KR20130043459A - Organic metal compounds and organic light emitting diodes comprising the same - Google Patents
Organic metal compounds and organic light emitting diodes comprising the same Download PDFInfo
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- KR20130043459A KR20130043459A KR1020110107604A KR20110107604A KR20130043459A KR 20130043459 A KR20130043459 A KR 20130043459A KR 1020110107604 A KR1020110107604 A KR 1020110107604A KR 20110107604 A KR20110107604 A KR 20110107604A KR 20130043459 A KR20130043459 A KR 20130043459A
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- 150000002736 metal compounds Chemical class 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 200
- 239000000126 substance Substances 0.000 claims abstract description 105
- 238000002347 injection Methods 0.000 claims abstract description 26
- 239000007924 injection Substances 0.000 claims abstract description 26
- 230000000903 blocking effect Effects 0.000 claims abstract description 16
- 230000005525 hole transport Effects 0.000 claims abstract description 16
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 150000002902 organometallic compounds Chemical class 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000001769 aryl amino group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 3
- 125000005104 aryl silyl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 238000000151 deposition Methods 0.000 claims description 3
- 229910052805 deuterium Inorganic materials 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 238000005286 illumination Methods 0.000 claims 1
- 238000004020 luminiscence type Methods 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 description 165
- 238000003786 synthesis reaction Methods 0.000 description 165
- 238000006243 chemical reaction Methods 0.000 description 84
- 239000010410 layer Substances 0.000 description 74
- 239000000463 material Substances 0.000 description 41
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000011368 organic material Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- -1 metal complex compound Chemical class 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 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 4
- 238000004528 spin coating Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 125000006686 (C1-C24) alkyl group Chemical group 0.000 description 1
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-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
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 1
- UPFTWKGGLHJPJX-UHFFFAOYSA-N 1-N,2,4-triphenylbenzene-1,3-diamine Chemical group C1(=CC=CC=C1)NC1=C(C(=C(C=C1)C1=CC=CC=C1)N)C1=CC=CC=C1 UPFTWKGGLHJPJX-UHFFFAOYSA-N 0.000 description 1
- OIRHKGBNGGSCGS-UHFFFAOYSA-N 1-bromo-2-iodobenzene Chemical compound BrC1=CC=CC=C1I OIRHKGBNGGSCGS-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
- SRQOBNUBCLPPPH-UHFFFAOYSA-N 1-ethyl-4-phenylbenzene Chemical group C1=CC(CC)=CC=C1C1=CC=CC=C1 SRQOBNUBCLPPPH-UHFFFAOYSA-N 0.000 description 1
- NTYDMFCZXBCEJY-UHFFFAOYSA-N 1-methyl-2-phenylcyclohexa-2,4-dien-1-amine Chemical group CC1(N)CC=CC=C1C1=CC=CC=C1 NTYDMFCZXBCEJY-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- DSQMLISBVUTWJB-UHFFFAOYSA-N 2,6-diphenylaniline Chemical group NC1=C(C=2C=CC=CC=2)C=CC=C1C1=CC=CC=C1 DSQMLISBVUTWJB-UHFFFAOYSA-N 0.000 description 1
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 1
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
- RKVIAZWOECXCCM-UHFFFAOYSA-N 2-carbazol-9-yl-n,n-diphenylaniline Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 RKVIAZWOECXCCM-UHFFFAOYSA-N 0.000 description 1
- WONYVCKUEUULQN-UHFFFAOYSA-N 2-methyl-n-(2-methylphenyl)aniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1C WONYVCKUEUULQN-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical group CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 1
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical group C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 1
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- MQFYUZCANYLWEI-UHFFFAOYSA-N 4-methylnaphthalen-1-amine Chemical group C1=CC=C2C(C)=CC=C(N)C2=C1 MQFYUZCANYLWEI-UHFFFAOYSA-N 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- QXDWMAODKPOTKK-UHFFFAOYSA-N 9-methylanthracen-1-amine Chemical group C1=CC(N)=C2C(C)=C(C=CC=C3)C3=CC2=C1 QXDWMAODKPOTKK-UHFFFAOYSA-N 0.000 description 1
- ILEFZGNFDZBUEC-UHFFFAOYSA-N C(CCC)C(CCCP)(CCCC)CCCC Chemical compound C(CCC)C(CCCP)(CCCC)CCCC ILEFZGNFDZBUEC-UHFFFAOYSA-N 0.000 description 1
- KSSJBGNOJJETTC-UHFFFAOYSA-N COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC Chemical class COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC KSSJBGNOJJETTC-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910019015 Mg-Ag Inorganic materials 0.000 description 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical group C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- 206010041349 Somnolence Diseases 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 125000000304 alkynyl group Chemical group 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
- 150000001412 amines Chemical class 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- 125000005872 benzooxazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 238000002484 cyclic voltammetry Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 125000004431 deuterium atom Chemical group 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
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- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
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- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
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- Electroluminescent Light Sources (AREA)
Abstract
Description
본 발명은 유기금속 화합물 및 이를 포함하는 유기전계발광소자에 관한 것으로서, 보다 상세하게는 우수한 열적특성 및 발광효율을 가지는 유기금속 화합물 및 이를 포함하는 유기전계발광소자에 관한 것이다.The present invention relates to an organic metal compound and an organic electroluminescent device comprising the same, and more particularly, to an organic metal compound having excellent thermal characteristics and luminous efficiency and an organic electroluminescent device comprising the same.
최근 표시장치의 대형화에 따라 공간 점유가 작은 평면표시소자의 요구가 증대되고 있는데, 대표적인 평면표시소자인 액정 디스플레이는 기존의 CRT(cathode ray tube)에 비해 경량화가 가능하다는 장점은 있으나, 시야각(viewing angle)이 제한되고 배면 광(back light)이 반드시 필요하다는 등의 단점을 갖고 있다. 이에 반하여, 새로운 평면표시소자인 유기전계발광소자(organic light emitting diode, OLED)는 자기 발광 현상을 이용한 디스플레이로서, 시야각이 크고, 액정 디스플레이에 비해 경박, 단소해질 수 있으며, 빠른 응답 속도 등의 장점을 가지고 있으며, 최근에는 풀-컬러(full-color)디스플레이 또는 조명으로의 응용이 기대되고 있다.Recently, as the size of the display device increases, the demand for a flat display device having a small space is increasing. A liquid crystal display, which is a typical flat display device, has a merit of being lighter than a conventional cathode ray tube (CRT). The disadvantage is that the angle is limited and the back light is necessary. In contrast, organic light emitting diodes (OLEDs), which are new flat panel display devices, are displays using self-luminous phenomena, which have a large viewing angle, are thinner and shorter than liquid crystal displays, and have fast response speed In recent years, the application to full-color display or lighting is expected.
유기 발광 현상을 이용하는 유기전계발광소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기전계발광소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어질 수 있다. 이러한 유기전계발광소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. 이러한 유기전계발광소자는 자발광, 고휘도, 고효율, 낮은 구동전압, 넓은 시야각, 높은 콘트라스트, 고속 응답성 등의 특성을 갖는 것으로 알려져 있다.An organic light emitting display device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. In this case, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. When it falls back to the ground, it glows. Such an organic electroluminescent device is known to have properties such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.
유기전계발광소자에서 유기물층으로 사용되는 재료는 기능에 따라, 발광 재료와 전하수송 재료, 예컨대 정공주입 재료, 정공수송 재료, 전자수송 재료, 전자주입 재료 등으로 분류될 수 있다. 상기 발광 재료는 분자량에 따라 고분자형과 저분자형으로 분류될 수 있고, 발광 메커니즘에 따라 전자의 일중항 여기상태로부터 유래되는 형광 재료와 전자의 삼중항 여기상태로부터 유래되는 인광 재료로 분류될 수 있다. 또한, 발광 재료는 발광색에 따라 청색, 녹색, 적색 발광 재료와 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 재료로 구분될 수 있다.The material used as the organic material layer in the organic electroluminescent device may be classified into a light emitting material and a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function. The light emitting material may be classified into a polymer type and a low molecular type depending on the molecular weight and may be classified into a fluorescent material derived from singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons according to an emission mechanism . In addition, the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.
한편, 발광 재료로서 하나의 물질만 사용하는 경우 분자간 상호 작용에 의하여 최대 발광 파장이 장파장으로 이동하고 색순도가 떨어지거나 발광 감쇄 효과로 소자의 효율이 감소되는 문제가 발생하므로, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여 발광 재료로서 호스트-도판트 시스템을 사용할 수 있다.On the other hand, when only one material is used as the light emitting material, the maximum emission wavelength is shifted to a long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect. A host-dopant system can be used as the luminescent material to increase the luminous efficiency through.
그 원리는 발광층을 형성하는 호스트보다 에너지 대역 간극이 작은 도판트를 발광층에 소량 혼합하면, 발광층에서 발생한 엑시톤이 도판트로 수송되어 효율이 높은 빛을 내는 것이다. 이 때, 호스트의 파장이 도판트의 파장대로 이동하므로, 이용하는 도판트의 종류에 따라 원하는 파장의 빛을 얻을 수 있다.When the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with a small amount of the light emitting layer, the excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host shifts to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.
유기전계발광소자가 전술한 우수한 특징들을 충분히 발휘하기 위해서는 소자 내 유기물층을 이루는 물질, 예컨대 정공주입 물질, 정공수송 물질, 발광 물질, 전자수송 물질, 전자주입 물질 등이 안정하고 효율적인 재료에 의하여 뒷받침되는 것이 선행되어야 하나, 아직까지 안정하고 효율적인 유기전계발광소자용 유기물층 재료의 개발이 충분히 이루어지지 않은 상태이다. 따라서, 당 기술분야에서는 새로운 재료의 개발이 계속 요구되고 있는 실정이다.In order for the organic electroluminescent device to fully exhibit the above-mentioned excellent features, the organic layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc. is supported by a stable and efficient material Although this should be preceded, the development of a stable and efficient organic material layer for an organic light emitting device has not been made yet. Therefore, the development of new materials in the art continues to be required.
발광 재료에서 발광 원리를 살펴보면, 양쪽 전극에서부터 주입된 전자와 정공이 결합에 의해 엑시톤(여기자)을 형성하는데, 이때 일중항 여기자의 경우 형광, 삼중항 여기자의 경우 인광에 관여한다. 생성 확률이 75%인 삼중항 여기자를 사용하는 인광재료는 생성 확률이 25%인 일중항 여기자를 사용하는 형광재료보다 뛰어난 발광 효율을 보인다.Looking at the light emission principle in the light emitting material, electrons and holes injected from both electrodes form an exciton (exciton) by a combination, where singlet excitons are involved in fluorescence and triplet excitons are involved in phosphorescence. Phosphorescent materials using triplet excitons having a 75% generation probability show superior luminous efficiency than fluorescent materials using singlet excitons with a 25% generation probability.
유기전계발광소자에 적용될 수 있는 고효율 인광체들은 매우 제한적인데, 인광 발광이 용이한 분자구조로는 계간전이가 용이한 분자 구조로 원자번호가 큰 금속을 포함하는 금속 착체로서 Ir, Pt, Eu, Tb, Re, Rh, Os 등의 전이금속을 이용한 인광물질의 개발이 진행되고 있고, 리간드의 종류에 따라서 발광특성이 결정된다. 다만, 휘도가 낮고 물질의 안정성이 떨어져 실제 소자에 적용하기에는 한계가 있어 신규 발광물질에 대한 연구가 활발히 진행되고 있고, 인광 발광효율이 우수한 물질에 대한 개발이 요구되고 있는 실정이다.High efficiency phosphors that can be applied to organic electroluminescent devices are very limited. Molecular structures that can easily emit phosphorescence are metal complexes containing a large atomic number of metals with easy molecular transitions. These include Ir, Pt, Eu, and Tb. The development of phosphors using transition metals such as, Re, Rh, Os, etc. is progressing, and luminescence properties are determined according to the type of ligand. However, since the luminance is low and the stability of the material is low, there is a limit to apply it to an actual device. Therefore, research on new light emitting materials is being actively conducted, and the development of a material having excellent phosphorescence efficiency is required.
본 발명이 해결하고자 하는 첫 번째 기술적 과제는 열적특성 및 발광효율이 우수한 유기금속 화합물을 제공하는 것이다.The first technical problem to be solved by the present invention is to provide an organometallic compound having excellent thermal characteristics and luminous efficiency.
본 발명이 해결하고자 하는 두 번째 기술적 과제는 상기 유기금속 화합물을 포함하는 유기전계발광소자를 제공하는 것이다.The second technical problem to be solved by the present invention is to provide an organic light emitting device comprising the organometallic compound.
본 발명은 상기 첫 번째 기술적 과제를 달성하기 위하여, 하기 [화학식 1]로 표시되는 유기금속 화합물을 제공한다.The present invention provides an organometallic compound represented by the following [Formula 1] in order to achieve the first technical problem.
[화학식 1][Formula 1]
상기 [화학식 1]에서,In the above formula (1)
상기 복수의 R 및 복수의 Z는 각각 독립적으로 수소, 중수소, 시아노기, 할로겐, 히드록시기, 니트로기, 탄소수 1-40의 알킬기, 탄소수 1-40의 알콕시기, 탄소수 1-40의 알킬아미노기, 탄소수 6-40의 아릴아미노기, 탄소수 3-40의 헤테로아릴아미노기, 탄소수 1-40의 알킬실릴기, 탄소수 6-40의 아릴실릴기, 탄소수 6-40의 아릴기, 탄소수 3-40의 아릴옥시기, 탄소수 3-40의 헤테로아릴기, 게르마늄기, 인, 보론으로 이루어진 군으로부터 선택되고,The plurality of R and the plurality of Z are each independently hydrogen, deuterium, cyano group, halogen, hydroxy group, nitro group, alkyl group of 1-40 carbon atoms, alkoxy group of 1-40 carbon atoms, alkylamino group of 1-40 carbon atoms, carbon number 6-40 arylamino group, 3-40 heteroarylamino group, C1-40 alkylsilyl group, C6-40 arylsilyl group, C6-40 aryl group, C3-40 aryloxy group , A heteroaryl group having 3 to 40 carbon atoms, a germanium group, phosphorus and boron;
상기 A1 내지 A8은 각각 독립적으로 탄소수 6-40의 방향족 고리, 탄소수 3-40의 헤테로 고리이며,A1 to A8 are each independently an aromatic ring having 6 to 40 carbon atoms and a hetero ring having 3 to 40 carbon atoms,
상기 B는 탄소 및 질소, 실리콘원자이고,B is carbon, nitrogen, silicon atoms,
상기 D1 및 D2는 각각 독립적으로 화학결합, C, N, O, S 및 Si 중에서 선택되며,The D1 and D2 are each independently selected from chemical bonds, C, N, O, S and Si,
상기 복수의 X는 각각 독립적으로 C 또는 N이고, 상기 복수의 X 중 적어도 두 개 이상은 백금 금속에 배위하는 N을 포함하고,Each of the plurality of Xs is independently C or N, and at least two or more of the plurality of Xs include N coordinating to a platinum metal,
상기 복수의 G는 각각 독립적으로 화학결합, 탄소수 1-4의 알킬렌 또는 (R-Zi)n이 치환된 탄소수 1-4의 알킬렌이며,The plurality of Gs are each independently a chemical bond, alkylene having 1 to 4 carbon atoms or alkylene having 1 to 4 carbon atoms substituted with (R-Zi) n,
상기 n 및 i는 각각 독립적으로 1 내지 40의 정수이고, 상기 n 및 i가 2 이상인 경우 상기 복수의 R 및 복수의 Z는 각각 독립적으로 동일하거나 상이하고,N and i are each independently an integer of 1 to 40, when n and i are 2 or more, the plurality of R and a plurality of Z are each independently the same or different,
상기 e는 0 내지 2의 정수이며,E is an integer of 0 to 2,
상기 [화학식 1]에서 인접한 작용기는 서로 결합하여 포화 또는 불포화 고리 및 헤테로 원자를 갖는 포화 또는 불포화 고리를 형성할 수 있다.Adjacent functional groups in [Formula 1] may combine with each other to form a saturated or unsaturated ring having a saturated or unsaturated ring and a hetero atom.
본 발명의 일 실시예에 의하면, 상기 [화학식 1]은 보다 구체적으로 하기 [화학식 2] 내지 [화학식 17]로 표시되는 군으로부터 선택되는 어느 하나일 수 있다.According to an embodiment of the present invention, [Formula 1] may be any one selected from the group represented by [Formula 2] to [Formula 17] more specifically.
[화학식 2] [화학식 3] [화학식 4] [화학식 5][Formula 2] [Formula 3] [Formula 4] [Formula 5]
[화학식 6] [화학식 7] [화학식 8] [화학식 9][Formula 6] [Formula 7] [Formula 8] [Formula 9]
[화학식 10] [화학식 11] [화학식 12] [화학식 13][Formula 10] [Formula 11] [Formula 12] [Formula 13]
[화학식 14] [화학식 15] [화학식 16] [화학식 17][Formula 14] [Formula 15] [Formula 16] [Formula 17]
상기 [화학식 2] 내지 [화학식 17]에서, 상기 R, A1 내지 A8, B, D, X, Z, n 및 i는 상기 [화학식 1]의 정의와 동일하다.In [Formula 2] to [Formula 17], wherein R, A1 to A8, B, D, X, Z, n and i are the same as the definition of [Formula 1].
본 발명은 상기 두 번째 기술적 과제를 달성하기 위하여,The present invention to achieve the second technical problem,
애노드; 캐소드; 및 상기 애노드 및 캐소드 사이에 개재되며, 상기 [화학식 1]로 표시되는 유기금속 화합물을 포함하는 층을 구비한 유기전계발광소자를 제공한다.Anode; Cathode; And it is interposed between the anode and the cathode, and provides an organic electroluminescent device having a layer comprising an organometallic compound represented by the above [Formula 1].
본 발명에 따른 [화학식 1]로 표시되는 유기금속 화합물을 유기물층에 포함하는 유기전계발광소자는 열적 특성 및 발광 효율이 매우 우수하기 때문에 디스플레이 및 조명 등에 유용하게 사용될 수 있다.The organic electroluminescent device including the organometallic compound represented by [Formula 1] in the organic material layer according to the present invention may be usefully used for display and lighting because of its excellent thermal characteristics and luminous efficiency.
도 1은 본 발명의 일 구체예에 따른 유기전계발광소자의 개략도이다.
도 2는 본 발명의 일 실시예에 따른 [화학식 21]의 TGA 및 DSC을 표시한 그래프이다.
도 3은 본 발명의 일 실시예에 따른 [화학식 37]의 TGA 및 DSC을 표시한 그래프이다.
도 4는 본 발명의 일 실시예에 따른 [화학식 90]의 TGA 및 DSC을 표시한 그래프이다.
도 5는 본 발명의 일 실시예에 따른 [화학식 115]의 TGA 및 DSC을 표시한 그래프이다.
도 6은 본 발명의 일 실시예에 따른 [화학식 115]와 비교예 1(BTPIr)의 EL 스펙트럼을 표시한 그래프이다.1 is a schematic diagram of an organic light emitting display device according to an embodiment of the present invention.
Figure 2 is a graph showing the TGA and DSC of [Formula 21] according to an embodiment of the present invention.
Figure 3 is a graph showing the TGA and DSC of the formula 37 according to an embodiment of the present invention.
Figure 4 is a graph showing the TGA and DSC of the formula 90 according to an embodiment of the present invention.
5 is a graph showing TGA and DSC of Formula 115 according to an embodiment of the present invention.
6 is a graph showing EL spectra of [Formula 115] and Comparative Example 1 (BTPIr) according to an embodiment of the present invention.
이하, 본 발명을 더욱 상세하게 설명한다.Hereinafter, the present invention will be described in more detail.
본 발명에 따른 유기금속 화합물은 종래 금속 착제 화합물보다 인광발광효율을 개선시킨 것으로서, 상기 [화학식 1]로 표시되는 신규의 유기 금속 화합물이고, 보다 구체적으로는 상기 [화학식 2] 내지 [화학식 17]로 표시되는 화합물 중에서 선택되는 어느 하나인 것을 특징으로 한다.The organometallic compound according to the present invention is a novel organometallic compound represented by the above [Formula 1] as improved phosphorescence emission efficiency than the conventional metal complex compound, and more specifically the above [Formula 2] to [Formula 17] It is characterized in that it is any one selected from the compounds represented by.
본 발명에 따른 유기금속 화합물에 있어서, 상기 [화학식 1] 내지 [화학식 17]의 치환기들을 보다 구체적으로 설명하면 하기와 같으며, 상기 [화학식 1]에서 인접한 작용기는 서로 결합하여 서로 결합하여 포화 또는 불포화 고리 및 헤테로 원자를 갖는 포화 또는 불포화 고리를 형성할 수 있다.In the organometallic compound according to the present invention, the substituents of [Formula 1] to [Formula 17] will be described in more detail as follows, and adjacent functional groups in [Formula 1] are bonded to each other to be saturated or It is possible to form saturated or unsaturated rings having unsaturated rings and hetero atoms.
상기 알킬기의 구체적인 예로는 메틸기, 에틸기, 프로필기, 이소부틸기, sec-부틸기, tert-부틸기, 펜틸기, iso-아밀기, 헥실기, 헵틸기, 옥틸기, 스테아릴기, 트리클로로메틸기, 트리플루오르메틸기 등을 들 수 있으며, 상기 알킬기 중 하나 이상의 수소 원자는 중수소 원자, 할로겐 원자, 히드록시기, 니트로기, 시아노기, 트리플루오로메틸기, 실릴기(이 경우 "알킬실릴기"라 함), 치환 또는 비치환된 아미노기(-NH2, -NH(R), -N(R')(R''), 여기서 R, R' 및 R"은 각각 독립적으로 탄소수 1 내지 24의 알킬기임(이 경우 "알킬아미노기"라 함)), 아미디노기, 히드라진기, 히드라존기, 카르복실기, 술폰산기, 인산기, 탄소수 1 내지 24의 알킬기, 탄소수 1 내지 24의 할로겐화된 알킬기, 탄소수 2 내지 24의 알케닐기, 탄소수 2 내지 24의 알키닐기, 탄소수 1 내지 24의 헤테로알킬기, 탄소수 5 내지 24의 아릴기, 탄소수 6 내지 24의 아릴알킬기, 탄소수 3 내지 24의 헤테로아릴기 또는 탄소수 3 내지 24의 헤테로아릴알킬기로 치환될 수 있다.Specific examples of the alkyl group include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl, heptyl, octyl, stearyl and trichloro Methyl, trifluoromethyl, and the like, and at least one hydrogen atom of the alkyl group may be a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a trifluoromethyl group, or a silyl group (in this case, referred to as an "alkylsilyl group"). ), A substituted or unsubstituted amino group (-NH 2 , -NH (R), -N (R ') (R''), wherein R, R' and R "are each independently an alkyl group having 1 to 24 carbon atoms (In this case, "alkylamino group")), amidino group, hydrazine group, hydrazone group, carboxyl group, sulfonic acid group, phosphoric acid group, C1-C24 alkyl group, C1-C24 halogenated alkyl group, C2-C24 Alkenyl groups, alkynyl groups having 2 to 24 carbon atoms, heteroalkyl groups having 1 to 24 carbon atoms, It may be substituted with a heteroaryl group of a small number of 5 to 24 aryl group, C 6 -C 24 aryl group, a C 3 -C 24 heteroaryl group, or having a carbon number of 3 to 24.
상기 알콕시기의 구체적인 예로는 메톡시기, 에톡시기, 프로폭시기, 이소부틸옥시기, sec-부틸옥시기, 펜틸옥시기, iso-아밀옥시기, 헥실옥시기 등을 들 수 있으며, 상기 알킬기의 경우와 마찬가지의 치환기로 치환가능하다.Specific examples of the alkoxy group include methoxy group, ethoxy group, propoxy group, isobutyloxy group, sec-butyloxy group, pentyloxy group, iso-amyloxy group, hexyloxy group, and the like. Substituent with the same substituent as the case may be sufficient.
상기 아릴기의 구체적인 예로는 페닐기, 2-메틸페닐기, 3-메틸페닐기, 4-메틸페닐기, 4-에틸페닐기, o-비페닐기, m-비페닐기, p-비페닐기, 4-메틸비페닐기, 4-에틸비페닐기, o-터페닐기, m-터페닐기, p-터페닐기, 1-나프틸기, 2-나프틸기, 1-메틸나프틸기, 2-메틸나프틸기, 안트릴기, 페난트릴기, 피레닐기, 플루오레닐기, 테트라히드로나프틸기 등과 같은 방향족 그룹을 들 수 있으며, 상기 알킬기의 경우와 마찬가지의 치환기로 치환가능하다. 예를 들어, 아미노기로 치환되는 경우는 "아릴아미노기", 실릴기로 치환되는 경우는 "아릴실릴기", 옥시기로 치환되는 경우는 "아릴옥시기"라 한다.Specific examples of the aryl group include a phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-ethylphenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, 4-methylbiphenyl group, 4-ethylbiphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, 1-naphthyl group, 2-naphthyl group, 1-methylnaphthyl group, 2-methylnaphthyl group, anthryl group, phenanthryl group Aromatic groups, such as a pyrenyl group, a fluorenyl group, a tetrahydro naphthyl group, etc. are mentioned, It can substitute by the same substituent as the case of the said alkyl group. For example, when substituted with an amino group, it is called "arylamino group", when substituted with a silyl group, it is called "arylsilyl group", and when substituted with an oxy group, it is called "aryloxy group".
상기 헤테로아릴기의 구체적인 예로는 피리디닐기, 피리미디닐기, 트리아지닐기, 인돌리닐기, 퀴놀린닐기, 피롤리디닐기, 피페리디닐기, 모폴리디닐기, 피페라디닐기, 카바졸릴기, 옥사졸릴기, 옥사디아졸릴기, 벤조옥사졸릴기, 치아졸릴기, 치아디아졸릴기, 벤조치아졸릴기, 트리아졸릴기, 이미다졸릴기, 벤조이미다졸기 등이 있으며, 상기 헤테로아릴기 중 하나 이상의 수소 원자는 상기 알킬기의 경우와 동일한 치환기로 치환가능하다.Specific examples of the heteroaryl group include a pyridinyl group, a pyrimidinyl group, a triazinyl group, an indolinyl group, a quinolinyl group, a pyrrolidinyl group, a piperidinyl group, a morpholidinyl group, a piperadinyl group, a carbazolyl group, an oxa There are a sleepy group, an oxadiazolyl group, a benzooxazolyl group, a chiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a triazolyl group, an imidazolyl group, a benzoimidazole group, and one of the heteroaryl groups. The above hydrogen atoms can be substituted with the same substituents as in the alkyl group.
상기 아릴아미노기는 디페닐아민기, 페닐나프틸아민기, 페닐비페닐아민기, 나프틸비페닐아민기, 디나프틸아민기, 디비페닐아민기, 디안트라세닐아민기, 3-메틸-페닐아민기, 4-메틸-나프틸아민기, 2-메틸-비페닐아민기, 9-메틸-안트라세닐아민기, 디톨릴 아민기, 페닐 톨릴 아민기, 트리페닐아미노페닐 아민기, 페닐 비페닐아미노 페닐 아민기, 나프틸 페닐아미노페닐 비페닐아민기 등을 들 수있으나, 이에만 한정되는 것은 아니다.The arylamino group is a diphenylamine group, a phenylnaphthylamine group, a phenylbiphenylamine group, a naphthylbiphenylamine group, a dinaphthylamine group, a dibiphenylamine group, a dianthracenylamine group, and 3-methyl-phenylamine Group, 4-methyl-naphthylamine group, 2-methyl- biphenylamine group, 9-methyl- anthracenylamine group, ditolyl amine group, phenyl tolyl amine group, triphenylaminophenyl amine group, phenyl biphenylamino A phenyl amine group, a naphthyl phenylaminophenyl biphenylamine group, etc. are mentioned, but it is not limited to this.
본 발명의 범위가 이에 의하여 제한되는 것은 아니나, 상기 [화학식 1]로 표시되는 유기 금속화합물은 보다 구체적으로 하기 [화학식 18] 내지 [화학식 177]로 표시되는 군으로부터 선택되는 어느 하나일 수 있다.The scope of the present invention is not limited thereto, but the organometallic compound represented by the above [Formula 1] may be any one selected from the group represented by the following [Formula 18] to [Formula 177].
[화학식 18] [화학식 19] [화학식 20] [화학식 21][Formula 18] [Formula 19] [Formula 20] [Formula 21]
[화학식 22] [화학식 23] [화학식 24] [화학식 25][Formula 22] [Formula 23] [Formula 24] [Formula 25]
[화학식 26] [화학식 27] [화학식 28] [화학식 29][Formula 26] [Formula 27] [Formula 28] [Formula 29]
[화학식 30] [화학식 31] [화학식 32] [화학식 33][Formula 30] [Formula 31] [Formula 32] [Formula 33]
[화학식 34] [화학식 35] [화학식 36] [화학식 37][Formula 34] [Formula 35] [Formula 36] [Formula 37]
[화학식 38] [화학식 39] [화학식 40] [화학식 41][Formula 38] [Formula 39] [Formula 40] [Formula 41]
[화학식 42] [화학식 43] [화학식 44] [화학식 45][Formula 42] [Formula 43] [Formula 44] [Formula 45]
[화학식 46] [화학식 47] [화학식 48] [화학식 49][Formula 46] [Formula 47] [Formula 48] [Formula 49]
[화학식 50] [화학식 51] [화학식 52] [화학식 53][Formula 50] [Formula 51] [Formula 52] [Formula 53]
[화학식 54] [화학식 55] [화학식 56] [화학식 57][Formula 54] [Formula 55] [Formula 56] [Formula 57]
[화학식 58] [화학식 59] [화학식 60] [화학식 61][Formula 58] [Formula 59] [Formula 60] [Formula 61]
[화학식 62] [화학식 63] [화학식 64] [화학식 65][Formula 62] [Formula 63] [Formula 64] [Formula 65]
[화학식 66] [화학식 67] [화학식 68] [화학식 69][Formula 66] [Formula 67] [Formula 68] [Formula 69]
[화학식 70] [화학식 71] [화학식 72] [화학식 73][Formula 70] [Formula 71] [Formula 72] [Formula 73]
[화학식 74] [화학식 75] [화학식 76] [화학식 77][Formula 74] [Formula 75] [Formula 76] [Formula 77]
[화학식 78] [화학식 79] [화학식 80] [화학식 81][Formula 78] [Formula 79] [Formula 80] [Formula 81]
[화학식 82] [화학식 83] [화학식 84] [화학식 85][Formula 82] [Formula 83] [Formula 84] [Formula 85]
[화학식 86] [화학식 87] [화학식 88] [화학식 89][Formula 86] [Formula 87] [Formula 88] [Formula 89]
[화학식 90] [화학식 91] [화학식 92] [화학식 93][Formula 90] [Formula 91] [Formula 92] [Formula 93]
[화학식 94] [화학식 95] [화학식 96] [화학식 97][Formula 94] [Formula 95] [Formula 96] [Formula 97]
[화학식 98] [화학식 99] [화학식 100] [화학식 101][Formula 98] [Formula 99] [Formula 100] [Formula 101]
[화학식 102] [화학식 103] [화학식 104] [화학식 105][Formula 102] [Formula 103] [Formula 104] [Formula 105]
[화학식 106] [화학식 107] [화학식 108] [화학식 109][Formula 106] [Formula 107] [Formula 108] [Formula 109]
[화학식 110] [화학식 111] [화학식 112] [화학식 113][Formula 110] [Formula 111] [Formula 112] [Formula 113]
[화학식 114] [화학식 115] [화학식 116] [화학식 117][Formula 114] [Formula 115] [Formula 116] [Formula 117]
[화학식 118] [화학식 119] [화학식 120] [화학식 121][Formula 118] [Formula 119] [Formula 120] [Formula 121]
[화학식 122] [화학식 123] [화학식 124] [화학식 125][Formula 122] [Formula 123] [Formula 124] [Formula 125]
[화학식 126] [화학식 127] [화학식 128] [화학식 129][Formula 126] [Formula 127] [Formula 128] [Formula 129]
[화학식 130] [화학식 131] [화학식 132] [화학식 133][Formula 130] [Formula 131] [Formula 132] [Formula 133]
[화학식 134] [화학식 135] [화학식 136] [화학식 137][Formula 134] [Formula 135] [Formula 136] [Formula 137]
[화학식 138] [화학식 139] [화학식 140] [화학식 141][Formula 138] [Formula 139] [Formula 140] [Formula 141]
[화학식 142] [화학식 143] [화학식 144] [화학식 145][Formula 142] [Formula 143] [Formula 144] [Formula 145]
[화학식 146] [화학식 147] [화학식 148] [화학식 149][Formula 146] [Formula 147] [Formula 148] [Formula 149]
[화학식 150] [화학식 151] [화학식 152] [화학식 153][Formula 150] [Formula 151] [Formula 152] [Formula 153]
[화학식 154] [화학식 155] [화학식 156] [화학식 157][Formula 154] [Formula 155] [Formula 156] [Formula 157]
[화학식 158] [화학식 159] [화학식 160] [화학식 161][Formula 158] [Formula 159] [Formula 160] [Formula 161]
[화학식 162] [화학식 163] [화학식 164] [화학식 165][Formula 162] [Formula 163] [Formula 164] [Formula 165]
[화학식 166] [화학식 167] [화학식 168] [화학식 169][Formula 166] [Formula 167] [Formula 168] [Formula 169]
[화학식 170] [화학식 171] [화학식 172] [화학식 173][Formula 170] [Formula 171] [Formula 172] [Formula 173]
[화학식 174] [화학식 175] [화학식 176] [화학식 177][Formula 174] [Formula 175] [Formula 176] [Formula 177]
또한, 본 발명은 애노드, 캐소드 및 상기 애노드와 상기 캐소드 사이에 개재되며, 상기 [화학식 1]로 표시되는 유기금속 화합물을 포함하는 유기전계발광소자를 제공한다.In addition, the present invention provides an organic light emitting device comprising an anode, a cathode and an organic metal compound represented between the anode and the cathode, and represented by the above [Formula 1].
이 때, 상기 유기금속 화합물이 포함된 층은 상기 애노드 및 캐소드 사이의 발광층인 것이 바람직하며, 애노드 및 캐소드 사이에는 정공주입층, 정공수송층, 전자저지층, 정공저지층, 전자수송층 및 전자주입층으로 이루어진 군으로부터 선택된 하나 이상의 층을 더 포함할 수 있다.At this time, the layer containing the organometallic compound is preferably a light emitting layer between the anode and the cathode, and between the anode and the cathode hole injection layer, hole transport layer, electron blocking layer, hole blocking layer, electron transport layer and electron injection layer It may further include one or more layers selected from the group consisting of.
구체적인 예로서, 정공수송층(HTL, Hole Transport Layer)이 추가로 적층되어 있고, 상기 캐소드와 상기 유기발광층 사이에 전자수송층(ETL, Electron Transport Layer)이 추가로 적층되어 있는 것일 수 있는데, 상기 정공수송층은 애노드로부터 정공을 주입하기 쉽게 하기 위하여 적층되는 것으로서, 상기 정공수송층의 재료로는 이온화 포텐셜이 작은 전자공여성 분자가 사용되는데, 주로 트리페닐아민을 기본 골격으로 하는 디아민, 트리아민 또는 테트라아민 유도체가 많이 사용되고 있다.As a specific example, a hole transport layer (HTL) may be further stacked, and an electron transport layer (ETL) may be additionally stacked between the cathode and the organic light emitting layer. The silver is stacked to facilitate the injection of holes from the anode, and the electron transport molecule having a small ionization potential is used as the material of the hole transport layer. A diamine, triamine or tetraamine derivative mainly based on triphenylamine is used. It is used a lot.
본 발명에서도 상기 정공수송층의 재료로서 당업계에 통상적으로 사용되는 것인 한 특별히 제한되지 않으며, 예를 들어, N,N'-비스(3-메틸페닐)-N,N'-디페닐-[1,1-비페닐]-4,4'-디아민(TPD) 또는 N,N'-디(나프탈렌-1-일)-N,N'-디페닐벤지딘 (a-NPD) 등을 사용할 수 있다.In the present invention, the material for the hole transport layer is not particularly limited as long as it is commonly used in the art. For example, N, N'-bis (3-methylphenyl) -N, N'- , 1-biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine (a-NPD).
상기 정공수송층의 하부에는 정공주입층(HIL, Hole Injecting Layer)을 추가적으로 더 적층할 수 있는데, 상기 정공주입층 재료 역시 당업계에서 통상적으로 사용되는 것인 한 특별히 제한되지 않고 사용할 수 있으며, 예를 들어 CuPc(copperphthalocyanine) 또는 스타버스트형 아민류인 TCTA(4,4',4"-tri(N-carbazolyl)triphenyl-amine), m-MTDATA(4,4',4"-tris-(3-methylphenylphenyl amino)triphenylamine) 등을 사용할 수 있다.A hole injection layer (HIL) may be further stacked on the lower portion of the hole transport layer. The hole injection layer material may also be used without particular limitation as long as it is commonly used in the art. For example, CuPc (copperphthalocyanine) or starburst amines TCTA (4,4 ', 4 "-tri (N-carbazolyl) triphenyl-amine), m-MTDATA (4,4', 4" -tris- (3-methylphenylphenyl amino) triphenylamine) and the like can be used.
또한, 본 발명에 따른 유기전계발광소자에 사용되는 상기 전자수송층은 캐소드로부터 공급된 전자를 유기발광층으로 원활히 수송하고 상기 유기발광층에서 결합하지 못한 정공의 이동을 억제함으로써 발광층 내에서 재결합할 수 있는 기회를 증가시키는 역할을 한다.In addition, the electron transport layer used in the organic electroluminescent device according to the present invention can transport electrons supplied from the cathode smoothly to the organic luminescent layer and inhibit the movement of holes which are not bonded in the organic luminescent layer, .
상기 전자수송층 재료로는 당 기술분야에서 통상적으로 사용되는 것이면 특별히 제한되지 않고 사용할 수 있음은 물론이며, 예를 들어 옥사디아졸 유도체인 PBD, BMD, BND 또는 Alq3 등을 사용할 수 있다.The electron transport layer material may be used without particular limitation as long as it is commonly used in the art, and for example, oxadiazole derivatives such as PBD, BMD, BND or Alq 3 may be used.
한편, 상기 전자수송층의 상부에는 캐소드로부터의 전자 주입을 용이하게 해주어 궁극적으로 파워효율을 개선 시키는 기능을 수행하는 전자주입층(EIL, Electron Injecting Layer)을 더 적층시킬 수도 있는데, 상기 전자주입층 재료 역시 당 기술분야에서 통상적으로 사용되는 것이면 특별한 제한없이 사용할 수 있으며, 예를 들어, LiF, NaCl, CsF, Li2O, BaO 등의 물질을 이용할 수 있다.Meanwhile, an electron injection layer (EIL) may be further stacked on the electron transport layer to facilitate electron injection from the cathode and ultimately improve power efficiency. Also commonly used in the art may be used without particular limitation, for example, it may be used a material such as LiF, NaCl, CsF, Li 2 O, BaO.
본 발명에 따른 유기전계발광소자는 표시소자, 디스플레이 소자 및 단색 또는 백색 조명용 소자 등에 사용될 수 있다.The organic light emitting display device according to the present invention can be used for a display device, a display device and a monochrome or white lighting device.
도 1은 본 발명의 유기전계발광소자의 구조를 나타내는 단면도이다. 본 발명에 따른 유기전계발광소자는 애노드(20), 정공수송층(40), 유기발광층(50), 전자수송층(60) 및 캐소드(80)을 포함하며, 필요에 따라 정공주입층(30)과 전자주입층(70)을 더 포함할 수 있으며, 그 이외에도 1층 또는 2층의 중간층을 더 형성하는 것도 가능하며, 정공저지층 또는 전자저지층을 더 형성시킬 수도 있다.1 is a cross-sectional view showing the structure of an organic light emitting display device according to the present invention. The organic electroluminescent device according to the present invention includes an
도 1을 참조하여 본 발명의 유기전계발광소자 및 그 제조방법에 대하여 살펴보면 다음과 같다. 먼저 기판(10) 상부에 애노드 전극용 물질을 코팅하여 애노드(20)를 형성한다. 여기에서 기판(10)으로는 통상적인 유기 EL 소자에서 사용되는 기판을 사용하는데 투명성, 표면 평활성, 취급용이성 및 방수성이 우수한 유기 기판 또는 투명 플라스틱 기판이 바람직하다. 그리고, 애노드 전극용 물질로는 투명하고 전도성이 우수한 산화인듐주석(ITO), 산화인듐아연(IZO), 산화주석(SnO2), 산화아연(ZnO) 등을 사용한다.The organic electroluminescent device of the present invention and its manufacturing method will be described with reference to FIG. First, the
상기 애노드(20) 전극 상부에 정공 주입층 물질을 진공열 증착, 또는 스핀 코팅하여 정공주입층(30)을 형성한다. 그 다음으로 상기 정공주입층(30)의 상부에 정공수송층 물질을 진공 열증착 또는 스핀 코팅하여 정공수송층(40)을 형성한다.The
이어서, 상기 정공수송층(40)의 상부에 유기발광층(50)을 적층하고 상기 유기발광층(50)의 상부에 선택적으로 정공저지층(미도시)을 진공 증착 방법, 또는 스핀 코팅 방법으로서 박막을 형성할 수 있다. 상기 정공저지층은 정공이 유기발광층을 통과하여 캐소드로 유입되는 경우에는 소자의 수명과 효율이 감소되기 때문에 HOMO(Highest Occupied Molecular Orbital) 레벨이 매우 낮은 물질을 사용함으로써 이러한 문제를 방지하는 역할을 한다. 이 때, 사용되는 정공 저지 물질은 특별히 제한되지는 않으나 전자수송능력을 가지면서 발광 화합물보다 높은 이온화 포텐셜을 가져야 하며 대표적으로 BAlq, BCP, TPBI 등이 사용될 수 있다.Subsequently, the organic
이러한 정공저지층 위에 전자수송층(60)을 진공 증착 방법, 또는 스핀 코팅 방법을 통해 증착한 후에 전자주입층(70)을 형성하고 상기 전자주입층(70)의 상부에 캐소드 형성용 금속을 진공 열증착하여 캐소드(80) 전극을 형성함으로써 유기 EL 소자가 완성된다. 여기에서 캐소드 형성용 금속으로는 리튬(Li), 마그네슘(Mg), 알루미늄(Al), 알루미늄-리듐(Al-Li), 칼슘(Ca), 마그네슘-인듐(Mg-In), 마그네슘-은(Mg-Ag) 등을 사용할 수 있으며, 전면 발광 소자를 얻기 위해서는 ITO, IZO를 사용한 투과형 캐소드를 사용할 수 있다.After the
또한, 본 발명의 다른 일실시예에 의하면, 상기 정공주입층, 정공수송층, 전자저지층, 발광층, 정공저지층, 전자수송층 및 전자주입층으로부터 선택된 하나 이상의 층은 단분자 증착방식 또는 용액공정에 의하여 형성될 수 있으며, 본 발명에 따른 유기전계발광소자는 표시소자, 디스플레이 소자 및 단색 또는 백색 조명용 소자에 사용될 수 있다.
According to another embodiment of the present invention, at least one layer selected from the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer is a single molecule deposition method or a solution process The organic light emitting display device according to the present invention may be used in display devices, display devices, and monochrome or white lighting devices.
이하, 바람직한 실시예를 들어 본 발명을 더욱 상세하게 설명한다. 그러나 이들 실시예는 본 발명을 보다 구체적으로 설명하기 위한 것으로, 본 발명의 범위가 이에 의하여 제한되지 않는다는 것은 당업계의 통상의 지식을 가진 자에게 자명할 것이다.
Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. It will be apparent to those skilled in the art, however, that these examples are provided to further illustrate the present invention, and the scope of the present invention is not limited thereto.
<실시예><Examples>
<합성예 1> [화학식 18]로 표시되는 화합물의 제조Synthesis Example 1 Preparation of Compound Represented by Formula 18
(1) [화학식 1-a]로 표시되는 화합물의 합성(1) Synthesis of Compound Represented by Formula (1-a)
하기 [반응식 1]에 의하여 [화학식 1-a]로 표시되는 화합물을 합성하였다.A compound represented by the formula (1-a) was synthesized by the following reaction scheme (1).
