JPH0134365B2 - - Google Patents
Info
- Publication number
- JPH0134365B2 JPH0134365B2 JP56137488A JP13748881A JPH0134365B2 JP H0134365 B2 JPH0134365 B2 JP H0134365B2 JP 56137488 A JP56137488 A JP 56137488A JP 13748881 A JP13748881 A JP 13748881A JP H0134365 B2 JPH0134365 B2 JP H0134365B2
- Authority
- JP
- Japan
- Prior art keywords
- display
- voltage
- substance
- ecd
- group
- 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
Links
- 239000000126 substance Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 238000004040 coloring Methods 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 238000006722 reduction reaction Methods 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 2
- 238000004042 decolorization Methods 0.000 claims 1
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims 1
- 150000002990 phenothiazines Chemical class 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229950000688 phenothiazine Drugs 0.000 description 3
- 239000003115 supporting electrolyte Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 235000019646 color tone Nutrition 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- RVBAUHGQSLEOSR-UHFFFAOYSA-N phenothiazin-10-yl(phenyl)methanone Chemical compound C12=CC=CC=C2SC2=CC=CC=C2N1C(=O)C1=CC=CC=C1 RVBAUHGQSLEOSR-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 2
- 229910052939 potassium sulfate Inorganic materials 0.000 description 2
- 235000011151 potassium sulphates Nutrition 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229940066767 systemic antihistamines phenothiazine derivative Drugs 0.000 description 2
- WGHUNMFFLAMBJD-UHFFFAOYSA-M tetraethylazanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CC[N+](CC)(CC)CC WGHUNMFFLAMBJD-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- LWHWMTSEFMWPIX-UHFFFAOYSA-N 1,2-dinitro-10h-phenothiazine Chemical compound C1=CC=C2NC3=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C3SC2=C1 LWHWMTSEFMWPIX-UHFFFAOYSA-N 0.000 description 1
- CLLWSJFJLBXJBT-UHFFFAOYSA-N 10h-phenothiazin-1-yl(phenyl)methanone Chemical compound C=1C=CC=2SC3=CC=CC=C3NC=2C=1C(=O)C1=CC=CC=C1 CLLWSJFJLBXJBT-UHFFFAOYSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- RBTBFTRPCNLSDE-UHFFFAOYSA-N 3,7-bis(dimethylamino)phenothiazin-5-ium Chemical compound C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 RBTBFTRPCNLSDE-UHFFFAOYSA-N 0.000 description 1
- MWVTWFVJZLCBMC-UHFFFAOYSA-N 4,4'-bipyridine Chemical class C1=NC=CC(C=2C=CN=CC=2)=C1 MWVTWFVJZLCBMC-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- ZKURGBYDCVNWKH-UHFFFAOYSA-N [3,7-bis(dimethylamino)phenothiazin-10-yl]-phenylmethanone Chemical compound C12=CC=C(N(C)C)C=C2SC2=CC(N(C)C)=CC=C2N1C(=O)C1=CC=CC=C1 ZKURGBYDCVNWKH-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- AXZAYXJCENRGIM-UHFFFAOYSA-J dipotassium;tetrabromoplatinum(2-) Chemical compound [K+].[K+].[Br-].[Br-].[Br-].[Br-].[Pt+2] AXZAYXJCENRGIM-UHFFFAOYSA-J 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 1
- 229910001486 lithium perchlorate Inorganic materials 0.000 description 1
- 230000006386 memory function Effects 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005596 polymer binder Polymers 0.000 description 1
- 239000002491 polymer binding agent Substances 0.000 description 1
- 239000005518 polymer electrolyte Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 229910001487 potassium perchlorate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- ZNOKGRXACCSDPY-UHFFFAOYSA-N tungsten trioxide Chemical compound O=[W](=O)=O ZNOKGRXACCSDPY-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Landscapes
- Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
Description
【発明の詳細な説明】
この発明は、電圧印加による酸化還元反応によ
り可逆的に発消色する新規な有機エレクトロクロ
ミツク物質を用いた表示素子に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a display element using a novel organic electrochromic substance that reversibly develops and fades color through redox reactions caused by voltage application.
