Polymer compound, composition and light-emitting device

Abstract

To provide a polymer compound and a composition useful in manufacturing a light-emitting device with high external quantum efficiency.SOLUTION: A polymer compound includes: a constitutional unit having a group a condensed ring compound expressed by a formula (1) with one hydrogen atom removed therefrom; and at least one constitutional unit selected from a constitutional unit expressed by a formula (X) and a constitutional unit expressed by a formula (Y). An application of the polymer compound is also provided.SELECTED DRAWING: None

Description

[Technical Field]

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

[0002] Organic electroluminescence devices (hereinafter also referred to as light-emitting devices) can be suitably used for, for example, displays and lighting applications. For example, Patent Document 1 proposes a compound represented by formula (E1) as a light-emitting material to be used in the light-emitting layer of the light-emitting device. [ka] [Prior art documents] [Patent documents]

[0003] [Patent Document 1] International Publication No. 2022 / 034916 Summary of the Invention [Problem to be solved by the invention]

[0004] However, the external quantum efficiency of the light-emitting device produced using the compound described in Patent Document 1 was not necessarily sufficient.

[0005] Therefore, an object of one embodiment of the present disclosure is to provide a polymer compound and a composition that are useful for producing a light-emitting device with high external quantum efficiency. Another object of another embodiment of the present disclosure is to provide a light-emitting device using the polymer compound. [Means for solving the problem]

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

[11] . [1] A polymer compound comprising a structural unit having a group in which one or more hydrogen atoms have been removed from a fused ring compound represented by formula (1), and at least one structural unit selected from a structural unit represented by formula (X) and a structural unit represented by formula (Y). [ka] [In formula (1), X 1 represents >O, >N—R′, >C(—R″) 2 , >S or >Se. R' represents an optionally substituted aryl group, an optionally substituted monovalent heterocyclic group, an optionally substituted alkyl group, or an optionally substituted cycloalkyl group. R'' represents a hydrogen atom, an aryl group which may have a substituent, an alkyl group which may have a substituent, or a cycloalkyl group which may have a substituent. R' and R'' of the >N-R' and / or the >C(-R'')2 are X containing the R' and R''. 1 may be bonded to Z adjacent to any carbon atom to which is directly bonded via a linking group or a single bond. Z is -C(-R Z )= or -N=, and two adjacent Zs represent -C(-R Z )2-, -Si(-R Z )2-, -N(-R Z )-, -O-, -S- or -Se-, R Z is a hydrogen atom or a substituent, and R Z Adjacent groups in the R Z may form a ring together with the ring to which it is attached, and the ring formed may be substituted. Multiple occurrences of the symbol may be the same or different. [ka] [In formula (X), 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. When a plurality of such substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded. Ar X2 and Ar X4 are each independently an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, and these groups may have a substituent. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded. Ar X2 When a plurality of Ar are present, they may be the same or different. X4 When there are a plurality of groups, 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. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded. X2 When there are multiple R's, they may be the same or different. X3 When there are multiple, they may be the same or different. [ka] [In formula (Y), Ar Y1represents 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. When a plurality of such substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded. [2] X in the formula (1) 1 is >N-R'. [3] The polymer compound according to [2], wherein the fused ring compound represented by formula (1) is a compound represented by formula (1-1). [ka] [In formula (1-1), R Z and R' have the same meaning as above.] [4] Ar in formula (Y) Y1 is a phenylene group which may have a substituent, a fluorenediyl group which may have a substituent, or a group represented by formula (YY). [ka] [In formula (YY), Ar YY1 and Ar YY3 each independently represents an arylene group which may have a substituent, Ar YY2 represents a divalent nitrogen-containing aromatic heterocyclic group which may have a substituent.] [5] A composition comprising the polymer compound according to any one of [1] to [4] and a metal complex represented by formula (Z). [ka] [In formula (Z), M 1represents a ruthenium atom, a rhodium atom, a palladium atom, an iridium atom, or a platinum atom. n 1 represents an integer of 1 or greater, and n 2 represents an integer of 0 or more. However, M 1 When is a ruthenium atom, a rhodium atom, or an iridium atom, n 1 +n 2 is 3 and M 1 When is a palladium atom or a platinum atom, n 1 +n 2 is 2. E 1 and E 2 Each of E independently represents a nitrogen atom or a carbon atom. 1 and E 2 When there are a plurality of groups, they may be the same or different. Ring L 1 represents an aromatic heterocycle, and the ring 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 there are multiple groups, 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 the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded. Ring L 2 When there are multiple groups, they may be the same or different. Ring L 1 and the substituents which may be present on ring L 2 The substituents which may be possessed by the group may be bonded to each other to form a ring together with the atoms 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 A1 and A 2 A represents an atomic group that, together with A, constitutes a bidentate ligand. 1 -G 1 -A 2 When there are multiple, they may be the same or different. [6] A composition comprising 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, and the polymer compound according to any one of [1] to [4]. [7] A light-emitting device comprising an anode, a cathode, and an organic layer provided between the anode and the cathode, the organic layer containing the polymer compound according to any one of [1] to [4]. [8] The method includes a step of polymerizing a compound having a polymerizable group in the presence of a transition metal catalyst and an inorganic base, The compound having the polymerizable group has two or more boron atoms, a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, and sp 3 and at least one selected from the group consisting of carbon atoms, and a fused ring compound having a polymerizable group, wherein the fused heterocyclic ring skeleton satisfies at least one of requirements (i) and (ii). (i) The nitrogen atom, the oxygen atom, the sulfur atom, the selenium atom, and the sp 1 atom contained in the ring of the fused heterocyclic skeleton 3 The total number of carbon atoms is 4 or more. (ii) The number of nitrogen atoms contained in the ring of the fused heterocyclic skeleton is 2 or more. [9] The method for producing a polymer compound according to [8], wherein the fused ring compound having a fused heterocyclic skeleton is a fused ring compound represented by formula (BM-1): [ka] [In formula (BM-1), Ring R b1 , ring R b2 , ring R b3 , ring Rb4 and ring R b5 each independently represents an aromatic hydrocarbon ring or a heterocyclic ring, and these rings may have a substituent. When a plurality of such substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded. X b1 , X b2 , X b3 and X b4 are each independently an oxygen atom, a sulfur atom, a selenium atom, -N(R xb )-, an alkylene group, or a cycloalkylene group, and these groups may have a substituent. When a plurality of such substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded. Ring R b1 , ring R b2 , ring R b3 , ring R b4 , ring R b5 , X b1 , X b2 , X b3 and X b4 At least one of them has a polymerizable group. R xb 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. When a plurality of such substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded. X b1 and ring R b1 , X b1 and ring R b2 , X b2 and ring R b1 , X b2 and ring R b3 , X b3 and ring R b2 , X b3 and ring R b4 , X b4 and ring R b4 , X b4 and ring R b5 , ring R b2 and ring R b3, ring R b2 and ring R b5 , and ring R b3 and ring R b5 may each independently bond directly or via a divalent or higher valent group which may have a substituent to form a ring. When a plurality of such substituents are present, they may be the same or different and may bond to each other to form a ring together with the atom to which they are bonded.

[10] The method for producing a polymer compound according to [9], wherein the fused ring compound represented by formula (BM-1) is a fused ring compound represented by formula (BM-2). JPEG2025129031000009.jpg6388 [In formula (BM-2), Ring R b1 , ring R b2 , ring R b3 , ring R b4 , ring R b5 , X b2 and X b4 represents the same meaning as above. Ring R Xb1 and ring R Xb2 each independently represents an aromatic hydrocarbon ring or a heterocyclic ring, and these rings may have a substituent. When a plurality of such substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded. Ring R b1 , ring R b2 , ring R b3 , ring R b4 , ring R b5 , ring R Xb1 , ring R Xb2 , X b1 , X b2 , X b3 and X b4 At least one of them has a polymerizable group. Ring R Xb1 and ring R b1 , ring R Xb1 and ring R Xb2 , and ring R Xb2 and ring R b4may each independently bond directly or via a divalent or higher valent group which may have a substituent to form a ring. When a plurality of such substituents are present, they may be the same or different and may bond to each other to form a ring together with the atom to which they are bonded.

[11] The method for producing a polymer compound according to

[10] , wherein the fused ring compound represented by formula (BM-2) is a fused ring compound represented by formula (1M). [ka] [In formula (1M), X 1 represents >O, >N—R′, >C(—R″) 2 , >S or >Se. R' represents an optionally substituted aryl group, an optionally substituted monovalent heterocyclic group, an optionally substituted alkyl group, or an optionally substituted cycloalkyl group. R'' represents a hydrogen atom, an aryl group which may have a substituent, an alkyl group which may have a substituent, or a cycloalkyl group which may have a substituent. R' and R'' of the >N-R' and / or the >C(-R'')2 are X containing the R' and R''. 1 may be bonded to Z adjacent to any carbon atom to which is directly bonded via a linking group or a single bond. Z is -C(-R Z )= or -N=, and two adjacent Zs represent -C(-R Z )2-, -Si(-R Z )2-, -N(-R Z )-, -O-, -S- or -Se-, R Z is a hydrogen atom or a substituent, and R Z Adjacent groups in the R Z may form a ring together with the ring to which it is attached, and the ring formed may be substituted. Multiple Zs and Xs 1 At least one of them has a polymerizable group. Multiple occurrences of the symbol may be the same or different. [Effects of the Invention]

[0007] According to the present disclosure, it is possible to provide a polymer compound and a composition useful for producing a light-emitting device having high external quantum efficiency. Furthermore, according to the present disclosure, it is possible to provide a light-emitting device having high external quantum efficiency containing the composition. DETAILED DESCRIPTION OF THE INVENTION

[0008] Preferred embodiments of the present disclosure will be described in detail below.

[0009] <Explanation of common terms> Terms commonly used in this specification have the following meanings unless otherwise specified. 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. The hydrogen atom may be a deuterium atom or a proton atom. In the formula representing a metal complex, the solid line representing a bond with the metal means an ionic bond, a covalent bond, or a coordinate bond.

[0010] "Polymer compounds" are compounds that have a molecular weight distribution and have a number average molecular weight of 1 x 10 in terms of polystyrene. 3 or more (e.g., 1×10 3 ~1×10 8 ) means a polymer in which The polymer compound may be any of a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, or other forms. The terminal group of the polymer compound is preferably a stable group, since if the polymerization active group remains as it is, the light-emitting properties or luminance life may be reduced when the polymer compound is used to produce a light-emitting device. The terminal group of the polymer compound is preferably a group that is conjugated to the main chain, and examples thereof include an aryl group or a monovalent heterocyclic group that is bonded to the main chain of the polymer compound via a carbon-carbon bond. "Low molecular weight compounds" are compounds that do not have a molecular weight distribution and have a molecular weight of 1 x 10 4 The following compounds are meant: The term "structural unit" refers to a unit that exists in one or more instances in a polymer compound. A structural unit that exists in two or more instances in a polymer compound is generally also called a "repeating unit."

[0011] 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. Examples of the alkyl group 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, and a dodecyl group. The alkyl group may also be a group in which some or all of the hydrogen atoms in these groups have been substituted with a substituent (for example, 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-dihexylphenyl)propyl group, or a 6-ethyloxyhexyl group).

[0012] The number of carbon atoms in the "cycloalkyl group" is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20, not including the number of carbon atoms in the substituent. The cycloalkyl group may have a substituent. Examples of the cycloalkyl group include a cyclohexyl group, a cyclohexylmethyl group, a cyclohexylethyl group, and groups in which some or all of the hydrogen atoms in these groups have been substituted with substituents (e.g., an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, etc.).

[0013] An "aromatic hydrocarbon group" refers to a group obtained by removing one or more hydrogen atoms directly bonded to atoms constituting a ring from an aromatic hydrocarbon. A group obtained by removing one hydrogen atom directly bonded to atoms constituting a ring from an aromatic hydrocarbon is also called an "aryl group." A group obtained by removing two hydrogen atoms directly bonded to atoms constituting a ring from an aromatic hydrocarbon is also called an "arylene group." The number of carbon atoms in the aromatic hydrocarbon group is usually 6 to 60, preferably 6 to 40, and more preferably 6 to 20, not including the number of carbon atoms in the substituent. Examples of "aromatic hydrocarbon groups" include groups in which one or more hydrogen atoms directly bonded to ring atoms have been removed from monocyclic aromatic hydrocarbons (e.g., benzene) or polycyclic aromatic hydrocarbons (e.g., bicyclic aromatic hydrocarbons such as naphthalene and indene; tricyclic aromatic hydrocarbons such as anthracene, phenanthrene, dihydrophenanthrene, and fluorene; tetracyclic aromatic hydrocarbons such as benzanthracene, benzophenanthrene, benzofluorene, pyrene, and fluoranthene; pentacyclic aromatic hydrocarbons such as dibenzanthracene, dibenzophenanthrene, dibenzofluorene, perylene, and benzofluoranthene; hexacyclic aromatic hydrocarbons such as spirobifluorene; and heptacyclic aromatic hydrocarbons such as benzospirobifluorene and acenaphthofluoranthene). Aromatic hydrocarbon groups include groups in which multiple such groups are bonded. The aromatic hydrocarbon group may have a substituent.

[0014] The arylene group is preferably a group represented by formula (A-1) to formula (A-23): The arylene group includes groups in which a plurality of these groups are bonded. [ka] [ka] [ka] [ka] JPEG2025129031000015.jpg36124 In the formula, 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, and R a may be bonded to each other to form a ring together with the atoms to which they are bonded.

[0015] The "alkoxy group" may be either linear or branched. The number of carbon atoms in a linear alkoxy group, not including the number of carbon atoms in the substituent, is usually 1 to 40, and preferably 4 to 10. The number of carbon atoms in a branched alkoxy group, not including the number of carbon atoms in the substituent, is usually 3 to 40, and preferably 4 to 10. The alkoxy group may have a substituent. Examples of the alkoxy group 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 some or all of the hydrogen atoms in these groups have been substituted with substituents (for example, 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 in the substituents. The cycloalkoxy group may have a substituent, and examples thereof include a cyclohexyloxy group.

[0016] 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 in the substituent. 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 some or all of the hydrogen atoms in these groups have been substituted with substituents (for example, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a fluorine atom, or the like).

[0017] A "p-valent heterocyclic group" (p represents an integer of 1 or greater) refers to an atomic group remaining after removing p hydrogen atoms from a heterocyclic compound among the hydrogen atoms directly bonded to carbon atoms or heteroatoms constituting the ring. Among p-valent heterocyclic groups, a "p-valent aromatic heterocyclic group" which is an atomic group remaining after removing p hydrogen atoms from an aromatic heterocyclic compound among the hydrogen atoms directly bonded to carbon atoms or heteroatoms constituting the ring 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 also to a compound in which an aromatic ring is condensed with a heterocycle, even if the heterocycle itself does not exhibit aromaticity, such as phenoxazine, phenothiazine, dibenzoborole, dibenzosilole, or benzopyran.

[0018] The number of carbon atoms in the monovalent heterocyclic group is usually 2 to 60, and preferably 4 to 20, not including the number of carbon atoms in 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 some or all of the hydrogen atoms in these groups have been substituted with substituents (for example, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like).

[0019] 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. Examples of the divalent heterocyclic group include divalent groups formed by removing two hydrogen atoms directly bonded to carbon atoms or heteroatoms constituting the ring from pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilole, phenoxazine, phenothiazine, acridine, dihydroacridine, furan, thiophene, azole, diazole, or triazole. The divalent heterocyclic group is preferably a group represented by formula (AA-1) to formula (AA-34). The divalent heterocyclic group includes a group formed by bonding a plurality of these groups. [ka] [ka] [ka] [ka] [ka] [ka] [ka] In the formula, R and R a represents the same meaning as above.

[0020] The term "halogen atom" refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0021] The "amino group" may have a substituent, and is preferably a substituted amino group (preferably a secondary amino group or a tertiary amino group, more preferably a tertiary amino group). The substituent that the amino group has is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may further have a substituent. When the amino group has multiple substituents, they may be the same or different, and may be bonded to each other to form a ring together with the nitrogen atom to which they are bonded. Examples of the substituted amino group include a dialkylamino group, a dicycloalkylamino group, a diarylamino group, and groups in which some or all of the hydrogen atoms in these groups have been further substituted with substituents. Examples of the substituted 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.

[0022] 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 the "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 the cycloalkenyl group may have a substituent. Examples of the alkenyl group 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 some or all of the hydrogen atoms in these groups have been substituted with a substituent. Examples of the cycloalkenyl group include a cyclohexenyl group, a cyclohexadienyl group, a cyclooctatrienyl group, a norbornylenyl group, and groups in which some or all of the hydrogen atoms in these groups have been substituted with a substituent.

[0023] The "alkynyl group" may be either linear or branched. The number of carbon atoms in the alkynyl group, not including the carbon atoms of the substituents, is usually 2 to 20, and preferably 3 to 20. The number of carbon atoms in a branched alkynyl group, not including the carbon atoms of the substituents, is usually 4 to 30, and 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 the cycloalkynyl group may have a substituent. Examples of the alkynyl group 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 some or all of the hydrogen atoms in these groups have been substituted with a substituent. Examples of the cycloalkynyl group include a cyclooctynyl group and groups in which some or all of the hydrogen atoms in this group have been substituted with a substituent.

[0024] The "crosslinking group" refers to a group that can generate a new bond by being subjected to heat treatment, ultraviolet irradiation treatment, near-ultraviolet irradiation treatment, visible light irradiation treatment, infrared irradiation treatment, a radical reaction, or the like, and is preferably a crosslinking group represented by formula (XL-1) to formula (XL-19) in Crosslinking Group Group A, more preferably a crosslinking group represented by formula (XL-1), formula (XL-3), formula (XL-9), formula (XL-10), formula (XL-16), or formula (XL-17) to formula (XL-19), even more preferably a crosslinking group represented by formula (XL-1), formula (XL-16), or formula (XL-17) to formula (XL-19), and particularly preferably a crosslinking group represented by formula (XL-1) or formula (XL-17). [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 there are multiple n, they may be the same or different. XL When there are multiple groups, they may be the same or different. *1 indicates the bonding position. These bridging groups may have a substituent, and when there are multiple groups, they may be the same or different and may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.

[0025] The "substituent" is preferably 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. When multiple substituents are present, they may be the same or different. When multiple substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded, but it is preferable that they do not form a ring.

[0026] <Polymer compounds> The polymer compound of the present disclosure comprises a first structural unit having a group in which one or more hydrogen atoms have been removed from a fused ring compound represented by formula (1) (hereinafter also referred to as "a compound represented by formula (1)"), and at least one structural unit selected from a second structural unit represented by formula (X) and a third structural unit represented by formula (Y). The polymer compound of the present disclosure may contain only one type or two or more types of first structural units, may contain only one type or two or more types of second structural units, and may contain only one type or two or more types of third structural units, and the first structural unit, second structural unit, and third structural unit are different. [First structural unit] [ka] [In formula (1), X 1 represents >O, >N—R′, >C(—R″) 2 , >S or >Se. R' represents an optionally substituted aryl group, an optionally substituted monovalent heterocyclic group, an optionally substituted alkyl group, or an optionally substituted cycloalkyl group. R'' represents a hydrogen atom, an aryl group which may have a substituent, an alkyl group which may have a substituent, or a cycloalkyl group which may have a substituent. R' and R'' of the >N-R' and / or the >C(-R'')2 are X containing the R' and R''. 1 may be bonded to Z adjacent to any carbon atom to which is directly bonded via a linking group or a single bond. Z is -C(-R Z )= or -N=, and two adjacent Zs represent -C(-R Z )2-, -Si(-R Z )2-, -N(-R Z )-, -O-, -S- or -Se-, R Z is a hydrogen atom or a substituent, and R Z Adjacent groups in the R Zmay form a ring (preferably an aromatic hydrocarbon ring or a heterocyclic ring) together with the ring to which it is bonded, and the ring formed may be substituted. Multiple occurrences of the symbol may be the same or different.

[0027] Two adjacent Zs are -C(-R Z )2-, -Si(-R Z )2-, -N(-R Z Examples of the ring structure having Z substituted with -C(-R)-, -O-, -S-, or -Se- include a cyclopentadiene ring, a pyrrole ring, a furan ring, a thiophene ring, a thiazole ring, an oxazole ring, and a selenadiazole ring. However, two adjacent Zs may not be -C(-R)-, -O-, -S-, or -Se-. Z )2-, -Si(-R Z )2-, -N(-R Z In this case, it is preferable that Z at the ortho or para position relative to the boron atom is not replaced by -C(-R Z )= is preferable. In addition, in a ring (monocyclic ring) containing Z which is -N=, it is preferable that one or two of the multiple Zs are -N=, and when two are -N=, it is preferable that the two -N= are not adjacent to each other. When a six-membered ring having four Zs contains -N= as Z, the six-membered ring having four Zs is preferably a pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, or 1,2,3-triazine ring, more preferably a pyridine ring, pyrazine ring, or pyrimidine ring. The number of rings (monocyclic rings) containing -N= as Z is preferably 0 to 4, more preferably 0 to 3, still more preferably 0 to 2, and particularly preferably 0 to 1. X 1 Alternatively, it is preferred that Z is -N= in the ortho or para position relative to the carbon atom to which >N- is bonded. In one embodiment, each Z is —C(—R Z )=, that is, both rings are benzene rings which may have a substituent.

[0028] Z is -C(-R Z ) = R Zare each preferably independently a hydrogen atom, an aromatic hydrocarbon group, a monovalent heterocyclic group, a substituted amino group, an alkyl group, or a cycloalkyl group. Z R may be bonded to each other to form a ring (preferably an aromatic hydrocarbon ring or a heterocyclic ring) together with the adjacent ring, and at least one hydrogen atom in the formed ring may be substituted with an aromatic hydrocarbon group, an alkyl group, or a cycloalkyl group. Z are each independently more preferably a hydrogen atom, an aromatic hydrocarbon group, a substituted amino group, an alkyl group, or a cycloalkyl group, further preferably a hydrogen atom, an aromatic hydrocarbon group, a substituted amino group, or an alkyl group, and particularly preferably a hydrogen atom, an aromatic hydrocarbon group, or an alkyl group.

[0029] R attached to adjacent carbon atoms Z They may be bonded to each other to form a ring (preferably an aromatic hydrocarbon ring or a heterocyclic ring) together with a ring containing the carbon atom.

[0030] Examples of the structure of the ring containing Z in formula (1) are shown below as examples of a structure containing four Zs and bonded to a boron atom and a nitrogen atom. In the following formula, R represents R Z However, it does not mean that R is bonded to another R. Furthermore, n is an integer of 0 to 4, and R n and R C is a hydrogen atom, an aryl group optionally substituted with an alkyl group or a cycloalkyl group, a monovalent heterocyclic group optionally substituted with an alkyl group or a cycloalkyl group, an alkyl group optionally substituted with a cycloalkyl group, or a cycloalkyl group optionally substituted with an alkyl group, and two R C may be bonded to each other to form a ring. Regarding the ring to be formed, X 1 When two R′′s in C(—R′′)2 are bonded to each other to form a ring, the explanation below can be seen.

[0031] [ka] JPEG2025129031000026.jpg128166

[0032] X 1 In the above, R' in >N-R' and R'' in >C(-R'')2 are X containing the R' and R''. 1 may be bonded to Z adjacent to any carbon atom to which is directly bonded via a linking group or a single bond (these are also collectively referred to as a bonding group). Examples of the linking group include -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C=C-, -N(-R)-, -O-, -S-, or -C(-R)2-. Examples of >C(-R'') forming a ring include the following structures. Preferably, R in -CHR-CHR-, R in -CR-CR-, R in -CR=CR-, R in -N(-R)-, and R in -C(-R)- are each independently a hydrogen atom, an aryl group, a monovalent heterocyclic group, an alkyl group, an alkenyl group, an alkynyl group, or a cycloalkyl group. At least one hydrogen atom in the R may be substituted with an alkyl group or a cycloalkyl group. Two Rs (preferably two adjacent Rs) may form a ring to form a cycloalkylene group, an arylene group, or a divalent heterocyclic group.

[0033] [ka]

[0034] The linking group is preferably a single bond, or -CR=CR-, -N(-R)-, -O-, -S-, or -C(-R)2- as a linking group, more preferably a single bond, or -CR=CR-, -N(-R)-, -O-, or -S- as a linking group, and still more preferably a single bond.

[0035] The positions at which two R's are bonded by the bonding group are not particularly limited as long as they are bondable positions, but they are preferably bonded at the positions closest to each other. For example, when two R's are phenyl groups, they are preferably bonded at positions ortho (2-position) relative to the bonding position (1-position) of "C" in the phenyl groups.

[0036] X 1 represents >O, >N-R', >C(-R'')2, >S or >Se, preferably >N-R', >O, >S or >Se, more preferably >N-R', >O or >S, even more preferably >N-R' or >S, and particularly preferably >N-R'.

[0037] R' represents an aryl group which may have a substituent, a monovalent heterocyclic group which may have a substituent, an alkyl group which may have a substituent, or a cycloalkyl group which may have a substituent, and is more preferably an aryl group which may have a substituent. The aryl group is preferably a phenyl group, a biphenyl group (particularly a 2-biphenyl group), or a terphenyl group (particularly a phenyl-2'-yl group), and more preferably a phenyl group or a biphenyl group. When the aryl group is substituted, the substituent is preferably a methyl group or a tert-alkyl group. The number of substituents in the aryl group is preferably 0 to 3, and more preferably 0 to 2. R' is particularly preferably an unsubstituted phenyl group, a phenyl group having methyl groups bonded to the meta or para position, or a phenyl group having methyl groups bonded to one or two ortho positions.

[0038] The tert-alkyl group is represented by the following formula (tR): [ka] In the formula (tR), R a , R b and R care each independently an alkyl group having 1 to 24 carbon atoms, any —CH2— in the alkyl may be substituted with —O—, and the group represented by formula (tR) substitutes at least one hydrogen atom in the structure represented by formula (1) at *.

[0039] R a , R b and R c The "alkyl group having 1 to 24 carbon atoms" may be either a straight chain or a branched chain, and examples thereof include a straight chain alkyl group having 1 to 24 carbon atoms or a branched chain alkyl group having 3 to 24 carbon atoms, an alkyl group having 1 to 18 carbon atoms (branched chain alkyl group having 3 to 18 carbon atoms), an alkyl group having 1 to 12 carbon atoms (branched chain alkyl group having 3 to 12 carbon atoms), an alkyl group having 1 to 6 carbon atoms (branched chain alkyl group having 3 to 6 carbon atoms), and an alkyl group having 1 to 4 carbon atoms (branched chain alkyl group having 3 to 4 carbon atoms).

[0040] In the formula (tR), R a , R b and R c The total number of carbon atoms is preferably 3 to 20, and more preferably 3 to 10.

[0041] R a , R b and R cExamples of the alkyl group represented by the formula (I) include a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, an isobutyl group, a secondary butyl group, a tert-butyl group, a normal pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a normal hexyl group, a 1-methylpentyl group, a 4-methyl-2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, a normal heptyl group, a 1-methylhexyl group, a normal octyl group, a tert-octyl group, a 1-methylheptyl group, a Examples of the alkyl group include normal hexyl, 2-ethylhexyl, 2-propylpentyl, normal nonyl, 2,2'-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, normal decyl, normal undecyl, 1-methyldecyl, normal dodecyl, normal tridecyl, 1-hexylheptyl, normal tetradecyl, normal pentadecyl, normal hexadecyl, normal heptadecyl, normal octadecyl, and normal eicosyl groups.

[0042] Examples of the group represented by formula (tR) include a tert-butyl group, a tert-amyl group, a 1-ethyl-1-methylpropyl group, a 1,1'-diethylpropyl group, a 1,1-dimethylbutyl group, a 1-ethyl-1-methylbutyl group, a 1,1,3,3-tetramethylbutyl group, a 1,1,4-trimethylpentyl group, a 1,1,2-trimethylpropyl group, a 1,1-dimethyloctyl group, a 1,1-dimethylpentyl group, a 1,1-dimethylheptyl group, a 1,1,5-trimethylhexyl group, a 1 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl, etc. Of these, the group represented by formula (tR) is preferably a tert-butyl group or a tert-amyl group.

[0043] Examples of the compound represented by formula (1) include compounds represented by formulas (1-101) to (1-102) and (1-104) to (1-154).

[0044] [ka] JPEG2025129031000030.jpg207158 JPEG2025129031000031.jpg224142 JPEG2025129031000032.jpg226139 JPEG2025129031000033.jpg44111

[0045] The compound represented by formula (1) is preferably a compound represented by formula (1-1). Z and R' have the same meaning as above.

[0046] The first structural unit is preferably a structural unit having a group obtained by removing 1 to 5 hydrogen atoms from a compound represented by formula (1), because it allows for easy synthesis of the polymer compound, more preferably a structural unit having a group obtained by removing 1 to 3 hydrogen atoms from a compound represented by formula (1), and even more preferably a structural unit having a group obtained by removing 1 or 2 hydrogen atoms from a compound represented by formula (1). Note that the group obtained by removing 1 or more hydrogen atoms from a compound represented by formula (1) may be a group obtained by removing 1 or more hydrogen atoms from a substituent that the compound represented by formula (1) may have.

[0047] The first constitutional unit is a benzene ring of any of the compounds represented by formula (1-1) and X 1 It is preferable that the structural unit has a group in which two hydrogen atoms have been removed, selected from the group represented by R' in >N-R' and the group represented by R'' in >C(-R'')2.

[0048] Examples of the first constitutional unit include compounds represented by formulae (1-1101) to (1-1114). [ka] JPEG2025129031000035.jpg174151

[0049] The first structural unit provides excellent external quantum efficiency to the light-emitting device, and therefore the amount of the first structural unit is preferably 0.01 to 50 mol %, more preferably 0.05 to 10 mol %, even more preferably 0.1 to 5 mol %, and particularly preferably 0.2 to 3 mol %, relative to the total amount of structural units contained in the polymer compound containing the first structural unit.

[0050] [Second building block] The second constitutional unit contained in the polymer compound of the present disclosure is a constitutional unit represented by formula (X).

[0051] The polymer compound may contain only one type of constitutional unit represented by formula (X), or two or more types of constitutional units. [ka] [In the formula, a X1 and a X2 Each independently represents an integer of 0 or more. X1 and Ar X3 each independently represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. X2 and Ar X4 each independently represents an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, and these groups may have a substituent. X2 and Ar X4 When there are multiple R's, they may be the same or different. X1 , R X2 and R X3R 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. X1 , R X2 and R X3 When there are multiple, they may be the same or different.

[0052] a X1 is preferably 2 or less, and more preferably 1, since the external quantum efficiency of the light-emitting device is excellent.

[0053] a X2 is preferably 2 or less, and more preferably 0, since the external quantum efficiency of the light-emitting device is excellent.

[0054] R X1 , R X2 and R X3 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.

[0055] Ar X1 and Ar X3 The arylene group represented by the formula (A-1) is more preferably a group represented by formula (A-9), and even more preferably a group represented by formula (A-1), and these groups may have a substituent.

[0056] Ar X1 and Ar X3 The divalent heterocyclic group represented by the formula (AA-1) is more preferably a group represented by any one of formulas (AA-1), (AA-2), and (AA-7) to (AA-26), and these groups may have a substituent.

[0057] Ar X1 and Ar X3 is preferably an arylene group which may have a substituent.

[0058] Ar X2 and Ar X4The arylene group represented by the formula (A-1) is more preferably a group represented by any one of formulas (A-1), (A-6), (A-7), (A-9) to (A-11), or formula (A-19), and these groups may have a substituent.

[0059] Ar X2 and Ar X4 A more preferred range of the divalent heterocyclic group represented by Ar X1 and Ar X3 The more preferred range is the same as that of the divalent heterocyclic group represented by the following formula:

[0060] 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, the more preferred ranges and even more preferred ranges of the arylene group and the divalent heterocyclic group are, respectively, Ar X1 and Ar X3 The more preferred and even more preferred ranges are the same as those of the arylene group and divalent heterocyclic group represented by the following formula:

[0061] Ar X2 and Ar X4 As the divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, Ar Y1 and at least one divalent heterocyclic group directly bonded to each other.

[0062] Ar X2 and Ar X4 is preferably an arylene group which may have a substituent.

[0063] Ar X1 ~Ar X4 and R X1 ~R X3 The substituent that the group represented by the formula (I) may have is preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups may further have a substituent.

[0064] The structural unit represented by formula (X) is preferably a structural unit represented by any one of formulas (X-1) to (X-7), more preferably a structural unit represented by any one of formulas (X-1) to (X-6), and even more preferably a structural unit represented by any one of formulas (X-3) to (X-6).

[0065] [ka]

[0066] [ka]

[0067] [ka]

[0068] [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 attached.

[0069] Examples of the constitutional unit represented by formula (X) include constitutional units represented by any of formulas (X1-1) to (X1-23), and preferably constitutional units represented by any of formulas (X1-3) to (X1-10).

[0070] [ka]

[0071] [ka]

[0072] [ka]

[0073] [ka]

[0074] [ka]

[0075] [ka]

[0076] [ka]

[0077] [Third structural unit] The third constitutional unit contained in the polymer compound of the present disclosure is a constitutional unit represented by formula (Y).

[0078] [ka] [In formula (Y), 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. When a plurality of such substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded.

[0079] The substituent is preferably an alkyl group, a cycloalkyl group, an aryl group, an alkoxy group, a cycloalkoxy group, an aryloxy group, a monovalent heterocyclic group, an amino group, or a crosslinking group, more preferably an alkyl group, an aryl group, a monovalent heterocyclic group, or an amino group, and even more preferably an alkyl group or an aryl group.

[0080] In formula (Y), Ar Y1 The arylene group represented by the following formula is preferably a phenylene group which may have a substituent, or a fluorenediyl group which may have a substituent.

[0081] Ar Y1 The arylene group represented by the formula (A-1) is preferably a group represented by formula (A-1), formula (A-2), any one of formulas (A-6) to (A-10), formula (A-19) or formula (A-20), and more preferably a group represented by formula (A-1), formula (A-2), formula (A-7), formula (A-9) or formula (A-19).

[0082] Ar Y1 Examples of the divalent group in which at least one arylene group represented by the formula (I) and at least one divalent heterocyclic group are directly bonded to each other include divalent groups represented by the formula (I): [ka] [In the formula, R XX represents a hydrogen atom, an alkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent.]

[0083] R XX is preferably an alkyl group or an aryl group, and these groups may have a substituent.

[0084] Ar Y1 As the divalent group in which at least one arylene group represented by the formula (YY) is directly bonded to at least one divalent heterocyclic group, a group represented by the formula (YY) is preferred.

[0085] [ka] [In formula (YY), Ar YY1 and Ar YY3 each independently represents an arylene group which may have a substituent, Ar YY2 represents a divalent nitrogen-containing aromatic heterocyclic group which may have a substituent.]

[0086] In formula (YY), Ar YY1 and Ar YY3 As the arylene group in the formula (I), a phenylene group, a biphenylene group, a naphthalenediyl group, a phenanthrenediyl group, a dihydrophenanthrenediyl group, a fluorenediyl group, and a pyrenediyl group are preferred, a phenylene group, a biphenylene group, a phenanthrenediyl group, a dihydrophenanthrenediyl group, and a fluorenediyl group are more preferred, and a phenylene group and a biphenylene group are even more preferred, and these groups may have a substituent.

[0087] In formula (YY), Ar YY2 The divalent nitrogen-containing aromatic heterocyclic group in the above means a divalent group obtained by removing two hydrogen atoms from a compound having a nitrogen-containing aromatic heterocycle, among the hydrogen atoms directly bonded to the carbon atoms and heteroatoms constituting the nitrogen-containing aromatic heterocycle. Examples of compounds having a nitrogen-containing aromatic heterocycle include pyridine, diazabenzene, triazine, carbazole, dibenzofuran, dibenzothiophene, dibenzosilole, phenoxazine, phenothiazine, acridine, and dihydroacridine, with triazine and carbazole being preferred, and triazine being more preferred.

[0088] Ar Y1The divalent group in which at least one arylene group represented by the formula (I) and at least one divalent heterocyclic group are directly bonded may have a substituent, and the substituent is preferably an alkyl group, a cycloalkyl group, an aryl group, an alkoxy group, a cycloalkoxy group, an aryloxy group, a monovalent heterocyclic group, an amino group, or a bridging group, more preferably an alkyl group, an aryl group, a monovalent heterocyclic group, or an amino group, and even more preferably an alkyl group or an aryl group. These groups may have a substituent. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded.

[0089] The constitutional unit represented by formula (Y) may be a group in which two or more types of arylene groups are directly bonded.

[0090] Examples of the structural unit represented by formula (Y) include structural units represented by any of formulas (Y-1) to (Y-7). From the viewpoint of achieving better external quantum efficiency of the light-emitting device, a structural unit represented by any of formulas (Y-1) to (Y-3) is preferred, and from the viewpoint of electron transport properties, a structural unit represented by any of formulas (Y-4) to (Y-7) is preferred.

[0091] [ka] [In the formula, R Y1 represents a hydrogen atom, an alkyl group, an alkoxy 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 attached.

[0092] R Y1 is preferably a hydrogen atom, an alkyl group or an aryl group, and these groups may have a substituent.

[0093] The polymer compound of the present disclosure may contain only one type of constitutional unit represented by formula (Y-1), or may contain two or more types, and preferably contains two or more types.

[0094] The constitutional unit represented by formula (Y-1) may be a constitutional unit represented by formula (Y-1'). [ka] [In the formula, R Y11 represents an alkyl group, an alkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. Y11 may be the same or different.]

[0095] R Y11 is preferably an alkyl group or an aryl group, more preferably an alkyl group, and these groups may have a substituent.

[0096] [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, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. Y2 may be the same or different, and R Y2 may be bonded to each other to form a ring together with the carbon atoms to which they are attached.

[0097] X Y1 is -C(R Y2 )2- or -C(R Y2 )=C(R Y2)-, and -C(R Y2 )2- is more preferred.

[0098] R Y2 is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably an alkyl group or an aryl group, and these groups may have a substituent. The substituent that the alkyl group or aryl group may have is preferably an alkyl group or an aryl group, and these may further have a substituent.

[0099] X Y1 In the -C(R Y2 Two R in the group represented by )2- Y2 The combination of R is preferably such that both are alkyl groups, both are aryl groups, both are monovalent heterocyclic groups, or one is an alkyl group and the other is an aryl group or a monovalent heterocyclic group, and more preferably such that both are aryl groups, or one is an alkyl group and the other is an aryl group, and these groups may have a substituent. The substituent that the aryl group may have is preferably an alkyl group or an aryl group (more preferably an aryl group), and the substituent that the alkyl group may have is preferably an alkyl group or an aryl group, which may further have a substituent. When two R exist, Y2 may be bonded to each other to form a ring together with the atoms to which they are bonded, and R Y2 When forms a ring, -C(R Y2 The group represented by formula (Y-2-) is preferably a group represented by any one of formulas (Y-A1) to (Y-A5), more preferably a group represented by formula (Y-A4), and these groups may have a substituent. [ka]

[0100] X Y1 In the -C(R Y2 )=C(R Y2 Two R in the group represented by Y2In the combination of the above, both are preferably alkyl groups, or one is an alkyl group and the other is an aryl group, and these groups may have a substituent.

[0101] X Y1 In the -C(R Y2 )2-C(R Y2 )2-, where R Y2 is preferably an alkyl 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, and R Y2 When forms a ring, -C(R Y2 )2-C(R Y2 The group represented by (Y-B2)2- is preferably a group represented by any one of formulae (Y-B1) to (Y-B5), more preferably a group represented by formula (Y-B3), and these groups may have a substituent. [ka] [In the formula, R Y2 has the same meaning as above.]

[0102] The constitutional unit represented by formula (Y-2) may be a constitutional unit represented by formula (Y-2'). [ka] [In the formula, R Y1 and X Y1 has the same meaning as above.]

[0103] [ka] [In the formula, R Y1 and X Y1 has the same meaning as above.]

[0104] The constitutional unit represented by formula (Y-3) may be a constitutional unit represented by formula (Y-3'). [ka] [In the formula, R Y11 and X Y1 has the same meaning as above.]

[0105] [ka] [ka] [In the formula, R Y1 has the same meaning as above. Y3 represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent.]

[0106] R Y3 is preferably an alkyl group, an alkoxy group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups may have a substituent.

[0107] The constitutional unit represented by formula (Y-4) may be a constitutional unit represented by formula (Y-4'), and the constitutional unit represented by formula (Y-6) may be a constitutional unit represented by formula (Y-6'). [ka] [In the formula, R Y1 and R Y3 has the same meaning as above.]

[0108] Examples of the structural unit represented by formula (Y) include a structural unit composed of an arylene group represented by any one of formulas (Y-101) to (Y-134), and a structural unit composed of a divalent group in which at least one arylene group represented by any one of formulas (Y-301) to (Y-309) and at least one divalent heterocyclic group are directly bonded to each other. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] JPEG2025129031000075.jpg4655

[0109] [Other explanations] In the polymer compound of the present disclosure, the second constitutional unit represented by formula (X) provides excellent external quantum efficiency of the light-emitting device, and therefore the amount of the second constitutional unit represented by formula (X) is preferably 0 to 50 mol %, more preferably 0 to 40 mol %, and even more preferably 0 to 15 mol %, relative to the total amount of all constitutional units of the polymer compound.

[0110] In the polymer compound of the present disclosure, Ar Y1 The content of the third structural unit, which is an arylene group, relative to the total amount of all structural units of the polymer compound is preferably 10 to 95 mol %, and more preferably 30 to 90 mol %, in order to achieve better external quantum efficiency of the light-emitting device.

[0111] In the polymer compound of the present disclosure, Ar Y1 However, the content of the second structural unit, which is a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, is preferably 0.5 to 99.8 mol %, and more preferably 10 to 99.5 mol %, relative to the total amount of all structural units of the polymer compound, in order to achieve better external quantum efficiency of the light-emitting element.

[0112] Examples of the polymer compound of the present disclosure include polymer compounds P-1 to P-4 shown in Table 1.

[0113] [Table 1] [In Table 1, p, q, r, and s represent the molar ratio of each structural unit. p+q+r+s=100, and 70≦p+q+r≦100. Other structural units refer to structural units other than the first structural unit, the structural unit represented by formula (X), and the structural unit represented by formula (Y)]

[0114] In the present disclosure, the weight average molecular weight (Mw) of the polymer compound in terms of polystyrene is preferably 5.0×10 because it provides a light-emitting device with superior external quantum efficiency. 3 ~1.0×10 6 and more preferably 1.0 × 10 4 ~5.0×105 and more preferably 1.0 × 10 4 ~4.0×10 5 and particularly preferably 1.0 × 10 4 ~3.5×10 5 is.

[0115] The terminal group of the polymer compound of the present disclosure is preferably a stable group, since if the polymerization active group remains as it is, the light-emitting properties or luminance life may be reduced when the polymer compound is used to produce a light-emitting device. The terminal group of the polymer compound is preferably a group that is conjugated to the main chain, and examples thereof include an aryl group or a monovalent heterocyclic group that is bonded to the main chain of the polymer compound via a carbon-carbon bond.

[0116] The polymer compound of the present disclosure may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, or may have other forms, but is preferably a copolymer obtained by copolymerizing a plurality of types of raw material monomers.

[0117] <Method of manufacturing polymer compounds> Next, a method for producing the polymer compound of the present disclosure will be described. The polymer compound of the present disclosure can be produced, for example, by condensation polymerization of a compound represented by formula (M-1) and a compound represented by formula (M-3), condensation polymerization of a compound represented by formula (M-1) and a compound represented by formula (M-4), condensation polymerization of a compound represented by formula (M-3) and a compound represented by formula (M-2), condensation polymerization of a compound represented by formula (M-3) and a compound represented by formula (M-4), condensation polymerization of a compound represented by formula (M-1), a compound represented by formula (M-2), and a compound represented by formula (M-3), condensation polymerization of a compound represented by formula (M-1), a compound represented by formula (M-2), and a compound represented by formula (M-4), condensation polymerization of a compound represented by formula (M-1), a compound represented by formula (M-3), and a compound represented by formula (M-4), or condensation polymerization of a compound represented by formula (M-1), a compound represented by formula (M-2), a compound represented by formula (M-3), and a compound represented by formula (M-4). In this specification, compounds used in the production of polymer compounds may be collectively referred to as "raw material monomers." In the method for producing a polymer compound according to the present disclosure, the compound represented by formula (M-1), the compound represented by formula (M-2), the compound represented by formula (M-3), and the compound represented by formula (M-4) may each be used alone or in combination of two or more. [ka] [ka] [ka] [ka] [In the formula, Ar Y1 represents the same meaning as above. Ar Y2 represents a group obtained by removing two hydrogen atoms from the fused ring compound (1-1). Z C1 ~Z C4each independently represents a group selected from the group consisting of Substituent Group A and Substituent Group B.

[0118] 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.

[0119] For example, Z C1 and Z C2 is a group selected from the substituent group B, Z C3 and Z C4 is selected from the substituent group A.

[0120] For example, Z C1 and Z C3 is a group selected from the substituent group A, Z C2 and Z C4 is selected from the substituent group B.

[0121] <Substituent group A> Chlorine atom, bromine atom, iodine atom, and -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.

[0122] <Substituent group B> A boronic acid group or a boronic ester residue, preferably -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 and boron atom to which they are bonded; a group represented by -BF3Q' (wherein Q' represents Li, Na, K, Rb, or Cs); a group represented by —MgY′ (wherein Y′ represents a chlorine atom, a bromine atom, or an iodine atom); a group represented by -ZnY″ (wherein Y″ represents a chlorine atom, a bromine atom, or an iodine atom); and -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.

[0123] -B(OR C2 Examples of the group represented by formula 2 include groups represented by the following formulas: [ka]

[0124] A compound having a group selected from Substituent Group A and a compound having a group selected from Substituent Group B undergo condensation polymerization by a known coupling reaction, thereby bonding together carbon atoms bonded to the group selected from Substituent Group A and the group selected from Substituent Group B. Therefore, by subjecting a compound having two groups selected from Substituent Group A and a compound having two groups selected from Substituent Group B to a known coupling reaction, a condensation polymer of these compounds can be obtained by condensation polymerization.

[0125] The condensation polymerization is usually carried out in the presence of a catalyst, a base and a solvent, but may be carried out in the coexistence of a phase transfer catalyst, if necessary.

[0126] Examples of catalysts 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 containing ligands such as triphenylphosphine, tri(o-tolyl)phosphine, tri(tert-butyl)phosphine, tricyclohexylphosphine, 1,3-bis(diphenylphosphino)propane, and bipyridyl. The catalysts may be used alone or in combination of two or more.

[0127] The amount of 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 raw material monomers.

[0128] 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, methyltrioctylammonium chloride, etc. The base and phase transfer catalyst may each be used alone or in combination of two or more.

[0129] 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.

[0130] 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 solvents may be used alone or in combination of two or more.

[0131] 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.

[0132] The reaction temperature for the condensation polymerization is usually −100 to 200° C. The reaction time for the condensation polymerization is usually 1 hour or longer.

[0133] Post-treatment of the polymerization reaction can be carried out by any of known methods, such as a method of removing water-soluble impurities by liquid separation, a method of adding the reaction solution after the polymerization reaction to a lower alcohol such as methanol, filtering the precipitate, and then drying it, or a combination of these methods. When the purity of the polymer compound is low, it can be purified by a conventional method such as crystallization, reprecipitation, continuous extraction using a Soxhlet extractor, column chromatography, etc.

[0134] <Composition> The polymer compound of the present disclosure can be used as a composition capable of forming a light-emitting device having superior external quantum efficiency by combining it with a metal complex. The composition of the present disclosure includes, for example, the polymer compound of the present disclosure and a metal complex.

[0135] [Metal complexes] As the metal complex, the compound represented by formula (Z) is preferred because it provides a light-emitting device with superior external quantum efficiency.

[0136] [ka] [In the formula, M 1 represents a ruthenium atom, a rhodium atom, a palladium atom, an iridium atom, or a platinum atom. n 1represents an integer of 1 or greater, and n 2 represents an integer of 0 or more. However, M 1 When is a ruthenium atom, a rhodium atom, or an iridium atom, n 1 +n 2 is 3 and M 1 When is a palladium atom or a platinum atom, n 1 +n 2 is 2. E 1 and E 2 each independently represents a nitrogen atom or a carbon atom. Ring L 1 and ring L 2 each independently represents an aromatic hydrocarbon ring or an aromatic heterocycle, and these rings may have a substituent. When a plurality of such substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded. 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 Together with represents the atomic group that constitutes a bidentate ligand. In formula (Z), multiple symbols may have the same meaning or different meanings.

[0137] In formula (Z), M 1 is preferably an iridium atom. 1 and E 2 is preferably a carbon atom.

[0138] Ring L 1 is a 5- or 6-membered aromatic heterocycle, and these rings may have a substituent.

[0139] Ring L 2is preferably a 5- or 6-membered aromatic hydrocarbon ring or a 5- or 6-membered aromatic heterocyclic ring, more preferably a 6-membered aromatic hydrocarbon ring or a 6-membered aromatic heterocyclic ring, and even more preferably a 6-membered aromatic hydrocarbon ring, and these rings may have a substituent. 2 When E is a 6-membered aromatic heterocycle, 2 is preferably a carbon atom.

[0140] Ring L 1 and ring L 2 is preferably a ring constituted by atoms selected from the group consisting of hydrogen atoms, carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms, and a substituent on the ring is preferably constituted by atoms selected from the group consisting of hydrogen atoms, carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.

[0141] Ring L 1 and Ring L 2 The ligand composed of is preferably a ligand composed of atoms selected from the group consisting of hydrogen atoms, carbon atoms, nitrogen atoms, and oxygen atoms, and more preferably a ligand composed of hydrogen atoms, carbon atoms, and nitrogen atoms.

[0142] In formula (Z), A 1 -G 1 -A 2 Examples of the anionic bidentate ligand represented by the formula include the ligand represented by the formula below: 1 -G 1 -A 2 The anionic bidentate ligand represented by the subscript n 1 The number is different from the ligand defined by [ka] [ka] [ka] [In the formula, * indicates M 1 represents the binding site. 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, or a halogen atom, and these groups may have a substituent.

[0143] Ring L 1 The number of carbon atoms in the aromatic heterocycle represented by the following formula (I) 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. Ring L 1 Examples of the ring include a diazole ring, a triazole ring, a tetrazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, an azanaphthalene ring, and a diazanaphthalene ring, and are preferably a pyridine ring, a diazabenzene ring, an azanaphthalene ring, a diazanaphthalene ring, a triazole ring, or a diazole ring, more preferably a pyridine ring, a quinoline ring, an isoquinoline ring, a triazole ring, or a diazole ring, still more preferably a pyridine ring, a quinoline ring, or an isoquinoline ring, and particularly preferably a pyridine ring, and these rings may have a substituent.

[0144] Ring L 2 The number of carbon atoms in the aromatic hydrocarbon ring 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 in the substituent. 2Examples of the aromatic hydrocarbon ring represented by the formula (I) include a benzene ring, a naphthalene ring, an indene ring, a fluorene ring, a phenanthrene ring, a dihydrophenanthrene ring, and rings formed by condensing two to five of these rings. Since the external quantum efficiency of the light-emitting element is more excellent, a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, or a dihydrophenanthrene ring is preferred, a benzene ring, a fluorene ring, or a dihydrophenanthrene ring is more preferred, and a benzene ring is even more preferred, and these rings may have a substituent. Ring L 2 The number of carbon atoms in the aromatic heterocycle represented by the following formula (I) 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 represented by 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 fused to these rings. Since the external quantum efficiency of the light-emitting element is more excellent, 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 is preferred, 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, a dibenzofuran ring, or a dibenzothiophene ring, and these rings may have a substituent. Ring L 2 is 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, a dibenzofuran ring, or a dibenzothiophene ring, and even more preferably a benzene ring, and these rings may have a substituent.

[0145] Ring L 1 and ring L 2The substituent that may be substituted 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, an aryl group, or a monovalent heterocyclic group, and particularly preferably an aryl group or a monovalent heterocyclic group, and these groups may further have a substituent.

[0146] Ring L 1 and ring L 2 The aryl group in the substituent that may be present is preferably a phenyl group, a naphthyl group, a phenanthrenyl group, a dihydrophenantrenyl group, or a fluorenyl group, more preferably a phenyl group or a fluorenyl group, and even more preferably a phenyl group, and these groups may have a substituent. Ring L 1 and ring L 2 The monovalent heterocyclic group in the substituent that may be contained in the group 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. Ring L 1 and ring L 2 In the substituted amino group in the substituent that may be possessed by ring L, the substituent possessed by the amino group is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups may further possess a substituent. Examples and preferred ranges of the aryl group in the substituent possessed by the amino group are as follows: 1 and ring L 2 Examples and preferred ranges of the aryl group in the substituent that the amino group may have are the same as those of the ring L.1 and ring L 2 The examples and preferred range of the monovalent heterocyclic group in the substituent that may be possessed by the group are the same as those of the monovalent heterocyclic group.

[0147] Ring L 1 and ring L 2 The substituent that may be further substituted by the substituent that may be substituted by 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 an aryl group, and even more preferably an alkyl group, and these groups may further have a substituent.

[0148] Ring L 1 and ring L 2 The aryl group, monovalent heterocyclic group or substituted amino group in the substituent that may be contained in the group is preferably a group represented by formula (DA), formula (DB) or formula (DC), more preferably a group represented by formula (DA) or formula (DB), because the external quantum efficiency of the light-emitting device is more excellent.

[0149] Ring L 1 and ring L 2 At least one ring among these preferably has a group represented by formula (DA), formula (DB) or formula (DC) as a substituent, and more preferably has a group represented by formula (DA) or formula (DB) as a substituent.

[0150] [ka] [In the formula, m DA1 , m DA2 and m DA3 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. Ar DA1 , Ar DA2 and Ar DA3each independently represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. DA1 , Ar DA2 and Ar DA3 When there are multiple, 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.]

[0151] [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 Ar DA7 When there are a plurality of, 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.]

[0152] [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. DA1 When there are multiple, 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.]

[0153] m DA1 , m DA2 , m DA3 , m DA4 , m DA5 , m DA6 and 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 DA3 , m DA4 , m DA5 , m DA6 and m DA7 are preferably the same integer.

[0154] G DA is preferably an aromatic hydrocarbon group or a heterocyclic group, and more preferably a group formed by removing three hydrogen atoms directly bonded to carbon atoms or nitrogen atoms constituting a benzene ring, a pyridine ring, a pyrimidine ring, a triazine ring, or a carbazole ring, and these groups may have a substituent. G DAThe substituent that may be substituted 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 even more 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), and even more preferably a group represented by formula (GDA-11) or formula (GDA-14). [ka] [In the formula, * indicates Ar in formula (DA). DA1 or Ar in formula (DB) DA1 , Ar DA2 , or Ar DA3 Represents a bond with. ** indicates Ar in formula (DA). DA2 or Ar in formula (DB) DA2 , Ar DA4 , or Ar DA6 Represents a bond with. *** indicates Ar in formula (DA). DA3 or Ar in formula (DB) DA3 , Ar DA5 , or Ar DA7 Represents a bond with. R DA 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 If there are multiple, they may be the same or different.]

[0155] R DAis 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.

[0156] Ar DA1 , Ar DA2 , Ar DA3 , Ar DA4 , Ar DA5 , Ar DA6 and 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-5), even more preferably a group represented by formula (ArDA-1) to formula (ArDA-3), and particularly preferably a group represented by formula (ArDA-2), and these groups may have a substituent. [ka] [In the formula, R DA represents the same meaning as above. R DB 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 If there are multiple, they may be the same or different.]

[0157] 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.

[0158] Ar DA1 , Ar DA2 , Ar DA3 , Ar DA4 , Ar DA5 , Ar DA6 and Ar DA7 Examples of the substituents that may be possessed by G and the preferred range thereof are as follows: DAThe examples and preferred ranges of the substituents that may be possessed by the group are the same as those of the substituents that may be possessed by the group.

[0159] T DA is preferably a group represented by formula (TDA-1) to formula (TDA-3), more preferably a group represented by formula (TDA-1). [ka] [In the formula, R DA and R DB has the same meaning as above.]

[0160] 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) or formula (D-A3) to formula (D-A5), and even more preferably a group represented by formula (D-A1), formula (D-A3) or formula (D-A5). [ka] [In the formula, R p1 , R p2 , R p3 and 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 a plurality of, 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. Multiple np1 may be the same or different.

[0161] The group represented by formula (DB) is preferably a group represented by formula (D-B1) to formula (D-B3), and more preferably a group represented by formula (D-B1). [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 a plurality of, 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 np1s and a plurality of np2s, they may be the same or different.]

[0162] The group represented by formula (DC) is preferably a group represented by formula (D-C1) to formula (D-C4), more preferably a group represented by formula (D-C1) to formula (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). [ka] [In the formula, R p4 , R p5 and R p6 R each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or a halogen atom. p4 , R p5 and R p6 When there are a plurality of, 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.

[0163] np1 is preferably an integer of 0 to 2, more 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, more preferably 0. np5 is preferably an integer of 0 to 3, more preferably 0 or 1. np6 is preferably an integer of 0 to 2, more preferably 0 or 1.

[0164] R p1 , R p2 , R p3 , R p4 , R p5 and R p6 The alkyl group or cycloalkyl group in is 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.

[0165] R p1 , R p2 , R p3 , R p4 , R p5 and R p6 The alkoxy group or cycloalkoxy group in the formula (I) is preferably a methoxy group, a 2-ethylhexyloxy group, or a cyclohexyloxy group.

[0166] R p1 , R p2 , R p3 , R p4 , R p5 and R p6 is preferably an alkyl group which may have a substituent or a cycloalkyl group which may have a substituent, more preferably an alkyl group which may have a substituent, 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.

[0167] Ring L 1 When there are a plurality of substituents that may be possessed by ring L, it is preferred that they are not bonded to each other to form a ring together with the atoms to which they are bonded. 2 When there are a plurality of substituents that may be possessed by ring L, it is preferred that they are not bonded to each other to form a ring together with the atoms to which they are bonded. 1 and the substituents which may be present on ring L 2 It is preferred that the substituents which may be possessed by the group do not bond to each other to form a ring together with the atoms to which they are bonded.

[0168] The metal complex represented by formula (Z) is preferably a metal complex represented by formula (Z-1) because the external quantum efficiency of the light-emitting device is superior. [ka]

[0169] M 1 , n 1 , n 2 , E 1 and A 1 -G 1 -A 2 represents the same meaning as above. Ring L 1A represents a 5- or 6-membered aromatic heterocycle. Ring L 1A is preferably a pyridine ring, a diazabenzene ring, an azanaphthalene ring, a diazanaphthalene ring, a triazole ring, or a diazole ring, since the external quantum efficiency of the light-emitting element is more excellent, more preferably a pyridine ring, a quinoline ring, an isoquinoline ring, a triazole ring, or a diazole ring, even more preferably a pyridine ring, a quinoline ring, or an isoquinoline ring, and particularly preferably a pyridine ring, and these rings may have a substituent. Ring L 1A Examples of the substituents that may be possessed by ring L and the preferred range thereof are as follows: 1 and ring L 2 The examples and preferred ranges of the substituents that may be possessed by the group are the same as those of the substituents that may be possessed by the group. Ring L 1A When there are a plurality of substituents that may be possessed by the group, it is preferred that they are not bonded to each other (do not form a ring).

[0170] 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 there are multiple E's, they may be the same or different. 21AIf is a nitrogen atom, R 21A does not exist. E 22A If is a nitrogen atom, R 22A does not exist. E 23A If is a nitrogen atom, R 23A does not exist. E 24A If 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 there are multiple R, 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 and 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.

[0171] The metal complex represented by formula (Z-1) is preferably a metal complex represented by formula (1-Z1) to formula (1-Z10), more preferably a metal complex represented by formula (1-Z6) to formula (1-Z10), and even more preferably a metal complex represented by formula (1-Z6). [ka] [ka] [In the formula, M 1 , n 1, n 2 , R 11A , R 12A , R 13A , R 21A , R 22A , R 23A , R 24A and A 1 -G 1 -A 2 has the same meaning as above.]

[0172] R 11B , R 12B , R 13B , R 14B , R 15B , R 16B , R 17B and R 18B is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, since this results in a more excellent external quantum efficiency of the light-emitting element, and is more preferably a hydrogen atom, an aryl group, a monovalent heterocyclic group, or a substituted amino group, and these groups may have a substituent.

[0173] In formula (1-Z1), formula (1-Z3), formula (1-Z4) and formula (1-Z5), R 11A 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. In formula (1-Z3) and formula (1-Z4), R 12A is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, more preferably a hydrogen atom, an alkyl group, or an aryl group, even more preferably a hydrogen atom or an alkyl group, and particularly preferably a tertiary alkyl group, and these groups may have a substituent.

[0174] In formula (1-Z2) and formula (1-Z5), R 12Ais 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. In formula (1-Z5), R 11A is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, more preferably a hydrogen atom, an alkyl group, or an aryl group, and even more preferably a hydrogen atom, and these groups may have a substituent.

[0175] In formula (1-Z1), formula (1-Z2), formula (1-Z4) and formula (1-Z5), R 13A is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, more preferably a hydrogen atom, an alkyl group, or an aryl group, and even more preferably an aryl group, and these groups may have a substituent.

[0176] R 11A ~R 13A Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in 1 and ring L 2 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. R 11A ~R 13A Examples of the substituents that may be possessed by ring L and the preferred range thereof are as follows: 1 and ring L 2 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.

[0177] In formulas (1-Z1) to (1-Z4), R 11A and R 12A , R 12A and R 13A , and R 11A and R 21A are preferably not bonded to each other (do not form a ring).

[0178] In formula (1-Z6), 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 they are 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 12B , R 12B and R 13B , R 11B and R 21A , 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 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 they are bonded. 11B and R 12B , R12B 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. R 11B ~R 18B is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, since this results in a more excellent external quantum efficiency of the light-emitting element, and is more preferably a hydrogen atom, an aryl group, a monovalent heterocyclic group, or a substituted amino group, and these groups may have a substituent.

[0179] R 11B and R 14B ~R 18B is preferably a hydrogen atom since this facilitates the synthesis of the metal complex, and these groups may have a substituent. R 12B is preferably a hydrogen atom, and these groups may have a substituent. R 13B is preferably a group represented by a hydrogen atom, and these groups may have a substituent.

[0180] R 11B ~R 18B Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in 1 and ring L 2 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. R 11B ~R 18B Examples of the substituents that may be possessed by ring L and the preferred range thereof are as follows: 1 and ring L 2 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.

[0181] In formulas (1-Z6) to (1-Z10), R 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 , R 18B and R 21A , R 11B and R 18B , R 14B and R 15B , and R 12B and R 18B are preferably not bonded to each other to form a ring together with the atoms to which they are attached.

[0182] The metal complex represented by formula (Z) has excellent external quantum efficiency of the light-emitting device, and therefore is preferably a metal complex represented by formula (1-Z2), formula (1-Z3), or formula (1-Z6), and more preferably a metal complex represented by formula (1-Z6).

[0183] Examples of the metal complex represented by formula (Z) include metal complexes represented by formulae (Ir-1) to (Ir-34). [ka] [ka] [ka] [ka] [In the formula, Z 1represents a group represented by formula (DA), formula (DB) or formula (DC). 1 may be the same or different. R L5 R is an alkyl group, a cycloalkyl group, a halogen atom, an aryl group, a 1,3,5-triazinyl group having aryl groups as substituents at the 2- and 4-positions, a group represented by formula (DA), a group represented by formula (DB), or a group represented by formula (DC). L5 When there are multiple groups, they may be the same or different.

[0184] In formulas (Ir-1) to (Ir-34), R L5 is preferably a group represented by any one of formulae (II-01) to (II-22) in Group II.

[0185] <Group II> [ka]

[0186] [ka]

[0187] [ka]

[0188] In formulas (Ir-1) to (Ir-34), R L5 is preferably a group represented by any one of formulas (II-16) to (II-22).

[0189] Examples of the metal complex represented by formula (Z) include metal complexes represented by formulae (Ir-35) to (Ir-43).

[0190] [ka] [ka] [ka] [In the formula, Z 2 represents a group represented by formula (DA), formula (DB) or formula (DC). 2 may be the same or different. R L6 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. L6 may be the same or different. R L7 represents an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. L7 may be the same or different.]

[0191] Examples of the metal complex represented by formula (Z) include metal complexes represented by the following formula:

[0192] [ka]

[0193] [ka]

[0194] [ka]

[0195] [ka]

[0196] [ka]

[0197] Phosphorescent transition metal complexes are available from Aldrich, Luminescence Technology Corp., American Dye Source, and others. It can also be produced by known methods described in documents such as "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, WO 2006 / 121811, JP-A-2013-147450, and JP-A-2014-224101.

[0198] In the present disclosure, one type of metal complex may be used alone, or two or more types may be used in combination.

[0199] The metal complex represented by formula (Z) may have multiple geometric isomers, and any geometric isomer may be used. However, since the external quantum efficiency of the light-emitting device is improved, the facial isomer is preferably 80 mol % or more, more preferably 90 mol % or more, even more preferably 99 mol % or more, and particularly preferably 100 mol % of the total metal complex.

[0200] <Metal Complex Manufacturing Method> ·Manufacturing method 1 The metal complex can be produced, for example, by reacting a compound serving as a ligand with a metal compound. If necessary, a functional group conversion reaction of the ligand of the metal complex may be carried out.

[0201] The compound represented by formula (Z) can be prepared, for example, by reacting a compound represented by formula (MM-1) with an iridium compound or a hydrate thereof in step A, and reacting a metal complex represented by formula (MM-2) with a compound represented by formula (MM-1) or A1 -G 1 -A 2 and (B) reacting a precursor of a ligand represented by the formula (I) with a precursor of a ligand represented by the formula (I).

[0202] [ka] [In the formula, E 1 , E 2 , ring L 1 , ring L 2 and M 1 has the same meaning as above.]

[0203] In step A, examples of iridium compounds include iridium chloride, tris(acetylacetonato)iridium(III), chloro(cyclooctadiene)iridium(I) dimer, and iridium(III) acetate. Examples of hydrates of iridium compounds include iridium chloride trihydrate.

[0204] Step A and Step B are usually carried out in a solvent. Examples of the solvent include alcoholic solvents such as methanol, ethanol, propanol, ethylene glycol, glycerin, 2-methoxyethanol, and 2-ethoxyethanol; etheric solvents such as diethyl ether, tetrahydrofuran (THF), dioxane, cyclopentyl methyl ether, and diglyme; halogenated solvents such as methylene chloride and chloroform; nitrile solvents such as acetonitrile and benzonitrile; hydrocarbon solvents such as hexane, decalin, toluene, xylene, and mesitylene; amide solvents such as N,N-dimethylformamide and N,N-dimethylacetamide; acetone, dimethyl sulfoxide, and water.

[0205] In Step A and Step B, the reaction time is usually 30 minutes to 150 hours, and the reaction temperature is usually between the melting point and the boiling point of the solvent present in the reaction system.

[0206] In step A, the compound represented by formula (MM-1) is usually used in an amount of 2 to 20 moles per mole of the iridium compound or a hydrate thereof.

[0207] In step B, a compound represented by formula (MM-1) or A 1 -G 1 -A 2 The amount of the precursor of the ligand represented by formula (MM-2) is usually 1 to 100 moles per mole of the metal complex represented by formula (MM-2).

[0208] In step B, the reaction is preferably carried out in the presence of a silver compound such as silver trifluoromethanesulfonate. When a silver compound is used, the amount thereof is usually 2 to 20 moles per mole of the metal complex represented by formula (MM-2).

[0209] The compound represented by formula (MM-1) can be synthesized, for example, by a coupling reaction such as Suzuki reaction, Kumada reaction, Stille reaction, or Negishi reaction between a compound represented by formula (MM-3) and a compound represented by formula (9).

[0210] [ka] [In the formula, E 1 , E 2 , ring L 1 and ring L 2 represents the same meaning as above. W 1 and W 2 are each independently -B(OR W1 )2, an alkylsulfonyloxy group, a cycloalkylsulfonyloxy group, an arylsulfonyloxy group, a chlorine atom, a bromine atom, or an iodine atom, and these groups may have a substituent. W1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or an amino group, and these groups may have a substituent. W1may be the same or different and may be bonded to each other to form a ring structure together with the oxygen atom to which they are bonded.

[0211] -B(OR W1 Examples of the group represented by formula (W-2) include groups represented by formula (W-1) to formula (W-10).

[0212] [ka]

[0213] W 1 and W 2 Examples of the alkylsulfonyloxy group represented by the formula (I) include a methanesulfonyloxy group, an ethanesulfonyloxy group, and a trifluoromethanesulfonyloxy group. 1 and W 2 Examples of the arylsulfonyloxy group represented by the following formula include a p-toluenesulfonyloxy group.

[0214] W 1 and W 2 is preferably -B(OR W1 )2, a trifluoromethanesulfonyloxy group, a bromine atom or an iodine atom, and more preferably a group represented by formula (W-7).

[0215] These reactions are usually carried out in a solvent. The solvent, reaction time and reaction temperature are the same as those described in Step A and Step B. In these reactions, the amount of the compound represented by formula (9) is usually 0.05 to 20 moles per mole of the compound represented by formula (MM-3).

[0216] In the coupling reaction, a catalyst such as a palladium catalyst may be used to promote the reaction, such as palladium acetate, bis(triphenylphosphine)palladium(II) dichloride, tetrakis(triphenylphosphine)palladium(0), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), or tris(dibenzylideneacetone)dipalladium(0). The palladium catalyst may be used in combination with a phosphorus compound such as triphenylphosphine, tri(o-tolyl)phosphine, tri(tert-butyl)phosphine, tricyclohexylphosphine, or 1,1'-bis(diphenylphosphino)ferrocene.

[0217] When a palladium catalyst is used in the coupling reaction, the amount thereof is usually an effective amount, for example, per 1 mole of the compound represented by formula (MM-3), and preferably 0.00001 to 10 moles in terms of elemental palladium. In the coupling reaction, a base is used in combination, if necessary.

[0218] The compounds, catalysts and solvents used in the reactions explained in <Method for producing metal complexes> may each be used alone or in combination of two or more.

[0219] The amount of the polymer compound in the composition of the present disclosure is preferably 1 to 90 mass %, more preferably 10 to 70 mass %, and even more preferably 30 to 70 mass %, based on the total amount of the composition, since this results in excellent external quantum efficiency of the light-emitting device.

[0220] The content of the metal complex in the composition of the present disclosure is preferably 1 to 70 mass %, more preferably 10 to 60 mass %, and even more preferably 15 to 50 mass %, based on the total amount of the composition.

[0221] When the composition of the present disclosure contains a metal complex, efficient energy transfer from the metal complex to the first structural unit present in the composition can be achieved, thereby realizing a light-emitting device with even more excellent external quantum efficiency. P (eV), the value of the energy level of the lowest triplet excited state of the polymer compound of the present disclosure is T F (eV), T P and T F It is preferable that formula (A) is satisfied, since the external quantum efficiency of the light-emitting device is excellent. |T P |≧|T F |···(A)

[0222] The value of the energy level of the lowest singlet excited state of the polymer compound of the present disclosure is S F (eV), T P and S F It is preferable that formula (B) is satisfied, since the external quantum efficiency of the light-emitting device is excellent. |T P |≧|S F |···(B)

[0223] Examples of the composition of the present disclosure include the compositions shown in Table 2.

[0224] [Table 2] [In the table, t', u', and v' represent the mass ratio of each component. t'+u'+v'=100, and 50≦t'+u'≦100. The other components refer to components other than the polymer compound and metal complex of the present disclosure. The other components may be low-molecular-weight compounds or polymer compounds, and may be one type or two or more types.]

[0225] The composition of the present disclosure may further contain 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.

[0226] [Hole transport material] Hole transport materials are classified into low molecular weight compounds and high molecular weight compounds, with high molecular weight compounds being preferred. The hole transport material is more preferably a compound having a crosslinking group (crosslinking material). The crosslinking material is preferably a low molecular weight compound having at least one crosslinking group selected from the above-mentioned Group A of crosslinking groups, or a high molecular weight compound containing a crosslinking structural unit having at least one crosslinking group selected from the above-mentioned Group A of crosslinking groups.

[0227] Examples of the polymer compound include polyvinylcarbazole and its derivatives, and polyarylene and its derivatives having an aromatic amine structure in the side chain or main chain. The polymer compound may be a compound to which an electron-accepting moiety is bonded. Examples of the electron-accepting moiety include fullerene, tetrafluorotetracyanoquinodimethane, tetracyanoethylene, and trinitrofluorenone, with fullerene being preferred.

[0228] In the composition of the present disclosure, the blending amount of the hole transport material is usually 1 to 400 parts by mass, and preferably 5 to 150 parts by mass, per 100 parts by mass of the total amount of the polymer compound and metal complex in the composition.

[0229] The hole transport material may be used alone or in combination of two or more kinds.

[0230] [Electron transport material] Electron transport materials are classified into low molecular weight compounds and high molecular weight compounds. The electron transport material may have a crosslinking group.

[0231] Examples of low molecular weight compounds include metal complexes with 8-hydroxyquinoline as a ligand, oxadiazole, anthraquinodimethane, benzoquinone, naphthoquinone, anthraquinone, tetracyanoanthraquinodimethane, fluorenone, diphenyldicyanoethylene, and diphenoquinone, as well as derivatives thereof.

[0232] Examples of the polymer compound include polyphenylene, polyfluorene, and derivatives thereof. The polymer compound may be doped with a metal.

[0233] In the composition of the present disclosure, the amount of the electron transport material is usually 1 to 400 parts by mass, and preferably 5 to 150 parts by mass, per 100 parts by mass of the total amount of the polymer compound and metal complex in the composition.

[0234] The electron transporting materials may be used alone or in combination of two or more.

[0235] [Hole injection material and electron injection material] The hole injection material and the electron injection material are each classified into a low molecular weight compound and a high molecular weight compound. The hole injection material and the electron injection material may have a crosslinking group.

[0236] 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.

[0237] Examples of polymer compounds 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.

[0238] In the composition of the present disclosure, the blending 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 total amount of the polymer compound and the metal complex in the composition.

[0239] The hole injection material and the electron injection material may each be used alone or in combination of two or more kinds.

[0240] [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.

[0241] The type of ion to be doped is an anion for a hole injection material, or a cation for an electron injection material. Examples of anions include polystyrene sulfonate ions, alkylbenzene sulfonate ions, and camphor sulfonate ions. Examples of cations include lithium ions, sodium ions, potassium ions, and tetrabutylammonium ions.

[0242] The doping ions may be of one kind or two or more kinds.

[0243] [Luminescent materials] A luminescent material is a material that emits light when exposed to external energy, and may be a material that emits light itself or a material that causes other materials to emit light. Light-emitting materials are classified into low molecular weight compounds and high molecular weight compounds. The light-emitting material may have a crosslinking group.

[0244] Examples of low molecular weight compounds include fluorene and derivatives thereof, phenylene and derivatives thereof, phenanthrene and derivatives thereof, carbazole and derivatives thereof, naphthalene and derivatives thereof, anthracene and derivatives thereof, perylene and derivatives thereof, and triplet luminescent complexes having iridium, platinum, or europium as a central metal.

[0245] 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 carbazolediyl group, a phenoxazinediyl group, a phenothiazinediyl group, an anthracenediyl group, a pyrenediyl group, and the like.

[0246] The light-emitting material may include a low molecular weight compound and a high molecular weight compound, and preferably includes a triplet light-emitting complex and a high molecular weight compound.

[0247] In the composition of the present disclosure, the content of the light-emitting material is usually 0.1 to 400 parts by mass per 100 parts by mass of the total amount of the polymer compound and the metal complex in the composition.

[0248] [Antioxidants] The antioxidant may be any compound that is soluble in the same solvent as the polymer compound of the present disclosure and does not inhibit light emission and charge transport, and examples thereof include phenol-based antioxidants and phosphorus-based antioxidants.

[0249] In the composition of the present disclosure, the blending amount of the antioxidant is usually 0.001 to 10 parts by mass per 100 parts by mass of the total amount of the polymer compound and metal complex in the composition.

[0250] The antioxidants may be used alone or in combination of two or more.

[0251] <Ink> The composition of the present disclosure may contain a solvent, and hereinafter, a composition containing a solvent will be referred to as an "ink."

[0252] The ink of the present disclosure can be suitably used in coating methods such as 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, and nozzle coating.

[0253] The viscosity of the ink of the present disclosure may be adjusted depending on the type of application 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 mPa·s to 30 mPa·s at 25°C, since clogging and deflection during discharge are less likely to occur.

[0254] The solvent contained in the ink of the present disclosure is preferably a solvent that can dissolve or uniformly disperse 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. 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 and cyclohexanol, and the like; sulfoxide solvents such as dimethyl sulfoxide, and the like; and amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide, and the like. The solvents may be used alone or in combination of two or more.

[0255] In the ink of the present disclosure, the blending amount of the solvent 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 total amount of the polymer compound and metal complex in the composition.

[0256] <Membrane> The film contains the composition of the present disclosure.

[0257] The film is suitable as a light-emitting layer in a light-emitting device.

[0258] The film can be produced using 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.

[0259] The thickness of the film is usually 1 nm to 10 μm.

[0260] <Light-emitting element> The light-emitting device of the present disclosure is a light-emitting device containing the polymer compound of the present disclosure. The light-emitting element of the present disclosure has, for example, an anode, a cathode, and an organic layer provided between the anode and the cathode and containing the polymer compound of the present disclosure.

[0261] [Layer composition] The layer containing the composition of the present disclosure is typically one or more 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 light-emitting layer. These layers each contain a light-emitting material, a hole-transporting material, a hole-injecting material, an electron-transporting material, and an electron-injecting material. These layers can be formed using the same method as for producing the above-described film 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-described solvent to prepare an ink.

[0262] The light-emitting element has a light-emitting layer between an anode and a cathode. From the viewpoint of hole injection and hole transport properties, the light-emitting element of the present disclosure preferably has at least one hole injection layer and hole transport layer between the anode and the light-emitting layer, and from the viewpoint of electron injection and electron transport properties, preferably has at least one electron injection layer and electron transport layer between the cathode and the light-emitting layer.

[0263] Examples of materials for the hole transport layer, electron transport layer, light-emitting layer, hole injection layer, and electron injection layer include the composition of the present disclosure as well as the hole transport material, electron transport material, light-emitting material, hole injection material, and electron injection material described above, respectively.

[0264] When the materials for the hole transport layer, electron transport layer, and light-emitting layer are soluble in a solvent used to form the hole transport layer, electron transport layer, and layer adjacent to the light-emitting layer in the fabrication of a light-emitting device, the materials preferably have a crosslinking group to prevent the materials from dissolving in the solvent. After forming each layer using a material having a crosslinking group, the layer can be made insoluble by crosslinking the crosslinking group.

[0265] In the light-emitting element of the present disclosure, examples of methods 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, vacuum deposition from powder and film formation from a solution or molten state; and when a high-molecular-weight compound is used, examples of methods for forming a film from a solution or molten state.

[0266] The order, number and thickness of the layers to be stacked are adjusted taking into consideration the external quantum efficiency and luminance life.

[0267] [Substrate / Electrode] The substrate in the light-emitting element may be any substrate on which electrodes can be formed and which is not chemically changed when an organic layer is formed, such as a substrate made of a material such as glass, plastic, silicon, etc. In the case of an opaque substrate, it is preferable that the electrode farthest from the substrate is transparent or translucent.

[0268] Examples of materials for the anode include conductive metal oxides and translucent metals, and preferred are indium oxide, zinc oxide, and tin oxide; conductive compounds such as indium tin oxide (ITO) and indium zinc oxide; silver-palladium-copper composite (APC); NESA, gold, platinum, silver, and copper.

[0269] Cathode materials include, for example, metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, zinc, and indium; alloys of two or more of these; alloys of one or more of these with one or more of silver, copper, manganese, titanium, cobalt, nickel, tungsten, and tin; and graphite and graphite intercalation compounds. Examples of alloys include magnesium-silver alloy, magnesium-indium alloy, magnesium-aluminum alloy, indium-silver alloy, lithium-aluminum alloy, lithium-magnesium alloy, lithium-indium alloy, and calcium-aluminum alloy. The anode and cathode may each have a laminated structure of two or more layers.

[0270] [Application] The light-emitting device of the present disclosure is useful for displays, lighting, and the like.

[0271] Although a preferred embodiment of the present disclosure has been described above, the present disclosure is not limited to the above embodiment.

[0272] The present disclosure may also relate to a method for producing a polymer compound.

[0273] <Method of manufacturing polymer compounds> In one embodiment, a method for producing a polymer compound according to the present disclosure includes a step of polymerizing a compound having a polymerizable group in the presence of a transition metal catalyst and an inorganic base, and the compound having a polymerizable group has two or more boron atoms, a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, and sp 3 The method may also include a fused ring compound having a fused heterocyclic skeleton containing at least one selected from the group consisting of carbon atoms and a polymerizable group, wherein the fused heterocyclic skeleton satisfies at least one of requirement (i) and requirement (ii). (i) A nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, and the sp 1 atom contained in the ring of the fused heterocyclic skeleton 3 The total number of carbon atoms is 4 or more. (ii) The number of nitrogen atoms contained in the ring of the fused heterocyclic skeleton is two or more.

[0274] (Fused ring compound having a fused heterocyclic skeleton and a polymerizable group) The number of carbon atoms contained in the ring of the fused heterocyclic skeleton, not including the number of carbon atoms of the substituent, is usually 1 to 500, may be 1 to 300, or may be 5 to 100, and is preferably 10 to 90, more preferably 15 to 80, still more preferably 20 to 70, particularly preferably 25 to 60, and particularly preferably 30 to 50, since this provides a more excellent external quantum efficiency of the light-emitting device. The number of heteroatoms contained in the ring of the fused heterocyclic skeleton, not including the number of heteroatoms of the substituent, is usually 2 to 50, may be 2 to 40, or may be 2 to 30, and is preferably 3 to 25, more preferably 4 to 20, even more preferably 5 to 15, and particularly preferably 6 to 10, since this provides a more excellent external quantum efficiency of the light-emitting device. The number of boron atoms contained in the ring of the fused heterocyclic skeleton, not including the number of boron atoms in the substituent, is usually 2 to 20, and may be 2 to 15. In order to improve the external quantum efficiency of the light-emitting device, the number is preferably 2 to 10, more preferably 2 to 7, even more preferably 2 to 5, and particularly preferably 2 or 3.

[0275] Nitrogen atoms, oxygen atoms, sulfur atoms, selenium atoms and sp atoms contained in the ring of the fused heterocyclic skeleton 3 The total number of carbon atoms, not including the number of atoms of the substituents, is 1 or more (however, when the fused heterocyclic skeleton satisfies the requirement (i), it is 4 or more. When the fused heterocyclic skeleton satisfies the requirement (ii), it is 2 or more). Since the external quantum efficiency of the light-emitting device is more excellent, it is preferably 2 or more, more preferably 3 or more, and particularly preferably 4 or more. In addition, the nitrogen atom, oxygen atom, sulfur atom, selenium atom, and sp atom contained in the ring of the fused heterocyclic skeleton are preferably 2 or more, more preferably 3 or more, and particularly preferably 4 or more. 3The total number of carbon atoms, not including the number of substituent atoms, is usually 30 or less, may be 25 or less, or may be 20 or less, and is preferably 15 or less, more preferably 10 or less, even more preferably 8 or less, particularly preferably 6 or less, and especially preferably 4 or less, since this results in better external quantum efficiency of the light-emitting element.

[0276] When the fused heterocyclic skeleton contains a nitrogen atom in the ring, the number of nitrogen atoms contained in the ring of the heterocyclic skeleton, not including the number of nitrogen atoms of substituents, is 1 or more (however, when the fused heterocyclic skeleton satisfies requirement (ii), the number is 2 or more), and since the external quantum efficiency of the light-emitting device is more excellent, the number is preferably 2 or more, more preferably 3 or more, and even more preferably 4 or more. Furthermore, when the heterocyclic skeleton contains a nitrogen atom in the ring, the number of nitrogen atoms contained in the ring of the fused heterocyclic skeleton, not including the number of nitrogen atoms of substituents, is usually 30 or less, and may be 25 or less, or may be 20 or less; since the external quantum efficiency of the light-emitting device is more excellent, the number is preferably 15 or less, more preferably 10 or less, even more preferably 8 or less, particularly preferably 6 or less, and especially preferably 4 or less.

