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Definitions

• the present invention relates to an amine polymer compound and a light emitting device using the same.
• Polymer compounds having a fluorene structure such as 9,9-dialkylfluorene in which two alkyl groups are introduced at the 9-position of the fluorene structure are known to be useful for the production of light-emitting elements (polymer LEDs, etc.).
• a polymer compound having excellent luminous efficiency a polymer compound in which two triphenylamine skeletons are introduced at the 9-position of the fluorene structure (Japanese Patent Publication No. 2004-500143), and two different aryl groups are located at the 9-position of the fluorene structure.
• a single polymer compound Japanese Patent Publication No. 2002-527553 is known.
• a light-emitting element including these polymer compounds is an index of external quantum yield (luminous efficiency in consideration of chromaticity) at a luminance of 1000 cd / m 2 which is a practical area when used for a display or the like. ) Is not always enough.
• An object of the present invention is to provide a polymer compound useful for manufacturing a light-emitting element having an excellent external quantum yield at a luminance of 1000 cd / m 2 .
• the present invention first provides a polymer compound containing a structural unit represented by the following formula (1a). [In formula, A ring and B ring represent the aromatic-hydrocarbon ring which may have a substituent each independently. R 1 is a group represented by the following formula (2).
• R 2 represents an aryl group or a monovalent aromatic heterocyclic group, and the hydrogen atom in these groups is an alkyl group, alkoxy group, alkylthio group, substituted carbonyl group, substituted carboxyl group, aryl group, aryloxy group, arylthio group.
• Ar 1 represents an arylene group or a divalent group in which two or more identical or different arylene groups are directly connected.
• Ar 4 and Ar 5 each independently represents an aryl group or a monovalent aromatic heterocyclic group.
• Ar 2 and Ar 3 each independently represent an arylene group or a divalent aromatic heterocyclic group.
• Ar 2 and Ar 3 are phenylene groups
• R 6 represents a hydrogen atom, an alkyl group, an aryl group, or a monovalent aromatic heterocyclic group.
• the hydrogen atoms in the groups represented by Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 and R 6 are an alkyl group, an alkoxy group, an alkylthio group, a substituted carbonyl group, a substituted carboxyl group, an aryl group, and an aryl group, respectively. It may be substituted with an oxy group, an arylthio group, an aralkyl group, a monovalent aromatic heterocyclic group, a fluorine atom or a cyano group.
• a plurality of R 6 When a plurality of R 6 are present, they may be the same or different.
• the present invention provides a compound represented by the following formula (A).
• R 1 , R 2 , R 3a , R 4a , R 5a , R 3b , R 4b and R 5b have the same meaning as described above.
• R 20 represents an alkyl group or an aryl group which may be substituted with an alkyl group, an alkoxy group, a nitro group, a fluorine atom or a cyano group.
• R 21 and R 22 each independently represents a hydrogen atom or an alkyl group. Two R 21 s may be the same or different, and may together form a ring. Three R 22 s may be the same or different and may form a ring together.
• Q 1 represents a monovalent cation of lithium, sodium, potassium, rubidium or cesium.
• Y 1 represents a bromine atom, an iodine atom or a chlorine atom.
• the present invention provides a composition and a thin film containing the polymer compound.
• the present invention provides a solution containing the polymer compound and a solvent.
• the present invention provides a light emitting device having an electrode composed of an anode and a cathode, and an organic layer containing the polymer compound provided between the electrodes.
• the present invention provides a planar light source and a display device provided with the light emitting element.
• structural unit means one or more units present in a polymer compound, but the structural unit is “repeating unit” (that is, two or more units exist in a polymer compound).
• the unit is preferably contained in the polymer compound.
• the “n-valent aromatic heterocyclic group” (n is 1 or 2) means an atomic group obtained by removing n hydrogen atoms from an aromatic heterocyclic compound, and has a condensed ring. Also includes groups.
• Heterocyclic compound is an organic compound having a cyclic structure in which the atoms constituting the ring are not only carbon atoms, but also oxygen atoms, sulfur atoms, nitrogen atoms, phosphorus atoms, boron atoms, silicon atoms, etc. The compound containing the hetero atom of these.
• Aromatic heterocyclic compound '' means oxadiazole, thiadiazole, thiazole, oxazole, thiophene, pyrrole, phosphole, furan, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole, dibenzosilol, dibenzophos
• a heterocyclic compound containing a heteroatom such as a hole, wherein the heterocyclic ring itself shows aromaticity; a heterocycle containing a heteroatom such as phenoxazine, phenothiazine, dibenzoborol, dibenzosilol, benzopyran itself Even if it does not show aromaticity, it means a compound in which an aromatic ring is condensed to the heterocyclic ring.
• the high molecular compound of this invention contains the structural unit represented by Formula (1a).
• the aromatic hydrocarbon ring represented by the A ring and the B ring usually has 6 to 14 carbon atoms constituting the aromatic ring.
• the aromatic hydrocarbon ring include a benzene ring, a naphthalene ring, a fluorene ring, an anthracene ring, and a phenanthrene ring.
• the aromatic hydrocarbon ring may have a substituent.
• a bond exists on each of the A ring and the B ring.
• R 2 Is an atomic group obtained by removing one hydrogen atom from an aromatic hydrocarbon, and includes a group having a condensed ring.
• the aryl group usually has 6 to 60 carbon atoms, preferably 6 to 48 carbon atoms, more preferably 6 to 20 carbon atoms, and still more preferably 6 to 14 carbon atoms.
• the carbon number does not include the carbon number of the substituent.
• aryl group a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthracenyl group, a 2-anthracenyl group, a 9-anthracenyl group, a 1-tetracenyl group, a 2-tetracenyl group, a 5-tetracenyl group, 1- Pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-perylenyl group, 3-perylenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 1-biphenylenyl group, 2-biphenylenyl group, 2- Examples thereof include a phenanthrenyl group, a 9-phenanthrenyl group, a 6-chrycenyl group, and a 1-coronenyl group.
• the hydrogen atom in the aryl group is alkyl group, alkoxy group, alkylthio group, substituted carbonyl group, substituted carboxyl group, aryl group, aryloxy group, arylthio group, aralkyl group, monovalent aromatic heterocyclic group, fluorine atom, cyano It may be substituted with a group.
• R 2 The monovalent aromatic heterocyclic group represented by general formula (C) has usually 3 to 60 carbon atoms, preferably 3 to 20 carbon atoms. The carbon number does not include the carbon number of the substituent.
• Examples of the monovalent aromatic heterocyclic group include 2-oxadiazole group, 2-thiadiazole group, 2-thiazole group, 2-oxazole group, 2-thienyl group, 2-pyrrolyl group, 2-furyl group, 2- Pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-pyrazyl group, 2-pyrimidyl group, 2-triazyl group, 3-pyridazyl group, quinolyl group, isoquinolyl group, 2-carbazolyl group, 3-carbazolyl group, 2 -Phenoxazinyl group, 3-phenoxazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group, etc. are mentioned.
• the hydrogen atom in the monovalent aromatic heterocyclic group is an alkyl group, an alkoxy group, an alkylthio group, a substituted carbonyl group, a substituted carboxyl group, an aryl group, an aryloxy group, an arylthio group, an aralkyl group, or a monovalent aromatic heterocyclic ring.
• the alkyl group may be linear, branched or cyclic, and usually has 1 to 20 carbon atoms.
• alkyl group examples include methyl group, ethyl group, propyl group, i-propyl group, butyl group, i-butyl group, t-butyl group, pentyl group, isoamyl group, hexyl group, cyclohexyl group, heptyl group, octyl group, Examples include 2-ethylhexyl group, nonyl group, decyl group, 3,7-dimethyloctyl group, dodecyl group, trifluoromethyl group, pentafluoroethyl group, perfluorobutyl group, perfluorohexyl group, perfluorooctyl group and the like.
• the alkoxy group may be linear, branched or cyclic, and usually has 1 to 20 carbon atoms.
• Examples of the alkoxy group include methoxy group, ethoxy group, propyloxy group, i-propyloxy group, butoxy group, i-butoxy group, t-butoxy group, pentyloxy group, hexyloxy group, cyclohexyloxy group, heptyloxy group, Octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, 3,7-dimethyloctyloxy group, dodecyloxy group, trifluoromethoxy group, pentafluoroethoxy group, perfluorobutoxy group, perfluorohexyloxy group, A perfluorooctyloxy group, a methoxymethyloxy group, a 2-methoxyethyloxy group, a 2-ethoxyethyloxy group,
• the alkylthio group may be linear, branched or cyclic, and usually has 1 to 20 carbon atoms.
• Examples of the alkylthio group include a butylthio group, a hexylthio group, an octylthio group, a 2-ethylhexylthio group, a 3,7-dimethyloctylthio group, and a dodecylthio group.
• the substituted carbonyl group usually has 2 to 60 carbon atoms.
• substituted carbonyl group examples include an alkyl group, an aryl group, an aralkyl group, or a carbonyl group substituted with a monovalent aromatic heterocyclic group, and an acetyl group, a butyryl group, and a benzoyl group are preferable.
• the substituted carboxyl group usually has 2 to 60 carbon atoms.
• Examples of the substituted carboxyl group include an alkyl group, an aryl group, an aralkyl group or a carboxyl group substituted with a monovalent aromatic heterocyclic group, a methoxycarbonyl group, an ethoxycarbonyl group, a butoxycarbonyl group, a phenoxycarbonyl group, A benzyloxycarbonyl group is preferred.
• the aryl group is R 2 This is the same as explained and exemplified in the section of the aryl group represented by The aryloxy group usually has 6 to 60 carbon atoms.
• aryloxy group a phenoxy group, C 1 ⁇ C 12 Alkoxyphenoxy group (“C 1 ⁇ C 12 “Alkoxy” means that the alkoxy moiety has 1 to 12 carbon atoms, and the same shall apply hereinafter), C 1 ⁇ C 12 Alkylphenoxy group (“C 1 ⁇ C 12 “Alkyl” means that the alkyl moiety has 1 to 12 carbon atoms, and the same shall apply hereinafter), 1-naphthyloxy group, 2-naphthyloxy group, pentafluorophenyloxy group and the like.
• the arylthio group usually has 6 to 60 carbon atoms.
• arylthio group a phenylthio group, C 1 ⁇ C 12 Alkoxyphenylthio group, C 1 ⁇ C 12 Examples thereof include an alkylphenylthio group, a 1-naphthylthio group, a 2-naphthylthio group, and a pentafluorophenylthio group.
• the aralkyl group usually has 7 to 60 carbon atoms.
• phenyl-C 1 ⁇ C 12 Alkyl group As an aralkyl group, phenyl-C 1 ⁇ C 12 Alkyl group, C 1 ⁇ C 12 Alkoxyphenyl-C 1 ⁇ C 12 Alkyl group, C 1 ⁇ C 12 Alkylphenyl-C 1 ⁇ C 12 Alkyl group, 1-naphthyl-C 1 ⁇ C 12 Alkyl group, 2-naphthyl-C 1 ⁇ C 12 An alkyl group etc. are mentioned.
