TW201305313A - 用於有機電子材料之新穎化合物及使用該化合物之有機電場發光裝置 - Google Patents
用於有機電子材料之新穎化合物及使用該化合物之有機電場發光裝置 Download PDFInfo
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- TW201305313A TW201305313A TW101120632A TW101120632A TW201305313A TW 201305313 A TW201305313 A TW 201305313A TW 101120632 A TW101120632 A TW 101120632A TW 101120632 A TW101120632 A TW 101120632A TW 201305313 A TW201305313 A TW 201305313A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 90
- 239000012776 electronic material Substances 0.000 title description 7
- 125000003118 aryl group Chemical group 0.000 claims description 65
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 45
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 230000005684 electric field Effects 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 24
- -1 cyano, oxazolyl Chemical group 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 125000002950 monocyclic group Chemical group 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 12
- 125000001931 aliphatic group Chemical group 0.000 claims description 12
- 229910052805 deuterium Inorganic materials 0.000 claims description 12
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 12
- 125000003367 polycyclic group Chemical group 0.000 claims description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 125000001769 aryl amino group Chemical group 0.000 claims description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 239000007983 Tris buffer Substances 0.000 claims description 7
- 229910052796 boron Inorganic materials 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 3
- 125000003003 spiro group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 125000005717 substituted cycloalkylene group Chemical group 0.000 claims description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 9
- 238000002425 crystallisation Methods 0.000 abstract description 2
- 230000008025 crystallization Effects 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- 239000011541 reaction mixture Substances 0.000 description 35
- 239000000463 material Substances 0.000 description 34
- 239000010410 layer Substances 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 235000019439 ethyl acetate Nutrition 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000002019 doping agent Substances 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000012153 distilled water Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 238000007740 vapor deposition Methods 0.000 description 5
