WO2009157430A1 - 金属錯体及び有機化合物を含有する組成物及び該組成物を用いてなる発光素子 - Google Patents
金属錯体及び有機化合物を含有する組成物及び該組成物を用いてなる発光素子 Download PDFInfo
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- WO2009157430A1 WO2009157430A1 PCT/JP2009/061367 JP2009061367W WO2009157430A1 WO 2009157430 A1 WO2009157430 A1 WO 2009157430A1 JP 2009061367 W JP2009061367 W JP 2009061367W WO 2009157430 A1 WO2009157430 A1 WO 2009157430A1
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- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000005582 pentacene group Chemical group 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000004894 pentylamino group Chemical group C(CCCC)N* 0.000 description 1
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 125000004346 phenylpentyl group Chemical group C1(=CC=CC=C1)CCCCC* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000011574 phosphorus Chemical group 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000548 poly(silane) polymer Chemical class 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical group CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 125000006308 propyl amino group Chemical group 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 229910001404 rare earth metal oxide Inorganic materials 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000005156 substituted alkylene group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- 125000005579 tetracene group Chemical group 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical group COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
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- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/314—Condensed aromatic systems, e.g. perylene, anthracene or pyrene
- C08G2261/3142—Condensed aromatic systems, e.g. perylene, anthracene or pyrene fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/316—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain bridged by heteroatoms, e.g. N, P, Si or B
- C08G2261/3162—Arylamines
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- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
- C08G2261/3221—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more nitrogen atoms as the only heteroatom, e.g. pyrrole, pyridine or triazole
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/50—Physical properties
- C08G2261/52—Luminescence
- C08G2261/524—Luminescence phosphorescent
- C08G2261/5242—Luminescence phosphorescent electrophosphorescent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/30—Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/10—Transparent electrodes, e.g. using graphene
- H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
- H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
- H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/115—Polyfluorene; Derivatives thereof
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
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- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Definitions
- the present invention relates to a composition containing a metal complex and an organic compound, and a device including these.
- Patent Document 1 a composition of a copolymer and a metal complex containing a fluorenediyl group and a triphenylaminediyl group as repeating units has been proposed (Patent Document 1). .
- an object of the present invention is to provide an organic material from which an element having a low driving voltage can be obtained when used for producing an electroluminescence element or the like.
- the first aspect of the present invention is a composition containing a metal complex represented by the following formula (1) and an organic compound, the lowest unoccupied molecular orbital level (hereinafter referred to as “the metal complex”) calculated by a computational scientific method. , "LUMO”) and the absolute value of the LUMO energy level of the organic compound is less than 0.40 eV.
- M is a metal atom of ruthenium, rhodium, palladium, osmium, iridium or platinum
- R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are each Independently, hydrogen atom, halogen atom, alkyl group, alkoxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkoxy group, arylalkylthio group, acyl group, acyloxy group, amide group, acid Imido group, imine residue, substituted amino group, substituted silyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group, monovalent heterocyclic group, heteroaryloxy group, heteroarylthio group, arylalkenyl group, arylalkynyl A group, a substituted carb
- Z 1 , Z 2 , Z 3 , Z 4 and Z 5 each independently represent a carbon atom or a nitrogen atom. However, at least two of Z 1 , Z 2 , Z 3 , Z 4 and Z 5 are nitrogen atoms. When any of Z 1 , Z 2 , Z 3 , Z 4 and Z 5 is a carbon atom, the hydrogen atom bonded to the carbon atom may be substituted with a substituent.
- the portion represented by represents a monoanionic bidentate ligand.
- R x and R y are atoms bonded to the metal atom M, and each independently represents a carbon atom, an oxygen atom, or a nitrogen atom.
- the present invention is a compound having a residue of a metal complex represented by the formula (1) and a residue of an organic compound, and the LUMO energy level of the metal complex calculated by a computational scientific technique.
- the absolute value of the LUMO energy level of the organic compound is less than 0.40 eV.
- the present invention provides a film and an element using the composition, and a planar light source and illumination using the element.
- the composition of the present invention When the composition and compound of the present invention (hereinafter referred to as “the composition of the present invention”) are used for producing an organic electroluminescence device or the like, a device having a low driving voltage can be obtained, which is a preferred embodiment. Then, a device having excellent luminous efficiency (that is, a high quantum yield) can be obtained. Therefore, the composition of the present invention is particularly useful for the production of a light emitting device such as an organic electroluminescence device.
- composition of the present invention is represented by the formula (1).
- the group represented by the formula (2) is one in which at least two of Z 1 , Z 2 , Z 3 , Z 4 and Z 5 are nitrogen atoms, preferably 2 or 3 are nitrogen atoms. Is. In particular, a combination in which a plurality of these nitrogen atoms are not adjacent (that is, not in adjacent positions) is preferable. Specifically, two or three of Z 1 , Z 2 , Z 3 , Z 4 and Z 5 are nitrogen atoms, and the nitrogen atoms are not adjacent to each other. In the substituent, when any of Z 1 , Z 2 , Z 3 , Z 4 and Z 5 is a carbon atom, a hydrogen atom bonded to the carbon atom may be substituted with a substituent.
- Examples of the group represented by the formula (2) include groups represented by the following formulas. Among these, a group represented by the formula (2-1) and a formula (2-7) Groups are preferred.
- R ′ is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, an acyl group, or an acyloxy group.
- Amide group acid imide group, imine residue, substituted amino group, substituted silyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group, monovalent heterocyclic group, heteroaryloxy group, heteroarylthio group, aryl
- An alkenyl group, an arylalkynyl group, a substituted carboxyl group, or a cyano group, and a plurality of R ′ may be the same or different.
- a halogen atom represented by R ′ alkyl group, alkoxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkoxy group, arylalkylthio group, acyl group, acyloxy group, Amide group, acid imide group, imine residue, substituted amino group, substituted silyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group, monovalent heterocyclic group, heteroaryloxy group, heteroarylthio group, arylalkenyl
- the group, arylalkynyl group, substituted carboxyl group and cyano group have the same definitions and specific examples as those represented by R described later.
- the metal complex represented by the formula (1) includes a metal atom represented by M, a ligand whose number is defined by the subscript m (hereinafter also referred to as “bidentate chelate ligand”), And a monoanionic bidentate ligand represented by the formula (3) whose number is defined by the subscript n (hereinafter also referred to as “monoanionic bidentate ligand”). ing.
- the term “ligand” means both the bidentate chelate ligand and the monoanionic bidentate ligand.
- n is an integer of 0 to 2, preferably 0 or 1, and more preferably 0.
- m + n is the total number of ligands that can be bonded to the metal atom M.
- the central metal is iridium
- the central metal is palladium or platinum
- the atoms and groups represented by R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are specifically the atoms and groups described and exemplified as R below. The same.
- m is preferably 2 or 3 in the formula (1a) from the viewpoint of the stability of the compound.
- the ligand constituting the metal complex affects the emission color, emission intensity, emission efficiency, etc. of the metal complex.
- the metal complex is preferably composed of a ligand having a structure that minimizes the energy deactivation process in the ligand. Furthermore, since the kind and / or substitution position of the substituent that the ligand has affects the electronic properties of the ligand, it affects the properties of the metal complex. From the above viewpoint, it is considered that the metal complex can improve the light emission efficiency, stability, and the like of the metal complex by taking the structure represented by the formula (1).
- R 2 and R 7 in the formula (1) or the formula (1a) is a group represented by the formula (2), and R 7 is represented by the formula (2). Is preferably a group.
- R 7 is represented by the formula (2-1)
- the R 2 is a hydrogen atom
- R 7 is represented by the formula (2-7)
- the R 2 is More preferably, it is a hydrogen atom
- R 2 and R 7 are each independently a group represented by the formula (2-1) or (2-7).
- At least one of the peak wavelengths of the PL (photoluminescence) emission spectrum of the composition of the present invention is preferably 550 nm to 800 nm, more preferably 570 nm to 750 nm, more preferably 570 nm to 700 nm, and particularly preferably. Is 600 nm to 700 nm.
- the metal atom M serving as the central metal of the metal complex is a metal atom of ruthenium, rhodium, palladium, osmium, iridium or platinum. These metal atoms can cause a spin-orbit interaction in the metal complex and cause an intersystem crossing between the singlet state and the triplet state.
- the metal atom M is preferably osmium, iridium, or platinum, more preferably iridium or platinum, and particularly preferably iridium.
- examples of the bidentate chelate ligand include structures represented by the following formulas.
- R represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, an acyl group, an acyloxy group, Amide group, acid imide group, imine residue, substituted amino group, substituted silyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group, monovalent heterocyclic group, heteroaryloxy group, heteroarylthio group, arylalkenyl A group, an arylalkynyl group, a substituted carboxyl group or a cyano group, * represents a site bonded to the
- halogen atom represented by R examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
- the alkyl group represented by R may be linear, branched or cyclic.
- the alkyl group usually has about 1 to 10 carbon atoms.
- Examples of the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, hexyl group, cyclohexyl group, heptyl group, octyl group, 2- And ethylhexyl group, nonyl group, decyl group, 3,7-dimethyloctyl group, lauryl group, trifluoromethyl group, pentafluoroethyl group, perfluorobutyl group, perfluorohexyl group, perfluorooctyl group, etc.
- the alkoxy group represented by R may be linear, branched or cyclic. This alkoxy group usually has about 1 to 10 carbon atoms.
- Alkoxy groups include methoxy, ethoxy, propyloxy, isopropyloxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, cyclohexyloxy, heptyloxy Octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, 3,7-dimethyloctyloxy group, lauryloxy group, trifluoromethoxy group, pentafluoroethoxy group, perfluorobutoxy group, perfluorohexyl group, Perfluorooctyl group, methoxymethyloxy group, 2-methoxyethyloxy group, and the like. Pentyloxy group, hexyloxy group, octyl
- the alkylthio group represented by R may be linear, branched or cyclic.
- the alkylthio group usually has about 1 to 10 carbon atoms.
- Examples of the alkylthio group include methylthio group, ethylthio group, propylthio group, isopropylthio group, butylthio group, isobutylthio group, s-butylthio group, t-butylthio group, pentylthio group, hexylthio group, cyclohexylthio group, heptylthio group, octylthio group , 2-ethylhexylthio group, nonylthio group, decylthio group, 3,7-dimethyloctylthio group, laurylthio group, trifluoromethylthio group, etc., including pentylthio group, hexylthio group, octy
- the aryl group represented by R usually has about 6 to 60 carbon atoms, preferably 7 to 48 carbon atoms.
- Examples of the aryl group include a phenyl group and a C 1 -C 12 alkoxyphenyl group (“C 1 -C 12 alkoxy” means that the alkoxy moiety has 1 to 12 carbon atoms. The same applies hereinafter).
- C 1 -C 12 alkylphenyl group (“C 1 -C 12 alkyl” means that the alkyl moiety has 1 to 12 carbon atoms, the same shall apply hereinafter), a 1-naphthyl group, 2 -Naphtyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, pentafluorophenyl group and the like can be mentioned, and C 1 -C 12 alkoxyphenyl group and C 1 -C 12 alkylphenyl group are preferable.
- the aryl group is an atomic group obtained by removing one hydrogen atom from an aromatic hydrocarbon.
- aromatic hydrocarbon examples include those having a condensed ring and those having two or more independent benzene rings or condensed rings bonded directly or via a group such as vinylene.
- the aryl group may have a substituent, and examples of the substituent include a C 1 to C 12 alkoxyphenyl group and a C 1 to C 12 alkylphenyl group.
- Examples of the C 1 -C 12 alkoxyphenyl group include a methoxyphenyl group, an ethoxyphenyl group, a propyloxyphenyl group, an isopropyloxyphenyl group, a butoxyphenyl group, an isobutoxyphenyl group, an s-butoxyphenyl group, and a t-butoxyphenyl group.
- Pentyloxyphenyl group hexyloxyphenyl group, cyclohexyloxyphenyl group, heptyloxyphenyl group, octyloxyphenyl group, 2-ethylhexyloxyphenyl group, nonyloxyphenyl group, decyloxyphenyl group, 3,7-dimethyloctyloxy Examples thereof include a phenyl group and a lauryloxyphenyl group.
- Examples of the C 1 -C 12 alkylphenyl group include methylphenyl group, ethylphenyl group, dimethylphenyl group, propylphenyl group, mesityl group, methylethylphenyl group, isopropylphenyl group, butylphenyl group, isobutylphenyl group, s- Examples thereof include butylphenyl, t-butylphenyl group, pentylphenyl group, isoamylphenyl group, hexylphenyl group, heptylphenyl group, octylphenyl group, nonylphenyl group, decylphenyl group and dodecylphenyl group.
- the aryloxy group represented by R usually has about 6 to 60 carbon atoms, preferably 7 to 48 carbon atoms.
- Examples of the aryloxy group include a phenoxy group, a C 1 -C 12 alkoxyphenoxy group, a C 1 -C 12 alkylphenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a pentafluorophenyloxy group, and the like.
- a 1 to C 12 alkoxyphenoxy group and a C 1 to C 12 alkylphenoxy group are preferred.
- Examples of the C 1 -C 12 alkoxyphenoxy group include a methoxyphenoxy group, an ethoxyphenoxy group, a propyloxyphenoxy group, an isopropyloxyphenoxy group, a butoxyphenoxy group, an isobutoxyphenoxy group, an s-butoxyphenoxy group, and a t-butoxyphenoxy group.
- Pentyloxyphenoxy group hexyloxyphenoxy group, cyclohexyloxyphenoxy group, heptyloxyphenoxy group, octyloxyphenoxy group, 2-ethylhexyloxyphenoxy group, nonyloxyphenoxy group, decyloxyphenoxy group, 3,7-dimethyloctyloxy Examples thereof include a phenoxy group and a lauryloxyphenoxy group.
- Examples of the C 1 -C 12 alkylphenoxy group include a methylphenoxy group, an ethylphenoxy group, a dimethylphenoxy group, a propylphenoxy group, a 1,3,5-trimethylphenoxy group, a methylethylphenoxy group, an isopropylphenoxy group, and a butylphenoxy group.
- the arylthio group represented by R usually has about 6 to 60 carbon atoms, preferably 7 to 48 carbon atoms.
- the arylalkyl group represented by R usually has about 7 to 60 carbon atoms, preferably 7 to 48 carbon atoms.
- Arylalkyl groups include phenyl-C 1 -C 12 alkyl groups, C 1 -C 12 alkoxyphenyl-C 1 -C 12 alkyl groups, C 1 -C 12 alkylphenyl -C 1 -C 12 alkyl groups, 1- Naphthyl-C 1 -C 12 alkyl group, 2-naphthyl-C 1 -C 12 alkyl group, and the like, C 1 -C 12 alkoxyphenyl-C 1 -C 12 alkyl group, C 1 -C 12 alkylphenyl- C 1 -C 12 alkyl groups are preferred.
- the arylalkoxy group represented by R usually has about 7 to 60 carbon atoms, preferably 7 to 48 carbon atoms.
- phenyl-C 1 -C 12 alkoxy groups such as phenylmethoxy group, phenylethoxy group, phenylbutoxy group, phenylpentyloxy group, phenylhexyloxy group, phenylheptyloxy group, phenyloctyloxy group, C 1 -C 12 alkoxyphenyl-C 1 -C 12 alkoxy group, C 1 -C 12 alkylphenyl-C 1 -C 12 alkoxy group, 1-naphthyl-C 1 -C 12 alkoxy group, 2-naphthyl-C 1 To C 12 alkoxy group and the like, and C 1 to C 12 alkoxyphenyl-C 1 to C 12 alkoxy group and C 1 to C 12 alkylphenyl-C 1 to
- the arylalkylthio group represented by R usually has about 7 to 60 carbon atoms, preferably 7 to 48 carbon atoms.
- the arylalkylthio group includes a phenyl-C 1 -C 12 alkylthio group, a C 1 -C 12 alkoxyphenyl-C 1 -C 12 alkylthio group, a C 1 -C 12 alkylphenyl-C 1 -C 12 alkylthio group, a 1- And naphthyl-C 1 -C 12 alkylthio group, 2-naphthyl-C 1 -C 12 alkylthio group, and the like.
- C 1 -C 12 alkoxyphenyl-C 1 -C 12 alkylthio group, C 1 -C 12 alkylphenyl group C 1 -C 12 alkylthio groups are preferred.
- the acyl group represented by R usually has about 2 to 20 carbon atoms, preferably 2 to 18 carbon atoms.
- Examples of the acyl group include an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, a pivaloyl group, a benzoyl group, a trifluoroacetyl group, and a pentafluorobenzoyl group.
- the acyloxy group represented by R usually has about 2 to 20 carbon atoms, preferably 2 to 18 carbon atoms.
- Examples of the acyloxy group include an acetoxy group, a propionyloxy group, a butyryloxy group, an isobutyryloxy group, a pivaloyloxy group, a benzoyloxy group, a trifluoroacetyloxy group, and a pentafluorobenzoyloxy group.
- the amide group represented by R usually has about 2 to 20 carbon atoms, preferably 2 to 18 carbon atoms.
- As the amide group formamide group, acetamide group, propioamide group, butyroamide group, benzamide group, trifluoroacetamide group, pentafluorobenzamide group, diformamide group, diacetamide group, dipropioamide group, dibutyroamide group, dibenzamide group, ditrifluoro Examples include an acetamide group and a dipentafluorobenzamide group.
- the acid imide group represented by R means a monovalent residue obtained by removing one hydrogen atom bonded to the nitrogen atom from acid imide.
- the acid imide group usually has about 2 to 60 carbon atoms, preferably 2 to 48 carbon atoms.
- Examples of the acid imide group include groups represented by the following structural formulas. (In the formula, a line extending from a nitrogen atom represents a bond, Me represents a methyl group, Et represents an ethyl group, and n-Pr represents an n-propyl group. The same applies hereinafter.)
- the imine residue represented by R is an imine compound (that is, an organic compound having —N ⁇ C— in the molecule. Examples thereof include aldimine, ketimine, and nitrogen atoms in these molecules.
- a compound in which a bonded hydrogen atom is substituted with an alkyl group, etc.) means a monovalent residue obtained by removing one hydrogen atom from This imine residue usually has about 2 to 20 carbon atoms, preferably 2 to 18 carbon atoms. Specific examples include groups represented by the following structural formulas. (Wherein i-Pr represents an isopropyl group, n-Bu represents an n-butyl group, and t-Bu represents a t-butyl group.
- the bond indicated by a wavy line is a “wedge-shaped bond” and / or “ It means “joint represented by a broken line.”
- “joint represented by a wedge shape” means a joint that emerges from the page toward this side, and “joint represented by a broken line”. "Means a bond that is out of the page.)
- the substituted amino group represented by R means an amino group substituted with one or two groups selected from the group consisting of an alkyl group, an aryl group, an arylalkyl group and a monovalent heterocyclic group.
- the alkyl group, aryl group, arylalkyl group or monovalent heterocyclic group may have a substituent.
- the number of carbon atoms of the substituted amino group is usually about 1 to 60, preferably 2 to 48, not including the carbon number of the substituent.
- substituted amino groups include methylamino group, dimethylamino group, ethylamino group, diethylamino group, propylamino group, dipropylamino group, isopropylamino group, diisopropylamino group, butylamino group, isobutylamino group, and s-butylamino group.
- the substituted silyl group represented by R means a silyl group substituted with 1, 2 or 3 groups selected from the group consisting of an alkyl group, an aryl group, an arylalkyl group and a monovalent heterocyclic group. .
- the number of carbon atoms of the substituted silyl group is usually about 1 to 60, preferably 3 to 48.
- the alkyl group, aryl group, arylalkyl group or monovalent heterocyclic group may have a substituent.
- substituted silyl group examples include trimethylsilyl group, triethylsilyl group, tripropylsilyl group, triisopropylsilyl group, dimethylisopropylsilyl group, diethylisopropylsilyl group, t-butyldimethylsilyl group, pentyldimethylsilyl group, hexyldimethylsilyl group, Heptyldimethylsilyl group, octyldimethylsilyl group, 2-ethylhexyl-dimethylsilyl group, nonyldimethylsilyl group, decyldimethylsilyl group, 3,7-dimethyloctyl-dimethylsilyl group, lauryldimethylsilyl group, phenyl-C 1 -C 12 alkylsilyl group, C 1 ⁇ C 12 alkoxyphenyl -C 1 ⁇ C 12 alkylsilyl group
- the substituted silyloxy group represented by R is a silyloxy group substituted with 1, 2 or 3 groups selected from the group consisting of an alkoxy group, an aryloxy group, an arylalkoxy group and a monovalent heterocyclic oxy group. means.
- the substituted silyloxy group usually has about 1 to 60 carbon atoms, preferably 3 to 48 carbon atoms.
- the alkoxy group, aryloxy group, arylalkoxy group or monovalent heterocyclic oxy group may have a substituent.
- Substituted silyloxy groups include trimethylsilyloxy, triethylsilyloxy, tripropylsilyloxy, triisopropylsilyloxy, dimethylisopropylsilyloxy, diethylisopropylsilyloxy, t-butyldimethylsilyloxy, pentyldimethylsilyl Oxy group, hexyldimethylsilyloxy group, heptyldimethylsilyloxy group, octyldimethylsilyloxy group, 2-ethylhexyl-dimethylsilyloxy group, nonyldimethylsilyloxy group, decyldimethylsilyloxy group, 3,7-dimethyloctyl-dimethyl silyloxy group, lauryl dimethyl silyloxy group, a phenyl -C 1 ⁇ C 12 alkyl silyl group, C 1 ⁇ C 12 alkoxypheny
- the substituted silylthio group represented by R means a silylthio group substituted with 1, 2 or 3 groups selected from the group consisting of an alkylthio group, an arylthio group, an arylalkylthio group and a monovalent heterocyclic thio group. To do.
- the carbon number of the substituted silylthio group is usually about 1 to 60, preferably 3 to 48.
- the alkoxy group, arylthio group, arylalkylthio group or monovalent heterocyclic thio group may have a substituent.
- substituted silylthio group examples include trimethylsilylthio group, triethylsilylthio group, tripropylsilylthio group, triisopropylsilylthio group, dimethylisopropylsilylthio group, diethylisopropylsilylthio group, t-butyldimethylsilylthio group, pentyldimethylsilyl group.
- the substituted silylamino group represented by R is a silylamino substituted with 1, 2 or 3 groups selected from the group consisting of an alkylamino group, an arylamino group, an arylalkylamino group and a monovalent heterocyclic amino group Means group.
- the substituted silylamino group usually has about 1 to 60 carbon atoms, preferably 3 to 48 carbon atoms.
- the alkoxy group, arylamino group, arylalkylamino group or monovalent heterocyclic amino group may have a substituent.
- substituted silylamino groups include trimethylsilylamino group, triethylsilylamino group, tripropylsilylamino group, triisopropylsilylamino group, dimethylisopropylsilylamino group, diethylisopropylsilylamino group, t-butyldimethylsilylamino group, pentyldimethylsilyl Amino group, hexyldimethylsilylamino group, heptyldimethylsilylamino group, octyldimethylsilylamino group, 2-ethylhexyl-dimethylsilylamino group, nonyldimethylsilylamino group, decyldimethylsilylamino group, 3,7-dimethyloctyl-dimethyl silylamino group, lauryl dimethylsilyl group, a phenyl -C 1 ⁇ C
- the monovalent heterocyclic group represented by R means the remaining atomic group obtained by removing one hydrogen atom from a heterocyclic compound.
- the carbon number of the monovalent heterocyclic group is usually about 3 to 60, preferably 3 to 20.
- the carbon number of the monovalent heterocyclic group does not include the carbon number of the substituent.
- the heterocyclic compound is an organic compound having a cyclic structure, and the elements constituting the ring include not only carbon atoms but also heteroatoms such as oxygen, sulfur, nitrogen, phosphorus and boron in the ring. Say things.
- Examples of monovalent heterocyclic groups include thienyl group, C 1 -C 12 alkylthienyl group, pyrrolyl group, furyl group, pyridyl group, C 1 -C 12 alkylpyridyl group, piperidyl group, quinolyl group, isoquinolyl group, etc. Of these, a thienyl group, a C 1 -C 12 alkyl thienyl group, a pyridyl group, and a C 1 -C 12 alkyl pyridyl group are preferred.
- the monovalent heterocyclic group is preferably a monovalent aromatic heterocyclic group.
- the heteroaryloxy group represented by R usually has about 6 to 60 carbon atoms, preferably 7 to 48 carbon atoms.
- the heteroaryloxy group, a thienyl group, C 1 ⁇ C 12 alkoxysulfinyl Shichie alkenyl group, C 1 ⁇ C 12 alkyl thienyl group, a pyridyloxy group, a pyridyloxy group, etc. isoquinolyloxy group and the like, C 1 ⁇ C A 12 alkoxypyridyl group and a C 1 -C 12 alkylpyridyl group are preferred.
- Examples of the C 1 -C 12 alkoxypyridyl group include a methoxypyridyl group, an ethoxypyridyl group, a propyloxypyridyl group, an isopropyloxypyridyl group, a butoxypyridyl group, an isobutoxypyridyl group, an s-butoxypyridyl group, and a t-butoxypyridyl group.
- Pentyloxypyridyl group hexyloxypyridyl group, cyclohexyloxypyridyl group, heptyloxypyridyl group, octyloxypyridyl group, 2-ethylhexyloxypyridyl group, nonyloxypyridyl group, decyloxypyridyl group, 3,7-dimethyloctyloxy Examples include a pyridyl group and a lauryloxypyridyl group.
- Examples of the C 1 -C 12 alkylpyridyloxy group include methylpyridyloxy group, ethylpyridyloxy group, dimethylpyridyloxy group, propylpyridyloxy group, 1,3,5-trimethylpyridyloxy group, methylethylpyridyloxy group, Isopropylpyridyloxy group, butylpyridyloxy group, isobutylpyridyloxy group, s-butylpyridyloxy group, t-butylpyridyloxy group, pentylpyridyloxy group, isoamylpyridyloxy group, hexylpyridyloxy group, heptylpyridyloxy group, octyl Examples include pyridyloxy group, nonylpyridyloxy group, decylpyridyloxy group, dodecyl
- the heteroarylthio group represented by R usually has about 6 to 60 carbon atoms, preferably 7 to 48 carbon atoms.
- Examples of the heteroarylthio group include a pyridylthio group, a C 1 -C 12 alkoxypyridylthio group, a C 1 -C 12 alkylpyridylthio group, an isoquinolylthio group, and the like.
- the arylalkenyl group represented by R usually has about 8 to 60 carbon atoms, preferably 8 to 48 carbon atoms.
- a phenyl-C 2 -C 12 alkenyl group (“C 2 -C 12 alkenyl” means that the alkenyl moiety has 2 to 12 carbon atoms, the same shall apply hereinafter).
- C 1 -C 12 alkoxyphenyl-C 2 -C 12 alkenyl group C 1 -C 12 alkylphenyl -C 2 -C 12 alkenyl group, 1-naphthyl-C 2 -C 12 alkenyl group, 2-naphthyl-C 2 C 1 -C 12 alkenyl group, C 1 -C 12 alkoxyphenyl-C 2 -C 12 alkenyl group, C 2 -C 12 alkylphenyl -C 1 -C 12 alkenyl group are preferred.
- the arylalkynyl group represented by R usually has about 8 to 60 carbon atoms, preferably 8 to 48 carbon atoms.
- a phenyl-C 2 -C 12 alkynyl group (“C 2 -C 12 alkynyl” means that the alkynyl moiety has 2 to 12 carbon atoms, the same shall apply hereinafter), C 1 -C 12 alkoxyphenyl-C 2 -C 12 alkynyl group, C 1 -C 12 alkylphenyl -C 2 -C 12 alkynyl group, 1-naphthyl-C 2 -C 12 alkynyl group, 2-naphthyl-C 2 To C 12 alkynyl group and the like, and C 1 to C 12 alkoxyphenyl-C 2 to C 12 alkynyl group and C 1 to C 12 alkylphenyl-C 2 to C 12 alkynyl group are preferable
- the substituted carboxyl group represented by R usually has about 2 to 60 carbon atoms, preferably 2 to 48 carbon atoms, and is an alkyl group, aryl group, arylalkyl group or monovalent complex. It means a carboxyl group substituted with a ring group.
- Examples of the substituted carboxyl group include methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, isopropoxycarbonyl group, butoxycarbonyl group, isobutoxycarbonyl group, s-butoxycarbonyl group, t-butoxycarbonyl group, pentyloxycarbonyl group, hexyl group.
- the arc portion connecting R x and R y in the formula (3) is a divalent group having 3 to 30 atoms other than hydrogen atoms.
- Preferable examples include the following structures. (In the formula, * represents a site bonded to the metal atom M.)
- Examples of the metal complex include those shown below.
- the metal complex M-1 is 1.62 eV
- the metal complex M-3 is 1.92 eV
- the metal complex M-7 is 2.08 eV
- metal complex M-16 is 2.05 eV
- metal complex M-51 is 2.46 eV.
- a metal complex having a short triplet excited state lifetime that easily solves the forbidden transition is preferable from the viewpoint of stable and highly efficient light emission.
- the said metal complex may be used individually by 1 type, or may use 2 or more types together.
- the metal complex can be synthesized, for example, by reacting a compound serving as a ligand with a metal compound in a solution. If necessary, a base, a silver salt compound and the like may be present in the reaction system. Further, the metal complex can be synthesized by a coupling reaction between a metal complex having a 2-phenylpyridine derivative as a ligand and a heterocyclic aromatic compound.
- the reaction temperature for complexing can usually be reacted between the melting point and the boiling point of the solvent, and is preferably ⁇ 78 ° C. to the boiling point of the solvent.
- the reaction time is usually about 30 minutes to 30 hours.
- the reaction can be performed at a temperature equal to or higher than the boiling point of the solvent, and the reaction time is about several minutes to several hours.
- the compound serving as the ligand can be synthesized by, for example, Suzuki coupling, Grignard coupling, Stille coupling, etc., of a 2-phenylpyridine derivative and a heterocyclic aromatic compound. If necessary, it can be synthesized by dissolving in an organic solvent and reacting at a temperature not lower than the melting point of the organic solvent and not higher than the boiling point using, for example, an alkali, an appropriate catalyst, or the like.
- the heterocyclic aromatic compound is “HOUBEN-WEYL METHODS OF ORGANIC CHEMISTRY 4 TH EDITION”, Volume E9b, 1 page, GEORG THIEME VERLAG STUTTGART; HOUBEN-WEYL METHODS OF ORGANIC CHEMISTRY 4 TH EDITION, Volume E9c, page 667. , GEORG THIEME VERLAG STUTTGART and the like.
- the organic compound may be a low-molecular compound or a high-molecular compound, but when used in a light-emitting device, from the viewpoint of device characteristics such as luminous efficiency and life and film-forming properties, the number average molecular weight in terms of polystyrene Is preferably 2 ⁇ 10 3 or more, more preferably 2 ⁇ 10 3 to 1 ⁇ 10 8 , and particularly preferably 1 ⁇ 10 4 to 1 ⁇ 10 6 .
- a compound having a polystyrene-equivalent number average molecular weight of 2 ⁇ 10 3 or more is referred to as a polymer compound, while a compound having a single composition is a low molecular compound (usually a number average molecular weight of 2 ⁇ Less than 10 3 ).
- the organic compound may be an intermediate structure between a low molecular compound and a high molecular compound such as a dendrimer or an oligomer.
- organic compounds examples include triazole derivatives, oxazole derivatives, imidazole derivatives, oxadiazole derivatives, fluorenone derivatives, anthraquinodimethane derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, and compounds having these residues. And triazine derivatives and pyrimidine derivatives are preferable.
- the organic compound from the viewpoint of further reducing the driving voltage, the following formula (A ′): (In the formula, Ar y1 , Ar y2 and Ar y3 each independently represent an aryl group or a monovalent heterocyclic group. Z 6 , Z 7 and Z 8 each independently represent a carbon atom or a nitrogen atom. Provided that at least two of Z 6 , Z 7 and Z 8 are nitrogen atoms, and when any of Z 6 , Z 7 and Z 8 is a carbon atom, the hydrogen atom bonded to the carbon atom is It is preferably a compound represented by the following formula (A): or a compound having a residue thereof.
- Ar x1 and Ar x2 represent an arylene group or a divalent heterocyclic group.
- Ar y3 and Z 6 to Z 8 have the same meaning as described above.
- the compound having a divalent group represented by formula (A) is more preferred, and the compound having a divalent group represented by formula (A) repeats the divalent group represented by formula (A).
- a polymer compound having units as a unit is particularly preferable, and in these, a compound in which Z 6 , Z 7 and Z 8 are nitrogen atoms is particularly preferable.
