JP2009514812A - 新規のビナフタレン誘導体、その製造方法およびそれを用いた有機電子素子 - Google Patents
新規のビナフタレン誘導体、その製造方法およびそれを用いた有機電子素子 Download PDFInfo
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- JP2009514812A JP2009514812A JP2008536502A JP2008536502A JP2009514812A JP 2009514812 A JP2009514812 A JP 2009514812A JP 2008536502 A JP2008536502 A JP 2008536502A JP 2008536502 A JP2008536502 A JP 2008536502A JP 2009514812 A JP2009514812 A JP 2009514812A
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 296
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N 1-naphthalen-1-ylnaphthalene Chemical class C1=CC=C2C(C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 238000002347 injection Methods 0.000 claims abstract description 46
- 239000007924 injection Substances 0.000 claims abstract description 46
- 230000005525 hole transport Effects 0.000 claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims description 337
- 239000010410 layer Substances 0.000 claims description 120
- 239000012044 organic layer Substances 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 19
- -1 naphthol derivative compound Chemical class 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000001769 aryl amino group Chemical group 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000002560 nitrile group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000005621 boronate group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 125000005264 aryl amine group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 108091008695 photoreceptors Proteins 0.000 claims description 3
- DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical class C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-UHFFFAOYSA-N 0.000 claims description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- NWKPJILKQAAHQA-UHFFFAOYSA-N naphthalen-1-yl 2,2,2-trifluoroacetate Chemical class C1=CC=C2C(OC(=O)C(F)(F)F)=CC=CC2=C1 NWKPJILKQAAHQA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 description 59
- 239000000463 material Substances 0.000 description 50
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
- 230000032258 transport Effects 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 28
- 239000000203 mixture Substances 0.000 description 28
- 125000001624 naphthyl group Chemical group 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- 238000000034 method Methods 0.000 description 16
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- YLDFTMJPQJXGSS-UHFFFAOYSA-N 6-bromo-2-naphthol Chemical compound C1=C(Br)C=CC2=CC(O)=CC=C21 YLDFTMJPQJXGSS-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
- 230000005684 electric field Effects 0.000 description 14
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 13
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000012790 confirmation Methods 0.000 description 10
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 238000000151 deposition Methods 0.000 description 8
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- 239000000758 substrate Substances 0.000 description 8
- 238000001771 vacuum deposition Methods 0.000 description 8
