JPH0772269B2 - Electrochromic dimmer medium - Google Patents

Electrochromic dimmer medium

Info

Publication number
JPH0772269B2
JPH0772269B2 JP20036686A JP20036686A JPH0772269B2 JP H0772269 B2 JPH0772269 B2 JP H0772269B2 JP 20036686 A JP20036686 A JP 20036686A JP 20036686 A JP20036686 A JP 20036686A JP H0772269 B2 JPH0772269 B2 JP H0772269B2
Authority
JP
Japan
Prior art keywords
dimmer
medium
general formula
formula
transparent
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 - Fee Related
Application number
JP20036686A
Other languages
Japanese (ja)
Other versions
JPS6356590A (en
Inventor
治 河端
晴繁 中田
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Neos Co Ltd
Original Assignee
Neos Co Ltd
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 Neos Co Ltd filed Critical Neos Co Ltd
Priority to JP20036686A priority Critical patent/JPH0772269B2/en
Publication of JPS6356590A publication Critical patent/JPS6356590A/en
Publication of JPH0772269B2 publication Critical patent/JPH0772269B2/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Landscapes

  • Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)

Description

【発明の詳細な説明】 産業上の利用分野 本発明は新規なエレクトロクロミック調光体(以下、EC
調光体という)用媒体に関する。
The present invention relates to a novel electrochromic dimmer (hereinafter referred to as EC
A medium for light control).

従来の技術 EC調光体は従来のブラインドやカーテンに代わる調光体
として近年注目されている。EC調光体は透明電極上にEC
物質層を形成させた透明基板と、対向電極を形成させた
透明基板とを電解質を介在させて成る積層体である。
2. Description of the Related Art EC dimmers have been drawing attention in recent years as dimmers that replace conventional blinds and curtains. EC dimmer is EC on transparent electrode
It is a laminated body in which a transparent substrate on which a material layer is formed and a transparent substrate on which a counter electrode is formed are interposed with an electrolyte.

EC調光体は太陽光等の外光の入射量を電気光学的作用に
よって任意に制御し得るため建造物、車両、航空機等の
窓ガラス用調光体としての用途が期待されている。
EC dimmers are expected to be used as window dimmers for buildings, vehicles, aircrafts, etc., because the incident amount of outside light such as sunlight can be controlled arbitrarily by an electro-optical effect.

EC調光体用媒体には、電解質(例えば、過塩素酸リチウ
ム、塩化リチウム、ホウフッ化リチウム、過塩素酸ナト
リウム等)および各種の機能向上用添加剤(例えば、応
答性を改良するために添加された各種キレート化剤、消
色性を改良するために添加される含ヨウ素化合物、着色
時の応答性を改良するために添加されるトリクロル酢酸
やベンゼンスルホン酸等)を透明に溶解させる特性が不
可欠である。
In the medium for EC dimmer, an electrolyte (eg, lithium perchlorate, lithium chloride, lithium borofluoride, sodium perchlorate, etc.) and various function-improving additives (eg, added to improve responsiveness) Various chelating agents, iodine-containing compounds added to improve the decoloring property, trichloroacetic acid, benzenesulfonic acid, etc. added to improve the response at the time of coloring are transparently dissolved. It is essential.

しかしながら、従来からEC調光体用媒体として提案され
ている媒体、即ちポリビニルアルコール、ポリアクリル
アミド、エチレングリコール、ポリスチレン、ブチルア
ルコール等は、これらの要件を十分に満たしていない。
However, media conventionally proposed as EC dimmer media, such as polyvinyl alcohol, polyacrylamide, ethylene glycol, polystyrene, butyl alcohol, etc., do not fully meet these requirements.

発明が解決しょうとする問題点 本発明は、化学的に安定であって長期間の耐候性を有す
るだけでなく、電解質や各種の機能向上用添加剤を透明
に溶解させる特性を有する新規なEC調光体用媒体を提供
するためになされたものでる。
DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention The present invention is a novel EC having not only chemical stability and long-term weather resistance, but also the property of transparently dissolving an electrolyte and various function-enhancing additives. It was made to provide a medium for a dimmer.

問題点を解決するための手段 即ち本発明は、一般式[I]: (式中、R1は水素原子またはメチル基を示し、R2は炭素
原子数1〜4の側鎖を有していてもよいアルキル基を示
し、Xは炭素原子または硫黄原子を示す) で表される化合物または一般式[II]: [式中、Xは前記と同意義であり、Yは一般式[II
I]: −O−R2 [III] (式中、R2は前記と同意義である) で表される基または一般式[IV]: (式中、R3およびR4はそれぞれ独立して炭素原子数1〜
4の飽和または不飽和の側鎖を有してもよいアルキル
基、両者合して酸素原子を有することもある5員環もし
くは6員環を示す)で示される基を示す] で表わされる化合物を含有するエレクトロクロミック調
光体用媒体に関する。
Means for Solving the Problems That is, the present invention has the general formula [I]: (In the formula, R 1 represents a hydrogen atom or a methyl group, R 2 represents an alkyl group which may have a side chain having 1 to 4 carbon atoms, and X represents a carbon atom or a sulfur atom.) Compound represented or general formula [II]: [In the formula, X has the same meaning as described above, and Y represents the general formula [II
I]: —O—R 2 [III] (wherein R 2 has the same meaning as described above) or a general formula [IV]: (In the formula, R 3 and R 4 are each independently a carbon atom number of 1 to 1.
4 represents an alkyl group which may have a saturated or unsaturated side chain, and which represents a 5-membered ring or a 6-membered ring which may both have an oxygen atom) And a medium for electrochromic dimmer containing

上記の一般式[I]または[II]において、R1は水素原
子またはメチル基を示し、R2は炭素原子数1〜4の側鎖
を有していてもよいアルキル基、例えばメチル基、エチ
ル基、イソプロピル基またはイソブチル基を示し、Xは
炭素原子または硫黄原子を示し、Yは一般式[III]ま
たは[IV]で示される基を示す。
In the above general formula [I] or [II], R 1 represents a hydrogen atom or a methyl group, and R 2 is an alkyl group which may have a side chain having 1 to 4 carbon atoms, for example, a methyl group, It represents an ethyl group, an isopropyl group or an isobutyl group, X represents a carbon atom or a sulfur atom, and Y represents a group represented by the general formula [III] or [IV].

一般式[III]において、R2は前記と同意義であって、
炭素原子数1〜4の側鎖を有していてもよいアルキル基
を示す。
In the general formula [III], R 2 has the same meaning as defined above,
The alkyl group which may have a side chain having 1 to 4 carbon atoms is shown.

一般式[IV]において、R3およびR4は各々独立して炭素
原子数1〜4の飽和もしくは不飽和の側鎖を有していて
もよいアルキル基、例えば、メチル基、エチル基、イソ
プロピル基またはイソブチル基等を示し、あるいは両者
合して酸素原子を有することもある5員環もしくは6員
環を示す。
In the general formula [IV], R 3 and R 4 are each independently an alkyl group having 1 to 4 carbon atoms and optionally having a saturated or unsaturated side chain, for example, methyl group, ethyl group, isopropyl group. Represents a group or an isobutyl group, or represents a 5-membered ring or a 6-membered ring which may have an oxygen atom in combination with each other.

このような一般式[I]〜[IV]で表わされる化合物の
具体例を以下の表−1〜表−3に示す。
Specific examples of the compounds represented by the general formulas [I] to [IV] are shown in Tables 1 to 3 below.

一般式[I]〜[IV]で表わされる化合物は一般に低い
凝固点を有するため、窓ガラス、フロントガラス等とし
て屋外、特に寒冷地においてもしくは冬期に使用しても
凝結することがない。
Since the compounds represented by the general formulas [I] to [IV] generally have a low freezing point, they do not condense even when used outdoors such as window glasses and windshields, especially in cold regions or in the winter.

なお、凝固点が比較的高い化合物の場合には、凝固点の
低い他の溶剤、例えばブタノール、イソプロパノール、
プロピレンカーボネート等を適宜配合して使用すること
ができる。
Incidentally, in the case of a compound having a relatively high freezing point, another solvent having a low freezing point, for example, butanol, isopropanol,
Propylene carbonate and the like can be appropriately mixed and used.

さらに、一般式[I]〜[IV]で表わされる化合物は一
般に誘電率が高いので、EC調光体用媒体として使用した
場合の応答性は極めて高い。
Furthermore, since the compounds represented by the general formulas [I] to [IV] generally have a high dielectric constant, the response when used as a medium for an EC dimmer is extremely high.

さらにまた、一般式[I]〜[IV]で表わされる化合物
は、EC調光体用の前記の電解質や各種添加剤を実用上十
分な濃度まで透明に溶解させることができる。
Furthermore, the compounds represented by the general formulas [I] to [IV] can transparently dissolve the above-mentioned electrolyte for EC dimmer and various additives to a practically sufficient concentration.

