Light-emitting device and composition useful for producing the light-emitting device

Abstract

The present invention provides a light-emitting element with excellent external quantum efficiency. A light-emitting element is a light-emitting element having an anode, a cathode, a first organic layer disposed between the anode and the cathode, and a second organic layer disposed between the anode and the cathode, wherein the first organic layer is a layer containing a compound (T) having an absolute value of a difference between an energy level of a lowest triplet excited state and an energy level of a lowest singlet excited state of 0.5 eV or less, and does not contain a phosphorescent metal complex, and the second organic layer is a layer containing a crosslinked body of a polymer compound containing a crosslinked structural unit, and the energy level of the lowest triplet excited state of the polymer compound is 2.25 eV or more.

Description

[0001] This application is a divisional application of the application with international application number PCT / JP2017 / 034966, entry into the Chinese national phase date of March 26, 2019, national application number 201780059346.0, and invention name “Light-emitting element and composition useful for manufacturing the same”. Technical Field

[0002] The present invention relates to a light-emitting device and a composition useful for producing the light-emitting device. Background Art

[0003] Organic electroluminescent elements (hereinafter also referred to as light-emitting elements) can be suitably used in display and lighting applications, and therefore research and development have been carried out. For example, Patent Document 1 describes a light-emitting element having: an organic layer containing a polymer compound (P-2) represented by the following formula and a light-emitting layer containing a light-emitting material having a carbazole skeleton.

[0004] [Chemistry 1]

[0005]

[0006] Prior art literature

[0007] Patent Literature

[0008] Patent Document 1: International Publication No. 2016 / 091351 Summary of the invention

[0009] Problems to be solved by the invention

[0010] However, the external quantum efficiency of the above-mentioned light-emitting element is not necessarily sufficient.

[0011] Therefore, an object of the present invention is to provide a light-emitting device having excellent external quantum efficiency. Another object of the present invention is to provide a composition useful for producing the light-emitting device.

[0012] Means for solving problems

[0013] The present invention provides the following [1] to

[13] .

[0014] [1] A light-emitting element comprising an anode, a cathode, a first organic layer provided between the anode and the cathode, and a second organic layer provided between the anode and the cathode,

[0015] The first organic layer is a layer containing a compound (T) having an absolute value of a difference between an energy level of a lowest triplet excited state and an energy level of a lowest singlet excited state of 0.5 eV or less, and does not contain a phosphorescent metal complex.

[0016] The second organic layer is a layer containing a crosslinked body of a polymer compound including a crosslinked structural unit, and the energy level of the lowest triplet excited state of the polymer compound is 2.25 eV or more.

[0017] [2] The light-emitting element according to [1], wherein the cross-linked structural unit is a structural unit having at least one cross-linked group selected from the cross-linked group A group.

[0018] (Cross-linking group A)

[0019] [Chemistry 2]

[0020]

[0021] [Where R XL represents a methylene group, an oxygen atom or a sulfur atom, n XL represents an integer from 0 to 5. XL In the case of n, they are optionally the same or different. XL In the case of, they are optionally the same or different. *1 represents the bonding position. These crosslinking groups may optionally have a substituent. ]

[0022] [3] The light-emitting element according to [2], wherein the cross-linked structural unit is a structural unit represented by formula (2) or a structural unit represented by formula (2′).

[0023] [Chemistry 3]

[0024]

[0025] [Wherein,

[0026] nA represents an integer of 0 to 5, and n represents 1 or 2. When a plurality of nA are present, they may be the same or different.

[0027] Ar 3 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent.

[0028] L A represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -N(R')-, an oxygen atom or a sulfur atom, and these groups 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 may have a substituent. A In the case of , they are optionally the same or different.

[0029] X represents a crosslinking group selected from the crosslinking group group A. When there are multiple Xs, they are optionally the same or different.]

[0030] [Chemistry 4]

[0031]

[0032] [Wherein,

[0033] mA represents an integer of 0 to 5, m represents an integer of 1 to 4, and c represents 0 or 1. When a plurality of mAs are present, they may be the same or different.

[0034] Ar 5 It 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 have a substituent.

[0035] Ar 4 and Ar 6 Each independently represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent.

[0036] Ar 4 ,Ar 5 and Ar 6 They may each form a ring by directly bonding to a group other than the group bonded to the nitrogen atom to which the group is bonded, or by bonding via an oxygen atom or a sulfur atom.

[0037] K A represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -N(R')-, an oxygen atom or a sulfur atom, and these groups may optionally have a substituent. R' represents the same meaning as above. A In the case of , they are optionally the same or different.

[0038] X' represents a crosslinking group selected from the crosslinking group group A, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may optionally have a substituent. In the case where there are multiple X's, they may be the same or different. However, at least one X' is a crosslinking group selected from the crosslinking group group A.]

[0039] [4] The light-emitting element according to any one of [1] to [3], wherein the compound (T) is a compound represented by formula (T-1).

[0040] [Chemistry 5]

[0041]

[0042] [Wherein,

[0043] n T1 represents an integer greater than or equal to 0 and less than or equal to 5. T1 In the case of , they are optionally the same or different.

[0044] Ar T1represents an aryl group, a substituted amino group or a monovalent heterocyclic group, and these groups may have a substituent. T1 In the case of, they are optionally the same or different, and optionally directly bonded or bonded via a divalent group to form a ring. T1 is a substituted amino group, or contains a nitrogen atom having no double bond in the ring and does not contain a group represented by =N- in the ring, a boron atom, -C(=Z T1 )-, -S(=O)-, -S(=O)2-, and a monovalent heterocyclic group represented by formula (P). T1 represents an oxygen atom, a sulfur atom or =N(R ZT1 ) shown in the figure. ZT1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.

[0045] [Chemistry 6]

[0046]

[0047] L T1 represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, -N(R T1 ')-, an oxygen atom or a sulfur atom, which may have a substituent. T1 ' represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. T1 In the case of , they are optionally the same or different, and optionally bonded directly or via a divalent group to form a ring.

[0048] Ar T2 is a boron atom, -C(=Z T1 )-, a group represented by -S(=O)-, a group represented by -S(=O)2-, a group represented by the above formula (P), an aromatic hydrocarbon group having an electron-withdrawing group, or a heterocyclic group containing a group represented by =N- in the ring, and these groups optionally have substituents.

[0049] n 12 represents an integer of 1 to 15. T2 When it is a boron atom or a group represented by the above formula (P), n T2 is 3. T2 =Z T1 In the case of a group represented by -S(=O)-, a group represented by -S(=O)-, or a group represented by -S(=O)2-, n T2 is 2.

[0050] Ar T1 With LT1 Ar is optionally bonded directly or via a divalent group to form a ring. T2 With L T1 Ar is optionally bonded directly or via a divalent group to form a ring. T1 with Ar T2 Optionally, they are directly bonded or bonded via a divalent group to form a ring.]

[0051] [5] The light-emitting element according to [4], wherein at least one of the Ar T1 It is a group represented by formula (T1-1).

[0052] [Chemistry 7]

[0053]

[0054] [Wherein,

[0055] Ring R T1 and Ring R T2 Each independently indicates that the ring does not contain -C (=Z T1 )-, or an aromatic hydrocarbon ring containing no group represented by =N-, a boron atom, -C(=Z T1 )-, -S(=O)-, -S(=O)2-, and a heterocyclic ring of a group represented by the above formula (P), and these rings may have a substituent. T1 Means the same as above.

[0056] X T1 represents a single bond, oxygen atom, sulfur atom, -N(R XT1 )- or -C(R XT1 ')2-. XT1 and R XT1 ' each independently represents 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, a halogen atom or a cyano group, and these groups may have a substituent. XT1 ' are optionally the same or different, and are optionally bonded to each other and together with the carbon atom to which they are bonded to form a ring.

[0057] R XT1 and Ring R T1 The optional substituents, R XT1 and Ring R T2 The optional substituents, R XT1 ′ and ring R T1 The optional substituents, and R XT1 ′ and ring R T2The substituents optionally possessed are optionally bonded directly or via a divalent group, respectively, and together with the atoms to which they are bonded, form a ring.]

[0058] [6] The light-emitting element according to [5], wherein the group represented by the above formula (T1-1) is a group represented by formula (T1-1A), a group represented by formula (T1-1B), a group represented by formula (T1-1C) or a group represented by formula (T1-1D).

[0059] [Chemistry 8]

[0060]

[0061] [Wherein,

[0062] X T1 Means the same as above.

[0063] X T2 and X T3 Each independently represents a single bond, an oxygen atom, a sulfur atom, -N(R XT2 )- or -C(R XT2 ')2-. XT2 and R XT2 ' each independently represents 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, a halogen atom or a cyano group, and these groups may have a substituent. XT2 ' are optionally the same or different, optionally bonded directly or via a divalent group and together with the carbon atom to which they are each bonded form a ring.

[0064] R T1 , R T2 , R T3 , R T4 , R T5 , R T6 , R T7 , R T8 , R T9 , R T10 , R T11 and R T12 Each independently represents 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, a halogen atom or a cyano group, and these groups may have a substituent.

[0065] R T1 With R T2 , R T2 With R T3 , R T3 With R T4 , R T5 With RT6 , RT 6 With RT 7 , R T7 With R T8 , R T9 With R T10 , R T10 With R T11 , and R T11 With R T12 Optionally, they are each directly bonded or bonded via a divalent group and together with the carbon atom to which they are bonded, form a ring.]

[0066] [7] The light-emitting element according to any one of [4] to [6], wherein the Ar T2 It is a heterocyclic group containing a group represented by =N- in the ring (the group may have a substituent).

[0067] [8] The light-emitting element according to [7], wherein the Ar T2 It is a group obtained by removing one or more hydrogen atoms directly bonded to atoms constituting the ring from a diazole ring, a triazole ring, an oxadiazole ring, a thiadiazole ring, a thiazole ring, an oxazole ring, an isothiazole ring, an isoxazole ring, a benzodiazole ring, a benzotriazole ring, a benzoxadiazole ring, a benzothiadiazole ring, a benzothiazole ring, a benzoxazole ring, an azacarbazole ring, a diazacarbazole ring, a pyridine ring, a diazobenzene ring, a triazine ring, a naphthyrazine ring, a naphthyrazine ring, a triazine ring, a tetraazine ring, an azaanthracene ring, a diazaanthracene ring, a triazaanthracene ring, a tetraazaanthracene ring, an azaphenanthracene ring, a diazophanthracene ring, a triazophanthracene ring or a tetraazophanthracene ring (the group may have a substituent).

[0068] [9] The light-emitting element according to any one of [1] to [8], wherein the oscillator strength of the compound (T) is 0.0001 or more.

[0069]

[10] The light-emitting element according to any one of [1] to [9], wherein the first organic layer further contains at least one selected from a host material, a hole transport material, a hole injection material, an electron transport material, an electron injection material, a fluorescent material and an antioxidant.

[0070]

[11] The light-emitting element according to any one of [1] to

[10] , wherein the first organic layer is adjacent to the second organic layer.

[0071]

[12] The light-emitting element according to any one of [1] to

[11] , wherein the second organic layer is a layer provided between the anode and the first organic layer.

[0072]

[13] A composition comprising a compound (T) having an absolute value of a difference between the energy level of the lowest triplet excited state and the energy level of the lowest singlet excited state of 0.5 eV or less and a polymer compound comprising a structural unit represented by formula (Y), and containing no phosphorescent metal complex.

[0073] [Chemistry 9]

[0074]

[0075] [Wherein, Ar Y1 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, and these groups may have a substituent.]

[0076] Effects of the Invention

[0077] According to the present invention, a light-emitting device having excellent external quantum efficiency and a composition useful for producing the light-emitting device can be provided. DETAILED DESCRIPTION

[0078] Hereinafter, preferred embodiments of the present invention will be described in detail.

[0079] <Explanation of General Terms>

[0080] The terms commonly used in this specification have the following meanings unless otherwise specified.

[0081] 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.

[0082] The hydrogen atom may be a deuterium atom or a protium atom.

[0083] In the formula representing the metal complex, the solid line representing the bond with the central metal means a covalent bond or a coordinate bond.

[0084] The term "polymer compound" means a compound having a molecular weight distribution and a polystyrene-equivalent number average molecular weight of 1×10 3 ~1×10 8 of polymers.

[0085] The polymer compound may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, and may be in other forms.

[0086] Regarding the terminal group of the polymer compound, if the polymerization active group remains as it is, when the polymer compound is used for the preparation of a light-emitting element, there is a possibility that the luminous properties or brightness life will be reduced, so a stable group is preferably used. As the terminal group of the polymer compound, it is preferably a group conjugated with the main chain, and for example, an aryl group bonded to the main chain of the polymer compound through a carbon-carbon bond or a group bonded to a monovalent heterocyclic group can be cited.

[0087] A "low molecular weight compound" is a compound that has no molecular weight distribution and has a molecular weight of 1×10 4 The following compounds.

[0088] The term "structural unit" refers to a unit existing at least one unit in a polymer compound.

[0089] The "alkyl group" may be either a straight chain or a branched chain. The number of carbon atoms in a straight chain alkyl group does not include the number of carbon atoms in the substituent, and is usually 1 to 50, preferably 3 to 30, and more preferably 4 to 20. The number of carbon atoms in a branched chain alkyl group does not include the number of carbon atoms in the substituent, and is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20.

[0090] The alkyl group may have a substituent, and examples thereof include methyl, ethyl, propyl, isopropyl, butyl, 2-butyl, isobutyl, tert-butyl, pentyl, isopentyl, 2-ethylbutyl, hexyl, heptyl, octyl, 2-ethylhexyl, 3-propylheptyl, decyl, 3,7-dimethyloctyl, 2-ethyloctyl, 2-hexyldecyl, dodecyl, and groups in which hydrogen atoms in these groups are substituted with cycloalkyl, alkoxy, cycloalkoxy, aryl, fluorine atoms, etc. (for example, trifluoromethyl, pentafluoroethyl, perfluorobutyl, perfluorohexyl, perfluorooctyl, 3-phenylpropyl, 3-(4-methylphenyl)propyl, 3-(3,5-dihexylphenyl)propyl, and 6-ethoxyhexyl).

[0091] The number of carbon atoms in the "cycloalkyl group" is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20, not including the number of carbon atoms in the substituent.

[0092] The cycloalkyl group may have a substituent, and examples thereof include a cyclohexyl group, a cyclohexylmethyl group, and a cyclohexylethyl group.

[0093] "Aryl" refers to an atomic group remaining after removing one hydrogen atom directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon. The number of carbon atoms in an aryl group does not include the number of carbon atoms in a substituent, and is usually 6 to 60, preferably 6 to 20, and more preferably 6 to 10.

[0094] The aryl group may have a substituent, and examples thereof include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 2-phenylphenyl, 3-phenylphenyl, 4-phenylphenyl, and groups in which hydrogen atoms in these groups are substituted with alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkyloxy groups, aryl groups, fluorine atoms, or the like.

[0095] The "alkoxy group" may be either linear or branched. The number of carbon atoms in a linear alkoxy group does not include the number of carbon atoms in the substituent, and is usually 1 to 40, preferably 4 to 10. The number of carbon atoms in a branched alkoxy group does not include the number of carbon atoms in the substituent, and is usually 3 to 40, preferably 4 to 10.

[0096] The alkoxy group may have a substituent, and examples thereof include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a tert-butoxy 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, a lauryloxy group, and groups in which hydrogen atoms in these groups are substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like.

[0097] The number of carbon atoms in the "cycloalkoxy group" is usually 3 to 40, preferably 4 to 10, not including the number of carbon atoms in the substituent.

[0098] The cycloalkoxy group may have a substituent, and an example thereof is a cyclohexyloxy group.

[0099] The number of carbon atoms in the "aryloxy group" is usually 6 to 60, preferably 6 to 48, not including the number of carbon atoms in the substituent.

[0100] The aryloxy group may have a substituent, and examples thereof include phenoxy, 1-naphthyloxy, 2-naphthyloxy, 1-anthryloxy, 9-anthryloxy, 1-pyreneoxy, and groups in which hydrogen atoms in these groups are substituted with alkyl, cycloalkyl, alkoxy, cycloalkyloxy, fluorine atoms or the like.

[0101] "P-valent heterocyclic group" (p represents an integer greater than or equal to 1) refers to an atomic group remaining after removing p hydrogen atoms directly bonded to carbon atoms or heteroatoms constituting the ring from a heterocyclic compound. Among p-valent heterocyclic groups, an atomic group remaining after removing p hydrogen atoms directly bonded to carbon atoms or heteroatoms constituting the ring from an aromatic heterocyclic compound, i.e., a "p-valent aromatic heterocyclic group" is preferred.

[0102] "Aromatic heterocyclic compounds" refer to: compounds in which the heterocyclic rings such as oxadiazole, thiadiazole, thiazole, oxazole, thiophene, pyrrole, phosphole, furan, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole, dibenzophosphole, etc. themselves exhibit aromatic properties; and compounds in which the heterocyclic rings such as phenoxazine, phenothiazine, dibenzoborole, dibenzosilole, benzopyran, etc. themselves do not exhibit aromatic properties but have aromatic rings condensed on the heterocyclic rings.

[0103] The number of carbon atoms in the monovalent heterocyclic group is usually 2 to 60, preferably 4 to 20, not including the number of carbon atoms in the substituent.

[0104] The monovalent heterocyclic group may have a substituent, and examples thereof include thienyl, pyrrolyl, furyl, pyridyl, piperidyl, quinolyl, isoquinolyl, pyrimidyl, triazinyl, and groups in which hydrogen atoms in these groups are substituted with alkyl, cycloalkyl, alkoxy, cycloalkoxy or the like.

[0105] The "halogen atom" means a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0106] The "amino group" may have a substituent, and is preferably a substituted amino group. The substituent of the amino group is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group.

[0107] Examples of the substituted amino group include a dialkylamino group, a dicycloalkylamino group, and a diarylamino group.

[0108] 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.

[0109] The "alkenyl group" may be either a straight chain or a branched chain. The number of carbon atoms in a straight chain alkenyl group does not include the number of carbon atoms in the substituent, and is usually 2 to 30, preferably 3 to 20. The number of carbon atoms in a branched chain alkenyl group does not include the number of carbon atoms in the substituent, and is usually 3 to 30, preferably 4 to 20.

[0110] The number of carbon atoms in the "cycloalkenyl group" is usually 3 to 30, preferably 4 to 20, not including the number of carbon atoms in the substituent.

[0111] The alkenyl group and the cycloalkenyl group may have a substituent, and examples thereof include vinyl, 1-propenyl, 2-propenyl, 2-butenyl, 3-butenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 5-hexenyl, 7-octenyl, and groups in which these groups have a substituent.

[0112] The "alkynyl group" may be either a straight chain or a branched chain. The number of carbon atoms of the alkynyl group does not include the carbon atoms of the substituent, and is usually 2 to 20, preferably 3 to 20. The number of carbon atoms of the branched alkynyl group does not include the carbon atoms of the substituent, and is usually 4 to 30, preferably 4 to 20.

[0113] The number of carbon atoms in the "cycloalkynyl group" is usually 4 to 30, preferably 4 to 20, not including the carbon atoms in the substituent.

[0114] The alkynyl group and cycloalkynyl group may have a substituent, and examples thereof include ethynyl, 1-propynyl, 2-propynyl, 2-butynyl, 3-butynyl, 3-pentynyl, 4-pentynyl, 1-hexynyl, 5-hexynyl, and groups in which these groups have a substituent.

[0115] "Arylene" refers to an atomic group remaining after removing two hydrogen atoms directly bonded to carbon atoms constituting a ring from an aromatic hydrocarbon. The number of carbon atoms in the arylene group is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18, excluding the number of carbon atoms in the substituent.

[0116] The arylene group may have a substituent, and examples thereof include phenylene, naphthalene diyl, anthracene diyl, phenanthrene diyl, dihydrophenanthrene diyl, naphthacene diyl, fluorene diyl, pyrene diyl, perylene diyl, The diradical and the groups in which these groups have substituents are preferably groups represented by formula (A-1) to formula (A-20). The arylene group includes a group in which a plurality of these groups are bonded.

[0117] [Chemistry 10]

[0118]

[0119] [Chemistry 11]

[0120]

[0121] [Chemistry 12]

[0122]

[0123] [Chemistry 13]

[0124]

[0125] [where R and R a Each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group. a The same or different, R a They are optionally bonded to each other and together with the atoms to which they are bonded form a ring.]

[0126] The number of carbon atoms in the divalent heterocyclic group is usually 2 to 60, preferably 3 to 20, and more preferably 4 to 15, not including the number of carbon atoms in the substituent.

[0127] The divalent heterocyclic group may optionally have a substituent, and examples thereof include: a divalent group obtained by removing two hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring from pyridine, benzene, triazine, naphthyrazine, naphthyrazine, carbazole, dibenzofuran, dibenzothiophene, dibenzosilole, phenoxazine, phenothiazine, acridine, dihydroacridine, furan, thiophene, oxadiazole, diazole, triazole, and preferably a group represented by formula (AA-1) to formula (AA-34). The divalent heterocyclic group includes a group to which a plurality of these groups are bonded.

[0128] [Chemistry 14]

[0129]

[0130] [Chemistry 15]

[0131]

[0132] [Chemistry 16]

[0133]

[0134] [Chemistry 17]

[0135]

[0136] [Chemistry 18]

[0137]

[0138] [Chemistry 19]

[0139]

[0140] [Chemistry 20]

[0141]

[0142] [where R and R a Means the same as above.]

[0143] The "cross-linking group" is a group that can generate new bonds by subjecting to heat treatment, ultraviolet irradiation treatment, near-ultraviolet irradiation treatment, visible light irradiation treatment, infrared irradiation treatment, free radical reaction, etc., and is preferably a cross-linking group represented by formula (XL-1) to formula (XL-17) of the above-mentioned cross-linking group A group.

[0144] The "substituent" means a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkyloxy 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 be a crosslinking group.

[0145] <Light-emitting device>

[0146] The light-emitting element of the present invention is a light-emitting element comprising an anode, a cathode, a first organic layer provided between the anode and the cathode, and a second organic layer provided between the anode and the cathode.

[0147] The first organic layer is a layer having an absolute value of a difference between an energy level of a lowest triplet excited state and an energy level of a lowest singlet excited state (hereinafter also referred to as "ΔE ST ”) is a compound (T) with a V of 0.5 eV or less and does not contain a phosphorescent metal complex,

[0148] The second organic layer is a layer containing a crosslinked body of a polymer compound including a crosslinked structural unit, and the energy level of the lowest triplet excited state of the polymer compound is 2.25 eV or more.

[0149] The phosphorescent metal complex is a metal complex that emits light from a triplet excited state at room temperature (25° C.).

[0150] Examples of the method for forming the first organic layer and the second organic layer include dry methods such as vacuum deposition and wet methods such as spin coating and inkjet printing, and wet methods are preferred.

[0151] When the first organic layer is formed by a wet method, it is preferable to use a first ink described later.

[0152] When the second organic layer is formed by a wet method, it is preferred to use the second ink described later. By heating or light irradiation after forming the second organic layer, the polymer compound containing a cross-linked structural unit (i.e., a structural unit having a cross-linking group) contained in the second organic layer can be cross-linked, preferably by heating to cross-link the polymer compound containing a cross-linked structural unit contained in the second organic layer. The second organic layer contains a polymer compound containing a cross-linked structural unit in a cross-linked state (a cross-linked body of a polymer compound containing a cross-linked structural unit), and therefore, the second organic layer is substantially insoluble in a solvent. Therefore, the second organic layer can be suitably used for the stacking of light-emitting elements.

[0153] The heating temperature for cross-linking is usually 25°C to 300°C, preferably 50°C to 260°C, more preferably 130°C to 230°C, and further preferably 180°C to 210°C.

[0154] The heating time is usually 0.1 to 1000 minutes, preferably 0.5 to 500 minutes, more preferably 1 to 120 minutes, and further preferably 10 to 60 minutes.

[0155] The type of light used for light irradiation is, for example, ultraviolet light, near-ultraviolet light, and visible light.

[0156] As analysis methods for the components contained in the first organic layer or the second organic layer, for example: chemical separation analysis methods such as extraction; equipment analysis methods such as infrared spectroscopy (IR), nuclear magnetic resonance spectroscopy (NMR), mass spectrometry (MS); and analysis methods combining chemical separation analysis methods with equipment analysis methods.

[0157] By using an organic solvent such as toluene, xylene, chloroform, tetrahydrofuran, etc. to perform solid-liquid extraction on the first organic layer or the second organic layer, it can be separated into a component that is substantially insoluble in the organic solvent (insoluble component) and a component that is soluble in the organic solvent (soluble component). The insoluble component can be analyzed by infrared spectroscopy or nuclear magnetic resonance spectroscopy, and the soluble component can be analyzed by nuclear magnetic resonance spectroscopy or mass spectrometry.

[0158] <First organic layer>

[0159] [Compound (T)]

[0160] The compound (T) is preferably a thermally activated delayed fluorescence (TADF) material. The TADF material is preferably a low molecular weight compound.

[0161] ΔE of compound (T) ST It is preferably 0.45 eV or less, more preferably 0.40 eV or less, further preferably 0.30 eV or less, particularly preferably 0.20 eV or less, particularly preferably 0.13 eV or less, and particularly more preferably 0.11 eV or less. ΔE of compound (T) ST It is preferably 0.0001 eV or more, more preferably 0.001 eV or more, further preferably 0.005 eV or more, and particularly preferably 0.01 eV or more. From the viewpoint of excellent external quantum efficiency of the light-emitting device of the present invention, the ΔE of compound (T) ST It is preferably 0.0001 eV to 0.45 eV, more preferably 0.0001 eV to 0.40 eV, further preferably 0.001 eV to 0.20 eV, particularly preferably 0.005 eV to 0.13 eV, and particularly preferably 0.01 eV to 0.11 eV.

[0162] The oscillator strength of compound (T) is preferably 0.0001 or more, more preferably 0.001 or more, further preferably 0.01 or more, particularly preferably 0.05 or more, and particularly preferably 0.1 or more. The oscillator strength of compound (T) is preferably 1 or less, more preferably 0.8 or less, further preferably 0.6 or less, and particularly preferably 0.3 or less. From the perspective of the excellent external quantum efficiency of the light-emitting element of the present invention, the oscillator strength of compound (T) is preferably 0.0001 or more and 1 or less, more preferably 0.001 or more and 0.8 or less, further preferably 0.01 or more and 0.6 or less, and particularly preferably 0.1 or more and 0.3 or less.

[0163] About ΔE of Compounds ST The density functional method at the B3LYP level was used to optimize the ground state structure of the compound. At this time, 6-31G* was used as the basis function. In addition, Gaussian09 was used as a quantum chemical calculation program to calculate the ΔE of the compound using the time-dependent density functional method at the B3LYP level. ST However, when an atom for which 6-31G* cannot be used is included, LANL2DZ is used for that atom.

