WO1998052905A1 - New polymerisable liquid crystalline compounds - Google Patents

New polymerisable liquid crystalline compounds Download PDF

Info

Publication number
WO1998052905A1
WO1998052905A1 PCT/IB1998/000789 IB9800789W WO9852905A1 WO 1998052905 A1 WO1998052905 A1 WO 1998052905A1 IB 9800789 W IB9800789 W IB 9800789W WO 9852905 A1 WO9852905 A1 WO 9852905A1
Authority
WO
WIPO (PCT)
Prior art keywords
coo
alkyl
ooc
formula
represent
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.)
Ceased
Application number
PCT/IB1998/000789
Other languages
English (en)
French (fr)
Inventor
Carsten Benecke
Teodor Lukac
Angela Ohlemacher
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.)
Rolic Technologies Ltd
Original Assignee
Rolic AG
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.)
Filing date
Publication date
Application filed by Rolic AG filed Critical Rolic AG
Priority to HK00104492.5A priority Critical patent/HK1026195B/en
Priority to JP55018298A priority patent/JP2001527570A/ja
Priority to AU72276/98A priority patent/AU7227698A/en
Priority to EP98919404A priority patent/EP0983225B1/en
Priority to DE69820612T priority patent/DE69820612T2/de
Priority to KR1019997010737A priority patent/KR100566684B1/ko
Publication of WO1998052905A1 publication Critical patent/WO1998052905A1/en
Priority to US09/443,214 priority patent/US6395351B1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
    • C07C69/54—Acrylic acid esters; Methacrylic acid esters
    • 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
    • C07C69/94—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic 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
    • C09K19/3059—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon triple bonds
    • 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
    • C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
    • C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers 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
    • C09K19/38—Polymers
    • 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
    • C09K19/38—Polymers
    • C09K19/3833—Polymers with mesogenic groups in the side chain
    • C09K19/3842—Polyvinyl derivatives
    • C09K19/3852—Poly(meth)acrylate derivatives
    • 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
    • C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
    • 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
    • C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
    • C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
    • 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
    • C09K2019/0477—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by the positioning of substituents on phenylene
    • C09K2019/0481—Phenylene substituted in meta position
    • 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
    • C09K2019/0477—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by the positioning of substituents on phenylene
    • C09K2019/0485—Phenylene substituted in ortho position
    • 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
    • C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition

Definitions

  • This invention relates to new photo-crosslinkable liquid crystalline compounds, liquid crystalline mixtures which contain such compounds, and their use in the cross-linked condition as optical components.
  • Photo cross-linkable liquid crystals which are provided with an appropriate amount of a photoinitiator, can be oriented on a substrate or in a cell by suitable orienting layers or in a field and then in this state can be cross-linked by irradiation with light of a suitable wavelength.
  • the liquid crystal orientation in the structure thus produced is maintained, even at high temperatures.
  • Optical components such as waveguides, optical grids, filters and retarders, piezoelectric cells and cells with non-linear optical (NLO) properties etc. may therefore be produced using this procedure.
  • Such optical elements may be used, for example, for frequency doubling (SHG) or in colour filters.
  • optical properties of the liquid crystal materials used in the manufacture of the aforementioned optical components such as birefringence, refractive indices, transparency, etc. are selected according to the field of application in which they are to be used.
  • photo-crosslinkable liquid crystals are also suitable as glass fibre cladding for optical data transmission.
  • Photo-crosslinkable liquid crystals exhibit anisotropic thermal conductivity, enabling heat to flow in certain directions. The use of such materials reduces the thenrial coefficients of expansion and reduces microdistortion losses. This results in increased mechanical stability.
  • Liquid crystal media used in the manufacture of optical components are generally used in the form of liquid crystal mixtures. It is desirable that liquid crystal components are chemically and thermally stable, readily soluble in conventional solvents, and stable to electrical fields and electromagnetic radiation. They should have a suitable mesophase in the temperature range of from approx. 25° to approx. +100°C, particularly from approx.
  • liquid crystals are usually used as mixtures of several components, it is important for the components to be well miscible with one another.
  • a first aspect of the present invention provides compounds with the general formula I:
  • a and B are independent ring systems with the formulae a , a or b, a2
  • one or two non-adjacent CH groups may be replaced by oxygen, and whereby, in the 1 ,4-phenylene ring, one or two non-adjacent CH groups may be replaced by nitrogen;
  • L 1, TL , jL 3 represent, independently, hydrogen, C]-C 20 -alkyl, C ⁇ -C 2 o-alkenyl,
  • Z Z 2 , Z 3 represent, independently, a single bond, -CH CH 2 -, -CH O-, -OCH 2 -, -COO-, -OOC-, -(CH 2 ) 4 -, -O(CH 2 ) 3 -. -(CH 2 ) 3 O- or -C ⁇ C-;
  • S , S represent, independently, a spacer unit, such as a straight chain or branched alkylene grouping -(CH 2 ) r , substituted if necessary singly or multiply with, for example, fluorine, or -((CH 2 ) 2 -O) r -, or a chain with the formula -(CH 2 ) r -Y-(CH 2 ) s -, where Y represents a single bond or a linking functional group such as -O-, -COO-, -OOC-, -NR 1 -, NR !
  • Ph represents a phenyl group
  • R' represents methyl, ethyl, propyl, butyl or pentyl
  • R" represents methyl, methoxy, cyano or halogen
  • a structural unit with the above-mentioned formulae a 1 and a 2 and in which Z 2 represents a single bond have been found to exhibit relatively high clearing points and can be processed at room temperature, preferably as components of liquid crystal mixtures. It is also possible to orientate and structure the compounds or mixtures thereof without the formation of domains. As a component of a LC mixture, they are able to improve the orientability of the liquid crystal mixture on orientation layers thereby improving the contrast of optical display devices. In addition they exhibit extremely good thermal and long-term stability.
  • C_-C o-alkyl, C.-C 0 -alkoxy, CrC 20 -alkoxy carbonyl, C ⁇ -C 20 -alkylcarbonyl, C ⁇ -C 20 -alkylcarbonyloxy it should be understood to mean, in the context of this invention, straight or branched chain saturated hydrocarbon residues, with up to 20 carbon atoms, e.g.
  • C ⁇ -C 0 -alkenyl it should be understood to mean, in the context of this invention, alkenyl groups with 3 to 20 carbon atoms, such as 2E-alkenyl, 3Z-alkenyl, 4E-alkenyl and alkenyl with a terminal double bond, e.g. alkyl, 3-butenyl, 4-pentenyl, 5-hexenyl, 6-heptenyl, 7-octenyl, 8-nonenyl, 9-decenyl, 10-undecenyl and the like.
  • alkenyls with a terminal double bond having 3 to 12 carbon atoms.
  • halogen it should be understood to mean, in the context of this invention, fluorine, chlorine, bromine, iodine. Compounds containing fluorine and chlorine are particularly preferred.
  • Preferred compounds with formula I are compounds with formulae I-A to I-F
  • one or two non-adjacent CH 2 groups of the trans- 1,4-cyclohexylene ring may be replaced by oxygen and one or two non-adjacent CH groups of the 1 ,4-phenylene ring, may be replaced by nitrogen;
  • L 11 , L 12 , L 13 represent, independently, hydrogen, C ⁇ -C 2 o-alkyl, C ⁇ -C 0 -alkenyl,
  • Z 4 represents a single bond, -CH 2 CH 2 -, -CH 2 O-, -OCH 2 -, -COO-, -OOC-,
  • Z 5 represents a single bond, -CH 2 CH 2 -, -CH 2 O-, -OCH 2 -, -COO-, -OOC-, or
  • L n , L 12 , L 13 represent, independently, hydrogen, C ⁇ -C 12 -alkyl, C ⁇ -C 1 -alkenyl, C ⁇ -C ]2 -alkoxy, C r C ⁇ 2 -alkoxycarbonyl, formyl, C ⁇ -C 12 -alkylcarbonyl, C_-Ci 2 -alkylcarbonyloxy, fluorine, chlorine, cyano or nitro; represents -CH 2 CH 2 -, -OCH 2 , -COO-, -OOC-; Z 5 represents a single bond, -CH 2 CH 2 -, -COO-, -OOC-, or -C ⁇ C-;
  • CH 2 CH-COO-
  • CH 2 C(CH 3 )-COO-
  • CH 2 C(Cl)-COO-
  • L represents hydrogen, C_-C ⁇ 2 -alkyl, C ⁇ -C
  • Z 4 represents -CH 2 -CH 2 -, -OCH 2 -, -COO-, -OOC-; particularly -COO-;
  • Z 5 represents a single bond, -CH 2 CH 2 -, -COO-, -OOC- or -C ⁇ C-; particularly a single bond;
  • Z 5 represents a single bond, -CH 2 CH 2 -, -COO-, -OOC- or -C ⁇ C-;
  • L represent, independently, hydrogen, C ⁇ -C ⁇ 2 -alkyl, C ⁇ -C ⁇ 2 -alkenyl, Ci-C ⁇ -alkoxy, C]-C ⁇ 2 -alkoxy-carbonyl, formyl, C ⁇ -C ⁇ 2 -alkylcarbonyl,
  • CH 2 CH-COO-
  • CH 2 C(CH 3 )-COO-
  • CH 2 C(Cl)-COO-
  • the essential structural element of the compounds with formula I is a structural
  • R 2 represents C ⁇ -C 2 o-alkyl, especially C ⁇ -C] 2 -alkyl.
  • the compounds of formula I may be used alone, in the form of mixtures with other compounds of formula I or with other liquid crystal components.
  • Preferred liquid crystalline mixtures contain at least two components.
  • these additional liquid crystalline components may contain a photo-crosslinkable group.
  • One or more chiral compounds may also be contained in the mixture.
  • the good solubility and miscibility of the compounds with Formula I means that liquid crystal mixtures containing a high proportion of compound of Formula I may be prepared. Such mixtures may contain up to 100% by weight of the compounds of formula I.
  • mixtures according to the invention preferably contain not only one or more compounds with Formula I, but also one or more compounds from the group of compounds with the general formulae
  • X represents hydrogen, C ⁇ -C 20 -alkyl, C ⁇ -C 20 -alkenyl, C ⁇ -C 20 -alkyloxy, C ⁇ -C 20 -alkyloxy carbonyl, formyl, C ⁇ -C 20 -alkyl carbonyl, C ⁇ -C 20 -alkyl carbonyloxy, fluorine, chlorine, bromine, cyano or nitro;
  • m' represents a whole number from 2 to 20;
  • t represents a whole number from 2 to 12;
  • Z represents -COO-, -OOC-, -OCH 2 -, -CH 2 O-, -O(CH 2 ) 3 -, -OOC(CH 2 ) 2 -,
  • D represents 1,4-phenylene, trans- 1,4-cyclohexylene, pyridine-2,5-diyl, pyrimidine- -2,5-diyl or trans- 1,4-cyclohexylene- 1,4-phenylene;
  • Asymmetric compounds containing phenyl ester residues which are variously substituted on both sides of the 4-(trans-4-hydroxycyclohexyl)phenol were prepared using a two-step synthesis analogous to that of Scheme 1. Mono-esterification of the more reactive phenolic hydroxy group of the 4-(trans-4-hydroxycyclohexyl)phenol and subsequent esterification with a differently substituted phenyl carbonic acid produced the asymmetrical substituted diester. The following 4-(trans-4-hydroxycyclohexyl)-phenols mono-substituted in
  • R C ⁇ -C20-Alkyl, preferably Ci-C 12- Alkyl
  • the substituted 4-(trans-4-hydroxycyclohexyl)phenols used as the raw material were manufactured, for example, by the following methods: a) 2-allyl-4-(trans-4-hydroxycyclohexyl)phenol
  • the trans-4-(4-allyloxyphenyl)cyclohexanol used as raw material was manufactured by the following method:
  • the 4-(3-fluoro-4-hydroxyphenyl)cyclohexanone used as the raw material was manufactured by the following method:
  • a mixture comprising 2 m of acetic acid and 23.83 g (70 mmols) of 8-(4-benzyloxy-3-fluorophenyl)-l,4-dioxaspiro[4.5]dec-7-ene in 200 ml of toluene was hydrated at room temperature in the presence of 2.38 g 10% palladium/C hydrating catalyst. After the hydrogen uptake was complete the reaction mixture was filtered through dicalcite. The solvent was removed to give the crude product.
  • Example lb In an analogous fashion to Example lb the product was prepared using 6.13 g (20 mmols) of 2-hydroxy-5-(4-oxocyclohexyl)benzoic acid pentyl ester and 0.76 g (200 mmols) NaBEU . Recrystallisation from isopropanol gave the 2-hydroxy- -5-(trans-4-hydroxycyclohexyl)benzoic acid pentyl ester product.
  • the hydroxy-5-(4-oxocyclohexyl)benzoic acid pentyl ester used as the raw material was manufactured by the following method:
  • the acrylic acid trans-6-[4-[4-(4-hydroxycyclohexyl)phenylethynyl]phenoxy]- hexyl ester starting material was manufactured using a known method (A. Carpita, A. Lessi, R.
  • the acrylic acid trans-6-4'-(4-hydroxycyclohexyl)biphenyl-4-yloxyl]hexyl ester starting material was prepared using known methods by the Grignard coupling of 4-(4-bromophenyl)phenol and l,4-dioxaspiro[4.5]decan-8-one (similar to Example lb), followed by reduction of the keto group and Williamson etherification of the phenolic hydroxy group with acrylic acid 6-chlorohexyl ester (cf. Scheme 3).
  • the acrylic acid trans-6-[4-(4-hydroxycyclohexyl)phenoxy]hexyl ester starting material was obtained by Williamson etherification of 4-(trans-4-hydroxycyclohexyl)- phenol with acrylic acid 6-chlorohexyl ester (cf. Scheme 4).
  • the substituted 4-(trans- -4-hydroxycyclohexyl)phenols mentioned in Example 1 were also similarly alkylated.
  • a photoinitiator (IRGACURE, Ciba-Geigy) and 2% by weight of inhibitor (BHT) were added thereto.
  • the resulting mixture was dissolved in anisole (20% by weight), then spin-coated at 900 revolutions per minute on to a glass substrate that was coated with rubbed polyimide (SE 510, NISSAN).
  • SE 510, NISSAN rubbed polyimide
  • the layer was crosslinked in the vacuum cabinet at room temperature in a vacuum with xenon light (e.g. 30 minutes).
  • a parallel orientated nematic layer with a layer thickness of 1 ⁇ m and a birefringence of approx. 0.15 was produced. This layer acts as an optical retarder.
  • Example 7 2% by weight of IRGACURE and 2% by weight of BHT was added to a mixture having the same composition as that specified in Example 6. The resulting mixture was dissolved in anisole (20% by weight), spin coated at 900 revolutions per minute on to a glass sheet pre-coated with an orientation layer of methacryloyloxyethyl-3-(E)-[4-cyano- -4'-biphenyl]acrylate, which forms a photo polymerisable network (PPN).
  • This orientation layer has a predetermined pattern photolithographically formed by illuminating with linearly polarised light through a mask.
  • the new layer (on the PPN layer) was dried at 40°C on a heating bench, then exposed in the vacuum cabinet at room temperature in a vacuum with xenon light.
  • the registered original structure was maintained and accurately incorporated in the new network.
  • a clear birefringence ( ⁇ n) was detectable.
  • This layer acts as a spatially structured optical retarder.

