US20030168656A1 - New polymer and polymer light-emitting device using the same - Google Patents

New polymer and polymer light-emitting device using the same Download PDF

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US20030168656A1
US20030168656A1 US10/309,101 US30910102A US2003168656A1 US 20030168656 A1 US20030168656 A1 US 20030168656A1 US 30910102 A US30910102 A US 30910102A US 2003168656 A1 US2003168656 A1 US 2003168656A1
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formula
polymer
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Satoshi Kobayashi
Takanobu Noguchi
Yoshiaki Tsubata
Makoto Kitano
Shuji Doi
Takahiro Ueoka
Akiko Nakazono
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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Assigned to SUMITOMO CHEMICAL COMPANY, LIMITED reassignment SUMITOMO CHEMICAL COMPANY, LIMITED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: NAKAZONO, AKIKO, DOI, SHUJI, KITANO, MAKOTO, KOBAYASHI, SATOSHI, NOGUCHI, TAKANOBU, TSUBATA, YOSHIAKI, UEOKA, TAKAHIRO
Publication of US20030168656A1 publication Critical patent/US20030168656A1/en
Priority to US10/954,223 priority Critical patent/US7662478B2/en
Priority to US11/955,788 priority patent/US20080103278A1/en
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Definitions

  • the present invention relates to a new polymer, a process for producing the same, a polymeric fluorescent substance thereof, and a polymer light-emitting device (hereinafter, may be referred to as “polymer LED”) using the same.
  • High molecular weight light-emitting materials and high molecular weight charge transporting materials are variously studied since they are soluble in solvents, unlike low molecular weight materials, and can be formed into light emitting layers or charge transporting layers by coating method.
  • polyfluorene derivatives are known.
  • the object of the present invention is to provide a new polymer which can be used as a light-emitting material, a charge transporting material, etc., a process for producing the same, and a polymer light-emitting device using said polymer.
  • the present invention relates to a polymer having a polystyrene reduced number average molecular weight of 10 3 -10 8 , and comprising a repeating unit represented by the below formula (1),
  • a 1 is a divalent group represented by -Z- or -Z-Z- in which Z is an atomic group which may have a substituent;
  • a 1 represents a divalent group in which the bond distance ratio (bond distance C2-A 1 /bond distance C2-C1) is 1.10 or more, in which C2 is the carbon of ⁇ position, and C1 is the carbon of ⁇ position, respectively to A 1 ;
  • R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 each independently represent a hydrogen atom, a halogen atom, an alkyl group, alkenyl group, alkynyl group, alkyloxy group, alkylthio group, an alkylamino group, aryl group, aryloxy group, arylthio group, arylamino group, arylalkyl group, arylalkyloxy group, aryl alkylthio group, arylalkylamino group, substituted si
  • a hetero atom is preferable, and as the hetero atom, Si, P, S, Ge, Sn, Se and Te are exemplified.
  • R each independently represents a hydrogen atom, a halogen atom, an alkyl group, alkyloxy group, alkylthio group, alkylamino group, aryl group, aryloxy group, arylthio group, arylamino group, arylalkyl group, arylalkyloxy group, arylalkylthio group, arylalkylamino group, substituted silyl group, acyl group, acyloxy group, imino group, amide group, arylalkenyl group, arylalkynyl group, monovalent heterocyclic group, or cyano group.
  • the bond-distance ratio in the above formula (1) is computable by optimizing the molecular structure of a compound using quantum-chemistry calculation.
  • quantum-chemistry calculation method semi-empirical and non-empirical molecular orbital methods, and a density functional method, etc. can be used.
  • a density functional method included in quantum-chemistry calculation program Gaussian 98 a structure-optimizing calculation of a compound can be performed using 6-31 g* as a basis function, and b3lyp as a density functional approximation, and the bond-distance ratio can be determined. (Ref: J. Chem. Phys., 98, 5648(1993)).
  • the bond distance C2-A 1 is the distance from C2 to the atom of the group A 1 to which C2 is directly bonded.
  • both bond distance ratios are 1.10 or more.
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 in the above formula (1) each independently represent a hydrogen atom, a halogen atom, an alkyl group, alkenyl group, alkynyl group, alkyloxy group, alkylthio group, alkylamino group, aryl group, aryloxy group, arylthio group, arylamino group, arylalkyl group, arylalkyloxy group, arylalkylthio group, arylalkylamino group, substituted silyl group, acyl group, acyloxy group, imino group, amide group, arylalkenyl group, arylalkynyl group, monovalent heterocyclic group, or cyano group.
  • R 2 and R 3 may be connected to form a ring; and R 4 and R 5 may be connected to form a ring.
  • halogen atom exemplified are fluorine, chlorine, bromine, and iodine.
  • the alkyl group may be any of linear, branched or cyclic, and usually has about 1 to 20 carbon atoms, and the group may have a substituent.
  • exemplified are: a methyl group, ethyl group, propyl group, i-propyl group, butyl, i-butyl, t-butyl, pentyl group, hexyl group, cyclohexyl group, heptyl group, octyl group, 2-ethyl hexyl group, nonyl group, decyl group, 3,7-dimethyloctyl group, lauryl group, trifluoromethyl group, pentafluoroethyl group, perfluorobutyl, perfluoro hexyl group, perfluorooctyl group, etc.; and preferably pentyl group, hexyl group, octyl group, 2-e
  • the alkenyl group may be any of linear, branched or cyclic, and usually has about 2 to 20 carbon atoms, and the group may have a substituent. Specifically, exemplified are: ethenyl group, propenyl group, 2-propenyl group, 1-methyl propenyl group, 2-methylpropenyl group, 1,2-dimethyl propenyl group, butenyl group, 2-methylbutenyl group, 1,3-butadienyl group, pentenyl group, hexenyl group, cyclohexenyl group, heptenyl group, octenyl group, 2-ethyl hexenyl group, trifluoroethenyl group, perfluorobutenyl group, perfluorohexenyl group, perfluorooctenyl group, etc.
  • the alkynyl group may be any of linear, branched or cyclic, and usually has about 2 to 20 carbon atoms, and the group may have a substituent.
  • exemplified are: ethynyl group, propynyl group, 2-propynyl group, 2-methyl propynyl group, butynyl group, 2-methylbutynyl group, 1,3-butanediyl group, pentynyl group, hexynyl group, cyclohexynyl group, heptynyl group, octynyl group, 2-ethyl hexynyl group, fluoroethynyl group, perfluorobutynyl group, perfluorohexynyl group, perfluorooctynyl group, etc.
