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Definitions

• the present invention relates to a polymer compound, a composition containing the polymer compound, a liquid composition, a thin film and an element, and a planar light source and a display device including the element.
• a light-emitting element including a composition obtained by doping a host material with a light-emitting organometallic complex as a dopant as a material for a light-emitting layer exhibits high-efficiency light-emitting characteristics (Patent Document 1).
• Patent Document 1 specifically describes a material that provides a long-life element when used in the production of a light-emitting element such as an organic electroluminescence element (hereinafter referred to as “organic EL element”). It wasn't.
• an object of the present invention is to provide a material that provides an element having a long lifetime when used for manufacturing a light emitting element such as an organic EL element.
• R 1 , R 2 , R 3 , R 4 and R 5 are each independently a hydrogen atom, alkyl group, alkoxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkoxy group, Arylalkylthio group, acyl group, acyloxy group, amide group, acid imide group, imine residue, substituted silyl group, substituted silyloxy group, substituted silylthio group, monovalent aromatic heterocyclic group, heteroaryloxy group, heteroarylthio Represents a group, an arylalkenyl group, an arylalkynyl group, a substituted carboxyl group, or a cyano group, and at least one of R 1 , R 2 ,
• Ar 1 and Ar 2 are each independently an alkyl group, alkoxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkoxy group, arylalkylthio group, acyl group, acyloxy group, amide group , Acid imide group, imine residue, substituted silyl group, substituted silyloxy group, substituted silylthio group, monovalent aromatic heterocyclic group, heteroaryloxy group, heteroarylthio group, arylalkenyl group, arylalkynyl group, substituted carboxyl And a divalent aromatic group which may have a substituent selected from the group consisting of a group and a cyano group.
• Ar 3 represents an aryl group or a monovalent aromatic heterocyclic group.
• Ar 4 is a hydrogen atom, alkyl group, alkoxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkoxy group, arylalkylthio group, acyl group, acyloxy group, amide group, acid imide group , Imine residue, substituted amino group, substituted silyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group, monovalent aromatic heterocyclic group, heteroaryloxy group, heteroarylthio group, arylalkenyl group, arylalkynyl Represents a group, a substituted carboxyl group, or a cyano group.
• R 6 is an alkyl group, alkoxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkoxy group, arylalkylthio group, acyl group, acyloxy group, amide group, acid imide group, imine residue Group, substituted amino group, substituted silyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group, monovalent aromatic heterocyclic group, heteroaryloxy group, heteroarylthio group, arylalkenyl group, arylalkynyl group, substituted Represents a carboxyl group or a cyano group.
• R 6 When a plurality of R 6 are present, they may be the same or different. a represents 0 or 1; Two a's may be the same or different. ) [2] At least one of R 1 , R 2 , R 3 , R 4 and R 5 is a group containing an alkyl group, and the alkyl group in the group containing the alkyl group has 6 aliphatic carbon atoms.
• [3] The polymer compound according to [1] or [2], wherein at least one of R 1 , R 2 , R 3 , R 4 and R 5 is an alkyl group having 12 or more carbon atoms.
• R ′ represents a hydrogen atom or an alkyl group.
• the total ratio of the repeating unit represented by the formula (1) and the repeating unit represented by the formula (2) to all repeating units constituting the polymer compound is 30 mol% or more.
• Ar 5 represents an arylene group or a divalent aromatic heterocyclic group.
• Ar 6 and Ar 7 are each independently an alkyl group, alkoxy group, alkylthio group, aryloxy group, arylthio group, arylalkyl group, arylalkoxy group, arylalkylthio group, acyl group, acyloxy group, amide group, acid imide Group, imine residue, substituted amino group, substituted silyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group, heteroaryloxy group, heteroarylthio group, arylalkenyl group, arylalkynyl group, substituted carboxyl group, or cyano Represents a group.
• R 7 is an alkyl group, alkoxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkoxy group, arylalkylthio group, acyl group, acyloxy group, amide group, acid imide group, imine residue Group, substituted amino group, substituted silyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group, monovalent aromatic heterocyclic group, heteroaryloxy group, heteroarylthio group, arylalkenyl group, arylalkynyl group, substituted Represents a carboxyl group or a cyano group.
• the repeating unit represented by the formula (5) is selected from the group consisting of a repeating unit represented by the formula (7) and a repeating unit represented by the formula (8). High molecular compound.
• R 8 and R 9 are each independently an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, an acyl group, an acyloxy group
• R 10 and R 11 are each independently an alkyl group, alkoxy group, alkylthio group, aryl group, aryloxy group, arylthio group,
• Ar 8 , Ar 9 , Ar 10 and Ar 14 each independently represent an arylene group or a divalent aromatic heterocyclic group.
• Ar 11 , Ar 12 and Ar 13 each independently represent aryl.
• a composition comprising the polymer compound according to any one of [1] to [12] and at least one material selected from the group consisting of a hole transport material, an electron transport material and a light emitting material. .
• a liquid composition comprising the polymer compound according to any one of [1] to [12] and a solvent or a dispersion medium.
• [17] A device having an electrode composed of an anode and a cathode, and an organic layer containing the polymer compound according to any one of [1] to [12] provided between the electrodes.
• a planar light source comprising the element according to [17].
• a display device comprising the element according to [17].
• a compound represented by formula (i). (In the formula, R a , R f and R g each independently represent a hydrogen atom or an alkyl group, and R b , R c , R d and R e are each independently an alkyl group or an alkyl group.
• Ar 1 and Ar 2 each independently represents an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, Acyl group, acyloxy group, amide group, acid imide group, imine residue, substituted silyl group, substituted silyloxy group, substituted silylthio group, monovalent aromatic heterocyclic group, heteroaryloxy group, heteroarylthio group, arylalkenyl Having a substituent selected from the group consisting of a group, an arylalkynyl group, a substituted carboxyl group, and a cyano group.
• X represents a halogen atom, a boric acid ester residue, a boric acid residue, a group represented by the formula (a-1), or a formula (a-2).
• a group, a group represented by the formula (a-3), or a group represented by the formula (a-4), and two Xs may be the same or different.
• RT represents an alkyl group or an aryl group.
• X A represents a halogen atom.
• X A has the same meaning as described above.
• R T is, R T present .3 pieces of the same meaning as described above may be the same or different.
• the polymer compound and composition of the present invention (hereinafter also referred to as “the polymer compound of the present invention”) provide a long-life device when used in the production of an organic EL device or the like.
• the polymer compound or the like of the present invention provides a device that is further excellent in luminous efficiency (that is, high quantum yield). Therefore, the polymer compound of the present invention is particularly useful for the production of light emitting devices such as organic EL devices.
• halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
• “Repeating unit” means a unit present in two or more in a polymer compound.
• C m -C n (m and n are positive integers satisfying m ⁇ n) indicates that the organic group described immediately after the term has m to n carbon atoms. .
• unsubstituted appended immediately before a group means that the hydrogen atom of the group is not substituted with a substituent.
• substituted immediately before a group means that part or all of the hydrogen atoms of the group are substituted with a substituent.
• which may have a substituent” attached immediately before a group means that when a hydrogen atom of the group is not substituted with a substituent, and a part or all of the hydrogen atoms of the group Means when both are substituted with a substituent.
• examples of the substituent include a halogen atom, a hydrocarbyl group having 1 to 30 carbon atoms, and a hydrocarbyloxy group having 1 to 30 carbon atoms.
• substituent include a halogen atom, a hydrocarbyl group having 1 to 30 carbon atoms, and a hydrocarbyloxy group having 1 to 30 carbon atoms.
• halogen atoms, 1 to 30 carbon atoms are exemplified.
• 18 hydrocarbyl groups and hydrocarbyloxy groups having 1 to 18 carbon atoms are preferred, halogen atoms, hydrocarbyl groups having 1 to 12 carbon atoms and hydrocarbyloxy groups having 1 to 12 carbon atoms are more preferred, and halogen atoms and carbon atoms.
• a hydrocarbyl group having 1 to 12 carbon atoms is more preferable, and a hydrocarbyl group having 1 to 6 carbon atoms is particularly preferable.
• the alkyl group means an unsubstituted alkyl group and an alkyl group substituted with a substituent such as a halogen atom, an amino group, or a mercapto group.
• the alkyl group includes both a linear alkyl group and a cyclic alkyl group (cycloalkyl group).
• the alkyl group may have a branch.
• the number of carbon atoms of the alkyl group is usually 1 to 20, not including the number of carbon atoms of the substituent.
• alkyl group examples include a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, hexyl group, cyclohexyl group, heptyl group, octyl group, 2-ethylhexyl group, Nonyl group, decyl group, 4-methyldodecyl group, pentadecyl group, 2,2,4,4,6,8,8-heptamethylnonyl group, heptadecyl group, octadecyl group, 2,6,10,14-tetramethyl Pentadecyl group, nonadecyl group, 3,7-dimethyloctyl group, dodecyl group, trifluoromethyl group, pentafluoroethyl group, perfluorobutyl group, perfluorohexyl group,
• Examples of the C 1 -C 20 alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isoamyl group, a hexyl group, and a cyclohexyl group.
• the alkoxy group means an unsubstituted alkoxy group and an alkoxy group substituted with a substituent such as a halogen atom and an alkoxy group.
• the alkoxy group includes both a linear alkoxy group and a cyclic alkoxy group (cycloalkoxy group).
• the alkoxy group may have a branch.
• the number of carbon atoms of the alkoxy group does not include the number of carbon atoms of the substituent, and is usually 1 to 20, preferably 1 to 15, and more preferably 1 to 10.
• alkoxy group examples include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, a tert-butoxy group, a pentyloxy group, a hexyloxy group, a cyclohexyloxy group, a heptyloxy group, and an octyloxy group.
• Examples of the C 1 -C 12 alkoxy group include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, a tert-butoxy group, a pentyloxy group, a hexyloxy group, a cyclohexyloxy group, and a heptyl group.
• Examples thereof include an oxy group, an octyloxy group, a 2-ethylhexyloxy group, a nonyloxy group, a decyloxy group, a 3,7-dimethyloctyloxy group, and a dodecyloxy group.
• the alkylthio group means an unsubstituted alkylthio group and an alkylthio group substituted with a substituent such as a halogen atom.
• the alkylthio group includes both a linear alkylthio group and a cyclic alkylthio group (cycloalkylthio group).
• the alkylthio group may have a branch.
• the number of carbon atoms of the alkylthio group is usually 1 to 20, preferably 1 to 15, more preferably 1 to 10, not including the number of carbon atoms of the substituent.
• alkylthio group examples include methylthio group, ethylthio group, propylthio group, isopropylthio group, butylthio group, isobutylthio group, tert-butylthio group, pentylthio group, hexylthio group, cyclohexylthio group, heptylthio group, octylthio group, 2- Examples thereof include an ethylhexylthio group, a nonylthio group, a decylthio group, a 3,7-dimethyloctylthio group, a dodecylthio group, and a trifluoromethylthio group.
• Examples of the C 1 -C 12 alkylthio group include a methylthio group, an ethylthio group, a propylthio group, an isopropylthio group, a butylthio group, an isobutylthio group, a tert-butylthio group, a pentylthio group, a hexylthio group, a cyclohexylthio group, a heptylthio group, Examples include octylthio group, 2-ethylhexylthio group, nonylthio group, decylthio group, 3,7-dimethyloctylthio group, and dodecylthio group.
• the aryl group is a remaining atomic group obtained by removing one hydrogen atom bonded to a carbon atom constituting an aromatic ring from an aromatic hydrocarbon.
• the aryl group means an unsubstituted aryl group and an aryl group substituted with a substituent such as a halogen atom, an alkoxy group and an alkyl group.
• An aryl group has a condensed ring; a single bond of two or more rings selected from an independent benzene ring and a condensed ring; and two or more rings selected from an independent benzene ring and a condensed ring are divalent And those bonded via an organic group (for example, alkenylene group such as vinylene group) are also included.
• the number of carbon atoms of the aryl group is usually 6 to 60, preferably 7 to 48, more preferably 7 to 30, excluding the number of carbon atoms of the substituent.
• the aryl group include a phenyl group, a C 1 to C 12 alkoxyphenyl group, a C 1 to C 12 alkylphenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthracenyl group, a 2-anthracenyl group, and 9- Examples include an anthracenyl group and a pentafluorophenyl group, and a C 1 to C 12 alkoxyphenyl group or a C 1 to C 12 alkylphenyl group is preferable.
• Examples of the C 1 to C 12 alkoxyphenyl group include a methoxyphenyl group, an ethoxyphenyl group, a propyloxyphenyl group, an isopropyloxyphenyl group, a butoxyphenyl group, an isobutoxyphenyl group, a tert-butoxyphenyl group, and a pentyloxyphenyl group.
• Examples of the C 1 -C 12 alkylphenyl group include methylphenyl group, ethylphenyl group, dimethylphenyl group, propylphenyl group, mesityl group, methylethylphenyl group, isopropylphenyl group, butylphenyl group, isobutylphenyl group, tert -Butylphenyl group, pentylphenyl group, isoamylphenyl group, hexylphenyl group, heptylphenyl group, octylphenyl group, nonylphenyl group, decylphenyl group and dodecylphenyl group.
• the aryloxy group means an unsubstituted aryloxy group and an aryloxy group substituted with a substituent such as a halogen atom, an alkoxy group and an alkyl group.
• the number of carbon atoms of the aryloxy group is usually 6 to 60, preferably 7 to 48, more preferably 7 to 30, excluding the number of carbon atoms of the substituent.
• Examples of the aryloxy group include a phenoxy group, a C 1 -C 12 alkoxyphenoxy group, a C 1 -C 12 alkylphenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, and a pentafluorophenyloxy group.
• a C 1 -C 12 alkoxyphenoxy group or a C 1 -C 12 alkylphenoxy group is preferred.
• Examples of the C 1 -C 12 alkoxyphenoxy group include methoxyphenoxy group, ethoxyphenoxy group, propyloxyphenoxy group, isopropyloxyphenoxy group, butoxyphenoxy group, isobutoxyphenoxy group, tert-butoxyphenoxy group, pentyloxyphenoxy group Hexyloxyphenoxy group, cyclohexyloxyphenoxy group, heptyloxyphenoxy group, octyloxyphenoxy group, 2-ethylhexyloxyphenoxy group, nonyloxyphenoxy group, decyloxyphenoxy group, 3,7-dimethyloctyloxyphenoxy group and dodecyloxy A phenoxy group is mentioned.
• Examples of the C 1 -C 12 alkylphenoxy group include a methylphenoxy group, an ethylphenoxy group, a dimethylphenoxy group, a propylphenoxy group, a 1,3,5-trimethylphenoxy group, a methylethylphenoxy group, an isopropylphenoxy group, and a butylphenoxy group.
• the arylthio group means an unsubstituted arylthio group and an arylthio group substituted with a substituent such as a halogen atom, an alkoxy group and an alkyl group.
• the number of carbon atoms of the arylthio group is usually 6 to 60, preferably 7 to 48, more preferably 7 to 30, excluding the number of carbon atoms of the substituent.
• arylthio group examples include a phenylthio group, a C 1 -C 12 alkoxyphenylthio group, a C 1 -C 12 alkylphenylthio group, a 1-naphthylthio group, a 2-naphthylthio group, and a pentafluorophenylthio group.
• the arylalkyl group means an unsubstituted arylalkyl group and an arylalkyl group substituted with a substituent such as a halogen atom, an alkoxy group and an alkyl group.
• the number of carbon atoms of the arylalkyl group is usually 7 to 60, preferably 7 to 48, more preferably 7 to 30, excluding the number of carbon atoms of the substituent.
• arylalkyl group examples include a phenyl-C 1 -C 20 alkyl group, a C 1 -C 12 alkoxyphenyl-C 1 -C 12 alkyl group, a C 1 -C 12 alkylphenyl-C 1 -C 20 alkyl group, naphthyl -C 1 ⁇ C 20 alkyl group and 2-naphthyl -C 1 ⁇ C 20 alkyl group.
• the arylalkoxy group means an unsubstituted arylalkoxy group and an arylalkoxy group substituted with a substituent such as a halogen atom, an alkoxy group and an alkyl group.
• the number of carbon atoms of the arylalkoxy group is usually 7 to 60, preferably 7 to 48, more preferably 7 to 30, excluding the number of carbon atoms of the substituent.
• arylalkoxy group examples include a phenyl-C 1 -C 12 alkoxy group, a C 1 -C 12 alkoxyphenyl-C 1 -C 12 alkoxy group, a C 1 -C 12 alkylphenyl-C 1 -C 12 alkoxy group, naphthyl -C 1 ⁇ C 12 alkoxy group and 2-naphthyl -C 1 ⁇ C 12 alkoxy group.