[0277] When the fused heterocyclic skeleton contains a nitrogen atom in the ring, the external quantum efficiency of the light-emitting device is better, so it is preferable that at least one of the nitrogen atoms contained in the fused heterocyclic skeleton is a nitrogen atom that does not form a double bond, and it is more preferable that all of the nitrogen atoms contained in the heterocyclic skeleton are nitrogen atoms that do not form a double bond.

[0278] When the fused heterocyclic skeleton contains a nitrogen atom in the ring, the number of nitrogen atoms not forming a double bond contained in the ring of the fused heterocyclic skeleton, not including the number of nitrogen atoms not forming a double bond of the substituent, is 1 or more (however, when the fused heterocyclic skeleton satisfies requirement (ii), the number is 2 or more), and since the external quantum efficiency of the light-emitting device is more excellent, the number is preferably 2 or more, more preferably 3 or more, and even more preferably 4 or more. Furthermore, when the fused heterocyclic skeleton contains a nitrogen atom in the ring, the number of nitrogen atoms not forming a double bond contained in the ring of the fused heterocyclic skeleton, not including the number of nitrogen atoms not forming a double bond of the substituent, is usually 30 or less, may be 25 or less, or may be 20 or less; since the external quantum efficiency of the light-emitting device is more excellent, the number is preferably 15 or less, more preferably 10 or less, even more preferably 8 or less, particularly preferably 6 or less, and especially preferably 4 or less.

[0279] The fused heterocyclic skeleton preferably contains a boron atom and at least one atom selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, and a selenium atom in the ring, because the external quantum efficiency of the light-emitting device is superior; more preferably contains a boron atom and at least one atom selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom in the ring; still more preferably contains a boron atom and at least one atom selected from the group consisting of a nitrogen atom and an oxygen atom in the ring; particularly preferably contains a boron atom and a nitrogen atom in the ring; and especially preferably contains a nitrogen atom that does not form a double bond with the boron atom in the ring.

[0280] The number of rings constituting the fused rings of the fused heterocyclic skeleton is preferably 7 or more, more preferably 8 or more, and even more preferably 9 or more, since the external quantum efficiency of the light-emitting device is better. The number of rings constituting the fused rings of the fused heterocyclic skeleton is usually 60 or less, and since the external quantum efficiency of the light-emitting device is better, the number is preferably 40 or less, more preferably 30 or less, even more preferably 25 or less, particularly preferably 20 or less, especially preferably 15 or less, and especially more preferably 13 or less. The compound having a fused heterocyclic skeleton can also be referred to as a compound having a heterocyclic group (b) containing a fused heterocyclic skeleton.

[0281] The heterocyclic group (b) is a heterocyclic group consisting of two or more boron atoms and a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, and a sp 3 The heterocyclic group may be a group in which one or more hydrogen atoms directly bonded to atoms constituting the ring have been removed from a fused heterocyclic skeleton containing at least one kind selected from the group consisting of carbon atoms in the ring, and the group may have a substituent.

[0282] The substituent that the heterocyclic group (b) may have is preferably a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, because this provides a light-emitting device with better external quantum efficiency; more preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, or a substituted amino group; even more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group; and particularly preferably an alkyl group, a cycloalkyl group, an aryl group, or a substituted amino group, and these groups may further have a substituent.

[0283] The aryl group in the substituent that the heterocyclic group (b) may have is preferably a group in which one hydrogen atom directly bonded to an atom constituting the ring has been removed from a monocyclic or bicyclic to hexacyclic aromatic hydrocarbon ring, since this provides a light-emitting device with better external quantum efficiency; more preferably a group in which one hydrogen atom directly bonded to an atom constituting the ring has been removed from a monocyclic, bicyclic or tricyclic aromatic hydrocarbon ring; even more preferably a group in which one hydrogen atom directly bonded to an atom constituting the ring has been removed from a monocyclic or tricyclic aromatic hydrocarbon ring; and particularly preferably a group in which one hydrogen atom directly bonded to an atom constituting the ring has been removed from a monocyclic aromatic hydrocarbon ring; and these groups may further have a substituent.

[0284] The aryl group in the substituent that the heterocyclic group (b) may have is preferably a group in which one hydrogen atom directly bonded to an atom constituting the ring has been removed from benzene, naphthalene, indene, anthracene, phenanthrene, dihydrophenanthrene, or fluorene, because this further improves the external quantum efficiency of the light-emitting device; more preferably, a group in which one hydrogen atom directly bonded to an atom constituting the ring has been removed from benzene, naphthalene, anthracene, phenanthrene, or fluorene; even more preferably, a group in which one hydrogen atom directly bonded to an atom constituting the ring has been removed from benzene or fluorene; and particularly preferably, a phenyl group, and these groups may have a substituent. The aryl group in the substituent that the heterocyclic group (b) may have may be an aryl group having three or more substituents as described below.

[0285] The monovalent heterocyclic group in the substituent that the heterocyclic group (b) may have is preferably a group in which one hydrogen atom directly bonded to an atom constituting the ring has been removed from a monocyclic or bicyclic to hexacyclic heterocycle, more preferably a group in which one hydrogen atom directly bonded to an atom constituting the ring has been removed from a monocyclic, bicyclic or tricyclic heterocycle, even more preferably a group in which one hydrogen atom directly bonded to an atom constituting the ring has been removed from a monocyclic or tricyclic heterocycle, and particularly preferably a group in which one hydrogen atom directly bonded to an atom constituting the ring has been removed from a tricyclic heterocycle, and these groups may have a substituent, because the external quantum efficiency of the light-emitting device is more excellent.

[0286] The monovalent heterocyclic group in the substituent that the heterocyclic group (b) may have is preferably a group in which one hydrogen atom directly bonded to an atom constituting the ring has been removed from furan, thiophene, pyrrole, diazole, triazole, pyridine, diazabenzene, triazine, benzofuran, benzothiophene, indole, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, phenoxazine, phenothiazine, 9,10-dihydroacridine, 5,10-dihydrophenazine, acridone, azaanthracene, diazaanthracene, azaphenanthrene, or diazaphenanthrene, because this further improves the external quantum efficiency of the light-emitting device, and more preferably pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene,

[0033] The group is preferably a group obtained by removing one hydrogen atom directly bonded to an atom constituting the ring from pyridine, diazabenzene, triazine, carbazole, phenoxazine, phenothiazine, 9,10-dihydroacridine, or 5,10-dihydrophenazine, and more preferably a group obtained by removing one hydrogen atom directly bonded to an atom constituting the ring from pyridine, diazabenzene, triazine, carbazole, phenoxazine, phenothiazine, 9,10-dihydroacridine, or 5,10-dihydrophenazine, and particularly preferably a group obtained by removing one hydrogen atom directly bonded to an atom constituting the ring from carbazole, and particularly preferably a group obtained by removing one hydrogen atom directly bonded to an atom constituting the ring from carbazole, and these groups may have a substituent. The monovalent heterocyclic group in the substituent that the heterocyclic group (b) may have may be a monovalent heterocyclic group having three or more substituents as described below.

[0287] In the substituted amino group in the substituent that the heterocyclic group (b) may have, the substituent that the amino group has 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 that the amino group has are the same as the examples and preferred ranges of the aryl group and the monovalent heterocyclic group in the substituent that the heterocyclic group (b') may have, respectively, which will be described later.

[0288] The substituent that the heterocyclic group (b) may have further may be, in order to improve the external quantum efficiency of the light-emitting device, preferably a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, even more preferably an alkyl group, a cycloalkyl group, or an aryl group, and particularly preferably an alkyl group or a cycloalkyl group. These groups may have further substituents, but preferably do not have further substituents. Examples and preferred ranges of the aryl group, monovalent heterocyclic group, and substituted amino group in the substituent that the heterocyclic group (b) may further have are the same as the examples and preferred ranges of the aryl group, monovalent heterocyclic group, and substituted amino group in the substituent that the heterocyclic group (b') may have.

[0289] The term "nitrogen atom not forming a double bond" means a nitrogen atom that is bonded to three other atoms via single bonds. "Containing a nitrogen atom not forming a double bond in the ring" means that -N(R N )-(wherein, R N represents a hydrogen atom or a substituent.) or the formula:

[0290] [ka] This means that the compound contains a group represented by the formula: R N Examples and preferred ranges of R xb The examples and preferred ranges are the same as those of the above.

[0291] A heterocyclic skeleton preferably satisfies at least one of requirement (i) and requirement (ii), and more preferably satisfies both requirements (i) and (ii), because the external quantum efficiency of the light-emitting device is superior in such a case.

[0292] The fused ring compound is preferably a thermally activated delayed fluorescence (TADF) compound, since it provides a light-emitting device with superior external quantum efficiency.

[0293] ΔE of fused ring compounds ST For example, the ΔE of compound (B) may be 2.0 eV or less, 1.5 eV or less, 1.0 eV or less, 0.80 eV or less, 0.60 eV or less, or 0.55 eV or less, but since the external quantum efficiency of the light-emitting device is better, it is preferably 0.50 eV or less, more preferably 0.45 eV or less, even more preferably 0.40 eV or less, particularly preferably 0.37 eV or less, especially preferably 0.35 eV or less, especially more preferably 0.33 eV or less, especially more preferably 0.32 eV or less, and especially especially preferably 0.30 eV or less. ST may be, for example, 0.001 eV or more, 0.01 eV or more, 0.10 eV or more, 0.15 eV or more, 0.20 eV or more, or 0.25 eV or more.

[0294] The molecular weight of fused ring compounds is usually 1×10 2 That's 2 x 10 2 May be greater than 3 x 10 2 May be more than 4 x 10 2 or more, and is preferably 5×10 because the external quantum efficiency of the light-emitting device is better. 2 More preferably, it is 6×102 More preferably, 8×10 2 More preferably, it is 1.0×10 2 More preferably, it is 1.2×10 3 More preferably, it is 1.4×10 or more. 3 The molecular weight of the fused ring compound is usually 1×10 4 The external quantum efficiency of the light-emitting device is excellent, and the fused ring compound is easily synthesized. Therefore, it is preferably 8 × 10 3 or less, more preferably 6×10 3 or less, and more preferably 4×10 3 It is particularly preferably 2 × 10 3 The following is the result.

[0295] sp in fused ring compounds 3 The total number of carbon atoms may be, for example, 1 or more, 3 or more, or 5 or more, and is preferably 7 or more, more preferably 9 or more, even more preferably 10 or more, particularly preferably 15 or more, especially preferably 20 or more, and especially preferably 25 or more, since the external quantum efficiency of the light-emitting device is more excellent. 3 The total number of carbon atoms may be, for example, 1000 or less, 800 or less, 600 or less, 400 or less, or 200 or less, and is preferably 100 or less, more preferably 70 or less, even more preferably 50 or less, and particularly preferably 30 or less, since this provides a better external quantum efficiency of the light-emitting element and makes it easier to synthesize the fused ring compound.

[0296] The fused ring compound may have at least one selected from the group consisting of an aryl group having three or more substituents and a monovalent heterocyclic group having three or more substituents. Since the external quantum efficiency of the light-emitting element is more excellent, the fused ring compound preferably has at least one selected from the group consisting of an aryl group having three or more substituents and a monovalent heterocyclic group having three or more substituents, and more preferably has an aryl group having three or more substituents, and these groups may further have substituents. Examples and preferred ranges of the aryl group and monovalent heterocyclic group in the aryl group having three or more substituents and the monovalent heterocyclic group having three or more substituents are the same as the examples and preferred ranges of the aryl group and monovalent heterocyclic group in the substituent that the heterocyclic group (b) may have, respectively. In the aryl group having three or more substituents and the monovalent heterocyclic group having three or more substituents, examples and preferred ranges of the substituents are the same as the examples and preferred ranges of the substituents that the substituents that the heterocyclic group (b) may further have.

[0297] In an aryl group having three or more substituents and a monovalent heterocyclic group having three or more substituents, the number of substituents is usually 3 to 50, and is preferably 3 to 20, more preferably 3 to 15, even more preferably 3 to 10, particularly preferably 3 to 7, especially preferably 3 to 5, and especially preferably 3 or 4, because this results in better external quantum efficiency of the light-emitting device and facilitates synthesis of the fused ring compound.

[0298] When the fused ring compound has at least one selected from the group consisting of an aryl group having three or more substituents and a monovalent heterocyclic group having three or more substituents, the total number of the aryl group having three or more substituents and the monovalent heterocyclic group having three or more substituents contained in the fused ring compound is usually 1 to 50, and is preferably 1 to 20, more preferably 1 to 10, even more preferably 1 to 7, and particularly preferably 1 to 4, because this results in better external quantum efficiency of the light-emitting device and simplifies the synthesis of the fused ring compound.

[0299] When the fused ring compound has at least one selected from the group consisting of an aryl group having three or more substituents and a monovalent heterocyclic group having three or more substituents, the fused ring compound is not particularly limited as long as it has at least one selected from the group consisting of an aryl group having three or more substituents and a monovalent heterocyclic group having three or more substituents. When the fused ring compound has at least one selected from the group consisting of an aryl group having three or more substituents and a monovalent heterocyclic group having three or more substituents, the fused ring compound may have at least one selected from the group consisting of an aryl group having three or more substituents and a monovalent heterocyclic group having three or more substituents, for example, as a substituent that the heterocyclic group (b) may have, or may have as a further substituent that the substituent that the heterocyclic group (b) may have, but preferably as a substituent that the heterocyclic group (b) may have, because the external quantum efficiency of the light-emitting device is more excellent.

[0300] When the fused ring compound has an aryl group having three or more substituents, the aryl group in the substituent that the heterocyclic group (b) may have may be an aryl group having three or more substituents, and in the substituted amino group in the substituent that the heterocyclic group (b) may have, the aryl group in the substituent that the amino group has may be an aryl group having three or more substituents. Furthermore, when the fused ring compound has a monovalent heterocyclic group having three or more substituents, the monovalent heterocyclic group in the substituent that the heterocyclic group (b) may have may be a monovalent heterocyclic group having three or more substituents, and in the substituted amino group in the substituent that the heterocyclic group (b) may have, the monovalent heterocyclic group in the substituent that the amino group has may be a monovalent heterocyclic group having three or more substituents.

[0301] The sp condensed ring compounds have better external quantum efficiency of light-emitting devices. 3Preferably, the total number of carbon atoms is 9 or more, or the fused ring compound has at least one selected from the group consisting of an aryl group having three or more substituents and a monovalent heterocyclic group having three or more substituents. 3 The total number of carbon atoms is more preferably 9 or more, and the sp 3 It is more preferable that the total number of carbon atoms is 9 or more, and the fused ring compound has at least one selected from the group consisting of an aryl group having three or more substituents and a monovalent heterocyclic group having three or more substituents.

[0302] The fused ring compound is preferably a compound having a heterocyclic skeleton represented by formula (b0) (i.e., the heterocyclic skeleton is a heterocyclic skeleton represented by formula (b0)) because the external quantum efficiency of the light-emitting device is superior. Unless otherwise specified, the examples and preferred ranges of the fused ring compound can also be applied as examples and preferred ranges to compounds having a heterocyclic skeleton represented by formula (b0) or the like described below.

[0303] [ka] [In the formula, X b1 and X b2 are each independently an oxygen atom, a sulfur atom, a selenium atom, -N(R xb )-, an alkylene group, or a cycloalkylene group, and these groups may have a substituent. When a plurality of such substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded. R xb 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. When a plurality of such substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded. Arb1 , Ar b2 and Ar b3 each independently represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent. When a plurality of such substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded. X b1 and Ar b1 , X b1 and Ar b2 , X b2 and Ar b1 , X b2 and Ar b3 , and Ar b2 and Ar b3 may each independently bond directly or via a divalent or higher valent group which may have a substituent to form a ring. When a plurality of such substituents are present, they may be the same or different and may bond to each other to form a ring together with the atoms to which they are bonded. However, the formula (b0) satisfies at least one of the requirements (b0-i) and (b0-ii). (b0-i)Ar b1 , Ar b2 and Ar b3 At least one of the groups is a polycyclic aromatic hydrocarbon group or a polycyclic heterocyclic group, and these groups may have a substituent. (b0-ii)X b1 and Ar b1 , X b1 and Ar b2 , X b2 and Ar b1 , X b2 and Ar b3 , and Ar b2 and Ar b3 At least one of the groups is bonded directly or via a divalent or higher valent group which may have a substituent to form a ring. When a plurality of such substituents is 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 they are bonded.]

[0304] When the fused ring compound satisfies the requirement (i), the nitrogen atom, oxygen atom, sulfur atom, selenium atom, and sp atom contained in the ring of the heterocyclic skeleton represented by formula (b0) are 3 The total number of carbon atoms, not including the number of atoms of the substituents, is 4 or more. When the fused ring compound satisfies the requirement (i), the nitrogen atom, oxygen atom, sulfur atom, selenium atom, and sp atom contained in the fused ring of the heterocyclic skeleton represented by formula (b0) are 3 Examples and preferred ranges of the total number of carbon atoms include the nitrogen atom, oxygen atom, sulfur atom, selenium atom, and sp atom contained in the fused ring of the heterocyclic skeleton when the fused ring compound satisfies the requirement (i). 3 The examples and preferred ranges for the total number of carbon atoms are the same as those for the total number of carbon atoms. When a fused ring compound satisfies requirement (ii), the number of nitrogen atoms contained in the ring of the heterocyclic skeleton represented by formula (b0), not including the number of nitrogen atoms of substituents, is 2 or more. When a fused ring compound satisfies requirement (ii), examples and preferred ranges of the number of nitrogen atoms contained in the fused ring of the heterocyclic skeleton represented by formula (b0) are the same as the examples and preferred ranges of the number of nitrogen atoms contained in the ring of the heterocyclic skeleton when the fused ring compound satisfies requirement (ii).

[0305] X b1 and X b2 is preferably an oxygen atom, a sulfur atom, a selenium atom, or —N(R xb )- or an alkylene group, and more preferably an oxygen atom, a sulfur atom, a selenium atom, or an —N(R xb )-, and more preferably an oxygen atom, a sulfur atom, or a group represented by —N(R xb )-, and particularly preferably an oxygen atom or -N(R xb )-, and these groups may have a substituent. When a plurality of such substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded.

[0306] X b1 and X b2The alkylene group in is preferably a methylene group, ethylene group, propylene group, butylene group, pentylene group, or hexylene group, more preferably a methylene group, ethylene group, or propylene group, and even more preferably a methylene group, and these groups may have a substituent. X b1 and X b2 The cycloalkylene group in the formula (I) is preferably a cyclopropylene group, a cyclobutylene group, a cyclopentylene group or a cyclohexylene group, more preferably a cyclohexylene group, and these groups may have a substituent. X b1 and X b2 The examples and preferred range of the substituents which may be possessed by the heterocyclic group (b) are the same as the examples and preferred range of the substituents which may be possessed by the heterocyclic group (b).

[0307] R xb 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, since the external quantum efficiency of the light-emitting element is more excellent. These groups may have a substituent. R xb The examples and preferred ranges of the aryl group and monovalent heterocyclic group in are the same as the examples and preferred ranges of the aryl group and monovalent heterocyclic group in the substituent that the heterocyclic group (b) may have, respectively. R xb The examples and preferred range of the substituents which may be possessed by the heterocyclic group (b) are the same as the examples and preferred range of the substituents which may be possessed by the heterocyclic group (b).

[0308] Ar b1 , Ar b2 and Ar b3 The aromatic hydrocarbon group in the formula (I) is a monocyclic aromatic hydrocarbon group or a polycyclic aromatic hydrocarbon group, and these groups may have a substituent. Ar b1 , Ar b2 and Ar b3In the above formula, the monocyclic aromatic hydrocarbon group is a group in which one or more hydrogen atoms directly bonded to atoms constituting the ring have been removed from a monocyclic aromatic hydrocarbon ring, and the group may have a substituent.

[0309] Ar b1 , Ar b2 and Ar b3 In the above formula, the number of carbon atoms in the monocyclic aromatic hydrocarbon group, not including the number of carbon atoms in the substituent, is preferably 6 to 20, more preferably 6 to 10, and even more preferably 6. The monocyclic aromatic hydrocarbon ring in the monocyclic aromatic hydrocarbon group is preferably benzene, as this provides a light-emitting device with better external quantum efficiency.

[0310] Ar b1 , Ar b2 and Ar b3 In the formula (I), the polycyclic aromatic hydrocarbon group is a group in which one or more hydrogen atoms directly bonded to atoms constituting the ring have been removed from a polycyclic aromatic hydrocarbon ring, and the group may have a substituent.

[0311] Ar b1 , Ar b2 and Ar b3 In the formula, the number of carbon atoms of the polycyclic aromatic hydrocarbon group is usually 7 to 60, preferably 8 to 60, more preferably 9 to 40, and even more preferably 10 to 20, not including the number of carbon atoms of the substituent. Ar b1 , Ar b2 and Ar b3 In the above, the polycyclic aromatic hydrocarbon ring in the polycyclic aromatic hydrocarbon group is preferably a bicyclic to heptacyclic aromatic hydrocarbon ring, more preferably a bicyclic to pentacyclic aromatic hydrocarbon ring, still more preferably a bicyclic or tricyclic aromatic hydrocarbon ring, particularly preferably naphthalene, indene, anthracene, phenanthrene, dihydrophenanthrene or fluorene, and particularly preferably naphthalene, anthracene, phenanthrene or fluorene, because this provides a light-emitting device with better external quantum efficiency.

[0312] Arb1 , Ar b2 and Ar b3 The aromatic hydrocarbon group in the formula (I) is preferably a monocyclic aromatic hydrocarbon group, and more preferably a group in which one or more hydrogen atoms directly bonded to atoms constituting the ring have been removed from benzene, since this provides a light-emitting device with better external quantum efficiency, and these groups may have a substituent.

[0313] Ar b1 , Ar b2 and Ar b3 The heterocyclic group in the formula (I) is a monocyclic heterocyclic group or a polycyclic heterocyclic group, and these groups may have a substituent. Ar b1 , Ar b2 and Ar b3 In the above formula, the monocyclic heterocyclic group is a group in which one or more hydrogen atoms directly bonded to atoms constituting the ring have been removed from a monocyclic heterocycle, and the group may have a substituent.

[0314] Ar b1 , Ar b2 and Ar b3 In the above formula, the number of carbon atoms in the monocyclic heterocyclic group, not including the number of carbon atoms in the substituents, is preferably 1 to 20, more preferably 1 to 10, even more preferably 2 to 6, and particularly preferably 3 to 5. The number of heteroatoms in the monocyclic heterocyclic group, not including the number of heteroatoms in the substituents, is preferably 1 to 10, more preferably 1 to 5, even more preferably 1 to 3, and particularly preferably 1 or 2. Ar b1 , Ar b2 and Ar b3 In the above, the monocyclic heterocycle in the monocyclic heterocyclic group is preferably furan, thiophene, pyrrole, triazole, pyridine, diazabenzene, or triazine, because the external quantum efficiency of the light-emitting device is more excellent, more preferably furan, thiophene, pyrrole, triazole, pyridine, or diazabenzene, and even more preferably pyridine or diazabenzene.

[0315] Ar b1, Ar b2 and Ar b3 In the above formula, the polycyclic heterocyclic group is a group in which one or more hydrogen atoms directly bonded to atoms constituting the ring have been removed from a polycyclic heterocycle, and the group may have a substituent. Ar b1 , Ar b2 and Ar b3 In the above, the polycyclic heterocyclic ring in the polycyclic heterocyclic group may be a heterocyclic ring having a polycyclic heterocyclic skeleton (b') described later, or may be a heterocyclic ring not having a polycyclic heterocyclic skeleton (b') described later. b1 , Ar b2 and Ar b3 In the formula (I), the polycyclic heterocyclic group may be the heterocyclic group (b') described below, or may be a heterocyclic group (Nb') in which one or more hydrogen atoms directly bonded to atoms constituting the ring have been removed from a heterocycle not having a polycyclic heterocyclic skeleton (b').

[0316] The number of carbon atoms contained in the ring of the heterocyclic group (Nb'), not including the number of carbon atoms of the substituent, is usually 1 to 60, preferably 5 to 40, and more preferably 8 to 20. The number of heteroatoms contained in the ring of the heterocyclic group, not including the number of heteroatoms of the substituent, is usually 1 to 30, preferably 1 to 10, more preferably 1 to 5, even more preferably 1 to 3, and particularly preferably 1 or 2.

[0317] In the heterocyclic group (Nb'), the heterocycle not having a heterocyclic skeleton (b') is not particularly limited as long as it is a heterocycle not having a heterocyclic skeleton (b') as described below. A polycyclic heterocycle not having a heterocyclic skeleton (b') provides a light-emitting device with better external quantum efficiency, and is therefore preferably a bicyclic to heptacyclic heterocycle not having a heterocyclic skeleton (b'), more preferably a bicyclic to pentacyclic heterocycle not having a heterocyclic skeleton (b'), still more preferably a bicyclic or tricyclic heterocycle not having a heterocyclic skeleton (b'), and particularly preferably a tricyclic heterocycle not having a heterocyclic skeleton (b'). A heterocycle not having a polycyclic heterocyclic skeleton (b') has better external quantum efficiency of a light-emitting device, and therefore is preferably azanaphthalene, diazanaphthalene, benzofuran, benzothiophene, indole, azaindole, diazaindole, dibenzofuran, dibenzothiophene, dibenzoselenophene, carbazole, azacarbazole, diazacarbazole, phenoxazine, phenothiazine, 9,10-dihydroacridine, 5,10-dihydrophenazine, acridone, azaanthracene, diazaanthracene, azaphenone, 9,10-dihydroacridine, 5,10-dihydrophenazine, acridone, azaanthracene, diazaanthracene, azaphenone, 9,10-dihydroacridine, 5,10-dihydrophenazine, acridone, azaanthracene, diazaanthracene, azaphenone, 9,10-dihydroacridine, 5,10-dihydrophenazine, azaphenone, 9,10-dihydroacridine, 5,10-dihydrophenazine, azaphenone, 9,10-dihydroacridine, diazaphenone ... and azanaphthalene, diazanaphthalene, dibenzofuran, dibenzothiophene, carbazole, azacarbazole, diazacarbazole, azaanthracene, diazaanthracene, azaphenanthrene, or diazaphenanthrene, and further preferably azanaphthalene, diazanaphthalene, azaanthracene, diazaanthracene, azaphenanthrene, or diazaphenanthrene, and particularly preferably azaphenanthrene or diazaphenanthrene.

[0318] The heterocyclic skeleton (b') is composed of a boron atom, a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, and sp 3 and at least one selected from the group consisting of carbon atoms in a fused ring.

[0319] The number of carbon atoms contained in the fused ring of the heterocyclic skeleton (b') is usually 1 to 60, preferably 5 to 50, more preferably 10 to 40, and even more preferably 15 to 30, not including the number of carbon atoms of the substituent. The number of heteroatoms contained in the fused ring of the heterocyclic skeleton (b') is usually 2 to 30, preferably 2 to 15, more preferably 2 to 10, even more preferably 2 to 5, and particularly preferably 2 or 3, not including the number of heteroatoms of the substituents. The number of boron atoms contained in the fused ring of the heterocyclic skeleton (b') is usually 1 to 10, preferably 1 to 5, more preferably 1 to 3, and even more preferably 1, not including the number of boron atoms in the substituents. The nitrogen atom, oxygen atom, sulfur atom, selenium atom and sp atom contained in the fused ring of the heterocyclic skeleton (b') 3 The total number of carbon atoms, not including the number of atoms of substituents, is usually 1 to 20, preferably 1 to 10, more preferably 1 to 5, still more preferably 1 to 3, and particularly preferably 2.

[0320] The heterocyclic skeleton (b') preferably contains a boron atom and at least one atom selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, and a selenium atom in the fused ring, because this provides a light-emitting device with better external quantum efficiency; it is more preferable that the heterocyclic skeleton (b') contains a boron atom and at least one atom selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom in the fused ring; it is even more preferable that the heterocyclic skeleton (b') contains a boron atom and at least one atom selected from the group consisting of a nitrogen atom and an oxygen atom in the fused ring; it is particularly preferable that the heterocyclic skeleton (b') contains a boron atom and a nitrogen atom in the fused ring; and it is especially preferable that the heterocyclic skeleton (b') contains a nitrogen atom that does not form a double bond with the boron atom in the fused ring.

[0321] The heterocyclic skeleton (b') is preferably a heterocyclic skeleton having two or more rings, more preferably a heterocyclic skeleton having three or more rings, even more preferably a heterocyclic skeleton having four or more rings, and particularly preferably a heterocyclic skeleton having five or more rings, because the external quantum efficiency of the light-emitting device is superior. The heterocyclic skeleton (b) may be, for example, a heterocyclic skeleton having 40 or less rings, or a heterocyclic skeleton having 30 or less rings, but is preferably a heterocyclic skeleton having 20 or less rings, more preferably a heterocyclic skeleton having 15 or less rings, even more preferably a heterocyclic skeleton having 10 or less rings, and particularly preferably a heterocyclic skeleton having 7 or less rings, because the external quantum efficiency of the light-emitting device is superior.

[0322] The heterocyclic skeleton (b') can also be referred to as a heterocyclic group (b') containing the heterocyclic skeleton (b'). Examples and preferred ranges of the substituents which the heterocyclic group (b') may have are the same as the examples and preferred ranges of the substituents which the heterocyclic group (b) may have.

[0323] Ar b1, Ar b2 and Ar b3 The heterocyclic group in the formula (I) is preferably a heterocyclic group (Nb') or a heterocyclic group (b'), and more preferably a heterocyclic group (b'), because the external quantum efficiency of the light-emitting device is better. These groups may have a substituent.

[0324] Ar b1 , Ar b2 and Ar b3 is a monocyclic aromatic hydrocarbon group, a polycyclic aromatic hydrocarbon group, a monocyclic heterocyclic group, a heterocyclic group (Nb') or a heterocyclic group (b'), and is preferably a monocyclic aromatic hydrocarbon group, a group in which one or more hydrogen atoms directly bonded to atoms constituting the ring have been removed from a bicyclic to pentacyclic aromatic hydrocarbon ring, a monocyclic heterocyclic group, a group in which one or more hydrogen atoms directly bonded to atoms constituting the ring have been removed from a bicyclic to pentacyclic heterocycle not having a heterocyclic skeleton (b'), or a heterocyclic group (b'), since this results in a more excellent external quantum efficiency of the light-emitting element. The heterocyclic group (b') is preferably a monocyclic aromatic hydrocarbon group, a monocyclic heterocyclic group, a bicyclic or tricyclic heterocyclic ring not having a heterocyclic skeleton (b') from which one or more hydrogen atoms directly bonded to an atom constituting the ring have been removed, or a heterocyclic group (b'), more preferably a monocyclic aromatic hydrocarbon group, a monocyclic heterocyclic group, a bicyclic or tricyclic heterocyclic ring not having a heterocyclic skeleton (b') from which one or more hydrogen atoms directly bonded to an atom constituting the ring have been removed, or a heterocyclic group (b'), particularly preferably a monocyclic aromatic hydrocarbon group, a bicyclic or tricyclic heterocyclic ring not having a heterocyclic skeleton (b') from which one or more hydrogen atoms directly bonded to an atom constituting the ring have been removed, or a heterocyclic group (b'), and particularly preferably a monocyclic aromatic hydrocarbon group or a heterocyclic group (b'), and these groups may have a substituent. Ar b1 , Ar b2 and Ar b3 The examples and preferred range of the substituents which may be possessed by the heterocyclic group (b) are the same as the examples and preferred range of the substituents which may be possessed by the heterocyclic group (b).

[0325] The fused ring compound having a heterocyclic skeleton (b) with 6 or more rings provides a light-emitting device with better external quantum efficiency. Therefore, when formula (b0) satisfies at least one of requirements (b0-i) and (b0-ii), the compound having a heterocyclic skeleton represented by formula (b0) has a heterocyclic skeleton with 6 or more rings, and the light-emitting device with better external quantum efficiency.

[0326] If formula (b0) satisfies requirement (b0-i), then Ar b1 , Ar b2 and Ar b3 At least one of the groups is a polycyclic aromatic hydrocarbon group or a polycyclic heterocyclic group, and since the external quantum efficiency of the light-emitting device is more excellent, it is preferably a polycyclic heterocyclic group, more preferably a group in which one or more hydrogen atoms directly bonded to atoms constituting the ring have been removed from a bicyclic to pentacyclic heterocycle not having a heterocyclic skeleton (b'), or a heterocyclic group (b'), even more preferably a group in which one or more hydrogen atoms directly bonded to atoms constituting the ring have been removed from a bicyclic or tricyclic heterocycle not having a heterocyclic skeleton (b'), or a heterocyclic group (b'), and particularly preferably a heterocyclic group (b'), and these groups may have a substituent.

[0327] When formula (b0) satisfies requirement (b0-i), the external quantum efficiency of the light-emitting device is better, so Ar b1 , Ar b2 and Ar b3 At least one of the groups (a) and (b) is preferably a polycyclic heterocyclic group, more preferably a heterocyclic group (b'), and these groups may have a substituent.

[0328] When formula (b0) satisfies the requirement (b0-i), the external quantum efficiency of the light-emitting device is better, so preferably, Ar b1 and Ar b2 At least one of Ar is a polycyclic aromatic hydrocarbon group or a polycyclic heterocyclic group (preferably a polycyclic heterocyclic group), b2is more preferably a polycyclic aromatic hydrocarbon group or a polycyclic heterocyclic group (preferably a polycyclic heterocyclic group), and Ar b2 is more preferably a heterocyclic group (b'), and these groups may have a substituent.

[0329] Formula (b0) satisfies requirement (b0-i) and Ar b1 , Ar b2 and Ar b3 is other than the heterocyclic group (b'), Ar b1 , Ar b2 and Ar b3 Examples and preferred ranges of Ar are described later. b , Ar b4 and Ar b5 The examples and preferred ranges are the same as those of the above.

[0330] When formula (b0) satisfies requirement (b0-i), the heterocyclic group (b') is preferably a group represented by formula (b1'-1) to formula (b1'-4), more preferably a group represented by formula (b1'-2) or formula (b1'-3), and even more preferably a group represented by formula (b1'-2), since the external quantum efficiency of the light-emitting device is more excellent.

[0331] [ka] [In the formula, R xb represents the same meaning as above. Ar b , Ar b4 and Ar b5 each independently represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent. When a plurality of such substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded. X b3 , X b4 and X b5 are each independently an oxygen atom, a sulfur atom, a selenium atom, -N(R xb)-, an alkylene group, or a cycloalkylene group, and these groups may have a substituent. When a plurality of such substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded. n b1’ represents 2 or 3. However, Ar b1 When is a group represented by formula (b1'-1) to formula (b1'-4), n b1’ represents 3. Ar b2 or Ar b3 When is a group represented by formula (b1'-1) to formula (b1'-4), n b1’ represents 2. * b1’ represents the bond position. b1 When the group is represented by formula (b1'-1) to formula (b1'-4), three * b1’ are, respectively, X b1 , X b2 and a bond with a boron atom. b2 When is a group represented by formula (b1'-1) to formula (b1'-4), two * b1’ are, respectively, X b1 and a bond with a boron atom. b3 When is a group represented by formula (b1'-1) to formula (b1'-4), two * b1’ are, respectively, X b2 and a bond with a boron atom. X b3 and Ar b , X b3 and Ar b4 , X b4 and Ar b4 , X b4 and Ar b5 , X b5 and Ar b5 , and X b5 and Ar b may each independently bond directly or via a divalent or higher valent group which may have a substituent to form a ring, and in formula (b1'-1) and formula (b1'-3), Ar b4 and Ar b5may be bonded directly or via a divalent or higher valent group which may have a substituent to form a ring, and in formula (b1'-1) and formula (b1'-2), Ar b and Ar b5 may be bonded directly or via a divalent or higher group which may have a substituent to form a ring. When there are multiple substituents in the divalent or higher group, they may be the same or different and may be bonded to each other to form a ring together with the atom to which they are bonded.

[0332] Ar b , Ar b4 and Ar b5 Examples of the aromatic hydrocarbon group and preferred ranges thereof are Ar b1 , Ar b2 and Ar b3 The examples and preferred ranges of the aromatic hydrocarbon group are the same as those in the above. Ar b , Ar b4 and Ar b5 Examples and preferred ranges of the heterocyclic group in b1 , Ar b2 and Ar b3 The examples and preferred ranges of the heterocyclic group are the same as those in Ar b , Ar b4 and Ar b5 The heterocyclic group in formula (b0) is preferably a monocyclic heterocyclic group or a heterocyclic group (Nb'), more preferably a monocyclic heterocyclic group, and these groups may have a substituent, because the external quantum efficiency of the light-emitting device is better and the compound having the heterocyclic skeleton represented by formula (b0) can be easily synthesized.

[0333] Ar b , Ar b4 and Ar b5 is preferably an aromatic hydrocarbon group which may have a substituent, since the external quantum efficiency of the light-emitting element is superior and the compound having a heterocyclic skeleton represented by formula (b0) is easily synthesized.

[0334] Ar b , Ar b4 and Arb5 is preferably a monocyclic aromatic hydrocarbon group, a polycyclic monocyclic heterocyclic group, a monocyclic heterocyclic group, or a heterocyclic group (Nb'), since this leads to a more excellent external quantum efficiency of the light-emitting device and allows for easy synthesis of a compound having a heterocyclic skeleton represented by formula (b0), and more preferably a monocyclic aromatic hydrocarbon group, a group in which one or more hydrogen atoms directly bonded to atoms constituting the ring have been removed from a bicyclic to pentacyclic aromatic hydrocarbon ring, a monocyclic heterocyclic group, or a group in which one or more hydrogen atoms directly bonded to atoms constituting the ring have been removed from a bicyclic to pentacyclic heterocycle not having a heterocyclic skeleton (b'), and even more preferably , a monocyclic aromatic hydrocarbon group, a group in which one or more hydrogen atoms directly bonded to an atom constituting the ring have been removed from a bicyclic or tricyclic aromatic hydrocarbon ring, a monocyclic heterocyclic group, or a group in which one or more hydrogen atoms directly bonded to an atom constituting the ring have been removed from a bicyclic or tricyclic heterocyclic ring that does not have a heterocyclic skeleton (b'), and particularly preferred are monocyclic aromatic hydrocarbon groups, or groups in which one or more hydrogen atoms directly bonded to an atom constituting the ring have been removed from a bicyclic or tricyclic aromatic hydrocarbon ring, and even more preferred are monocyclic aromatic hydrocarbon groups, and these groups may have a substituent. Ar b , Ar b4 and Ar b5 Examples of the substituents that may be possessed by Ar and the preferred range thereof are as follows: b1 , Ar b2 and Ar b3 The examples and preferred ranges of the substituents that may be possessed by the group are the same as those of the substituents that may be possessed by the group.

[0335] X b3 , X b4 and X b5 Examples and preferred ranges of X b1 and X b2 The examples and preferred ranges are the same as those of the above. Examples and preferred ranges of the divalent or more groups which may have a substituent in formulas (b1'-1) to (b1'-4) are the same as the examples and preferred ranges of the divalent or more groups which may have a substituent described later in the section regarding the case where formula (b0) satisfies requirement (b0-ii).

[0336] When formula (b0) satisfies requirement (b0-i), a compound having a heterocyclic skeleton represented by formula (b0) has better external quantum efficiency of a light-emitting element, and is therefore preferably a compound having a heterocyclic skeleton represented by formulas (b0-1-1) to (b0-1-3) (i.e., the heterocyclic skeleton represented by formula (b0) is the heterocyclic skeleton represented by formulas (b0-1-1) to (b0-1-3)), and more preferably a compound having a heterocyclic skeleton represented by formula (b0-1-1) (i.e., the heterocyclic skeleton represented by formula (b0) is the heterocyclic skeleton represented by formula (b0-1-1)).

[0337] [ka] [In the formula, Ar b , Ar b1 , Ar b2 , Ar b3 , Ar b4 , Ar b5 , X b1 , X b2 , X b3 , X b4 and X b5 has the same meaning as above.]

[0338] In formulas (b0-1-1) to (b0-1-3), Ar b1 , Ar b2 and Ar b3 is other than the heterocyclic group (b'), Ar b1 , Ar b2 and Ar b3 Examples and preferred ranges of Ar b , Ar b4 and Ar b5 The examples and preferred ranges are the same as those of the above.

[0339] Formula (b0) satisfies requirement (b0-ii) and Ar b1 , Ar b2 and Ar b3 is other than the heterocyclic group (b'), Ar b1 , Ar b2 and Ar b3 Examples and preferred ranges of Ar b , Arb4 and Ar b5 The examples and preferred ranges are the same as those of the above.

[0340] When formula (b0) satisfies requirement (b0-ii), the external quantum efficiency of the light-emitting device is superior, so that X b1 and Ar b1 , X b1 and Ar b2 , X b2 and Ar b1 , and X b2 and Ar b3 Preferably, at least one of the following is bonded directly or via a divalent or higher valent group which may have a substituent to form a ring; and X b1 and Ar b2 , and X b2 and Ar b3 It is more preferable that at least one of the following is bonded directly or via a divalent or higher valent group which may have a substituent to form a ring; and X b2 and Ar b3 However, it is more preferable that they are bonded directly or via a divalent or higher valent group which may have a substituent to form a ring.

[0341] When formula (b0) satisfies requirement (b0-ii), the divalent or higher valent group is preferably a divalent to tetravalent group, more preferably a divalent or trivalent group, since the external quantum efficiency of the light-emitting device is superior and the compound represented by formula (b0) can be easily synthesized, and these groups may have a substituent.

[0342] When formula (b0) satisfies requirement (b0-ii), the divalent group is preferably an alkylene group, a cycloalkylene group, or a -N(R 0 )-, -B(R 0 )-, a group represented by -O-, a group represented by -S-, or a group represented by -Se-, and more preferably an alkylene group, -N(R 0 )-, -B(R 0)-, -O-, -S- or -Se-, and more preferably -N(R 0 )-, -B(R 0 )-, -O-, -S- or -Se-, and particularly preferably -N(R 0 )-, -B(R 0 )-, -O-, or -S-, and particularly preferably -N(R 0 )-, -B(R 0 )- or -O-, and these groups may have a substituent.

[0343] When formula (b0) satisfies requirement (b0-ii), the trivalent group is preferably a group in which one hydrogen atom has been removed from an alkylene group, a group in which one hydrogen atom has been removed from a cycloalkylene group, or a group represented by formula (Xb0-1), because this provides a light-emitting device with better external quantum efficiency and facilitates the synthesis of a compound having a heterocyclic skeleton represented by formula (b0), more preferably a group in which one hydrogen atom has been removed from an alkylene group or a group represented by formula (Xb0-1), and even more preferably a group represented by formula (Xb0-1), and these groups may have a substituent.

[0344] [ka] [where, X b0-1 is a boron atom, a nitrogen atom, a phosphorus atom, P(=O), Si(R 0 ) or Ge(R 0 ) represents.

[0345] X b0-1 is preferably a boron atom, a nitrogen atom, a phosphorus atom or P(═O), more preferably a boron atom or a nitrogen atom, and even more preferably a boron atom, since this provides a light-emitting device with better external quantum efficiency.

[0346] When formula (b0) satisfies requirement (b0-ii), the tetravalent group is preferably a group in which two hydrogen atoms have been removed from an alkylene group, a group in which two hydrogen atoms have been removed from a cycloalkylene group, or a group represented by formula (Xb0-2), because this provides a light-emitting device with better external quantum efficiency and facilitates the synthesis of a low-molecular-weight compound having a heterocyclic skeleton represented by formula (b0), and more preferably a group in which two hydrogen atoms have been removed from an alkylene group or a group represented by formula (Xb0-2), and these groups may have a substituent.

[0347] [ka] [In the formula, X b0-2 represents a silicon atom or a germanium atom.

[0348] R in a divalent or higher group when formula (b0) satisfies requirement (b0-ii) 0 Examples and preferred ranges of R xb In the divalent or higher valent group in the case where formula (b0) satisfies requirement (b0-ii), examples and preferred ranges of the alkylene group and cycloalkylene group are the same as those of X b1 and X b2 When formula (b0) satisfies requirement (b0-ii), examples and preferred ranges of the substituents that the divalent or higher group may have are the same as the examples and preferred ranges of the substituents that the heterocyclic group (b) may have.

[0349] When formula (b0) satisfies requirement (b0-ii), a compound having a heterocyclic skeleton represented by formula (b0) has better external quantum efficiency of a light-emitting element, and is therefore preferably a compound having a heterocyclic skeleton represented by formulas (b0-2-1) to (b0-2-4) (i.e., the heterocyclic skeleton represented by formula (b0) is the heterocyclic skeleton represented by formulas (b0-2-1) to (b0-2-4)), more preferably a compound having a heterocyclic skeleton represented by formula (b0-2-1) or formula (b0-2-3) (i.e., the heterocyclic skeleton represented by formula (b0) is the heterocyclic skeleton represented by formula (b0-2-1) or formula (b0-2-3)), and even more preferably a compound having a heterocyclic skeleton represented by formula (b0-2-1) (i.e., the heterocyclic skeleton represented by formula (b0) is the heterocyclic skeleton represented by formula (b0-2-1)).

[0350] [ka] [In the formula, Ar b1 , Ar b2 , Ar b3 and X b2 represents the same meaning as above. Ar xb1 and Ar xb2 each independently represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent. When a plurality of such substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded. X xb1 , X xb2 and X xb3 are each independently a direct bond, an oxygen atom, a sulfur atom, a selenium atom, or -N(R xb )-, -B(R xb )-, an alkylene group, or a cycloalkylene group, and these groups may have a substituent. When a plurality of such substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded. R xb represents the same meaning as above. X xb1and Ar xb1 , X xb1 and Ar b2 , X xb2 and Ar xb1 , X xb2 and Ar b1 , X xb3 and Ar xb2 , and X xb3 and Ar b3 may each independently bond directly or via a divalent or higher valent group which may have a substituent to form a ring, and in formula (b0-2-1) and formula (b0-2-3), Ar b1 and Ar xb1 may be bonded directly or via a divalent or higher valent group which may have a substituent to form a ring, and in formula (b0-2-2) and formula (b0-2-4), Ar b2 and Ar xb1 may be bonded directly or via a divalent or higher valent group which may have a substituent to form a ring, and in formula (b0-2-3) and formula (b0-2-4), Ar b1 and Ar xb2 may be bonded directly or via a divalent or higher group which may have a substituent to form a ring. When there are multiple substituents in the divalent or higher group, they may be the same or different and may be bonded to each other to form a ring together with the atom to which they are bonded.

[0351] Ar xb1 and Ar xb2 Examples and preferred ranges of Ar b , Ar b4 and Ar b5 The examples and preferred ranges are the same as those of the above.

[0352] In formulas (b0-1-1) to (b0-1-3), Ar b1 , Ar b2 and Ar b3 is other than the heterocyclic group (b'), Ar b1 , Ar b2 and Ar b3 Examples and preferred ranges of Ar b , Ar b4 and Arb5 The examples and preferred ranges are the same as those of the above.

[0353] X xb1 , X xb2 and X xb3 is preferably a direct bond, an oxygen atom, a sulfur atom, a selenium atom, or —N(R xb )- or -B(R xb )-, and more preferably a direct bond, an oxygen atom, a sulfur atom, or —N(R xb )- or -B(R xb )-, and more preferably a direct bond, an oxygen atom, or —N(R xb )- or -B(R xb )-, and particularly preferably, -N(R xb )- or -B(R xb )-, and particularly preferably -B(R xb )-, and these groups may have a substituent. X xb1 , X xb2 and X xb3 Examples of the substituents that may be possessed by X and the preferred range thereof are as follows: b1 and X b2 The examples and preferred ranges of the substituents that may be possessed by the group are the same as those of the substituents that may be possessed by the group.

[0354] Examples and preferred ranges of the divalent or higher valent groups which may have a substituent in formulas (b0-2-1) to (b0-2-4) are the same as the examples and preferred ranges of the divalent or higher valent groups which may have a substituent described in the section when formula (b0) satisfies requirement (b0-ii).

[0355] Since the fused ring compound has better external quantum efficiency of the light-emitting element, it is preferably a compound having a heterocyclic skeleton represented by formula (b0-1-1) to formula (b0-1-3) or formula (b0-2-1) to formula (b0-2-4), more preferably a compound having a heterocyclic skeleton represented by formula (b0-1-1), formula (b0-1-2), formula (b0-2-1) or formula (b0-2-3), even more preferably a compound having a heterocyclic skeleton represented by formula (b0-1-1), formula (b0-2-1) or formula (b0-2-3), and particularly preferably a compound having a heterocyclic skeleton represented by formula (b0-1-1).

[0356] The compound having a heterocyclic skeleton represented by formula (b0) has a better external quantum efficiency of the light-emitting device, and therefore preferably satisfies at least one of requirement (i) and requirement (ii), and more preferably satisfies both requirement (i) and requirement (ii).

[0357] When a fused ring compound satisfies requirement (i), the external quantum efficiency of the light-emitting device is superior. Therefore, the fused ring compound is preferably a compound having a heterocyclic skeleton represented by formula (b0-1-1) to formula (b0-1-3), formula (b0-2-3) or formula (b0-2-4), more preferably a compound having a heterocyclic skeleton represented by formula (b0-1-1) to formula (b0-1-3), even more preferably a compound having a heterocyclic skeleton represented by formula (b0-1-1) or formula (b0-1-2), and particularly preferably a compound having a heterocyclic skeleton represented by formula (b0-1-1).

[0358] When the fused ring compound satisfies the requirement (ii), the external quantum efficiency of the light-emitting device is superior, and therefore, in formula (b0-1-1) and formula (b0-1-2), X b1 , X b2 , X b3 and X b4 At least two of the following are -N(R xb When the fused ring compound satisfies the requirement (ii), X in formula (b0-1-3) is preferably a group represented by the formula (b0-1-4). b1 , X b2 , X b3 and X b5At least two of the following are -N(R xb When the fused ring compound satisfies the requirement (ii), X in formula (b0-2-1) is preferably a group represented by the formula (b0-2-2). xb1 and X b2 At least one of -N(R xb When the fused ring compound satisfies the requirement (ii), X in formula (b0-2-2) is preferably a group represented by the formula (b0-2-3). xb2 and X b2 At least one of -N(R xb )- is preferably a group represented by the formula:

[0359] When the fused ring compound satisfies the requirements (i) and (ii), the external quantum efficiency of the light-emitting device is superior. Therefore, the fused ring compound is preferably a compound having a heterocyclic skeleton represented by formula (b0-1-1) or formula (b0-1-2), and in formula (b0-1-1) and formula (b0-1-2), X b1 , X b2 , X b3 and X b4 At least two of the following are -N(R xb It is preferable that the compound is a low molecular weight compound having a heterocyclic skeleton represented by formula (b0-1-1), and in formula (b0-1-1), X b1 , X b2 , X b3 and X b4 At least two of the following are -N(R xb )- is more preferable.

[0360] A compound having a heterocyclic skeleton represented by formula (b0-1-1), wherein X b1 , X b2 , X b3 and X b4 At least two of the following are -N(R xb The compound having the group represented by formula (b0-1-1′) may be, for example, a compound having a heterocyclic skeleton represented by formula (b0-1-1′).

[0361] [ka] [In the formula, Ar b , Ar b1 , Ar b3 , Ar xb1 , Ar b4 , Ar b5 , X b2 , X b4 and X b0-1 represents the same meaning as above. Ar xb3 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent. When a plurality of such substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded. Ar b1 and Ar xb1 , Ar xb1 and Ar xb3 , and Ar xb3 and Ar b4 may each independently bond directly or via a divalent or higher group which may have a substituent to form a ring. When there are multiple substituents in the divalent or higher group, they may be the same or different and may bond to each other to form a ring together with the atom to which they are bonded.

[0362] Ar xb3 Examples and preferred ranges of Ar xb1 and Ar xb2 The examples and preferred ranges are the same as those of the above.

[0363] Examples and preferred ranges of the divalent or higher group which may have a substituent in formula (b0-1-1') are the same as the examples and preferred ranges of the divalent or higher group which may have a substituent described in the section when formula (b0) satisfies requirement (b0-ii).

[0364] (Fused ring compound represented by formula (BM-1)) As described above, the fused ring compound preferably satisfies requirement (i) and is more preferably a compound having a heterocyclic skeleton represented by formula (b0-1-1). However, since the external quantum efficiency of the light-emitting device is further improved, the fused ring compound is even more preferably a compound represented by formula (BM-1).

[0365] [ka] [In formula (BM-1), Ring R b1 , ring R b2 , ring R b3 , ring R b4 and ring R b5 each independently represents an aromatic hydrocarbon ring or a heterocyclic ring, and these rings may have a substituent. When a plurality of such substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded. X b1 , X b2 , X b3 and X b4 are each independently an oxygen atom, a sulfur atom, a selenium atom, -N(R xb )-, an alkylene group, or a cycloalkylene group, and these groups may have a substituent. When a plurality of such substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded. Ring R b1 , ring R b2 , ring R b3 , ring R b4 , ring R b5 , X b1 , X b2 , X b3 and X b4 At least one of them has a polymerizable group. R xbrepresents 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 such substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded. X b1 and ring R b1 , X b1 and ring R b2 , X b2 and ring R b1 , X b2 and ring R b3 , X b3 and ring R b2 , X b3 and ring R b4 , X b4 and ring R b4 , X b4 and ring R b5 , ring R b2 and ring R b3 , ring R b2 and ring R b5 , and ring R b3 and ring R b5 may each independently bond directly or via a divalent or higher valent group which may have a substituent to form a ring. When a plurality of such substituents are present, they may be the same or different and may bond to each other to form a ring together with the atom to which they are bonded.

[0366] As described above, it is preferable that the fused ring compound further satisfies the requirement (ii), and the external quantum efficiency of the light-emitting device is further improved. b1 , X b2 , X b3 and X b4 At least two of the following are -N(R xb )- is preferably a group represented by the formula:

[0367] Ring R in formula (BM-1) b1 , ring R b2 and ring R b3 Examples and preferred ranges of the aromatic hydrocarbon ring and heterocyclic ring in Ar b1 , Ar b2 and Arb3 The examples and preferred ranges of the aromatic hydrocarbon ring and heterocyclic ring are the same as those explained in the section on aromatic hydrocarbon groups and heterocyclic groups in the above. Ring R in formula (BM-1) b4 and ring R b5 Examples and preferred ranges of the aromatic hydrocarbon ring and heterocyclic ring in Ar b4 and Ar b5 The examples and preferred ranges of the aromatic hydrocarbon ring and heterocyclic ring are the same as those explained in the section on aromatic hydrocarbon groups and heterocyclic groups in the above. Ring R b1 , ring R b2 , ring R b3 , ring R b4 and ring R b5 Examples of the substituents that may be possessed by Ar and the preferred range thereof are as follows: b1 , Ar b2 and Ar b3 The examples and preferred ranges of the substituents that may be possessed by the group are the same as those of the substituents that may be possessed by the group. Ring R b1 , ring R b2 , ring R b3 , ring R b4 and ring R b5 Since has one or more bonds, the ring R b1 , ring R b2 , ring R b3 , ring R b4 and ring R b5 The aromatic hydrocarbon ring and heterocyclic ring in the formula (I) can also be referred to as an aromatic hydrocarbon group and a heterocyclic group, respectively.

[0368] Therefore, the ring R b1 , ring R b2 , ring R b3 , ring R b4 and ring R b5 Examples and preferred ranges of Ar in formula (b0) are b1 , Ar b , Ar b3 , Ar b4 and Ar b5 Similarly, the examples and preferred ranges of X in formula (BM-1) can be applied. b1 , X b2 , X b3 and X b4The examples and preferred ranges of X are described in the section on formula (b0). b1 , X b2 , X b3 and X b4 Similarly, the examples and preferred ranges of the divalent or more groups which may have a substituent in formula (BM-1) are the same as the examples and preferred ranges of the divalent or more groups which may have a substituent described in the section on the case where formula (b0) satisfies requirement (b0-ii).

[0369] Ring R b1 , ring R b2 , ring R b3 , ring R b4 and ring R b5 is preferably an aromatic hydrocarbon ring, more preferably a monocyclic aromatic hydrocarbon ring, and even more preferably a benzene ring, since the external quantum efficiency of the light-emitting element is superior, and these rings may have a substituent.

[0370] As described above, the fused ring compound represented by formula (BM-1) has excellent external quantum efficiency of the light-emitting device, and therefore, the sp 3 The total number of carbon atoms is preferably 9 or more. Furthermore, since the fused ring compound represented by formula (BM-1) provides a light-emitting device with a more excellent external quantum efficiency, it is preferable that the fused ring compound represented by formula (BM-1) has at least one selected from the group consisting of an aryl group having three or more substituents and a monovalent heterocyclic group having three or more substituents. Since the fused ring compound represented by formula (BM-1) provides a light-emitting device with a more excellent external quantum efficiency, it is preferable that the sp 3 It is preferable that the total number of carbon atoms is 9 or more, and the fused ring compound represented by formula (BM-1) has at least one selected from the group consisting of an aryl group having three or more substituents and a monovalent heterocyclic group having three or more substituents.

[0371] The fused ring compound represented by formula (BM-1) may be, for example, a fused ring compound represented by formula (b1-2-0).

[0372] [ka] [In the formula, Ring R b1 , ring R b2 , ring R b3 , ring R b4 , ring R b5 , X b2 , X b4 and X b0-1 represents the same meaning as above. Ring R Xb1 and ring R Xb2 each independently represents an aromatic hydrocarbon ring or a heterocyclic ring, and these rings may have a substituent. When a plurality of such substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded. Ring R Xb1 and ring R b1 , ring R Xb1 and ring R Xb2 , and ring R Xb2 and ring R b4 may each independently bond directly or via a divalent or higher group which may have a substituent to form a ring. When there are multiple substituents in the divalent or higher group, they may be the same or different and may bond to each other to form a ring together with the atom to which they are bonded.

[0373] Ring R Xb1 and ring R Xb2 Examples and preferred ranges of the ring R b1 , ring R b2 , ring R b3 , ring R b4 and ring R b5 The examples and preferred ranges are the same as those of the above. Examples and preferred ranges of the divalent or higher valent group which may have a substituent in formula (b1-2-0) are the same as the examples and preferred ranges of the divalent or higher valent group which may have a substituent in formula (BM-1).

[0374] The fused ring compound represented by formula (b1-2-0) is preferably a fused ring compound represented by formula (BM-2) because the external quantum efficiency of the light-emitting device is even more excellent.

[0375] [ka] [In the formula, ring R b1 , ring R b2 , ring R b3 , ring R b4 , ring R b5 , X b2 , X b4 , ring R Xb1 and ring R Xb2 has the same meaning as above. Ring R b1 , ring R b2 , ring R b3 , ring R b4 , ring R b5 , ring R Xb1 , ring R Xb2 , X b1 , X b2 , X b3 and X b4 At least one of them has a polymerizable group.]

[0376] In particular, the fused ring compound represented by formula (BM-2) is preferably a fused ring compound represented by the following formula (1M).

[0377] [ka] [Wherein Z and X 1 represents the same meaning as above. Multiple Zs and Xs 1 At least one of them has a polymerizable group.]

[0378] An example of the fused ring compound is a compound represented by the above formula (1) substituted with at least one polymerizable group.

[0379] The polymerizable group is preferably at least one selected from the group consisting of Substituent Group A and Substituent Group B. The number of polymerizable groups is preferably 1 to 6, more preferably 2 to 5, still more preferably 2 or 3, and particularly preferably 2.

[0380] In the method for producing a polymer compound according to the present disclosure, the compound having a polymerizable group may contain a compound other than a fused ring compound, i.e., the fused ring compound may be polymerized with another compound. Examples of other compounds include polymerizable compounds based on the structural unit represented by the above formula (X) and polymerizable compounds based on the structural unit represented by the above formula (Y).

[0381] The content of the fused ring compound in the compound having a polymerizable group is preferably 0.01 to 50 mol %, more preferably 0.05 to 10 mol %, even more preferably 0.1 to 5 mol %, and particularly preferably 0.2 to 3 mol %.

[0382] (Polymerization process) The method for producing a polymer compound according to the present disclosure includes a step of polymerizing a compound having a polymerizable group in the presence of a transition metal catalyst and an inorganic base (hereinafter also referred to as the "polymerization step"). The polymerization step is carried out, for example, by utilizing a Suzuki coupling reaction. Examples of the polymerizable group include a substituent represented by the Substituent Group A and a substituent represented by the Substituent Group B. When there is one type of compound having a polymerizable group, it is preferable that the compound having a polymerizable group has one or more substituents represented by the Substituent Group A and one or more substituents represented by the Substituent Group B. When there are two or more types of compounds having a polymerizable group, it is preferable that the compound having a polymerizable group has two or more substituents represented by the Substituent Group A and two or more substituents represented by the Substituent Group B.

[0383] One embodiment of the method for producing a polymer compound of the present disclosure includes, for example, a method of polymerizing a compound represented by formula (U-1) and / or a compound represented by formula (U-2) with a compound in which two hydrogen atoms of a structural unit represented by formula (1) are substituted with groups selected from Substituent Group A and Substituent Group B, in the presence of a transition metal catalyst, an inorganic base, and a solvent, using a Suzuki coupling reaction, to obtain a polymer compound having a structural unit represented by formula (T-1) and / or a structural unit represented by formula (T-2), and a structural unit represented by formula (1). In the method for producing a polymer compound of the present disclosure, for example, a compound represented by formula (M-1) may be used as the compound represented by formula (U-1), a compound represented by formula (M-2) may be used as the compound represented by formula (U-2), and a compound in which two hydrogen atoms of the constitutional unit represented by formula (1) have been substituted with groups selected from Substituent Group A and Substituent Group B may be used as a compound represented by formula (M-3) and / or a compound represented by formula (M-4).

[0384] JPEG2025129031000129.jpg52164 [In the formula, Ar a1 , Ar a2 , Ar a3 , Ar b1 , Ar b2 and Ar b3 each independently represents a divalent aromatic hydrocarbon group, a divalent heterocyclic group, or a divalent group in which two or more groups selected from divalent aromatic hydrocarbon groups and divalent heterocyclic groups are linked directly or via a linking group, and these groups may have a substituent; Ar a2 , Ar a3 , Ar b2 and Ar b3 When there are a plurality of each of the groups, they may be the same or different. R a1 , R a2 , R b1 and R b2 each independently represents an alkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent; R a1 , R a2 , Rb1 and R b2 When there are a plurality of each of the groups, they may be the same or different. a1 and b1 each independently represent 0, 1 or 2. a2 and b2 each independently represent 0 or 1, and when a plurality of a2's and b2's are present, they may be the same or different. Z 1 , Z 2 , Z 3 and Z 4 each independently represents a group or atom selected from Substituent Group A and Substituent Group B.

[0385] [ka] [In the formula, Ar a1 , Ar a2 , Ar a3 , Ar b1 , Ar b2 , R a1 , R a2 , R b1 , R b2 , a1, a2, b1 and b2 have the same meanings as above.]

[0386] Z 1 , Z 2 , Z 3 and Z 4 Examples and preferred ranges of Z C1 , Z C2 , Z C3 and Z C4 The examples and preferred ranges are the same as those of Z 1 , Z 2 , Z 3 and Z 4 Among these, it is preferred that at least one of them is a group or atom selected from the substituent group A and at least one of them is a group selected from the substituent group B; 1 , Z 2 , Z 3 and Z 4Among these, it is more preferable that two groups are groups or atoms selected from the substituent group A, and the other two groups are groups or atoms selected from the substituent group B. Among them, Z 1 and Z 2 is a group or atom selected from the substituent group A, and Z 3 and Z 4 is more preferably a group or atom selected from the substituent group B. 1 and Z 2 is a group or atom selected from the substituent group B, and Z 3 and Z 4 is more preferably a group or atom selected from the substituent group A.

[0387] In the polymerization reaction, it is preferable to reduce the oxygen concentration in the reaction vessel by replacing the atmosphere with an inert gas, preferably to less than 0.2%, more preferably less than 0.05%.

[0388] In the polymerization reaction, the reaction temperature is usually from -100°C to 200°C, preferably from 0°C to 150°C, and more preferably from 60°C to 120°C.

[0389] In the polymerization reaction, the reaction time is usually 0.1 hour or more, preferably 0.5 hour or more, and more preferably 1 hour or more.

[0390] In the method for producing a polymer compound according to the present disclosure, the compound represented by formula (U-1), the compound represented by formula (U-2), and the compound in which two hydrogen atoms of the constitutional unit represented by formula (1) have been substituted with groups selected from Substituent Group A or Substituent Group B may each be used alone or in combination of two or more.

[0391] Examples of the transition metal catalyst include nickel phosphine complexes, combinations of nickel compounds and phosphine compounds, palladium phosphine complexes, and combinations of palladium compounds and phosphine compounds.

[0392] Examples of nickel phosphine complexes include dichlorobis(triphenylphosphine)nickel(II) and dichlorobis(tricyclohexylphosphine)nickel(II).

[0393] Examples of combinations of nickel compounds and phosphine compounds include combinations of nickel compounds such as bis(cyclooctadiene)nickel(0) and nickel(II) chloride with phosphine compounds such as triphenylphosphine, tricyclohexylphosphine and 1,1'-bis(diphenylphosphino)ferrocene.

[0394] Examples of palladium phosphine complexes include triarylphosphine palladium complexes such as tetrakis(triphenylphosphine)palladium(0), dichlorobis(triphenylphosphine)palladium(II), dichlorobis(tri-o-tolylphosphine)palladium(II), dichlorobis(tri-o-methoxyphenylphosphine)palladium(II), and dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II); alkyldiarylphosphine palladium complexes such as dichlorobis(methyldiphenylphosphine)palladium(II); and dichlorobis(2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenylphosphine). dialkylarylphosphine palladium complexes such as (2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)palladium(II), dichloro[di-tert-butyl(p-dimethylaminophenyl)]palladium(II), (2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)palladium(II) methanesulfonate and dichlorobis(dicyclopentyl-o-methoxyphenylphosphine)palladium(II); and trialkylphosphine palladium complexes such as bis(tri-tert-butylphosphine)palladium(0) and dichlorobis(tricyclohexylphosphine)palladium(II).

[0395] Examples of combinations of palladium compounds and phosphine compounds include palladium compounds such as tris(dibenzylideneacetone)dipalladium(0), palladium(II) acetate, and palladium(II) chloride, and triarylphosphine compounds such as tri-o-tolylphosphine, tri-o-methoxyphenylphosphine, and 1,1'-bis(diphenylphosphino)ferrocene, alkyldiarylphosphine compounds such as methyldiphenylphosphine, 2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, and 2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl. and combinations with dialkylarylphosphine compounds such as 2-(di-tert-butylphosphino)-2',4',6'-triisopropyl-1,1'-biphenyl, 2-(di-tert-butylphosphino)-1-phenylindole, and 2-(di-tert-butylphosphino)-1-phenyl-1H-pyrrole; and combinations with trialkylphosphine compounds such as tri-tert-butylphosphine, tri-tert-butylphosphonium tetrafluoroborate, tricyclohexylphosphine, and di(1-adamantyl)-n-butylphosphine.

[0396] The transition metal catalyst is preferably a palladium complex or a combination of a palladium compound and a phosphine compound, more preferably a divalent palladium complex or a combination of a divalent palladium compound and a phosphine compound.

[0397] Among the palladium complexes, triarylphosphine palladium complexes, alkyldiarylphosphine palladium complexes, dialkylarylphosphine palladium complexes and trialkylphosphine palladium complexes are preferred, and triarylphosphine palladium complexes and dialkylarylphosphine palladium complexes are more preferred.

[0398] Among the phosphine compounds, triarylphosphine compounds, alkyldiarylphosphine compounds, dialkylarylphosphine compounds and trialkylphosphine compounds are preferred, and triarylphosphine compounds and dialkylarylphosphine compounds are more preferred.

[0399] The transition metal catalyst may be a homogeneous complex catalyst or a heterogeneous complex catalyst, and is preferably a homogeneous complex catalyst.

[0400] The amount of the transition metal catalyst used is usually 0.00001 to 1 molar equivalent in terms of the amount of metal relative to the total number of moles of the raw material monomers.

[0401] Examples of inorganic bases include sodium carbonate, potassium carbonate, cesium carbonate, potassium fluoride, cesium fluoride, tripotassium phosphate, etc., with sodium carbonate, potassium carbonate, and tripotassium phosphate being preferred, and tripotassium phosphate being more preferred. Each of the bases may be used alone or in combination of two or more.

[0402] The amount of the base used is usually 4 to 100 molar equivalents relative to the total number of moles of the raw material monomers.

[0403] Examples of the solvent include chlorinated hydrocarbon solvents such as 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, and o-dichlorobenzene; ether solvents such as tetrahydrofuran, dioxane, anisole, dimethoxybenzene, and 4-methylanisole; aromatic hydrocarbon solvents such as toluene, xylene, mesitylene, ethylbenzene, n-hexylbenzene, decylbenzene, and cyclohexylbenzene; cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane, n-dodecane, and bismuth. Examples of suitable solvents include aliphatic hydrocarbon solvents such as hexane and the like; ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone, and acetophenone; ester solvents such as ethyl acetate, butyl acetate, ethyl cellosolve acetate, methyl benzoate, and phenyl acetate; polyhydric alcohol solvents such as ethylene glycol, glycerin, and 1,2-hexanediol; alcohol solvents such as methanol, ethanol, isopropyl alcohol, and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; and water. These solvents may be used alone or in combination of two or more. The solvent is preferably a combination of one or more organic solvents and water.

[0404] The ratio of the total volume of one or more organic solvents to the volume of water is preferably 1 / 2 or more, more preferably 1 or more, even more preferably 2 or more, and particularly preferably 4 or more. At least one solvent is preferably a hydrophobic organic solvent, more preferably a chlorinated hydrocarbon solvent, an aromatic hydrocarbon solvent or an aliphatic hydrocarbon solvent, and even more preferably an aromatic hydrocarbon solvent.

[0405] The amount of the solvent used is usually 10 parts by mass to 100 parts by mass of the total of the raw material monomers. The amount is 100,000 parts by mass, preferably 30 to 30,000 parts by mass, and more preferably 100 to 10,000 parts by mass.

[0406] In the polymerization reaction, a phase transfer catalyst may be further used. Examples of the phase transfer catalyst include tetrabutylammonium chloride, tetrabutylammonium bromide, and methyltri-n-octylammonium chloride. Each of the phase transfer catalysts may be used alone or in combination of two or more.

[0407] The amount of 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.

[0408] The substituent group A is preferably a chlorine atom or a bromine atom, more preferably a bromine atom.

[0409] The substituent group B is preferably a boronic acid ester residue, more preferably a group represented by formula (G-1) to formula (G-10), and further preferably a group represented by formula (G-4) and formula (G-6) to formula (G-10).

[0410] Z 1 and Z 2 is selected from the substituent group A, Z 3 and Z 4 is preferably selected from the substituent group B.

[0411] [ka]

[0412] Examples of the compound represented by formula (U-1) include compounds represented by formulas (J-1) to (J-22), and preferred are compounds represented by formulas (J-1) to (J-3), (J-5) to (J-10), and (J-15) to (J-22).

[0413] [ka]

[0414] [ka]

[0415] [ka]

[0416] [ka] [In the formula, R has the same meaning as above.]

[0417] Examples of the compound represented by formula (U-2) include compounds represented by formulas (K-1) to (K-13), and the compounds represented by formulas (K-1) to (K-3), (K-5) to (K-9), and (K-13) are preferred.

[0418] [ka]

[0419] [ka]

[0420] [ka] [In the formula, R has the same meaning as above.]

[0421] In the polymerization reaction, "other compounds" other than the compound represented by formula (U-1) and the compound represented by formula (U-2) may also be polymerized.

[0422] Examples of the "other compounds" include compounds represented by formulas (L-1) to (L-8), preferably compounds represented by formulas (L-1) to (L-3) and formulas (L-5) to (L-7), and more preferably compounds represented by formulas (L-1) to (L-3).

[0423] [ka] [In the formula, R has the same meaning as above.]

[0424] (Post-processing process) In the method for producing a polymer compound according to the present disclosure, post-treatment of the polymerization reaction may be carried out, if necessary, by purification using methods such as liquid separation, dehydration, recrystallization, reprecipitation, column chromatography, and Soxhlet washing.

[0425] The separation step is a step in which water is added to a solution containing a polymer compound and a solvent, the mixture is stirred, and the mixture is allowed to stand to separate into an organic solvent layer and an aqueous layer, and the aqueous layer is then removed. The water may contain an acidic compound such as hydrogen chloride or acetic acid, a basic compound such as ammonia or sodium carbonate, a neutral compound such as sodium chloride, or a metal capture agent such as sodium diethyldithiocarbamate. The mass of the additive is preferably 1% to 20%, more preferably 3% to 10%, of the mass of water. Water-soluble impurities can be removed in the separation step.

[0426] The dehydration step is a step of removing water from a solution containing a polymer compound and a solvent. As a dehydration method, a desiccant such as magnesium sulfate or sodium sulfate may be added and stirred, and then the desiccant may be filtered off, or the solution containing a polymer compound and a solvent may be azeotropically dehydrated. When the production scale is large, dehydration by azeotropic dehydration is preferred.

[0427] The column chromatography step is a step of removing impurities by passing a mixture containing a polymer compound and a solvent through a column packed with an adsorbent. Examples of the adsorbent that can be used include alumina, silica gel, zeolite, and ion exchange resin, and among these, alumina is preferably used.

[0428] In order to extract the polymer compound from the solution containing the polymer compound and the solvent, it is preferable to include a reprecipitation step, a filtration step, and a drying step.

[0429] The reprecipitation step is a step in which a solution containing a polymer compound and a solvent is mixed with a poor solvent to precipitate the polymer compound. A poor solvent is a solvent in which the solubility of a polymer compound at 20°C is less than 1 g (polymer compound) / 100 g (poor solvent). Examples of poor solvents include amide solvents such as N,N-dimethylacetamide and N,N-dimethylformamide; alcohol solvents such as methanol, ethanol, isopropanol, ethylene glycol, isopropyl alcohol and propylene glycol; nitrile solvents such as acetonitrile; ester solvents such as methyl acetate and ethyl acetate, etc. Among these, alcohol solvents are preferred, with methanol, ethanol and isopropanol being more preferred, and methanol being even more preferred.

[0430] The filtration step is a step in which a composition containing a solid polymer compound and a solvent is passed through a porous filter medium to separate solid polymer compounds that are larger than the holes from the solvent.

[0431] The drying step is a step of removing water and solvent from a polymer compound containing water and solvent. [Example]

[0432] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.

[0433] 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:

[0434] <Measurement conditions> The polymer compound to be measured was dissolved in tetrahydrofuran at a concentration of approximately 0.05% by mass, and 10 μL of the solution was injected into the SEC. The mobile phase was run at a flow rate of 0.6 mL / min. The columns used were a TSKguardcolumn SuperAW-H, a TSKgel Super AWM-H, and a TSKgel SuperAW3000 (all manufactured by Tosoh) connected in series. A UV-VIS detector (manufactured by Tosoh, product name: UV-8320GPC) was used as the detector.

[0435] High-performance liquid chromatography (HPLC) area percentage values ​​were used as an index of compound purity. Unless otherwise specified, these values ​​were measured at UV = 254 nm using an HPLC (Shimadzu Corporation, product name: LC-20A). The compounds to be measured were dissolved in tetrahydrofuran or chloroform to a concentration of 0.01 to 0.2% by mass, and 1 to 10 μL was injected into the HPLC depending on the concentration. The HPLC mobile phase was a mixture of acetonitrile and tetrahydrofuran, varying in volume ratio from 100 / 0 to 0 / 100, at a flow rate of 1.0 mL / min. The column used was a SUMIPAX ODS Z-CLUE (Sumika Chemical Analysis Center, inner diameter: 4.6 mm, length: 250 mm, particle size: 3 μm) or an ODS column with equivalent performance. A photodiode array detector (Shimadzu Corporation, product name: SPD-M20A) was used as the detector.

[0436] <Synthesis of Compound S1> Compounds S1 and S2 were synthesized by the following method.

[0437] [ka]

[0438] Compound S1 is hereinafter also referred to as compound S-E1. Compound S2 is hereinafter also referred to as compound S-EC1.

[0439] After purging the reaction vessel with nitrogen, 1-bromo-3-chloro-5-(1,1'-dimethylethyl)benzene (83.7 g, 338 mmol), 3-tert-butylaniline (53.0 g, 355 mmol), sodium tert-butoxide (65.0 g, 676 mmol), toluene (1060 mL), tris(dibenzylideneacetone)dipalladium(0) (6.3 g, 11 mmol), and tri-tert-butylphosphonium tetrafluoroborate (6.2 g, 21 mmol) were added and stirred at 55°C for 6 hours. After cooling to room temperature (25±5°C, the same applies below), water was added and stirred at room temperature. The aqueous layer was separated. The resulting organic layer was dried over magnesium sulfate and filtered. Activated carbon was added to the filtrate, which was stirred for 1 hour, then filtered through a filter pad with Celite. The filtrate was concentrated to obtain the crude product. The resulting crude product was purified by silica gel column chromatography (hexane and toluene mixed solvent) and dried under reduced pressure at 50°C to obtain compound S1a (97.4 g, transparent oil). The HPLC area percentage value of compound S1a was 99.6%. 1 H NMR (400MHz, CDCl3) δ(ppm)=7.23(d,1H),7.12(t,1H),7.02(m,1H),6.95-6.85(m,4H),5.72(br,1H),1.31(s,9H),1.28(s,9H).

[0440] After purging the reaction vessel with nitrogen, 1,2,3-tribromobenzene (45.4 g, 144 mmol), compound S1a (93.3 g, 295 mmol), and toluene (907 mL) were added. Sodium tert-butoxide (41.6 g, 432 mmol), tris(dibenzylideneacetone)dipalladium(0) (6.6 g, 7 mmol), and tri-tert-butylphosphonium tetrafluoroborate (4.4 g, 15 mmol) were added and stirred at 85 °C for 3 hours. After cooling to room temperature, toluene and silica gel were added, followed by stirring and filtration through a filter padded with silica gel. Activated carbon was added to the filtrate, which was stirred for 1 hour, then filtered through a filter padded with Celite. The filtrate was concentrated to obtain the crude product. The crude product was purified by silica gel column chromatography (hexane and toluene mixed solvent). The resulting mixture was recrystallized using ethyl acetate and methanol, and then dried under reduced pressure at 50° C. to obtain Compound S1b (69.1 g, white solid). The HPLC area percentage value of Compound S1b was 99.2%. 1 H NMR (400MHz, CDCl3) δ(ppm)=7.36(dd,1H),7.20-7.10(m,6H),7.03(m,2H),6.89(m,4H),6.75(m,2H),6.68(t,2H),1.24(s,18H),1.20(s,18H).

[0441] After the reaction vessel was purged with nitrogen, compound S1b (32.0 g, 40.8 mmol) and xylene (1280 mL) were added. The mixture was cooled to -50 °C in a dry ice acetone bath, and n-butyllithium (29.6 mL, 45 mmol, 1.52 M hexane solution) was added dropwise. The mixture was stirred at 0 °C for 2 hours and at room temperature for 3 hours. The mixture was again cooled to -50 °C in a dry ice acetone bath, and boron tribromide (20.3 g, 82 mmol) was added. The mixture was stirred at 100 °C for 5 hours. After cooling the reaction mixture, diisopropylethylamine and a 10% by weight aqueous solution of sodium sulfite were added and stirred for 30 minutes. The aqueous layer was separated. The resulting organic layer was dried over magnesium sulfate and filtered through a filter lined with Florisil and silica gel. The filtrate was concentrated to obtain the crude product. The resulting crude product was purified by silica gel column chromatography (hexane and toluene mixed solvent). The resulting mixture was recrystallized using tetrahydrofuran and methanol, and then dried under reduced pressure at 50° C. to obtain Compound S1c (24.3 g, yellow-green solid). The HPLC area percentage value of Compound S1c was 98.3%. 1 H NMR (400MHz, CDCl3) δ(ppm)=8.87(d,2H),7.59(t,2H),7.35-7.13(m,7H),6.69(d,2H),6.18(d,2H),1.36(s,18H),1.24(s,18H).

[0442] After the reaction vessel was purged with nitrogen, 1,3-dimethyl-2-bromobenzene (16.8 g, 139 mmol), p-toluidine (15.0 g, 140 mmol), and toluene (345 mL) were added. mol), tris(dibenzylideneacetone)dipalladium(0) (1.3 g, 2 mmol), and tri-tert-butylphosphonium tetrafluoroborate (1.3 g, 4 mmol) were added and stirred at 80 °C for 2 hours. After cooling to room temperature, water was added and the mixture was stirred at room temperature, and the aqueous layer was separated. The resulting organic layer was washed with water, dried over magnesium sulfate, and filtered. The filtrate was concentrated to obtain a crude product. The resulting crude product was purified by silica gel column chromatography (hexane and ethyl acetate mixed solvent) and dried under reduced pressure at 50 °C to obtain compound S1d (918.3 g, light brown oil). The HPLC area percentage value of compound S1d was 99.5% or higher. 1 H-NMR (400MHz, CDCl3)δ(ppm)=7.21-7.11(m,3H),7.04(d, 2H), 6.50(d, 2H), 2.32(s, 3H), 2.28(s, 6H).

[0443] After the reaction vessel was purged with nitrogen, compound S1c (18.0 g, 25 mmol), compound S1d (10.9 g, 52 mmol), and toluene (540 mL) were added. Sodium tert-butoxide (10.9 g, 114 mmol), palladium acetate (170 mg, 0.8 mmol), and 2-dicyclohexylphosphino-2',6'-diisopropoxybiphenyl (706 mg, 1.5 mmol) were added and stirred at 110 °C for 2 hours. After cooling to room temperature, toluene and silica gel were added, and the mixture was stirred for 15 minutes and then filtered through a filter lined with silica gel. Activated carbon was added to the filtrate, which was stirred for 1 hour, and then filtered through a filter lined with Celite. The filtrate was concentrated to obtain a crude product. The obtained crude product was purified by silica gel column chromatography (mixed solvent of hexane and toluene), and the obtained solid was washed with methanol and dried under reduced pressure at 50 °C to obtain compound S1e (21.0 g, yellow solid). The HPLC area percentage value of compound S1e was 99.5% or more. 1H-NMR(400MHz, CDCl3)δ(ppm)=8.79(d,2H),7.37(t, 1H), 7.21-6.80(m, 22H), 6.70(d, 2H), 6.35(d, 2H),2.20(s, 6H), 2.10(s,12H)1.29(s, 18H),1.25(s,18H),1.23(s,18H).

[0444] After the reaction vessel was purged with nitrogen, compound S1e (11.0 g, 10 mmol) and chlorobenzene (275 mL) were added. Boron triiodide (39.6 g, 100 mmol) and 2,6-di-tert-butylpyridine (9.5 g, 50 mmol) were added and stirred at 70 °C for 4 hours. After cooling to 0 °C, a phosphate buffer solution (pH 6.8) was added and stirred for 30 minutes, after which the organic layer was separated. Water and toluene were added to the resulting organic layer and stirred for 15 minutes, after which the organic layer was separated. The resulting organic layer was washed with water, dried over magnesium sulfate, and filtered through a filter lined with silica gel. Methanol was added to the resulting filtrate, and the precipitated solid was filtered. The resulting solid was recrystallized from a mixed solvent of tetrahydrofuran and ethanol, and the resulting crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene). The resulting solid was recrystallized from a mixed solvent of tetrahydrofuran and ethanol and dried under reduced pressure at 50° C. to obtain compound S2 (1.8 g, orange solid). The HPLC area percentage value of compound S1d was 98.4%. 1 H-NMR (400MHz, CD2Cl2)δ(ppm)=10.44(s,1H),8.78(s,2H),8.64(d,2H),8.37(s,2H),7.70(s,2H),7.56(dd,2H), 7.45-7.34(m,8H),6.72(d,2H),6.37(d,2H),2.46(s,6H),2.08(s,6H),1.85(s,6H),1.35(s,18H),1.17(s,18H).

