound represented by formula (2) in which the group represented by formula (1-T) is a group represented by formula (D-A), (D-B), or (D-C), or, a combination of two phosphorescent compounds represented by formula (2) in which the group represented by formula (1-T) is a group represented by formula (D-A), (D-B), or (D-C), and more preferably is a combination of two phosphorescent compounds represented by formula (2) in which the group represented by formula (1-T) is a group represented by formula (D-A), (D-B), or (D-C).

[0190] In the composition according to the present embodiment, the emission color can be adjusted, even to a white color, by adjusting the ratio between the content of the phosphorescent compound represented by formula (1) and the content of the phosphorescent compound represented by formula (2).

[0191] The emission color of the light-emitting device can be confirmed by determining the chromaticity coordinates (CIE chromaticity coordinates) by measuring the luminescent chromaticity of the light-emitting device. A white emission color means, for example, that the X chromaticity coordinate is within a range of 0.25 to 0.55, and the Y chromaticity coordinate is within the range of 0.25 to 0.55.

[0192] From the viewpoint of adjusting the emission color of the light-emitting device comprising the composition according to the present embodiment (in particular, adjusting the emission color to white), the maximum peak wavelength of the emission spectrum of the phosphorescent compound represented by formula (1) is usually 380 nm or more and less than 495 nm, preferably 400 nm or more and 490 nm or less, more preferably 420 nm or more and 480 nm or less, and still more preferably 450 nm or more and 475 nm or less.

[0193] From the viewpoint of adjusting the emission color of the light-emitting device comprising the composition according to the present embodiment (in particular, adjusting the emission color to white), the maximum peak wavelength of the emission spectrum of the phosphorescent compound represented by formula (2) is usually 495 nm or more and less than 750 nm, preferably 500 nm or more and 680 nm or less, and more preferably 505 nm or more and 640 nm or less.

[0194] When the composition according to the present embodiment comprises two or more phosphorescent compounds represented by formula (2), from the viewpoint of adjusting the emission color of the light-emitting device comprising the composition according to the present embodiment (in particular, adjusting the emission color to white), the maximum peak wavelength of the emission spectrum of each of the at least two phosphorescent compounds represented by formula (2) is preferably different, and that difference is preferably 100 to 200 nm, more preferably 20 to 150 nm, and more preferably 40 to 120 nm.

[0195] When the composition according to the present embodiment comprises two or more phosphorescent compounds represented by formula (2), and, when the maximum peak wavelength of the emission spectrum of each of the at least two phosphorescent compounds represented by formula (2) is different, from the viewpoint of adjusting the emission color of the light-emitting device comprising the composition according to the present embodiment (in particular, adjusting the emission color to white), the maximum peak wavelength of the emission spectrum of the phosphorescent compound represented by formula (2) whose maximum peak wavelength of the emission spectrum is on the shorter wavelength side is preferably 500 nm or more and less than 570 nm, and more preferably 505 nm or more and 560 nm or less. Also, the maximum peak wavelength of the emission spectrum of the phosphorescent compound represented by formula (2) whose maximum peak wavelength of the emission spectrum is on the longer wavelength side is preferably 570 nm or more and 680 nm or less, and more preferably 590 nm or more and 640 nm or less.

[0196] From the viewpoint of adjusting the emission color of the light-emitting device comprising the composition according to the present embodiment (in particular, adjusting the emission color to white), the total content of the phosphorescent compound(s) represented by formula (2) is, based on 100 parts by mass for the total content of the phosphorescent compound(s) represented by formula (1), preferably 0.01 to 50 parts by mass, more preferably 0.05 to 30 parts by mass, still more preferably 0.1 to 10 parts by mass, and particularly preferably 0.5 to 5 parts by mass.

[0197] When the composition according to the present embodiment comprises two or more phosphorescent compounds represented by formula (2), and, when the maximum peak wavelength of the emission spectrum of each of the at least two phosphorescent compounds represented by formula (2) is different, of the two, the content of the phosphorescent compound represented by formula (2) whose maximum peak wavelength of the emission spectrum is the longer wavelength is, based on a content of the phosphorescent compound represented by formula (2) whose maximum peak wavelength of the emission spectrum is the shorter wavelength of 100 parts by mass, usually 1 to 10,000 parts by mass, and to achieve a better color reproducibility for a light-emitting device comprising the composition according to the present embodiment, this content is preferably 5 to 1000 parts by mass, and more preferably 10 to 200 parts by mass.

[0198] When the composition according to the present embodiment comprises two or more phosphorescent compounds represented by formula (2), to achieve a better external quantum efficiency of a light-emitting device comprising the composition according to the present embodiment, at least one of the phosphorescent compounds represented by formula (2) is preferably a phosphorescent compound represented by formulas (2-B1) to (2-B5), more preferably a phosphorescent compound represented by formulas (2-B1) to (2-B3), and still more preferably a phosphorescent compound represented by formula (2-B1).

[0199] When the composition according to the present embodiment comprises two or more phosphorescent compounds represented by formula (2), to achieve a better external quantum efficiency of a light-emitting device comprising the composition according to the present embodiment, a combination of at least two phosphorescent compounds represented by formula (2) is preferably a combination of two selected from the phosphorescent compounds represented by formulas (2-B1) to (2-B5), more preferably a combination of a phosphorescent compound represented by formula (2-B1) and one selected from the phosphorescent compounds represented by formulas (2-B2) to (2-B5), and still more preferably a combination of a phosphorescent compound represented by formula (2-B1) and a phosphorescent compound represented by formula (2-B2) or (2-B3).

<Other Components>



[0200] The composition according to the present embodiment may also further comprise at least one material selected from the group consisting of a hole transporting material, a hole injecting material, an electron transporting material, an electron injecting material, a light-emitting material (which is different from the phosphorescent compound represented by formula (1) and the phosphorescent compound represented by formula (2)), an antioxidant, and a solvent.

[Host Material]



[0201] By further comprising a host material having at least one function selected from hole injectability, hole transportability, electron injectability, and electron transportability in the composition according to the present embodiment, the external quantum efficiency of a light-emitting device comprising the composition according to the present embodiment is better. In the composition according to the present embodiment, one host material may be contained singly, or two or more of them may be contained.

[0202] When the composition according to the present embodiment further comprises a host material, the content of the host material is, based on 100 parts by mass for the total of the phosphorescent compound represented by formula (1), the phosphorescent compound represented by formula (2), and the host material, usually 1 to 99 parts by mass, preferably 10 to 90 parts by mass, more preferably 20 to 80 parts by mass, and still more preferably 50 to 75 parts by mass.

[0203] To achieve a better external quantum efficiency of a light-emitting device comprising the composition according to the present embodiment, a lowest excited triplet state (T1) of the host material is preferably an energy level equivalent to or higher than the lowest excited triplet state (T1) of the phosphorescent compound represented by formula (1).

[0204] The host material is classified into a low molecular weight compound and a polymer compound, and a low molecular weight compound is preferable.

[Low Molecular Weight Host]



[0205] Low molecular weight compounds (hereinafter referred to as "low molecular weight host") preferable as the host material will now be described.

[0206] The low molecular weight host is preferably a compound represented by formula (H-1).

[0207] ArH1 and ArH2 are preferably a phenyl group, a fluorenyl group, a spirobifluorenyl group, a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a thienyl group, a benzothienyl group, a dibenzothienyl group, a furyl group, a benzofuryl group, a dibenzofuryl group, a pyrrolyl group, an indolyl group, an azaindolyl group, a carbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a phenoxazinyl group, or a phenothiazinyl group, more preferably a phenyl group, a spirobifluorenyl group, a pyridyl group, a pyrimidinyl group, a triazinyl group, a dibenzothienyl group, a dibenzofuryl group, a carbazolyl group, or an azacarbazolyl group, still more preferably a phenyl group, a pyridyl group, a carbazolyl group, or an azacarbazolyl group, particularly preferably a group represented by formula (TDA-1) or (TDA-3), and especially preferably a group represented by formula (TDA-3), and these groups each may have a substituent.

[0208] The optional substituent of ArH1 and ArH2 is preferably a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, more preferably an alkyl group, a cycloalkyl group, an alkoxy group, or a cycloalkoxy group, and still more preferably an alkyl group or a cycloalkyl group is more preferable, and these groups each may further have a substituent.

[0209] nH1 is preferably 1. nH2 is preferably 0.

[0210] nH3 is usually an integer of 0 to 10, preferably an integer of 0 to 5, more preferably an integer of 1 to 3, and particularly preferably 1.

[0211] nH11 is preferably an integer of 1 or more and 5 or less, more preferably an integer of 1 or more and 3 or less, and still more preferably 1.

[0212] RH11 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably a hydrogen atom, an alkyl group, or a cycloalkyl group, and still more preferably a hydrogen atom or an alkyl group, and these groups each may have a substituent.

[0213] LH1 is preferably an arylene group or a divalent heterocyclic group.

[0214] LH1 is a compound represented by formula (A-1) to (A-3), (A-8) to (A-10), (AA-1) to (AA-6), (AA-10) to (AA-21), or (A-24) to (AA-34), more preferably a group represented by formula (A-1), (A-2), (A-8), (A-9), (AA-1) to (AA-4), (AA-10) to (AA-15), or (A-29) to (AA-34), still more preferably a group represented by formula (A-1), (A-2), (A-8), (A-9), (AA-2), (AA-4), or (AA-10) to (AA-15), particularly preferably a group represented by formula (A-1), (A-2), (A-8), (AA-2), (AA-4), (AA-10), (AA-12), or (AA-14), and especially preferably a group represented by formula (A-1), (A-2), (AA-2), (AA-4), or (AA-14).

[0215] The optional substituent of LH1 is preferably a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, more preferably an alkyl group, an alkoxy group, an aryl group, or a monovalent heterocyclic group, and still more preferably an alkyl group, an aryl group, or a monovalent heterocyclic group, and these groups each may further have a substituent.

[0216] LH21 is preferably a single bond or an arylene group, and more preferably a single bond, and the arylene group may have a substituent.

[0217] The definition and examples of the arylene group or divalent heterocyclic group represented by LH21 are the same as the definition and examples of the arylene group or divalent heterocyclic group represented by LH1.

[0218] RH21 is preferably an aryl group or a monovalent heterocyclic group, and these groups each may have a substituent.

[0219] The definition and examples of the aryl group or the monovalent heterocyclic group represented by RH21 are the same as the definition and examples of the aryl group or the monovalent heterocyclic group represented by ArH1 and ArH2.

[0220] The definition and examples of the optional substituent of RH21 are the same as the definitions and examples of the optional substituent of ArH1 and ArH2.

[0221] The compound represented by formula (H-1) is preferably a compound represented by formula (H-2).

(Wherein ArH1, ArH2, nH3, and LH1 have the same meanings as described above.)

[0222] Examples of the compound represented by formula (H-1) include the compounds represented by formulas (H-101) to (H-118).












[Polymer Host]



[0223] Examples of the polymer compound used for the host material include a polymer compound that serves as a hole transporting material (described later) and a polymer compound that serves as an electron transporting material (described later).

[0224] Polymer compound compounds that are preferable as the host material (hereinafter referred to as "polymer host") will now be described.

[0225] The polymer host is preferably a polymer compound comprising a constitutional unit represented by formula (Y).
[Chemical Formula 78]

        -[-ArY1-]-     (Y)



[0226] ArY1 represents an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded to each other, and these groups each may have a substituent.

[0227] The arylene group represented by ArY1 is more preferably an arylene group represented by formula (A-1), (A-2), (A-6) to (A-10), (A-19), or (A-20), and still more preferably a group represented by formula (A-1), (A-2), (A-7), (A-9), or (A-19), and these groups each may have a substituent.

[0228] More preferably, the divalent heterocyclic group represented by ArY1 is a group represented by formula (AA-1) to (AA-4), (AA-10) to (AA-15), (AA-18) to (AA-21), (AA-33), or (AA-34), and still more preferably a group represented by formula (AA-4), (AA-10), (AA-12), (AA-14), or (AA-33), and these groups each may have a substituent.

[0229] The more preferable range and still more preferable range of the arylene group and divalent heterocyclic group in the divalent group represented by ArY1 in which at least one arylene group and at least one divalent heterocyclic group are directly bonded to each other are respectively the same as the more preferable range and still more preferable range of the arylene group and divalent heterocyclic group represented by ArY1 described above.

[0230] Examples of the "divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded to each other" include groups represented by the following formulas, and these groups each may have a substituent.

(Wherein RXX represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups each may have a substituent.)

[0231] RXX is preferably an alkyl group, a cycloalkyl group, or an aryl group, and these groups each may have a substituent.

[0232] The optional substituent of the group represented by ArY1 is preferably an alkyl group, a cycloalkyl group, or an aryl group, and these groups each may further have a substituent.

[0233] Examples of the constitutional unit represented by formula (Y) include the constitutional units represented by formulas (Y-1) to (Y-10). From the viewpoint of achieving a better external quantum efficiency of the light-emitting device according to the present embodiment, the constitutional unit is preferably a constitutional unit represented by formulas (Y-1) to (Y-3). From the viewpoint of better electron transportability, the constitutional unit is preferably a constitutional unit represented by formulas (Y-4) to (Y-7). From the viewpoint of better hole transportability, the constitutional unit is preferably a constitutional unit represented by formulas (Y-8) to (Y-10).

(Wherein RY1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups each may have a substituent; and the plurality of RY1 may be the same or different and adjacent RY1 may be bonded to each other to form a ring together with the carbon atom to which they are bonded.)

[0234] RY1 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, and these groups each may have a substituent.

[0235] The constitutional unit represented by formula (Y-1) is preferably a constitutional unit represented by formula (Y-1').

(Wherein RY11 represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups each may have a substituent; and the plurality of RY11 may be the same or different.)

[0236] RY11 is preferably an alkyl group, a cycloalkyl group, or an aryl group, and more preferably an alkyl group or a cycloalkyl group, and these groups each may have a substituent.

(Wherein RY1 has the same meaning as described above; XY1 represents a group represented by -C(RY2)2-, -C(RY2)=C(RY2)-, or C(RY2)2-C(RY2)2-; RY2 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups each may have a substituent; and the plurality of RY2 may be the same or different, and RY2 may be bonded to another RY2 to form a ring together with the carbon atom to which they are bonded.)

[0237] RY2 is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and more preferably an alkyl group, a cycloalkyl group, or an aryl group, and these groups each may have a substituent.

[0238] In XY1, the combination of the two RY2 groups in the group represented by -C(RY2)2- is preferably a combination in which both groups are alkyl groups or cycloalkyl groups, a combination in which both groups are aryl groups, a combination in which both groups are monovalent heterocyclic groups, or a combination in which one group is an alkyl group or a cycloalkyl group and the other group is an aryl group or a monovalent heterocyclic group, and more preferably is a combination in which one group is an alkyl group or a cycloalkyl group and the other group is an aryl group, and these groups each may have a substituent. Two present RY2 groups may be bonded to each other to form a ring together with the atoms to which they are bonded. When RY2 forms a ring, the group represented by -C(RY2)2- is preferably a group represented by formulas (Y-A1) to (Y-A5), and more preferably a group represented by formula (Y-A4), and these groups each may have a substituent.



[0239] In XY1, the combination of the two RY2 groups in the group represented by -C(RY2)=C(RY2)- is preferably a combination in which both groups are alkyl groups or cycloalkyl groups or a combination in which one group is an alkyl group or a cycloalkyl group and the other group is an aryl group, and these groups each may have a substituent.

[0240] In XY1, the four RY2 in the group represented by -C(RY2)2-C(RY2)2- are preferably an optionally substituted alkyl group or cycloalkyl group. The plurality of RY2 may be bonded to each other to form a ring together with the atoms to which they are bonded, and when RY2 forms a ring, a group represented by -C(RY2)2-C(RY2)2- is preferably a group represented by formulas (Y-B1) to (Y-B5), and more preferably a group represented by formula (Y-B3), and these groups each may have a substituent.

(Wherein RY2 has the same meaning as described above.)

[0241] The constitutional unit represented by formula (Y-2) is preferably a constitutional unit represented by formula (Y-2').

(Wherein RY1 and XY1 have the same meanings as described above.)



(Wherein RY1 and XY1 have the same meanings as described above.)

[0242] The constitutional unit represented by formula (Y-3) is preferably a constitutional unit represented by formula (Y-3').

(Wherein RY11 and XY1 have the same meanings as described above.)



(Wherein RY1 has the same meaning as described above; RY3 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups each may have a substituent.)

[0243] RY3 is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and more preferably an aryl group, and these groups each may have a substituent.

[0244] The constitutional unit represented by formula (Y-4) is preferably a constitutional unit represented by formula (Y-4'), and the constitutional unit represented by formula (Y-6) is preferably a constitutional unit represented by formula (Y-6').

(Wherein RY1 and RY3 have the same meanings as described above.)

(Wherein RY1 has the same meaning as described above; RY4 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups each may have a substituent.)

[0245] RY4 is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and more preferably an aryl group. These groups each may have a substituent.

[0246] Examples of the constitutional unit represented by formula (Y) include constitutional units composed of arylene groups represented by formulas (Y-101) to (Y-121), constitutional units composed of divalent heterocyclic groups represented by formulas (Y-201) to (Y-206), and constitutional units composed of a divalent group represented by formulas (Y-300) to (Y-304) in which at least one arylene group and at least one divalent heterocyclic group are directly bonded to each other, and preferably constitutional units composed of arylene groups represented by formulas (Y-101) to (Y-121), constitutional units composed of divalent heterocyclic groups represented by formulas (Y-201) to (Y-206), and constitutional units composed of a divalent group represented by formulas (Y-301) to (Y-304) in which at least one arylene group and at least one divalent heterocyclic group are directly bonded to each other.

























[0247] To achieve a better external quantum efficiency of the light-emitting device according to the present embodiment, the content of the constitutional unit represented by formula (Y) in which ArY1 is an arylene group is preferably 0.5 to 90 mol%, and more preferably 30 to 80 mol%, based on the total amount of constitutional units contained in the polymer host.

[0248] To achieve better charge transportability of the light-emitting device according to the present embodiment, the content of the constitutional unit represented by formula (Y) in which ArY1 is a divalent heterocyclic group or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded to each other is preferably 0.5 to 40 mol%, and more preferably 3 to 30 mol%, based on the total amount of constitutional units contained in the polymer host.

[0249] Only one constitutional unit represented by formula (Y) may be contained or two or more of them may be contained in the polymer host.

[0250] To achieve better hole transportability, it is preferable that the polymer host further comprises a constitutional unit represented by formula (X).

(Wherein,

aX1 and aX2 each independently denote an integer of 0 or more,

ArX1 and ArX3 each independently represent an arylene group or a divalent heterocyclic group, and these groups each may have a substituent,

ArX2 and ArX4 each independently represent an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded to each other, and these groups each may have a substituent; and when there are a plurality of ArX2 and ArX4, they may be the same or different at each occurrence,

RX1, RX2, and RX3 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups each may have a substituent; and when there are a plurality of RX2 and RX3, they may be the same or different at each occurrence.)



[0251] aX1 is preferably 2 or less, and more preferably 1, because the external quantum efficiency of the light-emitting device according to the present embodiment is better.

[0252] aX2 is preferably 2 or less, and more preferably 0, because the external quantum efficiency of the light-emitting device according to the present embodiment is better.

[0253] RX1, RX2 and RX3 are preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and more preferably an aryl group, and these groups each may have a substituent.

[0254] The arylene group represented by ArX1 and ArX3 is more preferably a group represented by formula (A-1) or (A-9), and still more preferably a group represented by formula (A-1), and these groups each may have a substituent.

[0255] The divalent heterocyclic group represented by ArX1 and ArX3 is more preferably a group represented by formula (AA-1), (AA-2), or (AA-7) to (AA-26), and these groups each may have a substituent.

[0256] ArX1 and ArX3 are preferably an arylene group which may have a substituent.

[0257] The arylene group represented by ArX2 and ArX4 is more preferably an arylene group represented by formula (A-1), (A-6), (A-7), (A-9) to (A-11), or (A-19), and these groups each may have a substituent.

[0258] The more preferable range of the divalent heterocyclic group represented by ArX2 and ArX4 is the same as the more preferable range of the divalent heterocyclic group represented by ArX1 and ArX3.

[0259] The more preferable range and still more preferable range of the arylene group and the divalent heterocyclic group in the divalent group represented by ArX2 and ArX4 in which at least one arylene group and at least one divalent heterocyclic group are directly bonded to each other are respectively the same as the more preferable range and still more preferable range of the arylene group and the divalent heterocyclic group represented by ArX1 and ArX3.

[0260] Examples of the divalent group represented by ArX2 and ArX4 in which at least one arylene group and at least one divalent heterocyclic group are directly bonded to each other include the same divalent groups represented by ArY1 of formula (Y) in which at least one arylene group and at least one divalent heterocyclic group are directly bonded to each other.

[0261] ArX2 and ArX4 are preferably an arylene group which may have a substituent.

[0262] The optional substituent of the groups represented by ArX1 to ArX4 and RX1 to RX3 is preferably an alkyl group, a cycloalkyl group, or an aryl group, and these groups each may further have a substituent.

[0263] The constitutional unit represented by formula (X) is preferably a constitutional unit represented by formulas (X-1) to (X-7), more preferably a constitutional unit represented by formulas (X-1) to (X-6), and still more preferably a constitutional unit represented by formulas (X-3) to (X-6).









(Wherein, RX4 and RX5 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a halogen atom, a monovalent heterocyclic group, or a cyano group, and these groups each may have a substituent; the plurality of RX4 may be the same or different; and the plurality of RX5 may be the same or different, and adjacent RX5 may be bonded to each other to form a ring together with the carbon atom to which they are bonded.)

[0264] To achieve better hole transportability, the content of the constitutional unit represented by formula (X) is preferably 0.1 to 50 mol%, more preferably 1 to 40 mol%, and still more preferably 5 to 30 mol%, based on the total amount of constitutional units contained in the polymer host.

[0265] Examples of the constitutional unit represented by formula (X) include constitutional units represented by formulas (X1-1) to (X1-11). The constitutional unit represented by formula (X) is preferably a constitutional unit represented by formulas (X1-3) to (X1-10).











[0266] In the polymer host, only one constitutional unit represented by formula (X) may be contained or two or more of them may be contained.

[0267] Examples of the polymer host include the polymer compounds (P-1) to (P-6) in Table 1.
[Table 1]
Polymer CompoundConstitutional units and Molar Ratios Thereof
Formula (Y)Formula (X)Other
Formula (Y-1) to (Y-3)Formula (Y-4) to (Y-7)Formula (Y-8) to (Y-10)Formula (X-1) to (Y-7)
pqrst
(P-1) 0.1-99.9 0.1-99.9 0 0 0-30
(P-2) 0.1-99.9 0 0.1-99.9 0 0-30
(P-3) 0.1-99.8 0.1-99.8 0 0.1-99.8 0-30
(P-4) 0.1-99.8 0.1-99.8 0.1-99.8 0 0-30
(P-5) 0.1-99.8 0 0.1-99.8 0.1-99.8 0-30
(P-6) 0.1-99.7 0.1-99.7 0.1-99.7 0.1-99.7 0-30


[0268] In Table 1, p, q, r, s, and t represent the molar ratio of each constitutional unit, p + q + r + s + t = 100 and 100 ≥ p + q + r + s ≥ 70, the heading "Other" means a constitutional unit other than the constitutional unit represented by formula (Y) and the constitutional unit represented by formula (X).

[0269] The polymer host may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, or may even be some other form, but it is preferable that the polymer host is a copolymer obtained by copolymerizing a plurality of raw material monomers.

[Method for Producing Polymer host]



[0270] The polymer host can be produced by using a known polymerization method described in Chem. Rev., Vol. 109, pp. 897-1091 (2009) and the like. Examples of such a method include a polymerization method by a coupling reaction using a transition metal catalyst, such as in a Suzuki reaction, a Yamamoto reaction, a Buchwald reaction, a Stille reaction, a Negishi reaction, or a Kumada reaction.

[0271] In the polymerization method, examples of the method for charging the monomers may include a method in which all the monomers are charged all at once into the reaction system, a method in which a part of the monomers is charged and made to react, and then the remaining monomers are charged all at once, continuously, or in several stages, and a method in which the monomers are charged continuously or in several stages.

[0272] Examples of the transition metal catalyst include a palladium catalyst, a nickel catalyst and the like.

[0273] Workup is carried out by known methods, for example, a method in which water-soluble impurities are removed by liquid separation and a method in which a lower alcohol such as methanol is added to a reaction liquid after a polymerization reaction, and deposited sediments are filtered out and then dried, used singly or in combination. When the purity of the polymer host is low, the polymer host can be purified by a common method, for example, recrystallization, reprecipitation, continuous extraction with a Soxhlet extractor, column chromatography, and the like.

[Hole Transporting Material]



[0274] The hole transporting material is classified into a low molecular weight compound and a polymer compound, and a polymer compound is preferable. The hole transporting material may have a crosslinkable group.

[0275] Examples of the low molecular weight compounds include aromatic amine compounds such as triphenylamine and derivatives thereof, N,N'-di-1-naphthyl-N,N'-diphenylbenzidine (α-NPD), and N,N'-diphenyl-N,N'-di(m-tolyl)benzidine (TPD).

[0276] Examples of the polymer compounds include polyvinylcarbazole and derivatives thereof; and polyarylene having an aromatic amine structure in a side chain or main chain and derivatives thereof. The polymer compound may be a compound to which an electron accepting site is bound. Examples of the electron accepting moiety include fullerene, tetrafluorotetracyanoquinodimethane, tetracyanoethylene, trinitrofluorenone and the like, and fullerene is preferable.

[0277] When the composition according to the present embodiment comprises the hole transporting material, the amount of the hole transporting material is, based on 100 parts by mass for the total of the phosphorescent compound represented by formula (1) and the phosphorescent compound represented by formula (2), usually 1 to 400 parts by mass, and preferably 5 to 150 parts by mass.

[0278] One hole transporting material may be used alone, or two or more hole transporting materials may be used in combination.

[Electron Transporting Material]



[0279] The electron transporting materials are classified into a low molecular weight compound and a polymer compound. The electron transporting material may have a crosslinkable group.

[0280] Examples of the low molecular weight compound include metal complexes having 8-hydroxyquinoline as a ligand, oxadiazole, anthraquinodimethane, benzoquinone, naphthoquinone, anthraquinone, tetracyanoanthraquinodimethane, fluorenone, diphenyldicyanoethylene, and diphenoquinone, and derivatives of these.

[0281] Examples of the polymer compound include polyphenylene, polyfluorene, and derivatives thereof. The polymer compound may be doped with a metal.

[0282] When the composition according to the present embodiment comprises the electron transporting material, the amount of the electron transporting material blended is, based on 100 parts by mass for the total of the phosphorescent compound represented by formula (1) and the phosphorescent compound represented by formula (2), usually 1 to 400 parts by mass, and preferably 5 to 150 parts by mass.

[0283] One electron transporting material may be used alone, or two or more hole transporting materials may be used in combination.

[Hole Injecting Material and Electron Injecting Material]



[0284] The hole injecting material and the electron injecting material are each classified into a low molecular weight compound and a polymer compound. The hole injecting material and the electron injecting material may have a crosslinkable group.

[0285] Examples of the low molecular weight compound include metal phthalocyanines such as copper phthalocyanine; carbon; metal oxides of molybdenum, tungsten, and the like; and metal fluorides such as lithium fluoride, sodium fluoride, cesium fluoride, and potassium fluoride.

[0286] Examples of the polymer compound include conductive polymers such as polyaniline, polythiophene, polypyrrole, polyphenylenevinylene, polythienylenevinylene, polyquinoline, and polyquinoxaline, and derivatives of these; and polymers comprising an aromatic amine structure in the main chain or side chain.

[0287] When the composition according to the present embodiment comprises the hole injecting material and the electron injecting material, the amount of the hole injecting material and the electron injecting material blended is respectively, based on 100 parts by mass for the total of the phosphorescent compound represented by formula (1) and the phosphorescent compound represented by formula (2), usually 1 to 400 parts by mass, and preferably 5 to 150 parts by mass.

[0288] One of each of the electron transporting material and the hole transporting material may be used alone, or two or more of each of the electron transporting material and the hole transporting material may be used in combination.

[Ion Doping]



[0289] When the hole injecting material or the electron injecting material comprises a conductive polymer, the electrical conductivity of the conductive polymer is preferably 1 × 10-5 S/cm to 1 × 103 S/cm. The conductive polymer can be doped with an appropriate amount of ions in order to set the electrical conductivity of the conductive polymer in such a range.

[0290] The type of ion to be doped is an anion for the hole injecting material and a cation for the electron injecting material. Examples of the anion include polystyrenesulfonic acid ions, alkylbenzenesulfonic acid ions, and camphorsulfonic acid ions. Examples of the cation include lithium ions, sodium ions, potassium ions, and tetrabutylammonium ions.

[0291] One type of ion to be doped may be used alone, or two or more types of ion to be doped may be used.

[Light-Emitting Material]



[0292] The light-emitting material (which is different from the phosphorescent compound represented by formula (1) and the phosphorescent compound represented by formula (2)) is classified into a low molecular weight compound and a polymer compound. The light-emitting material may have a crosslinkable group.

[0293] Examples of the low molecular weight compound include phosphorescent compounds such as naphthalene and derivatives thereof, anthracene and derivatives thereof, perylene and derivatives thereof, as well as a phosphorescent compound (hereinafter also referred to as "another phosphorescent compound") different from the phosphorescent compound represented by formula (1) and the phosphorescent compound represented by formula (2). Examples of the another phosphorescent compound include a phosphorescent compound having iridium, platinum, or europium as a central metal atom.

[0294] Examples of the polymer compound include a polymer compound comprising a phenylene group, a naphthalenediyl group, a fluorenediyldiyl group, a phenanthrenediyl group, a dihydrophenanthrenediyl group, a group represented by formula (X), a carbazolediyl group, a phenoxazinediyl group, a phenothiazinediyl group, an anthracenediyl group, a pirenediyl group, and the like.

[0295] The light-emitting material is preferably the another phosphorescent compound.

[0296] Examples of the another phosphorescent compound include the compounds shown below.











[0297] In the composition according to the present embodiment, the content of the light-emitting material is, based on 100 parts by mass for the total of the phosphorescent compound represented by formula (1) and the phosphorescent compound represented by formula (2), usually 0.001 to 10 parts by mass.

[Antioxidant]



[0298] The antioxidant may be any compound that is soluble in the same solvent as the phosphorescent compound represent by formula (1) and the phosphorescent compound represent by formula (2), and that does not inhibit light emission and charge transporting. Examples of the antioxidant include a phenol type antioxidant and a phosphorus type antioxidant.

[0299] In the composition according to the present embodiment, the content of the antioxidant blended is, based on 100 parts by mass for the total of the phosphorescent compound represented by formula (1) and the phosphorescent compound represented by formula (2), usually 0.001 to 10 parts by mass.

[0300] One antioxidant may be used alone, or two or more antioxidants may be used in combination.

<Ink>



[0301] The composition according to the present embodiment may also comprise a solvent. Hereinafter, the solvent-comprising composition according to the present embodiment is referred to as an "ink".

[0302] The ink according to the present embodiment can be suitably used in a coating method such as spin coating, casting, micro gravure coating, gravure coating, bar coating, roll coating, wire bar coating, dip coating, spray coating, screen printing, flexographic printing, an offset printing method, ink jet printing, capillary coating, and nozzle coating.

[0303] The viscosity of the ink according to the present embodiment may be adjusted according to the type of coating method. However, when a solution of an ink jet printing method is applied in a printing method that employs an ejection apparatus, the viscosity is preferably 1 to 30 mPa·s at 25°C in order to prevent clogging and curved flight during ejection.

[0304] The solvent contained in the ink according to the present embodiment is preferably a solvent capable of dissolving or uniformly dispersing the solid content in the ink. Examples of the solvent include chlorinated solvents such as 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, and o-dichlorobenzene; ether solvents such as THF, dioxane, anisole, and 4-methylanisole; aromatic hydrocarbon solvents such as toluene, xylene, mesitylene, ethylbenzene, n-hexylbenzene, and cyclohexylbenzene; aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane, n-dodecane, and bicyclohexyl; ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone, and acetophenone; ester solvents such as ethyl acetate, butyl acetate, ethyl cellosolve acetate, methyl benzoate, and phenyl acetate; polyhydric alcohol solvents such as ethylene glycol, glycerin, and 1,2-hexanediol; alcohol solvents such as isopropyl alcohol and cyclohexanol; and sulfoxide solvents such as dimethylsulfoxide; amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide. One solvent may be used alone, or two or more solvents may be used in combination.

[0305] In the ink according to the present embodiment, the content of the solvent blended is, based on 100 parts by mass for the total of the phosphorescent compound represented by formula (1) and the phosphorescent compound represented by formula (2), usually 1000 to 100000 parts by mass, and preferably 2000 to 20000.

[0306] The ink according to the present embodiment may include a component other than the phosphorescent compound represented by formula (1), the phosphorescent compound represented by formula (2), and the solvent. For example, the ink according to the present embodiment can further include at least one material selected from the group consisting of the above-mentioned host material, hole transporting material, hole injecting material, electron transporting material, electron injecting material, light-emitting material (which is different from the phosphorescent compound represented by formula (1) and the phosphorescent compound represented by formula (2)), and antioxidant.

<Film>



[0307] The film comprises a phosphorescent compound represented by formula (1) and a phosphorescent compound represented by formula (2).

[0308] The film is suitable as a light-emitting layer in a light-emitting device.

[0309] The film can be produced by using the ink according to the present embodiment in a coating method such as spin coating, casting, micro gravure coating, gravure coating, bar coating, roll coating, wire bar coating, dip coating, spray coating, screen printing, flexographic printing, an offset printing method, ink jet printing, capillary coating, and nozzle coating.

[0310] The thickness of the film is usually 1 nm to 10 µm.

<Light-Emitting Device>



[0311] The light-emitting device according to the present embodiment is a light-emitting device comprising the composition according to the present embodiment.

[0312] The light-emitting device according to the present embodiment includes, for example, an anode, a cathode, and a layer comprising the composition according to the present embodiment provided between the anode and the cathode.

[Layer Structure]



[0313] The layer comprising the composition according to the present embodiment is usually one or more layers of the light-emitting layer, the hole transporting layer, the hole injecting layer, the electron transporting layer, and the electron injecting layer, and preferably the light-emitting layer. Each of these layers comprises the light-emitting material, the hole transporting material, the hole injecting material, the electron transporting material, and the electron injecting material. Examples of the method for forming these layers include, when using a low molecular weight compound, for example, a vacuum evaporation method from a powder and a film-formation method from a solution or a melted state can be cited, and when using a polymer compound, for example, a film-formation method from a solution or a melted state. Each layer can be formed, for example, by dissolving the light-emitting material, the hole transporting material, the hole injecting material, the electron transporting material, and the electron injecting material in the above-mentioned solvent to prepare an ink-state composition, and then using the ink-state composition to form the layers by the same coating method as for producing the above-mentioned film.

[0314] A light-emitting device has a light-emitting layer between an anode and a cathode. From the viewpoints of hole injectability and the hole transportability, the light-emitting device according to the present embodiment preferably has at least one layer hole injecting layer and at least one hole transporting layer between the anode and the light-emitting layer, and from the viewpoints of electron injectability and electron transportability, preferably has at least one electron injecting layer and at least one electron transporting layer between the cathode and the light-emitting layer.