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 0 *=C(C=Cc1ccccc1)c1c(cccc2)c2cc2ccccc12 Chemical compound *=C(C=Cc1ccccc1)c1c(cccc2)c2cc2ccccc12 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 5
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- 238000010992 reflux Methods 0.000 description 5
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- 239000007787 solid Substances 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000010405 anode material Substances 0.000 description 4
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- 238000001816 cooling Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 3
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 3
- LWLSVNFEVKJDBZ-UHFFFAOYSA-N N-[4-(trifluoromethoxy)phenyl]-4-[[3-[5-(trifluoromethyl)pyridin-2-yl]oxyphenyl]methyl]piperidine-1-carboxamide Chemical compound FC(OC1=CC=C(C=C1)NC(=O)N1CCC(CC1)CC1=CC(=CC=C1)OC1=NC=C(C=C1)C(F)(F)F)(F)F LWLSVNFEVKJDBZ-UHFFFAOYSA-N 0.000 description 3
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- LJHFUFVRZNYVMK-CYBMUJFWSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-[(3R)-3-hydroxypyrrolidin-1-yl]methanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C=CC=1)C(=O)N1C[C@@H](CC1)O LJHFUFVRZNYVMK-CYBMUJFWSA-N 0.000 description 3
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- YIWGJFPJRAEKMK-UHFFFAOYSA-N 1-(2H-benzotriazol-5-yl)-3-methyl-8-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carbonyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound CN1C(=O)N(c2ccc3n[nH]nc3c2)C2(CCN(CC2)C(=O)c2cnc(NCc3cccc(OC(F)(F)F)c3)nc2)C1=O YIWGJFPJRAEKMK-UHFFFAOYSA-N 0.000 description 2
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- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 2
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- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having a potential-jump barrier or a surface barrier
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
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- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
- C07C13/567—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered with a fluorene or hydrogenated fluorene ring system
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- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
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- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
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- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/56—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed
- C07C15/58—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed containing two rings
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
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- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/58—Naphthylamines; N-substituted derivatives thereof
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Abstract
Description
R1およびR2は同時にまたは各々独立して置換または非置換されたアルケニル基、置換または非置換されたアリール基、置換または非置換されたヘテロ芳香族基、置換または非置換されたアリールアミノ基からなる群から選択され、R1およびR2のうちの1つは水素であり得る。
MS[M+H]+=271
MS[M+H]+=459
MS[M+H]+=447
MS[M+H]+=573
MS[M+H]+=345
MS[M+H]+=589
MS[M+H]+=287
MS[M+H]+=403
MS[M+H]+=555
MS[M+H]+=543
MS[M+H]+=669
MS[M+H]+=441
MS[M+H]+=685
MS[M+H]+=479
MS[M]+=259
MS[M]+=399
MS:[M−H2O]+=398
前記化学式B−10−1の化合物(6.6g、15.9mmol)とベンゼン(100mL)を混ぜ、CF3SO3H(1.6mL、18.4mmol)を添加して、80℃で6時間還流(reflux)した。Ice−bathを用いて0℃に冷却した後、反応溶液に飽和NaHCO3水溶液を添加した。水とエチルアセテートで層を分離した後、有機層を分離して無水マグネシウムで乾燥させた。次に、前記有機層を真空減圧した後、THF/Hexaneで再結晶して化合物B−10(7.0g、収率93%)の化合物を製造した。
MS:[M]+=476
MS[M]+=523
MS[M+H]+=587
MS[M+H]+=683
MS[M+H]+=299
MS[M+H]+=395
MS[M+H]+=463
MS[M+H]+=559
MS[M+H]+=243
MS[M]+=321
MS[M+H]+=381
MS[M+H]+=569
MS[M+H]+=557
MS[M+H]+=683
MS[M+H]+=455
MS[M+H]+=699
MS[M]+=697
MS[M]+=279
前記で製造した化合物C−8−1である2−(6−ブロモナフタレン)−1,3−ジオキソラン(5g、17.9mmol)を乾燥THF(60mL)を加えて溶かした後、窒素の雰囲気下、−78℃でn−BuLi(26.9mmol、2.5Mヘキサン溶液内10.7mL)を滴加した。混合物を約1時間攪拌した後、トリメチルボレート(6.2mL、53.7mmol)を−78℃で滴加した。約30分後、冷却容器を除去し、混合物を室温で約3時間攪拌した。前記混合物に1N HCl(80mL)を加えてエチルアセテートで抽出した。有機層を硫酸マグネシウム上で乾燥して真空濃縮させた。粗生成物を石油エーテル内でスラリー化して吸引濾過し、乾燥して、2−(6−ホルミルナフタレン)ボロン酸化合物C−8を製造した(2.07g、収率57.8%)
MS[M+H]+=397
MS[M+H]+=699
MS[M+H]+=507
MS[M+H]+=695
MS[M+H]+=761
化合物2−41の合成資料は図5に示す。
MS[M+H]+=1013
MS[M+H]+=573
化合物1−157の合成資料は図6に示す。
MS[M+H]+=699
化合物1−173の合成資料は図7に示す。
MS[M+H]+=699
化合物1−166の合成資料は図8に示す。
MS[M+H]+=647
化合物2−44の合成資料は図9に示す。
MS[M+H]+=633
化合物1−70の合成資料は図10に示す。
MS[M+H]+=633
化合物1−71の合成資料は図11に示す。
MS[M+H]+=683
化合物1−72の合成資料は図12に示す。
MS[M+H]+=722
MS[M+H]+=823
化合物1−18の合成資料は図13に示す。
MS[M+H]+=889
MS[M+H]+=633
MS[M+H]+=639
Tm;306.5度
Tg;130.9度
化合物2−8の合成資料は図14に示す。
MS[M+H]+=875
MS[M+H]+=848
MS[M+H]+=1111
MS[M+H]+=859
MS[M+H]+=735
MS[M+H]+=611
MS[M+H]+=841
前記製造例に記載したように、色々な中間体を合成することができ、前記実施例に記載したように、上記のように合成された中間体の多様な組み合わせを通じて、Pd触媒下で、表1および表2に記載された多様な誘導体を製造することができる。
ITO(indium tin oxde)が1500Å厚さで薄膜コーティングされたガラス基板を洗剤を溶かした蒸溜水に入れて超音波で洗浄した。この時、洗剤としてはフィッシャー(Fischer Co.)社の製品を用い、蒸溜水としてはミリポア(Millipore Co.)社製のフィルタで2次濾過した蒸留水を用いた。ITOを30分間洗浄した後、蒸溜水で2回繰り返して超音波洗浄を10分間進行した。蒸溜水の洗浄が終わった後、イソプロピルアルコール、アセトン、メタノールの溶剤で超音波洗浄を行って乾燥させた後、プラズマ洗浄機に輸送させた。酸素プラズマを用いて前記基板を5分間洗浄した後、真空蒸着機に基板を輸送させた。
実験例1のように準備したITO電極上にヘキサニトリルヘキサアザトリフェニレン(500Å)、4,4’−ビス[N−(1−ナフチル)−N−フェニルアミノ]ビフェニル(NPB)400Å、Alq3(300Å)、および実施例1−4で製造した化合物1−157(300Å)、フッ化リチウム(LiF)12Åを順次熱真空蒸着して、正孔注入層、正孔輸送層、発光層、電子輸送層、および電子注入層を順に形成させた。その上に2000Å厚さのアルミニウムを蒸着して陰極を形成し、有機発光素子を製造した。
実験例1のように準備したITO電極上にヘキサニトリルヘキサアザトリフェニレン(500Å)、4,4’−ビス[N−(1−ナフチル)−N−フェニルアミノ]ビフェニル(NPB)400Å、Alq3(300Å)、および実施例1−6で製造した化合物1−166(300Å)、フッ化リチウム(LiF)12Åを順次熱真空蒸着して、正孔注入層、正孔輸送層、発光層、電子輸送層、および電子注入層を順に形成させた。その上に2000Å厚さのアルミニウムを蒸着して陰極を形成し、有機発光素子を製造した。
実験例1のように準備したITO電極上にヘキサニトリルヘキサアザトリフェニレン(500Å)、4,4’−ビス[N−(1−ナフチル)−N−フェニルアミノ]ビフェニル(NPB)400Å、Alq3(300Å)、および実施例2−4で製造した化合物2−8(300Å)、フッ化リチウム(LiF)12Åを順次熱真空蒸着して、正孔注入層、正孔輸送層、発光層、電子輸送層、および電子注入層を順に形成させた。その上に2000Å厚さのアルミニウムを蒸着して陰極を形成し、有機発光素子を製造した。
実験例1のように準備したITO電極上にヘキサニトリルヘキサアザトリフェニレン(500Å)、4,4’−ビス[N−(1−ナフチル)−N−フェニルアミノ]ビフェニル(NPB)400Å、Alq3(300Å)、および実施例1−7で製造した化合物2−44(300Å)、フッ化リチウム(LiF)12Åを順次熱真空蒸着して、正孔注入層、正孔輸送層、発光層、電子輸送層、および電子注入層を順に形成させた。その上に2000Å厚さのアルミニウムを蒸着して陰極を形成し、有機発光素子を製造した。
実験例1のように準備したITO電極上にヘキサニトリルヘキサアザトリフェニレン(500Å)、4,4’−ビス[N−(1−ナフチル)−N−フェニルアミノ]ビフェニル(NPB)400Å、実施例1−9で製造した化合物1−71(300Å)、Alq3(300Å)、およびフッ化リチウム(LiF)12Åを順次熱真空蒸着して、正孔注入層、正孔輸送層、発光層、電子輸送層、および電子注入層を順に形成させた。その上に2000Å厚さのアルミニウムを蒸着して陰極を形成し、有機発光素子を製造した。
