DE3909355A1 - Ferroelektrische fluessigkristalline mischungen - Google Patents
Ferroelektrische fluessigkristalline mischungenInfo
- Publication number
- DE3909355A1 DE3909355A1 DE3909355A DE3909355A DE3909355A1 DE 3909355 A1 DE3909355 A1 DE 3909355A1 DE 3909355 A DE3909355 A DE 3909355A DE 3909355 A DE3909355 A DE 3909355A DE 3909355 A1 DE3909355 A1 DE 3909355A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- optically active
- integer
- ferroelectric liquid
- component
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 115
- 239000007788 liquid Substances 0.000 title description 8
- 239000002019 doping agent Substances 0.000 claims abstract description 26
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 claims abstract description 24
- 150000002148 esters Chemical class 0.000 claims abstract description 19
- UJJLJRQIPMGXEZ-UHFFFAOYSA-N tetrahydro-2-furoic acid Chemical compound OC(=O)C1CCCO1 UJJLJRQIPMGXEZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000002170 ethers Chemical class 0.000 claims abstract description 6
- JRFVJVVAMLTIAP-UHFFFAOYSA-N 4-(1,3-dioxolan-4-yloxy)-1,3-dioxolane Chemical class O1COCC1OC1OCOC1 JRFVJVVAMLTIAP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- -1 pyrimidine-2,5-diyl Chemical group 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 5
- OTGHWLKHGCENJV-UHFFFAOYSA-N glycidic acid Chemical class OC(=O)C1CO1 OTGHWLKHGCENJV-UHFFFAOYSA-N 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 4
- 150000002989 phenols Chemical class 0.000 claims description 4
- HAIBGXNWAUQCEG-UHFFFAOYSA-N 1,3-dioxolane-4-carboxylic acid Chemical class OC(=O)C1COCO1 HAIBGXNWAUQCEG-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical class OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 3
- 150000004862 dioxolanes Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 150000003980 alpha-chlorocarboxylic acids Chemical class 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 150000003230 pyrimidines Chemical class 0.000 claims 1
- 230000010287 polarization Effects 0.000 abstract description 23
- 230000002269 spontaneous effect Effects 0.000 abstract description 23
- 238000002844 melting Methods 0.000 description 19
- 230000008018 melting Effects 0.000 description 19
- 230000003287 optical effect Effects 0.000 description 7
- 239000004990 Smectic liquid crystal Substances 0.000 description 6
- 239000004973 liquid crystal related substance Substances 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
- RVLAXPQGTRTHEV-UHFFFAOYSA-N 4-pentylcyclohexane-1-carboxylic acid Chemical compound CCCCCC1CCC(C(O)=O)CC1 RVLAXPQGTRTHEV-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
- 230000008901 benefit Effects 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- 238000000819 phase cycle Methods 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- UJJLJRQIPMGXEZ-SCSAIBSYSA-N tetrahydrofuran-2-carboxylic acid Chemical compound OC(=O)[C@H]1CCCO1 UJJLJRQIPMGXEZ-SCSAIBSYSA-N 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- RMNNHNYABBOSIW-ILBGXUMGSA-N 2-[4-[(2s,3r)-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-ILBGXUMGSA-N 0.000 description 2
- UNSASAAIXDIMQQ-FGZHOGPDSA-N [4-(2-octoxypyrimidin-5-yl)phenyl] (2r,3r)-3-propyloxirane-2-carboxylate Chemical compound C1=NC(OCCCCCCCC)=NC=C1C(C=C1)=CC=C1OC(=O)[C@H]1[C@@H](CCC)O1 UNSASAAIXDIMQQ-FGZHOGPDSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical class C1COCO1 WNXJIVFYUVYPPR-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
- 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 1
- NSGXVIFQFGUIKP-ZCYQVOJMSA-N 2-[4-[(2s,3s)-3-butyl-2-methyloxiran-2-yl]phenyl]-5-octylpyrimidine Chemical compound N1=CC(CCCCCCCC)=CN=C1C1=CC=C([C@@]2(C)[C@@H](O2)CCCC)C=C1 NSGXVIFQFGUIKP-ZCYQVOJMSA-N 0.000 description 1
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical class C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 1
- QYSPVZCWUWZCPV-UHFFFAOYSA-N 5-butoxy-2-(4-pentoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCC)=CC=C1C1=NC=C(OCCCC)C=N1 QYSPVZCWUWZCPV-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- MZOYMQRKTJRHGJ-UHFFFAOYSA-N THTC Chemical compound OC(=O)C1CCCS1 MZOYMQRKTJRHGJ-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
Classifications
-
- 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
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/46—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing esters
-
- 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
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/58—Dopants or charge transfer agents
-
- 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
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/58—Dopants or charge transfer agents
- C09K19/586—Optically active dopants; chiral dopants
