[go: up one dir, main page]

WO2017065078A1 - Composition de cristaux liquides nématiques, et élément d'affichage à cristaux liquides mettant en œuvre celle-ci - Google Patents

Composition de cristaux liquides nématiques, et élément d'affichage à cristaux liquides mettant en œuvre celle-ci Download PDF

Info

Publication number
WO2017065078A1
WO2017065078A1 PCT/JP2016/079760 JP2016079760W WO2017065078A1 WO 2017065078 A1 WO2017065078 A1 WO 2017065078A1 JP 2016079760 W JP2016079760 W JP 2016079760W WO 2017065078 A1 WO2017065078 A1 WO 2017065078A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
formula
carbon atoms
independently
liquid crystal
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/JP2016/079760
Other languages
English (en)
Japanese (ja)
Inventor
平田　真一
直美 幡野
淳子 山本
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.)
DIC Corp
Original Assignee
DIC Corp
Dainippon Ink and Chemicals Co Ltd
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 DIC Corp, Dainippon Ink and Chemicals Co Ltd filed Critical DIC Corp
Priority to CN201680055198.0A priority Critical patent/CN108026449A/zh
Priority to JP2017545174A priority patent/JPWO2017065078A1/ja
Publication of WO2017065078A1 publication Critical patent/WO2017065078A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
    • C07C25/18—Polycyclic aromatic halogenated hydrocarbons
    • C07C25/22—Polycyclic aromatic halogenated hydrocarbons with condensed 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
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/38—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
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers

Definitions

  • the present invention relates to a nematic liquid crystal composition containing a polymerizable compound and a liquid crystal display device using the same.
  • a PSA (Polymer Sustained Alignment) type liquid crystal display element has a polymer structure formed in a cell to control the pretilt angle of liquid crystal molecules, and is practical as a liquid crystal display element having features such as high-speed response and high contrast. It has become.
  • a PSA-type liquid crystal display device is a liquid crystal display device manufactured using a polymerizable compound-containing liquid crystal composition comprising a liquid crystal compound and a polymerizable compound, and polymerizes the polymerizable compound in a state where liquid crystal molecules are aligned by voltage application. And by fixing the alignment of the liquid crystal molecules.
  • the polymerization reaction rate of the polymerizable compound is very important for productivity. It is also very important to adjust the pretilt angle that affects the response speed and contrast of the PSA type liquid crystal display element and the residual amount of the polymerizable compound that affects the reliability such as display unevenness and image sticking.
  • the polymerization reaction rate of the polymerizable compound depends on the wavelength and irradiation intensity of the UV irradiation lamp, development of a polymerizable compound-containing liquid crystal composition containing the polymerizable compound adapted to the specifications of the UV irradiation lamp is required. However, sufficient response was difficult.
  • a composition containing a liquid crystal compound having a terphenyl ring (Patent Document 1) or a composition containing a liquid crystal compound having a naphthalene ring and a phenyl ring ( Patent Document 2) introduces a technique for reducing the polymerization reaction rate.
  • VHR voltage holding ratio
  • liquid crystal composition containing a polymerizable compound that suppresses adverse effects such as high-speed response, high contrast, display unevenness, and image sticking of the liquid crystal display element at the same time as adjusting the polymerization reaction speed adapted to the specifications of the UV irradiation lamp
  • the problem to be solved by the present invention is that the viscosity ( ⁇ ) is sufficiently small, the rotational viscosity ( ⁇ 1) is sufficiently small, the polymerizable compound reacts sufficiently fast, and there is no residue of the polymerizable compound after UV irradiation.
  • a liquid crystal display element such as a PSA type in which VHR is good and display unevenness or image sticking does not occur or is extremely suppressed.
  • R 11 and R 12 are each independently an alkyl group having 1 to 10 carbon atoms, an alkoxyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or 2 carbon atoms.
  • To 10 alkenyloxy groups, and one or more hydrogen atoms present in these groups may be substituted by fluorine atoms
  • X 11 to X 20 are each independently a hydrogen atom.
  • L 11 and L 12 are each independently —OCH 2 —, —CH 2 O—, —CF 2 O—, —OCF 2 —.
  • m 11 and m 12 each independently represent 0 or 1
  • m 11 + m 12 represents 1 or 2.
  • the viscosity ( ⁇ ) of the composition of the present invention is sufficiently low, the liquid crystal display device using the composition has a sufficiently high response speed and can display 3D, and there is no residual polymerizable compound. Since it is sufficiently suppressed, VHR is good and display unevenness or image sticking does not occur or is extremely suppressed. Further, since the polymerization reaction rate of the polymerizable compound is sufficiently high, the energy cost for production can be reduced, the production efficiency can be improved, and uniform and stable alignment control can be obtained, which is very useful.
  • composition of the present invention has the general formula (I)
  • the compound represented by the general formula (I) has a structure having a naphthalene ring, a phenyl ring, and one or more cyclohexane rings.
  • R 11 and R 12 are each independently an alkyl group having 1 to 10 carbon atoms, an alkoxyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or carbon. Represents an alkenyloxy group having 2 to 10 atoms, and one or more hydrogen atoms present in these groups may be substituted by a fluorine atom, but an alkyl group having 1 to 5 carbon atoms, Preferred are an alkoxyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 5 carbon atoms, an alkyl group having 1 to 5 carbon atoms, and an alkyl group having 1 to 5 carbon atoms.
  • An alkoxyl group or an alkenyl group having 2 to 5 carbon atoms is preferable, and an alkyl group having 1 to 5 carbon atoms or an alkoxyl group having 1 to 5 carbon atoms is more
  • X 11 to X 20 each independently represents a hydrogen atom, a methyl group, —CF 3 group, a fluorine atom or a chlorine atom, preferably a hydrogen atom, a methyl group or a fluorine atom, and preferably a hydrogen atom or a fluorine atom It is more preferable that two or three of X 11 to X 20 are fluorine atoms, and the other is a hydrogen atom, and two of X 11 to X 20 are fluorine atoms. The other is particularly preferably a hydrogen atom.
  • L 11 and L 12 are each independently —OCH 2 —, —CH 2 O—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 CF 2 — or a single bond represents a, -OCH 2 -, - CH 2 O -, - it is or a single bond - CH 2 CH 2 - that or a single bond preferably, -CH 2 CH 2 is a structure containing no oxygen atom Is more preferable, and a single bond is more preferable.
  • n 11 and m 12 each independently represent 0 or 1, and m 11 + m 12 represents 1 or 2, but m 11 + m 12 is preferably 1.
  • the compound represented by general formula (I) contains 1 type, or 2 or more types, it is preferable to contain 1 type to 5 types, it is more preferable to contain 1 type to 3 types, and 1 type is contained. Is particularly preferred. Further, the content thereof is 0.1% to 50% by mass, preferably 0.1% to 10% by mass, and 0.3% to 8% by mass with respect to the composition. The range is more preferably 0.5% by mass to 5% by mass, 0.5% to 3% by mass, and 0.5% to 2% by mass. May be.
  • the compound represented by general formula (I) is preferably a compound represented by general formula (N-002) to general formula (N-079).
  • the compounds represented by the general formula (N-002) to the general formula (N-079) the compounds represented by the general formula (N-030) to the general formula (N-042), 058) to general formula (N-062), general formula (N-071) to general formula (N-074), general formula (N-077) to general formula (N— 079) is preferred, and compounds represented by general formula (N-030) to general formula (N-035) are more preferred.
  • composition of the present invention contains one or more polymerizable compounds.
  • the polymerizable compound preferably has a mesogenic skeleton, specifically, the general formula (M)
  • R 201 is, P 201 -Sp 201 - represents, R 202 is, P 202 -Sp 202 - represents a.
  • P 201 and P 202 each independently represent formula (R-1) to formula (R-15)
  • P 201 and P 202 may be the same or different.
  • Sp 201 and Sp 202 each independently represent a single bond or an alkylene group having 1 to 15 carbon atoms, and one or two or more —CH 2 — in the alkylene group is not directly adjacent to an oxygen atom. May be substituted with —O—, —OCO— or —COO—, but each independently represents a single bond or a carbon number in which one methylene may be substituted with —O—, —OCO— or —COO—.
  • at least one is preferably a single bond, one is a single bond and the other is an alkylene group having 1 to 4 carbon atoms, or — O— (CH 2 ) s — is preferable.
  • an alkylene group having 1 to 4 carbon atoms is preferable, and s is preferably 1 to 4. It is also preferable that both Sp 201 and Sp 202 are single bonds.
  • M 201 , M 202 and M 203 are each independently a phenyl group, 1,4-phenylene group, benzene-1,2,4-triyl group, benzene-1,2,4,6-tetrayl group, 1, 4-cyclohexylene group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, naphthyl group, naphthalene-2,6-diyl group, indan-2,5-diyl group, 1,2,3 , 4-tetrahydronaphthalene-2,6-diyl group or 1,3-dioxane-2,5-diyl group, the group being unsubstituted or an alkyl group having 1 to 12 carbon atoms, 1 carbon atom May be substituted with an alkoxyl group of ⁇ 12, halogen, cyano group or nitro group, but each independently is unsubstituted or substituted with an alkyl group
  • n 201 , n 202 and n 203 each independently represents an integer of 0 to 3, and the total number of n 201 and n 203 is 2 or more, but n 202 is preferably 0, 1 or 2 0 or 1 is more preferable.
  • n 201 and n 203 are each independently preferably 0, 1 or 2, more preferably 1 or 2, and the total number of n 201 and n 203 is preferably 2 or 3.
  • a plurality of existing P 201 , P 202 , Sp 201 , Sp 202 , Z 201, and M 202 may be the same or different.
  • the composition of the present invention contains at least one polymerizable compound represented by formula (M), preferably 1 to 5 types, more preferably 1 to 3 types.
  • the orientation control power with respect to a liquid-crystal composition becomes weak.
  • the content of the polymerizable compound represented by the general formula (M) is too large, the energy required for the polymerization of the polymerizable compound increases, and the amount of the polymerizable compound that remains without being polymerized increases.
  • the content is preferably 0.01 to 2.00% by mass, and more preferably 0.05 to 1.00% by mass. 0.10 to 0.50% by mass is particularly preferable.
  • the ring structure between Sp 201 and Sp 202 is the formula (XXa-1) to the formula (XXa-5).
  • the formula (XXa-1) to the formula (XXa-3) are more preferable, and the formula (XXa-1) or the formula (XXa-2) is particularly preferable.
  • both ends of the equation shall be connected to Sp 201 or Sp 202 .
  • the polymerizable compound represented by the general formula (M) containing these skeletons is preferable for a PSA mode liquid crystal display element because of its orientation regulating force after polymerization.
  • Sp xx represents an alkylene group having 1 to 8 carbon atoms or —O— (CH 2 ) s — (wherein s represents an integer of 2 to 7, and an oxygen atom is bonded to the ring. ).
  • the hydrogen atom in the phenyl group in the formula may be further substituted by —F, —Cl, —CF 3 , —CH 3 , or any one of formulas (R-1) to (R-15). .
  • n 202 is 1, for example, a polymerizable compound such as the formula (M31) to the formula (M52) is preferable.
  • the hydrogen atom in the phenyl group and naphthalene group in the formula is further substituted with —F, —Cl, —CF 3 , —CH 3 , or any one of formulas (R-1) to (R-15). May be.
  • the polymerizable compound represented by the general formula (M) containing these skeletons is preferable for a PSA mode liquid crystal display element because of its orientation regulating force after polymerization.
  • n 201 is 1, n 202 is 1, and n 203 is 2, for example, a polymerizable compound such as formula (M301) to formula (M320) is preferable.
  • the hydrogen atom in the phenyl group and naphthalene group in the formula may be further substituted with —F, —Cl, —CF 3 , —CH 3 .
  • the polymerizable compound represented by the general formula (M) containing these skeletons is preferable for a PSA mode liquid crystal display element because of its orientation regulating force after polymerization.
  • composition of the present invention further has the general formula (N-1)
  • R N11 and R N12 are each independently an alkyl group having 1 to 10 carbon atoms, an alkoxyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or 2 carbon atoms
  • R N11 and R N12 in present in one -CH 2 - or nonadjacent two or more -CH 2 - are each independently -O- and / or -S
  • one or two or more hydrogen atoms present in R N11 and R N12 may each independently be substituted with a fluorine atom or a chlorine atom
  • a N11 represents 1 , 4-cyclohexylene group (this is present in the group one -CH 2 - or nonadjacent two or more -CH 2 -.
  • -O- 1,4 Phenylene group
  • -N 1,4 Phenylene group
  • n N11 1 or 2
  • Z N11 is - OCH 2 —, —CH 2 O—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 CF 2 — or a single bond
  • a plurality of existing A N11 are the same. Or may be different.
  • the compound represented by the general formula (N-1) is contained in one or more kinds, preferably 1 to 10 kinds, more preferably 1 to 6 kinds,
  • the content is preferably 10% by mass to 90% by mass, more preferably 10% by mass to 70% by mass, and particularly preferably 20% by mass to 50% by mass with respect to the composition.
  • R N11 and R N12 each independently represent an alkyl group having 1 to 5 carbon atoms, an alkoxyl group having 1 to 5 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms. Or an alkenyloxy group having 2 to 5 carbon atoms, R N11 is an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and R N12 is 1 carbon atom. And more preferably an alkyl group having 1 to 5 carbon atoms or an alkoxyl group having 1 to 5 carbon atoms.
  • a N11 is 1,4-cyclohexylene group or 1,4-phenylene group is preferred.
  • Z N11 is, -CH 2 O -, - CH 2 CH 2 - or preferably a single bond, more preferably -CH 2 O-or a single bond.
  • the compound represented by the general formula (N-1) is represented by the general formula (N-1-1) to the general formula (N-1-4), the general formula (N-1-10) or the general formula.
  • R N111 and R N112 each independently represent the same meaning as R N11 and R N12 in formula (N-1)).
  • R N121 and R N122 each independently represent the same meaning as R N11 and R N12 in formula (N-1)).
  • R N131 and R N132 each independently represent the same meaning as R N11 and R N12 in formula (N-1)).
  • R N141 and R N142 each independently represents the same meaning as R N11 and R N12 in the general formula (N-1).
  • R N1101 and R N1102 each independently represent the same meaning as R N11 and R N12 in formula (N-1).
  • R N1111 and R N1112 each independently represent the same meaning as R N11 and R N12 in formula (N-1)) are preferable.
  • the compound represented by the general formula (N-1-1) can be used alone, or two or more compounds can be used in combination. it can. There are no particular restrictions on the types of compounds that can be combined, but they are used in appropriate combinations according to the required properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence.
  • the kind of the compound used is, for example, one kind as one embodiment of the present invention, two kinds, three kinds, four kinds, and five kinds or more.
  • the lower limit of the preferable content of the compound represented by the general formula (N-1-1) with respect to the total amount of the composition of the present invention is 5%, 10%, 13%, 15% %, 17%, 20%, 23%, 25%, 27%, 30%, 33%, and 35%.
  • the upper limit of the preferable content is 50%, 40%, 38%, 35%, 33%, 30%, and 28% with respect to the total amount of the composition of the present invention. %, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6% %, 5%, 3%.
  • the compound represented by the general formula (N-1-1) can be used alone, or two or more compounds can be used in combination.
  • the kind of the compound used is, for example, one kind as one embodiment of the present invention, two kinds, three kinds, four kinds, and five kinds or more.
  • the lower limit of the preferable content of the compound represented by the general formula (N-1-1) with respect to the total amount of the composition of the present invention is 5%, 10%, 13%, 15% %, 17%, 20%, 23%, 25%, 27%, 30%, 33%, and 35%.
  • the upper limit of the preferable content is 50%, 40%, 38%, 35%, 33%, 30%, and 28% with respect to the total amount of the composition of the present invention. %, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6% %, 5%, 3%.
  • the compound represented by the general formula (N-1-1) is specifically selected from the group of compounds represented by the formula (N-1-4.1) to the formula (N-1-4.14).
  • the compounds represented by formulas (N-4-1.1) to (N-1-1.4) are preferred, and the compounds represented by formulas (N-1-1.1) and A compound represented by the formula (N-1-1.3) is preferred.
  • the compounds represented by formulas (N-1-1.1) to (N-1-1.14) can be used alone or in combination.
  • the lower limit of the preferred content of these compounds alone or with respect to the total amount is 5%, 10%, 13%, 15%, 17%, 20%, 23% 25% 27% 30% 33% 35%
  • the upper limit of the preferable content is 50%, 40%, 38%, 35%, 33%, 30%, and 28% with respect to the total amount of the composition of the present invention. %, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6% %, 5%, 3%.
  • the compound represented by the general formula (N-1-2) can be used alone, or two or more compounds can be used in combination. it can. There are no particular restrictions on the types of compounds that can be combined, but they are used in appropriate combinations according to the required properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence.
  • the kind of the compound used is, for example, one kind as one embodiment of the present invention, two kinds, three kinds, four kinds, and five kinds or more.
  • the lower limit of the preferable content of the compound represented by the general formula (N-1-2) with respect to the total amount of the composition of the present invention is 5%, 7%, 10%, %, 15%, 17%, 20%, 23%, 25%, 27%, 30%, 33%, 35%, 37 %, 40%, and 42%.
  • the upper limit of the preferable content is 50%, 48%, 45%, 43%, 40%, 38%, and 35% with respect to the total amount of the composition of the present invention. %, 33%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10% %, 8%, 7%, 6%, 5%.
  • the compound represented by the general formula (N-1-2) is specifically a compound group represented by the formula (N-1-2.1) to the formula (N-1-2.13).
  • the compound is selected from the formulas (N-1-2.3) to (N-1-2.7), (N-1-2.10), and (N-1-2). .11) and the compound represented by formula (N-1-2.13).
  • the compound represented by formula (N-1-2.3) to formula (N-1 is preferably a compound represented by -2.7), formula (N-1-2.10 in the case of emphasizing improvements in T NI), the formula (N-1-2.11) and formula (N-1 -2.13) is preferred.
  • the compounds represented by the formula (N-1-2.1) to the formula (N-1-2.13) can be used alone or in combination.
  • the lower limit of the preferable content of these compounds alone or with respect to the total amount of is 5%, 10%, 13%, 15%, 17%, 20%, 23 %, 25%, 27%, 30%, 33%, and 35%.
  • the upper limit of the preferable content is 50%, 40%, 38%, 35%, 33%, 30%, and 28% with respect to the total amount of the composition of the present invention. %, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6% %, 5%, 3%.
  • the compound represented by the general formula (N-1-3) can be used alone, or two or more compounds can be used in combination. it can. There are no particular restrictions on the types of compounds that can be combined, but they are used in appropriate combinations according to the required properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence.
  • the kind of the compound used is, for example, one kind as one embodiment of the present invention, two kinds, three kinds, four kinds, and five kinds or more.
  • the lower limit of the preferable content of the compound represented by the general formula (N-1-3) with respect to the total amount of the composition of the present invention is 5%, 10%, 13%, 15% %, 17% and 20%.
  • the upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, 20%, and 18% with respect to the total amount of the composition of the present invention. %, 15%, and 13%.
  • the compound represented by the general formula (N-1-3) is specifically a group of compounds represented by the formula (N-1-3.1) to the formula (N-1-3.11).
  • a compound selected from the group consisting of formulas (N-1-3.1) to (N-1-3.7) is preferable, and a compound represented by formula (N-1-3.1) is preferable.
  • Formula (N-1-3.2), formula (N-1-3.3), formula (N-1-3.4) and compound represented by formula (N-1-3.6) Is preferred.
  • the compounds represented by formula (N-1-3.1) to formula (N-1-3.4) and formula (N-1-3.6) may be used alone or in combination. Is possible, but the combination of formula (N-1-3.1) and formula (N-1-3.2), formula (N-1-3.3), formula (N-1-3.4) ) And a combination of two or three selected from formula (N-1-3.6) are preferred.
  • the lower limit of the preferred content of these compounds alone or with respect to the total amount of the composition of the present invention is 5%, 10%, 13%, 15%, 17%, 20% %.
  • the upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, 20%, and 18% with respect to the total amount of the composition of the present invention. %, 15%, and 13%.
  • the compound represented by the general formula (N-1-4) can be used alone, or two or more compounds can be used in combination. it can. There are no particular restrictions on the types of compounds that can be combined, but they are used in appropriate combinations according to the required properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence.
  • the kind of the compound used is, for example, one kind as one embodiment of the present invention, two kinds, three kinds, four kinds, and five kinds or more.
  • the lower limit of the preferable content of the compound represented by the general formula (N-1-4) with respect to the total amount of the composition of the present invention is 3%, 5%, 7%, 10% %, 13%, 15%, 17%, and 20%.
  • the upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, 20%, and 18% with respect to the total amount of the composition of the present invention. %, 15%, 13%, 11%, 10%, and 8%.
  • the compound represented by the general formula (N-1-4) is specifically selected from the group of compounds represented by the formula (N-1-4.1) to the formula (N-1-4.14)
  • the compounds represented by formulas (N-1-4.1) to (N-1-4.4) are preferred, and the compounds represented by formulas (N-1-4.1) and A compound represented by the formula (N-1-4.2) is preferable.
  • the compounds represented by formulas (N-1-4.1) to (N-1-4.4) can be used singly or in combination, but the compounds of the present invention
  • the lower limit of the preferable content of these compounds alone or with respect to the total amount is 3%, 5%, 7%, 10%, 13%, 15%, 17% And 20%.
  • the upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, 20%, and 18% with respect to the total amount of the composition of the present invention. %, 15%, 13%, 11%, 10%, and 8%.
  • the compound represented by the general formula (N-1) can be used alone, or two or more compounds can be used in combination. it can. There are no particular restrictions on the types of compounds that can be combined, but they are used in appropriate combinations according to the required properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence.
  • the kind of the compound used is, for example, one kind as one embodiment of the present invention, two kinds, three kinds, four kinds, and five kinds or more.
  • the lower limit of the preferable content of the compound represented by the general formula (N-1-10) with respect to the total amount of the composition of the present invention is 5%, 10%, 13%, 15% %, 17% and 20%.
  • the upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, 20%, and 18% with respect to the total amount of the composition of the present invention. %, 15%, and 13%.
  • the compound represented by the general formula (N-1-10) is specifically a group of compounds represented by the formula (N-1-10.1) to the formula (N-1-10.15).
  • a compound selected from the group consisting of formulas (N-1-10.1) to (N-1-10.5) is preferable.
  • a compound represented by the formula (N-1-10.2) are preferable.
  • the compounds represented by the formula (N-1-10.1) and the formula (N-1-10.2) can be used alone or in combination.
  • the lower limit of the preferable content of these compounds alone or with respect to the total amount is 5%, 10%, 13%, 15%, 17%, and 20%.
  • the upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, 20%, and 18% with respect to the total amount of the composition of the present invention. %, 15%, and 13%.
  • the compound represented by the general formula (N-1-11) can be used alone, but two or more compounds are used in combination. You can also. There are no particular restrictions on the types of compounds that can be combined, but they are used in appropriate combinations according to the required properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence.
  • the kind of the compound used is, for example, one kind as one embodiment of the present invention, two kinds, three kinds, four kinds, and five kinds or more.
  • the lower limit of the preferred content of the compound represented by formula (N-1-11) with respect to the total amount of the composition of the present invention is 5%, 10%, 13%, 15% %, 17% and 20%.
  • the upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, 20%, and 18% with respect to the total amount of the composition of the present invention. %, 15%, and 13%.
  • the compound represented by the general formula (N-1-11) specifically includes a compound group represented by the formula (N-1-11.1) to the formula (N-1-11.15).
  • the compound is preferably a compound selected from formulas (N-1-11.1) to (N-1-11.15), and preferably represented by formula (N-1-111.2).
  • a compound represented by formula (N-1-11.4) is preferable.
  • the compounds represented by the formula (N-1-11.2 and the formula (N-1-11.4) can be used alone or in combination.
  • the lower limit of the preferable content of these compounds alone or with respect to the total amount is 5%, 10%, 13%, 15%, 17%, and 20%.
  • the upper limit of the amount is 35%, 30%, 28%, 25%, 23%, 20%, 18% with respect to the total amount of the composition of the present invention. Yes, 15%, 13%.
  • composition of the present invention has a general formula (L-1) to a general formula (L-6) as a compound having a dielectric anisotropy ( ⁇ ) of almost 0.
  • R L11 to R L62 each independently represents an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms
  • X L61 and X L62 each independently represent a hydrogen atom or fluorine It is preferable to contain a compound selected from the group consisting of compounds represented by the formula:
  • composition of the present invention preferably contains the compounds of general formula (I), general formula (M) and general formula (N-1) at the same time, and includes general formula (I), general formula (M) and general formula (N-1). More preferably, the compound of (N-1) and the general formula (L-1) are simultaneously contained.
  • the composition of the present invention comprises a compound represented by general formula (I), a compound represented by general formula (M), a compound represented by general formula (N-1), and general formula (L-1) to
  • the total amount of compounds selected from the compound group represented by formula (L-6) is preferably 85% by mass to 100% by mass, more preferably 90% by mass to 100% by mass, and 95% by mass. To 100% by mass, and more preferably 98% to 100% by mass.
  • the compound having an alkenyl group is preferably 12% by mass or less, More preferably, it is not contained at all, and the cyclohexane ring or benzene ring in the liquid crystal compound may be substituted with a fluorine atom, but is not preferably substituted with a chlorine atom.
  • the composition of the present invention has a dielectric anisotropy ( ⁇ ) at 25 ° C. of ⁇ 2.0 to ⁇ 8.0, preferably ⁇ 2.0 to ⁇ 6.0, and ⁇ 2.0 to ⁇ 5.0 is more preferable, and ⁇ 2.5 to ⁇ 4.0 is even more preferable.
  • the composition of the present invention has a refractive index anisotropy ( ⁇ n) at 20 ° C. of 0.08 to 0.14, more preferably 0.09 to 0.13, and particularly preferably 0.09 to 0.12. preferable. More specifically, when it corresponds to a thin cell gap, it is preferably 0.10 to 0.125, and when it corresponds to a thick cell gap, it is preferably 0.08 to 0.10.
  • the composition of the present invention has a viscosity ( ⁇ ) at 20 ° C. of 10 to 30 mPa ⁇ s, more preferably 10 to 25 mPa ⁇ s, and particularly preferably 10 to 22 mPa ⁇ s.
  • the composition of the present invention has a rotational viscosity ( ⁇ 1 ) at 20 ° C. of 60 to 130 mPa ⁇ s, more preferably 60 to 110 mPa ⁇ s, and particularly preferably 60 to 100 mPa ⁇ s.
  • composition of the present invention has a nematic phase-isotropic liquid phase transition temperature (T ni ) of 60 ° C to 120 ° C, more preferably 68 ° C to 100 ° C, and particularly preferably 68 ° C to 85 ° C.
  • T ni nematic phase-isotropic liquid phase transition temperature
  • the polymerization proceeds even in the absence of a polymerization initiator, but may contain a polymerization initiator in order to accelerate the polymerization.
  • the polymerization initiator include benzoin ethers, benzophenones, acetophenones, benzyl ketals, acylphosphine oxides, and the like.
  • composition of the present invention may further contain a compound represented by the general formula (Q).
  • R Q represents a linear or branched alkyl group having 1 to 22 carbon atoms, and one or two or more non-adjacent CH 2 groups in the group are —O—, —CH ⁇ CH—, —CO—, —OCO—, —COO—, —C ⁇ C—, —CF 2 O—, —OCF 2 — may be substituted.
  • MQ represents a trans-1,4-cyclohexylene group, a 1,4-phenylene group or a single bond.
  • the compound represented by the general formula (Q) is preferably a compound represented by the following general formula (Qa) to general formula (Qd).
  • R Q1 is preferably a linear alkyl group or a branched alkyl group having 1 to 10 carbon atoms.
  • R Q2 is preferably a linear alkyl group having 1 to 20 carbon atoms or a branched alkyl group.
  • R Q3 is preferably a linear alkyl group having 1 to 8 carbon atoms, a branched alkyl group, a linear alkoxy group, or a branched alkoxy group.
  • L Q is preferably a linear alkylene group or branched alkylene group having 1 to 8 carbon atoms.
  • the composition of the present invention preferably contains one or more compounds represented by the general formula (Q), preferably contains 1 to 5 types, and preferably contains 1 to 3 types. More preferably, it is more preferable to contain 1 type. Further, the content is preferably 0.001% by mass to 1% by mass, more preferably 0.001% by mass to 0.1% by mass, and further preferably 0.001% by mass to 0.05% by mass. .
  • a stabilizer may be added to improve storage stability.
  • examples of the stabilizer that can be used include hydroquinones, hydroquinone monoalkyl ethers, tert-butylcatechols, pyrogallols, thiophenols, nitro compounds, ⁇ -naphthylamines, ⁇ -naphthols, nitroso compounds, and the like. It is done.
  • composition of the present invention may contain a normal nematic liquid crystal, smectic liquid crystal, cholesteric liquid crystal, antioxidant, ultraviolet absorber, polymerizable monomer and the like in addition to the above-mentioned compounds.
  • composition of the present invention is useful for a liquid crystal display device, particularly useful for a liquid crystal display device for driving an active matrix, and used for a liquid crystal display device for a PSA mode, a PSVA mode, a VA-IPS mode or a polymer stabilization mode. be able to.
  • the composition of the present invention is a liquid crystal display element in which the polymerizable compound contained therein is polymerized by ultraviolet irradiation to impart liquid crystal alignment ability, and the amount of transmitted light is controlled using the birefringence of the liquid crystal composition.
  • a liquid crystal display element it is useful for an AM-LCD (active matrix liquid crystal display element) and an IPS-LCD (in-plane switching liquid crystal display element), but is particularly useful for an AM-LCD and is a transmissive or reflective liquid crystal display. It can be used for an element.
  • the two substrates of the liquid crystal cell used in the liquid crystal display element can be made of a transparent material having flexibility such as glass or plastic, and one of them can be an opaque material such as silicon.
  • a transparent substrate having a transparent electrode layer can be obtained, for example, by sputtering indium tin oxide (ITO) on a transparent substrate such as a glass plate.
  • the color filter can be prepared by, for example, a pigment dispersion method, a printing method, an electrodeposition method, or a dyeing method.
  • a method for producing a color filter by a pigment dispersion method will be described as an example.
  • a curable coloring composition for a color filter is applied on the transparent substrate, subjected to patterning treatment, and cured by heating or light irradiation. By performing this process for each of the three colors red, green, and blue, a pixel portion for a color filter can be created.
  • a pixel electrode provided with an active element such as a TFT, a thin film diode, or a metal insulator metal specific resistance element may be provided on the substrate.
  • the substrate is opposed so that the transparent electrode layer is on the inside.
  • the thickness of the obtained light control layer is 1 to 100 ⁇ m. More preferably, the thickness is 1.5 to 10 ⁇ m.
  • the polarizing plate it is preferable to adjust the product of the refractive index anisotropy ⁇ n of the liquid crystal and the cell thickness d so that the contrast is maximized.
  • the polarizing axis of each polarizing plate can be adjusted so that the viewing angle and contrast are good.
  • a retardation film for widening the viewing angle can also be used.
  • the spacer examples include glass particles, plastic particles, alumina particles, and a photoresist material.
  • a sealant such as an epoxy thermosetting composition is screen-printed on the substrates with a liquid crystal inlet provided, the substrates are bonded together, and heated to thermally cure the sealant.
  • a normal vacuum injection method or an ODF method can be used as a method of sandwiching the composition of the present invention between two substrates.
  • an appropriate polymerization rate is desirable in order to obtain good alignment performance of liquid crystals. Therefore, active energy rays such as ultraviolet rays or electron beams are irradiated singly or in combination or sequentially.
  • the method of polymerizing by is preferred.
  • a polarized light source or a non-polarized light source may be used.
  • at least the substrate on the irradiated surface side must be given appropriate transparency to the active energy rays.
  • the orientation state of the unpolymerized part is changed by changing conditions such as an electric field, a magnetic field, or temperature, and further irradiation with active energy rays is performed. Then, it is possible to use a means for polymerization.
  • a means for polymerization In particular, when ultraviolet exposure is performed, it is preferable to perform ultraviolet exposure while applying an alternating electric field to the composition of the present invention.
  • the alternating electric field to be applied is preferably an alternating current having a frequency of 10 Hz to 10 kHz, more preferably a frequency of 60 Hz to 10 kHz, and the voltage is selected depending on a desired pretilt angle of the liquid crystal display element. That is, the pretilt angle of the liquid crystal display element can be controlled by the applied voltage. In the MVA mode liquid crystal display element, the pretilt angle is preferably controlled from 80 degrees to 89.9 degrees from the viewpoint of alignment stability and contrast.
  • the temperature during irradiation is preferably within a temperature range in which the liquid crystal state of the composition of the present invention is maintained. Polymerization is preferably performed at a temperature close to room temperature, that is, typically 15 to 35 ° C.
  • a lamp for generating ultraviolet rays a metal halide lamp, a high-pressure mercury lamp, an ultra-high pressure mercury lamp, or the like can be used.
  • a wavelength of the ultraviolet-rays to irradiate it is preferable to irradiate the ultraviolet-ray of the wavelength range which is not the absorption wavelength range of a liquid crystal composition, and it is preferable to cut and use an ultraviolet-ray as needed.
  • the intensity of the irradiated ultraviolet light is preferably 0.1 mW / cm 2 to 100 W / cm 2, more preferably 2 mW / cm 2 to 50 W / cm 2 .
  • the amount of energy of ultraviolet rays to be irradiated can be adjusted as appropriate, but is preferably 10 mJ / cm 2 to 500 J / cm 2, and more preferably 100 mJ / cm 2 to 200 J / cm 2 .
  • the intensity may be changed.
  • the time for irradiation with ultraviolet rays is appropriately selected depending on the intensity of ultraviolet rays to be irradiated, but is preferably 10 seconds to 3600 seconds, and more preferably 10 seconds to 600 seconds.
  • the measured characteristics are as follows.
  • T ni Nematic phase-isotropic liquid phase transition temperature (° C.)
  • ⁇ n Refractive index anisotropy at 20 ° C.
  • ⁇ Dielectric anisotropy at 20 ° C.
  • ⁇ 1 Rotational viscosity at 20 ° C. (mPa ⁇ s)
  • K 33 Elastic constant of bending at 20 ° C.
  • Pre-tilt angle Pre-tilt angle after UV irradiation by 20 J [°] / AUTRONIC-MELCHERS, TBA105 VHR / Initial: Voltage holding ratio before UV irradiation (1 V, 60 Hz, 60 ° C.) / Toyo Technica VHR-1 After VHR / UV20J: Voltage holding ratio after UV20J irradiation (1 V, 60 Hz, 60 ° C.) / Toyo Technica VHR-1 (Comparative Example 1, Comparative Example 2, Comparative Example 3 and Example 1) Polymeric compound-containing liquid crystal compositions of MLC-A1 (Comparative Example 1), MLC-A2 (Comparative Example 2), MLC-A3 (Comparative Example 3) and MLC-A4 (Example 1) were prepared, and their physical property values were prepared. Was measured. Table 1 shows the composition of the polymerizable compound-containing liquid crystal composition and the results of its physical properties.
  • MLC-A1 (Comparative Example 1)
  • MLC-A2 (Comparative Example 2)
  • MLC-A3 (Comparative Example 3)
  • MLC-A4 (Example 1) were each homeotropically aligned with a cell gap of 3.0 ⁇ m. It injected by the vacuum injection method to the cell with ITO which apply
  • PSVA liquid crystal display element in which the polymerizable compound in the polymerizable compound-containing liquid crystal composition was polymerized was obtained. It was confirmed that these PSVA liquid crystal display elements all showed an appropriate pretilt angle of about 88 ° and a response speed correlated with a physical property value.
  • VHR before and after UV irradiation and the amount of polymerizable compound remaining after UV irradiation were measured. The results are shown in Table 2.
  • Example 1 MLC-A4 has a significantly higher VHR after UV irradiation than MLC-A1 (Comparative Example 1), MLC-A2 (Comparative Example 2) and MLC-A3 (Comparative Example 3). In addition, it has been found that both of the characteristics that the remaining amount of the polymerizable compound is reduced are combined. Further, when a burn-in test was performed on these PSVA liquid crystal display elements, MLC-A1, MLC-A2 and MLC-A3 showed a burn-in which is considered to be caused by a low VHR or residual polymerizable compound after UV irradiation. . On the other hand, MLC-A4 did not generate any burn-in.
  • LC-A4 which is a polymerizable compound-containing liquid crystal composition of the present invention, has excellent UV resistance, a small residual amount of the polymerizable compound, and does not cause display defects such as image sticking. It was found to be a liquid crystal composition-containing liquid crystal composition.
  • Polymerizable compound-containing liquid crystal compositions of MLC-B1 (Comparative Example 4), MLC-B2 (Example 2), MLC-B3 (Example 3) and MLC-B4 (Example 4) were prepared and their physical properties were measured. Was measured. Table 3 shows the composition of the polymerizable compound-containing liquid crystal composition and the results of its physical property values.
  • MLC-B1 Comparative Example 4
  • MLC-B2 Example 2
  • MLC-B3 Example 3
  • MLC-B4 Example 4
  • ITO Indium Tin Oxide
  • UV irradiation was performed through a high-pressure mercury lamp through a filter that cuts off ultraviolet rays of 300 nm or less. At this time, the irradiation intensity on the cell surface was adjusted to 100 mW / cm 2 (365 nm).
  • PSVA liquid crystal display element in which the polymerizable compound in the polymerizable compound-containing liquid crystal composition was polymerized was obtained. All of these PSVA liquid crystal display elements exhibited an appropriate pretilt angle of about 88 °, and were confirmed to exhibit a response speed correlated with physical property values. For these PSVA liquid crystal display elements, VHR before and after UV irradiation and the amount of polymerizable compound remaining after UV irradiation were measured. The results are shown in Table 4.
  • the polymerizable compound-containing liquid crystal composition of the present invention MLC-B2 (Example 2), MLC-B3 (Example 3) and MLC-B4 (Example 4) have high UV resistance, and It was found that the polymerizable compound-containing liquid crystal composition has a small amount of the remaining polymerizable compound and does not cause display defects such as image sticking.
  • Polymeric compound-containing liquid crystal compositions of MLC-C1 (Comparative Example 5), MLC-C2 (Example 5), MLC-C3 (Example 6) and MLC-C4 (Example 7) were prepared, and their physical properties were measured. Was measured.
  • the composition of the polymerizable compound-containing liquid crystal composition and the results of its physical property values are shown in Table 5.
  • MLC-C1 Comparative Example 5
  • MLC-C2 Example 5
  • MLC-C3 Example 6
  • MLC-C4 Example 7
  • ITO Indium Tin Oxide
  • UV irradiation was performed through a high-pressure mercury lamp through a filter that cuts off ultraviolet rays of 300 nm or less. At this time, the irradiation intensity on the cell surface was adjusted to 100 mW / cm 2 (365 nm).
  • PSVA liquid crystal display element in which the polymerizable compound in the polymerizable compound-containing liquid crystal composition was polymerized was obtained. All of these PSVA liquid crystal display elements exhibited an appropriate pretilt angle of about 88 °, and were confirmed to exhibit a response speed correlated with physical property values. For these PSVA liquid crystal display elements, VHR before and after UV irradiation and the amount of polymerizable compound remaining after UV irradiation were measured. The results are shown in Table 6.
  • the polymerizable compound-containing liquid crystal composition of the present invention MLC-C2 (Example 5), MLC-C3 (Example 6) and MLC-C4 (Example 7) have high UV resistance, and It was found that the polymerizable compound-containing liquid crystal composition has a small amount of the remaining polymerizable compound and does not cause display defects such as image sticking.
  • Polymeric compound-containing liquid crystal compositions of MLC-D1 (Comparative Example 6), MLC-D2 (Example 8), MLC-D3 (Example 9) and MLC-D4 (Example 10) were prepared and their physical properties were measured. Was measured. Table 7 shows the composition of the polymerizable compound-containing liquid crystal composition and the results of its physical properties.
  • MLC-D1 Comparative Example 6
  • MLC-D2 Example 8
  • MLC-D3 Example 9
  • MLC-D4 Example 10
  • ITO ITO
  • UV irradiation was performed through a high-pressure mercury lamp through a filter that cuts off ultraviolet rays of 300 nm or less.
  • the irradiation intensity on the cell surface was adjusted to 100 mW / cm 2 (365 nm).
  • PSVA liquid crystal display element in which the polymerizable compound in the polymerizable compound-containing liquid crystal composition was polymerized was obtained. All of these PSVA liquid crystal display elements exhibited an appropriate pretilt angle of about 88 °, and were confirmed to exhibit a response speed correlated with physical property values. For these PSVA liquid crystal display elements, VHR before and after UV irradiation and the amount of polymerizable compound remaining after UV irradiation were measured. The results are shown in Table 8.
  • the polymerizable compound-containing liquid crystal composition of the present invention MLC-D2 (Example 8), MLC-D3 (Example 9) and MLC-D4 (Example 10) have high UV resistance, and It was found that the polymerizable compound-containing liquid crystal composition has a small amount of the remaining polymerizable compound and does not cause display defects such as image sticking.
  • Polymerizable compound-containing liquid crystal compositions of MLC-E1 (Comparative Example 7), MLC-E2 (Example 11), MLC-E3 (Example 12) and MLC-E4 (Example 13) were prepared, and their physical property values were prepared. Was measured. Table 9 shows the composition of the polymerizable compound-containing liquid crystal composition and the results of its physical property values.
  • MLC-E1 Comparative Example 7
  • MLC-E2 Example 11
  • MLC-E3 Example 12
  • MLC-E4 Example 13
  • ITO Indium Tin Oxide
  • UV irradiation was performed through a high-pressure mercury lamp through a filter that cuts off ultraviolet rays of 300 nm or less. At this time, the irradiation intensity on the cell surface was adjusted to 100 mW / cm 2 (365 nm).
  • PSVA liquid crystal display element in which the polymerizable compound in the polymerizable compound-containing liquid crystal composition was polymerized was obtained. All of these PSVA liquid crystal display elements exhibited an appropriate pretilt angle of about 88 °, and were confirmed to exhibit a response speed correlated with physical property values. For these PSVA liquid crystal display elements, VHR before and after UV irradiation and the amount of polymerizable compound remaining after UV irradiation were measured. The results are shown in Table 10.
  • the polymerizable compound-containing liquid crystal composition of the present invention MLC-E2 (Example 11), MLC-E3 (Example 12) and MLC-E4 (Example 13) have high UV resistance, and It was found that the polymerizable compound-containing liquid crystal composition has a small amount of the remaining polymerizable compound and does not cause display defects such as image sticking.
  • Polymerizable compound-containing liquid crystal compositions of MLC-F1 (Comparative Example 8), MLC-F2 (Example 14), MLC-F3 (Example 15) and MLC-F4 (Example 16) were prepared, and their physical property values were prepared. Was measured. Table 11 shows the composition of the polymerizable compound-containing liquid crystal composition and the results of its physical property values.
  • MLC-F1 Comparative Example 8
  • MLC-F2 Example 14
  • MLC-F3 Example 15
  • MLC-F4 Example 16
  • PSVA liquid crystal display element in which the polymerizable compound in the polymerizable compound-containing liquid crystal composition was polymerized was obtained. All of these PSVA liquid crystal display elements exhibited an appropriate pretilt angle of about 88 °, and were confirmed to exhibit a response speed correlated with physical property values. For these PSVA liquid crystal display elements, VHR before and after UV irradiation and the amount of polymerizable compound remaining after UV irradiation were measured. The results are shown in Table 12.
  • the polymerizable compound-containing liquid crystal composition of the present invention MLC-F2 (Example 14), MLC-F3 (Example 15) and MLC-F4 (Example 16) have high UV resistance, and It was found that the polymerizable compound-containing liquid crystal composition has a small amount of the remaining polymerizable compound and does not cause display defects such as image sticking.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Nonlinear Science (AREA)
  • Optics & Photonics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Mathematical Physics (AREA)
  • Liquid Crystal Substances (AREA)
  • Liquid Crystal (AREA)

Abstract

L'invention fournit une composition de cristaux liquides qui présente une viscosité （η） et une viscosité rotationnelle （γ１） suffisamment faibles, dont la vitesse de réaction d'un composé polymérisable est suffisamment rapide, et dont les résidus de composé polymérisable après irradiation aux UV sont nuls ou suffisamment restreints. Cette composition de cristaux liquides est avantageuse en ce qu'elle permet la fabrication d'un élément d'affichage à cristaux liquides de type à alignement durable de polymères, ou similaire, dont la vitesse de réponse est suffisamment rapide, qui est tel qu'une commande d'alignement uniforme et stable est obtenue à un coût énergétique faible, et simultanément, qui présente un rapport de maintien de tension (VHR) satisfaisant, et ne présente pas de risques d'apparition d'irrégularités d'affichage ni de brûlure, ou de manière extrêmement restreinte.
PCT/JP2016/079760 2015-10-16 2016-10-06 Composition de cristaux liquides nématiques, et élément d'affichage à cristaux liquides mettant en œuvre celle-ci Ceased WO2017065078A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN201680055198.0A CN108026449A (zh) 2015-10-16 2016-10-06 向列液晶组合物和使用其的液晶显示元件
JP2017545174A JPWO2017065078A1 (ja) 2015-10-16 2016-10-06 ネマチック液晶組成物及びこれを用いた液晶表示素子

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2015-204620 2015-10-16
JP2015204620 2015-10-16

Publications (1)

Publication Number Publication Date
WO2017065078A1 true WO2017065078A1 (fr) 2017-04-20

Family

ID=58518228

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2016/079760 Ceased WO2017065078A1 (fr) 2015-10-16 2016-10-06 Composition de cristaux liquides nématiques, et élément d'affichage à cristaux liquides mettant en œuvre celle-ci

Country Status (3)

Country Link
JP (1) JPWO2017065078A1 (fr)
CN (1) CN108026449A (fr)
WO (1) WO2017065078A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20170283698A1 (en) * 2016-03-31 2017-10-05 Jnc Corporation Liquid crystal composition and liquid crystal display device
JPWO2018043144A1 (ja) * 2016-09-01 2018-08-30 Dic株式会社 液晶表示素子
CN110317613A (zh) * 2018-03-28 2019-10-11 江苏和成显示科技有限公司 一种液晶组合物及液晶显示器件
CN110734770A (zh) * 2018-07-20 2020-01-31 Dic株式会社 液晶组合物和液晶显示元件

