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WO2015030004A1 - Composition formant un film durci, matériau d'alignement et matériau de déphasage - Google Patents

Composition formant un film durci, matériau d'alignement et matériau de déphasage Download PDF

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Publication number
WO2015030004A1
WO2015030004A1 PCT/JP2014/072320 JP2014072320W WO2015030004A1 WO 2015030004 A1 WO2015030004 A1 WO 2015030004A1 JP 2014072320 W JP2014072320 W JP 2014072320W WO 2015030004 A1 WO2015030004 A1 WO 2015030004A1
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Prior art keywords
group
carbon atoms
fluorine
cured film
alkyl group
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PCT/JP2014/072320
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English (en)
Japanese (ja)
Inventor
真 畑中
大村　浩之
耕平 後藤
裕太 菅野
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Nissan Chemical Corp
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Nissan Chemical Corp
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Priority to JP2015534237A priority Critical patent/JP6460340B2/ja
Priority to CN201480046361.8A priority patent/CN105474083B/zh
Priority to KR1020167005250A priority patent/KR102193060B1/ko
Publication of WO2015030004A1 publication Critical patent/WO2015030004A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G02B5/3016—Polarising elements involving passive liquid crystal elements

Definitions

  • the present invention relates to a cured film forming composition suitable for a vertical alignment material for vertically aligning liquid crystal molecules.
  • the present invention relates to a liquid crystal display device (LCD), specifically, an IPS liquid crystal display device (In-plane Switching LCD) filled with liquid crystal having positive dielectric anisotropy ( ⁇ > 0);
  • the present invention relates to a cured film forming composition, an alignment material, and a retardation material, which are useful for producing a + C plate (positive C plate) used for improving the viewing angle characteristics of in-plane alignment switching LCD).
  • IPS-LCD is characterized by little change in brightness / color due to viewing angle because no vertical tilt of liquid crystal molecules occurs. However, it is difficult to increase contrast ratio, brightness, and response speed. It is done.
  • a viewing angle compensation film is not used in the early IPS-LCD, and an IPS-LCD not using such a viewing angle compensation film has a tilt angle of Due to the relatively large light leakage in the dark state, there is a disadvantage of showing a low contrast ratio value.
  • Patent Document 2 discloses an IPS-LCD compensation film using a + C plate and a + A plate (positive A plate).
  • This document shows the following configuration of the liquid crystal display element described therein. 1) A liquid crystal layer having a horizontal alignment is sandwiched between both substrates supplied by electrodes capable of applying an electric field parallel to the surface of the liquid crystal layer. 2) One or more + A plates and + C plates are sandwiched between both polarizing plates. 3) The main optical axis of the + A plate is perpendicular to the main optical axis of the liquid crystal layer. 4) of the liquid crystal layer retardation value R LC, + C plate retardation value R + C, + A retardation value R + A plate is determined so as to satisfy the following equation.
  • the + A plate is intended to provide an IPS-LCD having high contrast characteristics at the front and tilt angles and low color shift by minimizing dark light leakage at the tilt angle.
  • an IPS-LCD having a + C plate is disclosed (Patent Document 3).
  • JP-A-2-256603 Japanese Patent Laid-Open No. 11-133408 JP 2009-122715 A JP 2001-281669 A
  • the + C plate is very useful as an optical compensation film for IPS-LCD because it can compensate for light leakage where the viewing angle of the polarizing plate is large.
  • a conventionally proposed vertical alignment film using polyimide needs to use a polyimide solvent such as N-methyl-2-pyrrolidone for film formation. For this reason, although it does not become a problem in a glass base material, when a base material is a film, there exists a problem of giving a damage to a base material at the time of alignment film formation.
  • the vertical alignment film using polyimide requires firing at a high temperature, and there is a problem that the film substrate cannot withstand the high temperature.
  • a method for forming a vertical alignment film by directly treating a substrate with a silane coupling agent having a long-chain alkyl or the like has also been proposed, but when a hydroxy group does not exist on the substrate surface, There exists a problem that a process is difficult and a base material is restrict
  • An object of the present invention is to provide a cured film forming composition for providing an alignment material capable of stably aligning a polymerizable liquid crystal vertically under low-temperature and short-time firing conditions even on a resin film.
  • Another object of the present invention is obtained from the above cured film-forming composition, having excellent vertical alignment, and stably aligning a polymerizable liquid crystal vertically on a resin film under low-temperature and short-time firing conditions. It is an object to provide a phase difference material useful for an alignment material that can be used and a + C plate formed using the alignment material.
  • the present inventors have made extensive studies and, as a result, by selecting a cured film forming material based on an acrylic copolymer having a long-chain alkyl group in the side chain, The present inventors have found that a cured film having excellent vertical alignment can be formed regardless of the present invention, and completed the present invention.
  • the present invention as a first aspect, (A) a polymer obtained by reacting a carboxyl group of a compound having a carboxyl group and a vertical alignment group with an epoxy group of a polymer having one or more epoxy groups in the side chain or terminal, and (B) a crosslinking agent and ( C) A cured film-forming composition containing at least one compound selected from the group consisting of acid catalysts,
  • the vertical alignment group is a group represented by the following formula (1), and relates to a cured film forming composition.
  • Y 1 represents a single bond
  • Y 2 represents a single bond or an alkylene group having 1 to 15 carbon atoms, or a divalent cyclic group selected from a benzene ring, a cyclohexane ring or a heterocyclic ring, and any hydrogen atom on the cyclic group is a carbon Substituted with an alkyl group having 1 to 3 atoms, an alkoxyl group having 1 to 3 carbon atoms, a fluorine-containing alkyl group having 1 to 3 carbon atoms, a fluorine-containing alkoxyl group having 1 to 3 carbon atoms, or a fluorine atom.
  • Y 3 represents a single bond or an alkylene group having 1 to 15 carbon atoms
  • Y 4 represents a single bond, a divalent cyclic group selected from a benzene ring, a cyclohexane ring or a heterocyclic ring, or a divalent organic group having 17 to 30 carbon atoms and having a steroid skeleton.
  • Arbitrary hydrogen atoms on the group are alkyl groups having 1 to 3 carbon atoms, alkoxyl groups having 1 to 3 carbon atoms, fluorine-containing alkyl groups having 1 to 3 carbon atoms, fluorine containing 1 to 3 carbon atoms May be substituted with an alkoxyl group or a fluorine atom
  • Y 5 represents a divalent cyclic group selected from a benzene ring, a cyclohexane ring or a heterocyclic ring, and any hydrogen atom on these cyclic groups is an alkyl group having 1 to 3 carbon atoms, or 1 to 3 carbon atoms.
  • the alkylene group as Y 2 and Y 3 and the substituent on the cyclic group or the alkyl group, fluorine-containing alkyl group, alkoxyl group and fluorine-containing alkoxy group as Y 6 are linear, branched or cyclic. Any or a combination thereof, Also, the alkylene group as Y 2 and Y 3 , and the alkyl group, fluorine-containing alkyl group, alkoxyl group and fluorine-containing alkoxy group as Y 6 are interrupted by 1 to 3 bonding groups unless the bonding groups are adjacent to each other.
  • Y 2 , Y 4 or Y 5 represents a divalent cyclic group
  • Y 4 represents a divalent organic group having a steroid skeleton
  • Y 2 or Y 3 represents an alkylene group
  • Y 6 Represents an alkyl group or a fluorine-containing alkyl group, the divalent cyclic group, the divalent organic group having the steroid skeleton, the alkylene group, the alkyl group and the fluorine-containing alkyl group are groups adjacent to them.
  • the bonding group includes —O—, —CH 2 O—, —CO—, —COO—, —OCO—, —NHCO—, —CONH—, —NH—CO—O—, —O—CO—NH.
  • the total number of carbon atoms of the fluorine-containing alkyl group having 1 to 18 carbon atoms, the alkoxyl group having 1 to 18 carbon atoms and the fluorine-containing alkoxyl group having 1 to 18 carbon atoms is 6 to 30).
  • the cured film formation according to the first aspect, wherein the polymer having one or more epoxy groups in the side chain or terminal is a polymer having a ring structure in the main chain and having a number average molecular weight of 300 to 20,000. Relates to the composition.
  • the polymer having one or more epoxy groups in the side chain or the terminal is bisphenol A type epoxy resin, bisphenol F epoxy resin, phenol novolac type epoxy resin, cresol novolac type epoxy resin, bisphenol A novolak type epoxy resin.
  • a cured film-forming composition according to the first aspect or the second aspect which is any one polymer selected from the group consisting of 1,2-epoxy-4- (2-oxiranyl) cyclohexane adduct of polyol and .
  • the cured film formation composition as described in any one of the 1st viewpoint thru
  • the cured film formation according to any one of the first aspect to the fourth aspect containing 1 part by mass to 100 parts by mass of the component (B) based on 100 parts by mass of the component (A) Relates to the composition.
  • the curing according to any one of the first to fifth aspects containing 0.01 to 20 parts by mass of component (C)
  • the present invention relates to a film-forming composition.
  • the present invention relates to an alignment material obtained by curing the cured film forming composition according to any one of the first aspect to the sixth aspect.
  • the present invention relates to a retardation material characterized by being formed using a cured film obtained from the cured film forming composition according to any one of the first aspect to the sixth aspect.
  • the first aspect of the present invention in order to provide an alignment material that has excellent vertical alignment and can stably align a polymerizable liquid crystal vertically under low-temperature and short-time firing conditions even on a resin film.
  • Useful cured film forming compositions can be provided.
  • the second aspect of the present invention it is possible to provide an alignment material that has excellent vertical alignment and can stably align the polymerizable liquid crystal vertically under low-temperature and short-time firing conditions.
  • a retardation material that can be formed on a resin film with high efficiency, is highly transparent, and has high solvent resistance can be provided.
  • the carboxyl group of the compound having a carboxyl group and a vertical alignment group is added to the epoxy group of the polymer having one or more epoxy groups in the side chain or terminal as the component (A). It contains at least one compound selected from the group consisting of a reacted polymer, a crosslinking agent as component (B) and an acid catalyst as component (C).
  • the cured film forming composition of the present invention can contain other additives in addition to the above components (A), (B), and (C) as long as the effects of the present invention are not impaired.
  • details of each component will be described.
  • the component (A) contained in the cured film forming composition of the present invention is a carboxyl of a compound having a carboxyl group and a vertical alignment group with respect to an epoxy group of a polymer having one or more epoxy groups in the side chain or terminal. It is a polymer that has been reacted with a group.
  • the polymer of component (A) is also referred to as “vertical alignment polymer”.
  • a polymer having one or more epoxy groups in the side chain or terminal can be produced by addition polymerization using an addition polymerizable monomer having an epoxy group.
  • the polymer which has 1 or more of epoxy groups in a side chain or the terminal can be manufactured by reaction of the high molecular compound which has a hydroxy acid group, and the compound which has epoxy groups, such as epichlorohydrin and glycidyl tosylate.
  • polystyrene resin examples include, for example, polyglycidyl methacrylate, glycidyl methacrylate copolymer, poly (3,4-epoxycyclohexylmethyl methacrylate), and 3,4-epoxycyclohexylmethyl methacrylate.
  • Copolymer Bisphenol A type epoxy resin, bisphenol F epoxy resin, phenol novolac type epoxy resin, cresol novolac type epoxy resin, bisphenol A novolak type epoxy resin, 1,2-epoxy-4- (2-oxiranyl) cyclohexane adduct of trimethylolpropane Etc.
  • a polymer having a ring structure in the main chain is preferable.
  • bisphenol A type epoxy resin, bisphenol F epoxy resin, phenol novolac type epoxy resin, A cresol novolac type epoxy resin, a bisphenol A novolak type epoxy resin, a 1,2-epoxy-4- (2-oxiranyl) cyclohexane adduct of polyol and the like are preferable from the viewpoint of improving the liquid crystal coating property.
  • the molecular weight of the polymer having one or more of these epoxy groups in the side chain or terminal is preferably a polystyrene-equivalent number average molecular weight (hereinafter referred to as a number average molecular weight) of 300 to 20,000. It is preferably 400 to 10,000, more preferably 500 to 8,000.
  • the polymer having one or more epoxy groups in the side chain or terminal a commercially available product can be suitably used.
  • the bisphenol A type epoxy resin include jER1001, 1002, 1003, 1004, and 1004. 1055, 1007, 1009, 1010, 834, 828 (Mitsubishi Chemical Corporation) and the like, and bisphenol F type epoxy resin is jER806, 807 (Mitsubishi Chemical Corporation) ) And the like as phenol novolac type epoxy resins, jER152, 154 (above, manufactured by Mitsubishi Chemical Corporation), EPPN201, 202 (above, manufactured by Nippon Kayaku Co., Ltd.), etc., and cresol novolac type epoxy resins.
  • ECN-1299 (manufactured by Asahi Kasei Corporation), EOCN-102, EOCN-103S, EOCN- 04S, EOCN-1020, EOCN-1025, EOCN-1027 (manufactured by Nippon Kayaku Co., Ltd.), jER80S75 (manufactured by Mitsubishi Chemical Corporation), etc., and jER157S70 (Mitsubishi Chemical)
  • EHPE-3150 manufactured by Daicel Corporation
  • Daicel Corporation Daicel Corporation
  • the vertical alignment group refers to a group containing a hydrocarbon group having, for example, about 6 to 20 carbon atoms, and specifically refers to a group represented by the formula [1] described later.
  • the compound having a carboxyl group and a vertical alignment group include a compound having a carboxyl group and a hydrocarbon group having about 6 to 20 carbon atoms.
  • the hydrocarbon group having 6 to 20 carbon atoms include linear, branched or cyclic alkyl groups having 6 to 20 carbon atoms or hydrocarbon groups having 6 to 20 carbon atoms including an aromatic group. .
  • the vertical alignment group is a group represented by the following formula [1].
  • Y 1 represents a single bond.
  • Y 2 represents a single bond or an alkylene group having 1 to 15 carbon atoms.
  • Examples of Y 2 include a divalent cyclic group selected from a benzene ring, a cyclohexane ring, and a heterocyclic ring.
  • An arbitrary hydrogen atom on these cyclic groups is an alkyl group having 1 to 3 carbon atoms, a carbon atom number of 1 A pyrrole ring, an imidazole ring, an alkyl group having 1 to 3 carbon atoms, a fluorine-containing alkyl group having 1 to 3 carbon atoms, a fluorine-containing alkoxyl group having 1 to 3 carbon atoms or a fluorine atom that may be substituted with a fluorine atom.
  • Examples of the alkyl group exemplified as the substituent include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and a cyclopropyl group.
  • examples of the alkyl group include oxygen groups. And a group to which an atom —O— is bonded.
  • Examples of the fluorine-containing alkyl group and fluorine-containing alkoxyl group include groups in which any hydrogen atom of the alkyl group and alkoxyl group is substituted with a fluorine atom.
  • Y 2 is preferably a benzene ring or a cyclohexane ring from the viewpoint of ease of synthesis.
  • Y 3 represents a single bond or an alkylene group having 1 to 15 carbon atoms.
  • Y 4 represents a single bond or a divalent cyclic group selected from a benzene ring, a cyclohexane ring or a heterocyclic ring, and any hydrogen atom on these cyclic groups has 1 carbon atom. It may be substituted with an alkyl group having 3 to 3, an alkoxyl group having 1 to 3 carbon atoms, a fluorine-containing alkyl group having 1 to 3 carbon atoms, a fluorine-containing alkoxyl group having 1 to 3 carbon atoms, or a fluorine atom.
  • the alkyl group and the like mentioned as the heterocyclic ring and the substituent can be the same as those mentioned for Y 2 above.
  • Y 4 may be a divalent organic group selected from organic groups having 17 to 30 carbon atoms and having a steroid skeleton.
  • Preferred examples thereof include cholesteryl, androsteryl, ⁇ -cholesteryl, epiandrosteryl, erygosteryl, estril, 11 ⁇ -hydroxymethylsteryl, 11 ⁇ -progesteryl, lanosteryl, melatranyl, methyltestosteryl, noretisteryl, pregnenoyl, ⁇ -sitosteryl, It is a divalent group having a structure in which two hydrogen atoms are removed from a structure selected from stigmasteryl, testosteryl, acetic acid cholesterol ester, and the like. More specifically, for example, as follows.
  • Y 4 is preferably a benzene ring, a cyclohexane ring, or a divalent organic group having 17 to 30 carbon atoms and having a steroid skeleton from the viewpoint of ease of synthesis.
  • Y 5 represents a divalent cyclic group selected from a benzene ring, a cyclohexane ring or a heterocyclic ring, and an arbitrary hydrogen atom on these cyclic groups is an alkyl group having 1 to 3 carbon atoms, It may be substituted with an alkoxyl group having 1 to 3 carbon atoms, a fluorine-containing alkyl group having 1 to 3 carbon atoms, a fluorine-containing alkoxyl group having 1 to 3 carbon atoms, or a fluorine atom.
  • the alkyl group and the like mentioned as the heterocyclic ring and the substituent can be the same as those mentioned above for Y 4 .
  • Y 5 is preferably a benzene ring or a cyclohexane ring.
  • n represents an integer of 0 to 4, and when n is 2 or more, Y 5 may be the same group or different groups.
  • n is preferably 0 to 3 from the viewpoint of availability of raw materials and ease of synthesis. More preferred is 0-2.
  • Y 6 represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, a fluorine-containing alkyl group having 1 to 18 carbon atoms, an alkoxyl group having 1 to 18 carbon atoms, or 1 to 18 carbon atoms. Represents a fluorine-containing alkoxyl group.
  • Y 6 is an alkyl group having 1 to 18 carbon atoms, a fluorine-containing alkyl group having 1 to 10 carbon atoms, an alkoxyl group having 1 to 18 carbon atoms, or a fluorine-containing alkoxyl group having 1 to 10 carbon atoms.
  • Y 6 is an alkyl group having 1 to 12 carbon atoms or an alkoxyl group having 1 to 12 carbon atoms. Particularly preferably, Y 6 is an alkyl group having 1 to 9 carbon atoms or an alkoxyl group having 1 to 9 carbon atoms.
  • Y 4 is a divalent organic group having a steroid skeleton
  • Y 6 is preferably a hydrogen atom.
  • the alkylene group, alkyl group, fluorine-containing alkyl group, alkoxyl group or fluorine-containing alkoxy group mentioned in the definition in the above formula [1] is any one of linear, branched, cyclic, or a combination thereof. Also good.
  • the alkyl group is, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, 1-methyl-n.
  • the bivalent group which removed one arbitrary hydrogen atom from the said alkyl group can be mentioned.
  • the alkoxyl group include groups in which an oxygen atom —O— is bonded to the groups listed as specific examples of the alkyl group.
  • the fluorine-containing alkyl group and fluorine-containing alkoxyl group include groups in which any hydrogen atom of the alkyl group and alkoxyl group is substituted with a fluorine atom.
  • the alkylene group as Y 2 and Y 3 and the substituent on the cyclic group or the alkyl group, fluorine-containing alkyl group, alkoxyl group and fluorine-containing alkoxy group as Y 6 are linear, branched, or cyclic. Or any combination thereof. Further, the alkylene group as Y 2 and Y 3 , and the alkyl group, fluorine-containing alkyl group, alkoxyl group and fluorine-containing alkoxy group as Y 6 are 1 to 3 bonding groups as long as the bonding groups are not adjacent to each other. It may be interrupted.
  • Y 2 , Y 4 or Y 5 represents a divalent cyclic group
  • Y 4 represents a divalent organic group having a steroid skeleton
  • Y 2 or Y 3 represents an alkylene group
  • Y represents an alkyl group or a fluorine-containing alkyl group
  • the alkyl group and the fluorine-containing alkyl group may be bonded to a group adjacent thereto via a bonding group.
  • the linking group includes —O—, —CH 2 O—, —CO—, —COO—, —OCO—, —NHCO—, —CONH—, —NH—CO—O—, —O—CO—NH.
  • each of Y 2 to Y 6 represents an alkylene group having 1 to 15 carbon atoms, a benzene ring, a cyclohexane ring, a heterocyclic ring, a divalent organic group having a steroid skeleton, or an alkyl group having 1 to 18 carbon atoms.
  • the total number of carbon atoms of the fluorine-containing alkyl group having 1 to 18 carbon atoms, the alkoxyl group having 1 to 18 carbon atoms and the fluorine-containing alkoxyl group having 1 to 18 carbon atoms is 6 to 30, for example 6 to 20.
  • the vertical alignment group is preferably a group containing an alkyl group having 7 to 18 carbon atoms, particularly 8 to 15 carbon atoms.
  • the compound having a carboxyl group and a vertical alignment group is a compound in which a carboxyl group is bonded to the vertical alignment group.
  • the vertical alignment polymer of component (A) in the present invention reacts with the carboxyl group of the compound having a carboxyl group and a vertical alignment group with respect to the epoxy group of the polymer having one or more epoxy groups in the side chain or terminal. Polymer. When the epoxy group reacts with the carboxyl group, a bond of —CH 2 —CH (OH) —CH 2 — is generated.
  • the amount of the polymer having one or more epoxy groups in the side chain or terminal and the compound having a carboxyl group and a vertically aligning group to obtain the above vertically aligned polymer is one or more in the side chain or terminal. It is preferable to use the compound having a carboxyl group and a vertical alignment group in an amount of 5 to 60 equivalents with respect to 1 equivalent of the epoxy of the polymer. When the carboxyl group of the compound having a carboxyl group and a vertically aligning group is less than 5 equivalents relative to 1 equivalent of the epoxy having 1 or more epoxy groups in the side chain or terminal, the desired vertically aligned polymer is In some cases, sufficient vertical alignment cannot be obtained.
  • the amount of the carboxyl group with respect to 1 equivalent of the epoxy of the polymer having one or more epoxy groups in the side chain or the terminal does not contain the carboxyl group of the compound having the carboxyl group and the vertical alignment group, and the vertical alignment group.
  • the total amount of carboxyl groups of the compound having a carboxyl group is preferably 5 to 60 equivalents.
  • the procedure for obtaining the vertical alignment polymer used in the present invention is not particularly limited.
  • a polymer having one or more epoxy groups in the side chain or terminal, a compound having a carboxyl group and a vertical alignment group, and optionally a vertical alignment group can be obtained by reacting a compound having no carboxyl group and having a carboxyl group in a solvent coexisting with a reaction catalyst or the like at a temperature of 50 to 150 ° C.
  • the solvent to be used is not particularly limited as long as it dissolves a polymer having one or more epoxy groups in the side chain or terminal, a compound having a carboxyl group and a vertical alignment group, a polymerization initiator, and the like.
  • Reaction catalysts include benzyltrimethylammonium chloride, benzyltrimethylammonium bromide, benzyltriethylammonium chloride, benzyltriethylammonium bromide, benzyltripropylammonium chloride, benzyltripropylammonium bromide, tetramethylammonium chloride, tetraethylammonium bromide, tetrapropylammonium chloride.
  • Quaternary ammonium salts such as tetrapropylammonium bromide; quaternary compounds such as tetraphenylphosphonium chloride, tetraphenylphosphonium bromide, benzyltriphenylphosphonium chloride, benzyltriphenylphosphonium bromide, ethyltriphenylphosphonium chloride, ethyltriphenylphosphonium bromide Or the like can be mentioned Suhon'niumu salt.
  • the vertically aligned polymer obtained by the above method is usually in the form of a solution dissolved in a solvent. As will be described later, the obtained vertically aligned polymer solution can be used as it is as the component (A).
  • the vertically aligned polymer solution obtained by the above method is poured into diethyl ether or water under stirring to cause reprecipitation, and the generated precipitate is filtered and washed, and then at normal or reduced pressure at room temperature. It can be dried or heat-dried to obtain a vertically oriented polymer powder.
  • the reaction catalyst coexisting with the vertically aligned polymer and the unreacted compound can be removed, and as a result, a purified vertically aligned polymer powder is obtained. If sufficient purification cannot be achieved by a single operation, the obtained powder may be redissolved in a solvent and the above operation may be repeated.
  • the vertically aligned polymer may be used in the form of a powder or in the form of a solution obtained by re-dissolving the purified powder in a solvent described later.
  • the vertical alignment polymer of component (A) may be a mixture of a plurality of types of vertical alignment polymers.
  • Component (B) in the cured film forming composition of the present invention is a crosslinking agent.
  • the crosslinking agent as the component (B) is preferably a crosslinking agent having a group that forms a crosslinking with the thermally crosslinkable functional group of the component (A), such as a methylol group or an alkoxymethyl group.
  • Examples of the compound having these groups include methylol compounds such as alkoxymethylated glycoluril, alkoxymethylated benzoguanamine, and alkoxymethylated melamine.
  • alkoxymethylated glycoluril examples include, for example, 1,3,4,6-tetrakis (methoxymethyl) glycoluril, 1,3,4,6-tetrakis (butoxymethyl) glycoluril, 1,3,4 , 6-tetrakis (hydroxymethyl) glycoluril, 1,3-bis (hydroxymethyl) urea, 1,1,3,3-tetrakis (butoxymethyl) urea, 1,1,3,3-tetrakis (methoxymethyl) Examples include urea, 1,3-bis (hydroxymethyl) -4,5-dihydroxy-2-imidazolinone, and 1,3-bis (methoxymethyl) -4,5-dimethoxy-2-imidazolinone.
  • glycoluril compounds (trade names: Cymel (registered trademark) 1170, Powderlink (registered trademark) 1174) manufactured by Nippon Cytec Industries Co., Ltd. (former Mitsui Cytec Co., Ltd.), methylated urea resins (Trade name: UFR (registered trademark) 65), butylated urea resin (trade names: UFR (registered trademark) 300, U-VAN10S60, U-VAN10R, U-VAN11HV), DIC Corporation (formerly Dainippon Ink Chemical Co., Ltd.) Urea / formaldehyde resin (high condensation type, trade name: Beccamin (registered trademark) J-300S, P-955, N) manufactured by Kogyo Co., Ltd.).
  • alkoxymethylated benzoguanamine examples include tetramethoxymethylbenzoguanamine.
  • Commercially available products are made by Nippon Cytec Industries Co., Ltd. (formerly Mitsui Cytec Co., Ltd.) (trade name: Cymel (registered trademark) 1123), manufactured by Sanwa Chemical Co., Ltd. (product name: Nicarak (registered trademark) BX-) 4000, BX-37, BL-60, BX-55H) and the like.
  • alkoxymethylated melamine examples include, for example, hexamethoxymethylmelamine.
  • methoxymethyl type melamine compounds (trade names: Cymel (registered trademark) 300, 301, 303, 350) manufactured by Nippon Cytec Industries Co., Ltd. (former Mitsui Cytec Co., Ltd.), butoxymethyl type melamine Compound (trade name: My Coat (registered trademark) 506, 508), methoxymethyl type melamine compound (trade name: Nicalac (registered trademark) MW-30, MW-22, MW-) manufactured by Sanwa Chemical Co., Ltd. 11, MS-001, MX-002, MX-730, MX-750, MX-035), butoxymethyl type melamine compound (trade name: Nicalac (registered trademark) MX-45, MX-410) , MX-302).
  • a compound obtained by condensing a melamine compound, urea compound, glycoluril compound and benzoguanamine compound in which the hydrogen atom of the amino group is substituted with a methylol group or an alkoxymethyl group may be used.
  • the high molecular weight compound manufactured from the melamine compound and the benzoguanamine compound which are described in US Patent 6,323,310 is mentioned.
  • Examples of commercially available products of the melamine compound include trade name: Cymel (registered trademark) 303 and the like.
  • Examples of commercially available products of the benzoguanamine compound include product name: Cymel (registered trademark) 1123 (Nippon Cytec Industries, Ltd.). ) (Formerly Mitsui Cytec Co., Ltd.).
  • hydroxymethyl groups that is, methylol groups
  • alkoxymethyl groups such as N-hydroxymethylacrylamide, N-methoxymethylmethacrylamide, N-ethoxymethylacrylamide, N-butoxymethylmethacrylamide, etc.
  • Polymers produced using an acrylamide compound or a methacrylamide compound substituted with a can also be used.
  • Examples of such a polymer include poly (N-butoxymethylacrylamide), a copolymer of N-butoxymethylacrylamide and styrene, a copolymer of N-hydroxymethylmethacrylamide and methylmethacrylate, and N-ethoxymethyl.
  • Examples thereof include a copolymer of methacrylamide and benzyl methacrylate, and a copolymer of N-butoxymethylacrylamide, benzyl methacrylate and 2-hydroxypropyl methacrylate.
  • the weight average molecular weight (polystyrene equivalent value) of such a polymer is 1,000 to 500,000, preferably 2,000 to 200,000, more preferably 3,000 to 150,000. More preferably, it is 3,000 to 50,000.
  • cross-linking agents can be used alone or in combination of two or more.
  • the content of the crosslinking agent as the component (B) is preferably 1 part by mass to 100 parts by mass, more preferably based on 100 parts by mass of the compound (A). 5 parts by weight to 80 parts by weight.
  • content of a crosslinking agent is too small, the solvent tolerance of the cured film obtained from a cured film formation composition will fall, and vertical orientation will fall. On the other hand, when the content is excessive, the vertical alignment property and the storage stability may be lowered.
  • the component (C) in the cured film forming composition of the present invention is an acid catalyst.
  • an acid catalyst which is (C) component an acid or a thermal acid generator can be used conveniently, for example.
  • This component (C) is effective in promoting the thermosetting reaction of the cured film forming composition of the present invention.
  • Specific examples of the component (C) include sulfonic acid group-containing compounds, hydrochloric acid or salts thereof as the acid.
  • the thermal acid generator is not particularly limited as long as it is a compound that thermally decomposes during heat treatment to generate an acid, that is, a compound that thermally decomposes at a temperature of 80 ° C. to 250 ° C. to generate an acid. .
  • the acid include, for example, hydrochloric acid or a salt thereof; methanesulfonic acid, ethanesulfonic acid, propanesulfonic acid, butanesulfonic acid, pentanesulfonic acid, octanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, camphor Sulfonic acid, trifluoromethanesulfonic acid, p-phenolsulfonic acid, 2-naphthalenesulfonic acid, mesitylenesulfonic acid, p-xylene-2-sulfonic acid, m-xylene-2-sulfonic acid, 4-ethylbenzenesulfonic acid, 1H, 1H, 2H, 2H-perfluorooctanesulfonic acid, perfluoro (2-ethoxyethane) sulfonic acid, pentafluoroethanesulfonic acid, non
  • Examples of the compound that generates an acid by heat include, for example, bis (tosyloxy) ethane, bis (tosyloxy) propane, bis (tosyloxy) butane, p-nitrobenzyl tosylate, o-nitrobenzyl tosylate, 1,2,3 -Phenylenetris (methyl sulfonate), p-toluenesulfonic acid pyridinium salt, p-toluenesulfonic acid morphonium salt, p-toluenesulfonic acid ethyl ester, p-toluenesulfonic acid propyl ester, p-toluenesulfonic acid butyl ester, p- Toluenesulfonic acid isobutyl ester, p-toluenesulfonic acid methyl ester, p-toluenesulfonic acid phenethyl ester,
  • the content of the component (C) in the cured film forming composition of the present invention is preferably 0.01 to 20 parts by mass, more preferably 0.1 parts by mass with respect to 100 parts by mass of the component (A) compound. Part to 15 parts by weight, more preferably 0.5 part to 10 parts by weight.
