JPS62220578A - Liquid crystal composition and multi-color liquid crystal display element - Google Patents
Liquid crystal composition and multi-color liquid crystal display elementInfo
- Publication number
- JPS62220578A JPS62220578A JP6391886A JP6391886A JPS62220578A JP S62220578 A JPS62220578 A JP S62220578A JP 6391886 A JP6391886 A JP 6391886A JP 6391886 A JP6391886 A JP 6391886A JP S62220578 A JPS62220578 A JP S62220578A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- compound
- light
- luminescent
- absorbance
- 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 37
- 239000000203 mixture Substances 0.000 title claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 238000002835 absorbance Methods 0.000 claims abstract description 12
- 238000004020 luminiscence type Methods 0.000 claims description 11
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 claims description 6
- 239000000975 dye Substances 0.000 description 35
- 210000004027 cell Anatomy 0.000 description 13
- 230000005284 excitation Effects 0.000 description 11
- 238000000034 method Methods 0.000 description 6
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 4
- 229940125961 compound 24 Drugs 0.000 description 4
- OFYAEKMIQIIUAT-UHFFFAOYSA-N 4-cyclohexylbenzonitrile Chemical compound C1=CC(C#N)=CC=C1C1CCCCC1 OFYAEKMIQIIUAT-UHFFFAOYSA-N 0.000 description 2
- 229940126639 Compound 33 Drugs 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 description 2
- 230000003098 cholesteric effect Effects 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 1
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- -1 1,6-bis (p -ethylphenyl) -1,3,5-hexatriene Chemical compound 0.000 description 1
- BOBLSBAZCVBABY-WPWUJOAOSA-N 1,6-diphenylhexatriene Chemical compound C=1C=CC=CC=1\C=C\C=C\C=C\C1=CC=CC=C1 BOBLSBAZCVBABY-WPWUJOAOSA-N 0.000 description 1
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 description 1
- BPMBNLJJRKCCRT-UHFFFAOYSA-N 4-phenylbenzonitrile Chemical group C1=CC(C#N)=CC=C1C1=CC=CC=C1 BPMBNLJJRKCCRT-UHFFFAOYSA-N 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- 229940126657 Compound 17 Drugs 0.000 description 1
- 241001474791 Proboscis Species 0.000 description 1
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 1
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol group Chemical group [C@@H]1(CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)[C@H](C)CCCC(C)C HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 229940126208 compound 22 Drugs 0.000 description 1
- 229940127204 compound 29 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- WSFMFXQNYPNYGG-UHFFFAOYSA-M dimethyl-octadecyl-(3-trimethoxysilylpropyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCC[Si](OC)(OC)OC WSFMFXQNYPNYGG-UHFFFAOYSA-M 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Abstract
Description
【発明の詳細な説明】
「産業上の利用分野」
本発明は、電圧印加による液晶分子の配向変化を利用し
、発光色をコントロールして表示を行うマルチカラー表
示に関するものである。DETAILED DESCRIPTION OF THE INVENTION "Field of Industrial Application" The present invention relates to a multi-color display that controls the color of emitted light by utilizing changes in the orientation of liquid crystal molecules due to the application of voltage.
「従来の技術」
近年、省エネルギーおよび小型化の観点から液晶表示素
子が広く使用されるようになった。液晶の電気光学効果
には、ねじれネマチ、り（ＴＮ）型電界効果を利用した
ものが最も一般的に用いられており、その他、動的散乱
効果（ＤＳＭ ）、ｒスト−ホスト効果（ＧＨ）、相転
移効果（ＰＴ）等が利用されている。これらの表示方法
は消費電力が小さいことや外周光による、いわゆるウォ
ッシュアウト現象がないこと等の長所を有してのる。"Prior Art" In recent years, liquid crystal display elements have come into wide use from the viewpoint of energy saving and miniaturization. The most commonly used electro-optical effects in liquid crystals are twisted nematic and TN (TN) field effects, and others include dynamic scattering effect (DSM) and r-sthost effect (GH). , phase transition effect (PT), etc. are utilized. These display methods have advantages such as low power consumption and no so-called washout phenomenon caused by peripheral light.
しかし、表示に輝きがなく精彩を欠く点や視艶が狭い点
等の欠点のうちいずれかを有している。However, they have some drawbacks, such as lackluster display and poor visual gloss.
