KR20100025876A - Organic electrochromic compounds and electrochromic device containing the same - Google Patents
Organic electrochromic compounds and electrochromic device containing the same Download PDFInfo
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Abstract
Description
본 발명은 유기 전기변색 화합물 및 이를 포함하는 전기변색 소자에 관한 것으로서, (1) 전기변색 특성을 가지는 부분, (2) 전도성 특성을 가지는 부분, 및 (3) 전기변색 부분과 전도성 부분을 연결해 주는 구조로 이루어진 것을 특징으로 한다. 본 발명의 유기 전기변색 화합물은 전압 인가 시 기존의 유기 전기변색 화합물과 비슷한 응답속도를 보여주지만, 더욱 우수한 물질의 안정성, 전기 변색 응답 속도 및 전기 변색 지속성을 나타내는 특성이 있다.The present invention relates to an organic electrochromic compound and an electrochromic device comprising the same, comprising (1) a portion having an electrochromic characteristic, (2) a portion having a conductive characteristic, and (3) connecting the electrochromic portion and a conductive portion It is characterized by consisting of a structure. The organic electrochromic compound of the present invention shows a response speed similar to that of the existing organic electrochromic compound when voltage is applied, but has characteristics such as better material stability, electrochromic response speed, and electrochromic persistence.
전기변색이란 전기화학적 산화·환원 반응에 의해 물질의 색을 가역적으로 조절하는 것으로서, 산화 또는 환원 시 수반되는 전자 이동으로 인해 에너지 흡수 변화에 따라 색깔의 변화를 가져오는 것이다. 전도성 고분자의 전기변색 성질은 스마트 윈도우(smart window)라 불리는 전기변색 유리창이나 투과하는 빛을 조절하는 장치, 차세대 저전압용 디스플레이 등에 응용될 수 있기 때문에 많은 연구가 진행 중이다. 그 중 전기변색 화합물과 전도성 화합물이 결합된 전기변색 화합물, 즉 두 기능을 모두 가지고 있는 전기변색 화합물(bifunctional redox dye)은 전자 이 동의 수월성과 안정성, 그리고 전기 변색 특성의 우수성 등으로 많은 연구가 진행 중이다. Electrochromic is reversible control of the color of a material by electrochemical oxidation and reduction reactions. The color change is caused by changes in energy absorption due to electron transfer accompanying oxidation or reduction. Electrochromic properties of conductive polymers are being researched because they can be applied to electrochromic glass windows called smart windows, devices for controlling transmitted light, and displays for next-generation low voltage displays. Among them, electrochromic compounds in which electrochromic compounds and conductive compounds are combined, that is, bifunctional redox dyes having both functions, have been studied for their ease of electron transfer, stability, and excellent electrochromic properties. In the process.
그러나, 전기변색 화합물과 전도성 화합물의 연결 합성 방법이 복잡하고 어려우며, 또한 전자 이동과 에너지 흡수 변화의 우수성을 확보하기 위해서는 전기변색 화합물과 전도성 화합물의 연결 화합물에 대한 보다 많은 연구가 요구되었다.However, the connection synthesis method of the electrochromic compound and the conductive compound is complicated and difficult, and further studies on the linking compound of the electrochromic compound and the conductive compound have been required in order to secure the excellent electron transfer and energy absorption change.
이와 관련하여, 미국 특허 등록 제 US-6262832호, 제 US-6853472호, 제 US 2002/0015214 A1에서는 전기변색 화합물과 전도성 화합물을 모두 포함하고 연결되어 있는 것을 특징으로 하는 전기변색 화합물에 대하여 기재하고 있으나, 연결부위가 일반적인 알킬기이며, 또한 합성 방법이 어렵고 복잡하며, 전자 이동과 전기변색 특성, 그리고 안정성을 향상시키는 연결 화합물에 대한 연구가 미비하다는 문제점이 있다. In this regard, US Patent Nos. US-6262832, US-6853472, US 2002/0015214 A1 describe an electrochromic compound which includes and is connected to both the electrochromic compound and the conductive compound. However, there is a problem in that the linking site is a general alkyl group, and the synthesis method is difficult and complicated, and research on linking compounds for improving electron transfer, electrochromic properties, and stability is insufficient.
이에, 본 발명자들은 전기변색 화합물과 전도성 화합물이 모두 포함되어 있는 것을 특징으로 하는 전기변색 화합물의 전기변색 특성 향상을 위해 연구한 결과, 전기변색 화합물과 전도성 화합물을 연결시켜 주는 화합물로서, 전자가 풍부한 유기물질을 이용하여 전자의 이동이 수월하게 함으로써 변색 응답 속도나 안정성에 우수한 특성이 있다는 것을 알게 되어 발명을 완성하게 되었다.Accordingly, the present inventors have studied to improve the electrochromic properties of the electrochromic compound, characterized in that both the electrochromic compound and the conductive compound, as a compound that connects the electrochromic compound and the conductive compound, rich in electrons By using an organic material to facilitate the movement of electrons, the present inventors have found that the discoloration response speed and stability are excellent.
따라서, 본 발명의 목적은 우수한 전기변색 특성을 나타내는 전기변색 화합물과 전도성 화합물을 모두 포함하는 것을 특징으로 하는 전기변색 화합물과 상기 전기변색 화합물을 이용한 전기변색 소자에 관한 것이다.Accordingly, an object of the present invention relates to an electrochromic compound and an electrochromic device using the electrochromic compound, which include both an electrochromic compound and a conductive compound exhibiting excellent electrochromic properties.
본 발명은 하기 화학식 1로 표시되는 환원성 전기변색 화합물 및 하기 화학식 2로 표시되는 전도성 화합물을 모두 포함하는 것을 특징으로 하는 전기변색 화합물을 제공한다. 더 나아가, 상기 전기변색 화합물을 포함하는 전기변색 소자를 제공한다.The present invention provides an electrochromic compound comprising both a reducing electrochromic compound represented by Formula 1 and a conductive compound represented by Formula 2 below. Furthermore, it provides an electrochromic device comprising the electrochromic compound.
상기 화학식 1에서 A- 및 B- 는 각각 독립적으로 할라이드 이온, ClO4 -, BF4 -, PF6 -, AsF6 -, SbF6 -, CHCOO-, CH3(C6H4)SO3 -, CF3SO3 -, (CF3SO2)2N-, (CF3CF2SO2)2N-, (CF3SO2)3C-, (CF3SO2)2N-, 및 Li(CF3SO2)2N- 로부터 선택되는 음이온이다.In the formula 1 A - and B - it is independently a halide ion, ClO 4 -, BF 4 - , PF 6 -, AsF 6 -, SbF 6 -, CHCOO -, CH 3 (C 6 H 4) SO 3 - , CF 3 SO 3 -, ( CF 3 SO 2) 2 N -, (CF 3 CF 2 SO 2) 2 N -, (CF 3 SO 2) 3 C -, (CF 3 SO 2) 2 N -, and Li (CF 3 SO 2 ) 2 N − is an anion selected from.
상기 화학식 2에서 n은 각각 독립적으로 탄소수 1-4개의 알킬기 또는 탄화수소기이다. In Chemical Formula 2, n each independently represents an alkyl group having 1 to 4 carbon atoms or a hydrocarbon group.
구체적으로, 본 발명의 전기변색 화합물을 살펴보면, 하기 화학식 3 내지 5로 표시되는 사중극자(quadrupole)-바이피리디리움 유도체로 나타낸다.Specifically, looking at the electrochromic compound of the present invention, it is represented by a quadrupole (bidrupole) -bipyridium derivative represented by the following formula (3) -5.