• the monovalent aromatic heterocyclic group as a substituent is R 2 This is the same as explained and exemplified in the section of monovalent aromatic heterocyclic group as the group represented by formula (1).
• R 2 Is preferably an aryl group, and is substituted with an alkyl group, an alkoxy group or an aryl group from the viewpoint of the balance between the solubility of the polymer compound of the present invention in an organic solvent and the heat resistance.
• An aryl group and an unsubstituted aryl group are more preferred, an aryl group substituted with an alkyl group or an aryl group and an unsubstituted aryl group are more preferred, and an aryl group substituted with an alkyl group is particularly preferred.
• R 2 As preferable examples of the group represented by formula (I), phenyl group, 4-tolyl group, 4-butylphenyl group, 4-t-butylphenyl group, 4-hexylphenyl group, 4-octylphenyl group, 4- (2 -Ethylhexyl) phenyl group, 4- (3,7-dimethyloctyl) phenyl group, 3-tolyl group, 3-butylphenyl group, 3-t-butylphenyl group, 3-hexylphenyl group, 3-octylphenyl group, 3- (2-ethylhexyl) phenyl group, 3- (3,7-dimethyloctyl) phenyl group, 3,5-dimethylphenyl group, 3,5-di- (t-butyl) phenyl group, 3,4-dihexyl Phenyl group, 3,4-dioctylphenyl group, 1-nap
• R 1 The group represented by the formula (2) represented by In formula (2), Ar 1 , Ar 2 And Ar 3
• the arylene group represented by the formula means an atomic group obtained by removing two hydrogen atoms from an aromatic hydrocarbon, and includes a group having a condensed ring.
• the arylene group usually has 6 to 60 carbon atoms. The carbon number does not include the carbon number of the substituent.
• Arylene groups include 1,4-phenylene groups, 1,3-phenylene groups, 1,2-phenylene groups and the like; naphthalene-1,4-diyl groups, naphthalene-1,5-diyl groups, naphthalene- Naphthalenediyl group such as 2,6-diyl group; anthracene such as anthracene-1,4-diyl group, anthracene-1,5-diyl group, anthracene-2,6-diyl group, anthracene-9,10-diyl group Diyl group; phenanthrene diyl group such as phenanthrene-2,7-diyl group; naphthacene diyl group such as naphthacene-1,7-diyl group and naphthacene-2,8-diyl group; fluorene-2,7-diyl group, 7H- Such as benzo [c] fluoren
• the hydrogen atom in the arylene group is alkyl group, alkoxy group, alkylthio group, substituted carbonyl group, substituted carboxyl group, aryl group, aryloxy group, arylthio group, aralkyl group, monovalent aromatic heterocyclic group, fluorine atom, cyano It may be substituted with a group or the like.
• Ar 2 And Ar 3 In general, the divalent aromatic heterocyclic group represented by the formula has 2 to 60 carbon atoms. The carbon number does not include the carbon number of the substituent.
• divalent aromatic heterocyclic group examples include 1,3,4-oxadiazole-2,5-diyl group, 1,3,4-thiadiazole-2,5-diyl group, and 1,3-thiazole-2.
• the hydrogen atom in the divalent aromatic heterocyclic group is an alkyl group, an alkoxy group, an alkylthio group, a substituted carbonyl group, a substituted carboxyl group, an aryl group, an aryloxy group, an arylthio group, an aralkyl group, or a monovalent aromatic heterocyclic ring.
• Ar 1 examples of the divalent group in which two or more arylene groups, which are the same or different, are directly connected, include biphenyl-4,4′-diyl group, biphenyl-3,4′-diyl group, biphenyl-3,3′-.
• Biphenyldiyl groups such as diyl groups; and terphenyldiyl groups such as [1,1 ′; 4 ′, 1 ′′] terphenyl-4,4 ′′ -diyl groups.
• Ar 1 And the hydrogen atom in the divalent group in which two or more arylene groups, which are the same or different, are directly connected, is an alkyl group, an alkoxy group, an alkylthio group, a substituted carbonyl group, a substituted carboxyl group, an aryl group, an aryloxy group, an arylthio group Group, aralkyl group, monovalent aromatic heterocyclic group, fluorine atom, cyano group and the like.
• Ar 1 As 1,4-phenylene group, 1,3-phenylene group, naphthalene-1,4-diyl group, naphthalene-1,5-diyl group, naphthalene-2,6-diyl group, anthracene-2,6- Diyl group, anthracene-9,10-diyl group, phenanthrene-2,7-diyl group, 9,9-dialkylfluorene-2,7-diyl group, 9,9-diarylfluorene-2,7-diyl group, 7 , 7-dialkyl-benzo [c] fluorene-5,9-diyl group, 7,7-diaryl-benzo [c] fluorene-5,9-diyl group, 6,6,12,12-tetraalkyl-indeno [ 1,2-b] fluorene-2,8-diyl group, 6,6,12,12-tetraalkyl
• 1,4-phenylene group, 1,3-phenylene group, biphenyl-4,4′-diyl group, biphenyl-3,4′-diyl group, biphenyl-3, A 3′-diyl group is particularly preferred.
• Ar 2 And Ar 3 From the viewpoint of heat resistance and ease of synthesis of the polymer compound of the present invention, 1,4-phenylene group, 1,3-phenylene group, anthracene-9,10-diyl group, 9,9-dialkylfluorene A -2,7-diyl group and a 9,9-diarylfluorene-2,7-diyl group are preferred.
• Ar 4 And Ar 5 The aryl group and monovalent aromatic heterocyclic group represented by 2 Are the same as those described and exemplified as the monovalent aromatic heterocyclic group.
• Ar 4 And Ar 5 As, from the viewpoint of heat resistance of the polymer compound of the present invention, an aryl group substituted with an alkyl group, an alkoxy group or an aryl group, or an unsubstituted aryl group is preferable, and an aryl group substituted with an alkyl group or an aryl group An unsubstituted aryl group is more preferable, a phenyl group substituted with an alkyl group or an aryl group, an unsubstituted phenyl group, a 1-naphthyl group substituted with an alkyl group or an aryl group, an unsubstituted 1-naphthyl group, More preferred are a 2-naphthyl group substituted with an alkyl group or an aryl group,
• Ar 2 And Ar 3 Is a phenylene group, Ar is located in the ortho position as seen from the nitrogen atom bonded to the phenylene group.
• Ar 2 And Ar 3 A carbazole ring formed directly by 2 And Ar 3 A phenoxazine ring in which and are bonded by —O—, Ar 2 And Ar 3 Toga-C (R 6 ) (R 6 )-And the like, and a phenoxazine ring is preferable from the viewpoint of luminous efficiency.
• R 6 Are the same as those described and exemplified as the alkyl group in the description of the substituent.
• R 6 An aryl group represented by Ar is Ar 2 And Ar 3 It is the same as what was demonstrated and illustrated as an aryl group represented by these.
• R 6 The monovalent aromatic heterocyclic group represented by R is R 2 In the description of the group represented by the formula, it is the same as described and exemplified as the monovalent aromatic heterocyclic group.
• R 6 The group represented by is preferably an alkyl group or an aryl group.
• group represented by Formula (2) group represented by following formula (2-000) and (2-100) is preferable.
• Ar 4 And Ar 5 Represents the same meaning as described above.
• Examples of the group represented by the formula (2-000) include groups represented by the following formulas (2-001) to (2-008); a hydrogen atom in these groups is an alkyl group, an alkoxy group, or an alkylthio group.
• the bond coming out of the aromatic ring represents the bond as it is or represents a bond via an arylene group.
• Examples of the group represented by the formula (2-100) include groups represented by the following formulas (2-101) to (2-108); a hydrogen atom in these groups is an alkyl group, an alkoxy group, or an alkylthio group.
• the bond coming out of the aromatic ring represents the bond as it is or represents a bond via an arylene group.
• Other groups represented by the formula (2) include groups represented by the following formulas (2-201) to (2-208) and (2-301) to (2-308);
• the hydrogen atom in the group is an alkyl group, alkoxy group, alkylthio group, substituted carbonyl group, substituted carboxyl group, aryl group, aryloxy group, arylthio group, aralkyl group, monovalent aromatic heterocyclic group, fluorine atom and cyano group
• the bond coming out of the aromatic ring represents the bond as it is or represents a bond via an arylene group.
• the structural unit represented by the formula (1a) is preferably a structural unit represented by the following formula (1) from the viewpoint of ease of synthesis.
• R 1 And R 2 Represents the same meaning as described above.
• R 3a , R 4a , R 5a , R 3b , R 4b And R 5b Each independently represents a hydrogen atom, an alkyl group, an aryl group, a monovalent aromatic heterocyclic group, -N (R 8 ) (R 9 ), A fluorine atom or a cyano group.
• R 8 And R 9 Each independently represents a hydrogen atom, an alkyl group, an aryl group, or a monovalent aromatic heterocyclic group.
• R 3a , R 4a , R 5a , R 3b , R 4b , R 5b , R 8 And R 9 The hydrogen atom in the aryl group and monovalent aromatic heterocyclic group represented by the following are alkyl groups, alkoxy groups, alkylthio groups, substituted carbonyl groups, substituted carboxyl groups, aryl groups, aryloxy groups, arylthio groups, aralkyls, respectively.
• Group, monovalent aromatic heterocyclic group, fluorine atom or cyano group may be substituted.
• R 3a And R 4a , R 3b And R 4b , R 3a And R 3b And R 8 And R 9 Each may be taken together to form a ring.
• R 3a , R 4a , R 5a , R 3b , R 4b , R 5b , R 8 And R 9 are the same as those described and exemplified as the alkyl group and aryl group in the description of the substituent.
• R 3a , R 4a , R 5a , R 3b , R 4b , R 5b , R 8 And R 9 The monovalent aromatic heterocyclic group represented by R is R 2 In the description of the group represented by the formula, it is the same as described and exemplified as the monovalent aromatic heterocyclic group.
• R 3b , R 4b , R 5b , R 8 And R 9 An alkyl group, an alkoxy group, an alkylthio group, a substituted carbonyl group, a substituted carboxyl group, an aryl group, an aryloxy group, an arylthio group, an aralkyl group, and a monovalent aromatic heterocyclic ring.
• the groups are the same as those illustrated and described in the description of substituents.
• R 8 -N (R 8 ) (R 9 ) are represented by diphenylamino group, di-4-tolylamino group, di-3-tolylamino group, di- (4-t-butylphenyl) amino group, di- (4-hexylphenyl) amino group Bis ((3,5-di-t-butyl) phenyl) amino group, phenyl-1-naphthylamino group, phenyl-2-naphthylamino group, and the like.
• R 3a , R 4a , R 5a , R 3b , R 4b And R 5b From the viewpoint of ease of synthesis of the polymer compound of the present invention, a hydrogen atom, an alkyl group, and an aryl group are preferable, and a hydrogen atom is more preferable.
