US20190372016A1 - Compound and organic electronic device using the same - Google Patents
Compound and organic electronic device using the same Download PDFInfo
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- US20190372016A1 US20190372016A1 US16/429,594 US201916429594A US2019372016A1 US 20190372016 A1 US20190372016 A1 US 20190372016A1 US 201916429594 A US201916429594 A US 201916429594A US 2019372016 A1 US2019372016 A1 US 2019372016A1
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 106
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 133
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 3
- 239000010410 layer Substances 0.000 claims description 97
- 125000000524 functional group Chemical group 0.000 claims description 57
- -1 isobenzothiophenyl group Chemical group 0.000 claims description 33
- 239000012044 organic layer Substances 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 238000002347 injection Methods 0.000 claims description 22
- 239000007924 injection Substances 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 230000005525 hole transport Effects 0.000 claims description 15
- 230000000903 blocking effect Effects 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 229910052805 deuterium Inorganic materials 0.000 claims description 11
- 125000004431 deuterium atom Chemical group 0.000 claims description 11
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 claims description 8
- ATYBXHSAIOKLMG-UHFFFAOYSA-N oxepin Chemical group O1C=CC=CC=C1 ATYBXHSAIOKLMG-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 7
- 125000005104 aryl silyl group Chemical group 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 7
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 6
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 6
- 125000006267 biphenyl group Chemical group 0.000 claims description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 6
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 claims description 6
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000005561 phenanthryl group Chemical group 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000005390 cinnolyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 4
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims description 4
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 4
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000004306 triazinyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 2
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 2
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 0 Ic1nc(-c2ccccn2)nc(-c(cc2)ccc2-c2c(ccc(-c3cc(-c4cc(C5=CC(c6cccc(-c7cccnc7)c6)=I*C(I)=I5)ccc4)ccc3)c3)c3ccc2)c1 Chemical compound Ic1nc(-c2ccccn2)nc(-c(cc2)ccc2-c2c(ccc(-c3cc(-c4cc(C5=CC(c6cccc(-c7cccnc7)c6)=I*C(I)=I5)ccc4)ccc3)c3)c3ccc2)c1 0.000 description 216
- 239000000543 intermediate Substances 0.000 description 137
- 239000000376 reactant Substances 0.000 description 65
- 239000000463 material Substances 0.000 description 49
- 239000000126 substance Substances 0.000 description 33
- 238000003786 synthesis reaction Methods 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 24
- 235000013350 formula milk Nutrition 0.000 description 23
- 230000000052 comparative effect Effects 0.000 description 18
- 238000000434 field desorption mass spectrometry Methods 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 10
- 230000037361 pathway Effects 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000012265 solid product Substances 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229940125904 compound 1 Drugs 0.000 description 7
- 229940125782 compound 2 Drugs 0.000 description 7
- 238000012986 modification Methods 0.000 description 7
- 230000004048 modification Effects 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 4
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 4
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229940125797 compound 12 Drugs 0.000 description 4
- 229940125898 compound 5 Drugs 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 230000007246 mechanism Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
- 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 4
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 3
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- PAPMWUVZKKBIDC-UHFFFAOYSA-N CC1(C)c(cc2c3cccc(-c4nc(-c5cc(-c6ccccc6)ccc5)nc(-c5cccc(-c6ccccc6)c5)n4)c3ccc2c2)c2-c2ccccc12 Chemical compound CC1(C)c(cc2c3cccc(-c4nc(-c5cc(-c6ccccc6)ccc5)nc(-c5cccc(-c6ccccc6)c5)n4)c3ccc2c2)c2-c2ccccc12 PAPMWUVZKKBIDC-UHFFFAOYSA-N 0.000 description 3
- FAAULHKHLIESBO-UHFFFAOYSA-N CC1(C)c2cc3c(ccc(-c4nc(-c5cc(-c6ccccc6)ccc5)nc(-c5cccc(-c6ccccc6)c5)n4)c4)c4ccc3cc2-c2ccccc12 Chemical compound CC1(C)c2cc3c(ccc(-c4nc(-c5cc(-c6ccccc6)ccc5)nc(-c5cccc(-c6ccccc6)c5)n4)c4)c4ccc3cc2-c2ccccc12 FAAULHKHLIESBO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYVIOMJSKUGJLV-UHFFFAOYSA-N [Ir+2] Chemical compound [Ir+2] VYVIOMJSKUGJLV-UHFFFAOYSA-N 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 229940125773 compound 10 Drugs 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- RFDGVZHLJCKEPT-UHFFFAOYSA-N tris(2,4,6-trimethyl-3-pyridin-3-ylphenyl)borane Chemical compound CC1=C(B(C=2C(=C(C=3C=NC=CC=3)C(C)=CC=2C)C)C=2C(=C(C=3C=NC=CC=3)C(C)=CC=2C)C)C(C)=CC(C)=C1C1=CC=CN=C1 RFDGVZHLJCKEPT-UHFFFAOYSA-N 0.000 description 3
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 2
- DMDPAJOXRYGXCB-UHFFFAOYSA-N (9,9-dimethylfluoren-2-yl)boronic acid Chemical compound C1=C(B(O)O)C=C2C(C)(C)C3=CC=CC=C3C2=C1 DMDPAJOXRYGXCB-UHFFFAOYSA-N 0.000 description 2
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Images
Classifications
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
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- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
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- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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Definitions
- the present invention relates to a novel compound and an organic electronic device using the same, more particularly to a novel compound as an electron transport material for an electron transport layer and an organic electronic device using the same.
- organic electronic devices that make use of organic materials have been energetically developed.
- organic electronic devices include organic light emitting devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors.
- OLEDs organic light emitting devices
- organic phototransistors organic phototransistors
- organic photovoltaic cells organic photovoltaic cells
- organic photodetectors organic photodetectors
- OLED was initially invented and proposed by Eastman Kodak Company through a vacuum evaporation method.
- Dr. Ching M. Tang and Steven Van Slyke of Kodak Company deposited an electron transport material such as tris(8-hydroxyquinoline)aluminum(III) (abbreviated as Alq 3 ) on a transparent indium tin oxide glass (abbreviated as ITO glass) formed with a hole transport layer of organic aromatic diamine thereon, and subsequently deposited a metal electrode onto an electron transport layer to complete the fabrication of the OLED.
- OLEDs have attracted lots of attention due to their numerous advantages, such as fast response speed, light weight, compactness, wide viewing angle, high brightness, higher contrast ratio, no need of backlight, and low power consumption. However, the OLEDs still have the problems such as short lifespan.
- a modified OLED 1 may have a structure of a substrate 11 , an anode 12 , a hole injection layer 13 (abbreviated as HIL), a hole transport layer 14 (abbreviated as HTL), an emission layer 15 (abbreviated as EL), an electron transport layer 16 (abbreviated as ETL), an electron injection layer 17 (abbreviated as EIL), and a cathode 18 stacked in sequence.
- HIL hole injection layer 13
- HTL hole transport layer 14
- EL emission layer 15
- ETL electron transport layer 16
- EIL electron injection layer 17
- ETL for OLEDs examples include 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 3,3′-[5′-[3-(3-pyridinyl)phenyl][1,1′: 3′,1′′-terphenyl]-3,3′′-diyl]bispyridine (TmPyPb), 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), tris(2,4,6-trimethyl-3-(pyridin-3-yl)phenyl)borane (3TPYMB), 1,3-bis(3,5-dipyrid-3-yl-phenyl)benzene (BmPyPb), and 9,10-bis(3-(pyridin-3-yl)phenyl)anthracene (DPyPA).
- BCP 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline
- the present invention provides a novel compound to mitigate or obviate the problems in the prior art.
- An objective of the present invention is to provide a novel compound useful for an organic electronic device.
- Another objective of the present invention is to provide an organic electronic device using the novel compound, so as to prolong the lifespan of the organic electronic device.
- a 1 and A 2 each represent a carbon atom; *1 is bonded to one of A 1 and A 2 , and *2 is bonded to the other of A 1 and A 2 .
- a is an integer from 1 to 4.
- b is an integer from 0 to 3.
- L is an arylene group having 6 to 60 carbon atoms.
- G is selected from the group consisting of: a heteroaryl group having 3 to 60 ring carbon atoms, an alkyl group having 1 to 40 carbon atoms and substituted with at least one functional group, an alkenyl group having 2 to 40 carbon atoms and substituted with at least one functional group, an alkynyl group having 2 to 40 carbon atoms and substituted with at least one functional group, a cycloalkyl group having 3 to 60 ring carbon atoms and substituted with at least one functional group, a heterocycloalkyl group having 3 to 60 ring carbon atoms and substituted with at least one functional group, an alkoxy group having 1 to 40 carbon atoms and substituted with at least one functional group, an aryl group having 6 to 60 ring carbon atoms and substituted with at least one functional group, an aryloxy group having 6 to 60 ring carbon atoms and substituted with at least one functional group, an alkylsilyl group having 1 to 40 carbon atoms and substituted
- c is an integer from 0 to 4.
- Y is selected from the group consisting of: a deuterium atom, an unsubstituted aryl group having 6 to 60 ring carbon atoms, an unsubstituted alkyl group having 1 to 12 carbon atoms, an unsubstituted alkenyl group having 2 to 12 carbon atoms, and an unsubstituted alkynyl group having 2 to 12 carbon atoms.
- Z 1 and Z 2 are each independently selected from the group consisting of: an alkyl group having 1 to 6 carbon atoms, and an aryl group having 6 to 12 ring carbon atoms, and Z 1 and Z 2 are the same or different.
- the compound attached with at least one specific group [(L) b -G] is suitable as an electron transport material for OLEDs of any color, and allows the OLEDs using the same to have extended lifespan.
- each group of [(L) b -G] may be the same or different.
- two groups of [(L) b -G] may be represented by [(L 1 ) b1 -G 1 ] and [(L 2 ) b2 -G 2 ].
- b1 and b2 are each independently an integer from 0 to 3, and b1 and b2 are the same or different;
- L 1 and L 2 are each independently selected from the group for L as stated above, and L 1 and L 2 are the same or different;
- G 1 and G 2 are each independently selected from the group for G as stated above, and G 1 and G 2 are the same or different.
- (Y)s are the same or different.
- a is the integer 1.