本発明によるEC調光体用媒体は、例えば第1図の模式的
断面図に示すような構成で使用してもよい。即ち、2枚
の透明基板(1)の一方の内面に透明電極気(2)を設
け、該透明電極の上にEC層(3)を形成させ、他方の透
明基板の内面に対向電極(4)を形成させ、この2枚の
透明基板を相対置させて周縁部をシール材(6)で封止
し、内部に本発明によるEC調光体用媒体(5)を封入す
る。
The medium for an EC dimmer according to the present invention may be used, for example, in the configuration shown in the schematic sectional view of FIG. That is, the transparent electrode layer (2) is provided on one inner surface of the two transparent substrates (1), the EC layer (3) is formed on the transparent electrode, and the counter electrode (4) is formed on the inner surface of the other transparent substrate. ) Is formed, the two transparent substrates are placed to face each other, the peripheral edge is sealed with a sealant (6), and the EC dimmer medium (5) according to the present invention is enclosed inside.

上記の透明基板(1)、透明電極(2)、対向電極
(4)およびEC層(3)は、従来のEC調光体に一般的に
使用されているものを任意に使用すればよい。
As the transparent substrate (1), the transparent electrode (2), the counter electrode (4) and the EC layer (3), those generally used in conventional EC dimmers may be arbitrarily used.

透明基板としては透明なガラス板、プラスチック板また
はこれらの積層板等が例示されるが、一般式[I]〜
[IV]で表わされる化合物は、従来のアルコール類等の
媒体に比べて溶剤性が高いので、これに溶解もしくは膨
潤したり、これによって不透明化を生ずるようなプラス
チック板の使用は避けるべきである。また、窓や間仕切
等として実用上十分な強度を有する厚さの透明基板を使
用する。
Examples of the transparent substrate include a transparent glass plate, a plastic plate, or a laminated plate thereof, and the like.
Since the compound represented by [IV] has a higher solvent property than the conventional medium such as alcohols, it is necessary to avoid the use of a plastic plate which dissolves or swells in the medium or causes opacity. . Further, a transparent substrate having a thickness having practically sufficient strength is used as a window or partition.

透明電極としてはIn2O3−SnO2、SnO2、Au等の透明で電
解質に浸食されない電極が例示される。透明電極は前記
透明基板上に蒸着、スパッタリング、フィルム貼着等の
方法によって形成させればよい。
Examples of the transparent electrode include transparent electrodes such as In 2 O 3 —SnO 2 , SnO 2 and Au that are not corroded by the electrolyte. The transparent electrode may be formed on the transparent substrate by a method such as vapor deposition, sputtering, and film sticking.

対向電極は前記の透明電極と同様の素材であってもよい
が、細線状の金属やカーボン等であってもよい。
The counter electrode may be made of the same material as that of the above-mentioned transparent electrode, but may be a thin wire metal or carbon.

EC層としてはWO3、MoO3、TiO2またはIr2O3等の蒸着膜等
が適当であるが、これに限定されるものではない。
As the EC layer, a vapor deposition film of WO 3 , MoO 3 , TiO 2 or Ir 2 O 3 is suitable, but the EC layer is not limited to this.

シール材としてはエポキシ樹脂、シリコン樹脂、フッ素
樹脂、アクリル樹脂等が例示される。
Examples of the sealing material include epoxy resin, silicon resin, fluororesin, acrylic resin and the like.

本発明によるEC調光体用媒体は前記一般式で表わされる
化合物に適当な支持電解質を溶解して用いる。支持電解
質としては前述のような公知の電解質、例えば塩化リチ
ウム、フッ化リチウム、ヨウ化リチウム等のハロゲン化
リチウム、過塩素酸リチウム、過塩素酸ナトリウム等の
過塩素酸アルカリ金属等を適宜使用すればよい。使用量
は通常10-3モル/以上、好ましくは0.1〜1.0モル/
である。
The EC dimmer medium according to the present invention is used by dissolving a suitable supporting electrolyte in the compound represented by the above general formula. As the supporting electrolyte, a known electrolyte as described above, for example, lithium halide such as lithium chloride, lithium fluoride, or lithium iodide, lithium perchlorate, alkali metal perchlorate such as sodium perchlorate, or the like may be appropriately used. Good. The amount used is usually 10 −3 mol / or more, preferably 0.1 to 1.0 mol /
Is.

本発明によるEC調光体用媒体には所望により他の添加
剤、例えば着色剤、粘度調整剤、凍結防止剤、希釈剤等
を適宜配合してもよい。
If desired, other additives such as colorants, viscosity modifiers, antifreezing agents, and diluents may be added to the medium for EC dimmer according to the present invention.

以下、本発明を実施例によって説明する。Hereinafter, the present invention will be described with reference to examples.

実施例1 透明ガラス基板の内面にIn2O3−SnO2透明電極を真空蒸
着させ、該電極上にWO3を真空蒸着させた。別の透明ガ
ラス基板の内面にIn2O3−SnO2を真空蒸着させた。
The In 2 O 3 -SnO 2 transparent electrode on the inner surface of Example 1 a transparent glass substrate was vacuum vapor deposition, and the WO 3 was vacuum deposited on the electrode. The In 2 O 3 -SnO 2 was vacuum deposited on the inner surface of another transparent glass substrate.

2枚の透明基板を電極面が内面になるように相対置さ
せ、周縁部をエポキシ樹脂でシールして透明セルを調製
した。この透明セルの内部へ、5−エチル−5−エトキ
シメチル−1,3−ジオキサン−2−オンに過塩素酸リチ
ウムを溶解させた溶液(0.3モル/)を注入し、注入
口を封止してEC調光体を得た。
Two transparent substrates were placed relative to each other so that the electrode surface was the inner surface, and the peripheral edge was sealed with an epoxy resin to prepare a transparent cell. A solution (0.3 mol /) in which lithium perchlorate was dissolved in 5-ethyl-5-ethoxymethyl-1,3-dioxan-2-one was injected into this transparent cell, and the injection port was sealed. I got an EC dimmer.

得られたEC調光体をウェザーメーターで300時間照射
し、照射前後の消色時の透過率を比較した。結果を以下
の表−4に示す。
The EC dimmer thus obtained was irradiated with a weather meter for 300 hours, and the transmittances at the time of erasing before and after irradiation were compared. The results are shown in Table 4 below.

また、このEC調光体に1Vの電圧を印加したところ約1分
間で透過率が20%に低下し、消色も約1分間で完了し
た。
When a voltage of 1 V was applied to this EC dimmer, the transmittance dropped to 20% in about 1 minute, and the erasing was completed in about 1 minute.

実施例2 5−エチル−5−エトキシメチル−1,3−ジオキサン−
2−オンの代わりに、4−(ピロリジノメチル)−1,3
−ジオキソラン−2−オンを使用する以外は実施例1と
同様にして照射前後の透過率を比較した。結果を表−4
に示す。
Example 2 5-Ethyl-5-ethoxymethyl-1,3-dioxane-
4- (pyrrolidinomethyl) -1,3 instead of 2-one
The transmittance before and after irradiation was compared in the same manner as in Example 1 except that -dioxolan-2-one was used. The results are shown in Table-4.
Shown in.

また、得られたEC調光体に1Vの電圧を印加したところ、
約1分間で透過率が20%に低下し、消色も約1分間で完
了した。
When a voltage of 1 V was applied to the obtained EC dimmer,
The transmittance decreased to 20% in about 1 minute, and the color erasing was completed in about 1 minute.

比較例 5−エチル−5−エトキシメチル−1,3−ジオキサン−
2−オンの代わりにn−ブタノールを用いる以外は実施
例1と同様にして照射前後の透過率を比較した。結果を
表−4に示す。
Comparative Example 5-Ethyl-5-ethoxymethyl-1,3-dioxane-
The transmittances before and after irradiation were compared in the same manner as in Example 1 except that n-butanol was used instead of 2-one. The results are shown in Table-4.

また、得られたEC調光体に1Vの電圧を印加したところ、
約2分間で透過率が20%に低下し、消色も約2分間で完
了した。
When a voltage of 1 V was applied to the obtained EC dimmer,
The transmittance decreased to 20% in about 2 minutes, and the color erasing was completed in about 2 minutes.

発明の効果 本発明による媒体を用いたEC調光体は着消色の応答速度
が速いだけでなく、優れた耐候性を有するために長時間
の光照射による光透過率の低下が小さい。
EFFECTS OF THE INVENTION The EC dimmer using the medium according to the present invention not only has a fast response speed for coloration and decoloration, but also has excellent weather resistance, so that the decrease in light transmittance due to light irradiation for a long time is small.

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

第1図は本発明によるEC調光体用媒体を用いたEC調光体
の一態様を示す模式的横断面図である。(1)は透明基
板、(2)は透明電極、(3)はEC層、(4)は対向電
極、(5)はEC調光体用媒体、(6)はシール材を示
す。
FIG. 1 is a schematic cross-sectional view showing one embodiment of an EC dimmer using the medium for an EC dimmer according to the present invention. (1) is a transparent substrate, (2) is a transparent electrode, (3) is an EC layer, (4) is a counter electrode, (5) is an EC dimmer medium, and (6) is a sealant.

───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 FI 技術表示箇所 C07D 327/10 ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 6 Identification code Internal reference number FI technical display location C07D 327/10

Claims (1)

【特許請求の範囲】[Claims] 【請求項1】一般式[I]: (式中、R1は水素原子またはメチル基を示し、R2は炭素
原子数1〜4の側鎖を有していてもよいアルキル基を示
し、Xは炭素原子または硫黄原子を示す) で表される化合物または一般式[II]: [式中、Xは前記と同意義であり、Yは一般式[II
I]: −O−R2 [III] (式中、R2は前記と同意義である) で表される基または一般式[IV]: (式中、R3およびR4はそれぞれ独立して炭素原子数1〜
4の飽和また不飽和の側鎖を有してもよいアルキル基、
両者合して酸素原子を有することもある5員環もしくは
6員環を示す)で示される基を示す] で表わされる化合物を含有するエレクトロクロミック調
光体用媒体。
1. A general formula [I]: (In the formula, R 1 represents a hydrogen atom or a methyl group, R 2 represents an alkyl group which may have a side chain having 1 to 4 carbon atoms, and X represents a carbon atom or a sulfur atom.) Compound represented or general formula [II]: [In the formula, X has the same meaning as described above, and Y represents the general formula [II
I]: —O—R 2 [III] (wherein R 2 has the same meaning as described above) or a general formula [IV]: (In the formula, R 3 and R 4 are each independently a carbon atom number of 1 to 1.
An alkyl group which may have a saturated or unsaturated side chain of 4,
And a compound represented by the formula [4], which represents a 5-membered ring or a 6-membered ring which may have an oxygen atom in combination with each other.] For an electrochromic dimmer.
JP20036686A 1986-08-26 1986-08-26 Electrochromic dimmer medium Expired - Fee Related JPH0772269B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP20036686A JPH0772269B2 (en) 1986-08-26 1986-08-26 Electrochromic dimmer medium

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP20036686A JPH0772269B2 (en) 1986-08-26 1986-08-26 Electrochromic dimmer medium

Publications (2)

Publication Number Publication Date
JPS6356590A JPS6356590A (en) 1988-03-11
JPH0772269B2 true JPH0772269B2 (en) 1995-08-02

Family

ID=16423109

Family Applications (1)

Application Number Title Priority Date Filing Date
JP20036686A Expired - Fee Related JPH0772269B2 (en) 1986-08-26 1986-08-26 Electrochromic dimmer medium

Country Status (1)

Country Link
JP (1) JPH0772269B2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5514798A (en) * 1993-06-02 1996-05-07 Gilead Sciences, Inc. Method and cyclic carbonates for nucleotide analogues

Also Published As

Publication number Publication date
JPS6356590A (en) 1988-03-11

Similar Documents

Publication Publication Date Title
US4671619A (en) Electro-optic device
US5611966A (en) Electrochemichromic solutions, processes for preparing and using the same, and devices manufacturing with the same
JP2726660B2 (en) Variable reflectivity rearview mirror for automobile
KR100642944B1 (en) Color-stabilized electrochromic devices
US5233461A (en) Methods for sealing electrochromic devices and devices manufactured thereby
US7046418B2 (en) Reversible electrodeposition devices and associated electrochemical media
US7884995B2 (en) Electrochromic device having an improved fill port plug
EP0531143A2 (en) Electrochemichromic solutions, processes for preparing and using the same, and devices manufactured with the same
US20020008897A1 (en) Anodic electrochromic materials having a solublizing moiety
JPS63106731A (en) Dimmer body
JPH0217093B2 (en)
US20020027700A1 (en) Electrochromic display device having high edge sharpness
JPH0772269B2 (en) Electrochromic dimmer medium
JP3472810B2 (en) Wet electrochromic device using room temperature molten salt
JP2003149686A (en) Semi-transparent mirror transmissivity variable element
JPH0772270B2 (en) Electrochromic dimmer medium
JPH0781136B2 (en) Electrochromic dimmer medium
JP2004029433A (en) Electrochromic element
JPH07216349A (en) Electrochemichromic solution, its preparation, method of using it, and device produced by using it
JPS6132036A (en) Electrochromic device
JPS63106732A (en) Electrochromic element
JP2002357852A (en) Electrochromic element
JPH0243104B2 (en)
JPS6063272A (en) Cell type electrochromic display element
JPS6132037A (en) Electrochromic device

Legal Events

Date Code Title Description
R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

LAPS Cancellation because of no payment of annual fees