JP6237786B2 - ORGANIC ELECTROLUMINESCENT ELEMENT MATERIAL, ORGANIC ELECTROLUMINESCENT ELEMENT AND LIGHTING DEVICE - Google Patents
ORGANIC ELECTROLUMINESCENT ELEMENT MATERIAL, ORGANIC ELECTROLUMINESCENT ELEMENT AND LIGHTING DEVICE Download PDFInfo
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- JP6237786B2 JP6237786B2 JP2015549032A JP2015549032A JP6237786B2 JP 6237786 B2 JP6237786 B2 JP 6237786B2 JP 2015549032 A JP2015549032 A JP 2015549032A JP 2015549032 A JP2015549032 A JP 2015549032A JP 6237786 B2 JP6237786 B2 JP 6237786B2
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- 239000000463 material Substances 0.000 title claims description 71
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 238000005401 electroluminescence Methods 0.000 claims description 6
- 239000010410 layer Substances 0.000 description 52
- -1 n-octyl group Chemical group 0.000 description 33
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 230000015572 biosynthetic process Effects 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 20
- 238000002347 injection Methods 0.000 description 17
- 239000007924 injection Substances 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000002019 doping agent Substances 0.000 description 9
- 239000003480 eluent Substances 0.000 description 9
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 9
- 238000001228 spectrum Methods 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 238000000576 coating method Methods 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000007639 printing Methods 0.000 description 6
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- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 5
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- 239000012300 argon atmosphere Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 5
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
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- 125000003545 alkoxy group Chemical group 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- 150000001716 carbazoles Chemical class 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 125000000547 substituted alkyl group Chemical group 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- DPZNOMCNRMUKPS-UHFFFAOYSA-N 1,3-Dimethoxybenzene Chemical compound COC1=CC=CC(OC)=C1 DPZNOMCNRMUKPS-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- XHCAGOVGSDHHNP-UHFFFAOYSA-N 1-bromo-4-tert-butylbenzene Chemical compound CC(C)(C)C1=CC=C(Br)C=C1 XHCAGOVGSDHHNP-UHFFFAOYSA-N 0.000 description 2
- XKLNOVWDVMWTOB-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole Chemical compound N1C2=CC=CC=C2C2=C1CCCC2 XKLNOVWDVMWTOB-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
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- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
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- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- 125000004104 aryloxy group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
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- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
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- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Natural products O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 description 2
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- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
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- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
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- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- PFNQVRZLDWYSCW-UHFFFAOYSA-N (fluoren-9-ylideneamino) n-naphthalen-1-ylcarbamate Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1=NOC(=O)NC1=CC=CC2=CC=CC=C12 PFNQVRZLDWYSCW-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- WJYMPXJVHNDZHD-UHFFFAOYSA-N 1,3,5-triethylbenzene Chemical compound CCC1=CC(CC)=CC(CC)=C1 WJYMPXJVHNDZHD-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
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- 238000005286 illumination Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000001989 lithium alloy Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- OLXYLDUSSBULGU-UHFFFAOYSA-N methyl pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC=C1 OLXYLDUSSBULGU-UHFFFAOYSA-N 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229940094933 n-dodecane Drugs 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- NFBOHOGPQUYFRF-UHFFFAOYSA-N oxanthrene Chemical compound C1=CC=C2OC3=CC=CC=C3OC2=C1 NFBOHOGPQUYFRF-UHFFFAOYSA-N 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 229910003445 palladium oxide Inorganic materials 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- GJSGGHOYGKMUPT-UHFFFAOYSA-N phenoxathiine Chemical compound C1=CC=C2OC3=CC=CC=C3SC2=C1 GJSGGHOYGKMUPT-UHFFFAOYSA-N 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 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
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 150000002909 rare earth metal compounds Chemical class 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 150000003967 siloles Chemical class 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 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
- 238000003756 stirring Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-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
- 150000003852 triazoles Chemical class 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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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
- 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
- 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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- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
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- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
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- Optics & Photonics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Description
本件は、カルバゾール骨格を有する有機エレクトロルミネッセンス素子材料、該有機エレクトロルミネッセンス素子材料を含有する有機ルミネッセンス素子、照明装置および表示素子に関する。 The present invention relates to an organic electroluminescence element material having a carbazole skeleton, an organic luminescence element containing the organic electroluminescence element material, an illumination device, and a display element.
有機エレクトロルミネッセンス素子(以下エレクトロルミネッセンスをELと略記することがある)は、電界を印加することより、陽極より注入された正孔と陰極より注入された電子の再結合エネルギーにより発光材料が発光する原理を利用した自発光素子である。
有機エレクトロルミネッセンス素子の発光層では、ホストにドーパントとして発光材料をドーピングするドーピング法が一般的に使用される。ホストの役割として、キャリア輸送層から注入された電荷から効率よく励起子を生成し、ドーパントに励起子を移動させること、ドーパントの役割として、励起子を発光エネルギーに高効率で変換することが求められる。近年では、高効率発光の観点から、りん光ドーパントが盛んに開発され、りん光ドーパントに好適なホスト材料の探索が続いている。
ホスト材料としては、古くから使用されている代表的な骨格としてカルバゾール骨格があり、例えば特許文献1が挙げられ、近年ではキャリアバランスや耐久性向上のため、特許文献2、特許文献3、特許文献4に開示されているように2量体化などが検討されている。In an organic electroluminescence element (hereinafter, electroluminescence may be abbreviated as EL), a light emitting material emits light by recombination energy of holes injected from an anode and electrons injected from a cathode by applying an electric field. It is a self-luminous element utilizing the principle.
In a light emitting layer of an organic electroluminescence element, a doping method is generally used in which a host is doped with a light emitting material as a dopant. As the host, it is necessary to efficiently generate excitons from the charge injected from the carrier transport layer, transfer the excitons to the dopant, and as the dopant, convert the excitons to emission energy with high efficiency. It is done. In recent years, phosphorescent dopants have been actively developed from the viewpoint of high-efficiency light emission, and search for host materials suitable for phosphorescent dopants has continued.
As a host material, there is a carbazole skeleton as a typical skeleton that has been used for a long time. For example, Patent Document 1 is cited. In recent years, Patent Document 2, Patent Document 3, and Patent Document have been proposed to improve carrier balance and durability. Dimerization or the like has been studied as disclosed in FIG.
一方、有機EL素子の大型化、低価格化、更にはフレキシブルディスプレイを展開するために、印刷法(プリンテッドエレクトロニクス)による有機EL素子の製造方法が検討されている。従来の蒸着法ではなく、有機EL材料をインキ化し、塗布することで素子を形成するには、良好な溶剤溶解性が必要である。 On the other hand, in order to increase the size and cost of organic EL elements and to develop flexible displays, a method for manufacturing organic EL elements by a printing method (printed electronics) has been studied. In order to form an element by making an organic EL material into an ink and applying it instead of a conventional vapor deposition method, good solvent solubility is required.
特許文献2、特許文献3、および特許文献4に記載の3,3’−ビスカルバゾール誘導体は、リン光ホストとして知られる一方、分子の平面性が大きいため、共役長が大きくなり、三重項エネルギーの準位が低くなる。故に、三重項エネルギーがドーパントからホストへ逆エネルギー移動し、ホストから無放射失活しうるため、良好な発光特性が得られない。さらに、分子の対称性が高いため、溶剤溶解性が乏しく、印刷法に適用することが難しい。
従って、本発明の課題は、溶剤溶解性に優れるため印刷法での製造に適し、三重項エネルギーが高い故に高効率発光が可能な有機EL材料を提供することである。また、該有機EL材料を用いた有機EL素子、表示素子、及び照明装置を提供することを課題とする。The 3,3′-biscarbazole derivatives described in Patent Document 2, Patent Document 3, and Patent Document 4 are known as phosphorescent hosts, but have a large molecular planarity, resulting in a large conjugate length and triplet energy. The level of becomes low. Therefore, the triplet energy is transferred from the dopant to the host in reverse energy and can be deactivated non-radiatively from the host. Therefore, good emission characteristics cannot be obtained. Furthermore, since the symmetry of the molecule is high, the solvent solubility is poor and it is difficult to apply to the printing method.
Accordingly, an object of the present invention is to provide an organic EL material that is excellent in solvent solubility and suitable for production by a printing method, and that can emit light with high efficiency because of high triplet energy. It is another object of the present invention to provide an organic EL element, a display element, and a lighting device using the organic EL material.
本発明者らは鋭意検討した結果、下記式(1)で表される構造を有することを特徴とする有機EL素子用材料を提供することで、上記課題を解決できることを見出だした。 As a result of intensive studies, the present inventors have found that the above-described problems can be solved by providing an organic EL device material having a structure represented by the following formula (1).