実験例1のように準備したITO電極上にヘキサニトリルヘキサアザトリフェニレン(500Å)、4,4’−ビス[N−(1−ナフチル)−N−フェニルアミノ]ビフェニル(NPB)400Å、実施例1−10で製造した化合物1−72(300Å)、Alq3(300Å)、およびフッ化リチウム(LiF)12Åを順次熱真空蒸着して、正孔注入層、正孔輸送層、発光層、電子輸送層、および電子注入層を順に形成させた。その上に2000Å厚さのアルミニウムを蒸着して陰極を形成し、有機発光素子を製造した。
Claims (16)
- 前記置換または非置換されたアルケニル基が、置換または非置換されたC6〜C30のアリール基または置換または非置換されたC5〜C30のヘテロアリール基で置換または非置換されたアルケニル基である、請求項1に記載のビナフタレン誘導体。
- 前記置換または非置換されたアリール基が、ハロゲン、アミノ基、ニトリル基、ニトロ基、アルキルボロネート基、C1〜C30のアルキル基、C2〜C40のアルケニル基、C1〜C40のアルコキシ基、C3〜C30のシクロアルキル基、C3〜C30のヘテロシクロアルキル基、C6〜C30のアリール基、C5〜C30のヘテロアリール基、およびC6〜C30のアリールアミノ基からなる群から選択された1つ以上の基で置換または非置換されたC6〜C30のアリール基である、請求項1に記載のビナフタレン誘導体。
- 前記置換または非置換されたヘテロ芳香族基が、ハロゲン、アミノ基、ニトリル基、ニトロ基、アルキルボロネート基、C1〜C30のアルキル基、C2〜C40のアルケニル基、C1〜C40のアルコキシ基、C3〜C30のシクロアルキル基、C3〜C30のヘテロシクロアルキル基、C6〜C30のアリール基、C5〜C30のヘテロアリール基、およびC6〜C30のアリールアミノ基からなる群から選択された1つ以上の基で置換または非置換されたC5〜C30のヘテロ芳香族基である、請求項1に記載のビナフタレン誘導体。
- 前記置換または非置換されたアリールアミノ基が、ハロゲン、アミノ基、ニトリル基、ニトロ基、アルキルボロネート基、C1〜C30のアルキル基、C2〜C40のアルケニル基、C1〜C40のアルコキシ基、C3〜C30のシクロアルキル基、C3〜C30のヘテロシクロアルキル基、C6〜C30のアリール基、C5〜C30のヘテロアリール基、およびC6〜C30のアリールアミノ基からなる群から選択された1つ以上の基で置換または非置換されたC6〜C30のアリールアミノ基である、請求項1に記載のビナフタレン誘導体。
- 前記置換または非置換されたアリールアミノ基が、置換または非置換されたカルバゾール基である、請求項5に記載のビナフタレン誘導体。
- 前記化学式1のうちのR1またはR2が下記構造式から選択される、請求項1に記載のビナフタレン誘導体。
X、X1、X2、およびX3は各々独立して同一であるか異なり、水素、置換または非置換されたアルキル基、置換または非置換されたアルコキシ基、置換または非置換されたアルケニル基、置換または非置換されたアリール基、置換または非置換されたアリールアミン基、置換または非置換された複素環基、置換または非置換された脂環式基、置換または非置換されたシリコン基、置換または非置換されたホウ素基、置換または非置換されたアミノ基、ニトリル基、ニトロ基、ハロゲン基、置換または非置換されたアミド基、および置換または非置換されたエステル基からなる群から選択され、ここで、これらは互いに隣接する基と脂肪族、芳香族または複素環を形成することができる。] - 請求項1のビナフタレン誘導体の製造方法であって、
(a)塩基下でナフトール誘導体化合物にトリフルオロ酢酸無水物を反応させるステップと、
(b)前記(a)ステップで得られた化合物とナフタレンボロンエステル化合物またはナフタレンボロン酸化合物をパラジウム[II]触媒および塩基の存在下で鈴木カップリング反応させるステップとを含んでなる、製造方法。 - 請求項1のビナフタレン誘導体の製造方法であって、
(a)塩基下でナフトール誘導体化合物にトリフルオロ酢酸無水物を反応させるステップと、
(b)前記(a)ステップで得られた化合物とビスピナコラトジボラン試薬をパラジウム[II]触媒および塩基の存在下で反応させるステップと、
(c)前記(b)ステップで得られた化合物とブロモナフタレン誘導体またはトリフルオロアセトキシナフタレン誘導体をパラジウム[II]触媒および塩基の存在下で鈴木カップリング反応させるステップとを含んでなる、製造方法。 - 第1電極と、第2電極と、および第1電極と第2電極との間に配置された1層以上の有機物層とを備えてなる有機電子素子であって、
前記有機物層のうちの1層以上が請求項1に記載された化合物を含んでなる有機電子素子。 - 前記有機物層が正孔注入層および正孔輸送層を備えてなり、
前記正孔注入層および正孔輸送層が請求項1の化合物を含んでなる、請求項12に記載の有機電子素子。 - 前記有機物層が発光層を備えてなり、
前記発光層が請求項1の化合物を含んでなる、請求項12に記載の有機電子素子。 - 前記有機物層が電子輸送層をそなえてなり、
前記電子輸送層が請求項1の化合物を含んでなる、請求項12に記載の有機電子素子。 - 前記有機電子素子が、有機発光素子、有機太陽電池、有機感光体(OPC)、および有機トランジスタからなる群から選択されるものである、請求項12に記載の有機電子素子。
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JP4991737B2 (ja) | 2012-08-01 |
WO2007046658A1 (en) | 2007-04-26 |
KR100958000B1 (ko) | 2010-05-17 |
EP1937616A1 (en) | 2008-07-02 |
KR20070043666A (ko) | 2007-04-25 |
KR20080103953A (ko) | 2008-11-28 |
US20140183505A1 (en) | 2014-07-03 |
EP1937616A4 (en) | 2010-06-30 |
EP1937616B1 (en) | 2014-12-17 |
TW200728250A (en) | 2007-08-01 |
TWI313675B (en) | 2009-08-21 |
KR100878115B1 (ko) | 2009-01-14 |
US8951831B2 (en) | 2015-02-10 |
US20070108892A1 (en) | 2007-05-17 |
CN101291897A (zh) | 2008-10-22 |
CN101291897B (zh) | 2012-09-05 |
US8674138B2 (en) | 2014-03-18 |
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