WO2013180456A1 - Novel organic electroluminescent compounds and organic electroluminescent device comprising the same - Google Patents
Novel organic electroluminescent compounds and organic electroluminescent device comprising the same Download PDFInfo
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- WO2013180456A1 WO2013180456A1 PCT/KR2013/004688 KR2013004688W WO2013180456A1 WO 2013180456 A1 WO2013180456 A1 WO 2013180456A1 KR 2013004688 W KR2013004688 W KR 2013004688W WO 2013180456 A1 WO2013180456 A1 WO 2013180456A1
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- substituted
- unsubstituted
- alkyl
- compound
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 147
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- -1 triphenylsilyl Chemical group 0.000 claims description 15
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 14
- 229910052805 deuterium Inorganic materials 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000005104 aryl silyl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000005549 heteroarylene group Chemical group 0.000 claims description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000001769 aryl amino group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 4
- 125000006835 (C6-C20) arylene group Chemical group 0.000 claims description 4
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000003367 polycyclic group Chemical group 0.000 claims description 3
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 3
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000005567 fluorenylene group Chemical group 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000005560 phenanthrenylene group Chemical group 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000005550 pyrazinylene group Chemical group 0.000 claims description 2
- 125000005551 pyridylene group Chemical group 0.000 claims description 2
- 125000005576 pyrimidinylene group Chemical group 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 description 57
- 239000010410 layer Substances 0.000 description 53
- 239000000463 material Substances 0.000 description 39
- 238000001308 synthesis method Methods 0.000 description 22
- 239000002019 doping agent Substances 0.000 description 20
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000002347 injection Methods 0.000 description 14
- 239000007924 injection Substances 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- JRCJYPMNBNNCFE-UHFFFAOYSA-N 1,6-dibromopyrene Chemical compound C1=C2C(Br)=CC=C(C=C3)C2=C2C3=C(Br)C=CC2=C1 JRCJYPMNBNNCFE-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 239000007832 Na2SO4 Substances 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- YPCHNZDCUARXNN-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline-6-carbonitrile Chemical compound N1CCCC2=CC(C#N)=CC=C21 YPCHNZDCUARXNN-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
- BSMGLVDZZMBWQB-UHFFFAOYSA-N 2-methyl-1-phenylpropan-1-one Chemical compound CC(C)C(=O)C1=CC=CC=C1 BSMGLVDZZMBWQB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 0 C*(C=Cc1c(-c2ccccc2)c2c3cccc2)c1c3-c1cc(cccc2)c2c2c1cccc2 Chemical compound C*(C=Cc1c(-c2ccccc2)c2c3cccc2)c1c3-c1cc(cccc2)c2c2c1cccc2 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 2
- 229940067157 phenylhydrazine Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000002344 surface layer Substances 0.000 description 2
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 2
- JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical group C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- XHZUPQUVMGRPDC-UHFFFAOYSA-N 1,2,3,4-tetratert-butylperylene Chemical group C1=CC(C2=C(C(C(C)(C)C)=C(C=3C2=C2C=CC=3C(C)(C)C)C(C)(C)C)C(C)(C)C)=C3C2=CC=CC3=C1 XHZUPQUVMGRPDC-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LCAKAXJAQMMVTQ-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-2-phenylbenzene Chemical group C=1C=CC=C(C=2C=CC=CC=2)C=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 LCAKAXJAQMMVTQ-UHFFFAOYSA-N 0.000 description 1
- WTEJYGDMCOWSLV-UHFFFAOYSA-N 1-n,1-n,6-n,6-n-tetraphenylpyrene-1,6-diamine Chemical compound C1=CC=CC=C1N(C=1C2=CC=C3C=CC(=C4C=CC(C2=C43)=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 WTEJYGDMCOWSLV-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- YJLXEKFYZIBUPJ-UHFFFAOYSA-N 2,4-dibromo-6-fluoroaniline Chemical compound NC1=C(F)C=C(Br)C=C1Br YJLXEKFYZIBUPJ-UHFFFAOYSA-N 0.000 description 1
- HLCPWBZNUKCSBN-UHFFFAOYSA-N 2-aminobenzonitrile Chemical compound NC1=CC=CC=C1C#N HLCPWBZNUKCSBN-UHFFFAOYSA-N 0.000 description 1
- FTZQXOJYPFINKJ-UHFFFAOYSA-N 2-fluoroaniline Chemical compound NC1=CC=CC=C1F FTZQXOJYPFINKJ-UHFFFAOYSA-N 0.000 description 1
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 description 1
- NJXPYZHXZZCTNI-UHFFFAOYSA-N 3-aminobenzonitrile Chemical compound NC1=CC=CC(C#N)=C1 NJXPYZHXZZCTNI-UHFFFAOYSA-N 0.000 description 1
- IJQQLTRUDWNWRQ-UHFFFAOYSA-N 4-(2-methylpropanoyl)benzonitrile Chemical compound CC(C)C(=O)C1=CC=C(C#N)C=C1 IJQQLTRUDWNWRQ-UHFFFAOYSA-N 0.000 description 1
- DZUUSHCOMPROCJ-UHFFFAOYSA-N 4-hydrazinylbenzonitrile Chemical compound NNC1=CC=C(C#N)C=C1 DZUUSHCOMPROCJ-UHFFFAOYSA-N 0.000 description 1
- RZCORCDDVSMUID-UHFFFAOYSA-N C(C1)c(cccc2)c2N1c1c(ccc(cc2)c3c(cc4)c2N(c2ccccc2)c2ccccc2)c3c4cc1 Chemical compound C(C1)c(cccc2)c2N1c1c(ccc(cc2)c3c(cc4)c2N(c2ccccc2)c2ccccc2)c3c4cc1 RZCORCDDVSMUID-UHFFFAOYSA-N 0.000 description 1
- CDSIEQNKZNFTHK-UHFFFAOYSA-N CC(C1)C(c(cc2)c(cc3)c4c2ccc2c4c3ccc2N(CC2)c3c2cccc3)=C(C=CC=C2)C2=C1N(c1ccccc1)c1ccccc1 Chemical compound CC(C1)C(c(cc2)c(cc3)c4c2ccc2c4c3ccc2N(CC2)c3c2cccc3)=C(C=CC=C2)C2=C1N(c1ccccc1)c1ccccc1 CDSIEQNKZNFTHK-UHFFFAOYSA-N 0.000 description 1
- HECRQVJEZICILO-UHFFFAOYSA-N CC(C1)C(c2ccc(cc3)c4c2ccc(cc2)c4c3c2N(C2C=CC=CC2C)C2C=CC=CC2C)=CC=C1N1c2ccccc2CCC1 Chemical compound CC(C1)C(c2ccc(cc3)c4c2ccc(cc2)c4c3c2N(C2C=CC=CC2C)C2C=CC=CC2C)=CC=C1N1c2ccccc2CCC1 HECRQVJEZICILO-UHFFFAOYSA-N 0.000 description 1
- SOZKLEKDEMWHLE-UHFFFAOYSA-N CC(C1)C=CC=C1c1c(cccc2)c2c(-c(cc2)cc3c2-c2ccccc2C3(C)C)c2ccccc12 Chemical compound CC(C1)C=CC=C1c1c(cccc2)c2c(-c(cc2)cc3c2-c2ccccc2C3(C)C)c2ccccc12 SOZKLEKDEMWHLE-UHFFFAOYSA-N 0.000 description 1
- VPPUXGFXYBPACE-UHFFFAOYSA-N CC(C1)c2c3c4c1ccc(N(c1ccccc1)c1ccccc1)c4ccc3ccc2N(CCC1)c2c1cccc2 Chemical compound CC(C1)c2c3c4c1ccc(N(c1ccccc1)c1ccccc1)c4ccc3ccc2N(CCC1)c2c1cccc2 VPPUXGFXYBPACE-UHFFFAOYSA-N 0.000 description 1
- GTHNERVYZDHLEE-UHFFFAOYSA-N CC1C(C)CC(N(c2ccccc2)c2c(ccc3ccc(C(C(C)C4)=CC=C4N4c5ccccc5CC4)c(C(C)C4)c33)c3c4cc2)=CC1 Chemical compound CC1C(C)CC(N(c2ccccc2)c2c(ccc3ccc(C(C(C)C4)=CC=C4N4c5ccccc5CC4)c(C(C)C4)c33)c3c4cc2)=CC1 GTHNERVYZDHLEE-UHFFFAOYSA-N 0.000 description 1
- LKLGUHLPSYLAOZ-UHFFFAOYSA-N CC1C(N(CC2)c3ccc(cc4)c5c3ccc(cc3)c5c4c3N(c3cc(F)cc(F)c3)c3cc(F)cc(F)c3)=C2C=CC1 Chemical compound CC1C(N(CC2)c3ccc(cc4)c5c3ccc(cc3)c5c4c3N(c3cc(F)cc(F)c3)c3cc(F)cc(F)c3)=C2C=CC1 LKLGUHLPSYLAOZ-UHFFFAOYSA-N 0.000 description 1
- OHTLACWXLXHUMB-UHFFFAOYSA-N CC1C(N(CCC2)c3ccc(cc4)c5c3ccc(cc3)c5c4c3N(c3ccccc3)c(cc3)ccc3O)=C2C=CC1 Chemical compound CC1C(N(CCC2)c3ccc(cc4)c5c3ccc(cc3)c5c4c3N(c3ccccc3)c(cc3)ccc3O)=C2C=CC1 OHTLACWXLXHUMB-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXSANJRSKATCH-UHFFFAOYSA-N Cc(cc1)ccc1N(c1ccc(C)cc1)c1c(ccc(cc2)c3c(cc4)c2N(CC2)c5c2cccc5)c3c4cc1 Chemical compound Cc(cc1)ccc1N(c1ccc(C)cc1)c1c(ccc(cc2)c3c(cc4)c2N(CC2)c5c2cccc5)c3c4cc1 VEXSANJRSKATCH-UHFFFAOYSA-N 0.000 description 1
