JP3127013B2 - シクロヘキシルフェニルピリミジン、製造方法及び液晶混合物への使用 - Google Patents
シクロヘキシルフェニルピリミジン、製造方法及び液晶混合物への使用Info
- Publication number
- JP3127013B2 JP3127013B2 JP03249736A JP24973691A JP3127013B2 JP 3127013 B2 JP3127013 B2 JP 3127013B2 JP 03249736 A JP03249736 A JP 03249736A JP 24973691 A JP24973691 A JP 24973691A JP 3127013 B2 JP3127013 B2 JP 3127013B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- pyrimidine
- mol
- alkyl
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims description 86
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 77
- BOOGLODHTHQEQO-UHFFFAOYSA-N 4-cyclohexyl-2-phenylpyrimidine Chemical compound C1CCCCC1C1=CC=NC(C=2C=CC=CC=2)=N1 BOOGLODHTHQEQO-UHFFFAOYSA-N 0.000 title claims description 25
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 28
- -1 2 - cyclohexyl phenyl Chemical group 0.000 claims description 25
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims 1
- 238000002844 melting Methods 0.000 description 30
- 230000008018 melting Effects 0.000 description 30
- 239000004990 Smectic liquid crystal Substances 0.000 description 9
- ATZLPEPWPJQANQ-UHFFFAOYSA-N 2-(4-hexoxyphenyl)-5-octylpyrimidine Chemical compound N1=CC(CCCCCCCC)=CN=C1C1=CC=C(OCCCCCC)C=C1 ATZLPEPWPJQANQ-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- CZVGOAPQSLSDNN-UHFFFAOYSA-N 2-(4-decoxyphenyl)-5-octylpyrimidine Chemical compound C1=CC(OCCCCCCCCCC)=CC=C1C1=NC=C(CCCCCCCC)C=N1 CZVGOAPQSLSDNN-UHFFFAOYSA-N 0.000 description 7
- 230000007704 transition Effects 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- IBYIRCIVTGUDNK-UHFFFAOYSA-N 2-(4-butoxyphenyl)-5-octoxypyrimidine Chemical compound N1=CC(OCCCCCCCC)=CN=C1C1=CC=C(OCCCC)C=C1 IBYIRCIVTGUDNK-UHFFFAOYSA-N 0.000 description 5
- XYGUNTNTTDQAGL-UHFFFAOYSA-N 2-(4-decoxyphenyl)-5-octoxypyrimidine Chemical compound C1=CC(OCCCCCCCCCC)=CC=C1C1=NC=C(OCCCCCCCC)C=N1 XYGUNTNTTDQAGL-UHFFFAOYSA-N 0.000 description 5
- HOAGGFRICQSSLG-UHFFFAOYSA-N 2-(4-hexoxyphenyl)-5-octoxypyrimidine Chemical compound N1=CC(OCCCCCCCC)=CN=C1C1=CC=C(OCCCCCC)C=C1 HOAGGFRICQSSLG-UHFFFAOYSA-N 0.000 description 5
- YSLLSTYBZAIXMY-UHFFFAOYSA-N 2-(4-octoxyphenyl)-5-octylpyrimidine Chemical compound C1=CC(OCCCCCCCC)=CC=C1C1=NC=C(CCCCCCCC)C=N1 YSLLSTYBZAIXMY-UHFFFAOYSA-N 0.000 description 5
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical class C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 5
- IETWSNMXSKALFY-UHFFFAOYSA-N 5-octoxy-2-(4-octoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCCCC)=CC=C1C1=NC=C(OCCCCCCCC)C=N1 IETWSNMXSKALFY-UHFFFAOYSA-N 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 230000010287 polarization Effects 0.000 description 4
- 150000003230 pyrimidines Chemical class 0.000 description 4