[0164] The molecular weight of compound (T) is preferably 1×10 2 ~1×10 4 , more preferably 2×10 2 ~5×10 3 , more preferably 3×10 2 ~3×10 3 , particularly preferably 5×10 2 ~1.5×10 3 .

[0165] From the viewpoint of excellent external quantum efficiency of the light-emitting device of the present invention, the compound (T) is preferably a compound represented by formula (T-1).

[0166] From the viewpoint that the light-emitting element of the present invention has excellent external quantum efficiency, n T1 It is preferably an integer of 0 or more and 3 or less, more preferably an integer of 0 or more and 2 or less, and even more preferably 0 or 1.

[0167] From the viewpoint that the light-emitting element of the present invention has excellent external quantum efficiency, n T2 It is preferably an integer of 1 to 10, more preferably an integer of 1 to 7, further preferably an integer of 1 to 5, and particularly preferably 2 or 3.

[0168] Ar T1represents an aryl group, a substituted amino group or a monovalent heterocyclic group, which may have a substituent. T1 is a substituted amino group, or contains a nitrogen atom having no double bond in the ring and does not contain a group represented by =N- in the ring, a boron atom, -C(=Z T1 )-, a group represented by -S(=O)-, a group represented by -S(=O)2-, and a monovalent heterocyclic group represented by the formula (P).

[0169] As Ar T1 The aryl group represented by the formula (a) includes, for example, a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, a tetracene ring, a fluorene ring, a spirobifluorene ring, an indene ring, a pyrene ring, a perylene ring, A group obtained by removing one hydrogen atom directly bonded to a carbon atom constituting the ring from a ring or a ring formed by condensing these rings, preferably a group selected from a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, a tetracene ring, a fluorene ring, a spirobifluorene ring, an indene ring, a pyrene ring, a perylene ring or The group obtained by removing one hydrogen atom directly bonded to the carbon atom constituting the ring is more preferably phenyl, naphthyl, anthracenyl, phenanthrenyl, dihydrophenanthrenyl, fluorenyl or spirobifluorenyl, further preferably phenyl, naphthyl, fluorenyl or spirobifluorenyl, particularly preferably phenyl, and these groups may have substituents.

[0170] As Ar T1 The monovalent heterocyclic group shown in the formula (I) may be a monovalent donor-type heterocyclic group described below and a monovalent heterocyclic group other than the monovalent donor-type heterocyclic group described below, preferably a carbazole ring, a 9,10-dihydroacridine ring, a 5,10-dihydrophenazine ring, a phenoxazine ring, a phenothiazine ring, an indolocarbazole ring, an indenocarbazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, a naphthyrazine ring, a naphthyrazine ring, an azathane ring, a diazathane ring, a phenanthroline ring, a phenanthroline ring, a dibenzofuran ring, a dibenzothiophene ring, an azacarbazole ring or a diazacarbazole ring. The group obtained by removing one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring from a carbazole ring, an indolocarbazole ring, an indenocarbazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, a dibenzofuran ring or a dibenzothiophene ring, and the group obtained by removing one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring from a carbazole ring, a dibenzofuran ring or a dibenzothiophene ring, and the group obtained by removing one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring from a carbazole ring, a dibenzofuran ring or a dibenzothiophene ring, and these groups optionally have a substituent.

[0171] In Ar T1 In the substituted amino group shown in FIG. 1 , as a substituent possessed by the amino group, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group is preferred, an aryl group or a monovalent heterocyclic group is more preferred, and an aryl group is further preferred, and these groups may further have a substituent. Examples and preferred ranges of the aryl group among the substituents possessed by the amino group are the same as those of Ar T1Examples and preferred ranges of the aryl group shown in . Examples and preferred ranges of the monovalent heterocyclic group among the substituents possessed by the amino group are the same as those of Ar T1 The examples and preferred ranges of the monovalent heterocyclic group are the same as those shown.

[0172] The “nitrogen atom having no double bond” refers to a nitrogen atom having only single bonds between the nitrogen atom and all atoms bonded to the nitrogen atom.

[0173] "Contains a nitrogen atom without a double bond in the ring" means that the ring contains -N(-R N )-(where R N represents a hydrogen atom or a substituent) or a group represented by the following formula.

[0174] [Chemistry 21]

[0175]

[0176] The ring contains a nitrogen atom having no double bond and does not contain a group represented by =N-, a boron atom, -C(=Z) T1 In the monovalent heterocyclic group represented by the formula (P), the number of nitrogen atoms having no double bonds constituting the ring is usually 1 to 10, preferably 1 to 5, more preferably 1 to 3, further preferably 1 or 2, and particularly preferably 1.

[0177] In the monovalent donor-type heterocyclic group, the number of carbon atoms constituting the ring is usually 2 to 60, preferably 5 to 40, and more preferably 10 to 25.

[0178] Examples of the monovalent donor-type heterocyclic group include a pyrrole ring, an indole ring, an isoindole ring, a carbazole ring, a 9,10-dihydroacridine ring, a 5,10-dihydrophenazine ring, an acridone ring, a phenoxazine ring, a phenothiazine ring, an indolocarbazole ring, an indenocarbazole ring, or a ring formed by condensing an aromatic hydrocarbon ring and / or a heterocyclic ring on these heterocyclic rings, wherein one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring is removed, and these groups may have a substituent. Among them, the aromatic hydrocarbon ring optionally condensed on the heterocyclic ring is a ring that does not contain -C(=Z) in the ring described below. T1 The heterocyclic ring optionally fused to the heterocyclic ring is a ring which does not contain a group represented by =N-, a boron atom, -C(=Z)-, or a group represented by =N-. T1 )-, a group represented by -S(=O)-, a group represented by -S(=O)2-, and a heterocyclic ring of a group represented by the above formula (P).

[0179] The monovalent donor heterocyclic group is preferably a group obtained by removing one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring from a pyrrole ring, an indole ring, an isoindole ring, a carbazole ring, a 9,10-dihydroacridine ring, a 5,10-dihydrophenazine ring, an acridone ring, a phenoxazine ring, a phenothiazine ring, an indolocarbazole ring or an indenocarbazole ring, and more preferably a group obtained by removing one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring from a carbazole ring, a 9,10-dihydroacridine ring, a 5,10-dihydrophenazine ring, a phenoxazine ring, a phenothiazine ring, a The group is preferably a group obtained by removing one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring from a carbazole ring, an indolecarbazole ring or an indenocarbazole ring, further preferably a group obtained by removing one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring from a carbazole ring, an indolecarbazole ring or an indenocarbazole ring, and particularly preferably a group obtained by removing one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring from a carbazole ring, and these groups may optionally have a substituent.

[0180] The number of carbon atoms of the monovalent heterocyclic group other than the monovalent donor-type heterocyclic group is usually 2 to 60, preferably 3 to 20, excluding the number of carbon atoms of the substituent.

[0181] Examples of the monovalent heterocyclic group other than the monovalent donor-type heterocyclic group include a diazole ring, a triazole ring, a furan ring, a thiophene ring, an oxadiazole ring, a thiadiazole ring, a pyridine ring, a diazine benzene ring, a triazine ring, a naphthylidene ring, a naphthylidene ring, a triazine ring, an azathane ring, a diazine anthracene ring, a triazine anthracene ring, a phenanthroline ring, a phenanthroline ring, a triazine anthracene ring, a dibenzofuran ring, a dibenzothiophene ring, a dibenzosilylene ring, a dibenzophosphocyclopentadiene ring, an azathane ring, a phenanthroline ring, a phenanthroline ring, a dibenzofuran ring, a dibenzothiophene ring, a dibenzosilylene ring, a dibenzophosphocyclopentadiene ring, a pyridine ... A group obtained by removing one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring from a carbazole ring, a diazacarbazole ring, a ring formed by condensing these heterocycles, and a ring formed by condensing an aromatic hydrocarbon ring to these heterocycles, preferably a group selected from a diazole ring, a triazole ring, a furan ring, a thiophene ring, an oxadiazole ring, a thiadiazole ring, a pyridine ring, a diazine benzene ring, a triazine ring, a naphthylidene ring, a naphthylidene ring, a triazine ring, an azaanthracene ring, a diazanthracene ring, a triazanthracene ring, a phenanthroline ring, a di ... A group obtained by removing one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring from a phenanthrene ring, a triazine ring, a dibenzofuran ring, a dibenzothiophene ring, a dibenzosilylene ring, a dibenzophosphole ring, an azacarbazole ring or a diazacarbazole ring, more preferably a group obtained by removing one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring from a pyridine ring, a diazine benzene ring, a triazine ring, a naphthylidene ring, a naphthylidene ring, an azaanthracene ring, a diazineanthracene ring, a phenanthrene ring, a diazine ring, a dibenzofuran ring, a dibenzothiophene ring, an azacarbazole ring Preferably, the group is a group obtained by removing one or more hydrogen atoms directly bonded to a carbon atom or a heteroatom constituting the ring from a pyridine ring, a diazabenzene ring, a triazine ring, a dibenzofuran ring or a dibenzothiophene ring, and more preferably, the group is a group obtained by removing one hydrogen atom directly bonded to a carbon atom constituting the ring from a dibenzofuran ring or a dibenzothiophene ring, and particularly preferably, the group is a group obtained by removing one hydrogen atom directly bonded to a carbon atom constituting the ring from a dibenzofuran ring or a dibenzothiophene ring, and these groups may have a substituent.

[0182] As Ar T1 The optionally possessed substituent is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkyloxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, a halogen atom or a cyano group, more preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkyloxy group, an aryl group, a monovalent heterocyclic group, a substituted amino group or a cyano group, further preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, particularly preferably an alkyl group, an aryl group or a substituted amino group, and particularly preferably a substituted amino group, and these groups optionally further have a substituent.

[0183] Ar T1 Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group which may be optionally substituted are the same as those of Ar T1 The examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group are the same as those shown.

[0184] As Ar T1The substituent that the optionally possessed substituent further possesses is preferably an alkyl group, cycloalkyl group, alkoxy group, cycloalkyloxy group, aryl group, aryloxy group, monovalent heterocyclic group, substituted amino group, halogen atom or cyano group, more preferably an alkyl group, cycloalkyl group, alkoxy group, cycloalkyloxy group, aryl group, monovalent heterocyclic group or substituted amino group, further preferably an alkyl group, cycloalkyl group, aryl group, monovalent heterocyclic group or substituted amino group, particularly preferably an alkyl group or cycloalkyl group, and these groups may further have substituents.

[0185] Ar T1 Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group which may be further substituted on the substituent group are the same as those of Ar T1 The examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group are the same as those shown.

[0186] From the viewpoint of excellent external quantum efficiency of the light-emitting element of the present invention, at least one Ar T1 It is preferably a monovalent donor-type heterocyclic group, and more preferably a group represented by the formula (T1-1), and these groups may have a substituent.

[0187] That is, the monovalent donor-type heterocyclic group is preferably a group represented by formula (T1-1).

[0188] In Ar T1 When Ar is not a substituted amino group or a monovalent donor-type heterocyclic group, from the viewpoint of excellent external quantum efficiency of the light-emitting device of the present invention, T1 It is preferably an aryl group or a monovalent heterocyclic group other than a monovalent donor-type heterocyclic group, and more preferably an aryl group, and these groups may have a substituent.

[0189] From the viewpoint that the external quantum efficiency of the light-emitting element of the present invention is more excellent, Ar T1 It is preferably an aryl group or a monovalent donor-type heterocyclic group, and more preferably an aryl group or a group represented by the formula (T1-1), and these groups may have a substituent.

[0190] In the presence of multiple Ar T1 In the case of , they may be the same or different and may be directly bonded or bonded via a divalent group to form a ring, but preferably do not form a ring.

[0191] Examples of the "divalent group" include an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, -N(R ArT1 )-, -B(R AeT1 )-, -P(R ArT1 )-, -(O=)P(R ArT1 )-, -Si(R ArT1')2-, a group represented by -S(=O)-, a group represented by -S(=O)2, a group represented by -C(=Z T1 )-, an oxygen atom or a sulfur atom, preferably an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, -N(R ArT1 )-, -P(R ArT1 )-, -Si(R ArT1 ')2-, an oxygen atom or a sulfur atom, more preferably an alkylene group, a cycloalkylene group, -N(R ArT1 )-, -P(R ArT1 )-, -Si(R ArT1 ')2-, an oxygen atom or a sulfur atom, and more preferably an alkylene group, -N(R ArT1 )-, an oxygen atom or a sulfur atom, particularly preferably an oxygen atom or a sulfur atom, and these groups may have a substituent.

[0192] Examples and preferred ranges of the substituents that the divalent group may optionally have are similar to those of Ar T1 Examples and preferred ranges of the substituents which may be optionally possessed are the same.

[0193] Examples and preferred ranges of the substituents that the divalent group may further have are similar to those of Ar. T1 Examples and preferred ranges of substituents that may be further possessed on the substituents that may be possessed are the same as those of the substituents that may be further possessed.

[0194] Examples and preferred ranges of the alkylene group in the divalent group are the same as those of L described below. A Examples and preferred ranges of the alkylene group are the same as those of L described below. A The examples and preferred ranges of the cycloalkylene group are the same as those shown.

[0195] Examples and preferred ranges of the arylene group in the divalent group are the same as those of L described below. T1 Examples and preferred ranges of the arylene group are the same as those of L described below. Examples and preferred ranges of the divalent heterocyclic group in the divalent group are the same as those of L described below. T1 The examples and preferred ranges of the divalent heterocyclic group are the same as those shown above.

[0196] R ArT1 and R ArT1 ' each independently represents 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, a halogen atom or a cyano group, and these groups may have a substituent.

[0197] R ArT1 Examples and preferred ranges of R are described below. XT1The examples and preferred ranges are the same.

[0198] R ArT1 Examples and preferred ranges of ' are the same as those described below. XT1 The examples and preferred ranges of ' are the same.

[0199] ·Group represented by formula (T1-1)

[0200] "The ring does not contain -C (=Z T1 The number of carbon atoms of the "aromatic hydrocarbon ring of the group represented by )-" excluding the number of carbon atoms of the substituent is usually 6 to 60, preferably 6 to 30, more preferably 6 to 18.

[0201] As the ring does not contain -C (=Z T1 )-, for example, a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, a tetracene ring, a fluorene ring, a spirobifluorene ring, an indene ring, a pyrene ring, a perylene ring, The ring and the ring formed by condensing these rings are preferably a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, a tetracene ring, a fluorene ring, a spirobifluorene ring, an indene ring, a pyrene ring, a perylene ring or The ring is more preferably a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, a fluorene ring or a spirobifluorene ring, further preferably a benzene ring, a naphthalene ring, a fluorene ring or a spirobifluorene ring, particularly preferably a benzene ring or a fluorene ring, and particularly preferably a benzene ring, and these rings may have a substituent.

[0202] "The ring does not contain a group represented by =N-, a boron atom, -C(=Z T1 The number of carbon atoms of the "heterocyclic ring" excluding the number of carbon atoms of the substituent is usually 2 to 60, preferably 3 to 30, and more preferably 4 to 15.

[0203] As the group represented by =N-, boron atom, -C(=Z) not contained in the ring T1 The heterocyclic ring of the group represented by the formula (P) may include a pyrrole ring, a furan ring, a thiophene ring, a silole ring, a phosphole ring, an indole ring, a benzofuran ring, a benzothiophene ring, a benzosilole ring, a benzophosphole ring, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, a dibenzosilole ring, a dibenzophosphole ring, a phenoxazine ring, a phenothiazine ring, a 9,10-dihydroacridine ring, a 5,10-dihydrophenazine ring, a ring formed by condensing these rings, and a ring formed by condensing these rings with a ring not containing -C(=Z) in the ring. T1)-, preferably a pyrrole ring, a furan ring, a thiophene ring, a silolene ring, a phosphole ring, an indole ring, a benzofuran ring, a benzothiophene ring, a benzosilolene ring, a benzophosphole ring, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, a dibenzosilolene ring, a dibenzophosphole ring, a phenoxazine ring, a phenothiazine ring, a 9,10-dihydroacridine ring or a 5,10-dihydrophenazine ring, more preferably an indole ring. Preferably, the ring is a benzofuran ring, a benzothiophene ring, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, a phenoxazine ring, a phenothiazine ring, a 9,10-dihydroacridine ring or a 5,10-dihydrophenazine ring, more preferably a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, a phenoxazine ring, a phenothiazine ring, a 9,10-dihydroacridine ring or a 5,10-dihydrophenazine ring, particularly preferably a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, and especially preferably a carbazole ring, and these rings optionally have substituents.

[0204] Ring R T1 and Ring R T2 Examples and preferred ranges of the optional substituents are similar to those of Ar T1 Examples and preferred ranges of the substituents which may be optionally possessed are the same.

[0205] Ring R T1 and Ring R T2 Examples and preferred ranges of the substituents optionally further possessed by the substituents are similar to those of Ar T1 Examples and preferred ranges of substituents that may be further possessed on the substituents that may be possessed are the same as those of the substituents that may be further possessed.

[0206] Ring R T1 and Ring R T2 At least one of them preferably does not contain -C(=Z T1 )- is an aromatic hydrocarbon ring, more preferably a benzene ring, and these rings may have a substituent.

[0207] Ring R T1 and Ring R T2 Both preferably do not contain -C (=Z T1 )- is an aromatic hydrocarbon ring, more preferably a benzene ring, and these rings may have a substituent.

[0208] X T1 Preferably, it is a single bond, an oxygen atom, a sulfur atom or -C(R XT1 The group represented by ')2- is more preferably a single bond, an oxygen atom or a sulfur atom, and further preferably a single bond.

[0209] R XT1It is preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, more preferably an aryl group or a monovalent heterocyclic group, and further preferably an aryl group, and these groups may have a substituent.

[0210] R XT1 ' is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an alkyl group, a cycloalkyl group or an aryl group, further preferably an alkyl group or a cycloalkyl group, and these groups may have a substituent.

[0211] The existence of multiple R XT1 ' are optionally the same or different, and optionally bonded to each other and form a ring together with the carbon atom to which each is bonded, but preferably do not form a ring.

[0212] R XT1 and R XT1 Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group represented by ' are the same as those of Ar T1 The examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group are the same as those shown.

[0213] R XT1 and R XT1 Examples and preferred ranges of the optional substituents are similar to those of Ar T1 Examples and preferred ranges of substituents that may be further possessed on the substituents that may be possessed are the same as those of the substituents that may be further possessed.

[0214] R XT1 and Ring R T1 The optional substituents, R XT1 and Ring RT 2 The optional substituents, R XT1 ′ and ring R T1 The optional substituents, and R XT1 ' and ring R1 2 The substituents optionally possessed may each be bonded directly or via a divalent group and may form a ring together with the atoms to which they are bonded, but preferably do not form a ring.

[0215] The group represented by formula (T1-1) is preferably a group represented by formula (T1-1A), a group represented by formula (T1-1B), a group represented by formula (T1-1C) or a group represented by formula (T1-1D), more preferably a group represented by formula (T1-1A), a group represented by formula (T1-1B) or a group represented by formula (T1-1C), and further preferably a group represented by formula (T1-1A).

[0216] X T2 and X T3 Preferably, a single bond, -N(R XT2 )- or -C(R XT2')2-, more preferably a single bond or -C(R XT2 ') The group shown in 2-.

[0217] X T2 and X T3 At least one of X is preferably a single bond, more preferably X T3 For a single key.

[0218] In X T2 and X T3 When at least one of them is a single bond, the other is preferably an oxygen atom, a sulfur atom, -N(R XT2 )- or -C(R XT2 ')2-, more preferably -N(R XT2 ) - The group shown or -C(R XT2 ')2-, more preferably -C(R XT2 ') The group shown in 2-.

[0219] R XT2 Examples and preferred ranges of R XT1 The examples and preferred ranges are the same.

[0220] R XT2 Examples and preferred ranges of ' and R XT1 The examples and preferred ranges of ' are the same.

[0221] R XT2 and R XT2 Examples and preferred ranges of the optional substituents are similar to those of R XT1 and R XT1 Examples and preferred ranges of the substituents that may be optionally possessed are the same as those of '.

[0222] R T1 , R T2 , R T3 , R T4 , R T5 , R T6 , R T7 , R T8 , R T9 , R T10 , R T11 and R T12 Preferred are hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkyloxy group, aryl group, monovalent heterocyclic group, substituted amino group or cyano group, more preferred are hydrogen atom, alkyl group, cycloalkyl group, aryl group, monovalent heterocyclic group or substituted amino group, and these groups may further have a substituent.

[0223] In the group represented by formula (T1-1A), R T1 , RT2 , R T4 , R T5 , R T7 and R T8 It is preferably a hydrogen atom, an alkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, more preferably a hydrogen atom or an alkyl group, and still more preferably a hydrogen atom, and these groups may further have a substituent.

[0224] In the group represented by formula (T1-1A), R T3 and R T6 It is preferably an alkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, more preferably an aryl group, a monovalent heterocyclic group or a substituted amino group, and still more preferably a substituted amino group, and these groups may further have a substituent.

[0225] In the formula (T1 - 1B), (T1-1C) and (T1-1D), R T1 , R T2 , R T3 , R T4 , R T5 , R T6 , R T7 , R T8 , R T9 , R T10 , R T11 and RT 12 It is preferably a hydrogen atom, an alkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, more preferably a hydrogen atom or an alkyl group, and still more preferably a hydrogen atom, and these groups may further have a substituent.

[0226] R T1 , R T2 , R T3 , R T4 , R T5 , R T6 , R T7 , R T8 , R T9 , R T10 , R T11 and R T12 Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group shown are the same as those of Ar T1 The examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group are the same as those shown.

[0227] R T1 , R T2 , R T3 , R T4 , R T5 , R T6 , R T7 , R T8 , RT9 , R T10 , R T11 and R T12 Examples and preferred ranges of the optional substituents are similar to those of Ar T1 Examples and preferred ranges of substituents that may be further possessed on the substituents that may be possessed are the same as those of the substituents that may be further possessed.

[0228] R T1 With R T2 , R T2 With R T3 , R T3 With R T4 , R T5 With R T6 , R T6 With R T7 , R T7 With R T8 , R T9 With R T10 , R T10 With R T11 , and R T11 With R T12 They are optionally bonded directly or via a divalent group and form a ring together with the carbon atom to which they are bonded, but preferably do not form a ring.

[0229] L T1 represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, -N(R T1 ')-, an oxygen atom or a sulfur atom, and these groups may have a substituent.

[0230] L T1 It is preferably an alkylene group, a cycloalkylene group, an arylene group or a divalent heterocyclic group, more preferably an arylene group or a divalent heterocyclic group, and further preferably an arylene group, and these groups may have a substituent.

[0231] As L T1 The arylene group shown is preferably a phenylene group, a naphthalene diyl group, a fluorene diyl group, a phenanthrene diyl group or a dihydrophenanthrene diyl group, more preferably a group shown by formula (A-1) to formula (A-9), formula (A-19) or formula (A-20), further preferably a group shown by formula (A-1) to formula (A-3), particularly preferably a group shown by formula (A-1) or (A-2), and especially preferably a group shown by formula (A-1), and these groups optionally have substituents.

[0232] As L T1The divalent heterocyclic group represented is preferably a group represented by formula (AA-1) to formula (AA-34), more preferably a group represented by formula (AA-1) to formula (AA-6), formula (AA-10) to formula (AA-21) or formula (AA-24) to formula (AA-34), further preferably a group represented by formula (AA-1) to formula (AA-4), formula (AA-10) to formula (AA-15) or formula (AA-29) to formula (AA-34), particularly preferably a group represented by formula (AA-2), formula (AA-4), formula (AA-10), formula (AA-12) or formula (AA-14).

[0233] L T1 Examples and preferred ranges of the optional substituents are similar to those of Ar T1 Examples and preferred ranges of the substituents which may be optionally possessed are the same.

[0234] L T1 Examples and preferred ranges of the substituents optionally further possessed by the substituents are similar to those of Ar T1 Examples and preferred ranges of substituents that may be further possessed on the substituents that may be possessed are the same as those of the substituents that may be further possessed.

[0235] R T1 ' is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups may have a substituent.

[0236] R T1 Examples and preferred ranges of the aryl group and the monovalent heterocyclic group represented by ' are the same as those of Ar T1 The examples and preferred ranges of the aryl group and the monovalent heterocyclic group are the same as those shown.

[0237] R T1 Examples and preferred ranges of the optional substituents are similar to those of Ar T1 Examples and preferred ranges of substituents that may be further possessed on the substituents that may be possessed are the same as those of the substituents that may be further possessed.

[0238] In the presence of multiple L T1 In the case of , they may be the same or different and may be directly bonded or bonded via a divalent group to form a ring, but preferably do not form a ring.

[0239] Ar T2 is a boron atom, -C(=Z T1 )-, a group represented by -S(=O)-, a group represented by -S(=O)2-, a group represented by the above formula (P), an aromatic hydrocarbon group having an electron-withdrawing group, or a heterocyclic group containing a group represented by =N- in the ring, and these groups optionally have substituents.

[0240] From the viewpoint that the light-emitting element of the present invention has excellent external quantum efficiency, Ar T2 Preferably, a boron atom, -C(=Z T1 )-, a group represented by -S(=O)2, a group represented by the above formula (P), an aromatic hydrocarbon group having an electron-withdrawing group, or a heterocyclic group containing a group represented by =N- in the ring, more preferably a boron atom, -C(=Z T1 )-, a group represented by -S(=O)2, an aromatic hydrocarbon group having an electron-withdrawing group, or a heterocyclic group containing a group represented by =N- in the ring, further preferably a group represented by -S(=O)2, an aromatic hydrocarbon group having an electron-withdrawing group, or a heterocyclic group containing a group represented by =N- in the ring, particularly preferably an aromatic hydrocarbon group having an electron-withdrawing group, or a heterocyclic group containing a group represented by =N- in the ring, especially preferably a heterocyclic group containing a group represented by =N- in the ring, and these groups optionally have substituents.

[0241] Z T1 Preferred is an oxygen atom.

[0242] R ZT1 An alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group is preferred, an aryl group or a monovalent heterocyclic group is more preferred, and an aryl group is further preferred. These groups may have a substituent.

[0243] R T1 Examples and preferred ranges of the aryl group and the monovalent heterocyclic group shown are the same as those of Ar T1 The examples and preferred ranges of the aryl group and the monovalent heterocyclic group are the same as those shown.

[0244] R T1 Examples and preferred ranges of the optional substituents are similar to those of Ar T1 Examples and preferred ranges of substituents that may be further possessed on the substituents that may be possessed are the same as those of the substituents that may be further possessed.

[0245] In the aromatic hydrocarbon group having an electron-withdrawing group, the number of carbon atoms of the aromatic hydrocarbon group excluding the number of carbon atoms of the substituent is usually 6 to 60, preferably 6 to 30, more preferably 6 to 18.

[0246] Examples of the aromatic hydrocarbon group having an electron-withdrawing group include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, a tetracene ring, a fluorene ring, a spirobifluorene ring, an indene ring, a pyrene ring, a perylene ring, The group obtained by removing one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring from the ring and the ring formed by condensing these rings is preferably a group selected from a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, a tetracene ring, a fluorene ring, a spirobifluorene ring, an indene ring, a pyrene ring, a perylene ring or The group obtained by removing one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring from the ring is more preferably a group obtained by removing one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring from a benzene ring, a naphthalene ring, anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, a fluorene ring or a spirobifluorene ring, further preferably a group obtained by removing one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring from a benzene ring, a naphthalene ring, a fluorene ring or a spirobifluorene ring, particularly preferably a group obtained by removing one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring from a benzene ring or a fluorene ring, and particularly preferably a group obtained by removing one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring from a benzene ring, and these groups may have a substituent.

[0247] Examples of the electron withdrawing group include an alkyl group having a fluorine atom as a substituent, a fluorine atom, a cyano group, and a nitro group. An alkyl group having a fluorine atom as a substituent, a fluorine atom, or a cyano group is preferred, and a cyano group is more preferred.

[0248] As the alkyl group having a fluorine atom as a substituent, a trifluoromethyl group, a pentafluoroethyl group, a perfluorobutyl group, a perfluorohexyl group, and a perfluorooctyl group are preferred.

[0249] In the aromatic hydrocarbon group having an electron-withdrawing group, the number of electron-withdrawing groups possessed by the aromatic hydrocarbon group is usually 1 to 10, preferably 1 to 5, more preferably 1 to 3, and further preferably 1 or 2.

[0250] In the heterocyclic group containing a group represented by =N- in the ring, the number of nitrogen atoms having double bonds constituting the ring is usually 1 to 10, preferably 1 to 7, more preferably 1 to 5, further preferably 1 to 3, particularly preferably 3.

[0251] In the heterocyclic group containing a group represented by =N- in the ring, the number of carbon atoms constituting the ring is usually 1 to 60, preferably 2 to 30, more preferably 3 to 15, particularly preferably 3 to 5.

[0252] Examples of the heterocyclic group containing a group represented by =N- in the ring include a diazole ring, a triazole ring, an oxadiazole ring, a thiadiazole ring, a thiazole ring, an oxazole ring, an isothiazole ring, an isoxazole ring, a benzodiazole ring, a benzotriazole ring, a benzoxadiazole ring, a benzothiadiazole ring, a benzothiazole ring, a benzoxazole ring, an azacarbazole ring, a diazacarbazole ring, a pyridine ring, a diazobenzene ring, a triazine ring, a naphthalene ring, a diazonaphthalene ring, a triazonaphthalene ring, a tetraazonaphthalene ring, an azaanthracene ring, a diazonaphthalene ring, a triazonaphthalene ring, a tetraazonaphthalene ring, an azaphenanthracene ring, a diazonaphthalene ring, a triazonaphthalene ring, a tetraazonaphthalene ring, an azaphenanthracene ring, a diazonaphthalene ring, a triazonaphthalene ring, a tetraazonaphthalene ring, an azaphenanthracene ring, a diazonaphthalene ring, a triazonaphthalene ring, a tetraazonaphthalene ring, or an aromatic ring condensed on these heterocyclic rings. The aromatic ring is obtained by removing one or more hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring, and is preferably selected from the group consisting of a diazole ring, a triazole ring, an oxadiazole ring, a thiadiazole ring, a thiazole ring, an oxazole ring, an isothiazole ring, an isoxazole ring, a benzodiazole ring, a benzotriazole ring, a benzoxadiazole ring, a benzothiadiazole ring, a benzothiazole ring, a benzoxazole ring, an azacarbazole ring, a diazacarbazole ring, a pyridine ring, a diazobenzene ring, a triazine ring, a naphthalene ring, a diazonaphthene ring, a triazonaphthene ring, a tetraazonaphthene ring, an azaanthracene ring, a diazonaphthene ring, a triazonaphthene ring, a tetraazonaphthene ring, an azaphenanthroline ring, a diazonaphthene ring, a triazonaphthene ring, a tetraazonaphthene ring, an azaphenanthroline ring, a diazonaphthene ring, a triazonaphthene ring, a tetraazonaphthene ring The group obtained by removing one or more hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring from the ring, more preferably a group obtained by removing one or more hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring from a triazole ring, an oxadiazole ring, a thiadiazole ring, an azacarbazole ring, a diazacarbazole ring, a pyridine ring, a diazobenzene ring, a triazine ring, a naphthalene ring, a diazobenzene ring, a triazobenzene ring, a tetraazobenzene ring, an azaanthracene ring, a diazobenzene ring, a triazobenzene ring, a tetraazobenzene ring, an azaphenanthracene ring, a diazobenzene ring, a triazobenzene ring, a tetraazobenzene ring, an azaphenanthracene ring, a diazobenzene ring, a triazobenzene ring or a tetraazobenzene ring, and more preferably a group obtained by removing one or more hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring from a triazole ring, an oxadiazole ring, a thiadiazole ring, a pyridine ring, a diazobenzene ring, a triazobenzene ring or a tetraazobenzene ring. Preferably, the group is a group obtained by removing one or more hydrogen atoms directly bonded to a carbon atom or a heteroatom constituting the ring from a pyridine ring, a diazine ring, a triazine ring, a naphthyl ring, a naphthyl ring, an azathane ring, a diazine ring, a phenanthroline ring or a diazine ring, and is particularly preferably a group obtained by removing one or more hydrogen atoms directly bonded to a carbon atom constituting the ring from a pyridine ring, a diazine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, an acridine ring, a phenazine ring or a phenanthroline ring, and is particularly preferably a group obtained by removing one or more hydrogen atoms directly bonded to a carbon atom constituting the ring from a pyridine ring, a diazine ring or a triazine ring, and these groups may have a substituent.

[0253] As Ar T2 The optionally possessed substituent (different from the group represented by the formula (1T') described later. The same applies hereinafter) is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkyloxy group, a halogen atom or a cyano group, more preferably an alkyl group, a cycloalkyl group, a fluorine atom or a cyano group, and further preferably an alkyl group or a cycloalkyl group, and these groups optionally have a substituent.

[0254] Ar T2 Examples and preferred ranges of the substituents optionally further possessed by the substituents are similar to those of Ar T1 Examples and preferred ranges of substituents that may be further possessed on the substituents that may be possessed are the same as those of the substituents that may be further possessed.

[0255] Ar T1 With L T1 Preferably, Ar is not directly bonded or is bonded via a divalent group to form a ring. T2 With L T1 Preferably, Ar is not directly bonded or is bonded via a divalent group to form a ring. T1 with Ar T2 It is preferred that the two groups not be directly bonded or bonded via a divalent group to form a ring.

[0256] In the compound represented by formula (T-1), Ar T2 In the case of a heterocyclic group containing a group represented by =N- in the ring, from the perspective of excellent external quantum efficiency of the light-emitting element of the present invention, the compound represented by formula (T-1) is preferably a compound represented by formula (T'-1) to formula (T'-14), more preferably a compound represented by formula (T'-1) to formula (T'-8) or formula (T'-12) to formula (T'-14), further preferably a compound represented by formula (T'-1) to formula (T'-4) or formula (T'-12) to formula (T'-14), particularly preferably a compound represented by formula (T'-1) to formula (T'-4), and particularly preferably a compound represented by formula (T'-4).

[0257] In the compound represented by formula (T-1), Ar T2 In the case of an aromatic hydrocarbon group having an electron-withdrawing group, from the perspective of excellent external quantum efficiency of the light-emitting element of the present invention, the compound represented by formula (T-1) is preferably a compound represented by formula (T'-15) to formula (T'-18), more preferably a compound represented by formula (T'-15), formula (T'-17) or formula (T'-18), and further preferably a compound represented by formula (T'-15).

[0258] In the compound represented by formula (T-1), Ar T2 is a boron atom, -C(=Z T1)-, a group represented by -S(=O)-, a group represented by -S(=O)2-, or a group represented by the above-mentioned formula (P), from the perspective of excellent external quantum efficiency of the light-emitting element of the present invention, the compound represented by formula (T-1) is preferably a compound represented by formula (T'-18) to formula (T'-22), more preferably a compound represented by formula (T'-19) to formula (T'-22), further preferably a compound represented by formula (T'-20) or formula (T'-21), and particularly preferably a compound represented by formula (T'-21).

[0259] From the perspective of better external quantum efficiency of the light-emitting element of the present invention, the compound represented by formula (T-1) is preferably a compound represented by formula (T'-1) to formula (T'-4), formula (T'-12) to formula (T'-14), formula (T'-15), formula (T'-17), formula (T'-18), formula (T'-20) or formula (T'-21), more preferably a compound represented by formula (T'-1) to formula (T'-4), formula (T'-15) or formula (T'-21), further preferably a compound represented by formula (T'-1) to formula (T'-4), and particularly preferably a compound represented by formula (T'-4).

[0260] From the perspective that the values ​​of x and y of the CIE chromaticity coordinates of the light-emitting element of the present invention become smaller (for example, the x of the chromaticity coordinates is less than 0.25, and the y of the chromaticity coordinates is less than 0.45) and the external quantum efficiency of the light-emitting element of the present invention is better, the compound represented by formula (T-1) is preferably a compound represented by formula (T'-1) to formula (T'-4) or formula (T'-19) to formula (T'-22), more preferably a compound represented by formula (T'-4) or formula (T'-19) to formula (T'-21), and further preferably a compound represented by formula (T'-19).

[0261] [Chemistry 22]

[0262]

[0263] [Chemistry 23]

[0264]

[0265] [Chemistry 24]

[0266]

[0267] [Chemistry 25]

[0268]

[0269] [Chemistry 26]

[0270]

[0271] [Chemistry 27]

[0272]

[0273] [Wherein,

[0274] R 1T represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a halogen atom, a cyano group or a group represented by the formula (1T'), and these groups may have a substituent. 1T are optionally the same or different, and optionally directly bonded or bonded via a divalent group to form a ring. 1T At least one of them is a group represented by formula (1T').

[0275] R 1T ' represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an electron withdrawing group or a group represented by the formula (1T'), and these groups may have a substituent. 1T ' are optionally the same or different, and optionally directly bonded or bonded via a divalent group to form a ring. 1T At least one of ' is a group represented by formula (1T'), and at least one is an electron-withdrawing group.]

[0276] The existence of multiple R 1T 1 or 2 R's 1T Preferred is a group represented by formula (1T').

[0277] The existence of multiple R 1T 1 or 2 R in ' 1T ' is preferably a group represented by the formula (1T').

[0278] The existence of multiple R 1T 1 to 5 R in ' 1T ' is preferably an electron-withdrawing group, more preferably 1 to 3 R 1T ' is an electron-withdrawing group, preferably one or two R 1T ' is an electron withdrawing group.

[0279] [Chemistry 28]

[0280]

[0281] [Wherein, L T1 、n T1 and Ar T1 Means the same as above.]

[0282] R 1TIt is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkyloxy group, a fluorine atom, a cyano group or a group represented by the formula (1T'), more preferably a hydrogen atom, an alkyl group, a cycloalkyl group or a group represented by the formula (1T'), further preferably a hydrogen atom, an alkyl group or a group represented by the formula (1T'), particularly preferably a hydrogen atom or a group represented by the formula (1T'), and these groups optionally have substituents.

[0283] R 1T ' is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkyloxy group, an electron-withdrawing group or a group represented by the formula (1T'), more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an electron-withdrawing group or a group represented by the formula (1T'), further preferably a hydrogen atom, an alkyl group, an electron-withdrawing group or a group represented by the formula (1T'), particularly preferably a hydrogen atom, an electron-withdrawing group or a group represented by the formula (1T'), and these groups optionally have substituents.

[0284] R 1T and R 1T Examples and preferred ranges of the optional substituents are similar to those of Ar T1 Examples and preferred ranges of substituents that may be further possessed on the substituents that may be possessed are the same as those of the substituents that may be further possessed.

[0285] Examples of the compound (T) include compounds represented by the following formula. 1 represents a group represented by -N= or a group represented by -CH=. 2 represents an oxygen atom or a sulfur atom. 1 and Z 2 They may be the same or different.

[0286] [Chemistry 291

[0287]

[0288] [Chemistry 30]

[0289]

[0290] [Chemistry 31]

[0291]

[0292] [Chemistry 32]

[0293]

[0294] [Chemistry 33]

[0295]

[0296] [Chemistry 34]

[0297]

[0298] [Chemistry 35]

[0299]

[0300] [Chemistry 36]

[0301]

[0302] [Chemistry 37]

[0303]

[0304] [Chemistry 38]

[0305]

[0306] [Chemistry 39]

[0307]

[0308] [Chemistry 40]

[0309]

[0310] [Chemistry 41]

[0311]

[0312] [Chemistry 42]

[0313]

[0314] [Chemistry 43]

[0315]

[0316] [Chemistry 44]

[0317]

[0318] [Chemistry 45]

[0319]

[0320] [Chemistry 46]

[0321]

[0322] [Chemistry 47]

[0323]

[0324] [Chemistry 48]

[0325]

[0326] [Chemistry 49]

[0327]

[0328] [Chemistry 50]

[0329]

[0330] [Chemistry 51]

[0331]

[0332] [Chemistry 52]

[0333]

[0334] [Chemistry 53]

[0335]

[0336] [Chemistry 54]

[0337]

[0338] Z 1 It is preferably a group represented by -N=. 2 Preferred is an oxygen atom.

[0339] Compound (T) can be obtained from Aldrich, Luminescence Technology Corp., etc. In addition, it can be synthesized according to the method described in, for example, International Publication No. 2007 / 063754, International Publication No. 2008 / 056746, International Publication No. 2011 / 032686, International Publication No. 2012 / 096263, Japanese Patent Application Publication No. 2009-227663, Japanese Patent Application Publication No. 2010-275255, Advanced Materials (Adv. Mater), Vol. 26, pp. 7931-7958, 2014.

[0340] [Main material]

[0341] From the viewpoint of excellent external quantum efficiency of the light-emitting element of the present invention, the first organic layer is preferably a layer containing compound (T) and a host material having at least one function of hole injection property, hole transport property, electron injection property and electron transport property.

[0342] The host material is classified into low molecular weight compounds and high molecular weight compounds, and is preferably a high molecular weight compound, and more preferably a high molecular weight compound including a structural unit represented by formula (Y).

[0343] In other words, from the perspective of achieving a better external quantum efficiency of the light-emitting element of the present invention, the first organic layer is preferably a layer containing a composition comprising compound (T) and a polymer compound containing a structural unit represented by formula (Y) and containing no phosphorescent metal complex.

[0344] When the first organic layer is a layer containing the compound (T) and a host material, the host material may contain one type alone or two or more types. However, the compound (T) is different from the host material.

[0345] When the first organic layer is a layer containing the compound (T) and a host material, the compound (T) is preferably a light-emitting material.

[0346] The host material refers to a material that is responsible for transferring electrical energy to the luminescent material. By effectively transferring electrical energy from the host material to the luminescent material, the luminescent material can emit light more efficiently. Therefore, it is preferred that the lowest excited triplet state of the host material is at a higher energy level than the lowest excited triplet state of the luminescent material, and the lowest excited singlet state of the host material is at a higher energy level than the lowest excited singlet state of the luminescent material.

[0347] When the first organic layer is a layer containing a compound (T) and a main material, the content of the compound (T) is generally 0.1 to 50 parts by mass, preferably 1 to 45 parts by mass, more preferably 5 to 40 parts by mass, and further preferably 10 to 20 parts by mass, when the total of the compound (T) and the main material is set to 100 parts by mass.

[0348] In order to produce the light-emitting device of the present invention by a solution coating process, the host material is preferably a host material that is soluble in a solvent that can dissolve the compound (T) contained in the first organic layer.

[0349] [Low molecular weight entities]

[0350] The low molecular weight compound (hereinafter referred to as "low molecular weight host") preferred as the host material is preferably a compound represented by formula (H-1) or a compound represented by formula (H-2), and more preferably a compound represented by formula (H-1). However, the compound represented by formula (H-1) and the compound represented by formula (H-2) are different from compound (T). The compound represented by formula (H-1) is different from the compound represented by formula (H-2).

[0351] [Chemistry 55]

[0352]

[0353] [Wherein,

[0354] n H1It represents an integer greater than or equal to 0 and less than or equal to 10.

[0355] Ar H1 and Ar H2 Each independently represents a ring that does not contain -C (=Z T1 )-, or a group obtained by removing one hydrogen atom directly bonded to a carbon atom constituting the ring from an aromatic hydrocarbon ring of a group represented by =N-, a boron atom, -C(=Z T1 )-, a group represented by -S(=O)-, a group represented by -S(=O)2-, and a group obtained by removing one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring from the heterocyclic ring of the group represented by the above formula (P) (the group optionally has a substituent).

[0356] L H1 is an alkylene group which may have a substituent or a cycloalkylene group which may have a substituent, or is a group which does not contain -C(=Z) in the ring. T1 )-, which is a group obtained by removing two hydrogen atoms directly bonded to the carbon atoms constituting the ring from the aromatic hydrocarbon ring of the group represented by =N- (the group may have a substituent other than an electron withdrawing group), or a group not including a group represented by =N-, a boron atom, -C(=Z) in the ring T1 )-, -S(=O)-, -S(=O)2-, and the group obtained by removing two hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring from the heterocyclic ring of the group represented by the above formula (P) (the group may have a substituent). H1 In the case of , they are optionally the same or different.

[0357] Z T1 Means the same as above.]

[0358] n H1 It is preferably an integer of 0 to 5, more preferably an integer of 0 to 3, further preferably 1 or 2, and particularly preferably 1.

[0359] Ar H1 and Ar H2 Preferably, the ring is selected from a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, a tetracene ring, a fluorene ring, a spirobifluorene ring, an indene ring, a pyrene ring, a perylene ring, A group obtained by removing one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring from a ring formed by condensing these rings, and more preferably a ... A group obtained by removing one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring from a pyrrole ring, a furan ring, a thiophene ring, a silole ring, a phosphole ring, an indole ring, a benzofuran ring, a benzothiophene ring, a benzosilole ring, a benzophosphole ring, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, a dibenzosilole ring, a dibenzophosphole ring, a phenoxazine ring, a phenothiazine ring, a 9,10-dihydroacridine ring or a 5,10-dihydrophenazine ring, and more preferably a group obtained by removing one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring from a benzene ring, a fluorene ring, a spirobifluorene ring, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, a dibenzosilole ring, a dibenzophosphole ring, a phenoxazine ring, a phenothiazine ring, a 9,10-dihydroacridine ring or a 5,10-dihydrophenazine ring, and more preferably a group obtained by removing one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring from a benzene ring, a fluorene ring, a spirobifluorene ring, a carbazole ring, a dibenzofuran ring, The group obtained by removing one hydrogen atom directly bonded to a carbon atom or heteroatom constituting the ring from a dibenzothiophene ring, a phenoxazine ring, a phenothiazine ring, a 9,10-dihydroacridine ring or a 5,10-dihydrophenazine ring is particularly preferably a group obtained by removing one hydrogen atom directly bonded to a carbon atom or heteroatom constituting the ring from a benzene ring, a fluorene ring, a spirobifluorene ring, a carbazole ring, a dibenzofuran ring or a dibenzothiophene ring is particularly preferably a group obtained by removing one hydrogen atom directly bonded to a carbon atom or heteroatom constituting the ring from a carbazole ring, a dibenzofuran ring or a dibenzothiophene ring, and these groups optionally have substituents.

[0360] L H1 Preferably, the ring is selected from a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, a tetracene ring, a fluorene ring, a spirobifluorene ring, an indene ring, a pyrene ring, a perylene ring, A group obtained by removing two hydrogen atoms directly bonded to a carbon atom or a heteroatom constituting the ring from a ring formed by condensing these rings, and more preferably a ... A group obtained by removing two hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring from a pyrrole ring, a furan ring, a thiophene ring, a silole ring, a phosphole ring, an indole ring, a benzofuran ring, a benzothiophene ring, a benzosilole ring, a benzophosphole ring, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, a dibenzosilole ring, a dibenzophosphole ring, a phenoxazine ring, a phenothiazine ring, a 9,10-dihydroacridine ring or a 5,10-dihydrophenazine ring, and more preferably a group obtained by removing two hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring from a benzene ring, a fluorene ring, a spirobifluorene ring, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, a dibenzosilole ring, a dibenzophosphole ring, a phenoxazine ring, a phenothiazine ring, a 9,10-dihydroacridine ring or a 5,10-dihydrophenazine ring, and more preferably a group obtained by removing two hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring from a benzene ring, a fluorene ring, a spirobifluorene ring, a carbazole ring, a dibenzofuran ring, The group obtained by removing two hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring from a dibenzothiophene ring, a phenoxazine ring, a phenothiazine ring, a 9,10-dihydroacridine ring or a 5,10-dihydrophenazine ring is particularly preferably a group obtained by removing two hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring from a benzene ring, a fluorene ring, a spirobifluorene ring, a carbazole ring, a dibenzofuran ring or a dibenzothiophene ring is particularly preferably a group obtained by removing two hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring from a carbazole ring, a dibenzofuran ring or a dibenzothiophene ring, and these groups optionally have substituents.

[0361] As Ar H1 ,Ar H2 and L H1 The optional substituent is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkyloxy group, an aryl group, a monovalent heterocyclic 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, further preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, particularly preferably an alkyl group or a cycloalkyl group, and these groups may further have a substituent.

[0362] However, Ar H1 ,Ar H2 and L H1 The aryl group in the optional substituent is a substituent having no -C(=Z) in the ring. T1 A group obtained by removing one hydrogen atom directly bonded to a carbon atom constituting the ring from the aromatic hydrocarbon ring of the group represented by - (the group may have a substituent other than an electron withdrawing group). H1 ,Ar H2 and L H1 The monovalent heterocyclic group in the optional substituent is a group not including a group represented by =N-, a boron atom, -C(=Z) in the ring. T1 )-, a group represented by -S(=O)-, a group represented by -S(=O)2-, and a group obtained by removing one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring from the heterocyclic ring of the group represented by the above formula (P) (the group optionally has a substituent).

[0363] As Ar H1 ,ArH2 and L H1 The substituent that may be further possessed on the substituent that may be possessed is preferably an alkyl group, a cycloalkyl group, an alkoxy group or a cycloalkoxy group, and more preferably an alkyl group or a cycloalkyl group.

[0364] [Chemistry 56]

[0365]

[0366] [Wherein,

[0367] n H2 It represents an integer greater than or equal to 1 and less than or equal to 10.

[0368] Ar H3 and Ar H4 Each independently represents a monovalent heterocyclic group containing a group represented by =N- in the ring, a hydrogen atom, a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryloxy group or an aryl group, and these groups may have a substituent.

[0369] L H2 represents a divalent heterocyclic group, an alkylene group, a cycloalkylene group or an arylene group containing a group represented by =N- in the ring, and these groups may have a substituent. H2 In the case of, they are optionally the same or different. H2 At least one of them is a divalent heterocyclic group containing a group represented by =N- in the ring.]

[0370] Ar H3 and Ar H4 It is preferably a monovalent heterocyclic group, a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or an aryl group containing a group represented by =N- in the ring, more preferably a monovalent heterocyclic group, an alkyl group, a cycloalkyl group or an aryl group containing a group represented by =N- in the ring, further preferably a monovalent heterocyclic group or an aryl group containing a group represented by =N- in the ring, and particularly preferably an aryl group, and these groups may have a substituent.

[0371] Ar H3 and Ar H4 The examples and preferred ranges of the aryl groups shown are similar to those of Ar T1 The examples and preferred ranges of the aryl group are the same as those shown above.

[0372] The monovalent heterocyclic group containing a group represented by =N- in the ring is a group obtained by removing one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring from the heterocyclic group containing a group represented by =N- in the ring.

[0373] n H2 It is preferably an integer of 1 to 5, more preferably an integer of 1 to 3, further preferably 1 or 2, and particularly preferably 1.

[0374] L H2 It is preferably a divalent heterocyclic group or an arylene group containing a group represented by =N- in the ring, and more preferably a divalent heterocyclic group containing a group represented by =N- in the ring, and these groups may have a substituent.

[0375] L H2 The examples and preferred ranges of the arylene group shown are similar to those of L T1 The examples and preferred ranges of the arylene group are the same as those shown above.

[0376] The divalent heterocyclic group containing a group represented by =N- in the ring is a group obtained by removing two hydrogen atoms directly bonded to a carbon atom or a heteroatom constituting the ring from the heterocyclic group containing a group represented by =N- in the ring.

[0377] As L H2 ,Ar H3 and Ar H4 The substituents which may be present are monovalent heterocyclic groups, alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkyloxy groups or aryl groups containing a group represented by =N-, more preferably monovalent heterocyclic groups, alkyl groups, cycloalkyl groups or aryl groups containing a group represented by =N-, and further preferably alkyl groups, cycloalkyl groups or aryl groups, and these groups may further have substituents.

[0378] L H2 ,Ar H3 and Ar H4 Examples and preferred ranges of the aryl group in the optional substituent are similar to those of Ar T1 The examples and preferred ranges of the aryl group are the same as those shown above.

[0379] As L H2 ,Ar H3 and Ar H4 The substituent that may be further possessed on the substituent that may be possessed is preferably an alkyl group, a cycloalkyl group, an alkoxy group or a cycloalkoxy group, and more preferably an alkyl group or a cycloalkyl group.

[0380] Examples of the compound represented by formula (H-1) include compounds represented by formula (H-101) to (H-106) and (H-113) to (H-118). Examples of the compound represented by formula (H-2) include compounds represented by formula (H-107) to (H-112).

[0381] [Chemistry 57]

[0382]

[0383] [Chemistry 58]

[0384]

[0385] [Chemistry 59]

[0386]

[0387] [Chemistry 60]

[0388]

[0389] Examples of the polymer compound used for the host material include a polymer compound as a hole transport material described later and a polymer compound as an electron transport material described later.

[0390] [Polymer host]

[0391] A polymer compound preferred as the host compound (hereinafter referred to as a "polymer host") is preferably a polymer compound containing a structural unit represented by formula (Y).

[0392] Ar Y1 The arylene group represented is more preferably a group represented by formula (A-1) to (1-10), formula (A-19) or formula (A-20), further preferably a group represented by formula (A-1) to (A-3), formula (A-6) to (A-10), formula (A-19) or formula (A-20), particularly preferably a group represented by formula (A-1) to (A-3), formula (A-7) to (A-9), formula (A-19) or formula (A-20), and particularly preferably a group represented by formula (A-1), formula (A-2), formula (A-7), formula (A-9) or formula (A-19), and these groups optionally have substituents.

