CN103857680A - 新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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- CN103857680A CN103857680A CN201280049555.4A CN201280049555A CN103857680A CN 103857680 A CN103857680 A CN 103857680A CN 201280049555 A CN201280049555 A CN 201280049555A CN 103857680 A CN103857680 A CN 103857680A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 63
- 125000003118 aryl group Chemical group 0.000 claims description 60
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 41
- 229910052736 halogen Inorganic materials 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 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 22
- 229910052805 deuterium Inorganic materials 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 125000001118 alkylidene group Chemical group 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 238000005401 electroluminescence Methods 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000004450 alkenylene group Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- 125000002723 alicyclic group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000005104 aryl silyl group Chemical group 0.000 claims description 8
- 125000002769 thiazolinyl 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
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000001769 aryl 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
- 229910052796 boron Inorganic materials 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
- 125000003282 alkyl amino group Chemical group 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
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 238000002425 crystallisation Methods 0.000 abstract description 2
- 230000008025 crystallization Effects 0.000 abstract description 2
- 239000002585 base Substances 0.000 description 105
- -1 isobutyl- Chemical group 0.000 description 93
- 239000010410 layer Substances 0.000 description 38
- 239000000463 material Substances 0.000 description 33
- 239000002019 doping agent Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 0 C*1(C2C=C(C=CC=C3)C3=CC2)C2=C=CC=C2c2ccccc12 Chemical compound C*1(C2C=C(C=CC=C3)C3=CC2)C2=C=CC=C2c2ccccc12 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 230000008021 deposition Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom 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
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 4
- 229910052741 iridium Inorganic materials 0.000 description 4
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 239000011368 organic material Substances 0.000 description 4
- 125000005561 phenanthryl group Chemical group 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- 150000004646 arylidenes Chemical group 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
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 229910052731 fluorine Inorganic materials 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
- 125000001715 oxadiazolyl group Chemical group 0.000 description 3
- 125000002971 oxazolyl group Chemical group 0.000 description 3
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 3
- 239000008213 purified water Substances 0.000 description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 3
- 230000027756 respiratory electron transport chain Effects 0.000 description 3
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 3
- 125000004169 (C1-C6) alkyl 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
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-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
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-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
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-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
- 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 2
- 239000002253 acid Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 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
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 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
- 125000004956 cyclohexylene group Chemical group 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 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
- 125000005956 isoquinolyl group Chemical group 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 2
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 2
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- 239000011574 phosphorus Substances 0.000 description 2
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- 125000004076 pyridyl group Chemical group 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
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- 239000000377 silicon dioxide Substances 0.000 description 2
- 229960001866 silicon dioxide Drugs 0.000 description 2
- 238000003756 stirring Methods 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
- JWJQEUDGBZMPAX-UHFFFAOYSA-N (9-phenylcarbazol-3-yl)boronic acid Chemical compound C12=CC=CC=C2C2=CC(B(O)O)=CC=C2N1C1=CC=CC=C1 JWJQEUDGBZMPAX-UHFFFAOYSA-N 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 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
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 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
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical class CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
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- 229910003564 SiAlON Inorganic materials 0.000 description 1
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 1
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- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000004653 anthracenylene group Chemical group 0.000 description 1
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- 230000009286 beneficial effect Effects 0.000 description 1
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- 125000005605 benzo group Chemical group 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
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- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000005382 boronyl group Chemical group 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZPFKRQXYKULZKP-UHFFFAOYSA-N butylidene Chemical group [CH2+]CC[CH-] ZPFKRQXYKULZKP-UHFFFAOYSA-N 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 150000004770 chalcogenides Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
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- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
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- 239000012153 distilled water Substances 0.000 description 1
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- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
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- 125000000524 functional group Chemical group 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- RTRAMYYYHJZWQK-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1 RTRAMYYYHJZWQK-UHFFFAOYSA-N 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 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 1
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- 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
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
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- 229910052763 palladium Inorganic materials 0.000 description 1
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- VXPCQISYVPFYRK-UHFFFAOYSA-N profenamine hydrochloride Chemical compound Cl.C1=CC=C2N(CC(C)N(CC)CC)C3=CC=CC=C3SC2=C1 VXPCQISYVPFYRK-UHFFFAOYSA-N 0.000 description 1
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- 125000002098 pyridazinyl group Chemical group 0.000 description 1
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- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 1
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- 229920006395 saturated elastomer Polymers 0.000 description 1
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- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000243 solution Substances 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
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
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- 238000004506 ultrasonic cleaning 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
本发明涉及新颖的有机电致发光化合物以及含有该化合物的有机电致发光器件。由于本发明的有机电致发光化合物具有高传输电子效率,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提高的功率效率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.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,从电致发光机理来看,磷光材料理论上能显示出比荧光材料高4倍的发光效率。因此,近年来,人们已经对磷光材料进行了研究。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(4,6-二氟苯基吡啶根合-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,已知具有高效率的有机EL器件使用浴铜灵(BCP)或二(2-甲基-8-羟基喹啉合(quinolinate))(4-苯基苯酚)铝(III)(BAlq)用于空穴阻挡层;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。
虽然这些磷光物质基质材料提供良好的发光特征,它们具有下述不足:(1)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。(2)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,因此应当采取较高的功率效率从而降低功耗。虽然包含磷光材料的有机EL器件提供比包含荧光材料的有机EL器件更高的电流效率(cd/A),但是当常规材料例如BAlq或CBP用作磷光基质材料时,相比采用荧光材料的有机EL器件,必须采用高得多的驱动电压。因此,对于功率效率(lm/W)而言没有可取之处。(3)此外,有机EL器件的工作寿命较短,并且仍然需要改善发光效率。
国际专利公开第WO2006/049013号揭示了用于有机电致发光材料的化合物,所述化合物具有稠合双环基团作为骨架结构。但是,该文献没有揭示具有与咔唑基团一起的含氮稠合双环基团的化合物,该咔唑基团与和芳环稠合的杂环烷基或环烷基稠合。
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,该化合物具有优异的结构,使得器件具有高发光效率和长工作寿命并具有合适的色坐标;本发明还提供了一种采用所述化合物的有机电致发光器件,其具有高效率和长寿命。
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表示的有机电致发光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表示CH或N;
Y1和Y2各自独立地表示-O-、-S-、-CR6R7-或-NR8-;
R1至R5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R4和R5各自独立地通过取代或未取代的(C3-C30)亚烷基或取代或未取代的(C3-C30)亚烯基与相邻取代基相连以形成单环或多环的脂环或芳环,其碳原子可以被至少一个选自氮、氧和硫的杂原子代替;
R6至R8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;或者它们通过取代或未取代的(C3-C30)亚烷基或取代或未取代的(C3-C30)亚烯基与相邻取代基相连以形成单环或多环的脂环或芳环,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e各自独立地表示1-4的整数,当a、b、c或e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R5是相同或不同的;
d表示1-3的整数;当d是大于或等于2的整数时,每一个R4是相同或不同的;以及
所述杂环烷基和杂(亚)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,由于本发明的有机电致发光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提高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。
本发明涉及用上述通式1表示的化合物,包括所述化合物的有机电致发光材料,以及包括所述材料的有机电致发光器件。
本文中,“(C1-C30)(亚)烷基”是指具有1-30个碳原子的线型或支化的(亚)烷基,所述碳原子数优选为1-20,更优选为1-10,所述(亚)烷基包括但不限于:甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基等。
本文中,“(C2-C30)(亚)烯基”是指具有2-30个碳原子的线型或支化的(亚)烯基,所述碳原子数优选为2-20,更优选为2-10,所述(亚)烯基包括但不限于: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。
本文中,“(C2-C30)(亚)炔基”是指具有2-30个碳原子的线型或支化的(亚)炔基,所述碳原子数优选为2-20,更优选为2-10,所述(亚)炔基包括但不限于: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。
本文中,(“C1-C30)烷氧基”是指具有1-30个碳原子的线型或支化的烷氧基,所述碳原子数优选为1-20,更优选为1-10,所述烷氧基包括但不限于:甲氧基、乙氧基、丙氧基、异丙氧基、1-乙基丙氧基等。
本文中,“(C3-C30)环烷基”是指具有3-30个碳原子的单环或多环烃,所述碳原子数优选为3-20,更优选为3-7,所述环烷基包括但不限于:环丙基、环丁基、环戊基、环己基等。
本文中,“(C3-C30)环亚烷基”是指通过从具有3-30个(优选3-20个,更优选3-7个)碳原子的环烷基中去除一个氢得到的基团。
本文中,“5元至7元杂环烷基”是指具有至少一个选自B、N、O、S、P(=O)、Si和P(优选选自N、O和S)的杂原子、有5-7个骨架原子的环烷基,所述杂环烷基包括但不限于:四氢呋喃、吡咯烷、四氢噻吩(thiolan)、四氢吡喃等。
本文中,“卤素”包括F、Cl、Br和I。
本文中,“(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,所述碳原子数优选为6-20,更优选为6-12,所述(亚)芳基包括但不限于: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、芘基、并四苯基(tetracenyl)、苝基(perylenyl)、基(chrysenyl)、萘并萘基(naphthacenyl)、荧蒽基(fluoranthenyl)等。所述萘基包括1-萘基、2-萘基等;所述蒽基包括1-蒽基、2-蒽基、9-蒽基等;所述菲基包括1-菲基、2-菲基、3-菲基、4-菲基、9-菲基等;所述萘并萘基包括1-萘并萘基、2-萘并萘基、9-萘并萘基等;所述芘基包括1-芘基、2-芘基、4-芘基等;所述联苯基包括2-联苯基、3-联苯基、4-联苯基等;所述三联苯基包括对-三联苯基-4-基、对-三联苯基-3-基、对-三联苯基-2-基、间-三联苯基-4-基、间-三联苯基-3-基、间-三联苯基-2-基等;所述芴基包括1-芴基、2-芴基、3-芴基、4-芴基、9-芴基等。
本文中,“3元至30元杂(亚)芳基”是指具有至少一个、优选1-4个杂原子和3-30个环骨架原子的芳基,所述杂原子选自B、N、O、S、P(=O)、Si和P;其是单环或与至少一个苯环稠和的稠环;其优选具有5-21个,更优选具有5-12个环骨架原子;其可以是部分饱和的;其可以将至少一个杂芳基或芳基基团与杂芳基通过单键连接形成。所述杂(亚)芳基包括二价芳基,其环中的杂原子可被氧化或季铵化,以形成N-氧化物、季铵盐等。所述杂(亚)芳基包括但不限于:单环环型杂芳基,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、异噁唑基、噁唑基、噁二唑基、三嗪基、四嗪基、***基、四唑基、呋咱基(furazanyl)、吡啶基、吡嗪基、嘧啶基、哒嗪基等;稠和的环型杂芳基,包括苯并呋喃基(benzofuranyl)、苯并噻吩基、二苯并呋喃基、二苯并噻吩基、异苯并呋喃基、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、菲啶基(phenanthridinyl)、苯并间二氧杂环戊烯基(benzodioxolyl)、吖啶基、菲咯啉基(phenanthrolinyl)、吩嗪基、吩噻嗪基、吩噁嗪基等;及其N-氧化物(例如吡啶基N-氧化物、喹啉基N-氧化物);或其季铵盐等。吡咯基包括:1-吡咯基、2-吡咯基和3-吡咯基等;吡啶基包括2-吡啶基、3-吡啶基、4-吡啶基等;吲哚基包括1-吲哚基、2-吲哚基、3-吲哚基、4-吲哚基、5-吲哚基、6-吲哚基、7-吲哚基等;异吲哚基包括1-异吲哚基、2-异吲哚基、3-异吲哚基、4-异吲哚基、5-异吲哚基、6-异吲哚基、7-异吲哚基等;呋喃基包括2-呋喃基、3-呋喃基等;苯并呋喃基包括2-苯并呋喃基、3-苯并呋喃基、4-苯并呋喃基、5-苯并呋喃基、6-苯并呋喃基、7-苯并呋喃基等;异苯并呋喃基包括1-异苯并呋喃基、3-异苯并呋喃基、4-异苯并呋喃基、5-异苯并呋喃基、6-异苯并呋喃基、7-异苯并呋喃基等;喹啉基包括3-喹啉基、4-喹啉基、5-喹啉基、6-喹啉基、7-喹啉基、8-喹啉基等;异喹啉基包括1-异喹啉基、3-异喹啉基、4-异喹啉基、5-异喹啉基、6-异喹啉基、7-异喹啉基、8-异喹啉基等;喹喔啉基包括2-喹喔啉基、5-喹喔啉基、6-喹喔啉基等;咔唑基包括1-咔唑基、2-咔唑基、3-咔唑基、4-咔唑基、9-咔唑基等;菲啶基包括1-菲啶基、2-菲啶基、3-菲啶基、4-菲啶基、6-菲啶基、7-菲啶基、8-菲啶基、9-菲啶基、10-菲啶基等;吖啶基包括1-吖啶基、2-吖啶基、3-吖啶基、4-吖啶基、9-吖啶基等;菲咯啉基包括1,7-菲咯啉-2-基、1,7-菲咯啉-3-基、1,7-菲咯啉-4-基、1,7-菲咯啉-5-基、1,7-菲咯啉-6-基、1,7-菲咯啉-8-基、1,7-菲咯啉-9-基、1,7-菲咯啉-10-基、1,8-菲咯啉-2-基、1,8-菲咯啉-3-基、1,8-菲咯啉-4-基、1,8-菲咯啉-5-基、1,8-菲咯啉-6-基、1,8-菲咯啉-7-基、1,8-菲咯啉-9-基、1,8-菲咯啉-10-基、1,9-菲咯啉-2-基、1,9-菲咯啉-3-基、1,9-菲咯啉-4-基、1,9-菲咯啉-5-基、1,9-菲咯啉-6-基、1,9-菲咯啉-7-基、1,9-菲咯啉-8-基、1,9-菲咯啉-10-基、1,10-菲咯啉-2-基、1,10-菲咯啉-3-基、1,10-菲咯啉-4-基、1,10-菲咯啉-5-基、2,9-菲咯啉-1-基、2,9-菲咯啉-3-基、2,9-菲咯啉-4-基、2,9-菲咯啉-5-基、2,9-菲咯啉-6-基、2,9-菲咯啉-7-基、2,9-菲咯啉-8-基、2,9-菲咯啉-10-基、2,8-菲咯啉-1-基、2,8-菲咯啉-3-基、2,8-菲咯啉-4-基、2,8-菲咯啉-5-基、2,8-菲咯啉-6-基、2,8-菲咯啉-7-基、2,8-菲咯啉-9-基、2,8-菲咯啉-10-基、2,7-菲咯啉-1-基、2,7-菲咯啉-3-基、2,7-菲咯啉-4-基、2,7-菲咯啉-5-基、2,7-菲咯啉-6-基、2,7-菲咯啉-8-基、2,7-菲咯啉-9-基、2,7-菲咯啉-10-基等;吩嗪基包括1-吩嗪基、2-吩嗪基等;吩噻嗪基包括1-吩噻嗪基、2-吩噻嗪基、3-吩噻嗪基、4-吩噻嗪基、10-吩噻嗪基等;吩噁嗪基包括1-吩噁嗪基、2-吩噁嗪基、3-吩噁嗪基、4-吩噁嗪基、10-吩噁嗪基等;噁唑基包括2-噁唑基、4-噁唑基、5-噁唑基等;噁二唑基包括2-噁二唑基、5-噁二唑基等;呋咱基包括3-呋咱基等;二苯并呋喃基包括1-二苯并呋喃基、2-二苯并呋喃基、3-二苯并呋喃基、4-二苯并呋喃基等;二苯并噻吩基包括1-二苯并噻吩基、2-二苯并噻吩基、3-二苯并噻吩基、4-二苯并噻吩基等。
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。
L1、L2、R1至R8以及R11至R17基团中取代的(亚)烷基、取代的烯基、取代的环(亚)烷基、取代的杂环烷基、取代的(亚)芳基、取代的杂(亚)芳基、取代的芳烷基和取代的芳环的取代基各自独立地优选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、3元至30元杂芳基、被(C1-C30)烷基取代的3元至30元杂芳基、被(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)芳基硼基(boronyl)、二(C1-C30)烷基硼基、(C1-C30)烷基(C6-C30)芳基硼基、(C6-C30)芳基(C1-C30)烷基、(C1-C30)烷基(C6-C30)芳基、羧基、硝基和羟基;更优选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-C20)烷基和(C6-C20)芳基;更优选至少一种选自下组的基团:氘、氟、甲基、苯基和萘基。
具体的,在上述通式1中,L1和L2各地独立地表示单键、3元至30元杂亚芳基、(C6-C30)亚芳基、或(C6-C30)环亚烷基;X是CH或N;Y1和Y2各自独立地表示-O-、-S-、-CR6R7-或–NR8-;R1-R5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、-NR11R12或-SiR13R14R15;或R4和R5各自独立地通过(C3-C30)亚烷基或(C3-C30)亚烯基与相邻的取代基相连形成单环或多环的脂环或芳环,其碳原子可以被至少一个选自氮、氧和硫的杂原子替代;R6-R8各自独立地表示氢、氘、卤素、(C1-C30)烷基、(C6-C30)芳基、或3元至30元杂芳基;R11-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;L1和L2中的亚芳基、杂亚芳基和环亚烷基、R1-R8和R11-R15中的烷基、芳基、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、(C1-C30)烷基(C6-C30)芳基、3元至30元杂芳基、被(C6-C30)芳基取代的3元至30元杂芳基、(C3-C30)环烷基和(C6-C30)芳基(C1-C30)烷基。
在上述通式1中,L1和L2各自独立地优选是单键、环亚丙基、环亚丁基、环亚戊基、环亚己基、环亚庚基、环亚辛基、亚苯基、甲基亚苯基、亚萘基、亚联苯基、亚三联苯基、亚蒽基、亚茚基、亚芴基、亚菲基、亚苯并[9,10]菲基、亚芘基、亚苯基烯基(phenylenylene)、亚基、亚并四苯基、荧蒽基、亚呋喃基、亚噻吩基、亚吡咯基、亚咪唑基、亚吡唑基、亚噻唑基、亚噻二唑基、亚异噻唑基、亚异噁唑基、亚噁唑基、亚噁二唑基、亚三嗪基、亚四嗪基、亚***基、亚呋咱基、亚吡啶基、亚吡嗪基、亚嘧啶基、亚哒嗪基、亚苯并呋喃基、亚苯并噻吩基、亚异苯并呋喃基、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、亚异吲哚基、亚吲哚基、亚吲唑基、亚苯并噻二唑基、亚喹啉基、亚异喹啉基、亚噌啉基、亚喹唑啉基、亚喹喔啉基、亚咔唑基、亚菲啶基、亚苯并间二氧杂环戊烯基、亚二苯并呋喃基和亚二苯并噻吩基,L1和L2被至少一个选自下组的基团取代:氘、卤素、未取代的或被卤素取代的(C1-C30)烷基、(C6-C30)芳基、(C1-C30)烷基(C6-C30)芳基、3元至30元杂芳基、被(C6-C30)芳基取代的3元至30元杂芳基、(C3-C30)环烷基和(C6-C30)芳基(C1-C30)烷基。更优选地,在上述通式1中,L1和L2各自独立地选自单键、亚苯基、甲基亚苯基和环亚己基。
在上述通式1中,Y1和Y2各自独立地选自以下结构:
在以上通式1中,R1至R5各自独立地优选为(C6-C20)芳基、5元至21元杂芳基、-NR11R12或-SiR13R14R15;或者它们通过取代或未取代的(C3-C30)亚烷基或取代或未取代的(C3-C30)亚烯基与相邻取代基相连以形成单环或多环的脂环或芳环,更优选为苯基、咔唑基、二苯基氨基或甲基二苯基甲硅烷基;或者它们通过取代或未取代的(C3-C30)亚烷基或取代或未取代的(C3-C30)亚烯基与相邻取代基相连以形成单环或多环的脂环或芳环。R11-R15各自独立地优选为(C1-C6)烷基或(C6-C20)芳基,更优选为甲基或苯基。
在上述通式1中,R6-R8各自独立地优选为氢、(C1-C6)烷基、取代或未取代的(C6-C20)芳基、或取代或未取代的5元至21元杂芳基,更优选为氢、甲基、苯基、联苯基、萘基、被氘取代的苯基、被氟取代的苯基、被甲基取代的芴基、或萘基苯基。
其中,L1、L2、X1、Y1、Y2、R1-R5、a、b、c、d和e如上述通式1所定义,Hal表示卤素。
此外,本发明提供包括通式1化合物的有机电致发光材料,以及包括所述材料的有机电致发光器件。上述材料可只包括本发明的有机电致发光化合物,或者还可包括通常用于有机电致发光材料的常规材料。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的有机电致发光化合物。此外,所述有机层包括发光层,在该发光层中包含通式1的有机电致发光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;以及
L101、L102和L103各自独立地选自下述结构:
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可通过(C3-C12)亚烷基或(C3-C12)亚烯基彼此相连以形成单环或多环的脂环或芳环;
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3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;
R231至R242各自独立地表示氢、氘、未取代或被卤素取代的(C1-C30)烷基、(C1-C30)烷氧基、卤素、取代或未取代的(C6-C30)芳基、氰基、或取代或未取代的(C5-C30)环烷基,或者每个R231至R242可通过(C2-C30)亚烷基或(C2-C30)亚烯基与相邻取代基相连以形成螺环或稠环,或者可通过(C2-C30)亚烷基或(C2-C30)亚烯基与R207或R208相连以形成饱和或不饱和的稠环。
通式2的掺杂剂包括以下这些,但不限于此:
除了通式1表示的有机电致发光化合物之外,本发明的有机电致发光器件还可包括至少一种选自基于芳胺的化合物和基于苯乙烯基芳胺的化合物的化合物。
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1族金属、第2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,除了本发明的有机电致发光化合物之外,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”)。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-18的制备
化合物1-1的制备
将2,4-二氯喹唑啉(50克,251毫摩尔)和二苯并[b,d]呋喃-4-基硼酸(53.2克,251毫摩尔)溶解于甲苯(1L)和纯化水(200mL)的混合物中之后,向该混合物中添加Pd(PPh3)4(14.5克,12.5毫摩尔)和Na2CO3(80克,755毫摩尔)。将该混合物在80℃下搅拌20小时。将该反应混合物冷却至室温,并用氯化铵水溶液(200毫升)终止反应。用1升的乙酸乙酯(EA)萃取反应混合物,并用二氯甲烷(1升)进一步萃取水性层。用无水硫酸镁干燥所得有机层,并减压去除有机溶剂。通过硅胶过滤所得固体,并在减压下除去溶剂。用EA(100毫升)洗涤所得固体,得到化合物1-1(50g,74%)。
化合物1-2的制备
将9-苯基-9H-咔唑-3-基硼酸(30克,149毫摩尔)、1-溴-2-硝基苯(51克,178.8毫摩尔)、K2CO3(52克,372.5毫摩尔)和Pd(PPh3)4(6.8克,5.8毫摩尔)溶解于甲苯(600毫升)、EtOH(150毫升)和纯化水(150毫升)的混合物中之后,将该反应混合物回流搅拌24小时。反应终止后,将反应混合物冷却至室温,通过重力分离从混合物中除去水性层。对得到的有机层进行浓缩,并用二氯甲烷(MC)进行研磨,然后过滤得到化合物1-2(50g,92%)。
化合物1-3的制备
将化合物1-2(50克,137毫摩尔)溶解于P(OEt)3(300毫升)和1,2-二氯苯(300毫升)的混合物中后,在150℃下将反应混合物搅拌24小时。反应终止后,将反应混合物减压浓缩并用EA萃取。然后,将所得的有机层进行浓缩,并通过二氧化硅柱进行纯化,得到化合物1-3(32g,70%)。
化合物C-18的制备
将化合物1-1(5.5克,16.5毫摩尔)和化合物1-3(5.0克,15毫摩尔)悬浮于80毫升二甲基甲酰胺(DMF)之后,在室温下向该混合物中加入60%NaH(930毫克,23.2毫摩尔)。搅拌该反应混合物12小时。在添加纯化水(1L)之后,对该混合物进行减压过滤。分别用MeOH/EA、DMF和EA/四氢呋喃(THF)对所得固体进行研磨。将该固体溶解于MC中并通过二氧化硅过滤。然后,用MeOH/EA研磨该固体以得到化合物C-18(4.6克,48.9%)。
MS/FAB的实测值627;计算值626.70
器件实施例1:使用本发明的有机电致发光化合物制备有机发光二极管
(OLED)器件
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OLED器件的玻璃基材上的透明电极氧化铟锡(ITO)薄膜(15Ω/sq)(韩国三星康宁公司(Samsung Corning,Republic of Korea))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N1N1’-([1,1’-联苯基]-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。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60nm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20nm的空穴传输层。之后,将化合物C-18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-7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4重量%掺杂剂(以基质材料和掺杂剂的总重量计)的掺杂量进行沉积,从而在空穴传输层上形成厚度为30nm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8-羟基喹啉合锂(lithium quinolate)引入另一个室中。将两种物质分别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30nm的电子传输层。然后,在电子传输层上沉积了厚度为1-2nm的8-羟基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150nm的Al阴极。从而,制备了OLED器件。
制备的OLED器件在5.6V的驱动电压下发射出亮度为3,400cd/m2的红光且电流密度为44.7mA/cm2。
比较例1:使用常规电致发光材料制造OLED器件
使用与器件实施例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(CBP)作为基质材料并使用化合物D-11作为掺杂剂,在空穴传输层上沉积发光层,通过使用二(2-甲基-8-羟基喹啉合(quinolinato))4-苯基苯酚铝(III),在发光层与电子传输层之间,沉积厚度为10nm的空穴阻挡层。
制备的OLED器件在8.2V的驱动电压下发射出亮度为1,000cd/m2的红光且电流密度为20.0mA/cm2。
Claims (6)
1.一种由以下通式1表示的有机电致发光化合物:
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表示CH或N;
Y1和Y2各自独立地表示-O-、-S-、-CR6R7-或-NR8-;
R1至R5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R4和R5各自独立地通过取代或未取代的(C3-C30)亚烷基或取代或未取代的(C3-C30)亚烯基与相邻取代基相连以形成单环或多环的脂环或芳环,其碳原子可以被至少一个选自氮、氧和硫的杂原子代替;
R6至R8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;或者它们通过取代或未取代的(C3-C30)亚烷基或取代或未取代的(C3-C30)亚烯基与相邻取代基相连以形成单环或多环的脂环或芳环,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e各自独立地表示1-4的整数,当a、b、c或e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R5是相同或不同的;
d表示1-3的整数;当d是大于或等于2的整数时,每一个R4是相同或不同的;以及
所述杂环烷基和杂(亚)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所述的有机电致发光化合物,其特征在于,所述L1和L2、R1至R8、R11至R17中所述取代的(亚)烷基、取代的烯基、取代的环(亚)烷基、取代的杂环烷基、取代的(亚)芳基、取代的杂(亚)芳基、取代的芳烷基和取代的芳环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、3元至30元杂芳基、被(C1-C30)烷基取代的3元至30元杂芳基、被(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)芳基硼基、二(C1-C30)烷基硼基、(C1-C30)烷基(C6-C30)芳基硼基、(C6-C30)芳基(C1-C30)烷基、(C1-C30)烷基(C6-C30)芳基、羧基、硝基和羟基。
3.如权利要求1所述的有机电致发光化合物,其特征在于,所述L1和L2各自独立地表示单键、3元至30元杂亚芳基、(C6-C30)亚芳基、或(C6-C30)环亚烷基;
X1是CH或N;
Y1和Y2各自独立地表示-O-、-S-、-CR6R7-或-NR8-;
R1至R5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、-NR11R12或-SiR13R14R15;或者R4和R5各自独立地通过(C3-C30)亚烷基或(C3-C30)亚烯基与相邻取代基相连以形成单环或多环的脂环或芳环,其碳原子可以被至少一个选自氮、氧和硫的杂原子代替;
R6至R8各自独立地表示氢、氘、卤素、(C1-C30)烷基、(C6-C30)芳基、或3元至30元杂芳基;
R11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
所述L1和L2中的亚芳基、杂亚芳基和环亚烷基,以及R1至R8和R11至R15中的烷基、芳基和杂芳基可以被至少一个选自下组的基团取代:氘、卤素、未取代的或被卤素取代的(C1-C30)烷基、(C6-C30)芳基、(C1-C30)烷基(C6-C30)芳基、3元至30元杂芳基、被(C6-C30)芳基取代的3元至30元杂芳基、(C3-C30)环烷基、以及(C6-C30)芳基(C1-C30)烷基。
6.一种包含权利要求1所述的有机电致发光化合物的有机电致发光器件。
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KR10-2011-0088684 | 2011-09-01 | ||
PCT/KR2012/007008 WO2013032284A1 (en) | 2011-09-01 | 2012-08-31 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
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CN112400010A (zh) * | 2018-07-25 | 2021-02-23 | 罗门哈斯电子材料韩国有限公司 | 有机电致发光化合物以及包含其的有机电致发光装置 |
CN111936491B (zh) * | 2018-04-17 | 2024-07-26 | Lt素材株式会社 | 杂环化合物以及包含此化合物的有机发光装置 |
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KR101618409B1 (ko) * | 2013-10-10 | 2016-05-04 | 주식회사 두산 | 유기 화합물 및 이를 포함하는 유기 전계 발광 소자 |
WO2016112762A1 (zh) * | 2015-01-13 | 2016-07-21 | 广州华睿光电材料有限公司 | 化合物、包含其的混合物、组合物和有机电子器件 |
US11495749B2 (en) | 2015-04-06 | 2022-11-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
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EP3960737B1 (en) * | 2017-03-27 | 2023-08-09 | Lg Chem, Ltd. | Benzocarbazole-based compounds and organic light-emitting device comprising them |
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US11834459B2 (en) | 2018-12-12 | 2023-12-05 | Universal Display Corporation | Host materials for electroluminescent devices |
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JP2006131519A (ja) * | 2004-11-04 | 2006-05-25 | Idemitsu Kosan Co Ltd | 縮合環含有化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
EP2080762B1 (en) * | 2006-11-09 | 2016-09-14 | Nippon Steel & Sumikin Chemical Co., Ltd. | Compound for organic electroluminescent device and organic electroluminescent device |
KR20120038060A (ko) * | 2010-10-13 | 2012-04-23 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR101531904B1 (ko) * | 2010-10-13 | 2015-06-29 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자 |
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KR20120132962A (ko) * | 2011-05-30 | 2012-12-10 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR20120136618A (ko) * | 2011-06-09 | 2012-12-20 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자 |
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CN110392682B (zh) * | 2017-03-28 | 2022-03-15 | 东丽株式会社 | 化合物、含有该化合物的电子器件、有机薄膜发光元件、显示装置及照明装置 |
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CN112400010A (zh) * | 2018-07-25 | 2021-02-23 | 罗门哈斯电子材料韩国有限公司 | 有机电致发光化合物以及包含其的有机电致发光装置 |
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