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group 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 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- MZSAMHOCTRNOIZ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylaniline Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(NC2=CC=CC=C2)C=CC=1 MZSAMHOCTRNOIZ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 3
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 description 3
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 3
- 125000003943 azolyl group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 3
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 2
- 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 2
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 2
- TUQSVSYUEBNNKQ-UHFFFAOYSA-N 2,4-dichloroquinazoline Chemical compound C1=CC=CC2=NC(Cl)=NC(Cl)=C21 TUQSVSYUEBNNKQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- HAEQAUJYNHQVHV-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylbenzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 HAEQAUJYNHQVHV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- REAYFGLASQTHKB-UHFFFAOYSA-N [2-[3-(1H-pyrazol-4-yl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound N1N=CC(=C1)C=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 REAYFGLASQTHKB-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 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 description 2
- 239000001273 butane Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000004770 chalcogenides Chemical class 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 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 2
- 238000000151 deposition Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
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- 239000002904 solvent Substances 0.000 description 2
- 239000002344 surface layer Substances 0.000 description 2
- QBLFZIBJXUQVRF-UHFFFAOYSA-N (4-bromophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Br)C=C1 QBLFZIBJXUQVRF-UHFFFAOYSA-N 0.000 description 1
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
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- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
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- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
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- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
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- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
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- 230000000052 comparative effect Effects 0.000 description 1
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- ZXHUJRZYLRVVNP-UHFFFAOYSA-N dibenzofuran-4-ylboronic acid Chemical compound C12=CC=CC=C2OC2=C1C=CC=C2B(O)O ZXHUJRZYLRVVNP-UHFFFAOYSA-N 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 125000000524 functional group Chemical group 0.000 description 1
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- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
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- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
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- 229910052741 iridium Inorganic materials 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
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- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SIWVEOZUMHYXCS-UHFFFAOYSA-N oxo(oxoyttriooxy)yttrium Chemical compound O=[Y]O[Y]=O SIWVEOZUMHYXCS-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001151 peptidyl group Chemical group 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- KNXKVYCVGXFLES-UHFFFAOYSA-N pyridine-2-carboximidamide Chemical compound NC(=N)C1=CC=CC=N1 KNXKVYCVGXFLES-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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Abstract
本發明關於新穎化合物及含有該化合物之有機電場發光裝置。因根據本發明之化合物在傳導電子具有高效率,當製造裝置時可避免結晶。更進一步地,該化合物有好的層成形性並可增進該裝置之電流特性。因此,他們可製造一擁有減低的驅動電壓與增強的功率效率之有機電場發光裝置。
Description
本發明關於用於有機電子材料之新穎化合物及使用該化合物之有機電場發光裝置。
電場發光(electroluminescent,EL)裝置係一自發光裝置,它可提供較寬視角、較傑出之對比度及較快響應速度而優於其他種類的顯示裝置。伊斯門-柯達(Eastman Kodak)首先研發了一有機電場發光裝置,藉由使用小分子為芳香族二胺及鋁錯合物作為形成發光層之物質。[Appl.Phys.Lett.51,913,1987]
決定有機電場發光裝置的發光效率的最重要因素係發光材料。到目前為止,螢光材料被廣泛地使用作為發光材料。然而,就電場發光機制而言,磷光材料理論上比螢光材料呈現出高於四倍的發光效率。因此,最近磷光材料已被探討。三價銥化合物已被廣泛使用作為磷光材料,包含分別作為紅光、綠光及藍光材料之雙(2-(2’-苯并噻吩基)-吡啶-N,C3’)銥(乙醯丙酮)[(acac)Ir(btp)2]、参(2-苯基吡啶)銥[Ir(ppy)3]、雙(4,6-二氟苯基吡啶-N,C2’)吡啶甲醯銥(Firpic)。尤其最近日本、歐洲與美國致力於研發許多磷光材料。
目前4,4’-N,N’-二咔唑-聯苯(CBP)是最廣泛已知主體材料之磷光物質。進一步地,已知使用浴銅靈(bathocuproine(BCP))與鋁(III)雙(2-甲基-8-羥基喹
啉)(4-苯基酚)(BAlq)作為電洞阻隔層的有機電場發光裝置具有高效率,以及Pioneer等(日本)用BAlq作為主體材料以研發高性能的有機電場發光裝置。
雖然這些磷主體材料提供好的發光特性,但有下述缺點:
1.由於它們的玻璃轉換溫度低與熱穩定性差,在真空高溫沉積過程中它們可能發生降解。
2.有機電場發光裝置的電能效率(power efficiency)可由[(π/電壓)×功率效率]而得,電能效率與電壓成反比,因此,為了減少電能消耗,電能效率應該提高。當使用常用的材料,例如Balq或CBP作為磷光主體材料時,雖然包含磷光材料之有機電場發光裝置具有高於包含螢光材料者的功率效率(燭光/安培(cd/A)),但相較於使用螢光材料的有機電場發光裝置必須有明顯的高驅動電壓。因此在電能效率(流明/瓦(lm/W))上沒有優勢。
3.更進一步地,有機電場發光裝置的操作壽命短且發光效率仍待改進。
在國際專利公開WO 2006/049013號中,揭露以縮合雙環基團為主鏈結構之化合物作為有機電場發光材料。然而,其中並未揭露一稠合咔唑化合物,該化合物經以經芳環稠合的雜環烷基或環烷基取代之含氮縮合雙環基予以取代。
本發明的目的係提供一用於有機電子材料之化合物,該化合物具有優良的結構以賦予裝置高的發光效率與長的操作壽命,並擁有適當色座標;以及使用該化合物擁有高效率與長壽命之有機電場發光裝置。
本發明者發現上述目的可由下述式1代表之化合物達成:
其中,L1與L2各獨立表示單鍵、經取代或未經取代之3員至30員伸雜芳基、經取代或未經取代之(C6-C30)伸芳基、經取代或未經取代之(C6-C30)伸環烷基;X1係表示CH或N;Y1至Y3各獨立表示-O-、-S-、-CR6R7-或-NR8-,限制條件為Y2和Y3不會同時存在;R1至R5各獨立表示氫、氘、鹵素、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之3員至30員雜芳基、經取代或未經取代之(C3-C30)環烷基、經取代或未經取代之5員至7員雜環
