JPH0436384A - Additive for liquid crystal and liquid crystal composition comprising it - Google Patents
Additive for liquid crystal and liquid crystal composition comprising itInfo
- Publication number
- JPH0436384A JPH0436384A JP2140082A JP14008290A JPH0436384A JP H0436384 A JPH0436384 A JP H0436384A JP 2140082 A JP2140082 A JP 2140082A JP 14008290 A JP14008290 A JP 14008290A JP H0436384 A JPH0436384 A JP H0436384A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- additive
- formula
- display
- crystal composition
- 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.)
- Pending
Links
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 16
- 239000000654 additive Substances 0.000 title claims abstract description 6
- 230000000996 additive effect Effects 0.000 title abstract description 4
- 150000001767 cationic compounds Chemical class 0.000 claims description 3
- 229910001411 inorganic cation Inorganic materials 0.000 claims description 3
- 150000002892 organic cations Chemical class 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 230000002159 abnormal effect Effects 0.000 abstract description 2
- 150000001768 cations Chemical class 0.000 abstract description 2
- 230000002950 deficient Effects 0.000 abstract 1
- 239000011734 sodium Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 5
- 230000007547 defect Effects 0.000 description 5
- -1 quaternary ammonium ions Chemical class 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 3
- 230000005611 electricity Effects 0.000 description 3
- 230000003068 static effect Effects 0.000 description 3
- WOLVEMPZUIFSII-IHHOKICGSA-N (2e,4e)-n-[(2s,5s)-5-(hydroxymethyl)-1-methyl-3-oxo-2-propan-2-yl-2,4,5,6-tetrahydro-1,4-benzodiazocin-8-yl]-5-[4-(trifluoromethyl)phenyl]penta-2,4-dienamide Chemical compound CN([C@H](C(N[C@H](CO)CC1=C2)=O)C(C)C)C1=CC=C2NC(=O)\C=C\C=C\C1=CC=C(C(F)(F)F)C=C1 WOLVEMPZUIFSII-IHHOKICGSA-N 0.000 description 2
- 101100046776 Arabidopsis thaliana TPPB gene Proteins 0.000 description 2
- PQBAWAQIRZIWIV-UHFFFAOYSA-N N-methylpyridinium Chemical compound C[N+]1=CC=CC=C1 PQBAWAQIRZIWIV-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 210000002858 crystal cell Anatomy 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- NDZFNTHGIIQMQI-UHFFFAOYSA-N 1-benzylpyridin-1-ium Chemical compound C=1C=CC=C[N+]=1CC1=CC=CC=C1 NDZFNTHGIIQMQI-UHFFFAOYSA-N 0.000 description 1
- VDPIZIZDKPFXLI-UHFFFAOYSA-N 1-iodo-3,5-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(I)=CC(C(F)(F)F)=C1 VDPIZIZDKPFXLI-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005685 electric field effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 229910001410 inorganic ion Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、液晶表示において、静電気による表示欠陥を
少なくするための耐久性良好な抵抗値低下剤およびそれ
を含有する液晶組成物に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a resistance value lowering agent with good durability and a liquid crystal composition containing the same for reducing display defects caused by static electricity in liquid crystal displays. be.
〔従来の技術及び発明が解決しようとする！！題）現在
、実用化されている液晶表示法は数多いが、これらのほ
とんどは電界効果を利用している。を界効果を利用する
表示は電場による作動なので電荷の流れは極力抑制しな
ければならず、省エネルギーである点を特徴としている
。[Conventional techniques and inventions try to solve the problem! ! There are many liquid crystal display methods currently in practical use, but most of them utilize electric field effects. Displays that utilize field effects are operated by electric fields, so the flow of charge must be suppressed as much as possible, and they are characterized by energy savings.
この要望に対応して液晶化合物が高純度化し、比抵抗値
が近年、非常に高くなってきている。In response to this demand, liquid crystal compounds have become highly purified, and their specific resistance values have become extremely high in recent years.
一方、液晶の比抵抗値の向上に伴い、新たな問題として
静電気による表示欠陥が起こることが判明した。液晶表
示の高品位化が進むに従って、この点が大きな問題点に
なった。On the other hand, it has been discovered that as the resistivity of liquid crystals improves, display defects due to static electricity occur as a new problem. As the quality of liquid crystal displays has become higher, this has become a major problem.
上記問題点を解決する１つの方法として、４級アンモニ
ウムイオン等のイオン性化合物、テトラシアノキノジメ
タン等の強電子受容性化合物などを液晶に添加して使用
することが日本特許（特開昭５９−４６７６号）に記載
されている。One method to solve the above problems is to add ionic compounds such as quaternary ammonium ions, strong electron-accepting compounds such as tetracyanoquinodimethane, etc. 59-4676).
しかしながら、これらの添加物は長時間使用すれば分解
するため機能しなくなることが確認された。However, it has been confirmed that these additives decompose and cease to function if used for a long time.
また、比抵抗値は１０９〜５Ｘ１０”Ω・１に調整する
必要があると記載されているが、最近の液晶セル技術で
は、５Ｘ１０’°Ω・ｌを超え１０Ｉ：Ω・１以下の領
域では表示欠陥が起こらなくなっているので、省エネル
ギーの観点からは５Ｘ１０’°Ω・１〜１０１！Ω・１
である方が望まれている。Also, it is stated that the specific resistance value needs to be adjusted to 109~5X10''Ω・1, but with recent liquid crystal cell technology, in the region exceeding 5X10'°Ω・l and below 10I:Ω・1, Since display defects no longer occur, from the point of view of energy saving, 5X10'°Ω・1~101!Ω・1
It is desired that
本発明者らは、耐久性が良好であり表示品位を損なうこ
とのない抵抗値調整剤について鋭意検討した結果、次式
（Ｉ）
〔式中、Ｘ”は有機および無機のカチオンを示し、ｎは
１または２の整数を示す。〕で表されるホウ酸化合物が
極めて有効であることを見出し、発明を完成するに至っ
た。The present inventors have conducted intensive studies on resistance value adjusting agents that have good durability and do not impair display quality, and have found that the following formula (I) [wherein X'' represents an organic or inorganic cation, n represents an integer of 1 or 2.] It was discovered that a boric acid compound represented by the following is extremely effective, and the invention was completed.
以下、本発明の詳細な説明する。The present invention will be explained in detail below.
Ｘｏの具体例として有機イオンにはテトラメチルアンモ
ニウム、テトラブチルアンモニウム、ベンジルトリメチ
ルアンモニウムなどのアンモニウムイオン、Ｎ−メチル
ピリジニウム、Ｎ−ベンジルピリジニウムなどのピリジ
ニウムイオン、テトラフェニルホスホニウム、テトラブ
チルホスホニウムなどのホスホニウムイオンが挙げられ
、無機イオンにはＬｉ”＋ Ｎａ’、 Ｋ’＋ Ｃｓ”
等が挙げられる。Specific examples of Xo include ammonium ions such as tetramethylammonium, tetrabutylammonium, benzyltrimethylammonium, pyridinium ions such as N-methylpyridinium and N-benzylpyridinium, and phosphonium ions such as tetraphenylphosphonium and tetrabutylphosphonium. Inorganic ions include Li"+ Na', K'+ Cs"
etc.
ｘＺ−の具体例としてはＭｇ”、 Ｃａ”、 Ｎｉ”、
Ｃｕ”Ｆｅ” Ｚｎ”などが挙げられる。Specific examples of xZ- include Mg”, Ca”, Ni”,
Examples include "Cu"Fe""Zn".
対カチオンがＮａ”であるテトラキス〔３，５−ビス（
トリフルオロメチル）フェニル］ホウ酸ナトリウム（以
後ＴＰＰＢ−と略記する。）については、公知の文献（
Ｈ，Ｎ１５ｈｉｄａ、 Ｎ、Ｔａｋａｄａ、 Ｍ、Ｙｏ
ｓｈｉｍｕｒａ。Tetrakis[3,5-bis(
Sodium trifluoromethyl)phenyl]borate (hereinafter abbreviated as TPPB-) is described in the known literature (
H, N15hida, N, Takada, M, Yo
Shimura.
Ｔ、５ｏｎｏｄａ、 Ｈ，Ｋｏｂａｙａｓｈｉ、 Ｂｕ
ｌｌ、 Ｃｈｅｗ、 Ｓｏｃ、 Ｊｐｎ。T, 5onoda, H, Kobayashi, Bu
ll, Chew, Soc, Jpn.
５７巻、 ２６００ページ、 １９８４年）に合成法を
示してあ即ち、５−ヨード−１，３−ビス（トリフルオ
ロメチル）ベンゼンをエーテル溶媒中、マグネシウムと
反応させグリニヤール試薬とした後に、三フフ化ホウ素
エーテル付加体と反応させ、炭酸ナトリウム水溶液中に
加えることによって得ることが出来る。57, p. 2600, 1984) shows a synthesis method in which 5-iodo-1,3-bis(trifluoromethyl)benzene is reacted with magnesium in an ether solvent to form a Grignard reagent, and then trifufu It can be obtained by reacting with a boron ether adduct and adding it to an aqueous sodium carbonate solution.
また、本化合物は種々の苛酷な条件下でも安定であるこ
とが報告されている。他の対カチオン化合物については
、イオン交換樹脂カラムによって化学的にＮａ”と交換
すれば容易に得られる。It has also been reported that this compound is stable under various harsh conditions. Other countercation compounds can be easily obtained by chemically exchanging Na'' using an ion exchange resin column.
本添加物の濃度は用いる液晶や表示セルによって異なる
が、０．０１〜１ｏｐｐｍ好ましくは０．１〜５ｐｐｍ
の範囲で用いると表示品位に影響がなく、静電気による
欠陥もないことが判明した。The concentration of this additive varies depending on the liquid crystal and display cell used, but is 0.01 to 1 oppm, preferably 0.1 to 5 ppm.
It was found that there was no effect on display quality and no defects due to static electricity when used within the range of .
本発明の式（Ｉ）で表される化合物を、比抵抗値が５Ｘ
ｌＯ”〜１０１２Ω・１になるように添加した液晶組成
物を用いた液晶セルの表示では、表示欠陥も起こらず、
電圧印加、電圧切断の操作を長期に亘って行っても比抵
抗値は変わらず異常表示もみられず、実用上価値ある液
晶添加物である。The compound represented by formula (I) of the present invention has a specific resistance value of 5X
In the display of a liquid crystal cell using a liquid crystal composition added so as to have a value of 1O"~1012Ω・1, no display defects occur,
Even if voltage application and voltage cutting operations are performed over a long period of time, the resistivity value remains unchanged and no abnormal display is observed, making it a practically valuable liquid crystal additive.
実施例 以下に実施例によって詳細に説明する。Example Examples will be described in detail below.
実施例１
メルク社製ＺＬＩ−１５６５中に種々の濃度のＴＰＰＢ
−Ｎａ”を添加し、液体用電極セル（川口電機型ＬＰ−
０５）に入れ、比抵抗値測定を川口電機製ユニバーサル
エレクトロメーターＭＭＡ ｌｌ−１７によって行った
。なお、測定はすべて２０°Ｃの恒温室内で行った。Example 1 Various concentrations of TPPB in Merck ZLI-1565
-Na" is added to the liquid electrode cell (Kawaguchi Electric type LP-
05), and the specific resistance value was measured using a universal electrometer MMA ll-17 manufactured by Kawaguchi Electric. Note that all measurements were performed in a constant temperature room at 20°C.
その結果を表−１に示す。The results are shown in Table-1.
表−１で示される通り、ＴＰＰＢ−Ｎａ’の添加量は０
．１〜５１１ｐ１ｍの範囲で使用すべきであることがわ
かる。As shown in Table 1, the amount of TPPB-Na' added was 0.
．． It can be seen that it should be used within the range of 1 to 511 p1m.
さらに、ｏ、ｓｐｐｍのＴＦＰＢ−Ｎａ”を含むＺＬ１
４５６５をポリイミド配向膜を施したＴＮセルに注入し
、５ｖの電圧を印加を２秒、電圧を切って２秒という操
作を１０６回繰り返したが全く比抵抗値は変化せず、ま
た、異常表示も見られず良好であった。Furthermore, ZL1 containing o, sppm of TFPB-Na”
4565 was injected into a TN cell with a polyimide alignment film, and the operation of applying a voltage of 5V for 2 seconds and turning off the voltage for 2 seconds was repeated 106 times, but the resistivity value did not change at all, and no abnormality was displayed. It was in good condition with no visible signs.
表−１ 示も見られず良好な結果を得た。Table-1 Good results were obtained with no visible signs.
さらに、他のカチオン、例えばＮ−メチルピリジニウム
やＣａ”を有するＴＦＰＢ−化合物も全く同様に良好な
結果が得られた。Furthermore, just as good results were obtained with TFPB-compounds having other cations, such as N-methylpyridinium and Ca''.
２、ｌＸ１０”
３．２Ｘ１０”
８．７Ｘ１０”
４．６Ｘ１０”
２．２Ｘ１０”
５．７Ｘ１０”
１、ｌＸ１０’・
８．０Ｘ１０”
５．２Ｘ１０”
特許出願人 三井東圧化学株式会社
実施例２
実施例１においてＴＰＰＢ−Ｎａ”の代わりにＴＰＰＢ
−ｕ（ｃ４ｕ＊）ａ） ４をｏ、５ｐｐ−添加したとこ
ろ、比挺抗値は２．８Ｘ１０”Ω・１を示した。2, lX10"3.2X10"8.7X10"4.6X10"2.2X10"5.7X10" 1, lX10'・8.0X10"5.2X10" Patent applicant Mitsui Toatsu Chemical Co., Ltd. Example 2 Implementation In Example 1, instead of TPPB-Na”, TPPB
-u(c4u*)a) When 5pp- of 4 was added, the specific resistance value was 2.8×10”Ω·1.
Claims (1)
、ｎは１または２の整数を示す。〕で表される液晶添加
物。 ２、式（ I ） ▲数式、化学式、表等があります▼（ I ） 〔式中、Ｘ＾ｍ＾＋は有機および無機のカチオンを示し
、ｎは１または２の整数を示す。〕で表される化合物を
添加して、比抵抗値が５×１０＾１＾０Ω・ｃｍを超え
、１０＾１＾２Ω・ｃｍ以下であることを特徴とする液
晶組成物。[Claims] 1. Formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, X^m^+ represents an organic or inorganic cation, and n is an integer of 1 or 2. shows. ] Liquid crystal additives. 2. Formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, X^m^+ represents an organic and inorganic cation, and n represents an integer of 1 or 2. ] A liquid crystal composition having a specific resistance value of more than 5×10^1^0 Ω·cm and not more than 10^1^2 Ω·cm.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2140082A JPH0436384A (en) | 1990-05-31 | 1990-05-31 | Additive for liquid crystal and liquid crystal composition comprising it |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2140082A JPH0436384A (en) | 1990-05-31 | 1990-05-31 | Additive for liquid crystal and liquid crystal composition comprising it |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0436384A true JPH0436384A (en) | 1992-02-06 |
Family
ID=15260543
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2140082A Pending JPH0436384A (en) | 1990-05-31 | 1990-05-31 | Additive for liquid crystal and liquid crystal composition comprising it |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0436384A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE112006001453T5 (en) | 2005-06-09 | 2008-11-06 | Adeka Corp. | New compound and liquid crystal composition |
-
1990
- 1990-05-31 JP JP2140082A patent/JPH0436384A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE112006001453T5 (en) | 2005-06-09 | 2008-11-06 | Adeka Corp. | New compound and liquid crystal composition |
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