WO2013018796A1 - ネマチック液晶組成物 - Google Patents
ネマチック液晶組成物 Download PDFInfo
- Publication number
- WO2013018796A1 WO2013018796A1 PCT/JP2012/069461 JP2012069461W WO2013018796A1 WO 2013018796 A1 WO2013018796 A1 WO 2013018796A1 JP 2012069461 W JP2012069461 W JP 2012069461W WO 2013018796 A1 WO2013018796 A1 WO 2013018796A1
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- WIPO (PCT)
- Prior art keywords
- liquid crystal
- crystal composition
- general formula
- group
- ocf
- Prior art date
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- HBXFIXSFKULBOG-UHFFFAOYSA-N Cc1cc(F)c(C)c(F)c1 Chemical compound Cc1cc(F)c(C)c(F)c1 HBXFIXSFKULBOG-UHFFFAOYSA-N 0.000 description 2
- QRMPKOFEUHIBNM-UHFFFAOYSA-N CC1CCC(C)CC1 Chemical compound CC1CCC(C)CC1 QRMPKOFEUHIBNM-UHFFFAOYSA-N 0.000 description 1
- MHWDRWADMYCKKC-UHFFFAOYSA-N Cc(cc1)ccc1-c(ccc(C)c1)c1F Chemical compound Cc(cc1)ccc1-c(ccc(C)c1)c1F MHWDRWADMYCKKC-UHFFFAOYSA-N 0.000 description 1
- WJAVYWPXOXAOBS-UHFFFAOYSA-N Cc1cc(F)c(C)cc1 Chemical compound Cc1cc(F)c(C)cc1 WJAVYWPXOXAOBS-UHFFFAOYSA-N 0.000 description 1
- 0 N#CC=CC(CC1)CCC1c1ccc(*c2cc(F)c(C(F)(F)F)c(F)c2)cc1 Chemical compound N#CC=CC(CC1)CCC1c1ccc(*c2cc(F)c(C(F)(F)F)c(F)c2)cc1 0.000 description 1
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- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
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- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
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- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
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- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
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- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
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- C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
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- C09K19/16—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon double bonds, e.g. stilbenes
- C09K2019/161—Ph-CH=CH-Ph
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- C09K2019/181—Ph-C≡C-Ph
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- C09K2019/183—Ph-Ph-C≡C-Ph
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- C09K2019/3036—Cy-C2H4-Ph
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3028—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon single bonds
- C09K2019/304—Cy-C2H4-Ph-Ph
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3048—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon double bonds
- C09K2019/305—Cy-CH=CH-Cy
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3048—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon double bonds
- C09K2019/3051—Cy-CH=CH-Cy-Ph
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3059—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon triple bonds
- C09K2019/3063—Cy-Ph-C≡C-Ph
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
- C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
- C09K2019/3077—Cy-Cy-COO-Ph
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- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
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- 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
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, and VA type and horizontal alignment that feature vertical alignment using TFT (thin film transistor).
- 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
- the problem to be solved by the present invention is adjusted to a desired refractive index anisotropy ( ⁇ n) to suppress a decrease in the nematic phase-isotropic liquid phase transition temperature (T ni ) and an increase in the minimum temperature of the nematic phase.
- ⁇ n refractive index anisotropy
- 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 selected from compounds represented by the general formula (LC0), Furthermore, the present invention provides a liquid crystal composition comprising one or more compounds selected from the group of compounds represented by general formula (LC1) to general formula (LC5), and further provides the liquid crystal composition A liquid crystal display element using the above is provided.
- R 01 to R 41 each independently represents 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. 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 51 or A 53 described later is a cyclohexane ring, —OCF 3 or —CF 3-
- a 01 to A 42 are each independently one of the following structures:
- One or more —CH 2 — of 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
- the above —CH ⁇ may be substituted with —N ⁇ so that the nitrogen atom is not directly adjacent to each other, and X 61 and X 62 are each independently —H, —Cl, —F, —CF 3 or — OCF 3 is represented), and
- a 51 to A 53 are each independently any one of the following structures:
- X 01 represents a hydrogen atom or a fluorine atom
- X 11 to X 43 each independently represents —H, —Cl, —F, —CF 3 or —OCF 3
- Y 01 to Y 41 each represent —Cl, —F, —OCHF 2 , —CF 3 or —OCF 3 .
- each of m 01 to m 51 independently represents an integer of 0 to 3
- m 01 + m 02 , m 31 + m 32 and m 41 + m 42 are each independently 1, 2, 3 or 4 and A 01 , A 03 , A 23 , A 31 , A 32 , A 41 , A 42 , A 52 , Z 01 , Z 02 , Z 31 , Z 32 , Z 41 , If Z 42 and / or Z 52 there are a plurality, they may be the same , It may be different. )
- 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. Further, it is a practical and reliable liquid crystal composition that is chemically stable to heat, light, water, and the like and can be driven at a low voltage.
- the liquid crystal composition in the present invention contains one or more compounds selected from the compounds represented by the general formula (LC0), and further compounds represented by the general formulas (LC1) to (LC5). 1 type, or 2 or more types of compounds chosen from the compound group which consists of these are contained.
- a liquid crystal composition containing the compound represented by general formula (LC0) and the compounds represented by general formula (LC1) to general formula (LC5) exhibits a stable liquid crystal phase even at a low temperature. It can be said that.
- R 01 to R 52 are each independently 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. It is preferably a group and is preferably a straight chain.
- R 01 to R 52 are alkenyl groups, they are preferably selected from groups represented by any one of formulas (R1) to (R5).
- a 01 , A 11 , A 21 , A 31 , A 41 , A 51 , A 53 is a trans-1,4-cyclohexylene group, these are preferable, and these are preferably represented by formula (R1), formula (R2), formula (R4 Is more preferable. It is more preferable that at least one of R 51 and R 53 in the general formula (LC5) contains one or more compounds each of which is an alkenyl group of any one of the formulas (R1) to (R5).
- a 01 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.
- Groups and tetrahydropyran groups are preferred.
- a 01 to A 42 include a tetrahydropyran group, A 01 , A 11 , A 21 and A 31 are preferable.
- Specific preferred compounds having a tetrahydropyran group include general formulas (LC0-7) to general formulas (LC0-9), general formulas (LC0-23), general formulas (LC0-24), and general formulas (described later).
- LC0-26 general formula (LC0-27), general formula (LC0-20), general formula (LC0-40), general formula (LC0-51) to general formula (LC0-53), general formula (LC0- 110), general formula (LC0-111), general formula (LC2-9) to general formula (LC2-14), general formula (LC3-23) to general formula (LC3-32), general formula (LC4-12) To general formula (LC4-14), general formula (LC4-16), general formula (LC4-19) and general formula (LC4-22). 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.
- a 51 to A 53 are each independently a trans-1,4-cyclohexylene group, 1,4-phenylene group, 3-fluoro-1,4-phenylene group or 2-fluoro-1,4-phenylene group. preferable.
- Z 31 to Z 42 are each independently a single bond, —CH ⁇ CH—, —C ⁇ C—, —CH 2 CH 2 —, —OCH 2 —, —CH 2 O—, —OCF 2 — or —CF 2 O— is preferred, and one of Z 31 to Z 42 present is —CH ⁇ CH—, —C ⁇ C—, —CH 2 CH 2 —, — (CH 2 ) 4 —, —OCF 2 — or —CF When it represents 2 O—, the others are preferably single bonds.
- the others are preferably single bonds, more preferably all represent single bonds.
- X 01 is particularly preferably F because it has a significantly low viscosity ( ⁇ ) for a large dielectric anisotropy ( ⁇ ) or a comparable dielectric anisotropy ( ⁇ ).
- X 11 to X 43 are each independently preferably H or F, and X 11 , X 21 , X 31 , and X 41 are preferably F.
- Y 01 to Y 41 are each independently preferably F, CF 3 or OCF 3 .
- m 01 to m 51 can each independently represent an integer of 0 to 3, but m 01 + m 02 is more preferably 1 or 2, m 21 is more preferably 0, and m 31 + m 32 is 1, 2. Or 3 is more preferable, and m 41 + m 42 is more preferably 1 or 2.
- the liquid crystal compounds represented by the general formula (LC0) are represented by the following general formulas (LC0-a) to (LC0-h). Wherein R 01 , A 01 , A 02 , A 03 , Z 01 , Z 02 , X 01 and Y 01 represent the same meaning in the general formula (LC0), and A 01 , A 03 and / or Z 01 , When two or more Z02 are present, they may be the same or different from each other.
- the liquid crystal composition of the present invention preferably contains one or more compounds represented by (LC0-a) to (LC0-h) as the compound represented by the general formula (LC0).
- R represents the same meaning as R 01 in formula (LC0)
- —F, CF 3 , OCF 3 each independently represents either —F, CF 3 or OCF 3 ;
- -F is more preferably a compound represented by H or F as a substituent.
- the compounds represented by the general formulas (LC0-1) to (LC0-19) 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 (LC0-20) to (LC0-111) 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 ).
- X 23 , X 24 , X 25 and X 26 each independently represent a hydrogen atom, Cl, F, CF 3 or OCF 3 , and X 22 , R 21 and Y 21 in the general formula (LC2) It is more preferable that it is a compound represented by the same meaning.
- the compound groups represented by general formula (LC2-1) to general formula (LC2-4) and general formula (LC2-9) to general formula (LC2-11) are more preferable.
- the compounds represented by general formula (LC3) are represented by the following general formula (LC3-1) to general formula (LC3-32).
- X 33 , X 34 , X 35 , X 36 , X 37 and X 38 each independently represent H, Cl, F, CF 3 or OCF 3
- X 32 , R 31 , A 31 , Y 31 and Z 31 are more preferably compounds represented by general formula (LC3).
- the compounds represented by the general formula (LC3-5), the general formula (LC3-15), and the general formula (LC3-20) to the general formula (LC3-32) are the general formulas that are essential components of the present invention. More preferably, it is used in combination with (LC0).
- X 44 , X 45 , X 46 and X 47 each independently represent H, Cl, F, CF 3 or OCF 3
- X 42 , X 43 , R 41 and Y 41 represent the general formula (LC4 ) Represents the same meaning as in It is preferable that it is a compound represented by these.
- general formula (LC4-1) to general formula (LC4-3), general formula (LC4-6), general formula (LC4-9), general formula (LC4-10), general formula (LC4-12) Therefore, it is more preferable to use the compound group represented by the general formula (LC4-17) together with the general formula (LC0) which is an essential component of the present invention.
- a compound selected from the group of compounds wherein X 44 and / or X 45 in formula (LC4-9) to formula (LC4-11) and formula (LC4-15) to formula (LC4-17) is F is It is more preferable to use together with the general formula (LC0) which is an essential component of the invention.
- R 51 and R 52 represent the same meanings in general formula (LC5)), and are preferably compounds represented by Of these, from general formula (LC5-1) to general formula (LC5-8), general formula (LC5-14), general formula (LC5-16), and general formula (LC5-18) to general formula (LC5-26) It is more preferable to use together the compound group represented by general formula (LC0) which is an essential component of this invention.
- a compound group in which at least one of R 51 and R 52 in formulas (LC5-1) and (LC5-4) is an alkenyl group, particularly any one of the following alkenyl groups of formulas (R1) to (R5) More preferably.
- One or more compounds represented by the general formula (LC5) are contained, and the content is preferably 20 to 70% by mass, and more preferably 30 to 70% by mass.
- 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 twist effect. As such an optically active compound, specifically, liquid crystals such as cholesteric nonanate and compounds represented by the following general formulas (Ch-1) to (Ch-6) are preferable.
- 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 chain group or halogen substituent having optical activity, and 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 -CF 2 O-a represents, D 1
- D 2 is Cyclohexane represents a ring or a benzene ring
- one or two or more -CH 2 in the cyclohexane ring - may have an oxygen atom which may be substituted with -O- so as not to directly adjacent
- Two or more —CH 2 CH 2 — may be substituted with —CH ⁇ CH—, —CF 2 O— or —OCF 2 —
- one or more —CH 2 in the benzene ring ⁇ may be substituted with —N ⁇ such that the nitrogen atom is not directly adjacent
- 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 nucleus of the molecule.
- 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 polymerizable compound having a biphenyl group and / or a terphenyl group in the partial structure in the general formula (LC0). It is preferable to do. More specifically, the general formula (LC0-4) to the general formula (LC0-6), the general formula (LC0-10) to the general formula (LC0-16), and the general formula (LC0-27) to the general formula (LC0). The compound represented by -107) 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 of Fredericks transition in TN and ECB systems
- the VA system is represented by the formula (III).
- 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 formula (IV) 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 (Expression of anisotropy) From the formula (IV), the cell configuration is as small as possible for d gap and as large as possible for d ITO, and the absolute value of ⁇ of the liquid crystal composition to be used is increased. , K33 can be selected to reduce the drive voltage.
- the liquid crystal composition of the present invention can be adjusted to preferable ⁇ , K11, and K33.
- 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 preferably 0.31 to 0.33 in the TN mode, ECB mode, and IPS mode. In the VA-IPS mode, 0.20 to 0.59 is preferable in the case of vertical alignment with respect to both substrates, and 0.30 to 0.40 is particularly preferable.
- the suitability value of the product ( ⁇ n ⁇ d) varies depending on the mode type of each display element, so that the refractive index anisotropy ( ⁇ n) of the liquid crystal composition is in a range of 0.070 to 0.110, and There is a need for a liquid crystal composition having a refractive index anisotropy ( ⁇ n) in the range of 100 to 0.140, or in a range different from the range of 0.130 to 0.180.
- the general formula (LC0-1) to the general formula (LC0-3) in order to obtain a small or relatively small refractive index anisotropy ( ⁇ n), the general formula (LC0-1) to the general formula (LC0-3), the general formula (LC0-7) To general formula (LC0-9), from general formula (LC0-20) to general formula (LC0-30) selected from the group consisting of compounds represented by general formula (LC0-30), containing 0.1 to 80% by mass
- the general formula (LC0-4) to the general formula (LC0-6) and the general formula (LC0-10) to the general formula ( LC0-16 one selected from the group consisting of compounds represented by general formula (LC0-27) to general formula (LC0-107), or two or more, and is preferably contained in an amount of 0.1 to 60% by mass.
- the tilt angle in the TN mode and ECB mode where the liquid crystal alignment when no voltage is applied needs to be substantially horizontal is preferably 0.5 to 7 °, and the liquid crystal alignment when no voltage is applied needs to be approximately perpendicular to the substrate surface.
- the tilt angle is preferably 85 to 90 °.
- an alignment film made of polyimide (PI), polyamide, chalcone, cinnamate, cinnamoyl, or the like can be provided. Further, it is preferable to use an alignment film prepared by using a photo-alignment technique.
- the liquid crystal composition of the present invention containing the compound in which X 01 in the general formula (LC0) is F can be easily aligned on the easy axis of the alignment film and can easily control a desired tilt angle.
- liquid crystal composition of the present invention containing the compound represented by the general formula (PC) as the polymerizable compound is obtained by polymerizing the polymerizable compound contained in the liquid crystal composition with voltage applied or without voltage applied.
- the produced polymer stabilized liquid crystal display element for TN mode, OCB mode, ECB mode, IPS mode or VA-IPS mode can be provided.
- 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 where 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 The prepared liquid crystal composition and its physical property values are shown below.
- Example 2 The prepared liquid crystal composition and its physical property values are shown below.
- Example 3 The prepared liquid crystal composition and its physical property values are shown below.
- the liquid crystal composition is a liquid crystal composition in which the compound represented by the general formula (LC0) of Example 3 is replaced with a compound having —CF 2 O— as a linking group. It can be seen that Example 3 has a much lower viscosity, ⁇ 1 is smaller, Tni is higher, and the combination of the present invention is very excellent. (Comparative Example 2) The prepared liquid crystal composition and its physical property values are shown below.
- the liquid crystal composition is a liquid crystal composition in which the compound represented by the general formula (LC0) in Example 3 is replaced with a compound having —CH 2 O— as a linking group. It can be seen that Example 3 has a much lower viscosity, ⁇ 1 is smaller, Tni is higher, and the combination of the present invention is very excellent. (Comparative Example 3) The prepared liquid crystal composition and its physical property values are shown below.
- the liquid crystal composition is a liquid crystal composition not containing the compound represented by the general formula (LC0) of the present application. It can be seen that Example 3 has a much lower viscosity, ⁇ 1 is smaller, and the combination of the present invention is very excellent. (Example 4) The prepared liquid crystal composition and its physical property values are shown below.
- the liquid crystal composition is a liquid crystal composition not containing the compound represented by the general formula (LC0) of the present application.
- Example 4 has a much lower viscosity and a smaller ⁇ 1 , indicating that the combination of the present invention is very good.
- 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.
- liquid crystal composition contains the compounds represented by the general formula (LC0), general formula (LC2), and general formula (LC5) of the present application, low viscosity and small ⁇ 1 can be realized even in a low ⁇ n system. It can be seen that the combination of the present invention is very excellent. (Example 8) The prepared liquid crystal composition and its physical property values are shown below.
- Example 9 A liquid crystal base composition A composed of the compounds represented by general formula (LC5-1), general formula (LC5-4) and general formula (LC5-7) was prepared as follows.
- liquid crystal composition prepared using the liquid crystal base composition A and its physical properties are shown.
- the liquid crystal composition is a liquid crystal composition not containing the compound represented by the general formula (LC0) of the present application.
- Example 9 has a much lower viscosity, ⁇ 1 is also smaller, and it can be seen that the combination of the present invention is very excellent (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.
- the liquid crystal compositions of Examples 1 to 18 are low viscosity, gamma 1 is small, it can be seen that the combination of the present invention is that excellent.
- Example 19 Using a first substrate having a pair of transparent electrodes having a comb-shaped electrode structure 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.
- a liquid crystal display element was produced by injecting the liquid crystal composition shown in Example 12 into this empty cell. When the electro-optical characteristics of this display element were measured, the applied voltage at which the transmittance changed by 10% was 1.45v. The response speed when 5v was applied was 4.6 milliseconds, and the response speed when the voltage was turned off was 11.9 seconds.
- a polymerizable liquid crystal composition CLC-A was prepared by adding 1% and uniformly dissolving.
- the physical properties of CLC-A were almost the same as those of the liquid crystal composition shown in Example 12.
- UV light is irradiated to the liquid crystal cell by a high-pressure mercury lamp through a filter that cuts UV light of 300 nm or less while applying a rectangular wave of 1.8 V at a frequency of 1 KHz. did.
- 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 applied voltage at which the transmittance changed by 10% was 1.58 v.
- the response speed when 5v was applied was 4.2 milliseconds.
- the response speed when the voltage was turned off was 4.7 milliseconds, which was very fast compared to the liquid crystal display device manufactured using only the liquid crystal composition shown in Example 12.
- Example 20 The prepared liquid crystal composition and its physical property values are shown below.
- the liquid crystal composition is a liquid crystal composition not including the compound represented by the general formula (LC0) of Example 20.
- a much lower viscosity is more embodiments 20, gamma 1 is small, Tni is high, it can be seen that the combination of the present invention is that excellent.
- Example 21 The prepared liquid crystal composition and its physical property values are shown below.
- the liquid crystal composition is a liquid crystal composition not containing the compound represented by the general formula (LC0) of the present application.
- Example 21 has a much lower viscosity and smaller ⁇ 1 , indicating that the combination of the present invention is very excellent (Comparative Example 8).
- the prepared liquid crystal composition and its physical property values are shown below.
- the liquid crystal composition is a liquid crystal composition not containing the compound represented by the general formula (LC0) of the present application. It can be seen that Example 21 is driven at a lower voltage and has a lower viscosity, ⁇ 1 is also smaller, and the combination of the present invention is very excellent. (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.
- the liquid crystal compositions of Examples 3-9 are low viscosity, gamma 1 is small, it can be seen that the combination of the present invention is that excellent.
- Example 29 Using a first substrate having a pair of transparent electrodes having a comb-shaped electrode structure 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.
- a liquid crystal display device was produced by injecting the liquid crystal composition shown in Example 22 into this empty cell. When the electro-optical characteristics of this display element were measured, the applied voltage at which the transmittance changed by 10% was 1.45v. The response speed when 5v was applied was 4.7 milliseconds, and the response speed when the voltage was turned off was 16.2 seconds.
- a polymerizable liquid crystal composition CLC-B was prepared by adding 1% and uniformly dissolving.
- the physical properties of CLC-B were almost the same as those of the liquid crystal composition shown in Example 22.
- UV light is irradiated to the liquid crystal cell by a high-pressure mercury lamp through a filter that cuts UV light of 300 nm or less while applying a rectangular wave of 1.8 V at a frequency of 1 KHz. did.
- 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 applied voltage at which the transmittance changed by 10% was 1.71v.
- the response speed when 5v was applied was 4.6 milliseconds.
- Example 30 The prepared liquid crystal composition and its physical property values are shown below.
- the liquid crystal composition is a liquid crystal composition not containing the compound represented by the general formula (LC0) of the present application. It can be seen that Example 30 has a much lower viscosity, ⁇ 1 is smaller, and the combination of the present invention is very excellent (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.
- the liquid crystal compositions of Examples 31-38 are low viscosity, gamma 1 is small, it can be seen that the combination of the present invention is that excellent.
- Example 39 Using a first substrate having a pair of transparent electrodes having a comb-shaped electrode structure 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.
- a liquid crystal display element was produced by injecting the liquid crystal composition shown in Example 32 into this empty cell. When the electro-optical characteristics of this display element were measured, the applied voltage at which the transmittance changed by 10% was 1.63 v. The response speed when 5v was applied was 4.4 milliseconds, and the response speed when the voltage was turned off was 12.3 seconds.
- a polymerizable liquid crystal composition CLC-C was prepared by adding 1% and uniformly dissolving.
- the physical properties of CLC-C were almost the same as those of the liquid crystal composition shown in Example 32.
- the liquid crystal cell is irradiated with ultraviolet light 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. did.
- 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.
- Example 40 A liquid crystal composition containing a compound represented by the general formula (LC0) and a liquid crystal composition not containing the compound are prepared, and their physical property values are shown below.
- the liquid crystal composition of Example 1 contains a compound represented by the general formula (LC0-98) of the present invention, and the liquid crystal composition of Comparative Example 10 contains a compound represented by the general formula (LC0).
- the liquid crystal composition does not. ⁇ and ⁇ n show substantially the same value, but in Example 1, the Tni greatly increased, the upper limit temperature of the liquid crystal phase was greatly expanded, and the viscosity was reduced by about 20%. It can be seen that the combination of the invention is very good. (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.
- the liquid crystal compositions of Examples 2-8 are low viscosity, gamma 1 is small, it can be seen that the combination of the present invention is that excellent.
- Example 48 Using a first substrate having a pair of transparent electrodes having a comb-shaped electrode structure 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. A liquid crystal display device was produced by injecting the liquid crystal composition shown in Example 44 into this empty cell. When the electro-optical characteristics of this display element were measured, the applied voltage at which the transmittance changed by 10% was 1.33 v. The response speed when 5v was applied was 4.4 milliseconds, and the response speed when the voltage was turned off was 11.9 seconds.
- a polymerizable liquid crystal composition CLC-D was prepared by adding 1% and uniformly dissolving.
- the physical properties of CLC-D were almost the same as those of the liquid crystal composition shown in Example 44.
- UV light is irradiated to the liquid crystal cell with a high-pressure mercury lamp through a filter that cuts UV light of 300 nm or less while applying a 1.8 V rectangular wave at a frequency of 1 KHz. did.
- 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 applied voltage at which the transmittance changed by 10% was 1.36 v.
- the response speed when 5v was applied was 4.5 milliseconds.
- Example 49 The prepared liquid crystal composition and its physical property values are shown below.
- the liquid crystal composition is a liquid crystal composition containing no compound represented by the general formula (LC0) having a partial structure of -Ph3-OCH 2 -of the present application.
- Example 1 has a much lower viscosity and a smaller ⁇ 1 despite a large dielectric anisotropy ( ⁇ ) and a high nematic phase-isotropic liquid phase transition temperature (T ni ). It can be seen that the combination of the invention is very excellent (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 Using a first substrate having a pair of transparent electrodes having a comb-shaped electrode structure 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. A liquid crystal display device was produced by injecting the liquid crystal composition shown in Example 49 into this empty cell.
- a polymerizable liquid crystal composition CLC-E was prepared by adding 1% and uniformly dissolving.
- the physical properties of CLC-E were almost the same as those of the liquid crystal composition shown in Example 49.
- UV light is irradiated to the liquid crystal cell by a high-pressure mercury lamp through a filter that cuts UV light of 300 nm or less while applying a 1.8 V rectangular wave at a frequency of 1 KHz. did.
- 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.
- This display element had a very fast response speed as compared with the liquid crystal display element produced only with the liquid crystal composition shown in Example 49.
- Example 60 The prepared liquid crystal composition and its physical property values are shown below.
- the liquid crystal composition is a liquid crystal composition containing no compound represented by the general formula (LC0) having a partial structure of -Ph3-OCH 2 -of the present application.
- Example 1 has a much lower viscosity and a smaller ⁇ 1 despite a large dielectric anisotropy ( ⁇ ) and a high nematic phase-isotropic liquid phase transition temperature (T ni ). It can be seen that the combination of the invention is very good.
- 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 Using a first substrate having a pair of transparent electrodes having a comb-shaped electrode structure 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.
- a liquid crystal display device was produced by injecting the liquid crystal composition shown in Example 60 into this empty cell.
- a polymerizable liquid crystal composition CLC-F was prepared by adding 1% and uniformly dissolving.
- the physical properties of CLC-F were almost the same as those of the liquid crystal composition shown in Example 60.
- UV light is irradiated to the liquid crystal cell with a high-pressure mercury lamp through a filter that cuts UV light of 300 nm or less while applying a rectangular wave of 1.8 V at a frequency of 1 KHz. did.
- 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.
- This display element had a very fast response speed as compared with the liquid crystal display element produced only with the liquid crystal composition shown in Example 60.
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Abstract
Description
A01、A11、A21、A31、A41、A51、A53がトランス-1,4-シクロヘキシレン基の場合、これらは好ましく、式(R1)、式(R2)、式(R4)が更に好ましい。一般式(LC5)におけるR51、R53の少なくとも一方が式(R1)から式(R5)のいずれかのアルケニル基である化合物を1種又は2種以上含有することは更に好ましい。
(式中、R01、A01、A02、A03、Z01、Z02、X01及びY01は一般式(LC0)における同じ意味を表し、A01、A03及び/又はZ01、Z02が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。
で表される化合物であることが好ましい。この内、一般式(LC4-1)から一般式(LC4-3)、一般式(LC4-6)、一般式(LC4-9)、一般式(LC4-10)、一般式(LC4-12)から一般式(LC4-17)で表される化合物群を本発明の必須成分である一般式(LC0)と併用することがより好ましい。一般式(LC4-9)から一般式(LC4-11)及び一般式(LC4-15)から一般式(LC4-17)におけるX44及び又はX45がFである化合物群から選ばれる化合物を本発明の必須成分である一般式(LC0)と併用することが更に好ましい。
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、本発明者等によって、式(IV)が適用されることを見出している。
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。
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。
(比較例2)
以下に、調製した液晶組成物とその物性値を示す。
(比較例3)
以下に、調製した液晶組成物とその物性値を示す。
(実施例4)
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。
(実施例5)
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。
(実施例8)
以下に、調製した液晶組成物とその物性値を示す。
(実施例9)
以下のような、一般式(LC5-1)、一般式(LC5-4)及び一般式(LC5-7)で表される化合物で構成される液晶ベース組成物Aを調製した。
以下に、液晶組成物Aを用いて調製した液晶組成物とその物性値を示す。
(実施例10)
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。
(実施例19)
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12で示された液晶組成物を注入し液晶表示素子を作製した。この表示素子の電気光学特性を測定したところ、透過率が10%変化する印加電圧は、1.45vであった。また、5vを印加した時の応答速度は4.6ミリ秒であり、電圧をオフにした時の応答速度は11.9秒であった。
(実施例20)
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。
(実施例21)
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。
(比較例8)
以下に、調製した液晶組成物とその物性値を示す。
(実施例22)
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。
(実施例29)
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22で示された液晶組成物を注入し液晶表示素子を作製した。この表示素子の電気光学特性を測定したところ、透過率が10%変化する印加電圧は、1.45vであった。また、5vを印加した時の応答速度は4.7ミリ秒であり、電圧をオフにした時の応答速度は16.2秒であった。
この実施例22で示された液晶組成物99%に対して、式(PC-1)-3-1で表される重合性化合物
(実施例30)
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。
(実施例31)
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。
(実施例39)
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32で示された液晶組成物を注入し液晶表示素子を作製した。この表示素子の電気光学特性を測定したところ、透過率が10%変化する印加電圧は、1.63vであった。また、5vを印加した時の応答速度は4.4ミリ秒であり、電圧をオフにした時の応答速度は12.3秒であった。
この実施例32で示された液晶組成物99%に対して、式(PC-1)-3-1で表される重合性化合物
上述のIPS用空セルにCLC-Cを挟持した後、周波数1KHzで1.8Vの矩形波を印加しながら、300nm以下の紫外線をカットするフィルターを介して、高圧水銀灯により液晶セルに紫外線を照射した。セル表面の照射強度が20mW/cm2となるように調整して600秒間照射して、重合性液晶組成物中の重合性化合物を重合させた垂直配向性液晶表示素子を得た。この表示素子の電気光学特性を測定したところ、透過率が10%変化する印加電圧は、1.86vであった。また、5vを印加した時の応答速度は4.4ミリ秒であった。また、電圧をオフにした時の応答速度は4.3ミリ秒と、実施例32で示された液晶組成物のみで作製した液晶表示素子と比較して、非常に速いものであった。
(実施例40及び比較例10)
一般式(LC0)で表される化合物を含有する液晶組成物及び含有しない液晶組成物を調製し、以下にその物性値を示す。
(実施例41)
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。
(実施例48)
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44で示された液晶組成物を注入し液晶表示素子を作製した。この表示素子の電気光学特性を測定したところ、透過率が10%変化する印加電圧は、1.33vであった。また、5vを印加した時の応答速度は4.4ミリ秒であり、電圧をオフにした時の応答速度は11.9秒であった。
(実施例49)
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。
(実施例50)
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。
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49で示された液晶組成物を注入し液晶表示素子を作製した。
(実施例60)
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。
(実施例61)
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。
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60で示された液晶組成物を注入し液晶表示素子を作製した。
この実施例60で示された液晶組成物99%に対して、式(PC-1)-3-1で表される重合性化合物
Claims (22)
- 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)で表される化合物から選ばれる1種又は2種以上の化合物を含有し、さらに一般式(LC1)から一般式(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ことを特徴とする液晶組成物。
- 一般式(LC0)で表される化合物から選ばれる1種又は2種以上の化合物を含有し、さらに一般式(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し、さらに一般式(LC5)で表される化合物群より選ばれる1種又は2種以上の化合物を含有する請求項1記載の液晶組成物。
- 一般式(LC0)においてX01がFである請求項1又は2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7のいずれか一項に記載の液晶組成物。
- R01からR52が炭素数2~5のアルケニル基である一般式(LC0)から一般式(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から8のいずれか一項に記載の液晶組成物。
- 一般式(LC0)に存在するA01~A03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(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1から9のいずれか一項に記載の液晶組成物。
- 一般式(LC0)に存在するZ01~Z02のうち少なくとも1つが-CF2O-又は-OCF2-である化合物、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-OCF2-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-OCF2-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-OCF2-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1から10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1から11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12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13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14のいずれか一項に記載の液晶組成物。
- 請求項1から15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16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17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13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16から19のいずれか一項に記載の液晶表示素子。
- 請求項20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20及び又は21記載の液晶表示素子。
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KR101488314B1 (ko) | 2015-01-30 |
JP5376269B2 (ja) | 2013-12-25 |
US9039929B2 (en) | 2015-05-26 |
TWI565789B (zh) | 2017-01-11 |
CN103717708A (zh) | 2014-04-09 |
CN104861988B (zh) | 2017-05-24 |
JPWO2013018796A1 (ja) | 2015-03-05 |
US20140225036A1 (en) | 2014-08-14 |
CN103717708B (zh) | 2017-03-22 |
CN104861988A (zh) | 2015-08-26 |
KR20140031383A (ko) | 2014-03-12 |
TW201313882A (zh) | 2013-04-01 |
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