TWI452114B - Organic electroluminescent element compounds and organic electroluminescent elements - Google Patents
Organic electroluminescent element compounds and organic electroluminescent elements Download PDFInfo
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- TWI452114B TWI452114B TW098114872A TW98114872A TWI452114B TW I452114 B TWI452114 B TW I452114B TW 098114872 A TW098114872 A TW 098114872A TW 98114872 A TW98114872 A TW 98114872A TW I452114 B TWI452114 B TW I452114B
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- electroluminescence device
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- 150000001875 compounds Chemical class 0.000 title claims description 35
- 239000010410 layer Substances 0.000 claims description 113
- 239000000463 material Substances 0.000 claims description 39
- 238000002347 injection Methods 0.000 claims description 21
- 239000007924 injection Substances 0.000 claims description 21
- -1 nitro, fluorenyl Chemical group 0.000 claims description 21
- 238000005401 electroluminescence Methods 0.000 claims description 20
- 230000005525 hole transport Effects 0.000 claims description 19
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 18
- 239000012044 organic layer Substances 0.000 claims description 12
- 239000002019 doping agent Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000005266 diarylamine group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 239000013078 crystal Substances 0.000 description 10
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 9
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 5
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 3
- 150000004056 anthraquinones Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 2
- YJVKLLJCUMQBHN-UHFFFAOYSA-N 2-pyridin-2-ylpyrimidine Chemical compound N1=CC=CC=C1C1=NC=CC=N1 YJVKLLJCUMQBHN-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- 239000012327 Ruthenium complex Substances 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000004984 aromatic diamines Chemical class 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 description 2
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Natural products O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 229960005181 morphine Drugs 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 150000004866 oxadiazoles Chemical class 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 150000004032 porphyrins Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 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 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- ZYZCALPXKGUGJI-DDVDASKDSA-M (e,3r,5s)-7-[3-(4-fluorophenyl)-2-phenyl-5-propan-2-ylimidazol-4-yl]-3,5-dihydroxyhept-6-enoate Chemical compound C=1C=C(F)C=CC=1N1C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C(C)C)N=C1C1=CC=CC=C1 ZYZCALPXKGUGJI-DDVDASKDSA-M 0.000 description 1
- 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
- KVGZZAHHUNAVKZ-UHFFFAOYSA-N 1,4-Dioxin Chemical compound O1C=COC=C1 KVGZZAHHUNAVKZ-UHFFFAOYSA-N 0.000 description 1
- ZMLPKJYZRQZLDA-UHFFFAOYSA-N 1-(2-phenylethenyl)-4-[4-(2-phenylethenyl)phenyl]benzene Chemical group C=1C=CC=CC=1C=CC(C=C1)=CC=C1C(C=C1)=CC=C1C=CC1=CC=CC=C1 ZMLPKJYZRQZLDA-UHFFFAOYSA-N 0.000 description 1
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 1
- ZVFJWYZMQAEBMO-UHFFFAOYSA-N 1h-benzo[h]quinolin-10-one Chemical compound C1=CNC2=C3C(=O)C=CC=C3C=CC2=C1 ZVFJWYZMQAEBMO-UHFFFAOYSA-N 0.000 description 1
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
- JQPFYXFVUKHERX-UHFFFAOYSA-N 2-hydroxy-2-cyclohexen-1-one Natural products OC1=CCCCC1=O JQPFYXFVUKHERX-UHFFFAOYSA-N 0.000 description 1
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- ZGIKWINFUGEQEO-UHFFFAOYSA-N 3-bromoquinoline Chemical compound C1=CC=CC2=CC(Br)=CN=C21 ZGIKWINFUGEQEO-UHFFFAOYSA-N 0.000 description 1
