TWI636972B - 用於有機電致發光元件之化合物及包含該化合物之有機電致發光元件 - Google Patents
用於有機電致發光元件之化合物及包含該化合物之有機電致發光元件 Download PDFInfo
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- TWI636972B TWI636972B TW103128322A TW103128322A TWI636972B TW I636972 B TWI636972 B TW I636972B TW 103128322 A TW103128322 A TW 103128322A TW 103128322 A TW103128322 A TW 103128322A TW I636972 B TWI636972 B TW I636972B
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- heterocycloalkyl
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 58
- 238000005401 electroluminescence Methods 0.000 claims abstract description 67
- 239000010410 layer Substances 0.000 claims description 75
- 125000000217 alkyl group Chemical group 0.000 claims description 53
- 125000003118 aryl group Chemical group 0.000 claims description 51
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 44
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 43
- 125000001072 heteroaryl group Chemical group 0.000 claims description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 40
- 239000012044 organic layer Substances 0.000 claims description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
- 238000002347 injection Methods 0.000 claims description 13
- 239000007924 injection Substances 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 230000000903 blocking effect Effects 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 239000002019 doping agent Substances 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 38
- 238000012546 transfer Methods 0.000 abstract description 17
- 239000000243 solution Substances 0.000 description 30
- -1 amine compound Chemical class 0.000 description 19
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- 239000013067 intermediate product Substances 0.000 description 15
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- 238000004440 column chromatography Methods 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
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- 125000000524 functional group Chemical group 0.000 description 8
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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 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
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- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 5
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- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 5
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 5
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 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
- 229910052760 oxygen Inorganic materials 0.000 description 4
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 125000001424 substituent group Chemical group 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
- 0 CC(C)C=C(CCCI*(CC(C*)F)=*)c1c(C)c(C(*C=C(*2)[*@](CC=C*=CC*)*=**(*I)C=*)C=C2I[*+])cc(C(CC(*)C*C#*)C2C**)*1*2=C Chemical compound CC(C)C=C(CCCI*(CC(C*)F)=*)c1c(C)c(C(*C=C(*2)[*@](CC=C*=CC*)*=**(*I)C=*)C=C2I[*+])cc(C(CC(*)C*C#*)C2C**)*1*2=C 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
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- 230000000052 comparative effect Effects 0.000 description 3
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- 125000001041 indolyl group Chemical group 0.000 description 3
- 238000004811 liquid chromatography Methods 0.000 description 3
