JPS6356589A - Medium for electrochromic dimmer - Google Patents

Medium for electrochromic dimmer

Info

Publication number
JPS6356589A
JPS6356589A JP61200365A JP20036586A JPS6356589A JP S6356589 A JPS6356589 A JP S6356589A JP 61200365 A JP61200365 A JP 61200365A JP 20036586 A JP20036586 A JP 20036586A JP S6356589 A JPS6356589 A JP S6356589A
Authority
JP
Japan
Prior art keywords
derivative
medium
thian
dioxa
side chain
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
Application number
JP61200365A
Other languages
Japanese (ja)
Other versions
JPH0781136B2 (en
Inventor
Osamu Kawabata
河端 治
Harushige Nakada
中田 晴繁
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 JP61200365A priority Critical patent/JPH0781136B2/en
Publication of JPS6356589A publication Critical patent/JPS6356589A/en
Publication of JPH0781136B2 publication Critical patent/JPH0781136B2/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Landscapes

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

Abstract

PURPOSE:To provide the titled medium containing a specific 1,3-dioxan-2-one (derivative) or 1,3-dioxa-2-thian-2-oxide (derivative), capable of dissolving additives and electrolytes to form a clear solution and having high chemical stability and excellent weather resistance. CONSTITUTION:The objective medium contains 1,3-dioxane-2-one (derivative) or 1,3-dioxa-2-thian-2-oxide of formula (X is C or S; R1-R6 are H or alkyl which may have 1-4C side chain). The groups R1-R6 in the formula are preferably >=3C alkyl having at least one side chain. An electrochromic dimmer prepared therefrom has high response of coloring and color distinction and keeps the light transmittance almost to the original level even after irradiation over a long period.

Description

【発明の詳細な説明】 産業上の利用分野 本発明は、エレクトロクロミック物質(EC)を使用し
たElf光体用電解液に関するものである。
DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to an electrolyte for an Elf light body using an electrochromic substance (EC).

従来の技術 および 発明が解決しようとする問題点 光線を遮蔽するための調光体として、従来のブラインド
やカーテンに代る新しい電気光学的作用を利用したEC
U光体が注目されている。
Problems to be solved by conventional techniques and inventions EC that uses a new electro-optical function to replace conventional blinds and curtains as a light control body for blocking light rays.
U-light bodies are attracting attention.

これは透明電極上にエレクトロクロミック物質層を形成
した透明基板と、対向電極を形成した透明基板とを電解
質を介して積層してなる調光体であるが、これに用いる
電解液のイオン伝導性を改良した有機物電解質としては
、酸または塩基を含有した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
、過塩素酸塩を含有したプロピレンカーボネート等が提
案されている。
This is a light control body made by laminating a transparent substrate on which an electrochromic material layer is formed on a transparent electrode, and a transparent substrate on which a counter electrode is formed, with an electrolyte interposed in between. As improved organic electrolytes, polyvinyl alcohol containing acid or base, polyacrylamide, ethylene glycol, polystyrene, propylene carbonate containing perchlorate, etc. have been proposed.

しかしながら、ECR光体は、車両、自動車、航空機用
窓等、太陽光、温度変化に対する長期間の耐候性が要求
されるため溶剤自体が安定であり、各種の機能向上のた
めに添加される添加剤等の溶質を均一に溶解させること
が不可欠の要素となる。
However, since ECR light materials are required to have long-term weather resistance against sunlight and temperature changes in vehicles, automobiles, aircraft windows, etc., the solvent itself is stable, and additives are added to improve various functions. It is essential to uniformly dissolve solutes such as agents.

例えば応答性改善のために各種のキレート化剤、消色性
を改善す4含ヨウ素化合物、着色時の応答性を改善する
トリクロル酢酸、ベンゼンスルホン酸等が提案されてお
り、溶質としては、過塩素リチウム、塩化リチウム、ホ
ウフッ化リチウム、過塩素ナトリウムが用いられている
For example, various chelating agents have been proposed to improve responsiveness, tetraiodine-containing compounds to improve decolorization, trichloroacetic acid and benzenesulfonic acid to improve responsiveness during coloring, etc. Lithium chloride, lithium chloride, lithium borofluoride, and sodium perchloride are used.

本発明はこれらの機能改善のために添加される化合物な
らびに電解質を透明に溶解する能力を有し、化学的に安
定で、長期間耐候性のある溶媒を開発する目的でなされ
たものである。
The purpose of the present invention is to develop a chemically stable and long-term weather-resistant solvent that has the ability to transparently dissolve compounds and electrolytes added to improve these functions.

本発明は一般式[I]: [式中、Xは炭素または硫黄、R,、R2,r(3゜R
4,RsおよびRt+はそれぞれ独立して水素または炭
素数1〜4の側鎖を有することもあるアルキル基を示す
]で表わされる化合物を含汀するエレクトロクロミック
調光体用媒体として用いることにより上記問題を解決し
た。
The present invention relates to the general formula [I]: [wherein, X is carbon or sulfur, R,, R2, r (3゜R
4, Rs and Rt+ each independently represent hydrogen or an alkyl group which may have a side chain having 1 to 4 carbon atoms] By using the above as a medium for an electrochromic light control body, Problem solved.

本発明で用いる一般式JIEで示される1、3−ジオキ
サン−2−オンおよびその誘導体、および1.3−ジオ
キサ−2−チアン−2−オキントおよびその誘導体は従
来ECJll光体用媒体として全く用いられたことがな
いが、紫外線に対して安定であり、ECg光体の支持電
解物質として広く用いられている。過塩素酸リチウム、
塩化リチウム、フッ化リチウム、ヨウ化リチウム等に対
する良溶剤であって高い誘電率を示す。
1,3-dioxan-2-one and its derivatives represented by the general formula JIE used in the present invention, and 1,3-dioxa-2-thian-2-ochinto and its derivatives have never been used as a medium for ECJll light bodies. Although it has never been studied, it is stable to ultraviolet light and is widely used as a supporting electrolyte in ECg light bodies. lithium perchlorate,
It is a good solvent for lithium chloride, lithium fluoride, lithium iodide, etc. and exhibits a high dielectric constant.

本発明に用いられる前記化合物のR,−R,はそれぞれ
独立して水素または炭素数1〜4の側鎖を有することも
あるアルキル基であるが、具体的には例えば4−イソプ
ロピル−5,5−ジメチル−!、3−ジオキサンー2−
オン、4−ターシャリ−ブチル−5,5−ジメチル−1
,3−ジオキサン−2−オン、4−イソプロピル−1,
3−ジオキサン−2−オン、4−イソプロピル−5−メ
チル−1,3−ジオキサン−2−オン等、および4−イ
ソプロピル−5,5−ツメチル−1,3−ジオキサ−2
−チアン−2−オキシド、4−イソプロピル−5−メチ
ル−1,3−ジオキサ−2−チアン−2−オキシド等の
少なくと乙−つの側鎖を有する炭素数3以上のアルキル
基を有する化合物が好ましい。これらの側鎖を有するア
ルキル基を有する化合物は低い凝固点を有するため、窓
ガラス、フロントガラス等屋外で使用される場合、冬期
凝結することがない。しかしながら比較的高い融点のも
のであっても、これを他の溶剤、例えばブタノール、イ
ソプロパツールあるいは前述の低融点カーボネート化合
物等と併用して使用することかできる。
R and -R in the compound used in the present invention are each independently hydrogen or an alkyl group that may have a side chain of 1 to 4 carbon atoms, and specifically, for example, 4-isopropyl-5, 5-dimethyl-! , 3-dioxane-2-
4-tert-butyl-5,5-dimethyl-1
, 3-dioxan-2-one, 4-isopropyl-1,
3-dioxan-2-one, 4-isopropyl-5-methyl-1,3-dioxan-2-one, etc., and 4-isopropyl-5,5-tmethyl-1,3-dioxa-2
Compounds having an alkyl group having at least two side chains and having three or more carbon atoms, such as -thian-2-oxide, 4-isopropyl-5-methyl-1,3-dioxa-2-thian-2-oxide, etc. preferable. Since these compounds having an alkyl group having a side chain have a low freezing point, they do not condense in winter when used outdoors such as on window glass or windshield. However, even those with relatively high melting points can be used in combination with other solvents such as butanol, isopropanol, or the low melting point carbonate compounds mentioned above.

本発明ECJI光体用媒体は例えば第1図に示すごとく
して使用してもよい。即ち、2枚の透明基板(1)の一
方の内面に透明電極(2)を設け、さらに透明基板の内
面にEC層(3)を配し、他方の透明基板内面に対向電
極(4)を設け、両電極間に本発明のEC調光用媒体(
5)を封入する。(6)は絶縁性のシール材である。
The ECJI optical medium of the present invention may be used, for example, as shown in FIG. That is, a transparent electrode (2) is provided on the inner surface of one of two transparent substrates (1), an EC layer (3) is arranged on the inner surface of the transparent substrate, and a counter electrode (4) is provided on the inner surface of the other transparent substrate. The EC dimming medium of the present invention (
5) Enclose. (6) is an insulating sealing material.

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調光体に一般に使用
されているものを任愈に使用すればよい。
The above transparent substrate (1), transparent electrode (2), counter electrode (4)
) and the EC layer (3), those commonly used in conventional EC light control bodies may be used as desired.

例えば透明基板はガラス、透明プラスチック等であるか
、本発明化合物は従来のアルコール類に比べ溶剤性が高
いため、これに溶解、膨潤、不透明化を生ずるプラスチ
ックは避けるべ8である。透明電極としてはSnow、
IntOs  Snow、Au等が適当である。EC層
は三酸化タングステン系の蒸着膜等が適当である。もち
ろんこれに限定される乙のではない。対向電極は透明電
極と同じ素材の乙のであってよい。
For example, the transparent substrate should be glass, transparent plastic, etc., or plastics that dissolve, swell, or become opaque should be avoided since the compound of the present invention has higher solvent properties than conventional alcohols. As a transparent electrode, Snow,
IntOs Snow, Au, etc. are suitable. A suitable EC layer is a tungsten trioxide-based vapor deposited film. Of course, this is not the only option. The counter electrode may be made of the same material as the transparent electrode.

本発明EC調光体用媒体は支持電解質を溶解して用いる
。支持電解質は前述のごとき公知の電解質、例えば塩化
リチウム、フッ化すチウム、ヨウ化リチウム等のハロゲ
ン化すヂウム、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ることができ
る。使用量は10−3モル/Q以」二、好ましくは0.
1−1.0モル/Qである。
The medium for the EC light control body of the present invention is used by dissolving the supporting electrolyte. As the supporting electrolyte, known electrolytes such as those mentioned above, such as sodium halides such as lithium chloride, sulfur fluoride, and lithium iodide, and alkali metal perchlorates such as lithium perchlorate and sodium perchlorate, may be used as appropriate. can. The amount used is 10-3 mol/Q or more, preferably 0.
1-1.0 mol/Q.

本発明ECFI光体用媒体は所望ならば他の添加剤、例
えば着色剤、粘度調整剤、凍結防止剤等を適宜配合して
もよい。
If desired, the ECFI light medium of the present invention may contain other additives, such as colorants, viscosity modifiers, anti-freeze agents, and the like.

以下、実施例をあげて説明する。Examples will be described below.

実施例1 ガラス基板上にIntOs  SnO,透明電極とWO
3を真空蒸着した。別にガラス基板上にInt03−S
nO,のみを真空蒸着した透明板を調製し両者を対向し
て周囲をエポキシ樹脂でシールし透明セルを調製した。
Example 1 IntOs SnO, transparent electrode and WO on a glass substrate
3 was vacuum deposited. Int03-S separately on a glass substrate
A transparent plate on which only nO was vacuum-deposited was prepared, and the two plates were placed facing each other and the periphery was sealed with epoxy resin to prepare a transparent cell.

別に4−イソプロピル−5,5−ジメチル−1゜3−ジ
オキサン−2−オン (誘電率81.凝固点−42℃、沸点127℃(2,5
mmHg))にLiC10* 0.2モル/12を加え
、これを前記透明セル中に注入し、注入口を封止してE
C調光体を得た。
Separately, 4-isopropyl-5,5-dimethyl-1゜3-dioxan-2-one (dielectric constant 81, freezing point -42℃, boiling point 127℃ (2,5
0.2 mol/12 of LiC10* was added to mmHg)), injected into the transparent cell, the injection port was sealed, and E
A C light control body was obtained.

上記EC調光体をウェザ−メーターで300時間照射し
、照射前後の消色時の透過率を測定した。
The above EC light control body was irradiated with a weather meter for 300 hours, and the transmittance at the time of decolorization before and after irradiation was measured.

測定結果を表−■に示す。The measurement results are shown in Table-■.

またこのECM光体にtVの電圧を印加したところ約1
分で透過率が20%に変化し、かつ消色も約1分で完了
した。
Also, when a voltage of tV was applied to this ECM light body, approximately 1
The transmittance changed to 20% in 1 minute, and decolorization was completed in about 1 minute.

実施例2 媒体として4−イソプロピル−5,5−ジメチル−1,
3−ジオキサン−2−オンに代えて4−イソプロピル−
5,5−ジメチル−1,3−ジオキサ−2−チアン−2
−オキシド I (誘電率15.6、凝固点−13℃、沸点57〜60℃
(0,4n+mHg ))を用いる以外、実施例1と同
様にして照射前後の透過率を測定した。結果を表−1に
示す。
Example 2 4-isopropyl-5,5-dimethyl-1, as a medium
4-isopropyl-in place of 3-dioxan-2-one
5,5-dimethyl-1,3-dioxa-2-thian-2
-Oxide I (dielectric constant 15.6, freezing point -13℃, boiling point 57-60℃
Transmittance before and after irradiation was measured in the same manner as in Example 1 except that (0,4n+mHg)) was used. The results are shown in Table-1.

またこのEC調光体に1■の電圧を印加したところ、約
1公事で透過率が20%に低下し、かつ消色も約I公事
で完了した。
Furthermore, when a voltage of 1.5 cm was applied to this EC dimmer, the transmittance decreased to 20% after about 1 time, and color erasure was completed after about 1 time.

比較例 4−イソプロピル−5,5−ジメチル−1,3−ジオキ
サン−2−オンに代えてn−ブタノールを用いる以外実
施例1と同様にして照射前後の透過率を測定した。結果
を表−1に示す。
Comparative Example 4 The transmittance before and after irradiation was measured in the same manner as in Example 1 except that n-butanol was used in place of isopropyl-5,5-dimethyl-1,3-dioxan-2-one. The results are shown in Table-1.

またこのECff光体にIV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、かつ消色も約2分
間で完了した。
Also, when a voltage of IV was applied to this ECff light body,
The transmittance decreased to 20% in about 2 minutes, and decoloring was completed in about 2 minutes.

表−1 発明の効果 本発明EC調光体用媒体を用いると着消色の応答速度が
速く、かつ長時間の光照射による光の透過性の低下が少
ない。
Table 1 Effects of the Invention When the medium for an EC light control body of the present invention is used, the response speed of coloring/decoloring is fast, and the decrease in light transmittance due to long-term light irradiation is small.

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

第1図はEC調光体の一態様の模式的断面図である。 FIG. 1 is a schematic cross-sectional view of one embodiment of an EC light control body.

Claims (1)

【特許請求の範囲】 1、一般式[ I ]: ▲数式、化学式、表等があります▼[ I ] [式中、Xは炭素または硫黄、R_1、R_2、R_3
、R_4、R_5およびR_6はそれぞれ独立して水素
または炭素数1〜4の側鎖を有することもあるアルキル
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。
[Claims] 1. General formula [I]: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [I] [In the formula, X is carbon or sulfur, R_1, R_2, R_3
, R_4, R_5 and R_6 each independently represent hydrogen or an alkyl group which may have a side chain of 1 to 4 carbon atoms.
JP61200365A 1986-08-26 1986-08-26 Electrochromic dimmer medium Expired - Fee Related JPH0781136B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP61200365A JPH0781136B2 (en) 1986-08-26 1986-08-26 Electrochromic dimmer medium

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP61200365A JPH0781136B2 (en) 1986-08-26 1986-08-26 Electrochromic dimmer medium

Publications (2)

Publication Number Publication Date
JPS6356589A true JPS6356589A (en) 1988-03-11
JPH0781136B2 JPH0781136B2 (en) 1995-08-30

Family

ID=16423090

Family Applications (1)

Application Number Title Priority Date Filing Date
JP61200365A Expired - Fee Related JPH0781136B2 (en) 1986-08-26 1986-08-26 Electrochromic dimmer medium

Country Status (1)

Country Link
JP (1) JPH0781136B2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005228721A (en) * 2004-01-14 2005-08-25 Mitsubishi Chemicals Corp Nonaqueous electrolyte for lithium ion secondary battery and lithium ion secondary battery

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005228721A (en) * 2004-01-14 2005-08-25 Mitsubishi Chemicals Corp Nonaqueous electrolyte for lithium ion secondary battery and lithium ion secondary battery
JP4569128B2 (en) * 2004-01-14 2010-10-27 三菱化学株式会社 Non-aqueous electrolyte for lithium ion secondary battery and lithium ion secondary battery

Also Published As

Publication number Publication date
JPH0781136B2 (en) 1995-08-30

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