- the heteroaryl group having 3 to 60 ring carbon atoms represented by G in Formulae (I), (I-I-I) to (I-I-IV), and (I-II-I) to (I-II-IV) is selected from the group consisting of: a furyl group, a pyrrolyl group, a thiophenyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group; a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group; an indolyl group, an isoindolyl group
- the heteroaryl group having 3 to 60 ring carbon atoms is selected from the group consisting of: a furyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a tetrazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyridazinyl group, a pyrimidinyl group, a triazinyl group, an isoindolyl group, an isobenzofuranyl group, an isobenzothiophenyl group, an indolizinyl group, a quinolizinyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimi
- heteroaryl group having 3 to 60 ring carbon atoms represented by G in Formulae (I), (I-I-I) to (I-I-IV), and (I-II-I) to (I-II-IV) is selected from the group consisting of:
- R 1 to R 5 are each independently selected from the group consisting of: a deuterium atom, a halogen group, a cyano group, a nitro group, a trifluoromethyl group, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 30 ring carbon atoms, a heterocycloalkyl group having 3 to 30 ring carbon atoms, an aryl group having 6 to 30 ring carbon atoms, a heteroaryl group having 3 to 30 ring carbon atoms, an alkoxy group having 1 to 40 carbon atoms, an aryloxy group having 6 to 30 ring carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 30 ring carbon atoms, an alkylboron group having 1 to 30 carbon atoms,
- the group [(L) b -G] is selected from the group consisting of:
- the aryl group having 6 to 60 ring carbon atoms and substituted with at least one functional group represented by G in Formulae (I), (I-I-I) to (I-I-IV), and (I-II-I) to (I-II-IV) is selected from the group consisting of: a phenyl group substituted with the at least one functional group, a biphenylyl group substituted with the at least one functional group, a terphenyl group substituted with the at least one functional group, a naphthyl group substituted with the at least one functional group, a phenanthryl group substituted with the at least one functional group, an anthracenyl group substituted with the at least one functional group, a benzanthryl group substituted with the at least one functional group, a fluorenyl group substituted with the at least one functional group, a chrysenyl group substituted with the at least one functional group, a fluoranthenyl group substituted with the
- the aryl group having 6 to 60 ring carbon atoms and substituted with at least one functional group represented by G in Formulae (I), (I-I-I) to (I-I-IV), and (I-II-I) to (I-II-IV) is selected from the group consisting of: a phenyl group substituted with the at least one functional group and a biphenyl group substituted with the at least one functional group.
- the aryl group having 6 to 60 ring carbon atoms and substituted with the at least one functional group represented by G in Formulae (I), (I-I-I) to (I-I-IV), and (I-II-I) to (I-II-IV) is selected from the group consisting of:
- R 1 is selected from the group consisting of: a deuterium atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 30 ring carbon atoms, a heterocycloalkyl group having 3 to 30 ring carbon atoms, an aryl group having 6 to 30 ring carbon atoms, a heteroaryl group having 3 to 30 ring carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryloxy group having 6 to 30 ring carbon atoms, an alkylsilyl group having 1 to 12 carbon atoms, an arylsilyl group having 6 to 30 ring carbon atoms, an alkylboron group having 1 to 12 carbon atoms, and an arylboron group having 6 to 30 ring carbon atoms.
- Y in Formulae (I), (I-I-I) to (I-I-IV), and (I-II-I) to (I-II-IV) is selected from the group consisting of: a deuterium atom, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, an anthracenyl group, a benzanthryl group, a fluorenyl group, a chrysenyl group, a fluoranthenyl group, a deuterated phenyl group, a deuterated biphenyl group, a deuterated terphenyl group, a deuterated naphthyl group, a deuterated phenanthryl group, a deuterated anthracenyl group, a deuterated benzanthryl group, a deuterated fluorenyl group, a deuterated ch
- b in Formula (I) is 0. That is, each G is directly attached on the main skeletal structure.
- L is selected from the group consisting of:
- L is selected from the group consisting of:
- said “arylene group having 6 to 60 ring carbon atoms” denoted by L may be an unsubstituted arylene group having 6 to 60 ring carbon atoms or an arylene group having 6 to 60 ring carbon atoms substituted with at least one substituent.
- the substituent may be selected from the group consisting of: a deuterium atom, a halogen group, a cyano group, a nitro group, a trifluoromethyl group, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 30 ring carbon atoms, a heterocycloalkyl group having 3 to 30 ring carbon atoms, an alkoxy group having 1 to 40 carbon atoms, an aryloxy group having 6 to 30 ring carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 30 ring carbon atoms, an alkylboron group having 1 to 30 carbon atoms, an arylboron group having 6 to 30 ring carbon atoms, a phosphine group having 1 to 30 carbon atoms, and
- heteroaryl group denoted by G may be an unsubstituted heteroaryl group or a heteroaryl group substituted with at least one substituent.
- the substituent on the heteroaryl group may be similar to any one of R 1 to R 5 as stated above.
- said “unsubstituted aryl group having 6 to 60 carbon atoms” denoted by Y means an aryl ring structure without any substituents which replace one or more hydrogen atoms on the aryl ring structure.
- said “unsubstituted alkyl group having 1 to 12 carbon atoms”, said “unsubstituted alkenyl group having 2 to 12 carbon atoms”, or said “unsubstituted alkynyl group having 2 to 12 carbon atoms” denoted by Y means an hydrocarbon skeletal structure without any hetero atoms.
- said “alkyl group” denoted by Z 1 and Z 2 may be an unsubstituted alkyl group or an alkyl group substituted with at least one substituent.
- the substituent on the alkyl group, alkenyl group, or alkynyl group may be, for example, but not limited to a deuterium atom.
- said “aryl group” denoted by Z 1 and Z 2 may be an unsubstituted aryl group or an aryl group substituted with at least one substituent.
- the substituent on the aryl group may be, for example, but not limited to a deuterium atom.
- the compound may be selected from the group consisting of:
- the present invention also provides an organic electronic device, comprising a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode.
- the organic layer comprises the novel compound as described above.
- the organic electronic device is an organic light emitting device (OLED).
- OLED organic light emitting device
- the organic light emitting device may comprise:
- the organic layer may be the electron transport layer, i.e., the electron transport layer comprises an electron transport material which is the novel compound as stated above.
- the electron transport layer may be a single-layered configuration or a multi-layered configuration disposed between the emission layer and the electron injection layer.
- the electron transport layer is the multi-layered configuration, e.g., the electron transport layer comprises a first electron transport layer and a second electron transport layer
- the first electron transport material of the first electron transport layer may be made of a single novel compound
- the second electron transport material of the second electron transport layer may be made of another single novel compound or any single conventional compound.
- the first electron transport material of the first electron transport layer may be made of a novel compound in combination with another single novel compound or any single conventional compound, and so as the second electron transport material.
- Said first and/or second electron transport layer comprises the novel compound such as Compounds 1 to 264.
- the OLEDs using the novel compound as the electron transport material can have an extended the lifespan compared to commercial OLEDs using known electron transport materials of ETL, such as 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 3,3′[5′[3-(3-pyridinyl)phenyl][1,1′:3′,1′′-terphenyl]-3,3′′-diyl]bispyridine (TmPyPb), 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), tris(2,4,6-trimethyl-3-(pyridin-3-yl)phenyl)borane (3 TPYMB), 1,3-bis(3,5-dipyrid-3-yl-phenyl)benzene (BmPyPb), and 9,10-bis(3-(
- the OLED comprises a hole blocking layer (HBL) formed between the electron transport layer and the emission layer, to block holes overflow from the emission layer to the electron transport layer.
- HBL hole blocking layer
- the organic layer may be the hole blocking layer, i.e., the hole blocking layer comprises a hole blocking material which is the novel compound as stated above. More specifically, said hole blocking layer comprises the novel compound such as Compounds 1 to 264.
- the OLEDs using the novel compound as the hole blocking material can have an extended lifespan compared to commercial OLEDs using known hole blocking materials of HBL, such as 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) and 2,3,5,6-tetramethyl-phenyl-1,4-(bis-phthalimide) (TMPP).
- BCP 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline
- TMPP 2,3,5,6-tetramethyl-phenyl-1,4-(bis-phthalimide)
- the hole injection layer may be a two-layered structure, i.e., the OLED comprises a first hole injection layer and a second hole injection layer disposed between the first electrode and the hole transport layer.
- Said first and second hole injection layers may be made of, for example, but not limited to: polyaniline, polyethylenedioxythiophene, 4,4′,4′′-Tris[(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), or N 1 ,N 1 ′-(biphenyl-4,4′-diyl)bis(N 1 -(naphthalen-1-yl)-N 4 ,N 4 ′-diphenylbenzene-1,4-diamine).
- m-MTDATA 4,4′,4′′-Tris[(3-methylphenyl)phenylamino]triphenylamine
- m-MTDATA 4,4′,4′′-Tris[(3-methylphenyl)phenylamino]triphenylamine
- the hole transport layer may be a two-layered structure, i.e., the OLED comprises a first hole transport layer and a second hole transport layer disposed between the two-layered hole injection layer and the emission layer.
- Said first and second hole transport layers may be made of, for example, but not limited to: 1,1-bis[(di-4-tolylamino)phenylcyclohexane](TAPC), a carbazole derivative such as N-phenyl carbazole, and N 4 ,N 4 ′-di(naphthalen-1-yl)-N 4 ,N 4′ -diphenylbiphenyl-4,4′-diamine (NPB).
- TAPC 1,1-bis[(di-4-tolylamino)phenylcyclohexane]
- NPB N-diphenylbiphenyl-4,4′-diamine
- the emission layer can be made of an emission material including a host and a dopant.
- the host of the emission material is, for example, but not limited to, 9-(4-(naphthalen-1-yl)phenyl)-10-(naphthalen-2-yl) anthracene.
- the dopant of the emission material is, for example, but not limited to: organometallic compounds of iridium (II) having quinoline derivative ligands or isoquinoline derivative ligands; an osmium complex; or a platinum complex.
- the dopant of the emission material is, for example, but not limited to: diaminofluorenes; diaminoanthracenes; or organometallic compounds of iridium (II) having phenylpyridine ligands.
- the dopant of the emission material is, for example, but not limited to: an aminoperylene derivative; a diaminochrysene; diaminopyrenes; or organicmetallic compounds of iridium (II) having pyridinato picolinate ligands.
- the OLED can emit lights in red, green or blue.
- the OLED comprises an electron blocking layer formed between the hole transport layer and the emission layer, to block electrons overflow from the emission layer to the hole transport layer.
- Said electron blocking layer may be made of 9,9′-[1,1′-biphenyl]-4,4′-diylbis-9H-carbazole (CBP) or 4,4′,4′′-tri(N-carbazolyl)-triphenylamine (TCTA), but it is not limited thereto.
- the OLED In the presence of such a hole blocking layer and/or an electron blocking layer in an OLED, the OLED has a higher luminous efficiency compared to a typical OLED.
- Said electron injection layer may be made of an electron injection material, for example, but not limited to (8-oxidonaphthalen-1-yl)lithium(II).
- Said first electrode is, for example, but not limited to, an indium-doped tin oxide electrode.
- Said second electrode has a work function lower than that of the first electrode.
- the second electrode is, for example, but not limited to, an aluminum electrode, an indium electrode, or a magnesium electrode.
- FIG. 1 illustrates a schematic cross-sectional view of an OLED
- FIGS. 2 to 19 respectively are 1 H nuclear magnetic resonance (NMR) spectra of compounds 1 to 18.
- the white solid product was identified as Intermediate A1-2 by a field desorption mass spectroscopy (FD-MS) analysis.
- the chemical structure was listed in Table 1.
- B′ is B(OH) 2 group
- 9,9-Dimethylfluorene-3-borortic acid pinacol ester (CAS No. 1346007-02-0) as Reactant R2 (1.2eq), Reactant B1 (1.0eq), Pd(OAc) 2 (0.015eq), PP11 3 (0.06eq), and K 2 CO 3 (3.0M, 1.5eq) were mixed in 200 ml of toluene, and the reaction mixture was heated to about 80° C. and stirred.
- Step 2 Intermediate A4-2 was synthesized in a similar manner as Intermediate A1-2 through step 2, except that the starting material Intermediate A1-1 was replaced by intermediate A4-1. The yield of step 2 was 70%. The chemical structure was listed in Table 2.
- Step 3 was synthesized in a similar manner that Intermediate A1-3 was obtained through foresaid step 3, except that the starting material Intermediate A1-2 was replaced by Intermediate A4-2. The yield of step 3 was 83%.
- Intermediate A4 was synthesized in a similar manner as Intermediate A1 through step 4, except that the starting material Intermediate A1-3 was replaced by Intermediate A4-3. The yield of step 4 was 63%.
- Intermediate A4 was identified by a FD-MS analysis. FD-MS analysis: C 23 H 17 Cl: theoretical value 328.83 and observed value 328.83. The chemical structure was listed in Table 2.
- Reactants Dn used for preparing a novel compound were listed in Table 4.
- Reactants D1, D3 to D23 were purchased from Sigma-Aldrich.
- a glass substrate coated with ITO layer (abbreviated in ITO substrate) in a thickness of 1500 ⁇ was placed in distilled water containing a detergent dissolved therein, and was ultrasonically washed.
- the detergent was a product manufactured by Fischer Co., and the distilled water was distilled water filtered twice through a filter (Millipore Co.). After the ITO layer had been washed for 30 minutes, it was ultrasonically washed twice with distilled water for 10 minutes. After the completion of washing, the glass substrate was ultrasonically washed with isopropyl alcohol, acetone and methanol solvents and then dried, after which it was transported to a plasma cleaner. Then the substrate was cleaned with oxygen plasma for 5 minutes, and then transferred to a vacuum evaporator.
- the ITO substrate was deposited with a first hole injection layer (HIL-1), a second hole injection layer (HIL-2), a first hole transporting layer (HTL-1), a second hole transporting layer (HTL-2), a blue/green/red emission layer (BEL/GEL/REL), an electron transporting layer (ETL), an electron injection layer (EIL), and a cathode (Cthd).
- HIL-1 hole injection layer
- HIL-2 first hole transporting layer
- HTL-2 first hole transporting layer
- HTL-2 blue/green/red emission layer
- ETL electron transporting layer
- EIL electron injection layer
- Cthd cathode
- HAT was a material for forming HIL-1 and HIL-2
- HI-2 was a material for forming HIL-2
- HT-1 and HT-2 were respectively materials for forming HTL-1 and HTL-2
- novel compounds of the present invention and commercial ET (BCP) were materials for forming ETL
- Liq was a material for forming ETL and EIL.
- RH/GH/BH were each a host material for forming REL/GEL/BEL
- RD/GD/BD were each a dopant for forming REL/GEL/BEL.
- red OLED device To prepare the red OLED device, multiple organic layers were respectively deposited on the ITO substrate according to the sequence as listed in Table 9, and the materials and the thicknesses of the organic layers in red OLED devices were also listed in Table 9.
- red, green, and blue OLED devices were measured by PR650 as photometer and Keithley 2400 as power supply. Color coordinates (x,y) were determined according to the CIE chromaticity scale (Commission Internationale de L'Eclairage, 1931). The results were shown in Tables 10 to 12. For the blue and red OLED devices, the data of Color coordinates (x,y) were collected at 1000 nits. For the green OLED devices, the data of Color coordinates (x,y) were collected at 3000 nits. For blue OLEDs, the evaluation of lifespan (T85) was defined as a period taken for luminance reduction to 85% of the initial luminance at 2000 nits. The results of blue OLEDs were shown in Table 10.
- lifespan (T95) was defined as a period taken for luminance reduction to 95% of the initial luminance at 7000 nits.
- the results of green OLEDs were shown in Table 11.
- lifespan (T90) was defined as a period taken for luminance reduction to 90% of the initial luminance at 6000 nits.
- the results of red OLEDs were shown in Table 12.
- the lifespans of blue OLEDs of E1 to E18 are all longer than those of C1 to C3, especially for C3. It demonstrated that adopting the novel compounds of the present invention as the electron transport material can effectively prolong the lifespan of the blue OLED.
- the lifespans of green OLEDs of E19 to E27 are all longer than those of C4 to C7, especially for C6 and C7. It demonstrated that adopting the novel compounds of the present invention as the electron transport material also can effectively prolong the lifespan of the green OLED.
- the lifespans of red OLEDs of E28 to E34 are all longer than those of C8 to C11, especially for C10 and C11. It demonstrated that adopting the novel compounds of the present invention as the electron transport material also can effectively prolong the lifespan of the red OLED, like the blue and green OLEDs.
- the novel compounds of the present invention can be act as the suitable electron transport material and has the effect of prolonging the lifespan of the red, green, and blue OLEDs.
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Abstract
Provided are a novel compound and an organic electronic device using the same. The novel compound is represented by the following Formula (I):
-
- wherein A1 and A2 each represent a carbon atom; *1 is bonded to one of A1 and A2, and *2 is bonded to the other of A1 and A2; a is an integer from 1 to 4; b is an integer from 0 to 3.
Description
- Pursuant to 35 U.S.C. § 119(e), this application claims the benefit of the priority to U.S. Provisional Patent Application No. 62/680,625, filed Jun. 5, 2018. The content of the prior application is incorporated herein by its entirety.
- The present invention relates to a novel compound and an organic electronic device using the same, more particularly to a novel compound as an electron transport material for an electron transport layer and an organic electronic device using the same.
- With the advance of technology, various organic electronic devices that make use of organic materials have been energetically developed. Examples of organic electronic devices include organic light emitting devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors.
- OLED was initially invented and proposed by Eastman Kodak Company through a vacuum evaporation method. Dr. Ching M. Tang and Steven Van Slyke of Kodak Company deposited an electron transport material such as tris(8-hydroxyquinoline)aluminum(III) (abbreviated as Alq3) on a transparent indium tin oxide glass (abbreviated as ITO glass) formed with a hole transport layer of organic aromatic diamine thereon, and subsequently deposited a metal electrode onto an electron transport layer to complete the fabrication of the OLED. OLEDs have attracted lots of attention due to their numerous advantages, such as fast response speed, light weight, compactness, wide viewing angle, high brightness, higher contrast ratio, no need of backlight, and low power consumption. However, the OLEDs still have the problems such as short lifespan.
- One of the approaches in prior art is to interpose some interlayers between the cathode and the anode. With reference to
FIG. 1 , a modifiedOLED 1 may have a structure of asubstrate 11, ananode 12, a hole injection layer 13 (abbreviated as HIL), a hole transport layer 14 (abbreviated as HTL), an emission layer 15 (abbreviated as EL), an electron transport layer 16 (abbreviated as ETL), an electron injection layer 17 (abbreviated as EIL), and acathode 18 stacked in sequence. When a voltage is applied between theanode 12 and thecathode 18, the holes injected from theanode 12 move to the EL via HIL and HTL and the electrons injected from thecathode 18 move to the EL via EIL and ETL. Recombination of the electrons and the holes occurs in the EL to generate excitons, thereby emitting a light when the excitons decay from excited state to ground state. - Another approach is to modify the materials of ETL for OLEDs to render the electron transport materials to exhibit hole-blocking ability. Examples of conventional electron transport materials include 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 3,3′-[5′-[3-(3-pyridinyl)phenyl][1,1′: 3′,1″-terphenyl]-3,3″-diyl]bispyridine (TmPyPb), 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), tris(2,4,6-trimethyl-3-(pyridin-3-yl)phenyl)borane (3TPYMB), 1,3-bis(3,5-dipyrid-3-yl-phenyl)benzene (BmPyPb), and 9,10-bis(3-(pyridin-3-yl)phenyl)anthracene (DPyPA).
- However, even using the foresaid electron transport materials, the lifespan of OLEDs still needs to be improved. Therefore, the present invention provides a novel compound to mitigate or obviate the problems in the prior art.
- An objective of the present invention is to provide a novel compound useful for an organic electronic device.
- Another objective of the present invention is to provide an organic electronic device using the novel compound, so as to prolong the lifespan of the organic electronic device.
- To achieve the foresaid objectives, the present invention provides a novel compound represented by the following Formula (I):
- In Formula (I), A1 and A2 each represent a carbon atom; *1 is bonded to one of A1 and A2, and *2 is bonded to the other of A1 and A2.
- In Formula (I), a is an integer from 1 to 4.
- In Formula (I), b is an integer from 0 to 3.
- In Formula (I), L is an arylene group having 6 to 60 carbon atoms.
- In Formula (I), G is selected from the group consisting of: a heteroaryl group having 3 to 60 ring carbon atoms, an alkyl group having 1 to 40 carbon atoms and substituted with at least one functional group, an alkenyl group having 2 to 40 carbon atoms and substituted with at least one functional group, an alkynyl group having 2 to 40 carbon atoms and substituted with at least one functional group, a cycloalkyl group having 3 to 60 ring carbon atoms and substituted with at least one functional group, a heterocycloalkyl group having 3 to 60 ring carbon atoms and substituted with at least one functional group, an alkoxy group having 1 to 40 carbon atoms and substituted with at least one functional group, an aryl group having 6 to 60 ring carbon atoms and substituted with at least one functional group, an aryloxy group having 6 to 60 ring carbon atoms and substituted with at least one functional group, an alkylsilyl group having 1 to 40 carbon atoms and substituted with at least one functional group, an arylsilyl group having 6 to 60 ring carbon atoms and substituted with at least one functional group, an alkylboron group having 1 to 40 carbon atoms and substituted with at least one functional group, an arylboron group having 6 to 60 ring carbon atoms and substituted with at least one functional group, a phosphine group having 1 to 40 carbon atoms and substituted with at least one functional group, and a phosphine oxide group having 1 to 40 carbon atoms and substituted with at least one functional group, any isomeric groups thereof, and any deuterated analogs thereof, wherein the functional group is selected from the group consisting of: a cyano group, a nitro group, a trifluoromethyl group, a fluoro group, and a chloro group.