エレクトロクロミツク表示素子（以下ECD素
子と略記する）では、電圧を印加することにより
透明表示電極でEC物質の酸化または還元反応が
おこり着色パターンが形成され、逆極性電圧を印
加することにより逆反応で着色パターンが消色す
るという機構を利用している。 In electrochromic display elements (hereinafter abbreviated as ECD elements), applying a voltage causes an oxidation or reduction reaction of the EC substance at the transparent display electrode, forming a colored pattern, and applying a voltage of opposite polarity causes a reverse reaction. It uses a mechanism in which the colored pattern disappears.
このような機構で発消色するECD素子は、受
光型の表示素子として従来から使用されている液
晶と比べて視野角の依存性がなく、鮮やかな色彩
表示により見やすいことや、メモリー機能を持つ
こと、動作温度範囲が広いこと、大画面化が容易
であることなどの多くの優れた特長を有している
ために注目されている。 Compared to liquid crystals, which have been traditionally used as light-receiving display elements, ECD elements that produce and erase colors using this mechanism are less dependent on viewing angle, display brighter colors, are easier to see, and have a memory function. It is attracting attention because it has many excellent features, such as a wide operating temperature range, and the ability to easily increase the screen size.
従来から提案されている代表的なEC物質とし
ては、ビオロゲン誘導体（４、4′−ビピリジン誘
導体）などの有機化合物や酸化タングステン
（WO3）、酸化モリブデン（M0O3）などの無機化
合物がある。 Typical EC substances that have been proposed include organic compounds such as viologen derivatives (4,4'-bipyridine derivatives) and inorganic compounds such as tungsten oxide (WO 3 ) and molybdenum oxide (M 0 O 3 ). be.
これらのなかで有機化合物は無機化合物と比較
して鮮やかな色彩表示が得られ、しかも誘導体の
選択により種々の色彩を選択できるという特長が
ある。 Among these, organic compounds have the advantage that they provide more vivid color display than inorganic compounds, and that various colors can be selected by selecting the derivative.
しかしながら、現段階では有機化合物を使つた
ECD素子では繰返し表示寿命が短いことやメモ
リ寿命が不十分であることなどのために実用化の
レベルには達していない。また発色する色彩とし
ても比較的限られた種類であり、任意な色に発色
でき、しかも表示の繰返し安定性のよい新しい
EC物質が要求されている。 However, at present, it is difficult to use organic compounds.
ECD elements have not yet reached the level of practical use due to their short repeated display life and insufficient memory life. In addition, the types of colors that can be produced are relatively limited, and a new type of color that can be produced in any color and has good repeatable display stability.
EC substances are required.
この発明は、従来、EC物質としては知られて
いない有機化合物が、上記要件を満すEC物質と
しての性質を備えていることを見出し、このEC
物質に適した構成としたECD素子を提案するも
のである。 The present invention has been made based on the discovery that an organic compound that has not been previously known as an EC substance has the properties of an EC substance that satisfies the above requirements.
This paper proposes an ECD element with a configuration suitable for the material.
この発明によるEC物質は、下記一般式で表わ
されるフエノチアジン誘導体である。 The EC substance according to the present invention is a phenothiazine derivative represented by the following general formula.
ここで、式中ＲはＨ、Cl、By、Ｉ、Ｆ、炭素
数１乃至６のアルキル基、アルコキシ基、フエノ
キシ基、NO2、CN、NH2、Ｎ（CH3）2、COOH、
COOCH3、SO2NH2、SO3Na、であり、R′はH1
アシル基またはアルキル基を示す。 Here, in the formula, R is H, Cl, By, I, F, an alkyl group having 1 to 6 carbon atoms, an alkoxy group, a phenoxy group, NO 2 , CN, NH 2 , N(CH 3 ) 2 , COOH,
COOCH 3 , SO 2 NH 2 , SO 3 Na, and R′ is H 1
Indicates an acyl group or an alkyl group.
これらのフエノチアジン誘導体は、フエノチア
ジンを出発物質として通常の置換反応によりＲ基
の導入、またはＮ置換反応によりR′基の導入に
より合成される。 These phenothiazine derivatives are synthesized from phenothiazine as a starting material by introducing an R group through a conventional substitution reaction or by introducing an R' group through an N substitution reaction.
また、メチレンブルーの合成例に見られる下記
反応経路により合成することも可能である。 It is also possible to synthesize by the following reaction route seen in the synthesis example of methylene blue.
これらのフエノチアジン誘導体を用いてECD
素子を構成するには、水またはDMFなどの有機
溶剤、あるいは水と有機溶剤の混合溶剤に１×
10-5〜５モル１の濃度で溶解または分解し、更
に導電性を高めるために支持電解質を混入する。
支持電解質の例としては、塩化リチウム、塩化カ
リウム、塩化ナトリウム、臭化カリウム、硫酸カ
リウム、硫酸第１鉄、過塩素酸カリウム、過塩素
酸リチウム、過塩素酸テトラエチルアンモニウ
ム、ホウフツ化カリウム、リン酸カリウム、酢酸
カリウム等が目的に応じて0.01〜５モル／の範
囲で用いられる。 ECD using these phenothiazine derivatives
To construct the device, add 1x to water or an organic solvent such as DMF, or a mixed solvent of water and organic solvent.
It is dissolved or decomposed at a concentration of 10 -5 to 5 mol 1, and a supporting electrolyte is mixed in to further increase the conductivity.
Examples of supporting electrolytes include lithium chloride, potassium chloride, sodium chloride, potassium bromide, potassium sulfate, ferrous sulfate, potassium perchlorate, lithium perchlorate, tetraethylammonium perchlorate, potassium borofluoride, phosphoric acid. Potassium, potassium acetate, etc. are used in an amount of 0.01 to 5 mol/according to the purpose.
さらに、表示のコントラストを向上するために
白色無機顔料または高分子エマルジヨンを分散す
ることも有効であり、また白色無機顔料を溶液に
対して同量以上混合し全体をペースト状として用
いることも可能である。 Furthermore, it is also effective to disperse white inorganic pigments or polymer emulsions to improve display contrast, and it is also possible to mix at least the same amount of white inorganic pigments into the solution and use the entire solution as a paste. be.
このように調製したEC物質を第１図に示すよ
うなECD素子中に封入し、透明表示電極２を正
として対向電極３との間に直流電圧を印加すると
表示電極２をとおして鮮やかな色表示が得られ
る。 When the EC substance prepared in this manner is encapsulated in an ECD element as shown in Fig. 1, and a DC voltage is applied between the transparent display electrode 2 and the counter electrode 3 with the transparent display electrode 2 as positive, a bright color is produced through the display electrode 2. Display is obtained.
また、この発明に係るフエノチアジン誘導体を
用いた他のECD素子の構成として、第２図に示
すものがある。即ちフエノチアジン誘導体と高分
子バインダー樹脂と混合し、表示電極２の面上に
コーテイングして膜状のEC材料層６を形成する。
ここで用いる高分子バインダー樹脂としては、好
ましくは導電性を有する高分子電解質が適してい
る。この場合は、ECD素子内には前述の支持電
解質および無機電解質などからなる溶液７を充填
する。 Further, there is a configuration of another ECD element using the phenothiazine derivative according to the present invention as shown in FIG. That is, a phenothiazine derivative and a polymeric binder resin are mixed and coated on the surface of the display electrode 2 to form a film-like EC material layer 6.
As the polymer binder resin used here, preferably a conductive polymer electrolyte is suitable. In this case, the ECD element is filled with the solution 7 made of the above-mentioned supporting electrolyte, inorganic electrolyte, and the like.