  • the content of the component (C) is preferably 0.01 to 20 parts by mass or more, sufficient thermosetting and solvent resistance can be imparted. However, when it is more than 20 parts by mass, the storage stability of the composition may be lowered.
  • the cured film forming composition of the present invention is mainly used in a solution state dissolved in a solvent.
  • the solvent used in that case is only required to be able to dissolve the component (A), the component (B) and / or the component (C), and other additives which can be optionally added, and the type and structure thereof are particularly limited. It is not something.
  • the solvent include, for example, methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, 2-methyl-1-butanol, n-pentanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, Methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether, propylene glycol propyl ether, propylene glycol propyl ether acetate, Toluene, xylene, methyl Ethyl ketone, isobutyl methyl ketone, cyclopentanone, cyclohexanone, 2-butanone
  • the cured film-forming composition of the present invention is used to produce an alignment material by forming a cured film on a resin film
  • methanol, ethanol, n-propanol, isopropanol, n-butanol, 2-methyl-1-butanol 2-heptanone, isobutyl methyl ketone, diethylene glycol, propylene glycol, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate and the like are preferable from the viewpoint that the resin film is a resistant solvent.
  • solvents can be used alone or in combination of two or more.
  • the cured film-forming composition of the present invention is, as necessary, an adhesion improver, a silane coupling agent, a surfactant, a rheology modifier, a pigment, a dye, a storage stability, as long as the effects of the present invention are not impaired.
  • an adhesion improver e.g., a silane coupling agent, a surfactant, a rheology modifier, a pigment, a dye, a storage stability, as long as the effects of the present invention are not impaired.
  • Agents, antifoaming agents, antioxidants, and the like are examples of the like.
  • the cured film forming composition of the present invention contains (A) a vertically aligned polymer and (B) a cross-linking agent and / or (C) an acid catalyst. It is a composition that can contain other additives as long as they are not impaired. Usually, they are used in the form of a solution in which they are dissolved in a solvent.
  • Preferred examples of the cured film forming composition of the present invention are as follows. [1] A cured film forming composition containing 1 part by mass to 100 parts by mass of the component (B) based on 100 parts by mass of the component (A). [2]: A cured film forming composition containing 1 part by mass to 100 parts by mass of the component (B) and the solvent based on 100 parts by mass of the component (A). [3]: A cured film forming composition containing 0.01 to 20 parts by mass of component (C) and solvent based on 100 parts by mass of component (A). [4]: Based on 100 parts by mass of component (A), cured film formation containing 1 to 100 parts by mass of component (B), 0.01 to 20 parts by mass of component (C), and solvent Composition.
  • the blending ratio, preparation method, and the like when the cured film forming composition of the present invention is used as a solution are described in detail below.
  • the ratio of the solid content in the cured film-forming composition of the present invention is not particularly limited as long as each component is uniformly dissolved in the solvent, but is 1% by mass to 60% by mass, preferably 2%.
  • the mass is from 50% by mass to 50% by mass, and more preferably from 2% by mass to 20% by mass.
  • solid content means what remove
  • the method for preparing the cured film forming composition of the present invention is not particularly limited.
  • a preparation method for example, a method of mixing the component (B) and / or the component (C) in a predetermined ratio with a solution of the component (A) dissolved in a solvent to obtain a uniform solution, or this preparation method In an appropriate stage, there may be mentioned a method in which other additives are further added and mixed as necessary.
  • a vertically aligned polymer solution obtained by a reaction in a solvent can be used as it is.
  • the component (B) and / or the component (C) is added to the solution of the component (A) in the same manner as described above to obtain a uniform solution.
  • a solvent may be further added for the purpose of adjusting the concentration.
  • the solvent used in the production process of the component (A) and the solvent used for adjusting the concentration of the cured film forming composition may be the same or different.
  • the prepared cured film-forming composition solution is preferably used after being filtered using a filter having a pore size of about 0.2 ⁇ m.
  • a solution of the cured film forming composition of the present invention is applied to a substrate (for example, a silicon / silicon dioxide-coated substrate, a silicon nitride substrate, a substrate coated with a metal such as aluminum, molybdenum, or chromium, a glass substrate, a quartz substrate, or ITO.
  • a substrate for example, a silicon / silicon dioxide-coated substrate, a silicon nitride substrate, a substrate coated with a metal such as aluminum, molybdenum, or chromium, a glass substrate, a quartz substrate, or ITO.
  • Substrates) and film substrates for example, resin films such as triacetyl cellulose (TAC) film, cycloolefin polymer (COP) film, cycloolefin copolymer (COC) film, polyethylene terephthalate (PET) film, acrylic film, polyethylene film)
  • TAC triacetyl cellulose
  • COC cycloolefin polymer
  • COC cycloolefin copolymer
  • PET polyethylene terephthalate
  • Acrylic film polyethylene film
  • Etc. by bar coating, spin coating, flow coating, roll coating, slit coating, spin coating following slit, ink jet coating, printing, etc. to form a coating film, and then using a hot plate or oven, etc. Heat drying By, it can form a cured film.
  • the cured film can be applied as an alignment material as it is.
  • the heating and drying conditions may be such that the crosslinking reaction with the crosslinking agent proceeds to such an extent that the components of the cured film (alignment material) do not elute into the polymerizable liquid crystal solution applied thereon.
