Polymer compound, composition and light-emitting device

Abstract

To provide a polymer compound that is useful to produce a light-emitting element having an excellent luminance lifetime.SOLUTION: A polymer compound contains a constitutional unit represented by formula (1) [where n represents 0 or 1, R1, R2, R3, R4, R5, R6, R7 and R8 each represent a hydrogen atom, an alkyl group or the like, Ar1, Ar2, Ar3 and Ar4 each represent an arylene group or a divalent heterocyclic group, and XL1 represents a group represented by formula (X-1)].SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a polymer compound, a composition, and a light-emitting device. [Background technology]

[0002] As a hole transport material for use in a light-emitting element, for example, a polymer compound containing a structural unit derived from an arylamine represented by the following formula has been investigated (Patent Document 1).

[0003] [ka] [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Special Publication No. 2008-517135 Summary of the Invention [Problem to be solved by the invention]

[0005] However, the luminance life of the light-emitting device produced using the polymer compound is not necessarily sufficient. Therefore, a main object of the present invention is to provide a polymer compound that is useful for producing a light-emitting device having excellent luminance life. [Means for solving the problem]

[0006] The present invention provides the following [1] to

[13] . [1] A polymer compound comprising a constitutional unit represented by formula (1). [ka] [In the formula, n represents 0 or 1. R 1 , R 2 , R3 , R 4 , R 5 , R 6 , R 7 and R 8 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, or a halogen atom, and these groups may have a substituent. Ar 1 , Ar 2 , Ar 3 and Ar 4 each independently represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. Ar 1 and Ar 2 may be bonded to each other to form a ring together with the nitrogen atom to which they are bonded. 3 and Ar 4 may be bonded to each other to form a ring together with the nitrogen atom to which they are bonded. R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 6 and R 7 , R 6 and R 8 , R 1 and R 7 , R 1 and R 8 , and R 7 and R 8 may be bonded to each other to form a ring together with the carbon atom to which they are bonded. XL 1 represents a group represented by formula (X-1). XL 2 represents a hydrogen atom or a group represented by formula (X-1). [ka] [In the formula, * indicates the bond position. n1X represents an integer between 0 and 5 inclusive. L 1X represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, -NR 1X R represents a group represented by the formula (I)-, an oxygen atom, or a sulfur atom, and these groups may have a substituent. 1X L′ 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. 1X When multiple are present, they may be the same or different. X 1 represents a crosslinking group represented by formula (XL-1). [ka] [In the formula, *1 represents a bonding position.] [2] The above n 1X is 0. [3] The polymer compound according to [1] or [2], further comprising a constitutional unit represented by formula (Y): [ka] [In the formula, 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 to each other, and these groups may have a substituent.] [4] The polymer compound according to [3], wherein the constitutional unit represented by formula (Y) is a constitutional unit represented by formula (Y-1) or formula (Y-2). [ka] [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 may be the same or different, and adjacent RY1 may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. [ka] [In the formula, R Y1 has the same meaning as above. X Y1 is -C(R Y2 )2-, -C(R Y2 )=C(R Y2 )-or-C(R Y2 )2-C(R Y2 )2- represents a group represented by 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 may be the same or different, R Y2 may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. [5] The polymer compound according to any one of [1] to [4], further comprising a structural unit having a group in which one or more hydrogen atoms have been removed from the metal complex represented by formula (2). [ka] [In the formula, M represents a rhodium atom, a palladium atom, an iridium atom, or a platinum atom. n 1 represents an integer of 1 or more, and n 2 represents an integer of 0 or more. However, when M is a rhodium atom or an iridium atom, n 1 +n 2 is 3, and when M is a palladium atom or a platinum atom, n 1 +n 2 is 2. E 1 and E 2 Each independently represents a carbon atom or a nitrogen atom. 1 and E 2 At least one of E is a carbon atom.1 and E 2 When multiple are present, they may be the same or different. Ring L 1 represents an aromatic heterocycle, and this aromatic heterocycle may have a substituent. When a plurality of such substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded. Ring L 1 When multiple are present, they may be the same or different. Ring L 2 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings may have a substituent. When a plurality of such substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded. Ring L 2 When multiple are present, they may be the same or different. Ring L 1 and the ring L 2 may be bonded to each other to form a ring together with the atom to which they are bonded. A 1 -G 1 -A 2 represents an anionic bidentate ligand. 1 and A 2 Each of G independently represents a carbon atom, an oxygen atom, or a nitrogen atom, and these atoms may be atoms constituting a ring. 1 is a single bond or A 1 and A 2 A represents an atomic group that, together with 1 -G 1 -A 2 When multiple are present, they may be the same or different. [6] The polymer compound according to [5], wherein the structural unit having a group obtained by removing one or more hydrogen atoms from the metal complex represented by formula (2) is a structural unit represented by formula (1-1B), formula (1-2B), formula (1-3B), or formula (1-4B). [ka] [In the formula, M1B represents a group in which one hydrogen atom has been removed from the metal complex represented by the above formula (2). L C is an oxygen atom, a sulfur atom, -N(R A )-, -C(R B )2-, -C(R B )=C(R B R represents -, -C≡C-, an arylene group or a divalent heterocyclic group, and these groups may have a substituent. A 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. B 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. B may be the same or different and may be bonded to each other to form a ring together with the carbon atom to which they are bonded. C When multiple are present, they may be the same or different. n c1 represents an integer greater than or equal to 0.] [ka] [In the formula, M 1B has the same meaning as above. L d and L e are each independently an oxygen atom, a sulfur atom, or -N(R A )-, -C(R B )2-, -C(R B )=C(R B R represents -, -C≡C-, an arylene group or a divalent heterocyclic group, and these groups may have a substituent. A and R B has the same meaning as above. d and L e When multiple are present, they may be the same or different. n d1 and n e1Each independently represents an integer of 0 or more. d1 may be the same or different. Ar 1M represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent.] [ka] [In the formula, L d and n d1 has the same meaning as above. M 2B represents a group in which two hydrogen atoms have been removed from the metal complex represented by the formula (2). [ka] [In the formula, L d and n d1 has the same meaning as above. M 3B represents a group in which three hydrogen atoms have been removed from the metal complex represented by the formula (2). [7] The polymer compound according to [5] or [6], wherein the metal complex represented by formula (2) is a metal complex represented by formula (1-A): [ka] [In the formula, M, n 1 , n 2 , E 1 and A 1 -G 1 -A 2 has the same meaning as above. Ring L 1A represents a pyridine ring, a diazabenzene ring, an azanaphthalene ring, a diazanaphthalene ring, a triazole ring or a diazole ring, and these rings may have a substituent. When a plurality of such substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded. Ring L 1A When multiple are present, they may be the same or different. E 21A , E 22A , E 23A and E 24A Each of E independently represents a nitrogen atom or a carbon atom. 21A , E 22A , E 23A and E 24A When multiple are present, they may be the same or different. 21A When is a nitrogen atom, R 21A does not exist. 22A When is a nitrogen atom, R 22A does not exist. 23A When is a nitrogen atom, R 23A does not exist. 24A When is a nitrogen atom, R 24A does not exist. R 21A , R 22A , R 23A and R 24A R 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, or a halogen atom, and these groups may have a substituent. 21A , R 22A , R 23A and R 24A When multiple R are present, they may be the same or different. 21A and R 22A , R 22A and R 23A , R 23A and R 24A , and ring L 1A The substituents that may be present on R 21A may be bonded to each other to form a ring together with the atoms to which they are bonded. Ring L 2A represents a benzene ring, a pyridine ring, or a diazabenzene ring.] [8] The polymer compound according to [7], wherein the metal complex represented by formula (1-A) is a metal complex represented by formula (1-B1), formula (1-B2), formula (1-B3), formula (1-B4), or formula (1-B5). [ka] [In the formula, M, n 1 , n 2 , R 21A , R 22A , R 23A , R 24A and A 1 -G 1 -A 2 has the same meaning as above. n 11 and n 12 Each independently represents 1 or 2. However, when M is a rhodium atom or an iridium atom, n 11 +n 12 is 3, and when M is a palladium atom or a platinum atom, n 11 +n 12 is 2. R 11B , R 12B , R 13B , R 14B , R 15B , R 16B , R 17B and R 18B R 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, or a halogen atom, and these groups may have a substituent. 11B , R 12B , R 13B , R 14B , R 15B , R 16B , R 17B and R 18B When multiple are present, they may be the same or different. In formula (1-B1), R 11B and R 12B , R 12B and R 13B , R 13B and R 14B , and R 11B and R 21A may be bonded to each other to form a ring together with the atom to which each is bonded. 13B and R 14B, R 13B and R 15B , R 15B and R 16B , R 16B and R 17B , R 17B and R 18B , and R 18B and R 21A may be bonded to each other to form a ring together with the atom to which each is bonded. 11B and R 12B , R 12B and R 13B , R 13B and R 14B , R 11B and R 21A , R 13B and R 15B , R 15B and R 16B , R 16B and R 17B , R 17B and R 18B , and R 18B and R 21A may be bonded to each other to form a ring together with the atom to which they are bonded. 11B and R 18B , R 14B and R 15B , R 15B and R 16B , R 16B and R 17B , R 17B and R 18B , and R 11B and R 21A may be bonded to each other to form a ring together with the atom to which each is bonded. 11B and R 12B , R 12B and R 18B , R 15B and R 16B , R 16B and R 17B , R 17B and R 18B , and R 11B and R 21A may be bonded to each other to form a ring together with the atoms to which they are bonded. [9] The polymer compound according to any one of [1] to [8], further comprising a constitutional unit represented by formula (X): [ka] [In the formula, a X1 and a X2 each independently represents an integer of 0 or greater. Ar X1 and Ar X3 each independently represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. 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 to each other, and these groups may have a substituent. X2 and Ar X4 When multiple are present, they may be the same or different. R X1 , R X2 and R X3 R 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 When multiple are present, they may be the same or different.

[10] The polymer compound according to any one of [1] to [9], further comprising a structural unit having a crosslinking group selected from Group A of crosslinking groups. (Bridging group A group) [ka] [In the formula, R XL represents a methylene group, an oxygen atom, or a sulfur atom; n XL represents an integer from 0 to 5. XL When multiple are present, they may be the same or different. XLWhen there are a plurality of groups, they may be the same or different. *1 represents the bonding position. These bridging groups may have a substituent, and when there are a plurality of such substituents, they may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.]

[11] A polymer compound according to any one of [1] to

[10] , At least one selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, an antioxidant, and a solvent; A composition comprising:

[12] A light-emitting device having an anode, a cathode, and an organic layer provided between the anode and the cathode, the organic layer being a layer containing a crosslinked product of the polymer compound according to any one of [1] to

[10] .

[13] The light-emitting device according to

[12] , further comprising a light-emitting layer provided between the organic layer and the cathode. Effect of the Invention

[0007] According to the present invention, a polymer compound useful for producing a light-emitting device having excellent luminance life can be provided. According to the present invention, a composition containing the polymer compound can be provided. Furthermore, according to the present invention, a light-emitting device containing a crosslinked product of the polymer compound can be provided. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0008] Preferred embodiments of the present invention will now be described in detail.

[0009] <Explanation of common terms> Terms commonly used in this specification have the following meanings unless otherwise specified.

[0010] 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.

[0011] The hydrogen atom may be a deuterium atom or a protium atom.

[0012] In the formula representing a metal complex, the solid line representing a bond to a central metal means a covalent bond or a coordinate bond.

[0013] "Polymer compounds" are compounds that have a molecular weight distribution and have a number average molecular weight of 1 x 10 3 ~1×10 8 The polymer refers to a polymer in which

[0014] A "low molecular weight compound" is a compound that does not have a molecular weight distribution and has a molecular weight of 1×10 4 The following compound is meant:

[0015] The term "structural unit" refers to a unit that exists in a polymer compound, one or more of which are present.

[0016] The "alkyl group" may be either linear or branched. The number of carbon atoms in a linear alkyl group, not including the number of carbon atoms in the substituent, is usually 1 to 50, preferably 3 to 30, and more preferably 4 to 20. The number of carbon atoms in a branched alkyl group, not including the number of carbon atoms in the substituent, is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20. The alkyl group may have a substituent, and examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a 2-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, an isoamyl group, a 2-ethylbutyl group, a hexyl group, a heptyl group, an octyl group, a 2-ethylhexyl group, a 3-propylheptyl group, a decyl group, a 3,7-dimethyloctyl group, a 2-ethyloctyl group, a 2-hexyldecyl group, a dodecyl group, and groups in which the 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 (for example, a trifluoromethyl group, a pentafluoroethyl group, a perfluorobutyl group, a perfluorohexyl group, a perfluorooctyl group, a 3-phenylpropyl group, a 3-(4-methylphenyl)propyl group, a 3-(3,5-di-hexylphenyl)propyl group, and a 6-ethyloxyhexyl group). The number of carbon atoms in a "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. The cycloalkyl group may have a substituent, and examples thereof include a cyclohexyl group, a cyclohexylmethyl group, and a cyclohexylethyl group.

[0017] The term "aryl group" 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 the aryl group is usually 6 to 60, preferably 6 to 20, and more preferably 6 to 10, not including the number of carbon atoms of the substituent. The aryl group may have a substituent, and examples thereof include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthracenyl group, a 2-anthracenyl group, a 9-anthracenyl group, a 1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenyl group, a 2-fluorenyl group, a 3-fluorenyl group, a 4-fluorenyl group, a 2-phenylphenyl group, a 3-phenylphenyl group, a 4-phenylphenyl group, and groups in which a hydrogen atom in these groups is substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like.

[0018] The "alkoxy group" may be either linear or branched. The number of carbon atoms of a linear alkoxy group, not including the number of carbon atoms of the substituent, is usually 1 to 40, and preferably 4 to 10. The number of carbon atoms of a branched alkoxy group, not including the number of carbon atoms of the substituent, is usually 3 to 40, and preferably 4 to 10. The alkoxy group may have a substituent, and examples thereof include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group, an isobutyloxy group, a tert-butyloxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a 2-ethylhexyloxy group, a nonyloxy group, a decyloxy group, a 3,7-dimethyloctyloxy group, a lauryloxy group, and groups in which the 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. The number of carbon atoms in the "cycloalkoxy group" is usually 3 to 40, and preferably 4 to 10, not including the number of carbon atoms of the substituents. The cycloalkoxy group may have a substituent, and examples thereof include a cyclohexyloxy group.

[0019] The number of carbon atoms in the "aryloxy group" is usually 6 to 60, and preferably 6 to 48, not including the number of carbon atoms of substituents. The aryloxy group may have a substituent, and examples thereof include a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 1-anthracenyloxy group, a 9-anthracenyloxy group, a 1-pyrenyloxy group, and groups in which the hydrogen atoms in these groups are substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a fluorine atom, or the like.

[0020] The term "p-valent heterocyclic group" (p is an integer of 1 or more) refers to an atomic group remaining after removing p hydrogen atoms from among the hydrogen atoms directly bonded to carbon atoms or heteroatoms constituting the ring of a heterocyclic compound. Among p-valent heterocyclic groups, a "p-valent aromatic heterocyclic group" which is an atomic group remaining after removing p hydrogen atoms from among the hydrogen atoms directly bonded to carbon atoms or heteroatoms constituting the ring of an aromatic heterocyclic compound is preferred. The term "aromatic heterocyclic compound" refers to a compound in which the heterocycle itself exhibits aromaticity, such as oxadiazole, thiadiazole, thiazole, oxazole, thiophene, pyrrole, phosphole, furan, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole, or dibenzophosphole, and a compound in which an aromatic ring is condensed with a heterocycle, such as phenoxazine, phenothiazine, dibenzoborole, dibenzosilole, or benzopyran, even if the heterocycle itself does not exhibit aromaticity.

[0021] The monovalent heterocyclic group has usually 2 to 60 carbon atoms, and preferably 4 to 20 carbon atoms, not including the number of carbon atoms of the substituent. The monovalent heterocyclic group may have a substituent, and examples thereof include a thienyl group, a pyrrolyl group, a furyl group, a pyridyl group, a piperidinyl group, a quinolinyl group, an isoquinolinyl group, a pyrimidinyl group, a triazinyl group, and groups in which a hydrogen atom in these groups is substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or the like.

[0022] The term "halogen atom" refers to a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0023] 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. Examples of the substituted amino group include a dialkylamino group, a dicycloalkylamino group, and a diarylamino group. 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.

[0024] The "alkenyl group" may be either linear or branched. The number of carbon atoms in a linear alkenyl group, not including the number of carbon atoms in the substituent, is usually 2 to 30, and preferably 3 to 20. The number of carbon atoms in a branched alkenyl group, not including the number of carbon atoms in the substituent, is usually 3 to 30, and preferably 4 to 20. The number of carbon atoms in a "cycloalkenyl group" is usually 3 to 30, and preferably 4 to 20, not including the number of carbon atoms of substituents. The alkenyl group and cycloalkenyl group may have a substituent, and examples thereof include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 2-butenyl group, a 3-butenyl group, a 3-pentenyl group, a 4-pentenyl group, a 1-hexenyl group, a 5-hexenyl group, a 7-octenyl group, and groups in which these groups have a substituent.

[0025] The "alkynyl group" may be either linear or branched. The number of carbon atoms of the alkynyl group, not including the carbon atoms of the substituent, is usually 2 to 20, preferably 3 to 20. The number of carbon atoms of the branched alkynyl group, not including the carbon atoms of the substituent, is usually 4 to 30, preferably 4 to 20. The number of carbon atoms in the "cycloalkynyl group" is usually 4 to 30, and preferably 4 to 20, not including the carbon atoms of the substituents. The alkynyl group and cycloalkynyl group may have a substituent, and examples thereof include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 2-butynyl group, a 3-butynyl group, a 3-pentynyl group, a 4-pentynyl group, a 1-hexynyl group, a 5-hexynyl group, and groups in which these groups have a substituent.

[0026] The term "arylene group" 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, not including the number of carbon atoms of the substituent. The arylene group may have a substituent, and examples thereof include a phenylene group, a naphthalenediyl group, an anthracenediyl group, a phenanthrenediyl group, a dihydrophenanthrenediyl group, a naphthacenediyl group, a fluorenediyl group, a pyrenediyl group, a perylenediyl group, a chrysenediyl group, and groups in which these groups have a substituent, and are preferably groups represented by formulas (A-1) to (A-20). The arylene group includes groups in which a plurality of these groups are bonded. In addition, * indicates a bonding position.

[0027] [ka]

[0028] [ka]

[0029] [ka]

[0030] [ka] [Wherein, 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 may be the same or different, R a may be bonded to each other to form a ring together with the atoms to which they are bonded.

[0031] The divalent heterocyclic group has usually 2 to 60 carbon atoms, preferably 3 to 20 carbon atoms, and more preferably 4 to 15 carbon atoms, not including the number of carbon atoms of the substituent. The divalent heterocyclic group may have a substituent, and examples thereof include divalent groups obtained by removing two hydrogen atoms from pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilole, phenoxazine, phenothiazine, acridine, dihydroacridine, furan, thiophene, azole, diazole, and triazole that are directly bonded to carbon atoms or heteroatoms that constitute the ring, and preferably the groups represented by formulae (AA-1) to (AA-34). The divalent heterocyclic group includes groups in which a plurality of these groups are bonded. In addition, * indicates the bonding position.

[0032] [ka]

[0033] [ka]

[0034] [ka]

[0035] [ka]

[0036] [ka]

[0037] [ka]

[0038] [ka] [Wherein, R and R a has the same meaning as above.]

[0039] The "crosslinking group" is a group that can generate a new bond by being subjected to heating, ultraviolet light irradiation, near-ultraviolet light irradiation, visible light irradiation, infrared light irradiation, radical reaction, or the like, and is preferably a crosslinking group represented by formulae (XL-1) to (XL-19) in the crosslinking group A group.

[0040] [ka]

[0041] The "substituent" refers to a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an amino group, a substituted amino group, an alkenyl group, a cycloalkenyl group, an alkynyl group, or a cycloalkynyl group. The substituent may be a bridging group.

[0042] <Polymer compounds> The polymer compound of this embodiment contains a constitutional unit represented by formula (1).

[0043] [Structural unit represented by formula (1)] n represents 0 or 1, and is preferably 1.

[0044] R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, more preferably a hydrogen atom, an alkyl group, or a cycloalkyl group, and even more preferably a hydrogen atom, since this results in a longer luminance life for the light-emitting element. These groups may have a substituent.

[0045] R 7 and R 8R is preferably an alkyl group, a cycloalkyl group, or an aryl group, more preferably an alkyl group or an aryl group, and further preferably an alkyl group, since the luminance life of the light-emitting element is longer. R may have a substituent. 7 and R 8 It is preferred that does not contain a bridging group.

[0046] Ar 2 and Ar 3 is preferably an arylene group or a divalent heterocyclic group, more preferably an arylene group, since the luminance life of the light-emitting device is longer. However, Ar 2 and Ar 3 does not contain a bridging group.

[0047] Ar 2 and Ar 3 The arylene group represented by the formula (I) is preferably a phenylenediyl group which may have a substituent, and more preferably a phenylenediyl group which has no substituent, because it improves the solubility in organic solvents and the heat resistance of the polymer compound of this embodiment in a well-balanced manner.

[0048] Ar 1 and Ar 4 is preferably an arylene group or a divalent heterocyclic group, more preferably an arylene group, since the luminance life of the light-emitting device is longer. However, Ar 1 and Ar 4 does not contain a bridging group.

[0049] Ar 1 and Ar 4 The arylene group represented by the formula (I) is preferably a phenylenediyl group which may have a substituent, and more preferably a phenylenediyl group which has no substituent, because it improves the solubility in organic solvents and the heat resistance of the polymer compound of this embodiment in a well-balanced manner.

[0050] R 1 , R 2 , R 3, R 4 , R 5 , R 6 , R 7 and R 8 , and Ar 1 , Ar 2 , Ar 3 and Ar 4 The substituent which may be substituted is preferably an alkyl group, a cycloalkyl group or an aryl group.

[0051] "Ar 1 and Ar 2 may be bonded to each other to form a ring together with the nitrogen atom to which they are bonded. 3 and Ar 4 may be bonded to each other to form a ring together with the nitrogen atom to which they are bonded. 1 and Ar 2 (or Ar 3 and Ar 4 ) is a single bond, or -O-, -S-, -C(=O)-, -C(=O)-O-, -N(R 9 )-, -C(=O)-N(R 9 )- or -C(R 9 )2- represented by the group (R 9 R represents an alkyl group, a cycloalkyl group, or an aryl group, and these groups may have a substituent. 9 When a plurality of are present, they may be the same or different. It means that they may be bonded via a group () to form a ring.

[0052] "R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 6 and R 7 , R 6 and R 8 , R 1 and R 7 , R 1 and R 8 , and R 7 and R 8may be bonded to each other to form a ring together with the carbon atom to which each is bonded. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 This means that groups bonded to the same carbon atom may be bonded to each other to form a ring, or groups bonded to adjacent carbon atoms may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.

[0053] XL 2 is preferably formula (X-1).

[0054] [Group represented by formula (X-1)] n 1X represents an integer of 0 or more and 5 or less, preferably 0 or more and 3 or less, more preferably 0 or more and 1 or less, and even more preferably 0.

[0055] L 1X is preferably an alkylene group, a cycloalkylene group, an arylene group or a divalent heterocyclic group, more preferably an alkylene group, a cycloalkylene group or an arylene group, and further preferably an alkylene group or an arylene group, and these groups may have a substituent. The substituent is preferably an alkyl group, a cycloalkyl group or an aryl group.

[0056] The total amount of the structural units represented by formula (1) is preferably 10 to 90 mol %, more preferably 20 to 70 mol %, and even more preferably 30 to 50 mol %, based on the total amount of structural units contained in the polymer compound, since the polymer compound of this embodiment has excellent stability.

[0057] Examples of the constitutional unit represented by formula (1) include constitutional units represented by the following formulae (1-1) to (1-22). The constitutional unit represented by formula (1) is preferably a constitutional unit represented by formulae (1-1) to (1-20), more preferably a constitutional unit represented by formulae (1-1) to (1-8), and further preferably a constitutional unit represented by formulae (1-1) to (1-4). Here, * represents a bonding position.

[0058] [ka]

[0059] [ka]

[0060] [ka]

[0061] The polymer compound may contain only one type of constitutional unit represented by formula (1), or may contain two or more types.

[0062] The polymer compound of this embodiment preferably further contains a constitutional unit represented by formula (Y) since this provides a light-emitting device with a longer luminance life.

[0063] [ka] [In the formula, 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 to each other, and these groups may have a substituent.]

[0064] Ar Y1The arylene group represented by the formula (A-1), (A-6), (A-7), (A-9) to (A-11), (A-13) or (A-19) is preferably a group represented by the formula (A-1), (A-7), (A-9) or (A-19), and these groups may have a substituent.

[0065] Ar Y1 is preferably a group represented by formula (AA-4), (AA-10), (AA-13), (AA-15), (AA-18) or (AA-20), more preferably a group represented by formula (AA-4), (AA-10), (AA-18) or (AA-20), and these groups may have a substituent.

[0066] Ar Y1 In the divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, the preferred and more preferred ranges of the arylene group and the divalent heterocyclic group are respectively as defined above in Ar Y1 The preferred and more preferred ranges are the same as those of the arylene group and divalent heterocyclic group represented by the following formula:

[0067] Ar Y1 As the divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, Ar X2 and Ar X4 and at least one divalent heterocyclic group directly bonded to one or more arylene groups represented by the following formula:

[0068] Ar Y1 The substituent which the group represented by the following formula may have is preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups may further have a substituent.

[0069] Examples of the constitutional unit represented by formula (Y) include constitutional units represented by formulas (Y-1) to (Y-10). The constitutional unit represented by formula (Y) is preferably a constitutional unit represented by formulas (Y-1) to (Y-3) from the viewpoint of the luminance life of the light-emitting element, is preferably a constitutional unit represented by formulas (Y-4) to (Y-7) from the viewpoint of electron transportability, and is preferably a constitutional unit represented by formulas (Y-8) to (Y-10) from the viewpoint of hole transportability.