[0315] Examples of the materials for the hole transporting layer, the electron transporting layer, the light-emitting layer, the hole injecting layer and the electron injecting layer include, in addition to the composition according to the present embodiment, each of the various hole transporting materials, electron transporting materials, light-emitting materials, hole injecting materials, and electron injecting materials described above.

[0316] When the material of the hole transporting layer, the material of the electron transporting layer, and the material of the light-emitting layer each dissolve in the solvent used when forming the layer adjacent to the hole transporting layer, the electron transporting layer, and the light-emitting layer, in order to avoid those materials dissolving in the solvent during the production of the light-emitting device, those materials preferably have a crosslinkable group. By forming the layers using a material having a crosslinkable group and then crosslinking the crosslinkable group, the layers can be made insoluble.

[0317] The order and number of layers to be laminated and the thickness of each layer can be adjusted in consideration of luminous efficiency, luminance lifetime, and the like.

[0318] When the light-emitting device according to the present embodiment comprises a hole transporting layer, the hole transporting material used to form the hole transporting layer is preferably a polymer compound (hereinafter also referred to as "polymer compound of the hole transporting layer") including a constitutional unit represented by formula (X) and at least one constitutional unit selected from the group consisting of a constitutional unit represented by formula (3) and a constitutional unit represented by formula (4). The polymer compound of the hole transporting layer may further comprise a constitutional unit represented by formula (Y).

[0319] When the light-emitting device according to the present embodiment comprises a hole transporting layer obtained using the polymer compound of the hole transporting layer, the polymer compound of the hole transporting layer may be contained in the hole transporting layer as is, or in an intramolecularly, an intermolecularly, or an intramolecularly and intermolecularly crosslinked state (i.e., as a crosslinked product). However, the hole transporting layer is preferably a layer comprising a crosslinked product of the polymer compound of the hole transporting layer. The crosslinked product of the polymer compound of the hole transporting layer may be a product in which the polymer compound of the hole transporting layer and another material are intermolecularly crosslinked.

[0320] To achieve better hold transportability of the polymer compound of the hole transporting layer, the content of the constitutional unit represented by formula (X) is preferably 1 to 99 mol%, more preferably 10 to 80 mol%, and still more preferably 20 to 70 mol%, based on the total amount of constitutional units contained in the polymer compound of the hole transporting layer.

[Constitutional unit Represented by Formula (3)]



[0321] 



(Wherein,

nA denotes an integer of 0 to 5, and n denotes an integer of 1 to 4,

Ar1 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups each may have a substituent,

LA represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -NR'-, an oxygen atom, or a sulfur atom, and these groups each may have a substituent; R' represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups each may have a substituent; and when there are a plurality of LA, they may be the same or different.

X represents a crosslinkable group selected from the group of crosslinkable group A; and when there are a plurality of X, they may be the same or different.)



[0322] To achieve a better external quantum efficiency of the light-emitting device according to the present embodiment, nA preferably denotes an integer of 0 to 3, more preferably an integer of 0 to 2, and still more preferably 1 or 2.

[0323] To achieve a better external quantum efficiency of the light-emitting device according to the present embodiment, n is preferably 2.

[0324] To achieve a better external quantum efficiency of the light-emitting device according to the present embodiment, Ar1 is preferably an aromatic hydrocarbon group that may have a substituent.

[0325] The aromatic hydrocarbon group represented by Ar1 usually has 6 to 60 carbon atoms, preferably 6 to 30 carbon atoms, and more preferably 6 to 18 carbon atoms, not including the carbon atoms of the substituent.

[0326] The arylene group moiety excluding the n substituents of the aromatic hydrocarbon group represented by Ar1 is preferably a group represented by formulas (A-1) to (A-20), more preferably a group represented by formula (A-1), (A-2), (A-6) to (A-10), (A-19), or (A-20), and still more preferably a group represented by formula (A-1), (A-2), (A-7), (A-9), or (A-19), and these groups each may have a substituent.

[0327] The heterocyclic group represented by Ar1 usually has 2 to 60 carbon atoms, preferably 3 to 30 carbon atoms, and more preferably 4 to 18 carbon atoms, not including the carbon atoms of the substituent.

[0328] The divalent heterocyclic group moiety excluding the n substituents of the heterocyclic group represented by Ar1 is preferably a group represented by formulas (AA-1) to (AA-34).

[0329] The aromatic hydrocarbon group and the heterocyclic group represented by Ar1 each may have a substituent. Examples of the substituent include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a halogen atom, a monovalent heterocyclic group, or a cyano group.

[0330] The alkylene group represented by LA usually has 1 to 20 carbon atoms, preferably 1 to 15 carbon atoms, and more preferably 1 to 10 carbon atoms, not including the carbon atoms of the substituent. The cycloalkylene group represented by LA usually has 3 to 20 carbon atoms, not including the carbon atoms of the substituent.

[0331] The alkylene group and the cycloalkylene group each may have a substituent, and examples thereof include a methylene group, an ethylene group, a propylene group, a butylene group, a hexylene group, a cyclohexylene group, and an octylene group.

[0332] The alkylene group and the cycloalkylene group represented by LA each may have a substituent.

[0333] Examples of the optional substituents of the alkylene group and the cycloalkylene group include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a halogen atom, and a cyano group.

[0334] The arylene group represented by LA may have a substituent. The arylene group is preferably a phenylene group or a fluorenediyl group, and more preferably an m-phenylene group, a p-phenylene group, a fluorene-2,7-diyl group, or a fluorene-9,9-diyl group. Examples of the optional substituent of the arylene group include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a halogen atom, a cyano group, and a crosslinkable group selected from the group of crosslinkable group A.

[0335] To facilitate synthesis of the polymer compound of the hole transporting layer, LA is preferably an arylene group or an alkylene group, and more preferably a phenylene group, a fluorenediyl group, or an alkylene group, and these groups each may have a substituent.

[0336] To achieve better crosslinking properties of the polymer compound of the hole transporting layer, the crosslinkable group represented by X is preferably a crosslinkable group represented by formula (XL-1), (XL-3), (XL-7) to (XL-10), (XL-16), or (XL-17), more preferably a crosslinkable group represented by formula (XL-1), (XL-3), (XL-9,) (XL-16), or (XL-17), still more preferably a crosslinkable group represented by formula (XL-1), (XL-16), or (XL-17), and particularly preferably a crosslinkable group represented by formula (XL-1) or (XL-17).

[0337] To achieve better crosslinking properties of the polymer compound of the hole transporting layer, the content of the constitutional unit represented by formula (3) is preferably 0.5 to 90 mol%, more preferably 3 to 75 mol%, still more preferably 5 to 60 mol%, based on the total amount of constitutional units contained in the polymer compound of the hole transporting layer.

[0338] Only one constitutional unit represented by formula (3) may be contained or two or more of them may be contained in the polymer compound of the hole transporting layer.

[Constitutional unit Represented by Formula (4)]



[0339] 

(Wherein,

mA denotes an integer of 0 to 5, m denotes an integer of 1 to 4, and c represents an integer of 0 or 1; and when there are a plurality of mA, they may be the same or different,

Ar3 represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocyclic ring are directly bonded to each other, and these groups may each have a substituent,

Ar2 and Ar4 each independently represent an arylene group or a divalent heterocyclic group, and these groups each may have a substituent,

Ar2, Ar3, and Ar4 may each be bonded either directly or via an oxygen atom or a sulfur atom to a group other than the group bonded to the nitrogen atom to which that group is bonded to form a ring,

KA represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -NR"-, an oxygen atom, or a sulfur atom, and these groups each may have a substituent; R" represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups each may have a substituent; and when there are a plurality of KA, they may be the same or different,

X' represents a crosslinkable group selected from the group of crosslinkable group A, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups each may have a substituent; however, at least one X' is a crosslinkable group selected from the group of crosslinkable group A.)



[0340] To achieve a better external quantum efficiency of the light-emitting device according to the present embodiment, mA is preferably 0 or 1, and more preferably 0.

[0341] To achieve a better external quantum efficiency of the light-emitting device according to the present embodiment, m is preferably 0.

[0342] To facilitate synthesis of the polymer compound of the hole transporting layer, and achieve a better external quantum efficiency of the light-emitting device according to the present embodiment, c is preferably 0.

[0343] To achieve a better external quantum efficiency of the light-emitting device according to the present embodiment, Ar3 is preferably an aromatic hydrocarbon group which may have a substituent.

[0344] The definition and examples of the arylene group moiety excluding the m substituents of the aromatic hydrocarbon group represented by Ar3 are the same as the definition and examples of the arylene group represented by ArX2 in the above-mentioned formula (X).

[0345] The definition and examples of the divalent heterocyclic group moiety excluding the m substituents of the heterocyclic group represented by Ar3 are the same as the definition and examples of the divalent heterocyclic group moiety represented by ArX2 in the above-mentioned formula (X).

[0346] The definition and examples of the divalent group excluding the m substituents of the group represented by Ar3 in which at least one aromatic hydrocarbon ring and at least one heterocyclic ring are directly bonded to each other are the same as the definition and examples of the divalent group represented by ArX2 in the above-mentioned formula (X) in which at least one arylene group and at least one divalent heterocyclic group are directly bonded to each other.

[0347] To achieve a better external quantum efficiency of the light-emitting device according to the present embodiment, Ar2 and Ar4 are preferably arylene groups which may have a substituent.

[0348] The definition and examples of the arylene group represented by Ar2 and Ar4 are the same as the definition and examples of the arylene group represented by ArX1 and ArX3 in the above formula (X).

[0349] The definition and examples of the divalent heterocyclic group represented by Ar2 and Ar4 are the same as the definition and examples of the divalent heterocyclic group represented by ArX1 and ArX3 in the above formula (X).

[0350] The groups represented by Ar2, Ar3, and Ar4 each may have a substituent. Preferable examples of the substituent include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a halogen atom, a monovalent heterocyclic group and a cyano group.

[0351] The definitions and examples of the alkylene group, the cycloalkylene group, the arylene group, and the divalent heterocyclic group represented by KA are each the same as the definitions and examples of the alkylene group, the cycloalkylene group, the arylene group, and the divalent heterocyclic group represented by LA.

[0352] To facilitate the synthesis of the polymer compound of the hole transporting layer, KA is preferably a phenylene group or a methylene group, and these groups each may have a substituent.

[0353] The definitions and examples of the crosslinkable group represented by X' are the same as the definition and examples of the crosslinkable group represented by X described above.

[0354] To achieve better hole transportability of the polymer compound of the hole transporting layer and better crosslinking properties of the polymer compound of the hole transporting layer, the content of the constitutional unit represented by formula (4) is preferably 0.5 to 80 mol%, more preferably 1 to 60 mol%, still more preferably 3 to 40 mol%, and particularly preferably 5 to 20 mol%, based on the total amount of constitutional units contained in the polymer compound of the hole transporting layer.

[0355] Only one constitutional unit represented by formula (4) may be contained or two or more of them may be contained in the polymer compound of the hole transporting layer.

[0356] Examples of constitutional unit represented by formula (3) include constitutional units represented by formulas (3-1) to (3-30), and examples of the constitutional unit represented by formula (4) include constitutional units represented by formulas (4-1) to (4-9). Among these, to achieve better crosslinking properties of the polymer compound of the hole transporting layer, such constitutional unit is preferably a constitutional unit represented by formulas (3-1) to (3-30), more preferably a constitutional unit represented by formulas (3-1) to (3-15), (3-19), (3-20), (3-23), (3-25), or (3-30), still more preferably a constitutional unit represented by formulas (3-1) to (3-13) or (3-30), and particularly preferable a constitutional unit represented by formulas (3-1) to (3-9) or (3-30).









[0357] When the light-emitting device according to the present embodiment comprises an electron transporting layer, the electron transporting material contained in the electron transporting layer is preferably a polymer compound (hereinafter also referred to as "polymer compound of the electron transporting layer") comprising at least one constitutional unit selected from the group consisting of a constitutional unit represented by formula (ET-1) and a constitutional unit represented by formula (ET-2).

(Wherein,

nE1 denotes an integer of 1 or more,

ArE1 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups each may have a substituent other than RE1, and

RE1 represents a group represented by formula (ES-1); when there are a plurality of RE1, they may be the same or different.)



        -RE3-{(QE1)nE3-YE1(ME1)aE1(ZE1)bE1}mE1     (ES-1)

(Wherein,

nE3 denotes an integer of 0 or more, aE1 denotes an integer of 1 or more, bE1 denotes an integer of 0 or more, and mE1 denotes an integer of 1 or more; when there are a plurality of nE3, aE1, and bE1, they may be the same or different at each occurrence; when RE3 is a single bond, mE1 is 1; and aE1 and bE1 are selected so that the charge of the group represented by formula (ES-1) is zero,

RE3 represents a single bond, a hydrocarbon group, a heterocyclic group or O-RE3' (RE3' represents a hydrocarbon group or a heterocyclic group), and these groups each may have a substituent,

QE1 represents an alkylene group, a cycloalkylene group, an arylene group, an oxygen atom, or a sulfur atom, and these groups each may have a substituent; and when there are a plurality of QE1, they may be the same or different,

YE1 represents -CO2-, -SO3-, -SO2-, or PO32-; and when there are a plurality of YE1, they may be the same or different,

ME1 represents an alkali metal cation, an alkali earth metal cation, or an ammonium cation, and the ammonium cation may have a substituent; when there are a plurality of ME1, they may be the same or different, and

ZE1 represents F-, Cl-, Br-, I-, OH-, B(RE4)4-, RE4SO3-, RE4COO-, NO3-, SO42-, HSO4-, PO43-, HPO42-, H2PO4-, BF4-, or PF6-; RE4 represents an alkyl group, a cycloalkyl group, or an aryl group, and these groups each may have a substituent; and when there are a plurality of ZE1, they may be the same or different.)



[0358] nE1 is usually an integer of 1 to 4, and preferably 1 or 2.

[0359] Preferable examples of the aromatic hydrocarbon group or heterocyclic group represented by ArE1 are a group remaining after removing from a 1,4-phenylene group, a 1,3-phenylene group, a 1,2-phenylene group, a 2,6-naphthalenediyl group, a 1,4-naphthalenediyl group, a 2,7-fluorenediyl group, a 3,6-fluorenediyl group, a 2,7-phenanthrenediyl group, or a 2,7-carbazolediyl group, nE1 atoms of hydrogen directly bonded to the atoms constituting the ring, and ArE1 may have a substituent other than RE1.

[0360] Examples of the optional substituent other than RE1 of ArE1 include a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an amino group, a substituted amino group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a cycloalkynyl group, a carboxyl group, and a group represented by formula (ES-3).

        -O-(Cn'H2n'O)nx-Cm'H2m'+1     (ES-3)

(Wherein n', m', and nx each independently denote an integer of 1 or more.)

[0361] nE3 is usually an integer of 0 to 10, preferably an integer of 0 to 8, and more preferably an integer of 0 to 2.

[0362] aE1 is usually an integer of 1 to 10, preferably an integer of 1 to 5, and more preferably 1 or 2.

[0363] bE1 is usually an integer of 0 to 10, preferably an integer of 0 to 4, and more preferably 0 or 1.

[0364] mE1 is usually an integer of 1 to 5, preferably 1 or 2, and more preferably 1.

[0365] When RE3 is -O-RE3', the group represented by formula (ES-1) is a group represented by the following formula.

        -O-RE3'-{(QE1)nE3-YE1(ME1)aE1(ZE1)bE1}mE1



[0366] RE3 is preferably a hydrocarbon group or a heterocyclic group, more preferably an aromatic hydrocarbon group or an aromatic heterocyclic group, and still more preferably an aromatic hydrocarbon group.

[0367] Examples of the optional substituent of RE3 include an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, and a group represented by formula (ES-3), and a group represented by formula (ES-3) is preferable.

[0368] QE1 is preferably an alkylene group, an arylene group, or an oxygen atom, and more preferably an alkylene group or an oxygen atom.

[0369] YE1 is preferably -CO2-, -SO2-, or PO32-, and more preferably -CO2-.

[0370] Examples of the alkali metal cation represented by ME1 include Li+, Na+, K+, Rb+, and Cs+, and K+, Rb+, or Cs+ is preferable and Cs+ is more preferable.

[0371] Examples of the alkali earth metal cation represented by ME1 include Be2+, Mg2+, Ca2+, Sr2+, Ba2+, and Mg2+, Ca2+, Sr2+, and Ba2+ are preferable, and Ba2+ is more preferable.

[0372] Preferable examples of ME1 include an alkali metal cation or an alkali earth metal cation, and an alkali metal cation is more preferable.

[0373] ZE1 is preferably F-, Cl-, Br-, I-, OH-, B(RE4)4-, RE4SO3-, RE4COO-, or NO3-, and more preferably F-, Cl-, Br-, I-, OH-, RE4SO3-, or RE4COO-. RE4 is preferably an alkyl group.

[0374] Examples of the group represented by formula (ES-1) include groups represented by the following formulas.



(Wherein, M+ represents Li+, Na+, K+, Cs+, or N(CH3)4+; and when there are a plurality of M+, they may be the same or different.)

(Wherein,

nE2 denotes an integer of 1 or more,

ArE2 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups each may have a substituent other than RE2, and

RE2 represents a group represented by formula (ES-2); when there are a plurality of RE2, they may be the same or different.)