[반응식 1][Reaction Scheme 1]
[화학식 1-a][Chemical Formula 1-a]
500 mL 둥근 바닥 플라스크에 다이페닐아민 30 g(0.177 mol), 탄산 칼륨 49 g(0.355 mol), 염화구리 3.5 g(0.035 mol), 2-브로모아이오도벤젠 75.2 g(0.266 mol)에 다이메틸설폭사이드 300 mL를 넣고 12 시간 환류시켰다. 반응 종료 후 상온으로 온도를 내리고 추출한 뒤 유기층을 감압 농축 후 헥산으로 재결정을 실시하고 건조하여 [화학식 1-a]로 표시되는 화합물을 48.1 g(83.7 %) 얻었다.
In a 500 mL round bottom flask, 30 g (0.177 mol) of diphenylamine, 49 g (0.355 mol) of potassium carbonate, 3.5 g (0.035 mol) of copper chloride, and 75.2 g (0.266 mol) of 2-bromoiodobenzene 300 mL of the side was added and refluxed for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, extracted, and the organic layer was concentrated under reduced pressure, recrystallized with hexane, and dried to obtain 48.1 g (83.7%) of the compound represented by [Formula 1-a].
(2) [화학식 1-b]로 표시되는 화합물의 합성(2) Synthesis of Compound Represented by Formula (1-b)
하기 [반응식 2]에 의하여 [화학식 1-b]로 표시되는 화합물을 합성하였다.[Chemical Formula 1-b] was synthesized by the following
[반응식 2][Reaction Scheme 2]
[화학식 1-b][Chemical Formula 1-b]
2 L 둥근 바닥 플라스크에 1-브로모-3-아이오도벤젠 100 g(0.35 mol)과 다이에틸에터 1000 mL를 넣고 질소상태하에서 30 분간 교반시키고 반응물의 온도를 -78도까지 냉각시켰다. 1.6 몰 노말 부틸리튬 220.93 mL(0.35 mol)을 천천히 적가하였다. 동일한 온도에서 1 시간 동안 교반 후 3-브로모페닐알데하이드 107.13 mL(0.50 mol)을 천천히 적가하였다. 실온으로 온도를 올리고 2 시간 동안 교반하였다. 반응 종료 후 2 몰 염산 수용액으로 반응을 종결시키고 추출한 뒤 유기층을 감압농축 후 헥산으로 재결정을 실시하고 건조하여 [화학식 1-b]로 표시되는 화합물을 86.9 g(71.9%) 얻었다.
100 g (0.35 mol) of 1-bromo-3-iodobenzene and 1000 mL of diethyl ether were added to a 2 L round bottom flask, and the mixture was stirred for 30 minutes under nitrogen, and the reaction temperature was cooled to -78 degrees. 220.93 mL (0.35 mol) of 1.6 mol normal butyllithium was slowly added dropwise. After stirring for 1 hour at the same temperature, 107.13 mL (0.50 mol) of 3-bromophenylaldehyde was slowly added dropwise. The temperature was raised to room temperature and stirred for 2 hours. After completion of the reaction, the reaction was terminated and extracted with a 2 mole hydrochloric acid aqueous solution, and then the organic layer was concentrated under reduced pressure, recrystallized with hexane and dried to give 86.9 g (71.9%) of the compound represented by [Formula 1-b].
(3) [화학식 1-c]로 표시되는 화합물의 합성(3) Synthesis of Compound Represented by Formula (1-c)
하기 [반응식 3]에 의하여 [화학식 1-c]로 표시되는 화합물을 합성하였다.The compound represented by the formula (1-c) was synthesized by the following reaction scheme [3].
[반응식 3]Scheme 3
[화학식 1-c][Chemical Formula 1-c]
5 L 둥근 바닥 플라스크에 [반응식 2]로부터 얻은 [화학식 1-b]로 표시되는 화합물 10 g(0.05 mol)에 메틸렌클로라이드 150 mL를 넣고 피리디늄 다이클로매이트 25.7 g을 메틸렌클로라이드 200 mL에 녹여 반응물에 첨가하였다. 상온에서 12 시간동안 교반하였다. 반응 종료 후 에탄올 900 mL를 넣고 교반한 뒤 여과하여 유기층을 감압 농축 후 건조하여 [화학식 1-c]로 표시되는 화합물을 7.6 g(76.8%)을 얻었다.
In a 5 L round bottom flask, 150 mL of methylene chloride was added to 10 g (0.05 mol) of the compound represented by [Formula 1-b] obtained from [Scheme 2], and 25.7 g of pyridinium dichloromite was dissolved in 200 mL of methylene chloride. Was added. Stirred at room temperature for 12 hours. After completion of the reaction, 900 mL of ethanol was added thereto, stirred, and filtered. The organic layer was concentrated under reduced pressure and dried to obtain 7.6 g (76.8%) of the compound represented by [Formula 1-c].
(4) [화학식 1-d]로 표시되는 화합물의 합성(4) Synthesis of a compound represented by the formula (1-d)
하기 [반응식 4]에 의하여 [화학식 1-d]로 표시되는 화합물을 합성하였다.[Chemical Formula 1-d] was synthesized by the following Reaction Scheme 4.
[반응식 4][Reaction Scheme 4]
[화학식 1-d][Formula 1-d]
500 mL 둥근 바닥 플라스크에 2-브로모피리딘 30 g(0.19 mol)과 테트라하이드로퓨란 250 mL를 넣고 질소상태하에서 30 분간 교반 시키고 반응물의 온도를 -78도까지 냉각시켰다. 1.6 몰 노말 부틸리튬 142.41 mL(0.23 mol)을 천천히 적가하였다. 동일한 온도에서 1 시간 동안 교반한 후 트리메틸보레이트 29.64 mL(0.27 mol)을 천천히 적가하였다. 실온으로 온도를 올리고 2 시간 동안 교반하였다. 반응 종료 후 2 몰 염산 수용액으로 반응을 종결시키고 추출한 뒤 유기층을 감압농축한 후 헥산으로 재결정을 실시하고 건조하여 [화학식 1-d]로 표시되는 화합물을 15.6 g(66.8%)을 얻었다.
30 g (0.19 mol) of 2-bromopyridine and 250 mL of tetrahydrofuran were added to a 500 mL round bottom flask, and the mixture was stirred under nitrogen for 30 minutes and the reaction temperature was cooled to -78 ° C. 142.41 mL (0.23 mol) of 1.6 mol normal butyllithium was slowly added dropwise. After stirring for 1 hour at the same temperature, 29.64 mL (0.27 mol) of trimethylborate was slowly added dropwise. The temperature was raised to room temperature and stirred for 2 hours. After completion of the reaction, the reaction was terminated and extracted with a 2 molar hydrochloric acid aqueous solution, the organic layer was concentrated under reduced pressure, recrystallized with hexane and dried to obtain 15.6 g (66.8%) of the compound represented by the formula (1-d).
(5) [화학식 1-e]로 표시되는 화합물의 합성(5) Synthesis of Compound Represented by Formula (1-e)
하기 [반응식 5]에 의하여 [화학식 1-e]로 표시되는 화합물을 합성하였다.[Chemical Formula 1-e] was synthesized by the following
[반응식 5]
[화학식 1-e][Formula 1-e]
1 L 둥근 바닥 플라스크에 마그네슘 2.6 g(0.11 mol), [반응식 1]로부터 얻은 [화학식 1-a]로 표시되는 화합물 21.3 g(0.066 mol)과 테트라하이드로퓨란 600 mL를 넣고 질소상태하에서 상온에서 1 시간 동안 교반시켰다. [반응식 3]으로부터 얻은 [화학식 1-c]로 표시되는 화합물 20.1 g(0.06 mol)를 빨리 반응물에 첨가한 후 2시간 동안 환류시켰다. 반응물을 상온으로 온도를 내리고 0.1 몰 염산 수용액을 첨가하고 추출한 뒤 유기층을 감압 농축한 후 헥산을 사용하여 컬럼크로마토그래피로 정제하고 1 L 둥근 바닥 플라스크에 아세트산 500 mL와 염산 5 mL를 6 시간동안 환류시켰다. 반응 종료 후 상온으로 온도를 내리고 결정을 여과시켰다. 메탄올로 재결정을 실시하고 건조하여 [화학식 1-e]로 표시되는 화합물을 25.4 g (68.1%) 얻었다.
Into a 1 L round bottom flask, 2.6 g (0.11 mol) of magnesium, 21.3 g (0.066 mol) of the compound represented by [Formula 1-a] obtained from [Scheme 1], and 600 mL of tetrahydrofuran were added. Stir for hours. 20.1 g (0.06 mol) of the compound represented by [Formula 1-c] obtained from [Scheme 3] was quickly added to the reaction and then refluxed for 2 hours. The reaction was cooled to room temperature, 0.1 molar hydrochloric acid solution was added and extracted, the organic layer was concentrated under reduced pressure, purified by column chromatography using hexane, and 500 mL of acetic acid and 5 mL of hydrochloric acid were refluxed for 6 hours in a 1 L round bottom flask. I was. After the reaction was completed, the temperature was lowered to room temperature, and the crystals were filtered. Recrystallization with methanol and drying gave 25.4 g (68.1%) of the compound represented by [Formula 1-e].
(6) [화학식 1-f]로 표시되는 화합물의 합성(6) Synthesis of Compound Represented by Formula 1-f
하기 [반응식 6]에 의하여 [화학식 1-f]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 1-f] by the following [Scheme 6] was synthesized.
[반응식 6][Reaction Scheme 6]
[화학식 1-f][Formula 1-f]
5 L 둥근 바닥 플라스크에 [반응식 5]로부터 얻은 [화학식 1-e]로 표시되는 화합물 25.4 g(0.39 mol)에 2-피리딘보론산 19.5 g(0.16 mol), 테트라키스(트리페닐포스핀)팔라듐(0) 3.86 g(3.3 mmol), 탄산칼륨 46.16 g(0.33 mol), 톨루엔 125 mL, 테트라하이드로퓨란 125 mL, 물 50 mL를 첨가한 후 12 시간 동안 환류시켰다. 반응 종료 후 상온으로 온도를 내리고 추출한 뒤 유기층을 감압 농축한 후 헥산을 사용하여 컬럼크로마토그래피로 분리하고 고체를 건조하여 [화학식 1-f]로 표시되는 화합물을 24.8 g(65.9%) 얻었다.
19.5 g (0.16 mol) of 2-pyridine boronic acid and tetrakis (triphenylphosphine) palladium in 25.4 g (0.39 mol) of the compound represented by [Formula 1-e] obtained from [Scheme 5] in a 5 L round bottom flask (0) 3.86 g (3.3 mmol), 46.16 g (0.33 mol) of potassium carbonate, 125 mL of toluene, 125 mL of tetrahydrofuran, and 50 mL of water were added and refluxed for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, extracted, and the organic layer was concentrated under reduced pressure, separated by column chromatography using hexane, and dried to obtain 24.8 g (65.9%) of the compound represented by [Formula 1-f].
(7) [화학식 18]로 표시되는 화합물의 합성(7) Synthesis of Compound Represented by Formula 18
하기 [반응식 7]에 의하여 [화학식 18]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 18] was synthesized by the following [Scheme 7].
[반응식 7][Reaction Scheme 7]
[화학식 18][Chemical Formula 18]
250 mL 둥근 바닥 플라스크에 [반응식 6]으로부터 얻은 [화학식 1-f]로 표시되는 화합물 13.8 g(0.01 mol)과 PtCl2(PhCN)2 11.6 g(0.04 mol)과 자이렌 160 mL를 넣고 24시간 환류시켰다. 반응 종료 후 상온으로 온도를 내리고 결정을 여과한 뒤 메탄올로 씻어주었다. 클로로포름으로 재결정을 실시하고 건조하여 [화학식 5]로 표시되는 화합물을 8.9 g(48%) 얻었다.Into a 250 mL round bottom flask, add 13.8 g (0.01 mol) of compound represented by [Formula 1-f] obtained from [Scheme 6], 11.6 g (0.04 mol) of PtCl 2 (PhCN) 2 , and 160 mL of xylene for 24 hours. It was refluxed. After the reaction was completed, the temperature was lowered to room temperature, and the crystals were filtered and washed with methanol. Recrystallization from chloroform and drying gave 8.9 g (48%) of the compound represented by [Formula 5].
MS : m/z Anal. Calcd 756.75 [M]+ Found: 756 [M]+; Anal. Calcd. C41H27N3 Pt: C, 65.07; H, 3.60; N, 5.55; Pt, 25.78. Found: C, 64.97; H, 3.78; N, 5.67; Pt, 24.88.
MS: m / z Anal. Calcd 756.75 [M] < + > Found: 756 [M] < + >; Anal. Calcd. C 41 H 27 N 3 Pt: C, 65.07; H, 3.60; N, 5.55; Pt, 25.78. Found: C, 64.97; H, 3.78; N, 5.67; Pt, 24.88.
<합성예 2 > [화학식 21]로 표시되는 화합물의 제조Synthesis Example 2 Preparation of Compound Represented by Formula 21
(1) [화학식 2-a]로 표시되는 화합물의 합성(1) Synthesis of Compound Represented by [Formula 2-a]
하기 [반응식 8]에 의하여 [화학식 2-a]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 2-a] was synthesized by the following [Scheme 8].
[반응식 8][Reaction Scheme 8]
[화학식 2-a][Chemical Formula 2-a]
상기 <합성예 1>의 [반응식 1]과 동일한 방법으로 합성하여 [화학식 2-a]로 표시되는 화합물을 20.9 g(수율 62.1%) 얻었다.
Synthesis was carried out in the same manner as in [Scheme 1] of <Synthesis Example 1>, to obtain 20.9 g (yield 62.1%) of the compound represented by [Formula 2-a].
(2) [화학식 2-b]로 표시되는 화합물의 합성(2) Synthesis of Compound Represented by [Formula 2-b]
하기 [반응식 9]에 의하여 [화학식 2-b]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 2-b] was synthesized by the following [Scheme 9].
[반응식 9]Scheme 9
[화학식 2-b][Formula 2-b]
상기 <합성예 1>의 [반응식 5]와 동일한 방법으로 합성하여 [화학식 2-b]로 표시되는 화합물을 19.8 g (수율 60.7%) 얻었다.
Synthesis was carried out in the same manner as in [Scheme 5] of <Synthesis Example 1>, to obtain 19.8 g (yield 60.7%) of the compound represented by [Formula 2-b].
(3) [화학식 2-c]로 표시되는 화합물의 합성(3) Synthesis of Compound Represented by [Formula 2-c]
하기 [반응식 10]에 의하여 [화학식 2-c]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 2-c] was synthesized by the following [Scheme 10].
[반응식 10][Reaction Scheme 10]
[화학식 2-c][Chemical Formula 2-c]
상기 <합성예 1>의 [반응식 6]과 동일한 방법으로 합성하여 [화학식 2-b]로 표시되는 화합물을 11.8 g (수율 63.9%) 얻었다.