[0070] [ka] [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 may be the same or different, and adjacent R Y1 may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.

[0071] R Y1 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, and these groups may have a substituent.

[0072] The constitutional unit represented by formula (Y-1) is preferably a constitutional unit represented by formula (Y-1').

[0073] [ka] [In the formula, 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. Y11 may be the same or different.]

[0074] R Y11is preferably an alkyl group, a cycloalkyl group or an aryl group, more preferably an alkyl group or a cycloalkyl group, and these groups may have a substituent.

[0075] [ka] [In the formula, R Y1 has the same meaning as above. X Y1 is -C(R Y2 )2-, -C(R Y2 )=C(R Y2 )-or-C(R Y2 )2-C(R Y2 )2- represents a group represented by 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 may be the same or different, R Y2 may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.

[0076] R Y2 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, and these groups may have a substituent.

[0077] X Y1 In the above, -C(R Y2 )2-, where R Y2 The combination of R is preferably such that both are alkyl groups or cycloalkyl groups, both are aryl groups, both are monovalent heterocyclic groups, or one is an alkyl group or cycloalkyl group and the other is an aryl group or monovalent heterocyclic group, more preferably one is an alkyl group or cycloalkyl group and the other is an aryl group, and these groups may have a substituent. Y2may be bonded to each other to form a ring together with the atoms to which they are bonded, R Y2 When forms a ring, -C(R Y2 The group represented by 2- is preferably a group represented by formula (Y-A1) to formula (Y-A5), more preferably a group represented by formula (Y-A4). These groups may have a substituent. In addition, * represents a bonding position.

[0078] [ka]

[0079] X Y1 In the above, -C(R Y2 )=C(R Y2 Two R in the group represented by Y2 The combination of the above is preferably such that 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.

[0080] X Y1 In the above, -C(R Y2 )2-C(R Y2 )2-, where R Y2 is preferably an alkyl group or a cycloalkyl group which may have a substituent. Y2 may be bonded to each other to form a ring together with the atoms to which they are bonded, R Y2 When forms a ring, -C(R Y2 )2-C(R Y2 The group represented by (Y-)2- is preferably a group represented by formula (Y-B1) to formula (Y-B5), more preferably a group represented by formula (Y-B3), and these groups may have a substituent.

[0081] [ka] [In the formula, R Y2 has the same meaning as above. In addition, * indicates the bond position.]

[0082] The constitutional unit represented by formula (Y-2) is preferably a constitutional unit represented by formula (Y-2').

[0083] [ka] [In the formula, R Y1 and X Y1 has the same meaning as above.]

[0084] [ka] [In the formula, R Y1 and X Y1 has the same meaning as above.]

[0085] The constitutional unit represented by formula (Y-3) is preferably a constitutional unit represented by formula (Y-3').

[0086] [ka] [In the formula, R Y11 and X Y1 has the same meaning as above.]

[0087] [ka]

[0088] [ka] [In the formula, R Y1 has the same meaning 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.

[0089] RY3 is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups may have a substituent.

[0090] The structural unit represented by formula (Y-4) is preferably a structural unit represented by formula (Y-4'), and the structural unit represented by formula (Y-6) is preferably a structural unit represented by formula (Y-6').

[0091] [ka] [In the formula, R Y1 and R Y3 has the same meaning as above.]

[0092] [ka] [In the formula, R Y1 has the same meaning 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.

[0093] R Y4 is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups may have a substituent.

[0094] Examples of the structural unit represented by formula (Y) include structural units composed of arylene groups represented by formulas (Y-101) to (Y-146), structural units composed of divalent heterocyclic groups represented by formulas (Y-201) to (Y-209), and structural units composed of divalent groups in which at least one arylene group and at least one divalent heterocyclic group are directly bonded to each other represented by formulas (Y-301) to (Y-307).

[0095]

change

[0096]

change

[0097]

change

[0098]

change

[0099]

change

[0100]

change

[0101]

change

[0102]

change

[0103]

change

[0104]

change

[0105]

change

[0106] [ka]

[0107] [ka]

[0108] [ka]

[0109] [ka]

[0110] A structural unit represented by the formula (Y), Y1 A structural unit in which the substituent is an arylene group provides a light-emitting device with a longer luminance life, and therefore the structural unit preferably accounts for 0.5 to 80 mol %, and more preferably 30 to 60 mol %, of the total amount of structural units contained in the polymer compound.

[0111] A structural unit represented by the formula (Y), Y1 A structural unit in which is a divalent heterocyclic group or a divalent group in which at least one type of arylene group and at least one type of divalent heterocyclic group are directly bonded to each other has excellent charge transport properties in the light-emitting device, and therefore the amount of the structural unit is preferably 0.5 to 40 mol %, and more preferably 3 to 30 mol %, based on the total amount of the structural units contained in the polymer compound.

[0112] The polymer compound may contain only one type of constitutional unit represented by formula (Y), or may contain two or more types.

[0113] [Metal complex represented by formula (2)] The metal complex represented by formula (2) is usually a metal complex that exhibits phosphorescence at room temperature (25° C.), and is preferably a metal complex that exhibits luminescence from a triplet excited state at room temperature.

[0114] M is preferably an iridium atom or a platinum atom, and more preferably an iridium atom, since this provides a light-emitting device with better external quantum efficiency. When M is a rhodium atom or an iridium atom, n 1 is preferably 2 or 3, and more preferably 3. When M is a palladium atom or a platinum atom, n 1 is preferably 2. E 1 and E 2 Preferably, both are carbon atoms.

[0115] Ring L 1 The number of carbon atoms in the aromatic heterocycle is usually 2 to 60, preferably 3 to 30, and more preferably 4 to 15, not including the number of carbon atoms in the substituent. 1 is preferably a 6-membered aromatic heterocycle having one to four nitrogen atoms as constituent atoms, more preferably a 6-membered aromatic heterocycle having one to two nitrogen atoms as constituent atoms, and these rings may have a substituent. Ring L 1 Examples of the ring L include a pyridine ring, a diazabenzene ring, a triazine ring, an azanaphthalene ring, a dianaphthalene ring, and a triazanaphthalene ring. 1 is preferably a pyridine ring, a diazabenzene ring, an azanaphthalene ring or a dianaphthalene ring, more preferably a pyridine ring, a pyrimidine ring, a quinoline ring or an isoquinoline ring, and further preferably a pyridine ring or an isoquinoline ring. These rings may have a substituent.

[0116] Ring L 2The number of carbon atoms in the aromatic hydrocarbon ring in the ring L is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18, not including the number of carbon atoms in the substituent. 2 Examples of the aromatic hydrocarbon ring in include a benzene ring, a naphthalene ring, an indene ring, a fluorene ring, a spirobifluorene ring, a phenanthrene ring, a dihydrophenanthrene ring, and a fused ring in which one or more and five or less of these rings are fused. Since the external quantum efficiency of the light-emitting element of the present invention is more excellent, a benzene ring, a naphthalene ring, a fluorene ring, a spirobifluorene ring, a phenanthrene ring, or a dihydrophenanthrene ring is preferred, a benzene ring, a fluorene ring, a spirobifluorene ring, or a dihydrophenanthrene ring is more preferred, a benzene ring or a fluorene ring is even more preferred, and a benzene ring is particularly preferred. These rings may have a substituent.

[0117] Ring L 2 The number of carbon atoms in the aromatic heterocycle in the ring L is usually 2 to 60, preferably 3 to 30, and more preferably 4 to 15, not including the number of carbon atoms in the substituent. 2 Examples of the aromatic heterocycle in the formula (I) include a pyrrole ring, a diazole ring, a furan ring, a thiophene ring, a pyridine ring, a diazabenzene ring, and rings in which 1 to 5 aromatic rings are condensed to these rings. 2 The aromatic heterocycle in the above is preferably a pyridine ring, a diazabenzene ring, an azanaphthalene ring, a diazanaphthalene ring, an indole ring, a benzofuran ring, a benzothiophene ring, a carbazole ring, an azacarbazole ring, a diazacarbazole ring, a dibenzofuran ring, or a dibenzothiophene ring, since the external quantum efficiency of the light-emitting device is more excellent, more preferably a pyridine ring, a diazabenzene ring, a carbazole ring, a dibenzofuran ring, or a dibenzothiophene ring, and even more preferably a pyridine ring or a diazabenzene ring, and these rings may have a substituent. 2 When E is a 6-membered aromatic heterocycle, L is preferably a carbon atom.

[0118] Ring L 2is preferably a benzene ring, a fluorene ring, a dihydrophenanthrene ring, a pyridine ring, a diazabenzene ring, a carbazole ring, a dibenzofuran ring or a dibenzothiophene ring, since the external quantum efficiency of the light-emitting element is further improved, more preferably a benzene ring, a pyridine ring or a diazabenzene ring, and even more preferably a benzene ring, and these rings may have a substituent.

[0119] [Anionic bidentate ligand] A 1 -G 1 -A 2 Examples of the anionic bidentate ligand represented by the formula include the ligand represented by the formula: 1 -G 1 -A 2 The anionic bidentate ligand represented by the subscript n 1 The number of ligands is defined as different from that of the ligands.

[0120] [ka]

[0121] [ka] [In the formula, *M 1 represents the site of binding to R L1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, or a halogen atom, and these groups may have a substituent. L1 may be the same or different. R L2 represents an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a halogen atom, and these groups may have a substituent.

[0122] R L1is preferably a hydrogen atom, an alkyl group, a cycloalkyl group or a fluorine atom, more preferably a hydrogen atom or an alkyl group, and these groups may have a substituent. R L2 is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups may have a substituent.

[0123] The external quantum efficiency of the light-emitting device is superior, so 1 and ring L 2 At least one of these preferably has a group represented by formula (1-T).

[0124] [ka] [In the formula, R 1T represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an aryl group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom, and these groups may have a substituent.

[0125] "Ring L 1 and ring L 2 At least one of the rings L has a group represented by formula (1-T) 1 and ring L 2 In the metal complex represented by formula (2), the ring L is directly bonded to at least one of the atoms (preferably, a carbon atom or a nitrogen atom) constituting the ring. 1 and ring L 2 If there are multiple rings, there are multiple rings L 1 and ring L 2 At least one of the rings may have a group represented by formula (1-T). However, since the external quantum efficiency of the light-emitting device is improved, it is preferable to have a plurality of rings L 1 All of the rings L that exist multiple times 2 All or multiple rings L 1 and ring L 2It is preferable that all of the rings L 1 All or multiple rings L 2 It is more preferable that all of the above have a group represented by formula (1-T).

[0126] In the metal complex represented by formula (2), ring L 1 and ring L 2 Among these, at least one of them has the group represented by formula (1-T) in number of usually 1 to 5. Since the metal complex represented by formula (2) can be easily synthesized, the number of groups is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. In the metal complex represented by formula (2), when M is a rhodium atom or an iridium atom, the ring L 1 and ring L 2 The total number of groups represented by formula (1-T) contained in the compound (1) is usually 1 to 30, and since the external quantum efficiency of the light-emitting device is more excellent, it is preferably 1 to 18, more preferably 2 to 12, and even more preferably 3 to 6. In the metal complex represented by formula (2), when M is a palladium atom or a platinum atom, the ring L 1 and ring L 2 The total number of groups represented by formula (1-T) contained in the compound (1) is usually 1 to 20, and since the external quantum efficiency of the light-emitting device is more excellent, it is preferably 1 to 12, more preferably 1 to 8, and even more preferably 2 to 4.

[0127] Ring L 1 and ring L 2 The substituent other than the group represented by formula (1-T) that may be present is preferably a cyano group, an alkenyl group, or a cycloalkenyl group. These groups may further have a substituent.

[0128] Ring L 1 When there are a plurality of substituents which may be possessed by the group, they are preferably bonded to each other so as not to form a ring together with the atom to which they are bonded. Ring L 2When there are a plurality of substituents which may be possessed by the group, they are preferably bonded to each other so as not to form a ring together with the atom to which they are bonded. Ring L 1 and the ring L 2 It is preferable that the substituents which may be possessed by the group are not bonded to each other to form a ring together with the atoms to which they are bonded.

[0129] [Group represented by formula (1-T)] R 1T The aryl group represented by the formula (I) is preferably a phenyl group, a naphthyl group, a phenanthrenyl group, a dihydrophenanthrenyl group, a fluorenyl group, or a spirobifluorenyl group, more preferably a phenyl group, a fluorenyl group, or a spirobifluorenyl group, and still more preferably a phenyl group, and these groups may have a substituent. R 1T The monovalent heterocyclic group represented by the formula (I) is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a phenoxazinyl group, or a phenothiazinyl group, more preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothienyl group, or a carbazolyl group, and even more preferably a pyridyl group, a pyrimidinyl group, or a triazinyl group, and these groups may have a substituent. R 1T In the substituted amino group represented by the formula (I), the substituent of the amino group is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups may further have a substituent. Examples and preferred ranges of the aryl group and the monovalent heterocyclic group in the substituent of the amino group are as follows: 1T The examples and preferred ranges of the aryl group and monovalent heterocyclic group represented by the following formula are the same as those of the aryl group and monovalent heterocyclic group represented by the following formula:

[0130] R 1TThe substituent that may be contained in the alkyl group is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom, more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, still more preferably an alkyl group, a cycloalkyl group, or an aryl group, and particularly preferably an alkyl group. These groups may further have a substituent.

[0131] R 1T The substituent that the optionally substituted group may further have is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom, more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, and even more preferably an alkyl group or a cycloalkyl group, and these groups may further have a substituent.

[0132] R 1T is preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, more preferably an alkyl group, a cycloalkyl group or a group represented by formula (DA) to formula (DC), still more preferably an alkyl group or a group represented by formula (DA) or formula (DC), and particularly preferably a group represented by formula (DA). These groups may have a substituent.

[0133] [Group represented by formula (DA)] [ka] [In the formula, m DA1 , m DA2 and m DA3 each independently represents an integer of 0 or greater. G DArepresents a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent. Ar DA1 , Ar DA2 and Ar DA3 each independently represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. DA1 , Ar DA2 and Ar DA3 When multiple are present, they may be the same or different. T DA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. DA may be the same or different.]

[0134] [Group represented by formula (DB)] [ka] [In the formula, m DA1 , m DA2 , m DA3 , m DA4 , m DA5 , m DA6 and m DA7 each independently represents an integer of 0 or greater. G DA represents a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent. DA may be the same or different. Ar DA1 , Ar DA2 , Ar DA3 , Ar DA4 , Ar DA5 , Ar DA6 and Ar DA7 each independently represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. DA1 , Ar DA2 , Ar DA3 , Ar DA4 , Ar DA5 , Ar DA6 and ArDA7 When multiple are present, they may be the same or different. T DA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. DA may be the same or different.]

[0135] [Group represented by formula (DC)] [ka] [In the formula, m DA1 represents an integer greater than or equal to 0. Ar DA1 represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. Ar DA1 When multiple are present, they may be the same or different. T DA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.]

[0136] [Groups represented by formulae (DA) to (DC)] m DA1 ~m DA7 is usually an integer of 10 or less, preferably an integer of 5 or less, more preferably an integer of 2 or less, and even more preferably 0 or 1. DA2 ~m DA7 are preferably the same integer, and m DA1 ~m DA7 are more preferably the same integer.

[0137] G DA is preferably an aromatic hydrocarbon group or a heterocyclic group, and more preferably a group consisting of a benzene ring, a pyridine ring, a pyrimidine ring, a triazine ring, or a carbazole ring, by removing three hydrogen atoms directly bonded to carbon atoms or nitrogen atoms constituting the ring, and these groups may have a substituent. G DAThe substituent that may be contained in the alkyl group is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, more preferably an alkyl group, a cycloalkyl group, an alkoxy group, or a cycloalkoxy group, and further preferably an alkyl group or a cycloalkyl group, and these groups may have a substituent. G DA is preferably a group represented by formula (GDA-11) to formula (GDA-15), more preferably a group represented by formula (GDA-11) to formula (GDA-14), even more preferably a group represented by formula (GDA-11) or formula (GDA-14), and particularly a group represented by formula (GDA-11).

[0138] [ka] [In the formula, * denotes Ar in formula (DA). DA1 , Ar in formula (DB) DA1 , Ar in formula (DB) DA2 Or, Ar in formula (DB) DA3 Represents a bond with. ** indicates Ar in formula (DA). DA2 , Ar in formula (DB) DA2 , Ar in formula (DB) DA4 Or, Ar in formula (DB) DA6 Represents a bond with. *** represents Ar in formula (DA). DA3 , Ar in formula (DB) DA3 , Ar in formula (DB) DA5 Or, Ar in formula (DB) DA7 Represents a bond with. R DA R 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 further have a substituent. DA When there are multiple, they may be the same or different.

[0139] R DA is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group or a cycloalkoxy group, more preferably a hydrogen atom, an alkyl group or a cycloalkyl group, and these groups may have a substituent.

[0140] Ar DA1 ~Ar DA7 is preferably a phenylene group, a fluorenediyl group or a carbazolediyl group, more preferably a group represented by formula (ArDA-1) to formula (ArDA-6), still more preferably a group represented by formula (ArDA-1) to formula (ArDA-3), and particularly preferably a group represented by formula (ArDA-1), and these groups may have a substituent. In addition, * represents a bonding position.

[0141] [ka] [In the formula, R DA has the same meaning as above. R DB 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. DB When there are a plurality of groups, they may be the same or different and may be bonded to each other to form a ring together with the carbon atom to which they are bonded.

[0142] R DB is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, and even more preferably an aryl group, and these groups may have a substituent.

[0143] Ar DA1 ~Ar DA7 , R DA and R DB Examples of the substituents that may be substituted by G DA The examples and preferred ranges of the substituents which may be possessed by the group are the same as those of the substituents which may be possessed by the group.

[0144] T DA is preferably a group represented by formula (TDA-1) to formula (TDA-4), more preferably a group represented by formula (TDA-1) or formula (TDA-3), and even more preferably a group represented by formula (TDA-1). In addition, * represents a bonding position.

[0145] [ka] [In the formula, R DA and R DB has the same meaning as above.]

[0146] The group represented by formula (DA) is preferably a group represented by formula (D-A1) to formula (D-A5), more preferably a group represented by formula (D-A1), formula (D-A3) or formula (D-A5), and further preferably a group represented by formula (D-A1). Here, * represents a bonding position.

[0147] [ka] [In the formula, R p1 ~R p4 R each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or a halogen atom. p1 , R p2 and R p4 When there are multiple, they may be the same or different. np1 represents an integer of 0 to 5, np2 represents an integer of 0 to 3, np3 represents 0 or 1, and np4 represents an integer of 0 to 4. A plurality of np1 may be the same or different.]

[0148] The group represented by formula (DB) is preferably a group represented by formulae (D-B1) to (D-B3), more preferably a group represented by formula (D-B1), where * represents a bonding position.

[0149] [ka] [In the formula, R p1 ~R p3 R each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or a halogen atom. p1 and R p2 When there are multiple, they may be the same or different. np1 represents an integer of 0 to 5, np2 represents an integer of 0 to 3, and np3 represents 0 or 1. When there are a plurality of np1 and a plurality of np2, they may be the same or different.]

[0150] The group represented by formula (DC) is preferably a group represented by formulae (D-C1) to (D-C4), more preferably a group represented by formulae (D-C1) to (D-C3), still more preferably a group represented by formula (D-C1) or formula (D-C2), and particularly preferably a group represented by formula (D-C1). Here, * represents a bonding position.

[0151] [ka] [In the formula, R p4 ~R p6 R each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or a halogen atom. p4 ~R p6 When there are multiple, they may be the same or different. np4 represents an integer of 0 to 4, np5 represents an integer of 0 to 5, and np6 represents an integer of 0 to 5.

[0152] np1 is preferably 0 or 1. np2 is preferably 0 or 1, more preferably 0. np3 is preferably 0. np4 is preferably an integer of 0 to 2. np5 is preferably an integer of 1 to 3. np6 is preferably an integer of 0 to 2.

[0153] R p1 ~R p6 is preferably an alkyl group or a cycloalkyl group, more preferably a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group, a cyclohexyl group, or a tert-octyl group, and even more preferably a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group, or a tert-octyl group.

[0154] A structural unit having a group obtained by removing one or more hydrogen atoms from a metal complex represented by formula (2) (hereinafter, sometimes referred to as a "metal complex structural unit") has excellent external quantum efficiency of a light-emitting device and is easy to synthesize, and therefore is preferably a structural unit containing a group obtained by removing one to five hydrogen atoms from a metal complex represented by formula (2), more preferably a structural unit containing a group obtained by removing one to three hydrogen atoms from a metal complex represented by formula (2), still more preferably a structural unit represented by formulas (1-1B) to (1-4B), particularly preferably a structural unit represented by formulas (1-1B) to (1-3B), and particularly preferably a structural unit represented by formula (1-3B).

[0155] [Structural unit represented by formula (1-1B)] R A is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups may have a substituent.

[0156] R B is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, still more preferably a hydrogen atom or an alkyl group, and particularly preferably a hydrogen atom, and these groups may have a substituent.

[0157] L C is -C(R B)2-, an arylene group or a divalent heterocyclic group is preferred, and -C(R B )2- or an arylene group, more preferably an arylene group, and particularly preferably a group represented by formula (A-1) or (A-2), which may have a substituent.

[0158] L C Examples and preferred ranges of the arylene group and the divalent heterocyclic group represented by the following formula are respectively: Y1 The examples and preferred ranges of the arylene group and the divalent heterocyclic group are the same as those of the arylene group and the divalent heterocyclic group represented by the following formula:

[0159] R A , R B and L C Examples and preferred ranges of the substituents that may be substituted are as follows: Y1 The examples and preferred ranges of the substituents that may be possessed by the group represented by the following formula are the same as those.

[0160] n c1 is usually an integer of 0 to 10, preferably an integer of 0 to 5, more preferably an integer of 0 to 2, further preferably 0 or 1, and particularly preferably 0.

[0161] When formula (1) is a polymer compound containing a constitutional unit represented by formula (1-1B), the constitutional unit represented by formula (1-1B) is a terminal constitutional unit.

[0162] The term "terminal structural unit" refers to a structural unit at the end of a polymer compound, and the terminal structural unit is preferably a structural unit derived from a terminal capping agent in the production of the polymer compound.

[0163] M 1B is more preferably a group represented by formula (BM-1).

[0164] [ka] [In the formula, M 2 , E L , ring L 1 , ring L 2 and A 3 -G 2 -A 4 has the same meaning as above. Ring L 11 represents a 6-membered aromatic heterocycle, and these rings may have a substituent. When a plurality of the substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atom to which each is bonded. Ring L 12 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings may have a substituent. When a plurality of the substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atom to which each is bonded. However, ring L 11 and ring L 12 One of the groups has one bond. n 11 and n 12 Each independently represents an integer of 0 or more. 11 +n 12 is 1 or 2. 2 When is a rhodium atom or an iridium atom, n 11 +n 12 is 2, and M 2 When n is a palladium atom or a platinum atom, 11 +n 12 is 1.]

[0165] M 2 When is a rhodium atom or an iridium atom, n 11 It is preferred that the number is 2. M 2 When n is a palladium atom or a platinum atom, 11 It is preferred that the number is 1.

[0166] Ring L 11 When ring L has no bond, 11 The definition, examples and preferred ranges of the ring L 1 The definitions, examples and preferred ranges are the same as those of the above. Ring L 11 When has a bond, ring L 11 The definition, examples and preferred range of the ring moiety excluding the bond are the same as those of the ring L 1 The definitions, examples and preferred ranges are the same as those of the above.

[0167] Ring L 12 When ring L has no bond, 12 The definition, examples and preferred ranges of the ring L 2 The definitions, examples and preferred ranges are the same as those of the above. Ring L 12 When has a bond, ring L 12 The definition, examples and preferred range of the ring moiety excluding the bond are the same as those of the ring L 2 The definitions, examples and preferred ranges are the same as those of the above.

[0168] Ring L 11 and ring L 12 The definition, examples and preferred range of the substituents which may be possessed by ring L 1 and ring L 2 The definition, examples and preferred ranges of the substituents which may be possessed by are the same as those of the substituents which may be possessed by the group.

[0169] [Structural unit represented by formula (1-2B)] L d is -C(R B )2-, an arylene group or a divalent heterocyclic group is preferable, an arylene group or a divalent heterocyclic group is more preferable, an arylene group is further preferable, and a group represented by formula (A-1) or (A-2) is particularly preferable, and these groups may have a substituent. L e is -C(R B )2-, an arylene group or a divalent heterocyclic group is preferred, and -C(R B )2- or an arylene group, more preferably an arylene group, and particularly preferably a group represented by formula (A-1) or (A-2), which may have a substituent.

[0170] L dand L e Examples and preferred ranges of the arylene group and the divalent heterocyclic group represented by the following formula are respectively: Y1 The examples and preferred ranges of the arylene group and the divalent heterocyclic group are the same as those of the arylene group and the divalent heterocyclic group represented by the following formula:

[0171] n d1 and n e1 is usually an integer of 0 to 10, preferably an integer of 0 to 5, more preferably an integer of 0 to 2, further preferably 0 or 1, and particularly preferably 0.

[0172] Ar 1M is preferably a group in which three hydrogen atoms directly bonded to carbon atoms or hetero atoms constituting the ring have been removed from a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a dihydrophenanthrene ring, a pyridine ring, a diazabenzene ring, a triazine ring, a carbazole ring, a phenoxazine ring, or a phenothiazine ring, more preferably a group in which three hydrogen atoms directly bonded to carbon atoms constituting the ring have been removed from a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, or a dihydrophenanthrene ring, even more preferably a group in which three hydrogen atoms directly bonded to carbon atoms constituting the ring have been removed from a benzene ring or a fluorene ring, and particularly preferably a group in which three hydrogen atoms directly bonded to carbon atoms constituting the ring have been removed from a benzene ring, and these groups may have a substituent.

[0173] L d , L e and Ar 1M Examples of the substituents that may be possessed by Ar and the preferred range thereof are as described above. Y1 The examples and preferred ranges of the substituents that may be possessed by the group represented by the following formula are the same as those.