- the arylene group represented by Ar x1 and Ar x2 includes a phenylene group (for example, the following formulas 1 to 3), a naphthalenediyl group (for example, the following formulas 4 to 13), an anthracene-diyl group (For example, the following formulas 14 to 19), biphenyl-diyl groups (for example, the following formulas 20 to 25), terphenyl-diyl groups (for example, the following formulas 26 to 28), condensed ring compound groups (for example, the following formulas 29 to 29) 35), a fluorene-diyl group (for example, the following formulas 36 to 38), a stilbene-diyl group (the following formulas 39 to 42), a distilben-diyl group (for example, the following formulas 43 and 44), a benzofluorene-diyl group (for example, And the following formulas A-1 to A-3) and dibenzo
- R 3 represents a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an amino group, a substituted amino group, a silyl group, a substituted silyl group, a halogen atom, an acyl group, An acyloxy group, an imine residue, an amide group, an acid imide group, a monovalent heterocyclic group, a carboxyl group, a substituted carboxyl group, a nitro group, or a cyano group, and a plurality of R and R 3 are the same. May be different.
- the aryl group represented by Ar y3 is the same as described and exemplified in the section for the aryl group represented by R.
- Examples of the divalent heterocyclic group represented by Ar x1 and Ar x2 include a pyridinediyl group (for example, the following formulas 45 to 50), a diazaphenylene group (for example, the following formulas 51 to 54), a quinoline diyl group ( For example, the following formulas 55 to 69), quinoxaline diyl groups (for example, the following formulas 70 to 74), acridine diyl groups (for example, the following formulas 75 to 78), bipyridyldiyl groups (for example, the following formulas 79 to 81), phenanthroline diyl
- a divalent heterocyclic group containing nitrogen as a hetero atom such as a group (eg, the following formulas 82 to 84) or a group having a carbazole structure (eg, the following formulas 85 to 87); oxygen, silicon, nitrogen as a hetero atom 5-membered ring heterocyclic groups containing, for example, the following formulas 88 to 92
- heteroatoms for example, the following formula 9 To 103
- a 5-membered ring heterocyclic group containing oxygen, silicon, nitrogen, sulfur, selenium, etc. as a heteroatom and bonded to the ⁇ -position of the heteroatom to form a dimer or oligomer for example, Formulas 104 to 105: a 5-membered heterocyclic group containing oxygen, silicon, nitrogen, sulfur, selenium or the like as a hetero atom, and a group bonded to the phenyl group at the ⁇ -position of the hetero atom (for example, the following formula 106 To 112); groups in which a phenyl group, a furyl group, or a thienyl group is substituted on a 5-membered condensed heterocyclic group containing oxygen, nitrogen, sulfur or the like as a hetero atom (for example, the following formulas 113 to 118).
- the monovalent heterocyclic group represented by Aly3 is the same as described and exemplified as the monovalent heterocyclic group represented by R.
- the aryl group represented by Ar y1 and Ar y2 is described and exemplified as the arylene group represented by Ar x1 and Ar x2 , and is one of two bonds. Is the same as that in which R is replaced.
- the aryl group represented by Ar y3 is the same as described and exemplified as the aryl group represented by R.
- the monovalent heterocyclic group represented by Ar y3 is the same as described and exemplified as the monovalent heterocyclic group represented by R.
- the substituents that the groups represented by Ar x1 to Ar x3 and Ar y1 to Ar y3 may have include an alkyl group, an alkoxy group, an alkylthio group, and an aryl group.
- substituents are the same as those described and exemplified as the group and atom represented by R.
- Examples of the divalent group represented by the formula (A) include the following.
- the organic compound is a polymer compound
- a conjugated polymer is preferable from the viewpoint of charge transportability when formed into a thin film and device characteristics such as light emission efficiency and lifetime when used in a light emitting device.
- the conjugated polymer means a polymer compound in which delocalized ⁇ electron pairs exist along the main chain skeleton of the polymer. As this delocalized electron, an unpaired electron or a lone electron pair may participate in resonance instead of a double bond.
- the organic compound when the organic compound is a polymer compound, the organic compound may be linked with non-conjugated units within a range not impairing the light emission characteristics and charge transport characteristics, or the repeating unit may contain those non-conjugated parts. Good.
- the non-conjugated bond structure include a structure represented by the following formula and a structure in which two or more of the structures represented by the following formula are combined. In the formulas shown below, R has the same meaning as described above.
- Ar represents an aromatic hydrocarbon ring or a heterocyclic ring.
- the organic compound when it is a polymer compound, it may be a random copolymer, a block copolymer or a graft copolymer, or a polymer having an intermediate structure thereof, for example, a blocky property It may be a random copolymer. From the viewpoint of obtaining a polymer light emitter having a high quantum yield of fluorescence or phosphorescence, a random copolymer having a block property, a block copolymer, or a graft copolymer is preferable to a complete random copolymer. Furthermore, the organic compounds include those having a branch in the main chain and having three or more terminal portions and dendrimers.
- the polymer compound having a divalent group represented by the formula (A) as a repeating unit is further represented by the following formula (B): -(Ar 2 )-(B) (In the formula, Ar 2 represents an arylene group which may have a substituent, or a divalent heterocyclic group which may have a substituent.) It may have a repeating unit represented by
- the arylene group which may have a substituent represented by Ar 2 may be a phenylene group which may have a substituent or a naphthylene group which may have a substituent.
- groups represented by the following formula (3a) In the formula, the P ring and the Q ring each independently represent an aromatic ring, but the P ring may or may not be present.
- the 5-membered ring or 6-membered ring is independently an alkyl group, alkoxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkoxy group, arylalkylthio group, arylalkenyl group, aryl.
- an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy which is a substituent that the 5-membered or 6-membered ring including the P ring, the Q ring, and Y 1 may have Group, arylthio group, arylalkyl group, arylalkoxy group, arylalkylthio group, arylalkenyl group, arylalkynyl group, amino group, substituted amino group, silyl group, substituted silyl group, halogen atom, acyl group, acyloxy group, imine residue
- the group, amide group, acid imide group, monovalent heterocyclic group, carboxyl group, substituted carboxyl group and cyano group are the same as those described and exemplified as the group and atom represented by R.
- the divalent heterocyclic group represented by Ar 2 refers to the remaining atomic group obtained by removing two hydrogen atoms from the heterocyclic compound, and the group has a substituent. May be.
- the heterocyclic compound is an organic compound having a cyclic structure, and the elements constituting the ring are not only carbon atoms, but also oxygen atoms, nitrogen atoms, silicon atoms, germanium atoms, tin atoms, phosphorus atoms, boron atoms And having at least one atom selected from the group consisting of a sulfur atom, a selenium atom and a tellurium atom.
- the divalent heterocyclic group is preferably a divalent aromatic heterocyclic group.
- the number of carbon atoms in the portion excluding the substituent of the divalent heterocyclic group is usually about 3 to 60.
- the total number of carbon atoms including the substituents of the divalent heterocyclic group is usually about 3 to 100.
- examples of the divalent heterocyclic group represented by Ar 2 include the following formula (3b):
- the P ′ ring and the Q ′ ring each independently represent an aromatic ring, but the P ′ ring may or may not be present.
- the P ′ ring may or may not be present.
- the P ′ ring is not present, they are respectively present on the 5-membered ring or 6-membered ring containing Y 2 or the Q ′ ring.
- the ring, the Q ′ ring and the 5-membered or 6-membered ring containing Y 2 are each independently an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, Arylalkylthio group, arylalkenyl group, arylalkynyl group, amino group, substituted amino group, silyl group, substituted silyl group, halogen atom, acyl group, acyloxy group, imine residue, amide group, acid imide group, monovalent complex Ring group, carboxyl , At least one of which may have a substituent .Y 2 selected from the group consisting of substituted carboxyl group and cyano group, -O -, - S -, - Se -, - B (R 6) -, —Si (R 7 ) (R 8
- R 6 to R 10 , R 13 , R 18 to R 31 and R 34 to R 36 are each independently a hydrogen atom, alkyl group, alkoxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group Aria Kokishi group, arylalkylthio group, arylalkenyl group, arylalkynyl group, amino group, substituted amino group, silyl group, substituted silyl group, silyloxy group, substituted silyloxy group, monovalent heterocyclic group or halogen atom.) The group represented by these is mentioned.
- an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio which is a substituent that the 5-membered or 6-membered ring including the P ′ ring, the Q ′ ring, and Y 2 may have.
- Arylalkoxy group, arylalkylthio group, arylalkenyl group, arylalkynyl group, amino group, substituted amino group, silyl group, substituted silyl group, silyloxy group, substituted silyloxy group, monovalent heterocyclic group and halogen atom are The groups and atoms represented by R are the same as those described and exemplified as the atoms.
- Examples of the group represented by the formula (3a) and the formula (3b) include the following formula (3-1), the following formula (3-2), and the following formula (3-3): (In the formula, A ring, B ring and C ring each independently represent an aromatic ring.
- Formulas (3-1), (3-2) and (3-3) are an alkyl group, an alkoxy group, an alkylthio group, respectively.
- D ring, E ring, F ring and G ring are each independently an alkyl group, alkoxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkoxy group, arylalkylthio group.
- An aromatic ring optionally having one or more substituents selected from the group consisting of a carboxyl group, a substituted carboxyl group and a cyano group, Y represents the same meaning as described above.
- a group represented by the formula (3-4) or the formula (3-5) is preferable.
- Y is preferably —S—, —O—, —C (R 11 ) (R 12 ) — from the viewpoint of high luminous efficiency, more preferably —S—, —O—. is there.
- R 11 and R 12 represent the same meaning as described above.
- aromatic rings in the above formulas (3-1) to (3-5) include aromatic hydrocarbon rings such as benzene ring, naphthalene ring, anthracene ring, tetracene ring, pentacene ring, pyrene ring, phenanthrene ring; pyridine ring, Heteroaromatic rings such as bipyridine ring, phenanthroline ring, quinoline ring, isoquinoline ring, thiophene ring, furan ring, and pyrrole ring can be mentioned.
- aromatic hydrocarbon rings such as benzene ring, naphthalene ring, anthracene ring, tetracene ring, pentacene ring, pyrene ring, phenanthrene ring
- pyridine ring Heteroaromatic rings such as bipyridine ring, phenanthroline ring, quinoline ring, isoquinoline ring, thiophene
- Examples of the substituent that the groups represented by the formulas (3-1) to (3-5) may have include an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, and an arylalkyl group.
- a cyclic group, a carboxyl group, and a substituted carboxyl group are preferable.
- R 109 , R 110 , R 111 , R 112 , R 113 and R 114 are each independently a hydrogen atom, a halogen atom, an alkyl group, an alkyloxy group, an alkylthio group, an aryl group, an aryloxy group, Arylthio group, arylalkyl group, arylalkyloxy group, arylalkylthio group, alkenyl group, alkynyl group, arylalkenyl group, arylalkynyl group, acyl group, acyloxy group, amide group, acid imide group, imine residue, substituted amino group Substituted silyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group, cyano group, nitro group, monovalent heterocyclic group, heteroaryloxy group, hetero
- Examples of the repeating unit represented by the formula (B) include the repeating units represented by the following formulas B-1 to B-8.
- the polymer compound having a divalent group represented by the formula (A) as a repeating unit may further have a divalent aromatic amine group as a repeating unit.
- the divalent aromatic amine group the following formula (5): (In the formula, Ar 6 , Ar 7 , Ar 8 and Ar 9 each independently represent an arylene group or a divalent heterocyclic group. Ar 6 , Ar 7 and Ar 8 are bonded to each other to form a ring.
- Ar 10 , Ar 11 and Ar 12 each independently represents an aryl group or a monovalent heterocyclic group, Ar 6 to Ar 12 may have a substituent, and x and y are Each independently 0 or 1 and 0 ⁇ x + y ⁇ 1.)
- the repeating unit represented by is preferable.
- the arylene group and divalent heterocyclic group represented by Ar 6 to Ar 9 are the same as those described and exemplified as the divalent heterocyclic group represented by Ar.
- the aryl group and monovalent heterocyclic group represented by Ar 10 to Ar 12 are the same as those explained and exemplified as the aryl group and monovalent heterocyclic group represented by R. It is.
- the arylene group, divalent heterocyclic group, aryl group and monovalent heterocyclic group optionally have an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryl group.
- Examples of the repeating unit represented by the formula (5) include the repeating units represented by the following formulas C-1 to C-11.
- the hydrogen atom on the aromatic ring is independently an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a phenylalkyl group having 7 to 26 carbon atoms, or 7 to 7 carbon atoms.
- phenylalkoxy group phenyl group, phenoxy group, alkyl group-substituted phenyl group having 7 to 26 carbon atoms, alkoxy group-substituted phenyl group having 7 to 26 carbon atoms, alkylcarbonyl group having 2 to 21 carbon atoms, formyl
- the group may be substituted with a group, an alkoxycarbonyl group having 2 to 21 carbon atoms, or a carboxyl group. When two substituents are present, they may be bonded to each other to form a ring.
- phenylalkyl group examples include those having 7 to 26, preferably 11 to 21, and more preferably 14 to 18 carbon atoms, and specifically include phenylmethyl group, phenylethyl group, phenylpropyl group, phenylbutyl group. Group, phenylpentyl group, phenylhexyl group, phenylheptyl group, phenyloctyl group, phenylnonyl group, phenyldecyl group, phenyldodecyl group and the like.
- phenylalkoxy group examples include those having 7 to 26 carbon atoms, preferably 11 to 21, more preferably 14 to 18, and specifically include phenylmethoxy group, phenylethoxy group, phenylpropyloxy group, Examples thereof include a phenylbutoxy group, a phenylpentyloxy group, a phenylhexyloxy group, a phenylheptyloxy group, a phenyloctyloxy group, a phenylnonyloxy group, a phenyldecyloxy group, and a phenyldodecyloxy group.
- the alkyl group-substituted phenyl group is a group in which one or more hydrogen atoms on the phenyl group are substituted with an alkyl group having 1 to 20 carbon atoms, that is, a monoalkylphenyl group, a dialkylphenyl group, a trialkylphenyl group, It refers to a tetraalkylphenyl group and a pentaalkylphenyl group.
- Examples of the alkyl group-substituted phenyl group include those having 7 to 26 carbon atoms, preferably 11 to 21 carbon atoms, more preferably 14 to 18 carbon atoms, and specifically include mono, di, tri, tetra, or pentamethyl.
- Mono, di, tri, tetra, or pentaethylphenyl group mono, di, tri, tetra, or pentapropylphenyl group; mono, di, tri, tetra, or pentaisopropylphenyl group; mono, di, tri Mono, di, tri, tetra, or pentaisobutylphenyl group; mono, di, tri, tetra, or penta-s-butylphenyl group; mono, di, tri, tetra, or penta -T-butylphenyl group; mono, di, tri, tetra or pentapentylphenyl group; mono, di, tri, tetra or pentaisoa Mono, di, tri, tetra, or pentahexylphenyl group; mono, di, tri, tetra, or pentaheptylphenyl group; mono, di, tri, tetra, or pent
- the alkoxy group-substituted phenyl group is a group in which one or more hydrogen atoms on the phenyl group are substituted with an alkoxy group having 1 to 20 carbon atoms, that is, a monoalkoxyphenyl group, a dialkoxyphenyl group, a trialkoxyphenyl group. , Tetraalkoxyphenyl group, and pentaalkoxyphenyl group.
- Examples of the alkoxy group-substituted phenyl group include those having 7 to 26 carbon atoms, preferably 11 to 21 carbon atoms, more preferably 14 to 18 carbon atoms, and specifically include mono, di, tri, tetra, or pentamethoxy.
- Mono, di, tri, tetra, or pentaethoxyphenyl group mono, di, tri, tetra, or pentapropyloxyphenyl group; mono, di, tri, tetra, or pentaisopropyloxyphenyl group; mono, di Mono, di, tri, tetra, or pentaisobutoxyphenyl group; mono, di, tri, tetra, or penta-s-butoxyphenyl group; mono, di, tri, tetra Or penta-t-butoxyphenyl group; mono, di, tri, tetra, or pentapentyloxyphenyl group; mono, di Tri, tetra, or pentahexyloxyphenyl group; mono, di, tri, tetra, or pentaheptyloxyphenyl group; mono, di, tri, tetra, or pentaoctyloxyphenyl group; mono, di, tri, t
- alkylcarbonyl group examples include those having 2 to 21 carbon atoms, preferably 5 to 15 carbon atoms, more preferably 8 to 12 carbon atoms, and specific examples include acetyl group, propionyl group, butyryl group, isobutyryl group, and pentanoyl group.
- alkoxycarbonyl group examples include those having 2 to 21, preferably 5 to 15, and more preferably 8 to 12 carbon atoms. Specific examples include a methoxycarbonyl group, an ethoxycarbonyl group, a propyloxycarbonyl group, Isopropyloxycarbonyl group, butoxycarbonyl group, isobutoxycarbonyl group, s-butoxycarbonyl group, t-butoxycarbonyl group, pentyloxycarbonyl group, hexyloxycarbonyl group, heptyloxycarbonyl group, octyloxycarbonyl group, 2-ethylhexyloxy Examples include carbonyl group, nonyloxycarbonyl group, decyloxycarbonyl group, 3,7-dimethyloctyloxycarbonyl group, dodecyloxycarbonyl group and the like.
- R 3 , R 4 and R 5 are independently an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a phenylalkyl group having 7 to 26 carbon atoms, a carbon atom 7-26 phenylalkoxy group, phenyl group, phenoxy group, alkyl group-substituted phenyl group having 7-26 carbon atoms, alkoxy group-substituted phenyl group having 7-26 carbon atoms, alkylcarbonyl having 2-21 carbon atoms Represents a group, a formyl group, an alkoxycarbonyl group having 2 to 21 carbon atoms, or a carboxyl group, or R 3 and R 4 are combined to form a ring instead of the above groups.
- X and y are each independently an integer of 0 to 4, z is 1 or 2, and w is an integer of 0 to 5.
- R 3 , R 4 and R 5 There are a plurality of at least one of R 3 , R 4 and R 5. If you want that multiple It may not be the same or different.)
- the repeating unit represented by is preferable.
- the ring may have a substituent.
- substituents include 5 to C 14 heterocycles.
- heterocyclic ring include a morpholine ring, a thiomorpholine ring, a pyrrole ring, a piperidine ring, and a piperazine ring.
- Examples of such a repeating unit represented by the formula (6) include repeating units represented by the following formulas (6-1) to (6-10).
- Examples of the organic compound (low molecular weight compound) represented by the formula (A ′) include the following.
- the organic compound preferably has a LUMO energy level value of -1.00 to -2.50 eV, more preferably -1.30 to -2.40 eV, from the viewpoint of reducing driving voltage. .
- the organic compounds may be used alone or in combination of two or more.
- the difference between the absolute value of the LUMO energy level of the metal complex and the absolute value of the LUMO energy level of the organic compound is less than 0.40 eV, preferably 0.35 eV or less, More preferably, it is 0.30 eV or less, but it is desirable that the LUMO energy of the metal complex is smaller than the LUMO energy of the organic compound from the viewpoint of luminous efficiency.
- a combination of a metal complex and an organic compound in which the difference between the absolute value of the LUMO energy level of the metal complex and the absolute value of the LUMO energy level of the organic compound is less than 0.40 eV is, for example, The following modes are conceivable. 1) Combination of one metal complex and one organic compound Combination in which the difference between the absolute value of the LUMO energy level of the metal complex and the absolute value of the LUMO energy level of the organic compound is less than 0.40 eV.
- the value of the LUMO energy level is a value calculated by a computational scientific method.
- the computational scientific method is a quantum chemical calculation program Gaussian 03, and a B3LYP level density functional method is used to optimize the structure of the ground state, and the LUMO energy level of the optimized structure is Calculate the value.
- LANL2DZ is used for the central metal atom as a basis function
- 6-31 g * is used for the other atoms.
- the LUMO energy level means that when the organic compound is a polymer compound and has a repeating unit, a trimer is formed by all possible combinations of the repeating unit of the organic compound,
- the absolute value of the LUMO energy level is determined, the absolute value of the LUMO energy level at which the absolute value is maximum is determined by the absolute value of the LUMO energy level of the organic compound (that is, the value of the LUMO energy level is In the case of a negative value, the absolute value means a value having the negative sign, which is the same in this specification).
- the above-mentioned computational scientific method is applied to the organic compound itself, and the absolute value of the required LUMO energy level is calculated as follows. It is defined as the absolute value of the LUMO energy level of the organic compound.
- the organic compound is: For example, (A′-1) to (A′-31); when the metal complex is M-10, M-11, M-12, the organic compound is, for example, (A′-1) to (A A′-31); when the metal complex is M-20, the organic compounds are, for example, (A′-5) to (A′-12), (A′-26) to (A′-28).
- the organic compound includes, for example, (A′-5) to (A′-12), (A ′ A low molecular compound of -26) to (A'-28), a divalent group represented by any of (A-5) to (A-12), and (A-26) to (A-28); It is a polymer compound composed of repeating unit F8.
- composition of the present invention may contain a charge transport material and / or a light emitting material.
- the charge transport material is classified into a hole transport material and an electron transport material, and includes an organic compound (low molecular organic compound and / or high molecular organic compound) and the like.
- Examples of the hole transport material include aromatic amines, carbazole derivatives, polyparaphenylene derivatives, and the like, which are known as hole transport materials for organic electroluminescence elements.
- Examples of the electron transport material include those known as electron transport materials for organic electroluminescence devices, such as oxadiazole derivatives anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetra And metal complexes of cyanoanthraquinodimethane and derivatives thereof, fluorenone derivatives, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives and 8-hydroxyquinoline and derivatives thereof.
- the low-molecular organic compound of the charge transport material means a host compound or a charge injection / transport compound used for a low-molecular organic electroluminescence device.
- organic EL display Sudoki Tokito, Adachi Chiba and Hideyuki Murata, Ohm Co., Ltd., page 107, monthly publication (vol. 9, No. 9, pages 26-30, 2003), JP-A-2004-244400, JP-A-2004-277377, etc.
- the minimum triplet excitation energy of these charge transport materials is less than the minimum triplet excitation energy of the metal complex. Is also preferably large.
- Examples of the polymer organic compound of the charge transport material include non-conjugated polymers and conjugated polymers.
- Examples of the non-conjugated polymer include polyvinyl carbazole.
- Examples of the conjugated polymer include a polymer having an aromatic ring in the main chain.
- the conjugated polymer has a phenylene group which may have a substituent, a fluorene which may have a substituent, or a substituent.
- Dibenzothiophene which may have a substituent, dibenzofuran which may have a substituent, dibenzosilole which may have a substituent, etc. in the main chain as a repeating unit, and copolymers with those units It is done.
- a polymer compound having a benzene ring which may have a substituent as a partial structure is exemplified. More specifically, for example, JP2003-231741, JP2004059899, JP2004002654, JP2004-292546, US5708130, WO99 / 54385, WO00 / 46321, WO02 / 077060, “Organic EL Display” (Shitoki Tokito, Chiba Yasada, Hideyuki Murata, Ohmsha), p. 111, Monthly Display (vol. 9, No. 9, 2002), pages 47-51, etc. Examples include polymers.
- polymer organic compound of the charge transport material examples include a polymer containing a repeating unit represented by the formula (3a) or (3b).
- the following groups that is, the following examples
- the parentheses are excluded
- those containing the following structures as repeating units those containing the following structures as repeating units.
- the lowest triplet excitation energy (TH) of the low-molecular organic compound or high-molecular organic compound of the charge transport material and the lowest triplet excitation energy (TM) of the metal complex are: TH> TM-0.2 (eV) It is preferable to satisfy the relationship.
- the polymer organic compound of the charge transport material has a polystyrene-equivalent number average molecular weight of preferably 1 ⁇ 10 3 to 1 ⁇ 10 8 , more preferably 1 ⁇ 10 4 to 1 ⁇ 10 8. 6 .
- the weight average molecular weight of the polymer in terms of polystyrene is preferably 1 ⁇ 10 3 to 1 ⁇ 10 8 , and more preferably 5 ⁇ 10 4 to 5 ⁇ 10 6 .
- the light-emitting material known materials can be used. For example, naphthalene derivatives, anthracene and derivatives thereof, perylene and derivatives thereof, polymethine series, xanthene series, coumarin series, cyanine series pigments, 8-hydroxyquinoline and the like.
- Low molecular light emitting materials such as metal complexes of derivatives, aromatic amines, tetraphenylcyclopentadiene and derivatives thereof, tetraphenylbutadiene and derivatives thereof, and the like.
- the compounding amount of the metal complex varies depending on the type of organic compound to be combined and the characteristics to be optimized, but usually 0.05 to 100 parts by weight when the amount of the organic compound is 100 parts by weight. Preferably, the amount is 0.1 to 30 parts by weight.
- the composition of the present invention may contain a solvent or a dispersion medium.
- the solvent and the dispersion medium those which are stable by dissolving or dispersing the thin film components can be appropriately selected from known solvents.
- the solvent include chlorinated solvents (chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o-dichlorobenzene, etc.), ether solvents (tetrahydrofuran, dioxane, etc.), aromatic carbonization.
- Hydrogen solvents (benzene, toluene, xylene, etc.), aliphatic hydrocarbon solvents (cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane, etc.) , Ketone solvents (acetone, methyl ethyl ketone, cyclohexanone, etc.), ester solvents (ethyl acetate, butyl acetate, ethyl cellosolve acetate, etc.), polyhydric alcohols and their derivatives (ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether) , Ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycer
- the composition may contain additional additives in order to improve the dischargeability and reproducibility of the composition.
- Additional additives include high boiling point solvents (anisole, bicyclohexylbenzene, etc.) and the like in order to suppress evaporation from the nozzle.
- the composition containing the solvent or dispersion medium preferably has a viscosity at 25 ° C. of 1 to 100 mPa ⁇ s.
- the compound of the present invention is a compound having a residue of a metal complex represented by the above formula (1) and a residue of an organic compound, and has an LUMO energy level of the metal complex calculated by a computational scientific method.
- a compound in which the difference between the absolute value and the absolute value of the LUMO energy level of the organic compound is less than 0.40 eV.
- the compound of the present invention is typically a polymer compound, and as the polymer compound, 1.
- the main chain has a residue of a metal complex, in addition to those in which the metal complex is incorporated in the main chain of the linear polymer, those in which three or more polymer chains are bonded from the metal complex are also included.
- the organic compound includes a residue of a metal complex having a structure represented by the formula (1) or the like, and has a polystyrene-equivalent number average molecular weight of 1 ⁇ 10 3 to 1 ⁇ 10 8 , Those having a residue of a metal complex having a structure represented by the above formula (1) or the like in the main chain or terminal or at least two of them.
- the polymer compound having a metal complex residue in the main chain of the polymer organic compound is represented by any of the following formulas, for example. (Wherein, M 1, M 2 represents a residue of a metal complex, the bond is. The M 1, M 2 with the ligand of the metal complex by the binding hand, the polymeric backbone (The solid line represents the molecular chain.)
- the polymer compound having a metal complex residue at the terminal of the polymer organic compound is represented by the following formula, for example.
- M 3 represents a monovalent residue of a metal complex, and the bond of the metal complex has a ligand.
- the M 3 is bonded to X by the bond.
- X Represents a single bond, an optionally substituted alkenylene group, an optionally substituted alkynylene group, an optionally substituted arylene group, or an optionally substituted divalent heterocyclic group. Represents a chain.
- the polymer compound having a metal complex residue in the side chain of the polymer organic compound is represented, for example, by the formula: —Ar′—.
- Ar ′ represents a divalent aromatic group or an atom selected from the group consisting of oxygen atom, silicon atom, germanium atom, tin atom, phosphorus atom, boron atom, sulfur atom, selenium atom and tellurium atom.
- Ar ′ has 1 to 4 groups represented by —L—X, X represents a monovalent residue of a metal complex, and L represents Single bond, —O—, —S—, —C ( ⁇ O) —, —C ( ⁇ O) O—, —S ( ⁇ O) —, —S ( ⁇ O 2 ) —, —Si (R 68 ) (R 69 ) —, N (R 70 ) —, —B (R 71 ) —, —P (R 72 ) —, —P ( ⁇ O) (R 73 ) —, an optionally substituted alkylene group Represents an optionally substituted alkenylene group, an optionally substituted alkynylene group, an optionally substituted arylene group, or an optionally substituted divalent heterocyclic group.
- the alkylene group, the alkenylene group, the alkynylene group is -CH 2 - when containing group, -CH 2 contained in the alkylene group - group 1 or more, -CH 2 contained in the alkenylene group - the group
- One or more of the —CH 2 — groups contained in the alkynylene group are —O—, —S—, —C ( ⁇ O) —, —C ( ⁇ O) O—, —S, respectively.
- R 68 , R 69 , R 70 , R 71 , R 72 , R 73 , R 74 , R 75 , R 76 , R 77 , R 78 , and R 79 are each independently a hydrogen atom, an alkyl group, or an aryl group A group selected from the group consisting of a monovalent heterocyclic group and a cyano group is represented.
- Ar ′ represents an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, an arylalkenyl group in addition to the group represented by —L—X.
- an alkyl group represented by R 68 , R 69 , R 70 , R 71 , R 72 , R 73 , R 74 , R 75 , R 76 , R 77 , R 78 , and R 79 , an aryl group, A monovalent heterocyclic group, a cyano group, and an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, which are substituents that Ar ′ may have , Arylalkylthio group, arylalkenyl group, arylalkynyl group, amino group, substituted amino group, silyl group, substituted silyl group, halogen atom, acyl group, acyloxy group, imine residue, amide group, acid imide group, monovalent The heterocyclic group, carboxyl group,
- examples of the divalent aromatic group include a phenylene group, a pyridinylene group, a pyrimidylene group, and a naphthylene group.
- the divalent heterocyclic group is the same as described and exemplified as the divalent heterocyclic group represented by Ar x1 and Ar x2 .
- the compound of the present invention is preferably a conjugated polymer having excellent carrier (electron or hole) transportability.
- the absolute value of the LUMO energy level of the metal complex and the absolute value of the LUMO energy level of the organic compound are defined as follows (1) to (3).
- the compound of the present invention is a polymer compound (copolymer) having a repeating unit having a metal complex residue: Absolute value of LUMO energy level of the metal complex: repeating unit having a metal complex residue The absolute value of the LUMO energy level in the monomer. Absolute value of LUMO energy level of organic compound: When a trimer is formed for all possible combinations of other repeating units of a polymer compound, and the absolute value of LUMO energy level of the trimer is determined In addition, the absolute value of the LUMO energy level that has the maximum absolute value.
- the absolute value of the LUMO energy level of the metal complex a metal obtained by replacing the bond in the metal complex residue with a hydrogen atom Absolute value of LUMO energy level of the complex.
- Absolute value of LUMO energy level of organic compound When a trimer was formed for all possible combinations of repeating units of a polymer compound, and the absolute value of LUMO energy level of the trimer was determined, The absolute value of the LUMO energy level that maximizes the absolute value.
- Absolute value of the LUMO energy level of the metal complex LUMO of the metal complex in which the bond in the residue of the metal complex is replaced with a hydrogen atom Absolute value of energy level.
- Absolute value of LUMO energy level of organic compound The absolute value of LUMO energy level of an organic compound in which a bond is replaced with a hydrogen atom in a portion other than the residue of the metal complex in the compound.
- the element of the present invention is formed by using the composition of the present invention.
- the element includes an electrode composed of an anode and a cathode, and a layer provided between the electrodes and containing the metal complex and the organic compound. is there.
- a film can be formed using the composition of the present invention, and the device of the present invention can be manufactured using this film.
- the element of the present invention is a light emitting element will be described as a typical example.
- the light-emitting element of the present invention includes a pair of electrodes composed of an anode and a cathode, and a thin film composed of a single layer (single layer type) or a plurality of layers (multilayer type) having at least a light emitting layer between the electrodes. . At least one of the thin film layers is formed using the composition of the present invention.
- the total content of the metal complex and the organic compound in the thin film is usually 0.1 to 100% by weight, preferably 0.1 to 30% by weight, based on the weight of the entire light emitting layer. 0.5 to 15% by weight is more preferable, and 1 to 10% by weight is particularly preferable.
- the thin film is a light emitting layer, and the light emitting layer contains the metal complex.
- the light emitting element of this invention is a multilayer type, it takes the following layer structure, for example.
- the anode of the light emitting device of the present invention supplies holes to a hole injection layer, a hole transport layer, a light emitting layer and the like, and it is effective to have a work function of 4.5 eV or more.
- a material for the anode metals, alloys, metal oxides, electrically conductive compounds, mixtures thereof, and the like can be used.
