KR100537620B1 - 카바졸 함유 화합물 및 이를 이용한 유기 전계 발광 소자 - Google Patents
카바졸 함유 화합물 및 이를 이용한 유기 전계 발광 소자 Download PDFInfo
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- KR100537620B1 KR100537620B1 KR10-2003-0075803A KR20030075803A KR100537620B1 KR 100537620 B1 KR100537620 B1 KR 100537620B1 KR 20030075803 A KR20030075803 A KR 20030075803A KR 100537620 B1 KR100537620 B1 KR 100537620B1
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- South Korea
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- substituted
- unsubstituted
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- hydrogen
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 52
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 239000002019 doping agent Substances 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- -1 R 14 Chemical compound 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 150000002483 hydrogen compounds Chemical class 0.000 claims description 7
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 35
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 abstract description 11
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000000126 substance Substances 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- 238000002347 injection Methods 0.000 description 12
- 239000007924 injection Substances 0.000 description 12
- 239000000758 substrate Substances 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 7
- 238000005424 photoluminescence Methods 0.000 description 7
- 239000010408 film Substances 0.000 description 6
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 6
- 230000007704 transition Effects 0.000 description 6
- 239000004926 polymethyl methacrylate Substances 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical group C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000103 photoluminescence spectrum Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- ROEQGIFOWRQYHD-UHFFFAOYSA-N (2-methoxyphenyl)boronic acid Chemical compound COC1=CC=CC=C1B(O)O ROEQGIFOWRQYHD-UHFFFAOYSA-N 0.000 description 2
- LPUADDUFTHFISB-UHFFFAOYSA-N 1,3,5-tris(2-methoxyphenyl)benzene Chemical compound COC1=CC=CC=C1C1=CC(C=2C(=CC=CC=2)OC)=CC(C=2C(=CC=CC=2)OC)=C1 LPUADDUFTHFISB-UHFFFAOYSA-N 0.000 description 2
- HDFKSISWYLVIKY-UHFFFAOYSA-N 1,3,5-tris(5-bromo-2-methoxyphenyl)benzene Chemical compound COC1=CC=C(Br)C=C1C1=CC(C=2C(=CC=C(Br)C=2)OC)=CC(C=2C(=CC=C(Br)C=2)OC)=C1 HDFKSISWYLVIKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical group C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- PFCFKYSBIQBHAO-UHFFFAOYSA-N lithium;methoxybenzene Chemical compound [Li+].COC1=CC=CC=[C-]1 PFCFKYSBIQBHAO-UHFFFAOYSA-N 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- YWDUZLFWHVQCHY-UHFFFAOYSA-N 1,3,5-tribromobenzene Chemical compound BrC1=CC(Br)=CC(Br)=C1 YWDUZLFWHVQCHY-UHFFFAOYSA-N 0.000 description 1
- SXWIAEOZZQADEY-UHFFFAOYSA-N 1,3,5-triphenylbenzene Chemical compound C1=CC=CC=C1C1=CC(C=2C=CC=CC=2)=CC(C=2C=CC=CC=2)=C1 SXWIAEOZZQADEY-UHFFFAOYSA-N 0.000 description 1
- FMOZIATXSMLFJS-UHFFFAOYSA-N 1-[2-cyclohexyloxy-4-ethoxy-5-(2-methoxyphenoxy)-3-phenoxy-6-propan-2-yloxyphenoxy]naphthalene Chemical group COC1=C(C=CC=C1)OC1=C(C(=C(C(=C1OCC)OC1=CC=CC=C1)OC1CCCCC1)OC1=CC=CC2=CC=CC=C12)OC(C)C FMOZIATXSMLFJS-UHFFFAOYSA-N 0.000 description 1
