JPS62297382A - Organic electrochromic material - Google Patents
Organic electrochromic materialInfo
- Publication number
- JPS62297382A JPS62297382A JP14024386A JP14024386A JPS62297382A JP S62297382 A JPS62297382 A JP S62297382A JP 14024386 A JP14024386 A JP 14024386A JP 14024386 A JP14024386 A JP 14024386A JP S62297382 A JPS62297382 A JP S62297382A
- Authority
- JP
- Japan
- Prior art keywords
- group
- present
- groups
- electrochromic material
- compound
- 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.)
- Granted
Links
- 239000000463 material Substances 0.000 title claims abstract description 14
- -1 hydrazone compound Chemical class 0.000 claims abstract description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
- 125000002541 furyl group Chemical group 0.000 claims abstract description 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 abstract 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 abstract 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 14
- 239000007788 liquid Substances 0.000 description 6
- 238000004040 coloring Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 239000003115 supporting electrolyte Substances 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 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
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 101100136092 Drosophila melanogaster peng gene Proteins 0.000 description 1
- 239000005041 Mylar™ Substances 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
Abstract
Description
【発明の詳細な説明】
３、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酸化還元反応により可逆的に発
消色する改良されたを機エレクトロクロミンク材料に関
する。Detailed Description of the Invention 3. Detailed Description of the Invention <Industrial Field of Application> The present invention relates to an improved electrochromic material that reversibly develops and fades color through redox reaction upon application of voltage.
〈従来の技術〉
近年、生活環境のエレクトロニクス化が進むにつれ、人
間の視覚を対象とした表示素子への関心が急激に高まり
つつある。中でも非発光型素子として知られるエレクト
ロニクス・ツク素子は、■通常の周囲光下で印刷物同様
に目になじみ、発光ダイオードの如く外光によりみづら
くなることがなく、つまり換言すれば従来から使用され
ている液晶と比べて視野角の依存性がな（鮮やかな色彩
表示になること、■駆動電圧が０．５〜５■と低く、単
位電池からの直接駆、動が可能でＭＯＳ−ＩＣとの適合
性が良いこと、■素子構造が概して簡単で液晶表示の如
く電極間距離を精密に制御する必要がないこと、■大画
面化が容易であること、■動作温度範囲が広いこと、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。<Prior Art> In recent years, as the living environment has become increasingly electronic, interest in display elements for human vision has rapidly increased. Among them, electronic devices, which are known as non-emissive devices, fit the eye like printed matter under normal ambient light, and unlike light-emitting diodes, they do not become difficult to see due to external light. Compared to LCDs, there is less viewing angle dependence (brighter color display), drive voltage is as low as 0.5 to 5, direct drive from unit batteries is possible, and MOS-IC ■The element structure is generally simple and there is no need to precisely control the distance between electrodes like in a liquid crystal display, ■It is easy to make a large screen, ■It has a wide operating temperature range, etc. It is attracting attention because it has many excellent features.
従来から提案されている代表的なエレクトロクロミック
材料としては、低分子ビオロゲン誘導体（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
（ＷＯｓ）などの無機化合物がある。Typical electrochromic materials that have been proposed in the past include organic compounds such as low molecular weight viologen derivatives (4,4'-bipyridine derivatives) and inorganic compounds such as tungsten oxide (WOs).
これらのなかで低分子ビオロゲン誘導体などの有機化合
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 such as low-molecular-weight viologen derivatives can provide more vivid color display than inorganic compounds.
Moreover, it has the advantage that various colors can be selected by selecting the derivative.
しかしながら、低分子ビオロゲン誘導体溶液を用いたデ
ィスプレイでは繰返し表示寿命が短いこと、応答速度が
不十分であること、可視光領域に吸収を持つため非発色
状態においても地発色が生ずることなどのために実用化
のレベルに達していないのが現状である。However, displays using low-molecular-weight viologen derivative solutions have a short repeated display life, insufficient response speed, and because they absorb in the visible light region, background coloration occurs even in non-coloring states. At present, it has not reached the level of practical application.
〈発明が解決しようとする問題点〉
本発明は上記の問題に鑑みなされたものであり、耐久性
があり応答速度が早く、且つ地発色のない改良された有
機エレクトロクロミック材料を提供することを目的とす
る。<Problems to be Solved by the Invention> The present invention has been made in view of the above problems, and an object of the present invention is to provide an improved organic electrochromic material that is durable, has a fast response speed, and does not develop background color. purpose.
く問題点を解決するための手段〉
本発明は一般式
〔式中、Ｒ，はフェニル基又はカルバゾール基、フリル
基、ピリジル基、ベンゾイミダゾール基、ベンゾオキサ
ゾール基、ベンゾチアゾール基などの複素環基を示す。Means for Solving the Problems> The present invention is based on the general formula [wherein R is a phenyl group or a heterocyclic group such as a carbazole group, a furyl group, a pyridyl group, a benzimidazole group, a benzoxazole group, or a benzothiazole group] shows.
これらフェニル基および複素環基は、メチル基、エチル
基、プロピル基、ブチル基、アミル基などのアルキル基
、メトキシ基、エトキシ基、プロポキシ基、ブトキシ基
などのアルコキシ基、ジメチルアミノ基、ジエチルアミ
ノ基、ジプロピルアミノ基、ジブチルアミノ基、ジベン
ジルアミノ基、ジフェニルアミノ基、ジトリルアミノ基
、ジー置換アミノ基などのジー置換アミノ基、塩素原子
、臭素原子などのハロゲン原子、ヒドロキシ基、カルボ
キシ基などによって置換されてもよい。特に、Ｒ，はジ
ー置換アルキルアミノ基を４位に有するフェニル基が適
している。These phenyl groups and heterocyclic groups include alkyl groups such as methyl, ethyl, propyl, butyl and amyl groups, alkoxy groups such as methoxy, ethoxy, propoxy and butoxy groups, dimethylamino and diethylamino groups. , di-substituted amino groups such as dipropylamino group, dibutylamino group, dibenzylamino group, diphenylamino group, ditolylamino group, di-substituted amino group, halogen atoms such as chlorine atom, bromine atom, hydroxy group, carboxy group, etc. May be replaced. In particular, a phenyl group having a di-substituted alkylamino group at the 4-position is suitable for R.
Ｒ２は、水素原子、アリール基（例えば、〕工ニル基、
ナフチル基など）または置換子り−ル基（例えば、４−
ジメチルアミノフェニル基、４−ジエチルアミノフェニ
ル基、４−ジプロピルアミノフェニル基、４−メトキシ
フェニル基、４−エトキシフェニル基、２−メチルフェ
ニル基、２．４−ジメトキシフェニル基など）を示す。R2 is a hydrogen atom, an aryl group (for example, an engineering nyl group,
naphthyl group) or substituent lyl group (e.g. 4-
(dimethylaminophenyl group, 4-diethylaminophenyl group, 4-dipropylaminophenyl group, 4-methoxyphenyl group, 4-ethoxyphenyl group, 2-methylphenyl group, 2,4-dimethoxyphenyl group, etc.).
Ｒ３およびＲ４は、メチル基、エチル基、プロピル基、
ブチル基、アミル基などのアルキル基、フェニル基、ナ
フチル基などのアリール基、ベンジル基、フェネチル基
などのアラルキル基を示す。ｎは、０またはｌである。R3 and R4 are a methyl group, an ethyl group, a propyl group,
This refers to alkyl groups such as butyl and amyl groups, aryl groups such as phenyl and naphthyl groups, and aralkyl groups such as benzyl and phenethyl groups. n is 0 or l.
〕で示されるヒドラゾン化合物からなる有機エレクトロ
クロミック材料を提供するものである。The present invention provides an organic electrochromic material comprising a hydrazone compound represented by the following.
本発明で用いうるヒドラゾン化合物の代表例を下記に列
挙する。Representative examples of hydrazone compounds that can be used in the present invention are listed below.
化合物陽 ０８１ Ｃ、Ｈ。compound yang 081 C,H.
本発明の上記各化合物は、例えば溶媒および支持電解質
などを用いてエレクトロクロミック液に調製され表示素
子に適用される。Each of the above compounds of the present invention is prepared into an electrochromic liquid using, for example, a solvent and a supporting electrolyte, and then applied to a display element.
なお、本発明の有機エレクトロクロミック材料は上記に
例示したヒドラゾン化合物であるが、これらの化合物の
構造をペンダント基として含む高分子化合物およびこれ
らの構造を構造体中に含む高分子化合物についてもエレ
クトロクロミック材料としての機能を存することが期待
される。The organic electrochromic material of the present invention is the hydrazone compound exemplified above, but it is also applicable to polymer compounds containing the structures of these compounds as pendant groups and polymer compounds containing these structures in their structures. It is expected that it will function as a material.
以下、本発明の実施例について詳述する。Examples of the present invention will be described in detail below.
〈実施例〉
第１図は本発明による有機エレクトロクロミック材料が
適用される表示素子の構成を示すもので例えば透明また
は半透明な表示電極１を備えた透明基板２と、対向電極
（背面電極）３を備えた支持体４との間にマイラー、テ
フロンなどの絶縁スペーサ５を介して本発明によるエレ
クトロクロミック液６を封入し、シール７で密封して構
成される。表示電極は酸化インジウム、酸化スズ、酸化
インジウムスズなどの透明電極材料で形成され、対向電
極は上記透明電極材料と同じかあるいは白金、金、アル
ミニウムなどの金属で形成されている。また、支持体は
ガラス、プラスチックなどの材料からなるものである。<Example> Fig. 1 shows the structure of a display element to which the organic electrochromic material according to the present invention is applied. The electrochromic liquid 6 according to the present invention is sealed between the electrochromic liquid 6 and the support 4 provided with the electrochromic liquid 3 through an insulating spacer 5 such as Mylar or Teflon, and sealed with a seal 7. The display electrode is made of a transparent electrode material such as indium oxide, tin oxide, or indium tin oxide, and the counter electrode is made of the same material as the transparent electrode material or a metal such as platinum, gold, or aluminum. Further, the support is made of a material such as glass or plastic.
上記エレクトロクロミック液６として、先に例示したＩ
ｌｈ （１）の化合物ｌ ｍｍｏｌと、支持電解質とじ
ての臭化セチルトリメチルアンモニウム（ＣＴＡＢ）
０．１鵬ｏ１ とを１０１００Ｏ！のアセトニトリルに
溶解せしめた液を調製し、素子内に封入充満した。しか
るのち表示電極１および対向電極３の間に直流電工２〜
５ｖを印加したところ、表示電極ｌの上に赤色の発色が
みられた。印加電圧を除くことにより、もしくは１■程
度の逆極性の電圧をあたえることにより、この発色はす
みやかに消失した。As the electrochromic liquid 6, I
lmmol of compound lh(1) and cetyltrimethylammonium bromide (CTAB) as supporting electrolyte.
0.1 Peng o1 and 10100 O! A solution was prepared by dissolving this in acetonitrile, and the solution was sealed and filled into the device. Then, between the display electrode 1 and the counter electrode 3, a DC electrician 2~
When 5V was applied, a red color was observed on the display electrode 1. This coloring disappeared immediately by removing the applied voltage or by applying a voltage of about 1 square inch of opposite polarity.
本発明で示す有機エレクトロクロミック材料の応用に関
しては、実施例の如きいわゆる溶液型セルに限られるも
のではない。先にも述べたとおり本発明に示す化合物を
高分子化合物のペンダント基として高分子中に導入して
も、エレクトロクロミズムを示し、この手段においては
固体型セルへの応用も可能である。また本発明で示す化
合物に適当な大きさの化合物を結合せしめ、分子量を増
大させることにより、電極表面で発生した発色種の泳動
を制御することも可能である。The application of the organic electrochromic material shown in the present invention is not limited to so-called solution type cells as in the embodiments. As mentioned above, even when the compound shown in the present invention is introduced into a polymer as a pendant group of the polymer compound, electrochromism is exhibited, and this means can also be applied to solid-state cells. Furthermore, by binding a compound of an appropriate size to the compound shown in the present invention to increase its molecular weight, it is also possible to control the migration of colored species generated on the electrode surface.
〈発明の効果〉
本発明は上記の化合物から構成され、この化合物は発色
種と推測されるカチオン・ラジカルとそれに対応する中
性分子との間の可逆性が良好であるので、ラジカル状態
から他の化合物に変化する反応が少くなり、特定の色へ
の発色・消色のくり返し特性すなわち安定した耐久性が
得られ、又、従来知られている有機エレクトロクロミッ
ク材料例えばポルフィリン系化合物あるいはビオロゲン
系化合物が本来可視光領域に吸収を持ち、表示が色の変
化でなされるのに対し、本発明で示す化合物は、非発色
状態では可視領域には吸収がなく、電気化学的に発色種
を生じせしめた時にのみ発色するのでいわゆる地発色が
ないという秀れた特徴を有している。<Effects of the Invention> The present invention is composed of the above-mentioned compound, and this compound has good reversibility between the cation radical, which is assumed to be a coloring species, and the corresponding neutral molecule, so that it can be easily removed from the radical state. The reaction of changing into a compound is reduced, and the property of repeating coloring and decoloring to a specific color, that is, stable durability, is obtained. In contrast, the compound shown in the present invention does not absorb in the visible region in a non-coloring state and can electrochemically generate colored species. It has the excellent feature of not having so-called background coloration because it only develops color when it is exposed to sunlight.
第１図は本発明のエレクトロクロミック表示素子の一例
を示す概略断面図である。
１・・・表示電極、２・・・透明基板、３・・・対向電
極、４・・・支持体、５・・・スペーサ、６・・・エレ
クトロクロミック液、７・・・シール。FIG. 1 is a schematic cross-sectional view showing an example of the electrochromic display element of the present invention. DESCRIPTION OF SYMBOLS 1... Display electrode, 2... Transparent substrate, 3... Counter electrode, 4... Support, 5... Spacer, 6... Electrochromic liquid, 7... Seal.
Claims (1)
ル基、ピリジル基、ベンゾイミダゾール基、ベンゾオキ
サゾール基、ベンゾチアゾール基などの複素環基を示し
、Ｒ＿２は水素原子、アリール基または置換アリール基
を示し、Ｒ＿３およびＲ＿４はアルキル基、アリール基
又はアラルキル基を示す。 ｎは、０又は１である）で示されるヒドラゾン化合物か
らなる有機エレクトロクロミック材料。[Claims] General formula (wherein R_1 represents a phenyl group or a heterocyclic group such as a carbazole group, furyl group, pyridyl group, benzimidazole group, benzoxazole group, benzothiazole group, R_2 is a hydrogen atom, An organic electrochromic material consisting of a hydrazone compound, wherein R_3 and R_4 represent an alkyl group, an aryl group, or an aralkyl group; n is 0 or 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61140243A JP2548540B2 (en) | 1986-06-18 | 1986-06-18 | Organic electrochromic material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61140243A JP2548540B2 (en) | 1986-06-18 | 1986-06-18 | Organic electrochromic material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62297382A true JPS62297382A (en) | 1987-12-24 |
| JP2548540B2 JP2548540B2 (en) | 1996-10-30 |
Family
ID=15264241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61140243A Expired - Lifetime JP2548540B2 (en) | 1986-06-18 | 1986-06-18 | Organic electrochromic material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2548540B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1288275A2 (en) * | 2001-09-04 | 2003-03-05 | Exon Science Inc. | Electrochromic solution containing a hydrazone compound and device manufactured with same |
| WO2008007563A1 (en) | 2006-07-12 | 2008-01-17 | Konica Minolta Holdings, Inc. | Electrochromic display device |
-
1986
- 1986-06-18 JP JP61140243A patent/JP2548540B2/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1288275A2 (en) * | 2001-09-04 | 2003-03-05 | Exon Science Inc. | Electrochromic solution containing a hydrazone compound and device manufactured with same |
| US6567204B1 (en) * | 2001-09-04 | 2003-05-20 | Exon Science, Inc. | Electrochromic solution containing hydrazone compound and device manufactured with same |
| US6587251B2 (en) * | 2001-09-04 | 2003-07-01 | Exon Science, Inc. | Electrochromic solution containing hydrazone compound and device manufactured with same |
| EP1288275A3 (en) * | 2001-09-04 | 2004-06-23 | Exon Science Inc. | Electrochromic solution containing a hydrazone compound and device manufactured with same |
| WO2008007563A1 (en) | 2006-07-12 | 2008-01-17 | Konica Minolta Holdings, Inc. | Electrochromic display device |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2548540B2 (en) | 1996-10-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |