WO2015029876A1 - ネマチック液晶組成物 - Google Patents
ネマチック液晶組成物 Download PDFInfo
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- WO2015029876A1 WO2015029876A1 PCT/JP2014/071903 JP2014071903W WO2015029876A1 WO 2015029876 A1 WO2015029876 A1 WO 2015029876A1 JP 2014071903 W JP2014071903 W JP 2014071903W WO 2015029876 A1 WO2015029876 A1 WO 2015029876A1
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- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- 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
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- 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
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- 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
- G02F1/13378—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by treatment of the surface, e.g. embossing, rubbing or light irradiation
- G02F1/133788—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by treatment of the surface, e.g. embossing, rubbing or light irradiation by light irradiation, e.g. linearly polarised light photo-polymerisation
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- C07C2601/14—The ring being saturated
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- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
- C09K2019/0466—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the linking chain being a -CF2O- chain
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- 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
- C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
- C09K2019/124—Ph-Ph-Ph-Ph
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- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3025—Cy-Ph-Ph-Ph
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- G02F1/0045—Liquid crystals characterised by their physical properties
Definitions
- the present invention relates to a nematic liquid crystal composition having a positive dielectric anisotropy ( ⁇ ) useful as an electro-optical liquid crystal display material.
- Liquid crystal display elements are used in various measuring instruments, automobile panels, word processors, electronic notebooks, printers, computers, televisions, watches, advertisement display boards, etc., including clocks and calculators.
- Typical liquid crystal display methods include TN (twisted nematic) type, STN (super twisted nematic) type, VA type characterized by vertical alignment using TFT (thin film transistor) and horizontal alignment.
- the liquid crystal composition used in these liquid crystal display elements is stable against external factors such as moisture, air, heat, light, etc., and exhibits a liquid crystal phase in the widest possible temperature range centering on room temperature, and has low viscosity. And a low driving voltage is required.
- the liquid crystal composition has several to several tens of kinds of compounds in order to optimize the dielectric anisotropy ( ⁇ ) and the refractive index anisotropy ( ⁇ n) for each display element. It is composed of
- a liquid crystal composition having a negative ⁇ is used for a vertical alignment type display
- a liquid crystal composition having a positive ⁇ is used for a horizontal alignment type display such as a TN type, STN type, or IPS type.
- a driving method has been reported in which a liquid crystal composition having a positive ⁇ is vertically aligned when no voltage is applied and an IPS type / FFS type electric field is applied, and the necessity of a liquid crystal composition having a positive ⁇ is reported. Is growing further. On the other hand, low voltage driving, high-speed response, and a wide operating temperature range are required in all driving systems.
- ⁇ is positive, the absolute value is large, the viscosity ( ⁇ ) is small, and a high nematic phase-isotropic liquid phase transition temperature (T ni ) is required.
- T ni nematic phase-isotropic liquid phase transition temperature
- An object of the present invention is to solve is adjusted to a desired refractive index anisotropy ([Delta] n), nematic phase - suppress reduction and increase of the minimum temperature of a nematic phase of isotropic liquid phase transition temperature (T ni)
- a liquid crystal composition having a sufficiently low viscosity ( ⁇ ) and a positive dielectric anisotropy ( ⁇ ) without deteriorating the temperature range of the nematic phase.
- the present inventor has studied various fluorobenzene derivatives and found that the above problem can be solved by combining specific compounds, and has completed the present invention.
- the present invention is a liquid crystal composition having positive dielectric anisotropy, wherein the liquid crystal composition contains one or more compounds represented by the general formula (LC0).
- a composition is provided, and a liquid crystal display element using the liquid crystal composition is further provided.
- R 01 represents an alkyl group having 1 to 15 carbon atoms, and one or two or more —CH 2 — in the alkyl group is —O—, —
- One or more of the alkyl groups may be substituted with CH ⁇ CH—, —CO—, —OCO—, —COO—, —C ⁇ C—, —CF 2 O— or —OCF 2 —.
- the hydrogen atom of may be optionally substituted with halogen
- a 01 to A 03 each independently represent one of the following structures:
- —CH 2 — in the cyclohexane ring in the structure may be substituted with —O— so that the oxygen atom is not directly adjacent, and one or two of the benzene rings in the structure
- —CH ⁇ may be substituted with —N ⁇ so that the nitrogen atom is not directly adjacent to each other, and X 03 and X 04 are each independently —H, —Cl, —F, —CF 3 or — Represents OCF 3
- the partial structural formula (LC0-Ph) in the formula can also be the formula (LC0-Np)
- X 01 , X 02 and X 05 each independently represent a hydrogen atom or a fluorine atom
- Y 01 represents —Cl, —F, —OCHF 2 , —CF 3 , —OCF 3 , a fluorinated alkyl group having 2 to 5 carbon atoms, an alkoxy group, an alkenyl group or an alkenyloxy group
- Z 01 to Z 05 are each independently a single bond, —CH ⁇ CH—, —C ⁇ C—, —CH 2 CH 2 —, — (CH 2 ) 4 —, —OCH 2 —, —CH 2 O—.
- Z 01 ⁇ Z 05 present is -OCH 2 -
- - OCF 2 - or -CF 2 is O-
- W 01 and W 02 each independently represent —CH 2 — or —O—
- m 01 to m 03 each independently represents an integer of 0 to 2
- m 01 + m 02 + m 03 represents 0, 1 or 2
- the liquid crystal composition of the present invention is characterized in that ⁇ is positive and its absolute value can be increased. Also, ⁇ is low, rotational viscosity ( ⁇ 1 ) is small, liquid crystallinity is excellent, and a stable liquid crystal phase is exhibited over a wide temperature range. In addition, it is chemically stable to heat, light, water, etc., has good solubility, has good phase stability at low temperature, and can be driven at low voltage. It is a thing.
- the liquid crystal composition of the present invention has the general formula (LC0)
- R 01 is preferably an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms, and is preferably linear. preferable.
- R 01 is an alkenyl group, it is preferably selected from groups represented by any one of formulas (R1) to (R5). (The black dot in each formula represents the point of connection with the ring.)
- a 01 is a trans-1,4-cyclohexylene group, these are preferred, and the formula (R1), formula (R2), and formula (R4) are Further preferred.
- a 01 to A 03 are each independently a trans-1,4-cyclohexylene group, 1,4-phenylene group, 3-fluoro-1,4-phenylene group or 3,5-difluoro-1,4-phenylene.
- Groups and tetrahydropyran groups are preferred. In this case, it is preferable to contain one or more compounds selected from the group of these compounds in order to solve the problems of the present invention.
- the partial structural formula (LC0-Ph) in the formula can also be the formula (LC0-Np).
- X 01 , X 02 and X 05 each independently represents a hydrogen atom or a fluorine atom
- Y 01 represents —Cl, —F, —OCHF 2 , —CF 3 , —OCF 3 , a fluorinated alkyl group having 2 to 5 carbon atoms, an alkoxy group, an alkenyl group, or an alkenyloxy group.
- X 01 to X 05 are preferably F because they have a significantly low viscosity ( ⁇ ) with respect to a large dielectric anisotropy ( ⁇ ) or a comparable dielectric anisotropy ( ⁇ ).
- the number of F substitutions is preferably 2 to 7, including the two already described in the general formula (LC0).
- n 01 to m 03 can each independently represent an integer of 0 to 2, but it is particularly preferable to use a compound in which m 01 + m 02 + m 03 is 0 and a compound of 1 in combination.
- the compound represented by the general formula (LC0) is preferably a compound satisfying at least one of the following matters.
- m 01 is 1.
- m 01 is 2, and one Z 01 is A compound in which —OCH 2 —, —OCF 2 — or —CF 2 O— and the other Z 01 is a single bond • m 02 is 1 or 2, and one of Z 02 and Z 03 is —OCH 2 —, —OCF 2 — or —CF 2 O—, wherein the remaining Z 02 and Z 03 are a single bond.
- M 03 is 1 or 2, and one of Z 04 and Z 05 is — A compound in which OCH 2 —, —OCF 2 — or —CF 2 O—, and the remaining Z 04 and Z 05 are a single bond
- the liquid crystal compounds represented by C0) are represented by the following general formulas (LC0-a) to (LC0-d) (In the formula, R 01 , A 01 to A 03 , Z 01 to Z 05 , X 01 , X 02 and Y 01 represent the same meanings in the general formula (LC0), and are the same when two or more exist. Or may be different.) Is more preferable.
- the liquid crystal composition of the present invention preferably contains one or more compounds represented by (LC0-a) to (LC0-d) as the compound represented by the general formula (LC0).
- the compound represented by the general formula (LC0) is more preferably a compound represented by the following general formula (LC0-1) to general formula (LC0-74).
- the compounds represented by the general formulas (LC0-1) to (LC0-9) have a large dielectric anisotropy ( ⁇ ) and a remarkably low viscosity ( ⁇ ) and at the same time have excellent compatibility. Is particularly preferred.
- the compounds represented by the general formulas (LC0-10) to (LC0-67) have a large dielectric anisotropy ( ⁇ ) and a relatively low viscosity ( ⁇ ) and at the same time a high nematic phase-isotropic property. It is particularly preferable because it has a liquid phase transition temperature (T ni ).
- liquid crystal composition containing the compound represented by the general formula (LC0) it is more preferable to satisfy at least one of the following matters.
- General formula (LC0-60) A compound represented by the general formula (LC0-67) Therefore, it is a compound represented by general formula (LC0-68) to general formula (LC0-74) and contains at most 15 mass%.
- General formula (LC0-2) General formula (LC0-5), general formula (LC0-7), general formula (LC0-11) to general formula (LC0-15), general formula (LC0-17), general formula (LC0-18), general Formula (LC0-20), Formula (LC0-28) to Formula (LC0-30), Formula (LC0-34), Formula (LC0-35), Formula (LC0-39), Formula (LC LC0-41), general formula (LC0-45), general formula (LC0-46), general formula (LC0-56) to general formula (LC0-61), general formula (LC0-68) or general formula (LC0- 74)
- One or more compounds selected from the group of compounds represented by 74) contains
- R 01 is an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms
- the liquid crystal composition further contains one or more compounds selected from a compound group represented by formulas (LC1) to (LC5).
- a liquid crystal composition including one or more compounds represented by the general formula (LC0) and satisfying at least one of the following matters is preferable.
- ⁇ Contains at most 20 mass% of the compound represented by the general formula (LC1) ⁇ Contains at most 40 mass% of the compound represented by the general formula (LC2) ⁇ Contains the compound represented by the general formula (LC3) Contains at most 50% by mass-Contains at most 60% by mass of the compound represented by the general formula (LC4) -Contains at most 75% by mass of the compound represented by the general formula (LC5)
- R 11 to R 41 each independently represents an alkyl group having 1 to 15 carbon atoms, and one or more of —CH 2 — in the alkyl group is not directly adjacent to an oxygen atom. May be substituted with —O—, —CH ⁇ CH—, —CO—, —OCO—, —COO—, —C ⁇ C—, —CF 2 O— or —OCF 2 —.
- R 51 and R 52 each independently represents an alkyl group having 1 to 15 carbon atoms, and one of the alkyl groups Or two or more —CH 2 — are substituted with —O—, —CH ⁇ CH—, —CO—, —OCO—, —COO— or —C ⁇ C— so that the oxygen atom is not directly adjacent.
- a 11 ⁇ A 42 are each independently either the following structures
- —CH 2 CH 2 — in the cyclohexane ring may be substituted with —CH ⁇ CH—, —CF 2 O— or —OCF 2 —
- X 11 to X 43 each independently represent —H, —Cl , -F, -CF 3 or -OCF 3
- Y 11 to Y 41 are -Cl, -F, -CF 3 , -OCF 3 , -CF 2 CF 3 , -CHFCF 3 , -OCF 2 CF 3 , —OCHFCF 3 or —OCF ⁇ CF 2
- Z 31 to Z 42 are each independently a single bond, —CH ⁇ CH—, —C ⁇ C—, —CH 2 CH 2 —, — (CH 2 ) 4 -, - OCH 2 -, - CH 2
- R 11 to R 41 each independently represents an alkyl group having 1 to 15 carbon atoms, and one or two or more —CH in the alkyl group 2 — means —O—, —CH ⁇ CH—, —CO—, —OCO—, —COO—, —C ⁇ C—, —CF 2 O— or —OCF 2 so that oxygen atoms are not directly adjacent to each other.
- 1 or 2 or more hydrogen atoms in the alkyl group may be optionally substituted with halogen, but may be an alkyl group having 1 to 8 carbon atoms, alkenyl having 2 to 8 carbon atoms Or an alkoxy group having 1 to 8 carbon atoms, preferably a straight chain, and R 51 and R 52 each independently represents an alkyl group having 1 to 15 carbon atoms, One or more —CH 2 — is directly adjacent to an oxygen atom May be substituted with —O—, —CH ⁇ CH—, —CO—, —OCO—, —COO— or —C ⁇ C—, but an alkyl group having 1 to 8 carbon atoms, 2 carbon atoms An alkenyl group having 8 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms is preferable, and a straight chain is preferable.
- R 11 to R 52 are alkenyl groups, they are preferably selected from groups represented by any one of formulas (R1) to (R5)
- a 11 to A 42 are each independently a trans-1,4-cyclohexylene group, 1,4-phenylene group, 3-fluoro-1,4-phenylene group, or 3,5-difluoro-1,4-phenylene group. Or a tetrahydropyran group is preferable. When A 11 to A 42 include a tetrahydropyran group, A 11 , A 21 and A 31 are preferable.
- a 51 to A 53 are each independently preferably a trans-1,4-cyclohexylene group, a 1,4-phenylene group, a 2-fluoro-1,4-phenylene group or a 3-fluoro-1,4-phenylene group. .
- X 11 to X 43 are preferably each independently a hydrogen atom or a fluorine atom.
- Y 11 to Y 41 are preferably —F, —CF 3 or —OCF 3 .
- Z 31 to Z 42 are each independently a single bond, —CH ⁇ CH—, —C ⁇ C—, —CH 2 CH 2 —, — (CH 2 ) 4 —, —OCH 2 —, —CH 2 O—.
- —OCF 2 — or —CF 2 O— is preferred, and at least one of Z 31 and Z 32 present is not a single bond.
- Z 41 each independently represents a single bond, —CH ⁇ CH—, —C ⁇ C—, —CH 2 CH 2 — or — (CH 2 ) 4 —.
- Z 51 and Z 52 are each independently a single bond, —CH ⁇ CH—, —C ⁇ C—, —CH 2 CH 2 —, — (CH 2 ) 4 —, —OCH 2 —, —CH 2 O—.
- m 21 preferably represents an integer of 0 or 1.
- m 31 to m 42 each independently preferably represents an integer of 0 to 2
- m 31 + m 32 and m 41 + m 42 each independently preferably represents 1, 2 or 3.
- m 51 preferably represents an integer of 1 or 2.
- R 11 represents an alkyl group having 1 to 15 carbon atoms, and one or more of —CH 2 — in the alkyl group is —O—, — One or more of the alkyl groups may be substituted with CH ⁇ CH—, —CO—, —OCO—, —COO—, —C ⁇ C—, —CF 2 O— or —OCF 2 —.
- X 11 and X 12 each independently represents —H, —Cl, —F, —CF 3 or —OCF 3
- R 21 represents an alkyl group having 1 to 15 carbon atoms, and one or two or more —CH 2 — in the alkyl group is —O—, — One or more of the alkyl groups may be substituted with CH ⁇ CH—, —CO—, —OCO—, —COO—, —C ⁇ C—, —CF 2 O— or —OCF 2 —.
- X 22 to X 26 each independently represents —H, —Cl, —F, —CF 3 or —OCF 3
- X 22 to X 26 each independently represents —H, —Cl, —F, —CF 3 or —OCF 3
- the compound represented by the general formula (LC3) is a group of compounds represented by the general formula (LC3-1) to the general formula (LC3-32) and / or the general formula (LC3-0-1) to the general formula (LC3- 0-97)
- R represents the same meaning as R 31 in formula (LC3), and X 33 , X 34 , X 35 , X 36 , X 37 and X 38 are each independently H, Cl, F, CF 3.
- OCF 3 , X 32 , R 31 , R 31 represents an alkyl group having 1 to 15 carbon atoms, and one or more of —CH 2 — in the alkyl group is directly adjacent to an oxygen atom
- the alkyl may be substituted with —O—, —CH ⁇ CH—, —CO—, —OCO—, —COO—, —C ⁇ C—, —CF 2 O— or —OCF 2 —
- One or more hydrogen atoms in the group may be optionally substituted with halogen
- X 32 represents —H, —Cl, —F, —CF 3 or —OCF 3
- Y 31 represents — Cl, -F, -CF 3, -OCF 3, -CF 2 CF 3,
- R 41 represents an alkyl group having 1 to 15 carbon atoms, One or more —CH 2 — in the group is —O—, —CH ⁇ CH—, —CO—, —OCO—, —COO—, —C ⁇ so that the oxygen atom is not directly adjacent.
- C -, - CF 2 O- or -OCF 2 - may be substituted with, one or more hydrogen atoms in the alkyl group may be optionally substituted with halogen, X 42, X 43
- X 42, X 43 Each independently represents —H, —Cl, —F, —CF 3 or —OCF 3
- Y 41 represents —Cl, —F, —CF 3 , —OCF 3 , —CF 2 CF 3 , —CHFCF 3 , —OCF 2 CF 3 , —OCHFCF 3 or —OCF ⁇ CF 2 ) It is preferable that it is a compound represented.
- R 51 and R 52 each independently represent an alkyl group having 1 to 15 carbon atoms, and one or two or more —CH 2 — in the alkyl group is not directly adjacent to an oxygen atom. In addition, it may be substituted with —O—, —CH ⁇ CH—, —CO—, —OCO—, —COO—, or —C ⁇ C—.
- the liquid crystal composition of the present invention preferably contains one or more compounds represented by the general formula (LC5), preferably 20 to 80% by mass, and 30 to 70% by mass. It is more preferable that
- alkyl and alkyl * each independently represent an alkyl group or alkoxy group having 1 to 5 carbon atoms
- alkylyl and alkenyl * each independently represent an alkenyl group or alkenyloxy group having 2 to 5 carbon atoms in the following formulae. Represents a group.
- the liquid crystal composition of the present invention preferably has a viscosity ⁇ at 20 ° C. of 20 mPa ⁇ s or less.
- the liquid crystal composition of the present invention can contain one or more optically active compounds. Any optically active compound can be used as long as the liquid crystal molecules can be twisted and aligned. Usually, since this twist changes with temperature, a plurality of optically active compounds can be used to obtain a desired temperature dependency. In order not to adversely affect the temperature range and viscosity of the nematic liquid crystal phase, it is preferable to select and use an optically active compound having a strong twisting effect.
- a liquid crystal such as cholesteric nonanate or a compound represented by the following general formulas (Ch-1) to (Ch-6) is preferably contained.
- R c1 , R c2 , and R * each independently represents an alkyl group having 1 to 15 carbon atoms, and one or two or more —CH 2 — in the alkyl group has a direct oxygen atom May be substituted with —O—, —CH ⁇ CH—, —CO—, —OCO—, —COO—, —C ⁇ C—, —CF 2 O— or —OCF 2 — so as not to be adjacent,
- One or more hydrogen atoms in the alkyl group may be optionally substituted with halogen, provided that R * has at least one branched or halogen substituent having optical activity
- Z c1 , Z c2 each independently a single bond, —CH ⁇ CH—, —C ⁇ C—, —CH 2 CH 2 —, — (CH 2 ) 4 —, —COO—, —OCO—, —OCH 2 -, - CH 2 O -, - OCF 2 - or
- D 3 and D 4 represent a cyclohexane ring or a benzene ring, and one or more of —CH 2 — in the cyclohexane ring is substituted with —O— so that the oxygen atom is not directly adjacent.
- one or more of —CH 2 CH 2 — in the ring note may be substituted with —CH ⁇ CH—, —CF 2 O— or —OCF 2 —.
- One or more —CH ⁇ may be substituted with —N ⁇ so that the nitrogen atoms are not directly adjacent, and one or more hydrogen atoms in the ring are substituted with F, Cl, CH 3 May be used).
- the liquid crystal composition of the present invention may contain one or more polymerizable compounds, and the polymerizable compound contains a benzene derivative, a triphenylene derivative, a truxene derivative, a phthalocyanine derivative or a cyclohexane derivative at the center of the molecule. And a discotic liquid crystal compound having a structure in which a linear alkyl group, a linear alkoxy group or a substituted benzoyloxy group is radially substituted as its side chain.
- the polymerizable compound is represented by the general formula (PC)
- P 1 represents a polymerizable functional group
- Sp 1 represents a spacer group having 0 to 20 carbon atoms
- Q p1 represents a single bond, —O—, —NH—, —NHCOO—, —OCONH— , —CH ⁇ CH—, —CO—, —COO—, —OCO—, —OCOO—, —OOCO—, —CH ⁇ CH—, —CH ⁇ CH—COO—, —OCO—CH ⁇ CH— or — C ⁇ C—
- p 1 and p 2 each independently represent 1, 2 or 3
- MG p represents a mesogenic group or a mesogenic support group
- R p1 represents a halogen atom, a cyano group or a carbon atom Represents an alkyl group of 1 to 25, and one or more CH 2 groups in the alkyl group are —O—, —S—, —NH—
- MG p in the polymerizable compound general formula (PC) has the following structure:
- C 01 to C 03 are each independently 1,4-phenylene group, 1,4-cyclohexylene group, 1,4-cyclohexenyl group, tetrahydropyran-2,5-diyl group, 1,3 -Dioxane-2,5-diyl group, tetrahydrothiopyran-2,5-diyl group, 1,4-bicyclo (2,2,2) octylene group, decahydronaphthalene-2,6-diyl group, pyridine-2 , 5-diyl group, pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 2,6-naphthylene group, phenanthrene -2,7-diyl group, 9,10-dihydrophenanthrene-2,7
- Z p1 and Z p2 are each independently —COO—, —OCO—, —CH 2 CH 2 —, —OCH 2 —, —CH 2 O—, —CH ⁇ CH—, —C ⁇ C—.
- -CH CHCOO -
- - OCOCH CH -, - CH 2 CH 2 COO -, - CH 2 CH 2 OCO -, - COOCH 2 CH 2 -, - OCOCH 2 CH 2 -, - CONH -, - NHCO- Or a single bond
- 3 represents 0, 1 or 2.
- Sp 1 and Sp 2 are each independently an alkylene group
- the alkylene group may be substituted by one or more halogen atoms or CN, and one or two present in the group
- the above CH 2 groups are —O—, —S—, —NH—, —N (CH 3 ) —, —CO—, —COO—, —OCO—, —
- R p2 to R p6 each independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 5 carbon atoms.
- PC polymerizable compound general formula
- p 4 are each independently represents 1, 2 or 3.
- Sp 1 , Sp 2 , Q p1 and Q p2 are preferably a single bond
- P 1 and P 2 are preferably the formula (PC0-a), and are an acryloyloxy group and a methacryloyloxy group. More preferably, p 1 + p 4 is preferably 2, 3 or 4, and R p1 is preferably H, F, CF 3 , OCF 3 , CH 3 or OCH 3 .
- compounds represented by general formula (PC1-2), general formula (PC1-3), general formula (PC1-4) and general formula (PC1-8) are preferred.
- MG p in the general formula (PC) is a discotic liquid crystal compound represented by the general formula (PC1) -9.
- R 7 independently represents P 1 -Sp 1 -Q p 1 or a substituent of the general formula (PC1-e), and R 81 and R 82 each independently represents a hydrogen atom, a halogen atom or methyl
- R 83 represents an alkoxy group having 1 to 20 carbon atoms, and at least one hydrogen atom in the alkoxy group is a substituent represented by the general formulas (PC0-a) to (PC0-d). Has been replaced.
- the amount of the polymerizable compound used is preferably 0.05 to 2.0% by mass.
- the liquid crystal composition containing the polymerizable compound of the present invention is prepared by polymerizing the polymerizable compound. At this time, it is required to reduce the unpolymerized component to a desired amount or less, and the liquid crystal composition contains a compound having a biphenyl group and / or a terphenyl group in the partial structure in the general formula (LC0).
- the compound represented by -68) is preferable, and one or more compounds are preferably selected and contained in an amount of 0.1 to 40% by mass. Further, they can be used together in the group consisting of polymerizable compounds represented by the general formula (PC1-1) to the general formula (PC1-3), the general formula (PC1-8) or the general formula (PC1-9). preferable.
- the liquid crystal composition may further contain one or more antioxidants, and may further contain one or more UV absorbers.
- the antioxidant is preferably selected from those represented by the following general formula (E-1) and / or general formula (E-2).
- R e1 represents an alkyl group having 1 to 15 carbon atoms, and one or two or more —CH 2 — in the alkyl group is —O—, —
- One or more of the alkyl groups may be substituted with CH ⁇ CH—, —CO—, —OCO—, —COO—, —C ⁇ C—, —CF 2 O— or —OCF 2 —.
- the hydrogen atom of may be optionally substituted with halogen
- Z e1 and Z e2 are each independently a single bond, —CH ⁇ CH—, —C ⁇ C—, —CH 2 CH 2 —, — (CH 2 ) 4 —, —COO—, —OCO—, —OCH 2 —, —CH 2 O—, —OCF 2 — or —CF 2 O—
- E 1 represents a cyclohexane ring or a benzene ring
- one or more —CH 2 — in the cyclohexane ring represents an oxygen atom May be substituted with —O— so that they are not directly adjacent to each other
- one or more —CH 2 CH 2 — in the ring note may be —CH ⁇ CH—, —CF 2 O— or —OCF 2 - as can be substituted
- one or more -CH nitrogen atom in the benzene ring are not directly adjacent with may be substituted
- the liquid crystal composition of the present invention can be used as a liquid crystal display element, particularly an active matrix driving liquid crystal display element, for example, TN mode, OCB mode, ECB mode, IPS (including FFS electrode) mode or VA-IPS mode (including FFS electrode).
- TN mode for example, TN mode, OCB mode, ECB mode, IPS (including FFS electrode) mode or VA-IPS mode (including FFS electrode).
- VA-IPS mode refers to a pixel electrode arranged on the same substrate surface by aligning a liquid crystal material ( ⁇ > 0) having a positive dielectric anisotropy perpendicular to the substrate surface when no voltage is applied. This is a method of driving liquid crystal molecules by a common electrode.
- Vc threshold voltage
- the VA method is expressed by the following equation.
- Vc is the Frederick transition (V)
- ⁇ is the circumference
- d cell is the distance between the first substrate and the second substrate ( ⁇ m)
- d gap is the distance between the pixel electrode and the common electrode ( ⁇ m)
- d ITO is the pixel electrode and / or common electrode width ( ⁇ m)
- ⁇ r1>, ⁇ r2>, and ⁇ r3> are extrapolated lengths ( ⁇ m)
- K11 is the spray elastic constant (N)
- K22 is the twist elasticity.
- Constant (N) represents the elastic constant (N) of the bend
- ⁇ represents the anisotropy of the dielectric constant.
- the present invention has found that the following formula 4 is applied.
- Vc is the Frederick transition (V)
- ⁇ is the circumference
- d cell is the distance between the first substrate and the second substrate ( ⁇ m)
- d gap is the distance between the pixel electrode and the common electrode ( ⁇ m)
- d ITO is the width of the pixel electrode and / or common electrode ( ⁇ m)
- ⁇ r>, ⁇ r ′>, ⁇ r3> are extrapolation lengths ( ⁇ m)
- K33 is the bend elastic constant (N)
- ⁇ is the dielectric constant represents the anisotropy.
- the cell configuration of several 4 the d gap as small as possible, by as large as possible a d ITO, lower driving voltage is Hakare large absolute value of ⁇ is the liquid crystal composition used , K33 can be selected to reduce the drive voltage.
- the liquid crystal display element produced using the liquid crystal composition of the present invention can be produced by rubbing treatment using polyimide or polyamide compound as a method for aligning liquid crystal molecules on the substrate surface. It can also be produced by a photo-alignment technique using chalcone, cinnamate, cinnamoyl compound or the like. Further, as a new alignment method, a method in which a polymerizable liquid crystal compound is incorporated in the alignment layer and the polymerizable liquid crystal compound is polymerized can also be applied.
- the liquid crystal composition of the present invention can adjust preferable ⁇ , K11, K33 and the like.
- the product ( ⁇ n ⁇ d) of the refractive index anisotropy ( ⁇ n) of the liquid crystal composition and the distance (d) between the first substrate and the second substrate of the display device is strongly related to viewing angle characteristics and response speed. . Therefore, the interval (d) tends to be as thin as 3 to 4 ⁇ m.
- the product ( ⁇ n ⁇ d) is particularly preferably 0.31 to 0.33 in the case of the TN, ECB, IPS (liquid crystal alignment without application is substantially horizontal to the substrate surface) method. In the VA-IPS system, 0.20 to 0.59 is preferable for the vertical alignment with respect to both substrates, and 0.30 to 0.40 is particularly preferable.
- the refractive index anisotropy ( ⁇ n) of the liquid crystal composition suitable for each mode is 0.070 to 0.110.
- the liquid crystal composition of the present invention containing a compound represented by the general formula (PC) as a polymerizable compound was prepared by polymerizing a polymerizable compound contained in the liquid crystal composition with or without voltage application.
- a liquid crystal display element for TN mode, OCB mode, ECB mode, IPS mode or VA-IPS mode of polymer stabilization can be provided.
- a liquid crystal composition containing a polymerizable compound is sandwiched between two substrates, and the polymerizable compound in the liquid crystal composition is polymerized by energy such as ultraviolet rays with or without voltage applied. Can be produced.
- the orientation state of the liquid crystal molecules can be memorized by polymerizing the polymerizable compound, whereby the stability of the orientation state can be improved. In addition, an improvement in response speed can be expected.
- T NI Nematic phase-isotropic liquid phase transition temperature (° C)
- Tn lower limit temperature of nematic phase (° C)
- ⁇ dielectric constant in the direction perpendicular to the molecular long axis direction at 25 ° C.
- ⁇ dielectric anisotropy at 25 ° C. no: refractive index for ordinary light at 25 ° C.
- ⁇ n refractive index anisotropic at 25 ° C.
- sex Vth Applied voltage (V) in a cell having a cell thickness of 6 ⁇ m in which the transmittance changes by 10% when a rectangular wave with a frequency of 1 KHz is applied at 25 ° C.
- ⁇ 20 Bulk viscosity at 20 ° C. (mPa ⁇ s)
- ⁇ 1 rotational viscosity (mPa ⁇ s)
- the following abbreviations are used in compound descriptions.
- Example 1 (Comparative Example 1) The prepared liquid crystal composition and its physical property values are shown below.
- Ex-1 is a liquid crystal composition containing the compound represented by the general formula (LC0) of the present application
- Ref-1 is a liquid crystal composition not containing the compound represented by the general formula (LC0) of the present application.
- the ⁇ 1 of Ex-1 was 74 mPa ⁇ s
- the ⁇ 1 of Ref- 1 was 96 mPa ⁇ s.
- Example 1 has a much lower viscosity and the combination of the present invention is very excellent. I know that there is.
- Example 2 The liquid crystal composition composed of the compound of the general formula (LC5) and its physical property values are shown below.
- liquid crystal compositions prepared using Mix-A and Mix-B and their physical properties are shown.
- Example 3 The prepared liquid crystal composition and its physical property values are shown below.
- Example 4 The prepared liquid crystal composition and its physical property values are shown below.
- Example 5 The prepared liquid crystal composition and its physical property values are shown below.
- Example 6 The prepared liquid crystal composition and its physical property values are shown below.
- Example 7 The prepared liquid crystal composition and its physical property values are shown below.
- Example 8 The prepared liquid crystal composition and its physical property values are shown below.
- Example 9 The prepared liquid crystal composition and its physical property values are shown below.
- Example 10 The prepared liquid crystal composition and its physical property values are shown below.
- Example 11 The prepared liquid crystal composition and its physical property values are shown below.
- Example 12 The prepared liquid crystal composition and its physical property values are shown below.
- Example 13 The prepared liquid crystal composition and its physical property values are shown below.
- Example 14 The prepared liquid crystal composition and its physical property values are shown below.
- Example 15 The prepared liquid crystal composition and its physical property values are shown below.
- Example 16 The prepared liquid crystal composition and its physical property values are shown below.
- Example 17 The prepared liquid crystal composition and its physical property values are shown below.
- Example 18 The prepared liquid crystal composition and its physical property values are shown below.
- Example 19 The prepared liquid crystal composition and its physical property values are shown below.
- Example 20 The prepared liquid crystal composition and its physical property values are shown below.
- Example 21 The prepared liquid crystal composition and its physical property values are shown below.
- Example 22 The prepared liquid crystal composition and its physical property values are shown below.
- Example 23 The prepared liquid crystal composition and its physical property values are shown below.
- Example 24 The prepared liquid crystal composition and its physical property values are shown below.
- Example 25 The prepared liquid crystal composition and its physical property values are shown below.
- Example 26 The prepared liquid crystal composition and its physical property values are shown below.
- Example 27 The prepared liquid crystal composition and its physical property values are shown below.
- Example 28 The prepared liquid crystal composition and its physical property values are shown below.
- Example 29 The prepared liquid crystal composition and its physical property values are shown below.
- Example 30 The prepared liquid crystal composition and its physical property values are shown below.
- Example 31 The prepared liquid crystal composition and its physical property values are shown below.
- Example 32 The prepared liquid crystal composition and its physical property values are shown below.
- Example 33 The prepared liquid crystal composition and its physical property values are shown below.
- Example 34 The prepared liquid crystal composition and its physical property values are shown below.
- Example 35 The prepared liquid crystal composition and its physical property values are shown below.
- Example 36 The prepared liquid crystal composition and its physical property values are shown below.
- Example 37 The prepared liquid crystal composition and its physical property values are shown below.
- Example 38 The prepared liquid crystal composition and its physical property values are shown below.
- Example 39 The prepared liquid crystal composition and its physical property values are shown below.
- Example 40 The prepared liquid crystal composition and its physical property values are shown below.
- Example 41 The prepared liquid crystal composition and its physical property values are shown below.
- Example 42 The prepared liquid crystal composition and its physical property values are shown below.
- Example 43 The prepared liquid crystal composition and its physical property values are shown below.
- Example 44 The prepared liquid crystal composition and its physical property values are shown below.
- Example 45 The prepared liquid crystal composition and its physical property values are shown below.
- Example 46 The prepared liquid crystal composition and its physical property values are shown below.
- Example 47 The prepared liquid crystal composition and its physical property values are shown below.
- Example 48 The prepared liquid crystal composition and its physical property values are shown below.
- Example 49 The prepared liquid crystal composition and its physical property values are shown below.
- Example 50 The prepared liquid crystal composition and its physical property values are shown below.
- Example 51 The prepared liquid crystal composition and its physical property values are shown below.
- Example 52 The prepared liquid crystal composition and its physical property values are shown below.
- Example 53 The prepared liquid crystal composition and its physical property values are shown below.
- Example 54 The prepared liquid crystal composition and its physical property values are shown below.
- Example 55 The prepared liquid crystal composition and its physical property values are shown below.
- Example 56 The prepared liquid crystal composition and its physical property values are shown below.
- Example 57 The prepared liquid crystal composition and its physical property values are shown below.
- Example 58 The prepared liquid crystal composition and its physical property values are shown below.
- Example 59 The prepared liquid crystal composition and its physical property values are shown below.
- Example 60 The prepared liquid crystal composition and its physical property values are shown below.
- Example 61 The prepared liquid crystal composition and its physical property values are shown below.
- Example 62 The prepared liquid crystal composition and its physical property values are shown below.
- Example 63 The prepared liquid crystal composition and its physical property values are shown below.
- Example 64 The prepared liquid crystal composition and its physical property values are shown below.
- Example 65 The prepared liquid crystal composition and its physical property values are shown below.
- Example 66 The physical properties of ⁇ 1 at 20 ° C. in the liquid crystal composition of the present invention are shown below.
- the liquid crystal composition of the invention, gamma 1 is relatively small relative to the size of the dielectric anisotropy ([Delta] [epsilon]), it can be seen that the combination of the present invention is that excellent.
- Example 9 46 mPa ⁇ s ⁇ 1 of Example 11: 53 mPa ⁇ s ⁇ 1 of Example 20: 87 mPa ⁇ s ⁇ 1 of Example 28: 81 mPa ⁇ s ⁇ 1 of Example 34: 50 mPa ⁇ s ⁇ 1 of Example 44: 47 mPa ⁇ s ⁇ 1 of Example 47: 58 mPa ⁇ s ⁇ 1 of Example 56: 84 mPa ⁇ s (Examples 67 and 68) Using a first substrate in which a pair of transparent electrodes having a comb-shaped electrode structure is provided on the same substrate and a second substrate not having an electrode structure, a vertical alignment film is formed on each substrate, and the first substrate and An IPS empty cell having a gap interval of 4.0 microns was fabricated on the second substrate. The liquid crystal composition shown in Examples 46 and 50 was injected into this empty cell to produce a liquid crystal display device, and the electro-opticalignion
- a liquid crystal cell is applied by a high-pressure mercury lamp through a filter that cuts ultraviolet light of 300 nm or less while applying a rectangular wave of 1.8 V at a frequency of 1 KHz. Were irradiated with ultraviolet rays. The cell surface was adjusted to have an irradiation intensity of 20 mW / cm 2 and irradiated for 600 seconds to obtain a vertically aligned liquid crystal display element in which the polymerizable compound in the polymerizable liquid crystal composition was polymerized. The electro-optical characteristics of these display elements were measured. The results are shown in the table below.
Abstract
Description
A01~A03はそれぞれ独立して下記の何れかの構造を表し、
式中の部分構造式(LC0-Ph)は式(LC0-Np)であることもでき
Y01は-Cl、-F、-OCHF2、-CF3、-OCF3、炭素数2~5のフッ素化されたアルキル基、アルコキシ基、アルケニル基またはアルケニルオキシ基を表し、
Z01~Z05はそれぞれ独立して単結合、-CH=CH-、-C≡C-、-CH2CH2-、-(CH2)4-、-OCH2-、-CH2O-、-OCF2-又は-CF2O-を表し、存在するZ01~Z05の内の少なくとも1つは-OCH2-、-OCF2-又は-CF2O-であり、
W01及びW02はそれぞれ独立して-CH2-又は-O-を表し、
m01~m03はそれぞれ独立して0~2の整数を表し、m01+m02+m03は0、1又は2を表し、A01、A02、A03、Z01、Z03及び/又はZ05が複数存在する場合、それらは同一であっても、異なっていてもよい。)
式中の部分構造式(LC0-Ph)は式(LC0-Np)であることもできる。
Y01は-Cl、-F、-OCHF2、-CF3、-OCF3、炭素数2~5のフッ素化されたアルキル基、アルコキシ基、アルケニル基またはアルケニルオキシ基を表す。)
X01~X05はFであることが大きな誘電率異方性(Δε)又は同程度の誘電率異方性(Δε)に対し顕著に低い粘度(η)となることから好ましい。一般式(LC0)の式中F置換の数は、既に一般式(LC0)に記載されている2個を含め、2~7個が好ましい。
・Z02が-OCH2-、-OCF2-又は-CF2O-である化合物
・Z03が存在し、Z03が-OCH2-、-OCF2-又は-CF2O-である化合物
・Z04が-OCH2-、-OCF2-又は-CF2O-である化合物
・Z05が存在し、Z05が-OCH2-、-OCF2-又は-CF2O-である化合物
・W01及びW02が共に-CH2-である化合物
・W01、W02の1つが-O-である化合物
・W01及びW02が共に-O-である化合物
・m01+m02+m03が0である化合物
・m01が0で、m02が0で、m03が1である化合物
・m01が0で、m02が1で、m03が0である化合物
・m01が1で、m02が0で、m03が0である化合物
・m01が1で、m02が0で、m03が1である化合物
・m01が1で、m02が1で、m03が0である化合物
・m01が0で、m02が1で、m03が1である化合物
・m01が2であって、一方のZ01が-OCH2-、-OCF2-又は-CF2O-で、他方のZ01が単結合である化合物
・m02が1又は2であって、Z02とZ03の内の1つが-OCH2-、-OCF2-又は-CF2O-で、残りのZ02とZ03が単結合である化合物
・m03が1又は2であって、Z04とZ05の内の1つが-OCH2-、-OCF2-又は-CF2O-で、残りのZ04とZ05が単結合である化合物
一般式(LC0)で表される液晶化合物は、下記一般式(LC0-a)から(LC0-d)
(式中、R01、A01からA03、Z01からZ05、X01、X02及びY01は一般式(LC0)における同じ意味を表し、2個以上存在する場合にはそれぞれ同一であっても異なっていてもよい。)で表される化合物であることがより好ましい。本発明の液晶組成物は、一般式(LC0)で表される化合物として、(LC0-a)から(LC0-d)で表される化合物を1種又は2種以上含有することが好ましい。
・一般式(LC0-10)~一般式(LC0-18)で表される化合物であって、多くとも60質量%含有する
・一般式(LC0-28)~一般式(LC0-38)で表される化合物であって、多くとも60質量%含有する
・一般式(LC0-48)~一般式(LC0-51)で表される化合物であって、多くとも30質量%含有する
・一般式(LC0-52)~一般式(LC0-53)で表される化合物であって、多くとも40質量%含有する
・一般式(LC0-56)~一般式(LC0-59)で表される化合物であって、多くとも50質量%含有する
・一般式(LC0-60)~一般式(LC0-67)で表される化合物であって、多くとも20質量%含有する
・一般式(LC0-68)~一般式(LC0-74)で表される化合物であって、多くとも15質量%含有する
・一般式(LC0-2)~一般式(LC0-5)、一般式(LC0-7)、一般式(LC0-11)~一般式(LC0-15)、一般式(LC0-17)、一般式(LC0-18)、一般式(LC0-20)、一般式(LC0-28)~一般式(LC0-30)、一般式(LC0-34)、一般式(LC0-35)、一般式(LC0-39)、一般式(LC0-41)、一般式(LC0-45)、一般式(LC0-46)、一般式(LC0-56)~一般式(LC0-61)、一般式(LC0-68)又は一般式(LC0-74)で表される化合物群から選ばれる1種又は2種以上の化合物を含有する
R01が炭素数1~5のアルキル基又は炭素数2~5のアルケニル基であり、Y01は-Cl、-F、-OCHF2、-CF3、-OCF3、-CF2CF3、-CHFCF3、-OCF2CF3、-OCHFCF3、-OCF=CF2又は-OCH=CF2である一般式(LC0)の化合物が、多くとも70質量%含有することが好ましい。
・一般式(LC2)で表される化合物を多くとも40質量%含有する
・一般式(LC3)で表される化合物を多くとも50質量%含有する
・一般式(LC4)で表される化合物を多くとも60質量%含有する
・一般式(LC5)で表される化合物を多くとも75質量%含有する
これらの一般式(LC1)から一般式(LC5)中、R11~R41はそれぞれ独立して炭素数1~15のアルキル基を表し、該アルキル基中の1つ又は2つ以上の-CH2-は、酸素原子が直接隣接しないように、-O-、-CH=CH-、-CO-、-OCO-、-COO-、-C≡C-、-CF2O-又は-OCF2-で置換されてよく、該アルキル基中の1つ又は2つ以上の水素原子は任意にハロゲンで置換されていてもよいが、炭素数1~8のアルキル基、炭素数2~8のアルケニル基又は炭素数1~8のアルコキシ基であることが好ましく、直鎖であることが好ましく、R51及びR52はそれぞれ独立して炭素数1~15のアルキル基を表し、該アルキル基中の1つ又は2つ以上の-CH2-は、酸素原子が直接隣接しないように、-O-、-CH=CH-、-CO-、-OCO-、-COO-又は-C≡C-で置換されてよいが、炭素数1~8のアルキル基、炭素数2~8のアルケニル基又は炭素数1~8のアルコキシ基であることが好ましく、直鎖であることが好ましい。R11~R52がアルケニル基の場合、式(R1)から式(R5)のいずれかで表される基から選ばれることが好ましい。
A11~A42はそれぞれ独立してトランス-1,4-シクロヘキシレン基、1,4-フェニレン基、3-フルオロ-1,4-フェニレン基、3,5-ジフルオロ-1,4-フェニレン基又はテトラヒドロピラン基が好ましい。A11~A42にテトラヒドロピラン基が含まれる場合には、A11、A21及びA31であることが好ましい。A51~A53はそれぞれ独立してトランス-1,4-シクロヘキシレン基、1,4-フェニレン基、2-フルオロ-1,4-フェニレン基又は3-フルオロ-1,4-フェニレン基が好ましい。
で表される化合物であることが好ましい。
本発明の液晶組成物は、20℃での粘度ηが20mPa・s以下であることが好ましい。
より好ましくは、重合性化合物一般式(PC)におけるMGpが以下の構造
(式中、C01~C03はそれぞれ独立して1,4-フェニレン基、1,4-シクロヘキシレン基、1,4-シクロヘキセニル基、テトラヒドロピラン-2,5-ジイル基、1,3-ジオキサン-2,5-ジイル基、テトラヒドロチオピラン-2,5-ジイル基、1,4-ビシクロ(2,2,2)オクチレン基、デカヒドロナフタレン-2,6-ジイル基、ピリジン-2,5-ジイル基、ピリミジン-2,5-ジイル基、ピラジン-2,5-ジイル基、1,2,3,4-テトラヒドロナフタレン-2,6-ジイル基、2,6-ナフチレン基、フェナントレン-2,7-ジイル基、9,10-ジヒドロフェナントレン-2,7-ジイル基、1,2,3,4,4a,9,10a-オクタヒドロフェナントレン2,7-ジイル基又はフルオレン2,7-ジイル基を表し、1,4-フェニレン基、1,2,3,4-テトラヒドロナフタレン-2,6-ジイル基、2,6-ナフチレン基、フェナントレン-2,7-ジイル基、9,10-ジヒドロフェナントレン-2,7-ジイル基、1,2,3,4,4a,9,10a-オクタヒドロフェナントレン2,7-ジイル基及びフルオレン-2,7-ジイル基は置換基として1個以上のF、Cl、CF3、OCF3、シアノ基、炭素原子数1~8のアルキル基、アルコキシ基、アルカノイル基、アルカノイルオキシ基、炭素原子数2~8のアルケニル基、アルケニルオキシ基、アルケノイル基又はアルケノイルオキシ基を有していても良く、Zp1及びZp2はそれぞれ独立して-COO-、-OCO-、-CH2CH2-、-OCH2-、-CH2O-、-CH=CH-、-C≡C-、-CH=CHCOO-、-OCOCH=CH-、-CH2CH2COO-、-CH2CH2OCO-、-COOCH2CH2-、-OCOCH2CH2-、-CONH-、-NHCO-又は単結合を表し、p3は0、1又は2を表す。)
ここで、Sp1及びSp2はそれぞれ独立してアルキレン基である場合、該アルキレン基は1つ以上のハロゲン原子又はCNにより置換されていても良く、この基中に存在する1つ又は2つ以上のCH2基はO原子が直接隣接しないように-O-、-S-、-NH-、-N(CH3)-、-CO-、-COO-、-OCO-、-OCOO-、-SCO-、-COS-又は-C≡C-により置き換えられていてもよい。また、P1及びP2はそれぞれ独立して下記の一般式
(式中、Rp2からRp6はそれぞれ独立して水素原子、ハロゲン原子又は炭素原子数1~5のアルキル基を表す。)
より具体的には、重合性化合物一般式(PC)が一般式(PC0-1)から一般式(PC0-6)
重合性化合物の使用量は好ましくは0.05~2.0質量%である。
Ze1、Ze2はそれぞれ独立して単結合、-CH=CH-、-C≡C-、-CH2CH2-、-(CH2)4-、-COO-、-OCO-、-OCH2-、-CH2O-、-OCF2-又は-CF2O-を表し
E1はシクロヘキサン環又はベンゼン環を表し、シクロヘキサン環中の1つ又は2つ以上の-CH2-は酸素原子が直接隣接しないように-O-で置換されていてもよく、また該環注の1つ又は2つ以上の-CH2CH2-は-CH=CH-、-CF2O-又は-OCF2-で置換されていてもよく、ベンゼン環中の1つ又は2つ以上の-CH=は窒素原子が直接隣接しないように、-N=で置換されていてもよく、該環中の1つ以上の水素原子がF、Cl、CH3で置換されていてもよく、q1は0、1、2又は3を表す。)
本発明の液晶組成物は、液晶表示素子特にアクティブマトリックス駆動用液晶表示素子として、例えばTNモード、OCBモード、ECBモード、IPS(FFS電極を含む)モード又はVA-IPSモード(FFS電極を含む)に使用することが出来る。ここで、VA-IPSモードとは、電圧無印加時に、誘電率異方性が正の液晶材料(Δε>0)を基板面に対し垂直に配向させ、同一基板面上に配置した画素電極と共通電極により液晶分子を駆動する方法であり、画素電極と共通電極で発生する湾曲電界の方向に液晶分子が配列することから、容易に画素分割やマルチドメインを形成することができ、応答にも優れる利点がある。非特許文献Proc.13th IDW,97(1997)、Proc.13th IDW,175(1997)、SID Sym.Digest,319(1998)、SID Sym.Digest,838(1998)、SID Sym.Digest,1085(1998)、SID Sym.Digest,334(2000)、Eurodisplay Proc.,142(2009)によれば、EOC、VA-IPSなど種々の呼称がされているが、本発明においては以下「VA-IPS」と略称する。
一方、VA-IPS方式においては、本発明等は下記数4が適用されることを見出した。
TN-I :ネマチック相-等方性液体相転移温度(℃)
T-n :ネマチック相の下限温度(℃)
ε⊥ :25℃での分子長軸方向に対し垂直な方向の誘電率
Δε :25℃での誘電率異方性
no :25℃での常光に対する屈折率
Δn :25℃での屈折率異方性
Vth :25℃での周波数1KHzの矩形波を印加した時の透過率が10%変化するセル厚6μmのセルでの印加電圧(V)
η20 :20℃でのバルク粘性(mPa・s)
γ1 :回転粘性(mPa・s)
化合物記載に下記の略号を使用する。
以下に、調製した液晶組成物とその物性値を示す。
(実施例2)
以下に、一般式(LC5)の化合物で構成した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、本発明の液晶組成物における20℃のγ1の物性値を示す。本発明の液晶組成物は、誘電率異方性(Δε)の大きさに対してγ1は比較的小さく、本発明の組み合わせが非常に優れたものであることがわかる。
実施例11のγ1:53mPa・s
実施例20のγ1:87mPa・s
実施例28のγ1:81mPa・s
実施例34のγ1:50mPa・s
実施例44のγ1:47mPa・s
実施例47のγ1:58mPa・s
実施例56のγ1:84mPa・s
(実施例67及び68)
櫛形電極構造の透明電極を同一基板に一対設けた第一の基板と電極構造を設けない第二の基板を使用し各々の基板上に垂直配向性の配向膜を形成し、第一の基板と第二の基板をギャップ間隔4.0ミクロンのIPS用空セルを作製した。この空セルに実施例46及び50で示された液晶組成物を注入し液晶表示素子を作製し、電気光学特性を測定した。
Claims (28)
- 正の誘電率異方性を有する液晶組成物であって、前記液晶組成物が一般式(LC0)で表される化合物を1種又は2種以上含有することを特徴とする液晶組成物。
A01~A03はそれぞれ独立して下記の何れかの構造を表し、
式中の部分構造式(LC0-Ph)は式(LC0-Np)であることもでき
Y01は-Cl、-F、-OCHF2、-CF3、-OCF3、炭素数2~5のフッ素化されたアルキル基、アルコキシ基、アルケニル基またはアルケニルオキシ基を表し、
Z01~Z05はそれぞれ独立して単結合、-CH=CH-、-C≡C-、-CH2CH2-、-(CH2)4-、-OCH2-、-CH2O-、-OCF2-又は-CF2O-を表し、存在するZ01~Z05の内の少なくとも1つは-OCH2-、-OCF2-又は-CF2O-であり、
W01及びW02はそれぞれ独立して-CH2-又は-O-を表し、
m01~m03はそれぞれ独立して0~2の整数を表し、m01+m02+m03は0、1又は2を表し、A01、A02、A03、Z01、Z03及び/又はZ05が複数存在する場合、それらは同一であっても、異なっていてもよい。) - 一般式(LC0)が以下のいずれかの化合物である請求項1記載の液晶組成物。
・Z01が存在し、Z01が-OCH2-、-OCF2-又は-CF2O-である化合物
・Z02が-OCH2-、-OCF2-又は-CF2O-である化合物
・Z03が存在し、Z03が-OCH2-、-OCF2-又は-CF2O-である化合物
・Z04が-OCH2-、-OCF2-又は-CF2O-である化合物
・Z05が存在し、Z05が-OCH2-、-OCF2-又は-CF2O-である化合物
・W01及びW02が共に-CH2-である化合物
・W01、W02の1つが-O-である化合物
・W01及びW02が共に-O-である化合物
・m01+m02+m03が0である化合物
・m01が0で、m02が0で、m03が1である化合物
・m01が0で、m02が1で、m03が0である化合物
・m01が1で、m02が0で、m03が0である化合物
・m01が1で、m02が0で、m03が1である化合物
・m01が1で、m02が1で、m03が0である化合物
・m01が0で、m02が1で、m03が1である化合物
・m01が2であって、一方のZ01が-OCH2-、-OCF2-又は-CF2O-で、他方のZ01が単結合である化合物
・m02が1又は2であって、Z02とZ03の内の1つが-OCH2-、-OCF2-又は-CF2O-で、残りのZ02とZ03が単結合である化合物
