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JPH0668082B2 - Blue filter for liquid crystal display - Google Patents
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JPH0668082B2 - Blue filter for liquid crystal display - Google Patents

Blue filter for liquid crystal display

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Publication number
JPH0668082B2
JPH0668082B2 JP61038305A JP3830586A JPH0668082B2 JP H0668082 B2 JPH0668082 B2 JP H0668082B2 JP 61038305 A JP61038305 A JP 61038305A JP 3830586 A JP3830586 A JP 3830586A JP H0668082 B2 JPH0668082 B2 JP H0668082B2
Authority
JP
Japan
Prior art keywords
dye
liquid crystal
parts
crystal display
blue filter
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.)
Expired - Lifetime
Application number
JP61038305A
Other languages
Japanese (ja)
Other versions
JPS62197459A (en
Inventor
尚登 伊藤
民雄 三小田
宏 相賀
昭夫 唐沢
Original Assignee
三井東圧化学株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 三井東圧化学株式会社 filed Critical 三井東圧化学株式会社
Priority to JP61038305A priority Critical patent/JPH0668082B2/en
Publication of JPS62197459A publication Critical patent/JPS62197459A/en
Publication of JPH0668082B2 publication Critical patent/JPH0668082B2/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Description

【発明の詳細な説明】 〔産業上の利用分野〕 本発明は液晶表示用青色フィルターに関する。The present invention relates to a blue filter for liquid crystal display.

〔従来の技術〕[Conventional technology]

現在、液晶表示用フイルターの多くはゼラチン類を基材
としているため、耐久性が充分でなかった。そこで基材
として、耐久性の良好な樹脂あるいは無機の透明な物質
の利用が検討されている。(特開昭59−127036) 〔発明が解決しようとする問題点〕 樹脂あるいは無機物質の透明着色材としては、油溶性染
料あるいは、分散染料が知られている。(染料便覧 丸
善刊) しかしこれらの色素の中では、充分な着色性,耐久性
(特に耐光,耐熱性)を有し、かつ分光特性に優れた色
素がなかった。
At present, most of the filters for liquid crystal display use gelatins as a base material, so that the durability is not sufficient. Therefore, the use of a highly durable resin or an inorganic transparent substance as a base material has been studied. (JP-A-59-127036) [Problems to be solved by the invention] Oil-soluble dyes or disperse dyes are known as transparent colorants of resins or inorganic substances. (Handbook of dyes, published by Maruzen) However, none of these dyes has sufficient coloring properties and durability (particularly light resistance and heat resistance) and has excellent spectral characteristics.

又、新しいフイルターの製造方法として検討されている
昇華蒸着法(特開昭59−127036)などの方法に適する色
素もなかった。
Further, there was no dye suitable for the sublimation vapor deposition method (Japanese Patent Laid-Open No. 59-127036) which has been studied as a new method for producing a filter.

〔問題を解決するための手段〕[Means for solving problems]

本発明者らは鋭意検討の結果、耐光、耐熱性のよい色素
を見出し、更にこの色素を含有する液晶表示用フィルタ
ーが優れた性能を持つことを見出し、本発明を完成し
た。
As a result of intensive studies, the inventors of the present invention found a dye having good light resistance and heat resistance, and further found that a filter for liquid crystal display containing the dye has excellent performance, and completed the present invention.

即ち、本発明は下式(I) 〔式(I)中XとYは、ニトロ基又はヒドロキシ基を表
わし、R1とR5はアルキル基、シクロアルキル基を表わ
し、R2,R3及びR4は水素原子又はアルキル基を表わ
す。〕で示される色素を含有する液晶表示用青色フィル
ターに関する。
That is, the present invention provides the following formula (I) [In the formula (I), X and Y represent a nitro group or a hydroxy group, R 1 and R 5 represent an alkyl group or a cycloalkyl group, and R 2 , R 3 and R 4 represent a hydrogen atom or an alkyl group. . ] It is related with the blue filter for liquid crystal displays containing the dye shown by these.

本発明の色素は、ジニトロ−ジヒドロキシアントラキノ
ン又はテトラヒドロキシアントラキノン及びそのロイコ
体とアニリン誘導体を反応させることにより得られる。
The dye of the present invention can be obtained by reacting dinitro-dihydroxyanthraquinone or tetrahydroxyanthraquinone or a leuco derivative thereof with an aniline derivative.

又、この色素を用いて、着色する基材としては、ポリエ
ステル樹脂、アクリル樹脂、ポリイミド樹脂、ポリメチ
ルメタアクリレート樹脂、アルミナ膜などが挙げられ、
その着色方法は練り込み,転写,染色,昇華蒸着などが
ある。
In addition, examples of the base material to be colored using this dye include polyester resin, acrylic resin, polyimide resin, polymethylmethacrylate resin, and alumina film,
The coloring method includes kneading, transfer, dyeing, and sublimation vapor deposition.

又、R1〜R5で表わされるアルキル基としては、炭素数1
〜20の直鎖、又は分岐のアルキル基を意味し、シクロア
ルキル基としてはシクロヘキシル基等を意味する。
The alkyl group represented by R 1 to R 5 has 1 carbon atom
To 20 linear or branched alkyl groups, and cycloalkyl groups include cyclohexyl groups and the like.

〔発明の効果〕〔The invention's effect〕

本発明により、充分な着色性、耐久性(耐光、耐熱性)
を有し、かつ分光性に優れた色素を得ることができた。
Sufficient colorability and durability (light resistance, heat resistance) according to the present invention
It was possible to obtain a dye having the above-mentioned properties and having excellent spectral properties.

本発明フイルター用青色色素の式(I)の性能は、次の
表−1の様であった。
The performance of formula (I) of the blue dye for the filter of the present invention was as shown in Table 1 below.

1)着色性 PET(ポリエチレンテレフタレート):フイルムと色素
原体とエチレングリコールを入れ、130℃にて1時間染
色した時の着色性 PS(ポリスチレン):樹脂と色素を混合し成型した時の
着色性 Al:アルミナゲルをガラスに塗布,焼成し、得た基材
(γ−アルミナ)に色素を転写した時の着色性 2)耐熱性 着色をした各基材(PET,PS,Al)での大気中180℃で4時
間加熱後の透過スペクトル変化量が 変化なし ◎ 10%以下 ○ 30%以内 △ 30%以上 × 3)耐光性 着色をした各基材(PET,PS,Al)のフエードメーター20
時間後のスペクトル変化量が 変化なし ◎ 10%以下 ○ 30%以内 △ 30%以上 × 4)昇華性 大気圧下、200℃以上で昇華する場合を○、昇華しない
時を×とした。
1) Colorability PET (polyethylene terephthalate): Colorability when film, dye base and ethylene glycol are put and dyed for 1 hour at 130 ° C PS (polystyrene): Colorability when resin and dye are mixed and molded Al: Alumina gel is applied to glass and baked, and the coloring property when the dye is transferred to the obtained base material (γ-alumina) 2) Heat resistance Atmosphere in each colored base material (PET, PS, Al) No change in transmission spectrum change after heating at 180 ° C for 4 hours ◎ 10% or less ○ Within 30% △ 30% or more × 3) Light resistance Fade meter of each colored substrate (PET, PS, Al) 20
No change in spectral change after time ◎ 10% or less ○ Within 30% △ 30% or more × 4) Sublimation property ○ When sublimation occurs at 200 ° C or higher under atmospheric pressure, it is evaluated as ○, and when not sublimated.

5)フイルター性能 540nmの透過率が5%以下となる様な濃度で着色した基
材の460nmの透過率が55%以上なら○、55%以下なら× 〔実施例〕 以下、実施例にて、本発明を詳しく説明する。ただし、
「部」は重量部を表す。
5) Filter performance ○ If the transmittance at 460 nm of the substrate colored at a concentration such that the transmittance at 540 nm is 5% or less is 55% or more, and if it is 55% or less ×, [Example] In the following examples, The present invention will be described in detail. However,
"Parts" represent parts by weight.

〔実施例−1〕 表−1中、染料番号12の色素10部を、ポリプロピレング
リコール100部と混合し、微粒子化後、紙の塗布,乾燥
し転写紙をつくり、アルミナゲルを塗布,焼成した厚さ
3mmのガラス板に200℃にて転写し、青色フイルターをつ
くった。このフイルターの分光特性(透過性)を分光光
度計で測定したチヤートを図−1に示す。
[Example-1] In Table-1, 10 parts of the dye of Dye No. 12 was mixed with 100 parts of polypropylene glycol, and after atomization, paper was applied and dried to form transfer paper, and alumina gel was applied and baked. thickness
Transfer to a 3mm glass plate at 200 ° C to make a blue filter. Fig. 1 shows a chart obtained by measuring the spectral characteristics (transmittance) of this filter with a spectrophotometer.

染料番号12の色素の合成は下記にて行なった。The dye No. 12 was synthesized below.

ロイコ1,4,5,8−テトラヒドロキシアントラキノン18.8
部、n−ヘキサノール200部、ホウ酸1部、亜鉛1部と
2,6−ジメチルアニリン40部を混合し、150℃4時間反応
した。反応生成物を別後、ニトロベンゼン100部とピ
ペリジン1部と共に、150℃1時間加熱処理した。
Leuco 1,4,5,8-tetrahydroxyanthraquinone 18.8
Parts, n-hexanol 200 parts, boric acid 1 part, zinc 1 part
40 parts of 2,6-dimethylaniline were mixed and reacted at 150 ° C. for 4 hours. After separating the reaction product, it was heat treated with 100 parts of nitrobenzene and 1 part of piperidine at 150 ° C. for 1 hour.

ニトロベンゼンを水蒸気蒸溜で留去後、カラムにて分離
し、下記色素10部を得た。
After distilling off nitrobenzene by steam distillation, it was separated on a column to obtain 10 parts of the following dye.

λmax(クロロホルム中)625,575nm IR(cm-1)2950,1600,1570,1480,1450,1170 NMR(ppm)2.18(s,6H)、6.7(d,1H)、7.1〜7.5(6
H) 〔実施例−2〕 ポリエステルフイルム10部、エチレングリコール2000部
と表−1中染料番号2の色素2部を入れ、130℃1時間
で染色し、青色フイルターをつくった。
λmax (in chloroform) 625,575nm IR (cm -1 ) 2950,1600,1570,1480,1450,1170 NMR (ppm) 2.18 (s, 6H), 6.7 (d, 1H), 7.1 to 7.5 (6
H) [Example-2] 10 parts of polyester film, 2000 parts of ethylene glycol and 2 parts of dye No. 2 in Table-1 were added and dyed at 130 ° C for 1 hour to prepare a blue filter.

このフイルターの分光特性(透過率)を分光光度計で測
定したチヤートを図−2に示す。
The chart obtained by measuring the spectral characteristics (transmittance) of this filter with a spectrophotometer is shown in FIG.

染料番号2の色素の合成は下記にて行なった。The dye No. 2 was synthesized as follows.

1,5−ジヒドロキシ−4,8−ジニトロアントラキノン33
部、2,6−ジエチルアニリン75部とo−ジクロルベンゼ
ン1000部を混合し、170℃15時間反応した。n−ジクロ
ルベンゼンを水蒸気蒸留にて留去した。カラムにて分離
し、下記の色素を10部得た。
1,5-dihydroxy-4,8-dinitroanthraquinone 33
Parts, 75 parts of 2,6-diethylaniline and 1000 parts of o-dichlorobenzene were mixed and reacted at 170 ° C. for 15 hours. n-Dichlorobenzene was distilled off by steam distillation. Separation on a column gave 10 parts of the following dyes.

λmax(クロロホルム中)625,575nm m.p.260.2〜264.8℃ IR(cm-1)2970,1590,1210,1160 NMR(ppm)1.1(t,6H)、2.5(q,4H)、6.75(d,1H)、
7.1〜7.5(5H)、7.9(d,1H) 分子量432 〔実施例−3〕 ポリメチルメタアクリレート樹脂板に、表中9の色素1
部とパイロナールMD−1200(東洋紡績社製品)10部とシ
リカゲル1部より調製,作製した転写紙(フイルター用
に色素を配置)をのせ、200℃でカレンダーを通したと
ころ、青色のフイルターが得られた。
λmax (in chloroform) 625,575nm mp 260.2-264.8 ℃ IR (cm -1 ) 2970,1590,1210,1160 NMR (ppm) 1.1 (t, 6H), 2.5 (q, 4H), 6.75 (d, 1H),
7.1 ~ 7.5 (5H), 7.9 (d, 1H) Molecular weight 432 [Example-3] Dye 1 of 9 in the table on a polymethylmethacrylate resin plate
Part and Pyronal MD-1200 (product of Toyobo Co., Ltd.) and 1 part of silica gel prepared and prepared, and a transfer paper (pigment is arranged for the filter) is placed on the paper and passed through a calendar at 200 ° C to obtain a blue filter. Was given.

このフイルターの分光特性(透過率)を分光光度計で測
定したチヤートを図−3に示す。
A chart obtained by measuring the spectral characteristics (transmittance) of this filter with a spectrophotometer is shown in FIG.

染料番号9の色素の合成は、実施例1及び2と同様に行
った。
The dye No. 9 was synthesized in the same manner as in Examples 1 and 2.

〔実施例−4〕 実施例1〜3の方法に準じて一般式(I)で示される表
−2の色素をフイルターとした時、フイルターとしての
性能が良好であった。
[Example 4] When the dye of Table 2 represented by the general formula (I) was used as a filter according to the method of Examples 1 to 3, the performance as a filter was good.

【図面の簡単な説明】[Brief description of drawings]

図−1,−2,及び図−3は本発明に係る色素を用いて、実
施例−1,−2,及び実施例−3にて作製したフイルターの
各波長での分光光度計での透過率を示す図である。
FIGS. 1, -2, and 3 show the transmission of each of the filters produced in Examples 1, -2, and Example-3 in the spectrophotometer at each wavelength using the dye according to the present invention. It is a figure which shows a rate.

Claims (1)

【特許請求の範囲】[Claims] 【請求項1】下記一般式(I) 〔一般式(I)中、XとYは、ニトロ基、又はヒドロキ
シ基を表わし、R1とR5はアルキル基、シクロアルキル基
を表わし、R2,R3及びR4は、水素原子又はアルキル基を
表わす。〕 で表わされる色素を含有する液晶表示用青色フィルタ
ー。
1. The following general formula (I): [In the general formula (I), X and Y represent a nitro group or a hydroxy group, R 1 and R 5 represent an alkyl group or a cycloalkyl group, and R 2 , R 3 and R 4 represent a hydrogen atom or Represents an alkyl group. ] A blue filter for liquid crystal display containing a dye represented by
JP61038305A 1986-02-25 1986-02-25 Blue filter for liquid crystal display Expired - Lifetime JPH0668082B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP61038305A JPH0668082B2 (en) 1986-02-25 1986-02-25 Blue filter for liquid crystal display

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP61038305A JPH0668082B2 (en) 1986-02-25 1986-02-25 Blue filter for liquid crystal display

Publications (2)

Publication Number Publication Date
JPS62197459A JPS62197459A (en) 1987-09-01
JPH0668082B2 true JPH0668082B2 (en) 1994-08-31

Family

ID=12521585

Family Applications (1)

Application Number Title Priority Date Filing Date
JP61038305A Expired - Lifetime JPH0668082B2 (en) 1986-02-25 1986-02-25 Blue filter for liquid crystal display

Country Status (1)

Country Link
JP (1) JPH0668082B2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5608091A (en) * 1993-12-28 1997-03-04 Nippon Shokubai Co., Ltd. Quinizarin compound, method for production thereof, and use therefor
DE69421122T2 (en) * 1993-07-09 2000-01-20 Mitsui Chemicals, Inc. New dyes and their use

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3362966A (en) 1963-09-05 1968-01-09 Interchem Corp Substituted 1, 5-dihydroxy-4-anilino-8-nitro-anthraquinone dyes for polypropylene

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5125335B2 (en) * 1972-04-13 1976-07-30
JPS5790079A (en) * 1980-11-26 1982-06-04 Canon Inc Liquid crystal display device

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3362966A (en) 1963-09-05 1968-01-09 Interchem Corp Substituted 1, 5-dihydroxy-4-anilino-8-nitro-anthraquinone dyes for polypropylene

Also Published As

Publication number Publication date
JPS62197459A (en) 1987-09-01

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