[0393] Ar Y1 The divalent heterocyclic group shown is more preferably a group shown by formula (AA-1) to formula (AA-4), formula (AA-10) to formula (AA-15), formula (AA-18) to formula (AA-21), formula (AA-33) or formula (AA-34), and is further preferably a group shown by formula (AA-4), formula (AA-10), formula (AA-12), formula (AA-14) or formula (AA-33), and these groups optionally have substituents.

[0394] Ar Y1 The more preferred range and further preferred range of the arylene group and the divalent heterocyclic group in the divalent group formed by directly bonding at least one arylene group and at least one divalent heterocyclic group are the same as those of Ar Y1 The more preferred range and further preferred range of the arylene group and the divalent heterocyclic group are the same as those described above.

[0395] 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 formulae, which may have a substituent.

[0396] [Chemistry 61]

[0397]

[0398] [Where R XX represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.]

[0399] R XX Preferred is an alkyl group, a cycloalkyl group or an aryl group, and these groups may have a substituent.

[0400] Ar Y1 The substituent optionally possessed by the group shown is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkyloxy group, an aryl group, a monovalent heterocyclic group, a substituted amino group, a fluorine atom or a cyano group, more preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkyloxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group, further preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, particularly preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups optionally have substituents.

[0401] As Ar Y1 The substituent optionally possessed by the group shown in the figure is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkyloxy group, an aryl group, a monovalent heterocyclic group, a substituted amino group, a fluorine atom or a cyano group, more preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, further preferably an alkyl group or a cycloalkyl group, and these groups optionally have a substituent.

[0402] As the structural unit represented by formula (Y), for example, the structural units represented by formula (Y-1) to formula (Y-10) can be listed. From the viewpoint of the external quantum efficiency of the light-emitting element of the present invention, the structural units represented by formula (Y-1) to formula (Y-3) are preferred. From the viewpoint of the electron transport property of the light-emitting element of the present invention, the structural units represented by formula (Y-4) to formula (Y-7) are preferred. From the viewpoint of the hole transport property of the light-emitting element of the present invention, the structural units represented by formula (Y-8) to formula (Y-10) are preferred.

[0403] [Chemistry 62]

[0404]

[0405] [Wherein,

[0406] R Y1 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 may have a substituent.Y1 In the case of Y1 They are optionally bonded to each other and together with the carbon atoms to which they are bonded form a ring.

[0407] n Y1 Indicates 4. ]

[0408] R Y1 It 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, further preferably a hydrogen atom, an alkyl group or a cycloalkyl group, and particularly preferably a hydrogen atom or an alkyl group, and these groups may have a substituent.

[0409] R Y1 Examples and preferred ranges of the optional substituents are similar to those of Ar Y1 Examples and preferred ranges of substituents that may be further possessed by the substituents that the groups shown above may have are the same as those of the substituents that may be further possessed by the groups shown above.

[0410] The structural unit represented by formula (Y-1) is preferably a structural unit represented by formula (Y-1-1) or formula (Y-1-2), and more preferably a structural unit represented by formula (Y-1-1).

[0411] [Chemistry 63]

[0412]

[0413] [Where R Y1 Means the same as above.]

[0414] The structural unit represented by formula (Y-1-1) is preferably a structural unit represented by formula (Y-1-1′) or formula (Y-1-1″), and more preferably a structural unit represented by formula (Y-1-1′).

[0415] The structural unit represented by formula (Y-1-2) is preferably a structural unit represented by formula (Y-1-2′) or formula (Y-1-2″), and more preferably a structural unit represented by formula (Y-1-2′).

[0416] [Chemistry 64]

[0417]

[0418] [Wherein,

[0419] R Y1 Means the same as above.

[0420] R Y11 represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. Y11Optional: same or different.]

[0421] R Y11 An alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group is preferred, an alkyl group, a cycloalkyl group or an aryl group is more preferred, an alkyl group or a cycloalkyl group is further preferred, and an alkyl group is particularly preferred. These groups may have a substituent.

[0422] R Y11 Examples and preferred ranges of the optional substituents are similar to those of Ar Y1 Examples and preferred ranges of substituents that may be further possessed by the substituents that the groups shown above may have are the same as those of the substituents that may be further possessed by the groups shown above.

[0423] [Chemistry 65]

[0424]

[0425] [Wherein,

[0426] R Y1 Means the same as above.

[0427] X Y1 Indicates -C(R Y2 )2-、-C(R Y2 )=C(R Y2 )-or-C(R Y2 )2-C(R Y2 )2-. Y2 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 may have a substituent. Y2 Optional same or different, R Y2 They are optionally bonded to each other and together with the carbon atoms to which they are bonded form a ring.

[0428] n Y2 Indicates 6. ]

[0429] R Y2 It 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 may have a substituent.

[0430] R Y2 Examples and preferred ranges of the optional substituents are similar to those of Ar Y1 Examples and preferred ranges of substituents that may be further possessed by the substituents that the groups shown above may have are the same as those of the substituents that may be further possessed by the groups shown above.

[0431] In X Y1 In, -C(R Y2 )2- in the group represented by two R Y2The combination of is preferably: both are alkyl or cycloalkyl, both are aryl, both are monovalent heterocyclic groups, or one is alkyl or cycloalkyl and the other is aryl or monovalent heterocyclic group, more preferably one is alkyl or cycloalkyl and the other is aryl, and these groups may have substituents. Y2 are optionally bonded to each other and together with the atoms to which they are bonded form a ring, in R Y2 When a ring is formed, as -C(R Y2 )2-, preferably a group represented by formula (Y-A1) to formula (Y-A5), more preferably a group represented by formula (Y-A4), and these groups optionally have substituents.

[0432] [Chemistry 66]

[0433]

[0434] In X Y1 In, -C(R Y2 )=C(R Y2 )-2 R in the group shown Y2 The combination of is preferably: both are alkyl groups or cycloalkyl groups, or one is an alkyl group or cycloalkyl group and the other is an aryl group, and these groups may have a substituent.

[0435] In X Y1 In, -C(R Y2 )2-C(R Y2 ) 2- The four R Y2 Preferably, it is an alkyl group or a cycloalkyl group which may have a substituent. Y2 are optionally bonded to each other and together with the atoms to which they are bonded form a ring, in R Y2 When a ring is formed, -C(R Y2 )2-C(R Y2 The group represented by )2- is preferably a group represented by the formula (Y-B1) to (Y-B5), and more preferably a group represented by the formula (Y-B3), and these groups optionally have substituents.

[0436] [Chemistry 67]

[0437]

[0438] [Where R Y2 Means the same as above.]

[0439] The structural unit represented by formula (Y-2) is preferably a structural unit represented by formula (Y-2-1) to (Y-2-4), and more preferably a structural unit represented by formula (Y-2-1) to (Y-2-3).

[0440] [Chemistry 68]

[0441]

[0442] [Where R Y1 , R Y11 and X Y1 Means the same as above.]

[0443] [Chemistry 69]

[0444]

[0445] [Where n Y1 、n Y2 , R Y1 and X Y1 Means the same as above.]

[0446] The structural unit represented by formula (Y-3) is preferably a structural unit represented by formula (Y-3-1) to formula (Y-3-4), and more preferably a structural unit represented by formula (Y-3-1) to formula (Y-3-3).

[0447] [Chemistry 70]

[0448]

[0449] [Chemistry 71]

[0450]

[0451] [Where n Y2 、n Y2 , R Y1 , R Y11 and X Y1 Means the same as above.]

[0452] [Chemistry 72]

[0453]

[0454] [Chemistry 73]

[0455]

[0456] [Wherein,

[0457] R Y1 Means the same as above.

[0458] R Y3 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 may have a substituent.]

[0459] R Y3An alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group is preferred, an aryl group or a monovalent heterocyclic group is more preferred, and an aryl group is further preferred. These groups may have a substituent.

[0460] R Y3 Examples and preferred ranges of the optional substituents are similar to those of Ar Y1 Examples and preferred ranges of substituents that may be further possessed by the substituents that the groups shown above may have are the same as those of the substituents that may be further possessed by the groups shown above.

[0461] The structural unit represented by formula (Y-4) is preferably a structural unit represented by formula (Y-4').

[0462] The structural unit represented by the formula (Y-6) is preferably a structural unit represented by the formula (Y-6').

[0463] [Chemistry 74]

[0464]

[0465] [Where R Y1 and R Y3 Means the same as above.]

[0466] [Chemistry 75]

[0467]

[0468] [Where R Y1 Means the same as above. Y4 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 may have a substituent.]

[0469] R Y4 An alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group is preferred, an aryl group or a monovalent heterocyclic group is more preferred, and an aryl group is further preferred. These groups may have a substituent.

[0470] R Y4 Examples and preferred ranges of the optional substituents are similar to those of Ar Y1 Examples and preferred ranges of substituents that may be further possessed by the substituents that the groups shown above may have are the same as those of the substituents that may be further possessed by the groups shown above.

[0471] As the structural unit represented by formula (Y), for example, the structural unit containing an arylene group represented by formula (Y-101) to formula (Y-121), the structural unit containing a divalent heterocyclic group represented by formula (Y-201) to formula (Y-206), and the structural unit containing a divalent group directly bonded to at least one arylene group and at least one divalent heterocyclic group represented by formula (Y-300) to formula (Y-304).

[0472] [Chemistry 76]

[0473]

[0474] [Chemistry 77]

[0475]

[0476] [Chemistry 78]

[0477]

[0478] [Chemistry 79]

[0479]

[0480] [Chemistry 80]

[0481]

[0482] [Chemistry 81]

[0483]

[0484] [Chemistry 82]

[0485]

[0486] [Chemistry 83]

[0487]

[0488] [Chemistry 84]

[0489]

[0490] From the viewpoint that the light-emitting element of the present invention has excellent external quantum efficiency, Ar Y1 The amount of the structural unit represented by the formula (Y) which is an arylene group is preferably 0.5 to 99 mol %, more preferably 30 to 95 mol %, and further preferably 50 to 95 mol % based on the total amount of the structural units contained in the polymer main body.

[0491] From the viewpoint of excellent charge transport properties of the light-emitting element of the present invention, Ar Y1 The amount of the structural unit represented by formula (Y) which is a divalent heterocyclic group or a divalent group formed by direct bonding of at least one arylene group and at least one divalent heterocyclic group is preferably 0.5 to 50 mol %, more preferably 1 to 40 mol %, and even more preferably 5 to 30 mol % based on the total amount of the structural units contained in the polymer main body.

[0492] The polymer host may contain only one type of the structural unit represented by the formula (Y), or may contain two or more types of the structural unit represented by the formula (Y).

[0493] From the viewpoint of excellent hole transporting properties, the polymer host preferably further includes a structural unit represented by the following formula (X).

[0494] [Chemistry 85]

[0495]

[0496] [Wherein,

[0497] a Z1 and a X2 Each independently represents an integer greater than 0.

[0498] Ar X1 and Ar X3 Each independently represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent.

[0499] Ar X2 and Ar X4 Each independently 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, and these groups may have a substituent. X2 and Ar X4 In the case of , they are optionally the same or different.

[0500] R X1 , R X2 and R X3 Each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. X2 and R X3 In the case of , they are optionally the same or different.]

[0501] From the viewpoint that the external quantum efficiency of the light-emitting element of the present invention is more excellent, a X1 It is preferably 2 or less, more preferably 1 or 0, and further preferably 0.

[0502] From the viewpoint that the external quantum efficiency of the light-emitting element of the present invention is more excellent, a X2 It is preferably 2 or less, and more preferably 0.

[0503] R X1 , R X2 and R X3 An alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group is preferred, an aryl group or a monovalent heterocyclic group is more preferred, and an aryl group is further preferred. These groups may have a substituent.

[0504] Ar X1 and Ar X3The arylene group represented by formula (A-1) or formula (A-9) is more preferably a group represented by formula (A-1), and further preferably a group represented by formula (A-1), and these groups may have a substituent.

[0505] Ar X1 and Ar X3 The divalent heterocyclic group is more preferably a group represented by formula (AA-1), formula (AA-2) or formula (AA-7) to formula (AA-26), and these groups may have a substituent.

[0506] Ar X1 and Ar X3 An arylene group which may have a substituent is preferred.

[0507] As Ar X2 and Ar X4 The arylene group shown is more preferably a group shown by formula (A-1), formula (A-6), formula (A-7), formula (A-9) to formula (A-11) or formula (A-19), and these groups optionally have a substituent.

[0508] Ae X2 and Ar X4 The more preferred range of the divalent heterocyclic group is X1 and Ar X3 The more preferred range of the divalent heterocyclic group is the same as that shown.

[0509] Ar X2 and Ar X4 The more preferred ranges and further preferred ranges of the arylene group and the divalent heterocyclic group in the divalent group formed by directly bonding at least one arylene group and at least one divalent heterocyclic group are the same as Ar X1 and Ar X3 The more preferred range and further preferred range of the arylene group and the divalent heterocyclic group are the same as those shown above.

[0510] As Ar X2 and Ar X4 The divalent group formed by directly bonding at least one arylene group and at least one divalent heterocyclic group is exemplified by Ar of formula (Y): Y1 The divalent group is the same as the divalent group formed by directly bonding at least one kind of arylene group and at least one kind of divalent heterocyclic group shown in the foregoing.

[0511] Ar X2 and Ar X4 An arylene group which may have a substituent is preferred.

[0512] Ar X1 ~Ar X4 and R X1 ~R X3Examples and preferred ranges of substituents that the groups shown in the table may optionally have are similar to those of Ar Y1 Examples and preferred ranges of substituents that the groups shown may have are the same.

[0513] Ar X1 ~Ar X4 and R X1 ~R X3 Examples and preferred ranges of substituents that may be further possessed by the substituents that the groups represented by Y1 Examples and preferred ranges of substituents that may be further possessed by the substituents that the groups shown above may have are the same as those of the substituents that may be further possessed by the groups shown above.

[0514] The structural unit represented by formula (X) is preferably a structural unit represented by formula (X-1) to formula (X-7), more preferably a structural unit represented by formula (X-1) to formula (X-6), and further preferably a structural unit represented by formula (X-3) to (X-6).

[0515] [Chemistry 86]

[0516]

[0517] [Chemistry 87]

[0518]

[0519] [Chemistry 88]

[0520]

[0521] [Chemistry 89]

[0522]

[0523] [Where R X4 and R X5 Each independently represents 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 may have a substituent. X4 Optional same or different. X5 Optional, same or different, adjacent R X5 They are optionally bonded to each other and together with the carbon atoms to which they are bonded form a ring.]

[0524] R X4 It is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkyloxy group, an aryl group or a monovalent heterocyclic group, more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, further preferably a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, particularly preferably a hydrogen atom or an alkyl group, and these groups may further have a substituent.

[0525] R X5 It is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkyloxy group, an aryl group or a monovalent heterocyclic group, more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, further preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, particularly preferably an alkyl group or an aryl group, and these groups may further have a substituent.

[0526] R X4 and R X5 Examples and preferred ranges of substituents that the groups shown in the table may optionally have are similar to those of Ar Y1 Examples and preferred ranges of substituents that may be further possessed by the substituents that the groups shown above may have are the same as those of the substituents that may be further possessed by the groups shown above.

[0527] From the viewpoint of excellent hole transport properties, the amount of the structural unit represented by formula (X) is preferably 0.1 to 50 mol %, more preferably 1 to 40 mol %, and even more preferably 5 to 30 mol % based on the total amount of the structural units contained in the polymer host.

[0528] Examples of the structural unit represented by formula (X) include structural units represented by formula (X1-1) to formula (X1-11), and preferably structural units represented by formula (X1-3) to formula (X1-10).

[0529] [Chemistry 90]

[0530]

[0531] [Chemistry 91]

[0532]

[0533] [Chemistry 92]

[0534]

[0535] [Chemistry 93]

[0536]

[0537] [Chemistry 94]

[0538]

[0539] [Chemistry 95]

[0540]

[0541] The polymer host may contain only one type of the structural unit represented by the formula (X), or may contain two or more types of the structural unit represented by the formula (X).

[0542] Examples of the polymer host include polymer compounds P-51 to P-6.

[0543] [Table 1]

[0544]

[0545] [In the table, p, q, r, s and t represent the molar ratio of each structural unit. p+q+r+s+t=100, and 100≥p+q+r+s≥70. Other structural units refer to structural units other than the structural units represented by formula (Y) and the structural units represented by formula (X).]

[0546] The main polymer may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, and may be in other forms, but is preferably a copolymer obtained by copolymerizing a plurality of raw material monomers.

[0547] The polystyrene-equivalent number average molecular weight of the main polymer is preferably 5×10 3 ~1×10 6 , more preferably 1×10 4 ~5×10 5 , and more preferably 1.5×10 4 ~1.5×10 5 .

[0548] [Method for producing polymer host]

[0549] The polymer main body can be produced using a known polymerization method described in Chemical Review (Chem. Rev.), Vol. 109, pp. 897-1091 (2009), etc., and examples thereof include polymerization methods using coupling reactions using transition metal catalysts such as Suzuki reaction, Yamamoto reaction, Buchwald reaction, Stille reaction, Negishi reaction and Kumada reaction.

[0550] In the above polymerization method, examples of methods for adding monomers include: a method of adding all the monomers at once to the reaction system; a method of adding a portion of the monomers to react and then adding the remaining monomers at once, continuously or in batches; a method of adding the monomers continuously or in batches, etc.

[0551] Examples of the transition metal catalyst include a palladium catalyst and a nickel catalyst.

[0552] The post-treatment of the polymerization reaction is carried out by a single or combined known method, for example, a method of removing water-soluble impurities by liquid separation; a method of adding the reaction solution after the polymerization reaction to a lower alcohol such as methanol, filtering the precipitated precipitate, and drying it, etc. In the case where the purity of the polymer main body is low, it can be purified by common methods such as recrystallization, reprecipitation, continuous extraction using a Soxhlet extractor, column chromatography, etc.

[0553] [First composition]

[0554] The first organic layer may be a layer containing a composition (hereinafter also referred to as "first composition") comprising a compound (T) and at least one material selected from the above-mentioned host material, hole transport material, hole injection material, electron transport material, electron injection material, fluorescent material and antioxidant. However, the hole transport material, hole injection material, electron transport material, electron injection material and fluorescent material are different from the compound (T).

[0555] [Hole transport material]

[0556] The hole transport material is classified into a low molecular weight compound and a high molecular weight compound, and the high molecular weight compound is preferred. The hole transport material may have a crosslinking group.

[0557] Examples of the polymer compound include polyvinyl carbazole and its derivatives; polyarylene and its derivatives having an aromatic amine structure on the side chain or the main chain. The polymer compound may be a compound having an electron accepting site. Examples of the electron accepting site include fullerene, tetrafluorotetracyanoquinodimethane, tetracyanoethylene, trinitrofluorenone, etc., preferably fullerene.

[0558] In the first composition, the amount of the hole transport material is usually 0.1 to 1000 parts by mass, preferably 1 to 400 parts by mass, and more preferably 5 to 150 parts by mass, based on 100 parts by mass of the compound (T).

[0559] The hole transport material may be used alone or in combination of two or more.

[0560] [Electron transport materials]

[0561] The electron transport material is classified into a low molecular weight compound and a high molecular weight compound. The electron transport material may have a crosslinking group.

[0562] Examples of the low molecular weight compound include metal complexes having 8-hydroxyquinoline as a ligand, oxadiazole, anthraquinone dimethane, benzoquinone, naphthoquinone, anthraquinone, tetracyanoanthraquinone dimethane, fluorenone, diphenyl dicyanoethylene, diphenoquinone, and derivatives thereof.

[0563] Examples of the polymer compound include polyphenylene, polyfluorene, and derivatives thereof. The polymer compound may be doped with a metal.

[0564] In the first composition, the amount of the electron transport material added is usually 0.1 to 1000 parts by mass, preferably 1 to 400 parts by mass, and more preferably 5 to 150 parts by mass, based on 100 parts by mass of the compound (T).

[0565] The electron transport material may be used alone or in combination of two or more.

[0566] [Hole injection materials and electron injection materials]

[0567] The hole injection material and the electron injection material are each classified into a low molecular weight compound and a high molecular weight compound. The hole injection material and the electron injection material may have a crosslinking group.

[0568] Examples of the low molecular weight compound include metal phthalocyanine such as copper phthalocyanine; carbon; metal oxides such as molybdenum and tungsten; and metal fluorides such as lithium fluoride, sodium fluoride, cesium fluoride, and potassium fluoride.

[0569] Examples of the polymer compound include conductive polymers such as polyaniline, polythiophene, polypyrrole, polyphenylenevinylene, polythienylenevinylene, polyquinoline, polyquinoxaline, and derivatives thereof; and polymers containing an aromatic amine structure in the main chain or a side chain.

[0570] In the first composition, the amount of the hole injection material and the electron injection material is usually 0.1 to 1000 parts by mass, preferably 1 to 400 parts by mass, and more preferably 5 to 150 parts by mass, per 100 parts by mass of the compound (T).

[0571] The electron injection material and the hole injection material may be used alone or in combination of two or more.

[0572] [Ion doping]

[0573] When the hole injection material or the electron injection material includes a conductive polymer, the conductivity of the conductive polymer is preferably 1×10 -5 S / cm~1×10 3 In order to make the conductivity of the conductive polymer fall within this range, the conductive polymer may be doped with an appropriate amount of ions.

[0574] Regarding the type of ions to be doped, if it is a hole injection material, it is an anion, and if it is an electron injection material, it is a cation. Examples of anions include polystyrene sulfonate ions, alkylbenzene sulfonate ions, and camphor sulfonate ions. Examples of cations include lithium ions, sodium ions, potassium ions, and tetrabutylammonium ions.

[0575] The ions to be doped may be used alone or in combination of two or more.

[0576] [Fluorescent materials]

[0577] Fluorescent materials are classified into low molecular weight compounds and high molecular weight compounds. Fluorescent materials may have a cross-linking group.

[0578] Examples of the low molecular weight compound include naphthalene and its derivatives, anthracene and its derivatives, and perylene and its derivatives.

[0579] Examples of the polymer compound include polymer compounds containing phenylene, naphthalene diyl, anthracene diyl, fluorene diyl, phenanthrene diyl, dihydrophenanthrene diyl, a group represented by formula (X), carbazole diyl, phenoxazine diyl, phenothiazine diyl, pyrene diyl, and the like.

[0580] In the first composition, the amount of the fluorescent material added is usually 0.1 to 1000 parts by mass, preferably 0.1 to 400 parts by mass, and more preferably 5 to 150 parts by mass, based on 100 parts by mass of the compound (T).

[0581] When the first composition is a composition comprising a compound (T) and a fluorescent light-emitting material, the compound (T) is preferably a host material.

[0582] When the first composition is a composition comprising a compound (T) and a fluorescent material, and the compound (T) is a main material, the content of the fluorescent material is generally 0.1 to 50 parts by mass, preferably 1 to 45 parts by mass, more preferably 5 to 40 parts by mass, and further preferably 10 to 30 parts by mass, when the total of the compound (T) and the fluorescent material is set to 100 parts by mass.

[0583] When the first composition is a composition comprising a compound (T) and a fluorescent material, and the compound (T) is a main material, from the perspective of better external quantum efficiency of the light-emitting element of the present invention, when the total of the compound (T) and the fluorescent material is set to 100 parts by mass, the content of the fluorescent material is preferably 0.01 to 50 parts by mass, more preferably 0.1 to 20 parts by mass, and more preferably 0.5 to 5 parts by mass.

[0584] The fluorescent light-emitting materials may be used alone or in combination of two or more.

[0585] [Antioxidant]

[0586] The antioxidant may be any compound that is soluble in the same solvent as the compound (T) and does not inhibit light emission and charge transport, and examples thereof include phenolic antioxidants and phosphorus antioxidants.

[0587] In the first composition, the amount of the antioxidant added is usually 0.001 to 10 parts by mass based on 100 parts by mass of the compound (T).

[0588] The antioxidants may be used alone or in combination of two or more.

[0589] [First Ink]

[0590] The composition containing compound (T) and a solvent (hereinafter also referred to as "first ink") can be suitably used for coating methods such as spin coating, casting, micro-gravure coating, gravure coating, rod coating, roller coating, wire bar coating, dip coating, spray coating, screen printing, flexographic printing, offset printing, inkjet printing, capillary coating, and nozzle coating.

[0591] The viscosity of the first ink can be adjusted according to the type of coating method. When applied to a printing method such as inkjet printing in which a solution is ejected through a discharge device, the viscosity of the first ink is preferably 1 to 20 mPa·s at 25° C. from the perspective of preventing clogging and flight deflection during ejection.

[0592] The solvent contained in the first ink is preferably a solvent that can dissolve or evenly disperse the solid components in the ink. Examples of the solvent include: chlorine-based solvents such as 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, and o-dichlorobenzene; ether-based solvents such as tetrahydrofuran, dioxane, anisole, and 4-methylanisole; aromatic hydrocarbon-based solvents such as toluene, xylene, trimethylbenzene, ethylbenzene, n-hexylbenzene, and cyclohexylbenzene; cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane, n-dodecane, and dimethylbenzene. Aliphatic hydrocarbon solvents such as cyclohexane; ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone, acetophenone, etc.; ester solvents such as ethyl acetate, butyl acetate, ethyl cellosolve acetate, methyl benzoate, phenyl acetate, etc.; polyol solvents such as ethylene glycol, glycerol, 1,2-hexanediol, etc.; alcohol solvents such as isopropyl alcohol, cyclohexanol, etc.; sulfoxide solvents such as dimethyl sulfoxide, etc.; amide solvents such as N-methyl-2-pyrrolidone, N,N-dimethylformamide, etc. The solvents may be used alone or in combination of two or more.

[0593] In the first ink, the amount of the solvent blended is generally 1,000 to 100,000 parts by mass, preferably 2,000 to 20,000 parts by mass, based on 100 parts by mass of the compound (T).

[0594] <Second organic layer>

[0595] The second organic layer is a layer containing a crosslinked body of a polymer compound including a crosslinked structural unit (hereinafter also referred to as “polymer compound of the second organic layer”).

[0596] The crosslinked product of the polymer compound of the second organic layer is obtained by making the polymer compound of the second organic layer into a crosslinked state by the above-mentioned method.

[0597] [Polymer compound of the second organic layer]

[0598] From the perspective of achieving better external quantum efficiency of the light-emitting element of the present invention, the energy level of the lowest triplet excited state of the polymer compound in the second organic layer is preferably 2.30 eV or more, more preferably 2.33 eV or more, further preferably 2.40 eV or more, and particularly preferably 2.46 eV or more.

[0599] From the perspective of excellent stability of the polymer compound of the second organic layer, the energy level of the lowest triplet excited state of the polymer compound of the second organic layer is preferably 4.00 eV or less, more preferably 3.50 eV or less, further preferably 3.00 eV or less, particularly preferably 2.70 eV or less, and particularly preferably 2.60 eV or less.

