KR20090129799A - 신규한 카바졸 유도체 및 이를 포함하는 유기 전계발광소자 - Google Patents
신규한 카바졸 유도체 및 이를 포함하는 유기 전계발광소자 Download PDFInfo
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- KR20090129799A KR20090129799A KR1020080055897A KR20080055897A KR20090129799A KR 20090129799 A KR20090129799 A KR 20090129799A KR 1020080055897 A KR1020080055897 A KR 1020080055897A KR 20080055897 A KR20080055897 A KR 20080055897A KR 20090129799 A KR20090129799 A KR 20090129799A
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- organic electroluminescent
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- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title claims abstract 4
- 238000002347 injection Methods 0.000 claims abstract description 62
- 239000007924 injection Substances 0.000 claims abstract description 62
- 239000000463 material Substances 0.000 claims abstract description 44
- 230000005525 hole transport Effects 0.000 claims abstract description 41
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 239000007983 Tris buffer Substances 0.000 claims abstract description 10
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 10
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000002019 doping agent Substances 0.000 claims abstract description 9
- 239000000126 substance Substances 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 230000000903 blocking effect Effects 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 229910052698 phosphorus Inorganic materials 0.000 claims description 12
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 229910052710 silicon Inorganic materials 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229940125904 compound 1 Drugs 0.000 claims description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 229910018068 Li 2 O Inorganic materials 0.000 claims description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 11
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- -1 carbazole derivative compound Chemical class 0.000 abstract description 5
- 239000010410 layer Substances 0.000 description 126
- 150000001716 carbazoles Chemical class 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 238000002207 thermal evaporation Methods 0.000 description 6
- MSDMPJCOOXURQD-UHFFFAOYSA-N C545T Chemical compound C1=CC=C2SC(C3=CC=4C=C5C6=C(C=4OC3=O)C(C)(C)CCN6CCC5(C)C)=NC2=C1 MSDMPJCOOXURQD-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 238000000434 field desorption mass spectrometry Methods 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 2
- 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 2
- MDXCDMSVFQIDGN-UHFFFAOYSA-N 2,7-dibromo-9-phenylcarbazole Chemical compound C=1C(Br)=CC=C(C2=CC=C(Br)C=C22)C=1N2C1=CC=CC=C1 MDXCDMSVFQIDGN-UHFFFAOYSA-N 0.000 description 2
- 0 C*=C*=C[C@]1C=C(*)N(*)[C@@]2C(*)=C(C)C(*)=CC12 Chemical compound C*=C*=C[C@]1C=C(*)N(*)[C@@]2C(*)=C(C)C(*)=CC12 0.000 description 2
- 108010043121 Green Fluorescent Proteins Proteins 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229940125877 compound 31 Drugs 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001194 electroluminescence spectrum Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000004519 manufacturing process Methods 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
- 239000012044 organic layer Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YMRHXVOHLPIMNN-UHFFFAOYSA-N 1-n-(3-methylphenyl)-2-n,2-n-diphenylbenzene-1,2-diamine Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 YMRHXVOHLPIMNN-UHFFFAOYSA-N 0.000 description 1
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
- SOODLDGRGXOSTA-UHFFFAOYSA-N 2-bromo-9-phenylcarbazole Chemical compound C=1C(Br)=CC=C(C2=CC=CC=C22)C=1N2C1=CC=CC=C1 SOODLDGRGXOSTA-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
- XSUNFLLNZQIJJG-UHFFFAOYSA-N 2-n-naphthalen-2-yl-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C=C2C=CC=CC2=CC=1)C1=CC=CC=C1 XSUNFLLNZQIJJG-UHFFFAOYSA-N 0.000 description 1
- MBPCKEZNJVJYTC-UHFFFAOYSA-N 4-[4-(n-phenylanilino)phenyl]aniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 MBPCKEZNJVJYTC-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
- 229910001148 Al-Li alloy Inorganic materials 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- AWFDUOVDQHJMKG-UHFFFAOYSA-N N-(3-methylphenyl)-2-phenoxyaniline Chemical compound CC=1C=C(C=CC=1)NC1=C(C=CC=C1)OC1=CC=CC=C1 AWFDUOVDQHJMKG-UHFFFAOYSA-N 0.000 description 1
- NUGPIZCTELGDOS-QHCPKHFHSA-N N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclopentanecarboxamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CC[C@@H](C=1C=NC=CC=1)NC(=O)C1CCCC1)C NUGPIZCTELGDOS-QHCPKHFHSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- CKUAXEQHGKSLHN-UHFFFAOYSA-N [C].[N] Chemical compound [C].[N] CKUAXEQHGKSLHN-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000006254 arylation reaction Methods 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 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
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 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
- 238000005259 measurement Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- DUJHBLBNMJIXGF-UHFFFAOYSA-N n-naphthalen-1-yl-9-phenylcarbazol-3-amine Chemical compound C=1C=CC2=CC=CC=C2C=1NC(C=C1C2=CC=CC=C22)=CC=C1N2C1=CC=CC=C1 DUJHBLBNMJIXGF-UHFFFAOYSA-N 0.000 description 1
- 239000007773 negative electrode material Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002904 solvent Substances 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
- 230000007704 transition Effects 0.000 description 1
- 238000007740 vapor deposition 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
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-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
정공주입층 및 정공수송층 물질 | 구동전압 (V) | 전류 밀도 (mA/㎠) | 효율 (cd/A) | CIE xy |
화합물 1 | 7.62 | 14.87 | 26.84 | (0.281, 0.649) |
화합물 9 | 7.69 | 15.31 | 26.07 | (0.299, 0.641) |
화합물 31 | 8.53 | 15.80 | 25.23 | (0.291, 0.640) |
2T-NATA | 8.54 | 15.90 | 25.16 | (0.318, 0.623) |
4000nit에서 측정함 |
Claims (14)
- 하기 화학식 1로 표시되는 카바졸 유도체인 화합물:화학식 1상기 화학식 1에서,Ar1 및 Ar2는 각각 독립적으로 S, N, O, P 및 Si 중 하나 이상의 헤테로 원자를 함유하거나 함유하지 않는 C1-30 알킬기에 의해 치환되거나 비치환된 C6-30 아릴기, 또는 S, N, O, P 및 Si 중 하나 이상의 헤테로 원자를 함유하는 C6-30 아릴기이고,R1 내지 R9는 각각 독립적으로 수소 원자; 할로겐, 시아노기, 하이드록시기, 티올기 또는 알콕시기에 의해 치환되거나 비치환된 C1-30 알킬기 또는 C6-30 아릴기; 또는 S, N, O, P 및 Si 중 하나 이상의 헤테로 원자를 함유하는 C1-30 알킬기 또는 C6-30 아릴기이고,임의적으로 R1 내지 R9 중에서 선택된 2개 이상은 서로 결합하여 고리를 형성할 수 있다.
- 제 1 항에 있어서,Ar1, Ar2, R1, R2 및 R9이 각각 독립적으로 알킬로 치환되거나 비치환된, 페닐, 나프틸, 페난트렌일, 또는 플루오렌일인 화합물.
- 하기 화학식 2로 표시되는 화합물:화학식 2상기 화학식 2에서,Ar3는 각각 독립적으로 S, N, O, P 및 Si 중 하나 이상의 헤테로 원자를 함유하거나 함유하지 않는 C1-30 알킬기에 의해 치환되거나 비치환된 C6-30 아릴기, 또는 S, N, O, P 및 Si 중 하나 이상의 헤테로 원자를 함유하는 C6 -30 아릴기이고,R10 내지 R17는 각각 독립적으로 수소 원자; 할로겐, 시아노기, 하이드록시기, 티올기 또는 알콕시기에 의해 치환되거나 비치환된 C1 -30 알킬기 또는 C6 -30 아릴기; S, N, O, P 및 Si 중 하나 이상의 헤테로 원자를 함유하는 C1 -30 알킬기 또는 C6 -30 아릴기이고,임의적으로 R10 내지 R17 중에서 선택된 2개 이상은 서로 결합하여 고리를 형성할 수 있다.
- 제 5 항에 있어서,Ar3, R10 및 R17이 각각 독립적으로 알킬로 치환되거나 비치환된, 페닐, 나프틸, 페난트렌일, 또는 플루오렌일인 화합물.
- 양극, 음극 및 두 전극 사이에 발광층 및 정공주입층 및 정공수송층 중 하나 이상을 포함하는 유기 전계발광 소자로서,상기 정공주입층 및 정공수송층 중 선택된 하나 이상의 층이 제 1 항 내지 제 7 항 중 어느 한 항에 따른 화합물을 포함하는 유기 전계발광 소자.
- 제 9 항에 있어서,양극, 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 및 음극이 순차적으로 적층된 구조를 갖는 것을 특징으로 하는 유기 전계발광 소자.
- 제 10 항에 있어서,상기 발광층이, 발광 호스트 물질로서 트리스(8-하이드록시퀴놀리놀라토) 알루미늄, 을 포함하고, 형광 또는 인광 도펀트를 포함하는 유기 전계발광 소자.
- 제 10 항에 있어서,상기 전자수송층이 트리스(8-하이드록시퀴놀리놀라토)알루미늄(Alq3)을 포함하는 유기 전계발광 소자.
- 제 10 항에 있어서,상기 발광층과 전자수송층 사이에 정공차단층을 추가로 포함하고, 상기 정공차단층이 (8-하이드록시퀴놀리놀라토)리튬(Liq), 비스(8-하이드록시-2-메틸퀴놀리놀나토)-알루미늄 비페녹사이드(BAlq), 바쏘쿠프로인(bathocuproine, BCP) 및 LiF 중에서 선택된 하나 이상을 포함하는 유기 전계발광 소자.
- 제 10 항에 있어서,상기 전자주입층 물질이 LiF, Liq, Li2O, BaO, NaCl 및 CsF 중에서 선택된 하나 이상을 포함하는 유기 전계발광 소자.
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