  • a heating temperature and a heating time appropriately selected from the range of 200 ° C. and a time of 0.4 minutes to 60 minutes are adopted.
  • the heating temperature and the heating time are preferably 70 to 160 ° C. and 0.5 to 10 minutes.
  • the thickness of the cured film (alignment material) formed using the curable composition of the present invention is, for example, 0.05 ⁇ m to 5 ⁇ m, and is appropriately determined in consideration of the level difference of the substrate to be used and optical and electrical properties. You can choose.
  • a phase difference material such as a polymerizable liquid crystal solution having vertical alignment property is applied onto the alignment material. Can be oriented on the orientation material. Then, the retardation material in an oriented state can be cured by irradiating with ultraviolet rays of 300 to 400 nm to form a retardation material as a layer having optical anisotropy. And when the board
  • the alignment materials on both substrates are bonded to each other via a spacer, and then between the substrates.
  • a liquid crystal display element in which liquid crystal is injected to align the liquid crystal may be used.
  • the cured film forming composition of this invention can be used suitably for manufacture of various retardation materials (retardation film), a liquid crystal display element, etc.
  • ⁇ (B) component cross-linking agent>
  • CYM303 Hexamethoxymethylmelamine
  • ⁇ (C) component acid catalyst>
  • PTSA p-toluenesulfonic acid monohydrate
  • the number average molecular weight and weight average molecular weight of the acrylic copolymer obtained in accordance with the following synthesis examples were measured using a GPC apparatus (Shodex (registered trademark) columns KF803L and KF804L) manufactured by JASCO Corporation, and the elution solvent tetrahydrofuran at a flow rate of 1 mL. It was measured under the condition that the column was eluted at a rate of 40 minutes per minute (column temperature: 40 ° C.).
  • Mn number average molecular weight
  • Mw weight average molecular weight
  • Examples 1 to 7, Comparative Examples 1 and 2 The cured film forming compositions of Examples 1 to 7 and Comparative Examples 1 and 2 were prepared with the compositions shown in Table 1, and vertical alignment was evaluated for each.
  • the retardation material using the cured film obtained from the cured film forming composition of Examples 1 to 7 as an alignment material does not depend on the base material used, and all have good vertical alignment properties. In addition, the coating property of the liquid crystal was also good.
  • a retardation material using a cured film obtained from the cured film forming composition of Comparative Example 1 containing neither of the crosslinking agent (B) and the acid catalyst (C) as an aligning agent, and a vertical alignment group The phase difference material using the cured film obtained from the cured film forming composition of Comparative Example 2 using the component (A) that does not contain as the alignment material did not have vertical alignment.
  • the retardation material of Comparative Example 3 obtained without forming a cured film showed vertical alignment on glass but did not show vertical alignment on PET.
  • the cured film forming composition according to the present invention is very useful as a material for forming a liquid crystal alignment film of a liquid crystal display element and an alignment material for forming an optically anisotropic film provided inside or outside the liquid crystal display element.
  • it is suitable as a material for an optical compensation film of IPS-LCD.

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Liquid Crystal (AREA)
  • Polarising Elements (AREA)
  • Epoxy Resins (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)

Abstract

[Problème] L'invention concerne une composition formant un film durci à des fins de mise en œuvre d'un matériau d'alignement qui a des propriétés d'alignement vertical supérieures et qui est en mesure d'aligner à la verticale des cristaux liquides polymérisables tout en faisant preuve d'une forte sensibilité même sur un film de résine et à des fins de mise en œuvre d'un matériau de déphasage qui utilise un tel matériau d'alignement. [Solution] L'invention concerne une composition formant un film durci, caractérisée en ce qu'elle comporte : (A) un polymère obtenu en faisant réagir le groupe carboxyle d'un composé ayant un groupe carboxyle et un groupe à alignement vertical par rapport au groupe époxydique d'un polymère ayant au moins un groupe époxydique sur une chaîne latérale ou extrémité de celui-ci; et au moins un composé sélectionné dans le groupe constitué par (B) un agent de réticulation et (C) un catalyseur acide. L'invention concerne aussi un matériau d'alignement, caractérisé en ce qu'il est obtenu au moyen de ladite composition. L'invention concerne aussi un matériau de déphasage, caractérisé en ce qu'il est obtenu au moyen de ladite composition.
PCT/JP2014/072320 2013-08-29 2014-08-26 Composition formant un film durci, matériau d'alignement et matériau de déphasage Ceased WO2015030004A1 (fr)

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JP2015534237A JP6460340B2 (ja) 2013-08-29 2014-08-26 硬化膜形成組成物、配向材および位相差材
CN201480046361.8A CN105474083B (zh) 2013-08-29 2014-08-26 固化膜形成用组合物、取向材及相位差材
KR1020167005250A KR102193060B1 (ko) 2013-08-29 2014-08-26 경화막 형성 조성물, 배향재 및 위상차재

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KR102193060B1 (ko) 2020-12-18
TWI653287B (zh) 2019-03-11
JPWO2015030004A1 (ja) 2017-03-02
TWI653285B (zh) 2019-03-11
KR20160052545A (ko) 2016-05-12
CN105474083B (zh) 2019-10-08
TW201839048A (zh) 2018-11-01
TW201522484A (zh) 2015-06-16
CN105474083A (zh) 2016-04-06

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