- 229910001316 Ag alloy Inorganic materials 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- JBMKAUGHUNFTOL-UHFFFAOYSA-N Aldoclor Chemical class C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC=NS2(=O)=O JBMKAUGHUNFTOL-UHFFFAOYSA-N 0.000 description 1
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- KCBAMQOKOLXLOX-BSZYMOERSA-N CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O Chemical compound CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O KCBAMQOKOLXLOX-BSZYMOERSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
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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
- H10K85/649—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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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
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- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
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- C09B57/00—Other synthetic dyes of known constitution
- C09B57/10—Metal complexes of organic compounds not being dyes in uncomplexed form
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
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- 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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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- 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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- 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
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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
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Description
本發明為有關新穎之有機電致發光元件用化合物及使用其之有機電致發光元件(以下，亦稱為有機EL元件)之發明。
一般而言，有機EL元件，其最簡單之構造為由發光層及挾夾該層之一對的對向電極所構成。即，有機EL元件為利用於兩電極間施加電場時，經由陰極注入電子，由陽極注入電洞，使其於發光層中之再鍵結，而以光線方式釋出之現象。
近年來，已開始進行使用有機薄膜之有機EL元件的開發。特別是為提高發光效率、提高電極注入載體之效率之目的，而對電極種類作最適當化之處理，經由開發由芳香族二胺所形成之電洞輸送層與由8-羥基喹啉鋁錯合物(以下，亦稱為ALq3)所形成之發光層作為設置於電極間之薄膜的元件之開發，相較於以往使用蒽等單結晶之元件時，則顯示出大幅之發光效率的改善效果，使得具有自我發光．高速應答性之特徵的高性能平面面板實用化指日可待。
對於提高元件發光效率之試驗，目前已有不使用螢光發光材料而使用磷光發光材料之研究。由上述設有芳香族二胺所形成之電洞輸送層與ALq3所形成之發光層之元件開始，已有許多元件為利用螢光發光者，但是利用三重態激動狀態所產生之磷光發光，與以往之使用螢光(一重態)的元件相比較時，可提高3~4倍左右之效率。為達此目的，已有使用薰草素衍生物或二苯甲酮衍生物作為發光層之研究，但僅得到極低亮度之結果。其後，對於利用三重態狀態之試驗，復有使用銪錯合物之研究，但其仍未產生高效率之發光。近年來，以專利文獻1所列舉之發光的高效率化或長壽命化為目的之銥錯合物等之有機金屬錯合物為中心進行多種研究。
〔專利文獻1〕特表2003-515897號公報
〔專利文獻2〕特開2001-313178號公報
〔專利文獻3〕特開2002-352957號公報
〔專利文獻4〕特開平11-162650號公報
〔專利文獻5〕特開平11-176578號公報
〔專利文獻6〕WO2007/063796號公報
為得到更高發光效率，與摻雜物材料同樣地，所使用之主體材料亦極為重要。被提案作為主體材料之代表性化合物，例如專利文獻2所介紹之咔唑化合物之4,4'-雙(9-咔唑基)聯苯(以下，亦稱為CBP)等。綠色磷光發光材料之三(2-苯基吡啶)銥錯合物(以下，亦稱為Ir(ppy)3
)之主體材料於使用CBP時，CBP相對於電洞輸送能而言，其電子輸送能更為劣化，發光層中之電荷之平衡發生崩壞，過剰之電洞由陰極側流出，發光層中之再鍵結準確率降低將會招致發光效率降低。此外，此時，發光層之再鍵結區域僅限於陰極側枝界面附近的狹窄區域，故相對於Ir(ppy)3
之最低激動三重項狀態之使用能量階層較低之如Alq3等電子輸送材料時，將因摻雜物向電子輸送材料之三重項激動能量之移動而引起發光效率降低之情形。
又，專利文獻3也有揭示3-苯基-4-(1'-萘基)-5-苯基-1,2,4-三唑(以下，亦稱為TAZ)可作為磷光有機EL元件之主體材料之提案，但TAZ相對於電子輸送能，其電洞輸送能較差，故發光區域變成電洞輸送層側。此時，電洞輸送材料將會影響Ir(ppy)3
所產生發光效率。例如，電洞輸送層就高性能、高信賴性、長使用壽命等觀點而言，使用最佳之4,4'-雙(N-(1-萘基)-N-苯基胺基)聯苯(以下，亦稱為NPB)之情形，因最低激動三重項狀態之能量階層之關係，可使三重項激動能量由Ir(ppy)3
向NPB移動，而會造成發光效率降低等問題。
此外，因CBP或TAZ等化合物容易結晶化．凝集，而造成薄膜形狀劣化以外，Tg則因結晶性高而無法進行觀測。如此，發光層內之薄膜形狀無法安定，將會造成元件之驅動壽命降低，耐熱性亦降低之不良影響。
由前述例示得知，為使有機EL元件具有高發光效率時，則須尋求一種同時具有高電洞輸送能與高電子輸送能，且兩電荷(電洞．電子)輸送能具有優良平衡性之主體材料。此外，亦尋求一種同時具有優良之安定電化學性，高耐熱性之非晶質安定性之化合物。
又，專利文獻4、5及6等揭示一種吲哚咔唑化合物使用於有機EL元件之內容，但仍期待一種具有更優良性能之有機EL元件用化合物。
有機EL元件應用於平面面板．顯示器等顯示元件時，必須同時充分確保元件發光效率之改善與驅動時之安定性。本發明即為鑑於上述之現狀，而以提出一種具有高效率與高驅動安定性之實際上有用之有機EL元件及適用其之化合物為目的。
本發明者們，經過深入研究結果，發現使用具有特定構造之化合物作為有機EL元件使用時，即可解決上述問題，因而完成本發明。
即，本發明為提供一種使用特定之吲哚咔唑骨架之化合物之有機EL元件及其所適用之有機EL元件用化合物。
本發明之有機電致發光元件用化合物，係如下述通式(1)所表示。
其中，環a為與2個之鄰接環縮合之式(a1)或(a2)所表示之芳香環或雜環，環a'為與3個之鄰接環縮合之式(a1)所表示之芳香環或雜環。環b為與2個之鄰接環縮合之式(b1)所表示之雜環。X表示CR或N。L為具有縮環構造之n+1價之芳香族雜環基。Ar1
~Ar3
為獨立之烷基、芳烷基、取代或未取代之芳香族烴基或芳香族雜環基，但Ar2
、Ar3
不為含氮六員環。R及R1
~R7
為獨立之氫、烷基、芳烷基、烯基、炔基、氰基、二烷基胺基、二芳基胺基、二芳烷基胺基、胺基、硝基、醯基、烷氧羰基、羧基、烷氧基、烷基磺醯基、鹵烷基、羥基、醯胺基、取代或未取代之芳香族烴基或芳香族雜環基，其中之二個相鄰接之情形，可相互鍵結形成環。n為0~5之整數。
通式(1)所表示之有機電致發光元件用化合物，為下述通式(2)或(3)所表示之化合物。
其中，環b、L、Ar1
、R1
~R4
、n為與通式(1)之環b、L、Ar1
、R1
~R4
、n具有相同之意義。
其中，L、Ar1
、Ar3
、R1
~R4
、n為與通式(1)之L、Ar1
、Ar3
、R1
~R4
、n具有相同之意義。
又，本發明為有關具有含有上述有機電致發光元件用化合物之有機層的有機電致發光元件之發明。其優點為，該有機層為由發光層、電洞輸送層、電洞注入層、電子輸送層、電子注入層及電洞阻止元件層所選擇之至少一個之層。更佳者為，該有機層為發光層，且該發光層為以含有磷光發光性摻雜物與上述之有機電致發光元件用化合物作為主體材料之方式的有機電致發光元件。
本發明之有機EL元件用化合物，係以上述通式(1)所表示。通式(1)所表示之化合物，典型而言，其為具有咔唑環與吲哚環縮合所得之吲哚咔唑骨架。咔唑環之N，為與具有縮環構造之芳香族雜環基L鍵結。
通式(1)中，環a為與2個之鄰接環縮合之式(a1)或(a2)所表示之芳香環或雜環。環a為式(a2)所表示之雜環之情形中，環a'為與3個之鄰接環縮合之式(a1)所表示之芳香環或雜環。式(a1)中，X表示CR或N。其中之R為表示與R1
~R7
為同樣之基，較佳為氫原子。環b為與2個之鄰接環縮合之式(b1)所表示之雜環。
通式(1)中，L為具有縮環構造之n+1價之芳香族雜環基。其中，n為0~5，較佳為0~2之數。
具有縮環構造之芳香族雜環基之較佳具體例，例如下述所示芳香族雜環化合物去除n+1個氫原子所得之基等。
上述芳香族雜環化合物之具體例如，苯并噻吩、苯并噻唑、噻蒽、異苯并呋喃、苯并噁唑、克烷烯(chromene)、二苯并哌喃、苯氧基二苯并哌喃、吲哚嗪、異吲哚、吲哚、苯并咪唑、吲唑、苯并三唑、嘌呤、喹巾(Quinolizin)、異喹啉、喹啉、呔、喹啉、喹唑啉、啉(cinnoline)、喋啶、咔唑、咔啉、啡啶、吖啶、呸啶、啡啉、啡、啡噻、啡、二苯并戴奧辛等。
通式(1)、(2)及(3)中，Ar1
~Ar3
為獨立之烷基、芳烷基、取代或未取代之芳香族烴基或芳香族雜環基。其中，Ar2
、Ar3
為芳香族雜環基之情形，其不為含氮六員環。
通式(1)、(2)及(3)中，Ar1
~Ar3
為烷基之情形，其碳數以1~6為佳，為芳烷基之情形，其碳數以7~13為佳，為取代或未取代之芳香族烴基或芳香族雜環基之情形，其碳數以3~15為佳。
未取代之芳香族烴基之較佳具體例如，由苯、萘、蒽、菲、茚、聯苯、三苯基、四苯基去除1個氫原子所得之1價基等，更佳為由苯、聯苯、三苯基去除1個氫原子所得之1價基等。
未取代之芳香族雜環基之較佳具體例如，由噻吩、噻唑、呋喃、噁唑、吡喃、吡咯、咪唑、吡唑、異噻唑、異噁唑、呋咱(furazan)、三唑、吡啶、吡、嘧啶、嗒、三、苯并噻吩、苯并噻唑、噻嗯、異苯并呋喃、苯并噁唑、克烷烯(chromene)、二苯并哌喃、苯氧基二苯并哌喃、吲哚嗪、異吲哚、吲哚、苯并咪唑、吲唑、苯并三唑、嘌呤、喹巾(Quinolizin)、異喹啉、喹啉、呔、啶、喹啉、喹唑啉、啉(cinnoline)、喋啶、咔唑、咔啉、啡啶、吖啶、呸啶、啡啉、啡、啡噻、啡 、二苯并戴奧辛去除1個氫原子所得之1價基等，更佳為由吡啶、吡、嘧啶、嗒、三去除1個氫原子所得之1價基等。
R1
~R7
為獨立之氫、烷基、芳烷基、烯基、炔基、氰基、二烷基胺基、二芳基胺基、二芳烷基胺基、胺基、硝基、醯基、烷氧羰基、羧基、烷氧基、烷基磺醯基、鹵烷基、羥基、醯胺基、取代或未取代之芳香族烴基或芳香族雜環基。其中之二個相鄰接之情形，可相互鍵結形成縮環。較佳為氫或烷基。
R1
~R7
為烷基之情形，其碳數以1~6為佳，為烯基、炔基之情形，其碳數以2~6為佳，為芳烷基之情形，其碳數以7~13為佳，為取代或未取代之芳香族烴基或芳香族雜環基之情形，其碳數以3~15為佳。又，為二烷基胺基之情形，其碳數以2~10為佳，為二芳基胺基、二芳烷基胺基烷基之情形，其碳數以6~20為佳，為醯基、烷氧羰基之情形，其碳數以2~10為佳，為烷氧基、烷基磺醯基、鹵烷基之情形，其碳數以1~6為佳。