一方、この欠点を克服するため発光型表示方法もいくつ
か提案されている。例えば、ＧＨ効果のダスト分子とし
て螢光性二色性分子を用いたもの（ＲｓＤ＊Ｌａｒｒｂ
ｅｓ＋ ｇ ＲＣＡ、Ｒｅｖ、 Ｖｏｌ ５４ ｓ ｐ
３２９ ＋ １９７３年や特開昭５４−４８６９０）
、コレステリック−ネマチックＰＴモードに螢光性希土
類キレート化合物を加えたもの（Ｌ、Ｊ’、ＹｕらＡｐ
ｐｌ、Ｐｈｙｓ、Ｌｅｔｔ。On the other hand, several light-emitting display methods have been proposed to overcome this drawback. For example, a method using a fluorescent dichroic molecule as a dust molecule for the GH effect (RsD*Larrb
es+ g RCA, Rev, Vol 54 sp
329 + 1973 and Japanese Unexamined Patent Publication No. 54-48690)
, cholesteric-nematic PT mode with addition of fluorescent rare earth chelate compound (L, J', Yu et al. Ap
pl, Phys, Lett.
Ｖｏ １３１ ｅ ｐ ７１９ ｅ １９７７ 年）、
Ｔ Ｎ ｆｆ１ｆｉ示Ｘ子ｃ７）背面にアクリル螢光板
を設置したもの（Ｇ、Ｂａｕｒら Ａｐｐｌ、Ｐｈｙｏ
、Ｌｅｔｌ、 Ｖｏｌ ３１ ｅ ｐ ４ ｔ １９７
７年や特開昭５６−１２５７７２および特開昭５６−１
２５７２１）等がある。しかしながら、これらの表示方
法にはコントラストの低さ、素子厚みの増加、またはマ
ルチカラー表示が困難である点等の欠点が含まれている
。Vo 131 e p 719 e 1977),
T N ff1fi indicator
, Letl, Vol 31 e p 4 t 197
7 years, JP-A-56-125772 and JP-A-56-1
25721) etc. However, these display methods include drawbacks such as low contrast, increased device thickness, or difficulty in multicolor display.
［発明が解決しようとする問題点］
本発明者等は上記に鑑み、コントラストの高いマルチカ
ラー表示用の発光型液晶表示素子を得るべく鋭意検討の
結果、液晶組成の発光性化合物として二色性の大きな発
光性色素と等方向つまり二色性の小さな発光性色素を同
時にダスト化合物としてホスト液晶に添加した組成物を
、従来から通常使用されて−る平行配向処理した表示セ
ル中に封入した素子を開発することによシ従来完成され
得なかった高性能表示方法を実現させ本発明を完成させ
るに至った。[Problems to be Solved by the Invention] In view of the above, the inventors of the present invention have made intensive studies to obtain a light-emitting liquid crystal display element for multi-color display with high contrast, and have found that a dichroic compound can be used as a light-emitting compound in the liquid crystal composition. A device in which a composition in which a large luminescent dye and a small isotropically dichroic luminescent dye are simultaneously added as a dust compound to a host liquid crystal is enclosed in a display cell that has been subjected to parallel alignment treatment, which has been commonly used in the past. By developing this, we have realized a high-performance display method that could not be completed in the past, and completed the present invention.
［問題点を解決するための手段」
即ち、本発明は分子軸方向の吸光度または発光強度と分
子軸だ垂直な方向の吸光度または発光強度の比で定義さ
れる二色比が５以上の発光性化合物と２以下の発光性化
合物を含有せるネマチックまたはコレステリック液晶組
成物である。[Means for Solving the Problems] That is, the present invention provides a luminescent material with a dichroic ratio of 5 or more defined as the ratio of absorbance or luminescence intensity in the direction of the molecular axis to absorbance or luminescence intensity in the direction perpendicular to the molecular axis. It is a nematic or cholesteric liquid crystal composition containing a compound and two or less luminescent compounds.