  • the alkylthio group may be any of linear, branched or cyclic, and usually has about 1 to 40 carbon atoms, and the group may be monoalkylamino group or dialkylamino group. Specifically, exemplified are: methylamino group, dimethyl amino group, ethylamino group, diethylamino group, propyl amino group, dipropylamino group, i-propylamino group, diisopropyl amino group, butylamino group, i-butylamino group, t-butylamino group, pentylamino group, hexylamino group, cyclohexylamino group, heptylamino group, octyl amino group, 2-ethylhexylamino group, nonylamino group, decylamino group, 3,7-dimethyloctylamino group, laurylamino group, cycl
  • the aryl group may have a substituent, and usually has about 6 to 60 carbon atoms.
  • exemplified are: phenyl group, C 1 -C 12 alkoxyphenyl group (C 1 -C 12 shows 1-12 carbon atoms), C 1 -C 12 alkylphenyl group, 1-naphthyl group, 2-naphthyl group, pentafluorophenyl group, etc., and preferably C 1 -C 12 alkoxyphenyl group, and C 1 -C 12 alkylphenyl group.
  • the aryloxy group may have a substituent on the aromatic ring, and usually has about 6 to 60 carbon atoms.
  • exemplified are: phenoxy group, C 1 -C 12 alkoxyphenoxy group, C 1 -C 12 alkylphenoxy group, 1-naphtyloxy group, 2-naphtyloxy group, pentafluorophenyloxy group, pyridyloxy group, pyridazinyloxy group, pyrimidyloxy group, pyrazyloxy group, triazinyloxy group, etc.; and preferably C 1 -C 12 alkoxyphenoxy group, and C 1 -C 12 alkyl phenoxy group.
  • the arylamino group may have a substituent on the aromatic ring, and usually has about 6 to 60 carbon atoms.
  • exemplified are: phenylamino group, diphenyl amino group, C 1 -C 12 alkoxyphenylamino group, di(C 1 -C 12 alkoxyphenyl)amino group, di(C 1 -C 12 alkylphenyl)amino group, 1-naphtylamino group, 2-naphtylamino group, pentafluorophenylamino group, pyridylamino group, pyridazinylamino group, pyrimidylamino group, pyrazylamino group, triazinylamino group etc.; and preferably C 1 -C 12 alkylphenylamino group, and di(C 1 -C 12 alkylphenyl)amino group.
  • the arylalkyloxy group may have a substituent, and usually has about 7 to 60 carbon atoms.
  • exemplified are: phenyl-C 1 -C 12 alkyloxy group, C 1 -C 12 alkyloxy phenyl-C 1 -C 12 alkyloxy group, C 1 -C 12 alkylphenyl-C 1 -C 12 alkyloxy group, 1-naphtyl-C 1 -C 12 alkyloxy group, 2-naphtyl-C 1 -C 12 alkyloxy group, etc.; and preferably C 1 -C 12 alkyloxy phenyl-C 1 -C 12 alkyloxy group, and C 1 -C 12 alkylphenyl-C 1 -C 12 alkyloxy group.
  • the arylalkylthio group may have a substituent, and usually has about 7 to 60 carbon atoms.
  • exemplified are: phenyl-C 1 -C 12 alkylthio group, C 1 -C 12 alkyloxy phenyl-C 1 -C 12 alkylthio group, C 1 -C 12 alkylphenyl-C 1 -C 12 alkylthio group, 1-naphtyl-C 1 -C 12 alkylthio group, 2-naphtyl-C 1 -C 12 alkylthio group, etc.; and preferably C 1 -C 12 alkyloxy phenyl-C 1 -C 12 alkylthio group, and C 1 -C 12 alkylphenyl-C 1 -C 12 alkylthio group.
  • the arylalkylamino group usually has about 7 to 60 carbon atoms.
  • exemplified are: phenyl-C 1 -C 12 alkyl amino group, C 1 -C 12 alkoxyphenyl-C 1 -C 12 alkylamino group, C 1 -C 12 alkylphenyl-C 1 -C 12 alkylamino group, di(C 1 -C 12 alkoxy phenyl-C 1 -C 12 alkyl)amino group, di(C 1 -C 12 alkylphenyl-C 1 -C 12 alkyl)amino group, 1-naphtyl-C 1 -C 12 alkylamino group, 2-naphtyl-C 1 -C 12 alkylamino group, etc.; and preferably C 1 -C 12 alkylphenyl-C 1 -C 12 alkylamino group, and di(C 1 -C 12 alkylpheny
  • substituted silyl group specifically exemplified are: trialkylsilyl groups, such as trimethylsilyl group, triethylsilyl group, tripropylsilyl group, tri-1-propylsilyl group, dimethyl-1-propylsilyl group, diethyl-1-propylsilyl group, t-butyldimethylsilyl group, pentyldimethylsilyl group, hexyldimethylsilyl group, heptyldimethyl silyl group, octyldimethylsilyl group, 2-ethylhexyldimethylsilyl group, nonyldimethylsilyl group, decyldimethylsilyl group, 3,7-dimethyloctyl-dimethylsilyl group, and lauryldimethylsilyl group, and the like; triarylsilyl groups, such as triphenyl silyl group,
  • the acyl group has usually 2 to 20 carbon atoms, and specifically exemplified are acetyl group, propionyl group, butyryl group, isobutyryl group, pivaloyl group, benzoyl group, trifluoroacetyl group, pentafluorobenzoyl group, etc.
  • the acyloxy group usually has 2 to 20 carbon atoms, and specifically exemplified are acetyloxy group, propionyloxy group, butyryloxy group, isobutyryloxy group, pivaloyloxy group, benzoyloxy group, trifluoroacetyloxy group, pentafluorobenzoyloxy group, etc.
  • the arylalkenyl group usually has 7 to 60 carbon atoms, and specifically exemplified are phenyl-C 2 -C 12 alkenyl group, C 1 -C 12 alkyloxyphenyl-C 2 -C 12 alkenyl group, C 1 -C 12 alkyl phenyl-C 2 -C 12 alkenyl group, 1-naphtyl-C 2 -C 12 alkenyl group, 2-naphtyl-C 2 -C 12 alkenyl group, etc.; and preferably C 1 -C 12 alkyloxy phenyl-C 2 -C 12 alkenyl group, and C 1 -C 12 alkyl phenyl-C 2 -C 12 alkenyl group.
  • the arylalkynyl group usually has 7 to 60 carbon atoms, and specifically exemplified are phenyl-C 2 -C 12 alkynyl group, C 1 -C 12 alkyloxyphenyl-C 2 -C 12 alkynyl group, C 1 -C 12 alkyl phenyl-C 2 -C 12 alkynyl group, 1-naphtyl-C 2 -C 12 alkynyl group, 2-naphtyl-C 2 -C 12 alkynyl group, etc.; and preferably C 1 -C 12 alkyloxyphenyl-C 2 -C 12 alkynyl group, and C 1 -C 12 alkylphenyl-C 2 -C 12 alkynyl group.
  • the monovalent heterocyclic group means an atomic group in which a hydrogen atom is removed from a heterocyclic compound, and usually has about 4 to 60 carbon atoms.
