JP2011068591A - 4環性アジン化合物 - Google Patents
4環性アジン化合物 Download PDFInfo
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- JP2011068591A JP2011068591A JP2009220582A JP2009220582A JP2011068591A JP 2011068591 A JP2011068591 A JP 2011068591A JP 2009220582 A JP2009220582 A JP 2009220582A JP 2009220582 A JP2009220582 A JP 2009220582A JP 2011068591 A JP2011068591 A JP 2011068591A
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- 150000001875 compounds Chemical class 0.000 claims abstract description 50
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 33
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 13
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 12
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 9
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract description 8
- 239000000463 material Substances 0.000 abstract description 8
- 235000010290 biphenyl Nutrition 0.000 abstract description 4
- 239000004305 biphenyl Substances 0.000 abstract description 4
- 230000021615 conjugation Effects 0.000 abstract 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- -1 tolan compound Chemical class 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZBYNJMFPIWXPAQ-UHFFFAOYSA-N CCCC1=CC=C(C=C1)C2=CC(=C(C=C2)C=NN=CC3=C(C=C(C=C3)C4=CC=C(C=C4)CCC)F)F Chemical compound CCCC1=CC=C(C=C1)C2=CC(=C(C=C2)C=NN=CC3=C(C=C(C=C3)C4=CC=C(C=C4)CCC)F)F ZBYNJMFPIWXPAQ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical compound C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QDFKKJYEIFBEFC-UHFFFAOYSA-N 1-bromo-3-fluorobenzene Chemical compound FC1=CC=CC(Br)=C1 QDFKKJYEIFBEFC-UHFFFAOYSA-N 0.000 description 1
- ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 description 1
- BGVOIDLAUFLERQ-UHFFFAOYSA-N 1-fluoro-3-(4-methylphenyl)benzene Chemical group C1=CC(C)=CC=C1C1=CC=CC(F)=C1 BGVOIDLAUFLERQ-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- WSFOBHPKFHJZMC-UHFFFAOYSA-N 2-fluoro-4-(4-propylphenyl)benzaldehyde Chemical compound C1=CC(CCC)=CC=C1C1=CC=C(C=O)C(F)=C1 WSFOBHPKFHJZMC-UHFFFAOYSA-N 0.000 description 1
- JEAWWPCRZCCPKK-UHFFFAOYSA-N 3-fluoro-4-(4-propylphenyl)benzaldehyde Chemical compound C1=CC(CCC)=CC=C1C1=CC=C(C=O)C=C1F JEAWWPCRZCCPKK-UHFFFAOYSA-N 0.000 description 1
- SKACYTFVQMNOSX-UHFFFAOYSA-N CCC=CC1=CC(=C(C=C1)C2=CC=C(C=C2)C=NN=CC3=CC=C(C=C3)C4=C(C=C(C=C4)C=CCC)F)F Chemical compound CCC=CC1=CC(=C(C=C1)C2=CC=C(C=C2)C=NN=CC3=CC=C(C=C3)C4=C(C=C(C=C4)C=CCC)F)F SKACYTFVQMNOSX-UHFFFAOYSA-N 0.000 description 1
- QNFWELYWDGGFRY-UHFFFAOYSA-N CCC=CC1=CC(=C(C=C1)C2=CC=C(C=C2)C=O)F Chemical compound CCC=CC1=CC(=C(C=C1)C2=CC=C(C=C2)C=O)F QNFWELYWDGGFRY-UHFFFAOYSA-N 0.000 description 1
- LCLQIXHLLYMGSH-UHFFFAOYSA-N CCCC1=CC(=C(C=C1)C2=CC=C(C=C2)C=NN=CC3=CC=C(C=C3)C4=C(C=C(C=C4)CCC)F)F Chemical compound CCCC1=CC(=C(C=C1)C2=CC=C(C=C2)C=NN=CC3=CC=C(C=C3)C4=C(C=C(C=C4)CCC)F)F LCLQIXHLLYMGSH-UHFFFAOYSA-N 0.000 description 1
- YXPSHTIHXXKYCZ-UHFFFAOYSA-N CCCC1=CC=C(C=C1)C2=C(C=C(C=C2)C=NN=CC3=CC(=C(C=C3)C4=CC=C(C=C4)CCC)F)F Chemical compound CCCC1=CC=C(C=C1)C2=C(C=C(C=C2)C=NN=CC3=CC(=C(C=C3)C4=CC=C(C=C4)CCC)F)F YXPSHTIHXXKYCZ-UHFFFAOYSA-N 0.000 description 1
- SCZODYOJJRCEMF-UHFFFAOYSA-N CCCC1=CC=C(C=C1)C2=CC(=C(C=C2)C=NN=CC3=CC=C(C=C3)C4=CC(=C(C=C4)CCC)F)F Chemical compound CCCC1=CC=C(C=C1)C2=CC(=C(C=C2)C=NN=CC3=CC=C(C=C3)C4=CC(=C(C=C4)CCC)F)F SCZODYOJJRCEMF-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 238000005282 brightening Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000006138 lithiation reaction Methods 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
(実施例1) 1−[4−(4−プロピルフェニル)−2−フルオロベンジリデン]−2−[4−(4−プロピルフェニル)−2−フルオロベンジリデン]ヒドラジン(第1表中No.(I−1)の化合物)の合成
1H−NMR(400MHz、CDCl3)σ(ppm):0.98(t、6H),1.70(m、4H),2.65(t,4H)7.25−7.71(m、14H),8.66(s,2H)
また、上記において、3−フルオロ−4’プロピル−ビフェニル−4−カルバルデヒドに換えて、2−フルオロ−4’プロピル−ビフェニル−4−カルバルデヒド、2’−フルオロ−4’プロピル−ビフェニル−4−カルバルデヒド、
又は2’−フルオロ−4’ブテニル−ビフェニル−4−カルバルデヒド、
を用いることにより、以下の化合物を得た。
1−[4−(4プロピルフェニル)−3−フルオロベンジリデン]−2−[4−(4プロピルフェニル)−3−フルオロベンジリデン]ヒドラジン(第1表中No.(I−2)の化合物)
1−[4−(2−フルオロ−4プロピルフェニル)ベンジリデン]−2−[4−(2−フルオロ−4プロピルフェニル)ベンジリデン]ヒドラジン(第1表中No.(I−3)の化合物)
1−[4−(2−フルオロ−4ブテニルフェニル)ベンジリデン]−2−[4−(2−フルオロ−4ブテニルフェニル)ベンジリデン]ヒドラジン(第1表中No.(I−4)の化合物)
(実施例2)液晶組成物の調整
低粘性で、温度範囲の広いネマチック液晶として特にアクティブマトリックス駆動用に好適なホスト液晶(H)
(実施例3) 1−[4−(4−プロピルフェニル)−2−フルオロベンジリデン]−2−[4−(4−プロピル−3−フルオロフェニル)ベンジリデン]ヒドラジン(式(I−5)で表される化合物)の製造方法III
同様にして、一般式(I)の化合物(If)〜(Ig)、(Iw)〜(Iz)を製造することができる。
(比較例1)
式(A)
(比較例2)
式(B)
(比較例3)
更にΔnを大きくするため式(B)で表される化合物にベンゼン環を導入した式(B’)
Claims (6)
- 一般式(I)において、R又はR’のうち少なくとも一方が炭素原子数1〜12のアルキル基、炭素原子数1〜12のアルコキシル基、炭素原子数2〜12のアルケニル基又は炭素原子数2〜12のアルケニルオキシ基である請求項1記載の化合物。
- 一般式(I)において、X1〜X8のうち少なくとも1つがフッ素原子であり、X9〜X16のうち少なくとも1つがフッ素原子である請求項1又は2記載の化合物。
- 一般式(I)において、RとR’が同じ置換基を表し、X1とX15が同じ置換基を表し、X2とX16が同じ置換基を表し、X3とX13が同じ置換基を表し、X4とX14が同じ置換基を表し、X5とX11が同じ置換基を表し、X6とX12が同じ置換基を表し、X7とX9が同じ置換基を表し、及びX8とX10が同じ置換基を表す請求項1〜3のいずれかに記載の化合物。
- 請求項1〜4のいずれかに記載の一般式(I)で表される化合物を含有する液晶組成物。
- 請求項5に記載の液晶組成物を使用した液晶表示素子。
Priority Applications (1)
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JP2009220582A JP5545517B2 (ja) | 2009-09-25 | 2009-09-25 | 4環性アジン化合物 |
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JP2009220582A JP5545517B2 (ja) | 2009-09-25 | 2009-09-25 | 4環性アジン化合物 |
Publications (2)
Publication Number | Publication Date |
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JP2011068591A true JP2011068591A (ja) | 2011-04-07 |
JP5545517B2 JP5545517B2 (ja) | 2014-07-09 |
Family
ID=44014238
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JP2009220582A Active JP5545517B2 (ja) | 2009-09-25 | 2009-09-25 | 4環性アジン化合物 |
Country Status (1)
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JP (1) | JP5545517B2 (ja) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2013006979A (ja) * | 2011-06-24 | 2013-01-10 | Dic Corp | 誘電率異方性が負である液晶組成物、及び該液晶組成物を用いた液晶表示素子 |
CN103305234A (zh) * | 2013-06-08 | 2013-09-18 | 石家庄诚志永华显示材料有限公司 | 一种快速响应的液晶组合物 |
US10287501B2 (en) * | 2012-03-08 | 2019-05-14 | Tokyo Institute Of Technology | Liquid crystal display element |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH1171338A (ja) * | 1997-06-23 | 1999-03-16 | Dainippon Ink & Chem Inc | 3環性アジン |
JP2006089622A (ja) * | 2004-09-24 | 2006-04-06 | Chisso Corp | 高分子と光学活性な液晶材料からなる複合体 |
-
2009
- 2009-09-25 JP JP2009220582A patent/JP5545517B2/ja active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH1171338A (ja) * | 1997-06-23 | 1999-03-16 | Dainippon Ink & Chem Inc | 3環性アジン |
JP2006089622A (ja) * | 2004-09-24 | 2006-04-06 | Chisso Corp | 高分子と光学活性な液晶材料からなる複合体 |
Non-Patent Citations (1)
Title |
---|
JPN7013004466; 液晶の化学〔季刊 化学総説No.22〕 , 1994, 40-47 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2013006979A (ja) * | 2011-06-24 | 2013-01-10 | Dic Corp | 誘電率異方性が負である液晶組成物、及び該液晶組成物を用いた液晶表示素子 |
US10287501B2 (en) * | 2012-03-08 | 2019-05-14 | Tokyo Institute Of Technology | Liquid crystal display element |
CN103305234A (zh) * | 2013-06-08 | 2013-09-18 | 石家庄诚志永华显示材料有限公司 | 一种快速响应的液晶组合物 |
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