JP2002327175A - Liquid crystal composition and liquid crystal display device - Google Patents

Liquid crystal composition and liquid crystal display device

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Publication number
JP2002327175A
JP2002327175A JP2001132752A JP2001132752A JP2002327175A JP 2002327175 A JP2002327175 A JP 2002327175A JP 2001132752 A JP2001132752 A JP 2001132752A JP 2001132752 A JP2001132752 A JP 2001132752A JP 2002327175 A JP2002327175 A JP 2002327175A
Authority
JP
Japan
Prior art keywords
liquid crystal
general formula
cf2obb
compound represented
hbb
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
JP2001132752A
Other languages
Japanese (ja)
Other versions
JP4300714B2 (en
Inventor
Hiroaki Fujita
浩章 藤田
Yasuhiro Kubo
恭宏 久保
Katsuyuki Muraki
勝之 村城
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.)
JNC Corp
JNC Petrochemical Corp
Original Assignee
Chisso Petrochemical Corp
Chisso Corp
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 Chisso Petrochemical Corp, Chisso Corp filed Critical Chisso Petrochemical Corp
Priority to JP2001132752A priority Critical patent/JP4300714B2/en
Publication of JP2002327175A publication Critical patent/JP2002327175A/en
Application granted granted Critical
Publication of JP4300714B2 publication Critical patent/JP4300714B2/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K2019/0444Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
    • C09K2019/0466Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the linking chain being a -CF2O- chain

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  • Liquid Crystal Substances (AREA)

Abstract

PROBLEM TO BE SOLVED: To provide a liquid crystal composition having a moderate threshold voltage, high reliability and high anisotropic value Δn of refractive index and a liquid crystal display device obtained by using the composition. SOLUTION: This liquid crystal composition is provided by including the first component composed of a compound represented by general formula (1) and the second component composed of at least one kind selected from the group composed of compounds represented by general formulae (2-1) and (2-2) (wherein, R<1> denotes a 1-10C alkyl; R<2> and R<3> denote each a 1-10C alkyl, a 1-10C alkoxy, a 2-10C alkoxymethyl or a 2-10C alkenyl, independently; Z1 and Z2 denote each -C2 H4 - or single bond, independently; X1 and X2 denote each F, Cl, CF3 , OCF3 , OCF2 H, a 1-10C alkyl, a 1-10C alkoxy, a 2-10C alkoxymethyl or a 2-10C alkenyl, independently; and Y1 , Y2 , Y3 , Y4 , Y5 , Y6 , Y7 , Y8 , Y9 and Y10 denote each H or F, independently). The liquid crystal display device is formed by using the composition.

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、ネマチック液晶組
成物に関し、さらに詳しくは、アクティブマトリックス
LCD表示方式を用いた液晶表示素子に好適に使用され
る液晶組成物、およびこの液晶組成物を用いた液晶表示
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, and more particularly, to a liquid crystal composition suitably used for a liquid crystal display device using an active matrix LCD display system and a liquid crystal composition using the same. The present invention relates to a liquid crystal display device.

【0002】[0002]

【従来の技術】液晶表示素子(LCD)は、CRT(ブ
ラウン管方式ディスプレイ)に比べて、低消費電力、小
型化、軽量化が可能であるために、ツイステッドネマテ
ィック(TN)方式、スーパーツイステッドネマティッ
ク(STN)方式、薄膜トランジスター(TFT)方式
等の種々のLCDが実用化されてきた。その中で薄膜ト
ランジスター(TFT)方式等のアクティブマトリック
スLCD(AM−LCD)はカラー化、高精細化が進み
フラットパネルディスプレイとして広く普及している。
また、近年、次世代の有望な高速応答表示モードとし
て、OCB(Optically Compensated Birefringence)
方式のLCDが脚光を浴びてきている。
2. Description of the Related Art A liquid crystal display (LCD) has a lower power consumption, a smaller size, and a lighter weight than a CRT (CRT display). Various LCDs such as an STN type and a thin film transistor (TFT) type have been put to practical use. Among them, an active matrix LCD (AM-LCD) such as a thin film transistor (TFT) system has been widely used as a flat panel display with progress in color and definition.
In recent years, OCB (Optically Compensated Birefringence) has been proposed as a promising next-generation high-speed display mode.
LCDs are in the limelight.

【0003】AM−LCD用液晶組成物に求められる一
般的な特性には、(1)LCDの高コントラストを維持
するために、液晶組成物を注入したセルの電圧保持率
(V.H.R)が高いこと、(2)ネマティック液晶相
を示す温度範囲が広いこと、(3)セル厚に応じて、適
当な屈折率異方性(Δn)を取り得ること、(4)駆動
回路に応じて、適当なしきい値電圧を取り得ること、が
ある。セル厚が小さい、特に、好ましくは3μm以下の
セル厚のAM−LCDに用いられる液晶材料には、上記
(3)項のΔnの値が大きいことが要求される。
[0003] The general characteristics required of a liquid crystal composition for AM-LCD include (1) a voltage holding ratio (VHR) of a cell into which the liquid crystal composition is injected in order to maintain a high contrast of the LCD. ) Is high, (2) the temperature range showing the nematic liquid crystal phase is wide, (3) an appropriate refractive index anisotropy (Δn) can be obtained depending on the cell thickness, and (4) depending on the driving circuit. Therefore, an appropriate threshold voltage can be obtained. A liquid crystal material used for an AM-LCD having a small cell thickness, particularly preferably a cell thickness of preferably 3 μm or less, is required to have a large value of Δn in the above item (3).

【0004】AM−LCDの動作方式では、上下の電極
基盤間における液晶分子の配向を約90°ツイストさせ
たTN表示方式が広く採用されている。このTN表示方
式においては、電圧を印加しない状態での干渉による液
晶セルの着色を防ぎ、かつ、最適なコントラストを得る
ために、屈折率異方性(Δn)とセル厚(d)μmの積
(Δn・d)をある一定の値(例えばΔn・d=〜0.
5μm等)に設定する必要がある。このような制限のも
とで現在実用化されているTFT用液晶組成物のΔnは
ファ−ストミニマム条件で0.07〜0.15程度、特
に0.08〜0.13が主体になっている。E.Jak
emanなど(Phys. Lett., A, 39
(1972)69)によって提唱されているように、応
答時間(以下τと略記することがある)は液晶材料の粘
度(以下ηと略記することがある)に比例し、かつ、セ
ル厚dの2乗に比例する。Δnの大きな液晶組成物を使
用すればセル厚dの値を小さくできるため、τは著しく
低下する。このように液晶表示素子に用いられる液晶組
成物は、適当に大きなΔnを有することが非常に有益で
ある。
In the AM-LCD operation method, a TN display method in which the orientation of liquid crystal molecules between upper and lower electrode substrates is twisted by about 90 ° has been widely adopted. In this TN display system, in order to prevent coloring of the liquid crystal cell due to interference without applying a voltage and to obtain an optimum contrast, the product of the refractive index anisotropy (Δn) and the cell thickness (d) μm is used. (Δn · d) is set to a certain value (for example, Δn · d = 〜0.
5 μm). Under such restrictions, the Δn of the liquid crystal composition for TFTs currently in practical use is about 0.07 to 0.15 under fast minimum conditions, and especially 0.08 to 0.13. I have. E. FIG. Jak
eman et al. (Phys. Lett., A, 39
(1972) 69), the response time (hereinafter sometimes abbreviated as τ) is proportional to the viscosity of the liquid crystal material (hereinafter sometimes abbreviated as η), and the cell thickness d is It is proportional to the square. If a liquid crystal composition having a large Δn is used, the value of the cell thickness d can be reduced, so that τ is significantly reduced. As described above, it is very useful that the liquid crystal composition used for the liquid crystal display element has an appropriately large Δn.

【0005】また、小型軽量で携帯可能なノート型パー
ソナルコンピューター等が開発され、さらにLCDの用
途が広がってきている。携帯用途のLCDは、駆動電源
によって特性の制約を受ける。長時間使用するためには
消費電力を小さくする必要があるので、駆動電力の低電
圧化、すなわち、しきい値電圧の小さい液晶組成物が要
求される。要求される液晶材料のしきい値電圧の値は、
実用化されている5V駆動装置で2.0V程度、4V駆
動装置で1.6V程度である。最近ではさらに低電圧化
を要求されるようになり、しきい値電圧が1.5V以下
の液晶組成物も探求されている。さらには、LCDの小
型化に伴って、屋外での使用を目的とした装置の開発も
検討されている。屋外の使用に耐えうるには、使用環境
の温度範囲を超えた領域にわたってネマティック相を呈
することが要求される。このような観点から現在実用化
されているTFT用液晶組成物は、そのネマティック−
アイソトロピック相転移温度(透明点:TNI)が60
℃以上、スメクティック−ネマティック相転移温度(T
SN)が−20℃以下のものが主体である。
In addition, notebook personal computers and the like that are small and lightweight and portable have been developed, and the use of LCDs has been expanding. LCDs for portable applications are limited in characteristics by the driving power supply. In order to use the device for a long time, it is necessary to reduce power consumption. Therefore, a drive voltage is required to be low, that is, a liquid crystal composition having a small threshold voltage is required. The required threshold voltage value of the liquid crystal material is
The voltage is about 2.0 V for a 5 V driving device that is put into practical use and about 1.6 V for a 4 V driving device. Recently, further lowering of the voltage has been required, and a liquid crystal composition having a threshold voltage of 1.5 V or less has been sought. Furthermore, with the miniaturization of LCDs, the development of devices intended for outdoor use is also being studied. In order to withstand outdoor use, it is required to exhibit a nematic phase over a region beyond the temperature range of the use environment. From this point of view, a liquid crystal composition for a TFT that is currently in practical use is a nematic liquid crystal composition.
Isotropic phase transition temperature (clearing point: T NI ) of 60
° C or higher, smectic-nematic phase transition temperature (T
(SN ) is −20 ° C. or less.

【0006】このような背景に伴って、特表平5−50
0679号公報には、新規な化合物およびその化合物を
用いた液晶組成物が開示されている。しかし、この組成
物の中にはΔnの値が大きいものもあるが、同時にしき
い値電圧が大きすぎ、実用化されている駆動電圧、特に
低電圧駆動には適していない。このように液晶組成物は
種々の目的に応じて鋭意検討されてはいるものの、常に
新規な改良を要求されているのが現状である。
[0006] With such a background, Japanese Patent Application Laid-Open No. 5-50 / 1990.
No. 0679 discloses a novel compound and a liquid crystal composition using the compound. However, some of these compositions have a large value of Δn, but at the same time, have too high a threshold voltage, which is not suitable for a practically used driving voltage, particularly a low voltage driving. As described above, although the liquid crystal composition has been intensively studied for various purposes, it is presently demanding a new improvement.

【0007】[0007]

【発明が解決しようとする課題】本発明者らは、これら
従来の課題を解決すべく、種々の液晶化合物を用いた組
成物について鋭意検討した。その結果、特に高Δnを必
要とするアクティブ・マトリックス方式の液晶表示素子
(AM−LCD表示素子)にも好適に使用される組成物
を見いだし、本発明を完成した。以上の記述から明らか
なように、本発明の目的は、AM−LCD表示素子に求
められる一般的な特性を満たしながら、適当なしきい値
電圧を持ち、特に、高温領域において電圧保持率の高
い、屈折率異方性Δnの大きい液晶組成物,液晶表示素
子を提供することである。
DISCLOSURE OF THE INVENTION The present inventors have intensively studied compositions using various liquid crystal compounds in order to solve these conventional problems. As a result, the present inventors have found a composition which can be suitably used especially for an active matrix type liquid crystal display device (AM-LCD display device) requiring a high Δn, and completed the present invention. As is apparent from the above description, the object of the present invention is to satisfy the general characteristics required for an AM-LCD display element, have an appropriate threshold voltage, and particularly have a high voltage holding ratio in a high temperature region. An object of the present invention is to provide a liquid crystal composition and a liquid crystal display device having a large refractive index anisotropy Δn.

【0008】[0008]

【課題を解決するための手段】本発明は下記によって示
される。 (1)一般式(1)で表される化合物からなる第一成分
および一般式(2−1)〜(2−2)からなる群から選
ばれた少なくとも一種の化合物からなる第二成分を含有
することを特徴とする液晶組成物。 (式中、Rは炭素数1〜10のアルキル基を表し、R
2、R3はそれぞれ独立に炭素数1〜10のアルキル基、
アルコキシ基、アルコキシメチル基もしくは炭素数2〜
10のアルケニル基を表し、Z1、Z2はそれぞれ独立に
-C24-または単結合を表し、XおよびXはそれぞ
れ独立にF、Cl、CF3、OCF3、OCF2H、炭素
数1〜10のアルキル基、アルコキシ基、炭素数2〜1
0のアルコキシメチル基もしくはアルケニル基を表し、
1、Y2、Y3、Y4、Y5、Y6、Y 7、Y8、Y9および
10はそれぞれ独立にHもしくはFを表わす。)。
The present invention is shown by the following.
Is done. (1) A first component comprising a compound represented by the general formula (1)
And the general formulas (2-1) to (2-2).
Contains a second component consisting of at least one compound
A liquid crystal composition comprising:(Where R1Represents an alkyl group having 1 to 10 carbon atoms;
Two, RThreeIs independently an alkyl group having 1 to 10 carbon atoms,
Alkoxy group, alkoxymethyl group or 2-C
10 alkenyl groups, Z1, ZTwoAre independently
-CTwoHFour-Or a single bond, X1And X2Each
Independently F, Cl, CFThree, OCFThree, OCFTwoH, carbon
An alkyl group having 1 to 10 carbon atoms, an alkoxy group, and 2 to 1 carbon atoms
0 represents an alkoxymethyl group or an alkenyl group,
Y1, YTwo, YThree, YFour, YFive, Y6, Y 7, Y8, Y9and
YTenEach independently represents H or F. ).