- HTDQSWDEWGSAMN-UHFFFAOYSA-N 1-bromo-2-methoxybenzene Chemical compound COC1=CC=CC=C1Br HTDQSWDEWGSAMN-UHFFFAOYSA-N 0.000 description 1
- NLWCWEGVNJVLAX-UHFFFAOYSA-N 1-methoxy-2-phenylbenzene Chemical compound COC1=CC=CC=C1C1=CC=CC=C1 NLWCWEGVNJVLAX-UHFFFAOYSA-N 0.000 description 1
- KETXQNLMOUVTQB-UHFFFAOYSA-N 2,3,7,8,12,13,17,18-octaethylporphyrin;platinum Chemical compound [Pt].C=1C(C(=C2CC)CC)=NC2=CC(C(=C2CC)CC)=NC2=CC(C(=C2CC)CC)=NC2=CC2=NC=1C(CC)=C2CC KETXQNLMOUVTQB-UHFFFAOYSA-N 0.000 description 1
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-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
- 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
- KDEMOTIGGJVNOF-UHFFFAOYSA-N COC(C=CC(Br)=C1)=C1C1=CC=CC(C(C=C(C=C2)Br)=C2OC)=C1C(C=C(C=C1)Br)=C1OC Chemical compound COC(C=CC(Br)=C1)=C1C1=CC=CC(C(C=C(C=C2)Br)=C2OC)=C1C(C=C(C=C1)Br)=C1OC KDEMOTIGGJVNOF-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
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910019015 Mg-Ag Inorganic materials 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 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
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003342 alkenyl group Chemical group 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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 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
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 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
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical group C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
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Abstract
Description
Claims (6)
- 하기 화학식 1로 표시되는 카바졸 함유 화합물:[화학식 1]상기식중, R1~ R39은 서로에 관계없이 수소 원자, 시아노기, 하이드록시기, 티올기, 할로겐 원자, 치환 또는 비치환된 C1-C30의 알킬기, 치환 또는 비치환된 C1-C30의 알콕시기, 치환 또는 비치환된 C2-C30의 알케닐기, 치환 또는 비치환된 C2-C30의 알킬카르보닐기, 치환 또는 비치환된 C6-C30의 아릴기, 치환 또는 비치환된 C7-C30의 아릴카르보닐기, 치환 또는 비치환된 C6-C30의 아릴알킬기, 치환 또는 비치환된 C6-C30의 아릴옥시기, 치환 또는 비치환된 C2-C30의 헤테로아릴기, 치환 또는 비치환된 C2-C30의 헤테로아릴알킬기, 치환 또는 비치환된 C2-C30의 헤테로아릴옥시기, 치환 또는 비치환된 C2-C30의 헤테로아릴알킬옥시기, 치환 또는 비치환된 C5-C30의 사이클로알킬기, 치환 또는 비치환된 C2-C30의 헤테로사이클로알킬기, 치환 또는 비치환된 C1-C30의 알킬티오기 또는 -Si(R')(R")(R"')(상기식중, R'과 R''는 서로에 관계없이 수소 또는 C1-C30의 알킬기), -N(R')(R'')(상기식중, R'과 R''는 서로에 관계없이 수소 또는 C1-C30의 알킬기)이고, 또는 상기 R4~R6, R 8~R10, R12~R14, R16~R19, R20~R23, R 24~R27, R28~R31, R32~R35, R 36~R39중에서 선택된 서로 인접된 둘 이상의 치환기가 서로 연결되어 불포화 또는 포화 고리를 형성한다.
- 제1항에 있어서, 상기 화합물이 상기 화학식 1에서 R6, R8 및 R12는 모두 메톡시기이고, R1~R5, R7, R9, R10, R11 , R13~R39은 모두 수소인 화합물;상기 화학식 1에서 상기 R6, R8 및 R12는 모두 메틸기이고, R1 ~R5, R7, R9, R10, R11, R13~R39은 모두 수소인 화합물;상기 화학식 1에서 상기 R4, R7, R10, R11, R14 및 R15는 모두 메틸기이고, R1~R3, R5, R6, R8, R9, R12 , R13, R16~R39은 모두 수소인 화합물;상기 화학식 1에서 상기 R4, R6, R8, R10, R12 및 R14는 모두 메틸기이고, R1~R3, R5, R7, R9, R11, R13 , R15~R39은 모두 수소인 화합물;상기 화학식 1에서 R1~ R39은 모두 수소인 화합물; 및상기 화학식 1에서, R4, R6, R8, R10, R12, R 14, R18, R21, R26, R29, R34, R 37은 모두 메틸기이고, R1~R3, R5, R7, R9, R11 , R13, R15~R17, R19, R20, R22 ~R25, R27, R28, R30~R33, R35, R36, R38, R39은 모두 수소인 화합물;로 이루어진 군으로부터 선택되는 것을 특징으로 하는 카바졸 함유 화합물.