        -RE5-{(QE2)nE4-YE2(ME2)aE2(ZE2)bE2}mE2     (ES-2)

(Wherein,

nE4 denotes an integer of 0 or more, aE2 denotes an integer of 1 or more, bE2 denotes an integer of 0 or more, and mE2 denotes an integer of 1 or more; when there are a plurality of nE4, aE2, and bE2, they may be the same or different at each occurrence; however, when RE5 is a single bond, mE2 is 1; and aE2 and bE2 are selected so that the charge of the group represented by formula (ES-2) is zero,

RE5 represents a single bond, a hydrocarbon group, a heterocyclic group or O-RE5' (RE5' represents a hydrocarbon group or a heterocyclic group), and these groups each may have a substituent,

QE2 represents an alkylene group, a cycloalkylene group, an arylene group, an oxygen atom, or a sulfur atom, and these groups each may have a substituent; and when there are a plurality of QE2, they may be the same or different,

YE2 represents -C+RE62, -N+RE63, -P+RE63, -S+RE62, or -I+RE62; RE6 represents a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, and these groups each may have a substituent: the plurality of RE6 may be the same or different; and when there are a plurality of YE2, they may be the same or different,

ME2 represents F-, Cl-, Br, I-, OH-, B(RE7)4-, RE7SO3-, RE7COO-, BF4-, SbCl6-, or SbF6-; RE7 represents an alkyl group, a cycloalkyl group, or an aryl group, and these groups each may have a substituent,

when there are a plurality of ME2, they may be the same or different, and

ZE2 represents an alkali metal cation or an alkali earth metal cation; and when there are a plurality of ZE2, they may be the same or different.)



[0375] nE2 is usually an integer of 1 to 4, and preferably 1 or 2.

[0376] Preferable examples of the aromatic hydrocarbon group or heterocyclic group represented by ArE2 are a group remaining after removing from a 1,4-phenylene group, a 1,3-phenylene group, a 1,2-phenylene group, a 2,6-naphthalenediyl group, a 1,4-naphthalenediyl group, a 2,7-fluorenediyl group, a 3,6-fluorenediyl group, a 2,7-phenanthrenediyl group, or a 2,7-carbazolediyl group, nE2 atoms of hydrogen directly bonded to the atoms constituting the ring, and ArE2 may have a substituent other than RE2.

[0377] The examples of the optional substituent other than RE2 of ArE2 are the same as the examples of the optional substituent other than RE1 of ArE1.

[0378] nE4 is usually an integer of 0 to 10, preferably an integer of 0 to 8, and more preferably an integer of 0 to 2.

[0379] aE2 is usually an integer of 1 to 10, preferably an integer of 1 to 5, and more preferably 1 or 2.

[0380] bE2 is usually an integer of 0 to 10, preferably an integer of 0 to 4, and more preferably 0 or 1.

[0381] mE2 is usually an integer of 1 to 5, preferably 1 or 2, and more preferably 1.

[0382] When RE5 is -O-RE5', the group represented by formula (ES-2) is a group represented by the following formula.

        -O-RE5'-{(QE1)nE3-YE1(ME1)aE1(ZE1)bE1}mE1



[0383] RE5 is preferably a hydrocarbon group or a heterocyclic group, more preferably an aromatic hydrocarbon group or an aromatic heterocyclic group, and still more preferably an aromatic hydrocarbon group.

[0384] Examples of the optional substituent of RE5 include an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, and a group represented by formula (ES-3), and a group represented by formula (ES-3) is preferable.

[0385] QE2 is preferably an alkylene group, an arylene group, or an oxygen atom, and more preferably an alkylene group or an oxygen atom.

[0386] YE2 is preferably -C+RE62, -N+RE63, -P+RE63, or -S+RE62, and more preferably -N+RE63. RE6 is preferably a hydrogen atom, an alkyl group, or an aryl group, and more preferably a hydrogen atom or an alkyl group.

[0387] ME2 is preferably F-, Cl-, Br-, I-, B(RE7)4-, RE7SO3-, RE7COO-, BF4-, or SbF6-, and more preferably Br-, I-, B(RE7)4-, RE7COO-, or SbF6-. RE7 is preferably an alkyl group.

[0388] Examples of the alkali metal cation represented by ZE2 include Li+, Na+, K+, Rb+, and Cs+, and Li+, Na+, or K+ is preferable.

[0389] Examples of the alkali earth metal cation represented by ZE2 include Be2+, Mg2+, Ca+, Sr2+, and Ba2+, and Mg2+ or Ca2+ is more preferable.

[0390] ZE2 is preferably an alkali metal cation.

[0391] Examples of the group represented by formula (ES-2) include groups represented by the following formulas.





(Wherein, X- represents F-, Cl-, Br-, I-, B(C6H5)4-, CH3COO-, or CF3SO3-; and when there are a plurality of X-, they may be the same or different.)

[0392] Examples of the constitutional unit represented by formula (ET-1) or (ET-2) include the constitutional units represented by formulas (ET-31) to (ET-38).







[0393] The polymer compound of the electron transporting layer can be synthesized according to the methods described in, for example, Japanese Unexamined Patent Publication No. 2009-239279, Japanese Unexamined Patent Publication No. 2012-033845, Japanese Unexamined Patent Publication No. 2012-216821, Japanese Unexamined Patent Publication No. 2012-216822, and Japanese Unexamined Patent Publication No. 2012-216815.

[Substrate/Electrodes]



[0394] The light-emitting device according to the present embodiment may have a substrate. The substrate in the light-emitting device may be any material that is capable of forming an electrode and that does not chemically change when forming an organic layer (e.g., the light-emitting layer, the hole transporting layer, the hole injecting layer, the electron transporting layer, the electron injecting layer, etc.). The substrate may be made of a material such as glass, plastic, and silicon. In the case of an opaque substrate, it is preferable that the electrode farthest from the substrate be transparent or translucent.

[0395] Examples of the material of the anode include conductive metal oxides and translucent metals. The anode material is preferably indium oxide, zinc oxide, or tin oxide; a conductive compound such as indium tin oxide (ITO) or indium zinc oxide; a complex of silver, palladium, and copper (APC); NESA, gold, platinum, silver, or copper.

[0396] Examples of the material of the cathode include metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, zinc, and indium; alloys of two or more of those metals; alloys of one or more of those metals with one or more of silver, copper, manganese, titanium, cobalt, nickel, tungsten, and tin; and graphite and graphite intercalation compounds. Examples of the alloys include a magnesium-silver alloy, a magnesium-indium alloy, a magnesium-aluminum alloy, an indium-silver alloy, a lithium-aluminum alloy, a lithium-magnesium alloy, a lithium-indium alloy, and a calcium-aluminum alloy, and the like.

[0397] Each of the anode and the cathode may have a stacked structure of two or more layers.

[Light-emitting device Applications]



[0398] To obtain planar light emission using a light-emitting device, a planar anode and a planar cathode may be arranged so as to overlap each other. Examples of methods for obtaining patterned light emission include a method in which a mask having a patterned window is disposed on the surface of a planar light-emitting device, a method in which a layer that is not intended to emit light is formed very thickly so as to substantially prevent light emission, and a method in which the anode or the cathode, or both electrodes, are formed in a pattern shape.

[0399] By forming a pattern by any of these methods and arranging such that several electrodes can be independently switched ON/OFF, a segment type display device capable of displaying numerals, letters, and the like is obtained. To obtain a dot matrix display device, the anodes and the cathodes are formed in a striped shape so as to be orthogonal to each other. Partial color display and multi-color display can be achieved by a method in which a plurality of polymer compounds having different emission colors are used for separate paining or a method in which a color filter or a fluorescence conversion filter are used. A dot matrix display device can be driven passively, or can be driven actively in combination with TFT and the like. These display devices can be used as a display in computers, television sets, mobile terminals, and the like. A planar light-emitting device can be suitably used as a planar light source for a backlight in a liquid crystal display or as a planar illumination light source. When a flexible substrate is used, the light-emitting device can also be used as a curved light source and a curved display.

Examples



[0400] The present invention will now be described in more detail by the following Examples, but the present invention is not limited to these Examples.

[0401] In the Examples, the polystyrene-equivalent number-average molecular weight (Mn) and the polystyrene-equivalent weight-average molecular weight (Mw) of the polymer compounds were determined by any one of the below size-exclusion chromatography (SEC) columns using tetrahydrofuran for the mobile phase. The SEC measurement conditions were as follows.

[0402] The polymer compound to be measured was dissolved at a concentration of about 0.05% by mass in tetrahydrofuran, and 10 µL of the solution was injected into the SEC column. The mobile phase flow rate was 0.6 mL/min. A TSK guard column Super AW-H, a TSKgel Super AWM-H, or a TSKgel Super AW 3000 (all manufactured by Tosoh Corporation) were each connected in series and used for the column. A UV-VIS detector (trade name: UV-8320 GPC, manufactured by Tosoh Corporation) was used as the detector.

[0403] LC-MS was measured by the following method.

[0404] The measurement sample was dissolved in chloroform or tetrahydrofuran so as to have a concentration of about 2 mg/mL, and about 1 µL was injected into an LC-MS (trade name: 1100 LC-MSD, manufactured by Agilent). The LC-MS mobile phase was flowed at a rate of 0.2 mL/min while varying the ratio of acetonitrile and tetrahydrofuran. An L-column 2 ODS (3 µm) (manufactured by the Chemicals Evaluation and Research Institute, inner diameter: 2.1 mm, length: 100 mm, particle diameter 3 µm) was used for the column.

[0405] TLC-MS was measured by the following method.

[0406] The measurement sample was dissolved in a solvent of either toluene, tetrahydrofuran, or chloroform at an arbitrary concentration, and the solution was coated on a TLC plate for DART (trade name: YSK5-100, manufactured by Techno Applications), and then measurement was carried out using TLC-MS (trade name: JMS-T100TD (The AccuTOF TLC), manufactured by JEOL Ltd.). The helium gas temperature during the measurement was adjusted in the range of 200 to 400°C.

[0407] NMR was measured by the following method.

[0408] A measurement sample of 5 to 10 mg was dissolved in about 0.5 mL of deuterated chloroform (CDCl3), heavy tetrahydrofuran, heavy dimethyl sulfoxide, heavy acetone, heavy N,N-dimethylformamide, heavy toluene, heavy methanol, heavy ethanol, heavy 2-propanol, or heavy methylene chloride, and measured using an NMR apparatus (trade name: INOVA 300 or MERCURY 400 VX, manufactured by Agilent).

[0409] As an index of the purity of the compound, the value of the high-performance liquid chromatography (HPLC) area percentage was used. Unless noted otherwise, this value is the value at UV=254 nm in the HPLC apparatus (product name: LC-20A, manufactured by Shimadzu Corporation). At this time, the compound to be measured was dissolved in tetrahydrofuran or chloroform so as to have a concentration of 0.01 to 0.2% by mass, and 1 to 10 µL was injected into the HPLC apparatus in accordance with the concentration. For the HPLC mobile phase, the ratio of acetonitrile/tetrahydrofuran was varied between 100/0 to 0/100 (volume ratio) while flowing at a flow rate of 1.0 mL/min. As the column, a Kaseisorb LC ODS 2000 (manufactured by Tokyo Chemical Industry) or an ODS column having equivalent performance was used. For the detector, a photodiode array detector (trade name: SPD-M20A, manufactured by Shimadzu Corporation) was used.

[0410] In this Example, the maximum peak wavelength of the emission spectrum of the phosphorescent compound was measured at room temperature by a spectrophotometer (FP-6500, manufactured by JASCO Corporation). A xylene solution in which the phosphorescent compound was dissolved in xylene at a concentration of about 0.8 × 10-4 % by mass was used as the sample. For the excitation light, UV light with a wavelength of 325 nm was used.

<Synthesis Example 1>


Synthesis of Compound MC1 (Phosphorescent Compound)



[0411] 



[0412] The atmosphere within a reaction vessel was replaced with argon gas, then the reaction vessel was charged with compound MC1-a (33.7 g) and dichloromethane (400 mL), and placed in an ice bath to cool. The reaction vessel was then charged with a 25% by mass solution of aqueous ammonia (40.8 g), and the reaction vessel was stirred for 1 hour while cooling in an ice bath. Then, the reaction vessel was charged with ion-exchanged water (200 mL) and dichloromethane (150 mL), and the organic layer was extracted. The obtained organic layer was dried over anhydrous magnesium sulfate, then heptane (400 mL) was added, and the dichloromethane was concentrated under reduced pressure to obtain a solution containing a white solid. The obtained solution containing the white solid was filtered, and then the resultant white solid was dried under reduced pressure to obtain compound MC1-b (27.8 g, yield 93%) as a white solid. The HPLC area percentage value of compound MC1-b was 99.3%. The required amount of compound MC1-b was obtained by repeating this operation.

[0413] TLC/MS (DART, positive): m/z = 150 [M+H]+

[0414] The atmosphere within a reaction vessel was replaced with argon gas and then the reaction vessel was charged with compound MC1-b (34.3 g) and dichloromethane (1.38 L). Then, the reaction vessel was charged with a solution of triethyloxonium tetrafluoroborate (1 mol/L, 276 mL) in dichloromethane, and the mixture was stirred at room temperature for 34 hours. Then, the reaction vessel was charged with an aqueous sodium hydrogen carbonate solution (1 mol/L, 352 mL), and the mixture was stirred at room temperature for 30 minutes. After extracting the organic layer of the obtained reaction solution, the resultant organic layer was washed with saturated brine (300 mL) to obtain an organic layer. Heptane (200 mL) was added to the obtained organic layer, and then the dichloromethane was concentrated under reduced pressure to obtain a solution containing a white solid. The obtained solution containing the white solid was filtered, and then the resultant filtrate was concentrated to obtain compound MC1-c (33.6 g, yield 82%) as a yellow oily substance. The HPLC area percentage value of compound MC1-c was 98.0%.

[0415] TLC/MS (DART, positive): m/z = 178 [M+H]+

[0416] The atmosphere within a reaction vessel was replaced with argon gas, then the reaction vessel was charged with compound MC1-c (33.5 g), benzoyl chloride (26.6 g), and chloroform (570 mL). Next, the reaction vessel was charged with triethylamine (26.4 mL), and the mixture was stirred for 66 hours at room temperature. The obtained reaction solution was concentrated under reduced pressure, ion-exchanged water (210 mL) and chloroform (210 mL) were added to the obtained residue, and the organic layer was extracted. The obtained organic layer was washed with saturated brine (150 mL), dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain compound MC1-d (54.2 g, yield 88%) as an orange oily substance. The HPLC area percentage value of compound MC1-d was 86.0%.

[0417] TLC/MS (DART, positive): m/z = 282 [M+H]+

[0418] 1H-NMR (300 MHz, CDCl3-d1): δ (ppm) = 8.01-7.98 (m, 2H), 7.56-7.51 (m, 1H), 7.46-7.41 (m, 2H), 7.19 (s, 2H), 7.03 (s, 1H), 4.48-4.41 (m, 2H), 2.23 (s, 6H), 1.48 (t, 3H).

[0419] The atmosphere within a reaction vessel was replaced with argon gas, then the reaction vessel was charged with compound MC1-e (55.8 g) and toluene (925 mL), and the reaction vessel was placed in an ice bath to cool. Then, the reaction vessel was charged with an aqueous sodium hydroxide solution (1 mol/L, 222 mL), and the mixture was stirred for 30 minutes while cooling in an ice bath. The organic layer of the obtained reaction solution was extracted to obtain a toluene solution as an organic layer.

[0420] The atmosphere of a separately-prepared reaction vessel was replaced with argon gas, then the reaction vessel was charged with compound MC1-d (52.0 g) and chloroform (925 mL), and placed in an ice bath to cool. Then, the reaction vessel was charged with the above-obtained toluene solution, the mixture was stirred for 7 hours while cooling in an ice bath, and then stirred at room temperature for 100 hours. Ion-exchanged water (500 mL) was added to the obtained reaction solution, the organic layer was extracted, and the obtained organic layer was concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (mixed solvent of chloroform and hexane), then recrystallized from a mixed solvent of chloroform and heptane, and then dried under reduced pressure at 50°C to obtain compound MC1-f (17.6 g, yield 22%) as a white solid. The HPLC area percentage value of compound MC1-f was 99.5% or more. The required amount of compound MC1-f was obtained by repeating this operation.

[0421] TLC/MS (DART, positive): m/z = 432 [M+H]+

[0422] 1H-NMR (300 MHz, CD2Cl2-d2): δ (ppm) = 7.84 (s, 2H), 7.56-7.54 (m, 2H), 7.43-7.32 (m, 5H), 7.09 (s, 1H), 2.40 (s, 6H), 1.99 (s, 6H).

[0423] The atmosphere within a reaction vessel was replaced with argon gas, then the reaction vessel was charged with compound MC1-f (17.3 g), cyclopentyl methyl ether (240 mL), and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (98 mg), and the temperature was increased to 50°C. Then, the reaction vessel was charged with a solution of hexyl magnesium bromide (2 mol/L, 40 mL) in diethyl ether, and the mixture was stirred at 50°C for 2 hours. Then, the reaction vessel was charged with an aqueous hydrochloric acid solution (1 mol/L, 80 mL), and the organic layer was extracted. The obtained organic layer was washed twice with ion-exchanged water (100 mL), dried over anhydrous magnesium sulfate, filtered and the resultant filtrate was concentrated under reduced pressure to obtain an oily substance. Toluene and activated carbon were added to the obtained oily substance, and the resultant mixture was stirred at 50°C for 30 minutes. Then, the mixture was filtered through a filter lined with silica gel and Celite, and the resultant filtrate was concentrated under reduced pressure to obtain a solid. The obtained solid was purified by silica gel column chromatography (mixed solvent of hexane and ethyl acetate) and then recrystallized from methanol. Then, the recrystallized product was dried under reduced pressure at 50°C to obtain compound MC1-g (12.1 g, yield 69%) as a white solid. The HPLC area percentage value of compound MC1-g was 99.5% or more.

[0424] TLC/MS (DART, positive): m/z = 438 [M+H]+

[0425] 1H-NMR (300 MHz, CD2Cl2-d2) δ (ppm) = 7.92 (s, 2H), 7.65-7.62 (m, 2H), 7.48-7.35 (m, 3H), 7.15 (s, 1H), 7.09 (s, 2H), 2.70 (t, 2H), 2.46 (s, 6H), 2.03 (s, 6H), 1.77-1.67 (m, 2H), 1.46-1.36 (m, 6H), 1.00-0.95 (m, 3H).