- conductive metal oxides such as tin oxide, zinc oxide, indium oxide and indium tin oxide (ITO), metals such as gold, silver, chromium and nickel, and these conductive metal oxides and metals
- ITO indium oxide
- Inorganic conductive materials such as copper iodide and copper sulfide, polyanilines, polythiophenes (such as PEDOT), organic conductive materials such as polypyrrole, and laminates of these with ITO.
- the cathode of the light emitting device of the present invention supplies electrons to an electron injection layer, an electron transport layer, a light emitting layer, and the like.
- a material for the cathode a metal, an alloy, a metal halide, a metal oxide, an electrically conductive compound, or a mixture thereof can be used.
- Cathode materials include alkali metals (lithium, sodium, potassium, etc.) and their fluorides and oxides, alkaline earth metals (magnesium, calcium, barium, cesium, etc.) and their fluorides and oxides, gold, silver, Lead, aluminum, alloys and mixed metals (sodium-potassium alloy, sodium-potassium mixed metal, lithium-aluminum alloy, lithium-aluminum mixed metal, magnesium-silver alloy, magnesium-silver mixed metal, etc.), rare earth metals (indium, Ytterbium etc.).
- the hole injection layer and the hole transport layer of the light emitting device of the present invention have any one of a function of injecting holes from the anode, a function of transporting holes, and a function of blocking electrons injected from the cathode. If it is, These layer materials include carbazole derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, styryl.
- Anthracene derivatives fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidin compounds, porphyrin compounds, polysilane compounds, poly (N-vinylcarbazole) derivatives, Examples thereof include polymers containing these, such as organosilane derivatives.
- conductive polymer oligomers such as aniline-based copolymers, thiophene oligomers, and polythiophenes can be used. These materials may be one component alone or a plurality of components may be used in combination.
- the hole injection layer and the hole transport layer may have a single layer structure composed of one or more of the materials, or a multilayer structure composed of a plurality of layers having the same composition or different compositions. May be.
- the electron injection layer and the electron transport layer of the light emitting device of the present invention have any one of a function of injecting electrons from the cathode, a function of transporting electrons, and a function of blocking holes injected from the anode. I just need it.
- These layer materials include triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, fluorenone derivatives, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimide derivatives, fluorenylidene.
- Typical examples include metal complexes of methane derivatives, distyrylpyrazine derivatives, aromatic ring tetracarboxylic anhydrides such as naphthalene and perylene, phthalocyanine derivatives, 8-quinolinol derivatives, metal phthalocyanine, benzoxazole and benzothiazole. And various metal complexes, organosilane derivatives, and the like.
- the electron injection layer and the electron transport layer may have a single layer structure composed of one or more of the materials, or a multilayer structure composed of a plurality of layers having the same composition or different compositions. Good.
- an insulator or a semiconductor inorganic compound can also be used as the material for the electron injection layer and the electron transport layer. If the electron injection layer and the electron transport layer are made of an insulator or a semiconductor, current leakage can be effectively prevented and the electron injection property can be improved.
- an insulator at least one metal compound selected from the group consisting of alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides, and alkaline earth metal halides can be used.
- Preferred alkali metal chalcogenides include CaO, BaO, SrO, BeO, BaS, and CaSe.
- the semiconductor constituting the electron injection layer and the electron transport layer is selected from the group consisting of Ba, Ca, Sr, Yb, Al, Ga, In, Li, Na, Cd, Mg, Si, Ta, Sb and Zn. And oxides, nitrides, oxynitrides, and the like containing at least one kind of element. These oxides, nitrides, and oxynitrides may be used alone or in combination of two or more.
- a reducing dopant may be added to the interface region with the thin film in contact with the cathode.
- Reducing dopants include alkali metals, alkaline earth metal oxides, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal Preference is given to at least one compound selected from the group consisting of halides, rare earth metal oxides, rare earth metal halides, alkali metal complexes, alkaline earth metal complexes and rare earth metal complexes.
- the light emitting layer of the light emitting device of the present invention can inject holes from an anode or a hole injection layer when a voltage is applied, and can inject electrons from a cathode or an electron injection layer. It has a function of moving holes) by the force of an electric field, a field of recombination of electrons and holes, and a function of connecting this to light emission.
- the light emitting layer of the light emitting device of the present invention preferably contains at least the metal complex and the organic compound, and may contain a host material using the metal complex and the organic compound as a guest material.
- Examples of the host material include those having a fluorene skeleton, those having a carbazole skeleton, those having a diarylamine skeleton, those having a pyridine skeleton, those having a pyrazine skeleton, those having a triazine skeleton, and having an arylsilane skeleton And the like.
- the host material T1 (energy level of the lowest triplet excited state) is preferably larger than that of the guest material, and more preferably the difference is larger than 0.2 eV.
- the host material may be a low molecular compound or a high molecular compound.
- a light-emitting layer in which the host material is doped with the host material can be formed by mixing the host material and a light-emitting material such as the metal complex, or by performing co-evaporation.
- the method for forming each layer includes a vacuum deposition method (resistance heating deposition method, electron beam method, etc.), sputtering method, LB method, molecular lamination method, coating method (casting method, spin coating method, Bar coating method, blade coating method, roll coating method, gravure printing, screen printing, inkjet method, etc.).
- a vacuum deposition method resistance heating deposition method, electron beam method, etc.
- sputtering method LB method
- coating method (casting method, spin coating method, Bar coating method, blade coating method, roll coating method, gravure printing, screen printing, inkjet method, etc.).
- coating method it is preferable to form into a film by application
- the metal complex and the organic compound can be dissolved in a solvent to prepare a coating solution, and the coating solution can be formed on a desired layer (or electrode) by coating and drying.
- the coating solution may contain a resin as a host material and / or a binder, and the resin can be dissolved in a solvent or dispersed.
- a resin for example, polyvinyl carbazole
- a conjugated polymer for example, a polyolefin-based polymer
- polyvinyl chloride polycarbonate, polystyrene, polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, poly (N-vinylcarbazole), hydrocarbon resin, ketone resin, phenoxy resin , Polyamide, ethyl cellulose, vinyl acetate, ABS resin, polyurethane, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, and the like.
- the solution may contain an antioxidant, a viscosity modifier and the like as optional components.
- each layer of the light-emitting element of the present invention varies depending on the type of material and the layer structure, but in general, if the film thickness is too thin, defects such as pinholes are likely to occur. In general, the thickness is preferably several nm to 1 ⁇ m.
- Examples of the use of the light emitting device of the present invention include a planar light source, illumination, light source, sign light source, backlight light source, display device, and printer head.
- a configuration such as a segment type or a dot matrix type can be selected using a known driving technique, a driving circuit, or the like.
- a metal complex (complex 1, 6.94 g, 5.0 mmol), 5-bromo-2-phenylpyridine (7.32 g, 30.0 mmol) and diglyme (43 mL) are weighed, and silver trifluoromethanesulfonate (2.57 g, 10.0 mmol) was added and stirred at 130 ° C. for 14 hours.
- the resulting reaction was filtered off and the solid was dissolved in methylene chloride (1.3 L). This solution was filtered, and the filtrate was concentrated to about 150 mL.
- the precipitated solid was collected by filtration and washed with hexane to obtain a metal complex represented by the above formula (complex 2, 6.35 g, 7.1 mmol).
- LC-MS measurement was performed by the following method.
- the measurement sample was dissolved in chloroform or tetrahydrofuran to a concentration of about 2 mg / mL, and about 1 ⁇ L was injected into LC-MS (manufactured by Agilent Technologies, trade name: 1100LCMSD).
- LC-MS manufactured by Agilent Technologies, trade name: 1100LCMSD.
- ion-exchanged water to which about 0.1% by weight of acetic acid was added and acetonitrile to which about 0.1% by weight of acetic acid was added were used while changing the ratio. Flowed at a flow rate of minutes.
- L-column 2 ODS 3 ⁇ m
- inner diameter 2.1 mm, length 100 mm, particle size 3 ⁇ m was used.
- NMR measurement was performed by the following method. 5 to 10 mg of a measurement sample was dissolved in about 0.5 mL of deuterated chloroform or deuterated dimethyl sulfoxide and measured using NMR (trade name: MERCURY 300, manufactured by Varian, Inc.).
- the organic phase was washed in the order of 65 mL (twice) ion-exchanged water, 65 mL (twice) 3% by weight acetic acid aqueous solution and 65 mL (twice) ion-exchanged water.
- the organic phase was added dropwise to 800 mL of methanol, a precipitate was formed.
- the precipitate was filtered and dried to obtain a solid. This solid was dissolved in 300 mL of toluene, and the solution was passed through a silica gel / alumina column through which toluene was passed in advance.
- polymer 1 The solution was filtered and dried to obtain 3.48 g of a polymer (hereinafter referred to as “polymer 1”).
- the number average molecular weight Mn in terms of polystyrene of the polymer 1 measured under analysis condition 1 was 1.4 ⁇ 10 5
- the weight average molecular weight Mw in terms of polystyrene was 3.7 ⁇ 10 5 .
- polymer 2 The number average molecular weight Mn in terms of polystyrene of the polymer 2 measured under analysis condition 1 was 2.7 ⁇ 10 5 , and the weight average molecular weight Mw in terms of polystyrene was 7.1 ⁇ 10 5 .
- polymer C a polymer (hereinafter referred to as “polymer C”). Obtained.
- the number average molecular weight Mn in terms of polystyrene of the polymer C measured under the analysis condition 1 was 8.8 ⁇ 10 4
- the weight average molecular weight Mw in terms of polystyrene was 3.2 ⁇ 10 5
- the polymer C is the following formula: It is presumed that the repeating unit represented by (1) is 1: 1 (molar ratio).
- polymer 3 a polymer (hereinafter referred to as “polymer 3”).
- the polystyrene equivalent weight average molecular weight Mw of the polymer 3 measured under analysis condition 1 was 4.8 ⁇ 10 5
- the polystyrene equivalent number average molecular weight Mn was 1.8 ⁇ 10 5
- the polymer 3 is the following formula: It is presumed that the polymer has a repeating unit represented by the formula 80:20 (molar ratio).
- the obtained precipitate was dissolved in diethyl ether, washed once with saturated sodium hydrogen carbonate (aq) and twice with water, and 38.6 g (white powder) of compound D purified by distilling off diethyl ether under reduced pressure. Purity 99.44%).
- the compound D was dispersed in methanol, water was added and the precipitate was filtered off, and the precipitate was recrystallized again with glacial acetic acid.
- the resulting mixture was heated to 100 ° C. under a nitrogen atmosphere. Thereto, 2.5 mg of bistriphenylphosphine palladium dichloride was added. To the obtained solution, 9.81 g of a 17.5% by weight aqueous sodium carbonate solution was added dropwise, followed by stirring for 3 hours. Next, 0.043 g of phenylboric acid, 1.3 mg of bistriphenylphosphine palladium dichloride, and 4 mL of toluene, 9.88 g of a 17.5 wt% sodium carbonate aqueous solution were added thereto, followed by stirring at 100 ° C. for 17 hours.
- polymer 4 a polymer (hereinafter referred to as “polymer 4”).
- the number average molecular weight Mn in terms of polystyrene measured under analysis condition 1 of the polymer 4 was 1.7 ⁇ 10 5
- the weight average molecular weight Mw in terms of polystyrene was 4.7 ⁇ 10 5
- the polymer 4 is represented by the following formula: It is estimated that the repeating unit represented by the formula (1) is 85: 10: 5 (molar ratio).
- organic compound F The resulting reaction solution was allowed to cool and then separated, the aqueous phase was removed, and the organic phase was washed and separated in the order of dilute hydrochloric acid and water. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated. The obtained crude product was passed through a silica gel column, and acetonitrile was added to the obtained filtrate. The obtained crystals were dried under reduced pressure to obtain 8.23 g of white crystals (hereinafter referred to as “organic compound F”).
- organic compound F 1 H-NMR (270 MHz / CDCl 3 ): ⁇ 1.39 (s, 27H), 7.52 (d, 6H), 7.65 (d, 6H), 7.79 (d, 6H), 8.82 (d, 6H)
- a glass substrate having an ITO film with a thickness of 150 nm formed by sputtering is formed into a film with a thickness of 65 nm by spin coating using a solution of poly (ethylenedioxythiophene) / polystyrene sulfonic acid (Bayer, trade name: AI4083). And dried on a hot plate at 200 ° C. for 10 minutes. Next, the polymer C was spin-coated in a 0.8% by weight xylene solution to form a film having a thickness of about 20 nm. Thereafter, heat treatment was performed on a hot plate at 180 ° C. for 60 minutes.
- Composition 1 a polymer 1 dissolved in a xylene solvent at a concentration of 1.5% by weight and a metal complex (MC-1) dissolved in a xylene solvent at a concentration of 1.5% by weight were used in a weight ratio. Then, the mixture (hereinafter referred to as “Composition 1”) was prepared by mixing so as to be 92.5: 7.5. Composition 1 was formed into a film by spin coating at a rotational speed of 3000 rpm. The film thickness was about 80 nm. This was dried at 130 ° C. for 10 minutes in a nitrogen gas atmosphere, and then barium was deposited as a cathode at about 5 nm, and then aluminum was deposited at about 80 nm to produce an EL device.
- Composition 1 was prepared by mixing so as to be 92.5: 7.5.
- Composition 1 was formed into a film by spin coating at a rotational speed of 3000 rpm. The film thickness was about 80 nm. This was dried at 130 ° C.
- the metal deposition was started after the degree of vacuum reached 1 ⁇ 10 ⁇ 4 Pa or less.
- EL light emission having a peak at 600 nm derived from the metal complex (MC-1) was obtained from this device.
- the device started to emit light at 2.6 V, showed 1000 cd / m 2 at 5.3 V, and had a maximum luminous efficiency of 22.32 cd / A.
- the quantum chemical calculation program Gaussian 03 was used to optimize the structure of the ground state by the density functional method at the B3LYP level, and the LUMO in the optimized structure
- the absolute values of the energy levels of the LUMO were calculated, the difference between the absolute values of the LUMO energy levels was calculated to be 0.01 eV.
- Example 2 In Example 1, instead of the polymer 1 solution dissolved in the xylene solvent at a concentration of 1.5% by weight, a solution of the polymer 4 dissolved in the xylene solvent at a concentration of 1.0% by weight was used. An EL element was produced in the same manner as in Example 1 except that it was used. When voltage was applied to the obtained EL device, EL light emission having a peak at 600 nm derived from the metal complex (MC-1) was obtained. The device started to emit light at 2.67 V, showed 1000 cd / m 2 at 6.9 V, and had a maximum luminous efficiency of 24.97 cd / A.
- MC-1 metal complex
- the ground state structure was optimized by the density functional method at the B3LYP level using the quantum chemical calculation program Gaussian 03, and the LUMO of the optimized structure was determined.
- the absolute value of the energy level was calculated, the difference between the absolute values of the LUMO energy levels was calculated to be 0.13 eV.
- Example 3 In Example 1, instead of the solution of polymer 1 dissolved at a concentration of 1.5% by weight in a xylene solvent, a solution of polymer 2 dissolved at a concentration of 1.5% by weight in a xylene solvent; In the same manner as in Example 1 except that a solution obtained by mixing a solution of organic compound F dissolved in xylene solvent at a concentration of 1.5% by weight so as to have a weight ratio of 70:30 was used. An EL element was produced. When voltage was applied to the obtained EL device, EL light emission having a peak at 600 nm derived from the metal complex (MC-1) was obtained.
- MC-1 metal complex
- the device started to emit light at 2.94 V, showed 1000 cd / m 2 at 6.2 V, and had a maximum luminous efficiency of 21.31 cd / A.
- a quantum chemical calculation program Gaussian 03 was used to optimize the structure of the ground state by the density functional method at the B3LYP level, and the LUMO of the optimized structure
- the absolute value of the energy level was calculated, the difference between the absolute values of the LUMO energy levels was calculated to be 0.28 eV.
- Example 4 In Example 1, instead of the solution of polymer 1 dissolved at a concentration of 1.5% by weight in a xylene solvent, a solution of polymer 2 dissolved at a concentration of 1.5% by weight in a xylene solvent; In the same manner as in Example 1 except that a solution prepared by mixing a solution of organic compound F dissolved in xylene solvent at a concentration of 1.5% by weight so as to have a weight ratio of 80:20 was used. An EL element was produced. When voltage was applied to the obtained EL device, EL light emission having a peak wavelength of 605 nm derived from the metal complex (MC-1) was obtained. The device started to emit light at 3.01 V, showed 1000 cd / m 2 at 7.14 V, and had a maximum luminous efficiency of 19.39 cd / A.
- MC-1 metal complex
- Example 5 ⁇ Synthesis of metal complex (MC-2) Under a stream of argon, a metal complex (MC-1, 2.03 g, 1.20 mmol) and methylene chloride (200 mL) were weighed in a reaction vessel to dissolve the metal complex. N-bromosuccinimide (221 mg, 1.24 mmol) was added thereto, and the mixture was stirred at room temperature for 4 hours. The solvent was distilled off, and toluene (50 mL) was added to the residue to dissolve it. The obtained toluene solution was purified by silica gel chromatography (developing solvent: toluene).
- the resulting mixture was heated to 100 ° C. under a nitrogen atmosphere. Thereto, 2.0 mg of bistriphenylphosphine palladium dichloride was added. To the obtained solution, 7.83 g of a 17.5% by weight aqueous sodium carbonate solution was added dropwise, followed by stirring for 3 hours. Next, 0.035 g of phenylboric acid, 1.1 mg of bistriphenylphosphine palladium dichloride, 3 mL of toluene, and 7.80 g of a 17.5 wt% aqueous sodium carbonate solution were added, and the mixture was stirred at 100 ° C. for 16 hours.
- the precipitate was filtered and dried to obtain a solid.
- This solid is dissolved in 40 mL of toluene to prepare a solution.
- This solution is passed through a silica gel / alumina column through which toluene has been passed in advance, and the passed eluate is dropped into 600 mL of methanol, resulting in precipitation. It was.
- the precipitate was filtered and dried to obtain 1.68 g of a polymer (hereinafter referred to as “polymer 5”).
- the number average molecular weight Mn in terms of polystyrene measured under analysis condition 2 of the polymer 5 was 2.1 ⁇ 10 4
- the weight average molecular weight Mw in terms of polystyrene was 6.3 ⁇ 10 4 .
- the polymer 5 is the following formula: It is presumed that the repeating unit represented by the formula (1) is 88: 5: 5: 2 (molar ratio).
- the polymer 5 had a residue of a metal complex and a residue of an organic compound, and the absolute values of LUMO energy levels of the metal complex and the organic compound were determined by the following method. Specifically, using the quantum chemistry calculation program Gaussian 03, the structure of the ground state was optimized by the density functional method of the B3LYP level, and the absolute value of the LUMO energy level in the optimized structure was calculated. As a result, the absolute value of the LUMO energy level of the metal complex was calculated to be 2.15 eV, and the absolute value of the LUMO energy level of the organic compound was calculated to be 2.14 eV.
- Example 1 instead of the composition 1, an EL device was prepared in the same manner as in Example 1 except that a solution of the polymer 5 dissolved in a xylene solvent at a concentration of 1.8% by weight was used. Produced. When voltage was applied to the obtained EL device, EL light emission having a peak wavelength of 605 nm derived from the metal complex (MC-2) was obtained. The device started to emit light at 2.70 V, showed 1000 cd / m 2 at 6.2 V, and had a maximum luminous efficiency of 18.38 cd / A.
- MC-2 metal complex
- the ground state structure was optimized by the B3LYP level density functional method using the quantum chemical calculation program Gaussian 03, and the LUMO of the optimized structure was determined.
- the absolute value of the energy level was calculated, the difference in the absolute value of the energy level between LUMO in the organic compound and LUMO derived from the metal complex was calculated to be 0.01 eV.
- Example 1 An EL device was produced in the same manner as in Example 1 except that the polymer 2 was used instead of the polymer 1 in Example 1. When voltage was applied to the obtained EL device, EL light emission having a peak wavelength of 605 nm derived from the metal complex (MC-1) was obtained. The device started to emit light at 3.7 V, showed light emission of 1000 cd / m 2 at 10.3 V, and the maximum light emission efficiency was 9.71 cd / A.
- the quantum chemical calculation program Gaussian 03 was used to optimize the structure of the ground state by the density functional method at the B3LYP level, and the LUMO in the optimized structure
- the difference between the absolute values of the LUMO energy levels was calculated to be 1.15 eV.
- An EL device was produced in the same manner as in Example 1 except that the polymer 3 was used instead of the polymer 1 in Example 1.
- EL light emission having a peak wavelength of 605 nm derived from the metal complex (MC-1) was obtained.
- the device started to emit light at 3.61 V, showed 1000 cd / m 2 at 9.3 V, and had a maximum luminous efficiency of 5.93 cd / A.
- the quantum chemical calculation program Gaussian 03 was used to optimize the structure of the ground state by the density functional method at the B3LYP level, and the LUMO in the optimized structure
- the absolute values of the energy levels of the LUMO were calculated, the difference between the absolute values of the LUMO energy levels was calculated to be 0.77 eV.
- composition of the present invention is particularly useful for the production of light emitting devices such as organic electroluminescence devices.
Abstract
Description
-金属錯体-
本発明の組成物に含有される金属錯体は、前記式(1)で表されるものである。
で表されるもの(即ち、n=0)である。R1、R2、R3、R4、R5、R6、R7、及びR8で表される原子及び基は、具体的には、後述のRとして説明し例示する原子及び基と同じである。但し、化合物の安定性の観点から、前記式(1a)中、mは2又は3であることが好ましい。
前記C1~C12アルコキシフェニル基としては、メトキシフェニル基、エトキシフェニル基、プロピルオキシフェニル基、イソプロピルオキシフェニル基、ブトキシフェニル基、イソブトキシフェニル基、s-ブトキシフェニル基、t-ブトキシフェニル基、ペンチルオキシフェニル基、ヘキシルオキシフェニル基、シクロヘキシルオキシフェニル基、ヘプチルオキシフェニル基、オクチルオキシフェニル基、2-エチルヘキシルオキシフェニル基、ノニルオキシフェニル基、デシルオキシフェニル基、3,7-ジメチルオクチルオキシフェニル基、ラウリルオキシフェニル基等が挙げられる。
前記C1~C12アルキルフェニル基としては、メチルフェニル基、エチルフェニル基、ジメチルフェニル基、プロピルフェニル基、メシチル基、メチルエチルフェニル基、イソプロピルフェニル基、ブチルフェニル基、イソブチルフェニル基、s-ブチルフェニル、t-ブチルフェニル基、ペンチルフェニル基、イソアミルフェニル基、ヘキシルフェニル基、ヘプチルフェニル基、オクチルフェニル基、ノニルフェニル基、デシルフェニル基、ドデシルフェニル基等が挙げられる。
前記C1~C12アルコキシフェノキシ基としては、メトキシフェノキシ基、エトキシフェノキシ基、プロピルオキシフェノキシ基、イソプロピルオキシフェノキシ基、ブトキシフェノキシ基、イソブトキシフェノキシ基、s-ブトキシフェノキシ基、t-ブトキシフェノキシ基、ペンチルオキシフェノキシ基、ヘキシルオキシフェノキシ基、シクロヘキシルオキシフェノキシ基、ヘプチルオキシフェノキシ基、オクチルオキシフェノキシ基、2-エチルヘキシルオキシフェノキシ基、ノニルオキシフェノキシ基、デシルオキシフェノキシ基、3,7-ジメチルオクチルオキシフェノキシ基、ラウリルオキシフェノキシ基等が挙げられる。
前記C1~C12アルキルフェノキシ基としては、メチルフェノキシ基、エチルフェノキシ基、ジメチルフェノキシ基、プロピルフェノキシ基、1,3,5-トリメチルフェノキシ基、メチルエチルフェノキシ基、イソプロピルフェノキシ基、ブチルフェノキシ基、イソブチルフェノキシ基、s-ブチルフェノキシ基、t-ブチルフェノキシ基、ペンチルフェノキシ基、イソアミルフェノキシ基、ヘキシルフェノキシ基、ヘプチルフェノキシ基、オクチルフェノキシ基、ノニルフェノキシ基、デシルフェノキシ基、ドデシルフェノキシ基等が挙げられる。
前記C1~C12アルコキシピリジル基としては、メトキシピリジル基、エトキシピリジル基、プロピルオキシピリジル基、イソプロピルオキシピリジル基、ブトキシピリジル基、イソブトキシピリジル基、s-ブトキシピリジル基、t-ブトキシピリジル基、ペンチルオキシピリジル基、ヘキシルオキシピリジル基、シクロヘキシルオキシピリジル基、ヘプチルオキシピリジル基、オクチルオキシピリジル基、2-エチルヘキシルオキシピリジル基、ノニルオキシピリジル基、デシルオキシピリジル基、3,7-ジメチルオクチルオキシピリジル基、ラウリルオキシピリジル基等が挙げられる。
前記C1~C12アルキルピリジルオキシ基としては、メチルピリジルオキシ基、エチルピリジルオキシ基、ジメチルピリジルオキシ基、プロピルピリジルオキシ基、1,3,5-トリメチルピリジルオキシ基、メチルエチルピリジルオキシ基、イソプロピルピリジルオキシ基、ブチルピリジルオキシ基、イソブチルピリジルオキシ基、s-ブチルピリジルオキシ基、t-ブチルピリジルオキシ基、ペンチルピリジルオキシ基、イソアミルピリジルオキシ基、ヘキシルピリジルオキシ基、ヘプチルピリジルオキシ基、オクチルピリジルオキシ基、ノニルピリジルオキシ基、デシルピリジルオキシ基、ドデシルピリジルオキシ基等が挙げられる。
前記金属錯体は、例えば、配位子となる化合物と金属化合物とを溶液中で反応させることにより合成することができる。必要に応じて、反応系中に塩基、銀塩化合物等が存在していてもよい。また、2-フェニルピリジン誘導体を配位子に有する金属錯体とヘテロ環芳香族化合物とのカップリング反応により、前記金属錯体を合成することができる。
前記有機化合物は、低分子化合物であっても高分子化合物であってもよいが、発光素子に用いた時に発光効率や寿命等の素子特性や成膜性の観点から、ポリスチレン換算の数平均分子量が2×103以上であることが好ましく、2×103~1×108であることがより好ましく、1×104~1×106であることが特に好ましい。なお、本明細書において、ポリスチレン換算の数平均分子量が2×103以上の化合物を高分子化合物といい、他方、単一の組成からなるものを低分子化合物(通常、数平均分子量は2×103未満である。)という。また、前記有機化合物はデンドリマーやオリゴマー等の、低分子化合物と高分子化合物との中間的な構造であるものであってもよい。
で表される2価の基を有する化合物であることがより好ましく、前記式(A)で表される2価の基を有する化合物が前記式(A)で表される2価の基を繰り返し単位として有する高分子化合物であることが特に好ましく、これらにおいてZ6、Z7及びZ8が窒素原子である化合物であることがとりわけ好ましい。
-(Ar2)- (B)
(式中、Ar2は、置換基を有していてもよいアリーレン基、又は置換基を有していてもよい2価の複素環基を表す。)
で表される繰り返し単位を有していてもよい。
で表される基が挙げられる。
で表される基;下記式(3-4)又は下記式(3-5):
で表される基が挙げられ、前記式(3-4)又は前記式(3-5)で表される基が好ましい。
で表される基が好ましい。
で表される繰り返し単位が好ましい。
で表される繰り返し単位が好ましい。
本発明の組成物において、前記金属錯体のLUMOのエネルギーレベルの絶対値と前記有機化合物のLUMOのエネルギーレベルの絶対値との差は0.40eV未満であり、好ましくは0.35eV以下であり、より好ましくは0.30eV以下であるが、発光効率の観点から、前記金属錯体のLUMOのエネルギーが前記有機化合物のLUMOのエネルギーよりも小さいことが望ましい。
1)1種の金属錯体と1種の有機化合物との組み合わせ
金属錯体のLUMOのエネルギーレベルの絶対値と有機化合物のLUMOのエネルギーレベルの絶対値との差が0.40eV未満となる組み合わせ。
