JPWO2009008099A1 - 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 - Google Patents
有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 Download PDFInfo
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- JPWO2009008099A1 JPWO2009008099A1 JP2009522493A JP2009522493A JPWO2009008099A1 JP WO2009008099 A1 JPWO2009008099 A1 JP WO2009008099A1 JP 2009522493 A JP2009522493 A JP 2009522493A JP 2009522493 A JP2009522493 A JP 2009522493A JP WO2009008099 A1 JPWO2009008099 A1 JP WO2009008099A1
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- carbon atoms
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- phenanthrolin
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- 239000000463 material Substances 0.000 title claims abstract description 79
- 238000005401 electroluminescence Methods 0.000 title claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 70
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 22
- 239000010409 thin film Substances 0.000 claims abstract description 19
- 230000005525 hole transport Effects 0.000 claims abstract description 16
- 150000004696 coordination complex Chemical class 0.000 claims abstract description 9
- -1 9-carbazolyl group Chemical group 0.000 claims description 1397
- 125000001424 substituent group Chemical group 0.000 claims description 220
- 125000004432 carbon atom Chemical group C* 0.000 claims description 181
- 125000003118 aryl group Chemical group 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 238000002347 injection Methods 0.000 claims description 33
- 239000007924 injection Substances 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000004104 aryloxy group Chemical group 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 17
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 17
- 125000005110 aryl thio group Chemical group 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 239000002019 doping agent Substances 0.000 claims description 15
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- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 12
- 125000001769 aryl amino group Chemical group 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 10
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 10
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 8
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- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
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- 229910052697 platinum Inorganic materials 0.000 claims description 3
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- 230000007547 defect Effects 0.000 abstract description 8
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 12
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- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 238000000034 method Methods 0.000 description 8
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- 239000007787 solid Substances 0.000 description 8
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 7
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 7
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- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
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- 239000000460 chlorine Substances 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 229910052763 palladium Inorganic materials 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 238000000859 sublimation Methods 0.000 description 7
- 230000008022 sublimation Effects 0.000 description 7
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 6
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 6
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 6
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 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 6
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 6
- 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 6
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 5
- 125000006083 1-bromoethyl group Chemical group 0.000 description 5
- 125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 description 5
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 5
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 5
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 5
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 5
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 5
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 5
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 5
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 5
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 5
- 125000000732 arylene group Chemical group 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 230000002950 deficient Effects 0.000 description 5
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 5
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- 125000005999 2-bromoethyl group Chemical group 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
- 0 CCc1c(CC*)[n](C)c(I)n1 Chemical compound CCc1c(CC*)[n](C)c(I)n1 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
- 101100457453 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) MNL1 gene Proteins 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 150000001342 alkaline earth metals Chemical class 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 125000005997 bromomethyl group Chemical group 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 230000005281 excited state Effects 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 125000005647 linker group Chemical group 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 4
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 150000002910 rare earth metals Chemical class 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
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- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical group C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 229910018068 Li 2 O Inorganic materials 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910001508 alkali metal halide Inorganic materials 0.000 description 3
- 150000008045 alkali metal halides Chemical class 0.000 description 3
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 229910052792 caesium Inorganic materials 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 208000027386 essential tremor 1 Diseases 0.000 description 3
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 3
- 229910052738 indium Inorganic materials 0.000 description 3
- 150000002484 inorganic compounds Chemical class 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 239000012212 insulator Substances 0.000 description 3
- 150000002503 iridium Chemical class 0.000 description 3
- 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 description 3
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 3
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- 238000010183 spectrum analysis Methods 0.000 description 3
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- 150000003852 triazoles Chemical group 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 2
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 2
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- 125000004958 1,4-naphthylene group Chemical group 0.000 description 2
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- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 2
- 125000004134 1-norbornyl group Chemical group [H]C1([H])C([H])([H])C2(*)C([H])([H])C([H])([H])C1([H])C2([H])[H] 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- 125000006280 2-bromobenzyl group Chemical group [H]C1=C([H])C(Br)=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
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- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 2
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- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical group C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 2
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- 125000006483 4-iodobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1I)C([H])([H])* 0.000 description 2
- 125000005803 6,12-chrysenylene group Chemical group [H]C1=C([H])C2=C(C([H])=C1[H])C1=C([H])C([*:2])=C3C([H])=C([H])C([H])=C([H])C3=C1C([H])=C2[*:1] 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
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- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- 229910052769 Ytterbium Inorganic materials 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
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- 230000008021 deposition Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
- 125000005368 heteroarylthio group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 150000002475 indoles Chemical group 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004971 nitroalkyl group Chemical group 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 150000002907 osmium Chemical class 0.000 description 1
- CQDAMYNQINDRQC-UHFFFAOYSA-N oxatriazole Chemical group C1=NN=NO1 CQDAMYNQINDRQC-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- KELCFVWDYYCEOQ-UHFFFAOYSA-N phenanthridin-1-ol Chemical compound C1=CC=CC2=C3C(O)=CC=CC3=NC=C21 KELCFVWDYYCEOQ-UHFFFAOYSA-N 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound 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
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000006410 propenylene group Chemical group 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- YGNGABUJMXJPIJ-UHFFFAOYSA-N thiatriazole Chemical group C1=NN=NS1 YGNGABUJMXJPIJ-UHFFFAOYSA-N 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 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
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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Abstract
Description
特許文献7,8には、ジベンゾ化合物にカルバゾリル骨格を結合させた化合物群が記載されている。青色系りん光素子のホスト材料として実施例に記載されているが、本発明のような化合物群に関しては記載が無く、効果も不明である。
特許文献9,10,11には同様にジベンゾ化合物とアントラセン骨格との結合化合物が記載されている。しかしながらこれらの化合物はアントラセン骨格を有しているため,3重項の励起状態のエネルギーレベルが小さく,これらの化合物群のどれを発光層のホスト材料として用いても,青色系りん光発光材料を発光させることができない。
また,特許文献12には少なくとも2つの重合性官能基が必須であるジベンゾフラン骨格を有する化合物が記載されている。しかし、2重結合、3重結合等の不飽和結合で置き換えられることにより形成される基,例えば、プロペニレン基、ビニレン基、4−プロピル−2−ペンテニレン基等のような重合性置換基をりん光発光素子のホスト材料の分子骨格に組み込んだ場合,素子内でラジカルが連鎖的に発生し,発光効率,寿命に悪い影響を及ぼすことが懸念される。
R6とR10は、それぞれ独立に、水素原子または置換基を有してもよい炭素数1〜40のアルキル基であり、
R7〜R9は、それぞれ独立に、水素原子、ハロゲン原子、置換基を有してもよい炭素数1〜40のアルキル基、置換基を有してもよい炭素数3〜15のシクロアルキル基、置換基を有してもよい炭素数3〜20の複素環基、置換基を有してもよい炭素数1〜40のアルコキシ基、置換基を有してもよい炭素数6〜40の非縮合アリール基、置換基を有してもよい炭素数10〜18の縮合アリール基、置換基を有してもよい炭素数6〜20のアリールオキシ基、置換基を有してもよい炭素数7〜20のアラルキル基、置換基を有してもよい炭素数6〜40のアリールアミノ基、置換基を有してもよい炭素数1〜40のアルキルアミノ基、置換基を有してもよい炭素数7〜60のアラルキルアミノ基、置換基を有してもよい炭素数7〜40のアリールカルボニル基、置換基を有してもよい炭素数6〜20のアリールチオ基、置換基を有してもよい炭素数1〜40のハロゲン化アルキル基、または、シアノ基である、但し、R8とR9またはR8とR7が互いに結合して環構造を形成しない場合、R7〜R9の少なくとも1つは置換基を有してもよい9−カルバゾリル基、置換基を有してもよい窒素原子数2〜5のアザカルバゾリル基、置換基を有してもよいジベンゾフラニル基、置換基を有してもよいジベンゾチオフェニル基、または、置換基を有してもよいフェニル基またはビフェニル基であり、該フェニル基またはビフェニル基は、置換基を有してもよい9−カルバゾリル基、置換基を有してもよい窒素原子数2〜5のアザカルバゾリル基、置換基を有してもよいジベンゾフラニル基、および、置換基を有してもよいジベンゾチオフェニル基から選ばれる少なくとも1つの基で置換されており、
R8とR9またはR8とR7は互いに結合して置換基を有してもよい環構造を形成してもよく、該環構造を形成しないR7またはR9は水素原子、ハロゲン原子、置換基を有してもよい炭素数1〜40のアルキル基、置換基を有してもよい炭素数3〜15のシクロアルキル基、置換基を有してもよい炭素数3〜20の複素環基、置換基を有してもよい炭素数1〜40のアルコキシ基、置換基を有してもよい炭素数6〜40の非縮合アリール基、置換基を有してもよい炭素数10〜18の縮合アリール基、置換基を有してもよい炭素数6〜20のアリールオキシ基、置換基を有してもよい炭素数7〜20のアラルキル基、置換基を有してもよい炭素数6〜40のアリールアミノ基、置換基を有してもよい炭素数1〜40のアルキルアミノ基、置換基を有してもよい炭素数7〜60のアラルキルアミノ基、置換基を有してもよい炭素数7〜40のアリールカルボニル基、置換基を有してもよい炭素数6〜20のアリールチオ基、置換基を有してもよい炭素数1〜40のハロゲン化アルキル基、または、シアノ基である、但し、R8とR9またはR8とR7とそれらが結合しているベンゼン環がカルバゾリル基を形成する場合は除く、
R7〜R9のいずれかが置換基を有してもよいジベンゾフラニル基または置換基を有してもよいジベンゾチオフェニル基である場合、R1〜R3のすべては水素原子であり、
R1〜R3およびR6〜R10の各置換基は末端に重合性官能基を有することはなく、
Xは、硫黄原子または酸素原子である]。