更に、本発明は分子軸方向の吸光度また′ｆｉ伯光強光
強度分子軸に画直な方向の吸光度または発光強度の比で
定義される二色比が５以上の発光性化合物と２以下の発
光性化合物を含有せるネマチ、りまたはコレステリック
液晶組成物な封入せるマルチカラー液晶表示素子である
。Furthermore, the present invention provides a luminescent compound with a dichroic ratio defined by the absorbance in the direction of the molecular axis or the ratio of the absorbance or luminescence intensity in the direction perpendicular to the molecular axis, and the dichroic ratio of 5 or more and the light intensity of 2 or less. This is a multicolor liquid crystal display element in which a nematic, cholesteric, or cholesteric liquid crystal composition containing a luminescent compound is encapsulated.
以下、本発明を更に詳細に説明する。The present invention will be explained in more detail below.
本発明においては紫外線等の励起光により発光する発光
性色素として分子軸方向の吸光度または発光強度と分子
軸に垂直な方向の吸光度または発光強度の比で定義され
る二色比が大きいものと小さいそれぞれ発光色の異なる
ものを組合せることによって励起光照射下垂直配向セル
を用いた場合電圧無印加時には、高二色性色素はセル面
と垂直配向を取り励起光を吸収しないため発光を行なわ
ないが、二色性の小さな等方向色素は励起光を吸収し発
生を呈するので、等方性色素の発光のみが認識されるが
、電圧を印加すると高二色性色素もセル面と平行になる
ため励起光を吸収し、発光を行なうようになり両者の発
光スペクトルの和として色彩が認識され、電圧ＯＮ −
ＯＦＦによる色彩の違いが生じる。In the present invention, as luminescent dyes that emit light with excitation light such as ultraviolet rays, those having a large dichroic ratio and those having a small dichroic ratio defined as the ratio of absorbance or emission intensity in the direction of the molecular axis to absorbance or emission intensity in the direction perpendicular to the molecular axis are used. When using a vertically aligned cell under excitation light irradiation by combining dyes with different emission colors, when no voltage is applied, the highly dichroic dyes are aligned perpendicular to the cell surface and do not absorb excitation light, so they do not emit light. , isotropic dyes with low dichroism absorb excitation light and exhibit emission, so only the emission of isotropic dyes is recognized, but when voltage is applied, highly dichroic dyes also become parallel to the cell surface and are excited. It absorbs light and emits light, and color is recognized as the sum of the emission spectra of both, and the voltage ON -
Differences in color occur due to OFF.
一方、平行配向セルを用いた場合には、電圧０８時とＯ
ＦＦ時の現象が垂直配向セルを用いた場合と逆になるだ
けで全く同じ原理で発光色の変化が生じる。このような
原理を利用することによりコントラストの高いマルチカ
ラー表示を実現しようとするものであるから、一方の二
色比の値は大きい程良く、一定値以上であることを要し
、他方の二色比の値は１に近い程良く一定値以下である
ことが必要である。On the other hand, when a parallel alignment cell is used, the voltage is 08 o'clock and O
The change in luminescent color occurs on exactly the same principle, except that the phenomenon during FF is reversed to that when a vertically aligned cell is used. Since we are trying to realize a multi-color display with high contrast by utilizing such a principle, the larger the value of one dichroic ratio, the better, and it must be above a certain value. The closer the value of the color ratio is to 1, the better, and it is necessary that it be below a certain value.
従って、本発明におりては二色比が５以上と大きい発光
性色素と二色比が２以下と小さい発光性色素が組合せて
用いられる。この組み合わせの範囲を外れると充分なコ
ントラストが得られない。Therefore, in the present invention, a luminescent dye with a high dichroic ratio of 5 or more and a luminescent pigment with a small dichroic ratio of 2 or less are used in combination. If the combination falls outside of this range, sufficient contrast cannot be obtained.
より好ましくは二色比６以上と１．５以下の組み合わせ
である。なお、ここにおいて発光とは螢光またけ燐光を
示すものである。More preferred is a combination of a dichroic ratio of 6 or more and 1.5 or less. Note that the term "light emission" here refers to fluorescence and phosphorescence.
本発明に用いられる二色比の大きい発光性色素は通常用
いられる発光性色素のうち二色比が５以上のものであれ
ば特に限定されないが例えば以下の化合物である。二色
比が５未満のものはコントラストの面で満足で泗ず、実
用的な使用に不充分である。The luminescent dye with a high dichroic ratio used in the present invention is not particularly limited as long as it is a commonly used luminescent dye with a dichroic ratio of 5 or more, but examples thereof include the following compounds. A dichroic ratio of less than 5 is unsatisfactory in terms of contrast and is insufficient for practical use.
Ｉ
化合物１
Ｃ２■５
化合物２
化合物４
化合物５
化合′吻７
化合物８
化合物９
化合物１０
化合物１１
化合物１２
化合物１３
化合物１４
化合物１５
化合物１６
化合物１７
化合物１８
化合物１９
化合物２０
本発明に用いられる二色比の小さい発光性色素は通常用
いられる発光性色素のうち二色比が２以下のものであれ
ば特に限定されないが例えば以下の化合物である。二色
比が２を越えるものは、ホストの配向に依存してしまい
コントラストが不鮮明となり現実的には使用できない。I Compound 1 C2■5 Compound 2 Compound 4 Compound 5 Compound's proboscis 7 Compound 8 Compound 9 Compound 10 Compound 11 Compound 12 Compound 13 Compound 14 Compound 15 Compound 16 Compound 17 Compound 18 Compound 19 Compound 20 Dichroic ratio used in the present invention Luminescent dyes with a small luminescent color are not particularly limited as long as they have a dichroic ratio of 2 or less among commonly used luminescent dyes, but examples include the following compounds. If the dichroic ratio exceeds 2, it depends on the orientation of the host, resulting in unclear contrast and cannot be used practically.
化合物２２
化合物２４
化合物２８
化合物２９
化合物３０
化＆物３１
ＯＨＯ
化合物３２
本発明においては、上記の如き発光性色素を夫夫一種ず
つ使用してもよく、また二種以上混合して使用すること
もできる。Compound 22 Compound 24 Compound 28 Compound 29 Compound 30 Chemical & Mono 31 OHO Compound 32 In the present invention, the above-mentioned luminescent dyes may be used one by one, or two or more types may be used as a mixture. can.
本発明に使用されるネマチック液晶としては、４−シア
ノビフェニル系液晶混合、物（例えば、メルク社商品記
号Ｅ−８）、４−シアノフェニルシクロヘキサン系等の
液晶混合物（例えばメルク社商品記号ＺＬＩ −１８４
０）、４−ンアノピシクロ゛ヘキサン系液晶混合物（例
えば、メルク社商品記号ＺＬＩ ２８０６ ）等があり
、その他、７ツフペース系、アゾキシ系、ピフェニル系
、エステル系、ピリジン系、テトラシン系等の液晶も単
体または混合物として使用できる。Examples of the nematic liquid crystal used in the present invention include 4-cyanobiphenyl liquid crystal mixtures (for example, Merck's product symbol E-8), and 4-cyanophenylcyclohexane liquid crystal mixtures (for example, Merck's product symbol ZLI- 184
0), 4-anopycyclohexane-based liquid crystal mixtures (for example, Merck & Co., Ltd. product code: ZLI 2806), and other single liquid crystals such as 7-paste-based, azoxy-based, piphenyl-based, ester-based, pyridine-based, and tetracine-based liquid crystals. or can be used as a mixture.
・本発明においては！更に液晶混合体にコレステリルノ
ナエートまたは旋光性４−シアノ−４７−イソインチル
ビフェニル等の光学活性物質を加えた、電界無印加状態
ではコレステリ、、り相であり、電界印加状態でネマチ
ック相状態に相転移するコレステリ、り液晶混合体、い
わゆるカイラルネマチ、り液晶混合体を使用することも
できる。・In the present invention! Furthermore, when an optically active substance such as cholesteryl nonaate or optically active 4-cyano-47-isothylphenyl biphenyl is added to the liquid crystal mixture, it is in a cholesteric phase when no electric field is applied, and becomes a nematic phase when an electric field is applied. It is also possible to use cholesteric liquid crystal mixtures, so-called chiral nematic liquid crystal mixtures, which undergo a phase transition.
本発明においては、上記発光色素を上記液晶中に使用す
るに際しての色素濃度は、色素が液晶に溶解する限度内
にあって、且つ、二色性の色素分子が液晶分子の配向に
よって充分配向統制される範囲内であればよいが、一般
的には液晶に対し０．０１〜１０重を憾の濃度、好まし
くは０．０１〜３重−１を憾の濃度で使用するのが良い
。In the present invention, when the luminescent dye is used in the liquid crystal, the concentration of the dye is within the limit for dissolving the dye in the liquid crystal, and the dichroic dye molecules are sufficiently aligned by the alignment of the liquid crystal molecules. Generally, it is preferable to use a concentration of 0.01 to 10 times the liquid crystal, preferably 0.01 to 3 times the liquid crystal.