(式(1)中、R1及びR2はそれぞれ独立して水素原子;置換基を有していてもよいアルキル基、アルケニル基、アルキニル基、アリール基、ヘテロアリール基;または重合性反応基を有する基を表す。)(In formula (1), R 1 and R 2 are each independently a hydrogen atom; an optionally substituted alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group; or polymerizable reactive group. Represents a group having
更に、上記有機EL材料を用いることを特徴とする有機EL素子を提供する。 Furthermore, the organic EL element characterized by using the said organic EL material is provided.
更に、上記有機EL素子を有する表示素子及び照明装置を提供する。 Furthermore, the display element and lighting device which have the said organic EL element are provided.
上記式(1)で表される有機EL素子用材料は、カルバゾール間にねじれを有するため三重項エネルギーが大きくなり、ドーパントからホストへの逆エネルギー移動が抑制されるため高効率発光が可能であり、さらに溶剤溶解性に優れることから、印刷法での有機EL素子の製造に好適に利用可能である。 Since the organic EL device material represented by the above formula (1) has a twist between carbazoles, the triplet energy is increased, and the reverse energy transfer from the dopant to the host is suppressed, so that highly efficient light emission is possible. Furthermore, since it is excellent in solvent solubility, it can be suitably used for the production of an organic EL device by a printing method.
〔有機EL素子用材料〕
本発明の有機EL素子用材料は、下記式(1)で表される構造を有することを特徴とする。[Materials for organic EL elements]
The organic EL device material of the present invention has a structure represented by the following formula (1).
(式(1)中、R1及びR2はそれぞれ独立して水素原子;置換基を有していてもよいアルキル基、アルケニル基、アルキニル基、アリール基、ヘテロアリール基;または重合性反応基を有する基を表す。)(In formula (1), R 1 and R 2 are each independently a hydrogen atom; an optionally substituted alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group; or polymerizable reactive group. Represents a group having
本発明の有機EL素子用材料は、上記式(1)で表される1,3‘−ビスカルバゾール構造を有すればよく、上記式(1)で表される構造は1つでも複数でも構わない。 The organic EL device material of the present invention may have a 1,3′-biscarbazole structure represented by the above formula (1), and the structure represented by the above formula (1) may be one or plural. Absent.
本発明の有機EL素子用材料は、2つのカルバゾール間でねじれを有する1,3‘−ビスカルバゾール構造のため、共役長が小さくなり、高い三重項エネルギーを有する。故に、ドーパントからホストへ逆エネルギー移動が生じず、良好な発光特性を得ることが可能となる。本発明の有機EL素子用材料では、高い三重項エネルギー準位を有するため、緑、赤りん光材料に限らず、青りん光材料についてもホスト材料として有効である。また、分子のねじれ構造により、溶剤への溶解性が優れることから、有機EL素子用インクとし、印刷法によって有機EL素子を製造することができる。また、Tgが高いことから、耐熱性に優れる。 Since the organic EL device material of the present invention has a 1,3′-biscarbazole structure having a twist between two carbazoles, the conjugate length is reduced and the triplet energy is high. Therefore, reverse energy transfer does not occur from the dopant to the host, and good light emission characteristics can be obtained. Since the material for an organic EL device of the present invention has a high triplet energy level, not only green and red phosphorescent materials but also blue phosphorescent materials are effective as host materials. Moreover, since the solubility in a solvent is excellent due to the twisted structure of the molecule, the organic EL element can be produced by a printing method using an ink for an organic EL element. Moreover, since Tg is high, it is excellent in heat resistance.
式(1)で表される1,3‘−ビスカルバゾール構造としては、式(1)中、R1及びR2はそれぞれ独立して水素原子;置換基を有していてもよいアルキル基、アルケニル基、アルキニル基、アリール基、ヘテロアリール基;または重合性反応基を有する基を表す。As the 1,3′-biscarbazole structure represented by the formula (1), in the formula (1), R 1 and R 2 are each independently a hydrogen atom; an alkyl group which may have a substituent, An alkenyl group, an alkynyl group, an aryl group, a heteroaryl group; or a group having a polymerizable reactive group.
本明細書中、「水素」という場合、重水素も含むものとする。 In this specification, the term “hydrogen” includes deuterium.
上記置換基を有していてもよいアルキル基として、例えば、メチル基、エチル基、プロピル基、n−ペンチル基、n−ヘキシル基、n−ヘプチル基、n−オクチル基、n−ノニル基、n−デシル基、n−ウンデシル基、n−ドデシル基、n−トリデシル基、n−テトラデシル基、n−ペンタデシル基、n−ヘキサデシル基、n−ヘプタデシル基、n−オクタデシル基などの直鎖アルキル基、さらにはイソプロピル基、n−ブチル基、イソブチル基、s−ブチル基、t−ブチル基などの分岐アルキル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、シクロオクチル基などの環状アルキル基、などが挙げられる。炭素数1〜10のアルキル基が好適であり、メチル基、エチル基、プロピル基、イソプロピル基、n−ブチル基、イソブチル基、s−ブチル基、t−ブチル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基などが挙げられる。 Examples of the alkyl group that may have a substituent include a methyl group, an ethyl group, a propyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, Linear alkyl groups such as n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl Further, branched alkyl groups such as isopropyl group, n-butyl group, isobutyl group, s-butyl group and t-butyl group, cyclic alkyl groups such as cyclopentyl group, cyclohexyl group, cycloheptyl group and cyclooctyl group, etc. Can be mentioned. An alkyl group having 1 to 10 carbon atoms is preferable, and a methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, cyclopentyl group, cyclohexyl group, cyclohexane A heptyl group etc. are mentioned.
上記置換基を有していてもよいアルケニル基として、例えば、ビニル基、アリル基、ブテニル基、ペンテニル基、ヘキセニル基、ヘプテニル基、オクテニル基、デセニル基、ドデセニル基、テトラデセニル基、ヘキサデセニル基、オクタデセニル基などの直鎖アルケニル基、さらには、メチルペンテニル基などの分岐アルケニル基、シクロヘキセニル基、シクロヘプテニル基、4−メチルシクロヘキセン基などの環状のアルケニル基、などが挙げられる。 Examples of the alkenyl group which may have a substituent include, for example, vinyl group, allyl group, butenyl group, pentenyl group, hexenyl group, heptenyl group, octenyl group, decenyl group, dodecenyl group, tetradecenyl group, hexadecenyl group, octadecenyl group And straight-chain alkenyl groups such as a group, and further branched alkenyl groups such as a methylpentenyl group, cyclic alkenyl groups such as a cyclohexenyl group, a cycloheptenyl group, and a 4-methylcyclohexene group.
上記置換基を有してもよいアルキニル基として、例えば、エテニル基、1−プロペニル基、2−プロペニル基、1−ブテニル基、1−ペンテニル基、1−ヘキセニル基、1−ヘプテニル基、1−オクテニル基、1−ノネニル基、1−デセニル基、1−ウンタデセニル基、1−ドデセニル基、1−トリデセニル基、1−テトラデセニル基、1−ペンタデセニル基、1−ヘキサデセニル基、1−ヘプタデセニル基、1−オクタデセニル基、1−ノナデセニル基などが挙げられる。 Examples of the alkynyl group which may have a substituent include, for example, an ethenyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 1-pentenyl group, a 1-hexenyl group, a 1-heptenyl group, 1- Octenyl group, 1-nonenyl group, 1-decenyl group, 1-undecenyl group, 1-dodecenyl group, 1-tridecenyl group, 1-tetradecenyl group, 1-pentadecenyl group, 1-hexadecenyl group, 1-heptadecenyl group, 1- Examples include an octadecenyl group and a 1-nonadecenyl group.
置換基を有してもよいアリール基として、例えば、フェニル基、ビフェニル基、ターフェニル基、ナフチル基、アントラニル基、フェナンスリル基、ピレニル基、クリセニル基、フルオレニル基、9,9−ジメチルフルオレニル基、スピロフルオレニル基、フルオランテニル基が挙げられ、置換基を有する場合、アルキル基、アルケニル基、アルキニル基、アルコキシ基、アリールオキシ基、ハルゲノ基、シアノ基が好ましい。 Examples of the aryl group which may have a substituent include, for example, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthranyl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a fluorenyl group, and 9,9-dimethylfluorenyl. Group, spirofluorenyl group, and fluoranthenyl group, and when having a substituent, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, a halogeno group, and a cyano group are preferable.
置換基を有してもよいヘテロアリール基として、例えば、チオフェン、チアゾール、フラン、オキサゾール、ピラン、ピロール、イミダゾール、ピラゾール、イソチアゾール、イソオキサゾール、フラザン、トリアゾール、ピリジン、ピラジン、ピリミジン、ピリダジン、トリアジン、ベンゾチオフェン、ベンゾチアゾール、チアントレン、イソベンゾフラン、ベンゾオキサゾール、クロメン、キサンテン、フェノキサチイン、インドリジン、イソインドール、インドール、ベンゾイミダゾール、インダゾール、ベンゾトリアゾール、プリン、キノリジン、イソキノリン、キノリン、フタラジン、ナフチリジン、キノキサリン、キナゾリン、シンノリン、プテリジン、カルバゾール、カルボリン、フェナントリジン、アクリジン、ペリミジン、フェナントロリン、フェナジン、フェノチアジン、フェノキサジン、ジベンゾジオキシンから水素原子を1個除いてできる1価基等が挙げられ、より好ましくは、ピリジン、ピラジン、ピリミジン、ピリダジン、トリアジンから水素原子を1個除いてできる1価基等が挙げられる。ヘテロアリール基が置換基を有する場合、好ましい置換基として、アルキル基、アルケニル基、アルキニル基、アルコキシ基、アリールオキシ基、ハルゲノ基、シアノ基、置換アミノ基、フェニル基、ビフェニル基、ターフェニル基、ナフチル基等が挙げられる。 As the heteroaryl group which may have a substituent, for example, thiophene, thiazole, furan, oxazole, pyran, pyrrole, imidazole, pyrazole, isothiazole, isoxazole, furazane, triazole, pyridine, pyrazine, pyrimidine, pyridazine, triazine , Benzothiophene, benzothiazole, thianthrene, isobenzofuran, benzoxazole, chromene, xanthene, phenoxathiin, indolizine, isoindole, indole, benzimidazole, indazole, benzotriazole, purine, quinolidine, isoquinoline, quinoline, phthalazine, naphthyridine , Quinoxaline, quinazoline, cinnoline, pteridine, carbazole, carboline, phenanthridine, acridine, perimidine Examples include monovalent groups formed by removing one hydrogen atom from phenanthroline, phenazine, phenothiazine, phenoxazine, and dibenzodioxin, and more preferably, one hydrogen atom can be removed from pyridine, pyrazine, pyrimidine, pyridazine, and triazine. A monovalent group etc. are mentioned. When the heteroaryl group has a substituent, preferred substituents include an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, a halogeno group, a cyano group, a substituted amino group, a phenyl group, a biphenyl group, and a terphenyl group. And a naphthyl group.
重合性反応基としては、カチオン重合性反応基とラジカル重合性反応基とが挙げられ、カチオン重合性反応基としては、エポキシ基、オキセタニル基等の環状エーテル基等が挙げられ、ラジカル重合性反応性基としては、ビニル基、(メタ)アクリロイル基、アリル基、スチリル基、マレイミド基等のエチレン性不飽和基等が挙げられる。これらの重合性基は、1,3‘−ビスカルバゾールとの間にアルキレン基、アルキレンオキシ基、アリーレン基、ヘテロアリーレン基等の連結基を有しても構わない。重合性反応基を有する場合、本発明の有機EL素子用材料は硬化性材料となり、活性エネルギー線等で硬化できることから、耐溶剤性や耐久性が向上した塗膜を与えることができる。 Examples of the polymerizable reactive group include a cationic polymerizable reactive group and a radical polymerizable reactive group. Examples of the cationic polymerizable reactive group include a cyclic ether group such as an epoxy group and an oxetanyl group, and a radical polymerizable reaction. Examples of the functional group include ethylenically unsaturated groups such as a vinyl group, a (meth) acryloyl group, an allyl group, a styryl group, and a maleimide group. These polymerizable groups may have a linking group such as an alkylene group, an alkyleneoxy group, an arylene group, or a heteroarylene group between 1,3′-biscarbazole. When it has a polymerizable reactive group, the organic EL device material of the present invention becomes a curable material and can be cured with active energy rays or the like, so that a coating film with improved solvent resistance and durability can be provided.
上記式(1)で表される構造としては、低分子化合物でも高分子化合物でもよい。重合性反応基を有する場合、他のモノマーと反応させて共重合体を形成してもかまわない。上記の置換基の中でも、置換基を有しても良いアリール基、置換基を有しても良いヘテロアリール基、置換基を有しても良いアルキル基が好ましく、発光効率が高くなることから、置換基を有しても良いアリール基、置換基を有しても良いヘテロアリール基がより好ましい。 The structure represented by the above formula (1) may be a low molecular compound or a high molecular compound. When it has a polymerizable reactive group, it may be reacted with another monomer to form a copolymer. Among the above-mentioned substituents, an aryl group that may have a substituent, a heteroaryl group that may have a substituent, and an alkyl group that may have a substituent are preferable, and luminous efficiency is increased. An aryl group which may have a substituent and a heteroaryl group which may have a substituent are more preferable.
上記式(1)で表される構造は、1,2,3,4−テトラヒドロカルバゾールを活性炭中で加熱攪拌、または、1位ハロゲン化カルバゾール誘導体と3位ボロン酸カルバゾール誘導体のカップリング反応などで合成することができる。 The structure represented by the above formula (1) is obtained by heating and stirring 1,2,3,4-tetrahydrocarbazole in activated carbon, or by a coupling reaction of a 1-position halogenated carbazole derivative and a 3-position boronic acid carbazole derivative. Can be synthesized.
上記式(1)で表される構造としては、カルバゾール環の1位、3’位を除く部分(2,3,4,5,6,1’,2’,4’,5’,6’位)には、それぞれ独立して水素原子;置換基を有していてもよいアルキル基、アルケニル基、アルキニル基、アリール基、ヘテロアリール基、アルコキシ基;または重合性反応基を有する基を有することができる。 The structure represented by the above formula (1) includes a portion other than the 1-position and 3′-position of the carbazole ring (2,3,4,5,6,1 ′, 2 ′, 4 ′, 5 ′, 6 ′). Each independently has a hydrogen atom; an optionally substituted alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, alkoxy group; or a group having a polymerizable reactive group. be able to.
置換基を有していてもよいアルキル基、アルケニル基、アルキニル基、アリール基、ヘテロアリール基、アルコキシ基;または重合性反応基を有する基の定義は上述の定義と同様である。 The definition of an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an alkoxy group which may have a substituent; or a group having a polymerizable reactive group is the same as the above definition.
上記式(1)で表される構造としては、カルバゾール環の1位、3’位を除く部分(2,3,4,5,6,1’,2’,4’,5’,6’位)に置換基を修飾する場合、カルバゾール環の1位、3’位を除く部分(2,3,4,5,6,1’,2’,4’,5’,6’位)をハロゲン化することで容易に置換基を修飾できる。置換基を修飾する位置として、合成の容易さの観点から、4位、6位、6’位が好適である。 The structure represented by the above formula (1) includes a portion other than the 1-position and 3′-position of the carbazole ring (2,3,4,5,6,1 ′, 2 ′, 4 ′, 5 ′, 6 ′). When the substituent is modified at the position), the portion (2, 3, 4, 5, 6, 1 ′, 2 ′, 4 ′, 5 ′, 6 ′ position) excluding the 1-position and 3′-position of the carbazole ring Substituents can be easily modified by halogenation. From the viewpoint of ease of synthesis, the 4-position, 6-position and 6'-position are preferred as the position for modifying the substituent.
上記式(1)で表される構造としては、具体例を以下に示すが、これらに限定するものではない。 Specific examples of the structure represented by the above formula (1) are shown below, but are not limited thereto.
本発明の有機EL素子用材料は、有機EL素子の活性層材料として使用できる。なお、活性層とは、有機EL素子の正孔注入層、正孔輸送層、電子ブロック層、発光層、正孔ブロック層、電子輸送層、電子注入層などを意味する。中でも、本発明の有機EL素子材料は、高い三重項準位を有するため、正孔輸送層または発光層に有効であり、特に好ましくは発光層である。 The material for organic EL elements of the present invention can be used as an active layer material for organic EL elements. The active layer means a hole injection layer, a hole transport layer, an electron block layer, a light emitting layer, a hole block layer, an electron transport layer, an electron injection layer, or the like of the organic EL element. Especially, since the organic EL element material of this invention has a high triplet level, it is effective for a positive hole transport layer or a light emitting layer, Especially preferably, it is a light emitting layer.
また、本発明の有機EL素子用材料は、有機EL素子の活性層材料以外にも、電子写真感光体、トランジスタ、太陽電池等の分野においても使用できる。 Moreover, the organic EL device material of the present invention can be used in fields such as an electrophotographic photosensitive member, a transistor, and a solar cell in addition to the active layer material of the organic EL device.
本発明の有機EL素子材料を発光層に用いる場合、ホスト材料として特に好適に用いることができる。この時、発光体としては公知慣用の材料を用いることができるが、三重項準位が大きいことからりん光性発光材料のホスト材料として用いることが好ましい。 When the organic EL device material of the present invention is used for a light emitting layer, it can be particularly suitably used as a host material. At this time, a known and commonly used material can be used as the light emitter, but it is preferably used as a host material of a phosphorescent light emitting material because of its large triplet level.
りん光性発光材料としては、ルテニウム、ロジウム、パラジウム、銀、レニウム、オスミウム、イリジウム、白金及び金から選ばれる少なくともひとつの金属を含む有機金属錯体を用いることができる。 As the phosphorescent light-emitting material, an organometallic complex containing at least one metal selected from ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum, and gold can be used.
好ましいりん光性発光材料としては、Ir等の貴金属元素を中心金属として有するIr(ppy)3等の錯体類、Ir(bt)2・acac3等の錯体類、PtOEt3等の錯体類が挙げられる。これらの錯体類の具体例を以下に示すが、下記の化合物に限定されない。Preferred phosphorescent light emitting materials include complexes such as Ir (ppy) 3 having a noble metal element such as Ir as a central metal, complexes such as Ir (bt) 2 .acac 3 , and complexes such as PtOEt 3. . Specific examples of these complexes are shown below, but are not limited to the following compounds.
前記りん光性発光材料が発光層中に含有される量は、1〜25重量%、好ましくは5〜20重量%の範囲にあることがよい。この場合、ホスト材料としては、本発明の有機EL素子用材料を50重量%以上、好ましくは80〜95重量%の範囲とすることがよい。 The amount of the phosphorescent light emitting material contained in the light emitting layer is 1 to 25% by weight, preferably 5 to 20% by weight. In this case, as the host material, the organic EL device material of the present invention is 50% by weight or more, preferably 80 to 95% by weight.
〔有機EL素子用インク〕
本発明の有機EL素子用材料は、そのまま蒸着材料として使用することもできるが、溶媒溶解性に優れることから、溶媒に溶解させて、有機EL素子用インクとして使用することが好ましい。[Ink for organic EL elements]
The organic EL device material of the present invention can be used as a vapor deposition material as it is, but since it is excellent in solvent solubility, it is preferably dissolved in a solvent and used as an organic EL device ink.
使用する有機溶媒は何を用いても構わず、また2種以上の有機溶媒を混合して用いても良い。具体的には、n−ヘキサン、n−オクタン、n−デカン、n−ドデカンなどの脂肪族系溶媒;シクロヘキサンなどの脂環式系溶媒;ベンゼン、トルエン、クメン、o−キシレン、m−キシレン、p−キシレン、p−シメン、メシチレン、アニソール、2−メチルアニソール、3−メチルアニソール、4−メチルアニソール、2,5−ジメチルアニソール、3,5−ジメトキシトルエン、2,4−ジメチルアニソール、フェネトール、安息香酸メチル、安息香酸エチル、安息香酸プロピル、安息香酸ブチル、1,5−ジメチルテトラリン、n−プロピルベンゼン、n−ブチルベンゼン、n−ペンチルベンゼン、n−ヘキシルベンゼン、シクロヘキシルベンゼン、1,3,5−トリエチルベンゼン、1,3−ジメトキシベンゼン、クロロベンゼン、o−ジクロロベンゼン、トリクロロベンゼン等の芳香族系溶媒;テトラヒドロフラン、ジオキサン、エチレングリコールジエチルエーテル、アニソール、ベンジルエチルエーテル、エチルフェニルエーテル、ジフェニルエーテル、メチルジフェニルエーテル、メチル−t−ブチルエーテル等のエーテル系溶媒;酢酸メチル、酢酸エチル、エチルセロソルブ、プロピレングリコールメチルエーテルアセテート等のエステル系溶媒;メタノール、エタノール、イソプロパノール等のアルコール系溶媒;アセトン、メチルエチルケトン、シクロヘキサノン、2−ヘキサノン、2−ヘプタノン、3−ヘプタノン等のケトン系溶媒;その他ジメチルホルムアミド、ジメチルスルホキシド、ジエチルホルムアミドなどが挙げられるが、これらに限定されることはない。 Any organic solvent may be used, or two or more organic solvents may be mixed and used. Specifically, aliphatic solvents such as n-hexane, n-octane, n-decane and n-dodecane; alicyclic solvents such as cyclohexane; benzene, toluene, cumene, o-xylene, m-xylene, p-xylene, p-cymene, mesitylene, anisole, 2-methylanisole, 3-methylanisole, 4-methylanisole, 2,5-dimethylanisole, 3,5-dimethoxytoluene, 2,4-dimethylanisole, phenetole, Methyl benzoate, ethyl benzoate, propyl benzoate, butyl benzoate, 1,5-dimethyltetralin, n-propylbenzene, n-butylbenzene, n-pentylbenzene, n-hexylbenzene, cyclohexylbenzene, 1,3, 5-triethylbenzene, 1,3-dimethoxybenzene, chlorobenzene Aromatic solvents such as o-dichlorobenzene and trichlorobenzene; ether solvents such as tetrahydrofuran, dioxane, ethylene glycol diethyl ether, anisole, benzyl ethyl ether, ethyl phenyl ether, diphenyl ether, methyl diphenyl ether, and methyl-t-butyl ether; acetic acid Ester solvents such as methyl, ethyl acetate, ethyl cellosolve, propylene glycol methyl ether acetate; alcohol solvents such as methanol, ethanol, isopropanol; ketones such as acetone, methyl ethyl ketone, cyclohexanone, 2-hexanone, 2-heptanone, 3-heptanone System solvents; other examples include, but are not limited to, dimethylformamide, dimethylsulfoxide, and diethylformamide. It is not.
有機EL素子用インクとしては、有機EL素子特性を損なわないものであれば、有機EL素子用材料のほかに他の配合材料を含有していてもよく、例えば公知の正孔注入材料、正孔輸送材料、電子注入材料、電子輸送材料、発光材料、バインダーポリマー等を含有していてもよい。 The organic EL element ink may contain other compounding materials in addition to the organic EL element material as long as the organic EL element characteristics are not impaired. It may contain a transport material, an electron injection material, an electron transport material, a light emitting material, a binder polymer and the like.
有機EL素子用インクを発光層に用いる場合、インク中に本材料のほかに発光材料を含有することができる。発光体としては公知慣用の材料を用いることができるが、本発明の有機EL素子用材料は、三重項準位が大きいことからりん光性発光材料に用いることが好ましい。 When the ink for organic EL elements is used for the light emitting layer, the ink can contain a light emitting material in addition to the present material. Although a well-known and usual material can be used as a light-emitting body, since the organic EL element material of this invention has a large triplet level, it is preferable to use it for a phosphorescent light-emitting material.
りん光性発光材料が有機EL素子用インクに含有される量は、本発明の有機EL素子用材料に対して1〜30重量%、好ましくは5〜25重量%の範囲にあることがよい。この場合、ホスト材料としては、本発明の有機EL素子用材料を50重量%以上、好ましくは75〜95重量%の範囲とすることがよい。 The amount of the phosphorescent light-emitting material contained in the organic EL element ink is 1 to 30% by weight, preferably 5 to 25% by weight, based on the organic EL element material of the present invention. In this case, as the host material, the organic EL device material of the present invention is preferably 50% by weight or more, preferably 75 to 95% by weight.
有機EL素子用インクにおいて、本発明の有機EL素子用材料の配合量としては、有機EL素子用インク中、0.1重量%〜10重量%であればよく、好ましくは0.1重量%〜5.0重量%である。 In the organic EL element ink, the blending amount of the organic EL element material of the present invention may be 0.1 wt% to 10 wt% in the organic EL element ink, preferably 0.1 wt% to 5.0% by weight.
〔有機EL素子〕
有機EL素子の構造としては、特に限定は無いが、一般的には電極の少なくとも1つが透明であるカソード(陰極)とアノード(陽極)との間に、エレクトロルミネセント層(発光層)を含むものである。さらに、1つ以上の電子注入層及び/又は電子輸送層がエレクトロルミネセント層(発光層)とカソードとの間に挿入されているもの、1つ以上の正孔注入層及び/又は正孔輸送層がエレクトロルミネセント層(発光層)とアノードとの間に挿入されているものもある。[Organic EL device]
The structure of the organic EL element is not particularly limited, but generally an electroluminescent layer (light emitting layer) is included between a cathode (cathode) and an anode (anode) in which at least one of the electrodes is transparent. It is a waste. Furthermore, one or more electron injection layers and / or electron transport layers are inserted between the electroluminescent layer (light emitting layer) and the cathode, one or more hole injection layers and / or hole transport In some cases, a layer is inserted between the electroluminescent layer (light emitting layer) and the anode.