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- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 238000001771 vacuum deposition Methods 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
- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 2
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical group CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 2
- QYNTUCBQEHUHCS-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n-[4-[4-(n-[4-(n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-1-n,4-n-diphenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 QYNTUCBQEHUHCS-UHFFFAOYSA-N 0.000 description 2
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 2
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 2
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- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- TWWQCBRELPOMER-UHFFFAOYSA-N [4-(n-phenylanilino)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 TWWQCBRELPOMER-UHFFFAOYSA-N 0.000 description 2
- FZYXURZMAQWVFY-UHFFFAOYSA-K [Ir+3].[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1.FC1=C(C#N)C(F)=CC(C=2N=CC=CC=2)=C1.FC1=C(C#N)C(F)=CC(C=2N=CC=CC=2)=C1 Chemical compound [Ir+3].[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1.FC1=C(C#N)C(F)=CC(C=2N=CC=CC=2)=C1.FC1=C(C#N)C(F)=CC(C=2N=CC=CC=2)=C1 FZYXURZMAQWVFY-UHFFFAOYSA-K 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
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- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 238000005229 chemical vapour deposition Methods 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
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- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- KFGVRWGDTLZAAO-UHFFFAOYSA-N cyclopenta-1,3-diene dicyclohexyl(cyclopenta-1,3-dien-1-yl)phosphane iron(2+) Chemical compound [Fe++].c1cc[cH-]c1.C1CCC(CC1)P(C1CCCCC1)c1ccc[cH-]1 KFGVRWGDTLZAAO-UHFFFAOYSA-N 0.000 description 2
- 229910052805 deuterium Inorganic materials 0.000 description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- JZRYQZJSTWVBBD-UHFFFAOYSA-N pentaporphyrin i Chemical compound N1C(C=C2NC(=CC3=NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 JZRYQZJSTWVBBD-UHFFFAOYSA-N 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
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 2
- 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 2
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- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- WTGQALLALWYDJH-WYHSTMEOSA-N scopolamine hydrobromide Chemical compound Br.C1([C@@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 WTGQALLALWYDJH-WYHSTMEOSA-N 0.000 description 2
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- 238000003756 stirring Methods 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 125000004950 trifluoroalkyl group Chemical group 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 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
- TXBFHHYSJNVGBX-UHFFFAOYSA-N (4-diphenylphosphorylphenyl)-triphenylsilane Chemical compound C=1C=CC=CC=1P(C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(=O)C1=CC=CC=C1 TXBFHHYSJNVGBX-UHFFFAOYSA-N 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
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- LBRQOQKUHZVOOK-UHFFFAOYSA-N 1,3,5-tribromobenzene Chemical compound BrC1=CC(=CC(=C1)Br)Br.BrC1=CC(=CC(=C1)Br)Br LBRQOQKUHZVOOK-UHFFFAOYSA-N 0.000 description 1
- KARUMYWDGQTPFL-UHFFFAOYSA-N 1,3-dibromo-5-iodobenzene Chemical compound BrC1=CC(Br)=CC(I)=C1 KARUMYWDGQTPFL-UHFFFAOYSA-N 0.000 description 1
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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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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Abstract
本發明關於一種用於有機電致發光元件的化合物及一種包含該化合物的有機電致發光元件。此用於有機電致發光元件的化合物具有高的熱穩定性、高的三重態能量及高電洞傳遞能力,且包含該化合物的有機電致發光元件在熱穩定性及發光效率方面獲得提升。當此化合物用來作為電洞傳遞材料時,磷光發光材料的三重態激子受到約束,從而提升該有機電致發光元件的效率。
Description
本發明有關用於有機電致發光元件的化合物及包含該化合物的有機電致發光元件,且更明確言之,是有關一種用於有機電致發光元件的雜環結構胺系化合物,及關於一種包含該胺系化合物的有機電致發光元件。
相較於諸如液晶顯示器(LCD)、電漿顯示面板(PDP)、場發射顯示器(FED)等其他平面顯示器而言,有機電致發光(EL)元件具有較簡單的結構、諸多處理優點、較高亮度、卓越的視角性質、更快的反應速度及較低的驅動電壓,並因此獲得全面發展而得以作為平板顯示器顯示器(例如壁掛式電視,等等)的光源或上述顯示器、照明器、廣告看板及諸如此類者的背光單元。
通常,當對有機EL元件施加直流電壓時,從陽極(anode)射出的電洞與陰極(cathode)射出的電子會再結合而形
成電子-電洞對,也就是激子。當激子回到穩定的基態時,會將相應的能量傳遞給發光材料並進而轉換成光。
自從伊士曼柯達公司的C.W.Tang等人藉由在相反電極之間形成串聯有機薄膜而製成有機EL元件後(參閱C.W.Tang、S.A.Vanslyke,Applied Physics Letters期刊第51卷第913頁1987年),為了提高有機EL元件的效率及穩定性,持續對有機材料進行廣泛且深入的研究,以尋求可用於具有多層薄膜結構之有機EL元件的有機材料。此種串聯式有機EL元件的效率及壽命與薄膜材料的分子結構有著密切關聯性。例如,量子效率可能取決於薄膜材料的結構,尤其是主體材料(host material)、電洞傳遞層材料或電子傳遞層材料的結構而有極大變化。當材料的熱穩定性降低時,該材料可能在高溫或驅動溫度下進行結晶,而導致發生元件使用壽命縮短這類不樂見的情況。
由於目前已知可用於有機EL元件之電洞傳遞材料藉由真空沈積法所形成的薄膜具有熱不穩定性且電性亦不穩定,故驅動元件時所生成的熱可能導致材料快速結晶且薄膜材料可能變化,從而導致發生元件發光效率降低這類令人不悅的情形,因此該等材料都有些問題。再者,不發光部分(稱為暗點)發生機率可能增加,並當以固定電流驅動時,電壓可能提高而不幸導致元件受損。
又由於磷光發光材料具有低的三重態能量,故使用磷光發光材料的有機EL元件無法約束發光層之發光材料中所產生的三重態激子,從而導致元件發光效率降低這種令人
不快的情況。
因此,本發明的目的是提供一種用於有機EL元件的化合物,該化合物可具有高的熱穩定性、高的三重態能量及高電洞傳遞能力。
本發明的另一目的是提供一種有機EL元件,該有機EL元件包含上述化合物並因而增進熱穩定性及發光效率,且在該有機EL元件中,上述化合物是用來作為電洞傳遞層,從而約束磷光發光材料的三重態激子,最終增進該有機EL元件的效率。
為達成上述目的,本發明之一態樣提供一種用於有機EL元件的化合物,該化合物如以下化學式1所示者。
在化學式1中,Ar1為經取代或未經取代的C1至C30烷基、經取代或未經取代的C3至C30環烷基、經取代或未經取代的C2至C30雜環烷基、經取代或未經取代的C6至C30芳基或經取代或未經取代的C1至C30雜芳基,或Ar1進一步
與該Ar1所連接之碳原子旁邊的碳原子耦合以形成經取代或未經取代的C3至C30稠合環烷基、經取代或未經取代的C2至C30稠合雜環烷基、經取代或未經取代的C6至C30稠合芳基或經取代或未經取代的C1至C30稠合雜芳基;R1為氫原子、經取代或未經取代的C1至C30烷基、經取代或未經取代的C3至C30環烷基、經取代或未經取代的C2至C30雜環烷基、經取代或未經取代的C6至C30芳基或是經取代或未經取代的C1至C30雜芳基,或R1與Ar1耦合以形成經取代或未經取代的C1至C30稠合環烷基、經取代或未經取代的C2至C30稠合雜環烷基、經取代或未經取代的C6至C30稠合芳基或是經取代或未經取代的C1至C30稠合雜芳基;及R2至R13為彼此相同或互不相同,且R2至R13各自獨立地為氫原子、經取代或未經取代的C1至C30烷基、經取代或未經取代的C3至C30環烷基、經取代或未經取代的C2至C30雜環烷基、經取代或未經取代的C6至C30芳基或是經取代或未經取代的C1至C30雜芳基,或R2至R13其中至少一者進一步與其所連接之碳原子旁邊的碳原子耦合以形成經取代或未經取代的C3至C30稠合環烷基、經取代或未經取代的C2至C30稠合雜環烷基、經取代或未經取代的C6至C30稠合芳基或是經取代或未經取代的C1至C30稠合雜芳基。
根據本發明的較佳實施例,該用於有機EL元件的化合物如以下化學式2所示。
[化學式2]
在化學式2中,R2至R16為彼此相同或互不相同,且R2至R16各自獨立地為氫原子、經取代或未經取代的C1至C30烷基、經取代或未經取代的C3至C30環烷基、經取代或未經取代的C2至C30雜環烷基、經取代或未經取代的C6至C30芳基或經取代或未經取代的C1至C30雜芳基,或R2至R16其中至少一者進一步與其所連接之碳原子旁邊的碳原子耦合以形成經取代或未經取代的C3至C30稠合環烷基、經取代或未經取代的C2至C30稠合雜環烷基、經取代或未經取代的C6至C30稠合芳基或是經取代或未經取代的C1至C30稠合雜芳基;及R1及R17為彼此相同或互不相同,且R1及R17各自獨立地為氫原子、經取代或未經取代的C1至C30烷基、經取代或未經取代的C3至C30環烷基、經取代或未經取代的C2至C30雜環烷基、經取代或未經取代的C6至C30芳基或經取代或未經取代的C1至C30雜芳基,或R1及R17分別連接而與R1及R17兩者之間的4個碳原子共同形成經取代或未經取代的C1至C30稠合環烷基、經取代或未經取代的C2至C30
稠合雜環烷基、經取代或未經取代的C6至C30稠合芳基或經取代或未經取代的C1至C30稠合雜芳基。
根據本發明較佳實施例,該用於有機EL元件的化合物如選自以下化學式3至化學式6中之任一化學式所示:
在化學式3至化學式6中,X1至X3為彼此相同或互不相同,且X1至X3各自獨立地為氧原子、硫原子、或
Ar2是經取代或未經取代的C1至C30烷基、經取代或未經取代的C3至C30環烷基、經取代或未經取代的C2至
C30雜環烷基、經取代或未經取代的C6至C30芳基或經取代或未經取代的C1至C30雜芳基;R22及R23彼此相同或互不相同,且R22及R23各自獨立地為氫原子、經取代或未經取代的C1至C30烷基、經取代或未經取代的C3至C30環烷基、經取代或未經取代的C2至C30雜環烷基、經取代或未經取代的C6至C30芳基或經取代或未經取代的C1至C30雜芳基;R2至R13為彼此相同或互不相同,且R2至R13各自獨立地為氫原子、經取代或未經取代的C1至C30烷基、經取代或未經取代的C3至C30環烷基、經取代或未經取代的C2至C30雜環烷基、經取代或未經取代的C6至C30芳基或經取代或未經取代的C1至C30雜芳基,或R2至R13其中至少一者進一步與其所連接之碳原子旁邊的碳原子耦合以形成經取代或未經取代的C3至C30稠合環烷基、經取代或未經取代的C2至C30稠合雜環烷基、經取代或未經取代的C6至C30稠合芳基或經取代或未經取代的C1至C30稠合雜芳基;及R14至R16及R18至R21為彼此相同或互不相同,且R14至R16及R18至R21各自獨立地為氫原子、經取代或未經取代的C1至C30烷基、經取代或未經取代的C3至C30環烷基、經取代或未經取代的C2至C30雜環烷基、經取代或未經取代的C6至C30芳基或經取代或未經取代的C1至C30雜芳基。
根據本發明較佳實施例,X1為或Ar2是經取代或未經取代的C1至C30烷基、經取代
或未經取代的C3至C30環烷基、經取代或未經取代的C2至C30雜環烷基、經取代或未經取代的C6至C30芳基或經取代或未經取代的C1至C30雜芳基;及R22及R23彼此相同或互不相同,且R22及R23各自獨立地為氫原子、經取代或未經取代的C1至C30烷基、經取代或未經取代的C3至C30環烷基、經取代或未經取代的C2至C30雜環烷基、經取代或未經取代的C6至C30芳基或經取代或未經取代的C1至C30雜芳基。
根據本發明較佳實施例,X2及X3為彼此相同或互不相同,且X2及X3各自獨立地為氧原子或;及Ar2是經取代或未經取代的C1至C30烷基、經取代或未經取代的C3至C30環烷基、經取代或未經取代的C2至C30雜環烷基、經取代或未經取代的C6至C30芳基或經取代或未經取代的C1至C30雜芳基。
根據本發明較佳實施例,R14至R16為彼此相同或互不相同,且R14至R16各自獨立地為氫原子、 、經取代或未經取代的C1至C30烷基、經取代或未經取代的C3至C30環烷基或經取代或未經取代的C2至C30雜環烷基;X4為氧原子、硫原子、或Ar3是經取代或未經取代的C1至C30烷基、經取代或未經取代的C3至C30環烷基、經取代或未經取代的C2至
C30雜環烷基、經取代或未經取代的C6至C30芳基或經取代或未經取代的C1至C30雜芳基;R29及R30彼此相同或互不相同,且R29及R30各自獨立地為氫原子、經取代或未經取代的C1至C30烷基、經取代或未經取代的C3至C30環烷基、經取代或未經取代的C2至C30雜環烷基、經取代或未經取代的C6至C30芳基或經取代或未經取代的C1至C30雜芳基;及R24至R28彼此相同或互不相同,且R24至R28各自獨立地為氫原子、經取代或未經取代的C1至C30烷基、經取代或未經取代的C3至C30環烷基、經取代或未經取代的C2至C30雜環烷基、經取代或未經取代的C6至C30芳基或經取代或未經取代的C1至C30雜芳基。
根據本發明較佳實施例,R2至R13彼此相同或互不相同,且R2至R13各自獨立地為氫原子、經取代或未經取代的C1至C30烷基、經取代或未經取代的C3至C30環烷基、經取代或未經取代的C2至C30雜環烷基、經取代或未經取代的C6至C30芳基或經取代或未經取代的C1至C30雜芳基。
根據本發明較佳實施例,R2至R13彼此相同或互不
相同,且R2至R13各自獨立地為氫原子、、經取代或未經取代的C1至C30烷基、經取代或未經取代的C3至C30環烷基或經取代或未經取代的C2至C30雜環烷基;及R31及R32彼此相同或互不相同,且R31及R32各自獨立地為氫原子、經取代或未經取代的C1至C30烷基、經取
代或未經取代的C3至C30環烷基、經取代或未經取代的C2至C30雜環烷基、經取代或未經取代的C6至C30芳基或經取代或未經取代的C1至C30雜芳基。
該經取代或未經取代之C6至C30芳基的實例可包括經取代或未經取代的苯基、經取代或未經取代的聯苯基、經取代或未經取代的三聯苯基、經取代或未經取代的萘基(naphthalenyl)、經取代或未經取代的蒽基(anthracenyl)、經取代或未經取代的菲基(phenanthrenyl)、經取代或未經取代的茀基(fluorenyl)、經取代或未經取代的螺茀基(spirofluorenyl)、經取代或未經取代的芘基(pyrenyl)或經取代或未經取代的苝基(perylenyl)。
該經取代或未經取代之C1至C30雜芳基的實例可包括經取代或未經取代的吡啶基(pyridinyl)、經取代或未經取代的嘧啶基(pyrimidinyl)、經取代或未經取代的三基(triazinyl)、經取代或未經取代的噻吩基(thiophenyl)、經取代或未經取代的吡咯基(pyrrolyl)、經取代或未經取代的苯并噻吩基(benzothiophenyl)、經取代或未經取代的吲哚基(indolyl)、經取代或未經取代的咪唑并[1,2-a]吡啶基(imidazo[1,2-a]pyridinyl)、經取代或未經取代的苯并咪唑基(benzimidazolyl)、經取代或未經取代的吲唑基(indazolyl)、經取代或未經取代的啡噻基(phenothiazinyl)、經取代或未經取代的啡基(phenazinyl)、經取代或未經取代的咔唑基(carbazolyl)、經取代或未經取代的二苯并噻吩基(dibenzothiophenyl)、經取代或未經取代的咪唑基
(imidazolyl)、經取代或未經取代的***基(triazolyl)、經取代或未經取代的四唑基(tetrazolyl)、經取代或未經取代的二唑基(oxadiazolyl)、經取代或未經取代的***基(oxatriazolyl)、經取代或未經取代的噻***基(thiatriazolyl)、經取代或未經取代的苯并***(benzotriazolyl)、經取代或未經取代的吡基(pyrazinyl)、經取代或未經取代的嗒基(pyridazinyl)、經取代或未經取代的嘌呤基(purinyl)、經取代或未經取代的喹啉基(quinolinyl)、經取代或未經取代的異喹啉基(isoquinolinyl)、經取代或未經取代的呔基(phthalazinyl)、經取代或未經取代的萘啶基(naphpyridinyl)、經取代或未經取代的喹啉基(quinoxalinyl)、經取代或未經取代的喹唑啉基(quinazolinyl)、經取代或未經取代的吖啶基(acridinyl)或經取代或未經取代的啡啉基(phenanthrolinyl)。較佳的可用基團為經取代或未經取代的吡啶基、經取代或未經取代的嘧啶基、經取代或未經取代的三基、經取代或未經取代的噻吩基(thiophenyl)、經取代或未經取代的吡咯基、經取代或未經取代的苯并噻吩基(benzothiophenyl)、經取代或未經取代的吲哚基、經取代或未經取代的咪唑并[1,2-a]吡啶基、經取代或未經取代的苯并咪唑基、經取代或未經取代的吲唑基、經取代或未經取代的啡噻基、經取代或未經取代的啡基、經取代或未經取代的咔唑基或經取代或未經取代的二苯并噻吩基(dibenzothiophenyl)。
根據本發明較佳實施例,該用於有機EL元件的化合物為選自以下化學式所示化合物1至化合物31中之任一
者。
根據本發明實施例可提供一種有機電致發光(EL)元件,該有機電致發光(EL)元件包含本發明用於有機EL元件之化合物。
根據本發明實施例,有機EL元件可包含第一電極、第二電極及位在該第一電極與該第二電極之間的單個有機層或複數個有機層,且選自該單個有機層或該複數個有機層中的一個或更多個有機層可包含根據本發明之用於有機EL元件的化合物。
根據本發明實施例,該單個有機層或該複數個有機層可包含發光層。
根據本發明實施例,該複數個有機層可包含發光層,及該複數個有機層可進一步包含選自以下所述層中的一個或更多個層:電子注入層、電子傳遞層、電洞阻擋層、電子阻擋層、電洞傳遞層及電洞注入層。
根據本發明實施例,該發光層可包括主體(host)及摻雜劑(dopant)。
根據本發明實施例形成一種包含三聯苯基衍生物且該三聯苯基衍生物具有二芳基胺基的化合物,而可能提供各式各樣的衍生物,因此能調整該化合物的性質。當有機EL元件中含有此化合物時,能夠表現出各種性質。此外,可增進該有機EL元件的熱穩定性及發光效率,且使用該化合物作為電洞傳遞層材料能夠約束磷光發光材料的三重態激子,從而提升該有機EL元件的效率。
1‧‧‧有機EL元件
110‧‧‧第一電極
130‧‧‧有機層
131‧‧‧電子注入層
132‧‧‧電子傳遞層
133‧‧‧電洞阻擋層
134‧‧‧發光層
135‧‧‧電子阻擋層
136‧‧‧電洞傳遞層
137‧‧‧電洞注入層
150‧‧‧第二電極