  • thienyl group C 1 -C 12 alkyl thienyl group pyroryl group, furyl group, pyridyl group, C 1 -C 12 alkylpyridyl group, etc.
  • thienyl group C 1 -C 12 alkylthienyl group
  • pyridyl group C 1 -C 12 alkylpyridyl group, etc.
  • thienyl group C 1 -C 12 alkylthienyl group, pyridyl group, and C 1 -C 12 alkylpyridyl group.
  • a 1 in the above formula (1) is preferably a divalent group represented by the below formula (4), (5), or (6).
  • R 7 represents an alkyl group, alkyloxy group, alkylthio group, alkylamino group, aryl group, aryloxy group, arylthio group, arylamino group, arylalkyl group, arylalkyloxy group, arylalkylthio group, arylalkylamino group, acyl group, acyloxy group, amide group, or monovalent heterocyclic group.
  • a 2 represents Si, Ge, or Sn.
  • R 8 and R 9 each independently represent alkyl group, alkyloxy group, alkylthio group, alkylamino group, aryl group, aryloxy group, arylthio group, arylamino group, arylalkyl group, arylalkyloxy group, arylalkylthio group, arylalkylamino group, acyloxy group, amide group, or monovalent heterocyclic group.
  • l represents 1 or 2.
  • a polymer whose A 1 is a divalent group represented by the above formula (4) a polymer whose A 1 is a divalent group represented by the above formula (5); a polymer whose A 1 is a divalent group represented by formula (6), A 2 is Si, and l is 1; and a polymer whose A 1 is a divalent group represented by formula (6), A 2 is Si, and l is 2.
  • the polymer of the present invention may contain a repeating unit other than the repeating unit represented by the above formula (1).
  • a repeating unit other than formula (1) exemplified are a repeating unit represented by the below formula (7), and a repeating unit represented by formula (8)after-mentioned.
  • Ar 6 represents an arylene group or a divalent heterocyclic group
  • R 17 and R 18 each independently represent a hydrogen atom, an alkyl group, aryl group, monovalent heterocyclic group, or cyano group
  • n represents 0 or 1.
  • the repeating unit represented by the after-mentioned formula (8) is preferable.
  • the Ar 6 may have a substituent, such as an alkyl group, alkyloxy group, alkylthio group, alkylamino group, aryl group, aryloxy group, arylthio group, arylamino group, arylalkyl group, arylalkyloxy group, arylalkylthio group, arylalkylamino group, substituted silyl group, acyl group, acyloxy group, imino group, amide group, imide group, arylalkenyl group, arylalkynyl group, monovalent heterocyclic group, or cyano group. Specific examples of these substituents represent the same as aforementioned. When Ar 6 has a plurality of substituents, they may be mutually the same or different.
  • the arylene group in the present invention includes those containing a benzene ring, a condensed ring, and two or more of independent benzene rings or condensed rings bonded through a group such as a direct bond, a vinylene group or the like.
  • the arylene group has usually 6 to 60 carbon atoms, preferably 6 to 20 carbon atoms.
  • arylene group exemplified are phenylene group (for example, following formula (26)), naphthalenediyl group (following formula (27)), anthracenylene group (following formula (28)), biphenylene group (following formula (29)), triphenylene group (following formula (30)), condensed ring compound group (following formula (31)), etc.
  • the divalent heterocyclic group is an atomic group in which two hydrogen atoms are removed from a heterocyclic compound, and usually has 4 to 60 carbon atoms, preferably 4 to 20 carbon atoms. They may have a substituent on the hetero-ring and the carbon atoms of the substituent are not counted as the carbon atoms of the heterocyclic group.
  • the heterocyclic compound means an organic compound having a cyclic structure in which at least one heteroatom such as oxygen, sulfur, nitrogen, phosphorus, boron, etc. is contained in the cyclic structure as the element other than carbon atoms.
  • Divalent heterocyclic compound group containing a nitrogen as a hetero atom pyridine-diyl group (following formula (32)), diaza phenylene group (following formula (33)), quinolinediyl group (following formula (34)), quinoxaline diyl group (following formula (35)), acridine diyl group (following formula (36)), bipyridyl diyl group (following formula (37)), phenanthroline diyl group (following formula (38)), etc.; groups containing a hetero atom, such as silicon, nitrogen, sulfur, selenium, etc. and having a fluorene structure (following formula (39));
  • R′ each independently represents a hydrogen atom, a halogen atom, an alkyl group, alkyloxy group, alkylthio group, alkyl amino group, aryl group, aryloxy group, arylthio group, aryl amino group, arylalkyl group, arylalkyloxy group, aryl alkylthio group, arylalkylamino group, acyloxy group, amide group, arylalkenyl group, arylalkynyl group, monovalent heterocyclic group, or cyano group.
  • R′′ represents a hydrogen atom, an alkyl group, aryl group, arylalkyl group, silyl group, acyl group, or monovalent heterocyclic group.
  • the repeating unit other than the repeating unit represented by the above formula (1) preferably contains a repeating unit represented by the below formula (8), in view of life time of a device.
  • Ar 1 and Ar 2 each independently represent an arylene group or divalent heterocyclic group;
  • R 11 represents an alkyl group, aryl group, monovalent heterocyclic group, a group represented by the below formula (9) or (10);
  • m represents an integer of 1 to 4,
  • Ar 3 represents an arylene group or divalent heterocyclic group
  • R 12 represents a hydrogen atom, an alkyl group, aryl group, monovalent heterocyclic group, or a group represented by the below formula (10);
  • Y 1 represents
  • R 13 and R 14 each independently represent a hydrogen atom, an alkyl group, aryl group, monovalent heterocyclic group, or cyano group; p represents an integer of 0-2),
  • Ar 4 and Ar 5 each independently represent an arylene group or a divalent heterocyclic group;
  • R 15 represents an alkyl group, aryl group, or monovalent heterocyclic group;
  • R 16 represents a hydrogen atom, an alkyl group, aryl group, or monovalent heterocyclic group;
  • q represents an integer of 1 to 4)].
  • arylene group, and divalent heterocyclic group for Ar 1 -Ar 5 in the above formulas (8)-(10) are the same as those aforementioned.
  • alkyl group, aryl group, and monovalent heterocyclic group for R 11 -R 16 in the above formulas (8)-(10) are the same as those aforementioned.
  • the repeating unit represented by the above formula (8) exemplified are the followings which may have a substituent on the benzene ring or heterocyclic ring.
  • a substituent a halogen atom, an alkyl group, alkyloxy group, alkylthio group, alkylamino group, aryl group, aryloxy group, arylthio group, arylamino group, arylalkyl group, arylalkyloxy group, arylalkylthio group, arylalkylamino group, acyl group, acyloxy group, amide group, imino group, silyl group, silyloxy group, silylthio group, silylamino group, monovalent heterocyclic group, arylalkenyl group, arylethynyl group, and cyano group are exemplified.