• the arylalkylthio group means an unsubstituted arylalkylthio group and an arylalkylthio group substituted with a substituent such as a halogen atom, an alkoxy group and an alkyl group.
• the number of carbon atoms of the arylalkylthio group is usually 7 to 60, preferably 7 to 48, more preferably 7 to 30, excluding the number of carbon atoms of the substituent.
• arylalkylthio group examples include a phenyl-C 1 to C 12 alkylthio group, a C 1 to C 12 alkoxyphenyl-C 1 to C 12 alkylthio group, a C 1 to C 12 alkylphenyl-C 1 to C 12 alkylthio group, naphthyl -C 1 ⁇ C 12 alkylthio group and a 2-naphthyl -C 1 ⁇ C 12 alkylthio group.
• the arylalkenyl group means an unsubstituted arylalkenyl group and an arylalkenyl group substituted with a substituent such as a halogen atom, an alkoxy group and an alkyl group.
• the number of carbon atoms of the arylalkenyl group is usually 8 to 60, preferably 8 to 48, more preferably 8 to 30, excluding the number of carbon atoms of the substituent.
• Examples of the arylalkenyl group include a phenyl-C 2 -C 12 alkenyl group, a C 1 -C 12 alkoxyphenyl-C 2 -C 12 alkenyl group, a C 1 -C 12 alkylphenyl-C 2 -C 12 alkenyl group, Examples include 1-naphthyl-C 2 -C 12 alkenyl group and 2-naphthyl-C 2 -C 12 alkenyl group, C 1 -C 12 alkoxyphenyl-C 2 -C 12 alkenyl group or C 1 -C 12 alkylphenyl -C 2 -C 12 alkenyl groups are preferred.
• Examples of the C 2 -C 12 alkenyl group include a vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 1-pentenyl group, 2-pentenyl group, 1-hexenyl group, Examples include 2-hexenyl group and 1-octenyl group.
• the arylalkynyl group means an unsubstituted arylalkynyl group and an arylalkynyl group substituted with a substituent such as a halogen atom, an alkoxy group, and an alkyl group.
• the number of carbon atoms of the arylalkynyl group is usually 8 to 60, preferably 8 to 48, more preferably 8 to 30, excluding the number of carbon atoms of the substituent.
• the arylalkynyl group includes phenyl-C 2 -C 12 alkynyl group, C 1 -C 12 alkoxyphenyl-C 2 -C 12 alkynyl group, C 1 -C 12 alkylphenyl-C 2 -C 12 alkynyl group, 1- And naphthyl-C 2 -C 12 alkynyl group and 2-naphthyl-C 2 -C 12 alkynyl group, C 1 -C 12 alkoxyphenyl-C 2 -C 12 alkynyl group or C 1 -C 12 alkylphenyl-C A 2 to C 12 alkynyl group is preferred.
• Examples of the C 2 -C 12 alkynyl group include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 1-pentynyl group, 2-pentynyl group, 1-hexynyl group, Examples include 2-hexynyl group and 1-octynyl group.
• the heteroaryloxy group means an unsubstituted heteroaryloxy group and a substituted heteroaryloxy group.
• the number of carbon atoms of the heteroaryloxy group is usually 6 to 60, preferably 7 to 48, not including the number of carbon atoms of the substituent.
• Examples of heteroaryloxy groups include C 1 -C 12 alkoxypyridyloxy groups, C 1 -C 12 alkylpyridyloxy groups, thienyloxy groups, C 1 -C 12 alkoxythienyloxy groups, pyridyloxy groups, and isoquinolyl groups.
• An oxy group, and a C 1 -C 12 alkoxypyridyloxy group or a C 1 -C 12 alkylpyridyloxy group is preferred.
• Examples of the C 1 -C 12 alkoxypyridyloxy group include methoxypyridyloxy group, ethoxypyridyloxy group, propyloxypyridyloxy group, isopropyloxypyridyloxy group, butoxypyridyloxy group, isobutoxypyridyloxy group, sec-butoxy Pyridyloxy group, tert-butoxypyridyloxy group, pentyloxypyridyloxy group, hexyloxypyridyloxy group, cyclohexyloxypyridyloxy group, heptyloxypyridyloxy group, octyloxypyridyloxy group, 2-ethylhexyloxypyridyloxy group, nonyl Examples thereof include an oxypyridyloxy group, a decyloxypyridyloxy group, a 3,7-dimethyloctyloxypyri
• Examples of the C 1 -C 12 alkylpyridyloxy group include a methylpyridyloxy group, an ethylpyridyloxy group, a dimethylpyridyloxy group, a propylpyridyloxy group, a 1,3,5-trimethylpyridyloxy group, and a methylethylpyridyloxy group.
• the heteroarylthio group means an unsubstituted heteroarylthio group and a substituted heteroarylthio group.
• the number of carbon atoms of the heteroarylthio group is usually 6 to 60, preferably 7 to 48, not including the number of carbon atoms of the substituent.
• Examples of the heteroarylthio group include a pyridylthio group, a C 1 -C 12 alkoxypyridylthio group, a C 1 -C 12 alkylpyridylthio group, and an isoquinolylthio group, and a C 1 -C 12 alkoxypyridylthio group or C 1 ⁇ C 12 alkylpyridylthio groups are preferred.
• the monovalent aromatic heterocyclic group means a remaining atomic group obtained by removing one hydrogen atom directly bonded to an aromatic ring from an aromatic heterocyclic compound, and includes those having a condensed ring. .
• the monovalent aromatic heterocyclic group means an unsubstituted monovalent aromatic heterocyclic group and a monovalent aromatic heterocyclic group substituted with a substituent such as an alkyl group.
• Heterocyclic compounds are not only carbon atoms but also hetero atoms such as oxygen atoms, sulfur atoms, nitrogen atoms, phosphorus atoms, boron atoms and silicon atoms as elements constituting the ring among organic compounds having a cyclic structure. The thing containing an atom.
• heterocyclic compound having aromaticity examples include heterocyclic compounds containing heteroatoms such as oxadiazole, thiadiazole, thiazole, oxazole, thiophene, pyrrole, phospho-isoquinoline, carbazole and dibenzophosphole.
• Heterocycle itself is aromatic; heterocyclic compounds containing heteroatoms, such as phenoxazine, phenothiazine, dibenzoborol, dibenzosilol and dibenzopyran, including heteroatoms contained in the compound Heterocycles themselves do not exhibit aromaticity, but those having a structure in which an aromatic ring is condensed to a heterocyclic ring can be mentioned.
• the number of carbon atoms of the monovalent aromatic heterocyclic group is usually 4 to 60, preferably 4 to 30, excluding the number of carbon atoms of the substituent.
• Examples of the monovalent aromatic heterocyclic group include thienyl group, C 1 to C 12 alkyl thienyl group, pyrrolyl group, furyl group, pyridyl group, C 1 to C 12 alkyl pyridyl group, pyridazinyl group, pyrimidyl group, and pyrazinyl.
• the amino group is an unsubstituted amino group and an amino group substituted with one or two substituents selected from an alkyl group, an aryl group, an arylalkyl group, and a monovalent aromatic heterocyclic group (hereinafter referred to as “amino group”). , "Substituted amino group”).
• the substituent may further have a substituent (hereinafter sometimes referred to as “secondary substituent”).
• the number of carbon atoms of the substituted amino group is usually 1 to 60, preferably 2 to 48, more preferably 2 to 40, not including the number of carbon atoms of the secondary substituent.
• substituted amino group examples include methylamino group, dimethylamino group, ethylamino group, diethylamino group, propylamino group, dipropylamino group, isopropylamino group, di-isopropylamino group, butylamino group, isobutylamino group, sec-butylamino group, tert-butylamino group, pentylamino group, hexylamino group, heptylamino group, octylamino group, 2-ethylhexylamino group, nonylamino group, decylamino group, 3,7-dimethyloctylamino group, dodecyl amino group, cyclopentylamino group, dicyclopentylamino group, cyclohexylamino group, dicyclohexylamino group, ditrifluoromethylamino group, phenylamin
• the silyl group includes an unsubstituted silyl group and a silyl group substituted with one, two, or three substituents selected from an alkyl group, an aryl group, an arylalkyl group, and a monovalent aromatic heterocyclic group.
• Group hereinafter referred to as “substituted silyl group”.
• the substituent may have a secondary substituent.
• the number of carbon atoms of the substituted silyl group is usually 1 to 60, preferably 3 to 48, more preferably 3 to 40, not including the number of carbon atoms of the secondary substituent.
• substituted silyl group examples include trimethylsilyl group, triethylsilyl group, tripropylsilyl group, tri-isopropylsilyl group, dimethyl-isopropylsilyl group, diethyl-isopropylsilyl group, tert-butylsilyldimethylsilyl group, pentyldimethylsilyl group Hexyldimethylsilyl group, heptyldimethylsilyl group, octyldimethylsilyl group, 2-ethylhexyl-dimethylsilyl group, nonyldimethylsilyl group, decyldimethylsilyl group, 3,7-dimethyloctyl-dimethylsilyl group, dodecyldimethylsilyl group, Phenyl-C 1 -C 12 alkylsilyl group, C 1 -C 12 alkoxyphenyl-C 1 -C
• the substituted silyloxy group is one, two, or three substituents selected from the group consisting of an alkyl group, an aryl group, an arylalkyl group, an alkoxy group, an aryloxy group, an arylalkoxy group, and a monovalent heterocyclic oxy group.
• Means a silyloxy group substituted by The substituent may have a secondary substituent.
• the number of carbon atoms of the substituted silyloxy group is usually 1 to 60, preferably 3 to 48, not including the number of carbon atoms of the secondary substituent.
• substituted silyloxy group examples include trimethylsilyloxy group, triethylsilyloxy group, tripropylsilyloxy group, tri-isopropylsilyloxy group, dimethyl-isopropylsilyloxy group, diethyl-isopropylsilyloxy group, tert-butyldimethylsilyloxy group Group, pentyldimethylsilyloxy group, hexyldimethylsilyloxy group, heptyldimethylsilyloxy group, octyldimethylsilyloxy group, 2-ethylhexyl-dimethylsilyloxy group, nonyldimethylsilyloxy group, decyldimethylsilyloxy group, 3,7 - dimethyloctyl - butyldimethylsilyloxy group, dodecyl dimethyl silyl group, a phenyl -C 1 ⁇ C 12 alkyl si
• the substituted silylthio group is one, two, or three substituents selected from the group consisting of an alkyl group, an aryl group, an arylalkyl group, an alkylthio group, an arylthio group, an arylalkylthio group, and a monovalent heterocyclic thio group.
• a substituted silylthio group is meant.
• the substituent may have a secondary substituent.
• the number of carbon atoms of the substituted silylthio group is usually 1 to 60, preferably 3 to 48, not including the number of carbon atoms of the secondary substituent.
• substituted silylthio group examples include trimethylsilylthio group, triethylsilylthio group, tripropylsilylthio group, tri-isopropylsilylthio group, dimethyl-isopropylsilylthio group, diethyl-isopropylsilylthio group, tert-butyldimethylsilylthio group.
• the heterocyclic thio group means a group in which a hydrogen atom of a mercapto group is substituted with a monovalent aromatic heterocyclic group.
• Examples of the heterocyclic thio group include a heteroarylthio group (for example, a pyridylthio group, a pyridazinylthio group, a pyrimidylthio group, a pyrazinylthio group, and a triazinylthio group).
• the substituted silylamino group is one, two or three selected from the group consisting of an alkyl group, an aryl group, an arylalkyl group, an alkylamino group, an arylamino group, an arylalkylamino group and a monovalent heterocyclic amino group.
• a silylamino group substituted with a substituent is meant.
• the substituent may have a secondary substituent.
• the number of carbon atoms of the substituted silylamino group is usually 1 to 60, preferably 3 to 48, not including the number of carbon atoms of the secondary substituent.
• substituted silylamino group examples include trimethylsilylamino group, triethylsilylamino group, tripropylsilylamino group, tri-isopropylsilylamino group, dimethyl-isopropylsilylamino group, diethyl-isopropylsilylamino group, tert-butyldimethylsilylamino Group, pentyldimethylsilylamino group, hexyldimethylsilylamino group, heptyldimethylsilylamino group, octyldimethylsilylamino group, 2-ethylhexyl-dimethylsilylamino group, nonyldimethylsilylamino group, decyldimethylsilylamino group, 3,7 - dimethyloctyl - dimethylsilyl group, dodecyl dimethylsilyl group, a phenyl -C
• Acyl group means an unsubstituted acyl group and an acyl group substituted with a substituent such as a halogen atom.
• the number of carbon atoms of the acyl group is usually 1 to 20, preferably 2 to 18, more preferably 2 to 16, excluding the number of carbon atoms of the substituent.
• Examples of the acyl group include formyl group, acetyl group, propionyl group, butyryl group, isobutyryl group, pivaloyl group, benzoyl group, trifluoroacetyl group, and pentafluorobenzoyl group.
• Acyloxy group means an unsubstituted acyloxy group and an acyloxy group substituted with a substituent such as a halogen atom.
• the number of carbon atoms of the acyloxy group is usually 1 to 20, preferably 2 to 18, more preferably 2 to 16, excluding the number of carbon atoms of the substituent.
• Examples of the acyloxy group include formyloxy group, acetoxy group, propionyloxy group, butyryloxy group, isobutyryloxy group, pivaloyloxy group, benzoyloxy group, trifluoroacetyloxy group, and pentafluorobenzoyloxy group.
• the imine residue means a residue obtained by removing one hydrogen atom in the structure from an imine compound having a structure represented by at least one of the formula: H—N ⁇ C ⁇ and the formula: —N ⁇ CH—.
• Examples of the structure include aldimine; ketimine; a compound in which a hydrogen atom bonded to a nitrogen atom in aldimine is substituted with a substituent such as an alkyl group, aryl group, arylalkyl group, arylalkenyl group, and arylalkynyl group. Is mentioned.
• the number of carbon atoms of the imine residue is usually 2 to 20, preferably 2 to 18, more preferably 2 to 16, excluding the number of carbon atoms of the substituent.
• Examples of the imine residue include a general formula: —CR′ ⁇ N—R ′′ or a general formula: —N ⁇ C (R ′′) 2 (wherein R ′ represents a hydrogen atom, an alkyl group, an aryl group, Represents an arylalkyl group, an arylalkenyl group or an arylalkynyl group, and R ′′ represents an alkyl group, an aryl group, an arylalkyl group, an arylalkenyl group or an arylalkynyl group.
• two R ′ ' May be the same or different from each other.
• Two R ′′' s are bonded to each other to form a divalent group (for example, an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, and a hexamethylene group). Or an alkylene group having 2 to 18 carbon atoms, and a ring may be formed integrally with the remaining atomic groups.
• a divalent group for example, an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, and a hexamethylene group.
• an alkylene group having 2 to 18 carbon atoms, and a ring may be formed integrally with the remaining atomic groups.
• Examples of the imine residue include groups represented by the following structural formulas. (In the formula, Me represents a methyl group.)
• An amide group means a residue obtained by removing a hydrogen atom bonded to the nitrogen atom from an acid amide.
• an acid amide is a primary or secondary amide in which the hydrogen atom of ammonia is substituted by one or two acyl groups (except for a secondary amide having a cyclic structure, ie, an acid imide).
• the amide group means an unsubstituted amide group and an amide group substituted with a substituent such as a halogen atom.
• the number of carbon atoms of the amide group is usually 2 to 20, preferably 2 to 18, more preferably 2 to 16, excluding the number of carbon atoms of the substituent.
• amide group examples include a formamide group, an acetamide group, a propioamide group, a butyroamide group, a benzamide group, a trifluoroacetamide group, a pentafluorobenzamide group, a diformamide group, a diacetamide group, a dipropioamide group, a dibutyroamide group, a dibenzamide group, Examples include a ditrifluoroacetamide group and a dipentafluorobenzamide group.
• An acid imide group means a residue obtained by removing a hydrogen atom bonded to the nitrogen atom from an acid imide.
• An acid imide group means an unsubstituted acid imide group and a substituted acid imide group.
• the number of carbon atoms in the acid imide group is usually from 4 to 20, preferably from 4 to 18, more preferably from 4 to 16, excluding the number of carbon atoms of the substituent. Examples of the acid imide group include the following groups. (In the formula, Me represents a methyl group.)