[0174] [Structural unit represented by formula (1-3B)] M 2B is more preferably a group represented by formula (BM-2) or (BM-3), and further preferably a group represented by formula (BM-2).

[0175] [ka] [In the formula, M 2 , E L , ring L 1 , ring L 2 , ring L 11 , ring L 12 and A 3 -G 2 -A 4 has the same meaning as above. 11 may be the same or different. 12 may be the same or different. n 13 and n 14 Each independently represents an integer of 0 or more. 13 +n 14 is 0 or 1. M 2 When is a rhodium atom or an iridium atom, n 13 +n 14 is 1, and M 2 When n is a palladium atom or a platinum atom, 13 +n 14 is 0.]

[0176] M 2 When is a rhodium atom or an iridium atom, n 13 It is preferred that the number is 1.

[0177] [ka] [In the formula, M 2 , E L , ring L 1 , ring L 2 , A 3 -G 2 -A 4 , n 11 and n 12 has the same meaning as above. Ring L 13represents a 6-membered aromatic heterocycle, and these rings may have a substituent. When a plurality of the substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atom to which each is bonded. Ring L 14 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings may have a substituent. When a plurality of the substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atom to which each is bonded. However, ring L 13 and ring L 14 one of the rings has two bonds, or the ring L 13 and ring L 14 Each of has one bond.

[0178] Ring L 13 When ring L has no bond, 13 The definition, examples and preferred ranges of ring L 1 The definitions, examples and preferred ranges are the same as those of the above.

[0179] Ring L 13 When has a bond, ring L 13 The definition, examples and preferred range of the ring moiety excluding the bond are as follows: Ring L 1 The definitions, examples and preferred ranges are the same as those of the above.

[0180] Ring L 14 When ring L has no bond, 14 The definition, examples and preferred ranges of ring L 2 The definitions, examples and preferred ranges are the same as those of the above.

[0181] Ring L 14 When has a bond, ring L 14 The definition, examples and preferred range of the ring moiety excluding the bond are as follows: Ring L 2 The definitions, examples and preferred ranges are the same as those of the above.

[0182] Ring L 13 and ring L 14 The definition, examples and preferred range of the substituents which may be possessed by ring L1 and ring L 2 The definition, examples and preferred ranges of the substituents which may be possessed by are the same as those of the substituents which may be possessed by the group.

[0183] Ring L 13 and ring L 14 Each of the groups preferably has one bond.

[0184] [Structural unit represented by formula (1-4B)] M 3B is preferably a group represented by formula (BM-4).

[0185] [ka] [In the formula, M 2 , E L , ring L 11 , ring L 12 , ring L 13 and ring L 14 has the same meaning as above. n 15 represents 0 or 1. 16 represents 1 or 3. However, M 2 When is a rhodium atom or an iridium atom, n 15 is 0 and n 16 is 3. M 2 When n is a palladium atom or a platinum atom, 15 is 1 and n 16 is 1.]

[0186] [Metal complex represented by formula (1-A)] The metal complex represented by formula (2) is preferably a metal complex represented by formula (1-A) since the metal complex represented by formula (2) has a higher external quantum efficiency of the light-emitting device.

[0187] Ring L 1A is preferably a pyridine ring, a pyrimidine ring, a quinoline ring or an isoquinoline ring, more preferably a pyridine ring or an isoquinoline ring, and further preferably a pyridine ring, and these rings may have a substituent. Ring L 1A The substituent that may be possessed by is preferably a group represented by formula (1-T). Ring L 1A Examples and preferred ranges of the substituents other than the group represented by formula (1-T) that may be possessed by the ring L 1 and ring L 2 The examples and preferred ranges of the substituents other than the group represented by formula (1-T) that may be possessed by the formula (1-T) are the same as those of the substituents. Ring L 1A When there are a plurality of substituents which may be possessed by the group, they are preferably bonded to each other so as not to form a ring together with the atom to which they are bonded.

[0188] Ring L 2A When E is a pyridine ring, 21A is a nitrogen atom in a pyridine ring, E 22A a pyridine ring in which E is a nitrogen atom, or 23A is preferably a pyridine ring in which E 22A is more preferably a pyridine ring in which the nitrogen atom is present. Ring L 2A When E is a diazabenzene ring, 21A and E 23A a pyrimidine ring in which E is a nitrogen atom, or 22A and E 24A is preferably a pyrimidine ring in which E 22A and E 24A is a nitrogen atom in the pyrimidine ring is more preferred.

[0189] E 21A ~E 24A is preferably a carbon atom. Ring L 2A is preferably a benzene ring.

[0190] The external quantum efficiency of the light-emitting device is superior, so 1A At least one of R has a group represented by formula (1-T) or R 21A ~R 24AIt is preferable that at least one of these is a group represented by formula (1-T).

[0191] Ring L 1A When at least one of the rings has a group represented by formula (1-T), the ring L 1A The group represented by formula (1-T) may be directly bonded to at least one of the atoms (preferably carbon atoms or nitrogen atoms) constituting the ring L. 1A At least one of the rings L 1A If there are multiple rings, there are multiple rings L 1A At least one of the rings may have a group represented by formula (1-T). However, since the external quantum efficiency of the light-emitting device is improved, it is preferable to have a plurality of rings L 1A It is preferable that at least two of the rings L 1A It is more preferable that all of the above have a group represented by formula (1-T).

[0192] R 21A ~R 24A When at least one of R is a group represented by formula (1-T), the external quantum efficiency of the light-emitting device is superior. 22A and R 23A It is preferable that at least one of R is a group represented by formula (1-T). 22A or R 23A is more preferably a group represented by formula (1-T), and R 22A is more preferably a group represented by formula (1-T).

[0193] The metal complex represented by formula (1-A) can be easily synthesized, so R 21A and R 24A It is preferable that at least one of R is a hydrogen atom. 21A or R 24A is more preferably a hydrogen atom, and R 21A and R 24A It is more preferable that is a hydrogen atom.

[0194] The total number of groups represented by formula (1-T) in the metal complex represented by formula (1-A) is the same as that of the ring L in the metal complex represented by formula (2). 1 and ring L 2 is equal to the total number of groups represented by formula (1-T) contained in

[0195] R 21A and R 22A , R 22A and R 23A , R 23A and R 24A , and ring L 1A The substituents that may be present on R 21A is preferably not bonded to form a ring together with the atom to which it is bonded.

[0196] The metal complex represented by formula (1-A) has a better external quantum efficiency of the light-emitting element, and is therefore preferably a metal complex represented by formulas (1-B1) to (1-B5), more preferably a metal complex represented by formulas (1-B1) to (1-B3), further preferably a metal complex represented by formula (1-B1) or formula (1-B2), and particularly preferably a metal complex represented by formula (1-B1).

[0197] [ka] [In the formula, M, n 1 , n 2 , R 21A , R 22A , R 23A , R 24A and A 1 -G 1 -A 2 has the same meaning as above. n 11 and n 21 Each independently represents an integer of 1 or more, provided that when M is a rhodium atom or an iridium atom, n 11 +n 21 is 3, and when M is a palladium atom or a platinum atom, n 11 +n 21 is 2. R 11B , R 12B , R 13B , R 14B , R 15B , R 16B , R 17B and R 18B R each independently represents a hydrogen atom or a group represented by the above formula (1-T). 11B , R 12B , R 13B , R 14B , R 15B , R 16B , R 17B and R 18B When multiple are present, they may be the same or different. In formula (1-B1) and formula (1-B3), R 11B and R 12B , R 12B and R 13B , R 13B and R 14B , and R 11B and R 21A may be bonded to each other to form a ring together with the atom to which each is bonded. 13B and R 14B , R 13B and R 15B , R 15B and R 16B , R 16B and R 17B , R 17B and R 18B , and R 18B and R 21A may be bonded to each other to form a ring together with the atom to which they are bonded. 11B and R 18B , R 14B and R 15B , R 15B and R 16B , R 16B and R 17B , R 17B and R 18B , and R 11B and R 21A may be bonded to each other to form a ring together with the atom to which each is bonded. 11B and R12B , R 12B and R 18B , R 15B and R 16B , R 16B and R 17B , R 17B and R 18B , and R 11B and R 21A may be bonded to each other to form a ring together with the atoms to which they are bonded.

[0198] In formula (1-B1), since the external quantum efficiency of the light-emitting device is superior, R 11B ~R 14B and R 21A ~R 24A In formula (1-B1), at least one of R 11B ~R 14B is a group represented by formula (1-T), R 12B and R 13B It is preferable that at least one of R is a group represented by formula (1-T). 12B or R 13B is more preferably a group represented by formula (1-T), and R 13B is more preferably a group represented by formula (1-T). In formula (1-B1), since the external quantum efficiency of the light-emitting device is further improved, R 12B , R 13B , R 22A and R 23A It is more preferable that at least one of R is a group represented by formula (1-T). 13B , R 22A and R 23A It is more preferable that at least one of R is a group represented by formula (1-T). 13B and R 22A It is more preferable that at least one of R is a group represented by formula (1-T), 13B or R 22A is particularly preferably a group represented by formula (1-T).

[0199] In formula (1-B2), since the external quantum efficiency of the light-emitting device is superior, R13B ~R 18B and R 21A ~R 24A At least one of R is preferably a group represented by formula (1-T). 12B , R 13B , R 22A and R 23A It is more preferable that at least one of R is a group represented by formula (1-T). 22A and R 23A It is more preferable that at least one of R is a group represented by formula (1-T), 22A or R 23A is particularly preferably a group represented by formula (1-T).

[0200] In formula (1-B3), since the external quantum efficiency of the light-emitting device is superior, R 11B ~R 18B and R 21A ~R 24A At least one of R is preferably a group represented by formula (1-T). 12B , R 13B , R 22A and R 23A It is more preferable that at least one of R is a group represented by formula (1-T). 13B and R 22A It is more preferable that at least one of R is a group represented by formula (1-T), 13B or R 22A is particularly preferably a group represented by formula (1-T). In formula (1-B4), since the external quantum efficiency of the light-emitting device is superior, R 11B , R 14B ~R 18B and R 21A ~R 24A It is preferable that at least one of R is a group represented by formula (1-T). 22A and R 23A It is more preferable that at least one of them is a group represented by formula (1-T). In formula (1-B5), since the external quantum efficiency of the light-emitting device is superior, R 11B , R 12B , R 15B ~R 18B and R21A ~R 24A It is preferable that at least one of R is a group represented by formula (1-T). 22A and R 23A At least one of these is preferably a group represented by formula (1-T).

[0201] In formula (1-B1) and formula (1-B3), R 11B and R 12B , R 12B and R 13B , R 13B and R 14B , and R 11B and R 21A In formula (1-B2) and formula (1-B3), R 13B and R 14B , R 13B and R 15B , R 15B and R 16B , R 16B and R 17B , R 17B and R 18B , and R 18B and R 21A In formula (1-B4), R 11B and R 18B , R 14B and R 15B , R 15B and R 16B , R 16B and R 17B , R 17B and R 18B , and R 11B and R 21A In formula (1-B5), R 11B and R 12B , R 12B and R 18B , R 15B and R 16B , R 16B and R 17B , R 17B and R 18B , and R 11B and R21A is preferably not bonded to form a ring together with the atom to which it is bonded.

[0202] The total number of groups represented by formula (1-T) contained in the metal complexes represented by formulas (1-B1) to (1-B5) is the same as or smaller than the number of rings L in the metal complex represented by formula (2). 1 and ring L 2 is equal to the total number of groups represented by formula (1-T) contained in

[0203] Examples of the metal complex represented by formula (2) include metal complexes represented by the following formula:

[0204] [ka]

[0205] [ka]

[0206] [ka]

[0207] [ka]

[0208] [ka]

[0209] [ka]

[0210] Examples of structural units having a group in which one or more hydrogen atoms have been removed from a metal complex represented by formula (2) include metal complexes represented by formulae (1G-1) to (1G-13), (2G-1) to (2G-16), (3G-1) to (3G-23), (4G-1) to (4G-6) and (5G-1). In addition, * indicates a bonding position.

[0211] [ka]

[0212] [ka]

[0213] [ka]

[0214] [ka]

[0215] [ka]

[0216] [ka]

[0217] [ka] [In the formula, R D 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. D may be the same or different. De represents a group represented by formula (DA), formula (DB) or formula (DC).

[0218] The metal complex constituent unit is preferably 0.01 to 50 mol %, more preferably 0.1 to 30 mol %, further preferably 0.5 to 10 mol %, and particularly preferably 1 to 5 mol % relative to the total amount of the constituent units contained in the polymer compound, since the external quantum efficiency of the light-emitting device is excellent. Only one type of metal complex constituent unit or two or more types of metal complex constituent units may be contained in the polymer compound.

[0219] The metal complex represented by formula (2) is available from Aldrich, Luminescence Technology Corp., American Dye Source, etc. In addition, it can be synthesized according to the methods described in, for example, "Journal of the American Chemical Society, Vol. 107, 1431-1432 (1985)", "Journal of the American Chemical Society, Vol. 106, 6647-6653 (1984)", JP-T 2004-530254, JP-A 2008-179617, JP-A 2011-105701, JP-T 2007-504272, and WO 2006 / 121811.

[0220] [Other building blocks] The polymer compound of this embodiment preferably further contains a constitutional unit represented by formula (X) because it has excellent hole transport properties.

[0221] a X1 is preferably 2 or less, and more preferably 1, since the luminance life of the light-emitting element is superior.

[0222] a X2 is preferably 2 or less, and more preferably 0, since the luminance life of the light-emitting element is superior.

[0223] R X1 , R X2 and R X3is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups may have a substituent.

[0224] Ar X1 and Ar X3 The arylene group represented by the formula (A-1) or (A-9) is preferably a group represented by the formula (A-1), and more preferably a group represented by the formula (A-1). These groups may have a substituent.

[0225] Ar X1 and Ar X3 The divalent heterocyclic group represented by the formula (AA-1), (AA-2) or (AA-7) to (AA-26) is preferably a group represented by the formula (AA-1), (AA-2) or (AA-7) to (AA-26), and these groups may have a substituent.

[0226] Ar X1 and Ar X3 is preferably an arylene group which may have a substituent.

[0227] Ar X2 and Ar X4 The arylene group represented by the formula (A-1), (A-6), (A-7), (A-9) to (A-11) or (A-19) is preferably a group represented by the formula (A-1), and these groups may have a substituent.

[0228] Ar X2 and Ar X4 A preferred range of the divalent heterocyclic group represented by Ar X1 and Ar X3 The preferred range is the same as that of the divalent heterocyclic group represented by the following formula:

[0229] Ar X2 and Ar X4 In the divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, more preferred and even more preferred ranges of the arylene group and the divalent heterocyclic group are, respectively, X1 and Ar X3The more preferred and further preferred ranges are the same as those of the arylene group and divalent heterocyclic group represented by the following formula:

[0230] Ar X2 and Ar X4 Examples of the divalent group in which at least one arylene group represented by the formula (I) is directly bonded to at least one divalent heterocyclic group include groups represented by the formula (I) below. These may have a substituent. In addition, * represents the bonding position.

[0231] [ka] [In the formula, 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.

[0232] R XX is preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups may have a substituent.

[0233] Ar X2 and Ar X4 is preferably an arylene group which may have a substituent.

[0234] Ar X1 , Ar X2 , Ar X3 and Ar X4 , and R X1 , R X2 and R X3 The substituent which the group represented by the formula (I) may have is preferably an alkyl group, a cycloalkyl group or an aryl group. These groups may further have a substituent.

[0235] The constitutional unit represented by formula (X) is preferably a constitutional unit represented by formulas (X-1) to (X-7), more preferably a constitutional unit represented by formulas (X-3) to (X-7), and even more preferably a constitutional unit represented by formulas (X-3) to (X-6).

[0236] [ka]

[0237] [ka]

[0238] [ka]

[0239] [ka] [In the formula, 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 may be the same or different. X5 may be the same or different, and adjacent R X5 may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.

[0240] The structural unit represented by formula (X) has excellent hole transport properties, and therefore the amount of the structural unit 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 compound.

[0241] Examples of the constitutional unit represented by formula (X) include constitutional units represented by formulas (X1-1) to (X1-23). ​​The constitutional unit represented by formula (X) is preferably a constitutional unit represented by formulas (X1-6) to (X1-14).

[0242] [ka]

[0243] [ka]

[0244] [ka]

[0245] [ka]

[0246] [ka]

[0247] [ka]

[0248] [ka]

[0249] The polymer compound of this embodiment may contain only one type of constitutional unit represented by formula (X), or may contain two or more types.

[0250] The polymer compound of the present embodiment preferably further contains a structural unit having a crosslinking group selected from Group A of crosslinking groups, since the crosslinking property of the polymer compound is excellent.

[0251] The crosslinking group selected from the crosslinking group Group A is preferably a crosslinking group represented by formula (XL-1), (XL-3), (XL-5), (XL-7), (XL-16) or (XL-17) since the crosslinking property of the polymer compound of this embodiment is excellent, and more preferably a crosslinking group represented by formula (XL-1) or (XL-17). The constitutional unit having at least one crosslinking group selected from the crosslinking group Group A is preferably a constitutional unit represented by formula (Z) or a constitutional unit represented by formula (Z') described later, but may also be a constitutional unit represented by the following formula:

[0252] [ka]

[0253] The structural unit having at least one crosslinking group selected from the crosslinking group group A is preferably a structural unit represented by formula (Z) or a structural unit represented by formula (Z'), provided that the structural unit represented by formula (Z') is different from the structural unit represented by formula (1).

[0254] [Structural unit represented by formula (Z)] [ka] In the formula, nA represents an integer of 0 to 5, and nZ represents 1 or 2. When a plurality of nAs are present, they may be the same or different. Z1 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent. 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. L A When a plurality of X's are present, they may be the same or different. X represents a crosslinking group selected from the crosslinking group Group A. When a plurality of X's are present, they may be the same or different.

[0255] nA is preferably 0 or 1, and more preferably 0, since the luminance life of the light-emitting element is superior.

[0256] nZ is preferably 2 since the luminance life of the light emitting device is better.

[0257] Ar Z1 is preferably an aromatic hydrocarbon group which may have a substituent, since this provides a light-emitting device with a superior luminance life.

[0258] Ar Z1 The number of carbon atoms of the aromatic hydrocarbon group represented by the following formula (I) is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18, not including the number of carbon atoms of the substituent. Ar Z1 The arylene group portion excluding the n substituents of the aromatic hydrocarbon group represented by the formula (A-1) to (A-20) is preferably a group represented by the formula (A-1), (A-2), (A-6) to (A-10), (A-19) or (A-20), and more preferably a group represented by the formula (A-1), (A-2), (A-7), (A-9) or (A-19). These groups may have a substituent.

[0259] Ar Z1 The number of carbon atoms of the heterocyclic group represented by the following formula (1) is usually 2 to 60, preferably 3 to 30, and more preferably 4 to 18, not including the number of carbon atoms of the substituent. Ar Z1 The divalent heterocyclic group moiety excluding the nZ substituents of the heterocyclic group represented by the following formulae is preferably a group represented by the formulae (AA-1) to (AA-34).

[0260] Ar Z1 The aromatic hydrocarbon group and the heterocyclic group represented by the formula (I) may have a substituent, and examples of the substituent include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a halogen atom, a monovalent heterocyclic group, and a cyano group.

[0261] L A The alkylene group represented by the formula (I) generally has 1 to 20 carbon atoms, preferably 1 to 15 carbon atoms, and more preferably 1 to 10 carbon atoms, not including the carbon atom number of the substituent. A The cycloalkylene group represented by the following formula (1) typically has 3 to 20 carbon atoms, not including the number of carbon atoms of the substituent. The alkylene group and cycloalkylene group may have a substituent, and examples thereof include a methylene group, an ethylene group, a propylene group, a butylene group, a hexylene group, a cyclohexylene group, and an octylene group.

[0262] L A The alkylene group and cycloalkylene group represented by the following formula (1) may have a substituent. Examples of the substituent that the alkylene group and cycloalkylene group may have include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a halogen atom, and a cyano group.

[0263] L A The arylene group represented by the formula (I) may have a substituent. Examples of the arylene group include o-phenylene, m-phenylene, and p-phenylene. Examples of the substituent that the arylene group may have include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a halogen atom, a cyano group, and a crosslinking group selected from the crosslinking group A group.

[0264] L A is preferably a phenylene group or an alkylene group, since this facilitates the production of the polymer compound of this embodiment, and these groups may have a substituent.

[0265] The crosslinking group represented by X is preferably a crosslinking group represented by formula (XL-1), formula (XL-3), formula (XL-5), formula (XL-7), formula (XL-16) or formula (XL-17), since the crosslinking property of the polymer compound of this embodiment is excellent, and more preferably a crosslinking group represented by formula (XL-1) or formula (XL-17).

[0266] The structural unit represented by formula (Z) provides excellent stability and crosslinkability to the polymer compound of this embodiment, and therefore is preferably 0.5 to 50 mol %, more preferably 3 to 30 mol %, and even more preferably 3 to 20 mol %, relative to the total amount of structural units contained in the polymer compound.

[0267] The polymer compound may contain only one type of constitutional unit represented by formula (Z), or may contain two or more types.

[0268] [Structural unit represented by formula (Z')] [ka] In the formula, mA represents an integer of 0 to 5, m represents an integer of 1 to 4, and c represents an integer of 0 or 1. When a plurality of mA are present, they may be the same or different. Z3 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. Z2 and Ar Z4 each independently represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. Z2 , Ar Z3 and Ar Z4 may be bonded to a group other than the group bonded to the nitrogen atom to which the group is bonded, either directly or via an oxygen atom or a sulfur atom, to form a ring. 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. K AWhen a plurality of X' are present, they may be the same or different. 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 have a substituent. When a plurality of X' are present, they may be the same or different. However, at least one X' is a crosslinking group selected from the crosslinking group group A.]

[0269] mA is preferably 0 or 1, and more preferably 0, since the luminance life of the light-emitting element is superior.

[0270] m is preferably 2 since the luminance life of the light-emitting element is better.

[0271] c is preferably 0, since the polymer compound of this embodiment can be easily produced and the luminance life of the light-emitting device is superior.

[0272] Ar Z3 is preferably an aromatic hydrocarbon group which may have a substituent, since this provides a light-emitting device with a superior luminance life.

[0273] Ar Z3 The definition and examples of the arylene group moiety excluding the m substituents of the aromatic hydrocarbon group represented by the formula (X) are X2 The definition and examples of the arylene group are the same as those of the arylene group represented by the following formula:

[0274] Ar Z3 The definition and examples of the divalent heterocyclic group moiety excluding the m-number of substituents of the heterocyclic group represented by the formula (X) are as follows: X2 The definition and examples are the same as those of the divalent heterocyclic group moiety represented by the following formula:

[0275] Ar Z3 The definition and examples of the divalent group excluding the m-number of substituents of the group in which at least one aromatic hydrocarbon ring and at least one heterocycle are directly bonded, are the same as those of Ar X2The definition and examples are the same as those of the divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded to each other, and which is represented by the following formula:

[0276] Ar Z2 and Ar Z4 is preferably an arylene group which may have a substituent, since this provides a light-emitting element with a longer luminance life.

[0277] Ar Z2 and Ar Z4 The definition and examples of the arylene group represented by the formula (X) are as follows: X1 and Ar X3 The definition and examples of the arylene group are the same as those of the arylene group represented by the following formula:

[0278] Ar Z2 and Ar Z4 The definition and examples of the divalent heterocyclic group represented by the formula (X) are as follows: X1 and Ar X3 The definition and examples are the same as those of the divalent heterocyclic group represented by the following formula:

[0279] Ar Z2 , Ar Z3 and Ar Z4 The group represented by the formula (I) may have a substituent. Examples of the substituent include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a halogen atom, a monovalent heterocyclic group, and a cyano group.

[0280] K A The definitions and examples of the alkylene group, cycloalkylene group, arylene group, and divalent heterocyclic group represented by the following formula are respectively: A The definitions and examples are the same as those of the alkylene group, cycloalkylene group, arylene group, and divalent heterocyclic group represented by the following formula:

[0281] K A is preferably a phenylene group or a methylene group, since this facilitates the production of the polymer compound of this embodiment.

[0282] The crosslinking group represented by X' is preferably a crosslinking group represented by formula (XL-1), (XL-3), (XL-5), (XL-7), (XL-16) or (XL-17), since the crosslinking property of the polymer compound of this embodiment is excellent, and more preferably a crosslinking group represented by formula (XL-1) or (XL-17).

[0283] The structural unit represented by formula (Z') is preferably 0.5 to 50 mol %, more preferably 3 to 30 mol %, and even more preferably 3 to 20 mol %, relative to the total amount of structural units contained in the polymer compound, since the polymer compound of this embodiment has excellent stability and excellent crosslinkability.

[0284] The polymer compound may contain only one type of constitutional unit represented by formula (Z'), or may contain two or more types.

[0285] Examples of the constitutional unit represented by formula (Z) include constitutional units represented by formula (2-1) to formula (2-33), and examples of the constitutional unit represented by formula (Z') include constitutional units represented by formula (2'-1) to formula (2'-9). Among these, the constitutional unit represented by formula (Z) is preferably a constitutional unit represented by formula (2-1) to formula (2-30), more preferably a constitutional unit 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), and even more preferably a constitutional unit represented by formula (2-1) to formula (2-9) or formula (2-30). In addition, the constitutional unit represented by formula (Z) is also preferably a constitutional unit represented by formula (2-31) to formula (2-33), since the crosslinkability of the polymer compound of this embodiment is excellent.

[0286] [ka]

[0287] [ka]

[0288] [ka]

[0289] [ka]

[0290] Examples of the polymer compound of this embodiment include polymer compounds P-1 to P-12 shown in Table 1. Here, "other" refers to structural units other than those represented by formula (1), formula (Z), formula (Z'), formula (X) and formula (Y).

[0291] [Table 1] [In the table, p, q, r, s, t, u, and v represent the molar ratios of each structural unit. p+q+r+s+t+u=100, and 70≦p+q+r+s+t≦100.]

[0292] In the polymer compounds P-1 to P-16, examples and preferred ranges of the structural units represented by formula (1), formula (Y), formula (2), formula (X), formula (Z) and formula (Z') are as described above.

[0293] The terminal group of the polymer compound of this embodiment is preferably a stable group, since if the polymerization active group remains as it is, the light-emitting properties and luminance life may be deteriorated when the polymer compound is used for producing a light-emitting device. Examples of the terminal group include a group that is conjugated with the main chain, and a group that is bonded to an aryl group or a monovalent heterocyclic group via a carbon-carbon bond.

[0294] The polymer compound of the present embodiment may be any one of a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, or other forms, but is preferably a copolymer obtained by copolymerizing a plurality of types of raw material monomers.

[0295] <Method of producing polymer compound> Next, a method for producing the polymer compound of this embodiment will be described.

[0296] The polymer compound of this embodiment can be produced, for example, by condensation polymerization of only the compound represented by formula (M-1), or by condensation polymerization of the compound represented by formula (M-1) and another compound (for example, the compound represented by formula (M-2)). In this specification, the compounds used in the production of the polymer compound of this embodiment may be collectively referred to as "raw material monomers".

[0297] [ka]

[0298] [ka] [In the formula, n, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , Ar 1 , Ar 2 , Ar 3 , Ar 4 , XL 1 , XL 2 and Ar Y1 has the same meaning as above. Z C1 , Z C2 , Z C3 and Z C4 each independently represents a group selected from the group consisting of Substituent Group A and Substituent Group B.]

[0299] For example, Z C1 and Z C2 is a group selected from the substituent group A, Z C3 and Z C4 is selected from the substituent group B.

[0300] For example, Z C1 and Z C2 is a group selected from the substituent group B, Z C3 and Z C4 is a group selected from the substituent group A.

[0301] [Substituent group A] Chlorine atom, bromine atom, iodine atom, -OS(=O)2R C1 (In the formula, R C1 represents an alkyl group, a cycloalkyl group or an aryl group, and these groups may have a substituent.

[0302] [Substituent group B] -B(OR C2 )2(wherein, R C2 represents a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, and these groups may have a substituent. C2 may be the same or different and may be linked to each other to form a ring structure together with the oxygen atom to which they are bonded; A group represented by -BF3Q' (wherein Q' represents Li, Na, K, Rb or Cs); A group represented by -MgY' (wherein Y' represents a chlorine atom, a bromine atom, or an iodine atom); -ZnY″ (wherein Y″ represents a chlorine atom, a bromine atom, or an iodine atom); and -Sn(R C3 )3(wherein, R C3 represents a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, and these groups may have a substituent. C3 may be the same or different and may be linked to each other to form a ring structure together with the tin atom to which they are bonded.

[0303] -B(OR C2 Examples of the group represented by formula 2 include groups represented by the following formulas:

[0304] [ka]

[0305] A compound having a group selected from the substituent group A and a compound having a group selected from the substituent group B are condensation polymerized by a known coupling reaction to bond carbon atoms bonded to a group selected from the substituent group A and a group selected from the substituent group B. Therefore, by subjecting a compound having two groups selected from the substituent group A and a compound having two groups selected from the substituent group B to a known coupling reaction, a condensation polymer of these compounds can be obtained by condensation polymerization.

[0306] The condensation polymerization is usually carried out in the presence of a catalyst, a base and a solvent, and may be carried out in the coexistence of a phase transfer catalyst, if necessary.

[0307] Examples of the catalyst include palladium complexes such as bis(triphenylphosphine)palladium(II) dichloride, bis(tris-o-methoxyphenylphosphine)palladium(II) dichloride, tetrakis(triphenylphosphine)palladium(0), tris(dibenzylideneacetone)dipalladium(0), and palladium acetate; transition metal complexes such as tetrakis(triphenylphosphine)nickel(0), [1,3-bis(diphenylphosphino)propane)nickel(II) dichloride, and bis(1,4-cyclooctadiene)nickel(0); and complexes of these transition metal complexes further having ligands such as triphenylphosphine, tri(o-tolyl)phosphine, tri(tert-butyl)phosphine, tricyclohexylphosphine, 1,3-bis(diphenylphosphino)propane, and bipyridyl. The catalyst may be used alone or in combination of two or more.

[0308] The amount of the catalyst used is usually 0.00001 to 3 molar equivalents in terms of the amount of transition metal relative to the total number of moles of the raw material monomers.

[0309] Examples of the base and phase transfer catalyst include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, potassium fluoride, cesium fluoride, tripotassium phosphate, etc.; organic bases such as tetrabutylammonium fluoride, tetraethylammonium hydroxide, tetrabutylammonium hydroxide, etc.; and phase transfer catalysts such as tetrabutylammonium chloride, tetrabutylammonium bromide, etc. The base and phase transfer catalyst may each be used alone or in combination of two or more kinds.

[0310] The amount of the base and the phase transfer catalyst used is usually 0.001 to 100 molar equivalents relative to the total number of moles of the raw material monomers.

[0311] Examples of the solvent include organic solvents such as toluene, xylene, mesitylene, tetrahydrofuran, 1,4-dioxane, dimethoxyethane, N,N-dimethylacetamide, and N,N-dimethylformamide, and water. The solvent may be used alone or in combination of two or more.

[0312] The amount of the solvent used is usually 10 to 100,000 parts by mass per 100 parts by mass of the total of the raw material monomers.

[0313] The reaction temperature of the condensation polymerization is usually −100 to 200° C. The reaction time of the condensation polymerization is usually 1 hour or longer.

[0314] Post-treatment of the polymerization reaction can be carried out by any of the known methods, for example, a method of removing water-soluble impurities by liquid separation, a method of adding the reaction liquid after the polymerization reaction to a lower alcohol such as methanol, filtering the precipitate, and then drying the precipitate, or a combination of these methods. When the purity of the polymer compound is low, it can be purified by a normal method such as crystallization, reprecipitation, continuous extraction using a Soxhlet extractor, column chromatography, etc.

[0315] <Composition> The composition of the present embodiment contains at least one material selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, an antioxidant, and a solvent, and the polymer compound of the present embodiment.

[0316] A composition containing the polymer compound of this embodiment and a solvent (hereinafter, sometimes referred to as "ink") is suitable for producing a light-emitting device using a printing method such as inkjet printing or nozzle printing.

[0317] The viscosity of the ink may be adjusted depending on the type of printing method; however, when applied to a printing method in which the solution passes through a discharge device, such as inkjet printing, the viscosity is preferably 1 to 20 mPa s at 25°C to prevent clogging and deflection during discharge.

[0318] The solvent contained in the ink is preferably a solvent capable of dissolving or uniformly dispersing the solid content 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, mesitylene, ethylbenzene, n-hexylbenzene, and cyclohexylbenzene; cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane, n-dodecane, and bicyclohexyl. Examples of the solvent include aliphatic hydrocarbon solvents such as acetone, methyl ethyl ketone, cyclohexanone, acetophenone, and the like; ester solvents such as ethyl acetate, butyl acetate, ethyl cellosolve acetate, methyl benzoate, phenyl acetate, and the like; polyhydric alcohol solvents such as ethylene glycol, glycerin, 1,2-hexanediol, and the like; alcohol solvents such as isopropyl alcohol, cyclohexanol, and the like; sulfoxide solvents such as dimethyl sulfoxide, and the like; and amide solvents such as N-methyl-2-pyrrolidone, N,N-dimethylformamide, and the like. The solvents may be used alone or in combination of two or more kinds.

[0319] The amount of the solvent in the ink is usually 1,000 to 100,000 parts by mass, and preferably 2,000 to 20,000 parts by mass, per 100 parts by mass of the polymer compound of this embodiment.

[0320] [Hole transport material] The hole transport material is classified into a low molecular weight compound and a polymeric compound, and is preferably a polymeric compound, and more preferably a polymeric compound having a crosslinking group.

[0321] Examples of the polymeric compound include polyvinylcarbazole and its derivatives; polyarylenes having an aromatic amine structure in the side chain or main chain and its derivatives. The polymeric compound may be a compound to which an electron-accepting moiety is bonded. Examples of the electron-accepting moiety include fullerene, tetrafluorotetracyanoquinodimethane, tetracyanoethylene, trinitrofluorenone, etc., and fullerene is preferred.

[0322] In the composition of this embodiment, the amount of the hole transport material is usually 1 to 400 parts by mass, and preferably 5 to 150 parts by mass, based on 100 parts by mass of the polymer compound of this embodiment.

[0323] The hole transport material may be used alone or in combination of two or more kinds.

[0324] [Electron transport material] 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.

[0325] Examples of low molecular weight compounds include metal complexes having 8-hydroxyquinoline as a ligand, oxadiazole, anthraquinodimethane, benzoquinone, naphthoquinone, anthraquinone, tetracyanoanthraquinodimethane, fluorenone, diphenyldicyanoethylene, and diphenoquinone, as well as derivatives thereof.

[0326] Examples of the polymer compound include polyphenylene, polyfluorene, and derivatives thereof. The polymer compound may be doped with a metal.

[0327] In the composition of this embodiment, the amount of the electron transport material is usually 1 to 400 parts by mass, and preferably 5 to 150 parts by mass, based on 100 parts by mass of the polymer compound of this embodiment.

[0328] The electron transporting materials may be used alone or in combination of two or more kinds.

[0329] [Hole injection material and electron injection material] The hole injection material and the electron injection material are classified into low molecular weight compounds and high molecular weight compounds, respectively. The hole injection material and the electron injection material may have a crosslinking group.

[0330] Examples of low molecular weight compounds include metal phthalocyanines 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.

[0331] Examples of the polymer compound include polyaniline, polythiophene, polypyrrole, polyphenylene vinylene, polythienylene vinylene, polyquinoline, and polyquinoxaline, as well as derivatives thereof; and conductive polymers such as polymers containing an aromatic amine structure in the main chain or side chain.

[0332] In the composition of this embodiment, the amount of the hole injection material and the electron injection material is usually 1 to 400 parts by mass, and preferably 5 to 150 parts by mass, per 100 parts by mass of the polymer compound of this embodiment.

[0333] The hole injection material and the electron injection material may each be used alone or in combination of two or more kinds.

[0334] [Ion doping] When the hole injection material or the electron injection material includes a conductive polymer, the electrical conductivity of the conductive polymer is preferably 1×10 -5 S / cm~1×10 3 In order to set the electrical conductivity of the conductive polymer in this range, the conductive polymer can be doped with an appropriate amount of ions.

[0335] The type of ion to be doped is an anion for a hole injection material, and a cation for an electron injection material. Examples of the anion include polystyrene sulfonate ion, alkylbenzene sulfonate ion, and camphor sulfonate ion. Examples of the cation include lithium ion, sodium ion, potassium ion, and tetrabutylammonium ion. The ion to be doped may be one type or two or more types.

[0336] [Luminescent materials] The light-emitting materials are classified into low molecular weight compounds and high molecular weight compounds. The light-emitting materials may have a crosslinking group.

[0337] Examples of low molecular weight compounds include naphthalene and its derivatives, anthracene and its derivatives, perylene and its derivatives, and triplet luminescent complexes having iridium, platinum, or europium as a central metal.

[0338] Examples of the polymer compound include polymer compounds containing a phenylene group, a naphthalenediyl group, a fluorenediyl group, a phenanthrenediyl group, a dihydrophenanthrenediyl group, a group represented by the above formula (X), a carbazolediyl group, a phenoxazinediyl group, a phenothiazinediyl group, an anthracenediyl group, a pyrenediyl group, and the like.

[0339] The polymer compound is preferably a polymer compound containing a constitutional unit represented by the above formula (X) or (Y) since the light-emitting device has a better luminous efficiency. Examples and preferred ranges of the constitutional unit represented by formula (X) that the polymer compound may contain are the same as the examples and preferred ranges of the constitutional unit represented by formula (X). Examples and preferred ranges of the constitutional unit represented by formula (Y) that the polymer compound may contain are the same as the examples and preferred ranges of the constitutional unit represented by formula (Y).

[0340] The number average molecular weight of the polymer compound in terms of polystyrene is preferably 5×10 3 ~1×10 6 and more preferably 1×10 4 ~5×10 5 and more preferably 5×10 4 ~2×10 5 The weight average molecular weight of the polymer compound in terms of polystyrene is preferably 1×10 4 ~2×10 6 and more preferably 2×10 4 ~1×10 6 and more preferably 1×10 5 ~5×10 5 It is.

[0341] The polymer compound may be any one of a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, or other forms, but is preferably a copolymer obtained by copolymerizing a plurality of raw material monomers.

[0342] The light-emitting material may include low molecular weight compounds and high molecular weight compounds, and preferably includes triplet light-emitting complexes and high molecular weight compounds.

[0343] The triplet light-emitting complex is preferably an iridium complex such as a metal complex represented by the above formula (2), and more preferably an iridium complex such as a metal complex represented by formula (1-B1) to formula (1-B5), formula Ir-1 or formula Ir-2.

[0344] [ka] [In the formula, R D21 , R D22 , R D23 , R D24 , R D25 and R D26 , and R D31 , R D32 , R D33 , R D34 , R D35 , R D36 and R D37 R 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, or a halogen atom, and these groups may have a substituent. D21 , R D22 , R D23 , R D24 , R D25 and R D26 , and R D31 , R D32 , R D33 , R D34 , R D35 , R D36 and R D37 When multiple are present, they may be the same or different. -A D1 ---A D2 - represents an anionic bidentate ligand, A D1 and A D2 each independently represents a carbon atom, an oxygen atom, or a nitrogen atom bonded to an iridium atom, and these atoms may be atoms constituting a ring. D1 ---A D2 When multiple -s are present, they may be the same or different. n D1 represents 1, 2 or 3; n D2 represents 1 or 2.]

[0345] The preferred range of the iridium complex such as the metal complex represented by the above formula (2), which is the light emitting material of this embodiment, is the same as the preferred range of the iridium complex such as the metal complex represented by the above formula (2).

[0346] In the metal complex represented by formula Ir-1, preferably R D21 ~R D26 At least one of these is a group represented by the above formula (DA).

[0347] In the metal complex represented by formula Ir-2, preferably R D31 ~R D37 At least one of these is a group represented by the above formula (DA).

[0348] In the group represented by formula (DA) contained in the iridium complex such as the metal complex which is the light-emitting material of the present embodiment, m DA1 ~m DA3 is usually an integer of 10 or less, preferably an integer of 5 or less, and more preferably 0 or 1. DA1 ~m DA3 are preferably the same integer.

[0349] In the group represented by formula (DA) contained in the iridium complex such as the metal complex which is the light-emitting material of the present embodiment, DA is preferably a group represented by formula (GDA-11) to formula (GDA-15), and these groups may have a substituent.

[0350] [ka] [In the formula, *, ** and *** are Ar DA1 , Ar DA2 and Ar DA3 Represents a bond with. R DA R 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 further have a substituent. DAWhen there are multiple, they may be the same or different.

[0351] R DA is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group or a cycloalkoxy group, more preferably a hydrogen atom, an alkyl group or a cycloalkyl group, and these groups may have a substituent.

[0352] Ar DA1 ~Ar DA3 is preferably a group represented by formula (ArDA-1) to formula (ArDA-3), in which * represents the bonding position.

[0353] [ka] [In the formula, R DA has the same meaning as above. R DB 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. DB When there are multiple, they may be the same or different.

[0354] T DA is preferably a group represented by formula (TDA-1) to formula (TDA-3), in which * represents the bonding position.

[0355] [ka] [In the formula, R DA and R DB has the same meaning as above.]

[0356] In the group represented by formula (DA) contained in the iridium complex such as the metal complex serving as the luminescent material of this embodiment, the group represented by formula (DA) is preferably a group represented by formulae (D-A1) to (D-A3), where * represents a bonding position.

[0357] [ka] [In the formula, R p1 , R p2 and R p3 R each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or a halogen atom. p1 and R p2 When there are multiple, they may be the same or different. np1 represents an integer of 0 to 5, np2 represents an integer of 0 to 3, and np3 represents 0 or 1. A plurality of np1 may be the same or different.

[0358] np1 is preferably an integer of 0 to 3, more preferably an integer of 1 to 3, and further preferably 1. np2 is preferably 0 or 1, and more preferably 0. np3 is preferably 0.

[0359] R p1 , R p2 and R p3 is preferably an alkyl group or a cycloalkyl group.

[0360] -A D1 ---A D2 Examples of the anionic bidentate ligand represented by - and the preferred range thereof are represented by A 1 -G 1 -A 2 The examples and preferred ranges of the structural unit represented by the formula (I) are the same as those of the structural unit represented by the formula (I).

[0361] The iridium complexes such as metal complexes which are the luminescent material of this embodiment are preferably metal complexes represented by formulae Ir-11 to Ir-13, Ir-21, or Ir-31 to Ir-33. The metal complexes represented by formulae Ir-1 are preferably metal complexes represented by formulae Ir-41 to Ir-43. The metal complexes represented by formulae Ir-2 are preferably metal complexes represented by formulae Ir-51 to Ir-53.

[0362] [ka]

[0363] [ka]

[0364] [ka]

[0365] [ka]

[0366] [ka] [In the formula, n D2 represents 1 or 2. D represents a group represented by the formula (DA). A plurality of D's may be the same or different. R DC 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. DC may be the same or different. R DD represents an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. DD may be the same or different.]

[0367] Examples of triplet light-emitting complexes include the metal complexes shown below.

[0368] [ka]

[0369] [ka]

[0370] [ka]

[0371] [ka]

[0372] [ka]

[0373] In the composition of this embodiment, the amount of the light emitting material is usually 0.1 to 400 parts by mass based on 100 parts by mass of the polymer compound of this embodiment.

[0374] The light-emitting materials may be used alone or in combination of two or more kinds.

[0375] [Host material] The composition of the present embodiment preferably further contains a host material having at least one function selected from hole injection, hole transport, electron injection, and electron transport, since the composition of the present embodiment provides a light-emitting device with superior luminous efficiency. The composition of the present embodiment may contain only one type of host material, or may contain two or more types of host materials.

[0376] The host material preferably does not contain metal atoms.

[0377] When the composition of the present embodiment further contains a host material, the amount of the host material is usually 1×10 2 Mass part~1×10 5 parts by mass, preferably 1×10 2 Mass part~1×10 4 parts by mass, more preferably 1×10 2 Mass part~1×103 parts by mass, more preferably 2×10 2 Mass part~8×10 2 Parts by mass.

[0378] Since the composition of this embodiment can be prepared by a wet method, the host material is preferably one that is soluble in a solvent capable of dissolving the composition of this embodiment.

[0379] When the composition of the present embodiment further comprises a host material, the host material and the light-emitting material of the present embodiment preferably interact physically, chemically, or electrically. This interaction makes it possible to improve or adjust, for example, the light-emitting properties, charge transport properties, or charge injection properties of the composition of the present embodiment. In a case where the composition of this embodiment further contains a host material, taking the light-emitting material as an example, the host material and the triplet light-emitting complex which is the light-emitting material electrically interact with each other, and electrical energy is efficiently transferred from the host material to the triplet light-emitting complex which is the light-emitting material, so that the triplet light-emitting complex which is the light-emitting material can emit light more efficiently, and the light-emitting efficiency of the light-emitting element of this embodiment is superior. From the above viewpoint, since the light-emitting element has better luminous efficiency, it is preferable that the absolute value of the energy level of the lowest triplet excited state of the host material is greater than the absolute value of the energy level of the lowest triplet excited state of the triplet light-emitting complex that is the light-emitting material.

[0380] Host materials are classified into low molecular weight compounds (low molecular weight hosts) and high molecular weight compounds (high molecular weight hosts), and the composition of the present embodiment may contain either of the host materials. Examples of the polymer host include polymer compounds that are hole transport materials, which will be described later, and polymer compounds that are electron transport materials, which will be described later.

[0381] [Small molecule host] The low molecular weight host is preferably a compound represented by formula (H-1) since the light emitting device has a higher luminous efficiency.

[0382] [ka]

[0383] The molecular weight of the compound represented by formula (H-1) is preferably 1×10 2 ~5×10 3 and more preferably 2×10 2 ~3×10 3 and more preferably 3×10 2 ~1.5×10 3 and particularly preferably 4×10 2 ~1×10 3 It is.

[0384] Ar H1 and Ar H2In the above, examples of the aryl group and the monovalent heterocyclic group include groups in which one hydrogen atom directly bonded to an atom constituting the ring has been removed from benzene, naphthalene, anthracene, phenanthrene, dihydrophenanthrene, triphenylene, fluorene, benzofluorene, spirobifluorene, benzospirobifluorene, pyrene, chrysene, pyridine, diazabenzene, triazine, carbazole, azacarbazole, diazacarbazole, azanaphthalene, diazanaphthalene, dibenzofuran, dibenzothiophene, phenoxazine, phenothiazine, 9,10-dihydroacridine, 5,10-dihydrophenazine, azaanthracene, diazaanthracene, azaphenanthrene, diazaphenanthrene, indolocarbazole, or indenocarbazole. The aryl group and the monovalent heterocyclic group are preferably a group in which one hydrogen atom directly bonded to an atom constituting a ring is removed from benzene, naphthalene, anthracene, phenanthrene, fluorene, spirobifluorene, pyrene, pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, azacarbazole, dibenzofuran, dibenzothiophene, phenoxazine, phenothiazine, indolocarbazole, or indenocarbazole, more preferably a group in which one hydrogen atom directly bonded to an atom constituting a ring is removed from benzene, naphthalene, anthracene, fluorene, spirobifluorene, pyridine, diazabenzene, triazine, carbazole, dibenzofuran, or dibenzothiophene, and even more preferably a group in which one hydrogen atom directly bonded to an atom constituting a ring is removed from benzene or carbazole, and these groups may have a substituent.

[0385] Ar H1 and Ar H2The substituent that may be substituted is preferably a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, more preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and even more preferably an alkyl group or a cycloalkyl group, and these groups may further have a substituent. Ar H1 and Ar H2 Examples and preferred ranges of the aryl group and monovalent heterocyclic group in the substituent that may be possessed by Ar H1 and Ar H2 The examples and preferred ranges of the aryl group and monovalent heterocyclic group in are the same as those in the above. Ar H1 and Ar H2 In the substituted amino group in the substituent that may be carried by Ar, the substituent carried by the amino group is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups may further have a substituent. Examples and preferred ranges of the aryl group and the monovalent heterocyclic group in the substituent carried by the amino group are respectively, Ar H1 and Ar H2 The examples and preferred ranges of the aryl group and monovalent heterocyclic group in are the same as those in the above. Ar H1 and Ar H2 The substituent that the optionally substituted group may further have is preferably a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, more preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and even more preferably an alkyl group or a cycloalkyl group. These groups may further have a substituent, but preferably do not have a further substituent. Ar H1 and Ar H2 Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that may be further possessed by the substituent that may be possessed by Ar H1 and Ar H2The examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that may be possessed by are the same as those of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that may be possessed by the alkyl group.

[0386] n H1 is preferably 1. H2 is preferably 0. n H3 is usually an integer of 0 or more and 10 or less, preferably an integer of 0 or more and 5 or less, more preferably an integer of 1 or more and 3 or less, and even more preferably 2.

[0387] L H1 is preferably an arylene group or a divalent heterocyclic group, since this provides a light-emitting element with superior luminous efficiency.

[0388] L H1 Examples of L include groups in which two hydrogen atoms directly bonded to atoms constituting the ring have been removed from benzene, naphthalene, anthracene, phenanthrene, dihydrophenanthrene, triphenylene, fluorene, benzofluorene, spirobifluorene, benzospirobifluorene, pyrene, chrysene, pyridine, diazabenzene, triazine, carbazole, azacarbazole, diazacarbazole, azanaphthalene, diazanaphthalene, dibenzofuran, dibenzothiophene, phenoxazine, phenothiazine, 9,10-dihydroacridine, 5,10-dihydrophenazine, azaanthracene, diazaanthracene, azaphenanthrene, diazaphenanthrene, indolocarbazole, or indenocarbazole. H1is preferably a group obtained by removing two hydrogen atoms directly bonded to an atom constituting a ring from benzene, naphthalene, anthracene, phenanthrene, fluorene, spirobifluorene, pyrene, pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, azacarbazole, dibenzofuran, dibenzothiophene, phenoxazine, phenothiazine, indolocarbazole, or indenocarbazole, more preferably a group obtained by removing one hydrogen atom directly bonded to an atom constituting a ring from benzene, naphthalene, anthracene, fluorene, spirobifluorene, pyridine, diazabenzene, triazine, carbazole, dibenzofuran, or dibenzothiophene, even more preferably a group obtained by removing two hydrogen atoms directly bonded to an atom constituting a ring from benzene, naphthalene, anthracene, carbazole, dibenzofuran, or dibenzothiophene, and these groups may have a substituent.

[0389] L H1 The substituent that may be substituted is preferably a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, more preferably an alkyl group, an alkoxy group, an aryl group, or a monovalent heterocyclic group, and even more preferably an alkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may further have a substituent. L H1 Examples and preferred ranges of the aryl group, monovalent heterocyclic group, and substituted amino group in the substituent that may be possessed by Ar are respectively H1 and Ar H2 The examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that may be possessed by the group are the same as those of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that may be possessed by the group. L H1 Examples of the substituents that may be further substituted by the substituents that may be substituted by Ar H1 and Ar H2 The examples and preferred ranges of the substituents which may be further possessed by the group are the same as those of the substituents which may be further possessed by the group.

[0390] R H21 is preferably an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. R H21 The definitions and examples of the aryl group and monovalent heterocyclic group represented by the formula: H1 and Ar H2 The definitions and examples of the aryl group and monovalent heterocyclic group represented by the following formula are the same as those of the aryl group and monovalent heterocyclic group represented by the following formula: R H21 The definition and examples of the substituents that may be substituted by Ar H1 and Ar H2 The definition and examples of the substituents which may be possessed by are the same as those of the substituents which may be possessed by the group.

[0391] The compound represented by formula (H-1) is preferably a compound represented by formula (H-2).

[0392] [ka] [In the formula, Ar H1 , Ar H2 , n H3 and L H1 has the same meaning as above.]