• the hydrogen atom in these groups is an alkyl group, alkoxy group, alkylthio group, substituted carbonyl group, substituted carboxyl group, aryl group, aryloxy group , An arylthio group, an aralkyl group, a monovalent aromatic heterocyclic group, a group substituted with a group selected from the group consisting of a fluorine atom and a cyano group.
• the polymer compound of the present invention further includes at least one structural unit selected from the group consisting of structural units represented by the following formulas (3) to (5) May be included.
• Ar 8 And Ar 16 are each independently an arylene group, a divalent aromatic heterocyclic group, or two or more identical or different groups selected from the group consisting of the arylene group and the divalent aromatic heterocyclic group. Represents a valent group.
• Ar 9 , Ar 10 , Ar 11 And Ar 12 Each independently represents an arylene group or a divalent group in which two or more identical or different arylene groups are directly connected.
• Ar 13 , Ar 14 And Ar 15 Each independently represents an aryl group or a monovalent aromatic heterocyclic group.
• Ar 8 And Ar 16 The hydrogen atoms in the arylene group, divalent aromatic heterocyclic group and divalent group represented by the formulas are an alkyl group, an alkoxy group, an alkylthio group, a substituted carbonyl group, a substituted carboxyl group, an aryl group, and an aryloxy group, respectively.
• the hydrogen atom in the group represented by each represents an alkyl group, an alkoxy group, an alkylthio group, a substituted carbonyl group, a substituted carboxyl group, an aryl group, an aryloxy group, an arylthio group, an aralkyl group, and a monovalent aromatic heterocyclic group.
• m and mm are each independently 0 or 1.
• R 7 Represents a hydrogen atom, an alkyl group, an aryl group, a monovalent aromatic heterocyclic group, a fluorine atom or a cyano group.
• R 7 The group represented by may have a substituent.
• Ar 10 , Ar 11 , Ar 14 And Ar 15 When there are a plurality of them, they may be the same or different.
• R 6 , R 8 And R 9 Represents the same meaning as described above.
• the polymer compound of the present invention Preferably contains a structural unit represented by the formula (3).
• the arylene group represented by the formula means an atomic group obtained by removing two hydrogen atoms from an aromatic hydrocarbon, and includes a group having a condensed ring.
• the arylene group usually has 6 to 60 carbon atoms, preferably 6 to 48 carbon atoms, more preferably 6 to 30 carbon atoms, and still more preferably 6 to 14 carbon atoms.
• Arylene groups include 1,4-phenylene groups, 1,3-phenylene groups, 1,2-phenylene groups and the like; naphthalene-1,4-diyl groups, naphthalene-1,5-diyl groups, naphthalene- Naphthalenediyl group such as 2,6-diyl group; anthracene such as anthracene-1,4-diyl group, anthracene-1,5-diyl group, anthracene-2,6-diyl group, anthracene-9,10-diyl group Diyl group; phenanthrene diyl group such as phenanthrene-2,7-diyl group; dihydrophenanthrene diyl group such as 4,5-dihydrophenanthrene-2,7-diyl group; naphthacene-1,7-diyl group, naphthacene-2,
• a perylenedi group such as perylene-2,5-diyl group, perylene-2,8-diyl group, perylene-3,9-diyl group, perylene-3,10-diyl group, 7H-benzo [c] Benzofluorenediyl groups such as fluorene-5,9-diyl group, dihydroindenofluorenediyl groups such as 6,12-dihydro-indeno [1,2-b] fluorene-2,8-diyl group, etc. It is done.
• the hydrogen atom in these arylene groups is alkyl group, alkoxy group, alkylthio group, substituted carbonyl group, substituted carboxyl group, aryl group, aryloxy group, arylthio group, aralkyl group, monovalent aromatic heterocyclic group, -N (R 8 ) (R 9 ), May be substituted with a fluorine atom or a cyano group.
• Ar 8 Is different from the group represented by the formula (1a).
• Ar 8 The divalent aromatic heterocyclic group represented by is an atomic group obtained by removing two hydrogen atoms from an aromatic heterocyclic compound, and includes a group having a condensed ring.
• the divalent aromatic heterocyclic group usually has 3 to 60 carbon atoms, preferably 3 to 20 carbon atoms. The carbon number does not include the carbon number of the substituent.
• Examples of the divalent aromatic heterocyclic group include oxadiazole-2,5-diyl group; thiadiazole-2,5-diyl group; thiazolediyl group such as thiazole-2,5-diyl group; oxazole-2,5 An oxazole diyl group such as a diyl group; a thiophene diyl group such as a thiophene-2,5-diyl group; a pyrrole diyl group such as a pyrrole-2,5-diyl group; a furanyl such as a furan-2,5-diyl group Groups; pyridinediyl groups such as pyridine-2,5-diyl group and pyridine-2,6-diyl group; pyrazin
• the hydrogen atom in these divalent aromatic heterocyclic groups is an alkyl group, alkoxy group, alkylthio group, substituted carbonyl group, substituted carboxyl group, aryl group, aryloxy group, arylthio group, aralkyl group, monovalent aromatic group.
• Ar 8 are preferably 1,4-phenylene group, 1,3-phenylene group, naphthalene-1,4-diyl group, naphthalene-1,5-diyl group, naphthalene-2,6-diyl group, anthracene-2, 6-diyl group, anthracene-9,10-diyl group, fluorene-2,7-diyl group, fluorene-3,6-diyl group, pyrene-1,6-diyl group, pyrene-1,8-diyl group, Perylene-3,9-diyl group, 7H-benzo [c] fluorene-5,9-diyl group, 6,12-dihydro-indeno [1,2-b] fluorene-2,8-diyl group, oxadiazole -2,5-diyl group, thiadiazole-2,5-diyl group,
• -Diyl group naphthalene-2,6-diyl group, anthracene-2,6-diyl group, anthracene-9,10-diyl group, fluorene-2,7-diyl group, pyrene-1,6-diyl group, perylene -3,9-diyl group, 7H-benzo [c] fluorene-5,9-diyl group, 6,12-dihydro-indeno [1,2-b] fluorene-2,8-diyl group, quinoline 2,6-diyl group, quinoxaline-5,8-diyl group, phenoxazine-3,7-diyl group, phenothiazine-3,7-diyl group, benzo [1,2,5] thiadiazole-4,7-diyl It is a group.
• the hydrogen atom in these groups is an alkyl group, alkoxy group, alkylthio group, substituted carbonyl group, substituted carboxyl group, aryl group, aryloxy group, arylthio group, aralkyl group, monovalent aromatic heterocyclic group, -N ( R 8 ) (R 9 ), A fluorine atom, a cyano group or the like.
• the divalent group represented by any one of the following formulas (3b) and (3c) is preferable, and the polymer compound of the present invention From the viewpoint of the luminous efficiency of the light-emitting device obtained by using a divalent group, a divalent group represented by any one of the following formulas (3b), (3d), and (3e) is preferable.
• the divalent group represented is particularly preferable.
• R 10 Is an alkyl group, an alkoxy group, an alkylthio group, a substituted carbonyl group, a substituted carboxyl group, an aryl group, an aryloxy group, an arylthio group, an aralkyl group, a monovalent aromatic heterocyclic group, -N (R 8 ) (R 9 ), A fluorine atom or a cyano group.
• f represents an integer of 0 to 4.
• R 10 When two or more exist, they may be the same or different.
• R 11 And R 12 Each independently represents a hydrogen atom, an alkyl group, an aryl group, an aralkyl group or a monovalent aromatic heterocyclic group.
• R 11 And R 12 Together may form a ring.
• R 13 And R 14 are each independently a hydrogen atom, alkyl group, alkoxy group, alkylthio group, substituted carbonyl group, substituted carboxyl group, aryl group, aryloxy group, arylthio group, aralkyl group, monovalent aromatic heterocyclic group, -N ( R 8 ) (R 9 ), A fluorine atom or a cyano group.
• R 15 Represents a hydrogen atom, an alkyl group, an aryl group, a monovalent aromatic heterocyclic group or an aralkyl group.
• R 16 Represents a hydrogen atom, an alkyl group, an aryl group, a monovalent aromatic heterocyclic group or an aralkyl group.
• R 10 Is preferably an alkyl group, an alkoxy group, a substituted carbonyl group, an aryl group, an aryloxy group, an aralkyl group, a monovalent aromatic heterocyclic group, -N (R 8 ) (R 9 And more preferably an alkyl group, an alkoxy group or an aryl group.
• R 10 The monovalent aromatic heterocyclic group represented by R is R 2 This is the same as explained and exemplified in the section of monovalent aromatic heterocyclic group as the group represented by formula (1).
• f is preferably an integer of 1 to 4, more preferably 1, 2, and still more preferably 2.
• R in the formula (3b) 11 And R 12 , R in formula (3d) 15 And R in formula (3e) 16 Is preferably an alkyl group, an aryl group, or a monovalent aromatic heterocyclic group, and more preferably an alkyl group or an aryl group.
• the alkyl group, aryl group and aralkyl group are R 2 These are the same as those described and exemplified as the substituent.
• the monovalent aromatic heterocyclic group represented by R is R 2 This is the same as explained and exemplified in the section of monovalent aromatic heterocyclic group as the group represented by formula (1).
• R 13 And R 14 Is preferably a hydrogen atom or an alkyl group.
• the alkyl group is R 2 These are the same as those described and exemplified as the substituent.
• R 13 , R 14 The monovalent aromatic heterocyclic group represented by R is R 2 This is the same as explained and exemplified in the section of monovalent aromatic heterocyclic group as the group represented by formula (1).
• -The structural unit represented by formula (4) From the viewpoint of improving the heat resistance of the polymer compound of the present invention, the luminous efficiency of the light-emitting device obtained using the polymer compound, or the heat resistance, the polymer compound of the present invention is represented by the formula (4). It is preferable that the structural unit is included.
• Ar 9 ⁇ Ar 12 Or a divalent group in which two or more arylene groups, which are the same or different, are directly connected, is represented by Ar in the formula (2) 1 It is the same as described and exemplified as.
• Ar 13 ⁇ Ar 15 The monovalent aromatic heterocyclic group represented by the formula: Ar in formula (2) 2 And Ar 3 It is the same as described and exemplified as.
• Preferred examples of the structural unit represented by the formula (4) include structural units represented by the following formulas (4a) to (4d).
• R a Is a hydrogen atom, alkyl group, alkoxy group, alkylthio group, substituted carbonyl group, substituted carboxyl group, aryl group, aryloxy group, arylthio group, aralkyl group, monovalent aromatic heterocyclic group, fluorine atom or cyano group.
• a hydrogen atom or an alkyl group Preferably a hydrogen atom or an alkyl group.
• Multiple R a May be the same or different.
• An alkyl group, an alkoxy group, an alkylthio group, a substituted carbonyl group, a substituted carboxyl group, an aryl group, an aryloxy group, an arylthio group, an aralkyl group, and a monovalent aromatic heterocyclic group are represented by R in the formula (1a). 2 Is the same as described and exemplified in the section of the substituent in the case where has a substituent.
• the structural unit represented by Formula (5) The polymer compound of the present invention may contain a structural unit represented by the formula (5) from the viewpoint of adjusting the chromaticity of a light-emitting element using the polymer compound.