このように構成したECD素子により表示され
る色調は用いるフエノチアジン誘導体により異な
り、例えばＮ−ベンゾイルフエノチアジン（一般
式中Ｒ＝Ｈ、R′＝C6H6CO−）では最初無色であ
るが、表示電極２を正とする電圧印加により青色
から緑色になり、表示電極２を負とする電圧印加
により無色の状態を経て赤紫色になる安定した繰
返し表示特性を有する。 The color tone displayed by the ECD element configured in this way varies depending on the phenothiazine derivative used. For example, N-benzoylphenothiazine (in the general formula, R = H, R' = C 6 H 6 CO-) is initially colorless. However, the color changes from blue to green when a positive voltage is applied to the display electrode 2, and changes from a colorless state to reddish-purple when a negative voltage is applied to the display electrode 2, and has a stable repeating display characteristic.
更に一般式中の置換基ＲとR′を選択すること
により他の色調の表示を得ることが可能である。 Furthermore, by selecting substituents R and R' in the general formula, it is possible to obtain display of other color tones.
以下、この発明で適用する新らしく見出した
EC物質を用いて構成したECD素子の例をあげて
具体的に説明するが、この発明はこれらのEC物
質、ECD素子の構成例に限定されるものではな
い。 Below, we will explain the new findings that can be applied to this invention.
Although an example of an ECD element constructed using an EC substance will be specifically explained, the present invention is not limited to these EC substances and the configuration examples of the ECD element.
実施例 １
フエノチアジンから合成した、Ｎ−ベンゾイル
フエノチアジン１ｇ、過塩素酸テトラエチルアン
モニウム0.5、酸化チタン2.5ｇ、酸化亜鉛５ｇを
ジメチルホルムアミド５mlに加えて混合したもの
をECD素子内に充填し第１図に示す構成のECD
素子を作成した。Example 1 A mixture of 1 g of N-benzoylphenothiazine synthesized from phenothiazine, 0.5 g of tetraethylammonium perchlorate, 2.5 g of titanium oxide, and 5 g of zinc oxide was added to 5 ml of dimethylformamide and filled into an ECD element. ECD with the configuration shown in Figure 1
The element was created.
透明表示電極を正として除々に電圧を印加して
いくと酸化反応を起していることを示す電流が観
測され、0.7Vで青色の、0.9Vで緑色のコントラ
ストのよい表示が得られた。つぎに逆極性の電圧
を加えるとすみやかに消色し、この発色−消色の
繰返しは安定して行うことができた。 When voltage was gradually applied with the transparent display electrode set as positive, a current indicating that an oxidation reaction was occurring was observed, and a blue display with good contrast was obtained at 0.7V and a green display at 0.9V. Next, when a voltage of opposite polarity was applied, the color was quickly decolored, and this coloring and decoloring process could be repeated stably.
また表示電極を負として電圧印加すると−
1.7Vで赤色の表示が得られ、−1.8Vと＋0.8Vの間
で繰返し電圧を印加すると赤色←→青色の繰返し表
示を行うことができた。 Also, when voltage is applied with the display electrode negative, -
A red display was obtained at 1.7V, and by repeatedly applying a voltage between -1.8V and +0.8V, it was possible to repeatedly display red←→blue.
実施例 ２
ベンゾイルロイコメチレンブルー（市販品）１
ｇを用いる以外は実施例１と同様にしてECD素
子を作成した。透明表示電極を正として除々に電
圧を印加していくと＋0.7Vで緑色のコントラス
トのよい表示が得られた。逆方向の電圧を加える
とすみやかに白色に戻り、この発明−消色の繰返
しは安定して行うことができた。Example 2 Benzoylleucomethylene blue (commercial product) 1
An ECD element was produced in the same manner as in Example 1 except that g was used. When voltage was gradually applied with the transparent display electrode set as positive, a green display with good contrast was obtained at +0.7V. When a voltage in the opposite direction was applied, the color quickly returned to white, and the decoloring process according to the present invention could be performed stably.
実施例 ８
発消色材料としてフエノチアジンをニトロ化し
て得られるジニトロフエノチアジンを用いること
と、酸化亜鉛のかわりに合成ゼオライト粉末を用
いる以外は実施例１と同様にしてECD素子を作
成した。Example 8 An ECD element was prepared in the same manner as in Example 1, except that dinitrophenothiazine obtained by nitration of phenothiazine was used as the coloring/discoloring material, and synthetic zeolite powder was used instead of zinc oxide.