[0600] From the perspective of better external quantum efficiency of the light-emitting element of the present invention and excellent stability of the polymer compound of the second organic layer, the energy level of the lowest triplet excited state of the polymer compound of the second organic layer is preferably greater than 2.30 eV and less than 4.50 eV, more preferably greater than 2.33 eV and less than 4.00 eV, further preferably greater than 2.40 eV and less than 3.50 eV, and particularly preferably greater than 2.46 eV and less than 3.00 eV.

[0601] The energy level of the lowest triplet excited state of the polymer compound can be obtained by preparing a film containing the polymer compound, measuring the phosphorescence spectrum of the film at 77K, and converting the shortest wavelength maximum peak wavelength in the obtained phosphorescence spectrum into energy. The thickness of the film is usually 10nm to 1μm. The film formation method includes coating methods such as spin coating and drop casting, preferably drop casting.

[0602] The magnitude relationship of the energy levels of the lowest triplet excited states of polymer compounds can be compared using computational science methods. Specifically, the energy levels of the lowest triplet excited states of each polymer compound can be calculated using computational science methods, and the magnitude relationship can be compared using the calculated results.

[0603] In the computational science method, Gaussian09 was used as a quantum chemical calculation program, and the ground state of the dimer of the monomer unit was structurally optimized using the density functional method at the B3LYP level, and 6-31G* was used as the basis function. In addition, the energy level of the lowest triplet excited state of the polymer compound was calculated using the time-dependent density functional method at the B3LYP level. In the case where an atom for which 6-31G* cannot be used is included, LANL2DZ is used for the atom. In the case where the polymer compound contains only one monomer unit, the lowest excited triplet energy is calculated for the dimer of the monomer unit as the lowest excited triplet energy of the polymer compound. In the case where the polymer compound contains two or more monomer units, the lowest excited triplet energy is calculated for all dimers that may be generated in the polymerization of monomer units containing a molar ratio of 1% or more, and the smallest value among them is taken as the lowest excited triplet energy of the polymer compound.

[0604] From the viewpoint of excellent external quantum efficiency of the light-emitting element of the present invention, the polymer compound of the second organic layer is preferably a polymer compound containing a crosslinking structural unit having at least one crosslinking group selected from the crosslinking group A group.

[0605] As a cross-linking group selected from the cross-linking group A group, from the perspective of better external quantum efficiency of the light-emitting element of the present invention, preferably it is a cross-linking group represented by formula (XL-1) to formula (XL-4), formula (XL-7) to formula (XL-10) or formula (XL-14) to formula (XL-17), more preferably a cross-linking group represented by formula (XL-1), formula (XL-3), formula (XL-9), formula (XL-10), formula (XL-16) or formula (XL-17), further preferably a cross-linking group represented by formula (XL-1), formula (XL-16) or formula (XL-17), particularly preferably a cross-linking group represented by formula (XL-1) or formula (XL-17), and particularly preferably a cross-linking group represented by formula (XL-17).

[0606] As a cross-linking group selected from the cross-linking group A group, from the perspective of better external quantum efficiency of the light-emitting element of the present invention and more preferred cross-linking properties of the polymer compound of the second organic layer, preferably a cross-linking group represented by formula (XL-2) to (XL-4), formula (XL-7) to (XL-10), formula (XL-14), formula (XL-15) or formula (XL-17), more preferably a cross-linking group represented by formula (XL-9), formula (XL-10) or formula (XL-17), and particularly preferably a cross-linking group represented by formula (XL-17).

[0607] The structural unit having at least one crosslinking group selected from the crosslinking group A contained in the polymer compound of the second organic layer is preferably a structural unit represented by formula (2) or a structural unit represented by formula (2'), and may be a structural unit shown below.

[0608] [Chemistry 96]

[0609]

[0610] When the polymer compound of the second organic layer contains two or more structural units having at least one crosslinking group selected from the crosslinking group group A, it is preferred that the crosslinking groups of at least two structural units of the structural unit having at least one crosslinking group selected from the crosslinking group group A are different from each other. As a combination of different crosslinking groups, a combination of a crosslinking group represented by formula (XL-1), formula (XL-2), formula (XL-5) to formula (XL-8) or formula (XL-14) to formula (XL-16) and a crosslinking group represented by formula (XL-3), formula (XL-4), formula (XL-13) or formula (XL-17) is preferred, a combination of a crosslinking group represented by formula (XL-1) or formula (XL-16) and a crosslinking group represented by formula (XL-17) is more preferred, and a combination of a crosslinking group represented by formula (XL-1) and a crosslinking group represented by formula (XL-17) is further preferred.

[0611] The structural unit represented by formula (2)

[0612] From the viewpoint of further improving the external quantum efficiency of the light-emitting element of the present invention, nA is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, and even more preferably 1.

[0613] From the viewpoint of further improving the external quantum efficiency of the light-emitting element of the present invention, n is preferably 2.

[0614] From the viewpoint that the external quantum efficiency of the light-emitting element of the present invention is more excellent, Ar 3 An aromatic hydrocarbon group which may have a substituent is preferred.

[0615] Ar 3 The aromatic hydrocarbon group shown has usually 6 to 60 carbon atoms, not including the carbon atoms of the substituent, preferably 6 to 30, more preferably 6 to 18 carbon atoms.

[0616] Ar 3 Examples and preferred ranges of the arylene moiety after removing n substituents from the aromatic hydrocarbon group shown are similar to those of Ar Y1 The examples and preferred ranges of the arylene group are the same as those shown above.

[0617] Ar 3The heterocyclic group shown has usually 2 to 60 carbon atoms, not including the carbon atoms of the substituent, preferably 3 to 30, more preferably 4 to 18 carbon atoms.

[0618] Ar 3 Examples and preferred ranges of the divalent heterocyclic moiety after removing n substituents from the heterocyclic group shown in Y1 The examples and preferred ranges of the divalent heterocyclic group are the same as those shown above.

[0619] Ar 3 Examples and preferred ranges of substituents that the groups shown in the table may optionally have are similar to those of Ar Y1 Examples and preferred ranges of substituents that the groups shown may have are the same.

[0620] Ar 3 Examples and preferred ranges of substituents that may be further possessed by the substituents that the groups represented by Y1 Examples and preferred ranges of substituents that may be further possessed by the substituents that the groups shown above may have are the same as those of the substituents that may be further possessed by the groups shown above.

[0621] L A The number of carbon atoms of the alkylene group represented by L excluding the number of carbon atoms of the substituent is usually 1 to 20, preferably 1 to 15, and more preferably 1 to 10. A The cycloalkylene group shown generally has 3 to 20 carbon atoms, not including the carbon atoms of the substituent.

[0622] L A The alkylene and cycloalkylene groups shown may have a substituent, and examples thereof include methylene, ethylene, propylene, butylene, hexylene, cyclohexylene, octylene, and groups in which hydrogen atoms in these groups are substituted with alkyl, cycloalkyl, alkoxy, cycloalkoxy, aryl, monovalent heterocyclic group, fluorine atom, etc.

[0623] L A The examples and preferred ranges of the arylene group shown are similar to those of Ar Y1 The examples and preferred ranges of the arylene group shown in the figure are the same. From the perspective of the better external quantum efficiency of the light-emitting device of the present invention, L A The arylene group shown is preferably a phenylene group or a fluorenediyl group, more preferably a m-phenylene group, a p-phenylene group, a fluorene-2,7-diyl group, or a fluorene-9,9-diyl group, and these groups may further have a substituent.

[0624] L A Examples and preferred ranges of the divalent heterocyclic group shown are similar to those of Ar Y1 The examples and preferred ranges of the divalent heterocyclic group are the same as those shown above.

[0625] From the perspective of facilitating the production of the polymer compound of the second organic layer, L A It is preferably an arylene group or an alkylene group, more preferably a phenylene group, a fluorenediyl group or an alkylene group, and further preferably an alkylene group, and these groups may have a substituent.

[0626] L A The substituent optionally possessed by the group shown is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkyloxy group, an aryl group, a monovalent heterocyclic group, a substituted amino group, a fluorine atom, a cyano group or a cross-linking group selected from the cross-linking group A group, more preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkyloxy group, an aryl group, a monovalent heterocyclic group or a cross-linking group selected from the cross-linking group A group, further preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, particularly preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups optionally have substituents.

[0627] L A Examples and preferred ranges of substituents that may be further possessed by the substituents that the groups represented by Y1 Examples and preferred ranges of substituents that may be further possessed by the substituents that the groups shown above may have are the same as those of the substituents that may be further possessed by the groups shown above.

[0628] As the cross-linking group represented by X, from the perspective of better external quantum efficiency of the light-emitting element of the present invention, preferably it is a cross-linking group represented by formula (XL-1) to formula (XL-4), formula (XL-7) to formula (XL-10) or formula (XL-14) to formula (XL-17), more preferably a cross-linking group represented by formula (XL-1), formula (XL-3), formula (XL-9), formula (XL-10), formula (XL-16) or formula (XL-17), further preferably a cross-linking group represented by formula (XL-1), formula (XL-16) or formula (XL-17), particularly preferably a cross-linking group represented by formula (XL-1) or formula (XL-17), and particularly preferably a cross-linking group represented by formula (XL-17).

[0629] As the cross-linking group represented by X, from the perspective of better external quantum efficiency of the light-emitting element of the present invention and better cross-linking properties of the polymer compound of the second organic layer, it is preferably a cross-linking group represented by formula (XL-2) to (XL-4), formula (XL-7) to (XL-10), formula (XL-14), formula (XL-15) or formula (XL-17), more preferably a cross-linking group represented by formula (XL-9), formula (XL-10) or formula (XL-17), and particularly preferably a cross-linking group represented by formula (XL-17).

[0630] From the perspective of excellent stability and cross-linking properties of the polymer compound of the second organic layer, the structural unit represented by formula (2) is preferably in an amount of 0.5 to 80 mol %, more preferably 3 to 65 mol %, and further preferably 5 to 50 mol % relative to the total amount of the structural units contained in the polymer compound of the second organic layer.

[0631] The polymer compound of the second organic layer may contain only one type of the structural unit represented by the formula (2), or may contain two or more types of the structural unit represented by the formula (2).

[0632] When the polymer compound of the second organic layer contains two or more structural units represented by formula (2), it is preferred that the crosslinking groups represented by X of at least two structural units of the structural units represented by formula (2) are different from each other. The preferred range of the combination of crosslinking groups represented by different Xs is the same as the preferred range of the combination of the above-mentioned different crosslinking groups.

[0633] The structural unit represented by formula (2')

[0634] From the viewpoint of further improving the external quantum efficiency of the light-emitting element of the present invention, mA is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, further preferably 0 or 1, and particularly preferably 0.

[0635] From the viewpoint of further improving the external quantum efficiency of the light-emitting element of the present invention, m is preferably 1 or 2, and more preferably 2.

[0636] From the viewpoint that the polymer compound of the second organic layer can be easily produced and the external quantum efficiency of the light-emitting device of the present invention is more excellent, c is preferably 0.

[0637] From the viewpoint that the external quantum efficiency of the light-emitting element of the present invention is more excellent, Ar 5 An aromatic hydrocarbon group which may have a substituent is preferred.

[0638] Ar 5 The definition and examples of the arylene moiety of the aromatic hydrocarbon group after removing m substituents are similar to those of Ar in formula (X). X2 The definitions and examples of the arylene group shown are the same.

[0639] Ar 5 The definition and examples of the divalent heterocyclic group portion after removing m substituents from the heterocyclic group shown are the same as those of Ar in formula (X): X2 The definitions and examples of the divalent heterocyclic moiety shown are the same.

[0640] Ar 5 Definitions and examples of divalent groups of a group formed by direct bonding of at least one aromatic hydrocarbon ring and at least one heterocyclic ring after removing m substituents are similar to those of Ar in formula (X).X2 The definitions and 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 are the same as those shown above.

[0641] From the viewpoint that the external quantum efficiency of the light-emitting element of the present invention is more excellent, Ar 4 and Ar 6 An arylene group which may have a substituent is preferred.

[0642] Ar 4 and Ar 6 The definitions and examples of the arylene group shown are similar to those of Ar in formula (X). X1 and Ar X3 The definitions and examples of the arylene group shown are the same.

[0643] Ar 4 and Ar 6 The definitions and examples of the divalent heterocyclic group shown are similar to those of Ar in formula (X). X1 and Ar X3 The definitions and examples of the divalent heterocyclic group shown are the same.

[0644] Ar 4 ,Ar 5 and Ar 6 Examples and preferred ranges of substituents that the groups shown in the table may optionally have are similar to those of Ar Y1 The examples and preferred ranges of the substituents which the groups shown in the figure may have are the same as those of the group shown in the figure. 4 ,Ar 5 and Ar 6 Examples and preferred ranges of substituents that may be further possessed by the substituents that the groups represented by Y1 Examples and preferred ranges of substituents that may be further possessed by the substituents that the groups shown above may have are the same as those of the substituents that may be further possessed by the groups shown above.

[0645] K A The definitions and examples of the alkylene group, cycloalkylene group, arylene group, and divalent heterocyclic group shown in the figure are the same as those of L A The definitions and examples of the alkylene group, cycloalkylene group, arylene group and divalent heterocyclic group are the same as those shown.

[0646] From the perspective of facilitating the production of the polymer compound of the second organic layer, K A It is preferably an arylene group or an alkylene group, more preferably a phenylene group, a fluorenediyl group or an alkylene group, further preferably a phenylene group or a methylene group, and these groups may have a substituent.

[0647] K A Examples and preferred ranges of substituents that the groups shown in the table may optionally have are similar to those of L AExamples and preferred ranges of substituents that the groups shown may have are the same.

[0648] K A Examples and preferred ranges of substituents that may be further possessed by the substituents that the groups represented by Y1 Examples and preferred ranges of substituents that may be further possessed by the substituents that the groups shown above may have are the same as those of the substituents that may be further possessed by the groups shown above.

[0649] The definition and examples of the crosslinking group represented by X' are the same as the definition and examples of the crosslinking group represented by X described above.

[0650] From the perspective of excellent stability of the polymer compound of the second organic layer and excellent cross-linking properties of the polymer compound of the second organic layer, the total amount of the structural unit represented by formula (2′) relative to the total amount of the structural units contained in the polymer compound of the second organic layer is preferably 0.5 to 50 mol%, more preferably 3 to 30 mol%, and further preferably 5 to 20 mol%.

[0651] The polymer compound of the second organic layer may contain only one type of the structural unit represented by the formula (2'), or may contain two or more types of the structural unit represented by the formula (2').

[0652] When the polymer compound of the second organic layer contains two or more structural units represented by formula (2'), it is preferred that the crosslinking groups represented by X' of at least two structural units of the structural units represented by formula (2') are different from each other. The preferred range of the combination of crosslinking groups represented by different X' is the same as the preferred range of the combination of the above-mentioned different crosslinking groups.

[0653] Preferred forms of the structural unit represented by formula (2) or (2′)

[0654] Examples of the structural unit represented by formula (2) include structural units represented by formula (2-1) to formula (2-30), and examples of the structural unit represented by formula (2') include structural units represented by formula (2'-1) to formula (2'-9). Among them, from the perspective of excellent crosslinking of the polymer compound of the second organic layer, structural units represented by formula (2-1) to formula (2-30) are preferred, structural units represented by formula (2-1) to formula (2-15), formula (2-19), formula (2-20), formula (2-23), formula (2-25) or formula (2-30) are more preferred, and structural units represented by formula (2-1) to formula (2-9) or formula (2-30) are still more preferred.

[0655] [Chemistry 97]

[0656]

[0657] [Chemistry 98]

[0658]

[0659] [Chemistry 99]

[0660]

[0661] Other structural units

[0662] From the perspective of excellent hole transport properties, the polymer compound of the second organic layer preferably further comprises a structural unit represented by formula (X). In addition, from the perspective of further improving the external quantum efficiency of the light-emitting element of the present invention, the polymer compound of the second organic layer preferably further comprises a structural unit represented by formula (Y).

[0663] From the viewpoint of excellent hole transport properties and further excellent external quantum efficiency of the light-emitting device of the present invention, the polymer compound of the second organic layer preferably further includes a structural unit represented by formula (X) and a structural unit represented by formula (Y).

[0664] The definition and examples of the structural unit represented by the formula (X) which may be contained in the polymer compound of the second organic layer are the same as the definition and examples of the structural unit represented by the formula (X) which may be contained in the above-mentioned polymer host.

[0665] When the polymer compound of the second organic layer includes the structural unit represented by formula (X), Ar is preferably selected from the viewpoint of increasing the energy level of the lowest triplet excited state of the polymer compound of the second organic layer. X1 and Ar X3 At least one of them is a group represented by formula (X-1-1′), formula (X-1-1″), formula (X-1-2′), formula (X-1-2″) or formula (X-2-1) to formula (X-2-4), more preferably a group represented by formula (X-1-1′), formula (X-1-1″), formula (X-1-2′), formula (X-2-2) or formula (X-2-3), further preferably a group represented by formula (X-1-1′), formula (X-1-1″) or formula (X-1-2′), and particularly preferably a group represented by formula (X-1-1″).

[0666] When the polymer compound of the second organic layer includes the structural unit represented by formula (X), Ar X1 and Ar X3Preferred are groups represented by formula (X-1-1′), formula (X-1-1″), formula (X-1-2′), formula (X-1-2″) or formulas (X-2-1) to (X-2-4); more preferred are groups represented by formula (X-1-1′), formula (X-1-1″), formula (X-1-2′), formula (X-2-2) or formula (X-2-3); further preferred are groups represented by formula (X-1-1′), formula (X-1-1″) or formula (X-1-2′); and particularly preferred are groups represented by formula (X-1-1″).

[0667] [Chemical 100]

[0668]

[0669] [Chemistry 101]

[0670]

[0671] [Where R Y1 , R Y11 and X Y1 Means the same as above.]

[0672] The definition and examples of the structural unit represented by formula (Y) which may be contained in the polymer compound of the second organic layer are the same as the definition and examples of the structural unit represented by formula (Y) which may be contained in the above-mentioned polymer host.

[0673] When the polymer compound of the second organic layer contains a structural unit represented by formula (Y), from the viewpoint that the energy level of the lowest triplet excited state of the polymer compound of the second organic layer becomes higher, it is preferably a structural unit represented by formula (Y-1-1), formula (Y-1-2), formula (Y-2-1) to (Y-2-4), or formula (Y-Y3-1) to formula (Y-Y3-4), more preferably a structural unit represented by formula (Y-1-1′), formula (Y-1-1″), formula (Y-1-2′), formula (Y-1-2″), formula (Y-2-2), formula (Y-2-3), or formula (Y-Y3-1) to formula (Y-Y3-3), further preferably a structural unit represented by formula (Y-1-1′), formula (Y-1-1″), formula (Y-1-2′), formula (Y-2-3), or formula (Y-Y3-1), and particularly preferably a structural unit represented by formula (Y-1-1′), formula (Y-1-1″), formula (Y-1-2′), formula (Y-2-3), or formula (Y-Y3-1). - 1′).

[0674] When the polymer compound of the second organic layer contains a structural unit represented by formula (Y), it is preferred to contain a structural unit represented by any one of formulas (Y-8) to (Y-10), and it is more preferred to contain a structural unit represented by formula (Y-10), from the perspective that the energy level of the lowest triplet excited state of the polymer compound of the second organic layer becomes higher and the hole transport property of the polymer compound of the second organic layer becomes better.

[0675] The polymer compound of the second organic layer may contain only one structural unit represented by formula (X) or two or more structural units represented by formula (X). The polymer compound of the second organic layer may contain only one structural unit represented by formula (Y) or two or more structural units represented by formula (Y).

[0676] When the polymer compound of the second organic layer contains a structural unit represented by formula (X), from the perspective of excellent hole transport properties, the total amount of the structural unit represented by formula (X) relative to the structural units contained in the polymer compound of the second organic layer is preferably 0.1 to 90 mol%, more preferably 1 to 70 mol%, and further preferably 10 to 50 mol%.

[0677] The polymer compound in the second organic layer comprises a structural unit represented by formula (Y), and the structural unit represented by formula (Y) is Ar Y1 In the case of a structural unit of an arylene group, the total amount of the structural unit contained in the polymer compound of the second organic layer is preferably 0.5 to 90 mol %, more preferably 30 to 60 mol % from the viewpoint of better external quantum efficiency of the light-emitting element of the present invention.

[0678] The polymer compound in the second organic layer comprises a structural unit represented by formula (Y), and the structural unit represented by formula (Y) is Ar Y1 In the case of a structural unit which is a divalent heterocyclic group, or a divalent group formed by direct bonding of at least one arylene group and at least one divalent heterocyclic group, from the perspective of excellent charge transport properties of the polymer compound of the second organic layer, the total amount of the structural unit contained in the polymer compound of the second organic layer is preferably 0.1 to 90 mol %, more preferably 1 to 70 mol %, and further preferably 10 to 50 mol %.

[0679] Examples of the polymer compound of the second organic layer include polymer compounds P-7 to P-14. Here, "other structural units" refer to structural units other than the structural units represented by formula (2), formula (2'), formula (X) and formula (Y).

[0680] [Table 2]

[0681]

[0682] [In the table, p', q', r', s' and t' represent the molar ratio of each structural unit. p'+q'+r'+s'+t'=100, and 70≤p'+q'+r'+s'≤100.]

[0683] The polymer compound of the second organic layer may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, and may be in other forms, but is preferably a copolymer obtained by copolymerizing a plurality of raw material monomers.

[0684] The polystyrene-equivalent number average molecular weight of the polymer compound of the second organic layer is preferably 5×10 3 ~1×10 6 , more preferably 1×10 4 ~5×10 5 , more preferably 1.5×10 4 ~1×10 5 .

[0685] [Method for producing polymer compound of second organic layer]

[0686] The polymer compound of the second organic layer can be produced by the same method as the above-mentioned method for producing the polymer host.

[0687] [Second composition]

[0688] The second organic layer can be a layer containing a crosslinked polymer compound comprising the second organic layer and a composition (hereinafter also referred to as "second composition") of at least one material selected from a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material and an antioxidant.

[0689] Examples and preferred ranges of the hole transport material, electron transport material, hole injection material and electron injection material contained in the second composition are the same as those contained in the first composition.

[0690] Examples of the light-emitting material contained in the second composition include the fluorescent light-emitting material optionally contained in the first composition and a phosphorescent metal complex having iridium, platinum or europium as a central metal. The light-emitting material may be used alone or in combination of two or more.

[0691] In the second composition, the amount of each of the hole transport material, electron transport material, hole injection material, electron injection material and light emitting material is usually 1 to 400 parts by mass, preferably 5 to 150 parts by mass, based on 100 parts by mass of the crosslinked polymer compound of the second organic layer.

[0692] Examples and preferred ranges of the antioxidant contained in the second composition are the same as those in the first composition. In the second composition, the amount of the antioxidant is usually 0.001 to 10 parts by mass, based on 100 parts by mass of the crosslinked polymer compound of the second organic layer.

[0693] The composition of the polymer compound and the solvent containing the second organic layer (hereinafter also referred to as "second ink") can be suitably used in the wet method described in the first ink. The preferred range of the viscosity of the second ink is the same as the preferred range of the viscosity of the first ink. Examples and preferred ranges of the solvent contained in the second ink are the same as those of the solvent contained in the first ink.

[0694] In the second ink, the amount of the solvent blended is usually 1,000 to 100,000 parts by mass, preferably 2,000 to 20,000 parts by mass, based on 100 parts by mass of the polymer compound of the second organic layer.

[0695] <Layer structure of light-emitting element>

[0696] The light-emitting element of the present invention may have layers other than the anode, the cathode, the first organic layer, and the second organic layer.

[0697] In the light-emitting element of the present invention, the first organic layer is generally a light-emitting layer (hereinafter referred to as “first light-emitting layer”).

[0698] In the light-emitting element of the present invention, the second organic layer is generally a hole transport layer, a second light-emitting layer or an electron transport layer, preferably a hole transport layer or a second light-emitting layer, and more preferably a hole transport layer.

[0699] In the light-emitting element of the present invention, it is preferred that the first organic layer and the second organic layer are adjacent to each other in terms of further improving the external quantum efficiency of the light-emitting element of the present invention.

[0700] In the light-emitting element of the present invention, from the perspective of better external quantum efficiency of the light-emitting element of the present invention, the second organic layer is preferably a layer arranged between the anode and the first organic layer, more preferably a hole transport layer or a second light-emitting layer arranged between the anode and the first organic layer, and further preferably a hole transport layer arranged between the anode and the first organic layer.

[0701] The first organic layer of the light-emitting element of the present invention may contain a single compound (T) or two or more compounds (T). The second organic layer of the light-emitting element of the present invention may contain a single cross-linked polymer compound of the second organic layer or two or more cross-linked polymer compounds of the second organic layer.

[0702] In the light-emitting element of the present invention, when the second organic layer is a hole transport layer disposed between the anode and the first organic layer, from the aspect that the external quantum efficiency of the light-emitting element of the present invention is more excellent, it is preferred to further include a hole injection layer between the anode and the second organic layer. When the second organic layer is a hole transport layer disposed between the anode and the first organic layer, from the aspect that the external quantum efficiency of the light-emitting element of the present invention is more excellent, it is preferred to further include at least one of an electron injection layer and an electron transport layer between the cathode and the first organic layer.

[0703] In the light-emitting element of the present invention, when the second organic layer is a second light-emitting layer disposed between the anode and the first organic layer, from the perspective of a better external quantum efficiency of the light-emitting element of the present invention, it is preferred that at least one of a hole injection layer and a hole transport layer is further provided between the anode and the second organic layer. In the case where the second organic layer is a second light-emitting layer disposed between the anode and the first organic layer, from the perspective of a better external quantum efficiency of the light-emitting element of the present invention, it is preferred that at least one of an electron injection layer and an electron transport layer is further provided between the cathode and the first organic layer.

[0704] In the light-emitting element of the present invention, when the second organic layer is a second light-emitting layer disposed between the cathode and the first organic layer, from the perspective of a better external quantum efficiency of the light-emitting element of the present invention, it is preferred that at least one of a hole injection layer and a hole transport layer is further provided between the anode and the first organic layer. In the case where the second organic layer is a second light-emitting layer disposed between the cathode and the first organic layer, from the perspective of a better external quantum efficiency of the light-emitting element of the present invention, it is preferred that at least one of an electron injection layer and an electron transport layer is further provided between the cathode and the second organic layer.

[0705] In the light-emitting element of the present invention, when the second organic layer is an electron transport layer disposed between the cathode and the first organic layer, from the perspective of a better external quantum efficiency of the light-emitting element of the present invention, it is preferred that at least one of a hole injection layer and a hole transport layer is further provided between the anode and the first organic layer. In the case where the second organic layer is an electron transport layer disposed between the cathode and the first organic layer, from the perspective of a better external quantum efficiency of the light-emitting element of the present invention, it is preferred that an electron injection layer is further provided between the cathode and the second organic layer.