• Ar 16 A divalent group in which two or more identical or different groups selected from the group consisting of an arylene group, a divalent aromatic heterocyclic group, the arylene group and the divalent aromatic heterocyclic group represented by Is Ar 8 It is the same as described and exemplified as.
• X 1 R which can be included in 7 Is preferably a hydrogen atom, an alkyl group, or an aryl group, and more preferably a hydrogen atom or an aryl group.
• the alkyl group and aryl group may have a substituent.
• the alkyl group and the aryl group are represented by R in the formula (1a). 2 These are the same as those described and exemplified as the substituent.
• R 7 The monovalent aromatic heterocyclic group represented by R is R 2 This is the same as explained and exemplified in the section of monovalent aromatic heterocyclic group as the group represented by formula (1).
• structural unit represented by the formula (5) structural units represented by the following formulas (5a) to (5k) are preferable.
• -Polymer compound of the present invention In the polymer compound of the present invention, the number of moles of the structural unit represented by the formula (1a) is 0.1 to 100% with respect to the total number of moles of all the structural units, from the viewpoint of light emission efficiency of the light-emitting element. Is preferably 0.5 to 50%, more preferably 1 to 20%.
• the total number of moles of the structural units represented by the formulas (1a) and (3) to (5) with respect to the total moles of all the structural units is preferably 90 to 100%, and preferably 95 to 100%. Is more preferably 98 to 100%, and particularly preferably 100%.
• the total number of moles of the structural units represented by the formulas (1a), (3) and (4) is preferably 90 to 100% with respect to the total number of moles of all the structural units. 95 to 100% is more preferable.
• the polymer compound of the present invention includes, in addition to the structural unit represented by the formula (1a), at least one structural unit selected from the group consisting of the structural units represented by the formulas (3) and (4). The high molecular compound which becomes is preferable.
• the polymer compound of the present invention includes, in addition, a polymer compound composed of a structural unit represented by formula (1); a polymer compound composed of a structural unit represented by formulas (1) and (3a); (1), a polymer compound composed of structural units represented by (3a) and (3b); a polymer compound composed of structural units represented by formulas (1), (3a) and (4a); ), (3a), (3b) and a polymer compound composed of structural units represented by (4a); a polymer compound composed of structural units represented by formulas (1) and (3b); formula (1), A polymer compound composed of structural units represented by (3b) and (3c); a polymer compound composed of structural units represented by formulas (1), (3b), (3c) and (3d); ), (3b), (3c) and (4d), a polymer compound composed of structural units represented by formula (1) , (3b) and a polymer compound composed of structural units represented by (3d); a polymer compound composed of structural units represented by formulas (1), (3b) and (3e); 3b) and a polymer compound composed
• polymer compound of the present invention include the following polymer compounds.
• v / w, v ′ / w ′ / x ′, v ′′ / w ′′ / x ′′, v ′ ′′ / w ′ ′′ / x ′ ′′, v IV / W IV / X IV , V V / W V / X V Represents the molar ratio of two or three structural units.
• v is a number from 0 to 0.99
• w is a number from 0.01 to 1
• v + w 1.
• v ′ is a number from 0 to 0.98
• w ′ is a number from 0.01 to 0.99
• x ′ is a number from 0.01 to 0.99
• v ′ + w '+ X' 1.
• v ′′ is a number from 0 to 0.98
• w ′′ is a number from 0.01 to 0.99
• x ′′ is a number from 0.01 to 0.50
• v ′′ + w ′′ + x ′′ 1.
• v ′ ′′ is a number from 0 to 0.98, w ′ ′′ is a number from 0.01 to 0.99, and x ′ ′′ is a number from 0.01 to 0.50.
• the terminal group of the polymer compound of the present invention is stable if the polymerization active group remains as it is because the polymer compound may be used for the production of a light-emitting device, so that the light emission characteristics and life may be reduced. It is preferably a group.
• the terminal group is preferably conjugated to the main chain, and preferably bonded to an aryl group or a monovalent aromatic heterocyclic group via a carbon-carbon bond.
• the structural unit represented by the formula (1a) and the structural units represented by the formulas (3) to (5) may be used alone or in combination of two or more. It may be included.
• the polymer compound of the present invention may have any shape such as linear polymer, branched polymer, hyperbranched polymer, cyclic polymer, comb polymer, star polymer, network polymer, etc. It may be a polymer having any composition and regularity such as a homopolymer, an alternating copolymer, a periodic copolymer, a random copolymer, a block copolymer, and a graft copolymer.
• the polymer compound of the present invention is useful as a light-emitting material, a charge transport material, and the like. When used, the polymer compound may be used in combination with other compounds as a composition described later.
• the number average molecular weight (Mn) in terms of polystyrene by gel permeation chromatography (hereinafter referred to as “GPC”) of the polymer compound of the present invention is usually 1 ⁇ 10. 3 ⁇ 1 ⁇ 10 8 And preferably 1 ⁇ 10 4 ⁇ 1 ⁇ 10 6 It is.
• the weight average molecular weight (Mw) in terms of polystyrene of the polymer compound of the present invention is usually 1 ⁇ 10.
• the glass transition temperature of the polymer compound of the present invention is preferably 100 ° C. or higher from the viewpoints of durability to various processes for producing a light-emitting element and the like, stability due to heat generation during driving of the light-emitting element, and heat resistance.
• the polymer compound of the present invention usually emits fluorescence or phosphorescence in a solid state and is useful as a material for a light emitting device.
• a light-emitting element using this polymer compound is a high-performance light-emitting element that can be driven with high luminous efficiency. Therefore, the light emitting element is useful for a display device such as a backlight of a liquid crystal display, a curved or flat light source for illumination, a segment type display element, a dot matrix flat panel display.
• the polymer compound of the present invention comprises a dye for laser, an organic solar cell material, an organic semiconductor for an organic transistor, a conductive thin film, a conductive thin film material such as an organic semiconductor thin film, a luminescent thin film that emits fluorescence or phosphorescence. It can also be used as a material.
• the polymer compound of the present invention may contain, for example, a monomer represented by the formula (A) having a functional group suitable for the polymerization reaction used, according to the following formulas (M-1) to (M- 3) Polymerization such as known aryl coupling using a compound selected from the group consisting of compounds represented by 3), if necessary, dissolved in an organic solvent and using an alkali, a suitable catalyst, or a compound serving as a ligand It can be synthesized by polymerization or copolymerization by a method.
• Ar 8 , X a And X b Has the same meaning as described above.
• R 20 , R 21 And R 22 Each of the alkyl groups represented by the formula may independently be linear, branched or cyclic, and usually has 1 to 20 carbon atoms, preferably 1 to 15 carbon atoms, and more preferably 1 to 10 carbon atoms.
• R 20 The alkyl group represented by R is R 2 These are the same as those described and exemplified in the description of the substituents.
• R 20 The aryl group represented by R is R 2
• a phenyl group, 4-tolyl group, 4-methoxy A phenyl group, a 4-nitrophenyl group, a 3-nitrophenyl group, a 2-nitrophenyl group, and a 4-trifluoromethylphenyl group are particularly preferable.
• —O—S ( ⁇ O) 2 R 20 examples of the group represented by the formula include a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, a phenylsulfonyloxy group, a 4-methylphenylsulfonyloxy group, and a 4-trifluoromethylphenylsulfonyloxy group.
• -B OR 21
• Examples of the group represented by include groups represented by the following formulas.
• -BF 4 Q 1 Examples of the group represented by include groups represented by the following formulas.
• -Sn (R 22 ) 3 examples of the group represented by the formula include trimethylstannanyl group, triethylstannanyl group, tributylstannanyl group and the like.
• the compounds represented by the formula (A) and the formulas (M-1) to (M-3) may be synthesized and isolated in advance, or may be synthesized in a reaction system and used as they are.
• the monomer before polymerization is purified by distillation, sublimation purification, recrystallization, etc. It is preferable to do.
• the method of polymerizing and the method of polymerizing with Ni (0) catalyst are preferable from the viewpoint of easy synthesis of raw materials and ease of operation of the polymerization reaction, and from the viewpoint of easy control of the structure of the polymer compound, polymerization is performed by Suzuki coupling reaction. The method of doing is more preferable.
• X a And X b Is a bromine atom, an iodine atom, a chlorine atom, -B (OR from the viewpoint of ease of synthesis of the polymer compound of the present invention.
• condensation polymerization when a method of polymerizing by a Suzuki coupling reaction is selected as the method of condensation polymerization, the synthesis of the compounds represented by the formulas (A) and (M-1) to (M-3) From the viewpoint of ease of use and ease of handling, bromine atom, iodine atom, chlorine atom, -B (OR 21 ) 2 And more preferably a bromine atom, -B (OR 21 ) 2 More preferably.
• the condensation polymerization method include a method in which the compounds represented by the formulas (A) and (M-1) to (M-3) are reacted with an appropriate catalyst or an appropriate base, if necessary.
• the formulas (A), (M-1) to ( X which the compound represented by M-3) has a And X b
• the total number of moles of a bromine atom, an iodine atom, and a chlorine atom represented by -B (OR 21 ) 2 Is preferably 0.95 to 1.05, and more preferably 0.98 to 1.02.
• transition metals such as palladium complexes such as palladium [tetrakis (triphenylphosphine)], [tris (dibenzylideneacetone)] dipalladium, palladium acetate, dichlorobistriphenylphosphine palladium, etc.
• a catalyst comprising a complex and, if necessary, a ligand such as triphenylphosphine, tri (t-butylphosphine), tricyclohexylphosphine and the like can be mentioned.
• Ni (0) catalyst nickel [tetrakis (triphenylphosphine)], [1,3-bis (diphenylphosphino) propane] dichloronickel, [bis (1,4-cyclooctadiene)] nickel, etc.
• a catalyst comprising a transition metal complex such as a nickel complex and a ligand such as triphenylphosphine, tri (t-butylphosphine), tricyclohexylphosphine, diphenylphosphinopropane, bipyridyl, if necessary.
• the catalyst may be used after being synthesized in advance, or may be prepared in a reaction system and used as it is.
• a catalyst may be used individually by 1 type, or may use 2 or more types together. When a catalyst is used, the amount of the catalyst may be an effective amount as a catalyst.
• the amount of the transition metal compound relative to the total number of moles of the compounds represented by the formulas (A) and (M-1) to (M-3) is usually 0.00001 to 3 molar equivalents, preferably 0.8. It is 0.0005 to 0.5 molar equivalent, and more preferably 0.0001 to 0.2 molar equivalent. In the polymerization by the Suzuki coupling reaction, the reaction is usually performed in the presence of a base.
• Bases include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, potassium fluoride, cesium fluoride, tripotassium phosphate, tetrabutylammonium fluoride, tetrabutylammonium chloride, tetrabutylammonium bromide, tetrahydroxide hydroxide
• An organic base such as butylammonium may be mentioned.
• the amount is usually 0.5 to 20 molar equivalents relative to the total number of moles of the compounds represented by formulas (A) and (M-1) to (M-3). And preferably 1 to 10 molar equivalents.