[0445] After purging the reaction vessel with a nitrogen atmosphere, compound S2 (1.3 g, 1.2 mmol), bis(pinacolato)diboron (0.9 g, 3.6 mmol), 4,4'-di-tert-butyl-2,2'-bipyridyl (26 mg, 0.1 mmol), and cyclopentyl methyl ether (65 mL) were added. Bis(1,5-cyclooctadiene)di-μ-methoxydiiridium(I) (64 mg, 0.05 mmol) was added and stirred at 80 °C for 6 hours. The reaction mass, cooled to room temperature, was added to a vessel containing methanol and cyclopentyl methyl ether and cooled to 0 °C. The mixture was stirred for 1 hour, and the resulting solid was filtered. The resulting solid was dissolved in toluene, activated clay was added, and the mixture was stirred for 30 minutes. The mixture was then filtered through a filter lined with silica gel and Celite, and the resulting filtrate was concentrated. The resulting crude product was washed with acetonitrile, and the resulting solid was recrystallized using a mixed solvent of toluene and acetonitrile. The resulting solid was purified by recycling GPC, recrystallized using a mixed solvent of toluene and acetonitrile, and dried under reduced pressure at 50°C to obtain compound S1 (770 mg, orange solid). The HPLC area percentage value of compound S1 was 99.5% or more. 1 H-NMR(400MHz, CD2Cl2)δ(ppm)=10.43(s,1H),8.77(s,2H),8.64(d,2H),8.36(s,2H),7.82(s,2H),7.77(s,2H),7.71(s,2H),7.56 (d,2H),7.33(d,2H),6.66(d,2H),6.40(s,2H),2.45(s,6H),2.09(s,6H),1.86(s,6H),1.40(s,24H),1.36(s,18H),1.17(s,18H).

[0446] <Synthesis of Compound P1> [ka] Compound S3 used was synthesized according to the method described in JP 2010 / 189630 A. Compounds S4 and S5 used were synthesized according to the method described in WO 2013 / 191088. After creating an inert gas atmosphere in the reaction vessel, compound S1 (0.042 g, 0.03 mmol), compound S3 (0.754 g, 1.51 mmol), compound S4 (0.701 g, 0.82 mmol), compound S5 (0.640 g, 0.76 mmol), palladium acetate (1.0 mg), tris-o-methoxyphenylphosphine (1.4 mg), 20% by mass tetraethylammonium hydroxide aqueous solution (21.5 g), and toluene (55 g) were added and stirred under reflux for 7 hours. Next, phenylboronic acid (77.0 mg) was added and stirred under reflux for 9 hours. Next, a sodium diethyldithiocarbamate aqueous solution was added and stirred at 40 °C for 1 hour. The oil layer was separated from the aqueous layer, washed with water and 3% by mass acetic acid water, and then passed through an alumina column and a silica gel column. The resulting oil layer was added dropwise to methanol to obtain a precipitate. The precipitate was filtered, washed with methanol, and dried under reduced pressure to obtain a number average molecular weight of Mn=6.8×10 4 , weight average molecular weight Mw=3.7×10 5 Compound P1 was obtained. Compound P1 is a copolymer composed of a structural unit derived from compound S1, a structural unit derived from compound S3, a structural unit derived from compound S4, and a structural unit derived from compound S5 in a molar ratio of 1:49:26:24.

[0447] <Synthesis of Compound P2> [ka] Compound P2 was synthesized according to the method described in JP 2012-036388 A. Compound P2 is a copolymer composed of a structural unit derived from compound S3, a structural unit derived from compound S4, and a structural unit derived from compound S5 in a molar ratio of 50:26:24.

[0448] Compound P2 is also referred to hereafter as compound S-H1. <Synthesis of Compound S-E2> Compound S-E2 was synthesized by the following method.

[0449] [ka]

[0450] After purging the reaction vessel with a nitrogen atmosphere, 3,5-dichloroaniline (112.9 g, 697 mmol), 3-tert-butylbromobenzene (135.0 g, 633 mmol), sodium tert-butoxide (121.8 g, 1267 mmol), toluene (3100 mL), tris(dibenzylideneacetone)dipalladium(0) (6.0 g, 10 mmol), and di-tert-butylphenylphosphine (4.5 g, 20 mmol) were added and stirred at 50°C for 3 hours and at 60°C for 5 hours. After cooling to room temperature, water was added and stirred at room temperature. The aqueous layer was separated. The resulting organic layer was dried over magnesium sulfate and filtered. Activated carbon was added to the filtrate, which was stirred for 1 hour, and then filtered through a filter pad with Celite. The filtrate was concentrated to obtain the crude product. The resulting crude product was purified by silica gel column chromatography (hexane and toluene mixed solvent) and dried under reduced pressure at 50 °C to obtain compound S-E2a (165.4 g, dark brown oil). The HPLC area percentage value of compound S-E2a was 98.5%. 1 H-NMR (400MHz, CD2Cl2): δ(ppm)=7.24(1H,t),7.12-7.06(2H,m),6.98-6.91(1H,m),6.85(2H,d),6.79(1H,t),5.86(1H,broad-s),1.29(9H,m). TLC-MS (positive): m / z = 294 [M+H] +

[0451] After purging the reaction vessel with nitrogen, 1,2,3-tribromobenzene (86.1 g, 273 mmol), compound S-E2a (148.8 g, 506 mmol), and toluene (2976 mL) were added. Sodium tert-butoxide (157.7 g, 1641 mmol), tris(dibenzylideneacetone)dipalladium(0) (19.4 g, 33 mmol), and tri-tert-butylphosphonium tetrafluoroborate (19.0 g, 66 mmol) were added and stirred at 80 °C for 6 hours. After cooling to room temperature, water was added and stirred at room temperature. The aqueous layer was separated. The resulting organic layer was dried over magnesium sulfate and filtered. Activated carbon was added to the filtrate, which was stirred for 1 hour. The filtrate was then filtered through a filter pad with Celite. The filtrate was concentrated to obtain the crude product. The crude product was purified by silica gel column chromatography (a mixed solvent of heptane and toluene). The compound S-E2b (105.2 g, white solid) was obtained by recrystallization using heptane and ethanol and drying under reduced pressure at 50° C. The HPLC area percentage value of the compound S-E2b was 99.4%. 1 H-NMR (400MHz, CD2Cl2): δ(ppm)=7.40(1H,t),7.25-7.17(4H,m),7.16-7.10(4H,m),6.90-6.86(2H,m),6.84(2H,t),6.68(4H,d),1.20(18H,s). TLC-MS (positive): m / z = 739 [M+H] +

[0452] After the reaction vessel was purged with nitrogen, compound S-E2b (95.0 g, 128 mmol) and toluene (1900 mL) were added. In an ice bath, n-butyllithium (123 mL, 192 mmol, 1.56 M hexane solution) was added dropwise and stirred at 0°C for 4 hours. The mixture was cooled to -20°C in a dry ice acetone bath, and boron tribromide (96.3 g, 384 mmol) was added. The mixture was stirred at 50°C for 3 hours. After cooling the reaction mixture, diisopropylethylamine and 10% by weight aqueous sodium sulfite solution were added, and the mixture was stirred for 30 minutes. The aqueous layer was separated. The resulting organic layer was washed with 10% by weight aqueous sodium sulfite solution and water. The resulting organic layer was dried over magnesium sulfate and filtered through a filter lined with alumina and Celite. The filtrate was concentrated to obtain the crude product. The resulting crude product was washed with a mixed solvent of heptane and ethanol, recrystallized using toluene and acetonitrile, and dried under reduced pressure at 50°C to obtain compound S-E2c (38.2 g, yellow solid). The HPLC area percentage value of compound S-E2c was 99.5%. 1 H-NMR (400MHz, CD2Cl2): δ(ppm)=8.81(2H,d),7.65(2H,t),7.35(6H,d),7.29(1H,t),6.70(2H,d),6.14(2H,d),1.22(18H,s).

[0453] After purging the reaction vessel with a nitrogen atmosphere, compound S-E2c (17.3 g, 23 mmol), 4,4'-dimethyldiphenylamine (9.3 g, 47 mmol), and toluene (346 mL) were added. Sodium tert-butoxide (13.5 g, 141 mmol), palladium acetate (1.3 g, 6 mmol), and 2-dicyclohexylphosphino-2',6'-diisopropoxybiphenyl (4.6 g, 11 mmol) were added and stirred at 70 °C for 2 hours. After cooling to room temperature, toluene and silica gel were added and stirred for 1 hour. The mixture was then filtered through a Celite-lined filter, and the filtrate was concentrated to obtain the crude product. The crude product was purified by silica gel column chromatography (hexane and toluene mixed solvent). The resulting solid was recrystallized with toluene and acetonitrile. The resulting solid was dried under reduced pressure at 50 °C to obtain compound S-E2d (13.9 g, yellow-green solid). The HPLC area percentage value of compound S-E2d was 99.5%. 1 H-NMR (400MHz, CD2Cl2): δ(ppm)=8.72(2H,d),7.37(1H,t),7.29(2H,dd),7.12(2H,t), 7.10-7.00(16H,m),6.86(2H,d),6.80(4H,d),6.29(2H,d),2.21(12H,s),1.31(18H,s).

[0454] After the reaction vessel was purged with nitrogen, compound S-E2d (5.8 g, 6 mmol) and ortho-dichlorobenzene (580 mL) were added. Boron triiodide (18.3 g, 47 mmol) was added and stirred at 110 °C for 6 hours. After cooling to 0 °C, diisopropylethylamine was added and stirred for 15 minutes. 10% aqueous sodium sulfite solution was then added, and the resulting organic layer was separated. Water and toluene were added to the resulting organic layer, and the resulting organic layer was stirred for 15 minutes. The organic layer was then separated. The resulting organic layer was washed with water, dried over magnesium sulfate, and filtered through a filter lined with alumina and celite. The resulting filtrate was concentrated to obtain 14.8 g of crude product. The above procedure was repeated, and the resulting crude product was combined, acetonitrile was added, and the precipitated solid was filtered. The resulting solid was recrystallized from a mixed solvent of toluene and acetonitrile and dried under reduced pressure at 50°C to obtain compound S-E2e (8.2 g, orange solid). The HPLC area percentage value of compound S-E2e was 99.0%. 1 H-NMR (400MHz, CD2Cl2): δ(ppm)=10.40(1H,s),8.67(2H,s),8.63(2H,d),8.38(2H,d),7.66(2H,d),7.62-7.50(6H, m),7.42(2H,d),7.35(2H,dd),7.25-7.10(2H,m),6.80(2H,d),6.41(2H,d),2.56(6H,s),2.40(6H,s),1.38(18H,s).

[0455] After the reaction vessel was purged with nitrogen, compound S-E2e (4.0 g, 4.0 mmol), bis(pinacolato)diboron (6.0 g, 23.8 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.3 g, 0.5 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.4 g, 0.9 mmol), Silica-SMAP (1.4 g, 0.1 mmol), potassium iodide (3.9 g, 23.8 mmol), potassium acetate (4.7 g, 47.6 mmol), xylene (100 mL), and N-methyl-2-pyrrolidone (300 mL) were added. The mixture was stirred at 130°C for 3 hours. After cooling to room temperature, toluene and water were added and stirred, and the organic layer was separated. The resulting organic layer was washed with water, dried over magnesium sulfate, and filtered through a filter lined with silica gel and Celite. The filtrate was concentrated to obtain a crude product. The resulting crude product was recrystallized using a mixed solvent of toluene and acetonitrile and dried under reduced pressure at 50°C to obtain compound S-E2 (2.9 g, orange solid). The HPLC area percentage value of compound S-E2 was 99.1%. 1H-NMR(400MHz, CD2Cl2)δ(ppm)=10.42(s,1H), 8.70(d,2H),8.69(s,2H), 8.43(d,2H),8.14(s,2H), 7.63(br,4H),7.60(dd, 2H) ,7.49(br,2H), 7.34(dd,2H),7.60(dd,2H),7.27(br,2H),6.85(s,2H),6.75(d,2H),2.67(s,6H),2.42(s,6H),1.39(s,18H),1.28(s,24H).

[0456] <Synthesis of compound S-E3>

[0457] Compound S-E3 was synthesized by the following method.

[0458] [ka]

[0459] After purging the reaction vessel with a nitrogen atmosphere, 1-bromo-3-iodobenzene (135.0 g, 477 mmol), 3,5-dimethylphenylboronic acid (78.7 g, 525 mmol), tetrakistriphenylphosphine (16.5 g, 14 mmol), ethanol (1013 mL), toluene (2025 mL), and 16% aqueous sodium carbonate (1200 mL) were added and stirred at 65 °C for 13 hours. After cooling to room temperature, water was added and stirred at room temperature, and the aqueous layer was separated. The resulting organic layer was dried over magnesium sulfate, activated carbon was added, and the mixture was stirred for 1 hour. The mixture was then filtered through a Celite-lined filter, and the filtrate was concentrated to obtain the crude product. The resulting crude product was purified by silica gel column chromatography (hexane) and dried under reduced pressure at 50 °C to obtain compound S-E3a (150.7 g, clear oil). The HPLC area percentage of compound S-E3a was 91.9%. 1 H-NMR (400MHz, CDCl3) δ(ppm)=7.74(t,1H),7.53(d,1H),7.46(d,1H),7.35-7.29(m,1H),7.19(s,2H),7.03(s,1H),2.37(s,6H).

[0460] After purging the reaction vessel with a nitrogen atmosphere, 3,5-dichloroaniline (85.3 g, 527 mmol), compound S-E3a (125.0 g, 527 mmol), sodium tert-butoxide (92.0 g, 957 mmol), toluene (2900 mL), tris(dibenzylideneacetone)dipalladium(0) (13.2 g, 24 mmol), and di-tert-butylphenylphosphine (6.4 g, 29 mmol) were added and stirred at 60 °C for 7 hours. After cooling to room temperature, water was added and the mixture was stirred at room temperature. The aqueous layer was separated. The resulting organic layer was washed with water, dried over magnesium sulfate, added with activated carbon, and stirred for 1 hour. The mixture was then filtered through a filter pad with Celite and silica gel. The filtrate was concentrated to obtain the crude product. The resulting crude product was purified by silica gel column chromatography (hexane and toluene mixed solvent) and dried under reduced pressure at 50 °C. The above procedure was repeated to obtain compound S-E3b (218.5 g, white solid), whose HPLC area percentage was 98.6%. 1 H-NMR (400MHz, CD2Cl2) δ(ppm)=7.39(t,1H),7.30(m,2H),7.20(s,2H),7.10(dd,1H),7.02(s,1H),6.94(d,2H),6.86(m,1H),5.96(s,1H),2.37(s,6H). TLC-MS (positive): m / z = 342 [M+H] +

[0461] After purging the reaction vessel with a nitrogen atmosphere, 1,2,3-tribromobenzene (54.2 g, 172 mmol), compound S-E3b (109.0 g, 318 mmol), and toluene (2200 mL) were added. Sodium tert-butoxide (99.3 g, 1033 mmol), tris(dibenzylideneacetone)dipalladium(0) (18.9 g, 21 mmol), and tri-tert-butylphosphonium tetrafluoroborate (12.0 g, 41 mmol) were added and stirred at 75 °C for 2 hours. After cooling to room temperature, water was added and the mixture was stirred at room temperature. The aqueous layer was separated. The resulting organic layer was washed with water, dried over magnesium sulfate, and activated carbon was added. The mixture was stirred for 1 hour. The mixture was then filtered through a filter padded with Celite and silica gel. The filtrate was concentrated to obtain the crude product. The crude product was purified by silica gel column chromatography (a mixed solvent of heptane and toluene). The resulting solid was washed with heptane and ethanol, recrystallized with toluene and acetonitrile, and dried under reduced pressure at 50 ° C. The above procedure was repeated to obtain compound S-E3c (142.5 g, white solid). The HPLC area percentage value of compound S-E3c was 98.1%. 1 H-NMR (400MHz, CD2Cl2) δ(ppm)=7.42(t,1H),7.35-7.30(m,6H),7.22(d,2H),7.10(s,4H),7.00-6.97(m,4H),6.88(t,1H),6.75(d,4H),6.21(d,2H),2.32(s,12H).

[0462] After the reaction vessel was purged with nitrogen, compound S-E3c (59.8 g, 71 mmol) and xylene (2400 mL) were added. The mixture was cooled to -10 °C in a dry ice acetone bath, and n-butyllithium (71.0 mL, 107 mmol, 1.51 M hexane solution) was added dropwise and stirred at 0 °C for 3 hours. The mixture was again cooled to -35 °C in a dry ice acetone bath, and boron tribromide (89.4 g, 357 mmol) was added and stirred at 100 °C for 2 hours. After cooling the reaction mixture, diisopropylethylamine and a 10% by weight aqueous solution of sodium sulfite were added and stirred for 30 minutes, and the aqueous layer was separated. The resulting organic layer was washed with ion-exchanged water, dried over magnesium sulfate, and filtered through a filter lined with Celite and silica gel. The filtrate was concentrated to obtain the crude product. The resulting crude product was recrystallized using toluene and acetonitrile and dried under reduced pressure at 50°C to obtain compound S-E3d (41.4 g, yellow solid). The HPLC area percentage value of compound S-E3d was 99.5% or more. 1 H-NMR (400MHz, CD2Cl2) δ(ppm)=9.00(d,2H),7.68(m,2H),7.55(dd,2H),7.37(t,1H),7.15(s,4H),7.03(s,2H),6.94(d,2H),6.21(d,2H),2.40(s,12H).

[0463] After the reaction vessel was purged with nitrogen, compound S-E3d (11.7 g, 15 mmol), 4,4'-dimethyldiphenylamine (6.0 g, 31 mmol), and toluene (350 mL) were added. Sodium tert-butoxide (6.6 g, 69 mmol), palladium acetate (820 mg, 4 mmol), and 2-dicyclohexylphosphino-2',6'-diisopropoxybiphenyl (3.0 g, 7 mmol) were added and stirred at 70 °C for 2 hours. After cooling to room temperature, toluene and silica gel were added, and the mixture was stirred for 15 minutes and then filtered through a filter padded with silica gel. Activated carbon was added to the filtrate, which was stirred for 1 hour and then filtered through a filter padded with Celite. The filtrate was concentrated to obtain the crude product. The resulting crude product was purified by silica gel column chromatography (mixed solvent of hexane and toluene) 2, and the resulting solid was recrystallized from a mixed solvent of toluene and acetonitrile and dried under reduced pressure at 50 °C to obtain compound S-E3e (8.0 g, yellow solid). The HPLC area percentage value of compound S-E3e was 99.2%. 1 H-NMR (400MHz, CD2Cl2)δ(ppm)=8.92(d,2H),7.51-7.44(m,3H),7.24(s,4H),7.15(m,2H),7.12 (d,2H),7.10-7.05(m,18H),6.92(s,2H),6.86(s,2H),6.39(d,2H),2.44(s,12H),2.27(s,12H).

[0464] After the reaction vessel was purged with nitrogen, compound S-E3e (5.8 g, 5 mmol) and chlorobenzene (232 mL) were added. Boron triiodide (16.7 g, 43 mmol) and N,N'-dimethyl-ortho-toluidine (2.9 g, 21 mmol) were added and stirred at 130 °C for 2 hours. After cooling to 0 °C, diisopropylethylamine was added and stirred for 15 minutes. 10% aqueous sodium sulfite solution was then added and stirred for 30 minutes, after which the organic layer was separated. The resulting organic layer was washed with water, dried over magnesium sulfate, and filtered through a filter lined with silica gel and Celite. Acetonitrile was added to the filtrate, and the precipitated solid was filtered. The resulting solid was recrystallized in a mixed solvent of toluene and acetonitrile. The resulting solid was dissolved in toluene, activated clay was added, and the mixture was stirred for 30 minutes. The resulting filtrate was then filtered through a filter lined with Celite. The resulting filtrate was concentrated to obtain the crude product. The resulting crude product was recrystallized from a mixed solvent of toluene and acetonitrile and dried under reduced pressure at 50°C to obtain compound S-E3f (1.4 g, yellow solid). The HPLC area percentage value of compound S-E3f was 98.5%. 1 H-NMR(400MHz, CDCl3)δ(ppm)=10.47(s,1H),8.78(d,2H),8.72(s,2H),8.61(s,2H),7.88(s,2H),7.74(dd,2H),7.59-7.53(m,4H),7.54- 7.44(m,2H),7.36-7.35(m,2H),7.30-7.24(m,6H),7.02(s,2H),6.85-6.79(m,2H),6.48(d,2H),2.59(s,6H),2.45(s,6H),2.40(s,12H).

[0465] After the reaction vessel was purged with nitrogen, compound-E3f (1.3 g, 1.2 mmol), bis(pinacolato)diboron (3.7 g, 14.5 mmol), tris(dibenzylideneacetone)dipalladium(0) (89 mg, 0.2 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (126 mg, 0.3 mmol), Silica-SMAP (430 mg, 0.03 mmol), potassium iodide (1.2 g, 7.2 mmol), potassium acetate (1.4 g, 14.5 mmol), xylene (33 mL), and N-methyl-2-pyrrolidone (100 mL) were added and stirred at 120 °C for 3 hours. After cooling to room temperature, toluene and water were added and the mixture was stirred, and the organic layer was separated. The resulting organic layer was washed with water, dried over magnesium sulfate, and filtered through a filter lined with silica gel and Celite. The filtrate was concentrated to obtain a crude product. The crude product was recrystallized using a mixed solvent of toluene and acetonitrile and dried under reduced pressure at 50 °C to obtain compound S-E3 (950 mg, orange solid). The HPLC area percentage value of compound S-E3 was 99.5% or higher. 1H-NMR (400MHz, CD2Cl2)δ(ppm)=10.42(s,1H),8.85(d,2H),8.69(s,2H),8.59(s,2H),8.29(s,2H),7.78(dd,2H),7.96-7.60(br,4H),7.5 0-7.47(br,2H),7.36(dd,2H),7.30(s,6H),7.01(s,2H),6.92(s,2H),6.76(d,2H),2.63(s,6H),2.42(s,6H),2.36(s,12H),1.29(s,24H).

[0466] <Synthesis of Compound S-EC2>

[0467] Compound S-EC2 was synthesized by the following method.

[0468] [ka]

[0469] After the reaction vessel was purged with nitrogen, compound S-E2 (380 mg, 0.32 mmol), 2-bromo-9,9-dimethylfluorene (177 mg, 0.65 mmol), dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine (2 mg, 0.003 mmol), and toluene (23 mL) were mixed and heated to 90 °C. Then, aqueous sodium carbonate solution (a mixture of 1.5 g of sodium carbonate and 1 g of water) was added dropwise and stirred under reflux for 4 hours. After cooling the reaction mixture, 20 mL of toluene was added. The organic layer was separated, washed with water, dried over magnesium sulfate, and filtered. Activated carbon was added to the filtrate, which was stirred for 1 hour, then filtered through a filter padded with Celite. The filtrate was concentrated to obtain the crude product. The resulting crude product was washed with methanol, and the resulting solid was purified by recycled GPC. The resulting solid was recrystallized from a mixed solvent of toluene and acetonitrile. The resulting solid was washed with acetone, purified by silica gel column chromatography (a mixed solvent of hexane and toluene), recrystallized from a mixed solvent of toluene and acetonitrile, and dried under reduced pressure at 50°C to obtain compound S-EC2 (127 mg, orange solid). The HPLC area percentage value of compound S-EC2 was 99.5% or more. 1 H-NMR (400MHz, CD2Cl2)δ(ppm)=10.42(s,1H),8.73(s,2H),8.66(d,2H),8.55(s,2H),7.99(s,2H),7.71-7.67(m,4H),7.59-7 .56(m,8H),7.44-7.11(m,14H),6.87(d,2H),6.71(s,2H),2.56(s,6H),2.44(s,6H),1.44(s,6H),1.43(s,6H),1.38(s,18H).

[0470] <Synthesis of compound S-EC3>

[0471] Compound S-EC3 was synthesized by the following method.

[0472] [ka]

[0473] After the reaction vessel was purged with nitrogen, compound S-E2 (300 mg, 0.25 mmol), compound S-EC3a (297 mg, 0.56 mmol), triphenylphosphine (11 mg, 0.04 mmol), toluene (15 mL), 2-propanol (3 mL), and tetrakistriphenylphosphine palladium (35 mg, 0.03 mmol) were added and heated to 65 °C. Then, 9% aqueous tetraethylammonium solution (6.1 mL) was added dropwise and stirred at 65 °C for 4 hours. The reaction mixture was cooled, and the organic layer was separated. The organic layer was washed with water, dried over magnesium sulfate, and filtered. The filtrate was concentrated to obtain the crude product. The resulting crude product was recrystallized from a mixed solvent of toluene and acetonitrile, and the resulting solid was purified by recycled GPC. The resulting solid was recrystallized from a mixed solvent of toluene and heptane and dried under reduced pressure at 50°C to obtain compound S-EC3b (179 mg, red solid). The HPLC area percentage value of compound S-EC3b was 93.7%. 1 H-NMR(400MHz, CD2Cl2)δ(ppm)=10.55(s,1H),9.17(s,2H),8.86(d,2H),8.79(s,2H),8.63(d,4H),8.59(s,2H),8.49(d, 4H),8.03(d,2H),7.78(d,4H),7.77-7.62(m(overwrapped),8H),7.71(d,4H),7.68(d,4H),7.47(dd,2H),7.43(m,2 H),7.37(d,4H),7.08(d,2H),2.77(s,6H),2.71(t,4H),2.50(s,6H),1.70(m,4H),1.40-1.25(m,20H),1.30(s,18H), 0.91(t,6H).

[0474] After purging the reaction vessel with a nitrogen atmosphere, compound S-EC3b (50 mg, 0.03 mmol), 2-(9,9-di-n-octyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (29 mg, 0.06 mmol), tetrakistriphenylphosphine palladium (6 mg, 0.005 mmol), and toluene (5 mL) were added and heated to 70 °C. Then, aqueous sodium carbonate solution (a mixture of 36 mg of sodium carbonate and 2.5 g of water) was added dropwise and stirred at 70 °C for 6 hours. After cooling the reaction mixture, the organic layer was separated. The organic layer was washed with water, dried over magnesium sulfate, filtered, and the filtrate was concentrated to obtain the crude product. The crude product was purified by recycled GPC. The solid was washed with acetone and dried under reduced pressure at 50 °C to obtain compound S-EC3 (11 mg, red solid). The HPLC area percentage value of compound S-EC3 was 88.0%. 1 H-NMR (400MHz, CD2Cl2)δ(ppm)=10.57(s,1H),9.23(s, 2H),8.88(d,2H),8.81(s,2H),8.70(d,4H),8.68(d,4H), 8.64(s,2H),8.10(d,2H),7.89(d,4H),7.87(d,2H),7.82(d,4H),7.77-7.72(m(overwrapped),12H),7.69(d,4H), 7.70-7.65(m(overwrapped),2H),7.50-7.35(m,10H), 7.37(d,4H),7.09(d,2H),2.80(s,6H),2.71(t,4H),2.51(s,6H),2.10(m,8H),1.70(m,4H),1.40-1.25(m,28H), 1.30(s,18H),1.30-1.10(m,40H),0.91(t,6H),0.83(t, 6H),0.82(t,6H).

[0475] <Synthesis of Compound P-H2> [ka] Compound P-H2 was synthesized according to the method described in Advanced Materials, 2020, 32, 2004072.

[0476] Compound P-H2 is a copolymer composed of a structural unit derived from compound S3, a structural unit derived from compound S10, a structural unit derived from compound S18, and a structural unit derived from compound S11 in a molar ratio of 50:37:10:3.

[0477] <Synthesis of Compound P-E1> [ka] Compound S12 used was synthesized according to the method described in International Publication No. 2022 / 181075.

[0478] Compound P-E1 is a copolymer composed of a structural unit derived from compound S-E2, a structural unit derived from compound S3, and a structural unit derived from compound S12 in a molar ratio of 46.8:3.2:50.

[0479] After the reaction vessel was purged with an inert gas atmosphere, compound S-E2 (0.1866 g, 0.16 mmol), compound S3 (1.0061 g, 2.01 mmol), compound S12 (2.710 g, 2.46 mmol), dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine (1.8 mg), methyltri-n-octylammonium chloride (0.1979 g), 20% by mass potassium phosphate aqueous solution (20.0 g), and toluene (64 g) were added and stirred under reflux for 7 hours. Next, phenylboronic acid (0.2383 g) was added and stirred under reflux for 8 hours. Next, a sodium diethyldithiocarbamate aqueous solution was added and stirred at 40 °C for 15 minutes. The oil layer was separated from the aqueous layer, washed with ion-exchanged water, and then passed through an alumina column. The resulting oil layer was dropped into methanol to obtain a precipitate. The precipitate was filtered, washed with methanol, and dried under reduced pressure to obtain a number-average molecular weight Mn = 8.3 × 103 , weight average molecular weight Mw=2.2×10 5 Compound P-E1 was obtained.

[0480] Compound P-E1 is a copolymer containing structural units derived from compound S-E2, structural units derived from compound S3, and structural units derived from compound S12 in a molar ratio of 46.8:3.2:50, according to the theoretical value calculated from the amounts of the raw materials charged.

[0481] <Synthesis of Compound P-E2> [ka]

[0482] Compound P-E2 is a copolymer composed of a structural unit derived from compound S-E3, a structural unit derived from compound S3, and a structural unit derived from compound S12 in a molar ratio of 46.8:3.2:50.

[0483] Compound P-E2 was synthesized according to the method described for compound P-E1.

[0484] Compound P-E2 is a copolymer containing structural units derived from compound SS-E3, structural units derived from compound S3, and structural units derived from compound S12 in a molar ratio of 46.8:3.2:50, according to the theoretical value calculated from the amounts of the raw materials charged.

[0485] <Synthesis of Compound P-EC1> [ka]

[0486] Compound P-EC1 is a copolymer composed of a structural unit derived from compound S-E2, a structural unit derived from compound S3, and a structural unit derived from compound S12 in a molar ratio of 46.8:3.2:50.

[0487] After creating an inert gas atmosphere in the reaction vessel, compound S-E2 (0.1866 g, 0.16 mmol), compound S3 (1.0036 g, 2.01 mmol), compound S12 (2.710 g, 2.46 mmol), dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine (1.8 mg), 20% by mass tetraethylammonium hydroxide aqueous solution (20.0 g), and toluene (65 g) were added and stirred under reflux for 7 hours. Next, phenylboronic acid (0.2380 g) was added and stirred under reflux for 8 hours. Next, an aqueous solution of sodium diethyldithiacarbamate was added and stirred at 40 °C for 15 minutes. The oil layer was separated from the aqueous layer, washed with ion-exchanged water, and then passed through an alumina column. The resulting oil layer was added dropwise to methanol to obtain a precipitate. The precipitate was filtered, washed with methanol, and dried under reduced pressure to obtain a number average molecular weight of Mn=1.1×10 4 , weight average molecular weight Mw=2.7×10 5 Compound P-EC1 was obtained.

[0488] Compound P-E1 is a copolymer containing structural units derived from compound S-E2, structural units derived from compound S3, and structural units derived from compound S12 in a molar ratio of 46.8:3.2:50, according to the theoretical value calculated from the amounts of the raw materials charged.

[0489] <Synthesis of Compound P3> [ka]

[0490] Compound P3 is a copolymer composed of a structural unit derived from compound S3, a structural unit derived from compound S15, a structural unit derived from compound S13, a structural unit derived from compound S-E2, a structural unit derived from compound S14, and a structural unit derived from compound S12 in a molar ratio of 10.6:10:27.8:1.6:22.2:27.8.

[0491] Compound S15 used was synthesized according to the method described in International Publication No. 2013 / 146806. Compounds S13 and S14 used were synthesized according to the method described in S47380JP02.

[0492] Compound P3 was synthesized according to the method described for compound P1.

[0493] Compound P3 is a copolymer containing structural units derived from compound S3, structural units derived from compound S15, structural units derived from compound S13, structural units derived from compound S-E2, structural units derived from compound S14, and structural units derived from compound S12 in a molar ratio of 10.6:10:27.8:1.6:22.2:27.8, according to the theoretical value calculated from the amounts of the raw materials charged.

[0494] <Synthesis of Compound P-C1> Compound P-C1 used was synthesized according to the method described in JP-A-2022-013757.

[0495] [ka]

[0496] Compound P-C1 is a copolymer composed of a structural unit derived from compound S3, a structural unit derived from compound S-EC4, a structural unit derived from compound S4, and a structural unit derived from compound S5 in a molar ratio of 49:1:26:24.

[0497] <Synthesis of Compound P-C2> Compound P-C2 used was synthesized according to the method described in JP-A-2024-110226.

[0498] [ka]

[0499] Compound P-C2 is a copolymer composed of a structural unit derived from compound S3, a structural unit derived from compound S-EC5, a structural unit derived from compound S4, and a structural unit derived from compound S5 in a molar ratio of 49:1:26:24.

[0500] <Synthesis of Compound P-C3> Compound P-C3 used was synthesized according to the method described in JP-A-2024-110226.

[0501] [ka]

[0502] Compound P-C3 is a copolymer composed of a structural unit derived from compound S19, a structural unit derived from compound S-16, a structural unit derived from compound S-EC6, and a structural unit derived from compound S10 in a molar ratio of 44:5:1:50.

[0503] <Synthesis of Compound P-C4> Compound P-C4 used was synthesized according to the method described in JP-A-2024-110226. JPEG2025129031000155.jpg41157

[0504] Compound P-C4 is a copolymer composed of a structural unit derived from compound S3, a structural unit derived from compound S-EC6, and a structural unit derived from compound S10 in a molar ratio of 49:1:50.

[0505] <Synthesis of compound MC-1> [ka]

[0506] Compound MC-1 was synthesized according to the method described in WO 2009 / 131255.

[0507] <Synthesis of Compound MC-2> Compound MC-2 was synthesized according to the method described in JP-A-2013-147551, and a compound showing an HPLC area percentage value of 99.5% or more was used.

Chemical formula

[0508] <Synthesis of Compound HTL-1> Compound HTL-1 was synthesized according to the method described in JP-A-2012-144722 and used. Compound HTL-1 is a copolymer containing a structural unit derived from Compound S9, a structural unit derived from Compound S10, a structural unit derived from Compound S11, and a structural unit derived from Compound S12 in a molar ratio of 50:30:12.5:7.5.

[0509]

Chemical formula

[0510] Compound S9 synthesized according to the method described in JP-A-2011-174062 was used. Compound S10 synthesized according to the method described in WO 2005 / 049546 was used. A commercially available product was used for Compound S11. Compound S12 synthesized according to the method described in WO 2008 / 106241 was used.

[0511] <Synthesis of HTL-2> HTL-2 synthesized according to the method described in WO 2011 / 093428 was used.

[0512]

Chemical formula

[0513] HTL-2 is a copolymer composed of a structural unit derived from compound S3, a structural unit derived from compound S11, and a structural unit derived from compound S17 in a molar ratio of 50:42.5:7.5.

[0514] HTL-2 is a copolymer composed of a structural unit derived from compound S3, a structural unit derived from compound S11, and a structural unit derived from compound S17 in a molar ratio of 50:42.5:7.5.

[0515] Example D1: Fabrication of light-emitting device D1 (ITO substrate and hole injection layer) An ITO film was formed on 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, Ltd.), was spin-coated to form a film (65 nm thick). The film was then heated on a hot plate at 50°C for 3 minutes in an air atmosphere, and then further heated at 230°C for 15 minutes to form a hole injection layer.

[0516] (Hole transport layer) Compound HTL-1 was dissolved in xylene at a concentration of 0.7% by mass. The resulting xylene solution was spin-coated onto the hole injection layer to form a 20 nm thick film, which was then heated on a hot plate at 200°C for 30 minutes under a nitrogen gas atmosphere. This formed a hole transport layer.

[0517] (Emitting layer) Polymer compound P1 was dissolved in xylene at a concentration of 1.4% by mass. The resulting xylene solution was spin-coated onto the hole transport layer to form a film with a thickness of 80 nm. The film was then heated on a hot plate at 170°C for 10 minutes under a nitrogen gas atmosphere. This formed an emitting layer.

[0518] (Cathode formation) The substrate with the light-emitting layer formed thereon was placed in a vapor deposition apparatus, and the pressure was reduced to 1.0 × 10 Pa or less. Then, sodium fluoride was deposited on the light-emitting layer to a thickness of about 4 nm, and then aluminum was deposited on the sodium fluoride layer to a thickness of about 80 nm to form a cathode. After the deposition, the substrate with the cathode formed thereon was sealed with a glass substrate to produce light-emitting device D1.

[0519] Example D3: Fabrication of light-emitting device D3 Light-emitting element D3 was produced in the same manner as in Example D1, except that "polymer compound P-H1, polymer compound P-E2 (polymer compound P-H1 / polymer compound P-E2 = 80% by mass / 20% by mass)" was used instead of "polymer compound P1" in Example D1.

[0520] <Comparative Example CD1> Fabrication of Light-Emitting Device CD1 (Formation of anode and hole injection layer) An anode was formed by sputtering a 45-nm thick ITO film on a glass substrate. A 65-nm thick film of hole injection material ND-3202 (Nissan Chemical Industries, Ltd.) was then formed on the anode by spin coating. The film was heated on a hot plate at 50°C for 3 minutes in an air atmosphere, and then further heated at 240°C for 15 minutes to form a hole injection layer.

[0521] (Formation of hole transport layer) Polymer compound HTL-1 was dissolved in xylene at a concentration of 0.6% by mass. The resulting xylene solution was spin-coated onto the hole injection layer to form a 20 nm thick film. The film was then heated on a hot plate at 200°C for 30 minutes under a nitrogen gas atmosphere to form a hole transport layer. This heating process crosslinked the polymer compound HTL-1.

[0522] (Formation of light-emitting layer) Compound P-H1 and Compound S-EC1 (Compound P-H1 / Compound S-EC1 = 98.9% by mass / 1.1% by mass) were dissolved in toluene at a concentration of 1.2% by mass. The resulting toluene solution was spin-coated onto the hole transport layer to form a film with a thickness of 85 nm. The film was then heated at 170°C for 10 minutes in a nitrogen gas atmosphere to form an emitting layer.

[0523] (Cathode formation) The substrate with the light-emitting layer formed thereon was placed in a vapor deposition apparatus, and the pressure was reduced to 1.0 × 10 Pa or less. Then, sodium fluoride was deposited on the light-emitting layer to a thickness of about 4 nm, and then aluminum was deposited on the sodium fluoride layer to a thickness of about 80 nm as a cathode. After the deposition, the substrate was sealed with a glass substrate to produce the light-emitting device CD1.

[0524] <Comparative Example CD2> Fabrication of Light-Emitting Device CD2 A light-emitting device CD2 was produced in the same manner as in Example D1, except that the polymer compound P-C1 was used instead of the polymer compound P1 in Example D1.

[0525] <Evaluation of light-emitting elements> EL light emission was observed by applying a voltage to the light-emitting device. 2 Table 3 shows the external quantum efficiency at

[0526] [Table 3]

[0527] Example D4: Fabrication of light-emitting device D4 Light-emitting element D4 was produced in the same manner as in Example D1, except that "polymer compound P-H2, polymer compound P-E1 (polymer compound P-H2 / polymer compound P-E1 = 80% by mass / 20% by mass)" was used instead of "polymer compound P1" in Example D1.

[0528] <Comparative Example CD3> Fabrication of Light-Emitting Device CD3 Light-emitting element CD3 was produced in the same manner as in Example D1, except that "polymer compound P-H2, compound S-EC1 (polymer compound P-H2 / compound S-EC1 = 98.9% by mass / 1.1% by mass)" was used instead of "polymer compound P1" in Example D1.

[0529] <Comparative Example CD4> Fabrication of Light-Emitting Device CD4 A light-emitting device CD4 was produced in the same manner as in Example D1, except that the polymer compound P-C3 was used instead of the polymer compound P1 in Example D1.

[0530] <Comparative Example CD5> Fabrication of light-emitting device A light-emitting device was produced in the same manner as in Example D1, except that "polymer compound P-C4" was used instead of "polymer compound P1" in Example D1.

[0531] <Evaluation of light-emitting elements> EL light emission was observed by applying a voltage to the light-emitting device. 2 Table 4 shows the external quantum efficiency at

[0532] [Table 4]

[0533] Example D5 (ITO substrate and hole injection layer) An ITO film was formed on a glass substrate by sputtering to a thickness of 45 nm to form an anode. A hole injection material, Plexcore® OC AQ-1200, was pin-coated to form a film (thickness: 50 nm) and dried on a hot plate heated to 170°C in air for 15 minutes. This formed a hole injection layer.

[0534] (Hole transport layer) Compound HTL-2 was dissolved in xylene at a concentration of 0.9% by mass. The resulting xylene solution was spin-coated onto the hole injection layer to form a 30 nm thick film, which was then heated on a hot plate at 200°C for 30 minutes under a nitrogen gas atmosphere. This formed a hole transport layer.

[0535] (Emitting layer) Polymer compound P1 was dissolved in xylene at a concentration of 1.4% by mass. The resulting xylene solution was spin-coated onto the hole transport layer to form a film with a thickness of 80 nm. The film was then heated on a hot plate at 170°C for 10 minutes under a nitrogen gas atmosphere. This formed an emitting layer.

[0536] (Cathode formation) The substrate with the light-emitting layer formed thereon was placed in a vapor deposition apparatus, and the pressure was reduced to 1.0 × 10 Pa or less. Then, sodium fluoride was deposited on the light-emitting layer to a thickness of about 4 nm, and then aluminum was deposited on the sodium fluoride layer to a thickness of about 80 nm to form a cathode. After the deposition, the substrate with the cathode formed thereon was sealed with a glass substrate to produce light-emitting device D5.

[0537] <Example D6> Fabrication of light-emitting device D6 Light-emitting device D6 was produced in the same manner as in Example D5, except that "polymer compound P-H2, polymer compound P-E1 (polymer compound P-H2 / polymer compound P-E1 = 80% by mass / 20% by mass)" was used instead of "polymer compound P1" in Example D5.

[0538] <Example D7> Fabrication of light-emitting device D7 Light-emitting device D7 was produced in the same manner as in Example D5, except that "polymer compound P-H2, polymer compound P-E2 (polymer compound P-H2 / polymer compound P-E2 = 80% by mass / 20% by mass)" was used instead of "polymer compound P1" in Example D5.

[0539] <Comparative Example CD6> Fabrication of light-emitting device CD6 Light-emitting element CD6 was produced in the same manner as in Example D5, except that "polymer compound P-H2, compound S-EC1 (polymer compound P-H2 / compound S-EC1 = 98.9% by mass / 1.1% by mass)" was used instead of "polymer compound P1" in Example D5.

[0540] <Comparative Example CD7> Fabrication of light-emitting device CD7 Light-emitting element CD7 was produced in the same manner as in Example D5, except that "polymer compound P-H2, compound S-EC2 polymer compound P-H2 / compound S-EC2 = 98.9% by mass / 1.1% by mass" was used instead of "polymer compound P1" in Example D5.

[0541] <Comparative Example CD8> Fabrication of light-emitting device CD8 Light-emitting element CD8 was produced in the same manner as in Example D5, except that "polymer compound P-H2, compound S-EC3 (polymer compound P-H2 / compound S-EC3 = 98.9% by mass / 1.1% by mass)" was used instead of "polymer compound P1" in Example D5.

[0542] <Evaluation of light-emitting elements> EL light emission was observed by applying a voltage to the light-emitting device. 2 Table 5 shows the external quantum efficiency at

[0543] [Table 5]

[0544] Example D2: Fabrication of light-emitting device A light-emitting device was fabricated in the same manner as in Example D1, except that "polymer compound P1, complex MC-1 (polymer compound P1 / complex MC-1 = 58% by mass / 42% by mass)" was used instead of "polymer compound P1" in Example D1.

[0545] Example D8: Fabrication of light-emitting device D8 Light-emitting device D8 was produced in the same manner as in Example D1, except that "polymer compound P-H1, polymer compound S-E2, complex MC-1 (polymer compound P-H1 / polymer compound P-E2 / complex MC-1=48% by mass / 10% by mass / 42% by mass)" was used instead of "polymer compound P1" in Example D1.

[0546] <Comparative Example CD9> Fabrication of Light-Emitting Device CD9 Light-emitting element CD9 was produced in the same manner as in Example D1, except that "polymer compound P-H1, compound S-EC1, complex MC-1 (polymer compound P-H1 / compound S-EC1 / complex MC-1 = 56.9% by mass / 1.1% by mass / 42% by mass)" was used instead of "polymer compound P1" in Example D1.

[0547] <Comparative Example CD10> Fabrication of Light-Emitting Device CD10 The light-emitting element CD10 was produced in the same manner as in Example D1, except that the polymer compound P1 in Example D1 was replaced with polymer compound P-C1, complex MC-1 (polymer compound P-C1 / complex MC-1 = 58% by mass / 42% by mass).

[0548] <Comparative Example CD11> Fabrication of Light-Emitting Device CD11 Light-emitting element CD11 was produced in the same manner as in Example D1, except that "polymer compound P-C2, complex MC-2 (polymer compound P-C2 / complex MC-2 = 85% by mass / 15% by mass)" was used instead of "polymer compound P1" in Example D1.

[0549] <Evaluation of light-emitting elements> EL light emission was observed by applying a voltage to the light-emitting device. 2 Table 6 shows the external quantum efficiency at

[0550] [Table 6]

[0551] Example D9: Fabrication of light-emitting element D9 Light-emitting device D9 was produced in the same manner as in Example D1, except that "polymer compound P3, complex MC-1 (polymer compound P3 / complex MC-1 = 58% by mass / 42% by mass)" was used instead of "polymer compound P1" in Example D1.

[0552] Example D10: Fabrication of light-emitting device D10 Light-emitting device D10 was produced in the same manner as in Example D1, except that "polymer compound P-H1, polymer compound P-E1, complex MC-1 (polymer compound P-H1 / polymer compound P-E1 / complex MC-1 = 48 mass% / 10 mass% / 42 mass%)" was used instead of "polymer compound P1" in Example D1.

[0553] <Comparative Example CD12> Fabrication of Light-Emitting Device CD12 Light-emitting element CD12 was produced in the same manner as in Example D1, except that "polymer compound P-H1, compound S-EC3, complex MC-1 (polymer compound P-H1 / compound S-EC3 / complex MC-1 = 56.9% by mass / 1.1% by mass / 42% by mass)" was used instead of "polymer compound P1" in Example D1.

[0554] <Comparative Example CD13> Fabrication of Light-Emitting Device CD13 Light-emitting element CD13 was produced in the same manner as in Example D1, except that "polymer compound P-H1, compound S-EC2, complex MC-1 (polymer compound P-H1 / compound S-EC2 / complex MC-1 = 56.9% by mass / 1.1% by mass / 42% by mass)" was used instead of "polymer compound P1" in Example D1.

[0555] <Evaluation of light-emitting elements> EL light emission was observed by applying a voltage to the light-emitting device. 2 Table 7 shows the external quantum efficiency at

[0556] [Table 7]

[0557] Example D11: Fabrication of light-emitting device D11 Light-emitting device D11 was produced in the same manner as in Example D1, except that "polymer compound P-H2, polymer compound P-E1 (polymer compound P-H2 / polymer compound P-E1 = 80% by mass / 20% by mass)" was used instead of "polymer compound P1" in Example D1.

[0558] <Comparative Example CD14> Fabrication of Light-Emitting Device CD14 Light-emitting element CD14 was produced in the same manner as in Example D1, except that "polymer compound P-H2, polymer compound P-EC1 (polymer compound P-H2 / polymer compound P-EC1 = 80% by mass / 20% by mass)" was used instead of "polymer compound P1" in Example D1.

[0559] <Evaluation of light-emitting elements> EL light emission was observed by applying a voltage to the light-emitting device. 2 Table 8 shows the external quantum efficiency at

[0560] [Table 8]

[0561] Example D12: Fabrication of light-emitting device D12 Light-emitting element D12 was produced in the same manner as in Example D1, except that "polymer compound P-H2, polymer compound P-E1, complex MC-1 (polymer compound P-H2 / polymer compound P-E1 / complex MC-1 = 48% by mass / 10% by mass / 42% by mass)" was used instead of "polymer compound P1" in Example D1.

[0562] <Comparative Example CD15> Fabrication of Light-Emitting Device CD15 Light-emitting element CD15 was produced in the same manner as in Example D1, except that "polymer compound P-H2, polymer compound P-EC1, complex MC-1 (polymer compound P-H2 / polymer compound P-EC1 / complex MC-1 = 48% by mass / 10% by mass / 42% by mass)" was used instead of "polymer compound P1" in Example D1.

[0563] <Evaluation of light-emitting elements> EL light emission was observed by applying a voltage to the light-emitting device. 2 Table 9 shows the external quantum efficiency at

[0564] [Table 9]

[0565] As shown in Tables 3 to 9, it was found that the light-emitting devices containing the polymer compounds according to the present disclosure have excellent external quantum efficiency.

Claims

1. A polymer compound comprising a structural unit having a group in which one or more hydrogen atoms have been removed from a fused ring compound represented by formula (1), and at least one structural unit selected from a structural unit represented by formula (X) and a structural unit represented by formula (Y). 【Chemical 1】 [In formula (1), X １ are >O, >N-R', >C(-R'') ２ , >S or >Se. R' represents an optionally substituted aryl group, an optionally substituted monovalent heterocyclic group, an optionally substituted alkyl group, or an optionally substituted cycloalkyl group. R'' represents a hydrogen atom, an aryl group which may have a substituent, an alkyl group which may have a substituent, or a cycloalkyl group which may have a substituent. The >N-R' and / or the >C(-R'') ２ R' and R'' are X containing the R' and R'' １ may be bonded to Z adjacent to any carbon atom to which is directly bonded via a linking group or a single bond. Z is -C(-R Ｚ )= or -N=, and two adjacent Zs are -C(-R Ｚ ) ２ -, -Si(-R Ｚ ) ２ -, -N(-R Ｚ ) -, -O-, -S- or -Se-, R Ｚ is a hydrogen atom or a substituent, and R Ｚ Adjacent groups among these are bonded to each other to form the R Ｚ may form a ring together with the ring to which it is attached, and the ring formed may be substituted. Multiple occurrences of the symbol may be the same or different. 【Chemistry 2】 [In formula (X), 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. When a plurality of such substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded. Ar Ｘ２ and Ar Ｘ４ each independently represents an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, and these groups may have a substituent. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded. Ｘ２ When a plurality of Ar are present, they may be the same or different. Ｘ４ When there are a plurality of groups, 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. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded. Ｘ２ When a plurality of R are present, they may be the same or different. Ｘ３ When there are multiple, they may be the same or different. 【Chemistry 3】 [In formula (Y), 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. When a plurality of such substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded.]

2. X in the formula (1) １ The polymer compound according to claim 1, wherein is >N-R'.

3. 3. The polymer compound according to claim 2, wherein the fused ring compound represented by formula (1) is a compound represented by formula (1-1). 【Chemistry 4】 [In formula (1-1), R Ｚ and R′ have the same meaning as above.]

4. Ar in formula (Y) Ｙ１ is a phenylene group which may have a substituent, a fluorenediyl group which may have a substituent, or a group represented by formula (YY): 【Chemistry 5】 [In formula (YY), Ar ＹＹ１ and Ar ＹＹ３ each independently represents an arylene group which may have a substituent, Ar ＹＹ２ represents a divalent nitrogen-containing aromatic heterocyclic group which may have a substituent.]

5. A composition comprising the polymer compound according to claim 1 and a metal complex represented by formula (Z): 【Chemistry 6】 [In formula (Z), M １ represents a ruthenium atom, 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. １ When is a ruthenium atom, a rhodium atom, or an iridium atom, n １ +n ２ is 3, and M １ When is a palladium atom or a platinum atom, n １ +n ２ is 2. E １ and E ２ each independently represents a nitrogen atom or a carbon atom. １ and E ２ When there are a plurality of groups, they may be the same or different. Ring L １ represents an aromatic heterocycle, and the ring 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 there are multiple groups, 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 the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded. Ring L ２ When there are multiple groups, they may be the same or different. Ring L １ and a substituent that may be present on ring L ２ The substituents which may be possessed by the group may be bonded to each other to form a ring together with the atoms 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 there are multiple groups, they may be the same or different.

6. A composition comprising 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, and the polymer compound according to any one of claims 1 to 4.

7. A light-emitting device comprising an anode, a cathode, and an organic layer provided between the anode and the cathode, the organic layer comprising the polymer compound according to any one of claims 1 to 4.

8. The method includes a step of polymerizing a compound having a polymerizable group in the presence of a transition metal catalyst and an inorganic base, The compound having the polymerizable group has two or more boron atoms, a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, and sp ３ and at least one selected from the group consisting of carbon atoms, and a fused ring compound having a polymerizable group, wherein the fused heterocyclic ring skeleton satisfies at least one of requirements (i) and (ii). (i) The nitrogen atom, the oxygen atom, the sulfur atom, the selenium atom, and the sp ３ The total number of carbon atoms is 4 or more. (ii) The number of nitrogen atoms contained in the ring of the fused heterocyclic skeleton is 2 or more.

9. The method for producing a polymer compound according to claim 8, wherein the fused ring compound is a fused ring compound represented by formula (BM-1): 【Chemistry 7】 [In formula (BM-1), Ring R ｂ１ , ring R ｂ２ , ring R ｂ３ , ring R ｂ４ and ring R ｂ５ each independently represents an aromatic hydrocarbon ring or a heterocyclic ring, and these rings may have a substituent. When a plurality of such substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded. X ｂ１ , X ｂ２ , X ｂ３ and X ｂ４ each independently represents an oxygen atom, a sulfur atom, a selenium atom, or —N(R ｘｂ )-, an alkylene group, or a cycloalkylene group, and these groups may have a substituent. When a plurality of such substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded. Ring R ｂ１ , ring R ｂ２ , ring R ｂ３ , ring R ｂ４ , ring R ｂ５ , X ｂ１ , X ｂ２ , X ｂ３ and X ｂ４ At least one of the groups has a polymerizable group. R ｘｂ 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. When a plurality of such substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded. X ｂ１ and ring R ｂ１ , X ｂ１ and ring R ｂ２ , X ｂ２ and ring R ｂ１ , X ｂ２ and ring R ｂ３ , X ｂ３ and ring R ｂ２ , X ｂ３ and ring R ｂ４ , X ｂ４ and ring R ｂ４ , X ｂ４ and ring R ｂ５ , ring R ｂ２ and ring R ｂ３ , ring R ｂ２ and ring R ｂ５ , and ring R ｂ３ and ring R ｂ５ may each independently bond directly or via a divalent or higher valent group which may have a substituent to form a ring. When a plurality of such substituents are present, they may be the same or different and may bond to each other to form a ring together with the atom to which they are bonded.

10. The method for producing a polymer compound according to claim 9, wherein the fused ring compound represented by formula (BM-1) is a fused ring compound represented by formula (BM-2). 【Chemistry 8】 [In formula (BM-2), Ring R ｂ１ , ring R ｂ２ , ring R ｂ３ , ring R ｂ４ , ring R ｂ５ , X ｂ２ and X ｂ４ represents the same meaning as above. Ring R Ｘｂ１ and ring R Ｘｂ２ each independently represents an aromatic hydrocarbon ring or a heterocyclic ring, and these rings may have a substituent. When a plurality of such substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded. Ring R ｂ１ , ring R ｂ２ , ring R ｂ３ , ring R ｂ４ , ring R ｂ５ , ring R Ｘｂ１ , ring R Ｘｂ２ , X ｂ１ , X ｂ２ , X ｂ３ and X ｂ４ At least one of the groups has a polymerizable group. Ring R Ｘｂ１ and ring R ｂ１ , ring R Ｘｂ１ and ring R Ｘｂ２ , and ring R Ｘｂ２ and ring R ｂ４ may each independently bond directly or via a divalent or higher valent group which may have a substituent to form a ring. When a plurality of such substituents are present, they may be the same or different and may bond to each other to form a ring together with the atom to which they are bonded.

11. The method for producing a polymer compound according to claim 10, wherein the fused ring compound represented by formula (BM-2) is a fused ring compound represented by formula (1M). 【Chemistry 9】 [In formula (1M), X １ are >O, >N-R', >C(-R'') ２ , >S or >Se. R' represents an optionally substituted aryl group, an optionally substituted monovalent heterocyclic group, an optionally substituted alkyl group, or an optionally substituted cycloalkyl group. R'' represents a hydrogen atom, an aryl group which may have a substituent, an alkyl group which may have a substituent, or a cycloalkyl group which may have a substituent. The >N-R' and / or the >C(-R'') ２ R' and R'' are X containing the R' and R'' １ may be bonded to Z adjacent to any carbon atom to which is directly bonded via a linking group or a single bond. Z is -C(-R Ｚ )= or -N=, and two adjacent Zs are -C(-R Ｚ ) ２ -, -Si(-R Ｚ ) ２ -, -N(-R Ｚ ) -, -O-, -S- or -Se-, R Ｚ is a hydrogen atom or a substituent, and R Ｚ Adjacent groups among these are bonded to each other to form the R Ｚ may form a ring together with the ring to which it is attached, and the ring formed may be substituted. Multiple Zs and Xs １ At least one of the groups has a polymerizable group. Multiple occurrences of the symbol may be the same or different.

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