- In Formula (I), c is an integer from 0 to 4.
- In Formula (I), Y is selected from the group consisting of: a deuterium atom, an unsubstituted aryl group having 6 to 60 ring carbon atoms, an unsubstituted alkyl group having 1 to 12 carbon atoms, an unsubstituted alkenyl group having 2 to 12 carbon atoms, and an unsubstituted alkynyl group having 2 to 12 carbon atoms.
- In Formula (I), Z1 and Z2 are each independently selected from the group consisting of: an alkyl group having 1 to 6 carbon atoms, and an aryl group having 6 to 12 ring carbon atoms, and Z1 and Z2 are the same or different.
- The compound attached with at least one specific group [(L)b-G] is suitable as an electron transport material for OLEDs of any color, and allows the OLEDs using the same to have extended lifespan.
- When a in Formula (I) is an integer from 2 to 4, each group of [(L)b-G] may be the same or different. For example, when a is the
integer 2, two groups of [(L)b-G] may be represented by [(L1)b1-G1] and [(L2)b2-G2]. Herein, b1 and b2 are each independently an integer from 0 to 3, and b1 and b2 are the same or different; L1 and L2 are each independently selected from the group for L as stated above, and L1 and L2 are the same or different; G1 and G2 are each independently selected from the group for G as stated above, and G1 and G2 are the same or different. - Likely, when c is an integer from 2 to 4, (Y)s are the same or different. Preferably, only one group of [(L)b-G] is attached on the main skeletal structure. That is, in one embodiment, a is the
integer 1. - In the case that *1 is bonded to A1 and *2 is bonded to A2, the compound may be represented by
- More specifically, the compound represented by Formula (I-I) is represented by any one of the following formulae:
- In the case that *1 is bonded to A2 and *2 is bonded to A1, the compound may be represented by
- More specifically, the compound represented by Formula (I-II) is represented by any one of the following formulae:
- Preferably, the heteroaryl group having 3 to 60 ring carbon atoms represented by G in Formulae (I), (I-I-I) to (I-I-IV), and (I-II-I) to (I-II-IV) is selected from the group consisting of: a furyl group, a pyrrolyl group, a thiophenyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group; a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group; an indolyl group, an isoindolyl group, a benzofuranyl group, an isobenzofuranyl group, a benzothiophenyl group, an isobenzothiophenyl group, an indolizinyl group, a quinolizinyl group, a quinolyl group, an isoquinolyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, an indazolyl group, a benzisoxazolyl group, a benzisothiazolyl group; a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a biscarbazolyl group, a coumarinyl group, a chromenyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a phenothiazinyl group, a phenoxazinyl group, an azatriphenylenyl group, a diazatriphenylenyl group, a xanthenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, a benzofuranobenzothiophenyl group, a benzothienobenzothiophenyl group, a dibenzofuranonaphthyl group, a dibenzothienonaphthyl group, a dinaphthothienothiophenyl group, a dinaphtho carbazolyl group, a dibenzo[b,f]azepin group, a tribenzo[b,d,f]azepin group, a dibenzo[b,f]oxepin group, a tribenzo[b,d,f]oxepin group, any isomeric groups thereof, and any deuterated analogs thereof.
- More specifically, the heteroaryl group having 3 to 60 ring carbon atoms, represented by G in Formula (I) and especially in Formula (I-I-I), is selected from the group consisting of: a furyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a tetrazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyridazinyl group, a pyrimidinyl group, a triazinyl group, an isoindolyl group, an isobenzofuranyl group, an isobenzothiophenyl group, an indolizinyl group, a quinolizinyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, an indazolyl group, a benzisoxazolyl group, a benzisothiazolyl group, a biscarbazolyl group, a coumarinyl group, a chromenyl group, a phenanthridinyl group, an azatriphenylenyl group, a diazatriphenylenyl group, a xanthenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, a benzofuranobenzothiophenyl group, a benzothienobenzothiophenyl group, a dibenzofuranonaphthyl group, a dibenzothienonaphthyl group, a dinaphthothienothiophenyl group, a dinaphtho carbazolyl group, a dibenzo[b,f]azepin group, a tribenzo[b,d,f]azepin group, a dibenzo[b,f]oxepin group, a tribenzo[b,d,f]oxepin group, any isomeric groups thereof, and any deuterated analogs thereof.
- Specifically, the heteroaryl group having 3 to 60 ring carbon atoms represented by G in Formulae (I), (I-I-I) to (I-I-IV), and (I-II-I) to (I-II-IV) is selected from the group consisting of:
- wherein o is an integer from 0 to 2; m is an integer from 0 to 3; n is an integer from 0 to 4; p is an integer from 0 to 5;
- wherein R1 to R5 are each independently selected from the group consisting of: a deuterium atom, a halogen group, a cyano group, a nitro group, a trifluoromethyl group, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 30 ring carbon atoms, a heterocycloalkyl group having 3 to 30 ring carbon atoms, an aryl group having 6 to 30 ring carbon atoms, a heteroaryl group having 3 to 30 ring carbon atoms, an alkoxy group having 1 to 40 carbon atoms, an aryloxy group having 6 to 30 ring carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 30 ring carbon atoms, an alkylboron group having 1 to 30 carbon atoms, an arylboron group having 6 to 30 ring carbon atoms, a phosphine group having 1 to 30 carbon atoms, and a phosphine oxide group having 1 to 30 carbon atoms.
- Preferably, the group [(L)b-G] is selected from the group consisting of:
- Preferably, the aryl group having 6 to 60 ring carbon atoms and substituted with at least one functional group represented by G in Formulae (I), (I-I-I) to (I-I-IV), and (I-II-I) to (I-II-IV) is selected from the group consisting of: a phenyl group substituted with the at least one functional group, a biphenylyl group substituted with the at least one functional group, a terphenyl group substituted with the at least one functional group, a naphthyl group substituted with the at least one functional group, a phenanthryl group substituted with the at least one functional group, an anthracenyl group substituted with the at least one functional group, a benzanthryl group substituted with the at least one functional group, a fluorenyl group substituted with the at least one functional group, a chrysenyl group substituted with the at least one functional group, a fluoranthenyl group substituted with the at least one functional group, and any deuterated analogs thereof.
- More preferably, the aryl group having 6 to 60 ring carbon atoms and substituted with at least one functional group represented by G in Formulae (I), (I-I-I) to (I-I-IV), and (I-II-I) to (I-II-IV) is selected from the group consisting of: a phenyl group substituted with the at least one functional group and a biphenyl group substituted with the at least one functional group.
- Specifically, the aryl group having 6 to 60 ring carbon atoms and substituted with the at least one functional group represented by G in Formulae (I), (I-I-I) to (I-I-IV), and (I-II-I) to (I-II-IV) is selected from the group consisting of:
- wherein r is an integer from 1 to 5; s is an integer from 0 to 4; the total of r and s is not more than 5;
- wherein R1 is selected from the group consisting of: a deuterium atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 30 ring carbon atoms, a heterocycloalkyl group having 3 to 30 ring carbon atoms, an aryl group having 6 to 30 ring carbon atoms, a heteroaryl group having 3 to 30 ring carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryloxy group having 6 to 30 ring carbon atoms, an alkylsilyl group having 1 to 12 carbon atoms, an arylsilyl group having 6 to 30 ring carbon atoms, an alkylboron group having 1 to 12 carbon atoms, and an arylboron group having 6 to 30 ring carbon atoms.
- Preferably, Y in Formulae (I), (I-I-I) to (I-I-IV), and (I-II-I) to (I-II-IV) is selected from the group consisting of: a deuterium atom, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, an anthracenyl group, a benzanthryl group, a fluorenyl group, a chrysenyl group, a fluoranthenyl group, a deuterated phenyl group, a deuterated biphenyl group, a deuterated terphenyl group, a deuterated naphthyl group, a deuterated phenanthryl group, a deuterated anthracenyl group, a deuterated benzanthryl group, a deuterated fluorenyl group, a deuterated chrysenyl group, and a deuterated fluoranthenyl group.
- Preferably, b in Formula (I) is 0. That is, each G is directly attached on the main skeletal structure.
- In the case that b in Formulae (I), (I-I-I) to (I-I-IV), and (I-II-I) to (I-II-IV) is an integer from 1 to 3, L is selected from the group consisting of:
- Preferably, L is selected from the group consisting of:
- More specifically, L is
- In this specification, said “arylene group having 6 to 60 ring carbon atoms” denoted by L may be an unsubstituted arylene group having 6 to 60 ring carbon atoms or an arylene group having 6 to 60 ring carbon atoms substituted with at least one substituent. The substituent may be selected from the group consisting of: a deuterium atom, a halogen group, a cyano group, a nitro group, a trifluoromethyl group, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 30 ring carbon atoms, a heterocycloalkyl group having 3 to 30 ring carbon atoms, an alkoxy group having 1 to 40 carbon atoms, an aryloxy group having 6 to 30 ring carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 30 ring carbon atoms, an alkylboron group having 1 to 30 carbon atoms, an arylboron group having 6 to 30 ring carbon atoms, a phosphine group having 1 to 30 carbon atoms, and a phosphine oxide group having 1 to 30 carbon atoms.
- In this specification, said “heteroaryl group” denoted by G may be an unsubstituted heteroaryl group or a heteroaryl group substituted with at least one substituent. The substituent on the heteroaryl group may be similar to any one of R1 to R5 as stated above.
- In this specification, said “unsubstituted aryl group having 6 to 60 carbon atoms” denoted by Y means an aryl ring structure without any substituents which replace one or more hydrogen atoms on the aryl ring structure. Likely, said “unsubstituted alkyl group having 1 to 12 carbon atoms”, said “unsubstituted alkenyl group having 2 to 12 carbon atoms”, or said “unsubstituted alkynyl group having 2 to 12 carbon atoms” denoted by Y means an hydrocarbon skeletal structure without any hetero atoms.
- In this specification, said “alkyl group” denoted by Z1 and Z2 may be an unsubstituted alkyl group or an alkyl group substituted with at least one substituent. The substituent on the alkyl group, alkenyl group, or alkynyl group may be, for example, but not limited to a deuterium atom.
- In this specification, said “aryl group” denoted by Z1 and Z2 may be an unsubstituted aryl group or an aryl group substituted with at least one substituent. The substituent on the aryl group may be, for example, but not limited to a deuterium atom.
- For example, the compound may be selected from the group consisting of:
- The present invention also provides an organic electronic device, comprising a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode. The organic layer comprises the novel compound as described above.
- Preferably, the organic electronic device is an organic light emitting device (OLED).
- Specifically, the organic light emitting device may comprise:
- a hole injection layer formed on the first electrode;
- a hole transport layer formed on the hole injection layer;
- an emission layer formed on the hole transport layer;
- an electron transport layer formed on the emission layer;
- an electron injection layer formed between the electron transport layer and the second electrode.
- In one embodiment, the organic layer may be the electron transport layer, i.e., the electron transport layer comprises an electron transport material which is the novel compound as stated above.
- For example, the electron transport layer may be a single-layered configuration or a multi-layered configuration disposed between the emission layer and the electron injection layer. When the electron transport layer is the multi-layered configuration, e.g., the electron transport layer comprises a first electron transport layer and a second electron transport layer, the first electron transport material of the first electron transport layer may be made of a single novel compound and the second electron transport material of the second electron transport layer may be made of another single novel compound or any single conventional compound. Or, the first electron transport material of the first electron transport layer may be made of a novel compound in combination with another single novel compound or any single conventional compound, and so as the second electron transport material.
- Said first and/or second electron transport layer comprises the novel compound such as
Compounds 1 to 264. The OLEDs using the novel compound as the electron transport material can have an extended the lifespan compared to commercial OLEDs using known electron transport materials of ETL, such as 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 3,3′[5′[3-(3-pyridinyl)phenyl][1,1′:3′,1″-terphenyl]-3,3″-diyl]bispyridine (TmPyPb), 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), tris(2,4,6-trimethyl-3-(pyridin-3-yl)phenyl)borane (3 TPYMB), 1,3-bis(3,5-dipyrid-3-yl-phenyl)benzene (BmPyPb), and 9,10-bis(3-(pyridin-3-yl)phenyl)anthracene (DPyPA). - Preferably, the OLED comprises a hole blocking layer (HBL) formed between the electron transport layer and the emission layer, to block holes overflow from the emission layer to the electron transport layer.
- In another embodiment, the organic layer may be the hole blocking layer, i.e., the hole blocking layer comprises a hole blocking material which is the novel compound as stated above. More specifically, said hole blocking layer comprises the novel compound such as
Compounds 1 to 264. The OLEDs using the novel compound as the hole blocking material can have an extended lifespan compared to commercial OLEDs using known hole blocking materials of HBL, such as 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) and 2,3,5,6-tetramethyl-phenyl-1,4-(bis-phthalimide) (TMPP). - Preferably, the hole injection layer may be a two-layered structure, i.e., the OLED comprises a first hole injection layer and a second hole injection layer disposed between the first electrode and the hole transport layer.
- Said first and second hole injection layers may be made of, for example, but not limited to: polyaniline, polyethylenedioxythiophene, 4,4′,4″-Tris[(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), or N1,N1′-(biphenyl-4,4′-diyl)bis(N1-(naphthalen-1-yl)-N4,N4′-diphenylbenzene-1,4-diamine).
- Preferably, the hole transport layer may be a two-layered structure, i.e., the OLED comprises a first hole transport layer and a second hole transport layer disposed between the two-layered hole injection layer and the emission layer.
- Said first and second hole transport layers may be made of, for example, but not limited to: 1,1-bis[(di-4-tolylamino)phenylcyclohexane](TAPC), a carbazole derivative such as N-phenyl carbazole, and N4,N4′-di(naphthalen-1-yl)-N4,N4′-diphenylbiphenyl-4,4′-diamine (NPB).
- Preferably, the emission layer can be made of an emission material including a host and a dopant. The host of the emission material is, for example, but not limited to, 9-(4-(naphthalen-1-yl)phenyl)-10-(naphthalen-2-yl) anthracene.
- For red OLEDs, the dopant of the emission material is, for example, but not limited to: organometallic compounds of iridium (II) having quinoline derivative ligands or isoquinoline derivative ligands; an osmium complex; or a platinum complex. For green OLEDs, the dopant of the emission material is, for example, but not limited to: diaminofluorenes; diaminoanthracenes; or organometallic compounds of iridium (II) having phenylpyridine ligands. For blue OLEDs, the dopant of the emission material is, for example, but not limited to: an aminoperylene derivative; a diaminochrysene; diaminopyrenes; or organicmetallic compounds of iridium (II) having pyridinato picolinate ligands. With various host materials of the emission layer, the OLED can emit lights in red, green or blue.
- Preferably, the OLED comprises an electron blocking layer formed between the hole transport layer and the emission layer, to block electrons overflow from the emission layer to the hole transport layer. Said electron blocking layer may be made of 9,9′-[1,1′-biphenyl]-4,4′-diylbis-9H-carbazole (CBP) or 4,4′,4″-tri(N-carbazolyl)-triphenylamine (TCTA), but it is not limited thereto.
- In the presence of such a hole blocking layer and/or an electron blocking layer in an OLED, the OLED has a higher luminous efficiency compared to a typical OLED.
- Said electron injection layer may be made of an electron injection material, for example, but not limited to (8-oxidonaphthalen-1-yl)lithium(II).
- Said first electrode is, for example, but not limited to, an indium-doped tin oxide electrode.
- Said second electrode has a work function lower than that of the first electrode. The second electrode is, for example, but not limited to, an aluminum electrode, an indium electrode, or a magnesium electrode.
- Other objectives, advantages and novel features of the invention will become more apparent from the following detailed description when taken in conjunction with the accompanying drawings.
-
FIG. 1 illustrates a schematic cross-sectional view of an OLED; -
FIGS. 2 to 19 respectively are 1H nuclear magnetic resonance (NMR) spectra ofcompounds 1 to 18. - Hereinafter, one skilled in the arts can easily realize the advantages and effects of a novel compound and an organic light emitting device using the same in accordance with the present invention from the following examples. It should be understood that the descriptions proposed herein are just preferable examples only for the purpose of illustrations, not intended to limit the scope of the invention. Various modifications and variations could be made in order to practice or apply the present invention without departing from the spirit and scope of the invention.
- Intermediate An used for preparing a novel compound was synthesized by the following steps. The synthesis pathway of Intermediate An was summarized in Scheme A1.
- Where in B′ is B(OH)2 group or
- group.
- Taking Intermediate A1 as an example of Intermediate An which is synthesized by Scheme A1, the synthesis pathway of Intermediate A1 was summarized in Scheme A1-1.
- 9,9-Dimethylfluorene-2-boronic acid (CAS No. 333432-28-3) as Reactant R.1 (1.2eq), Reactant 131 (1.0eq), palladium(11) acetate [Pd(OAc)2] (0.015eq), triphenylphosphine (PPh3) (0.06eq), and potassium carbonate (K2CO3) (3.0M, 1.5eq) were mixed in 200 ml of toluene, and the reaction mixture was heated to about 80° C. and stirred. After completion of the reaction, the reaction mixture was cooled to room temperature, and the crude product was extracted with saturated aqueous solution of sodium chloride and ethyl acetate (EA) and collected by the organic layer. The organic layer was dried over magnesium sulfate (MgSO4), separated by filtration with silica gel and concentrated under reduced pressure. A resulting residue was suspended in hexane, and the suspension was then filtered again and washed with hexane to obtain Intermediate A1-1. Intermediate A1-1 could be directly used in
step 2 without further purification. - Intermediate A1-1 (1.0eq) and tetra-n-butylammonium fluoride (TBAF) (1.5eq) were dissolved in tetrahydrofuran (THF) (0.3M) and stirred at room temperature for 1 hour. The solvent was then removed under reduced pressure, and the residue was purified with column chromatography to get a white solid product. The yield of
step 2 was 79%. - The white solid product was identified as Intermediate A1-2 by a field desorption mass spectroscopy (FD-MS) analysis. The chemical structure was listed in Table 1.
- Cesium hydroxide hydrate (CsOH*H2O)(0.3 eq) were dissolved in N-methyl-2-pyrrolidone (NMP)(0.3M) and stirred at room temperature for 10 minutes. The solution was then added Maki (1.7 eq) and intermediate A1-2, and the mixture were stirred and heated at 110° C. for 6 hrs. The solvent was then removed under reduced pressure, and the residue was purified with column chromatography by using Toluene/Hexane (2/1) to get oil type product. The yield of
step 3 was 85%. - Intermediate A1-3 (1 eq) was dissolved in dichloromethane (CH2Cl2)(0.3 M) and cooled to 0° C. Then the solution was added CF3SO3H (0.2 eq) slowly drop by drop and stirred for 2 hrs at 0° C. After completion of the reaction, the solvent was quenched by NaHCO3(aq), then removed the water layer. The solvent contained in the organic layer was removed under reduced pressure, and the residue was purified with column chromatography to obtain a white solid product. The yield of
step 4 was 85%. - The white solid product was identified as Intermediate A1 by a FD-MS analysis. FD-MS analysis: C23H17Cl: theoretical value 328.83 and observed value 328.83. The chemical structure was listed in Table 1.
- Syntheses of Intermediates A2 and A3
- Intermediates A2 and A3, which also can be used for preparing a novel compound, were respectively synthesized in a similar manner as Intermediate A1 through
steps 1 to 4, except that the starting material Reactant B1 was replaced with Reactants B2 and B3, respectively. All intermediates were analyzed as described above, and the results were listed in Table 1. -
TABLE 1 Reactants An and Bn used for preparing Intermediates An, chemical structures of Intermediates An-1, An-2, An-3, and An, yields of Intermediates An-2, An-3, and An, formulae, and mass analyzed by FD-MS of Intermediates A1 to A3 Reactant An No. Reactant A1 Chemical Structure/ CAS No. of Reactant Bn Reac- tant B1 Reac- tant B2 Chemical Structure of Intermediate An-1 Inter- mediate A1-1 Inter- mediate A2-1 Chemical Structure of Intermediate An-2 Inter- mediate A1-2 Inter- mediate A2-2 Yield(%) 79 81 Chemical Structure of Intermediate An-3 Inter- mediate A1-3 Inter- mediate A2-3 Yield(%) 85 82 Chemical Structure of Intermediate An Inter- mediate A1 Inter- mediate A2 Yield(%) 85 83 Formula/ C23H17Cl/ C23H17Cl/ Mass (M+) 328.83 328.83 Reactant An No. Reactant A1 Chemical Structure/ CAS No. of Reactant Bn Reac- tant B3 Chemical Structure of Intermediate An-1 Inter- mediate A3-1 Chemical Structure of Intermediate An-2 Inter- mediate A3-2 Yield(%) 66 Chemical Structure of Intermediate An-3 Inter- mediate A3-3 Yield(%) 73 Chemical Structure of Intermediate An Inter- mediate A3 Yield(%) 82 Formula/ C23H17Cl/ Mass (M+) 328.83 - In addition to Intermediates A1 to A3, one person skilled in the art can adopt other applicable starting materials and successfully synthesize other desired intermediates through a reaction mechanism similar to Scheme A1-1.
- Intermediate An used for preparing a novel compound can also be synthesized by the following steps. The synthesis pathway of Intermediate An was summarized in Scheme A2.
- Wherein B′ is B(OH)2 group or
- group.
- Taking Intermediate A4 as an example of Intermediate An which is synthesized by Scheme A2, the synthesis pathway of Intermediate A4 was summarized in Scheme A2-1.
- 9,9-Dimethylfluorene-3-borortic acid pinacol ester (CAS No. 1346007-02-0) as Reactant R2 (1.2eq), Reactant B1 (1.0eq), Pd(OAc)2 (0.015eq), PP113 (0.06eq), and K2CO3 (3.0M, 1.5eq) were mixed in 200 ml of toluene, and the reaction mixture was heated to about 80° C. and stirred. After completion of the reaction, the reaction mixture was cooled to room temperature, and the crude product was extracted with saturated aqueous solution of sodium chloride and ethyl acetate and collected by the organic layer The organic layer was dried over MgSO4, separated by filtration with silica gel and concentrated under reduced pressure. A resulting residue was suspended in hexane, the suspension was then filtered again and washed with hexane to obtain Intermediate A4-1. Intermediate A4-1 could be directly used in
step 2 without further purification. - Intermediate A4-2 was synthesized in a similar manner as Intermediate A1-2 through
step 2, except that the starting material Intermediate A1-1 was replaced by intermediate A4-1. The yield ofstep 2 was 70%. The chemical structure was listed in Table 2. - Intermediate A4-3 was synthesized in a similar manner that Intermediate A1-3 was obtained through
foresaid step 3, except that the starting material Intermediate A1-2 was replaced by Intermediate A4-2. The yield ofstep 3 was 83%. - Intermediate A4 was synthesized in a similar manner as Intermediate A1 through
step 4, except that the starting material Intermediate A1-3 was replaced by Intermediate A4-3. The yield ofstep 4 was 63%. Intermediate A4 was identified by a FD-MS analysis. FD-MS analysis: C23H17Cl: theoretical value 328.83 and observed value 328.83. The chemical structure was listed in Table 2. - Intermediate A5, which also can be used for preparing a novel compound, was respectively synthesized in a similar manner as Intermediate A4 through
steps 1 to 4, except that the starting material Reactant B1 was replaced with Reactants B2. All intermediates were analyzed as described above, and the results were listed in Table 2. -
TABLE 2 Reactants An and Bn used for preparing Intermediates An, chemical structures of Intermediates An-1, An-2 and An, yields of Intermediates An-2 and An, formulae, and mass analyzed by FD-MS of Intermediates A4 and A5 Reactant An No. Reactant An Chemical Structure/ CAS No. of Reactant Bn Reac- tant B1 Reac- tant B2 Chemical Structure of Intermediate An-1 Inter- mediate A4-1 Inter- mediate A5-1 Chemical Structure of Intermediate An-2 Inter- mediate A4-2 Inter- mediate A5-2 Yield(%) 75 84 Chemical Structure of Intermediate An-3 Inter- mediate A4-3 Inter- mediate A5-3 Yield(%) 83 78 Chemical Structure of Intermediate An-3 Inter- mediate A4 Inter- mediate A5 Yield(%) 63 67 Formula/ C23H17Cl/ C23H17Cl/ Mass (M+) 328.83 328.83 - Modifications of Intermediates A4 and A5
- In addition to Intermediates A4 and A5, one person skilled in the art can adopt other applicable starting materials and successfully synthesize other desired intermediates through a reaction mechanism similar to Scheme A2-1. Applicable modifications of Intermediate A4 and A5 may be, for example, but not limited to, Intermediate A6 as follows.
- The general synthesis pathway of Intermediate An-B was summarized in Scheme A3.
- Taking Intermediate A1-B as an example of Intermediate An-B, the synthesis pathway of Intermediate A1-B was summarized in Scheme A3-1.
- A mixture of Intermediate A1 (1.0 eq), bis(pinacolato)diboron (1.20 eq), tris(dibenzylideneacetone)dipalladium(0)[Pd2(dba)3)] (0.015 eqdicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine(0.03 eq, SPhos) and potassium acetate (KOAc) (1.5 eq) in
anhydrous 1,4-dioxane (0.5 M) was stirred at 110° C. for 8 hours under nitrogen atmosphere. After cooling to room temperature, the solvent was then removed under reduced pressure, and the residue was purified with column chromatography to obtain a pale yellow solid product. The yield ofstep 5 was 89%. - The pale yellow solid product was identified as Intermediate A1-B by a FD-MS analysis. The chemical structure, yield, formula, and mass analyzed by FD-MS of Intermediate A1-B were listed in Table 3.
- Intermediates A2-B to A5-B, which also can be used for preparing a novel compound, were respectively synthesized in a similar manner as Intermediate A1-B through
step 4, except that the starting material Intermediate A1 was replaced with Intermediate A2 to A5, respectively. All intermediates were analyzed as described above, and the results were listed in Table 3. -
TABLE 3 Intermediates An used for preparing Intermediates An-B, chemical structures of Intermediates An and An-B, yields of Intermediates An-B, formulae, and mass analyzed by FD-MS of Intermediates An-B Intermediate An-B For- mula/ Intermediate An Yield Mass Chemical Structure Chemical Structure (%) (M+) In- ter- me- di- ate A1 In- ter- me- di- ate A1- B 89 C29H29 BO2/ 420.35 In- ter- me- di- ate A2 In- ter- me- di- ate A2- B 95 C29H29 BO2/ 420.35 In- ter- me- di- ate A3 In- ter- me- di- ate A3- B 70 C29H29 BO2/ 420.35 In- ter- me- di- ate A4 In- ter- me- di- ate A4- B 96 C29H29 BO2/ 420.35 In- ter- me- di- ate A5 In- ter- me- di- ate A5- B 83 C29H29 BO2/ 420.35 - In addition to Intermediates A1-B to A5-B, one person skilled in the art can adopt other starting materials and successfully synthesize other desired intermediates through a reaction mechanism similar to Scheme A3-1.
- Applicable modifications of Intermediates A1-B to A5-B may be, for example, but is not limited to, Intermediate A6-B as follows.
- Reactants Dn used for preparing a novel compound were listed in Table 4. Reactants D1, D3 to D23 were purchased from Sigma-Aldrich.
-
TABLE 4 chemical structures and the CAS No. of the Reactants D1 to D23 Reactant D1 Reactant D2 Reactant D3 Reactant D4 Reactant D5 Reactant D6 Reactant D7 Reactant D8 Reactant D9 Reactant D10 Reactant D11 Reactant D12 Reactant D13 Reactant D14 Reactant D15 Reactant D16 Reactant D17 Reactant D18 Reactant D19 Reactant D20 Reactant D21 Reactant D22 Reactant D23 - The synthesis pathway of the Reactant D2 was summarized in Scheme D2.
- 4-bromobenzaldehyde (CAS No. 1122-91-4) (1.0 eq) and 1-[4-(3-Pyridinyl)phenyl]ethanone (CAS No. 90395-45-2) (1.0 eq) dissolved in absolute ethanol (0.5 M) were stirred, and an aqueous solution of potassium hydroxide (KOH) (3.0 eq, 2.5 M) was added dropwise at 0° C., and then the reaction mixture was stirred at room temperature for 12 hours. After that, 4-bromobenzamidine.HCl (CAS No. 1670-14-0) (1.0 eq) was added to the foresaid reaction mixture and heated at reflux temperature for another 6 hours. After completion of the reaction, the solvent was then removed under reduced pressure, and the residue was purified with column chromatography to get a white solid product in a yield of 34%. The white solid product was identified as Reactant D2 by a FD-MS analysis. FD-MS analysis: C27H18BrN3: theoretical value 464.36 and observed value 464.36. The chemical structure was listed in Table 4.
- Synthesis of Novel Compounds
- Each of the foresaid Intermediates, e.g., Intermediates An and An-B could be reacted with various Reactants Dn to synthesize various claimed novel compounds. The general synthesis pathway of the claimed novel compound was summarized in Scheme I. In the following Scheme I, “Intermediate A” may be any one of the foresaid Intermediates An and An-B as listed in Tables 1 to 3 or the like, and “Reactant Dn” may be any one of Reactants D1 to D23 as listed in Table 4. The compounds were each synthesized by the following method I or method II, and the results were listed in Table 5.
- Intermediate A (1.0eq), Reactant Dn (1.2eq), Pd(OAc)2 (0.01eq), and 2-(dicyclohexylphosphino)biphenyl [P(Cy)2(2-biPh)] (0.04eq) were stirred in a mixed solution of toluene/ethanol(0.5M, v/v=10/1), and 3.0M of K2CO3 aqueous solution. The reaction mixture was heated to about 100° C. and stirred for 12 hours under nitrogen atmosphere. After completion of the reaction, water and toluene were added to the reaction mixture. Subsequently, the organic layer was recovered by solvent extraction operation and dried over sodium sulfate. The solvent was then removed from the organic layer under reduced pressure, and the resulting residue was purified by silica gel column chromatography. The obtained residue was recrystallized with toluene to obtain a white solid product as the claimed novel compound.
- Intermediate A (1.0 eq), Reactant Dn (1.2 eq), Tris(dibenzylitteneacetone)dipalladium(0) (Pd2(dba)3 (0.015eq), and Tricyclohexylphosphinte tetrafiuoroborate [P(Cy)3(HB F4)](0.06eq) were stirred in a mixed solution of DME (0.5 M, v/v=10/1), and 3.0 M of K2CO3 aqueous solution. The reaction mixture was heated to about 90° C. and stirred for 12 hours under nitrogen atmosphere. After completion of the reaction, water and toluene were added to the reaction mixture. Subsequently, the organic layer was recovered by solvent extraction operation and dried over sodium sulfate. The solvent was then removed from the organic layer under reduced pressure, and the resulting residue was purified by silica gel column chromatography. The obtained residue was recrystallized with toluene to obtain a white solid product as the claimed novel compound.
- Intermediates A and Reactants Dn adopted to synthesize
Compounds 1 to 18 were listed in Tables 5-1 and 5-2. -
Compounds 1 to 18 were identified by 1H-NMR and FD-MS, and the chemical structure, yield, formula and mass of each ofCompounds 1 to 12 were also listed in Table 5-1 and 5-2. According toFIGS. 2 to 19 and the results of 1H-NMR, the chemical structures ofCompounds 1 to 18 were identified as follows. -
TABLE 5-1 Intermediates A and Reactant Dn adopted to prepare novel compound by method I and their yields, formulae, and FD-MS data Claimed Compound Intermediate Reactant Chemical Structure of Yield Formula/ A Dn Claimed Compound (%) Mass (M+) A1-B D2 Compound 190 C50H35N3/ 677.83 A1 D7 Compound 365 C33H24N2/ 448.56 A1 D9 Compound 461 C33H24N2/ 448.56 A2-B D2 Compound 682 C50H35N3/ 677.83 A3-B D2 Compound 874 C50H35N3/ 677.83 A4-B D2 Compound 1077 C50H35N3/ 677.83 A2 D23 Compound 1385 C50H35N3/ 677.83 A1 D22 Compound 1488 C44H31N3/ 601.74 A1 D23 Compound 1584 C50H35N3/ 677.83 A2 D22 Compound 1688 C44H31N3/ 601.74 -
TABLE 5-2 Intermediates A and Reactant Dn adopted to prepare novel compound by method II and their yields, formulae, and FD-MS data Claimed Compound Intermediate Reactant Chemical Structure of Yield Formula/ A Dn Claimed Compound (%) Mass (M+) A1-B D1 Compound 276 C50H35N3/ 677.83 A1-B D6 Compound 577 C50H35N3/ 677.83 A2-B D1 Compound 787 C50H35N3/ 677.83 A3-B D1 Compound 976 C50H35N3/ 677.83 A4-B D1 Compound 1180 C50H35N3/ 677.83 A5-B D1 Compound 1283 C50H35N3/ 677.83 A1-B D20 Compound 1775 C44H29N3O/ 615.72 A1-B D21 Compound 1878 C44H29N3O/ 615.72 - In addition to the
Compounds 1 to 18, one person skilled in the art can react any Intermediates A with any Reactants Dn through a reaction mechanism similar to Scheme I and Scheme II to synthesize other desired claimed novel compounds. - Preparation of OLED Devices
- A glass substrate coated with ITO layer (abbreviated in ITO substrate) in a thickness of 1500 Å was placed in distilled water containing a detergent dissolved therein, and was ultrasonically washed. The detergent was a product manufactured by Fischer Co., and the distilled water was distilled water filtered twice through a filter (Millipore Co.). After the ITO layer had been washed for 30 minutes, it was ultrasonically washed twice with distilled water for 10 minutes. After the completion of washing, the glass substrate was ultrasonically washed with isopropyl alcohol, acetone and methanol solvents and then dried, after which it was transported to a plasma cleaner. Then the substrate was cleaned with oxygen plasma for 5 minutes, and then transferred to a vacuum evaporator.
- After that, various organic materials and metal materials were sequentially deposited on the ITO substrate to obtain the OLED device of Examples and Comparative Examples as stated above. The vacuum degree during the deposition was maintained at 1×10−6 to 3×10−7 torr. Herein, the ITO substrate was deposited with a first hole injection layer (HIL-1), a second hole injection layer (HIL-2), a first hole transporting layer (HTL-1), a second hole transporting layer (HTL-2), a blue/green/red emission layer (BEL/GEL/REL), an electron transporting layer (ETL), an electron injection layer (EIL), and a cathode (Cthd).
- Herein, HAT was a material for forming HIL-1 and HIL-2; HI-2 was a material for forming HIL-2; HT-1 and HT-2 were respectively materials for forming HTL-1 and HTL-2; novel compounds of the present invention and commercial ET (BCP) were materials for forming ETL; Liq was a material for forming ETL and EIL. RH/GH/BH were each a host material for forming REL/GEL/BEL, and RD/GD/BD were each a dopant for forming REL/GEL/BEL. The main difference of the OLEDs between the Examples and Comparative Examples was that the ETL of OLED in the following comparative examples were made of BCP, TPBi, or other Comparative Compounds but the ETL of OLED in the following examples was made of the novel compounds of the present invention listed in Tables 5-1 and 5-2. The detailed chemical structures of foresaid commercial materials and other Comparative Compounds used in the OLED devices were listed in Table 6.
- Preparation of Blue OLED Devices
- To prepare the blue OLED device, multiple organic layers were respectively deposited on the ITO substrate according to the sequence as listed in Table 7, and the materials and the thicknesses of the organic layers in blue OLED devices were also listed in Table 7.
-
TABLE 7 coating sequence, materials and thickness of the layers in blue OLED device Coating Sequence Layer Material Thickness 1 HIL-1 HAT 100 Å 2 HIL-2 HI-2 doped with 5.0 wt % of HAT 750 Å 3 HTL-1 HT-1 100 Å 4 HTL-2 HT-2 100 Å 5 BEL BH doped with 3.5 wt % of BD 250 Å 6 ETL Commercial ET/Comparative 250 Å Compound/Novel compounds doped with 35.0 wt % of Liq 7 EIL Liq 15 Å 8 Cthd Al 1500 Å - Preparation of Green OLED Devices
- To prepare the green OLED device, multiple organic layers were respectively deposited on the ITO substrate according to the sequence as listed in Table 8, and the materials and the thicknesses of the organic layers in green OLED devices were also listed in Table 8.
-
TABLE 8 coating sequence, materials and thickness of the layers in green OLED device Coating Sequence Layer Material Thickness 1 HIL-1 HAT 100 Å 2 HIL-2 HI-2 doped with 5.0 wt % of HAT 1300 Å 3 HTL-1 HT-1 100 Å 4 HTL-2 HT-2 100 Å 5 GEL GH doped with 10.0 wt % of GD 400 Å 6 ETL Commercial ET/Comparative 350 Å Compound/Novel compounds doped with 35.0 wt % of Liq 7 EIL Liq 15 Å 8 Cthd Al 1500 Å - Preparation of Red OLED Devices
- To prepare the red OLED device, multiple organic layers were respectively deposited on the ITO substrate according to the sequence as listed in Table 9, and the materials and the thicknesses of the organic layers in red OLED devices were also listed in Table 9.
-
TABLE 9 coating sequence, materials and thickness of the organic layers in red OLED device Coating Sequence Layer Material Thickness 1 HIL-1 HAT 100 Å 2 HIL-2 HI-2 doped with 5.0 wt % of HAT 2100 Å 3 HTL-1 HT-1 100 Å 4 HTL-2 HT-2 100 Å 5 REL RH doped with 3.5 wt % of RD 300 Å 6 ETL Commercial ET/Comparative 350 Å Compound/Novel compounds doped with 35.0 wt % of Liq 7 EIL Liq 15 Å 8 Cthd Al 1500 Å - Performance of OLED Device
- To evaluate the performance of OLED devices, red, green, and blue OLED devices were measured by PR650 as photometer and Keithley 2400 as power supply. Color coordinates (x,y) were determined according to the CIE chromaticity scale (Commission Internationale de L'Eclairage, 1931). The results were shown in Tables 10 to 12. For the blue and red OLED devices, the data of Color coordinates (x,y) were collected at 1000 nits. For the green OLED devices, the data of Color coordinates (x,y) were collected at 3000 nits. For blue OLEDs, the evaluation of lifespan (T85) was defined as a period taken for luminance reduction to 85% of the initial luminance at 2000 nits. The results of blue OLEDs were shown in Table 10.
- For green OLEDs, the evaluation of lifespan (T95) was defined as a period taken for luminance reduction to 95% of the initial luminance at 7000 nits. The results of green OLEDs were shown in Table 11.
- For red OLEDs, the evaluation of lifespan (T90) was defined as a period taken for luminance reduction to 90% of the initial luminance at 6000 nits. The results of red OLEDs were shown in Table 12.
-
TABLE 10 materials of ETL, colors, CIE(x), CIE(y), lifespan (T85) of blue OLED devices of Examples 1 to 18 (El to E18) and Comparative Examples 1 to 3 (C1 to C3) Example No. Material of ET CIE(x) CIE(y) T85 (hrs) E1 Compound 1 0.129 0.16 108.70 E2 Compound 2 0.129 0.162 214.11 E3 Compound 3 0.128 0.158 98.04 E4 Compound 4 0.128 0.161 74.63 E5 Compound 5 0.127 0.163 147.06 E6 Compound 6 0.129 0.163 116.28 E7 Compound 7 0.129 0.162 142.86 E8 Compound 8 0.129 0.158 151.52 E9 Compound 9 0.128 0.158 125.00 E10 Compound 10 0.128 0.165 147.06 E11 Compound 11 0.129 0.157 250.00 E12 Compound 12 0.128 0.163 238.10 E13 Compound 13 0.133 0.156 157.46 E14 Compound 14 0.133 0.154 173.98 E15 Compound 15 0.131 0.157 155.32 E16 Compound 16 0.13 0.155 189.84 E17 Compound 17 0.13 0.169 209.84 E18 Compound 18 0.129 0.163 211.25 C1 BCP 0.129 0.154 18.90 C2 TPBi 0.129 0.154 25.60 C3 Comparative 0.129 0.158 65.79 Compound 1 - As shown in Table 10, the lifespans of blue OLEDs of E1 to E18 are all longer than those of C1 to C3, especially for C3. It demonstrated that adopting the novel compounds of the present invention as the electron transport material can effectively prolong the lifespan of the blue OLED.
-
TABLE 11 materials of ETL, colors, CIE(x), CIE(y), lifespan (T95) of green OLED devices of Examples 19 to 27 (E19 to E27) and Comparative Examples 4 to 7 (C4 to C7) Example No. Material of ET CIE(x) CIE(y) T95 (hrs) E19 Compound 1 0.312 0.64 157.23 E20 Compound 2 0.313 0.64 131.58 E21 Compound 5 0.314 0.639 161.29 E22 Compound 7 0.311 0.641 135.14 E23 Compound 8 0.31 0.641 138.50 E24 Compound 9 0.317 0.638 185.19 E25 Compound 10 0.31 0.64 151.52 E26 Compound 11 0.312 0.639 185.19 E27 Compound 12 0.311 0.641 156.25 C4 BCP 0.308 0.643 29.00 C5 TPBi 0.31 0.641 38.00 C6 Comparative 0.313 0.64 119.90 Compound 1C7 Comparative 0.309 0.641 107.30 Compound 2 - As shown in Table 11, the lifespans of green OLEDs of E19 to E27 are all longer than those of C4 to C7, especially for C6 and C7. It demonstrated that adopting the novel compounds of the present invention as the electron transport material also can effectively prolong the lifespan of the green OLED.