2)1種の金属錯体と2種以上の有機化合物との組み合わせ
金属錯体のLUMOのエネルギーレベルの絶対値と、すべての有機化合物の中でLUMOのエネルギーレベルが最大である有機化合物のLUMOのエネルギーレベルの絶対値との差が0.40eV未満となる組み合わせ。
3)2種以上の金属錯体と1種の有機化合物との組み合わせ
すべての金属錯体の中でLUMOのエネルギーレベルが最大である金属錯体のLUMOのエネルギーレベルの絶対値と、有機化合物のLUMOのエネルギーレベルの絶対値との差が0.40eV未満となる組み合わせ。
4)2種以上の金属錯体と2種以上の有機化合物との組み合わせ
すべての金属錯体の中でLUMOのエネルギーレベルが最大である金属錯体のLUMOのエネルギーレベルの絶対値と、すべての有機化合物の中でLUMOのエネルギーレベルが最大である有機化合物のLUMOのエネルギーレベルの絶対値との差が0.40eV未満となる組み合わせ。
1)有機化合物が低分子化合物である場合
TH>TM-0.2(eV)
の関係を満たすことが好ましい。
本発明の化合物は、前記式(1)で表される金属錯体の残基、及び有機化合物の残基を有する化合物であって、計算科学的手法により算出した該金属錯体のLUMOのエネルギーレベルの絶対値と、該有機化合物のLUMOのエネルギーレベルの絶対値との差が0.40eV未満である化合物である。
1.高分子有機化合物の主鎖に金属錯体の残基を有する高分子化合物;
2.高分子有機化合物の末端に金属錯体の残基を有する高分子化合物;
3.高分子有機化合物の側鎖に金属錯体の残基を有する高分子化合物;
等が挙げられる。主鎖に金属錯体の残基を有する場合は、線形高分子の主鎖に金属錯体が組み込まれたものの他に、金属錯体から3個以上の高分子鎖が結合しているものも含まれる。
金属錯体のLUMOのエネルギーレベルの絶対値:金属錯体の残基を有する繰り返し単位の1量体におけるLUMOのエネルギーレベルの絶対値。
有機化合物のLUMOのエネルギーレベルの絶対値:高分子化合物が有するその他の繰り返し単位について考えられる全ての組み合わせについて3量体を形成し、該3量体のLUMOのエネルギーレベルの絶対値を求めたときに、その絶対値が最大となるLUMOのエネルギーレベルの絶対値。
(2)本発明の化合物が金属錯体の残基を末端に有する高分子化合物である場合
金属錯体のLUMOのエネルギーレベルの絶対値:金属錯体の残基における結合手を水素原子に置き換えてなる金属錯体のLUMOのエネルギーレベルの絶対値。
有機化合物のLUMOのエネルギーレベルの絶対値:高分子化合物が有する繰り返し単位について考えられる全ての組み合わせについて3量体を形成し、該3量体のLUMOのエネルギーレベルの絶対値を求めたときに、その絶対値が最大となるLUMOのエネルギーレベルの絶対値。
(3)本発明の化合物が上記(1)、(2)以外である場合
金属錯体のLUMOのエネルギーレベルの絶対値:金属錯体の残基における結合手を水素原子に置き換えてなる金属錯体のLUMOのエネルギーレベルの絶対値。
有機化合物のLUMOのエネルギーレベルの絶対値:化合物中の金属錯体の残基以外の部分において、結合手を水素原子に置き換えてなる有機化合物のLUMOのエネルギーレベルの絶対値。
本発明の素子は、本発明の組成物を用いてなるものであり、例えば、陽極及び陰極からなる電極と、該電極間に設けられ前記金属錯体及び前記有機化合物を含む層とを有する素子である。また、本発明の組成物を用いて膜を形成させ、この膜を用いて本発明の素子を作製することもできる。以下、その代表的なものとして、本発明の素子が発光素子である場合について説明する。
(a)陽極/正孔注入層(正孔輸送層)/発光層/陰極
(b)陽極/発光層/電子注入層(電子輸送層)/陰極
(c)陽極/正孔注入層(正孔輸送層)/発光層/電子注入層(電子輸送層)/陰極
・5-ブロモ-2-フェニルピリジンの合成
反応容器に、2,5-ジブロモピリジン(7.11g、30mmol)、トルエン(130mL)、フェニルホウ酸(4.57g、37.5mmol)、及びテトラキス(トリフェニルホスフィン)パラジウム(0)(1.73g、1.5mmol)を量りとり、窒素気流下、50℃で撹拌しながら反応物を溶解させた。これに2 M 炭酸ナトリウム水溶液(30mL)を加えて、80℃で6時間撹拌した。得られた反応溶液の有機層を回収し、炭酸ナトリウム水溶液及び飽和食塩水で洗浄した。有機層を硫酸ナトリウムで乾燥させ、濾過した後に留去した。この残渣をシリカゲルカラムクロマトグラフィー(ヘキサン/トルエン)で精製し、溶媒を留去して、5-ブロモ-2-フェニルピリジン(6.21g、26.5 mmol)を得た。
反応容器に、金属錯体(complex 1、6.94g、5.0mmol)、5-ブロモ-2-フェニルピリジン(7.32g、30.0mmol)及びジグライム(43mL)を量り取り、トリフルオロメタンスルホン酸銀(2.57g、10.0mmol)を加え、130℃で14時間撹拌した。得られた反応物を濾別し、固体を塩化メチレン(1.3 L)に溶解させた。この溶液を濾過し、濾液を約150mL程度に濃縮した。析出した固体を濾別回収し、ヘキサンで洗浄することにより、上記式で表される金属錯体(complex2、6.35g、7.1mmol)を得た。
LC-MS (positive) m/z : 890 ([M+H]+)
1H NMR (300 MHz, DMSO-d6)
δ 6.51 (d, J = 7.8 Hz, 3 H), δ 6.72 (m, 3 H), δ 6.84 (m, 3 H), δ 7.66 (d, J = 2.0 Hz, 3 H), δ 7.80 (d, J = 7.8 Hz, 3 H), δ 8.05 (dd, J = 2.0, 8.8 Hz, 3 H),δ 8.14 (d, J = 8.8 Hz, 3 H)
LC-MS (positive) m/z : 1072 ([M+K]+)
1H NMR (300 MHz, CDCl3)
δ 1.21 (s, 36 H), δ 6.87 (m, 9 H), δ 7.69 (d, J = 7.7 Hz, 3 H), δ 7.82 (s, 3 H), δ 7.86 (m, 6 H)
LC-MS (APPI, positive) m/z : 380 ([M+H]+)
1H NMR (300 MHz, CDCl3)
δ 1.39 (s, 18 H), δ 7.56 (d, J = 8.4 Hz, 4 H), δ 8.54 (d, J = 8.4 Hz, 4 H)
LC-MS (APCI, positive) m/z : 1686 ([M+H]+)
1H NMR (300 MHz, CDCl3)
δ 1.20 (s, 54 H), δ 6.96 (m, 9 H), δ 7.39 (d, J = 8.4 Hz, 12 H),δ 7.83 (d, J = 7.5 Hz, 3 H),δ 8.18 (d, J = 8.4 Hz, 3 H),δ 8.36 (d, J = 8.4 Hz, 12 H),δ 9.14 (d, J = 8.4 Hz, 3 H),δ 9.33 (s, 3 H)
測定する高分子化合物(重合体)は、約0.05重量%の濃度になるようにテトラヒドロフランに溶解させ、SECに50μL注入した。SECの移動相としてテトラヒドロフランを用い、0.6mL/分の流速で流した。カラムとして、TSKgel SuperHM-H(東ソー製)2本とTSKgel SuperH2000(東ソー製)1本とを直列に繋げて用いた。検出器には示差屈折率検出器(島津製作所製、商品名:RID-10A)を用いた。
測定する高分子化合物(重合体)は、約0.05重量%の濃度になるようにテトラヒドロフランに溶解させ、SECに10μL注入した。SECの移動相としてテトラヒドロフランを用い、2.0mL/minの流速で流した。カラムとして、PLgel MIXED-B(ポリマーラボラトリーズ製)を用いた。検出器にはUV-VIS検出器(島津製作所製:SPD-10Avp)を用いた。
・重合体1の合成
200mLセパラブルフラスコに、9,9-ジオクチルフルオレン-2,7-ジホウ酸エチレングリコールエステル 2.65g(5.0mmol)、9,9-ジオクチル-2,7-ジブロモフルオレン 1.98g(純度96.9%,3.5mmol)、2,4-ビス(4-ブロモフェニル)-6-(4-n-ブチルフェニル)-1,3,5-トリアジン 0.53g(1.0mmol)、N,N’-ビス(4-ブロモフェニル)-N,N’-ビス(2,6-ジメチル-4-tert-ブチルフェニル)-1,4-フェニレンジアミン 0.37g(0.5mmol)、メチルトリオクチルアンモニウムクロリド(商品名:Aliquat336、アルドリッチ社製) 0.65g、及びトルエン 50mLを加えた。窒素雰囲気下、ここに、ビストリフェニルホスフィンパラジウムジクロリド 3.5mgを加え、95℃に加熱した。得られた溶液に、17.5重量%炭酸ナトリウム水溶液 13.5mLを滴下しながら105℃に加熱した後、3時間攪拌した。次に、ここに、フェニルホウ酸 0.61g、ビストリフェニルホスフィンパラジウムジクロリド 3.5mg、及びトルエン50mLを加え、105℃で16時間攪拌した。
得られた溶液から水相を除いた後、そこに、N,N-ジエチルジチオカルバミド酸ナトリウム三水和物 3.04g、及びイオン交換水 30mLを加え、85℃で2時間攪拌した。有機相を水相と分離した後、有機相をイオン交換水 65mL(2回)、3重量%酢酸水溶液 65mL(2回)、イオン交換水 65mL(2回)の順番で洗浄した。
有機相をメタノール 800mLに滴下したところ、沈殿物が生じたので、この沈殿物を濾過、乾燥し、固体を得た。この固体をトルエン 300mLに溶解させ、あらかじめトルエンを通液したシリカゲル/アルミナカラムに溶液を通液し、通液された溶出液をメタノール 1500mLに滴下したところ、沈殿物が生じたので、この沈殿物を濾過、乾燥し、重合体(以下、「重合体1」と言う。)を3.48g得た。分析条件1で測定した重合体1のポリスチレン換算の数平均分子量Mnは1.4×105であり、ポリスチレン換算の重量平均分子量Mwは3.7×105であった。
・重合体2の合成
200mLセパラブルフラスコに、9,9-ジオクチルフルオレン-2,7-ジホウ酸エチレングリコールエステル 3.18g(6.0mmol)、9,9-ジオクチル-2,7-ジブロモフルオレン 3.06g(5.4mmol)、N,N’-ビス(4-ブロモフェニル)-N,N’-ビス(2,6-ジメチル-4-tert-ブチルフェニル)-1,4-フェニレンジアミン 0.44g(0.6mmol)、メチルトリオクチルアンモニウムクロリド(商品名:Aliquat336、アルドリッチ社製) 0.82g、及びトルエン 60mLを加えた。窒素雰囲気下、ここに、ビストリフェニルホスフィンパラジウムジクロリド 4.2mgを加え85℃に加熱した。得られた溶液に、17.5重量%炭酸ナトリウム水溶液 16.3mLを滴下しながら105℃に加熱した後、1.5時間攪拌した。次に、フェニルホウ酸 0.74g、ビストリフェニルホスフィンパラジウムジクロリド 4.2mg、及びトルエン30mLを加え、105℃で17時間攪拌した。
得られた溶液から水相を除いた後、そこに、N,N-ジエチルジチオカルバミド酸ナトリウム三水和物 3.65g、及びイオン交換水 36mLを加え、85℃で2時間攪拌した。有機相を水相と分離した後、有機相をイオン交換水 80mL(2回)、3重量%酢酸水溶液 80mL(2回)、イオン交換水 80mL(2回)の順番で洗浄した。
有機相をメタノール 930mLに滴下したところ、沈殿物が生じたので、この沈殿物を濾過、乾燥し、固体を得た。この固体をトルエン 190mLに溶解させ、あらかじめトルエンを通液したシリカゲル/アルミナカラムに溶液を通液し、通液された溶出液をメタノール 930mLに滴下したところ、沈殿物が生じたので、この沈殿物を濾過後乾燥し、重合体(以下、「重合体2」と言う。)を4.17g得た。分析条件1で測定した重合体2のポリスチレン換算の数平均分子量Mnは2.7×105であり、ポリスチレン換算の重量平均分子量Mwは7.1×105であった。
・重合体Cの合成(正孔輸送性高分子化合物)
ジムロートを接続したフラスコに、下記式:
有機相を水相と分離した後、有機相にトルエン300mlを加えた。有機相を3重量%酢酸水溶液 40ml(2回)、イオン交換水 100ml(1回)の順番で洗浄し、水相と分離した。有機相にN,N-ジエチルジチオカルバミド酸ナトリウム三水和物 0.44g、トルエン 12mlを加え、65℃で、4時間攪拌した。
得られた反応生成物のトルエン溶液を、あらかじめトルエンを通液したシリカゲル/アルミナカラムに通液し、得られた溶液をメタノール 1400mlに滴下したところ、沈殿物が生じたので、この沈殿物を濾過、乾燥し、固体を得た。この固体をトルエン 400mlに溶解させ、メタノール 1400mlに滴下したところ、沈殿物が生じたので、この沈殿物を濾過、乾燥し、重合体(以下、「重合体C」と言う。)を6.33g得た。分析条件1で測定した重合体Cのポリスチレン換算の数平均分子量Mnは8.8×104であり、ポリスチレン換算の重量平均分子量Mwは3.2×105であった。
なお、重合体Cは、仕込み原料から、下記式:
不活性雰囲気下にて、F8-ジホウ酸(2387mg、4.50mmol)、F8-diBr(1505mg、2.70mmol)、F5(ジペンチルフルオレン)-diBr(836mg、1.80mmol)をトルエン(50ml)に溶解させ、45℃に昇温後、酢酸パラジウム(3mg、0.0135mmol)、及びトリスo-メトキシフェニルホスフィン(19mg、0.054mmol)を加え、5分間攪拌した。次いで、32.78重量%ビステトラエチルアンモニウムカーボネート水溶液を(20.2ml)を加え昇温し、約4時間加熱して還流させた。その後、そこに、t-ブチルフェニルボロン酸(401mg)を加え、終夜で加熱して還流させた。得られた反応液を65℃まで冷却した後、5重量%ジエチルジチオカルバミン酸ナトリウム水溶液(50ml)を加えて4時間撹拌し、水層を分液した。再度、反応液に、5重量%ジエチルジチオカルバミン酸ナトリウム水溶液(50ml)を加えて4時間撹拌し、水層を分液した。その後、有機層を、室温まで冷却し、2N塩酸水(100ml)で2回、10重量%酢酸ナトリウム水溶液(100ml)で2回、水(100ml)で6回、洗浄して分液した。得られた有機層を、セライト(100g)を敷き詰めたろ過器に通した後、ろ過器をトルエン(2500ml)で洗浄してトルエン溶液を回収した。トルエン溶液全量を200mlまで濃縮後、それをメタノール(2000ml)に滴下したところ、沈殿が析出したので、その沈殿を濾別した。この沈殿を再度トルエン(200ml)に溶解させた後、得られたトルエン溶液をメタノール(2000ml)に滴下したところ、沈殿が析出したので、その沈殿を濾別した。更に、この沈殿をトルエン(200ml)に溶解させた後、得られたトルエン溶液をメタノール(2000ml)に滴下したところ、沈殿が析出したので、その沈殿を濾別した。得られた沈殿を減圧して乾燥させることにより、重合体(以下、「重合体3」と言う。)を2.55g得た。重合体3の、分析条件1で測定したポリスチレン換算の重量平均分子量Mwは4.8×105であり、ポリスチレン換算の数平均分子量Mnは1.8×105であった。
なお、重合体3は、仕込み原料から、下記式:
・E-1,3-ビス(4-ブロモフェニル)-2-プロペン-1-オン(化合物3)の合成
1H NMR (300MHz, CDCl3); δ(TMS, ppm) 7.90-7.87 (m, 2H, Ar-H), 7.75 (d, j = 1.8Hz, 1H, CH=C), 7.67-7.64 (m, 2H, Ar-H), 7.58-7.52 (m, 4H, Ar-H), 7.47 (d, j = 1.8Hz, 1H, CH=C).
13C NMR (75 MHz, CDCl3);δ(TMS, ppm)144.2, 137.0, 133.9, 132.6, 132.3, 130.3, 130.1, 128.4, 125.4, 122.2.
LC-MS (APPI); m/z=365 [M+H]+.
1H NMR (300MHz, DMSO-d6);δ(TMS, ppm) 9.63 (brs, 2H, NH), 9.44 (brs, 2H, NH), 7.91 (d, j = 8.0 Hz, 2H, Ar-H), 7.45 (d, j = 8.0 Hz, 1H, Ar-H), 2.70 (t, j = 7.5 Hz, 2H, ArCH2-), 2.70 (t, j = 7.5 Hz, 2H, ArCH2-), 1.66-1.56 (m, 2H, ArCH2CH2-), 1.66-1.56 (m, 2H, ArCH2CH2-), 1.30 (brs, 6H, -CH2-), 0.88 (t, j = 6.2 Hz, 3H, -CH3).
13C NMR (75 MHz, DMSO-d6);δ(TMS, ppm)166.2, 149.8, 129.6, 128.9, 125.6, 35.73, 31.79, 31.26, 29.01, 22.79, 14.71.
1H NMR (300MHz, CDCl3);δ(TMS, ppm) 8.54 (d, j = 7.8 Hz, 2H, Ar-H), 8.10 (d, j = 8.4 Hz, 4H, Ar-H), 7.82 (s, 1H, Ar-H), 7.65 (d, j = 8.4 Hz, 4H, Ar-H), 7.32 (d, j = 7.9 Hz, 2H, Ar-H), 2.70 (t, j = 7.6 Hz, 2H, ArCH2-), 1.72-1.62 (m, 2H, ArCH2CH2-), 1.33 (brs, 6H, -CH2-), 0.89 (t, j = 9.2 Hz, 3H, -CH3),
13C NMR (75 MHz, CDCl3);δ(TMS, ppm) 165.1, 163.9, 146.5, 136.5, 135.5, 132.4, 129.0, 128.9, 128.7, 125.8, 109.4, 36.26, 32.04, 31.59, 29.28, 22.94, 14.42.
LC-MS (APPI); m/z=549 [m+h]+.