Synthesis was carried out in the same manner as in [Scheme 6] of <Synthesis Example 1>, to obtain 11.8 g (yield 63.9%) of the compound represented by [Formula 2-b].
(4) [화학식 21]로 표시되는 화합물의 합성(4) Synthesis of Compound Represented by Formula 21
하기 [반응식 11]에 의하여 [화학식 21]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 21] was synthesized by the following [Scheme 11].
[반응식 11][Reaction Scheme 11]
[화학식 21][Chemical Formula 21]
상기 <합성예 1>의 [반응식 7]과 동일한 방법으로 합성하여 [화학식 2-a]로 표시되는 화합물을 20.9 g (수율 62.1%) 얻었다.Synthesis was carried out in the same manner as in [Scheme 7] of <Synthesis Example 1>, to obtain 20.9 g (yield 62.1%) of the compound represented by [Formula 2-a].
MS : m/z Anal. Calcd 812.25 [M]+ Found: 812 [M]+; Anal. Calcd. C45H35N3Pt: C, 66.49; H, 4.34; N, 5.17. Found: C, 66.71; H, 4.62; N, 5.01.
MS: m / z Anal. Calcd 812.25 [M] < + > Found: 812 [M] < + >; Anal. Calcd. C 45 H 35 N 3 Pt: C, 66.49; H, 4. 34; N, 5.17. Found: C, 66.71; H, 4.62; N, 5.01.
<합성예 3 > [화학식 30]으로 표시되는 화합물의 제조Synthesis Example 3 Preparation of Compound Represented by
(1) [화학식 3-a]로 표시되는 화합물의 합성(1) Synthesis of Compound Represented by [Formula 3-a]
하기 [반응식 12]에 의하여 [화학식 3-a]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 3-a] was synthesized by the following [Scheme 12].
[반응식 12][Reaction Scheme 12]
[화학식 3-a][Formula 3-a]
상기 <합성예 1>의 [반응식 6]과 동일한 방법으로 합성하여 [화학식 3-a]로 표시되는 화합물을 7.4 g (수율 70.6%) 얻었다.
Synthesis was carried out in the same manner as in [Scheme 6] of <Synthesis Example 1>, to obtain 7.4 g (yield 70.6%) of the compound represented by [Formula 3-a].
(2) [화학식 30]으로 표시되는 화합물의 합성(2) Synthesis of Compound Represented by
하기 [반응식 13]에 의하여 [화학식 30]으로 표시되는 화합물을 합성하였다.The compound represented by [Formula 30] was synthesized by the following [Scheme 13].
[반응식 13][Reaction Scheme 13]
[화학식 30](30)
상기 <합성예 1>의 [반응식 7]과 동일한 방법으로 합성하여 [화학식 2-a]로 표시되는 화합물을 4.1 g (수율 45.6%) 얻었다.Synthesis was carried out in the same manner as in [Scheme 7] of <Synthesis Example 1>, and 4.1 g (yield 45.6%) of the compound represented by [Formula 2-a] was obtained.
MS : m/z Anal. Calcd 848.23 [M]+ Found: 848 [M]+; Anal. Calcd. C45H33F2N3Pt: C, 63.67; H, 3.92; N, 4.95. Found: C, 63.27; H, 3.77; N, 5.01.
MS: m / z Anal. Calcd 848.23 [M] < + > Found: 848 [M] < + >; Anal. Calcd. C 45 H 33 F 2 N 3 Pt: C, 63.67; H, 3.92; N, 4.95. Found: C, 63.27; H, 3.77; N, 5.01.
<합성예 4 > [화학식 37]로 표시되는 화합물의 제조Synthesis Example 4 Preparation of Compound Represented by Chemical Formula 37
(1) [화학식 4-a]로 표시되는 화합물의 합성(1) Synthesis of Compound Represented by Formula 4-a
하기 [반응식 13]에 의하여 [화학식 4-a]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 4-a] was synthesized by the following [Scheme 13].
[반응식 13][Reaction Scheme 13]
[화학식 4-a][Chemical Formula 4-a]
상기 <합성예 1>의 [반응식 1]과 동일한 방법으로 합성하여 [화학식 4-a]로 표시되는 화합물을 15.0 g (수율 59.6%) 얻었다.
Synthesis was carried out in the same manner as in [Scheme 1] of <Synthesis Example 1>, to obtain 15.0 g (yield 59.6%) of the compound represented by [Formula 4-a].
(2) [화학식 4-b]로 표시되는 화합물의 합성(2) Synthesis of Compound Represented by Formula 4-b
하기 [반응식 14]에 의하여 [화학식 4-b]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 4-b] was synthesized by the following [Scheme 14].
[반응식 14][Reaction Scheme 14]
[화학식 4-b][Formula 4-b]
상기 <합성예 1>의 [반응식 5]와 동일한 방법으로 합성하여 [화학식 4-b]로 표시되는 화합물을 16.2 g (수율 66.1%) 얻었다
Synthesis was carried out in the same manner as in [Scheme 5] of <Synthesis Example 1> to obtain 16.2 g (yield 66.1%) of the compound represented by [Formula 4-b].
(3) [화학식 4-c]로 표시되는 화합물의 합성(3) Synthesis of Compound Represented by Formula 4-c
하기 [반응식 15]에 의하여 [화학식 4-c]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 4-c] was synthesized by the following [Scheme 15].
[반응식 15][Reaction Scheme 15]
[화학식 4-c][Chemical formula 4-c]
상기 <합성예 1>의 [반응식 6]과 동일한 방법으로 합성하여 [화학식 4-c]로 표시되는 화합물을 10.4 g (수율 65.7%) 얻었다
Synthesis was carried out in the same manner as in [Scheme 6] of <Synthesis Example 1> to obtain 10.4 g (yield 65.7%) of the compound represented by [Formula 4-c].
(4) [화학식 37]로 표시되는 화합물의 합성(4) Synthesis of Compound Represented by Formula 37
하기 [반응식 16]에 의하여 [화학식 37]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 37] was synthesized by the following [Scheme 16].
[반응식 16][Reaction Scheme 16]
[화학식 22][Formula 22]
상기 <합성예 1>의 [반응식 7]과 동일한 방법으로 합성하여 [화학식 37]로 표시되는 화합물을 11.8 g (수율 63.9%) 얻었다.Synthesis was carried out in the same manner as in [Scheme 7] of <Synthesis Example 1>, to obtain 11.8 g (yield 63.9%) of the compound represented by [Formula 37].
MS : m/z Anal. Calcd 814.26 [M]+ Found: 814 [M]+; Anal. Calcd. C45H37N3Pt: C, 66.33; H, 4.58; N, 5.16. Found: C, 66.12; H, 4.43; N, 5.24.
MS: m / z Anal. Calcd 814.26 [M] < + > Found: 814 [M] < + >; Anal. Calcd. C 45 H 37 N 3 Pt: C, 66.33; H, 4.58; N, 5.16. Found: C, 66.12; H, 4.43; N, 5.24.
<합성예 5 > [화학식 78]로 표시되는 화합물의 제조Synthesis Example 5 Preparation of Compound Represented by Formula 78
(1) [화학식 5-a]로 표시되는 화합물의 합성(1) Synthesis of a compound represented by the formula (5-a)
하기 [반응식 17]에 의하여 [화학식 5-a]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 5-a] was synthesized by the following [Scheme 17].
[반응식 17][Reaction Scheme 17]
[화학식 5-a][Formula 5-a]
상기 <합성예 1>의 [반응식 1]과 동일한 방법으로 합성하여 [화학식 5-a]로 표시되는 화합물을 7.6 g (수율 79.6%) 얻었다.
Synthesis was carried out in the same manner as in [Scheme 1] of <Synthesis Example 1>, to obtain 7.6 g (yield 79.6%) of the compound represented by [Formula 5-a].
(2) [화학식 78]로 표시되는 화합물의 합성(2) Synthesis of Compound Represented by Formula 78
하기 [반응식 18]에 의하여 [화학식 78]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 78] was synthesized by the following [Scheme 18].
[반응식 18][Reaction Scheme 18]
[화학식 78](78)
상기 <합성예 1>의 [반응식 7]과 동일한 방법으로 합성하여 [화학식 78]로 표시되는 화합물을 12.1 g(59.5%) 얻었다.Synthesis was carried out in the same manner as in [Scheme 7] of <Synthesis Example 1>, to obtain 12.1 g (59.5%) of the compound represented by [Formula 78].
MS : m/z Anal. Calcd 734.71 [M]+ Found: 734 [M]+; Anal. Calcd. C37H25N5Pt: C, 60.49; H, 3.43; N, 9.53. Found: C, 60.24; H, 3.34; N, 9.68.
MS: m / z Anal. Calcd 734.71 [M] < + > Found: 734 [M] < + >; Anal. Calcd. C 37 H 25 N 5 Pt: C, 60.49; H, 3. 43; N, 9.53. Found: C, 60.24; H, 3. 34; N, 9.68.
<합성예 6> [화학식 90]으로 표시되는 화합물의 제조Synthesis Example 6 Preparation of Compound Represented by Formula 90
(1) [화학식 6-a]로 표시되는 화합물의 합성(1) Synthesis of Compound Represented by Formula (6-a)
하기 [반응식 19]에 의하여 [화학식 6-a]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 6-a] was synthesized by the following Reaction Scheme 19.
[반응식 19]Scheme 19
[화학식 6-a][Chemical Formula 6-a]
1 L 둥근 바닥 플라스크에 2,5-다이브로모나이트로벤젠 100 g(0.56 mol)에 페닐보론산 39.5 g(0.32 mol), 테트라키스(트리페닐포스핀)팔라듐(0) 7.5 g(6.0 mmol), 탄산칼륨 89.6 g(0.65 mol), 다이옥산 500 ml, 테트라하이드로퓨란 500 mL와 물 200 mL를 첨가한 후 12 시간 환류시켰다. 반응 종료 후 상온으로 온도를 내리고 유기층을 분리하고 감압 농축 후 헥산을 사용하여 컬럼크로마토그래피로 분리하고 고체를 건조하여 [화학식 6-a]로 표시되는 화합물을 71.9 g(79.8%) 얻었다.
In a 1 L round-bottom flask, 100 g (0.56 mol) of 2,5-dibromonionibenzene, 39.5 g (0.32 mol) of phenylboronic acid, 7.5 g (6.0 mmol) of tetrakis (triphenylphosphine) palladium (0) After adding 89.6 g (0.65 mol) of potassium carbonate, 500 ml of dioxane, 500 mL of tetrahydrofuran and 200 mL of water, the mixture was refluxed for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, separated from the organic layer, concentrated under reduced pressure, separated by column chromatography using hexane, and dried to obtain 71.9 g (79.8%) of the compound represented by [Formula 6-a].
(2) [화학식 6-b]로 표시되는 화합물의 합성(2) Synthesis of Compound Represented by Formula 6-b
하기 [반응식 20]에 의하여 [화학식 6-b]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 6-b] was synthesized by the following [Scheme 20].
[반응식 20][Reaction Scheme 20]
[화학식 6-b][Chemical Formula 6-b]
1 L 둥근 바닥 플라스크에 [반응식 19]로부터 얻은 [화학식 6-a]로 표시되는 화합물 71.9 g(0.26 mol)과 트리에틸포스핀 360 mL를 넣고 12시간 환류시켰다. 반응 종료 후 상온으로 온도를 내리고 결정을 여과시켰다. 메탄올로 재결정을 실시하고 건조하여 [화학식 6-b]로 표시되는 화합물을 52.4 g(82.4%) 얻었다.
71.9 g (0.26 mol) of the compound represented by [Formula 6-a] obtained from [Scheme 19] and 360 mL of triethylphosphine were added to a 1 L round bottom flask, and the mixture was refluxed for 12 hours. After the reaction was completed, the temperature was lowered to room temperature, and the crystals were filtered. Recrystallization with methanol and drying gave 52.4 g (82.4%) of the compound represented by [Formula 6-b].
(3) [화학식 6-c]로 표시되는 화합물의 합성(3) Synthesis of Compound Represented by Formula 6-c
하기 [반응식 21]에 의하여 [화학식 6-c]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 6-c] was synthesized by the following Reaction Scheme 21.
[반응식 21]Scheme 21
[화학식 6-c][Formula 6-c]
상기 <합성예 1>의 [반응식 1]과 동일한 방법으로 합성하여 [화학식 6-c]로 표시되는 화합물을 37.1 g(70.9%) 얻었다.
Synthesis was carried out in the same manner as in [Scheme 1] of <Synthesis Example 1>, to obtain 37.1 g (70.9%) of the compound represented by [Formula 6-c].
(4) [화학식 6-d]로 표시되는 화합물의 합성(4) Synthesis of Compound Represented by Formula 6-d
하기 [반응식 22]에 의하여 [화학식 6-d]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 6-d] was synthesized by the following [Scheme 22].
[반응식 22][Reaction Scheme 22]
[화학식 6-d][Formula 6-d]
500 mL 둥근 바닥 플라스크에 [반응식 21]로부터 얻은 [화학식 6-c]로 표시되는 화합물 30 g(0.01 mol), 아닐린 10.4 g(0.11 mol), 트리스(다이벤즈리덴아세톤)다이팔라듐(0) 1.7 g(2 mmol), 소듐터셔리부톡사이드 13.4 g과 톨루엔 300 mL를 넣는다. 60 ℃까지 온도를 올린 후 트리터셔리부틸포스핀 0.8 g을 넣고 환류시켰다. 반응 종료 후 여과시켜 감압 농축 후 헥산을 사용하여 컬럼크로마토그래피로 분리하고 고체를 건조하여 [화학식 6-d]로 표시되는 화합물을 27.2 g(87.4%) 얻었다.
In a 500 mL round bottom flask, 30 g (0.01 mol) of compound represented by [Formula 6-c] obtained from [Scheme 21], 10.4 g (0.11 mol) of aniline, tris (dibenzideneacetone) dipalladium (0) 1.7 g (2 mmol), 13.4 g of sodium tert-butoxide and 300 mL of toluene were added thereto. After raising the temperature to 60 ℃ 0.8 g of tributyl butyl phosphine was added to reflux. After completion of the reaction, the mixture was filtered and concentrated under reduced pressure, separated by column chromatography using hexane, and dried to obtain 27.2 g (87.4%) of the compound represented by [Formula 6-d].
(5) [화학식 6-e]로 표시되는 화합물의 합성(5) Synthesis of Compound Represented by Formula 6-e
하기 [반응식 23]에 의하여 [화학식 6-e]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 6-e] was synthesized by the following [Scheme 23].
[반응식 23][Reaction Scheme 23]
[화학식 6-e][Formula 6-e]
상기 <합성예 1>의 [반응식 1]과 동일한 방법으로 합성하여 [화학식 6-e]로 표시되는 화합물을 17.3 g(59.6%) 얻었다.
