WO2014030482A1 - 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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- WO2014030482A1 WO2014030482A1 PCT/JP2013/070058 JP2013070058W WO2014030482A1 WO 2014030482 A1 WO2014030482 A1 WO 2014030482A1 JP 2013070058 W JP2013070058 W JP 2013070058W WO 2014030482 A1 WO2014030482 A1 WO 2014030482A1
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- liquid crystal
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- 0 Cc1cc(F)c(C)c(*C=C)c1 Chemical compound Cc1cc(F)c(C)c(*C=C)c1 0.000 description 6
- QRMPKOFEUHIBNM-UHFFFAOYSA-N CC1CCC(C)CC1 Chemical compound CC1CCC(C)CC1 QRMPKOFEUHIBNM-UHFFFAOYSA-N 0.000 description 1
- YEJCHVFCLNKZPU-UHFFFAOYSA-N CC1COC(C)CC1 Chemical compound CC1COC(C)CC1 YEJCHVFCLNKZPU-UHFFFAOYSA-N 0.000 description 1
- RPMUDXVQHUECRE-UHFFFAOYSA-N CC1COC(C)OC1 Chemical compound CC1COC(C)OC1 RPMUDXVQHUECRE-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
- URLKBWYHVLBVBO-UHFFFAOYSA-N Cc1ccc(C)cc1 Chemical compound Cc1ccc(C)cc1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 1
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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
- C09K19/3066—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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- C09K19/08—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
- C09K19/20—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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- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
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- 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-)
- C09K2019/122—Ph-Ph
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- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/12—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-)
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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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- C09K19/06—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
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3004—Cy-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
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/301—Cy-Cy-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)
- C09K2019/3012—Cy-Cy-Cy-Ph, or more Cy rings
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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
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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
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- C09K2019/3025—Cy-Ph-Ph-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
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- C09K2019/548—Macromolecular compounds stabilizing the alignment; Polymer stabilized alignment
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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
- G02F1/0009—Materials therefor
- 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
- 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 object is provided.
- the liquid crystal composition contains one or more compounds selected from compounds represented by the general formula (LC0)
- 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 object is provided.
- R 01 represents an alkenyl group having 2 to 5 carbon atoms
- R 11 to R 41 each independently represents an alkyl group having 1 to 15 carbon atoms, and one or two or more of the alkyl groups
- —CH 2 — in which —O—, —CH ⁇ CH—, —CO—, —OCO—, —COO—, —C ⁇ C—, —CF 2 O— -OCF 2- may be substituted
- one or more hydrogen atoms in the alkyl group may be optionally substituted with halogen
- R 51 and R 52 each independently represents 1 to 15 represents an alkyl group, and one or more —CH 2 — in the alkyl group is —O—, —CH ⁇ CH—, —CO—, —OCO, so that the oxygen atom is not directly adjacent.
- a 51 or A 53 described later In the case of a chlorohexane ring, it may be —OCF 3 or —CF 3 —, and A 01 to A 42 are each independently 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
- X 61 and X 62 are each independently —H, —Cl, —F, —CF 3 or — OCF 3 is represented
- 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 the general formula (LC0) and the compounds represented by the general formula (LC1) to the general formula (LC5) exhibits a stable liquid crystal phase even at a low temperature. It can be said that.
- R 01 in the general formula (LC0) is an alkenyl group having 2 to 5 carbon atoms, and is preferably selected from groups represented by any one of the formulas (R1) to (R5).
- R 01 in the general formula (LC0) is an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms.
- 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. Or a tetrahydropyran-2,5-diyl group is preferred.
- a 01 to A 42 contain a tetrahydropyran-2,5-diyl group, A 01 , A 11 , A 21 , A 31 and A 41 are preferable.
- 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 in the general formula (LC0) is F because the viscosity ( ⁇ ) is remarkably low with respect to 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.
- 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 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).
- a compound group in which X 33 and X 34 in the general formula (LC3-20) and the general formula (LC3-21) are F and / or the general formula (LC3-25), the general formula (LC3-26), the general formula ( A compound selected from the group of compounds having a tetrahydropyran ring represented by general formula (LC3-32) from LC3-30) is also more preferable.
- 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 further more preferable that it is a compound represented by these.
- To the compound group represented by formula (LC4-17) is more preferably used in combination with formula (LC0) which is an essential component of the present invention.
- R 51 and R 52 represent the same meaning as in general formula (LC5)), and are more preferable.
- 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)
- the compound group represented by general formula (LC0) which is an essential component of the present invention is used in combination.
- at least one of R 51 and R 52 is more preferably an alkenyl group, and any one of the alkenyl groups of the following formulas (R1) to (R5) More preferably it is.
- One or more compounds represented by the general formula (LC5) are preferably contained, and the content is preferably 30 to 70% by mass, and more preferably 20% to 70% by mass.
- the liquid crystal composition of the present invention contains a compound represented by general formula (LC0) and a compound selected from the group of compounds represented by general formula (LC1) to general formula (LC5).
- the content of the represented compound is preferably in the range of 5 to 50% by mass, and more preferably in the range of 10 to 40% 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 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 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 supporting group
- R p1 represents a halogen atom, a cyano group or an alkyl group having 1 to 25 carbon atoms, and one or two or more CH 2 groups in the alkyl group are —O -, -S-, -NH-, -N (CH 3 )-, -CO
- 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 p 3 represents 0, 1 or 2.
- 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—, —OC
- 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
- R p1 is F, CF 3 , OCF 3 , CH 3 or OCH 3
- the number of substitutions of the substituent R p1 is 1, 2, 3 or 4 A polymerizable compound.
- 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).
- the amount of the polymerizable compound used is preferably 0.05 to 2.0% by mass.
- the liquid crystal composition of the present invention containing a polymerizable compound is produced by polymerizing the polymerizable compound. At this time, it is desired to reduce the unpolymerized component to less than desired.
- the liquid crystal composition of the present invention suitable for this preferably contains a compound having a biphenyl group and / or a terphenyl group as a partial structure in the general formula (LC0). 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 It is preferable to select one or two or more compounds from the group of compounds represented by -107) to contain 0.1 to 40% by mass. In addition, it is preferably used in combination with a polymerizable compound represented by general formula (PL1-1) to general formula (PL1-3), general formula (PC1-8) or general formula (PC1-9).
- 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).
- 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.
- 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 3).
- 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.
- the liquid crystal compositions of Examples 2-10 has a low viscosity, gamma 1 is small, it can be seen that the combination of the present invention is that excellent.
- Example 11 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 Example 1 was injected into this empty cell to produce a liquid crystal display element.
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Abstract
Description
一般式(LC0)におけるR01が炭素数1~8のアルキル基、又は炭素数1~8のアルコキシ基である化合物を併用することも好ましい。
m01~m51はそれぞれ独立して0~3の整数を表すことが出来るが、m01+m02は1又は2が特に好ましく、m21は0が特に好ましく、m31+m32は1、2又は3が特に好ましく、m41+m42は1又は2が特に好ましい。
(式中、R01、A01、A02、A03、Z01、Z02、X01及びY01は一般式(LC0)におけると同じ意味を表し、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さらに好ましい。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は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。更にこの中で、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1種又は2種以上含有することは特に好ましい。
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、該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)
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、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)
粘度: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。
(実施例3)
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11)
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1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1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-A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。この表示素子は、実施例1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、非常に速い応答速度であった。
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)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。
- 一般式(LC1)から一般式(LC5)に存在するR02からR41、R51及び又はR52が炭素数2~5のアルケニル基である化合物を1種又は2種以上含有する請求項1から7のいずれか一項に記載の液晶組成物。
- 一般式(LC0)から一般式(LC5)に存在するA11からA42及び又はA51からA53の少なくともいずれかひとつがテトラヒドロピラン-2,5-ジイル基である化合物を1種又は2種以上含有する請求項1から8のいずれか一項に記載の液晶組成物。
- 一般式(LC0)、一般式(LC3)から一般式(LC5)に存在するZ01、Z02、Z31からZ42、Z51及び又はZ52の少なくともいずれかひとつが-C2FO-又は-OCF2-である化合物を1種又は2種以上含有する請求項1から9のいずれか一項に記載の液晶組成物。
- 一般式(LC5)で表される化合物を30~70質量%含有し、20℃でのバルク粘度ηが20mPa・s以下である請求項1から10のいずれか一項に記載の液晶組成物。
- 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を設けた請求項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ことを特徴とした液晶表示素子。
- 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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WO2014030482A1 (ja) | 2012-08-22 | 2014-02-27 | Dic株式会社 | ネマチック液晶組成物 |
KR101555596B1 (ko) | 2012-08-22 | 2015-09-24 | 디아이씨 가부시끼가이샤 | 네마틱 액정 조성물 |
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KR20140145205A (ko) | 2014-12-22 |
JP5534382B1 (ja) | 2014-06-25 |
DE112013004127B4 (de) | 2016-08-11 |
KR101555597B1 (ko) | 2015-09-24 |
JPWO2014030482A1 (ja) | 2016-07-28 |
TWI588244B (zh) | 2017-06-21 |
US9587175B2 (en) | 2017-03-07 |
DE112013004127T5 (de) | 2015-05-07 |
CN104471030B (zh) | 2016-04-27 |
CN104471030A (zh) | 2015-03-25 |
TW201422789A (zh) | 2014-06-16 |
US20150203757A1 (en) | 2015-07-23 |
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