• the condensation polymerization may be carried out in the absence of a solvent or in the presence of a solvent, but is usually carried out in the presence of an organic solvent.
• organic solvent include toluene, xylene, mesitylene, tetrahydrofuran, 1,4-dioxane, dimethoxyethane, N, N-dimethylacetamide, N, N-dimethylformamide and the like.
• An organic solvent may be used individually by 1 type, or may use 2 or more types together.
• the amount of the organic solvent used is such that the total concentration of the compounds represented by formulas (A) and (M-1) to (M-3) is different from that of the organic solvent and formulas (A) and (M-1) to (M-).
• the amount is usually 0.1 to 90% by weight, preferably 1 to 50% by weight, more preferably 2 to 30% by weight, based on the total weight of the compound represented by 3).
• the reaction temperature of the condensation polymerization is preferably ⁇ 100 to 200 ° C., more preferably ⁇ 80 to 150 ° C., and further preferably 0 to 120 ° C.
• the reaction time depends on conditions such as the reaction temperature, but is usually 1 hour or longer, preferably 2 to 500 hours.
• Condensation polymerization is carried out according to the formula X a And X b -MgY 1 Is carried out under dehydration conditions.
• a compound represented by the following formula (M-4) may be used as a chain terminator in order to avoid leaving a polymerization active group at the terminal of the polymer compound of the present invention.
• M-4 a compound represented by the following formula (M-4)
• M-4 may be used as a chain terminator in order to avoid leaving a polymerization active group at the terminal of the polymer compound of the present invention.
• Ar 24 Represents an aryl group or a monovalent aromatic heterocyclic group.
• R 20 Represents an alkyl group, or an aryl group optionally substituted with an alkyl group, an alkoxy group, a nitro group, a fluorine atom or a cyano group.
• R 21 And R 22 Each independently represents a hydrogen atom or an alkyl group. 2 R 21 May be the same or different, and may together form a ring.
• R 22 May be the same or different, and may together form a ring.
• Q 1 Represents a monovalent cation of lithium, sodium, potassium, rubidium or cesium.
• Y 1 Represents a bromine atom, an iodine atom or a chlorine atom.
• X c The atom or group represented by X is X a And X b The same as those explained and exemplified as the respective atoms or groups represented by In formula (M-4), Ar 24
• the aryl group and monovalent aromatic heterocyclic group represented by 2 Are the same as those described and exemplified as the monovalent aromatic heterocyclic group.
• the post-treatment of the condensation polymerization can be performed by a known method.
• the post-treatment can be performed, for example, by a method of adding a reaction solution obtained by condensation polymerization to a lower alcohol such as methanol and filtering and drying the deposited precipitate.
• a reaction solution obtained by condensation polymerization obtained by condensation polymerization to a lower alcohol such as methanol
• the polymer compound can be purified by ordinary methods such as recrystallization, continuous extraction with a Soxhlet extractor, column chromatography and the like.
• the purity affects the device performance such as light-emitting properties, and therefore, it is preferable to perform purification treatment such as reprecipitation purification and fractionation by chromatography after condensation polymerization. .
• Examples of the compound represented by the formula (A) include structural units represented by the formula (1) (for example, the formulas (1-001) to (1-005), (1-101) to (1-106), (The structural units represented by (1-201) to (1-202) and (1-301) to (1-303)), and one of the two bonds in these substituents is X a The other group is X b The compound substituted by group represented by these is mentioned.
• -Method for producing compound represented by formula (A) As shown in the following scheme 1, for example, the compound represented by the formula (A) includes a compound represented by the following formula (B) and a compound represented by the following formula (C) as necessary.
• the compound represented by the formula (B) can be synthesized, for example, by reacting a fluorenone derivative with a Grignard reagent or an organolithium reagent.
• the amount of the compound represented by the formula (C) is usually 0.8 to 2 mol with respect to 1 mol of the compound represented by the formula (B), but is represented by the formula (A) to be obtained. From the viewpoint of easy purification of the compound, 0.9 to 1.5 mol is preferable.
• the acid examples include boron trifluoride diethyl ether complex, trifluoromethanesulfonic acid, methanesulfonic acid, trifluoroacetic acid, sulfuric acid, polyphosphoric acid and the like, and boron trifluoride diethyl ether complex is preferable.
• the amount of acid used depends on the type, for example, when boron trifluoride diethyl ether complex is used, the amount of boron trifluoride diethyl ether complex used is 1 mol of the compound represented by formula (B). On the other hand, from the viewpoint of reactivity and economy, it is usually 1 to 10 moles, preferably 1 to 2 moles.
• the solvent examples include organic solvents such as toluene, xylene, mesitylene, chlorobenzene, o-dichlorobenzene, dichloromethane, chloroform, and carbon tetrachloride.
• organic solvents such as toluene, xylene, mesitylene, chlorobenzene, o-dichlorobenzene, dichloromethane, chloroform, and carbon tetrachloride.
• the solvent is preferably chlorobenzene, o-dichlorobenzene, dichloromethane, chloroform, or carbon tetrachloride, and more preferably dichloromethane, chloroform, or carbon tetrachloride.
• the reaction is preferably carried out under light shielding from the viewpoint of the stability of the compound represented by formula (B) and the compound represented by formula (A).
• the reaction temperature is usually ⁇ 50 to 300 ° C., but when a combination of boron trifluoride diethyl ether complex and an organic solvent is used, it is preferably ⁇ 20 to 100 ° C.
• the reaction may be carried out under reflux. After completion of the reaction, water, alcohol, etc. are added to stop the reaction, and after removing unnecessary components such as water, alcohol, etc.
• the polymer compound of the present invention can be used as a composition by mixing with other components, for example, in combination with at least one selected from the group consisting of a hole transport material, an electron transport material and a light emitting material. It can be used as a light emitting material, a hole transport material, or an electron transport material.
• the ratio of at least one selected from the group consisting of a hole transport material, an electron transport material and a light emitting material and the polymer compound of the present invention is the ratio when the composition of the present invention is used for the light emitting material.
• the weight of the hole transport material, the electron transport material, and the light emitting material is usually 1 to 400 parts by weight, preferably 5 to 150 parts by weight, with respect to 100 parts by weight of the polymer compound of the invention.
• the number average molecular weight in terms of polystyrene of the composition of the present invention is usually 1 ⁇ 10. 3 ⁇ 1 ⁇ 10 8 And preferably 1 ⁇ 10 4 ⁇ 1 ⁇ 10 6 It is.
• the weight average molecular weight in terms of polystyrene of the composition of the present invention is usually 1 ⁇ 10.
• the average molecular weight of the composition of the present invention refers to a value obtained by analyzing the composition by GPC.
• the solution of the present invention is a solution containing the polymer compound of the present invention and a solvent, and a solution comprising the composition of the present invention containing a solvent. This solution is useful for a printing method or the like, and is generally sometimes referred to as an ink or an ink composition.
• the solvent of the present invention comprises a hole transport material (a material used for a hole transport layer described later), an electron transport material (a material used for an electron transport layer described later), a light emitting material, a stabilizer, a thickener (viscosity).
• a high molecular weight compound for increasing the viscosity a low molecular weight compound for decreasing the viscosity
• a surfactant an antioxidant
• a high molecular weight compound other than the high molecular compound and the like.
• Each component contained in the solution of the present invention may be a single type or a combination of two or more types.
• the ratio of the polymer compound of the present invention in the solution of the present invention is usually 0.1 to 99 parts by weight, preferably 0.5 to 40 parts by weight, when the total solution is 100 parts by weight. More preferably, it is 0.5 to 20 parts by weight.
• the viscosity of the solution of the present invention can be adjusted depending on the type of printing method. However, in the case where the solution such as an ink jet printing method passes through a discharge device, in order to prevent clogging or flight bending at the time of discharge. Furthermore, it is preferably in the range of 1 to 20 mPa ⁇ s at 25 ° C.
• the thickener is not particularly limited as long as it is soluble in the same solvent as the polymer compound of the present invention and does not inhibit light emission or charge transport.
• high molecular weight polystyrene, high molecular weight polymethyl methacrylate, or the like may be used. it can.
• the compound used as the thickener has a polystyrene equivalent weight average molecular weight of 5 ⁇ 10. 5 Preferably, it is 1 ⁇ 10 6 More preferably.
• the antioxidant is for improving the storage stability of the solution of the present invention.
• the antioxidant is not particularly limited as long as it is soluble in the same solvent as the polymer compound of the present invention and does not inhibit light emission or charge transport, and examples thereof include phenolic antioxidants and phosphorus antioxidants.
• the solvent of the solution of the present invention is preferably one that can dissolve or uniformly disperse the solid content as a solute.
• the solvent examples include chlorine solvents such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene and o-dichlorobenzene; ether solvents such as tetrahydrofuran, dioxane and anisole; toluene and xylene Aromatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane, and the like; acetone, methyl ethyl ketone, Ketone solvents such as cyclohexanone, benzophenone and acetophenone; ester solvents such as ethyl acetate, butyl acetate, ethyl cellosolve acetate, methyl benzoate and phenyl
• solvents may be used alone or in combination of two or more.
• Two or more solvents are preferably used in combination from the viewpoints of film formability, device characteristics, and the like, more preferably two to three types are used in combination, and two types are particularly preferably used in combination.
• one of the solvents may be in a solid state at 25 ° C.
• one kind of solvent is preferably a solvent having a boiling point of 180 ° C. or higher, and more preferably 200 ° C. or higher.
• the solution of the present invention is preferably one that can exist as a uniform solution at a temperature lower than the boiling point of the mixed solvent to be used.
• the polymer compound of the present invention is dissolved, and the polymer compound of the present invention is dissolved in one of the two solvents at a concentration of 1% by weight or more at 25 ° C. Particularly preferred.
• the solvent having the highest boiling point is 40 to 90% by weight of the total solvent weight in the solution from the viewpoint of viscosity and film formability. It is preferably 50 to 90% by weight, more preferably 65 to 85% by weight.
• the solution of the present invention may further contain water, metal and a salt thereof, silicon, phosphorus, fluorine, chlorine, bromine and the like in a range of 1 to 1000 ppm by weight.
• the thin film of the present invention contains the polymer compound of the present invention, and is, for example, a luminescent thin film, a conductive thin film, an organic semiconductor thin film, or the like.
• the thin film of the present invention is, for example, a spin coating method, a casting method, a micro gravure coating method, a gravure coating method, a bar coating method, a roll coating method, a wire bar coating method, a dip coating method, a spray coating method, a screen printing method, a flexographic method.
• It can be produced by a printing method, an offset printing method, an inkjet printing method, a capillary coating method, a nozzle coating method, or the like.
• a thin film is produced using the solution of the present invention, since the glass transition temperature of the polymer compound of the present invention contained in the solution is high, it can be baked at a temperature of 100 ° C. or higher, and a temperature of 130 ° C. Even when baked, the device characteristics hardly deteriorate.
• baking can be performed at a temperature of 160 ° C. or higher.