상기 화학식 3, 4 및 5 에서, n 및 A- 는 화학식 1 및 2에서 정의한 바와 같다. 다만, n는 각각 독립적으로 탄소수가 2 내지 4인 알킬기가 바람직하며, 구체적으로는 에틸기, 프로필기 또는 부틸기가 있다. In Chemical Formulas 3, 4, and 5, n and A − are the same as defined in Chemical Formulas 1 and 2. However, n each independently represents an alkyl group having 2 to 4 carbon atoms, specifically, an ethyl group, a propyl group or a butyl group.
구체적으로, 상기 화학식 3의 화합물의 예로서 화학식 6 내지 8의 화합물을들 수 있다.Specifically, examples of the compound of Formula 3 may include a compound of Formulas 6 to 8.
상기 화학식 4의 화합물의 예로서 화학식 9 내지 11의 화합물을 들 수 있다.Examples of the compound of Formula 4 include compounds of Formulas 9 to 11.
상기 화학식 5의 화합물의 예로서 화학식 12 내지 14의 화합물을 들 수 있다.Examples of the compound of Formula 5 include a compound of Formulas 12 to 14.
또한, 본 발명은 상기 전기 변색 물질을 포함하여 제조되는 용액형 전기변색소자를 포함한다. In addition, the present invention includes a solution type electrochromic device prepared by including the electrochromic material.
본 발명의 전기 변색 소자는 투명이나 반사형의 기재상에 배치되며, 작업전극, 상대전극 및 전해질을 포함하여, 상기의 작업전극, 상대전극 및 전해질 중에 하나 이상이 본 발명의 전기 변색 물질을 포함한다. 이온전도성 전해질 용액은 전해질염이 용해된 용액을 사용하며, 상기의 전기변색물질을 용해시켜 이를 주입, 밀봉시키는 등의 방법으로 전기변색소자를 제작한다. The electrochromic device of the present invention is disposed on a transparent or reflective substrate, wherein at least one of the working electrode, counter electrode and electrolyte includes the electrochromic material of the present invention, including a working electrode, a counter electrode and an electrolyte. do. As the ion conductive electrolyte solution, a solution in which an electrolyte salt is dissolved is used, and an electrochromic device is manufactured by dissolving the electrochromic material, injecting and sealing the electrochromic material, and the like.
이 때, 상기 전기변색 전해질 혼합용액은 1) 상기 화학식 3 내지 5로 표시되는 전기변색 화합물 0.0005~10M; 2) 전해질염 0.001~10M, 바람직하게는 0.1~0.5M; 및 3) 용매를 함유하여 사용할 수 있다.At this time, the electrochromic electrolyte mixture solution is 1) the electrochromic compound 0.0005 ~ 10M represented by the formula 3 to 5; 2) 0.001-10 M, preferably 0.1-0.5 M electrolyte salt; And 3) a solvent.
상기 사중극자(quadrupole)-바이피리디리움의 사용량이 0.005M 미만이면 전기변색성이 보이지 않고, 15M을 초과하면 용액에서 화합물이 용출되는 문제가 발생하므로, 상기 범위를 유지하는 것이 바람직하다.If the amount of the quadrupole bipyridium is less than 0.005M, the electrochromic property is not seen. If the amount exceeds 15M, the compound is eluted from the solution. Therefore, it is preferable to maintain the above range.
이 때, 상기 전해질염은 당 분야에서 사용되는 일반적인 것으로 특별히 한정 하지는 않으나, 구체적으로 n-Bu4NClO4, n-Bu4NPF6, NaBF4, LiClO4, LiPF6, LiBF4, LiN(SO2C2F5)2, LiCF3SO3, C2F6LiNO4S2 , K4Fe(CN)6등을 사용할 수 있다. 이들 전해질염은 1종의 단일화합물 또는 2종 이상의 혼합물을 사용할 수 있다. 이러한 전해질염은 0.001~10M 범위로 사용되는 바, 상기 사용량이 0.005M 미만이면 전기변색성이 보이지 않고, 15M을 초과하면 용액에서 화합물이 용출되는 문제가 발생하므로, 상기 범위를 유지하는 것이 바람직하다.In this case, the electrolyte salt is a general one used in the art, but is not particularly limited. Specifically, n-Bu 4 NClO 4 , n-Bu 4 NPF 6 , NaBF 4 , LiClO 4 , LiPF 6 , LiBF 4 , LiN (SO 2 C 2 F 5 ) 2 , LiCF 3 SO 3 , C 2 F 6 LiNO 4 S 2 , K 4 Fe (CN) 6 and the like can be used. These electrolyte salts can use 1 type of single compound or 2 or more types of mixtures. Since the electrolyte salt is used in the range of 0.001 to 10M, electrochromic properties are not seen when the amount is less than 0.005M, and when the amount exceeds 15M, the compound is eluted from the solution. .
상기 용매는 당 분야에서 사용되는 비수성의 용매로 구체적으로 디클로메탄, 클로로포름, 아세토니트릴, 에틸렌 카보네이트(EC), 프로필렌 카보네이트(PC),테트라하이드로퓨란(THF), 뷰틸렌 카보네이트 등에서 선택된 1종 이상의 용매를 사용할 수 있다. The solvent is a non-aqueous solvent used in the art, specifically one selected from dichloromethane, chloroform, acetonitrile, ethylene carbonate (EC), propylene carbonate (PC), tetrahydrofuran (THF), butylene carbonate, and the like. The above solvent can be used.
이 외에 당 분야에서 일반적으로 사용되는 AO-30, AO-60, IRGANOX 1010, DH-43 등의 산화방지제 등을 함유시킬 수도 있는바, 이러한 첨가제는 이 분야에 통상적인 지식을 가진 자에 의하여 사용될 수 있다.In addition, it may contain antioxidants such as AO-30, AO-60, IRGANOX 1010, DH-43, and the like, which are commonly used in the art, and such additives may be used by those skilled in the art. Can be.
상술한 바와 같이, 본 발명에 따라 합성된 신규 유기 전기변색 화합물은 전기변색 소자에 적용되었을 때 전자 이동의 수월성에 의하여 변색 응답 속도가 빠르고, 전기변색 특성이 안정적으로 구현되며, 또한 우수한 색대비와 착색·소색 특성을 가진다.As described above, the novel organic electrochromic compound synthesized according to the present invention has a fast discoloration response speed due to the ease of electron transfer when applied to the electrochromic device, stable electrochromic properties, and excellent color contrast and It has coloring and discoloring characteristics.
이러한 전기변색 물질은 스마트 윈도우(smart window)라 불리는 전기변색 유 리창이나 투과하는 빛을 조절하는 장치, 차세대 저전압용 디스플레이 장치 등의 다방면에 응용이 가능하다. Such electrochromic materials can be applied to various fields such as electrochromic glass windows called smart windows, devices for controlling transmitted light, and next-generation low-voltage display devices.
이하의 실시예를 통하여 본 발명을 구체적으로 설명하는바, 하기의 실시예는 오로지 본 발명을 구체적으로 설명하기 위한 것으로 이들 실시예에 의해 본 발명을 한정하는 것은 아니다.Hereinafter, the present invention will be described in detail with reference to the following examples. The following examples are only for explaining the present invention in detail, and the present invention is not limited thereto.
실시예Example 1. 화학식 6의 화합물의 제조 1. Preparation of Compound of Formula 6
원넷(one-neck) 플라스크에 메톡시 페놀(5g, 40mmol)과 수산화나트륨 (3.22g, 80mmol)을 메탄올(100ml)에 녹였다. 이후 상온에서 디브로모에탄(22.65g, 120mmol)을 아세톤(80ml)에 녹여 플라스크에 빨리 넣어준 후, 3시간 동안 환류시켰다. 반응이 끝나면, 물과 메틸렌클로라이드로 추출하여 용매를 제거하여 1-(2-ㅂ 브로모-에톡시)-4-메톡시-벤젠을 수득하였다(수율 79%).In a one-neck flask, methoxy phenol (5 g, 40 mmol) and sodium hydroxide (3.22 g, 80 mmol) were dissolved in methanol (100 ml). Thereafter, dibromoethane (22.65 g, 120 mmol) was dissolved in acetone (80 ml) at room temperature and quickly put into a flask, followed by reflux for 3 hours. After the reaction, the mixture was extracted with water and methylene chloride to remove the solvent to give 1- (2- ㅂ bromo-ethoxy) -4-methoxy-benzene (yield 79%).
