JP4201855B2 - ベンゼン誘導体および液晶媒体 - Google Patents

ベンゼン誘導体および液晶媒体 Download PDF

Info

Publication number: JP4201855B2
Authority: JP; Japan
Prior art keywords: liquid crystal; formula; crystal medium; group; medium according
Prior art date: 1995-10-10
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 - Lifetime

Application number

JP28586796A

Other languages

English (en)

Japanese (ja)

Other versions

JPH09125066A (ja

JPH09125066A5 (2

Inventor

ヒロシ・ヌマタ

ヒデオ・イチノセ

フミオ・シマノ

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Merck Patent GmbH

Original Assignee

Merck Patent GmbH

Priority date (The priority date 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 date listed.)

1995-10-10

Filing date

1996-10-09

Publication date

2008-12-24

1996-10-09 Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH

1997-05-13 Publication of JPH09125066A publication Critical patent/JPH09125066A/ja

2004-10-14 Publication of JPH09125066A5 publication Critical patent/JPH09125066A5/ja

2008-12-24 Application granted granted Critical

2008-12-24 Publication of JP4201855B2 publication Critical patent/JP4201855B2/ja

2016-10-09 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000004973 liquid crystal related substance Substances 0.000 title claims description 57
125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 81
239000000203 mixture Substances 0.000 claims description 31
125000004432 carbon atom Chemical group C* 0.000 claims description 24
125000000217 alkyl group Chemical group 0.000 claims description 23
125000003342 alkenyl group Chemical group 0.000 claims description 16
229910052731 fluorine Inorganic materials 0.000 claims description 15
229910052740 iodine Inorganic materials 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 8
125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 7
125000005407 trans-1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])[C@]([H])([*:2])C([H])([H])C([H])([H])[C@@]1([H])[*:1] 0.000 claims description 7
239000011737 fluorine Chemical group 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000003709 fluoroalkyl group Chemical group 0.000 claims description 4
125000005725 cyclohexenylene group Chemical group 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000005449 2-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C([H])=C(F)C([*:1])=C1[H] 0.000 claims description 2
125000005451 3-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:1])C([H])=C(F)C([*:2])=C1[H] 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
-1 ethoxy, propoxy, butoxy, pentoxy, hexoxy Chemical group 0.000 description 84
239000000463 material Substances 0.000 description 11
239000000758 substrate Substances 0.000 description 10
239000011159 matrix material Substances 0.000 description 9
230000000694 effects Effects 0.000 description 7
230000003287 optical effect Effects 0.000 description 7
239000000460 chlorine Substances 0.000 description 6
0 *c(cc1)ccc1*(c(cc1)cc(F)c1C#N)=O Chemical compound *c(cc1)ccc1*(c(cc1)cc(F)c1C#N)=O 0.000 description 5
239000004990 Smectic liquid crystal Substances 0.000 description 5
230000005540 biological transmission Effects 0.000 description 5
239000000126 substance Substances 0.000 description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
230000007423 decrease Effects 0.000 description 3
230000002349 favourable effect Effects 0.000 description 3
239000011521 glass Substances 0.000 description 3
238000000034 method Methods 0.000 description 3
238000002156 mixing Methods 0.000 description 3
230000005855 radiation Effects 0.000 description 3
230000007704 transition Effects 0.000 description 3
OXBRRUNAAVNTOZ-UHFFFAOYSA-N 1-ethoxy-4-(4-propylcyclohexyl)benzene Chemical compound C1CC(CCC)CCC1C1=CC=C(OCC)C=C1 OXBRRUNAAVNTOZ-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
239000002019 doping agent Substances 0.000 description 2
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
229910021420 polycrystalline silicon Inorganic materials 0.000 description 2
125000004742 propyloxycarbonyl group Chemical group 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000004065 semiconductor Substances 0.000 description 2
239000010409 thin film Substances 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 description 1
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
125000005916 2-methylpentyl group Chemical group 0.000 description 1
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
125000005917 3-methylpentyl group Chemical group 0.000 description 1
125000006043 5-hexenyl group Chemical group 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
229920000106 Liquid crystal polymer Polymers 0.000 description 1
239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 description 1
239000004988 Nematic liquid crystal Substances 0.000 description 1
241000050617 Papilio paris Species 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
241000620457 Telestes souffia Species 0.000 description 1
206010047571 Visual impairment Diseases 0.000 description 1
239000000654 additive Substances 0.000 description 1
229910021417 amorphous silicon Inorganic materials 0.000 description 1
238000005452 bending Methods 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
UHYPYGJEEGLRJD-UHFFFAOYSA-N cadmium(2+);selenium(2-) Chemical compound [Se-2].[Cd+2] UHYPYGJEEGLRJD-UHFFFAOYSA-N 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
230000003098 cholesteric effect Effects 0.000 description 1
238000004883 computer application Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000010276 construction Methods 0.000 description 1
229920001577 copolymer Chemical group 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000003989 dielectric material Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000005684 electric field Effects 0.000 description 1
230000005670 electromagnetic radiation Effects 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
230000009931 harmful effect Effects 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
229910021421 monocrystalline silicon Inorganic materials 0.000 description 1
125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- 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
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- 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
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3021—Cy-Ph-Ph-Cy

Landscapes

Chemical & Material Sciences (AREA)
Crystallography & Structural Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Organic Chemistry (AREA)
Liquid Crystal Substances (AREA)

JP28586796A 1995-10-10 1996-10-09 ベンゼン誘導体および液晶媒体 Expired - Lifetime JP4201855B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP95115939		1995-10-10
DE95115939.1		1995-10-10

Publications (3)

Publication Number	Publication Date
JPH09125066A JPH09125066A (ja)	1997-05-13
JPH09125066A5 JPH09125066A5 (2)	2004-10-14
JP4201855B2 true JP4201855B2 (ja)	2008-12-24

Family

ID=8219705

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP28586796A Expired - Lifetime JP4201855B2 (ja)	1995-10-10	1996-10-09	ベンゼン誘導体および液晶媒体

Country Status (2)

Country	Link
US (1)	US5827450A (2)
JP (1)	JP4201855B2 (2)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TW305872B (2)	1995-06-08	1997-05-21	Chisso Corp
EP0842238B1 (de) *	1995-08-01	2001-11-21	MERCK PATENT GmbH	Flüssigkristallines medium
AU5678998A (en) *	1997-01-29	1998-08-18	Chisso Corporation	Liquid-crystal compounds having fluorinated alkyl groups, liquid-crystal composition, and liquid-crystal display element
US6929832B2 (en) *	1999-03-03	2005-08-16	Merck Patent Gmbh	Liquid-crystal medium, and electro-optical display containing the liquid-crystal medium
DE19961702B4 (de) *	1999-12-21	2010-09-30	Merck Patent Gmbh	Flüssigkristallines Medium und seine Verwendung
TW588106B (en) *	2000-04-17	2004-05-21	Merck Patent Gmbh	Liquid-crystalline medium having a low threshold voltage
DE10125708A1 (de) *	2000-06-21	2002-03-28	Merck Kgaa	Hochohmige nematische flüssigkristalline Mischungen und Reinigngsverfahren dafür
DE10150198A1 (de) *	2001-10-12	2003-04-24	Merck Patent Gmbh	Flüssigkristallines Medium

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5970624A (ja) *	1982-10-13	1984-04-21	Chisso Corp	トランス，トランス−４−アルキル−４′−アルキルビシクロヘキサン類
DE3321373A1 (de) *	1983-06-14	1984-12-20	Merck Patent Gmbh, 6100 Darmstadt	Bicyclohexyle
DE3909802A1 (de) *	1988-07-27	1990-04-05	Merck Patent Gmbh	Difluormethylverbindungen
US5324449A (en) *	1987-09-25	1994-06-28	Merck Patent Gesellschaft Mit Beschrankter Haftung	Substituted phenyl trifluoromethyl ethers
US5536442A (en) *	1987-09-25	1996-07-16	Merck Patent Gesellschaft Mit Beschrankter Haftung	Fluorinated liquid crystal compounds and liquid crystal medium containing same
DK0441932T3 (da) *	1989-09-06	1995-04-03	Merck Patent Gmbh	Flourbenzenderivater og flydendekrystallinsk medium
KR0171590B1 (ko) *	1990-04-13	1999-03-20	위르겐 호이만, 라인하르트 슈틀러	액정 매질
EP0477329B1 (de) *	1990-04-13	1996-03-20	MERCK PATENT GmbH	Flüssigkristallines medium
DE69125055T2 (de) *	1990-06-08	1997-09-11	Merck Patent Gmbh	Supertwist Flüssigkristallanzeige
DE4107119A1 (de) *	1990-08-03	1992-02-06	Merck Patent Gmbh	Fluessigkristallines medium
US5409637A (en) *	1991-02-20	1995-04-25	Merck Patent Gesellschaft Mit Beschrankter Haftung	Nematic liquid-crystal composition
DE4119999A1 (de) *	1991-04-12	1992-10-15	Merck Patent Gmbh	Supertwist-fluessigkristallanzeige
JPH06108053A (ja) *	1992-09-30	1994-04-19	Dainippon Ink & Chem Inc	ネマチック液晶組成物及びこれを用いた液晶表示装置
JP3554577B2 (ja) *	1993-02-03	2004-08-18	メルクパテントゲゼルシャフトミットベシュレンクテルハフトング	液晶媒体
JP3453781B2 (ja) *	1993-03-25	2003-10-06	大日本インキ化学工業株式会社	ネマチック液晶組成物及びこれを用いた液晶表示装置
US5422035A (en) *	1993-05-10	1995-06-06	Merck Patent Gesellschaft Mit Beschrankter Haftung	Benzene derivatives, and liquid-crystalline medium
DE4338164A1 (de) *	1993-11-09	1995-05-11	Merck Patent Gmbh	Verfahren zur Herstellung von substituiertem 2,2-Difluorethoxybenzol
DE4428766B4 (de) *	1993-08-28	2013-11-28	Merck Patent Gmbh	Benzolderivate und flüssigkristallines Medium
JP3584486B2 (ja) *	1994-03-08	2004-11-04	大日本インキ化学工業株式会社	ネマチック液晶組成物及びこれを用いた液晶表示装置

1996
- 1996-10-09 US US08/728,376 patent/US5827450A/en not_active Expired - Lifetime
- 1996-10-09 JP JP28586796A patent/JP4201855B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
JPH09125066A (ja)	1997-05-13
US5827450A (en)	1998-10-27

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