CN102036957A - 包含苯基吡啶单元的化合物 - Google Patents
包含苯基吡啶单元的化合物 Download PDFInfo
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- CN102036957A CN102036957A CN2009801199240A CN200980119924A CN102036957A CN 102036957 A CN102036957 A CN 102036957A CN 2009801199240 A CN2009801199240 A CN 2009801199240A CN 200980119924 A CN200980119924 A CN 200980119924A CN 102036957 A CN102036957 A CN 102036957A
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- 150000001875 compounds Chemical class 0.000 title claims description 29
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical group C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 title description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 37
- 230000005693 optoelectronics Effects 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 11
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 13
- 230000005540 biological transmission Effects 0.000 claims description 8
- 238000004040 coloring Methods 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 abstract description 18
- 239000002585 base Substances 0.000 description 72
- 239000010410 layer Substances 0.000 description 69
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 44
- 239000000460 chlorine Substances 0.000 description 44
- 239000000203 mixture Substances 0.000 description 44
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- -1 boric acid aryl ester Chemical class 0.000 description 39
- 239000007787 solid Substances 0.000 description 37
- 229910052757 nitrogen Inorganic materials 0.000 description 34
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 34
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- 238000003756 stirring Methods 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000010992 reflux Methods 0.000 description 24
- 238000005481 NMR spectroscopy Methods 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 238000001035 drying Methods 0.000 description 20
- 150000001335 aliphatic alkanes Chemical class 0.000 description 19
- 229910052760 oxygen Inorganic materials 0.000 description 19
- 239000001301 oxygen Substances 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 238000004440 column chromatography Methods 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 17
- 239000012153 distilled water Substances 0.000 description 15
- 238000002390 rotary evaporation Methods 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 235000019439 ethyl acetate Nutrition 0.000 description 14
- 239000000706 filtrate Substances 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 238000005406 washing Methods 0.000 description 13
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 125000002723 alicyclic group Chemical group 0.000 description 12
- 229940125846 compound 25 Drugs 0.000 description 12
- 238000000605 extraction Methods 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 11
- 239000012299 nitrogen atmosphere Substances 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- 229960001866 silicon dioxide Drugs 0.000 description 11
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 125000000524 functional group Chemical group 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 9
- 125000001931 aliphatic group Chemical group 0.000 description 9
- 239000004327 boric acid Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 9
- 229910052763 palladium Inorganic materials 0.000 description 9
- 229910004298 SiO 2 Inorganic materials 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 238000010790 dilution Methods 0.000 description 8
- 239000012895 dilution 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
- 239000000843 powder Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 150000001721 carbon Chemical group 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 238000007872 degassing Methods 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
- 235000015320 potassium carbonate Nutrition 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 230000006798 recombination Effects 0.000 description 7
- 238000005215 recombination Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- 239000006260 foam Substances 0.000 description 6
- 229910052741 iridium Inorganic materials 0.000 description 6
- 238000003760 magnetic stirring Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000010926 purge Methods 0.000 description 6
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 5
- 0 CC1Oc(c(C)ccc2)c2C1=CC=* Chemical compound CC1Oc(c(C)ccc2)c2C1=CC=* 0.000 description 5
- MDNVYGYNUVWYQM-UHFFFAOYSA-N OC(C)(C)C(C)(C)O.B(O)(O)B(O)O Chemical compound OC(C)(C)C(C)(C)O.B(O)(O)B(O)O MDNVYGYNUVWYQM-UHFFFAOYSA-N 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 229910052796 boron Inorganic materials 0.000 description 5
- 229940125851 compound 27 Drugs 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 229940093499 ethyl acetate Drugs 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 239000005864 Sulphur Substances 0.000 description 4
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 150000001502 aryl halides Chemical class 0.000 description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
- 239000002800 charge carrier Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 229940127204 compound 29 Drugs 0.000 description 4
- 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 4
- 125000001188 haloalkyl group Chemical group 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 229910052711 selenium Inorganic materials 0.000 description 4
- 239000011669 selenium Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 3
- UTAHFAJHGGPJEQ-UHFFFAOYSA-N (2-phenylphenyl)phosphane Chemical group PC1=CC=CC=C1C1=CC=CC=C1 UTAHFAJHGGPJEQ-UHFFFAOYSA-N 0.000 description 3
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- 229940126639 Compound 33 Drugs 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 3
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000000468 ketone group Chemical group 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 3
- XJYYTJSLGQZIJU-UHFFFAOYSA-N pyridin-3-yloxyboronic acid Chemical compound OB(O)OC1=CC=CN=C1 XJYYTJSLGQZIJU-UHFFFAOYSA-N 0.000 description 3
- 125000002769 thiazolinyl group Chemical group 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 2
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 2
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 2
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 2
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 2
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000004411 aluminium Substances 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
- 239000004305 biphenyl Substances 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 150000001642 boronic acid derivatives Chemical class 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229940126543 compound 14 Drugs 0.000 description 2
- 229940126142 compound 16 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 229940125877 compound 31 Drugs 0.000 description 2
- 229940127573 compound 38 Drugs 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
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- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
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- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 description 1
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- 239000007818 Grignard reagent Substances 0.000 description 1
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- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- SKOWZLGOFVSKLB-UHFFFAOYSA-N hypodiboric acid Chemical compound OB(O)B(O)O SKOWZLGOFVSKLB-UHFFFAOYSA-N 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 238000004519 manufacturing process Methods 0.000 description 1
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- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
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- 238000002156 mixing Methods 0.000 description 1
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- JGOAZQAXRONCCI-SDNWHVSQSA-N n-[(e)-benzylideneamino]aniline Chemical compound C=1C=CC=CC=1N\N=C\C1=CC=CC=C1 JGOAZQAXRONCCI-SDNWHVSQSA-N 0.000 description 1
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- 125000002347 octyl 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])[H] 0.000 description 1
- 235000019248 orcein Nutrition 0.000 description 1