[0393] Examples of the low molecular weight host material include the compound represented by the following formula and the compound HM1 described below.

[0394] [ka]

[0395] [ka]

[0396] [ka]

[0397] [ka]

[0398] In the formula, Z 2 represents an oxygen atom or a sulfur atom.

[0399] [Polymer host] Examples of the polymer host material include a polymer compound that is a hole transport material, which will be described later, and a polymer compound that is an electron transport material, which will be described later.

[0400] The number average molecular weight of the polymer host material in terms of polystyrene is preferably 5×10 3 ~1×10 6 and more preferably 1×10 4 ~5×10 5 and more preferably 5×10 4 ~2×10 5 The weight average molecular weight of the polymer host material in terms of polystyrene is preferably 1×10 4 ~2×10 6 and more preferably 2×10 4 ~1×10 6 and more preferably 1×10 5 ~5×10 5 It is. The polymer host material may be any one of a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, or other forms, but is preferably a copolymer obtained by copolymerizing a plurality of raw material monomers.

[0401] The polymer host material is preferably a polymer compound containing a structural unit represented by the above formula (X) or the above formula (Y) since the light-emitting device has a better luminous efficiency. Examples and preferred ranges of the structural unit represented by formula (X) that the polymer host material may contain are the same as the examples and preferred ranges of the structural unit represented by formula (X). Examples and preferred ranges of the structural unit represented by formula (Y) that the polymer host material may contain are the same as the examples and preferred ranges of the structural unit represented by formula (Y).

[0402] [Antioxidants] The antioxidant may be any compound that is soluble in the same solvent as the polymer compound of this embodiment and does not inhibit light emission and charge transport, and examples of such antioxidants include phenol-based antioxidants and phosphorus-based antioxidants.

[0403] In the composition of this embodiment, the blending amount of the antioxidant is usually 0.001 to 10 parts by mass with respect to 100 parts by mass of the polymer compound of this embodiment.

[0404] The antioxidants may be used alone or in combination of two or more.

[0405] <Membrane> The film may contain the polymer compound of this embodiment as it is, or may contain the polymer compound of this embodiment in a state of intramolecular or intermolecular, or intramolecular and intermolecular crosslinking (crosslinked product). The crosslinked product of the polymer compound may be a crosslinked product intermolecularly crosslinked between the polymer compound and another compound. The film containing the crosslinked product of the polymer compound is a film obtained by crosslinking the film containing the polymer compound by an external stimulus such as heating or light irradiation. The film containing the crosslinked product of the polymer compound is substantially insoluble in a solvent, and therefore can be suitably used for laminating light-emitting elements described later.

[0406] The heating temperature for crosslinking the film is usually 25 to 300°C, preferably 50 to 250°C, and more preferably 150 to 200°C, since this improves the luminous efficiency.

[0407] The type of light used for the light irradiation to crosslink the film is, for example, ultraviolet light, near ultraviolet light, or visible light.

[0408] The film is suitable as a hole transport layer or a hole injection layer in a light emitting device.

[0409] The film can be produced using an ink by, for example, spin coating, casting, microgravure coating, gravure coating, bar coating, roll coating, wire bar coating, dip coating, spray coating, screen printing, flexographic printing, offset printing, inkjet printing, capillary coating, or nozzle coating.

[0410] The thickness of the film is usually from 1 nm to 10 μm.

[0411] <Light emitting element> The light-emitting device of this embodiment has an organic layer containing a crosslinked product of the polymer compound of this embodiment. The light-emitting element of this embodiment has, for example, electrodes consisting of an anode and a cathode, and an organic layer containing a crosslinked body of the polymer compound of this embodiment provided between the electrodes.

[0412] [Layer composition] The organic layer containing the crosslinked polymer compound of the present embodiment is usually one or more layers selected from the group consisting of a light-emitting layer, a hole-transporting layer, a hole-injecting layer, an electron-transporting layer, and an electron-injecting layer, and is preferably a hole-transporting layer. Each of these layers contains a light-emitting material, a hole-transporting material, a hole-injecting material, an electron-transporting material, and an electron-injecting material. Each of these layers can be formed by dissolving the light-emitting material, the hole-transporting material, the hole-injecting material, the electron-transporting material, and the electron-injecting material in the above-mentioned solvent to prepare an ink, and using the ink, using the same method as for producing the above-mentioned film.

[0413] The light-emitting element has a light-emitting layer between an anode and a cathode, and the light-emitting layer is preferably provided between an organic layer and the cathode. From the viewpoint of hole injection and hole transport properties, the light-emitting element preferably has at least one layer of a hole injection layer and a hole transport layer between the anode and the light-emitting layer, and from the viewpoint of electron injection and electron transport properties, the light-emitting element preferably has at least one layer of an electron injection layer and an electron transport layer between the cathode and the light-emitting layer. Materials for the hole transport layer, electron transport layer, light-emitting layer, hole injection layer, and electron injection layer include the polymer compound of this embodiment as well as the hole transport material, electron transport material, light-emitting material, hole injection material, and electron injection material described above, respectively.

[0414] When the material of the hole transport layer, the material of the electron transport layer, and the material of the light-emitting layer are soluble in a solvent used for forming the hole transport layer, the electron transport layer, and the layer adjacent to the light-emitting layer in the preparation of the light-emitting element, the material preferably has a crosslinking group in order to prevent the material from dissolving in the solvent. After forming each layer using a material having a crosslinking group, the layer can be insolubilized by crosslinking the crosslinking group.

[0415] In the light-emitting element of the present embodiment, examples of the method for forming each layer, such as the light-emitting layer, hole transport layer, electron transport layer, hole injection layer, and electron injection layer, include, when a low molecular weight compound is used, a vacuum deposition method from a powder, and a method of film formation from a solution or molten state. When a high molecular weight compound is used, examples of the method include a method of film formation from a solution or molten state.

[0416] The order, number and thickness of the layers to be laminated may be adjusted taking into consideration the light emission efficiency and device life.

[0417] When the light-emitting element of the present embodiment has an electron transport layer, the electron transport material contained in the electron transport layer may be a low molecular weight compound or a polymer compound. The electron transport material contained in the electron transport layer is preferably a polymer compound. The polymer compound contained in the electron transport layer is preferably a polymer compound containing at least one structural unit selected from the group consisting of structural units represented by formula (ET-1) and structural units represented by formula (ET-2) (hereinafter, also referred to as "polymer compound of electron transport layer").

[0418] [ka] [In the formula, nE1 represents an integer of 1 or more. Ar E1 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups are R E1 It may have a substituent other than the above. R E1 R represents a group represented by formula (ES-1). E1 When multiple are present, they may be the same or different.

[0419] [ka] [In the formula, nE3 represents an integer of 0 or more, aE1 represents an integer of 1 or more, bE1 represents an integer of 0 or more, and mE1 represents an integer of 1 or more. When multiple nE3, aE1, and bE1 are present, they may be the same or different. However, R E3 is a single bond, mE1 is 1. In addition, aE1 and bE1 are selected so that the charge of the group represented by formula (ES-1) is 0. R E3 is a single bond, a hydrocarbon group, a heterocyclic group, or -OR E3 '- represents (R E3 represents a hydrocarbon group or a heterocyclic group, and these groups may have a substituent. Q E1 represents an alkylene group, a cycloalkylene group, an arylene group, an oxygen atom or a sulfur atom, and these groups may have a substituent. Q E1 When multiple are present, they may be the same or different. Y E1 -CO2 - , -SO3 - , -SO2 - or -PO3 2- Represents Y. E1 When multiple are present, they may be the same or different. M E1 represents an alkali metal cation, an alkaline earth metal cation or an ammonium cation, and this ammonium cation may have a substituent. M E1When multiple are present, they may be the same or different. Z E1 is F - , Cl - , Br - , I - , O.H. - , B(R E4 )4 - , R E4 SO3 - , R E4 COO - , NO3 - , SO4 2- , HSO4 - , PO4 3- , HPO4 2- , H2PO4 - , BF4 - or PF6 - Represents R E4 represents an alkyl group, a cycloalkyl group or an aryl group, and these groups may have a substituent. E1 When multiple are present, they may be the same or different.

[0420] nE1 is usually an integer of 1 to 4, and preferably 1 or 2.

[0421] Ar E1 is preferably a group in which nE1 hydrogen atom directly bonded to an atom constituting the ring has been removed from a 1,4-phenylene group, a 1,3-phenylene group, a 1,2-phenylene group, a 2,6-naphthalenediyl group, a 1,4-naphthalenediyl group, a 2,7-fluorenediyl group, a 3,6-fluorenediyl group, a 2,7-phenanthrenediyl group, or a 2,7-carbazolediyl group, and R E1 It may have a substituent other than the above.

[0422] Ar E1 R may have E1Examples of the substituent other than the above include a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an amino group, a substituted amino group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a cycloalkynyl group, a carboxyl group, and a group represented by formula (ES-3). -O-(C n’ H 2n’ O) nx -C m’ H 2m’+1 (ES-3) [In the formula, n', m', and nx each independently represent an integer of 1 or more.]

[0423] nE3 is usually an integer of 0 to 10, preferably an integer of 0 to 8, and more preferably an integer of 0 to 2.

[0424] aE1 is usually an integer of 1 to 10, preferably an integer of 1 to 5, and more preferably 1 or 2.

[0425] bE1 is usually an integer of 0 to 10, preferably an integer of 0 to 4, and more preferably 0 or 1.

[0426] mE1 is usually an integer of 1 to 5, preferably 1 or 2, and more preferably 0 or 1.

[0427] R E3 -OR E3 In the case of '-, the group represented by formula (ES-1) is a group represented by the following formula:

[0428] [ka]

[0429] R E3 is preferably a hydrocarbon group or a heterocyclic group, more preferably an aromatic hydrocarbon group or an aromatic heterocyclic group, and further preferably an aromatic hydrocarbon group.

[0430] R E3 Examples of the substituent that may be possessed by R include an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, and a group represented by the formula (ES-3). E3 The substituent that may be possessed by is preferably a group represented by formula (ES-3).

[0431] Q E1 is preferably an alkylene group, an arylene group, or an oxygen atom, and more preferably an alkylene group or an oxygen atom.

[0432] Y E1 -CO2 - , -SO2 - or PO3 2- It is preferable that -CO2 - It is more preferable that:

[0433] M E1 Examples of the alkali metal cation represented by the formula: + , Na + , K + , Rb + , Cs + Examples include: E1 The alkali metal cation represented by K + , Rb + Or Cs + It is preferable that Cs + It is more preferable that:

[0434] M E1 Examples of the alkaline earth metal cation represented by the formula: 2+ , Mg 2+ , Ca 2+ , Sr 2+ , B.A. 2+ Examples include: E1 The alkaline earth metal cation represented by 2+ , Ca 2+ , Sr 2+ Or Ba 2+ Preferably, Ba 2+ It is more preferable that:

[0435] M E1 is preferably an alkali metal cation or an alkaline earth metal cation, more preferably an alkali metal cation.

[0436] Z E1 is F - , Cl - , Br - , I - , O.H. - , B(R E4 )4 - , R E4 SO3 - , R E4 COO - Or NO3 - Preferably, F - , Cl - , Br - , I - , O.H. - , R E4 SO3 - or R E4 COO - It is more preferable that R E4 is preferably an alkyl group.

[0437] Examples of the group represented by formula (ES-1) include groups represented by the following formulas.

[0438] [ka]

[0439] [ka] [In the formula, M + Li + , Na + , K + , Cs + or N(CH3)4 + Represents M + When multiple are present, they may be the same or different.

[0440] [ka] [In the formula, nE2 represents an integer of 1 or more. Ar E2 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups are R E2 It may have a substituent other than the above. R E2 R represents a group represented by formula (ES-2). E2 When multiple are present, they may be the same or different.

[0441] [ka] [In the formula, nE4 represents an integer of 0 or more, aE2 represents an integer of 1 or more, bE2 represents an integer of 0 or more, and mE2 represents an integer of 1 or more. When a plurality of nE4, aE2, and bE2 ​​are present, they may be the same or different. However, R E5 When is a single bond, mE2 is 1. In addition, aE2 and bE2 ​​are selected so that the charge of the group represented by formula (ES-2) is 0. R E5 is a single bond, a hydrocarbon group, a heterocyclic group, or -OR E5 '- represents (R E5 represents a hydrocarbon group or a heterocyclic group, and these groups may have a substituent. Q E2 represents an alkylene group, a cycloalkylene group, an arylene group, an oxygen atom or a sulfur atom, and these groups may have a substituent. Q E2 When multiple are present, they may be the same or different. Y E2 -C + R E6 2, -N + R E6 3, -P + R E6 3, -S + R E6 2 or -I+ R E6 Represents 2. R E6 represents a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, and these groups may have a substituent. E6 may be the same or different. Y E2 When multiple are present, they may be the same or different. M E2 is F - , Cl - , Br - , I - , O.H. - , B(R E7 )4 - , R E7 SO3 - , R E7 COO - , BF4 - , SbCl6 - or SbF6 - Represents R E7 represents an alkyl group, a cycloalkyl group or an aryl group, and these groups may have a substituent. M E2 When multiple are present, they may be the same or different. Z E2 represents an alkali metal cation or an alkaline earth metal cation. E2 When multiple are present, they may be the same or different.

[0442] nE2 is usually an integer of 1 to 4, and preferably 1 or 2.

[0443] Ar E2 is preferably a group in which nE2 hydrogen atoms directly bonded to atoms constituting the ring have been removed from a 1,4-phenylene group, a 1,3-phenylene group, a 1,2-phenylene group, a 2,6-naphthalenediyl group, a 1,4-naphthalenediyl group, a 2,7-fluorenediyl group, a 3,6-fluorenediyl group, a 2,7-phenanthrenediyl group, or a 2,7-carbazolediyl group, and R E2 It may have a substituent other than the above.

[0444] Ar E2 R may have E2 The substituents other than Ar E1 R may have E1 The same applies to the substituents other than the above.

[0445] nE4 is usually an integer of 0 to 10, preferably an integer of 0 to 8, and more preferably an integer of 0 to 2.

[0446] aE2 is usually an integer of 1 to 10, preferably an integer of 1 to 5, and more preferably 1 or 2.

[0447] bE2 is usually an integer of 0 to 10, preferably an integer of 0 to 4, and more preferably 0 or 1.

[0448] mE2 is usually an integer of 1 to 5, preferably 1 or 2, and more preferably 0 or 1.

[0449] R E5 -OR E5 In the case of (ES-2), the group represented by formula (ES-2) is a group represented by the following formula:

[0450] [ka]

[0451] R E5 is preferably a hydrocarbon group or a heterocyclic group, more preferably an aromatic hydrocarbon group or an aromatic heterocyclic group, and further preferably an aromatic hydrocarbon group.

[0452] R E5 Examples of the substituent that may be possessed by R include an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, and a group represented by the formula (ES-3). E5 The substituent that may be possessed by is preferably a group represented by formula (ES-3).

[0453] Q E2 is preferably an alkylene group, an arylene group, or an oxygen atom, and more preferably an alkylene group or an oxygen atom.

[0454] Y E2 -C + R E6 2, -N + R E6 3, -P + R E6 3 or -S + R E6 2 is preferred, -N + R E6 More preferably, R is 3. E6 is preferably a hydrogen atom, an alkyl group, or an aryl group, and more preferably a hydrogen atom or an alkyl group.

[0455] M E2 is F - , Cl - , Br - , I - , B(R E7 )4 - , R E7 SO3 - , R E7 COO - , BF4 - or SbF 6- Preferably, Br - , I - , B(R E7 )4 - , R E7 COO - or SbF 6- It is more preferable that R E7 is preferably an alkyl group.

[0456] Z E2 Examples of the alkali metal cation represented by the formula: + , Na + , K + , Rb + , Cs + Z E2 The alkali metal cation represented by Li +, Na + Or K + It is preferable that:

[0457] Z E2 Examples of the alkaline earth metal cation represented by the formula: 2+ , Mg 2+ , Ca 2+ , Sr 2+ , B.A. 2+ Z E2 The alkaline earth metal cation represented by 2+ or Ca 2+ It is preferable that:

[0458] Z E2 is preferably an alkali metal cation.

[0459] Examples of the group represented by formula (ES-2) include groups represented by the following formulas.

[0460] [ka]

[0461] [ka] [In the formula, X - is F - , Cl - , Br - , I - , B(C6H5)4 - , CH3COO - or CF3SO3 - Represents X. - When multiple are present, they may be the same or different.

[0462] Examples of the constitutional unit represented by formula (ET-1) or (ET-2) include constitutional units represented by formulas (ET-31) to (ET-38).

[0463] [ka]

[0464] [ka]

[0465] [ka]

[0466] The polymer compound of the electron transport layer can be synthesized according to the methods described in, for example, JP-A-2009-239279, JP-A-2012-033845, JP-A-2012-216821, JP-A-2012-216822, and JP-A-2012-216815.

[0467] [Substrate / electrode] The substrate in the light-emitting element may be any substrate on which an electrode can be formed and which is not chemically changed when an organic layer is formed, and may be made of a material such as glass, plastic, silicon, etc. In the case of an opaque substrate, it is preferable that the electrode furthest from the substrate is transparent or semi-transparent.

[0468] The anode material may be, for example, a conductive metal oxide or a translucent metal. The anode material is 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, or copper.

[0469] Examples of the cathode material 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 metals; alloys of one or more of these metals with one or more of silver, copper, manganese, titanium, cobalt, nickel, tungsten, and tin; and graphite and graphite intercalation compounds. Examples of the alloys include 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. The anode and the cathode may each have a laminated structure of two or more layers.

[0470] [Application] The light-emitting element of this embodiment is useful for, for example, displays and lighting. EXAMPLES

[0471] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.

[0472] In the examples, the polystyrene-equivalent number average molecular weight (Mn) and polystyrene-equivalent weight average molecular weight (Mw) of the polymer compound were determined by size exclusion chromatography (SEC) using tetrahydrofuran as the mobile phase under the following measurement conditions.

[0473] The polymer compound to be measured was dissolved in tetrahydrofuran at a concentration of about 0.05% by mass, and 10 μL was injected into the SEC. The mobile phase was run at a flow rate of 1.0 mL / min. The column used was PLgel MIXED-B (manufactured by Polymer Laboratories). The detector used was a UV-VIS detector (manufactured by Tosoh, product name: UV-8320GPC).

[0474] LC-MS was measured by the following method. The measurement 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, product name: 1100LCMSD). The mobile phase of LC-MS was a mixture of acetonitrile and tetrahydrofuran, with the ratio being varied, and the flow rate was 0.2 mL / min. The column used was L-column 2 ODS (3 μm) (Chemicals Evaluation and Research Institute, Inc., inner diameter: 2.1 mm, length: 100 mm, particle size: 3 μm).

[0475] TLC-MS was measured by the following method. The measurement sample was dissolved in any of the solvents, toluene, tetrahydrofuran, or chloroform, at an arbitrary concentration, applied to a TLC plate for DART (manufactured by Techno Applications, product name: YSK5-100), and measured using a TLC-MS (manufactured by JEOL, product name: JMS-T100TD (The AccuTOF TLC)). The helium gas temperature during the measurement was adjusted in the range of 200 to 400°C.

[0476] NMR was measured by the following method. 5 to 10 mg of a measurement sample was dissolved in approximately 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 methylene chloride, and measurement was performed using an NMR device (manufactured by Agilent, trade name: INOVA300 or MERCURY 400VX).

[0477] As an index of the purity of the compound, the value of the area percentage of high performance liquid chromatography (HPLC) was used. This value is the value at UV=254 nm in HPLC (manufactured by Shimadzu Corporation, product name: LC-20A) unless otherwise specified. In this case, the compound to be measured was dissolved in tetrahydrofuran or chloroform so as to have a concentration of 0.01 to 0.2 mass%, and 1 to 10 μL was injected into the HPLC depending on the concentration. The mobile phase of the HPLC was used with a ratio of acetonitrile / tetrahydrofuran changed from 100 / 0 to 0 / 100 (volume ratio), and was run at a flow rate of 1.0 mL / min. The column used was Kaseisorb LC ODS 2000 (manufactured by Tokyo Chemical Industry Co., Ltd.) or an ODS column having equivalent performance. The detector used was a photodiode array detector (manufactured by Shimadzu Corporation, product name: SPD-M20A).

[0478] <Synthesis of Compounds> Compounds S1 to S27, compound HM1, compound COM-35, compound COM-3, compound COM-7, compound MC1, compound MC2 and compound ETL1 in the following examples and comparative examples were synthesized as follows.

[0479] Synthesis of compound S1

[0480] [ka]

[0481] (Compound 1a) After the inside of the reaction vessel was filled with argon gas, tris(dibenzylideneacetone)dipalladium (7.7 g), tri-tert-butylphosphine tetrafluoroborate (7.6 g), sodium tert-butoxide (167.8 g), and toluene (2800 mL) were added and stirred, and 2-(4-bromophenyl)-1,3-dioxolane (45.6 g) and aniline (105.7 g) were added thereto, and the mixture was stirred while being heated in an oil bath at 55° C. for 4 hours. After the reaction solution was cooled to room temperature, ion-exchanged water (2000 mL) was added and stirred. The obtained solution was washed twice with ion-exchanged water (2000 mL), and the obtained organic phase was dried with magnesium sulfate, after which activated carbon (42 g) was added, stirred for 10 minutes, filtered through a filter covered with Celite, and the residue was washed with toluene (1000 mL). The obtained filtrate was concentrated under reduced pressure. The obtained crude product was dissolved in a mixed solvent of toluene and ethyl acetate, and purified by filtering through a filter covered with aminosilica and celite. The obtained crude product was recrystallized multiple times with a mixed solvent of hexane and ethyl acetate. The obtained white solid was dried under reduced pressure at 50°C to obtain compound 1a (170.6 g, white solid). The GC area percentage of compound 1a was 98.6% or more. 1 H-NMR(CD2Cl2,400MHz):δ(ppm)=7.31(d,2H),7.25(t,2H),7.07(d,2H),7.03(d,2H) ,6.92(t,1H),5.86(brord-s,1H),5.66(s,1H),4.12-4.02(m,2H),4.01-3.91(m,2H). TLC-MS (ESI, positive): [M+H] + 241.

[0482] (Compound 1b) After the inside of the reaction vessel was filled with argon gas, compound 1a (91.5 g), 2,7-dibromo-9,9-di-n-octylfluorene (90.43 g), tris(dibenzylideneacetone)dipalladium (4.9 g), tri-tert-butylphosphine tetrafluoroborate (4.8 g), sodium tert-butoxide (47.5 g), toluene (1990 mL), and tert-butanol (1990 mL) were added and stirred while heating in an oil bath at 60 ° C. for 2 hours. After cooling the reaction solution to room temperature, ion-exchanged water (915 mL) was added and stirred. The obtained solution was washed twice with ion-exchanged water (915 mL), and the obtained organic phase was dried with magnesium sulfate, and then activated carbon (29 g) was added, stirred for 10 minutes, filtered with a filter covered with Celite, and the filtered product was washed with toluene (458 mL). The obtained filtrate was concentrated under reduced pressure to obtain Compound 1b (183.4 g, brown oil). The LC area percentage of Compound 1b was 89.8% or more. 1 H-NMR(CD2Cl2,400MHz):δ(ppm)=7.48(d,2H),7.28(d,4H),7.22(t,4H),7.10-6.92(m,14H),5.66(s,2H),4 .12-4.02(m,4H),4.01-3.91(m,4H),1.78-1.70(m,4H),1.27-0.95(m,20H),0.83(t,6H),0.70-0.59(m,4H). TLC-MS (ESI, positive): [M+H] + 870.

[0483] (Compound 1c) After the inside of the reaction vessel was filled with argon gas, compound 1b (160.0 g) and tetrahydrofuran (1600 mL) were added and stirred, and 2M hydrochloric acid (736 mL) was added thereto and stirred for 1 hour. Toluene (1200 mL) was added to the obtained solution and stirred. The obtained solution was washed three times with ion-exchanged water (800 mL), and the obtained organic phase was dried with magnesium sulfate, and then activated carbon (29 g) was added and stirred for 10 minutes, filtered with a filter covered with Celite, and the filtrate was washed with toluene (800 mL). The obtained filtrate was concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (mixed solvent of toluene and ethyl acetate). The obtained crude product was recrystallized several times with a mixed solvent of toluene and heptane. The obtained yellow solid was dried under reduced pressure at 50 ° C to obtain compound 1c (112.1 g, yellow solid). The LC area percentage of compound 1c was 99.9% or more. 1 H-NMR(CD2Cl2,400MHz):δ(ppm)=9.77(d,2H),7.66-7.56(m,6H),7.36-7.28(m,4H),7.21-7.12( m,8H),7.10-7.01(m,6H),1.83-1.74(m,4H),1.27-0.94(m,20H),0.82(t,6H),0.70-0.59(m,4H). LC-MS(ESI,positive):[M+H] + 782.

[0484] (Compound 1d) After the inside of the reaction vessel was filled with argon gas, compound 1c (105.0 g), chloroform (1365 mL), and N,N-dimethylformamide (735 mL) were added and stirred under ice cooling, and N-bromosuccinimide (47.9 g) was added thereto and stirred for 10 hours. 5% by mass aqueous sodium sulfite solution (420 mL) was added to the obtained solution and stirred. Chloroform (525 mL) and ion-exchanged water (525 mL) were added to the obtained solution, and the solution was washed twice with ion-exchanged water (525 mL), and the obtained solution was concentrated under reduced pressure. The obtained crude product was dissolved in toluene (525 mL) and washed twice with ion-exchanged water (525 mL). The obtained organic phase was dried over magnesium sulfate, and then activated carbon (25 g) was added and stirred for 10 minutes, and the mixture was filtered through a filter covered with Celite, and the filtrate was washed with toluene (525 mL). The obtained filtrate was concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (mixed solvent of heptane, toluene and ethyl acetate). The obtained crude product was recrystallized several times with a mixed solvent of toluene and acetonitrile. The obtained yellow solid was dried under reduced pressure at 50°C to obtain compound 1d (88.4 g, yellow solid). The LC area percentage of compound 1d was 99.9% or more. 1 H-NMR (CD2Cl2,400MHz): δ(ppm)=9.79(s,2H),7.67(d,4H),7.61(d,2H),7.42(d,4H),7.13(d,2 H),7.09-7.02(m,10H),1.83-1.74(m,4H),1.28-0.94(m,20H),0.82(t,6H),0.70-0.59(m,4H). LC-MS(ESI,positive):[M+H] + 939.