- 제1항에 있어서, 상기 화합물이 하기 화학식 8로 표시되는 화합물인 것을 특징으로 하는 카바졸 함유 화합물.[화학식 8]
- 한 쌍의 전극 사이에 구비되어 있는 유기막을 포함하고 있는 유기 전계 발광 소자에 있어서,상기 유기막이 제1항 내지 제3항중 어느 한 항의 카바졸 함유 화합물을 포함하고 있는 것을 특징으로 하는 유기 전계 발광 소자.
- 제4항에 있어서, 상기 유기막이 발광층인 것을 특징으로 하는 유기 전계 발광 소자.
- 제4항에 있어서, 상기 발광층이 가시영역의 인광 또는 형광 도펀트를 더 포함하는 것을 특징으로 하는 유기 전계 발광 소자.
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KR10-2003-0075803A KR100537620B1 (ko) | 2003-10-29 | 2003-10-29 | 카바졸 함유 화합물 및 이를 이용한 유기 전계 발광 소자 |
JP2004224694A JP4133955B2 (ja) | 2003-10-29 | 2004-07-30 | カルバゾール含有化合物及びそれを利用した有機電界発光素子 |
US10/976,231 US20050175858A1 (en) | 2003-10-29 | 2004-10-29 | Carbazole containing compound and organic electroluminescent display device using the same |
CNB2004100877611A CN100422176C (zh) | 2003-10-29 | 2004-10-29 | 含咔唑化合物以及使用该化合物的有机电致发光显示装置 |
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Publication number | Priority date | Publication date | Assignee | Title |
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WO2003080761A1 (fr) * | 2002-03-25 | 2003-10-02 | Idemitsu Kosan Co., Ltd. | Materiau pour element organique electroluminescent et element organique electroluminescent l'utilisant |
KR100556422B1 (ko) * | 2004-04-19 | 2006-03-03 | 엘지전자 주식회사 | 청색 인광용 유기 전계 발광 소자 |
JP4214482B2 (ja) * | 2004-08-26 | 2009-01-28 | 独立行政法人科学技術振興機構 | 有機エレクトロルミネッセンス素子 |
GB2439030B (en) * | 2005-04-18 | 2011-03-02 | Konica Minolta Holdings Inc | Organic electroluminescent device, display and illuminating device |
JP4794918B2 (ja) * | 2005-06-20 | 2011-10-19 | 富士フイルム株式会社 | 有機電界発光素子 |
JP2007001895A (ja) * | 2005-06-22 | 2007-01-11 | Tosoh Corp | 燐光ホスト化合物及びそれを用いた有機電界発光素子 |
TWI400222B (zh) | 2005-11-03 | 2013-07-01 | Semiconductor Energy Lab | 二苯乙烯衍生物,發光元件用之材料,發光元件,發光裝置,及電子設備 |
KR101511788B1 (ko) * | 2005-12-12 | 2015-04-13 | 호도가야 가가쿠 고교 가부시키가이샤 | m-카르바졸릴페닐기를 함유하는 화합물 |
JP5105820B2 (ja) * | 2006-10-12 | 2012-12-26 | 国立大学法人九州大学 | カルバゾール誘導体及びこれを用いた有機固体レーザー材料 |
KR100795817B1 (ko) | 2007-02-20 | 2008-01-21 | 삼성에스디아이 주식회사 | 유기 발광 소자, 이의 제조 방법 및 유기층 형성 방법 |
JP2008243557A (ja) * | 2007-03-27 | 2008-10-09 | Osaka Univ | 有機エレクトロルミネッセンス素子及びその製造方法 |
KR100829761B1 (ko) | 2007-05-16 | 2008-05-15 | 삼성에스디아이 주식회사 | 유기 발광 소자 |
KR100858824B1 (ko) | 2007-05-31 | 2008-09-17 | 삼성에스디아이 주식회사 | 유기 발광 소자 및 이의 제조 방법 |