Synthesis was carried out in the same manner as in [Scheme 1] of <Synthesis Example 1>, to obtain 17.3 g (59.6%) of the compound represented by [Formula 6-e].
(6) [화학식 6-f]로 표시되는 화합물의 합성(6) Synthesis of Compound Represented by Formula 6-f
하기 [반응식 24]에 의하여 [화학식 6-f]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 6-f] was synthesized by the following [Scheme 24].
[반응식 24]Scheme 24
[화학식 6-f][Formula 6-f]
상기 <합성예 1>의 [반응식 5]와 동일한 방법으로 합성하여 [화학식 6-f]로 표시되는 화합물을 14.7 g (수율 65.3%) 얻었다.
Synthesis was carried out in the same manner as in [Scheme 5] of <Synthesis Example 1>, to obtain 14.7 g (yield 65.3%) of the compound represented by [Formula 6-f].
(7) [화학식 6-g]로 표시되는 화합물의 합성(7) Synthesis of Compound Represented by [Formula 6-g]
하기 [반응식 25]에 의하여 [화학식 6-g]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 6-g] was synthesized by the following [Scheme 25].
[반응식 25][Reaction Scheme 25]
[화학식 6-g][Formula 6-g]
상기 <합성예 1>의 [반응식 6]과 동일한 방법으로 합성하여 [화학식 6-g]로 표시되는 화합물을 8.6 g (수율 61.7%) 얻었다
Synthesis was carried out in the same manner as in [Scheme 6] of <Synthesis Example 1> to obtain 8.6 g (yield 61.7%) of the compound represented by [Formula 6-g].
(8) [화학식 90]으로 표시되는 화합물의 합성(8) Synthesis of Compound Represented by Formula 90
하기 [반응식 26]에 의하여 [화학식 90]으로 표시되는 화합물을 합성하였다.The compound represented by [Formula 90] was synthesized by the following [Scheme 26].
[반응식 26][Reaction Scheme 26]
[화학식 90](90)
상기 <합성예 1>의 [반응식 7]과 동일한 방법으로 합성하여 [화학식 90]으로 표시되는 화합물을 10.1 g(54.3%) 얻었다.Synthesis was carried out in the same manner as in [Scheme 7] of <Synthesis Example 1>, to obtain 10.1 g (54.3%) of the compound represented by [Formula 90].
MS : m/z Anal. Calcd 921.94 [M]+ Found: 921 [M]+; Anal. Calcd. C53H34N4Pt: C, 69.05; H, 3.72; N, 6.08. Found: C, 68.93; H, 3.65; N, 5.98.
MS: m / z Anal. Calcd 921.94 [M] < + > Found: 921 [M] < + >; Anal. Calcd. C 53 H 34 N 4 Pt: C, 69.05; H, 3.72; N, 6.08. Found: C, 68.93; H, 3.65; N, 5.98.
<합성예 8> [화학식 91]로 표시되는 화합물의 제조Synthesis Example 8 Preparation of Compound Represented by Formula 91
(1) [화학식 8-a]로 표시되는 화합물의 합성(1) Synthesis of Compound Represented by Formula (8-a)
하기 [반응식 27]에 의하여 [화학식 8-a]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 8-a] was synthesized by the following [Scheme 27].
[반응식 27][Reaction Scheme 27]
[화학식 8-a][Formula 8-a]
상기 <합성예 6>의 [반응식 22]과 동일한 방법으로 합성하여 [화학식 8-a]로 표시되는 화합물을 19.0 g(88.1%) 얻었다.
Synthesis was carried out in the same manner as in Scheme 22 of Synthesis Example 6 to obtain 19.0 g (88.1%) of the compound represented by [Formula 8-a].
(2) [화학식 8-b]로 표시되는 화합물의 합성(2) Synthesis of Compound Represented by Formula (8-b)
하기 [반응식 28]에 의하여 [화학식 8-b]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 8-b] was synthesized by the following Reaction Scheme 28.
[반응식 28][Reaction Scheme 28]
[화학식 8-b][Formula 8-b]
상기 <합성예 1>의 [반응식 1]과 동일한 방법으로 합성하여 [화학식 8-b]로 표시되는 화합물을 20.2 g(73.6%) 얻었다.
Synthesis was carried out in the same manner as in [Scheme 1] of <Synthesis Example 1>, to obtain 20.2 g (73.6%) of the compound represented by [Formula 8-b].
(3) [화학식 8-c]로 표시되는 화합물의 합성(3) Synthesis of Compound Represented by Formula (8-c)
하기 [반응식 29]에 의하여 [화학식 8-c]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 8-c] was synthesized by the following Reaction Scheme 29.
[반응식 29][Reaction Scheme 29]
[화학식 8-c][Formula 8-c]
상기 <합성예 1>의 [반응식 5]와 동일한 방법으로 합성하여 [화학식 8-c]로 표시되는 화합물을 23.3 g (수율 78.9%) 얻었다.
Synthesis was carried out in the same manner as in [Scheme 5] of <Synthesis Example 1>, to obtain 23.3 g (yield 78.9%) of the compound represented by [Formula 8-c].
(4) [화학식 8-d]로 표시되는 화합물의 합성(4) Synthesis of Compound Represented by Formula 8-d
하기 [반응식 30]에 의하여 [화학식 8-d]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 8-d] was synthesized by the following [Scheme 30].
[반응식 30][Reaction Scheme 30]
[화학식 8-d][Formula 8-d]
상기 <합성예 1>의 [반응식 6]과 동일한 방법으로 합성하여 [화학식 8-d]로 표시되는 화합물을 15.4 g (수율 77.4%) 얻었다
Synthesis was carried out in the same manner as in [Scheme 6] of <Synthesis Example 1> to obtain 15.4 g (yield 77.4%) of the compound represented by [Formula 8-d].
(5) [화학식 91]로 표시되는 화합물의 합성(5) Synthesis of Compound Represented by Formula 91
하기 [반응식 31]에 의하여 [화학식 91]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 91] was synthesized by the following [Scheme 31].
[반응식 31][Reaction Scheme 31]
[화학식 91][Formula 91]
상기 <합성예 1>의 [반응식 7]과 동일한 방법으로 합성하여 [화학식 91]로 표시되는 화합물을 9.9 g(52.4%) 얻었다.Synthesis was carried out in the same manner as in [Scheme 7] of <Synthesis Example 1> to obtain 9.9 g (52.4%) of the compound represented by [Formula 91].
MS : m/z Anal. Calcd 935.97 [M]+ Found: 935 [M]+; Anal. Calcd. C54H36N4Pt: C, 69.29; H, 3.88; N, 5.99; Pt, 20.84. Found: C, 69.15; H, 3.76; N, 5.78; Pt, 20.39.
MS: m / z Anal. Calcd 935.97 [M] < + > Found: 935 [M] < + >; Anal. Calcd. C 54 H 36 N 4 Pt: C, 69.29; H, 3.88; N, 5.99; Pt, 20.84. Found: C, 69.15; H, 3.76; N, 5.78; Pt, 20.39.
<합성예 9> [화학식 115]로 표시되는 화합물의 제조Synthesis Example 9 Preparation of Compound Represented by Formula 115
(1) [화학식 9-a]로 표시되는 화합물의 합성(1) Synthesis of Compound Represented by [Formula 9-a]
하기 [반응식 32]에 의하여 [화학식 9-a]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 9-a] was synthesized by the following [Scheme 32].
[반응식 32][Reaction Scheme 32]
[화학식 9-a][Chemical Formula 9-a]
상기 <합성예 1>의 [반응식 2]와 동일한 방법으로 합성하여 [화학식 9-a]로 표시되는 화합물을 11.1 g(45.9%) 얻었다.
Synthesis was carried out in the same manner as in [Reaction Scheme 2] of <Synthesis Example 1>, to obtain 11.1 g (45.9%) of the compound represented by [Formula 9-a].
(2) [화학식 9-b]로 표시되는 화합물의 합성(2) Synthesis of Compound Represented by [Formula 9-b]
하기 [반응식 33]에 의하여 [화학식 9-b]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 9-b] was synthesized by the following [Scheme 33].
[반응식 33][Reaction Scheme 33]
[화학식 9-b][Formula 9-b]
상기 <합성예 1>의 [반응식 3]과 동일한 방법으로 합성하여 [화학식 9-b]로 표시되는 화합물을 13.5 g(45.9%) 얻었다.
Synthesis was carried out in the same manner as in [Scheme 3] of <Synthesis Example 1>, to obtain 13.5 g (45.9%) of the compound represented by [Formula 9-b].
(3) [화학식 9-c]로 표시되는 화합물의 합성(3) Synthesis of Compound Represented by [Formula 9-c]
하기 [반응식 34]에 의하여 [화학식 9-c]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 9-c] was synthesized by the following Reaction Scheme 34.
[반응식 34][Reaction Scheme 34]
[화학식 9-c][Formula 9-c]
상기 <합성예 1>의 [반응식 5]와 동일한 방법으로 합성하여 [화학식 9-c]로 표시되는 화합물을 11.6 g (수율 77.1%) 얻었다.
Synthesis was carried out in the same manner as in [Scheme 5] of <Synthesis Example 1>, to obtain 11.6 g (yield 77.1%) of the compound represented by [Formula 9-c].
(4) [화학식 9-d]로 표시되는 화합물의 합성(4) Synthesis of Compound Represented by Formula 9-d
하기 [반응식 35]에 의하여 [화학식 9-d]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 9-d] was synthesized by the following Reaction Scheme 35.
[반응식 35][Reaction Scheme 35]
[화학식 9-d][Formula 9-d]
상기 <합성예 1>의 [반응식 6]과 동일한 방법으로 합성하여 [화학식 9-d]로 표시되는 화합물을 8.0 g (수율 81.1%) 얻었다.
Synthesis was carried out in the same manner as in [Scheme 6] of <Synthesis Example 1>, and 8.0 g (yield 81.1%) of the compound represented by [Formula 9-d] was obtained.
(5) [화학식 115]로 표시되는 화합물의 합성(5) Synthesis of Compound Represented by Formula 115
하기 [반응식 36]에 의하여 [화학식 115]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 115] was synthesized by the following [Scheme 36].
[반응식 36][Reaction Scheme 36]
[화학식 115][Formula 115]
상기 <합성예 1>의 [반응식 7]과 동일한 방법으로 합성하여 [화학식 115]로 표시되는 화합물을 9.6 g(50.6%) 얻었다.Synthesis was carried out in the same manner as in [Scheme 7] of <Synthesis Example 1> to obtain 9.6 g (50.6%) of the compound represented by [Formula 115].
MS : m/z Anal. Calcd 921.94 [M]+ Found: 921 [M]+; Anal. Calcd. C53H34N4Pt: C, 69.05; H, 3.72; N, 6.08. Found: C, 68.97; H, 3.87; N, 6.13.
MS: m / z Anal. Calcd 921.94 [M] < + > Found: 921 [M] < + >; Anal. Calcd. C 53 H 34 N 4 Pt: C, 69.05; H, 3.72; N, 6.08. Found: C, 68.97; H, 3.87; N, 6.13.
<합성예 10> [화학식 126]으로 표시되는 화합물의 제조Synthesis Example 10 Preparation of Compound Represented by Formula 126
(1) [화학식 10-a]로 표시되는 화합물의 합성(1) Synthesis of Compound Represented by [Formula 10-a]
하기 [반응식 37]에 의하여 [화학식 10-a]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 10-a] was synthesized by the following [Scheme 37].
[반응식 37][Reaction Scheme 37]
[화학식 10-a][Formula 10-a]
상기 <합성예 1>의 [반응식 4]와 동일한 방법으로 합성하여 [화학식 10-a]로 표시되는 화합물을 15.7 g(78.6%) 얻었다.
Synthesis was carried out in the same manner as in [Reaction Scheme 4] of <Synthesis Example 1>, to obtain 15.7 g (78.6%) of a compound represented by [Formula 10-a].
(2) [화학식 10-b]로 표시되는 화합물의 합성(2) Synthesis of Compound Represented by Formula 10-b
하기 [반응식 38]에 의하여 [화학식 10-b]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 10-b] was synthesized by the following [Scheme 38].
[반응식 38][Reaction Scheme 38]
[화학식 10-b][Formula 10-b]
상기 <합성예 1>의 [반응식 6]과 동일한 방법으로 합성하여 [화학식 10-b]로 표시되는 화합물을 6.7 g (수율 69.7%) 얻었다.
Synthesis was carried out in the same manner as in [Scheme 6] of <Synthesis Example 1>, to obtain 6.7 g (yield 69.7%) of the compound represented by [Formula 10-b].
(3) [화학식 126]으로 표시되는 화합물의 합성(3) Synthesis of Compound Represented by Formula 126
하기 [반응식 39]에 의하여 [화학식 126]으로 표시되는 화합물을 합성하였다.The compound represented by [Formula 126] was synthesized by the following [Scheme 39].
[반응식 39][Reaction Scheme 39]
[화학식 126][Formula 126]
상기 <합성예 1>의 [반응식 7]과 동일한 방법으로 합성하여 [화학식 26]으로 표시되는 화합물을 8.6 g(45.8%) 얻었다.Synthesis was carried out in the same manner as in [Scheme 7] of <Synthesis Example 1> to obtain 8.6 g (45.8%) of the compound represented by [Formula 26].
MS : m/z Anal. Calcd 957.92 [M]+ Found: 957 [M]+; Anal. Calcd. C53H32F2N4Pt: C, 66.45; H, 3.37; N, 5.85. Found: C, 66.24; H, 3.25; N, 5.68
MS: m / z Anal. Calcd 957.92 [M] < + >: 957 [M] < + >; Anal. Calcd. C 53 H 32 F 2 N 4 Pt: C, 66.45; H, 3. 37; N, 5.85. Found: C, 66.24; H, 3. 25; N, 5.68
<합성예 11> [화학식 138]로 표시되는 화합물의 제조Synthesis Example 11 Preparation of Compound Represented by Formula 138
(1) [화학식 11-a]로 표시되는 화합물의 합성(1) Synthesis of Compound Represented by Formula 11-a
하기 [반응식 40]에 의하여 [화학식 11-a]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 11-a] was synthesized by the following [Scheme 40].
[반응식 40][Reaction Scheme 40]
[화학식 11-a][Formula 11-a]
상기 <합성예 1>의 [반응식 4]와 동일한 방법으로 합성하여 [화학식 11-a]로 표시되는 화합물을 13.5 g(81.2%) 얻었다.
Synthesis was carried out in the same manner as in [Reaction Scheme 4] of <Synthesis Example 1>, to obtain 13.5 g (81.2%) of a compound represented by [Formula 11-a].
(2) [화학식 11-b]로 표시되는 화합물의 합성(2) Synthesis of Compound Represented by Formula 11-b
하기 [반응식 41]에 의하여 [화학식 11-b]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 11-b] was synthesized by the following [Scheme 41].
[반응식 41][Reaction Scheme 41]
[화학식 11-b][Formula 11-b]
상기 <합성예 1>의 [반응식 6]과 동일한 방법으로 합성하여 [화학식 11-b]로 표시되는 화합물을 9.9 g (수율 88.1%) 얻었다.
Synthesis was carried out in the same manner as in [Scheme 6] of <Synthesis Example 1> to obtain 9.9 g (yield 88.1%) of the compound represented by [Formula 11-b].
(3) [화학식 138]로 표시되는 화합물의 합성(3) Synthesis of Compound Represented by Formula 138
하기 [반응식 42]에 의하여 [화학식 138]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 138] was synthesized by the following [Scheme 42].
[반응식 42][Reaction Scheme 42]
[화학식 138]≪ EMI ID =
상기 <합성예 1>의 [반응식 7]과 동일한 방법으로 합성하여 [화학식 138]로 표시되는 화합물을 10.6 g(57.3%) 얻었다.Synthesis was carried out in the same manner as in [Scheme 7] of <Synthesis Example 1>, to obtain 10.6 g (57.3%) of the compound represented by [Formula 138].
MS : m/z Anal. Calcd 1022.06 [M]+ Found: 1021.27 [M]+; Anal. Calcd. C61H38N4Pt: C, 71.68; H, 3.75; N, 5.48. Found: C, 71.52; H, 3.58; N, 5.39.
MS: m / z Anal. Calcd 1022.06 [M] < + > Found: 1021.27 [M] < + >; Anal. Calcd. C 61 H 38 N 4 Pt: C, 71.68; H, 3.75; N, 5.48. Found: C, 71.52; H, 3.58; N, 5.39.
<합성예 12> [화학식 162]로 표시되는 화합물의 제조Synthesis Example 12 Preparation of Compound Represented by Formula 162
(1) [화학식 12-a]로 표시되는 화합물의 합성(1) Synthesis of Compound Represented by Formula 12-a
하기 [반응식 43]에 의하여 [화학식 12-a]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 12-a] was synthesized by the following [Scheme 43].
[반응식 43][Reaction Scheme 43]
[화학식 12-a][Formula 12-a]
상기 <합성예 1>의 [반응식 1]과 동일한 방법으로 합성하여 [화학식 5-a]로 표시되는 화합물을 5.7 g (수율 59.6%) 얻었다.
Synthesis was carried out in the same manner as in [Scheme 1] of <Synthesis Example 1>, to obtain 5.7 g (yield 59.6%) of the compound represented by [Formula 5-a].
(2) [화학식 162]로 표시되는 화합물의 합성(2) Synthesis of Compound Represented by Formula 162
하기 [반응식 44]에 의하여 [화학식 162]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 162] was synthesized by the following [Scheme 44].
[반응식 44][Reaction Scheme 44]
[화학식 162][Formula 162]
상기 <합성예 1>의 [반응식 7]과 동일한 방법으로 합성하여 [화학식 162]로 표시되는 화합물을 10.6 g(55.5%) 얻었다.Synthesis was carried out in the same manner as in [Scheme 7] of <Synthesis Example 1>, to obtain 10.6 g (55.5%) of the compound represented by [Formula 162].
MS : m/z Anal. Calcd 899.9 [M]+ Found: 899.23 [M]+; Anal. Calcd. C49H32N6Pt: C, 65.40; H, 3.58; N, 9.34. Found: C, 65.86; H, 3.51; N, 9.46.
MS: m / z Anal. Calcd 899.9 [M] < + > Found: 899.23 [M] < + >; Anal. Calcd. C 49 H 32 N 6 Pt: C, 65.40; H, 3.58; N, 9.34. Found: C, 65.86; H, 3.51; N, 9.46.
<합성예 13> [화학식 170]으로 표시되는 화합물의 제조Synthesis Example 13 Preparation of Compound Represented by Formula 170
(1) [화학식 13-a]로 표시되는 화합물의 합성(1) Synthesis of Compound Represented by [Formula 13-a]
하기 [반응식 45]에 의하여 [화학식 13-a]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 13-a] was synthesized by the following [Scheme 45].
[반응식 45][Reaction Scheme 45]
[화학식 13-a][Formula 13-a]
상기 <합성예 1>의 [반응식 4]와 동일한 방법으로 합성하여 [화학식 13-a]로 표시되는 화합물을 12.4 g(71.1%) 얻었다.
Synthesis was carried out in the same manner as in [Scheme 4] of <Synthesis Example 1>, to obtain 12.4 g (71.1%) of a compound represented by [Formula 13-a].
(2) [화학식 13-b]로 표시되는 화합물의 합성(2) Synthesis of Compound Represented by [Formula 13-b]
하기 [반응식 46]에 의하여 [화학식 13-b]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 13-b] was synthesized by the following [Scheme 46].
[반응식 46][Reaction Scheme 46]
[화학식 13-b][Chemical Formula 13-b]
2 L 둥근 바닥 플라스크에 다이페닐아민 51 g(0.3 mol)과 에틸 아세테이트 700 mL를 넣었다. 엔-브로모숙시니이드 54 g(0.3 mol) 넣고 30 시간 동안 교반하였다. 반응 종료 후 물로 반응을 종결시키고 추출한 뒤 유기층을 감압농축 후 헥산으로 재결정을 실시하고 건조하여 [화학식 13-b]로 표시되는 화합물을 70 g(94%) 얻었다.
Into a 2 L round bottom flask was placed 51 g (0.3 mol) of diphenylamine and 700 mL of ethyl acetate. 54 g (0.3 mol) of N-bromosuccinate was added and stirred for 30 hours. After completion of the reaction, the reaction was terminated with water and extracted, the organic layer was concentrated under reduced pressure, recrystallized with hexane and dried to give 70 g (94%) of the compound represented by the formula (13-b).
(3) [화학식 13-c]로 표시되는 화합물의 합성(3) Synthesis of Compound Represented by [Formula 13-c]
하기 [반응식 47]에 의하여 [화학식 13-c]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 13-c] was synthesized by the following [Scheme 47].
[반응식 47][Reaction Scheme 47]
[화학식 13-c][Formula 13-c]
상기 <합성예 1>의 [반응식 6]과 동일한 방법으로 합성하여 [화학식 13-c]로 표시되는 화합물을 12.2 g (수율 83.6%) 얻었다
Synthesis was carried out in the same manner as in [Scheme 6] of <Synthesis Example 1> to obtain 12.2 g (yield 83.6%) of the compound represented by [Formula 13-c].
(4) [화학식 13-d]로 표시되는 화합물의 합성(4) Synthesis of Compound Represented by Formula 13-d
하기 [반응식 48]에 의하여 [화학식 13-d]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 13-d] was synthesized by the following [Scheme 48].
[반응식 48][Reaction Scheme 48]
[화학식 13-d][Formula 13-d]
상기 <합성예 1>의 [반응식 1]과 동일한 방법으로 합성하여 [화학식 13-d]로 표시되는 화합물을 12.8 g(75.1%) 얻었다.
Synthesis was carried out in the same manner as in [Scheme 1] of <Synthesis Example 1>, and 12.8 g (75.1%) of a compound represented by [Formula 13-d] was obtained.
(5) [화학식 13-e]로 표시되는 화합물의 합성(5) Synthesis of Compound Represented by Formula 13-e
하기 [반응식 49]에 의하여 [화학식 9-e]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 9-e] was synthesized by the following [Scheme 49].
[반응식 49][Reaction Scheme 49]
[화학식 13-e][Formula 13-e]
상기 <합성예 1>의 [반응식 5]와 동일한 방법으로 합성하여 [화학식 13-e]로 표시되는 화합물을 13.6 g (수율 68.9%) 얻었다.
Synthesis was carried out in the same manner as in [Scheme 5] of <Synthesis Example 1>, to obtain 13.6 g (yield 68.9%) of the compound represented by [Formula 13-e].
(6) [화학식 13-f]로 표시되는 화합물의 합성(6) Synthesis of Compound Represented by Formula 13-f
하기 [반응식 50]에 의하여 [화학식 13-f]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 13-f] was synthesized by the following [Scheme 50].
[반응식 50][Reaction Scheme 50]
[화학식 13-f][Formula 13-f]
상기 <합성예 1>의 [반응식 6]과 동일한 방법으로 합성하여 [화학식 13-f]로 표시되는 화합물을 9.4 g (수율 78.4%) 얻었다
Synthesis was carried out in the same manner as in [Scheme 6] of <Synthesis Example 1> to obtain 9.4 g (yield 78.4%) of the compound represented by [Formula 13-f].
(7) [화학식 170]으로 표시되는 화합물의 합성(7) Synthesis of Compound Represented by Formula 170
하기 [반응식 51]에 의하여 [화학식 170]으로 표시되는 화합물을 합성하였다.The compound represented by [Formula 170] was synthesized by the following [Scheme 51].
[반응식 51][Reaction Scheme 51]
[화학식 170](170)
상기 <합성예 1>의 [반응식 7]과 동일한 방법으로 합성하여 [화학식 170]으로 표시되는 화합물을 10.5 g(55.8%) 얻었다.Synthesis was carried out in the same manner as in [Scheme 7] of <Synthesis Example 1>, to obtain 10.5 g (55.8%) of the compound represented by [Formula 170].
MS : m/z Anal. Calcd 949.28 [M]+ Found: 948 [M]+; Anal. Calcd. C56H39N3Pt: C, 70.87; H, 4.14; N, 4.43. Found: C, 70.76; H, 4.05; N, 4.56.
MS: m / z Anal. Calcd 949.28 [M] < + > Found: 948 [M] < + >; Anal. Calcd. C 56 H 39 N 3 Pt: C, 70.87; H, 4.14; N, 4.43. Found: C, 70.76; H, 4.05; N, 4.56.
<합성예 13 > [화학식 171]로 표시되는 화합물의 제조Synthesis Example 13 Preparation of Compound Represented by Formula 171
(1) [화학식 13-a]로 표시되는 화합물의 합성(1) Synthesis of Compound Represented by [Formula 13-a]
하기 [반응식 52]에 의하여 [화학식 13-a]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 13-a] was synthesized by the following [Scheme 52].
[반응식 52][Reaction Scheme 52]
[화학식 13-a][Formula 13-a]
상기 <합성예 1>의 [반응식 1]과 동일한 방법으로 합성하여 [화학식 13-a]로 표시되는 화합물을 9.9 g (수율 88.1%) 얻었다
Synthesis was carried out in the same manner as in [Scheme 1] of <Synthesis Example 1> to obtain 9.9 g (yield 88.1%) of the compound represented by [Formula 13-a].
(2) [화학식 13-b]로 표시되는 화합물의 합성(2) Synthesis of Compound Represented by [Formula 13-b]
하기 [반응식 53]에 의하여 [화학식 13-b]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 13-b] was synthesized by the following [Scheme 53].
[반응식 53][Reaction Scheme 53]
[화학식 13-b][Chemical Formula 13-b]
상기 <합성예 6>의 [반응식 22]와 동일한 방법으로 합성하여 [화학식 6-c]로 표시되는 화합물을 7.0 g(68.1%) 얻었다.
Synthesis was carried out in the same manner as in [Scheme 22] of <Synthesis Example 6> to obtain 7.0 g (68.1%) of the compound represented by [Formula 6-c].
(3) [화학식 13-c]로 표시되는 화합물의 합성(3) Synthesis of Compound Represented by [Formula 13-c]
하기 [반응식 54]에 의하여 [화학식 13-c]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 13-c] was synthesized by the following [Scheme 54].
[반응식 54][Reaction Scheme 54]
[화학식 13-c][Formula 13-c]
상기 <합성예 1>의 [반응식 1]과 동일한 방법으로 합성하여 [화학식 13-c]로 표시되는 화합물을 7.3 g (수율 78.2%) 얻었다
Synthesis was carried out in the same manner as in [Scheme 1] of <Synthesis Example 1> to obtain 7.3 g (yield 78.2%) of the compound represented by [Formula 13-c].
(5) [화학식 13-d]로 표시되는 화합물의 합성(5) Synthesis of Compound Represented by Formula 13-d
하기 [반응식 55]에 의하여 [화학식 13-d]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 13-d] was synthesized by the following [Scheme 55].
[반응식 55][Reaction Scheme 55]
[화학식 13-d][Formula 13-d]
상기 <합성예 1>의 [반응식 5]와 동일한 방법으로 합성하여 [화학식 13-d]로 표시되는 화합물을 5.1 g (수율 52.1%) 얻었다.
Synthesis was carried out in the same manner as in [Scheme 5] of <Synthesis Example 1>, and 5.1 g (yield 52.1%) of the compound represented by [Formula 13-d] was obtained.
(6) [화학식 13-e]로 표시되는 화합물의 합성(6) Synthesis of Compound Represented by Formula 13-e
하기 [반응식 56]에 의하여 [화학식 13-e]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 13-e] was synthesized by the following [Scheme 56].
[반응식 56][Reaction Scheme 56]
[화학식 13-e][Formula 13-e]
상기 <합성예 1>의 [반응식 6]과 동일한 방법으로 합성하여 [화학식 13-e]로 표시되는 화합물을 4.5 g (수율 81.1%) 얻었다.
Synthesis was carried out in the same manner as in [Scheme 6] of <Synthesis Example 1>, and 4.5 g (yield 81.1%) of the compound represented by [Formula 13-e] was obtained.
(7) [화학식 171]로 표시되는 화합물의 합성(7) Synthesis of Compound Represented by Formula 171
하기 [반응식 57]에 의하여 [화학식 171]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 171] was synthesized by the following [Scheme 57].
[반응식 57][Reaction Scheme 57]
[화학식 171][171]
상기 <합성예 1>의 [반응식 7]과 동일한 방법으로 합성하여 [화학식 171]로 표시되는 화합물을 2.7 g(48.3%) 얻었다.Synthesis was carried out in the same manner as in [Scheme 7] of <Synthesis Example 1> to obtain 2.7 g (48.3%) of the compound represented by [Formula 171].
MS : m/z Anal. Calcd 1038.1 [M]+ Found: 1037.31 [M]+; Anal. Calcd. C62H42N4Pt: C, 71.73; H, 4.08; N, 5.40; Pt, 18.79. Found: C, 71.52; H, 4.03; N, 5.52; Pt, 19.03.
MS: m / z Anal. Calcd 1038.1 [M] < + > Found: 1037.31 [M] < + >; Anal. Calcd. C 62 H 42 N 4 Pt: C, 71.73; H, 4.08; N, 5.40; Pt, 18.79. Found: C, 71.52; H, 4.03; N, 5.52; Pt, 19.03.