R1
~R7
之中之二個為鄰接之情形，其可相互鍵結形成縮環。例如，二個乙烯基相鄰接之情形，其可互相鍵結，乙烯基分別與鍵結之吲哚咔唑骨架中之二個碳共同形成六員環之含氮縮合六環。又，二個之鄰接取代基為二組之情形，其可形成含氮縮合七環。
上述Ar1
~Ar3
及R1
~R7
中，該些為具有取代基之芳香族烴基或芳香族雜環基之情形，較佳之取代基為碳數1~6之烷基、碳數1~6之烷氧基、碳數6~12之芳基氧基、烷硫基、取代胺基、乙醯基、苯基、聯苯基、聯三苯基、萘基、吡啶基、嘧啶基、三基、咪唑啉基、噻嗯基、咔唑基等。
通式(2)及(3)為表示通式(1)之較佳例式，通式(2)為通式(1)之環a限制為苯環之構造，通式(3)為限定環b之鍵結形式之構造。
本發明之有機EL元件用化合物可以公知之方法容易製造。例如，通式(1)所表示之化合物，可參考使用Synlett,2005,No.1,p42-48所示合成例依以下之反應式予以製造。
通式(1)或通式(2)、(3)所表示之化合物之較佳具體例係如以下所示，但並非限定於該內容。
本發明之有機電致發光元件用化合物，於包含於有機EL元件之有機層時，可提供優良之有機電致發光元件。較佳者為，以包含於由發光層、電洞輸送層、電子輸送層及電洞阻礙元件層所選出之至少一個之有機層者為佳。更佳者為，以包含於含有磷光發光摻雜物之發光層的主體材料為佳。
發光層中之磷光發光摻雜物材料，以包含於由釕、銠、鈀、銀、錸、鋨、銥、鉑及金所選出之至少一個之金屬的有機金屬錯合物者為佳。該有機金屬錯合物，係記載於前述專利文獻等而屬公知技術，故可由其中選擇使用。
較佳之磷光發光摻雜物，例如具有以Ir等貴金屬元素作為中心金屬之Ir(ppy)3
等之錯合物類、Ir(bt)2．acac3等之錯合物類、PtOEt3等之錯合物類。該些錯合物類之具體例係如以下所示，但並不僅限定於下述之化合物。
發光層中所含有之前述磷光發光摻雜物之量為2~20重量%，較佳為5~10重量%之範圍為佳。此時，主體材料可使用本發明之有機EL元件用化合物，其於發光層中所含有之量為50重量%以上，較佳為80~95重量%之範圍為佳。
其次，將對本發明之有機EL元件之構造於參照圖示下進行說明，但本發明之有機EL元件之構造並不受任何圖示所限定。
圖1為本發明所使用之一般性有機EL元件構造例之典型截面圖，1為基板、2為陽極、3為電洞注入層、4為電洞輸送層、5為發光層、6為電子輸送層、7為陰極。本發明之有機EL元件，以具有基板、陽極、發光層及陰極為必要之層，除必要之層以外之層，可具有電洞注入輸送層、電子注入輸送層等亦可，此外，於發光層與電子注入輸送層之間可再具有電洞阻礙層亦可。又，電洞注入輸送層係指電洞注入層與電洞輸送層中任一者或二者之意，電子注入輸送層係指電子注入層或電子輸送層中任一者或二者之意。
基板1為作為有機EL元件之支撐體之物，其可使用石英或玻璃板、金屬板或金屬箔、塑膠薄膜或薄片等。特別是以玻璃板為佳。
陽極2，具有對電洞注入層3進行電洞注入之機能。陽極2，通常可使用鋁、金、銀、鎳、鈀、鉑等之金屬，銦及/或錫之氧化物(ITO)等之金屬氧化物、碘化銅等之鹵化金屬、石墨，或聚(3-甲基噻吩)、聚吡咯、聚苯胺等之導電性高分子等所構成。
發光層5為，於提供電場之電極間，可使由陽極2所注入之移動至電洞輸送層4之電洞，與，陰極7所注入之移動至電子輸送層6之電子經由再鍵結產生激動而顯示發光之發光物質所形成。發光層5，以含有由發光物質之摻雜物材料與前述有機EL元件用化合物所形成之主體材料者為佳。
陰極7，具有介由電子輸送層6將電子注入發光層5之機能。陰極7所使用之材料，就可有效地進行電子注入等目的，以功係數較低之金屬為佳，例如可使用錫、鎂、銦、鈣、銫、鋁、銀等之適當之金屬，或該些之合金。具體例如鎂-銀合金、鎂-銦合金、鋁-鋰合金等。
電洞注入層3、電洞輸送層4、電子輸送層6可為任意之有機層，電洞注入層3為使電洞可有效率地經由陽極2注入電洞輸送層4之目的而被使用者，電洞輸送層4及電子輸送層6，分別具有使電洞、電子移動至發光層5之機能。又，電子注入層可設置於陰極7與電子輸送層6之間。該些層所使用之材料係為公知之材料。
電洞注入材料，例如銅酞菁(CuPC)等之酞菁化合物、聚苯胺、聚噻吩等之有機化合物，或釩氧化物、釕氧化物、鉬氧化物等金屬氧化物等。