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI708832B (zh) * 2018-10-22 2020-11-01 達興材料股份有限公司 液晶組成物及使用此液晶組成物的液晶顯示裝置
CN109709704B (zh) * 2019-02-28 2022-11-11 京东方科技集团股份有限公司 调光玻璃及其制备方法
CN115975651A (zh) * 2022-12-07 2023-04-18 Tcl华星光电技术有限公司 液晶组合物、显示面板

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000119653A (ja) * 1998-10-16 2000-04-25 Dainippon Ink & Chem Inc ネマチック液晶組成物及びこれを用いた液晶表示装置
JP2001040354A (ja) * 1999-07-28 2001-02-13 Dainippon Ink & Chem Inc ネマチック液晶組成物及びこれを用いた液晶表示装置
JP2003193054A (ja) * 2001-12-27 2003-07-09 Chisso Corp 液晶組成物および液晶表示素子
JP2004137258A (ja) * 2002-09-27 2004-05-13 Dainippon Ink & Chem Inc １，７，８−トリフルオロ−２−ナフトール及びこれを用いた液晶化合物の製造方法
JP2012025667A (ja) * 2010-07-20 2012-02-09 Dic Corp フルオロナフタレン誘導体及びこれを含有する液晶組成物。
JP2015180728A (ja) * 2013-10-08 2015-10-15 Dic株式会社 ネマチック液晶組成物及びこれを用いた液晶表示素子

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2732765B2 (ja) * 1992-11-30 1998-03-30 シャープ株式会社 強誘電性液晶表示素子
CA2269561C (fr) * 1998-04-22 2007-06-05 Dainippon Ink And Chemicals, Inc. Derive de naphtalene et composition a cristaux liquides comprenant celui-ci
TWI319762B (en) * 2002-09-27 2010-01-21 1,7,8-trifluoro-2-naphthol and manufacturing methods for liquid crystal compositions containing the same
JP4941801B2 (ja) * 2004-08-27 2012-05-30 Ｄｉｃ株式会社 トリフルオロナフタレン誘導体を含有する液晶組成物と表示素子及び液晶性化合物、その製造法と製造中間体
WO2014148197A1 (fr) * 2013-03-21 2014-09-25 Dic株式会社 Composition de cristaux liquides contenant un composé polymérisable et élément d'affichage à cristaux liquides l'utilisant
CN103254907B (zh) * 2013-04-23 2016-01-20 石家庄诚志永华显示材料有限公司 负介电各向异性液晶组合物

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000119653A (ja) * 1998-10-16 2000-04-25 Dainippon Ink & Chem Inc ネマチック液晶組成物及びこれを用いた液晶表示装置
JP2001040354A (ja) * 1999-07-28 2001-02-13 Dainippon Ink & Chem Inc ネマチック液晶組成物及びこれを用いた液晶表示装置
JP2003193054A (ja) * 2001-12-27 2003-07-09 Chisso Corp 液晶組成物および液晶表示素子
JP2004137258A (ja) * 2002-09-27 2004-05-13 Dainippon Ink & Chem Inc １，７，８−トリフルオロ−２−ナフトール及びこれを用いた液晶化合物の製造方法
JP2012025667A (ja) * 2010-07-20 2012-02-09 Dic Corp フルオロナフタレン誘導体及びこれを含有する液晶組成物。
JP2015180728A (ja) * 2013-10-08 2015-10-15 Dic株式会社 ネマチック液晶組成物及びこれを用いた液晶表示素子

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20170283698A1 (en) * 2016-03-31 2017-10-05 Jnc Corporation Liquid crystal composition and liquid crystal display device
JPWO2018043144A1 (ja) * 2016-09-01 2018-08-30 Dic株式会社 液晶表示素子
CN110317613A (zh) * 2018-03-28 2019-10-11 江苏和成显示科技有限公司 一种液晶组合物及液晶显示器件
CN110317613B (zh) * 2018-03-28 2022-03-11 江苏和成显示科技有限公司 一种液晶组合物及液晶显示器件
CN110734770A (zh) * 2018-07-20 2020-01-31 Dic株式会社 液晶组合物和液晶显示元件

Also Published As

Publication number Publication date
CN108026449A (zh) 2018-05-11
JPWO2017065078A1 (ja) 2018-03-08

Similar Documents

Publication Publication Date Title
JP5678798B2 (ja) 重合性化合物含有液晶組成物及びそれを使用した液晶表示素子
JP5196073B2 (ja) 重合性化合物含有液晶組成物及びそれを使用した液晶表示素子
KR102117336B1 (ko) 네마틱 액정 조성물 및 이를 사용한 액정 표시 소자
JP6153999B2 (ja) 重合性化合物含有液晶組成物及びこれを使用した液晶表示素子
WO2017065078A1 (fr) Composition de cristaux liquides nématiques, et élément d'affichage à cristaux liquides mettant en œuvre celle-ci
WO2013161669A1 (fr) Composition de cristaux liquides comprenant un composé polymérisable, et dispositif d'affichage à cristaux liquides mettant en œuvre celle-ci
WO2013187373A1 (fr) Composition de cristaux liquides nématiques et élément d'affichage à cristaux liquides l'utilisant
JP2011162571A (ja) 重合性化合物を含有する液晶組成物及びそれを使用した液晶表示素子
WO2013161096A1 (fr) Composition de cristaux liquides nématiques, et dispositif d'affichage à cristaux liquides mettant en œuvre celle-ci
JP6369663B1 (ja) 液晶組成物及び液晶表示素子
JP6660560B2 (ja) ネマチック液晶組成物及びこれを用いた液晶表示素子
WO2015052948A1 (fr) Composition à cristaux liquides nématiques et éléments d'affichage à cristaux liquides l'utilisant
WO2013022088A1 (fr) Composition de cristaux liquides contenant un composé polymérisable et un élément d'affichage à cristaux liquides utilisant cette composition
WO2013175645A1 (fr) Composition de cristaux liquides nématiques et élément d'affichage à cristaux liquides l'utilisant
KR20180083308A (ko) 조성물 및 그것을 사용한 액정 표시 소자
JP5170602B1 (ja) ネマチック液晶組成物及びこれを用いた液晶表示素子
JP5565542B1 (ja) ネマチック液晶組成物及びこれを用いた液晶表示素子
WO2017098955A1 (fr) Composition, et élément d'affichage à cristaux liquides mettant en œuvre celle-ci
JP5170603B1 (ja) ネマチック液晶組成物及びこれを用いた液晶表示素子
JP6132122B2 (ja) 液晶組成物及びこれを用いた液晶表示素子
JP5582272B1 (ja) ネマチック液晶組成物及びこれを用いた液晶表示素子
JP2012082349A (ja) 重合性化合物含有液晶組成物及びそれを使用した液晶表示素子

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 16855332

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2017545174

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 16855332

Country of ref document: EP

Kind code of ref document: A1