アノードは正孔注入層への正孔注入の役割を果たすものであり、通常、アルミニウム、金、銀、ニッケル、パラジウム、白金等の金属、インジウム及び/または、スズの酸化物(ITO)などの金属酸化物、ヨウ化銅などのハロゲン化金属、カーボンブラック、あるいは、ポリ(3−メチルチオフェン、ポリピロール、ポリアニリン等の導電性高分子などにより構成される。 The anode plays a role of hole injection into the hole injection layer and is usually made of metal such as aluminum, gold, silver, nickel, palladium, platinum, indium and / or tin oxide (ITO), etc. It is composed of a metal oxide, a metal halide such as copper iodide, carbon black, or a conductive polymer such as poly (3-methylthiophene, polypyrrole, polyaniline).
カソードは電子輸送層/又は電子注入層をを解して発光層に電子を注入する役割を果たす。カソードとして用いられる材料は、効率よく電子注入を行うために、仕事関数の低い金属が好ましく、スズ、マグネシウム、インジウム、カルシウム、セシウム、アルミニウム、銀等の適当な金属又は、それらの合金が用いられる。具体例としては、マグネシウム−銀合金、マグネシウム−インジウム合金、アルミニウム−リチウム合金等が挙げられる。 The cathode serves to inject electrons into the light emitting layer through the electron transport layer / or electron injection layer. The material used as the cathode is preferably a metal having a low work function in order to efficiently inject electrons, and an appropriate metal such as tin, magnesium, indium, calcium, cesium, aluminum, silver, or an alloy thereof is used. . Specific examples include a magnesium-silver alloy, a magnesium-indium alloy, and an aluminum-lithium alloy.
正孔注入層、正孔輸送層、電子輸送層は任意の有機層となるが、正孔注入層はアノードより正孔輸送層へ正孔を注入する効率を高める目的で使用されるものであり、正孔輸送層および電子輸送層は、それぞれ、正孔、電子を発光層へ移動させる役割を果たすものである。また、電子注入層をカソードと電子輸送層の間に設けることができる。 The hole injection layer, hole transport layer, and electron transport layer can be any organic layer, but the hole injection layer is used for the purpose of increasing the efficiency of injecting holes from the anode into the hole transport layer. The hole transport layer and the electron transport layer serve to move holes and electrons to the light emitting layer, respectively. Further, an electron injection layer can be provided between the cathode and the electron transport layer.
正孔注入材料としては、銅フタロシアニン(CuPc)等のフタロシアニン化合物、ポリアニリン、ポリチオフェン等の有機化合物や、バナジウム酸化物、ルテニウム酸化物、モリブデン酸化物等の金属酸化物が挙げられる。 Examples of the hole injection material include phthalocyanine compounds such as copper phthalocyanine (CuPc), organic compounds such as polyaniline and polythiophene, and metal oxides such as vanadium oxide, ruthenium oxide, and molybdenum oxide.
正孔輸送材料としては、トリアゾール誘導体、オキサジアゾール誘導体、イミダゾール誘導体、ポリアリールアルカン誘導体、ピラゾリン誘導体及びピラゾロン誘導体、フェニレンジアミン誘導体、NPB等のアリールアミン誘導体、アミノ置換カルコン誘導体、オキサゾール誘導体、スチリルアントラセン誘導体、フルオレノン誘導体、ヒドラゾン誘導体、スチルベン誘導体、シラザン誘導体、アニリン系共重合体、また、導電性高分子オリゴマー、特にチオフェンオリゴマー等が挙げられる。 Examples of hole transport materials include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives such as NPB, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene Derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, conductive polymer oligomers, particularly thiophene oligomers, and the like can be given.
電子輸送材料としては、Alq3などの金属錯体、10−ヒドロキシベンゾ[h]キノリンの金属錯体、オキサジアゾール誘導体、ジスチリルビフェニル誘導体、シロール誘導体、3−又は5−ヒドロキシフラボン金属錯体、ベンズオキサゾール金属錯体、ベンゾチアゾール金属錯体、トリスベンズイミダゾリルベンゼンキノキサリン化合物、フェナントロリン誘導体、2−t−ブチル−9,10−N,N’−ジシアノアントラキノンジイミン、n型水素化非晶質炭化シリコン、n型硫化亜鉛、n型セレン化亜鉛などが挙げられる。As the electron transporting material, a metal complex such as Alq 3, 10- hydroxy-benzo [h] quinoline metal complexes, oxadiazole derivatives, distyrylbiphenyl derivatives, silole derivatives, 3- or 5-hydroxyflavone metal complexes, benzoxazole Metal complex, benzothiazole metal complex, trisbenzimidazolylbenzenequinoxaline compound, phenanthroline derivative, 2-t-butyl-9,10-N, N′-dicyanoanthraquinonediimine, n-type hydrogenated amorphous silicon carbide, n-type Examples thereof include zinc sulfide and n-type zinc selenide.
電子注入層としては、アルカリ金属、アルカリ金属錯体、アルカリ金属化合物、アルカリ土類金属、アルカリ土類金属錯体、アルカリ土類金属錯体化合物、希土類金属、希土類金属錯体、及び希土類金属化合物等が挙げられる。 Examples of the electron injection layer include alkali metals, alkali metal complexes, alkali metal compounds, alkaline earth metals, alkaline earth metal complexes, alkaline earth metal complex compounds, rare earth metals, rare earth metal complexes, and rare earth metal compounds. .
本発明の有機EL素子材料を有機EL素子とする場合、公知慣用の蒸着法を用いてもよいが、印刷法等の塗布法を用いることが好ましい。用いられる塗布法として、例えば、浸漬法、スプレーコート法、スピンコート法、ブレードコート法、デイップコート法、キャスト法、ロールコート法、バーコート法、ダイコート法、インクジェット法などの液体滴下法などが挙げられる。 When the organic EL element material of the present invention is an organic EL element, a publicly known vapor deposition method may be used, but a coating method such as a printing method is preferably used. Examples of the coating method used include a dipping method, a spray coating method, a spin coating method, a blade coating method, a dip coating method, a casting method, a roll coating method, a bar coating method, a die coating method, and a liquid dropping method such as an inkjet method. Can be mentioned.
〔表示素子、照明装置〕
本発明の有機EL素子用材料を有する有機EL素子は、耐熱性に優れることから、表示装置や照明装置として好適に使用可能である。表示素子としては、アレイ状に配置された構造からなる表示素子、アノードとカソードがX−Yマトリックス状に配置された表示素子いずれにおいても適用することができ、フルカラーあるいはマルチカラーのパネルへ適用することができる。照明装置としては、モノカラーあるいは調光可能な照明装置へ適用することができる。[Display elements, lighting devices]
Since the organic EL element having the organic EL element material of the present invention is excellent in heat resistance, it can be suitably used as a display device or a lighting device. The display element can be applied to both a display element having a structure arranged in an array and a display element having an anode and a cathode arranged in an XY matrix, and is applied to a full-color or multi-color panel. be able to. The lighting device can be applied to a monochromatic or dimmable lighting device.
以下、実施例により本発明をより詳細に説明するが、本発明はこれら実施例に限定されるものではない。 EXAMPLES Hereinafter, although an Example demonstrates this invention in detail, this invention is not limited to these Examples.
〔合成例1〕化合物1の合成 [Synthesis Example 1] Synthesis of Compound 1
250mL四つ口フラスコに1,2,3,4−テトラヒドロカルバゾール(12g,72mmol)、活性炭(12g)、1,2−ジクロロベンゼン120mLを順次加え、空気を500mL/分で加えながら150℃で15時間反応液を攪拌した。室温まで反応液を冷却した後、反応液をろ過、有機溶媒を減圧除去し、カラムクロマトグラフィーにて精製した。有機溶媒を減圧除去した後、黄色固体(中間体1)3.2g(収率:10%)を得た。 To a 250 mL four-necked flask, 1,2,3,4-tetrahydrocarbazole (12 g, 72 mmol), activated carbon (12 g), 120 mL of 1,2-dichlorobenzene were sequentially added, and air was added at 500 mL / min. The reaction was stirred for hours. After cooling the reaction solution to room temperature, the reaction solution was filtered, the organic solvent was removed under reduced pressure, and the residue was purified by column chromatography. After removing the organic solvent under reduced pressure, 3.2 g (yield: 10%) of a yellow solid (Intermediate 1) was obtained.
アルゴン雰囲気下、200mL三つ口フラスコに中間体1(0.836g, 2.52mmol)、4−ブロモ−N,N’−ジフェニルアニリン(1.95g、6.04mmol)、トリス(ジベンジリデン)ジパラジウム(0.130g, 0.13mmol)、トリ−t−ブチルホスフィン(0.076g, 0.38mmol)、ナトリウム−t−ブトキシド(0.725g, 7.55mmol)、トルエン50mLを順次加え、8時間加熱還流した。室温まで反応液を冷却した後、水を加えて分液ロートにて有機層を回収した。有機溶媒を減圧除去後、シリカゲルクロマトグラフィーにて精製し、白色固体(化合物1)1.03g(収率50%)を得た。
1HNMR(CDCl3、300MHz):δ8.42(s,1H)、8.12(d,1H)、7.75(d,1H)、7.62−7.22(m,34H)、7.10(t,4H)、6.94(t,1H)
MSスペクトル(HPLC−MS(APCI)、溶離液;アセトニトリル:THF:水=6:3:1):m/z:819In a 200 mL three-neck flask under an argon atmosphere, Intermediate 1 (0.836 g, 2.52 mmol), 4-bromo-N, N′-diphenylaniline (1.95 g, 6.04 mmol), tris (dibenzylidene) di Palladium (0.130 g, 0.13 mmol), tri-t-butylphosphine (0.076 g, 0.38 mmol), sodium-t-butoxide (0.725 g, 7.55 mmol), and toluene (50 mL) were sequentially added for 8 hours. Heated to reflux. After cooling the reaction solution to room temperature, water was added and the organic layer was recovered with a separatory funnel. After removing the organic solvent under reduced pressure, the residue was purified by silica gel chromatography to obtain 1.03 g (yield 50%) of a white solid (Compound 1).
1 HNMR (CDCl 3 , 300 MHz): δ 8.42 (s, 1H), 8.12 (d, 1H), 7.75 (d, 1H), 7.62-7.22 (m, 34H), 7 .10 (t, 4H), 6.94 (t, 1H)
MS spectrum (HPLC-MS (APCI), eluent; acetonitrile: THF: water = 6: 3: 1): m / z: 819
〔合成例2〕化合物2の合成 [Synthesis Example 2] Synthesis of Compound 2
100mlナスフラスコに中間体1(6.0g、18.0mmol)、ブロモエタン(4.9g、 45.1mmol)、水酸化カリウム3.3g、アセトン40mLを順次加え、5時間加熱還流した。室温まで反応液を冷却した後、水、トルエンを加えて分液ロートにて有機層を回収した。有機溶媒を減圧除去後、シリカゲルクロマトグラフィーにて精製し、白色固体(化合物2)を3.1g(収率44%)を得た。
1HNMR(CDCl3):δ8.35(s,1H)、8.08(d,1H)、7.67−7.16(m,11H)、6.84(t,1H)、4.41(m,4H)、1.46(m,6H)
MSスペクトル(HPLC−MS(APCI)、溶離液;アセトニトリル:水=8:2):m/z:389Intermediate 1 (6.0 g, 18.0 mmol), bromoethane (4.9 g, 45.1 mmol), potassium hydroxide 3.3 g, and acetone 40 mL were sequentially added to a 100 ml eggplant flask and heated to reflux for 5 hours. After cooling the reaction solution to room temperature, water and toluene were added, and the organic layer was recovered with a separatory funnel. After removing the organic solvent under reduced pressure, the residue was purified by silica gel chromatography to obtain 3.1 g (yield 44%) of a white solid (Compound 2).
1 HNMR (CDCl 3 ): δ 8.35 (s, 1H), 8.08 (d, 1H), 7.67-7.16 (m, 11H), 6.84 (t, 1H), 4.41 (M, 4H), 1.46 (m, 6H)
MS spectrum (HPLC-MS (APCI), eluent; acetonitrile: water = 8: 2): m / z: 389
〔合成例3〕化合物3の合成 [Synthesis Example 3] Synthesis of Compound 3
ブロモエタンの代わりに1−ブロモプロパン(5.5g、45.1mmol)を用いたこと以外は合成例2と同様の操作により、白色固体を0.9g(収率40%)を得た。m/zは416であり、目的物の生成を確認した。
1HNMR(CDCl3、300MHz):δ8.35(s,1H)、8.08(d,1H)、7.67−7.16(m,11H)、6.84(t,1H)、4.27(m,4H)、1.56(m,4H)、0.94(m,6H)
MSスペクトル(HPLC−MS(APCI)、溶離液;アセトニトリル:水=8:2):m/z:4160.9 g (yield 40%) of a white solid was obtained in the same manner as in Synthesis Example 2, except that 1-bromopropane (5.5 g, 45.1 mmol) was used instead of bromoethane. m / z was 416, and the production of the target product was confirmed.
1 HNMR (CDCl 3 , 300 MHz): δ 8.35 (s, 1H), 8.08 (d, 1H), 7.67-7.16 (m, 11H), 6.84 (t, 1H), 4 .27 (m, 4H), 1.56 (m, 4H), 0.94 (m, 6H)
MS spectrum (HPLC-MS (APCI), eluent; acetonitrile: water = 8: 2): m / z: 416
〔合成例4〕化合物4の合成 [Synthesis Example 4] Synthesis of Compound 4
4−ブロモ−N,N’−ジフェニルアニリンの代わりに、2−クロロ−4,6−ジ−p−トリル−1,3,5−トリアジン(0.745g、2.52mmol)を用いた以外は、合成例1と同様の操作により白色固体を0.34g(収率32%)を得た。
1HNMR(CDCl3、300MHz):δ9.31(d,1H)、9.20(m,2H)、9.12(d,1H)、8.67(d,8H)、8.27(s,1H)、8.04(d,1H)、7.80(m,2H)、7.48−7.33(m,13H)、7.03(t,1H)、2.49(s,12H)
MSスペクトル(HPLC−MS(APCI)、溶離液;アセトニトリル:THF:水=6:3:1):m/z:850Except for using 2-chloro-4,6-di-p-tolyl-1,3,5-triazine (0.745 g, 2.52 mmol) instead of 4-bromo-N, N′-diphenylaniline By the same operation as in Synthesis Example 1, 0.34 g (yield 32%) of a white solid was obtained.
1 HNMR (CDCl 3 , 300 MHz): δ 9.31 (d, 1H), 9.20 (m, 2H), 9.12 (d, 1H), 8.67 (d, 8H), 8.27 (s , 1H), 8.04 (d, 1H), 7.80 (m, 2H), 7.48-7.33 (m, 13H), 7.03 (t, 1H), 2.49 (s, 12H)
MS spectrum (HPLC-MS (APCI), eluent; acetonitrile: THF: water = 6: 3: 1): m / z: 850
〔合成例5〕化合物5の合成 [Synthesis Example 5] Synthesis of Compound 5
アルゴン雰囲気下、200mL三つ口フラスコに中間体1(1.0g, 3.01mmol)、ジ−p−トリル−1,3,5−トリアジン(0.89g, 3.01mmol)、トリス(ジベンジリデン)ジパラジウム(0.16g,0.15mmol)、トリ−t−ブチルホスフィン(0.09g, 0.45mmol)、ナトリウム−t−ブトキシド(0.87g, 9.03mmol)、トルエン50mLを順次加え、8時間加熱還流した。室温まで反応液を冷却した後、水を加えて分液ロートにて有機層を回収した。有機溶媒を減圧除去後、シリカゲルクロマトグラフィーにて精製し、中間体2を0.64g(収率36%)を得た。 In an argon atmosphere, a 200 mL three-necked flask was charged with intermediate 1 (1.0 g, 3.01 mmol), di-p-tolyl-1,3,5-triazine (0.89 g, 3.01 mmol), tris (dibenzylidene). ) Dipalladium (0.16 g, 0.15 mmol), tri-t-butylphosphine (0.09 g, 0.45 mmol), sodium-t-butoxide (0.87 g, 9.03 mmol), and toluene 50 mL were sequentially added. Heated to reflux for 8 hours. After cooling the reaction solution to room temperature, water was added and the organic layer was recovered with a separatory funnel. The organic solvent was removed under reduced pressure, and the residue was purified by silica gel chromatography to obtain 0.64 g of Intermediate 2 (yield 36%).
アルゴン雰囲気下、200mL三つ口フラスコに中間体2(0.60g, 1.01mmol)、1−ブロモ4−t−ブチルベンゼン(0.26g, 1.21mmol)、トリス(ジベンジリデン)ジパラジウム(0.052g, 0.05mmol)、トリ−t−ブチルホスフィン(0.031g, 0.15mmol)、ナトリウム−t−ブトキシド(0.292g, 3.04mmol)、トルエン50mLを順次加え、8時間加熱還流した。室温まで反応液を冷却した後、水を加えて分液ロートにて有機層を回収した。有機溶媒を減圧除去後、シリカゲルクロマトグラフィーにて精製し、目的物である化合物5を0.47g(収率64%)を得た。
1HNMR(CDCl3、300MHz):δ8.68(d,4H)、8.34(s,1H)、8.05(d,1H)、7.82−7.16(m,15H)、6.84(t,1H)、2.49(s,6H)、1.35(s,9H)
MSスペクトル(HPLC−MS(APCI)、溶離液;アセトニトリル:THF:水=6:3:1):m/z:724In an argon atmosphere, a 200 mL three-necked flask was charged with Intermediate 2 (0.60 g, 1.01 mmol), 1-bromo-4-t-butylbenzene (0.26 g, 1.21 mmol), tris (dibenzylidene) dipalladium ( 0.052 g, 0.05 mmol), tri-t-butylphosphine (0.031 g, 0.15 mmol), sodium-t-butoxide (0.292 g, 3.04 mmol), and toluene 50 mL were sequentially added, and the mixture was heated under reflux for 8 hours. did. After cooling the reaction solution to room temperature, water was added and the organic layer was recovered with a separatory funnel. After removing the organic solvent under reduced pressure, the residue was purified by silica gel chromatography to obtain 0.47 g (yield: 64%) of the target compound 5.
1 HNMR (CDCl 3 , 300 MHz): δ 8.68 (d, 4H), 8.34 (s, 1H), 8.05 (d, 1H), 7.82-7.16 (m, 15H), 6 .84 (t, 1H), 2.49 (s, 6H), 1.35 (s, 9H)
MS spectrum (HPLC-MS (APCI), eluent; acetonitrile: THF: water = 6: 3: 1): m / z: 724
〔合成例6〕化合物6の合成 [Synthesis Example 6] Synthesis of Compound 6
4−ブロモ−N,N’−ジフェニルアニリンの代わりに1−ブロモ4−t−ブチルベンゼン(1.287g, 6.04mmol)を用いた以外は合成例1と同様の操作により白色固体(化合物6)0.9g(収率60%)を得た。
1HNMR(CDCl3、300MHz):δ8.36(s,1H)、8.08(d,1H)、7.67−7.16(m,19H)、6.84(t,1H)、1.35(s,18H)
MSスペクトル(HPLC−MS(APCI)、溶離液;アセトニトリル):m/z:596A white solid (Compound 6) was prepared in the same manner as in Synthesis Example 1 except that 1-bromo-4-t-butylbenzene (1.287 g, 6.04 mmol) was used instead of 4-bromo-N, N′-diphenylaniline. ) 0.9 g (yield 60%) was obtained.
1 HNMR (CDCl 3 , 300 MHz): δ 8.36 (s, 1H), 8.08 (d, 1H), 7.67-7.16 (m, 19H), 6.84 (t, 1H), 1 .35 (s, 18H)
MS spectrum (HPLC-MS (APCI), eluent; acetonitrile): m / z: 596
〔合成例7〕化合物7の合成 [Synthesis Example 7] Synthesis of Compound 7
4−ブロモ−N,N’−ジフェニルアニリンの代わりに、4−(4−ブロモフェニル)−2,6−ジフェニルピリミジン(2.34g、6.04mmol)を用いた以外は、合成例1と同様の操作により目的物である化合物7を1.1g(収率45%)を得た。
1HNMR(CDCl3、300MHz):δ8.79(m,4H)、8.60(t,4H)、8.47(s,1H)、8.35(m,4H)、8.15(m,3H)、7.95(d,2H)、7.85(d,2H)、7.74−7.51(m,19H)、7.39−7.32(m,4H)、7.01(t,1H)
MSスペクトル(HPLC−MS(APCI)、溶離液;アセトニトリル:THF:水=6:3:1):m/z:946The same as Synthesis Example 1 except that 4- (4-bromophenyl) -2,6-diphenylpyrimidine (2.34 g, 6.04 mmol) was used instead of 4-bromo-N, N′-diphenylaniline. Thus, 1.1 g (yield 45%) of the target compound 7 was obtained.
1 HNMR (CDCl 3 , 300 MHz): δ 8.79 (m, 4H), 8.60 (t, 4H), 8.47 (s, 1H), 8.35 (m, 4H), 8.15 (m 3H), 7.95 (d, 2H), 7.85 (d, 2H), 7.74-7.51 (m, 19H), 7.39-7.32 (m, 4H), 7. 01 (t, 1H)
MS spectrum (HPLC-MS (APCI), eluent; acetonitrile: THF: water = 6: 3: 1): m / z: 946
〔合成例8〕化合物8の合成 [Synthesis Example 8] Synthesis of Compound 8
窒素雰囲気下、200mL三つ口フラスコに化合物6(1.0g、3.01mmol)、N−ブロモスクシンイミド(1.63g、9.18mmol)、ジクロロメタン100mLを順次加え、1時間常温にて攪拌した。反応終了後、有機溶媒を減圧除去し、再結晶にて白色固体(中間体3) 1.23g(収率84%)を得た。 Under a nitrogen atmosphere, Compound 6 (1.0 g, 3.01 mmol), N-bromosuccinimide (1.63 g, 9.18 mmol) and 100 mL of dichloromethane were sequentially added to a 200 mL three-necked flask, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the organic solvent was removed under reduced pressure, and 1.23 g (yield 84%) of a white solid (intermediate 3) was obtained by recrystallization.
アルゴン雰囲気下、200mL三つ口フラスコに中間体3(0.40g、0.48mmol)、9,9’−スピロビフルオレン7−イル−ボロン酸(0.62g、1.73mmol)、炭酸ナトリウム(0.20g、1.92mmol)、テトラキス(トリフェニルホスフィン)パラジウム(0.04g、0.03mmol)、トルエン30mLを順次加え、15分間攪拌した。その後、Aliquat336 1.0重量%水溶液10mL加え、80℃で8時間加熱還流した。室温まで反応液を冷却した後、水を加えて分液ロートにて有機層を回収した。有機溶媒を減圧除去後、シリカゲルクロマトグラフィーにて精製し、白色固体(化合物8)を0.33g(収率45%)を得た。
1HNMR(CDCl3、300MHz):δ7.93(d,2H)、7.87(m,4H)、7.93(d,2H)、7.76(m,3H)、7.68−7.55(m,12H)、7.42−7.27(m、14H)、7.15−6.98(m,14H)、6.87(d,1H)、6.73(m,7H)、6.64(m,4H)、6.55(m,2H)、6.45(d,1H)、6.35(d,1H)、1.55(s,18H)
MSスペクトル(HPLC−MS(APCI)、溶離液;アセトニトリル:THF:水=6:3:1):m/z:1539In an argon atmosphere, a 200 mL three-necked flask was charged with Intermediate 3 (0.40 g, 0.48 mmol), 9,9′-spirobifluoren-7-yl-boronic acid (0.62 g, 1.73 mmol), sodium carbonate ( 0.20 g, 1.92 mmol), tetrakis (triphenylphosphine) palladium (0.04 g, 0.03 mmol), and 30 mL of toluene were sequentially added, and the mixture was stirred for 15 minutes. Thereafter, 10 mL of Aliquat 336 1.0 wt% aqueous solution was added, and the mixture was refluxed at 80 ° C. for 8 hours. After cooling the reaction solution to room temperature, water was added and the organic layer was recovered with a separatory funnel. After removing the organic solvent under reduced pressure, the residue was purified by silica gel chromatography to obtain 0.33 g (yield 45%) of a white solid (Compound 8).
1 HNMR (CDCl 3 , 300 MHz): δ 7.93 (d, 2H), 7.87 (m, 4H), 7.93 (d, 2H), 7.76 (m, 3H), 7.68-7 .55 (m, 12H), 7.42-7.27 (m, 14H), 7.15-6.98 (m, 14H), 6.87 (d, 1H), 6.73 (m, 7H) ), 6.64 (m, 4H), 6.55 (m, 2H), 6.45 (d, 1H), 6.35 (d, 1H), 1.55 (s, 18H)
MS spectrum (HPLC-MS (APCI), eluent; acetonitrile: THF: water = 6: 3: 1): m / z: 1539
〔合成参考例1〕比較化合物1の合成 [Synthesis Reference Example 1] Synthesis of Comparative Compound 1
400mL四つ口フラスコにカルバゾール(10g,59.8mmol)、塩化鉄(III)(38.8g、239.3mmol)、クロロホルム200mLを順次加え、30分常温にて攪拌した。反応終了後、有機溶媒を減圧除去し、得られた固形物を、メタノールを加えて洗浄した。ろ過にて固形物を回収し、その後同様のメタノール洗浄を2回繰り返すことで中間体3(16.7g,収率84%)を得た。 Carbazole (10 g, 59.8 mmol), iron (III) chloride (38.8 g, 239.3 mmol) and chloroform (200 mL) were sequentially added to a 400 mL four-necked flask, and the mixture was stirred at room temperature for 30 minutes. After completion of the reaction, the organic solvent was removed under reduced pressure, and the resulting solid was washed with methanol. The solid was recovered by filtration, and then the same methanol washing was repeated twice to obtain Intermediate 3 (16.7 g, yield 84%).
アルゴン雰囲気下、200mL三つ口フラスコに中間体3(0.50g, 1.50mmol)、4−ブロモ−N,N’−ジフェニルアニリン(1.07g, 3.31mmol)、トリス(ジベンジリデン)ジパラジウム(0.08g, 0.08mmol)、トリ−t−ブチルホスフィン(0.05g, 0.23mmol)、ナトリウム−t−ブトキシド(0.43g, 4.51mmol)、トルエン50mLを順次加え、8時間加熱還流した。室温まで反応液を冷却した後、水を加えて分液ロートにて有機層を回収した。有機溶媒を減圧除去後、シリカゲルクロマトグラフィーにて精製し、白色固体(比較化合物1)を0.47g(収率65%)を得た。
1HNMR(CDCl3、300MHz):δ8.45(d,2H)、8.23(d,2H)、7.79(dd,2H)、7.55−7.43(m,8H)、7.35−7.21(m,26H)、7.11(t,4H)
MSスペクトル(HPLC−MS(APCI)、溶離液;アセトニトリル:THF:水=6:3:1):m/z:819In a 200 mL three-necked flask under an argon atmosphere, Intermediate 3 (0.50 g, 1.50 mmol), 4-bromo-N, N′-diphenylaniline (1.07 g, 3.31 mmol), tris (dibenzylidene) di Palladium (0.08 g, 0.08 mmol), tri-t-butylphosphine (0.05 g, 0.23 mmol), sodium-t-butoxide (0.43 g, 4.51 mmol) and toluene (50 mL) were sequentially added for 8 hours. Heated to reflux. After cooling the reaction solution to room temperature, water was added and the organic layer was recovered with a separatory funnel. After removing the organic solvent under reduced pressure, the residue was purified by silica gel chromatography to obtain 0.47 g (yield 65%) of a white solid (Comparative Compound 1).
1 HNMR (CDCl 3 , 300 MHz): δ 8.45 (d, 2H), 8.23 (d, 2H), 7.79 (dd, 2H), 7.55-7.43 (m, 8H), 7 .35-7.21 (m, 26H), 7.11 (t, 4H)
MS spectrum (HPLC-MS (APCI), eluent; acetonitrile: THF: water = 6: 3: 1): m / z: 819
〔評価方法〕
(1)溶剤溶解性評価
合成した化合物、比較化合物1を用いて2.0重量%トルエン溶液を作製した。溶液を1日放置後に目視にて確認し、化合物が溶解した溶液は○、不溶物が確認された溶液は×とした。〔Evaluation method〕
(1) Solvent solubility evaluation Using the synthesized compound and comparative compound 1, a 2.0 wt% toluene solution was prepared. The solution was visually confirmed after standing for 1 day. The solution in which the compound was dissolved was marked with ◯, and the solution with insoluble matter was marked with x.
(2)有機EL素子特性の評価
<蒸着有機EL素子の作製>
洗浄したITO基板にUV−O3を照射後、正孔注入層としてスピンコートによりPEDOT/PSS(CLEVIOS P VP.AI4083)を45nm成膜し、180℃で15分大気中にて加熱した。その後、5×10−3Pa真空下で正孔輸送層としてHT−1を10nm、発光層にはホスト材料およびドーパント材料(GD−1)をそれぞれ共蒸着により30nm、電子輸送層としてET−1を45nm、電子注入層としてフッ化リチウムを0.5nm、陰極としてアルミニウムを100nm順次成膜した。GD−1の含有量は10wt%とした。陰極まで成膜後、グローブボックスに基板を搬送、ガラス基板にて封止することで有機ELデバイスを作製した。(2) Evaluation of characteristics of organic EL element <Preparation of vapor deposition organic EL element>
After UV-O 3 was irradiated onto the cleaned ITO substrate, a PEDOT / PSS (CLEVIOS P VP.AI4083) film having a thickness of 45 nm was formed by spin coating as a hole injection layer, and heated in the atmosphere at 180 ° C. for 15 minutes. Thereafter, HT-1 is 10 nm as a hole transport layer under a vacuum of 5 × 10 −3 Pa, and a host material and a dopant material (GD-1) are 30 nm by co-evaporation as a light emitting layer, and ET-1 as an electron transport layer. 45 nm, lithium fluoride 0.5 nm as an electron injection layer, and aluminum 100 nm as a cathode. The content of GD-1 was 10 wt%. After film formation up to the cathode, the substrate was transported to a glove box and sealed with a glass substrate to produce an organic EL device.
<塗布有機EL素子の作製>
洗浄したITO基板にUV/O3を照射後、正孔注入層としてスピンコートによりPEDOT/PSSを45nm成膜し、180℃で15分大気中にて加熱した。続いて、HT−2の0.3重量%キシレン溶液を用いてスピンコートにより10nm成膜し、窒素雰囲気下にて200℃で30分間乾燥させた。次に、発光層として、ホスト材料とGD−1とを重量比で9:1で含んだ固形分濃度0.8重量%のトルエン溶液を用いてスピンコートにより30nm成膜し、窒素雰囲気下にて110℃で15分間乾燥させた。その後、5×10−3Pa真空下で電子輸送層としてET−1を45nm、電子注入層としてフッ化リチウムを0.5nm、陰極としてアルミニウムを100nm順次成膜した。陰極まで成膜後、グローブボックスに基板を搬送、ガラス基板にて封止することで有機ELデバイスを作製した。<Production of coated organic EL element>
After the irradiated ITO substrate was irradiated with UV / O 3 , a PEDOT / PSS film having a thickness of 45 nm was formed by spin coating as a hole injection layer and heated in the atmosphere at 180 ° C. for 15 minutes. Subsequently, a 10 nm film was formed by spin coating using a 0.3 wt% xylene solution of HT-2 and dried at 200 ° C. for 30 minutes in a nitrogen atmosphere. Next, as a light emitting layer, a 30 nm film was formed by spin coating using a toluene solution containing a host material and GD-1 at a weight ratio of 9: 1 and having a solid concentration of 0.8% by weight. And dried at 110 ° C. for 15 minutes. Thereafter, under a vacuum of 5 × 10 −3 Pa, ET-1 as an electron transport layer was deposited to 45 nm, lithium fluoride as an electron injection layer was 0.5 nm, and aluminum as a cathode was sequentially deposited to 100 nm. After film formation up to the cathode, the substrate was transported to a glove box and sealed with a glass substrate to produce an organic EL device.
<有機EL素子の評価>
有機EL素子の輝度測定
上記のように作製した有機EL素子を、外部電源に接続して直流電圧を印加し、素子からの発光をトプコン製BM−9にて測光し、得られた輝度、電流値から発光効率を算出した。以下の表に10mA/cm2電流印加時の電圧、発光効率を示した。<Evaluation of organic EL element>
Luminance measurement of organic EL element The organic EL element produced as described above was connected to an external power source, a direct current voltage was applied, and light emission from the element was measured with Topcon BM-9. Luminous efficiency was calculated from the value. The table below shows the voltage and luminous efficiency when 10 mA / cm 2 current was applied.
〔実施例1〜7〕
実施例1〜9で得られた本発明の化合物を、上記の評価方法で評価した結果を表1に記載した。[Examples 1-7]
Table 1 shows the results of evaluation of the compounds of the present invention obtained in Examples 1 to 9 by the above evaluation method.
〔比較例1〜2〕
比較化合物1を使用し、実施例と同様の評価を行った結果を表1に示した。[Comparative Examples 1-2]
Table 1 shows the results of the same evaluation as in Examples using Comparative Compound 1.
表1により本発明の化合物は、蒸着素子、塗布素子の両方で高い発光効率を示すことがわかった。本発明の化合物は、従来の化合物より溶剤溶解性に優れているため、塗布素子の作製に有利であることが分かった。 Table 1 shows that the compound of the present invention exhibits high luminous efficiency in both the vapor deposition element and the coating element. It has been found that the compound of the present invention is advantageous in the production of a coating element because it is superior in solvent solubility than the conventional compound.
本発明の有機EL素子用材料は、有機EL素子に好適に利用可能である。 The material for an organic EL element of the present invention can be suitably used for an organic EL element.
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