Landscapes

  • 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)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Epoxy Compounds (AREA)
PCT/IB1998/000789 1997-05-22 1998-05-22 New polymerisable liquid crystalline compounds Ceased WO1998052905A1 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
HK00104492.5A HK1026195B (en) 1997-05-22 1998-05-22 New polymerisable liquid crystalline compounds
JP55018298A JP2001527570A (ja) 1997-05-22 1998-05-22 新規重合性液晶化合物
AU72276/98A AU7227698A (en) 1997-05-22 1998-05-22 New polymerisable liquid crystalline compounds
EP98919404A EP0983225B1 (en) 1997-05-22 1998-05-22 New polymerisable liquid crystalline compounds
DE69820612T DE69820612T2 (de) 1997-05-22 1998-05-22 Neue polymerisierbare flüssigkristalline verbindungen
KR1019997010737A KR100566684B1 (ko) 1997-05-22 1998-05-22 중합성 액정 화합물, 및 이를 포함하는 가교결합성 액정 혼합물 및 광학 부재
US09/443,214 US6395351B1 (en) 1997-05-22 1999-11-19 Polymerisable liquid crystalline compounds

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP97108259 1997-05-22
EP97108259.9 1997-05-22

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US09/443,214 Continuation US6395351B1 (en) 1997-05-22 1999-11-19 Polymerisable liquid crystalline compounds

Publications (1)

Publication Number Publication Date
WO1998052905A1 true WO1998052905A1 (en) 1998-11-26

Family

ID=8226813

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB1998/000789 Ceased WO1998052905A1 (en) 1997-05-22 1998-05-22 New polymerisable liquid crystalline compounds

Country Status (8)

Country Link
US (1) US6395351B1 (https=)
EP (1) EP0983225B1 (https=)
JP (1) JP2001527570A (https=)
KR (1) KR100566684B1 (https=)
CN (1) CN1213989C (https=)
AU (1) AU7227698A (https=)
DE (1) DE69820612T2 (https=)
WO (1) WO1998052905A1 (https=)

Cited By (62)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1046631A1 (en) * 1999-04-19 2000-10-25 Rolic AG Liquid crystalline compounds
WO2000063154A1 (en) * 1999-04-19 2000-10-26 Rolic Ag Liquid crystal compounds
GB2351734A (en) * 1999-06-30 2001-01-10 Merck Patent Gmbh Polymerizable mesogenic tolans
US6548127B1 (en) * 1998-01-27 2003-04-15 Rolic Ag Liquid-crystalline photocrosslinkable mixture
US6645397B2 (en) * 2000-06-26 2003-11-11 Fuji Photo Film Co., Ltd. Liquid crystal composition, color filter and optical film
US6673267B2 (en) * 1999-12-24 2004-01-06 Sumitomo Chemical Company, Limited Phenylacetylene compound, liquid crystal composition, polymer, optically anisotropic product, and liquid crystal or optical element
WO2004015464A1 (en) * 2002-08-07 2004-02-19 Fuji Photo Film Co., Ltd. Retarder and circular polarizer
WO2004033584A1 (de) * 2002-10-07 2004-04-22 Merck Patent Gmbh Flüssigkristalline medien enthaltend polymere
EP1506991A3 (en) * 2003-07-17 2005-08-10 Fuji Photo Film Co., Ltd. Liquid crystalline compound, liquid crystalline composition and retardation film
KR100694936B1 (ko) * 2000-07-20 2007-03-14 메르크 파텐트 게엠베하 중합성 메소제닉 톨란
JP2008239873A (ja) * 2007-03-28 2008-10-09 Dic Corp ビフェニル及びテルフェニル化合物、該化合物を含有する重合性液晶組成物
EP1873228A4 (en) * 2005-04-13 2009-04-22 Asahi Glass Co Ltd POLYMERIZABLE LIQUID CRYSTALLINE COMPOSITION, OPTICAL ANISOTROPIC MATERIAL, OPTICAL ELEMENT AND OPTICAL HEAD
WO2010143684A1 (ja) 2009-06-11 2010-12-16 富士フイルム株式会社 赤外光反射板、赤外光反射性合わせガラス、並びにコレステリック液晶層を有する積層体及び合わせガラス
WO2010143682A1 (ja) 2009-06-11 2010-12-16 富士フイルム株式会社 光反射膜の製造方法
WO2010143683A1 (ja) 2009-06-11 2010-12-16 富士フイルム株式会社 赤外光反射板、及び赤外光反射性合わせガラス
EP2362248A2 (en) 2010-01-27 2011-08-31 Fujifilm Corporation Infrared light reflecting plate, laminated interlayer film sheet for laminated glass and its production method, and laminated glass
CN102482242A (zh) * 2009-09-03 2012-05-30 住友化学株式会社 二环氧化合物、其制造方法和含有该二环氧化合物的组合物
WO2012111715A1 (ja) 2011-02-18 2012-08-23 富士フイルム株式会社 赤外光反射板並びに合わせガラス用積層中間膜シート及び合わせガラスとそれらの製造方法
WO2012124719A1 (ja) 2011-03-16 2012-09-20 富士フイルム株式会社 重合性化合物、重合性液晶組成物、高分子化合物およびフィルム
WO2013035733A1 (ja) 2011-09-08 2013-03-14 富士フイルム株式会社 重合性液晶化合物、重合性組成物、高分子材料、及びフィルム
JP2013112631A (ja) * 2011-11-28 2013-06-10 Dic Corp 重合性液晶化合物
WO2014045878A1 (ja) 2012-09-18 2014-03-27 富士フイルム株式会社 熱線カットフィルムおよびその製造方法、合わせガラス並びに熱線カット部材
WO2014061279A1 (ja) 2012-10-19 2014-04-24 日本化薬株式会社 熱線遮蔽シート
WO2014185518A1 (ja) 2013-05-16 2014-11-20 日本化薬株式会社 赤外線遮蔽シート及びその製造方法並びにその用途
WO2015050203A1 (ja) 2013-10-03 2015-04-09 富士フイルム株式会社 投映像表示用ハーフミラーおよびその製造方法、ならびに投映像表示システム
WO2015050256A1 (ja) 2013-10-04 2015-04-09 富士フイルム株式会社 コレステリック液晶層を含む熱圧着貼合用フィルムおよびその応用
US9715144B2 (en) 2007-12-21 2017-07-25 Rolic Ag Photoalignment composition
WO2017130683A1 (ja) 2016-01-29 2017-08-03 富士フイルム株式会社 ハーフミラーおよび画像表示機能付きミラー
WO2017183428A1 (ja) 2016-04-21 2017-10-26 富士フイルム株式会社 画像表示機能付きミラーおよびハーフミラー
WO2018084076A1 (ja) 2016-11-04 2018-05-11 富士フイルム株式会社 ウインドシールドガラス、ヘッドアップディスプレイシステム、およびハーフミラーフィルム
WO2018146958A1 (ja) 2017-02-09 2018-08-16 富士フイルム株式会社 ハーフミラー、ハーフミラーの製造方法、および画像表示機能付きミラー
WO2018198559A1 (ja) 2017-04-28 2018-11-01 富士フイルム株式会社 画像表示機能付き防眩ミラー
WO2019009252A1 (ja) 2017-07-04 2019-01-10 富士フイルム株式会社 ハーフミラー
WO2019050019A1 (ja) 2017-09-07 2019-03-14 富士フイルム株式会社 投映像表示用ハーフミラーフィルム、投映像表示用の合わせガラス、および、画像表示システム
US10386569B2 (en) 2015-02-10 2019-08-20 Fujifilm Corporation Optical member, optical element, liquid crystal display device, and near-to-eye optical member
WO2019163969A1 (ja) 2018-02-23 2019-08-29 富士フイルム株式会社 画像表示用合わせガラスの製造方法、画像表示用合わせガラス、および、画像表示システム
WO2019188846A1 (ja) 2018-03-29 2019-10-03 富士フイルム株式会社 画像形成方法
WO2020008961A1 (ja) 2018-07-02 2020-01-09 富士フイルム株式会社 加飾フィルム、加飾方法、加飾成型体の製造方法、及び、加飾成型フィルム
WO2020080355A1 (ja) 2018-10-17 2020-04-23 富士フイルム株式会社 投映像表示用部材、ウインドシールドガラスおよびヘッドアップディスプレイシステム
WO2020122023A1 (ja) 2018-12-10 2020-06-18 富士フイルム株式会社 投映像表示用部材、ウインドシールドガラスおよびヘッドアップディスプレイシステム
WO2020179787A1 (ja) 2019-03-06 2020-09-10 富士フイルム株式会社 投映像表示用積層フィルム、投映像表示用の合わせガラス、および、画像表示システム
WO2020194831A1 (ja) 2019-03-28 2020-10-01 富士フイルム株式会社 インクジェット記録用インクセット及び画像記録方法
US10816709B2 (en) 2014-12-19 2020-10-27 Nippon Kayaku Kabushiki Kaisha Light reflection film and laminate having the light reflection film
WO2020262474A1 (ja) 2019-06-27 2020-12-30 富士フイルム株式会社 成型用加飾フィルム、成型物、及びディスプレイ
WO2021059879A1 (ja) 2019-09-27 2021-04-01 富士フイルム株式会社 画像記録方法
WO2021060402A1 (ja) 2019-09-27 2021-04-01 富士フイルム株式会社 ヘッドアップディスプレイ用プロジェクター
WO2021200655A1 (ja) 2020-03-30 2021-10-07 富士フイルム株式会社 反射フィルム、ウインドシールドガラスおよびヘッドアップディスプレイシステム
WO2021220794A1 (ja) 2020-04-28 2021-11-04 富士フイルム株式会社 化合物、液晶組成物、硬化物およびフィルム
WO2021246402A1 (ja) 2020-06-03 2021-12-09 富士フイルム株式会社 反射フィルム、合わせガラスの製造方法、および、合わせガラス
WO2022075184A1 (ja) 2020-10-09 2022-04-14 富士フイルム株式会社 反射フィルム、ウインドシールドガラス、および、ヘッドアップディスプレイシステム
WO2022123946A1 (ja) 2020-12-09 2022-06-16 富士フイルム株式会社 反射フィルム、ウインドシールドガラスおよびヘッドアップディスプレイシステム
WO2022138142A1 (ja) 2020-12-25 2022-06-30 富士フイルム株式会社 画像記録方法及びインクジェット記録物
WO2023054324A1 (ja) 2021-09-30 2023-04-06 富士フイルム株式会社 ヘッドアップディスプレイシステム及び輸送機
WO2023080115A1 (ja) 2021-11-05 2023-05-11 富士フイルム株式会社 虚像表示装置、ヘッドアップディスプレイシステム及び輸送機
WO2023085370A1 (ja) 2021-11-12 2023-05-19 富士フイルム株式会社 画像記録物及び画像記録方法
WO2023200018A1 (ja) 2022-04-15 2023-10-19 富士フイルム株式会社 反射フィルム、積層体、ウインドシールドガラス、画像表示システム
WO2023248719A1 (ja) 2022-06-21 2023-12-28 富士フイルム株式会社 画像記録物及び画像記録物の製造方法、並びに、加飾成形体
WO2024106459A1 (ja) 2022-11-17 2024-05-23 富士フイルム株式会社 投映像表示用積層フィルム、投映像表示用合わせガラス、投映像表示システム
US12158655B2 (en) 2019-03-28 2024-12-03 Nippon Kayaku Kabushiki Kaisha Optical film and eyewear
WO2025013896A1 (ja) 2023-07-11 2025-01-16 富士フイルム株式会社 組成物、光学異方性層、硬化膜、回折素子
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
WO2025018426A1 (ja) 2023-07-20 2025-01-23 富士フイルム株式会社 コレステリック液晶層の製造方法、コレステリック液晶層、反射フィルム、合わせガラス、ヘッドアップディスプレイシステム、組成物

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001053248A1 (en) * 2000-01-21 2001-07-26 Dainippon Ink And Chemicals, Inc. Polymerizable composition showing liquid-crystal phase and optically anisotropic object made with the same
DE10016524A1 (de) * 2000-04-03 2001-10-04 Basf Ag Polymerisierbare Flüssigkristalle
JP4836335B2 (ja) * 2000-04-25 2011-12-14 住友化学株式会社 フェニルアセチレン重合物、光学異方体及び光学又は液晶用素子
DE10025782A1 (de) * 2000-05-26 2001-12-06 Basf Ag Flüssigkristalline Stoffgemenge
JP5186116B2 (ja) * 2006-06-12 2013-04-17 富士フイルム株式会社 化合物、それを含有する液晶組成物、異方性材料、偏光板保護フィルム、光学補償フィルムならびに液晶表示装置
KR101436795B1 (ko) 2006-09-13 2014-09-03 롤리크 아게 체적 광-정렬 지연판
JP5140991B2 (ja) * 2006-10-31 2013-02-13 Ｄｉｃ株式会社 重合性液晶化合物
EP2094815B1 (en) * 2006-12-22 2012-06-27 Rolic AG Patternable liquid crystal polymer comprising thio-ether units
US8425990B2 (en) * 2007-02-23 2013-04-23 Zeon Corporation Liquid crystalline compound, liquid crystalline composition, optical film, and optical laminate
JP5186120B2 (ja) * 2007-03-05 2013-04-17 富士フイルム株式会社 化合物、それを含有する液晶組成物、異方性材料、偏光板保護フィルム、光学補償フィルムならびに液晶表示装置
JP5345293B2 (ja) * 2007-03-29 2013-11-20 株式会社Ａｄｅｋａ 重合性化合物及び重合性組成物
KR101676231B1 (ko) * 2007-08-30 2016-11-14 메르크 파텐트 게엠베하 액정 디스플레이
KR101499238B1 (ko) * 2008-08-07 2015-03-05 삼성디스플레이 주식회사 액정 표시 장치
JP2010196016A (ja) * 2009-02-27 2010-09-09 Mitsubishi Electric Corp 樹脂組成物及び樹脂硬化物
JP2010196015A (ja) * 2009-02-27 2010-09-09 Mitsubishi Electric Corp 樹脂組成物及び樹脂硬化物
TWI490316B (zh) 2009-07-09 2015-07-01 Rolic Ag 用於光學或光電元件之含酯基液晶
EP2272937A1 (en) 2009-07-09 2011-01-12 Rolic AG Ester group containing compounds for optical or electro optical devices
KR20110021587A (ko) * 2009-08-26 2011-03-04 삼성전자주식회사 액정 표시 장치 및 그 제조 방법
US8257639B2 (en) * 2009-09-22 2012-09-04 Kent State University Method of making stimuli responsive liquid crystal-polymer composite fibers
JP6051566B2 (ja) * 2012-04-05 2016-12-27 Dic株式会社 飽和環構造を有する重合性化合物
DE102015000119A1 (de) * 2014-01-24 2015-07-30 Merck Patent Gmbh Verfahren zur Herstellung von Bis-[4-(6-acryloyloxy-hexyl)-phenyl]cyclohexan-1,4- dicarbonsäureester
JP6080884B2 (ja) 2014-03-28 2017-02-15 富士フイルム株式会社 重合性化合物、ポリマー、重合性組成物、フィルム、および投映像表示用ハーフミラー
JP6343348B2 (ja) * 2014-09-05 2018-06-13 富士フイルム株式会社 重合性化合物、ポリマー、重合性組成物、およびフィルム
EP3199561B1 (en) * 2014-09-25 2019-01-09 FUJIFILM Corporation Polymerizable composition comprising polymerizable compounds, film, and half mirror for projected-image display
WO2016143883A1 (ja) 2015-03-12 2016-09-15 富士フイルム株式会社 重合性組成物、フィルム、および投映像表示用ハーフミラー
CN105037401B (zh) * 2015-07-23 2018-12-14 暨南大学 一种格氏反应用镁屑的处理方法
CN109477930A (zh) 2016-07-29 2019-03-15 罗利克技术有限公司 在液晶聚合物材料上产生取向的方法
CN107573212B (zh) * 2017-10-13 2020-08-04 宁夏中星显示材料有限公司 反式4-烷基环己基苯结构液晶中间体及单体的合成方法
CN118259397A (zh) 2019-07-24 2024-06-28 罗利克技术有限公司 可光致配向的正c板延迟器

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2155465A (en) * 1984-01-23 1985-09-25 Dainippon Ink & Chemicals Tolan-type nematic liquid crystalline compounds
WO1993022397A1 (en) * 1992-04-27 1993-11-11 Merck Patent Gmbh Electrooptical liquid crystal system
EP0648827A1 (en) * 1993-10-15 1995-04-19 MERCK PATENT GmbH Reactive liquid crystal compounds
WO1995022586A1 (de) * 1994-02-19 1995-08-24 Basf Aktiengesellschaft Neue polymerisierbare flüssigkristalline verbindungen
DE4408171A1 (de) * 1994-03-11 1995-09-14 Basf Ag Neue polymerisierbare flüssigkristalline Verbindungen
EP0689065A1 (de) * 1994-06-24 1995-12-27 F. Hoffmann-La Roche AG Optisches Bauelement

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2636684C3 (de) 1976-08-14 1980-06-19 Merck Patent Gmbh, 6100 Darmstadt Phenylcyclohexanderivate und ihre Verwendung in flüssigkristallinen Dielektrika
DE2853728A1 (de) 1978-12-13 1980-07-17 Merck Patent Gmbh Fluessigkristalline carbonsaeureester, verfahren zu ihrer herstellung, diese enthaltende dielektrika und elektrooptisches anzeigeelement
EP0122389B1 (de) 1983-03-16 1987-08-05 F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft Flüssigkristallkomponenten mit einer Alkenylseitenkette
DE3667170D1 (de) 1985-03-26 1990-01-04 Hoffmann La Roche Alkenylsubstituierte phenylisothiocyanate und benzonitrile.
DE3534778A1 (de) 1985-09-30 1987-04-02 Hoechst Ag Chirale ester mesogener carbonsaeuren, ein verfahren zu deren herstellung und ihre verwendung als dotierstoff in fluessigkristall-phasen
DE3604462A1 (de) 1986-02-13 1987-08-20 Merck Patent Gmbh Smektische fluessigkristalline phasen
US4696990A (en) 1986-03-31 1987-09-29 Eastman Kodak Company Novel photocrosslinkable liquid crystalline polymers
KR100257886B1 (ko) 1993-01-29 2000-06-01 손욱 고분자 액정 복합체
US5518652A (en) 1993-07-05 1996-05-21 Merck Patent Gesellschaft Mit Beschrankter Haftung Liquid crystalline copolymer
US5567349A (en) 1994-03-30 1996-10-22 Hoffmann-La Roche Inc. Photo cross-linkable liquid crystals
US5593617A (en) 1994-09-12 1997-01-14 Hoffmann-Laroche Inc. Photochemically polymerizable liquid crystals
GB2298202B (en) 1995-02-24 1998-09-16 Merck Patent Gmbh Chiral polymerizable binaphthol derivatives
US5707544A (en) 1995-06-07 1998-01-13 Rolic Ag Chromophore-containing photo cross-linkable liquid crystals
DE19520704A1 (de) 1995-06-09 1996-12-12 Basf Ag Polymerisierbare chirale Verbindungen und deren Verwendung
DE59605841D1 (de) 1995-07-28 2000-10-12 Rolic Ag Zug Photovernetzbare Chirale Dotierstoffe
US6174457B1 (en) * 1996-09-27 2001-01-16 Chisso Corporation Compound having alkadienyl group as side chain, and liquid crystal composition using same

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2155465A (en) * 1984-01-23 1985-09-25 Dainippon Ink & Chemicals Tolan-type nematic liquid crystalline compounds
WO1993022397A1 (en) * 1992-04-27 1993-11-11 Merck Patent Gmbh Electrooptical liquid crystal system
EP0648827A1 (en) * 1993-10-15 1995-04-19 MERCK PATENT GmbH Reactive liquid crystal compounds
WO1995022586A1 (de) * 1994-02-19 1995-08-24 Basf Aktiengesellschaft Neue polymerisierbare flüssigkristalline verbindungen
DE4408171A1 (de) * 1994-03-11 1995-09-14 Basf Ag Neue polymerisierbare flüssigkristalline Verbindungen
EP0689065A1 (de) * 1994-06-24 1995-12-27 F. Hoffmann-La Roche AG Optisches Bauelement

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
A. L. WILDS: "Steroid analogs lacking ring C.", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY., vol. 76, no. 7, - 5 April 1954 (1954-04-05), DC US, pages 1733 - 1736, XP002063197 *
KELLY S M: "THE SYNTHESIS AND LIQUID CRYSTAL TRANSITION TEMPERATURES OF SOME WEAKLY POLAR NEMATIC TRANS-4-SUBSTITUTED-CYCLOHEXYL (E)-ALK-2- ENOATES", LIQUID CRYSTALS, vol. 17, no. 2, 1 August 1994 (1994-08-01), pages 211 - 225, XP000460892 *

Cited By (70)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6548127B1 (en) * 1998-01-27 2003-04-15 Rolic Ag Liquid-crystalline photocrosslinkable mixture
EP1046631A1 (en) * 1999-04-19 2000-10-25 Rolic AG Liquid crystalline compounds
WO2000063154A1 (en) * 1999-04-19 2000-10-26 Rolic Ag Liquid crystal compounds
US6746729B1 (en) 1999-04-19 2004-06-08 Rolic Ag Liquid crystal compounds
GB2351734A (en) * 1999-06-30 2001-01-10 Merck Patent Gmbh Polymerizable mesogenic tolans
US6514578B1 (en) 1999-06-30 2003-02-04 Merck Patent Gesellschaft Mit Beschrankter Haftung Polymerizable mesogenic tolanes
GB2351734B (en) * 1999-06-30 2004-09-01 Merck Patent Gmbh Polymerizable mesogenic tolans
US6673267B2 (en) * 1999-12-24 2004-01-06 Sumitomo Chemical Company, Limited Phenylacetylene compound, liquid crystal composition, polymer, optically anisotropic product, and liquid crystal or optical element
US6645397B2 (en) * 2000-06-26 2003-11-11 Fuji Photo Film Co., Ltd. Liquid crystal composition, color filter and optical film
KR100694936B1 (ko) * 2000-07-20 2007-03-14 메르크 파텐트 게엠베하 중합성 메소제닉 톨란
WO2004015464A1 (en) * 2002-08-07 2004-02-19 Fuji Photo Film Co., Ltd. Retarder and circular polarizer
US7473446B2 (en) 2002-08-07 2009-01-06 Fujifilm Corporation Retarder and circular polarizer
WO2004033584A1 (de) * 2002-10-07 2004-04-22 Merck Patent Gmbh Flüssigkristalline medien enthaltend polymere
EP1506991A3 (en) * 2003-07-17 2005-08-10 Fuji Photo Film Co., Ltd. Liquid crystalline compound, liquid crystalline composition and retardation film
EP1873228A4 (en) * 2005-04-13 2009-04-22 Asahi Glass Co Ltd POLYMERIZABLE LIQUID CRYSTALLINE COMPOSITION, OPTICAL ANISOTROPIC MATERIAL, OPTICAL ELEMENT AND OPTICAL HEAD
JP2008239873A (ja) * 2007-03-28 2008-10-09 Dic Corp ビフェニル及びテルフェニル化合物、該化合物を含有する重合性液晶組成物
US10558089B2 (en) 2007-12-21 2020-02-11 Rolic Ag Photoalignment composition
US9715144B2 (en) 2007-12-21 2017-07-25 Rolic Ag Photoalignment composition
WO2010143683A1 (ja) 2009-06-11 2010-12-16 富士フイルム株式会社 赤外光反射板、及び赤外光反射性合わせガラス
WO2010143684A1 (ja) 2009-06-11 2010-12-16 富士フイルム株式会社 赤外光反射板、赤外光反射性合わせガラス、並びにコレステリック液晶層を有する積層体及び合わせガラス
WO2010143682A1 (ja) 2009-06-11 2010-12-16 富士フイルム株式会社 光反射膜の製造方法
CN102482242B (zh) * 2009-09-03 2014-07-16 住友化学株式会社 二环氧化合物、其制造方法和含有该二环氧化合物的组合物
CN102482242A (zh) * 2009-09-03 2012-05-30 住友化学株式会社 二环氧化合物、其制造方法和含有该二环氧化合物的组合物
EP2362248A2 (en) 2010-01-27 2011-08-31 Fujifilm Corporation Infrared light reflecting plate, laminated interlayer film sheet for laminated glass and its production method, and laminated glass
WO2012111715A1 (ja) 2011-02-18 2012-08-23 富士フイルム株式会社 赤外光反射板並びに合わせガラス用積層中間膜シート及び合わせガラスとそれらの製造方法
WO2012124719A1 (ja) 2011-03-16 2012-09-20 富士フイルム株式会社 重合性化合物、重合性液晶組成物、高分子化合物およびフィルム
WO2013035733A1 (ja) 2011-09-08 2013-03-14 富士フイルム株式会社 重合性液晶化合物、重合性組成物、高分子材料、及びフィルム
JP2013112631A (ja) * 2011-11-28 2013-06-10 Dic Corp 重合性液晶化合物
WO2014045878A1 (ja) 2012-09-18 2014-03-27 富士フイルム株式会社 熱線カットフィルムおよびその製造方法、合わせガラス並びに熱線カット部材
WO2014061279A1 (ja) 2012-10-19 2014-04-24 日本化薬株式会社 熱線遮蔽シート
WO2014185518A1 (ja) 2013-05-16 2014-11-20 日本化薬株式会社 赤外線遮蔽シート及びその製造方法並びにその用途
WO2015050203A1 (ja) 2013-10-03 2015-04-09 富士フイルム株式会社 投映像表示用ハーフミラーおよびその製造方法、ならびに投映像表示システム
WO2015050256A1 (ja) 2013-10-04 2015-04-09 富士フイルム株式会社 コレステリック液晶層を含む熱圧着貼合用フィルムおよびその応用
US10816709B2 (en) 2014-12-19 2020-10-27 Nippon Kayaku Kabushiki Kaisha Light reflection film and laminate having the light reflection film
US10386569B2 (en) 2015-02-10 2019-08-20 Fujifilm Corporation Optical member, optical element, liquid crystal display device, and near-to-eye optical member
WO2017130683A1 (ja) 2016-01-29 2017-08-03 富士フイルム株式会社 ハーフミラーおよび画像表示機能付きミラー
WO2017183428A1 (ja) 2016-04-21 2017-10-26 富士フイルム株式会社 画像表示機能付きミラーおよびハーフミラー
WO2018084076A1 (ja) 2016-11-04 2018-05-11 富士フイルム株式会社 ウインドシールドガラス、ヘッドアップディスプレイシステム、およびハーフミラーフィルム
WO2018146958A1 (ja) 2017-02-09 2018-08-16 富士フイルム株式会社 ハーフミラー、ハーフミラーの製造方法、および画像表示機能付きミラー
WO2018198559A1 (ja) 2017-04-28 2018-11-01 富士フイルム株式会社 画像表示機能付き防眩ミラー
WO2019009252A1 (ja) 2017-07-04 2019-01-10 富士フイルム株式会社 ハーフミラー
EP4312066A2 (en) 2017-09-07 2024-01-31 FUJIFILM Corporation One-way mirror film for displaying projected images, laminated glass for displaying projected images, and image display system
WO2019050019A1 (ja) 2017-09-07 2019-03-14 富士フイルム株式会社 投映像表示用ハーフミラーフィルム、投映像表示用の合わせガラス、および、画像表示システム
WO2019163969A1 (ja) 2018-02-23 2019-08-29 富士フイルム株式会社 画像表示用合わせガラスの製造方法、画像表示用合わせガラス、および、画像表示システム
WO2019188846A1 (ja) 2018-03-29 2019-10-03 富士フイルム株式会社 画像形成方法
WO2020008961A1 (ja) 2018-07-02 2020-01-09 富士フイルム株式会社 加飾フィルム、加飾方法、加飾成型体の製造方法、及び、加飾成型フィルム
WO2020080355A1 (ja) 2018-10-17 2020-04-23 富士フイルム株式会社 投映像表示用部材、ウインドシールドガラスおよびヘッドアップディスプレイシステム
WO2020122023A1 (ja) 2018-12-10 2020-06-18 富士フイルム株式会社 投映像表示用部材、ウインドシールドガラスおよびヘッドアップディスプレイシステム
WO2020179787A1 (ja) 2019-03-06 2020-09-10 富士フイルム株式会社 投映像表示用積層フィルム、投映像表示用の合わせガラス、および、画像表示システム
WO2020194831A1 (ja) 2019-03-28 2020-10-01 富士フイルム株式会社 インクジェット記録用インクセット及び画像記録方法
US12158655B2 (en) 2019-03-28 2024-12-03 Nippon Kayaku Kabushiki Kaisha Optical film and eyewear
WO2020262474A1 (ja) 2019-06-27 2020-12-30 富士フイルム株式会社 成型用加飾フィルム、成型物、及びディスプレイ
WO2021059879A1 (ja) 2019-09-27 2021-04-01 富士フイルム株式会社 画像記録方法
WO2021060402A1 (ja) 2019-09-27 2021-04-01 富士フイルム株式会社 ヘッドアップディスプレイ用プロジェクター
WO2021200655A1 (ja) 2020-03-30 2021-10-07 富士フイルム株式会社 反射フィルム、ウインドシールドガラスおよびヘッドアップディスプレイシステム
WO2021220794A1 (ja) 2020-04-28 2021-11-04 富士フイルム株式会社 化合物、液晶組成物、硬化物およびフィルム
WO2021246402A1 (ja) 2020-06-03 2021-12-09 富士フイルム株式会社 反射フィルム、合わせガラスの製造方法、および、合わせガラス
WO2022075184A1 (ja) 2020-10-09 2022-04-14 富士フイルム株式会社 反射フィルム、ウインドシールドガラス、および、ヘッドアップディスプレイシステム
WO2022123946A1 (ja) 2020-12-09 2022-06-16 富士フイルム株式会社 反射フィルム、ウインドシールドガラスおよびヘッドアップディスプレイシステム
WO2022138142A1 (ja) 2020-12-25 2022-06-30 富士フイルム株式会社 画像記録方法及びインクジェット記録物
WO2023054324A1 (ja) 2021-09-30 2023-04-06 富士フイルム株式会社 ヘッドアップディスプレイシステム及び輸送機
WO2023080115A1 (ja) 2021-11-05 2023-05-11 富士フイルム株式会社 虚像表示装置、ヘッドアップディスプレイシステム及び輸送機
WO2023085370A1 (ja) 2021-11-12 2023-05-19 富士フイルム株式会社 画像記録物及び画像記録方法
WO2023200018A1 (ja) 2022-04-15 2023-10-19 富士フイルム株式会社 反射フィルム、積層体、ウインドシールドガラス、画像表示システム
WO2023248719A1 (ja) 2022-06-21 2023-12-28 富士フイルム株式会社 画像記録物及び画像記録物の製造方法、並びに、加飾成形体
WO2024106459A1 (ja) 2022-11-17 2024-05-23 富士フイルム株式会社 投映像表示用積層フィルム、投映像表示用合わせガラス、投映像表示システム
EP4621474A1 (en) 2022-11-17 2025-09-24 FUJIFILM Corporation Laminated film for projected-image display, laminated glass for projected-image display, and projected-image display system
WO2025013896A1 (ja) 2023-07-11 2025-01-16 富士フイルム株式会社 組成物、光学異方性層、硬化膜、回折素子
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
WO2025018426A1 (ja) 2023-07-20 2025-01-23 富士フイルム株式会社 コレステリック液晶層の製造方法、コレステリック液晶層、反射フィルム、合わせガラス、ヘッドアップディスプレイシステム、組成物

Also Published As

Publication number Publication date
DE69820612T2 (de) 2004-10-14
JP2001527570A (ja) 2001-12-25
EP0983225A1 (en) 2000-03-08
HK1026195A1 (en) 2000-12-08
EP0983225B1 (en) 2003-12-17
KR100566684B1 (ko) 2006-04-03
CN1257473A (zh) 2000-06-21
AU7227698A (en) 1998-12-11
US6395351B1 (en) 2002-05-28
CN1213989C (zh) 2005-08-10
DE69820612D1 (de) 2004-01-29
KR20010012775A (ko) 2001-02-26

Similar Documents

Publication Publication Date Title
EP0983225B1 (en) New polymerisable liquid crystalline compounds
EP1100766B1 (en) Crosslinkable liquid crystalline compounds
EP1187802B1 (en) Liquid crystal compounds
EP1169293B1 (en) Liquid crystal compounds
JPH08104870A (ja) 光重合性液晶
JPH07501850A (ja) 液晶性素材
WO2000004110A1 (en) Compositions
EP1102741B1 (en) Liquid crystalline compounds
EP1046631A1 (en) Liquid crystalline compounds
US5417882A (en) Liquid-crystalline compounds
HK1026195B (en) New polymerisable liquid crystalline compounds
US5417884A (en) Defined oligomeric liquid-crystalline compounds having smectic liquid-crystalline phases
Lub et al. The synthesis of liquid‐crystalline diacrylates derived from cyclohexane units
JPH0393748A (ja) 光学活性化合物および液晶組成物
EP0496896B1 (en) Cyclobutanecarboxylic acid derivative and liquid crystal composition containing the same
HK1011014A1 (en) Photocrosslinkable liquid crystalline 1,2-phenylene derivatives
HK1011014B (en) Photocrosslinkable liquid crystalline 1,2-phenylene derivatives
HK1011042B (en) Photo-curable liquid crystals
HK1033755B (en) Liquid crystalline compounds
HK1011042A1 (en) Photo-curable liquid crystals

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 98805335.7

Country of ref document: CN

AK Designated states

Kind code of ref document: A1

Designated state(s): AL AM AT AU AZ BA BB BG BR BY CA CH CN CU CZ DE DK EE ES FI GB GE GH GM GW HU ID IL IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT UA UG US UZ VN YU ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW SD SZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN ML MR NE SN TD TG

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 1998919404

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 09443214

Country of ref document: US

Ref document number: 1019997010737

Country of ref document: KR

ENP Entry into the national phase

Ref document number: 1998 550182

Country of ref document: JP

Kind code of ref document: A

WWP Wipo information: published in national office

Ref document number: 1998919404

Country of ref document: EP

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

WWP Wipo information: published in national office

Ref document number: 1019997010737

Country of ref document: KR

WWG Wipo information: grant in national office

Ref document number: 1998919404

Country of ref document: EP

WWG Wipo information: grant in national office

Ref document number: 1019997010737

Country of ref document: KR