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229940093916 potassium phosphate Drugs 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
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- 229910052706 scandium Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
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- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
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- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
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Abstract
Description
背景
本发明主要涉及有机化合物,具体地讲,涉及包含苯基吡啶单元的有机化合物和使用所述化合物的光电子器件。
光电子器件,例如有机发光器件(OLED),利用在受到偏压时发光的薄膜物质,这种光电子器件预期会成为平板显示器技术的越来越受欢迎的形式。这是因为OLED具有广泛的潜在应用,包括蜂窝式便携无线电话、个人数字助理(PDA)、计算机显示器、交通工具中的信息显示器、电视监视器和一般照明使用的光源。由于它们的亮色、宽视角、与全动感视频的相容性、宽温度范围、薄且一致的波形因数、低功率需求和低成本制造过程的可能性,可将OLED视为阴极射线管(CRT)和液晶显示器(LCD)的未来替代技术。由于它们的高发光效率,OLED可视为有潜力替代用于某些类型应用的白炽灯,甚至可能是荧光灯。
OLED具有夹层结构,该夹层结构由两个相对电极之间一个或多个有机层组成。例如,多层器件通常包括至少三层:空穴注入/传输层、发射层和电子传输层(ETL)。另外,也优选空穴注入/传输层用作电子阻挡层,ETL用作空穴阻挡层。单层OLED只在两个相对电极之间包括一个物质层。
简述
一方面,本发明涉及式I的有机化合物:
其中
R1在每次出现时独立为C1-C20脂族基团、C3-C20芳族基团或C3-C20脂环族基团;
R2在每次出现时独立为C1-C20脂族基团、C3-C20芳族基团或C3-C20脂环族基团;
a在每次出现时独立为0至4的整数;
b在每次出现时独立为0至3的整数;
Ar1为直接键或杂芳基、芳基或烷基或环烷基;
Ar2为杂芳基、芳基或烷基或环烷基;
c为0、1或2;且
n为2至4的整数。
另一方面,本发明涉及包含至少一种式I的有机化合物的光电子器件,特别是其中化合物存在于电子传输层的光电子器件。
详述
式I的有机化合物具有可用于光电子器件(例如有机发光器件(OLED))的性质,特别好的适用于其电子传输层。
一方面,本发明涉及式II的化合物
对于式I和II的化合物,Ar1独立选自
可用作Ar2的基团的实例包括
在具体实施方案中,Ar2独立选自
在更具体的实施方案中,Ar2独立选自
式I和II的有机化合物的实例包括:
在具体实施方案中,式I的有机化合物选自
可用Suzuki交叉偶联反应制备式I和II的化合物。用于Suzuki交叉偶联反应的一般方法包括在适合溶剂中,在碱和Pd催化剂存在下,混合芳基卤和硼酸芳基酯(或硼酸)。在惰性气氛下,将反应混合物加热一段时间。适合的溶剂包括但不限于二烷、THF、EtOH、甲苯及其混合物。示例性碱包括Na2CO3、K2CO3、Cs2CO3、磷酸钾及其水合物。碱可作为固体粉末或作为水溶液加到反应中。最常用的催化剂包括Pd(PPh3)4或Pd(OAc)2、Pd(dba)2,并加入第二配体。示例性配体包括二烷基膦基联苯配体,如以下所示结构III-VII,其中Cy为环己基。
一般有至少两种方法可用于使芳基卤转化成其相应的硼酸芳基酯。一种方法包括产生碳负离子,用BuLi实现锂-卤素交换,或者,用Mg产生格氏试剂,随后用硼酸酯使碳负离子猝灭,硼酸酯如硼酸三甲酯、硼酸三乙酯或硼酸三(异丙基)酯等。典型的方法包括在无水和惰性条件下,在无水溶剂中混合原料,无水溶剂如THF或乙醚。使反应冷却到-100℃或-80℃,滴加BuLi,并在此温度搅拌一定时间(1-5小时)。在此时间后,用适合的硼酸酯使中间碳负离子猝灭。使反应混合物温热至室温(RT),在RT下搅拌30分钟后,混合物用饱和NH4Cl溶液(0.5mL)处理,并浓缩至干,得到粗产物。
第二种方法利用Pd催化的硼基化反应。典型的方法包括在干燥和惰性气氛条件下,混合芳基卤和二硼酸频哪醇酯(pinacolate diborane)、无水碱和二烷基膦基联苯配体。保护烧瓶不受大气影响,并加入无水溶剂。在使溶液脱气15-30分钟后,向反应混合物加入Pd催化剂,并通过监测起始芳基卤的消失延时加热回流。随后,使反应混合物冷却到RT,并过滤。在浓缩后,得到粗反应产物。示例性无水碱包括NaHCO3、KHCO3和KOAc,特别是KOAc。示例性配体包括二烷基膦基联苯配体,如结构III-VII和反式-二氯双(三苯基膦)合钯(II)。
光电子器件,例如OLED,一般在最简单的情况下包括阳极层和相应的阴极层,并且有机电致发光层置于所述阳极和所述阴极之间。在跨电极施加偏压时,电子通过阴极注入电致发光层,同时电子从电致发光层从阳极去除(或者“空穴”“注入”其中)。在空穴与电子在电致发光层内组合形成单线态或三线态激子时发生发光,在单线态和/或三线态激子通过辐射衰减衰减到其基态时发生发光。
除了阳极、阴极和发光物质外,可在OLED中存在的其他组件包括空穴注入层、电子注入层和电子传输层。电子传输层不必与阴极直接接触,并且通常电子传输层也作为空穴阻挡层(locking layer),以防止空穴向阴极迁移。可在有机发光器件中存在的另外组件包括空穴传输层、空穴传输发射(发射)层和电子传输发射(发射)层。
在一个实施方案中,包含本发明的有机化合物的OLED可以为包含单线态发射器的荧光OLED。在另一个实施方案中,包含本发明的有机化合物的OLED可以为包含至少一个三线态发射器的磷光OLED。在另一个实施方案中,包含本发明的有机化合物的OLED包含至少一个单线态发射器和至少一个三线态发射器。包含本发明的有机化合物的OLED可包含一种或多种任何蓝色、黄色、橙色、红色磷光染料或其组合,包括过渡金属如Ir、Os和Pt的络合物。特别是,可使用电磷光(electrophosphorescent)和电荧光(electrofluorescent)金属络合物,如American Dye Source,Inc.,Quebec,Canada提供的那些。式I和II的有机化合物可以为OLED的发射层或空穴传输层或电子传输层或电子注入层或其任何组合的部分。
有机电致发光层,即发射层,为有机发光器件内的层,此层在工作时含显著浓度的电子和空穴两者,并且提供用于激子形成和发光的部位。空穴注入层为与阳极接触的层,此层促进空穴从阳极注入OLED的内层,电子注入层为与阴极接触的层,此层促进电子从阴极注入OLED,电子传输层则是促进电子从阴极和/或电子注入层传导到电荷重组部位的层。在含电子传输层的有机发光器件工作期间,在电子传输层中存在的大部分电荷载子(即空穴和电子)为电子,并且可通过发射层中存在的空穴和电子重组发生发光。空穴传输层是在OLED工作时促进空穴从阳极和/或空穴注入层传导到电荷重组部位,并且不必与阳极直接接触的层。空穴传输发射层是其中在OLED工作时促进空穴传导到电荷重组部位的层,其中大部分电荷载子为空穴,并且其中发射发生不仅通过与残余电子重组,而且通过从器件中别处的电荷重组区域转移能量。电子传输发射层是其中在OLED工作时促进电子传导到电荷重组部位的层,并且其中大部分电荷载子为电子,并且其中发射发生不仅通过与残余空穴重组,而且通过从器件中别处的电荷重组区域转移能量。
适合用作阳极的物质包括具有通过四点探针技术测定优选约1000欧姆/平方的体积电导率的物质。氧化锡铟(ITO)通常用作阳极,因为它对光透射基本上透明,并因此促进从电活性有机层发射的光造出。可用作阳极层的其他物质包括氧化锡、氧化铟、氧化锌、氧化锌铟、氧化锡铟锌、氧化锑及其混合物。
适合用作阴极的物质包括可将负电荷载子(电子)注入OLED的一个或多个内层的一般电导体,包括但不限于金属和金属氧化物,如ITO等。适合用作阴极20的各种金属包括K、Li、Na、Cs、Mg、Ca、Sr、Ba、Al、Ag、Au、In、Sn、Zn、Zr、Sc、Y、镧系元素、其合金及其混合物。用作阴极层的适合合金物质包括Ag-Mg、Al-Li、In-Mg、Al-Ca和Al-Au合金。分层的非合金结构也可用于阴极,如由较厚金属(如铝或银)层覆盖的金属(如钙)或金属氟化物(如LiF)的薄层。特别是,阴极可由单一金属(尤其是铝金属)组成。
在电子传输层中,可用式I和II的有机化合物代替传统物质,或除传统物质外可使用式I和II的有机化合物,传统物质为如聚(9,9-二辛基芴)、三(8-羟基喹啉根)合铝(Alq3)、2,9-二甲基-4,7-二苯基-1,1-菲咯啉、4,7-二苯基-1,10-菲咯啉、2-(4-联苯基)-5-(4-叔丁基苯基)-1,3,4-二唑、3-(4-联苯基)-4-苯基-5-(4-叔丁基苯基)-1,2,4-三唑、含1,3,4-二唑的聚合物、含1,3,4-三唑的聚合物、含喹喔啉的聚合物和氰基-PPV。
适用于空穴传输层的物质包括1,1-双((二-4-甲苯基氨基)苯基)环己烷、N,N′-双(4-甲基苯基)-N,N′-双(4-乙基苯基)-(1,1′-(3,3′-二甲基)联苯)-4,4′-二胺、四-(3-甲基苯基)-N,N,N′,N′-2,5-苯二胺、苯基-4-N,N-二苯基氨基苯乙烯、对-(二乙基氨基)苯甲醛二苯腙、三苯胺、1-苯基-3-(对-(二乙基氨基)苯乙烯基)-5-(对-(二乙基氨基)苯基)吡唑啉、1,2-反-双(9H-咔唑-9-基)环丁烷、N,N,N′,N′-四(4-甲基苯基)-(1,1′-联苯)-4,4′-二胺、铜酞菁、聚乙烯基咔唑、(苯基甲基)聚硅烷;聚(3,4-乙二氧基噻吩)(PEDOT)、聚苯胺、聚乙烯基咔唑、三芳基二胺、四苯基二胺、芳族叔胺、腙衍生物、咔唑衍生物、三唑衍生物、咪唑衍生物、具有氨基的二唑衍生物和美国专利号6,023,371公开的聚噻吩。
适用于发光层的物质包括电致发光聚合物,如聚芴,优选聚(9,9-二辛基芴)及其共聚物,如9,9′-二辛基芴-双-N,N′-(4-丁基苯基)二苯基胺共聚物(F8-TFB);聚(乙烯基咔唑)和聚对苯乙炔(polyphenylenevinylene)及其衍生物。另外,发光物质可包括磷光金属络合物,如红色染料三(1-苯基异喹啉)合铱(III)、绿色染料三(2-苯基吡啶)合铱和蓝色染料双(2-(4,6-二氟苯基)吡啶根(pyridinato)-N,C2)合铱(III)。除了前述物质外,也可使用式I和II的有机化合物。
式I和II的有机化合物可形成电子传输层或电子注入层或发光层的部分。因此,一方面,本发明涉及包含式I和II的有机化合物的更有效的光电子器件,例如OLED。OLED可以为含一种或多种任何蓝色、黄色、橙色、红色磷光染料或其组合的磷光器件。
定义
本文所用术语“芳族基团”是指具有至少一价的包含至少一个芳基的原子排列。具有至少一价的包含至少一个芳基的原子排列可包含杂原子,例如氮、硫、硒、硅和氧,或者可仅仅由碳和氢组成。本文所用术语“芳族基团”包括但不限于苯基、吡啶基、呋喃基、噻吩基、萘基、亚苯基和联苯基。如说明,芳族基团包含至少一个芳基。芳基总是为具有4n+2个“离域”电子的环状结构,其中“n”为等于1或更大的整数,例如苯基(n=1)、噻吩基(n=1)、呋喃基(n=1)、萘基(n=2)、甘菊环基(n=2)和蒽基(n=3)。芳族基团也可包含非芳族部分。例如,苄基为包含苯环(芳基)和亚甲基(非芳族部分)的芳族基团。类似地,四氢萘基为包括稠合到非芳族部分-(CH2)4-的芳基(C6H3)的芳族基团。为方便起见,本文所定义的术语“芳族基团”包含宽范围官能团,如烷基、烯基、炔基、卤代烷基、卤代芳基、共轭二烯基、醇基、醚基、醛基、酮基、羧酸基、酰基(例如羧酸衍生物,如酯和酰胺)、胺基、硝基等。例如,4-甲基苯基为包含甲基的C7芳族基团,所述甲基为烷基官能团。类似地,2-硝基苯基为包含硝基的C6芳族基团,硝基为官能团。芳族基团包括卤代芳族基团,如4-三氟甲基苯基、六氟异亚丙基双(4-苯-1-基氧基)(即,-OPhC(CF3)2PhO-)、4-氯甲基苯-1-基、3-三氟乙烯基-2-噻吩基、3-三氯甲基苯-1-基(即,3-CCl3Ph-)、4-(3-溴丙-1-基)苯-1-基(即,4-BrCH2CH2CH2Ph-)等。芳族基团的另外实例包括4-烯丙基氧基苯-1-氧基、4-氨基苯-1-基(即,4-H2NPh-)、3-氨基羰基苯-1-基(即,NH2COPh-)、4-苯甲酰基苯-1-基、二氰基亚甲基双(4-苯-1-基氧基)(即,-OPhC(CN)2PhO-)、3-甲基苯-1-基、亚甲基双(4-苯-1-基氧基)(即,-OPhCH2PhO-)、2-乙基苯-1-基、苯基乙烯基、3-甲酰基-2-噻吩基、2-己基-5-呋喃基、六亚甲基-1,6-双(4-苯-1-基氧基)(即,-OPh(CH2)6PhO-)、4-羟基甲基苯-1-基(即,4-HOCH2Ph-)、4-巯基甲基苯-1-基(即,4-HSCH2Ph-)、4-甲基硫基苯-1-基(即,4-CH3SPh-)、3-甲氧基苯-1-基、2-甲氧基羰基苯-1-基氧基(例如,甲基水杨酰基)、2-硝基甲基苯-1-基(即,2-NO2CH2Ph)、3-三甲基甲硅烷基苯-1-基、4-叔丁基二甲基甲硅烷基苯-1-基、4-乙烯基苯-1-基、亚乙烯基双(苯基)等。术语“C3-C10芳族基团”包括含至少3个但不多于10个碳原子的芳族基团。芳族基团1-咪唑基(C3H2N2-)表示C3芳族基团。苄基(C7H7-)表示C7芳族基团。
本文所用术语“脂环族基团”是指具有至少一价,并且包含环状但非芳族的原子排列的基团。本文所定义的“脂环族基团”不包含芳基。“脂环族基团”可包含一个或多个非环部分。例如,环己基甲基(C6H11CH2-)为脂环族基团,此脂环族基团包含环己基环(环状但非芳族的原子排列)和亚甲基(非环部分)。脂环族基团可包含杂原子,例如氮、硫、硒、硅和氧,或者可仅仅由碳和氢组成。为方便起见,本文所定义的术语“脂环族基团”包含宽范围官能团,如烷基、烯基、炔基、卤代烷基、共轭二烯基、醇基、醚基、醛基、酮基、羧酸基、酰基(例如羧酸衍生物,如酯和酰胺)、胺基、硝基等。例如,4-甲基环戊-1-基为包含甲基的C6脂环族基团,所述甲基为烷基官能团。类似地,2-硝基环丁-1-基为包含硝基的C4脂环族基团,硝基为官能团。脂环族基团可包含一个或多个可相同或不同的卤素原子。卤素原子包括例如氟、氯、溴和碘。包含一个或多个卤素原子的脂环族基团包括2-三氟甲基环己-1-基、4-溴二氟甲基环辛-1-基、2-氯二氟甲基环己-1-基、六氟异亚丙基-2,2-双(环己-4-基)(即,-C6H10C(CF3)2C6H10-)、2-氯甲基环己-1-基、3-二氟亚甲基环己-1-基、4-三氯甲基环己-1-基氧基、4-溴二氯甲基环己-1-基硫基、2-溴乙基环戊-1-基、2-溴丙基环己-1-基氧基(例如,CH3CHBrCH2C6H10O-)等。脂环族基团的另外实例包括4-烯丙基氧基环己-1-基、4-氨基环己-1-基(即,H2NC6H10-)、4-氨基羰基环戊-1-基(即,NH2COC5H8-)、4-乙酰基氧基环己-1-基、2,2-二氰基异亚丙基双(环己-4-基氧基)(即,-OC6H10C(CN)2C6H10O-)、3-甲基环己-1-基、亚甲基双(环己-4-基氧基)(即,-OC6H10CH2C6H10O-)、1-乙基环丁-1-基、环丙基乙烯基、3-甲酰基-2-四氢呋喃基、2-己基-5-四氢呋喃基、六亚甲基-1,6-双(环己-4-基氧基)(即,-O C6H10(CH2)6C6H10O-)、4-羟基甲基环己-1-基(即,4-HOCH2C6H10-)、4-巯基甲基环己-1-基(即,4-HSCH2C6H10-)、4-甲基硫基环己-1-基(即,4-CH3SC6H10-)、4-甲氧基环己-1-基、2-甲氧基羰基环己-1-基氧基(2-CH3OCOC6H10O-)、4-硝基甲基环己-1-基(即,NO2CH2C6H10-)、3-三甲基甲硅烷基环己-1-基、2-叔丁基二甲基甲硅烷基环戊-1-基、4-三甲氧基甲硅烷基乙基环己-1-基(例如,(CH3O)3SiCH2CH2C6H10-)、4-乙烯基环己烯-1-基、亚乙烯基双(环己基)等。术语“C3-C10脂环族基团”包括含至少3个但不多于10个碳原子的脂环族基团。脂环族基团2-四氢呋喃基(C4H7O-)表示C4脂环族基团。环己基甲基(C6H11CH2-)表示C7脂环族基团。
本文所用术语“脂族基团”是指具有至少一价的由直链或支链原子排列组成的非环状有机基团。脂族基团限定包含至少一个碳原子。包含脂族基团的原子排列可包含杂原子,例如氮、硫、硅、硒和氧,或者可仅仅由碳和氢组成。为方便起见,术语“脂族基团”在本文中限定包含宽范围官能团取代的有机基团作为“非环状直链或支链原子排列”的部分,所述官能团为如烷基、烯基、炔基、卤代烷基、共轭二烯基、醇基、醚基、醛基、酮基、羧酸基、酰基(例如羧酸衍生物,如酯和酰胺)、胺基、硝基等。例如,4-甲基戊-1-基为包含甲基的C6脂族基团,所述甲基为烷基官能团。类似地,4-硝基丁-1-基为包含硝基的C4脂族基团,硝基为官能团。脂族基团可以为含一个或多个卤素原子的卤代烷基,卤素原子可相同或不同。卤素原子包括例如氟、氯、溴和碘。包含一个或多个卤素原子的脂族基团包括烷基卤化物三氟甲基、溴二氟甲基、氯二氟甲基、六氟异亚丙基、氯甲基、二氟亚乙烯基、三氯甲基、溴二氯甲基、溴乙基、2-溴三亚甲基(例如,-CH2CHBrCH2-)等。脂族基团的另外实例包括烯丙基、氨基羰基(即,-CONH2)、羰基、2,2-二氰基异亚丙基(即,-CH2C(CN)2CH2-)、甲基(即,-CH3)、亚甲基(即,-CH2-)、乙基、亚乙基、甲酰基(即,-CHO)、己基、六亚甲基、羟基甲基(即,-CH2OH)、巯基甲基(即,-CH2SH)、甲基硫基(即,-SCH3)、甲基硫基甲基(即,-CH2SCH3)、甲氧基、甲氧基羰基(即,CH3OCO-)、硝基甲基(即,-CH2NO2)、硫代羰基、三甲基甲硅烷基(即,(CH3)3Si-)、叔丁基二甲基甲硅烷基、3-三甲氧基甲硅烷基丙基(即,(CH3O)3SiCH2CH2CH2-)、乙烯基、亚乙烯基等。作为进一步的实例,C1-C10脂族基团包含至少1个但不多于10个碳原子。甲基(即,CH3-)为C1脂族基团的实例。癸基(即,CH3(CH2)9-)为C10脂族基团的实例。
本文所用术语“杂芳基”是指其中一个或多个芳环的一个或多个碳原子由一个或多个杂原子置换的芳族或不饱和环,所述杂原子为如氮、氧、硼、硒、磷、硅或硫。杂芳基是指可以为单一芳环、多个芳环或偶合到一个或多个非芳环的一个或多个芳环的结构。在具有多个环的结构中,环可稠合在一起,共价连接,或连接到共同的基团,如醚、亚甲基或亚乙基部分。共同的连接基也可以为羰基,如苯基吡啶基酮中的羰基。如本文使用,环例如噻吩、吡啶、异唑、吡唑、吡咯、呋喃等或这些环的苯并稠合类似物由术语“杂芳基”限定。
本文所用术语“芳基”是指芳族取代基,该芳族取代基可以为单一芳环,或稠合在一起、共价连接或连接到共同的基团的多个芳环,所述共同的基团为如醚、亚甲基或亚乙基部分。其中一个或多个芳环可包括苯基、萘基、蒽基和联苯基。在具体实施方案中,芳基具有1至200个碳原子,1至50个碳原子,或1至20个碳原子。
本文所用术语“烷基”是指支链或非支链、饱和或不饱和的无环烃基。适合的烷基包括例如甲基、乙基、正丙基、异丙基、2-丙烯基(或烯丙基)、乙烯基、正丁基、叔丁基、异丁基(或2-甲基丙基)等。在具体实施方案中,烷基具有1至200个碳原子,1至50个碳原子,或1至20个碳原子。
本文所用术语“环烷基”是指具有单个环或多个稠合环的饱和或不饱和环状非芳族烃基。适合的环烷基包括例如环戊基、环己基、环辛烯基、二环辛基等。在具体实施方案中,环烷基具有3至200个碳原子,3至50个碳原子,或3至20个碳原子。
本文所述的任何数值包括以1单位增量从较低值到较高值的所有值,条件为在任何较低值和任何较高值之间隔离至少2个单位。作为实例,如果陈述组分的量或工艺变量(例如,温度、压力、时间等)的数值为例如1至90,优选20至80,更优选30至70,则在本说明书中旨在明确列举例如15至85、22至68、43至51、30至32等的数值。对于小于1的数值,则适当时将1单位认为是0.0001、0.001、0.01或0.1。这些只是具体打算的实例,在所列举的最低值和最高值之间的数值的所有可能组合均应认为是在本申请中以类似方式明确陈述。
实施例
实施例1-26描述本发明的化合物及制备它们使用的中间体的合成。除非另外规定,所有试剂均购自Aldrich Chemical Co.,Milwaukee,WI,USA和Acros Organics,无需进一步纯化即可使用。所有化合物通过1H-NMR表征,发现对应于所示结构。
实施例1:合成化合物25
向装配有磁力搅拌棒的100mL圆底Schlenk烧瓶加入1,3,5-三(3-溴苯)苯(6.52g,12.0mmol)、3-吡啶基硼酸(3.69g,30mmol)、25mL 2MNa2CO3水溶液和25mL 1,4-二烷。加入四(三苯基膦)合钯(0.54g,0.5mmol),混合物用五个真空/氮气反充循环脱气,然后在剧烈搅拌下加热到95℃,保持24小时。使反应混合物冷却到室温,并用CH2Cl2稀释。有机层用1N HCl、H2O和盐水洗涤,经Na2SO4干燥,并通过旋转蒸发浓缩至干。所得黄色固体通过柱层析在硅胶上纯化。洗脱液乙酸乙酯给出化合物25,为白色固体2.5g(39%)。1H NMR(400MHz,CDCl3)δ8.95(br s,2H),8.65(br s,2H),7.98-7.41(m,19H)。
实施例2:合成化合物1
将100mL两颈圆底烧瓶包以锡箔,并装配搅拌棒、配有氮气入口管的回流冷凝器和塞子。向烧瓶加入化合物25(0.864g,1.6mmol)、1,4-二烷(20mL)和四(三苯基膦)合钯(43.4mg,0.037mmol)。在反应过程中使装置保持在氮气气氛下。在室温搅拌混合物20分钟,然后通过漏斗加入溶于蒸馏水(4mL)的碳酸钾(0.42g,3mmol),随后加入1,2-双(4-(1,3,2-二氧杂硼杂环己烷(dioxaborinan)-2-基)苯氧基)(0.3g,0.79mmol)。搅拌反应混合物,并在油浴中加热回流20小时,然后冷却到环境温度。通过漏斗加入蒸馏水(20mL),所得混合物在布氏漏斗上过滤。将滤液转移到分液漏斗,并用CH2Cl2(3×30mL)萃取。合并的有机相经Na2SO4干燥,在滤纸上过滤,通过旋转蒸发浓缩至干(30℃,25mmHg)。所得黄色固体通过柱层析(SiO2;乙酸乙酯/THF(V/V:4/1)作为洗脱液)纯化,得到化合物1,为白色固体,将该固体溶于2mLCH2Cl2,在乙醚(50mL)中沉淀析出,得到最终产物化合物1(0.60,66%)。1H NMR(400MHz,CDCl3)δ8.96(s,4H),8.65(s,4H),7.98-7.91(m,16H),7.76-7.55(m,22H),7.43-7.40(m,4H),7.09(d,4H),4.43(s,4H)。
实施例3:合成化合物27
将100mL两颈圆底烧瓶包以锡箔,并装配搅拌棒、配有氮气入口管的回流冷凝器和塞子。向烧瓶加入化合物25(1.75g,3.24mmol)、1,4-二烷(30mL)和四(三苯基膦)合钯(86.9mg,0.073mmol)。在反应过程中使装置保持在氮气气氛下。在室温搅拌混合物20分钟,然后通过漏斗加入溶于蒸馏水(8mL)的碳酸钾(0.83g,5.9mmol),随后加入2-氟吡啶-5-硼酸频哪醇酯(1.1g,4.8mmol)。搅拌反应混合物,并在油浴中加热回流20小时,然后冷却到环境温度。通过漏斗加入蒸馏水(30mL),所得混合物在布氏漏斗上过滤。将滤液转移到分液漏斗,并用CH2Cl2(3×30mL)萃取。合并的有机相经Na2SO4干燥,在滤纸上过滤,通过旋转蒸发浓缩至干(30℃,25mmHg)。所得黄色固体通过柱层析纯化,得到白色固体1.67g(93%)。1HNMR(400MHz,CDCl3)δ8.95(d,2H),8.65(m,2H),8.52(d,1H),8.07(m,1H),7.98-7.79(m,11H),7.65-7.59(m,6H),7.42(t,2H),7.06(t,1H)。
实施例4:合成化合物2
向装配有磁力搅拌棒和Stark-Dean分水器及回流冷凝器的25mLSchlenk烧瓶加入甲苯(5mL)和DMF(5mL),并置于氮气气氛下。将化合物27(0.91g,1.64mmol)、六氟异丙叉基双(4-羟基苯)(0.242g,0.72mmol)和碳酸铯(0.61g,1.9mmol)的混合物溶于溶剂。在剧烈搅拌下,将混合物加热到140℃,保持24小时。使反应混合物冷却到室温,并用CH2Cl2稀释。有机层用1N HCl、H2O和盐水洗涤,经Na2SO4干燥,并通过旋转蒸发浓缩至干。所得黄色固体通过柱层析在硅胶上纯化。洗脱液乙酸乙酯/THF(V/V:4/1)给出化合物2,为白色固体0.99g(97%)。然后,将白色固体重新溶于乙醇,加入少量CH2Cl2,以帮助溶解。在过夜后析出一些粉末,收集白色粉末(620mg)。1H NMR(400MHz,CDCl3)δ8.95(d,4H),8.64(m,4H),8.55(d,2H),8.05-7.88(m,18H),7.78-7.75(m,6H),7.64-7.61(m,12H),7.50(m,4H),7.42(m,4H),7.23(d,4H),7.09(d,4H)。
实施例5:合成化合物28
向二烷(50mL)中化合物25(1.6g,3mmol)、Pd(PPh3)4(0.18g,0.16mmol)和三-叔丁基膦(6mL,10%重量,溶于己烷)的混合物依次加入3-羟基苯基硼酸(0.62g,4.53mmol)、Na2CO3(0.62g)、MeOH(16mL)和H2O(8mL)。此混合物用五个真空/氮气反充循环脱气,然后在回流下加热24小时。在冷却至室温后,使混合物在H2O(100mL)和CH2Cl2(100mL)之间分配。收集有机层,经MgSO4干燥,浓缩得到粗产物,该粗产物通过柱层析(SiO2;乙酸乙酯为洗脱液)纯化,得到化合物28,为白色固体(1.60,96%)。1H NMR(400MHz,CDCl3):δ=8.97(s,2H),8.65(s,2H),7.99(d,2H),7.90(m,6H),7.77(m,2H),7.70(d,2H),7.63(m,5H),7.55(t,1H),7.43(t,2H),7.34(t,1H),7.21(m,2H),6.91(d,1H)。
实施例6:合成化合物3
向装配有磁力搅拌棒和Stark-Dean分水器及回流冷凝器的25mLSchlenk烧瓶加入甲苯(5mL)和DMF(5mL),并置于氮气气氛下。将化合物27(0.37g,0.67mmol)、化合物28(0.37g,0.66mmol)和碳酸铯(0.284g,0.87mmol)的混合物溶于溶剂。在剧烈搅拌下,将混合物加热到140℃,保持24小时。使反应混合物冷却到室温,并用CH2Cl2稀释。有机层用1N HCl、H2O和盐水洗涤,经Na2SO4干燥,并通过旋转蒸发浓缩至干。所得黄色固体通过柱层析在硅胶上纯化。洗脱液乙酸乙酯/THF(V/V:4/1)给出化合物3,为白色固体0.623g(87%)。然后,将白色固体重新溶于乙醇,加入少量CH2Cl2,以帮助溶解。在过夜后析出一些粉末,收集白色粉末(320mg)。1H NMR(400MHz,CDCl3)δ8.94(d,4H),8.64(m,4H),8.52(d,1H),8.01-7.40(m,38H),7.22(m,1H),7.08(d,1H)。
实施例8:合成化合物4
向二烷(50mL)中酯29(3g,5mmol)的混合物依次加入3,5-二溴吡啶(0.39g,1.67mmol)、Cs2CO3(6.5g,20mmol)、Pd(OAc)2(35mg)和PCyBiPhen(150mg)。此混合物用五个真空/氮气反充循环脱气,然后加热到90度,保持16小时。在冷却至室温后,将混合物过滤,并用CH2Cl2(20mL)洗涤。收集滤液,浓缩得到粗产物,该粗产物通过柱层析纯化,得到化合物4(1.55g,93%)。1H NMR(400MHz,CDCl3)δ8.95(m,6H),8.64(m,4H),8.20(m,1H),7.98-7.90(m,16H),7.79-7.62(m,19H),7.41(m,4H)。将产物溶于3mL CH2Cl2,然后缓慢加入乙醚(50mL)。沉淀析出白色粉末,通过离心收集,然后用乙醚洗涤粉末3次。
实施例9:合成化合物4
用氮气吹扫含Na2CO3(1.10g)的甲苯(10mL)/H2O(5.0mL)/EtOH(5.0mL)的双相混合物。向此溶液加入硼酸化合物36(0.500g,1.00mmol),3,5-二溴吡啶(107mg,0.450mmol),随后加入Pd(PPh3)4(40.0mg,0.0400mmol)。将反应放在惰性氮气气氛下,并温和加热回流16小时。使混合物冷却到室温,与EtOAc(50mL)一起转移到分液漏斗,并用盐水(2×100mL)洗涤。有机层经Na2SO4干燥,与3-巯基丙基官能化的硅胶(1.0g,Aldrich)一起搅拌,并过滤。滤饼用5%MeOH/CH2Cl2洗涤,将滤液浓缩至干,得到泡沫状物。粗物质通过SiO2层析,用5%MeOH/CH2Cl2洗脱,得到产物,为白色泡沫状物。收率290mg,65%。1H NMR(400MHz,CD2Cl2,25℃)δ7.39(m,4H),7.64(m,10H),7.76(m,8H),7.98(m,14H),8.04(t,2H),8.25(t,1H),8.58(m,4H),8.93(m,6H)。
实施例10:合成化合物5
向2,8-二溴二苯并呋喃(1g,3.07mmol)的20mL DMSO溶液加入二硼酸二(频哪醇酯)(bispinacolatiodiboron)(1.74g,6.75mmol)、KOAc(2g,21mmol)和PdCl2(PPh3)2(149mg,0.21mmol),并在80℃搅拌溶液24小时。在反应混合物冷却到室温后,过滤除去催化剂,并用CH2Cl2洗涤。然后用去离子H2O(50mL)洗涤滤液5次,有机层经Mg2SO4干燥,过滤,浓缩,通过柱层析在硅胶上纯化(己烷/EtOAc=10∶1),得到2,8-二(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)二苯并呋喃(0.4g,31%)。1H NMR(400MHz,CDCl3)δ8.51(s,2H),7.92(d,2H),7.57(d,2H),1.40(s,24H)。
将50mL两颈圆底烧瓶包以锡箔,并装配搅拌棒、配有氮气入口管的回流冷凝器和塞子。向烧瓶加入2,8-二(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)二苯并呋喃(0.38g,0.92mmol)、化合物27(1.1g,2.02mmol)、1,4-二烷(20mL)和四(三苯基膦)合钯(86.9mg,0.073mmol)。在反应过程中使装置保持在氮气气氛下。在室温搅拌混合物20分钟,然后通过漏斗加入溶于蒸馏水(8mL)的碳酸钾(0.83g,5.9mmol)。搅拌反应混合物,并在油浴中加热回流20小时,然后冷却到环境温度。通过漏斗加入蒸馏水(20mL),所得混合物在布氏漏斗上过滤。将滤液转移到分液漏斗,并用CH2Cl2(3×30mL)萃取。合并的有机相经Na2SO4干燥,在纸上过滤,通过旋转蒸发浓缩至干(30℃,25mmHg)。然后通过柱层析在硅胶上纯化(EtOAc/THF=10∶1),得到化合物5(0.596g,60%)。1H NMR(400MHz,CDCl3)δ8.93(m,4H),8.62(m,4H),8.29(m,2H),8.0-7.91(m,15H),7.81-7.61(m,22H),7.39(m,4H)。
实施例11:合成化合物29
将50mL两颈圆底烧瓶包以锡箔,并装配搅拌棒、配有氮气入口管的回流冷凝器和塞子。向烧瓶加入化合物25(2.175g,4.03mmol)、THF(20mL)、1,4-二烷(5mL)、二硼酸频哪醇酯(3.1g,12.2mmol)、Pd(OAc)2(23.0mg,0.100mmol)干燥KOAc(1.47g,15.0mmol)和PcyBiPhen(配体IV,103mg,0.250mmol)。在反应过程中使装置保持在氮气气氛下。搅拌反应混合物,并在油浴中加热回流15小时,然后冷却到环境温度。通过漏斗加入蒸馏水(30mL),所得混合物在布氏漏斗上过滤。将滤液转移到分液漏斗,并用CH2Cl2(3×30mL)萃取。合并的有机相经Na2SO4干燥,在滤纸上过滤,通过旋转蒸发浓缩至干(30℃,25mmHg)。所得固体通过柱层析纯化,得到白色固体2.296g(97%)。1H NMR(400MHz,CDCl3)δ8.95(d,2H),8.64(m,2H),8.15(d,1H),7.98(m,2H),7.90-7.77(m,9H),7.64(m,4H),7.53(t,1H),7.42(m,2H),1.38(s,12H)。
实施例12:合成化合物29和35
向装配有冷凝器、氮气入口管和橡胶隔膜的火焰干燥3颈圆底烧瓶加入化合物25(2.70g,5.00mmol)、二硼酸频哪醇酯(3.81g,15.0mmol)、干燥KOAc(1.47g,15.0mmol)和环己基膦配体(103mg,0.250mmol)。然后保护烧瓶不受大气影响,加入无水THF(20mL),二烷(5mL),由N2吹扫通过搅拌的溶液使溶液脱气。在15分钟后,向反应混合物加入Pd(OAc)2(23.0mg,0.100mmol),将混合物加热回流12小时。在此时间过去后,使反应混合物冷却到室温(RT),并通过硅藻土过滤。滤饼用EtOAc洗涤,将滤液浓缩至干。残余物用EtOAc洗脱液通过SiO2层析。收率2.65g,90%。1H NMR(400MHz,CD2Cl2,25℃)δ1.39(s,12H),7.41(m,2H),7.52(t,1H),7.63(m,4H),7.82(m,4H),7.92(s,3H);7.96(m,2H),8.00(m,2H),8.13(s,1H),8.60(m,2H),8.94(d,2H)。通过加热稀H2SO4和MeOH混合物中的酯,使硼酸频哪醇酯转化成相应的硼酸。在酸用NaHCO3中和后,使浓缩至干后得到的固体悬浮于H2O中,过滤,用H2O洗涤,并干燥。
实施例13:合成化合物30
将100mL两颈圆底烧瓶包以锡箔,并装配搅拌棒、配有氮气入口管的回流冷凝器和塞子。向烧瓶加入化合物29(2.296g,3.914mmol)、3,5-二溴吡啶(1.391g,5.87mmol)、1,4-二烷(30mL)和四(三苯基膦)合钯(86.9mg,0.073mmol)。在反应过程中使装置保持在氮气气氛下。在室温搅拌混合物20分钟,然后通过漏斗加入溶于蒸馏水(8mL)的碳酸钾(0.83g,5.9mmol)。搅拌反应混合物,并在油浴中加热回流20小时,然后冷却到环境温度。通过漏斗加入蒸馏水(30mL),所得混合物在布氏漏斗上过滤。将滤液转移到分液漏斗,并用CH2Cl2(3×30mL)萃取。合并的有机相经Na2SO4干燥,在滤纸上过滤,通过旋转蒸发浓缩至干(30℃,25mmHg)。所得黄色固体通过柱层析纯化,得到白色固体1.45g(60%)。1H NMR(400MHz,CDCl3)δ8.95(d,2H),8.85(d,1H),8.52(d,1H),8.71(d,1H),8.65(m,2H),8.12(m,1H),7.98(m,2H),7.91-7.87(m,6H),7.82-7.77(m,3H),7.65(m,6H),7.42(t,2H)。
实施例14:合成化合物31
向装配有磁力搅拌棒的100mL圆底Schlenk烧瓶加入1-溴-3-碘苯(5.754g,20.3mmol)、3-吡啶基硼酸(2.5g,20.3mmol)、25mL 2MNa2CO3水溶液和25mL 1,4-二烷。加入四(三苯基膦)合钯(0.54g,0.5mmol),混合物用五个真空/氮气反充循环脱气,然后在剧烈搅拌下加热到95℃,保持24小时。使反应混合物冷却到室温,并用CH2Cl2稀释。有机层用1N HCl、H2O和盐水洗涤,经Na2SO4干燥,并通过旋转蒸发浓缩至干。所得黄色固体通过柱层析在硅胶上纯化。洗脱液乙酸乙酯/己烷(3/97)给出化合物31,为浅黄色油状物3.6g(77%)。1HNMR(400MHz,CDCl3)δ8.82(br s,1H),8.63(m,1H),7.85(m,1H),7.73(m,1H),7.53(m,2H),7.36(m,2H)。
实施例15:合成化合物32
将50mL两颈圆底烧瓶包以锡箔,并装配搅拌棒、配有氮气入口管的回流冷凝器和塞子。向烧瓶加入3-(3-溴苯基)吡啶(2g,8.54mmol)、THF(20mL)、1,4-二烷(5mL)、二硼酸频哪醇酯(4.34g,17.09mmol)、干燥KOAc(1.01g,10.4mmol)、Pd(OAc)2(17mg,0.07mmol)和PCyBiPhen(配体IV,71mg,0.172mmol)。在反应过程中使装置保持在氮气气氛下。搅拌反应混合物,并在油浴中加热回流15小时,然后冷却到环境温度。通过漏斗加入蒸馏水(30mL),所得混合物在布氏漏斗上过滤。将滤液转移到分液漏斗,并用CH2Cl2(3×30mL)萃取。合并的有机相经Na2SO4干燥,在滤纸上过滤,通过旋转蒸发浓缩至干(30℃,25mmHg)。所得固体通过柱层析纯化,得到白色固体2.15g(90%)。1H NMR(400MHz,CDCl3)δ8.89(br s,1H),8.60(d,1H),8.05(s,1H),7.92(m,1H),7.87(m,1H),7.7(m,1H),7.51(m,1H),7.37(m,1H),1.39(s,12H)。
实施例16:合成化合物33
向装配有磁力搅拌棒的100mL圆底Schlenk烧瓶加入化合物32(2.15g,7.65mmol)、1,3,5-三溴苯(3.61g,11.5mmol)、25mL 2MNa2CO3水溶液和25mL 1,4-二烷。加入四(三苯基膦)合钯(0.54g,0.5mmol),混合物用五个真空/氮气反充循环脱气,然后在剧烈搅拌下加热到95℃,保持24小时。使反应混合物冷却到室温,并用CH2Cl2稀释。有机层用1N HCl、H2O和盐水洗涤,经Na2SO4干燥,并通过旋转蒸发浓缩至干。所得黄色固体通过柱层析在硅胶上纯化。洗脱液乙酸乙酯/己烷(3/97)给出化合物33,为白色固体1.84g(62%)。1H NMR(400MHz,CDCl3)δ8.91(br s,1H),8.66(m,1H),7.94(m,1H),7.72-7.69(m,4H),7.63-7.58(m,3H),7.42(m,1H)。
实施例17:合成化合物34
将50mL两颈圆底烧瓶包以锡箔,并装配搅拌棒、配有氮气入口管的回流冷凝器和塞子。向烧瓶加入化合物33(1.84g,4.72mmol)、THF(20mL)、1,4-二烷(5mL)、二硼酸频哪醇酯(6.0g,23.63mmol)、干燥KOAc(2.3g,23.92mmol)、Pd(OAc)2(36mg,0.15mmol)和PCyBiPhen(162mg,0.39mmol)。在反应过程中使装置保持在氮气气氛下。搅拌反应混合物,并在油浴中加热回流15小时,然后冷却到环境温度。通过漏斗加入蒸馏水(30mL),所得混合物在布氏漏斗上过滤。将滤液转移到分液漏斗,并用CH2Cl2(3×30mL)萃取。合并的有机相经Na2SO4干燥,在滤纸上过滤,通过旋转蒸发浓缩至干(30℃,25mmHg)。所得固体通过柱层析纯化,得到白色固体1.12g(49%)。1H NMR(400MHz,CDCl3)δ8.93(m,1H),8.64(m,1H),8.32(m,1H),8.19(d,2H),7.98(m,1H),7.86(m,1H),7.73(m,1H),7.56(m,2H),7.42(m,1H),1.38(s,24H)。
实施例18:合成化合物6
将100mL两颈圆底烧瓶包以锡箔,并装配搅拌棒、配有氮气入口管的回流冷凝器和塞子。向烧瓶加入化合物30(0.96g,1.56mmol)、化合物34(0.335g,0.7mmol)、1,4-二烷(30mL)和四(三苯基膦)合钯(86.9mg,0.073mmol)。在反应过程中使装置保持在氮气气氛下。在室温搅拌混合物20分钟,然后通过漏斗加入溶于蒸馏水(8mL)的碳酸钾(0.83g,5.9mmol)。搅拌反应混合物,并在油浴中加热回流20小时,然后冷却到环境温度。通过漏斗加入蒸馏水(30mL),所得混合物在布氏漏斗上过滤。将滤液转移到分液漏斗,并用CH2Cl2(3×30mL)萃取。合并的有机相经Na2SO4干燥,在滤纸上过滤,通过旋转蒸发浓缩至干(30℃,25mmHg)。所得黄色固体通过柱层析纯化,得到白色固体0.63g(66%)。1H NMR(400MHz,CDCl3)δ8.95(m,9H),8.63(m,5H),8.22(m,2H),7.97-7.89(m,21H),7.80-7.61(m,21H),7.39(m,5H)。
实施例19:合成化合物36
向装配有氮气入口管和橡胶隔膜的火焰干燥3颈圆底烧瓶加入化合物25(2.0g,3.7mmol)。将烧瓶置于惰性气氛下,并加入无水THF(50mL)。使反应冷却到-100℃,滴加1.6M BuLi(2.6mL,4.1mmol),并搅拌10分钟。在-80℃向反应加入硼酸三乙酯,并在此温度搅拌1小时。使反应混合物温热至RT,在RT搅拌30分钟后,混合物用饱和NH4Cl(0.5mL)溶液处理,并浓缩至干。残余物用H2O(3×100mL)洗涤,在RT在MeOH(50mL)和5%HCl(5mL)的混合物中搅拌过夜。溶液用NaHCO3中和,除去溶剂至干。使残余物悬浮于丙酮(200mL)中,过滤收集沉淀物(0.46g)。将母液浓缩至干,残余物用EtOAc超声处理,过滤收集白色固体,并用EtOAc洗涤。收率0.65g,35%。1HNMR(400MHz,[D6]-DMSO,25℃)δ7.51(m,3H),7.64(m,2H),7.80(m,3H),7.96(m,3H),8.05(s,2H),8.12(s,1H),8.21(m,5H),8.30(s,1H),8.60(m,2H),9.05(s,2H)。
实施例20:合成化合物25和35
向装配有冷凝器、塞子和氮气入口管的3颈圆底烧瓶中的H2O(50mL)和二烷(50mL)的吹扫混合物加入Na2CO3(10.6g,100mmol)、1,3,5-(3-溴苯基)-苯(10.9g,20.0mmol)、3-吡啶基硼酸(5.41g,44.0mmol)。在用N2吹扫15分钟后,加入Pd(PPh3)4(0.924g,0.800mmol),并将混合物温和加热回流24小时。使反应混合物冷却到室温(RT),用CH2Cl2(100mL)稀释,转移到含饱和NaHCO3的分液漏斗,反应烧瓶用CH2Cl2和H2O清洗。除去有机层,水层用CH2Cl2(100mL)萃取,经Na2SO4干燥,并浓缩至干,得到泡沫状物。粗产物通过SiO2层析纯化,用EtOAc洗脱。在SiO2上分离后收集两种产物。收率:化合物25(4.55g,42%)和35(2.41g,22%)。1H NMR化合物25(400MHz,CD2Cl2,25℃)δ7.40(m,3H),7.55(m,1H),7.65(m,5H),7.78(m,2H),7.88(d,2H),7.94(m,4H),7.98(m,2H),8.60(dd,2H),8.93(d,2H);1HNMR化合物35(400MHz,CD2Cl2,25℃)δ7.40(m,3H),7.55(m,2H),7.65(m,4H),7.77(m,2H),7.89(m,5H),7.99(m,1H),8.61(dd,1H),8.93(d,1H)。
实施例21:合成化合物7
用氮气吹扫含Na2CO3(579mg)的二烷(10mL)/H2O(10mL)的溶液。向此溶液加入硼酸化合物36(682mg,1.37mmol)、二溴化合物35(295mg,0.546mmol),随后加入Pd(PPh3)4(60mg,0.0500mmol)。将反应置于惰性氮气气氛下,并温和加热回流24小时。使混合物冷却至RT,用CH2Cl2(50mL)稀释,并用H2O(50mL)洗涤。水层用CH2Cl2(2×50mL)萃取,合并的有机层经MgSO4干燥。粗产物通过SiO2层析,用3%MeOH/CH2Cl2洗脱,得到产物,为白色泡沫状物。收率602mg,85%。1H NMR(400MHz,CD2Cl2,25℃)δ7.36(m,5H),7.62(m,14H),7.77(m,13H),7.97(m,19H),8.04(m,4H),8.57(s,5H),8.91(m,5H)。
实施例22:合成化合物8
用氮气吹扫含Na2CO3(4.24g)的THF(20mL)/H2O(20mL)的溶液。向此溶液加入硼酸酯化合物29(2.60g,4.43mmol),3,5-二溴吡啶(473mg,2.00mmol),随后加入Pd(PPh3)4(204mg,0.177mmol)。将反应置于惰性氮气气氛下,并加热回流12小时。将混合物冷却至RT,并使各层分离。有机层用NaHCO3(1×100mL)洗涤,经Na2SO4干燥,并浓缩至干。滤饼用5%MeOH/CH2Cl2洗涤,将滤液浓缩至干,得到泡沫状物。粗物质通过SiO2层析,用5%MeOH/CH2Cl2洗脱,得到产物,为白色泡沫状物。收率1.56g,78%。1H NMR(400MHz,CD2Cl2,25℃)δ7.39(m,4H),7.64(m,10H),7.76(m,8H),7.98(m,14H),8.04(t,2H),8.25(t,1H),8.58(m,4H),8.93(m,6H)。
实施例23:合成化合物14
将100mL两颈圆底烧瓶包以锡箔,并装配搅拌棒、配有氮气入口管的回流冷凝器和塞子。向烧瓶加入化合物25(0.675g,1.25mmol)、9-(4-甲氧基苯基)-3,6-二(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)-9H-咔唑(0.263g,0.5mmol)、1,4-二烷(20mL)和四(三苯基膦)合钯(30mg,0.025mmol)。在反应过程中使装置保持在氮气气氛下。在室温搅拌混合物20分钟,然后通过漏斗加入溶于蒸馏水(4mL)的碳酸钾(0.4g,2.84mmol)。搅拌反应混合物,并在油浴中加热回流20小时,然后冷却到环境温度。通过漏斗加入蒸馏水(30mL),所得混合物在布氏漏斗上过滤。将滤液转移到分液漏斗,并用CH2Cl2(3×30mL)萃取。合并的有机相经Na2SO4干燥,在滤纸上过滤,通过旋转蒸发浓缩至干(30℃,25mmHg)。然后通过柱层析在硅胶上纯化(EtOAc/THF=6∶1),得到化合物14(0.24g,40%)。1H NMR(400MHz,CDCl3)δ8.93(br s,4H),8.62(br s,4H),8.49(m,2H),8.05(m,2H),7.96-7.90(m,14H),7.77-7.39(m,28H),7.17(m,2H),3.96(s,3H)。
实施例24:合成化合物16
向装配有磁力搅拌棒的25mL圆底烧瓶加入1,4-二烷(10mL)。将化合物28(0.365g,0.66mmol)、1,3,5-三(溴甲基)-2,4,6-三甲基苯(0.075g,0.189mmol)和碳酸钾(0.182g,1.34mmol)的混合物溶于溶剂。在氮气下使反应回流过夜。使反应混合物冷却到室温,并用CH2Cl2稀释。合并的有机相经Na2SO4干燥,在滤纸上过滤,通过旋转蒸发浓缩至干(30℃,25mmHg)。所得黄色固体通过柱层析(SiO2;乙酸乙酯/THF(V/V:4/1)作为洗脱液)纯化,得到化合物16,为白色固体(0.29,85%)。1H NMR(400MHz,CDCl3)δ8.97(s,6H),8.65(s,6H),7.99(d,6H),7.90(m,18H),7.77(m,6H),7.70(d,6H),7.63(m,15H),7.55(t,3H),7.43(t,6H),7.34(t,3H),7.21(m,6H),6.91(d,3H),5.32(S,6H),1.9(s,9H)。
实施例25:合成化合物38
将3.4g螺联茚满四酚(10mmol)加入4g(24.8mmol)六甲基二硅氮烷,并在120-125℃回流过夜。它开始作为悬浮液,在约1小时后变成澄清溶液。通过蒸馏去除过量的六甲基二硅氮烷。1H NMR(CDCl3):6.6(s,2H),6.2(s,2H),2.2(dd,4H),1.34(s,6H),1,30(s,6H),0.24(s,18H),0.18(s,18H)。
实施例26:合成化合物17
在室温下,在三颈圆底烧瓶中混合0.19g(0.3419mmol)邻-氟-STPPB(化合物27)和0.047g(0.0747mmol)甲硅烷基化四酚(化合物38)。向此烧瓶加入3mL无水DMF和3mL无水甲苯。在氩气流下将烧瓶加热到130℃。在除去甲苯后,然后,加入很少量的无水CsF(约5mg)。使温度升高到140℃。通过硅胶TLC监控反应。在4天后加入0.075g邻-氟-STPPB和2mL甲苯。在另外两天后停止反应。在反应混合物冷却至室温后,将其倒入10mL水中。用二氯甲烷(5mL)萃取固体。有机层用水5mL(×2)、盐水(×1)洗涤,经MgSO4干燥。在旋转蒸发器上除去溶剂。粗产物用THF/Hex(1/1-8/1)作为洗脱液通过硅胶柱分离。得到约~100mg淡黄色固体。使固体溶于CH2Cl2,加入己烷,直至出现白色固体。通过细玻璃料,经抽滤收集0.048g很细的白色固体。然后,尽量使白色固体重新溶于乙醇,加入少量CH2Cl2,以帮助溶解。在过夜后出现一些粉末,但全部粘在烧瓶壁上。从上清液收集8mg产物。1H NMR(CDCl3):8.90(d,8H),8.61(t,8H),8.37(d,4H),7.99-7.26(m,68H),6.94(s,2H),7.12(s,2H),6.8(dd,4H),2.48(dd,4H),1.45(s,6H),1.43(s,6H)。Maldi(M+=2482.2286)。
虽然,本文只举例说明和描述本发明的某些特征,但本领域的技术人员会想到很多修改和变化。因此,应理解,附加权利要求将覆盖落在本发明真实精神范围内的所有此类修改和变化。
Claims (14)
2.权利要求1的化合物,所述化合物具有下式
3.权利要求1的化合物,其中Ar1为直接键。
10.权利要求8的光电子器件,所述光电子器件为有机发光器件。
11.权利要求10的光电子器件,所述光电子器件包括含至少一种式I的化合物的电子传输层。
12.权利要求10的光电子器件,所述光电子器件包括含至少一种式I的化合物的空穴传输层。
13.权利要求10的光电子器件,所述光电子器件包括含至少一种式I的化合物的发射层。
14.权利要求8的光电子器件,所述光电子器件另外包含至少一种蓝色、黄色、橙色或红色磷光染料或其组合。
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CN108713051A (zh) * | 2016-02-04 | 2018-10-26 | 三星Sdi株式会社 | 有机光电元件用化合物、有机光电元件以及显示元件 |
US11177441B2 (en) | 2014-01-24 | 2021-11-16 | Samsung Sdi Co., Ltd. | Organic compound, composition, organic optoelectronic device, and display device |
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US8691399B2 (en) | 2009-01-08 | 2014-04-08 | General Electric Company | Electron-transporting materials and processes for making the same |
US7989476B2 (en) * | 2009-01-08 | 2011-08-02 | General Electric Company | Electron-transporting materials and processes for making the same |
US8178682B2 (en) * | 2009-06-26 | 2012-05-15 | General Electric Company | Process for making organic compounds and the organic compounds made therefrom |
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TWI404790B (zh) * | 2010-09-13 | 2013-08-11 | E Ray Optoelectronics Tech Co | Red phosphorescent materials and organic electroluminescent photodiodes |
US9515283B2 (en) | 2012-08-29 | 2016-12-06 | Boe Technology Group Co., Ltd. | OLED devices with internal outcoupling |
JP6074766B2 (ja) * | 2013-02-18 | 2017-02-08 | 国立大学法人山形大学 | 3,5−ジピリジルフェニル誘導体、それよりなる電子輸送材料及びそれを用いた有機エレクトロルミネッセンス素子 |
CN111892531B (zh) * | 2020-09-08 | 2021-10-01 | 长春海谱润斯科技股份有限公司 | 一种有机化合物及其有机电致发光器件 |
Family Cites Families (14)
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US6309763B1 (en) | 1997-05-21 | 2001-10-30 | The Dow Chemical Company | Fluorene-containing polymers and electroluminescent devices therefrom |
JPH10338872A (ja) | 1997-06-09 | 1998-12-22 | Tdk Corp | 色変換材料およびこれを用いた有機elカラーディスプレイ |
GB9813326D0 (en) | 1998-06-19 | 1998-08-19 | Cambridge Display Tech Ltd | Backlit displays |
JP3925265B2 (ja) * | 2002-03-25 | 2007-06-06 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子及びそれを用いた表示装置 |
US7056600B2 (en) | 2002-08-23 | 2006-06-06 | Agfa Gevaert | Layer configuration comprising an electron-blocking element |
EP1672961B1 (en) * | 2003-07-31 | 2014-12-03 | Mitsubishi Chemical Corporation | Compound, charge transport material and organic electroluminescent device |
CN101638380A (zh) * | 2003-07-31 | 2010-02-03 | 三菱化学株式会社 | 化合物、电荷传输材料和有机电致发光元件 |
JP4907912B2 (ja) | 2005-07-08 | 2012-04-04 | ケミプロ化成株式会社 | 新規な1,3,5−トリフェニルベンゼン誘導体およびそれを含む有機エレクトロルミネッセンス素子 |
US20080061686A1 (en) | 2006-03-22 | 2008-03-13 | Jie Liu | Phosphorescent light-emitting materials and methods of preparing |
KR20070101984A (ko) | 2006-04-13 | 2007-10-18 | 삼성에스디아이 주식회사 | 전하분리층을 구비한 유기 전기발광 소자 |
JP4960045B2 (ja) | 2006-09-04 | 2012-06-27 | ケミプロ化成株式会社 | 新規なビフェニル中心骨格を有するヘテロアリール系化合物およびそれを含む有機エレクトロルミネッセンス素子 |
CN101469041B (zh) * | 2007-12-25 | 2011-07-27 | 通用电气公司 | 含苯吡啶单元的聚合物 |
CN101469038B (zh) * | 2007-12-25 | 2012-03-28 | 通用电气公司 | 含苯吡啶单元的聚合物 |
US8039125B2 (en) * | 2008-05-22 | 2011-10-18 | General Electric Company | Compound comprising phenyl pyridine units |
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US10784447B2 (en) | 2015-04-24 | 2020-09-22 | Samsung Sdi Co., Ltd. | Organic compound, composition, and organic optoelectronic diode |
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