【0009】(2)さらに、第三成分として、一般式
(3)で表される化合物を少なくとも一種含有すること
を特徴とする前記第1項記載の液晶組成物。 (式中、R4、R5はそれぞれ独立に炭素数1〜10のア
ルキル基、アルコキシ基、炭素数2〜10のアルコキシ
メチル基もしくはアルケニル基を表し、Aは側位のH
がFで置換されていてもよい1,4−フェニレン基を表
し、Aはトランス−1,4−シクロヘキシレン基もし
くは1,4−フェニレン基を表わす。)。
(2) The liquid crystal composition according to the above item 1, further comprising at least one compound represented by the general formula (3) as a third component. (Wherein, R 4 and R 5 each independently represent an alkyl group having 1 to 10 carbon atoms, an alkoxy group, an alkoxymethyl group or an alkenyl group having 2 to 10 carbon atoms, and A 1 represents
There represents a substituted which may be 1,4-phenylene group F, A 2 represents a trans-1,4-cyclohexylene group or 1,4-phenylene group. ).

【0010】(3)液晶組成物の全重量に対して、第一
成分を3〜50重量%、第二成分を3〜90重量%およ
び第三成分を3〜40重量%含有することを特徴とする
前記第2項記載の液晶組成物。
(3) The liquid crystal composition contains the first component in an amount of 3 to 50% by weight, the second component in an amount of 3 to 90% by weight and the third component in an amount of 3 to 40% by weight based on the total weight of the liquid crystal composition. 3. The liquid crystal composition according to the above item 2, wherein

【0011】(4)第二成分が、一般式(2−1―a)
および(2−2―a)からなる群から選ばれた少なくと
も一種の化合物を含有することを特徴とする前記第3項
記載の液晶組成物。 (式中、R2、R3はそれぞれ独立に炭素数1〜10のア
ルキル基、アルコキシ基もしくは炭素数2〜10のアル
ケニル基を表し、XおよびXはそれぞれ独立にF、
Cl、CF3、OCF3、炭素数1〜10のアルキル基、
アルコキシ基もしくは炭素数2〜10のアルケニル基を
表し、Y3、Y4、Y5、Y6、Y9およびY1 0はそれぞれ
独立にHもしくはFを表わす。)。
(4) The second component has the general formula (2-1-a)
4. The liquid crystal composition according to the above item 3, comprising at least one compound selected from the group consisting of and (2-2-a). (Wherein, R 2 and R 3 each independently represent an alkyl group having 1 to 10 carbon atoms, an alkoxy group or an alkenyl group having 2 to 10 carbon atoms, and X 1 and X 2 each independently represent F,
Cl, CF 3 , OCF 3 , an alkyl group having 1 to 10 carbon atoms,
An alkoxy group or an alkenyl group having 2 to 10 carbon atoms, a Y 3, Y 4, Y 5 , Y 6, Y 9 and Y 1 0 each independently H or F. ).

【0012】(5)前記第1項〜第4項のいずれか1項
記載の組成物を用いて構成される液晶表示素子。
(5) A liquid crystal display device comprising the composition according to any one of the above items (1) to (4).

【0013】[0013]

【発明の実施の形態】以下に本発明を詳細に説明する。
本発明の液晶組成物を構成する、第一成分の好ましい化
合物としては、以下の一般式(1−1)〜(1−4)の
いずれかで表される化合物が挙げられる。 これらの式でRは炭素数1〜10のアルキル基を表わ
す。
DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail.
Preferred compounds as the first component constituting the liquid crystal composition of the present invention include compounds represented by any of the following general formulas (1-1) to (1-4). In these formulas, R 1 represents an alkyl group having 1 to 10 carbon atoms.

【0014】つぎに、本発明の第二成分である一般式
(2−1)〜(2−2)の化合物について説明する。一
般式式(2−1)の化合物としては、以下の式(2−1
−1)〜(2−1−26)のいずれかで表わされる化合
物が好ましく用いられる。 これらの式においてR、R’はそれぞれ独立に炭素数
1〜10のアルキル基もしくはアルコキシ基、または炭
素数2〜10のアルコキシメチル基もしくはアルケニル
基を表わす。
Next, the compounds of the general formulas (2-1) to (2-2), which are the second components of the present invention, will be described. As the compound of the general formula (2-1), the following formula (2-1)
Compounds represented by any of -1) to (2-1-26) are preferably used. In these formulas, R 2 and R ′ each independently represent an alkyl group or alkoxy group having 1 to 10 carbon atoms, or an alkoxymethyl group or alkenyl group having 2 to 10 carbon atoms.

【0015】式(2−2)の化合物としては、以下の式
(2−2−1)〜(2−1−33)のいずれかで表わさ
れる化合物が好ましく用いられる。 これらの式においてR、R’はそれぞれ独立に炭素数
1〜10のアルキル基、アルコキシ基、炭素数2〜10
のアルコキシメチル基もしくはアルケニル基を表わす。
As the compound of the formula (2-2), a compound represented by any of the following formulas (2-2-1) to (2-1-33) is preferably used. In these formulas, R 3 and R ′ are each independently an alkyl group having 1 to 10 carbon atoms, an alkoxy group, and a 2 to 10 carbon atoms.
Represents an alkoxymethyl group or an alkenyl group.

【0016】つぎに、本発明の第三成分である一般式
(3)の化合物について説明する。一般式式(3)の化
合物としては、以下の式(3−1)〜(3−2)のいず
れかで表わされる化合物が好ましく用いられる。 式中、R、Rはそれぞれ独立に炭素数1〜10のア
ルキル基、アルコキシ基、炭素数2〜10のアルコキシ
メチル基もしくはアルケニル基を表わす。
Next, the compound of the general formula (3), which is the third component of the present invention, will be described. As the compound of the general formula (3), a compound represented by any of the following formulas (3-1) to (3-2) is preferably used. In the formula, R 4 and R 5 each independently represent an alkyl group having 1 to 10 carbon atoms, an alkoxy group, an alkoxymethyl group having 2 to 10 carbon atoms or an alkenyl group.

【0017】次に本発明の液晶組成物を構成する成分の
化合物の機能について説明する。本発明の第一成分であ
る一般式(1)で表される化合物は、誘電率異方性(Δ
ε)がおよそ15〜20の範囲にあり、透明点(Tc)
がおよそ0〜70℃の範囲、屈折率異方性(Δn)がお
よそ0.1〜0.21の範囲にあり、熱および紫外線の
安定性および化学的安定性に優れている。このため、本
発明の一般式(1)で表される化合物は、特に高信頼性
を要求されるTFT用液晶組成物のΔnを大きくし、か
つ、しきい値電圧を小さくする機能を有する。
Next, the functions of the compounds constituting the liquid crystal composition of the present invention will be described. The compound represented by the general formula (1), which is the first component of the present invention, has a dielectric anisotropy (Δ
ε) is in the range of about 15 to 20, and the clearing point (Tc)
Is in the range of about 0 to 70 ° C., and the refractive index anisotropy (Δn) is in the range of about 0.1 to 0.21, and is excellent in heat and ultraviolet light stability and chemical stability. For this reason, the compound represented by the general formula (1) of the present invention has a function of increasing Δn of a liquid crystal composition for a TFT particularly required to have high reliability and decreasing a threshold voltage.

【0018】本発明の第二成分である一般式(2−1)
で表される化合物は、誘電率異方性(Δε)がおよそ6
〜25の範囲にあり、透明点(Tc)がおよそ−20〜
80℃の範囲、屈折率異方性(Δn)がおよそ0.12
〜0.17の範囲にあり、熱および紫外線の安定性およ
び化学的安定性に優れている。このため、本発明で一般
式(2−1)で表される化合物は、特に高信頼性を要求
されるTFT用液晶組成物のΔnを大きくし、また化合
物の構造によってはしきい値電圧を小さくする機能を有
する。
The general formula (2-1) which is the second component of the present invention
Has a dielectric anisotropy (Δε) of about 6
And the clearing point (Tc) is approximately −20 to
80 ° C. range, refractive index anisotropy (Δn) of about 0.12
0.10.17, which is excellent in heat and ultraviolet light stability and chemical stability. For this reason, the compound represented by the general formula (2-1) in the present invention increases Δn of the liquid crystal composition for a TFT particularly required to have high reliability, and may increase the threshold voltage depending on the structure of the compound. It has a function to make it smaller.

【0019】本発明の第二成分である一般式(2−2)
で表される化合物は、誘電率異方性(Δε)がおよそ7
〜25の範囲にあり、透明点(Tc)がおよそ80〜1
80℃の範囲、屈折率異方性(Δn)がおよそ0.18
〜0.26の範囲にあり、熱および紫外線の安定性およ
び化学的安定性に優れている。このため、本発明で一般
式(2−2)で表される化合物は、特に高信頼性を要求
されるTFT用液晶組成物のΔnを大きくし、かつ透明
点を高くする機能を有する。
The general formula (2-2) which is the second component of the present invention
Has a dielectric anisotropy (Δε) of about 7
And the clearing point (Tc) is about 80 to 1
80 ° C. range, refractive index anisotropy (Δn) of about 0.18
0.20.26, which is excellent in heat and ultraviolet light stability and chemical stability. For this reason, the compound represented by the general formula (2-2) in the present invention has a function of increasing Δn of the liquid crystal composition for TFT, which particularly requires high reliability, and increasing a clearing point.

【0020】本発明の第三成分である一般式(3)で表
される化合物は、誘電率異方性(Δε)がおよそ0であ
り、透明点(Tc)がおよそ220〜270℃の範囲に
あり、屈折率異方性(Δn)がおよそ0.15〜0.2
7の範囲にあり、熱および紫外線の安定性および化学的
安定性に優れている。このため、本発明で一般式(3)
で表される化合物は、特に高信頼性を要求されるTFT
用液晶組成物の透明点を高くする機能を有する。
The compound represented by the general formula (3), which is the third component of the present invention, has a dielectric anisotropy (Δε) of about 0 and a clearing point (Tc) of about 220 to 270 ° C. And the refractive index anisotropy (Δn) is about 0.15 to 0.2
7, which is excellent in heat and ultraviolet light stability and chemical stability. Therefore, in the present invention, the general formula (3)
Is particularly required for TFTs that require high reliability
Has the function of increasing the clearing point of the liquid crystal composition.

【0021】本発明は従来のAM−LCD用液晶組成物
に求められる一般的な特性を満たしながら、適当なしき
い値電圧を持ち、特に、高い信頼性および大きいΔnの
値を持つことを特徴とする液晶組成物である。これらの
特徴を発揮するために、本発明では第一成分および第二
成分、または第一成分、第二成分および第三成分を含有
した構成の液晶組成物になっている。
The present invention is characterized in that it has an appropriate threshold voltage while satisfying general characteristics required for a conventional liquid crystal composition for AM-LCD, and particularly has high reliability and a large value of Δn. Liquid crystal composition. In order to exhibit these features, the present invention provides a liquid crystal composition having a configuration containing a first component and a second component, or a first component, a second component, and a third component.

【0022】以下に、本発明の液晶組成物を構成する化
合物の好ましい成分比並びにその理由について説明す
る。
The preferred component ratios of the compounds constituting the liquid crystal composition of the present invention and the reasons thereof will be described below.

【0023】本発明の第一成分の含有量は液晶組成物の
全重量に対して、3〜50重量%が好ましい。より好ま
しくは、5〜40重量%である。3重量%より少ないと
本発明の目的である、高い信頼性および大きいΔnの値
を持ち、適当なしきい値電圧を持った組成物が得られな
い場合がある。また、第一成分の混合割合が50重量%
を超えると、液晶組成物の粘度が増加する場合や、透明
点(NI点)が低下する場合や、ネマティック相下限温
度(T)が上昇する場合がある。
The content of the first component of the present invention is preferably 3 to 50% by weight based on the total weight of the liquid crystal composition. More preferably, it is 5 to 40% by weight. If the amount is less than 3% by weight, a composition having high reliability and a large value of Δn, which is the object of the present invention, and having an appropriate threshold voltage may not be obtained. Also, the mixing ratio of the first component is 50% by weight.
By weight, and the viscosity of the liquid crystal composition is increased, and if the clearing point (NI point) is lowered, there is a case where the nematic phase lower limit temperature (T C) is increased.

【0024】本発明の第二成分の含有量は液晶組成物の
全重量に対して、3〜90重量%が好ましい。より好ま
しくは、5〜80重量%である。3重量%より少ないと
本発明の目的である、適当なしきい値電圧を持ち、高い
信頼性および大きいΔnの値を持った組成物が得られな
い場合がある。また、第二成分の混合割合が90重量%
を超えると、液晶組成物の粘度が増加する場合や、透明
点(NI点)が低下する場合や、ネマティック相下限温
度(T)が上昇する場合がある。
The content of the second component of the present invention is preferably 3 to 90% by weight based on the total weight of the liquid crystal composition. More preferably, it is 5 to 80% by weight. If the amount is less than 3% by weight, a composition having an appropriate threshold voltage, high reliability and a large value of Δn, which is the object of the present invention, may not be obtained. The mixing ratio of the second component is 90% by weight.
By weight, and the viscosity of the liquid crystal composition is increased, and if the clearing point (NI point) is lowered, there is a case where the nematic phase lower limit temperature (T C) is increased.

【0025】本発明の第三成分の含有量は液晶組成物の
全重量に対して、3〜40重量%が好ましい。より好ま
しくは、5〜30重量%である。該第三成分の混合割合
が40重量%を超えると、液晶組成物の粘度が増加する
場合や、しきい値電圧が上昇する場合や、ネマティック
相下限温度(T)が上昇する場合がある。
The content of the third component of the present invention is preferably 3 to 40% by weight based on the total weight of the liquid crystal composition. More preferably, it is 5 to 30% by weight. If the mixing ratio of said third component exceeds 40 wt%, and the viscosity of the liquid crystal composition is increased, and if the threshold voltage is increased, there is a case where the nematic phase lower limit temperature (T C) increases .

【0026】本発明の液晶組成物には、本発明の目的を
害さない範囲で、しきい値電圧、ネマティック温度範
囲、Δn、Δε等を調整する目的で、前記に示した一般
式で表される化合物以外の液晶化合物を混合して使用す
ることもできる。本発明の液晶組成物は、それ自体慣用
な方法で調製される。一般には、種々の成分化合物を混
合し、高い温度で互いに溶解させる方法がとられる。本
発明の液晶組成物には、液晶分子のらせん構造を誘起し
て必要なねじれ角を得るためにキラルドープ剤を添加し
て使用することもできる。
The liquid crystal composition of the present invention is represented by the general formula shown above for the purpose of adjusting the threshold voltage, the nematic temperature range, Δn, Δε, etc. within a range that does not impair the purpose of the present invention. Liquid crystal compounds other than the above compounds may be used in combination. The liquid crystal composition of the present invention is prepared by a conventional method. Generally, a method is used in which various component compounds are mixed and dissolved at a high temperature. The liquid crystal composition of the present invention can be used by adding a chiral dopant to induce a helical structure of liquid crystal molecules and obtain a required twist angle.

【0027】本発明の液晶組成物は、メロシアニン系、
スチリル系、アゾ系、アゾメチン系、アゾキシ系、キノ
フタロン系、アントラキノン系およびテトラジン系の二
色性色素を添加してゲストホスト(GH)モードの液晶
組成物としても使用することができる。また、本発明の
液晶組成物は、Δn・dがセカンドミニマム系(例えば
Δn・d=〜1μm等)のAM−LCD用の液晶組成物
としても使用することができる。さらには、ネマティッ
ク液晶をマイクロカプセル化して作成したNCAPや、
液晶中に三次元網目状高分子を作成したポリマーネット
ワーク液晶表示素子(PNLCD)に代表されるポリマ
ー分散型液晶表示素子(PDLCD)用の液晶組成物と
しても使用することができる。その他、イン・プレイン
・スイッチング(IPS)方式やOCB等の複屈折制御
(ECB)モード用および動的散乱(DS)モード用の
液晶組成物としても使用することができる。
The liquid crystal composition of the present invention comprises a merocyanine compound,
A styryl-based, azo-based, azomethine-based, azoxy-based, quinophthalone-based, anthraquinone-based, and tetrazine-based dichroic dye can be added to be used as a guest-host (GH) mode liquid crystal composition. Further, the liquid crystal composition of the present invention can also be used as a liquid crystal composition for AM-LCD of which Δnd has a second minimum (for example, Δnd = ・ 1 μm). Furthermore, NCAP made by microencapsulating nematic liquid crystal,
It can also be used as a liquid crystal composition for a polymer dispersed liquid crystal display (PDLCD) represented by a polymer network liquid crystal display (PNLCD) in which a three-dimensional network polymer is formed in a liquid crystal. In addition, it can be used as a liquid crystal composition for an in-plane switching (IPS) mode, a birefringence control (ECB) mode such as OCB, and a dynamic scattering (DS) mode.

【0028】[0028]

【実施例】以下に、実施例により本発明を詳細に説明す
るが、これらの実施例に限定されるものではない。比較
例および実施例に示した成分の混合割合は全て重量%を
示す。比較例および実施例で用いられる化合物は、表1
に示した定義に基づいて、記号により表わした。
The present invention will be described below in detail with reference to examples, but the present invention is not limited to these examples. The mixing ratios of the components shown in Comparative Examples and Examples are all by weight. Compounds used in Comparative Examples and Examples are shown in Table 1.
Are represented by symbols based on the definitions shown in Table 1.

【0029】[0029]

【表1】 [Table 1]

【0030】液晶組成物の特性は、以下のように測定し
求めた。ネマチック液晶相の上限温度TNIは、偏光顕
微鏡を用いて、昇温過程において、ネマチック相から等
方性液体相に変化するとき状態を観察して、その温度を
測定することにより求めた。ネマチック液晶相の下限温
度Tは、0℃、−10℃、−20℃、および−30℃
のそれぞれの温度に保ったフリーザー中に、液晶組成物
を30日間放置し、結晶もしくはスメクチック相が出現
するフリーザーの温度で判断した。例えば、一つの液晶
組成物について、−20℃でネマチック状態をとり、−
30℃で結晶化またはスメクチック状態となった場合に
は、その液晶組成物のTは、<−20℃と表現した。
The characteristics of the liquid crystal composition were measured and determined as follows. The maximum temperature T NI of the nematic liquid crystal phase was determined by observing the state of the nematic liquid crystal phase when it changes from a nematic phase to an isotropic liquid phase in a heating process using a polarizing microscope, and measuring the temperature. Lower limit temperature T C of a nematic liquid crystal phase, 0 ℃, -10 ℃, -20 ℃, and -30 ° C.
The liquid crystal composition was allowed to stand for 30 days in the freezer maintained at each temperature, and the temperature of the freezer at which a crystal or a smectic phase appeared was determined. For example, one liquid crystal composition takes a nematic state at −20 ° C.,
When a crystallization or smectic state at 30 ° C., the T C of the liquid crystal composition <- is expressed as 20 ° C..

【0031】屈折率異方性Δnは、589nmの波長を
有する光源ランプを使用し、アッベ屈折計を用いて25
℃で測定した。誘電率異方性Δεは25℃で測定した。
しきい値電圧Vthは、セル厚d=約9μmの80°ツ
イストセルに注入し、25℃で測定したV−T曲線から
求めた。
The refractive index anisotropy Δn is determined by using a light source lamp having a wavelength of 589 nm and measuring the refractive index anisotropy Δn by using an Abbe refractometer.
Measured in ° C. The dielectric anisotropy Δε was measured at 25 ° C.
The threshold voltage Vth was obtained from a VT curve measured at 25 ° C. by injecting into an 80 ° twist cell having a cell thickness d of about 9 μm.

【0032】電圧保持率VHRの測定は、日本電子機会
工業会規格EIAJ ED−2521Aで規定される液
晶材料および配向膜の電圧保持率測定法に準じて面積法
にて行った。この測定方法は、特開平5−331464
号公報にも記載されている。すなわち、試料の液晶組成
物をポリイミド系配向膜を設けたセル厚6μmのTNセ
ルに封入して作成した液晶素子に、波高値±5V、パル
ス幅60μsのパルス電圧を、周期30Hzの交流電圧
として印可したときの、該液晶素子の電極間電圧波形を
陰極線オシロスコープで観測する。単位周期における該
印可電圧と周期の積(面積)に対する観測電圧の絶対値
の積算値(面積)との割合を百分率で表し、電圧保持率
とした。
The voltage holding ratio VHR was measured by an area method according to the method for measuring the voltage holding ratio of a liquid crystal material and an alignment film specified by EIAJ ED-2521A of the Japan Electronic Opportunities Manufacturers Association. This measuring method is disclosed in
It is also described in the official gazette. That is, a liquid crystal element prepared by enclosing a liquid crystal composition of a sample in a TN cell having a cell thickness of 6 μm provided with a polyimide-based alignment film was subjected to a pulse voltage of a peak value of ± 5 V and a pulse width of 60 μs as an AC voltage having a cycle of 30 Hz. The voltage waveform between the electrodes of the liquid crystal element at the time of application is observed with a cathode ray oscilloscope. The ratio of the integrated value (area) of the absolute value of the observed voltage to the product (area) of the applied voltage and the period in a unit cycle was expressed as a percentage, and was defined as a voltage holding ratio.

【0033】比較例1 本願発明の組成物と類似の組成物として、特開平10−
95978号公報の中で最もΔnが大きい組成物として
実施例5が開示されている。この組成は以下の通りであ
る。本発明における一般式(1)の類似(同等ではな
い)の化合物として、 3−BB(F)B(F,F)−OCF3 7% 3−BB(F,F)2B(F,F)−CL 7% 3−B(F)BB(F,F)−F 10% 3−BB(F,F)B(F,F)−CL 8% その他の成分として、 3−H2HB(F,F)−F 9% 4−H2HB(F,F)−F 8% 3−H2HB−OCF3 2% 3−HHB(F,F)−F 10% 4−HHB(F,F)−F 5% 3−HBB(F,F)−F 27% 3−HB(F,F)B(F)−F 2% 3−HHBB(F,F)−F 5% 上記組成物の特性は、以下の通りである。 TNI = 62.5℃ T < −30℃ Δn = 0.128 Vth = 0.86V VHR(25℃) = 99.3% VHR(100℃) = 96.2% 本発明における一般式(1)に類似の化合物を含むこの
組成は、本発明の組成物と比べて、かなりΔnが小さ
く、また、透明点TNIが低いという欠点を有する。
Comparative Example 1 As a composition similar to the composition of the present invention,
Example 5 discloses a composition having the largest Δn in US Pat. This composition is as follows. As a similar (but not equivalent) compound of the general formula (1) in the present invention, 3-BB (F) B (F, F) -OCF3 7% 3-BB (F, F) 2B (F, F)- CL 7% 3-B (F) BB (F, F) -F 10% 3-BB (F, F) B (F, F) -CL 8% As other components, 3-H2HB (F, F) -F 9% 4-H2HB (F, F) -F 8% 3-H2HB-OCF3 2% 3-HHB (F, F) -F 10% 4-HHB (F, F) -F 5% 3-HBB (F, F) -F 27% 3-HB (F, F) B (F) -F 2% 3-HHBB (F, F) -F 5% The characteristics of the composition are as follows. T NI = 62.5 ℃ T C < -30 ℃ Δn = 0.128 Vth = 0.86V VHR (25 ℃) = 99.3% VHR formula at (100 ℃) = 96.2% The present invention (1 This composition, which contains compounds analogous to (1), has the disadvantage that, compared to the composition according to the invention, the Δn is considerably lower and the clearing point T NI is lower.

【0034】比較例2 本願発明の組成物と類似の組成物として、特開平8−7
3857号公報の中で最もΔnが大きい組成物として実
施例7が開示されている。この組成を調製した。 2−HBEB(F,F)−F 5% 5−HBEB(F,F)−F 5% 3−BBEB(F,F)−F 5% 4−HHB−CL 10% 3−HHB(F,F)−F 10% 5−HHB(F,F)−F 10% 3−H2BB(F,F)−F 10% 4−H2BB(F,F)−F 10% 5−H2BB(F,F)−F 10% 3−HVHB(F)−F 5% 4−HVHB(F,F)−F 7% 3−H2BVB−2 3% 3−HB(F)VB−4 10% 上記組成物の特性は、以下の通りである。 TNI = 101.5℃ Δn = 0.138 Vth = 1.73V VHR(25℃) = 98.5% VHR(100℃) = 91.0% この組成は、本発明の組成物と比べて、Δnが小さく、
高温でのVHRが低いという欠点を有する。
Comparative Example 2 As a composition similar to the composition of the present invention, JP-A-8-7
Example 7 discloses a composition having the largest Δn in 3857. This composition was prepared. 2-HBEB (F, F) -F 5% 5-HBEB (F, F) -F 5% 3-BBEB (F, F) -F 5% 4-HHB-CL 10% 3-HHB (F, F ) -F 10% 5-HHB (F, F) -F 10% 3-H2BB (F, F) -F 10% 4-H2BB (F, F) -F 10% 5-H2BB (F, F)- F 10% 3-HVHB (F) -F 5% 4-HVHB (F, F) -F 7% 3-H2BVB-2 3% 3-HB (F) VB-4 10% It is as follows. T NI = 101.5 ° C. Δn = 0.138 Vth = 1.73V VHR (25 ° C.) = 98.5% VHR (100 ° C.) = 91.0% This composition is compared with the composition of the present invention. Δn is small,
It has the disadvantage of low VHR at high temperatures.

【0035】比較例3 DE 3921836号公報に開示されている以下の組
成物を調製した。本発明における一般式(3)で表され
る化合物として、 5−HBB(F)B−3 10% その他の成分として、 ZLI−1565(メルク社製) 90% 上記組成物の特性は、以下の通りである。 TNI = 117.0℃ T < −20℃ Δn = 0.163 Vth = 2.63V Δε = 7.9 VHR(25℃) = 96.8% VHR(100℃) = 92.2% この組成は、本発明の組成物と比べて、Δnが小さく、
しきい値電圧Vthが非常に大きく低電圧駆動には適さ
ないという欠点を有する。
Comparative Example 3 The following composition disclosed in DE 3921836 was prepared. As a compound represented by the general formula (3) in the present invention, 5-HBB (F) B-3 10% As other components, ZLI-1565 (manufactured by Merck) 90% The characteristics of the above composition are as follows. It is on the street. T NI = 117.0 ℃ T C < -20 ℃ Δn = 0.163 Vth = 2.63V Δε = 7.9 VHR (25 ℃) = 96.8% VHR (100 ℃) = 92.2% The composition Has a smaller Δn than the composition of the present invention,
There is a disadvantage that the threshold voltage Vth is very large and is not suitable for low voltage driving.

【0036】 実施例1 本発明における一般式(1)で表される化合物として、 5−BBB(F,F)−F 5% 一般式(2−1)で表される化合物として、 3−BB(F,F)CF2OB(F,F)−F 20% 一般式(2−2)で表される化合物として、 3−BB(F,F)CF2OBB−5 10% 5−BB(F,F)CF2OBB−2 5% 一般式(3)で表される化合物として、 5−HBB(F)B−2 10% 5−HBB(F)B−3 10% その他の成分として、 3−HBB(F,F)−F 30% 5−HBB(F,F)−F 10% 上記組成物の特性は、以下のようであった。 TNI = 114.0℃ T < −20℃ Δn = 0.178 Vth = 1.89V Δε = 10.7 VHR(25℃) = 99.3% VHR(100℃) = 96.4%Example 1 As a compound represented by the general formula (1) in the present invention, 5-BBB (F, F) -F 5% As a compound represented by the general formula (2-1), 3-BB (F, F) CF2OB (F, F) -F 20% As a compound represented by the general formula (2-2), 3-BB (F, F) CF2OBB-5 10% 5-BB (F, F) CF2OBB-2 5% As a compound represented by the general formula (3), 5-HBB (F) B-2 10% 5-HBB (F) B-3 10% As other components, 3-HBB (F, F) -F 30% 5-HBB (F, F) -F 10% The properties of the composition were as follows. T NI = 114.0 ℃ T C < -20 ℃ Δn = 0.178 Vth = 1.89V Δε = 10.7 VHR (25 ℃) = 99.3% VHR (100 ℃) = 96.4%

【0037】 実施例2 本発明における一般式(1)で表される化合物として、 3−BBB(F,F)−F 5% 一般式(2−1)で表される化合物として、 3−BB(F,F)CF2OB(F,F)−F 20% 一般式(2−2)で表される化合物として、 3−BB(F,F)CF2OBB−5 5% 5−BB(F,F)CF2OBB−2 5% 2−BB(F,F)CF2OBB−5 5% 一般式(3)で表される化合物として、 5−HBB(F)B−2 10% 5−HBB(F)B−3 10% その他の成分として、 3−HBB(F,F)−F 20% 5−HBB(F,F)−F 20% 上記組成物の特性は、以下のようになった。 TNI = 114.3℃ T < −30℃ Δn = 0.178 Vth = 1.85V Δε = 11.1 VHR(25℃) = 99.2% VHR(100℃) = 96.3%Example 2 As a compound represented by the general formula (1) in the present invention, 3-BBB (F, F) -F 5% As a compound represented by the general formula (2-1), 3-BB (F, F) CF2OB (F, F) -F 20% As a compound represented by the general formula (2-2), 3-BB (F, F) CF2OBB-5 5% 5-BB (F, F) CF2OBB-2 5% 2-BB (F, F) CF2OBB-5 5% As a compound represented by the general formula (3), 5-HBB (F) B-2 10% 5-HBB (F) B-3 10% As other components, 3-HBB (F, F) -F 20% 5-HBB (F, F) -F 20% The characteristics of the composition were as follows. T NI = 114.3 ℃ T C < -30 ℃ Δn = 0.178 Vth = 1.85V Δε = 11.1 VHR (25 ℃) = 99.2% VHR (100 ℃) = 96.3%

【0038】 実施例3 本発明における一般式(1)で表される化合物として、 3−BBB(F,F)−F 5% 一般式(2−1)で表される化合物として、 3−BB(F,F)CF2OB(F,F)−F 30% 5−BB(F,F)CF2OB(F,F)−F 10% 一般式(2−2)で表される化合物として、 3−BB(F,F)CF2OBB−5 5% 5−BB(F,F)CF2OBB−2 5% 2−BB(F,F)CF2OBB−5 5% 一般式(3)で表される化合物として、 5−HBB(F)B−2 10% 5−HBB(F)B−3 10% その他の成分として、 3−HBB(F,F)−F 20% 上記組成物の特性は、以下のようになった。 TNI = 107.5℃ T < −30℃ Δn = 0.177 Vth = 1.70V Δε = 12.6 VHR(25℃) = 98.2% VHR(100℃) = 96.2%Example 3 As a compound represented by the general formula (1) in the present invention, 3-BBB (F, F) -F 5% As a compound represented by the general formula (2-1), 3-BB (F, F) CF2OB (F, F) -F 30% 5-BB (F, F) CF2OB (F, F) -F 10% As a compound represented by the general formula (2-2), 3-BB (F, F) CF2OBB-5 5% 5-BB (F, F) CF2OBB-5 5% 2-BB (F, F) CF2OBB-5 5% As a compound represented by the general formula (3), HBB (F) B-2 10% 5-HBB (F) B-3 10% As other components, 3-HBB (F, F) -F 20% The characteristics of the above composition were as follows. . T NI = 107.5 ℃ T C < -30 ℃ Δn = 0.177 Vth = 1.70V Δε = 12.6 VHR (25 ℃) = 98.2% VHR (100 ℃) = 96.2%

【0039】 実施例4 本発明における一般式(1)で表される化合物として、 3−BBB(F,F)−F 5% 3−BB2B(F,F)−F 10% 3−B2BB(F,F)−F 10% 一般式(2−1)で表される化合物として、 3−BB(F,F)CF2OB(F,F)−F 20% 3−BB(F,F)CF2OB−F 5% 3−BB(F,F)CF2OB−2 5% 一般式(2−2)で表される化合物として、 3−BB(F,F)CF2OBB−5 5% 5−BB(F,F)CF2OBB−2 5% 2−BB(F,F)CF2OBB−5 5% 5−BB(F,F)CF2OBB−3 5% 5−BB(F,F)CF2OBB−5 5% 一般式(3)で表される化合物として、 5−HBB(F)B−2 5% 5−HBB(F)B−3 5% その他の成分として、 3−HBB(F,F)−F 10% 上記組成物の特性は、以下のようになった。 TNI = 96.6℃ T < −30℃ Δn = 0.183 Vth = 1.59V Δε = 13.2 VHR(25℃) = 98.6% VHR(100℃) = 95.0%Example 4 As a compound represented by the general formula (1) in the present invention, 3-BBB (F, F) -F 5% 3-BB2B (F, F) -F 10% 3-B2BB (F , F) -F 10% As a compound represented by the general formula (2-1), 3-BB (F, F) CF2OB (F, F) -F 20% 3-BB (F, F) CF2OB-F 5% 3-BB (F, F) CF2OB-2 5% As a compound represented by the general formula (2-2), 3-BB (F, F) CF2OBB-5 5% 5-BB (F, F) CF2OBB-2 5% 2-BB (F, F) CF2OBB-5 5% 5-BB (F, F) CF2OBB-3 5% 5-BB (F, F) CF2OBB-5 5% In the general formula (3) As a compound represented, 5-HBB (F) B-2 5% 5-HBB (F) B-3 5% As other components, Characteristics of -HBB (F, F) -F 10% above composition were as follows. T NI = 96.6 ℃ T C < -30 ℃ Δn = 0.183 Vth = 1.59V Δε = 13.2 VHR (25 ℃) = 98.6% VHR (100 ℃) = 95.0%

【0040】 実施例5 本発明における一般式(1)で表される化合物として、 3−BBB(F,F)−F 3% 3−BB2B(F,F)−F 10% 3−B2BB(F,F)−F 10% 一般式(2−1)で表される化合物として、 2−BB(F,F)CF2OB(F,F)−F 2% 3−BB(F,F)CF2OB(F,F)−F 20% 5−BB(F,F)CF2OB(F,F)−F 10% 一般式(2−2)で表される化合物として、 3−BB(F,F)CF2OBB−5 5% 5−BB(F,F)CF2OBB−2 5% 2−BB(F,F)CF2OBB−5 5% 5−BB(F,F)CF2OBB−F 5% 一般式(3)で表される化合物として、 5−HBB(F)B−2 5% 5−HBBH−3 5% 5−HB(F)BH−3 5% その他の成分として、 2−HBB(F)−F 2.5% 3−HBB(F)−F 2.5% 5−HBB(F)−F 5% 上記組成物の特性は、以下のようになった。 TNI = 100.8℃ T < −20℃ Δn = 0.172 Vth = 1.57V Δε = 13.9 VHR(25℃) = 98.7% VHR(100℃) = 95.2%Example 5 As a compound represented by the general formula (1) in the present invention, 3-BBB (F, F) -F 3% 3-BB2B (F, F) -F 10% 3-B2BB (F , F) -F 10% As a compound represented by the general formula (2-1), 2-BB (F, F) CF2OB (F, F) -F 2% 3-BB (F, F) CF2OB (F , F) -F 20% 5-BB (F, F) CF2OB (F, F) -F 10% As a compound represented by the general formula (2-2), 3-BB (F, F) CF2OBB-5 5% 5-BB (F, F) CF2OBB-2 5% 2-BB (F, F) CF2OBB-5 5% 5-BB (F, F) CF2OBB-F 5% Represented by the general formula (3) As a compound, 5-HBB (F) B-2 5% 5-HBBH-3 5% 5-HB (F) BH-3 5% As other components Characteristics of 2-HBB (F) -F 2.5% 3-HBB (F) -F 2.5% 5-HBB (F) -F 5% above composition were as follows. T NI = 100.8 ℃ T C < -20 ℃ Δn = 0.172 Vth = 1.57V Δε = 13.9 VHR (25 ℃) = 98.7% VHR (100 ℃) = 95.2%

【0041】 実施例6 本発明における一般式(1)で表される化合物として、 3−BBB(F,F)−F 5% 3−BB2B(F,F)−F 10% 3−B2BB(F,F)−F 10% 一般式(2−1)で表される化合物として、 3−BB(F,F)CF2OB(F,F)−F 20% 一般式(2−2)で表される化合物として、 3−BB(F,F)CF2OBB−5 5% 5−BB(F,F)CF2OBB−2 5% 2−BB(F,F)CF2OBB−5 5% 一般式(3)で表される化合物として、 5−HBB(F)B−2 5% 5−HBB(F)B−3 5% その他の成分として、 2−HBB(F)−F 10% 3−HBB(F)−F 10% 5−HBB(F)−F 10% 上記組成物の特性は、以下のようになった。 TNI = 117.6℃ T < −30℃ Δn = 0.188 Vth = 1.79V Δε = 11.0 VHR(25℃) = 98.9% VHR(100℃) = 95.6%Example 6 As a compound represented by the general formula (1) in the present invention, 3-BBB (F, F) -F 5% 3-BB2B (F, F) -F 10% 3-B2BB (F , F) -F 10% As a compound represented by the general formula (2-1), 3-BB (F, F) CF2OB (F, F) -F 20% represented by the general formula (2-2) As a compound, 3-BB (F, F) CF2OBB-5 5% 5-BB (F, F) CF2OBB-2 5% 2-BB (F, F) CF2OBB-5 5% It is represented by the general formula (3). 5-HBB (F) B-2 5% 5-HBB (F) B-3 5% As other components, 2-HBB (F) -F 10% 3-HBB (F) -F10 % 5-HBB (F) -F 10% The characteristics of the composition were as follows. T NI = 117.6 ℃ T C < -30 ℃ Δn = 0.188 Vth = 1.79V Δε = 11.0 VHR (25 ℃) = 98.9% VHR (100 ℃) = 95.6%

【0042】 実施例7 本発明における一般式(1)で表される化合物として、 3−BBB(F,F)−F 5% 3−BB2B(F,F)−F 10% 3−B2BB(F,F)−F 10% 一般式(2−1)で表される化合物として、 3−BB(F,F)CF2OB(F,F)−F 20% 3−BB(F,F)CF2OB(F)−OCF3 5% 一般式(2−2)で表される化合物として、 3−BB(F,F)CF2OBB−5 5% 5−BB(F,F)CF2OBB−2 5% 2−BB(F,F)CF2OBB−5 5% 5−BB(F,F)CF2OBB−3 5% 5−BB(F,F)CF2OBB−F 5% 5−BB(F,F)CF2OBB(F)−F 5% 3−BB(F,F)CF2OBB−F 5% 5−BB(F,F)CF2OBB−5 5% その他の成分として、 3−HBB(F,F)−F 10% 上記組成物の特性は、以下のようになった。 TNI = 93.1℃ T < −30℃ Δn = 0.184 Vth = 1.49V Δε = 14.5 VHR(25℃) = 98.5% VHR(100℃) = 94.8%Example 7 As a compound represented by the general formula (1) in the present invention, 3-BBB (F, F) -F 5% 3-BB2B (F, F) -F 10% 3-B2BB (F , F) -F 10% As a compound represented by the general formula (2-1), 3-BB (F, F) CF2OB (F, F) -F 20% 3-BB (F, F) CF2OB (F ) -OCF3 5% As a compound represented by the general formula (2-2), 3-BB (F, F) CF2OBB-5 5% 5-BB (F, F) CF2OBB-2 5% 2-BB (F , F) CF2OBB-5 5% 5-BB (F, F) CF2OBB-3 5% 5-BB (F, F) CF2OBB-F 5% 5-BB (F, F) CF2OBB (F) -F 5% 3-BB (F, F) CF2OBB-F 5% 5-BB (F, F) CF2OBB-5-5% Other components , Characteristic of the 3-HBB (F, F) -F 10% above composition were as follows. T NI = 93.1 ℃ T C < -30 ℃ Δn = 0.184 Vth = 1.49V Δε = 14.5 VHR (25 ℃) = 98.5% VHR (100 ℃) = 94.8%

【0043】 実施例8 本発明における一般式(1)で表される化合物として、 3−BBB(F,F)−F 5% 3−BB2B(F,F)−F 10% 3−B2BB(F,F)−F 10% 一般式(2−1)で表される化合物として、 3−BB(F,F)CF2OB(F,F)−F 20% 3−BBCF2OB(F,F)−F 10% 一般式(2−2)で表される化合物として、 3−BB(F,F)CF2OBB−5 5% 5−BB(F,F)CF2OBB−2 5% 2−BB(F,F)CF2OBB−5 5% 一般式(3)で表される化合物として、 5−HBB(F)B−2 10% 5−HBB(F)B−3 10% その他の成分として、 2−HBB−F 3% 3−HBB−F 4% 5−HBB−F 3% 上記組成物の特性は、以下のようになった。 TNI = 113.6℃ T < −30℃ Δn = 0.189 Vth = 1.65V Δε = 12.6 VHR(25℃) = 98.7% VHR(100℃) = 95.2%Example 8 As a compound represented by the general formula (1) in the present invention, 3-BBB (F, F) -F 5% 3-BB2B (F, F) -F 10% 3-B2BB (F , F) -F 10% As a compound represented by the general formula (2-1), 3-BB (F, F) CF2OB (F, F) -F 20% 3-BBCF2OB (F, F) -F10 % As a compound represented by the general formula (2-2), 3-BB (F, F) CF2OBB-5 5% 5-BB (F, F) CF2OBB-2 5% 2-BB (F, F) CF2OBB -5 5% As a compound represented by the general formula (3), 5-HBB (F) B-2 10% 5-HBB (F) B-3 10% As another component, 2-HBB-F 3% 3-HBB-F 4% 5-HBB-F 3% The characteristics of the composition were as follows. T NI = 113.6 ℃ T C < -30 ℃ Δn = 0.189 Vth = 1.65V Δε = 12.6 VHR (25 ℃) = 98.7% VHR (100 ℃) = 95.2%

【0044】 実施例9 本発明における一般式(1)で表される化合物として、 3−BBB(F,F)−F 5% 3−BB2B(F,F)−F 10% 3−B2BB(F,F)−F 5% 一般式(2−1)で表される化合物として、 3−BB(F,F)CF2OB(F,F)−F 15% 3−BB(F,F)CF2OB(F)−OCF3 10% 3−BB(F,F)CF2OB(F)−F 15% 一般式(2−2)で表される化合物として、 3−BB(F,F)CF2OBB−5 10% 5−BB(F,F)CF2OBB−2 5% 2−BB(F,F)CF2OBB−5 5% 5−BB(F,F)CF2OBB−3 5% 5−BB(F,F)CF2OBB−5 5% 一般式(3)で表される化合物として、 5−HBB(F)B−2 5% 5−HBB(F)B−3 5% 上記組成物の特性は、以下のようになった。 TNI = 82.8℃ T < −30℃ Δn = 0.187 Vth = 1.34V Δε = 14.7 VHR(25℃) = 98.5% VHR(100℃) = 94.9%Example 9 As a compound represented by the general formula (1) in the present invention, 3-BBB (F, F) -F 5% 3-BB2B (F, F) -F 10% 3-B2BB (F , F) -F 5% As a compound represented by the general formula (2-1), 3-BB (F, F) CF2OB (F, F) -F 15% 3-BB (F, F) CF2OB (F ) -OCF3 10% 3-BB (F, F) CF2OB (F) -F 15% As a compound represented by the general formula (2-2), 3-BB (F, F) CF2OBB-5 10% 5- BB (F, F) CF2OBB-2 5% 2-BB (F, F) CF2OBB-5 5% 5-BB (F, F) CF2OBB-3 5% 5-BB (F, F) CF2OBB-5 5% As the compound represented by the general formula (3), 5-HBB (F) B-2 5% 5-HBB (F) B-3 5% The properties of the composition were as follows. T NI = 82.8 ℃ T C < -30 ℃ Δn = 0.187 Vth = 1.34V Δε = 14.7 VHR (25 ℃) = 98.5% VHR (100 ℃) = 94.9%

【0045】 実施例10 本発明における一般式(1)で表される化合物として、 3−BBB(F,F)−F 5% 3−BB2B(F,F)−F 10% 3−B2BB(F,F)−F 10% 一般式(2−1)で表される化合物として、 3−BB(F,F)CF2OB(F,F)−F 20% 5−BB(F,F)CF2OB(F,F)−F 10% 一般式(2−2)で表される化合物として、 3−BB(F,F)CF2OBB−5 10% 5−BB(F,F)CF2OBB−2 5% 2−BB(F,F)CF2OBB−5 5% 5−BB(F,F)CF2OBB−3 5% 5−BB(F,F)CF2OBB−F 5% 3−BB(F,F)CF2OBB−F 5% 5−BB(F,F)CF2OBB−5 10% 上記組成物の特性は、以下のようになった。 TNI = 95.0℃ T < −30℃ Δn = 0.189 Vth = 1.44V Δε = 14.2 VHR(25℃) = 98.6% VHR(100℃) = 95.1%Example 10 As a compound represented by the general formula (1) in the present invention, 3-BBB (F, F) -F 5% 3-BB2B (F, F) -F 10% 3-B2BB (F , F) -F 10% As a compound represented by the general formula (2-1), 3-BB (F, F) CF2OB (F, F) -F 20% 5-BB (F, F) CF2OB (F , F) -F 10% As a compound represented by the general formula (2-2), 3-BB (F, F) CF2OBB-5 10% 5-BB (F, F) CF2OBB-2 5% 2-BB (F, F) CF2OBB-5 5% 5-BB (F, F) CF2OBB-3 5% 5-BB (F, F) CF2OBB-F 5% 3-BB (F, F) CF2OBB-F 5% 5 -BB (F, F) CF2OBB-5 10% The properties of the composition were as follows. T NI = 95.0 ℃ T C < -30 ℃ Δn = 0.189 Vth = 1.44V Δε = 14.2 VHR (25 ℃) = 98.6% VHR (100 ℃) = 95.1%

【0046】 実施例11 本発明における一般式(1)で表される化合物として、 3−BBB(F,F)−F 5% 3−BB2B(F,F)−F 10% 3−B2BB(F,F)−F 10% 一般式(2−1)で表される化合物として、 3−BB(F,F)CF2OB(F,F)−F 20% 3−BB(F,F)CF2OB(F,F)−OCF3 10% 3−BBCF2OB(F,F)−F 10% 一般式(2−2)で表される化合物として、 3−BB(F,F)CF2OBB−5 5% 5−BB(F,F)CF2OBB−2 5% 2−BB(F,F)CF2OBB−5 5% 一般式(3)で表される化合物として、 5−HBB(F)B−2 10% 5−HBB(F)B−3 10% 上記組成物の特性は、以下のようになった。 TNI = 103.7℃ T < −30℃ Δn = 0.186 Vth = 1.46V Δε = 14.9 VHR(25℃) = 98.5% VHR(100℃) = 94.8%Example 11 As a compound represented by the general formula (1) in the present invention, 3-BBB (F, F) -F 5% 3-BB2B (F, F) -F 10% 3-B2BB (F , F) -F 10% As a compound represented by the general formula (2-1), 3-BB (F, F) CF2OB (F, F) -F 20% 3-BB (F, F) CF2OB (F , F) -OCF3 10% 3-BBCF2OB (F, F) -F 10% As a compound represented by the general formula (2-2), 3-BB (F, F) CF2OBB-5 5% 5-BB ( F, F) CF2OBB-2 5% 2-BB (F, F) CF2OBB-5 5% As a compound represented by the general formula (3), 5-HBB (F) B-2 10% 5-HBB (F ) B-3 10% The properties of the composition were as follows. T NI = 103.7 ℃ T C < -30 ℃ Δn = 0.186 Vth = 1.46V Δε = 14.9 VHR (25 ℃) = 98.5% VHR (100 ℃) = 94.8%

【0047】 実施例12 本発明における一般式(1)で表される化合物として、 3−BBB(F,F)−F 3% 3−BB2B(F,F)−F 10% 3−B2BB(F,F)−F 10% 一般式(2−1)で表される化合物として、 2−BB(F,F)CF2OB(F,F)−F 2% 3−BB(F,F)CF2OB(F,F)−F 20% 5−BB(F,F)CF2OB(F,F)−F 10% 3−BB(F,F)CF2OB−CL 3% 一般式(2−2)で表される化合物として、 3−BB(F,F)CF2OBB−5 10% 5−BB(F,F)CF2OBB−2 5% 2−BB(F,F)CF2OBB−5 5% 5−BB(F,F)CF2OBB−3 4% 5−BB(F,F)CF2OBB−5 8% 一般式(3)で表される化合物として、 5−HBB(F)B−2 5% 5−HBB(F)B−3 5% 上記組成物の特性は、以下のようになった。 TNI = 96.2℃ T < −30℃ Δn = 0.185 Vth = 1.48V Δε = 15.0 VHR(25℃) = 98.6% VHR(100℃) = 95.0%Example 12 As a compound represented by the general formula (1) in the present invention, 3-BBB (F, F) -F 3% 3-BB2B (F, F) -F 10% 3-B2BB (F , F) -F 10% As a compound represented by the general formula (2-1), 2-BB (F, F) CF2OB (F, F) -F 2% 3-BB (F, F) CF2OB (F , F) -F 20% 5-BB (F, F) CF2OB (F, F) -F 10% 3-BB (F, F) CF2OB-CL 3% Compound represented by the general formula (2-2) 3-BB (F, F) CF2OBB-5 10% 5-BB (F, F) CF2OBB-2 5% 2-BB (F, F) CF2OBB-5 5% 5-BB (F, F) CF2OBB -34% 5-BB (F, F) CF2OBB-5 8% As a compound represented by the general formula (3), 5-HBB (F Characteristics of B-2 5% 5-HBB (F) B-3 5% above composition were as follows. T NI = 96.2 ℃ T C < -30 ℃ Δn = 0.185 Vth = 1.48V Δε = 15.0 VHR (25 ℃) = 98.6% VHR (100 ℃) = 95.0%

【0048】 実施例13 本発明における一般式(1)で表される化合物として、 3−BB2B(F,F)−F 15% 3−B2BB(F,F)−F 15% 一般式(2−1)で表される化合物として、 3−BB(F,F)CF2OB(F,F)−F 20% 一般式(2−2)で表される化合物として、 3−BB(F,F)CF2OBB−5 10% 5−BB(F,F)CF2OBB−2 5% 一般式(3)で表される化合物として、 5−HBB(F)B−2 10% 5−HBB(F)B−3 10% その他の成分として、 2−HBB(F)−F 3.5% 3−HBB(F)−F 4% 5−HBB(F)−F 7.5% 上記組成物の特性は、以下のようになった。 TNI = 111.4℃ T < −20℃ Δn = 0.186 Vth = 1.60V Δε = 13.2 VHR(25℃) = 98.4% VHR(100℃) = 94.7%Example 13 As a compound represented by the general formula (1) in the present invention, 3-BB2B (F, F) -F 15% 3-B2BB (F, F) -F 15% General formula (2- As a compound represented by 1), 3-BB (F, F) CF2OB (F, F) -F 20% As a compound represented by the general formula (2-2), 3-BB (F, F) CF2OBB -5 10% 5-BB (F, F) CF2OBB-2 5% As a compound represented by the general formula (3), 5-HBB (F) B-2 10% 5-HBB (F) B-3 10 % As other components, 2-HBB (F) -F 3.5% 3-HBB (F) -F 4% 5-HBB (F) -F 7.5% The characteristics of the composition are as follows. Became. T NI = 111.4 ℃ T C < -20 ℃ Δn = 0.186 Vth = 1.60V Δε = 13.2 VHR (25 ℃) = 98.4% VHR (100 ℃) = 94.7%

【0049】 実施例14 本発明における一般式(1)で表される化合物として、 3−BBB(F,F)−F 5% 3−BB2B(F,F)−F 15% 3−B2BB(F,F)−F 15% 一般式(2−1)で表される化合物として、 3−BB(F,F)CF2OB(F,F)−F 10% 一般式(2−2)で表される化合物として、 3−BB(F,F)CF2OBB−5 10% 5−BB(F,F)CF2OBB−2 5% 2−BB(F,F)CF2OBB−5 5% 5−BB(F,F)CF2OBB−3 5% 5−BB(F,F)CF2OBB−F 5% 5−BB(F,F)CF2OBB−5 5% 一般式(3)で表される化合物として、 5−HBB(F)B−2 10% 5−HBB(F)B−3 10% 上記組成物の特性は、以下のようになった。 TNI = 126.7℃ T < −20℃ Δn = 0.206 Vth = 1.75V Δε = 12.3 VHR(25℃) = 98.4% VHR(100℃) = 94.5%Example 14 As a compound represented by the general formula (1) in the present invention, 3-BBB (F, F) -F 5% 3-BB2B (F, F) -F 15% 3-B2BB (F , F) -F 15% As a compound represented by the general formula (2-1), 3-BB (F, F) CF2OB (F, F) -F 10% represented by the general formula (2-2) As the compound, 3-BB (F, F) CF2OBB-5 10% 5-BB (F, F) CF2OBB-2 5% 2-BB (F, F) CF2OBB-5 5% 5-BB (F, F) CF2OBB-3 5% 5-BB (F, F) CF2OBB-F 5% 5-BB (F, F) CF2OBB-5 5% As a compound represented by the general formula (3), 5-HBB (F) B -2 10% 5-HBB (F) B-3 10% The properties of the composition were as follows. T NI = 126.7 ℃ T C < -20 ℃ Δn = 0.206 Vth = 1.75V Δε = 12.3 VHR (25 ℃) = 98.4% VHR (100 ℃) = 94.5%

【0050】 実施例15 本発明における一般式(1)で表される化合物として、 3−BBB(F,F)−F 5% 3−BB2B(F,F)−F 10% 一般式(2−1)で表される化合物として、 3−BB(F,F)CF2OB(F,F)−F 20% 3−BB(F,F)CF2OB(F,F)−OCF3 10% 一般式(2−2)で表される化合物として、 3−BB(F,F)CF2OBB−5 5% 5−BB(F,F)CF2OBB−2 5% 2−BB(F,F)CF2OBB−5 5% 一般式(3)で表される化合物として、 5−HBB(F)B−2 10% 5−HBB(F)B−3 10% その他の成分として、 3−HBB(F,F)−F 20% 上記組成物の特性は、以下のようになった。 TNI = 107.6℃ T < −30℃ Δn = 0.181 Vth = 1.61V Δε = 14.1 VHR(25℃) = 98.5% VHR(100℃) = 95.5%Example 15 As a compound represented by the general formula (1) in the present invention, 3-BBB (F, F) -F 5% 3-BB2B (F, F) -F 10% The general formula (2- As the compound represented by 1), 3-BB (F, F) CF2OB (F, F) -F 20% 3-BB (F, F) CF2OB (F, F) -OCF3 10% General formula (2- As the compound represented by 2), 3-BB (F, F) CF2OBB-5 5% 5-BB (F, F) CF2OBB-2 5% 2-BB (F, F) CF2OBB-5 5% General formula As a compound represented by (3), 5-HBB (F) B-2 10% 5-HBB (F) B-3 10% As other components, 3-HBB (F, F) -F 20% The properties of the composition were as follows. T NI = 107.6 ℃ T C < -30 ℃ Δn = 0.181 Vth = 1.61V Δε = 14.1 VHR (25 ℃) = 98.5% VHR (100 ℃) = 95.5%

【0051】 実施例16 本発明における一般式(1)で表される化合物として、 3−BBB(F,F)−F 5% 3−BB2B(F,F)−F 10% 一般式(2−1)で表される化合物として、 3−BB(F,F)CF2OB(F,F)−F 20% 3−BB(F,F)CF2OB−OCF3 10% 一般式(2−2)で表される化合物として、 3−BB(F,F)CF2OBB−5 5% 5−BB(F,F)CF2OBB−2 5% 2−BB(F,F)CF2OBB−5 5% 一般式(3)で表される化合物として、 5−HBB(F)B−2 10% 5−HBB(F)B−3 10% その他の成分として、 3−HBB(F,F)−F 20% 上記組成物の特性は、以下のようになった。 TNI = 109.8℃ T < −30℃ Δn = 0.184 Vth = 1.66V Δε = 13.4 VHR(25℃) = 98.8% VHR(100℃) = 95.4%Example 16 As a compound represented by the general formula (1) in the present invention, 3-BBB (F, F) -F 5% 3-BB2B (F, F) -F 10% The general formula (2- As the compound represented by 1), 3-BB (F, F) CF2OB (F, F) -F 20% 3-BB (F, F) CF2OB-OCF3 10% represented by the general formula (2-2) As a compound, 3-BB (F, F) CF2OBB-5 5% 5-BB (F, F) CF2OBB-2 5% 2-BB (F, F) CF2OBB-5 5% Table represented by general formula (3) 5-HBB (F) B-2 10% as a compound to be used 5-HBB (F) B-3 10% As other components, 3-HBB (F, F) -F 20% It was as follows. T NI = 109.8 ℃ T C < -30 ℃ Δn = 0.184 Vth = 1.66V Δε = 13.4 VHR (25 ℃) = 98.8% VHR (100 ℃) = 95.4%

【0052】 実施例17 本発明における一般式(1)で表される化合物として、 3−BBB(F,F)−F 5% 3−BB2B(F,F)−F 10% 3−B2BB(F,F)−F 5% 一般式(2−1)で表される化合物として、 3−BB(F,F)CF2OB(F,F)−F 20% 3−BB(F,F)CF2OB(F,F)−CF3 5% 一般式(2−2)で表される化合物として、 3−BB(F,F)CF2OBB−5 5% 5−BB(F,F)CF2OBB−2 5% 2−BB(F,F)CF2OBB−5 5% 一般式(3)で表される化合物として、 5−HBB(F)B−2 10% 5−HBB(F)B−3 10% その他の成分として、 2−HBB(F)−F 5% 3−HBB(F)−F 5% 5−HBB(F)−F 10% 上記組成物の特性は、以下のようになった。 TNI = 108.5℃ T < −30℃ Δn = 0.183 Vth = 1.60V Δε = 14.3 VHR(25℃) = 98.8% VHR(100℃) = 95.1%Example 17 As a compound represented by the general formula (1) in the present invention, 3-BBB (F, F) -F 5% 3-BB2B (F, F) -F 10% 3-B2BB (F , F) -F 5% As a compound represented by the general formula (2-1), 3-BB (F, F) CF2OB (F, F) -F 20% 3-BB (F, F) CF2OB (F , F) -CF3 5% As a compound represented by the general formula (2-2), 3-BB (F, F) CF2OBB-5 5% 5-BB (F, F) CF2OBB-2 5% 2-BB (F, F) CF2OBB-5 5% As a compound represented by the general formula (3), 5-HBB (F) B-2 10% 5-HBB (F) B-3 10% -HBB (F) -F 5% 3-HBB (F) -F 5% 5-HBB (F) -F 10% It was as follows. T NI = 108.5 ℃ T C < -30 ℃ Δn = 0.183 Vth = 1.60V Δε = 14.3 VHR (25 ℃) = 98.8% VHR (100 ℃) = 95.1%

【0053】 実施例18 本発明における一般式(1)で表される化合物として、 3−BBB(F,F)−F 5% 3−BB2B(F,F)−F 10% 一般式(2−1)で表される化合物として、 3−BB(F,F)CF2OB(F,F)−F 20% 3−BB(F,F)CF2OB(F,F)−OCF3 10% 一般式(2−2)で表される化合物として、 3−BB(F,F)CF2OBB−5 5% 5−BB(F,F)CF2OBB−2 5% 2−BB(F,F)CF2OBB−5 5% 一般式(3)で表される化合物として、 5−HBB(F)B−2 10% 5−HBB(F)B−3 10% その他の成分として、 3−HBB(F,F)−F 10% 5−HBB(F,F)−F 10% 上記組成物の特性は、以下のようになった。 TNI = 114.4℃ T < −30℃ Δn = 0.187 Vth = 1.69V Δε = 12.1 VHR(25℃) = 98.7% VHR(100℃) = 95.3%Example 18 As a compound represented by the general formula (1) in the present invention, 3-BBB (F, F) -F 5% 3-BB2B (F, F) -F 10% The general formula (2- As the compound represented by 1), 3-BB (F, F) CF2OB (F, F) -F 20% 3-BB (F, F) CF2OB (F, F) -OCF3 10% General formula (2- As the compound represented by 2), 3-BB (F, F) CF2OBB-5 5% 5-BB (F, F) CF2OBB-2 5% 2-BB (F, F) CF2OBB-5 5% General formula As a compound represented by (3), 5-HBB (F) B-2 10% 5-HBB (F) B-3 10% As another component, 3-HBB (F, F) -F 10% 5 -HBB (F, F) -F 10% The characteristics of the composition were as follows. T NI = 114.4 ℃ T C < -30 ℃ Δn = 0.187 Vth = 1.69V Δε = 12.1 VHR (25 ℃) = 98.7% VHR (100 ℃) = 95.3%

【0054】 実施例19 本発明における一般式(1)で表される化合物として、 3−BBB(F,F)−F 5% 3−BB2B(F,F)−F 5% 3−B2BB(F,F)−F 5% 一般式(2−1)で表される化合物として、 3−BB(F,F)CF2OB(F,F)−F 20% 一般式(2−2)で表される化合物として、 3−BB(F,F)CF2OBB−5 5% 5−BB(F,F)CF2OBB−2 5% 2−BB(F,F)CF2OBB−5 5% 3−BB(F,F)CF2OBB(F,F)−F 5% 5−BB(F,F)CF2OBB(F,F)−F 5% 一般式(3)で表される化合物として、 5−HBB(F)B−2 10% 5−HBB(F)B−3 10% その他の成分として、 3−HBB(F,F)−F 20% 上記組成物の特性は、以下のようになった。 TNI = 113.9℃ T < −30℃ Δn = 0.188 Vth = 1.64V Δε = 12.7 VHR(25℃) = 98.4% VHR(100℃) = 94.5%Example 19 As a compound represented by the general formula (1) in the present invention, 3-BBB (F, F) -F 5% 3-BB2B (F, F) -F 5% 3-B2BB (F , F) -F 5% As a compound represented by the general formula (2-1), 3-BB (F, F) CF2OB (F, F) -F 20% represented by the general formula (2-2) As a compound, 3-BB (F, F) CF2OBB-5 5% 5-BB (F, F) CF2OBB-2 5% 2-BB (F, F) CF2OBB-5 5% 3-BB (F, F) CF2OBB (F, F) -F 5% 5-BB (F, F) CF2OBB (F, F) -F 5% As a compound represented by the general formula (3), 5-HBB (F) B-2 10 % 5-HBB (F) B-3 10% As other components, 3-HBB (F, F) -F 20% It became like. T NI = 113.9 ℃ T C < -30 ℃ Δn = 0.188 Vth = 1.64V Δε = 12.7 VHR (25 ℃) = 98.4% VHR (100 ℃) = 94.5%

【0055】 実施例20 本発明における一般式(1)で表される化合物として、 3−BBB(F,F)−F 5% 3−BB2B(F,F)−F 5% 3−B2BB(F,F)−F 5% 一般式(2−1)で表される化合物として、 3−BB(F,F)CF2OB(F,F)−F 20% 一般式(2−2)で表される化合物として、 3−BB(F,F)CF2OBB−5 5% 5−BB(F,F)CF2OBB−2 5% 2−BB(F,F)CF2OBB−5 5% 3−BB(F,F)CF2OBB(F)−OCF3 5% 5−BB(F,F)CF2OBB(F)−OCF3 5% 一般式(3)で表される化合物として、 5−HBB(F)B−2 10% 5−HBB(F)B−3 10% その他の成分として、 3−HBB(F,F)−F 20% 上記組成物の特性は、以下のようになった。 TNI = 115.4℃ T < −30℃ Δn = 0.189 Vth = 1.65V Δε = 12.8 VHR(25℃) = 98.5% VHR(100℃) = 94.9%Example 20 As a compound represented by the general formula (1) in the present invention, 3-BBB (F, F) -F 5% 3-BB2B (F, F) -F 5% 3-B2BB (F , F) -F 5% As a compound represented by the general formula (2-1), 3-BB (F, F) CF2OB (F, F) -F 20% represented by the general formula (2-2) As a compound, 3-BB (F, F) CF2OBB-5 5% 5-BB (F, F) CF2OBB-2 5% 2-BB (F, F) CF2OBB-5 5% 3-BB (F, F) CF2OBB (F) -OCF3 5% 5-BB (F, F) CF2OBB (F) -OCF3 5% As a compound represented by the general formula (3), 5-HBB (F) B-2 10% 5-HBB (F) B-3 10% As other component, 3-HBB (F, F) -F 20% Characteristics of the above composition , It was as follows. T NI = 115.4 ℃ T C < -30 ℃ Δn = 0.189 Vth = 1.65V Δε = 12.8 VHR (25 ℃) = 98.5% VHR (100 ℃) = 94.9%

【0056】 実施例21 本発明における一般式(1)で表される化合物として、 5−BBB(F,F)−F 5% 一般式(2−1)で表される化合物として、 3−BB(F,F)CF2OB(F,F)−F 20% 一般式(2−2)で表される化合物として、 3−BB(F,F)CF2OBB−5 8% 5−BB(F,F)CF2OBB−2 5% 5−BB(F,F)CF2OBB−3 3% 5−BB(F,F)CF2OBB−F 3% 一般式(3)で表される化合物として、 5−HBB(F)B−2 10% 5−HBB(F)B−3 10% その他の成分として、 3−HBB(F,F)−F 16% 2−HBB(F)−F 5% 3−HBB(F)−F 5% 5−HBB(F)−F 10% 上記組成物の特性は、以下のようになった。 TNI = 125.7℃ T < −30℃ Δn = 0.186 Vth = 1.97V Δε = 9.6 VHR(25℃) = 99.2% VHR(100℃) = 96.1%Example 21 As a compound represented by the general formula (1) in the present invention, 5-BBB (F, F) -F 5% As a compound represented by the general formula (2-1), 3-BB (F, F) CF2OB (F, F) -F 20% As a compound represented by the general formula (2-2), 3-BB (F, F) CF2OBB-5-8% 5-BB (F, F) CF2OBB-2 5% 5-BB (F, F) CF2OBB-3 3% 5-BB (F, F) CF2OBB-F 3% As a compound represented by the general formula (3), 5-HBB (F) B -2 10% 5-HBB (F) B-3 10% As other components, 3-HBB (F, F) -F 16% 2-HBB (F) -F 5% 3-HBB (F) -F 5% 5-HBB (F) -F 10% The properties of the composition were as follows. T NI = 125.7 ℃ T C < -30 ℃ Δn = 0.186 Vth = 1.97V Δε = 9.6 VHR (25 ℃) = 99.2% VHR (100 ℃) = 96.1%

【0057】 実施例22 本発明における一般式(1)で表される化合物として、 5−BBB(F,F)−F 5% 3−B2BB(F,F)−F 5% 一般式(2−1)で表される化合物として、 3−BB(F,F)CF2OB(F,F)−F 25% 一般式(2−2)で表される化合物として、 3−BB(F,F)CF2OBB−5 10% 5−BB(F,F)CF2OBB−2 5% 5−BB(F,F)CF2OBB−3 5% 5−BB(F,F)CF2OBB−F 5% 一般式(3)で表される化合物として、 5−HBB(F)B−2 10% 5−HBB(F)B−3 10% その他の成分として、 3−HBB(F,F)−F 5% 2−HBB(F)−F 3.5% 3−HBB(F)−F 4% 5−HBB(F)−F 7.5% 上記組成物の特性は、以下のようになった。 TNI = 122.3℃ T < −30℃ Δn = 0.194 Vth = 2.01V Δε = 10.2 VHR(25℃) = 98.9% VHR(100℃) = 95.5%Example 22 As a compound represented by the general formula (1) in the present invention, 5-BBB (F, F) -F 5% 3-B2BB (F, F) -F 5% The general formula (2- As a compound represented by 1), 3-BB (F, F) CF2OB (F, F) -F 25% As a compound represented by the general formula (2-2), 3-BB (F, F) CF2OBB -5 10% 5-BB (F, F) CF2OBB-2 5% 5-BB (F, F) CF2OBB-3 5% 5-BB (F, F) CF2OBB-F 5% Expressed by the general formula (3). 5-HBB (F) B-2 10% 5-HBB (F) B-3 10% As the other component, 3-HBB (F, F) -F 5% 2-HBB (F) -F 3.5% 3-HBB (F) -F 4% 5-HBB (F) -F 7.5% It became way. T NI = 122.3 ℃ T C < -30 ℃ Δn = 0.194 Vth = 2.01V Δε = 10.2 VHR (25 ℃) = 98.9% VHR (100 ℃) = 95.5%

【0058】 実施例23 本発明における一般式(1)で表される化合物として、 5−BBB(F,F)−F 5% 一般式(2−1)で表される化合物として、 3−BB(F,F)CF2OB(F,F)−F 20% 一般式(2−2)で表される化合物として、 3−BB(F,F)CF2OBB−5 5% 5−BB(F,F)CF2OBB−2 5% 5−BB(F,F)CF2OBB−3 5% 5−BB(F,F)CF2OBB−5 5% 一般式(3)で表される化合物として、 5−HBB(F)B−2 10% 5−HBB(F)B−3 10% その他の成分として、 3−HBB(F,F)−F 25% 5−HBB(F,F)−F 10% 上記組成物の特性は、以下のようになった。 TNI = 118.4℃ T < −30℃ Δn = 0.185 Vth = 1.75V Δε = 11.6 VHR(25℃) = 99.2% VHR(100℃) = 96.2%Example 23 As a compound represented by the general formula (1) in the present invention, 5-BBB (F, F) -F 5% As a compound represented by the general formula (2-1), 3-BB (F, F) CF2OB (F, F) -F 20% As a compound represented by the general formula (2-2), 3-BB (F, F) CF2OBB-5 5% 5-BB (F, F) CF2OBB-2 5% 5-BB (F, F) CF2OBB-3 5% 5-BB (F, F) CF2OBB-5 5% As a compound represented by the general formula (3), 5-HBB (F) B -2 10% 5-HBB (F) B-3 10% As other components, 3-HBB (F, F) -F 25% 5-HBB (F, F) -F 10% It was as follows. T NI = 118.4 ℃ T C < -30 ℃ Δn = 0.185 Vth = 1.75V Δε = 11.6 VHR (25 ℃) = 99.2% VHR (100 ℃) = 96.2%

【0059】 実施例24 本発明における一般式(1)で表される化合物として、 3−BBB(F,F)−F 3% 5−BBB(F,F)−F 5% 3−BB2B(F,F)−F 5% 3−B2BB(F,F)−F 5% 一般式(2−1)で表される化合物として、 3−BB(F,F)CF2OB(F,F)−F 23% 一般式(2−2)で表される化合物として、 3−BB(F,F)CF2OBB−5 8% 5−BB(F,F)CF2OBB−2 5% 5−BB(F,F)CF2OBB−3 5% 5−BB(F,F)CF2OBB−F 5% 5−BB(F,F)CF2OBB−5 10% 一般式(3)で表される化合物として、 5−HBB(F)B−2 8% 5−HBB(F)B−3 8% その他の成分として、 3−HBB(F,F)−F 10% 上記組成物の特性は、以下のようになった。 TNI = 117.9℃ T < −20℃ Δn = 0.194 Vth = 1.74V Δε = 11.6 VHR(25℃) = 98.8% VHR(100℃) = 95.4%Example 24 As a compound represented by the general formula (1) in the present invention, 3-BBB (F, F) -F 3% 5-BBB (F, F) -F 5% 3-BB2B (F , F) -F 5% 3-B2BB (F, F) -F 5% As a compound represented by the general formula (2-1), 3-BB (F, F) CF2OB (F, F) -F23 % As a compound represented by the general formula (2-2), 3-BB (F, F) CF2OBB-5 8% 5-BB (F, F) CF2OBB-2 5% 5-BB (F, F) CF2OBB -5% 5-BB (F, F) CF2OBB-F 5% 5-BB (F, F) CF2OBB-5 10% As a compound represented by the general formula (3), 5-HBB (F) B- 28% 5-HBB (F) B-3 8% As other components, 3-HBB (F, F) -F 10% It has become as follows. T NI = 117.9 ℃ T C < -20 ℃ Δn = 0.194 Vth = 1.74V Δε = 11.6 VHR (25 ℃) = 98.8% VHR (100 ℃) = 95.4%

【0060】 実施例25 本発明における一般式(1)で表される化合物として、 3−BBB(F,F)−F 5% 3−BB2B(F,F)−F 15% 3−B2BB(F,F)−F 15% 一般式(2−1)で表される化合物として、 3−BB(F,F)CF2OB(F,F)−F 20% 一般式(3)で表される化合物として、 5−HBB(F)B−2 10% 5−HBB(F)B−3 10% その他の成分として、 2−HBB(F)−F 6% 3−HBB(F)−F 6.5% 5−HBB(F)−F 12.5% 上記組成物の特性は、以下のようになった。 TNI = 98.9℃ T < −30℃ Δn = 0.169 Vth = 1.63V Δε = 12.8 VHR(25℃) = 98.6% VHR(100℃) = 95.1%Example 25 As a compound represented by the general formula (1) in the present invention, 3-BBB (F, F) -F 5% 3-BB2B (F, F) -F 15% 3-B2BB (F , F) -F 15% As a compound represented by the general formula (2-1), 3-BB (F, F) CF2OB (F, F) -F 20% As a compound represented by the general formula (3) 5-HBB (F) B-2 10% 5-HBB (F) B-3 10% As other components, 2-HBB (F) -F 6% 3-HBB (F) -F 6.5% 5-HBB (F) -F 12.5% The characteristics of the composition were as follows. T NI = 98.9 ℃ T C < -30 ℃ Δn = 0.169 Vth = 1.63V Δε = 12.8 VHR (25 ℃) = 98.6% VHR (100 ℃) = 95.1%

【0061】実施例26 本発明における一般式(1)で表される化合物として、 3−BBB(F,F)−F 5% 5−BBB(F,F)−F 5% 3−BB2B(F,F)−F 15% 3−B2BB(F,F)−F 15% 一般式(2−2)で表される化合物として、 3−BB(F,F)CF2OBB−5 10% 5−BB(F,F)CF2OBB−2 5% 2−BB(F,F)CF2OBB−5 5% 5−BB(F,F)CF2OBB−3 5% 5−BB(F,F)CF2OBB−F 5% 5−BB(F,F)CF2OBB−5 10% 一般式(3)で表される化合物として、 5−HBB(F)B−2 10% 5−HBB(F)B−3 10% 上記組成物の特性は、以下のようになった。 TNI = 143.0℃ T < −10℃ Δn = 0.218 Vth = 2.09V Δε = 9.6 VHR(25℃) = 98.3% VHR(100℃) = 94.7%Example 26 As a compound represented by the general formula (1) in the present invention, 3-BBB (F, F) -F 5% 5-BBB (F, F) -F 5% 3-BB2B (F , F) -F 15% 3-B2BB (F, F) -F 15% As a compound represented by the general formula (2-2), 3-BB (F, F) CF2OBB-5 10% 5-BB ( F, F) CF2OBB-2 5% 2-BB (F, F) CF2OBB-5 5% 5-BB (F, F) CF2OBB-3 5% 5-BB (F, F) CF2OBB-F 5% 5- BB (F, F) CF2OBB-5 10% As a compound represented by the general formula (3), 5-HBB (F) B-2 10% 5-HBB (F) B-3 10% Characteristics of the composition Was as follows: T NI = 143.0 ℃ T C < -10 ℃ Δn = 0.218 Vth = 2.09V Δε = 9.6 VHR (25 ℃) = 98.3% VHR (100 ℃) = 94.7%

【0062】 実施例27 本発明における一般式(1)で表される化合物として、 3−BBB(F,F)−F 5% 3−BB2B(F,F)−F 10% 3−B2BB(F,F)−F 10% 一般式(2−1)で表される化合物として、 3−BB(F,F)CF2OB(F,F)−F 30% 5−BB(F,F)CF2OB(F,F)−F 16% 3−BB(F,F)CF2OB(F)−F 5% 一般式(3)で表される化合物として、 5−HBB(F)B−2 12% 5−HBB(F)B−3 12% 上記組成物の特性は、以下のようになった。 TNI = 80.2℃ T < −30℃ Δn = 0.167 Vth = 1.27V Δε = 17.7 VHR(25℃) = 98.6% VHR(100℃) = 94.9%Example 27 As a compound represented by the general formula (1) in the present invention, 3-BBB (F, F) -F 5% 3-BB2B (F, F) -F 10% 3-B2BB (F , F) -F 10% As a compound represented by the general formula (2-1), 3-BB (F, F) CF2OB (F, F) -F 30% 5-BB (F, F) CF2OB (F , F) -F 16% 3-BB (F, F) CF2OB (F) -F 5% As a compound represented by the general formula (3), 5-HBB (F) B-2 12% 5-HBB ( F) B-3 12% The properties of the composition were as follows. T NI = 80.2 ℃ T C < -30 ℃ Δn = 0.167 Vth = 1.27V Δε = 17.7 VHR (25 ℃) = 98.6% VHR (100 ℃) = 94.9%

【0063】 実施例28 本発明における一般式(1)で表される化合物として、 3−BBB(F,F)−F 5% 5−BBB(F,F)−F 5% 3−BB2B(F,F)−F 5% 3−B2BB(F,F)−F 10% 一般式(2−1)で表される化合物として、 2−BB(F,F)CF2OB(F,F)−CF3 5% 3−BB(F,F)CF2OB(F,F)−CF3 10% 5−BB(F,F)CF2OB(F,F)−CF3 10% 一般式(2−2)で表される化合物として、 3−BB(F,F)CF2OBB−5 8% 5−BB(F,F)CF2OBB−2 5% 5−BB(F,F)CF2OBB−3 5% 5−BB(F,F)CF2OBB−F 5% 5−BB(F,F)CF2OBB−5 9% 一般式(3)で表される化合物として、 5−HBB(F)B−2 9% 5−HBB(F)B−3 9% 上記組成物の特性は、以下のようになった。 TNI = 120.3℃ T < −20℃ Δn = 0.206 Vth = 1.74V Δε = 11.9 VHR(25℃) = 98.7% VHR(100℃) = 95.0%Example 28 As the compound represented by the general formula (1) in the present invention, 3-BBB (F, F) -F 5% 5-BBB (F, F) -F 5% 3-BB2B (F , F) -F 5% 3-B2BB (F, F) -F 10% As a compound represented by the general formula (2-1), 2-BB (F, F) CF2OB (F, F) -CF35 % 3-BB (F, F) CF2OB (F, F) -CF3 10% 5-BB (F, F) CF2OB (F, F) -CF3 10% As a compound represented by the general formula (2-2) 3-BB (F, F) CF2OBB-5 8% 5-BB (F, F) CF2OBB-2 5% 5-BB (F, F) CF2OBB-3 5% 5-BB (F, F) CF2OBB- F 5% 5-BB (F, F) CF2OBB-5 9% As a compound represented by the general formula (3), 5-HBB (F) Characteristics of -2 9% 5-HBB (F) B-3 9% above composition were as follows. T NI = 120.3 ℃ T C < -20 ℃ Δn = 0.206 Vth = 1.74V Δε = 11.9 VHR (25 ℃) = 98.7% VHR (100 ℃) = 95.0%

【0064】 実施例29 本発明における一般式(1)で表される化合物として、 3−BBB(F,F)−F 5% 5−BBB(F,F)−F 5% 一般式(2−1)で表される化合物として、 3−BB(F,F)CF2OB(F,F)−F 15% 一般式(2−2)で表される化合物として、 3−BB(F,F)CF2OBB−5 5% 5−BB(F,F)CF2OBB−2 5% 5−BB(F,F)CF2OBB−3 3% 5−BB(F,F)CF2OBB−F 3% 5−BB(F,F)CF2OBB−5 3% 一般式(3)で表される化合物として、 5−HBB(F)B−2 10% 5−HBB(F)B−3 10% その他の成分として、 3−H2BB(F,F)−F 8% 3−H2HB(F,F)−F 5% 5−H2HB(F,F)−F 5% 2−HBB(F)−F 5% 3−HBB(F)−F 5% 5−HBB(F)−F 5% 3−HHB−CL 3% 上記組成物の特性は、以下のようになった。 TNI = 127.7℃ T < −30℃ Δn = 0.183 Vth = 2.04V Δε = 9.6 VHR(25℃) = 99.3% VHR(100℃) = 96.2%Example 29 As a compound represented by the general formula (1) in the present invention, 3-BBB (F, F) -F 5% 5-BBB (F, F) -F 5% The general formula (2- As a compound represented by 1), 3-BB (F, F) CF2OB (F, F) -F 15% As a compound represented by the general formula (2-2), 3-BB (F, F) CF2OBB -5 5% 5-BB (F, F) CF2OBB-2 5% 5-BB (F, F) CF2OBB-3 3% 5-BB (F, F) CF2OBB-F 3% 5-BB (F, F ) CF2OBB-5 3% As a compound represented by the general formula (3), 5-HBB (F) B-2 10% 5-HBB (F) B-3 10% As other components, 3-H2BB (F , F) -F 8% 3-H2HB (F, F) -F 5% 5-H2HB (F, F) -F 5% 2-HBB ( ) Characteristics of -F 5% 3-HBB (F) -F 5% 5-HBB (F) -F 5% 3-HHB-CL 3% above composition were as follows. T NI = 127.7 ℃ T C < -30 ℃ Δn = 0.183 Vth = 2.04V Δε = 9.6 VHR (25 ℃) = 99.3% VHR (100 ℃) = 96.2%

【0065】 実施例30 本発明における一般式(1)で表される化合物として、 3−BBB(F,F)−F 5% 3−B2BB(F,F)−F 5% 3−BB2B(F,F)−F 5% 一般式(2−1)で表される化合物として、 3−BB(F,F)CF2OB(F,F)−F 20% 一般式(2−2)で表される化合物として、 3−BB(F,F)CF2OBB−5 5% 5−BB(F,F)CF2OBB−2 5% 5−BB(F,F)CF2OBB−3 5% 5−BB(F,F)CF2OBB−F 5% 一般式(3)で表される化合物として、 5−HBB(F)B−2 10% 5−HBB(F)B−3 10% その他の成分として、 3−HBB(F,F)−F 5% 3−HHB(F,F)−F 7% 3−HH2B(F,F)−F 3% 2−HHB(F)−F 2.5% 3−HHB(F)−F 2.5% 5−HHB(F)−F 5% 上記組成物の特性は、以下のようになった。 TNI = 126.2℃ T < −30℃ Δn = 0.179 Vth = 2.02V Δε = 9.7 VHR(25℃) = 99.1% VHR(100℃) = 96.0%Example 30 As a compound represented by the general formula (1) in the present invention, 3-BBB (F, F) -F 5% 3-B2BB (F, F) -F 5% 3-BB2B (F , F) -F 5% As a compound represented by the general formula (2-1), 3-BB (F, F) CF2OB (F, F) -F 20% represented by the general formula (2-2) As a compound, 3-BB (F, F) CF2OBB-5 5% 5-BB (F, F) CF2OBB-2 5% 5-BB (F, F) CF2OBB-3 5% 5-BB (F, F) CF2OBB-F 5% As a compound represented by the general formula (3), 5-HBB (F) B-2 10% 5-HBB (F) B-3 10% As other components, 3-HBB (F, F) -F 5% 3-HHB (F, F) -F 7% 3-HH2B (F, F) -F 3% 2-HHB (F) -F2 0.5% 3-HHB (F) -F 2.5% 5-HHB (F) -F 5% The characteristics of the composition were as follows. T NI = 126.2 ℃ T C < -30 ℃ Δn = 0.179 Vth = 2.02V Δε = 9.7 VHR (25 ℃) = 99.1% VHR (100 ℃) = 96.0%

【0066】 実施例31 本発明における一般式(1)で表される化合物として、 3−BBB(F,F)−F 5% 5−BBB(F,F)−F 5% 一般式(2−1)で表される化合物として、 3−BB(F,F)CF2OB(F,F)−F 20% 一般式(2−2)で表される化合物として、 3−BB(F,F)CF2OBB−5 8% 5−BB(F,F)CF2OBB−2 5% 5−BB(F,F)CF2OBB−3 3% 5−BB(F,F)CF2OBB−F 3% 5−BB(F,F)CF2OBB−5 3% 一般式(3)で表される化合物として、 5−HBB(F)B−2 10% 5−HBB(F)B−3 10% その他の成分として、 3−H2BB(F,F)−F 5% 2−HBB(F)−F 5% 3−HBB(F)−F 5% 5−HBB(F)−F 5% 3−HH−4 3% 3−HB−O2 5% 上記組成物の特性は、以下のようになった。 TNI = 125.7℃ T < −30℃ Δn = 0.186 Vth = 1.93V Δε = 9.3 VHR(25℃) = 99.2% VHR(100℃) = 96.2%Example 31 As the compound represented by the general formula (1) in the present invention, 3-BBB (F, F) -F 5% 5-BBB (F, F) -F 5% The general formula (2- As a compound represented by 1), 3-BB (F, F) CF2OB (F, F) -F 20% As a compound represented by the general formula (2-2), 3-BB (F, F) CF2OBB -5 8% 5-BB (F, F) CF2OBB-2 5% 5-BB (F, F) CF2OBB-3 3% 5-BB (F, F) CF2OBB-F 3% 5-BB (F, F ) CF2OBB-5 3% As a compound represented by the general formula (3), 5-HBB (F) B-2 10% 5-HBB (F) B-3 10% As other components, 3-H2BB (F , F) -F 5% 2-HBB (F) -F 5% 3-HBB (F) -F 5% 5-HBB (F) -F Characteristics of% 3-HH-4 3% 3-HB-O2 5% above composition were as follows. T NI = 125.7 ℃ T C < -30 ℃ Δn = 0.186 Vth = 1.93V Δε = 9.3 VHR (25 ℃) = 99.2% VHR (100 ℃) = 96.2%

【0067】[0067]

【発明の効果】本発明の液晶組成物は、アクティブ・マ
トリックス方式の液晶表示素子(AM−LCD)に求め
られる一般的な特性を満たしながら、適当なしきい値電
圧を持ち、特に、高温領域において電圧保持率の高い、
屈折率異方性Δnの大きい液晶組成物で、AM−LCD
表示素子にも好適に使用される。また、本発明の液晶組
成物を用いて構成される液晶表示素子は、低い駆動電圧
と高い応答速度を有する液晶表示素子である。
The liquid crystal composition of the present invention has an appropriate threshold voltage while satisfying the general characteristics required for an active matrix type liquid crystal display device (AM-LCD), and particularly, in a high temperature region. High voltage holding ratio,
AM-LCD is a liquid crystal composition having a large refractive index anisotropy Δn.
It is also suitably used for display elements. Further, a liquid crystal display device formed using the liquid crystal composition of the present invention is a liquid crystal display device having a low driving voltage and a high response speed.

───────────────────────────────────────────────────── 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) C09K 19/44 C09K 19/44 G02F 1/13 500 G02F 1/13 500 (72)発明者 村城 勝之 千葉県市原市五井海岸5番地の1 チッソ 石油化学株式会社機能材料研究所内 Fターム(参考) 4H027 BA01 BC04 BD04 BD05 BD07 BD08 BE05 CE04 CE05 CG04 CH04 CH05 CM01 CN04 CQ04 CR04 CT04 CU01 CU05 CW01──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. 7 Identification symbol FI Theme coat ゛ (Reference) C09K 19/44 C09K 19/44 G02F 1/13 500 G02F 1/13 500 5F, Goi Kaigan, Ichihara, Ichihara, Japan F-term (reference) 4H027 BA01 BC04 BD04 BD05 BD07 BD08 BE05 CE04 CE05 CG04 CH04 CH05 CM01 CN04 CQ04 CR04 CT04 CU01 CU05 CW01

Claims (5)

【特許請求の範囲】[Claims] 【請求項1】一般式(1)で表される化合物からなる第
一成分および一般式(2−1)および(2−2)からな
る群から選ばれた少なくとも一種の化合物からなる第二
成分を含有する液晶組成物。 (式中、Rは炭素数1〜10のアルキル基を表し、R
2、R3はそれぞれ独立に炭素数1〜10のアルキル基、
アルコキシ基、炭素数2〜10のアルコキシメチル基、
アルケニル基を表し、Z1、Z2はそれぞれ独立に-C2
4-または単結合を表し、XおよびXはそれぞれ独立
にF、Cl、CF3、OCF3、OCF2H、炭素数1〜
10のアルキル基、アルコキシ基、アルコキシメチル
基、炭素数2〜10のアルケニル基を表し、Y1、Y2
3、Y4、Y5、Y6、Y7、Y8、Y9およびY10はそれ
ぞれ独立にHもしくはFを表わす。)。
1. A first component comprising a compound represented by the general formula (1) and a second component comprising at least one compound selected from the group consisting of the general formulas (2-1) and (2-2). A liquid crystal composition containing (Wherein, R 1 represents an alkyl group having 1 to 10 carbon atoms;
2 and R 3 are each independently an alkyl group having 1 to 10 carbon atoms;
An alkoxy group, an alkoxymethyl group having 2 to 10 carbon atoms,
Represents an alkenyl group, and Z 1 and Z 2 are each independently —C 2 H
4 - or a single bond, X 1 and X 2 are F each independently, Cl, CF 3, OCF 3 , OCF 2 H, 1~ carbon atoms
Represents an alkyl group, an alkoxy group, an alkoxymethyl group, an alkenyl group having 2 to 10 carbon atoms, Y 1 , Y 2 ,
Y 3, Y 4, represent Y 5, Y 6, Y 7 , Y 8, Y 9 and Y 10 each independently H or F. ).
【請求項2】さらに、一般式(3)で表される化合物か
ら選ばれた少なくとも一種の化合物からなる第三成分を
含有する請求項1記載の液晶組成物。 (式中、R4、R5はそれぞれ独立に炭素数1〜10のア
ルキル基、アルコキシ基炭素数2〜10のアルコキシメ
チル基もしくはアルケニル基を表し、Aは側位のHが
Fで置換されていてもよい1,4−フェニレン基を表
し、Aはトランス−1,4−シクロヘキシレン基もし
くは1,4−フェニレン基を表わす。)。
2. The liquid crystal composition according to claim 1, further comprising a third component comprising at least one compound selected from the compounds represented by the general formula (3). (Wherein, R 4 and R 5 each independently represent an alkyl group having 1 to 10 carbon atoms, an alkoxy group, an alkoxymethyl group or an alkenyl group having 2 to 10 carbon atoms, and A 1 is a group wherein H at the side is substituted with F. And A 2 represents a trans-1,4-cyclohexylene group or a 1,4-phenylene group.
【請求項3】液晶組成物の全重量に対して、第一成分を
3〜50重量%、第二成分を3〜90重量%および第三
成分を3〜40重量%含有する請求項2記載の液晶組成
物。
3. The liquid crystal composition according to claim 2, comprising 3 to 50% by weight of the first component, 3 to 90% by weight of the second component and 3 to 40% by weight of the third component, based on the total weight of the liquid crystal composition. Liquid crystal composition.
【請求項4】第二成分が、一般式(2−1―a)および
(2−2―a)からなる群から選ばれた少なくとも一種
の化合物である請求項3記載の液晶組成物。 (式中、R2、R3はそれぞれ独立に炭素数1〜10のア
ルキル基、アルコキシ基、炭素数2〜10のアルケニル
基を表し、XおよびXはそれぞれ独立にF、Cl、
CF3、OCF3、炭素数1〜10のアルキル基、アルコ
キシ基もしくは炭素数2〜10のアルケニル基を表し、
3、Y4、Y5、Y6、Y9およびY10はそれぞれ独立に
HまたはFを表わす。)。
4. The liquid crystal composition according to claim 3, wherein the second component is at least one compound selected from the group consisting of general formulas (2-1-a) and (2-2-a). (Wherein, R 2 and R 3 each independently represent an alkyl group having 1 to 10 carbon atoms, an alkoxy group, or an alkenyl group having 2 to 10 carbon atoms, and X 1 and X 2 each independently represent F, Cl,
CF 3 , OCF 3 , an alkyl group having 1 to 10 carbon atoms, an alkoxy group or an alkenyl group having 2 to 10 carbon atoms,
Y 3 , Y 4 , Y 5 , Y 6 , Y 9 and Y 10 each independently represent H or F. ).
【請求項5】請求項1〜4のいずれか1項記載の液晶組
成物を用いて構成される液晶表示素子。
5. A liquid crystal display device comprising the liquid crystal composition according to claim 1.
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004315819A (en) * 2003-04-11 2004-11-11 Merck Patent Gmbh Liquid crystal medium
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JP2008156642A (en) * 2006-12-20 2008-07-10 Merck Patent Gmbh Liquid crystal medium and liquid crystal display
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WO2009028368A1 (en) * 2007-08-30 2009-03-05 Chisso Corporation Liquid crystal composition, and liquid crystal display element
EP2377909A1 (en) 2010-04-17 2011-10-19 Merck Patent GmbH Liquid crystalline compounds and liquid crystalline media
WO2012081516A1 (en) * 2010-12-14 2012-06-21 Jnc株式会社 Liquid crystal composition and liquid crystal display element
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CN107922841A (en) * 2015-08-26 2018-04-17 默克专利股份有限公司 Liquid crystal media

Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09241643A (en) * 1996-03-07 1997-09-16 Chisso Corp Liquid crystal composition and liquid crystal display element
JP2000087040A (en) * 1998-09-10 2000-03-28 Chisso Corp Liquid crystal composition and liquid crystal display element
JP2000256307A (en) * 1999-03-09 2000-09-19 Chisso Corp Thioether compound, liquid crystal composition and liquid crystal display element having negative value of permittivity anisotropy
JP2001003051A (en) * 1999-04-19 2001-01-09 Chisso Corp Liquid crystal composition and liquid crystal display element
JP2001003053A (en) * 1999-04-19 2001-01-09 Chisso Corp Liquid crystal composition and liquid crystal display element
JP2001011448A (en) * 1999-05-04 2001-01-16 Merck Patent Gmbh Stn liquid crystal display
JP2001011449A (en) * 1999-05-04 2001-01-16 Merck Patent Gmbh Stn liquid crystal display
JP2001031685A (en) * 1999-07-15 2001-02-06 Chisso Corp Silicone compound, liquid crystal composition and liquid crystal displaying element
JP2001064651A (en) * 1999-06-30 2001-03-13 Merck Patent Gmbh Tn and stn liquid crystal displays
JP2001072626A (en) * 1999-06-29 2001-03-21 Chisso Corp New liquid crystalline compound having negative dielectric anisotropy value, liquid crystal composition and liquid crystal display element
JP2001123170A (en) * 1999-10-25 2001-05-08 Chisso Corp Liquid crystal composition and liquid crystal display element
JP2003327964A (en) * 2001-04-27 2003-11-19 Chisso Corp Liquid crystal composition and liquid crystal display element

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09241643A (en) * 1996-03-07 1997-09-16 Chisso Corp Liquid crystal composition and liquid crystal display element
JP2000087040A (en) * 1998-09-10 2000-03-28 Chisso Corp Liquid crystal composition and liquid crystal display element
JP2000256307A (en) * 1999-03-09 2000-09-19 Chisso Corp Thioether compound, liquid crystal composition and liquid crystal display element having negative value of permittivity anisotropy
JP2001003051A (en) * 1999-04-19 2001-01-09 Chisso Corp Liquid crystal composition and liquid crystal display element
JP2001003053A (en) * 1999-04-19 2001-01-09 Chisso Corp Liquid crystal composition and liquid crystal display element
JP2001011448A (en) * 1999-05-04 2001-01-16 Merck Patent Gmbh Stn liquid crystal display
JP2001011449A (en) * 1999-05-04 2001-01-16 Merck Patent Gmbh Stn liquid crystal display
JP2001072626A (en) * 1999-06-29 2001-03-21 Chisso Corp New liquid crystalline compound having negative dielectric anisotropy value, liquid crystal composition and liquid crystal display element
JP2001064651A (en) * 1999-06-30 2001-03-13 Merck Patent Gmbh Tn and stn liquid crystal displays
JP2001031685A (en) * 1999-07-15 2001-02-06 Chisso Corp Silicone compound, liquid crystal composition and liquid crystal displaying element
JP2001123170A (en) * 1999-10-25 2001-05-08 Chisso Corp Liquid crystal composition and liquid crystal display element
JP2003327964A (en) * 2001-04-27 2003-11-19 Chisso Corp Liquid crystal composition and liquid crystal display element

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004315819A (en) * 2003-04-11 2004-11-11 Merck Patent Gmbh Liquid crystal medium
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JP2006249425A (en) * 2005-02-25 2006-09-21 Merck Patent Gmbh Liquid-crystalline medium
JP2008156642A (en) * 2006-12-20 2008-07-10 Merck Patent Gmbh Liquid crystal medium and liquid crystal display
US8133410B2 (en) 2007-08-27 2012-03-13 Jnc Corporation Liquid crystal composition and liquid crystal display device
WO2009028367A1 (en) * 2007-08-27 2009-03-05 Chisso Corporation Liquid crystal composition, and liquid crystal display element
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TWI547474B (en) * 2010-04-17 2016-09-01 馬克專利公司 Liquid-crystalline compounds and liquid-crystalline media
US8551359B2 (en) 2010-04-17 2013-10-08 Merck Patent Gmbh Liquid-crystalline compounds and liquid-crystalline media
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CN102329198B (en) * 2010-04-17 2015-08-05 默克专利股份有限公司 Liquid crystalline cpd and liquid crystal media
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WO2014125911A1 (en) 2013-02-13 2014-08-21 Jnc株式会社 Liquid-crystalline compound having difluoromethyleneoxy group, liquid crystal composition, and liquid crystal display element
US9657229B2 (en) 2013-02-13 2017-05-23 Jnc Corporation Liquid crystal compound having difluoromethyleneoxy, liquid crystal composition and liquid crystal display device
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