-
TABLE 12 materials of ETL, colors, CIE(x), CIE(y), lifespan (T90) of red OLED devices of Examples 28 to 34 (E28 to E34) and Comparative Examples 8 to 11 (C8 to C11) Example No. Material of ET CIE(x) CIE(y) T90 (hrs) E28 Compound 2 0.66 0.338 228.21 E29 Compound 3 0.658 0.339 140.43 E30 Compound 5 0.66 0.338 234.43 E31 Compound 7 0.659 0.339 212.36 E32 Compound 9 0.66 0.338 248.69 E33 Compound 11 0.658 0.34 260.97 E34 Compound 12 0.658 0.339 260.97 C8 BCP 659 0.339 35.9 C9 TPBi 0.658 0.338 47.8 C10 Comparative 0.661 0.338 108.39 Compound 1C11 Comparative 0.66 0.337 156.99 Compound 2 - As shown in Table 12, the lifespans of red OLEDs of E28 to E34 are all longer than those of C8 to C11, especially for C10 and C11. It demonstrated that adopting the novel compounds of the present invention as the electron transport material also can effectively prolong the lifespan of the red OLED, like the blue and green OLEDs.
- Based on the results shown in Tables 10 to 12, the novel compounds of the present invention can be act as the suitable electron transport material and has the effect of prolonging the lifespan of the red, green, and blue OLEDs.
- Even though numerous characteristics and advantages of the present invention have been set forth in the foregoing description, together with details of the structure and features of the invention, the disclosure is illustrative only. Changes may be made in the details, especially in matters of shape, size, and arrangement of parts within the principles of the invention to the full extent indicated by the broad general meaning of the terms in which the appended claims are expressed.
Claims (20)
1. A compound represented by the following Formula (I):
wherein A1 and A2 each represent a carbon atom; *1 is bonded to one of A1 and A2, and *2 is bonded to the other of A1 and A2;
a is an integer from 1 to 4;
b is an integer from 0 to 3;
L is an arylene group having 6 to 60 carbon atoms;
G is selected from the group consisting of: a heteroaryl group having 3 to 60 ring carbon atoms, an alkyl group having 1 to 40 carbon atoms and substituted with at least one functional group, an alkenyl group having 2 to 40 carbon atoms and substituted with at least one functional group, an alkynyl group having 2 to 40 carbon atoms and substituted with at least one functional group, a cycloalkyl group having 3 to 60 ring carbon atoms and substituted with at least one functional group, a heterocycloalkyl group having 3 to 60 ring carbon atoms and substituted with at least one functional group, an alkoxy group having 1 to 40 carbon atoms and substituted with at least one functional group, an aryl group having 6 to 60 ring carbon atoms and substituted with at least one functional group, an aryloxy group having 6 to 60 ring carbon atoms and substituted with at least one functional group, an alkylsilyl group having 1 to 40 carbon atoms and substituted with at least one functional group, an arylsilyl group having 6 to 60 ring carbon atoms and substituted with at least one functional group, an alkylboron group having 1 to 40 carbon atoms and substituted with at least one functional group, an arylboron group having 6 to 60 ring carbon atoms and substituted with at least one functional group, a phosphine group having 1 to 40 carbon atoms and substituted with at least one functional group, and a phosphine oxide group having 1 to 40 carbon atoms and substituted with at least one functional group, any isomeric groups thereof, and any deuterated analogs thereof, wherein the functional group is selected from the group consisting of: a cyano group, a nitro group, a trifluoromethyl group, a fluoro group, and a chloro group;
c is an integer from 0 to 4;
Y is selected from the group consisting of: a deuterium atom, an unsubstituted aryl group having 6 to 60 ring carbon atoms, an unsubstituted alkyl group having 1 to 12 carbon atoms, an unsubstituted alkenyl group having 2 to 12 carbon atoms, and an unsubstituted alkynyl group having 2 to 12 carbon atoms; and
Z1 and Z2 are each independently an alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 ring carbon atoms, and Z1 and Z2 are the same or different.
2. The compound as claimed in claim 1 , wherein a in Formula (I) is the integer 1.
4. The compound as claimed in claim 1 , wherein the heteroaryl group having 3 to 60 ring carbon atoms represented by G in Formula (I) is selected from the group consisting of: a furyl group, a pyrrolyl group, a thiophenyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group; a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group; an indolyl group, an isoindolyl group, a benzofuranyl group, an isobenzofuranyl group, a benzothiophenyl group, an isobenzothiophenyl group, an indolizinyl group, a quinolizinyl group, a quinolyl group, an isoquinolyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, an indazolyl group, a benzisoxazolyl group, a benzisothiazolyl group; a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a biscarbazolyl group, a coumarinyl group, a chromenyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a phenothiazinyl group, a phenoxazinyl group, an azatriphenylenyl group, a diazatriphenylenyl group, a xanthenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, a benzofuranobenzothiophenyl group, a benzothienobenzothiophenyl group, a dibenzofuranonaphthyl group, a dibenzothienonaphthyl group, a dinaphthothienothiophenyl group, a dinaphtho carbazolyl group, a dibenzo[b,f]azepin group, a tribenzo[b,d,f]azepin group, a dibenzo[b,f]oxepin group, a tribenzo[b,d,f]oxepin group, any isomeric groups thereof, and any deuterated analogs thereof.
5. The compound as claimed in claim 4 , wherein the heteroaryl group having 3 to 60 ring carbon atoms represented by G in Formula (I) is selected from the group consisting of: a furyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a tetrazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyridazinyl group, a pyrimidinyl group, a triazinyl group, an isoindolyl group, an isobenzofuranyl group, an isobenzothiophenyl group, an indolizinyl group, a quinolizinyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, an indazolyl group, a benzisoxazolyl group, a benzisothiazolyl group, a biscarbazolyl group, a coumarinyl group, a chromenyl group, a phenanthridinyl group, an azatriphenylenyl group, a diazatriphenylenyl group, a xanthenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, a benzofuranobenzothiophenyl group, a benzothienobenzothiophenyl group, a dibenzofuranonaphthyl group, a dibenzothienonaphthyl group, a dinaphthothienothiophenyl group, a dinaphtho carbazolyl group, a dibenzo[b,f]azepin group, a tribenzo[b,d,f]azepin group, a dibenzo[b,f]oxepin group, a tribenzo[b,d,f]oxepin group, any isomeric groups thereof, and any deuterated analogs thereof.
6. The compound as claimed in claim 1 , wherein G in Formula (I) is selected from the group consisting of:
wherein o is an integer from 0 to 2; m is an integer from 0 to 3; n is an integer from 0 to 4; and p is an integer from 0 to 5;
wherein R1 to R5 are each independently selected from the group consisting of: a deuterium atom, a halogen group, a cyano group, a nitro group, a trifluoromethyl group, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heterocycloalkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 3 to 30 carbon atoms, an alkoxy group having 1 to 40 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylboron group having 1 to 30 carbon atoms, an arylboron group having 6 to 30 carbon atoms, a phosphine group having 1 to 30 carbon atoms, and a phosphine oxide group having 1 to 30 carbon atoms.
8. The compound as claimed in claim 1 , wherein the aryl group having 6 to 60 ring carbon atoms and substituted with at least one functional group represented by G in Formula (I) is selected from the group consisting of: a phenyl group substituted with the at least one functional group, a biphenyl group substituted with the at least one functional group, a terphenyl group substituted with the at least one functional group, a naphthyl group substituted with the at least one functional group, a phenanthryl group substituted with the at least one functional group, an anthracenyl group substituted with the at least one functional group, a benzanthryl group substituted with the at least one functional group, a fluorenyl group substituted with the at least one functional group, a chrysenyl group substituted with the at least one functional group, a fluoranthenyl group substituted with the at least one functional group, and any deuterated analogs thereof.
9. The compound as claimed in claim 1 , wherein the aryl group having 6 to 60 ring carbon atoms and substituted with at least one functional group represented by G in Formula (I) is selected from the group consisting of:
wherein r is an integer from 1 to 5; s is an integer from 0 to 4; and the sum of r and s is not more than 5;
wherein R1 is selected from the group consisting of: a deuterium atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 30 ring carbon atoms, a heterocycloalkyl group having 3 to 30 ring carbon atoms, an aryl group having 6 to 30 ring carbon atoms, a heteroaryl group having 3 to 30 ring carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryloxy group having 6 to 30 ring carbon atoms, an alkylsilyl group having 1 to 12 carbon atoms, an arylsilyl group having 6 to 30 ring carbon atoms, an alkylboron group having 1 to 12 carbon atoms and an arylboron group having 6 to 30 ring carbon atoms.
10. The compound as claimed in claim 1 , wherein Y is selected from the group consisting of: a deuterium atom, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, an anthracenyl group, a benzanthryl group, a fluorenyl group, a chrysenyl group, a fluoranthenyl group, a deuterated phenyl group, a deuterated biphenyl group, a deuterated terphenyl group, a deuterated naphthyl group, a deuterated phenanthryl group, a deuterated anthracenyl group, a deuterated benzanthryl group, a deuterated fluorenyl group, a deuterated chrysenyl group, and a deuterated fluoranthenyl group.
11. The compound as claimed in claim 1 , wherein b is the integer 0.
16. An organic electronic device, comprising a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises the compound as claimed in claim 1 .
17. The organic electronic device as claimed in claim 16 , wherein the organic electronic device is an organic light emitting device.
18. The organic electronic device as claimed in claim 17 , wherein the organic light emitting device comprises:
a hole injection layer formed on the first electrode;
a hole transport layer formed on the hole injection layer;
an emission layer formed on the hole transport layer;
an electron transport layer formed on the emission layer, wherein the organic layer is the electron transport layer; and
an electron injection layer formed between the electron transport layer and the second electrode.
19. The organic electronic device as claimed in claim 17 , wherein the organic light emitting device comprises:
a hole injection layer formed on the first electrode;
a hole transport layer formed on the hole injection layer;
an emission layer formed on the hole transport layer;
a hole blocking layer formed on the emission layer, wherein the organic layer is the hole blocking layer;
an electron transport layer formed on the hole blocking layer; and
an electron injection layer formed between the electron transport layer and the second electrode.
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US16/429,594 Abandoned US20190372016A1 (en) | 2018-06-05 | 2019-06-03 | Compound and organic electronic device using the same |
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WO2021166596A1 (en) | 2020-02-18 | 2021-08-26 | 日立Astemo株式会社 | Vehicle control device, vehicle control method, and vehicle control system |
CN115745872A (en) * | 2022-09-06 | 2023-03-07 | 常州强力昱镭光电材料有限公司 | Spirofluorene derivative containing seven-membered ring, electron transport material containing the same, and organic electroluminescent element |
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JP6071398B2 (en) * | 2012-10-05 | 2017-02-01 | キヤノン株式会社 | Indeno [1,2-b] phenanthrene compound and organic light-emitting device having the same |
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US11751473B2 (en) | 2016-07-26 | 2023-09-05 | Lg Chem, Ltd. | Organic light emitting element |
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US10693075B2 (en) * | 2016-08-09 | 2020-06-23 | Shanghai Nichem Fine Chemical Co., Ltd. | Spiro compound and organic electronic device comprising the same |
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US11183641B2 (en) | 2021-11-23 |
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KR102170538B1 (en) | 2020-10-28 |
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