<실시예 1 내지 13> 유기전계발광소자의 제조Examples 1 to 13 Fabrication of Organic Electroluminescent Device
ITO 글래스의 발광 면적이 2 mm × 2 mm 크기가 되도록 패터닝한 후 세정하였다. 기판을 진공 챔버에 장착한 후 베이스 압력이 1 × 10-6 torr가 되도록 한 후 유기물을 상기 ITO 위에 DNTPD(700Å), NPD(300Å), CBP + 본 발명에 의해 제조된 화합물(7%)(300Å), Alq3(350Å), LiF(5Å), Al(1,000Å)의 순서로 성막하였으며, 0.4 mA에서 측정을 하였다.The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After mounting the substrate in a vacuum chamber, the base pressure is 1 × 10 -6 torr, and the organic material is placed on the ITO DNTPD (700 kPa), NPD (300 kPa), CBP + the compound (7%) prepared by the present invention ( 300 Å), Alq 3 (350 Å), LiF (5 Å), and Al (1,000 Å) were formed in this order, and measured at 0.4 mA.
[DNTPD][DNTPD]
[NPD][NPD]
[CBP][CBP]
[Alq3][Alq 3 ]
<비교예 1>≪ Comparative Example 1 &
비교예를 위한 유기전계발광소자는 상기 실시예 1 내지 13의 소자 구조에서 발명에 의해 제조된 화합물 대신 하기 구조식의 BTPIr을 사용한 점을 제외하고 동일하게 제작하였다.The organic light emitting display device for the comparative example was manufactured in the same manner except for using the BTPIr of the following structural formula instead of the compound prepared by the invention in the device structure of Examples 1 to 13.
[BTPIr][BTPIr]
본 발명의 [화학식 18], [화학식 21], [화학식 30], [화학식 37], [화학식 78], [화학식 162], [화학식 170] 및 [화학식 171]의 밴드갭을 측정하기 위하여 흡수분광광도계(UV/Vis absorption spectrometer) 및 전압전류계(Cyclic voltammetry)을 이용하여 측정하였고, 그 결과를 하기 [표 2]에 나타내었다.Absorption to measure the bandgap of [Formula 18], [Formula 21], [Formula 30], [Formula 37], [Formula 78], [Formula 162], [Formula 170] and [Formula 171] of the present invention. Measurement was performed using a spectrophotometer (UV / Vis absorption spectrometer) and a cyclic voltammetry, and the results are shown in the following [Table 2].
이상과 같이, 상기 실시예 1 내지 13, 비교예 1, [표 1] 및 [표 2]의 결과로부터, 본 발명에 따른 [화학식 1]로 표시되는 화합물은 인광발광재료로 많이 쓰이는 BTPIr에 비하여 열적특성 및 발광효율 등이 우수한 특성을 보이므로, 표시소자, 디스플레이 소자 및 조명 등에 유용하게 사용될 수 있음을 알 수 있다.As described above, from the results of Examples 1 to 13, Comparative Example 1, Table 1, and Table 2, the compound represented by
10 : 기판 20 : 애노드
30 : 정공주입층 40 : 정공수송층
50 : 유기발광층 60 : 전자수송층
70 : 전자주입층 80 : 캐소드10: substrate 20: anode
30: hole injection layer 40: hole transport layer
50: organic light emitting layer 60: electron transport layer
70: electron injection layer 80: cathode
Claims (8)
[화학식 1]
상기 [화학식 1]에서,
상기 복수의 R 및 복수의 Z는 각각 독립적으로 수소, 중수소, 시아노기, 할로겐, 히드록시기, 니트로기, 탄소수 1-40의 알킬기, 탄소수 1-40의 알콕시기, 탄소수 1-40의 알킬아미노기, 탄소수 6-40의 아릴아미노기, 탄소수 3-40의 헤테로아릴아미노기, 탄소수 1-40의 알킬실릴기, 탄소수 6-40의 아릴실릴기, 탄소수 6-40의 아릴기, 탄소수 3-40의 아릴옥시기, 탄소수 3-40의 헤테로아릴기, 게르마늄기, 인, 보론으로 이루어진 군으로부터 선택되고,
상기 A1 내지 A8은 각각 독립적으로 탄소수 6-40의 방향족 고리, 탄소수 3-40의 헤테로 고리이며,
상기 B는 탄소 및 질소, 실리콘원자이고,
상기 D1 및 D2는 각각 독립적으로 화학결합, C, N, O, S 및 Si 중에서 선택되며,
상기 복수의 X는 각각 독립적으로 C 또는 N이고, 상기 복수의 X 중 적어도 두 개 이상은 백금 금속에 배위하는 N을 포함하고,
상기 복수의 G는 각각 독립적으로 화학결합, 탄소수 1-4의 알킬렌 또는 (R-Zi)n이 치환된 탄소수 1-4의 알킬렌이며,
상기 n 및 i는 각각 독립적으로 1 내지 40의 정수이고, 상기 n 및 i가 2 이상인 경우 상기 복수의 R 및 복수의 Z는 각각 독립적으로 동일하거나 상이하고,
상기 e는 0 내지 2의 정수이며,
상기 [화학식 1]에서 인접한 작용기는 서로 결합하여 포화 또는 불포화 고리 및 헤테로 원자를 갖는 포화 또는 불포화 고리를 형성할 수 있다.An organometallic compound represented by the following [Formula 1]:
[Formula 1]
In [Formula 1],
The plurality of R and the plurality of Z are each independently hydrogen, deuterium, cyano group, halogen, hydroxy group, nitro group, alkyl group of 1-40 carbon atoms, alkoxy group of 1-40 carbon atoms, alkylamino group of 1-40 carbon atoms, carbon number 6-40 arylamino group, C3-40 heteroarylamino group, C1-40 alkylsilyl group, C6-40 arylsilyl group, C6-40 aryl group, C3-40 aryloxy group , A heteroaryl group having 3 to 40 carbon atoms, a germanium group, phosphorus and boron;
A1 to A8 are each independently an aromatic ring having 6 to 40 carbon atoms and a hetero ring having 3 to 40 carbon atoms,
B is carbon, nitrogen, silicon atoms,
The D1 and D2 are each independently selected from chemical bonds, C, N, O, S and Si,
Each of the plurality of Xs is independently C or N, and at least two or more of the plurality of Xs include N coordinating to a platinum metal,
The plurality of Gs are each independently a chemical bond, alkylene having 1 to 4 carbon atoms or alkylene having 1 to 4 carbon atoms substituted with (R-Zi) n,
N and i are each independently an integer of 1 to 40, when n and i are 2 or more, the plurality of R and a plurality of Z are each independently the same or different,
E is an integer of 0 to 2,
Adjacent functional groups in [Formula 1] may combine with each other to form a saturated or unsaturated ring having a saturated or unsaturated ring and a hetero atom.
상기 [화학식 1]은 하기 [화학식 2] 내지 [화학식 17]로 표시되는 군으로부터 선택되는 어느 하나인 것을 특징으로 하는 유기금속 화합물:
[화학식 2] [화학식 3] [화학식 4] [화학식 5]
[화학식 6] [화학식 7] [화학식 8] [화학식 9]
[화학식 10] [화학식 11] [화학식 12] [화학식 13]
[화학식 14] [화학식 15] [화학식 16] [화학식 17]
상기 [화학식 2] 내지 [화학식 17]에서, 상기 R, A1 내지 A8, B, D, X, Z, n 및 i는 상기 [화학식 1]의 정의와 동일하다.The method of claim 1,
[Formula 1] is an organometallic compound, characterized in that any one selected from the group represented by the following [Formula 2] to [Formula 17]:
[Chemical Formula 2] < EMI ID =
[Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9]
[Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13]
[Chemical Formula 14] [Chemical Formula 15]
In [Formula 2] to [Formula 17], wherein R, A1 to A8, B, D, X, Z, n and i are the same as the definition of [Formula 1].
상기 [화학식 1]은 [화학식 18] 내지 [화학식 177]로 표시되는 군으로부터 선택되는 어느 하나인 것을 특징으로 하는 유기금속 화합물:
[화학식 18] [화학식 19] [화학식 20] [화학식 21]
[화학식 22] [화학식 23] [화학식 24] [화학식 25]
[화학식 26] [화학식 27] [화학식 28] [화학식 29]
[화학식 30] [화학식 31] [화학식 32] [화학식 33]
[화학식 34] [화학식 35] [화학식 36] [화학식 37]
[화학식 38] [화학식 39] [화학식 40] [화학식 41]
[화학식 42] [화학식 43] [화학식 44] [화학식 45]
[화학식 46] [화학식 47] [화학식 48] [화학식 49]
[화학식 50] [화학식 51] [화학식 52] [화학식 53]
[화학식 54] [화학식 55] [화학식 56] [화학식 57]
[화학식 58] [화학식 59] [화학식 60] [화학식 61]
[화학식 62] [화학식 63] [화학식 64] [화학식 65]
[화학식 66] [화학식 67] [화학식 68] [화학식 69]
[화학식 70] [화학식 71] [화학식 72] [화학식 73]
[화학식 74] [화학식 75] [화학식 76] [화학식 77]
[화학식 78] [화학식 79] [화학식 80] [화학식 81]
[화학식 82] [화학식 83] [화학식 84] [화학식 85]
[화학식 86] [화학식 87] [화학식 88] [화학식 89]
[화학식 90] [화학식 91] [화학식 92] [화학식 93]
[화학식 94] [화학식 95] [화학식 96] [화학식 97]
[화학식 98] [화학식 99] [화학식 100] [화학식 101]
[화학식 102] [화학식 103] [화학식 104] [화학식 105]
[화학식 106] [화학식 107] [화학식 108] [화학식 109]
[화학식 110] [화학식 111] [화학식 112] [화학식 113]
[화학식 114] [화학식 115] [화학식 116] [화학식 117]
[화학식 118] [화학식 119] [화학식 120] [화학식 121]
[화학식 122] [화학식 123] [화학식 124] [화학식 125]
[화학식 126] [화학식 127] [화학식 128] [화학식 129]
[화학식 130] [화학식 131] [화학식 132] [화학식 133]
[화학식 134] [화학식 135] [화학식 136] [화학식 137]
[화학식 138] [화학식 139] [화학식 140] [화학식 141]
[화학식 142] [화학식 143] [화학식 144] [화학식 145]
[화학식 146] [화학식 147] [화학식 148] [화학식 149]
[화학식 150] [화학식 151] [화학식 152] [화학식 153]
[화학식 154] [화학식 155] [화학식 156] [화학식 157]
[화학식 158] [화학식 159] [화학식 160] [화학식 161]
[화학식 162] [화학식 163] [화학식 164] [화학식 165]
[화학식 166] [화학식 167] [화학식 168] [화학식 169]
[화학식 170] [화학식 171] [화학식 172] [화학식 173]
[화학식 174] [화학식 175] [화학식 176] [화학식 177]
[Formula 1] is an organometallic compound, characterized in that any one selected from the group represented by [Formula 18] to [Formula 177]:
[Chemical Formula 20] [Chemical Formula 20]
[Chemical Formula 22] [Chemical Formula 23] [Chemical Formula 25]
[Chemical Formula 28] [Chemical Formula 28]
[Chemical Formula 32] [Chemical Formula 32]
[Chemical Formula 35] [Chemical Formula 35]
[Chemical Formula 40] [Chemical Formula 40] [Chemical Formula 40]
[Chemical Formula 43] [Chemical Formula 44] [Chemical Formula 45]
[Chemical Formula 48] [Chemical Formula 48] [Chemical Formula 48]
[Chemical Formula 51] [Chemical Formula 52] [Chemical Formula 53]
[Chemical Formula 55] [Chemical Formula 55] [Chemical Formula 55]
[Chemical Formula 60] [Chemical Formula 61]
[Chemical Formula 62] [Chemical Formula 65] [Chemical Formula 65]
[Chemical Formula 67] [Chemical Formula 68] [Chemical Formula 69]
[Chemical Formula 71] [Chemical Formula 72] [Chemical Formula 73]
[Chemical Formula 75] [Chemical Formula 76] [Chemical Formula 77]
[Formula 79] [Formula 80] [Formula 81]
[Chemical Formula 82]
[Chemical Formula 88] [Chemical Formula 88] [Chemical Formula 89]
[Chemical Formula 91] [Chemical Formula 92] [Chemical Formula 93]
[Chemical Formula 95] [Chemical Formula 96] [Chemical Formula 97]
[Chemical Formula 100] [Chemical Formula 100]
[Formula 103] [Formula 103]
[Chemical Formula 10] [Chemical Formula 10] [Chemical Formula 10] [Chemical Formula 10]
[Formula 110] [Formula 111] [Formula 112] [Formula 113]
[Chemical Formula 115]
[Chemical Formula 120] [Chemical Formula 120] [Chemical Formula 120]
[Formula 124] [Formula 124] [Formula 125]
[Formula 126] < EMI ID = 129.1 >
[Formula 130] < EMI ID = 131.0 >
[Formula 135] [Formula 135] [Formula 137]
[Chemical Formula 140] [Chemical Formula 140] [Chemical Formula 140]
[Chemical Formula 144] [Chemical Formula 144] [Chemical Formula 145]
[Chemical Formula 146] [Chemical Formula 148] [Chemical Formula 149]
[Formula 15] [Formula 15] [Formula 15] [Formula 15]
[Chemical Formula 155] [Chemical Formula 156] [Chemical Formula 157]
[Formula 15] [Formula 15] [Formula 15] [Formula 15] [Formula 15]
[166] [165] [165]
[Formula 166] [Formula 169] [Formula 169]
[173] [173] [173]
[Formula 177] [Formula 177] [Formula 177]
캐소드; 및
상기 애노드와 상기 캐소드 사이에 개재되며, 제 1 항 내지 제 3 항 중 어느 한 항의 화합물을 포함하는 유기전계발광소자.Anode;
Cathode; And
An organic electroluminescent device interposed between the anode and the cathode and comprising the compound of any one of claims 1 to 3.
상기 화합물은 상기 애노드와 상기 캐소드 사이의 발광층 중에 포함되는 것을 특징으로 하는 유기전계발광소자.The method of claim 4, wherein
The compound is an organic light emitting device, characterized in that contained in the light emitting layer between the anode and the cathode.
상기 애노드 및 캐소드 사이에 정공주입층, 정공수송층, 전자저지층, 정공저지층, 전자수송층 및 전자주입층으로 이루어진 군으로부터 선택된 하나 이상의 층을 더 포함하는 것을 특징으로 하는 유기전계발광소자.The method of claim 5, wherein
Wherein at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, an electron blocking layer, a hole blocking layer, an electron transporting layer and an electron injecting layer is further interposed between the anode and the cathode.
상기 정공주입층, 정공수송층, 전자저지층, 발광층, 정공저지층, 전자수송층 및 전자주입층으로부터 선택된 하나 이상의 층은 단분자 증착방식 또는 용액공정에 의하여 형성되는 것을 특징으로 하는 유기전계발광소자.The method according to claim 6,
Wherein at least one layer selected from the group consisting of the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer is formed by a single molecular deposition method or a solution process.
상기 유기전계발광소자는 표시소자, 디스플레이 소자, 또는 단색 또는 백색 조명용 소자에 사용되는 것을 특징으로 하는 유기전계발광소자.The method of claim 4, wherein
The organic electroluminescent device is an organic electroluminescent device, characterized in that used for a display device, a display device, or a device for monochrome or white illumination.
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