JP2022119164A - Compound, liquid crystal composition containing compound, and liquid crystal display device using liquid crystal composition - Google Patents
Compound, liquid crystal composition containing compound, and liquid crystal display device using liquid crystal composition Download PDFInfo
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 88
- 150000001875 compounds Chemical class 0.000 title claims abstract description 79
- 239000000203 mixture Substances 0.000 title claims abstract description 74
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 27
- 125000004429 atom Chemical group 0.000 claims abstract description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 4
- 125000005647 linker group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000000178 monomer Substances 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- -1 methacryloyl group Chemical group 0.000 claims description 7
- 125000000524 functional group Chemical group 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000006850 spacer group Chemical group 0.000 claims description 6
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 230000002459 sustained effect Effects 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 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 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000012071 phase Substances 0.000 description 22
- 230000000052 comparative effect Effects 0.000 description 12
- 230000000704 physical effect Effects 0.000 description 7
- 230000007704 transition Effects 0.000 description 5
- 239000004988 Nematic liquid crystal Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 1
- VLQAJGFBSKQGRC-UHFFFAOYSA-N 2,3-difluoro-4-(4-propylcyclohexyl)phenol Chemical compound C1CC(CCC)CCC1C1=CC=C(O)C(F)=C1F VLQAJGFBSKQGRC-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- XUHFSBSGEAUKBQ-UHFFFAOYSA-N CCOC(C=CC(OCCO)=C1F)=C1F Chemical compound CCOC(C=CC(OCCO)=C1F)=C1F XUHFSBSGEAUKBQ-UHFFFAOYSA-N 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 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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Abstract
Description
本発明は、負の誘電率異方性をもつ化合物、当該化合物を含有する液晶組成物、及び、当該液晶組成物を使用した液晶表示素子に関する。 The present invention relates to a compound having negative dielectric anisotropy, a liquid crystal composition containing the compound, and a liquid crystal display device using the liquid crystal composition.
液晶表示素子は、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、携帯電話、テレビ、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ＭＶＡ（マルチドメイン・バーティカル・アライメント）型、ＰＳＡ（ポリマー・サステインド・アライメント）型、ＩＰＳ（イン・プレーン・スイッチング）型、ＦＦＳ（フリンジ・フィールド・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、低粘性であることが求められている。さらに液晶組成物は個々の表示素子に対して誘電率異方性（Δε）または屈折率異方性（Δｎ）等を要求される値とするなどの観点で、下記特許文献１に示すように、数種類から二十種類程度の化合物から構成されている。 Liquid crystal display elements are used in automobile panels, word processors, electronic notebooks, printers, computers, mobile phones, televisions, advertising display boards, and the like. Typical liquid crystal display methods include TN (twisted nematic) type, STN (super twisted nematic) type, MVA (multi-domain vertical alignment) type using TFT (thin film transistor), PSA ( Polymer Sustained Alignment) type, IPS (In-Plane Switching) type, FFS (Fringe Field Switching) type, and the like. The liquid crystal composition used in these liquid crystal display elements must be stable against external factors such as moisture, air, heat, and light, and must exhibit a liquid crystal phase over as wide a temperature range as possible centering on room temperature, and have a low viscosity. is required to be Further, the liquid crystal composition has dielectric anisotropy (Δε) or refractive index anisotropy (Δn) required for each display element. , consists of several to twenty kinds of compounds.
特に近年においては、高速応答性の液晶組成物が求められている。目的とする物性を達成する為には種々の方法が考えられるが、有効な手段として液晶組成物の低粘性化が挙げられる。液晶組成物の粘性を低下させる為には、粘度（η）の低い化合物を添加する事が極めて有効である。特に回転粘度（γ１）の低い化合物の添加が有効である。しかしながら、従来の粘性の非常に低い化合物は、誘電異方性が０付近の非極性の化合物がほとんどであり、これを多く使用すると誘電異方性が低下してしまう。したがって、所望する誘電異方性を達成するためには、さほど多くは使用できなかった。このことが、特に低粘性の負の誘電率異方性の液晶組成物を作製する際に課題となっていた。 Especially in recent years, there is a demand for liquid crystal compositions with high-speed response. Various methods are conceivable for achieving the desired physical properties, but one effective means is to lower the viscosity of the liquid crystal composition. In order to reduce the viscosity of the liquid crystal composition, it is extremely effective to add a compound having a low viscosity (η). Addition of a compound having a low rotational viscosity (γ 1 ) is particularly effective. However, most of the conventional compounds with very low viscosity are non-polar compounds with a dielectric anisotropy of around 0, and the dielectric anisotropy is lowered when they are used in large amounts. Therefore, not much could be used to achieve the desired dielectric anisotropy. This has been a problem especially when producing a low-viscosity liquid crystal composition with negative dielectric anisotropy.
このため、液晶特性のさらなる向上のために、従来の化合物に比べてより強い負の誘電率異方性を有する化合物の開発が求められている。強い負の誘電率異方性の化合物を少量して、低粘性の非極性化合物を多量使用することにより、所望の負の誘電率異方性をもつ低粘性の液晶組成物が作製できる。例えば、下記特許文献２には、アルキンを含む連結基によって区切られた２つの部位から成り、負の誘電率異方性を有する化合物が開示されている。しかしながら、上述した何れの特許文献に記載の技術によっても、要求される特性は達成されていない。 Therefore, in order to further improve liquid crystal properties, there is a demand for the development of compounds having stronger negative dielectric anisotropy than conventional compounds. A low-viscosity liquid crystal composition having a desired negative dielectric anisotropy can be produced by using a small amount of a compound with a strong negative dielectric anisotropy and a large amount of a low-viscosity nonpolar compound. For example, Patent Document 2 below discloses a compound having two sites separated by a linking group containing an alkyne and having negative dielectric anisotropy. However, the required characteristics have not been achieved by the techniques described in any of the above patent documents.
本発明は、上記事情に鑑みてなされたものであり、従来の化合物に比べて、より強い負の誘電率異方性と低い回転粘度を有する化合物と、その化合物を用いた液晶組成物と、その液晶組成物を用いた液晶表示素子の提供を課題とする。 The present invention has been made in view of the above circumstances, and provides a compound having stronger negative dielectric anisotropy and lower rotational viscosity than conventional compounds, a liquid crystal composition using the compound, An object of the present invention is to provide a liquid crystal display element using the liquid crystal composition.
本発明は、前記課題を解決するために、少なくとも炭素原子をもつ所定のスペーサーによって区切られた２つの部位から成り、スペーサーおよび各々の部位の結合部から、各々の部位の末端へ向かう方向に沿った分子軸がそれぞれ規定され、所定の負の誘電率異方性を有する化合物であって、スペーサーが、１分子中に２つ以上の炭素数をもつメチレンスペーサーであり、各々の部位が、少なくとも２つ以上のフルオロ基を備え、各々の部位の双極子モーメントのベクトル和が、各々の分子軸に対して垂直方向に向かうよう構成され、負の誘電率異方性が－４より強い化合物を提供する。 In order to solve the above problems, the present invention consists of two sites separated by a predetermined spacer having at least carbon atoms, and along the direction from the spacer and the bonding portion of each site to the end of each site a compound having a predetermined negative dielectric anisotropy, the spacer being a methylene spacer having two or more carbon atoms in one molecule, and each site having at least A compound comprising two or more fluoro groups, configured such that the vector sum of the dipole moments of each site is perpendicular to each molecular axis, and having a negative dielectric anisotropy greater than −4 offer.
本発明の特徴は、下記一般式（１）で表される化合物であって、下記一般式（１）において、前述の２つの部位は、連結基Ｘが含むメチレンスペーサーの一端と結合する原子からＲ１を末端とする一連の部位と、連結基Ｘが含むメチレンスペーサーの他端と結合する原子からＲ２を末端とする一連の部位とから成り、下記一般式（１）におけるメチレンスペーサーを含む連結基Ｘは、－(ＣＨ２)n－を表し、ｎは２から１０を表すことにある。 A feature of the present invention is a compound represented by the following general formula (1), in which the two moieties described above are from the atom that bonds to one end of the methylene spacer included in the linking group X Consisting of a series of moieties terminating at R 1 and a series of moieties terminating at R 2 from the atom bonded to the other end of the methylene spacer contained in the linking group X, and including the methylene spacer in the following general formula (1) The linking group X represents -(CH 2 )n-, where n represents 2 to 10.
また、本発明の化合物においては、好ましくは、前記一般式（１）におけるメチレンスペーサーを含む連結基Ｘは、－(ＣＨ２)n－に代えて、－Ｏ－(ＣＨ２)n－Ｏ－を表し、ｎは２を表す。 In the compound of the present invention, preferably, the linking group X containing a methylene spacer in the general formula (1) is -O-(CH 2 )n-O- instead of -(CH 2 )n- and n represents 2.
また、本発明の化合物においては、好ましくは、前記一般式（１）におけるメチレンスペーサーを含む連結基Ｘは、－(ＣＨ２)n－に代えて、－Ｏ－(ＣＨ２)n－Ｏ－を表し、ｎは３から１０を表す。 In the compound of the present invention, preferably, the linking group X containing a methylene spacer in the general formula (1) is -O-(CH 2 )n-O- instead of -(CH 2 )n- and n represents 3 to 10.
また、本発明の化合物においては、好ましくは、前記一般式（１）におけるメチレンスペーサーを含む連結基Ｘは、－(ＣＨ２)n－に代えて、－Ｏ－(ＣＨ２)n－を表し、ｎは２から１０を表す。 In the compound of the present invention, the linking group X containing a methylene spacer in the general formula (1) preferably represents -O-(CH 2 )n- instead of -(CH 2 )n-. , n represents 2 to 10.
また、本発明の化合物においては、好ましくは、前記一般式（１）におけるメチレンスペーサーを含む連結基Ｘは、－(ＣＨ２)n－に代えて、－(ＣＨ２)n－Ｏ－を表し、ｎは２から１０を表す。 In the compound of the present invention, the linking group X containing a methylene spacer in the general formula (1) preferably represents -(CH 2 )n-O- instead of -(CH 2 )n-. , n represents 2 to 10.
また、本発明の化合物においては、好ましくは、前記一般式（１）におけるｂおよびｃは、それぞれ１および０である。もしくは、前記一般式（１）におけるｂおよびｃは、ともに０であってもよい。 In the compound of the present invention, b and c in general formula (1) are preferably 1 and 0, respectively. Alternatively, both b and c in the general formula (1) may be 0.
また、本発明は前述の化合物を一種又は二種以上含有する液晶組成物を提供する。本発明にかかる液晶組成物は、好ましくは、ＵＶ硬化型モノマーを、０．２％から０．５％の割合で更に含有する。 The present invention also provides a liquid crystal composition containing one or more of the above compounds. The liquid crystal composition according to the present invention preferably further contains a UV curable monomer in a proportion of 0.2% to 0.5%.
さらに、本発明は、前記液晶組成物を使用した液晶表示素子を提供する。本発明にかかる液晶表示素子は、好ましくは、ＭＶＡ型、ＰＳＡ型、ＩＰＳ型、又はＦＦＳ型である。 Furthermore, the present invention provides a liquid crystal display device using the liquid crystal composition. The liquid crystal display element according to the present invention is preferably of the MVA type, PSA type, IPS type, or FFS type.
本発明の化合物は、１分子中に２つ以上の炭素数をもつメチレンスペーサーによって区切られた２つの部位から成り、各々の部位に各々の部位に２つ以上のフルオロ基があり、各々の部位における双極子モーメントのベクトル和が分子軸に対して垂直方向に向かう。メチレンスペーサーは自由回転が可能であるので、各々の部位は印加した電場に対してある程度独立して応答する。したがって、本発明の化合物は強い負の誘電率異方性と低い回転粘度を示す。このことにより、要求される液晶組成物の誘電率異方性を達成すべく組成設計する際に、誘電率異方性が０付近の低粘性で低い回転粘度を有する化合物をより多く使用でき、さらに低粘性で低い回転粘度を有する高速応答性の液晶組成物を作製できる。そして、本発明の液晶組成物を使用した液晶表示素子は、特に、高速の応答が要求される液晶テレビや液晶モニター用の液晶表示素子の提供に適している。 The compounds of the present invention consist of two moieties separated by a methylene spacer having two or more carbon atoms in one molecule, each moiety having two or more fluoro groups at each moiety, and each moiety having The vector sum of the dipole moments at is oriented perpendicular to the molecular axis. Since the methylene spacer is free to rotate, each site responds somewhat independently to the applied electric field. Accordingly, the compounds of the present invention exhibit strong negative dielectric anisotropy and low rotational viscosity. As a result, when designing the composition to achieve the required dielectric anisotropy of the liquid crystal composition, it is possible to use more compounds having low rotational viscosity and low viscosity near zero dielectric anisotropy. In addition, a liquid crystal composition having low viscosity and low rotational viscosity can be produced with high speed response. Liquid crystal display elements using the liquid crystal composition of the present invention are particularly suitable for providing liquid crystal display elements for liquid crystal televisions and liquid crystal monitors, which require high-speed response.
以下、本発明について具体的に説明するが、本発明はこれに限定されるものではない。本発明のより好ましき化合物の例として、前記一般式（１）に対応する下記の構造式（１－１）から構造式（１－３０）をあげる。 The present invention will be specifically described below, but the present invention is not limited thereto. As examples of more preferable compounds of the present invention, the following structural formulas (1-1) to (1-30) corresponding to the general formula (1) are given.
前記Ｒ１の好ましきは炭素数１～５のアルキル基又はアルケニル基であり、より好ましくはエチル基又はプロピル基又はエテニル基またはプロペニル基であり、前記Ｒ２の好ましきは炭素数１～５のアルキル基又はアルコキシ基又は３－ブテニル基又は３－ペンテニル基又は２－プロペニルオキシ基又は２－ブテニルオキシ基であり、より好ましきはメチル基又はエチル基又はプロピル基又はメトキシ基又はエトキシ基である。 R 1 is preferably an alkyl group or alkenyl group having 1 to 5 carbon atoms, more preferably an ethyl group, a propyl group, an ethenyl group or a propenyl group, and R 2 is preferably a C 1 to 5 alkyl group or alkoxy group or 3-butenyl group or 3-pentenyl group or 2-propenyloxy group or 2-butenyloxy group, more preferably methyl group or ethyl group or propyl group or methoxy group or ethoxy is the base.
本発明の液晶組成物は、前述の本発明にかかる化合物を一種又は二種以上含有し、前記化合物に加えて、誘電率異方性（以下、単に「Δε」とも称呼する。）が０付近（概ね－２から＋２程度）の従来公知の液晶化合物およびΔεが－３より強い負のΔεを有する従来公知の液晶化合物を含有することが好ましい。 The liquid crystal composition of the present invention contains one or more of the compounds according to the present invention described above, and in addition to the compounds, the dielectric anisotropy (hereinafter also simply referred to as “Δε”) is around 0. (approximately -2 to +2) and a conventionally known liquid crystal compound having a negative Δε greater than -3.
本発明の液晶組成物に含有されるΔεが０付近（概ね－２から＋２程度）の従来公知の好ましき液晶化合物の例として、下記の構造式（２－１）から構造式（２－６）をあげる。このうち一種又は二種以上含有されることが好ましい。 Examples of conventionally known preferred liquid crystal compounds having a Δε of about 0 (approximately −2 to +2) contained in the liquid crystal composition of the present invention include the following structural formulas (2-1) to (2- 6) is given. It is preferable to contain one or two or more of these.
本発明の液晶組成物に含有される－３より強い負のΔεを有する化合物の従来公知の好ましき液晶化合物の例として、下記の構造式（３－１）から構造式（３－６）をあげる。このうち一種又は二種以上含有されることが好ましい。
本発明の液晶組成物を使用した液晶表示素子としては、ＭＶＡ型、ＰＳＡ型、ＩＰＳ型またはＦＦＳ型が好ましい。特に、二枚の基板の間に液晶材料を挟持して液晶を基板に略垂直に配向し、基板に略垂直な電界を印加することにより光学素子や表示素子として使用する垂直配向型のＭＶＡ型とＰＳＡ型が好ましく、液晶を基板に略平行で電極に略垂直に配向するＩＰＳ型とＦＦＳ型にも好ましい。 As a liquid crystal display element using the liquid crystal composition of the present invention, an MVA type, PSA type, IPS type or FFS type is preferable. In particular, a vertically aligned MVA type that is used as an optical element or display element by sandwiching a liquid crystal material between two substrates, aligning the liquid crystal substantially perpendicular to the substrates, and applying an electric field substantially perpendicular to the substrates. and PSA type are preferable, and IPS type and FFS type in which the liquid crystal is aligned substantially parallel to the substrate and substantially perpendicular to the electrodes are also preferable.
本発明の液晶組成物をＰＳＡ型液晶表示素子に使用する場合、本発明の液晶組成物に、０．２％から０．５％の割合でＵＶ硬化型モノマーが含有されていると好ましい。ここにおいて、「０．２％から０．５％の割合」は、複数の化合物が含有された液晶組成物の総重量に対する、当該液晶組成物に含有されるＵＶ硬化型モノマーの重量の割合である。液晶表示素子作製時に、ＵＶ硬化型モノマーを含有する液晶組成物に対して、電圧を印加させながらＵＶを照射することで、重合相を分離して僅かな傾斜配向を安定化する。 When the liquid crystal composition of the present invention is used in a PSA type liquid crystal display device, it is preferable that the liquid crystal composition of the present invention contains 0.2% to 0.5% of a UV curable monomer. Here, the "proportion of 0.2% to 0.5%" is the ratio of the weight of the UV-curable monomer contained in the liquid crystal composition to the total weight of the liquid crystal composition containing a plurality of compounds. be. When a liquid crystal display device is produced, a liquid crystal composition containing a UV-curable monomer is irradiated with UV while a voltage is applied, thereby separating the polymerization phase and stabilizing a slight tilt alignment.
このＵＶ硬化型モノマーは、反応性メソゲンとも呼ばれ、官能基を複数（二つ以上）有する多官能モノマーであることが好ましい。特に、ＵＶ硬化型モノマーが、官能基を２つ又は３つ有し、２つ又は３つの官能基は、メタクリロイル基、アクリロイル基、及び、シンナモイル基のうちの少なくとも１つを含むとより好ましい。 This UV-curable monomer is also called a reactive mesogen, and is preferably a polyfunctional monomer having a plurality (two or more) of functional groups. More preferably, the UV-curable monomer has two or three functional groups, and the two or three functional groups include at least one of a methacryloyl group, an acryloyl group, and a cinnamoyl group.
ＵＶ硬化型モノマーの従来公知の好ましき例として、下記の構造式（５－１）から構造式（５－５）をあげる。このうち一種又は二種以上含有されることが好ましい。
また、本液晶組成物を使用した液晶表示素子は、高速応答を要求される液晶テレビや液晶モニターや低温で高速の応答が要求される車載用ディスプレイやＰＩＤ（パブリック・インフォメーション・ディスプレイ）への応用に適している。 In addition, the liquid crystal display element using this liquid crystal composition is applied to liquid crystal televisions and liquid crystal monitors that require high-speed response, automotive displays and PIDs (public information displays) that require high-speed response at low temperatures. Suitable for
（実施例１）
式（１－１）においてＲ１＝Ｃ３Ｈ７－、Ｒ２＝－ＯＣ２Ｈ５の化合物の合成
(Example 1)
Synthesis of compounds of formula (1-1) where R 1 =C 3 H 7 -, R 2 = -OC 2 H 5
２，３－ジフルオロ－４－（ｔｒａｎｓ－４－プロピルシクロヘキシル）フェノール（５．０４ｇ）、２－（４－エトキシ－２，３－ジフルオロフェニルオキシ）エタノール（２．１６ｇ）及びトリフェニルホスフィン（６．０ｇ）をＴＨＦ（２５ｍＬ）に溶解させ、－１０℃に冷却した。ＤＩＡＤ（４．４ｇ）を、内温が１５℃以上とならない速度で加え、室温にてさらに２時間撹拌した。水（１ｍＬ）を加えて１０分撹拌し、反応液を減圧下濃縮した。ヘキサン（６０ｍＬ）、トルエン（２０ｍＬ）及び７０％ターシャリーブチルヒドロぺルオキシド水溶液（０．８ｇ）を加えて、室温にて１時間撹拌した。析出物を除去し、溶媒を減圧留去した。続いてシリカゲルカラムクロマトグラフィーにより精製し、さらにエタノールから再結晶する事で、式（１－１－１）の化合物を白色固体として５．１ｇ得た。 2,3-difluoro-4-(trans-4-propylcyclohexyl)phenol (5.04 g), 2-(4-ethoxy-2,3-difluorophenyloxy)ethanol (2.16 g) and triphenylphosphine (6 .0 g) was dissolved in THF (25 mL) and cooled to -10°C. DIAD (4.4 g) was added at a rate such that the internal temperature did not rise above 15°C, and the mixture was stirred at room temperature for an additional 2 hours. Water (1 mL) was added, the mixture was stirred for 10 minutes, and the reaction mixture was concentrated under reduced pressure. Hexane (60 mL), toluene (20 mL) and 70% tert-butyl hydroperoxide aqueous solution (0.8 g) were added, and the mixture was stirred at room temperature for 1 hour. The precipitate was removed and the solvent was removed under reduced pressure. Subsequently, the product was purified by silica gel column chromatography and recrystallized from ethanol to obtain 5.1 g of the compound of formula (1-1-1) as a white solid.
式（１－１－１）の化合物は、温度に応じて、結晶相、等方性液体、及び、ネマチック液晶相の何れかの相を呈する。相転移する際の温度が、相転移温度である。式（１－１－１）の各相転移温度は、測定の結果、下記式の通りであった。ここにおいて、Ｃは結晶相、Ｉは等方性液体、Ｎはネマチック液晶相を表す。 The compound of formula (1-1-1) exhibits any one of a crystalline phase, an isotropic liquid phase, and a nematic liquid crystal phase, depending on the temperature. The temperature at which the phase transition occurs is the phase transition temperature. Each phase transition temperature of the formula (1-1-1) was as shown in the following formula as a result of measurement. Here, C represents a crystalline phase, I represents an isotropic liquid, and N represents a nematic liquid crystal phase.
（実施例２）
式（１－２）においてＲ１＝Ｃ３Ｈ７－、Ｒ２＝－ＯＣ２Ｈ５の化合物の合成
(Example 2)
Synthesis of compounds of formula (1-2) where R 1 =C 3 H 7 -, R 2 = -OC 2 H 5
（実施例１）と同様にして、式（１－２－１）の化合物を４．９ｇ得た。
式（１－２－１）の化合物も、温度に応じて、結晶相、等方性液体、及び、ネマチック液晶相の何れかの相を呈する。式（１－２－１）の各相転移温度は、測定の結果、下記式の通りであった。 The compound of formula (1-2-1) also exhibits any one of a crystalline phase, an isotropic liquid phase, and a nematic liquid crystal phase, depending on the temperature. Each phase transition temperature of the formula (1-2-1) was as shown in the following formula as a result of measurement.
（実施例３）
式（１－２６）においてＲ１＝Ｃ３Ｈ７－、Ｒ２＝－ＯＣ２Ｈ５の化合物の合成
(Example 3)
Synthesis of compounds of formula (1-26) where R 1 ═C 3 H 7 —, R 2 ═—OC 2 H 5
（実施例１）と同様にして、式（１－２６－１）の化合物を５．３ｇ得た。
式（１－２６－１）の化合物も、温度に応じて、結晶相、等方性液体、及び、ネマチック液晶相の何れかの相を呈する。式（１－２６－１）の各相転移温度は、測定の結果、下記式の通りであった。 The compound of formula (1-26-1) also exhibits any one of a crystalline phase, an isotropic liquid phase, and a nematic liquid crystal phase, depending on the temperature. Each phase transition temperature of the formula (1-26-1) was as shown in the following formula as a result of measurement.
（実施例４）
式（１－１－１）および式（１－２－１）の本発明の化合物を用いて、表１の液晶組成物（１）（以下、単に「組成物（１）」とも称呼する。）を作製した。表１は、液晶組成物が含有する化合物における組成比率を示している。
(Example 4)
Using the compounds of the present invention represented by formulas (1-1-1) and (1-2-1), liquid crystal composition (1) in Table 1 (hereinafter also simply referred to as "composition (1)"). ) was made. Table 1 shows composition ratios of compounds contained in the liquid crystal composition.
液晶組成物（１）の物性値は以下の通りであった。誘電率異方性（Δε）および屈折率異方性（Δｎ）は２５℃で測定し、粘度（η２０）および回転粘度（γ１）は２０℃で測定した。
ネマチック相上限温度（Ｔｎ－ｉ）：８０．２℃
誘電率異方性（Δε）：－３．３
屈折率異方性（Δｎ）：０．１１
粘度（η２０）：２０．１ｍＰａ・ｓ
回転粘度（γ１）：１２２ｍＰａ・ｓ
The physical property values of the liquid crystal composition (1) were as follows. Dielectric anisotropy (Δε) and refractive index anisotropy (Δn) were measured at 25°C, viscosity (η 20 ) and rotational viscosity (γ 1 ) were measured at 20°C.
Nematic phase upper limit temperature (T ni ): 80.2 °C
Dielectric anisotropy (Δε): -3.3
Refractive index anisotropy (Δn): 0.11
Viscosity (η 20 ): 20.1 mPa·s
Rotational viscosity (γ 1 ): 122 mPa s
（実施例５）
（実施例４）と同様にして、式（１－２－１）および式（１－２６－１）の本発明の化合物を用いて、表１の液晶組成物（２）（以下、単に「組成物（２）」とも称呼する。）を作製した。
(Example 5)
In the same manner as in (Example 4), using the compounds of the present invention of formulas (1-2-1) and (1-26-1), the liquid crystal composition (2) in Table 1 (hereinafter simply " Also referred to as composition (2)”) was prepared.
液晶組成物（２）の物性値は以下の通りであった。
ネマチック相上限温度（Ｔｎ－ｉ）：８０．１℃
誘電率異方性（Δε）：－３．３
屈折率異方性（Δｎ）：０．１１
粘度（η２０）：１７．３ｍＰａ・ｓ
回転粘度（γ１）：１０５ｍＰａ・ｓ
The physical property values of the liquid crystal composition (2) were as follows.
Nematic phase upper limit temperature (T ni ): 80.1 °C
Dielectric anisotropy (Δε): -3.3
Refractive index anisotropy (Δn): 0.11
Viscosity (η 20 ): 17.3 mPa·s
Rotational viscosity (γ 1 ): 105 mPa s
（実施例６）
（実施例５）と同様にして、式（１－２－１）および式（１－２６－１）の本発明の化合物を用いて、表１の液晶組成物（３）（以下、単に「組成物（３）」とも称呼する。）を作製した。
(Example 6)
In the same manner as in (Example 5), using the compounds of the present invention of formulas (1-2-1) and (1-26-1), the liquid crystal composition (3) in Table 1 (hereinafter simply " Also referred to as composition (3)”) was prepared.
液晶組成物（３）の物性値は以下の通りであった。
ネマチック相上限温度（Ｔｎ－ｉ）：８０．３℃
誘電率異方性（Δε）：－３．３
屈折率異方性（Δｎ）：０．１１
粘度（η２０）：１８．０ｍＰａ・ｓ
回転粘度（γ１）：１０３ｍＰａ・ｓ
The physical property values of the liquid crystal composition (3) were as follows.
Nematic phase upper limit temperature (T ni ): 80.3 °C
Dielectric anisotropy (Δε): -3.3
Refractive index anisotropy (Δn): 0.11
Viscosity (η 20 ): 18.0 mPa·s
Rotational viscosity (γ 1 ): 103 mPa s
（比較例１）
（実施例４）の比較例として従来の液晶化合物から成る表１の液晶組成物（４）（以下、単に「組成物（４）」とも称呼する。）を作製した。
(Comparative example 1)
As a comparative example of (Example 4), a liquid crystal composition (4) in Table 1 (hereinafter also simply referred to as "composition (4)") consisting of a conventional liquid crystal compound was prepared.
液晶組成物（４）の物性値は以下の通りであった。
ネマチック相上限温度（Ｔｎ－ｉ）：８０．１℃
誘電率異方性（Δε）：－３．３
屈折率異方性（Δｎ）：０．１１
粘度（η２０）：２３．２ｍＰａ・ｓ
回転粘度（γ１）：１４５ｍＰａ・ｓ
The physical property values of the liquid crystal composition (4) were as follows.
Nematic phase upper limit temperature (T ni ): 80.1 °C
Dielectric anisotropy (Δε): -3.3
Refractive index anisotropy (Δn): 0.11
Viscosity (η 20 ): 23.2 mPa·s
Rotational viscosity (γ 1 ): 145 mPa s
（比較例２）
（実施例５）の比較例として従来の液晶化合物から成る表１の液晶組成物（５）（以下、単に「組成物（５）」とも称呼する。）を作製した。
(Comparative example 2)
As a comparative example of (Example 5), a liquid crystal composition (5) in Table 1 (hereinafter also simply referred to as "composition (5)") consisting of a conventional liquid crystal compound was prepared.
液晶組成物（５）の物性値は以下の通りであった。
ネマチック相上限温度（Ｔｎ－ｉ）：８０．３℃
誘電率異方性（Δε）：－３．３
屈折率異方性（Δｎ）：０．１１
粘度（η２０）：２０．８ｍＰａ・ｓ
回転粘度（γ１）：１４０ｍＰａ・ｓ
The physical property values of the liquid crystal composition (5) were as follows.
Nematic phase upper limit temperature (T ni ): 80.3 °C
Dielectric anisotropy (Δε): -3.3
Refractive index anisotropy (Δn): 0.11
Viscosity (η 20 ): 20.8 mPa·s
Rotational viscosity (γ 1 ): 140 mPa s
（比較例３）
（実施例６）の比較例として従来の液晶化合物から成る表１の液晶組成物（６）（以下、単に「組成物（６）」とも称呼する。）を作製した。
(Comparative Example 3)
As a comparative example of (Example 6), a liquid crystal composition (6) in Table 1 (hereinafter also simply referred to as "composition (6)") consisting of a conventional liquid crystal compound was prepared.
液晶組成物（６）の物性値は以下の通りであった。
ネマチック相上限温度（Ｔｎ－ｉ）：８０．０℃
誘電率異方性（Δε）：－３．３
屈折率異方性（Δｎ）：０．１１
粘度（η２０）：１９．８ｍＰａ・ｓ
回転粘度（γ１）：１１４ｍＰａ・ｓ
The physical property values of the liquid crystal composition (6) were as follows.
Nematic phase upper limit temperature (T ni ): 80.0°C
Dielectric anisotropy (Δε): -3.3
Refractive index anisotropy (Δn): 0.11
Viscosity (η 20 ): 19.8 mPa·s
Rotational viscosity (γ 1 ): 114 mPa s
液晶組成物（１）から（６）は、いずれも液晶テレビ用のＰＳＡ型あるいはＭＶＡ型液晶表示装置に使用される液晶組成物に典型的に要求される特性のうち、ネマチック相上限温度（Ｔｎ－ｉ）＝８０℃、誘電率異方性（Δε）＝－３．３、屈折率異方性（Δｎ）＝０．１１に合わせたものである。さらに、実施例（４）の組成物（１）と比較例（１）の組成物（４）は本発明の化合物以外は同じ液晶化合物から構成されている。同様に、実施例（５）の組成物（２）と比較例（２）の組成物（５）、および実施例（６）の組成物（３）と比較例（３）の組成物（６）もそれぞれ本発明の化合物以外は同じ液晶化合物から構成されている。 Liquid crystal compositions (1) to (6) all have the nematic phase upper limit temperature (T ni )=80° C., dielectric anisotropy (Δε)=−3.3, and refractive index anisotropy (Δn)=0.11. Furthermore, the composition (1) of Example (4) and the composition (4) of Comparative Example (1) are composed of the same liquid crystal compound except for the compound of the present invention. Similarly, composition (2) of Example (5) and composition (5) of Comparative Example (2), and composition (3) of Example (6) and composition (6) of Comparative Example (3) ) are also composed of the same liquid crystal compound except for the compound of the present invention.
表１の式（２－１－１）、式（２－１－２）、式（２－１－３）、式（２－１－４）、式（２－１－５）、式（２－６－１）、および、式（２－３－１）の化合物は下記の化合物を示す。
表１の式（３－１－１）、式（３－１－２）、式（３－５－１）、式（３－５－２）、式（３－３－１）、式（３－３－２）、式（３－４－１）、式（３－４－２）、式（３－４－３）、式（３－６－１）、および、式（３－６－２）の化合物は下記の化合物を示す。
表１の式（４－１－１）および（４－１－２）の化合物は下記の化合物を示す。
実施例（４）の組成物（１）の回転粘度（γ１）は１２２ｍＰａ・ｓと比較例（１）の組成物（４）の回転粘度（γ１）１４５ｍＰａ・ｓより明らかに低くなっている。同様に、実施例（５）の組成物（２）の回転粘度は１０５ｍＰａ・ｓと比較例（２）の１４０ｍＰａ・ｓより低くなっており、実施例（６）の組成物（３）の回転粘度も１０３ｍＰａ・ｓと比較例（３）の１１４ｍＰａ・ｓより低くなっている。これらのことから、本発明の液晶化合物およびその液晶組成物は高速応答性に有効であることは明白である。 The rotational viscosity (γ 1 ) of the composition (1) of Example (4) was 122 mPa·s, which was clearly lower than the rotational viscosity (γ 1 ) of 145 mPa·s of the composition (4) of Comparative Example ( 1 ). there is Similarly, the rotational viscosity of composition (2) of Example (5) was 105 mPa s, which was lower than 140 mPa s of Comparative Example (2), and the rotational viscosity of composition (3) of Example (6) was 105 mPa s. The viscosity is also 103 mPa·s, which is lower than 114 mPa·s of Comparative Example (3). From these facts, it is clear that the liquid crystal compound and the liquid crystal composition of the present invention are effective for high-speed response.
Claims (17)
前記スペーサーは、
１分子中に２つ以上の炭素数をもつメチレンスペーサーであり、
各々の前記部位は、
少なくとも２つ以上のフルオロ基を備え、各々の前記部位の双極子モーメントのベクトル和が、各々の前記分子軸に対して垂直方向に向かうよう構成され、
前記負の誘電率異方性は、－４より強い化合物において、
下記の一般式（１）
（式中、Ｒ１およびＲ２は炭素原子数１から９のアルキル基又はアルコキシ基又は炭素原子数２から９のアルケニル基又はアルケニルオキシ基を表し、ａおよびｄは０、１、又は２を表し、ｂおよびｃは０または１を表し、環Ａおよび環Ｂは、下記の構造式（a－１）から構造式（a－４）のうちのいずれかを表し、
２つの前記部位は、
前記一般式（１）において、前記連結基Ｘが含む前記メチレンスペーサーの一端と結合する原子から前記Ｒ１を末端とする一連の部位と、前記連結基Ｘが含む前記メチレンスペーサーの他端と結合する原子から前記Ｒ２を末端とする一連の部位と、から成り、
前記一般式（１）における前記メチレンスペーサーを含む前記連結基Ｘは、
－(ＣＨ２)n－を表し、ｎは２から１０を表すことを特徴とする化合物。 consisting of two sites separated by a given spacer having at least a carbon atom, wherein a molecular axis is defined along a direction from the bonding portion of the spacer and each of the sites to the end of each of the sites, and A compound having a negative dielectric anisotropy of
The spacer is
A methylene spacer having two or more carbon atoms in one molecule,
each of the said sites,
comprising at least two fluoro groups, wherein the vector sum of the dipole moments of each of the moieties is oriented perpendicular to each of the molecular axes;
The negative dielectric anisotropy is stronger than -4 in the compound,
General formula (1) below
(wherein R 1 and R 2 represent an alkyl group or alkoxy group having 1 to 9 carbon atoms or an alkenyl group or alkenyloxy group having 2 to 9 carbon atoms, and a and d represent 0, 1, or 2; wherein b and c represent 0 or 1, ring A and ring B represent any one of the following structural formulas (a-1) to (a-4),
The two said parts are
In the general formula (1), a series of sites from the atom bonded to one end of the methylene spacer included in the linking group X to the end of the R 1 and the other end of the methylene spacer included in the linking group X are linked. and a series of moieties from the atom to the end of the R 2 ,
The linking group X containing the methylene spacer in the general formula (1) is
A compound characterized in that it represents -(CH 2 )n-, wherein n represents 2 to 10.
－(ＣＨ２)n－に代えて、－Ｏ－(ＣＨ２)n－Ｏ－を表し、ｎは２を表す請求項１に記載の化合物。 The linking group X containing the methylene spacer in the general formula (1) is
2. A compound according to claim 1, wherein -(CH 2 )n- is replaced by -O-(CH 2 )n-O-, where n is 2.
－(ＣＨ２)n－に代えて、－Ｏ－(ＣＨ２)n－Ｏ－を表し、ｎは３から１０を表す請求項１に記載の化合物。 The linking group X containing the methylene spacer in the general formula (1) is
2. A compound according to claim 1, wherein -(CH 2 )n- is replaced by -O-(CH 2 )n-O-, where n is 3-10.
－(ＣＨ２)n－に代えて、－Ｏ－(ＣＨ２)n－を表し、ｎは２から１０を表す請求項１に記載の化合物。 The linking group X containing the methylene spacer in the general formula (1) is
2. A compound according to claim 1, wherein -(CH 2 )n- is replaced by -O-(CH 2 )n-, where n is 2-10.
－(ＣＨ２)n－に代えて、－(ＣＨ２)n－Ｏ－を表し、ｎは２から１０を表す請求項１に記載の化合物。 The linking group X containing the methylene spacer in the general formula (1) is
2. A compound according to claim 1, wherein -(CH 2 )n- is replaced by -(CH 2 )n-O-, where n is 2-10.
それぞれ１および０である請求項１から請求項５のいずれか一項に記載の化合物。 The b and the c in the general formula (1) are
6. A compound according to any one of claims 1 to 5 which is 1 and 0 respectively.
各々独立して－ＣＨ２Ｏ－、－ＯＣＨ２－、－ＣＯＯ－、－ＯＣＯ－、－Ｃ≡Ｃ－、又は単結合である請求項１から請求項６のいずれか一項に記載の化合物。 The Z 1 and the Z 2 in the general formula (1) are
7. The compound of any one of claims 1 to 6, wherein each independently -CH 2 O-, -OCH 2 -, -COO-, -OCO-, -C≡C-, or a single bond .
単結合である請求項７に記載の化合物。 The Z 1 and the Z 2 in the general formula (1) are
8. The compound of claim 7, which is a single bond.
前記構造式（ａ－１）のシクロヘキサン環、又は、前記構造式（ａ－２）のベンゼン環である請求項１から請求項８のいずれか一項に記載の化合物。 The ring A and the ring B in the general formula (1) are
9. The compound according to any one of claims 1 to 8, which is a cyclohexane ring of the structural formula (a-1) or a benzene ring of the structural formula (a-2).
下記の構造式（３－１）から構造式（３－６）
更に含有する請求項１０の液晶組成物。 Structural formulas (2-1) to (2-6) below
Structural formula (3-6) from the following structural formula (3-1)
11. The liquid crystal composition according to claim 10, further comprising:
エチル基、プロピル基、エテニル基、又はプロペニル基であり、
前記構造式（２－１）から前記構造式（２－６）における前記Ｒ４は、
炭素原子数１から５のアルキル基、又はアルコキシ基であり、
前記構造式（３－１）から前記構造式（３－６）における前記Ｒ５は、
エチル基、プロピル基、エテニル基、又はプロペニル基であり、
前記構造式（３－１）から前記構造式（３－６）における前記Ｒ６は、
メチル基、又はエチル基である請求項１１の液晶組成物。 The R 3 in the structural formulas (2-1) to (2-6) is
an ethyl group, a propyl group, an ethenyl group, or a propenyl group,
The R 4 in the structural formulas (2-1) to (2-6) is
an alkyl group having 1 to 5 carbon atoms or an alkoxy group,
The R 5 in the structural formulas (3-1) to (3-6) is
an ethyl group, a propyl group, an ethenyl group, or a propenyl group,
The R 6 in the structural formulas (3-1) to (3-6) is
12. The liquid crystal composition according to claim 11, which is a methyl group or an ethyl group.
０．２％から０．５％の割合で更に含有する請求項１０から請求項１２のいずれか一項の液晶組成物。 UV curable monomer having multiple functional groups,
13. The liquid crystal composition according to any one of claims 10 to 12, further comprising 0.2% to 0.5%.
２つ又は３つの前記官能基は、
メタクリロイル基、アクリロイル基、及び、シンナモイル基のうちの少なくとも１つを含む請求項１３の液晶組成物。 The UV-curable monomer has two or three functional groups,
Two or three of said functional groups are
14. The liquid crystal composition of Claim 13, comprising at least one of a methacryloyl group, an acryloyl group, and a cinnamoyl group.
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