• the carboxyl group is an unsubstituted carboxyl group and a carboxyl group substituted with a substituent such as an alkyl group, an aryl group, an arylalkyl group, and a monovalent aromatic heterocyclic group (hereinafter referred to as a substituted carboxyl group). Means.
• the substituent may have a secondary substituent.
• the number of carbon atoms of the substituted carboxyl group is usually 1 to 60, preferably 2 to 48, more preferably 2 to 45, not including the number of carbon atoms of the secondary substituent.
• Examples of the substituted carboxyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, an isopropoxycarbonyl group, a butoxycarbonyl group, an isobutoxycarbonyl group, a sec-butoxycarbonyl group, a tert-butoxycarbonyl group, and a pentyloxycarbonyl group.
• the divalent aromatic group means an atomic group obtained by removing two hydrogen atoms from either an aromatic hydrocarbon or an aromatic heterocyclic compound.
• the divalent aromatic group includes an unsubstituted divalent aromatic group and a substituted divalent aromatic group.
• Examples of the divalent aromatic group include an arylene group and a divalent aromatic heterocyclic group.
• Arylene group means an atomic group formed by removing two hydrogen atoms from an aromatic hydrocarbon.
• Arylene groups include those having an independent benzene ring or fused ring.
• An arylene group means an unsubstituted arylene group and a substituted arylene group.
• the number of carbon atoms of the arylene group is usually 6 to 60, preferably 6 to 48, more preferably 6 to 30, and further preferably 6 to 18. The number of carbon atoms does not include the number of carbon atoms of the substituent.
• the divalent aromatic heterocyclic group means an atomic group remaining after removing two hydrogen atoms directly bonded to an aromatic ring from an aromatic heterocyclic compound, and includes those having a condensed ring.
• examples of the heterocyclic compound having aromaticity are the same as those described for the monovalent aromatic heterocyclic group.
• the divalent aromatic heterocyclic group means an unsubstituted divalent aromatic heterocyclic group and a divalent aromatic heterocyclic group substituted with a substituent such as an alkyl group.
• the number average molecular weight in terms of polystyrene is 2 ⁇ 10 3 or more, preferably 2 ⁇ 10 3 to 1 ⁇ 10 8 , and preferably 1 ⁇ 10 4 to 1 ⁇ 10 6 .
• a compound having a polystyrene-equivalent number average molecular weight of 2 ⁇ 10 3 or more is referred to as a polymer compound.
• a compound having a polystyrene-reduced number average molecular weight of less than 2 ⁇ 10 3 is referred to as a low molecular compound.
• the number average molecular weight in terms of polystyrene is 2 ⁇ 10 3 or more, dendrimers and oligomers are also included in the polymer compound of the present invention.
• the polymer compound of the present invention contains a repeating unit represented by the formula (1) and a repeating unit represented by the formula (2). First, the repeating unit represented by formula (1) will be described.
• R 1 , R 2 , R 3 , R 4 and R 5 are each independently a hydrogen atom, alkyl group, alkoxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl.
• R 1 , R 2 , R 3 , R 4 and R 5 may be the same or different from each other. Of R 1 , R 2 , R 3 , R 4 and R 5 , adjacent groups may be bonded to form a ring.
• At least one of R 1 , R 2 , R 3 , R 4 and R 5 represents a group other than a hydrogen atom. At least one of R 1 , R 2 , R 3 , R 4 and R 5 is preferably a group containing an alkyl group.
• the group containing an alkyl group, a group containing an alkyl group itself, and the alkyl group as a part thereof e.g., alkoxy group, alkylthio group, substituted with and alkyl groups, mentioned as a candidate of the R 1 ⁇ R 5 Group).
• the group containing an alkyl group is preferably an alkyl group.
• the group containing an alkyl group is preferably an aryl group substituted with an alkyl group.
• the number of aliphatic carbon atoms constituting the alkyl group in the group containing the alkyl group is determined by the solubility in a solvent when the polymer compound of the present invention is used for the production of a light-emitting element and the lifetime of the light-emitting element obtained. Since it is compatible, it is preferably 6 or more, and more preferably 12 or more. In addition, since the lifetime and heat resistance of the light-emitting device obtained using the polymer compound of the present invention can be improved, the number of aliphatic carbon atoms is preferably 100 or less, more preferably 60 or less, More preferably, it is 30 or less. The number of aliphatic carbon atoms means the number of carbon atoms contained in the aliphatic skeleton portion of the target group.
• At least one of R 1 , R 2 , R 3 , R 4 and R 5 in the formula (1) is preferably an alkyl group having 6 or more carbon atoms, and has 12 or more carbon atoms.
• the alkyl group is more preferably.
• R 3 is more preferably an alkyl group having 12 or more carbon atoms. At least one of R 1 and R 5 is preferably a hydrogen atom. At least one of R 2 and R 4 is preferably an alkyl group, an aryl group, or an aryl group substituted with an alkyl group, and R 2 and R 4 are more preferably an aryl group substituted with an alkyl group. preferable.
• Ar 1 and Ar 2 are each independently an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, or an acyl group.
• examples of the divalent aromatic group include an arylene group and a divalent aromatic heterocyclic group.
• Examples of the arylene group represented by Ar 1 and Ar 2 include a phenylene group such as a 1,4-phenylene group, a 1,3-phenylene group and a 1,2-phenylene group; a 2,7-biphenylylene group and 3, Biphenylylene groups such as 6-biphenylylene group; naphthalene-diyl groups such as 1,4-naphthalene-diyl group, 1,5-naphthalene-diyl group and 2,6-naphthalene-diyl group; 1,4-anthracene-diyl group 1,5-anthracenediyl group, 2,6-anthracene-diyl group and anthracene-diyl group such as 9,10-anthracene-diyl group; phenanthrene-diyl group such as 2,7-phenanthrene-diyl group; Naphthacene diyl groups such as 7-nap
• the number of carbon atoms of the divalent aromatic heterocyclic group represented by Ar 1 and Ar 2 is usually 4 to 60, preferably 4 to 30, and more preferably not including the number of carbon atoms of the substituent. Is 6-12.
• the divalent aromatic heterocyclic group include pyridine-diyl groups such as 2,5-pyridine-diyl group and 2,6-pyridine-diyl group; thiophenes such as 2,5-thiophene-diyl group; Diyl group; furan-diyl group such as 2,5-furan-diyl group; quinoline-diyl group such as 2,6-quinoline-diyl group; 1,4-isoquinoline-diyl group and 1,5-isoquinoline diyl group Isoquinoline-diyl group; quinoxaline-diyl group such as 5,8-quinoxaline-diyl group; benzo [1,2,5] thiadiazole-diyl such
• At least one of Ar 1 and Ar 2 is an alkyl group, alkoxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkoxy group, arylalkylthio group, acyl group, acyloxy group, amide group, Acid imide group, imine residue, substituted silyl group, substituted silyloxy group, substituted silylthio group, monovalent aromatic heterocyclic group, heteroaryloxy group, heteroarylthio group, arylalkenyl group, arylalkynyl group, carboxyl group, And an arylene group or a divalent aromatic heterocyclic group which may have a substituent selected from the group consisting of cyano groups.
• Examples of the arylene group represented by Ar 1 and Ar 2 include a phenylene group (for example, the following formulas 1 to 3), a naphthalenediyl group (for example, the following formulas 4 to 13), and a biphenyl-diyl group (for example, the following formula 20-25), terphenyl-diyl groups (for example, the following formulas 26 to 28), phenanthrene-diyl groups (for example, the following formula 29), biphenylylene groups having a condensed ring (for example, the following formulas 31 and 32), indene- Diyl groups (for example, formulas 34 and 35), fluorene-diyl groups (for example, the following formulas 36 to 38), benzofluorene-diyl groups (for example, the following formulas A-1 to A-3) and dibenzofluorene-diyl groups ( For example, the following formula A-4) can be mentioned.
• a phenylene group for example
• R represents a hydrogen atom or a substituent.
• a plurality of R may be the same as or different from each other.
• examples of the substituent represented by R include an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, and an arylthio group.
• the hydrogen atom contained in these substituents may be substituted with a fluorine atom.
• At least one of a plurality of R is a group other than a hydrogen atom (that is, the above substituent).
• the substituent represented by R is preferably an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group or a monovalent aromatic heterocyclic group, More preferably, it is an alkyl group, an alkoxy group or an aryl group.
• Examples of the divalent aromatic heterocyclic group represented by Ar 1 and Ar 2 include a pyridine-diyl group (for example, the following formulas 45 to 50), a diazaphenylene group (for example, the following formulas 51 to 54), Quinolinediyl groups (for example, the following formulas 55 to 69), quinoxaline diyl groups (for example, the following formulas 70 to 74), bipyridyldiyl groups (for example, the following formulas 79 to 81), phenanthroline diyl groups (for example, the following formulas 82 to 84)
• a divalent aromatic heterocyclic group containing a nitrogen atom which is a hetero atom such as a group having a carbazole structure (for example, the following formulas 85 to 87); an oxygen atom, a silicon atom, a nitrogen atom, a sulfur atom and a selenium atom 5-membered aromatic heterocyclic groups containing heteroatoms such as the following (for example, the following formulas
• R represents a hydrogen atom or a substituent.
• a plurality of R may be the same as or different from each other.
• examples of the substituent represented by R are the same as the examples of the substituent represented by R in the formula 1.
• at least one of a plurality of R is a group other than a hydrogen atom (that is, the above-described substitution). Group).
• At least one of Ar 1 and Ar 2 is preferably a divalent aromatic group represented by the following formula (3) or (4)
• Ar 1 and Ar 2 are, each independently, the following equation (3 Or a divalent aromatic group represented by (4).
• an unsubstituted divalent aromatic group represented by the following formula (3) is more preferable.
• R ′ represents a hydrogen atom or an alkyl group.
• divalent aromatic group represented by the formula (3) examples include divalent groups represented by the following formulas 3-1 to 3-15. (In the formula, Me represents a methyl group.)
• divalent aromatic group represented by the formula (4) examples include divalent groups represented by the following formulas 4-1 to 4-14. (In the formula, Me represents a methyl group, and t-Bu represents a tert-butyl group.)
• the repeating unit represented by the formula (1) may be contained alone or in combination of two or more in the polymer compound of the present invention.
• repeating unit represented by the formula (1) include repeating units represented by the following formulas 1-1 to 1-52.
• Ar 3 represents an aryl group or a monovalent aromatic heterocyclic group.
• Ar 3 is preferably an aryl group because the lifetime of the light-emitting device obtained using the polymer compound of the present invention can be improved.
• Ar 4 represents a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, an acyl group, an acyloxy group, Amide group, acid imide group, imine residue, substituted amino group, substituted silyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group, monovalent aromatic heterocyclic group, heteroaryloxy group, heteroarylthio group, An arylalkenyl group, an arylalkynyl group, a substituted carboxyl group, or a cyano group is represented.
• Ar 4 is preferably a hydrogen atom, an alkyl group, an aryl group or a monovalent aromatic heterocyclic group, and more preferably a hydrogen atom, an alkyl group
• R 6 represents an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, an acyl group, an acyloxy group, an amide group, Acid imide group, imine residue, substituted amino group, substituted silyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group, monovalent aromatic heterocyclic group, heteroaryloxy group, heteroarylthio group, arylalkenyl group Represents an arylalkynyl group, a substituted carboxyl group, or a cyano group. When a plurality of R 6 are present, they may be the same or different.
• a 0 or 1.
• Two a's may be the same or different.
• a repeating unit represented by the formula (2) a repeating unit represented by the following formula (20) is preferable.
• Ar 3 and Ar 4 are as defined for Ar 3 and Ar 4 of formula (2).
• Ar 4 is preferably a hydrogen atom, an alkyl group, an aryl group, or a monovalent aromatic heterocyclic group, and more preferably a hydrogen atom, an alkyl group, or an aryl group.
• the aryl group has a substituent having 2 or more carbon atoms. It is preferable to have.
• Examples of the repeating unit represented by the formula (20) include repeating units represented by the following formulas 1e to 8e. (In the formula, n-Bu represents an n-butyl group, and t-Bu represents a tert-butyl group.)
• the repeating unit represented by the formula (2) may be contained alone or in combination of two or more in the polymer compound of the present invention.
• the ratio of the repeating unit represented by the formula (1) to the total repeating units constituting the polymer compound of the present invention is preferably larger from the viewpoint of electron transportability (that is, to improve electron transportability), From the viewpoint of the lifetime of the light-emitting element obtained when the polymer compound is used for production of a light-emitting element, a smaller one is preferable. Therefore, the ratio is preferably 10 mol% or more and 30 mol% or less, more preferably 10 mol% or more and 20 mol% or less, and particularly preferably 10 mol% or more and 15 mol% or less.
• the ratio of the repeating unit represented by the formula (2) with respect to all repeating units constituting the polymer compound of the present invention is the thermal stability and when the polymer compound is used for the production of a light emitting device. Since the lifetime of the light-emitting element obtained can be improved, it is preferably 20 mol% or more. The upper limit of the ratio is not particularly limited, but is usually 75 mol% or less.
• the total ratio of the repeating unit represented by the formula (1) and the repeating unit represented by the formula (2) with respect to all repeating units constituting the polymer compound of the present invention is determined using the polymer compound of the present invention. Since the electron transport property and lifetime of the light-emitting element to be obtained can be improved, the content is preferably 30 mol% or more, more preferably 40 mol% or more, and particularly preferably 50 mol% or more.
• the polymer compound of the present invention may further contain a repeating unit represented by the following formula (5).
• Ar 5 represents an arylene group or a divalent aromatic heterocyclic group.
• arylene group for Ar 5 are the same as the arylene groups described above for Ar 1 and Ar 2 .
• divalent aromatic heterocyclic group for Ar 5 are the same as the divalent aromatic heterocyclic group described above for Ar 1 and Ar 2 .
• Ar 6 and Ar 7 are each independently an alkyl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, an acyl group, or an acyloxy group.
• a substituted carboxyl group or a cyano group is represented.
• R 7 is an alkyl group, alkoxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkoxy group, arylalkylthio group, acyl group, acyloxy group, amide group, acid imide group, imine residue Group, substituted amino group, substituted silyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group, monovalent aromatic heterocyclic group, heteroaryloxy group, heteroarylthio group, arylalkenyl group, arylalkynyl group, substituted Represents a carboxyl group or a cyano group. It is preferable that at least one of Ar 6 and Ar 7 is a hydrogen atom or an alkyl group, since the solubility of the polymer compound of the present invention in a solvent and the lifetime of the obtained light-emitting element can be improved.
• a 0 or 1.
• Two a's may be the same or different.
• R 7 When a plurality of R 7 are present, they may be the same or different.
• Examples of the repeating unit represented by the formula (5) further include a repeating unit represented by the following formula (7) and a repeating unit represented by the following formula (8).
• R 8 and R 9 are each independently an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, or an acyl group.
• R 8 and R 9 may be the same or different from each other.
• R 8 and R 9 are each independently an alkyl group, an aryl group, or a monovalent aromatic, from the viewpoint of the balance between the heat resistance of the polymer compound of the present invention and the solubility in an organic solvent. It is preferably a heterocyclic group, an alkoxy group, an aryloxy group, an arylalkyl group or a substituted amino group, more preferably an alkyl group or an arylalkyl group, still more preferably an alkyl group, a propyl group, an isopropyl group Group, butyl group, sec-butyl group, isobutyl group, pentyl group, isoamyl group, hexyl group, cyclohexyl group, heptyl group, octyl group, 2-ethylhexyl group, cyclohexylmethyl group, nonyl group, decyl group, 3,7- A dimethyloctyl group or a
• R 10 and R 11 are each independently an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, or an acyl group.
• R 10 and R 11 may be the same or different from each other.
• R 10 and R 11 is an alkyl group, an aryl group, a monovalent aromatic complex from the viewpoint of the balance between the heat resistance of the polymer compound of the present invention and the solubility in an organic solvent. It is preferably a cyclic group, an arylalkyl group or an amino group, more preferably an alkyl group, an aryl group, a monovalent aromatic heterocyclic group or an amino group, an alkyl group, an aryl group or a monovalent aromatic group. It is more preferably a heterocyclic group, and particularly preferably an alkyl group or an aryl group. R 10 and R 11 may be the same or different from each other.
• b 0 or 1.
• Examples of the repeating unit represented by the formula (7) include repeating units represented by the following formulas 7-001 to 7-019 and 7-101 to 7-105.
• Examples of the repeating unit represented by the formula (8) include repeating units represented by the following formulas 8-001 to 8-017, 8-101 to 8-113, and 8-201 to 8-208.
