CN105367544A - 含苯并[9,10]菲的苯并稠合的噻吩或苯并稠合的呋喃化合物 - Google Patents
含苯并[9,10]菲的苯并稠合的噻吩或苯并稠合的呋喃化合物 Download PDFInfo
- Publication number
- CN105367544A CN105367544A CN201510646336.XA CN201510646336A CN105367544A CN 105367544 A CN105367544 A CN 105367544A CN 201510646336 A CN201510646336 A CN 201510646336A CN 105367544 A CN105367544 A CN 105367544A
- Authority
- CN
- China
- Prior art keywords
- benzo
- compound
- mixture
- layer
- luxuriant
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 title abstract 3
- 125000005580 triphenylene group Chemical group 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 90
- 239000010410 layer Substances 0.000 claims description 92
- 125000005605 benzo group Chemical group 0.000 claims description 81
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 40
- 239000012044 organic layer Substances 0.000 claims description 33
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 30
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 22
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 20
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 239000004305 biphenyl Substances 0.000 claims description 13
- 125000005561 phenanthryl group Chemical group 0.000 claims description 13
- 235000010290 biphenyl Nutrition 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 229910052741 iridium Inorganic materials 0.000 claims description 4
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 3
- 239000000463 material Substances 0.000 abstract description 65
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract description 44
- 229930192474 thiophene Natural products 0.000 abstract description 23
- 150000002240 furans Chemical class 0.000 abstract description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 108
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 90
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 88
- 239000000203 mixture Substances 0.000 description 87
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 60
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
- 230000015572 biosynthetic process Effects 0.000 description 47
- 239000003205 fragrance Substances 0.000 description 47
- 238000003786 synthesis reaction Methods 0.000 description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
- 239000007787 solid Substances 0.000 description 41
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 34
- 239000000047 product Substances 0.000 description 34
- 229910052757 nitrogen Inorganic materials 0.000 description 30
- 239000012299 nitrogen atmosphere Substances 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 30
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 27
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
- 239000000243 solution Substances 0.000 description 26
- 238000003756 stirring Methods 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000010992 reflux Methods 0.000 description 21
- 239000004327 boric acid Substances 0.000 description 18
- -1 furan compound Chemical class 0.000 description 17
- 239000012265 solid product Substances 0.000 description 16
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 16
- 239000003480 eluent Substances 0.000 description 15
- 239000002019 doping agent Substances 0.000 description 14
- 238000000746 purification Methods 0.000 description 14
- 238000001953 recrystallisation Methods 0.000 description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
- 150000003384 small molecules Chemical class 0.000 description 12
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 12
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 238000000151 deposition Methods 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 11
- 238000010898 silica gel chromatography Methods 0.000 description 11
- 230000005540 biological transmission Effects 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 238000001914 filtration Methods 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 238000000605 extraction Methods 0.000 description 8
- 230000006872 improvement Effects 0.000 description 8
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 7
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 239000011368 organic material Substances 0.000 description 7
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 7
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 7
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000000412 dendrimer Substances 0.000 description 6
- 229920000736 dendritic polymer Polymers 0.000 description 6
- 230000008021 deposition Effects 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 229910052763 palladium Inorganic materials 0.000 description 6
- 230000027756 respiratory electron transport chain Effects 0.000 description 6
- 238000002390 rotary evaporation Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 5
- 235000019798 tripotassium phosphate Nutrition 0.000 description 5
- IJICRIUYZZESMW-UHFFFAOYSA-N 2-bromodibenzothiophene Chemical compound C1=CC=C2C3=CC(Br)=CC=C3SC2=C1 IJICRIUYZZESMW-UHFFFAOYSA-N 0.000 description 4
- 0 CC1C(*)=CC2=C(*)*C(*)=C2C=C1 Chemical compound CC1C(*)=CC2=C(*)*C(*)=C2C=C1 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 4
- NLLGFYPSWCMUIV-UHFFFAOYSA-N (3-methoxyphenyl)boronic acid Chemical compound COC1=CC=CC(B(O)O)=C1 NLLGFYPSWCMUIV-UHFFFAOYSA-N 0.000 description 3
- WNEXSUAHKVAPFK-UHFFFAOYSA-N 2,8-dibromodibenzothiophene Chemical compound C1=C(Br)C=C2C3=CC(Br)=CC=C3SC2=C1 WNEXSUAHKVAPFK-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- BLDFKEFDGIYYFJ-UHFFFAOYSA-N [2-(2,6-dimethoxyphenyl)phenyl]phosphonic acid Chemical group P(=O)(O)(O)C1=C(C=CC=C1)C1=C(C=CC=C1OC)OC BLDFKEFDGIYYFJ-UHFFFAOYSA-N 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 3
- 235000011056 potassium acetate Nutrition 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 235000015320 potassium carbonate Nutrition 0.000 description 3
- 229910000160 potassium phosphate Inorganic materials 0.000 description 3
- 229940093916 potassium phosphate Drugs 0.000 description 3
- 235000011009 potassium phosphates Nutrition 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000002207 thermal evaporation Methods 0.000 description 3
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 2
- GBRJZKUMODPNGR-UHFFFAOYSA-N 1-methoxy-3-(3-methoxyphenyl)-2-phenylbenzene Chemical group COC1=CC=CC(C=2C(=C(OC)C=CC=2)C=2C=CC=CC=2)=C1 GBRJZKUMODPNGR-UHFFFAOYSA-N 0.000 description 2
- FILKGCRCWDMBKA-UHFFFAOYSA-N 2,6-dichloropyridine Chemical compound ClC1=CC=CC(Cl)=N1 FILKGCRCWDMBKA-UHFFFAOYSA-N 0.000 description 2
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 description 2
- BMCNAHBDZUYGJG-UHFFFAOYSA-N 4-phenyldibenzothiophene Chemical compound C1=CC=CC=C1C1=CC=CC2=C1SC1=CC=CC=C12 BMCNAHBDZUYGJG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 230000004807 localization Effects 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 238000010129 solution processing Methods 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 125000001806 thionaphthenyl group Chemical group 0.000 description 2
- 238000003828 vacuum filtration Methods 0.000 description 2
- UEOCICLWNYTZBO-UHFFFAOYSA-N (3-methoxyphenoxy)boronic acid Chemical compound COC1=CC=CC(OB(O)O)=C1 UEOCICLWNYTZBO-UHFFFAOYSA-N 0.000 description 1
- VOAAEKKFGLPLLU-UHFFFAOYSA-N (4-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1 VOAAEKKFGLPLLU-UHFFFAOYSA-N 0.000 description 1
- DCGQVDFBDSTUML-AWEZNQCLSA-N 2-[(3S)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxypiperidine-1-carbonyl]chromen-4-one Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)O[C@@H]1CN(CCC1)C(=O)C=1OC2=CC=CC=C2C(C=1)=O DCGQVDFBDSTUML-AWEZNQCLSA-N 0.000 description 1
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical compound C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- 150000005360 2-phenylpyridines Chemical class 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- KIPMGYUMSNUPKH-UHFFFAOYSA-N 4-methoxy-1-(4-methoxyphenyl)-2-phenylbenzene Chemical group C1=CC(OC)=CC=C1C1=CC=C(OC)C=C1C1=CC=CC=C1 KIPMGYUMSNUPKH-UHFFFAOYSA-N 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- AZUOEBJBNCJYGA-JQIJEIRASA-N C=C/C(/c1ccccc1)=C\C(C1=CC=CCC1)=C Chemical compound C=C/C(/c1ccccc1)=C\C(C1=CC=CCC1)=C AZUOEBJBNCJYGA-JQIJEIRASA-N 0.000 description 1
- GTPBIVBFUOMIBT-UHFFFAOYSA-N COc1ccc(c2ccccc2c(cc2)c3cc2OC)c3c1 Chemical compound COc1ccc(c2ccccc2c(cc2)c3cc2OC)c3c1 GTPBIVBFUOMIBT-UHFFFAOYSA-N 0.000 description 1
- XEVPOWRQDJVRIX-LGPPOTRQSA-N C[C@@H]([C@@H](C)C([C@H](C1)O)=C1c(cccc1)c1C1=C)C1O Chemical compound C[C@@H]([C@@H](C)C([C@H](C1)O)=C1c(cccc1)c1C1=C)C1O XEVPOWRQDJVRIX-LGPPOTRQSA-N 0.000 description 1
- QKYCQQYRORPEFH-BBBLOLIVSA-N C[C@@H]1[C@H](C)C=CC(C)(C)[C@H]1C Chemical compound C[C@@H]1[C@H](C)C=CC(C)(C)[C@H]1C QKYCQQYRORPEFH-BBBLOLIVSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical class C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- 235000013325 dietary fiber Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RBBOWEDMXHTEPA-UHFFFAOYSA-N hexane;toluene Chemical compound CCCCCC.CC1=CC=CC=C1 RBBOWEDMXHTEPA-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- WGLLSSPDPJPLOR-UHFFFAOYSA-N tetramethylethylene Natural products CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/38—Polycyclic condensed hydrocarbons containing four rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/72—Benzo[c]thiophenes; Hydrogenated benzo[c]thiophenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/18—Carrier blocking layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
本发明提供了含苯并[9,10]菲的苯并稠合的噻吩化合物。另外，本发明提供了含苯并[9,10]菲的苯并稠合的呋喃化合物。所述化合物可以用于有机发光器件，特别是用作这样的器件的发射层中的主体，或用作这样的器件中的增进层材料，或用作二者。
Description
本申请是申请日为2008年8月7日、申请号为200880106949.2、发明名称为“含苯并[9,10]菲的苯并稠合的噻吩或苯并稠合的呋喃化合”的中国发明专利申请(PCT/US2008/072499)的分案申请。
母案申请要求2007年8月8日提交的美国临时申请序列号60/963,944，2007年12月28日提交的美国临时申请序列号61/017,506和2007年12月28日提交的美国临时申请序列号61/017,391的优先权权益，它们的内容通过引用整体明确结合到本申请中。本申请还涉及2007年12月28日提交的国际申请序列号PCT/US07/89131。
所要求保护的发明是由一个或多个如下联合的大学公司研究协议当事人、代表这些当事人和/或与这些当事人相关而完成的：密歇根大学理事会，普林斯顿大学，南加州大学和UniversalDisplayCorporation。所述协议在所要求保护的发明完成日和之前是有效的，并且所要求保护的发明是作为在所述协议的范围内采取的行动的结果而完成的。
发明领域
本发明涉及具有苯并稠合的噻吩和/或苯并稠合的呋喃以及苯并[9,10]菲的新型有机材料。特别地，所述材料具有二苯并噻吩和/或苯并呋喃以及苯并[9,10]菲。所述材料可以被用于发光器件(OLED)。
背景技术
利用有机材料的光电器件由于许多理由越来越为人们所需求。用于制造此类器件的许多材料是相对便宜的，因此有机光电器件具有在成本上比无机器件有优势的可能。另外，有机材料的固有性能如它们的柔性可以使得它们非常适合于特殊应用，如在柔性基材上制造。有机光电器件的例子包括有机发光器件(OLED)、有机光敏晶体管、有机光生伏打电池和有机光检测器。对于OLED，有机材料可以比常规材料有性能优势。例如，有机发射层发光的波长一般可以容易地用合适的掺杂剂调节。
OLED利用薄的有机膜，当对器件施加电压时所述有机膜会发光。OLED正在成为人们越来越感兴趣的技术，用于诸如平板显示器、照明和逆光照明之类的应用中。几种OLED材料和构造已被描述在美国专利5,844,363、6,303,238和5,707,745中，它们的全部内容通过引用结合在本文中。
磷光发射分子的一个应用是全色显示器。这样的显示器的工业标准要求适合发射被称为“饱和”色的特定颜色的像素。特别地，这些标准要求饱和的红、绿和蓝色像素。颜色可以使用本领域中公知的CIE坐标度量。
绿色发射分子的一个实例是三(2-苯基吡啶)合铱，表示为Ir(ppy)3，其具有如下结构:
在该图和本文中后面的图中，我们将由氮至金属(在这里为Ir)的配价键描绘为直线。
在这里使用的术语“有机”包括可用来制造有机光电器件的聚合物材料以及小分子有机材料。“小分子”指不是聚合物的任何有机材料，并且“小分子”实际上可以是相当大的。在一些情况下小分子可以包括重复单元。例如，使用长链烷基作为取代基不会将一个分子从“小分子”类型中排除。小分子也可以被引入聚合物中，例如作为在聚合物骨架上的侧基或作为骨架的一部分。小分子也可以用作树状分子的芯结构部分，该树状分子由在芯结构部分上构建的一系列化学壳组成。树状分子的芯结构部分可以是荧光或磷光小分子发射体。树状分子可以是“小分子”，并且据信目前在OLED领域中使用的所有树状分子是小分子。
在这里使用的“顶部”指最远离基材，而“底部”指最接近基材。当第一层被描述为“布置在”第二层上，所述第一层远离基材来设置。在所述第一和第二层之间可以有其它层，除非规定所述第一层与所述第二层“接触”。例如，阴极可以被描述为“布置在”阳极上，即使在两者之间有各种有机层。
在这里使用的“可溶液处理的”是指能够在液体介质中溶解、分散或输送和/或从液体介质中沉积，无论呈溶液或悬浮液的形式。
当据信一个配位体对发光材料的光活性性能有贡献时，该配位体被称为“光活性的”。
关于OLED和上述定义的更多细节可以见美国专利7,279,704号，该专利的全部内容通过引用结合在本文中。
发明概述
本发明提供了含苯并[9,10]菲的苯并稠合的噻吩化合物。所述化合物可以用于有机发光器件。所述化合物特别可以用作有机发光器件的发射层的主体，用作增进层(enhancementlayer)材料，或用作二者。
含苯并[9,10]菲的苯并稠合的噻吩的实例包括具有式(I)、式(II)和式(III)的结构的化合物:
R1、R2和R3独立地选自烷基、烷氧基、氨基、烯基、炔基、芳烷基、芳基、杂芳基和氢。R1、R2和R3各自可以表示多个取代基。R1、R2和R3中至少一个包括苯并[9,10]菲基团。所述苯并[9,10]菲基团可以直接连接到式(I)、(II)或(III)的结构上，但是在所述苯并[9,10]菲基团和所述式(I)、(II)或(III)的结构之间也可以有“间隔基”。
含苯并[9,10]菲的苯并稠合的噻吩或苯并稠合的呋喃的实例包括具有以下结构的化合物:
X是S或O。优选地，R1、R2和R3是非稠合的取代基，其独立地选自CnH2n+1，OCnH2n+1，OAr1，N(CnH2n+1)2，N(Ar1)(Ar2)，CH＝CH-CnH2n+1，C≡CHCnH2n+1，Ar1，Ar1-Ar2，CnH2n-Ar1，或者无取代。R1、R2和R3各自可以表示单、二、三或四取代。n是1，2，3，4，5，6，7，8，9或10。Ar1和Ar2独立地选自苯、联苯、萘、苯并[9,10]菲、咔唑和它们的杂芳族类似物。R1、R2和R3中至少一个包括苯并[9,10]菲基团。
有用的含苯并[9,10]菲的苯并稠合的噻吩化合物和含苯并[9,10]菲的苯并稠合的呋喃化合物的更具体的实例包括本文中公开的化合物1G-48G和化合物1-48。所述化合物可以用作有机发光器件的发射层的主体，这样的器件的增进层材料，或二者。
附图简要说明
图1显示了一种有机发光器件。
图2显示了一种不具有单独的电子传输层的颠倒的有机发光器件。
图3显示了含苯并[9,10]菲的苯并稠合的噻吩和/或苯并稠合的呋喃化合物。
详细描述
一般地，OLED包括布置在阳极和阴极之间并且电连接到阳极和阴极上的至少一个有机层。当施加电流时，阳极注入空穴和阴极注入电子到所述有机层中。注入的空穴和电子各自向着带相反电荷的电极迁移。当电子和空穴定域在同一分子上时，形成了“激子”，所述激子是具有激发能态的定域的电子-空穴对。当激子通过光发射机理松驰时，光被发射。在一些情况下，所述激子可以定域在受激准分子或激态复合物上。非辐射机理如热弛豫也可能发生，但一般被认为是不希望的。
最初的OLED采用从发射分子的单线态发光(“荧光”)的发射分子，例如在美国专利4,769,292号中公开的，该专利全部内容通过引用结合到本文中。荧光发射通常在小于10毫微秒的时间范围内发生。
最近，已经证实了具有从三重态发光(“磷光”)的发射材料的OLED。Baldo等人，“HighlyEfficientPhosphorescentEmissionfromOrganicElectroluminescentDevices”，Nature，395卷，151-154，1998(“Baldo-I”)；和Baldo等人，“Veryhigh-efficiencygreenorganiclight-emittingdevicesbasedonelectrophosphorescence”，Appl.Phys.Lett.，75卷，第3期，4-6(1999)(“Baldo-II”)，它们的全部内容通过引用结合在本文中。磷光被更详细地描述在美国专利7,279,704号5-6栏中，所述内容通过引用结合在本文中。
图1显示了有机发光器件100。所述附图不一定按比例画出。器件100可包括基材110，阳极115，空穴注入层120，空穴传输层125，电子封闭层130，发射层135，空穴封闭层140，电子传输层145，电子注入层150，保护层155，和阴极160。阴极160是具有第一导电层162和第二导电层164的复合阴极。器件100可以通过按照顺序沉积所述层来制造。这些不同层的性能和功能以及实例材料被更详细地描述在US7,279,704的6-10栏中，所述内容通过引用结合在本文中。
用于这些层中的每个层的更多实例是可获得的。例如，一种柔性和透明的基材-阳极组合被公开在美国专利5,844,363号中，该专利的全部内容通过引用结合在本文中。p-掺杂的空穴传输层的一个例子是按照50:1的摩尔比率掺杂了F4-TCNQ的m-MTDATA，如在美国专利申请出版物2003/0230980中所公开的，该文献的全部内容通过引用结合在本文中。发射和主体材料的实例被公开在Thompson等人的美国专利6,303,238号中，该专利的全部内容通过引用结合在本文中。n-掺杂的电子传输层的一个例子是按照1:1的摩尔比率掺杂了Li的BPhen，如在美国专利申请出版物2003/0230980号中所公开的，该文献的全部内容通过引用结合在本文中。美国专利5,703,436号和5,707,745号(它们的全部内容通过引用结合在本文中)公开了包括复合阴极在内的阴极的例子，所述复合阴极具有金属如Mg:Ag的薄层，在所述金属薄层上具有层叠的透明的、导电的、溅射沉积的ITO层。封闭层的理论和使用更详细地描述在美国专利6,097,147和美国专利申请出版物2003/0230980号中，它们的全部内容通过引用结合在本文中。在美国专利申请出版物2004/0174116中提供了注入层的实例，所述文献的全部内容通过引用结合在本文中。对保护层的描述可以在美国专利申请出版物2004/0174116中找到，它的全部内容通过引用结合在本文中。“增进层”在器件中与上述封闭层占相同的位置,并且可以具有封闭功能或改进器件性能的其它功能。
图2显示了颠倒的OLED200。该器件包括基材210，阴极215，发射层220，空穴传输层225，和阳极230。器件200可以通过按照顺序沉积所述层来制造。因为最常见的OLED构型具有布置在阳极上的阴极，并且器件200具有布置在阳极230下的阴极215，因此器件200可以被称为“颠倒的”OLED。与讨论器件100时所描述的那些材料类似的材料可用于器件200的相应层中。图2提供了如何从器件100的结构中省略掉一些层的一个实例。
在图1和2中示出的简单层状结构是作为非限制性例子提供的，并且可以理解，本发明的实施方案可以与各种其它结构相结合使用。所述的特定材料和结构是举例性质的，并且其它材料和结构可以被使用。功能化的OLED可以通过以不同的方式组合所述的各种层来实现，或者某些层可以被完全省略，基于设计、性能和成本因素。没有具体描述的其它层也可以被包括。可以使用除了具体描述的那些材料之外的材料。虽然在这里提供的许多实施例将各种层描述为包括单一一种材料，但是可以理解，可以使用材料的组合，如主体和掺杂剂的混合物，或更一般地混合物。还有，这些层可具有各种亚层。在这里给予各种层的名称并不是意图严格限制的。例如，在器件200中，空穴传输层225传输空穴并将空穴注入到发射层220中，因此可以被描述为空穴传输层或空穴注入层。在一个实施方案中，OLED可以被描述为具有设置在阴极和阳极之间的“有机层”。该有机层可以包括单个层，或者可以进一步包括例如讨论图1和2时所述的不同有机材料的多个层。
没有具体描述的结构和材料也可以使用，例如由聚合物材料组成的OLED(PLED)，如公开在美国专利5,247,190(Friend等人)中的PLED，该专利的全部内容通过引用结合在本文中。作为另一个例子，可以使用具有单个有机层的OLED。OLED可以堆叠，例如如在美国专利5,707,745(Forrest等人)中所述，该专利的全部内容通过引用结合在本文中。OLED结构可以背离在图1和2中图示说明的简单层状结构。例如，基材可以包括有角度的反射面以改进外偶联，如在Forrest等人的美国专利6,091,195中所述的台式结构，和/或在Bulovic等人的美国专利5,834,893中描述的坑形结构，所述专利的全部内容通过引用结合在本文中。
除非另作说明，各种实施方案的这些层中的任何一层可以通过任何合适的方法沉积。对于有机层，优选的方法包括热蒸发，墨喷(如在美国专利6,013,982和6,087,196中所述的，所述专利的全部内容通过引用结合在本文中)，有机气相沉积(OVPD)(如在Forrest等人的美国专利6,337,102中所述的，该专利的全部内容通过引用结合在本文中)，和通过有机蒸气喷印(OVJP)的沉积(如在美国专利申请序列号10/233,470中所述的，该专利申请的全部内容通过引用结合在本文中)。其它合适的沉积方法包括旋涂和其它溶液型工艺。溶液型工艺优选在氮或惰性气氛中进行。对于其它层，优选的方法包括热蒸发。优选的图案化方法包括通过掩模的沉积，冷焊(如在美国专利6,294,398和6,468,819中描述的方法，所述专利的全部内容通过引用结合在本文中)，和与某些沉积方法如墨喷和OVJD联合的图案化。其它方法也可以使用。被沉积的材料可以被改性，以使得它们与具体的沉积方法相容。例如，取代基如支化或未支化的并优选含有至少3个碳的烷基和芳基可以用于小分子中，以提高它们经历溶液加工的能力。可以使用具有20个碳或更多个碳的取代基，而3-20个碳是优选的范围。具有不对称结构的材料可以比具有对称结构的那些材料有更好的溶液加工性，因为不对称材料可以有更低的重结晶倾向。树状分子取代基可用来提高小分子经历溶液加工的能力。
根据本发明的实施方案制造的器件可以结合到各种各样的消费产品中，包括平板显示器，计算机显示器，电视，广告牌，内部或外部照明和/或发信号的光源，平视显示器(headsupdisplay)，全透明显示器，柔性显示器，激光打印机，电话，移动电话，个人数字助理(PDA)，膝上型计算机，数字式摄象机，摄像放像机，取景器，微型显示器，车辆，大面积幕墙，戏院或露天运动场屏幕，或标牌。各种控制机构可用来控制根据本发明制造的器件，包括无源矩阵和有源矩阵。许多的器件预计在人感觉舒适的温度范围如18℃到30℃的范围中使用，更优选在室温(20-25℃)使用。
在这里描述的材料和结构可以应用在不同于OLED的器件中。例如，其它光电器件如有机太阳能电池和有机光检测器可以使用所述材料和结构。更一般地，有机器件如有机晶体管可以使用所述材料和结构。
术语卤、卤素、烷基、环烷基、烯基、炔基、芳烷基、杂环基、芳基和杂芳基是本领域已知的,并且被在US7,279,704的31-32栏中定义，所述定义通过引用结合在本文中。
本发明提供了化合物，所述化合物包含含苯并[9,10]菲的苯并稠合的噻吩。苯并[9,10]菲是具有高三重态能量，但还具有高的π-共轭和相对小的第一单线态和第一三重态能级间能量差的聚芳族烃。这将预示，与具有类似三重态能量的其它芳族化合物(例如联苯)相比，苯并[9,10]菲具有相当容易被利用的HOMO和LUMO能级。使用苯并[9,10]菲和其衍生物作为主体的优点在于，它能够容纳红、绿和甚至蓝色磷光掺杂剂以给出高的效率，而没有能量猝灭。苯并[9,10]菲主体可以被用于提供高效和稳定的PHOLED。参见KwongandAlleyene,TriphenyleneHostsinPhosphorescentLightEmittingDiodes,2006,60pp,US2006/0280965A1。苯并稠合的噻吩可以被用作空穴传输有机介质。另外，苯并噻吩类，即二苯并[b,d]噻吩(在本文中称为“二苯并噻吩”)，苯并[b]噻吩和苯并[c]噻吩的三重态能量是相当高的。苯并稠合的噻吩和苯并[9,10]菲的组合作为PHOLED中的主体可能是有益的。更具体地说，苯并稠合的噻吩通常更倾向于传输空穴而不是传输电子,而苯并[9,10]菲更倾向于传输电子而不是传输空穴。因此，在一个分子中组合这两个结构部分可以提供改进的电荷平衡，这可以改善器件的寿命、效率和低电压性能。所述两个结构部分的不同化学连接可以被用于调节所得到的化合物的性能，以使得该化合物最适合特定的磷光发射体、器件结构和/或制造方法。例如，间亚苯基连接预期导致较高的三重态能量和较高的溶解性，而对亚苯基连接预期导致较低的三重态能量和较低的溶解性。
类似于对苯并稠合的噻吩的描述，苯并稠合的呋喃也通常是具有相当高三重态能量的空穴传输材料。苯并稠合的呋喃的实例包括苯并呋喃和二苯并呋喃。因此，含苯并[9,10]菲和苯并呋喃二者的材料可以被有利地用作PHOLED中的主体或空穴封闭材料。含这两个基团二者的化合物可以提供改善的电子稳定作用，这可以改善器件稳定性和效率，同时具有低电压。通过使用不同的化学连接来连接所述苯并[9,10]菲和所述苯并呋喃，所述含苯并[9,10]菲的苯并呋喃化合物的性能可以根据需要调节。
所述化合物可以用不必是苯并[9,10]菲、苯并稠合的噻吩和苯并稠合的呋喃的基团取代。优选地，用作所述化合物的取代基的任何基团具有足够高的三重态能量以维持具有苯并[9,10]菲的苯并稠合的噻吩或苯并稠合的呋喃的益处(即，所述取代基的三重态能量维持苯并稠合的噻吩、苯并稠合的呋喃和苯并[9,10]菲的高三重态能量)。可以用作所述化合物的取代基的这样的基团的实例可以包括选自CnH2n+1，OCnH2n+1，OAr1，N(CnH2n+1)2，N(Ar1)(Ar2)，CH＝CH-CnH2n+1，C≡CHCnH2n+1，Ar1，Ar1-Ar2，CnH2n-Ar1或无取代的任何取代基，其中n是1，2，3，4，5，6，7，8，9或10,和其中Ar1和Ar2独立地选自苯、联苯、萘、苯并[9,10]菲、咔唑和它们的杂芳族类似物。本文中描述的所述化合物具有适合用在具有磷光性蓝色发射材料的器件的足够高的三重态能量。
本文中描述的所述化合物的取代基是非稠合的，使得所述取代基不稠合到所述化合物的苯并[9,10]菲、苯并稠合的呋喃或苯并稠合的噻吩结构部分上。所述取代基任选地可以互相稠合(即彼此稠合)。
本文中提供的材料除了提供改进的器件稳定性和效率外，当器件通过气相沉积和溶液加工方法制造时，本文中提供的材料还可以提供改进的器件中膜形成。特别地，提供改进的制造的材料具有中间吡啶环，所述苯并稠合的噻吩和苯并[9,10]菲(或苯并呋喃和苯并[9,10]菲)连接到所述中间吡啶环上。所述改进的膜形成据信是由于所述化合物中极性和非极性环的组合导致的。
含苯并[9,10]菲的苯并稠合的噻吩的实例包括具有式(I)、式(II)和式(III)的结构的化合物:
R1、R2和R3独立地选自烷基、烷氧基、氨基、烯基、炔基、芳烷基、芳基、杂芳基和氢。R1、R2和R3各自可以表示多个取代基。R1、R2和R3中至少一个包括苯并[9,10]菲基团。所述苯并[9,10]菲基团可以直接连接在式(I)、(II)或(III)的结构上，但是在所述苯并[9,10]菲基团和所述式(I)、(II)或(III)的结构之间可以有“间隔基”。
含苯并[9,10]菲的苯并稠合的噻吩或苯并稠合的呋喃的实例包括具有以下结构的化合物:
X是S或O。优选地，R1、R2和R3是非稠合的取代基，所述取代基独立地选自CnH2n+1，OCnH2n+1，OAr1，N(CnH2n+1)2，N(Ar1)(Ar2)，CH＝CH-CnH2n+1，C≡CHCnH2n+1，Ar1，Ar1-Ar2，CnH2n-Ar1，或无取代。R1、R2和R3各自可以表示单、二、三或四取代。n是1，2，3，4，5，6，7，8，9或10。Ar1和Ar2独立地选自苯、联苯、萘、苯并[9,10]菲、咔唑和它们的杂芳族类似物。R1、R2和R3中至少一个包括苯并[9,10]菲基团。
具有式(I)的结构的化合物的实例包括:
R1－Rn独立地表示单、二、三或四取代，其选自烷基、烷氧基、氨基、烯基、炔基、芳烷基、芳基和杂芳基，或无取代。
具有式(IV)的结构的化合物的实例包括:
X是S或O。优选地，X是S。R1－Rn独立地选自CnH2n+1，OCnH2n+1，OAr1，N(CnH2n+1)2，N(Ar1)(Ar2)，CH＝CH-CnH2n+1，C≡CHCnH2n+1，Ar1，Ar1-Ar2，CnH2n-Ar1，或无取代。R1－Rn各自可以表示单、二、三或四取代。n是1，2，3，4，5，6，7，8，9或10。Ar1和Ar2独立地选自苯、联苯、萘、苯并[9,10]菲、咔唑和它们的杂芳族类似物。R1、R2和R3中至少一个包括苯并[9,10]菲基团。
具有式(II)的结构的化合物的实例包括:
R1－Rn独立地表示单、二、三或四取代，其选自烷基、烷氧基、氨基、烯基、炔基、芳烷基、芳基和杂芳基，或无取代。
具有式(V)的结构的化合物的实例包括:
X是S或O。优选地，X是S。R1－Rn独立地选自CnH2n+1，OCnH2n+1，OAr1，N(CnH2n+1)2，N(Ar1)(Ar2)，CH＝CH-CnH2n+1，C≡CHCnH2n+1，Ar1，Ar1-Ar2，CnH2n-Ar1，或无取代。R1－Rn各自可以表示单、二、三或四取代。n是1，2，3，4，5，6，7，8，9或10。Ar1和Ar2独立地选自苯、联苯、萘、苯并[9,10]菲、咔唑和它们的杂芳族类似物。R1、R2和R3中至少一个包括苯并[9,10]菲基团。
具有式(III)的结构的化合物的实例包括:
R1－Rn独立地表示单、二、三或四取代，其选自烷基、烷氧基、氨基、烯基、炔基、芳烷基、芳基和杂芳基，或无取代。
具有式(VI)的结构的化合物的实例包括:
X是S或O。优选地，X是S。R1－Rn独立地选自CnH2n+1，OCnH2n+1，OAr1，N(CnH2n+1)2，N(Ar1)(Ar2)，CH＝CH-CnH2n+1，C≡CHCnH2n+1，Ar1，Ar1-Ar2，CnH2n-Ar1，或无取代。R1－Rn各自可以表示单、二、三或四取代。n是1，2，3，4，5，6，7，8，9或10。Ar1和Ar2独立地选自苯、联苯、萘、苯并[9,10]菲、咔唑和它们的杂芳族类似物。R1、R2,和R3中至少一个包括苯并[9,10]菲基团。
上面公开的每种含苯并[9,10]菲的苯并稠合的噻吩都可以有利地用在有机发光器件中。所述化合物特别可用作有机发光器件的发射层中的主体，这样的器件中的增进层材料，或二者。
实验
化合物实施例
实施例14-(苯并[9,10]菲-2-基)二苯并噻吩(化合物1S)
1.2-溴代苯并[9,10]菲的合成
上述化合物的合成被描述在US20060280965中。
2.4-(苯并[9,10]菲-2-基)二苯并噻吩的合成
将4.4g(14.6mmol)2-溴代苯并[9,10]菲，4.0g(17.5mmol)4-二苯并噻吩硼酸，0.51g(0.44mmol)四(三苯基膦)合钯和4.0g(43.4mmol)碳酸钾加入到含有溶剂90mL甲苯和10mL水的250mL圆底烧瓶中。将反应混合物用氮气吹扫30分钟，并且然后将其在氮气氛下在搅拌的同时加热回流过夜。冷却反应混合物，并且将有机萃取物通过柱层析和使用甲苯的重结晶纯化。得到5.1g(86％)白色固体产物，该产物通过1HNMR证实。
实施例24-(3-(苯并[9,10]菲-2-基)苯基)二苯并噻吩(化合物2S)
1.三氟甲磺酸3-(2-苯并[9,10]菲)苯基酯的合成
上述化合物的合成被描述在临时申请序列号60/963,944中。
2.4-(3-(苯并[9,10]菲-2-基)苯基)二苯并噻吩的合成
将4.52g(10.0mmol)三氟甲磺酸3-(苯并[9,10]菲-2-基)苯基酯，3.0g(13.0mmol)4-二苯并噻吩硼酸，0.46g(0.5mmol)Pd2(dba)3，0.82g(2.0mmol)2-二环己基膦酰基-2’,6’-二甲氧基联苯，12.7g(60.0mmol)K3PO4以及150mL甲苯和15mL水加入到一个250mL圆底烧瓶中。将反应混合物在氮气氛下加热回流过夜。冷却反应混合物，并且将有机萃取物通过柱层析和重结晶纯化。得到4.3g(88％)白色固体产物，该产物通过1HNMR证实。
实施例32,8-二(苯并[9,10]菲-2-基)二苯并噻吩(化合物5S)
1.4,4,5,5-四甲基-2-(苯并[9,10]菲-2-基)-1,3,2-二氧杂硼杂戊烷的合成
该化合物的合成被描述在US2006/0280965中。
1.2,8-二(苯并[9,10]菲-2-基)二苯并噻吩的合成
将2.25g(6.3mmol)4,4,5,5-四甲基-2-(苯并[9,10]菲-2-基)-1,3,2-二氧杂硼杂戊烷，0.92g(2.7mmol)2,8-二溴代二苯并噻吩，0.12g(0.14mmol)Pd2(dba)3，0.22g(0.53mmol)2-二环己基膦酰基-2′，6′-二甲氧基联苯，3.4g(16.0mmol)K3PO4，100mL甲苯和10mL水加入到一个250mL的圆底烧瓶中。将反应混合物用氮气吹扫20分钟，然后在搅拌下加热回流过夜。将反应混合物冷却和过滤。将白色固体用甲醇洗涤3次(3x100mL)和用二氯甲烷洗涤(2x100mL)。得到1.6g固体产物(94％收率)，该产物通过用甲苯重结晶和升华进一步纯化。所述产物由固体探针MS证实。
实施例4化合物20S
1.2-溴代二苯并噻吩的合成
将15g(79.9mmol)二苯并噻吩溶解在1.5升氯仿中。向该溶液中滴加12.76g(79.9mmol)溴。将反应混合物在室温下剧烈搅拌2天，然后用亚硫酸钠水溶液处理。将有机相蒸发，给出白色固体，其具有48％未反应的二苯并噻吩，50％2-溴代二苯并噻吩和约小于2％2,8-二溴代二苯并噻吩，基于GC-MS和HPLC结果。将该混合物用乙酸乙酯反复重结晶，得到纯的2-溴代二苯并噻吩。
2.硼酯产物的合成
将8g(17.5mmol)三氟甲磺酸3-(2-苯并[9,10]菲)苯基酯，9.1g(35.2mmol)双(频哪醇根)二硼(bis(pinacolato)diboron)，290mg(0.35mmol)Pd(dffp)2Cl2，5.2g(52.5mmol)KOAc和150mL无水二噁烷加入到一个250mL的三口烧瓶中。将反应混合物在氮气氛下加热至90℃维持20小时。在柱层析后得到7.0g白色固体，所述柱层析使用在己烷中的30％乙酸乙酯作为洗脱剂。产物由1HNMR证实。
3.化合物20S的合成
将2g(7.1mmol)2-溴代二苯并噻吩，4.0g(9.3mmol)步骤2中的硼酯产物，325mg(0.355mmol)Pd2(dba)3，582g(1.4mmol)S-phose，9g(42mmol)K3PO4，90mL甲苯和10mL水加入到一个250mL烧瓶中。将反应混合物在氮气氛下加热回流过夜。将反应混合物用二氯甲烷萃取，并且有机萃取物通过硅胶柱层析和重结晶纯化。得到约2.9g(85％)白色固体产物，该产物通过1HNMR证实。
实施例5化合物10S
1.4,4’-二甲氧基邻三联苯的合成
制备1,2-二溴代苯(50g，212mmol)，4-甲氧基苯基硼酸(78g，513mmol)，三苯基膦(11.12g，42.2mmol)，碳酸钾(73.25g，530mmol)，二甲氧基乙烷(290mL)和水(290mL)的混合物。将氮气直接鼓泡到所述混合物中20分钟。添加乙酸钯(4.76g，21.2mmol)，并且将所述混合物在氮气氛下加热回流过夜。冷却所述反应混合物，并且添加水和二氯甲烷。分离各层，并且水层用二氯甲烷萃取。合并的有机层通过塞力特硅藻土过滤，并且用盐水洗涤，用硫酸镁干燥，过滤，蒸发，得到黑色油状物。将所述粗材料通过柱层析纯化，使用在己烷中的0梯度变化至100％的二氯甲烷洗脱剂洗脱。将主要的级分通过使用Kugelrohr在200－220℃进行的蒸馏纯化。得到49g(80％)纯净的产物。
2.2,11-二甲氧基苯并[9,10]菲的合成
将12.4g(42.7mmol)4,4’-二甲氧基-邻三联苯和16g(63.0mmol)碘屑放置在一个250mL的反应容器中。添加200mL甲苯，接着添加30mL环氧丙烷。向所述光反应器提供一个通过循环冷却剂冷却的冷凝器。使用400W中压汞灯作为光源。将所述反应容器放在通风橱中。打开所述灯，并且设定冷却剂的温度使得离开所述反应器的水维持在20℃和25℃之间(通过连接到出口物流的热电偶监测)。使所述反应持续18小时。过滤出固体并用己烷洗涤，仅回收2.2g材料。将滤液用甲苯稀释并用硫酸钠溶液洗涤。水层用甲苯反萃取，并且有机层用硫酸镁干燥，过滤，和蒸发。将材料溶解在甲苯中，并添加亚硫酸钠溶液和搅拌。分离各层，水层用甲苯萃取，并且合并的有机层用硫酸镁干燥，过滤，和蒸发。残余物通过柱层析纯化，使用0-100％乙酸乙酯/己烷洗脱。得到8.8g材料(72％)。
3.苯并[9,10]菲-2,11-二酚的合成
将2,11-二甲氧基苯并[9,10]菲(8.8g，30.5mmol)和吡啶盐酸盐(31.73g，274.6mmol)的混合物加热到220℃，维持2小时。冷却所述混合物并添加水。过滤出产生的固体物，用水洗涤，和在高真空下干燥。得到7.45g(94％)期望的产物。
4.苯并[9,10]菲-2,11-二基双(三氟甲磺酸酯)的合成
将苯并[9,10]菲-2,11-二酚(7.45g，28.62mmol)加到100mL二氯甲烷和13mL吡啶中，并且将所述溶液在冰盐浴中冷却。在氮气氛下向所述溶液中滴加三氟甲磺酸酐(19mL，114.49mmol)在70mL二氯甲烷中的溶液。允许所述反应进行2小时，并且通过添加甲醇和水来猝灭该反应，接着用二氯甲烷稀释。过滤出棕褐色固体物，并用二氯甲烷和水洗涤。分离在滤液中的各层，并且水层用二氯甲烷萃取。将有机萃取液用硫酸镁干燥，过滤，和蒸发，得到棕色固体物。所述棕色固体物通过柱层析纯化，用0－100％二氯甲烷/己烷洗脱，然后在170℃升华，和然后从300mL沸腾甲苯中重结晶两次。得到11.4g产物(76％)。
5.化合物10S的合成
制备苯并[9,10]菲-2,11-二基双(三氟甲磺酸酯)(1.5g，2.9mmol)，二苯并噻吩-4-硼酸(2.6g，11.4mmol)，氟化钾(1.1g，19mmol)和THF50mL的混合物。将氮气直接鼓泡到所述混合物中1小时。然后添加乙酸钾(13mg，0.06mmol)和三环己基膦(19mg，0.07mmol),并且然后再将氮气鼓泡到所述混合物中30分钟。将所述混合物在50℃加热过夜。然后将反应冷却到室温。通过过滤收集沉淀物。将白色固体物放在一个索格利特萃取器中，并且通过回流THF过夜来洗涤。收集在所述萃取器中的固体物，给出0.9克白色固体(收率53％)。
实施例6化合物9S
1.2-(3'-甲氧基联苯-3-基)苯并[9,10]菲的合成
将12.9g(28.5mmol)三氟甲磺酸3-(苯并[9,10]菲-2-基)苯基酯，6.5g(42.8mmol)3-甲氧基苯基硼酸，0.47g(1.1mmol)2-二环己基膦酰基-2’,6’-二甲氧基联苯(SPhos)和18.2g(85.5mmol)磷酸三钾(K3PO4)称量到一个圆底烧瓶中。向所述烧瓶中添加150mL甲苯和80mL水作为溶剂。用氮气吹扫所述溶液，并且添加0.26g(0.28mmol)三(二亚苄基丙酮)二钯(0)[Pd2(dba)3]。将所述溶液加热至回流，维持12小时。在冷却后，分离有机层并用硫酸镁干燥。所述产物通过使用己烷/二氯甲烷作为洗脱剂(1/0梯度变化至3/2)的柱层析容易地分离。通过旋转蒸发除去溶剂，得到11.7g(28mmol)产物2-(3'-甲氧基联苯-3-基)苯并[9,10]菲。
2.3'-(苯并[9,10]菲-2-基)联苯-3-酚的合成
在一个圆底烧瓶中，在氮气氛下，将11.5g(28mmol)2-(3'-甲氧基联苯-3-基)苯并[9,10]菲和21.1g(183mmol)吡啶盐酸盐加热到204℃。在冷却后，添加水并用二氯甲烷萃取。合并的有机部分用另外的水洗涤，并且通过旋转蒸发除去溶剂。将固体物干填充在塞力特硅藻土上，并且通过柱层析纯化所述产物，使用己烷:二氯甲烷(1:4)作为洗脱剂。通过旋转蒸发除去溶剂，得到8.6g(22mmol)产物3'-(苯并[9,10]菲-2-基)联苯-3-酚。
3.三氟甲磺酸3'-(苯并[9,10]菲-2-基)联苯-3-基酯的合成
在氮气氛下，将8.6g(22mmol)3'-(苯并[9,10]菲-2-基)联苯-3-酚添加到含3.4g(43.4mmol)无水吡啶和450mL无水二氯甲烷的烧瓶中。将所述溶液在冰浴中冷却，并通过注射器缓慢添加12.2g(43.4mmol)三氟甲磺酸酐(Tf2O)。将所述溶液温热至室温并搅拌过夜。将所述溶液用水洗涤，用硫酸镁干燥，并且通过旋转蒸发除去溶剂。产物三氟甲磺酸3'-(苯并[9,10]菲-2-基)联苯-3-基酯通过柱层析纯化，使用己烷/二氯甲烷作为洗脱剂(1/0梯度变化至1/1)，得到10.7g(20.2mmol)。
4.化合物9S的合成
将5.5g(10.4mmol)上述步骤3的产物，3.0g(13.5mmol)4-硼酸二苯并噻吩，458mg(0.5mmol)Pd2(dba)3，820mg(2mmol)S-phose，12.7g(60mmol)磷酸钾和150mL甲苯加入到一个250烧瓶中。将反应混合物在氮气氛下加热回流过夜。然后将其冷却和后处理。在硅胶柱层析(使用在己烷中的20％二氯甲烷作为洗脱剂)和然后用甲醇洗涤后得到约5g白色产物。产物由1HNMR证实。
实施例7化合物19S
1.3,3’-二甲氧基-邻三联苯的合成
在一个装有搅拌棒、回流冷凝器和氮气入口的2000mL圆底烧瓶中，将1,2-二溴代苯(50.0g，0.212mol)，3-甲氧基苯基硼酸(77.3g，0.509mol)，乙酸钯(1.2g，5.33mmol)，三苯基膦(21.4mmol)，碳酸钠(78.9g，0.744mol)与二甲氧基乙烷(430mL)和水(290mL)合并，并且将它们加热回流4天。添加乙酸乙酯(500mL)，并且分离有机层，将其用硫酸镁干燥和蒸发至干，得到61.3g(99.7％)3,3’-二甲氧基-邻三联苯白色固体。
2.2,9-二甲氧基苯并[9,10]菲的合成
在一个装有氮气入口和搅拌棒的2000mL圆底烧瓶中，将3,3’-二甲氧基-邻三联苯(61.3g，0.211mol)溶解在无水二氯甲烷(1000mL)中。然后添加氯化铁(III)(68.6g，0.423mol),并且将所述混合物搅拌过夜。在第二天早晨，添加另外的2当量氯化铁(III),并且在1小时内反应完全。向所述混合物中添加甲醇和水，并且分离有机层，用硫酸镁干燥和蒸发至干。粗产物通过硅胶柱层析纯化，使用60/40二氯甲烷/己烷作为洗脱剂，给出50.7g浅黄色固体。将该固体从700mL乙腈中重结晶，得到49.1g2,9-二甲氧基苯并[9,10]菲。
3.2,9-二羟基苯并[9,10]菲的合成
将2,9-二甲氧基苯并[9,10]菲(49.1g，0.170mol)和吡啶盐酸盐(200g，1.70mol)放在一个装有搅拌棒、回流冷凝器和氮气入口的500mL圆底烧瓶中，并在220℃加热90分钟。冷却该溶液，并且添加水，导致形成白色沉淀物。通过真空过滤收集该白色沉淀物，用水洗涤和真空干燥，得到43.7g(96％)2,9-二羟基苯并[9,10]菲。
4.苯并[9,10]菲-2,7-二基双(三氟甲磺酸酯)的合成
向在装有搅拌棒和氮气入口的1000mL圆底烧瓶中的2,9-二羟基苯并[9,10]菲(17.5g，65mmol)和吡啶(300mL)的冷溶液(0℃)中滴加三氟甲磺酸酐(38.7g，137mmol)。将反应混合物在室温搅拌过夜。在蒸发掉吡啶后，将得到的固体与甲醇(500mL)在一起搅拌，并且通过真空过滤收集，给出32g白色粉末。将该白色粉末从500mL庚烷/二氯乙烷的30/70混合物中重结晶，得到28.3g(82％)2,9-双(三氟甲磺酰基)苯并[9,10]菲。
5.化合物19S的合成
制备苯并[9,10]菲-2,7-二基双(三氟甲磺酸酯)(2g，3.8mmol)，二苯并噻吩-4-硼酸(3.5g，15mmol)，氟化钾(1.5g，25mmol)和THF100mL的混合物。将氮气直接鼓泡到所述混合物中1小时。然后添加乙酸钾(17mg，0.08mmol)和三环己基膦(26mg，0.09mmol)，并且然后再将氮气鼓泡到所述混合物中30分钟。将该混合物在室温搅拌2天。然后将反应冷却到室温。通过过滤收集沉淀物。添加乙酸钾(17mg，0.08mmol)和三环己基膦(26mg，0.09mmol)，然后再将氮气鼓泡到所述混合物中15分钟。将该混合物在室温再搅拌2天。将灰色固体物放在一个索格利特萃取器中，并且通过回流THF过夜来洗涤。收集在所述萃取器中的固体物，给出2.1克白色固体(收率92％)。
实施例8化合物22S
步骤1
制备2,6-二氯吡啶(13g，88mmol)，二苯并噻吩-4-硼酸(5g，22mmol)，磷酸三钾(28g，132mmol)，甲苯300mL和水30mL的混合物。将氮气直接鼓泡到所述混合物中1小时。然后添加三(二亚苄基丙酮)(0.54g，1.3mmol),并且然后将氮气再鼓泡到该混合物中20分钟。将所述混合物在室温下搅拌2天。然后收集有机层，并且水层用二氯甲烷萃取。合并的有机层用硫酸镁干燥和浓缩。粗产物通过硅胶快速层析纯化，使用最高达10％乙酸乙酯/己烷洗脱，给出5克黄色固体物。将该黄色固体物进一步从二氯乙烷/庚烷中重结晶，得到2.5克白色固体物(39％)。
2.化合物22S的合成
制备4,4,5,5-四甲基-2-(苯并[9,10]菲-2-基)-1,3,2-二氧杂硼杂戊烷(2.2g，6.1mmol)，2-氯-6-(二苯并噻吩-4-基)吡啶(1.5g，5.1mmol)，磷酸三钾(3.3g，15.3mmol)，甲苯150mL和水15mL的混合物。将氮气直接鼓泡到所述混合物中40分钟。然后添加三(二亚苄基丙酮)二钯(56mg，0.06mmol)和双(环己基)-2-联苯基膦(100mg，0.24mmol),并且然后再将氮气鼓泡到所述混合物中17分钟。将反应混合物在氮气氛下回流过夜。通过过滤收集沉淀物，并且用甲苯、二氯甲烷和甲醇洗涤。然后，将所述产物溶解在250mL沸腾二甲苯中，过滤通过一个小的硫酸镁柱。将滤液加热至回流以溶解所有的固体，并且允许其慢慢冷却下来。得到重结晶过的产物，为2.3克白色固体(93％)。
实施例9化合物21S
1.2-氯-6-(3-甲氧基苯基)吡啶的合成
制备间甲氧基苯基硼酸(10g，65.8mmol)，2,6-二氯吡啶(9.7g，65.8mmol)，碳酸钾(27.3g，197.4mmol)，三苯基膦(2.07g，7.9mmol)，二甲氧基乙烷250mL和水80mL的混合物。将氮气直接鼓泡到所述混合物中20分钟。然后添加乙酸钯(0.44g，2.0mmol)。将氮气再鼓泡到所述混合物中10分钟。将所述混合物在氮气氛下加热回流过夜。将反应混合物冷却到室温。分离有机层，并且水层用二氯甲烷萃取。合并的有机层用硫酸镁干燥，过滤和蒸发。将混合物通过硅胶柱纯化，使用最高达10％乙酸乙酯/己烷洗脱，得到6.5g无色油状物(45％)。
2.2-(二苯并[b,d]噻吩-4-基)-6-(3-甲氧基苯基)吡啶的合成
制备2-氯-6-(3-甲氧基苯基)吡啶(3.5g，16mmol)，二苯并噻吩-4-硼酸(4g，17.5mmol)，磷酸钾(10.2g，48mmol)，二甲氧基乙烷500mL和水50mL的混合物。将氮气直接鼓泡到所述混合物中15分钟。然后添加三(二亚苄基丙酮)二钯(147mg，0.16mmol)和2-二环己基膦酰基-2',6'-二甲氧基联苯(263mg，0.64mmol)，并且然后再将氮气鼓泡到所述混合物中15分钟。将反应混合物在氮气氛下加热回流过夜。在第二天，将反应混合物冷却到室温。分离有机层，并且水层用二氯甲烷萃取。合并的有机层用硫酸镁干燥，过滤和蒸发。将混合物通过硅胶柱纯化，使用最高达10％乙酸乙酯/己烷洗脱，得到3.8g黄色固体(65％)。
3.3-(6-(二苯并[b,d]噻吩-4-基)吡啶-2-基)苯酚的合成
将2-(二苯并[b,d]噻吩-4-基)-6-(3-甲氧基苯基)吡啶(3.8g，10.3mmol)溶解在120mL二氯甲烷中。将该溶液在氮气氛下冷却到0℃。在0℃向该溶液中慢慢添加BBr3(22.8mL，1M的己烷溶液)，然后将该溶液缓慢升温至室温。将该混合物在室温下搅拌过夜。观察到形成了棕色固体物。通过缓慢添加100mL水猝灭该反应。通过旋转蒸发除去二氯甲烷。然后将该混合物回流3小时。添加饱和碳酸氢钠溶液以中和该混合物，然后将该混合物用二氯甲烷和乙酸乙酯萃取。合并的有机层用硫酸镁干燥，过滤和在减压下浓缩，得到4克玻璃状茶褐色固体。该产物直接用于后面的步骤而不用进一步纯化。
4.三氟甲磺酸3-(6-(二苯并[b,d]噻吩-4-基)吡啶-2-基)苯基酯的合成
将3-(6-(二苯并[b,d]噻吩-4-基)吡啶-2-基)苯酚(4g，11.3mmol)悬浮在100mL吡啶中，用丙酮/冰浴冷却至-10℃。在氮气氛下缓慢添加三氟甲磺酸酐(2.29mL，13.6mmol)。将该混合物在0℃搅拌2小时，然后倾倒入200mL饱和碳酸氢钠溶液中。将该混合物用乙酸乙酯萃取。合并的有机层用硫酸镁干燥，过滤和蒸发。混合物通过硅胶柱纯化两次，使用最高达15％乙酸乙酯/己烷洗脱。然后，通过添加己烷使产物从其二氯甲烷溶液中沉淀出来，得到1.8克白色固体(最后两步的总收率为36％)。
5.化合物21S的合成
制备三氟甲磺酸3-(6-(二苯并[b,d]噻吩-4-基)吡啶-2-基)苯基酯(1.65g，3.4mmol)，4,4,5,5-四甲基-2-(苯并[9,10]菲-2-基)-1,3,2-二氧杂硼杂戊烷(1.32g，3.7mmol)，磷酸钾(2.16g，10.2mmol)，甲苯100mL和水10mL的混合物。将氮气直接鼓泡到所述混合物中25分钟。然后添加三(二亚苄基丙酮)二钯(31mg，0.034mmol)和2-二环己基膦酰基-2',6'-二甲氧基联苯(55mg，0.14mmol)，并且然后再将氮气鼓泡到所述混合物中15分钟。将反应混合物在氮气氛下加热回流8小时。在第二天，将反应混合物冷却到室温。通过过滤收集残余物，用甲苯、二氯甲烷和甲醇充分洗涤，得到1.8克灰色固体。在用于器件制造前，将该灰色固体在260℃升华两次。
实施例10化合物4S
1.2,11-双(3-甲氧基苯基)苯并[9,10]菲的合成
制备苯并[9,10]菲-2,11-二基双(三氟甲磺酸酯)(2g，3.8mmol)，3-甲氧基苯基硼酸(2.3g，15mmol)，磷酸三钾(4.8g，23mmol)，甲苯100mL和水10mL的混合物。将氮气直接鼓泡到所述混合物中30分钟。然后添加三(二亚苄基丙酮)二钯(70mg，0.076mmol)和双(环己基)-2-联苯基膦(125mg，0.30mmol)，并且然后再将氮气鼓泡到所述混合物中15分钟。将反应在氮气氛下回流3小时。在冷却到室温后，收集反应混合物的有机层，用硫酸镁干燥，和在减压下浓缩。粗产物通过硅胶快速层析纯化，给出1.6g白色固体(收率95％)。
2.3,3'-(苯并[9,10]菲-2,11-二基)二苯酚的合成
将2,11-双(3-甲氧基苯基)苯并[9,10]菲(1.6g，3.7mmol)和吡啶盐酸盐(4.3g，37mmol)的混合物在氮气氛下在220℃加热2.5小时。将反应物冷却到室温，并且用水洗涤。通过过滤收集到1.6g棕色残余物，将其在真空下干燥，并且不用进一步纯化用于下一步骤。
3.3,3'-(苯并[9,10]菲-2,11-二基)双(3,1-亚苯基)双(三氟甲磺酸酯)的合成
将3,3'-(苯并[9,10]菲-2,11-二基)二苯酚(1.6g，3.9mmol)悬浮在50mL二氯甲烷和5mL吡啶的混合物中。将该混合物用冰/水浴冷却到0℃。将三氟甲磺酸酐(1.44mL，8.5mmol)溶解在30mL二氯甲烷中，并在氮气氛下在0℃缓慢添加到所述反应混合物中。然后将反应在室温在氮气氛下搅拌过夜。向反应中添加20mL甲醇。通过旋转蒸发浓缩所述混合物。将残余物悬浮在水中，然后通过过滤收集。在用水洗涤后，将残余物在真空下干燥。粗产物通过硅胶快速层析纯化，使用在己烷中的最高达30％二氯甲烷洗脱，给出白色固体1.6克(最后两步的总收率:65％)。
4.化合物4S的合成
制备3,3'-(苯并[9,10]菲-2,11-二基)双(3,1-亚苯基)双(三氟甲磺酸酯)(1.6g，2.4mmol)，二苯并噻吩-4-硼酸(2.7g，12mmol)，磷酸三钾(3.4mmol，16mmol)，甲苯100mL和水50mL的混合物。将氮气直接鼓泡到所述混合物中1小时。然后添加三(二亚苄基丙酮)二钯(44mg，0.048mmol)和双(环己基)-2-联苯基膦(78mg，0.19mmol)，并且然后再将氮气鼓泡到所述混合物中30分钟。将反应回流过夜。在将反应冷却到室温后，通过过滤收集残余物，并且用甲醇和二氯甲烷洗涤，给出最终产物。
实施例11化合物23S
1.4-苯基二苯并噻吩的合成
将10g(41.6mmol)4-二苯并噻吩硼酸，6.25g(39.6mmol)溴代苯，366mg(0.39mmol)Pd2(dba)3，656mg(1.6mmol)S-phose，25.4g(120mmol)K3PO4，180mL甲苯和20mL水加入到一个500mL烧瓶中。将该混合物在氮气氛下加热回流过夜。反应混合物通过硅胶柱层析纯化，使用纯己烷作为洗脱剂。得到约8.5g(83％)白色固体产物，其由MS证实。
2.4-苯基二苯并噻吩-6-硼酸的合成
在一个250mL三口烧瓶中，将3.5g(13.4mmol)4-苯基二苯并噻吩溶解在约30mL无水THF中，并将其冷却到-78℃。向该混合物中添加17mL(27mmol)1.6M的BuLi在己烷中的溶液，并且搅拌30分钟。移开冷却浴，并且将反应保持搅拌过夜。将反应混合物再冷却到-78℃，添加4.5mL(40mmol)硼酸三甲酯，并在室温下搅拌4小时。添加约1001MHCl，并保持搅拌1小时。将混合物用乙酸乙酯萃取，并且合并有机萃取物。蒸干溶剂。将固体物添加到约100mL20％乙酸乙酯/己烷中，并搅拌数小时，然后过滤。将过滤出的固体用己烷洗涤数次。得到约2.5g白色固体产物，该产物由1HNMR证实。
3.化合物23S的合成
将2.4g(7.89mmol)上述硼酸，3.3g(7.2mmol)三氟甲磺酸3-(苯并[9,10]菲-2-基)苯基酯，67mg(0.08mmol)Pd2(dba)3，120mg(0.3mmol)S-phose，4.6g(21.7mmol)K3PO4，90mL甲苯和10mL水加入到一个250mL烧瓶中。将该混合物在氮气氛下加热回流6.5小时。用分液漏斗分离反应混合物，有机相通过使用在己烷中的20％二氯甲烷作为洗脱剂的硅胶柱层析和从甲苯-己烷混合物中重结晶来纯化。得到约3.8g(94％)白色固体产物，该产物通过1HNMR证实。
实施例12化合物24S
1.2,8-二苯基苯并噻吩的合成
将7.0g(20.4mmol)2,8-二溴代二苯并噻吩，6.4g(51.1mmol)苯基硼酸，187mg(0.2mmol)Pd2(dba)3，335mg(0.8mmol)S-phose，13g(61.2mmol)K3PO4，90mL甲苯和10mL水加入到一个250mL烧瓶中。将该混合物在氮气氛下加热回流4小时。用分液漏斗分离反应混合物，并且有机相通过硅胶柱层析纯化，使用在己烷中的20％二氯甲烷作为洗脱剂。得到约6.6g(96％)白色固体产物，该产物由GC-MS证实。
2.2,8-二苯基二苯并噻吩-4-硼酸的合成
在一个250mL三口烧瓶中，将3.8g(11.3mmol)2,8-二苯基苯并噻吩溶解在约30mL无水THF中。在-78℃，在氮气氛下，向该混合物中添加约18mL(28.3mmol)1.6M的BuLi在己烷中的溶液。将该混合物温热至室温并保持搅拌18小时。将反应混合物再冷却到-78℃，并且添加3.8mL(34mmol)硼酸三甲酯。在室温下搅拌该混合物4小时，然后添加约60mL1MHCl，同时搅拌1小时。用乙酸乙酯萃取该混合物，并且合并有机相。将溶剂蒸干。向固体中添加约100mL20％乙酸乙酯/己烷。搅拌数小时，然后过滤。将过滤出的固体用己烷洗涤3次。得到约2.2g白色固体产物，该产物由1HNMR证实。
3.化合物24S的合成
将2.0g(5.26mmol)2,8-二苯基二苯并噻吩-4-硼酸，2.18g(4.78mmol)三氟甲磺酸3-(苯并[9,10]菲-2-基)苯基酯，45mg(0.05mmol)Pd2(dba)3，80mg(0.19mmol)S-phose，3.2g(14mmol)K3PO4，90mL甲苯和10mL水加入到一个250mL烧瓶中。将该混合物在氮气氛下加热回流过夜。用分液漏斗分离反应混合物，并且有机相通过使用在己烷中的20％二氯甲烷作为洗脱剂的硅胶柱层析和从甲苯和己烷混合物中重结晶来纯化。得到约2.52g(84％)白色固体产物，该产物通过1HNMR证实。
实施例13化合物25S
1.2,8-二苯基苯并噻吩的合成
将7.0g(20.4mmol)2,8-二溴代二苯并噻吩，6.4g(51.1mmol)苯基硼酸，187mg(0.2mmol)Pd2(dba)3，335mg(0.8mmol)S-phose，13g(61.2mmol)K3PO4，90mL甲苯和10mL水加入到一个250mL烧瓶中。将该混合物在氮气氛下加热回流4小时。反应混合物用分液漏斗分离，并且有机相通过硅胶柱层析纯化，使用在己烷中的20％二氯甲烷作为洗脱剂。得到约6.6g(96％)白色固体产物，该产物由GC-MS证实。
2.2,8-二苯基二苯并噻吩-4-硼酸的合成
[UDC，请核实我们给上述中间体指定的名称]
在一个250mL三口烧瓶中，将3.8g(11.3mmol)2,8-二苯基苯并噻吩溶解在约30mL无水THF中。在-78℃，在氮气氛下，向该混合物中添加约18mL(28.3mmol)1.6M的BuLi在己烷中的溶液。将该混合物温热至室温并保持搅拌18小时。将反应混合物再冷却到-78℃，并且添加3.8mL(34mmol)硼酸三甲酯。在室温下搅拌该混合物4小时。然后添加约60mL1MHCl，同时继续搅拌1小时。用乙酸乙酯萃取该混合物，并且合并有机相。将溶剂蒸干。向固体中添加约100mL20％乙酸乙酯/己烷。搅拌数小时，然后过滤。将过滤出的固体用己烷洗涤。得到约2.2g白色固体产物，该产物由1HNMR证实。
3.2,4,8-三苯基苯并噻吩的合成
将5.5g(14.5mmol)2,8-二苯基二苯并噻吩-4-硼酸，2.3g(14.5mmol)溴代苯，135mg(0.15mmol)Pd2(dba)3，238mg(0.58mmol)S-phose，9.2g(43.2mmol)K3PO4，180mL甲苯和20mL水加入到一个500mL烧瓶中。将该混合物在氮气氛下加热回流过夜。反应混合物用分液漏斗分离，并且有机相通过硅胶柱层析纯化，使用在己烷中的20％乙酸乙酯作为洗脱剂。得到约5.1g2,4,8-三苯基苯并噻吩白色固体产物，该产物通过1HNMR证实。
4.2,4,8-三苯基二苯并噻吩-6-硼酸的合成
在一个250mL三口烧瓶中，将5.0g(12.13mmol)2,4,8-三苯基苯并噻吩溶解在约100mL无水THF中。在-78℃，在氮气氛下，向该混合物中添加约19mL(30.3mmol)1.6M的BuLi在己烷中的溶液。将该混合物温热至室温并保持搅拌18小时。将反应混合物再冷却到-78℃，并且添加3.8mL(34mmol)硼酸三甲酯。在室温下搅拌该混合物4小时，然后添加约100mL1MHCl，同时搅拌1.5小时。用乙酸乙酯萃取该混合物，并且合并有机相。将溶剂蒸干。向固体中添加约150mL20％乙酸乙酯/己烷。将该混合物搅拌数小时，然后过滤。将过滤出的固体用己烷洗涤3次。得到约4.5g白色固体产物，该产物由1HNMR证实。
5.化合物25S的合成
将3.5g(7.67mmol)2,4,8-三苯基二苯并噻吩-6-硼酸，3.2g(6.98mmol)三氟甲磺酸3-(苯并[9,10]菲-2-基)苯基酯，64mg(0.077mmol)Pd2(dba)3，115mg(0.30mmol)S-phose，4.5g(22mmol)K3PO4，90mL甲苯和10mL水加入到一个250mL烧瓶中。将该混合物在氮气氛下加热回流过夜。反应混合物用分液漏斗分离，并且有机相通过使用25％二氯甲烷/己烷作为洗脱剂的硅胶柱层析和从甲苯和己烷混合物中重结晶来纯化。得到约4.5g(92％)白色固体产物，该产物通过1HNMR证实。
实施例14化合物2O
将3.9g(18.4mmol)二苯并呋喃-4-硼酸，7.0g(15.4mmol)三氟甲磺酸3-(苯并[9,10]菲-2-基)苯基酯，141mg(0.154mmol)Pd2(dba)3，252mg(0.46mmol)S-phose，9.8g(46mmol)K3PO4，180mL甲苯和20mL水加入到一个500mL烧瓶中。将该混合物在氮气氛下加热回流过夜。反应混合物用分液漏斗分离，并且有机相通过硅胶柱层析纯化，使用20％二氯甲烷/己烷作为洗脱剂。得到约6.2g(87％)白色固体产物，该产物通过1HNMR证实。
器件实施例
所有实施例器件通过高真空(<10－7托)热蒸发来制备。阳极电极是约800或1200埃的氧化铟锡(ITO)。阴极由10埃的LiF和后面的1,000埃的Al组成。所有器件在制造之后马上在氮气手套箱(<1ppm的H2O和O2)中用玻璃盖子盖上并用环氧树脂密封，并且在包装内引入吸湿气剂。
表1和2中的器件实施例1-30的有机堆叠物由如下物质组成：从ITO表面开始依次地，作为空穴注入层(HIL)的的化合物A，作为空穴传输层(HTL)的的4,4’-双[N-(1-萘基)-N-苯基氨基]联苯(α-NPD)，作为发射层(EML)的的用10或15wt％Ir磷光性化合物掺杂的本发明化合物，作为ETL2的50或的HPT或本发明化合物，和作为ETL1的400或的Alq3(三(8-羟基喹啉)铝)。
对比例1和2类似于所述器件实施例制造，但是使用CBP作为主体。
器件结构和数据总结在表1－5中。表1显示了器件结构，表2显示了这些器件的相应的测量结果，而表3－5各自显示了器件结构和测量的实验结果。在这里使用的化合物A、化合物B、NPD和HPT具有如下结构:
表1
表2
从器件实施例1-30可以看到，化合物1S、2S、20S、9S、23S、24S和2O作为绿色磷光OLED中的主体给出了高的器件效率(在1000cd/m2下LE>40cd/A)，表明苯并[9,10]菲和苯并噻吩的组合(无论直接连接或由间亚苯基连接)具有对于有效的绿色场致磷光来说足够高的三重态能量。
可以注意到结合有作为主体的化合物1S、2S、21S、23S和2O的器件的高稳定性。器件实施例1和对比例2仅主体不同。器件实施例1使用化合物1作为主体，而对比例2使用通常使用的主体CBP。寿命T80％(定义为在室温下在40mA/cm2的恒定电流密度下初始发光度L0衰减到其值的80％时所要求的时间)分别为270小时和105小时，而器件实施例1具有略高的L0。这相当于几乎3倍的器件稳定性改进。类似地，使用化合物2S作为主体的器件实施例5比对比例2稳定至少1.5倍。使用化合物2S作为主体的器件实施例9比使用CBP作为主体的对比例1稳定至少2倍。还可以注意到，所述化合物可以很好地用作增进层材料(ETL2)。器件实施例10和器件实施例9都含有化合物2S作为主体，但是分别含有化合物2和HPT作为增进层。器件实施例10和器件实施例9分别具有450和380小时的T0.8，表明了化合物2S作为增进层材料的好的性能。器件实施例21具有620小时的T0.8，该数值显著高于使用CBP的对比例1或2器件的寿命。
所述数据表明，含苯并[9,10]菲的苯并噻吩类，特别是含苯并[9,10]菲的二苯并噻吩类，是优异的磷光OLED的主体和增进层材料，与通常使用的作为主体的CBP相比，它们提供了至少相当的效率和多倍的稳定性改进。含苯并[9,10]菲的苯并噻吩类的更共轭的变体，例如通过对亚苯基(例如4,4'-联苯基)连接的苯并[9,10]菲和苯并噻吩单元，可能非常适合较低能量(黄－红)的磷光OLED。
表3显示了某些器件的器件结构和测量的实验结果，所述器件具有在第一有机层和第二有机层间具有界面的发射层，其中在两个层中主体和掺杂剂(即非发射材料)是相同的材料，并且在两个层中磷光材料是相同的材料，但是浓度不同。表3中的所有器件具有的化合物A组成的空穴注入层，的不同材料(取决于具体的器件)组成的增进层(ETL2)，的电子传输层(ETL1),和LiF/Al阴极。所述发射层包括第一有机层和第二有机层，在所述两层间有界面，其中第一有机层是浓度为70wt％的非发射材料(表3中的“主体”)和浓度为30wt％的磷光材料(表3中的“掺杂剂”)组成的的层,并且第二有机层是相同但浓度为90wt％的非发射材料(表3中的“主体”)和相同但浓度为10wt％的磷光材料(表3中的“掺杂剂”)组成的的层。每个器件的具体的主体和掺杂剂在表3中指明。因此，表3的器件的通用器件结构为:ITO/化合物/主体(70wt％):掺杂剂(30wt％)/主体(90wt％):掺杂剂(10wt％)/ETL2/Alq3 /LiF/Al。
表3
使用化合物2S作为主体和化合物2S或HPT作为增进层材料的表3中器件显示了高的效率(在1000cd/m2下>46cd/A)。甚至更值得注意的是1000小时(器件实施例A、B和D)或甚至2000小时(器件实施例C)的LT80％的稳定性，这样的稳定性使得这些器件属于迄今为止最长寿命的绿色磷光OLED。
含有苯并[9,10]菲-苯并噻吩杂化体的器件的好的性能和高的稳定性据信是苯并[9,10]菲和苯并噻吩电荷传输单元所提供的好的电荷平衡以及由于苯并噻吩和苯并[9,10]菲单元所提供的π-共轭导致的分子氧化/还原态的稳定化的结果。
表4和表5显示了一些器件的器件结构和测量的实验结果，所述器件具有含有连接到中心吡啶的苯并[9,10]菲和苯并稠合的噻吩的发射层。
表4中所有的器件具有的由化合物A组成的空穴注入层，的由NPD组成的空穴传输层，的含有化合物21S作为主体和化合物A作为掺杂剂的发射层，具有表4中指明的材料和厚度的封闭层(BL)，具有表4中指明的厚度的、由Alq组成的电子传输层(ETL),和LiF/Al阴极。特别地，BL厚度和ETL厚度的总和为所述发射层是包括主体和掺杂剂的单一层。每个器件中掺杂剂的具体百分比在表4中指明。因此，表4的通用器件结构为:ITO/化合物A/NPD/化合物21S:化合物Ax％)/BL/Alq(-BL)/LiF(10)/Al(1000)。
表4
表5中所有的器件具有的由化合物A组成的空穴注入层，的具有表5中指明的材料的空穴传输层，的含有化合物22S作为主体和化合物A作为掺杂剂的发射层，具有表5中指明的材料和厚度的封闭层(BL)，具有减去封闭层(BL)厚度的厚度的电子传输层,和LiF/Al阴极。特别地，所述BL厚度和ETL厚度的总和为所述发射层是包括主体和掺杂剂的单一层。每个器件中具体百分比在表5中指明。因此，表5的通用器件结构为:ITO/化合物A100/HTL/化合物22S:化合物Ax％/BL/Alq(-BL)/LiF(10)/Al(1000)。
表5
*外推的数据
应该理解，本文中描述的各种实施方案仅是为了举例说明，并且不是意图限制本发明的范围。例如，在不脱离本发明的精神的情况下，在这里描述的许多材料和结构可以被其它材料和结构取代。因此，要求保护的本发明可以包括本文中描述的特定实施例和优选实施方案的变例，这一点对于本领域技术人员来说是显而易见的。特别地，所述含苯并[9,10]菲的基团可以连接到苯并噻吩或苯并呋喃的任何位置。应该理解，关于本发明为什么发挥作用的各种理论并不是意图是限制性的。
Claims (20)
1.由式(IV)或式(V)的结构表示的化合物:
其中X是S或O；
其中R2表示单、二、三、四或非取代；
其中R1’表示单、二或非取代；
其中R1、R1’、R2和R3各自是非稠合的取代基，所述取代基独立地选自H，CnH2n+1，OCnH2n+1，OAr1，N(CnH2n+1)2，N(Ar1)(Ar2)，CH＝CH-CnH2n+1，C≡CCnH2n+1，Ar1，Ar1-Ar2，CnH2n-Ar1，其中n是1，2，3，4，5，6，7，8，9或者10，
其中Ar1和Ar2独立地选自苯、联苯、萘、苯并[9,10]菲、咔唑和它们的杂芳族类似物；和
其中R1、R1’、R2和R3中至少一个包括苯并[9,10]菲基团。
2.权利要求1的化合物，其中所述化合物由式(IV)的结构表示:
3.权利要求2的化合物，其中X是S。
4.权利要求2的化合物，其中X是O。
5.权利要求2的化合物，其中所述化合物由如下结构表示:
其中R4、R5、R8和R9独立地表示单、二、三、四或非取代；
其中R6和R8独立地表示单、二、三或非取代；和
其中R4、R5、R6、R7、R8和R9各自独立地选自H，CnH2n+1，OCnH2n+1，OAr1，N(CnH2n+1)2，N(Ar1)(Ar2)，CH＝CH-CnH2n+1，C≡CCnH2n+1，Ar1，Ar1-Ar2，CnH2n-Ar1。
6.权利要求5的化合物，其中X是S。
7.权利要求5的化合物，其中X是O。
8.权利要求1的化合物，其中所述化合物由式(V)的结构表示:
9.权利要求8的化合物，其中X是S。
10.权利要求8的化合物，其中X是O。
11.权利要求8的化合物，其中所述化合物选自下组:
其中R1”和R2’各自是非稠合的取代基，所述取代基独立地选自H，CnH2n+1，OCnH2n+1，OAr1，N(CnH2n+1)2，N(Ar1)(Ar2)，CH＝CH-CnH2n+1，C≡CCnH2n+1，Ar1，Ar1-Ar2，CnH2n-Ar1；
其中R4和R5独立地表示单、二、三、四或非取代；
其中R6和R2’独立地表示单、二、三或非取代；和
其中R4、R5和R6各自独立地选自H，CnH2n+1，OCnH2n+1，OAr1，N(CnH2n+1)2，N(Ar1)(Ar2)，CH＝CH-CnH2n+1，C≡CCnH2n+1，Ar1，Ar1-Ar2，CnH2n-Ar1。
12.权利要求11的化合物，其中X是S。
13.权利要求11的化合物，其中X是O。
14.权利要求1的化合物，其中Ar1和Ar2独立地选自苯、联苯、萘、苯并[9,10]菲和咔唑。
15.有机发光器件，其包含:
阳极；
阴极；
布置在所述阳极和所述阴极之间的有机层，其中所述有机层包含由式(IV)或式(V)的结构表示的化合物:
其中X是S或O；
其中R2表示单、二、三、四或非取代；
其中R1’表示单、二或非取代；
其中R1、R1’、R2和R3各自是非稠合的取代基，所述取代基独立地选自H，CnH2n+1，OCnH2n+1，OAr1，N(CnH2n+1)2，N(Ar1)(Ar2)，CH＝CH-CnH2n+1，C≡CCnH2n+1，Ar1，Ar1-Ar2，CnH2n-Ar1，其中n是1，2，3，4，5，6，7，8，9或者10，
其中Ar1和Ar2独立地选自苯、联苯、萘、苯并[9,10]菲、咔唑和它们的杂芳族类似物；和
其中R1、R1’、R2和R3中至少一个包括苯并[9,10]菲基团。
16.权利要求15的器件，其中所述有机层是发射层。
17.权利要求16的器件，其中所述有机层还包含磷光性发射体。
18.权利要求17的器件，其中所述磷光性发射体是铱络合物。
19.权利要求15的器件，其中所述有机层包含化合物2S和铱络合物。
20.权利要求15的器件，其中Ar1和Ar2独立地选自苯、联苯、萘、苯并[9,10]菲和咔唑。
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US96394407P | 2007-08-08 | 2007-08-08 | |
| US60/963,944 | 2007-08-08 | ||
| US1750607P | 2007-12-28 | 2007-12-28 | |
| US1739107P | 2007-12-28 | 2007-12-28 | |
| US61/017,391 | 2007-12-28 | ||
| US61/017,506 | 2007-12-28 | ||
| CN200880106949.2A CN101827834B (zh) | 2007-08-08 | 2008-08-07 | 含苯并[9，10]菲的苯并稠合的噻吩或苯并稠合的呋喃化合物 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200880106949.2A Division CN101827834B (zh) | 2007-08-08 | 2008-08-07 | 含苯并[9，10]菲的苯并稠合的噻吩或苯并稠合的呋喃化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105367544A true CN105367544A (zh) | 2016-03-02 |
| CN105367544B CN105367544B (zh) | 2018-03-02 |
Family
ID=42102946
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410503620.7A Active CN104311533B (zh) | 2007-08-08 | 2008-08-07 | 含苯并[9,10]菲的苯并稠合的噻吩或苯并稠合的呋喃化合物 |
| CN200880106949.2A Active CN101827834B (zh) | 2007-08-08 | 2008-08-07 | 含苯并[9，10]菲的苯并稠合的噻吩或苯并稠合的呋喃化合物 |