烷基、經取代或未經取代之(C6-C30)芳基(C1-C30)烷基、-NR11R12、-SiR13R14R15、-SR16、-OR17、氰基、硝基或羥基;或R1至R5各獨立連結至一個或多個相鄰取代基而形成其中一個或多個碳原子可被至少一個選自氮、氧和硫之雜原子置換之單環或多環之(C5-C30)脂族環或芳環;R6至R8和R11至R17各獨立代表氫、氘、鹵素、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之3員至30員雜芳基、經取代或未經取代之5員至7員雜環烷基、或經取代或未經取代之(C3-C30)環烷基;或R6至R8和R11至R17獨立各連結至一個或多個相鄰取代基而形成其中一個或多個碳原子可被至少一個選自氮、氧和硫之雜原子置換之單環或多環之(C5-C30)脂族環或芳環;a、b、c和e各獨立表示整數1至4;當a、b、c或e係2或更大整數時,各R1、各R2、各R3或各R5係相同或不同;d係表示整數1至3;當d係2或更大整數時,各R4係相同或不同;以及該雜環烷基和(伸)雜芳基含有至少一個選自B、N、O、S、P(=O)、Si及P之雜原子。
根據本發明之有機電子材料化合物可製造一高發光效率和長操作壽命之有機電場發光裝置。
此外,因根據本發明之化合物在傳導電子具有高效
率,當製造裝置時可避免結晶。更進一步地,該化合物具有好的層成形性並可改良該裝置之電流特性。因此,他們可製造一擁有減低的驅動電壓與增強的功率效率之有機電場發光裝置。
本發明詳述如下。然而,以下描述意圖解釋本發明,非意圖以任何方式限制發明範圍於此。
本發明係有關一由上述式1表示之有機電子材料化合物,以及含有此化合物之有機電場發光裝置。
此處,「(C1-C30)(伸)烷基」意即一具有1個至30個碳原子之且鏈型或支鏈型(伸)烷基,其中該碳原子數較佳係1個至20個,更佳係1個至10個,並包含甲基、乙基、正丙基、異丙基、正丁基、異丁基、第三丁基等,但不受限於此;「(C2-C30)(伸)烯基」意即一具有2個至30個碳原子之直鏈型或支鏈型(伸)烯基,其中該碳原子數較佳係2個至20個,更佳係2個至10個,並包含乙烯基、1-丙烯基、2-丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、2-甲基丁-2-烯基等,但不受限於此;「(C2-C30)炔基」意即一具有2個至30個碳原子之直鏈型或支鏈型炔基,其中該碳原子數較佳係2個至20個,更佳係2個至10個,並包含乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基戊-2-炔基等,但不受限於此;「(C1-C30)烷氧基」意即一具有1個至30個碳原子之直鏈型或支鏈型烷氧基,其中該碳原子數較佳係1個至20個,更佳係1
個至10個,並包含甲氧基、乙氧基、丙氧基、異丙氧基、1-乙基丙氧基等,但不受限於此;「(C3-C30)環烷基」意即一具有3個至30個碳原子之單環或多環烴基,其中該碳原子數較佳係3個至20個,更佳係3個至7個,並包含環丙基、環丁基、環戊基、環己基等,但不受限於此;「(C6-C30)伸環烷基」係由環烷基移除一個氫者,具有6個至30個碳原子,較佳係6個至20個碳原子,更佳係6或7個碳原子;「5員至7員雜環烷基」係一環烷基包含至少一個選自B、N、O、S、P(=O)、Si和P之雜原子,較佳係N、O和S、以及5環至7環主鏈原子,並包含四氫呋喃、吡咯啶、四氫噻吩、四氫吡喃等,但不受限於此;「(C6-C30)(伸)芳基」係來自芳烴之單環或稠合環基,具有6個至30個碳原子,較佳係6個至20個碳原子,更佳係6個至12個碳原子,並包含苯基、聯苯基、聯三苯基(terpheny)、萘基、茀基、菲基、蒽基、二氫茚基、茚基、聯伸三苯基(triphenylenyl)、芘基、并四苯基、苝基、蒯基(chrysenyl)、稠四苯基、丙二烯合茀基(fluoranthenyl)等,但不受限於此;「3員至30員(伸)雜芳基」係包含至少一個選自B、N、O、S、P(=O)、Si和P之雜原子(較佳係包含1至4個雜原子)以及3環至30環主鏈原子之芳基;其係單環或與至少一個苯環縮合之稠合環;較佳係具有5至21個環主鏈原子,更佳係具有5至12個環主鏈原子;可為部分飽和;可為以一個或多個單鍵連結至少一個雜芳基或芳基至雜芳基所形成者;以及包含單環形態雜芳基,
含呋喃基、噻吩基、吡咯基、咪唑基、吡唑基、噻唑基、噻二唑基、異噻唑基、異唑基、唑基、二唑基、三基、四基、三唑基、四唑基、呋呫基、吡啶基、吡基、嘧啶基、嗒基等;稠合環形態雜芳基,包含苯并呋喃基、苯并噻吩基、異苯并呋喃基、二苯并呋喃基、二苯并噻吩基、苯并咪唑基、苯并噻唑基、苯并異噻唑基、苯并異唑基、苯并唑基、異吲哚基、吲哚基、吲唑基、苯并噻二唑基、喹啉基、異喹啉基、噌啉基(cinnolinyl)、喹唑啉基、喹啉基、咔唑基、啡基、啡啶基、苯并二呃基(benzodioxolyl)等,但不受限於此。此外,「鹵素」包含F、Cl、Br和I。
其中,在「經取代或未經取代之」表達中之「經取代」意指特定官能基之氫原子被另一原子或基團(例如,取代基)所取代。
在L1、L2、R1至R5、R6至R8和R11至R17基中之該經取代之(伸)烷基、經取代之烯基、經取代之炔基、經取代之伸環烷基、經取代之環烷基、經取代之雜環烷基、經取代之(伸)芳基、經取代之(伸)雜芳基和經取代之芳環之取代基,各獨立較佳係至少一個選自下列所組成群組者:氘、鹵素、經鹵素取代或未經取代之(C1-C30)烷基、(C6-C30)芳基、經(C1-C30)烷基或(C6-C30)芳基取代或未經取代之3員至30員雜芳基、(C3-C30)環烷基、3員至7員雜環烷基、三(C1-C30)烷基矽基、三(C6-C30)芳基矽基、二(C1-C30)烷基(C6-C30)芳基矽基、(C1-C30)烷基二(C6-C30)芳基矽
基、(C2-C30)烯基、(C2-C30)炔基、氰基、咔唑基、二(C1-C30)烷基胺基、經(C1-C30)烷基取代或未經取代之二(C6-C30)芳基胺基、(C1-C30)烷基(C6-C30)芳基胺基、二(C6-C30)芳硼羰基、二(C1-C30)烷硼羰基、(C1-C30)烷基(C6-C30)芳硼羰基、(C6-C30)芳基(C1-C30)烷基、(C1-C30)烷基(C6-C30)芳基、羧基、硝基和羥基,更佳係至少一個選自下列所組成群組者:氘、鹵素、經鹵素取代或未經取代之(C1-C30)烷基、(C6-C30)芳基、(C1-C30)烷基(C6-C30)芳基、經(C1-C30)烷基或(C6-C30)芳基取代或未經取代之3員至30員雜芳基、(C3-C30)環烷基、三(C6-C30)芳基矽基、經(C1-C30)烷基取代或未經取代之二(C6-C30)芳基胺基、和(C6-C30)芳基(C1-C30)烷基,甚至更佳係至少一個選自下列所組成群組者:氘、氟、甲基、苯基、萘基、聯苯基、三苯矽基、經第三丁基取代之二苯基胺基、經第三丁基取代之咔唑基。
在上述式1中,L1和L2各獨立較佳係單鍵、經(C1-C6)烷基取代或未經取代之(C6-C20)伸芳基或未經取代之(C6-C30)伸環烷基,更佳係單鍵、伸苯基、伸聯苯基、二甲基伸苯基或伸環己基。
在上述式1中,Y1至Y3各獨立表示-O-、-S-、-CR6R7-或-NR8-,其中,R6至R8各獨立較佳係氫、氘、鹵素、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之3員至30員雜芳基;或R6至R8各獨立連結至一個或多個相鄰取代基而形成其中
一個或多個碳原子可被至少一個選自氮、氧和硫之雜原子置換之單環或多環之(C5-C30)脂族環或芳環;更佳係(C1-C6)烷基、經氘取代或未經取代之(C6-C20)芳基、鹵素、(C1-C6)烷基、(C6-C12)芳基、三(C6-C12)芳基矽基、經(C1-C6)烷基取代之二(C6-C12)芳基胺基或經(C1-C6)烷基取代之5員至21員雜芳基;經(C6-C12)芳基取代或未經取代之5員至21員雜芳基;或R6至R8各獨立連結至一個或多個相鄰取代基而形成其中一個或多個碳原子可被至少一個選自氮、氧和硫之雜原子置換之單環或多環之(C5-C30)脂族環或芳環;甚至更佳係甲基、苯基、聯苯基、聯三苯基、萘基、萘基苯基、經氘取代之苯基、經氟取代之苯基、經甲基取代之苯基、經三苯基矽基取代之苯基、經(經第三丁基取代之二苯基胺基)取代之苯基、經(經第三丁基取代之咔唑基)取代之苯基、經甲基取代之茀基、經苯基取代之咔唑基;或R6至R8各獨立連結至一個或多個相鄰取代基而形成單環或多環之(C5-C30)脂族環或芳環。
在上述式1中,R1至R5各獨立較佳係氫、氘、鹵素、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之3員至30員雜芳基、N-咔唑基、-NR11R12或-SiR13R14R15;或R1至R5各獨立連結至一個或多個相鄰取代基而形成其中一個或多個碳原子可被至少一個選自氮、氧和硫之雜原子置換之單環或多環之(C5-C30)脂族環或芳環,其中R11至R15各獨立較佳係經取代或未經取代之(C1-C30)烷基、經取代或未經取代之
(C6-C30)芳基、或經取代或未經取代之3員至30員雜芳基,更佳係未經取代之(C1-C6)烷基、未經取代之(C6-C12)芳基、未經取代之5員至21員雜芳基,甚至更佳係甲基、苯基或咔唑基。
在上述式1中,R1至R5各獨立更佳係未經取代之(C6-C20)芳基、未經取代之5員至21員雜芳基、-NR11R12或-SiR13R14R15;或R1至R5各獨立連結至一個或多個相鄰取代基而形成單環或多環之(C5-C30)脂族環或芳環;甚至更佳係苯基、咔唑基、二苯基胺或甲基二苯基矽基;或R1至R5各獨立連結至一個或多個相鄰取代基而形成單環或多環之(C5-C30)脂族環或芳環。
在上述式1中,係選自以下結構,但不
受限於此:
本發明之代表性化合物包含下述化合物,但不受限於此:
關於本發明之有機電子材料化合物可根據以下反應式製備:
[反應式2]
其中R1至R5、Y1至Y3、X1、L1、L2、a、b、c、d和e如上述式1定義,X代表鹵素。
此外,本發明提供包括式1化合物之有機電場發光裝置。該有機電場發光裝置包括第一電極、第二電極以及至少一層插置於該第一電極與該第二電極間之有機層。該有機層包括至少一種本發明之式1化合物。進一步地,該有機層包括發光層,其中係包含本發明之式1化合物作為主體材料。
此外,與本發明之主體材料一起用於有機電場發光裝置中的磷光摻雜劑,可選自下述式2表示之化合物:式2 M1 L101 L102 L103
其中M1係選自由Ir、Pt、Pd和Os所組成之群組;L101、L102和L103係各獨立選自以下結構:
R201至R203各獨立表示氫、氘、經一個或多個鹵素取代或未經取代之(C1-C30)烷基、經一個或多個(C1-C30)烷基取代或未經取代之(C6-C30)芳基、或鹵素;R204至R219各獨立表示氫、氘、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C1-C30)烷氧基、經取代或未經取代之(C3-C30)環烷基、經取代或未經取代之(C2-C30)烯基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之單或二(C1-C30)烷基胺基、經取代或未經取代之單或二(C6-C30)芳基胺基、SF5、經取代或未經取代之三(C1-C30)烷基矽基、經取代或未經取代之二(C1-C30)
烷基(C6-C30)芳基矽基、經取代或未經取代之三(C6-C30)芳基矽基、氰基或鹵素;R220至R223各獨立表示氫、氘、經一個或多個鹵素取代或未經取代之(C1-C30)烷基、或經一個或多個(C1-C30)烷基取代或未經取代之(C6-C30)芳基;R224和R225各獨立表示氫、氘、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基或鹵素;或R224和R225可經由具有或不具有稠合環之(C3-C12)伸烷基或(C3-C12)伸烯基相互連結而形成單環或多環之脂族環或芳環;R226係表示經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之5員至30員雜芳基或鹵素;R227至R229各獨立表示氫、氘、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基或鹵素;Q係表示、或;R231至R242各獨立表示氫、氘、經一個或多個鹵素取代或未經取代之(C1-C30)烷基、(C1-C30)烷氧基、鹵素、經取代或未經取代之(C6-C30)芳基、氰基、經取代或未經取代之(C5-C30)環烷基,或每個R231至R242可經由(C2-C30)伸烷基或(C2-C30)伸烯基連結至相鄰取代基而形成螺環或稠合環,或可經由(C2-C30)伸烷基或(C2-C30)伸烯基連結至R207或R208以形成飽和或不飽和稠合環。
式2之摻雜劑包含下述化合物,但不受限於此:
本發明之有機電場發光裝置,除了包括式1化合物外,可進一步包括至少一種選自芳香胺系或苯乙烯芳基胺系之化合物。
於本發明之有機電場發光裝置中,該有機層可進一步包括至少一種選自週期表之第1族金屬、第2族金屬、第4週期過渡金屬、第5週期過渡金屬、鑭系金屬及d-過渡元素的有機金屬所組成群組之金屬,或至少一種含有上述金屬之錯合物。該有機層可包括發光層及電荷產生層。
此外,除了包括本發明之化合物外,該有機電場發光裝置可藉由進一步包括至少一層包括藍光電場發光化合物、紅光電場發光化合物或綠光電場發光化合物之發光層而發射白光。
較佳地,於本發明之有機電場發光裝置中,係將選自硫屬化合物(chalcogenide)層、金屬鹵化物層及金屬氧化物層之至少一層層體(後文中稱為「表面層」)設置於一個或兩個電極的一個或多個內表面上。更具體而言,較佳係將矽或鋁之硫屬化合物(包括氧化物)層設置於電場發光介質層之陽極表面上,並將金屬鹵化物層或金屬氧化物層設置於電場發光介質層之陰極表面上。這種表面層可對有機電場發光裝置提供操作安定性。較佳地,該硫屬化合物包含SiOX(1X2)、AlOX(1X1.5)、SiON、SiAlON等;該金屬鹵化物包含LiF、MgF2、CaF2、稀土金屬氟化物等;以及該金屬氧化物包含CS2O、Li2O、MgO、SrO、BaO、CaO等。
較佳地,根據本發明之有機電場發光裝置,可將電子
傳輸化合物與還原性摻雜劑之混合區域或電洞傳輸化合物與氧化性摻雜劑之混合區域,設置電極對的至少一個表面上。於該情況中,電子傳輸化合物被還原成陰離子,因而自混合區域注入與傳輸電子至電場發光介質變得更容易。再者,電洞傳輸化合物被氧化成陽離子,因而自混合區域注入與傳輸電洞至電場發光介質變得更容易。較佳之氧化性摻雜劑係包括各種路易士酸及接受者化合物;較佳之還原性摻雜劑係包括鹼金屬、鹼金屬化合物、鹼土金屬、稀土金屬及其混合金屬。還原性摻雜劑層可使用作為電荷產生層來製備具有兩層或多層電場發光層和發射白光之電場發光裝置。
後文,將參照下述實例詳細說明本發明之有機電子材料化合物、該化合物之製備方法以及包含該化合物之裝置的發光性質:
化合物1-1之製備
將2-碘基苯(30 g,120.4 mmol)、4-溴基苯基硼酸(26
g,132.5 mmol)和Pd(PPh3)4(6.9 g,6.02 mmol)置於2M Na2CO3(150 mL)和甲苯(500 mL)之混合物中後,於100℃將該反應混合物加熱。4小時後,將該反應混合物冷卻至室溫,以乙酸乙酯(EA)萃取,以蒸餾水清洗,以MgSP4乾燥,經過減壓蒸餾並通過管柱過濾獲得化合物1-1(28 g,100.68 mmol,83.33%)。
化合物1-2之製備
將化合物1-1(28 g,100.68 mmol)與亞磷酸三乙基酯(300 mL)混合,將該反應混合物於150℃攪拌6小時。將該反應混合物冷卻至室溫,經過減壓蒸餾,以乙酸乙酯萃取,以蒸餾水清洗。將該反應混合物以MgSO4乾燥,經過減壓蒸餾並通過管柱過濾獲得化合物1-2(11 g,44.69 mmol,44.38%)。
化合物1-3之製備
將化合物1-2(30 g,101.29 mmol)、碘基苯(41.3 g,202.59 mmol)、CuI(9.6 g,50.64 mmol)和Cs2CO3(82.5 g,253.2 mmol)與甲苯(600 mL)混合,於50℃加熱該反應混合物。將乙二胺(EDA)(6.8 mL,101.29 mmol)加入至該反應混合物並迴流攪拌。14小時後,將該反應混合物冷卻至室溫,並加入蒸餾水。將該反應混合物以乙酸乙酯萃取,以MgSO4乾燥,經過減壓蒸餾並通過管柱過濾獲得化合物1-3(32 g,85.96 mmol,84.86%)。
化合物1-4之製備
將化合物1-3(32 g,85.96 mmol)溶解於四氫呋喃(THF)
(300 mL),於-78℃緩慢加入2.5 M之n-BuLi於丁烷之溶液(37.8 mL,94.55 mmol)於該反應混合物。1小時後,加入硼酸三甲酯(12.4 mL,111.7 mmol)。該反應混合物攪拌12小時,並加入蒸餾水至該反應混合物。將該反應混合物以乙酸乙酯萃取,以MgSO4乾燥,經過減壓蒸餾並通過管柱過濾獲得化合物1-4(20 g,59.31 mmol,69.00%)。
化合物1-5之製備
將化合物1-4(20 g,59.31 mmol)、1-溴基-2-硝基苯(14.3 g,71.17 mmol)、Pd(PPh3)4(2.7 g,2.37 mmol)、2M Na2CO3(75 mL)、甲苯(300 mL)和乙醇(70mL)混合後,該反應混合物經過迴流攪拌。5小時後,將該反應混合物冷卻至室溫,並加入蒸餾水。將該反應混合物以乙酸乙酯萃取,以MgSO4乾燥,經過減壓蒸餾並通過管柱過濾獲得化合物1-5(20 g,48.25 mmol,81.36%)。
化合物1-6之製備
將化合物1-5(20 g,48.25 mmol)和亞磷酸三乙基酯(200 mL)混合,將該反應混合物於150℃攪拌6小時。將該反應混合物冷卻至室溫,經過減壓蒸餾,以乙酸乙酯萃取並加入蒸餾水。將該反應混合物以MgSO4乾燥,經過減壓蒸餾並通過管柱過濾獲得化合物1-6(7 g,18.30 mmol,37.93%)。
化合物1-7之製備
將2,4-二氯基喹唑啉(30 g,151 mmol)、9-苯基-9H-咔唑-3-基硼酸(15.6 g,75.3 mmol)、Pd(PPh3)4(2.6 g,2.3
mmol)和Na2CO3(16 g,150 mmol)溶解於甲苯(300 mL)和蒸餾水(75 mL)之混合物,將該反應混合物於90℃攪拌2小時。所得有機層經過減壓蒸餾,並以MeOH研製。所得固體以二氯甲烷(MC)溶解,再經氧化矽過濾,並以MC和己烷研製獲得化合物1-7(9.3 g,51.4%)。