・m03が1又は2であって、Z04とZ05の内の1つが-OCH2-、-OCF2-又は-CF2O-で、残りのZ04とZ05が単結合である化合物 - 前記液晶組成物が一般式(LC1)~一般式(LC5)で表される化合物群から選ばれる1種又は2種以上の化合物を含有する請求項1又は2に記載の液晶組成物。
- R01が炭素数1~5のアルキル基又は炭素数2~5のアルケニル基であり、Y01は-Cl、-F、-OCHF2、-CF3、-OCF3、-CF2CF3、-CHFCF3、-OCF2CF3、-OCHFCF3、-OCF=CF2又は-OCH=CF2である一般式(LC0)で表される化合物を1種以上含有し、その含有量の合計が多くとも70質量%である請求項1~3のいずれか一項に記載の液晶組成物。
- 一般式(LC0)で表される化合物を1種以上含有し、下記事項の少なくとも1つを満たす請求項1~4のいずれか一項に記載の液晶組成物。
・一般式(LC1)で表される化合物を多くとも20質量%含有する
・一般式(LC2)で表される化合物を多くとも40質量%含有する
・一般式(LC3)で表される化合物を多くとも50質量%含有する
・一般式(LC4)で表される化合物を多くとも60質量%含有する
・一般式(LC5)で表される化合物を多くとも75質量%含有する - 一般式(LC0)で表される化合物を含有する液晶組成物が下記事項の少なくとも1つを満たす請求項6記載の液晶組成物。
・一般式(LC0-2)~一般式(LC0-9)で表される化合物を多くとも40質量%含有する
・一般式(LC0-10)~一般式(LC0-18)で表される化合物を多くとも60質量%含有する
・一般式(LC0-28)~一般式(LC0-38)で表される化合物を多くとも60質量%含有する
・一般式(LC0-48)~一般式(LC0-51)で表される化合物を多くとも30質量%含有する
・一般式(LC0-52)~一般式(LC0-53)で表される化合物を多くとも40質量%含有する
・一般式(LC0-56)~一般式(LC0-59)で表される化合物を多くとも50質量%含有する
・一般式(LC0-60)~一般式(LC0-67)で表される化合物を多くとも20質量%含有する
・一般式(LC0-68)~一般式(LC0-74)で表される化合物を多くとも15質量%含有する - 一般式(LC0)で表される化合物が、一般式(LC0-2)~一般式(LC0-5)、一般式(LC0-7)、一般式(LC0-11)~一般式(LC0-15)、一般式(LC0-17)、一般式(LC0-18)、一般式(LC0-20)、一般式(LC0-28)~一般式(LC0-30)、一般式(LC0-34)、一般式(LC0-35)、一般式(LC0-39)、一般式(LC0-41)、一般式(LC0-45)、一般式(LC0-46)、一般式(LC0-56)~一般式(LC0-61)、一般式(LC0-68)又は一般式(LC0-74)で表される化合物である請求項6記載の液晶組成物。
- 光学活性化合物を1種又は2種以上含有する請求項1から13のいずれか一項に記載の液晶組成物。
- R11からR41が炭素数2~5のアルケニル基である一般式(LC1)から一般式(LC4)で表される化合物群から選ばれる1種又は2種以上の化合物を含有する請求項3から14のいずれか一項に記載の液晶組成物。
- 一般式(LC1)におけるA11がテトラヒドロピラン-2,5-ジイル基である化合物、一般式(LC2)に存在するA21~A23のうち少なくとも1つがテトラヒドロピラン-2,5-ジイル基である化合物、一般式(LC3)に存在するA31~A32のうち少なくとも1つがテトラヒドロピラン-2,5-ジイル基である化合物、一般式(LC4)に存在するA41~A42のうち少なくとも1つがテトラヒドロピラン-2,5-ジイル基である化合物及び一般式(LC5)に存在するA51~A53のうち少なくとも1つがテトラヒドロピラン-2,5-ジイル基である化合物で表される化合物からなる群から選ばれる1種又は2種以上の化合物を含有する請求項3から15のいずれか一項に記載の液晶組成物。
- 一般式(LC3)に存在するZ31~Z32のうち少なくとも1つが-CF2O-又は-OCH2-である化合物、一般式(LC4)に存在するZ41~Z42のうち少なくとも1つが-CF2O-又は-OCH2-である化合物及び一般式(LC5)に存在するZ51~Z52のうち少なくとも1つが-CF2O-又は-OCH2-である化合物からなる群から選ばれる1種又は2種以上の化合物を含有する請求項3から16のいずれか一項に記載の液晶組成物。
- 一般式(LC5)で表される化合物を30~70質量%含有し、液晶組成物の20℃での粘度ηが20mPa・s以下である請求項3から17のいずれか一項に記載の液晶組成物。
- 重合性化合物を1種又は2種以上含有する請求項1から18のいずれか一項に記載の液晶組成物。
- 酸化防止剤を1種又は2種以上含有する請求項1から19のいずれか一項に記載の液晶組成物。
- UV吸収剤を1種又は2種以上含有する請求項1から20のいずれか一項に記載の液晶組成物。
- 請求項1から21のいずれか一項に記載の液晶組成物を用いた液晶表示素子。
- 請求項1から21のいずれか一項に記載の液晶組成物を用いたアクティブマトリックス駆動用液晶表示素子。
- 請求項1から21のいずれか一項に記載の液晶組成物を用いたTNモード、OCBモード、ECBモード、IPSモード又はVA-IPSモード用液晶表示素子。
- 請求項19に記載の液晶組成物を用い、電圧印加下あるいは電圧無印加下で該液晶組成物中に含有する重合性化合物を重合させて作製した高分子安定化のTNモード、OCBモード、ECBモード、IPSモード又はVA-IPSモード用液晶表示素子。
- 液晶分子と接する面で該液晶分子を水平、チルト及び又は垂直に配向させる配向層が、ポリイミド(PI)、ポリアミド、カルコン、シンナメート又はシンナモイルの少なくとも一種から選ばれた化合物を含有する配向膜である請求項22から25のいずれか一項に記載の液晶表示素子。
- 請求項26記載の配向層に更に重合性液晶化合物及び又は重合性非液晶化合物を含有する液晶表示素子。
- 液晶組成物と接する面の配向層として、光配向技術を用いて作製した配向膜を設けた請求項23及び又は27記載の液晶表示素子。
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WO2016199668A1 (ja) * | 2015-06-12 | 2016-12-15 | Dic株式会社 | 組成物及びそれを使用した液晶表示素子 |
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JPWO2016199668A1 (ja) * | 2015-06-12 | 2017-06-22 | Dic株式会社 | 組成物及びそれを使用した液晶表示素子 |
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WO2018207635A1 (ja) * | 2017-05-09 | 2018-11-15 | Dic株式会社 | 組成物及びそれを使用した液晶表示素子 |
JP2019167547A (ja) * | 2019-05-27 | 2019-10-03 | Jnc株式会社 | ハロゲン化されたアルキルを有する液晶化合物、液晶組成物および液晶表示素子 |
Also Published As
Publication number | Publication date |
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JPWO2015029876A1 (ja) | 2017-03-02 |
US20160186059A1 (en) | 2016-06-30 |
US10544365B2 (en) | 2020-01-28 |
TW201527491A (zh) | 2015-07-16 |
JP5776864B1 (ja) | 2015-09-09 |
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