KR101306531B1 - New compound and organic light emitting device using the same - Google Patents
New compound and organic light emitting device using the same Download PDFInfo
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- KR101306531B1 KR101306531B1 KR1020090002318A KR20090002318A KR101306531B1 KR 101306531 B1 KR101306531 B1 KR 101306531B1 KR 1020090002318 A KR1020090002318 A KR 1020090002318A KR 20090002318 A KR20090002318 A KR 20090002318A KR 101306531 B1 KR101306531 B1 KR 101306531B1
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- KR
- South Korea
- Prior art keywords
- group
- substituted
- unsubstituted
- groups
- alkenyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 60
- 239000011368 organic material Substances 0.000 claims abstract description 30
- 238000002347 injection Methods 0.000 claims abstract description 19
- 239000007924 injection Substances 0.000 claims abstract description 19
- -1 indole compound Chemical class 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims description 63
- 125000000217 alkyl group Chemical group 0.000 claims description 58
- 238000000034 method Methods 0.000 claims description 58
- 125000001424 substituent group Chemical group 0.000 claims description 56
- 125000003342 alkenyl group Chemical group 0.000 claims description 54
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 52
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 51
- 125000000623 heterocyclic group Chemical group 0.000 claims description 46
- 125000003545 alkoxy group Chemical group 0.000 claims description 43
- 125000002560 nitrile group Chemical group 0.000 claims description 43
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 36
- 125000005264 aryl amine group Chemical group 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 32
- 150000002367 halogens Chemical class 0.000 claims description 32
- 239000000126 substance Substances 0.000 claims description 26
- 125000005842 heteroatom Chemical group 0.000 claims description 22
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 19
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 13
- 229910052698 phosphorus Inorganic materials 0.000 claims description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
- 230000005525 hole transport Effects 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 125000005566 carbazolylene group Chemical group 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 125000005567 fluorenylene group Chemical group 0.000 claims description 3
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 2
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 2
- 235000021286 stilbenes Nutrition 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 229910000077 silane Inorganic materials 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 31
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 156
- 239000010410 layer Substances 0.000 description 73
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 16
- YLDFTMJPQJXGSS-UHFFFAOYSA-N 6-bromo-2-naphthol Chemical compound C1=C(Br)C=CC2=CC(O)=CC=C21 YLDFTMJPQJXGSS-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000002474 experimental method Methods 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000012153 distilled water Substances 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 0 CC1C(C)C(C)(C)C*1 Chemical compound CC1C(C)C(C)(C)C*1 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 4
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- GTDQGKWDWVUKTI-UHFFFAOYSA-N o-aminoacetophenone Chemical class CC(=O)C1=CC=CC=C1N GTDQGKWDWVUKTI-UHFFFAOYSA-N 0.000 description 4
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- AJYDOCCGNIBJBY-UHFFFAOYSA-N 2,7-dibromo-9,9-diphenylfluorene Chemical compound C12=CC(Br)=CC=C2C2=CC=C(Br)C=C2C1(C=1C=CC=CC=1)C1=CC=CC=C1 AJYDOCCGNIBJBY-UHFFFAOYSA-N 0.000 description 3
- ZIRVQSRSPDUEOJ-UHFFFAOYSA-N 9-bromoanthracene Chemical compound C1=CC=C2C(Br)=C(C=CC=C3)C3=CC2=C1 ZIRVQSRSPDUEOJ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- SDEAGACSNFSZCU-UHFFFAOYSA-N (3-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(Cl)=C1 SDEAGACSNFSZCU-UHFFFAOYSA-N 0.000 description 2
- HYGLETVERPVXOS-UHFFFAOYSA-N 1-bromopyrene Chemical compound C1=C2C(Br)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 HYGLETVERPVXOS-UHFFFAOYSA-N 0.000 description 2
- APSMUYYLXZULMS-UHFFFAOYSA-N 2-bromonaphthalene Chemical compound C1=CC=CC2=CC(Br)=CC=C21 APSMUYYLXZULMS-UHFFFAOYSA-N 0.000 description 2
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- AQTMWALWRINUMZ-UHFFFAOYSA-N Brc(c1c2ccc(Br)c1)c1[n]2c(-c2ccccc2)nc2c1cccc2 Chemical compound Brc(c1c2ccc(Br)c1)c1[n]2c(-c2ccccc2)nc2c1cccc2 AQTMWALWRINUMZ-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- IVVTVUUKHICUPF-UHFFFAOYSA-N OS(c1ccccc1)O Chemical compound OS(c1ccccc1)O IVVTVUUKHICUPF-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- FIFQMVZNXWAQGE-UHFFFAOYSA-N c(cc1)ccc1-c([n]1c2c3cccc2)nc(cccc2)c2c1c3-c1cccc(-c2ccc(cc3)c4c2ccc2c4c3ccc2)c1 Chemical compound c(cc1)ccc1-c([n]1c2c3cccc2)nc(cccc2)c2c1c3-c1cccc(-c2ccc(cc3)c4c2ccc2c4c3ccc2)c1 FIFQMVZNXWAQGE-UHFFFAOYSA-N 0.000 description 2
- ZJAXLHNKLIHWCO-UHFFFAOYSA-N c(cc1)ccc1-c(c1c2cccc1)c1[n]2c(-c(cc2)ccc2-c(cc2)ccc2-c(cc2)cc(c3cc(-c4ccccc4)ccc33)c2[n]3-c2ccccc2)nc2c1cccc2 Chemical compound c(cc1)ccc1-c(c1c2cccc1)c1[n]2c(-c(cc2)ccc2-c(cc2)ccc2-c(cc2)cc(c3cc(-c4ccccc4)ccc33)c2[n]3-c2ccccc2)nc2c1cccc2 ZJAXLHNKLIHWCO-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229940067157 phenylhydrazine Drugs 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CTPUUDQIXKUAMO-UHFFFAOYSA-N 1-bromo-3-iodobenzene Chemical compound BrC1=CC=CC(I)=C1 CTPUUDQIXKUAMO-UHFFFAOYSA-N 0.000 description 1
- NXYICUMSYKIABQ-UHFFFAOYSA-N 1-iodo-4-phenylbenzene Chemical group C1=CC(I)=CC=C1C1=CC=CC=C1 NXYICUMSYKIABQ-UHFFFAOYSA-N 0.000 description 1
- VTSDGYDTWADUJQ-UHFFFAOYSA-N 2-bromoanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Br)=CC=C3C(=O)C2=C1 VTSDGYDTWADUJQ-UHFFFAOYSA-N 0.000 description 1
- TUCRZHGAIRVWTI-UHFFFAOYSA-N 2-bromothiophene Chemical compound BrC1=CC=CS1 TUCRZHGAIRVWTI-UHFFFAOYSA-N 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- WHIHIKVIWVIIER-UHFFFAOYSA-N 3-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(Cl)=C1 WHIHIKVIWVIIER-UHFFFAOYSA-N 0.000 description 1
- NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 1
- CZPOKTBIKWSWIP-UHFFFAOYSA-N 6-bromonaphthalene-2-carbonyl chloride Chemical compound C1=C(Br)C=CC2=CC(C(=O)Cl)=CC=C21 CZPOKTBIKWSWIP-UHFFFAOYSA-N 0.000 description 1
- HVDNGWZPFMLMHZ-UHFFFAOYSA-N Brc(c1c2cccc1)c1[n]2c(-c2ccccc2)nc2c1cccc2 Chemical compound Brc(c1c2cccc1)c1[n]2c(-c2ccccc2)nc2c1cccc2 HVDNGWZPFMLMHZ-UHFFFAOYSA-N 0.000 description 1
- KUBSCXXKQGDPPD-UHFFFAOYSA-N Brc(cc1c2c3cccc2)ccc1[n]3-c1ccccc1 Chemical compound Brc(cc1c2c3cccc2)ccc1[n]3-c1ccccc1 KUBSCXXKQGDPPD-UHFFFAOYSA-N 0.000 description 1
- WHGGVVHVBFMGSG-UHFFFAOYSA-N Brc1c(cccc2)c2c(-c2ccccc2)c2c1cccc2 Chemical compound Brc1c(cccc2)c2c(-c2ccccc2)c2c1cccc2 WHGGVVHVBFMGSG-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 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
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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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
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Abstract
본 발명은 하기 화학식 1로 표시되는 화합물 및 상기 화합물을 이용한 유기 발광 소자에 관한 것으로서, 본 발명의 신규 화합물은 유기 발광 소자의 수명, 효율, 전기 화학적 안정성 및 열적 안정성을 크게 향상시킬 수 있다.The present invention relates to a compound represented by the following Formula 1 and an organic light emitting device using the compound, the novel compound of the present invention can greatly improve the lifespan, efficiency, electrochemical stability and thermal stability of the organic light emitting device.
[화학식 1][Formula 1]
유기 발광 소자, 유기물층, 전자주입물질, 전자수송물질, 발광물질, 인돌 화합물, 퀴나졸린 화합물 Organic light emitting device, organic material layer, electron injection material, electron transport material, light emitting material, indole compound, quinazoline compound
Description
본 발명은 유기 발광 소자의 수명, 효율, 전기 화학적 안정성 및 열적 안정성을 크게 향상시킬 수 있는 신규 화합물 및 상기 화합물이 유기화합물 층에 포함되어 있는 유기 발광 소자에 관한 것이다.The present invention relates to a novel compound capable of greatly improving the lifespan, efficiency, electrochemical stability and thermal stability of an organic light emitting device, and an organic light emitting device in which the compound is included in an organic compound layer.
유기 발광 현상은 특정 유기 분자의 내부 프로세스에 의하여 전류가 가시광으로 전환되는 예의 하나이다. 유기 발광 현상의 원리는 다음과 같다. 양극과 음극 사이에 유기물 층을 위치시켰을 때 두 전극 사이에 전압을 걸어주게 되면 음극과 양극으로부터 각각 전자와 정공이 유기물 층으로 주입된다. 유기물 층으로 주입된 전자와 정공은 재결합하여 엑시톤(exciton)을 형성하고, 이 엑시톤이 다시 바닥 상태로 떨어지면서 빛이 나게 된다. 이러한 원리를 이용하는 유기 발광소자는 일반적으로 음극과 양극 및 그 사이에 위치한 유기물층, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층을 포함하는 유기물 층으로 구성될 수 있다.The organic light emission phenomenon is one example in which current is converted into visible light by an internal process of a specific organic molecule. The principle of organic luminescence phenomenon is as follows. When the organic layer is placed between the anode and the cathode, a voltage is applied between the two electrodes to inject electrons and holes from the cathode and the anode into the organic layer, respectively. The electrons and holes injected into the organic layer recombine to form excitons, which then fall back to the ground to shine. An organic light emitting device using this principle may generally be composed of an organic material layer including a cathode, an anode, and an organic material layer disposed therebetween, such as a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer.
유기 발광 소자에서 사용되는 물질로는 순수 유기 물질 또는 유기 물질과 금속이 착물을 이루는 착화합물이 대부분을 차지하고 있으며, 용도에 따라 정공주입 물질, 정공수송 물질, 발광 물질, 전자수송 물질, 전자주입 물질 등으로 구분될 수 있다. 여기서, 정공주입 물질이나 정공수송 물질로는 p-타입의 성질을 가지는 유기 물질, 즉 쉽게 산화가 되고 산화시에 전기화학적으로 안정한 상태를 가지는 유기물이 주로 사용되고 있다. 한편, 전자주입 물질이나 전자수송 물질로는 n-타입 성질을 가지는 유기 물질, 즉 쉽게 환원이 되고 환원시에 전기화학적으로 안정한 상태를 가지는 유기물이 주로 사용되고 있다. 발광층 물질로는 p-타입 성질과 n-타입 성질을 동시에 가진 물질, 즉 산화와 환원 상태에서 모두 안정한 형태를 갖는 물질이 바람직하며, 엑시톤이 형성되었을 때 이를 빛으로 전환하는 발광 효율이 높은 물질이 바람직하다.Most of the materials used in the organic light emitting device are pure organic materials or complex compounds in which organic materials and metals are complexed, and depending on the purpose, hole injection materials, hole transport materials, light emitting materials, electron transport materials, electron injection materials, etc. It can be divided into. Here, as the hole injection material or the hole transport material, an organic material having a p-type property, that is, an organic material which is easily oxidized and has an electrochemically stable state during oxidation, is mainly used. On the other hand, as an electron injecting material or an electron transporting material, an organic material having an n-type property, that is, an organic material that is easily reduced and electrochemically stable when being reduced is mainly used. As the light emitting layer material, a material having both a p-type property and an n-type property, that is, a material having both a stable form in oxidation and in a reduced state is preferable, and a material having a high luminous efficiency for converting an exciton into light desirable.
위에서 언급한 외에, 유기 발광 소자에서 사용되는 물질은 다음과 같은 성질을 추가적으로 갖는 것이 바람직하다. In addition to the above, it is preferable that the material used in the organic light emitting device further has the following properties.
저전압 구동 가능한 고효율의 유기 발광 소자를 얻기 위해서는 유기 발광 소자 내로 주입된 정공 또는 전자들이 원활하게 발광층으로 전달되는 동시에, 주입된 정공과 전자들이 발광층 밖으로 빠져나가지 않도록 하여야 한다. 이를 위해서 유기 발광 소자에 사용되는 물질은 적절한 밴드갭(band gap)과 HOMO 또는 LUMO 에너지 준위를 가져야 한다. 현재 전자수송층 물질로 주로 사용되는 Alq3는 충분히 높은 HOMO 에너지 준위를 갖지 못하여, HOMO 에너지 준위가 상대적으론 높은 BAlq층을 더 사용하여야 하기 때문에 공정 및 유기 발광 소자 제조에 어려움이 있다.In order to obtain a high-efficiency organic light emitting device capable of driving a low voltage, holes or electrons injected into the organic light emitting device should be smoothly transferred to the light emitting layer, and the injected holes and electrons should not escape out of the light emitting layer. For this purpose, the material used in the organic light emitting device should have an appropriate band gap and a HOMO or LUMO energy level. Alq3, which is mainly used as an electron transport layer material, does not have a sufficiently high HOMO energy level, and thus, it is difficult to manufacture a process and an organic light emitting device because a BAlq layer having a relatively high HOMO energy level must be used.
이외에도 유기 발광 소자에서 사용되는 물질은 화학적 안정성, 전하이동도, 전극이나 인접한 층과의 계면 특성 등이 우수하여야 한다. 즉, 유기 발광소자에서 사용되는 물질은 수분이나 산소에 의한 물질의 변형이 적어야 한다. 또한, 적절한 정공 또는 전자 이동도를 가짐으로써 유기 발광 소자의 발광층에서 정공과 전자의 밀도가 균형을 이루도록 하여 엑시톤 형성을 극대화할 수 있어야 한다. 그리고, 소자의 안정성을 위해 금속 또는 금속 산화물을 포함한 전극과의 계면을 좋게 할 수 있어야 한다.In addition, materials used in organic light emitting devices should have excellent chemical stability, charge mobility, and interface characteristics with electrodes or adjacent layers. That is, the material used in the organic light emitting device should be less deformation of the material by moisture or oxygen. In addition, by having appropriate hole or electron mobility, it is necessary to maximize the formation of excitons by balancing the density of holes and electrons in the light emitting layer of the organic light emitting device. And, for the stability of the device, the interface with the electrode including the metal or the metal oxide should be good.
따라서, 당 기술 분야에서는 상기와 같은 요건을 갖춘 유기물의 개발이 지속적으로 요구되고 있다.Therefore, there is a continuous need in the art for the development of organic materials having the above requirements.
본 발명은 상기와 같은 종래 기술의 문제점을 해결하기 위한 것으로, 본 발명의 목적은 유기 발광 소자에서 사용 가능한 물질에 요구되는 조건, 예컨대 적절한 에너지 준위, 전기 화학적 안정성 및 열적 안정성 등을 만족시킬 수 있으며, 치환기에 따라 유기 발광 소자에서 요구되는 다양한 역할을 할 수 있는 화학 구조를 갖는 헤테로 화합물 유도체 및 이를 포함하는 유기 발광 소자를 제공하는 것이다.The present invention is to solve the problems of the prior art as described above, an object of the present invention is to satisfy the conditions required for the material that can be used in the organic light emitting device, such as the appropriate energy level, electrochemical stability and thermal stability To provide a hetero compound derivative having a chemical structure that can play a variety of roles required in the organic light emitting device according to the substituent, and an organic light emitting device comprising the same.
상기 목적을 달성하기 위한 본 발명의 일 측면은 하기 화학식 1로 표시되는 화합물을 제공한다.One aspect of the present invention for achieving the above object provides a compound represented by the following formula (1).
[화학식 1][Formula 1]
상기 화학식 1에 있어서, In Formula 1,
R1 내지 R10은 각각 독립적으로, 수소; 중수소; 할로겐기; 알킬기, 알케닐기, 알콕시기, 치환 또는 비치환된 아릴기, 치환 또는 비치환된 아릴알킬기, 치환 또는 비치환된 아릴알케닐기, 치환 또는 비치환된 헤테로 고리기, 니트릴기 및 아세틸렌 기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환된 C1 -50의 알킬기; 할로겐기, 알킬기, 알케닐기, 알콕시기, 치환 또는 비치환된 아릴기, 치환 또는 비치환된 아릴알킬기, 치환 또는 비치환된 아릴알케닐기, 치환 또는 비치환된 헤테로 고리기, 니트릴기 및 아세틸렌기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환된 C1 -40의 알콕시기; 할로겐기, 알킬기, 알케닐기, 알콕시기, 치환 또는 비치환된 아릴기, 치환 또는 비치환된 아릴알킬기, 치환 또는 비치환된 아릴알케닐기, 치환 또는 비치환된 헤테로 고리기, 니트릴기 및 아세틸렌기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환된 C2 -50의 알케닐기; 할로겐기, 알킬기, 알케닐기, 알콕시기, 치환 또는 비치환된 아릴아민기, 치환 또는 비치환된 아릴기, 치환 또는 비치환된 아릴알킬기, 치환 또는 비치환된 아릴알케닐기, 치환 또는 비치환된 헤테로 고리기, 니트릴기, 실란기, 치환 또는 비치환된 플루오레닐기, 치환 또는 비치환된 비스스피로플루오레닐기, 치환 또는 비치환된 카바졸릴기 및 아세틸렌기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환된 C6 -60의 아릴기; 할로겐기, 알킬기, 알케닐기, 알콕시기, 치환 또는 비치환된 아릴아민기, 치환 또는 비치환된 아릴기, 치환 또는 비치환된 아릴알킬기, 치환 또는 비치환된 아릴알케닐기, 치환 또는 비치환된 헤테로 고리기, 니트릴기 및 아세틸렌기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환된 C2 -40의 아세틸기; 할로겐기, 알킬기, 알케닐기, 알콕시기, 치환 또는 비치환된 아릴아민기, 치환 또는 비치환된 아릴기, 치환 또는 비치환된 아릴알킬기, 치환 또는 비치환된 아릴알케닐기, 치환 또는 비치환된 헤테로 고리기, 니트릴기 및 아세틸렌기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환되고 이종원소로 O, N, S 또는 P를 갖는 C3 -60의 헤테로 고리기; 알킬기, 알케닐기, 치환 또는 비치환된 아릴기, 치환 또는 비치환된 아릴알킬기, 치환 또는 비치환된 아릴알케닐기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환된 아민기; 알킬기, 알케닐기 치환 또는 비치환된 아릴기, 치환 또는 비치환된 아릴알킬기, 치환 또는 비치환된 아릴알케닐기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환된 플루오레닐기; 비스스피로플루오레닐기; 할로겐기, 알킬기, 알케닐기, 알콕시기, 치환 또는 비치환된 아릴아민기, 치환 또는 비치환된 아릴기, 치환 또는 비치환된 아릴알킬기, 치환 또는 비치환된 아릴알케닐기, 치환 또는 비치환된 헤테로 고리기, 니트릴기 및 아세틸렌기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환된 카바졸릴기; 니트릴기; 시아노기; 니트로기; 아미드기; 에스테르기; 실란기 및 게르마늄기로 이루어진 군에서 선택되며 여기서 이들은 서로 인접하는 기와 지방족 또는 헤테로의 축합 고리를 형성할 수 있다.R 1 to R 10 are each independently hydrogen; heavy hydrogen; A halogen group; In the group consisting of an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, a nitrile group and an acetylene group alkyl substituted or unsubstituted C 1 -50 with at least one substituent group selected; Halogen, alkyl, alkenyl, alkoxy, substituted or unsubstituted aryl groups, substituted or unsubstituted arylalkyl groups, substituted or unsubstituted arylalkenyl groups, substituted or unsubstituted heterocyclic groups, nitrile groups and acetylene groups alkoxy group, a substituted or unsubstituted C 1 -40 with at least one substituent selected from the group consisting of; Halogen, alkyl, alkenyl, alkoxy, substituted or unsubstituted aryl groups, substituted or unsubstituted arylalkyl groups, substituted or unsubstituted arylalkenyl groups, substituted or unsubstituted heterocyclic groups, nitrile groups and acetylene groups an alkenyl group of a substituted or unsubstituted C 2 -50 with one or more substituents selected from the group consisting of; Halogen, alkyl, alkenyl, alkoxy, substituted or unsubstituted arylamine groups, substituted or unsubstituted aryl groups, substituted or unsubstituted arylalkyl groups, substituted or unsubstituted arylalkenyl groups, substituted or unsubstituted At least one substituent selected from the group consisting of a heterocyclic group, a nitrile group, a silane group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted bisspirofluorenyl group, a substituted or unsubstituted carbazolyl group, and an acetylene group A substituted or unsubstituted C 6 -60 aryl group; Halogen, alkyl, alkenyl, alkoxy, substituted or unsubstituted arylamine groups, substituted or unsubstituted aryl groups, substituted or unsubstituted arylalkyl groups, substituted or unsubstituted arylalkenyl groups, substituted or unsubstituted acetyl group of the heterocyclic group, a nitrile group, and a substituted or unsubstituted C 2 -40 with one or more substituents selected from the group consisting of an acetylene; Halogen, alkyl, alkenyl, alkoxy, substituted or unsubstituted arylamine groups, substituted or unsubstituted aryl groups, substituted or unsubstituted arylalkyl groups, substituted or unsubstituted arylalkenyl groups, substituted or unsubstituted C 3 -60 hetero ring group which is unsubstituted or substituted with one or more substituents selected from the group consisting of a hetero ring group, a nitrile group and an acetylene group and has O, N, S or P as a hetero atom; An amine group substituted with one or more substituents selected from the group consisting of an alkyl group, an alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group; An fluorenyl group substituted with one or more substituents selected from the group consisting of an alkyl group, an alkenyl group substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group; Bisspirofluorenyl groups; Halogen, alkyl, alkenyl, alkoxy, substituted or unsubstituted arylamine groups, substituted or unsubstituted aryl groups, substituted or unsubstituted arylalkyl groups, substituted or unsubstituted arylalkenyl groups, substituted or unsubstituted A carbazolyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a heterocyclic group, a nitrile group and an acetylene group; A nitrile group; Cyano; A nitro group; Amide group; An ester group; Selected from the group consisting of silane groups and germanium groups, where they can form condensed rings of aliphatic or hetero groups with adjacent groups.
상기 목적을 달성하기 위한 본 발명의 또 다른 측면은, 상기 화합물을 유기물층에 포함하는 유기전자소자를 제공한다.Another aspect of the present invention for achieving the above object, provides an organic electronic device comprising the compound in an organic material layer.
본 발명의 화합물은 유기 발광 소자에서 유기물층 물질, 특히 전자주입 물질 및/또는 전자수송 물질로 사용될 수 있으며, 이 화합물을 유기 발광 소자에 사용하는 경우 소자의 구동전압을 낮추고, 광효율을 향상시키며, 화합물의 열적 안정성에 의하여 소자의 수명 특성을 향상시킬 수 있다.The compound of the present invention may be used as an organic layer material, in particular, an electron injection material and / or an electron transporting material in an organic light emitting device, and when the compound is used in an organic light emitting device, the driving voltage of the device is lowered and the light efficiency is improved. Thermal stability of the device can improve the life characteristics of the device.
이하 본 발명을 더욱 구체적으로 설명한다.Hereinafter, the present invention will be described in more detail.
본 발명의 일 측면은 상기 화학식 1로 표시되는 화합물에 관한 것이다.One aspect of the present invention relates to a compound represented by Chemical Formula 1.
상기 화학식 1의 치환기를 상세히 설명하면 다음과 같다.When explaining the substituent of Formula 1 in detail.
상기 화학식 1의 알킬기 및 알콕시기의 탄소수는 특별히 한정되지 않으나 1-50인 것이 바람직하고, 1-40인 것이 더욱 바람직하다.Although carbon number of the alkyl group and the alkoxy group of the said Formula (1) is not specifically limited, It is preferable that it is 1-50, It is more preferable that it is 1-40.
또한, 상기 화학식 1의 알케닐기 및 아세틸기의 탄소수는 특별히 한정되지 않으나 2-50인 것이 바람직하고, 2-40인 것이 더욱 바람직하다.In addition, the carbon number of the alkenyl group and the acetyl group of the formula (1) is not particularly limited, but is preferably 2-50, more preferably 2-40.
또한, 상기 화학식 1의 아릴기의 탄소수는 특별히 한정되지 않으나 6-60인 것이 바람직하고, 6-50인 것이 더욱 바람직하다.In addition, although the carbon number of the aryl group of the said General formula (1) is not specifically limited, It is preferable that it is 6-60, It is more preferable that it is 6-50.
또한, 상기 화학식 1의 헤테로 고리기의 탄소수는 특별히 한정되지 않으나 3-60인 것이 바람직하고, 3-50인 것이 더욱 바람직하며, 이종원자로서 O, N, S 또는 P를 갖는 것이 바람직하다.In addition, the carbon number of the heterocyclic group of Formula 1 is not particularly limited, but is preferably 3-60, more preferably 3-50, and preferably has O, N, S or P as the hetero atom.
또한, 상기 화학식 1의 아릴알킬기의 탄소수는 특별히 한정되지 않으나 7-50인 것이 바람직하고, 7-40인 것이 더욱 바람직하다.In addition, although the carbon number of the arylalkyl group of the said Formula (1) is not specifically limited, It is preferable that it is 7-50, It is more preferable that it is 7-40.
또한, 상기 화학식 1의 아릴알케닐기의 탄소수는 특별히 한정되지 않으나 7-50인 것이 바람직하고, 7-40인 것이 더욱 바람직하다.In addition, although the carbon number of the aryl alkenyl group of the said Formula (1) is not specifically limited, It is preferable that it is 7-50, It is more preferable that it is 7-40.
또한, 상기 화학식 1의 아릴아민기의 탄소수는 특별히 한정되지 않으나 6-50인 것이 바람직하고, 6-40인 것이 더욱 바람직하다.In addition, the carbon number of the arylamine group of the formula (1) is not particularly limited, but is preferably 6-50, more preferably 6-40.
상기 화학식 1에서 특별한 설명이 없는 경우, "치환 또는 비치환된" 이라는 용어는 할로겐기, 알킬기, 알케닐기, 알콕시기, 아릴기, 아릴알킬기, 아릴알케닐기, 헤테로 고리기, 카바졸릴기, 플루오레닐기, 니트릴기 및 아세틸렌기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환되는 것이 바람직하나, 이들에만 한정되는 것은 아니다.Unless otherwise specified in Formula 1, the term "substituted or unsubstituted" is halogen, alkyl, alkenyl, alkoxy, aryl, arylalkyl, arylalkenyl, heterocyclic, carbazolyl, flu It is preferable to be substituted or unsubstituted with one or more substituents selected from the group consisting of an orenyl group, a nitrile group and an acetylene group, but is not limited thereto.
화합물 중에 포함되어 있는 알킬기의 길이는 화합물의 공액 길이에는 영향을 미치지 않고, 다만 부수적으로 화합물의 유기 발광 소자에의 적용 방법, 예컨대 진공증착법 또는 용액도포법의 적용에 영향을 미칠 수 있다.The length of the alkyl group contained in the compound does not affect the conjugated length of the compound, but may additionally affect the method of applying the compound to the organic light emitting device, such as vacuum deposition or solution coating.
상기 화학식 1의 치환기를 더 상세히 설명하면 다음과 같다.Hereinafter, the substituent of Formula 1 will be described in more detail.
상기 화학식 1에서 R1 내지 R10은 각각 독립적으로 수소; 중수소; C1 -40의 알킬기; C1 -40의 알콕시기; C1 -40의 알킬기 또는 C6 -60의 아릴기로 치환 또는 비치환된 C2 -40의 알케닐기; C2 -40의 아세틸기; C1 -40의 알킬기, 치환 또는 비치환된 C6 -60의 아릴아민기, 치환 또는 비치환된 C6 -60의 아릴기, 치환 또는 비치환된 C7 -50의 아릴알킬기, 치환 또는 비치환되고 이종원자로 O, N, S 또는 P를 갖는 C3 -40의 헤테로 고리기, 니트릴기, 실란기, 치환 또는 비치환된 플루오레닐기, 치환 또는 비치환된 비스스피로플루오레닐기 및 치환 또는 비치환된 카바졸릴기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환된 C6 -60의 아릴기; 이종원자로서 O, N, S 또는 P를 갖는 C3 -60의 헤테로 고리기, C7 -50의 아릴알킬기, C8 -40의 아릴알케닐기, C6 -50의 아릴아민기, C6 -12의 아릴기 또는 이종원자로서 O, N, S 또는 P를 갖는 C3 -60의 헤테로 고리기로 치환 또는 비치환된 카바졸릴기, 플루오레닐기 및 니트릴기로 이루어진 군에서 선택된 1개 이상의 치환기인 것이 바람직하다.In Formula 1, R 1 to R 10 are each independently hydrogen; heavy hydrogen; Alkyl group of C 1 -40; An alkoxy group of C 1 -40; An alkenyl group of C 1 -40 alkyl or C 6 -60 aryl groups substituted or unsubstituted C 2 -40 of the; Acetyl group of C 2 -40; Alkyl group of C 1 -40, substituted or unsubstituted C 6 -60 aryl amine group, a substituted or an aryl group, a substituted or unsubstituted C 6 -60 aryl group, a substituted or unsubstituted C 7 -50 the ring and ring heteroatom as O, N, S or a heterocyclic group of C 3 -40 having a P, a nitrile group, a silane group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spiro-bis fluorenyl group and a substituted or C 6 -60 aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of an unsubstituted carbazolyl group; Heteroatoms as O, N, S or a heterocyclic group of C 3 -60 having a P, an arylamine group of C 7 -50 arylalkyl group, C 8 -40 arylalkenyl group, C 6 -50 of, C 6 - At least one substituent selected from the group consisting of a carbazolyl group, a fluorenyl group, and a nitrile group, which is unsubstituted or substituted with a C 3 -60 heterocyclic group having O, N, S, or P as an aryl group or hetero atom of 12; desirable.
상기 화학식 1 에서, R1 내지 R10는 각각 독립적으로, 수소, 중수소, 메틸기, 에틸기, 페닐기, 비페닐기, 터페닐기, 스틸벤, 나프틸기, 안트라세닐기, 페나트렌기, 파이레닐기, 페릴레닐기, 플루오렌기, 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 피라다진기, 퀴놀리닐기, 이소퀴톨린기, 아크리딜기, 메톡시, 에톡시, 카바졸릴 및 하기 치환기로 이루어진 군에서 선택될 수 있다.In Formula 1, R 1 to R 10 are each independently hydrogen, deuterium, methyl group, ethyl group, phenyl group, biphenyl group, terphenyl group, stilbene, naphthyl group, anthracenyl group, phenanthrene group, pyrenyl group, pe Lilenyl group, fluorene group, thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, pyridazine group, quinolinyl group, isoquitoline group, ah It may be selected from the group consisting of a credyl group, methoxy, ethoxy, carbazolyl and the following substituents.
상기 화학식 1로 표시되는 화합물은 하기 화학식 1-1 내지 1-3 중 하나로 표시될 수 있다.The compound represented by Chemical Formula 1 may be represented by one of the following Chemical Formulas 1-1 to 1-3.
상기 화학식 1-1 내지 1-3에 있어서, R1 내지 R10은 각각 서로 같거나 상이하며, 청구항 1에서의 정의와 같고, X, Y 및 Z는 각각 독립적으로 In Chemical Formulas 1-1 to 1-3, R 1 to R 10 are the same as or different from each other, as defined in claim 1, and X, Y, and Z are each independently
할로겐기, 알킬기, 알케닐기, 알콕시기, 치환 또는 비치환된 아릴아민기, 치환 또는 비치환된 아릴기, 치환 또는 비치환된 아릴알킬기, 치환 또는 비치환된 아릴알케닐기, 치환 또는 비치환된 헤테로 고리기, 니트릴기, 실란기, 치환 또는 비 치환된 플루오레닐기, 치환 또는 비치환된 비스스피로플루오레닐기, 치환 또는 비치환된 카바졸릴기 및 아세틸렌기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환된 C6 -60의 아릴렌기; 할로겐기, 알킬기, 알케닐기, 알콕시기, 치환 또는 비치환된 아릴아민기, 치환 또는 비치환된 아릴기, 치환 또는 비치환된 아릴알킬기, 치환 또는 비치환된 아릴알케닐기, 치환 또는 비치환된 헤테로 고리기, 니트릴기 및 아세틸렌기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환되고 이종원소로 O, N, S 또는 P를 갖는 C3 -60의 2가 헤테로 고리기; 알킬기, 알케닐기 치환 또는 비치환된 아릴기, 치환 또는 비치환된 아릴알킬기, 치환 또는 비치환된 아릴알케닐기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환된 플루오레닐렌기; 비스스피로플루오레닐렌기; 및 할로겐기, 알킬기, 알케닐기, 알콕시기, 치환 또는 비치환된 아릴아민기, 치환 또는 비치환된 아릴기, 치환 또는 비치환된 아릴알킬기, 치환 또는 비치환된 아릴알케닐기, 치환 또는 비치환된 헤테로 고리기, 니트릴기 및 아세틸렌기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환된 카바졸릴렌기로 이루어진 군에서 선택된다.Halogen, alkyl, alkenyl, alkoxy, substituted or unsubstituted arylamine groups, substituted or unsubstituted aryl groups, substituted or unsubstituted arylalkyl groups, substituted or unsubstituted arylalkenyl groups, substituted or unsubstituted At least one substituent selected from the group consisting of a heterocyclic group, a nitrile group, a silane group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted bisspirofluorenyl group, a substituted or unsubstituted carbazolyl group, and an acetylene group A substituted or unsubstituted C 6 -60 arylene group; Halogen, alkyl, alkenyl, alkoxy, substituted or unsubstituted arylamine groups, substituted or unsubstituted aryl groups, substituted or unsubstituted arylalkyl groups, substituted or unsubstituted arylalkenyl groups, substituted or unsubstituted A C 3 -60 divalent hetero ring group unsubstituted or substituted with one or more substituents selected from the group consisting of a hetero ring group, a nitrile group and an acetylene group and having O, N, S or P as a hetero atom; A fluorenylene group substituted with at least one substituent selected from the group consisting of an alkyl group, an alkenyl group substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group; Bisspirofluorenylene group; And halogen, alkyl, alkenyl, alkoxy, substituted or unsubstituted arylamine groups, substituted or unsubstituted aryl groups, substituted or unsubstituted arylalkyl groups, substituted or unsubstituted arylalkenyl groups, substituted or unsubstituted Carbazolylene group unsubstituted or substituted with one or more substituents selected from the group consisting of a heterocyclic group, a nitrile group and an acetylene group.
상기 화학식 1로 표시되는 화합물은 바람직하게는 하기 구조식 1 내지 구조식 72 중 어느 하나로 표시될 수 있으나, 이에 한정되는 것은 아니다.The compound represented by Chemical Formula 1 may be preferably represented by any one of the following Chemical Formulas 1 to 72, but is not limited thereto.
상기 화학식 1로 표시되는 화합물의 일반적인 제조방법은 다음과 같다.A general method for preparing a compound represented by Chemical Formula 1 is as follows.
치환 또는 비치환된 2'-아미노아세토페논과 치환 또는 비치환된 페닐하이드라진으로 이민을 형성시킨 후, 고리화 반응을 통하여 아민이 치환된 인돌 유도체를 합성한다. 그리고 카보닐기를 포함하는 물질과 아민이 치환된 인돌 유도체로 이민 화 반응, 고리화 반응을 반복하여 상기 화학식 1로 표시되는 화합물을 합성할 수 있다.After imine is formed with substituted or unsubstituted 2'-aminoacetophenone and substituted or unsubstituted phenylhydrazine, an amine-substituted indole derivative is synthesized through a cyclization reaction. The compound represented by Chemical Formula 1 may be synthesized by repeating an imidization reaction and a cyclization reaction with an indole derivative substituted with an amine and a substance including a carbonyl group.