- C09K19/588—Heterocyclic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Liquid Crystal Substances (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3909355A DE3909355A1 (de) | 1989-03-22 | 1989-03-22 | Ferroelektrische fluessigkristalline mischungen |
| TW079102049A TW208067B (OSRAM) | 1989-03-22 | 1990-03-15 | |
| CA002049960A CA2049960A1 (en) | 1989-03-22 | 1990-03-21 | Ferroelectric liquid crystal mixtures |
| JP2504661A JPH04504272A (ja) | 1989-03-22 | 1990-03-21 | 強誘電性液晶混合物 |
| DE59009244T DE59009244D1 (de) | 1989-03-22 | 1990-03-21 | Ferroelektrische flüssigkristalline mischungen. |
| PCT/EP1990/000457 WO1990011335A1 (de) | 1989-03-22 | 1990-03-21 | Ferroelektrische flüssigkristalline mischungen |
| EP90904624A EP0464058B1 (de) | 1989-03-22 | 1990-03-21 | Ferroelektrische flüssigkristalline mischungen |
| US07/761,813 US5378394A (en) | 1989-03-22 | 1990-03-21 | Ferroelectric liquid-crystalline mixtures |
| KR1019910701142A KR920701394A (ko) | 1989-03-22 | 1991-09-18 | 강유전성 액정 혼합물 |
| NO91913697A NO913697L (no) | 1989-03-22 | 1991-09-19 | Ferroelektriske flytende krystallblandinger. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3909355A DE3909355A1 (de) | 1989-03-22 | 1989-03-22 | Ferroelektrische fluessigkristalline mischungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3909355A1 true DE3909355A1 (de) | 1990-09-27 |
Family
ID=6376915
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3909355A Withdrawn DE3909355A1 (de) | 1989-03-22 | 1989-03-22 | Ferroelektrische fluessigkristalline mischungen |
| DE59009244T Expired - Fee Related DE59009244D1 (de) | 1989-03-22 | 1990-03-21 | Ferroelektrische flüssigkristalline mischungen. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59009244T Expired - Fee Related DE59009244D1 (de) | 1989-03-22 | 1990-03-21 | Ferroelektrische flüssigkristalline mischungen. |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5378394A (OSRAM) |
| EP (1) | EP0464058B1 (OSRAM) |
| JP (1) | JPH04504272A (OSRAM) |
| CA (1) | CA2049960A1 (OSRAM) |
| DE (2) | DE3909355A1 (OSRAM) |
| TW (1) | TW208067B (OSRAM) |
| WO (1) | WO1990011335A1 (OSRAM) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4143139A1 (de) * | 1991-12-28 | 1993-07-01 | Hoechst Ag | Chirale oxiranylmethyl-ether und ihre verwendung als dotierstoffe in fluessigkristallmischungen |
| US7195719B1 (en) | 2001-01-03 | 2007-03-27 | Displaytech, Inc. | High polarization ferroelectric liquid crystal compositions |
| US6838128B1 (en) | 2002-02-05 | 2005-01-04 | Displaytech, Inc. | High polarization dopants for ferroelectric liquid crystal compositions |
| CN113867063B (zh) * | 2021-10-28 | 2022-12-16 | 华南理工大学 | 一种铁电螺旋液晶材料及其实现二次谐波增强的方法 |
| CN118005574A (zh) * | 2023-12-28 | 2024-05-10 | 深圳市宝安区新材料研究院 | 一种手性发光分子及其制备方法、手性发光液晶 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3633968A1 (de) * | 1986-10-06 | 1988-04-07 | Hoechst Ag | Chirale aryl-2,3-epoxyalkyl-ether und deren entsprechende thioverbindungen und ihre verwendung als dotierstoff in fluessigkristall-phasen |
| JPS63179835A (ja) * | 1986-12-20 | 1988-07-23 | メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | シクロペンタン誘導体 |
| DE3831226A1 (de) * | 1987-09-19 | 1989-03-30 | Hoechst Ag | Fluessigkristalline, insbesondere ferroelektrische fluessigkristalline mischungen |
| DE3824902A1 (de) * | 1988-07-22 | 1990-02-15 | Hoechst Ag | Optisch aktive, in 4-stellung einen mesogenen rest tragende 1,3-dioxolan-derivate, ein verfahren zu ihrer herstellung und ihre verwendung als dotierstoffe in fluessigkristallmischungen |
| DE3827599A1 (de) * | 1988-08-13 | 1990-02-15 | Hoechst Ag | Verwendung von optisch aktiven tetrahydrofuran-2-carbonsaeureestern als dotierstoffe in fluessigkristallmischungen, diese enthaltende fluessigkristallmischungen und neue optisch aktive tetrahydrofuran-2-carbonsaeureester |
-
1989
- 1989-03-22 DE DE3909355A patent/DE3909355A1/de not_active Withdrawn
-
1990
- 1990-03-15 TW TW079102049A patent/TW208067B/zh active
- 1990-03-21 WO PCT/EP1990/000457 patent/WO1990011335A1/de not_active Ceased
- 1990-03-21 US US07/761,813 patent/US5378394A/en not_active Expired - Lifetime
- 1990-03-21 CA CA002049960A patent/CA2049960A1/en not_active Abandoned
- 1990-03-21 DE DE59009244T patent/DE59009244D1/de not_active Expired - Fee Related
- 1990-03-21 JP JP2504661A patent/JPH04504272A/ja active Pending
- 1990-03-21 EP EP90904624A patent/EP0464058B1/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0464058B1 (de) | 1995-06-14 |
| TW208067B (OSRAM) | 1993-06-21 |
| JPH04504272A (ja) | 1992-07-30 |
| DE59009244D1 (de) | 1995-07-20 |
| EP0464058A1 (de) | 1992-01-08 |
| US5378394A (en) | 1995-01-03 |
| CA2049960A1 (en) | 1990-09-23 |
| WO1990011335A1 (de) | 1990-10-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |