JP3762398B2 - イプチセン誘導体を使用する有機発光デバイス - Google Patents
イプチセン誘導体を使用する有機発光デバイス Download PDFInfo
- Publication number
- JP3762398B2 JP3762398B2 JP2003303405A JP2003303405A JP3762398B2 JP 3762398 B2 JP3762398 B2 JP 3762398B2 JP 2003303405 A JP2003303405 A JP 2003303405A JP 2003303405 A JP2003303405 A JP 2003303405A JP 3762398 B2 JP3762398 B2 JP 3762398B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- iptycene
- light emitting
- layer
- transport layer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 230000005525 hole transport Effects 0.000 claims description 21
- 239000010410 layer Substances 0.000 claims 5
- 239000012044 organic layer Substances 0.000 claims 2
- 239000000463 material Substances 0.000 description 41
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 239000000758 substrate Substances 0.000 description 25
- 230000015572 biosynthetic process Effects 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 23
- 239000000243 solution Substances 0.000 description 19
- 229940125904 compound 1 Drugs 0.000 description 16
- 239000002019 doping agent Substances 0.000 description 16
- 238000002347 injection Methods 0.000 description 14
- 239000007924 injection Substances 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 229910007857 Li-Al Inorganic materials 0.000 description 10
- 229910008447 Li—Al Inorganic materials 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 230000008021 deposition Effects 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 229910045601 alloy Inorganic materials 0.000 description 5
- 239000000956 alloy Substances 0.000 description 5
- 229940125898 compound 5 Drugs 0.000 description 5
- 239000007772 electrode material Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 230000002028 premature Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229910000838 Al alloy Inorganic materials 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 3
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 3
- VUUUEDHFRJQSSY-UHFFFAOYSA-N 2-(bromomethyl)-1-[2-(bromomethyl)naphthalen-1-yl]naphthalene Chemical group C1=CC=C2C(C3=C4C=CC=CC4=CC=C3CBr)=C(CBr)C=CC2=C1 VUUUEDHFRJQSSY-UHFFFAOYSA-N 0.000 description 2
- LCKGPYMUELSKFX-UHFFFAOYSA-N 2-iodo-1,3-dimethyl-9h-fluorene Chemical compound C1=CC=C2C(C=C(C(=C3C)I)C)=C3CC2=C1 LCKGPYMUELSKFX-UHFFFAOYSA-N 0.000 description 2
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 2
- QEOMONLJQJASPG-UHFFFAOYSA-N Cc(cc1)ccc1-c1nnc(-c(cc2)ccc2-c2cc(C3c4ccccc4C4c5c3cccc5)c4cc2)[o]1 Chemical compound Cc(cc1)ccc1-c1nnc(-c(cc2)ccc2-c2cc(C3c4ccccc4C4c5c3cccc5)c4cc2)[o]1 QEOMONLJQJASPG-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-YYWVXINBSA-N N,N-dimethylformamide-d7 Chemical class [2H]C(=O)N(C([2H])([2H])[2H])C([2H])([2H])[2H] ZMXDDKWLCZADIW-YYWVXINBSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- NGDCLPXRKSWRPY-UHFFFAOYSA-N Triptycene Chemical class C12=CC=CC=C2C2C3=CC=CC=C3C1C1=CC=CC=C12 NGDCLPXRKSWRPY-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- -1 ester compound Chemical class 0.000 description 2
- 238000005424 photoluminescence Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- UGZHWMAAWCKCTH-UHFFFAOYSA-N (1,3-dimethyl-9h-fluoren-2-yl)boronic acid Chemical compound C1=CC=C2C(C=C(C(=C3C)B(O)O)C)=C3CC2=C1 UGZHWMAAWCKCTH-UHFFFAOYSA-N 0.000 description 1
- XPEIJWZLPWNNOK-UHFFFAOYSA-N (4-phenylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC=C1 XPEIJWZLPWNNOK-UHFFFAOYSA-N 0.000 description 1
- UZPIMCDHIDIMBW-UHFFFAOYSA-N 2,7-diiodo-1,3-dimethyl-9h-fluorene Chemical compound IC1=CC=C2C(C=C(C(=C3C)I)C)=C3CC2=C1 UZPIMCDHIDIMBW-UHFFFAOYSA-N 0.000 description 1
- KDHFKMDVFWYSPT-UHFFFAOYSA-N 2-methyl-1-(2-methylnaphthalen-1-yl)naphthalene Chemical group C1=CC=C2C(C3=C4C=CC=CC4=CC=C3C)=C(C)C=CC2=C1 KDHFKMDVFWYSPT-UHFFFAOYSA-N 0.000 description 1
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 1
- AUAYHUWHLGAVCR-UHFFFAOYSA-N C(C1(C=C2[n]3c(cccc4)c4c4c3cccc4)c3ccccc3C11c3ccccc3C11)=C1C=C2[n]1c(cccc2)c2c2c1cccc2 Chemical compound C(C1(C=C2[n]3c(cccc4)c4c4c3cccc4)c3ccccc3C11c3ccccc3C11)=C1C=C2[n]1c(cccc2)c2c2c1cccc2 AUAYHUWHLGAVCR-UHFFFAOYSA-N 0.000 description 1
- VTLKYMSZYNUTQF-XVVXZDBVSA-N C=C(C(c1c2cccc1)c1c3)/C=C\C=C/C2c1ccc3-c(cc1)ccc1-c1nnc(-c(cc2)ccc2-c2cc(C3c4ccccc4C33c4ccccc4C33)c3cc2)[o]1 Chemical compound C=C(C(c1c2cccc1)c1c3)/C=C\C=C/C2c1ccc3-c(cc1)ccc1-c1nnc(-c(cc2)ccc2-c2cc(C3c4ccccc4C33c4ccccc4C33)c3cc2)[o]1 VTLKYMSZYNUTQF-XVVXZDBVSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- JIEVZWRZFHARIC-UHFFFAOYSA-N Cc1nc(-c2ccc(C(C34c5ccccc5C33)c5c4cccc5)c3c2)nc(-c2ccc(C(c3ccccc3C34)c5c3cccc5)c4c2)n1 Chemical compound Cc1nc(-c2ccc(C(C34c5ccccc5C33)c5c4cccc5)c3c2)nc(-c2ccc(C(c3ccccc3C34)c5c3cccc5)c4c2)n1 JIEVZWRZFHARIC-UHFFFAOYSA-N 0.000 description 1
- BKKVDZVXZJJTGD-UHFFFAOYSA-N Cc1nc(-c2ccc(C3c4ccccc4C4c5c3cccc5)c4c2)nc(-c2cc(C3C(C=CC=C4)=CC44c5ccccc35)c4cc2)n1 Chemical compound Cc1nc(-c2ccc(C3c4ccccc4C4c5c3cccc5)c4c2)nc(-c2cc(C3C(C=CC=C4)=CC44c5ccccc35)c4cc2)n1 BKKVDZVXZJJTGD-UHFFFAOYSA-N 0.000 description 1
- NUGPIZCTELGDOS-QHCPKHFHSA-N N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclopentanecarboxamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CC[C@@H](C=1C=NC=CC=1)NC(=O)C1CCCC1)C NUGPIZCTELGDOS-QHCPKHFHSA-N 0.000 description 1
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- VCMNMHHIXVTWCM-UHFFFAOYSA-N c1cc(C(c2ccccc2C23)c4c2cc(-c2ccncc2)c(-c2ccncc2)c4)c3cc1 Chemical compound c1cc(C(c2ccccc2C23)c4c2cc(-c2ccncc2)c(-c2ccncc2)c4)c3cc1 VCMNMHHIXVTWCM-UHFFFAOYSA-N 0.000 description 1
- FOMCYDAOXUDEEA-UHFFFAOYSA-N c1ccc(C2(C3c4cc(-c5nc(-c6ccc(C(c7ccccc7C78)c9c7cccc9)c8c6)nc(-c6cc(C7c8ccccc8C8c9c7cccc9)c8cc6)n5)ccc4C22)c4c3cccc4)c2c1 Chemical compound c1ccc(C2(C3c4cc(-c5nc(-c6ccc(C(c7ccccc7C78)c9c7cccc9)c8c6)nc(-c6cc(C7c8ccccc8C8c9c7cccc9)c8cc6)n5)ccc4C22)c4c3cccc4)c2c1 FOMCYDAOXUDEEA-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical compound O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
- C07C13/64—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings with a bridged ring system
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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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
- H10K85/60—Organic compounds having low molecular weight
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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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C—CHEMISTRY; METALLURGY
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- C—CHEMISTRY; METALLURGY
