KR100271086B1 - Liquid crystal compounds having perfluoroether terminal portions - Google Patents

Liquid crystal compounds having perfluoroether terminal portions Download PDF

Info

Publication number: KR100271086B1
Authority: KR; South Korea
Prior art keywords: liquid crystal; terminal portions; crystal compounds; perfluoroether terminal; perfluoroether
Prior art date: 1992-04-28
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

Application number

KR1019940703830A

Other languages

English (en)

Other versions

KR950701375A (ko

Inventor

Eugene P Janulis

Gilbert C Johnson

Patricia M Savu

Terence D Spawn

Original Assignee

Minnesota Mining & Mfg

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.)

1992-04-28

Filing date

1994-10-27

Publication date

2000-11-01

1994-10-27 Application filed by Minnesota Mining & Mfg filed Critical Minnesota Mining & Mfg

1995-03-23 Publication of KR950701375A publication Critical patent/KR950701375A/ko

2000-11-01 Application granted granted Critical

2000-11-01 Publication of KR100271086B1 publication Critical patent/KR100271086B1/ko

2014-10-27 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/55—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and esterified hydroxy groups bound to the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/12—Saturated ethers containing halogen
- C07C43/123—Saturated ethers containing halogen both carbon chains are substituted by halogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/12—Saturated ethers containing halogen
- C07C43/126—Saturated ethers containing halogen having more than one ether bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/13—Saturated ethers containing hydroxy or O-metal groups
- C07C43/137—Saturated ethers containing hydroxy or O-metal groups containing halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
- C07C43/1786—Unsaturated ethers containing hydroxy or O-metal groups containing halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
- 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
- C07D239/26—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- 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
- C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
- 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
- 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
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
- 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
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
- 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
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- 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
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
- 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
- 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
- C09K19/3444—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 one nitrogen atom, e.g. pyridine
- 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*-
- 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
- C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero 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
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
- C09K2019/325—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring containing a tetrahydronaphthalene, e.g. -2,6-diyl (tetralin)

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Crystallography & Structural Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Liquid Crystal Substances (AREA)
Pyridine Compounds (AREA)

KR1019940703830A 1992-04-28 1994-10-27 Liquid crystal compounds having perfluoroether terminal portions Expired - Fee Related KR100271086B1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US07/875,223 US5262082A (en)	1992-04-28	1992-04-28	Ferroelectric liquid crystal compounds having perfluoroether terminal portions
US08/045,283 US5437812A (en)	1992-04-28	1993-04-16	Liquid crystal compounds having perfluoroether terminal portions
PCT/US1993/003925 WO1993022396A1 (en)	1992-04-28	1993-04-26	Liquid crystal compounds having perfluoroether terminal portions

Publications (2)

Publication Number	Publication Date
KR950701375A KR950701375A (ko)	1995-03-23
KR100271086B1 true KR100271086B1 (en)	2000-11-01

Family

ID=25365401

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
KR1019940703830A Expired - Fee Related KR100271086B1 (en)	1992-04-28	1994-10-27	Liquid crystal compounds having perfluoroether terminal portions

Country Status (11)

Country	Link
US (2)	US5262082A (ko)
EP (1)	EP0638112B1 (ko)
JP (1)	JP3515109B2 (ko)
KR (1)	KR100271086B1 (ko)
CA (1)	CA2133652A1 (ko)
DE (1)	DE69332190T2 (ko)
FI (1)	FI945069A0 (ko)
MX (1)	MX9302467A (ko)
MY (1)	MY108861A (ko)
TW (1)	TW253906B (ko)
WO (1)	WO1993022396A1 (ko)

Families Citing this family (71)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5585036A (en) *	1988-03-04	1996-12-17	Displaytech, Inc.	Liquid crystal compounds containing chiral 2-halo-2-methyl ether and ester tails
DE59209827D1 (de) *	1991-02-12	2000-05-25	Merck Patent Gmbh	Flüssigkristalline verbindungen
US5482650A (en) *	1992-04-28	1996-01-09	Minnesota Mining And Manufacturing Company	Liquid crystal compounds having perfluoroether terminal portions
US5262082A (en) *	1992-04-28	1993-11-16	Minnesota Mining And Manufacturing Company	Ferroelectric liquid crystal compounds having perfluoroether terminal portions
US5458806A (en) *	1993-01-22	1995-10-17	Merck Patent Gesellschaft Mit Beschrankter Haftung	Fluoromethyl ketones and liquid-crystalline media
CA2121776C (en) *	1993-04-28	1999-05-25	Yasuto Kodera	Liquid crystal device with a liquid crystal in an optical modulation region having a pretilt angle smaller than the liquid crystal in a peripheral region surrounding the optical modulation region
DE4416272C2 (de) *	1993-05-19	2003-09-11	Merck Patent Gmbh	Partiell fluorierte Benzolderivate
EP0640676B1 (en) *	1993-08-31	1999-01-20	Canon Kabushiki Kaisha	Mesomorphic compound, liquid crystal composition containing the compound, liquid crystal device using the composition, liquid crystal apparatus and display method
EP0641850B1 (en) *	1993-09-06	2000-04-26	Canon Kabushiki Kaisha	Mesomorphic compound, liquid crystal composition containing the compound, liquid crystal device using the composition, liquid crystal apparatus and display method
US5399291A (en) *	1993-09-30	1995-03-21	Minnesota Mining And Manufacturing Company	Liquid crystal compounds having a fluoroether terminal portion
US5474705A (en) *	1993-12-22	1995-12-12	Minnesota Mining And Manufacturing Company	Chiral liquid crystal compounds having a perfluoroether terminal portion
US5417883A (en) *	1994-04-11	1995-05-23	Minnesota Mining And Manufacturing Company	Process for controlling layer spacing in mixtures of smectic liquid crystal compounds
EP0677565B1 (en) *	1994-04-14	2000-10-18	Canon Kabushiki Kaisha	Liquid crystal composition, liquid crystal device using the composition, liquid crystal apparatus and display method
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JP3227338B2 (ja)	1994-04-14	2001-11-12	キヤノン株式会社	液晶組成物、これを用いた液晶素子、液晶装置、及び表示方法
US5943035A (en) *	1994-04-20	1999-08-24	Canon Kabushiki Kaisha	Driving method and apparatus for liquid crystal device
EP0683417A1 (en) *	1994-05-17	1995-11-22	Canon Kabushiki Kaisha	Liquid crystal device and liquid crystal apparatus
US5658962A (en) *	1994-05-20	1997-08-19	Minnesota Mining And Manufacturing Company	Omega-hydrofluoroalkyl ethers, precursor carboxylic acids and derivatives thereof, and their preparation and application
US5476974A (en) *	1994-05-20	1995-12-19	Minnesota Mining And Manufacturing Company	Omega-hydrofluoroalkyl ethers, precursor carboxylic acids and derivatives thereof, and their preparation and application
EP0694599B1 (en) *	1994-07-26	2001-06-27	Canon Kabushiki Kaisha	Liquid crystal composition, liquid crystal device using the composition, liquid crystal apparatus and display method
DE69526291D1 (de) *	1994-08-04	2002-05-16	Canon Kk	Flüssigkristallvorrichtung
EP0703561A3 (en)	1994-09-26	1996-12-18	Canon Kk	Method and device for controlling a display device
US5808594A (en) *	1994-09-26	1998-09-15	Canon Kabushiki Kaisha	Driving method for display device and display apparatus
US5798056A (en) *	1995-02-01	1998-08-25	Canon Kabushiki Kaisha	Aligning method of liquid crystal, production process of liquid crystal device, and liquid crystal device
US5702637A (en) *	1995-04-19	1997-12-30	Minnesota Mining And Manufacturing Company	Liquid crystal compounds having a chiral fluorinated terminal portion
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US5861108A (en) *	1995-07-07	1999-01-19	Mitsui Chemicals, Inc.	Naphthalene compound, and liquid crystal composition and liquid crystal element using the same
US5858273A (en) *	1995-07-27	1999-01-12	Canon Kabushiki Kaisha	Liquid crystal device
US5841497A (en) *	1995-07-28	1998-11-24	Canon Kabushiki Kaisha	Liquid crystal device and liquid crystal apparatus
JP3160701B2 (ja)	1995-07-28	2001-04-25	キヤノン株式会社	液晶素子及び液晶装置
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US5858269A (en) *	1995-09-20	1999-01-12	Canon Kabushiki Kaisha	Liquid crystal device and liquid crystal apparatus
US5933213A (en) *	1995-09-26	1999-08-03	Imation Corp.	Apparatus and method for imparting a succession of predetermined latent images on a strip of unexposed light sensitive film
US5658491A (en) *	1995-10-12	1997-08-19	Minnesota Mining And Manufacturing Company	Process for controlling cone tilt angle in mixtures of smectic liquid crystal compounds
US6177152B1 (en)	1995-10-20	2001-01-23	Canon Kabushiki Kaisha	Liquid crystal device and liquid crystal apparatus
US5932136A (en) *	1995-10-20	1999-08-03	Canon Kabushiki Kaisha	Liquid crystal device and liquid crystal apparatus
JPH09146126A (ja) *	1995-11-22	1997-06-06	Canon Inc	液晶装置及び情報伝達装置
US5999157A (en) *	1995-12-27	1999-12-07	Canon Kabushiki Kaisha	Suppressing liquid crystal movement based on the relationship between a display pattern and a driving waveform
US5835181A (en) *	1995-12-27	1998-11-10	Canon Kabushiki Kaisha	Process for producing liquid crystal including discharging liquid crystal material through second aperture
US5885482A (en) *	1995-12-28	1999-03-23	Canon Kabushiki Kaisha	Liquid crystal device, production process thereof and liquid crystal apparatus
JP3093627B2 (ja)	1996-02-09	2000-10-03	キヤノン株式会社	液晶表示装置の製造方法
JPH1068923A (ja) *	1996-06-17	1998-03-10	Canon Inc	液晶素子及びそれを用いた液晶装置
US6154265A (en) *	1996-06-18	2000-11-28	Canon Kabushiki Kaisha	Liquid crystal device and production process thereof
JP3192593B2 (ja) *	1996-07-22	2001-07-30	キヤノン株式会社	液晶素子
US5973761A (en) *	1997-01-31	1999-10-26	Canon Kabushiki Kaisha	Ferroelectic liquid crystal device having a low-resistivity layer below an alignment control layer
US5855812A (en) *	1997-04-11	1999-01-05	Minnesota Mining And Manufacturing Company	Compounds and process for controlling cone tilt angle in mixtures of smectic liquid crystal compounds
JPH11100577A (ja) *	1997-07-31	1999-04-13	Canon Inc	液晶の配向方法、液晶素子の製造方法、該製造方法により得られる液晶素子、液晶装置
US6195147B1 (en)	1997-08-01	2001-02-27	Canon Kabushiki Kaisha	Liquid crystal substrate with optical modulation region having different alignment control forces
US6139927A (en) *	1997-09-18	2000-10-31	Canon Kabushiki Kaisha	Liquid crystal device
EP0916715A1 (en) *	1997-11-11	1999-05-19	Aventis Research & Technologies GmbH & Co. KG	Chiral smectic liquid crystal mixture containing compounds with fluorinated sidechains
US6309561B1 (en)	1997-12-24	2001-10-30	3M Innovative Properties Company	Liquid crystal compounds having a chiral fluorinated terminal portion
US6057007A (en) *	1998-08-10	2000-05-02	3M Innovative Properties Company	Tristable liquid crystal display device
US6084649A (en) *	1998-08-10	2000-07-04	3M Innovative Properties Company	Tristable liquid crystal display device
US6139924A (en) *	1998-11-20	2000-10-31	3M Innovative Properties Company	Chiral liquid crystal compounds having a fluorinated terminal portion
US6417828B1 (en)	1999-02-18	2002-07-09	Canon Kabushiki Kaisha	Liquid crystal composition, liquid crystal device, driving method thereof and liquid crystal apparatus
US6221543B1 (en) *	1999-05-14	2001-04-24	3M Innovatives Properties	Process for making active substrates for color displays
US6870163B1 (en)	1999-09-01	2005-03-22	Displaytech, Inc.	Ferroelectric liquid crystal devices using materials with a de Vries smectic A phase
US7083832B2 (en)	2000-09-01	2006-08-01	Displaytech, Inc.	Partially fluorinated liquid crystal material
US7195719B1 (en)	2001-01-03	2007-03-27	Displaytech, Inc.	High polarization ferroelectric liquid crystal compositions
US6703082B1 (en)	2001-06-20	2004-03-09	Displaytech, Inc.	Bookshelf liquid crystal materials and devices
US6838128B1 (en)	2002-02-05	2005-01-04	Displaytech, Inc.	High polarization dopants for ferroelectric liquid crystal compositions
US6841079B2 (en) *	2002-05-31	2005-01-11	3M Innovative Properties Company	Fluorochemical treatment for silicon articles
US7744943B2 (en) *	2003-05-12	2010-06-29	Grand Brands, LLC	Edible mix and method of making the same
WO2011065312A1 (ja) *	2009-11-26	2011-06-03	旭硝子株式会社	エーテル化合物、これを含む潤滑剤および潤滑剤用組成物
US20120255651A1 (en) *	2011-04-07	2012-10-11	E.I. Du Pont De Nemours And Company	Fluoroalkylalkoxylates
US20120259143A1 (en) *	2011-04-07	2012-10-11	E.I. Du Pont De Nemours And Company	Fluoroalkylalkoxylates
WO2013031603A1 (ja) *	2011-08-29	2013-03-07	Ａｇｃセイミケミカル株式会社	液晶化合物およびその製造方法、液晶組成物および液晶電気光学素子
CN102898287B (zh) *	2012-09-28	2016-03-30	江苏和成显示科技股份有限公司	新型二氟代乙二醚类液晶及其组合物
JP6718657B2 (ja)	2015-02-27	2020-07-08	住友化学株式会社	組成物
KR102676388B1 (ko)	2015-07-24	2024-06-18	스미또모 가가꾸 가부시끼가이샤	조성물, 조성물을 함유하는 광학 필름, 광학 필름의 제조 방법
DE102017010942A1 (de) *	2016-12-08	2018-06-14	Merck Patent Gmbh	Additive für Flüssigkristallmischungen

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1991000897A1 (de) *	1989-07-11	1991-01-24	MERCK Patent Gesellschaft mit beschränkter Haftung	Chirale oder achirale ringverbindungen

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1601601A (en) *	1978-01-18	1981-11-04	Standard Telephones Cables Ltd	Liquid crystal display cells
US4367924A (en) *	1980-01-08	1983-01-11	Clark Noel A	Chiral smectic C or H liquid crystal electro-optical device
GB2067811B (en) *	1980-01-16	1983-08-10	Standard Telephones Cables Ltd	Co-ordinate addressing of smetic display cells
JPS62129251A (ja) *	1985-12-02	1987-06-11	Nippon Kayaku Co Ltd	トランス−４−アルキルシクロヘキサン−１−カルボン酸エステル類
CA1341138C (en) *	1986-06-30	2000-11-14	Minnesota Mining And Manufacturing Company	Fluorine-containing chiral smectic liquid crystals
US4886619A (en) *	1986-06-30	1989-12-12	Minnesota Mining And Manufacturing Company	Fluorine-containing chiral smectic liquid crystals
US5132041A (en) *	1986-07-21	1992-07-21	Polaroid Corporation	Liquid crystal compounds having ether tail moiety
DE3714043A1 (de) *	1987-04-28	1988-11-17	Merck Patent Gmbh	Elektrooptisches fluessigkristallanzeigeelement
DE3909802A1 (de) *	1988-07-27	1990-04-05	Merck Patent Gmbh	Difluormethylverbindungen
DE68911171T2 (de) *	1988-02-29	1994-04-07	Showa Shell Sekiyu	Flüssigkristall-Verbindungen mit Fluoroalkylradikalen.
DE3825424A1 (de) *	1988-07-27	1990-03-29	Merck Patent Gmbh	Fluorierte alkoxyverbindungen
US5082587A (en) *	1988-09-23	1992-01-21	Janulis Eugene P	Achiral fluorine-containing liquid crystals
JP2768365B2 (ja) *	1989-06-24	1998-06-25	富士通株式会社	液晶組成物
JPH0393748A (ja) *	1989-09-04	1991-04-18	Nippon Telegr & Teleph Corp <Ntt>	光学活性化合物および液晶組成物
JPH03221588A (ja) *	1990-01-26	1991-09-30	Showa Shell Sekiyu Kk	液晶組成物用配合剤およびそれらを含む液晶組成物
JPH0426679A (ja) *	1990-05-23	1992-01-29	Canon Inc	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
US5087672A (en) *	1990-06-13	1992-02-11	Minnesota Mining And Manufacturing Company	Fluorine-containing acrylate and methacrylate side-chain liquid crystal monomers and polymers
US5262082A (en) *	1992-04-28	1993-11-16	Minnesota Mining And Manufacturing Company	Ferroelectric liquid crystal compounds having perfluoroether terminal portions

1992
- 1992-04-28 US US07/875,223 patent/US5262082A/en not_active Expired - Lifetime
1993
- 1993-04-16 US US08/045,283 patent/US5437812A/en not_active Expired - Lifetime
- 1993-04-26 FI FI945069A patent/FI945069A0/fi unknown
- 1993-04-26 CA CA002133652A patent/CA2133652A1/en not_active Abandoned
- 1993-04-26 WO PCT/US1993/003925 patent/WO1993022396A1/en active IP Right Grant
- 1993-04-26 DE DE69332190T patent/DE69332190T2/de not_active Expired - Fee Related
- 1993-04-26 JP JP51944993A patent/JP3515109B2/ja not_active Expired - Fee Related
- 1993-04-26 EP EP93910823A patent/EP0638112B1/en not_active Expired - Lifetime
- 1993-04-27 MX MX9302467A patent/MX9302467A/es not_active IP Right Cessation
- 1993-04-27 TW TW082103260A patent/TW253906B/zh active
- 1993-04-28 MY MYPI93000785A patent/MY108861A/en unknown
1994
- 1994-10-27 KR KR1019940703830A patent/KR100271086B1/ko not_active Expired - Fee Related

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1991000897A1 (de) *	1989-07-11	1991-01-24	MERCK Patent Gesellschaft mit beschränkter Haftung	Chirale oder achirale ringverbindungen

Also Published As

Publication number	Publication date
CA2133652A1 (en)	1993-11-11
MX9302467A (es)	1994-06-30
EP0638112A1 (en)	1995-02-15
KR950701375A (ko)	1995-03-23
MY108861A (en)	1996-11-30
FI945069A7 (fi)	1994-10-27
JP3515109B2 (ja)	2004-04-05
WO1993022396A1 (en)	1993-11-11
EP0638112B1 (en)	2002-08-07
DE69332190D1 (de)	2002-09-12
US5437812A (en)	1995-08-01
FI945069L (fi)	1994-10-27
US5262082A (en)	1993-11-16
TW253906B (ko)	1995-08-11
FI945069A0 (fi)	1994-10-27
DE69332190T2 (de)	2003-05-08
JPH07506368A (ja)	1995-07-13

Publication	Publication Date	Title
KR100271086B1 (en)	2000-11-01	Liquid crystal compounds having perfluoroether terminal portions
GB9211427D0 (en)	1992-07-15	Liquid crystal lens circuit
ZA944977B (en)	1995-05-02	Liquid filter
GB2274922B (en)	1996-10-23	Liquid crystal projector
GB2263982B (en)	1996-02-28	Ferroelctric liquid crystals
GB2274649B (en)	1996-11-27	Liquid crystal siloxanes
GB9223741D0 (en)	1992-12-23	Liquid crystal device
EP0498622A3 (en)	1993-03-17	Liquid vaporizer-feeder
GB9318776D0 (en)	1993-10-27	Liquid crystal devices
GB9305770D0 (en)	1993-05-05	Filters for liquid
GB9201124D0 (en)	1992-03-11	Liquid crystal lens circuit
EP0566908A3 (en)	1994-09-07	Liquid filter
GB2274519B (en)	1996-08-21	Liquid crystal devices
EP0422996A3 (en)	1992-06-17	Liquid crystal compound
EP0439185A3 (en)	1991-12-04	Liquid crystal compound
GB2264713B (en)	1996-09-25	Liquid crystal device
GB9226527D0 (en)	1993-02-10	Liquid compositions
EP0529398A3 (en)	1993-04-28	Liquid filter
GB9411233D0 (en)	1994-07-27	Liquid crystal compositions
EP0435240A3 (en)	1991-09-18	Liquid crystal compound
ZA948435B (en)	1995-06-29	Liquid filter structure
EP0445037A3 (en)	1992-03-18	Liquid crystal compound
GB9012968D0 (en)	1990-08-01	Liquid crystal thiol compounds
GB9027103D0 (en)	1991-02-06	Liquid crystal mixtures
EP0425366A3 (en)	1992-01-02	Liquid crystal compound

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