200mLセパラブルフラスコに、9,9-ジオクチルフルオレン-2,7-ジホウ酸エチレングリコールエステル 1.866g(純度99.9%,3.51mmol)、9,9-ジオクチル-2,7-ジブロモフルオレン 1.392g(純度96.9%,2.46mmol)、4,6-ビス(4-ブロモフェニル)-2-(4-n-ヘキシルフェニル)-ピリミジン 0.389g(純度99.5%,0.70mmol)、N,N’-ビス(4-ブロモフェニル)-N,N’-ビス(2,6-ジメチル-4-tert-ブチルフェニル)-1,4-フェニレンジアミン 0.260g(純度99.9%,0.35mmol)、メチルトリオクチルアンモニウムクロライド(商品名:Aliquat336、アルドリッチ社製) 0.51g及びトルエン 64mLを加えた。得られた混合液を、窒素雰囲気下、100℃に加熱した。そこに、ビストリフェニルホスフィンパラジウムジクロリド 2.5mgを加えた。得られた溶液に、17.5重量%炭酸ナトリウム水溶液 9.81gを滴下した後、3時間攪拌した。次に、そこに、フェニルホウ酸 0.043g、ビストリフェニルホスフィンパラジウムジクロリド 1.3mg、及びトルエン4mL、17.5重量%炭酸ナトリウム水溶液 9.88gを加え、100℃で17時間攪拌した。得られた溶液から水層を除いた後、N,N-ジエチルジチオカルバミド酸ナトリウム三水和物 1.96g、イオン交換水 39mLを加え、85℃で2時間攪拌した。得られた溶液から有機層を水層と分離した後、有機層をイオン交換水 46mL(3回)、3重量%酢酸水溶液 46mL(3回)、イオン交換水 46mL(3回)の順番で洗浄した。得られた有機層をメタノール 600mLに滴下したところ、沈殿が生じた。この沈殿を濾過後、乾燥させて固体を得た。この固体をトルエン 200mLに溶解させて溶液を調製し、あらかじめトルエンを通液したシリカゲル/アルミナカラムにこの溶液を通液し、通液された溶出液をメタノール 1400mLに滴下したところ、沈殿が生じた。この沈殿を濾過後、乾燥させて重合体(以下、「重合体4」と言う。)を2.38g得た。重合体4の、分析条件1で測定したポリスチレン換算の数平均分子量Mnは1.7×105であり、ポリスチレン換算の重量平均分子量Mwは4.7×105であった。
なお、重合体4は、仕込み原料から、下記式:
有機化合物Fの合成
1H-NMR(270MHz/CDCl3):
δ1.39(s、27H)、7.52(d、6H)、7.65(d、6H)、7.79(d、6H)、8.82(d、6H)
スパッタ法により150nmの厚みでITO膜を付けたガラス基板に、ポリ(エチレンジオキシチオフェン)/ポリスチレンスルホン酸の溶液(バイエル社、商品名:AI4083)を用いてスピンコートにより65nmの厚みで成膜し、ホットプレート上で200℃で10分間乾燥した。
次に、重合体Cを0.8重量%のキシレン溶液の状態でスピンコートして、約20nmの厚みに成膜した。その後、ホットプレート上で180℃、60分間熱処理した。
次に、キシレン溶媒中に1.5重量%の濃度で溶解させた重合体1と、1.5重量%の濃度でキシレン溶媒中に溶解させた金属錯体(MC-1)とを、重量比で、92.5:7.5となるように混合して、組成物(以下、「組成物1」と言う。)を調製した。組成物1をスピンコートにより3000rpmの回転速度で成膜した。膜厚は約80nmであった。これを窒素ガス雰囲気下130℃で10分間乾燥した後、陰極としてバリウムを約5nm、次いでアルミニウムを約80nm蒸着して、EL素子を作製した。なお、真空度が、1×10-4Pa以下に到達した後に金属の蒸着を開始した。
得られたEL素子に電圧を印加したところ、この素子から金属錯体(MC-1)に由来する600nmにピークを有するEL発光が得られた。該素子は2.6Vから発光が開始し、5.3Vで1000cd/m2の発光を示し、最大発光効率は22.32cd/Aであった。
なお、前記重合体1及び金属錯体(MC-1)について、量子化学計算プログラムGaussian03を用い、B3LYPレベルの密度汎関数法により、基底状態の構造最適化を行い、該最適化された構造におけるLUMOのエネルギーレベルの絶対値を算出したところ、それらのLUMOのエネルギーレベルの絶対値の差は、0.01eVと算出された。
実施例1において、キシレン溶媒中に1.5重量%の濃度で溶解させた重合体1の溶液に代えて、キシレン溶媒中に1.0重量%の濃度で溶解させた重合体4の溶液を用いた以外は実施例1と同様にして、EL素子を作製した。得られたEL素子に電圧を印加したところ、金属錯体(MC-1)に由来する600nmにピークを有するEL発光が得られた。該素子は2.67Vから発光が開始し、6.9Vで1000cd/m2を示し、最大発光効率は24.97cd/Aであった。
なお、重合体4及び金属錯体(MC-1)について、量子化学計算プログラムGaussian03を用い、B3LYPレベルの密度汎関数法により、基底状態の構造最適化を行い、該最適化された構造におけるLUMOのエネルギーレベルの絶対値を算出したところ、それらのLUMOのエネルギーレベルの絶対値の差は、0.13eVと算出された。
実施例1において、キシレン溶媒中に1.5重量%の濃度で溶解させた重合体1の溶液に代えて、キシレン溶媒中に1.5重量%の濃度で溶解させた重合体2の溶液と、キシレン溶媒中に1.5重量%の濃度で溶解させた有機化合物Fの溶液とを、重量比で70:30となるように混合した溶液を用いた以外は実施例1と同様にして、EL素子を作製した。得られたEL素子に電圧を印加したところ、金属錯体(MC-1)に由来する600nmにピークを有するEL発光が得られた。該素子は2.94Vから発光が開始し、6.2Vで1000cd/m2を示し、最大発光効率は21.31cd/Aであった。
なお、有機化合物E及び金属錯体(MC-1)について、量子化学計算プログラムGaussian03を用い、B3LYPレベルの密度汎関数法により、基底状態の構造最適化を行い、該最適化された構造におけるLUMOのエネルギーレベルの絶対値を算出したところ、それらのLUMOのエネルギーレベルの絶対値の差は、0.28eVと算出された。
実施例1において、キシレン溶媒中に1.5重量%の濃度で溶解させた重合体1の溶液に代えて、キシレン溶媒中に1.5重量%の濃度で溶解させた重合体2の溶液と、キシレン溶媒中に1.5重量%の濃度で溶解させた有機化合物Fの溶液とを、重量比で80:20となるように混合した溶液を用いた以外は実施例1と同様にして、EL素子を作製した。得られたEL素子に電圧を印加したところ、金属錯体(MC-1)に由来するピーク波長605nmを有するEL発光が得られた。該素子は3.01Vから発光が開始し、7.14Vで1000cd/m2を示し、最大発光効率は19.39cd/Aであった。
・金属錯体(MC-2)の合成
金属錯体(MC-2)
LC-MS (APCI,positive) m/z : 1765 ([M+H]+)
1H NMR (300 MHz,CDCl3)
δ 1.20 (s, 54 H), δ 6.85-7.00 (m, 10 H), δ 7.39 (d, J = 7.8 Hz, 12 H), δ 7.83 (d, J = 7.3 Hz, 2 H), δ 7.91 (s, 1 H), δ 8.14 (d, J = 8.8 Hz, 1 H), δ 8.19 (d, J = 8.6 Hz, 2 H), δ 8.36 (d, J = 7.8 Hz, 12 H), δ 9.16 (m, 3 H), δ 9.28 (s, 1 H), δ 9.33 (s, 2 H).
200mLセパラブルフラスコに、9,9-ジオクチルフルオレン-2,7-ジホウ酸エチレングリコールエステル 1.502g(純度99.9%,2.83mmol)、9,9-ジオクチル-2,7-ジブロモフルオレン 1.392g(純度96.9%,2.15mmol)、2,4-ビス(4-ブロモフェニル)-6-(4-n-ヘキシルフェニル)-1,3,5-トリアジン 0.157g(純度99.3%,0.28mmol)、N,N’-ビス(4-ブロモフェニル)-N,N’-ビス(2,6-ジメチル-4-tert-ブチルフェニル)-1,4-フェニレンジアミン 0.209g(純度99.9%,0.28mmol)、金属錯体(MC-2)0.201g(純度99.4%,0.11mmol)、メチルトリオクチルアンモニウムクロライド(商品名:Aliquat336、アルドリッチ社製)0.42g、及びトルエン56mLを加えた。得られた混合液を、窒素雰囲気下、100℃に加熱した。そこに、ビストリフェニルホスフィンパラジウムジクロリド 2.0mgを加えた。得られた溶液に、17.5重量%炭酸ナトリウム水溶液7.83gを滴下した後、3時間攪拌した。次にフェニルホウ酸0.035g、ビストリフェニルホスフィンパラジウムジクロリド1.1mg、トルエン3mL、及び17.5重量%炭酸ナトリウム水溶液7.80gを加え、100℃で16時間攪拌した。
得られた溶液から水層を除いた後、N,N-ジエチルジチオカルバミド酸ナトリウム三水和物1.57g、及びイオン交換水31mLを加え、85℃で2時間攪拌した。得られた溶液から有機層を水層と分離した後、有機層をイオン交換水37mL(3回)、3重量%酢酸水溶液37mL(3回)、イオン交換水37mL(3回)の順番で洗浄した。次いで、有機層をメタノール500mLに滴下したところ、沈殿が生じた。この沈殿を濾過した後、乾燥させて固体を得た。この固体をトルエン40mLに溶解させて溶液を調製し、この溶液を、あらかじめトルエンを通液したシリカゲル/アルミナカラムに通液し、通液された溶出液をメタノール600mLに滴下したところ、沈殿が生じた。この沈殿を濾過した後、乾燥させて重合体(以下、「重合体5」と言う。)を1.68g得た。重合体5の、分析条件2で測定したポリスチレン換算の数平均分子量Mnは2.1×104であり、ポリスチレン換算の重量平均分子量Mwは6.3×104であった。
なお、重合体5は、仕込み原料から、下記式:
なお、重合体5は、金属錯体の残基及び有機化合物の残基を有し、該金属錯体及び該有機化合物のLUMOのエネルギーレベルの絶対値を、以下の方法で求めた。具体的には、量子化学計算プログラムGaussian03を用い、B3LYPレベルの密度汎関数法により、基底状態の構造最適化を行い、該最適化された構造におけるLUMOのエネルギーレベルの絶対値を算出した。その結果、金属錯体のLUMOのエネルギーレベルの絶対値は2.15eV、有機化合物のLUMOのエネルギーレベルの絶対値は2.14eVと算出された。
なお、重合体5及び金属錯体(MC-2)について、量子化学計算プログラムGaussian03を用い、B3LYPレベルの密度汎関数法により、基底状態の構造最適化を行い、該最適化された構造におけるLUMOのエネルギーレベルの絶対値を算出したところ、有機化合物におけるLUMOと金属錯体に由来するLUMOのエネルギーレベルの絶対値の差は、0.01eVと算出された。
実施例1において、重合体1に代えて重合体2を用いた以外は実施例1と同様にして、EL素子を作製した。得られたEL素子に電圧を印加したところ、金属錯体(MC-1)に由来するピーク波長605nmを有するEL発光が得られた。該素子は3.7Vから発光が開始し、10.3Vで1000cd/m2の発光を示し、最大発光効率は9.71cd/Aであった。
なお、前記重合体2及び金属錯体(MC-1)について、量子化学計算プログラムGaussian03を用い、B3LYPレベルの密度汎関数法により、基底状態の構造最適化を行い、該最適化された構造におけるLUMOのエネルギーレベルの絶対値を算出したところ、それらのLUMOのエネルギーレベルの絶対値の差は、1.15eVと算出された。
<比較例2>
実施例1において、重合体1に代えて重合体3を用いた以外は実施例1と同様にして、EL素子を作製した。得られたEL素子に電圧を印加したところ、金属錯体(MC-1)に由来するピーク波長605nmを有するEL発光が得られた。該素子は3.61Vから発光が開始し、9.3Vで1000cd/m2の発光を示し、最大発光効率は5.93cd/Aであった。
なお、前記重合体3及び金属錯体(MC-1)について、量子化学計算プログラムGaussian03を用い、B3LYPレベルの密度汎関数法により、基底状態の構造最適化を行い、該最適化された構造におけるLUMOのエネルギーレベルの絶対値を算出したところ、それらのLUMOのエネルギーレベルの絶対値の差は、0.77eVと算出された。
Claims (23)
- 下記式(1)で表される金属錯体、及び有機化合物を含有する組成物であって、計算科学的手法により算出した該金属錯体の最低非占有分子軌道のエネルギーレベルの絶対値と、該有機化合物の最低非占有分子軌道のエネルギーレベルの絶対値との差が0.40eV未満である組成物。
- 前記Z6~Z8が窒素原子である請求項2又は3に記載の組成物。
- 前記式(A)で表される2価の基を有する化合物が、前記式(A)で表される2価の基を繰り返し単位として有する高分子化合物である請求項3又は4に記載の組成物。
- 前記式(A)で表される2価の基を繰り返し単位として有する高分子化合物が、さらに、下記式(B):
-(Ar2)- (B)
(式中、Ar2は、置換基を有していてもよいアリーレン基、又は置換基を有していてもよい2価の複素環基を表す。)
で表される繰り返し単位を有する請求項5に記載の組成物。 - 前記R7が、前記式(2)で表される基である請求項1~7のいずれか一項に記載の組成物。
- 前記R2及びR7が、前記式(2)で表される基である請求項8に記載の組成物。
- 前記Z1、Z2、Z3、Z4及びZ5において、複数存在する窒素原子が隣接しない組み合わせである請求項1~9のいずれか一項に記載の組成物。
- 前記式(2)で表される基が、下記式(2-1)~(2-8):
で表されるものである請求項1~10のいずれか一項に記載の組成物。 - 前記R2及びR7がそれぞれ独立に、前記式(2-1)又は(2-7)で表される基である請求項11に記載の組成物。
- 前記R2が水素原子であり、前記R7が前記式(2-1)で表される基である請求項11に記載の組成物。
- 前記R2が水素原子であり、前記R7が前記式(2-7)で表される基である請求項11に記載の組成物。
- 前記Mが、白金原子又はイリジウム原子である請求項1~14のいずれか一項に記載の組成物。
- PL発光スペクトルのピーク波長の少なくとも一つが550nm~800nmである燐光発光を示す請求項1~15のいずれか一項に記載の組成物。
- 溶媒又は分散媒を含む請求項1~16のいずれか一項に記載の組成物。
- 下記式(1)で表される金属錯体の残基、及び有機化合物の残基を有する化合物であって、計算科学的手法により算出した該金属錯体の最低非占有分子軌道のエネルギーレベルの絶対値と、該有機化合物の最低非占有分子軌道のエネルギーレベルの絶対値との差が0.40eV未満である化合物。
- 請求項1~18のいずれか一項に記載の組成物を用いてなる膜。
- 請求項1~18のいずれか一項に記載の組成物を用いてなる素子。
- 前記素子が発光素子である請求項20に記載の素子。
- 請求項21に記載の素子を用いた面状光源。
- 請求項21に記載の素子を用いた照明。
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EP20090770140 EP2305772B1 (en) | 2008-06-23 | 2009-06-23 | Composition containing a metal complex and organic compound, and light emitting element using said compound |
CN200980123997.7A CN102066524B (zh) | 2008-06-23 | 2009-06-23 | 含有金属络合物和有机化合物的组合物、以及使用该组合物而成的发光元件 |
US13/000,554 US9048442B2 (en) | 2008-06-23 | 2009-06-23 | Composition containing a metal complex and organic compound, and light-emitting element using said compound |
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Country Status (7)
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US (1) | US9048442B2 (ja) |
EP (1) | EP2305772B1 (ja) |
JP (1) | JP5556063B2 (ja) |
KR (1) | KR101626170B1 (ja) |
CN (1) | CN102066524B (ja) |
TW (1) | TWI493016B (ja) |
WO (1) | WO2009157430A1 (ja) |
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CN102596978A (zh) * | 2009-10-19 | 2012-07-18 | 住友化学株式会社 | 金属络合物、高分子化合物及使用其的元件 |
CN103650194A (zh) * | 2011-05-12 | 2014-03-19 | 剑桥显示技术有限公司 | 有机发光材料和器件 |
CN104031639A (zh) * | 2014-06-25 | 2014-09-10 | 桂林理工大学 | 荧光材料[ZnNa(ehbd)2N3]n及合成方法 |
GB2549246A (en) * | 2015-12-15 | 2017-10-18 | Cambridge Display Tech Ltd | Light-emitting Compound |
WO2020174837A1 (ja) | 2019-02-26 | 2020-09-03 | 住友化学株式会社 | 発光素子 |
US11925102B2 (en) | 2015-06-04 | 2024-03-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
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Cited By (9)
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CN102596978A (zh) * | 2009-10-19 | 2012-07-18 | 住友化学株式会社 | 金属络合物、高分子化合物及使用其的元件 |
CN102596978B (zh) * | 2009-10-19 | 2015-06-17 | 住友化学株式会社 | 金属络合物、高分子化合物及使用其的元件 |
CN103650194A (zh) * | 2011-05-12 | 2014-03-19 | 剑桥显示技术有限公司 | 有机发光材料和器件 |
CN104031639A (zh) * | 2014-06-25 | 2014-09-10 | 桂林理工大学 | 荧光材料[ZnNa(ehbd)2N3]n及合成方法 |
CN104031639B (zh) * | 2014-06-25 | 2015-11-18 | 桂林理工大学 | 荧光材料[ZnNa(ehbd)2N3]n及合成方法 |
US11925102B2 (en) | 2015-06-04 | 2024-03-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
GB2549246A (en) * | 2015-12-15 | 2017-10-18 | Cambridge Display Tech Ltd | Light-emitting Compound |
US11214585B2 (en) | 2015-12-15 | 2022-01-04 | Cambridge Display Technology Limited | Light-emitting composition |
WO2020174837A1 (ja) | 2019-02-26 | 2020-09-03 | 住友化学株式会社 | 発光素子 |
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Publication number | Publication date |
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CN102066524B (zh) | 2014-10-29 |
JP5556063B2 (ja) | 2014-07-23 |
KR101626170B1 (ko) | 2016-05-31 |
KR20110018378A (ko) | 2011-02-23 |
US20110114890A1 (en) | 2011-05-19 |
EP2305772A1 (en) | 2011-04-06 |
US9048442B2 (en) | 2015-06-02 |
EP2305772B1 (en) | 2015-05-20 |
CN102066524A (zh) | 2011-05-18 |
JP2010031246A (ja) | 2010-02-12 |
TWI493016B (zh) | 2015-07-21 |
EP2305772A4 (en) | 2012-08-01 |
TW201009043A (en) | 2010-03-01 |
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