첫 반응 생성물(5g, 21.6 mmol)과 바이올겐(1.5g, 9.8 mmol)을 아세토나이트릴에 녹여 12시간 동안 환류시킨 후, 여과시키고, 이를 다시 물에서 NH4PF6로 염치환하여 최종 생성물을 수득하였다.The first reaction product (5 g, 21.6 mmol) and the biogen (1.5 g, 9.8 mmol) were dissolved in acetonitrile and refluxed for 12 hours, filtered and then again substituted with NH 4 PF 6 in water to obtain the final product. It was.
실시예Example 2. 화학식 7의 화합물의 제조 2. Preparation of Compound of Formula 7
디브로모에탄 대신 디브로모프로판을 사용하여 실시예 1와 동일한 방법으로 화학식 7의 화합물을 얻었다. Compound of formula 7 was obtained in the same manner as in Example 1 using dibromopropane instead of dibromoethane.
실시예Example 3. 화학식 8의 화합물의 제조 3. Preparation of Compound of Formula 8
디브로모에탄 대신 디브로모부탄을 사용하여 실시예 1와 동일한 방법으로 화학식 8의 화합물을 얻었다. Compound of formula 8 was obtained in the same manner as in Example 1 using dibromobutane instead of dibromoethane.
실시예Example 4. 화학식 9의 화합물의 제조 4. Preparation of Compound of Formula 9
원넥 플라스크에 아미노페놀(5g, 46mmol)과 파라포름알데히드(3.02g, 96 mmol)을 메탄올(100 ml)에 녹인 후, 수소화붕소나트륨(100 mmol)을 상온에서 천천히 적가해준 후, 2시간 동안 반응시켰다. 반응이 끝나면, 물과 에틸아세테이트로 추출하여 용매를 제거하여 N, N'-디메틸 아미노 페놀을 수득하였다(수율 75%).After dissolving aminophenol (5 g, 46 mmol) and paraformaldehyde (3.02 g, 96 mmol) in methanol (100 ml) in a one neck flask, sodium borohydride (100 mmol) was slowly added dropwise at room temperature, followed by reaction for 2 hours. I was. After the reaction, the mixture was extracted with water and ethyl acetate to remove the solvent to obtain N, N'- dimethyl amino phenol (yield 75%).
첫 반응 생성물(5g, 38mmol)과 수산화나트륨(2.2g, 57mmol)을 메탄올(100 ml)에 녹인 후, 디브로모에탄(14.3g, 76 mmol)을 아세톤(80ml)에 녹여 플라스크에 빨리 넣어준 후, 3시간 동안 환류시켰다. 반응이 끝나면 물과 메틸렌클로라이드로 추출하여 용매를 제거하여 1-(2-브로모-에톡시)-4-메톡시-벤젠을 수득하였다(수율 79%). 바이올겐(1.5g, 9.8mmol)을 아세토니트릴에 녹여 12시간 동안 환류시킨 후, 여과시키고, 이를 다시 물에서 NH4PF6로 염치환하여 최종 생성물을 수득하였다.The first reaction product (5 g, 38 mmol) and sodium hydroxide (2.2 g, 57 mmol) were dissolved in methanol (100 ml), then dibromoethane (14.3 g, 76 mmol) was dissolved in acetone (80 ml) and quickly put into a flask. Then, refluxed for 3 hours. After the reaction, the mixture was extracted with water and methylene chloride to remove the solvent to give 1- (2-bromo-ethoxy) -4-methoxy-benzene (yield 79%). Biogen (1.5 g, 9.8 mmol) was dissolved in acetonitrile and refluxed for 12 hours, and then filtered, which was again substituted with NH 4 PF 6 in water to obtain a final product.
실시예Example 5. 화학식 10의 화합물의 제조 5. Preparation of Compound of Formula 10
디브로모에탄 대신 디브로모프로판을 사용하여 실시예 4와 동일한 방법으로 화학식 10의 화합물을 얻었다.Compound of formula 10 was obtained in the same manner as in Example 4 using dibromopropane instead of dibromoethane.
실시예Example 6. 화학식 11의 화합물의 제조 6. Preparation of Compound of Formula 11
디브로모에탄 대신 디브로모부탄을 사용하여 실시예 4와 동일한 방법으로 화학식 11의 화합물을 얻었다. Compound of formula 11 was obtained in the same manner as in Example 4, using dibromobutane instead of dibromoethane.
실시예Example 7. 화학식 12의 화합물의 제조 7. Preparation of Compound of Formula 12
원넥 플라스크에 디아미노 벤젠(6g, 55mmol)과 클로로 아세트산(15.7g, 165 mmol)와 수산화나트륨(17.7g, 443mmol)을 물(200ml)에 녹인 후, 요오드나트륨(2.5 g, 1.65mmol)을 더 넣어준 후, 1시간 동안 환류시켰다. 반응이 끝나면 물과 에틸 아세테이트로 추출하여 용매를 제거하여 화합물을 수득하였다(수율 55%). 나머지 과정은 실시예 1 및 4의 과정과 동일하다.In a one neck flask, diamino benzene (6 g, 55 mmol), chloro acetic acid (15.7 g, 165 mmol) and sodium hydroxide (17.7 g, 443 mmol) were dissolved in water (200 ml), and then sodium iodine (2.5 g, 1.65 mmol) was added. After the addition, it was refluxed for 1 hour. After the reaction, the mixture was extracted with water and ethyl acetate to remove the solvent to give a compound (yield 55%). The rest of the procedure is the same as that of Examples 1 and 4.
실시예Example 8. 화학식 13의 화합물의 제조 8. Preparation of Compound of Formula 13
디브로모에탄 대신 디브로모프로판을 사용하여 실시예 7과 동일한 방법으로 화학식 13의 화합물을 얻었다. Compound of formula 13 was obtained in the same manner as in Example 7 using dibromopropane instead of dibromoethane.
실시예Example 9. 화학식 14의 화합물의 제조 9. Preparation of Compound of Formula 14
디브로모에탄 대신 디브로모프로판을 사용하여 실시예 7과 동일한 방법으로 화학식 14의 화합물을 얻었다. Compound of formula 14 was obtained in the same manner as in Example 7 using dibromopropane instead of dibromoethane.
실험예Experimental Example . 전기변색 소자의 전기변색 실험. Electrochromic Experiment of Electrochromic Device
제작한 전기변색소자에 0V에서 -2.0 V나 2.0 V로 인가전압을 변화시키면, 무색 투명에서 진한 파란색으로 색이 변한다. 인가 전압을 -2.0V에서 2.0V로 30초마다 바꾸면서 535nm에서 전체 흡광도 변화의 70%가 변하는데 걸리는 시간을 응답시간으로 측정하였다.When the applied voltage is changed from 0V to -2.0V or 2.0V in the fabricated electrochromic device, the color changes from colorless transparent to dark blue. The response time was measured by changing the applied voltage from -2.0V to 2.0V every 30 seconds to change 70% of the total absorbance change at 535 nm.
도 1은 실시예 3의 전기변색 소자의 소색 및 착색 상태의 사진이다. 1 is a photograph of the discolored and colored state of the electrochromic device of Example 3.
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