• the light-emitting thin film preferably has a quantum yield of light emission of 30% or more, more preferably 50% or more, and further preferably 60% or more from the viewpoint of device brightness, light emission voltage, and the like. 70% or more is particularly preferable.
• the conductive thin film preferably has a surface resistance of 1 K ⁇ / ⁇ or less, more preferably 100 ⁇ / ⁇ or less, and even more preferably 10 ⁇ / ⁇ or less. Electrical conductivity can be increased by doping the conductive thin film with a Lewis acid, an ionic compound or the like.
• the organic semiconductor thin film has a higher electron mobility or hole mobility of 10 -5 cm 2 / V / second or more is preferable 10 -3 cm 2 / V / second or more is more preferable.
• the light-emitting element of the present invention is a light-emitting element having an electrode composed of an anode and a cathode, and an organic layer containing a polymer compound provided between the electrodes. At least one of the anode and the cathode is usually transparent or translucent.
• the organic layer may be composed of a single layer or may be composed of two or more layers.
• the organic layer When the organic layer is composed of two or more layers, at least one of them contains a polymer compound.
• the organic layer containing the polymer compound usually functions as a light emitting layer, a hole transport layer, and an electron blocking layer, but preferably functions as a light emitting layer.
• other layers may be provided between the anode and the light emitting layer and between the cathode and the light emitting layer.
• each layer may be composed of one layer or two or more layers, and the materials and compounds constituting each layer may be used alone or in combination of two or more. May be used in combination.
• Examples of the layer provided between the anode and the light emitting layer include a hole injection layer, a hole transport layer, and an electron block layer.
• a hole injection layer When only one layer is provided between the anode and the light emitting layer, it is a hole injection layer, and when two or more layers are provided between the anode and the light emitting layer, the layer in contact with the anode is a hole injection layer.
• the other layers are hole transport layers.
• the hole injection layer is a layer having a function of improving hole injection efficiency from the cathode.
• the hole transport layer is a layer having a function of improving hole injection from a hole injection layer or a layer closer to the anode. When the hole injection layer and the hole transport layer have a function of blocking electron transport, these layers are electron blocking layers.
• the layer provided between the cathode and the light emitting layer include an electron injection layer, an electron transport layer, and a hole blocking layer.
• the layer in contact with the cathode is an electron injection layer.
• the other layers are electron transport layers.
• the electron injection layer is a layer having a function of improving electron injection efficiency from the cathode.
• the electron transport layer is a layer having a function of improving electron injection from an electron injection layer or a layer closer to the cathode.
• these layers may be referred to as a hole blocking layer. Having the function of blocking hole transport can be confirmed, for example, by fabricating a device that allows only hole current to flow and reducing the current value.
• Examples of the light emitting device of the present invention include the following structures a) to d).
• Anode / light emitting layer / cathode b) Anode / hole transport layer / light emitting layer / cathode c) Anode / light emitting layer / electron transport layer / cathode d) Anode / hole transport layer / light emitting layer / electron transport layer / cathode (Here, / indicates that each layer is laminated adjacently. The same shall apply hereinafter.) Of the hole transport layer and electron transport layer provided adjacent to the electrode, the one that has the function of improving the charge (hole / electron) injection efficiency from the electrode and has the effect of reducing the drive voltage of the element , Sometimes referred to as a charge injection layer (hole injection layer, electron injection layer).
• a charge injection layer and an insulating layer may be provided adjacent to the electrode in order to improve adhesion with the electrode and improve charge injection from the electrode.
• a thin buffer layer may be inserted at the interface between the charge transport layer and the light emitting layer in order to improve the adhesion at the interface or prevent mixing.
• the order and number of layers to be stacked, and the thickness of each layer can be adjusted in consideration of light emission efficiency and element lifetime. Examples of the light emitting device of the present invention provided with the charge injection layer include the following structures e) to p).
• the material of the anode a film formed using indium oxide, zinc oxide, tin oxide, and a conductive inorganic compound composed of indium tin oxide (ITO), indium zinc oxide, or the like, which is a composite thereof. (NESA etc.), gold, platinum, silver, copper and the like are used, and ITO, indium / zinc / oxide, and tin oxide are preferable.
• ITO indium tin oxide
• tin oxide a conductive inorganic compound composed of indium tin oxide (ITO), indium zinc oxide, or the like, which is a composite thereof. (NESA etc.), gold, platinum, silver, copper and the like are used, and ITO, indium / zinc / oxide, and tin oxide are preferable.
• methods such as a vacuum deposition method, a sputtering method, an ion plating method, and a plating method can be used.
• an organic transparent conductive film such as polyaniline and a derivative thereof, poly
• the thickness of the anode can be selected in consideration of light transmittance and electric conductivity, but is usually 10 nm to 10 ⁇ m, preferably 20 nm to 1 ⁇ m, more preferably 50 nm to 500 nm. .
• Hole injection layer Materials used for the hole injection layer include phenylamine, starburst amine, phthalocyanine, vanadium oxide, molybdenum oxide, ruthenium oxide, aluminum oxide and other oxides, amorphous carbon, polyaniline and its derivatives, polythiophene and Examples thereof include conductive polymers such as derivatives thereof, and polymer compounds of the present invention.
• a polystyrene sulfone is used as necessary to improve the electrical conductivity of the conductive polymer or the polymer compound.
• Anions such as acid ions, alkylbenzene sulfonate ions, camphor sulfonate ions may be doped.
• Hole transport layer Materials used for the hole transport layer include polyvinylcarbazole and derivatives thereof, polysilane and derivatives thereof, polysiloxane derivatives having aromatic amines in the side chain or main chain, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine Derivatives, polyaniline and derivatives thereof, 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, book
• the polymer compound of the invention include polyvinyl carbazole and derivatives thereof, polysilane and derivatives thereof, polysiloxane derivatives having an aromatic amine compound group in the side chain or main chain, polyaniline and derivatives thereof, polythiophene and Polymer hole transport materials such as polyarylamine and derivatives thereof, poly (p-phenylene vinylene) and
• the material used for the hole transport layer is a low molecular weight compound, it is preferably used by being dispersed in a polymer binder.
• film formation from a mixed solution with a polymer binder is exemplified. In some cases, film formation from a solution can be mentioned. The solvent used for film formation from a solution dissolves the material used for the hole transport layer.
• the solvent examples include chlorine solvents such as chloroform, methylene chloride, and dichloroethane; ether solvents such as tetrahydrofuran; aromatic hydrocarbon solvents such as toluene and xylene; ketone solvents such as acetone and methyl ethyl ketone; ethyl acetate, butyl acetate, Examples include ester solvents such as ethyl cellosolve acetate.
• chlorine solvents such as chloroform, methylene chloride, and dichloroethane
• ether solvents such as tetrahydrofuran
• aromatic hydrocarbon solvents such as toluene and xylene
• ketone solvents such as acetone and methyl ethyl ketone
• ethyl acetate butyl acetate
• ester solvents such as ethyl cellosolve acetate.
• a coating method such as a printing method, a flexographic printing method, an offset printing method, and an inkjet printing method can be used.
• the polymer binder those that do not extremely inhibit charge transport are preferable, and those that do not strongly absorb visible light are preferably used.
• the polymer binder include polycarbonate, polyacrylate, polymethyl acrylate, polymethyl methacrylate, polystyrene, polyvinyl chloride, and polysiloxane.
• the thickness of the hole transport layer can be selected in consideration of the drive voltage and light emission efficiency, but it needs to be thick enough so that pinholes do not occur. If it is too thick, the drive voltage of the device will increase. It is not preferable. Therefore, the thickness of the hole transport layer is usually 1 nm to 1 ⁇ m, preferably 2 nm to 500 nm, more preferably 5 nm to 200 nm.
• the light emitting layer is usually formed from an organic compound (low molecular compound or high molecular compound) that emits fluorescence or phosphorescence and a dopant that assists the organic compound as necessary.
• the polymer compound of the present invention cyclopentamine derivative, tetraphenylbutadiene derivative compound, triphenylamine derivative, oxadiazole derivative, pyrazoloquinoline derivative, distyrylbenzene derivative, diester Dye-based materials such as styrylarylene derivatives, pyrrole derivatives, thiophene ring compounds, pyridine ring compounds, anthracene derivatives, perylene derivatives, naphthacene derivatives, quinacridone derivatives, oligothiophene derivatives, trifumarylamine derivatives, oxadiazole dimers, pyrazoline dimers; Metal complexes that emit light from triplet excited states such as iridium complexes and platinum complexes, aluminum quinolinol complexes, benzoquinolinol beryllium complexes, benzoxazolyl zinc complexes, be
• ligand is oxadiazole, thiadiazole, phenylpyridine, phenyl Metal complex materials such as benzimidazole and metal complexes having a quinoline structure; polyparaphenylene vinylene derivatives, polythiophene derivatives, polyparaphenylene derivatives, polysilane derivatives, polyacetylene derivatives, polyfluorene derivatives, polyvinylcarbazole derivatives, the above dye bodies and metals
• Light emitting materials such as polymer materials such as those obtained by polymerizing complex light emitting materials can be used. Among the light emitting materials, materials emitting blue light can be classified into blue fluorescent materials and blue phosphorescent materials.
• blue fluorescent material examples include distyrylarylene derivatives and polymers thereof, oxadiazole derivatives and polymers thereof, polyvinyl carbazole derivatives, polyparaphenylene derivatives, polyfluorene derivatives, and the like. Phenylene derivatives, polyfluorene derivatives and the like.
• blue phosphorescent material examples include iridium complexes. Among the above light emitting materials, materials emitting green light can be classified into green fluorescent materials and green phosphorescent materials.
• green fluorescent material examples include quinacridone derivatives, coumarin derivatives, anthracene derivatives, and polymers thereof, polyparaphenylene vinylene derivatives, polyfluorene derivatives, and the like, preferably polyparaphenylene vinylene derivatives, polyfluorene derivatives, and the like.
• green phosphorescent material examples include iridium complexes. Among the above light emitting materials, materials that emit red light can be classified into red fluorescent materials and red phosphorescent materials.
• red fluorescent material examples include a coumarin derivative and a polymer thereof, a thiophene compound and a polymer thereof, a polyparaphenylene vinylene derivative, a polythiophene derivative, a polyfluorene derivative, and the like, preferably a polyparaphenylene vinylene derivative, a polythiophene derivative, Polyfluorene derivatives and the like.
• red phosphorescent material examples include iridium complexes.
• a dopant can be added to the light emitting layer in order to improve the light emission efficiency or change the light emission wavelength. The dopant can be classified into a fluorescent dopant and a phosphorescent dopant.
• Examples of the fluorescent dopant include anthracene derivatives, perylene derivatives, coumarin derivatives, rubrene derivatives, quinacridone derivatives, squalium derivatives, porphyrin derivatives, styryl dyes, tetracene derivatives, pyrazolone derivatives, decacyclene, phenoxazone, and the like.
• Examples of phosphorescent dopants include iridium complexes.
• the thickness of the light emitting layer can be selected in consideration of the driving voltage and the light emission efficiency, but is usually about 2 to 200 nm.
• a method of applying a solution containing a light emitting material on or above the substrate, a vacuum deposition method, a transfer method, or the like can be used.
• the solvent used for film formation from the solution is the same as described and exemplified in the section of film formation from the solution of the hole transport layer.
• a printing method such as a spin coating method, a dip coating method, an ink jet printing method, a flexographic printing method, a gravure printing method, or a slit coating method can be used.
• a vacuum deposition method can be used.
• Electron transport layer Materials used for the electron transport layer 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 , Diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and its derivatives, polyquinoline and its derivatives, polyquinoxaline and its derivatives, polyfluorene and its derivatives, oxadiazole derivatives, benzoquinone And its derivatives, anthraquinone and its derivatives, metal complexes of 8-hydroxyquinoline and its derivatives, polyquinoline and its derivatives, polyquinoxaline and its derivatives, polyquinoxaline and its derivatives.
• the electron transport layer is formed by a vacuum deposition method from powder or a method by film formation from a solution or a molten state.
• the material used in the above is a polymer compound
• a method by film formation from a solution or a molten state is used.
• a polymer binder may be used in combination.
• Film formation from a solution is similar to the method of forming a hole transport layer from a solution.
• the thickness of the electron transport layer can be adjusted in consideration of the drive voltage and light emission efficiency, but it needs to be thick enough not to generate pinholes. Absent.
• the thickness of the electron transport layer is usually 1 nm to 1 ⁇ m, preferably 2 nm to 500 nm, and more preferably 5 nm to 200 nm.
• Electron injection layer is an electron injection layer having a single layer structure of a Ca layer, or a metal belonging to groups IA and IIA of the periodic table excluding Ca, and having a work function of 1.
• Examples of the metal of group IA of the periodic table having a work function of 1.5 to 3.0 eV or oxides, halides, and carbonates thereof include lithium, lithium fluoride, sodium oxide, lithium oxide, and lithium carbonate.
• the metals of Group IIA of the periodic table excluding Ca having a work function of 1.5 to 3.0 eV or oxides, halides and carbonates thereof include strontium, magnesium oxide, magnesium fluoride, strontium fluoride, fluorine Barium oxide, strontium oxide, magnesium carbonate, and the like.
• the electron injection layer is formed by vapor deposition, sputtering, printing, or the like. The thickness of the electron injection layer is preferably 1 nm to 1 ⁇ m.
• the material of the cathode is preferably a material having a small work function and allowing easy electron injection into the light emitting layer.
• the alloy examples include magnesium-silver alloy, magnesium-indium alloy, magnesium-aluminum alloy, indium-silver alloy, lithium-aluminum alloy, lithium-magnesium alloy, lithium-indium alloy, and calcium-aluminum alloy.
• the cathode has a laminate structure of two or more layers, a laminate structure of a metal, metal oxide, metal fluoride, or an alloy thereof and a metal such as aluminum, silver, or chromium is preferable.
• the thickness of the cathode may be selected in consideration of electric conductivity and durability, and is usually 10 nm to 10 ⁇ m, preferably 20 nm to 1 ⁇ m, and more preferably 50 nm to 500 nm.
• a vacuum deposition method, a sputtering method, a laminating method in which a metal thin film is thermocompression bonded, or the like is used.
• a protective layer for protecting the light emitting element may be attached after the cathode is manufactured. In order to stably use the light emitting element for a long period of time, it is preferable to attach a protective layer and / or a protective cover in order to protect the light emitting element from the outside.
• the protective layer high molecular weight compounds, metal oxides, metal fluorides, metal borides and the like can be used.
• the protective cover a metal plate, a glass plate, a plastic plate having a surface subjected to low water permeability treatment, or the like can be used.
• the protection method include a method in which the protective cover is bonded to the element substrate with a thermosetting resin or a photocurable resin and sealed. If a space is maintained using a spacer, it is easy to prevent damage to the element. If an inert gas such as nitrogen or argon is sealed in the space, oxidation of the cathode can be prevented, and moisture adsorbed in the manufacturing process can be obtained by installing a desiccant such as barium oxide in the space. Or it becomes easy to suppress that the trace amount water
• the light-emitting element of the present invention can be used as a planar light source, a display device such as a segment display device or a dot matrix display device, a backlight of a liquid crystal display device, or the like.
• a planar light source such as a segment display device or a dot matrix display device, a backlight of a liquid crystal display device, or the like.
• the planar anode and cathode are arranged so as to overlap each other.
• pattern-like light emission a method in which a mask having a pattern-like window is provided on the surface of a planar light-emitting element, an organic layer of a non-light-emitting portion is formed to be extremely thick and substantially non-light-emitting.
• both the anode and the cathode are formed in a stripe shape and arranged so as to be orthogonal to each other. Partial color display and multicolor display are possible by a method of separately coating a plurality of types of polymer compounds having different emission colors or a method using a color filter or a fluorescence conversion filter.
• the dot matrix element can be driven passively, or may be actively driven in combination with a TFT or the like.
• These display elements can be used as display devices for computers, televisions, mobile terminals, mobile phones, car navigation systems, video camera viewfinders, and the like.
• the planar light-emitting element is a self-luminous thin type, and can be suitably used as a planar light source for backlights of liquid crystal display devices, planar light sources for illumination, and the like. If a flexible substrate is used, it can also be used as a curved light source or display device.
• TSKgel SuperHM-H manufactured by Tosoh
• TSKgel SuperH2000 manufactured by Tosoh
• a differential refractive index detector manufactured by Shimadzu Corporation, trade name: RID-10A
• HPLC High performance liquid chromatography
• the HPLC area percentage value which is an index of the purity of the compound, was determined by high performance liquid chromatography (manufactured by Shimadzu Corporation, trade name: LC-20A) at 254 nm unless otherwise specified.
• the compound to be measured was dissolved in tetrahydrofuran or chloroform to a concentration of 0.01 to 0.2% by weight, and 1 to 10 ⁇ L was injected into HPLC depending on the concentration.
• Kaseisorb LC ODS 2000 manufactured by Tokyo Chemical Industry Co., Ltd.
• the detector As the detector, a photodiode array detector (manufactured by Shimadzu Corporation, trade name: SPD-M20A) was used. (Glass-transition temperature) In the examples, the glass transition temperature (Tg) was determined by a differential scanning calorimeter (DSC, manufactured by TA Instruments, trade name: DSC2920). As measurement conditions, the sample was held at 200 ° C. for 5 minutes, then rapidly cooled to ⁇ 50 ° C. and held for 30 minutes. After raising the temperature to 30 ° C., the measurement was carried out to 300 ° C. at a temperature rising rate of 5 ° C. per minute.
• DSC differential scanning calorimeter
• the fluorescence characteristics were evaluated by the following methods.
• the polymer compound was dissolved in xylene (manufactured by Kanto Chemical Co., Inc., grade for electronic industry). At this time, the solid content was adjusted to 0.8% by weight, and the solution was spin-coated on a quartz plate at a rotational speed of 1500 rpm to prepare a polymer compound thin film. This thin film was excited at a wavelength of 350 nm, and a fluorescence spectrum was measured using a fluorescence spectrophotometer (manufactured by JOBINYVON-SPEX, trade name: Fluorolog).
• photoluminescence quantum yield measurement is performed using an absolute PL quantum yield measurement apparatus (trade name: C9920-02, manufactured by Hamamatsu Photonics), an excitation center wavelength of 325 nm, an excitation wavelength range of 315 to 335 nm, and a measurement wavelength range. Measurement was performed at 390 to 800 nm.
• the temperature of the reaction solution was raised to room temperature, and then the organic layer was dried using sodium sulfate and concentrated under reduced pressure.
• the obtained oil toluene 500 ml was added and washed with water (100 ml ⁇ 3), and then the organic layer was dried using sodium sulfate and concentrated under reduced pressure.
• the Grignard reagent was synthesized by further refluxing for 1 hour. 2,7-Dibromofluorenone (23.7 g, 70 mmol) and diethyl ether (300 ml) were mixed in another 500 ml four-neck flask purged with argon, and the previously synthesized Grignard reagent was added at room temperature over 30 minutes. And dripped. After completion of the dropwise addition, the mixture was refluxed for 4 hours. After completion of the reaction, the reaction mixture was quenched by adding 100 ml of water, and washed with water (200 ml ⁇ 3) using a separatory funnel. The obtained organic layer was dried over sodium sulfate and then concentrated under reduced pressure.
• chloroform 50 ml was added, washed twice with a 10 wt% aqueous sodium carbonate solution (50 ml), dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized (chloroform-acetone).
• Activated carbon (3 g) was added to a solution obtained by heating and dissolving the obtained solid in methylene chloride (330 g), and the mixture was stirred for 1 hour at room temperature.
• Activated carbon was removed with a filter pre-coated with silica gel, and acetone was slowly added to the obtained solution to crystallize it, followed by drying under reduced pressure.
• Aqueous solution (8.2 ml, 6.8 mmol) was added and reacted for 20 hours under reflux. After cooling once, a solution of phenylboric acid (0.02 g, 0.15 mmol) suspended in 1 ml of toluene was added, and the mixture was further reacted for 2 hours under reflux. After diluting with toluene (20 ml), the aqueous layer was removed, 9 wt% aqueous sodium N, N-diethyldithiocarbamate (9 ml) was added, and the mixture was stirred at 90 ° C. for 2 hours.
• the obtained solution was slowly added to methanol (250 ml) while stirring, and further stirred for 30 minutes to precipitate a polymer.
• the polymer was collected by suction filtration, washed with methanol (50 ml), and dried under reduced pressure to obtain polymer compound P1 as a polymer (1.20 g, yield 80%).
• the number average molecular weight Mn in terms of polystyrene of the polymer compound P1 is 1.2 ⁇ 10 5
• the polystyrene equivalent weight average molecular weight Mw is 3.8 ⁇ 10 5
• the glass transition temperature was 108 ° C., and the fluorescence peak wavelengths of the thin film were 422 nm and 446 nm.
• the polymer compound P1 was assumed to comprise the following repeating units at the following ratio (molar ratio).
• ratio molar ratio
• Example 4> Synthesis of polymer compound P2) 2,7-bis (1,3,2-dioxaborolan-2-yl) -9,9-dioctylfluorene (0.4223 g, 0.796 mmol), 2,7-dibromo-9,9-dioctylfluorene (0.
• Aqueous solution (2.2 ml, 3.6 mmol) was added and reacted under reflux for 20 hours. After cooling once, a solution in which phenylboric acid (0.10 g, 0.8 mmol) was suspended in 3 ml of toluene was added, and the mixture was further reacted for 2 hours under reflux. After diluting with toluene (20 ml), the aqueous layer was removed, and a 9 wt% sodium N, N-diethyldithiocarbamate aqueous solution (5 ml) was added, and the mixture was stirred at 90 ° C. for 2 hours.
• the obtained solution was slowly added to methanol (125 ml) while stirring, and further stirred for 30 minutes to precipitate a polymer.
• the product was collected by suction filtration, washed with methanol (25 ml), and dried under reduced pressure to obtain a polymer compound P1 as a polymer (0.50 g, yield 78%).