[0485] (Compound S1) After the inside of the reaction vessel was filled with argon gas, methyltriphenylphosphonium bromide (121.8 g) and toluene (960 mL) were added and stirred under ice cooling. Potassium tert-butoxide (38.2 g) was added thereto, and the mixture was warmed to room temperature and stirred for 2 hours, then cooled on ice. Compound 1d (80.0 g) and toluene (1200 mL) were added and stirred for 2 hours. Ion-exchanged water (800 mL) was added to the obtained solution and stirred. The obtained solution was washed twice with ion-exchanged water (400 mL), and the obtained organic phase was dried with magnesium sulfate. Thereafter, activated carbon (16 g) was added thereto and stirred for 10 minutes, filtered with a filter covered with alumina and celite, and the filtered product was washed with toluene (1600 mL). The obtained crude product was washed with 2-propanol. The obtained crude product was purified by alumina column chromatography (mixed solvent of heptane and toluene). The obtained crude product was recrystallized several times with a mixed solvent of toluene, heptane and 2-propanol. The obtained pale yellow solid was dried under reduced pressure at room temperature to obtain compound S1 (31.9 g, pale yellow solid). The LC area percentage of compound S1 was 99.7% or more. 1 H-NMR (CD2Cl2,400MHz):δ(ppm)=7.49(d,2H),7.31(d,4H),7.28(d,4H),7.06(d,2H),7.01(d,4H),6.95(d,6H), 6.65(dd,2H),5.63(d,2H),5.14(d,2H),1.80-1.71(m,4H),1.30-0.94(m,20H),0.82(t,6H),0.69-0.58(m,4H). LC-MS(ESI,positive):[M+H] + 935.

[0486] [ka]

[0487] Synthesis and acquisition of compounds S2 to S14 Compound S2 was synthesized according to the method described in JP-A-2008-517135. Compound S3 and compounds S6 to S9 were synthesized according to the method described in JP 2012-144722 A. Compound S4 was synthesized according to the method described in WO 2002-045184. Compound S5 and compound S11 were synthesized according to the method described in JP 2010-189630 A. Compound S10 used was a commercially available product. Compound S12 was synthesized according to the method described in WO2012-086671. Compounds S13 and S14 were synthesized according to the method described in JP 2015-086215 A.

[0488] [ka]

[0489] Synthesis of compounds S15 to S27 Compounds S15 to S17 were synthesized according to the method described in WO 2017-146083. Compounds S18, S21 and S26 were synthesized according to the method described in WO 2013-146806. Compound S19 was synthesized according to the method described in JP 2010-215886 A. Compound S20 was synthesized according to the method described in WO 2013 / 191088. Compound S22 was synthesized according to the method described in JP 2011-174062 A. Compound S23 was synthesized according to the method described in JP 2017-125087 A. Compound S24 was synthesized according to the method described in WO 2011 / 049241. Compound S25 was synthesized according to the method described in WO 2015 / 145871. Compound S27 was synthesized according to the method described in JP 2012-144722 A.

[0490] [ka]

[0491] Synthesis of compound HM1 Compound HM1 was synthesized according to the method described in WO 2018-199283.

[0492] [ka]

[0493] Synthesis of compounds COM-35, COM-3, COM-7 and MC1 Compound COM-35 was synthesized according to the methods described in WO 2016-046572 and WO 2018-199283. Compound COM-3 was synthesized according to the method described in WO 2009-131255. Compound COM-7 was synthesized according to the method described in JP 2011-105701 A. Compound MC1 was synthesized according to the method described in WO 2009-157424.

[0494] [ka]

[0495] Synthesis of compound MC2 Compound COM2 was synthesized according to the methods described in International Publication No. 2015-105014 and Japanese Patent Application Laid-Open No. 2011-105701.

[0496] [ka]

[0497] Synthesis of compound ETL1 Compound ETL1 was synthesized according to the method described in WO 2015 / 159932.

[0498] Example 1 <Synthesis of polymer compound P1> (Step 1) After the inside of a reaction vessel was filled with an inert gas atmosphere, the above compound S1 (1.082 g), the above compound S3 (1.029 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.01 mg) and toluene (33 mL) were added and heated to 80°C.

[0499] (Step 2) Then, a 20% by mass aqueous solution of tetraethylammonium hydroxide (16.6 g) was added dropwise to the reaction vessel, and the mixture was refluxed for 6 hours.

[0500] (Step 3) Thereafter, phenylboronic acid (70.3 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.01 mg) were added to a reaction vessel, and the mixture was stirred at 80° C. for 3 hours.

[0501] (Step 4) After cooling the obtained reaction mixture, an aqueous solution of sodium diethyldithiacarbamate was added and stirred at 40°C for 1 hour. The obtained reaction solution was cooled, the aqueous layer was removed, and the obtained organic layer was washed twice with 3% by mass aqueous ammonia and twice with water. The obtained solution was dropped into methanol and stirred, and a precipitate was generated. The obtained precipitate was dissolved in toluene (95 mL), alumina (59 g) was added, and the mixture was stirred for 3 hours. The obtained suspension was purified by passing it through a silica gel column. The obtained solution was dropped into methanol and stirred, and a precipitate was generated. The obtained precipitate was filtered and dried to obtain 1.01 g of polymer compound P1 of Example 1. The Mn of polymer compound P1 was 5.0 × 10 4 and Mw is 2.9 × 10 5 It was.

[0502] Based on theoretical values ​​calculated from the amounts of the raw materials charged, polymer compound P1 is presumed to be a copolymer composed of structural units derived from compound S1 and structural units derived from compound S3 in a molar ratio of 50:50.

[0503] Comparative Example 1 <Synthesis of polymer compound P2> (Step 1) After the inside of a reaction vessel was filled with an inert gas atmosphere, the above compound S2 (0.865 g), the above compound S3 (1.796 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.76 mg) and toluene (37 mL) were added and heated to 80°C.

[0504] (Step 2) Then, a 20% by mass aqueous solution of tetraethylammonium hydroxide (18.7 g) was added dropwise to the reaction vessel and refluxed for 6 hours.

[0505] (Step 3) Thereafter, phenylboronic acid (122.0 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.76 mg) were added to a reaction vessel, and the mixture was stirred at 80° C. for 3 hours.

[0506] (Step 4) After cooling the obtained reaction mixture, an aqueous solution of sodium diethyldithiacarbamate was added and stirred at 40°C for 1 hour. The obtained reaction solution was cooled, the aqueous layer was removed, and the obtained organic layer was washed twice with 3% by mass aqueous ammonia and twice with water. The obtained solution was dropped into methanol and stirred, and a precipitate was generated. The obtained precipitate was dissolved in toluene (106 mL), alumina (33 g) was added, and the mixture was stirred for 3 hours. The obtained suspension was purified by passing it through a silica gel column. The obtained solution was dropped into methanol and stirred, and a precipitate was generated. The obtained precipitate was filtered and dried to obtain 1.47 g of polymer compound P2 of Comparative Example 1. The Mn of polymer compound P2 was 5.3 × 10 4 and Mw is 2.8×10 5 It was.

[0507] Based on the theoretical value calculated from the amounts of the charged raw materials, polymer compound P2 is presumed to be a copolymer composed of structural units derived from compound S2 and structural units derived from compound S3 in a molar ratio of 50:50.

[0508] Example 2 <Synthesis of polymer compound P3> (Step 1) After creating an inert gas atmosphere in a reaction vessel, the above compound S1 (1.017 g), the above compound MC1 (0.129 g), the above compound S3 (1.033 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.01 mg) and toluene (35 mL) were added and heated to 80°C.

[0509] (Step 2) Then, a 16% by mass aqueous solution of tetraethylammonium hydroxide (17.3 g) was added dropwise to the reaction vessel and refluxed for 6 hours.

[0510] (Step 3) Thereafter, phenylboronic acid (70.4 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.01 mg) were added to a reaction vessel, and the mixture was stirred at 80° C. for 3 hours.

[0511] (Step 4) After cooling the obtained reaction mixture, an aqueous solution of sodium diethyldithiacarbamate was added and stirred at 40°C for 1 hour. The obtained reaction solution was cooled, the aqueous layer was removed, and the obtained organic layer was washed twice with 3% by mass aqueous ammonia and twice with water. The obtained solution was dropped into methanol and stirred, and a precipitate was generated. The obtained precipitate was dissolved in toluene (99 mL), alumina (61 g) was added, and the mixture was stirred for 3 hours. The obtained suspension was purified by passing it through a silica gel column. The obtained solution was dropped into methanol and stirred, and a precipitate was generated. The obtained precipitate was filtered and dried to obtain 1.16 g of polymer compound P3 of Example 2. The Mn of polymer compound P3 was 4.9 × 10 4 and Mw is 3.4×10 5 It was.

[0512] From the theoretical values ​​calculated from the amounts of the charged raw materials, polymer compound P3 is presumed to be a random copolymer (a copolymer having no terminal blocks or non-terminal blocks) composed of a structural unit derived from compound S1, a structural unit derived from compound MC1, and a structural unit derived from compound S3 in a molar ratio of 47:3:50.

[0513] Comparative Example 2 <Synthesis of polymer compound P4> (Step 1) After creating an inert gas atmosphere in a reaction vessel, the above compound S2 (0.712 g), the above compound MC1 (0.202 g), the above compound S3 (1.573 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.54 mg) and toluene (36 mL) were added and heated to 80°C.

[0514] (Step 2) Then, a 16% by mass aqueous solution of tetraethylammonium hydroxide (17.8 g) was added dropwise to the reaction vessel and refluxed for 6 hours.

[0515] (Step 3) Thereafter, phenylboronic acid (107.0 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.54 mg) were added to a reaction vessel, and the mixture was stirred at 80° C. for 3 hours.

[0516] (Step 4) After cooling the obtained reaction mixture, an aqueous solution of sodium diethyldithiacarbamate was added and stirred at 40°C for 1 hour. The obtained reaction solution was cooled, the aqueous layer was removed, and the obtained organic layer was washed twice with 3% by mass aqueous ammonia and twice with water. The obtained solution was dropped into methanol and stirred, and a precipitate was generated. The obtained precipitate was dissolved in toluene (102 mL), alumina (26 g) was added, and the mixture was stirred for 3 hours. The obtained suspension was purified by passing it through a silica gel column. The obtained solution was dropped into methanol and stirred, and a precipitate was generated. The obtained precipitate was filtered and dried to obtain 1.29 g of polymer compound P4 of Comparative Example 2. The Mn of polymer compound P4 was 5.3 × 10 4 and Mw is 2.9 × 10 5 It was.

[0517] From the theoretical values ​​calculated from the amounts of the charged raw materials, polymer compound P4 is presumed to be a random copolymer (a copolymer having no terminal blocks or non-terminal blocks) composed of a structural unit derived from compound S2, a structural unit derived from compound MC1, and a structural unit derived from compound S3 in a molar ratio of 47:3:50.

[0518] Example 3 <Synthesis of polymer compound P9> (Step 1) After creating an inert gas atmosphere in a reaction vessel, the above compound S16 (0.837 g), the above compound S17 (0.145 g), the above compound S18 (0.566 g), the above compound S1 (0.361 g), the above compound MC2 (0.129 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.84 mg) and toluene (33 mL) were added and heated to 80°C.

[0519] (Step 2) Then, a 16% by mass aqueous solution of tetraethylammonium hydroxide (16.4 g) was added dropwise to the reaction vessel and refluxed for 6 hours.

[0520] (Step 3) Thereafter, phenylboronic acid (57.9 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.84 mg) were added to a reaction vessel, and the mixture was stirred at 80° C. for 3 hours.

[0521] (Step 4) After cooling the reaction mixture, an aqueous solution of sodium diethyldithiacarbamate was added and stirred at 40°C for 1 hour. The reaction solution was cooled, the aqueous layer was removed, and the organic layer was washed twice with 3% by mass aqueous ammonia and twice with water. The solution was added dropwise to methanol and stirred to produce a precipitate. The precipitate was dissolved in toluene (93 mL), alumina (29 g) was added, and the mixture was stirred for 3 hours. The suspension was passed through a silica gel column for purification. The solution was added dropwise to methanol and stirred to produce a precipitate. The precipitate was collected by filtration and dried to obtain 1.38 g of polymer compound P9 of Example 3. The Mn of polymer compound P9 was 4.5×10 4 and Mw is 2.7×10 5 It was.

[0522] From the theoretical values ​​calculated from the amounts of the charged raw materials, polymer compound P9 is presumed to be a random copolymer (a copolymer having no terminal blocks or non-terminal blocks) composed of a structural unit derived from compound S16, a structural unit derived from compound S17, a structural unit derived from compound S18, a structural unit derived from compound S1, and a structural unit derived from compound MC2 in a molar ratio of 40:10:27:20:3.

[0523] Example 4 <Synthesis of polymer compound P10> (Step 1) After creating an inert gas atmosphere in a reaction vessel, the above compound S16 (0.756 g), the above compound S20 (0.095 g), the above compound S18 (0.506 g), the above compound S1 (0.323 g), the above compound MC2 (0.116 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.75 mg) and toluene (29 mL) were added and heated to 80°C.

[0524] (Step 2) Then, a 16% by mass aqueous solution of tetraethylammonium hydroxide (14.3 g) was added dropwise to the reaction vessel and refluxed for 6 hours.

[0525] (Step 3) Thereafter, phenylboronic acid (51.8 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.75 mg) were added to a reaction vessel, and the mixture was stirred at 80° C. for 3 hours.

[0526] (Step 4) After cooling the reaction mixture, an aqueous solution of sodium diethyldithiacarbamate was added and stirred at 40°C for 1 hour. The reaction solution was cooled, the aqueous layer was removed, and the organic layer was washed twice with 3% by mass aqueous ammonia and twice with water. The solution was added dropwise to methanol and stirred to produce a precipitate. The precipitate was dissolved in toluene (82 mL), alumina (25 g) was added, and the mixture was stirred for 3 hours. The suspension was passed through a silica gel column for purification. The solution was added dropwise to methanol and stirred to produce a precipitate. The precipitate was collected by filtration and dried to obtain 1.17 g of polymer compound P10 of Example 4. The Mn of polymer compound P10 was 4.5×10 4 and Mw is 3.4×10 5 It was.

[0527] From the theoretical values ​​calculated from the amounts of the charged raw materials, polymer compound P10 is presumed to be a random copolymer (a copolymer having no terminal blocks or non-terminal blocks) composed of a structural unit derived from compound S16, a structural unit derived from compound S20, a structural unit derived from compound S18, a structural unit derived from compound S1, and a structural unit derived from compound MC2 in a molar ratio of 40:10:27:20:3.

[0528] Example 5 <Synthesis of polymer compound P11> (Step 1) After creating an inert gas atmosphere in a reaction vessel, the above compound S5 (0.515 g), the above compound S21 (0.112 g), the above compound S15 (0.699 g), the above compound S1 (0.495 g), the above compound MC2 (0.177 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.15 mg) and toluene (29 mL) were added and heated to 80°C.

[0529] (Step 2) Then, a 16% by mass aqueous solution of tetraethylammonium hydroxide (14.6 g) was added dropwise to the reaction vessel and refluxed for 6 hours.

[0530] (Step 3) Thereafter, phenylboronic acid (79.3 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.15 mg) were added to a reaction vessel, and the mixture was stirred at 80° C. for 3 hours.

[0531] (Step 4) After cooling the obtained reaction mixture, an aqueous solution of sodium diethyldithiacarbamate was added and stirred at 40°C for 1 hour. The obtained reaction solution was cooled, the aqueous layer was removed, and the obtained organic layer was washed twice with 3% by mass aqueous ammonia and twice with water. The obtained solution was dropped into methanol and stirred, and a precipitate was generated. The obtained precipitate was dissolved in toluene (83 mL), alumina (26 g) was added, and the mixture was stirred for 3 hours. The obtained suspension was purified by passing it through a silica gel column. The obtained solution was dropped into methanol and stirred, and a precipitate was generated. The obtained precipitate was filtered and dried to obtain 1.24 g of polymer compound P11 of Example 5. The Mn of polymer compound P11 was 5.7 x 10 4 and Mw is 3.4×10 5 It was.

[0532] From the theoretical values ​​calculated from the amounts of the charged raw materials, polymer compound P11 is presumed to be a random copolymer (a copolymer having no terminal blocks or non-terminal blocks) composed of a structural unit derived from compound S5, a structural unit derived from compound S21, a structural unit derived from compound S15, a structural unit derived from compound S1, and a structural unit derived from compound MC2 in a molar ratio of 40:10:27:20:3.

[0533] Example 6 <Synthesis of polymer compound P12> (Step 1) After creating an inert gas atmosphere in a reaction vessel, the above compound S16 (0.760 g), the above compound S20 (0.095 g), the above compound S18 (0.693 g), the above compound S1 (0.162 g), the above compound MC2 (0.116 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.75 mg) and toluene (29 mL) were added and heated to 80°C.

[0534] (Step 2) Then, a 16% by mass aqueous solution of tetraethylammonium hydroxide (14.6 g) was added dropwise to the reaction vessel and refluxed for 6 hours.

[0535] (Step 3) Thereafter, phenylboronic acid (51.8 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.75 mg) were added to a reaction vessel, and the mixture was stirred at 80° C. for 3 hours.

[0536] (Step 4) After cooling the reaction mixture, an aqueous solution of sodium diethyldithiacarbamate was added and stirred at 40°C for 1 hour. The reaction solution was cooled, the aqueous layer was removed, and the organic layer was washed twice with 3% by mass aqueous ammonia and twice with water. The solution was added dropwise to methanol and stirred to produce a precipitate. The precipitate was dissolved in toluene (83 mL), alumina (26 g) was added, and the mixture was stirred for 3 hours. The suspension was passed through a silica gel column for purification. The solution was added dropwise to methanol and stirred to produce a precipitate. The precipitate was collected by filtration and dried to obtain 1.18 g of polymer compound P12 of Example 6. The Mn of polymer compound P12 was 5.0 x 10 4 and Mw is 3.0×10 5 It was.

[0537] From the theoretical values ​​calculated from the amounts of the charged raw materials, polymer compound P12 is presumed to be a random copolymer (a copolymer having no terminal blocks or non-terminal blocks) composed of a structural unit derived from compound S16, a structural unit derived from compound S20, a structural unit derived from compound S18, a structural unit derived from compound S1, and a structural unit derived from compound MC2 in a molar ratio of 40:10:37:10:3.

[0538] Example 7 <Synthesis of polymer compound P13> (Step 1) After creating an inert gas atmosphere in a reaction vessel, the above compound S16 (0.933 g), the above compound S20 (0.117 g), the above compound S18 (0.463 g), the above compound S1 (0.200 g), the above compound S22 (0.285 g), the above compound MC2 (0.143 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.93 mg) and toluene (34 mL) were added and heated to 80°C.

[0539] (Step 2) Then, a 16% by mass aqueous solution of tetraethylammonium hydroxide (16.9 g) was added dropwise to the reaction vessel and refluxed for 6 hours.

[0540] (Step 3) Thereafter, phenylboronic acid (64.0 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.93 mg) were added to a reaction vessel, and the mixture was stirred at 80° C. for 3 hours.

[0541] (Step 4) After cooling the obtained reaction mixture, an aqueous solution of sodium diethyldithiacarbamate was added and stirred at 40°C for 1 hour. The obtained reaction solution was cooled, the aqueous layer was removed, and the obtained organic layer was washed twice with 3% by mass aqueous ammonia and twice with water. The obtained solution was dropped into methanol and stirred, and a precipitate was generated. The obtained precipitate was dissolved in toluene (96 mL), alumina (60 g) was added, and the mixture was stirred for 3 hours. The obtained suspension was purified by passing it through a silica gel column. The obtained solution was dropped into methanol and stirred, and a precipitate was generated. The obtained precipitate was filtered and dried to obtain 1.05 g of polymer compound P13 of Example 7. The Mn of polymer compound P13 was 6.4 × 10 4 and Mw is 2.8×10 5 It was.

[0542] From the theoretical values ​​calculated from the amounts of the charged raw materials, polymer compound P13 is presumed to be a random copolymer (a copolymer having no terminal blocks or non-terminal blocks) composed of a structural unit derived from compound S16, a structural unit derived from compound S20, a structural unit derived from compound S18, a structural unit derived from compound S1, a structural unit derived from compound S22, and a structural unit derived from compound MC2 in a molar ratio of 40:10:20:10:17:3.

[0543] Example 8 <Synthesis of polymer compound P14> (Step 1) After creating an inert gas atmosphere in a reaction vessel, the above compound S16 (0.844 g), the above compound S17 (0.143 g), the above compound S18 (0.774 g), the above compound S1 (0.181 g), the above compound MC2 (0.129 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.84 mg) and toluene (33 mL) were added and heated to 80°C.

[0544] (Step 2) Then, a 16% by mass aqueous solution of tetraethylammonium hydroxide (16.7 g) was added dropwise to the reaction vessel and refluxed for 6 hours.

[0545] (Step 3) Thereafter, phenylboronic acid (57.9 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.84 mg) were added to a reaction vessel, and the mixture was stirred at 80° C. for 3 hours.

[0546] (Step 4) After cooling the reaction mixture, an aqueous solution of sodium diethyldithiacarbamate was added and stirred at 40°C for 1 hour. The reaction solution was cooled, the aqueous layer was removed, and the organic layer was washed twice with 3% by mass aqueous ammonia and twice with water. The solution was added dropwise to methanol and stirred to produce a precipitate. The precipitate was dissolved in toluene (95 mL), alumina (59 g) was added, and the mixture was stirred for 3 hours. The suspension was passed through a silica gel column for purification. The solution was added dropwise to methanol and stirred to produce a precipitate. The precipitate was collected by filtration and dried to obtain 1.21 g of polymer compound P14 of Example 8. The Mn of polymer compound P14 was 4.1 x 10 4 and Mw is 2.3×10 5 It was.

[0547] From the theoretical values ​​calculated from the amounts of the charged raw materials, polymer compound P14 is presumed to be a random copolymer (a copolymer having no terminal blocks or non-terminal blocks) composed of a structural unit derived from compound S16, a structural unit derived from compound S17, a structural unit derived from compound S18, a structural unit derived from compound S1, and a structural unit derived from compound MC2 in a molar ratio of 40:10:37:10:3.

[0548] Example 9 <Synthesis of polymer compound P15> (Step 1) After creating an inert gas atmosphere in a reaction vessel, the above compound S16 (0.931 g), the above compound S20 (0.117 g), the above compound S18 (0.404 g), the above compound S1 (0.250 g), the above compound S22 (0.285 g), the above compound MC2 (0.143 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.93 mg) and toluene (34 mL) were added and heated to 80°C.

[0549] (Step 2) Then, a 16% by mass aqueous solution of tetraethylammonium hydroxide (16.8 g) was added dropwise to the reaction vessel and refluxed for 6 hours.

[0550] (Step 3) Thereafter, phenylboronic acid (64.0 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.93 mg) were added to a reaction vessel, and the mixture was stirred at 80° C. for 3 hours.

[0551] (Step 4) After cooling the reaction mixture, an aqueous solution of sodium diethyldithiacarbamate was added and stirred at 40°C for 1 hour. The reaction solution was cooled, the aqueous layer was removed, and the organic layer was washed twice with 3% by mass aqueous ammonia and twice with water. The solution was added dropwise to methanol and stirred to produce a precipitate. The precipitate was dissolved in toluene (96 mL), alumina (60 g) was added, and the mixture was stirred for 3 hours. The suspension was passed through a silica gel column for purification. The solution was added dropwise to methanol and stirred to produce a precipitate. The precipitate was collected by filtration and dried to obtain 1.12 g of polymer compound P15 of Example 9. The Mn of polymer compound P15 was 8.0 x 10 4 and Mw is 3.0×10 5 It was.

[0552] From the theoretical values ​​calculated from the amounts of the charged raw materials, polymer compound P15 is presumed to be a random copolymer (a copolymer having no terminal blocks or non-terminal blocks) composed of a structural unit derived from compound S16, a structural unit derived from compound S20, a structural unit derived from compound S18, a structural unit derived from compound S1, a structural unit derived from compound S22, and a structural unit derived from compound MC2 in a molar ratio of 40:10:17.5:12.5:17:3.

[0553] Example 10 <Synthesis of polymer compound P16> (Step 1) After creating an inert gas atmosphere in a reaction vessel, the above compound S16 (0.930 g), the above compound S20 (0.117 g), the above compound S18 (0.347 g), the above compound S1 (0.300 g), the above compound S22 (0.285 g), the above compound MC2 (0.143 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.93 mg) and toluene (34 mL) were added and heated to 80°C.

[0554] (Step 2) Then, a 16% by mass aqueous solution of tetraethylammonium hydroxide (16.8 g) was added dropwise to the reaction vessel and refluxed for 6 hours.

[0555] (Step 3) Thereafter, phenylboronic acid (64.0 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.93 mg) were added to a reaction vessel, and the mixture was stirred at 80° C. for 3 hours.

[0556] (Step 4) After cooling the obtained reaction mixture, an aqueous solution of sodium diethyldithiacarbamate was added and stirred at 40°C for 1 hour. The obtained reaction solution was cooled, the aqueous layer was removed, and the obtained organic layer was washed twice with 3% by mass aqueous ammonia and twice with water. The obtained solution was dropped into methanol and stirred, and a precipitate was generated. The obtained precipitate was dissolved in toluene (95 mL), alumina (60 g) was added, and the mixture was stirred for 3 hours. The obtained suspension was purified by passing it through a silica gel column. The obtained solution was dropped into methanol and stirred, and a precipitate was generated. The obtained precipitate was filtered and dried to obtain 1.16 g of polymer compound P16 of Example 10. The Mn of polymer compound P16 was 7.8 x 10 4 and Mw is 3.1×10 5 It was.

[0557] From the theoretical values ​​calculated from the amounts of the charged raw materials, polymer compound P16 is presumed to be a random copolymer (a copolymer having no terminal blocks or non-terminal blocks) composed of a structural unit derived from compound S16, a structural unit derived from compound S20, a structural unit derived from compound S18, a structural unit derived from compound S1, a structural unit derived from compound S22, and a structural unit derived from compound MC2 in a molar ratio of 40:10:15:15:17:3.

[0558] Example 11 <Synthesis of polymer compound P17> (Step 1) After creating an inert gas atmosphere in a reaction vessel, the above compound S16 (0.931 g), the above compound S20 (0.117 g), the above compound S18 (0.463 g), the above compound S1 (0.199 g), the above compound S27 (0.291 g), the above compound MC2 (0.143 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.93 mg) and toluene (34 mL) were added and heated to 80°C.

[0559] (Step 2) Thereafter, a 16% by mass aqueous solution of tetraethylammonium hydroxide (17.0 g) was added dropwise to the reaction vessel, and the mixture was refluxed for 6 hours.

[0560] (Step 3) Thereafter, phenylboronic acid (64.0 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.93 mg) were added to a reaction vessel, and the mixture was stirred at 80° C. for 3 hours.

[0561] (Step 4) After cooling the reaction mixture, an aqueous solution of sodium diethyldithiacarbamate was added and stirred at 40°C for 1 hour. The reaction solution was cooled, the aqueous layer was removed, and the organic layer was washed twice with 3% by mass aqueous ammonia and twice with water. The solution was added dropwise to methanol and stirred to produce a precipitate. The precipitate was dissolved in toluene (97 mL), alumina (60 g) was added, and the mixture was stirred for 3 hours. The suspension was passed through a silica gel column for purification. The solution was added dropwise to methanol and stirred to produce a precipitate. The precipitate was collected by filtration and dried to obtain 1.09 g of polymer compound P17 of Example 11. The Mn of polymer compound P17 was 6.8 x 10 4 and Mw is 3.1×10 5 It was.

[0562] From the theoretical values ​​calculated from the amounts of the charged raw materials, polymer compound P17 is presumed to be a random copolymer (a copolymer having no terminal blocks or non-terminal blocks) composed of a structural unit derived from compound S16, a structural unit derived from compound S20, a structural unit derived from compound S18, a structural unit derived from compound S1, a structural unit derived from compound S27, and a structural unit derived from compound MC2 in a molar ratio of 40:10:20:10:17:3.

[0563] Example 12 <Synthesis of polymer compound P18> (Step 1) After creating an inert gas atmosphere in a reaction vessel, the above compound S16 (0.924 g), the above compound S17 (0.158 g), the above compound S18 (0.463 g), the above compound S1 (0.199 g), the above compound S22 (0.285 g), the above compound MC2 (0.143 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.93 mg) and toluene (35 mL) were added and heated to 80°C.

[0564] (Step 2) Then, a 16% by mass aqueous solution of tetraethylammonium hydroxide (17.3 g) was added dropwise to the reaction vessel and refluxed for 6 hours.

[0565] (Step 3) Thereafter, phenylboronic acid (64.0 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.93 mg) were added to a reaction vessel, and the mixture was stirred at 80° C. for 3 hours.

[0566] (Step 4) After cooling the obtained reaction mixture, an aqueous solution of sodium diethyldithiacarbamate was added and stirred at 40°C for 1 hour. The obtained reaction solution was cooled, the aqueous layer was removed, and the obtained organic layer was washed twice with 3% by mass aqueous ammonia and twice with water. The obtained solution was dropped into methanol and stirred, and a precipitate was generated. The obtained precipitate was dissolved in toluene (99 mL), alumina (62 g) was added, and the mixture was stirred for 3 hours. The obtained suspension was purified by passing it through a silica gel column. The obtained solution was dropped into methanol and stirred, and a precipitate was generated. The obtained precipitate was filtered and dried to obtain 1.11 g of polymer compound P18 of Example 12. The Mn of polymer compound P18 was 6.7 x 10 4 and Mw is 2.9 × 10 5 It was.

[0567] From the theoretical values ​​calculated from the amounts of the charged raw materials, polymer compound P18 is presumed to be a random copolymer (a copolymer having no terminal blocks or non-terminal blocks) composed of a structural unit derived from compound S16, a structural unit derived from compound S17, a structural unit derived from compound S18, a structural unit derived from compound S1, a structural unit derived from compound S22, and a structural unit derived from compound MC2 in a molar ratio of 40:10:20:10:17:3.

[0568] Example 13 <Synthesis of polymer compound P19> (Step 1) After creating an inert gas atmosphere in a reaction vessel, the above compound S16 (0.921 g), the above compound S20 (0.117 g), the above compound S1 (0.597 g), the above compound S22 (0.285 g), the above compound MC2 (0.143 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.93 mg) and toluene (32 mL) were added and heated to 80°C.

[0569] (Step 2) Then, a 16% by mass aqueous solution of tetraethylammonium hydroxide (16.2 g) was added dropwise to the reaction vessel and refluxed for 6 hours.

[0570] (Step 3) Thereafter, phenylboronic acid (64.0 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.93 mg) were added to a reaction vessel, and the mixture was stirred at 80° C. for 3 hours.

[0571] (Step 4) After cooling the reaction mixture, an aqueous solution of sodium diethyldithiacarbamate was added and stirred at 40°C for 1 hour. The reaction solution was cooled, the aqueous layer was removed, and the organic layer was washed twice with 3% by mass aqueous ammonia and twice with water. The solution was added dropwise to methanol and stirred to produce a precipitate. The precipitate was dissolved in toluene (92 mL), alumina (58 g) was added, and the mixture was stirred for 3 hours. The suspension was passed through a silica gel column for purification. The solution was added dropwise to methanol and stirred to produce a precipitate. The precipitate was collected by filtration and dried to obtain 1.09 g of polymer compound P19 of Example 13. The Mn of polymer compound P19 was 6.6 x 10 4 and Mw is 2.9 × 10 5 It was.

[0572] From the theoretical values ​​calculated from the amounts of the charged raw materials, polymer compound P19 is presumed to be a random copolymer (a copolymer having no terminal blocks or non-terminal blocks) composed of a structural unit derived from compound S16, a structural unit derived from compound S20, a structural unit derived from compound S1, a structural unit derived from compound S22, and a structural unit derived from compound MC2 in a molar ratio of 40:10:30:17:3.

[0573] Comparative Example 3 <Synthesis of polymer compound P20> (Step 1) After creating an inert gas atmosphere in a reaction vessel, the above compound S23 (0.742 g), the above compound S21 (0.121 g), the above compound S15 (0.753 g), the above compound S19 (0.258 g), the above compound MC2 (0.191 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.23 mg) and toluene (30 mL) were added and heated to 80°C.

[0574] (Step 2) Thereafter, a 16% by mass aqueous solution of tetraethylammonium hydroxide (15.0 g) was added dropwise to the reaction vessel, and the mixture was refluxed for 6 hours.

[0575] (Step 3) Thereafter, phenylboronic acid (85.4 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.23 mg) were added to a reaction vessel, and the mixture was stirred at 80° C. for 3 hours.

[0576] (Step 4) After cooling the reaction mixture, an aqueous solution of sodium diethyldithiacarbamate was added and stirred at 40°C for 1 hour. The reaction solution was cooled, the aqueous layer was removed, and the organic layer was washed twice with 3% by mass aqueous ammonia and twice with water. The solution was added dropwise to methanol and stirred to produce a precipitate. The precipitate was dissolved in toluene (85 mL), alumina (27 g) was added, and the mixture was stirred for 3 hours. The suspension was passed through a silica gel column for purification. The solution was added dropwise to methanol and stirred to produce a precipitate. The precipitate was collected by filtration and dried to obtain 1.12 g of polymer compound P20 of Comparative Example 3. The Mn of polymer compound P20 was 8.0 x 10 4 and Mw is 2.5×10 5 It was.

[0577] From the theoretical values ​​calculated from the amounts of the charged raw materials, polymer compound P20 is presumed to be a random copolymer (a copolymer having no terminal blocks or non-terminal blocks) composed of a structural unit derived from compound S23, a structural unit derived from compound S21, a structural unit derived from compound S15, a structural unit derived from compound S19, and a structural unit derived from compound MC2 in a molar ratio of 40:10:27:20:3.

[0578] Example 14 <Synthesis of polymer compound P21> (Step 1) After creating an inert gas atmosphere in a reaction vessel, the above compound S3 (1.123 g), the above compound S1 (0.588 g), the above compound S24 (0.270 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.10 mg) and toluene (30 mL) were added and heated to 80°C.

[0579] (Step 2) Then, a 16% by mass aqueous solution of tetraethylammonium hydroxide (14.9 g) was added dropwise to the reaction vessel and refluxed for 6 hours.

[0580] (Step 3) Thereafter, phenylboronic acid (76.2 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.10 mg) were added to a reaction vessel, and the mixture was stirred at 80° C. for 3 hours.

[0581] (Step 4) After cooling the reaction mixture, an aqueous solution of sodium diethyldithiacarbamate was added and stirred at 40°C for 1 hour. The reaction solution was cooled, the aqueous layer was removed, and the organic layer was washed twice with 3% by mass aqueous ammonia and twice with water. The solution was added dropwise to methanol and stirred to produce a precipitate. The precipitate was dissolved in toluene (85 mL), alumina (53 g) was added, and the mixture was stirred for 3 hours. The suspension was passed through a silica gel column for purification. The solution was added dropwise to methanol and stirred to produce a precipitate. The precipitate was collected by filtration and dried to obtain 0.98 g of polymer compound P21 of Example 14. The Mn of polymer compound P21 was 5.6 x 10 4 and Mw is 2.8×10 5 It was.

[0582] From the theoretical values ​​calculated from the amounts of the charged raw materials, polymer compound P21 is presumed to be a random copolymer (a copolymer having no terminal blocks or non-terminal blocks) composed of a structural unit derived from compound S3, a structural unit derived from compound S1, and a structural unit derived from compound S24 in a molar ratio of 50:25:25.

[0583] Example 15 <Synthesis of polymer compound P22> (Step 1) After the inside of a reaction vessel was filled with an inert gas atmosphere, the above compound S25 (0.984 g), the above compound S26 (0.119 g), the above compound S18 (0.793 g), the above compound S1 (0.452 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.06 mg) and toluene (37 mL) were added and heated to 80°C.

[0584] (Step 2) Then, a 16% by mass aqueous solution of tetraethylammonium hydroxide (18.8 g) was added dropwise to the reaction vessel and refluxed for 6 hours.

[0585] (Step 3) Thereafter, phenylboronic acid (73.2 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.06 mg) were added to a reaction vessel, and the mixture was stirred at 80° C. for 3 hours.

[0586] (Step 4) After cooling the reaction mixture, an aqueous solution of sodium diethyldithiacarbamate was added and stirred at 40°C for 1 hour. The reaction solution was cooled, the aqueous layer was removed, and the organic layer was washed twice with 3% by mass aqueous ammonia and twice with water. The solution was added dropwise to methanol and stirred to produce a precipitate. The precipitate was dissolved in toluene (107 mL), alumina (67 g) was added, and the mixture was stirred for 3 hours. The suspension was passed through a silica gel column for purification. The solution was added dropwise to methanol and stirred to produce a precipitate. The precipitate was collected by filtration and dried to obtain 1.22 g of polymer compound P22 of Example 15. The Mn of polymer compound P22 was 3.3 x 10 4 and Mw is 2.2 × 10 5 It was.

[0587] From the theoretical values ​​calculated from the amounts of the charged raw materials, polymer compound P22 is presumed to be a random copolymer (a copolymer having no terminal blocks or non-terminal blocks) composed of a structural unit derived from compound S25, a structural unit derived from compound S26, a structural unit derived from compound S18, and a structural unit derived from compound S1 in a molar ratio of 40:10:30:20.

[0588] Synthesis Example 1 <Synthesis of polymer compound P5> Polymer compound P5 was synthesized according to the method described in JP 2012-144722 A using mixture P5-1 (compounds S7, S8, S4, S6 and S9) shown in Table 2. The Mn of polymer compound P5 was 1.0 × 10 5and Mw is 2.9 × 10 5 It was.

[0589] [Table 2]

[0590] From the theoretical values ​​calculated from the amounts of the charged raw materials, polymer compound P5 is presumed to be a random copolymer (a copolymer having no terminal blocks or non-terminal blocks) composed of a structural unit derived from compound S7, a structural unit derived from compound S8, a structural unit derived from compound S4, a structural unit derived from compound S6, and a structural unit derived from compound S9 in a molar ratio of 50:32:10:3:5.

[0591] Synthesis Example 2 <Synthesis of polymer compound P6> Polymer compound P6 was synthesized according to the method described in JP 2012-144722 A using mixture P6-1 (compound S3 and compound S10) shown in Table 3. The Mn of polymer compound P6 was 6.9 × 10 4 and Mw is 2.1×10 5 It was.

[0592] [Table 3]

[0593] Based on the theoretical values ​​calculated from the amounts of the raw materials charged, polymer compound P6 is presumed to be a copolymer composed of structural units derived from compound S3 and structural units derived from compound S10 in a molar ratio of 50:50.

[0594] Synthesis Example 3 <Synthesis of polymer compound P7> Polymer compound P7 is a mixture P7-1a (compound S5 and compound S11) shown in Table 4. In addition, the mixture P7-1b (compound S5 and compound S12) was used to synthesize according to the method described in JP 2019-195057 A. The Mn of the polymer compound P7 was 4.4 × 10 4 and Mw is 1.1×10 5 It was.

[0595] [Table 4]

[0596] From the theoretical values ​​calculated from the amounts of the charged raw materials, polymer compound P7 is presumed to be a block copolymer having a non-terminal block composed of structural units derived from compound S5 and structural units derived from compound S11 in a molar ratio of 6.5:10, and a terminal block composed of structural units derived from compound S5 and structural units derived from compound S12 in a molar ratio of 43.5:40.

[0597] Synthesis Example 4 <Synthesis of polymer compound P8> Polymer compound P8 was synthesized according to the method described in JP 2015-086215 A using mixture P8-1 (compounds S13, S12, S14, S4 and S6) shown in Table 5. The Mn of polymer compound P8 was 1.4 × 10 5 and Mw is 4.1×10 5 It was.

[0598] [Table 5]

[0599] From the theoretical values ​​calculated from the amounts of the charged raw materials, polymer compound P8 is presumed to be a random copolymer (a copolymer having no terminal blocks or non-terminal blocks) composed of a structural unit derived from compound S13, a structural unit derived from compound S12, a structural unit derived from compound S14, a structural unit derived from compound S4, and a structural unit derived from compound S6 in a molar ratio of 50:10:5:30:5.

[0600] Example D1 <Fabrication of Light-emitting Device D1> (Formation of anode and hole injection layer) An ITO film was applied to a glass substrate by sputtering to a thickness of 45 nm to form an anode. A hole injection material ND-3202 manufactured by Nissan Chemical Industries was applied to a hole injection layer by spin coating to a thickness of 35 nm, and the material was heated on a hot plate at 50°C for 3 minutes in an air atmosphere to volatilize the solvent, and then heated on a hot plate at 240°C for 15 minutes to form a hole injection layer.

[0601] (Formation of Hole Transport Layer) Polymer compound P1 of Example 1 was dissolved in xylene at a concentration of 0.7% by 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 in a nitrogen gas atmosphere to form a hole transport layer.

[0602] (Formation of the light-emitting layer) The above-mentioned compound HM1, the above-mentioned compound COM-35, the above-mentioned compound COM-3 and the above-mentioned compound COM-7 (mass ratio: compound HM1 / compound COM-35 / compound COM-3 / compound COM-7=73.9 / 25 / 1 / 0.1) were dissolved in toluene as a solvent at a concentration of 2.0 mass % to prepare composition A. This composition A was used to form a film with a thickness of 75 nm on the hole transport layer by a spin coating method, and heated at 130° C. for 10 minutes in a nitrogen gas atmosphere to form a light emitting layer.

[0603] (Formation of Electron Transport Layer) The compound ETL1 was dissolved in 1H,1H,5H-octafluoropentanol at a concentration of 0.25% by mass to prepare a 1H,1H,5H-octafluoropentanol solution of the compound ETL1 at a concentration of 0.25% by mass. This solution was used to form a film with a thickness of 10 nm on the light-emitting layer by a spin coating method, and heated at 130° C. for 10 minutes in a nitrogen gas atmosphere to form an electron transport layer.

[0604] (Formation of cathode and electron injection layer) The substrate on which the electron transport layer was formed was placed in the deposition machine and evaporated at 1.0×10 -4 After reducing the pressure to below Pa, sodium fluoride was deposited to a thickness of about 4 nm on the electron transport layer as a cathode, and then aluminum was deposited to a thickness of about 100 nm on the electron transport layer. Thereafter, the light-emitting device D1 of Example D1 was produced by sealing the device with a glass substrate.

[0605] (Driving voltage measurement of light emitting element) For the light-emitting element D1 of Example D1, 1000 cd / m 2 The driving voltage during light emission was measured at 1000 V. The results are shown in Table 6.

[0606] (Evaluation of light-emitting elements) By applying a voltage to the light-emitting element D1, EL emission having a maximum peak wavelength of the emission spectrum at 515 nm was observed. The initial luminance was 6000 cd / m 2 After setting the current value so that the device was driven at a constant current, the change in luminance over time was measured. The time required for the luminance to reach 70% of the initial luminance (hereinafter also referred to as "LT70") was 121.6 hours.

[0607] Comparative Example CD1 <Fabrication of light-emitting element CD1> A light-emitting device CD1 of Comparative Example CD1 was produced and its driving voltage was measured in the same manner as in Example D1, except that the polymer compound P2 of Comparative Example 1 was used instead of the polymer compound P1 of Example 1. The results are shown in Table 6.

[0608] (Evaluation of light-emitting elements) By applying a voltage to the light-emitting element CD1, EL emission was observed with a maximum peak wavelength of the emission spectrum at 515 nm. The initial luminance was 6000 cd / m 2 After setting the current value so that the device was driven at a constant current, the change in luminance over time was measured. It took 35.4 hours for the luminance to reach 70% of the initial luminance.

[0609] Example D2 <Fabrication of Light-Emitting Element D2> Compound HM1, compound COM-35 and compound COM-3 (mass ratio: compound HM1 / compound COM-35 / compound COM-3=74 / 25 / 1) were dissolved in toluene as a solvent at a concentration of 2.0 mass% to prepare composition B. The light-emitting element D2 of Example D2 was produced in the same manner as in Example D1, except that the polymer compound P3 of Example 2 was used instead of the polymer compound P1 of Example 1 in forming the hole transport layer, and the composition B was used instead of the composition A in forming the light-emitting layer, and the driving voltage was measured. The results are shown in Table 6.

[0610] (Evaluation of light-emitting elements) By applying a voltage to the light-emitting element D2, EL emission having a maximum peak wavelength of the emission spectrum at 605 nm was observed. The initial luminance was 6000 cd / m 2 After setting the current value so that the device was driven at a constant current, the change in luminance over time was measured. It took 78.5 hours for the luminance to reach 70% of the initial luminance.

[0611] Comparative Example CD2 <Fabrication of light-emitting element CD2> A light-emitting device CD2 of Comparative Example CD2 was produced and its driving voltage was measured in the same manner as in Example D2, except that the polymer compound P4 of Comparative Example 2 was used instead of the polymer compound P3 of Example 2. The results are shown in Table 6.

[0612] (Evaluation of light-emitting elements) By applying a voltage to the light-emitting element CD2, EL emission was observed with a maximum peak wavelength of the emission spectrum at 605 nm. The initial luminance was 6000 cd / m 2 After setting the current value so that the device was driven at a constant current, the change in luminance over time was measured. It took 13.5 hours for the luminance to reach 70% of the initial luminance.

[0613] [Table 6]

[0614] Example D3 <Fabrication of light-emitting element D3> (Formation of anode and hole injection layer) An ITO film was applied to a glass substrate by sputtering to a thickness of 45 nm to form an anode. A hole injection material ND-3202 manufactured by Nissan Chemical Industries was applied to the anode by spin coating to a thickness of 35 nm, and the material was heated on a hot plate at 50°C for 3 minutes in an air atmosphere to volatilize the solvent, and then heated on a hot plate at 240°C for 15 minutes to form a hole injection layer.

[0615] (Formation of Hole Transport Layer) Polymer compound P1 of Example 1 was dissolved in xylene at a concentration of 0.7% by 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 in a nitrogen gas atmosphere to form a hole transport layer.

[0616] (Formation of the light-emitting layer) Polymer compound P5 and polymer compound P6 (mass ratio: polymer compound P5 / polymer compound P6=80 / 20) were dissolved in xylene as a solvent at a concentration of 1.2 mass % to prepare composition C. Composition C was used to form a film with a thickness of 60 nm on the hole transport layer by spin coating, and heated at 150° C. for 10 minutes in a nitrogen gas atmosphere to form a light emitting layer.

[0617] (Formation of cathode and electron injection layer) The substrate on which the light-emitting layer was formed was placed in the deposition machine and 1.0×10 -4 After reducing the pressure to below Pa, sodium fluoride was deposited to a thickness of about 4 nm on the electron transport layer as a cathode, and then aluminum was deposited thereon to a thickness of about 100 nm. Thereafter, the device was sealed using a glass substrate to prepare a light-emitting device D3 of Example D3.

[0618] (Driving voltage measurement of light emitting element) For the light-emitting element D3 of Example D3, 1000 cd / m 2 The driving voltage during light emission was measured at 1000 V. The results are shown in Table 7.

[0619] (Evaluation of light-emitting elements) By applying a voltage to the light-emitting element D3, EL emission having a maximum peak wavelength of the emission spectrum at 460 nm was observed. The initial luminance was 5000 cd / m 2 After setting the current value so that the device was driven at a constant current, the change in luminance over time was measured. It took 1.9 hours for the luminance to reach 70% of the initial luminance.

[0620] Example D17 <Fabrication of Light-emitting Device D17> A light-emitting device D17 of Example D17 was produced and its driving voltage was measured in the same manner as in Example D3, except that the polymer compound P21 was used instead of the polymer compound P1 of Example 1. The results are shown in Table 7.

[0621] (Evaluation of light-emitting elements) By applying a voltage to the light-emitting element D17, EL emission having a maximum peak wavelength of the emission spectrum at 460 nm was observed. The initial luminance was 5000 cd / m 2 After setting the current value so that the device was driven at a constant current, the change in luminance over time was measured. It took 2.7 hours for the luminance to reach 70% of the initial luminance.

[0622] Example D18 <Fabrication of light-emitting element D18> A light-emitting device D18 of Example D18 was produced and its driving voltage was measured in the same manner as in Example D3, except that the polymer compound P22 was used instead of the polymer compound P1 of Example 1. The results are shown in Table 7.

[0623] (Evaluation of light-emitting elements) By applying a voltage to the light-emitting element D18, EL emission having a maximum peak wavelength of the emission spectrum at 460 nm was observed. The initial luminance was 5000 cd / m 2 After setting the current value so that the device was driven at a constant current, the change in luminance over time was measured. It took 2.4 hours for the luminance to reach 70% of the initial luminance.

[0624] Comparative Example CD3 <Fabrication of light-emitting element CD3> A light-emitting device CD3 of Comparative Example CD3 was produced and its driving voltage was measured in the same manner as in Example D3, except that the polymer compound P2 of Comparative Example 1 was used instead of the polymer compound P1 of Example 1. The results are shown in Table 7.

[0625] (Evaluation of light-emitting elements) By applying a voltage to the light-emitting element CD3, EL emission was observed with a maximum peak wavelength of the emission spectrum at 460 nm. The initial luminance was 5000 cd / m 2 After setting the current value so that the device was driven at a constant current, the change in luminance over time was measured. It took 0.86 hours for the luminance to reach 70% of the initial luminance.

[0626] [Table 7]

[0627] Example D4 <Fabrication of Light-emitting Device D4> (Formation of anode and hole injection layer) An ITO film was applied to a glass substrate by sputtering to a thickness of 45 nm to form an anode. A hole injection material ND-3202 manufactured by Nissan Chemical Industries was applied to a hole injection layer by spin coating to a thickness of 65 nm, and the material was heated on a hot plate at 50°C for 3 minutes in an air atmosphere to volatilize the solvent, and then heated on a hot plate at 240°C for 15 minutes to form a hole injection layer.

[0628] (Formation of Hole Transport Layer) Polymer compound P1 of Example 1 was dissolved in xylene at a concentration of 0.7% by 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 in a nitrogen gas atmosphere to form a hole transport layer.

[0629] (Formation of the light-emitting layer) Polymer compound P7 and compound COM-3 (mass ratio: polymer compound P7 / compound COM-3=70 / 30) were dissolved in xylene as a solvent at a concentration of 2.2 mass % to prepare composition D. Composition D was used to form a film with a thickness of 85 nm on the hole transport layer by a spin coating method, and heated at 150° C. for 10 minutes in a nitrogen gas atmosphere to form a light emitting layer.

[0630] (Formation of cathode and electron injection layer) The substrate on which the light-emitting layer was formed was placed in the deposition machine and 1.0×10 -4 After reducing the pressure to below Pa, sodium fluoride was deposited to a thickness of about 4 nm on the electron transport layer as a cathode, and then aluminum was deposited thereon to a thickness of about 100 nm. Thereafter, the device was sealed using a glass substrate to prepare a light-emitting device D4 of Example D4.

[0631] (Driving voltage measurement of light emitting element) For the light-emitting element D4 of Example D4, 1000 cd / m 2 The driving voltage during light emission was measured at 1000 V. The results are shown in Table 8.

[0632] (Evaluation of light-emitting elements) By applying a voltage to the light-emitting element D4, EL emission having a maximum peak wavelength of the emission spectrum at 520 nm was observed. The initial luminance was 24,000 cd / m 2 After setting the current value so that the device was driven at a constant current, the change in luminance over time was measured. It took 14.8 hours for the luminance to reach 70% of the initial luminance.