電洞輸送材料例如三唑衍生物、氧雜二唑衍生物、咪唑衍生物、聚芳基烷衍生物、吡唑啉衍生物及吡唑啉酮衍生物、伸苯二胺衍生物、NPB等之芳基胺衍生物、胺基取代查酮衍生物、噁唑衍生物、苯乙烯基蒽衍生物、芴酮衍生物、腙衍生物、二苯乙烯衍生物、矽胺烷衍生物、苯胺系共聚物，又，例如導電性高分子低聚物，特別是噻吩低聚物等。
電子輸送材料例如Alq3等之金屬錯合物、10-羥基苯并〔h〕喹啉之金屬錯合物、氧雜二唑衍生物、二苯乙烯基聯苯衍生物、矽咯衍生物、3-或5-羥基黃酮金屬錯合物、苯并噁唑金屬錯合物、苯并噻唑金屬錯合物、三苯并咪唑啉基苯喹唑啉化合物、啡啉衍生物、2-t-丁基-9,10-N,N'-二胺基蒽酮二亞胺、n型氫化非晶質碳化矽、n型硫化鋅、n型硒化鋅等。
又，亦可形成與圖1相反之構造，即，於基板1上依序形成陰極7、電子輸送層6、發光層5、電洞輸送層4、陽極2之層亦為可能，如前所述般，其於至少一者為具有高度透明性之2片基板之間設置本發明之有機EL元件亦為可能。此情形中，亦可配合必要性而追加層結構，或省略皆可。
本發明之有機EL元件，可為單一之元件，而以陣列狀配置之構造所形成之元件，或於陽極與陰極形成X-Y矩陣狀配置之構造之任一者皆可使用。本發明之有機EL元件，其於發光層中經由含有具有特定骨架之化合物，與磷光發光摻雜物結果，可得到相較於以往使用一重態狀態產生發光之元件為具有更高發光效率，且可大幅改善驅動安定性之元件，而應用於全彩色彩或高彩色彩之面板時，可發揮出優良之性能。
以下，本發明將配合實施例作更詳細之說明，本發明當然不受該些實施例所限定，且於未超過本發明實質內容之範圍，可以各種實施形成實施。又，化合物係對應於上述化學式所附屬之編號。
於經氮氣取代之2000ml三口燒瓶中，加入1,2-環己烷二酮33.3g(297.0mmol)、苯基肼鹽酸鹽86.0g(594.7mmol)於其中加入乙醇1000ml後進行攪拌。其後，於同燒瓶內以5分鐘時間滴入濃硫酸3.0g(30.6mmol)後，加熱至65℃，攪拌4小時。冷卻至室溫後，濾取所生成之紫茶色結晶，將所得之結晶以乙醇500ml洗淨二次、淤漿化洗淨(reslurry washing)。其經由減壓乾燥結果，得紫茶色粉末80.0g(280.5mmol，產率96.3%)。
其次，將上述紫茶色粉末72.0g(261.5mmol)加入1000ml三口燒瓶中，於其中再加入乙酸720g、三氟乙酸72.0g後攪拌。隨後，加熱至100℃，再攪拌15小時。冷卻至室溫後，濾取所生成之黃色結晶，所得之結晶以乙酸200ml淋洗洗淨後，再以己烷200ml淋洗洗淨。將其減壓乾燥後，得白色粉末A’ 30.0g(117.1mmol、產率44.8%)。所得之白色粉末A’為吲哚〔2,3-a〕咔唑。
其次，於氮氣取代之1000ml三口燒瓶中，加入上述所得之白色粉末26.0g(101.4mmol)、碘化苯122.7g(601.4mmol)、溴化銅54.7g(287.2mmol)、碳酸鉀66.7g(482.6mmol)、喹啉800ml後攪拌。隨後加熱至190℃，攪拌72小時。先冷卻至室溫後，加入水500ml、二氯甲烷500ml，進行攪拌後，濾取所生成之黃色結晶。將濾液移至2000ml分液漏斗中，區分為有機層與水層。有機層以500ml之水洗淨三次，其後，將所得之有機層以硫酸鎂脫水，先將硫酸鎂濾除後，將溶媒減壓餾除。其後，以管柱滲透色層分析法精製，得白色固體A 13.7g(41.2mmol、產率40.6%)。所得白色固體A為11-苯基吲哚〔2,3-a〕咔唑。
於排氣氮取代之100ml三口燒瓶中，加入乙酸鈀(II)0.52g(2.33mmol)、三-tert-丁基膦1.97g(9.74mmol)、脫水二甲苯45ml後進行攪拌。隨後加熱至80℃，攪拌30分鐘，進行觸媒之製作。其次，於排氣氮取代之1000ml三口燒瓶中，加入11-苯基吲哚〔2,3-a〕咔唑15.4g(46.3mmol)、3-溴化喹啉14.5g(69.7mmol)、鈉-tert-丁氧化物18.8g(195mmol)、脫水二甲苯430ml後攪拌。加熱至80℃後，再加入上述所製得之觸媒溶液。隨後加熱至130℃，攪拌17小時。冷卻至室溫後，加入水340ml，進行攪拌後，濾取所生成之黃色結晶。濾取之結晶使用甲醇200ml洗淨2次，淤漿化洗淨。以管柱色層分析法精製後，以甲苯加熱進行淤漿化，得黃色結晶12.0g(26.1mmol、產率56.4%)。該黃色結晶為化合物3。
APCI-MS，m/z 460〔M+H〕+
圖1中，製作追加有電子注入層之構成的有機EL元件。於形成有膜厚150nm之由ITO所形成之陽極的玻璃基板上，將各薄膜以真空蒸鍍法，以真空度4.0×10-4