搭配附圖閱讀以下詳細說明內容可更清楚瞭解本發明的上述及其他目的、特徵及優點,該等附圖中:第1圖圖示根據本發明實施例所做之有機EL元件的剖面圖;及第2圖圖示根據本發明另一實施例所做之有機EL元件的剖面圖。
本發明可做出各種修飾變化並可具有各種實施例,且意欲舉特定實施例以作說明。然而,以下說明內容並未將本發明限定於特定實施例,並應明白本發明涵蓋所有落入本發明精神與範圍內的變化態樣、均等物或替代物。此外,在描述本發明的內容中,當判斷本發明相關技術的詳細描述內容可能模糊掉本發明的實質內容時,對於該相關技術的描述將省略不提。
又,在以下說明內容中,「第一」、「第二」及諸如此類用語是用於區別某些構件與其他構件,但此等構件的
結構配置不應受限於該等用語。例如,在本發明範圍中,第一構件可能稱為第二構件,且第二構件可能稱為第一構件。
又,當提到任一構件「形成」或「疊置」在另一構件上時,該構件可能直接附接於另一構件的整個表面或一表面上,或可能有一附加構件額外插置在該兩構件之間。
除非另有說明,否則單數用語包括複數之意。在本申請案中,「包含」及「具有」是用來指出本案說明書中所描述之特徵、數字、步驟、操作、構件、部位或以上所述者之組合的存在,但並不排除可能有一個或更多個不同特徵、數字、步驟、操作、構件、部位或以上所述之組合的存在或額外增加一個或更多個不同特徵、數字、步驟、操作、構件、部位或以上所述之組合的可能性。
當用於本文中時,除非另有說明,否則「共價鍵(valence bond)」一詞意指單鍵、雙鍵或三鍵。
當用於本文中時,除非另有定義,否則「經取代(substituted)」一詞意指在取代基上或化合物上的至少一個氫被取代成氘、鹵素基團、羥基、氨基、C1至C30胺基、硝基、矽基、C1至C30烷基、C1至C30烷基矽基、C3至C30環烷基、C2至C30雜環烷基、C6至C30芳基、C1至C30雜芳基、C1至C20烷氧基、C1至C10三氟烷基或氰基。
此外,在該些經取代的鹵素基、羥基、氨基、C1至C30胺基、矽基、C1至C30烷基、C1至C30烷基矽基、C3至C30環烷基、C6至C30芳基、C1至C20烷氧基、C1至C10三氟烷基或氰基之中,兩相鄰的取代基可稠合而形成環。
當用於本文中,除非另有定義,否則「雜(hetero)」意指一官能基中含有1個~4個雜原子且其餘部分為碳,該等雜原子可選自於以下群組:N、O、S及P。
當用於本文中,除非另有定義,否則「以上所述者之組合(combination thereof)」意指兩個或更多個取代基藉由連接子而彼此連接在一起,或是兩個或更多個取代基彼此縮合(condensed)在一起。
當用於本文中,除非另有定義,否則「氫(hydrogen)」意指氫、氘或氚。
當用於本文中,除非另有定義,否則「烷基(alkyl group)」意指脂族烴基團。
該烷基可為不具有任何雙鍵或三鍵的「飽和烷基」。
該烷基可為具有至少一個雙鍵或三鍵的「不飽和烷基」。
「伸烯基(alkenylene group)」意指在至少兩個碳原子之間具有至少一個碳-碳雙鍵的官能基,及「伸炔基(alkynylene group)」意指在至少兩個碳原子之間具有至少一個碳-碳三鍵的官能基。不論該烷基是否飽和或不飽和,該烷基可為支鏈狀、直鏈狀或環狀。
該烷基可為C1至C30烷基,較佳為C1至C20烷基,更佳為C1至C10烷基,且最佳為C1至C6烷基。
例如,C1至C4烷基是指包含1個~4個碳原子的烷基鏈,尤其是選自以下群組中的烷基鏈:甲基、乙基、丙基、異丙基、正丁基、異丁基、仲丁基(sec-butyl)及叔丁基
(t-butyl)。
該烷基的具體實例包括甲基、乙基、丙基、異丙基、丁基、異丁基、叔丁基(t-butyl)、戊基、己基、乙烯基、丙烯基、丁烯基、環丙基、環丁基、環戊基、環己基,等等。
「胺基(amine group)」包括芳胺基、烷胺基、芳基烷胺基或烷基芳胺基。
「環烷基(cycloalkyl group)」一詞意指單環官能基或稠環型多環(即,共用相鄰碳原子對的環)官能基。
「雜環烷基(heterocycloalkyl group)」一詞意指含有1個~4個雜原子且其餘部分為碳的環烷基,該等雜原子可選自於以下群組:N、O、S及P。在雜環烷基是稠環的情況下,至少有一個環可含有1個~4個雜原子。
「芳香性基團(aromatic group)」一詞意指全部的環原子都具有p-軌域且這些p-軌域形成共軛作用的環狀官能基。芳香性基團的具體實例包括芳基及雜芳基。
「芳基(aryl group)」一詞意指單環官能基或稠環型多環(即,共用相鄰碳原子對的環)官能基。
「雜芳基(heteroaryl group)」一詞意指含有1個~4個雜原子且其餘部分為碳的芳基,該等雜原子可選自於以下群組:N、O、S及P。在雜芳基是稠環的情況下,至少有一個環可含有1個~4個雜原子。
在芳基及雜芳基中,環原子的數目是碳原子數與非碳原子數的總和。
當烷基與芳基組合使用而成為「烷基芳基」或「芳
基烷基」時,「烷基」及「芳基」分別具有以上所述之意義。
「芳基烷基」一詞意指具有芳基取代基的烷基(例如苄基)且歸屬於烷基。
「烷基芳基」一詞意指具有烷基取代基的芳基並歸屬於芳基。
以下參照附圖說明本發明之實施例,其中相同或相似的元件是以相同元件符號加以標示,並省略該等元件的重複說明。
參閱第1圖及第2圖,根據本發明實施例可提供一種有機EL元件1,該元件1包含本發明之用於有機EL元件的化合物。
根據本發明另一實施例,有機EL元件包括第一電極110、第二電極150及位在該第一電極與該第二電極之間的單個有機層或複數個有機層130,且選自於該單個有機層或該複數個有機層130中的一個或更多個有機層可包含本發明之用於有機EL元件的化合物。
如此,該單個有機層或該複數個有機層130可包含發光層134。
該複數個有機層130包含發光層134,且該複數個有機層130可進一步包含選自以下的一個或更多個層:電子注入層131、電子傳遞層132、電洞阻擋層133、電子阻擋層135、電洞傳遞層136及電洞注入層137。
該發光層134可包含主體及摻雜劑。
較佳利用透明基板支撐該有機EL元件。透明基板
的材料沒有特殊限制,只要該基板具有良好的機械強度、熱穩定性及透明度即可。基板的具體實例可包括玻璃、透明塑膠膜,等等。
根據本發明之有機EL元件的陽極(anode)材料可包括金屬、合金、導電化合物或上述材料之混合物,且該陽極材料具有4eV或更大的功函數。陽極材料的具體實例可包括Au金屬或透明導電材料,例如CuI、ITO(氧化銦錫)、SnO2及ZnO。陽極膜的厚度較佳設為10奈米~200奈米。
根據本發明之有機EL元件的陰極(cathode)材料可包括金屬、合金、導電化合物或上述材料之混合物,且該陰極材料具有小於4eV的功函數。陰極材料的具體實例可包括Na、Na-K合金、鈣、鎂、鋰、鋰合金、銦、鋁、鎂合金或鋁合金。此外,可使用鋁/AlO2、鋁/鋰、鎂/銀或鎂/銦。陰極膜的厚度較佳設為10奈米~200奈米。
為了提高有機EL元件的發光效率,一個或更多個電極較佳具有10%或更高的光透射率。該等電極的片電阻較佳為數百歐姆/毫米(Ω/mm)或更低。該等電極的厚度範圍在10奈米~1微米,且較佳為10奈米~400奈米。可藉由氣相沈積法(例如,化學氣相沈積法(CVD)、物理氣相沈積法(PVD)或諸如此類方法或濺射法)使用上述電極材料製造出薄膜形式的這類電極。
當使用本發明之用於有機EL元件的化合物並做調適以適用於本發明之該等目的時,已知的電洞傳遞材料、電洞注入材料、發光層材料、用於發光層的主體材料、電子傳
遞材料及電子注入材料可單獨用於各有機層中,或可與本發明用於有機EL元件的化合物做選擇性的組合使用。