- MZPQXSFAZMNOSU-UHFFFAOYSA-N Cc1cc(N(c2cc(C)cc(C)c2)c2c(ccc(c3c4cc5)ccc4N(CC4)c6c4cccc6)c3c5cc2)cc(C)c1 Chemical compound Cc1cc(N(c2cc(C)cc(C)c2)c2c(ccc(c3c4cc5)ccc4N(CC4)c6c4cccc6)c3c5cc2)cc(C)c1 MZPQXSFAZMNOSU-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- KOPBYBDAPCDYFK-UHFFFAOYSA-N Cs2O Inorganic materials [O-2].[Cs+].[Cs+] KOPBYBDAPCDYFK-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- RAGVQHQWLQWIKP-UHFFFAOYSA-N c(cc1)ccc1-c1c(cccc2)c2c(-c2cc3ccccc3cc2)c2ccccc12 Chemical compound c(cc1)ccc1-c1c(cccc2)c2c(-c2cc3ccccc3cc2)c2ccccc12 RAGVQHQWLQWIKP-UHFFFAOYSA-N 0.000 description 1
- HICWKUFWPIBTCN-UHFFFAOYSA-N c(cc1)ccc1-c1c(cccc2)c2c(-c2cccc3c2cccc3)c2c1cccc2 Chemical compound c(cc1)ccc1-c1c(cccc2)c2c(-c2cccc3c2cccc3)c2c1cccc2 HICWKUFWPIBTCN-UHFFFAOYSA-N 0.000 description 1
- FCNCGHJSNVOIKE-UHFFFAOYSA-N c(cc1)ccc1-c1c(cccc2)c2c(-c2ccccc2)c2ccccc12 Chemical compound c(cc1)ccc1-c1c(cccc2)c2c(-c2ccccc2)c2ccccc12 FCNCGHJSNVOIKE-UHFFFAOYSA-N 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- AKUNKIJLSDQFLS-UHFFFAOYSA-M dicesium;hydroxide Chemical compound [OH-].[Cs+].[Cs+] AKUNKIJLSDQFLS-UHFFFAOYSA-M 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
Definitions
- the present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device comprising the same.
- An electroluminescent (EL) device is a self-light-emitting device with the advantage of providing a wider viewing angle, a greater contrast ratio, and a faster response time.
- An organic EL device was first developed by Eastman Kodak, by using small aromatic diamine molecules and aluminum complexes as material for forming a light-emitting layer [ see Appl. Phys. Lett. 51, 913, 1987].
- the organic EL device emits a light by the injection of a charge into an organic film formed between an electron injection electrode (cathode) and a hole injection electrode (anode) and by the extinction of an electron-hole pair.
- the organic EL device has the following advantages: it can be formed onto a flexible transparent substrate, such as plastic; can be driven at a lower voltage, for example, 10 V or less, over a plasma display panel or an inorganic EL display; has relatively low power consumption; and provides good color. Further, the organic EL device provides tricolor light-emission, i.e., green, blue or red light-emission, and thus there is interest from many people as a next generation color display device.
- the most important factor determining properties, such as luminescent efficiency, lifespan, etc., in an organic EL device is the light-emitting material.
- the light-emitting material is required to have the following features: high luminescent quantum yield in a solid state, high movement degree of an electron and a hole, non-breakdown in vacuum deposition, formability of a uniform thin film, and stability.
- the organic EL device is generally composed of a cathode/a hole injection layer (HIL)/a hole transport layer (HTL)/a light-emitting layer (EML)/an electron transport layer (ETL)/an electron injection layer (EIL)/an anode, and green, blue or red light-emitting of the organic EL device can be embodied depending on how to form a light-emitting layer.
- HIL hole injection layer
- HTL hole transport layer
- EML electron transport layer
- EIL electron injection layer
- the light-emitting material is classified into a host material and a dopant material in the functional aspect.
- the light-emitting layer wherein a dopant is doped onto a host, was known.
- an urgent task is the development of an organic EL device having high efficacy and a long operating lifespan.
- the development of highly excellent light-emitting material over conventional light-emitting materials is urgent considering EL properties required in medium- and large-sized OLED panels.
- a blue light-emitting material system by using diphenylvinyl-biphenyl (DPVBi) and a distyryl blue light-emitting material system (Idemitsu Kosan), and blue light-emitting material systems of dinaphthylanthracene and tetra(t-butyl)perylene (Eastman Kodak) were known.
- DPVBi diphenylvinyl-biphenyl
- Idemitsu Kosan distyryl blue light-emitting material system
- Eastman Kodak blue light-emitting material systems of dinaphthylanthracene and tetra(t-butyl)perylene
- the distyryl blue light-emitting material system of Idemitsu Kosan is effective, since it provides a device having 6 lm/W of power efficiency and 30000 or more hours of operating lifespan.
- the system shows the reduction of color purity with the passage of driving time of a device, when it is applied to a full color display, it shows only several thousand hours of lifespan.
- the conventional blue light-emitting materials do not compose a light-emitting layer by using a host-dopant system, and compose a light-emitting layer by using only host compounds or dopant compounds. Thus, it is difficult to commercially use them in terms of color purity and efficiency. Further, credible data for a long lifespan is insufficient.
- blue light-emission shows better luminescent efficiency, but does not satisfy pure blue color, and thus cannot be applied to high quality displays. Further, it has problems in color purity, efficiency and thermal stability. Thus, it is urgent to develop blue light-emitting materials.
- Korean Patent Application Laying-Open No. 10-2011-0027033 discloses an organic EL device comprising anthracene derivatives and amine derivatives
- Korean Patent Application Laying-Open No. 10-2011-0115887 discloses an organic EL device comprising amine-based compounds.
- organic EL devices comprising the compounds disclosed in the publications as a dopant material are not satisfactory in luminescent efficiency and color purity.
- the objective of the present invention is to provide an organic electroluminescent compound, in particular dopant materials, having high luminescent efficiency and a long lifespan and showing blue light-emission having high color purity; and an organic electroluminescent device having high efficiency and a long operating lifespan, comprising the organic electroluminescent compound.
- L 1 and L 2 each independently represent a single bond, a substituted or unsubstituted 5- to 30-membered heteroarylene group, or a substituted or unsubstituted (C6-C30)arylene group;
- X represents a single bond or CR 11 R 12 ;
- Ar 1 and Ar 2 each independently represent a substituted or unsubstituted 5- to 30-membered heteroaryl group, or a substituted or unsubstituted (C6-C30)aryl group;
- R 1 to R 6 each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group; or are linked to an adjacent substituent(s) to form a saturated or unsaturated ring;
- R 7 represents hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 3- to 30-membered heteroaryl group;
- R 11 and R 12 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group; or are linked to an adjacent substituent(s) to form a saturated or unsaturated ring;
- n an integer of 1 or 2; where n is 2, each of R 7 is the same or different; and
- the organic electroluminescent compounds according to the present invention have high luminescent efficiency and a long lifespan, and show blue light-emission having high color purity, over the conventional dopant materials.
- an organic electroluminescent device having high efficiency, a long operating lifespan, and enhanced power consumption efficiency can be prepared by using the organic electroluminescent compounds according to the present invention.
- the present invention relates to an organic electroluminescent compound represented by formula 1 above, an organic electroluminescent material comprising the organic electroluminescent compound, and an organic electroluminescent device comprising the material.
- L 1 and L 2 each independently represent a single bond, a substituted or unsubstituted 5- to 20-membered heteroarylene group, or a substituted or unsubstituted (C6-C20)arylene group; and more preferably a single bond, a 5- to 20-membered heteroarylene group which is unsubstituted or substituted with a (C1-C6) alkyl group, or an unsubstituted (C6-C20)arylene group.
- L 1 and L 2 each independently represent a single bond, phenylene, biphenylene, naphthylene, fluorenylene, phenanthrenylene, pyridylene, pyrazinylene, pyrimidinylene or pyridazinylene.
- X represents a single bond or CR 11 R 12 , in which preferably R 11 and R 12 each independently represent hydrogen or an unsubstituted (C6-C20)aryl group.
- Ar 1 and Ar 2 each independently represent a substituted or unsubstituted 5- to 20-membered heteroaryl group, or a substituted or unsubstituted (C6-C20)aryl group; and more preferably a 5- to 15-membered heteroaryl group which is unsubstituted or substituted with deuterium, a halogen, a cyano group, a hydroxyl group, a (C1-C6)alkyl group, a halo(C1-C6)alkyl group, a (C1-C6)alkoxy group, a (C6-C12)aryl group, a 5- to 15- membered heteroaryl group, a tri(C1-C6)alkylsilyl group, a tri(C6-C12)arylsilyl group, a di(C1-C6)alkyl(C6-C12)arylsilyl group or a (C1-C6)alkyldi(C
- R 1 to R 6 each independently represent hydrogen, a halogen, a cyano group, a substituted or unsubstituted (C1-C10)alkyl group, or a substituted or unsubstituted (C6-C12)aryl group; and more preferably hydrogen, a halogen, a cyano group, an unsubstituted (C1-C10)alkyl group, or a (C6-C12)aryl group which is unsubstituted or substituted with a cyano group.
- R 7 represents hydrogen, or a substituted or unsubstituted (C1-C6)alkyl group; and more preferably hydrogen, or an unsubstituted (C1-C6)alkyl group.
- (C1-C30)alkyl is meant to be a linear or branched alkyl having 1 to 30 carbon atoms, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.
- “(C1-C30) alkoxy” is meant to be a linear or branched alkoxy having 1 to 30 carbon atoms, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methoxy, ethoxy, propoxy, iso-propoxy, 1-ethylpropoxy, etc.
- (C3-C30)cycloalkyl is a mono- or polycyclic hydrocarbon having 3 to 30 carbon atoms, in which the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
- (C6-C30)aryl(ene) is a monocyclic or fused ring derived from an aromatic hydrocarbon having 6 to 30 carbon atoms, in which the number of carbon atoms is preferably 6 to 20, more preferably 6 to 15, and includes phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc.
- Halogen includes F, Cl, Br and I.
- saturated or unsaturated ring is a mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, in which the number of carbon atoms is preferably 5 to 20, more preferably 5 to 12.
- substituted in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or group, i.e., a substituent.
- Substituents of the substituted alkyl group, the substituted alkoxy group, the substituted cycloalkyl group, the substituted heterocycloalkyl group, the substituted aryl(ene) group, and the substituted heteroaryl(ene) group in L 1 and L 2 , Ar 1 and Ar 2 , R 1 to R 7, R 11 and R 12 each independently are at least one selected from the group consisting of deuterium; a halogen; a cyano group; a carboxyl group; a nitro group; a hydroxyl group; a (C1-C30)alkyl group; a halo(C1-C30)alkyl group; a (C2-C30)alkenyl group; a (C2-C
- organic electroluminescent compounds of formula 1 of the present invention include the following compounds:
- TMS represents trimethylsilyl and TPS represents triphenylsilyl.
- organic electroluminescent compounds of formula 1 according to the present invention can be prepared according to the methods known in the art, for example, Suzuki reaction, Ullman reaction, etc.
- organic electroluminescent compounds of formula 1 according to the present invention can be prepared, for example, according to the following reaction scheme 1 or 2.
- L 1 and L 2 , R 1 to R 7 , Ar 1 and Ar 2 , X and n are as defined in formula 1 above, and Hal represents a halogen.
- the present invention further provides an organic electroluminescent material comprising the organic electroluminescent compound of formula 1 above, and an organic electroluminescent device comprising the material.
- the material can be comprised of the organic electroluminescent compound according to the present invention alone, or can further include conventional materials generally used in organic electroluminescent materials.
- the organic electroluminescent device of the present invention may comprise a first electrode, a second electrode, and at least one organic layer between the first and second electrodes, wherein the organic layer comprises at least one organic electroluminescent compound of formula 1 above.
- the organic layer may comprise a light-emitting layer, and may further comprise at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer, and a hole blocking layer.
- the organic layer preferably the light-emitting layers can include at least one organic electroluminescent compound of formula 1 of the present invention. Further, preferably, the organic layer can include a compound represented by the following formula 2 as a host material:
- R 1 and R 18 each independently represent hydrogen, deuterium, a halogen, a cyano group, a hydroxyl group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, (C3-C30) alicyclic or aromatic ring.
- the host compounds of formula 2 above include the following compounds:
- the organic electroluminescent device according to the present invention may further comprise, in addition to the organic electroluminescent compounds represented by formula 1, at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds in the organic layer.
- the organic layer may further comprise, in addition to the organic electroluminescent compounds represented by formula 1, at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides, and organic metals of d-transition elements of the Periodic Table, or at least one complex compound comprising the metal.
- the organic electroluminescent device of the present invention may emit white light by further comprising at least one light-emitting layer which comprises a blue electroluminescent compound, a red electroluminescent compound, or a green electroluminescent compound, besides the organic electroluminescent compound of formula 1 above; and may further include a yellow or orange light-emitting layer, if necessary.
- a surface layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on an inner surface(s) of one or both electrode(s).
- a chalcogenide (includes oxides) layer of silicon or aluminum is placed on an anode surface of an electroluminescent medium layer, and a metal halide layer or metal oxide layer is placed on a cathode surface of an electroluminescent medium layer.
- the surface layer provides operating stability for the organic electroluminescent device.
- the chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.;
- the metal halide includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and the metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
- a mixed region of an electron transport compound and an reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes.
- the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium.
- the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium.
- the oxidative dopant includes various Lewis acids and acceptor compounds; and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
- a reductive dopant layer may be employed as a charge generating layer to prepare an electroluminescent device having two or more electroluminescent layers and emitting white light.
- dry film-forming methods such as vacuum evaporation, sputtering, plasma, ion plating methods, etc.
- wet film-forming methods such as spin coating, dip coating, flow coating methods, etc.
- a thin film is formed by dissolving or dispersing the material constituting each layer in suitable solvents, such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
- suitable solvents such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
- the solvents are not specifically limited as long as the material constituting each layer is soluble or dispersible in the solvents, which do not cause any problems in forming a layer.
- An OLED device was produced using the organic electroluminescent compound according to the present invention.
- a transparent electrode indium tin oxide (ITO) thin film (15 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) device (Samsung Corning, Republic of Korea) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol, and distilled water, sequentially, and then was stored in isopropanol. Then, the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus.
- 4,4’,4”-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine was introduced into a cell of the vacuum vapor depositing apparatus, and then the pressure in the chamber of the apparatus was controlled to 10 -6 torr. Thereafter, an electric current was applied to the cell to evaporate the introduced material, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate.
- N,N’-bis( ⁇ -naphthyl)-N,N’-diphenyl-4,4’-diamine was introduced into another cell of the vacuum vapor depositing apparatus, and was evaporated by applying electric current to the cell, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
- compound H-70 as a host was introduced into one cell of the vacuum vapor depositing apparatus, and compound D-15 of the present invention as a dopant was introduced into another cell.
- the two materials were evaporated at different rates and deposited in a doping amount of 3 wt% of the dopant, based on the total weight of the host and dopant, to form a light-emitting layer having a thickness of 30 nm on the hole transport layer.
- tris(8-hydroxyquinoline)aluminum(III) was introduced into one cell to form an electron transport layer having a thickness of 30 nm on the light-emitting layer.
- an Al cathode having a thickness of 150 nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer.
- All the materials used for producing the OLED device were purified by vacuum sublimation at 10 -6 torr prior to use.
- the produced OLED device showed blue light-emission having a luminance of 1300 cd/m 2 and a current density of 20.0 mA/cm 2 .
- An OLED device was produced in the same manner as in Device Example 1, except for using compound H-34 as a host and compound D-16 as a dopant in a light-emitting material.
- the produced OLED device showed blue light-emission having a luminance of 1050 cd/m 2 and a current density of 17.5 mA/cm 2 .
- An OLED device was produced in the same manner as in Device Example 1, except for using compound H-20 as a host and compound D-77 as a dopant in a light-emitting material.
- the produced OLED device showed blue light-emission having a luminance of 2550 cd/m 2 and a current density of 43.9 mA/cm 2 .
- An OLED device was produced in the same manner as in Device Example 1, except for using compound H-54 as a host and compound D-70 as a dopant in a light-emitting material.
- the produced OLED device showed blue light-emission having a luminance of 620 cd/m 2 , a current density of 15.1 mA/cm 2 , and CIE color space (0.144, 0.085).
- An OLED device was produced in the same manner as in Device Example 1, except for using compound H-15 as a host and compound D-74 as a dopant in a light-emitting material.
- the produced OLED device showed blue light-emission having a luminance of 430 cd/m 2 , a current density of 10.7 mA/cm 2 , and CIE color space (0.146, 0.090).
- a hole injection layer and a hole transport layer were formed, compound H-8 as a luminescent host was introduced into one cell of the vacuum vapor depositing apparatus, and N1,N1,N6,N6-tetraphenylpyrene-1,6-diamine as a dopant was introduced into another cell.
- the two materials were deposited at a rate of 100:1 to form a light-emitting layer having a thickness of 30 nm on the hole transport layer.
- An electron transport layer and an electron injection layer were deposited according to the same manner as in Device Example 1, an Al cathode having a thickness of 150 nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer. Thus, an OLED device was produced.
- the produced OLED device showed blue light-emission having a luminance of 1210 cd/m 2 , a current density of 22.0 mA/cm 2 , and CIE color space (0.145, 0.143).
- the organic electroluminescent compounds of the present invention have luminescent characteristics superior to the conventional materials as seen from Device Examples 1 to 3. Further, as seen from Device Examples 4 and 5, the organic electroluminescent compounds of the present invention show deep blue over the conventional materials in view of CIE color space.
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Abstract
The present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device containing the same. The organic electroluminescent compounds according to the present invention have high luminescent efficiency and a long lifespan, and show blue light-emission having high color purity, and thus an organic electroluminescent device having high efficiency, a long operating lifespan, and enhanced power consumption efficiency can be prepared by using the organic electroluminescent compounds according to the present invention.
Description
The present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device comprising the same.
An electroluminescent (EL) device is a self-light-emitting device with the advantage of providing a wider viewing angle, a greater contrast ratio, and a faster response time. An organic EL device was first developed by Eastman Kodak, by using small aromatic diamine molecules and aluminum complexes as material for forming a light-emitting layer [see Appl. Phys. Lett. 51, 913, 1987].
The organic EL device emits a light by the injection of a charge into an organic film formed between an electron injection electrode (cathode) and a hole injection electrode (anode) and by the extinction of an electron-hole pair. The organic EL device has the following advantages: it can be formed onto a flexible transparent substrate, such as plastic; can be driven at a lower voltage, for example, 10 V or less, over a plasma display panel or an inorganic EL display; has relatively low power consumption; and provides good color. Further, the organic EL device provides tricolor light-emission, i.e., green, blue or red light-emission, and thus there is interest from many people as a next generation color display device.
The most important factor determining properties, such as luminescent efficiency, lifespan, etc., in an organic EL device is the light-emitting material. The light-emitting material is required to have the following features: high luminescent quantum yield in a solid state, high movement degree of an electron and a hole, non-breakdown in vacuum deposition, formability of a uniform thin film, and stability. The organic EL device is generally composed of a cathode/a hole injection layer (HIL)/a hole transport layer (HTL)/a light-emitting layer (EML)/an electron transport layer (ETL)/an electron injection layer (EIL)/an anode, and green, blue or red light-emitting of the organic EL device can be embodied depending on how to form a light-emitting layer.
The light-emitting material is classified into a host material and a dopant material in the functional aspect. Generally, as a structure of the device having the most excellent EL properties, the light-emitting layer, wherein a dopant is doped onto a host, was known. Recently, an urgent task is the development of an organic EL device having high efficacy and a long operating lifespan. In particular, the development of highly excellent light-emitting material over conventional light-emitting materials is urgent considering EL properties required in medium- and large-sized OLED panels.
As conventional blue light-emitting materials, a blue light-emitting material system by using diphenylvinyl-biphenyl (DPVBi) and a distyryl blue light-emitting material system (Idemitsu Kosan), and blue light-emitting material systems of dinaphthylanthracene and tetra(t-butyl)perylene (Eastman Kodak) were known.
Among them, the distyryl blue light-emitting material system of Idemitsu Kosan is effective, since it provides a device having 6 lm/W of power efficiency and 30000 or more hours of operating lifespan. However, since the system shows the reduction of color purity with the passage of driving time of a device, when it is applied to a full color display, it shows only several thousand hours of lifespan.
Further, the conventional blue light-emitting materials do not compose a light-emitting layer by using a host-dopant system, and compose a light-emitting layer by using only host compounds or dopant compounds. Thus, it is difficult to commercially use them in terms of color purity and efficiency. Further, credible data for a long lifespan is insufficient.
In the case that a light-emitting wavelength slightly moves toward a long wavelength, blue light-emission shows better luminescent efficiency, but does not satisfy pure blue color, and thus cannot be applied to high quality displays. Further, it has problems in color purity, efficiency and thermal stability. Thus, it is urgent to develop blue light-emitting materials.
Korean Patent Application Laying-Open No. 10-2011-0027033 discloses an organic EL device comprising anthracene derivatives and amine derivatives, and Korean Patent Application Laying-Open No. 10-2011-0115887 discloses an organic EL device comprising amine-based compounds. However, organic EL devices comprising the compounds disclosed in the publications as a dopant material are not satisfactory in luminescent efficiency and color purity.
The objective of the present invention is to provide an organic electroluminescent compound, in particular dopant materials, having high luminescent efficiency and a long lifespan and showing blue light-emission having high color purity; and an organic electroluminescent device having high efficiency and a long operating lifespan, comprising the organic electroluminescent compound.
The present inventors found that the above objective can be achieved by a compound represented by the following formula 1:
wherein
L1 and L2 each independently represent a single bond, a substituted or unsubstituted 5- to 30-membered heteroarylene group, or a substituted or unsubstituted (C6-C30)arylene group;
X represents a single bond or CR11R12;
Ar1 and Ar2 each independently represent a substituted or unsubstituted 5- to 30-membered heteroaryl group, or a substituted or unsubstituted (C6-C30)aryl group;
R1 to R6 each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group; or are linked to an adjacent substituent(s) to form a saturated or unsaturated ring;
R7 represents hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 3- to 30-membered heteroaryl group;
R11 and R12 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group; or are linked to an adjacent substituent(s) to form a saturated or unsaturated ring;
n represents an integer of 1 or 2; where n is 2, each of R7 is the same or different; and
the heteroarylene group and the heteroaryl group contain at least one hetero atom selected from the group consisting of B, N, O, S, P(=O), Si and P.
The organic electroluminescent compounds according to the present invention have high luminescent efficiency and a long lifespan, and show blue light-emission having high color purity, over the conventional dopant materials. Thus, an organic electroluminescent device having high efficiency, a long operating lifespan, and enhanced power consumption efficiency can be prepared by using the organic electroluminescent compounds according to the present invention.
Hereinafter, the present invention will be described in detail. However, the following description is intended to explain the invention, and is not meant in any way to restrict the scope of the invention.
The present invention relates to an organic electroluminescent compound represented by formula 1 above, an organic electroluminescent material comprising the organic electroluminescent compound, and an organic electroluminescent device comprising the material.
In the organic electroluminescent compound represented by formula 1 above, preferably, L1 and L2 each independently represent a single bond, a substituted or unsubstituted 5- to 20-membered heteroarylene group, or a substituted or unsubstituted (C6-C20)arylene group; and more preferably a single bond, a 5- to 20-membered heteroarylene group which is unsubstituted or substituted with a (C1-C6) alkyl group, or an unsubstituted (C6-C20)arylene group. Specifically, L1 and L2 each independently represent a single bond, phenylene, biphenylene, naphthylene, fluorenylene, phenanthrenylene, pyridylene, pyrazinylene, pyrimidinylene or pyridazinylene.
X represents a single bond or CR11R12, in which preferably R11 and R12 each independently represent hydrogen or an unsubstituted (C6-C20)aryl group.
Preferably, Ar1 and Ar2 each independently represent a substituted or unsubstituted 5- to 20-membered heteroaryl group, or a substituted or unsubstituted (C6-C20)aryl group; and more preferably a 5- to 15-membered heteroaryl group which is unsubstituted or substituted with deuterium, a halogen, a cyano group, a hydroxyl group, a (C1-C6)alkyl group, a halo(C1-C6)alkyl group, a (C1-C6)alkoxy group, a (C6-C12)aryl group, a 5- to 15- membered heteroaryl group, a tri(C1-C6)alkylsilyl group, a tri(C6-C12)arylsilyl group, a di(C1-C6)alkyl(C6-C12)arylsilyl group or a (C1-C6)alkyldi(C6-C12)arylsilyl group, or a (C6-C15) aryl group which is unsubstituted or substituted with deuterium, a halogen, a cyano group, a hydroxyl group, a (C1-C6)alkyl group, a halo(C1-C6)alkyl group, a (C1-C6)alkoxy group, a (C6-C12)aryl group, a 5- to 15- membered heteroaryl group, a tri(C1-C6)alkylsilyl group, a tri(C6-C12)arylsilyl group, a di(C1-C6)alkyl(C6-C12)arylsilyl group or a (C1-C6)alkyldi(C6-C12)arylsilyl group.
Preferably, R1 to R6 each independently represent hydrogen, a halogen, a cyano group, a substituted or unsubstituted (C1-C10)alkyl group, or a substituted or unsubstituted (C6-C12)aryl group; and more preferably hydrogen, a halogen, a cyano group, an unsubstituted (C1-C10)alkyl group, or a (C6-C12)aryl group which is unsubstituted or substituted with a cyano group.
Preferably, R7 represents hydrogen, or a substituted or unsubstituted (C1-C6)alkyl group; and more preferably hydrogen, or an unsubstituted (C1-C6)alkyl group.
Herein, “(C1-C30)alkyl” is meant to be a linear or branched alkyl having 1 to 30 carbon atoms, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. “(C1-C30) alkoxy” is meant to be a linear or branched alkoxy having 1 to 30 carbon atoms, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methoxy, ethoxy, propoxy, iso-propoxy, 1-ethylpropoxy, etc. “(C3-C30)cycloalkyl” is a mono- or polycyclic hydrocarbon having 3 to 30 carbon atoms, in which the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. “3- to 7-membered heterocycloalkyl” is a cycloalkyl having at least one heteroatom selected from the group consisting of B, N, O, S, P(=O), Si and P, preferably O, S and N, and 3 to 7 ring backbone atoms, and includes tetrahydrofurane, pyrrolidine, thiolan, tetrahydropyran, etc. “(C6-C30)aryl(ene)” is a monocyclic or fused ring derived from an aromatic hydrocarbon having 6 to 30 carbon atoms, in which the number of carbon atoms is preferably 6 to 20, more preferably 6 to 15, and includes phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc. “5- to 30-membered heteroaryl(ene)” is an aryl group having at least one, preferably 1 to 4 heteroatom selected from the group consisting of B, N, O, S, P(=O), Si and P, and 5 to 30 ring backbone atoms; is a monocyclic ring, or a fused ring condensed with at least one benzene ring; has preferably 5 to 20, more preferably 5 to 15 ring backbone atoms; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); and includes a monocyclic ring-type heteroaryl including furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl including benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, 9H-carbazolyl, 3-carbazolyl, 9-arylcarbazolyl, 2-carbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, etc. “Halogen” includes F, Cl, Br and I. Further, “saturated or unsaturated ring” is a mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, in which the number of carbon atoms is preferably 5 to 20, more preferably 5 to 12.
Herein, “substituted” in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or group, i.e., a substituent. Substituents of the substituted alkyl group, the substituted alkoxy group, the substituted cycloalkyl group, the substituted heterocycloalkyl group, the substituted aryl(ene) group, and the substituted heteroaryl(ene) group in L1 and L2, Ar1 and Ar2, R1 to R7, R11 and R12 each independently are at least one selected from the group consisting of deuterium; a halogen; a cyano group; a carboxyl group; a nitro group; a hydroxyl group; a (C1-C30)alkyl group; a halo(C1-C30)alkyl group; a (C2-C30)alkenyl group; a (C2-C30)alkynyl group; a (C1-C30)alkoxy group; a (C1-C30)alkylthio group; a (C3-C30)cycloalkyl group; a (C3-C30)cycloalkenyl group; a 3- to 7-membered heterocycloalkyl group; a (C6-C30)aryl group which is unsubstituted or substituted with a 5- to 30-membered heteroaryl group; a (C6-C30)aryloxy group; a (C6-C30)arylthio group; a 5- to 30-membered heteroaryl group which is unsubstituted or substituted with a (C6-C30)aryl group; a tri(C1-C30)alkylsilyl group; a tri(C6-C30)arylsilyl group; a di(C1-C30)alkyl(C6-C30)arylsilyl group; a (C1-C30)alkyldi(C6-C30)arylsilyl group; an amino group; a mono- or di(C1-C30)alkylamino group; a mono- or di(C6-C30)arylamino group; a (C1-C30)alkyl(C6-C30)arylamino group; a (C1-C30)alkylcarbonyl group; a (C1-C30)alkoxycarbonyl group; a (C6-C30)arylcarbonyl group; a di(C6-C30)arylboronyl group; a di(C1-C30)alkylboronyl group; a (C1-C30)alkyl(C6-C30)arylboronyl group; a (C6-C30)aryl(C1-C30)alkyl group; and a (C1-C30)alkyl(C6-C30)aryl group; and preferably at least one selected from the group consisting of deuterium; a halogen; a cyano group; (C1-C30)alkyl group; a halo(C1-C30)alkyl group; a (C6-C30)aryl group; a 5- to 30-membered heteroaryl group; a tri(C1-C30)alkylsilyl group; a tri(C6-C30)arylsilyl group; a di(C1-C30)alkyl(C6-C30)arylsilyl group; a (C1-C30)alkyldi(C6-C30)arylsilyl group; an amino group; a mono- or di(C1-C30)alkylamino group; a mono- or di(C6-C30)arylamino group; a (C1-C30)alkyl(C6-C30)arylamino group; a hydroxyl group; and a (C1-C30)alkoxy group.
The organic electroluminescent compounds of formula 1 of the present invention include the following compounds:
wherein TMS represents trimethylsilyl and TPS represents triphenylsilyl.
The organic electroluminescent compounds of formula 1 according to the present invention can be prepared according to the methods known in the art, for example, Suzuki reaction, Ullman reaction, etc.
The organic electroluminescent compounds of formula 1 according to the present invention can be prepared, for example, according to the following reaction scheme 1 or 2.
[Reaction Scheme 1]
[Reaction Scheme 2]
wherein L1 and L2, R1 to R7, Ar1 and Ar2, X and n are as defined in formula 1 above, and Hal represents a halogen.
The present invention further provides an organic electroluminescent material comprising the organic electroluminescent compound of formula 1 above, and an organic electroluminescent device comprising the material. The material can be comprised of the organic electroluminescent compound according to the present invention alone, or can further include conventional materials generally used in organic electroluminescent materials. The organic electroluminescent device of the present invention may comprise a first electrode, a second electrode, and at least one organic layer between the first and second electrodes, wherein the organic layer comprises at least one organic electroluminescent compound of formula 1 above.
One of the first electrodes and the second electrodes can be an anode and the other can be a cathode. The organic layer may comprise a light-emitting layer, and may further comprise at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer, and a hole blocking layer.
The organic layer, preferably the light-emitting layers can include at least one organic electroluminescent compound of formula 1 of the present invention. Further, preferably, the organic layer can include a compound represented by the following formula 2 as a host material:
wherein
R1 and R18 each independently represent hydrogen, deuterium, a halogen, a cyano group, a hydroxyl group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, (C3-C30) alicyclic or aromatic ring.
The host compounds of formula 2 above include the following compounds:
The organic electroluminescent device according to the present invention may further comprise, in addition to the organic electroluminescent compounds represented by formula 1, at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds in the organic layer.
In the organic electroluminescent device according to the present invention, the organic layer may further comprise, in addition to the organic electroluminescent compounds represented by formula 1, at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4th period, transition metals of the 5th period, lanthanides, and organic metals of d-transition elements of the Periodic Table, or at least one complex compound comprising the metal.
In addition, the organic electroluminescent device of the present invention may emit white light by further comprising at least one light-emitting layer which comprises a blue electroluminescent compound, a red electroluminescent compound, or a green electroluminescent compound, besides the organic electroluminescent compound of formula 1 above; and may further include a yellow or orange light-emitting layer, if necessary.
Preferably, in the organic electroluminescent device according to the present invention, at least one layer (hereinafter, "a surface layer”) selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on an inner surface(s) of one or both electrode(s). Specifically, it is preferred that a chalcogenide (includes oxides) layer of silicon or aluminum is placed on an anode surface of an electroluminescent medium layer, and a metal halide layer or metal oxide layer is placed on a cathode surface of an electroluminescent medium layer. The surface layer provides operating stability for the organic electroluminescent device. Preferably, the chalcogenide includes SiOX(1≤X≤2), AlOX(1≤X≤1.5), SiON, SiAlON, etc.; the metal halide includes LiF, MgF2, CaF2, a rare earth metal fluoride, etc.; and the metal oxide includes Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.
Preferably, in the organic electroluminescent device according to the present invention, a mixed region of an electron transport compound and an reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium. Further, the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium. Preferably, the oxidative dopant includes various Lewis acids and acceptor compounds; and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof. A reductive dopant layer may be employed as a charge generating layer to prepare an electroluminescent device having two or more electroluminescent layers and emitting white light.
In order to form each layer constituting the organic electroluminescent device according to the present invention, dry film-forming methods, such as vacuum evaporation, sputtering, plasma, ion plating methods, etc., or wet film-forming methods, such as spin coating, dip coating, flow coating methods, etc., can be used.
When using a wet film-forming method, a thin film is formed by dissolving or dispersing the material constituting each layer in suitable solvents, such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvents are not specifically limited as long as the material constituting each layer is soluble or dispersible in the solvents, which do not cause any problems in forming a layer.
Hereinafter, the organic electroluminescent compound of the present invention, the preparation method of the compound, and the luminescent properties of the device comprising the compound will be explained in detail with reference to the following examples:
Example 1: Preparation of compound D-15
Preparation
of
compound
1-1
After adding 3-aminobenzonitrile (50.0 g, 423.0 mmol), iodobenzene (39.0 ml, 352.0 mmol), palladium(II) acetate(Pd(OAc)2) (3.9 g), tri-t-butylphosphine (P(t-Bu)3) (8.5 ml) and Cs2CO3 (228.0 g) to toluene (1000.0 ml), the reaction mixture was stirred for 24 hours at 120°C. After completing the reaction, the reaction mixture was slowly cooled to room temperature and H2O was added thereto. The organic layer was extracted with ethyl acetate (EA), the obtained organic layer was dried with Na2SO4 and then was concentrated, and was separated through column chromatography to obtain compound 1-1 (70.0 g, Yield: 85 %).
Preparation of compound 1-2
After adding compound 1-1 (8.0 g, 41.0 mmol), 1,6-dibromopyrene (30.0 g, 83.0 mmol), Cu (4.8 g) and Cs2CO3 (34.0 g) to 1,2-dichlorobenzene (400.0 ml), the reaction mixture was stirred for 19 hours at 200°C. After stirring, H2O was slowly added to the reaction mixture to complete the reaction, the reaction mixture was cooled to room temperature, and H2O was added thereto. The organic layer was extracted with EA, the obtained organic layer was dried with Na2SO4 and then was concentrated, and was separated through column chromatography to obtain compound 1-2 (12.0 g, Yield: 60 %).
Preparation of compound D-15
Compound 1-2 (5.0 g, 10.0 mmol) and 1,2,3,4-tetrahydroquinoline (1.6 ml) were mixed. According to the same synthesis method as Preparation of compound 1-1, compound D-15 (3.8 g, Yield: 69 %) was obtained.
Example 2: Preparation of compound D-76
Preparation
of
compound
2-1
After adding 4-isobutyrylbenzonitrile (6.2 g, 35.7 mmol) and phenylhydrazine (3.8 g, 35.7 mmol) to acetic acid (120.0 ml), the reaction mixture was stirred for 3 hours at 80°C. After cooling the mixture, 1,2-dichloroethane (120.0 ml) was added to the mixture and sodium triacetoxyborohydride (NaBH(OAc)3) (9.8 g, 46.6 mol) was gradually added thereto. After stirring the mixture for 30 minutes at room temperature, H2O was added thereto. The organic layer was extracted with EA, the obtained organic layer was dried with Na2SO4 and then was concentrated, and was separated through column chromatography to obtain compound 2-1 (5.3 g, Yield: 60 %).
Preparation of compound D-76
Compound 1-2 (5.0 g, 10.0 mmol) and compound 2-1 (2.5 g, 20.0 mmol) were mixed. According to the same synthesis method as Preparation of compound 1-1, compound D-76 (4.5 g, Yield: 70 %) was obtained.
Example 3: Preparation of compound D-16
Preparation
of
compound
3-1
2-Fluoroaniline (20.0 g, 180.0 mmol) and iodobenzene (16.7 ml, 150.0 mmol) were mixed. According to the same synthesis method as Preparation of compound 1-1, compound 3-1 (23.0 g) was obtained.
Preparation of compound 3-2
Compound 3-1 (5.0 g, 26.7 mmol) and 1,6-dibromopyrene (20.0 g, 53.4 mmol) were mixed. According to the same synthesis method as Preparation of compound 1-2, compound 3-2 (2.9 g) was obtained.
Preparation of compound D-16
Compound 3-2 (2.9 g, 6.15 mmol) and 1,2,3,4-tetrahydroquinole (0.92 ml, 7.38 mmol) were mixed. According to the same synthesis method as Preparation of compound 1-1, compound D-16 (1.7 g) was obtained.
Example
4:
Preparation
of
compound
D-25
Preparation
of
compound
4-1
After adding 2,4-dibromo-6-fluoroaniline (25.0 g, 92.9 mmol), phenylboronic acid (34.0 g, 278.0 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (10.0 g, 9.29 mmol) and K2CO3 (64.0 g, 464.0 mmol) to a mixed solution of toluene (300.0 ml), ethanol (EtOH) (100.0 ml) and H2O (100.0 ml) and dissolving the reaction mixture, and the mixture was stirred for 7 hours at 120°C. After completing the reaction by slowly adding H2O, the organic layer was extracted with EA, was dried with Na2SO4, and was separated through column chromatography to obtain compound 4-1 (20.0 g).
Preparation of compound 4-2
Compound 4-1 (30.0 g, 113.9 mmol) and iodobenzene (19.3 g, 94.0 mmol) were mixed. According to the same synthesis method as Preparation of compound 1-1, compound 4-2 (23.0 g, Yield: 72 %) was obtained.
Preparation of compound 4-3
Compound 4-2 (10.0 g, 29.4 mmol) and 1,6-dibromopyrene (21.0 g, 58.0 mmol) were mixed. According to the same synthesis method as Preparation of compound 1-2, compound 4-3 (2.2 g, Yield: 12 %) was obtained.
Preparation of compound D-25
Compound 4-3 (5.0 g, 8.0 mmol) and indoline (1.0 ml, 9.6 mmol) were mixed. According to the same synthesis method as Preparation of compound 1-1, compound D-25 (1.0 g, Yield: 43 %) was obtained.
Example
5:
Preparation
of
compound
D-80
Compound 4-3 (5.0 g, 8.0 mmol) and 1,2,3,4-tetrahydroquinoline-6-carbonitrile (1.5 g, 9.6 mmol) were mixed. According to the same synthesis method as Preparation of compound 1-1, compound D-80 (1.0 g, Yield: 40 %) was obtained.
Example 6: Preparation of compound D-74
Preparation
of
compound
6-1
Compound A (3.0 g, 8.6 mmol) and 1,6-dibromopyrene (6.2 g, 17.2 mmol) were mixed. According to the same synthesis method as Preparation of compound 1-2, compound 6-1 (4.0 g, Yield: 60 %) was obtained.
Preparation of compound D-74
Compound 6-1 (4.0 g, 6.4 mmol) and 1,2,3,4-tetrahydroquinoline-6-carbonitrile (1.2 g, 7.7 mmol) were mixed. According to the same synthesis method as Preparation of compound 1-1, compound D-74 (2.2 g, Yield: 50 %) was obtained.
Example 7: Preparation of compound D-75
Compound 1-2 (6.0 g, 12.6 mmol) and 2-phenyl-1H-indole (3.0 g, 15.2 mmol) were mixed. According to the same synthesis method as Preparation of compound 1-1, compound D-75 (2.0 g, Yield: 50 %) was obtained.
Example 8: Preparation of compound D-77
Preparation of compound 8-1
2-methyl-1-phenylpropane-1-one (15.7 ml, 104.0 mmol) and phenylhydrazine (15.0 g, 104.0 mmol) were mixed. According to the same synthesis method as Preparation of compound 2-1, compound 8-1 (12.0 g, Yield: 52 %) was obtained.
Preparation of compound 8-2
Diphenylamine (8.0 g, 47.3 mmol) and 1,6-dibromopyrene (34.0 g, 94.6 mmol) were mixed. According to the same synthesis method as Preparation of compound 1-2, compound 8-2 (10.6 g, Yield: 50 %) was obtained.
Preparation of compound D-77
Compound 8-1 (3.1 g, 13.9 mmol) and compound 8-2 (7.5 g, 16.7 mmol) were mixed. According to the same synthesis method as Preparation of compound 1-1, compound D-77 (12.0 g, Yield: 52 %) was obtained.
Example 9: Preparation of compound D-71
Compound 8-1 (3.1 g, 13.9 mmol) and compound 1-2 (6.0 g, 12.7 mmol) were mixed. According to the same synthesis method as Preparation of compound 1-1, compound D-71 (1.5 g, Yield: 20 %) was obtained.
Example
10:
Preparation
of
compound
D-70
Preparation
of
compound
10-1
2-methyl-1-phenylpropane-1-one (15.0 g, 101.0 mmol) and p-cyanophenylhydrazine (17.1 g, 101.0 mmol) were mixed. According to the same synthesis method as Preparation of compound 2-1, compound 10-1 (7.5 g, Yield: 30 %) was obtained.
Preparation of compound D-70
Compound 10-1 (2.5 g, 10.1 mmol) and compound 1-2 (5.0 g, 10.6 mmol) were mixed. According to the same synthesis method as Preparation of compound 1-1, compound D-70 (1.25 g, Yield: 20 %) was obtained.
Example
11:
Preparation
of
compound
D-91
Compound 1-2 (6.3 g, 13.3 mmol) and 1,2,3,4-tetrahydroquinoline-6-carbonitrile (2.0 g, 12.6 mmol) were mixed. According to the same synthesis method as Preparation of compound 1-1, compound D-91 (5.4 g, Yield: 78 %) was obtained.
Example
12:
Preparation
of
compound
D-22
Preparation
of
compound
12-1
2-Aminobenzonitrile (50.0 g, 423.0 mmol) and iodobenzene (39 ml, 352.0 mmol) were mixed. According to the same synthesis method as Preparation of compound 1-1, compound 12-1 (70.0 g, Yield: 85 %) was obtained.
Preparation of compound 12-2
Compound 12-1 (8.0 g, 41.0 mmol) and 1,6-dibromopyrene (30.0 g, 83.0 mmol) were mixed. According to the same synthesis method as Preparation of compound 1-2, compound 12-2 (12.0 g, Yield: 60 %) was obtained.
Preparation of compound D-22
Compound 12-2 (9.5 g, 20.1 mmol) and indoline (2.0 g, 16.8 mmol) were mixed. According to the same synthesis method as Preparation of compound 1-1, compound D-22 (4.3 g, Yield: 50 %) was obtained.
The physical properties of the compounds of the present invention, which were prepared in Examples 1 to 12, are provided in the Table 1 below:
Table 1
Device Example 1: Production of an OLED device by using
the organic electroluminescent compound according to the present invention
An OLED device was produced using the organic electroluminescent compound according to the present invention. A transparent electrode indium tin oxide (ITO) thin film (15 Ω/sq) on a glass substrate for an organic light-emitting diode (OLED) device (Samsung Corning, Republic of Korea) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol, and distilled water, sequentially, and then was stored in isopropanol. Then, the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus. 4,4’,4”-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine was introduced into a cell of the vacuum vapor depositing apparatus, and then the pressure in the chamber of the apparatus was controlled to 10-6 torr. Thereafter, an electric current was applied to the cell to evaporate the introduced material, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate. Then, N,N’-bis(α-naphthyl)-N,N’-diphenyl-4,4’-diamine was introduced into another cell of the vacuum vapor depositing apparatus, and was evaporated by applying electric current to the cell, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer. Thereafter, compound H-70 as a host was introduced into one cell of the vacuum vapor depositing apparatus, and compound D-15 of the present invention as a dopant was introduced into another cell. The two materials were evaporated at different rates and deposited in a doping amount of 3 wt% of the dopant, based on the total weight of the host and dopant, to form a light-emitting layer having a thickness of 30 nm on the hole transport layer. Then, tris(8-hydroxyquinoline)aluminum(III) was introduced into one cell to form an electron transport layer having a thickness of 30 nm on the light-emitting layer. Then, after depositing lithium quinolate as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 150 nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer. Thus, an OLED device was produced. All the materials used for producing the OLED device were purified by vacuum sublimation at 10-6 torr prior to use.
The produced OLED device showed blue light-emission having a luminance of 1300 cd/m2 and a current density of 20.0 mA/cm2.
Device Example 2: Production of an OLED device by using
the organic electroluminescent compound according to the present invention
An OLED device was produced in the same manner as in Device Example 1, except for using compound H-34 as a host and compound D-16 as a dopant in a light-emitting material.
The produced OLED device showed blue light-emission having a luminance of 1050 cd/m2 and a current density of 17.5 mA/cm2.
Device Example 3: Production of an OLED device by using
the organic electroluminescent compound according to the present invention
An OLED device was produced in the same manner as in Device Example 1, except for using compound H-20 as a host and compound D-77 as a dopant in a light-emitting material.
The produced OLED device showed blue light-emission having a luminance of 2550 cd/m2 and a current density of 43.9 mA/cm2.
Device Example 4: Production of an OLED device by using
the organic electroluminescent compound according to the present invention
An OLED device was produced in the same manner as in Device Example 1, except for using compound H-54 as a host and compound D-70 as a dopant in a light-emitting material.
The produced OLED device showed blue light-emission having a luminance of 620 cd/m2, a current density of 15.1 mA/cm2, and CIE color space (0.144, 0.085).
Device Example 5: Production of an OLED device by using
the organic electroluminescent compound according to the present invention
An OLED device was produced in the same manner as in Device Example 1, except for using compound H-15 as a host and compound D-74 as a dopant in a light-emitting material.
The produced OLED device showed blue light-emission having a luminance of 430 cd/m2, a current density of 10.7 mA/cm2, and CIE color space (0.146, 0.090).
Comparative Example 1: Production of an OLED device
by using conventional light-emitting materials
According to the same manner as in Device Example 1, a hole injection layer and a hole transport layer were formed, compound H-8 as a luminescent host was introduced into one cell of the vacuum vapor depositing apparatus, and N1,N1,N6,N6-tetraphenylpyrene-1,6-diamine as a dopant was introduced into another cell. The two materials were deposited at a rate of 100:1 to form a light-emitting layer having a thickness of 30 nm on the hole transport layer. An electron transport layer and an electron injection layer were deposited according to the same manner as in Device Example 1, an Al cathode having a thickness of 150 nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer. Thus, an OLED device was produced.
The produced OLED device showed blue light-emission having a luminance of 1210 cd/m2, a current density of 22.0 mA/cm2, and CIE color space (0.145, 0.143).
The organic electroluminescent compounds of the present invention have luminescent characteristics superior to the conventional materials as seen from Device Examples 1 to 3. Further, as seen from Device Examples 4 and 5, the organic electroluminescent compounds of the present invention show deep blue over the conventional materials in view of CIE color space.
Claims (7)
- An organic electroluminescent compound represented by the following formula 1:whereinL1 and L2 each independently represent a single bond, a substituted or unsubstituted 5- to 30-membered heteroarylene group, or a substituted or unsubstituted (C6-C30)arylene group;X represents a single bond or CR11R12;Ar1 and Ar2 each independently represent a substituted or unsubstituted 5- to 30-membered heteroaryl group, or a substituted or unsubstituted (C6-C30)aryl group;R1 to R6 each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group; or are linked to an adjacent substituent(s) to form a saturated or unsaturated ring;R7 represents hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 3- to 30-membered heteroaryl group;R11 and R12 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, (C3-C30) alicyclic or aromatic ring;n represents an integer of 1 or 2; where n is 2, each of R7 is the same or different; andthe heteroarylene group and the heteroaryl group contain at least one hetero atom selected from the group consisting of B, N, O, S, P(=O), Si and P.
- The organic electroluminescent compound according to claim 1, wherein the substituents of the substituted alkyl group, the substituted alkoxy group, the substituted cycloalkyl group, the substituted heterocycloalkyl group, the substituted aryl(ene) group, and the substituted heteroaryl(ene) group in L1 and L2, Ar1 and Ar2, R1 to R7, R11 and R12 each independently are at least one selected from the group consisting of deuterium; a halogen; a cyano group; a carboxyl group; a nitro group; a hydroxyl group; a (C1-C30)alkyl group; a halo(C1-C30)alkyl group; a (C2-C30)alkenyl group; a (C2-C30)alkynyl group; a (C1-C30)alkoxy group; a (C1-C30)alkylthio group; a (C3-C30)cycloalkyl group; a (C3-C30)cycloalkenyl group; a 3- to 7-membered heterocycloalkyl group; a (C6-C30)aryl group which is unsubstituted or substituted with a 5- to 30-membered heteroaryl group; a (C6-C30)aryloxy group; a (C6-C30)arylthio group; a 5- to 30-membered heteroaryl group which is unsubstituted or substituted with a (C6-C30)aryl group; a tri(C1-C30)alkylsilyl group; a tri(C6-C30)arylsilyl group; a di(C1-C30)alkyl(C6-C30)arylsilyl group; a (C1-C30)alkyldi(C6-C30)arylsilyl group; an amino group; a mono- or di(C1-C30)alkylamino group; a mono- or di(C6-C30)arylamino group; a (C1-C30)alkyl(C6-C30)arylamino group; a (C1-C30)alkylcarbonyl group; a (C1-C30)alkoxycarbonyl group; a (C6-C30)arylcarbonyl group; a di(C6-C30)arylboronyl group; a di(C1-C30)alkylboronyl group; a (C1-C30)alkyl(C6-C30)arylboronyl group; a (C6-C30)aryl(C1-C30)alkyl group; and a (C1-C30)alkyl(C6-C30)aryl group.
- The organic electroluminescent compound according to claim 1, wherein L1 and L2 each independently represent a single bond, a substituted or unsubstituted 5- to 20-membered heteroarylene group, or a substituted or unsubstituted (C6-C20)arylene group;X represents a single bond or CR11R12, in which R11 and R12 each independently represent hydrogen or an unsubstituted (C6-C20)aryl group;Ar1 and Ar2 each independently represent a substituted or unsubstituted 5- to 20-membered heteroaryl group, or a substituted or unsubstituted (C6-C20)aryl group;R1 to R6 each independently represent hydrogen, a halogen, a cyano group, a substituted or unsubstituted (C1-C10)alkyl group, or a substituted or unsubstituted (C6-C12)aryl group; andR7 represents hydrogen, or a substituted or unsubstituted (C1-C6)alkyl group.
- The organic electroluminescent compound according to claim 3, wherein L1 and L2 each independently represent a single bond, a 5- to 20-membered heteroarylene group which is unsubstituted or substituted with a (C1-C6) alkyl group, or an unsubstituted (C6-C20)arylene group;Ar1 and Ar2 each independently represent a 5- to 15-membered heteroaryl group which is unsubstituted or substituted with deuterium, a halogen, a cyano group, a hydroxyl group, a (C1-C6)alkyl group, a halo(C1-C6)alkyl group, a (C1-C6)alkoxy group, a (C6-C12)aryl group, a 5- to 15- membered heteroaryl group, a tri(C1-C6)alkylsilyl group, a tri(C6-C12)arylsilyl group, a di(C1-C6)alkyl(C6-C12)arylsilyl group or a (C1-C6)alkyldi(C6-C12)arylsilyl group, or a (C6-C15) aryl group which is unsubstituted or substituted with deuterium, a halogen, a cyano group, a hydroxyl group, a (C1-C6)alkyl group, a halo(C1-C6)alkyl group, a (C1-C6)alkoxy group, a (C6-C12)aryl group, a 5- to 15- membered heteroaryl group, a tri(C1-C6)alkylsilyl group, a tri(C6-C12)arylsilyl group, a di(C1-C6)alkyl(C6-C12)arylsilyl group or a (C1-C6)alkyldi(C6-C12)arylsilyl group;R1 to R6 each independently represent hydrogen, a halogen, a cyano group, an unsubstituted (C1-C10)alkyl group, or a (C6-C12)aryl group which is unsubstituted or substituted with a cyano group; andR7 represents hydrogen, or an unsubstituted (C1-C6)alkyl group.
- The organic electroluminescent compound according to claim 4, wherein wherein L1 and L2 each independently represent a single bond, phenylene, biphenylene, naphthylene, fluorenylene, phenanthrenylene, pyridylene, pyrazinylene, pyrimidinylene or pyridazinylene.
- An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1.
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KR10-2012-0057557 | 2012-05-30 | ||
KR1020120057557A KR20130134205A (en) | 2012-05-30 | 2012-05-30 | Novel organic electroluminescence compounds and organic electroluminescence device containing the same |
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Cited By (6)
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WO2014088352A1 (en) * | 2012-12-06 | 2014-06-12 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compounds and organic electroluminescent device comprising the same |
CN108203407A (en) * | 2017-12-20 | 2018-06-26 | 李现伟 | Pyrene class electroluminescent organic material, luminescent device and display |
US11581487B2 (en) | 2017-04-26 | 2023-02-14 | Oti Lumionics Inc. | Patterned conductive coating for surface of an opto-electronic device |
US11730012B2 (en) | 2019-03-07 | 2023-08-15 | Oti Lumionics Inc. | Materials for forming a nucleation-inhibiting coating and devices incorporating same |
US11751415B2 (en) | 2018-02-02 | 2023-09-05 | Oti Lumionics Inc. | Materials for forming a nucleation-inhibiting coating and devices incorporating same |
US11985841B2 (en) | 2020-12-07 | 2024-05-14 | Oti Lumionics Inc. | Patterning a conductive deposited layer using a nucleation inhibiting coating and an underlying metallic coating |
Families Citing this family (2)
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WO2016060463A2 (en) * | 2014-10-14 | 2016-04-21 | 주식회사 동진쎄미켐 | Novel compound and organic light-emitting element comprising same |
WO2018110887A1 (en) * | 2016-12-14 | 2018-06-21 | 주식회사 엘지화학 | Heterocyclic compound, and organic light-emitting element comprising same |
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KR20070105081A (en) * | 2006-04-25 | 2007-10-30 | 엘지전자 주식회사 | Organic electroluminescence devices |
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Publication number | Priority date | Publication date | Assignee | Title |
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WO2014088352A1 (en) * | 2012-12-06 | 2014-06-12 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compounds and organic electroluminescent device comprising the same |
US11581487B2 (en) | 2017-04-26 | 2023-02-14 | Oti Lumionics Inc. | Patterned conductive coating for surface of an opto-electronic device |
CN108203407A (en) * | 2017-12-20 | 2018-06-26 | 李现伟 | Pyrene class electroluminescent organic material, luminescent device and display |
US11751415B2 (en) | 2018-02-02 | 2023-09-05 | Oti Lumionics Inc. | Materials for forming a nucleation-inhibiting coating and devices incorporating same |
US11730012B2 (en) | 2019-03-07 | 2023-08-15 | Oti Lumionics Inc. | Materials for forming a nucleation-inhibiting coating and devices incorporating same |
US11985841B2 (en) | 2020-12-07 | 2024-05-14 | Oti Lumionics Inc. | Patterning a conductive deposited layer using a nucleation inhibiting coating and an underlying metallic coating |
Also Published As
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TW201402780A (en) | 2014-01-16 |
KR20130134205A (en) | 2013-12-10 |
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