色素の液晶への溶解は、所定量を液晶と混合し、長時間
かき混ぜるか若しくは液晶が等方性液体となる温度以上
に加熱し、かき混ぜることによって行われ、所望の発光
カラー表示用液晶組成物とすることができる。The dye is dissolved in the liquid crystal by mixing a predetermined amount with the liquid crystal and stirring for a long time, or by heating the liquid crystal to a temperature higher than that at which it becomes an isotropic liquid and stirring, thereby producing the desired liquid crystal composition for luminescent color display. It can be done.
「実施例」
以下、実施例により本発明を表示方式とその動作原理に
ついて説明する。なお、実施例中、「部」は「重量部」
を示す。``Example'' The present invention will be described below with reference to an example regarding a display method and its operating principle. In addition, in the examples, "parts" are "parts by weight"
shows.
実施例１
４−シアノビシクロ系液晶混合物（メルク社商品記号Ｚ
ＬＩ−２８０６）中に青色の発光色素１，６−ビス（ｐ
−エチルフェニル） −１，３，５−ヘキサトリエン（
化合物８）を０．１部、赤色の発光色素Ｅｕ（ＢＦＡ）
５ （化合物３３）０．５部′？：溶解させた組成物
を式
％式％（３
で示される化合物（略号ＤＭＯＡＰ ）で垂直配向処理
した第１図に示す表示セル内に封入した。Example 1 4-cyanobicyclo liquid crystal mixture (Merck product code Z)
A blue luminescent dye 1,6-bis (p
-ethylphenyl) -1,3,5-hexatriene (
0.1 part of compound 8), red luminescent dye Eu (BFA)
5 (Compound 33) 0.5 part'? : The dissolved composition was sealed in a display cell shown in FIG. 1 which had been vertically aligned with a compound represented by the formula % (abbreviation DMOAP).
この状態でセル背面から３６６ ｎｍの励起光を照射す
ると表示素子は赤色の鮮やかな発光色を呈する。これは
第２図に示すように等方的発光体であるＥｕ （ＢＦＡ
）ｓ からの発光が主であるからである。In this state, when 366 nm excitation light is irradiated from the back of the cell, the display element emits bright red light. As shown in Figure 2, this is an isotropic light emitter Eu (BFA
)s is the main emission.
次に電極間に短形波５００ ＨｚでＩＯＶの電圧を印加
したところ両化合物共に発光するが、青色がまさって表
示素子は鮮やかな青色発光色へ瞬時に変化した。発光ス
ペクトルの電圧依存度を第３図に示すが、はぼＩＯＶで
一定発光色となることが判明した。電圧印加時は！４図
に示すように二色性発光色素であるジフェニルヘキサト
リエンがセル面と平行になることにより励起光を吸収し
、それに伴ない青色の強く発光を行うことによる。従り
て、この素子は赤−青のマルチカラー発光液晶ディスグ
レイとして作動する。Next, when a voltage of IOV was applied between the electrodes with a rectangular wave of 500 Hz, both compounds emitted light, but the blue color was predominant and the display element instantly changed to a bright blue light emitting color. The voltage dependence of the emission spectrum is shown in FIG. 3, and it was found that the emission color was constant at IOV. When voltage is applied! As shown in Figure 4, diphenylhexatriene, which is a dichroic luminescent dye, absorbs excitation light by becoming parallel to the cell surface, and accordingly emits strong blue light. Therefore, this device operates as a red-blue multi-color light-emitting liquid crystal display.
実施例２
４−シアノフェニルシクロヘキサン系等の液晶混合′物
（メルク社商品記号ＺＬＩ −１８４０）中に緑色の発
光色素ペリレン系色素（化合物２４）を０．３部、赤色
の発光色素クマリン系色素（化合物１９）０．５部を溶
解させた組成物をＳＩＯを斜め蒸着して平行配向処理し
た表示セル内に封入した。Example 2 0.3 parts of a green luminescent dye perylene dye (compound 24) was added to a liquid crystal mixture such as 4-cyanophenylcyclohexane (product code: ZLI-1840, Merck & Co., Ltd.), and a red luminescent dye coumarin dye. A composition in which 0.5 part of (Compound 19) was dissolved was sealed in a display cell in which SIO was obliquely deposited and subjected to parallel alignment treatment.
この状態でセル背面から４１０〜４４０の励起光を照射
すると表示素子は赤色の啄めて鮮やかな発光色を呈する
。これは第５図に示すように、等方的色素２４からの発
光も観測されるが、それに比べて二色性発光体である化
合物１９はセル面と平行であるので吸光ｔ１が大きく、
発光収率も高いため発光が非常に強いことによる。In this state, when excitation light of 410 to 440 is irradiated from the back of the cell, the display element emits bright red light. As shown in FIG. 5, light emission from the isotropic dye 24 is also observed, but in comparison, compound 19, which is a dichroic light emitter, has a large absorption t1 because it is parallel to the cell surface.
This is because the luminescence yield is high and the luminescence is very strong.
次に′を代極間に短形波３２ Ｈｚで５ｖの電圧を印加
したところ、表示素子は鮮やかな緑色発光色へ瞬時に変
化した。上圧印加時は第６図に示すように、二色性色素
である化合物１９がセル面と垂直になり励起光を吸収せ
ず、従りて赤色発光が見られなくなるが、等方的な化合
物２４は液晶分子の配向にかかわらず、励起光を吸収す
るので緑色発光を行う。従って、この素子は、琢−緑の
マルチカラー発光ディスプレイとして作動する。Next, when a voltage of 5 V with a rectangular wave of 32 Hz was applied between the electrodes, the display element instantly changed its luminous color to bright green. When upper pressure is applied, as shown in Figure 6, compound 19, which is a dichroic dye, becomes perpendicular to the cell surface and does not absorb excitation light, so no red light is emitted, but isotropic Compound 24 emits green light because it absorbs excitation light regardless of the orientation of the liquid crystal molecules. The device thus operates as a amber-green multicolor luminescent display.
実施例１，２で用いた色素の二色比を表１に示す。Table 1 shows the dichroic ratios of the dyes used in Examples 1 and 2.
表 １
化合物８ ＺＬＩ−２８０６１０Ｖ ７．８
７．５ （２色）化合物３３ ＺＬＩ−２８０６１０
Ｖ １．２ １．２（赤色）化合物１９ ＺＬ
Ｉ−１８０４５Ｖ ８，７ ８．８ （赤色）化
合物２４ ＺＬＩ−１８０４５Ｖ １．６ １
．５（緑色）以上は、透過型発光表示装置について説明
したものであるが、本発明は上記以外にも背面に反射基
板を用いて反射型表示装置としても応用可能であること
は明らかである。その際には励起光源は不要な場合もあ
る。Table 1 Compound 8 ZLI-280610V 7.8
7.5 (Two colors) Compound 33 ZLI-280610
V 1.2 1.2 (red) Compound 19 ZL
I-18045V 8,7 8.8 (Red) Compound 24 ZLI-18045V 1.6 1
．． 5 (Green) The above description is about a transmissive light emitting display device, but it is clear that the present invention can also be applied to a reflective display device other than the above by using a reflective substrate on the back surface. In that case, an excitation light source may not be necessary.
「発明の効果」
以上から明らかな如く、本発明によれば二色比の大きい
発光性色素と二色比の小さい発光性色素を組合せて用い
ることにより、マルチカラー表示用としてコントラスト
の高い優れた液晶組成物および液晶表示素子を提供する
ことが出来る。"Effects of the Invention" As is clear from the above, according to the present invention, by using a combination of a luminescent dye with a large dichroic ratio and a luminescent dye with a small dichroic ratio, an excellent product with high contrast can be obtained for multicolor display. A liquid crystal composition and a liquid crystal display element can be provided.