본 기술분야에서 통상의 지식을 가진 기술자라면 상기 일반적인 제조방법과 본 명세서의 실시예를 참고하여 상기 화학식 1로 표시되는 화합물을 용이하게 제조할 수 있다.Those skilled in the art can easily prepare the compound represented by Chemical Formula 1 with reference to the general preparation method and the examples of the present specification.
본 발명의 두 번째 측면은 제 1 전극, 제 2 전극, 및 상기 제 1 전극과 제 2 전극 사이에 배치된 1층 이상의 유기물층을 포함하는 유기전기소자로서, 상기 유기물층 중 1층 이상은 상기 화학식 1로 표시되는 화합물을 포함하는 것을 특징으로 하는, 유기 전기 소자에 관한 것이다.A second aspect of the present invention is an organic electric device comprising a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode, wherein at least one of the organic material layers is represented by Formula 1 It is related with the organic electric element characterized by including the compound represented by.
상기 화학식 1의 화합물들은 유기 발광 소자의 제조시 진공 증착법뿐만 아니라 용액 도포법에 의하여 유기물층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀코팅, 딥코팅, 잉크젯프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다. Compounds of Formula 1 may be formed as an organic layer by a solution coating method as well as vacuum deposition in the manufacture of the organic light emitting device. Here, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spray method, roll coating and the like, but is not limited thereto.
본 발명의 유기 전기 소자는 유기물층 중 1층 이상이 본 발명의 화합물, 즉 상기 화학식 1의 화합물들을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다. The organic electric device of the present invention may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of the present invention, that is, the compounds of Formula 1.
본 발명의 유기 전기 소자의 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다.The organic material layer of the organic electric device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
즉, 상기 유기 전기 소자에서, 상기 유기물층은 전자주입층 및 전자수송층을That is, in the organic electric device, the organic material layer is an electron injection layer and an electron transport layer
포함하고, 이 전자주입층 및 전자수송층이 상기 화학식 1로 표시되는 화합물 을 포함할 수 있다.And, the electron injection layer and the electron transport layer may include a compound represented by the formula (1).
또한, 상기 유기물층은 발광층을 포함하고, 이 발광층이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.In addition, the organic material layer may include a light emitting layer, and the light emitting layer may include a compound represented by Chemical Formula 1.
예컨대, 본 발명의 유기 전기 소자는 유기물층으로서 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등을 포함하는 구조를 가질 수 있다. 그러나, 유기 전기 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기물층을 포함할 수 있다.For example, the organic electric device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic material layer. However, the structure of the organic electric device is not limited thereto and may include a smaller number of organic material layers.
또한, 상기 유기 전기 소자는 유기발광소자, 유기인광소자, 유기태양전지, 유기감광체(OPC) 및 유기트랜지스터로 이루어진 군에서 선택될 수 있다.In addition, the organic electric device may be selected from the group consisting of an organic light emitting device, an organic phosphorescent device, an organic solar cell, an organic photoconductor (OPC) and an organic transistor.
또한, 상기 유기 전기 소자에서 상기 유기물층은 전자수송층을 포함하고, 이 전자수송층이 상기 화학식 1로 표시되는 화합물, 또는 이 화합물에 열 경화성 또는 광 경화성 작용기가 도입된 화합물을 포함할 수 있다. In addition, in the organic electric device, the organic material layer may include an electron transport layer, and the electron transport layer may include a compound represented by Chemical Formula 1, or a compound in which a heat curable or photocurable functional group is introduced into the compound.
또한, 사이 유기 전기 소자에서 상기 발광층이 상기 화학식 1로 표시되는 화합물, 또는 이 화합물에 열 경화성 또는 광 경화성 작용기가 도입된 화합물을 포함할 수 있다.In addition, in the organic electronic device, the light emitting layer may include a compound represented by Chemical Formula 1 or a compound in which a thermosetting or photocurable functional group is introduced into the compound.
본 발명의 유기 전기 소자는 예컨대 기판상에 제1 전극, 유기물층 및 제2 전극을 순차적으로 적층시킴으로써 제조할 수 있다. 이 때 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 PVD(Physical Vapor Deposition) 방법 등을 이용할 수 있으나, 이들 방법에만 한정되는 것은 아니다.The organic electric element of the present invention can be produced, for example, by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation may be used, but is not limited thereto.
상기 화학식 1로 표시되는 화합물들의 제조 방법 및 이들을 이용한 유기 발 광 소자의 제조는 이하의 제조예 및 실시예에서 구체적으로 설명한다. 그러나, 하기 제조예 및 실시예는 본 발명을 예시하기 위한 것이며, 본 발명의 범위가 이들에 의하여 한정되는 것은 아니다.The manufacturing method of the compounds represented by Chemical Formula 1 and the preparation of the organic light emitting device using the same will be described in detail in the following Preparation Examples and Examples. However, the following Preparation Examples and Examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.
<제조예 1> 구조식 1로 표시되는 화합물의 제조Preparation Example 1 Preparation of Compound Represented by Structural Formula 1
구조식 1A의 제조Preparation of Structural Formula 1A
2-브로모나프탈렌(34.8 g, 168 mmol)을 테트라하이드로퓨란(170 ml)에 녹인 후 -78 ℃로 온도를 낮추고 n-부틸리튬 2.5 M(67.3 mL, 168 mmol)을 천천히 첨가하 고, 이를 1 시간 동안 교반하였다. 이어서, 여기에 2-브로모안트라퀴논(21 g, 73.1 mmol)을 첨가하고 상온으로 온도를 서서히 올리면서 2시간 동안 교반하였다. 염화암모늄 수용액을 첨가하고 유기층을 분리한 후 황산마그네슘으로 건조 후 여과하였다. 여과액을 감압 건조하여 용매를 제거한 후 디에틸에테르로 재결정하여 구조식 1A(32.3 g, 82 %)를 얻었다.Dissolve 2-bromonaphthalene (34.8 g, 168 mmol) in tetrahydrofuran (170 ml), lower the temperature to -78 ° C and slowly add n-butyllithium 2.5 M (67.3 mL, 168 mmol), Stir for 1 hour. Subsequently, 2-bromoanthraquinone (21 g, 73.1 mmol) was added thereto and stirred for 2 hours while gradually raising the temperature to room temperature. An aqueous ammonium chloride solution was added, the organic layer was separated, dried over magnesium sulfate, and filtered. The filtrate was dried under a reduced pressure to remove the solvent and recrystallized with diethyl ether to obtain the Structural Formula 1A (32.3 g, 82%).
MS: [M+]+ = 543MS: [M +] + = 543
구조식 1B의 제조Preparation of Structural Formula 1B
구조식 1A(32.3g, 59.5 mmol), 요오드화칼륨(29.6 g, 178.4 mmol) 및 치아린산소다(38.0 g, 356.8 mmol)를 아세트산(150 mL)에 넣고 2 시간 동안 가열 교반하였다. 상온으로 온도를 낮춘 후, 생성된 침전물을 여과하고 물로 씻어준 후 건조하여 구조식 1B(25.5g, 84 %)를 얻었다. Structural Formula 1A (32.3 g, 59.5 mmol), potassium iodide (29.6 g, 178.4 mmol) and sodium thiorate (38.0 g, 356.8 mmol) were added to acetic acid (150 mL) and stirred for 2 hours. After lowering the temperature to room temperature, the resulting precipitate was filtered, washed with water and dried to obtain Structural Formula 1B (25.5g, 84%).
MS: [M+]+ = 509MS: [M +] + = 509
구조식 1C의 제조Preparation of Structural Formula 1C
구조식 1B(10 g, 19.6 mmol), 비스(피나콜라토)디보론(5.5 g, 21.8 mmol), 포타슘아세테이트(5.8 g, 58.8 mmol)를 디옥산(150 mL)에 녹인 후, 50℃로 온도를 올리고, Pd(dppf)Cl2(0.48 g, 0.6 mmol)를 첨가한 후 12시간 동안 가열 교반하였다. 반응 용액을 실온으로 냉각시킨 후, 증류수(100 mL)를 가하고 메틸렌 클로라이드(100 mL×3)로 추출하였다. 유기층을 농축시키고 에탄올로 재결정하여 구조식 1C(16.4 g, 92%)를 얻었다.Structural Formula 1B (10 g, 19.6 mmol), bis (pinacolato) diboron (5.5 g, 21.8 mmol), potassium acetate (5.8 g, 58.8 mmol) was dissolved in dioxane (150 mL), followed by temperature to 50 ° C. After adding Pd (dppf) Cl 2 (0.48 g, 0.6 mmol), the mixture was heated and stirred for 12 hours. After cooling the reaction solution to room temperature, distilled water (100 mL) was added and extracted with methylene chloride (100 mL x 3). The organic layer was concentrated and recrystallized with ethanol to obtain the Structural Formula 1C (16.4 g, 92%).
MS: [M+H]+ = 557MS: [M + H] + = 557
구조식 1D의 제조Preparation of Structural Formula 1D
2'-아미노아세토페논(9.6 mL, 80 mmol)과 페닐하이드라진(15g, 103.7 mmol)을 에탄올(100 mL)과 빙초산(30 mL)에 넣고 5시간 동안 가열 교반하였다. 상온으로 온도를 낮춘 후 생성된 고체를 여과하고 에탄올(30 mL)로 세척한 후 진공 건조시켜 구조식 1D(14 g, 수율 83 %)를 얻었다.2'-aminoacetophenone (9.6 mL, 80 mmol) and phenylhydrazine (15 g, 103.7 mmol) were added to ethanol (100 mL) and glacial acetic acid (30 mL), and the mixture was heated and stirred for 5 hours. After the temperature was lowered to room temperature, the resulting solid was filtered, washed with ethanol (30 mL), and dried in vacuo to obtain Structural Formula 1D (14 g, 83% yield).
MS: [M+H]+ = 226MS: [M + H] + = 226
구조식 1E의 제조Preparation of Structural Formula 1E
메탄설폰산(100 mL)에 오산화인(8.4 g, 58.7 mmol)을 넣고 80 ℃에서 오산화인이 완전히 녹을 때까지 교반하였다. 구조식 1D(6.3 g, 28 mmol)를 천천히 첨가한 후 90℃에서 3시간 동안 교반하고, 상온으로 온도를 내렸다. 반응액을 0 ℃의 수산화나트륨 수용액에 넣고 10분간 교반한 후 생성된 고체를 여과하였다. 증류수로 세척한 후 진공 건조하여 구조식 1E(4 g. 수율 69 %)를 얻었다.Phosphorous pentoxide (8.4 g, 58.7 mmol) was added to methanesulfonic acid (100 mL) and stirred at 80 ° C. until phosphorus pentoxide was completely dissolved. Structural Formula 1D (6.3 g, 28 mmol) was added slowly, stirred at 90 ° C. for 3 hours, and cooled to room temperature. The reaction solution was poured into an aqueous sodium hydroxide solution at 0 ° C., stirred for 10 minutes, and the resulting solid was filtered. After washing with distilled water and dried under vacuum to obtain the Structural Formula 1E (4 g. 69% yield).
MS: [M+H]+ = 209MS: [M + H] + = 209
구조식 1F의 제조Preparation of Structural Formula 1F
구조식 1E(4 g, 19.2 mmol)와 4-클로로베조일클로라이드(2.4 mL, 19.2 mmol)를 p-톨루엔술폰산(50 mL)에 넣고 5 시간 동안 가열교반하였다. 50 ℃로 온도를 낮춘 후 2,3-디클로로-5,6-디시아노-1,4-벤조퀴논(DDQ)(4.8 g, 21.1 mmol)를 천천히 첨가하였다. 2 시간 동안 가열교반한 후 상온으로 온도를 낮추고 탄산칼륨 수용액 을 천천히 첨가하였다. 30 분간 교반한 후 물층은 제거하고 생성된 고체를 여과하였다. 여과된 고체를 클로로포름에서 재결정하여 구조식 1F(5 g, 79 %)를 얻었다.Structural Formula 1E (4 g, 19.2 mmol) and 4-chlorobezoyl chloride (2.4 mL, 19.2 mmol) were added to p-toluenesulfonic acid (50 mL) and stirred for 5 hours by heating. After the temperature was lowered to 50 ° C., 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (4.8 g, 21.1 mmol) was slowly added. After stirring for 2 hours, the temperature was lowered to room temperature, and an aqueous solution of potassium carbonate was slowly added. After stirring for 30 minutes, the water layer was removed and the resulting solid was filtered off. The filtered solid was recrystallized in chloroform to obtain the structural formula 1F (5 g, 79%).
MS: [M+]+ = 328MS: [M +] + = 328
구조식 1의 제조 Preparation of Structural Formula 1
구조식 1C(8.5 g, 15.2 mmol)와 구조식 1F(5.0 g, 15.2 mmol)를 테트라하이드로퓨란(100 ml)에 가열하여 완전히 녹인 후, 2 M 탄산칼륨 수용액 100 ml를 첨가하고 Pd(PPh3)4(176 mg, 1.5 x 10-1 mmol)을 넣고 5 시간 동안 가열 교반하였다. 상온으로 온도를 낮춘 후 물층을 제거하고 생성된 고체를 여과하였다. 여과된 고체를 에틸아세테이트로 재결정하여 구조식 1(7.4 g, 수율 67 %)을 얻었다.Dissolve 1C (8.5 g, 15.2 mmol) and Structural Formula 1F (5.0 g, 15.2 mmol) in tetrahydrofuran (100 ml) to completely dissolve it, then add 100 ml of aqueous 2 M potassium carbonate solution and add Pd (PPh 3 ) 4 (176 mg, 1.5 × 10 −1 mmol) was added thereto, and the resulting mixture was heated and stirred for 5 hours. After lowering the temperature to room temperature, the water layer was removed and the resulting solid was filtered. The filtered solid was recrystallized with ethyl acetate to obtain the Structural Formula 1 (7.4 g, 67% yield).
MS: [M+H]+ = 723MS: [M + H] + = 723
<제조예 2> 구조식 8로 표시되는 화합물의 제조Preparation Example 2 Preparation of Compound Represented by
구조식 8A의 제조 Preparation of Structural Formula 8A
2-브로모-6-나프톨(10 g, 44.8 mmol)과 2-나프탈렌보론산(9.3 g, 53.8 mmol), 2 M 탄산칼륨 수용액(100 mL), Pd(PPh3)4(518 mg, 4.4 x 10-1 mmol)을 테트라하이드로퓨란(150 mL)에 넣고, 6 시간 동안 가열 교반하였다. 상온으로 온도를 낮춘 후 물층을 제거하고 생성된 고체를 여과하였다. 여과된 고체를 에탄올로 재결정하여 구조식 8A(9.8 g, 수율 81 %)를 얻었다.2-bromo-6-naphthol (10 g, 44.8 mmol) and 2-naphthaleneboronic acid (9.3 g, 53.8 mmol), aqueous 2 M potassium carbonate solution (100 mL), Pd (PPh 3 ) 4 (518 mg, 4.4 x 10 -1 mmol) was added to tetrahydrofuran (150 mL) and heated and stirred for 6 hours. After lowering the temperature to room temperature, the water layer was removed and the resulting solid was filtered. The filtered solid was recrystallized with ethanol to give the structural formula 8A (9.8 g, 81% yield).
MS: [M+H]+ = 271MS: [M + H] < + > = 271
구조식 8B의 제조Preparation of Structural Formula 8B
구조식 8A(9.8 g, 36.3 mmol)를 무수디클로로메탄(100 mL)에 녹인 후, 0 ℃로 온도를 낮추고 트리에틸아민(6.1 g, 43.6 mmol)을 첨가한 후 30분간 교반하였다. 트리플루오로메탄술폰산 무수물(7.3 mL, 43.6 mmol)을 천천히 첨가한 후 상온으로 온도를 올리고 1시간 동안 교반하였다. 0 ℃로 온도를 낮추고, 탄산수소나트륨 수용액(100 mL)을 천천히 첨가한 후 디클로로메탄으로 추출하고 물층은 제거하였다. 유기층을 농축시킨 후 n-헥산으로 재결정하여 구조식 8B(13.1 g. 수율 90 %)를 얻었다.After dissolving Structural Formula 8A (9.8 g, 36.3 mmol) in anhydrous dichloromethane (100 mL), the temperature was lowered to 0 ° C., triethylamine (6.1 g, 43.6 mmol) was added, followed by stirring for 30 minutes. Trifluoromethanesulfonic anhydride (7.3 mL, 43.6 mmol) was added slowly, and then the temperature was raised to room temperature and stirred for 1 hour. The temperature was lowered to 0 ° C., an aqueous sodium bicarbonate solution (100 mL) was added slowly, followed by extraction with dichloromethane, and the water layer was removed. The organic layer was concentrated and recrystallized with n-hexane to obtain the Structural Formula 8B (13.1 g. 90% yield).
MS: [M+H]+ = 403MS: [M + H] + = 403
구조식 8C의 제조Preparation of Structural Formula 8C
4-클로로벤조일클로라이드 대신 6-브로모-2-나프토일클로라이드를 사용한 것 을 제외하고, 구조식 1F의 제조방법과 동일한 방법으로 구조식 8C를 얻었다.Except for using 6-bromo-2-naphthoyl chloride instead of 4-chlorobenzoyl chloride, the formula 8C was obtained by the same method as the preparation method of formula 1F.
MS: [M+H]+ = 424MS: [M + H] + = 424
구조식 8D의 제조Preparation of Structural Formula 8D
구조식 1B 대신 구조식 8C를 사용한 것을 제외하고, 구조식 1C의 제조방법과 동일한 방법으로 구조식 8D를 얻었다.A structural formula 8D was obtained by the same method as the preparation method of structural formula 1C, except that structural formula 8C was used instead of structural formula 1B.
MS: [M+H]+ = 471MS: [M + H] + = 471
구조식 8의 제조Preparation of
2-브로모-6-나프톨 대신 구조식 8B, 2-나프탈렌보론산 대신 구조식 8D를 사용한 것을 제외하고, 구조식 8A의 제조방법과 동일한 방법으로 구조식 8을 얻었다.
MS: [M+]+ = 597MS: [M +] + = 597
<제조예 3> 구조식 11로 표시되는 화합물의 제조Preparation Example 3 Preparation of Compound Represented by Structural Formula 11
구조식 11A의 제조Preparation of Structural Formula 11A
2-브로모티오펜(10 g, 61.3 mmol)과 페닐보론산(9.0 g, 73.6 mmol)을 테트라하이드로퓨란(150 mL)에 녹인 후, 2M 탄산칼륨 수용액(100 mL)을 첨가한다. 50 ℃로 온도를 올린 후 Pd(PPh3)4(708 mg, 6.1x10-1 mmol)을 첨가하고 65 ℃로 승온하여 4시간 동안 교반한다. 상온으로 온도를 낮춘 후 물 층은 제거하고, 유기층의 용매를 감압증류하여 완전히 제거한 후 상온에서 헥산을 넣고 10분간 교반한다. 생성된 침전물은 여과하여 버리고, 여과액을 -10 ℃로 온도를 낮춘 후 1시간 동안 천천히 교반한다. 생성된 침전물을 여과한 후 상온에서 진공 건조하여 구조식 11A(9.1 g, 수율 93 %)를 얻었다.2-bromothiophene (10 g, 61.3 mmol) and phenylboronic acid (9.0 g, 73.6 mmol) are dissolved in tetrahydrofuran (150 mL), and then 2M aqueous potassium carbonate solution (100 mL) is added. After raising the temperature to 50 ℃ Pd (PPh 3 ) 4 (708 mg, 6.1x10 -1 mmol) is added, the temperature is raised to 65 ℃ and stirred for 4 hours. After the temperature was lowered to room temperature, the water layer was removed, the solvent of the organic layer was distilled off under reduced pressure to completely remove the hexane, and the mixture was stirred at room temperature for 10 minutes. The resulting precipitate is filtered off, and the filtrate is lowered to -10 ° C and stirred slowly for 1 hour. The resulting precipitate was filtered and dried in vacuo at room temperature to obtain Structural Formula 11A (9.1 g, yield 93%).
MS: [M+H]+ = 161MS: [M + H] + = 161
구조식 11B의 제조Preparation of Structural Formula 11B
구조식 11A(9.1 g, 56.8 mmol)를 클로로포름(100 mL)에 완전히 녹인 후 N-브로모숙신이미드(11.1 g, 62.5 mmol)를 천천히 첨가한 후 30분간 상온에서 교반하였다. 감압증류하여 용매를 완전히 제거한 후 0 ℃에서 에탄올을 넣고 20분간 교반하였다. 생성된 침전물을 여과하여 상온에서 진공 건조하여 구조식 11B(13.3 g, 수율 98 %)를 얻었다.Structural Formula 11A (9.1 g, 56.8 mmol) was completely dissolved in chloroform (100 mL), and N-bromosuccinimide (11.1 g, 62.5 mmol) was added slowly, followed by stirring at room temperature for 30 minutes. After distillation under reduced pressure to completely remove the solvent, ethanol was added at 0 ° C. and stirred for 20 minutes. The resulting precipitate was filtered and dried in vacuo at room temperature to obtain Structural Formula 11B (13.3 g, yield 98%).
MS: [M+]+ = 239MS: [M +] + = 239
구조식 11C의 제조Preparation of Structural Formula 11C
구조식 11B(13.3 g, 55.6 mmol)를 무수테트라하이드로퓨란 200 ml에 녹이고 -78 ℃로 냉각시킨 후, 2.5 M n-부틸리튬(24.5 mL, 61.2 mmol)을 천천히 첨가한 후 1시간 동안 교반하였다. 이 반응액에 트리메틸보레이트(9.4 mL, 83.4 mmol)를 첨가한 후 30 분간 교반하고 6N HCl 50 ml를 첨가한 후 온도를 상온으로 올려서 1 시간동안 교반하였다. 유기층을 추출하고 농축한 후, n-헥산으로 재결정하여 구조식 11C(10.0 g, 수율 88 %)를 얻었다.Structural Formula 11B (13.3 g, 55.6 mmol) was dissolved in 200 ml of anhydrous tetrahydrofuran, cooled to −78 ° C., and 2.5 M n-butyllithium (24.5 mL, 61.2 mmol) was added slowly, followed by stirring for 1 hour. Trimethyl borate (9.4 mL, 83.4 mmol) was added to the reaction solution, followed by stirring for 30 minutes. After adding 50 ml of 6N HCl, the temperature was raised to room temperature and stirred for 1 hour. The organic layer was extracted and concentrated, and then recrystallized with n-hexane to obtain the Structural Formula 11C (10.0 g, 88% yield).
MS: [M+H]+ = 205MS: [M + H] + = 205
구조식 11D의 제조Preparation of Structural Formula 11D
2-브로모-6-나프톨 대신 3-브로모-1-요오도벤젠, 2-나프탈렌보론산 대신 구조식 11C를 사용한 것을 제외하고, 구조식 8A의 제조방법과 동일한 방법으로 구조식 11D를 얻었다.Structural Formula 11D was obtained by the same method as the preparation method of Structural Formula 8A, except that 3-Bromo-1-iodobenzene instead of 2-bromo-6-naphthol and Structural Formula 11C were used instead of 2-naphthaleneboronic acid.
MS: [M+]+ = 315MS: [M +] + = 315
구조식 11E의 제조Preparation of Structural Formula 11E
구조식 11B 대신 구조식 11D를 사용한 것을 제외하고, 구조식 11C의 제조방법과 동일한 방법으로 구조식 11E를 얻었다.Structural formula 11E was obtained by the same method as the preparation method of structural formula 11C, except that structural formula 11D was used instead of structural formula 11B.
MS: [M+H]+ = 281MS: [M + H] + = 281
구조식 11F의 제조Preparation of Structural Formula 11F
구조식 1F(10 g, 30.4 mmol)를 클로로포름(250 mL)에 완전히 녹인 후, 0 ℃로 온도를 낮추고 브롬(1.6 mL, 30.4 mmol)을 천천히 첨가하였다. 20분간 교반한 후 얼음물에 반응액을 천천히 붇고, 5분간 교반한 후 생성된 고체를 여과한 후 컬 럼 정제를 통하여 구조식 11F(7.8 g, 수율 63 %)를 얻었다.Structural Formula 1F (10 g, 30.4 mmol) was completely dissolved in chloroform (250 mL), and then cooled to 0 ° C. and bromine (1.6 mL, 30.4 mmol) was added slowly. After stirring for 20 minutes, the reaction solution was slowly immersed in ice water, and after stirring for 5 minutes, the resulting solid was filtered and Structural Formula 11F (7.8 g, Yield 63%) was obtained through column purification.
MS: [M+]+ = 407MS: [M +] + = 407
구조식 11G의 제조Preparation of Structural Formula 11G
2-브로모-6-나프톨 대신 구조식 11F, 2-나프탈렌보론산 대신 구조식 11E를 사용한 것을 제외하고, 구조식 8A의 제조방법과 동일한 방법으로 구조식 11G를 얻었다.Structural Formula 11G was obtained by the same method as the preparation method of Structural Formula 8A, except that Structural Formula 11F instead of 2-bromo-6-naphthol, and Structural Formula 11E instead of 2-naphthaleneboronic acid.
MS: [M+H]+ = 563MS: [M + H] + = 563
구조식 11H의 제조 Preparation of Structural Formula 11H
구조식 1B 대신 구조식 11G를 사용한 것을 제외하고, 구조식 1C의 제조방법과 동일한 방법으로 구조식 11H를 얻었다.Structural Formula 11H was obtained by the same method as the preparation method of Structural Formula 1C, except that Structural Formula 11G was used instead of Structural Formula 1B.
MS: [M+H]+ = 655MS: [M + H] + = 655
구조식 11I의 제조Preparation of Structural Formula 11I
2,4,6-트리클로로-1,3,5-트리아진(15 g, 81.3 mmol)을 무수 테트라하이드로퓨란(150 mL)에 녹인 후, -78 ℃로 온도를 낮추고 1 M 페닐 마그네슘 브로미드(162.6 mL, 162.6 mmol)를 천천히 첨가한 후 상온으로 온도를 서서히 올리면서 3 시간 동안 교반하였다. 1 N 염산 수용액(100 mL)를 첨가한 후 물층을 제거하고 유기층을 농축시킨 후, n-헥산으로 재결정하여 구조식 11I를 얻었다. 2,4,6-trichloro-1,3,5-triazine (15 g, 81.3 mmol) was dissolved in anhydrous tetrahydrofuran (150 mL), then the temperature was lowered to -78 ° C and 1 M phenyl magnesium bromide (162.6 mL, 162.6 mmol) was added slowly, followed by stirring for 3 hours while slowly raising the temperature to room temperature. After adding 1N aqueous hydrochloric acid solution (100 mL), the water layer was removed, the organic layer was concentrated, and recrystallized with n-hexane to obtain the Structural Formula 11I.
MS: [M+H]+ = 268MS: [M + H] + = 268
구조식 11의 제조Preparation of Structural Formula 11
구조식 1C 대신 구조식 11H, 구조식 1F 대신 구조식 11I를 사용한 것을 제외하고, 구조식 1의 제조방법과 동일한 방법으로 구조식 11을 얻었다.Structural formula 11 was obtained by the same method as the preparation method of structural formula 1, except that structural formula 11H and structural formula 11I instead of structural formula 1F were used instead of structural formula 1C.
MS: [M+H]+ = 760MS: [M + H] + = 760
<제조예 4> 구조식 12로 표시되는 화합물의 제조Preparation Example 4 Preparation of Compound Represented by Structural Formula 12
구조식 12A의 제조Preparation of Structural Formula 12A
2-브로모나프탈렌 대신 브로모벤젠을 사용한 것을 제외하고, 구조식 1A의 제조방법과 동일한 방법으로 구조식 12A를 얻었다.Structural formula 12A was obtained by the same method as the preparation method of structural formula 1A, except that bromobenzene was used instead of 2-bromonaphthalene.
MS: [M+]+ = 443MS: [M +] + = 443
구조식 12B의 제조Preparation of Structural Formula 12B
구조식 1A 대신 구조식 12A를 사용한 것을 제외하고, 구조식 1B의 제조방법과 동일한 방법으로 구조식 12B를 얻었다.Structural formula 12B was obtained by the same method as the preparation method of structural formula 1B, except that structural formula 12A was used instead of structural formula 1A.
MS: [M+]+ = 409MS: [M +] + = 409
구조식 12C의 제조Preparation of Structural Formula 12C
구조식 1B 대신 구조식 12B를 사용한 것을 제외하고, 구조식 1C의 제조방법과 동일한 방법으로 구조식 12C를 얻었다.Structural formula 12C was obtained by the same method as the preparation method of structural formula 1C, except that structural formula 12B was used instead of structural formula 1B.
MS: [M+H]+ = 457MS: [M + H] < + > = 457
구조식 12D의 제조Preparation of Structural Formula 12D
2-브로모-6-나프톨 대신 구조식 12C, 2-나프탈렌보론산 대신 페닐보론산을 사용한 것을 제외하고, 구조식 8A의 제조방법과 동일한 방법으로 구조식 12D를 얻었다.Structural formula 12D was obtained by the same method as the preparation method of structural formula 8A, except that phenylboronic acid was used instead of 2-bromo-6-naphthol and phenylboronic acid instead of 2-naphthaleneboronic acid.
MS: [M+H]+ = 405MS: [M + H] + = 405
구조식 12E의 제조 Preparation of Structural Formula 12E
구조식 1B 대신 구조식 12D를 사용한 것을 제외하고, 구조식 1C의 제조방법과 동일한 방법으로 구조식 12E를 얻었다.Structural formula 12E was obtained by the same method as the preparation method of structural formula 1C, except that structural formula 12D was used instead of structural formula 1B.
MS: [M+H]+ = 497MS: [M + H] + = 497
구조식 12F의 제조 Preparation of Structural Formula 12F
구조식 1C 대신 구조식 12E, 구조식 1F 대신 9-브로모안트라센을 사용한 것을 제외하고, 구조식 1 제조방법과 동일한 방법으로 구조식 12F를 얻었다.Structural formula 12F was obtained by the same method as the preparation method of Structural Formula 1, except that 9-bromoanthracene was used instead of Structural Formula 1C and Structural Formula 1F.
MS: [M+H]+ = 547MS: [M + H] < + > = 547
구조식 12G의 제조Preparation of Structural Formula 12G
구조식 12F(10 g, 18.3 mmol)을 클로로포름(150 mL)에 완전히 녹인 후 N-브로모숙신이미드(3.4 g, 19.2 mmol)를 천천히 첨가한 후 30분간 상온에서 교반한다. 증류수(100 mL)를 첨가한 후, 유기층을 추출하여 농축시키고, 에탄올로 재결정하여 구조식 12G(10 g, 수율 87 %)를 얻었다.Structural Formula 12F (10 g, 18.3 mmol) is completely dissolved in chloroform (150 mL), and N-bromosuccinimide (3.4 g, 19.2 mmol) is slowly added, followed by stirring at room temperature for 30 minutes. After adding distilled water (100 mL), the organic layer was extracted and concentrated, and recrystallized with ethanol to obtain the structural formula 12G (10 g, 87% yield).
MS: [M+]+ = 625MS: [M +] + = 625
구조식 12의 제조 Preparation of Structural Formula 12
구조식 1C 대신 구조식 12C, 구조식 1F 대신 구조식 12G를 사용한 것을 제외하고, 구조식 1의 제조방법과 동일한 방법으로 구조식 12를 얻었다.Structural formula 12 was obtained by the same method as the preparation method of structural formula 1, except that structural formula 12C and structural formula 12G instead of structural formula 1F were used instead of structural formula 1C.
MS: [M+H]+ = 875MS: [M + H] + = 875
<제조예 5> 구조식 22로 표시되는 화합물의 제조Preparation Example 5 Preparation of Compound Represented by Structural Formula 22
구조식 22의 제조Preparation of Structural Formula 22
구조식 12E(10 g, 20.1 mmol)와 2,7-디브로모-9,9-디페닐플루오렌(4.4 g, 9.2 mmol)을 테트라하이드로퓨란(150 ml)에 가열하여 완전히 녹인 후, 2 M 탄산칼륨 수용액 100 ml를 첨가하고 Pd(PPh3)4(213 mg, 1.8 x 10-1 mmol)을 넣고 12 시간 동안 가열 교반하였다. 상온으로 온도를 낮춘 후 물층을 제거하고 생성된 고체를 여과하였다. 여과된 고체를 에틸아세테이트로 재결정하여 구조식 22(7.1 g, 수율 73 %)를 얻었다.Structural Formula 12E (10 g, 20.1 mmol) and 2,7-dibromo-9,9-diphenylfluorene (4.4 g, 9.2 mmol) were heated in tetrahydrofuran (150 ml) to completely dissolve and then 2 M 100 ml of potassium carbonate solution was added thereto, Pd (PPh 3 ) 4 (213 mg, 1.8 × 10 −1 mmol) was added thereto, and the mixture was heated and stirred for 12 hours. After lowering the temperature to room temperature, the water layer was removed and the resulting solid was filtered. The filtered solid was recrystallized with ethyl acetate to obtain the Structural Formula 22 (7.1 g, 73% yield).
MS: [M+H]+ = 1055MS: [M + H] + = 1055
<제조예 6> 구조식 25로 표시되는 화합물의 제조Preparation Example 6 Preparation of Compound Represented by Structural Formula 25
구조식 25A의 제조Preparation of Structural Formula 25A
구조식 12F 대신 N-페닐카바졸을 사용한 것을 제외하고, 구조식 12G의 제조방법과 동일한 방법으로 구조식 25A를 얻었다.Structural formula 25A was obtained by the same method as the preparation method of structural formula 12G, except that N-phenylcarbazole was used instead of structural formula 12F.
MS: [M+]+ = 322MS: [M +] + = 322
구조식 25B의 제조Preparation of Structural Formula 25B
2-브로모-6-나프톨 대신 구조식 25A, 2-나프탈렌보론산 대신 페닐보론산을 사용한 것을 제외하고, 구조식 8A의 제조방법과 동일한 방법으로 구조식 25B를 얻었다.Structural formula 25B was obtained by the same method as the preparation method of structural formula 8A, except that phenylboronic acid was used instead of 2-bromo-6-naphthol and phenylboronic acid instead of 2-naphthaleneboronic acid.
MS: [M+H]+ = 320MS: [M + H] + = 320
구조식 25C의 제조Preparation of Structural Formula 25C
구조식 12F 대신 구조식 25B를 사용한 것을 제외하고, 구조식 12G의 제조방법과 동일한 방법으로 구조식 25C를 얻었다. Structural formula 25C was obtained by the same method as the preparation method of structural formula 12G, except that structural formula 25B was used instead of structural formula 12F.
MS: [M+]+ = 398MS: [M +] + = 398
구조식 25D의 제조Preparation of Structural Formula 25D
2-브로모-6-나프톨 대신 구조식 25C, 2-나프탈렌보론산 대신 4-클로로페닐보론산을 사용한 것을 제외하고, 구조식 8A의 제조방법과 동일한 방법으로 구조식 25D를 얻었다.Structural formula 25D was obtained by the same method as the preparation method of structural formula 8A, except that 4-chlorophenylboronic acid was used instead of 2-bromo-6-naphthol and 4-chlorophenylboronic acid instead of 2-naphthaleneboronic acid.
MS: [M+H]+ = 430MS: [M + H] + = 430
구조식 25의 제조Preparation of Structural Formula 25
구조식 1C 대신 구조식 12E, 구조식 1F 대신 구조식 25D를 사용한 것을 제외하고, 구조식 1의 제조방법과 동일한 방법으로 구조식 25를 얻었다.Structural formula 25 was obtained by the same method as the preparation method of structural formula 1, except that structural formula 12E and structural formula 25D instead of structural formula 1F were used instead of structural formula 1C.
MS: [M+H]+ = 764MS: [M + H] + = 764
<제조예 7> 구조식 29로 표시되는 화합물의 제조Preparation Example 7 Preparation of Compound Represented by Structural Formula 29
구조식 29A의 제조Preparation of Structural Formula 29A
4-클로로벤조일클로라이드 대신 벤조일클로라이드를 사용한 것을 제외하고, 구조식 1F의 제조방법과 동일한 방법으로 구조식 29A를 얻었다.Structural formula 29A was obtained by the same method as the preparation method of structural formula 1F, except that benzoyl chloride was used instead of 4-chlorobenzoyl chloride.
MS: [M+H]+ = 295MS: [M + H] + = 295
구조식 29B의 제조Preparation of Structural Formula 29B
구조식 29A(10 g, 34.0 mmol)를 클로로포름(250 mL)에 완전히 녹인 후, 0℃ 로 온도를 낮추고 브롬(3.6 mL, 71.3 mmol)을 천천히 첨가하였다. 30분간 교반한 후, 상온으로 온도를 올리고 2시간 동안 교반하였다. 얼음물에 반응액을 천천히 붇고, 5분간 교반한 후 생성된 고체를 여과하고 컬럼 정제를 통하여 구조식 29B(11.5 g, 수율 75 %)를 얻었다.Structural Formula 29A (10 g, 34.0 mmol) was completely dissolved in chloroform (250 mL), and then cooled to 0 ° C. and bromine (3.6 mL, 71.3 mmol) was added slowly. After stirring for 30 minutes, the temperature was raised to room temperature and stirred for 2 hours. The reaction solution was slowly immersed in iced water, stirred for 5 minutes, and the resulting solid was filtered and Structural Formula 29B (11.5 g, yield 75%) was obtained through column purification.
MS: [M+]+ = 452MS: [M +] + = 452
구조식 29C의 제조Preparation of Structural Formula 29C
2-브로모-6-나프톨 대신 9-브로모안트라센, 2-나프탈렌보론산 대신 페닐보론산을 사용한 것을 제외하고, 구조식 8A의 제조방법과 동일한 방법으로 구조식 29C를 얻었다.Structural formula 29C was obtained by the same method as the preparation method of structural formula 8A, except for using phenylboronic acid instead of 9-bromoanthracene and 2-naphthaleneboronic acid instead of 2-bromo-6-naphthol.
MS: [M+H]+ = 255MS: [M + H] + = 255
구조식 29D의 제조Preparation of Structural Formula 29D
구조식 12F 대신 구조식 29C를 사용한 것을 제외하고, 구조식 12G의 제조방법과 동일한 방법으로 구조식 29D를 얻었다.Structural formula 29D was obtained by the same method as the preparation method of structural formula 12G, except that structural formula 29C was used instead of structural formula 12F.
MS: [M+]+ = 333MS: [M +] + = 333
구조식 29E의 제조Preparation of Structural Formula 29E
2-브로모-6-나프톨 대신 구조식 29D, 2-나프탈렌보론산 대신 4-클로로페닐보론산을 사용한 것을 제외하고, 구조식 8A의 제조방법과 동일한 방법으로 구조식 29E를 얻었다.Structural formula 29E was obtained by the same method as the preparation method of structural formula 8A, except that 4-chlorophenylboronic acid was used instead of 2-bromo-6-naphthol and Structural Formula 29D instead of 2-naphthaleneboronic acid.
MS: [M+H]+ = 365MS: [M + H] + = 365
구조식 29F의 제조Preparation of Structural Formula 29F
구조식 1B 대신 구조식 29E를 사용한 것을 제외하고, 구조식 1C의 제조방법과 동일한 방법으로 구조식 29F를 얻었다.Structural formula 29F was obtained by the same method as the preparation method of structural formula 1C, except that structural formula 29E was used instead of structural formula 1B.
MS: [M+H]+ = 457MS: [M + H] < + > = 457
구조식 29의 제조Preparation of Structural Formula 29
구조식 12E 대신 구조식 29F, 2,7-디브로모-9,9-디페닐플루오렌 대신 구조식 29B를 사용한 것을 제외하고, 구조식 22의 제조방법과 동일한 방법으로 구조식 29을 얻었다.Structural formula 29 was obtained by the same method as the preparation method of structural formula 22, except that structural formula 29F instead of structural formula 12E and structural formula 29B instead of 2,7-dibromo-9,9-diphenylfluorene were used.
MS: [M+H]+ = 951MS: [M + H] + = 951
<제조예 8> 구조식 35로 표시되는 화합물의 제조Preparation Example 8 Preparation of Compound Represented by Structural Formula 35
구조식 35A의 제조Preparation of Structural Formula 35A
4-클로로벤조일클로라이드 대신 4-메틸벤조일클로라이드를 사용한 것을 제외하고, 구조식 1F의 제조방법과 동일한 방법으로 구조식 35A를 얻었다.Structural Formula 35A was obtained by the same method as the preparation method of Structural Formula 1F, except that 4-methylbenzoyl chloride was used instead of 4-chlorobenzoyl chloride.
MS: [M+H]+ = 309MS: [M + H] + = 309
구조식 35B의 제조Preparation of Structural Formula 35B
구조식 1F 대신 구조식 35A를 사용한 것을 제외하고, 구조식 11F의 제조방법과 동일한 방법으로 구조식 35B를 얻었다.Structural Formula 35B was obtained by the same method as the preparation method of Structural Formula 11F, except that Structural Formula 35A was used instead of Structural Formula 1F.
MS: [M+]+ = 387MS: [M +] + = 387
구조식 35C의 제조Preparation of Structural Formula 35C
2-브로모-6-나프톨 대신 구조식 35B를 사용한 것을 제외하고, 구조식 8A의 제조방법과 동일한 방법으로 구조식 35C를 얻었다.Structural Formula 35C was obtained by the same method as the preparation method of Structural Formula 8A, except that Structural Formula 35B was used instead of 2-bromo-6-naphthol.
MS: [M+H]+ = 435MS: [M + H] + = 435
구조식 35D의 제조Preparation of Structural Formula 35D
구조식 1F 대신 구조식 35C를 사용한 것을 제외하고, 구조식 11F의 제조방법과 동일한 방법으로 구조식 35D를 얻었다.Structural Formula 35D was obtained by the same method as the preparation method of Structural Formula 11F, except that Structural Formula 35C was used instead of Structural Formula 1F.
MS: [M+]+ = 513MS: [M +] + = 513
구조식 35E의 제조Preparation of Structural Formula 35E
구조식 1B 대신 구조식 8B를 사용한 것을 제외하고, 구조식 1C의 제조방법과 동일한 방법으로 구조식 35E를 얻었다.Structural Formula 35E was obtained by the same method as the preparation method of Structural Formula 1C, except that Structural Formula 8B was used instead of Structural Formula 1B.
MS: [M+H]+ = 381MS: [M + H] + = 381
구조식 35의 제조Preparation of Structural Formula 35
구조식 1C 대신 구조식 35E, 구조식 1F 대신 구조식 35D를 사용한 것을 제외하고, 구조식 1의 제조방법과 동일한 방법으로 구조식 35를 얻었다.Structural formula 35 was obtained by the same method as the preparation method of structural formula 1, except that structural formula 35E instead of structural formula 1C and structural formula 35D were used instead of structural formula 1F.
MS: [M+H]+ = 687MS: [M + H] + = 687
<제조예 9> 구조식 40으로 표시되는 화합물의 제조Preparation Example 9 Preparation of Compound Expressed by Structural Formula 40
구조식 40A의 제조Preparation of Structural Formula 40A
구조식 1F 대신 구조식 29A를 사용한 것을 제외하고, 구조식 11F의 제조방법 과 동일한 방법으로 구조식 40A를 얻었다.Structural formula 40A was obtained by the same method as the preparation method of structural formula 11F, except that structural formula 29A was used instead of structural formula 1F.
MS: [M+]+ = 407MS: [M +] + = 407
구조식 40B의 제조Preparation of Structural Formula 40B
2-브로모-6-나프톨 대신 구조식 40A, 2-나프탈렌보론산 대신 페닐보론산을 사용한 것을 제외하고, 구조식 8A의 제조방법과 동일한 방법으로 구조식 40B를 얻었다.Structural formula 40B was obtained by the same method as the preparation method of structural formula 8A, except that phenylboronic acid was used instead of 2-bromo-6-naphthol and phenylboronic acid instead of 2-naphthaleneboronic acid.
MS: [M+H]+ = 371MS: [M + H] < + > = 371
구조식 40C의 제조Preparation of Structural Formula 40C
구조식 1F 대신 구조식 40B를 사용한 것을 제외하고, 구조식 11F의 제조방법과 동일한 방법으로 구조식 40C를 얻었다.Structural formula 40C was obtained by the same method as the preparation method of structural formula 11F, except that structural formula 40B was used instead of structural formula 1F.
MS: [M+]+ = 449MS: [M +] + = 449
구조식 40D의 제조Preparation of Structural Formula 40D
2-브로모-6-나프톨 대신 9-브로모안트라센을 사용한 것을 제외하고, 구조식 8A의 제조방법과 동일한 방법으로 구조식 40D를 얻었다.Structural formula 40D was obtained by the same method as the preparation method of structural formula 8A, except that 9-bromoanthracene was used instead of 2-bromo-6-naphthol.
MS: [M+H]+ = 305MS: [M + H] + = 305
구조식 40E의 제조Preparation of Structural Formula 40E
구조식 12F 대신 구조식 40D를 사용한 것을 제외하고, 구조식 12G의 제조방법과 동일한 방법으로 구조식 40E를 얻었다. Structural Formula 40E was obtained by the same method as the preparation method of Structural Formula 12G, except that Structural Formula 40D was used instead of Structural Formula 12F.
MS: [M+]+ = 383MS: [M +] + = 383
구조식 40F의 제조Preparation of Structural Formula 40F
구조식 11B 대신 구조식 40E를 사용한 것을 제외하고, 구조식 11C의 제조방법과 동일한 방법으로 구조식 40F를 얻었다.Structural formula 40F was obtained by the same method as the preparation method of Structural Formula 11C, except that Structural Formula 40E was used instead of Structural Formula 11B.
MS: [M+H]+ = 349MS: [M + H] + = 349
구조식 40의 제조Preparation of Structural Formula 40
구조식 1C 대신 구조식 40F, 구조식 1F 대신 구조식 40C를 사용한 것을 제외하고, 구조식 1의 제조방법과 동일한 방법으로 구조식 40를 얻었다.Structural formula 40 was obtained by the same method as the manufacturing method of structural formula 1 except that structural formula 40F instead of structural formula 1C and structural formula 40C instead of structural formula 1F were used.
MS: [M+H]+ = 673MS: [M + H] + = 673
<제조예 10> 구조식 42으로 표시되는 화합물의 제조Preparation Example 10 Preparation of Compound Represented by Structural Formula 42
구조식 42A의 제조Preparation of Structural Formula 42A
4-클로로벤조일클로라이드 대신 3-클로로벤조일클로라이드를 사용한 것을 제외하고, 구조식 1F의 제조방법과 동일한 방법으로 구조식 42A를 얻었다.Structural Formula 42A was obtained by the same method as the preparation method of Structural Formula 1F, except that 3-chlorobenzoyl chloride was used instead of 4-chlorobenzoyl chloride.
MS: [M+H]+ = 329MS: [M + H] < + > = 329
구조식 42B의 제조Preparation of Structural Formula 42B
구조식 29A 대신 구조식 42A를 사용한 것을 제외하고, 구조식 29B의 제조방법과 동일한 방법으로 구조식 42B를 얻었다.Structural formula 42B was obtained by the same method as the preparation method of structural formula 29B, except that structural formula 42A was used instead of structural formula 29A.
MS: [M+]+ = 486MS: [M +] + = 486
구조식 42C의 제조Preparation of Structural Formula 42C
구조식 11B 대신 4-요오도비페닐을 사용한 것을 제외하고, 구조식 11C의 제조방법과 동일한 방법으로 구조식 42C를 얻었다.Structural formula 42C was obtained by the same method as the preparation method of structural formula 11C, except that 4-iodobiphenyl was used instead of structural formula 11B.
MS: [M+H]+ = 199MS: [M + H] + = 199
구조식 42D의 제조Preparation of Structural Formula 42D
구조식 12E 대신 구조식 42C, 2,7-디브로모-9,9-디페닐플루오렌 대신 구조식 42B를 사용한 것을 제외하고, 구조식 22의 제조방법과 동일한 방법으로 구조식 42D를 얻었다.Structural formula 42D was obtained by the same method as the preparation method of Structural Formula 22, except that Structural Formula 42B was used instead of Structural Formula 12E, instead of Structural Formula 42C, 2,7-dibromo-9,9-diphenylfluorene.
MS: [M+H]+ = 633MS: [M + H] + = 633
구조식 42E의 제조Preparation of Structural Formula 42E
구조식 1B 대신 구조식 11B를 사용한 것을 제외하고, 구조식 1C의 제조방법과 동일한 방법으로 구조식 42E를 얻었다.Structural formula 42E was obtained by the same method as the preparation method of structural formula 1C, except that structural formula 11B was used instead of structural formula 1B.