  • the repeating units contained in the polymer of the present invention may be connected by non-conjugated units, and may have a non-conjugated portion in the repeating units themselves.
  • R is a group selected from the group consisting of a hydrogen atom, alkyl group having 1 to 20 carbon atoms, aryl group having 6 to 60 carbon atoms, and a heterocyclic group having 4 to 60 carbon atoms
  • Ar represents a hydrocarbon group having 6 to 60 carbon atoms.
  • the polymer may also be a random, block or graft copolymer, or a polymer having an intermediate structure thereof, for example, a random copolymer having block property. From the viewpoint for obtaining a polymer having high fluorescent quantum yield, random copolymers having block property and block or graft copolymers are more preferable than complete random copolymers. Further, the polymer have a branched main chain and more than three terminals, and a dendrimer.
  • the end group of polymer may also be protected with a stable group since if a polymerization active group remains intact, there is a possibility of reduction in light emitting property and life-time when the fluorescent substance is made into an device.
  • Those having a conjugated bond continuing to a conjugated structure of the main chain are preferable, and there are exemplified structures connected to an aryl group or heterocyclic compound group via a carbon-carbon bond.
  • substituents of the chemical formula 10 in JP-A No. 9-45478 are exemplified.
  • the polymer has a polystyrene reduced number average molecular weight of 10 3 to 10 8 . Degree of polymerization thereof changes according to the structure of the repeating units or the ratio thereof. From the viewpoint of film-molding property, generally the total number of repeating units are preferably 20 to 10000, more preferably 30 to 10000, and further preferably 50 to 5000.
  • solvents for the polymer there are exemplified chloroform, methylene chloride, dichloroethane, tetrahydrofuran, toluene, xylene, mesitylene, tetralin, decalin, n-butylbenzene and the like.
  • the polymer can be usually dissolved in these solvents in an amount of 0.1 wt % or more, though the amount differs depending on the structure and molecular weight of the polymer.
  • the polymer of the present invention can be manufactured by condensation polymerization, using a compound represented by the below formula (11).
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and A 1 represent the same as those in formula (1); x 1 and x 2 each independently represent a substituent capable of condensation polymerization.
  • substituents capable of condensation polymerization are: a halogen atom, alkyl sulfonate group, aryl sulfonate group, arylalkyl sulfonate group, borate group, sulfonium methyl group, phosphonium methyl group, phosphonate methyl group, monohalogenated-methyl group, boric-acid group, formyl group, cyano group, vinyl group, etc.; and preferably a halogen atom, alkyl sulfonate group, aryl sulfonate group, and arylalkyl sulfonate group.
  • alkyl sulfonate group methane sulfonate group, ethane sulfonate group, trifluoromethane sulfonate group, etc. are exemplified.
  • aryl sulfonate group benzene sulfonate group, p-toluene sulfonate group, etc. are exemplified.
  • aryl sulfonate group benzyl sulfonate group etc. are exemplified.
  • boric-acid ester group groups represented by the below formulas are exemplified.
  • Me shows a methyl group and Et shows an ethyl group.
  • a polymer whose A 1 is a divalent group represented by the above formula (4) can be manufactured by using a compound whose A 1 is a divalent group represented by the above formula (4) in the above formula (11).
  • a polymer whose A 1 is a divalent group represented by the above (5) formula in the above formula (1) can be manufactured, by using a compound whose A 1 is a divalent group represented by the above (5) formula in the above formula (11).
  • a polymer whose A 1 is a divalent group represented by the above (6) formula in the above formula (1), A 2 is Si, and l is 1, can be manufactured by using a compound whose A 1 is a divalent group represented by the above (6) formula in the above formula (11), and A 2 is Si, and l is 1 is used.
  • a polymer whose A 1 is a divalent group, represented by the above (6) formula in the above formula (1), A 2 is Si, and l is 2 can be manufactured by using a compound whose A 1 is a divalent group represented by the above (6) formula in the above formula (11), and A 2 is Si, and l is 2 is used.
  • a method of producing the polymer of the present invention for example, a method described in JP-A No. 5-202355 is exemplified, when a vinylene group is contained in the main chain.
  • a method described in JP-A No. 5-202355 is exemplified, when a vinylene group is contained in the main chain.
  • there are exemplified methods such as polymerization of a compound having a formyl group with a compound having a phosphonium methyl group, or of a compound having a formyl group and a phosphonium methyl group, according to a Wittig reaction, polymerization of a compound having a vinyl group with a compound having a halogen atom, according to a Heck reaction, polycondensation of a compound having two or more halogenated methyl groups, according to a de-hydrohalogenating method, polycondensation of a compound having two or more sulfonium salt groups, according to a
  • a vinylene group is not contained in the main chain
  • a method of polymerization from corresponding monomers by a Suzuki coupling reaction for example, a method of polymerization from corresponding monomers by a Suzuki coupling reaction, a method of polymerization by a Grignard reaction, a method of polymerization using a Ni(O) catalyst, a method of polymerization using an oxidizer such as FeCl 3 and the like, a method of oxidation polymerization electrochemically, a method of decomposition of an intermediate polymer having a suitable releasing group, and the like are exemplified.
  • the polymerization method by a Wittig reaction the polymerization method by a Heck reaction, the polymerization method by a Horner-Wadsworth-Emmons method, the polymerization method by a Knoevenagel reaction, the polymerization method by a Suzuki coupling reaction, the polymerization method by a Grignard reaction and the polymerization method using a Ni(O) catalyst are preferable since structure control is easy in these methods.
  • x 1 and x 2 are each independently a halogen atom, alkyl sulfonate group, aryl sulfonate group or arylalkyl sulfonate group, preferably a halogen atom, using a palladium catalyst or a nickel catalyst.
  • the compound of the above formula (11) used as a raw material monomer, and a monomer, such as the above formula (7-2) or a formula (8-2) are, if necessary, dissolved in an organic solvent, and reacted at a temperature of below the boiling point and above the melting point of the organic solvent, using an alkali or a suitable catalyst, if necessary.
  • a monomer such as the above formula (7-2) or a formula (8-2)
  • an alkali or a suitable catalyst if necessary.
  • known methods can be used, described in “Organic Reactions”, vol. 14, pp. 270 to 490, John Wiley & Sons, Inc., 1965, “Organic Reactions”, vol. 27, pp.
  • the organic solvent used is subjected to a deoxygenation treatment sufficiently and the reaction is progressed under an inert atmosphere, generally for suppressing a side reaction, though the treatment differs depending on compounds and reactions used. Further, it is preferable to conduct a dehydration treatment likewise (however, this is not applicable in the case of a reaction in a two-phase system with water, such as a Suzuki coupling reaction).
  • an alkali or a catalyst is added appropriately. These may be selected according to the reaction. It is preferable that the alkali or catalyst is soluble sufficiently in a solvent used for the reaction.
  • a method of mixing an alkali or catalyst there is exemplified a method of adding a solution of an alkali or catalyst slowly while stirring under an inner atmosphere of argon and nitrogen and the like or a method of slowly adding the reaction solution to a solution of an alkali or catalyst, inversely.
  • [0108] can be prepared by: after metalating the two iodine atoms of the compound below formula (13) selectively,
  • R 7 represents the same as the above; x5 and x6 each independently represents a chlorine atom, a bromine atom, or an iodine atom.
  • the reaction can be carried out under inert atmospheres, such as nitrogen and argon, in the presence of a solvent.
  • a solvent used for reaction, exemplified are: saturated hydrocarbons, such as pentane, hexane, heptane, octane, and cyclohexane; unsaturated hydrocarbons, such as benzene, toluene, xylene, and ethylbenzene; ethers, such as dimethyl ether, diethyl ether, methyl-t-butyl ether, di-t-butyl ether, tetrahydrofuran, tetrahydropyran, and dioxane; and amines, such as trimethylamine, triethylamine, N,N,N′,N′-tetramethylethylenediamine, and pyridine. These may be used as alone or a mixture thereof.
  • the metalating agent methyl lithium, n-butyl lithium, sec-butyl lithium, t-butyl lithium, phenyl lithium, etc. are exemplified.
  • the reaction temperature is usually ⁇ 30° C. or less, and preferably ⁇ 80° C. or less in order to metalate selectively.
  • magnesium salts such as magnesium chloride and a magnesium bromide
  • copper salt such as copper chloride (I), copper chloride (II), copper bromide (I), copper bromide (II), and copper iodide (I)
  • zinc salts such as zinc chloride, and zinc bromide, and zinc iodide
  • magnesium salt is preferable.
  • reaction After the reaction, it can be obtained by a usual post-treatment, for example, quenching with water, then extracting by an organic solvent, and distilling of the solvent.
  • a usual post-treatment for example, quenching with water, then extracting by an organic solvent, and distilling of the solvent.
  • the product When the product is unstable to water, it can be obtained by a method of distilling a solvent after removing inorganic salt by filtration.
  • Isolation and purification of the product can be performed by a method, such as recrystallization, distillation, or fractionation by chromatography.
  • [0119] can be manufactured by: after metalating the two iodine atoms of the compound represented by the above formula (13), and reacting it with sulfur.
  • reaction method it is the same as that of the synthetic process of the compound represented by the above formula (12).
  • reaction with sulfur it may be added as any form of solid, or dissolved or suspended in a solvent.
  • the temperature of the reaction is from ⁇ 100° C. to 30° C., and preferably from ⁇ 80° C. to 0° C.
  • post-treatment of reaction, and the purification method it is also the same as that of the compound represented by the above formula (12).
  • a compound represented by the below formula (20) whose A 1 is a divalent group represented by the above formula (6) in the above formula (11), and A 2 is Si, and l is 2,
  • [0122] can be manufactured by: after metalating the two iodine atoms of the compound represented by the above formula (13), and reacting it with 1,2-dihalogenated disilyl compound represented by the below formula (22),
  • R 8 and R 9 represent the same as the above.
  • x11 and x12 each independently represent a chlorine atom, a bromine atom, or an iodine atom.
  • the compound represented by the below formula (3-2) can be manufactured by reacting it with the dihalogenated compound after metalating the two iodine atoms of the compound represented by the above formula (13) selectively.
  • the method of reaction, post-treatment, and purification method it is the same as those of the compound represented by the above formula (12).
  • R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 represent the same as those in formula (11).
  • x 1 and x 2 are represent the same as those in formula (11).
  • a 3 represents a divalent group selected from
  • R represents the same as aforementioned.
  • [0129] can be manufactured by reacting a compound (dibenzosilole derivative) represented by the below formula (19), with a halogenation reagent, preferably an N-halogeno compound,
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 8 , and R 9 represent the same as those in formula (11).
  • the reaction can be carried out under inert atmosphere such as nitrogen and argon, in the presence of a solvent.
  • the reaction temperature is preferably from ⁇ 80° C. to the boiling point of the solvent.
  • N-halogeno compound N-chloro succinimide, N-chloro phthalic imide, N-chloro diethylamine, N-chloro dibutyl amine, N-chloro cyclohexyl amine, N-bromosuccinimide, N-bromo phthalic-imide, N-bromo ditrifluoromonomethylamine, N-iodo succinimide, N-iodophthalic imide, etc. are exemplified.
  • saturated hydrocarbons such as pentane, hexane, heptane, octane, cyclohexane
  • unsaturated hydrocarbons such as benzene, toluene, ethylbenzene, xylene
  • halogenated saturated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, and bromocyclohexane
  • halogenated unsaturated hydrocarbons such as chlorobenzene, dichlorobenzene, and trichlorobenzene
  • alcohols such as methanol, ethanol, propanol, isopropanol, butanol, t-butyl alcohol
  • alcohols such as methanol, ethanol, propanol, is
  • the base used for reaction exemplified are: lithium hydride, sodium hydride, potassium hydride, methyl lithium, n-butyl lithium, t-butyl lithium, phenyl lithium, lithium diisopropyl amide, lithium hexamethyldisilazide, sodium hexa methyldisilazide, potassium hexamethyl disilazide, etc.
  • reaction After the reaction, it can be obtained by a usual post-treatment, for example, quenching with water, then extracting by an organic solvent, and distilling of the solvent.
  • Isolation and purification of the product can be performed by a method, such as recrystallization, distillation, or fractionation by chromatography.
  • the polymer of the present invention has strong fluorescence, and it can be used as a polymeric fluorescent substance. Moreover, since the luminescence from a thin film is used, polymeric fluorescent substances having fluorescence in the solid state are used preferably. Moreover, the polymer has excellent electronic transporting property, and can be used suitably as a polymer LED material, or a charge transporting material.
  • the polymer of the present invention can be used also as a material for electronic devices, and can be used also as a coloring matter for lasers, a solar-battery material, an organic semiconductor for organic transistors, and a conductive thin-film material.
  • the polymer LED of the present invention has a light-emitting layer between an anode and a cathode, and the polymer-of the present invention is contained in the light-emitting layer.
  • polymer LEDs having an electron transporting layer disposed between a cathode and a light emitting layer there are listed polymer LEDs having an electron transporting layer disposed between a cathode and a light emitting layer, polymer LEDs having a hole transporting layer disposed between an anode and a light emitting layer, polymer LEDs having an electron transporting layer disposed between a cathode and a light emitting layer and having a hole transporting layer disposed between an anode and a light emitting layer.