• Me represents a methyl group
• Et represents an ethyl group
• i-Pr represents an isopropyl group
• n-Bu represents an n-butyl group
• t-Bu represents a tert-butyl group.
• the repeating unit represented by formula (5) may be contained alone or in combination of two or more in the polymer compound of the present invention.
• the polymer compound of the present invention is represented by the repeating unit represented by the formula (5), the repeating unit represented by the formula (6), the repeating unit represented by the formula (7), and the formula (8).
• One type of repeating unit selected from repeating units or a combination of two or more types of repeating units may be included.
• the repeating unit represented by Formula (6), the repeating unit represented by Formula (7), and the repeating unit represented by Formula (8) are each Two or more types may be combined and contained in the polymer compound of the present invention.
• the proportion of the repeating unit represented by the formula (5) with respect to all repeating units constituting the polymer compound of the present invention is usually 0 mol% or more and 80 mol% or less, and 5 mol% or more and 70 mol% or less. It is preferably 10 mol% or more and 60 mol% or less, more preferably 10 mol% or more and 50 mol% or less.
• the total ratio of the repeating unit represented by the formula (1), the repeating unit represented by the formula (2), and the repeating unit represented by the formula (5) with respect to all the repeating units is 80 mol% or more. Preferably, it is 85 mol% or more, more preferably 90 mol% or more.
• the polymer compound of the present invention preferably further contains a repeating unit represented by the following formula (9).
• Ar 8 , Ar 9 , Ar 10 and Ar 14 each independently represent an arylene group or a divalent aromatic heterocyclic group.
• Ar 11 , Ar 12 and Ar 13 each independently represent an aryl group or a monovalent aromatic heterocyclic group.
• Ar 8 , Ar 9 , Ar 10 , Ar 11 , Ar 12 , Ar 13 and Ar 14 may each independently have a substituent.
• x and y are each independently 0 or 1. However, the value of x + y is 0 or 1.
• examples of the substituent include an alkyl group, an alkoxy group, an aryl group, Aryloxy group, arylalkyl group, arylalkoxy group, arylalkenyl group, arylalkynyl group, amino group, substituted amino group, halogen atom, acyl group, acyloxy group, monovalent aromatic heterocyclic group, carboxyl group, nitro group And an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an arylalkyl group, an arylalkoxy group, a substituted amino group, an acyl group or a cyano group, more preferably an alkyl group, An alkoxy group or an aryl group.
• examples of the arylene group represented by Ar 8 , Ar 9 , Ar 10 and Ar 14 include a 1,3-phenylene group, a 1,4-phenylene group, a 1,4-naphthalenediyl group, Examples include 2,6-naphthalenediyl group, 9,10-anthracenediyl group, 2,7-phenanthenediyl group, 5,12-naphthacenediyl group, and 2,7-fluorenediyl group.
• the number of carbon atoms of the divalent aromatic heterocyclic group represented by Ar 8 , Ar 9 , Ar 10 and Ar 14 does not include the number of carbon atoms of the substituent, and is usually 4 to 60, preferably 4 to 20, and more preferably 4 to 9.
• the divalent aromatic heterocyclic group include 2,5-thiophenediyl group, N-methyl-2,5-pyrrolediyl group, 2,5-furandiyl group, and benzo [2,1,3] thiadiazole. Examples include -4,7-diyl, 3,7-phenoxazinediyl group and 3,6-carbazolediyl group.
• examples of Ar 8 , Ar 9 , Ar 10 and Ar 14 include divalent groups represented by the following formulas 1b to 3b.
• Ar 8 and Ar 10 are preferably arylene groups, more preferably 1,3-phenylene groups, 1,4-phenylene groups, 1,4-naphthalenediyl groups, 2,6 A naphthalenediyl group or a group represented by the above formula 1b, more preferably a 1,4-phenylene group or a 1,4-naphthalenediyl group, and particularly preferably a 1,4-phenylene group.
• Ar 9 is preferably 1,3-phenylene group, 1,4-phenylene group, 1,4-naphthalenediyl group, 2,7-fluorenediyl group, benzo [2,1, 3] a thiadiazole-4,7-diyl group, a 3,7-phenoxazinediyl group, or a group represented by the formula 1b, preferably a 1,4-phenylene group, a 1,4-naphthalenediyl group, A 2,7-fluorenediyl group or a group represented by the formula 1b, more preferably a 1,4-phenylene group or a group represented by the formula 1b.
• Ar 11 , Ar 12 and Ar 13 are each independently preferably an alkyl group, an aryl group or a monovalent aromatic heterocyclic group, more preferably an alkyl group or an aryl group. Group, more preferably an aryl group.
• R 21 represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an arylalkyl group, an arylalkoxy group, an arylalkenyl group, an arylalkynyl group, an amino group, or a substituted amino group.
• a plurality of R 21 may be the same or different.
• a repeating unit represented by the following formula (10) is preferable.
• R 31 , R 41 and R 51 each independently represents an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or a phenylalkyl group having 7 to 26 carbon atoms.
• Phenylalkoxy group having 7 to 26 carbon atoms, phenyl group, phenoxy group, alkylphenyl group having 7 to 26 carbon atoms, alkoxyphenyl group having 7 to 26 carbon atoms, alkylcarbonyl group having 2 to 21 carbon atoms Represents a formyl group, an alkoxycarbonyl group having 2 to 21 carbon atoms, or a carboxyl group.
• R 31 and R 41 may be combined to form a ring instead of representing the above group.
• R 31 and R 41 may be the same or different.
• R 41 may be the same or different, and a plurality of R 51 are present. They may be the same or different.
• s and t are each independently an integer of 0 to 4.
• u is 1 or 2.
• v is an integer of 0 to 5.
• examples of the ring include a C 5 to C 14 heterocyclic ring which may have a substituent.
• examples of the heterocyclic ring include a morpholine ring, a thiomorpholine ring, a pyrrole ring, a piperidine ring, and a piperazine ring.
• Examples of the repeating unit represented by the formula (10) include repeating units represented by the following formulas 1d to 10d.
• the ratio of the repeating unit represented by the formula (5) to all repeating units constituting the polymer compound of the present invention is usually 0 mol% or more and 20 mol% or less, and 0 mol% or more and 10 mol% or less. Preferably there is.
• the repeating unit represented by Formula (1), the repeating unit represented by Formula (2), the repeating unit represented by Formula (5), and the repeating unit represented by Formula (9) with respect to all the repeating units. Is preferably 90 mol% or more, more preferably 95 mol% or more, still more preferably 99 mol% or more, and 100 mol% (excluding inevitable impurities). It is particularly preferred.
• the polymer compound of the present invention can be produced, for example, by condensation polymerization.
• condensation polymerization method examples include polymerization by the Suzuki reaction (Chem. Rev., 95, 2457 (1995)), polymerization by the Grignard reaction (Kyoritsu Shuppan, Polymer Functional Material Series Volume 2, Polymer Synthesis and Reaction (2), pp. 432-433), Polymerization by Yamamoto Coupling Reaction (Prog. Polym.
• the polymer compound can be produced, for example, by subjecting a compound represented by the formula: Y 3 —W 1 —Y 4 and a compound represented by the formula: Y 5 —W 2 —Y 6 to condensation polymerization.
• W 1 and W 2 each independently represent a repeating unit represented by the formula (1), the formula (2), the formula (5) or the formula (9).
• Y 3 , Y 4 , Y 5 and Y 6 each independently represent a polymerization reactive group.
• the polymer compound of the present invention has a repeating unit other than those described above, it may be subjected to condensation polymerization in the presence of a compound having two polymerizable reactive groups that become repeating units other than those described above.
• Examples of the polymerization reactive group include a halogen atom, an alkyl sulfonate group, an aryl sulfonate group, an aryl alkyl sulfonate group, a boric acid ester residue, a sulfonium methyl group, a phosphonium methyl group, a phosphonate methyl group, a monohalogenated methyl group, and boric acid.
• Examples thereof include a residue (—B (OH) 2 ), a formyl group, a cyano group, and a vinyl group.
• halogen atom that is the polymerization reactive group
• examples of the halogen atom that is the polymerization reactive group include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
• alkyl sulfonate group that is the polymerization reactive group examples include a methane sulfonate group, an ethane sulfonate group, and a trifluoromethane sulfonate group.
• aryl sulfonate group that is the polymerization reactive group examples include a benzene sulfonate group and a p-toluene sulfonate group.
• arylalkyl sulfonate group that is the polymerization reactive group
• examples of the arylalkyl sulfonate group that is the polymerization reactive group include a benzyl sulfonate group.
• boric acid ester residue that is the polymerization reactive group examples include groups represented by the following formulae. (In the formula, Me represents a methyl group, and Et represents an ethyl group.)
• Examples of the sulfonium methyl group that is the polymerization reactive group include groups represented by the following formula. -CH 2 S + Me 2 X 0- , -CH 2 S + Ph 2 X 0- (In the formula, X 0 represents a halogen atom and Ph represents a phenyl group.)
• Examples of the phosphonium methyl group that is the polymerization reactive group include groups represented by the following formulas. -CH 2 P + Ph 3 X 0- (In the formula, X 0 represents a halogen atom.)
• Examples of the phosphonate methyl group that is the polymerization reactive group include groups represented by the following formulas. -CH 2 PO (OR ′′) 2 (In the formula, R ′′ represents an alkyl group or an aryl group.)
• Examples of the monohalogenated methyl group that is the polymerization reactive group include a methyl fluoride group, a methyl chloride group, a methyl bromide group, and a methyl iodide group.
• the polymerization-reactive group is, for example, a halogen atom, an alkyl sulfonate group, an aryl sulfonate group, an aryl alkyl sulfonate group, or the like when using a zerovalent nickel complex such as a Yamamoto coupling reaction, and a Suzuki coupling reaction or the like.
• a nickel catalyst or a palladium catalyst an alkyl sulfonate group, a halogen atom, a boric acid ester residue, a boric acid residue, or the like.
• the polymerization reactive group includes a halogen atom, an alkyl sulfonate group, an aryl sulfonate group, an aryl alkyl sulfonate group, a boric acid residue, and A total (J) of the number of moles of halogen atoms, alkyl sulfonate groups, aryl sulfonate groups and arylalkyl sulfonate groups selected from one or more groups consisting of borate ester residues and possessed by all raw material compounds; ,
• the ratio of the total number of moles of boric acid residues and boric acid ester residues (K) is substantially 1 (usually K / J is 0.7 to 1.2), and the nickel catalyst or palladium catalyst A production method in which condensation polymerization is performed is preferred.
• Examples of the combination of the starting compounds include dihalogenated compounds, bis ( Examples thereof include a combination of an alkyl sulfonate) compound, a bis (aryl sulfonate) compound or a bis (aryl alkyl sulfonate) compound and a diboric acid compound or a diboric acid ester compound.
• the above compounds include halogen-boric acid compounds, halogen-boric acid ester compounds, alkyl sulfonate-boric acid compounds, alkyl sulfonate-boric acid ester compounds, aryl sulfonates— Boric acid compounds, aryl sulfonate-boric acid ester compounds, arylalkyl sulfonate-boric acid compounds, arylalkyl sulfonate-boric acid compounds, arylalkyl sulfonate-boric acid ester compounds, and the like may be used.
• the compound that yields the repeating unit represented by the formula (1) is preferably a compound represented by the following formula (i).
• R a , R f and R g each independently represent a hydrogen atom or an alkyl group
• R b , R c , R d and R e are each independently an alkyl group or an alkyl group.
• Ar 1 and Ar 2 each independently represents an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, Acyl group, acyloxy group, amide group, acid imide group, imine residue, substituted silyl group, substituted silyloxy group, substituted silylthio group, monovalent aromatic heterocyclic group, heteroaryloxy group, heteroarylthio group, arylalkenyl Having a substituent selected from the group consisting of a group, an arylalkynyl group, a substituted carboxyl group, and a cyano group.
• X represents a halogen atom, a boric acid ester residue, a boric acid residue, a group represented by the following formula (a-1), or a group represented by the following formula (a-2).
• RT represents an alkyl group or an aryl group, and may have a substituent.
• X A represents a halogen atom.
• X A has the same meaning as described above.
• R T is, R T present .3 pieces of the same meaning as described above may be the same or different.
• the organic solvent used for the condensation polymerization is sufficiently subjected to deoxygenation treatment and dehydration treatment in order to suppress side reactions.
• this is not the case in the case of reaction in a two-phase system with water such as Suzuki coupling reaction.
• organic solvent used in the condensation polymerization examples include saturated hydrocarbons such as pentane, hexane, heptane, octane, and cyclohexane, unsaturated hydrocarbons such as benzene, toluene, ethylbenzene, and xylene, carbon tetrachloride, chloroform, dichloromethane, chlorobutane, Halogenated saturated hydrocarbons such as bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane, halogenated unsaturated hydrocarbons such as chlorobenzene, dichlorobenzene, trichlorobenzene, methanol, ethanol, propanol, isopropanol Alcohols such as butanol and tert-butyl alcohol, carboxylic acids such as formic acid, a
• an alkali and / or a catalyst may be added to accelerate the reaction.
• the alkali and catalyst are preferably those that are sufficiently dissolved in the solvent used in the reaction.
• To mix the alkali and / or catalyst slowly add the alkali or catalyst solution while stirring the reaction solution under an inert atmosphere such as argon or nitrogen, or conversely, add the alkali and / or catalyst solution to the alkali and / or catalyst solution. What is necessary is just to add a reaction liquid slowly.
• the polymer compound of the present invention When the polymer compound of the present invention is used for the production of a light-emitting device or the like, its purity affects the performance of the light-emitting device such as the light-emitting properties. Polymerization is preferred after purification by the method. Further, after the polymerization, it is preferable to carry out a purification treatment such as purification by reprecipitation and fractionation by chromatography.
• composition of the present invention contains the polymer compound of the present invention and at least one material selected from the group consisting of a hole transport material, an electron transport material and a light emitting material.
• Examples of the light emitting material include a low molecular fluorescent light emitting material, a light emitting organometallic complex compound, and a polymer fluorescent light emitting material.
• the host material preferably has a high minimum triplet excitation energy. Therefore, in the composition of the present invention, when a light-emitting organometallic complex compound that emits red light having a light emission peak wavelength of 600 nm or more is used as the light-emitting material, the polymer compound of the present invention contained in the composition contains It is preferable that the repeating unit represented by the formula (5) further includes a repeating unit represented by the formula (6).
• the polymer compound of the present invention contained in the composition is
• the repeating unit represented by the formula (5) further includes a repeating unit selected from the group consisting of the repeating unit represented by the formula (7) and the repeating unit represented by the formula (8). preferable.
• the emission peak wavelength of the luminescent metal complex compound is evaluated by, for example, dissolving the compound in an organic solvent such as xylene, toluene and chloroform, preparing a diluted solution, and measuring the PL spectrum of the diluted solution. obtain.
• Examples of the light-emitting organometallic complex compound include known compounds such as triplet light-emitting complexes, compounds conventionally used as light-emitting materials for low-molecular organic EL devices, and Nature, (1998), 395. 151, Appl. Phys. Lett. (1999), 75 (1), 4, Proc. SPIE-Int. Soc. Opt. Eng. (2001), 4105 (Organic Light-Emitting Materials and Devices IV), 119, J. MoI. Am. Chem. Soc. , (2001), 123, 4304, Appl. Phys. Lett. , (1997), 71 (18), 2596, Syn. Met. , (1998), 94 (1), 103, Syn. Met.
• the light-emitting organometallic complex compound is a square of the orbital coefficient of the outermost shell d orbit of the central metal in the highest occupied molecular orbital (HOMO) of the metal complex.
• Is preferably a compound in which the ratio of the sum of to the sum of the squares of all atomic orbital coefficients is 1/3 or more.
• the compound include ortho-metalated complexes in which the central metal is a transition metal belonging to the sixth period of the periodic table.
• the central metal of the light-emitting organometallic complex compound has, for example, an atomic number of 50 or more, can exhibit spin-orbit interaction with the complex, and causes an intersystem crossing between the singlet state and the triplet state.
• the metal obtained is mentioned.
• the central metal is preferably gold, platinum, iridium, osmium, rhenium, tungsten, europium, terbium, thulium, dysprosium, samarium, praseodymium, gadolinium or ytterbium, more preferably gold, platinum, iridium, It is osmium, rhenium or tungsten, more preferably gold, platinum, iridium, osmium or rhenium, particularly preferably gold, platinum, iridium or rhenium, particularly preferably platinum or iridium.