- IJOCVWNDKBGLJR-WKILWMFISA-N CCCCC[C@H]1CC[C@@H](CC1)C(=O)Oc1ccccc1 Chemical compound CCCCC[C@H]1CC[C@@H](CC1)C(=O)Oc1ccccc1 IJOCVWNDKBGLJR-WKILWMFISA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- 230000002269 spontaneous effect Effects 0.000 description 3
- QQGCYEYOCMPRCB-UHFFFAOYSA-N 2-(4-dodecoxyphenyl)-5-octylpyrimidine Chemical compound C1=CC(OCCCCCCCCCCCC)=CC=C1C1=NC=C(CCCCCCCC)C=N1 QQGCYEYOCMPRCB-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- JUHKPXJMKBBWCL-UHFFFAOYSA-N 5-decyl-2-(4-hexoxyphenyl)pyrimidine Chemical compound N1=CC(CCCCCCCCCC)=CN=C1C1=CC=C(OCCCCCC)C=C1 JUHKPXJMKBBWCL-UHFFFAOYSA-N 0.000 description 2
- PYMMEHPLFYFSIW-UHFFFAOYSA-N [4-(5-octylpyrimidin-2-yl)phenyl] heptanoate Chemical compound N1=CC(CCCCCCCC)=CN=C1C1=CC=C(OC(=O)CCCCCC)C=C1 PYMMEHPLFYFSIW-UHFFFAOYSA-N 0.000 description 2
- MXZXNPLKHCPQTF-UHFFFAOYSA-N [4-(5-octylpyrimidin-2-yl)phenyl] octanoate Chemical compound N1=CC(CCCCCCCC)=CN=C1C1=CC=C(OC(=O)CCCCCCC)C=C1 MXZXNPLKHCPQTF-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- GRZJZRHVJAXMRR-UHFFFAOYSA-N 1-cyclohexyl-2-phenylbenzene Chemical group C1CCCCC1C1=CC=CC=C1C1=CC=CC=C1 GRZJZRHVJAXMRR-UHFFFAOYSA-N 0.000 description 1
- RZDNUOXSQJBPCI-UHFFFAOYSA-N 2-(4-butoxyphenyl)-5-octylpyrimidine Chemical compound N1=CC(CCCCCCCC)=CN=C1C1=CC=C(OCCCC)C=C1 RZDNUOXSQJBPCI-UHFFFAOYSA-N 0.000 description 1
- XHTWBPKQRJEYGJ-UHFFFAOYSA-N 2-(4-decoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCCCCCC)=CC=C1C1=NC=CC=N1 XHTWBPKQRJEYGJ-UHFFFAOYSA-N 0.000 description 1
- DCKBKOTWLPKZBD-UHFFFAOYSA-N 2-(4-dodecoxyphenyl)-5-octoxypyrimidine Chemical compound C1=CC(OCCCCCCCCCCCC)=CC=C1C1=NC=C(OCCCCCCCC)C=N1 DCKBKOTWLPKZBD-UHFFFAOYSA-N 0.000 description 1
- PHMRQMJVXACJHA-UHFFFAOYSA-N 2-(4-hexoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCC)=CC=C1C1=NC=CC=N1 PHMRQMJVXACJHA-UHFFFAOYSA-N 0.000 description 1
- VEVVGMKVNLDIBP-UHFFFAOYSA-N 2-[4-(6-cyclopropylhexoxy)phenyl]-5-octylpyrimidine Chemical compound N1=CC(CCCCCCCC)=CN=C1C(C=C1)=CC=C1OCCCCCCC1CC1 VEVVGMKVNLDIBP-UHFFFAOYSA-N 0.000 description 1
- RMNNHNYABBOSIW-UKILVPOCSA-N 2-[4-[(2s,3s)-3-butyl-2-methyloxiran-2-yl]oxyphenyl]-5-octylpyrimidine Chemical compound N1=CC(CCCCCCCC)=CN=C1C(C=C1)=CC=C1O[C@@]1(C)[C@H](CCCC)O1 RMNNHNYABBOSIW-UKILVPOCSA-N 0.000 description 1
- YPUSLQFSBBYBCE-UHFFFAOYSA-N 3-(dimethylamino)-2-phenylmethoxyprop-2-enal Chemical compound CN(C)C=C(C=O)OCC1=CC=CC=C1 YPUSLQFSBBYBCE-UHFFFAOYSA-N 0.000 description 1
- YHQOKFPEPNWEQH-ONJSCSTBSA-N 5-[4-[(5S)-3-methoxy-1,4-dioxaspiro[4.5]decan-6-yl]phenyl]-2-octoxypyrimidine Chemical compound COC1O[C@@]2(C(CCCC2)C2=CC=C(C=C2)C=2C=NC(=NC=2)OCCCCCCCC)OC1 YHQOKFPEPNWEQH-ONJSCSTBSA-N 0.000 description 1
- GFVBLGLZLGXIQX-UHFFFAOYSA-N 8-bromooctylcyclopropane Chemical compound BrCCCCCCCCC1CC1 GFVBLGLZLGXIQX-UHFFFAOYSA-N 0.000 description 1
- 241000282806 Rhinoceros Species 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 150000001840 cholesterol esters Chemical class 0.000 description 1
- 229940114081 cinnamate Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 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
- 239000012043 crude product Substances 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 125000006612 decyloxy group Chemical group 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/40—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals
- C09K19/406—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals containing silicon
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/345—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing two nitrogen atoms
- C09K19/3458—Uncondensed pyrimidines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/345—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing two nitrogen atoms
- C09K19/3458—Uncondensed pyrimidines
- C09K19/3466—Pyrimidine with at least another heterocycle in the chain
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/345—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing two nitrogen atoms
- C09K19/3458—Uncondensed pyrimidines
- C09K19/3469—Pyrimidine with a specific end-group other than alkyl, alkoxy or -C*-
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Liquid Crystal Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4030579A DE4030579A1 (de) | 1990-09-27 | 1990-09-27 | Cyclohexylphenylpyrimidine, verfahren zu ihrer herstellung und ihre verwendung in fluessigkristallinen mischungen |
| DE4030579:1 | 1990-09-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05255277A JPH05255277A (ja) | 1993-10-05 |
| JP3127013B2 true JP3127013B2 (ja) | 2001-01-22 |
Family
ID=6415104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP03249736A Expired - Fee Related JP3127013B2 (ja) | 1990-09-27 | 1991-09-27 | シクロヘキシルフェニルピリミジン、製造方法及び液晶混合物への使用 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US5200521A (enExample) |
| EP (1) | EP0477901A3 (enExample) |
| JP (1) | JP3127013B2 (enExample) |
| KR (1) | KR920006331A (enExample) |
| CA (1) | CA2052279A1 (enExample) |
| DE (1) | DE4030579A1 (enExample) |
| IE (1) | IE913386A1 (enExample) |
| NO (1) | NO913774L (enExample) |
| PT (1) | PT99089A (enExample) |
| TW (1) | TW223062B (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5407599A (en) * | 1987-11-25 | 1995-04-18 | Hoechst Aktiengesellschaft | Cyclopropylaklyl or -alkenyl or heterocyclic compounds, process for their preparation and their use in liquid-crystalline mixtures |
| DE4030579A1 (de) * | 1990-09-27 | 1992-04-02 | Hoechst Ag | Cyclohexylphenylpyrimidine, verfahren zu ihrer herstellung und ihre verwendung in fluessigkristallinen mischungen |
| EP1846330A4 (en) * | 2005-01-10 | 2009-12-23 | Univ North Dakota | OXIDATION OF MERCURY OF SMOKE USING A CATALYTIC BARRIER FILTER |
| PE20140417A1 (es) | 2011-02-15 | 2014-03-29 | Bayer Ip Gmbh | Combinaciones de compuestos activos |
| CN107286951B (zh) * | 2016-04-01 | 2019-01-29 | 北京八亿时空液晶科技股份有限公司 | 一种环丙基类负介电各向异性的液晶化合物及其应用 |
| CN107286952B (zh) * | 2016-04-01 | 2019-01-29 | 北京八亿时空液晶科技股份有限公司 | 一种环丙基类负介电各向异性的液晶化合物及其应用 |
| CN107345142B (zh) * | 2016-05-06 | 2020-02-21 | 北京八亿时空液晶科技股份有限公司 | 一种含有萘环的负介电各向异性液晶组合物及其应用 |
| CN107400516B (zh) * | 2016-05-19 | 2019-01-29 | 北京八亿时空液晶科技股份有限公司 | 一种环丙基类负介电各向异性的液晶化合物及其应用 |
| WO2025013902A1 (ja) * | 2023-07-11 | 2025-01-16 | 富士フイルム株式会社 | 組成物、光学異方性膜、化合物 |
| WO2025013901A1 (ja) * | 2023-07-11 | 2025-01-16 | 富士フイルム株式会社 | 液晶組成物、光学異方性層、硬化膜、回折素子、化合物 |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0084194B1 (de) * | 1982-01-14 | 1986-04-30 | MERCK PATENT GmbH | Flüssigkristallmischungen |
| JPS5939876A (ja) * | 1982-08-26 | 1984-03-05 | Chisso Corp | ピリミジン誘導体 |
| DE3315295A1 (de) * | 1983-04-27 | 1984-10-31 | Merck Patent Gmbh, 6100 Darmstadt | Fluorhaltige pyrimidinderivate |
| JPS6051778A (ja) * | 1983-08-31 | 1985-03-23 | Chisso Corp | 液晶組成物 |
| GB8400665D0 (en) * | 1984-01-11 | 1984-02-15 | Secr Defence | Disubstituted ethanes |
| DE3575158D1 (de) * | 1984-07-12 | 1990-02-08 | Hoffmann La Roche | Fluessigkristalline gemische enthaltend komponenten mit einer 4-alkenyl- oder 2z-alkenyl-seitenkette. |
| JPH0718995B2 (ja) * | 1985-02-19 | 1995-03-06 | キヤノン株式会社 | 液晶素子 |
| EP0263843B1 (en) * | 1986-02-21 | 1992-12-02 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern | Liquid crystal compounds, mixtures and devices |
| US4816178A (en) * | 1986-04-30 | 1989-03-28 | Canon Kabushiki Kaisha | Optically active compound and liquid crystal composition containing same |
| GB8615316D0 (en) * | 1986-06-23 | 1986-07-30 | Secr Defence | Chiral liquid crystal compounds |
| JPH062751B2 (ja) * | 1986-07-14 | 1994-01-12 | チッソ株式会社 | ２−（トランス−４−アルキルシクロヘキシル）−５−アルコキシピリミジン |
| JPH0749392B2 (ja) * | 1986-12-22 | 1995-05-31 | チッソ株式会社 | オメガ置換脂肪酸エステル骨格を有する光学活性化合物 |
| EP0285395B1 (en) * | 1987-03-31 | 1994-05-11 | Ajinomoto Co., Inc. | Phenyl-pyrimidine liquid crystal compounds and liquid crystal compositions containing the same |
| DE3852422T2 (de) * | 1987-04-27 | 1995-05-04 | Chisso Corp | Optisch aktive 2-Biphenylpyrimidinderivate und diese enthaltende Flüssigkristallmischungen. |
| JPH0730041B2 (ja) * | 1987-06-01 | 1995-04-05 | チッソ株式会社 | スメクチック性液晶化合物 |
| JPH0759567B2 (ja) * | 1987-07-15 | 1995-06-28 | 旭電化工業株式会社 | ピリミジン化合物 |
| JPH0692337B2 (ja) * | 1987-07-28 | 1994-11-16 | キヤノン株式会社 | 光学活性な液晶性化合物およびそれを含む液晶組成物 |
| JP2532886B2 (ja) * | 1987-09-08 | 1996-09-11 | チッソ株式会社 | ネマチツク液晶組成物 |
| EP0313284B1 (en) * | 1987-10-20 | 1994-07-27 | Chisso Corporation | 2,5-Diphenyl pyrimidine compounds and liquid crystal compositions containing them |
| JP2594583B2 (ja) * | 1987-11-10 | 1997-03-26 | シャープ株式会社 | 液晶表示装置 |
| JP2610467B2 (ja) * | 1987-11-12 | 1997-05-14 | キヤノン株式会社 | 液晶性化合物、それを含有する液晶組成物およびそれを使用した液晶素子 |
| CN1022409C (zh) * | 1987-11-25 | 1993-10-13 | 赫彻斯特股份公司 | 液晶环丙基烷基杂环化合物制备方法 |
| JP2792894B2 (ja) * | 1988-03-28 | 1998-09-03 | 昭和シェル石油株式会社 | ヘテロ環骨格を有する液晶物質 |
| JPH01275568A (ja) * | 1988-04-28 | 1989-11-06 | Showa Shell Sekiyu Kk | アジン誘導体 |
| EP0343487B1 (de) * | 1988-05-26 | 1993-01-20 | F. Hoffmann-La Roche Ag | Alpha-Fluorcarbonsäurecyclohexylester |
| JP2732269B2 (ja) * | 1988-10-27 | 1998-03-25 | 旭電化工業株式会社 | 光学活性エステル化合物および該化合物を含有する液晶組成物 |
| JPH02118618A (ja) * | 1988-10-28 | 1990-05-02 | Toshiba Corp | 液晶表示素子 |
| DE4030579A1 (de) * | 1990-09-27 | 1992-04-02 | Hoechst Ag | Cyclohexylphenylpyrimidine, verfahren zu ihrer herstellung und ihre verwendung in fluessigkristallinen mischungen |
-
1990
- 1990-09-27 DE DE4030579A patent/DE4030579A1/de not_active Withdrawn
-
1991
- 1991-09-09 TW TW080107119A patent/TW223062B/zh active
- 1991-09-25 EP EP19910116334 patent/EP0477901A3/de not_active Withdrawn
- 1991-09-25 KR KR1019910016637A patent/KR920006331A/ko not_active Ceased
- 1991-09-25 US US07/765,551 patent/US5200521A/en not_active Expired - Lifetime
- 1991-09-26 PT PT99089A patent/PT99089A/pt not_active Application Discontinuation
- 1991-09-26 IE IE338691A patent/IE913386A1/en unknown
- 1991-09-26 NO NO91913774A patent/NO913774L/no unknown
- 1991-09-26 CA CA002052279A patent/CA2052279A1/en not_active Abandoned
- 1991-09-27 JP JP03249736A patent/JP3127013B2/ja not_active Expired - Fee Related
-
1992
- 1992-08-19 US US07/932,065 patent/US5439612A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US5439612A (en) | 1995-08-08 |
| CA2052279A1 (en) | 1992-03-28 |
| US5200521A (en) | 1993-04-06 |
| DE4030579A1 (de) | 1992-04-02 |
| KR920006331A (ko) | 1992-04-27 |
| EP0477901A2 (de) | 1992-04-01 |
| JPH05255277A (ja) | 1993-10-05 |
| NO913774D0 (no) | 1991-09-26 |
| IE913386A1 (en) | 1992-04-08 |
| TW223062B (enExample) | 1994-05-01 |
| EP0477901A3 (en) | 1992-08-05 |
| NO913774L (no) | 1992-03-30 |
| PT99089A (pt) | 1992-08-31 |
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| Date | Code | Title | Description |
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| LAPS | Cancellation because of no payment of annual fees |