[0706] Specific layer structures of the light-emitting element of the present invention include, for example, layer structures shown in (D1) to (D15). The light-emitting element of the present invention usually has a substrate, and layers may be stacked on the substrate starting from an anode or starting from a cathode.

[0707] (D1) anode / second light-emitting layer (second organic layer) / first light-emitting layer (first organic layer) / cathode

[0708] (D2) anode / hole transport layer (second organic layer) / first light-emitting layer (first organic layer) / cathode

[0709] (D3) anode / hole injection layer / second light-emitting layer (second organic layer) / first light-emitting layer (first organic layer) / cathode

[0710] (D4) anode / hole injection layer / second light-emitting layer (second organic layer) / first light-emitting layer (first organic layer) / electron transport layer / cathode

[0711] (D5) anode / hole injection layer / second light-emitting layer (second organic layer) / first light-emitting layer (first organic layer) / electron injection layer / cathode

[0712] (D6) anode / hole injection layer / second light-emitting layer (second organic layer) / first light-emitting layer (first organic layer) / electron transport layer / electron injection layer / cathode

[0713] (D7) anode / hole injection layer / hole transport layer (second organic layer) / first light-emitting layer (first organic layer) / cathode

[0714] (D8) anode / hole injection layer / hole transport layer (second organic layer) / first light-emitting layer (first organic layer) / electron transport layer / cathode

[0715] (D9) anode / hole injection layer / hole transport layer (second organic layer) / first light-emitting layer (first organic layer) / electron injection layer / cathode

[0716] (D10) anode / hole injection layer / hole transport layer (second organic layer) / first light-emitting layer (first organic layer) / electron transport layer / electron injection layer / cathode

[0717] (D11) anode / hole injection layer / hole transport layer / second light-emitting layer (second organic layer) / first light-emitting layer (first organic layer) / electron transport layer / electron injection layer / cathode

[0718] (D12) anode / hole injection layer / hole transport layer (second organic layer) / first light-emitting layer (first organic layer) / second light-emitting layer / electron transport layer / electron injection layer / cathode

[0719] (D13) anode / hole injection layer / hole transport layer / first light-emitting layer (first organic layer) / second light-emitting layer (second organic layer) / electron transport layer / electron injection layer / cathode

[0720] (D14) anode / hole injection layer / hole transport layer / first light-emitting layer (first organic layer) / electron transport layer (second organic layer) / electron injection layer / cathode

[0721] (D15) anode / hole injection layer / hole transport layer (second organic layer) / second light-emitting layer / first light-emitting layer (first organic layer) / electron transport layer / electron injection layer / cathode

[0722] In (D1) to (D15), " / " means that the layers before and after are adjacent and stacked. Specifically, "second light-emitting layer (second organic layer) / first light-emitting layer (first organic layer)" means that the second light-emitting layer (second organic layer) and the first light-emitting layer (first organic layer) are adjacent and stacked.

[0723] From the viewpoint of more excellent external quantum efficiency of the light-emitting element of the present invention, the layer structures represented by (D3) to (D12) are preferred, and the layer structures represented by (D7) to (D10) are more preferred.

[0724] In the light-emitting element of the present invention, two or more layers of each of the anode, the hole injection layer, the hole transport layer, the second light-emitting layer, the electron transport layer, the electron injection layer and the cathode may be provided as necessary.

[0725] When there are a plurality of anodes, hole injection layers, hole transport layers, second light-emitting layers, electron transport layers, electron injection layers and cathodes, they may be the same or different.

[0726] The thickness of the anode, hole injection layer, hole transport layer, first light emitting layer, second light emitting layer, electron transport layer, electron injection layer and cathode is usually 1 nm to 1 μm, preferably 2 nm to 500 nm, more preferably 5 nm to 150 nm.

[0727] In the light-emitting element of the present invention, the order, number and thickness of the stacked layers may be adjusted in consideration of the light-emitting efficiency, driving voltage and element life of the light-emitting element.

[0728] [Second light-emitting layer]

[0729] The second light-emitting layer is usually a layer containing a second organic layer or a light-emitting material, preferably a layer containing a light-emitting material. In the case where the second light-emitting layer is a layer containing a light-emitting material, the light-emitting material contained in the second light-emitting layer may include, for example, a light-emitting material optionally contained in the second composition. The light-emitting material contained in the second light-emitting layer may be contained in a single type, or may be contained in two or more types of light-emitting materials contained in the second light-emitting layer.

[0730] When the light-emitting element of the present invention has a second light-emitting layer, and the hole transport layer and the electron transport layer described below are not the second organic layer, the second light-emitting layer is preferably the second organic layer.

[0731] [Hole Transport Layer]

[0732] The hole transport layer is usually a layer containing a second organic layer or a hole transport material, preferably a second organic layer. In the case where the hole transport layer is a layer containing a hole transport material, examples of hole transport materials include hole transport materials optionally contained in the first composition. The hole transport layer may contain a single hole transport material, or may contain hole transport materials contained in two or more hole transport layers.

[0733] When the light-emitting element of the present invention has a hole transport layer, and the second light-emitting layer and the electron transport layer described later are not the second organic layer, the hole transport layer is preferably the second organic layer.

[0734] [Electron transport layer]

[0735] The electron transport layer is generally a layer containing a second organic layer or an electron transport material, preferably a layer containing an electron transport material. In the case where the electron transport layer is a layer containing an electron transport material, the electron transport material contained in the electron transport layer may include, for example, an electron transport material optionally contained in the above-mentioned first composition. It may contain an electron transport material contained in a single electron transport layer, or it may contain an electron transport material contained in two or more electron transport layers.

[0736] When the light-emitting element of the present invention has an electron transport layer, and the second light-emitting layer and the hole transport layer are not the second organic layer, the electron transport layer is preferably the second organic layer.

[0737] [Hole injection layer and electron injection layer]

[0738] The hole injection layer is a layer containing a hole injection material. As the hole injection material contained in the hole injection layer, for example, the hole injection material optionally contained in the first composition can be cited. The hole injection layer can contain a single hole injection material contained in one type, or can contain hole injection materials contained in two or more types of hole injection layers.

[0739] The electron injection layer is a layer containing an electron injection material. As the electron injection material contained in the electron injection layer, for example, the electron injection material optionally contained in the above-mentioned first composition can be cited. The electron injection material contained in the electron injection layer can be contained alone, or the electron injection material contained in the electron injection layer can be contained in more than two kinds.

[0740] [Substrate / Electrode]

[0741] The substrate in the light-emitting element can be any substrate that can form an electrode and does not undergo chemical changes when forming an organic layer, such as a substrate formed of glass, plastic, silicon, etc. When an opaque substrate is used, it is preferred that the electrode farthest from the substrate is transparent or translucent.

[0742] Examples of materials for the anode include conductive metal oxides, translucent metals, preferably indium oxide, zinc oxide, tin oxide; conductive compounds such as indium tin oxide (ITO) and indium zinc oxide; a composite of silver, palladium and copper (APC); NESA, gold, platinum, silver and copper.

[0743] Examples of cathode materials include metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, zinc, and indium; alloys of two or more of these; alloys of one or more of these with one or more of silver, copper, manganese, titanium, cobalt, nickel, tungsten, and tin; and graphite and graphite intercalation compounds. Examples of alloys include magnesium-silver alloys, magnesium-indium alloys, magnesium-aluminum alloys, indium-silver alloys, lithium-aluminum alloys, lithium-magnesium alloys, lithium-indium alloys, and calcium-aluminum alloys.

[0744] In the light-emitting element of the present invention, at least one of the anode and the cathode is usually transparent or translucent, but the anode is preferably transparent or translucent.

[0745] Examples of the method for forming the anode and the cathode include a vacuum deposition method, a sputtering method, an ion plating method, a plating method, and a lamination method.

[0746] [Method for manufacturing light-emitting element]

[0747] In the light-emitting element of the present invention, as the method for forming each layer such as the first light-emitting layer, the second light-emitting layer, the hole transport layer, the electron transport layer, the hole injection layer, and the electron injection layer, when a low molecular weight compound is used, for example, a vacuum evaporation method using powder, a method based on film formation using a solution or a molten state can be mentioned; when a high molecular weight compound is used, for example, a method based on film formation using a solution or a molten state can be mentioned.

[0748] The first light-emitting layer, the second light-emitting layer, the hole transport layer, the electron transport layer, the hole injection layer and the electron injection layer can be formed by using inks containing the first ink, the second ink and the above-mentioned light-emitting material, hole transport material, electron transport material, hole injection material and electron injection material, respectively, and using a coating method such as spin coating and inkjet printing.

[0749] [Application of light-emitting elements]

[0750] In order to obtain planar light emission using a light-emitting element, it is sufficient to configure the planar anode and cathode in a manner that they overlap. In order to obtain patterned light emission, there are the following methods: a method of providing a mask with a patterned window on the surface of a planar light-emitting element, a method of forming a layer intended to be a non-light-emitting portion extremely thick and substantially non-luminescent, and a method of forming an anode or cathode, or both electrodes in a pattern. By forming a pattern using any of these methods, and configuring a number of electrodes in a manner that can be independently switched (ON / OFF), a segmented display device capable of displaying numbers, text, etc. can be obtained. In order to form a dot matrix display device, the anode and cathode are configured in a manner that forms strips together and is orthogonal. By separately applying a plurality of polymer compounds with different luminescent colors, or by using a color filter or a fluorescence conversion filter, partial color display and multi-color display can be performed. The dot matrix display device can be passively driven, or it can be actively driven in combination with TFT, etc. These display devices can be used for displays of computers, televisions, portable terminals, etc. The planar light-emitting element can be suitably used as a planar light source for backlighting of a liquid crystal display device, or a planar light source for illumination. If a flexible substrate is used, it can also be used as a curved light source or display device.

[0751] Example

[0752] Hereinafter, the present invention will be described in more detail using examples, but the present invention is not limited to these examples.

[0753] In the examples, the polystyrene-equivalent number average molecular weight (Mn) and the polystyrene-equivalent weight average molecular weight (Mw) of the polymer compound were determined by size exclusion chromatography (SEC) using tetrahydrofuran as a mobile phase. The measurement conditions of SEC are as follows.

[0754] The polymer compound to be measured was dissolved in tetrahydrofuran at a concentration of about 0.05 mass %, and 10 μL was injected into the SEC. The mobile phase flowed at a flow rate of 2.0 mL / min. As a chromatographic column, PLgel MIXED-B (manufactured by Polymerlaboratories) was used. A UV-VIS detector (manufactured by Shimadzu Corporation, trade name: SPD-10Avp) was used as the detector.

[0755] LC-MS was measured by the following method.

[0756] The sample was dissolved in chloroform or tetrahydrofuran to a concentration of about 2 mg / mL, and about 1 μL was injected into LC-MS (Agilent, trade name: 1100LCMSD). The mobile phase of LC-MS was acetonitrile and tetrahydrofuran, and the two were used while changing the ratio, and flowed at a flow rate of 0.2 mL / min. The chromatographic column used was L-column 2ODS (3 μm) (manufactured by the Chemical Evaluation Research Institute, inner diameter: 2.1 mm, length: 100 mm, particle size: 3 μm).

[0757] NMR was measured by the following method.

[0758] 5 to 10 mg of the measurement sample is dissolved in about 0.5 mL of deuterated chloroform (CDCl3), deuterated tetrahydrofuran, deuterated dimethyl sulfoxide, deuterated acetone, deuterated N,N-dimethylformamide, deuterated toluene, deuterated methanol, deuterated ethanol, deuterated 2-propanol or deuterated dichloromethane, and the measurement is performed using an NMR apparatus (manufactured by Agilent, trade name: INOVA300 or MERCURY 400VX).

[0759] As an indicator of the purity of the compound, the value of the area percentage of high performance liquid chromatography (HPLC) is used. Unless otherwise specified, the value is based on the value at UV = 254nm of HPLC (manufactured by Shimadzu Corporation, trade name: LC-20A). At this time, the compound to be measured is dissolved in tetrahydrofuran or chloroform in a manner to reach a concentration of 0.01 to 0.2% by mass, and 1 to 10 μL is injected into HPLC according to the concentration. Regarding the mobile phase of HPLC, the ratio of acetonitrile / tetrahydrofuran is changed to 100 / 0 to 0 / 100 (volume ratio) while using both, and flowing at a flow rate of 1.0 mL / min. The chromatographic column uses Kaseisorb LC ODS 2000 (manufactured by Tokyo Chemical Industry Co., Ltd.) or an ODS chromatographic column with equivalent performance. The detector uses a photodiode array detector (manufactured by Shimadzu Corporation, trade name: SPD-M20A).

[0760] About ΔE of Compounds ST The density functional method at the B3LYP level was used to optimize the ground state structure of the compound. At this time, 6-31G* was used as the basis function. Then, Gaussian09 was used as the quantum chemical calculation program to calculate the ΔE of the compound using the time-dependent density functional method at the B3LYP level. ST and oscillator strength.

[0761] The energy level of the lowest triplet excited state of the polymer compound is obtained by measuring the phosphorescence emission spectrum of the polymer compound at 77K.

[0762] Specifically, the polymer compound is dissolved in xylene at a concentration of 3.0% by mass. Using the obtained xylene solution, a film is formed on a glass substrate by a drop casting method, and then vacuum dried at room temperature to form a film of the polymer compound. The glass substrate on which the film of the polymer compound is formed is put into a glass tube under a nitrogen atmosphere set to an oxygen concentration of less than 5ppm, and then the glass tube is sealed. The sealed glass tube is cooled to 77K in liquid nitrogen as a measurement sample. The obtained measurement sample is irradiated with excitation light (excitation wavelength: 325nm), and the phosphorescence emission spectrum of the polymer compound is measured. In the phosphorescence emission spectrum of the obtained polymer compound, the maximum peak wavelength of the shortest wavelength is converted into energy, and the obtained value is used as the energy level of the lowest triplet excited state of the polymer compound.

[0763] In the measurement of the phosphorescence spectrum of the polymer compound, a rotating chopper was used, a He-Cd laser (manufactured by Golden Gate Lightwave Co., Ltd.) was used as an excitation light source, and a multi-channel spectrometer (trade name: PMA-12) manufactured by Hamamatsu Photonics Co., Ltd. was used as a detector.

[0764] <Synthesis Examples T1 and T2> Synthesis of Compounds T1 and T2

[0765] Compound T1 was synthesized according to the method described in International Publication No. 2010 / 136109.

[0766] Compound T2 was synthesized according to the method described in International Publication No. 2007 / 063754.

[0767] [Chemistry 102]

[0768]

[0769] ΔE of compound T1 ST and oscillator strengths are 0.1295 eV and 0.0011 respectively.

[0770] ΔE of compound T2 ST and oscillator strengths are 0.1072eV and 0.0062 respectively.

[0771] <Synthesis Example T3> Synthesis of Compound T3

[0772] [Chemistry 103]

[0773]

[0774] [Chemistry 104]

[0775]

[0776] (Synthesis of Compound T3-3)

[0777] After setting the reaction container to an argon atmosphere, compound T3-1 (2.5 g), compound T3-2 (2.8 g), tris(dibenzylideneacetone)dipalladium (0) (0.25 g), tri-tert-butylphosphonium tetrafluoroborate (0.13 g), sodium tert-butoxide (1.3 g) and toluene (75 mL) were added and stirred at room temperature for 1 hour. After that, hexane and silica gel were added thereto, stirred at 50°C, and filtered with a filter paved with silica gel. The obtained filtrate was concentrated under reduced pressure to obtain a solid. After the obtained solid was purified by silica gel column chromatography (a mixed solvent of hexane and toluene), it was dried under reduced pressure at 50°C to obtain a crude purified product of compound T3-3 (3.1 g, brown oil). Hexane and activated carbon were added to the obtained crude purified product, stirred at room temperature, and then filtered under reduced pressure. The obtained filtrate was concentrated under reduced pressure to obtain compound T3-3 (2.7 g, yellow solid). The HPLC area percentage value of compound T3-3 was 98.5%.

[0778] 1 H-NMR (CDCl3, 400MHz): δ (ppm) = 8.20-8.11 (m, 2H), 7.74-6.85 (m, 26H), 2.50-2.30 (m, 7H), 1.53-0.82 (m, 22H).

[0779] (Synthesis of Compound T3-4)

[0780] After setting the reaction container to a nitrogen atmosphere, compound T3-3 (2.6 g), tetrahydrofuran (26 mL), dimethyl sulfoxide (16 mL) and 33% potassium hydroxide aqueous solution (5.4 g) were added and stirred under reflux for 6.5 hours. After the obtained mixture was cooled to room temperature, it was extracted with a mixed solution of ion exchange water and toluene, and the obtained organic layer was washed with ion exchange water. After the obtained organic layer was dried over anhydrous sodium sulfate, it was filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude purified product. After the obtained crude purified product was purified by silica gel column chromatography (mixed solvent of hexane and toluene), it was dried under reduced pressure at 50°C to obtain compound T3-4 (2.1 g, brown oil). The HPLC area percentage value of compound T3-4 is 97.6%.

[0781] (Synthesis of Compound T3)

[0782] After setting the reaction container to a nitrogen atmosphere, compound T3-4 (2.1 g), compound T3-5 (1.3 g), palladium acetate (0.071 g), tri-tert-butylphosphonium tetrafluoroborate (0.096 g) and xylene (84 mL) were added. After that, sodium tert-butoxide (0.76 g) was added thereto and stirred at 100°C for 1 hour. After the obtained mixture was cooled to room temperature, hexane and silica gel were added, and after stirring at room temperature, it was filtered with a filter paved with silica gel. The obtained filtrate was concentrated under reduced pressure to obtain a crude purified product. The obtained crude purified product was crystallized with a mixed solvent of hexane and ethanol to obtain a solid. The obtained solid was purified by silica gel column chromatography (a mixed solvent of hexane and toluene), and then crystallized with a mixed solvent of toluene, ethyl acetate and acetonitrile. The obtained solid was dried under reduced pressure at 50°C to obtain compound T3 (1.2 g, yellow solid). The HPLC area percentage value of compound T3 is 99.5% or more.

[0783] LC-MS (APCI, positive): m / z=977.5[M+H] +

[0784] 1 H-NMR (CDCl3, 400MHz): δ (ppm) = 9.06-8.98 (m, 2H), 8.82-8.80 (m, 4H), 7.90-6.80 (m, 32H), 2.54-2.43 (m, 4H), 1.53-1.49 (m, 4H), 1.25 (m, 12H), 0.85-0.83 (m, 6H).

[0785] ΔE of compound T3 ST and oscillator strengths are 0.1088eV and 0.1848 respectively.

[0786] <Compounds T4 to T12> Synthesis or acquisition of compounds T4 to T12

[0787] Compounds T4, T5, T6, T7 and T10 were purchased from Luminescense Technology.

[0788] Compound T8 was synthesized according to the method described in International Publication No. 2008 / 056746.

[0789] Compound T9 was synthesized according to the method described in International Publication No. 2006 / 114966.

[0790] Compound T11 was synthesized according to the method described in International Publication No. 2015 / 102118.

[0791] Compound T12 was synthesized according to the method described in JP-A-2010-254676.

[0792] [Chemistry 105]

[0793]

[0794] [Chemistry 106]

[0795]

[0796] [Chemistry 107]

[0797]

[0798] ΔE of compound T4 ST and oscillator strengths are 0.1563 eV and 0.0069 respectively.

[0799] ΔE of compound T5 ST and oscillator strengths are 0.0265eV and 0.0323 respectively.

[0800] ΔE of compound T6 ST and oscillator strengths are 0.0065eV and 0 respectively.

[0801] ΔE of compound T7 ST and oscillator strengths are 0.1185 eV and 0.0574 respectively.

[0802] ΔE of compound T8 ST and oscillator strengths are 0.0659 eV and 0.0007 respectively.

[0803] ΔE of compound T9 ST and oscillator strengths are 0.3215 eV and 0.0448 respectively.

[0804] ΔE of compound T10 ST and oscillator strengths are 0.0102eV and 0 respectively.

[0805] ΔE of compound T11 ST and oscillator strengths are 0.4464eV and 0.4672 respectively.

[0806] ΔE of compound T12 ST and oscillator strengths are 0.5762eV and 0.3640 respectively.

[0807] <Compounds HM-1 and E1> Synthesis or acquisition of compounds HM-1 and E1

[0808] Compound E1 was synthesized according to the method described in International Publication No. 2007 / 058368.

[0809] Compound HM-1 was purchased from Luminescense Technology.

[0810] [Chemical 1081

[0811]

[0812] ΔE of compound HM-1 ST and oscillator strengths are 0.2966 eV and 0.0082 respectively.

[0813] ΔE of compound E1 ST and oscillator strengths are 0.7881eV and 0.1353 respectively.

[0814] <Synthesis Example M> Synthesis of Compounds M1 to M25

[0815] Compound M1 and Compound M3 were synthesized according to the method described in JP-A-2010-189630.

[0816] Compound M2 was synthesized according to the method described in International Publication No. 2012 / 086671.

[0817] Compound M4, Compound M5, Compound M20, and Compound M21 were synthesized according to the method described in International Publication No. 2013 / 191088.

[0818] Compound M6 and Compound M7 were synthesized according to the method described in International Publication No. 2002 / 045184.

[0819] Compound M8 was synthesized according to the method described in International Publication No. 2011 / 049241.

[0820] Compound M9 and Compound M10 were synthesized according to the method described in International Publication No. 2013 / 146806.

[0821] Compound M11 was synthesized according to the method described in International Publication No. 2005 / 049546.

[0822] Compound M12 was synthesized according to the method described in International Publication No. 2015 / 145871.

[0823] Compound M13 was synthesized according to the method described in JP-A-2010-215886.

[0824] Compound M14 was synthesized according to the method described in JP-A-2008-106241.

[0825] Compound M15 was synthesized according to the method described in JP-A-2010-215886.

[0826] Compound M16 and Compound M24 were synthesized according to the method described in International Publication No. 2016 / 031639.

[0827] Compound M17 and Compound M19 were synthesized according to the method described in JP-A-2011-174062.

[0828] Compound M18, Compound M22, and Compound M23 were synthesized according to the method described in International Publication No. 2016 / 031639.

[0829] Compound M25 was synthesized according to the method described in International Publication No. 2002 / 045184.

[0830] [Chemistry 109]

[0831]

[0832] [Chemistry 110]

[0833]

[0834] [Chemistry 111]

[0835]

[0836] [Chemistry 112]

[0837]

[0838] [Chemistry 113]

[0839]

[0840] [Chemistry 114]

[0841]

[0842] [Chemistry 115]

[0843]

[0844] <Synthesis Example HP1> Synthesis of polymer compound HP-1

[0845] The polymer compound HP-1 was synthesized using the compound M1, the compound M2, and the compound M3 according to the method described in Japanese Patent Application Laid-Open No. 2012-036388. The Mn of the polymer compound HP-1 was 9.6×10 4 , Mw is 2.2×10 5 .

[0846] The polymer compound HP-1 is a copolymer composed of structural units derived from the compound M1, structural units derived from the compound M2, and structural units derived from the compound M3 in a molar ratio of 50:40:10 as a theoretical value obtained from the amounts of the charged raw materials.

[0847] <Synthesis Example HP2> Synthesis of polymer compound HP-2

[0848] The polymer compound HP-2 was synthesized using the compound M1, the compound M4, and the compound M5 according to the method described in International Publication No. 2015 / 008851. The Mn of the polymer compound HP-2 was 8.5×10 4 , Mw is 2.2×10 5 .

[0849] The polymer compound HP-2 is a copolymer composed of structural units derived from the compound M1, structural units derived from the compound M4, and structural units derived from the compound M5 in a molar ratio of 50:26:24 as a theoretical value obtained from the amounts of the charged raw materials.

[0850] <Synthesis Example HTL1> Synthesis of polymer compound HTL-1

[0851] The polymer compound HTL-1 was synthesized using the compound M6 and the compound M7 according to the method described in Japanese Patent Application Laid-Open No. 2012-36381. The polystyrene-equivalent number average molecular weight and weight average molecular weight of the polymer compound HTL-1 were Mn=8.1×10 4 and Mw = 3.4 × 10 5 .

[0852] The polymer compound HTL-1 is a copolymer composed of a structural unit derived from the compound M6 and a structural unit derived from the compound M7 at a molar ratio of 50:50 based on a theoretical value obtained from the amounts of the charged raw materials.

[0853] The energy level of the lowest triplet excited state of the polymer compound HTL-1 is 2.16 eV.

[0854] <Synthesis Example HTL2> Synthesis of polymer compound HTL-2

[0855] The polymer compound HTL-2 was synthesized using compound M19, compound M11, compound M25, and compound M15 according to the method described in Japanese Patent Application Laid-Open No. 2012-144722. The Mn of the polymer compound HTL-2 was 5.0×10 4 , Mw is 2.5×10 5 .

[0856] The polymer compound HTL-2 is a copolymer composed of structural units derived from compound M19, structural units derived from compound M11, structural units derived from compound M25, and structural units derived from compound M15 in a molar ratio of 50:30:12.5:7.5 as a theoretical value obtained from the amounts of input raw materials.

[0857] The energy level of the lowest triplet excited state of the polymer compound HTL-2 is 2.16 eV.

[0858] <Synthesis Example HTL3> Synthesis of polymer compound HTL-3

[0859] The polymer compound HTL-3 was synthesized using the compound M1 and the compound M11 according to the method described in International Publication No. 2015 / 194448. The polystyrene-equivalent number average molecular weight and weight average molecular weight of the polymer compound HTL-3 were Mn=4.5×10 4 and Mw = 1.5 × 10 5 .

[0860] The polymer compound HTL-3 is a copolymer composed of a structural unit derived from the compound M1 and a structural unit derived from the compound M11 at a molar ratio of 50:50 based on a theoretical value obtained from the amounts of the charged raw materials.

[0861] The energy level of the lowest triplet excited state of the polymer compound HTL-3 is 2.33 eV.

[0862] <Synthesis Example HTL4> Synthesis of polymer compound HTL-4

[0863] The polymer compound HTL-4 was synthesized using compound M1, compound M11, and compound M8 according to the method described in International Publication No. 2013 / 146806. The Mn of the polymer compound HTL-4 was 1.9×10 4 , Mw is 9.9×10 4 .

[0864] The polymer compound HTL-4 is a copolymer composed of structural units derived from the compound M1, structural units derived from the compound M11, and structural units derived from the compound M8 in a molar ratio of 50:42.5:7.5 as a theoretical value obtained from the amounts of the input raw materials.

[0865] The energy level of the lowest triplet excited state of the polymer compound HTL-4 is 2.33 eV.

[0866] <Synthesis Example HTL5> Synthesis of polymer compound HTL-5

[0867] (Step 1) After the interior of the reaction container was set to an inert gas atmosphere, Compound M9 (1.07 g), Compound M10 (0.198 g), Compound M7 (0.919 g), bis(tri(2-methoxyphenyl)phosphine)palladium dichloride (1.8 mg) and toluene (50 ml) were added and heated to 100°C.