• Examples of the ligand of the light-emitting organometallic complex compound include 8-quinolinol and derivatives thereof, benzoquinolinol and derivatives thereof, and 2-phenyl-pyridine and derivatives thereof.
• an alkyl group which may have a substituent, an alkoxy group which may have a substituent, a substituent Having a substituent selected from the group consisting of an aryl group which may have a substituent and a heteroaryl group which may have a substituent (hereinafter referred to as a “ligand substituent”).
• the total number of atoms other than hydrogen atoms contained in the ligand substituent is preferably 3 or more, more preferably 5 or more, further preferably 7 or more, and 10 or more. It is particularly preferred.
• a ligand substituent exists for every ligand, The kind may be the same for each ligand, or may differ.
• an organometallic complex compound having a structure represented by the following formula (11) is preferably exemplified.
• R 1p , R 2p , R 3p , R 4p , R 5p , R 6p , R 7p and R 8p each independently represent a hydrogen atom or an aryl group.
• the portion represented by represents a monoanionic bidentate ligand.
• R x and R y are atoms coordinated to the central metal Ir, and each independently represents a carbon atom, an oxygen atom, or a nitrogen atom.
• m represents an integer of 1 to 3
• n represents an integer of 0 to 2.
• Examples of the monoanionic bidentate ligand include monoanionic groups in which the arc portion connecting R x and R y in formula (11) is a divalent group having 3 to 30 atoms other than hydrogen atoms.
• the bidentate ligand is preferably, for example, a ligand having a structure represented by the following formula. (In the formula, * indicates the position of the coordination atom.)
• the ligand shown on the left side and the ligand shown on the right side may each independently have the ligand substituent, and the solubility in a solvent can be improved. It preferably has the ligand substituent.
• the following compounds are preferable as the light-emitting organometallic complex compound having an emission peak wavelength of 500 nm or more and less than 600 nm.
• tBu represents a tert-butyl group
• R represents a hydrogen atom or a substituent.
• a plurality of R may be the same or different.
• a compound having a structure represented by the following formula (12), (12-1) or (12-2) is preferably used as the luminescent organometallic complex compound exhibiting a red luminescent color having an emission peak wavelength of 600 nm or more. Illustrated.
• R 9p , R 10p , R 11p , R 12p , R 13p , R 14p , R 15p , R 16p , R 17p , R 18p , R 19p , R 20p , R 21p , R 22p , R 23p , R 24p and R 25p are each independently a hydrogen atom, halogen atom, alkyl group, alkoxy group, alkylthio group, aryl group, aryloxy group, arylthio group, aryl Alkyl group, arylalkoxy group, arylalkylthio group, acyl group, acyloxy group, amide group, acid imide group, imine residue, substituted amino group, substituted silyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group, monovalent Represents an aromatic heterocyclic group, a heteroaryloxy group, a hetero
• Z 1 , Z 2 , Z 3 , Z 4 and Z 5 each independently represent —C (R * ) ⁇ or a nitrogen atom.
• R * represents a hydrogen atom or a substituent.
• R 9p , R 10p , R 11p , R 12p , R 13p , R 14p , R 15p , R 16p , R 17p , R 18p , R 19p , R 20p , R 21p , R 22p , R 23p , R 24p , R 25p , Z 1 , Z 2 , Z 3 , Z 4 and Z 5 are the same or different when there are a plurality of each. May be. However, at least two of Z 1 , Z 2 , Z 3 , Z 4 and Z 5 are nitrogen atoms.
• the following compounds are preferable as the light-emitting organometallic complex compound having a light emission peak wavelength of 600 nm or more.
• tBu represents a tert-butyl group
• Me represents a methyl group.
• the luminescent organometallic complex compounds may be used alone or in combination of two or more.
• the low-molecular fluorescent material is usually a material having a maximum peak of fluorescent emission in a wavelength range of 400 nm to 700 nm.
• the molecular weight is usually less than 3000, preferably 100 to 2000, and more preferably 100 to 1000.
• the low-molecular fluorescent material may be any material known as a light-emitting material for organic EL elements.
• Examples of the low-molecular fluorescent material include naphthalene derivatives, anthracene and derivatives thereof, perylene and derivatives thereof, quinacridone derivatives, xanthene dyes, coumarin dyes, cyanine dyes, triphenylamine derivatives, oxadiazole derivatives, pyrazolo derivatives.
• Dye-based materials such as quinoline derivatives, distyrylbenzene derivatives, distyrylarylene derivatives, pyrrole derivatives, thiophene ring compounds, pyridine ring compounds, and oligothiophene derivatives; aluminum quinolinol complexes, benzoquinolinol beryllium complexes, benzoxazolyl zinc complexes,
• the central metal such as benzothiazole zinc complex, azomethyl zinc complex, porphyrin zinc complex, and europium complex has Al, Zn, Be, or a rare earth metal (eg, Tb, Eu, Dy, etc.), etc.
• polymeric fluorescent material examples include polyparaphenylene vinylene derivatives, polythiophene derivatives, polyparaphenylene derivatives, polysilane derivatives, polyacetylene derivatives, polyfluorene derivatives, polyvinylcarbazole derivatives, and dye-based materials exemplified in the low molecular fluorescent materials. And a chromophore containing.
• the ratio of “at least one material selected from the group consisting of a hole transport material, an electron transport material and a light emitting material” to the polymer compound is 100 parts by weight of the polymer compound.
• “At least one material selected from the group consisting of a hole transport material, an electron transport material and a light emitting material” is usually set to be 0.01 to 400 parts by weight for each material, preferably It is set to be 0.05 to 150 parts by weight.
• the hole transport material may be any material known as a hole transport material for organic EL elements.
• the hole transport material include polyvinyl carbazole and derivatives thereof; polysilane and derivatives thereof; polysiloxane derivatives having an aromatic amine in the side chain or main chain; pyrazoline derivatives; arylamine derivatives; stilbene derivatives; Polythiophene and derivatives thereof; polyarylamine and derivatives thereof; polypyrrole and derivatives thereof; poly (p-phenylene vinylene) and derivatives thereof; poly (2,5-thienylene vinylene) and derivatives thereof.
• the hole transport material may have an arylene group or a divalent aromatic heterocyclic group as a copolymerization component (structural unit).
• the electron transport material may be any material known as an electron transport material for organic EL elements.
• the electron transport material include oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, fluorenone derivatives, Examples include diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and its derivatives, triaryltriazine and its derivatives, polyquinoline and its derivatives, polyquinoxaline and its derivatives, polyfluorene and its derivatives.
• the electron transport material may have an arylene group or a divalent aromatic heterocyclic group as a copolymerization component (structural unit).
• each component may be used individually by 1 type, or may use 2 or more types together.
• the liquid composition of the present invention comprises the polymer compound of the present invention and a solvent or dispersion medium.
• the solvent or dispersion medium used in the liquid composition of the present invention can be selected from known solvents that can uniformly dissolve or disperse the components of the thin film and are stable.
• a solvent include the following.
• Aromatic hydrocarbon solvents toluene, xylene (each isomer or a mixture thereof), 1,2,3-trimethylbenzene, 1,2,4-trimethylbenzene, mesitylene (1,3,5-trimethylbenzene), Ethylbenzene, propylbenzene, isopropylbenzene, butylbenzene, isobutylbenzene, 2-phenylbutane, tert-butylbenzene, pentylbenzene, neopentylbenzene, isoamylbenzene, hexylbenzene, cyclohexylbenzene, heptylbenzene, octylbenzene, 3-propyltoluene 4-propy
• Aliphatic hydrocarbon solvents n-pentane, n-hexane, cyclohexane, methylcyclohexane, n-heptane, n-octane, n-nonane, n-decane, decalin and the like.
• Aromatic ether solvents anisole, ethoxybenzene, propoxybenzene, butyroxybenzene, pentyloxybenzene, cyclopentyloxybenzene, hexyloxybenzene, cyclohexyloxybenzene, heptyloxybenzene, octyloxybenzene, 2-methylanisole, 3-methyl Anisole, 4-methylanisole, 4-ethylanisole, 4-propylanisole, 4-butylanisole, 4-pentylanisole, 4-hexylanisole, diphenylether, 4-methylphenoxybenzene, 4-ethylphenoxybenzene, 4-propylphenoxy Benzene, 4-butylphenoxybenzene, 4-pentylphenoxybenzene, 4-hexylphenoxybenzene, 4-phenoxytoluene, 3-phenyl Nokishitoruen, 1,3-dimethoxybenzene, 2,6-dimethyl
• Aliphatic ether solvents tetrahydrofuran, dioxane, dioxolane and the like.
• Ketone solvents acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, acetophenone, and the like.
• Ester solvents ethyl acetate, butyl acetate, methyl benzoate, ethyl cellosolve acetate and the like.
• Chlorinated solvents methylene chloride, chloroform, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o-dichlorobenzene, and the like.
• Alcohol solvents methanol, ethanol, propanol, isopropanol, cyclohexanol, phenol and the like.
• Polyhydric alcohol and its derivatives ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, and 1,2- Hexanediol and the like.
• Aprotic polar solvents dimethyl sulfoxide, N-methyl-2-pyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide and the like.
• solvents may be used alone or in combination of two or more.
• a mixed solvent it is preferable to combine two or more of the above solvent groups. In that case, one or more of the solvent groups of different systems may be combined even if a plurality of solvent groups of the same system are selected and combined. You may select and combine.
• the composition ratio of the mixed solvent can be determined in consideration of the physical properties of each solvent and the solubility of the polymer compound and the like.
• a mixed solvent obtained by selecting and combining a plurality of solvents from the same solvent group a mixed solvent selected by combining a plurality of aromatic hydrocarbon solvents and a combination of selected from an aromatic ether solvent are combined. And a mixed solvent.
• the mixed solvent obtained by selecting and combining one or more kinds from different solvent groups include the following combinations. Combination of aromatic hydrocarbon solvent and aliphatic hydrocarbon solvent, combination of aromatic hydrocarbon solvent and aromatic ether solvent, combination of aromatic hydrocarbon solvent and aliphatic ether solvent, aromatic hydrocarbon Combinations of system solvents and aprotic polar solvents, combinations of aromatic ether solvents and aprotic polar solvents, and the like.
• a single solvent or a mixed solvent containing an organic solvent having a structure containing a benzene ring, a melting point of 0 ° C. or less, and a boiling point of 100 ° C. or more is preferable.
• a single solvent or a mixed solvent containing a hydrocarbon solvent or an aromatic ether solvent is preferred.
• the solvent may be a single solvent or a mixed solvent, but it is preferable to use a mixed solvent from the viewpoint of film formability.
• a solvent purified by a purification method such as washing, distillation, and contact with an adsorbent may be used.
• an organic thin film containing the polymer compound can be easily produced.
• an organic thin film containing the polymer compound can be obtained by applying the liquid composition of the present invention on a substrate and distilling off the solvent by heating, blowing, or reducing pressure.
• the conditions for distilling off the solvent can be changed according to the organic solvent used. Examples of the conditions include an atmospheric temperature (heating atmosphere) of about 50 to 150 ° C. and a reduced pressure atmosphere of about 10 ⁇ 3 Pa.
• the suitable viscosity of the liquid composition of the present invention varies depending on the printing method, but at 25 ° C., it is preferably 0.5 to 1000 mPa ⁇ s, more preferably 0.5 to 500 mPa ⁇ s. Further, when the liquid composition passes through a discharge device as in the ink jet printing method, the viscosity at 25 ° C. of the liquid composition is preferably 0.5 to in order to prevent clogging and flight bending at the time of discharge. 50 mPa ⁇ s, more preferably 0.5 to 20 mPa ⁇ s.
• the content of the polymer compound of the present invention in the liquid composition is not particularly limited, but is preferably 0.01 to 10% by weight, and more preferably 0.1 to 5% by weight.
• the thin film of the present invention contains the polymer compound of the present invention and is a luminescent thin film or a conductive thin film.
• the thin film of the present invention is prepared by spin coating, casting, micro gravure coating, gravure printing, bar coating, roll coating, wire bar coating, dip coating, spray coating, screen printing, flexographic printing. , Offset printing, ink jet, capillary coating, nozzle coating, and the like.
• the temperature is usually 100 ° C. or higher (eg, 130 ° C., 160 ° C.). It may be produced by baking.
• the light emission quantum yield of the thin film of the present invention is preferably 30% or more, more preferably 40% or more, still more preferably 50% or more, from the viewpoint of the luminance and light emission voltage of the device. Particularly preferred is 60% or more.
• the surface resistance of the thin film of the present invention is preferably 1 K ⁇ / ⁇ or less, more preferably 100 ⁇ / ⁇ or less, and even more preferably 10 ⁇ / ⁇ or less.
• the electrical conductivity can be increased by doping the thin film with a Lewis acid or an ionic compound.
• the element of the present invention contains the polymer compound of the present invention, and includes, for example, an electrode composed of an anode and a cathode, and an organic layer containing the polymer compound of the present invention provided between the electrodes. It is.
• the element of this invention is light emitting elements, such as an organic EL element, is demonstrated as the typical thing.
• the light emitting layer of the present invention is a single layer type light emitting device (anode / light emitting layer / cathode), the light emitting layer is composed of the thin film, and the light emitting layer contains the polymer compound of the present invention.
• the light emitting element of this invention is a multilayer type which has two or more layers between an anode and a cathode, those at least one layer consists of the said thin film. Examples of the layer structure of the multilayer light emitting device include the following (a) to (c).
• A Anode / hole injection layer (hole transport layer) / light emitting layer / cathode
• b anode / light emitting layer / electron injection layer (electron transport layer) / cathode
• c anode / hole injection layer (holes) (Transport layer) / light emitting layer / electron injection layer (electron transport layer) / cathode (where “/” indicates that the layers are laminated adjacently).
• the anode of the light emitting device of the present invention has a function of supplying holes to the hole injection layer, the hole transport layer, the light emitting layer, and the like. It is effective that the anode has a work function of 4.5 eV or more.
• the anode material can be a metal, an alloy, a metal oxide, an electrically conductive compound, or a mixture thereof.
• anode material examples include conductive metal oxides such as tin oxide, zinc oxide, indium oxide, and indium tin oxide (ITO); metals such as gold, silver, chromium, and nickel; the conductive metals A mixture or laminate of an oxide and a metal; an inorganic conductive material such as copper iodide and copper sulfide; an organic conductive material such as polyaniline, polythiophene (such as PEDOT), and polypyrrole; A laminate of two or more materials and ITO is exemplified.
• conductive metal oxides such as tin oxide, zinc oxide, indium oxide, and indium tin oxide (ITO)
• metals such as gold, silver, chromium, and nickel
• the conductive metals A mixture or laminate of an oxide and a metal
• an inorganic conductive material such as copper iodide and copper sulfide
• an organic conductive material such as polyaniline, polythiophene (such as PEDOT), and poly
• the cathode of the light emitting device of the present invention has a function of supplying electrons to the electron injection layer, the electron transport layer, the light emitting layer, and the like.
• a material for the cathode a metal, an alloy, a metal halide, a metal oxide, an electrically conductive compound, or a mixture thereof can be used.
• cathode materials include alkali metals (lithium, sodium, potassium, cesium, etc.) and their fluorides and oxides; alkaline earth metals (magnesium, calcium, barium, etc.) and their fluorides and oxides; gold, Metals such as silver, lead and aluminum; alloys and mixed metals (sodium-potassium alloy, sodium-potassium mixed metal, lithium-aluminum alloy, lithium-aluminum mixed metal, magnesium-silver alloy, magnesium-silver mixed metal, etc.) And rare earth metals (such as ytterbium) and indium.
• alkali metals lithium, sodium, potassium, cesium, etc.
• alkaline earth metals magnesium, calcium, barium, etc.
• gold Metals such as silver, lead and aluminum
• alloys and mixed metals sodium-potassium alloy, sodium-potassium mixed metal, lithium-aluminum alloy, lithium-aluminum mixed metal, magnesium-silver alloy, magnesium-silver mixed
• the hole injection layer and the hole transport layer of the light emitting device of the present invention have any one of the function of injecting holes from the anode, the function of transporting holes, and the function of blocking electrons injected from the cathode.
• a known material can be selected and used for the material of these layers. Examples of such materials include carbazole derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, styrylanthracene.
• Derivatives fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidin compounds, porphyrin compounds, polysilane compounds, poly (N-vinylcarbazole) derivatives, organic Examples thereof include silane derivatives and polymers containing these; conductive polymer oligomers such as aniline copolymers, thiophene oligomers, and polythiophene.
