JP2000336364A - Liquid crystal composition and liquid crystal display device - Google Patents

Liquid crystal composition and liquid crystal display device

Info

Publication number
JP2000336364A
JP2000336364A JP11153717A JP15371799A JP2000336364A JP 2000336364 A JP2000336364 A JP 2000336364A JP 11153717 A JP11153717 A JP 11153717A JP 15371799 A JP15371799 A JP 15371799A JP 2000336364 A JP2000336364 A JP 2000336364A
Authority
JP
Japan
Prior art keywords
group
liquid crystal
general formula
carbon atoms
compounds
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
JP11153717A
Other languages
Japanese (ja)
Other versions
JP4505879B2 (en
Inventor
Shinji Ogawa
真治 小川
Hiroyuki Onishi
博之 大西
Haruyoshi Takatsu
晴義 高津
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DIC Corp
Original Assignee
Dainippon Ink and Chemicals Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dainippon Ink and Chemicals Co Ltd filed Critical Dainippon Ink and Chemicals Co Ltd
Priority to JP15371799A priority Critical patent/JP4505879B2/en
Publication of JP2000336364A publication Critical patent/JP2000336364A/en
Application granted granted Critical
Publication of JP4505879B2 publication Critical patent/JP4505879B2/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Abstract

PROBLEM TO BE SOLVED: To obtain the subject composition causing no decline in both contrast and responsiveness, improved in the temperature dependency of drive voltage along and capable of suppressing electric current levels by combining each specific liquid crystal compounds. SOLUTION: This liquid crystal composition comprises (A) pref. 5-40 wt.% of a 1st component comprising at least one kind of compound of formula I (R1 is a 1-16C alkyl or alkoxyl, 2-16C alkenyl or the like) and (B) pref. 5-40 wt.% of a 2nd component comprising one or more kinds of compound of respective formulas II and III [R2 to R4 are each a (F-substituted) 1-16C alkyl or alkoxyl or the like; rings A to E are each trans-1,4-cyclohexylene or the like; l and m are each 0, 1 or 2; Z1 to Z4 are each a single bond, CH2CH2 or the like; X1 and X3 are each H, F or the like; X2 is cyano, F or the like], being >=75 deg.C in nematic phase upper limit temperature and 0.07-0.18 in refractive index anisotropy (Δn).

Description

【発明の詳細な説明】DETAILED DESCRIPTION OF THE INVENTION

【0001】[0001]

【発明の属する技術分野】本発明は、電気光学的液晶表
示材料として有用なネマチック液晶組成物及びこれを用
いた液晶表示素子に関する。
BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a nematic liquid crystal composition useful as an electro-optical liquid crystal display material and a liquid crystal display device using the same.

【0002】[0002]

【従来の技術】液晶表示装置(LCD)は、電卓のディス
プレイとして登場して以来、コンピューターの開発と歩
みを同じくして、TN-LCD(捻れネマチック液晶表示装
置)から、STN-LCDへと表示容量の拡大に対応してき
た。STN-LCDは、シェファー(Scheffer)等[SID '85 D
igest, 120頁(1985年)]、あるいは衣川等[SID '86 Di
gest,122頁(1986年)]によって開発され、ワードプロセ
ッサ、パーソナルコンピュータなどの高情報処理用の表
示に広く普及しはじめている。最近、STN-LCDでの応答
特性を改善する目的でアクティブアドレッシング駆動方
式が提案されている。(Proc.12th International Disp
lay Research Conference p.503 1992年)また、携帯用
端末表示(Personal Digital Assistance)ではより広
い温度域で良好な表示特性が要求されている。この様な
液晶材料として粘性が低く、駆動電圧が低くなおかつ広
い温度範囲に対して一定値を保持することや、あるいは
種々の時分割に対応した周波数範囲で駆動電圧が変動し
ないことが要求されている。しかし、表示素子に組み込
んだときの応答速度やコントラストなどはまだ十分とは
言えず、現在も新しい液晶化合物あるいは液晶組成物の
提案がなされている。
2. Description of the Related Art Since liquid crystal displays (LCDs) have appeared as calculator displays, they have progressed from computer development to TN-LCDs (twisted nematic liquid crystal displays) to STN-LCDs. It has responded to the expansion of capacity. STN-LCD is based on Scheffer and others [SID '85 D
igest, 120 (1985)] or Kinukawa et al. [SID '86 Di
gest., page 122 (1986)], and has begun to be widely used in displays for high information processing such as word processors and personal computers. Recently, an active addressing drive method has been proposed for the purpose of improving the response characteristics of an STN-LCD. (Proc. 12th International Disp
lay Research Conference p.503 1992) In addition, portable terminal displays (Personal Digital Assistance) require good display characteristics over a wider temperature range. Such a liquid crystal material is required to have a low viscosity, a low driving voltage and a constant value over a wide temperature range, or a driving voltage that does not fluctuate in a frequency range corresponding to various time divisions. I have. However, the response speed and contrast when incorporated into a display element cannot be said to be sufficient, and new liquid crystal compounds or liquid crystal compositions have been proposed at present.

【0003】[0003]

【発明が解決しようとする課題】上述のようにTN-LCDや
STN-LCDの重要な特性改善課題の一つにコントラストの
向上がある。LCDの急速な用途拡大に伴い、室内で使用
されるだけでなく、コンピューターの携帯端末ディスプ
レイ、車載用計器、屋外使用計測機のディスプレイのよ
うに、温度条件の過酷な屋外で使用されることが増加し
てきた。LCDが置かれる環境の温度変化による表示コン
トラストの低下が問題になってきている。この周囲の温
度変化によるLCD表示品位の低下の原因は、閾値電圧Vth
の温度依存性に起因するところが大きい。
As described above, TN-LCD and
One of the important characteristics improvement issues of STN-LCD is to improve the contrast. With the rapid expansion of applications of LCDs, LCDs are not only used indoors, but are also used outdoors where temperature conditions are severe, such as displays for computer portable terminals, in-vehicle instruments, and outdoor measuring instruments. Has increased. The decrease in display contrast due to a change in the temperature of the environment in which the LCD is placed has become a problem. The cause of the deterioration of LCD display quality due to this ambient temperature change is the threshold voltage Vth
Is largely attributable to the temperature dependence.

【0004】閾値電圧Vthの温度変化の原因としては、
ネマティック液晶の弾性定数・誘電率などの温度変化と
添加したカイラル物質の固有ピッチの温度変化が考えら
れる。カイラル物質の固有ピッチの温度変化を制御する
ことにより、閾値電圧の温度依存性を改善する提案は既
に行われている(特開昭55-38869号公報に記載)。しか
し、母体液晶とカイラル物質の組み合わせにより、その
効果が変化する事や、カイラル量を増やすことにより、
レスポンス等の表示特性に悪影響を及ぼすことが問題に
なっていた。また、液晶中に含まれるイオン性物質の易
動度の温度変化により電流値が増加するため、液晶にか
かる実効値電圧がイオンにより消費され、コントラスト
が低下する現象が起こっているため、電流値の抑制がコ
ントラストの改善には重要な因子となる。
The cause of the temperature change of the threshold voltage Vth is as follows.
It is conceivable that the temperature change such as the elastic constant and the dielectric constant of the nematic liquid crystal and the temperature change of the specific pitch of the added chiral substance. A proposal for improving the temperature dependency of the threshold voltage by controlling the temperature change of the specific pitch of the chiral substance has already been made (described in JP-A-55-38869). However, depending on the combination of the base liquid crystal and the chiral substance, the effect changes, and by increasing the amount of chiral,
There has been a problem that display characteristics such as response are adversely affected. In addition, since the current value increases due to the temperature change of the mobility of the ionic substance contained in the liquid crystal, the effective value voltage applied to the liquid crystal is consumed by the ions, and the contrast is reduced. Is an important factor in improving the contrast.

【0005】本発明が解決しようとする課題は、コント
ラストやレスポンスを低下させることなく、駆動電圧の
温度依存性を改善し、同時に電流値を抑制した組成物を
提供すること、また、この液晶組成物を使用した液晶表
示素子を提供することにある。
An object of the present invention is to provide a composition in which the temperature dependence of the driving voltage is improved without lowering the contrast and response, and at the same time, the current value is suppressed. It is to provide a liquid crystal display element using a product.