[0868] (Step 2) A 20% by mass tetraethylammonium hydroxide aqueous solution (8.7 ml) was added dropwise to the obtained reaction solution, and the mixture was refluxed for 6 hours.

[0869] (Step 3) Thereafter, 2-ethylphenylboric acid (60.0 mg), a 20% by mass tetraethylammonium hydroxide aqueous solution (8.7 ml) and bis(tri(2-methoxyphenyl)phosphine)palladium dichloride (1.8 mg) were added thereto, and the mixture was refluxed for 16 hours.

[0870] (Step 4) After that, add an aqueous solution of sodium diethyldithiocarbamate thereto, and stir at 80°C for 2 hours. After cooling the obtained reaction solution, wash it twice with 3.6% by mass hydrochloric acid, twice with 2.5% by mass ammonia solution, and then wash it 6 times with water. When the obtained solution is added dropwise to methanol, a precipitate is generated. The obtained precipitate is dissolved in toluene, and passed through an alumina column and a silica gel column in sequence to purify it. When the obtained solution is added dropwise to methanol and stirred, a precipitate is generated. The obtained precipitate is filtered and dried to obtain 1.14 g of the polymer compound HTL-5. The Mn of the polymer compound HTL-5 is 3.6×10 4 , Mw is 2.0×10 5 .

[0871] The polymer compound HTL-5 is a copolymer composed of structural units derived from the compound M9, structural units derived from the compound M10, and structural units derived from the compound M7 in a molar ratio of 40:10:50 as a theoretical value obtained from the amounts of the input raw materials.

[0872] The energy level of the lowest triplet excited state of the polymer compound HTL-5 is 2.46 eV.

[0873] <Synthesis Example HTL6> Synthesis of polymer compound HTL-6

[0874] The polymer compound HTL-6 was synthesized using compound M12, compound M10, and compound M24 according to the method described in International Publication No. 2015 / 145871. The Mn of the polymer compound HTL-6 is 2.8×10 4 , Mw is 1.1×10 5 .

[0875] The polymer compound HTL-6 is a copolymer composed of structural units derived from the compound M12, structural units derived from the compound M10, and structural units derived from the compound M24 in a molar ratio of 40:10:50 as a theoretical value obtained from the amounts of the input raw materials.

[0876] The energy level of the lowest triplet excited state of the polymer compound HTL-6 is 2.69 eV.

[0877] <Synthesis Example HTL7> Synthesis of polymer compound HTL-7

[0878] The polymer compound HTL-7 was synthesized using compound M1, compound M13, compound M14, and compound M15 according to the method described in International Publication No. 2016 / 031639. The Mn of the polymer compound HTL-7 is 2.4×10 4 , Mw is 1.7×10 5 .

[0879] The polymer compound HTL-7 is a copolymer composed of structural units derived from compound M1, structural units derived from compound M13, structural units derived from compound M14, and structural units derived from compound M15 in a molar ratio of 50:40:5:5 as a theoretical value obtained from the amounts of input raw materials.

[0880] The energy level of the lowest triplet excited state of the polymer compound HTL-7 is 2.49 eV.

[0881] <Synthesis Example HTL8> Synthesis of polymer compound HTL-8

[0882] (Step 1) After setting the interior of the reaction container to an inert gas atmosphere, compound M1 (0.995 g), compound M7 (0.736 g), compound M14 (0.106 g), compound M15 (0.0924 g), bis(tri(2-methoxyphenyl)phosphine)palladium dichloride (1.8 mg) and toluene (50 ml) were added and heated to 105°C.

[0883] (Step 2) A 20% by mass tetraethylammonium hydroxide aqueous solution (6.6 ml) was added dropwise to the obtained reaction solution, and the mixture was refluxed for 5.5 hours.

[0884] (Step 3) Thereafter, phenylboric acid (24.4 mg), a 20% by mass tetraethylammonium hydroxide aqueous solution (6.6 ml) and bis(tri(2-methoxyphenyl)phosphine)palladium dichloride (1.8 mg) were added thereto, and the mixture was refluxed for 14 hours.

[0885] (Step 4) After that, an aqueous solution of sodium diethyldithiocarbamate is added thereto, and the mixture is stirred at 80°C for 2 hours. After the obtained reaction solution is cooled, it is washed twice with water, washed twice with a 3% by mass aqueous solution of acetic acid, and washed twice with water. When the obtained solution is added dropwise to methanol, a precipitate is generated. The obtained precipitate is dissolved in toluene, and the solution is passed through an alumina column and a silica gel column in sequence for purification. When the obtained solution is added dropwise to methanol and stirred, a precipitate is generated. The obtained precipitate is filtered and dried to obtain 0.91 g of the polymer compound HTL-8. The Mn of the polymer compound HTL-8 is 5.2×10 4 , Mw is 2.5×10 5 .

[0886] The polymer compound HTL-8 is a copolymer composed of structural units derived from compound M1, structural units derived from compound M7, structural units derived from compound M14, and structural units derived from compound M15 in a molar ratio of 50:40:5:5 according to a theoretical value obtained from the amounts of input raw materials.

[0887] The energy level of the lowest triplet excited state of the polymer compound HTL-8 is 2.45 eV.

[0888] <Synthesis Example HTL9> Synthesis of polymer compound HTL-9

[0889] The polymer compound HTL-9 was synthesized using compound M16, compound M17, compound M14, and compound M15 according to the method described in International Publication No. 2016 / 125560. The Mn of the polymer compound HTL-9 is 3.5×10 4 , Mw is 1.6×10 5 .

[0890] The polymer compound HTL-9 is a copolymer composed of structural units derived from compound M16, structural units derived from compound M17, structural units derived from compound M14, and structural units derived from compound M15 in a molar ratio of 50:40:5:5 as a theoretical value obtained from the amounts of input raw materials.

[0891] The energy level of the lowest triplet excited state of the polymer compound HTL-9 is 2.39 eV.

[0892] <Synthesis Example HTL10> Synthesis of polymer compound HTL-10

[0893] The polymer compound HTL-10 was synthesized using compound M18, compound M17, compound M14, and compound M15 according to the method described in International Publication No. 2016 / 031639. The Mn of the polymer compound HTL-10 was 5.3×10 4 , Mw is 2.0×10 5 .

[0894] The polymer compound HTL-10 is a copolymer composed of structural units derived from compound M18, structural units derived from compound M17, structural units derived from compound M14, and structural units derived from compound M15 in a molar ratio of 50:40:5:5 as a theoretical value obtained from the amounts of input raw materials.

[0895] The energy level of the lowest triplet excited state of the polymer compound HTL-10 is 2.37 eV.

[0896] <Synthesis Example HTL11> Synthesis of polymer compound HTL-11

[0897] The polymer compound HTL-11 was synthesized using compound M19, compound M20, compound M21, and compound M22 according to the method described in International Publication No. 2016 / 031639. The Mn of the polymer compound HTL-11 was 5.1×10 4 , Mw is 2.0×10 5 .

[0898] The polymer compound HTL-11 is a copolymer composed of structural units derived from compound M19, structural units derived from compound M20, structural units derived from compound M21, and structural units derived from compound M22 in a molar ratio of 40:5:5:50 according to a theoretical value obtained from the amounts of input raw materials.

[0899] The energy level of the lowest triplet excited state of the polymer compound HTL-11 is 2.33 eV.

[0900] <Synthesis Example HTL12> Synthesis of polymer compound HTL-12

[0901] The polymer compound HTL-12 was synthesized using compound M23, compound M17, compound M14, and compound M15 according to the method described in International Publication No. 2016 / 125560. The Mn of the polymer compound HTL-12 is 5.2×10 4 , Mw is 2.2×10 5 .

[0902] The polymer compound HTL-12 is a copolymer composed of structural units derived from compound M23, structural units derived from compound M17, structural units derived from compound M14, and structural units derived from compound M15 in a molar ratio of 50:40:5:5 as a theoretical value obtained from the amounts of input raw materials.

[0903] The energy level of the lowest triplet excited state of the polymer compound HTL-12 is 2.33 eV.

[0904] <Synthesis Example HTL13> Synthesis of polymer compound HTL-13

[0905] The polymer compound HTL-13 was synthesized using compound M12, compound M10, and compound M11 according to the method described in International Publication No. 2015 / 145871. The Mn of the polymer compound HTL-13 was 2.3×10 4 , Mw is 1.2×10 5 .

[0906] The polymer compound HTL-13 is a copolymer composed of structural units derived from the compound M12, structural units derived from the compound M10, and structural units derived from the compound M11 in a molar ratio of 45:5:50 based on a theoretical value obtained from the amounts of the input raw materials.

[0907] The energy level of the lowest triplet excited state of the polymer compound HTL-13 is 2.33 eV.

[0908] <Example D1> Fabrication and Evaluation of Light Emitting Element D1

[0909] (Formation of Anode and Hole Injection Layer)

[0910] An ITO film was applied to a glass substrate by sputtering with a thickness of 45 nm to form an anode. On the anode, ND-3202 (manufactured by Nissan Chemical Industries, Ltd.) was formed as a hole injection material by spin coating with a thickness of 50 nm. The hole injection layer was formed by heating at 50° C. for 3 minutes and then at 230° C. for 15 minutes in an atmospheric atmosphere.

[0911] (Formation of the Second Organic Layer)

[0912] The polymer compound HTL-5 was dissolved in xylene at a concentration of 0.6 mass %. The obtained xylene solution was used to form a film with a thickness of 20 nm on the hole injection layer by spin coating, and heated on a hot plate at 200° C. for 30 minutes under a nitrogen atmosphere to form a second organic layer. The polymer compound HTL-5 was converted into a cross-linked body by heating.

[0913] (Formation of the First Organic Layer)

[0914] The polymer compound HP-1 and the compound T3 (polymer compound HP-1 / compound T3=85 mass% / 15 mass%) were dissolved in xylene at a concentration of 1.8 mass%. The obtained xylene solution was used to form a film with a thickness of 70 nm on the second organic layer by spin coating, and heated at 130° C. for 10 minutes under a nitrogen atmosphere to form a first organic layer.

[0915] (Formation of cathode)

[0916] The substrate with the first organic layer formed thereon was depressurized to 1.0×10 -4 Pa or less, sodium fluoride of about 4 nm was vapor-deposited on the first organic layer as a cathode, and then aluminum of about 80 nm was vapor-deposited on the sodium fluoride layer. After vapor deposition, the layer was sealed using a glass substrate, thereby manufacturing a light-emitting element D1.

[0917] (Evaluation of Light Emitting Element)

[0918] By applying voltage to the light emitting element D1, EL light emission is observed. 2 The external quantum efficiency under the condition is 12.0[%], and the CIE chromaticity coordinates (x, y) = (0.29, 0.57).

[0919] <Example D2> Fabrication and evaluation of light-emitting element D2

[0920] Light-emitting element D2 was prepared in the same manner as in Example D1 except that "High molecular compound HP-2" was used instead of "High molecular compound HP-1" in Example D1 (Formation of the first organic layer). EL light emission was observed by applying voltage to light-emitting element D2. 2 The external quantum efficiency is 14.2[%], and the CIE chromaticity coordinates (x, y) = (0.27, 0.56).

[0921] <Example D3> Fabrication and evaluation of light-emitting element D3

[0922] Light-emitting element D3 was prepared in the same manner as in Example D1, except that "the polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3=85 mass% / 15 mass%) were dissolved in xylene at a concentration of 1.8 mass%" in Example D1 (Formation of the first organic layer) and "the compound HM-1 and compound T3 (compound HM-1 / compound T3=85 mass% / 15 mass%) were dissolved in toluene at a concentration of 2 mass%". A voltage was applied to the light-emitting element D3, thereby observing EL light emission. At 2 mA / cm 2The external quantum efficiency under the condition is 11.3[%], and the CIE chromaticity coordinates (x, y) = (0.31, 0.57).

[0923] <Example D4> Preparation and evaluation of light-emitting element D4

[0924] In Example D1 (Formation of the first organic layer), "polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3=85 mass% / 15 mass%) were dissolved in xylene at a concentration of 1.8 mass%" was replaced by "compound HM-1 and compound T3 (compound HM-1 / compound T3=85 mass% / 15 mass%) were dissolved in toluene at a concentration of 2 mass%". In addition, "polymer compound HTL-4" was used instead of "polymer compound HTL-5" in Example D1 (Formation of the second organic layer). Light-emitting element D4 was prepared in the same manner as in Example D1. EL light emission was observed by applying voltage to light-emitting element D4. At 2 mA / cm 2 The external quantum efficiency is 7.4[%], and the CIE chromaticity coordinates (x, y) = (0.31, 0.58).

[0925] <Comparative Example CD1> Preparation and Evaluation of Light Emitting Element CD1

[0926] In Example D1 (Formation of the first organic layer), "polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3=85 mass% / 15 mass%) were dissolved in xylene at a concentration of 1.8 mass%" was replaced by "compound HM-1 and compound T3 (compound HM-1 / compound T3=85 mass% / 15 mass%) were dissolved in toluene at a concentration of 2 mass%". In addition, "polymer compound HTL-3" was used instead of "polymer compound HTL-5" in Example D1 (Formation of the second organic layer). Light-emitting element CD1 was prepared in the same manner as in Example D1. EL light emission was observed by applying voltage to light-emitting element CD1. At 2 mA / cm 2 The external quantum efficiency is 4.6[%], and the CIE chromaticity coordinates (x, y) = (0.31, 0.58).

[0927] <Comparative Example CD2> Preparation and Evaluation of Light Emitting Element CD2

[0928] In Example D1 (Formation of the first organic layer), "polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3=85 mass% / 15 mass%) were dissolved in xylene at a concentration of 1.8 mass%" was replaced by "compound HM-1 and compound T3 (compound HM-1 / compound T3=85 mass% / 15 mass%) were dissolved in toluene at a concentration of 2 mass%". In addition, "polymer compound HTL-1" was used instead of "polymer compound HTL-5" in Example D1 (Formation of the second organic layer). Light-emitting element CD2 was prepared in the same manner as in Example D1. EL light emission was observed by applying voltage to light-emitting element CD2. At 2 mA / cm 2 The external quantum efficiency is 2.3[%], and the CIE chromaticity coordinates (x, y) = (0.31, 0.57).

[0929] [Table 3]

[0930]

[0931] <Example D5> Preparation and evaluation of light-emitting element D5

[0932] Instead of "dissolving polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3=85 mass% / 15 mass%) in xylene at a concentration of 1.8 mass%" in Example D1 (Formation of the first organic layer), "dissolving compound HM-1 and compound T3 (compound HM-1 / compound T3=85 mass% / 15 mass%) in toluene at a concentration of 2 mass%" was used. Also, instead of "polymer compound HTL-5" in Example D1 (Formation of the second organic layer), "polymer compound HTL-6" was used. Except for this, the light-emitting element D5 was prepared in the same manner as in Example D1.

[0933] By applying voltage to the light emitting element D5, EL light emission was observed. 2 The external quantum efficiency is 7.2[%], and the CIE chromaticity coordinates (x, y) = (0.32, 0.57).

[0934] <Example D6> Preparation and evaluation of light-emitting element D6

[0935] A light-emitting element D6 was prepared in the same manner as in Example D5, except that "polymer compound HTL-7" was used instead of "polymer compound HTL-6" in Example D5 (Formation of the second organic layer).

[0936] By applying voltage to the light emitting element D6, EL light emission was observed. 2The external quantum efficiency under the condition is 11.1 [%], and the CIE chromaticity coordinates (x, y) = (0.30, 0.56).

[0937] <Example D7> Fabrication and evaluation of light-emitting element D7

[0938] A light-emitting element D7 was prepared in the same manner as in Example D5, except that "polymer compound HTL-5" was used instead of "polymer compound HTL-6" in Example D5 (Formation of the second organic layer).

[0939] By applying voltage to the light emitting element D7, EL light emission was observed. 2 The external quantum efficiency is 12.4[%], and the CIE chromaticity coordinates (x, y) = (0.32, 0.57).

[0940] <Example D8> Preparation and evaluation of light-emitting element D8

[0941] A light-emitting element D8 was prepared in the same manner as in Example D5, except that "polymer compound HTL-8" was used instead of "polymer compound HTL-6" in Example D5 (Formation of the second organic layer).

[0942] By applying voltage to the light emitting element D8, EL light emission was observed. 2 The external quantum efficiency under the condition is 10.6[%], and the CIE chromaticity coordinates (x, y) = (0.31, 0.57).

[0943] <Example D9> Preparation and evaluation of light-emitting element D9

[0944] A light-emitting element D9 was prepared in the same manner as in Example D5, except that "polymer compound HTL-9" was used instead of "polymer compound HTL-6" in Example D5 (Formation of the second organic layer).

[0945] By applying voltage to the light emitting element D9, EL light emission was observed. 2 The external quantum efficiency is 8.6[%], and the CIE chromaticity coordinates (x, y) = (0.32, 0.57).

[0946] <Example D10> Preparation and evaluation of light-emitting element D10

[0947] A light-emitting element D10 was prepared in the same manner as in Example D5, except that "polymer compound HTL-10" was used instead of "polymer compound HTL-6" in Example D5 (Formation of the second organic layer).

[0948] By applying voltage to the light emitting element D10, EL light emission was observed. 2 The external quantum efficiency is 8.7[%], and the CIE chromaticity coordinates (x, y) = (0.31, 0.57).

[0949] <Example D11> Preparation and evaluation of light-emitting element D11

[0950] A light-emitting element D11 was prepared in the same manner as in Example D5, except that "polymer compound HTL-4" was used instead of "polymer compound HTL-6" in Example D5 (Formation of the second organic layer).

[0951] By applying voltage to the light emitting element D11, EL light emission was observed. 2 The external quantum efficiency is 8.0[%], and the CIE chromaticity coordinates (x, y) = (0.32, 0.58).

[0952] <Example D12> Preparation and evaluation of light-emitting element D12

[0953] A light-emitting element D12 was prepared in the same manner as in Example D5, except that "polymer compound HTL-11" was used instead of "polymer compound HTL-6" in Example D5 (Formation of the second organic layer).

[0954] By applying voltage to the light emitting element D12, EL light emission was observed. 2 The external quantum efficiency is 7.3[%], and the CIE chromaticity coordinates (x, y) = (0.32, 0.57).

[0955] <Example D13> Preparation and evaluation of light-emitting element D13

[0956] A light-emitting element D13 was prepared in the same manner as in Example D5, except that "polymer compound HTL-12" was used instead of "polymer compound HTL-6" in Example D5 (Formation of the second organic layer).

[0957] By applying voltage to the light emitting element D13, EL light emission was observed. 2 The external quantum efficiency is 7.9[%], and the CIE chromaticity coordinates (x, y) = (0.31, 0.58).

[0958] <Comparative Example CD3> Preparation and Evaluation of Light Emitting Element CD3

[0959] A light-emitting element CD3 was prepared in the same manner as in Example D5, except that "polymer compound HTL-3" was used instead of "polymer compound HTL-6" in Example D5 (Formation of the second organic layer).

[0960] By applying voltage to the light emitting element CD3, EL light emission was observed. 2 The external quantum efficiency is 4.7[%], and the CIE chromaticity coordinates (x, y) = (0.32, 0.58).

[0961] <Comparative Example CD4> Preparation and Evaluation of Light Emitting Element CD4

[0962] A light-emitting element CD4 was prepared in the same manner as in Example D5, except that "polymer compound HTL-2" was used instead of "polymer compound HTL-6" in Example D5 (Formation of the second organic layer).

[0963] By applying voltage to the light emitting element CD4, EL light emission was observed. 2 The external quantum efficiency is 4.2[%], and the CIE chromaticity coordinates (x, y) = (0.31, 0.57).

[0964] <Comparative Example CD5> Preparation and Evaluation of Light Emitting Element CD5

[0965] A light-emitting element CD5 was prepared in the same manner as in Example D5, except that "polymer compound HTL-1" was used instead of "polymer compound HTL-6" in Example D5 (Formation of the second organic layer).

[0966] By applying voltage to the light emitting element CD5, EL light emission was observed. 2 The external quantum efficiency is 2.3[%], and the CIE chromaticity coordinates are (x, y)=(0.31, 0.58).

[0967] [Table 4]

[0968]

[0969] <Example D14> Preparation and evaluation of light-emitting element D14

[0970] Instead of "dissolving polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3=85 mass% / 15 mass%) in xylene at a concentration of 1.8 mass%" in Example D1 (Formation of the first organic layer), "dissolving compound HM-1, compound T1 and compound E1 (compound HM-1 / compound T1 / compound E1=75 mass% / 15 mass% / 10 mass%) in chlorobenzene at a concentration of 2.6 mass%" was used. In addition, instead of "polymer compound HTL-5" in Example D1 (Formation of the second organic layer), "polymer compound HTL-13" was used. Except for this, light-emitting element D14 was prepared in the same manner as in Example D1.

[0971] By applying voltage to the light emitting element D14, EL light emission was observed. 2 The external quantum efficiency under the condition is 3.9[%], and the CIE chromaticity coordinates (x, y) = (0.29, 0.63).

[0972] <Example D15> Preparation and evaluation of light-emitting element D15

[0973] Instead of "dissolving polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3=85 mass% / 15 mass%) in xylene at a concentration of 1.8 mass%" in Example D1 (Formation of the first organic layer), "dissolving compound HM-1, compound T1 and compound E1 (compound HM-1 / compound T1 / compound E1=75 mass% / 15 mass% / 10 mass%) in chlorobenzene at a concentration of 2.6 mass%" was used. Also, instead of "polymer compound HTL-5" in Example D1 (Formation of the second organic layer), "polymer compound HTL-4" was used. Except for this, light-emitting element D15 was prepared in the same manner as in Example D1.

[0974] By applying voltage to the light emitting element D15, EL light emission was observed. 2 The external quantum efficiency is 3.8[%], and the CIE chromaticity coordinates (x, y) = (0.29, 0.63).

[0975] <Example D16> Preparation and evaluation of light-emitting element D16

[0976] Light-emitting element D16 is prepared in the same manner as in Example D14, except that "Compound HM-1, Compound T2 and Compound E1 (Compound HM-1 / Compound T2 / Compound E1=75 mass% / 15 mass% / 10 mass%)" is used instead of "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1=75 mass% / 15 mass% / 10 mass%)" in Example D14 (Formation of the first organic layer).

[0977] By applying voltage to the light emitting element D16, EL light emission was observed. 2 The external quantum efficiency is 5.2[%], and the CIE chromaticity coordinates (x, y) = (0.29, 0.63).

[0978] <Example D17> Preparation and evaluation of light-emitting element D17

[0979] Light-emitting element D17 is prepared in the same manner as in Example D15, except that "Compound HM-1, Compound T2 and Compound E1 (Compound HM-1 / Compound T2 / Compound E1=75 mass% / 15 mass% / 10 mass%)" is used instead of "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1=75 mass% / 15 mass% / 10 mass%)" in Example D15 (Formation of the first organic layer).

[0980] By applying voltage to the light emitting element D17, EL light emission was observed. 2 The external quantum efficiency is 4.6[%], and the CIE chromaticity coordinates (x, y) = (0.29, 0.63).

[0981] <Example D18> Preparation and evaluation of light-emitting element D18

[0982] Light-emitting element D18 is prepared in the same manner as in Example D14, except that "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1=75 mass% / 15 mass% / 10 mass%)" is used instead of "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1=75 mass% / 15 mass% / 10 mass%)" in Example D14 (Formation of the first organic layer).

[0983] By applying voltage to the light emitting element D18, EL light emission was observed. 2 The external quantum efficiency is 4.6[%], and the CIE chromaticity coordinates (x, y) = (0.29, 0.64).

[0984] <Example D19> Preparation and evaluation of light-emitting element D19

[0985] Light-emitting element D19 is prepared in the same manner as in Example D15, except that "Compound HM-1, Compound T4 and Compound E1 (Compound HM-1 / Compound T4 / Compound E1 = 75 mass % / 15 mass % / 10 mass %)" is used instead of "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1 = 75 mass % / 15 mass % / 10 mass %)" in Example D15 (Formation of the first organic layer).

[0986] By applying voltage to the light emitting element D19, EL light emission was observed. 2 The external quantum efficiency is 3.7[%], and the CIE chromaticity coordinates (x, y) = (0.29, 0.63).

[0987] <Example D20> Preparation and evaluation of light-emitting element D20

[0988] The light-emitting element D20 is prepared in the same manner as in Example D14, except that "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1=75 mass% / 15 mass% / 10 mass%)" is used instead of "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1=75 mass% / 15 mass% / 10 mass%)" in Example D14 (Formation of the first organic layer).

[0989] By applying voltage to the light emitting element D20, EL light emission was observed. 2 The external quantum efficiency under the condition is 6.0[%], and the CIE chromaticity coordinates (x, y) = (0.31, 0.62).

[0990] <Example D21> Preparation and evaluation of light-emitting element D21

[0991] The light-emitting element D21 is prepared in the same manner as in Example D15, except that "Compound HM-1, Compound T3 and Compound E1 (Compound HM-1 / Compound T3 / Compound E1 = 75 mass % / 15 mass % / 10 mass %)" is used instead of "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1 = 75 mass % / 15 mass % / 10 mass %)" in Example D15 (Formation of the first organic layer).

[0992] By applying voltage to the light emitting element D21, EL light emission was observed. 2 The external quantum efficiency is 4.7[%], and the CIE chromaticity coordinates (x, y) = (0.31, 0.62).

[0993] <Example D22> Preparation and evaluation of light-emitting element D22

[0994] The light-emitting element D22 is prepared in the same manner as in Example D14, except that "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1=75 mass% / 15 mass% / 10 mass%)" is used instead of "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1=75 mass% / 15 mass% / 10 mass%)" in Example D14 (Formation of the first organic layer).

[0995] By applying voltage to the light emitting element D22, EL light emission was observed. 2 The external quantum efficiency under the condition is 8.1[%], and the CIE chromaticity coordinates (x, y) = (0.32, 0.61).

[0996] <Example D23> Preparation and evaluation of light-emitting element D23

[0997] The light-emitting element D23 is prepared in the same manner as in Example D14, except that "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1=75 mass% / 15 mass% / 10 mass%)" is used instead of "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1=75 mass% / 15 mass% / 10 mass%)" in Example D14 (Formation of the first organic layer).

[0998] By applying voltage to the light emitting element D23, EL light emission was observed. 2 The external quantum efficiency is 9.8[%], and the CIE chromaticity coordinates (x, y) = (0.32, 0.60).

[0999] <Example D24> Preparation and evaluation of light-emitting element D24

[1000] The light-emitting element D24 is prepared in the same manner as in Example D15, except that "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1=75 mass% / 15 mass% / 10 mass%)" is used instead of "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1=75 mass% / 15 mass% / 10 mass%)" in Example D15 (Formation of the first organic layer).

[1001] By applying voltage to the light emitting element D24, EL light emission was observed. 2 The external quantum efficiency is 7.5[%], and the CIE chromaticity coordinates (x, y) = (0.31, 0.60).

[1002] <Example D25> Preparation and evaluation of light-emitting element D25

[1003] Except that "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1=75 mass% / 15 mass% / 10 mass%)" are used instead of "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1=75 mass% / 15 mass% / 10 mass%)" in Example D14 (Formation of the first organic layer), and that "Polymer compound HTL-5" is used instead of "Polymer compound HTL-13" in Example D14 (Formation of the second organic layer), the light-emitting element D25 is prepared in the same manner as in Example D14.

[1004] By applying voltage to the light emitting element D25, EL light emission was observed. 2 The external quantum efficiency under the condition is 12.1[%], and the CIE chromaticity coordinates (x, y) = (0.32, 0.59).

[1005] <Example D26> Preparation and evaluation of light-emitting element D26

[1006] Instead of using "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1=75 mass% / 15 mass% / 10 mass%)" in Example D14 (Formation of the first organic layer), "Compound HM-1, Compound T3 and Compound E1 (Compound HM-1 / Compound T3 / Compound E1=84 mass% / 15 mass% / 1 mass%)" and instead of using "Polymer Compound HTL-13" in Example D14 (Formation of the second organic layer), "Polymer Compound HTL-6" was used. Except for this, the light-emitting element D26 was prepared in the same manner as in Example D14.

[1007] By applying voltage to the light emitting element D26, EL light emission was observed. 2 The external quantum efficiency is 6.3[%], and the CIE chromaticity coordinates (x, y) = (0.32, 0.59).

[1008] <Example D27> Preparation and evaluation of light-emitting element D27

[1009] The light-emitting element D27 is prepared in the same manner as in Example D14, except that "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1=75 mass% / 15 mass% / 10 mass%)" is used instead of "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1=75 mass% / 15 mass% / 10 mass%)" in Example D14 (Formation of the first organic layer).

[1010] By applying voltage to the light emitting element D27, EL light emission was observed. 2 The external quantum efficiency is 3.7[%], and the CIE chromaticity coordinates (x, y) = (0.29, 0.63).

[1011] <Example D28> Preparation and evaluation of light-emitting element D28

[1012] The light-emitting element D28 is prepared in the same manner as in Example D15, except that "Compound HM-1, Compound T5 and Compound E1 (Compound HM-1 / Compound T5 / Compound E1=75 mass% / 15 mass% / 10 mass%)" is used instead of "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1=75 mass% / 15 mass% / 10 mass%)" in Example D15 (Formation of the first organic layer).

[1013] By applying voltage to the light emitting element D28, EL light emission was observed. 2 The external quantum efficiency under the condition is 3.2[%], and the CIE chromaticity coordinates (x, y) = (0.29, 0.64).

[1014] <Example D29> Preparation and evaluation of light-emitting element D29

[1015] The light-emitting element D29 is prepared in the same manner as in Example D14, except that "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1=75 mass% / 15 mass% / 10 mass%)" is used instead of "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1=75 mass% / 15 mass% / 10 mass%)" in Example D14 (Formation of the first organic layer).

[1016] By applying voltage to the light emitting element D29, EL light emission was observed. 2 The external quantum efficiency is 3.8[%], and the CIE chromaticity coordinates (x, y) = (0.29, 0.63).

[1017] <Example D30> Preparation and evaluation of light-emitting element D30

[1018] The light-emitting element D30 is prepared in the same manner as in Example D14, except that "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1=75 mass% / 15 mass% / 10 mass%)" is used instead of "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1=75 mass% / 15 mass% / 10 mass%)" in Example D14 (Formation of the first organic layer).

[1019] By applying voltage to the light emitting element D30, EL light emission was observed. 2 The external quantum efficiency is 4.8[%], and the CIE chromaticity coordinates (x, y) = (0.29, 0.63).

[1020] <Example D31> Preparation and evaluation of light-emitting element D31

[1021] The light-emitting element D31 is prepared in the same manner as in Example D15, except that "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1=75 mass% / 15 mass% / 10 mass%)" is used instead of "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1=75 mass% / 15 mass% / 10 mass%)" in Example D15 (Formation of the first organic layer).

[1022] By applying voltage to the light emitting element D31, EL light emission was observed. 2 The external quantum efficiency under the condition is 4.1[%], and the CIE chromaticity coordinates (x, y) = (0.29, 0.63).

[1023] <Comparative Example CD6> Preparation and Evaluation of Light-Emitting Element CD6

[1024] Instead of using "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1=75 mass% / 15 mass% / 10 mass%)" in Example D14 (Formation of the first organic layer), "Compound HM-1, Compound T6 and Compound E1 (Compound HM-1 / Compound T6 / Compound E1=75 mass% / 15 mass% / 10 mass%)" and instead of using "Polymer Compound HTL-13" in Example D14 (Formation of the second organic layer), "Polymer Compound HTL-3" was used. Except for this, the light-emitting element CD6 was prepared in the same manner as in Example D14.

[1025] By applying voltage to the light emitting element CD6, EL light emission was observed. 2 The external quantum efficiency is 1.6[%], and the CIE chromaticity coordinates (x, y) = (0.29, 0.62).

[1026] [Table 5]

[1027]

[1028] <Example D32> Fabrication and evaluation of light-emitting element D32

[1029] The light-emitting element D32 is prepared in the same manner as in Example D1, except that the step of "dissolving the polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3=85 mass% / 15 mass%) in xylene at a concentration of 1.8 mass%" is replaced by "dissolving the compound HM-1 and compound T7 (compound HM-1 / compound T7=85 mass% / 15 mass%) in chlorobenzene at a concentration of 2 mass%".

[1030] By applying voltage to the light emitting element D32, EL light emission was observed. 2 The external quantum efficiency is 5.0[%], and the CIE chromaticity coordinates (x, y) = (0.32, 0.59).

[1031] <Comparative Example CD7> Preparation and Evaluation of Light-Emitting Element CD7

[1032] Instead of "dissolving polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3=85 mass% / 15 mass%) in xylene at a concentration of 1.8 mass%" in Example D1 (Formation of the first organic layer), "dissolving compound HM-1 and compound T7 (compound HM-1 / compound T7=85 mass% / 15 mass%) in chlorobenzene at a concentration of 2 mass%" was used. Also, instead of "polymer compound HTL-5" in Example D1 (Formation of the second organic layer), "polymer compound HTL-2" was used. Except for this, the light-emitting element CD7 was prepared in the same manner as in Example D1.

[1033] By applying voltage to the light emitting element CD7, EL light emission was observed. 2 The external quantum efficiency under the condition is 0.8[%], and the CIE chromaticity coordinates (x, y) = (0.32, 0.57).

[1034] [Table 6]

[1035]

[1036] <Example D33> Fabrication and evaluation of light-emitting element D33

[1037] The light-emitting element D33 is prepared in the same manner as in Example D1, except that "polymer compound HP-2 and compound T9 (polymer compound HP-2 / compound T9 = 85 mass % / 15 mass %)" is used instead of "polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3 = 85 mass % / 15 mass %)" in Example D1 (Formation of the first organic layer).

[1038] By applying voltage to the light emitting element D33, EL light emission was observed. 2 The external quantum efficiency is 1.7[%], and the CIE chromaticity coordinates (x, y) = (0.24, 0.41).

[1039] <Example D34> Preparation and evaluation of light-emitting element D34

[1040] The light-emitting element D34 is prepared in the same manner as in Example D1, except that "polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3=85 mass% / 15 mass%)" is used instead of "polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3=85 mass% / 15 mass%)" in Example D1 (Formation of the first organic layer).

[1041] By applying voltage to the light emitting element D34, EL light emission was observed. 2 The external quantum efficiency is 1.7[%], and the CIE chromaticity coordinates (x, y) = (0.24, 0.40).

[1042] <Example D35> Preparation and evaluation of light-emitting element D35

[1043] The light-emitting element D35 is prepared in the same manner as in Example D1, except that "polymer compound HP-2 and compound T10 (polymer compound HP-2 / compound T10 = 85 mass % / 15 mass %)" is used instead of "polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3 = 85 mass % / 15 mass %)" in Example D1 (Formation of the first organic layer).

[1044] By applying voltage to the light emitting element D35, EL light emission was observed. 2 The external quantum efficiency is 3.4[%], and the CIE chromaticity coordinates (x, y) = (0.17, 0.31).

[1045] <Example D36> Preparation and evaluation of light-emitting element D36

[1046] The light-emitting element D36 is prepared in the same manner as in Example D1, except that "polymer compound HP-2 and compound T6 (polymer compound HP-2 / compound T6 = 85 mass % / 15 mass %)" is used instead of "polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3 = 85 mass % / 15 mass %)" in Example D1 (Formation of the first organic layer).

[1047] By applying voltage to the light emitting element D36, EL light emission was observed. 2 The external quantum efficiency is 4.3[%], and the CIE chromaticity coordinates (x, y) = (0.18, 0.36).

[1048] <Example D37> Preparation and evaluation of light-emitting element D37

[1049] Light-emitting element D37 is prepared in the same manner as in Example D1, except that "polymer compound HP-2 and compound T6 (polymer compound HP-2 / compound T6 = 85 mass % / 15 mass %)" are used instead of "polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3 = 85 mass % / 15 mass %)" in Example D1 (Formation of the first organic layer); and "polymer compound HTL-4" is used instead of "polymer compound HTL-5" in Example D1 (Formation of the second organic layer).

[1050] By applying voltage to the light emitting element D37, EL light emission was observed. 2 The external quantum efficiency is 2.4[%], and the CIE chromaticity coordinates (x, y) = (0.24, 0.40).

[1051] <Example D38> Preparation and evaluation of light-emitting element D38

[1052] The light-emitting element D38 is prepared in the same manner as in Example D1, except that "polymer compound HP-1 and compound T5 (polymer compound HP-1 / compound T5 = 85 mass % / 15 mass %)" is used instead of "polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3 = 85 mass % / 15 mass %)" in Example D1 (Formation of the first organic layer).

[1053] By applying voltage to the light emitting element D38, EL light emission was observed. 2 The external quantum efficiency is 1.8[%], and the CIE chromaticity coordinates (x, y) = (0.24, 0.47).

[1054] <Example D39> Preparation and evaluation of light-emitting element D39

[1055] The light-emitting element D39 is prepared in the same manner as in Example D1, except that "polymer compound HP-2 and compound T1 (polymer compound HP-2 / compound T1 = 85 mass % / 15 mass %)" is used instead of "polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3 = 85 mass % / 15 mass %)" in Example D1 (Formation of the first organic layer).

[1056] By applying voltage to the light emitting element D39, EL light emission was observed. 2 The external quantum efficiency under the condition is 3.3[%], and the CIE chromaticity coordinates (x, y) = (0.24, 0.46).

[1057] <Example D40> Preparation and evaluation of light-emitting element D40

[1058] The light-emitting element D40 is prepared in the same manner as in Example D1, except that "polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3=85 mass% / 15 mass%)" is used instead of "polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3=85 mass% / 15 mass%)" in Example D1 (Formation of the first organic layer).

[1059] By applying voltage to the light emitting element D40, EL light emission was observed. 2 The external quantum efficiency is 2.7[%], and the CIE chromaticity coordinates (x, y) = (0.24, 0.47).

[1060] <Example D41> Preparation and evaluation of light-emitting element D41

[1061] The light-emitting element D41 is prepared in the same manner as in Example D1, except that the step of "dissolving the polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3=85 mass% / 15 mass%) in xylene at a concentration of 1.8 mass%" is replaced by "dissolving the compound HM-1 and compound T9 (compound HM-1 / compound T9=85 mass% / 15 mass%) in toluene at a concentration of 2 mass%".

[1062] By applying voltage to the light emitting element D41, EL light emission was observed. 2 The external quantum efficiency is 1.2 [%], and the CIE chromaticity coordinates (x, y) = (0.17, 0.24).

[1063] <Example D42> Preparation and evaluation of light-emitting element D42

[1064] The light-emitting element D42 is prepared in the same manner as in Example D1, except that the step of "dissolving the polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3=85 mass% / 15 mass%) in xylene at a concentration of 1.8 mass%" is replaced by "dissolving the compound HM-1 and compound T1 (compound HM-1 / compound T1=85 mass% / 15 mass%) in toluene at a concentration of 2 mass%".

[1065] By applying voltage to the light emitting element D42, EL light emission was observed. 2The external quantum efficiency is 1.5[%], and the CIE chromaticity coordinates (x, y) = (0.26, 0.47).

[1066] <Example D43> Preparation and evaluation of light-emitting element D43

[1067] The light-emitting element D43 is prepared in the same manner as in Example D1, except that the step of "dissolving the polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3=85 mass% / 15 mass%) in xylene at a concentration of 1.8 mass%" is adopted instead of "dissolving the polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3=85 mass% / 15 mass%) in xylene at a concentration of 1.8 mass%" in Example D1 (Formation of the first organic layer).

[1068] By applying voltage to the light emitting element D43, EL light emission was observed. 2 The external quantum efficiency is 2.1 [%], and the CIE chromaticity coordinates (x, y) = (0.18, 0.27).

[1069] <Example D44> Preparation and evaluation of light-emitting element D44

[1070] Light-emitting element D44 is prepared in the same manner as in Example D1, except that the step of "dissolving polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3=85 mass% / 15 mass%) in xylene at a concentration of 1.8 mass%" is replaced by "dissolving compound HM-1 and compound T11 (compound HM-1 / compound T11=85 mass% / 15 mass%) in toluene at a concentration of 2 mass%".

[1071] By applying voltage to the light emitting element D44, EL light emission was observed. 2 The external quantum efficiency is 2.8[%], and the CIE chromaticity coordinates (x, y) = (0.14, 0.09).

[1072] <Example D45> Preparation and evaluation of light-emitting element D45

[1073] Instead of "dissolving polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3=85 mass% / 15 mass%) in xylene at a concentration of 1.8 mass%" in Example D1 (Formation of the first organic layer), "dissolving compound HM-1 and compound T11 (compound HM-1 / compound T11=85 mass% / 15 mass%) in toluene at a concentration of 2 mass%" was used. Also, instead of "polymer compound HTL-5" in Example D1 (Formation of the second organic layer), "polymer compound HTL-13" was used. Except for this, the light-emitting element D45 was prepared in the same manner as in Example D1.

[1074] By applying voltage to the light emitting element D45, EL light emission was observed. 2 The external quantum efficiency is 5.5[%], and the CIE chromaticity coordinates (x, y) = (0.14, 0.09).

[1075] <Example D46> Preparation and evaluation of light-emitting element D46

[1076] Instead of "dissolving polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3=85 mass% / 15 mass%) in xylene at a concentration of 1.8 mass%" in Example D1 (Formation of the first organic layer), "dissolving compound HM-1 and compound T11 (compound HM-1 / compound T11=85 mass% / 15 mass%) in toluene at a concentration of 2 mass%" was used. Also, instead of "polymer compound HTL-5" in Example D1 (Formation of the second organic layer), "polymer compound HTL-4" was used. Except for this, the light-emitting element D46 was prepared in the same manner as in Example D1.

[1077] By applying a voltage to the light emitting element D46 , thus EL luminescence was observed. At 0.75 mA / cm 2 The external quantum efficiency is 4.4[%], and the CIE chromaticity coordinates (x, y) = (0.14, 0.09).

[1078] <Example D47> Preparation and evaluation of light-emitting element D47

[1079] Light-emitting element D47 is prepared in the same manner as in Example D1, except that "polymer compound HP-2 and compound T11 (polymer compound HP-2 / compound T11 = 85 mass % / 15 mass %)" are used instead of "polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3 = 85 mass % / 15 mass %)" in Example D1 (Formation of the first organic layer); and "polymer compound HTL-7" is used instead of "polymer compound HTL-5" in Example D1 (Formation of the second organic layer).

[1080] By applying voltage to the light emitting element D47, EL light emission was observed. 2 The external quantum efficiency is 6.3[%], and the CIE chromaticity coordinates (x, y) = (0.14, 0.22).

[1081] <Example D48> Preparation and evaluation of light-emitting element D48

[1082] The light-emitting element D48 is prepared in the same manner as in Example D1, except that "polymer compound HP-2 and compound T11 (polymer compound HP-2 / compound T11 = 85 mass % / 15 mass %)" is used instead of "polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3 = 85 mass % / 15 mass %)" in Example D1 (Formation of the first organic layer).

[1083] By applying voltage to the light emitting element D48, EL light emission was observed. 2 The external quantum efficiency is 6.6[%], and the CIE chromaticity coordinates (x, y) = (0.15, 0.26).

[1084] <Example D49> Preparation and evaluation of light-emitting element D49

[1085] Light-emitting element D49 is prepared in the same manner as in Example D1, except that "polymer compound HP-2 and compound T11 (polymer compound HP-2 / compound T1] = 85 mass % / 15 mass %)" are used instead of "polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3 = 85 mass % / 15 mass %)" in Example D1 (Formation of the first organic layer); and "polymer compound HTL-4" is used instead of "polymer compound HTL-5" in Example D1 (Formation of the second organic layer).

[1086] By applying voltage to the light emitting element D49, EL light emission was observed. 2The external quantum efficiency is 8.6[%], and the CIE chromaticity coordinates (x, y) = (0.15, 0.28).

[1087] <Comparative Example CD8> Preparation and Evaluation of Light-Emitting Element CD8

[1088] Instead of "dissolving polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3=85 mass% / 15 mass%) in xylene at a concentration of 1.8 mass%" in Example D1 (Formation of the first organic layer), "dissolving compound HM-1 and compound T1 (compound HM-1 / compound T1=85 mass% / 15 mass%) in toluene at a concentration of 2 mass%" was used. Also, instead of "polymer compound HTL-5" in Example D1 (Formation of the second organic layer), "polymer compound HTL-2" was used. Except for this, the light-emitting element CD8 was prepared in the same manner as in Example D1.

[1089] By applying voltage to the light emitting element CD8, EL light emission was observed. 2 The external quantum efficiency under the condition is 0.7[%], and the CIE chromaticity coordinates (x, y) = (0.20, 0.30).

[1090] <Comparative Example CD9> Preparation and Evaluation of Light-Emitting Element CD9

[1091] Instead of "dissolving polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3=85 mass% / 15 mass%) in xylene at a concentration of 1.8 mass%" in Example D1 (Formation of the first organic layer), "dissolving compound HM-1 and compound T1 (compound HM-1 / compound T1=85 mass% / 15 mass%) in toluene at a concentration of 2 mass%" was used. Also, instead of "polymer compound HTL-5" in Example D1 (Formation of the second organic layer), "polymer compound HTL-3" was used. Except for this, the light-emitting element CD9 was prepared in the same manner as in Example D1.

[1092] By applying voltage to the light emitting element CD9, EL light emission was observed. 2 The external quantum efficiency is 0.5[%], and the CIE chromaticity coordinates (x, y) = (0.31, 0.48).

[1093] <Comparative Example CD10> Preparation and Evaluation of Light Emitting Element CD10

[1094] The light-emitting element CD10 is prepared in the same manner as in Example D1, except that "polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3=85 mass% / 15 mass%)" is used instead of "polymer compound HP-1 and compound T3 (polymer compound HP-1 / compound T3=85 mass% / 15 mass%)" in Example D1 (Formation of the first organic layer).

[1095] By applying voltage to the light emitting element CD10, EL light emission was observed. 2 The external quantum efficiency under the condition is 0.7[%], and the CIE chromaticity coordinates (x, y) = (0.19, 0.21).

[1096] [Table 7]

[1097]

[1098] Industrial Applicability

[1099] According to the present invention, a light-emitting element having excellent external quantum efficiency and a composition useful for producing the light-emitting element can be provided.

Claims

1. A composition comprising: A compound T having an absolute value of a difference between an energy level of the lowest triplet excited state and an energy level of the lowest singlet excited state of 0.5 eV or less; and A polymer compound comprising a structural unit represented by formula (Y), and does not contain phosphorescent metal complexes, In formula (Y), Ar Y1 It 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 may have a substituent.

2. The composition according to claim 1, wherein The compound T is a compound represented by formula (T-1), In formula (T-1), n T1 represents an integer greater than or equal to 0 and less than or equal to 5. T1 In the case of , they are optionally the same or different, Ar T1 represents an aryl group, a substituted amino group or a monovalent heterocyclic group, which may have a substituent. T1 In the case of, they are optionally the same or different, and optionally directly bonded or bonded via a divalent group to form a ring, wherein at least one Ar T1 is a substituted amino group, or contains a nitrogen atom having no double bond in the ring and does not contain a group represented by =N- in the ring, a boron atom, -C(=Z T1 )-, -S(=O)-, -S(=O)2-, and a monovalent heterocyclic group represented by formula (P), Z T1 represents an oxygen atom, a sulfur atom or =N(R ZT1 ) shown in the group, R ZT1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent, L T1 represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, -N(R T1 ')-, oxygen atom or sulfur atom, these groups may have substituents, R T1 ' represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, which may have a substituent. T1 In the case of , they are optionally the same or different, and optionally bonded directly or via a divalent group to form a ring, Ar T2 is a boron atom, -C(=Z T1 )-, a group represented by -S(=O)-, a group represented by -S(=O)2-, a group represented by the above formula (P), an aromatic hydrocarbon group having an electron-withdrawing group, or a heterocyclic group containing a group represented by =N- in the ring, and these groups may have a substituent, n T2 represents an integer of 1 to 15, wherein in Ar T2 When it is a boron atom or a group represented by the formula (P), n T2 is 3, in Ar T2 =Z T1 In the case of a group represented by -S(=O)-, a group represented by -S(=O)-, or a group represented by -S(=O)2-, n T2 is 2, Ar T1 With L T1 Ar is optionally directly bonded or bonded via a divalent group to form a ring. T2 With L T1 Ar is optionally directly bonded or bonded via a divalent group to form a ring. T1 with Ar T2 They may be bonded directly or via a divalent group to form a ring.

3. The composition according to claim 2, wherein At least one of the Ar T1 is a group represented by formula (T1-1), In formula (T1-1), Ring R T1 and Ring R T2 Each independently represents that the ring does not contain -C (=Z T1 )-, or an aromatic hydrocarbon ring containing no group represented by =N-, a boron atom, -C(=Z T1 )-, -S(=O)-, -S(=O)2-, and a heterocyclic ring of a group represented by the formula (P), wherein these rings may have a substituent, Z T1 Means the same as above, X T1 represents a single bond, oxygen atom, sulfur atom, -N(R XT1 )- or -C(R XT1 ')2-, R XT1 and R XT1 ' each independently represents 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, a halogen atom or a cyano group, and these groups may optionally have a substituent. XT1 ' are optionally the same or different, optionally bonded to each other and together with the carbon atoms to which they are bonded to form a ring, R XT1 and Ring R T1 The optional substituents, R XT1 and Ring R T2 The optional substituents, R XT1 ′ and ring R T1 The optional substituents, and R XT1 ′ and ring R T2 The substituents optionally possessed are respectively bonded directly or via a divalent group, and are optionally bonded to form a ring together with the atoms to which they are respectively bonded.

4. The composition according to claim 3, wherein The group represented by formula (T1-1) is a group represented by formula (T1-1A), a group represented by formula (T1-1B), a group represented by formula (T1-1C) or a group represented by formula (T1-1D), In the formula, X T1 Means the same as above, X T2 and X T3 each independently represents a single bond, an oxygen atom, a sulfur atom, -N(R XT2 )- or -C(R XT2 ')2-, R XT2 and R XT2 ' each independently represents 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, a halogen atom or a cyano group, and these groups may optionally have a substituent. XT2 ' are optionally the same or different, optionally bonded directly or via a divalent group and together with the carbon atom to which they are bonded form a ring, R T1 , R T2 , R T3 , R T4 , R T5 , R T6 , R T7 , R T8 , R T9 , R T10 , R T11 and R T12 each independently represents 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, a halogen atom or a cyano group, and these groups may have a substituent, R T1 With R T2 , R T2 With R T3 , R T3 With R T4 , R T5 With R T6 , R T6 With R T7 , R T7 With R T8 , R T9 With R T10 , R T10 With R T11 , and R T11 With R T12 Optionally, they are each directly bonded or bonded via a divalent group and together with the carbon atom to which they are respectively bonded, form a ring.

5. The composition according to any one of claims 2 to 4, wherein The Ar T2 It is a heterocyclic group containing a group represented by =N- in the ring, and the group may have a substituent.

6. The composition according to claim 5, wherein The Ar T2 It is a group obtained by removing one or more hydrogen atoms directly bonded to atoms constituting the ring from a diazole ring, a triazole ring, an oxadiazole ring, a thiadiazole ring, a thiazole ring, an oxazole ring, an isothiazole ring, an isoxazole ring, a benzodiazole ring, a benzotriazole ring, a benzoxadiazole ring, a benzothiadiazole ring, a benzothiazole ring, a benzoxazole ring, an azacarbazole ring, a diazacarbazole ring, a pyridine ring, a diazobenzene ring, a triazine ring, a naphthyrazine ring, a naphthyrazine ring, a triazine ring, a tetraazine ring, an azaanthracene ring, a diazaanthracene ring, a triazaanthracene ring, a tetraazaanthracene ring, an azaphenanthracene ring, a diazophanthracene ring, a triazophanthracene ring or a tetraazophanthracene ring, and the group may have a substituent.

7. The composition according to any one of claims 1 to 4, wherein The oscillator strength of the compound T is greater than or equal to 0.0001.

8. The composition according to any one of claims 1 to 4, wherein The structural unit represented by formula (Y) is a structural unit represented by formula (Y-1), a structural unit represented by formula (Y-2), a structural unit represented by formula (Y-3), a structural unit represented by formula (Y-4), a structural unit represented by formula (Y-5), a structural unit represented by formula (Y-6), a structural unit represented by formula (Y-7), a structural unit represented by formula (Y-8), a structural unit represented by formula (Y-9) or a structural unit represented by formula (Y-10), In the formula, R Y1 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 may have a substituent. Y1 In the case of Y1 are optionally bonded to each other and together with the carbon atoms to which they are bonded form a ring, n Y1 Indicates 4; In the formula, R Y1 Means the same as above, X Y1 Indicates -C(R Y2 )2-、-C(R Y2 )=C(R Y2 )-or-C(R Y2 )2-C(R Y2 )2-, R Y2 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 may have a substituent. Y2 Optional same or different, R Y2 are optionally bonded to each other and together with the carbon atoms to which they are bonded form a ring, n Y2 represents 6, Where n Y1 、n Y2 , R Y1 and X Y1 Means the same as above, In the formula, R Y1 Means the same as above, R Y3 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 may have a substituent, In the formula, R Y1 Means the same as above, R Y4 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 may have a substituent.

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