電洞傳遞材料的實例可包括:卟啉化合物衍生物,包括N,N-二咔唑基-3,5-苯(N,N-dicarbazolyl-3,5-benzene,mCP)、聚(3,4-伸乙二氧噻吩):聚(苯乙烯磺酸)(poly(3,4-ethylenedioxythiophene):poly(styrenesulfonate),PEDOT:PSS)、N,N'-二(1-萘基)-N,N'-二苯基聯苯胺(N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine,NPD)、N,N'-二苯基-N,N'-二(3-甲基苯基)-4,4'-二氨基聯苯(N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl,TPD)、N,N'-二苯基-N,N'-二萘基-4,4'-二氨基聯苯(N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl)、N,N,N',N'-四-對-甲苯基-4,4'-二氨基聯苯(N,N,N',N'-tetra-p-tolyl-4,4'-diaminobiphenyl)、N,N,N'N'-四苯基-4,4'-二氨基聯苯(N,N,N'N'-tetraphenyl-4,4'-diaminobiphenyl)、1,10,15,20-四苯基-21H,23H-卟啉銅(II)(1,10,15,20-tetraphenyl-21H,23H-porphyrin copper(II)),等等;三芳胺衍生物,包括在主鏈或側鏈中具有芳族三級胺的聚合物、1,1-雙(4-二-對-甲苯基氨基苯基)環己基(1,1-bis(4-di-p-tolylaminophenyl)cyclohexane)、N,N,N-三(對-甲苯基)胺(N,N,N-tri(p-tolyl)amine)及4,4',4'-三[N-(3-甲基苯基)-N-苯胺基]三苯基胺(4,4',4'-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamin
e);咔唑衍生物,包括N-苯基咔唑(N-phenylcarbazole)及聚乙烯咔唑(polyvinylcarbazole);酞青衍生物,包括無金屬酞青及銅酞青;星爆狀胺(starburst amine)衍生物;烯胺-二苯乙烯(enaminestilbene)系的衍生物;含芳族三級胺之苯乙烯胺化合物的衍生物;聚矽烷,等等。
電子傳遞材料的實例可包括二苯基膦氧基-4-(三苯基矽基)苯(diphenylphosphine oxide-4-(triphenylsilyl)phenyl,TSPO1)、Alq3、2,5-二芳基矽雜環戊二烯衍生物(2,5-diaryl sylol derivatives,PyPySPyPy)、全氟化合物(PF-6P)、八取代環辛四烯化合物(COTs),等等。
在根據本發明的有機EL元件中,可採用在單層中含有一種或更多種上述化合物的形式或可採用含有不同化合物之複數個堆疊層的形式來提供電子注入層、電子傳遞層、電洞傳遞層及電洞注入層。
該發光材料可包括,例如,光致發光性螢光材料、螢光增亮劑、雷射染料、有機閃爍劑及螢光分析劑。此等材料的具體實例包括:咔唑系化合物;氧化膦系化合物;咔唑系氧化膦化合物;聚芳族化合物,包括雙((3,5-二氟-4-氰基苯基)吡啶)吡啶甲酸銥(bis((3,5-difluoro-4-cyanophenyl)pyridine)iridium picolinate,FCNIrpic)、三(8-羥喹啉)鋁(tris(8-hydroxyquinoline)aluminum,Alq3)、蒽(anthracene)、菲(phenanthrene)、芘(pyrene)、(chrysene)、苝(perylene)、蔻(coronene)、紅螢烯(rubrene)及喹吖啶酮(quinacridone);寡
聚伸苯化合物,包括四聚伸苯(quaterphenyl);用於液體閃爍作用的閃爍劑,包括1,4-雙(2-甲基苯乙烯基)苯(1,4-bis(2-methylstyryl)benzene)、1,4-雙(4-甲基苯乙烯基)苯、1,4-雙(4-甲基-5-苯基-2-唑基)苯(1,4-bis(4-methyl-5-phenyl-2-oxazolyl)benzene)、1,4-雙(5-苯基-2-唑基)苯(1,4-bis(5-phenyl-2-oxazolyl)benzene)、2,5-雙(5-叔丁基-2-苯并唑基)噻吩(2,5-bis(5-t-butyl-2-benzoxazolyl)thiophene)、1,4-二苯基-1,3-丁二烯(1,4-diphenyl-1,3-butadiene)、1,6-二苯基-1,3,5-己三烯(1,6-diphenyl-1,3,5-hexatriene)及1,1,4,4-四苯基-1,3-丁二烯(1,1,4,4-tetraphenyl-1,3-butadiene);羥喹啉(oxine)衍生物的金屬錯合物;香豆素染料(coumarine dyes)、二氰亞甲基哌喃染料(dicyanomethylenepyran dyes)、二氰亞甲基噻喃染料(dicyanomethylenethiopyran dyes)、聚次甲基染料(polymethine dyes)、苯并蒽酮染料(oxobenzanthracene dyes)、染料(xanthene dyes)、喹啉酮染料(carbostyryl dyes)、苝染料(perylene dyes)、化合物(oxazine compounds)、二苯乙烯衍生物(stilbene derivatives)、螺環化合物(spiro compounds)、二唑化合物(oxadiazole compounds),等等。
可使用已知製程(例如真空沈積法、旋塗法或旋轉模鑄法)以薄膜形式提供本發明之有機EL元件的各層,或可使用各層材料製造本發明之有機EL元件的各層。各層的厚度沒有具體限制,但可根據材料性質做適當的設定,且厚度範圍通常可在2奈米~5000奈米間。
由於本發明用於有機EL元件的化合物可進行真空沈積,因此薄膜形成製程簡單,且可輕易獲得實質上無小孔的均勻薄膜。
透過以下實施例的舉例說明,可瞭解如何合成該用於有機EL元件的化合物及製造含有該化合物的有機EL元件,從而更佳地瞭解本發明,但不應將該等實施例視為是本發明的限制。
[實施例]
製備實施例1:合成中間產物1
在處於氮氣環境下的250毫升圓底三頸燒瓶中,置入12.0克的1,3-二溴-5-碘苯(1,3-dibromo-5-iodobenzene)、9.5克的N-苯基咔唑-3-硼酸(N-phenylcarbazole-3-boronic acid)、1.2克的四(三苯基膦)鈀(0)(tetrakis(triphenylphosphine)palladium(0))、9克的碳酸鉀(potassium carbonate)、120毫升的甲苯(toluene)及30毫升的甲醇(methanol),並於80℃攪拌6小時。待該反應溶液冷卻,且隨後以二氯甲烷及水萃取該反應溶液,並濃縮該萃取溶
液。使用二氯甲烷與正-己烷所形成的溶劑混合物使該溶液進行管柱層析,並濃縮該經管柱層析的溶液,從而獲得9.3克的中間產物1(產率62%)。
1H NMR(CDCl3,600MHz)δ 8.28(s,1H),8.20-8.18(d,1H),7.8-7.76(s,2H),7.63-7.62(m,3H),7.58-7.55(m,3H),7.51-7.48(t,1H),7.45-7.40(m,3H),7.34-7.3(t,1H)。
製備實施例2:合成中間產物2
在處於氮氣環境下的250毫升圓底三頸燒瓶中,置入8克的1,3,5-三溴苯(1,3,5-tribromobenzene)、5克的二苯并呋喃基-4-硼酸(dibenzofuanyl-4-boronic acid)、0.3克的四(三苯基膦)鈀(0)、9克的碳酸鉀、120毫升的四氫呋喃(tetrahydrofuran)及30毫升的水,並於60℃攪拌6小時。待該反應溶液冷卻,且隨後以二氯甲烷及水萃取該反應溶液,並濃縮該萃取溶液。使用二氯甲烷與正-己烷所形成的溶劑混合物使該溶液進行管柱層析,並濃縮該經管柱層析的溶液,從而獲得6.3克的中間產物2(產率66%)。
1H NMR(CDCl3,600MHz)δ 8.01-7.95(m,4H),7.72(s,1H),7.66-7.63(d,1H),7.56-7.53(d,1H),7.52-7.48(dd,1H),7.45-7.42(dd,1H),7.41-7.36(dd,1H)。
製備實施例3:合成中間產物3
在處於氮氣環境下的250毫升圓底三頸燒瓶中,置入4克的4-溴聯苯(4-bromobiphenyl)、3.1克的對-甲苯胺(p-toluidine)、0.3克的三(二亞苄基丙酮)二鈀(0)(tris(dibenzylideneacetone)dipalladium(0))、4.2克的叔丁醇鈉(sodium tert-butoxide)、0.1克的三叔丁基膦(Tri-tert-butylphosphine)及120毫升的甲苯,並於110℃攪拌8小時。待該反應溶液冷卻,且隨後以二氯甲烷及水萃取該反應溶液,並濃縮該萃取溶液。使用二氯甲烷與正-己烷所形成的溶劑混合物使該溶液進行管柱層析,並濃縮該經管柱層析的溶液,從而獲得4.3克的中間產物3(產率97%)。
1H NMR(CDCl3,600MHz)δ 7.59-7.54(d,2H),7.53-7.46(d,2H),7.43-7.39(dd,2H),7.32-7.27(t,1H),7.15-7.00(m,6H),2.32(s,3H)。
製備實施例4:合成中間產物4
在處於氮氣環境下的250毫升圓底三頸燒瓶中,置入4克之在製備實施例3中所合成的中間產物3、5.2克的4-溴碘苯(4-bromo iodobenzene)、0.2克的三(二亞苄基丙酮)二鈀(0)、3.3克的叔丁醇鈉、0.2克的三苯基膦(triphenylphosphine)及60毫升的甲苯,並於110℃攪拌8小時。待該反應溶液冷卻,且隨後以二氯甲烷及水萃取該反應溶液,並濃縮該萃取溶液。使用二氯甲烷與正-己烷所形成的溶劑混合物使該溶液進行管柱層析,並濃縮該經管柱層析的溶液,從而獲得4.3克的中間產物4(產率67%)。
1H NMR(CDCl3,600MHz)δ 7.60-7.54(d,2H),7.51-7.46(d,2H),7.45-7.39(dd,2H),7.36-7.27(m,3H),7.15-7.00(m,6H),6.99-6.95(d,2H),2.33(s,3H)。
製備實施例5:合成中間產物5
在處於氮氣環境下的100毫升圓底三頸燒瓶中,置入4克之在製備實施例4中所合成的中間產物4、4.8克的聯硼酸頻那醇酯(bis(pinacolato)diboron)、0.2克的1,1’-雙(二苯基膦基二茂鐵)二氯化鈀(II)(1,1’-bis(diphenylphosphinoferrocene)dichloropalladium(II))、2.9克的乙酸鉀及60毫升的二甲基亞碸(DMSO),並於110。℃攪拌8小時。待該反應溶液冷卻,且隨後以二氯甲烷及水萃取該反應溶液,並濃縮該萃取溶液。使用二氯甲烷與正-己烷所形成的溶劑混合物使該溶液進行管柱層析,並濃縮該經管柱層析的溶液,從而獲得4.1克的中間產物5(產率91%)。
1H NMR(CDCl3,600MHz)δ 7.70-7.66(m,2H),7.58-7.53(d,2H),7.48-7.43(m,2H),7.42-7.37(dd,2H),7.31-7.27(t,1H),7.16-7.12(m,2H),7.11-7.03(m,6H),2.32(s,3H),1.33(s,12H)。
實施例1:合成化合物6
在處於氮氣環境下的100毫升圓底三頸燒瓶中,置入4克之在製備實施例1中所合成的中間產物1、5.4克的4-(二苯基氨基)苯硼酸(4-(diphenylamino)phenylboronic acid)、0.6克的四(三苯基膦)鈀(0)、4.6克的碳酸鉀及50毫升的甲苯及20毫升的甲醇,並於80℃攪拌6小時。待該反應溶液冷卻,且隨後以二氯甲烷及水萃取該反應溶液,並濃縮該萃取溶液。使用二氯甲烷與正-己烷所形成的溶劑混合物使該溶液進行管柱層析,並濃縮該經管柱層析的溶液,從而獲得2.6克的化合物6(產率40%)。
1H NMR(CDCl3,600MHz)δ 8.33(s,1H),8.17-8.16(d,1H),7.8-7.76(s,2H),7.63-7.58(m,7H),7.53(s,2H),
7.47-7.44(t,1H),7.42-7.41(d,6H),7.31-7.30(t,1H),7.16(s,1H),7.13-7.12(d,2H),7.07(s,2H),7.04-7.00(m,15H),6.97-6.96(d,2H)。
液相層析/質譜儀(LC/Mass)[M+H]+:805.3
實施例2:合成化合物17
用實施例1中所述的相同方法,但改用中間產物2及4-[二(甲苯基)氨基]苯硼酸(4-(ditolyl amino)phenyl boronic acid)來代替中間產物1及4-(二苯基氨基)苯硼酸,而獲得3.5克的化合物17(產率:45%)。
1H NMR(CDCl3,600MHz)δ 8.01-7.98(m,3H),7.98-7.95(d,1H),7.80-7.78(d,1H),7.70-7.68(d,1H),7.62-7.60(d,1H),7.59-7.56(d,4H),7.48-7.43(m,2H),7.38-7.34(t,1H),7.14-7.10(d,4H),7.10-7.04(m,16H),2.32(s,12H)。
液相層析/質譜儀[M+H]+:786.3
實施例3:合成化合物18
用實施例1中所述的相同方法,但改用中間產物2及中間產物5來代替中間產物1及4-(二苯基氨基)苯硼酸,而獲得5.2克的化合物18(產率:57%)。
1H NMR(CDCl3,600MHz)δ 8.05-8.03(m,2H),8.02-7.99(d,1H),7.98-7.96(d,1H),7.83(s,1H),7.72-7.69(d,1H),7.65-7.61(m,5H),7.60-7.56(d,4H),7.51-7.40(m,10H),7.39-7.35(t,1H),7.33-7.29(t,2H),7.23-7.18(m,8H),7.15-7.10(m,8H),2.35(s,6H)。
液相層析/質譜儀[M+H]+:910.4
元件實施例1:製造含有化合物6以作為第二電洞
傳遞層的有機EL元件
使用異丙醇溶劑對塗有厚度100奈米之ITO(氧化銦錫)薄膜的玻璃基板進行超音波震盪清洗,乾燥該基板,將該基板置入電漿清洗系統中以利用氧電漿清洗該基板5分鐘,且隨後將該基板傳送至真空沈積系統內。
以此方式準備好的ITO透明電極是用來作為陽極(anode),並在該ITO基板上真空沈積N,N'-二苯基-N,N'-雙-[4-(苯基-間-甲苯基氨基)-苯基]-聯苯-4,4'-二胺(N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolylamino)-phenyl]-biphenyl-4,4'-diamine,DNTPD),從而形成具有50奈米之厚度的電洞注入層。隨後,真空沈積厚度30奈米的N,N,N’,N’-四(4-聯苯基)-二氨基聯苯(N,N,N',N'-tetra(4-biphenyl)-diaminobiphenylene,TBDB),從而形成第一電洞傳遞層,及使用化合物6在該第一電洞傳遞層上形成厚度10奈米的第二電洞傳遞層。在該電洞傳遞層上真空沈積GH1(作為主體)及6%的GD1(作為摻雜劑)達30奈米的厚度,從而形成發光層。
之後,在該發光層上模鑄厚度10奈米的GH1以作為電洞阻擋層。使用三(8-羥基喹啉)鋁(tris(8-quinolinolato)aluminum(III),Alq3)在該電洞阻擋層上形成厚度20奈米的電子傳遞層。在該電子傳遞層上依序真空沈積2奈米厚的羥喹啉鋰(lithium quinolate,Liq)及100奈米厚的鋁(Al)以形成陰極(cathode),從而製造出有機EL元件。
元件實施例2:製造含有化合物17以作為第二電洞傳遞層的有機EL元件
以元件實施例1中所示的相同方式製造有機EL元件,但改用化合物17代替化合物6作為第二電洞傳遞層。
元件實施例3:製造含有化合物18以作為第二電洞傳遞層的有機EL元件
以元件實施例1中所示的相同方式製造有機EL元件,但改用化合物18代替化合物6作為第二電洞傳遞層。
比較元件實例1:製造含有TBDB以作為第二電洞傳遞層的有機EL元件
以元件實施例1中所示的相同方式製造有機EL元件,但改用TBDB代替化合物6作為第二電洞傳遞層。
該等元件實施例及比較元件實例中所使用之DNTPD、TBDB、GH1、GH2、GD1及Alq3的化學式如以下所示:
以1000燭光/平方公尺(cd/m2)的亮度對元件實施例1至元件實施例3及比較元件實例1中所製成之有機EL元件的性質進行評估。該等結果顯示於以下表1中。
電流密度
在所製成的有機EL元件中,當電壓從0伏特(V)升高到10伏特時,使用電流-電壓計(Keithley 2635A Source Meter)測量每個單位元件的電流,並將所測得的電流值除以面積,從而獲得電流密度。
亮度效率
在所製成的有機EL元件中,當電壓從0伏特升高到10伏特時,使用亮度計(Minolta CS-2000)測量亮度,並將所測得的亮度值除以該電流值,從而得到亮度效率(brightness
efficiency)。
色座標
使用亮度計(Minolta CS-2000)測量色座標。
根據表1,從該等結果可明顯看出,與使用傳統材料TBDB的情況相較之下,使用本發明之化合物6、化合物17及化合物18作為第二電洞傳遞層的材料來製造有機EL元件時,該等有機EL元件皆展現卓越性能、電流密度降低及亮度效率提高。
儘管已揭示本發明的較佳實施例作為示範說明之用,然而所屬技術領域中熟習該項技藝者將領會到在不偏離後附請求項中所揭示的本發明精神及範圍下可能做出各種修飾、添加及替代。
Claims (12)
- 一種用於一有機電致發光元件的化合物,該化合物如以下化學式4或化學式6所示:其中X1及X3為彼此相同或互不相同,且X1及X3各自獨立地為氧原子、硫原子、或Ar2是一經取代或未經取代的C1至C30烷基、一經取代或未經取代的C3至C30環烷基、一經取代或未經取代的C2至C30雜環烷基、一經取代或未經取代的C6至C30芳基或一經取代或未經取代的C1至C30雜芳基;R22及R23彼此相同或互不相同,且R22及R23各自獨立地為氫原子、一經取代或未經取代的C1至C30烷基、一經取代或未經取代的C3至C30環烷基、一經取代或未經取代的C2至C30雜環烷基、一經取代或未經取代的C6至C30芳基或一經取代或未經取代的C1至C30雜芳基;R2至R13為彼此相同或互不相同,且R2至R13各自獨立地為氫原子、一經取代或未經取代的C1至C30烷基、一經取代或未經取代的C3至C30環烷基、一經取代或未經取代的C2至C30雜環烷基、一經取代或未經取代的C6至C30芳基或一經取代或未經取代的C1至C30雜芳基,或R2至R13其中至少一者進一步與其所連接之一碳原子旁邊的一碳原子耦合以形成一經取代或未經取代的C3至C30稠合環烷基、一經取代或未經取代的C2至C30稠合雜環烷基、一經取代或未經取代的C6至C30稠合芳基或一經取代或未經取代的C1至C30稠合雜芳基;及R14至R16及R20至R21為彼此相同或互不相同,且R14至R16及R20至R21各自獨立地為氫原子、一經取代或未經取代的C1至C30烷基、一經取代或未經取代的C3至C30環烷基、一經取代或未經取代的C2至C30雜環烷基、一經取代或未經取代的C6至C30芳基或一經取代或未經取代的C1至C30雜芳基。
- 如請求項1所述之化合物,其中R14至R16為彼此相同或互不相同,且R14至R16各自獨立地為氫原子、 、一經取代或未經取代的C1至C30烷基、一經取代或未經取代的C3至C30環烷基或一經取代或未經取代的C2至C30雜環烷基;X4為氧原子、硫原子、或Ar3是一經取代或未經取代的C1至C30烷基、一經取代或未經取代的C3至C30環烷基、一經取代或未經取代的C2至C30雜環烷基、一經取代或未經取代的C6至C30芳基或一經取代或未經取代的C1至C30雜芳基;R29及R30彼此相同或互不相同,且R29及R30各自獨立地為氫原子、一經取代或未經取代的C1至C30烷基、一經取代或未經取代的C3至C30環烷基、一經取代或未經取代的C2至C30雜環烷基、一經取代或未經取代的C6至C30芳基或一經取代或未經取代的C1至C30雜芳基;及R24至R28彼此相同或互不相同,且R24至R28各自獨立地為氫原子、一經取代或未經取代的C1至C30烷基、一經取代或未經取代的C3至C30環烷基、一經取代或未經取代的C2至C30雜環烷基、一經取代或未經取代的C6至C30芳基或一經取代或未經取代的C1至C30雜芳基。
- 如請求項1所述之化合物,其中R2至R13彼此相同或互不相同,且R2至R13各自獨立地為氫原子、一經取代或未經取代的C1至C30烷基、一經取代或未經取代的C3至C30環烷基、一經取代或未經取代的C2至C30雜環烷基、一經取代或未經取代的C6至C30芳基或一經取代或未經取代的C1至C30雜芳基。
- 一種有機電致發光元件,該有機電致發光元件包含請求項1所述之化合物。
- 一種有機電致發光元件,該有機電致發光元件包含一第一電極、一第二電極及位在該第一電極與該第二電極之間的一單個有機層或複數個有機層,其中選自該單個有機層或該複數個有機層中的一個或更多個有機層包含請求項1所述之化合物。
- 如請求項9所述之有機電致發光元件,其中該單個有機層或該複數個有機層包含一發光層。
- 如請求項9所述之有機電致發光元件,其中該複數個有機層包含一發光層,及該複數個有機層進一步包含選自以下所述層中的一個或更多個層:電子注入層、電子傳遞層、電洞阻擋層、電子阻擋層、電洞傳遞層及電洞注入層。
- 如請求項10所述之有機電致發光元件,其中該發光層包括一主體及一摻雜劑。
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JPH10237438A (ja) * | 1997-02-28 | 1998-09-08 | Idemitsu Kosan Co Ltd | 有機電界発光素子 |
JP2000247932A (ja) * | 1999-03-01 | 2000-09-12 | Minolta Co Ltd | 新規アミノ化合物とその製造方法、および用途 |
JP2009016718A (ja) * | 2007-07-09 | 2009-01-22 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
TW201247840A (en) * | 2011-04-01 | 2012-12-01 | Duksan High Metal Co Ltd | Compound, organic electronic element using the same, and electronic device thereof |
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JPH10237438A (ja) * | 1997-02-28 | 1998-09-08 | Idemitsu Kosan Co Ltd | 有機電界発光素子 |
JP2000247932A (ja) * | 1999-03-01 | 2000-09-12 | Minolta Co Ltd | 新規アミノ化合物とその製造方法、および用途 |
JP2009016718A (ja) * | 2007-07-09 | 2009-01-22 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
TW201247840A (en) * | 2011-04-01 | 2012-12-01 | Duksan High Metal Co Ltd | Compound, organic electronic element using the same, and electronic device thereof |
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WO2015026053A1 (en) | 2015-02-26 |
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