前記アルカリ土類金属としては、Ca(仕事関数:2.9eV)、Sr(仕事関数:2.0〜2.5eV)、Ba(仕事関数:2.52eV)等が挙げられ、仕事関数が2.9eV以下のものが特に好ましい。
前記希土類金属としては、Sc、Y、Ce、Tb、Yb等が挙げられ、仕事関数が2.9eV以下のものが特に好ましい。
以上の金属のうち好ましい金属は特に還元能力が高く、電子注入域への比較的少量の添加により、有機EL素子の発光輝度の向上や長寿命化が可能になる。
前記アルカリ土類金属化合物としては、BaO、SrO、CaO及びこれらを混合したBaxSr1-xO(0<x<1)、BaxCa1-xO(0<x<1)等が挙げられ、BaO、SrO、CaOが好ましい。
前記希土類金属化合物としては、YbF3、ScF3、ScO3、Y2O3、Ce2O3、GdF3、TbF3等が挙げられ、YbF3、ScF3、TbF3が好ましい。
還元性ドーパントを層状に形成する場合は、界面の有機層を発光材料や電子注入材料により層状に形成した後に、還元ドーパントを単独で抵抗加熱蒸着法により蒸着し、好ましくは層の厚み0.1〜15nmで形成する。
還元性ドーパントを島状に形成する場合は、界面の有機層を発光材料や電子注入材料により島状に形成した後に、還元ドーパントを単独で抵抗加熱蒸着法により蒸着し、好ましくは島の厚み0.05〜1nmで形成する。
また、本発明の有機EL素子における、主成分である発光材料や電子注入材料と還元性ドーパントの割合としては、モル比で主成分:還元性ドーパント=5:1〜1:5であると好ましく、2:1〜1:2であるとさらに好ましい。
ハロゲン原子の例としては、前記と同様のものが挙げられる。また、置換されていてもよいアミノ基の例としては、前記アルキルアミノ基、アリールアミノ基、アラルキルアミノ基と同様のものが挙げられる。
炭素数1〜40の炭化水素基としては、アルキル基、アルケニル基、シクロアルキル基、アルコキシ基、アリール基、複素環基、アラルキル基、アリールオキシ基、アルコキシカルボニル基等が挙げられ、それぞれ置換されていてもよい。該アルキル基、アルケニル基、シクロアルキル基、アルコキシ基、アリール基、複素環基、アラルキル基、およびアリールオキシ基の例としては、前記と同様のものが挙げられ、アルコキシカルボニル基は−COOY’と表され、Y’の例としては前記アルキル基と同様のものが挙げられる。
式(A)のLは、下記一般式(A’)又は(A'')で表される基である。
LBがアリール基または芳香族複素環基である場合、置換基を有していてもよい。該置換基としては、好ましくはアルキル基、アルケニル基、アルキニル基、アリール基、アミノ基、アルコキシ基、アリールオキシ基、アシル基、アルコキシカルボニル基、アリールオキシカルボニル基、アシルオキシ基、アシルアミノ基、アルコキシカルボニルアミノ基、アリールオキシカルボニルアミノ基、スルホニルアミノ基、スルファモイル基、カルバモイル基、アルキルチオ基、アリールチオ基、スルホニル基、ハロゲン原子、シアノ基、芳香族複素環基であり、より好ましくはアルキル基、アリール基、アルコキシ基、アリールオキシ基、ハロゲン原子、シアノ基、芳香族複素環基であり、さらに好ましくはアルキル基、アリール基、アルコキシ基、アリールオキシ基、芳香族複素環基であり、特に好ましくはアルキル基、アリール基、アルコキシ基、芳香族複素環基である。
RB2の脂肪族炭化水素基は、直鎖、分岐又は環状のアルキル基(好ましくは炭素数1〜20、より好ましくは炭素数1〜12、特に好ましくは炭素数1〜8のアルキル基であり、例えば、メチル、エチル、イソプロピル、t−ブチル、n−オクチル、n−デシル、n−ヘキサデシル、シクロプロピル、シクロペンチル、シクロヘキシル等が挙げられる。)、アルケニル基(好ましくは炭素数2〜20、より好ましくは炭素数2〜12、特に好ましくは炭素数2〜8のアルケニル基であり、例えば、ビニル、アリル、2−ブテニル、3−ペンテニル等が挙げられる。)、アルキニル基(好ましくは炭素数2〜20、より好ましくは炭素数2〜12、特に好ましくは炭素数2〜8のアルキニル基であり、例えば、プロパルギル、3−ペンチニル等が挙げられる。)であり、アルキル基であると好ましい。
RB2として好ましくは脂肪族炭化水素基、アリール基又は複素環基であり、より好ましくは脂肪族炭化水素基又はアリール基(好ましくは炭素数6〜30、より好ましくは炭素数6〜20、さらに好ましくは炭素数6〜12)であり、さらに好ましくは脂肪族炭化水素基(好ましくは炭素数1〜20、より好ましくは炭素数1〜12、さらに好ましくは炭素数2〜10)である。
nB2は、1〜6の整数、好ましくは1〜4の整数、より好ましくは2または3である。
ZB71、ZB72及びZB73は、それぞれ一般式(B)におけるZB2と同様であり、また好ましい範囲も同様である。
LB71、LB72及びLB73は、それぞれ単結合または一般式(B)における二価のLBと同様であり、好ましくは、単結合、二価の芳香族炭化水素環基、二価の芳香族複素環基、及びこれらの組み合わせからなる二価の連結基であり、より好ましくは単結合である。LB71、LB72及びLB73は置換基を有していてもよく、置換基としては前記一般式(B)におけるLBで表される基の置換基として挙げたものと同様であり、また好ましい置換基も同様である。
Yは、窒素原子、1,3,5−ベンゼントリイル基又は2,4,6−トリアジントリイル基を表す。1,3,5−ベンゼントリイル基は2,4,6−位に置換基を有していてもよく、置換基としては、例えば、アルキル基、芳香族炭化水素環基、ハロゲン原子などが挙げられる。
また、本発明における電子注入層は、前述の還元性ドーパントを含有していても好ましい。
本発明の有機EL素子の各有機層の膜厚は特に制限されないが、一般に膜厚が薄すぎるとピンホール等の欠陥が生じやすく、逆に厚すぎると高い印加電圧が必要となり効率が悪くなるため、通常は数nmから1μmの範囲が好ましい。
化合物No.6の合成
反応終了後、室温まで冷却した。試料を分液ロートに移し、水50mlを加え、CH2Cl2にて抽出した。MgSO4で乾燥後、ろ過、濃縮した。試料をトルエン300mlに溶解し、カラムクロマトグラフィーで精製後、濃縮・乾固し、酢酸エチル(30ml)で洗浄を3回行い、白色の粉末(No.6)を得た。これを昇華精製し、白色の固体を得た。収量3.5g。
FDマススペクトル分析
C36H23NO:理論値485,観測値485
化合物No.1の合成
反応終了後、室温まで冷却した。試料をメタノール100mlに注ぎ込み、析出した固体を吸引ろ過で回収した。試料をカラムクロマトグラフィーで精製した。濃縮・乾固の後、再結晶を2回行い白色の粉末(No.1)を得た。これを昇華精製して白色の固体を得た。収量2.6g。
FDマススペクトル分析
C42H27NO:理論値561,観測値561
化合物No.12の合成
反応終了後、室温まで冷却した。試料を分液ロートに移し、水50mlを加え、CH2Cl2にて抽出した。試料をカラムクロマトグラフィーで精製した。濃縮・乾固の後、再結晶を2回行い白色の粉末(No.12)を得た。これを昇華精製して白色の固体を得た。収量3.2g。
FDマススペクトル分析
C42H25NO2:理論値575,観測値575
化合物No.18の合成
反応終了後、室温まで冷却した。試料を分液ロートに移し、水50mlを加え、CH2Cl2にて抽出した。試料をカラムクロマトグラフィーで精製した。濃縮・乾固の後、再結晶を2回行い白色の粉末(No.18)を得た。これを昇華精製して白色の固体を得た。収量3.2g。
FDマススペクトル分析
C48H29NO2:理論値651,観測値651
化合物No.72の合成
反応終了後、室温まで冷却した。試料を分液ロートに移し、水50mlを加え、CH2Cl2にて抽出した。試料をカラムクロマトグラフィーで精製した。濃縮・乾固の後、再結晶を2回行い白色の粉末(No.72)を得た。これを昇華精製して白色の固体を得た。収量2.8g。
FDマススペクトル分析
C39H26S2:理論値558,観測値558
化合物No.66の合成
反応終了後、室温まで冷却した。試料を分液ロートに移し、水70mlを加え、CH2Cl2にて抽出した。試料をカラムクロマトグラフィーで精製した。濃縮・乾固の後、再結晶を3回行い白色の粉末(No.66)を得た。これを昇華精製して白色の固体を得た。収量4.0g。
FDマススペクトル分析
C46H28N4O:理論値652,観測値652
化合物No.5の合成
反応終了後、室温まで冷却した。試料を分液ロートに移し、水50mlを加え、CH2Cl2にて抽出した。試料をカラムクロマトグラフィーで精製した。濃縮・乾固の後、再結晶を3回行い白色の粉末(No.5)を得た。これを昇華精製して白色の固体を得た。収量2.2g。
FDマススペクトル分析
C60H36N2O2:理論値816,観測値816
合成実施例1〜7においてFD−MS(フィールドディソープションマス分析)の測定に用いた装置及び測定条件を以下に示す。
装置:HX110(日本電子社製)
条件:加速電圧 8kV
スキャンレンジ m/z=50〜1500
エミッタ種:カーボン
エミッタ電流:0mA→2mA/分→40mA(10分保持)
(有機EL素子の作製)
25mm×75mm×1.1mm厚のITO透明電極付きガラス基板(旭硝子製)をイソプロピルアルコール中で5分間超音波洗浄した後、30分間UVオゾン洗浄した。洗浄後の透明電極ライン付きガラス基板を真空蒸着装置の基板ホルダーに装着し、まず透明電極ラインが形成されている側の面上に、前記透明電極を覆うようにして膜厚80nmのHTM1(下記構造式参照)膜を抵抗加熱により成膜した。該HTM1膜は正孔輸送/正孔注入層として機能する。引き続いて、該HTM1膜上に、ホスト化合物として化合物No.5およびドーパント化合物として錯体K−21を含む膜厚30nmの共蒸着膜を抵抗加熱により成膜した。錯体K−21の濃度は7.5wt%であった。この共蒸着膜は発光層として機能する。引き続き、該発光層上に膜厚10nmのETM1膜、該ETM1膜上に膜厚20nmのETM2膜を積層成膜した。該ETM1膜及びETM2膜はそれぞれ第一及び第二電子輸送層として機能する。次いで、成膜速度0.1Å/minで膜厚0.5nmのLiF電子注入性電極(陰極)を形成した。このLiF層上に金属Alを蒸着させ、膜厚150nmの金属陰極を形成し有機EL素子を得た。
以上のように作製した有機EL素子を直流電流駆動により発光させ、発光波長(λ)、輝度(L)、電流密度を測定し、電流効率(L/J)を求めた。結果を表1に示す。
実施例1においてホスト化合物No.5を用いる代わりに表1に記載のホスト材料を用いた以外は実施例1と同様にして有機EL素子を作製した。発光性能評価結果を表1に示す。
実施例1においてホスト化合物No.5を用いる代わりにホスト材料としてCBPを用いた以外は実施例1と同様にして有機EL素子を作製した。発光性能評価結果を表1に示す。
実施例1においてホスト化合物No.5を用いる代わりにホスト材料として国際公開特許WO2005−113531号公報記載の下記化合物X−1を用いた以外は実施例1と同様にして有機EL素子を作製した。発光性能評価結果を表1に示す。
実施例1において正孔輸送/正孔注入層としてHTM1を用いる代わりに表2に記載の本発明化合物を用い、ホスト材料として下記H−1を用いた以外は実施例1と同様にして有機EL素子を作製した。発光性能評価結果を表2に示す。
Claims (19)
- 下記一般式(1)で表される化合物からなる、少なくとも1種のりん光発光性の金属錯体とともに用いる有機エレクトロルミネッセンス素子用材料。
R6とR10は、それぞれ独立に、水素原子または置換基を有してもよい炭素数1〜40のアルキル基であり、
R7〜R9は、それぞれ独立に、水素原子、ハロゲン原子、置換基を有してもよい炭素数1〜40のアルキル基、置換基を有してもよい炭素数3〜15のシクロアルキル基、置換基を有してもよい炭素数3〜20の複素環基、置換基を有してもよい炭素数1〜40のアルコキシ基、置換基を有してもよい炭素数6〜40の非縮合アリール基、置換基を有してもよい炭素数10〜18の縮合アリール基、置換基を有してもよい炭素数6〜20のアリールオキシ基、置換基を有してもよい炭素数7〜20のアラルキル基、置換基を有してもよい炭素数6〜40のアリールアミノ基、置換基を有してもよい炭素数1〜40のアルキルアミノ基、置換基を有してもよい炭素数7〜60のアラルキルアミノ基、置換基を有してもよい炭素数7〜40のアリールカルボニル基、置換基を有してもよい炭素数6〜20のアリールチオ基、置換基を有してもよい炭素数1〜40のハロゲン化アルキル基、または、シアノ基である、但し、R8とR9またはR8とR7が互いに結合して環構造を形成しない場合、R7〜R9の少なくとも1つは置換基を有してもよい9−カルバゾリル基、置換基を有してもよい窒素原子数2〜5のアザカルバゾリル基、置換基を有してもよいジベンゾフラニル基、置換基を有してもよいジベンゾチオフェニル基、または、置換基を有してもよいフェニル基またはビフェニル基であり、該フェニル基またはビフェニル基は、置換基を有してもよい9−カルバゾリル基、置換基を有してもよい窒素原子数2〜5のアザカルバゾリル基、置換基を有してもよいジベンゾフラニル基、および、置換基を有してもよいジベンゾチオフェニル基から選ばれる少なくとも1つの基で置換されており、
R8とR9またはR8とR7は互いに結合して置換基を有してもよい環構造を形成してもよく、該環構造を形成しないR7またはR9は水素原子、ハロゲン原子、置換基を有してもよい炭素数1〜40のアルキル基、置換基を有してもよい炭素数3〜15のシクロアルキル基、置換基を有してもよい炭素数3〜20の複素環基、置換基を有してもよい炭素数1〜40のアルコキシ基、置換基を有してもよい炭素数6〜40の非縮合アリール基、置換基を有してもよい炭素数10〜18の縮合アリール基、置換基を有してもよい炭素数6〜20のアリールオキシ基、置換基を有してもよい炭素数7〜20のアラルキル基、置換基を有してもよい炭素数6〜40のアリールアミノ基、置換基を有してもよい炭素数1〜40のアルキルアミノ基、置換基を有してもよい炭素数7〜60のアラルキルアミノ基、置換基を有してもよい炭素数7〜40のアリールカルボニル基、置換基を有してもよい炭素数6〜20のアリールチオ基、置換基を有してもよい炭素数1〜40のハロゲン化アルキル基、または、シアノ基である、但し、R8とR9またはR8とR7とそれらが結合しているベンゼン環がカルバゾリル基を形成する場合は除く、
R7〜R9のいずれかが置換基を有してもよいジベンゾフラニル基または置換基を有してもよいジベンゾチオフェニル基である場合、R1〜R3のすべては水素原子であり、
R1〜R3およびR6〜R10の各置換基は末端に重合性官能基を有することはなく、
Xは、硫黄原子または酸素原子である]。 - 前記一般式(2)の置換基R7、R8およびR20〜R24の少なくとも1つ、前記一般式(3)の置換基R7、R9およびR20〜R24の少なくとも1つ、前記一般式(4)の置換基R7およびR21〜R23の少なくとも1つ、前記一般式(5)の置換基R7、R8、R20、およびR22〜R29の少なくとも1つ、前記一般式(6)の置換基R7、R8およびR20〜R24の少なくとも1つ、前記一般式(7)の置換基R7、R9およびR20〜R24の少なくとも1つ、前記一般式(8)の置換基R22およびR23の少なくとも1つ、および、前記一般式(9)の置換基R7、R21およびR23の少なくとも1つは、置換又は無置換の9−カルバゾリル基、置換又は無置換のジベンゾフラニル基、置換又は無置換の窒素原子数2〜5のアザカルバゾリル基、および置換又は無置換のジベンゾチオフェニル基から選ばれた置換基である請求項2〜9のいずれか一項に記載の有機エレクトロルミネッセンス素子用材料。
- 前記一般式(1)〜(9)のいずれかで表される化合物の3重項エネルギーギャップが2.2〜3.2eVである請求項1〜10のいずれかに一項記載の有機エレクトロルミネッセンス素子用材料。
- 陰極と陽極間に一層又は複数層からなる有機薄膜層が挟持されており、該有機薄膜層の少なくとも1層が少なくとも1種のりん光発光性の金属錯体とともに用いるホスト材料を含有する発光層であり、該有機薄膜層の少なくとも一層が請求項1〜11のいずれかに一項記載の有機エレクトロルミネッセンス素子用材料を含有する有機エレクトロルミネッセンス素子。
- 前記発光層が含有するホスト材料が前記有機エレクトロルミネッセンス素子用材料である請求項12記載の有機エレクトロルミネッセンス素子。
- 前記発光層がホスト材料とりん光性の発光材料を含有す請求項13記載の有機エレクトロルミネッセンス素子。
- 前記りん光性の発光材料がイリジウム(Ir)、オスミウム(Os)又は白金(Pt)金属を含有する化合物である請求項14記載の有機エレクトロルミネッセンス素子。
- 前記発光層の発光波長の最大ピーク波長が500nm以下である青色系金属錯体を含有する請求項14記載の有機エレクトロルミネッセンス素子。
- 前記有機薄膜層の少なくとも1層が電子注入層であり、該電子注入層が、前記有機エレクトロルミネッセンス素子用材料とは異なる含窒素環誘導体を主成分として含有する請求項12記載の有機エレクトロルミネッセンス素子。
- 前記有機薄膜層の少なくとも1層が正孔輸送層であり、該正孔輸送層が前記有機エレクトロルミネッセンス素子用材料を含有する請求項12記載の有機エレクトロルミネッセンス素子。
- 陰極と有機薄膜層との界面領域に還元性ドーパントが添加されてなる請求項12記載の有機エレクトロルミネッセンス素子。
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Families Citing this family (640)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9070884B2 (en) | 2005-04-13 | 2015-06-30 | Universal Display Corporation | Hybrid OLED having phosphorescent and fluorescent emitters |
US9051344B2 (en) | 2005-05-06 | 2015-06-09 | Universal Display Corporation | Stability OLED materials and devices |
US8586204B2 (en) | 2007-12-28 | 2013-11-19 | Universal Display Corporation | Phosphorescent emitters and host materials with improved stability |
CN101184822B (zh) * | 2005-05-30 | 2014-11-26 | 西巴特殊化学品控股有限公司 | 电致发光器件 |
US7915415B2 (en) | 2006-02-10 | 2011-03-29 | Universal Display Corporation | Metal complexes of cyclometallated imidazo[1,2-f]phenanthridine and diimidazo[1,2-a:1′,2′-c]quinazoline ligands and isoelectronic and benzannulated analogs thereof |
US8778508B2 (en) | 2006-12-08 | 2014-07-15 | Universal Display Corporation | Light-emitting organometallic complexes |
US8541112B2 (en) | 2006-12-13 | 2013-09-24 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, display device and lighting device |
KR101634392B1 (ko) | 2007-03-08 | 2016-06-28 | 유니버셜 디스플레이 코포레이션 | 인광성 물질 |
US20130032785A1 (en) | 2011-08-01 | 2013-02-07 | Universal Display Corporation | Materials for organic light emitting diode |
US9130177B2 (en) | 2011-01-13 | 2015-09-08 | Universal Display Corporation | 5-substituted 2 phenylquinoline complexes materials for light emitting diode |
WO2009021107A1 (en) | 2007-08-08 | 2009-02-12 | Universal Display Corporation | Single triphenylene chromophores in phosphorescent light emitting diodes |
US8080658B2 (en) * | 2007-07-10 | 2011-12-20 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescent element and organic electroluminescent element employing the same |
KR101453128B1 (ko) | 2007-07-10 | 2014-10-27 | 이데미쓰 고산 가부시키가이샤 | 유기 전기발광 소자용 재료 및 그것을 이용한 유기 전기발광 소자 |
US8111001B2 (en) | 2007-07-17 | 2012-02-07 | Cree, Inc. | LED with integrated constant current driver |
TWI551594B (zh) | 2007-08-08 | 2016-10-01 | 環球展覽公司 | 有機電發光材料及裝置 |
KR101507783B1 (ko) * | 2007-10-01 | 2015-04-03 | 엘지전자 주식회사 | 가전장치 및 이의 제어방법 |
WO2009085344A2 (en) | 2007-12-28 | 2009-07-09 | Universal Display Corporation | Dibenzothiophene-containing materials in phosphorescent light emitting diodes |
WO2009145016A1 (ja) | 2008-05-29 | 2009-12-03 | 出光興産株式会社 | 芳香族アミン誘導体及びそれらを用いた有機エレクトロルミネッセンス素子 |
KR20100000772A (ko) * | 2008-06-25 | 2010-01-06 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 발광 소자 |
KR101778910B1 (ko) | 2008-06-30 | 2017-09-14 | 유니버셜 디스플레이 코포레이션 | 트리페닐렌을 포함하는 정공 수송 물질 |
WO2010027583A1 (en) | 2008-09-03 | 2010-03-11 | Universal Display Corporation | Phosphorescent materials |
TWI555734B (zh) | 2008-09-16 | 2016-11-01 | 環球展覽公司 | 磷光物質 |
US8426035B2 (en) | 2008-09-25 | 2013-04-23 | Universal Display Corporation | Organoselenium materials and their uses in organic light emitting devices |
US8367223B2 (en) * | 2008-11-11 | 2013-02-05 | Universal Display Corporation | Heteroleptic phosphorescent emitters |
KR101571986B1 (ko) * | 2008-11-25 | 2015-11-25 | 이데미쓰 고산 가부시키가이샤 | 방향족 아민 유도체 및 유기 전기발광 소자 |
US8815415B2 (en) | 2008-12-12 | 2014-08-26 | Universal Display Corporation | Blue emitter with high efficiency based on imidazo[1,2-f] phenanthridine iridium complexes |
US9067947B2 (en) | 2009-01-16 | 2015-06-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
WO2010090077A1 (ja) * | 2009-02-06 | 2010-08-12 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、該素子を備えた照明装置及び表示装置 |
EP2399906A4 (en) * | 2009-02-18 | 2012-08-29 | Idemitsu Kosan Co | AROMATIC AMINE DERIVATIVE AND ORGANIC ELECTROLUMINESCENT ELEMENT |
US8709615B2 (en) | 2011-07-28 | 2014-04-29 | Universal Display Corporation | Heteroleptic iridium complexes as dopants |
US11910700B2 (en) | 2009-03-23 | 2024-02-20 | Universal Display Corporation | Heteroleptic iridium complexes as dopants |
US8722205B2 (en) | 2009-03-23 | 2014-05-13 | Universal Display Corporation | Heteroleptic iridium complex |
US20120074395A1 (en) * | 2009-04-01 | 2012-03-29 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent element |
US8557400B2 (en) | 2009-04-28 | 2013-10-15 | Universal Display Corporation | Iridium complex with methyl-D3 substitution |
US8586203B2 (en) | 2009-05-20 | 2013-11-19 | Universal Display Corporation | Metal complexes with boron-nitrogen heterocycle containing ligands |
JP5321684B2 (ja) | 2009-06-24 | 2013-10-23 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、表示装置、照明装置及び縮合多環式複素環化合物 |
KR101097313B1 (ko) * | 2009-08-10 | 2011-12-23 | 삼성모바일디스플레이주식회사 | 유기 발광 소자 |
KR101108154B1 (ko) | 2009-08-10 | 2012-02-08 | 삼성모바일디스플레이주식회사 | 축합환 화합물 및 이를 포함한 유기층을 구비한 유기 발광 소자 |
JP5742092B2 (ja) * | 2009-09-02 | 2015-07-01 | 三菱化学株式会社 | 有機化合物、電荷輸送材料、有機電界発光素子用組成物、有機電界発光素子、有機elディスプレイ及び有機el照明 |
WO2011051404A1 (de) | 2009-10-28 | 2011-05-05 | Basf Se | Heteroleptische carben-komplexe und deren verwendung in der organischen elektronik |
US8545996B2 (en) | 2009-11-02 | 2013-10-01 | The University Of Southern California | Ion-pairing soft salts based on organometallic complexes and their applications in organic light emitting diodes |
JP5739815B2 (ja) * | 2009-11-16 | 2015-06-24 | 出光興産株式会社 | 芳香族アミン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
US8580394B2 (en) | 2009-11-19 | 2013-11-12 | Universal Display Corporation | 3-coordinate copper(I)-carbene complexes |
KR101838199B1 (ko) | 2009-12-14 | 2018-04-26 | 유디씨 아일랜드 리미티드 | 디아자벤즈이미다졸로카르벤 리간드를 포함하는 금속 착물 및 oled에서의 그의 용도 |
US8288187B2 (en) | 2010-01-20 | 2012-10-16 | Universal Display Corporation | Electroluminescent devices for lighting applications |
JP5620125B2 (ja) * | 2010-01-28 | 2014-11-05 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子 |
US9156870B2 (en) * | 2010-02-25 | 2015-10-13 | Universal Display Corporation | Phosphorescent emitters |
US9175211B2 (en) * | 2010-03-03 | 2015-11-03 | Universal Display Corporation | Phosphorescent materials |
WO2011119162A1 (en) | 2010-03-25 | 2011-09-29 | Universal Display Corporation | Solution processable doped triarylamine hole injection materials |
CN102823015B (zh) * | 2010-03-31 | 2014-05-14 | 出光兴产株式会社 | 有机电致发光元件用材料和使用其的有机电致发光元件 |
US8691401B2 (en) | 2010-04-16 | 2014-04-08 | Basf Se | Bridged benzimidazole-carbene complexes and use thereof in OLEDS |
US8968887B2 (en) | 2010-04-28 | 2015-03-03 | Universal Display Corporation | Triphenylene-benzofuran/benzothiophene/benzoselenophene compounds with substituents joining to form fused rings |
CN103026521B (zh) | 2010-04-28 | 2016-11-09 | 通用显示公司 | 沉积预混合的材料 |
US8673458B2 (en) | 2010-06-11 | 2014-03-18 | Universal Display Corporation | Delayed fluorescence OLED |
US8742657B2 (en) | 2010-06-11 | 2014-06-03 | Universal Display Corporation | Triplet-Triplet annihilation up conversion (TTA-UC) for display and lighting applications |
US9142792B2 (en) | 2010-06-18 | 2015-09-22 | Basf Se | Organic electronic devices comprising a layer comprising at least one metal organic compound and at least one metal oxide |
US9435021B2 (en) | 2010-07-29 | 2016-09-06 | University Of Southern California | Co-deposition methods for the fabrication of organic optoelectronic devices |
JP5770289B2 (ja) | 2010-08-20 | 2015-08-26 | ユニバーサル ディスプレイ コーポレイション | Oledのためのビカルバゾール化合物 |
EP2617712A4 (en) * | 2010-08-31 | 2014-02-19 | Idemitsu Kosan Co | NITROGEN-CONTAINING AROMATIC HETEROCYCLIC DERIVATIVE AND ORGANIC ELECTROLUMINESCENZING DEVICE THEREWITH |
JP5847420B2 (ja) | 2010-09-08 | 2016-01-20 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子及び化合物 |
JP5815341B2 (ja) * | 2010-09-09 | 2015-11-17 | 株式会社半導体エネルギー研究所 | 複素環化合物 |
US8932734B2 (en) | 2010-10-08 | 2015-01-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR101213498B1 (ko) | 2010-10-25 | 2012-12-20 | 삼성디스플레이 주식회사 | 유기 전계 발광 장치 |
US8269317B2 (en) | 2010-11-11 | 2012-09-18 | Universal Display Corporation | Phosphorescent materials |
US20120138906A1 (en) | 2010-12-07 | 2012-06-07 | The University of Southern California USC Stevens Institute for Innovation | Capture agents for unsaturated metal complexes |
US9705091B2 (en) | 2010-12-20 | 2017-07-11 | Idemitsu Kosan Co., Ltd. | Aromatic heterocycle derivative and organic electroluminescent element using same |
KR101867115B1 (ko) * | 2010-12-28 | 2018-07-19 | 이데미쓰 고산 가부시키가이샤 | 유기 전기발광 소자용 재료 및 그것을 이용한 유기 전기발광 소자 |
US10008677B2 (en) | 2011-01-13 | 2018-06-26 | Universal Display Corporation | Materials for organic light emitting diode |
KR101831015B1 (ko) | 2011-01-20 | 2018-02-21 | 이데미쓰 고산 가부시키가이샤 | 유기 일렉트로 루미네선스 소자 |
US8415031B2 (en) | 2011-01-24 | 2013-04-09 | Universal Display Corporation | Electron transporting compounds |
KR101874657B1 (ko) | 2011-02-07 | 2018-07-04 | 이데미쓰 고산 가부시키가이샤 | 비스카바졸 유도체 및 그것을 이용한 유기 전기발광 소자 |
JP5745549B2 (ja) | 2011-02-07 | 2015-07-08 | 出光興産株式会社 | ビスカルバゾール誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
US8748011B2 (en) | 2011-02-23 | 2014-06-10 | Universal Display Corporation | Ruthenium carbene complexes for OLED material |
CN106749425B (zh) | 2011-02-23 | 2020-07-14 | 通用显示公司 | 新型的四齿铂络合物 |
US9005772B2 (en) | 2011-02-23 | 2015-04-14 | Universal Display Corporation | Thioazole and oxazole carbene metal complexes as phosphorescent OLED materials |
US8563737B2 (en) | 2011-02-23 | 2013-10-22 | Universal Display Corporation | Methods of making bis-tridentate carbene complexes of ruthenium and osmium |
US8492006B2 (en) | 2011-02-24 | 2013-07-23 | Universal Display Corporation | Germanium-containing red emitter materials for organic light emitting diode |
JP5330429B2 (ja) * | 2011-03-08 | 2013-10-30 | 株式会社東芝 | 有機電界発光素子、表示装置および照明装置 |
US8883322B2 (en) | 2011-03-08 | 2014-11-11 | Universal Display Corporation | Pyridyl carbene phosphorescent emitters |
US8580399B2 (en) * | 2011-04-08 | 2013-11-12 | Universal Display Corporation | Substituted oligoazacarbazoles for light emitting diodes |
US8432095B2 (en) | 2011-05-11 | 2013-04-30 | Universal Display Corporation | Process for fabricating metal bus lines for OLED lighting panels |
US8927308B2 (en) | 2011-05-12 | 2015-01-06 | Universal Display Corporation | Method of forming bus line designs for large-area OLED lighting |
WO2012153780A1 (ja) | 2011-05-11 | 2012-11-15 | 出光興産株式会社 | 新規化合物、有機エレクトロルミネッセンス素子用材料及び有機エレクトロルミネッセンス素子 |
US8564192B2 (en) | 2011-05-11 | 2013-10-22 | Universal Display Corporation | Process for fabricating OLED lighting panels |
US9212197B2 (en) | 2011-05-19 | 2015-12-15 | Universal Display Corporation | Phosphorescent heteroleptic phenylbenzimidazole dopants |
US8795850B2 (en) | 2011-05-19 | 2014-08-05 | Universal Display Corporation | Phosphorescent heteroleptic phenylbenzimidazole dopants and new synthetic methodology |
US8748012B2 (en) | 2011-05-25 | 2014-06-10 | Universal Display Corporation | Host materials for OLED |
US10158089B2 (en) | 2011-05-27 | 2018-12-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10079349B2 (en) | 2011-05-27 | 2018-09-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR20140041551A (ko) | 2011-06-08 | 2014-04-04 | 유니버셜 디스플레이 코포레이션 | 헤테로렙틱 이리듐 카르벤 착물 및 이를 사용한 발광 디바이스 |
KR101950460B1 (ko) | 2011-06-14 | 2019-02-20 | 유디씨 아일랜드 리미티드 | 아자벤즈이미다졸 카르벤 리간드를 포함하는 금속 착물 및 oled 에서의 이의 용도 |
US9315724B2 (en) | 2011-06-14 | 2016-04-19 | Basf Se | Metal complexes comprising azabenzimidazole carbene ligands and the use thereof in OLEDs |
US8884316B2 (en) | 2011-06-17 | 2014-11-11 | Universal Display Corporation | Non-common capping layer on an organic device |
US8659036B2 (en) | 2011-06-17 | 2014-02-25 | Universal Display Corporation | Fine tuning of emission spectra by combination of multiple emitter spectra |
US9023420B2 (en) | 2011-07-14 | 2015-05-05 | Universal Display Corporation | Composite organic/inorganic layer for organic light-emitting devices |
US9397310B2 (en) | 2011-07-14 | 2016-07-19 | Universal Display Corporation | Organice electroluminescent materials and devices |
US9252377B2 (en) | 2011-07-14 | 2016-02-02 | Universal Display Corporation | Inorganic hosts in OLEDs |
US9783564B2 (en) | 2011-07-25 | 2017-10-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US8409729B2 (en) | 2011-07-28 | 2013-04-02 | Universal Display Corporation | Host materials for phosphorescent OLEDs |
US8926119B2 (en) | 2011-08-04 | 2015-01-06 | Universal Display Corporation | Extendable light source with variable light emitting area |
US8552420B2 (en) | 2011-08-09 | 2013-10-08 | Universal Display Corporation | OLED light panel with controlled brightness variation |
US9493698B2 (en) | 2011-08-31 | 2016-11-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR102048688B1 (ko) | 2011-09-09 | 2019-11-26 | 이데미쓰 고산 가부시키가이샤 | 질소 함유 헤테로 방향족환 화합물 |
CN103797604B (zh) * | 2011-09-09 | 2017-02-15 | 株式会社Lg化学 | 用于有机发光器件的材料以及使用其的有机发光器件 |
KR101992874B1 (ko) | 2011-09-12 | 2019-06-26 | 닛테츠 케미컬 앤드 머티리얼 가부시키가이샤 | 유기 전계 발광 소자 |
EP2757607B1 (en) * | 2011-09-12 | 2016-02-10 | Nippon Steel & Sumikin Chemical Co., Ltd. | Organic electroluminescent element |
US8652656B2 (en) | 2011-11-14 | 2014-02-18 | Universal Display Corporation | Triphenylene silane hosts |
US9193745B2 (en) | 2011-11-15 | 2015-11-24 | Universal Display Corporation | Heteroleptic iridium complex |
US9217004B2 (en) | 2011-11-21 | 2015-12-22 | Universal Display Corporation | Organic light emitting materials |
KR102261235B1 (ko) | 2011-11-22 | 2021-06-04 | 이데미쓰 고산 가부시키가이샤 | 방향족 복소 고리 유도체, 유기 일렉트로루미네선스 소자용 재료 및 유기 일렉트로루미네선스 소자 |
US9512355B2 (en) | 2011-12-09 | 2016-12-06 | Universal Display Corporation | Organic light emitting materials |
US20130146875A1 (en) | 2011-12-13 | 2013-06-13 | Universal Display Corporation | Split electrode for organic devices |
JP5857724B2 (ja) * | 2011-12-20 | 2016-02-10 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、表示装置、照明装置及び有機エレクトロルミネッセンス素子の製造方法 |
US9461254B2 (en) | 2012-01-03 | 2016-10-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
US8987451B2 (en) | 2012-01-03 | 2015-03-24 | Universal Display Corporation | Synthesis of cyclometallated platinum(II) complexes |
US9163174B2 (en) | 2012-01-04 | 2015-10-20 | Universal Display Corporation | Highly efficient phosphorescent materials |
KR102012047B1 (ko) | 2012-01-06 | 2019-08-19 | 유니버셜 디스플레이 코포레이션 | 효율이 큰 인광 물질 |
US8969592B2 (en) | 2012-01-10 | 2015-03-03 | Universal Display Corporation | Heterocyclic host materials |
US10211413B2 (en) | 2012-01-17 | 2019-02-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9118017B2 (en) | 2012-02-27 | 2015-08-25 | Universal Display Corporation | Host compounds for red phosphorescent OLEDs |
US9054323B2 (en) | 2012-03-15 | 2015-06-09 | Universal Display Corporation | Secondary hole transporting layer with diarylamino-phenyl-carbazole compounds |
US9386657B2 (en) | 2012-03-15 | 2016-07-05 | Universal Display Corporation | Organic Electroluminescent materials and devices |
US8723209B2 (en) | 2012-04-27 | 2014-05-13 | Universal Display Corporation | Out coupling layer containing particle polymer composite |
US9184399B2 (en) | 2012-05-04 | 2015-11-10 | Universal Display Corporation | Asymmetric hosts with triaryl silane side chains |
US9773985B2 (en) | 2012-05-21 | 2017-09-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9670404B2 (en) | 2012-06-06 | 2017-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9502672B2 (en) | 2012-06-21 | 2016-11-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9725476B2 (en) | 2012-07-09 | 2017-08-08 | Universal Display Corporation | Silylated metal complexes |
US9231218B2 (en) | 2012-07-10 | 2016-01-05 | Universal Display Corporation | Phosphorescent emitters containing dibenzo[1,4]azaborinine structure |
WO2014010824A1 (ko) * | 2012-07-13 | 2014-01-16 | 주식회사 엘지화학 | 헤테로환 화합물 및 이를 포함하는 유기 전자 소자 |
JP6271538B2 (ja) | 2012-07-19 | 2018-01-31 | ユー・ディー・シー アイルランド リミテッド | カルベン配位子を含む複核金属錯体およびoledにおけるその使用 |
US9540329B2 (en) | 2012-07-19 | 2017-01-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9059412B2 (en) | 2012-07-19 | 2015-06-16 | Universal Display Corporation | Transition metal complexes containing substituted imidazole carbene as ligands and their application in OLEDs |
WO2014013721A1 (ja) * | 2012-07-20 | 2014-01-23 | 出光興産株式会社 | 含窒素ヘテロ芳香族環化合物、それを用いた有機エレクトロルミネッセンス素子 |
US9663544B2 (en) | 2012-07-25 | 2017-05-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9318710B2 (en) | 2012-07-30 | 2016-04-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
WO2014030666A1 (ja) | 2012-08-24 | 2014-02-27 | コニカミノルタ株式会社 | 透明電極、電子デバイス、および透明電極の製造方法 |
US9978958B2 (en) | 2012-08-24 | 2018-05-22 | Universal Display Corporation | Phosphorescent emitters with phenylimidazole ligands |
US8952362B2 (en) | 2012-08-31 | 2015-02-10 | The Regents Of The University Of Michigan | High efficiency and brightness fluorescent organic light emitting diode by triplet-triplet fusion |
EP2891648B1 (en) | 2012-08-31 | 2022-02-16 | Idemitsu Kosan Co., Ltd | Aromatic amine derivative, and organic electroluminescent element using the same |
US10957870B2 (en) | 2012-09-07 | 2021-03-23 | Universal Display Corporation | Organic light emitting device |
US9287513B2 (en) | 2012-09-24 | 2016-03-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9312505B2 (en) | 2012-09-25 | 2016-04-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
JP6194645B2 (ja) * | 2012-09-27 | 2017-09-13 | 東ソー株式会社 | アミン化合物及びその用途 |
US9252363B2 (en) | 2012-10-04 | 2016-02-02 | Universal Display Corporation | Aryloxyalkylcarboxylate solvent compositions for inkjet printing of organic layers |
US8692241B1 (en) | 2012-11-08 | 2014-04-08 | Universal Display Corporation | Transition metal complexes containing triazole and tetrazole carbene ligands |
US9634264B2 (en) | 2012-11-09 | 2017-04-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
US8946697B1 (en) | 2012-11-09 | 2015-02-03 | Universal Display Corporation | Iridium complexes with aza-benzo fused ligands |
US9685617B2 (en) | 2012-11-09 | 2017-06-20 | Universal Display Corporation | Organic electronuminescent materials and devices |
US9748500B2 (en) | 2015-01-15 | 2017-08-29 | Universal Display Corporation | Organic light emitting materials |
US9190623B2 (en) | 2012-11-20 | 2015-11-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10069090B2 (en) | 2012-11-20 | 2018-09-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9512136B2 (en) | 2012-11-26 | 2016-12-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9166175B2 (en) | 2012-11-27 | 2015-10-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9196860B2 (en) | 2012-12-04 | 2015-11-24 | Universal Display Corporation | Compounds for triplet-triplet annihilation upconversion |
US8716484B1 (en) | 2012-12-05 | 2014-05-06 | Universal Display Corporation | Hole transporting materials with twisted aryl groups |
US9209411B2 (en) | 2012-12-07 | 2015-12-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR20170127065A (ko) | 2012-12-10 | 2017-11-20 | 코니카 미놀타 가부시키가이샤 | 유기 일렉트로루미네센스 소자 재료, 유기 일렉트로루미네센스 소자, 조명 장치 및 표시 장치 |
EP2930763B1 (en) * | 2012-12-10 | 2020-07-29 | Konica Minolta, Inc. | Organic electroluminescence element, illumination device and display device |
US9653691B2 (en) | 2012-12-12 | 2017-05-16 | Universal Display Corporation | Phosphorescence-sensitizing fluorescence material system |
KR20140080606A (ko) | 2012-12-12 | 2014-07-01 | 삼성전자주식회사 | 유기 금속 착물, 이를 이용한 유기 전계 발광 소자 및 표시 장치 |
WO2014112359A1 (ja) * | 2013-01-15 | 2014-07-24 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子 |
US10400163B2 (en) | 2013-02-08 | 2019-09-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10367154B2 (en) | 2013-02-21 | 2019-07-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
US8927749B2 (en) | 2013-03-07 | 2015-01-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9419225B2 (en) | 2013-03-14 | 2016-08-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
TWI734860B (zh) | 2013-03-20 | 2021-08-01 | 愛爾蘭商Udc愛爾蘭責任有限公司 | 包含Ir金屬-碳烯錯合物之有機電子裝置及設備 |
US9997712B2 (en) | 2013-03-27 | 2018-06-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR101798307B1 (ko) | 2013-03-29 | 2017-11-15 | 코니카 미놀타 가부시키가이샤 | 유기 일렉트로루미네센스 소자용 재료, 유기 일렉트로루미네센스 소자, 표시 장치 및 조명 장치 |
JP6314599B2 (ja) | 2013-03-29 | 2018-04-25 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス用化合物、有機エレクトロルミネッセンス素子、それを具備した照明装置及び表示装置 |
EP2991997B1 (en) | 2013-04-29 | 2018-02-21 | UDC Ireland Limited | Transition metal complexes with carbene ligands and the use thereof in oleds |
US9537106B2 (en) | 2013-05-09 | 2017-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9735373B2 (en) | 2013-06-10 | 2017-08-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9673401B2 (en) | 2013-06-28 | 2017-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10199581B2 (en) | 2013-07-01 | 2019-02-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN109438518B (zh) | 2013-07-02 | 2021-06-15 | Udc 爱尔兰有限责任公司 | 用于有机发光二级管中的单取代的二氮杂苯并咪唑卡宾金属络合物 |
US10121975B2 (en) | 2013-07-03 | 2018-11-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9761807B2 (en) | 2013-07-15 | 2017-09-12 | Universal Display Corporation | Organic light emitting diode materials |
US9324949B2 (en) | 2013-07-16 | 2016-04-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9553274B2 (en) | 2013-07-16 | 2017-01-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9224958B2 (en) | 2013-07-19 | 2015-12-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20150028290A1 (en) | 2013-07-25 | 2015-01-29 | Universal Display Corporation | Heteroleptic osmium complex and method of making the same |
EP3027629B1 (en) | 2013-07-31 | 2017-06-14 | UDC Ireland Limited | Luminescent diazabenzimidazole carbene metal complexes |
KR102231935B1 (ko) | 2013-08-05 | 2021-03-25 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물을 이용한 유기전기소자 및 그 전자 장치 |
WO2015020348A1 (ko) * | 2013-08-05 | 2015-02-12 | 덕산하이메탈(주) | 유기전기 소자용 화합물을 이용한 유기전기소자 및 그 전자 장치 |
US10074806B2 (en) | 2013-08-20 | 2018-09-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9831437B2 (en) | 2013-08-20 | 2017-11-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9932359B2 (en) | 2013-08-30 | 2018-04-03 | University Of Southern California | Organic electroluminescent materials and devices |
US10199582B2 (en) | 2013-09-03 | 2019-02-05 | University Of Southern California | Organic electroluminescent materials and devices |
US9735378B2 (en) | 2013-09-09 | 2017-08-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9748503B2 (en) | 2013-09-13 | 2017-08-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
JP6119521B2 (ja) * | 2013-09-19 | 2017-04-26 | コニカミノルタ株式会社 | 透明電極、電子デバイス及び有機エレクトロルミネッセンス素子 |
US10003034B2 (en) | 2013-09-30 | 2018-06-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9831447B2 (en) | 2013-10-08 | 2017-11-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9293712B2 (en) | 2013-10-11 | 2016-03-22 | Universal Display Corporation | Disubstituted pyrene compounds with amino group containing ortho aryl group and devices containing the same |
US9853229B2 (en) | 2013-10-23 | 2017-12-26 | University Of Southern California | Organic electroluminescent materials and devices |
US20150115250A1 (en) | 2013-10-29 | 2015-04-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9306179B2 (en) | 2013-11-08 | 2016-04-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9647218B2 (en) | 2013-11-14 | 2017-05-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10033000B2 (en) | 2013-11-15 | 2018-07-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10056565B2 (en) | 2013-11-20 | 2018-08-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10644251B2 (en) | 2013-12-04 | 2020-05-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9876173B2 (en) | 2013-12-09 | 2018-01-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10355227B2 (en) | 2013-12-16 | 2019-07-16 | Universal Display Corporation | Metal complex for phosphorescent OLED |
US10985329B2 (en) | 2013-12-17 | 2021-04-20 | Samsung Electronics Co., Ltd. | Condensed cyclic compound and organic light-emitting device including the same |
KR102140018B1 (ko) | 2013-12-17 | 2020-07-31 | 삼성전자주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
EP3084855B1 (en) | 2013-12-20 | 2021-08-18 | UDC Ireland Limited | Highly efficient oled devices with very short decay times |
US9847496B2 (en) | 2013-12-23 | 2017-12-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10135008B2 (en) | 2014-01-07 | 2018-11-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9978961B2 (en) | 2014-01-08 | 2018-05-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9755159B2 (en) | 2014-01-23 | 2017-09-05 | Universal Display Corporation | Organic materials for OLEDs |
US9935277B2 (en) | 2014-01-30 | 2018-04-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9590194B2 (en) | 2014-02-14 | 2017-03-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9847497B2 (en) | 2014-02-18 | 2017-12-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10003033B2 (en) | 2014-02-18 | 2018-06-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10707423B2 (en) | 2014-02-21 | 2020-07-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9647217B2 (en) * | 2014-02-24 | 2017-05-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9502656B2 (en) | 2014-02-24 | 2016-11-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10403825B2 (en) | 2014-02-27 | 2019-09-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9181270B2 (en) | 2014-02-28 | 2015-11-10 | Universal Display Corporation | Method of making sulfide compounds |
US9673407B2 (en) | 2014-02-28 | 2017-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9590195B2 (en) | 2014-02-28 | 2017-03-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9190620B2 (en) | 2014-03-01 | 2015-11-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9397309B2 (en) | 2014-03-13 | 2016-07-19 | Universal Display Corporation | Organic electroluminescent devices |
US10208026B2 (en) | 2014-03-18 | 2019-02-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9748504B2 (en) | 2014-03-25 | 2017-08-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR102330660B1 (ko) | 2014-03-31 | 2021-11-24 | 유디씨 아일랜드 리미티드 | o-치환된 비-사이클로메탈화 아릴 그룹을 갖는 카르벤 리간드를 포함하는 금속 착체 및 유기 발광 다이오드에서의 이의 용도 |
GB201405771D0 (en) * | 2014-03-31 | 2014-05-14 | Cambridge Display Tech Ltd | Iodination process, monomer and polymer |
US9929353B2 (en) | 2014-04-02 | 2018-03-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9691993B2 (en) | 2014-04-09 | 2017-06-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9847498B2 (en) | 2014-04-14 | 2017-12-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10008679B2 (en) | 2014-04-14 | 2018-06-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10256427B2 (en) | 2014-04-15 | 2019-04-09 | Universal Display Corporation | Efficient organic electroluminescent devices |
US9450198B2 (en) | 2014-04-15 | 2016-09-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9741941B2 (en) | 2014-04-29 | 2017-08-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10457699B2 (en) | 2014-05-02 | 2019-10-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10403830B2 (en) | 2014-05-08 | 2019-09-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
JP6759108B2 (ja) | 2014-05-08 | 2020-09-23 | ユニバーサル ディスプレイ コーポレイション | 安定化されたイミダゾフェナントリジン材料 |
US10636983B2 (en) | 2014-05-08 | 2020-04-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10301338B2 (en) | 2014-05-08 | 2019-05-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9997716B2 (en) | 2014-05-27 | 2018-06-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10461260B2 (en) | 2014-06-03 | 2019-10-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9911931B2 (en) | 2014-06-26 | 2018-03-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10297762B2 (en) | 2014-07-09 | 2019-05-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10566546B2 (en) | 2014-07-14 | 2020-02-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9929357B2 (en) | 2014-07-22 | 2018-03-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3174885B1 (en) | 2014-07-28 | 2019-10-02 | Idemitsu Kosan Co., Ltd. | 2,9-functionalized benzimidazolo[1,2-a]benzimidazoles as hosts for organic light emitting diodes (oleds) |
US11108000B2 (en) | 2014-08-07 | 2021-08-31 | Unniversal Display Corporation | Organic electroluminescent materials and devices |
US10411200B2 (en) | 2014-08-07 | 2019-09-10 | Universal Display Corporation | Electroluminescent (2-phenylpyridine)iridium complexes and devices |
EP2982676B1 (en) | 2014-08-07 | 2018-04-11 | Idemitsu Kosan Co., Ltd. | Benzimidazo[2,1-B]benzoxazoles for electronic applications |
EP2993215B1 (en) | 2014-09-04 | 2019-06-19 | Idemitsu Kosan Co., Ltd. | Azabenzimidazo[2,1-a]benzimidazoles for electronic applications |
US10749113B2 (en) | 2014-09-29 | 2020-08-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10043987B2 (en) | 2014-09-29 | 2018-08-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10135007B2 (en) | 2014-09-29 | 2018-11-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
JP6516433B2 (ja) * | 2014-10-06 | 2019-05-22 | 三星ディスプレイ株式會社Samsung Display Co.,Ltd. | 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 |
US10361375B2 (en) | 2014-10-06 | 2019-07-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9397302B2 (en) | 2014-10-08 | 2016-07-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10854826B2 (en) | 2014-10-08 | 2020-12-01 | Universal Display Corporation | Organic electroluminescent compounds, compositions and devices |
US10950803B2 (en) | 2014-10-13 | 2021-03-16 | Universal Display Corporation | Compounds and uses in devices |
US9484541B2 (en) | 2014-10-20 | 2016-11-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3015469B1 (en) | 2014-10-30 | 2018-12-19 | Idemitsu Kosan Co., Ltd. | 5-(benzimidazol-2-yl)benzimidazo[1,2-a]benzimidazoles for electronic applications |
US10868261B2 (en) | 2014-11-10 | 2020-12-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10411201B2 (en) | 2014-11-12 | 2019-09-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10038151B2 (en) | 2014-11-12 | 2018-07-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9871212B2 (en) | 2014-11-14 | 2018-01-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9882151B2 (en) | 2014-11-14 | 2018-01-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
WO2016079667A1 (en) | 2014-11-17 | 2016-05-26 | Idemitsu Kosan Co., Ltd. | Indole derivatives for electronic applications |
US9761814B2 (en) | 2014-11-18 | 2017-09-12 | Universal Display Corporation | Organic light-emitting materials and devices |
US10424746B2 (en) | 2014-11-18 | 2019-09-24 | Udc Ireland Limited | Pt- or Pd-carbene complexes for use in organic light emitting diodes |
US9444075B2 (en) | 2014-11-26 | 2016-09-13 | Universal Display Corporation | Emissive display with photo-switchable polarization |
EP3034506A1 (en) | 2014-12-15 | 2016-06-22 | Idemitsu Kosan Co., Ltd | 4-functionalized carbazole derivatives for electronic applications |
EP3034507A1 (en) | 2014-12-15 | 2016-06-22 | Idemitsu Kosan Co., Ltd | 1-functionalized dibenzofurans and dibenzothiophenes for organic light emitting diodes (OLEDs) |
US9450195B2 (en) | 2014-12-17 | 2016-09-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR102307238B1 (ko) * | 2014-12-26 | 2021-10-01 | 솔루스첨단소재 주식회사 | 유기 화합물 및 이를 포함하는 유기 전계 발광 소자 |
US10253252B2 (en) | 2014-12-30 | 2019-04-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10636978B2 (en) | 2014-12-30 | 2020-04-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9312499B1 (en) | 2015-01-05 | 2016-04-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9406892B2 (en) | 2015-01-07 | 2016-08-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10418569B2 (en) | 2015-01-25 | 2019-09-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9711730B2 (en) | 2015-01-25 | 2017-07-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10644247B2 (en) | 2015-02-06 | 2020-05-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3053918B1 (en) | 2015-02-06 | 2018-04-11 | Idemitsu Kosan Co., Ltd. | 2-carbazole substituted benzimidazoles for electronic applications |
US10355222B2 (en) | 2015-02-06 | 2019-07-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10418562B2 (en) | 2015-02-06 | 2019-09-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3054498B1 (en) | 2015-02-06 | 2017-09-20 | Idemitsu Kosan Co., Ltd. | Bisimidazodiazocines |
US10177316B2 (en) | 2015-02-09 | 2019-01-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
JP5831654B1 (ja) | 2015-02-13 | 2015-12-09 | コニカミノルタ株式会社 | 芳香族複素環誘導体、それを用いた有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
US10144867B2 (en) | 2015-02-13 | 2018-12-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10680183B2 (en) | 2015-02-15 | 2020-06-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9929361B2 (en) | 2015-02-16 | 2018-03-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3061759B1 (en) | 2015-02-24 | 2019-12-25 | Idemitsu Kosan Co., Ltd | Nitrile substituted dibenzofurans |
US10600966B2 (en) | 2015-02-27 | 2020-03-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11056657B2 (en) | 2015-02-27 | 2021-07-06 | University Display Corporation | Organic electroluminescent materials and devices |
US10686143B2 (en) | 2015-03-05 | 2020-06-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10270046B2 (en) | 2015-03-06 | 2019-04-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9780316B2 (en) | 2015-03-16 | 2017-10-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3070144B1 (en) | 2015-03-17 | 2018-02-28 | Idemitsu Kosan Co., Ltd. | Seven-membered ring compounds |
US9911928B2 (en) | 2015-03-19 | 2018-03-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9871214B2 (en) | 2015-03-23 | 2018-01-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10529931B2 (en) | 2015-03-24 | 2020-01-07 | Universal Display Corporation | Organic Electroluminescent materials and devices |
EP3072943B1 (en) | 2015-03-26 | 2018-05-02 | Idemitsu Kosan Co., Ltd. | Dibenzofuran/carbazole-substituted benzonitriles |
US10297770B2 (en) | 2015-03-27 | 2019-05-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3075737B1 (en) | 2015-03-31 | 2019-12-04 | Idemitsu Kosan Co., Ltd | Benzimidazolo[1,2-a]benzimidazole carrying aryl- or heteroarylnitril groups for organic light emitting diodes |
US10693082B2 (en) | 2015-04-06 | 2020-06-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11818949B2 (en) | 2015-04-06 | 2023-11-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11495749B2 (en) | 2015-04-06 | 2022-11-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10777749B2 (en) | 2015-05-07 | 2020-09-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10403826B2 (en) | 2015-05-07 | 2019-09-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9478758B1 (en) | 2015-05-08 | 2016-10-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9859510B2 (en) | 2015-05-15 | 2018-01-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR101879415B1 (ko) * | 2015-05-20 | 2018-07-17 | 삼성에스디아이 주식회사 | 유기 화합물, 유기 광전자 소자 및 표시 장치 |
US10256411B2 (en) | 2015-05-21 | 2019-04-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10109799B2 (en) | 2015-05-21 | 2018-10-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10033004B2 (en) | 2015-06-01 | 2018-07-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10418568B2 (en) | 2015-06-01 | 2019-09-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
WO2016193243A1 (en) | 2015-06-03 | 2016-12-08 | Udc Ireland Limited | Highly efficient oled devices with very short decay times |
US11925102B2 (en) | 2015-06-04 | 2024-03-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10825997B2 (en) | 2015-06-25 | 2020-11-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10873036B2 (en) | 2015-07-07 | 2020-12-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9978956B2 (en) | 2015-07-15 | 2018-05-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11127905B2 (en) | 2015-07-29 | 2021-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11018309B2 (en) | 2015-08-03 | 2021-05-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11522140B2 (en) | 2015-08-17 | 2022-12-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10522769B2 (en) | 2015-08-18 | 2019-12-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10181564B2 (en) | 2015-08-26 | 2019-01-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10672996B2 (en) | 2015-09-03 | 2020-06-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11706972B2 (en) | 2015-09-08 | 2023-07-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11302872B2 (en) | 2015-09-09 | 2022-04-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10770664B2 (en) | 2015-09-21 | 2020-09-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20170092880A1 (en) | 2015-09-25 | 2017-03-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
WO2017056055A1 (en) | 2015-10-01 | 2017-04-06 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole carrying triazine groups for organic light emitting diodes |
EP3150606B1 (en) | 2015-10-01 | 2019-08-14 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazoles carrying benzofurane or benzothiophene groups for organic light emitting diodes |
US10847728B2 (en) | 2015-10-01 | 2020-11-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3150604B1 (en) | 2015-10-01 | 2021-07-14 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole carrying benzimidazolo[1,2-a]benzimidazolylyl groups, carbazolyl groups, benzofurane groups or benzothiophene groups for organic light emitting diodes |
US10593892B2 (en) | 2015-10-01 | 2020-03-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3356368B1 (en) | 2015-10-01 | 2021-07-21 | Idemitsu Kosan Co., Ltd | Benzimidazolo[1,2-a]benzimidazole carrying benzimidazolo[1,2-a]benzimidazolyl groups, carbazolyl groups, benzofurane groups or benzothiophene groups for organic light emitting diodes |
US10991895B2 (en) | 2015-10-06 | 2021-04-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10388893B2 (en) | 2015-10-29 | 2019-08-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10388892B2 (en) | 2015-10-29 | 2019-08-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10177318B2 (en) | 2015-10-29 | 2019-01-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR101614738B1 (ko) * | 2015-11-02 | 2016-04-22 | 덕산네오룩스 주식회사 | 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
US20180319813A1 (en) | 2015-11-04 | 2018-11-08 | Idemitsu Kosan Co., Ltd | Benzimidazole fused heteroaryls |
US10998507B2 (en) | 2015-11-23 | 2021-05-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR102617840B1 (ko) * | 2015-11-26 | 2023-12-26 | 덕산네오룩스 주식회사 | 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
US10476010B2 (en) | 2015-11-30 | 2019-11-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
WO2017093958A1 (en) | 2015-12-04 | 2017-06-08 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole derivatives for organic light emitting diodes |
WO2017109722A1 (en) | 2015-12-21 | 2017-06-29 | Idemitsu Kosan Co., Ltd. | Nitrogen-containing heterocyclic compounds and organic electroluminescence devices containing them |
US11024808B2 (en) | 2015-12-29 | 2021-06-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10957861B2 (en) | 2015-12-29 | 2021-03-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10135006B2 (en) | 2016-01-04 | 2018-11-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
JP6788314B2 (ja) | 2016-01-06 | 2020-11-25 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子の製造方法、表示装置及び照明装置 |
US10457864B2 (en) | 2016-02-09 | 2019-10-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20170229663A1 (en) | 2016-02-09 | 2017-08-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10707427B2 (en) | 2016-02-09 | 2020-07-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10600967B2 (en) | 2016-02-18 | 2020-03-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
GB2548337A (en) | 2016-03-08 | 2017-09-20 | Cambridge Display Tech Ltd | Compound, composition and organic light-emitting device |
US11094891B2 (en) | 2016-03-16 | 2021-08-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10276809B2 (en) | 2016-04-05 | 2019-04-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10236456B2 (en) | 2016-04-11 | 2019-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10968229B2 (en) | 2016-04-12 | 2021-04-06 | Idemitsu Kosan Co., Ltd. | Seven-membered ring compounds |
US10566552B2 (en) | 2016-04-13 | 2020-02-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11228003B2 (en) | 2016-04-22 | 2022-01-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11228002B2 (en) | 2016-04-22 | 2022-01-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11081647B2 (en) | 2016-04-22 | 2021-08-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN107056807B (zh) * | 2016-04-25 | 2019-06-07 | 中节能万润股份有限公司 | 一种以均苯为核心的化合物及其在有机电致发光器件中的应用 |
US10985328B2 (en) | 2016-05-25 | 2021-04-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10468609B2 (en) | 2016-06-02 | 2019-11-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10862054B2 (en) | 2016-06-20 | 2020-12-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10727423B2 (en) | 2016-06-20 | 2020-07-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10686140B2 (en) | 2016-06-20 | 2020-06-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10672997B2 (en) | 2016-06-20 | 2020-06-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10651403B2 (en) | 2016-06-20 | 2020-05-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11482683B2 (en) | 2016-06-20 | 2022-10-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10957866B2 (en) | 2016-06-30 | 2021-03-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9929360B2 (en) | 2016-07-08 | 2018-03-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10566547B2 (en) | 2016-07-11 | 2020-02-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10720587B2 (en) | 2016-07-19 | 2020-07-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10153443B2 (en) | 2016-07-19 | 2018-12-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
JP7071919B2 (ja) * | 2016-08-02 | 2022-05-19 | メルク パテント ゲーエムベーハー | 含窒素複素環化合物の製造方法及び含窒素複素環化合物 |
US10205105B2 (en) | 2016-08-15 | 2019-02-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10608186B2 (en) | 2016-09-14 | 2020-03-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10505127B2 (en) | 2016-09-19 | 2019-12-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10680187B2 (en) | 2016-09-23 | 2020-06-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11183642B2 (en) | 2016-10-03 | 2021-11-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11127906B2 (en) | 2016-10-03 | 2021-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11189804B2 (en) | 2016-10-03 | 2021-11-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11196010B2 (en) | 2016-10-03 | 2021-12-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11081658B2 (en) | 2016-10-03 | 2021-08-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11011709B2 (en) | 2016-10-07 | 2021-05-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11239432B2 (en) | 2016-10-14 | 2022-02-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10608185B2 (en) | 2016-10-17 | 2020-03-31 | Univeral Display Corporation | Organic electroluminescent materials and devices |
US10236458B2 (en) | 2016-10-24 | 2019-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20180130956A1 (en) | 2016-11-09 | 2018-05-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10340464B2 (en) | 2016-11-10 | 2019-07-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10680188B2 (en) | 2016-11-11 | 2020-06-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10897016B2 (en) | 2016-11-14 | 2021-01-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10964893B2 (en) | 2016-11-17 | 2021-03-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10662196B2 (en) | 2016-11-17 | 2020-05-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10153445B2 (en) | 2016-11-21 | 2018-12-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10833276B2 (en) | 2016-11-21 | 2020-11-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11555048B2 (en) | 2016-12-01 | 2023-01-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20200098995A1 (en) * | 2016-12-08 | 2020-03-26 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Polymer and electroluminescent device |
US10490753B2 (en) | 2016-12-15 | 2019-11-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11548905B2 (en) | 2016-12-15 | 2023-01-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11545636B2 (en) | 2016-12-15 | 2023-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10811618B2 (en) | 2016-12-19 | 2020-10-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11152579B2 (en) | 2016-12-28 | 2021-10-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11201298B2 (en) | 2017-01-09 | 2021-12-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11780865B2 (en) | 2017-01-09 | 2023-10-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10804475B2 (en) | 2017-01-11 | 2020-10-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11545637B2 (en) | 2017-01-13 | 2023-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10629820B2 (en) | 2017-01-18 | 2020-04-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11053268B2 (en) | 2017-01-20 | 2021-07-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10964904B2 (en) | 2017-01-20 | 2021-03-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11765968B2 (en) | 2017-01-23 | 2023-09-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11050028B2 (en) | 2017-01-24 | 2021-06-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3360945B1 (en) * | 2017-02-14 | 2019-04-24 | Cynora Gmbh | Organic electroluminescent device |
US10978647B2 (en) | 2017-02-15 | 2021-04-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10844084B2 (en) | 2017-02-22 | 2020-11-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10745431B2 (en) | 2017-03-08 | 2020-08-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10741780B2 (en) | 2017-03-10 | 2020-08-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10672998B2 (en) | 2017-03-23 | 2020-06-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10910577B2 (en) | 2017-03-28 | 2021-02-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10873037B2 (en) | 2017-03-28 | 2020-12-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11056658B2 (en) | 2017-03-29 | 2021-07-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11158820B2 (en) | 2017-03-29 | 2021-10-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10844085B2 (en) | 2017-03-29 | 2020-11-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10862046B2 (en) | 2017-03-30 | 2020-12-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11276829B2 (en) | 2017-03-31 | 2022-03-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11139443B2 (en) | 2017-03-31 | 2021-10-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11038117B2 (en) | 2017-04-11 | 2021-06-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10777754B2 (en) | 2017-04-11 | 2020-09-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR102458681B1 (ko) * | 2017-04-14 | 2022-10-26 | 삼성디스플레이 주식회사 | 헤테로시클릭 화합물 및 이를 포함한 유기 발광 소자 |
US11084838B2 (en) | 2017-04-21 | 2021-08-10 | Universal Display Corporation | Organic electroluminescent materials and device |
US10975113B2 (en) | 2017-04-21 | 2021-04-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11101434B2 (en) | 2017-04-21 | 2021-08-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10910570B2 (en) | 2017-04-28 | 2021-02-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11038137B2 (en) | 2017-04-28 | 2021-06-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11117897B2 (en) | 2017-05-01 | 2021-09-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10941170B2 (en) | 2017-05-03 | 2021-03-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11201299B2 (en) | 2017-05-04 | 2021-12-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10862055B2 (en) | 2017-05-05 | 2020-12-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10870668B2 (en) | 2017-05-05 | 2020-12-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10930864B2 (en) | 2017-05-10 | 2021-02-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10822362B2 (en) | 2017-05-11 | 2020-11-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10944060B2 (en) | 2017-05-11 | 2021-03-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10840459B2 (en) | 2017-05-18 | 2020-11-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10944062B2 (en) | 2017-05-18 | 2021-03-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10790455B2 (en) | 2017-05-18 | 2020-09-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11038115B2 (en) | 2017-05-18 | 2021-06-15 | Universal Display Corporation | Organic electroluminescent materials and device |
US10934293B2 (en) | 2017-05-18 | 2021-03-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10930862B2 (en) | 2017-06-01 | 2021-02-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11802136B2 (en) | 2017-06-23 | 2023-10-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11608321B2 (en) | 2017-06-23 | 2023-03-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11814403B2 (en) | 2017-06-23 | 2023-11-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11758804B2 (en) | 2017-06-23 | 2023-09-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11678565B2 (en) | 2017-06-23 | 2023-06-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11174259B2 (en) | 2017-06-23 | 2021-11-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11495757B2 (en) | 2017-06-23 | 2022-11-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11552261B2 (en) | 2017-06-23 | 2023-01-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11725022B2 (en) | 2017-06-23 | 2023-08-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10968226B2 (en) | 2017-06-23 | 2021-04-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11832510B2 (en) | 2017-06-23 | 2023-11-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20180370999A1 (en) | 2017-06-23 | 2018-12-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11469382B2 (en) | 2017-07-12 | 2022-10-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11228010B2 (en) | 2017-07-26 | 2022-01-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11239433B2 (en) | 2017-07-26 | 2022-02-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11322691B2 (en) | 2017-07-26 | 2022-05-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11968883B2 (en) | 2017-07-26 | 2024-04-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11917843B2 (en) | 2017-07-26 | 2024-02-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11765970B2 (en) | 2017-07-26 | 2023-09-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11744141B2 (en) | 2017-08-09 | 2023-08-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11744142B2 (en) | 2017-08-10 | 2023-08-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11508913B2 (en) | 2017-08-10 | 2022-11-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11910699B2 (en) | 2017-08-10 | 2024-02-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11349083B2 (en) | 2017-08-10 | 2022-05-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11462697B2 (en) | 2017-08-22 | 2022-10-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11723269B2 (en) | 2017-08-22 | 2023-08-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11437591B2 (en) | 2017-08-24 | 2022-09-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11605791B2 (en) | 2017-09-01 | 2023-03-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11424420B2 (en) | 2017-09-07 | 2022-08-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11696492B2 (en) | 2017-09-07 | 2023-07-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11444249B2 (en) | 2017-09-07 | 2022-09-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10608188B2 (en) | 2017-09-11 | 2020-03-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11778897B2 (en) | 2017-09-20 | 2023-10-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11214587B2 (en) | 2017-11-07 | 2022-01-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11910702B2 (en) | 2017-11-07 | 2024-02-20 | Universal Display Corporation | Organic electroluminescent devices |
US11183646B2 (en) | 2017-11-07 | 2021-11-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11168103B2 (en) | 2017-11-17 | 2021-11-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20190161504A1 (en) | 2017-11-28 | 2019-05-30 | University Of Southern California | Carbene compounds and organic electroluminescent devices |
US11825735B2 (en) | 2017-11-28 | 2023-11-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3492480B1 (en) | 2017-11-29 | 2021-10-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11937503B2 (en) | 2017-11-30 | 2024-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN111247133A (zh) * | 2017-12-14 | 2020-06-05 | 广州华睿光电材料有限公司 | 咔唑三苯有机化合物、高聚物、混合物、组合物及其应用 |
US11233205B2 (en) | 2017-12-14 | 2022-01-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10971687B2 (en) | 2017-12-14 | 2021-04-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11233204B2 (en) | 2017-12-14 | 2022-01-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11700765B2 (en) | 2018-01-10 | 2023-07-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11081659B2 (en) | 2018-01-10 | 2021-08-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11271177B2 (en) | 2018-01-11 | 2022-03-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11515493B2 (en) | 2018-01-11 | 2022-11-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11845764B2 (en) | 2018-01-26 | 2023-12-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11542289B2 (en) | 2018-01-26 | 2023-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11367840B2 (en) | 2018-01-26 | 2022-06-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11342509B2 (en) | 2018-02-09 | 2022-05-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11180519B2 (en) | 2018-02-09 | 2021-11-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11957050B2 (en) | 2018-02-09 | 2024-04-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11239434B2 (en) | 2018-02-09 | 2022-02-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11142538B2 (en) | 2018-03-12 | 2021-10-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11217757B2 (en) | 2018-03-12 | 2022-01-04 | Universal Display Corporation | Host materials for electroluminescent devices |
US11557733B2 (en) | 2018-03-12 | 2023-01-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11279722B2 (en) | 2018-03-12 | 2022-03-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11165028B2 (en) | 2018-03-12 | 2021-11-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR20190118073A (ko) | 2018-04-09 | 2019-10-17 | 삼성전자주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
US11390639B2 (en) | 2018-04-13 | 2022-07-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11882759B2 (en) | 2018-04-13 | 2024-01-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11616203B2 (en) | 2018-04-17 | 2023-03-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11342513B2 (en) | 2018-05-04 | 2022-05-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11515494B2 (en) | 2018-05-04 | 2022-11-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11753427B2 (en) | 2018-05-04 | 2023-09-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11793073B2 (en) | 2018-05-06 | 2023-10-17 | Universal Display Corporation | Host materials for electroluminescent devices |
US11450822B2 (en) | 2018-05-25 | 2022-09-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11459349B2 (en) | 2018-05-25 | 2022-10-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11716900B2 (en) | 2018-05-30 | 2023-08-01 | Universal Display Corporation | Host materials for electroluminescent devices |
US11296283B2 (en) | 2018-06-04 | 2022-04-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11925103B2 (en) | 2018-06-05 | 2024-03-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11339182B2 (en) | 2018-06-07 | 2022-05-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN110577523B (zh) * | 2018-06-07 | 2021-07-06 | 江苏三月科技股份有限公司 | 一种含三芳胺结构的化合物及其制备的有机电致发光器件 |
US11228004B2 (en) | 2018-06-22 | 2022-01-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11261207B2 (en) | 2018-06-25 | 2022-03-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11753425B2 (en) | 2018-07-11 | 2023-09-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR20200009834A (ko) | 2018-07-20 | 2020-01-30 | 삼성전자주식회사 | 축합환 화합물, 이를 포함한 조성물 및 이를 포함한 유기 발광 소자 |
US20200075870A1 (en) | 2018-08-22 | 2020-03-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11233203B2 (en) | 2018-09-06 | 2022-01-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11485706B2 (en) | 2018-09-11 | 2022-11-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11718634B2 (en) | 2018-09-14 | 2023-08-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11903305B2 (en) | 2018-09-24 | 2024-02-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11469383B2 (en) | 2018-10-08 | 2022-10-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11495752B2 (en) | 2018-10-08 | 2022-11-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11476430B2 (en) | 2018-10-15 | 2022-10-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11515482B2 (en) | 2018-10-23 | 2022-11-29 | Universal Display Corporation | Deep HOMO (highest occupied molecular orbital) emitter device structures |
US11469384B2 (en) | 2018-11-02 | 2022-10-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11825736B2 (en) | 2018-11-19 | 2023-11-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11963441B2 (en) | 2018-11-26 | 2024-04-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11889708B2 (en) | 2019-11-14 | 2024-01-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11690285B2 (en) | 2018-11-28 | 2023-06-27 | Universal Display Corporation | Electroluminescent devices |
US11716899B2 (en) | 2018-11-28 | 2023-08-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11672165B2 (en) | 2018-11-28 | 2023-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11672176B2 (en) | 2018-11-28 | 2023-06-06 | Universal Display Corporation | Host materials for electroluminescent devices |
US11706980B2 (en) | 2018-11-28 | 2023-07-18 | Universal Display Corporation | Host materials for electroluminescent devices |
US11623936B2 (en) | 2018-12-11 | 2023-04-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11737349B2 (en) | 2018-12-12 | 2023-08-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11834459B2 (en) | 2018-12-12 | 2023-12-05 | Universal Display Corporation | Host materials for electroluminescent devices |
KR20210103508A (ko) * | 2018-12-14 | 2021-08-23 | 이데미쓰 고산 가부시키가이샤 | 유기 일렉트로루미네센스 소자, 화합물, 유기 일렉트로루미네센스 소자용 재료, 및 전자 기기 |
US11812624B2 (en) | 2019-01-30 | 2023-11-07 | The University Of Southern California | Organic electroluminescent materials and devices |
US11780829B2 (en) | 2019-01-30 | 2023-10-10 | The University Of Southern California | Organic electroluminescent materials and devices |
US20200251664A1 (en) | 2019-02-01 | 2020-08-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11370809B2 (en) | 2019-02-08 | 2022-06-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11325932B2 (en) | 2019-02-08 | 2022-05-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11773320B2 (en) | 2019-02-21 | 2023-10-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11871653B2 (en) | 2019-02-22 | 2024-01-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11557738B2 (en) | 2019-02-22 | 2023-01-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11512093B2 (en) | 2019-03-04 | 2022-11-29 | Universal Display Corporation | Compound used for organic light emitting device (OLED), consumer product and formulation |
KR20200108955A (ko) * | 2019-03-11 | 2020-09-22 | 삼성디스플레이 주식회사 | 헤테로시클릭 화합물 및 이를 포함한 유기 발광 소자 |
US11739081B2 (en) | 2019-03-11 | 2023-08-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11637261B2 (en) | 2019-03-12 | 2023-04-25 | Universal Display Corporation | Nanopatch antenna outcoupling structure for use in OLEDs |
US20200295291A1 (en) | 2019-03-12 | 2020-09-17 | Universal Display Corporation | OLED WITH TRIPLET EMITTER AND EXCITED STATE LIFETIME LESS THAN 200 ns |
US11569480B2 (en) | 2019-03-12 | 2023-01-31 | Universal Display Corporation | Plasmonic OLEDs and vertical dipole emitters |
US11963438B2 (en) | 2019-03-26 | 2024-04-16 | The University Of Southern California | Organic electroluminescent materials and devices |
JP2020158491A (ja) | 2019-03-26 | 2020-10-01 | ユニバーサル ディスプレイ コーポレイション | 有機エレクトロルミネセンス材料及びデバイス |
US11639363B2 (en) | 2019-04-22 | 2023-05-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11613550B2 (en) | 2019-04-30 | 2023-03-28 | Universal Display Corporation | Organic electroluminescent materials and devices comprising benzimidazole-containing metal complexes |
US11560398B2 (en) | 2019-05-07 | 2023-01-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11495756B2 (en) | 2019-05-07 | 2022-11-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11827651B2 (en) | 2019-05-13 | 2023-11-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11634445B2 (en) | 2019-05-21 | 2023-04-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
US12010859B2 (en) | 2019-05-24 | 2024-06-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN111978297A (zh) * | 2019-05-24 | 2020-11-24 | 北京大学深圳研究生院 | 一种有机电致发光材料及其制备方法与应用 |
US11647667B2 (en) | 2019-06-14 | 2023-05-09 | Universal Display Corporation | Organic electroluminescent compounds and organic light emitting devices using the same |
US11920070B2 (en) | 2019-07-12 | 2024-03-05 | The University Of Southern California | Luminescent janus-type, two-coordinated metal complexes |
US11926638B2 (en) | 2019-07-22 | 2024-03-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11685754B2 (en) | 2019-07-22 | 2023-06-27 | Universal Display Corporation | Heteroleptic organic electroluminescent materials |
US20210032278A1 (en) | 2019-07-30 | 2021-02-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11708355B2 (en) | 2019-08-01 | 2023-07-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11985888B2 (en) | 2019-08-12 | 2024-05-14 | The Regents Of The University Of Michigan | Organic electroluminescent device |
US11374181B2 (en) | 2019-08-14 | 2022-06-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11930699B2 (en) | 2019-08-15 | 2024-03-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20210047354A1 (en) | 2019-08-16 | 2021-02-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11925105B2 (en) | 2019-08-26 | 2024-03-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11937494B2 (en) | 2019-08-28 | 2024-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11600787B2 (en) | 2019-08-30 | 2023-03-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11820783B2 (en) | 2019-09-06 | 2023-11-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN112479978B (zh) * | 2019-09-11 | 2023-11-28 | 江苏三月科技股份有限公司 | 一种以咔唑衍生物为核心的有机化合物及其应用 |
KR102436480B1 (ko) * | 2019-09-25 | 2022-08-25 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
US20210098717A1 (en) | 2019-09-26 | 2021-04-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11864458B2 (en) | 2019-10-08 | 2024-01-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11950493B2 (en) | 2019-10-15 | 2024-04-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11697653B2 (en) | 2019-10-21 | 2023-07-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11919914B2 (en) | 2019-10-25 | 2024-03-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11765965B2 (en) | 2019-10-30 | 2023-09-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20210135130A1 (en) | 2019-11-04 | 2021-05-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
JP7488091B2 (ja) | 2019-11-14 | 2024-05-21 | ユニバーサル ディスプレイ コーポレイション | 有機エレクトロルミネセンス材料及びデバイス |
KR20210076220A (ko) * | 2019-12-12 | 2021-06-24 | 삼성디스플레이 주식회사 | 유기 발광 소자 및 이를 포함하는 장치 |
US20210217969A1 (en) | 2020-01-06 | 2021-07-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11778895B2 (en) | 2020-01-13 | 2023-10-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11917900B2 (en) | 2020-01-28 | 2024-02-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220336759A1 (en) | 2020-01-28 | 2022-10-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11932660B2 (en) | 2020-01-29 | 2024-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
JP7367574B2 (ja) * | 2020-03-16 | 2023-10-24 | 三菱ケミカル株式会社 | 芳香族化合物 |
US11970508B2 (en) | 2020-04-22 | 2024-04-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3937268A1 (en) | 2020-07-10 | 2022-01-12 | Universal Display Corporation | Plasmonic oleds and vertical dipole emitters |
US20220158096A1 (en) | 2020-11-16 | 2022-05-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220165967A1 (en) | 2020-11-24 | 2022-05-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220162243A1 (en) | 2020-11-24 | 2022-05-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220271241A1 (en) | 2021-02-03 | 2022-08-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4059915A3 (en) | 2021-02-26 | 2022-12-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4060758A3 (en) | 2021-02-26 | 2023-03-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220298192A1 (en) | 2021-03-05 | 2022-09-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220298190A1 (en) | 2021-03-12 | 2022-09-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220298193A1 (en) | 2021-03-15 | 2022-09-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220340607A1 (en) | 2021-04-05 | 2022-10-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4075531A1 (en) | 2021-04-13 | 2022-10-19 | Universal Display Corporation | Plasmonic oleds and vertical dipole emitters |
US20220352478A1 (en) | 2021-04-14 | 2022-11-03 | Universal Display Corporation | Organic eletroluminescent materials and devices |
US20220407020A1 (en) | 2021-04-23 | 2022-12-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20230006149A1 (en) | 2021-04-23 | 2023-01-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20230133787A1 (en) | 2021-06-08 | 2023-05-04 | University Of Southern California | Molecular Alignment of Homoleptic Iridium Phosphors |
EP4151699A1 (en) | 2021-09-17 | 2023-03-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4212539A1 (en) | 2021-12-16 | 2023-07-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20230292592A1 (en) | 2022-03-09 | 2023-09-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
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Citations (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002308837A (ja) * | 2001-04-05 | 2002-10-23 | Fuji Photo Film Co Ltd | 新規化合物、およびそれを用いた発光素子 |
JP2005112765A (ja) * | 2003-10-07 | 2005-04-28 | Mitsui Chemicals Inc | 複素環化合物および該化合物を含有する有機電界発光素子 |
WO2006128800A1 (en) * | 2005-05-30 | 2006-12-07 | Ciba Specialty Chemicals Holding Inc. | Electroluminescent device |
WO2006137210A1 (ja) * | 2005-06-24 | 2006-12-28 | Idemitsu Kosan Co., Ltd. | ベンゾチオフェン誘導体及びそれを利用した有機エレクトロルミネッセンス素子 |
JP2007088307A (ja) * | 2005-09-22 | 2007-04-05 | Toyota Central Res & Dev Lab Inc | 電界発光素子 |
WO2007077810A1 (ja) * | 2006-01-05 | 2007-07-12 | 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 |
JP2007189001A (ja) * | 2006-01-12 | 2007-07-26 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子材料、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 |
JP2007288035A (ja) * | 2006-04-19 | 2007-11-01 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子材料、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 |
JP2008060379A (ja) * | 2006-08-31 | 2008-03-13 | Mitsui Chemicals Inc | 有機電界発光素子および芳香族化合物 |
JP2008084913A (ja) * | 2006-09-26 | 2008-04-10 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、表示装置および照明装置 |
WO2008072596A1 (ja) * | 2006-12-13 | 2008-06-19 | 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 |
WO2008075517A1 (ja) * | 2006-12-18 | 2008-06-26 | Konica Minolta Holdings, Inc. | 多色燐光発光有機エレクトロルミネッセンス素子及び照明装置 |
JP2008159741A (ja) * | 2006-12-22 | 2008-07-10 | Konica Minolta Holdings Inc | 発光体 |
JP2008181937A (ja) * | 2007-01-23 | 2008-08-07 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子及び照明装置 |
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 |
Family Cites Families (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS519485A (ja) | 1974-07-15 | 1976-01-26 | Mitsubishi Heavy Ind Ltd | Kihosokudokeisokuho |
JPH05109485A (ja) | 1991-10-15 | 1993-04-30 | Ricoh Co Ltd | 電界発光素子 |
JP3266573B2 (ja) * | 1998-04-08 | 2002-03-18 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子 |
DE60143106D1 (de) * | 2000-07-17 | 2010-11-04 | Fujifilm Corp | Lichtemittierendes Element und Azolverbindung |
JP2004002351A (ja) | 2002-03-27 | 2004-01-08 | Tdk Corp | 有機el素子 |
JP4265219B2 (ja) * | 2003-01-06 | 2009-05-20 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子および表示装置 |
WO2004096945A1 (ja) | 2003-05-01 | 2004-11-11 | Fujitsu Limited | 1,3,6,8−四置換ピレン化合物、有機el素子及び有機elディスプレイ |
TWI354011B (en) | 2003-05-16 | 2011-12-11 | Semiconductor Energy Lab | Carbazole derivative, organic semiconductor elemen |
JP4661781B2 (ja) | 2004-04-14 | 2011-03-30 | コニカミノルタホールディングス株式会社 | 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 |
JP4384536B2 (ja) | 2004-04-27 | 2009-12-16 | 三井化学株式会社 | アントラセン化合物、および該アントラセン化合物を含有する有機電界発光素子 |
TWI373506B (en) | 2004-05-21 | 2012-10-01 | Toray Industries | Light-emitting element material and light-emitting material |
KR101249234B1 (ko) | 2004-12-08 | 2013-04-01 | 코닌클리즈케 필립스 일렉트로닉스 엔.브이. | 인광 방출체에 대한 호스트 매트릭스로서 반도체 재료에사용하기 위한 9,9'- 및 2,2'-치환 3,3'-바이카르바졸릴유도체 |
US7504769B2 (en) * | 2004-12-16 | 2009-03-17 | E. I. Du Pont De Nemours + Company | Aromatic chalcogen compounds and their use |
GB2439030B (en) | 2005-04-18 | 2011-03-02 | Konica Minolta Holdings Inc | Organic electroluminescent device, display and illuminating device |
US20080166594A1 (en) | 2005-06-24 | 2008-07-10 | Idemitsu Kosan Co., Ltd. | Benzothiophene derivative and organic electroluminescence device making use of the same |
JP4807013B2 (ja) | 2005-09-02 | 2011-11-02 | 東レ株式会社 | 発光素子材料および発光素子 |
JP2007110097A (ja) | 2005-09-14 | 2007-04-26 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子の製造方法、表示装置及び照明装置 |
JP4726584B2 (ja) | 2005-09-15 | 2011-07-20 | 三井化学株式会社 | 芳香族化合物、該芳香族化合物を含有する有機電界発光素子 |
US7651791B2 (en) | 2005-12-15 | 2010-01-26 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescence device and electroluminescence device employing the same |
TW200726317A (en) | 2005-12-30 | 2007-07-01 | Toyo Ink Mfg Co | Organic electroluminescent device |
EP1998387B1 (en) * | 2006-03-17 | 2015-04-22 | Konica Minolta Holdings, Inc. | Organic electroluminescent device, display and illuminating device |
JP5683784B2 (ja) * | 2006-03-23 | 2015-03-11 | コニカミノルタ株式会社 | 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 |
US20070224446A1 (en) | 2006-03-24 | 2007-09-27 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescence device and organic electroluminescence device using the same |
CN101627102B (zh) * | 2007-03-07 | 2013-08-28 | 东丽株式会社 | 发光元件材料和发光元件 |
WO2008143229A1 (ja) * | 2007-05-21 | 2008-11-27 | Idemitsu Kosan Co., Ltd. | アントラセン誘導体及びそれを利用した有機エレクトロルミネッセンス素子 |
KR101453128B1 (ko) | 2007-07-10 | 2014-10-27 | 이데미쓰 고산 가부시키가이샤 | 유기 전기발광 소자용 재료 및 그것을 이용한 유기 전기발광 소자 |
US8080658B2 (en) | 2007-07-10 | 2011-12-20 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescent element and organic electroluminescent element employing the same |
-
2007
- 2007-11-21 KR KR1020107000442A patent/KR101453128B1/ko active IP Right Grant
- 2007-11-21 US US11/943,934 patent/US7968213B2/en active Active
- 2007-11-21 WO PCT/JP2007/072585 patent/WO2009008099A1/ja active Application Filing
- 2007-11-21 KR KR1020107000441A patent/KR20100032888A/ko not_active Application Discontinuation
- 2007-11-21 JP JP2009522494A patent/JP5619418B2/ja active Active
- 2007-11-21 EP EP07832316.9A patent/EP2166584B1/en active Active
- 2007-11-21 JP JP2009522493A patent/JPWO2009008099A1/ja active Pending
- 2007-11-21 EP EP07832315A patent/EP2166583A4/en not_active Withdrawn
- 2007-11-21 US US11/943,879 patent/US8114530B2/en active Active
- 2007-11-21 TW TW096144139A patent/TW200903877A/zh unknown
- 2007-11-21 WO PCT/JP2007/072586 patent/WO2009008100A1/ja active Application Filing
- 2007-11-21 TW TW096144126A patent/TW200902675A/zh unknown
-
2012
- 2012-01-03 US US13/342,778 patent/US9209410B2/en active Active
Patent Citations (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002308837A (ja) * | 2001-04-05 | 2002-10-23 | Fuji Photo Film Co Ltd | 新規化合物、およびそれを用いた発光素子 |
JP2005112765A (ja) * | 2003-10-07 | 2005-04-28 | Mitsui Chemicals Inc | 複素環化合物および該化合物を含有する有機電界発光素子 |
WO2006128800A1 (en) * | 2005-05-30 | 2006-12-07 | Ciba Specialty Chemicals Holding Inc. | Electroluminescent device |
WO2006137210A1 (ja) * | 2005-06-24 | 2006-12-28 | Idemitsu Kosan Co., Ltd. | ベンゾチオフェン誘導体及びそれを利用した有機エレクトロルミネッセンス素子 |
JP2007088307A (ja) * | 2005-09-22 | 2007-04-05 | Toyota Central Res & Dev Lab Inc | 電界発光素子 |
WO2007077810A1 (ja) * | 2006-01-05 | 2007-07-12 | 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 |
JP2007189001A (ja) * | 2006-01-12 | 2007-07-26 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子材料、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 |
JP2007288035A (ja) * | 2006-04-19 | 2007-11-01 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子材料、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 |
JP2008060379A (ja) * | 2006-08-31 | 2008-03-13 | Mitsui Chemicals Inc | 有機電界発光素子および芳香族化合物 |
JP2008084913A (ja) * | 2006-09-26 | 2008-04-10 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、表示装置および照明装置 |
WO2008072596A1 (ja) * | 2006-12-13 | 2008-06-19 | 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 |
WO2008075517A1 (ja) * | 2006-12-18 | 2008-06-26 | Konica Minolta Holdings, Inc. | 多色燐光発光有機エレクトロルミネッセンス素子及び照明装置 |
JP2008159741A (ja) * | 2006-12-22 | 2008-07-10 | Konica Minolta Holdings Inc | 発光体 |
JP2008181937A (ja) * | 2007-01-23 | 2008-08-07 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子及び照明装置 |
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 |
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KR20100032888A (ko) | 2010-03-26 |
KR20100031736A (ko) | 2010-03-24 |
EP2166583A1 (en) | 2010-03-24 |
JP5619418B2 (ja) | 2014-11-05 |
TW200902675A (en) | 2009-01-16 |
EP2166583A4 (en) | 2011-10-19 |
EP2166584A4 (en) | 2011-10-26 |
WO2009008100A1 (ja) | 2009-01-15 |
EP2166584A1 (en) | 2010-03-24 |
US7968213B2 (en) | 2011-06-28 |
WO2009008099A1 (ja) | 2009-01-15 |
US20090017330A1 (en) | 2009-01-15 |
TW200903877A (en) | 2009-01-16 |
US20090017331A1 (en) | 2009-01-15 |
US8114530B2 (en) | 2012-02-14 |
JPWO2009008100A1 (ja) | 2010-09-02 |
US9209410B2 (en) | 2015-12-08 |
EP2166584B1 (en) | 2016-06-08 |
KR101453128B1 (ko) | 2014-10-27 |
US20120097937A1 (en) | 2012-04-26 |
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