  • the polymer LED of the present invention there are exemplified: a device having a layer containing a conducting polymer disposed between at least one of the electrodes and a light emitting layer, adjacently to said electrode; and a device having an insulating layer having a thickness of 2 nm or less disposed between at least one of the electrodes and a light emitting layer, adjacently to said electrode.
  • the light emitting layer is a layer having function to emit a light
  • the hole transporting layer is a layer having function to transport a hole
  • the electron transporting layer is a layer having function to transport an electron.
  • the electron transporting layer and the hole transporting layer are generically called a charge transporting layer.
  • the light emitting layer, hole transporting layer and electron transporting layer may also each independently used in two or more layers.
  • charge transporting layers disposed adjacent to an electrode that having function to improve charge injecting efficiency from the electrode and having effect to decrease driving voltage of an device are particularly called sometimes a charge injecting layer (hole injecting layer, electron injecting layer) in general.
  • the above charge injecting layer or insulation layer having a thickness of 2 nm or less may also be provided adjacent to an electrode, and further, for enhancing adherence of the interface, preventing mixing and the like, a thin buffer layer may also be inserted into the interface of a charge transporting layer and light emitting layer.
  • the polymer LED having a charge injecting layer (electron injecting layer, hole injecting layer) provided, there are listed a polymer LED having a charge injecting layer provided adjacent to a cathode and a polymer LED having a charge injecting layer provided adjacent to an anode.
  • the charge injecting layer there are exemplified: layers containing an conducting polymer; layers which are disposed between an anode and a hole transporting layer and contain a material having an ionization potential between the ionization potential of an anode material and the ionization potential of a hole transporting material contained in the hole transporting layer, and the like.
  • the electric conductivity of the conducting polymer is preferably 10 ⁇ 5 S/cm or more and 10 3 S/cm or less, and for decreasing the leak current between light emitting pixels, more preferably 10 ⁇ 5 S/cm or more and 10 2 S/cm or less, further preferably 10 ⁇ 5 S/cm or more and 10 1 S/cm or less.
  • an anion is used for a hole injecting layer and a cation is used for an electron injecting layer.
  • a polystyrene sulfonate ion, alkylbenzene sulfonate ion, camphor sulfonate ion and the like are exemplified
  • a lithium ion, sodium ion, potassium ion, tetrabutyl ammonium ion and the like are exemplified.
  • the thickness of the charge injecting layer is for example, from 1 nm to 100 nm, preferably from 2 nm to 50 nm.
  • Materials used in the charge injecting layer may be selected appropriately according to the relation with the electrode materials and adjacent layers, and there are exemplified conducting polymers such as polyaniline and derivatives thereof, polythiophene and derivatives thereof, polypyrrole and derivatives thereof, poly(phenylene vinylene) and derivatives thereof, poly(thienylene vinylene) and derivatives thereof, polyquinoline and derivatives thereof, polyquinoxaline and derivatives thereof, polymers containing aromatic amine structures in the main chain or the side chain, and the like, and metal phthalocyanine (copper phthalocyanine and the like), carbon and the like.
  • conducting polymers such as polyaniline and derivatives thereof, polythiophene and derivatives thereof, polypyrrole and derivatives thereof, poly(phenylene vinylene) and derivatives thereof, poly(thienylene vinylene) and derivatives thereof, polyquinoline and derivatives thereof, polyquinoxaline and derivatives thereof, polymers containing aromatic amine structures in the main chain or the side chain,
  • the insulation layer having a thickness of 2 nm or less has function to make charge injection easy.
  • metal fluoride, metal oxide, organic insulation materials and the like are listed.
  • polymer LED having an insulation layer having a thickness of 2 nm or less there are listed polymer LEDs having an insulation layer having a thickness of 2 nm or less provided adjacent to a cathode, and polymer LEDs having an insulation layer having a thickness of 2 nm or less provided adjacent to an anode.
  • anode/insulation layer having a thickness of 2 nm or less/hole transporting layer/light emitting layer/insulation layer having a thickness of 2 nm or less/cathode
  • anode/insulation layer having a thickness of 2 nm or less/light emitting layer/electron transporting layer/cathode
  • anode/insulation layer having a thickness of 2 nm or less/hole transporting layer/light emitting layer/electron transporting layer/insulation layer having a thickness of 2 nm or less/cathode
  • a film forming method from a solution there can be used coating methods such as a spin coating method, casting method, micro gravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method, flexo printing method, offset printing method, inkjet printing method and the like.
  • the optimum value differs depending on material used, and may properly be selected so that the driving voltage and the light emitting efficiency become optimum values, and for example, it is from 1 nm to 1 ⁇ m, preferably from 2 nm to 500 nm, further preferably from 5 nm to 200 nm.
  • light emitting materials other than the above polymeric fluorescent substance can also be mixed in a light emitting layer.
  • the light emitting layer containing light emitting materials other than the above polymeric fluorescent substance may also be laminated with a light emitting layer containing the above polymeric fluorescent substance.
  • the light emitting material known materials can be used.
  • a compound having lower molecular weight there can be used, for example, naphthalene derivatives, anthracene or derivatives thereof, perylene or derivatives thereof; dyes such as polymethine dyes, xanthene dyes, coumarine dyes, cyanine dyes; metal complexes of 8-hydroxyquinoline or derivatives thereof, aromatic amine, tetraphenylcyclopentane or derivatives thereof, or tetraphenylbutadiene or derivatives thereof, and the like.
  • the polymer LED of the present invention has a hole transporting layer
  • the hole transporting materials used there are exemplified polyvinylcarbazole or derivatives thereof, polysilane or derivatives thereof, polysiloxane derivatives having an aromatic amine in the side chain or the main chain, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, polyaniline or derivatives thereof, polythiophene or derivatives thereof, polypyrrole or derivatives thereof, poly(p-phenylenevinylene) or derivatives thereof, poly(2,5-thienylenevinylene) or derivatives thereof, or the like.
  • hole transporting material examples include those described in JP-A Nos. 63-70257, 63-175860, 2-135359, 2-135361, 2-209988, 3-37992 and 3-152184.
  • Polyvinylcarbazole or derivatives thereof are obtained, for example, by cation polymerization or radical polymerization from a vinyl monomer.
  • polysiloxane or derivatives thereof those having the structure of the above hole transporting material having lower molecular weight in the side chain or main chain, since the siloxane skeleton structure has poor hole transporting property.
  • siloxane skeleton structure has poor hole transporting property.
  • aromatic amine having hole transporting property in the side chain or main chain.
  • the method for forming a hole transporting layer is not restricted, and in the case of a hole transporting layer having lower molecular weight, a method in which the layer is formed from a mixed solution with a polymer binder is exemplified. In the case of a polymer hole transporting material, a method in which the layer is formed from a solution is exemplified.
  • the solvent used for the film forming from a solution is not particularly restricted providing it can dissolve a hole transporting material.
  • the solvent there are exemplified chlorine solvents such as chloroform, methylene chloride, dichloroethane and the like, ether solvents such as tetrahydrofuran and the like, aromatic hydrocarbon solvents such as toluene, xylene and the like, ketone solvents such as acetone, methyl ethyl ketone and the like, and ester solvents such as ethyl acetate, butyl acetate, ethylcellosolve acetate and the like.
  • the polymer binder mixed is preferably that does not disturb charge transport extremely, and that does not have strong absorption of a visible light is suitably used.
  • polymer binder polycarbonate, polyacrylate, poly(methyl acrylate), poly(methyl methacrylate), polystyrene, poly(vinyl chloride), polysiloxane and the like are exemplified.
  • the thickness of the hole transporting layer differs depending on material used, and may properly be selected so that the driving voltage and the light emitting efficiency become optimum values, and at least a thickness at which no pin hole is produced is necessary, and too large thickness is not preferable since the driving voltage of the device increases. Therefore, the thickness of the hole transporting layer is, for example, from 1 nm to 1 ⁇ m, preferably from 2 nm to 500 nm, further preferably from 5 nm to 200 nm.
  • the polymer LED of the present invention has an electron transporting layer
  • known compounds are used as the electron transporting materials, and there are exemplified oxadiazole derivatives, anthraquinonedimethane or derivatives thereof, benzoquinone or derivatives thereof, naphthoquinone or derivatives thereof, anthraquinone or derivatives thereof, tetracyanoanthraquinodimethane or derivatives thereof, fluorenone derivatives, diphenyldicyanoethylene or derivatives thereof, diphenoquinone derivatives, or metal complexes of 8-hydroxyquinoline or derivatives thereof, polyquinoline and derivatives thereof, polyquinoxaline and derivatives thereof, polyfluorene or derivatives thereof, and the like.
  • oxadiazole derivatives benzoquinone or derivatives thereof, anthraquinone or derivatives thereof, or metal complexes of 8-hydroxyquinoline or derivatives thereof, polyquinoline and derivatives thereof, polyquinoxaline and derivatives thereof, polyfluorene or derivatives thereof are preferable, and 2-(4-biphenyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole, benzoquinone, anthraquinone, tris(8-quinolinol)aluminum and polyquinoline are further preferable.
  • the method for forming the electron transporting layer is not particularly restricted, and in the case of an electron transporting material having lower molecular weight, a vapor deposition method from a powder, or a method of film-forming from a solution or melted state is exemplified, and in the case of a polymer electron transporting material, a method of film-forming from a solution or melted state is exemplified, respectively.
  • a polymer binder can be used together.
  • the solvent used in the film-forming from a solution is not particularly restricted provided it can dissolve electron transporting materials and/or polymer binders.
  • the solvent there are exemplified chlorine solvents such as chloroform, methylene chloride, dichloroethane and the like, ether solvents such as tetrahydrofuran and the like, aromatic hydrocarbon solvents such as toluene, xylene and the like, ketone solvents such as acetone, methyl ethyl ketone and the like, and ester solvents such as ethyl acetate, butyl acetate, ethylcellosolve acetate and the like.
  • the film-forming method from a solution or melted state there can be used coating methods such as a spin coating method, casting method, micro gravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method, flexo printing method, offset printing method, inkjet printing method and the like.
  • coating methods such as a spin coating method, casting method, micro gravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method, flexo printing method, offset printing method, inkjet printing method and the like.
  • the polymer binder to be mixed is preferably that which does not extremely disturb a charge transport property, and that does not have strong absorption of a visible light is suitably used.
  • polymer binder poly(N-vinylcarbazole), polyaniline or derivatives thereof, polythiophene or derivatives thereof, poly(p-phenylene vinylene) or derivatives thereof, poly(2,5-thienylene vinylene) or derivatives thereof, polycarbonate, polyacrylate, poly(methyl acrylate), poly(methyl methacrylate), polystyrene, poly(vinyl chloride), polysiloxane and the like are exemplified.
  • the thickness of the electron transporting layer differs depending on material used, and may properly be selected so that the driving voltage and the light emitting efficiency become optimum values, and at least a thickness at which no pin hole is produced is necessary, and too large thickness is not preferable since the driving voltage of the device increases. Therefore, the thickness of the electron transporting layer is, for example, from 1 nm to 1 ⁇ m, preferably from 2 nm to 500 nm, further preferably from 5 nm to 200 nm.
  • the substrate forming the polymer LED of the present invention may preferably be that does not change in forming an electrode and layers of organic materials, and there are exemplified glass, plastics, polymer film, silicon substrates and the like. In the case of a opaque substrate, it is preferable that the opposite electrode is transparent or semitransparent.
  • an anode or a cathode is transparent or semitransparent, and it is preferable that the anode is transparent or semitransparent.
  • electron conductive metal oxide films, semitransparent metal thin films and the like are used.
  • ITO indium-tin-oxide
  • indium zinc oxide and the like which are metal oxide complexes, and gold, platinum, silver, copper and the like are used, and among them, ITO, indium zinc oxide, tin oxide are preferable.
  • a vacuum vapor deposition method, sputtering method, ion plating method, plating method and the like are used.
  • the anode there may also be used organic transparent conducting films such as polyaniline or derivatives thereof, polythiophene or derivatives thereof and the like.
  • the thickness of the anode can be appropriately selected while considering transmission of a light and electric conductivity, and for example, from 10 nm to 10 ⁇ m, preferably from 20 nm to 1 ⁇ m, further preferably from 50 nm to 500 nm.
  • a layer comprising a phthalocyanine derivative conducting polymers, carbon and the like, or a layer having an average film thickness of 2 nm or less comprising a metal oxide, metal fluoride, organic insulating material and the like.
  • a cathode used in the polymer LED of the present invention that having lower work function is preferable.
  • metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, scandium, vanadium, zinc, yttrium, indium, cerium, samarium, europium, terbium, ytterbium and the like, or alloys comprising two of more of them, or alloys comprising one or more of them with one or more of gold, silver, platinum, copper, manganese, titanium, cobalt, nickel, tungsten and tin, graphite or graphite intercalation compounds and the like.
  • alloys include a magnesium-silver alloy, magnesium-indium alloy, magnesium-aluminum alloy, indium-silver alloy, lithium-aluminum alloy, lithium-magnesium alloy, lithium-indium alloy, calcium-aluminum alloy and the like.
  • the cathode may be formed into a laminated structure of two or more layers.
  • the thickness of the cathode can be appropriately selected while considering transmission of a light and electric conductivity, and for example, from 10 nm to 10 ⁇ m, preferably from 20 nm to 1 ⁇ m, further preferably from 50 nm to 500 nm.
