CN103827119A - 新颖的有机电致发光化合物和使用该化合物的有机电致发光器件 - Google Patents
新颖的有机电致发光化合物和使用该化合物的有机电致发光器件 Download PDFInfo
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- CN103827119A CN103827119A CN201280045820.1A CN201280045820A CN103827119A CN 103827119 A CN103827119 A CN 103827119A CN 201280045820 A CN201280045820 A CN 201280045820A CN 103827119 A CN103827119 A CN 103827119A
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- yuan
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 144
- 238000005401 electroluminescence Methods 0.000 title claims abstract description 20
- 125000003118 aryl group Chemical group 0.000 claims description 61
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 47
- 125000001072 heteroaryl group Chemical group 0.000 claims description 40
- 229910052736 halogen Inorganic materials 0.000 claims description 31
- 150000002367 halogens Chemical class 0.000 claims description 29
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 24
- 229910052805 deuterium Inorganic materials 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 150000002431 hydrogen Chemical group 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 125000001769 aryl amino group Chemical group 0.000 claims description 10
- 229910052796 boron Inorganic materials 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- 125000002723 alicyclic group Chemical group 0.000 claims description 9
- 125000005104 aryl silyl group Chemical group 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 239000005864 Sulphur Substances 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 5
- 125000001118 alkylidene group Chemical group 0.000 claims description 4
- 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 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000003968 arylidene group Chemical group [H]C(c)=* 0.000 claims 3
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- 239000002585 base Substances 0.000 description 46
- -1 aryl carbazole compound Chemical class 0.000 description 39
- 239000011541 reaction mixture Substances 0.000 description 38
- 238000002360 preparation method Methods 0.000 description 36
- 239000010410 layer Substances 0.000 description 33
- 239000000463 material Substances 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 30
- 238000003756 stirring Methods 0.000 description 24
- 238000002156 mixing Methods 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000012044 organic layer Substances 0.000 description 14
- 239000002019 doping agent Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000758 substrate Substances 0.000 description 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 10
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 8
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000004646 arylidenes Chemical group 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 6
- 125000005561 phenanthryl group Chemical group 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 6
- 230000008021 deposition Effects 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 125000005605 benzo group Chemical group 0.000 description 4
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 4
- 229910052741 iridium Inorganic materials 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001725 pyrenyl group Chemical group 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-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
- 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
- 239000002253 acid Substances 0.000 description 3
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 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 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 3
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- 238000004020 luminiscence type Methods 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
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000002971 oxazolyl group Chemical group 0.000 description 3
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 3
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- 125000003226 pyrazolyl group Chemical group 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000005493 quinolyl group Chemical group 0.000 description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 125000000335 thiazolyl group Chemical group 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 125000004306 triazinyl group Chemical group 0.000 description 3
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- BTTNYQZNBZNDOR-UHFFFAOYSA-N 2,4-dichloropyrimidine Chemical compound ClC1=CC=NC(Cl)=N1 BTTNYQZNBZNDOR-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
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 2
- XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical compound CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 150000003851 azoles Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical group CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 2
- 125000000259 cinnolinyl group Chemical class N1=NC(=CC2=CC=CC=C12)* 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 2
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 2
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 2
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- IDQUIFLAFFZYEX-UHFFFAOYSA-N (3-carbazol-9-ylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=C1 IDQUIFLAFFZYEX-UHFFFAOYSA-N 0.000 description 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- LPOQWSWPRAGSBK-UHFFFAOYSA-N 1,2-dibromo-3-nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC(Br)=C1Br LPOQWSWPRAGSBK-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
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- HBWATGYSAHIWIX-UHFFFAOYSA-N 2,3-dihydrothiophen-5-ylboronic acid Chemical compound OB(O)C1=CCCS1 HBWATGYSAHIWIX-UHFFFAOYSA-N 0.000 description 1
- SSABEFIRGJISFH-UHFFFAOYSA-N 2-(2,4-difluorophenyl)pyridine Chemical compound FC1=CC(F)=CC=C1C1=CC=CC=N1 SSABEFIRGJISFH-UHFFFAOYSA-N 0.000 description 1
- VOZBMWWMIQGZGM-UHFFFAOYSA-N 2-[4-(9,10-dinaphthalen-2-ylanthracen-2-yl)phenyl]-1-phenylbenzimidazole Chemical class C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC=C(C=2C=C3C(C=4C=C5C=CC=CC5=CC=4)=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C3=CC=2)C=C1 VOZBMWWMIQGZGM-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
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- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
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- 150000003384 small molecules Chemical class 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003527 tetrahydropyrans Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 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
Classifications
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- C07D491/04—Ortho-condensed systems
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Abstract
本发明涉及新颖的有机发光化合物以及包含该化合物的有机电致发光器件。本发明的化合物具有高的发光效率和长的工作寿命。因此,该化合物可生产改善功率消耗的有机电致发光器件。
Description
技术领域
本发明涉及新颖的有机电致发光化合物以及使用该化合物的有机电致发光器件。
背景技术
电致发光(EL)器件是一种自发光器件,其相对于其他类型的显示器件的优势在于提供了更宽的可视角、更高的对比度并具有更快速的响应时间。伊斯曼柯达公司(Eastman Kodak)通过使用小分子(芳族二胺)和铝配合物作为形成发光层的材料,首先开发了一种有机EL器件[Appl.Phys.Lett.(应用物理学报)51,913,1987]。
有机EL器件中决定发光效率的最重要的因素是发光材料。迄今为止,荧光材料被广泛地用作发光材料。但是,基于电致发光机理,开发磷光材料是理论上将发光效率增加4倍的最佳方法之一。铱(III)络合物是众所周知的磷光材料,包括二(2-(2'-苯并噻吩基)-吡啶根合-N,C3')(乙酰丙酮酸根合)铱((acac)Ir(btp)2)、三(2-苯基吡啶)铱(Ir(ppy)3)和二(4,6-二氟苯基吡啶合-N,C2)吡啶甲酸根合(picolinato)铱(Firpic),分别作为红色、绿色和蓝色材料。特别是近来在日本、欧洲和美国,人们正在对大量磷光材料进行研究。
目前,已知4,4'-N,N'-二咔唑-联苯(CBP)是最广泛用作磷光物质的基质材料。此外,已知有机EL器件使用浴铜灵(bathocuproine)(BCP)或二(2-甲基-8-羟基喹啉合(quinolinate))(4-苯基苯酚)铝(III)(BAlq)作为空穴阻挡层;日本先锋公司(Pioneer)等开发了一种高性能有机EL器件,其采用了BAlq的衍生物作为基质材料。
虽然这些材料提供良好的发光特征,它们具有下述不足:因为它们的玻璃化转变温度低和热稳定性差,在真空中的高温沉积过程中,它们可能发生降解。因为有机EL器件的功率效率是由[(π/电压)×电流效率]确定的,功率效率与电压成反比,因此应升高功率效率以降低功耗。尽管包括磷光材料的有机EL器件提供比含有荧光材料的器件更高的电流效率(cd/A),使用常规磷光材料如BAlq或CBP的有机EL器件的驱动电压比使用荧光材料的器件的更高。因此,对于功率效率(lm/W)而言,使用常规磷光材料的EL器件没有优势。此外,有机EL器件的工作寿命较短。
韩国专利No.KR0948700公开了用于有机EL器件的化合物为用包括氮原子的杂芳基取代的芳基咔唑化合物。但是,它没有公开在氮位置稠合的咔唑化合物,该化合物直接或间接地连接到用咔唑基取代的杂芳基。
发明内容
技术问题
本发明的目的是提供一种有机电致发光化合物,该化合物使器件具有高的发光效率和长的工作寿命并具有合适的色彩协调;本发明还提供了一种采用所述化合物作为发光材料的有机电致发光器件,其具有高的效率和长的寿命。
解决问题的方法
本发明的发明人发现可以通过如下通式1表示的化合物来实现上述目的:
其中
L1和L2各自独立地表示单键、取代或未取代的3元至30元杂亚芳基、取代或未取代的(C6-C30)亚芳基或者取代或未取代的(C3-C30)环亚烷基;
X1和X2表示CH或N;
Y1和Y2各自独立地表示-O-、-S-、-CR5R6-或–NR7-,前提是Y1和Y2不同时存在;
Ar表示氢、氘、卤素、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、或取代或未取代的3元-30元杂芳基,或N-咔唑基;
R1至R4各自独立地表示氢、氘、卤素、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、取代或未取代的3元至30元杂芳基、取代或未取代的(C3-C30)环烷基、取代或未取代的5元至7元杂环烷基、取代或未取代的(C6-C30)芳基(C1-C30)烷基、-NR11R12、-SiR13R14R15、-SR16、-OR17、氰基、硝基或羟基;或者它们与相邻取代基相连以形成单环或多环,(C5-C30)脂环或芳环,其碳原子可以被至少一个选自氮、氧和硫的杂原子替代;
R5至R7和R11至R17各自独立地表示氢、氘、卤素、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、取代或未取代的3元至30元杂芳基;取代或未取代的5元至7元杂环烷基、或取代或未取代的(C3-C30)环烷基;或者它们与相邻取代基相连以形成单环或多环,(C5-C30)脂环或芳环,其碳原子可以被至少一个选自氮、氧和硫的杂原子代替;
a、b、c和d各自独立地表示1-4的整数;当a、b、c或d是大于或等于2的整数时,每一个R1、每一个R2、每一个R3或每一个R4是相同或不同的;以及
所述杂环烷基、杂亚芳基、和杂芳基含有至少一个选自B、N、O、S、P(=O)、Si和P的杂原子。
发明的有益效果
本发明的有机电致发光化合物可制造具有高发光效率和长工作寿命的有机电致发光器件。
此外,由于本发明的化合物具有较高的传输电子效率,因而在制备器件时可以防止结晶。此外,所述化合物具有良好的成层性,可改善器件的电流特性。因此,它们可制备出具有较低的驱动电压和增强的功率效率的有机电致发光器件。
本发明的实施方式
下面将详细描述本发明。但是,以下描述是用于解释本发明,而不是为了以任意方式限制本发明的范围。
本发明涉及用上式1表示的有机电致发光化合物以及包含该化合物的有机电致发光器件。
本文中,“(C1-C30)(亚)烷基”意指直链或支链的、具有1-30个碳原子的(亚)烷基,其中碳原子的数目优选是1-20,更优选是1-10,且包括甲基、乙基、正丙基、正丁基、异丁基、叔丁基等;“(C2-C30)烯基”意指直链或支链的、具有2-30个碳原子的烯基,其中碳原子的数目优选是2-20,更优选是2-10,且包括乙烯基、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;“(C2-C30)炔基”是直链或支链的、具有2-30个碳原子的炔基,其中碳原子的数目优选是2-20,更优选是2-10,且包括乙炔基、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;“(C3-C30)环烷基”是具有3-30个碳原子的单环或多环烃,其中碳原子的数目优选是3-20,更优选是3-7,且包括环丙基、环丁基、环戊基、环己基等;“3元-7元杂环烷基”是包括至少一个选自B、N、O、S、P(=O)、Si和P的杂原子(优选的O、S和N)和3-7个环骨架原子的环烷基,且包括四氢呋喃、吡咯烷、四氢噻吩(thiolan)、四氢吡喃等;“(C6-C30)(亚)芳基”是衍生自具有6-30个碳原子的芳烃的单环或稠环,其中碳原子的数量优选为6-20,更优选为6-15,并且包括苯基、联苯基、三联苯基、萘基、芴基、菲基、蒽基、茚基、苯并[9,10]菲基(triphenylenyl)、芘基、并四苯基(tetracenyl)、苝基(perylenyl)、基(chrysenyl)、并四苯基(naphthacenyl)、荧蒽基(fluoranthenyl)等;“3元-30元杂(亚)芳基”是包括至少一个(优选的1-4个)选自B、N、O、S、P(=O)、Si和P的杂原子和3-30个环骨架原子的芳基;是单环或与至少一个苯环缩合的稠环;优选的包括5–20个、更优选的包括5-15个环骨架原子;可以是部分饱和的;可以是将至少一个杂芳基或芳基通过单键与杂芳基连接而形成的基团;且包括单环类的杂芳基,包括呋喃基、噻吩基、吡咯基、咪唑基、吡唑基、噻唑基、噻二唑基、异噻唑基、异唑基、唑基、二唑基、三嗪基、四嗪基、三唑基、四唑基、呋咱基(furazanyl)、吡啶基、吡嗪基、嘧啶基、哒嗪基等;包括稠环类的杂芳基,包括苯并呋喃基(benzofuranyl)、苯并噻吩基、异苯并呋喃基、二苯并呋喃基、二苯并噻吩基、苯并咪唑基、苯并噻唑基、苯并异噻唑基、苯并异噁唑基、苯并噁唑基、异吲哚基、吲哚基、吲唑基、苯并噻二唑基、喹啉基、异喹啉基、噌啉基(cinnolinyl)、喹唑啉基、喹喔啉基(quinoxalinyl)、咔唑基、吩噁嗪基(phenoxazinyl)、菲啶基(phenanthridinyl)、苯并间二氧杂环戊烯基(benzodioxolyl)等。此外,“卤素”包括F、Cl、Br和I。
本文所用术语“取代或未取代的”中的“取代”指的是某个官能团中的氢原子被另一个原子或基团(即取代基)取代。所述L1、L2、Ar、R1至R7以及R11至R17基团中所述取代的烷基、取代的(亚)芳基、取代的杂(亚)芳基、取代的环(亚)烷基、取代的杂环烷基和取代的芳烷基的取代基各自独立地是至少一种选自下组的基团:氘;卤素;未取代的或被卤素取代的(C1-C30)烷基;(C6-C30)芳基;未取代的或用(C1-C30)烷基或(C6-C30)芳基取代的3元至30元杂芳基;(C3-C30)环烷基;5元至7元杂环烷基;三(C1-C30)烷基甲硅烷基;三(C6-C30)芳基甲硅烷基;二(C1-C30)烷基(C6-C30)芳基甲硅烷基;(C1-C30)烷基二(C6-C30)芳基甲硅烷基;(C2-C30)烯基;(C2-C30)炔基;氰基;N-咔唑基;二(C1-C30)烷基氨基;二(C6-C30)芳基氨基;(C1-C30)烷基(C6-C30)芳基氨基;二(C6-C30)芳基硼羰基(boronyl);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;硝基和羟基。
在上述通式1中,L1和L2各自独立地代表单键、3元至30元杂亚芳基、或(C6-C30)亚芳基;X1和X2各自独立地表示CH或N;Y1和Y2各自独立地表示-O-、-S-、-CR5R6-或–NR7-,前提是Y1和Y2不同时存在;Ar表示氢、氘、卤素、(C1-C30)烷基、(C6-C30)芳基、3元至30元杂芳基、或N-咔唑基;R1至R4各自独立地表示氢、氘、卤素、(C1-C30)烷基、(C6-C30)芳基、3元至30元杂芳基、N-咔唑基、或-SiR13R14R15;R5至R7各自独立地表示(C1-C30)烷基、(C6-C30)芳基、或3元至30元杂芳基;或者R5和R6相互结合以形成单环或多环,(C5-C30)脂环或芳环,其碳原子可以被至少一个选自氮、氧和硫的杂原子代替;R13至R15各自独立地表示(C1-C30)烷基、(C6-C30)芳基、或3元至30元杂芳基;以及L1和L2中的亚芳基和杂亚芳基,Ar中的烷基、芳基、杂芳基和N-咔唑基,R1至R4中的烷基、芳基、杂芳基和N-咔唑基,R5至R7和R13至R15中的烷基、芳基和杂芳基可被至少一个选自下组的基团取代:氘;卤素;未取代或被卤素取代的(C1-C30)烷基;(C6-C30)芳基;未取代或者被(C1-C30)烷基或(C6-C30)芳基取代的3元至30元杂芳基;(C3-C30)环烷基;N-咔唑基;二(C1-C30)烷基氨基;二(C6-C30)芳基氨基;(C1-C30)烷基(C6-C30)芳基氨基;(C6-C30)芳基(C1-C30)烷基;和(C1-C30)烷基(C6-C30)芳基。
在上述通式1中,L1和L2各自独立地优选是单键或者取代的或未取代的(C6-C20)亚芳基,其中可用(C1-C6)烷基或(C6-C20)芳基取代所述取代的亚芳基。
Y1和Y2各自独立地表示-O-、-S-、-CR5R6-或–NR7-,其中R5和R6各自独立地优选为(C1-C6)烷基或(C6-C20)芳基,或者相互结合以形成单环或多环,(C5-C30)脂环或芳环,且R7优选为取代的或未取代的(C6-C20)芳基,其中可用氘、卤素、(C1-C6)烷基或(C6-C12)芳基氨基取代所述取代的芳基。
Ar优选为氢、取代的或未取代的(C6-C20)芳基、或取代的或未取代的5-至15-元杂芳基,其中可用氘、卤素、(C1-C6)烷基、(C6-C20)芳基或5-至15-元杂芳基取代所述取代的芳基和取代的杂芳基。
R1至R4各自独立地优选为氢、取代的或未取代的(C1-C6)烷基、取代的或未取代的(C6-C20)芳基、取代的或未取代的5-至15-元杂芳基或者-SiR13R14R15,其中可用(C1-C6)烷基取代所述取代的烷基、取代的芳基和取代的杂芳基,且R13至R15各自独立地优选为(C1-C6)烷基或(C6-C20)芳基。
在上述通式1中,L1和L2各自独立地优选是单键或者取代的或未取代的(C6-C20)亚芳基;Y1和Y2各自独立地表示-O-、-S-、-CR5R6-或–NR7-,其中R5和R6各自独立地优选为(C1-C6)烷基或C6-C20)芳基,或者相互结合以形成单环或多环,(C5-C30)脂环或芳环,且R7优选为取代的或未取代的(C6-C20)芳基;Ar优选为氢、取代的或未取代的(C6-C20)芳基、取代的或未取代的5-至15-元杂芳基;R1至R4各自独立地优选为氢、取代的或未取代的(C1-C6)烷基、取代的或未取代的(C6-C20)芳基、取代的或未取代的5-至15-元杂芳基或者-SiR13R14R15,且R13至R15各自独立地优选为(C1-C6)烷基或(C6-C20)芳基。
具体来说,L1和L2各自独立地代表单键、亚苯基、亚联苯基、亚三联苯基、亚茚基、亚芴基、亚苯并[9,10]菲基、亚芘基、亚苝基、亚基(crysenylene)、亚并四苯基、亚荧蒽基(fluoranthenylene)、亚噻吩基、亚吡咯基、亚吡唑基、亚噻唑基、亚噁唑基、亚噁二唑基、亚三嗪基、亚四嗪基、亚三唑基、亚呋咱基、亚吡啶基、亚苯并呋喃基、亚苯并噻吩基、亚吲哚基、亚苯并咪唑基、亚苯并噻唑基、亚苯并异噻唑基、亚苯并异噁唑基、亚苯并噁唑基、亚苯并噻二唑基、亚二苯并呋喃基或亚二苯并噻吩基;Ar代表氢、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、正己基、正庚基、正辛基、2-乙基己基、正壬基、癸基、十二烷基、十六烷基、三氟甲基、全氟乙基、三氟乙基、全氟丙基、全氟丁基、苯基、联苯基、芴基、荧蒽基(fluoranthenyl)、苯并[9,10]菲基、芘基、基(crysenyl)、并四苯基、基、吡啶基、吡咯基、呋喃基、噻吩基、咪唑基、苯并咪唑基、喹啉基、三嗪基、苯并呋喃基、二苯并呋喃基、苯并噻吩基、二苯并噻吩基、吡唑基、吲哚基、咔唑基、噻唑基、噁唑基、苯并噻唑基、苯并噁唑基、菲咯啉基、喹喔啉基或N-咔唑基;R1至R4各自独立地代表氢、氘、氯、氟、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、正己基、正庚基、正辛基、2-乙基己基、正壬基、癸基、十二烷基、十六烷基、三氟甲基、全氟乙基、三氟乙基、全氟丙基、全氟丁基、苯基、萘基、蒽基、联苯基、芴基、荧蒽基(fluoranthenyl)、苯并[9,10]菲基、芘基、基、并四苯基、基、吡啶基、吡咯基、呋喃基、噻吩基、咪唑基、苯并咪唑基、吲哚基、吡嗪基、嘧啶基、哒嗪基、喹啉基、三嗪基、苯并呋喃基、二苯并呋喃基、苯并噻吩基、二苯并噻吩基、吡唑基、吲哚基、咔唑基、噻唑基、噁唑基、苯并噻唑基、苯并噁唑基、菲咯啉基、N-咔唑基、三甲基甲硅烷基、三乙基甲硅烷基、三丙基甲硅烷基、三(叔丁基)甲硅烷基、叔丁基二甲基甲硅烷基、二甲基苯基甲硅烷基、甲基二苯基甲硅烷基或三苯基甲硅烷基;在L1、L2、Ar和R1至R4中的取代基各自可用至少一种选自下组的基团来取代:氘、氯、氟、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、正己基、正庚基、正辛基、2-乙基己基、正壬基、癸基、十二烷基、十六烷基、三氟甲基、全氟乙基、三氟乙基、全氟丙基、全氟丁基、苯基、萘基、联苯基、9,9-二甲基芴基、9,9-二苯基芴基、荧蒽基、苯并[9,10]菲基、芘基、基、并四苯基、基、二甲基氨基、二乙基氨基、甲基苯基氨基、二苯基氨基、三甲基甲硅烷基、三乙基甲硅烷基、三丙基甲硅烷基、三(叔丁基)甲硅烷基、叔丁基二甲基甲硅烷基、二甲基苯基甲硅烷基、甲基二苯基甲硅烷基、三苯基甲硅烷基、N-咔唑基和N-苯基咔唑基。
其中R5、R6和R7如上文的通式1所定义。
本发明的代表性化合物包括以下化合物:
本发明的有机电致发光化合物可通过以下反应方案来制备。
[反应方案1]
[反应方案2]
其中L1、L2、Ar、X1、X2、Y1、Y2、R1至R4、a、b、c和d如上式1所定义,Hal表示卤素。
此外,本发明提供了一种包含通式1化合物的有机电致发光器件。所述有机电致发光器件包括第一电极、第二电极以及所述第一电极和第二电极之间的至少一层有机层。所述有机层包含至少一种本发明通式1的化合物。此外,所述有机层包括发光层,其中包含通式1的化合物作为基质材料。
此外,与本发明的基质材料一起使用用于有机电致发光器件的磷光掺杂剂可选自由以下通式2表示的化合物:
M1L101L102L103---------------------(2)
其中M1选自Ir、Pt、Pd和Os;L101、L102和L103各自独立地选自如下结构:
R201至R203各自独立地表示氢、氘、未取代的或被卤素取代的(C1-C30)烷基、未取代的或被(C1-C30)烷基取代的(C6-C30)芳基、或者卤素;
R204至R219各自独立地表示氢、氘、取代或未取代的(C1-C30)烷基、取代或未取代的(C1-C30)烷氧基、取代或未取代的(C3-C30)环烷基、取代或未取代的(C2-C30)烯基、取代或未取代的(C6-C30)芳基、取代或未取代的单-或二-(C1-C30)烷基氨基、取代或未取代的单-或二-(C6-C30)芳基氨基、SF5、取代或未取代的三(C1-C30)烷基甲硅烷基、取代或未取代的二(C1-C30)烷基(C6-C30)芳基甲硅烷基、取代或未取代的三(C6-C30)芳基甲硅烷基、氰基或者卤素;
R220至R223各自独立地表示氢、氘、未取代的或被卤素取代的(C1-C30)烷基、或者未取代的或被(C1-C30)烷基取代的(C6-C30)芳基;
R224和R225各自独立地表示氢、氘、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、或卤素,或者R224和R225可以与相邻取代基相连形成单环或多环,(C5-C30)脂环或芳环;
R226表示取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、取代或未取代的5元至30元杂芳基或者卤素;
R227至R229各自独立地表示氢、氘、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基或者卤素;
Q表示R231至R242各自独立地表示氢、氘、未取代的或被卤素取代的(C1-C30)烷基、(C1-C30)烷氧基、卤素、取代或未取代的(C6-C30)芳基、氰基或者取代或未取代的(C5-C30)环烷基,或者R231至R242中的每一个可通过亚烷基或亚烯基与相邻取代基相连以形成螺环或稠环,或者可通过亚烷基或亚烯基与R207或R208相连以形成饱和或不饱和的稠环。
通式2中的掺杂剂包括下述:
除了通式1表示的化合物之外,本发明的有机电致发光器件还可包括至少一种选自下组的化合物:基于芳胺的化合物和基于苯乙烯基芳胺的化合物。
在本发明的有机电致发光器件中,所述有机层还可包含至少一种选自元素周期表第I族金属、第II族金属、第四周期过渡金属、第五周期过渡金属、镧系金属和d-过渡元素的有机金属的金属,或者至少一种包含所述金属的络合物。所述有机层可包括发光层和电荷产生层。
此外,除了本发明的化合物之外,所述有机电致发光器件可通过进一步包含至少一层发光层来发射白光,所述发光层包含蓝光电致发光化合物、红光电致发光化合物或者绿光电致发光化合物。
优选地,在本发明的有机电致发光器件中,可以在一个或两个电极的内表面上放置至少一层选自硫属化物层、金属卤化物层和金属氧化物层的层(以下称为表面层摂)。具体地,优选将硅或铝的硫属化物(包括氧化物)层放置在电致发光介质层的阳极表面上,将金属卤化物层或金属氧化物层放置在电致发光介质层的阴极表面上。所述表面层为有机电致发光器件提供了工作稳定性。优选地,所述硫属化物包括SiOX(1≤X≤2)、AlOX(1≤X≤1.5)、SiON、SiAlON等;所述金属卤化物包括LiF、MgF2、CaF2、稀土金属氟化物等;所述金属氧化物包括Cs2O、Li2O、MgO、SrO、BaO、CaO等。
优选地,在本发明的有机电致发光器件中,电子传输化合物和还原性掺杂剂的混合区或者空穴传输化合物和氧化性掺杂剂的混合区可放置在电极对中的至少一个表面上。在这种情况下,电子传输化合物被还原成阴离子,这样电子从混合区注入并传输到电致发光介质中变得更加容易。此外,空穴传输化合物被氧化成阳离子,从而空穴从混合区注入并传输到电致发光介质中变得更加容易。优选地,所述氧化性掺杂剂包括各种路易斯酸和受体化合物,所述还原性掺杂剂包括碱金属、碱金属化合物、碱土金属、稀土金属及其混合物。可以采用还原性掺杂剂层作为电荷产生层来制备具有两层或更多层电致发光层并发射白光的电致发光器件。
下文参照以下实施例详细描述所述有机电致发光化合物、所述化合物的制备方法、以及包含本发明化合物的器件的发光性质:
实施例1:化合物C-40的制备
化合物1-1的制备
将2-溴-9,9-二甲基-9H-芴(50克,183.0毫摩尔)、2-氯苯胺(38毫升,366.1毫摩尔)、Pd(OAc)2(1.2克,5.5毫摩尔)、P(t-Bu)3(8.8毫升,18.3毫摩尔)、NaOt-Bu(35克,366.1毫摩尔)和甲苯(180毫升)混合后,将反应混合物回流搅拌2.5小时。终止反应后,过滤反应混合物,并用二氯甲烷洗涤滤饼。用纯净水洗涤所得有机层,用MgSO4干燥,并在减压下浓缩。然后,通过硅胶过滤原油,并在减压下浓缩剩余溶液,得到化合物1-1(47克,80%)。
化合物1-2的制备
将化合物1-1(46克,143.8毫摩尔)、Pd(OAc)2(968毫克,4.3毫摩尔)、二-叔丁基(甲基)四氟硼酸磷(2克,4.31毫摩尔)和DMAc(200毫升)混合之后,将该反应混合物回流搅拌21小时。终止反应后,过滤反应混合物,并用二氯甲烷洗涤滤饼。用纯净水洗涤所得有机层,用MgSO4干燥,并在减压下浓缩。然后,通过硅胶过滤原油,并在减压下浓缩剩余溶液,得到化合物1-2(17克,53%)。
化合物1-3的制备
将3-(9H-咔唑-9-基)苯基硼酸(7克,24.4毫摩尔)、2,4-二氯嘧啶(3.9克,26.9毫摩尔)、Pd(PPh3)4(845毫克,0.7毫摩尔)、K2CO3(6.7克,48.8毫摩尔)、甲苯(100毫升)、EtOH(25毫升)和纯净水(25毫升)混合后,将反应混合物在回流搅拌5小时。终止反应后,将该反应混合物冷却到室温,过滤,用MgSO4干燥,并在减压下浓缩,且通过硅胶过滤。在减压下浓缩剩余溶液,得到化合物1-3(6克,70%)。
化合物C-40的制备
将化合物1-2(6.6克,18.6毫摩尔)溶解在DMF(120毫升)中,在0℃时加入NaH(813毫克,20.3毫摩尔),并搅拌10分钟。向反应混合物中加入化合物1-3(4.8克,16.9毫摩尔),并搅拌19小时。反应终止之后,在该反应混合物中加入MeOH。将所得固体通过硅胶进行过滤,用DMF进行重结晶,得到化合物C-40(4克,36%)。
MS/FAB的实测值603;计算值602.73
实施例2:化合物C-94的制备
化合物2-1的制备
将1-溴-2-硝基苯(85克,0.42摩尔)、二苯并[b,d]噻吩-2-基硼酸(80克,0.35摩尔)、Pd(PPh3)4(20克,0.018摩尔)、K2CO3(116克,1.0摩尔)、甲苯(1700毫升)、EtOH(440毫升)、和蒸馏水(440毫升)混合后,在120℃下将反应混合物搅拌12小时。反应终止后,用EA提取反应混合物。用MgSO4干燥所得有机层,过滤、减压蒸馏以去除溶剂,并通过柱过滤后得到化合物2-1(93克,87%)。
化合物2-2的制备
将化合物2-1(88克,0.29摩尔)、P(OEt)3(960毫升,0.4M)和亚磷酸三乙酯(960毫升)混合之后,将该反应混合物在90℃下搅拌12小时。终止反应之后,蒸馏该反应混合物以除去亚磷酸三乙酯,并通过柱过滤得到化合物2-2(40克,70%)。
化合物C-94的制备
将NaH60%(0.9克,0.02摩尔)溶解在DMF(50毫升)中后,搅拌溶液。将化合物2-2(4.69克,0.017摩尔)溶解在DMF(20毫升)中后,将该溶液添加至NaH溶液中,并搅拌1小时。将化合物1-3(6.1克,0.017摩尔)溶解在DMF(100毫升)中后,搅拌该溶液。然后,将化合物2-2的混合溶液添加到化合物1-3的混合溶液,并搅拌12小时。终止反应后,过滤所得黄色固体,并重结晶得到化合物C-94(3克,30%)。
MS/FAB的实测值593;计算值592.71
实施例3:化合物C-105的制备
化合物3-1的制备
将咔唑(26克,155.49毫摩尔)、4-溴碘苯(87克,310.9毫摩尔)、CuI(14.8克,77.74毫摩尔)、乙二胺(9.3克,155.49毫摩尔)、K3PO4(99克,499.47毫摩尔)和甲苯(1000毫升)混合后,回流搅拌反应混合物。15小时后,将反应混合物冷却至室温,并减压过滤以去除CuI和K3PO4。用MC提取剩余溶液,用蒸馏水洗涤,并随后通过柱过滤,得到化合物3-1(35克,70%)。
化合物3-2的制备
将化合物3-1(35克,108.6毫摩尔)溶解于THF(600毫升)之后,在-78℃下向反应混合物中添加正-BuLi(52毫升,130.35毫摩尔,2.5M的己烷溶液),并将反应混合物搅拌1小时。在室温下搅拌反应混合物12小时并向反应混合物中缓慢加入B(Oi-Pr)3(37毫升,162.9毫摩尔),且缓慢升高温度。用EA提取得到的有机层后,用无水MgSO4干燥以去除残余部分,减压蒸馏以去除溶剂,并与EA和己烷重结晶以得到化合物3-2(25克,81%).
化合物3-3的制备
将化合物3-2(10克,34.82毫摩尔)、2.4-二氯嘧啶(7.7克,52.24毫摩尔)、Pd(PPh3)4(1.6克,1.39毫摩尔)、2M Na2CO3(45毫升)、甲苯(150毫升)和乙醇(45毫升)混合后,在减压条件下搅拌该反应混合物。12小时后,将该混合物冷却至室温,向其中添加蒸馏水,随后用EA提取该反应混合物。用无水MgSO4干燥得到的有机层以去除残留水分,减压蒸馏以去除溶剂,并通过柱过滤以得到化合物3-3(11克,89%)。
化合物C-105的制备
将化合物2-2(5克,18.29毫摩尔)和化合物3-3(7.8克,21.94毫摩尔)溶解于DMF(150毫升)中之后,向混合物中缓慢加入NaH(1.09克,27.43毫摩尔,60%的矿物油溶液),并在室温下搅拌12小时。然后,将MeOH添加到该反应混合物。将所得固体在减压下进行过滤,用EA和DMF进行重结晶,得到化合物C-105(6.5克,60%)。
MS/FAB的实测值593;计算值592.71
实施例4:化合物C-111的制备
化合物4-1的制备
将1-溴-2-硝基苯(44克,0.21摩尔)、二苯并[b,d]呋喃-4-基硼酸(40克,0.18摩尔)、Pd(PPh3)4(10.3克,0.008摩尔)、K2CO3(72克,0.53摩尔)、甲苯(880毫升)、EtOH(300毫升)、和蒸馏水(300毫升)混合后,在120℃下将反应混合物搅拌12小时。反应终止后,用EA提取反应混合物。用MgSO4干燥所得有机层,过滤、减压蒸馏以去除溶剂,并通过柱过滤后得到化合物4-1(43克,85%)。
化合物4-2的制备
将化合物4-1(43克,0.15摩尔)、P(OEt)3(400毫升,0.4M)和亚磷酸三乙酯(400毫升)混合之后,将该反应混合物在90℃下搅拌12小时。终止反应之后,蒸馏该反应混合物以除去亚磷酸三乙酯,并通过柱过滤得到化合物4-2(30克,78%)。
化合物C-111的制备
将NaH60%(0.88克,0.022摩尔)溶解在DMF(100毫升)中后,搅拌溶液。将化合物4-2(4.34克,0.016摩尔)溶解在DMF(50毫升)中后,将该溶液添加至NaH溶液中,并搅拌1小时。将化合物1-3(6克,0.16摩尔)溶解在DMF(50毫升)中后,搅拌该溶液。然后,将化合物4-2的混合溶液添加到化合物1-3的混合溶液,并搅拌12小时。终止反应后,过滤所得黄色固体,并重结晶得到化合物C-111(1.6克,18%)。
MS/FAB的实测值577;计算值576.64
实施例5:化合物C-116的制备
化合物5-1的制备
将二苯并[b,d]噻吩-4-基硼酸(41克,181毫摩尔)、1.3-二溴硝基苯71克,254.5毫摩尔)、2M Na2CO3水溶液(270毫升)、甲苯(900毫升)和乙醇(300毫升)混合后,回流搅拌该反应混合物。5小时后,将该混合物冷却至室温,向其中添加蒸馏水,随后用EA提取该反应混合物。用无水MgSO4干燥得到的有机层以去除残留水分,减压蒸馏以去除溶剂,并通过柱过滤以得到化合物5-1(34克,35%)。
化合物5-2的制备
将化合物5-1(34克,89.52毫摩尔)、亚磷酸三乙酯(350毫升)和1,2-二氯苯(350毫升)混合后,在150℃下将反应混合物搅拌12小时。终止反应后,将反应混合物冷却至室温,减压蒸馏除去溶剂,并用EA重结晶以得到化合物5-2(11克,35%)。
化合物5-3的制备
将化合物5-2(7克,25.60毫摩尔)、碘苯(10.44克,51.21毫摩尔)、CuI(2.5克,12.80毫摩尔)、K3PO4(16.30克,76.82毫摩尔)和甲苯(200毫升)混合后,将反应混合物加热至50℃,加入乙二胺(1.72毫升,25.60毫摩尔),将该反应混合物回流搅拌12小时。将该反应混合物冷却至室温,用EA萃取,用NaHCO3水溶液清洗,用MgSO4干燥,过滤,并减压蒸馏以去除溶剂,并通过柱过滤以获得化合物5-3(8克,89%)。
化合物C-116的制备
将NaH(216毫克)溶解在DMF(30毫升)中后,搅拌溶液。将化合物5-3(3.5克,10.015毫摩尔)溶解在DMF(20毫升)中后,将该溶液添加至上述NaH溶液中,并搅拌1小时。将化合物1-3(4.3克,12.0189毫摩尔)溶解在DMF(20毫升)中后,搅拌该溶液。然后,将化合物5-3的混合溶液添加到化合物1-3的混合溶液,并搅拌12小时。终止反应后,过滤所得黄色固体,并重结晶得到化合物C-116(12克,60%)。
MS/FAB的实测值669;计算值668.81
实施例6:化合物C-118的制备
化合物6-1的制备
将2,5-二溴硝基苯(30克,106.8毫摩尔)、二苯并噻吩-4-基硼酸(20.3克,88.9毫摩尔)、Pd(PPh3)4(5.1克,4.45毫摩尔)、Na2CO3(27.9克,267毫摩尔)、甲苯(600毫升)和EtOH(100毫升)混合后,在90℃下将反应混合物搅拌3小时。搅拌后,加入纯净水,并用EA提取该反应混合物。用MgSO4干燥得到的有机层以去除残留水分,减压蒸馏以去除溶剂,并通过柱过滤以得到化合物6-1(24克,59%)。
化合物6-2的制备
将化合物6-1(23克,59.85毫摩尔)、苯基硼酸(8.8克,71.83毫摩尔)、Pd(PPh3)4(3.46克,2.99毫摩尔)、Na2CO3(19克,179.5毫摩尔)、甲苯(180毫升)和EtOH(90毫升)混合后,在120℃下将反应混合物搅拌3小时。搅拌后,加入纯净水,并用EA提取该反应混合物。用MgSO4干燥得到的有机层以去除残留水分,减压蒸馏以去除溶剂,并通过柱过滤以得到化合物6-2(22克,96%)。
化合物6-3的制备
将化合物6-2(15克,39.3毫摩尔)、和亚磷酸三乙酯(150毫升)混合后,在150℃下搅拌反应混合物24小时。搅拌后,用蒸馏装置将残留溶剂去除,并将反应混合物通过柱过滤得到化合物6-3(6克,46%)。
化合物C-118的制备
将NaH(600毫克,18.1毫摩尔)溶解在DMF(30毫升)中后,搅拌溶液。将化合物6-3(5克,14.3毫摩尔)溶解在DMF(30毫升)中后,将该溶液添加至上述NaH溶液中,并搅拌1小时。将化合物1-3(4.3克,11.9毫摩尔)溶解在DMF(30毫升)中后,搅拌该溶液。然后,将化合物6-3的混合溶液添加到化合物1-3的混合溶液,并在室温下搅拌24小时。终止反应后,过滤所得固体,并用EA洗涤,和通过柱过滤,得到化合物C-118(1.8克,23%)。
MS/FAB的实测值669;计算值668.81
实验实施例1:使用根据本发明的化合物的OLED器件的制造
使用本发明的化合物来制造OLED器件。用三氯乙烯、丙酮、乙醇和蒸馏水依次对用于有机发光二极管(OLED)器件(韩国三星康宁公司(SamsungCorning,Republic of Korea))的玻璃基材上的透明电极氧化铟锡(ITO)薄膜(15欧姆/平方)进行超声清洗,然后储存在异丙醇中。接着,将ITO基材安装在真空气相沉积设备的基材夹具(holder)上。将N1,N1’-([1,1’-联苯]-4,4’-二基)二(N1-(萘-1-基)-N4,N4-二苯基苯-1,4-二胺)引入所述真空气相沉积设备的室中,然后对所述设备的室压进行控制以达到10-6托(torr)。接着,向所述室施加电流以蒸发上述引入的物质,从而在ITO基材上形成厚度为60纳米的空穴注入层。然后,将N,N’-二(4-联苯基)-N,N’-二(4-联苯基)-4,4’-二氨基联苯引入所述真空气相沉积设备的另一个室中,通过向该室施加电流以进行蒸发,从而在所述空穴注入层上形成厚度为20纳米的空穴传输层。之后,将化合物C-40引入真空气相沉积设备的一个室中作为基质材料,并将化合物D-5引入另一个室中作为掺杂剂。将两种材料以不同的速率进行蒸发,并以15重量%的掺杂量进行沉积,以在空穴传输层上形成厚度为30纳米的发光层。然后,将2-(4-(9,10-二(萘-2-基)蒽-2-基)苯基)-1-苯基-1H-苯并[d]咪唑引入一个室中,并将喹啉合锂引入另一个室中。将两种物质以相同的速率进行蒸发,并以50重量%的掺杂量进行沉积,以在发光层上形成厚度为30纳米的电子传输层。然后,在电子传输层上沉积了厚度为2纳米的喹啉合锂作为电子注入层之后,通过另一真空气相沉积设备在电子注入层上沉积厚度为150纳米的Al阴极。从而,制备了OLED器件。制备OLED器件所用的所有材料,在使用前通过在10-6托条件下的真空升华进行纯化。
制备的OLED器件在3.9V的驱动电压下发射出亮度为1110坎德拉/平方米的绿光且电流密度为2.33毫安/平方厘米。
实验实施例2:使用根据本发明的化合物的OLED器件的制造
使用与实施例1相同的方法制备OLED器件,不同之处在于使用化合物C-94作为基质材料,使用化合物D-5作为掺杂剂。制备的OLED器件在3.9V的驱动电压下发射出亮度为1110坎德拉/平方米的绿光且电流密度为2.08毫安/平方厘米。
实验实施例3:使用根据本发明的化合物的OLED器件的制造
使用与实施例1相同的方法制备OLED器件,不同之处在于使用化合物C-105作为基质材料,使用化合物D-34作为掺杂剂。制备的OLED器件在4.0V的驱动电压下发射出亮度为1170坎德拉/平方米的绿光且电流密度为2.53毫安/平方厘米。
实验实施例4:使用根据本发明的化合物的OLED器件的制造
使用与实施例1相同的方法制备OLED器件,不同之处在于使用化合物C-111作为基质材料,使用化合物D-5作为掺杂剂。制备的OLED器件在4.2V的驱动电压下发射出亮度为1150坎德拉/平方米的绿光且电流密度为2.12毫安/平方厘米。
实验实施例5:使用根据本发明的化合物的OLED器件的制造
使用与实施例1相同的方法制备OLED器件,不同之处在于使用化合物C-118作为基质材料,使用化合物D-5作为掺杂剂。制备的OLED器件在3.8V的驱动电压下发射出亮度为1090坎德拉/平方米的橙色光且电流密度为2.22毫安/平方厘米。
比较例1:使用常规电致发光化合物制造OLED器件
使用与实施例1相同的方法来制备OLED器件,不同之处在于,通过使用4,4’-N,N’-二咔唑-联苯作为基质材料并使用化合物D-5作为掺杂剂,在空穴传输层上沉积厚度为30纳米的发光层,通过使用二(2-甲基-8-羟基喹啉合(quinolinato))4-苯基苯酚铝(III)沉积厚度为10纳米的空穴阻挡层。
制备的OLED器件在4.9V的驱动电压下发射出亮度为1000坎德拉/平方米的绿光且电流密度为2.86毫安/平方厘米。
本发明的电致发光化合物比常规材料具有更为优异的发光特性。此外,采用本发明的化合物作为绿光或橙色光发光基质材料的器件不仅具有优异的发光特性,而且通过降低驱动电压使功率效率增大。
Claims (6)
1.一种以下述通式1表示的化合物:
其中
L1和L2各自独立地表示单键、取代或未取代的3元至30元杂亚芳基、取代或未取代的(C6-C30)亚芳基或者取代或未取代的(C3-C30)环亚烷基;
X1和X2表示CH或N;
Y1和Y2各自独立地表示-O-、-S-、-CR5R6-或-NR7-,前提是Y1和Y2不同时存在;
Ar表示氢、氘、卤素、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、取代或未取代的3元-30元杂芳基,或N-咔唑基;
R1至R4各自独立地表示氢、氘、卤素、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、取代或未取代的3元至30元杂芳基、取代或未取代的(C3-C30)环烷基、取代或未取代的5元至7元杂环烷基、取代或未取代的(C6-C30)芳基(C1-C30)烷基、-NR11R12、-SiR13R14R15、-SR16、-OR17、氰基、硝基或羟基;或者它们与相邻取代基相连以形成单环或多环,(C5-C30)脂环或芳环,其碳原子可以被至少一个选自氮、氧和硫的杂原子替代;
R5至R7和R11至R17各自独立地表示氢、氘、卤素、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、取代或未取代的3元至30元杂芳基;取代或未取代的5元至7元杂环烷基、或取代或未取代的(C3-C30)环烷基;或者它们与相邻取代基相连以形成单环或多环,(C5-C30)脂环或芳环,其碳原子可以被至少一个选自氮、氧和硫的杂原子代替;
a、b、c和d各自独立地表示1-4的整数;当a、b、c或d是大于或等于2的整数时,每一个R1、每一个R2、每一个R3或每一个R4是相同或不同的;以及
所述杂环烷基、杂亚芳基、和杂芳基含有至少一个选自B、N、O、S、P(=O)、Si和P的杂原子。
2.如权利要求1所述的化合物,其特征在于,所述L1、L2、Ar、R1至R7以及R11至R17基团中所述取代的烷基、取代的(亚)芳基、取代的杂(亚)芳基、取代的环(亚)烷基、取代的杂环烷基和取代的芳烷基的取代基各自独立地是至少一种选自下组的基团:氘;卤素;未取代的或被卤素取代的(C1-C30)烷基;(C6-C30)芳基;未取代的或用(C1-C30)烷基或(C6-C30)芳基取代的3元至30元杂芳基;(C3-C30)环烷基;5元至7元杂环烷基;三(C1-C30)烷基甲硅烷基;三(C6-C30)芳基甲硅烷基;二(C1-C30)烷基(C6-C30)芳基甲硅烷基;(C1-C30)烷基二(C6-C30)芳基甲硅烷基;(C2-C30)烯基;(C2-C30)炔基;氰基;N-咔唑基;二(C1-C30)烷基氨基;二(C6-C30)芳基氨基;(C1-C30)烷基(C6-C30)芳基氨基;二(C6-C30)芳基硼羰基;二(C1-C30)烷基硼羰基;(C6-C30)芳基(C1-C30)烷基;(C1-C30)烷基(C6-C30)芳基硼羰基;(C1-C30)烷基(C6-C30)芳基;羧基;硝基和羟基。
4.如权利要求1所述的化合物,其特征在于,
L1和L2各自独立地代表单键、3元至30元杂亚芳基、或(C6-C30)亚芳基;
X1和X2各自独立地表示CH或N;
Y1和Y2各自独立地表示-O-、-S-、-CR5R6-或–NR7-,前提是Y1和Y2不同时存在;
Ar表示氢、氘、卤素、(C1-C30)烷基、(C6-C30)芳基、3元至30元杂芳基、或N-咔唑基;
R1至R4各自独立地表示氢、氘、卤素、(C1-C30)烷基、(C6-C30)芳基、3元至30元杂芳基、N-咔唑基、或-SiR13R14R15;
R5至R7各自独立地表示(C1-C30)烷基、(C6-C30)芳基、或3元至30元杂芳基;或者R5和R6相互结合以形成单环或多环,(C5-C30)脂环或芳环,其碳原子可以被至少一个选自氮、氧和硫的杂原子代替;
R13至R15各自独立地表示(C1-C30)烷基、(C6-C30)芳基、或3元至30元杂芳基;以及
L1和L2中的亚芳基和杂亚芳基,Ar中的烷基、芳基、杂芳基和N-咔唑基,R1至R4中的烷基、芳基、杂芳基和N-咔唑基,R5至R7和R13至R15中的烷基、芳基和杂芳基可被至少一个选自下组的基团取代:氘;卤素;未取代或被卤素取代的(C1-C30)烷基;(C6-C30)芳基;未取代或者被(C1-C30)烷基或(C6-C30)芳基取代的3元至30元杂芳基;(C3-C30)环烷基;N-咔唑基;二(C1-C30)烷基氨基;二(C6-C30)芳基氨基;(C1-C30)烷基(C6-C30)芳基氨基;(C6-C30)芳基(C1-C30)烷基;和(C1-C30)烷基(C6-C30)芳基。
6.一种包含如权利要求1所述的化合物的有机电致发光器件。
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Also Published As
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KR20130011405A (ko) | 2013-01-30 |
JP2014525910A (ja) | 2014-10-02 |
TW201307336A (zh) | 2013-02-16 |
WO2013012297A1 (en) | 2013-01-24 |
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