KR100422109B1 - Polymer coordination complex useful as an electrode - Google Patents
Polymer coordination complex useful as an electrode Download PDFInfo
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- KR100422109B1 KR100422109B1 KR10-2001-0026324A KR20010026324A KR100422109B1 KR 100422109 B1 KR100422109 B1 KR 100422109B1 KR 20010026324 A KR20010026324 A KR 20010026324A KR 100422109 B1 KR100422109 B1 KR 100422109B1
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Abstract
본 발명은 전극으로 유용한 고분자 배위화합물에 관한 것으로, PEDOT(폴리(3,4-에틸렌 디옥시티오펜))-PSS(폴리(4-스티렌설포네이트))와 배위수를 갖는 금속 이온이 배위결합된 본 발명에 따른 고분자 배위화합물은 개선된 전기적 물성을 가져 전기소자의 전극 또는 정공주입층에 유용하게 사용된다.BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a polymer coordination compound useful as an electrode, wherein PEDOT (poly (3,4-ethylene dioxythiophene))-PSS (poly (4-styrenesulfonate)) and a metal ion having a coordination number are coordinated. The polymer coordination compound according to the present invention has improved electrical properties and is usefully used for electrodes or hole injection layers of electric devices.
Description
본 발명은 전극으로 유용한 고분자 배위화합물에 관한 것으로, 구체적으로는 비공유 전자쌍을 갖는 고분자 화합물과 배위수를 갖는 금속 이온이 배위결합되어 개선된 전기적 특성을 갖는, 전극으로 유용한 고분자 배위화합물에 관한 것이다.The present invention relates to a polymer coordination compound useful as an electrode, and more particularly, to a polymer coordination compound useful as an electrode having coordination bonds between a polymer compound having a lone pair and a metal ion having a coordination number.
바이에르 아크티엔 게젤샤프트(Bayer AG) 사에서 제조되어 베이트론-피(Baytron-P)라는 제품명으로 시판되고 있는 PEDOT(폴리(3,4-에틸렌 디옥시티오펜))-PSS(폴리(4-스티렌설포네이트)) 수용액은, ITO(인듐주석산화물) 전극 위에 스핀코팅하여 정공주입층을 형성하려는 목적으로 유기발광소자의 제작시 널리이용되고 있으며, 정공주입물질인 이 PEDOT-PSS는 하기 화학식 1의 구조를 갖는다:PEDOT (poly (3,4-ethylenedioxythiophene))-PSS (poly (4-styrene) manufactured by Bayer AG Tiershaft (Bayer AG) and sold under the trade name Baytron-P Sulfonate)) aqueous solution is widely used during the fabrication of an organic light emitting device for the purpose of forming a hole injection layer by spin coating on an ITO (indium tin oxide) electrode, this PEDOT-PSS is a hole injection material Has the structure:
이제까지, 유기발광소자에서는 PEDOT-PSS 수용액을 어떠한 첨가물 없이 원액 그대로 스핀코팅하여 사용해 왔으며, 단지 증류수의 첨가를 통해 용액의 농도를 변화시켜 정공주입층의 두께를 적절히 조절해 왔다.Until now, the organic light emitting device has been used by spin-coating the PEDOT-PSS aqueous solution as it is without any additives, it has been appropriately adjusted the thickness of the hole injection layer by changing the concentration of the solution through the addition of distilled water.
한편, 에스. 고쉬(S. Ghosh)는 PEDOT-PSS 용액에 MgSO4또는 CaSO4와 같은 물질 첨가시 PEDOT와 금속 이온 간에 이온 결합(ionic bond)이 형성됨을 설명하고, 이를 축전지의 전극에 도입한 바 있다(문헌[S. Ghosh, J. R. Rasmusson and O. Inganas, Adv. Mater., 10(14), 1097(1998); 및 S. Ghosh and O. Inganas, Adv. Mater., 11(14), 1214(1999)] 참조).Meanwhile, S. S. Ghosh has described the formation of ionic bonds between PEDOT and metal ions when a substance such as MgSO 4 or CaSO 4 is added to a PEDOT-PSS solution and introduced it into the electrode of a battery. S. Ghosh, JR Rasmusson and O. Inganas, Adv. Mater., 10 (14), 1097 (1998); and S. Ghosh and O. Inganas, Adv. Mater., 11 (14), 1214 (1999). ] Reference).
그러나, 상기 PEDOT-PSS 화합물은 그 자체 또는 이온결합된 형태로 소자에 적용될 때 발광효율의 향상 및 수명의 연장에 한계를 가지고 있었다.However, the PEDOT-PSS compound has a limitation in improving the luminous efficiency and extending the life when applied to the device in itself or in an ion-bonded form.
이에 본 발명자들은 지속적으로 연구한 결과 비공유 전자쌍을 갖는 고분자 PEDOT-PSS가 배위수를 갖는 금속 이온과 배위결합(coordination bond)하여 개선된전기적 특성을 갖는 고분자 배위화합물을 형성함을 발견하고 본 발명을 완성하게 되었다.Accordingly, the present inventors found that the polymer PEDOT-PSS having a non-covalent electron pair coordination bond with a metal ion having a coordination number to form a polymer coordination compound having improved electrical properties. It was completed.
본 발명은 개선된 전기적 특성을 가져 전극으로 유용한 고분자 배위화합물을 제공하는 것을 목적으로 한다.It is an object of the present invention to provide a polymeric coordination compound useful as an electrode with improved electrical properties.
도 1은 실시예 1에서 제조된 반응혼합액들의 전도도 측정 결과이고,1 is a result of measuring the conductivity of the reaction mixtures prepared in Example 1,
도 2 및 3은 각각 실시예 2에서 제조된 소자들의 전압에 따른 전류의 변화 및 전류에 따른 휘도의 변화 그래프이다.2 and 3 are graphs showing a change in current and a change in luminance according to voltage of the devices manufactured in Example 2, respectively.
상기 목적을 달성하기 위하여 본 발명에서는, PEDOT(폴리(3,4-에틸렌 디옥시티오펜))-PSS(폴리(4-스티렌설포네이트))와 배위수를 갖는 금속 이온이 배위결합된 고분자 배위화합물을 제공한다.In order to achieve the above object, in the present invention, PEDOT (poly (3,4-ethylene dioxythiophene))-PSS (poly (4-styrenesulfonate)) and the polymer coordination compound of the coordination number of metal ions having a coordination number To provide.
이하 본 발명에 대하여 상세히 설명한다.Hereinafter, the present invention will be described in detail.
본 발명에서는, PEDOT-PSS와 배위수를 갖는 금속의 염을 반응 매질 중에서 상온에서 반응시킴으로써 본 발명에 따른 고분자 배위화합물을 형성할 수 있다.In the present invention, the polymer coordination compound according to the present invention can be formed by reacting PEDOT-PSS with a salt of a metal having a coordination number at room temperature in a reaction medium.
본 발명의 고분자 배위화합물 형성에 사용될 수 있는 상기 염은 MaNb로 나타내어지는데, M은 4 이상, 바람직하게는 4 내지 6의 배위수를 갖는 전이 금속 이온일 수 있고, 그의 구체적인 예로는 Cu2+, Ni2+, Zn2+, Co2+, Fe2+, Fe3+, Mn2+, Mn7+, Cr3+및 Cr6+를 들 수 있으며, N은 M과 염을 형성하는 음이온으로, 구체적인 예로는SO4 -, Cl-, OH-, HSO4 -, HCO3 -, O2 -, CN-, NO3 -, NO2 -, SO3 2-, CO3 2-, PO4 3-, HPO4 2-, H2PO4 -, ClO4 -, ClO3 -, ClO2 -, ClO-, CrO4 2-및 Cr2O7 2-을 들 수 있으며, a 및 b는 각각 1 내지 10의 자연수이다.The salt that can be used to form the polymer coordination compound of the present invention is represented by M a N b , M may be a transition metal ion having a coordination number of 4 or more, preferably 4 to 6, specific examples thereof are Cu 2+ , Ni 2+ , Zn 2+ , Co 2+ , Fe 2+ , Fe 3+ , Mn 2+ , Mn 7+ , Cr 3+ and Cr 6+ , where N forms a salt with M as an anion, and specific examples of the SO 4 -, Cl -, OH -, HSO 4 -, HCO 3 -, O 2 -, CN -, NO 3 -, NO 2 -, SO 3 2-, CO 3 2-, PO 4 3-, HPO 4 2-, H 2 PO 4 -, ClO 4 -, ClO 3 -, ClO 2 -, ClO -, CrO 4 2- , and Cr may be mentioned 2 O 7 2-, a and b Are natural numbers of 1 to 10, respectively.
상기 반응시 사용되는 반응 매질로는 물, 아세톤, 이소프로판올, 메탄올 및 에탄올 등을 들 수 있으며, 각 반응 물질은 매질 중의 0.001 내지 0.5M의 농도로 제조하여 사용하는 것이 바람직하다. 또한, PEDOT-PSS와 상기 염의 혼합비율은 특별히 제한되지 않고 고분자 배위화합물을 형성할 수 있는 범위이면 모두 가능하다.Examples of the reaction medium used in the reaction include water, acetone, isopropanol, methanol, ethanol, and the like, and each reaction material is preferably used at a concentration of 0.001 to 0.5 M in the medium. In addition, the mixing ratio of PEDOT-PSS and the salt is not particularly limited and may be any range as long as it can form a polymer coordination compound.
본 발명에 따르면, PEDOT-PSS 고분자가 가지는 비공유 전자쌍들이 금속 이온의 빈 자리에 들어가 옥텟 규칙을 만족하며 금속 이온들과 착체를 형성함으로써 서로 떨어져 있는 PEDOT-PSS 고분자들이 가교(crosslinking)되어 고분자 네트워크 구조를 만든다. 이 네트워크 구조를 통한 전자의 이동은 고분자와 고분자 사이를 움직이는 전자의 이동경로를 짧게 하므로 전기적 특성의 향상을 가져온다.According to the present invention, the PEDOT-PSS polymers which are separated from each other by crosslinking the PEDOT-PSS polymers which are separated from each other by entering the empty sites of the metal ions, satisfying the octet rule and forming a complex with the metal ions are formed. Make The movement of electrons through this network structure shortens the movement path of the electrons moving between the polymer and the polymer, thereby improving the electrical properties.
이와 같이, 본 발명에 따른 고분자 배위화합물은 그 네트워크 구조에 기인하여 개선된 전기적 물성을 가지므로, 이 배위화합물로 이루어진 층(박막 및 후막)은 전기소자의 전극 또는 정공주입층으로서 사용되어 소자의 휘도 및 발광효율을 향상시키고 수명을 증가시킬 수 있다.As described above, since the polymer coordination compound according to the present invention has improved electrical properties due to its network structure, the layer (thin film and thick film) composed of this coordination compound is used as an electrode or a hole injection layer of an electric device to It is possible to improve the brightness and luminous efficiency and to increase the lifetime.
이하 실시예를 통하여 본 발명을 더욱 상세히 설명한다. 단 본 발명의 범위가 하기 실시예만으로 한정되는 것은 아니다.The present invention will be described in more detail with reference to the following examples. However, the scope of the present invention is not limited only to the following examples.
실시예 1Example 1
물 69 ml에 0.75%의 PEDOT-PSS 수용액 1 ml와 CuSO4수용액 1 ml를 첨가하고, 혼합액을 상온에서 충분히 반응시켰다. 이때, CuSO4수용액의 농도를 0, 0.01, 0.02, 0.03, 0.04, 0.05, 0.06, 0.07, 0.08, 0.09, 0.1, 0.2, 0.3, 0.4 및 0.5M로 변화시켰다. 얻어진 반응혼합액 각각의 전도도(mScm-1)를 측정하여 도 1에 나타내었다.1 ml of 0.75% PEDOT-PSS aqueous solution and 1 ml CuSO 4 aqueous solution were added to 69 ml of water, and the mixed solution was sufficiently reacted at room temperature. At this time, the concentration of the CuSO 4 aqueous solution was changed to 0, 0.01, 0.02, 0.03, 0.04, 0.05, 0.06, 0.07, 0.08, 0.09, 0.1, 0.2, 0.3, 0.4 and 0.5M. The conductivity (mScm −1 ) of each obtained reaction mixture was measured and shown in FIG. 1.
도 1의 결과로부터, PEDOT-PSS와 CuSO4간에 고분자 배위화합물이 형성되었고, 이 배위화합물이 우수한 전도도를 가짐을 알 수 있다.From the results of FIG. 1, it was found that a polymer coordination compound was formed between PEDOT-PSS and CuSO 4 , and this coordination compound has excellent conductivity.
실시예 2Example 2
상기 실시예 1과 동일한 방법으로 반응혼합액을 제조하되, CuSO4수용액의 농도를 0, 0.001, 0.01, 0.05, 0.1 및 0.5M로 변화시켰다. 반응 완료 후 0.45㎛의 필터를 사용하여 침전물을 제거하였다. 얻어진 여액을 ITO 위에 스핀코팅한 후 핫 플레이트(hot plate) 위에서 어닐링(annealing)하여 용매를 제거함으로써 두께 50 nm의 고분자 박막(정공주입층)을 형성하였다. 그 위에, N,N'-디페닐-N,N'-비스(3-메틸페닐)-1,1'-디페닐-4,4'-디아민(TPD), 4,4'-비스(2-(9-에틸카바졸릴)-에텐-1-일)-비페닐(BCzVBi) 및 Ca를 순차적으로 진공증착시켜 각각 두께 50 nm의 정공수송층, 두께 60 nm의 발광층 및 두께 100 nm의 음극 전극층을 형성하여 유기발광소자를 제작하였다. 제조된 소자 각각의 전압(V)에 따른 전류(mA)의 변화, 및 전류에 따른 휘도(a.u.)의 변화를 측정하여 도 2 및 3에 나타내었다.A reaction mixture was prepared in the same manner as in Example 1, but the concentration of the CuSO 4 aqueous solution was changed to 0, 0.001, 0.01, 0.05, 0.1, and 0.5M. After completion of the reaction, the precipitate was removed using a filter of 0.45㎛. The obtained filtrate was spin coated on ITO and then annealed on a hot plate to remove the solvent to form a polymer thin film (hole injection layer) having a thickness of 50 nm. On it, N, N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'-diphenyl-4,4'-diamine (TPD), 4,4'-bis (2- (9-ethylcarbazolyl) -ethen-1-yl) -biphenyl (BCzVBi) and Ca were sequentially vacuum deposited to form a hole transport layer having a thickness of 50 nm, a light emitting layer having a thickness of 60 nm, and a cathode electrode layer having a thickness of 100 nm, respectively. To an organic light emitting device. 2 and 3 show changes in current mA according to voltage V and changes in luminance au according to current.
도 2 및 3의 결과로부터, PEDOT-PSS 박막을 포함하는 소자에 비해, 본 발명에 따른 PEDOT-PSS와 CuSO4의 배위화합물로 이루어진 박막을 포함하는 소자가 높은 전류값과 휘도값을 나타냄을 알 수 있다.From the results of FIGS. 2 and 3, it can be seen that the device including the thin film made of the coordination compound of PEDOT-PSS and CuSO 4 according to the present invention exhibits a high current value and a luminance value, compared to the device including the PEDOT-PSS thin film. Can be.
별도로, 정공주입층 형성에 CuSO4로 처리되지 않은 PEDOT-PSS만을 사용하거나, CuSO4수용액 대신에 0.05M MgSO4수용액으로 처리하여 제조한, 이온결합된 PEDOT-PSS/MgSO4를 사용하여 상기와 같은 공정으로 유기발광소자를 제작하였다. 이 소자들과 0.05M CuSO4수용액을 사용하여 제조한 소자 각각에 대해, 휘도 100 cd/m2에서의 발광효율(lm/W) 및 초기 휘도 1000 cd/m2에서의 수명(시간)을 측정하여, 그 결과를 하기 표 1에 나타내었다.Separately, using PEDOT-PSS not treated with CuSO 4 alone or ion-bonded PEDOT-PSS / MgSO 4 prepared by treating with 0.05M MgSO 4 aqueous solution instead of CuSO 4 aqueous solution to form a hole injection layer. An organic light emitting device was manufactured in the same process. For each of the devices prepared using these devices with 0.05M aqueous solution of CuSO 4, measuring the lifetime (time) in the light emission efficiency at a luminance of 100 cd / m 2 (lm / W) and an initial luminance of 1000 cd / m 2 The results are shown in Table 1 below.
상기 표 1로부터, 본 발명에 따른 PEDOT-PSS와 CuSO4의 배위화합물을 정공주입층에 이용한 유기발광소자가 금속 화합물과 전혀 결합되어 있지 않거나 또는 금속과 이온결합되어 있는 화합물을 이용한 소자에 비해 발광효율 및 수명이 훨씬 우수함을 알 수 있다.From Table 1, the organic light emitting device using the coordination compound of PEDOT-PSS and CuSO 4 in the hole injection layer according to the present invention emits light as compared to a device using a compound which is not bonded to a metal compound or is ion-bonded with a metal. It can be seen that the efficiency and lifetime are much better.
본 발명에 따른 고분자 배위화합물은 그 네트워크 구조에 기인한 개선된 전기적 물성을 가져 이 화합물로 이루어진 층은 전기소자의 전극 또는 정공주입층으로서 사용되어 소자의 휘도 및 발광효율을 향상시키고 수명을 증가시킬 수 있다.The polymer coordination compound according to the present invention has improved electrical properties due to its network structure, and the layer made of this compound can be used as an electrode or hole injection layer of an electric device to improve the brightness and luminous efficiency of the device and to increase its lifetime. Can be.
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| KR101516474B1 (en) * | 2013-05-07 | 2015-05-20 | 국립대학법인 울산과학기술대학교 산학협력단 | Plasmonic organic optoelectronic devices comprising conducting polymer electrode incoporated with silver nanoparticles |
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| WO2001020691A1 (en) * | 1999-09-10 | 2001-03-22 | Koninklijke Philips Electronics N.V. | Conductive structure based on poly-3,4-alkenedioxythiophene (pedot) and polystyrenesulfonic acid (pss) |
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| WO2001020691A1 (en) * | 1999-09-10 | 2001-03-22 | Koninklijke Philips Electronics N.V. | Conductive structure based on poly-3,4-alkenedioxythiophene (pedot) and polystyrenesulfonic acid (pss) |
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