[0426] The atmosphere within a reaction vessel was replaced with argon gas, then the reaction vessel was charged with iridium chloride n-hydrate (2.50 g), compound MC1-g (6.43 g), ion-exchanged water (28 mL), and 2-ethoxyethanol (112 mL), and the mixture was stirred under reflux for 25 hours. Then, toluene was added and the mixture was washed with ion-exchanged water. The organic layer of the obtained washing solution was extracted, and the obtained organic layer was concentrated under reduced pressure to obtain a solid. The obtained solid was purified by silica gel column chromatography (mixed solvent of toluene and methanol) to obtain a solid (4.82 g).

[0427] The atmosphere of a separately-prepared reaction vessel was replaced with argon gas, then the reaction vessel was charged with the solid obtained above (4.81 g), silver trifluoromethanesulfonate (1.43 g), compound MC1-g (4.81 g), and tridecane (1.1 mL), and the mixture was heated and stirred at 150°C for 15 hours. Then, toluene was added, and the mixture was filtered through a filter lined with silica gel and Celite, and the obtained filtrate was washed with ion-exchanged water to obtain an organic layer. The obtained organic layer was concentrated under reduced pressure to obtain a solid. The obtained solid was purified by silica gel column chromatography (mixed solvent of hexane and toluene) and then recrystallized from a mixed solvent of ethyl acetate and ethanol.

[0428] Then, the recrystallized product was dried under reduced pressure at 50°C to give compound MC1 (2.32 g, yield 35%) as a yellow solid. The HPLC area percentage value of compound MC1 was 99.5% or more.

[0429] LC-MS (APCI, positive): m/z = 1502.8 [M+H]+

[0430] 1H-NMR (300 MHz, CD2Cl2-d2) δ (ppm) = 7.96 (s, 6H), 7.07 (s, 6H), 6.91 (s, 3H), 6.60 (t, 3H), 6.51 (t, 3H), 6.41 (d, 3H), 6.29 (d, 3H), 2.70 (t, 6H), 2.09 (s, 18H), 1.85 (s, 9H), 1.76-1.67 (m, 6H), 1.60 (s, 9H), 1.44-1.35 (m, 18H), 1.00-0.95 (m, 9H).

[0431] The maximum peak wavelength of the emission spectrum of compound MC1 was 453 nm.

<Synthesis Example 2> Synthesis of Compound MC2 (Phosphorescent Compound)



[0432] 





[0433] The atmosphere within a reaction vessel was replaced with argon gas, then the reaction vessel was charged with compound MC1 (0.50 g), dichloromethane (25 mL), and N-bromosuccinimide (203 mg), and the mixture was stirred at room temperature for 27.5 hours. Then, the reaction vessel was charge with a 10% by mass solution of aqueous sodium sulfite (4.20 g), then ion-exchanged water (8.40 mL) was added, and the mixture was stirred at room temperature for 30 minutes. An organic layer was extracted from the obtained reaction solution, and the obtained organic layer was filtered with a filter lined with silica gel. Methanol was added to the resultant filtrate to cause a precipitate to form. The obtained precipitate was filtered and vacuum dried at 50°C to obtain compound MC1 TBR (0.55 g, yield 95%) as a yellow solid. The HPLC area percentage value of compound MC1 TBR was 99.5% or more.

[0434] LC-MS (APCI, positive): m/z = 1736.5 [M+H]+

[0435] 1H-NMR (300 MHz, CD2Cl2-d2) δ (ppm) = 7.94 (s, 6H), 7.71 (d, 6H), 6.94 (s, 3H), 6.73-6.70 (m, 3H), 6.29 (d, 3H), 6.25 (d, 3H), 2.72 (t, 6H), 2.10 (s, 18H), 1.84 (s, 9H), 1.77-1.67 (m, 6H), 1.57 (s, 9H), 1.45-1.34 (m, 18H), 0.99-0.94 (m, 9H).

[0436] The atmosphere within a reaction vessel was replaced with argon gas, then the reaction vessel was charged with compound MC1 TBR (0.50 g), compound MC2-a (0.44 g), toluene (30 mL), tris(dibenzylideneacetone)dipalladium(0) (7.9 mg), and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (8.5 mg), and the temperature was increased to 80°C. Then, the reaction vessel was charged with a 20% by mass solution of aqueous tetraethylammonium hydroxide (4.2 mL), and the mixture was stirred under reflux for 6 hours. Then, toluene was added, and the organic layer was extracted. The obtained organic layer was washed with ion-exchanged water, dried over anhydrous magnesium sulfate, filtered through a filter lined with silica gel and Celite, and the obtained filtrate was concentrated under reduced pressure to obtain a solid. The obtained solid was purified by silica gel column chromatography (mixed solvent of hexane and toluene) to give compound MC2 (0.54 g, yield 74%) as a yellow solid.

[0437] The HPLC area percentage value of compound MC2 was 99.5% or more.

[0438] LC-MS (APCI, positive): m/z = 2523.5 [M+H]+

[0439] 1H-NMR (300 MHz, CD2Cl2-d2) δ (ppm) = 8.05 (s (br), 6H), 7.70-7.50 (m, 27H), 7.38 (s (br), 6H), 7.13-7.01 (m, 9H), 6.95 (s, 3H), 6.82 (s (br), 3H), 6.65 (s (br), 3H), 2.25 (t, 6H), 2.11 (s, 18H), 2.02 (s, 9H) 1.71-1.64 (m, 9H), 1.48-1.20 (m, 78H), 0.96-0.86 (m, 9H).

[0440] The maximum peak wavelength of the emission spectrum of compound MC2 was 470 nm.

<Synthesis Example 3> Synthesis of Compound MC3



[0441] 





[0442] The atmosphere within a reaction vessel was replaced with argon gas, then the reaction vessel was charged with compound MC3-a (13.1 g) and tert-butyl methyl ether (110 mL), and the reaction vessel was placed in an ice bath to cool. Then, the reaction vessel was charged with an aqueous sodium hydroxide solution (1 mol/L, 125 mL), and the mixture was stirred for 30 minutes while cooling in an ice bath. The organic layer of the obtained reaction solution was extracted to obtain a tert-butyl methyl ether solution as an organic layer.

[0443] The atmosphere of a separately-prepared reaction vessel was replaced with argon gas, then the reaction vessel was charged with compound MC1-d (11.0 g) and chloroform (220 mL), and placed in an ice bath to cool. Then, the reaction vessel was charged with the above-obtained tert-butyl methyl ether solution, the mixture was stirred for 7 hours while cooling in an ice bath, and then stirred at room temperature for 110 hours. Ion-exchanged water (330 mL) was added to the obtained reaction solution, the organic layer was extracted, and the obtained organic layer was concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (mixed solvent of chloroform and hexane), then, recrystallized from a mixed solvent of chloroform and heptane, and then, dried under reduced pressure at 50°C to obtain compound MC3-b (10.2 g, yield 55%) as a white solid. The HPLC area percentage value of compound MC3-b was 99.5% or more. The required amount of compound MC3-b was obtained by repeating this operation.

[0444] LC-MS (ESI, positive): m/z = 488.2 [M+H]+

[0445] 1H-NMR (CD2Cl2, 300 MHz): δ (ppm) = 7.92 (s, 2H), 7.66-7.62 (m, 2H), 7.52 (s, 2H), 7.52-7.36 (m, 3H), 7.16 (s, 1H), 2.57-2.46 (m, 8H), 1.20 (d, 6H), 0.97 (d, 6H).

[0446] The atmosphere within a reaction vessel was replaced with argon gas, then the reaction vessel was charged with compound MC3-b (10.2 g), compound MC3-c (2.8 g), bis[tri(2-methoxyphenyl)phosphine]palladium(II) dichloride (92.1 mg), toluene (102 mL), and a 20% by mass solution of aqueous tetraethylammonium hydroxide (36.9 g), and the mixture was stirred under reflux for 4 hours. Then, toluene was added, and the organic layer was extracted. The obtained organic layer was washed with ion-exchanged water to obtain an organic layer. The obtained organic layer was dried over anhydrous sodium sulfate, then silica gel (10 g) was added and the mixture was filtered. The obtained filtrate was concentrated under reduced pressure to obtain a solid. The obtained solid was recrystallized from a mixed solvent of heptane and chloroform. Then, the recrystallized product was dried under reduced pressure at 50°C to obtain compound MC3-d (8.55 g, yield 84%) as a white solid. The HPLC area percentage value of compound MC3-d was 99.5% or more.

[0447] LC-MS (ESI, positive): m/z = 486.3 [M+H]+

[0448] 1H-NMR (CD2Cl2, 300 MHz): δ (ppm) = 7.96 (s, 2H), 7.75 (t, 4H), 7.60-7.55 (m, 4H), 7.51-7.41 (m, 4H), 7.17 (s, 1H), 2.63-2.58 (m, 2H), 2.47 (d, 6H), 1.27 (d, 6H), 1.05 (d, 6H).

[0449] The atmosphere within a reaction vessel was replaced with argon gas, then the reaction vessel was charged with iridium chloride n-hydrate (1.96 g), compound MC3-d (5.61 g), ion-exchanged water (20 mL), and digylme (80 mL), and the mixture was heated and stirred at 150°C for 18 hours. Then, toluene was added and the mixture was washed with ion-exchanged water to obtain an organic layer. The obtained organic layer was concentrated under reduced pressure to obtain a solid. The obtained solid was purified by silica gel column chromatography (mixed solvent of toluene and methanol). The purified product was then dried under reduced pressure at 50°C to obtain a solid (5.16 g).

[0450] The atmosphere of a separately-prepared reaction vessel was replaced argon gas, then the reaction vessel was charged with the solid obtained above (4.5 g), silver trifluoromethanesulfonate (1.93 g), compound MC3-d (2.78 g), digylme (4.5 mL), decane (4.5 mL), and 2,6-lutidine (1.1 mL), and the mixture was heated and stirred at 160°C for 31 hours. Then, dichloromethane was added, and the mixture was filtered through a filter lined with Celite. The obtained filtrate was washed with ion-exchanged water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate, then silica gel (18.6 g) was added and the mixture was filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a solid. The obtained solid was purified by silica gel column chromatography (mixed solvent of cyclohexane and dichloromethane) and then recrystallized from a mixed solvent of toluene and acetonitrile. Then, the recrystallized product was dried under reduced pressure at 50°C to give compound MC3-e (1.9 g, yield 24%) as a yellow solid. The HPLC area percentage value of compound MC3-e was 98.9%.

[0451] LC-MS (APCI, positive): m/z = 1646.8 [M+H]+

[0452] 1H-NMR (CD2Cl2, 300 MHz): δ (ppm) = 9.12-7.10 (m, 27H), 7.00 (s, 3H), 6.72 (t, 3H), 6.62-6.33 (m, 9H), 2.74-1.67 (m, 24H), 1.25 (d, 9H), 1.15-1.00 (m, 18H), 0.84 (d, 9H).

[0453] The atmosphere within a reaction vessel was replaced with argon gas, then the reaction vessel was charged with compound MC3-e (0.70 g), dichloromethane (35 mL), and N-bromosuccinimide (825 mg), and the mixture was stirred at room temperature for 40 hours. Then, the reaction vessel was charged with a 10% by mass sodium sulfite aqueous solution (7.7 g), then with ion-exchanged water (15 mL), and the mixture was stirred at room temperature for 30 minutes. The organic layer was extracted from the obtained reaction solution, and the obtained organic layer was filtered with a filter lined with silica gel. Ethanol was added to the obtained filtrate to cause a precipitate to form. The obtained precipitate was filtered and vacuum dried at 50°C to obtain compound MC3-f (0.73 g, yield 91%) as a yellow solid. The HPLC area percentage value of compound MC3-f was 96%.

[0454] LC-MS (APCI, positive): m/z = 1880.5 [M+H]+

[0455] 1H-NMR (CD2Cl2, 300 MHz): δ (ppm) = 8.25-7.83 (m, 6H), 7.76 (d, 6H), 7.76-7.46 (m, 15H), 7.04 (s, 3H), 6.83 (d, 3H), 6.50 (s, 3H), 6.31 (d, 3H), 2.33-1.85 (m, 24H), 1.25 (d, 9H), 1.12-1.07 (m, 18H), 0.84 (d, 9H).

[0456] The atmosphere within a reaction vessel was replaced with argon gas, then the reaction vessel was charged with MC3-f (0.31 g), compound MC2-a (0.31 g), toluene (9.3 mL), and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium( II) (3.5 mg), and the temperature was increased to 90°C. Then, the reaction vessel was charged with a 20% by mass tetraethylammonium hydroxide aqueous solution (2.7 mL), and the mixture was stirred under reflux for 5 hours. Then, toluene was added, and the organic layer was extracted. The obtained organic layer was washed with ion-exchanged water, dried over anhydrous magnesium sulfate, filtered through a filter lined with silica gel, and the obtained filtrate was concentrated under reduced pressure to obtain a solid. The obtained solid was purified by silica gel column chromatography (mixed solvent of cyclohexane and dichloromethane) and then recrystallized from a mixed solvent of dichloromethane and hexane. Then, the recrystallized product was dried under reduced pressure at 50°C to give compound MC3 (0.26 g, yield 60%) as a yellow solid. The HPLC area percentage value of compound MC3 was 99.5% or more.

[0457] LC-MS (APCI, positive): m/z = 2667.5 [M+H]+

[0458] 1H-NMR (CD2Cl2, 300 MHz): δ (ppm) = 8.40-7.32 (m, 60H), 7.15 (d, 3H), 7.05-7.03 (m, 6H), 6.76 (s, 3H), 2.54-2.50 (m, 3H), 2.18-2.13 (m, 18H), 1.38 (s, 54H), 1.31-1.13 (m, 30H), 0.90 (d, 9H).

[0459] The maximum peak wavelength of the emission spectrum of compound MC3 was 469 nm.

(Synthesis Example 4) Synthesis of Compound MC4



[0460] 





[0461] The atmosphere within a reaction vessel was replaced with argon gas, then the reaction vessel was charged with compound MC3-b (17.0 g), cyclopentyl methyl ether (150 mL), and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (172 mg), and the temperature was increased to 50°C. Then, the reaction vessel was charged with a solution of hexyl magnesium bromide (2 mol/L, 35 mL) in diethyl ether, and the mixture was stirred at 50°C for 5 hours. Then, the reaction vessel was charged with an aqueous hydrochloric acid solution (1 mol/L, 35 mL), and the organic layer was extracted. The obtained organic layer was washed twice with ion-exchanged water (85 mL), dried over anhydrous magnesium sulfate, filtered and the resultant filtrate was concentrated under reduced pressure to obtain an oily substance. Toluene and silica gel were added to the obtained oily substance, and the resultant mixture was stirred at room temperature for 30 minutes. Then, the mixture was filtered through a filter lined with Celite, and the resultant filtrate was concentrated under reduced pressure to obtain a solid. The obtained solid was recrystallized from acetonitrile. Then, the recrystallized product was dried under reduced pressure at 50°C to obtain compound MC4-a (13.7 g, yield 80%) as a white solid. The HPLC area percentage value of compound MC4-a was 99.5% or more.

[0462] TLC/MS (DART, positive): m/z = 494 [M+H]+

[0463] 1H-NMR (300 MHz, CD2Cl2-d2) δ (ppm) = 7.92 (s, 2H), 7.67-7.63 (m, 2H), 7.46-7.33 (m, 3H), 7.18 (s, 2H), 7.14 (s, 1H), 2.76 (t, 2H), 2.57-2.46 (m, 8H), 1.77-1.70 (m, 2H), 1.48-1.42 (m, 6H), 1.21-1.19 (m, 6H), 0.98-0.96 (m, 9H).

[0464] The atmosphere within a reaction vessel was replaced with argon gas, then the reaction vessel was charged with iridium chloride trihydrate (2.96 g), compound MC4-a (8.65 g), ion-exchanged water (30 mL), and diglyme (74 mL), and the mixture was stirred under reflux for 18 hours. Then, the mixture was cooled to room temperature, toluene was added, and the mixture was washed with ion-exchanged water. The organic layer of the obtained washing solution was extracted, and the obtained organic layer was concentrated under reduced pressure to obtain a solid. The obtained solid was purified by silica gel column chromatography (mixed solvent of toluene and ethanol) to obtain solid (7.51 g).

[0465] The atmosphere of a separately-prepared reaction vessel was replaced with argon gas, then the reaction vessel was charged with the solid obtained above (7.40 g), silver trifluoromethanesulfonate (3.19 g), compound MC4-a (4.59 g), 2,6-lutidine (1.66 g), and decane (15 mL), and the mixture was heated and stirred at 150°C for 20 hours. Then, the mixture was cooled to room temperature, toluene was added, and the mixture was filtered through a filter lined with silica gel and Celite, and the obtained filtrate was washed with ion-exchanged water to obtain an organic layer. The obtained organic layer was concentrated under reduced pressure to obtain a solid. The obtained solid was purified by silica gel column chromatography (mixed solvent of dichloromethane and cyclohexane) and then recrystallized from a mixed solvent of toluene and methanol. Then, the recrystallized product was dried under reduced pressure at 50°C to give compound MC4-b (1.47 g, yield 14%) as a yellow solid. The HPLC area percentage value of compound MC4-b was 99.4%.

[0466] LC-MS (APCI, positive): m/z = 1671.0 [M+H]+

[0467] 1H-NMR (300 MHz, CD2Cl2-d2) δ (ppm) = 8.03 (br, 6H), 7.17 (s, 6H), 6.96 (s, 3H), 6.66 (t, 3H), 6.51-6.41 (m, 6H), 6.32 (d, 3H), 2.76 (t, 6H), 2.23-1.92 (m, 21H), 1.76-1.69 (m, 6H), 1.58 (s, 3H), 1.53-1.42 (m, 18H), 1.16 (d, 9H), 1.01-0.96 (m, 27H), 0.73 (d, 9H).

[0468] The atmosphere within a reaction vessel was replaced with argon gas, then the reaction vessel was charged with compound MC4-b (1.36 g), dichloromethane (68 mL), and N-bromosuccinimide (1.23 g), and the mixture was stirred at room temperature for 32 hours. Then, the reaction vessel was charged with a 10% by mass solution of aqueous sodium sulfite (8.71 g), then ion-exchanged water (70 mL) was added, and the mixture was stirred at room temperature for 30 minutes. An organic layer was extracted from the obtained reaction solution, and the obtained organic layer was filtered with a filter lined with silica gel. The obtained filtrate was concentrated under reduced pressure to obtain a solid. The obtained solid was dissolved in toluene, and methanol was added to the mixture to cause a precipitate to form. The obtained precipitate was filtered and vacuum dried at 50°C to obtain compound MC4-c (1.47 g, yield 95%) as a yellow solid. The HPLC area percentage value of compound MC4-c was 99.5% or more.

[0469] LC-MS (APCI, positive): m/z = 1903.7 [M+H]+

[0470] 1H-NMR (300 MHz, CD2Cl2-d2) δ (ppm) = 8.00 (br, 6H), 7.20 (s, 6H), 6.99 (s, 3H), 6.67 (d, 3H), 6.36 (d, 3H), 6.25 (d, 3H), 2.78 (t, 6H), 2.06-1.69 (m, 30H), 1.46-1.41 (m, 18H), 1.16 (d, 9H), 1.03-0.94 (m, 27H), 0.74 (d, 9H).

[0471] The atmosphere within a reaction vessel was replaced with argon gas, then the reaction vessel was charged with compound MC4-c (1.30 g), compound MC4-d (0.44 g), toluene (65 mL), and (di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (16 mg), and the temperature was increased to 80°C. Then, the reaction vessel was charged with a 20% by mass tetrabutylammonium hydroxide aqueous solution (23 mL), and the mixture was stirred under reflux for 36 hours. Then, the mixture was cooled to room temperature, toluene was added, and the organic layer was extracted. The obtained organic layer was washed with ion-exchanged water, dried over anhydrous magnesium sulfate, filtered through a filter lined with silica gel and Celite, and the obtained filtrate was concentrated under reduced pressure to obtain a solid. The obtained solid was purified by silica gel column chromatography (mixed solvent of dichloromethane and cyclohexane) and then recrystallized from a mixed solvent of ethyl acetate and acetonitrile. Then, the recrystallized product was dried under reduced pressure at 50°C to give compound MC4 (0.93 g, yield 72%) as a yellow solid. The HPLC area percentage value of compound MC4 was 99.5% or more.

[0472] LC-MS (APCI, positive): m/z = 2067.3 [M+H]+

[0473] 1H-NMR (300 MHz, CD2Cl2-d2) δ (ppm) = 8.04 (br, 6H), 7.30-7.26 (m, 12H), 7.06-6.98 (m, 12H), 6.70 (s, 3H), 6.54 (d, 3H), 2.82 (t, 6H), 2.32-1.78 (m, 27H), 1.59-1.42 (m, 21H), 1.34 (s, 27H), 1.20 (d, 9H), 1.10 (d, 9H), 1.04-0.98 (m, 18H), 0.73 (d, 9H).

[0474] The maximum peak wavelength of the emission spectrum of compound MC4 was 469 nm.

<Synthesis Example 5> Synthesis of Compound MC5



[0475] 





[0476] Compound MC5 was synthesized according to the methods described in Japanese Unexamined Patent Publication No. 2013-147551.

[0477] The maximum peak wavelength of the emission spectrum of compound MC5 was 475 nm.

<Preparation of Compounds G1, G2, G3, G4, G5 and G6>



[0478] Compound G1 (COM-1) was synthesized according to the methods described in Japanese Unexamined Patent Publication No. 2013-237789.

[0479] Compounds G2 and G5 were synthesized according to the methods described in International Publication No. 2004/026886.

[0480] Compound G3 was synthesized according to the methods described in International Publication No. 2009/131255.

[0481] Compound G4 (Ir(ppy)3) was purchased from Luminescence Technology Corp.

[0482] Compound G6 was synthesized according to the methods described in Japanese Unexamined Patent Publication No. 2014/224101 and International Publication No. 2009/131255.



[0483] The maximum peak wavelength of the emission spectrum of compound G1 was 508 nm.

[0484] The maximum peak wavelength of the emission spectrum of compound G2 was 518 nm.

[0485] The maximum peak wavelength of the emission spectrum of compound G3 was 514 nm.

[0486] The maximum peak wavelength of the emission spectrum of compound G4 was 510 nm.

[0487] The maximum peak wavelength of the emission spectrum of compound G5 was 517 nm.

[0488] The maximum peak wavelength of the emission spectrum of compound G6 was 544 nm.

<Preparation of Compounds R1, R2, R3, R4, R5 and R6>



[0489] Compound R1 was synthesized according to the methods described in International Publication No. 2002/44189.

[0490] Compound R2 (COM-5) was synthesized according to the methods described in Japanese Unexamined Patent Publication No. 2006-188673.

[0491] Compound R3 (COM-2) was purchased from American Dye Source.

[0492] Compound R4 was purchased from Luminescence Technology Corp.

[0493] Compound R5 (COM-3) was synthesized according to the methods described in Japanese Unexamined Patent Publication No. 2006-188673.

[0494] Compound R6 was synthesized according to the method described in Japanese Unexamined Patent Publication No. 2008-179617.





[0495] The maximum peak wavelength of the emission spectrum of compound R1 was 617 nm.

[0496] The maximum peak wavelength of the emission spectrum of compound R2 was 619 nm.

[0497] The maximum peak wavelength of the emission spectrum of compound R3 was 618 nm.

[0498] The maximum peak wavelength of the emission spectrum of compound R4 was 614 nm.

[0499] The maximum peak wavelength of the emission spectrum of compound R5 was 626 nm.

[0500] The maximum peak wavelength of the emission spectrum of compound R6 was 595 nm.

<Synthesis Example 6> Synthesis of Polymer Compound HTL-1



[0501] Polymer compound HTL-1 was synthesized by the following steps 1 to 4.

[0502] (Step 1) The atmosphere within a reaction vessel was replaced with inert gas, then the reaction vessel was charged with compound CM7 (0.917 g) described in International Publication No. 2005/049546, compound CM8 (0.0496 g) described in International Publication No. 2013/146806, compound CM10 (0.923 g) synthesized according to the method described in International Publication No. 2015/145871, dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.76 mg), and toluene (34 ml), and the mixture was heated to 105°C.



[0503] (Step 2) A 20% by mass solution of aqueous tetraethylammonium hydroxide (6.7 mL) was added dropwise to the reaction solution, and the mixture was refluxed for 6 hours.

[0504] (Step 3) After the reaction, phenylboronic acid (48.8 mg), dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.88 mg) were added, and the mixture was refluxed for 14.5 hours.

[0505] (Step 4) Then, an aqueous sodium diethyldithiocarbamate solution was added, and the mixture was stirred at 80°C for 2 hours. The reaction solution was cooled, then washed twice with water, twice with 3% by mass aqueous acetic acid solution, and twice with water, and the resultant solution was dropped into methanol, which caused a precipitate to form. The resultant precipitate was dissolved in toluene and purified by passing through an alumina column and a silica gel column in that order. The obtained solution was dropped into methanol, and the mixture was stirred, which caused a precipitate to form. The obtained precipitate was collected by filtration and dried to obtain 1.23 g of the polymer compound HTL-1.

[0506] The polystyrene-equivalent number-average molecular weight of the polymer compound HTL-1 was 2.3 × 104, and the polystyrene-equivalent weight-average molecular weight was 1.2 × 105.

[0507] The polymer compound HTL-1 was a copolymer having, based on the theoretical values obtained from the amounts of the charged raw materials, a molar ratio among the constitutional unit derived from compound CM7, the constitutional unit derived from compound CM8, and the constitutional unit derived from compound CM10 of 50:5:45.

<Synthesis Example 7> Synthesis of Polymer Compound ETL-1 (Synthesis of Polymer Compound ETL-1a)



[0508] The polymer compound ETL-1a was synthesized according to the synthesis methods described in Japanese Unexamined Patent Publication No. 2012-33845 using the compound ET1-1 synthesized according to the methods described in Japanese Unexamined Patent Publication No. 2012-33845 and the compound M4 synthesized according to the synthesis methods described in Japanese Unexamined Patent Publication No. 2012-33845.



[0509] The Mn of the polymer compound ETL-1a was 5.2 × 104.

[0510] The polymer compound ETL-1a was a copolymer having, based on the theoretical values obtained from the amounts of the charged raw materials, a molar ratio among the constitutional unit derived from compound ET1-1 and the constitutional unit derived from compound M4 of 50:50.

(Synthesis of Polymer Compound ETL-1)



[0511] The atmosphere within a reaction vessel was replaced with inert gas, then the reaction vessel was charged with polymer compound ETL-1a (200 mg), tetrahydrofuran (20 mL), and ethanol (20 mL), and the mixture was heated to 55°C. Then, cesium hydroxide (200 mg) dissolved in water (2 mL) was added, and the mixture was stirred at 55°C for 6 hours. Then, the mixture was cooled to room temperature, and concentrated under reduced pressure to obtain a solid. The obtained solid was washed with water and then dried under reduced pressure to obtain polymer compound ETL-1 (150 mg, pale yellow solid). From the NMR spectrum of the obtained polymer compound ETL-1, it was confirmed that the signal derived from the ethyl group at the ethyl ester site of the polymer compound ETL-1a had completely disappeared.


<Example D1> Fabrication and Evaluation of Light-Emitting Device D1


(Fabrication of Light-Emitting Device D1)


[Formation of Anode and Hole Injection Layer]



[0512] An ITO film with a thickness of 45 nm was attached to a glass substrate by a sputtering method to form an anode. On the anode, a polythiophene-sulfonic acid type hole injection material AQ-1200 (manufactured by Plextronics) was spin-coated to form a film with a thickness of 35 nm, and the film was heated on a hot plate at 170°C for 15 minutes under an air atmosphere to form a hole injection layer.

[Formation of Hole Transporting Layer]



[0513] A polymer compound HTL-1 was dissolved at a concentration of 0.7% by mass in xylene. The resultant xylene solution was spin-coated on the hole injection layer to form a film with a thickness of 20 nm, and the film was heated on a hot plate at 180°C for 60 minutes under a nitrogen gas atmosphere to form a hole transporting layer.

[Formation of Light-Emitting Layer]



[0514] Low molecular weight compound HM-1 (compound represented by formula (H-113)) (manufactured by Luminescence Technology Corp), compound MC1, and compound R1 (low molecular weight compound HM-1/compound MC1/compound R1=74% by mass/25% by mass/1% by mass) were dissolved in toluene at a concentration of 2.0% by mass. The resultant toluene solution was spin-coated on the hole transporting layer to form a film with a thickness of 75 nm, and the film was heated at 130°C for 10 minutes under a nitrogen gas atmosphere to form a light-emitting layer.


[Formation of Electron Transporting Layer]



[0515] A polymer compound ETL-1 was dissolved at a concentration of 0.25% by mass in 2,2,3,3,4,4,5,5-octafluoro-1-pentanol. The resultant 2,2,3,3,4,4,5,5-octafluoro-1-pentanol solution was spin-coated on the light-emitting layer to form a film with a thickness of 10 nm, and the film was heated at 130°C for 10 minutes under a nitrogen gas atmosphere to form an electron transporting layer.

[Formation of Cathode]



[0516] The cathode was formed by placing the substrate on which the electron transporting layer had been formed in a vapor deposition machine, then reducing the pressure to 1.0 × 10-4 Pa or less, followed by vapor-depositing sodium fluoride to a thickness of about 4 nm on the electron transporting layer, and then vapor-deposited aluminum to a thickness of about 80 nm on the sodium fluoride layer.

[0517] After the cathode had been formed, sealing was performed using a glass substrate to fabricate a light-emitting device D1.

(Evaluation of Light-Emitting Device D1)



[0518] EL emission was observed by applying a voltage to the light-emitting device D1. The external quantum efficiency (hereinafter, referred to as "EQE") at 500 cd/m2 was 8.76 [%], and the CIE chromaticity coordinate (x, y) was (0.594, 0.308). The results are shown in Table 2.

[0519] After setting the current value so that the initial luminance of the light-emitting device CD1 was 1000 cd/m2, the light-emitting device CD1 was driven at a constant current, and the time until the luminance reached 75% of the initial luminance (hereinafter, referred to as "LT75") was measured to be 20.8 hours.

<Comparative Example CD1> Fabrication and Evaluation of Light-Emitting Device CD1



[0520] A light-emitting device CD1 was fabricated in the same manner as in Example D1, except that a low molecular weight compound HM-1, compound MC1, and compound R3 (low molecular weight compound HM-1/compound MC1/compound R3= 74% by mass/25% by mass/1% by mass) was used in place of a low molecular weight compound HM-1, compound MC1, and compound R1 (low molecular weight compound HM-1/compound MC1/compound R1= 74% by mass/25% by mass/1% by mass) in the (Formation of Light-Emitting Layer) of Example D1.

[0521] EL emission was observed by applying a voltage to the light-emitting device CD1. The EQE at 500 cd/m2 was 6.26 [%], and the CIE chromaticity coordinate (x, y) was (0.292, 0.252). The results are shown in Table 2. Further, the LT75 at 1000 cd/m2 was 5.3 hours.

<Comparative Example CD2> Fabrication and Evaluation of Light-Emitting Device CD2



[0522] A light-emitting device CD2 was fabricated in the same manner as in Example D1, except that a low molecular weight compound HM-1, compound MC1, and compound R4 (low molecular weight compound HM-1/compound MC1/compound R4= 74% by mass/25% by mass/1% by mass) was used in place of a low molecular weight compound HM-1, compound MC1, and compound R1 (low molecular weight compound HM-1/compound MC1/compound R1= 74% by mass/25% by mass/1 % by mass) in the (Formation of Light-Emitting Layer) of Example D1.

[0523] EL emission was observed by applying a voltage to the light-emitting device CD2. The EQE at 500 cd/m2 was 4.67 [%], and the CIE chromaticity coordinate (x, y) was (0.460, 0.283). The results are shown in Table 2. Further, the LT75 at 1000 cd/m2 was 2.9 hours.
[Table 2]
 Light-Emitting DeviceLight-Emitting LayerEQE [%]CIE Chromaticity Coordinate (x, y)
CompositionComposition Ratio (% by mass)(500 cd/m2)(500 cd/m2)
Example D1 D1 HM-1/MC1/R1 74/25/1 8.76 (0.594, 0.308)
Comparative Example CD1 CD1 HM-1/MC1/R3 74/25/1 6.26 (0.292, 0.252)
Comparative Example CD2 CD2 HM-1/MC1/R4 74/25/1 4.67 (0.460, 0.283)

<Example D2> Fabrication and Evaluation of Light-Emitting Device D2



[0524] A light-emitting device D2 was fabricated in the same manner as in Example D1, except that a low molecular weight compound HM-1, compound MC1, compound G1, and compound R4 (low molecular weight compound HM-1/compound MC1/compound G1/compound R4= 73.9% by mass/25% by mass/1% by mass/0.1% by mass) was used in place of a low molecular weight compound HM-1, compound MC1, and compound R1 (low molecular weight compound HM-1/compound MC1/compound R1= 74% by mass/25% by mass/1% by mass) in the (Formation of Light-Emitting Layer) of Example D1.

[0525] EL emission was observed by applying a voltage to the light-emitting device D2. The EQE at 500 cd/m2 was 9.32 [%], and the CIE chromaticity coordinate (x, y) was (0.266, 0.550). The results are shown in Table 3.

<Example D3> Fabrication and Evaluation of Light-Emitting Device D3



[0526] A light-emitting device D3 was fabricated in the same manner as in Example D1, except that a low molecular weight compound HM-1, compound MC1, compound G1, and compound R1 (low molecular weight compound HM-1/compound MC1/compound G1/compound R1= 73.9% by mass/25% by mass/1% by mass/0.1% by mass) was used in place of a low molecular weight compound HM-1, compound MC1, and compound R1 (low molecular weight compound HM-1/compound MC1/compound R1= 74% by mass/25% by mass/1% by mass) in the (Formation of Light-Emitting Layer) of Example D1.

[0527] EL emission was observed by applying a voltage to the light-emitting device D3. The EQE at 500 cd/m2 was 10.6 [%], and the CIE chromaticity coordinate (x, y) was (0.329, 0.510). The results are shown in Table 3. Further, the LT75 at 1000 cd/m2 was 30.8 hours.

<Example D4> Fabrication and Evaluation of Light-Emitting Device D4



[0528] A light-emitting device D4 was fabricated in the same manner as in Example D1, except that a low molecular weight compound HM-1, compound MC2, compound G1, and compound R2 (low molecular weight compound HM-1/compound MC2/compound G1/compound R2= 73.9% by mass/25% by mass/1% by mass/0.1% by mass) was used in place of "a low molecular weight compound HM-1, compound MC1, and compound R1 (low molecular weight compound HM-1/compound MC1/compound R1= 74% by mass/25% by mass/1% by mass) in the (Formation of Light-Emitting Layer) of Example D1.

[0529] EL emission was observed by applying a voltage to the light-emitting device D4. The EQE at 500 cd/m2 was 13.0 [%], and the CIE chromaticity coordinate (x, y) was (0.279, 0.534). The results are shown in Table 3.