MS: [M+H]+ = 287MS: [M + H] + = 287
구조식 42의 제조Preparation of Structural Formula 42
구조식 1C 대신 구조식 42E, 구조식 1F 대신 구조식 42D를 사용한 것을 제외하고, 구조식 1과 제조방법과 동일한 방법으로 구조식 42를 얻었다.Structural formula 42 was obtained in the same manner as in formula 1 and the manufacturing method, except that Structural Formula 42E instead of Structural Formula 1C and Structural Formula 42D were used instead of Structural Formula 1F.
MS: [M+H]+ = 757MS: [M + H] < + > = 757
<제조예 11> 구조식 61로 표시되는 화합물의 제조Preparation Example 11 Preparation of Compound Represented by Structural Formula 61
구조식 61A의 제조Preparation of Structural Formula 61A
2-브로모-6-나프톨 대신 1-브로모파이렌, 2-나프탈렌보론산 대신 3-클로로페닐보론산을 사용한 것을 제외하고, 구조식 8A의 제조방법과 동일한 방법으로 구조식 61A를 얻었다.Structural formula 61A was obtained by the same method as the preparation method of Structural Formula 8A, except that 3-chlorophenylboronic acid was used instead of 1-bromopyrene and 2-naphthalene boronic acid instead of 2-bromo-6-naphthol.
MS: [M+H]+ = 313MS: [M + H] + = 313
구조식 61B의 제조Preparation of Structural Formula 61B
구조식 1B 대신 구조식 61A를 사용한 것을 제외하고, 구조식 1C의 제조방법과 동일한 방법으로 구조식 61B를 얻었다.Structural formula 61B was obtained by the same method as the preparation method of structural formula 1C, except that structural formula 61A was used instead of structural formula 1B.
MS: [M+H]+ = 405MS: [M + H] + = 405
구조식 61의 제조Preparation of Structural Formula 61
구조식 1C 대신 구조식 61B, 구조식 1F 대신 구조식 42A를 사용한 것을 제외하고, 구조식 1과 제조방법과 동일한 방법으로 구조식 61을 얻었다.Structural formula 61 was obtained in the same manner as in formula 1 and the manufacturing method, except that Structural Formula 61B instead of Structural Formula 1C, and Structural Formula 42A instead of Structural Formula 1F.
MS: [M+H]+ = 571MS: [M + H] + = 571
<제조예 12> 구조식 69로 표시되는 화합물의 제조Preparation Example 12 Preparation of Compound Represented by Structural Formula 69
구조식 69A의 제조Preparation of Structural Formula 69A
2-브로모-6-나프톨 대신 구조식 40E, 2-나프탈렌보론산 대신 4-클로로페닐보론산을 사용한 것을 제외하고, 구조식 8A의 제조방법과 동일한 방법으로 구조식 69A를 얻었다.Structural formula 69A was obtained by the same method as the preparation method of structural formula 8A, except that 4-chlorophenylboronic acid was used instead of 2-bromo-6-naphthol and 4-chlorophenylboronic acid instead of 2-naphthaleneboronic acid.
MS: [M+H]+ = 415MS: [M + H] + = 415
구조식 69B의 제조Preparation of Structural Formula 69B
구조식 1B 대신 구조식 69A를 사용한 것을 제외하고, 구조식 1C의 제조방법과 동일한 방법으로 구조식 69B를 얻었다.Structural formula 69B was obtained by the same method as the preparation method of structural formula 1C, except that structural formula 69A was used instead of structural formula 1B.
MS: [M+H]+ = 507MS: [M + H] + = 507
구조식 69의 제조 Preparation of Structural Formula 69
구조식 1C 대신 구조식 69B, 구조식 1F 대신 구조식 40C를 사용한 것을 제외하고, 구조식 1 제조방법과 동일한 방법으로 구조식 69를 얻었다.Structural formula 69 was obtained by the same method as the formula 1 except that Structural Formula 69B instead of Structural Formula 1C and Structural Formula 40C instead of Structural Formula 1F were used.
MS: [M+H]+ = 749MS: [M + H] + = 749
<실시예 1>≪ Example 1 >
ITO(인듐주석산화물)가 1000 Å 두께로 박막 코팅된 유리 기판(corning 7059 glass)을, 분산제를 녹인 증류수에 넣고 초음파로 세척하였다. 세제는 Fischer Co.의 제품을 사용하였으며, 증류수는 Millipore Co. 제품의 필터(Filter)로 2차 걸러진 증류수를 사용하였다. ITO를 30 분간 세척한 후, 증류수로 2회 반복하여 초음파 세척을 10 분간 진행하였다. 증류수 세척이 끝난 후 이소프로필알콜, 아세톤, 메탄올 용제 순서로 초음파 세척을 하고 건조시켰다.A glass substrate (corning 7059 glass) coated with a thin film of ITO (Indium Tin Oxide) at a thickness of 1000 Å was placed in distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. The detergent was a product of Fischer Co. The distilled water was supplied by Millipore Co. Distilled water, which was secondly filtered with a filter of the product, was used. After ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After the distilled water was washed, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol solvent, followed by drying.
이렇게 준비된 ITO 투명 전극 위에 헥사니트릴 헥사아자트리페닐렌(hexanitrile hexaazatriphenylene)를 500 Å의 두께로 열 진공 증착하여 정공주입층을 형성하였다. 그 위에 정공을 수송하는 물질인 NPB(400 Å)를 진공 증착한 후 발광층으로 호스트 H1과 도판트 D1 화합물을 300 Å의 두께로 진공 증착하였다. 그 다음에 위 제조예 1에서 합성한 구조식 1 화합물(200 Å)을 전자주입 및 수송층으로 순차적으로 열 진공 증착하였다. 상기 전자 수송층 위에 순차적으로 12 Å 두께의 리튬 플루오라이드(LiF)와 2000 Å 두께의 알루미늄을 증착하여 음극을 형성하여, 유기 발광 소자를 제조하였다.Hexanitrile hexaazatriphenylene was thermally vacuum deposited to a thickness of 500 kPa on the prepared ITO transparent electrode to form a hole injection layer. NPB (400 kPa), which is a material for transporting holes, was vacuum deposited thereon, and the host H1 and the dopant D1 compound were vacuum deposited to a thickness of 300 kPa as a light emitting layer. Then, the compound of formula 1 (200 μs) synthesized in Preparation Example 1 was thermally vacuum-deposited sequentially with an electron injection and transport layer. A 12 Å thick lithium fluoride (LiF) layer and a 2000 Å thick aluminum layer were successively deposited on the electron transport layer to form a cathode, thereby preparing an organic light emitting device.
상기 전자 수송층의 비교예로 E1을 사용하였다.E1 was used as a comparative example of the electron transport layer.
상기의 과정에서 유기물의 증착 속도는 1 Å/sec를 유지하였고, 리튬플루오라이드는 0.2 Å/sec, 알루미늄은 3~7 Å/sec의 증착 속도를 유지하였다.In the above process, the deposition rate of the organic material was maintained at 1 Å / sec, lithium fluoride was 0.2 Å / sec, and the aluminum was maintained at a deposition rate of 3-7 Å / sec.
<실시예 2><Example 2>
상기 실시예 1에서 전자 수송층으로 제조예 2에서 합성한 구조식 1 대신 구조식 8를 사용한 것을 제외하고는 동일하게 실험하였다.Except for using the
<실시예 3><Example 3>
상기 실시예 1에서 전자 수송층으로 제조예 3에서 합성한 구조식 1 대신 구조식 11을 사용한 것을 제외하고는 동일하게 실험하였다.Except for using the structural formula 11 synthesized in Preparation Example 3 as the electron transport layer in Example 1 and was the same experiment.
<실시예 4><Example 4>
상기 실시예 1에서 전자 수송층으로 제조예 4에서 합성한 구조식 1 대신 구 조식 12을 사용한 것을 제외하고는 동일하게 실험하였다.Except for using the old breakfast 12 instead of the structural formula 1 synthesized in Preparation Example 4 as the electron transport layer in Example 1 was the same experiment.
<실시예 5><Example 5>
상기 실시예 1에서 전자 수송층으로 제조예 5에서 합성한 구조식 1 대신 구조식 22을 사용한 것을 제외하고는 동일하게 실험하였다.Except for using the formula 22 instead of the formula 1 synthesized in Preparation Example 5 as the electron transport layer in Example 1 was the same experiment.
<실시예 6><Example 6>
상기 실시예 1에서 전자 수송층으로 제조예 6에서 합성한 구조식 1 대신 구조식 25을 사용한 것을 제외하고는 동일하게 실험하였다.Except for using the structural formula 25 synthesized in Preparation Example 6 as the electron transport layer in Example 1 and was the same experiment.
<실시예 7>≪ Example 7 >
상기 실시예 1에서 전자 수송층으로 제조예 7에서 합성한 구조식 1 대신 구조식 29을 사용한 것을 제외하고는 동일하게 실험하였다.Except for using the formula 29 instead of the formula 1 synthesized in Preparation Example 7 as the electron transport layer in Example 1 was the same experiment.
<실시예 8>≪ Example 8 >
상기 실시예 1에서 전자 수송층으로 제조예 8에서 합성한 구조식 1 대신 구조식 35을 사용한 것을 제외하고는 동일하게 실험하였다.Except for using the structural formula 35 synthesized in Preparation Example 8 as the electron transport layer in Example 1 was the same experiment.
<실시예 9>≪ Example 9 >
상기 실시예 1에서 전자 수송층으로 제조예 9에서 합성한 구조식 1 대신 구조식 40를 사용한 것을 제외하고는 동일하게 실험하였다.Except for using the structural formula 40 synthesized in Preparation Example 9 as the electron transport layer in Example 1 and was the same experiment.
<실시예 10>≪ Example 10 >
상기 실시예 1에서 전자 수송층으로 제조예 10에서 합성한 구조식 1 대신 구조식 42를 사용한 것을 제외하고는 동일하게 실험하였다.Except for using the formula 42 instead of the formula 1 synthesized in Preparation Example 10 as the electron transport layer in Example 1 was the same experiment.
<실시예 11><Example 11>
상기 실시예 1에서 전자 수송층으로 제조예 11에서 합성한 구조식 1 대신 구조식 61를 사용한 것을 제외하고는 동일하게 실험하였다.Except for using the structural formula 61 synthesized in Preparation Example 11 as the electron transport layer in Example 1 and was the same experiment.
<실시예 12>≪ Example 12 >
상기 실시예 1에서 전자 수송층으로 제조예 12에서 합성한 구조식 1 대신 구조식 69를 사용한 것을 제외하고는 동일하게 실험하였다.Except for using the structural formula 69 synthesized in Preparation Example 12 as the electron transport layer in Example 1 and was the same experiment.
<비교예 1>≪ Comparative Example 1 &
상기 실시예 1에서 전자 수송층으로 제조예에서 합성한 구조식 1 대신 E1을 사용한 것을 제외하고는 동일하게 실험하였다.Except for using E1 instead of the formula 1 synthesized in Preparation Example in Example 1 as the electron transport layer was the same experiment.
상기 실시예와 같이 각각의 화합물을 정공 수송층 물질로 사용하여 제조한 유기 발광 소자를 실험한 결과를 표 1에 나타내었다.Table 1 shows the results of an experiment of an organic light emitting device manufactured using each compound as a hole transporting layer material as in the above examples.
[표 1][Table 1]
본 발명에 따른 화학식의 화합물 유도체는 유기발광소자를 비롯한 유기전기소자에서 전자 주입, 전자 수송, 정공 주입 및 수송, 또는 발광 물질 역할을 할 수 있으며, 본 발명에 따른 소자는 효율, 구동전압, 안정성 면에서 우수한 특성을 나타낸다.The compound derivative of the formula according to the present invention may serve as electron injection, electron transport, hole injection and transport, or a light emitting material in an organic electric device including an organic light emitting device, and the device according to the present invention has efficiency, driving voltage, and stability. Excellent properties in terms of appearance.
도 1은 기판(1), 양극(2), 발광층(3), 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a
도 2는 기판(1), 양극(2), 정공주입층(5), 정공수송층(6), 발광층(7), 전자수송층(8) 및 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.2 shows an example of an organic light emitting device consisting of a substrate 1, an anode 2, a
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| KR20200068393A (en) | 2018-12-05 | 2020-06-15 | 솔브레인 주식회사 | Compound and organic light emitting device comprising the same |
| KR20200070891A (en) | 2018-12-10 | 2020-06-18 | 솔브레인 주식회사 | Heterocyclic compound and organic light emitting device comprising the same |
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