  • a vacuum vapor deposition method As the method for fabricating a cathode, there are used a vacuum vapor deposition method, sputtering method, lamination method in which a metal thin film is adhered under heat and pressure, and the like. Further, there may also be provided, between a cathode and an organic layer, a layer comprising an conducting polymer, or a layer having an average film thickness of 2 nm or less comprising a metal oxide, metal fluoride, organic insulation material and the like, and after fabrication of the cathode, a protective layer may also be provided which protects the polymer LED. For stable use of the polymer LED for a long period of time, it is preferable to provide a protective layer and/or protective cover for protection of the device in order to prevent it from outside damage.
  • the protective layer there can be used a polymer, metal oxide, metal fluoride, metal borate and the like.
  • the protective cover there can be used a glass plate, a plastic plate the surface of which has been subjected to lower-water-permeation treatment, and the like, and there is suitably used a method in which the cover is pasted with an device substrate by a thermosetting resin or light-curing resin for sealing. If space is maintained using a spacer, it is easy to prevent an device from being injured.
  • any one means or more are preferably adopted.
  • the polymer LED of the present invention can be suitably used as a flat light source, segment display apparatus, dot-matrix display apparatus, and back light of a liquid crystal display.
  • an anode and a cathode in the plane form may properly be placed so that they are laminated each other.
  • a method in which a mask with a window in pattern form is placed on the above plane light emitting device a method in which an organic layer in non-light emission part is formed to obtain extremely large thickness providing substantial non-light emission, and a method in which any one of an anode or a cathode, or both of them are formed in the pattern.
  • a display device of segment type which can display digits, letters, simple marks and the like.
  • anodes and cathodes are made in the form of stripes and placed so that they cross at right angles.
  • a dot matrix display can be driven by passive driving, or by active driving combined with TFT and the like.
  • the above light emitting device in plane form is a thin self-light-emitting one, and can be suitably used as a flat light source for back-light of a liquid crystal display, or as a flat light source for illumination. Further, if a flexible plate is used, it can also be used as a curved light source or a display.
  • the number average molecular weight and the weight average molecular weight were determined by gel permeation chromatography (GPC) using chloroform solvent as the polystyrene reduced number average molecular weight and the weight average molecular weight, respectively.
  • Flaky magnesium 4.05 g was put in a 500 ml three-necked flask under nitrogen atmosphere. Tetrahydrofuran solution 200 ml of the above 2,2′-dibromo-5,5 1 -dioctyloxy-1,1 1 -biphenyl 45 g was prepared in another flask, and 20 ml of the solution was added in the flask containing magnesium. Five drops of 1,2-dibromoethane as the initiator was added, and heated. When the exothermic reaction started, the remaining solution was added dropwise for 30 minutes. After the dropwise addition, the reaction was conducted for 1 hour with refluxing. Then, it was cooled to 0° C., and tetrahydrofuran 150 ml solution of iodine 44.2 g was added dropwise. After the dropwise adding, the reaction liquid was stirred overnight.
  • Trimethyl borate 38 g and dried tetrahydrofuran 300 ml were charged into another three-necked flask, and the flask was cooled by a dry ice-acetone bath. Using a dropping funnel, the above Grignard reagent solution was added dropwise for 35 minutes. After the dropwise adding the reaction liquid was heated to a room temperature. After having added the reaction liquid to a dilute sulfuric acid (sulfuric acid 12 ml/water 360 ml) and stirring, it was divided into two portions, and each of them was extracted with 150 ml and 100 ml of ethyl acetate. The organic layers were collected together and divided into three portions, and each of them was washed with 100 ml of water.
  • a dilute sulfuric acid sulfuric acid 12 ml/water 360 ml
  • the reaction liquid was filtered under argon atmosphere, and the filtrate was condensed to give a crude product 4.52 g.
  • the resultant crude product was put into a 500 ml three-necked flask whose inside was replaced with argon gas, and dissolved in 90 ml dehydrated ether, and cooled to ⁇ 78° C. Phenyl lithium 23 ml (24 mmol, 1.06M cyclopentane/ether solution) was added dropwise to this solution. After stirring for 20 minutes, it was raised to a room temperature and stirred for 4 hours. Water was added and partitioned and the aqueous layer was extracted with diethyl ether.
  • the polystyrene reduced number average molecular weight of Polymer 1 was 5.0 ⁇ 10 2
  • the polystyrene reduced weight average molecular weight was 6.2 ⁇ 10 3 .
  • this solution was cooled and then poured into a mixed solution of 25% aqueous-ammonia 10 ml/methanol 120 ml/ion-exchanged water 50 ml, and stirred for about 1 hour. Next, resulting precipitate was collected by filtration. The precipitate was washed with ethanol, and dried at a reduced pressure for 2 hours. Next, this precipitate was dissolved in toluene 30 mL, after the addition of 1N hydrochloric-acid 30 mL, it was stirred for 1 hour. The aqueous layer was removed, and 4% aqueous-ammonia 30 mL was added to an organic layer, and after stirring for 1 hour, the aqueous layer was removed.
  • the polystyrene reduced number average molecular weight of Polymer 2 was 6.2 ⁇ 10 3 , and the polystyrene reduced weight average molecular weight was 5.1 ⁇ 10 4 .
  • this solution was cooled and then poured into a mixed solution of 25% aqueous-ammonia 10 ml/methanol 120 ml/ion-exchanged water 50 ml, and stirred for about 1 hour. Next, resulting precipitate was collected by filtration. The precipitate was washed with ethanol, and dried at a reduced pressure for 2 hours. Next, this precipitate was dissolved in toluene 30 mL, after the addition of 1N hydrochloric-acid 30 mL, it was stirred for 1 hour. The aqueous layer was removed, and 4% aqueous-ammonia 30 mL was added to an organic layer, and after stirring for 1 hour, the aqueous layer was removed.
  • the polystyrene reduced number average molecular weight of Polymer 3 was 1.4 ⁇ 10 3 , and the polystyrene reduced weight average molecular weight was 4.9 ⁇ 10 4 .
  • the polystyrene reduced number average molecular weight of Polymer 4 was 1.5 ⁇ 10 3 , and the polystyrene reduced weight average molecular weight was 5.0 ⁇ 10 3 .
  • the polystyrene reduced number average molecular weight of Polymer 5 was 1.6 ⁇ 10 3 , and the polystyrene reduced weight average molecular weight was 5.4 ⁇ 10 3 .
  • the polymer of the present invention is a new polymer which can be used as a light-emitting material, a charge transporting material, etc.

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US20050042195A1 (en) 2005-02-24
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JP5092943B2 (ja) 2012-12-05
EP1318163A1 (en) 2003-06-11
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EP2067808A1 (en) 2009-06-10
KR20030047749A (ko) 2003-06-18
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TW200300770A (en) 2003-06-16

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