• the number average molecular weight Mn in terms of polystyrene of the polymer compound P2 is 1.1 ⁇ 10 5
• the polystyrene equivalent weight average molecular weight Mw is 2.4 ⁇ 10. 5
• the glass transition temperature was 86 ° C., and the fluorescence peak wavelengths of the thin film were 422 nm and 440 nm.
• the polymer compound P2 was assumed to comprise the following repeating units at the following ratio (molar ratio).
• ratio molar ratio
• Example 5> Synthesis of polymer compound P3) 2,7-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9,9-bis (4′-hexylphenyl) fluorene (0.5909 g, 0. 800 mmol), 2,7-dibromo-9,9-bis (4′-hexylphenyl) fluorene (0.4125 g, 0.640 mmol), compound M1 (0.2308 g, 0.136 mmol), and compound M2 (0.
• the obtained solution was slowly added to methanol (125 ml) while stirring, and further stirred for 30 minutes to precipitate a polymer.
• the product was collected by suction filtration, washed with methanol (25 ml), and dried under reduced pressure to obtain polymer compound P1 as a polymer (0.72 g, yield 76%).
• the number average molecular weight Mn in terms of polystyrene of the polymer compound P3 is 1.4 ⁇ 10 5
• the polystyrene equivalent weight average molecular weight Mw is 3.9 ⁇ 10 5
• the glass transition temperature was 179 ° C., and the fluorescence peak wavelength of the thin film was 448 nm.
• the polymer compound P3 was assumed to comprise the following repeating units at the following ratio (molar ratio).
• ⁇ Comparative Example 4> Synthesis of Polymer Compound CP1) 2,7-bis (1,3,2-dioxaborolan-2-yl) -9,9-dioctylfluorene (1.0675 g, 2.012 mmol), 2,7-dibromo-9,9-dioctylfluorene (0.
• Aqueous solution (5.5 ml, 9.1 mmol) was added and reacted for 7 hours under reflux. After cooling, a solution in which phenylboric acid (0.25 g, 2.02 mmol) was suspended in 3 ml of toluene was added, and the mixture was further reacted for 2 hours under reflux. After diluting with toluene (20 ml), the aqueous layer was removed, and a 9 wt% sodium N, N-diethyldithiocarbamate aqueous solution (12 ml) was added, and the mixture was stirred at 90 ° C. for 2 hours.
• the obtained solution was slowly added to methanol (320 mL) while stirring, and further stirred for 30 minutes to precipitate a polymer.
• the product was collected by suction filtration, washed with methanol (60 ml), and dried under reduced pressure to obtain polymer compound CP1 (1.22 g, yield 76%) as a polymer.
• the number average molecular weight Mn in terms of polystyrene of the polymer compound CP1 is 1.7 ⁇ 10. 5
• the polystyrene equivalent weight average molecular weight Mw is 5.8 ⁇ 10 5
• the glass transition temperature was 83 ° C., and the fluorescence peak wavelengths of the thin film were 422 nm and 438 nm.
• the polymer compound CP1 was assumed to comprise the following repeating units at the following ratio (molar ratio).
• ⁇ Comparative Example 5> Synthesis of Polymer Compound CP2) 2,7-bis (1,3,2-dioxaborolan-2-yl) -9,9-dioctylfluorene (1.1814 g, 2.228 mmol), 2,7-dibromo-9,9-dioctylfluorene (0.
• Aqueous solution (7.3 ml, 10.4 mmol) was added and reacted under reflux for 7 hours. After cooling, a solution in which phenylboric acid (0.27 g, 2.25 mmol) was suspended in 3 ml of toluene was added, and the mixture was further reacted for 2 hours under reflux. After diluting with toluene (22 ml), the aqueous layer was removed, and a 9 wt% aqueous sodium N, N-diethyldithiocarbamate solution (14 ml) was added, and the mixture was stirred at 90 ° C. for 2 hours.
• the obtained solution was slowly added to methanol (350 ml) while stirring, and further stirred for 30 minutes to precipitate a polymer.
• the product was collected by suction filtration, washed with methanol (70 ml), and dried under reduced pressure to obtain a polymer compound CP2 as a polymer (1.65 g, yield 88%).
• the number average molecular weight Mn in terms of polystyrene of the polymer compound CP2 is 2.8 ⁇ 10 4
• the polystyrene equivalent weight average molecular weight Mw is 6.1 ⁇ 10 4
• the glass transition temperature was 89 ° C., and the fluorescence peak wavelengths of the thin film were 423 nm and 438 nm.
• the polymer compound CP2 was assumed to comprise the following repeating units at the following ratio (molar ratio).
• ⁇ Comparative Example 6> Synthesis of Polymer Compound CP3) 2,7-bis (1,3,2-dioxaborolan-2-yl) -9,9-dioctylfluorene (0.7838 g, 1.478 mmol), 2,7-dibromo-9,9-dioctylfluorene (0. 6581 g, 1.200 mmol) and compound CM3 (0.2267 g, 0.300 mmol) were dissolved in toluene (17 ml) under an argon gas atmosphere.
• the aqueous layer was removed, an aqueous 9 wt% sodium N, N-diethyldithiocarbamate solution (10 ml) was added, and the mixture was stirred at 90 ° C. for 2 hours.
• the organic layer was washed twice with ion-exchanged water (20 ml) and 3 wt%. This was washed twice with an aqueous acetic acid solution (20 ml) and twice with ion-exchanged water (20 ml), then dropped into methanol (250 ml) and stirred for 30 minutes to precipitate a polymer.
• the polymer was collected by suction filtration, washed with methanol (50 ml), and dried under reduced pressure to obtain a crude polymer (0.94 g).
• This crude polymer was dissolved in toluene (50 ml), passed through alumina (5.5 g) and silica gel (16.5 g) packed in a column, and further toluene (72 ml) was passed through.
• the obtained solution was slowly added while stirring methanol (250 ml), and further stirred for 30 minutes to precipitate a polymer.
• the polymer was collected by suction filtration, washed with methanol (50 ml), and dried under reduced pressure to obtain polymer compound CP3 (0.83 g, yield 69%) as a polymer.
• the number average molecular weight Mn in terms of polystyrene of the polymer compound CP3 is 1.7 ⁇ 10 4
• the polystyrene equivalent weight average molecular weight Mw is 3.2 ⁇ 10 4
• the glass transition temperature was 73 ° C.
• the fluorescence peak wavelengths of the thin film were 423 nm and 446 nm.
• the polymer compound CP3 was assumed to comprise the following repeating units at the following ratio (molar ratio).
• Example 6> (Production of light-emitting element P1)
• the polymer compound P1 was dissolved in xylene (manufactured by Kanto Chemical Co., Inc., grade for electronic industry).
• the solid content was adjusted to 1.2% by weight.
• a solution of poly (3,4-ethylenedioxythiophene) / polystyrenesulfonic acid (trade name: BaytronP CH8000) on a glass substrate with an ITO film having a thickness of 150 nm formed by sputtering.
• a film having a thickness of 65 nm was formed and dried on a hot plate at 200 ° C. for 10 minutes.
• a film was formed at a rotational speed of 850 rpm by spin coating using the prepared xylene solution. The film thickness was about 100 nm. This was dried at 130 ° C.
• the element configuration is ITO / BaytronP (65 nm) / polymer compound P1 / LiF / Ca / Al.
• the degree of vacuum is 1 ⁇ 10 -4 After reaching Pa or less, metal deposition was started.
• voltage was applied to the light emitting device P1, deep blue light emission with a peak wavelength (EL) of 450 nm derived from the polymer compound P1 was exhibited.
• EL peak wavelength
• the maximum luminous efficiency was 1.9 cd / A, the voltage at that time was 3.6 V, and the external quantum yield was 1.5%.
• Example 7 (Production of light-emitting element P2)
• a 1.3 wt% xylene solution of the polymer compound P2 was used instead of the 1.2 wt% xylene solution of the polymer compound P1, and the spin coat rotation speed was changed to 1000 rpm.
• the film thickness was about 100 nm.
• the maximum luminous efficiency was 0.82 cd / A, the voltage at that time was 6.4 V, and the external quantum yield was 0.92%.
• Example 8 (Production of light-emitting element P3)
• a 1.2 wt% xylene solution of the polymer compound P3 was used, and the rotation speed of the spin coat was changed to 1000 rpm. Produced a light emitting device P3 in the same manner as in Example 6.
• the film thickness was about 100 nm.
• blue light emission with a peak wavelength (EL) of 455 nm derived from the polymer compound P3 was observed.
• the maximum luminous efficiency was 2.8 cd / A
• the voltage at that time was 4.6 V
• the external quantum yield was 2.0%.
• the voltage at 9.2 is 9.2 V
• the chromaticity coordinates C.I. I. E. 1931 (0.15, 0.17)
• the light emission efficiency was 2.1 cd / A
• the external quantum yield was 1.6%.
• Example 7 (Production of Light-Emitting Element CP1)
• a 1.2 wt% xylene solution of the polymer compound CP1 was used instead of the 1.2 wt% xylene solution of the polymer compound P1, and the spin coat rotation speed was changed to 2000 rpm.
• the film thickness was about 100 nm.
• the maximum luminous efficiency was 1.5 cd / A, the voltage at that time was 3.2 V, and the external quantum yield was 1.2%.
• the film thickness was about 100 nm.
• EL peak wavelength
• the maximum luminous efficiency was 0.18 cd / A
• the voltage at that time was 5.6 V
• the external quantum yield was 0.29%.
• the voltage at 7.8V is 7.8V
• the light emission efficiency was 0.34 cd / A
• the external quantum yield was 0.37%.
• Example 9 (Production of Light-Emitting Element CP3)
• a 1.8 wt% xylene solution of the polymer compound CP2 was used instead of the 1.2 wt% xylene solution of the polymer compound P1, and the spin coat rotation speed was changed to 2200 rpm.
• the film thickness was about 100 nm.
• blue light emission with a peak wavelength (EL) of 450 nm derived from the polymer compound CP1 was exhibited.
• EL peak wavelength
• Example 9 instead of the 0.8% by weight xylene solution of the polymer compound P1, the polymer compound P1 has the following formula:
• a 0.8 wt% xylene solution of a mixture to which 5 wt% of a light emitting material EM-C (trade name: ADS077RE), represented by The photoluminescence quantum rate was measured.
• the quantum yield was 24%
• EM-D Tokyo Chemical Industry Co., Ltd., 5,6,11,12-tetraphenylnaphthacene
• the polymer compound of the present invention has 1000 cd / m. 2 It is a polymer compound useful for the production of a light-emitting device having an excellent external quantum yield at a high luminance.
• the luminescent chromaticity can be easily adjusted by using the polymer compound of the present invention as a composition with the luminescent material.
• the polymer compound of the present invention is a polymer compound useful for the production of a light-emitting element having an excellent external quantum yield at a luminance of 1000 cd / m 2 . Furthermore, the luminescent chromaticity can be easily adjusted by using the polymer compound of the present invention as a composition with a luminescent material.

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