<Example D5> Fabrication and Evaluation of Light-Emitting Device D5



[0530] A light-emitting device D5 was fabricated in the same manner as in Example D1, except that a low molecular weight compound HM-1, compound MC2, compound G1, and compound R5 (low molecular weight compound HM-1/compound MC2/compound G1/compound R5 = 73.9% by mass/25% by mass/1% by mass/0.1% by mass) was used in place of a low molecular weight compound HM-1, compound MC1, and compound R1 (low molecular weight compound HM-1/compound MC1/compound R1 = 74% by mass/25% by mass/1% by mass) in the (Formation of Light-Emitting Layer) of Example D1.

[0531] EL emission was observed by applying a voltage to the light-emitting device D5. The EQE at 500 cd/m2 was 12.1 [%], and the CIE chromaticity coordinate (x, y) was (0.297, 0.522). The results are shown in Table 3. Further, the LT75 at 1000 cd/m2 was 33.4 hours.

<Example D6> Fabrication and Evaluation of Light-Emitting Device D6



[0532] A light-emitting device D6 was fabricated in the same manner as in Example D1, except that a low molecular weight compound HM-1, compound MC1, compound G2, and compound R2 (low molecular weight compound HM-1/compound MC1/compound G2/compound R2= 73.9% by mass/25% by mass/1% by mass/0.1% by mass) was used in place of a low molecular weight compound HM-1, compound MC1, and compound R1 (low molecular weight compound HM-1/compound MC1/compound R1= 74% by mass/25% by mass/1% by mass) in the (Formation of Light-Emitting Layer) of Example D1.

[0533] EL emission was observed by applying a voltage to the light-emitting device D6. The EQE at 500 cd/m2 was 9.03 [%], and the CIE chromaticity coordinate (x, y) was (0.316, 0.534). The results are shown in Table 3.

<Example D7> Fabrication and Evaluation of Light-Emitting Device D7



[0534] A light-emitting device D7 was fabricated in the same manner as in Example D1, except that a low molecular weight compound HM-1, compound MC2, compound G2, and compound R2 (low molecular weight compound HM-1/compound MC2/compound G2/compound R2= 73.9% by mass/25% by mass/1% by mass/0.1% by mass) was used in place of a low molecular weight compound HM-1, compound MC1, and compound R1 (low molecular weight compound HM-1/compound MC1/compound R1= 74% by mass/25% by mass/1% by mass) in the (Formation of Light-Emitting Layer) of Example D1.

[0535] EL emission was observed by applying a voltage to the light-emitting device D7. The EQE at 500 cd/m2 was 11.3 [%], and the CIE chromaticity coordinate (x, y) was (0.304, 0.537). The results are shown in Table 3.

<Example D8> Fabrication and Evaluation of Light-Emitting Device D8



[0536] A light-emitting device D8 was fabricated in the same manner as in Example D1, except that a low molecular weight compound HM-1, compound MC1, compound G2, and compound R6 (low molecular weight compound HM-1/compound MC1/compound G2/compound R6= 73.9% by mass/25% by mass/1% by mass/0.1% by mass) was used in place of a low molecular weight compound HM-1, compound MC1, and compound R1 (low molecular weight compound HM-1/compound MC1/compound R1= 74% by mass/25% by mass/1% by mass) in the (Formation of Light-Emitting Layer) of Example D1.

[0537] EL emission was observed by applying a voltage to the light-emitting device D8. The EQE at 500 cd/m2 was 9.39 [%], and the CIE chromaticity coordinate (x, y) was (0.398, 0.498). The results are shown in Table 3. Further, the LT75 at 1000 cd/m2 was 45.5 hours.

<Example D9> Fabrication and Evaluation of Light-Emitting Device D9



[0538] A light-emitting device D9 was fabricated in the same manner as in Example D1, except that a low molecular weight compound HM-1, compound MC2, compound G2, and compound R6 (low molecular weight compound HM-1/compound MC2/compound G2/compound R6= 73.9% by mass/25% by mass/1% by mass/0.1% by mass) was used in place of a low molecular weight compound HM-1, compound MC1, and compound R1 (low molecular weight compound HM-1/compound MC1/compound R1= 74% by mass/25% by mass/1% by mass) in the (Formation of Light-Emitting Layer) of Example D1.

[0539] EL emission was observed by applying a voltage to the light-emitting device D9. The EQE at 500 cd/m2 was 11.5 [%], and the CIE chromaticity coordinate (x, y) was (0.384, 0.506). The results are shown in Table 3.

<Example D10> Fabrication and Evaluation of Light-Emitting Device D10



[0540] A light-emitting device D10 was fabricated in the same manner as in Example D1, except that a low molecular weight compound HM-1, compound MC2, compound G3, and compound R2 (low molecular weight compound HM-1/compound MC2/compound G3/compound R2= 73.9% by mass/25% by mass/1% by mass/0.1% by mass) was used in place of a low molecular weight compound HM-1, compound MC1, and compound R1 (low molecular weight compound HM-1/compound MC1/compound R1= 74% by mass/25% by mass/1% by mass) in the (Formation of Light-Emitting Layer) of Example D1.

[0541] EL emission was observed by applying a voltage to the light-emitting device D10. The EQE at 500 cd/m2 was 9.74 [%], and the CIE chromaticity coordinate (x, y) was (0.274, 0.472). The results are shown in Table 3.

<Comparative Example CD3> Fabrication and Evaluation of Light-Emitting Device CD3



[0542] A light-emitting device CD3 was fabricated in the same manner as in Example D1, except that a low molecular weight compound HM-1, compound MC1, compound G4, and compound R4 (low molecular weight compound HM-1/compound MC1/compound G4/compound R4= 73.9% by mass/25% by mass/1% by mass/0.1% by mass) was used in place of a low molecular weight compound HM-1, compound MC1, and compound R1 (low molecular weight compound HM-1/compound MC1/compound R1= 74% by mass/25% by mass/1% by mass) in the (Formation of Light-Emitting Layer) of Example D1.

[0543] EL emission was observed by applying a voltage to the light-emitting device CD3. The EQE at 500 cd/m2 was 8.69 [%], and the CIE chromaticity coordinate (x, y) was (0.275, 0.540). The results are shown in Table 3. Further, the LT75 at 1000 cd/m2 was 19.5 hours.

<Comparative Example CD4> Fabrication and Evaluation of Light-Emitting Device CD4



[0544] A light-emitting device CD4 was fabricated in the same manner as in Example D1, except that a low molecular weight compound HM-1, compound MC1, compound G4, and compound R3 (low molecular weight compound HM-1/compound MC1/compound G4/compound R3= 73.9% by mass/25% by mass/1% by mass/0.1% by mass) was used in place of a low molecular weight compound HM-1, compound MC1, and compound R1 (low molecular weight compound HM-1/compound MC1/compound R1= 74% by mass/25% by mass/1% by mass in the (Formation of Light-Emitting Layer) of Example D1).

[0545] EL emission was observed by applying a voltage to the light-emitting device CD4. The EQE at 500 cd/m2 was 8.41 [%], and the CIE chromaticity coordinate (x, y) was (0.323, 0.500). The results are shown in Table 3. Further, the LT75 at 1000 cd/m2 was 25.3 hours.
[Table 3]
 Light-Emitting DeviceLight-Emitting LayerEQE [%]CIE Chromaticity Coordinate (x, y)
CompositionComposition Ratio (% by mass)(500 cd/m2)(500 cd/m2)
Example D2 D2 HM-1/MC1/G1/R4 73.9/25/1/0.1 9.32 (0.266, 0.550)
Example D3 D3 HM-1/MC1/G1/R1 73.9/25/1/0.1 10.6 (0.329, 0.510)
Example D4 D4 HM-1/MC2/G1/R2 73.9/25/1/0.1 13.0 (0.279, 0.534)
Example D5 D5 HM-1/MC2/G1/R5 73.9/25/1/0.1 12.1 (0.297, 0.522)
Example D6 D6 HM-1/MC1/G2/R2 73.9/25/1/0.1 9.03 (0.316, 0.534)
Example D7 D7 HM-1/MC2/G2/R2 73.9/25/1/0.1 11.3 (0.304, 0.537)
Example D8 D8 HM-1/MC1/G2/R6 73.9/25/1/0.1 9.39 (0.398, 0.498)
Example D9 D9 HM-1/MC2/G2/R6 73.9/25/1/0.1 11.5 (0.384, 0.506)
Example D10 D10 HM-1/MC2/G3/R2 73.9/25/1/0.1 9.74 (0.274, 0.472)
Comparative Example CD3 CD3 HM-1/MC1/G4/R4 73.9/25/1/0.1 8.69 (0.275, 0.540)
Comparative Example CD4 CD4 HM-1/MC1/G4/R3 73.9/25/1/0.1 8.41 (0.323, 0.500)

<Example D11> Fabrication and Evaluation of Light-Emitting Device D11



[0546] A light-emitting device D11 was fabricated in the same manner as in Example D1, except that a low molecular weight compound HM-1, compound MC3, compound G5, and compound R2 (low molecular weight compound HM-1/compound MC3/compound G5/compound R2= 73.9% by mass/25% by mass/1% by mass/0.1% by mass) was used in place of a low molecular weight compound HM-1, compound MC1, and compound R1 (low molecular weight compound HM-1/compound MC1/compound R1= 74% by mass/25% by mass/1% by mass) in the (Formation of Light-Emitting Layer) of Example D1.

[0547] EL emission was observed by applying a voltage to the light-emitting device D11. The EQE at 100 cd/m2 was 8.89 [%], and the CIE chromaticity coordinate (x, y) was (0.416, 0.475). The results are shown in Table 4.

[0548] After setting the current value so that the initial luminance of the light-emitting device D11 was 1000 cd/m2, the light-emitting device D11 was driven at a constant current, and the time until the luminance reached 90% of the initial luminance (hereinafter, referred to as "LT90") was measured to be 7.32 hours.

<Comparative Example CD5> Fabrication and Evaluation of Light-Emitting Device CD5



[0549] A light-emitting device CD5 was fabricated in the same manner as in Example D1, except that a low molecular weight compound HM-1, compound MC5, compound G5, and compound R2 (low molecular weight compound HM-1/compound MC5/compound G5/compound R2= 73.9% by mass/25% by mass/1% by mass/0.1% by mass) was used in place of a low molecular weight compound HM-1, compound MC1, and compound R1 (low molecular weight compound HM-1/compound MC1/compound R1= 74% by mass/25% by mass/1% by mass) in the (Formation of Light-Emitting Layer) of Example D1.

[0550] EL emission was observed by applying a voltage to the light-emitting device CD5. The EQE at 100 cd/m2 was 8.53 [%], and the CIE chromaticity coordinate (x, y) was (0.392, 0.435). The results are shown in Table 4. Further, the LT90 at 1000 cd/m2 was 0.961 hours.
[Table 4]
 Light-Emitting DeviceLight-Emitting LayerEQE [%]CIE Chromaticity Coordinate (x, y)
CompositionComposition Ratio (% by mass)(100 cd/m2)(100 cd/m2)
Example D11 D11 HM-1/MC3/G5/R2 73.9/25/1/0.1 8.89 (0.416, 0.475)
Comparative Example CD5 CD5 HM-1/MC5/G5/R2 73.9/25/1/0.1 8.53 (0.392, 0.435)

<Example D12> Fabrication and Evaluation of Light-Emitting Device D12



[0551] A light-emitting device D12 was fabricated in the same manner as in Example D1, except that a low molecular weight compound HM-1, compound MC3, compound G6, and compound R2 (low molecular weight compound HM-1/compound MC3/compound G6/compound R2= 73.9% by mass/25% by mass/1% by mass/0.1% by mass) was used in place of a low molecular weight compound HM-1, compound MC1, and compound R1 (low molecular weight compound HM-1/compound MC1/compound R1= 74% by mass/25% by mass/1% by mass) in the (Formation of Light-Emitting Layer) of Example D1.

[0552] EL emission was observed by applying a voltage to the light-emitting device D12. The EQE at 10 kcd/m2 was 8.46 [%], and the CIE chromaticity coordinate (x, y) was (0.393, 0.448). The results are shown in Table 5. Further, the LT90 at 1000 cd/m2 was 2.98 hours.

<Example D13> Fabrication and Evaluation of Light-Emitting Device D13



[0553] A light-emitting device D13 was fabricated in the same manner as in Example D1, except that a low molecular weight compound HM-1, compound MC4, compound G1, and compound R5 (low molecular weight compound HM-1/compound MC4/compound G1/compound R5= 73.9% by mass/25% by mass/1% by mass/0.1% by mass) was used in place of a low molecular weight compound HM-1, compound MC1, and compound R1 (low molecular weight compound HM-1/compound MC1/compound R1= 74% by mass/25% by mass/1% by mass) in the (Formation of Light-Emitting Layer) of Example D1.

[0554] EL emission was observed by applying a voltage to the light-emitting device D13. The EQE at 10 kcd/m2 was 9.35 [%], and the CIE chromaticity coordinate (x, y) was (0.307, 0.494). The results are shown in Table 5. Further, the LT90 at 1000 cd/m2 was 2.24 hours.

<Example D14> Fabrication and Evaluation of Light-Emitting Device D14



[0555] A light-emitting device D14 was fabricated in the same manner as in Example D1, except that a low molecular weight compound HM-1, compound MC3, compound G3, and compound R2 (low molecular weight compound HM-1/compound MC3/compound G3/compound R2= 73.9% by mass/25% by mass/1% by mass/0.1% by mass) was used in place of a low molecular weight compound HM-1, compound MC1, and compound R1 (low molecular weight compound HM-1/compound MC1/compound R1= 74% by mass/25% by mass/1% by mass) in the (Formation of Light-Emitting Layer) of Example D1.

[0556] EL emission was observed by applying a voltage to the light-emitting device D14. The EQE at 10 kcd/m2 was 7.48 [%], and the CIE chromaticity coordinate (x, y) was (0.282, 0.484). The results are shown in Table 5. Further, the LT90 at 1000 cd/m2 was 4.48 hours.

<Example D15> Fabrication and Evaluation of Light-Emitting Device D15



[0557] A light-emitting device D15 was fabricated in the same manner as in Example D1, except that a low molecular weight compound HM-1, compound MC4, compound G3, and compound R2 (low molecular weight compound HM-1/compound MC4/compound G3/compound R2= 73.9% by mass/25% by mass/1% by mass/0.1% by mass) was used in place of a low molecular weight compound HM-1, compound MC1, and compound R1 (low molecular weight compound HM-1/compound MC1/compound R1= 74% by mass/25% by mass/1% by mass) in the (Formation of Light-Emitting Layer) of Example D1.

[0558] EL emission was observed by applying a voltage to the light-emitting device D15. The EQE at 10 kcd/m2 was 8.59 [%], and the CIE chromaticity coordinate (x, y) was (0.275, 0.461). The results are shown in Table 5.

<Example D16> Fabrication and Evaluation of Light-Emitting Device D16



[0559] A light-emitting device D16 was fabricated in the same manner as in Example D1, except that a low molecular weight compound HM-1, compound MC4, compound G3, and compound R6 (low molecular weight compound HM-1/compound MC4/compound G3/compound R6= 73.9% by mass/25% by mass/1% by mass/0.1% by mass) was used in place of a low molecular weight compound HM-1, compound MC1, and compound R1 (low molecular weight compound HM-1/compound MC1/compound R1= 74% by mass/25% by mass/1% by mass) in the (Formation of Light-Emitting Layer) of Example D1.

[0560] EL emission was observed by applying a voltage to the light-emitting device D16. The EQE at 10 kcd/m2 was 8.07 [%], and the CIE chromaticity coordinate (x, y) was (0.387, 0.453). The results are shown in Table 5.

<Example D17> Fabrication and Evaluation of Light-Emitting Device D17



[0561] A light-emitting device D17 was fabricated in the same manner as in Example D1, except that a low molecular weight compound HM-1, compound MC4, compound G3, and compound R4 (low molecular weight compound HM-1/compound MC4/compound G3/compound R4= 73.9% by mass/25% by mass/1% by mass/0.1% by mass) was used in place of a low molecular weight compound HM-1, compound MC1, and compound R1 (low molecular weight compound HM-1/compound MC1/compound R1= 74% by mass/25% by mass/1% by mass) in the (Formation of Light-Emitting Layer) of Example D1.

[0562] EL emission was observed by applying a voltage to the light-emitting device D17. The EQE at 10 kcd/m2 was 6.59 [%], and the CIE chromaticity coordinate (x, y) was (0.253, 0.480). The results are shown in Table 5. Further, the LT90 at 1000 cd/m2 was 0.964 hours.

<Comparative Example CD6> Fabrication and Evaluation of Light-Emitting Device CD6



[0563] A light-emitting device CD6 was fabricated in the same manner as in Example D1, except that a low molecular weight compound HM-1, compound MC4, compound G4, and compound R4 (low molecular weight compound HM-1/compound MC4/compound G4/compound R4= 73.9% by mass/25% by mass/1% by mass/0.1% by mass) was used in place of a low molecular weight compound HM-1, compound MC1, and compound R1 (low molecular weight compound HM-1/compound MC1/compound R1= 74% by mass/25% by mass/1% by mass) in the (Formation of Light-Emitting Layer) of Example D1.

[0564] EL emission was observed by applying a voltage to the light-emitting device CD6. The EQE at 10 kcd/m2 was 6.05 [%], and the CIE chromaticity coordinate (x, y) was (0.255, 0.477). The results are shown in Table 5. Further, the LT90 at 1000 cd/m2 was 0.878 hours.

<Example D18> Fabrication and Evaluation of Light-Emitting Device D18



[0565] A light-emitting device D18 was fabricated in the same manner as in Example D1, except that a low molecular weight compound HM-1, compound MC4, compound G3, and compound R3 (low molecular weight compound HM-1/compound MC4/compound G3/compound R3= 73.9% by mass/25% by mass/1% by mass/0.1% by mass) was used in place of a low molecular weight compound HM-1, compound MC1, and compound R1 (low molecular weight compound HM-1/compound MC1/compound R1= 74% by mass/25% by mass/1% by mass) in the (Formation of Light-Emitting Layer) of Example D1.

[0566] EL emission was observed by applying a voltage to the light-emitting device D18. The EQE at 10 kcd/m2 was 7.44 [%], and the CIE chromaticity coordinate (x, y) was (0.322, 0.437). The results are shown in Table 5.

<Comparative Example CD7> Fabrication and Evaluation of Light-Emitting Device CD7



[0567] A light-emitting device CD7 was fabricated in the same manner as in Example D1, except that a low molecular weight compound HM-1, compound MC4, compound G4, and compound R3 (low molecular weight compound HM-1/compound MC4/compound G4/compound R3= 73.9% by mass/25% by mass/1% by mass/0.1% by mass) was used in place of a low molecular weight compound HM-1, compound MC1, and compound R1 (low molecular weight compound HM-1/compound MC1/compound R1= 74% by mass/25% by mass/1% by mass) in the (Formation of Light-Emitting Layer) of Example D1.

[0568] EL emission was observed by applying a voltage to the light-emitting device CD7. The EQE at 10 kcd/m2 was 5.58 [%], and the CIE chromaticity coordinate (x, y) was (0.344, 0.423). The results are shown in Table 5.
[Table 5]
 Light-Emitting DeviceLight-Emitting LayerEQE [%]CIE Chromaticity Coordinate (x, y)
CompositionComposition Ratio (% by mass)(10 kcd/m2)(10 kcd/m2)
Example D12 D12 HM-1/MC3/G6/R2 73.9/25/1/0.1 8.46 (0.393, 0.448)
Example D13 D13 HM-1/MC4/G1/R5 73.9/25/1/0.1 9.35 (0.307, 0.494)
Example D14 D14 HM-1/MC3/G3/R2 73.9/25/1/0.1 7.48 (0.282, 0.484)
Example D15 D15 HM-1/MC4/G3/R2 73.9/25/1/0.1 8.59 (0.275, 0.461)
Example D16 D16 HM-1/MC4/G3/R6 73.9/25/1/0.1 8.07 (0.387, 0.453)
Example D17 D17 HM-1/MC4/G3/R4 73.9/25/1/0.1 6.59 (0.253, 0.480)
Comparative Example CD6 CD6 HM-1/MC4/G4/R4 73.9/25/1/0.1 6.05 (0.255, 0.477)
Example D18 D18 HM-1/MC4/G3/R3 73.9/25/1/0.1 7.44 (0.322, 0.437)
Comparative Example CD7 CD7 HM-1/MC4/G4/R3 73.9/25/1/0.1 5.58 (0.344, 0.423)

Industrial Applicability



[0569] According to the present invention, a composition that is useful in fabricating a light-emitting device which shows excellent external quantum efficiency can be provided. Further, according to the present invention, a light-emitting device comprising such composition can be provided.


Claims

1. A composition, comprising:

a phosphorescent compound represented by formula (1); and

a phosphorescent compound represented by formula (2):

(wherein,

M1 represents a rhodium atom, a palladium atom, an iridium atom or a platinum atom,

n1 denotes an integer of 1 or more, n2 denotes an integer of 0 or more, and n1 + n2 is 2 or 3,

when M1 is a rhodium atom or an iridium atom, n1 + n2 is 3, and when M1 is a palladium atom or a platinum atom, n1 + n2 is 2,

ring R1A represents a triazole ring or a diazole ring constituted of a nitrogen atom, E1, E11A, E12A, and a carbon atom,

ring R2 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings each may have a substituent; when there are a plurality of such substituents, those substituents may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded; and when there are a plurality of rings R2, those rings may be the same or different,

E1, E2, E11A, and E12A each independently represent a nitrogen atom or a carbon atom; when there are a plurality of E1, E2, E11A and E12A, they may be the same or different at each occurrence; provided that at least one of E1 and E2 is a carbon atom,

R11A and R12A each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom, and these groups each may have a substituent; when there are a plurality of R11A and R12A, they may be the same or different at each occurrence; R11A and R12A may be bonded to each other to form a ring together with the atoms to which they are bonded; and R11A and an optional substituent of the ring R2 may be bonded to each other to form a ring together with the atoms to which they are bonded,

when E11A is a nitrogen atom, R11A may be present or absent, and when E12A is a nitrogen atom, R12A may be present or absent,

R13A represents an aryl group, a monovalent heterocyclic group, or a substituted amino group, and these groups each may have a substituent; when there are a plurality of R13A, they may be the same or different; and R12A and R13A may be bonded to each other to form a ring together with the atoms to which they are bonded, and

A1-G1-A2 represents an anionic bidentate ligand, A1 and A2 each independently represent a carbon atom, an oxygen atom or a nitrogen atom, and these atoms may be atoms constituting a ring; G1 represents a single bond or an atomic group constituting the bidentate ligand together with A1 and A2; and when there are a plurality of A1-G1-A2, they may be the same or different)

(wherein,

M2 represents a rhodium atom, a palladium atom, an iridium atom or a platinum atom,

n3 denotes an integer of 1 or more, n4 denotes an integer of 0 or more, and n3 + n4 is 2 or 3; when M2 is a rhodium atom or an iridium atom, n3 + n4 is 3; and when M2 is a palladium atom or a platinum atom, n3 + n4 is 2,

EL represents a carbon atom or a nitrogen atom,

ring L1 represents a 6-membered aromatic heterocyclic ring, which may have a substituent; when there are a plurality of such substituents, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded; and when there are a plurality of rings L1, they may be the same or different,

ring L2 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings each may have a substituent; when there are a plurality of such substituents, they may be the same or

different and may be bonded to each other to form a ring together with the atoms to which they are bonded; and when there are a plurality of rings L2, they may be the same or different,

an optional substituent of the ring L1 and an optional substituent of the ring L2 may combine with each other to form a ring together with the atoms to which they are bonded,

provided that at least one ring selected from the group consisting of ring L1 and ring L2 has at least one group represented by formula (1-T); and when there are a plurality of groups represented by formula (1-T), they may be the same or different,

A3-G2-A4 represents an anionic bidentate ligand, A3 and A4 each independently represent a carbon atom, an oxygen atom or a nitrogen atom, and these atoms may be atoms constituting a ring; G2 represents a single bond or an atomic group constituting the bidentate ligand together with A3 and A4; and when there are a plurality of A3-G2-A4, they may be the same or different)
[Chemical Formula 3]

        -R1T     (1-T)

(wherein,
R1T represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryloxy group, a halogen atom, an aryl group, a monovalent heterocyclic group, or a substituted amino group, and these groups each may have a substituent).


 
2. The composition according to claim 1, wherein the phosphorescent compound represented by formula (2) is a phosphorescent compound represented by formula (2-B):

(wherein,

M2, n3, n4, and A3-G2-A4 have the same meaning as described above,

E11B, E12B, E13B, E14B, E21B, E22B, E21B, and E24B each independently represent a nitrogen atom or a carbon atom; when there are a plurality of E11B, E12B, E13B, E14B, E21B, E22B, E23B, and E24B, they may be the same or different at each occurrence; when E11B is a nitrogen atom, R11B is absent; when E12B is a nitrogen atom, R12B is absent, when E13B is a nitrogen atom, R13B is absent; when E14B is a nitrogen atom, R14B is absent; when E21B is a nitrogen atom, R21B is absent; when E22B is a nitrogen atom, R22B is absent; when E23B is a nitrogen atom, R23B is absent; and when E24B is a nitrogen atom, R24B is absent,

R11B, R12B, R13B, R14B, R21B, R22B, R23B, and R24B each independently represent a hydrogen atom or a group represented by formula (1-T); when there are a plurality of R11B, R12B, R13B, R14B, R21B, R22B, R23B, and R24B, they may be the same or different at each occurrence; and R11B and R12B, R12B and R13B, R13B and R14B, R11B and R21B, R21B and R22B, R22B and R23B, and R23B and R24B each may be bonded to each other to form a ring together with the atoms to which they are bonded, provided that at least one selected from the group consisting of R11B, R12B, R13B, R14B, R21B, R22B, R23B, and R24B is a group represented by formula (1-T),

ring L1B represents a pyridine ring or a pyrimidine ring constituted of a nitrogen atom, a carbon atom, E11B, E12B, E13B, and E14B, and

ring L2B represents a benzene ring, a pyridine ring, or a pyrimidine ring constituted of two carbon atoms, E21B, E22B, E23B, and E24B).


 
3. The composition according to claim 2, wherein the phosphorescent compound represented by formula (2-B) is a phosphorescent compound represented by formula (2-B1), a phosphorescent compound represented by formula (2-B2), a phosphorescent compound represented by formula (2-B3), a phosphorescent compound represented by formula (2-B4), or a phosphorescent compound represented by formula (2-B5):



(wherein,

M2, n3, n4, R11B, R12B, R13B, R14B, R21B, R22B, R23B, R24B, and A3-G2-A4 have the same meanings as described above,

n31 and n32 each independently denote an integer of 1 or more, and n31 + n32 is 2 or 3; when M2 is a rhodium atom or an iridium atom, n31 + n32 is 3; and when M2 is a palladium atom or a platinum atom, n31 + n32 is 2, and

R15B, R16B, R17B, and R18B each independently represent a hydrogen atom or a group represented by formula (1-T); when there are a plurality of R15B, R16B, R17B, and R18B, they may be the same or different at each occurrence; R15B and R16B, R16B and R17B, and R17B and R18B each may be bonded to each other to form a ring together with the atoms to which they are bonded,

provided that, in formulas (2-B1) and (2-B3), at least one selected from the group consisting of R11B, R12B, R13B, R14B, R21B, R22B, R23B, and R24B is a group represented by formula (1-T); in formula (2-B2), at least one selected from the group consisting of R13B R14B, R21B, R22B, R23B, and R24B is a group represented by formula (1-T); in formula (2-B4), at least one selected from the group consisting of R11B, R14B, R21B, R22B, R23B, and R24B is a group represented by formula (1-T); and in formula (2-B5), at least one selected from the group consisting of R11B, R12B, R21B, R22B, R23B, and R24B is a group represented by formula (1-T)).


 
4. The composition according to any one of claims 1 to 3, wherein R1T is an alkyl group, a cycloalkyl group, a group represented by formula (D-A), a group represented by formula (D-B), or a group represented by formula (D-C):

(wherein,

mDA1, mDA2, and mDA3 each independently denote an integer of 0 or more,

GDA represents a nitrogen atom, an aromatic hydrocarbon group, or a heterocyclic group, and these groups each may have a substituent,

ArDA1, ArDA2, and ArDA3 each independently represent an arylene group or a divalent heterocyclic group, and these groups each may have a substituent; and when there are a plurality of ArDA1, ArDA2, and ArDA3, they may be the same or different at each occurrence, and

TDA represents an aryl group or a monovalent heterocyclic group, and these groups each may have a substituent; and the plurality of TDA may be the same or different)

(wherein,

mDA1, mDA2, mDA3, mDA4, mDA5, mDA6, and mDA7 each independently denote an integer of 0 or more,

GDA represents a nitrogen atom, an aromatic hydrocarbon group, or a heterocyclic group, and these groups each may have a substituent; and the plurality of GDA may be the same or different,

ArDA1, ArDA2, ArDA3, ArDA4, ArDA5, ArDA6, and ArDA7 each independently represent an arylene group or a divalent heterocyclic group, and these groups each may have a substituent; and when there are a plurality of ArDA1, ArDA2, ArDA3, ArDA4, ArDA5, ArDA6, and ArDA7, they may be the same or different at each occurrence, and

TDA represents an aryl group or a monovalent heterocyclic group, and these groups each may have a substituent; and the plurality of TDA may be the same or different), and

(wherein,

mDA1 denotes an integer of 0 or more,

ArDA1 represents an arylene group or a divalent heterocyclic group, and these groups each may have a substituent; and when there are a plurality of ArDA1, they may be the same or different, and

TDA represents an aryl group or a monovalent heterocyclic group, and these groups each may have a substituent).


 
5. The composition according to claim 4,
wherein R1T is a group represented by formula (D-A), and
wherein the group represented by formula (D-A) is a group represented by formula (D-A1), a group represented by formula (D-A2), a group represented by formula (D-A3), or a group represented by formula (D-A4),



(wherein,

Rp1, Rp2, Rp3, and Rp4 each independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or a halogen atom; and when there are a plurality of Rp1, Rp2, and Rp4, they may be the same or different at each occurrence, and

np1 denotes an integer of 0 to 5, np2 denotes an integer of 0 to 3, np3 represents 0 or 1, and np4 denotes an integer of 0 to 4; and the plurality of np1 may be the same or different).


 
6. The composition according to claim 4,
wherein R1T is a group represented by formula (D-B), and
wherein the group represented by formula (D-B) is a group represented by formula (D-B1), a group represented by formula (D-B2), or a group represented by formula (D-B3):



(wherein,

Rp1, Rp2, and Rp3 each independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or a halogen atom; and when there are a plurality of Rp1 and Rp2, they may be the same or different at each occurrence, and

np1 denotes an integer of 0 to 5, np2 denotes an integer of 0 to 3, and np3 represents 0 or 1; and when there are a plurality of np1 and np2, they may be the same or different at each occurrence).


 
7. The composition according to claim 4,
wherein R1T is a group represented by formula (D-C), and
wherein the group represented by formula (D-C) is a group represented by formula (D-C1), a group represented by formula (D-C2), a group represented by formula (D-C3), or a group represented by formula (D-C4):



(wherein,

Rp4, Rp5, and Rp6 each independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or a halogen atom; and when there are a plurality of Rp4, Rp5, and Rp6, they may be the same or different at each occurrence, and

np4 denotes an integer of 0 to 4, np5 denotes an integer of 0 to 5, and np6 denotes an integer of 0 to 5).


 
8. The composition according to any one of claims 1 to 7, wherein the phosphorescent compound represented by formula (1) is a phosphorescent compound represented by formula (1-A):

(wherein,

M1, n1, n2, ring R1A, E1, E11A, E12A, R11A, R12A, R13A, and A1-G1-A2 have the same meanings as described above,

ring R2A represents a benzene ring, a pyridine ring, or a pyrimidine ring constituted of two carbon atoms, E21A, E22A, E23A, and E24A,

E21A, E22A, E23A, and E24A, each independently represent a nitrogen atom or a carbon atom; when there are a plurality of E21A, E22A, E23A, and E24A, they may be the same or different at each occurrence; when E21A is a nitrogen atom, R21A is absent; when E22A is a nitrogen atom, R22A is absent; when E23A is a nitrogen atom, R23A is absent; and when E24A, is a nitrogen atom, R24A is absent, and

R21A, R22A, R23A, and R24A each represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom, and these groups each may have a substituent; when there are a plurality of R21A, R22A, R23A, and R24A, they may be the same or different at each occurrence; R21A and R22A may be bonded to each other to form a ring together with the atoms to which they are bonded; R22A and R23A may be bonded to each other to form a ring together with the atoms to which they are bonded; R23A and R24A may be bonded to each other to form a ring together with the atoms to which they are bonded; and R11A and R21A may be bonded to each other to form a ring together with the atoms to which they are bonded).


 
9. The composition according to claim 8, wherein the phosphorescent compound represented by formula (1-A) is a phosphorescent compound represented by formula (1-A1), a phosphorescent compound represented by formula (1-A2), a phosphorescent compound represented by formula (1-A3), or a phosphorescent compound represented by formula (1-A4):

(wherein M1, n1, n2, R11A, R12A, R13A, R21A, R22A, R23A, R24A, and A1-G1-A2 have the same meanings as described above).
 
10. The composition according to any one of claims 1 to 9, wherein R13A is an aryl group which may have a substituent.
 
11. The composition according to any one of claims 1 to 10, wherein the composition comprises two or more phosphorescent compounds represented by formula (2).
 
12. The composition according to any one of claims 1 to 11,
wherein the maximum peak wavelength of the emission spectrum of the phosphorescent compound represented by formula (1) is 380 nm or more and less than 495 nm, and
wherein the maximum peak wavelength of the emission spectrum of the phosphorescent compound represented by formula (2) is 495 nm or more and less than 750 nm.
 
13. The composition according to any one of claims 1 to 12, further comprising a compound represented by formula (H-1):

(wherein,

ArH1 and ArH2 each independently represent an aryl group or a monovalent heterocyclic group, and these groups each may have a substituent,

nH1 and nH2 each independently denote 0 or 1; when there are a plurality of nH1, they may be the same or different; and the plurality of nH2 may be the same or different,

nH3 denotes an integer of 0 or more,

LH1 represents an arylene group, a divalent heterocyclic group, or a group represented by -[C(RH11)2]nH11-, and these groups each may have a substituent; when there are a plurality of LH1, they may be the same or different,

nH11 denotes an integer of 1 or more and 10 or less; RH11 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups each may have a substituent; and the plurality of RH11 may be the same or different and may be bonded to each other to form a ring together with the carbon atom to which they are bonded,

LH2 represents a group represented by -N(-LH21-RH21)-; when there are a plurality of LH2, they may be the same or different, and

LH21 represents a single bond, an arylene group, or a divalent heterocyclic group, and these groups each may have a substituent; RH21 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups each may have a substituent).


 
14. The composition according to any one of claims 1 to 13, further comprising at least one material selected from the group consisting of a hole transporting material, a hole injecting material, an electron transporting material, an electron injecting material, a light emitting material, an antioxidant, and a solvent.
 
15. A light-emitting device, comprising:

an anode;

a cathode; and

a layer provided between the anode and the cathode, and comprising the composition according to any one of claims 1 to 14.


 











REFERENCES CITED IN THE DESCRIPTION



This list of references cited by the applicant is for the reader's convenience only. It does not form part of the European patent document. Even though great care has been taken in compiling the references, errors or omissions cannot be excluded and the EPO disclaims all liability in this regard.

Patent documents cited in the description




Non-patent literature cited in the description