JP2001316670A - Liquid crystal composition - Google Patents
Liquid crystal compositionInfo
- Publication number
- JP2001316670A JP2001316670A JP2000133403A JP2000133403A JP2001316670A JP 2001316670 A JP2001316670 A JP 2001316670A JP 2000133403 A JP2000133403 A JP 2000133403A JP 2000133403 A JP2000133403 A JP 2000133403A JP 2001316670 A JP2001316670 A JP 2001316670A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- crystal composition
- compound
- formula
- isoquinoline
- 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 75
- 239000000203 mixture Substances 0.000 title claims abstract description 49
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000004988 Nematic liquid crystal Substances 0.000 claims abstract description 4
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims abstract description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 8
- 230000000694 effects Effects 0.000 abstract description 7
- 230000003068 static effect Effects 0.000 abstract description 2
- 238000012360 testing method Methods 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 6
- 238000000691 measurement method Methods 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- 230000005669 field effect Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- 210000004460 N cell Anatomy 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000007257 malfunction Effects 0.000 description 1
- 238000010295 mobile communication Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
Abstract
Description
【0001】[0001]
【産業上の利用分野】本発明は、式(1)で示されるイソ
キノリン若しくはイソキノリン構造を有する化合物、式
(2)で示されるキナルジン若しくはキナルジン構造を有
する化合物、式(3)で示されるキノキサリン若しくはキ
ノキサリン構造を有する化合物のいずれか一つ若しくは
任意の組み合わせで添加することを特徴とする、比抵抗
が少なくとも1.0×1011Ωcmを有する液晶組成物及びこ
れを用いた液晶表示素子、特に電界効果型液晶表示素子
に関する。The present invention relates to an isoquinoline represented by the formula (1) or a compound having an isoquinoline structure,
A compound having a quinaldine or a compound having a quinaldine structure represented by (2), characterized by being added with any one or any combination of quinoxaline or a compound having a quinoxaline structure represented by the formula (3), the specific resistance is at least The present invention relates to a liquid crystal composition having 1.0 × 10 11 Ωcm and a liquid crystal display device using the same, particularly to a field effect liquid crystal display device.
【0002】[0002]
【従来の技術】液晶表示素子、特に電界効果型液晶表示
素子は、時計、電卓、移動通信携帯端末、OA機器、家電
製品など様々な用途に使用されている。これの電界効果
型液晶表示素子には、帯電が生じることによる誤作動の
問題があった。これに対して、特開昭59-4676には、四
級アンモニウム塩等のイオン性物質を添加し、比抵抗を
1010Ωcmまで下げ、電流を流すことにより帯電を防止す
る方法が提案されている。しかし、このようなイオン性
物質の添加は液晶の表示特性・信頼性に悪影響を与え、
表示不良を起こしてしまう欠点があった。このため、液
晶の表示特性に影響を及ぼさず、長期信頼性も高い帯電
防止効果のある液晶組成物及び液晶表示素子が求められ
ていた。2. Description of the Related Art Liquid crystal display devices, particularly field-effect type liquid crystal display devices, are used in various applications such as watches, calculators, mobile communication portable terminals, OA equipment, and home appliances. Such a field effect type liquid crystal display element has a problem of malfunction due to charging. On the other hand, JP-A-59-4676 discloses a method in which an ionic substance such as a quaternary ammonium salt is added to reduce the specific resistance.
A method has been proposed in which charging is prevented by lowering the current to 10 10 Ωcm and passing a current. However, the addition of such ionic substances adversely affects the display characteristics and reliability of the liquid crystal,
There is a drawback that display failure occurs. Therefore, there has been a demand for a liquid crystal composition and a liquid crystal display element having an antistatic effect that does not affect the display characteristics of the liquid crystal and has high long-term reliability.
【0003】[0003]
【発明が解決しようとする課題】本発明の解決しようと
する課題は、液晶の表示特性に影響を及ぼさず、長期信
頼性も高い帯電防止効果のある液晶組成物及び液晶表示
素子を提供することにある。SUMMARY OF THE INVENTION It is an object of the present invention to provide a liquid crystal composition and a liquid crystal display element having an antistatic effect which does not affect the display characteristics of the liquid crystal and has a high long-term reliability. It is in.