第１図は、本発明にかかる発光型表示装置の一実施例の
構成を示す模式図である。第２図、第４図、第５図およ
び第６図は、第１図て示す装置の表示作動原理を示す回
路模式図である。ｆ４３図は本発明にかかる液晶組成物
の一実施例につい七の発光スイクトル変化の電圧依存性
を示すグラフ図である。
１・・・表示電極、２・・・透明電極、３・・・シール
材料、４・・・液晶分子配向層、５・・・液晶組成混合
物、６・・・スイッチ、７・・・交流電源、８・・・液
晶分子、９・・・高二色比発光色素分子、１０・・・等
方性発光色素分子、１１・・・励起光、１２・・・等方
性発光色素分子からの発光、１３・・・高二色比発光色
素分子の発光。
、第５図
第６図
■２
第４図
■ の
御縁ぼ櫻FIG. 1 is a schematic diagram showing the configuration of an embodiment of a light-emitting display device according to the present invention. FIGS. 2, 4, 5, and 6 are schematic circuit diagrams showing the principle of display operation of the device shown in FIG. 1. Fig. f43 is a graph showing the voltage dependence of seven luminescence quiescent changes for one example of the liquid crystal composition according to the present invention. DESCRIPTION OF SYMBOLS 1... Display electrode, 2... Transparent electrode, 3... Seal material, 4... Liquid crystal molecule alignment layer, 5... Liquid crystal composition mixture, 6... Switch, 7... AC power supply , 8... Liquid crystal molecule, 9... High dichroic ratio luminescent dye molecule, 10... Isotropic luminescent dye molecule, 11... Excitation light, 12... Light emission from isotropic luminescent dye molecule , 13... Luminescence of high dichroic luminescent dye molecules. , Figure 5, Figure 6 ■2, Figure 4■, the matchmaking cherry tree
Claims (2)
直な方向の吸光度または発光強度の比で定義される二色
比が５以上の発光性化合物と２以下の発光性化合物を含
有せるネマチックまたはコレステリック液晶組成物。(1) Nematic containing a luminescent compound with a dichroic ratio of 5 or more and a luminescent compound of 2 or less, defined as the ratio of absorbance or luminescence intensity in the direction of the molecular axis to absorbance or luminescence intensity in the direction perpendicular to the molecular axis or cholesteric liquid crystal compositions.
直な方向の吸光度または発光強度の比で定義される二色
比が５以上の発光性化合物と２以下の発光性化合物を含
有せるネマチックまたはコレステリック液晶組成物を封
入せるマルチカラー液晶表示素子。(2) Nematic containing a luminescent compound with a dichroic ratio of 5 or more and a luminescent compound of 2 or less, defined as the ratio of absorbance or luminescence intensity in the direction of the molecular axis to absorbance or luminescence intensity in the direction perpendicular to the molecular axis Or a multicolor liquid crystal display element filled with a cholesteric liquid crystal composition.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6391886A JPS62220578A (en) | 1986-03-24 | 1986-03-24 | Liquid crystal composition and multi-color liquid crystal display element |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6391886A JPS62220578A (en) | 1986-03-24 | 1986-03-24 | Liquid crystal composition and multi-color liquid crystal display element |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62220578A true JPS62220578A (en) | 1987-09-28 |
Family
ID=13243199
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6391886A Pending JPS62220578A (en) | 1986-03-24 | 1986-03-24 | Liquid crystal composition and multi-color liquid crystal display element |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62220578A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03248121A (en) * | 1991-02-08 | 1991-11-06 | Hitachi Ltd | Liquid crystal display element |
| JPH03249621A (en) * | 1991-02-08 | 1991-11-07 | Hitachi Ltd | Liquid crystal display element |
| CN102199093A (en) * | 2011-04-11 | 2011-09-28 | 北京科技大学 | Perylene disc-shaped liquid-crystal compound and preparation method thereof |
| WO2021161860A1 (en) * | 2020-02-10 | 2021-08-19 | 三菱ケミカル株式会社 | Composition containing semiconductor nanoparticles, color filter, and image display device |
-
1986
- 1986-03-24 JP JP6391886A patent/JPS62220578A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03248121A (en) * | 1991-02-08 | 1991-11-06 | Hitachi Ltd | Liquid crystal display element |
| JPH03249621A (en) * | 1991-02-08 | 1991-11-07 | Hitachi Ltd | Liquid crystal display element |
| CN102199093A (en) * | 2011-04-11 | 2011-09-28 | 北京科技大学 | Perylene disc-shaped liquid-crystal compound and preparation method thereof |
| WO2021161860A1 (en) * | 2020-02-10 | 2021-08-19 | 三菱ケミカル株式会社 | Composition containing semiconductor nanoparticles, color filter, and image display device |
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