これは最初赤色であり、表示電極を負として電
圧を印加すると−0.7Vで緑色になり、逆電圧を
印加すると赤色に戻り、緑←→赤色の繰返し表示を
安定に行うことができた。 This was red at first, and when a voltage was applied with the display electrode negative, it turned green at -0.7V, and when a reverse voltage was applied, it returned to red, making it possible to stably display green←→red repeatedly.
実施例 ４
アンモニウムポリアクリレートの30％メタノー
ル溶液５mlにベンゾイルフエノチアジン１ｇを加
えて、透明表示電極にコーテイングし、厚さ2μ
ｍの薄膜を作成した。これを用いてECD素子を
組み立て、この素子の中に硫酸カリウムの0.3モ
ル／水溶液を封入し、第２図に示す構成の
ECD素子を作成した。Example 4 1 g of benzoylphenothiazine was added to 5 ml of a 30% methanol solution of ammonium polyacrylate and coated on a transparent display electrode to a thickness of 2 μm.
A thin film of m was prepared. Using this, an ECD element was assembled, and a 0.3 mol/aqueous solution of potassium sulfate was sealed in the element, and the configuration shown in Figure 2 was prepared.
An ECD element was created.
表示電極側を正として電圧を印加すると、＋
1.0Vで青色の、＋1.2Vで緑色のコントラストのよ
い表示が得られた。逆方向の電圧を加えるとすみ
やかに消色し、この発色−消色の繰返しは安定に
行われた。 When voltage is applied with the display electrode side as positive, +
A blue display with good contrast was obtained at 1.0V, and a green display was obtained at +1.2V. When a voltage in the opposite direction was applied, the color quickly disappeared, and the repetition of coloring and decoloring was performed stably.
また表示電極を負として電圧を印加すると−
1.5Vで赤色の表示が得られ、−1.6Vと＋1.1Vの間
で繰返し電圧を印加すると赤色←→青色の繰返し表
示を行うことができた。 Also, when voltage is applied with the display electrode negative, -
A red display was obtained at 1.5V, and by repeatedly applying a voltage between -1.6V and +1.1V, it was possible to repeatedly display red←→blue.
この発明は直流電圧を印加したとき可逆的に生
じる酸化・還元反応に伴い当該物質の発色・消色
を生じるエレクトロクロミツク物質を用いた表示
素子において、上記エレクトロクロミツク物質と
して下記の一般式
〔但し、式中ＲはＨ、Cl、By、Ｉ、Ｆ、C1から
C6のアルキル基、アルコキシ基、フエノキシ基、
NO2、CN、NH2、Ｎ（CH3）2、COOH、
COOCH3、SO2NH2、またはSO3Naであり、
R′はＨ、アシル基またはアルキル基である。〕で
示されるフエノチアジン誘導体をエレクトロクロ
ミツク物質として用いることを特徴とするもので
各種の色表示が可能で、かつ寿命化が図れる効果
がある。 This invention relates to a display element using an electrochromic substance that develops or decolors the substance due to an oxidation/reduction reaction that occurs reversibly when a DC voltage is applied. [However, in the formula, R is from H, Cl, By, I, F, C 1
C6 alkyl group, alkoxy group, phenoxy group,
NO2 , CN, NH2 , N( CH3 ) 2 , COOH,
COOCH 3 , SO 2 NH 2 , or SO 3 Na;
R' is H, an acyl group or an alkyl group. It is characterized by using the phenothiazine derivative shown in ] as an electrochromic substance, and is capable of displaying various colors and has the effect of increasing the service life.
第１図はこの発明に係るEC物質を用いたECD
素子一実施例の断面図、第２図はこの発明の他の
実施例の断面図である。
図において、１はガラス基板、２は透明表示電
極、３は対向電極、４はエレクトロクロミツク物
質を含む溶液、５はスペーサ、６は膜状のEC材
料層、７は電解質溶液である。なお図中同一符号
はそれぞれ同一または相当部分を示す。
Figure 1 shows ECD using the EC substance according to this invention.
FIG. 2 is a cross-sectional view of one embodiment of the device, and FIG. 2 is a cross-sectional view of another embodiment of the invention. In the figure, 1 is a glass substrate, 2 is a transparent display electrode, 3 is a counter electrode, 4 is a solution containing an electrochromic substance, 5 is a spacer, 6 is a film-like EC material layer, and 7 is an electrolyte solution. Note that the same reference numerals in the figures indicate the same or corresponding parts.
Claims (1)
化・還元反応に伴い当該物質の発色・消色を生じ
るエレクトロクロミツク物質を用いた表示素子に
おいて、上記エレクトロクロミツク物質として下
記の一般式で示されるフエノチアジン誘導体を用
いることを特徴とするエレクトロクロミツク表示
素子。 〔但し、式中ＲはＨ、Cl、By、Ｉ、Ｆ、C1から
C6のアルキル基、アルコキシ基、フエノキシ基、
NO2、CN、NH2、Ｎ（CH3）2、COOH、
COOCH3、SO2NH2、またはSO3Naであり、
R′はＨ、アシル基またはアルキル基である。〕[Scope of Claims] 1. In a display element using an electrochromic substance that causes coloring or decolorization of the substance due to oxidation/reduction reactions that occur reversibly when a DC voltage is applied, the electrochromic substance is as follows: An electrochromic display element characterized by using a phenothiazine derivative represented by the general formula. [However, in the formula, R is from H, Cl, By, I, F, C 1
C6 alkyl group, alkoxy group, phenoxy group,
NO2 , CN, NH2 , N( CH3 ) 2 , COOH,
COOCH 3 , SO 2 NH 2 , or SO 3 Na;
R' is H, an acyl group or an alkyl group. ]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56137488A JPS5838782A (en) | 1981-09-01 | 1981-09-01 | Electrochromic display element |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56137488A JPS5838782A (en) | 1981-09-01 | 1981-09-01 | Electrochromic display element |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5838782A JPS5838782A (en) | 1983-03-07 |
| JPH0134365B2 true JPH0134365B2 (en) | 1989-07-19 |
Family
ID=15199809
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56137488A Granted JPS5838782A (en) | 1981-09-01 | 1981-09-01 | Electrochromic display element |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5838782A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201209496A (en) * | 2010-08-20 | 2012-03-01 | J Touch Corp | Electrochromic module combined with organic and inorganic materials and display device combined with the module |
-
1981
- 1981-09-01 JP JP56137488A patent/JPS5838782A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5838782A (en) | 1983-03-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2100939A1 (en) | Electrochromic compound and electrochromic display device using the same | |
| JPS608069B2 (en) | electrochromic display device | |
| JPH0134365B2 (en) | ||
| JPS59217787A (en) | Electrochromic material | |
| JPS59217791A (en) | Electrochromic material | |
| JPS6057320A (en) | Electrochromic display element | |
| JP2006235366A (en) | Gel electrolyte and electrochromic element using the same | |
| JPS6357478B2 (en) | ||
| JPS5838781A (en) | Electrochromic display element | |
| JPS61185730A (en) | Composite film type electrochromic material | |
| JPS61147235A (en) | Electrochromic display element | |
| JPS62115129A (en) | Electrochromic display element | |
| JPH01233283A (en) | Electrochromic display element | |
| JPH0340073B2 (en) | ||
| JPH0730314B2 (en) | Electrochromic display material | |
| JPS59217789A (en) | Electrochromic material | |
| JP2721766B2 (en) | Electrochromic material | |
| JPH0145893B2 (en) | ||
| JPS61223725A (en) | Electrochromic display element | |
| JPS59193981A (en) | Electrochromic material and display element using it | |
| JPS62297383A (en) | Organic electrochromic material | |
| JPH0361170B2 (en) | ||
| JPH0115551B2 (en) | ||
| KR810000053B1 (en) | Electrochromic composition | |
| JPH0726091B2 (en) | Electrochromic display device |