【0004】[0004]
【課題を解決するための手段】本発明は、上記課題を解
決するために、以下の液晶組成物及び液晶組成物を使用
した液晶表示素子を見出した。In order to solve the above-mentioned problems, the present invention has found the following liquid crystal composition and a liquid crystal display device using the liquid crystal composition.
【0005】発明1 少なくとも1.0×1011Ωcmの比抵抗
を有する液晶組成物であって、式(1)で示されるイソキ
ノリン若しくはイソキノリン構造を有する化合物、式
(2)で示されるキナルジン若しくはキナルジン構造を有
する化合物、式(3)で示されるキノキサリン若しくはキ
ノキサリン構造を有する化合物のいずれか一つ若しくは
その任意の組み合わせである成分Aを含有することを特
徴とするネマチック液晶組成物。Invention 1 A liquid crystal composition having a specific resistance of at least 1.0 × 10 11 Ωcm, comprising an isoquinoline represented by the formula (1) or a compound having an isoquinoline structure,
(2) a quinaldine or a compound having a quinaldine structure represented by the formula (3), a quinoxaline represented by the formula (3) or a compound having a quinoxaline structure, characterized by containing a component A which is any one or any combination thereof Nematic liquid crystal composition.
【0006】[0006]
【化2】 Embedded image
【0007】発明2 成分Aの含有量が0.01〜10.0質量%
であることを特徴とする発明1記載の液晶組成物。 発明3 帯電時間が30秒以下であることを特徴とする発
明1または2記載の液晶組成物。 発明4 電圧保持率が70%から85%であることを特徴とす
る発明1または2記載の液晶組成物。 発明5 発明1から3記載の液晶組成物を使用した液晶表
示素子。 発明6 液晶表示素子の帯電を改善する方法であって、
発明1から3記載の液晶組成物を液晶表示素子に使用する
ことを特徴とする方法。Invention 2 The content of the component A is 0.01 to 10.0% by mass.
The liquid crystal composition according to invention 1, wherein Invention 3 The liquid crystal composition according to Invention 1 or 2, wherein the charging time is 30 seconds or less. Invention 4 The liquid crystal composition according to Invention 1 or 2, wherein the voltage holding ratio is 70% to 85%. Invention 5 A liquid crystal display device using the liquid crystal composition according to any one of Inventions 1 to 3. Invention 6 is a method for improving charging of a liquid crystal display element,
A method comprising using the liquid crystal composition according to any one of Inventions 1 to 3 for a liquid crystal display device.
【0008】[0008]
【発明の実施の形態】以下に発明の一例について説明す
る。発明1 において液晶組成物の比抵抗は1.0×1011Ωc
m〜1.0×1013Ωcmであることが好ましく、特に好ましく
は1.0×1011Ωcm〜5.0×1012Ωcmであり、更に好ましく
は、1.0×1011Ωcm〜1.0×1012Ωcmである。またイソキ
ノリンを含有することが好ましい。DESCRIPTION OF THE PREFERRED EMBODIMENTS An example of the present invention will be described below. In the invention 1, the specific resistance of the liquid crystal composition is 1.0 × 10 11 Ωc
It is preferably m~1.0 × 10 13 Ωcm, particularly preferably 1.0 × 10 11 Ωcm~5.0 × 10 12 Ωcm, more preferably from 1.0 × 10 11 Ωcm~1.0 × 10 12 Ωcm. Further, it preferably contains isoquinoline.
【0009】発明2 において成分Aの化合物の含有量は
0.01〜5.0質量%であることが好ましく、特に0.01〜1.0
質量%であることが好ましい。In the invention 2, the content of the compound of the component A is
It is preferably 0.01 to 5.0% by mass, particularly 0.01 to 1.0% by mass.
It is preferable that the content is mass%.
【0010】発明3 において帯電時間が30秒以下である
が、20秒以下であることが特に好ましい。In the invention 3, the charging time is 30 seconds or less, and particularly preferably 20 seconds or less.
【0011】発明4 において液晶表示素子は電界効果型
液晶表示素子が適しているが、詳細には60°から360°
のねじり角を有するねじれ型液晶表示素子、例えばTN
(ツイステッドネマチック)表示素子若しくは超ねじれ型
液晶表示素子、例えばSTN(スーパーツイステッドネマチ
ック)液晶表示素子が適している。またねじれを有して
いない液晶表示素子や、IPS(インプレーンスイッチン
グ)液晶表示素子にも適用することができる。In the invention 4, a field effect type liquid crystal display element is suitable for the liquid crystal display element.
Liquid crystal display device having a twist angle of, for example, TN
A (twisted nematic) display element or a super twist type liquid crystal display element, for example, an STN (super twisted nematic) liquid crystal display element is suitable. Further, the present invention can be applied to a liquid crystal display element having no twist and an IPS (in-plane switching) liquid crystal display element.
【0012】ネマチック液晶組成物は、5種以上、好ま
しくは10種以上の液晶化合物を含有し、0.03〜0.30の光
学異方性を有することが好ましく、更に好ましくは0.05
〜0.20である。液晶組成物の誘電異方性は少なくとも
3、好ましくは5以上であることが好ましい。液晶組成物
のネマチック−アイソトロピック相転移温度は、少なく
とも70℃以上、特に好ましくは少なくとも80℃以上であ
る。The nematic liquid crystal composition contains 5 or more, preferably 10 or more liquid crystal compounds and preferably has an optical anisotropy of 0.03 to 0.30, more preferably 0.05 to 0.30.
~ 0.20. The dielectric anisotropy of the liquid crystal composition is at least
3, preferably 5 or more. The liquid crystal composition has a nematic-isotropic phase transition temperature of at least 70 ° C, particularly preferably at least 80 ° C.
【0013】[0013]
【実施例】以下、実施例を挙げて本発明を更に詳述する
が、本発明はこれらの実施例に限定されるものではな
い。また、以下の実施例の組成物における「%」は『質
量%』を意味する。EXAMPLES The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples. Further, “%” in the compositions of the following examples means “% by mass”.
【0014】化合物の記載に下記の略号を使用する。 末端のn(数字) : CnH2n+1- ndm- : CnH2n+1-C=C-(CH2)m-1- -T- : -C≡C- -VO- : -COO- F : -F On : -OCnH2n+1 The following abbreviations are used in describing the compounds. Terminal n (number): C n H 2n + 1 -ndm-: C n H 2n + 1 -C = C- (CH 2 ) m-1 --T-: -C≡C- -VO-:- COO- F: -F On: -OC n H 2n + 1
【0015】[0015]
【化3】 Embedded image
【0016】例えば、以下に示すように略号を用いる。For example, abbreviations are used as shown below.
【0017】[0017]
【化4】 Embedded image
【0018】(実施例1、比較例1)液晶組成物Rを常法
に従い作成した。得られた液晶組成物Rにイソキノリン
を1.0質量%添加して本発明に係わる液晶組成物Mを作成
した。比較例としてイソキノリン無添加の液晶組成物R
及び本発明に係わる液晶組成物Mを90°ねじれの TNセル
に注入し、帯電時間(sec)、電気光学特性、電圧保持率
(%)、相転移温度(℃)を測定した。Example 1, Comparative Example 1 A liquid crystal composition R was prepared according to a conventional method. Isoquinoline was added to the obtained liquid crystal composition R at 1.0% by mass to prepare a liquid crystal composition M according to the present invention. As a comparative example, a liquid crystal composition R containing no isoquinoline was added.
And injecting the liquid crystal composition M according to the present invention into a TN cell having a 90 ° twist, charging time (sec), electro-optical characteristics, and voltage holding ratio.
(%) And phase transition temperature (° C.).
【0019】帯電時間測定方法 :Structure Probe, I
nc.製 Zerostat Antistatic Gun を使用してテストセル
を帯電させた。テストセルの電極部分が点灯してから消
灯までの時間をストップウォッチで測定した。 比抵抗測定方法 :液体電極に液晶組成物を入れ電圧
(DC)1V印加時の抵抗値を25℃にて測定した。 電圧保持率測定方法:セル厚 d=8.3μmの90°ツイストT
Nセルに5Vの電圧を印加した際、20msec後に保持されて
いる電圧を測定した。この値と初期電圧5Vとの比率を%
で表す。 閾値電圧測定方法 :90°ツイストTNセルに電圧を印加
し、初期の透過率を100%としたときの、90%透過率時の
電圧を測定した。 相転移温度(ネマチック−アイソトロピック相転移温度)
測定方法:温度を上昇させた際に液晶(ネマチック相)
がアイソトロピック相に変化するときの温度(℃)を目視
による観察で測定した。Charge time measurement method: Structure Probe, I
The test cell was charged using the nc. Zerostat Antistatic Gun. The time from when the electrode portion of the test cell turned on until when it turned off was measured with a stopwatch. Specific resistance measurement method: Put the liquid crystal composition in the liquid electrode and apply voltage
(DC) The resistance value when 1 V was applied was measured at 25 ° C. Voltage holding ratio measurement method: 90 ° twist T with cell thickness d = 8.3μm
When a voltage of 5 V was applied to the N cell, the voltage held after 20 msec was measured. The ratio of this value to the initial voltage of 5V is%
Expressed by Threshold voltage measurement method: A voltage was applied to a 90 ° twist TN cell, and the voltage at 90% transmittance was measured when the initial transmittance was 100%. Phase transition temperature (nematic-isotropic phase transition temperature)
Measurement method: Liquid crystal (nematic phase) when temperature is increased
The temperature (° C.) when was changed to the isotropic phase was measured by visual observation.
【0020】[0020]
【表1】 [Table 1]
【0021】本発明の液晶組成物であるMは、Rに比べて
帯電時間が1/6になり、帯電を防止する効果が大きいこ
とがわかる。一方、相転移温度や閾値電圧はほとんど変
化がないことがわかる。イソキノリン添加により、比抵
抗及び電圧保持率は低下するが、電気光学特性には影響
がなかった。このように本発明の方法は液晶組成物の電
気光学特性等をほとんど変えることなく、帯電抑制効果
があることがわかる。It can be seen that M, which is the liquid crystal composition of the present invention, has a charging time 1/6 that of R, and has a large effect of preventing charging. On the other hand, it can be seen that the phase transition temperature and the threshold voltage hardly change. The addition of isoquinoline reduced the specific resistance and the voltage holding ratio, but did not affect the electro-optical characteristics. As described above, it can be seen that the method of the present invention has the effect of suppressing charging without substantially changing the electro-optical characteristics and the like of the liquid crystal composition.
【0022】さらに液晶組成物M及びRをTNセルに注入し
た後、UV信頼性試験(図1)及び加熱信頼性試験(図2)を行
ったが、四級アンモニウム塩のようなイオン性物質を添
加した系で見られるような、初期比抵抗及び保持率の低
下が信頼性試験により更に悪化する現象は見られなかっ
た。すなわち、イソキノリン添加による信頼性の大幅な
悪化は認められなかった。このようにイソキノリンの添
加は従来のイオン性物質の添加に比べて極めて安定な液
晶組成物を提供することができるものである。Further, after injecting the liquid crystal compositions M and R into the TN cell, a UV reliability test (FIG. 1) and a heating reliability test (FIG. 2) were performed, and an ionic substance such as a quaternary ammonium salt was tested. No decrease in the initial specific resistance and the retention as seen in the system to which was added was further deteriorated by the reliability test. That is, no significant deterioration in reliability due to the addition of isoquinoline was observed. As described above, the addition of isoquinoline can provide a liquid crystal composition which is extremely stable as compared with the conventional addition of an ionic substance.
【0023】[0023]
【発明の効果】本発明のイソキノリンを添加した液晶組
成物により、液晶組成物の本来の特性を損ねることなく
帯電現象が抑制された液晶組成物を得ることができた。
また、この組成物を用いて、帯電抑制効果に優れた液晶
表示素子を作成することができた。この液晶組成物はTN
及びSTN-LCD(STN 液晶ディスプレイ)として有用かつ実
用的である。本発明の方法に従えば、液晶組成によらず
帯電防止効果を得ることができる。本発明による液晶組
成物を使用すれば、製造工程での帯電による誤表示や、
工程に特別な除電設備を設けることが必要なくなり、製
造工程の削減生産性の向上が図れる。According to the liquid crystal composition to which the isoquinoline of the present invention is added, a liquid crystal composition in which the charging phenomenon is suppressed without impairing the original characteristics of the liquid crystal composition can be obtained.