[0633] Example D19 <Fabrication of Light-emitting Device D19> A light-emitting device D19 of Example D19 was produced and its driving voltage was measured in the same manner as in Example D4, except that the polymer compound P21 was used instead of the polymer compound P1 of Example 1. The results are shown in Table 8.

[0634] (Evaluation of light-emitting elements) By applying a voltage to the light-emitting element D19, EL emission having a maximum peak wavelength of the emission spectrum at 520 nm was observed. The initial luminance was 24,000 cd / m 2 After setting the current value so that the device was driven at a constant current, the change in luminance over time was measured. It took 15.9 hours for the luminance to reach 70% of the initial luminance.

[0635] Example D20 <Fabrication of Light-Emitting Element D20> A light-emitting device D20 of Example D20 was produced and its driving voltage was measured in the same manner as in Example D4, except that the polymer compound P22 was used instead of the polymer compound P1 of Example 1. The results are shown in Table 8.

[0636] (Evaluation of light-emitting elements) By applying a voltage to the light-emitting element D20, EL emission having a maximum peak wavelength of the emission spectrum at 520 nm was observed. The initial luminance was 24,000 cd / m 2 After setting the current value so that the device was driven at a constant current, the change in luminance over time was measured. It took 19.1 hours for the luminance to reach 70% of the initial luminance.

[0637] Comparative Example CD4 <Fabrication of light-emitting element CD4> A light-emitting device CD4 of Comparative Example CD4 was produced and its driving voltage was measured in the same manner as in Example D4, except that the polymer compound P2 of Comparative Example 1 was used instead of the polymer compound P1 of Example 1. The results are shown in Table 8.

[0638] (Evaluation of light-emitting elements) By applying a voltage to the light-emitting element CD4, EL emission was observed with a maximum peak wavelength of the emission spectrum at 520 nm. The initial luminance was 24,000 cd / m 2 After setting the current value so that the device was driven at a constant current, the change in luminance over time was measured. It took 5.8 hours for the luminance to reach 70% of the initial luminance.

[0639] [Table 8]

[0640] Example D5 <Fabrication of light-emitting element D5> (Formation of anode and hole injection layer) An ITO film was applied to a glass substrate by sputtering to a thickness of 45 nm to form an anode. A hole injection material ND-3202 manufactured by Nissan Chemical Industries was applied to a hole injection layer by spin coating to a thickness of 65 nm, and the material was heated on a hot plate at 50°C for 3 minutes in an air atmosphere to volatilize the solvent, and then heated on a hot plate at 240°C for 15 minutes to form a hole injection layer.

[0641] (Formation of Hole Transport Layer) Polymer compound P1 of Example 1 was dissolved in xylene at a concentration of 0.7% by 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 in a nitrogen gas atmosphere to form a hole transport layer.

[0642] (Formation of the light-emitting layer) Polymer compound P8 and compound COM-7 (mass ratio: polymer compound P8 / compound COM-7=92.5 / 7.5) were dissolved in xylene as a solvent at a concentration of 2.0 mass % to prepare composition E. Composition E was used to form a film with a thickness of 85 nm on the hole transport layer by spin coating, and heated at 150° C. for 10 minutes in a nitrogen gas atmosphere to form a light emitting layer.

[0643] (Formation of cathode and electron injection layer) The substrate on which the light-emitting layer was formed was placed in the deposition machine and 1.0×10 -4 After reducing the pressure to below Pa, sodium fluoride was deposited to a thickness of about 4 nm on the electron transport layer as a cathode, and then aluminum was deposited thereon to a thickness of about 100 nm. Thereafter, the device was sealed using a glass substrate to prepare a light-emitting device D5 of Example D5.

[0644] (Driving voltage measurement of light emitting element) For the light-emitting element D5 of Example D5, 1000 cd / m 2 The driving voltage during light emission was measured at 1000 V. The results are shown in Table 9.

[0645] (Evaluation of light-emitting elements) By applying a voltage to the light-emitting element D5, EL emission having a maximum peak wavelength of the emission spectrum at 615 nm was observed. The initial luminance was 12000 cd / m 2 After setting the current value so that the device was driven at a constant current, the change in luminance over time was measured. It took 126.1 hours for the luminance to reach 70% of the initial luminance.

[0646] Example D21 <Fabrication of Light-emitting Device D21> A light-emitting device D21 of Example D21 was produced and its driving voltage was measured in the same manner as in Example D5, except that the polymer compound P21 was used instead of the polymer compound P1 of Example 1. The results are shown in Table 9.

[0647] (Evaluation of light-emitting elements) By applying a voltage to the light-emitting element D21, EL emission having a maximum peak wavelength of the emission spectrum at 615 nm was observed. The initial luminance was 12000 cd / m 2 After setting the current value so that the device was driven at a constant current, the change in luminance over time was measured. It took 137.1 hours for the luminance to reach 70% of the initial luminance.

[0648] Example D22 <Fabrication of Light-Emitting Element D22> A light-emitting device D22 of Example D22 was produced and its driving voltage was measured in the same manner as in Example D5, except that the polymer compound P22 was used instead of the polymer compound P1 of Example 1. The results are shown in Table 9.

[0649] (Evaluation of light-emitting elements) By applying a voltage to the light-emitting element D22, EL emission having a maximum peak wavelength of the emission spectrum at 615 nm was observed. The initial luminance was 12000 cd / m 2After setting the current value so that the device was driven at a constant current, the change in luminance over time was measured. It took 161.2 hours for the luminance to reach 70% of the initial luminance.

[0650] Comparative Example CD5 <Fabrication of light-emitting element CD5> A light-emitting device CD5 of Comparative Example CD5 was produced and its driving voltage was measured in the same manner as in Example D5, except that the polymer compound P2 of Comparative Example 1 was used instead of the polymer compound P1 of Example 1. The results are shown in Table 9.

[0651] (Evaluation of light-emitting elements) By applying a voltage to the light-emitting element CD5, EL emission was observed with a maximum peak wavelength of the emission spectrum at 615 nm. The initial luminance was 12000 cd / m 2 After setting the current value so that the device was driven at a constant current, the change in luminance over time was measured. It took 41.4 hours for the luminance to reach 70% of the initial luminance.

[0652] [Table 9]

[0653] <Fabrication of Light-emitting Device D6> A light-emitting device D6 of Example D6 was produced and its driving voltage was measured in the same manner as in Example D2, except that polymer compound P9 was used instead of polymer compound P3 of Example 2. The results are shown in Table 10.

[0654] (Evaluation of light-emitting elements) By applying a voltage to the light-emitting element D6, EL emission having a maximum peak wavelength of the emission spectrum at 510 nm was observed. The initial luminance was 6000 cd / m 2 After setting the current value so that the device was driven at a constant current, the change in luminance over time was measured. It took 76.3 hours for the luminance to reach 50% of the initial luminance.

[0655] <Fabrication of Light-emitting Device D7> A light-emitting device D7 of Example D7 was produced and its driving voltage was measured in the same manner as in Example D2, except that polymer compound P10 was used instead of polymer compound P3 of Example 2. The results are shown in Table 10.

[0656] (Evaluation of light-emitting elements) By applying a voltage to the light-emitting element D7, EL emission having a maximum peak wavelength of the emission spectrum at 510 nm was observed. The initial luminance was 6000 cd / m 2 After setting the current value so that the device was driven at a constant current, the change in luminance over time was measured. It took 79.8 hours for the luminance to reach 50% of the initial luminance.

[0657] <Fabrication of Light-emitting Device D8> A light-emitting device D8 of Example D8 was produced in the same manner as in Example D2, except that polymer compound P11 was used instead of polymer compound P3 of Example 2, and the driving voltage was measured. The results are shown in Table 10.

[0658] (Evaluation of light-emitting elements) By applying a voltage to the light-emitting element D8, EL emission having a maximum peak wavelength of the emission spectrum at 510 nm was observed. The initial luminance was 6000 cd / m 2 After setting the current value so that the device was driven at a constant current, the change in luminance over time was measured. It took 78.1 hours for the luminance to reach 50% of the initial luminance.

[0659] <Fabrication of Light-emitting Device D9> A light-emitting device D9 of Example D9 was produced and its driving voltage was measured in the same manner as in Example D2, except that the polymer compound P12 was used instead of the polymer compound P3 of Example 2. The results are shown in Table 10.

[0660] (Evaluation of light-emitting elements) By applying a voltage to the light-emitting element D9, EL emission having a maximum peak wavelength of the emission spectrum at 510 nm was observed. The initial luminance was 6000 cd / m 2After setting the current value so that the device was driven at a constant current, the change in luminance over time was measured. It took 84.6 hours for the luminance to reach 50% of the initial luminance.

[0661] <Fabrication of Light-emitting Device D10> A light-emitting device D10 of Example D10 was produced and its driving voltage was measured in the same manner as in Example D2, except that the polymer compound P13 was used instead of the polymer compound P3 of Example 2. The results are shown in Table 10.

[0662] (Evaluation of light-emitting elements) By applying a voltage to the light-emitting element D10, EL emission having a maximum peak wavelength of the emission spectrum at 510 nm was observed. The initial luminance was 6000 cd / m 2 After setting the current value so that the device was driven at a constant current, the change in luminance over time was measured. It took 94.0 hours for the luminance to reach 50% of the initial luminance.

[0663] <Fabrication of Light-emitting Device D11> A light-emitting device D11 of Example D11 was produced and its driving voltage was measured in the same manner as in Example D2, except that the polymer compound P14 was used instead of the polymer compound P3 of Example 2. The results are shown in Table 10.

[0664] (Evaluation of light-emitting elements) By applying a voltage to the light-emitting element D11, EL emission having a maximum peak wavelength of the emission spectrum at 510 nm was observed. The initial luminance was 6000 cd / m 2 After setting the current value so that the device was driven at a constant current, the change in luminance over time was measured. It took 85.3 hours for the luminance to reach 50% of the initial luminance.

[0665] <Fabrication of Light-Emitting Element D12> A light-emitting device D12 of Example D12 was produced and its driving voltage was measured in the same manner as in Example D2, except that the polymer compound P15 was used instead of the polymer compound P3 of Example 2. The results are shown in Table 10.

[0666] (Evaluation of light-emitting elements) By applying a voltage to the light-emitting element D12, EL emission having a maximum peak wavelength of the emission spectrum at 510 nm was observed. The initial luminance was 6000 cd / m 2 After setting the current value so that the device was driven at a constant current, the change in luminance over time was measured. It took 85.1 hours for the luminance to reach 50% of the initial luminance.

[0667] <Fabrication of Light-emitting Device D13> A light-emitting device D13 of Example D13 was produced and its driving voltage was measured in the same manner as in Example D2, except that polymer compound P16 was used instead of polymer compound P3 of Example 2. The results are shown in Table 10.

[0668] (Evaluation of light-emitting elements) By applying a voltage to the light-emitting element D13, EL emission having a maximum peak wavelength of the emission spectrum at 510 nm was observed. The initial luminance was 6000 cd / m 2 After setting the current value so that the device was driven at a constant current, the change in luminance over time was measured. It took 79.6 hours for the luminance to reach 50% of the initial luminance.

[0669] <Fabrication of Light-emitting Device D14> A light-emitting device D14 of Example D14 was produced and its driving voltage was measured in the same manner as in Example D2, except that polymer compound P17 was used instead of polymer compound P3 of Example 2. The results are shown in Table 10.

[0670] (Evaluation of light-emitting elements) By applying a voltage to the light-emitting element D14, EL emission having a maximum peak wavelength of the emission spectrum at 510 nm was observed. The initial luminance was 6000 cd / m 2 After setting the current value so that the device was driven at a constant current, the change in luminance over time was measured. It took 107.1 hours for the luminance to reach 50% of the initial luminance.

[0671] <Fabrication of light-emitting element D15> A light-emitting device D15 of Example D15 was produced and its driving voltage was measured in the same manner as in Example D2, except that polymer compound P18 was used instead of polymer compound P3 of Example 2. The results are shown in Table 10.

[0672] (Evaluation of light-emitting elements) By applying a voltage to the light-emitting element D15, EL emission having a maximum peak wavelength of the emission spectrum at 510 nm was observed. The initial luminance was 6000 cd / m 2 After setting the current value so that the device was driven at a constant current, the change in luminance over time was measured. It took 84.8 hours for the luminance to reach 50% of the initial luminance.

[0673] <Fabrication of Light-emitting Device D16> A light-emitting device D16 of Example D16 was produced and its driving voltage was measured in the same manner as in Example D2, except that polymer compound P19 was used instead of polymer compound P3 of Example 2. The results are shown in Table 10.

[0674] (Evaluation of light-emitting elements) By applying a voltage to the light-emitting element D16, EL emission having a maximum peak wavelength of the emission spectrum at 510 nm was observed. The initial luminance was 6000 cd / m 2 After setting the current value so that the device was driven at a constant current, the change in luminance over time was measured. It took 84.1 hours for the luminance to reach 50% of the initial luminance.

[0675] <Fabrication of light-emitting element CD6> A light-emitting device CD6 of Comparative Example CD6 was produced and its driving voltage was measured in the same manner as in Example D2, except that the polymer compound P20 was used instead of the polymer compound P3 in Example 2. The results are shown in Table 10.

[0676] (Evaluation of light-emitting elements) By applying a voltage to the light-emitting element CD6, EL emission was observed with a maximum peak wavelength of the emission spectrum at 615 nm. The initial luminance was 6000 cd / m 2After setting the current value so that the device was driven at a constant current, the change in luminance over time was measured. It took 1.3 hours for the luminance to reach 50% of the initial luminance.

[0677] [Table 10]

[0678] As shown in Tables 6 to 9, the light-emitting devices of Examples D1 to D5, which have an organic layer containing a crosslinked product of either the polymer compound P1 or P3 of the examples, had superior luminance life compared to the light-emitting devices of Comparative Examples CD1 to CD5, which have an organic layer containing a crosslinked product of the comparative polymer compound corresponding to the polymer compound P1 or P3.

[0679] As shown in Tables 7 to 9, the light-emitting devices of Examples D17 to D22, which have an organic layer containing a crosslinked product of either the polymer compound P21 or P22 of the examples, had superior luminance life compared to the light-emitting devices of Comparative Examples CD3 to CD5, which have an organic layer containing a crosslinked product of the comparative polymer compound corresponding to the polymer compound P21 or P22.

[0680] As shown in Table 10, the light-emitting devices of Examples D6 to D16, which have an organic layer containing a crosslinked product of any of the polymer compounds P9 to P19 of the examples, had superior luminance life compared to the light-emitting device of Comparison Example CD6, which has an organic layer containing a crosslinked product of the comparative polymer compound corresponding to the polymer compounds P9 to P19.

[0681] From the above results, it was confirmed that the polymer compound of the present invention is useful for producing a light-emitting device having excellent luminance life.

Claims

1. A polymer compound comprising a structural unit represented by formula (1). 【Chemistry 1】 [In the formula, n represents 0 or 1. R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ and R ８ 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, or a halogen atom, and these groups may have a substituent. Ar １ , Ar ２ , Ar ３ and Ar ４ each independently represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. Ar １ and Ar ２ may be bonded to each other to form a ring together with the nitrogen atom to which they are bonded. ３ and Ar ４ may be bonded to each other to form a ring together with the nitrogen atom to which they are bonded. R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ６ and R ７ , R ６ and R ８ , R １ and R ７ , R １ and R ８ , and R ７ and R ８ may be bonded to each other to form a ring together with the carbon atom to which they are bonded. XL １ represents a group represented by formula (X-1). XL ２ represents a hydrogen atom or a group represented by formula (X-1). 【Chemistry 2】 [In the formula, * indicates the bond position. n １Ｘ represents an integer of 0 or more and 5 or less. L １Ｘ represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, -NR １Ｘ R represents a group represented by the formula (I), an oxygen atom, or a sulfur atom, and these groups may have a substituent. １Ｘ L′ 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. １Ｘ When multiple are present, they may be the same or different. X １ represents a crosslinking group represented by formula (XL-1). 【Chemistry 3】 [In the formula, *1 represents a bonding position.]

2. The n １Ｘ The polymer compound according to claim 1 , wherein is 0.

3. The polymer compound according to claim 1 or 2, further comprising a constitutional unit represented by formula (Y): 【Chemistry 4】 [In the formula, 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 to each other, and these groups may have a substituent.

4. 4. The polymer compound according to claim 3, wherein the constitutional unit represented by formula (Y) is a constitutional unit represented by formula (Y-1) or formula (Y-2). 【Chemistry 5】 [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 may be the same or different, and adjacent R Ｙ１ may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. 【Chemistry 6】 [In the formula, R Ｙ１ has the same meaning as above. X Ｙ１ is -C(R Ｙ２ ) ２ -, -C(R Ｙ２ ) = C(R Ｙ２ )-or-C(R Ｙ２ ) ２ -C(R Ｙ２ ) ２ R represents a group represented by -. 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 may be the same or different, R Ｙ２ may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.

5. The polymer compound according to any one of claims 1 to 4, further comprising a structural unit having a group in which one or more hydrogen atoms have been removed from the metal complex represented by formula (2). 【Chemistry 7】 [In the formula, M represents a rhodium atom, a palladium atom, an iridium atom, or a platinum atom. n １ represents an integer of 1 or more, n ２ represents an integer of 0 or more, provided that when M is a rhodium atom or an iridium atom, n １ +n ２ is 3, and when M is a palladium atom or a platinum atom, n １ +n ２ is 2. E １ and E ２ each independently represents a carbon atom or a nitrogen atom. １ and E ２ At least one of E is a carbon atom. １ and E ２ When multiple are present, they may be the same or different. Ring L １ represents an aromatic heterocycle, and this aromatic heterocycle may have a substituent. When a plurality of such substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded. Ring L １ When multiple are present, they may be the same or different. Ring L ２ represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings may have a substituent. When a plurality of such substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded. Ring L ２ When multiple are present, they may be the same or different. Ring L １ and a substituent that may be present on ring L ２ may be bonded to each other to form a ring together with the atom to which they are bonded. A １ -G １ -A ２ represents an anionic bidentate ligand. １ and A ２ each independently represents a carbon atom, an oxygen atom, or a nitrogen atom, and these atoms may be atoms constituting a ring. １ is a single bond, or A １ and A ２ represents an atomic group constituting a bidentate ligand together with A. １ -G １ -A ２ When multiple are present, they may be the same or different.

6. The polymer compound according to claim 5, wherein the structural unit having a group obtained by removing one or more hydrogen atoms from the metal complex represented by formula (2) is a structural unit represented by formula (1-1B), formula (1-2B), formula (1-3B), or formula (1-4B). 【Chemistry 8】 [In the formula, M １Ｂ represents a group in which one hydrogen atom has been removed from the metal complex represented by the formula (2). L Ｃ is an oxygen atom, a sulfur atom, -N(R Ａ ) -, -C(R Ｂ ) ２ -, -C(R Ｂ ) = C(R Ｂ )-, -C≡C-, an arylene group or a divalent heterocyclic group, and these groups may have a substituent. Ａ 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. Ｂ 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. Ｂ may be the same or different and may be bonded to each other to form a ring together with the carbon atom to which they are bonded. Ｃ When multiple are present, they may be the same or different. n ｃ１ represents an integer of 0 or more. 【Chemistry 9】 [In the formula, M １Ｂ has the same meaning as above. L ｄ and L ｅ each independently represents an oxygen atom, a sulfur atom, or -N(R Ａ ) -, -C(R Ｂ ) ２ -, -C(R Ｂ ) = C(R Ｂ )-, -C≡C-, an arylene group or a divalent heterocyclic group, and these groups may have a substituent. Ａ and R Ｂ has the same meaning as above. ｄ and L ｅ When multiple are present, they may be the same or different. n ｄ１ and n ｅ１ Each independently represents an integer of 0 or more. ｄ１ may be the same or different. Ar １Ｍ represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent. 【Chemistry 10】 [In the formula, L ｄ and n ｄ１ has the same meaning as above. M ２Ｂ represents a group in which two hydrogen atoms have been removed from the metal complex represented by formula (2). 【Chemistry 11】 [In the formula, L ｄ and n ｄ１ has the same meaning as above. M ３Ｂ represents a group in which three hydrogen atoms have been removed from the metal complex represented by formula (2).

7. 7. The polymer compound according to claim 5, wherein the metal complex represented by formula (2) is a metal complex represented by formula (1-A). 【Chemistry 12】 [In the formula, M, n １ , n ２ , E １ and A １ -G １ -A ２ has the same meaning as above. Ring L １Ａ represents a pyridine ring, a diazabenzene ring, an azanaphthalene ring, a diazanaphthalene ring, a triazole ring or a diazole ring, and these rings may have a substituent. When a plurality of such substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded. Ring L １Ａ When multiple are present, they may be the same or different. E ２１Ａ , E ２２Ａ , E ２３Ａ and E ２４Ａ Each independently represents a nitrogen atom or a carbon atom. ２１Ａ , E ２２Ａ , E ２３Ａ and E ２４Ａ When multiple are present, they may be the same or different. ２１Ａ When is a nitrogen atom, R ２１Ａ does not exist. ２２Ａ When is a nitrogen atom, R ２２Ａ does not exist. ２３Ａ When is a nitrogen atom, R ２３Ａ does not exist. ２４Ａ When is a nitrogen atom, R ２４Ａ does not exist. R ２１Ａ , R ２２Ａ , R ２３Ａ and R ２４Ａ R 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, or a halogen atom, and these groups may have a substituent. ２１Ａ , R ２２Ａ , R ２３Ａ and R ２４Ａ When a plurality of R are present, they may be the same or different. ２１Ａ and R ２２Ａ , R ２２Ａ and R ２３Ａ , R ２３Ａ and R ２４Ａ , and ring L １Ａ The substituent that may be possessed by R ２１Ａ may be bonded to each other to form a ring together with the atoms to which they are bonded. Ring L ２Ａ represents a benzene ring, a pyridine ring, or a diazabenzene ring.

8. The polymer compound according to claim 7, wherein the metal complex represented by formula (1-A) is a metal complex represented by formula (1-B1), formula (1-B2), formula (1-B3), formula (1-B4), or formula (1-B5). 【Chemistry 13】 [In the formula, M, n １ , n ２ , R ２１Ａ , R ２２Ａ , R ２３Ａ , R ２４Ａ and A １ -G １ -A ２ has the same meaning as above. n １１ and n １２ Each independently represents 1 or 2. However, when M is a rhodium atom or an iridium atom, n １１ +n １２ is 3, and when M is a palladium atom or a platinum atom, n １１ +n １２ is 2. R １１Ｂ , R １２Ｂ , R １３Ｂ , R １４Ｂ , R １５Ｂ , R １６Ｂ , R １７Ｂ and R １８Ｂ R 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, or a halogen atom, and these groups may have a substituent. １１Ｂ , R １２Ｂ , R １３Ｂ , R １４Ｂ , R １５Ｂ , R １６Ｂ , R １７Ｂ and R １８Ｂ When multiple are present, they may be the same or different. In formula (1-B1), R １１Ｂ and R １２Ｂ , R １２Ｂ and R １３Ｂ , R １３Ｂ and R １４Ｂ , and R １１Ｂ and R ２１Ａ may be bonded to each other to form a ring together with the atom to which each is bonded. １３Ｂ and R １４Ｂ , R １３Ｂ and R １５Ｂ , R １５Ｂ and R １６Ｂ , R １６Ｂ and R １７Ｂ , R １７Ｂ and R １８Ｂ , and R １８Ｂ and R ２１Ａ may be bonded to each other to form a ring together with the atom to which each is bonded. １１Ｂ and R １２Ｂ , R １２Ｂ and R １３Ｂ , R １３Ｂ and R １４Ｂ , R １１Ｂ and R ２１Ａ , R １３Ｂ and R １５Ｂ , R １５Ｂ and R １６Ｂ , R １６Ｂ and R １７Ｂ , R １７Ｂ and R １８Ｂ , and R １８Ｂ and R ２１Ａ may be bonded to each other to form a ring together with the atom to which each is bonded. １１Ｂ and R １８Ｂ , R １４Ｂ and R １５Ｂ , R １５Ｂ and R １６Ｂ , R １６Ｂ and R １７Ｂ , R １７Ｂ and R １８Ｂ , and R １１Ｂ and R ２１Ａ may be bonded to each other to form a ring together with the atom to which they are bonded. １１Ｂ and R １２Ｂ , R １２Ｂ and R １８Ｂ , R １５Ｂ and R １６Ｂ , R １６Ｂ and R １７Ｂ , R １７Ｂ and R １８Ｂ , and R １１Ｂ and R ２１Ａ may be bonded to each other to form a ring together with the atoms to which they are bonded.

9. The polymer compound according to any one of claims 1 to 8, further comprising a constitutional unit represented by formula (X): 【Chemistry 14】 [In the formula, a Ｘ１ and a Ｘ２ each independently represents an integer of 0 or more. Ar Ｘ１ and Ar Ｘ３ each independently represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. 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 to each other, and these groups may have a substituent. Ｘ２ and Ar Ｘ４ When multiple are present, they may be the same or different. R Ｘ１ , R Ｘ２ and R Ｘ３ R 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 When multiple are present, they may be the same or different.

10. The polymer compound according to any one of claims 1 to 9, further comprising a structural unit having a crosslinking group selected from Group A of crosslinking groups. (Bridging group A group) 【Chemistry 15】 [In the formula, R ＸＬ represents a methylene group, an oxygen atom, or a sulfur atom; ＸＬ represents an integer of 0 to 5. ＸＬ When multiple are present, they may be the same or different. ＸＬ When there are a plurality of groups, they may be the same or different. *1 represents a bonding position. These bridging groups may have a substituent, and when there are a plurality of such substituents, they may be bonded to each other to form a ring together with the carbon atom to which each is bonded.

11. The polymer compound according to any one of claims 1 to 10, At least one selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, an antioxidant, and a solvent; A composition comprising:

12. A light-emitting device having an anode, a cathode, and an organic layer provided between the anode and the cathode, the organic layer being a layer containing a crosslinked product of the polymer compound according to any one of claims 1 to 10.

13. The light-emitting device according to claim 12 , further comprising a light-emitting layer provided between the organic layer and the cathode.

Images