• the said material may be used individually by 1 type, or may use 2 or more types together.
• the hole injection layer and the hole transport layer may each independently have a single layer structure composed of one or more of the above materials, or a multilayer structure composed of a plurality of layers having the same composition or different compositions. There may be.
• the electron injection layer and the electron transport layer of the light emitting device of the present invention have any one of a function of injecting electrons from the cathode, a function of transporting electrons, and a function of blocking holes injected from the anode.
• a known material can be selected and used for the material of these layers. Examples of such materials include triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, fluorenone derivatives, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimide derivatives, fluorenylidenemethane.
• Derivatives distyrylpyrazine derivatives, aromatic tetracarboxylic anhydrides such as naphthalene and perylene, phthalocyanine derivatives, metal complexes (for example, metal complexes of 8-quinolinol derivatives, metal phthalocyanines, metal complexes having benzoxazole as a ligand) And metal complexes having benzothiazole as a ligand), and organosilane derivatives.
• the electron injection layer and the electron transport layer may each independently have a single layer structure composed of one or two or more of the above materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions. .
• an inorganic compound such as an insulator and a semiconductor may be used as a material for the electron injection layer and the electron transport layer. If the electron injection layer and the electron transport layer are made of an insulator or a semiconductor, current leakage can be effectively prevented and the electron injection property can be improved.
• the insulator include at least one metal compound selected from the group consisting of alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides, and alkaline earth metal halides.
• the alkali metal chalcogenide include CaO, BaO, SrO, BeO, BaS and CaSe.
• a reducing dopant may be added to the interface region between the cathode and the thin film in contact with the cathode.
• Reducing dopants include alkali metals, alkaline earth metal oxides, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal Preference is given to at least one compound selected from the group consisting of halides, rare earth metal oxides, rare earth metal halides, alkali metal complexes, alkaline earth metal complexes and rare earth metal complexes.
• the light emitting layer of the light emitting device of the present invention can inject holes from the anode, hole injection layer or hole transport layer when voltage is applied, and inject electrons from the cathode, electron injection layer or electron transport layer. Or the function of moving injected charges (electrons and holes) by the force of an electric field, and the function of providing a field for recombination of electrons and holes to connect to light emission.
• the light emitting layer of the light emitting device of the present invention preferably contains at least the polymer compound of the present invention.
• the polymer compound in the light emitting layer is usually 10% by weight to 100% by weight, preferably 50% by weight to 100% by weight, and preferably 80% by weight to 100% by weight with respect to the weight of the whole light emitting layer. It is more preferable that In the light emitting device of the present invention, the light emitting layer preferably contains the polymer compound of the present invention as a light emitting material.
• the method for forming each layer is not particularly limited, and a known method may be used. Examples of such methods include vacuum deposition methods (resistance heating deposition method, electron beam method, etc.), sputtering methods, LB methods, molecular lamination methods, coating methods (casting methods, spin coating methods, bar coating methods, blade coating methods, rolls). Coating method, gravure printing, screen printing, ink jet method and the like). Especially, since a manufacturing process can be simplified, it is preferable to form into a film by the apply
• a coating liquid can be prepared by dissolving the polymer compound of the present invention in a solvent, and the coating liquid can be formed on a desired layer (or electrode) by coating and drying.
• the coating solution may contain a resin as a binder, and the resin may be dissolved or dispersed in a solvent.
• a non-conjugated polymer for example, polyvinyl carbazole
• a conjugated polymer for example, a polyolefin-based polymer
• polyvinyl chloride polycarbonate, polystyrene, polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, poly (N-vinylcarbazole), hydrocarbon resin, ketone resin, phenoxy resin , Polyamide, ethyl cellulose, vinyl acetate, ABS resin, polyurethane, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, and silicone resin, and may be selected according to the purpose.
• the coating solution may contain optional components such as an antioxidant and a viscosity modifier depending on the purpose.
• each layer of the light emitting device of the present invention varies depending on the kind of material and the layer structure, but is usually 1 nm to 100 nm, preferably several nm to 1 ⁇ m.
• Examples of the use of the light emitting device of the present invention include a planar light source, an illumination light source (or light source), a sign light source, a backlight light source, a display device (display device), and a printer head.
• a configuration such as a segment type or a dot matrix type can be selected using a known driving technique, a driving circuit, or the like.
• the number average molecular weight and the weight average molecular weight were determined as a number average molecular weight and a weight average molecular weight in terms of polystyrene by size exclusion chromatography (SEC).
• SEC size exclusion chromatography
• GPC gel permeation chromatography
• [Analysis condition 1] The measurement sample was dissolved in tetrahydrofuran at a concentration of about 0.05% by weight. 30 ⁇ L of the obtained solution was injected into GPC (manufactured by Shimadzu Corporation, trade name: LC-10Avp). Tetrahydrofuran was used for the mobile phase of GPC, and flowed at a flow rate of 0.6 mL / min.
• the column was constructed by connecting two TSKgel SuperHM-H (Tosoh Corp.) and one TSKgel SuperH2000 (Tosoh Corp.) in series. A differential refractive index detector (manufactured by Shimadzu Corporation, trade name: RID-10A) was used as the detector.
• NMR measurement NMR measurement was performed under the following conditions.
• Apparatus Nuclear magnetic resonance apparatus, INOVA300 (trade name), manufactured by Varian Inc.
• Measurement solvent Deuterated chloroform Sample concentration: About 1% by weight Measurement temperature: 25 ° C
• HPLC high performance liquid chromatography
• Apparatus LC-20A (trade name), manufactured by Shimadzu Corporation
• Column Kaseisorb LC ODS-AM 4.6 mmI. D. ⁇ 100 mm, manufactured by Tokyo Chemical Industry
• Mobile phase 0.1 wt% acetic acid-containing water / 0.1 wt% acetic acid-containing acetonitrile
• Detector UV detector, detection wavelength 254 nm
• GC gas chromatography
• Device Agilent Technology 6890N Network GC Column: BPX5 0.25 mm I.D. D. ⁇ 30m, manufactured by SGE Analytical Science
• Mobile phase Helium Detector: Hydrogen flame ionization detector (FID)
• the emission spectrum peak of the luminescent organometallic complex compound was evaluated by the following method unless otherwise specified.
• the phosphorescent light-emitting compound was dissolved in xylene (manufactured by Kanto Chemical Co., Inc .: for electronics industry (EL grade)). At this time, the solution was prepared so that the concentration of the solid content would be 0.0008% by weight.
• This solution was excited with a wavelength of 350 nm using a fluorescence spectrophotometer (manufactured by JASCO Corporation, FP-6500), and the PL spectrum of the solution was measured to evaluate the emission spectrum peak.
• MALDI-TOFMS was measured under the following measurement conditions 1.
• Measurement condition 1 ⁇ -Cyano-4-hydroxycinnamic acid was dissolved in methanol to prepare a saturated solution, which was used as a matrix solution. 200 ⁇ L of chloroform was added to and dissolved in about 4 mg of the polymer compound to be measured, and 20 ⁇ L of the resulting solution was diluted with 200 ⁇ L of chloroform to obtain a sample solution. A matrix solution (20 ⁇ L) and a sample solution (20 ⁇ L) were mixed, applied to a MALDI plate, and MALDI-TOFMS was measured.
• the measurement was performed using a MALDI-TOFMS apparatus: Voyager-DE STR (manufactured by Applied Biosystems) in a measurement mode: Reflector, an acceleration voltage: 20 kV, and a laser: N 2 (337 nm).
• 1,4-dihexyl-2,5-dibromobenzene compound CM-1, 8.08 g, 20.0 mmol
• bis (pinacolato) diboron (12.19 g, 48.0 mmol) in a flask under an argon gas atmosphere
• potassium acetate 11.78 g, 120.0 mmol
• dehydrated 1,4-dioxane 100 ml
• the oil bath was removed, diluted with dehydrated tetrahydrofuran (400 ml), cooled in an ice bath, and then 2-isopropyloxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (148. 85 g, 800 mmol) was added.
• the ice bath was removed, and the mixture was heated in an oil bath at 80 ° C., and stirred for 1.5 hours under reflux. After removing the oil bath and further cooling in an ice bath, a saturated aqueous ammonium chloride solution (50 ml) was added and stirred for 30 minutes.
• the ice bath was removed, hexane (1500 ml) was added, and the mixture was vigorously stirred for 30 minutes.
• a silica gel layer was spread on a glass filter, and sodium sulfate was filtered through a THF solution and concentrated. Toluene was added to the obtained oil and heated to reflux. Next, after cooling to 70 ° C., isopropyl alcohol was added and stirred, and when it was allowed to stand at room temperature, crystals were formed. The crystals were filtered and dried, then charged into an eggplant flask, heated by adding hexane and activated carbon, and refluxed for 2 hours to obtain a mixture. Radiolite was laid on a glass filter, celite was laid thereon, and the mixture was heated to 70 ° C. in an oven, and the mixture was filtered using this.
• the Grignard reagent was added to a dehydrated tetrahydrofuran (100 ml) suspension of the needle crystals (12.0 g, compound CM-11) with stirring and heated to reflux. After cooling, the reaction solution was washed with dilute hydrochloric acid aqueous solution. The organic layer and the aqueous layer were separated, and the aqueous layer was extracted with diethyl ether. The obtained organic layers were combined and washed again with water. The organic layer was dehydrated with anhydrous magnesium sulfate, filtered, and concentrated. The obtained white solid was purified with a silica gel column and further recrystallized to obtain 6.5 g of Compound M-4 as a white solid.
• the Grignard reagent was added to a dehydrated tetrahydrofuran (100 ml) suspension of the needle crystals (12.0 g) with stirring, and the mixture was heated to reflux. After cooling, the reaction solution was washed with dilute hydrochloric acid aqueous solution. The organic layer and the aqueous layer were separated, and the aqueous layer was extracted with diethyl ether. The obtained organic layers were combined and washed again with water. The organic layer was dehydrated with anhydrous magnesium sulfate, filtered, and concentrated. The resulting white solid was purified with a silica gel column and recrystallized to obtain Compound M-5 (6.5 g) as a white solid.
• the reaction vessel was charged with compound CM-8 (1 equivalent) and dichloromethane (29 equivalents) to prepare a homogeneous solution and cooled to ⁇ 30 ° C.
• Boron trifluoride diethyl ether complex (BF 3 ⁇ OEt 2 , 1 equivalent) was added dropwise to the solution over 30 minutes. Then, it stirred at room temperature overnight.
• the reaction mixture was cooled to ⁇ 20 ° C., distilled water (112 equivalents) was added, and the mixture was stirred for 1 hour, and then allowed to stand and liquid separation was removed from the organic layer.
• the obtained powder was sufficiently dried with a vacuum dryer to obtain the target compound M-10 as a white powder (5 g, yield 50%).
• a light-emitting organometallic complex compound MC-1 represented by the formula:
• the emission spectrum peak of the luminescent organometallic complex compound MC-1 was 513 nm.
• t-Bu represents a tert-butyl group.
• the organic layer was recovered from the reaction solution and washed with 5 wt% aqueous sodium hydrogen carbonate solution and 10 wt% brine. The washed organic layer was dried over sodium sulfate and concentrated. The obtained concentrated liquid was purified by silica gel column chromatography (toluene), and the solvent was distilled off. The obtained residue was dissolved in chloroform and crystallized by adding ethanol. The crystals were collected by filtration and then washed with ethanol and dried to obtain Compound L-2 (169.2 g).
• the emission spectrum peak of the luminescent organometallic complex compound MC-2 was 611 nm.
• a metal complex complex 1 (6.94 g, 5.0 mmol), 5-bromo-2-phenylpyridine (7.32 g, 30.0 mmol) and diglyme (43 mL) were weighed into a reaction vessel, and trifluoromethanesulfonic acid was measured. Silver (2.57 g, 10.0 mmol) was added and stirred at 130 ° C. for 14 hours. The resulting reaction product was filtered off and the solid was dissolved in methylene chloride. The solution was filtered and the filtrate was concentrated. The precipitated solid was collected by filtration and washed with hexane to obtain a metal complex complex 2 (6.35 g, 7.1 mmol) represented by the above formula.
• a metal complex complex 3 (546 mg, 0.53 mmol), 2,4-di (4′-tert-butylphenyl) -6-chloro-1,3,5-triazine (702 mg, 1 .85 mmol), cesium carbonate (1.73 g, 5.31 mmol), tetrakis (triphenylphosphine) palladium (0) (196 mg, 0.17 mmol), and tetrahydrofuran (53 mL) were weighed and refluxed for 9 hours. The reaction solution was concentrated, and toluene was added to dissolve it.
• the resulting solution was purified by silica gel chromatography (developing solvent: chloroform / hexane mixed solvent). The eluted solution was recovered, the solvent was distilled off, and the residue was washed with methanol to obtain a metal complex complex4 (3.76 g, 2.0 mmol) represented by the above formula.
• the organic layer was washed with saturated brine and dried over sodium sulfate.
• the resulting solution was filtered and concentrated.
• the obtained concentrated liquid was purified by silica gel chromatography (developing solvent: toluene).
• the eluted solution was collected and the solvent was distilled off.
• the residue was dissolved by adding a chloroform / hexane mixed solvent.
• the resulting solution was purified by silica gel chromatography (developing solvent: chloroform / hexane), and the solvent was distilled off.
• the residue was dissolved in toluene, and acetonitrile was added to the resulting solution for purification by crystallization.
• the hole transporting polymer compound HP-1 was prepared by the following procedure. Under an inert gas atmosphere, Compound M-8 (17.3 g), Compound M-6 (10.4 g), 9,9-dioctyl-2,7-dibromofluorene (2.62 g), 9,9-bis ( Benzocyclobuten-4-yl) -2,7-dibromofluorene (1.51 g) and toluene (580 mL) were mixed and stirred while heating.
• the polymer compound HP-1 has the following constitutional units and molar ratios based on the charging ratio of raw material monomers, and is a high polymer in which (PA) constitutional units and constitutional units selected from (PB) are alternately polymerized. Presumed to be a molecular compound.
• the hole transporting polymer compound HP-2 was prepared by the following procedure. In an inert gas atmosphere, compound M-8 (0.9339 g), N, N′-bis (4-bromophenyl) -N, N′-bis (2,6-dimethyl-4-n-butylphenyl)- 1,4-phenylenediamine (1.9223 g), 9,9-dioctyl-2,7-dibromofluorene (0.5947 g), 9,9-bis (benzocyclobuten-4-yl) -2,7-dibromo Fluorene (0.3437 g) and toluene (118 mL) were mixed and stirred while heating.
• the hole transporting polymer compound HP-2 has the following structural units and molar ratios based on the monomer charge ratio, and the structural unit of (PA) and the structural unit selected from (PB) are alternately polymerized. It is estimated that the polymer compound. (In the formula, Me represents a methyl group, and n-Bu represents an n-butyl group.)
• Polymer compound A has the following repeating units and molar ratios based on the monomer charge ratio, and is estimated to be a polymer compound in which (PA) repeating units and repeating units selected from (PB) are alternately polymerized. Is done.
• a glass substrate having an ITO film with a thickness of 45 nm formed by sputtering is coated with an ethylene glycol monobutyl ether / water (3/2 (volume ratio)) solution of polythiophenesulfonic acid (Sigma Aldrich, trade name: Plexcore OC 1200).
• the film was spin-coated to form a film having a thickness of 65 nm and dried on a hot plate at 170 ° C. for 15 minutes.
• the hole transporting polymer compound HP-1 was spin-coated in a 0.7% by weight xylene solution to form a film having a thickness of about 20 nm. Then, it heated at 180 degreeC for 60 minutes on the hotplate.
• composition 1 was prepared by mixing so that the weight ratio was 70:30.
• the composition 1 was formed by spin coating at a rotational speed of 1800 rpm. The film thickness was about 80 nm. After drying this at 130 ° C. for 10 minutes under a nitrogen gas atmosphere, about 3 nm of sodium fluoride and then about 80 nm of aluminum were vapor-deposited as a cathode to produce an organic EL device. The metal deposition was started after the degree of vacuum reached 1 ⁇ 10 ⁇ 4 Pa or less.
• EL light emission electroluminescence light emission having a peak at 520 nm derived from the light-emitting organometallic complex compound MC-1 was obtained from this device.
• the device started to emit light at 3.0 V, showed light emission of 1000 cd / m 2 at 6.2 V, and had a maximum light emission efficiency of 60.88 cd / A.
• the organic EL element obtained above was driven at a constant current after setting the current value so that the initial luminance was 8000 cd / m 2, and the change in luminance with time was measured. As a result, the luminance was attenuated to 80% of the initial luminance after 72.1 hours, and was attenuated to 70% of the initial luminance after 235 hours.
• phenyl boric acid (0.20 g), palladium acetate (3.7 mg), tris (2-methoxyphenyl) phosphine (23.3 mg), and a 20 wt% tetraethylammonium hydroxide aqueous solution (58.3 g) were added. Heated to reflux for 15 hours.
• the organic layer was washed once with ion-exchanged water, twice with 10% by weight hydrochloric acid, twice with 3% by weight aqueous ammonia solution and twice with ion-exchanged water.
• Polymer compound B has the following repeating units and molar ratios based on the monomer charge ratio, and is estimated to be a polymer compound in which (PA) repeating units and repeating units selected from (PB) are alternately polymerized. Is done.
• Example 1 a solution of the polymer compound B dissolved in xylene solvent at a concentration of 1.9% by weight and dissolved in xylene solvent at a concentration of 1.9% by weight
• An organic EL device was produced in the same manner as in Example 1 except that the composition 2 was prepared by mixing the solution of the light-emitting organometallic complex compound MC-1 in a weight ratio of 70:30. did.
• the organic EL element obtained above was driven at a constant current after setting the current value so that the initial luminance was 8000 cd / m 2, and the change in luminance with time was measured. As a result, the luminance was attenuated to 80% of the initial luminance after 101.6 hours, and was attenuated to 70% of the initial luminance after 262.5 hours.
• phenylboric acid 0.059 g
• palladium acetate 1.7 mg
• tris (2-methoxyphenyl) phosphine 10.3 mg
• a 20 wt% tetraethylammonium hydroxide aqueous solution 17.1 g
• Example 1 ⁇ Production and Evaluation of Organic EL Device>
• a solution of the polymer compound C dissolved in a xylene solvent at a concentration of 1.9% by weight and a solution of the polymer compound C dissolved in a xylene solvent at a concentration of 1.9% by weight An organic EL device was produced in the same manner as in Example 1 except that the composition 3 was prepared by mixing the solution of the light-emitting organometallic complex compound MC-1 in a weight ratio of 70:30. did.
• EL light emission having a peak at 520 nm derived from the light-emitting organometallic complex compound MC-1 was obtained from this device.
• the device started to emit light from 2.9 V, showed light emission of 1000 cd / m 2 at 6.1 V, and had a maximum light emission efficiency of 61.8 cd / A.
• the organic EL element obtained above was driven at a constant current after setting the current value so that the initial luminance was 8000 cd / m 2, and the change in luminance with time was measured. As a result, the luminance was attenuated to 80% of the initial luminance after 44.4 hours, and was attenuated to 70% of the initial luminance after 163.5 hours.
• Polymer compound C has the following repeating units and molar ratios based on the monomer charge ratio, and is estimated to be a polymer compound in which (PA) repeating units and repeating units selected from (PB) are alternately polymerized. Is done.
• Polymer compound D has the following repeating units and molar ratios based on the monomer charge ratio, and is estimated to be a polymer compound in which (PA) repeating units and repeating units selected from (PB) are alternately polymerized. Is done.
• Example 1 ⁇ Production and Evaluation of Organic EL Device>
• a solution of the polymer compound D dissolved in a xylene solvent at a concentration of 1.5% by weight and a solution of the polymer compound D dissolved in a xylene solvent at a concentration of 1.5% by weight were used.
• An organic EL device was produced in the same manner as in Example 1 except that the composition 4 was prepared by mixing the solution of the light-emitting organometallic complex compound MC-1 in a weight ratio of 70:30. did.
• EL light emission having a peak at 520 nm derived from the light-emitting organometallic complex compound MC-1 was obtained from this device.
• the device started to emit light from 2.9 V, showed light emission of 1000 cd / m 2 at 6.0 V, and had a maximum light emission efficiency of 56.48 cd / A.
• the organic EL element obtained above was driven at a constant current after setting the current value so that the initial luminance was 8000 cd / m 2, and the change in luminance with time was measured. As a result, the luminance was attenuated to 80% of the initial luminance after 19.6 hours, and was attenuated to 70% of the initial luminance after 75.4 hours.
• phenylboric acid 0.078 g
• palladium acetate 2.1 mg
• tris (2-methoxyphenyl) phosphine 13.3 mg
• 20 wt% tetraethylammonium hydroxide aqueous solution 22.3 g
• Polymer compound E has the following repeating units and molar ratios based on the monomer charge ratio, and is estimated to be a polymer compound in which (PA) repeating units and repeating units selected from (PB) are alternately polymerized Is done.
• Example 1 a solution of the polymer compound E dissolved in xylene solvent at a concentration of 1.6% by weight and dissolved in xylene solvent at a concentration of 1.6% by weight
• An organic EL device was produced in the same manner as in Example 1 except that the composition 5 was prepared by mixing the solution of the light-emitting organometallic complex compound MC-1 in a weight ratio of 70:30. did.
• EL light emission having a peak at 520 nm derived from the light-emitting organometallic complex compound MC-1 was obtained from this device.
• the device started to emit light at 3.0 V, showed light emission of 1000 cd / m 2 at 6.7 V, and had a maximum light emission efficiency of 47.54 cd / A.
• the organic EL element obtained above was driven at a constant current after setting the current value so that the initial luminance was 8000 cd / m 2, and the change in luminance with time was measured. As a result, the luminance was attenuated to 80% of the initial luminance after 11.3 hours, and was attenuated to 70% of the initial luminance after 28.9 hours.
• Bistriphenylphosphine palladium dichloride (3.7 mg) was added and heated to 100 ° C., a 20 wt% tetraethylammonium hydroxide aqueous solution (18.5 g) was added dropwise, and the mixture was heated to reflux for 8 hours.
• phenylboric acid 0.065 g
• bistriphenylphosphine palladium dichloride 3. mg
• a 20 wt% tetraethylammonium hydroxide aqueous solution 18.5 g
• Polymer compound F has the following repeating units and molar ratios based on the monomer charge ratio, and is estimated to be a polymer compound in which (PA) repeating units and repeating units selected from (PB) are alternately polymerized. Is done.
• Me represents a methyl group
• t-Bu represents a tert-butyl group
• Example 1 the hole-transporting polymer compound HP-2 was spin-coated in a 0.7% by weight xylene solution to form a film having a thickness of about 20 nm.
• a solution of polymer compound F dissolved in xylene solvent at a concentration of 1.6 wt%, and a solution of luminescent organometallic complex compound MC-2 dissolved in xylene solvent at a concentration of 1.6 wt% Were mixed at a weight ratio of 92.5: 7.5, and the composition 6 was prepared, and the film thickness of the composition 6 was about 80 nm at a rotational speed of 1550 rpm by spin coating.
• An organic EL element was produced in the same manner as in Example 1 except that the film was formed so that
• EL light emission having a peak at 615 nm derived from the light-emitting organometallic complex compound MC-2 was obtained from this device.
• the device started to emit light at 2.3 V, showed light emission of 1000 cd / m 2 at 4.7 V, and had a maximum light emission efficiency of 21.15 cd / A.
• the organic EL element obtained above was driven at a constant current after setting the current value so that the initial luminance was 8000 cd / m 2, and the change in luminance with time was measured. As a result, the luminance was attenuated to 80% of the initial luminance after 525 hours, and was attenuated to 70% of the initial luminance after 1244.4 hours.
• Bistriphenylphosphine palladium dichloride (2.7 mg) was added, 20 wt% tetraethylammonium hydroxide aqueous solution (13.7 g) was added dropwise, and the mixture was heated to reflux for 7 hours.
• Polymer compound G has the following repeating units and molar ratios from the monomer charge ratio, and is estimated to be a polymer compound in which (PA) repeating units and repeating units selected from (PB) are alternately polymerized. Is done.
• Me represents a methyl group
• t-Bu represents a tert-butyl group
• Example 5 a solution of the polymer compound F dissolved at a concentration of 1.5% by weight and a luminescent organometallic dissolved in a xylene solvent at a concentration of 1.5% by weight
• An organic EL device was produced in the same manner as in Example 5 except that the composition 7 was prepared by mixing the solution of the complex compound MC-2 in a weight ratio of 92.5: 7.5. did.
• EL light emission having a peak at 615 nm derived from the light-emitting organometallic complex compound MC-2 was obtained from this device.
• the device started to emit light at 2.5 V, showed light emission of 1000 cd / m 2 at 5.0 V, and the maximum light emission efficiency was 16.93 cd / A.
• the organic EL element obtained above was driven at a constant current after setting the current value so that the initial luminance was 8000 cd / m 2, and the change in luminance with time was measured. As a result, the luminance attenuated to 80% of the initial luminance after 105 hours, and attenuated to 70% of the initial luminance after 408 hours.
• phenylboric acid 0.10 g
• bistriphenylphosphine palladium dichloride 3.5 mg
• toluene 50 mL
• polymer compound H a polymer compound (hereinafter referred to as “polymer compound H”).
• Polymer compound H has the following repeating units and molar ratios based on the monomer charge ratio, and is estimated to be a polymer compound in which (PA) repeating units and repeating units selected from (PB) are alternately polymerized. Is done.
• Me represents a methyl group
• t-Bu represents a tert-butyl group
• Example 5 In place of the composition 6, a solution of the polymer compound H dissolved in a xylene solvent at a concentration of 1.6% by weight and a solution of the polymer compound H dissolved in a xylene solvent at a concentration of 1.6% by weight. A solution of the luminescent organometallic complex compound MC-2 was mixed in a weight ratio of 92.5: 7.5 to prepare a composition 8, and an organic compound was prepared in the same manner as in Example 5. An EL element was produced.
• EL light emission having a peak at 615 nm derived from the light-emitting organometallic complex compound MC-2 was obtained from this device.
• the device started to emit light at 2.5 V, showed light emission of 1000 cd / m 2 at 5.5 V, and the maximum light emission efficiency was 18.20 cd / A.
• the organic EL element obtained above was driven at a constant current after setting the current value so that the initial luminance was 8000 cd / m 2, and the change in luminance with time was measured. As a result, the luminance attenuated to 80% of the initial luminance after 63 hours, and attenuated to 70% of the initial luminance after 148.2 hours.
• polymer compound I a polymer compound (hereinafter referred to as “polymer compound I”) was obtained.
• the polymer compound I had a polystyrene-equivalent number average molecular weight of 5.0 ⁇ 10 4 and a polystyrene-equivalent weight average molecular weight of 1.1 ⁇ 10 5 , measured based on Analysis Condition 2.
• the polymer compound I has the following formula: And a repeating unit represented by the following formula: (In the formula, Me represents a methyl group.) And a repeating unit represented by the following formula: And a repeating unit represented by the following formula: (In the formula, t-Bu represents a tert-butyl group.) Is a copolymer contained in a molar ratio of 40: 10: 40: 10.
• Example 1 ⁇ Production and Evaluation of Organic EL Device>
• a solution of the polymer compound I dissolved in a xylene solvent at a concentration of 2.2% by weight and a solution of the polymer compound I at a concentration of 2.2% by weight were dissolved in the xylene solvent.
• the composition 9 was prepared by mixing the light-emitting organometallic complex compound MC-1 with the solution in a weight ratio of 70:30, and the composition 9 was spin-coated at a rotational speed of 1600 rpm.
• An organic EL element was produced in the same manner as in Example 1 except that the film was formed in the same manner as in Example 1.
• EL light emission having a peak at 520 nm derived from the light-emitting organometallic complex compound MC-1 was obtained from this device.
• the device started to emit light at 2.64 V, showed light emission of 1000 cd / m 2 at 5.7 V, and had a maximum light emission efficiency of 62.80 cd / A.
• the organic EL element obtained above was driven at a constant current after setting the current value so that the initial luminance was 8000 cd / m 2, and the change in luminance with time was measured. As a result, the luminance was attenuated to 80% of the initial luminance after 82 hours.
• polymer compound J a polymer compound (hereinafter referred to as “polymer compound J”) was obtained.
• the polymer compound J had a polystyrene-equivalent number average molecular weight of 4.9 ⁇ 10 4 and a polystyrene-equivalent weight average molecular weight of 1.1 ⁇ 10 5 , measured based on Analysis Condition 2.
• the polymer compound J has the following formula: And a repeating unit represented by the following formula: (In the formula, Me represents a methyl group.) And a repeating unit represented by the following formula: And a repeating unit represented by the following formula: (In the formula, t-Bu represents a tert-butyl group.) Is a copolymer contained in a molar ratio of 40: 10: 40: 10.
• Example 1 ⁇ Production and Evaluation of Organic EL Device>
• a solution of the polymer compound J dissolved in a xylene solvent at a concentration of 2.2% by weight and a solution of the polymer compound J dissolved in a xylene solvent at a concentration of 2.2% by weight were used.
• the composition 10 was prepared by mixing a solution of the light-emitting organometallic complex compound MC-1 at a weight ratio of 70:30, and the composition 10 was spin-coated at a rotational speed of 1690 rpm.
• An organic EL element was produced in the same manner as in Example 1 except that the film was formed in the same manner as in Example 1.
• EL light emission having a peak at 520 nm derived from the light-emitting organometallic complex compound MC-1 was obtained from this device.
• the device started to emit light at 2.69 V, showed light emission of 1000 cd / m 2 at 5.4 V, and had a maximum light emission efficiency of 58.50 cd / A.
• the organic EL element obtained above was driven at a constant current after setting the current value so that the initial luminance was 8000 cd / m 2, and the change in luminance with time was measured. As a result, the luminance was attenuated to 80% of the initial luminance after 100 hours.
• Example 9 ⁇ Production and Evaluation of Organic EL Device>
• a solution of the polymer compound I dissolved in a xylene solvent at a concentration of 2.2% by weight and a solution of the polymer compound I at a concentration of 2.2% by weight were dissolved in the xylene solvent.
• the composition 11 was prepared by mixing the light-emitting organometallic complex compound MC-3 with a solution at a weight ratio of 70:30, and the composition 11 was spin-coated at a rotational speed of 1580 rpm.
• An organic EL element was produced in the same manner as in Example 7 except that the film was formed in the same manner as in Example 7.
• EL light emission having a peak at 605 nm derived from the luminescent organometallic complex compound MC-3 was obtained from this device.
• the device started to emit light at 2.74 V, showed light emission of 1000 cd / m 2 at 7.6 V, and had a maximum light emission efficiency of 27.80 cd / A.
• the organic EL element obtained above was driven at a constant current after setting the current value so that the initial luminance was 8000 cd / m 2, and the change in luminance with time was measured. As a result, the luminance was attenuated to 80% of the initial luminance after 41.9 hours.
• Example 10 ⁇ Production and Evaluation of Organic EL Device>
• a solution of the polymer compound J dissolved in a xylene solvent at a concentration of 2.2% by weight and a solution of the polymer compound J dissolved in a xylene solvent at a concentration of 2.2% by weight was prepared by mixing the light-emitting organometallic complex compound MC-3 with a solution at a weight ratio of 70:30, and the composition 12 was spin-coated at a rotation speed of 1620 rpm.
• An organic EL element was produced in the same manner as in Example 8 except that the film was formed in the same manner as in Example 8.
• EL light emission having a peak at 605 nm derived from the luminescent organometallic complex compound MC-3 was obtained from this device.
• the device started to emit light at 2.82 V, showed light emission of 1000 cd / m 2 at 7.7 V, and had a maximum light emission efficiency of 24.60 cd / A.
• the organic EL element obtained above was driven at a constant current after setting the current value so that the initial luminance was 8000 cd / m 2, and the change in luminance with time was measured. As a result, the luminance was attenuated to 80% of the initial luminance after 50.6 hours.
• Comparative Example 3 ⁇ Production and Evaluation of Organic EL Device>
• a solution of the polymer compound E dissolved in xylene solvent at a concentration of 2.2% by weight and dissolved in xylene solvent at a concentration of 2.2% by weight was mixed at a weight ratio of 70:30 to prepare a composition 13, and the composition 13 was spin-coated at a rotational speed of 2400 rpm.
• An organic EL element was produced in the same manner as in Comparative Example 1 except that the film was formed in the above step.
• the organic EL element obtained above was driven at a constant current after setting the current value so that the initial luminance was 8000 cd / m 2, and the change in luminance with time was measured. As a result, the luminance was attenuated to 80% of the initial luminance after 5.3 hours.
• Example 11 ⁇ Production and Evaluation of Organic EL Device>
• a solution of the polymer compound F dissolved in xylene solvent at a concentration of 1.8% by weight and dissolved in xylene solvent at a concentration of 1.8% by weight was mixed at a weight ratio of 92.5: 7.5 to prepare a composition 14, and the composition 14 was spin-coated.
• An organic EL device was produced in the same manner as in Example 5 except that the film was formed at a rotational speed of 2540 rpm.
• EL light emission having a peak at 625 nm derived from the light-emitting organometallic complex compound MC-4 was obtained from this device.
• the device started light emission from 2.41 V, showed light emission of 1000 cd / m 2 at 4.5 V, and the maximum light emission efficiency was 11.70 cd / A.
• the organic EL element obtained above was driven at a constant current after setting the current value so that the initial luminance was 8000 cd / m 2, and the change in luminance with time was measured. As a result, the luminance was attenuated to 80% of the initial luminance after 107.2 hours. This was 6.7 times longer than that of Comparative Example 4.
• Example 12 ⁇ Production and Evaluation of Organic EL Device>
• a solution of the polymer compound F dissolved in xylene solvent at a concentration of 1.8% by weight and dissolved in xylene solvent at a concentration of 1.8% by weight was prepared by mixing the light-emitting organometallic complex compound MC-3 with a solution in a weight ratio of 92.5: 7.5, and the composition 15 was spin-coated.
• An organic EL device was produced in the same manner as in Example 5 except that the film was formed at a rotational speed of 2570 rpm.
• EL light emission having a peak at 600 nm derived from the light-emitting organometallic complex compound MC-3 was obtained from this device.
• the device started to emit light at 2.29 V, emitted 1000 cd / m 2 at 4.2 V, and had a maximum luminous efficiency of 31.20 cd / A.
• the organic EL element obtained above was driven at a constant current after setting the current value so that the initial luminance was 8000 cd / m 2, and the change in luminance with time was measured. As a result, the luminance was attenuated to 80% of the initial luminance after 593.8 hours. This was 5.76 times longer than that of Comparative Example 5.
• Example 13 ⁇ Production and Evaluation of Organic EL Device>
• a solution of the polymer compound F dissolved in xylene solvent at a concentration of 1.8% by weight and dissolved in xylene solvent at a concentration of 1.8% by weight was prepared by mixing the light-emitting organometallic complex compound MC-5 with a solution at a weight ratio of 92.5: 7.5, and the composition 16 was spin-coated.
• An organic EL device was produced in the same manner as in Example 5 except that the film was formed at a rotational speed of 2740 rpm.
• EL light emission having a peak at 615 nm derived from the light-emitting organometallic complex compound MC-5 was obtained from this device.
• the device started to emit light at 2.39 V, showed light emission of 1000 cd / m 2 at 5.0 V, and had a maximum light emission efficiency of 20.40 cd / A.
• the organic EL element obtained above was driven at a constant current after setting the current value so that the initial luminance was 8000 cd / m 2, and the change in luminance with time was measured. As a result, the luminance was attenuated to 80% of the initial luminance after 493.6 hours. This was 8.9 times longer than that of Comparative Example 6.
• Bis (triphenylphosphine) palladium dichloride (3.70 mg) was added to the mixture and heated to 100 ° C., and a 20 wt% tetraethylammonium hydroxide aqueous solution (18.5 g) was added dropwise and heated to reflux.
• phenylboric acid (0.0650 g) bis (triphenylphosphine) palladium dichloride (3.70 mg) and a 20 wt% tetraethylammonium hydroxide aqueous solution (18.5 g) were added, and the mixture was heated to reflux overnight.
• polymer compound K a polymer compound (hereinafter referred to as “polymer compound K”).
• Polymer compound K has the following constitutional units and molar ratios from the monomer charge ratio, and is presumed to be a polymer compound in which constitutional units of (PA) and constitutional units selected from (PB) are alternately polymerized. Is done. (In the formula, Me represents a methyl group, and n-Bu represents an n-butyl group.)
• Example 5 a solution of the polymer compound K dissolved in a xylene solvent at a concentration of 1.8% by weight and a solution of the polymer compound K at a concentration of 1.8% by weight were dissolved in the xylene solvent.
• the composition 17 was prepared by mixing the light-emitting organometallic complex compound MC-4 with a solution at a weight ratio of 92.5: 7.5, and the composition 17 was spin-coated.
• An organic EL device was produced in the same manner as in Example 5 except that the film was formed at a rotational speed of 2000 rpm.
• EL light emission having a peak at 625 nm derived from the light-emitting organometallic complex compound MC-4 was obtained from this device.
• the device started to emit light at 2.34 V, showed light emission of 1000 cd / m 2 at 4.2 V, and the maximum light emission efficiency was 11.40 cd / A.
• the organic EL element obtained above was driven at a constant current after setting the current value so that the initial luminance was 8000 cd / m 2, and the change in luminance with time was measured. As a result, the luminance was attenuated to 80% of the initial luminance after 71.1 hours. This was 4.44 times longer than that of Comparative Example 4.
• Example 15 ⁇ Production and Evaluation of Organic EL Device>
• a solution of the polymer compound K dissolved in a xylene solvent at a concentration of 1.8% by weight and a solution of the polymer compound K at a concentration of 1.8% by weight were dissolved in the xylene solvent.
• the composition 18 was prepared by mixing the light-emitting organometallic complex compound MC-3 with a solution at a weight ratio of 92.5: 7.5, and the composition 18 was spin-coated.
• An organic EL device was produced in the same manner as in Example 5 except that the film was formed at a rotational speed of 2120 rpm.
• EL light emission having a peak at 600 nm derived from the light-emitting organometallic complex compound MC-3 was obtained from this device.
• the device started to emit light at 2.26 V, showed light emission of 1000 cd / m 2 at 3.9 V, and the maximum light emission efficiency was 30.90 cd / A.
• the organic EL element obtained above was driven at a constant current after setting the current value so that the initial luminance was 8000 cd / m 2, and the change in luminance with time was measured. As a result, the luminance was attenuated to 80% of the initial luminance after 360.2 hours. This was 3.49 times longer than that of Comparative Example 5.
• Example 16 ⁇ Production and Evaluation of Organic EL Device>
• a solution of the polymer compound K dissolved in a xylene solvent at a concentration of 1.8% by weight and a solution of the polymer compound K at a concentration of 1.8% by weight were dissolved in the xylene solvent.
• the composition 19 was prepared by mixing the light-emitting organometallic complex compound MC-5 with a solution at a weight ratio of 92.5: 7.5, and the composition 19 was spin-coated.
• An organic EL device was produced in the same manner as in Example 5 except that the film was formed at a rotation speed of 2090 rpm.
• the organic EL element obtained above was driven at a constant current after setting the current value so that the initial luminance was 8000 cd / m 2, and the change in luminance with time was measured. As a result, the luminance was attenuated to 80% of the initial luminance after 297.1 hours. This was 5.35 times longer than that of Comparative Example 6.
• Bis (triphenylphosphine) palladium dichloride (1.0 mg) was added to the mixture and heated to 100 ° C., 20 wt% tetraethylammonium hydroxide aqueous solution (7.64 g) was added dropwise, and the mixture was heated to reflux for 5 hours.
• phenylboric acid 0.035 g
• bis (triphenylphosphine) palladium dichloride 1.0 mg
• a 20 wt% tetraethylammonium hydroxide aqueous solution 7.64 g
• polymer compound L a polymer compound
• Polymer compound L has the following structural units and molar ratios from the monomer charge ratio, and is a polymer compound in which structural units of (PA) and structural units selected from (PB) are alternately polymerized: Presumed. (In the formula, Me represents a methyl group, and t-Bu represents a tert-butyl group.)
• Example 5 a solution of the polymer compound L dissolved in a xylene solvent at a concentration of 2.0% by weight and a solution of the polymer compound L at a concentration of 2.0% by weight were dissolved in the xylene solvent.
• the composition 20 was prepared by mixing the light-emitting organometallic complex compound MC-2 with a solution at a weight ratio of 92.5: 7.5, and the composition 20 was spin-coated.
• An organic EL device was produced in the same manner as in Example 5 except that the film was formed at a rotational speed of 3500 rpm.
• EL light emission having a peak at 615 nm derived from the light-emitting organometallic complex compound MC-2 was obtained from this device.
• the device started to emit light at 2.28 V, showed light emission of 1000 cd / m 2 at 4.4 V, and had a maximum light emission efficiency of 18.20 cd / A.
• the organic EL element obtained above was driven at a constant current after setting the current value so that the initial luminance was 8000 cd / m 2, and the change in luminance with time was measured. As a result, the luminance was attenuated to 80% of the initial luminance after 238.2 hours. This was 3.78 times longer than that of Comparative Example 2.
• Example 18 ⁇ Production and Evaluation of Organic EL Device>
• a solution of the polymer compound L dissolved in a xylene solvent at a concentration of 2.0% by weight and a solution of the polymer compound L at a concentration of 2.0% by weight were dissolved in the xylene solvent.
• the composition 21 was prepared by mixing the light-emitting organometallic complex compound MC-3 with a solution at a weight ratio of 92.5: 7.5, and the composition 21 was spin-coated.
• An organic EL device was produced in the same manner as in Example 5 except that the film was formed at a rotational speed of 3000 rpm.
• the organic EL element obtained above was driven at a constant current after setting the current value so that the initial luminance was 8000 cd / m 2, and the change in luminance with time was measured. As a result, the luminance was attenuated to 80% of the initial luminance after 517.3 hours. This was 5.02 times longer than that of Comparative Example 5.
• Example 19 ⁇ Production and Evaluation of Organic EL Device>
• the composition 22 was prepared by mixing the light-emitting organometallic complex compound MC-4 with a solution at a weight ratio of 92.5: 7.5, and the composition 22 was spin-coated.
• An organic EL device was produced in the same manner as in Example 5 except that the film was formed at a rotational speed of 2500 rpm.
• EL light emission having a peak at 625 nm derived from the light-emitting organometallic complex compound MC-4 was obtained from this device.
• the device started to emit light at 2.41 V, showed light emission of 1000 cd / m 2 at 4.6 V, and the maximum light emission efficiency was 11.40 cd / A.
• the organic EL element obtained above was driven at a constant current after setting the current value so that the initial luminance was 8000 cd / m 2, and the change in luminance with time was measured. As a result, the luminance was attenuated to 80% of the initial luminance after 86.1 hours. This was 5.38 times longer than that of Comparative Example 4.
• Example 20 ⁇ Production and Evaluation of Organic EL Device>
• a solution of the polymer compound G dissolved in xylene solvent at a concentration of 1.8% by weight and dissolved in xylene solvent at a concentration of 1.8% by weight was prepared by mixing the light-emitting organometallic complex compound MC-3 with a solution at a weight ratio of 92.5: 7.5, and the composition 23 was spin-coated.
• An organic EL element was produced in the same manner as in Example 5 except that the film was formed at a rotational speed of 2370 rpm.
• EL light emission having a peak at 600 nm derived from the light-emitting organometallic complex compound MC-3 was obtained from this device.
• the device started to emit light at 2.31 V, emitted 1000 cd / m 2 at 4.3 V, and had a maximum luminous efficiency of 31.80 cd / A.
• the organic EL element obtained above was driven at a constant current after setting the current value so that the initial luminance was 8000 cd / m 2, and the change in luminance with time was measured. As a result, the luminance was attenuated to 80% of the initial luminance after 308.1 hours. This was 2.99 times longer than that of Comparative Example 5.
• Example 21 ⁇ Production and Evaluation of Organic EL Device>
• a solution of the polymer compound G dissolved in xylene solvent at a concentration of 1.8% by weight and dissolved in xylene solvent at a concentration of 1.8% by weight was prepared by mixing the light-emitting organometallic complex compound MC-5 with a solution at a weight ratio of 92.5: 7.5, and the composition 24 was spin-coated.
• An organic EL device was produced in the same manner as in Example 5 except that the film was formed at a rotational speed of 2500 rpm.
• EL light emission having a peak at 615 nm derived from the light-emitting organometallic complex compound MC-5 was obtained from this device.
• the device started to emit light at 2.39 V, showed light emission of 1000 cd / m 2 at 5.0 V, and had a maximum light emission efficiency of 20.40 cd / A.
• the organic EL element obtained above was driven at a constant current after setting the current value so that the initial luminance was 8000 cd / m 2, and the change in luminance with time was measured. As a result, the luminance attenuated to 80% of the initial luminance after 443.4 hours. This was 7.99 times longer than that of Comparative Example 6.
• Example 5 ⁇ Production and Evaluation of Organic EL Device>
• a solution of the polymer compound H dissolved in a xylene solvent at a concentration of 1.4% by weight and a solution of the polymer compound H in a concentration of 1.4% by weight were dissolved in the xylene solvent.
• the composition 25 was prepared by mixing the light-emitting organometallic complex compound MC-4 with a solution at a weight ratio of 92.5: 7.5, and the composition 25 was spin-coated.
• An organic EL device was produced in the same manner as in Example 5 except that the film was formed at a rotational speed of 2000 rpm.
• EL light emission having a peak at 625 nm derived from the light-emitting organometallic complex compound MC-4 was obtained from this device.
• the device started to emit light at 2.59 V, showed light emission of 1000 cd / m 2 at 5.1 V, and the maximum light emission efficiency was 10.80 cd / A.
• the organic EL element obtained above was driven at a constant current after setting the current value so that the initial luminance was 8000 cd / m 2, and the change in luminance with time was measured. As a result, the luminance was attenuated to 80% of the initial luminance after 16.0 hours.
• Example 5 ⁇ Production and Evaluation of Organic EL Device>
• a solution of the polymer compound H dissolved in a xylene solvent at a concentration of 1.5% by weight and a solution of the polymer compound H dissolved in a xylene solvent at a concentration of 1.5% by weight were used.
• the composition 26 was prepared by mixing a solution of the light-emitting organometallic complex compound MC-3 with a weight ratio of 92.5: 7.5, and the composition 26 was spin-coated.
• An organic EL device was produced in the same manner as in Example 5 except that the film was formed at a rotation speed of 2950 rpm.
• EL light emission having a peak at 600 nm derived from the light-emitting organometallic complex compound MC-3 was obtained from this device.
• the device started to emit light at 2.46 V, showed light emission of 1000 cd / m 2 at 4.5 V, and had a maximum light emission efficiency of 29.10 cd / A.
• the organic EL element obtained above was driven at a constant current after setting the current value so that the initial luminance was 8000 cd / m 2, and the change in luminance with time was measured. As a result, the luminance was attenuated to 80% of the initial luminance after 103.1 hours.
• Example 6 ⁇ Production and Evaluation of Organic EL Device>
• a solution of the polymer compound H dissolved in a xylene solvent at a concentration of 1.4% by weight and a solution of the polymer compound H in a concentration of 1.4% by weight were dissolved in the xylene solvent.
• the composition 27 was prepared by mixing the light-emitting organometallic complex compound MC-5 with a solution at a weight ratio of 92.5: 7.5, and the composition 27 was spin-coated.
• An organic EL device was produced in the same manner as in Example 5 except that the film was formed at a rotational speed of 2110 rpm.
• the organic EL element obtained above was driven at a constant current after setting the current value so that the initial luminance was 8000 cd / m 2, and the change in luminance with time was measured. As a result, the luminance was attenuated to 80% of the initial luminance after 55.5 hours.
• reaction solution was transferred to a separatory funnel, washed with 0.5 mol / L hydrochloric acid and 10% by weight saline, the organic layer was dehydrated with magnesium sulfate, and then passed through a funnel filled with silica gel. Is distilled off under reduced pressure. The obtained residue is recrystallized in a chloroform-methanol system to obtain white compound CM-16.
• Me represents a methyl group
• t-Bu represents a tert-butyl group
• antimony pentachloride (15 g, 50 mmol) is slowly added dropwise, and after completion of the addition, the temperature is raised to room temperature, followed by stirring for 48 hours or more.
• the resulting reaction mixture is added dropwise to a 25 wt% aqueous ammonia solution with stirring. If precipitation occurs in the organic layer or an emulsion is formed, dilute with chloroform.
• the aqueous layer is removed from the reaction solution, and the organic layer is washed twice or more with ion-exchanged water and dehydrated with sodium sulfate.
• the solvent is distilled off under reduced pressure, the resulting residue is dissolved in chloroform, passed through a funnel filled with silica gel, and the solvent is distilled off under reduced pressure.
• the obtained residue is recrystallized in a chloroform-methanol system to obtain white compound M-11.

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• 2011
  • 2011-07-14 WO PCT/JP2011/066161 patent/WO2012008550A1/ja active Application Filing
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