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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
- C09K2211/1029—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
- C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with oxygen
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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
- C09K2211/1051—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with sulfur
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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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- 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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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
式(I)により表される化合物は、発光層として直接使用することができ、または発光層がイプチセンホストと発光性ドーパントとを含む場合には、発光性ドーパントのホスト材料として使用することができる。
本発明の、ある好ましい実施形態では、R1〜R6のいずれかまたは全てが、
本発明の好ましい実施形態では、イプチセン誘導体は、
この概要は、本発明の内容を素早く理解することができるよう与えられたものである。本発明は、その好ましい実施形態に関する以下の詳細な記述を、添付図面と併せて参照することによって、より完全に理解することができる。
R1〜R6のいずれかまたは全ては存在しなくてよい。R1〜R6の全てが存在しない場合、イプチセン誘導体は置換されていないトリプチセンである。
さらに、存在する場合は、R1〜R6のいずれかまたは全ては電荷輸送置換基を表すものでよい。そのような電荷輸送置換基が存在することにより、電荷バランスを改善することができ、全デバイス性能を高めることができる。電荷輸送置換基は、正孔輸送基または電子輸送基でよい。本発明の好ましい実施形態で、電荷輸送置換基は、
本発明の好ましい実施形態で、イプチセン誘導体は、
本発明のこの態様で、上述のイプチセン誘導体は、発光層として直接使用することができ、または発光層がイプチセンホストと発光性ドーパントとを含む場合には、発光性ドーパント用のホスト材料として使用することができる。任意の既知の発光性材料は、発光性ドーパントとして使用することができる。当業者なら、所与の発光層内部のホストまたはドーパントの量が総合的な望ましい結果に応じて変わることを容易に理解するであろう。典型的な場合、ドーパントは0.1〜20重量%の量で存在する。
その他の好ましい実施形態では、電荷輸送基は、
本発明での使用に適する正孔輸送基で置換されたイプチセン誘導体は、
本発明での使用に適する電子輸送基で置換されたイプチセン誘導体は、
本発明のこの態様によれば、式(I)により表された化合物は、電荷輸送層として直接使用することができ、または電荷輸送層がホスト材料と電荷輸送ドーパントとを含む場合には、電荷輸送ホスト材料を形成することができる。任意の既知の電荷輸送材料を発光性ドーパントとして使用することができる。当業者なら、所与の電荷輸送層内部のホストまたはドーパントの量が総合的に望ましい結果に応じて変わることが、容易に理解されよう。典型的な場合、ドーパントは0.1〜20重量%の量で存在する。
化合物1、2、3の合成
実施例2
化合物4の合成
実施例3
化合物5の合成
実施例4
化合物6の合成
実施例5
化合物7の合成
実施例6
化合物8の合成
実施例7
化合物9の合成
実施例8
ITO/NPD/化合物1/Bphen/Li−Al/Al OLED
以下に述べる方法に従い、発光性材料として化合物1を使用し、正孔輸送物質としてNPDを使用し、電子輸送物質としてBphenを使用し、電子注入材料としてLi−Al合金を使用し、電極材料としてITOおよびAlを使用して、OLEDを製造した。
上記プロセスによって得られたデバイスの輝度、色、および電流−電圧特性について試験をした。ITO電極を正極(+)に接続し、Alカソードを負極(−)に接続することによって、得られたデバイスに駆動電圧をかけ、それによって光の放出について試験をした結果、青色の均一な光が得られた。以下のデバイスデータが得られた。すなわち、電流密度:8Vで300mA/cm2、輝度:8Vで1380cd/m2、最大外部量子効率:0.4%であり、最大外部電力効率0.45lm/W、CIE色座標は(0.18,0.15)であった。
ITO/NPD/化合物1+化合物5/Bphen/Li−Al/Al OLED
以下に述べる方法に従い、発光性材料として用いる化合物5のホスト材料として化合物1を使用し、正孔輸送物質としてNPDを使用し、電子輸送物質としてBphenを使用し、電子注入材料としてLi−Al合金を使用し、電極材料としてITOおよびAlを使用して、OLEDを製造した。
ITO/NPD/化合物1+1重量%化合物9/Bphen/Li−Al/Al OLED
以下に述べる方法に従い、青色発光性材料として用いられる化合物9のホスト材料として化合物1を使用し、正孔輸送物質としてNPDを使用し、電子輸送物質としてBphenを使用し、電子注入材料としてLi−Al合金を使用し、電極材料としてITOおよびAlを使用して、OLEDを製造した。
ITO/NPD/化合物1+2重量%化合物9/Bphen/Li−Al/Al OLED
以下に述べる方法に従い、青色発光性材料として用いられる化合物9のホスト材料として化合物1を使用し、正孔輸送物質としてNPDを使用し、電子輸送物質としてBphenを使用し、電子注入材料としてLi−Al合金を使用し、電極材料としてITOおよびAlを使用して、OLEDを製造した。
ITO/NPD/化合物2+2重量%化合物9/Bphen/Li−Al/Al OLED
以下に述べる方法に従い、青色発光性材料として用いられる化合物9のホスト材料として化合物2を使用し、正孔輸送物質としてNPDを使用し、電子輸送物質としてBphenを使用し、電子注入材料としてLi−Al合金を使用し、電極材料としてITOおよびAlを使用して、OLEDを製造した。
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DE102008007551A1 (de) | 2008-02-05 | 2009-08-06 | Bayer Materialscience Ag | Metallorganische Gerüstverbindungen auf Basis von Triptycen |
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