【0006】[0006]

【課題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、種々の液晶化合物を用いた液晶組成物を
検討した結果以下の液晶組成物を見いだした。
Means for Solving the Problems In order to solve the above-mentioned problems, the present invention has examined the liquid crystal compositions using various liquid crystal compounds, and has found the following liquid crystal compositions.

【0007】発明1.第一成分として、一般式(I)Invention 1 As the first component, general formula (I)

【0008】[0008]

【化8】 [Formula 8]

【0009】(式中、R1は、炭素原子数1〜16のアルキ
ル基またはアルコキシル基、炭素原子数2〜16のアルケ
ニル基、炭素原子数3〜16のアルケニルオキシ基、また
は炭素原子数1〜10のアルコキシル基で置換された炭素
原子数1〜12のアルキル基を表す。)から選ばれる化合
物を1種もしくは2種以上を含有し、第二成分として、一
般式(II)、(III)
Wherein R 1 is an alkyl or alkoxyl group having 1 to 16 carbon atoms, an alkenyl group having 2 to 16 carbon atoms, an alkenyloxy group having 3 to 16 carbon atoms, or Represents an alkyl group having 1 to 12 carbon atoms substituted with an alkoxyl group having from 1 to 10), and as a second component, a compound represented by the general formula (II) or (III )

【0010】[0010]

【化9】 [Formula 9]

【0011】(式中、R2、R3、R4は、それぞれ独立的
に、フッ素置換されていても良い炭素原子数1〜16のア
ルキル基またはアルコキシル基、炭素原子数2〜16のア
ルケニル基、炭素原子数3〜16のアルケニルオキシ基、
または炭素原子数1〜10のアルコキシル基で置換された
炭素原子数1〜12のアルキル基を表し、環A、環B、環C、
環D及び環Eは、それぞれ独立的に、フッ素原子により置
換されていてもよい1,4-フェニレン基、2-メチル-1,4-
フェニレン基、3-メチル-1,4-フェニレン基、2,6-ナフ
チレン基、2,7-フェナントリレン基、2,7-フルオレン
基、トランス-1,4-シクロヘキシレン基、2,6-テトラリ
ン基、2,6-デカリン基、トランス-1,3ジオキサン-2,5-
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-ジイル基またはピリダジン-2,5-
ジイル基を表し、l、mは、それぞれ独立的に、0、1もし
くは2を表し、Z1、Z2、Z3、Z4は、それぞれ独立的に、
単結合、-CH2CH2-、-(CH2)4-、-OCH2-、-CH2O-または-C≡C
-表し、X2はシアノ基、フッ素原子、塩素原子、トリフ
ルオロメトキシ基、トリフルオロメチル基、ジフルオロ
メトキシ基、水素原子、3,3,3-トリフルオロエトキシ
基、R'または-OR'を表し、R'は炭素原子数1〜12の直鎖
状アルキル基または炭素原子数2〜12の直鎖状アルケニ
ル基を表し、X1、X3は、それぞれ独立的に、水素原子、
フッ素原子または塩素原子を表す。ただし、環Dがピリ
ミジン-2,5-ジイル基、m=0及びZ4が単結合である場合、
X 1、X3が同時にフッ素原子ではなく、X2がR'または-OR'
を表す場合、X1、X3は同時に水素原子ではない。)から
選ばれる化合物を1種もしくは2種以上を含有し、なおか
つネマチック相上限温度が75℃以上であり、屈折率の異
方性(Δn)が0.07〜0.18の範囲であることを特徴とす
る液晶組成物。
(Where RTwo, RThree, RFourAre independent
In addition, an atom having 1 to 16 carbon atoms which may be
Alkyl or alkoxyl group, C 2 -C 16
Alkenyl group, alkenyloxy group having 3 to 16 carbon atoms,
Or substituted with an alkoxyl group having 1 to 10 carbon atoms
Represents an alkyl group having 1 to 12 carbon atoms, ring A, ring B, ring C,
Ring D and ring E are each independently replaced by a fluorine atom
Optionally substituted 1,4-phenylene group, 2-methyl-1,4-
Phenylene group, 3-methyl-1,4-phenylene group, 2,6-naph
Tylene group, 2,7-phenanthrylene group, 2,7-fluorene
Group, trans-1,4-cyclohexylene group, 2,6-tetrali
Group, 2,6-decalin group, trans-1,3 dioxane-2,5-
Diyl group, pyridine-2,5-diyl group, pyrimidine-2,5-di
Yl, pyrazine-2,5-diyl or pyridazine-2,5-
Represents a diyl group, and l and m are each independently 0, 1 or
Or 2 and Z1, ZTwo, ZThree, ZFourAre, independently of each other,
Single bond, -CHTwoCHTwo-,-(CHTwo)Four-, -OCHTwo-, -CHTwoO- or -C≡C
-Represent, XTwoIs a cyano group, a fluorine atom, a chlorine atom,
Fluoromethoxy group, trifluoromethyl group, difluoro
Methoxy group, hydrogen atom, 3,3,3-trifluoroethoxy
Represents a group, R ′ or —OR ′, wherein R ′ is a straight chain having 1 to 12 carbon atoms.
Alkyl group or linear alkenyl having 2 to 12 carbon atoms
X1, XThreeIs independently a hydrogen atom,
Represents a fluorine atom or a chlorine atom. However, if ring D is
Midine-2,5-diyl group, m = 0 and ZFourIs a single bond,
X 1, XThreeIs not simultaneously a fluorine atom, but XTwoIs R 'or -OR'
To represent X1, XThreeAre not simultaneously hydrogen atoms. From)
Contains one or more selected compounds,
The maximum temperature of the nematic phase is 75 ° C or higher, and
Characterized in that the anisotropy (Δn) is in the range of 0.07 to 0.18
Liquid crystal composition.

【0012】発明2.第一成分として、一般式(I)の化合
物を1種もしくは2種以上を含有し、その含有率が5〜40
重量%の範囲で、さらに第二成分として、一般式(II)、
一般式(III)の化合物の中から選んだ1種もしくは2種以
上を含有し、選んだ化合物の含有率がそれぞれ5〜40重
量%の範囲であることを特徴とする発明1記載の液晶組成
物。
Invention 2. As the first component, one or more compounds of the general formula (I) are contained, and the content is 5 to 40.
% By weight, and as a second component, a general formula (II):
The liquid crystal composition according to Invention 1, wherein the liquid crystal composition contains one or more selected from compounds of the general formula (III), and the content of each of the selected compounds is in the range of 5 to 40% by weight. object.

【0013】発明3.一般式(II)の化合物として、環Aお
よび環Bがトランス-1,4-シクロヘキシレン基であり、
Z1、Z2が単結合の一般式(II-a)
Invention 3 As the compound of the general formula (II), Ring A and Ring B are trans-1,4-cyclohexylene groups,
General formula (II-a) in which Z 1 and Z 2 are single bonds

【0014】[0014]

【化10】 [Formula 10]

【0015】(式中、R5、R6は、R2、R3と同じ意味を表
し、環Fは、1,4-フェニレン基またはトランス-1,4-シク
ロヘキシレン基を表し、nは、0もしくは1を表す。)か
ら選ばれる1種もしくは2種以上の化合物を含有すること
を特徴とする発明1又は2記載の液晶組成物。
(Wherein, R 5 and R 6 have the same meanings as R 2 and R 3 , ring F represents a 1,4-phenylene group or a trans-1,4-cyclohexylene group, and n represents , 0 or 1.) The liquid crystal composition according to invention 1 or 2, comprising one or more compounds selected from the group consisting of:

【0016】発明4.第一成分として、一般式(I)の化
合物を1種もしくは2種以上を含有し、その含有率が5〜4
0重量%の範囲で、なおかつ第二成分として、一般式(II-
a)の化合物を1種もしくは2種以上を含有し、その含有率
が5〜40重量%の範囲であることを特徴とする発明3記載
の液晶組成物。
Invention 4. As the first component, one or more compounds of the general formula (I) are contained, and the content thereof is 5 to 4
In the range of 0% by weight and as the second component, the compound represented by the general formula (II-
3. The liquid crystal composition according to Invention 3, wherein the liquid crystal composition contains one or more kinds of the compound (a), and the content thereof is in the range of 5 to 40% by weight.

【0017】発明5.一般式(III)の化合物として、環D
がトランス-1,4-シクロヘキシレン基であり、Z3、Z4
単結合であり、m=1の一般式(III-a)
Invention 5 As a compound of the general formula (III), ring D
Is a trans-1,4-cyclohexylene group, Z 3 and Z 4 are a single bond, and m = 1 is a general formula (III-a)

【0018】[0018]

【化11】 [Formula 11]

【0019】(式中、R7は、炭素原子数1〜8のアルキル
基または炭素原子数2〜8のアルケニル基を表し、環G
は、1,4-フェニレン基またはトランス-1,4-シクロヘキ
シレン基を表し、X5は、シアノ基、フッ素原子、トリフ
ルオロメトキシ基、ジフルオロメトキシ基を表し、X4
X6は、それぞれ独立的に、水素原子またはフッ素原子を
表す。)から選ばれる1種もしくは2種以上の化合物を含
有することを特徴とする発明1又は2記載の液晶組成物。
(Wherein R 7 represents an alkyl group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms;
Represents a 1,4-phenylene group or trans-1,4-cyclohexylene group, X 5 represents a cyano group, a fluorine atom, a trifluoromethoxy group, a difluoromethoxy group, X 4 ,
X 6 each independently represents a hydrogen atom or a fluorine atom. 3. The liquid crystal composition according to the invention 1 or 2, comprising one or more compounds selected from the group consisting of:

【0020】発明6.第一成分として、一般式(I)の化
合物を1種もしくは2種以上を含有し、その含有率が5〜4
0重量%の範囲で、なおかつ一般式(III-a)の化合物を1種
もしくは2種以上を含有し、その含有率が5〜40重量%の
範囲であることを特徴とする発明5記載の液晶組成物。
Invention 6 As the first component, one or more compounds of the general formula (I) are contained, and the content thereof is 5 to 4
In the range of 0% by weight, and containing one or more compounds of the general formula (III-a), the content of the invention 5 characterized in that the content is in the range of 5 to 40% by weight Liquid crystal composition.

【0021】発明7.一般式(I)の化合物を1種もしく
は2種以上を含有し、その含有率が5〜40重量%の範囲
で、なおかつ一般式(II-b)
Invention 7 One or more compounds of the general formula (I) are contained, the content of which is in the range of 5 to 40% by weight, and the compound of the general formula (II-b)

【0022】[0022]

【化12】 Embedded image

【0023】(式中、R8、R9は、それぞれ独立的に、炭
素原子数1〜8のアルキル基または炭素原子数2〜8のアル
ケニル基を表す。)から選ばれる1種もしくは2種以上の
化合物を含有し、その含有率が5〜40重量%の範囲で、さ
らに一般式(II-c)
Wherein R 8 and R 9 each independently represent an alkyl group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms. Containing the above compound, the content of which is in the range of 5 to 40% by weight, further represented by the general formula (II-c)

【0024】[0024]

【化13】 Embedded image

【0025】(式中、R10、R11は、それぞれ独立的に、
炭素原子数1〜8のアルキル基または炭素原子数2〜8のア
ルケニル基を表す。)から選ばれる1種もしくは2種以上
の化合物を含有し、その含有率が5〜40重量%の範囲であ
ることを特徴とする発明1〜6記載の液晶組成物。
(Wherein R 10 and R 11 are each independently:
Represents an alkyl group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms. 7.) The liquid crystal composition according to any one of inventions 1 to 6, comprising one or more compounds selected from the group consisting of (1) and (2), and the content thereof is in the range of 5 to 40% by weight.

【0026】発明8.一般式(III)もしくは(III-a)とし
て、一般式(III-b)
Invention 8. As the general formula (III) or (III-a), the general formula (III-b)

【0027】[0027]

【化14】 Embedded image

【0028】(式中、R12は、炭素原子数1〜16のアルキ
ル基または炭素原子数2〜8のアルケニル基を表す。)か
ら選ばれる1種もしくは2種以上の化合物を含有し、その
含有率が5〜40重量%の範囲であることを特徴とする発明
1〜7記載の液晶組成物。
Wherein R 12 represents one or more compounds selected from the group consisting of an alkyl group having 1 to 16 carbon atoms and an alkenyl group having 2 to 8 carbon atoms. The invention characterized in that the content is in the range of 5 to 40% by weight.
8. The liquid crystal composition according to 1 to 7.

【0029】発明9.発明1〜8記載の液晶組成物を用い
た液晶表示素子。
Invention 9 A liquid crystal display device using the liquid crystal composition according to any one of Inventions 1 to 8.

【0030】発明10.発明1〜8記載の液晶組成物を用い
た、ねじれ角が220°〜270°であることを特徴とする超
捩れネマチック(STN)液晶表示素子。
Invention 10 A super-twisted nematic (STN) liquid crystal display device using the liquid crystal composition according to any one of Inventions 1 to 8, having a twist angle of 220 ° to 270 °.

【0031】[0031]

【発明の実施の形態】以下に本発明の一例について説明
する。
DESCRIPTION OF THE PREFERRED EMBODIMENTS An example of the present invention will be described below.

【0032】発明1において、第一成分として一般式
(I)から選ばれる化合物を1種もしくは2種以上を含有
するが、1種もしくは2種が好ましい。また、式中R1は炭
素原子数1〜16のアルキル基またはアルコキシル基、炭
素原子数2〜16のアルケニル基、炭素原子数3〜16のアル
ケニルオキシ基、または炭素原子数1〜10のアルコキシ
ル基で置換された炭素原子数1〜12のアルキル基を表す
が、炭素原子数1〜16のアルキル基、炭素原子数2〜16の
アルケニル基が好ましく、炭素原子数1〜8のアルキル
基、炭素原子数2〜8のアルケニル基がより好ましく、1
〜5のアルキル基もしくはアルケニル基としてRCH2=CH2-
(CH2)o(R=H、CH3-、CH3CH2CH2-、o=0、2)が特に好ま
しい。さらに、第二成分として一般式(II)、(III)から
選ばれる化合物を1種もしくは2種以上を含有するが、3
種以上が好ましく、3種〜20種がさらに好ましく、5種〜
15種が特に好ましく、その中に一般式(II)の化合物を少
なくとも2種以上含むことがより好ましい。この液晶組
成物はネマチック相上限温度が75℃以上であることを特
徴とするが、80℃以上が好ましく、85℃以上が特に好ま
しい。また、Δnは0.07〜0.18の範囲であることを特徴
とするが、0.08〜0.17が好ましい。R2、R3、R4はそれぞ
れ独立的にフッ素置換されていても良い炭素原子数1〜1
6のアルキル基またはアルコキシル基、炭素原子数2〜16
のアルケニル基、炭素原子数3〜16のアルケニルオキシ
基、または炭素原子数1〜10のアルコキシル基で置換さ
れた炭素原子数1〜12のアルキル基を表すが、炭素原子
数1〜16のアルキル基、炭素原子数2〜16のアルケニル基
が好ましく、炭素原子数1〜8のアルキル基、炭素原子数
2〜8のアルケニル基がより好ましく、1〜5のアルキル基
もしくはアルケニル基としてRCH2=CH2-(CH2)o(R=H、CH
3-、CH3CH2CH2-、o=0、2)が特に好ましい。環A、環B、
環C、環D及び環Eはそれぞれ独立的にフッ素原子により
置換されていてもよい1,4-フェニレン基、2-メチル-1,4
-フェニレン基、3-メチル-1,4-フェニレン基、2,6-ナフ
チレン基、2,7-フェナントリレン基、2,7-フルオレン
基、トランス-1,4-シクロヘキシレン基、2,6-テトラリ
ン基、2,6-デカリン基、トランス-1,3ジオキサン-2,5-
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-ジイル基またはピリダジン-2,5-
ジイル基を表すが、1,4-フェニレン基、トランス-1,4-
シクロヘキシレン基が好ましく、環A、B、D、Eにおいて
はトランス-1,4-シクロヘキシレン基がより好ましく、
環Cにおいては1,4-フェニレン基より好ましい。l、mは
それぞれ独立的に0、1もしくは2を表すが、0もしくは1
が好ましい。Z1、Z2、Z3、Z4はそれぞれ独立的に単結
合、-CH2CH2-、-(CH2)4-、-OCH2-、-CH2O-または-C≡C-表
すが、Z1、Z2においては単結合もしくは-CH2CH2-が好ま
しく、単結合がより好ましい。Z3、Z4においては単結合
もしくは-C≡C-が好ましく、単結合がより好ましい。X2
はシアノ基、フッ素原子、塩素原子、トリフルオロメト
キシ基、トリフルオロメチル基、ジフルオロメトキシ
基、水素原子、3,3,3-トリフルオロエトキシ基、R'また
は-OR'を表し、R'は炭素原子数1〜12の直鎖状アルキル
基または、2〜12の直鎖状アルケニル基を表すが、シア
ノ基、フッ素原子、トリフルオロメトキシ基、ジフルオ
ロメトキシ基が好ましく、フッ素原子、トリフルオロメ
トキシ基、ジフルオロメトキシ基がより好ましく、フッ
素原子が特に好ましい。X1、X3は水素原子、フッ素原子
または塩素原子を表すが、水素原子、フッ素原子が好ま
しく、フッ素原子が特に好ましい。
In the invention 1, the first component contains one or more compounds selected from the general formula (I), and one or two compounds are preferable. In the formula, R1 is an alkyl group or alkoxyl group having 1 to 16 carbon atoms, an alkenyl group having 2 to 16 carbon atoms, an alkenyloxy group having 3 to 16 carbon atoms, or an alkoxyl group having 1 to 10 carbon atoms. Represents an alkyl group having 1 to 12 carbon atoms substituted with, an alkyl group having 1 to 16 carbon atoms, an alkenyl group having 2 to 16 carbon atoms is preferable, an alkyl group having 1 to 8 carbon atoms, An alkenyl group having 2 to 8 atoms is more preferable, and 1
RCH2 = CH2- as an alkyl group or alkenyl group of
(CH2) o (R = H, CH3-, CH3CH2CH2-, o = 0, 2) is particularly preferred. Further, as a second component, contains one or more compounds selected from the general formulas (II) and (III),
Or more are preferable, 3 to 20 are more preferable, and 5 to
15 types are particularly preferable, and it is more preferable that at least 2 types of the compound of the general formula (II) are contained therein. This liquid crystal composition is characterized in that the maximum temperature of the nematic phase is 75 ° C. or higher, preferably 80 ° C. or higher, particularly preferably 85 ° C. or higher. Also, Δn is in the range of 0.07 to 0.18, preferably 0.08 to 0.17. R 2 , R 3 , and R 4 each independently may have 1 to 1 carbon atoms which may be substituted by fluorine.
6 alkyl or alkoxyl groups, 2 to 16 carbon atoms
Represents an alkenyl group, an alkenyloxy group having 3 to 16 carbon atoms, or an alkyl group having 1 to 12 carbon atoms substituted with an alkoxyl group having 1 to 10 carbon atoms, but an alkyl group having 1 to 16 carbon atoms. Group, an alkenyl group having 2 to 16 carbon atoms is preferable, an alkyl group having 1 to 8 carbon atoms,
2 to 8 alkenyl groups are more preferable, and RCH 2も し く は CH 2- (CH 2 ) o (R = H, CH
3- , CH 3 CH 2 CH 2- , o = 0, 2) are particularly preferred. Ring A, Ring B,
Ring C, ring D and ring E are each independently a 1,4-phenylene group optionally substituted by a fluorine atom, 2-methyl-1,4
-Phenylene group, 3-methyl-1,4-phenylene group, 2,6-naphthylene group, 2,7-phenanthrylene group, 2,7-fluorene group, trans-1,4-cyclohexylene group, 2,6- Tetralin group, 2,6-decalin group, trans-1,3 dioxane-2,5-
Diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, pyrazine-2,5-diyl or pyridazine-2,5-
Represents a diyl group, but a 1,4-phenylene group, trans-1,4-
A cyclohexylene group is preferable, and in rings A, B, D, and E, a trans-1,4-cyclohexylene group is more preferable,
In ring C, a 1,4-phenylene group is more preferable. l and m each independently represent 0, 1 or 2, but 0 or 1
Is preferred. Z 1, Z 2, Z 3 , Z 4 are each independently a single bond, -CH 2 CH 2 -, - (CH 2) 4 -, - OCH 2 -, - CH 2 O- or -C≡C- As shown, Z 1 and Z 2 are preferably a single bond or —CH 2 CH 2 —, and more preferably a single bond. In Z 3 and Z 4 , a single bond or —C≡C— is preferable, and a single bond is more preferable. X 2
Represents a cyano group, a fluorine atom, a chlorine atom, a trifluoromethoxy group, a trifluoromethyl group, a difluoromethoxy group, a hydrogen atom, a 3,3,3-trifluoroethoxy group, R 'or -OR', and R 'is Represents a linear alkyl group having 1 to 12 carbon atoms or a linear alkenyl group having 2 to 12 carbon atoms, preferably a cyano group, a fluorine atom, a trifluoromethoxy group, a difluoromethoxy group, and a fluorine atom, trifluoromethoxy And a difluoromethoxy group are more preferred, and a fluorine atom is particularly preferred. X 1 and X 3 represent a hydrogen atom, a fluorine atom or a chlorine atom, preferably a hydrogen atom or a fluorine atom, particularly preferably a fluorine atom.

【0033】発明2において、各化合物の含有率は5〜40
%重量であるが、5〜25重量%が好ましく、5〜15重量%が
特に好ましい。
In the invention 2, the content of each compound is from 5 to 40.
%, Preferably from 5 to 25% by weight, particularly preferably from 5 to 15% by weight.

【0034】発明4において、一般式(I)の化合物を1
種もしくは2種以上を含有しその含有率が5〜40重量%の
範囲で、なおかつ一般式(II-a)の化合物を1種もしくは2
種以上を含有しその含有率が5〜40重量%の範囲である
が、一般式(I)の化合物を1種もしくは2種含有しその
含有率が5〜15重量%の範囲であることが好ましく、一般
式(II-a)の化合物を2種以上含有しその含有率が5〜15重
量%の範囲であることが好ましい。
In the invention 4, the compound of the general formula (I) is
One or two or more of the compounds of the general formula (II-a)
The compound contains at least one species and the content is in the range of 5 to 40% by weight, but the compound of the general formula (I) may contain one or two kinds and the content is in the range of 5 to 15% by weight. Preferably, two or more compounds of the general formula (II-a) are contained and the content is preferably in the range of 5 to 15% by weight.

【0035】発明6において、一般式(I)の化合物を1
種もしくは2種以上を含有し、その含有率が5〜40重量%
の範囲で、なおかつ第二成分として一般式(III-a)の化
合物を1種もしくは2種以上を含有し、その含有率が5〜4
0重量%の範囲であるが、一般式(I)の化合物を1種もし
くは2種含有しその含有率が5〜15重量%の範囲であるこ
とが好ましく、一般式(III-a)の化合物を1種〜10種含有
しその含有率が5〜15重量%の範囲であることが好まし
い。
In the invention 6, the compound of the general formula (I) is
Contains at least two species, the content of which is 5-40% by weight
Contains, as a second component, one or more compounds of the general formula (III-a), the content of which is 5 to 4
Although it is in the range of 0% by weight, it is preferable that one or two compounds of the general formula (I) are contained and the content thereof is in the range of 5 to 15% by weight, and the compound of the general formula (III-a) Is preferably contained in an amount of 5 to 15% by weight.

【0036】発明7において、一般式(I)の化合物を1
種もしくは2種以上を含有し、その含有率が5〜40重量%
の範囲で、なおかつ一般式(II-b)から選ばれる1種もし
くは2種以上の化合物を含有し、その含有率が5〜40重量
%の範囲で、さらに一般式(II-c)から選ばれる1種もしく
は2種以上の化合物を含有しその含有率が5〜40重量%の
範囲であるが、一般式(II-b)、(II-c)の化合物を5種〜1
5種含有しその含有率が5〜15重量%の範囲であることが
好ましくい。式中R8、R9、R10、R11はそれぞれ独立的に
炭素原子数1〜8のアルキル基または炭素原子数2〜8のア
ルケニル基を表すが、1〜5のアルキル基もしくはアルケ
ニル基としてRCH2=CH2-(CH2)o(R=H、CH3-、CH3CH2CH
2-、o=0、2)が特に好ましい。
In the invention 7, the compound of the general formula (I) is
Contains at least two species, the content of which is 5-40% by weight
Contains one or more compounds selected from the general formula (II-b), and the content is 5 to 40% by weight.
%, Further contains one or more compounds selected from the general formula (II-c), the content of which is in the range of 5 to 40% by weight, the general formula (II-b), 5 to 1 compounds of (II-c)
It is preferable that five types be contained and the content be in the range of 5 to 15% by weight. In the formula, R 8 , R 9 , R 10 , and R 11 each independently represent an alkyl group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms, and an alkyl group or alkenyl group having 1 to 5 carbon atoms. RCH 2 = CH 2- (CH 2 ) o (R = H, CH 3- , CH 3 CH 2 CH
2- , o = 0, 2) are particularly preferred.

