KR100965229B1 - Method of novel electrochromic viologens derivatives and green electrochromic element using the same method - Google Patents
Method of novel electrochromic viologens derivatives and green electrochromic element using the same method Download PDFInfo
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Abstract
본 발명은 전기변색 시 다양한 색 구현이 가능한 신규 비올로겐 유도체 제조와 이를 포함하여 전기변색 소자화 하였을때 전압 인가 시 green 색을 띄는 전기변색 소자 제조에 관한 것이다. 본 발명의 전기변색성 비올로겐 유도체는 2,2′bipyridyl을 이용하여 제조되며, 합성이 간단하고 전기변색 소자화 하였을 때 일반적으로 비올로겐 유도체는 Blue 또는 Violet 색을 띄는데 비해 본 발명에서는 green 색을 띄는 장점이 있다.The present invention relates to the production of a novel viologen derivative capable of realizing a variety of colors when electrochromic and electrochromic device having a green color when voltage is applied when the electrochromic device including the same. The electrochromic viologen derivatives of the present invention are prepared using 2,2′bipyridyl, and the synthesis is simple and when the electrochromic device is generally used, the viologen derivatives have a blue or violet color. There is a distinct advantage to color.
전기변색, 비올로겐, 전기변색소자, Green, 2,2′bipyridyl Electrochromic, viologen, electrochromic device, Green, 2,2′bipyridyl
Description
본 발명은 전기변색성을 갖는 신규한 비올로겐 유도체 및 상기의 비올로겐 유도체를 적용하여 전기변색시 녹색 계열의 색상을 띄는 전기변색 소자에 관한 것이다.The present invention relates to a novel viologen derivative having electrochromic properties and an electrochromic device having a green-based color when electrochromic by applying the viologen derivative.
본 발명의 전기변색성 비올로겐 유도체는 합성이 쉽고 간단하며 전기변색 소자화 하였을 때 전압 인가 시 기존의 비올로겐 유도체보다 다양한 색상을 구현할 수 있는 장점이 있다.The electrochromic viologen derivative of the present invention is easy and simple to synthesize, and when electrochromic device is applied, there is an advantage that various colors can be realized than the existing viologen derivative when voltage is applied.
전기변색이란 전기화학적 반응에 의하여 물질의 광학적 성질이 변하는 현상이며, 전기화학적으로 물질의 전자 상태나 구조가 변화됨으로써 물질의 고유색 또는 광투과도가 달라질 수 있다. 이러한 전기변색현상을 나타내는 물질은 비올로겐, 페로센, 페노티아진 등의 유기물질, WO3, NiOxHy, LiNiO2, Nb2O5, V2O5, TiO2, MoO3 등의 무기금속산화물 및 PODOT, 폴리피롤, 폴리아닐린, 폴리아줄렌, 폴리티오펜, 폴리피리딘, 폴리인돌, 폴리카바졸, 폴리아진, 폴리퀴논 등의 전도성 고분자 등이 있다. Electrochromism is a phenomenon in which the optical properties of a material are changed by an electrochemical reaction, and the intrinsic color or light transmittance of the material may be changed by changing the electronic state or structure of the material electrochemically. Materials exhibiting such electrochromic phenomena include organic materials such as viologen, ferrocene and phenothiazine, and inorganic metal oxides such as WO 3 , NiOxHy, LiNiO 2 , Nb 2 O 5 , V 2 O 5 , TiO 2 , and MoO 3 . And conductive polymers such as PODOT, polypyrrole, polyaniline, polyazulene, polythiophene, polypyridine, polyindole, polycarbazole, polyazine and polyquinone.
그 중 비올로겐은 쉽고 저렴하게 합성이 가능하여 1970년대부터 많이 연구되어 왔지만, 전도성 고분자에 비해 다중색 구현이 어렵고, 안정성과 메모리 효과가 떨어지고 응답성이 느린 단점으로 인해 신규 전기변색 비올로겐 유도체 개발이 답보 상태에 있다.Among them, viologen has been studied a lot since the 1970s because it can be easily and inexpensively synthesized. However, new electrochromic viologen is difficult due to the disadvantages of multi-color implementation, inferior stability and memory effect, and slow response. Derivative development is stale.
전기변색 현상이 알려진 것은 1961년이지만, 다중색의 구현이 어렵고, 발색 및 소색의 속도가 느리며, 완전 소색이 잘 안되고, 안정성이 떨어져 발색-소색을 반복하면 쉽게 망가지는 단점들로 인하여 아직까지 실용화되어 상업적으로 대량 생산되는 전기변색 소자는 거의 없다.The electrochromic phenomenon was known in 1961, but due to the disadvantages that it is difficult to implement multiple colors, the speed of color development and discoloration is slow, complete discoloration is poor, and stability is poor, it is easily broken by repeated color-bleaching. There are few commercially available electrochromic devices.
전기변색 소자는 일반적으로 환원전극, 산화전극, 전해질 및 전기변색물질로 이루어지며, 전기변색물질은 한쪽 또는 양쪽 전극 위에 막 형태로 형성되거나, 전해질 내에 포함되기도 한다. 전기변색소자에 전장을 인가하면 전기적 산화환원 반응에 의해 전기변색 물질의 색상이 변화하여 소자의 광투과 특성이 변하게 된다.The electrochromic device is generally composed of a cathode, an anode, an electrolyte, and an electrochromic material. The electrochromic material is formed in a film form on one or both electrodes, or may be included in an electrolyte. When the electric field is applied to the electrochromic device, the color of the electrochromic material is changed by the electric redox reaction, thereby changing the light transmission characteristics of the device.
상기 전기 변색 소자를 활용한 응용 제품 중 가장 성공적인 제품으로는 자동차용 백미러, 스마트윈도우가 있으며, 또는 전광판, 전자북 등의 디스플레이에 응용하기 위한 개발도 진행 중이다. 자동차용 백미러에 적용되는 예를 보면, 자동차 운행시 백미러를 통해 들어오는 강한 불빛은 운전자의 시야를 방해하여 사고의 위험을 초래할 수 있으며, 이를 방지하기 위하여 백미러의 반사율을 최적화함으로써 운전자의 눈부심을 방지하고 시야를 확보하도록 하는 기능을 전기변색소자를 통해 구현할 수 있다.The most successful products using the electrochromic device include a rear view mirror for automobiles and a smart window, or development for application to a display such as an electronic board or an electronic book. For example, when applied to a rearview mirror for automobiles, the strong light entering through the rearview mirror may interfere with the driver's vision and cause an accident, and in order to prevent the driver's glare by optimizing the reflectance of the rearview mirror The ability to secure the field of view can be realized through electrochromic devices.
본 발명은 합성이 간단하고 인가전압에 따라 미세하게 색 강도 조절이 가능하며, 비올로겐으로는 잘 알려지지 않은 녹색 계열의 색을 띄는 비올로겐 유도체를 제공하는 것을 목적으로 한다. 본 발명의 다른 목적은 이 유도체를 포함하는 전기변색 소자를 제공하는 것이다.An object of the present invention is to provide a viologen derivative that has a simple green color and can be finely adjusted according to an applied voltage, and has a green-based color, which is not well known as a viologen. Another object of the present invention is to provide an electrochromic device comprising the derivative.
본 발명의 비올로겐 유도체는 하기 화학식1로 표시된다.The viologen derivatives of the present invention are represented by the following formula (1).
상기 식에서 R1은 할로겐 원소를 포함하는 수소, 탄소수가 1~20의 알킬기 또는 알킬렌기이고, X는 비올로겐의 상대이온으로 F-, Br-, Cl-, ClO4 -, BF4 -, I-, PF6 -, SO2CF3 - 또는 (CF3SO3 -)2N 가 가능하다.Wherein R 1 is hydrogen, an alkyl group or alkylene group of a carbon number of 1 to 20 comprising a halogen element, X is a counter ion of Gen to rain F -, Br -, Cl - , ClO 4 -, BF 4 -, I -, PF 6 -, SO 2 CF 3 - or (CF 3 SO 3 -) 2 N is possible.
상기 화학식 1로 표시되는 유도체의 예로서 하기의 화합식1-1로 표시되는 화합물을 들 수 있다.Examples of the derivative represented by the formula (1) include compounds represented by the following formula (1-1).
본 발명의 상기 전기변색물질을 포함하여 구성되는 용액형 전기변색 소자를 포함한다. 본 발명의 전기변색소자는 투명이나 반사형의 기재상에 배치되며 작업 전극과 상대전극, 전해질을 포함하여, 상기의 작업전극, 상대전극, 전해질 중에 하나 이상은 본 발명의 전기변색물질을 포함한다. 이온전도성 전해질 용액은 전해질염이 용해된 용액을 사용할 수 있으며 상기의 전기변색 물질을 용해시켜 이를 주사하거나 진공진입 등의 방법으로 전기변색소자 제작에 사용한다.It includes a solution type electrochromic device comprising the electrochromic material of the present invention. The electrochromic device of the present invention is disposed on a transparent or reflective substrate and includes a working electrode, a counter electrode, and an electrolyte, and at least one of the working electrode, counter electrode, and electrolyte includes the electrochromic material of the present invention. . As the ion conductive electrolyte solution, a solution in which an electrolyte salt is dissolved may be used, and the electrochromic material is dissolved and used for the preparation of the electrochromic device by injection or vacuum injection.
이때, 전기변색 전해질 혼합용액은 상기 화학식 1로 표시되는 전기변색 화합물 0.0005~10M, 전해질염0.001~10M을 함유하여 사용할 수 있다.At this time, the electrochromic electrolyte mixed solution may be used by containing the electrochromic compound 0.0005 ~ 10M, the electrolyte salt 0.001 ~ 10M represented by the formula (1).
상기 비올로겐 유도체의 사용량이 0.0005M 미만이면 전기변색성이 보이지 않고 10M을 초과하면 용액에서 화합물이 용출되는 문제가 발생하므로 상기 범위를 유지하는 것이 바람직하다.If the amount of the viologen derivative is less than 0.0005M, the electrochromic property is not seen. If the amount of the viologen derivative is greater than 10M, the compound may be eluted from the solution.
이때, 상기 전해질염은 당 분야에서 사용되는 일반적인 것으로 특별히 한정하지는 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~ 10 M 범위로 사용되는 바, 상기 사용량이0.001 M 미만이면 전기변색성이 보이지 않고 10 M을 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, and 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 ~ 10 M, it is preferable to maintain the above range because the amount of the electrolyte salt is less than 0.001 M, the electrochromic property is not seen, and when the amount exceeds 10 M, the compound is eluted from the solution. .
상기 전기변색소자는 대면적의 정보표시장치, 소면적의 휴대폰 정보표시장치 및 태양광을 차단하는 자동차 창, 건물 창 등에 이용될 수 있다. The electrochromic device may be used for a large area information display device, a small area mobile phone information display device, a car window for blocking sunlight, a building window, and the like.
본 발명의 신규한 비올로겐 유도체는 합성이 쉽고 간단하며, 전기변색 소자에 적용되었을 때 낮은 전압에서도 녹색 계열의 색으로 구현이 가능한 전기변색 특성을 가진다.The novel viologen derivatives of the present invention are easy and simple to synthesize, and have electrochromic properties that can be implemented in green-based colors even at low voltages when applied to electrochromic devices.
이러한 전기변색물질은 전기변색 소자의 구성으로 효과적으로 이용되며, 제조된 전기변색소자는 디스플레이, 전자책, 전자종이, 자동차 후사경, 휴대용 컴퓨 터, 태양광조절창, 장식용 제품 등의 다방면에서 응용이 가능하다.The electrochromic material is effectively used as an electrochromic device, and the manufactured electrochromic device can be applied to various fields such as displays, e-books, electronic paper, automobile rearview mirrors, portable computers, solar control windows, and decorative products. Do.
이하의 실시 예를 통하여 본 발명을 구체적으로 설명하는바, 하기의 실시에는 오로지 본 발명을 구체적으로 설명하기 위한 것으로 이들 실시 예에 의해 본 발명을 한정하는 것은 아니다.Hereinafter, the present invention will be described in detail with reference to the following examples. However, the following examples are only for explaining the present invention in detail, and the present invention is not limited thereto.
[실시 예 1][Example 1]
* 화합물 1-1의 제조 * Preparation of Compound 1-1
하기 화학식 2와 같이, N,N-디메틸포름아마이드(N,N-dimethylformamide) 350ml에 2,2′비피리딜(2,2′bipyridyl) (70g, 0.44 M)을 완용시킨 후 1,2-디브로모에탄(1,2-Dibromoethane) (42.60g, 0.22 M)을 첨가하여 교반하에서 고형 침전물이 형성될 때까지 12~24시간 환류시켜 주었다. 반응 혼합물을 냉각시킨 후 침전물을 여과하여 MeOH로 수회 세척하고 재결정화하여 감압에서 건조시켜 진갈색의 고체 상태로 화합물을 얻을 수 있었다.(수율 65%)As shown in Chemical Formula 2, after completing 2,2 ′ bipyridyl (2,2 ′ bipyridyl) (70 g, 0.44 M) in 350 ml of N, N-dimethylformamide, 1,2- Dibromoethane (1,2-Dibromoethane) (42.60 g, 0.22 M) was added and refluxed for 12 to 24 hours until a solid precipitate formed under stirring. After cooling the reaction mixture, the precipitate was filtered, washed several times with MeOH, recrystallized and dried under reduced pressure to obtain a compound as a dark brown solid (yield 65%).
[실시 예 2] [Example 2]
* 화합물 1-1을 이용한 전기변색소자 제작 * Electrochromic device fabrication using compound 1-1
상기 실시예1에 의하여 얻어진 비올로겐 화합물(0.1g)을 전해질염 N-Lithiotrifluoromethane sulfonamide(0.5g)과 유기용매 Propylene Carbonate (10ml)와 혼합하여 전극인 ITO 유리 두 장 사이에 두께 100㎛의 스페이서를 두고, 주입한 후 밀봉하여 액체형 전기변색 소자를 제조하였다. 상기 제조된 전기변색 소자는 최소 1.3V 전압을 걸어줄 경우 green 색으로 변색 되었다.The viologen compound (0.1 g) obtained in Example 1 was mixed with electrolyte salt N-Lithiotrifluoromethane sulfonamide (0.5 g) and an organic solvent Propylene Carbonate (10 ml) to form a spacer having a thickness of 100 μm between two sheets of ITO glass as an electrode. After the injection, and sealed to prepare a liquid electrochromic device. The manufactured electrochromic device was changed to green color when a minimum voltage of 1.3V was applied.
도 1-a는 실시예2에 의하여 제조된 전기변색 소자의 구동전압을 측정하여 나타낸 그래프이고,1-a is a graph showing the measurement of the driving voltage of the electrochromic device manufactured in Example 2,
도 1-b 는 실시예 2에 의해 제조된 전기변색 소자의 구동전압에 따른 흡광도 변화를 측정하여 나타낸 그래프이다.1-b is a graph showing the measured absorbance change according to the driving voltage of the electrochromic device manufactured in Example 2. FIG.
도 2 는 실시 예 2 에 의하여 제조된 전기변색 소자의 소색/착색 상태의 사진이다.FIG. 2 is a photograph of a discolored / colored state of the electrochromic device manufactured according to Example 2. FIG.
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| US20020114056A1 (en) | 1999-02-18 | 2002-08-22 | Horst Berneth | Electrochromic device having improved light stability |
| US20020145790A1 (en) | 1997-08-18 | 2002-10-10 | Horst Berneth | UV-protected electrochromic solution |
| US20030129368A1 (en) | 2001-10-26 | 2003-07-10 | Horst Berneth | Electrochromic device and novel electrochromic compounds |
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| US20020145790A1 (en) | 1997-08-18 | 2002-10-10 | Horst Berneth | UV-protected electrochromic solution |
| US20020114056A1 (en) | 1999-02-18 | 2002-08-22 | Horst Berneth | Electrochromic device having improved light stability |
| US20030129368A1 (en) | 2001-10-26 | 2003-07-10 | Horst Berneth | Electrochromic device and novel electrochromic compounds |
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