CA2049960A1 - Ferroelectric liquid crystal mixtures - Google Patents
Ferroelectric liquid crystal mixturesInfo
- Publication number
- CA2049960A1 CA2049960A1 CA002049960A CA2049960A CA2049960A1 CA 2049960 A1 CA2049960 A1 CA 2049960A1 CA 002049960 A CA002049960 A CA 002049960A CA 2049960 A CA2049960 A CA 2049960A CA 2049960 A1 CA2049960 A1 CA 2049960A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- optically active
- mixture
- integer
- mol
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 110
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 title claims description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 150000002148 esters Chemical class 0.000 claims abstract description 9
- JRFVJVVAMLTIAP-UHFFFAOYSA-N 4-(1,3-dioxolan-4-yloxy)-1,3-dioxolane Chemical class O1COCC1OC1OCOC1 JRFVJVVAMLTIAP-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- -1 pyrimidine-2,5-diyl Chemical group 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 150000002170 ethers Chemical class 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 4
- 150000007942 carboxylates Chemical class 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000003230 pyrimidines Chemical class 0.000 claims description 3
- HAIBGXNWAUQCEG-UHFFFAOYSA-N 1,3-dioxolane-4-carboxylic acid Chemical class OC(=O)C1COCO1 HAIBGXNWAUQCEG-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- OTGHWLKHGCENJV-UHFFFAOYSA-N glycidic acid Chemical class OC(=O)C1CO1 OTGHWLKHGCENJV-UHFFFAOYSA-N 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 2
- MZOYMQRKTJRHGJ-UHFFFAOYSA-N THTC Chemical compound OC(=O)C1CCCS1 MZOYMQRKTJRHGJ-UHFFFAOYSA-N 0.000 claims 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical class OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims 1
- 150000004862 dioxolanes Chemical group 0.000 claims 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 claims 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims 1
- 230000010287 polarization Effects 0.000 abstract description 20
- 230000002269 spontaneous effect Effects 0.000 abstract description 13
- 239000007788 liquid Substances 0.000 abstract description 5
- UJJLJRQIPMGXEZ-UHFFFAOYSA-N tetrahydro-2-furoic acid Chemical compound OC(=O)C1CCCO1 UJJLJRQIPMGXEZ-UHFFFAOYSA-N 0.000 abstract description 3
- 238000002844 melting Methods 0.000 description 17
- 230000008018 melting Effects 0.000 description 17
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 12
- 150000002500 ions Chemical class 0.000 description 12
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- CBQYNPHHHJTCJS-UHFFFAOYSA-N Alline Chemical compound C1=CC=C2C3(O)CCN(C)C3NC2=C1 CBQYNPHHHJTCJS-UHFFFAOYSA-N 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- JWEQRJSCTFBRSI-PCLIKHOPSA-N rboxylate Chemical compound COC(=O)C1C(N2C3=O)C4=CC=CC=C4OC1(C)N=C2S\C3=C\C(C=1)=CC=C(OC)C=1COC1=CC=CC=C1C JWEQRJSCTFBRSI-PCLIKHOPSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- OZPFVBLDYBXHAF-UHFFFAOYSA-M 2,2-dimethyl-1,3-dioxolane-4-carboxylate Chemical compound CC1(C)OCC(C([O-])=O)O1 OZPFVBLDYBXHAF-UHFFFAOYSA-M 0.000 description 1
- 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 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
- 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 1
- SYURNNNQIFDVCA-UHFFFAOYSA-N 2-propyloxirane Chemical compound CCCC1CO1 SYURNNNQIFDVCA-UHFFFAOYSA-N 0.000 description 1
- 101150034533 ATIC gene Proteins 0.000 description 1
- 102100036364 Cadherin-2 Human genes 0.000 description 1
- 240000007681 Catha edulis Species 0.000 description 1
- 235000006696 Catha edulis Nutrition 0.000 description 1
- 102100022404 E3 ubiquitin-protein ligase Midline-1 Human genes 0.000 description 1
- 101710102210 E3 ubiquitin-protein ligase Midline-1 Proteins 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 244000228957 Ferula foetida Species 0.000 description 1
- 101000714537 Homo sapiens Cadherin-2 Proteins 0.000 description 1
- 101000994460 Homo sapiens Keratin, type I cytoskeletal 20 Proteins 0.000 description 1
- 102100032700 Keratin, type I cytoskeletal 20 Human genes 0.000 description 1
- 241000353097 Molva molva Species 0.000 description 1
- 101100400378 Mus musculus Marveld2 gene Proteins 0.000 description 1
- 101150071542 NAA30 gene Proteins 0.000 description 1
- HCBIBCJNVBAKAB-UHFFFAOYSA-N Procaine hydrochloride Chemical compound Cl.CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 HCBIBCJNVBAKAB-UHFFFAOYSA-N 0.000 description 1
- 102100039233 Pyrin Human genes 0.000 description 1
- 108010059278 Pyrin Proteins 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- YFNONBGXNFCTMM-UHFFFAOYSA-N butoxybenzene Chemical group CCCCOC1=CC=CC=C1 YFNONBGXNFCTMM-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- GXHVDDBBWDCOTF-UHFFFAOYSA-N ever-1 Natural products CCC(C)C(=O)OC1C(CC(C)C23OC(C)(C)C(CC(OC(=O)c4cccnc4)C12COC(=O)C)C3OC(=O)C)OC(=O)C GXHVDDBBWDCOTF-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000000819 phase cycle Methods 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 101150011748 pyrL gene Proteins 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 230000002195 synergetic effect Effects 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3909355.7 | 1989-03-22 | ||
| DE3909355A DE3909355A1 (de) | 1989-03-22 | 1989-03-22 | Ferroelektrische fluessigkristalline mischungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2049960A1 true CA2049960A1 (en) | 1990-09-23 |
Family
ID=6376915
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002049960A Abandoned CA2049960A1 (en) | 1989-03-22 | 1990-03-21 | Ferroelectric liquid crystal mixtures |
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 |
| DE3909355A1 (de) | 1990-09-27 |
| WO1990011335A1 (de) | 1990-10-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |