KR20090099661A - Novel electrochromic viologens derivatives and yellow electrochromic element using the same method - Google Patents

Novel electrochromic viologens derivatives and yellow electrochromic element using the same method Download PDF

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KR20090099661A
KR20090099661A KR1020080024784A KR20080024784A KR20090099661A KR 20090099661 A KR20090099661 A KR 20090099661A KR 1020080024784 A KR1020080024784 A KR 1020080024784A KR 20080024784 A KR20080024784 A KR 20080024784A KR 20090099661 A KR20090099661 A KR 20090099661A
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electrochromic
yellow
viologen
compound
electrochromic device
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양시영
김영아
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주식회사 폴리크롬
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
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    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/15—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on an electrochromic effect
    • G02F1/1514—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on an electrochromic effect characterised by the electrochromic material, e.g. by the electrodeposited material
    • G02F1/1516—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on an electrochromic effect characterised by the electrochromic material, e.g. by the electrodeposited material comprising organic material
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Abstract

An electrochromic viologen compound, and a yellow emitting electrochromic device containing the compound are provided to control the color intensity according to the applied voltage and to allow the compound to be prepared simply. An electrochromic viologen compound is represented by the formula 1, wherein R1 is hydrogen, or C1-C20 alkyl group or alkylene group containing a halogen atom; and X is an counter ion of viologen and is F^-, Br^-, Cl^-, ClO4^-, BF4^-, I^-, PF6^-, SO2CF3^- or (CF3SO3^-)2N. The color of the electrochromic device containing the compound is yellow.

Description

신규한 전기변색 비올로겐 유도체 및 이를 이용한 노란색 계열의 색상을 발현하는 전기변색 소자{Novel electrochromic viologens derivatives and yellow electrochromic element using the same method}Novel electrochromic viologens derivatives and yellow electrochromic element using the same method

본 발명은 전기변색성을 갖는 신규한 비올로겐 유도체 및 상기의 비올로겐 유도체를 적용하여 전기변색시 yellow 계열의 색상을 띄는 전기변색 소자에 관한 것이다. 본 발명의 전기변색성 비올로겐 유도체는 합성이 쉽고 간단하며 전기변색 소자화하였을 때 전압 인가 시 기존의 비올로겐 유도체보다 다양한 색상을 구현할 수 있는 장점이 있다.The present invention relates to a novel viologen derivative having electrochromic properties and an electrochromic device having a yellow-based color when electrochromic by applying the viologen derivative. The electrochromic viologen derivative of the present invention is easy and simple to synthesize, and when the electrochromic device is applied, there is an advantage in that it is possible to implement a variety of colors than conventional viologen derivatives 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, 폴 리피리딘, 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, polyquinone and the like.

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 구 현할 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 ensure visibility can be implemented with electrochromic devices.

본 발명은 합성이 간단하고 인가전압에 따라 색 강도 조절이 가능하며, 비올로겐으로는 잘 알려지지 않은 yellow 색상을 띄는 비올로겐 유도체를 제공하는 것을 목적으로 한다. 본 발명의 다른 목적이 이 비올로겐 유도체를 포함하는 전기변색 소자를 제공하는 것이다.An object of the present invention is to provide a viologen derivative having a simple yellow color and controlling color intensity according to an applied voltage and having a yellow color which is not well known as a viologen. Another object of the present invention is to provide an electrochromic device comprising the viologen derivative.

본 발명의 비올로겐 유도체는 하기 화학식1로 표시된다.The viologen derivatives of the present invention are represented by the following formula (1).

Figure 112008019479822-PAT00001
Figure 112008019479822-PAT00001

상기 식에서 R1 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.Is hydrogen comprising the formula R 1 a halogen atom, an alkyl group or an alkylene group of carbon number 1 ~ 20, 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.

화학식 1의 예로서 하기의 화합물을 들 수 있다.Examples of the formula (1) include the following compounds.

Figure 112008019479822-PAT00002
Figure 112008019479822-PAT00002

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. 상기 비올로겐 유도체의 사용량이 0.0005M 미만이면 전기변색성이 보이지 않고 10M을 초과하면 용액에서 화합물이 용출되는 문제가 발생하므로 상기 범위를 유지하는 것이 바람직하다.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). 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 전해질염 은 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 신규 비올로겐 유도체는 합성이 쉽고 간단하며, 전기변색 소자에 적용되었을 때 낮은 전압에서도 yellow 색상으로 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 realized in a yellow color even at low voltage when applied to an electrochromic device.

이러한 전기변색물질은 전기변색 소자의 구성이 용이하게 이용되며, 이로서 제조된 전기변색소자는 디스플레이, 전자책, 전자종이, 자동차 후사경, 휴대용 컴퓨터, 태양광조절창, 장식용 제품 등의 다방면에서 응용이 가능하다.Such electrochromic materials are easily used for the construction of electrochromic devices, and the electrochromic devices manufactured therefrom are widely used in various fields such as displays, e-books, electronic papers, rearview mirrors, portable computers, solar control windows, and decorative products. It is possible.

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-dimethylformamide 100ml에 2,2’-bipyridyl (10.13g, 0.064 M)을 완용시킨 후 Methyl iodide (18.41g, 0.129 M)을 첨가하여 교반하에서 고형 침전물이 형성될때까지 6시간 환류시켰다. 반응 혼합물을 냉각시킨 후 침전물을 여과하여 MeOH로 수회 세척 후 필요에 따라 재결정 과정을 거쳐 감압에서 건조시켜 노란색의 고체 상태로 화합물을 얻을 수 있었다.(수율 69%) As shown in Chemical Formula 2, 2,2'-bipyridyl (10.13 g, 0.064 M) was completed in 100 ml of N, N-dimethylformamide, followed by addition of Methyl iodide (18.41 g, 0.129 M) until a solid precipitate was formed under stirring. It was refluxed for 6 hours. After cooling the reaction mixture, the precipitate was filtered, washed several times with MeOH, and then recrystallized as needed to dry under reduced pressure to obtain a compound in a yellow solid (yield 69%).

Figure 112008019479822-PAT00003
Figure 112008019479822-PAT00003

[실시 예 2]  Example 2

* 화합물 1-1을 이용한 전기변색소자 제작 * Electrochromic device fabrication using compound 1-1

상기의 비올로겐 화합물 1-1(0.1g)에 유기용매 Propylene Carbonate (10ml)와 전해질 N-Lithiotrifluoromethane sulfonamide(0.5g)을 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 yellow 색으로 변색 되었다.An organic solvent of propylene carbonate (10 ml) and an electrolyte N-Lithiotrifluoromethane sulfonamide (0.5 g) were mixed with the viologen compound 1-1 (0.1 g), and a spacer having a thickness of 100 μm was placed between two sheets of ITO glass as an electrode. After injection, sealing was performed to produce a liquid electrochromic device. The manufactured electrochromic device was discolored yellow when applied with a minimum voltage of 1.3V.

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.

Claims (3)

다음 화학식 1로 표시되는 전기변색 비올로겐 화합물 :The electrochromic viologen compound represented by the following Chemical Formula 1:
Figure 112008019479822-PAT00004
Figure 112008019479822-PAT00004
 (상기 식에서 R1 할로겐 원소를 포함하는 수소, 탄소수가 1~20의 알킬기 또는 알킬렌기이고, X는 비올로겐의 상대이온으로 F-, Br-, Cl-, ClO4 -, BF4 -, I-, PF6 -, SO2CF3 - 또는 (CF3SO3 -)2N 를 포함한다.)(Hydrogen, an alkyl group or alkylene group of a carbon number of 1 to 20 comprising the formula R 1 a halogen atom, X is a counter ion of Gen to rain F -, Br -, Cl - , ClO 4 -, BF 4 -, I -, PF 6 - and a 2 N), SO 2 CF 3 - - or (CF 3 SO 3). 제1항 기재의 비올로겐 유도체를 포함하는 것임을 특징으로 하는 전기변색 소자.An electrochromic device comprising the viologen derivative according to claim 1. 제 2항에 있어서, 발현되는 색상은 노랑색(yellow) 계열의 색상인 것을 특징으로 하는 전기변색 소자.The electrochromic device according to claim 2, wherein the color to be expressed is a yellow-based color.
KR1020080024784A 2008-03-18 2008-03-18 Novel electrochromic viologens derivatives and yellow electrochromic element using the same method KR20090099661A (en)

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