JP5780431B2 - Nematic liquid crystal composition - Google Patents
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- JP5780431B2 JP5780431B2 JP2012036203A JP2012036203A JP5780431B2 JP 5780431 B2 JP5780431 B2 JP 5780431B2 JP 2012036203 A JP2012036203 A JP 2012036203A JP 2012036203 A JP2012036203 A JP 2012036203A JP 5780431 B2 JP5780431 B2 JP 5780431B2
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- 239000000203 mixture Substances 0.000 title claims description 66
- 239000004988 Nematic liquid crystal Substances 0.000 title description 2
- 239000004973 liquid crystal related substance Substances 0.000 claims description 91
- 150000001875 compounds Chemical class 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000006096 absorbing agent Substances 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000011159 matrix material Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- -1 3,5-difluoro-1,4-phenylene Chemical group 0.000 description 14
- 230000000704 physical effect Effects 0.000 description 13
- 210000004027 cell Anatomy 0.000 description 8
- 239000000758 substrate Substances 0.000 description 7
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 101100328110 Arabidopsis thaliana CLC-A gene Proteins 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- 125000004959 2,6-naphthylene group Chemical group [H]C1=C([H])C2=C([H])C([*:1])=C([H])C([H])=C2C([H])=C1[*:2] 0.000 description 2
- 125000005451 3-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:1])C([H])=C(F)C([*:2])=C1[H] 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000005407 trans-1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])[C@]([H])([*:2])C([H])([H])C([H])([H])[C@@]1([H])[*:1] 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- 125000005714 2,5- (1,3-dioxanylene) group Chemical group [H]C1([H])OC([H])([*:1])OC([H])([H])C1([H])[*:2] 0.000 description 1
- 239000004985 Discotic Liquid Crystal Substance Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 150000008423 fluorobenzenes Chemical class 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Liquid Crystal Substances (AREA)
Description
本発明は電気光学的液晶表示材料として有用な誘電率異方性（Δε）が正の値を示すネマチック液晶組成物に関する。 The present invention relates to a nematic liquid crystal composition having a positive dielectric anisotropy (Δε) useful as an electro-optical liquid crystal display material.
液晶表示素子は、時計、電卓をはじめとして、各種測定機器、自動車用パネル、ワードプロセッサー、電子手帳、プリンター、コンピューター、テレビ、時計、広告表示板等に用いられるようになっている。液晶表示方式としては、その代表的なものにＴＮ（ツイステッド・ネマチック）型、ＳＴＮ（スーパー・ツイステッド・ネマチック）型、ＴＦＴ（薄膜トランジスタ）を用いた垂直配向型やＩＰＳ（イン・プレーン・スイッチング）型等がある。これらの液晶表示素子に用いられる液晶組成物は水分、空気、熱、光などの外的要因に対して安定であること、また、室温を中心としてできるだけ広い温度範囲で液晶相を示し、低粘性であり、かつ駆動電圧が低いことが求められる。さらに液晶組成物は個々の表示素子に対してあわせ最適な誘電率異方性（Δε）または及び屈折率異方性（Δｎ）等を最適な値とするために、数種類から数十種類の化合物から構成されている。 Liquid crystal display elements are used in various measuring instruments, automobile panels, word processors, electronic notebooks, printers, computers, televisions, watches, advertisement display boards, as well as watches and calculators. Typical liquid crystal display methods include TN (twisted nematic) type, STN (super twisted nematic) type, vertical alignment type using TFT (thin film transistor), and IPS (in-plane switching) type. Etc. 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. Furthermore, the liquid crystal composition has several to several tens of kinds of compounds in order to optimize the dielectric anisotropy (Δε) and the refractive index anisotropy (Δn) for each display element. It is composed of
垂直配向型ディスプレイではΔεが負の液晶組成物が用いられており、ＴＮ型、ＳＴＮ型又はＩＰＳ型等の水平配向型ディスプレイではΔεが正の液晶組成物が用いられている。また、Δεが正の液晶組成物を電圧無印加時に垂直に配向させ、横電界を印加する事で表示する駆動方式も報告されており、Δεが正の液晶組成物の必要性はさらに高まっている。一方、全ての駆動方式において低電圧駆動、高速応答、広い動作温度範囲が求められている。すなわち、Δεが正で絶対値が大きく、粘度（η）が小さく、高いネマチック相−等方性液体相転移温度（Ｔｎｉ）が要求されている。また、Δｎとセルギャップ（ｄ）との積であるΔｎ×ｄの設定から、液晶組成物のΔｎをセルギャップに合わせて適当な範囲に調節する必要がある。加えて液晶表示素子をテレビ等へ応用する場合においては高速応答性が重視されるため、γ１の小さい液晶組成物が要求される。 A liquid crystal composition having a negative Δε is used for a vertical alignment type display, and a liquid crystal composition having a positive Δε is used for a horizontal alignment type display such as a TN type, STN type, or IPS type. In addition, a driving method has been reported in which a liquid crystal composition having a positive Δε is vertically aligned when no voltage is applied and a horizontal electric field is applied to display the liquid crystal composition, and the necessity of a liquid crystal composition having a positive Δε is further increased. Yes. On the other hand, low voltage driving, high-speed response, and a wide operating temperature range are required in all driving systems. That is, Δε is positive, the absolute value is large, the viscosity (η) is small, and a high nematic phase-isotropic liquid phase transition temperature (T ni ) is required. Further, from the setting of Δn × d, which is the product of Δn and the cell gap (d), it is necessary to adjust Δn of the liquid crystal composition to an appropriate range according to the cell gap. In addition, when applying a liquid crystal display element to a television or the like, since high-speed response is important, a liquid crystal composition having a small γ 1 is required.
液晶組成物の構成成分として、Δεが正の液晶化合物である式（Ａ−１）や（Ａ−２）で表される化合物を使用した液晶組成物の開示があるが（特許文献１から４）、これら液晶組成物は十分に低い粘性を実現するに至っていない。 There is a disclosure of a liquid crystal composition using a compound represented by the formula (A-1) or (A-2) which is a liquid crystal compound having a positive Δε as a constituent component of the liquid crystal composition (Patent Documents 1 to 4). These liquid crystal compositions have not yet achieved a sufficiently low viscosity.
本発明が解決しようとする課題は、屈折率異方性（Δｎ）およびネマチック相−等方性液体相転移温度（Ｔｎｉ）を低減又は上昇させることなく、粘度（η）が十分に低く、なおかつ、誘電率異方性（Δε）が正の液晶組成物を提供することにある。 The problem to be solved by the present invention is that the viscosity (η) is sufficiently low without reducing or increasing the refractive index anisotropy (Δn) and the nematic phase-isotropic liquid phase transition temperature (T ni ), In addition, another object is to provide a liquid crystal composition having a positive dielectric anisotropy (Δε).
本発明者は、種々のフルオロベンゼン誘導体を検討し、特定の化合物を組み合わせることにより前記課題を解決することができることを見出し、本件発明を完成するに至った。 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.
本発明は、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（ＬＣ１）及び／又は一般式（ＬＣ２）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（ＬＣ３）から一般式（ＬＣ７）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を提供し、更に、当該液晶組成物を用いた液晶表示素子を提供する。 The present invention is a liquid crystal composition having a positive dielectric anisotropy, wherein the liquid crystal composition is one or two selected from compounds represented by the general formula (LC1) and / or the general formula (LC2) Provided is a liquid crystal composition comprising one or more compounds selected from the group of compounds represented by general formula (LC3) to general formula (LC7), which contains one or more compounds. Furthermore, a liquid crystal display element using the liquid crystal composition is provided.
（式中、Ｒ１１及びＲ２１は炭素数１〜１５のアルキル基を表し、該アルキル基中の１つ又は２つ以上のＣＨ２基は、酸素原子が直接隣接しないように、−Ｏ−、−ＣＨ＝ＣＨ−、−ＣＯ−、−ＯＣＯ−、−ＣＯＯ−、−Ｃ≡Ｃ−、−ＣＦ２Ｏ−、−ＯＣＦ２−で置換されてよく、該アルキル基中の１つ又は２つ以上の水素原子は任意にハロゲン置換されていてもよく、Ａ１１及びＡ２１はそれぞれ独立して下記の何れかの構造 (In the formula, R 11 and R 21 represent an alkyl group having 1 to 15 carbon atoms, and one or two or more CH 2 groups in the alkyl group are —O— so that the oxygen atom is not directly adjacent to each other. , -CH = CH -, - CO -, - OCO -, - COO -, - C≡C -, - CF 2 O -, - OCF 2 - may be replaced by one in the alkyl group or Two or more hydrogen atoms may be optionally halogen-substituted, and A 11 and A 21 are each independently any one of the following structures:
（該構造中、Ｘ１及びＸ２はそれぞれ独立して−Ｈ、−Ｃｌ、−Ｆ、−ＣＦ３又は−ＯＣＦ３を表し、ベンゼン環の１つ又は２つ以上のＣＨ基は窒素原子で置換されていてもよく、また、該構造中の１つ又は２つ以上の水素原子は−Ｃｌ、−ＣＦ３又は−ＯＣＦ３で置換されていてもよい。）を表し、Ａ１２、Ａ１３、Ａ２２、及びＡ２３はそれぞれ独立して下記の何れかの構造 (In the structure, X 1 and X 2 each independently represent —H, —Cl, —F, —CF 3 or —OCF 3, and one or more CH groups in the benzene ring are nitrogen atoms. And one or more hydrogen atoms in the structure may be substituted with —Cl, —CF 3 or —OCF 3 ), and A 12 , A 13 , A 22 and A 23 are each independently one of the following structures:
（該構造中、Ｘ３及びＸ４はそれぞれ独立してＨ、Ｃｌ、Ｆ、ＣＦ３又はＯＣＦ３を表し、シクロヘキサン環の１つ又は２つ以上のＣＨ２基は酸素原子で置換されていてもよく、該構造中ベンゼン環の１つ又は２つ以上のＣＨ基は窒素原子で置換されていてもよく、また、該構造中の１つ又は２つ以上の水素原子はＣｌ、ＣＦ３又はＯＣＦ３で置換されていてもよい。）を表し、Ｙ１１及びＹ２１はそれぞれ独立して−Ｃｌ、−Ｆ、−ＣＦ３又は−ＯＣＦ３を表し、Ｚ１１〜Ｚ２２はそれぞれ独立して単結合、−ＣＨ＝ＣＨ−、−Ｃ≡Ｃ−、−ＣＨ２ＣＨ２−、−（ＣＨ２）４−、−ＯＣＦ２−又は−ＣＦ２Ｏ−を表し、ｍ１１〜ｍ２２はそれぞれ独立して０〜２の整数を表し、ｍ１１＋ｍ１２、及びｍ２１＋ｍ２２はそれぞれ独立して０、１、２又は３を表し、Ａ１１、Ａ１３、Ａ２１、Ａ２３、Ｚ１１、Ｚ１２、Ｚ２１及び／又はＺ２２が複数存在する場合、それらは同一であっても、異なっていてもよい。） (In the structure, X 3 and X 4 each independently represent H, Cl, F, CF 3 or OCF 3, and one or more CH 2 groups of the cyclohexane ring are substituted with oxygen atoms. In the structure, one or more CH groups of the benzene ring may be substituted with a nitrogen atom, and one or more hydrogen atoms in the structure may be Cl, CF 3 or may be substituted with OCF 3.) represents, Y 11 and Y 21 each independently represent -Cl, -F, a -CF 3 or -OCF 3, Z 11 ~Z 22 are each independently A single bond, —CH═CH—, —C≡C—, —CH 2 CH 2 —, — (CH 2 ) 4 —, —OCF 2 — or —CF 2 O—, each of m 11 to m 22 represents independently represents an integer of 0~2, m 11 + m 12, and m 21 + m 2 Independently represent 0, 1, 2 or 3, if A 11, A 13, A 21 , A 23, Z 11, Z 12, Z 21 and / or Z 22 there are a plurality, they are identical in It may or may not be. )
（式中、Ｒ３１〜Ｒ７２はそれぞれ独立して、炭素数１〜１０のアルキル基を表し、該アルキル基中の１つ又は２つ以上のＣＨ２基は、酸素原子が直接隣接しないように、−Ｏ−、−ＣＨ＝ＣＨ−、−ＣＯ−、−ＯＣＯ−、−ＣＯＯ−、−Ｃ≡Ｃ−、−ＣＦ２Ｏ−又は−ＯＣＦ２−で置換されていてもよく、該アルキル基中の１つ又は２つ以上の水素原子は任意にハロゲン置換されていてもよく、Ｘ５及びＸ６はそれぞれ独立してＨ、Ｃｌ、Ｆ、ＣＦ３又はＯＣＦ３を表す。） (Wherein R 31 to R 72 each independently represents an alkyl group having 1 to 10 carbon atoms, and one or more CH 2 groups in the alkyl group are not directly adjacent to each other with an oxygen atom. a, -O -, - CH = CH -, - CO -, - OCO -, - COO -, - C≡C -, - CF 2 O- or -OCF 2 - may be substituted with said alkyl One or more hydrogen atoms in the group may be optionally halogen-substituted, and X 5 and X 6 each independently represent H, Cl, F, CF 3 or OCF 3 )
本発明の液晶組成物は、Δεが正であってその絶対値が大きいという特徴を有する。またηも低く、回転粘性（γ１）も小さく、液晶性に優れ、広い温度範囲で安定な液晶相を示す。更に、熱、光、水等に対し、化学的に安定であり、低電圧駆動が可能である実用的で信頼性の高い液晶組成物である。 The liquid crystal composition of the present invention is characterized in that Δε is positive and its absolute value is large. Also, η is low, rotational viscosity (γ 1 ) is small, liquid crystal properties are 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.
本願発明における液晶組成物は前記一般式（ＬＣ１）及び／又は一般式（ＬＣ２）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（ＬＣ３）から（ＬＣ７）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。一般式（ＬＣ１）及び／又は一般式（ＬＣ２）で表される化合物と一般式（ＬＣ３）から一般式（ＬＣ３）で表される化合物を含む液晶組成物は低温においても安定した液晶相を示すため、実用的な液晶組成物であるということができる。 The liquid crystal composition in the present invention contains one or more compounds selected from the compounds represented by the general formula (LC1) and / or the general formula (LC2), and further from the general formulas (LC3) to (LC7). 1 type or 2 types or more compounds chosen from the compound group represented by this. A liquid crystal composition containing a compound represented by general formula (LC1) and / or general formula (LC2) and a compound represented by general formula (LC3) to general formula (LC3) exhibits a stable liquid crystal phase even at a low temperature. Therefore, it can be said that it is a practical liquid crystal composition.
これらの一般式（ＬＣ１）から一般式（ＬＣ７）中、Ｒ１１〜Ｒ７２はそれぞれ独立して炭素数１〜１５のアルキル基を表し、該アルキル基中の１つ又は２つ以上のＣＨ２基は、酸素原子が直接隣接しないように、−Ｏ−、−ＣＨ＝ＣＨ−、−ＣＯ−、−ＯＣＯ−、−ＣＯＯ−、−Ｃ≡Ｃ−、−ＣＦ２Ｏ−、−ＯＣＦ２−で置換されてよく、該アルキル基中の１つ又は２つ以上の水素原子は任意にハロゲン置換されていてもよいが、炭素数１〜８のアルキル基、炭素数２〜８のアルケニル基又は炭素数１〜８のアルコキシ基であることが好ましく、直鎖であることが好ましい。
Ａ１１及びＡ２１はそれぞれ独立してはトランス−１，４−シクロヘキシレン基、１，４−フェニレン基、３−フルオロ−１，４−フェニレン基又は３，５−ジフルオロ−１，４−フェニレン基が好ましい。
Ａ１２、Ａ１３、Ａ２２及びＡ２３はそれぞれ独立してトランス−１，４−シクロヘキシレン基、１，４−フェニレン基、３−フルオロ−１，４−フェニレン基又は３，５−ジフルオロ−１，４−フェニレン基が好ましい。
Ｘ１、Ｘ２、Ｘ３、Ｘ４、Ｘ５及びＸ６はそれぞれ独立してＨ又はＦが好ましい。
In general formula (LC1) to general formula (LC7), R 11 to R 72 each independently represents an alkyl group having 1 to 15 carbon atoms, and one or two or more CH 2 in the alkyl group. The groups are selected from —O—, —CH═CH—, —CO—, —OCO—, —COO—, —C≡C—, —CF 2 O—, —OCF 2 — so that the oxygen atom is not directly adjacent. 1 or 2 or more hydrogen atoms in the alkyl group may be optionally halogen-substituted, but 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 is preferable, and a straight chain is preferable.
A 11 and A 21 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 are preferred.
A 12 , A 13 , A 22 and A 23 are each independently a trans-1,4-cyclohexylene group, 1,4-phenylene group, 3-fluoro-1,4-phenylene group or 3,5-difluoro- A 1,4-phenylene group is preferred.
X 1 , X 2 , X 3 , X 4 , X 5 and X 6 are each independently preferably H or F.
Ｙ１１及びＹ２１はそれぞれ独立してＦ、ＣＦ３又はＯＣＦ３が好ましく、Ｆ又はＯＣＦ３がより好ましい。
Ｚ１１〜Ｚ２２はそれぞれ独立して単結合、−Ｃ≡Ｃ−、−ＣＨ２ＣＨ２−、−（ＣＨ２）４−、−ＯＣＦ２−又は−ＣＦ２Ｏ−が好ましく、存在するＺ１１及びＺ１２のうち一つが−ＣＨ＝ＣＨ−、−Ｃ≡Ｃ−、−ＣＨ２ＣＨ２−、−（ＣＨ２）４−、−ＯＣＦ２−又は−ＣＦ２Ｏ−を表す場合、他は単結合を表すことが好ましく、全てが単結合を表すことが更に好ましい。
ｍ１１〜ｍ２２はそれぞれ独立して０〜２の整数を表すことが好ましく、ｍ１１＋ｍ１２及びｍ２１＋ｍ２２はそれぞれ独立して１、２又は３が好ましい。
Y 11 and Y 21 are each independently preferably F, CF 3 or OCF 3 , and more preferably F or OCF 3 .
Z 11 to Z 22 are each independently preferably a single bond, —C≡C—, —CH 2 CH 2 —, — (CH 2 ) 4 —, —OCF 2 — or —CF 2 O—. When one of 11 and Z 12 represents —CH═CH—, —C≡C—, —CH 2 CH 2 —, — (CH 2 ) 4 —, —OCF 2 — or —CF 2 O— Preferably represents a single bond, more preferably all represent a single bond.
m 11 to m 22 each independently preferably represents an integer of 0 to 2, and m 11 + m 12 and m 21 + m 22 are each preferably preferably 1, 2 or 3.
一般式（ＬＣ１）で表される液晶化合物は、下記一般式（ＬＣ１−１）〜（ＬＣ１−３） The liquid crystal compounds represented by the general formula (LC1) are represented by the following general formulas (LC1-1) to (LC1-3).
（式中、Ｒ１１、Ａ１１、Ａ１２、Ａ１３、Ｚ１１、Ｚ１２及びＹ１１は一般式（ＬＣ１）におけると同じ意味を表す。）で表される化合物であることがより好ましい。下記一般式（ＬＣ１−１−１）から一般式（ＬＣ１−３−１６） (Wherein R 11 , A 11 , A 12 , A 13 , Z 11 , Z 12 and Y 11 represent the same meaning as in the general formula (LC1)), and more preferably a compound represented by From the following general formula (LC1-1-1) to general formula (LC1-3-16)
（式中、Ｒ１１は一般式（ＬＣ１）におけると同じ意味を表す。）で表される化合物であることがさらに好ましい。 (Wherein R 11 represents the same meaning as in formula (LC1)), and is more preferable.
一般式（ＬＣ２）で表される化合物は、下記一般式（ＬＣ２−１）から一般式（ＬＣ２−３） The compound represented by the general formula (LC2) is represented by the following general formula (LC2-1) to general formula (LC2-3).
（式中、Ｒ２１、Ａ２１、Ａ２２、Ａ２３、Ｚ２１、Ｚ２２及びＹ２１は一般式（ＬＣ１）におけると同じ意味を表す。）で表される化合物であることがより好ましい。下記一般式（ＬＣ２−１−１）から一般式（ＬＣ２−３−１６） (Wherein R 21 , A 21 , A 22 , A 23 , Z 21 , Z 22 and Y 21 represent the same meaning as in the general formula (LC1)), and more preferably a compound represented by From the following general formula (LC2-1-1) to general formula (LC2-3-16)
（式中、Ｒ２１は一般式（ＬＣ２）におけると同じ意味を表す。）で表される化合物であることがさらに好ましい。
本発明の液晶組成物には、高分子安定化（ＰＳ）モードなどの液晶表示素子を作製するために、重合性化合物を含有することができる。使用できる重合性化合物として、光などのエネルギー線により重合が進行する光重合性モノマーなどが挙げられ、構造として、例えば、ビフェニル誘導体、ターフェニル誘導体などの六員環が複数連結した液晶骨格を有する重合性化合物などが挙げられる。具体的には重合性化合物が一般式（ＰＣ１）
(Wherein R 21 represents the same meaning as in formula (LC2)), and is more preferable.
The liquid crystal composition of the present invention can contain a polymerizable compound in order to produce a liquid crystal display device such as a polymer stabilization (PS) mode. Examples of the polymerizable compound that can be used include a photopolymerizable monomer that undergoes polymerization by energy rays such as light. The structure has, for example, a liquid crystal skeleton in which a plurality of six-membered rings such as biphenyl derivatives and terphenyl derivatives are connected. Examples thereof include a polymerizable compound. Specifically, the polymerizable compound is represented by the general formula (PC1).
（式中、Ｐ１は重合性官能基を表し、Ｓｐ１は炭素原子数０〜２０のスペーサー基を表し、Ｑ１は単結合、−Ｏ−、−ＮＨ−、−ＮＨＣＯＯ−、−ＯＣＯＮＨ−、−ＣＨ＝ＣＨ−、−ＣＯ−、−ＣＯＯ−、−ＯＣＯ−、−ＯＣＯＯ−、−ＯＯＣＯ−、−ＣＨ＝ＣＨ−、−ＣＨ＝ＣＨ−ＣＯＯ−、−ＯＣＯ−ＣＨ＝ＣＨ−又は−Ｃ≡Ｃ−を表し、ｎ１及びｎ２はそれぞれ独立して１、２又は３を表し、ＭＧはメソゲン基又はメソゲン性支持基を表し、Ｒ３は、ハロゲン原子、シアノ基又は炭素原子数１〜２５のアルキル基を表し、該アルキル基中の１つ又は２つ以上のＣＨ２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−より置き換えられていても良く、あるいはＲ３はＰ２−Ｓｐ２−Ｑ２−（式中、Ｐ２、Ｓｐ２、Ｑ２はそれぞれ独立してＰ１、Ｓｐ１、Ｑ１と同じ意味を表す。）を表す。）で表される重合性化合物であることが好ましい。 (Wherein P 1 represents a polymerizable functional group, Sp 1 represents a spacer group having 0 to 20 carbon atoms, and Q 1 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—, n 1 and n 2 each independently represent 1, 2 or 3, MG represents a mesogenic group or mesogenic support group, and R 3 represents a halogen atom, a cyano group or the number of carbon atoms 1 to 25 alkyl groups, and one or more CH 2 groups in the alkyl group are —O—, —S—, —NH—, —N (, so that the O atom is not directly adjacent. CH 3) -, - CO - , - COO -, - OCO -, - OCOO -, - SCO -, - CO - or -C≡C- may have more replaced, or R 3 is P 2 -Sp 2 -Q 2 - ( P 1 and wherein, P 2, Sp 2, Q 2 are each independently, Sp 1 , Which represents the same meaning as Q 1 ), and a polymerizable compound represented by
より好ましくは、重合性化合物一般式（ＰＣ１）におけるＭＧが以下の構造 More preferably, MG in the polymerizable compound general formula (PC1) has the following structure:
（式中、Ｃ１〜Ｃ３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、Ｙ１及びＹ２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、ｎ５は０、１又は２を表す。）で表される重合性化合物であり、
Ｓｐ１及びＳｐ２がそれぞれ独立してアルキレン基を表し、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く、
Ｐ１及びＰ２がそれぞれ独立して以下の一般式（ＰＣ１−ａ）〜一般式（ＰＣ１−ｄ）
(Wherein C 1 to C 3 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-diyl group, 1,2,3,4,4a, 9,10a-octahydrophenanthrene 2,7-diyl group or fluorene 2,7 -Diyl group, the 1,4-phenylene group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 2,6-naphthylene group, phenanthrene-2,7-diyl group, 9, 10-dihydrophenanthrene-2,7-diyl group 1,2,3,4,4a, 9,10a- octahydrophenanthrene 2,7-diyl group and fluorene 2,7-diyl group is 1 or more F as substituents, Cl, CF 3, OCF 3 , cyano Group, an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkanoyl group, an alkanoyloxy group, an alkenyl group having 2 to 8 carbon atoms, an alkenyloxy group, an alkenoyl group or an alkenoyloxy group. , Y 1 and Y 2 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 single It represents a bond, n 5 is A polymerizable compound represented by representative.) 1 or 2,
Sp 1 and Sp 2 each independently represent an alkylene group, which may be substituted by one or more halogen atoms or CN, and one or more CH 2 present in this group. The groups are —O—, —S—, —NH—, —N (CH 3 ) —, —CO—, —COO—, —OCO—, —OCOO—, —SCO—, so that the O atom is not directly adjacent. -COS- or -C≡C- may be substituted,
P 1 and P 2 are each independently the following general formula (PC1-a) to general formula (PC1-d)
（式中、Ｒ８１〜Ｒ９２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。）のいずれかで表される。 (Wherein R 81 to R 92 each independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 5 carbon atoms).
より具体的には、重合性化合物一般式（ＰＣ１）が一般式（ＰＣ１）−１又は一般式（ＰＣ１）−２ More specifically, the polymerizable compound general formula (PC1) is represented by the general formula (PC1) -1 or the general formula (PC1) -2.
（式中、Ｐ１、Ｓｐ１、Ｑ１、Ｐ２、Ｓｐ２、Ｑ２及びＭＧは一般式（ＰＣ１）と同じ意味を表し、ｎ３及びｎ４はそれぞれ独立して１、２又は３を表す。）で表される重合性化合物であることが好ましい。 (In the formula, P 1 , Sp 1 , Q 1 , P 2 , Sp 2 , Q 2 and MG represent the same meaning as in the general formula (PC1), and n 3 and n 4 are independently 1, 2 or 3 respectively. It is preferable that it is a polymeric compound represented by this.
より具体的には、一般式（ＰＣ１）が一般式（ＰＣ１）−３〜一般式（ＰＣ１）−８ More specifically, the general formula (PC1) is represented by the general formula (PC1) -3 to the general formula (PC1) -8.
（式中、Ｗ１はそれぞれ独立してＦ、ＣＦ３、ＯＣＦ３、ＣＨ３、ＯＣＨ３、炭素原子数２〜５のアルキル基、アルコキシ基、アルケニル基、ＣＯＯＷ２、ＯＣＯＷ２又はＯＣＯＯＷ２を表し（式中、Ｗ２は炭素原子数１〜１０の直鎖又は分岐鎖アルキル基又は炭素原子数２〜５のアルケニル基を表し、ｎ３、ｎ４及びｎ６はそれぞれ独立して０、１、２、３又は４を表す。）で表される重合性化合物であることがより好ましい。 Wherein W 1 is independently F, CF 3 , OCF 3 , CH 3 , OCH 3 , an alkyl group having 2 to 5 carbon atoms, an alkoxy group, an alkenyl group, COOW 2 , OCOW 2 or OCOW 2 . (Wherein W 2 represents a linear or branched alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and n 3 , n 4 and n 6 are each independently 0, It is more preferably a polymerizable compound represented by 1, 2, 3, or 4.
さらには、一般式（ＰＣ１）−３〜一般式（ＰＣ１）−８におけるＳｐ１、Ｓｐ２、Ｑ１及びＱ２がすべて単結合であり、ｎ３及びｎ４において、ｎ３＋ｎ４が３〜６であり、Ｐ１及びＰ２が一般式（ＰＣ１−ｃ）であり、Ｗ１がＦ、ＣＦ３、ＯＣＦ３、ＣＨ３又はＯＣＨ３であり、ｎ６が１以上であることが好ましい。 Further, Sp 1 , Sp 2 , Q 1 and Q 2 in General Formula (PC1) -3 to General Formula (PC1) -8 are all single bonds, and in n 3 and n 4 , n 3 + n 4 is 3 a to 6, P 1 and P 2 are formula (PC1-c), W 1 is F, a CF 3, OCF 3, CH 3 or OCH 3, is preferably n 6 is 1 or more .
また、一般式（ＰＣ１）におけるＭＧが一般式（ＰＣ１）−９で表される円盤状液晶化合物であることも好ましい Moreover, it is also preferable that MG in the general formula (PC1) is a discotic liquid crystal compound represented by the general formula (PC1) -9.
（式中、Ｒ９３はそれぞれ独立してＰ１−Ｓｐ１−Ｑ１又は一般式（ＰＣ１−ｅ） (In the formula, each R 93 is independently P 1 -Sp 1 -Q 1 or the general formula (PC1-e)
（式中、Ｐ１、Ｓｐ１及びＱ１は一般式（ＰＣ１）と同じ意味を表し、Ｒ９４及びＲ９５はそれぞれ独立して水素原子、ハロゲン原子又はメチル基を表し、Ｒ９６は炭素原子数１〜２０のアルコキシ基を表し、該アルコキシ基中の少なくとも１つの水素原子が前記一般式（ＰＣ１−ａ）〜（ＰＣ１−ｄ）で表される置換基で置換されていてもよい。）の置換基を表す。）
重合性化合物の使用量は好ましくは０．１〜２．０質量％である。
(Wherein P 1 , Sp 1 and Q 1 represent the same meaning as in general formula (PC1), R 94 and R 95 each independently represent a hydrogen atom, a halogen atom or a methyl group, and R 96 represents a carbon atom. Represents an alkoxy group of formula 1 to 20, and at least one hydrogen atom in the alkoxy group may be substituted with a substituent represented by the general formulas (PC1-a) to (PC1-d). Represents a substituent of )
The amount of the polymerizable compound used is preferably 0.1 to 2.0% by mass.
更に、本発明の液晶組成物は、その安定性を向上させるために酸化防止剤を１種又は２種以上含有することもでき、ＵＶ吸収剤を１種又は２種以上含有することもできる。
本発明の液晶組成物を用いた液晶表示素子は高速応答と表示不良の抑制を両立させた有用なものであり、特に、アクティブマトリックス駆動用液晶表示素子に有用であり、ＴＮモード、ＯＣＢモード、ＩＰＳモード、ＦＦＳモード又はＶＡ−ＩＰＳモード用液晶表示素子に適用できる。
上述の重合性化合物を含有する本発明の液晶組成物を用いることで、高分子安定化（ＰＳ）モード液晶表示素子を作製することができる。具体的には、二枚の基板間に重合性化合物を含有する液晶組成物を狭持し、電圧印加下あるいは電圧無印加下で紫外線等のエネルギーによって液晶組成物中の重合性化合物を重合させることで作製することができる。この液晶表示素子においては、重合性化合物の高分子化によって液晶分子の配向状態を記憶化させることができ、それによって配向状態の安定性を向上させることができる。また、応答速度の改善も期待できる。
Furthermore, the liquid crystal composition of the present invention can contain one or more antioxidants in order to improve the stability, and can also contain one or more UV absorbers.
The liquid crystal display device using the liquid crystal composition of the present invention is useful for achieving both high-speed response and suppression of display failure, and is particularly useful for a liquid crystal display device for active matrix driving, including TN mode, OCB mode, It can be applied to a liquid crystal display element for IPS mode, FFS mode or VA-IPS mode.
By using the liquid crystal composition of the present invention containing the polymerizable compound described above, a polymer stabilized (PS) mode liquid crystal display element can be produced. Specifically, a liquid crystal composition containing a polymerizable compound is sandwiched between two substrates, and the polymerizable compound in the liquid crystal composition is polymerized by energy such as ultraviolet rays with or without voltage applied. Can be produced. In this liquid crystal display element, the orientation state of the liquid crystal molecules can be memorized by polymerizing the polymerizable compound, whereby the stability of the orientation state can be improved. In addition, an improvement in response speed can be expected.
以下、例を挙げて本願発明を更に詳述するが、本願発明はこれらによって限定されるものではない。また、以下の実施例及び比較例の組成物における「%」は『質量%』を意味する。 Hereinafter, although an example is given and this invention is further explained in full detail, this invention is not limited by these. Further, “%” in the compositions of the following examples and comparative examples means “mass%”.
液晶組成物の物性として、以下のように表す。
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。
The physical properties of the liquid crystal composition are expressed as follows.
T NI : Nematic phase-isotropic liquid phase transition temperature (° C)
Tn: lower limit temperature of nematic phase (° C)
ε⊥: dielectric constant in the direction perpendicular to the molecular long axis direction at 25 ° C. Δε: dielectric anisotropy at 25 ° C. no: refractive index for ordinary light at 25 ° C. Δn: refractive index anisotropic at 25 ° C. sex
Vth: Applied voltage (V) in a cell having a cell thickness of 6 μm where the transmittance changes by 10% when a rectangular wave with a frequency of 1 KHz at 25 ° C.
η 20 : Bulk viscosity at 20 ° C. (mPa · s)
γ 1 : rotational viscosity (mPa · s)
The following abbreviations are used in compound descriptions.
（実施例１）
以下のような、一般式（ＬＣ３）、一般式（ＬＣ６）及び一般式（ＬＣ７）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。
Example 1
A liquid crystal base composition A composed of the compounds represented by general formula (LC3), general formula (LC6) and general formula (LC7) as shown below was prepared.
以下に、液晶ベース組成物Ａを用いて調製した液晶組成物とその物性値を示す。 The liquid crystal composition prepared using the liquid crystal base composition A and its physical property values are shown below.
（比較例１）
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。
(Comparative Example 1)
The liquid crystal composition prepared using the liquid crystal composition A and its physical property values are shown below.
当該液晶組成物は本願の一般式（ＬＣ２）で表される化合物を含有しない液晶組成物である。実施例１の方がはるかに低粘度であり、γ１も小さく、本発明の組み合わせが非常に優れたものであることがわかる
（実施例２）
以下に、調製した液晶組成物とその物性値を示す。
The liquid crystal composition is a liquid crystal composition not containing the compound represented by the general formula (LC2) of the present application. It can be seen that Example 1 has a much lower viscosity, γ 1 is smaller, and the combination of the present invention is very excellent (Example 2).
The prepared liquid crystal composition and its physical property values are shown below.
（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。
(Example 3)
The prepared liquid crystal composition and its physical property values are shown below.
（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。
Example 4
The prepared liquid crystal composition and its physical property values are shown below.
（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。
(Example 5)
The prepared liquid crystal composition and its physical property values are shown below.
（実施例６）
以下に、調製した液晶組成物とその物性値を示す。
(Example 6)
The prepared liquid crystal composition and its physical property values are shown below.
（実施例７）
以下に、調製した液晶組成物とその物性値を示す。
(Example 7)
The prepared liquid crystal composition and its physical property values are shown below.
（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。
(Example 8)
The prepared liquid crystal composition and its physical property values are shown below.
（実施例９）
以下に、調製した液晶組成物とその物性値を示す。
Example 9
The prepared liquid crystal composition and its physical property values are shown below.
（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。
(Example 10)
The prepared liquid crystal composition and its physical property values are shown below.
このように、実施例２〜１０の液晶組成物は低粘度であり、γ１も小さく、本発明の組み合わせが非常に優れたものであることがわかる。
（実施例１１）
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１０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、１．３９ｖ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。
この実施例３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
Thus, it can be seen that the liquid crystal compositions of Examples 2 to 10 have a low viscosity, γ 1 is small, and the combination of the present invention is very 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. A liquid crystal display device was produced by injecting the liquid crystal composition shown in Example 10 into the empty cell. When the electro-optical characteristics of this display element were measured, the applied voltage at which the transmittance changed by 10% was 1.39 v. 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.
The polymerizable compound represented by the formula (PC-1) -3-1 with respect to 99% of the liquid crystal composition shown in Example 3
を１％添加し均一溶解することにより重合性液晶組成物ＣＬＣ−Ａを調製した。ＣＬＣ−Ａの物性は実施例８で示された液晶組成物の物性とほとんど違いはなかった。
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、１．５８ｖであった。また、５ｖを印加した時の応答速度は４．２ミリ秒であった。また、電圧をオフにした時の応答速度は４．７ミリ秒と、実施例８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。
1% was added and uniformly dissolved to prepare a polymerizable liquid crystal composition CLC-A. The physical properties of CLC-A were almost the same as those of the liquid crystal composition shown in Example 8.
After the CLC-A is sandwiched between the above IPS empty cells, the liquid crystal cell is irradiated with ultraviolet rays by a high-pressure mercury lamp through a filter that cuts ultraviolet rays 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. When the electro-optical characteristics of this display element were measured, 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. In addition, 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 8.
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| JP6061040B2 (en) * | 2013-11-19 | 2017-01-18 | Dic株式会社 | Nematic liquid crystal composition and liquid crystal display device using the same |
| WO2016017615A1 (en) | 2014-07-31 | 2016-02-04 | Dic株式会社 | Nematic liquid crystal composition |
| WO2016017614A1 (en) | 2014-07-31 | 2016-02-04 | Dic株式会社 | Nematic liquid crystal composition |
| WO2018207635A1 (en) * | 2017-05-09 | 2018-11-15 | Dic株式会社 | Composition and liquid crystal display element using this |
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