Pa進行層合。首先，於ITO形成作為電洞注入層之20mm厚度之銅酞菁(CuPC)。其次，形成作為電洞輸送層之40nm之NPB。其次，於電洞輸送層上，將作為發光層之主體材料的化合物3，與作為摻雜物之Ir(ppy)3
由不同之蒸鍍源進行共蒸鍍，而形成厚度35nm之發光層。此時，Ir(ppy)3
之濃度為7.0 wt%。其次，形成作為電子輸送層之厚度40nm之Alq3。隨後，再於電子輸送層上，形成作為電子注入層之厚度0.5nm之氟化鋰(LiF)。最後，再於電子注入層上，形成作為電極之厚度170nm之鋁(Al)，而製得有機EL元件。
將所得之有機EL元件連接外部電源，施加直流電壓結果，確認其具有表1所示之發光特性。表1中，顯示亮度、電壓及發光效率等係以10mA/cm2
之數值表示。又，元件發光圖譜之最大波長為517 nm，得知其為得到Ir(ppy)3
所產生之發光。
發光層之主體材料，除使用化合物2以外，其他皆依實施例2相同方法製作有機EL元件。
發光層之主體材料，除使用化合物9以外，其他皆依實施例2相同方法製作有機EL元件。
發光層之主體材料，除使用化合物18以外，其他皆依實施例2相同方法製作有機EL元件。
發光層之主體材料，除使用化合物20以外，其他皆依實施例2相同方法製作有機EL元件。
發光層之主體材料，除使用化合物23以外，其他皆依實施例2相同方法製作有機EL元件。
發光層之主體材料，除使用化合物26以外，其他皆依實施例2相同方法製作有機EL元件。
發光層之主體材料，除使用化合物29以外，其他皆依實施例2相同方法製作有機EL元件。
發光層之主體材料，除使用化合物31以外，其他皆依實施例2相同方法製作有機EL元件。
發光層之主體材料，除使用化合物33以外，其他皆依實施例2相同方法製作有機EL元件。
發光層之主體材料，除使用化合物35以外，其他皆依實施例2相同方法製作有機EL元件。
除電洞輸送層使用HMTPD，發光層之主體材料使用TAZ以外，其他皆依實施例2相同方法製作有機EL元件。
發光層之主體材料，除使用TAZ以外，其他皆依實施例2相同方法製作有機EL元件。
對發光特性進行評估結果整理如表1所示。表1中，亮度、電壓及發光效率係以10mA/cm2
之數值表示。又，實施例2~12及比較例1~2中所得之有機EL元件，無論任一個，其元件發光圖譜之最大波長為517 nm，確認其得到由Ir(ppy)3
產生之發光。
本發明之有機EL元件，可於低電壓下進行高亮度．高效率之發光。因此，本發明之有機EL元件可應用於以平面面板．顯示器(例如OA電腦用或壁掛式電視)、車用顯示元件、手提電話顯示器或平面發光體為特徵所產生之光源(例如，影印機之光源、液晶顯示器或計測器類之背光光源)、顯示板、標識燈號等，其為具有極大技術性價值者。
1．．．基板
2．．．陽極
3．．．電洞注入層
4．．．電洞輸送層
5．．．發光層
6．．．電子輸送層
7．．．陰極
圖1為有機EL元件之一例示的截面圖。
1．．．基板
2．．．陽極
3．．．電洞注入層
4．．．電洞輸送層
5．．．發光層
6．．．電子輸送層
7．．．陰極
Claims (6)
- 一種有機電致發光元件用化合物，其特徵為下述通式(1)所示者，
- 如申請專利範圍第1項之有機電致發光元件用化合物，其係如下述通式(2)所示者，
- 如申請專利範圍第1項之有機電致發光元件用化合物，其係如下述通式(3)所示者，
- 一種有機電致發光元件，其特徵為，具有含有申請專利範圍第1~3項中任一項之有機電致發光元件用化合物之有機層。
- 如申請專利範圍第4項之有機電致發光元件，其中，含有有機電致發光元件用化合物之有機層為由發光層、電洞輸送層、電洞注入層、電子輸送層、電子注入層及電洞阻礙元件層所選出之至少一個之層。
- 如申請專利範圍第4項之有機電致發光元件，其中，含有有機電致發光元件用化合物之有機層為發光層，該發光層為含有磷光發光性摻雜物與該有機電致發光元件用化合物作為主體材料。
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| EP2284920A1 (en) | 2011-02-16 |
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| EP2284920A4 (en) | 2012-08-22 |
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