【0037】発明8において、発明1記載の一般式(III)
もしくは一般式(III-a)として、一般式(III-b)から選ば
れる1種もしくは2種以上の化合物を含有しその含有率が
5〜40重量%の範囲であるが、一般式(III-b)の化合物を1
〜15種含有しその含有率が5〜15重量%の範囲であること
が好ましく1〜10種がより好ましい。式中R12は炭素原子
数1〜8のアルキル基または炭素原子数2〜8のアルケニル
基を表すが、1〜5のアルキル基もしくはアルケニル基と
してRCH2=CH2-(CH2)o(R=H、CH3-、CH3CH2CH2-、o=0、
2)が特に好ましい。
In the invention 8, the general formula (III) described in the invention 1
Or, as the general formula (III-a), contains one or more compounds selected from the general formula (III-b) and the content thereof is
In the range of 5 to 40% by weight, the compound of the general formula (III-b)
Preferably, the content is in the range of 5 to 15% by weight, more preferably 1 to 10 types. In the formula, R 12 represents an alkyl group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms, and RCH 2 CHCH 2 — (CH 2 ) o (1 to 5 alkyl groups or alkenyl groups) R = H, CH 3- , CH 3 CH 2 CH 2- , o = 0,
2) is particularly preferred.

【0038】上記ネマチック液晶組成物はTN-LCDやSTN-
LCDに有用であるがSTN-LCDに特に有用である。また、透
過型あるいは反射型の液晶表示素子に用いることができ
る。本発明の液晶組成物は、上記一般式(I)〜(VII
I)で表される化合物以外に、通常のネマチック液晶、
スメクチック液晶、コレステリック液晶などを含有して
いてもよい。
The above nematic liquid crystal composition is TN-LCD or STN-
Useful for LCDs, but especially useful for STN-LCDs. Further, it can be used for a transmissive or reflective liquid crystal display device. The liquid crystal composition of the present invention has the general formulas (I) to (VII)
In addition to the compounds represented by I), ordinary nematic liquid crystals,
It may contain a smectic liquid crystal, a cholesteric liquid crystal, or the like.

【0039】[0039]

【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。また、以下の実施例及び比較例の組成物における
「%」は『重量%』を意味する。
EXAMPLES The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples. Further, “%” in the compositions of the following Examples and Comparative Examples means “% by weight”.

【0040】実施例中、測定した特性は以下の通りであ
る。
The characteristics measured in the examples are as follows.

【0041】 TN-I :ネマチック相−等方性液体相転移温度(℃) T→N :固体相又はスメクチック相−ネマチック相転移温度(℃) Vth :セル厚6μmのTN-LCDを構成した時のしきい値電圧(V) Δε :誘電異方性 Δn :複屈折率 η :20℃での粘度(mPaキs) Ir :240°ツイストのSTN-LCDに液晶組成物を真空注入し、80℃、 100時間加熱後の電流値(μA/cm2) CR :240°ツイストのSTN-LCDに液晶組成物を真空注入し、1/200 デューティ、1/16バイアスの駆動波形で駆動したときのコントラスト。T NI : Nematic phase-isotropic liquid phase transition temperature (℃) T → N : Solid phase or smectic phase-nematic phase transition temperature (° C) Vth: Threshold voltage (V) when a TN-LCD having a cell thickness of 6 μm is formed Δε: Dielectric anisotropy Δn: Birefringence η: 20 ° C Viscosity (mPa Kis) Ir: 240 ° twist STN-LCD, liquid crystal composition is vacuum-injected, current value after heating at 80 ° C for 100 hours (μA / cm 2 ) CR: 240 ° twist STN- Contrast when liquid crystal composition is vacuum-injected into LCD and driven with 1/200 duty, 1/16 bias drive waveform.

【0042】STN-LCD表示素子の作成は以下のように行
った。ネマチック液晶組成物にカイラル物質「S-811」
(メルク社製)を添加して混合液晶を調製し、対向する
平面透明電極上に「サンエバー610」(日産化学社製)
の有機膜をラビングして配向膜を形成したツイスト角24
0度のSTN-LCD表示用セルに注入した。なお、カイラル物
質はカイラル物質の添加による混合液晶の固有らせんピ
ッチPと表示用セルのセル厚dが、Δn・d=0.85、d/P=0.5
0となるように添加した。
The production of the STN-LCD display element was performed as follows. Chiral substance "S-811" in nematic liquid crystal composition
(Merck) was added to prepare a mixed liquid crystal, and “Sanever 610” (manufactured by Nissan Chemical Industries) was placed on the opposing flat transparent electrode.
Twist angle of 24 after rubbing the organic film
It was injected into a 0 degree STN-LCD display cell. Note that the chiral substance is such that the specific helical pitch P of the mixed liquid crystal due to the addition of the chiral substance and the cell thickness d of the display cell are Δn · d = 0.85, d / P = 0.5
It was added so as to be 0.

【0043】化合物記載に下記の略号を使用する。The following abbreviations are used in describing the compounds.

【0044】 末端のn(数字) CnH2n+1- C トランス-1,4-シクロヘキシレン基 C/ 1,4-シクロヘキセンジイル基 P 1,4フェニレン基 Pm ピリミジン-2,5-ジイル基 E -COO- e -OCO- A -CH2CH2- t -C≡C- CN -C≡N On -OCnH2n+1 F -F f 末端基のオルト位に結合したF原子 ndm- CnH2n+1-C=C-(CH2)m-1- -O(dm)n -O(CH2)m-2-C=C-CnH2n+1 (実施例1、比較例1)ネマチック液晶組成物No.1Terminal n (number) C n H 2n + 1 -C trans-1,4-cyclohexylene group C / 1,4-cyclohexenediyl group P 1,4 phenylene group Pm pyrimidine-2,5-diyl group E -COO- e -OCO- A -CH 2 CH 2 -t -C≡C- CN -C≡N On -OC n H 2n + 1 F -F f F atom bound to the ortho position of the terminal group ndm- C n H 2n + 1 -C = C- (CH 2 ) m-1 --O (dm) n -O (CH2) m-2-C = C-CnH2n + 1 (Example 1, Comparative Example 1) Nematic liquid crystal composition No.1

【0045】[0045]

【化15】 Embedded image

【0046】を調製し、この組成物の諸特性を測定した
結果を比較例1と共に表1に示す。
Table 1 shows the results of measuring various properties of this composition together with Comparative Example 1.

【0047】[0047]

【表1】 表1に示すように、実施例1の液晶組成物は、比較例1の
組成物に比べ電流値を大幅に抑制しているうえにコント
ラストも改善している。ここで作製したTN-LCDを用いて
電気光学特性の-10℃〜60℃での温度依存性を測定した
ところ、1.4mV/℃と優れた表示特性を示す液晶表示装置
を作成することができた。
[Table 1] As shown in Table 1, the liquid crystal composition of Example 1 significantly suppressed the current value and improved the contrast as compared with the composition of Comparative Example 1. Using the TN-LCD fabricated here, the temperature dependence of the electro-optical characteristics at -10 ° C to 60 ° C was measured, and a liquid crystal display device with excellent display characteristics of 1.4 mV / ° C was produced. Was.

【0048】(実施例2)ネマチック液晶組成物No.2を
調製し(実施例2)諸特性を測定した、また比較の組成
物として本発明外の組成物組成物の組成及び特性データ
(比較例2)と共に表2に示した。
Example 2 A nematic liquid crystal composition No. 2 was prepared (Example 2), and its various characteristics were measured. As a comparative composition, the composition and characteristic data of a composition other than the present invention (comparative) The results are shown in Table 2 together with Example 2).

【0049】[0049]

【表2】 [Table 2]

【0050】表2に示すように、実施例2の液晶組成物も
また、比較例2の組成物に比べ電流値を大幅に抑制し、
駆動電圧も改善している。
As shown in Table 2, the liquid crystal composition of Example 2 also significantly suppressed the current value as compared with the composition of Comparative Example 2,
The drive voltage has also improved.

【0051】ここで作製したTN-LCDを用いて電気光学特
性の-10℃〜60℃での温度依存性を測定したところ、1.3
mV/℃と優れた表示特性を示す液晶表示装置を作成する
ことができた。 (実施例3)ネマチック液晶組成物No.3〜5を調製し組成
及び特性データを表3に示した。
The temperature dependence of the electro-optical characteristics at -10 ° C. to 60 ° C. was measured using the TN-LCD fabricated here.
A liquid crystal display device exhibiting excellent display characteristics of mV / ° C. was produced. Example 3 Nematic liquid crystal compositions Nos. 3 to 5 were prepared, and the composition and characteristic data are shown in Table 3.

【0052】[0052]

【表3】 [Table 3]

【0053】これらの組成物からもまた、優れた温度依
存性および低い電流値の液晶表示素子を作成することが
できた。
Also from these compositions, a liquid crystal display device having excellent temperature dependency and low current value could be produced.

【0054】[0054]

【発明の効果】本発明の液晶材料の組み合わせによっ
て、電流値が抑制された誘電率異方性の高い液晶組成物
が得られた。また、この組成物を液晶表示素子として用
いた場合、閾値電圧が低く、その温度特性は優れたもの
であった。この液晶ディスプレイはSTNおよびTN-LCDと
して非常に実用的である。
By the combination of the liquid crystal materials of the present invention, a liquid crystal composition having a suppressed current value and a high dielectric anisotropy was obtained. When this composition was used for a liquid crystal display device, the threshold voltage was low and the temperature characteristics were excellent. This liquid crystal display is very practical as STN and TN-LCD.

───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 FI テーマコート゛(参考) G02F 1/13 500 G02F 1/13 500 Fターム(参考) 4H027 BA01 BB04 BD23 BE05 CB01 CE04 CL01 CM01 CM04 CN01 CN04 CQ02 CQ04 CT01 CT02 CT03 CT04 CU04 CW02 DE04 DP01 ──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. 7 Identification code FI Theme coat ゛ (Reference) G02F 1/13 500 G02F 1/13 500 F term (Reference) 4H027 BA01 BB04 BD23 BE05 CB01 CE04 CL01 CM01 CM04 CN01 CN04 CQ02 CQ04 CT01 CT02 CT03 CT04 CU04 CW02 DE04 DP01

Claims (10)

【特許請求の範囲】[Claims] 【請求項1】 第一成分として、一般式(I) 【化1】 (式中、R1は、炭素原子数1〜16のアルキル基またはア
ルコキシル基、炭素原子数2〜16のアルケニル基、炭素
原子数3〜16のアルケニルオキシ基、または炭素原子数1
〜10のアルコキシル基で置換された炭素原子数1〜12の
アルキル基を表す。)から選ばれる化合物を1種もしく
は2種以上を含有し、第二成分として、一般式(II)、(II
I) 【化2】 (式中、R2、R3、R4は、それぞれ独立的に、フッ素置換
されていても良い炭素原子数1〜16のアルキル基または
アルコキシル基、炭素原子数2〜16のアルケニル基、炭
素原子数3〜16のアルケニルオキシ基、または炭素原子
数1〜10のアルコキシル基で置換された炭素原子数1〜12
のアルキル基を表し、環A、環B、環C、環D及び環Eは、
それぞれ独立的に、フッ素原子により置換されていても
よい1,4-フェニレン基、2-メチル-1,4-フェニレン基、3
-メチル-1,4-フェニレン基、2,6-ナフチレン基、2,7-フ
ェナントリレン基、2,7-フルオレン基、トランス-1,4-
シクロヘキシレン基、2,6-テトラリン基、2,6-デカリン
基、トランス-1,3ジオキサン-2,5-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-ジイル基またはピリダジン-2,5-ジイル基を表し、l、
mは、それぞれ独立的に、0、1もしくは2を表し、Z1
Z2、Z3、Z4は、それぞれ独立的に、単結合、-CH2CH2-、-
(CH2)4-、-OCH2-、-CH2O-または-C≡C-表し、X2はシアノ
基、フッ素原子、塩素原子、トリフルオロメトキシ基、
トリフルオロメチル基、ジフルオロメトキシ基、水素原
子、3,3,3-トリフルオロエトキシ基、R'または-OR'を表
し、R'は炭素原子数1〜12の直鎖状アルキル基または炭
素原子数2〜12の直鎖状アルケニル基を表し、X1、X
3は、それぞれ独立的に、水素原子、フッ素原子または
塩素原子を表す。ただし、環Dがピリミジン-2,5-ジイル
基、m=0及びZ4が単結合である場合、X 1、X3が同時にフ
ッ素原子ではなく、X2がR'または-OR'を表す場合、X1
X3は同時に水素原子ではない。)から選ばれる化合物を
1種もしくは2種以上を含有し、なおかつネマチック相上
限温度が75℃以上であり、屈折率の異方性(Δn)が0.0
7〜0.18の範囲であることを特徴とする液晶組成物。
1. A compound represented by the following general formula (I):(Where R1Is an alkyl group having 1 to 16 carbon atoms or
Lucoxyl group, alkenyl group having 2 to 16 carbon atoms, carbon
An alkenyloxy group having 3 to 16 atoms, or 1 carbon atom
1 to 12 carbon atoms substituted with an alkoxyl group
Represents an alkyl group. One or more compounds selected from
Contains two or more kinds, and as the second component, the general formulas (II) and (II)
I)(Where RTwo, RThree, RFourAre each independently fluorine-substituted
An alkyl group having 1 to 16 carbon atoms which may be
Alkoxyl group, alkenyl group having 2 to 16 carbon atoms, carbon
An alkenyloxy group having 3 to 16 atoms, or carbon atom
1 to 12 carbon atoms substituted with an alkoxyl group of 1 to 10
A ring A, ring B, ring C, ring D and ring E,
Even if each is independently substituted by a fluorine atom
Good 1,4-phenylene group, 2-methyl-1,4-phenylene group, 3
-Methyl-1,4-phenylene group, 2,6-naphthylene group, 2,7-phenyl
Enanthrylene group, 2,7-fluorene group, trans-1,4-
Cyclohexylene group, 2,6-tetralin group, 2,6-decalin
Group, trans-1,3 dioxane-2,5-diyl group, pyridine-
2,5-diyl group, pyrimidine-2,5-diyl group, pyrazine-2,
Represents a 5-diyl group or a pyridazine-2,5-diyl group, l,
m independently represents 0, 1 or 2; Z1,
ZTwo, ZThree, ZFourIs independently a single bond, -CHTwoCHTwo-,-
(CHTwo)Four-, -OCHTwo-, -CHTwoO- or -C≡C- stands for XTwoIs cyano
Group, fluorine atom, chlorine atom, trifluoromethoxy group,
Trifluoromethyl group, difluoromethoxy group, hydrogen atom
, A 3,3,3-trifluoroethoxy group, R 'or -OR'
R ′ is a linear alkyl group having 1 to 12 carbon atoms or carbon
Represents a linear alkenyl group having 2 to 12 elementary atoms, X1, X
ThreeIs independently a hydrogen atom, a fluorine atom or
Represents a chlorine atom. Provided that ring D is pyrimidine-2,5-diyl
Group, m = 0 and ZFourIs a single bond, X 1, XThreeAt the same time
X, not nitrogen atomTwoRepresents R 'or -OR', X1,
XThreeAre not simultaneously hydrogen atoms. )
Contains 1 or 2 or more types, and on the nematic phase
The limiting temperature is 75 ° C or higher and the refractive index anisotropy (Δn) is 0.0
A liquid crystal composition characterized by being in the range of 7 to 0.18.
【請求項2】 第一成分として、一般式(I)の化合物を1
種もしくは2種以上を含有し、その含有率が5〜40重量%
の範囲で、さらに第二成分として、一般式(II)、一般式
(III)の化合物の中から選んだ1種もしくは2種以上を含
有し、選んだ化合物の含有率がそれぞれ5〜40重量%の範
囲であることを特徴とする請求項1記載の液晶組成物。
2. A compound of the general formula (I) as a first component
Contains at least two species, the content of which is 5-40% by weight
In the range, further as a second component, a general formula (II), a general formula
The liquid crystal composition according to claim 1, wherein the liquid crystal composition contains one or more kinds selected from the compounds of (III), and the content of each of the selected compounds is in the range of 5 to 40% by weight. .
【請求項3】 一般式(II)の化合物として、環Aおよび
環Bがトランス-1,4-シクロヘキシレン基であり、Z1、Z2
が単結合の一般式(II-a) 【化3】 (式中、R5、R6は、R2、R3と同じ意味を表し、環Fは、
1,4-フェニレン基またはトランス-1,4-シクロヘキシレ
ン基を表し、nは、0もしくは1を表す。)から選ばれる1
種もしくは2種以上の化合物を含有することを特徴とす
る請求項1又は2記載の液晶組成物。
3. The compound of the general formula (II) wherein Ring A and Ring B are trans-1,4-cyclohexylene groups, Z 1 , Z 2
Is a single bond of the general formula (II-a) (Wherein, R 5 and R 6 represent the same meaning as R 2 and R 3, and ring F is
Represents a 1,4-phenylene group or a trans-1,4-cyclohexylene group, and n represents 0 or 1. 1) selected from
3. The liquid crystal composition according to claim 1, wherein the liquid crystal composition contains one or more compounds.
【請求項4】 第一成分として、一般式(I)の化合物
を1種もしくは2種以上を含有し、その含有率が5〜40重
量%の範囲で、なおかつ第二成分として、一般式(II-a)
の化合物を1種もしくは2種以上を含有し、その含有率が
5〜40重量%の範囲であることを特徴とする請求項3記載
の液晶組成物。
4. The composition according to claim 1, wherein the first component comprises one or more compounds of the general formula (I) in a content of 5 to 40% by weight, and the second component comprises a compound of the general formula (I) II-a)
Contains one or more compounds, and the content is
4. The liquid crystal composition according to claim 3, wherein the content is in the range of 5 to 40% by weight.
【請求項5】 一般式(III)の化合物として、環Dがトラ
ンス-1,4-シクロヘキシレン基であり、Z3、Z4が単結合
であり、m=1の一般式(III-a) 【化4】 (式中、R7は、炭素原子数1〜8のアルキル基または炭素
原子数2〜8のアルケニル基を表し、環Gは、1,4-フェニ
レン基またはトランス-1,4-シクロヘキシレン基を表
し、X5は、シアノ基、フッ素原子、トリフルオロメトキ
シ基、ジフルオロメトキシ基を表し、X4、X6は、それぞ
れ独立的に、水素原子またはフッ素原子を表す。)から
選ばれる1種もしくは2種以上の化合物を含有することを
特徴とする請求項1又は2記載の液晶組成物。
5. A compound of the general formula (III-a) wherein ring D is a trans-1,4-cyclohexylene group, Z 3 and Z 4 are single bonds, and m = 1. ) (Wherein, R 7 represents an alkyl group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms, and ring G is a 1,4-phenylene group or a trans-1,4-cyclohexylene group X 5 represents a cyano group, a fluorine atom, a trifluoromethoxy group, or a difluoromethoxy group, and X 4 and X 6 each independently represent a hydrogen atom or a fluorine atom.) 3. The liquid crystal composition according to claim 1, further comprising two or more compounds.
【請求項6】 第一成分として、一般式(I)の化合物
を1種もしくは2種以上を含有し、その含有率が5〜40重
量%の範囲で、なおかつ一般式(III-a)の化合物を1種も
しくは2種以上を含有し、その含有率が5〜40重量%の範
囲であることを特徴とする請求項5記載の液晶組成物。
6. A compound comprising one or more compounds of the general formula (I) as a first component, the content of which is in the range of 5 to 40% by weight and the compound of the general formula (III-a) 6. The liquid crystal composition according to claim 5, comprising one or more compounds, and the content is in the range of 5 to 40% by weight.
【請求項7】 一般式(I)の化合物を1種もしくは2種
以上を含有し、その含有率が5〜40重量%の範囲で、なお
かつ一般式(II-b) 【化5】 (式中、R8、R9は、それぞれ独立的に、炭素原子数1〜8
のアルキル基または炭素原子数2〜8のアルケニル基を表
す。)から選ばれる1種もしくは2種以上の化合物を含有
し、その含有率が5〜40重量%の範囲で、さらに一般式(I
I-c) 【化6】 (式中、R10、R11は、それぞれ独立的に、炭素原子数1
〜8のアルキル基または炭素原子数2〜8のアルケニル基
を表す。)から選ばれる1種もしくは2種以上の化合物を
含有し、その含有率が5〜40重量%の範囲であることを特
徴とする請求項1〜6記載の液晶組成物。
7. A compound containing one or more compounds of the general formula (I) in a content of from 5 to 40% by weight and a compound of the general formula (II-b) (Wherein, R 8 and R 9 each independently represent 1 to 8 carbon atoms.
Represents an alkyl group or an alkenyl group having 2 to 8 carbon atoms. ) Containing one or two or more compounds selected from the group consisting of a compound represented by the general formula (I)
Ic) (Wherein, R 10 and R 11 each independently represent 1 carbon atom
Represents an alkyl group having up to 8 or an alkenyl group having 2 to 8 carbon atoms. 7. The liquid crystal composition according to claim 1, comprising one or more compounds selected from the group consisting of (1) and (2), and the content thereof is in the range of 5 to 40% by weight.
【請求項8】 一般式(III)もしくは(III-a)として、一
般式(III-b) 【化7】 (式中、R12は、炭素原子数1〜16のアルキル基または炭
素原子数2〜8のアルケニル基を表す。)から選ばれる1
種もしくは2種以上の化合物を含有し、その含有率が5〜
40重量%の範囲であることを特徴とする請求項1〜7記載
の液晶組成物。
8. A compound of the general formula (III-b) represented by the general formula (III) or (III-a): (In the formula, R 12 represents an alkyl group having 1 to 16 carbon atoms or an alkenyl group having 2 to 8 carbon atoms.)
Contains two or more compounds, the content of which is 5 to
8. The liquid crystal composition according to claim 1, wherein the content is in a range of 40% by weight.
【請求項9】 請求項1〜8記載の液晶組成物を用いた液
晶表示素子。
9. A liquid crystal display device using the liquid crystal composition according to claim 1.
【請求項10】 請求項1〜8記載の液晶組成物を用い
た、ねじれ角が220°〜270°であることを特徴とする超
捩れネマチック(STN)液晶表示素子。
10. A super twisted nematic (STN) liquid crystal display device using the liquid crystal composition according to claim 1 and having a twist angle of 220 ° to 270 °.
JP15371799A 1999-06-01 1999-06-01 Liquid crystal composition and liquid crystal display element Expired - Fee Related JP4505879B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP15371799A JP4505879B2 (en) 1999-06-01 1999-06-01 Liquid crystal composition and liquid crystal display element

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP15371799A JP4505879B2 (en) 1999-06-01 1999-06-01 Liquid crystal composition and liquid crystal display element

Publications (2)

Publication Number Publication Date
JP2000336364A true JP2000336364A (en) 2000-12-05
JP4505879B2 JP4505879B2 (en) 2010-07-21

Family

ID=15568573

Family Applications (1)

Application Number Title Priority Date Filing Date
JP15371799A Expired - Fee Related JP4505879B2 (en) 1999-06-01 1999-06-01 Liquid crystal composition and liquid crystal display element

Country Status (1)

Country Link
JP (1) JP4505879B2 (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000336365A (en) * 1999-06-01 2000-12-05 Dainippon Ink & Chem Inc Liquid crystal composition and liquid crystal display device
JP2002249779A (en) * 2001-02-27 2002-09-06 Dainippon Ink & Chem Inc Liquid crystal composition and liquid crystal display element
KR20030003770A (en) * 2001-04-03 2003-01-14 주식회사 현대 디스플레이 테크놀로지 Fringe field switching liquid crystal display
JP2003073671A (en) * 2001-08-31 2003-03-12 Dainippon Ink & Chem Inc Liquid crystal composition and liquid crystal display element
US6620467B2 (en) 2000-07-25 2003-09-16 Dainippon Ink And Chemicals, Inc. Liquid crystal display
JP2005187604A (en) * 2003-12-25 2005-07-14 Dainippon Ink & Chem Inc Liquid crystal composition and liquid crystal display element
JP5652202B2 (en) * 2008-04-09 2015-01-14 Jnc株式会社 Tricyclic liquid crystalline compound having lateral fluorine, liquid crystal composition, and liquid crystal display device
US8968840B2 (en) 2004-07-02 2015-03-03 Merck Patent Gmbh Liquid-crystalline medium

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0338572A (en) * 1989-07-05 1991-02-19 Seiko Epson Corp Pyrimidine derivative
JPH06321901A (en) * 1993-04-03 1994-11-22 Merck Patent Gmbh Cyanophenylpyri(mi)dine derivative and liquid crystal medium
DE4327749A1 (en) * 1993-08-18 1995-02-23 Merck Patent Gmbh Process for the preparation of 2-fluoroarylonitrile derivatives
JPH09323944A (en) * 1996-06-04 1997-12-16 Chisso Corp Liquid crystal compound containing unsaturated bond in bond group, liquid crystal composition and liquid crystal display element
JPH1077475A (en) * 1996-08-30 1998-03-24 Dainippon Ink & Chem Inc Nematic liquid crystal composition and liquid crystal display made by using it
JP2000336365A (en) * 1999-06-01 2000-12-05 Dainippon Ink & Chem Inc Liquid crystal composition and liquid crystal display device
JP2001500894A (en) * 1996-09-27 2001-01-23 チッソ株式会社 Compound having alkadienyl group as side chain, and liquid crystal composition using the same

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0338572A (en) * 1989-07-05 1991-02-19 Seiko Epson Corp Pyrimidine derivative
JPH06321901A (en) * 1993-04-03 1994-11-22 Merck Patent Gmbh Cyanophenylpyri(mi)dine derivative and liquid crystal medium
DE4327749A1 (en) * 1993-08-18 1995-02-23 Merck Patent Gmbh Process for the preparation of 2-fluoroarylonitrile derivatives
JPH09323944A (en) * 1996-06-04 1997-12-16 Chisso Corp Liquid crystal compound containing unsaturated bond in bond group, liquid crystal composition and liquid crystal display element
JPH1077475A (en) * 1996-08-30 1998-03-24 Dainippon Ink & Chem Inc Nematic liquid crystal composition and liquid crystal display made by using it
JP2001500894A (en) * 1996-09-27 2001-01-23 チッソ株式会社 Compound having alkadienyl group as side chain, and liquid crystal composition using the same
JP2000336365A (en) * 1999-06-01 2000-12-05 Dainippon Ink & Chem Inc Liquid crystal composition and liquid crystal display device

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000336365A (en) * 1999-06-01 2000-12-05 Dainippon Ink & Chem Inc Liquid crystal composition and liquid crystal display device
JP4505880B2 (en) * 1999-06-01 2010-07-21 Dic株式会社 Liquid crystal composition and liquid crystal display element
US6620467B2 (en) 2000-07-25 2003-09-16 Dainippon Ink And Chemicals, Inc. Liquid crystal display
JP2002249779A (en) * 2001-02-27 2002-09-06 Dainippon Ink & Chem Inc Liquid crystal composition and liquid crystal display element
KR20030003770A (en) * 2001-04-03 2003-01-14 주식회사 현대 디스플레이 테크놀로지 Fringe field switching liquid crystal display
JP2003073671A (en) * 2001-08-31 2003-03-12 Dainippon Ink & Chem Inc Liquid crystal composition and liquid crystal display element
JP2005187604A (en) * 2003-12-25 2005-07-14 Dainippon Ink & Chem Inc Liquid crystal composition and liquid crystal display element
US8968840B2 (en) 2004-07-02 2015-03-03 Merck Patent Gmbh Liquid-crystalline medium
US9267078B2 (en) 2004-07-02 2016-02-23 Merck Patent Gmbh Liquid crystalline medium
US9340730B2 (en) 2004-07-02 2016-05-17 Merck Patent Gmbh Liquid crystalline medium
US9701903B2 (en) 2004-07-02 2017-07-11 Merck Patent Gmbh Liquid crystalline medium
US10144870B2 (en) 2004-07-02 2018-12-04 Merck Patent Gmbh Liquid crystalline medium
US10150917B2 (en) 2004-07-02 2018-12-11 Merck Patent Gmbh Liquid crystalline medium
US10160909B2 (en) 2004-07-02 2018-12-25 Merck Patent Gmbh Liquid crystalline medium
US10435626B2 (en) 2004-07-02 2019-10-08 Merck Patent Gmbh Liquid crystalline medium
US10533135B2 (en) 2004-07-02 2020-01-14 Merck Patent Gesellschaft Mit Beschrankter Haftung Liquid crystalline medium
US10611963B2 (en) 2004-07-02 2020-04-07 Merck Patent Gmbh Liquid crystalline medium
JP5652202B2 (en) * 2008-04-09 2015-01-14 Jnc株式会社 Tricyclic liquid crystalline compound having lateral fluorine, liquid crystal composition, and liquid crystal display device

Also Published As

Publication number Publication date
JP4505879B2 (en) 2010-07-21

Similar Documents

Publication Publication Date Title
JP3856188B2 (en) Liquid crystal composition
JP4872147B2 (en) Liquid crystal composition and liquid crystal display element
JP4505879B2 (en) Liquid crystal composition and liquid crystal display element
JP4505880B2 (en) Liquid crystal composition and liquid crystal display element
JP4984342B2 (en) Liquid crystal composition
JP4973900B2 (en) Nematic liquid crystal composition and liquid crystal display device using the same
JP4324816B2 (en) Nematic liquid crystal composition and liquid crystal display device using the same
JP4655317B2 (en) Liquid crystal composition and liquid crystal display element
JP4934899B2 (en) Liquid crystal composition and liquid crystal display element
JP4815671B2 (en) Liquid crystal composition
JP4956861B2 (en) Liquid crystal display element
JP4984105B2 (en) Liquid crystal composition and liquid crystal display element
JP4876352B2 (en) Liquid crystal composition and liquid crystal display element
JP4894099B2 (en) Nematic liquid crystal composition and liquid crystal display device using the same
JP4918734B2 (en) Liquid crystal composition and liquid crystal display element
JP4887560B2 (en) Liquid crystal composition
JP2003064367A (en) Liquid crystal display element
JP4876314B2 (en) Liquid crystal composition and liquid crystal display element
JP4595329B2 (en) Nematic liquid crystal composition and liquid crystal display device using the same
JP4243929B2 (en) Liquid crystal composition and liquid crystal display element
JP2003193052A (en) Nematic liquid crystal composition and liquid crystal display device using the same
JP4701586B2 (en) Liquid crystal composition and liquid crystal display element
JP4218082B2 (en) Nematic liquid crystal composition and liquid crystal display device using the same
JP4415240B2 (en) Liquid crystal composition and liquid crystal display element
JP2002226859A (en) Nematic liquid crystal composition and liquid crystal display device using the same

Legal Events

Date Code Title Description
RD01 Notification of change of attorney

Free format text: JAPANESE INTERMEDIATE CODE: A7421

Effective date: 20050721

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20060524

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20100105

A521 Written amendment

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20100308

TRDD Decision of grant or rejection written
A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

Effective date: 20100406

A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20100419

FPAY Renewal fee payment (event date is renewal date of database)

Free format text: PAYMENT UNTIL: 20130514

Year of fee payment: 3

R150 Certificate of patent or registration of utility model

Ref document number: 4505879

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

Free format text: JAPANESE INTERMEDIATE CODE: R150

FPAY Renewal fee payment (event date is renewal date of database)

Free format text: PAYMENT UNTIL: 20130514

Year of fee payment: 3

FPAY Renewal fee payment (event date is renewal date of database)

Free format text: PAYMENT UNTIL: 20130514

Year of fee payment: 3

FPAY Renewal fee payment (event date is renewal date of database)

Free format text: PAYMENT UNTIL: 20140514

Year of fee payment: 4

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

LAPS Cancellation because of no payment of annual fees