| CN201510646336.XA Active CN105367544B (zh) | 2007-08-08 | 2008-08-07 | 含苯并[9,10]菲的苯并稠合的噻吩或苯并稠合的呋喃化合物 |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410503620.7A Active CN104311533B (zh) | 2007-08-08 | 2008-08-07 | 含苯并[9,10]菲的苯并稠合的噻吩或苯并稠合的呋喃化合物 |
| CN200880106949.2A Active CN101827834B (zh) | 2007-08-08 | 2008-08-07 | 含苯并[9，10]菲的苯并稠合的噻吩或苯并稠合的呋喃化合物 |
Country Status (7)
| Country | Link |
|---|---|
| US (6) | US8367850B2 (zh) |
| EP (2) | EP3159333B1 (zh) |
| JP (5) | JP6009144B2 (zh) |
| KR (4) | KR20160086983A (zh) |
| CN (3) | CN104311533B (zh) |
| TW (3) | TWI531567B (zh) |
| WO (1) | WO2009021126A2 (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112409416A (zh) * | 2019-08-21 | 2021-02-26 | 环球展览公司 | 有机电致发光材料和装置 |
Families Citing this family (624)
| 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 |
| US8586204B2 (en) | 2007-12-28 | 2013-11-19 | Universal Display Corporation | Phosphorescent emitters and host materials with improved stability |
| KR20160030582A (ko) | 2006-02-10 | 2016-03-18 | 유니버셜 디스플레이 코포레이션 | 시클로금속화 이미다조[1,2-ｆ]페난트리딘 및 디이미다조[1,2-ａ:1'',2''-ｃ]퀴나졸린 리간드, 및 이의 등전자성 및 벤즈고리화된 유사체의 금속 착체 |
| 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 |
| US8431243B2 (en) | 2007-03-08 | 2013-04-30 | Universal Display Corporation | Phosphorescent materials containing iridium complexes |
| KR20160104752A (ko) | 2007-08-08 | 2016-09-05 | 유니버셜 디스플레이 코포레이션 | 인광성 발광 다이오드의 단일 트리페닐렌 발색단 |
| KR20160086983A (ko) | 2007-08-08 | 2016-07-20 | 유니버셜 디스플레이 코포레이션 | 트리페닐렌기를 포함하는 벤조 융합 티오펜 또는 벤조 융합 푸란 화합물 |
| WO2009073245A1 (en) | 2007-12-06 | 2009-06-11 | Universal Display Corporation | Light-emitting organometallic complexes |
| WO2009085344A2 (en) | 2007-12-28 | 2009-07-09 | Universal Display Corporation | Dibenzothiophene-containing materials in phosphorescent light emitting diodes |
| 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 |
| CN102160206B (zh) | 2008-09-25 | 2014-06-11 | 通用显示公司 | 有机硒物质及其在有机发光装置中的用途 |
| WO2010056669A1 (en) * | 2008-11-11 | 2010-05-20 | Universal Display Corporation | Phosphorescent emitters |
| 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 |
| WO2010095564A1 (ja) * | 2009-02-18 | 2010-08-26 | 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 |
| US8722205B2 (en) * | 2009-03-23 | 2014-05-13 | Universal Display Corporation | Heteroleptic iridium complex |
| US11910700B2 (en) | 2009-03-23 | 2024-02-20 | Universal Display Corporation | Heteroleptic iridium complexes as dopants |
| US8709615B2 (en) * | 2011-07-28 | 2014-04-29 | Universal Display Corporation | Heteroleptic iridium complexes as dopants |
| TWI609855B (zh) * | 2009-04-28 | 2018-01-01 | 環球展覽公司 | 具有甲基-ｄ３取代之銥錯合物 |
| TWI541234B (zh) * | 2009-05-12 | 2016-07-11 | 環球展覽公司 | 用於有機發光二極體之２－氮雜聯伸三苯材料 |
| US8586203B2 (en) | 2009-05-20 | 2013-11-19 | Universal Display Corporation | Metal complexes with boron-nitrogen heterocycle containing ligands |
| KR101707430B1 (ko) | 2009-05-29 | 2017-02-16 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 발광 소자, 발광 장치, 조명 장치 및 전자기기 |
| US9741955B2 (en) * | 2009-05-29 | 2017-08-22 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element, light-emitting device, and method for manufacturing the same |
| KR101724304B1 (ko) * | 2009-10-16 | 2017-04-10 | 에스에프씨 주식회사 | 축합방향족 화합물 및 이를 포함하는 유기전계발광소자 |
| WO2011052516A1 (en) | 2009-11-02 | 2011-05-05 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex, light-emitting element, display device, electronic device, and lighting device |
| US8580394B2 (en) | 2009-11-19 | 2013-11-12 | Universal Display Corporation | 3-coordinate copper(I)-carbene complexes |
| KR101170220B1 (ko) * | 2009-12-30 | 2012-07-31 | 주식회사 두산 | 트리페닐렌계 화합물 및 이를 포함하는 유기 전계 발광 소자 |
| JP4691611B1 (ja) | 2010-01-15 | 2011-06-01 | 富士フイルム株式会社 | 有機電界発光素子 |
| CN102473857A (zh) | 2010-01-15 | 2012-05-23 | 出光兴产株式会社 | 有机电致发光元件 |
| US8288187B2 (en) | 2010-01-20 | 2012-10-16 | Universal Display Corporation | Electroluminescent devices for lighting applications |
| 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 |
| EP2550690B1 (en) | 2010-03-25 | 2018-12-26 | Universal Display Corporation | Solution processable doped triarylamine hole injection materials |
| CN103026521B (zh) * | 2010-04-28 | 2016-11-09 | 通用显示公司 | 沉积预混合的材料 |
| US8968887B2 (en) * | 2010-04-28 | 2015-03-03 | Universal Display Corporation | Triphenylene-benzofuran/benzothiophene/benzoselenophene compounds with substituents joining to form fused rings |
| US8993125B2 (en) | 2010-05-21 | 2015-03-31 | Semiconductor Energy Laboratory Co., Ltd. | Triazole derivative, and light-emitting element, light-emitting device, electronic device and lighting device using the triazole derivative |
| KR101244599B1 (ko) | 2010-05-28 | 2013-03-25 | 주식회사 두산 | 바이폴라 트리페닐렌계 화합물 및 이를 포함하는 유기 전계 발광 소자 |
| US8742657B2 (en) | 2010-06-11 | 2014-06-03 | Universal Display Corporation | Triplet-Triplet annihilation up conversion (TTA-UC) for display and lighting applications |
| US8673458B2 (en) | 2010-06-11 | 2014-03-18 | Universal Display Corporation | Delayed fluorescence OLED |
| JP4751954B1 (ja) | 2010-07-09 | 2011-08-17 | 富士フイルム株式会社 | 有機電界発光素子 |
| WO2012016074A1 (en) | 2010-07-29 | 2012-02-02 | University Of Southern California | Co-deposition methods for the fabrication of organic optoelectronic devices |
| JP5507381B2 (ja) | 2010-07-30 | 2014-05-28 | 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 |
| US9954180B2 (en) | 2010-08-20 | 2018-04-24 | Universal Display Corporation | Bicarbazole compounds for OLEDs |
| 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 |
| JP5735241B2 (ja) * | 2010-09-08 | 2015-06-17 | 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電荷輸送材料 |
| 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 |
| WO2012033108A1 (en) | 2010-09-10 | 2012-03-15 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element and electronic device |
| WO2012039561A1 (en) * | 2010-09-20 | 2012-03-29 | Rohm And Haas Electronic Materials Korea Ltd. | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| JP5623996B2 (ja) | 2010-09-21 | 2014-11-12 | 株式会社半導体エネルギー研究所 | カルバゾール誘導体 |
| JP5856266B2 (ja) * | 2010-09-21 | 2016-02-09 | 株式会社半導体エネルギー研究所 | 有機半導体素子 |
| JP5729957B2 (ja) * | 2010-09-29 | 2015-06-03 | キヤノン株式会社 | ジベンゾチオフェン化合物およびそれを有する有機発光素子 |
| KR101912675B1 (ko) * | 2010-10-04 | 2018-10-29 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 복합 재료, 발광 소자, 발광 장치, 전자 기기, 및 조명 장치 |
| US8932734B2 (en) | 2010-10-08 | 2015-01-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| DE102010048608A1 (de) * | 2010-10-15 | 2012-04-19 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
| KR101950363B1 (ko) * | 2010-10-29 | 2019-02-20 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 페난트렌 화합물, 발광 소자, 발광 장치, 전자 기기, 및 조명 장치 |
| JP5669539B2 (ja) | 2010-12-01 | 2015-02-12 | キヤノン株式会社 | キノリノ［３，２，１−ｋｌ］フェノキサジン化合物及びこれを用いた有機発光素子 |
| KR101531612B1 (ko) | 2010-12-02 | 2015-06-25 | 제일모직 주식회사 | 유기광전소자용 화합물 및 이를 포함하는 유기광전소자 |
| US20120138906A1 (en) | 2010-12-07 | 2012-06-07 | The University of Southern California USC Stevens Institute for Innovation | Capture agents for unsaturated metal complexes |
| US10008677B2 (en) | 2011-01-13 | 2018-06-26 | Universal Display Corporation | Materials for organic light emitting diode |
| JP2012153628A (ja) * | 2011-01-25 | 2012-08-16 | Canon Inc | ジベンゾチオフェンジオキサイド化合物及びこれを用いた有機発光素子 |
| US9067916B2 (en) * | 2011-02-01 | 2015-06-30 | Semiconductor Energy Laboratory Co., Ltd. | Heterocyclic compound |
| US9056856B2 (en) | 2011-02-01 | 2015-06-16 | Semiconductor Energy Laboratory Co., Ltd. | Heterocyclic compound |
| US9005772B2 (en) | 2011-02-23 | 2015-04-14 | Universal Display Corporation | Thioazole and oxazole carbene metal complexes as phosphorescent OLED materials |
| CN111732611B (zh) | 2011-02-23 | 2022-08-23 | 通用显示公司 | 新型的四齿铂络合物 |
| US8563737B2 (en) | 2011-02-23 | 2013-10-22 | Universal Display Corporation | Methods of making bis-tridentate carbene complexes of ruthenium and osmium |
| US8883322B2 (en) | 2011-03-08 | 2014-11-11 | Universal Display Corporation | Pyridyl carbene phosphorescent emitters |
| EP2503618B1 (en) | 2011-03-23 | 2014-01-01 | Semiconductor Energy Laboratory Co., Ltd. | Composite material, light-emitting element, light-emitting device, electronic device, and lighting device |
| JP5973762B2 (ja) * | 2011-03-31 | 2016-08-23 | ユー・ディー・シー アイルランド リミテッド | 電荷輸送材料、有機電界発光素子及び該素子を用いたことを特徴とする発光装置、表示装置または照明装置 |
| JP5984450B2 (ja) | 2011-03-31 | 2016-09-06 | 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、並びに、該素子を用いた発光装置、表示装置、照明装置及び該素子用の化合物 |
| US8927308B2 (en) | 2011-05-12 | 2015-01-06 | Universal Display Corporation | Method of forming bus line designs for large-area OLED lighting |
| US8432095B2 (en) | 2011-05-11 | 2013-04-30 | Universal Display Corporation | Process for fabricating metal bus lines for OLED lighting panels |
| US8795850B2 (en) | 2011-05-19 | 2014-08-05 | Universal Display Corporation | Phosphorescent heteroleptic phenylbenzimidazole dopants and new synthetic methodology |
| US9212197B2 (en) | 2011-05-19 | 2015-12-15 | Universal Display Corporation | Phosphorescent heteroleptic phenylbenzimidazole dopants |
| 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 |
| WO2012170461A1 (en) | 2011-06-08 | 2012-12-13 | Universal Display Corporation | Heteroleptic iridium carbene complexes and light emitting device using them |
| 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 |
| JP5804797B2 (ja) | 2011-06-28 | 2015-11-04 | キヤノン株式会社 | ベンゾトリフェニレノフラン化合物およびそれを有する有機発光素子 |
| US9309223B2 (en) * | 2011-07-08 | 2016-04-12 | Semiconductor Energy Laboratory Co., Ltd. | Heterocyclic compound, light-emitting element, light-emitting device, electronic device, and lighting device |
| US9397310B2 (en) | 2011-07-14 | 2016-07-19 | Universal Display Corporation | Organice electroluminescent materials and devices |
| US9023420B2 (en) | 2011-07-14 | 2015-05-05 | Universal Display Corporation | Composite organic/inorganic layer for organic light-emitting 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 |
| TWI561527B (en) * | 2011-07-25 | 2016-12-11 | Universal Display Corp | Tetradentate platinum complexes |
| US8926119B2 (en) | 2011-08-04 | 2015-01-06 | Universal Display Corporation | Extendable light source with variable light emitting area |
| WO2013022419A1 (en) | 2011-08-05 | 2013-02-14 | Universal Display Corporation | Phosphorescent organic light emitting devices combined with hole transport material having high operating stability |
| US9029558B2 (en) | 2011-08-18 | 2015-05-12 | Semiconductor Energy Laboratory Co., Ltd. | Carbazole compound, light-emitting element, light-emitting device, electronic device, and lighting device |
| CN103765624B (zh) * | 2011-08-31 | 2016-08-17 | 株式会社半导体能源研究所 | 发光元件、发光装置、电子设备、照明装置及杂环化合物 |
| US9493698B2 (en) | 2011-08-31 | 2016-11-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| 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 |
| 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 |
| US8987451B2 (en) | 2012-01-03 | 2015-03-24 | Universal Display Corporation | Synthesis of cyclometallated platinum(II) complexes |
| US9461254B2 (en) | 2012-01-03 | 2016-10-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| 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 |
| US9386657B2 (en) | 2012-03-15 | 2016-07-05 | Universal Display Corporation | Organic Electroluminescent materials and devices |
| US9054323B2 (en) | 2012-03-15 | 2015-06-09 | Universal Display Corporation | Secondary hole transporting layer with diarylamino-phenyl-carbazole compounds |
| 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 |
| US20140014930A1 (en) * | 2012-07-13 | 2014-01-16 | Semiconductor Energy Laboratory Co., Ltd. | Organic Compound, Light-Emitting Element, Light-Emitting Device, Electronic Device, and Lighting Device |
| 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 |
| US9540329B2 (en) * | 2012-07-19 | 2017-01-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| 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 |
| US9978958B2 (en) * | 2012-08-24 | 2018-05-22 | Universal Display Corporation | Phosphorescent emitters with phenylimidazole ligands |
| JP6217642B2 (ja) | 2012-08-24 | 2017-10-25 | 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 |
| 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 |
| 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 |
| 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 |
| US8946697B1 (en) | 2012-11-09 | 2015-02-03 | Universal Display Corporation | Iridium complexes with aza-benzo fused ligands |
| US9634264B2 (en) | 2012-11-09 | 2017-04-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9748500B2 (en) | 2015-01-15 | 2017-08-29 | Universal Display Corporation | Organic light emitting materials |
| US9685617B2 (en) | 2012-11-09 | 2017-06-20 | Universal Display Corporation | Organic electronuminescent materials and devices |
| US10069090B2 (en) | 2012-11-20 | 2018-09-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9190623B2 (en) | 2012-11-20 | 2015-11-17 | 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 |
| US9653691B2 (en) | 2012-12-12 | 2017-05-16 | Universal Display Corporation | Phosphorescence-sensitizing fluorescence material system |
| CN104885247B (zh) * | 2012-12-17 | 2017-05-10 | 新日铁住金化学株式会社 | 有机电场发光元件 |
| KR102052739B1 (ko) | 2012-12-26 | 2019-12-06 | 엘지디스플레이 주식회사 | 인광 화합물 및 이를 사용한 유기전계발광소자 |
| JP5911418B2 (ja) | 2012-12-27 | 2016-04-27 | キヤノン株式会社 | 有機発光素子 |
| JP6095391B2 (ja) * | 2013-02-06 | 2017-03-15 | キヤノン株式会社 | 有機発光素子 |
| 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 |
| JP2014187130A (ja) * | 2013-03-22 | 2014-10-02 | Nippon Hoso Kyokai <Nhk> | 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、正孔輸送材料の評価方法 |
| KR102257137B1 (ko) | 2013-03-26 | 2021-05-26 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 발광 소자, 화합물, 유기 화합물, 디스플레이 모듈, 조명 모듈, 발광 장치, 표시 장치, 조명 장치 및 전자 기기 |
| 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 |
| 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 |
| KR101433822B1 (ko) | 2013-06-17 | 2014-08-27 | 삼성디스플레이 주식회사 | 유기 발광 장치 |
| KR102188028B1 (ko) | 2013-06-18 | 2020-12-08 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
| WO2014204464A1 (en) * | 2013-06-20 | 2014-12-24 | Universal Display Corporation | Phosphorescent organic light emitting devices having a hole-transporting host in the emissive region |
| 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 |
| 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 |
| US9553274B2 (en) | 2013-07-16 | 2017-01-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9324949B2 (en) | 2013-07-16 | 2016-04-26 | 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 |
| KR101686078B1 (ko) * | 2013-08-12 | 2016-12-13 | 제일모직 주식회사 | 조성물, 유기 광전자 소자 및 표시 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 |
| 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 |
| KR101648142B1 (ko) * | 2013-10-21 | 2016-08-12 | 제일모직 주식회사 | 조성물, 유기 광전자 소자 및 표시 장치 |
| US9853229B2 (en) | 2013-10-23 | 2017-12-26 | University Of Southern California | Organic electroluminescent materials and devices |
| JP6522313B2 (ja) * | 2013-10-24 | 2019-05-29 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子および電子機器 |
| 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 |
| KR102177211B1 (ko) * | 2013-12-05 | 2020-11-11 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
| 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 |
| 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 |
| CN104795503B (zh) | 2014-01-16 | 2018-07-20 | 三星显示有限公司 | 有机发光装置 |
| 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 |
| KR102280686B1 (ko) | 2014-02-11 | 2021-07-22 | 삼성전자주식회사 | 카바졸계 화합물 및 이를 포함한 유기 발광 소자 |
| 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 |
| US9502656B2 (en) | 2014-02-24 | 2016-11-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9647217B2 (en) | 2014-02-24 | 2017-05-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| KR102269920B1 (ko) | 2014-02-25 | 2021-06-28 | 삼성디스플레이 주식회사 | 유기 화합물 및 이를 포함하는 유기 발광 장치 |
| US10403825B2 (en) | 2014-02-27 | 2019-09-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9590195B2 (en) | 2014-02-28 | 2017-03-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9673407B2 (en) * | 2014-02-28 | 2017-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9181270B2 (en) | 2014-02-28 | 2015-11-10 | Universal Display Corporation | Method of making sulfide compounds |
| US9190620B2 (en) | 2014-03-01 | 2015-11-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| WO2015134017A1 (en) | 2014-03-05 | 2015-09-11 | Universal Display Corporation | Phosphorescent oled devices |
| US9397309B2 (en) | 2014-03-13 | 2016-07-19 | Universal Display Corporation | Organic electroluminescent devices |
| US20170092875A1 (en) * | 2014-03-18 | 2017-03-30 | Merck Patent Gmbh | Organic electroluminescent device |
| 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 |
| 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 |
| US10008679B2 (en) | 2014-04-14 | 2018-06-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9847498B2 (en) | 2014-04-14 | 2017-12-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9450198B2 (en) | 2014-04-15 | 2016-09-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10256427B2 (en) | 2014-04-15 | 2019-04-09 | Universal Display Corporation | Efficient organic electroluminescent devices |
| US9741941B2 (en) | 2014-04-29 | 2017-08-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| KR102255197B1 (ko) | 2014-05-02 | 2021-05-25 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
| US10457699B2 (en) | 2014-05-02 | 2019-10-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| KR102124045B1 (ko) * | 2014-05-02 | 2020-06-18 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
| CN106463619B (zh) | 2014-05-08 | 2020-07-07 | 环球展览公司 | 稳定的咪唑并菲啶材料 |
| US10403830B2 (en) | 2014-05-08 | 2019-09-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| 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 |
| KR102253442B1 (ko) * | 2014-05-13 | 2021-05-20 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
| 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 |
| DE102014008722B4 (de) | 2014-06-18 | 2024-08-22 | Merck Patent Gmbh | Zusammensetzungen für elektronische Vorrichtungen, Formulierung diese enthaltend, Verwendung der Zusammensetzung, Verwendung der Formulierung sowie organische elektronische Vorrichtung enthaltend die Zusammensetzung |
| 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 |
| 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 |
| TWI690534B (zh) | 2014-08-08 | 2020-04-11 | 愛爾蘭商Ｕｄｃ愛爾蘭責任有限公司 | 電致發光咪唑并喹噁啉碳烯金屬錯合物 |
| US9944846B2 (en) | 2014-08-28 | 2018-04-17 | E I Du Pont De Nemours And Company | Compositions for electronic applications |
| US10741772B2 (en) | 2014-08-29 | 2020-08-11 | Samsung Electronics Co., Ltd. | Organic light-emitting device |
| KR102256932B1 (ko) | 2014-09-18 | 2021-05-28 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
| 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 |
| US10749113B2 (en) | 2014-09-29 | 2020-08-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10361375B2 (en) | 2014-10-06 | 2019-07-23 | 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 |
| US9397302B2 (en) | 2014-10-08 | 2016-07-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10950803B2 (en) | 2014-10-13 | 2021-03-16 | Universal Display Corporation | Compounds and uses in devices |
| CN105503518A (zh) * | 2014-10-14 | 2016-04-20 | 上海华显新材料科技有限公司 | 高纯度2-溴三亚苯的制备方法 |
| KR102417121B1 (ko) * | 2014-10-17 | 2022-07-06 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
| US9484541B2 (en) | 2014-10-20 | 2016-11-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
| KR102285389B1 (ko) * | 2014-11-05 | 2021-08-04 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
| US10868261B2 (en) * | 2014-11-10 | 2020-12-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10038151B2 (en) | 2014-11-12 | 2018-07-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10411201B2 (en) | 2014-11-12 | 2019-09-10 | 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 |
| US9761814B2 (en) | 2014-11-18 | 2017-09-12 | Universal Display Corporation | Organic light-emitting materials and devices |
| WO2016079169A1 (en) | 2014-11-18 | 2016-05-26 | Basf Se | Pt- or pd-carbene complexes for use in organic light emitting diodes |
| KR102366567B1 (ko) | 2014-11-19 | 2022-02-25 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
| US9444075B2 (en) | 2014-11-26 | 2016-09-13 | Universal Display Corporation | Emissive display with photo-switchable polarization |
| US9450195B2 (en) | 2014-12-17 | 2016-09-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| 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 |
| US9711730B2 (en) | 2015-01-25 | 2017-07-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10418569B2 (en) | 2015-01-25 | 2019-09-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10644247B2 (en) | 2015-02-06 | 2020-05-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10418562B2 (en) | 2015-02-06 | 2019-09-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10355222B2 (en) | 2015-02-06 | 2019-07-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
| 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 |
| 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 |
| 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 |
| US10297770B2 (en) | 2015-03-27 | 2019-05-21 | 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 |
| US10693082B2 (en) | 2015-04-06 | 2020-06-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| JP6109231B2 (ja) * | 2015-04-16 | 2017-04-05 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子及び電荷輸送材料 |
| US10403826B2 (en) | 2015-05-07 | 2019-09-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10777749B2 (en) | 2015-05-07 | 2020-09-15 | 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 |
| US10109799B2 (en) | 2015-05-21 | 2018-10-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10256411B2 (en) | 2015-05-21 | 2019-04-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| KR20180013958A (ko) | 2015-05-29 | 2018-02-07 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 발광 소자, 발광 장치, 표시 장치, 전자 기기, 및 조명 장치 |
| US10418568B2 (en) | 2015-06-01 | 2019-09-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10033004B2 (en) | 2015-06-01 | 2018-07-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11925102B2 (en) | 2015-06-04 | 2024-03-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10818853B2 (en) | 2015-06-04 | 2020-10-27 | University Of Southern California | 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 |
| KR102490887B1 (ko) | 2015-09-11 | 2023-01-25 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
| 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 |
| US10847728B2 (en) | 2015-10-01 | 2020-11-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10593892B2 (en) | 2015-10-01 | 2020-03-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| 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 |
| KR102524531B1 (ko) | 2015-11-03 | 2023-04-24 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
| US10998507B2 (en) * | 2015-11-23 | 2021-05-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10476010B2 (en) | 2015-11-30 | 2019-11-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| KR20170069342A (ko) * | 2015-12-10 | 2017-06-21 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
| KR102684614B1 (ko) | 2015-12-21 | 2024-07-15 | 유디씨 아일랜드 리미티드 | 삼각형 리간드를 갖는 전이 금속 착체 및 ｏｌｅｄ에서의 이의 용도 |
| KR20180095919A (ko) | 2015-12-25 | 2018-08-28 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 화합물, 발광 소자, 표시 장치, 전자 기기, 및 조명 장치 |
| 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 |
| US10707427B2 (en) | 2016-02-09 | 2020-07-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
| 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 |
| US10600967B2 (en) | 2016-02-18 | 2020-03-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| 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 |
| US10566552B2 (en) | 2016-04-13 | 2020-02-18 | 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 |
| US11228003B2 (en) | 2016-04-22 | 2022-01-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20170324049A1 (en) | 2016-05-05 | 2017-11-09 | Universal Display Corporation | Organic Electroluminescent Materials and Devices |
| 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 |
| US10686140B2 (en) | 2016-06-20 | 2020-06-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10727423B2 (en) | 2016-06-20 | 2020-07-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11482683B2 (en) | 2016-06-20 | 2022-10-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10651403B2 (en) | 2016-06-20 | 2020-05-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10672997B2 (en) | 2016-06-20 | 2020-06-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| JP7039188B2 (ja) * | 2016-06-24 | 2022-03-22 | 株式会社半導体エネルギー研究所 | 燐光発光層用ホスト材料、有機化合物、発光素子、発光装置、電子機器および照明装置 |
| 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 |
| US10680184B2 (en) | 2016-07-11 | 2020-06-09 | 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 |
| KR101849747B1 (ko) | 2016-07-20 | 2018-05-31 | 주식회사 엘지화학 | 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자 |
| 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 |
| US11081658B2 (en) | 2016-10-03 | 2021-08-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11196010B2 (en) | 2016-10-03 | 2021-12-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11127906B2 (en) | 2016-10-03 | 2021-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11183642B2 (en) * | 2016-10-03 | 2021-11-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11189804B2 (en) | 2016-10-03 | 2021-11-30 | 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 |
| US11545636B2 (en) * | 2016-12-15 | 2023-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11548905B2 (en) | 2016-12-15 | 2023-01-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10490753B2 (en) | 2016-12-15 | 2019-11-26 | 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 |
| US20180190915A1 (en) * | 2017-01-03 | 2018-07-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11780865B2 (en) | 2017-01-09 | 2023-10-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11201298B2 (en) | 2017-01-09 | 2021-12-14 | 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 |
| US12089486B2 (en) | 2017-02-08 | 2024-09-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| 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 |
| US11139443B2 (en) | 2017-03-31 | 2021-10-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11276829B2 (en) | 2017-03-31 | 2022-03-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10777754B2 (en) | 2017-04-11 | 2020-09-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11038117B2 (en) | 2017-04-11 | 2021-06-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11101434B2 (en) | 2017-04-21 | 2021-08-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| 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 |
| 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 |
| US10944060B2 (en) | 2017-05-11 | 2021-03-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10822362B2 (en) | 2017-05-11 | 2020-11-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10840459B2 (en) | 2017-05-18 | 2020-11-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10934293B2 (en) | 2017-05-18 | 2021-03-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11038115B2 (en) | 2017-05-18 | 2021-06-15 | Universal Display Corporation | Organic electroluminescent materials and device |
| US10790455B2 (en) | 2017-05-18 | 2020-09-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10944062B2 (en) | 2017-05-18 | 2021-03-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10930862B2 (en) | 2017-06-01 | 2021-02-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| JP2019006763A (ja) | 2017-06-22 | 2019-01-17 | 株式会社半導体エネルギー研究所 | 有機化合物、発光素子、発光装置、電子機器、および照明装置 |
| US11758804B2 (en) | 2017-06-23 | 2023-09-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11814403B2 (en) | 2017-06-23 | 2023-11-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11725022B2 (en) | 2017-06-23 | 2023-08-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11678565B2 (en) | 2017-06-23 | 2023-06-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11608321B2 (en) | 2017-06-23 | 2023-03-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11552261B2 (en) | 2017-06-23 | 2023-01-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN109111486A (zh) | 2017-06-23 | 2019-01-01 | 环球展览公司 | 有机电致发光材料和装置 |
| US11832510B2 (en) | 2017-06-23 | 2023-11-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11802136B2 (en) | 2017-06-23 | 2023-10-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10968226B2 (en) | 2017-06-23 | 2021-04-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11495757B2 (en) | 2017-06-23 | 2022-11-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11174259B2 (en) | 2017-06-23 | 2021-11-16 | 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 |
| US11968883B2 (en) | 2017-07-26 | 2024-04-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11322691B2 (en) | 2017-07-26 | 2022-05-03 | 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 |
| US11508913B2 (en) | 2017-08-10 | 2022-11-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11349083B2 (en) | 2017-08-10 | 2022-05-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11744142B2 (en) | 2017-08-10 | 2023-08-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11910699B2 (en) | 2017-08-10 | 2024-02-20 | 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 |
| US11696492B2 (en) | 2017-09-07 | 2023-07-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11424420B2 (en) | 2017-09-07 | 2022-08-23 | 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 |
| US11183646B2 (en) | 2017-11-07 | 2021-11-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11910702B2 (en) | 2017-11-07 | 2024-02-20 | Universal Display Corporation | Organic electroluminescent devices |
| US11214587B2 (en) | 2017-11-07 | 2022-01-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| TWI785142B (zh) | 2017-11-14 | 2022-12-01 | 德商麥克專利有限公司 | 用於有機電子裝置之組成物 |
| 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 |
| US11233204B2 (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 |
| US12075690B2 (en) | 2017-12-14 | 2024-08-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11233205B2 (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 |
| US11515493B2 (en) | 2018-01-11 | 2022-11-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11271177B2 (en) | 2018-01-11 | 2022-03-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11845764B2 (en) | 2018-01-26 | 2023-12-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11367840B2 (en) | 2018-01-26 | 2022-06-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11542289B2 (en) | 2018-01-26 | 2023-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12029055B2 (en) | 2018-01-30 | 2024-07-02 | The University Of Southern California | OLED with hybrid emissive layer |
| US11180519B2 (en) | 2018-02-09 | 2021-11-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11342509B2 (en) | 2018-02-09 | 2022-05-24 | 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 |
| US11279722B2 (en) | 2018-03-12 | 2022-03-22 | 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 |
| US11165028B2 (en) | 2018-03-12 | 2021-11-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11557733B2 (en) | 2018-03-12 | 2023-01-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11882759B2 (en) | 2018-04-13 | 2024-01-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11390639B2 (en) | 2018-04-13 | 2022-07-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11616203B2 (en) | 2018-04-17 | 2023-03-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11753427B2 (en) | 2018-05-04 | 2023-09-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11515494B2 (en) * | 2018-05-04 | 2022-11-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11342513B2 (en) | 2018-05-04 | 2022-05-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11793073B2 (en) | 2018-05-06 | 2023-10-17 | Universal Display Corporation | Host materials for electroluminescent devices |
| US11459349B2 (en) * | 2018-05-25 | 2022-10-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11450822B2 (en) * | 2018-05-25 | 2022-09-20 | 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 |
| 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 |
| US11581497B2 (en) | 2018-07-09 | 2023-02-14 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
| US11753425B2 (en) * | 2018-07-11 | 2023-09-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| 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 |
| JP7498113B2 (ja) | 2018-09-20 | 2024-06-11 | 株式会社半導体エネルギー研究所 | 有機化合物、発光デバイス、発光装置、電子機器、および照明装置 |
| US11903305B2 (en) | 2018-09-24 | 2024-02-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11495752B2 (en) | 2018-10-08 | 2022-11-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11469383B2 (en) * | 2018-10-08 | 2022-10-11 | 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 |
| WO2020094542A1 (de) | 2018-11-06 | 2020-05-14 | Merck Patent Gmbh | 5,6-diphenyl-5,6-dihydro-dibenz[c,e][1,2]azaphosphorin- und 6-phenyl-6h-dibenzo[c,e][1,2]thiazin-5,5-dioxid-derivate und ähnliche verbindungen als organische elektrolumineszenzmaterialien für oleds |
| WO2020099307A1 (de) | 2018-11-15 | 2020-05-22 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
| 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 |
| US11706980B2 (en) | 2018-11-28 | 2023-07-18 | Universal Display Corporation | Host materials for electroluminescent devices |
| US11690285B2 (en) | 2018-11-28 | 2023-06-27 | Universal Display Corporation | Electroluminescent devices |
| US11672176B2 (en) | 2018-11-28 | 2023-06-06 | Universal Display Corporation | Host materials for electroluminescent devices |
| US11672165B2 (en) | 2018-11-28 | 2023-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11889708B2 (en) | 2019-11-14 | 2024-01-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11716899B2 (en) | 2018-11-28 | 2023-08-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11623936B2 (en) | 2018-12-11 | 2023-04-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11834459B2 (en) | 2018-12-12 | 2023-12-05 | Universal Display Corporation | Host materials for electroluminescent devices |
| US11737349B2 (en) | 2018-12-12 | 2023-08-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| KR20200073601A (ko) * | 2018-12-14 | 2020-06-24 | 엘지디스플레이 주식회사 | 유기 화합물, 이를 포함하는 유기발광다이오드 및 유기발광표시장치 |
| TW202039493A (zh) | 2018-12-19 | 2020-11-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
| 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 |
| US11325932B2 (en) | 2019-02-08 | 2022-05-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11370809B2 (en) | 2019-02-08 | 2022-06-28 | 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 |
| US11758807B2 (en) | 2019-02-22 | 2023-09-12 | 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 |
| 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 |
| US12082428B2 (en) | 2019-03-12 | 2024-09-03 | 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 |
| 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 |
| US11963438B2 (en) | 2019-03-26 | 2024-04-16 | The University Of Southern California | Organic electroluminescent materials and devices |
| US11639363B2 (en) | 2019-04-22 | 2023-05-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12075691B2 (en) | 2019-04-30 | 2024-08-27 | 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 |
| 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 |
| US11647667B2 (en) | 2019-06-14 | 2023-05-09 | Universal Display Corporation | Organic electroluminescent compounds and organic light emitting devices using the same |
| US12077550B2 (en) | 2019-07-02 | 2024-09-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| 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 |
| US11999886B2 (en) | 2019-09-26 | 2024-06-04 | 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 |
| KR20210084775A (ko) | 2019-12-27 | 2021-07-08 | 삼성전자주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
| 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 |
| US20220336759A1 (en) | 2020-01-28 | 2022-10-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11917900B2 (en) | 2020-01-28 | 2024-02-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11932660B2 (en) | 2020-01-29 | 2024-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12084465B2 (en) | 2020-02-24 | 2024-09-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20220352476A1 (en) * | 2020-02-28 | 2022-11-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12018035B2 (en) | 2020-03-23 | 2024-06-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11970508B2 (en) | 2020-04-22 | 2024-04-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12035613B2 (en) * | 2020-05-26 | 2024-07-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| KR102301612B1 (ko) * | 2020-06-22 | 2021-09-13 | (주)피엔에이치테크 | 유기발광 화합물 및 이를 포함하는 유기발광소자 |
| EP3937268A1 (en) | 2020-07-10 | 2022-01-12 | Universal Display Corporation | Plasmonic oleds and vertical dipole emitters |
| US20220045284A1 (en) * | 2020-08-05 | 2022-02-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12065451B2 (en) | 2020-08-19 | 2024-08-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20220112232A1 (en) * | 2020-10-02 | 2022-04-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
| 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 |
| CN113201244B (zh) * | 2021-04-30 | 2022-07-01 | 桂林理工大学 | 一种掺杂剂及其制备方法、应用、功能化乳胶漆 |
| 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 |
| KR20230110912A (ko) | 2022-01-17 | 2023-07-25 | 주식회사 에스켐 | 유기 발광 재료용 나프토 싸이오펜계 화합물의 제조 방법 |
| US20230292592A1 (en) | 2022-03-09 | 2023-09-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20230337516A1 (en) | 2022-04-18 | 2023-10-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| KR20230155968A (ko) * | 2022-05-02 | 2023-11-13 | 삼성디스플레이 주식회사 | 발광 소자 및 이를 포함한 전자 장치 |
| US20230389421A1 (en) | 2022-05-24 | 2023-11-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| EP4293001A1 (en) | 2022-06-08 | 2023-12-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20240016051A1 (en) | 2022-06-28 | 2024-01-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20240107880A1 (en) | 2022-08-17 | 2024-03-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20240180025A1 (en) | 2022-10-27 | 2024-05-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20240196730A1 (en) | 2022-10-27 | 2024-06-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20240188316A1 (en) | 2022-10-27 | 2024-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20240188319A1 (en) | 2022-10-27 | 2024-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20240188419A1 (en) | 2022-10-27 | 2024-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20240247017A1 (en) | 2022-12-14 | 2024-07-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11354281A (ja) * | 1998-04-10 | 1999-12-24 | Toray Ind Inc | 発光素子 |
| US20020064679A1 (en) * | 1997-12-25 | 2002-05-30 | Hitoshi Ishiskawa | Organic electroluminescent device having high efficient luminance |
| JP2004018665A (ja) * | 2002-06-17 | 2004-01-22 | Toyo Ink Mfg Co Ltd | 有機エレクトロルミネッセンス素子材料及びそれを使用した有機エレクトロルミネッセンス素子 |
| US20060088728A1 (en) * | 2004-10-22 | 2006-04-27 | Raymond Kwong | Arylcarbazoles as hosts in PHOLEDs |
| US20070072002A1 (en) * | 2005-09-23 | 2007-03-29 | Myeong-Suk Kim | Organic light-emitting compound and organic light-emitting device containing the same |
| US20070141387A1 (en) * | 2005-12-15 | 2007-06-21 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescence device and electroluminescence device employing the same |
| WO2007069569A1 (ja) * | 2005-12-15 | 2007-06-21 | Idemitsu Kosan 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 |
Family Cites Families (155)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4772940A (en) | 1985-05-22 | 1988-09-20 | Regents Of The University Of California | Polymer having isothianaphthene structure and electrochromic display |
| US4769292A (en) * | 1987-03-02 | 1988-09-06 | Eastman Kodak Company | Electroluminescent device with modified thin film luminescent zone |
| GB8909011D0 (en) * | 1989-04-20 | 1989-06-07 | Friend Richard H | Electroluminescent devices |
| US5061569A (en) | 1990-07-26 | 1991-10-29 | Eastman Kodak Company | Electroluminescent device with organic electroluminescent medium |
| JPH05109485A (ja) * | 1991-10-15 | 1993-04-30 | Ricoh Co Ltd | 電界発光素子 |
| DE69412567T2 (de) | 1993-11-01 | 1999-02-04 | Hodogaya Chemical Co., Ltd., Tokio/Tokyo | Aminverbindung und sie enthaltende Elektrolumineszenzvorrichtung |
| US5703436A (en) * | 1994-12-13 | 1997-12-30 | The Trustees Of Princeton University | Transparent contacts for organic devices |
| US5707745A (en) * | 1994-12-13 | 1998-01-13 | The Trustees Of Princeton University | Multicolor organic light emitting devices |
| DE19517208A1 (de) * | 1995-05-11 | 1996-11-14 | Basf Ag | Derivate des Triphenylens |
| US6939625B2 (en) | 1996-06-25 | 2005-09-06 | Nôrthwestern University | Organic light-emitting diodes and methods for assembly and enhanced charge injection |
| US5844363A (en) * | 1997-01-23 | 1998-12-01 | The Trustees Of Princeton Univ. | Vacuum deposited, non-polymeric flexible organic light emitting devices |
| US6091195A (en) * | 1997-02-03 | 2000-07-18 | The Trustees Of Princeton University | Displays having mesa pixel configuration |
| US5834893A (en) * | 1996-12-23 | 1998-11-10 | The Trustees Of Princeton University | High efficiency organic light emitting devices with light directing structures |
| US6013982A (en) * | 1996-12-23 | 2000-01-11 | The Trustees Of Princeton University | Multicolor display devices |
| US6303238B1 (en) * | 1997-12-01 | 2001-10-16 | The Trustees Of Princeton University | OLEDs doped with phosphorescent compounds |
| US6337102B1 (en) * | 1997-11-17 | 2002-01-08 | The Trustees Of Princeton University | Low pressure vapor phase deposition of organic thin films |
| JP3424812B2 (ja) * | 1997-12-25 | 2003-07-07 | 日本電気株式会社 | 有機エレクトロルミネッセンス素子 |
| US6087196A (en) * | 1998-01-30 | 2000-07-11 | The Trustees Of Princeton University | Fabrication of organic semiconductor devices using ink jet printing |
| US6528187B1 (en) | 1998-09-08 | 2003-03-04 | Fuji Photo Film Co., Ltd. | Material for luminescence element and luminescence element using the same |
| US6097147A (en) * | 1998-09-14 | 2000-08-01 | The Trustees Of Princeton University | Structure for high efficiency electroluminescent device |
| US6830828B2 (en) | 1998-09-14 | 2004-12-14 | The Trustees Of Princeton University | Organometallic complexes as phosphorescent emitters in organic LEDs |
| JP2000156289A (ja) * | 1998-11-18 | 2000-06-06 | Toyota Central Res & Dev Lab Inc | 有機電界発光素子 |
| JP2000273055A (ja) * | 1999-03-25 | 2000-10-03 | Idemitsu Kosan Co Ltd | ジスチリルアリーレ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 |
| US6294398B1 (en) * | 1999-11-23 | 2001-09-25 | The Trustees Of Princeton University | Method for patterning devices |
| US6458475B1 (en) | 1999-11-24 | 2002-10-01 | The Trustee Of Princeton University | Organic light emitting diode having a blue phosphorescent molecule as an emitter |
| KR100377321B1 (ko) | 1999-12-31 | 2003-03-26 | 주식회사 엘지화학 | 피-형 반도체 성질을 갖는 유기 화합물을 포함하는 전기소자 |
| JP2001196182A (ja) * | 2000-01-14 | 2001-07-19 | Toray Ind Inc | 発光素子 |
| US20020121638A1 (en) | 2000-06-30 | 2002-09-05 | Vladimir Grushin | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
| JP2002050860A (ja) | 2000-08-04 | 2002-02-15 | Toray Eng Co Ltd | 実装方法および実装装置 |
| WO2002015645A1 (en) | 2000-08-11 | 2002-02-21 | The Trustees Of Princeton University | Organometallic compounds and emission-shifting organic electrophosphorescence |
| US6579630B2 (en) | 2000-12-07 | 2003-06-17 | Canon Kabushiki Kaisha | Deuterated semiconducting organic compounds used for opto-electronic devices |
| JP3812730B2 (ja) | 2001-02-01 | 2006-08-23 | 富士写真フイルム株式会社 | 遷移金属錯体及び発光素子 |
| JP4307000B2 (ja) | 2001-03-08 | 2009-08-05 | キヤノン株式会社 | 金属配位化合物、電界発光素子及び表示装置 |
| JP4310077B2 (ja) | 2001-06-19 | 2009-08-05 | キヤノン株式会社 | 金属配位化合物及び有機発光素子 |
| ATE431970T1 (de) | 2001-06-20 | 2009-06-15 | Showa Denko Kk | Licht emittierendes material und organische leuchtdiode |
| US7071615B2 (en) * | 2001-08-20 | 2006-07-04 | Universal Display Corporation | Transparent electrodes |
| US7250226B2 (en) | 2001-08-31 | 2007-07-31 | Nippon Hoso Kyokai | Phosphorescent compound, a phosphorescent composition and an organic light-emitting device |
| US7431968B1 (en) * | 2001-09-04 | 2008-10-07 | The Trustees Of Princeton University | Process and apparatus for organic vapor jet deposition |
| JP2003109763A (ja) * | 2001-09-28 | 2003-04-11 | Canon Inc | 有機発光素子 |
| GB2380191A (en) | 2001-09-28 | 2003-04-02 | Sharp Kk | Benzofuran compounds their preparation and their use in electroluminescent and photovoltaic devices |
| US6835469B2 (en) | 2001-10-17 | 2004-12-28 | The University Of Southern California | Phosphorescent compounds and devices comprising the same |
| US7166368B2 (en) | 2001-11-07 | 2007-01-23 | E. I. Du Pont De Nemours And Company | Electroluminescent platinum compounds and devices made with such compounds |
| US6863997B2 (en) | 2001-12-28 | 2005-03-08 | The Trustees Of Princeton University | White light emitting OLEDs from combined monomer and aggregate emission |
| KR100691543B1 (ko) | 2002-01-18 | 2007-03-09 | 주식회사 엘지화학 | 새로운 전자 수송용 물질 및 이를 이용한 유기 발광 소자 |
| US6878975B2 (en) | 2002-02-08 | 2005-04-12 | Agilent Technologies, Inc. | Polarization field enhanced tunnel structures |
| US20030230980A1 (en) * | 2002-06-18 | 2003-12-18 | Forrest Stephen R | Very low voltage, high efficiency phosphorescent oled in a p-i-n structure |
| JP3964751B2 (ja) | 2002-07-15 | 2007-08-22 | 日本電信電話株式会社 | ネットワーク品質推定制御方式 |
| US6916554B2 (en) * | 2002-11-06 | 2005-07-12 | The University Of Southern California | Organic light emitting materials and devices |
| US7189989B2 (en) | 2002-08-22 | 2007-03-13 | Fuji Photo Film Co., Ltd. | Light emitting element |
| CN100439469C (zh) | 2002-08-27 | 2008-12-03 | 富士胶片株式会社 | 有机金属配位化合物、有机el元件及有机el显示器 |
| TW593624B (en) * | 2002-10-16 | 2004-06-21 | Univ Tsinghua | Aromatic compounds and organic LED |
| US6687266B1 (en) | 2002-11-08 | 2004-02-03 | Universal Display Corporation | Organic light emitting materials and devices |
| JP4365196B2 (ja) | 2002-12-27 | 2009-11-18 | 富士フイルム株式会社 | 有機電界発光素子 |
| JP4365199B2 (ja) | 2002-12-27 | 2009-11-18 | 富士フイルム株式会社 | 有機電界発光素子 |
| CN100387607C (zh) | 2003-03-24 | 2008-05-14 | 南加利福尼亚大学 | Ir的苯基-吡唑配合物 |
| US7090928B2 (en) | 2003-04-01 | 2006-08-15 | The University Of Southern California | Binuclear compounds |
| EP1717291A3 (de) | 2003-04-15 | 2007-03-21 | Merck Patent GmbH | Mischungen von organischen, zur Emission befähigten Halbleitern und Maxtrixmaterialien, deren Verwendung und diese Mischungen enthaltende Elektronikbauteile |
| US7029765B2 (en) | 2003-04-22 | 2006-04-18 | Universal Display Corporation | Organic light emitting devices having reduced pixel shrinkage |
| US20060186791A1 (en) | 2003-05-29 | 2006-08-24 | Osamu Yoshitake | Organic electroluminescent element |
| JP2005011610A (ja) | 2003-06-18 | 2005-01-13 | Nippon Steel Chem Co Ltd | 有機電界発光素子 |
| US20050025993A1 (en) | 2003-07-25 | 2005-02-03 | Thompson Mark E. | Materials and structures for enhancing the performance of organic light emitting devices |
| JP4392206B2 (ja) * | 2003-07-30 | 2009-12-24 | 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 |
| JP4703139B2 (ja) * | 2003-08-04 | 2011-06-15 | 富士フイルム株式会社 | 有機電界発光素子 |
| TWI390006B (zh) | 2003-08-07 | 2013-03-21 | Nippon Steel Chemical Co | Organic EL materials with aluminum clamps |
| DE10338550A1 (de) | 2003-08-19 | 2005-03-31 | Basf Ag | Übergangsmetallkomplexe mit Carbenliganden als Emitter für organische Licht-emittierende Dioden (OLEDs) |
| US20060269780A1 (en) | 2003-09-25 | 2006-11-30 | Takayuki Fukumatsu | Organic electroluminescent device |
| JP4822687B2 (ja) | 2003-11-21 | 2011-11-24 | 富士フイルム株式会社 | 有機電界発光素子 |
| KR101118447B1 (ko) | 2004-01-13 | 2012-03-06 | 엔엑스피 비 브이 | 멀티 칩 시스템 및 이 시스템을 테스트하는 방법 |
| US7332232B2 (en) | 2004-02-03 | 2008-02-19 | Universal Display Corporation | OLEDs utilizing multidentate ligand systems |
| JP4906235B2 (ja) * | 2004-03-10 | 2012-03-28 | 富士フイルム株式会社 | 有機電界発光素子 |
| KR100834327B1 (ko) | 2004-03-11 | 2008-06-02 | 미쓰비시 가가꾸 가부시키가이샤 | 전하 수송막용 조성물 및 이온 화합물, 이를 이용한 전하수송막 및 유기 전계 발광 장치, 및 유기 전계 발광 장치의제조 방법 및 전하 수송막의 제조 방법 |
| TW200531592A (en) | 2004-03-15 | 2005-09-16 | Nippon Steel Chemical Co | Organic electroluminescent device |
| JP4869565B2 (ja) | 2004-04-23 | 2012-02-08 | 富士フイルム株式会社 | 有機電界発光素子 |
| US7279704B2 (en) * | 2004-05-18 | 2007-10-09 | The University Of Southern California | Complexes with tridentate ligands |
| US7534505B2 (en) | 2004-05-18 | 2009-05-19 | The University Of Southern California | Organometallic compounds for use in electroluminescent devices |
| US7393599B2 (en) | 2004-05-18 | 2008-07-01 | The University Of Southern California | Luminescent compounds with carbene ligands |
| US7491823B2 (en) | 2004-05-18 | 2009-02-17 | The University Of Southern California | Luminescent compounds with carbene ligands |
| US7445855B2 (en) | 2004-05-18 | 2008-11-04 | The University Of Southern California | Cationic metal-carbene complexes |
| US7154114B2 (en) | 2004-05-18 | 2006-12-26 | Universal Display Corporation | Cyclometallated iridium carbene complexes for use as hosts |
| WO2005123873A1 (ja) | 2004-06-17 | 2005-12-29 | 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 |
| JP5000496B2 (ja) | 2004-06-28 | 2012-08-15 | チバ ホールディング インコーポレーテッド | トリアゾールとベンゾトリアゾールのエレクトロルミネセンス金属錯体 |
| US20060008670A1 (en) | 2004-07-06 | 2006-01-12 | Chun Lin | Organic light emitting materials and devices |
| US7504657B2 (en) | 2004-07-23 | 2009-03-17 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, display and illuminator |
| JP4883955B2 (ja) * | 2004-07-30 | 2012-02-22 | 国立大学法人大阪大学 | 有機半導体およびそれを用いた電子機器 |
| JP4683886B2 (ja) * | 2004-09-13 | 2011-05-18 | 大日本印刷株式会社 | チオフェン誘導体および有機エレクトロルミネッセンス素子 |
| JP2006143845A (ja) * | 2004-11-18 | 2006-06-08 | Konica Minolta Holdings Inc | 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、照明装置及び表示装置 |
| DE102004057072A1 (de) | 2004-11-25 | 2006-06-01 | Basf Ag | Verwendung von Übergangsmetall-Carbenkomplexen in organischen Licht-emittierenden Dioden (OLEDs) |
| JP4677221B2 (ja) * | 2004-11-26 | 2011-04-27 | キヤノン株式会社 | 有機発光素子 |
| JP2008526766A (ja) | 2004-12-30 | 2008-07-24 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 有機金属錯体 |
| US8377571B2 (en) | 2005-02-04 | 2013-02-19 | Konica Minolta Holdings, Inc. | Material for organic electroluminescence element, organic electroluminescence element, display device and lighting device |
| KR100803125B1 (ko) | 2005-03-08 | 2008-02-14 | 엘지전자 주식회사 | 적색 인광 화합물 및 이를 사용한 유기전계발광소자 |
| WO2006098120A1 (ja) | 2005-03-16 | 2006-09-21 | 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 |
| DE102005014284A1 (de) | 2005-03-24 | 2006-09-28 | Basf Ag | Verwendung von Verbindungen, welche aromatische oder heteroaromatische über Carbonyl-Gruppen enthaltende Gruppen verbundene Ringe enthalten, als Matrixmaterialien in organischen Leuchtdioden |
| JPWO2006103874A1 (ja) | 2005-03-29 | 2008-09-04 | 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 |
| GB2439030B (en) * | 2005-04-18 | 2011-03-02 | Konica Minolta Holdings Inc | Organic electroluminescent device, display and illuminating device |
| US7807275B2 (en) | 2005-04-21 | 2010-10-05 | Universal Display Corporation | Non-blocked phosphorescent OLEDs |
| US9051344B2 (en) | 2005-05-06 | 2015-06-09 | Universal Display Corporation | Stability OLED materials and devices |
| JP4533796B2 (ja) | 2005-05-06 | 2010-09-01 | 富士フイルム株式会社 | 有機電界発光素子 |
| DE602006011734D1 (de) | 2005-05-30 | 2010-03-04 | Basf Se | Elektrolumineszenz-gerät |
| EP1888708B1 (en) * | 2005-05-31 | 2012-11-21 | Universal Display Corporation | Triphenylene hosts in phosphorescent light emitting diodes |
| US8709614B2 (en) | 2005-06-07 | 2014-04-29 | Nippon Steel & Sumikin Chemical Co., Ltd. | Organic metal complex and its use in organic electroluminescent device |
| JP4865258B2 (ja) * | 2005-06-21 | 2012-02-01 | キヤノン株式会社 | １，８−ナフチリジン化合物及びそれを用いた有機発光素子 |
| 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 |
| WO2007002683A2 (en) | 2005-06-27 | 2007-01-04 | E. I. Du Pont De Nemours And Company | Electrically conductive polymer compositions |
| WO2007004380A1 (ja) | 2005-07-01 | 2007-01-11 | 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 |
| JP2007027356A (ja) * | 2005-07-15 | 2007-02-01 | Toyo Ink Mfg Co Ltd | 有機エレクトロルミネッセンス素子用材料 |
| KR101418840B1 (ko) * | 2005-09-05 | 2014-07-11 | 제이엔씨 주식회사 | 전자 수송 재료 및 이것을 이용한 유기 전계발광 소자 |
| WO2007028417A1 (en) | 2005-09-07 | 2007-03-15 | Technische Universität Braunschweig | Triplett emitter having condensed five-membered rings |
| JP4887731B2 (ja) | 2005-10-26 | 2012-02-29 | 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 |
| JP4947955B2 (ja) * | 2005-11-04 | 2012-06-06 | 三洋電機株式会社 | ジベンゾチオフェ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 |
| JPWO2007063796A1 (ja) | 2005-12-01 | 2009-05-07 | 新日鐵化学株式会社 | 有機電界発光素子 |
| US7993760B2 (en) | 2005-12-01 | 2011-08-09 | Nippon Steel Chemical Co., Ltd. | Compound for use in organic electroluminescent device and organic electroluminescent device |
| JP4972938B2 (ja) * | 2006-01-12 | 2012-07-11 | 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 |
| KR20160030582A (ko) | 2006-02-10 | 2016-03-18 | 유니버셜 디스플레이 코포레이션 | 시클로금속화 이미다조[1,2-ｆ]페난트리딘 및 디이미다조[1,2-ａ:1'',2''-ｃ]퀴나졸린 리간드, 및 이의 등전자성 및 벤즈고리화된 유사체의 금속 착체 |
| US8142909B2 (en) | 2006-02-10 | 2012-03-27 | Universal Display Corporation | Blue phosphorescent imidazophenanthridine materials |
| JP4823730B2 (ja) | 2006-03-20 | 2011-11-24 | 新日鐵化学株式会社 | 発光層化合物及び有機電界発光素子 |
| EP2011790B1 (en) | 2006-04-26 | 2016-06-29 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative, and organic electroluminescence element using the same |
| WO2007132678A1 (ja) | 2006-05-11 | 2007-11-22 | Idemitsu Kosan Co., Ltd. | 有機エレクトロルミネッセンス素子 |
| CN101461074B (zh) | 2006-06-02 | 2011-06-15 | 出光兴产株式会社 | 有机电致发光元件用材料及使用了它的有机电致发光元件 |
| KR20090040896A (ko) | 2006-08-23 | 2009-04-27 | 이데미쓰 고산 가부시키가이샤 | 방향족 아민 유도체 및 이들을 이용한 유기 전기발광 소자 |
| JP5589251B2 (ja) | 2006-09-21 | 2014-09-17 | 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材料 |
| EP2080762B1 (en) | 2006-11-09 | 2016-09-14 | Nippon Steel & Sumikin Chemical Co., Ltd. | Compound for organic electroluminescent device and organic electroluminescent device |
| FR2908880B1 (fr) | 2006-11-21 | 2009-01-16 | Centre Nat Rech Scient | Dispositif de detection d'interferences monolithique integre |
| KR101347519B1 (ko) | 2006-11-24 | 2014-01-03 | 이데미쓰 고산 가부시키가이샤 | 방향족 아민 유도체 및 그것을 이용한 유기 전기발광 소자 |
| US8119255B2 (en) | 2006-12-08 | 2012-02-21 | Universal Display Corporation | Cross-linkable iridium complexes and organic light-emitting devices using the same |
| EP2097938B1 (en) | 2006-12-28 | 2019-07-17 | Universal Display Corporation | Long lifetime phosphorescent organic light emitting device (oled) structures |
| WO2008101842A1 (en) | 2007-02-23 | 2008-08-28 | Basf Se | Electroluminescent metal complexes with benzotriazoles |
| CN101687893B (zh) | 2007-04-26 | 2014-01-22 | 巴斯夫欧洲公司 | 含有吩噻嗪s-氧化物或吩噻嗪s,s-二氧化物基团的硅烷及其在oled中的用途 |
| EP2170911B1 (en) | 2007-06-22 | 2018-11-28 | UDC Ireland Limited | Light emitting cu(i) complexes |
| WO2009003898A1 (de) | 2007-07-05 | 2009-01-08 | Basf Se | Organische leuchtdioden enthaltend carben-übergangsmetall-komplex-emitter und mindestens eine verbindung ausgewählt aus disilylcarbazolen; disilyldibenzofuranen, disilyldibenzothiophenen, disilyldibenzophospholen, disilyldibenzothiophen-s-oxiden und disilyldibenzothiophen-s,s-dioxiden |
| JP5473600B2 (ja) | 2007-07-07 | 2014-04-16 | 出光興産株式会社 | クリセ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 |
| US8021574B2 (en) | 2007-07-07 | 2011-09-20 | Idemitsu Kosan Co., Ltd. | Naphthalene derivative, material for organic electroluminescence device, and organic electroluminescence device using the same |
| US20090045731A1 (en) | 2007-07-07 | 2009-02-19 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and material for organic electroluminescence device |
| WO2009008205A1 (ja) | 2007-07-07 | 2009-01-15 | Idemitsu Kosan Co., Ltd. | 有機エレクトロルミネッセンス素子および有機エレクトロルミネッセンス素子用材料 |
| US8779655B2 (en) | 2007-07-07 | 2014-07-15 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and material for organic electroluminescence device |
| US8114530B2 (en) | 2007-07-10 | 2012-02-14 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescence device and organic electroluminescence device utilizing the same |
| US8080658B2 (en) | 2007-07-10 | 2011-12-20 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescent element and organic electroluminescent element employing the same |
| EP2173811A1 (en) | 2007-07-27 | 2010-04-14 | E. I. du Pont de Nemours and Company | Aqueous dispersions of electrically conducting polymers containing inorganic nanoparticles |
| KR20160086983A (ko) * | 2007-08-08 | 2016-07-20 | 유니버셜 디스플레이 코포레이션 | 트리페닐렌기를 포함하는 벤조 융합 티오펜 또는 벤조 융합 푸란 화합물 |
| JP2009040728A (ja) | 2007-08-09 | 2009-02-26 | Canon Inc | 有機金属錯体及びこれを用いた有機発光素子 |
| DE602007010624D1 (de) | 2007-09-07 | 2010-12-30 | Milano Politecnico | Phasenwechsel-Speichervorrichtung für Multibit-Speicherung |
| KR101642030B1 (ko) | 2007-10-17 | 2016-07-25 | 바스프 에스이 | 가교된 카르벤 리간드를 포함하는 전이 금속 착물 및 이의 용도 |
| US20090101870A1 (en) | 2007-10-22 | 2009-04-23 | E. I. Du Pont De Nemours And Company | Electron transport bi-layers and devices made with such bi-layers |
| US7914908B2 (en) | 2007-11-02 | 2011-03-29 | Global Oled Technology Llc | Organic electroluminescent device having an azatriphenylene derivative |
| DE102007053771A1 (de) | 2007-11-12 | 2009-05-14 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtungen |
| EP2216313B1 (en) | 2007-11-15 | 2013-02-20 | Idemitsu Kosan Co., Ltd. | Benzochrysene derivative and organic electroluminescent device using the same |
| WO2009066776A1 (ja) | 2007-11-21 | 2009-05-28 | Moriyama Giken Co., Ltd. | 半凝固金属の成型装置および成型方法 |
| JP5270571B2 (ja) | 2007-11-22 | 2013-08-21 | 出光興産株式会社 | 有機ｅｌ素子 |
| EP2221897A4 (en) | 2007-11-22 | 2012-08-08 | Idemitsu Kosan Co | ORGANIC EL ELEMENT AND ORGANIC EL-MATERIAL SOLUTION |
| WO2009073245A1 (en) | 2007-12-06 | 2009-06-11 | Universal Display Corporation | Light-emitting organometallic complexes |
| US8221905B2 (en) | 2007-12-28 | 2012-07-17 | Universal Display Corporation | Carbazole-containing materials in phosphorescent light emitting diodes |
| WO2009085344A2 (en) | 2007-12-28 | 2009-07-09 | Universal Display Corporation | Dibenzothiophene-containing materials in phosphorescent light emitting diodes |
| US8471248B2 (en) | 2008-02-12 | 2013-06-25 | Basf Se | Electroluminiscent metal complexes with dibenzo[f,h] quinoxalines |
| JP5359792B2 (ja) | 2009-11-02 | 2013-12-04 | セイコーエプソン株式会社 | 例外処理管理装置、例外処理管理装置の制御方法およびプログラム |
| US8968887B2 (en) * | 2010-04-28 | 2015-03-03 | Universal Display Corporation | Triphenylene-benzofuran/benzothiophene/benzoselenophene compounds with substituents joining to form fused rings |
-
2008
- 2008-08-07 KR KR1020167018663A patent/KR20160086983A/ko not_active Application Discontinuation
- 2008-08-07 KR KR1020107005152A patent/KR101630883B1/ko active IP Right Grant
- 2008-08-07 KR KR1020157008181A patent/KR101787850B1/ko active IP Right Grant
- 2008-08-07 US US12/672,198 patent/US8367850B2/en active Active
- 2008-08-07 TW TW104127754A patent/TWI531567B/zh active
- 2008-08-07 TW TW104137065A patent/TWI551594B/zh active
- 2008-08-07 CN CN201410503620.7A patent/CN104311533B/zh active Active
- 2008-08-07 JP JP2010520310A patent/JP6009144B2/ja active Active
- 2008-08-07 CN CN200880106949.2A patent/CN101827834B/zh active Active
- 2008-08-07 CN CN201510646336.XA patent/CN105367544B/zh active Active
- 2008-08-07 WO PCT/US2008/072499 patent/WO2009021126A2/en active Application Filing
- 2008-08-07 EP EP16197588.3A patent/EP3159333B1/en active Active
- 2008-08-07 EP EP08797391.3A patent/EP2185532B1/en active Active
- 2008-08-07 KR KR1020147023913A patent/KR101565724B1/ko active IP Right Grant
- 2008-08-07 TW TW097130183A patent/TWI511964B/zh active
-
2012
- 2012-12-14 US US13/714,872 patent/US8822708B2/en active Active
-
2014
- 2014-01-23 JP JP2014010322A patent/JP6261991B2/ja active Active
- 2014-07-18 US US14/335,076 patent/US9153786B2/en active Active
- 2014-09-19 JP JP2014191683A patent/JP6062903B2/ja active Active
-
2015
- 2015-08-28 US US14/838,450 patent/US9577200B2/en active Active
-
2016
- 2016-03-15 JP JP2016050615A patent/JP6144380B2/ja active Active
-
2017
- 2017-01-09 US US15/401,438 patent/US9997727B2/en active Active
- 2017-07-24 JP JP2017142948A patent/JP6734231B2/ja active Active
-
2018
- 2018-05-11 US US15/977,452 patent/US10374171B2/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020064679A1 (en) * | 1997-12-25 | 2002-05-30 | Hitoshi Ishiskawa | Organic electroluminescent device having high efficient luminance |
| JPH11354281A (ja) * | 1998-04-10 | 1999-12-24 | Toray Ind Inc | 発光素子 |
| JP2004018665A (ja) * | 2002-06-17 | 2004-01-22 | Toyo Ink Mfg Co Ltd | 有機エレクトロルミネッセンス素子材料及びそれを使用した有機エレクトロルミネッセンス素子 |
| US20060088728A1 (en) * | 2004-10-22 | 2006-04-27 | Raymond Kwong | Arylcarbazoles as hosts in PHOLEDs |
| US20070072002A1 (en) * | 2005-09-23 | 2007-03-29 | Myeong-Suk Kim | Organic light-emitting compound and organic light-emitting device containing the same |
| US20070141387A1 (en) * | 2005-12-15 | 2007-06-21 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescence device and electroluminescence device employing the same |
| WO2007069569A1 (ja) * | 2005-12-15 | 2007-06-21 | Idemitsu Kosan 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 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112409416A (zh) * | 2019-08-21 | 2021-02-26 | 环球展览公司 | 有机电致发光材料和装置 |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101827834B (zh) | 含苯并[9，10]菲的苯并稠合的噻吩或苯并稠合的呋喃化合物 | |
| JP6506243B2 (ja) | 有機セレン材料および有機発光デバイス内でのその使用 | |
| CN103788113B (zh) | 用于pholed的具有氮杂-二苯并噻吩或氮杂-二苯并呋喃核的新材料 | |
| CN109134348A (zh) | 一种咔唑类化合物及其有机发光器件 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |