CN102933531A - 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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- CN102933531A CN102933531A CN2011800273959A CN201180027395A CN102933531A CN 102933531 A CN102933531 A CN 102933531A CN 2011800273959 A CN2011800273959 A CN 2011800273959A CN 201180027395 A CN201180027395 A CN 201180027395A CN 102933531 A CN102933531 A CN 102933531A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 70
- 239000000126 substance Substances 0.000 claims abstract description 17
- 125000001424 substituent group Chemical group 0.000 claims description 89
- 125000003118 aryl group Chemical group 0.000 claims description 58
- 239000010410 layer Substances 0.000 claims description 39
- -1 nitro, hydroxyl Chemical group 0.000 claims description 33
- 238000005401 electroluminescence Methods 0.000 claims description 30
- 150000002431 hydrogen Chemical class 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 26
- 229910052805 deuterium Inorganic materials 0.000 claims description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 24
- 125000002723 alicyclic group Chemical group 0.000 claims description 20
- 125000001118 alkylidene group Chemical group 0.000 claims description 20
- 239000012044 organic layer Substances 0.000 claims description 20
- 125000004450 alkenylene group Chemical group 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 16
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 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
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000011159 matrix material Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000005561 phenanthryl group Chemical group 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000001425 triazolyl group Chemical group 0.000 claims description 5
- 125000005104 aryl silyl group Chemical group 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 4
- 125000005605 benzo group Chemical group 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000000707 boryl group Chemical group B* 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 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 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 150000002602 lanthanoids Chemical class 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002524 organometallic group Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- 125000003968 arylidene group Chemical group [H]C(c)=* 0.000 claims 2
- 150000002739 metals Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 description 44
- 239000000203 mixture Substances 0.000 description 23
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 239000000758 substrate Substances 0.000 description 19
- 239000002585 base Substances 0.000 description 15
- 239000002019 doping agent Substances 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000012153 distilled water Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000000151 deposition Methods 0.000 description 9
- 230000008021 deposition Effects 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 239000006200 vaporizer Substances 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 5
- 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 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 229910052741 iridium Inorganic materials 0.000 description 4
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-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
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000000605 extraction 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
- 238000003756 stirring Methods 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 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
- 150000004646 arylidenes Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000004770 chalcogenides Chemical group 0.000 description 2
- 125000000259 cinnolinyl group Chemical class N1=NC(=CC2=CC=CC=C12)* 0.000 description 2
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000011368 organic material Substances 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
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 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
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 2
- QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 1
- ITZYPLMJTLJHGZ-UHFFFAOYSA-N (3-bromophenoxy)boronic acid Chemical compound OB(O)OC1=CC=CC(Br)=C1 ITZYPLMJTLJHGZ-UHFFFAOYSA-N 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- 125000006654 (C3-C12) heteroaryl group Chemical group 0.000 description 1
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 description 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
- 125000006736 (C6-C20) aryl 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
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-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
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 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
- ZPHQFGUXWQWWAA-UHFFFAOYSA-N 9-(2-phenylphenyl)carbazole Chemical group C1=CC=CC=C1C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 ZPHQFGUXWQWWAA-UHFFFAOYSA-N 0.000 description 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 description 1
- DGPBGQQNZHMXLR-UHFFFAOYSA-N CC(C)(C1CC=C2)c3ccccc3-c3c1c2c(-c(cc1)ccc1-c1cccc2c1[s]c1ccccc21)c1c3cccc1 Chemical compound CC(C)(C1CC=C2)c3ccccc3-c3c1c2c(-c(cc1)ccc1-c1cccc2c1[s]c1ccccc21)c1c3cccc1 DGPBGQQNZHMXLR-UHFFFAOYSA-N 0.000 description 1
- WGJABULXLYAQEU-UHFFFAOYSA-N CC(C)(c(cccc1)c1-c(cc1)c23)c2cccc3c1-c(cc1)ccc1-c1cccc(c2c3)c1[s]c2ccc3-c1cccc2c1CCCC2 Chemical compound CC(C)(c(cccc1)c1-c(cc1)c23)c2cccc3c1-c(cc1)ccc1-c1cccc(c2c3)c1[s]c2ccc3-c1cccc2c1CCCC2 WGJABULXLYAQEU-UHFFFAOYSA-N 0.000 description 1
- QXICENVPIUQNIK-UHFFFAOYSA-N CC(C)(c(cccc1)c1C(CC1)=C23)C2=CC=CC3=C1c1cccc(c2c3)c1[s]c2ccc3-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 Chemical compound CC(C)(c(cccc1)c1C(CC1)=C23)C2=CC=CC3=C1c1cccc(c2c3)c1[s]c2ccc3-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 QXICENVPIUQNIK-UHFFFAOYSA-N 0.000 description 1
- LMCUFIWDDJUCCY-UHFFFAOYSA-N CC(C)(c1c-2cccc1)c1cccc3c(C4C=CC(c5cccc(c6c7)c5[s]c6ccc7N(CCC5)c6c5cccc6)=CC4)ccc-2c13 Chemical compound CC(C)(c1c-2cccc1)c1cccc3c(C4C=CC(c5cccc(c6c7)c5[s]c6ccc7N(CCC5)c6c5cccc6)=CC4)ccc-2c13 LMCUFIWDDJUCCY-UHFFFAOYSA-N 0.000 description 1
- SBEWATSAGGNLOQ-UHFFFAOYSA-N CC(C)(c1c-2cccc1)c1cccc3c1c-2ccc3-c1cnc(-c(cc2)ccc2-c2cccc3c2[s]c2ccccc32)nc1 Chemical compound CC(C)(c1c-2cccc1)c1cccc3c1c-2ccc3-c1cnc(-c(cc2)ccc2-c2cccc3c2[s]c2ccccc32)nc1 SBEWATSAGGNLOQ-UHFFFAOYSA-N 0.000 description 1
- YROHQEALBUKSAR-UHFFFAOYSA-N CC1(C)c2ccccc2C2C=CC(c(c(C)c3)cc(C)c3-c3cccc4c3[s]c3ccc(C5CCCCC5)cc43)=C3C=CC=C1C23 Chemical compound CC1(C)c2ccccc2C2C=CC(c(c(C)c3)cc(C)c3-c3cccc4c3[s]c3ccc(C5CCCCC5)cc43)=C3C=CC=C1C23 YROHQEALBUKSAR-UHFFFAOYSA-N 0.000 description 1
- ZYKYEOPTJRUUMD-UHFFFAOYSA-N CC1(C2Sc3ccccc3C2C=CC1)c(cc1)ccc1-c1ccc-2c3c1cccc3C1(CCCC1)c1c-2cccc1 Chemical compound CC1(C2Sc3ccccc3C2C=CC1)c(cc1)ccc1-c1ccc-2c3c1cccc3C1(CCCC1)c1c-2cccc1 ZYKYEOPTJRUUMD-UHFFFAOYSA-N 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
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Abstract
化学式I的有机电致发光化合物:其中可变的R1至R18、Ar、X和m如说明书中所定义。这些化合物具有优秀的发光效率和优异的寿命性质。因此,它们可用于制造具有非常优越的工作寿命且由于改善了功率效率消耗更少功率的OLED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。
技术背景
在显示器件中,电致发光(EL)器件是优选的,因为它们作为自发射显示器件提供宽视角、优异的对比度和快速响应速率。伊斯曼柯达公司(EastmanKodak)在1987年首先开发了一种有机EL器件,该器件使用低分子量芳香族二胺和铝配合物作为形成电致发光层的物质[Appl.Phys.Lett.51,913,1987]。
在有机EL器件中,当电荷施加到形成在电子注入电极(阴极)和空穴注入电极(阳极)之间的有机层时,电子和空穴配对并产生激子。通过在激子失活的状态利用电致发光(磷光或荧光)来发光。有机EL器件以约10V的电压和约100~10,000cd/m2的高亮度来发射偏振光。有机EL器件的特征是通过对荧光材料进行简单选择,在蓝色到红色的光谱范围内发光。有机EL器件的优点在于,它可以在挠性透明基材(例如塑料)上形成,可在相比等离子体显示平板或无机EL显示器低的电压(10V或更低)下操作,消耗更少的功率以及提供优异的色彩。
在有机EL器件中,决定其性能(包括发光效率和工作寿命)最重要的因素是电致发光材料。电致发光材料的一些要求包括高固态电致发光量子产率、高电子和空穴迁移、真空沉积过程中的耐分解性、形成均匀薄膜的能力和稳定性。
有机电致发光材料一般分为高分子材料和低分子材料。从分子结构方面考虑,低分子材料包括金属配合物和不含金属的完全有机电致发光材料。这种电致发光材料包括螯合的配合物,如三(8-羟基喹啉)铝配合物,香豆素衍生物,四苯基丁二烯衍生物,二(苯乙烯基亚芳基)衍生物以及噁二唑衍生物。根据这些材料,据报道可得到从蓝色到红色的可见光范围的发光。
采用了三种电致发光材料(红色、绿色和蓝色)以实现全彩色有机发光二极管(OLED)显示器。重要的问题是发展具有高效率和长寿命的红色、绿色和蓝色电致发光材料,从而提升有机电致发光(EL)器件的整体特性。从功能方面考虑,EL材料分为基质材料和掺杂剂材料。通常已知,具有最优异EL性能的器件结构可用在基质中掺杂掺杂剂制备的EL层来制造。目前,开发具有高效率和长寿命的有机EL器件成为急迫的目标,考虑到中等到大尺寸OLED显示器面板所需的EL性能,特别急迫的是开发相比常规EL材料具有好很多EL性能的材料。从该观点来看,开发基质材料是需要解决的最重要的问题中的一个。基质材料(用作固态的溶剂和能量传输者)所需的性质是高纯度和合适的分子量,以能够进行真空气相沉积。另外,玻璃化转变温度和热分解温度应足够高,以确保热稳定性。另外,所述基质材料应具有高电化学稳定性,以提供长的寿命。易于形成无定形薄膜,它对于其他相邻材料具有高粘性,但是没有层间迁移。
当使用掺杂技术制造有机EL器件时,不能实现能量100%从基质分子转移到激发态的掺杂剂,基质材料和掺杂剂都会发光。特别地,在红色发光器件的情况下,因为基质材料发出可见性比掺杂剂高的波长范围的光,因此色纯度由于基质材料的暗淡发光而变差。如果实际运用了该技术,则要求增加发光寿命并改善耐久性。
目前,已知CBP是最广泛用作磷光材料的基质材料。已经报道了使用包含BCP、BAlq等的空穴阻挡层的高效OLED。先锋公司(日本)等已经报道了使用BAlq衍生物作为基质的高性能OLED。
BAlq衍生物
尽管这些材料提供了良好的电致发光特性,但是它们具有一些缺陷,如在真空高温沉积加工时会发生降解,这是因为它们具有低的玻璃化转变温度和差的热稳定性。因为OLED的功率效率是由(π/电压)×电流效率确定的,所以功率效率与电压成反比。需要高的功率效率来降低OLED的功率消耗。实际上,使用磷光材料的OLED提供比使用荧光材料的OLED好得多的电流效率(cd/A)。但是,当现有材料例如BAlq、CBP等用作磷光材料的基质时,相比使用荧光材料的OLED在功率效率(lm/W)方面没有明显优势,这是因为驱动电压较高。另外,OLED器件并不具有令人满意的工作寿命。因此,需要开发更稳定、更高性能的基质材料。
技术问题
因此,本发明的目的是提供一种发光效率和器件工作寿命相对现有材料得到改进且具有适当色坐标的优异骨架(backbone)的有机电致发光化合物,以解决上述问题。本发明的另一个目的是提供使用所述有机电致发光化合物作为电致发光材料的效率高且寿命长的有机电致发光器件。
技术方案
提供了一种如下化学式1表示的新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。因为本发明的有机电致发光化合物相比现有基质材料具有良好的发光效率和优异的寿命性质,所以它可用于制造具有非常优越的工作寿命且由于具有改善的功率效率消耗更少功率的OLED设备。
化学式1
其中
X表示-C(R20R21)、-N(R22)-、-S-、-O-或者-Si(R23R24)-;
Ar表示有或没有取代基的(C6-C30)亚芳基,或者有或没有取代基的(C3-C30)杂亚芳基;
R1至R16独立地表示氢、氘、卤素、有或没有取代基的(C1-C30)烷基、有或没有取代基的(C6-C30)芳基、有或没有取代基的(C3-C30)杂芳基、有或没有取代基的5-至7-元杂环烷基、与一个或多个有或没有取代基的(C3-C30)环烷基稠合的取代或未取代的(C6-C30)芳基、与一个或多个有或没有取代基的芳环稠合的5-至7-元杂环烷基、有或没有取代基的(C3-C30)环烷基、与一个或多个有或没有取代基的芳环稠合的(C3-C30)环烷基、有或没有取代基的(C6-C30)芳基(C1-C30)烷基、氰基、硝基、羟基、-NR31R32、-BR33R34、-PR35R36、-P(=O)R37R38、-SiR39R40R41或者-YR42、或者它们中的每一个可以通过有或没有稠环的取代或未取代的(C3-C30)亚烷基或者取代或未取代的(C3-C30)亚烯基与相邻取代基相连接以形成脂环或单环或多环芳环,其中所述脂环或单环或多环芳环的碳原子可以被一个或多个选自氮、氧和硫的杂原子取代;
R17、R18以及R20至R24独立地表示氢、氘、卤素、有或没有取代基的(C1-C30)烷基、有或没有取代基的(C6-C30)芳基、有或没有取代基的(C3-C30)杂芳基或者有或没有取代基的5-至7-元杂环烷基,或者它们中的每一个可以通过有或没有稠环的取代或未取代的(C3-C30)亚烷基或者取代或未取代的(C3-C30)亚烯基与相邻取代基相连接以形成脂环或单环或多环芳环,其中所述脂环或单环或多环芳环的碳原子可以被一个或多个选自氮、氧和硫的杂原子取代;
R31至R42独立地表示氢、氘、卤素、有或没有取代基的(C1-C30)烷基、有或没有取代基的(C6-C30)芳基、有或没有取代基的(C3-C30)杂芳基或者有或没有取代基的5-至7-元杂环烷基,或者它们中的每一个可以通过有或没有稠环的取代或未取代的(C3-C30)亚烷基或者取代或未取代的(C3-C30)亚烯基与相邻取代基相连接以形成脂环或单环或多环芳环,其中所述脂环或单环或多环芳环的碳原子可以被一个或多个选自氮、氧和硫的杂原子取代;
Y表示S或者O;
m表示0-3的整数,当m大于或等于2时,每一个Ar可以是相同或者不同的,并且可以与相邻取代基连接以形成环;以及
所述杂环烷基或杂芳基包含一个或多个选自B、N、O、S、P(=O)、Si和P的杂原子。
在本发明中,“烷基”、“烷氧基”以及其他包含“烷基”部分的取代基包括直链和支链类型。在本发明中,环烷基包含多环烃环,如有或没有取代基的金刚烷基或者有或没有取代基的(C7-C30)二环烷基以及单环烃环。
在本发明中,“芳基”表示通过从芳香烃除去一个氢原子得到的有机基团,可包括4元至7元、特别是5元至6元的单环或稠环,包括通过单键连接的多个芳基。
具体例子包括,但不限于,苯基、萘基、联苯基(biphenyl)、蒽基、茚基、芴基、菲基(phenanthryl)、苯并[9,10]菲基(triphenylenyl)、芘基、苝基(perylenyl)、屈基(chrysenyl)、并四苯基(naphthacenyl)、荧蒽基(fluoranthenyl)等。萘基包括1-萘基和2-萘基。蒽基包括1-蒽基、2-蒽基和9-蒽基,芴基包括1-芴基、2-芴基、3-芴基、4-芴基和9-芴基。在本发明中,“杂芳基”表示包含1至4个选自B、N、O、S、P(=O)、Si和P的杂原子作为芳环骨架原子、其他芳环骨架原子为碳的芳基基团。它可以是与苯环缩合得到的5元或6元单环杂芳基或多环杂芳基,且可部分饱和。所述杂芳基还包括之间具有单键的杂芳基基团。
杂芳基包括二价芳基基团,其中环中的杂原子可被氧化或季铵化,以形成例如N-氧化物或季铵盐。具体的例子包括单环杂芳基例如呋喃基、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、三唑基、四唑基、呋咱基(furazanyl)、吡啶基、吡嗪基、嘧啶基、哒嗪基等;多环杂芳基例如苯并呋喃基(benzofuranyl)、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)等;及其N-氧化物(例如吡啶基N-氧化物、喹啉基N-氧化物等);及其季铵盐等,但并不限于此。
本文所述的“(C1-C30)烷基”可包括(C1-C20)烷基或(C1-C10)烷基,且“(C6-C30)芳基”包括(C6-C20)芳基或(C6-C12)芳基。“(C3-C30)杂芳基”包括(C3-C20)杂芳基或(C3-C12)杂芳基,且“(C3-C30)环烷基”包括(C3-C20)环烷基或(C3-C7)环烷基。“(C2-C30)烯基或炔基”包括(C2-C20)烯基或炔基、(C2-C10)烯基或炔基。
在本文所述的术语“取代或未取代的取代基”或者“有或没有取代基”中,术语“取代的”表示未取代的取代基进一步被取代基取代。Ar、R1至R16、R17、R18、R20至R24、以及R31至R42的取代基可以被选自如下的一个或多个取代基进一步取代:氘、卤素、有或没有卤素取代基的(C1-C30)烷基、(C6-C30)芳基、有或没有(C6-C30)芳基取代基的(C3-C30)杂芳基、5元至7元杂环烷基、与一个或多个芳环稠合的5元至7元杂环烷基、(C3-C30)环烷基、与一个或多个芳环稠合的(C6-C30)环烷基、RaRbRcSi-、(C2-C30)烯基、(C2-C30)炔基、氰基、咔唑基、-NRdRe、-BRfRg、-PRhRi、-P(=O)RjRk、(C6-C30)芳基(C1-C30)烷基、(C1-C30)烷基(C6-C30)芳基、RlZ-、RmC(=O)-、RmC(=O)O-、羧基、硝基和羟基;其中Ra至Rl独立地表示(C1-C30)烷基、(C6-C30)芳基或者(C3-C30)杂芳基;Z表示S或者O;以及Rm表示(C1-C30)烷基、(C1-C30)烷氧基、(C6-C30)芳基或者(C6-C30)芳氧基。
X表示-C(R20R21)、-N(R22)-、-S-、-O-或者-Si(R23R24)-;
Ar表示有或没有取代基的(C6-C30)亚芳基,或者有或没有取代基的(C3-C30)杂亚芳基;
R1至R16独立地表示氢、氘、卤素、有或没有取代基的(C1-C30)烷基、有或没有取代基的(C6-C30)芳基、有或没有取代基的(C3-C30)杂芳基、与一个或多个有或没有取代基的(C3-C30)环烷基稠合的取代或未取代的(C6-C30)芳基、与一个或多个有或没有取代基的芳环稠合的5-至7-元杂环烷基、有或没有取代基的(C3-C30)环烷基、氰基、-NR31R32、-BR33R34或者-SiR39R40R41、或者它们中的每一个可以通过有或没有稠环的取代或未取代的(C3-C30)亚烷基或者取代或未取代的(C3-C30)亚烯基与相邻取代基相连接以形成脂环或单环或多环芳环;
R17、R18以及R20至R24独立地表示氢、氘、有或没有取代基的(C1-C30)烷基、有或没有取代基的(C6-C30)芳基或者有或没有取代基的(C3-C30)杂芳基,或者它们中每一个可通过有或没有稠环的取代或未取代的(C3-C30)亚烷基或者取代或未取代的(C3-C30)亚烯基连接到相邻取代基形成脂环或者单环或多环芳环;以及
R31至R34以及R39至R41独立地表示氢、氘、卤素、有或没有取代基的(C1-C30)烷基、有或没有取代基的(C6-C30)芳基或者有或没有取代基的(C3-C30)杂芳基。
更具体地R1至R7独立地表示氢、氟、叔丁基、环己基、二苯基氨基、N-咔唑基、二苯基甲基甲硅烷基、三苯甲硅烷基、苯并[9,10]菲基(triphenylenyl)、N-苯基-咔唑-3-基、二苯基三嗪基、二莱基硼烷基或者或者它们中的每一个可以通过有或没有稠环的取代或未取代的(C3-C30)亚烷基或者取代或未取代的(C3-C30)亚烯基与相邻取代基相连接以形成脂环或单环或多环芳环;
R8至R16独立地表示氢、甲基、苯基、氰基、嘧啶基或者三唑基,R8至R16的苯基、嘧啶基或者三唑基可以被选自甲基或苯基的一个或多个取代基进一步取代;
本发明的有机电致发光化合物的具体例子可以为下述化合物,但不限于此。
本发明的有机电致发光化合物可根据以下方案1所示进行制备。
方案1
其中
R1-R18、X、Ar和m的定义与化学式1相同。
提供了一种有机电致发光器件,它包含第一电极;第二电极;和插入所述第一电极和第二电极之间的一层或多层有机层,其中所述有机层包含化学式1表示的一种或多种有机电致发光化合物。有机层包含电致发光层,其中化学式1的有机电致发光化合物用作基质材料。
当化学式1的有机电致发光化合物用作基质时,包括了一种或多种掺杂剂。用于本发明的有机电致发光器件中的掺杂剂并没有特别限制,但可选自化学式2表示的化合物:
化学式2
M1L101L102L103
其中
M1是选自元素周期表第7族、第8族、第9族、第10族、第11族、第13族、第15族和第16族的金属,配体L101、L102、和L103独立地选自下述结构:
其中
R201至R203独立地表示氢、氘、有或没有卤素取代基的(C1-C30)烷基、有或没有(C1-C30)烷基取代基的(C6-C30)芳基或卤素;
R204至R219独立地表示氢、氘、有或没有取代基的(C1-C30)烷基、有或没有取代基的(C1-C30)烷氧基、有或没有取代基的(C3-C30)环烷基、有或没有取代基的(C2-C30)烯基、有或没有取代基的(C6-C30)芳基、有或没有取代基的单-或二-(C1-C30)烷基氨基、有或没有取代基的单-或二-(C6-C30)芳基氨基、SF5、有或没有取代基的三(C1-C30)烷基甲硅烷基、有或没有取代基的二(C1-C30)烷基(C6-C30)芳基甲硅烷基、有或没有取代基的三(C6-C30)芳基甲硅烷基、氰基或卤素;
R220至R223独立地表示氢、氘、有或没有卤素取代基的(C1-C30)烷基或者有或没有(C1-C30)烷基取代基的(C6-C30)芳基;
R224和R225独立地表示氢、氘、有或没有取代基的(C1-C30)烷基、有或没有取代基的(C6-C30)芳基或卤素,或者R224和R225可以通过有或没有稠环的(C3-C12)亚烷基或(C3-C12)亚烯基连接形成脂环或者单环或多环芳环;
R226表示有或没有取代基的(C1-C30)烷基、有或没有取代基的(C6-C30)芳基、有或没有取代基的(C5-C30)杂芳基或卤素;
R227至R229独立地表示氢、氘、有或没有取代基的(C1-C30)烷基、有或没有取代基的(C6-C30)芳基或卤素;以及
Q表示或者其中R231至R242独立地表示氢、氘、有或没有卤素取代基的(C1-C30)烷基、(C1-C30)烷氧基、卤素、有或没有取代基的(C6-C30)芳基、氰基、或者有或没有取代基的(C5-C30)环烷基,或者它们中的每一个可通过亚烷基或亚烯基连接到相邻取代基形成螺环或稠环,或者可通过亚烷基或亚烯基连接到R207或R208形成饱和或不饱和稠环。
化学式2的掺杂剂化合物可以用具有以下结构的化合物来表示,但是并不限于此:
在本发明的有机电子器件中,除了化学式1表示的有机电致发光化合物以外,所述有机层还可同时包括一种或多种选自芳胺化合物和苯乙烯基芳胺化合物的化合物。所述芳胺化合物或苯乙烯基芳胺化合物的例子参见韩国专利申请第10-2008-0123276、10-2008-0107606或10-2008-0118428号,但不限于此。
此外,在本发明的有机电致发光器件中,除了化学式1表示的有机电致发光化合物以外,所述有机层还可包括一种或多种选自元素周期表第1族、第2族的有机金属、第四周期和第五周期过渡金属、镧系金属和d-过渡元素的金属或络合化合物。所述有机层可包括电致发光层和电荷产生层。
另外,除了所述化学式1表示的有机电致发光化合物之外,所述有机层还可同时包括一种或多种发射蓝光、绿光或红光的有机电致发光层,以实现发射白光的有机电致发光器件。发蓝光、绿光或红光的化合物的例子可以是韩国专利申请第10-2008-0123276、10-2008-0107606或10-2008-0118428号所述的化合物,但不限于此。
在本发明的有机电致发光器件中,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”)可设置在电极对中的一个或两个电极的内表面上。更具体地说,硅或铝的金属硫属化物(包括氧化物)层可置于电致发光介质层的阳极表面上,且金属卤化物层或金属氧化物层可置于所述电致发光介质层的阴极表面上。从而得到工作稳定性。
例如,硫属化物可以是SiOx(1≤x≤2)、AlOx(1≤x≤1.5)、SiON、SiAlON等。例如,金属卤化物可以是LiF、MgF2、CaF2、稀土金属氟化物等。例如,金属氧化物可以是Cs2O、Li2O、MgO、SrO、BaO、CaO等。
在本发明的有机电致发光器件中,也优选在所制备的电极对的至少一个表面上设置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。在该情况下,由于电子传输化合物被还原成阴离子,从而促进电子从混合区注入以及传输到电致发光介质。另外,由于空穴传输化合物被氧化形成阳离子,从而促进空穴从混合区注入和传输到电致发光介质。优选的氧化性掺杂剂包括各种路易斯酸和受体化合物。优选的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。此外,具有两层或更多层电致发光层的发白光的电致发光器件可使用还原性掺杂剂层作为电荷产生层来制备。
有益的效果
因为本发明的有机电致发光化合物具有良好的发光效率和优异的寿命性质,它可用于制造具有非常优异的工作寿命的OLED器件。
本发明的实施方式
本发明进一步描述了本发明的有机电致发光化合物、制备该化合物的工艺以及使用该化合物的器件的发光性质。但是,这些实施例仅仅是为了阐述的目的,而不是为了限制本发明的范围。
[制备例1]制备化合物8
化合物1-1的制备
在7H-苯并[de]蒽-7-酮(40.0g,0.17mol)溶解于二乙醚(1000mL)之后,向其中缓慢加入AlCl3(28g,0.21mol)。将混合物搅拌15分钟之后,将混合物冷却到0℃并向其中缓慢加入氢化铝锂(LAH)(10g,0.26mol)。将混合物回流搅拌1小时之后,使得混合物在反应完成之后缓慢冷却到室温。向混合物中缓慢加入EA直到鼓泡终止。在加入6M HCl(100mL)之后,用蒸馏水和乙酸乙酯对混合物进行萃取。用MgSO4对有机层进行干燥并用旋转型蒸发器除去溶剂之后,使用二氯甲烷和己烷作为显影剂通过柱层析纯化得到化合物1-1(36.0g,95%)。
化合物1-2的制备
在化合物1-1(36.0g,0.16mol)溶解于DMSO(420mL)之后,在室温下加入叔丁醇纳(113.0g,1.2mol)并在70℃搅拌15分钟。向其中缓慢加入甲基碘(90mL,1.4mol)并搅拌1小时。在反应完成之后,将反应混合物在室温冷却,并向其中加入蒸馏水。在将混合物搅拌20分钟之后,制得固体并过滤。通过用甲醇和丙酮对固体进行重结晶得到化合物1-2(26g,63%)。
化合物1-3的制备
将化合物1-2(20g,90mmol)溶解于DMF(300mL)中,并向其中缓慢加入N-溴代琥珀酰亚胺(16g,90mmol)。将混合物在室温下搅拌1天。反应完成之后,用蒸馏水和EA萃取混合物。用MgSO4对有机层进行干燥并用旋转型蒸发器除去溶剂之后,使用二氯甲烷和己烷作为显影剂通过柱层析纯化得到化合物1-3(26g,91%)。
化合物1-4的制备
在将化合物1-3(26g,80.5mmol)、3-溴苯基硼酸(19.4g,96.6mmol)、Pd(PPh3)4(4.6g,4.03mmol)以及Na2CO3(12.8,120.8mmol)溶于400mL/100mL/80mL的甲苯/乙醇/蒸馏水之后,在100℃对混合物进行搅拌。反应完成之后,用蒸馏水和EA萃取反应混合物。用MgSO4对有机层进行干燥并用旋转型蒸发器除去溶剂之后,使用二氯甲烷和己烷作为显影剂通过柱层析纯化得到化合物1-4(24g,75%)。
化合物8的制备
在将化合物1-4(24g,60.1mmol)、二苯并[b,d]噻吩-4-基硼酸(16.4g,72.12mmol)、Pd(PPh3)4(3.4g,3.0mmol)以及Na2CO3(7.7g,72.12mmol)溶于300mL/60mL/50mL的甲苯/乙醇/蒸馏水之后,在100℃对混合物进行搅拌。反应完成之后,用蒸馏水和EA萃取反应混合物。用MgSO4对有机层进行干燥并用旋转型蒸发器除去溶剂之后,使用二氯甲烷和己烷作为显影剂通过柱层析纯化得到化合物8(26g,86%)。
[制备例2]制备化合物11
化合物2-1的制备
将化合物1-2(15g,0.06mol)溶于THF(300mL)之后,将混合物逐滴缓慢加入到Br2(7mL,0.13mol)中。将混合物在室温下搅拌12小时之后,用蒸馏水和EA对混合物进行萃取。用MgSO4对有机层进行干燥并用旋转型蒸发器除去溶剂之后,使用二氯甲烷和己烷作为显影剂通过柱层析纯化得到化合物2-1(13g,44%)。
化合物2-2的制备
在将化合物2-1(16g,44mmol)、二苯并[b,d]噻吩-4-基硼酸(5g,22mmol)、Pd(PPh3)4(1g,0.88mmol)以及Na2CO3(6.9g,66mmol)溶于100mL/50mL的甲苯/乙醇之后,在100℃对混合物搅拌12小时。反应完成之后,用蒸馏水和EA萃取混合物。用MgSO4对有机层进行干燥并用旋转型蒸发器除去溶剂之后,使用二氯甲烷和己烷作为显影剂通过柱层析纯化得到化合物2-2(5g,45%)。
化合物2-3的制备
在化合物2-2(5g,9.9mmol)溶于THF(100mL)之后,将混合物冷却到-78℃,将n-BuLi(4.4mL,己烷中2.5M,10.9mmol)缓慢加入其中。将混合物搅拌1小时之后,向混合物中缓慢加入三异丙基硼酸(2.7mL,12.9mmol)。在缓慢升高温度之后,将混合物在室温下搅拌1天。反应完成后,用2M HCl溶液淬灭反应混合物,并用EA/H2O萃取。用MgSO4去除水分并在减压下进行蒸馏之后,通过(MC/己烷)柱分离得到化合物2-3(3.2g,68%)。
化合物11的制备
在将化合物2-3(3.2g,6.8mmol)、2-氯-4,6-二苯基嘧啶(1.8g,5.7mmol)、Pd(PPh3)4(0.4g,0.29mmol)以及K2CO3(3.1g,17.1mmol)溶于40mL/20mL的甲苯/乙醇之后,在120℃对混合物搅拌12小时。反应完成之后,用EA/H2O萃取混合物。用MgSO4去除水分并在减压下进行蒸馏之后,通过(MC/己烷)柱分离得到化合物11(3g,65%)。
根据制备例1和2的方法制备有机电致发光化合物1至38。所制得的有机电致发光化合物的1H NMR和MS/FAB数据列在表1中。
表1
[实施例1]使用本发明的有机电致发光化合物制备OLED器件
使用本发明的电致发光材料制造了OLED器件。首先,将由玻璃制成的用于OLED的透明电极ITO薄膜(15Ω/□)(购自三星康宁公司(Samsung-Corning))依次用三氯乙烯、丙酮、乙醇和蒸馏水进行超声清洗,并在使用之前储存在异丙醇中。
然后,将ITO基片装在真空气相沉积设备的基片夹(folder)中,将4,4',4"-三(N,N-(2-萘基)-苯基氨基)三苯胺(2-TNATA)置于真空气相沉积设备的小室(cell)中,然后,排气,使室内真空度最高达到10-6托。接着,通过向所述小室施加电流以蒸发2-TNATA,在ITO基片上形成60nm厚的空穴注入层。
接着,向真空气相沉积设备的另一个小室中加入N,N'-二(α-萘基)-N,N'-二苯基-4,4'-二胺(NPB),向所述小室施加电流蒸发NPB,以在所述空穴注入层上形成20nm厚的空穴传输层。
形成空穴注入层和空穴传输层后,在其上面形成电致发光层,具体如下。将化合物8放置在真空气相沉积设备的小室中作为基质,将(piq)2Ir(acac)[二-(1-苯基异喹啉基)铱(III)乙酰丙酮酸盐]放置在另一室中作为掺杂剂。以不同的速率蒸发两种材料,这样以4至10重量%通过掺杂在空穴传输层上气相沉积30nm厚的电致发光层。
之后,在电致发光层上气相沉积20nm厚的三(8-羟基喹啉)-铝(III)(Alq)作为电子传输层。接着,气相沉积1至2nm厚的以下结构的喹啉合锂(Liq)作为电子注入层后,使用另一台真空气相沉积设备形成150nm厚的Al阴极,以制造OLED。
用于OLED的每种化合物通过在10-6托条件下真空升华进行纯化。
作为结果,确认6.2V的电压下电流流动为16.5mA/cm2,发射了1060cd/m2的红光。
[实施例2]使用本发明的有机电致发光化合物制备OLED器件
如实施例1所述制备OLED器件,不同之处在于在电致发光层上添加化合物12作为基质材料。
作为结果,确认6.3V的电压下电流流动为16.0mA/cm2,发射了1120cd/m2的红光。
[实施例3]使用本发明的有机电致发光化合物制备OLED器件
如实施例1所述制备OLED器件,不同之处在于在电致发光层上添加化合物37作为基质材料。
作为结果,确认6.5V的电压下电流流动为17.5mA/cm2,发射了1100cd/m2的红光。
[比较例1]
如实施例1所述的相同方式来制备OLED器件,不同之处在于,在真空气相沉积设备的一个小室中使用4,4'-二(咔唑-9-基)联苯(CBP)代替本发明的化合物作为基质材料,使用(piq)2Ir(acac)[二-(1-苯基异喹啉基)铱(III)乙酰丙酮酸盐]作为掺杂剂,使用二(2-甲基-8-喹啉合(quinolinato))(对-苯基-苯酚根合(phenolato))铝(III)(BAlq)作为空穴阻隔层。
作为结果,确认7.5V的电压下电流流动为15.3mA/cm2,发射了1000cd/m2的红光。
本发明的有机电致发光化合物相比于传统材料具有优良的特性。另外,使用本发明的有机电致发光化合物作为基质材料的器件具有优异的电致发光特性并降低了驱动电压,从而提高了功率效率并改善了功率消耗。
工业适用性
因为本发明的有机电致发光化合物具有良好的发光效率和优异的寿命性质,它可用于制造具有非常优异的工作寿命的OLED器件。
Claims (10)
1.一种由化学式1表示的有机电致发光化合物:
[化学式1]
其中
X表示-C(R20R21)、-N(R22)-、-S-、-O-或者-Si(R23R24)-;
Ar表示有或没有取代基的(C6-C30)亚芳基,或者有或没有取代基的(C3-C30)杂亚芳基;
R1至R16独立地表示氢、氘、卤素、有或没有取代基的(C1-C30)烷基、有或没有取代基的(C6-C30)芳基、有或没有取代基的(C3-C30)杂芳基、有或没有取代基的5-至7-元杂环烷基、与一个或多个有或没有取代基的(C3-C30)环烷基稠合的取代或未取代的(C6-C30)芳基、与一个或多个有或没有取代基的芳环稠合的5-至7-元杂环烷基、有或没有取代基的(C3-C30)环烷基、与一个或多个有或没有取代基的芳环稠合的(C3-C30)环烷基、有或没有取代基的(C6-C30)芳基(C1-C30)烷基、氰基、硝基、羟基、-NR31R32、-BR33R34、-PR35R36、-P(=O)R37R38、-SiR39R40R41或者-YR42、或者它们中的每一个可以通过有或没有稠环的取代或未取代的(C3-C30)亚烷基或者取代或未取代的(C3-C30)亚烯基与相邻取代基相连接以形成脂环或单环或多环芳环,其中所述脂环或单环或多环芳环的碳原子可以被一个或多个选自氮、氧和硫的杂原子取代;
R17、R18以及R20至R24独立地表示氢、氘、卤素、有或没有取代基的(C1-C30)烷基、有或没有取代基的(C6-C30)芳基、有或没有取代基的(C3-C30)杂芳基或者有或没有取代基的5-至7-元杂环烷基,或者它们中的每一个可以通过有或没有稠环的取代或未取代的(C3-C30)亚烷基或者取代或未取代的(C3-C30)亚烯基与相邻取代基相连接以形成脂环或单环或多环芳环,其中所述脂环或单环或多环芳环的碳原子可以被一个或多个选自氮、氧和硫的杂原子取代;
R31至R42独立地表示氢、氘、卤素、有或没有取代基的(C1-C30)烷基、有或没有取代基的(C6-C30)芳基、有或没有取代基的(C3-C30)杂芳基或者有或没有取代基的5-至7-元杂环烷基,或者它们中的每一个可以通过有或没有稠环的取代或未取代的(C3-C30)亚烷基或者取代或未取代的(C3-C30)亚烯基与相邻取代基相连接以形成脂环或单环或多环芳环,其中所述脂环或单环或多环芳环的碳原子可以被一个或多个选自氮、氧和硫的杂原子取代;
Y表示S或者O;
m表示0-3的整数,当m大于或等于2时,每一个Ar可以是相同或者不同的,并且可以与相邻取代基连接以形成环;以及
所述杂环烷基或杂芳基包含一个或多个选自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Ar、R1至R16、R17、R18、R20至R24、以及R31至R42的取代基可以被选自如下的一个或多个取代基进一步取代:氘、卤素、有或没有卤素取代基的(C1-C30)烷基、(C6-C30)芳基、有或没有(C6-C30)芳基取代基的(C3-C30)杂芳基、5元至7元杂环烷基、与一个或多个芳环稠合的5元至7元杂环烷基、(C3-C30)环烷基、与一个或多个芳环稠合的(C6-C30)环烷基、RaRbRcSi-、(C2-C30)烯基、(C2-C30)炔基、氰基、咔唑基、-NRdRe、-BRfRg、-PRhRi、-P(=O)RjRk、(C6-C30)芳基(C1-C30)烷基、(C1-C30)烷基(C6-C30)芳基、RlZ-、RmC(=O)-、RmC(=O)O-、羧基、硝基和羟基;其中Ra至Rl独立地表示(C1-C30)烷基、(C6-C30)芳基或者(C3-C30)杂芳基;Z表示S或者O;以及Rm表示(C1-C30)烷基、(C1-C30)烷氧基、(C6-C30)芳基或者(C6-C30)芳氧基。
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X表示-C(R20R21)、-N(R22)-、-S-、-O-或者-Si(R23R24)-;
Ar表示有或没有取代基的(C6-C30)亚芳基,或者有或没有取代基的(C3-C30)杂亚芳基;
R1至R16独立地表示氢、氘、卤素、有或没有取代基的(C1-C30)烷基、有或没有取代基的(C6-C30)芳基、有或没有取代基的(C3-C30)杂芳基、与一个或多个有或没有取代基的(C3-C30)环烷基稠合的取代或未取代的(C6-C30)芳基、与一个或多个有或没有取代基的芳环稠合的5-至7-元杂环烷基、有或没有取代基的(C3-C30)环烷基、氰基、-NR31R32、-BR33R34或者-SiR39R40R41、或者它们中的每一个可以通过有或没有稠环的取代或未取代的(C3-C30)亚烷基或者取代或未取代的(C3-C30)亚烯基与相邻取代基相连接以形成脂环或单环或多环芳环;
R17、R18以及R20至R24独立地表示氢、氘、有或没有取代基的(C1-C30)烷基、有或没有取代基的(C6-C30)芳基或者有或没有取代基的(C3-C30)杂芳基,或者它们中每一个可通过有或没有稠环的取代或未取代的(C3-C30)亚烷基或者取代或未取代的(C3-C30)亚烯基连接到相邻取代基形成脂环或者单环或多环芳环;以及
R31至R34以及R39至R41独立地表示氢、氘、卤素、有或没有取代基的(C1-C30)烷基、有或没有取代基的(C6-C30)芳基或者有或没有取代基的(C3-C30)杂芳基。
4.如权利要求3所述的有机电致发光化合物,其特征在于,所述R1至R7独立地表示氢、氟、叔丁基、环己基、二苯基氨基、N-咔唑基、二苯基甲基甲硅烷基、三苯甲硅烷基、苯并[9,10]菲基(triphenylenyl)、N-苯基-咔唑-3-基、二苯基三嗪基、二莱基硼烷基或者或者它们中的每一个可以通过有或没有稠环的取代或未取代的(C3-C30)亚烷基或者取代或未取代的(C3-C30)亚烯基与相邻取代基相连接以形成脂环或单环或多环芳环;
R8至R16独立地表示氢、甲基、苯基、氰基、嘧啶基或者三唑基,R8至R16的苯基、嘧啶基或者三唑基可以被选自甲基或苯基的一个或多个取代基进一步取代;
5.一种有机电致发光器件,所述器件包括如权利要求1至4中任一项所述的有机电致发光化合物。
6.如权利要求5所述的有机电致发光器件,其特征在于,该器件包含:第一电极;第二电极;以及插入所述第一电极和第二电极之间的一层或多层有机层,其中所述有机层包含一种或多种如权利要求1至4中任一项所述的有机电致发光化合物,和化学式2表示的一种或多种基质:
化学式2
M1L101L102L103
其中
M1是选自元素周期表第7族、第8族、第9族、第10族、第11族、第13族、第15族和第16族的金属,配体L101、L102、和L103独立地选自下述结构:
其中
R201至R203独立地表示氢、氘、有或没有卤素取代基的(C1-C30)烷基、有或没有(C1-C30)烷基取代基的(C6-C30)芳基或卤素;
R204至R219独立地表示氢、氘、有或没有取代基的(C1-C30)烷基、有或没有取代基的(C1-C30)烷氧基、有或没有取代基的(C3-C30)环烷基、有或没有取代基的(C2-C30)烯基、有或没有取代基的(C6-C30)芳基、有或没有取代基的单-或二-(C1-C30)烷基氨基、有或没有取代基的单-或二-(C6-C30)芳基氨基、SF5、有或没有取代基的三(C1-C30)烷基甲硅烷基、有或没有取代基的二(C1-C30)烷基(C6-C30)芳基甲硅烷基、有或没有取代基的三(C6-C30)芳基甲硅烷基、氰基或卤素;
R220至R223独立地表示氢、氘、有或没有卤素取代基的(C1-C30)烷基或者有或没有(C1-C30)烷基取代基的(C6-C30)芳基;
R224和R225独立地表示氢、氘、有或没有取代基的(C1-C30)烷基、有或没有取代基的(C6-C30)芳基或卤素,或者R224和R225可以通过有或没有稠环的(C3-C12)亚烷基或(C3-C12)亚烯基连接形成脂环或者单环或多环芳环;
R226表示有或没有取代基的(C1-C30)烷基、有或没有取代基的(C6-C30)芳基、有或没有取代基的(C5-C30)杂芳基或卤素;
R227至R229独立地表示氢、氘、有或没有取代基的(C1-C30)烷基、有或没有取代基的(C6-C30)芳基或卤素;以及
7.如权利要求6所述的有机电致发光器件,其特征在于,所述有机层还包含选自芳胺化合物和苯乙烯基芳胺化合物的一种或多种胺化合物。
8.如权利要求6所述的有机电致发光器件,其特征在于,所述有机层还包含选自元素周期表中第1族、第2族的有机金属、第四周期和第五周期过渡金属、镧系金属和d-过渡元素的一种或多种金属。
9.如权利要求6所述的有机电致发光器件,其特征在于,所述有机层包含电致发光层和电荷产生层。
10.如权利要求6所述的有机电致发光器件,其特征在于,所述有机电致发光器件是发射白光的有机电致发光器件,所述有机层还包含一层或多层发射蓝光、红光或绿光的有机电致发光层。
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