JP2007091796A - Nematic liquid crystal composition - Google Patents
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- 239000000203 mixture Substances 0.000 title claims abstract description 48
- 239000004988 Nematic liquid crystal Substances 0.000 title claims abstract description 22
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 62
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 239000011159 matrix material Substances 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 230000007704 transition Effects 0.000 claims description 14
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000005407 trans-1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])[C@]([H])([*:2])C([H])([H])C([H])([H])[C@@]1([H])[*:1] 0.000 claims description 10
- -1 naphthalene-2,6-diyl Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000013078 crystal Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000012071 phase Substances 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 13
- 239000007791 liquid phase Substances 0.000 description 7
- 239000004990 Smectic liquid crystal Substances 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 4
- 239000007790 solid phase Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 3
- 125000005653 3,5-difluoro-1,4-phenylene group Chemical group [H]C1=C(F)C([*:2])=C(F)C([H])=C1[*:1] 0.000 description 2
- 125000005451 3-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:1])C([H])=C(F)C([*:2])=C1[H] 0.000 description 2
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical class C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- CFFHCMKGIPEENO-UHFFFAOYSA-N CC(CC1)Cc2c1c(F)c(C)c(F)c2 Chemical compound CC(CC1)Cc2c1c(F)c(C)c(F)c2 CFFHCMKGIPEENO-UHFFFAOYSA-N 0.000 description 1
- RPMUDXVQHUECRE-UHFFFAOYSA-N CC1COC(C)OC1 Chemical compound CC1COC(C)OC1 RPMUDXVQHUECRE-UHFFFAOYSA-N 0.000 description 1
- HBXFIXSFKULBOG-UHFFFAOYSA-N Cc1cc(F)c(C)c(F)c1 Chemical compound Cc1cc(F)c(C)c(F)c1 HBXFIXSFKULBOG-UHFFFAOYSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3004—Cy-Cy
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Abstract
Description
本発明は電気光学的液晶表示材料として有用なネマチック晶組成物、これを用いた液晶表示装置に関する。 The present invention relates to a nematic crystal composition useful as an electro-optical liquid crystal display material, and a liquid crystal display device using the same.
表示品質が優れていることから、アクティブマトリクス形液晶表示装置が携帯端末、液晶テレビ、プロジェクタ、コンピューター等の市場に出されている。アクティブマトリクス表示方式は、画素毎にTFT(薄膜トランジスタ)あるいはMIM(メタル・インシュレータ・メタル)等が使われており、この方式には高電圧保持率であることが重要視されている。また、更に広い視角特性を得るためにIPS、OCBモードと組み合わせたTFT表示やより明るい表示を得るためにECBモードの反射型が提案されている。この様な表示素子に対応するために、現在も新しい液晶化合物あるいは液晶組成物の提案がなされている(特許文献1、特許文献2)。 Due to the excellent display quality, active matrix liquid crystal display devices are put on the market for portable terminals, liquid crystal televisions, projectors, computers and the like. In the active matrix display method, TFT (thin film transistor) or MIM (metal insulator metal) is used for each pixel, and high voltage holding ratio is regarded as important in this method. Also, in order to obtain a wider viewing angle characteristic, a TFT display combined with IPS and OCB modes and a reflection type of ECB mode have been proposed to obtain a brighter display. In order to cope with such display elements, new liquid crystal compounds or liquid crystal compositions have been proposed (Patent Document 1 and Patent Document 2).
ツイステッドネマチック液晶表示素子(TN-LCD)やスーパーツイステッドネマチック液晶表示素子(STN-LCD)においては、液晶の屈折率異方性(Δn)と液晶媒体の厚さ(d)との積であるリターデーション(R;R=Δn・d)をある一定値(TN-LCDでは0.4〜0.45に設定する場合が多い。)に設定する。 In twisted nematic liquid crystal display elements (TN-LCD) and super twisted nematic liquid crystal display elements (STN-LCD), the retarder is the product of the refractive index anisotropy (Δn) of the liquid crystal and the thickness (d) of the liquid crystal medium. The foundation (R; R = Δn · d) is set to a certain value (0.4 to 0.45 is often set for TN-LCD).
反射型または半透過型LCDでは、光が液晶媒体に入射し、背面の反射板で反射して再度液晶媒体中を通過するため、透過型LCDと比較して実質の光路長が2倍になるため、同じリターデーション値にするためには、液晶媒体のΔnを半分程度に小さくする必要がある。 In a reflective or transflective LCD, light enters the liquid crystal medium, reflects off the back reflector, and passes through the liquid crystal medium again, so the actual optical path length is doubled compared to the transmissive LCD. Therefore, in order to obtain the same retardation value, it is necessary to reduce Δn of the liquid crystal medium to about half.
低Δn液晶組成物は、Δn値の小さいシクロヘキサン環のみで構成されたビシクロヘキサン誘導体等の含有率を大きくすることで得ることができる。しかし、これらの化合物は一般的にΔεが大きくなく、低電圧化が困難であった。 A low Δn liquid crystal composition can be obtained by increasing the content of a bicyclohexane derivative composed only of a cyclohexane ring having a small Δn value. However, these compounds generally have a large Δε, and it has been difficult to reduce the voltage.
Δnが小さく、低電圧駆動が可能なΔεを大きくする手法としてフェニルシクロヘキシルジオキサン化合物を用いた液晶組成物が提案されている(特許文献3、4)。しかし、これらの例ではエステル化合物を使用しており、長期間の動作において不良が発生しやすい等の問題点を抱えており、信頼性に優れた液晶組成物は提供されていなかった。 A liquid crystal composition using a phenylcyclohexyldioxane compound has been proposed as a method of increasing Δε that is small in Δn and can be driven at a low voltage (Patent Documents 3 and 4). However, in these examples, ester compounds are used, and there are problems such that defects are likely to occur during long-term operation, and a liquid crystal composition having excellent reliability has not been provided.
一方、ビシクロヘキサン誘導体とフェニルシクロヘキシルジオキサン化合物を組み合わせた屈折率異方性の小さい液晶組成物も既に知られており、好ましい化合物の具体例が開示されている(特許文献5)。しかしながら、この組成物は液晶相の温度範囲が狭いため実用的な液晶組成物としては使用することができないものである。 On the other hand, a liquid crystal composition having a small refractive index anisotropy in which a bicyclohexane derivative and a phenylcyclohexyldioxane compound are combined is already known, and a specific example of a preferable compound is disclosed (Patent Document 5). However, since this composition has a narrow liquid crystal phase temperature range, it cannot be used as a practical liquid crystal composition.
以上のことから、液晶相温度範囲が広く、Δnが小さく、Δεが大きく、粘性が低く、かつ信頼性に優れた液晶組成物を得ることは困難であった。 From the above, it has been difficult to obtain a liquid crystal composition having a wide liquid crystal phase temperature range, a small Δn, a large Δε, a low viscosity, and excellent reliability.
本発明が解決しようとする課題は、液晶相温度範囲が広く、Δnが小さく、Δεが大きく、粘性が低く、かつ信頼性に優れたアクティブマトリクス型液晶表示素子用液晶組成物を提供すること、また、この液晶組成物を使用した動作温度範囲が広いアクティブマトリクス型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 for an active matrix liquid crystal display device having a wide liquid crystal phase temperature range, a small Δn, a large Δε, a low viscosity, and excellent reliability. It is another object of the present invention to provide an active matrix liquid crystal display element using this liquid crystal composition and having a wide operating temperature range.
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(1)、 As a result of intensive studies to solve the above problems, the present invention has the general formula (1) as the first component,
環Aは
(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個以上のCH2基は -O- 及び又は -S- に置き換えられてもよい)
(b) 1,4-フェニレン基(この基中に存在する1個のCH2基又は隣接していない2個以上のCH2基は -N- に置き換えられてもよい)
からなる群より選ばれる基であり、上記の基(a)、基(b)はCH3又はハロゲンで置換されていても良く、
Z1はそれぞれ独立的には、-CH2O-、-OCH2-、-CF2O-、-OCF2-、-CH2CH2-、-CF2CF2-、-CH=CH-、-(CH2)4-、-CH=CH-CH2CH2-、-CH2CH2-CH=CH- 又は単結合であり、
Q1は-OCH2-、-OCF2-、-OCHF-、-CF2-、または単結合であり、
X1〜X3はそれぞれ独立してH、F又はClである。)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ことを特徴とするアクティブマトリクス型液晶表示素子用液晶組成物及び当該液晶組成物を構成部材とする液晶表示素子を提供する。
Ring A is
(a) trans-1,4-cyclohexylene group (one CH 2 group present in this group or two or more non-adjacent CH 2 groups are replaced by -O- and / or -S- (May be)
(b) 1,4-phenylene group (one CH 2 group present in this group or two or more non-adjacent CH 2 groups may be replaced by -N-)
A group selected from the group consisting of: the group (a), the group (b) may be substituted with CH 3 or halogen,
Z 1 is each independently -CH 2 O-, -OCH 2- , -CF 2 O-, -OCF 2- , -CH 2 CH 2- , -CF 2 CF 2- , -CH = CH- , - (CH 2) 4 - , - CH = CH-CH 2 CH 2 -, - a CH 2 CH 2 -CH = CH- or a single bond,
Q 1 is -OCH2-, -OCF2-, -OCHF-, -CF2-, or a single bond,
X 1 to X 3 are each independently H, F or Cl. A liquid crystal composition for an active matrix type liquid crystal display element comprising one or two or more compounds selected from the group of compounds represented by the formula: and a liquid crystal display element comprising the liquid crystal composition as a constituent member provide.
本発明は液晶化合物のアルキレン鎖長の偶奇効果を見出すことによって、低い屈折率異方性(Δn=0.05〜0.13)を維持しつつ、低温で安定したネマチック相を持ち、液晶相温度範囲が広く、高い誘電率異方性を有し、粘性が低く、かつ信頼性に優れたアクティブマトリクス型液晶表示素子用液晶組成物が得られた。この組成物を用いることにより、動作温度範囲が広いアクティブマトリクス型液晶表示素子が提供され、反射または半透過モード等の液晶ディスプレイとして非常に実用的である。 The present invention finds an even-odd effect of the alkylene chain length of a liquid crystal compound, maintains a low refractive index anisotropy (Δn = 0.05 to 0.13), has a stable nematic phase at a low temperature, and has a wide liquid crystal phase temperature range. Thus, a liquid crystal composition for an active matrix liquid crystal display device having a high dielectric anisotropy, low viscosity and excellent reliability was obtained. By using this composition, an active matrix liquid crystal display element having a wide operating temperature range is provided, which is very practical as a liquid crystal display in a reflective or transflective mode.
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(1)で表される化合物群から1種または2種以上を含有するが、1種〜5種が好ましく、1種〜3種がより好ましい。
第一成分として一般式(1)で表される化合物群から選ばれる1種または2種以上の化合物の含有率は、5〜30質量%の範囲であることが好まく、10〜20質量%の範囲であることがより好ましい。また、mは0、1又は2であるが0又は1が好ましく、nは0、1又は2であるが0又は1が好ましい。
In the liquid crystal composition of the present invention, the first component contains one or two or more types from the compound group represented by the general formula (1), preferably 1 to 5 types, more preferably 1 to 3 types. preferable.
The content of one or more compounds selected from the compound group represented by the general formula (1) as the first component is preferably in the range of 5 to 30% by mass, and 10 to 20% by mass. More preferably, it is the range. M is 0, 1 or 2, but 0 or 1 is preferable, and n is 0, 1 or 2, but 0 or 1 is preferable.
Z1は、-CH2O-、-OCH2-、-CF2O-、-OCF2-、-CH2CH2-、-CF2CF2-、-CH=CH-、-(CH2)4-、-CH=CH-CH2CH2-、-CH2CH2-CH=CH- 又は単結合であるが、-CF2O-、-OCF2-、-CH2CH2-、-CF2CF2-、-CH=CH-又は単結合が好ましく、-CF2O-、-OCF2-、-CH2CH2-又は単結合がより好ましく、-CH2CH2-又は単結合が特に好ましい。Q1は-OCH2-、-OCF2-、-OCHF-、-CF2-、または単結合であるが、-OCF2-、-CF2-、または単結合が好ましく、単結合がより好ましい。X1〜X3はそれぞれ独立してH、F又はClであるが、-H、-Fが好ましく、X2はFが好ましい。
さらに詳述すると、一般式(1)の具体的な構造として以下の一般式(1a)
Z 1 is, -CH 2 O -, - OCH 2 -, - CF 2 O -, - OCF 2 -, - CH 2 CH 2 -, - CF 2 CF 2 -, - CH = CH -, - (CH 2 ) 4 -, - CH = CH -CH 2 CH 2 -, - CH 2 CH 2 -CH = CH- , or is a single bond, -CF 2 O -, - OCF 2 -, - CH 2 CH 2 -, -CF 2 CF 2- , -CH = CH- or a single bond is preferred, -CF 2 O-, -OCF 2- , -CH 2 CH 2 -or a single bond is more preferred, -CH 2 CH 2- or a single bond Bonding is particularly preferred. Q 1 is -OCH 2 -, - OCF 2 - , - OCHF -, - CF 2 -, or is a single bond, -OCF 2 -, - CF 2 -, or a single bond, more preferably a single bond is more preferable . X 1 to X 3 are each independently H, F or Cl, but —H and —F are preferred, and X 2 is preferably F.
More specifically, as a specific structure of the general formula (1), the following general formula (1a)
組成物の物性値を調整し、さらに低粘性化、低電圧化を達成させるために第二成分として、一般式(2) In order to adjust the physical properties of the composition and to achieve lower viscosity and lower voltage, as a second component, the general formula (2)
B1〜B3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個以上のCH2基は -O- 及び又は -S- に置き換えられてもよい)
(b) 1,4-フェニレン基(この基中に存在する1個のCH2基又は隣接していない2個以上のCH2基は -N- に置き換えられてもよい)
からなる群より選ばれる基であり、上記の基(a)、基(b)はCH3又はハロゲンで置換されていても良く、
qは0、1又は2であり、
L1、L2はそれぞれ独立的に単結合、-CH2CH2-、-(CH2)4-、-OCH2-、-CH2O-、-OCF2-、-CF2O-又は-C≡C-を表し、
B1及びL1が複数存在する場合はそれらは同一でも良く異なっていても良い。)で表される化合物群から選ばれる1種もしくは2種以上の化合物と、第三成分としてとして一般式(3)
B 1 to B 3 are each independently
(a) trans-1,4-cyclohexylene group (one CH 2 group present in this group or two or more non-adjacent CH 2 groups are replaced by -O- and / or -S- (May be)
(b) 1,4-phenylene group (one CH 2 group present in this group or two or more non-adjacent CH 2 groups may be replaced by -N-)
A group selected from the group consisting of: the group (a), the group (b) may be substituted with CH 3 or halogen,
q is 0, 1 or 2;
L 1 and L 2 are each independently a single bond, —CH 2 CH 2 —, — (CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —OCF 2 —, —CF 2 O—, or -C≡C-
When a plurality of B 1 and L 1 are present, they may be the same or different. ) Or one or more compounds selected from the group of compounds represented by the general formula (3) as the third component
B4、B5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個以上のCH2基は -O- 及び又は -S- に置き換えられてもよい)
(b) 1,4-フェニレン基(この基中に存在する1個のCH2基又は隣接していない2個以上のCH2基は -N- に置き換えられてもよい)
(c)ナフタレン-2,6-ジイル、デカヒドロナフタレン-2,6-ジイル及び1,2,3,4-テトラヒドロナフタレン-2,6-ジイル
からなる群より選ばれる基であり、上記の基(a)、基(b)、基(c)はCH3又はハロゲンで置換されていても良く、
rは1又は2であり、
L3、L4はそれぞれ独立的に単結合、-CH2CH2-、-(CH2)4-、-OCH2-、-CH2O-、-OCF2-、-CF2O-又は-C≡C-を表し、
B4及びL3が複数存在する場合はそれらは同一でも良く異なっていても良く、
Q2はQ1と同じ意味を表し、
X4〜X6はそれぞれ独立してH、F又はClである。)で表される化合物群から選ばれる化合物を1種又は2種以上を含有することが好ましい。
B 4 and B 5 are each independently
(a) trans-1,4-cyclohexylene group (one CH 2 group present in this group or two or more non-adjacent CH 2 groups are replaced by -O- and / or -S- (May be)
(b) 1,4-phenylene group (one CH 2 group present in this group or two or more non-adjacent CH 2 groups may be replaced by -N-)
(c) a group selected from the group consisting of naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl and 1,2,3,4-tetrahydronaphthalene-2,6-diyl, (a), group (b), group (c) may be substituted with CH 3 or halogen,
r is 1 or 2,
L 3 and L 4 are each independently a single bond, —CH 2 CH 2 —, — (CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —OCF 2 —, —CF 2 O—, or -C≡C-
When a plurality of B 4 and L 3 are present, they may be the same or different,
Q 2 has the same meaning as Q 1
X 4 to X 6 are each independently H, F or Cl. It is preferable to contain one or more compounds selected from the group of compounds represented by
一般式(2)で表される化合物は1種〜10種が好ましく、1種〜5種がより好ましく、1種〜3種がさらに好ましい。一般式(2)で表される化合物群から選ばれる1種または2種以上の化合物の含有率は、5〜40質量%の範囲であることが好まく、10〜35質量%の範囲であることがより好ましい。また、R1、R2は、炭素数1〜10のアルキル基又は炭素数2〜10のアルケニル基が好ましく、未置換の直鎖状炭素数1〜8のアルキル基又は炭素数2〜8のアルケニル基がより好ましく、アルケニル基では以下の式(a)〜(e)の構造がさらに好ましい。 As for the compound represented by General formula (2), 1 type-10 types are preferable, 1 type-5 types are more preferable, 1 type-3 types are more preferable. The content of one or more compounds selected from the compound group represented by the general formula (2) is preferably in the range of 5 to 40% by mass, and in the range of 10 to 35% by mass. It is more preferable. R 1 and R 2 are preferably an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, an unsubstituted linear alkyl group having 1 to 8 carbon atoms or an alkyl group having 2 to 8 carbon atoms. An alkenyl group is more preferable, and the structure of the following formulas (a) to (e) is more preferable as the alkenyl group.
B1、B2及びB3はトランス-1,4-シクロへキシレン基、1,4-フェニレン基、3-フルオロ-1,4-フェニレン基又は3,5-ジフルオロ-1,4-フェニレン基が好ましく、1,4-フェニレン基又はトランス-1,4-シクロへキシレン基がより好ましい。L1、L2はそれぞれ独立的に、単結合、-CH2CH2-、-(CH2)4-、-OCH2-、-CH2O-、-OCF2-、-CF2O-又は-C≡C-であるが、-CH2CH2-、-CH=CH-又は単結合が好ましく、-CH2CH2-又は単結合がより好ましい。qは0、1又は2であるが、0又は1であることが好ましい。
さらに詳述すると、一般式(2)の具体的な構造として次の化合物が特に好ましい。
B 1 , B 2 and B 3 are trans-1,4-cyclohexylene group, 1,4-phenylene group, 3-fluoro-1,4-phenylene group or 3,5-difluoro-1,4-phenylene group 1,4-phenylene group or trans-1,4-cyclohexylene group is more preferable. L 1 and L 2 are each independently a single bond, —CH 2 CH 2 —, — (CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —OCF 2 —, —CF 2 O— Or, —C≡C—, —CH 2 CH 2 —, —CH═CH— or a single bond is preferable, and —CH 2 CH 2 — or a single bond is more preferable. q is 0, 1 or 2, but is preferably 0 or 1.
More specifically, the following compounds are particularly preferred as the specific structure of the general formula (2).
第三成分として一般式(3)で表される化合物群を2種〜15種含有することが好ましく、2種〜10種がより好ましく、4種〜7種がさらに好ましい。 It is preferable to contain 2-15 types of compound groups represented by General formula (3) as a 3rd component, 2-10 types are more preferable, and 4-7 types are more preferable.
第三成分として一般式(3)または一般式(4)で表される化合物群から選ばれる1種または2種以上の化合物の含有率は、20〜70質量%の範囲であることがより好ましく、35〜65質量%の範囲であることがさらに好ましい。また、R3〜R5は、炭素数1〜10のアルキル基又は炭素数2〜10のアルケニル基が好ましく、未置換の直鎖状炭素数1〜8のアルキル基又は炭素数2〜8のアルケニル基がより好ましく、アルケニル基では式(a)〜(e)の構造がさらに好ましい。 The content of one or more compounds selected from the compound group represented by the general formula (3) or the general formula (4) as the third component is more preferably in the range of 20 to 70% by mass. More preferably, it is in the range of 35 to 65% by mass. R 3 to R 5 are preferably an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, an unsubstituted linear alkyl group having 1 to 8 carbon atoms or an alkyl group having 2 to 8 carbon atoms. Alkenyl groups are more preferred, and structures of formulas (a) to (e) are more preferred for alkenyl groups.
B4及びB5はトランス-1,4-シクロへキシレン基、1,4-フェニレン基、3-フルオロ-1,4-フェニレン基又は3,5-ジフルオロ-1,4-フェニレン基が好ましく、1,4-フェニレン基又はトランス-1,4-シクロへキシレン基がより好ましい。L3、L4は、単結合、-CH2CH2-、-(CH2)4-、-OCH2-、-CH2O-、-OCF2-、-CF2O-又は-C≡C-であるが、-CH2CH2-、-OCF2-、-CF2O-又は単結合が好ましく、-CH2CH2-、-CF2O-又は単結合がより好ましく、-CH2CH2-又は単結合が特に好ましい。rは0、1又は2であるが、1又は2が好ましい。 B 4 and B 5 are preferably trans-1,4-cyclohexylene group, 1,4-phenylene group, 3-fluoro-1,4-phenylene group or 3,5-difluoro-1,4-phenylene group, A 1,4-phenylene group or a trans-1,4-cyclohexylene group is more preferred. L 3 and L 4 are a single bond, —CH 2 CH 2 —, — (CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —OCF 2 —, —CF 2 O—, or —C≡. C—, —CH 2 CH 2 —, —OCF 2 —, —CF 2 O— or a single bond is preferred, —CH 2 CH 2 —, —CF 2 O— or a single bond is more preferred, —CH 2 2 CH 2 — or a single bond is particularly preferred. r is 0, 1 or 2, with 1 or 2 being preferred.
さらに詳述すると、一般式(3)は、具体的な構造として以下の一般式で表される化合物が好ましい。 More specifically, the general formula (3) is preferably a compound represented by the following general formula as a specific structure.
本発明において、ネマチック相-等方性液体相転移温度(TN-I)は80℃以上であることがより好ましく、90℃以上であることがさらに好ましい。固体相又はスメクチック相−ネマチック相転移温度(T→N)は-20℃以下であることが好ましく、-30℃以下であることがより好ましい。25℃における誘電率異方性(Δε)が4.5〜10.0であることが好ましく、5.0〜8.0であることがより好ましい。25℃における屈折率異方性(Δn)が0.05〜0.13であることが好ましい。 In the present invention, the nematic phase-isotropic liquid phase transition temperature (T NI ) is more preferably 80 ° C. or higher, and further preferably 90 ° C. or higher. The solid phase or smectic phase-nematic phase transition temperature (T → N ) is preferably −20 ° C. or lower, and more preferably −30 ° C. or lower. The dielectric anisotropy (Δε) at 25 ° C. is preferably 4.5 to 10.0, and more preferably 5.0 to 8.0. The refractive index anisotropy (Δn) at 25 ° C. is preferably 0.05 to 0.13.
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、反射モードまたは半透過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 a liquid crystal display element for driving an active matrix, and can be used for a liquid crystal display element for a reflection mode or a transflective mode.
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、以下の実施例およ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”.
TN-I :ネマチック相−等方性液体相転移温度(℃)を液晶相上限温度とする
T→N :固体相又はスメクチック相−ネマチック相転移温度(℃)を液晶相下限温度
とする。
Δε :誘電率異方性
Δn :屈折率異方性
HR :80℃での保持率(%)(セル厚6μmのTN-LCDに注入し、5V印加、フレームタ
イム200ms、パルス幅64μsで測定したときの測定電圧と初期印加電圧との
比を%で表した値。)
化合物記載に下記の略号を使用する。
末端のn(数字) CnH2n+1-
2 -CH2CH2-
On -OCnH2n+1
F -F
CFFF -CF3
OCFFF -OCF3
ndm- CnH2n+1-C=C-(CH2)m-1-
nOm- CnH2n+1-O-(CH2)m-1-
-E- -COO-
-1O- -CH2O-
T NI : Nematic phase-isotropic liquid phase transition temperature (° C) is the liquid crystal phase upper limit temperature
T → N : Solid phase or smectic phase-nematic phase transition temperature (° C) is the lower limit of liquid crystal phase temperature
And
Δε: dielectric anisotropy Δn: refractive index anisotropy
HR: Retention rate at 80 ° C (%) (Injected into TN-LCD with 6μm cell thickness, 5V applied, flame
Between the measured voltage and the initial applied voltage when measured at 200 ms and a pulse width of 64 μs.
Value expressed as a percentage. )
The following abbreviations are used in compound descriptions.
Terminal n (number) C n H 2n + 1-
2 -CH 2 CH 2-
On -OC n H 2n + 1
F -F
CFFF -CF 3
OCFFF -OCF 3
ndm- C n H 2n + 1 -C = C- (CH 2 ) m-1-
nOm- C n H 2n + 1 -O- (CH 2 ) m-1-
-E- -COO-
-1O- -CH 2 O-
(実施例1〜3) 液晶組成物の調整
以下に示すネマチック液晶組成物(No.1)〜(No.4)を調整しその物性値を測定し、その結果を表1に示す。
(Examples 1 to 3) Adjustment of liquid crystal composition Nematic liquid crystal compositions (No. 1) to (No. 4) shown below were prepared and their physical properties were measured, and the results are shown in Table 1.
実施例1〜4のネマチック液晶組成物(No.1) 〜(No.4)特性は、ネマチック相-等方性液体相転移温度(TN-I)、固体相又はスメクチック相−ネマチック相転移温度(T→N)、誘電率異方性(Δε)、屈折率異方性(Δn)全ての特性において所望の値を示した。また粘性も低く、パネルの応答速度も良好であり、さらに加熱150℃1時間後の保持率も初期の値を保っており信頼性が良好であった。 The nematic liquid crystal compositions (No. 1) to (No. 4) of Examples 1 to 4 have the following characteristics: nematic phase-isotropic liquid phase transition temperature (T NI ), solid phase or smectic phase-nematic phase transition temperature ( T → N ), dielectric anisotropy (Δε), and refractive index anisotropy (Δn) showed desired values. In addition, the viscosity was low, the response speed of the panel was good, and the retention after 1 hour of heating at 150 ° C. kept the initial value, and the reliability was good.
(比較例1〜4) 液晶組成物の調整
比較例として以下に示すネマチック液晶組成物(R1)〜(R4)を調整しその物性値を測定し、その結果を表2に示す。
(Comparative Examples 1 to 4) Adjustment of Liquid Crystal Composition As comparative examples, nematic liquid crystal compositions (R1) to (R4) shown below were prepared and their physical properties were measured. The results are shown in Table 2.
比較例1〜4のネマチック液晶組成物(R1) 〜(R4)特性は、ネマチック相-等方性液体相転移温度(TN-I)、固体相又はスメクチック相−ネマチック相転移温度(T→N)、誘電率異方性(Δε)、屈折率異方性(Δn)全ての特性において所望の値を示した。ただし粘性が実施例と比較して高く、パネルの応答速度も遅い結果となった。加熱150℃1時間後の保持率は実施例同様、初期の値を保っており信頼性は良好であった。 The nematic liquid crystal compositions (R1) to (R4) of Comparative Examples 1 to 4 have the following characteristics: nematic phase-isotropic liquid phase transition temperature (T NI ), solid phase or smectic phase-nematic phase transition temperature (T → N ) The dielectric anisotropy (Δε) and the refractive index anisotropy (Δn) all showed desired values. However, the viscosity was higher than that of the example and the panel response speed was slow. The retention rate after 1 hour of heating at 150 ° C. maintained the initial value as in the example, and the reliability was good.
(比較例5) 液晶組成物の調整
比較例として以下に示すネマチック液晶組成物(R5)を調整しその物性値を測定し、その結果を表3に示す。
(Comparative Example 5) Adjustment of Liquid Crystal Composition As a comparative example, the nematic liquid crystal composition (R5) shown below was prepared and measured for physical properties. The results are shown in Table 3.
比較例5のネマチック液晶組成物(R5)は第一成分、第三成分は含有しているものの第二成分を含有していない。このため粘性が実施例として高くパネルの応答速度が十分に高速ではなかった。またネマチック相-等方性液体相転移温度(TN-I)が75.2℃と低く、スメクチック相−ネマチック相転移温度(T→N)が高く、液晶相の温度範囲が狭いため実用的な液晶組成物としては使用することができないものであった。さらにさらに加熱150℃1時間後の保持率も初期の値から低下しており、十分な信頼性を有していなかった。 The nematic liquid crystal composition (R5) of Comparative Example 5 contains the first component and the third component, but does not contain the second component. For this reason, the viscosity was high as an example, and the response speed of the panel was not sufficiently high. In addition, the nematic phase-isotropic liquid phase transition temperature (T NI ) is as low as 75.2 ° C, the smectic phase-nematic phase transition temperature (T → N ) is high, and the temperature range of the liquid crystal phase is narrow. It could not be used as. Furthermore, the retention after 1 hour of heating at 150 ° C. also decreased from the initial value, and the reliability was not sufficient.
(比較例6) 液晶組成物の調整
比較例として以下に示すネマチック液晶組成物(R6)を調整しその物性値を測定し、その結果を表4に示す。
(Comparative Example 6) Preparation of liquid crystal composition As a comparative example, the nematic liquid crystal composition (R6) shown below was prepared and measured for physical properties. The results are shown in Table 4.
比較例6のネマチック液晶組成物(R6)の特性は、ネマチック相-等方性液体相転移温度(TN-I)が81.4℃と低く、液晶相の温度範囲がやや狭いため実用的な液晶組成物としては十分なものではなかった。また第一成分、第二成分、第三成分の全てを含有しているものの、その他の成分としてエステル化合物が含有されており、加熱150℃1時間後の保持率が初期の値から低下し、十分な信頼性を有していなかった。 The characteristics of the nematic liquid crystal composition (R6) of Comparative Example 6 are practical liquid crystal compositions because the nematic phase-isotropic liquid phase transition temperature (T NI ) is as low as 81.4 ° C and the temperature range of the liquid crystal phase is somewhat narrow. As it was not enough. Although it contains all of the first component, the second component, and the third component, an ester compound is contained as the other component, and the retention after heating at 150 ° C. for 1 hour decreases from the initial value, It was not reliable enough.
(比較例7) 液晶組成物の調整
比較例として以下に示すネマチック液晶組成物(R7)を調整しその物性値を測定し、その結果を表5に示す。
(Comparative Example 7) Preparation of liquid crystal composition As a comparative example, the nematic liquid crystal composition (R7) shown below was prepared and measured for physical properties. The results are shown in Table 5.
比較例7のネマチック液晶組成物(R7)の特性は、ネマチック相-等方性液体相転移温度(TN-I)が80.0℃と低く、液晶相の温度範囲がやや狭いため実用的な液晶組成物としては十分なものではなかった。
The characteristics of the nematic liquid crystal composition (R7) of Comparative Example 7 are practical liquid crystal compositions because the nematic phase-isotropic liquid phase transition temperature (T NI ) is as low as 80.0 ° C and the temperature range of the liquid crystal phase is somewhat narrow. As it was not enough.
Claims (6)
環Aは
(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個以上のCH2基は -O- 及び又は -S- に置き換えられてもよい)
(b) 1,4-フェニレン基(この基中に存在する1個のCH2基又は隣接していない2個以上のCH2基は -N- に置き換えられてもよい)
からなる群より選ばれる基であり、上記の基(a)、基(b)はCH3又はハロゲンで置換されていても良く、
Z1はそれぞれ独立的には、-CH2O-、-OCH2-、-CF2O-、-OCF2-、-CH2CH2-、-CF2CF2-、-CH=CH-、-(CH2)4-、-CH=CH-CH2CH2-、-CH2CH2-CH=CH- 又は単結合であり、
Q1は-OCH2-、-OCF2-、-OCHF-、-CF2-、または単結合であり、
X1〜X3はそれぞれ独立してH、F又はClである。)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ことを特徴とするアクティブマトリクス型液晶表示素子用液晶組成物。 General formula (1) as the first component,
Ring A is
(a) trans-1,4-cyclohexylene group (one CH 2 group present in this group or two or more non-adjacent CH 2 groups are replaced by -O- and / or -S- (May be)
(b) 1,4-phenylene group (one CH 2 group present in this group or two or more non-adjacent CH 2 groups may be replaced by -N-)
A group selected from the group consisting of the above group (a), the group (b) may be substituted with CH 3 or halogen,
Z 1 is each independently -CH 2 O-, -OCH 2- , -CF 2 O-, -OCF 2- , -CH 2 CH 2- , -CF 2 CF 2- , -CH = CH- , - (CH 2) 4 - , - CH = CH-CH 2 CH 2 -, - a CH 2 CH 2 -CH = CH- or a single bond,
Q 1 is —OCH 2 —, —OCF 2 —, —OCHF—, —CF 2 —, or a single bond,
X 1 to X 3 are each independently H, F or Cl. A liquid crystal composition for an active matrix liquid crystal display device, comprising one or more compounds selected from the group of compounds represented by
B1〜B3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個以上のCH2基は -O- 及び又は -S- に置き換えられてもよい)
(b) 1,4-フェニレン基(この基中に存在する1個のCH2基又は隣接していない2個以上のCH2基は -N- に置き換えられてもよい)
からなる群より選ばれる基であり、上記の基(a)、基(b)はCH3又はハロゲンで置換されていても良く、
qは0、1又は2であり、
L1、L2はそれぞれ独立的に単結合、-CH2CH2-、-(CH2)4-、-OCH2-、-CH2O-、-OCF2-、-CF2O-又は-C≡C-を表し、
B1及びL1が複数存在する場合はそれらは同一でも良く異なっていても良い。)で表される化合物群から選ばれる1種もしくは2種以上の化合物と、第三成分としてとして一般式(3)
B4、B5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個以上のCH2基は -O- 及び又は -S- に置き換えられてもよい)
(b) 1,4-フェニレン基(この基中に存在する1個のCH2基又は隣接していない2個以上のCH2基は -N- に置き換えられてもよい)
(c)ナフタレン-2,6-ジイル、デカヒドロナフタレン-2,6-ジイル及び1,2,3,4-テトラヒドロナフタレン-2,6-ジイル
からなる群より選ばれる基であり、上記の基(a)、基(b)、基(c)はCH3又はハロゲンで置換されていても良く、
rは1又は2であり、
L3、L4はそれぞれ独立的に単結合、-CH2CH2-、-(CH2)4-、-OCH2-、-CH2O-、-OCF2-、-CF2O-又は-C≡C-を表し、
B4及びL3が複数存在する場合はそれらは同一でも良く異なっていても良く、
Q2はQ1と同じ意味を表し、
X4〜X6はそれぞれ独立してH、F又はClである。) で表される化合物群から選ばれる1種もしくは2種以上の化合物からなることを特徴とする請求項1記載のネマチック液晶組成物。 General formula (2) as the second component,
B 1 to B 3 are each independently
(a) trans-1,4-cyclohexylene group (one CH 2 group present in this group or two or more non-adjacent CH 2 groups are replaced by -O- and / or -S- (May be)
(b) 1,4-phenylene group (one CH 2 group present in this group or two or more non-adjacent CH 2 groups may be replaced by -N-)
A group selected from the group consisting of: the group (a), the group (b) may be substituted with CH 3 or halogen,
q is 0, 1 or 2;
L 1 and L 2 are each independently a single bond, —CH 2 CH 2 —, — (CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —OCF 2 —, —CF 2 O—, or -C≡C-
When a plurality of B 1 and L 1 are present, they may be the same or different. ) Or one or more compounds selected from the group of compounds represented by the general formula (3) as the third component
B 4 and B 5 are each independently
(a) trans-1,4-cyclohexylene group (one CH 2 group present in this group or two or more non-adjacent CH 2 groups are replaced by -O- and / or -S- (May be)
(b) 1,4-phenylene group (one CH 2 group present in this group or two or more non-adjacent CH 2 groups may be replaced by -N-)
(c) a group selected from the group consisting of naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl and 1,2,3,4-tetrahydronaphthalene-2,6-diyl, (a), group (b), group (c) may be substituted with CH 3 or halogen,
r is 1 or 2,
L 3 and L 4 are each independently a single bond, —CH 2 CH 2 —, — (CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —OCF 2 —, —CF 2 O—, or -C≡C-
When a plurality of B 4 and L 3 are present, they may be the same or different,
Q 2 has the same meaning as Q 1
X 4 to X 6 are each independently H, F or Cl. 2. The nematic liquid crystal composition according to claim 1, wherein the nematic liquid crystal composition is composed of one or more compounds selected from the group of compounds represented by:
An active matrix liquid crystal display device using the nematic liquid crystal composition according to claim 1.
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WO2016133035A1 (en) * | 2015-02-17 | 2016-08-25 | Jnc株式会社 | Compound having saturated six-membered ring and alkoxy group or alkoxyalkyl group, liquid crystal composition and liquid crystal display element |
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JP2018021089A (en) * | 2016-08-01 | 2018-02-08 | Jnc株式会社 | Liquid crystal composition and liquid crystal display element |
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