化合物C-2之製備
將化合物1-6(4.9 g,14.7 mmol)與化合物1-7(5 g,15.8 mmol)懸浮至二甲基甲醯胺(DMF)(80 mL)後,於室溫將60% NaH(948 mg,22 mmol)加入至該反應混合物。所得反應混合物攪拌12小時。加入純化水(1 L)後,減壓過濾混合物。所得固體以MeOH/EA研製、以MC溶解,經氧化矽過濾,再以二氯甲烷(MC)/正己烷研製獲得化合物C-2(5.3 g,51.5%)。
MS/FAB實測值702;計算值701.81
化合物2-1之製備
將1-溴基-2-硝基苯(15 g,0.074 mol)置於1 L雙頸圓底瓶中,加入9,9-二甲基-9H-茀-2-基硼酸(23 g,0.096 mol)、Pd(PPh3)4(4.2 g,0.003 mol)、2 M Na2CO3(111 mL)
和乙醇(111 mL),並加入甲苯(200 mL),將該反應混合物於120℃攪拌3小時。終止反應後,以蒸餾水清洗該反應混合物,並以乙酸乙酯萃取。所得有機層以MgSO4乾燥,並以旋轉蒸發器去除有機溶劑。所得物質經由管柱色層分析純化獲得化合物2-1(22 g,95%)。
化合物2-2之製備
將化合物2-1(24 g,0.076 mol)置於1 L雙頸圓底瓶中後,將亞磷酸三乙基酯(200 mL)和1,2-二氯基苯(200 mL)加入該反應混合物中。將該反應混合物於140℃攪拌12小時。終止反應後,蒸餾去除溶劑,以蒸餾水清洗該混合物,並以乙酸乙酯萃取。所得有機層以MgSO4乾燥,並以旋轉蒸發器去除有機溶劑。所得物質經由管柱色層分析純化獲得化合物2-2(7g,33%)。
化合物2-3之製備
將2,4-二氯基喹唑啉(50 g,251 mmol)和二苯并[b,d]呋喃-4-基硼酸(53.2 g,251 mmol)溶解於甲苯(1 L)和水(200 mL)之混合物後,將Pd(PPh3)4(14.5 g,12.5 mmol)和碳酸鈉(80 g,755 mmol)加入該反應混合物。將該反應混合物於80℃攪拌20小時,並冷卻至室溫。以氯化銨水溶液(200 mL)中止該反應後,將該反應混合物以乙酸乙酯(1 L)萃取,並以二氯甲烷(1 L)萃取該水層。所得有機層以無水硫酸鎂乾燥,並減壓去除有機溶劑。所得固體經氧化矽過濾,並減壓去除有機溶劑。所得固體以乙酸乙酯(100 mL)清洗獲得化合物2-3(50 g,74%)。
化合物C-34之製備
化合物2-2(34.6 g,122 mmol)溶解於DMF後,緩慢加入60% NaH(5.9 g,148 mmol)至該反應混合物,並於室溫攪拌1小時。將化合物2-3(51 g,147 mmol)加入該反應混合物,並於室溫攪拌20小時。將冰水緩慢滴入該反應混合物以中止反應,並過濾獲得該產生的固體。所得固體以水(1 L)、接著以MeOH(1 L)清洗。將所得固體乾燥並溶於CHCl3(4 L),以矽膠過濾去除無機物。將所得溶液去除溶劑以得固體。將所得固體以DMF再結晶可獲得化合物C-34(41 g,58%)。
MS/FAB實測值578;計算值577.67
化合物3-1之製備
化合物2-2(9.7 g,34.3 mol)、1-溴基-4-碘基苯(48.5 g,171.4 mmol)、CuI(3.3 g,17.1 mmol)、K3PO4(21.8 g,102.9 mmol)和乙二胺(2.3 mL,34.3 mmol)置於甲苯(500 mL)後,將該反應混合物迴流攪拌24小時。將該反應混合物以乙酸乙酯萃取,經減壓蒸餾,再經管柱以MC和己烷過濾可獲得化合物3-1(12.0 g,80.1%)。
化合物3-2之製備
化合物3-1(12.1 g,27.5 mmol)溶解於四氫呋喃(THF)(250 mL)後,於-78℃緩慢加入2.5 M之n-BuLi於丁烷之溶液(17.6 mL,44 mmol)至該反應混合物,將該反應混合物攪拌1小時。攪拌該反應混合物2小時同時緩慢加入B(Oi-Pr)3(12.6 mL,55 mmol)至該反應混合物。加入2 M HCl猝息反應混合物後,該反應混合物以蒸餾水和乙酸乙酯萃取。將所得物質以MC和己烷再結晶獲得化合物3-2(6.7 g,60%)。
化合物C-80之製備
將化合物2-3(3.2 g,9.2 mmol)、化合物3-2(3.7 g,9.2 mmol)、Pd(PPh3)4(532 mg,0.46 mmol)和Na2CO3(2.9 g,27.6 mmol)溶解於甲苯(55 mL)、EtOH(14 mL)和蒸餾水(14 mL)之混合物後,將反應混合物置於90℃攪拌2小時。該反應混合物以EA和水萃取,並經管柱以MC和己烷過濾獲得化合物C-80(4.5 g,75%)。
MS/FAB實測值654;計算值653.77
使用根據本發明之化合物製造OLED裝置。使用超音波依序以三氯乙烯、丙酮、乙醇及蒸餾水清洗有機發光二極體(OLED)裝置(Samsung Corning,Republic of Korea)之玻璃板上之透明電極ITO薄膜(15 Ω/sq),並儲存於異丙醇中。然後,將ITO基板裝配於真空氣相沉積裝置之基板夾持器中。將N1,N1'-([1,1’-聯苯]-4,4’-二基)雙(N1-(萘
-1-基)-N4,N4-二苯基苯-1,4,-二胺)置於該真空氣相沉積裝置之小室中,隨後對該裝置之腔室調控壓力至10-6托(torr)。隨後對該小室施加電流來蒸發上述物質,從而於ITO基板上形成厚度為60nm之電洞注入層。然後,將N,N’-二(4-聯苯基)-N,N’-二(4-聯苯基)-4,4’-二胺基聯苯導入該真空氣相沉積裝置之另一小室中,隨後對該小室施加電流來蒸發上述物質,從而於電洞注入層上形成厚度為20nm之電洞傳輸層。接著,將化合物C-5導入該真空氣相沉積裝置之小室中作為主體材料,並將化合物D-11導入另一小室中作為摻雜劑。以不同速率蒸發該兩種材料,從而以摻雜量4wt%沉積於該電洞傳輸層上而形成厚度為30 nm之發光層。然後,將2-(4-(9,10-二(萘-2-基)蒽-2-基)苯基)-1-苯基-1H-苯并[d]咪唑導入一小室中,並將8-羥基喹啉鋰(Lithium quinolate)導入另一小室中。以相同速率蒸發該兩種材料,從而以摻雜量50wt%沉積於該發光層上形成厚度為30 nm之電子傳輸層。然後,將喹啉鋰沉積於電子傳輸層上做為2nm之電子注入層,用另一真空氣相沉積裝置在電子注入層上形成厚度為150nm之鋁(Al)陰極而製造出OLED。用於該OLED裝置之化合物已各別於10-6托真空昇華予以純化。
所產生的OLED裝置發射亮度1,135cd/cm2之紅光,以及於5.1V之驅動電壓有15.2mA/cm2之電流密度。更進一步地,在亮度為5,000尼特減少至90%之亮度最小時間為70小時。
除了將化合物C-11作為主體材料並使用化合物D-11作為摻雜劑之外,如實施例1般製造OLED。
所產生的OLED裝置發射亮度1,010cd/cm2之紅光,以及於4.9V之驅動電壓有12.2mA/cm2之電流密度。更進一步地,在亮度為5,000尼特減少至90%之亮度最小時間為80小時。
除了將化合物C-34作為主體材料並使用化合物D-7作為摻雜劑之外,如實施例1般製造OLED。
所產生的OLED裝置發射亮度1,090cd/cm2之紅光,以及於6.0V之驅動電壓有7.3mA/cm2之電流密度。更進一步地,在亮度為5,000尼特減少至90%之亮度最小時間為140小時。
除了將化合物C-80作為主體材料並使用化合物D-7作為摻雜劑之外,如實施例1般製造OLED。
所產生的OLED裝置發射亮度1,180cd/cm2之紅光,以及於5.8V之驅動電壓有7.9mA/cm2之電流密度。更進一步地,在亮度為5,000尼特減少至90%之亮度最小時間為100小時。
除了將化合物C-103作為主體材料並使用化合物D-6作為摻雜劑之外,如實施例1般製造OLED。
所產生的OLED裝置發射亮度1,100cd/cm2之紅光,以及於5.1V之驅動電壓有16.4mA/cm2之電流密度。更進一步地,在亮度為5,000尼特減少至90%之亮度最小時間為90小時。
除了將厚度30nm之發光層沉積於以4,4’-N,N’-二咔唑基-聯苯(CBP)作為主體材料並以化合物D-11作為摻雜劑之電洞傳輸層,再以鋁(III)雙(2-甲基-8-喹啉)-4-苯基酚沉積為厚度10nm之電洞阻擋層之外,如實施例1般製造OLED。
所產生的OLED裝置發射亮度1,000cd/cm2之紅光,以及於8.2V之驅動電壓有20.0mA/cm2之電流密度。更進一步地,在亮度為5,000尼特減少至90%之亮度最小時間為10小時。
與傳統材料相比,根據本發明之有機電場發光化合物具有較優的發光效率與較長壽命。此外,使用根據本發明之有機電場發光化合物作為主體材料之裝置,不僅有卓越的發光特性,亦可藉由減少驅動電壓以增加電能效率,因此可改良耗電量。
Claims (6)
- 一種下列式1表示之化合物,
- 如申請專利範圍第1項所述之化合物,其中在L1與L2、R1至R5、R6至R8和R11至R17基中之該經取代之(伸)烷基、經取代之烯基、經取代之炔基、經取代之伸環烷基、經取代之環烷基、經取代之雜環烷基、經取代之(伸)芳基、經取代之(伸)雜芳基和經取代之芳環的取代 基,各獨立為至少一個選自下列所組成群組者:氘、鹵素、經鹵素取代或未經取代之(C1-C30)烷基、(C6-C30)芳基、經(C1-C30)烷基或(C6-C30)芳基取代或未經取代之3員至30員雜芳基、(C3-C30)環烷基、3員至7員雜環烷基、三(C1-C30)烷基矽基、三(C6-C30)芳基矽基、二(C1-C30)烷基(C6-C30)芳基矽基、(C1-C30)烷基二(C6-C30)芳基矽基、(C2-C30)烯基、(C2-C30)炔基、氰基、咔唑基、二(C1-C30)烷基胺基、經(C1-C30)烷基取代或未經取代之二(C6-C30)芳基胺基、(C1-C30)烷基(C6-C30)芳基胺基、二(C6-C30)芳基硼羰基、二(C1-C30)烷基硼羰基、(C1-C30)烷基(C6-C30)芳基硼羰基、(C6-C30)芳基(C1-C30)烷基、(C1-C30)烷基(C6-C30)芳基、羧基、硝基和羥基。
- 如申請專利範圍第1項所述之化合物,其中L1和L2各獨立表示單鍵、3員至30員伸雜芳基、(C6-C30)伸芳基、或(C6-C30)伸環烷基;X1係表示CH或N;Y1至Y3各獨立表示-O-、-S-、-CR6R7-或-NR8-,限制條件為Y2和Y3不會同時存在;R1至R5各獨立表示氫、氘、鹵素、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之3員至30員雜芳基、N-咔唑基、-NR11R12、或-SiR13R14R15;或R1至R5各獨立連結至一個或多個相鄰取代基而形成其中一個或多個碳原 子可被至少一個選自氮、氧和硫之雜原子置換之單環或多環之(C5-C30)脂族環或芳環;R6至R8各獨立代表氫、氘、鹵素、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之3員至30員雜芳基;或R6至R8各獨立連結至一個或多個相鄰取代基而形成其中一個或多個碳原子可被至少一個選自氮、氧和硫之雜原子置換之單環或多環之(C5-C30)脂族環或芳環;R11至R15各獨立代表經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之3員至30員雜芳基;以及L1和L2之該伸芳基、伸雜芳基和伸環烷基,和R1至R5和R11至R15之該烷基、芳基和雜芳基,可經至少一個選自下列所組成群組之取代基取代:氘、鹵素、經鹵素取代或未經取代之(C1-C30)烷基、(C6-C30)芳基、(C1-C30)烷基(C6-C30)芳基、經(C1-C30)烷基或(C6-C30)芳基取代或未經取代之3員至30員雜芳基、(C3-C30)環烷基、三(C6-C30)芳基矽基、經(C1-C30)烷基取代或未經取代之二(C6-C30)芳基胺基、和(C6-C30)芳基(C1-C30)烷基。
- 如申請專利範圍第1項所述之化合物,其中式1中之部分係選自以下結構:
- 如申請專利範圍第1項所述之化合物,其中式1所表示之該化合物係選自下列所組成群組:
- 一種有機電場發光裝置,包括申請專利範圍第1項所述之化合物。
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