JP2006037053A - Nematic liquid crystal composition and liquid crystal display element using the same - Google Patents
Nematic liquid crystal composition and liquid crystal display element using the same Download PDFInfo
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本発明は電気光学的液晶表示材料として有用な誘電率異方性Δεが負の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。 The present invention relates to a nematic liquid crystal composition having a negative dielectric anisotropy Δε useful as an electro-optical liquid crystal display material, and a liquid crystal display device using the same.
液晶表示素子は、時計、電卓をはじめとして、家庭用各種電気機器、測定機器、自動車用パネル、ワープロ、電子手帳、プリンター、コンピューター、テレビ等に用いられるようになっている。液晶表示方式としては、その代表的なものにTN(捩れネマチック)型、STN(超捩れネマチック)型、DS(動的光散乱)型、GH(ゲスト・ホスト)型、IPS(インプレーンスイッチング)型、OCB(光学補償複屈折)型、ECB(電圧制御複屈折)型、VA(垂直配向)型、CSH(カラースーパーホメオトロピック)型、あるいはFLC(強誘電性液晶)等を挙げることができる。また駆動方式としても従来のスタティック駆動からマルチプレックス駆動が一般的になり、単純マトリックス方式、最近ではTFT(薄膜トランジスタ)やTFD(薄膜ダイオード)等により駆動されるアクティブマトリックス(AM)方式が主流となっている。 The liquid crystal display element is used in various electric appliances for home use, measuring instruments, automobile panels, word processors, electronic notebooks, printers, computers, televisions, etc., including clocks and calculators. Typical liquid crystal display methods include TN (twisted nematic), STN (super twisted nematic), DS (dynamic light scattering), GH (guest / host), and IPS (in-plane switching). Type, OCB (optical compensation birefringence) type, ECB (voltage controlled birefringence) type, VA (vertical alignment) type, CSH (color super homeotropic) type, FLC (ferroelectric liquid crystal), etc. . As a driving method, multiplex driving is generally used instead of conventional static driving, and the active matrix (AM) method driven by a TFT (thin film transistor), TFD (thin film diode) or the like has become mainstream recently. ing.
これらの表示方式において、IPS型、ECB型、VA型、あるいはCSH型等は現在汎用のTN型やSTN型と異なり、誘電率異方性(Δε)が負の液晶材料を用いるという特徴を有する。これらの中で特にAM駆動によるVA型表示は、高速で広視野角の要求される表示素子、例えばテレビ等への応用において、現在最も期待されているものである。 In these display systems, the IPS type, ECB type, VA type, CSH type and the like have a feature that a liquid crystal material having a negative dielectric anisotropy (Δε) is used, unlike currently-used TN type and STN type. . Among these, VA type display by AM driving is currently most expected in application to a display element that requires a high speed and a wide viewing angle, such as a television.
VA型等の表示方式に用いられる液晶材料には、低電圧駆動、高速応答、広い動作温度範囲が要求される。すなわち、誘電率異方性が負で絶対値が大きく、低粘度であり、高いネマチック相−等方性液体相転移温度(Tni)が要求されている。また、屈折率異方性(Δn)とセルギャップ(d)との積であるΔn×dの設定から、液晶材料の屈折率異方性をセルギャップに合わせて適当な範囲に調節する必要がある。液晶表示素子をテレビ等へ応用する場合においては高速応答性が重視されるため、粘度の低い液晶材料が要求される。 A liquid crystal material used in a display method such as a VA type is required to have low voltage driving, high speed response, and a wide operating temperature range. That is, the dielectric anisotropy is negative, the absolute value is large, the viscosity is low, and a high nematic phase-isotropic liquid phase transition temperature (Tni) is required. In addition, it is necessary to adjust the refractive index anisotropy of the liquid crystal material to an appropriate range according to the cell gap from the setting of Δn × d, which is the product of the refractive index anisotropy (Δn) and the cell gap (d). is there. In the case of applying a liquid crystal display element to a television or the like, since high-speed response is important, a liquid crystal material having a low viscosity is required.
誘電率異方性が負の液晶材料として、以下のような2,3-ジフルオロフェニレン骨格を有する液晶化合物(特許文献1参照)が開示されている。 As a liquid crystal material having a negative dielectric anisotropy, a liquid crystal compound having the following 2,3-difluorophenylene skeleton (see Patent Document 1) is disclosed.
(式中、R及びR'は炭素数1から10のアルキル基又はアルコキシ基を表す。)
しかし、これらの化合物を用いた誘電率異方性が負の液晶組成物は、液晶テレビ等の高速応答が要求される液晶組成物においては十分に低い粘性を実現するに至っていない。
(In the formula, R and R ′ represent an alkyl group having 1 to 10 carbon atoms or an alkoxy group.)
However, a liquid crystal composition having a negative dielectric anisotropy using these compounds has not yet achieved a sufficiently low viscosity in a liquid crystal composition that requires a high-speed response such as a liquid crystal television.
一方、本願発明の一般式(I)で表される化合物はすでに開示されている(特許文献2及び特許文献3参照)が、これらの化合物と他にどのような化合物を用いることで液晶組成物の粘性を低減できるかについての具体的な開示は無い。 On the other hand, although the compound represented by the general formula (I) of the present invention has already been disclosed (see Patent Document 2 and Patent Document 3), a liquid crystal composition can be obtained by using any of these compounds and other compounds. There is no specific disclosure as to whether the viscosity of can be reduced.
また、本願発明の一般式(I)で表される化合物を用いた液晶組成物は既に開示されている(特許文献4および特許文献5参照)に開示されているが、具体的にどの様な化合物と組み合わせることにより粘性を低減できるかについての具体的な開示は無い。
従って、誘電率異方性が負の液晶組成物で粘度の低い液晶組成物の開発が望まれていた。
Further, a liquid crystal composition using the compound represented by the general formula (I) of the present invention has already been disclosed (see Patent Document 4 and Patent Document 5). There is no specific disclosure as to whether viscosity can be reduced by combining with a compound.
Accordingly, development of a liquid crystal composition having a negative dielectric anisotropy and a low viscosity has been desired.
本発明が解決しようとする課題は、絶対値の大きな負の誘電率異方性を持ち、屈折率異方性を低減させるか又は上昇させることなく粘度の低い液晶組成物を提供し、さらにそれを用いたVA型等の液晶表示素子を提供することにある。 The problem to be solved by the present invention is to provide a liquid crystal composition having a negative dielectric anisotropy having a large absolute value, and having a low viscosity without reducing or increasing the refractive index anisotropy. Another object is to provide a VA type liquid crystal display element using the above.
本発明は、上記課題を解決するために鋭意検討した結果、
第一成分として、一般式(I)
The present invention, as a result of intensive studies to solve the above problems,
As the first component, the general formula (I)
(式中、R1は炭素数1から10のアルキル基又は炭素数2から10のアルケニル基を表し、これらの基中に存在する1個のCH2基又は隣接していない2個以上のCH2基はO及び/又はSに置換されてもよく、またこれらの基中に存在する1個又は2個以上の水素原子はF又はClに置換されてもよく、R2は炭素数1から10のアルキル基、炭素数1から10のアルコキシル基、炭素数2から10のアルケニル基又は炭素数3から10のアルケニルオキシ基を表し、
mは0、1又は2を表す。)
で表される化合物を1種又は2種以上含有し、
第二成分として、一般式(II)
(In the formula, R 1 represents an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and one CH 2 group present in these groups or two or more non-adjacent CHs. Two groups may be substituted with O and / or S, and one or more hydrogen atoms present in these groups may be substituted with F or Cl, and R 2 has 1 to Represents an alkyl group having 10 carbon atoms, an alkoxyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 3 to 10 carbon atoms,
m represents 0, 1 or 2. )
Containing one or more compounds represented by:
As the second component, the general formula (II)
R3又はR4の少なくともどちらか一方はアルケニル基であり、
At least one of R 3 and R 4 is an alkenyl group,
B1及びB2はそれぞれ独立的に
(a) トランス-1,4-シクロへキシレン基(この基中に存在する1個のCH2基又は隣接していない2個のCH2基は酸素原子又は硫黄原子に置換されてもよい)
(b) 1,4-フェニレン基(この基中に存在する1個又は2個以上のCH基は窒素原子に置換されてもよい)
(c) 1,4-シクロヘキセニレン基、1,4-ビシクロ[2.2.2]オクチレン基、ピペリジン-1,4-ジイル基、ナフタレン-2,6-ジイル基、デカヒドロナフタレン-2,6-ジイル基及び1,2,3,4-テトラヒドロナフタレン-2,6-ジイル基
からなる群より選ばれる基を表し、上記の基(a)、基(b)又は基(c)はCN又はハロゲンで置換されていてもよく、
Y1及びY2はそれぞれ独立的に
-CH2CH2-、-CH=CH-、-CH(CH3)CH2-、-CH2CH(CH3)-、-CH(CH3)CH(CH3)-、-CF2CF2-、-CF=CF-、-CH2O-、-OCH2-、-OCH(CH3)-、-CH(CH3)O-、-(CH2)4-、-(CH2)3O-、-O(CH2)3-、-C≡C-、-CF2O-、-OCF2-、-COO-、-OCO-、-COS-、-SCO-又は単結合を表し、
Y2及びB2が複数存在する場合は、それらは同一でもよく異なっていてもよく、
pは0、1又は2を表す。)
で表される化合物を1種又は2種以上含有する誘電率異方性が負の液晶組成物を提供し、
さらに、当該液晶組成物を用いた液晶表示素子を提供する。
B 1 and B 2 are each independently
(a) trans-1,4-cyclohexylene group (two CH 2 groups not one CH 2 group or adjacent present in this group may be substituted with an oxygen atom or a sulfur atom)
(b) 1,4-phenylene group (one or more CH groups present in this group may be substituted with a nitrogen atom)
(c) 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1,4-diyl group, naphthalene-2,6-diyl group, decahydronaphthalene-2,6 Represents a group selected from the group consisting of a -diyl group and a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and the group (a), the group (b) or the group (c) is CN or May be substituted with halogen,
Y 1 and Y 2 are independently
-CH 2 CH 2- , -CH = CH-, -CH (CH 3 ) CH 2- , -CH 2 CH (CH 3 )-, -CH (CH 3 ) CH (CH 3 )-, -CF 2 CF 2- , -CF = CF-, -CH 2 O-, -OCH 2- , -OCH (CH 3 )-, -CH (CH 3 ) O-,-(CH 2 ) 4 -,-(CH 2 ) 3 O -, - O (CH 2) 3 -, - C≡C -, - CF 2 O -, - OCF 2 -, - COO -, - OCO -, - COS -, - SCO- or a single bond ,
When there are a plurality of Y 2 and B 2 , they may be the same or different,
p represents 0, 1 or 2. )
A liquid crystal composition having a negative dielectric anisotropy containing one or more of the compounds represented by:
Furthermore, a liquid crystal display element using the liquid crystal composition is provided.
本発明の液晶化合物の組み合わせによって、屈折率異方性をほぼ維持したまま、粘度の低い誘電率異方性が負の液晶組成物が得られた。この組成物を用いることにより、高温域まで高い電圧保持率を維持できる信頼性に優れた液晶表示素子が提供され、このディスプレイはVA方式やECB方式、IPS方式等の液晶ディスプレイとして非常に実用的であり、特にセルギャップを薄くすることなく高速応答化に有効である。 By the combination of the liquid crystal compounds of the present invention, a liquid crystal composition having a low viscosity and a negative dielectric anisotropy was obtained while substantially maintaining the refractive index anisotropy. By using this composition, a highly reliable liquid crystal display element capable of maintaining a high voltage holding ratio up to a high temperature range is provided, and this display is very practical as a liquid crystal display of VA mode, ECB mode, IPS mode, etc. In particular, it is effective for high-speed response without reducing the cell gap.
本願発明における液晶組成物において、第一成分として一般式(I)で表される化合物を1種又は2種以上を含有するが、1種から20種が好ましく、1種から15種がより好ましく、1種から10種がさらに好ましく、1種から8種が特に好ましい。 In the liquid crystal composition of the present invention, the first component contains one or more compounds represented by the general formula (I), preferably 1 to 20 types, more preferably 1 to 15 types. 1 to 10 types are more preferable, and 1 to 8 types are particularly preferable.
一般式(I)で表される化合物は、絶対値の大きな負の誘電率異方性を有するが、含有量が多いと粘度を上昇させる傾向がある、又はスメクチック−ネマチック相転移温度を上昇させてしまうことがあるため、低い粘度を重視する場合、あるいは低いスメクチック−ネマチック相転移温度を重視する場合はこれらの含有率が少ないことが好ましく、絶対値の大きな負の誘電率異方性を重視する場合はこれらの含有率が多いことが好ましい。 The compound represented by the general formula (I) has a negative dielectric anisotropy having a large absolute value, but if the content is large, the compound tends to increase the viscosity, or increase the smectic-nematic phase transition temperature. Therefore, when low viscosity is important or when low smectic-nematic phase transition temperature is important, it is preferable that these contents are small, and negative dielectric anisotropy with a large absolute value is important. When doing so, it is preferable that these content rates are large.
一般式(I)において、R1は炭素数1から10のアルキル基又は炭素数2から10のアルケニル基、炭素数1から5のアルコキシル基によって置換された炭素数1から7のアルキル基又は炭素数1から5のアルコキシル基によって置換された炭素数2から7のアルケニル基を表すことが好ましく、炭素数1から10のアルキル基又は炭素数2から10のアルケニル基を表すことがより好ましく、炭素数1から10のアルキル基を表すことがさらに好ましく、R2は炭素数1から10のアルキル基、アルコキシル基、炭素数2から10のアルケニル基又は炭素数3から10のアルケニルオキシ基を表すことが好ましく、炭素数1から10のアルキル基又はアルコキシル基を表すことがより好ましく、炭素数1から10のアルコキシル基を表すことがさらに好ましく、mは0又は1を表すことが好ましい。 In general formula (I), R 1 is an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkyl group having 1 to 7 carbon atoms substituted by an alkoxyl group having 1 to 5 carbon atoms. It preferably represents an alkenyl group having 2 to 7 carbon atoms substituted by an alkoxyl group having 1 to 5 carbon atoms, and more preferably represents an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms. More preferably, it represents an alkyl group having 1 to 10 carbon atoms, and R 2 represents an alkyl group having 1 to 10 carbon atoms, an alkoxyl group, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 3 to 10 carbon atoms. It is more preferable that it represents an alkyl group or alkoxyl group having 1 to 10 carbon atoms, more preferably an alkoxyl group having 1 to 10 carbon atoms, and m preferably represents 0 or 1.
さらに詳述すると、一般式(I)は、具体的な構造として以下の一般式(I-A)及び一般式(I-B)で表される化合物が好ましい。 More specifically, the general formula (I) is preferably a compound represented by the following general formula (I-A) or general formula (I-B) as a specific structure.
(式中、R5、R6、R7、及びR8は、一般式(I)におけるR1と同じ意味を表す。)
第二成分として、一般式(II)で表される化合物を1種又は2種以上を含有するが、1種から12種が好ましく、1種から8種がより好ましく、1種から6種がさらに好ましい。
(In the formula, R 5 , R 6 , R 7 and R 8 represent the same meaning as R 1 in the general formula (I).)
As the second component, one or more compounds represented by the general formula (II) are contained, preferably 1 to 12 types, more preferably 1 to 8 types, and more preferably 1 to 6 types. Further preferred.
一般式(II)で表される化合物は、誘電率異方性の絶対値を大きくする効果はほとんどないものの粘度を低くする効果があり、低い粘度を重視する場合はこれらの含有率が多いことが好ましく、誘電率異方性の絶対値を大きくすることを重視する場合はこれらの含有率が少ないことが好ましい。 The compound represented by the general formula (II) has the effect of lowering the viscosity although there is almost no effect of increasing the absolute value of the dielectric anisotropy, and when the low viscosity is regarded as important, these contents are large. When the importance of increasing the absolute value of the dielectric anisotropy is important, it is preferable that the content of these elements is small.
一般式(II)において、R3及びR4はそれぞれ独立的に、炭素数1から10のアルキル基、炭素数2から10のアルケニル基、炭素数1から10のアルコキシル基又は炭素数3から10のアルケニルオキシ基を表すことが好ましく、R3又はR4の少なくともどちらか一方は炭素数2から10のアルケニル基または炭素数3から10のアルケニルオキシ基を表すことがより好ましく、
具体的にはR3又はR4の少なくともどちらか一方は、-CH=CH2、-CH=CHCH3(E体)、-(CH2)2CH=CH2、-(CH2)2CH=CHCH3(E体)、-(CH2)4CH=CH2、-(CH2)4CH=CHCH3(E体)又は-(CH2)6CH=CH2を表すことがさらに好ましい。
In general formula (II), R 3 and R 4 are each independently an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkoxyl group having 1 to 10 carbon atoms, or 3 to 10 carbon atoms. It is preferable that at least one of R 3 and R 4 represents an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 10 carbon atoms,
Specifically, at least one of R 3 and R 4 is —CH═CH 2 , —CH═CHCH 3 (E-form), — (CH 2 ) 2 CH═CH 2 , — (CH 2 ) 2 CH = CHCH 3 (E form),-(CH 2 ) 4 CH = CH 2 ,-(CH 2 ) 4 CH = CHCH 3 (E form) or-(CH 2 ) 6 CH = CH 2 is more preferable. .
B1及びB2はそれぞれ独立的に、トランス-1,4-シクロヘキシレン基(この基中に存在する1個のCH2基又は隣接していない2個のCH2基が酸素原子に置換されているものを含む)、1,4-フェニレン基(この基中に存在する1個又は2個以上のCH基は窒素原子に置換されているものを含む)、1,4-シクロヘキセニレン基、1,4-ビシクロ[2.2.2]オクチレン基、ピペリジン-1,4-ジイル基、ナフタレン-2,6-ジイル基、デカヒドロナフタレン-2,6-ジイル基又は1,2,3,4-テトラヒドロナフタレン-2,6-ジイル基もしくはこれらの水素原子がフッ素原子で置換された置換基を表すことが好ましく、トランス-1,4-シクロヘキシレン基、1,4-フェニレン基、フッ素置換された1,4-フェニレン基又は1,4-ビシクロ[2.2.2]オクチレン基がより好ましい。 B 1 and B 2 are each independently a trans-1,4-cyclohexylene group (one CH 2 group present in this group or two non-adjacent CH 2 groups are substituted with oxygen atoms). 1,4-phenylene group (including one or more CH groups substituted by nitrogen atoms), 1,4-cyclohexenylene group 1,4-bicyclo [2.2.2] octylene group, piperidine-1,4-diyl group, naphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group, or 1,2,3,4 -It preferably represents a tetrahydronaphthalene-2,6-diyl group or a substituent in which these hydrogen atoms are substituted with fluorine atoms, trans-1,4-cyclohexylene group, 1,4-phenylene group, fluorine-substituted A 1,4-phenylene group or a 1,4-bicyclo [2.2.2] octylene group is more preferable.
Y1及びY2はそれぞれ独立的に、-CH2CH2-、-CH=CH-(E体)、-CH(CH3)CH2-、-CH2CH(CH3)-、-CH(CH3)CH(CH3)-、-CF2CF2-、-CF=CF-(E体)、-CH2O-、-OCH2-、-OCH(CH3)-、-CH(CH3)O-、-(CH2)4-、-(CH2)3O-、-O(CH2)3-、-C≡C-、-CF2O-、-OCF2-、-COO-、-OCO-、-COS-、-SCO-又は単結合を表すことが好ましいが、-CH2CH2-、-CH=CH-(E体)、-CH(CH3)CH2-、-CH2CH(CH3)-、-CF2CF2-、-CF=CF-(E体)、-CH2O-、-OCH2-、-OCH(CH3)-、-CH(CH3)O-、-C≡C-、-CF2O-、-OCF2-又は単結合がより好ましく、-CH2CH2-、-CH=CH-(E体)又は単結合がさらに好ましい。 Y 1 and Y 2 are each independently -CH 2 CH 2- , -CH = CH- (E form), -CH (CH 3 ) CH 2- , -CH 2 CH (CH 3 )-, -CH (CH 3 ) CH (CH 3 )-, -CF 2 CF 2- , -CF = CF- (E form), -CH 2 O-, -OCH 2- , -OCH (CH 3 )-, -CH ( CH 3 ) O-,-(CH 2 ) 4 -,-(CH 2 ) 3 O-, -O (CH 2 ) 3- , -C≡C-, -CF 2 O-, -OCF 2 -,- COO-, -OCO-, -COS-, -SCO- or a single bond is preferred, but -CH 2 CH 2- , -CH = CH- (E form), -CH (CH 3 ) CH 2- , -CH 2 CH (CH 3 )-, -CF 2 CF 2- , -CF = CF- (E form), -CH 2 O-, -OCH 2- , -OCH (CH 3 )-, -CH ( CH 3 ) O—, —C≡C—, —CF 2 O—, —OCF 2 — or a single bond is more preferable, and —CH 2 CH 2 —, —CH═CH— (E form) or a single bond is further preferable.
さらに詳述すると、一般式(II)は、具体的な構造として以下の一般式(II-A-1)から一般式(II-A-8)からなる群で表される化合物が好ましい。 More specifically, the general formula (II) is preferably a compound represented by the group consisting of the following general formula (II-A-1) to general formula (II-A-8) as a specific structure.
(式中、R9、R10およびR11は、-CH3、-CH2CH3、-(CH2)2CH3、-(CH2)3CH3、-(CH2)4CH3、-(CH2)5CH3、-(CH2)6CH3、-(CH2)7CH3、-OCH3、-OCH2CH3、-O(CH2)2CH3、-O(CH2)3CH3、-O(CH2)4CH3、-O(CH2)5CH3、-O(CH2)6CH3または-O(CH2)7CH3を表す。)
また、一般式(II)は、具体的な構造として以下の一般式(II-B-1)から一般式(II-B-14)からなる群で表される化合物も好ましい。
(Where R 9 , R 10 and R 11 are —CH 3 , —CH 2 CH 3 , — (CH 2 ) 2 CH 3 , — (CH 2 ) 3 CH 3 , — (CH 2 ) 4 CH 3 ,-(CH 2 ) 5 CH 3 ,-(CH 2 ) 6 CH 3 ,-(CH 2 ) 7 CH 3 , -OCH 3 , -OCH 2 CH 3 , -O (CH 2 ) 2 CH 3 , -O (CH 2 ) 3 CH 3 , —O (CH 2 ) 4 CH 3 , —O (CH 2 ) 5 CH 3 , —O (CH 2 ) 6 CH 3 or —O (CH 2 ) 7 CH 3 is represented. )
Further, the general formula (II) is also preferably a compound represented by the following general formula (II-B-1) to general formula (II-B-14) as a specific structure.
(式中、R12、R13、R14、R15、R16、R17、R18、R19及びR20は、-CH3、-CH2CH3、-(CH2)2CH3、-(CH2)3CH3、-(CH2)4CH3、-(CH2)5CH3、-(CH2)6CH3、-(CH2)7CH3、-OCH3、-OCH2CH3、-O(CH2)2CH3、-O(CH2)3CH3、-O(CH2)4CH3、-O(CH2)5CH3、-O(CH2)6CH3または-O(CH2)7CH3を表す。)
また、一般式(II)は、具体的な構造として以下の一般式(II-C-1)から一般式(II-C-14)からなる群で表される化合物も好ましい。
(Wherein R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 and R 20 are —CH 3 , —CH 2 CH 3 , — (CH 2 ) 2 CH 3 ,-(CH 2 ) 3 CH 3 ,-(CH 2 ) 4 CH 3 ,-(CH 2 ) 5 CH 3 ,-(CH 2 ) 6 CH 3 ,-(CH 2 ) 7 CH 3 , -OCH 3 , -OCH 2 CH 3 , -O (CH 2 ) 2 CH 3 , -O (CH 2 ) 3 CH 3 , -O (CH 2 ) 4 CH 3 , -O (CH 2 ) 5 CH 3 , -O (CH 2) represents a 6 CH 3 or -O (CH 2) 7 CH 3 .)
Further, the general formula (II) is also preferably a compound represented by the following general formula (II-C-1) to general formula (II-C-14) as a specific structure.
(式中、R21、R22、R23及びR24は、-CH3、-CH2CH3、-(CH2)2CH3、-(CH2)3CH3、-(CH2)4CH3、-(CH2)5CH3、-(CH2)6CH3、-(CH2)7CH3、-OCH3、-OCH2CH3、-O(CH2)2CH3、-O(CH2)3CH3、-O(CH2)4CH3、-O(CH2)5CH3、-O(CH2)6CH3または-O(CH2)7CH3を表す。)
また、一般式(II)は、具体的な構造として以下の一般式(II-D-1)から一般式(II-D-14)からなる群で表される化合物も好ましい。
(Wherein R 21 , R 22 , R 23 and R 24 are —CH 3 , —CH 2 CH 3 , — (CH 2 ) 2 CH 3 , — (CH 2 ) 3 CH 3 , — (CH 2 ) 4 CH 3 ,-(CH 2 ) 5 CH 3 ,-(CH 2 ) 6 CH 3 ,-(CH 2 ) 7 CH 3 , -OCH 3 , -OCH 2 CH 3 , -O (CH 2 ) 2 CH 3 , -O (CH 2 ) 3 CH 3 , -O (CH 2 ) 4 CH 3 , -O (CH 2 ) 5 CH 3 , -O (CH 2 ) 6 CH 3 or -O (CH 2 ) 7 CH 3 Represents.)
Further, the general formula (II) is also preferably a compound represented by the following general formula (II-D-1) to general formula (II-D-14) as a specific structure.
(式中、R25、R26、R27及びR28は、-CH3、-CH2CH3、-(CH2)2CH3、-(CH2)3CH3、-(CH2)4CH3、-(CH2)5CH3、-(CH2)6CH3、-(CH2)7CH3、-OCH3、-OCH2CH3、-O(CH2)2CH3、-O(CH2)3CH3、-O(CH2)4CH3、-O(CH2)5CH3、-O(CH2)6CH3または-O(CH2)7CH3を表す。)
本発明のネマチック液晶組成物は、一般式(I-A)および一般式(I-B)からなる化合物群から選ばれる1種または2種以上の化合物を20から90質量%含有し、かつ、一般式(II-A-1)から一般式(II-A-8)からなる化合物群から選ばれる1種または2種以上の化合物、または/および、一般式(II-B-1)から一般式(II-B-14)からなる化合物群から選ばれる1種または2種以上の化合物、または/および、一般式(II-C-1)から一般式(II-C-14)からなる化合物群から選ばれる1種または2種以上の化合物、または/および、一般式(II-D-1)から一般式(II-D-14)からなる化合物群から選ばれる1種または2種以上の化合物を10から60質量%含有することが好ましい。
(In the formula, R 25 , R 26 , R 27 and R 28 are —CH 3 , —CH 2 CH 3 , — (CH 2 ) 2 CH 3 , — (CH 2 ) 3 CH 3 , — (CH 2 ) 4 CH 3 ,-(CH 2 ) 5 CH 3 ,-(CH 2 ) 6 CH 3 ,-(CH 2 ) 7 CH 3 , -OCH 3 , -OCH 2 CH 3 , -O (CH 2 ) 2 CH 3 , -O (CH 2 ) 3 CH 3 , -O (CH 2 ) 4 CH 3 , -O (CH 2 ) 5 CH 3 , -O (CH 2 ) 6 CH 3 or -O (CH 2 ) 7 CH 3 Represents.)
The nematic liquid crystal composition of the present invention contains 20 to 90% by mass of one or more compounds selected from the compound group consisting of the general formula (IA) and the general formula (IB), and the general formula (II -A-1) to one or more compounds selected from the group consisting of general formula (II-A-8), and / or general formula (II-B-1) to general formula (II- B-14) selected from the compound group consisting of one or more compounds selected from the group consisting of compounds, and / or the compound group consisting of formulas (II-C-1) to (II-C-14) 1 or 2 or more compounds, and / or 1 or 2 or more compounds selected from the compound group consisting of general formula (II-D-1) to general formula (II-D-14) from 10 It is preferable to contain 60 mass%.
一般式(I-A)および一般式(I-B)からなる化合物群から選ばれる1種または2種以上の化合物を30から80質量%含有することがより好ましく、35から70質量%含有することがさらに好ましい。 The content of one or more compounds selected from the group consisting of the general formula (IA) and the general formula (IB) is more preferably 30 to 80% by mass, and further preferably 35 to 70% by mass. .
一般式(II-A-1)から一般式(II-A-8)からなる化合物群から選ばれる1種または2種以上の化合物、または/および、一般式(II-B-1)から一般式(II-B-14)からなる化合物群から選ばれる1種または2種以上の化合物、または/および、一般式(II-C-1)から一般式(II-C-14)からなる化合物群から選ばれる1種または2種以上の化合物、または/および、一般式(II-D-1)から一般式(II-D-14)からなる化合物群から選ばれる1種または2種以上の化合物を20から60質量%含有することがより好ましく、30から50質量%含有することがさらに好ましい。 One or more compounds selected from the group consisting of general formula (II-A-1) to general formula (II-A-8), or / and general formula (II-B-1) to general One or more compounds selected from the group consisting of compounds of formula (II-B-14) or / and compounds of formula (II-C-14) to formula (II-C-14) One or more compounds selected from the group, and / or one or more compounds selected from the group consisting of compounds of general formula (II-D-1) to general formula (II-D-14) The content of the compound is more preferably 20 to 60% by mass, and further preferably 30 to 50% by mass.
追加の成分として、一般式(III-A)から(III-H)からなる化合物群から選ばれる1種又は2種以上の化合物を含有することも好ましい。 As an additional component, it is also preferable to contain one or more compounds selected from the compound group consisting of general formulas (III-A) to (III-H).
上記ネマチック液晶組成物は、液晶表示素子に有用であり、特にアクティブマトリクス駆動用液晶表示素子に有用であり、VAモード、IPSモード又はECBモード用液晶表示素子に用いることができる。 The nematic liquid crystal composition is useful for a liquid crystal display element, particularly useful for an active matrix driving liquid crystal display element, and can be used for a VA mode, IPS mode or ECB mode liquid crystal display element.
本発明のネマテチック液晶組成物は、上記の化合物以外に、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もよい。 The nematic liquid crystal composition of the present invention may contain a normal nematic liquid crystal, a smectic liquid crystal, a cholesteric liquid crystal and the like in addition to the above compounds.
以下に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『質量%』を意味する。 EXAMPLES The present invention will be described in further detail with reference to examples below, but the present invention is not limited to these examples. Further, “%” in the compositions of the following Examples and Comparative Examples means “% by mass”.
実施例中、測定した特性は以下の通りである。
TNI :ネマチック―等方相転移温度(℃)
Δn :25℃における複屈折率
Δε :25℃における誘電率異方性
η :粘度(mPa・s) (20℃)
(実施例1)
以下の構造で表される液晶組成物を調整しその物性値を測定した。
In the examples, the measured characteristics are as follows.
T NI : Nematic-isotropic phase transition temperature (° C)
Δn: Birefringence at 25 ° C. Δε: Dielectric anisotropy at 25 ° C. η: Viscosity (mPa · s) (20 ° C.)
Example 1
A liquid crystal composition represented by the following structure was prepared and measured for physical properties.
(比較例1)
比較例1として一般式(I)を含まない以下の構造で表される液晶組成物を調整しその物性値を測定した。
(Comparative Example 1)
As Comparative Example 1, a liquid crystal composition represented by the following structure not containing the general formula (I) was prepared, and its physical property values were measured.
実施例1は、比較例1よりも小さいΔnと、絶対値が大きな負のΔε、および低い粘度を有することがわかる。
It can be seen that Example 1 has a smaller Δn than that of Comparative Example 1, a negative Δε having a large absolute value, and a low viscosity.
(実施例2)
以下の構造で表される液晶組成物を調整しその物性値を測定した。
(Example 2)
A liquid crystal composition represented by the following structure was prepared and measured for physical properties.
(比較例2)
比較例2として一般式(I)の含有量が実施例2よりも少なく、一般式(II)を含まない以下の構造で表される液晶組成物を調整しその物性値を測定した。
(Comparative Example 2)
As Comparative Example 2, a liquid crystal composition represented by the following structure containing less general formula (I) than that of Example 2 and not containing general formula (II) was prepared and measured for physical properties.
実施例2は、比較例2よりも絶対値が大きな負のΔεを有しているにもかかわらず、Δn、Tniが比較例2とほぼ同等であり、低い粘度を有していることがわかる。
Although Example 2 has negative Δε having a larger absolute value than Comparative Example 2, Δn and Tni are almost the same as Comparative Example 2 and have a low viscosity. .
(実施例3)
以下の構造で表される液晶組成物を調整しその物性値を測定した。
(Example 3)
A liquid crystal composition represented by the following structure was prepared and measured for physical properties.
(実施例4)
以下の構造で表される液晶組成物を調整しその物性値を測定した。
Example 4
A liquid crystal composition represented by the following structure was prepared and measured for physical properties.
(実施例5)
以下の構造で表される液晶組成物を調整しその物性値を測定した。
(Example 5)
A liquid crystal composition represented by the following structure was prepared and measured for physical properties.
(実施例6)
以下の構造で表される液晶組成物を調整しその物性値を測定した。
(Example 6)
A liquid crystal composition represented by the following structure was prepared and measured for physical properties.
実施例6の特性は、Tni:84.5℃、Δn:0.084、Δε:-4.5、η:18.7mPa・sであった。
The characteristics of Example 6 were Tni: 84.5 ° C., Δn: 0.084, Δε: −4.5, and η: 18.7 mPa · s.
Claims (11)
mは0、1又は2を表す。)
で表される化合物を1種又は2種以上含有し、
第二成分として、一般式(II)
B1及びB2はそれぞれ独立的に
(a) トランス-1,4-シクロへキシレン基(この基中に存在する1個のCH2基又は隣接していない2個のCH2基は酸素原子又は硫黄原子に置換されてもよい)
(b) 1,4-フェニレン基(この基中に存在する1個又は2個以上のCH基は窒素原子に置換されてもよい)
(c) 1,4-シクロヘキセニレン基、1,4-ビシクロ[2.2.2]オクチレン基、ピペリジン-1,4-ジイル基、ナフタレン-2,6-ジイル基、デカヒドロナフタレン-2,6-ジイル基及び1,2,3,4-テトラヒドロナフタレン-2,6-ジイル基
からなる群より選ばれる基を表し、上記の基(a)、基(b)又は基(c)はCN又はハロゲンで置換されていてもよく、
Y1及びY2はそれぞれ独立的に
-CH2CH2-、-CH=CH-、-CH(CH3)CH2-、-CH2CH(CH3)-、-CH(CH3)CH(CH3)-、-CF2CF2-、-CF=CF-、-CH2O-、-OCH2-、-OCH(CH3)-、-CH(CH3)O-、-(CH2)4-、-(CH2)3O-、-O(CH2)3-、-C≡C-、-CF2O-、-OCF2-、-COO-、-OCO-、-COS-、-SCO-又は単結合を表し、
Y2及びB2が複数存在する場合は、それらは同一でもよく異なっていてもよく、
pは0、1又は2を表す。)
で表される化合物を1種又は2種以上含有する、
誘電率異方性が負のネマチック液晶組成物。 As the first component, the general formula (I)
m represents 0, 1 or 2. )
Containing one or more compounds represented by:
As the second component, the general formula (II)
B 1 and B 2 are each independently
(a) trans-1,4-cyclohexylene group (two CH 2 groups not one CH 2 group or adjacent present in this group may be substituted with an oxygen atom or a sulfur atom)
(b) 1,4-phenylene group (one or more CH groups present in this group may be substituted with a nitrogen atom)
(c) 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1,4-diyl group, naphthalene-2,6-diyl group, decahydronaphthalene-2,6 Represents a group selected from the group consisting of a -diyl group and a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and the group (a), the group (b) or the group (c) is CN or May be substituted with halogen,
Y 1 and Y 2 are independently
-CH 2 CH 2- , -CH = CH-, -CH (CH 3 ) CH 2- , -CH 2 CH (CH 3 )-, -CH (CH 3 ) CH (CH 3 )-, -CF 2 CF 2- , -CF = CF-, -CH 2 O-, -OCH 2- , -OCH (CH 3 )-, -CH (CH 3 ) O-,-(CH 2 ) 4 -,-(CH 2 ) 3 O -, - O (CH 2) 3 -, - C≡C -, - CF 2 O -, - OCF 2 -, - COO -, - OCO -, - COS -, - SCO- or a single bond ,
When there are a plurality of Y 2 and B 2 , they may be the same or different,
p represents 0, 1 or 2. )
Containing one or more compounds represented by:
A nematic liquid crystal composition having a negative dielectric anisotropy.
で表される化合物群から選ばれる1種又は2種以上の化合物を含有する、請求項1記載のネマチック液晶組成物。 General formula (IA) and general formula (IB)
The nematic liquid crystal composition of Claim 1 containing the 1 type, or 2 or more types of compound chosen from the compound group represented by these.
(式中、R9、R10及びR11は、それぞれ独立して炭素数1から10のアルキル基を表し、これらの基中に存在する1個のCH2基又は隣接していない2個以上のCH2基はO及び/又はSに置換されてもよく、またこれらの基中に存在する1個又は2個以上の水素原子はF又はClに置換されてもよい。)で表される化合物群から選ばれる1種又は2種以上の化合物を含有する請求項1又は2記載のネマチック液晶組成物。 From general formula (II-A-1) to general formula (II-A-8)
(Wherein R 9 , R 10 and R 11 each independently represents an alkyl group having 1 to 10 carbon atoms, one CH 2 group present in these groups or two or more not adjacent to each other) The CH 2 group in the above may be substituted with O and / or S, and one or more hydrogen atoms present in these groups may be substituted with F or Cl. The nematic liquid crystal composition of Claim 1 or 2 containing the 1 type, or 2 or more types of compound chosen from a compound group.
A liquid crystal display element for VA mode, IPS mode or ECB mode using the nematic liquid crystal composition according to claim 1.
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH04154645A (en) * | 1990-10-16 | 1992-05-27 | Asahi Glass Co Ltd | Production of crystallized glass |
US5384065A (en) * | 1990-09-04 | 1995-01-24 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Matrix liquid-crystal display |
JP2000096055A (en) * | 1998-09-12 | 2000-04-04 | Merck Patent Gmbh | Nematic liquid crystal composition and liquid crystal display containing the composition |
-
2004
- 2004-07-30 JP JP2004223492A patent/JP4802463B2/en active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5384065A (en) * | 1990-09-04 | 1995-01-24 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Matrix liquid-crystal display |
JPH04154645A (en) * | 1990-10-16 | 1992-05-27 | Asahi Glass Co Ltd | Production of crystallized glass |
JP2000096055A (en) * | 1998-09-12 | 2000-04-04 | Merck Patent Gmbh | Nematic liquid crystal composition and liquid crystal display containing the composition |
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