In addition, a liquid crystal display device having an excellent charge suppressing effect was able to be produced using this composition. This liquid crystal composition is TN
And it is useful and practical as STN-LCD (STN liquid crystal display). According to the method of the present invention, an antistatic effect can be obtained regardless of the liquid crystal composition. If the liquid crystal composition according to the present invention is used, erroneous display due to electrification in the manufacturing process,
It is not necessary to provide a special static elimination facility in the process, and the production process can be reduced and the productivity can be improved.
【図1】イソキノリン添加液晶のUV信頼性試験のグラフFIG. 1 is a graph of a UV reliability test of a liquid crystal containing isoquinoline.
【図2】イソキノリン添加液晶の加熱信頼性試験のグラ
フFIG. 2 is a graph of a heating reliability test of the liquid crystal containing isoquinoline.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 加藤 直枝 東京都葛飾区青戸7−24−1−403 (72)発明者 高津 晴義 東京都東大和市仲原3−6−27 Fターム(参考) 4H027 BA01 BB04 BC04 BD24 BE07 CL01 CL04 CR01 CS04 CT02 CT04 CU01 CW02 DL01 DL02 ──────────────────────────────────────────────────続 き Continuation of the front page (72) Inventor Naoe Kato 7-24-1-403 Aoto, Katsushika-ku, Tokyo (72) Inventor Haruyoshi Takatsu 3-6-27 Nakahara, Higashiyamato-shi, Tokyo F-term (reference) 4H027 BA01 BB04 BC04 BD24 BE07 CL01 CL04 CR01 CS04 CT02 CT04 CU01 CW02 DL01 DL02
Claims (6)
する液晶組成物であって、式(1)で示されるイソキノリ
ン若しくはイソキノリン構造を有する化合物、式(2)で
示されるキナルジン若しくはキナルジン構造を有する化
合物、式(3)で示されるキノキサリン若しくはキノキサ
リン構造を有する化合物のいずれか一つ若しくはその任
意の組み合わせである成分Aを含有することを特徴とす
るネマチック液晶組成物。 【化1】 1. A liquid crystal composition having a specific resistance of at least 1.0 × 10 11 Ωcm, comprising an isoquinoline represented by the formula (1) or a compound having an isoquinoline structure, a quinaldine represented by the formula (2) or a quinaldine structure represented by the formula (2): 1. A nematic liquid crystal composition comprising: a compound having a quinoxaline represented by the formula (3) or a compound having a quinoxaline structure, or a component A which is an arbitrary combination thereof. Embedded image
ことを特徴とする請求項1記載の液晶組成物。2. The liquid crystal composition according to claim 1, wherein the content of the component A is 0.01 to 10.0% by mass.
する請求項1または2記載の液晶組成物。3. The liquid crystal composition according to claim 1, wherein the charging time is 30 seconds or less.
徴とする請求項1または2記載の液晶組成物。4. The liquid crystal composition according to claim 1, wherein the voltage holding ratio is from 70% to 85%.
た液晶表示素子。5. A liquid crystal display device using the liquid crystal composition according to claim 1.
って、請求項1から3記載の液晶組成物を液晶表示素子に
使用することを特徴とする方法。6. A method for improving charging of a liquid crystal display device, wherein the liquid crystal composition according to claim 1 is used for a liquid crystal display device.
Priority Applications (1)
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JP2000133403A JP2001316670A (en) | 2000-05-02 | 2000-05-02 | Liquid crystal composition |
Applications Claiming Priority (1)
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JP2000133403A JP2001316670A (en) | 2000-05-02 | 2000-05-02 | Liquid crystal composition |
Publications (1)
Publication Number | Publication Date |
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JP2001316670A true JP2001316670A (en) | 2001-11-16 |
Family
ID=18641908
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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WO2005042670A1 (en) * | 2003-10-30 | 2005-05-12 | Dainippon Ink And Chemicals, Inc. | Nematic liquid crystal composition and liquid crystal display device using same |
JP2005154745A (en) * | 2003-10-30 | 2005-06-16 | Dainippon Ink & Chem Inc | Nematic liquid crystal composition and liquid crystal element given by using the same |
JP2006016586A (en) * | 2003-10-30 | 2006-01-19 | Dainippon Ink & Chem Inc | Nematic liquid crystal composition and liquid crystal display device using the same |
KR101060207B1 (en) | 2003-10-30 | 2011-08-29 | 디아이씨 가부시끼가이샤 | Nematic liquid crystal composition and liquid crystal display element using the same |
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