KR100922758B1 (ko) | 2008-02-20 | 2009-10-21 | 삼성모바일디스플레이주식회사 | 유기 발광 소자 |
KR100922761B1 (ko) * | 2008-03-04 | 2009-10-21 | 삼성모바일디스플레이주식회사 | 유기 발광 소자 |
KR20110061916A (ko) * | 2009-12-02 | 2011-06-10 | 삼성모바일디스플레이주식회사 | 전면 발광형 유기 발광 소자 |
DE102010005697A1 (de) * | 2010-01-25 | 2011-07-28 | Merck Patent GmbH, 64293 | Verbindungen für elektronische Vorrichtungen |
JP5662994B2 (ja) | 2010-02-26 | 2015-02-04 | 新日鉄住金化学株式会社 | 有機電界発光素子 |
KR101443700B1 (ko) * | 2011-07-13 | 2014-09-30 | 율촌화학 주식회사 | 청색 인광용 호스트 물질, 이를 포함하는 유기 박막 및 유기 발광 소자 |
CN103907217B (zh) | 2011-09-12 | 2016-10-12 | 新日铁住金化学株式会社 | 有机电致发光元件 |
WO2013096921A1 (en) * | 2011-12-22 | 2013-06-27 | Georgia Tech Research Corporation | Non-crosslinked polystyrene triscarbazole hole transport materials |
KR102541267B1 (ko) | 2015-10-05 | 2023-06-12 | 삼성전자주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
CN110446703A (zh) * | 2017-03-29 | 2019-11-12 | 默克专利有限公司 | 芳族化合物 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH10316658A (ja) * | 1997-05-21 | 1998-12-02 | Mitsubishi Chem Corp | 4,4’−ビス(n−カルバゾリル)ジフェニルアミン誘導体及びそれを用いた有機電界発光素子 |
JP2000063335A (ja) * | 1998-08-17 | 2000-02-29 | Minolta Co Ltd | 新規アミノ化合物、その製造法及び用途 |
KR20020026866A (ko) * | 2000-03-27 | 2002-04-12 | 도미나가 가즈토 | 유기 전자발광 소자 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH10168443A (ja) * | 1996-12-17 | 1998-06-23 | Sanyo Shinku Kogyo Kk | 有機発光素子の正孔または電子輸送層等に用いられるフェニルカルバゾール誘導体 |
JP3447945B2 (ja) * | 1998-02-26 | 2003-09-16 | 沖電気工業株式会社 | 発光材料およびこれを用いた有機el素子 |
WO2003080761A1 (fr) * | 2002-03-25 | 2003-10-02 | Idemitsu Kosan Co., Ltd. | Materiau pour element organique electroluminescent et element organique electroluminescent l'utilisant |
US6562982B1 (en) * | 2002-07-25 | 2003-05-13 | Xerox Corporation | Carbazole compounds |
-
2003
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH10316658A (ja) * | 1997-05-21 | 1998-12-02 | Mitsubishi Chem Corp | 4,4’−ビス(n−カルバゾリル)ジフェニルアミン誘導体及びそれを用いた有機電界発光素子 |
JP2000063335A (ja) * | 1998-08-17 | 2000-02-29 | Minolta Co Ltd | 新規アミノ化合物、その製造法及び用途 |
KR20020026866A (ko) * | 2000-03-27 | 2002-04-12 | 도미나가 가즈토 | 유기 전자발광 소자 |
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CN1623990A (zh) | 2005-06-08 |
US20050175858A1 (en) | 2005-08-11 |
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