JP2004323779A - Liquid crystal composition containing compound having five-membered lactone ring skeleton - Google Patents
Liquid crystal composition containing compound having five-membered lactone ring skeleton Download PDFInfo
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- SAXRUMLUKZBSTO-UHFFFAOYSA-N CC(C=C1C)OC1=O Chemical compound CC(C=C1C)OC1=O SAXRUMLUKZBSTO-UHFFFAOYSA-N 0.000 description 1
- IYJMJJJBGWGVKX-UHFFFAOYSA-N CC(CC(C)O1)C1=O Chemical compound CC(CC(C)O1)C1=O IYJMJJJBGWGVKX-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
【0001】
【発明の属する技術分野】
本発明は、電気光学的液晶液晶表示材料として有用な、誘電率異方性が負のネマチック液晶組成物およびそれを用いた液晶表示素子に関する。
【0002】
【従来の技術】
液晶表示素子は、時計、電卓をはじめとしては、家庭用各種電気機器、測定機器、自動車用パネル、ワープロ、電子手帳、プリンター、コンピューター、テレビ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(捩れネマチック)方式やSTN(超捩れネマチック)方式、DS(動的光散乱)方式、GH(ゲスト・ホスト)方式、IPS(インプレインスイッチング)方式、OCB(光学補償複屈折)方式、ECB(電圧制御複屈折)方式、VA(垂直配向)方式、FLC(強誘電性液晶)等をあげることができる。また、駆動方式としても従来のスタティック駆動からマルチプレックス駆動が一般的になり、単純マトリックス方式、最近では、TFT(薄膜トランジスタ)やMIMにより駆動されるAM(アクティブマトリックス)方式が主流になっている。
【0003】
これらの表示方式において、IPS方式、ECB(電圧制御複屈折)方式やVA(垂直配向)方式は、現在汎用のTN方式やSTN方式と異なり、誘電率異方性が負の液晶材料を用いる特徴を有する。これらの中で、VA方式は高速で広視野角の要求される表示素子として、特にテレビ等への応用が現在も友期待されている。
【0004】
これまで、液晶材料はその方式に応じて、非常に多くの化合物が設計・合成されてきたが、VA方式に必要は誘電率異方性が負の液晶材料についてはそれほど多くの化合物が知られているわけではない。実際には2,3−ジフルオロ−1,4−フェニレン基を有する化合物(特許文献1参照)に限られているのが実情である。そのため、Δεの絶対値が十分に大きくないことから低電圧駆動等の特性に問題があった。
【0005】
一方、5員環ラクトン構造を有する液晶化合物は大きな分極率を有し、また光学活性体が合成できることから、FLC方式への応用を目指し多くの化合物が合成されてきたが、VA方式用の誘電率異方性が負の液晶材料として検討されたことはなかった(特許文献2―6参照)。
【0006】
【特許文献1】
特開平7−309857号公報
【特許文献2】
特開昭64−62998号公報
【特許文献3】
特開昭64−244336号公報
【特許文献4】
特開昭65−323710号公報
【特許文献5】
特開昭63−212093号公報
【特許文献6】
特開平7−309857号公報
【0007】
【発明が解決しようとする課題】
本発明が解決しようとする課題は、誘電率異方性が負であって絶対値の大きい液晶組成物を提供し、さらにそれを用いたVA方式用の液晶表示素子を提供することにある。
【0008】
【発明を解決するための手段】
本発明は、上記課題を解決するために鋭意検討した結果、分子内に5員環ラクトン骨格を含む液晶性化合物を少なくとも1種含有し、その誘電率異方性が負であることを特徴とするネマチック液晶組成物及びこれを用いた液晶表示素子を提供する。
【0009】
本発明の液晶組成物は、分子内に5員環ラクトン骨格を含む液晶性化合物を含有するため、分子内に5員環ラクトン骨格を含む液晶性化合物が有する負の誘電率を効率的に用いてVA等の表示方式に使用したときに低電圧駆動を可能とする。
【0010】
【発明の実施の形態】
すなわち、本発明における液晶組成物は、分子内に5員環ラクトン骨格を含む液晶性化合物を少なくとも1種含有するが、一般式(I)または(II)
【化5】
で表される5員環ラクトン骨格を分子内に含む液晶性化合物を少なくとも1種含有することが好ましい。
【0011】
さらに、分子内に5員環ラクトン骨格を含む液晶性化合物が一般式(III)
【化6】
で表される化合物であることがさらに好ましい。
【0012】
ここで、5員環ラクトン骨格(Lact)は先に示した一般式(I)または(II)であるが、中でも(I)が好ましい。(I)の骨格では2つの不斉炭素を有しており、光学活性体となりうるが、ラセミ体が好ましい、また、(I)の骨格ではシス体とトランス体があるが、どちらかまたは混合物でもかまわないが、トランス体が好ましい。
【0013】
R1およびR2はおのおの独立して炭素数1〜10の飽和または不飽和のアルキル基、アルコキシル基、アルカノイルオキシ基またはアルコキシカルボニル基を表すが、炭素数1〜10の飽和または不飽和のアルキル基またはアルコキシル基が好ましい。
【0014】
La〜Ldはおのおの独立して単結合、−CH2CH2−、−CH2O−、−OCH2−、−COO−、−OCO−または−C≡C−を表すが、単結合、−CH2CH2−、−CH2O−、−OCH2−が好ましい。
【0015】
A〜Dはおのおの独立してトランス−1,4−シクロヘキシレン基、トランス−デカヒドロナフタレン−2,6−ジイル基、トランス−1,3−ジオキサン−2,5−ジイル基、1個または2個のフッ素原子で置換されてもよい1,4−フェニレン基、1個または2個のフッ素原子で置換されてもよい1,2,3,4−テトラヒドロナフタレン−2,6−ジイル基または1個から3個のフッ素原子で置換されてもよいナフタレン−2,6−ジイル基を表すが、トランス−1,4−シクロヘキシレン基、トランス−デカヒドロナフタレン−2,6−ジイル基、1個または2個のフッ素原子で置換されてもよい1,4−フェニレン基が好ましく、トランス−1,4−シクロヘキシレン基、1個または2個のフッ素原子で置換されてもよい1,4−フェニレン基が特に好ましい。
n1〜n4はおのおの独立して0または1を表すが、少なくともひとつは1を表すことが好ましい。
5員環ラクトン骨格を含む液晶性化合物の含有量は、液晶性が低下しない範囲でどのような含有率で含んでもよいが、1〜30質量%の範囲が好ましく、1〜20質量%であることがより好ましい。
【0016】
5員環ラクトン骨格を有する化合物以外の第2成分として、一般式(IV)
【化7】
で表される化合物を少なくとも1種類含有することができる。
【0017】
ここで、式中、R3およびR4はおのおの独立して炭素数1〜10の飽和または不飽和のアルキル基またはアルコキシル基を表す。
Y1およびY2はおのおの独立して単結合、−CH2CH2−または−CH2O−を表す。
環Eおよび環Fはトランス−1,4−シクロヘキシレン基、トランス−デカヒドロナフタレン−2,6−ジイル基、1個または2個のフッ素原子で置換されてもよい1,4−フェニレン基を表し、トランス−1,4−シクロヘキシレン基、1個または2個のフッ素原子で置換されてもよい1,4−フェニレン基が好ましい。
mは0〜2の整数を表す。
【0018】
5員環ラクトン骨格を有する化合物以外の第2成分として、一般式(V)
【化8】
で表される化合物を少なくとも1種類含有することができる。
【0019】
ここで、式中、R5およびR6はおのおの独立して水素原子、炭素数1〜10の飽和または不飽和のアルキル基またはアルコキシル基を表すが、炭素数1〜10の飽和または不飽和のアルキル基またはアルコキシル基が好ましい、
Y3は単結合、−CH2CH2−または−CH2O−を表す。
【0020】
環Gおよび環Hはおのおの独立してトランス−1,4−シクロヘキシレン基、トランス−デカヒドロナフタレン−2,6−ジイル基、1または2個のフッ素原子で置換されてもよい1,4−フェニレン基を表すが、トランス−1,4−シクロヘキシレン基、1または2個のフッ素原子で置換されてもよい1,4−フェニレン基が好ましい。
【0021】
Lは1〜3の整数を表すが、1または2が好ましい。
【0022】
本願発明の液晶組成物は、一般式(III)で表される化合物及び一般式(IV)で表される化合物を含有することが好ましく、一般式(III)で表される化合物及び一般式(V)で表される化合物を含有することが好ましく、一般式(III)で表される化合物、一般式(IV)で表される化合物及び一般式(V)で表される化合物を含有することがより好ましい。
【0023】
上記の化合物を含有する液晶組成物は、負の誘電率異方性を示すが、−2より小さいことが好ましく、また、上限温度70℃以上であり、下限温度が−20℃以下であることが好ましい。
【0024】
本発明はさらに本発明の液晶組成物を使用した表示素子を提供するが、アクティブマトリックス用に使用することが好ましく、VA方式に使用することがより好ましい。
【0025】
【実施例】
以下、実施例を挙げて本発明を更に詳述するが、本発明はこれらの実施例に限定されるものではない。液晶表示素子は、セル厚3.5μmのVA−LCD用表示セルを作製し、液晶組成物をこのセルに注入して構成した。
実施例中、測定した特性は以下の通りである。
TN−I :ネマチック相−等方性液体相転移温度(℃)
Δε :誘電異方性(25℃及び1kHz)
Δn :複屈折(20℃及び589nm)
η :粘度(mPa・s)(20℃)
Vth :しきい値電圧(V)(25℃)
【0026】
(実施例1、2及び比較例1) 液晶組成物の調整
以下の液晶組成物(M−1)を作成した。
【化9】
【0027】
実施例1の液晶組成物として、(M−1)の95%と(IIIa)
【化10】
で表される化合物5%からなる液晶組成物(M−2)を調整した。又、実施例2の液晶組成物として、
【0028】
組成物(M−1)の95%と(IIIb)
【化11】
で表される化合物5%からなる液晶組成物(M−3)を調整した。
さらに、(M−1)の90%と(IIIa)5%及び(IIIb)5%からなる液晶組成物(M−4)を調整した。
【0029】
比較例として(M−1)を含めたこれらの液晶組成物の物性を測定しその結果を表1に示す。
【表1】
表1より、実施例1、2及び3は大きい負の誘電率異方性の絶対値を有することがわかる。
本発明の液晶組成物により、優れた表示品位のVA型液晶表示素子を作成することができた。
【0030】
【発明の効果】
本発明により、大きい負の誘電率異方性の絶対値を有する液晶組成物を提供することが可能となった。又、本願発明の液晶組成物はVA型の液晶表示素子の低電圧化に効果的である。[0001]
TECHNICAL FIELD OF THE INVENTION
The present invention relates to a nematic liquid crystal composition having a negative dielectric anisotropy, which is useful as an electro-optical liquid crystal liquid crystal display material, and a liquid crystal display device using the same.
[0002]
[Prior art]
Liquid crystal display elements are used in watches, calculators, home electric appliances, measuring instruments, automobile panels, word processors, electronic notebooks, printers, computers, televisions, and the like. Typical liquid crystal display methods include a TN (twisted nematic) method, an STN (super twisted nematic) method, a DS (dynamic light scattering) method, a GH (guest / host) method, and an IPS (in-plane switching). ), OCB (optically compensated birefringence), ECB (voltage controlled birefringence), VA (vertical alignment), FLC (ferroelectric liquid crystal) and the like. As a driving method, multiplex driving has been generally used instead of conventional static driving, and a simple matrix method, and recently, an AM (active matrix) method driven by a TFT (thin film transistor) or an MIM have become mainstream.
[0003]
In these display modes, the IPS mode, ECB (voltage controlled birefringence) mode and VA (vertical alignment) mode are different from the current general-purpose TN mode and STN mode, and use a liquid crystal material having a negative dielectric anisotropy. Having. Among them, the VA method is currently expected to be applied to a television or the like as a display element requiring a high speed and a wide viewing angle.
[0004]
Until now, a very large number of compounds have been designed and synthesized according to the liquid crystal material. However, so many compounds are required for the liquid crystal material having a negative dielectric anisotropy in the VA method. It is not. Actually, it is actually limited to compounds having a 2,3-difluoro-1,4-phenylene group (see Patent Document 1). Therefore, since the absolute value of Δε is not sufficiently large, there is a problem in characteristics such as low voltage driving.
[0005]
On the other hand, a liquid crystal compound having a 5-membered lactone structure has a large polarizability and an optically active substance can be synthesized. Therefore, many compounds have been synthesized for application to the FLC method. It has never been studied as a liquid crystal material having a negative anisotropy (see Patent Documents 2-6).
[0006]
[Patent Document 1]
JP-A-7-309857 [Patent Document 2]
JP-A-64-62998 [Patent Document 3]
JP-A-64-244336 [Patent Document 4]
JP-A-65-323710 [Patent Document 5]
JP-A-63-212093 [Patent Document 6]
JP-A-7-309857
[Problems to be solved by the invention]
The problem to be solved by the present invention is to provide a liquid crystal composition having a negative dielectric anisotropy and a large absolute value, and further to provide a VA-mode liquid crystal display device using the same.
[0008]
[Means for Solving the Invention]
As a result of intensive studies to solve the above problems, the present invention contains at least one liquid crystal compound having a 5-membered lactone skeleton in a molecule, and has a negative dielectric anisotropy. And a liquid crystal display device using the same.
[0009]
Since the liquid crystal composition of the present invention contains a liquid crystal compound having a 5-membered lactone skeleton in the molecule, the liquid crystal composition of the present invention efficiently uses the negative dielectric constant of the liquid crystal compound having a 5-membered lactone skeleton in the molecule. This enables low-voltage driving when used in a display method such as VA.
[0010]
BEST MODE FOR CARRYING OUT THE INVENTION
That is, the liquid crystal composition of the present invention contains at least one liquid crystal compound having a 5-membered ring lactone skeleton in the molecule, and has the general formula (I) or (II)
Embedded image
It is preferable to contain at least one liquid crystal compound having a 5-membered lactone skeleton represented by the following formula in the molecule.
[0011]
Further, a liquid crystal compound having a 5-membered lactone skeleton in the molecule is represented by the general formula (III):
Embedded image
Further preferred is a compound represented by the formula:
[0012]
Here, the five-membered lactone skeleton (Lact) has the general formula (I) or (II) shown above, but (I) is particularly preferable. The skeleton of (I) has two asymmetric carbons and can be optically active, but a racemic form is preferable. In the skeleton of (I), there are a cis-form and a trans-form, but either one or a mixture is used. However, a trans form is preferred.
[0013]
R 1 and R 2 each independently represent a saturated or unsaturated alkyl group having 1 to 10 carbon atoms, an alkoxyl group, an alkanoyloxy group or an alkoxycarbonyl group, and a saturated or unsaturated alkyl group having 1 to 10 carbon atoms. Groups or alkoxyl groups are preferred.
[0014]
La to Ld each independently represent a single bond, —CH 2 CH 2 —, —CH 2 O—, —OCH 2 —, —COO—, —OCO—, or —C≡C—; CH 2 CH 2 —, —CH 2 O—, and —OCH 2 — are preferred.
[0015]
A to D each independently represent a trans-1,4-cyclohexylene group, a trans-decahydronaphthalene-2,6-diyl group, a trans-1,3-dioxane-2,5-diyl group, one or two 1,4-phenylene group optionally substituted with one fluorine atom, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group optionally substituted with one or two fluorine atoms or 1 Represents a naphthalene-2,6-diyl group which may be substituted with 1 to 3 fluorine atoms, and includes a trans-1,4-cyclohexylene group, a trans-decahydronaphthalene-2,6-diyl group, Alternatively, a 1,4-phenylene group which may be substituted with two fluorine atoms is preferable, and a trans-1,4-cyclohexylene group, and a 1,4-phenylene group which may be substituted with one or two fluorine atoms. Eniren group is particularly preferred.
n 1 to n 4 each independently represent 0 or 1, and preferably at least one represents 1.
The content of the liquid crystal compound containing a 5-membered lactone skeleton may be included at any content within a range where the liquid crystallinity is not reduced, but is preferably in the range of 1 to 30% by mass, and more preferably 1 to 20% by mass. Is more preferable.
[0016]
As the second component other than the compound having a 5-membered lactone skeleton, a compound represented by the general formula (IV)
Embedded image
At least one compound represented by the formula:
[0017]
Here, in the formula, R 3 and R 4 each independently represent a saturated or unsaturated alkyl group or alkoxyl group having 1 to 10 carbon atoms.
Y 1 and Y 2 each independently represent a single bond, —CH 2 CH 2 — or —CH 2 O—.
Ring E and ring F are a trans-1,4-cyclohexylene group, a trans-decahydronaphthalene-2,6-diyl group, a 1,4-phenylene group which may be substituted with one or two fluorine atoms. And a trans-1,4-cyclohexylene group, and a 1,4-phenylene group which may be substituted with one or two fluorine atoms is preferable.
m represents an integer of 0 to 2.
[0018]
As a second component other than the compound having a 5-membered lactone skeleton, a compound represented by the general formula (V):
Embedded image
At least one compound represented by the formula:
[0019]
Here, in the formula, R 5 and R 6 each independently represent a hydrogen atom, a saturated or unsaturated alkyl or alkoxyl group having 1 to 10 carbon atoms, and a saturated or unsaturated 1 to 10 carbon atoms. Alkyl or alkoxyl groups are preferred,
Y 3 represents a single bond, —CH 2 CH 2 — or —CH 2 O—.
[0020]
Ring G and ring H are each independently a trans-1,4-cyclohexylene group, a trans-decahydronaphthalene-2,6-diyl group, and optionally substituted with one or two fluorine atoms. Although it represents a phenylene group, a trans-1,4-cyclohexylene group and a 1,4-phenylene group which may be substituted with one or two fluorine atoms are preferable.
[0021]
L represents an integer of 1 to 3, and is preferably 1 or 2.
[0022]
The liquid crystal composition of the present invention preferably contains the compound represented by the general formula (III) and the compound represented by the general formula (IV), and the compound represented by the general formula (III) and the general formula ( It preferably contains a compound represented by V), and contains a compound represented by general formula (III), a compound represented by general formula (IV) and a compound represented by general formula (V) Is more preferred.
[0023]
The liquid crystal composition containing the above compound exhibits negative dielectric anisotropy, but is preferably smaller than -2, and has an upper limit temperature of 70 ° C or higher and a lower limit temperature of -20 ° C or lower. Is preferred.
[0024]
The present invention further provides a display device using the liquid crystal composition of the present invention, but is preferably used for an active matrix, and more preferably used for a VA system.
[0025]
【Example】
Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited to these Examples. The liquid crystal display element was constructed by preparing a display cell for VA-LCD having a cell thickness of 3.5 μm and injecting a liquid crystal composition into the cell.
The characteristics measured in the examples are as follows.
T NI : Nematic phase-isotropic liquid phase transition temperature (° C.)
Δε: dielectric anisotropy (25 ° C. and 1 kHz)
Δn: birefringence (20 ° C. and 589 nm)
η: viscosity (mPa · s) (20 ° C)
Vth: threshold voltage (V) (25 ° C.)
[0026]
(Examples 1, 2 and Comparative Example 1) Preparation of Liquid Crystal Composition The following liquid crystal composition (M-1) was prepared.
Embedded image
[0027]
As the liquid crystal composition of Example 1, 95% of (M-1) and (IIIa)
Embedded image
A liquid crystal composition (M-2) comprising 5% of the compound represented by the formula was prepared. Further, as the liquid crystal composition of Example 2,
[0028]
95% of the composition (M-1) and (IIIb)
Embedded image
A liquid crystal composition (M-3) consisting of 5% of the compound represented by the formula was prepared.
Further, a liquid crystal composition (M-4) composed of 90% of (M-1), 5% of (IIIa) and 5% of (IIIb) was prepared.
[0029]
Physical properties of these liquid crystal compositions including (M-1) were measured as comparative examples, and the results are shown in Table 1.
[Table 1]
Table 1 shows that Examples 1, 2 and 3 have a large absolute value of negative dielectric anisotropy.
With the liquid crystal composition of the present invention, a VA type liquid crystal display device having excellent display quality could be produced.
[0030]
【The invention's effect】
According to the present invention, it has become possible to provide a liquid crystal composition having a large absolute value of negative dielectric anisotropy. Further, the liquid crystal composition of the present invention is effective for lowering the voltage of a VA liquid crystal display device.
Claims (13)
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JP2003123603A Expired - Fee Related JP4506098B2 (en) | 2003-04-28 | 2003-04-28 | Liquid crystal composition containing a compound having a 5-membered ring lactone skeleton |
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Cited By (1)
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CN106281357A (en) * | 2015-05-21 | 2017-01-04 | 默克专利股份有限公司 | Liquid crystal media and the liquid crystal display comprising it |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0348220A (en) * | 1989-03-14 | 1991-03-01 | Sharp Corp | Ferroelectric liquid crystal element |
JPH03238420A (en) * | 1990-02-15 | 1991-10-24 | Sharp Corp | Ferroelectric liquid crystal element |
JPH04236295A (en) * | 1991-01-18 | 1992-08-25 | Sharp Corp | Ferromagnetic liquid crystal composition and liquid crystal element |
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0348220A (en) * | 1989-03-14 | 1991-03-01 | Sharp Corp | Ferroelectric liquid crystal element |
JPH03238420A (en) * | 1990-02-15 | 1991-10-24 | Sharp Corp | Ferroelectric liquid crystal element |
JPH04236295A (en) * | 1991-01-18 | 1992-08-25 | Sharp Corp | Ferromagnetic liquid crystal composition and liquid crystal element |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN106281357A (en) * | 2015-05-21 | 2017-01-04 | 默克专利股份有限公司 | Liquid crystal media and the liquid crystal display comprising it |
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