KR20060062151A - Synthesis of new conductive polymer - Google Patents
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Abstract
본 발명은 전자 재료로 사용가능한 하기 화학식으로 나타낸 새로운 전도성 고분자인 플로렌 공중합체와 그 제조 방법에 관한 것이다.The present invention relates to a florene copolymer which is a novel conductive polymer represented by the following chemical formula usable as an electronic material, and a method for producing the same.
플로렌, 공중합체, 전도성 고분자 Florene, Copolymer, Conductive Polymer
Description
도면1은 본 발명의 실시예 2 의 중합체에 대한 광 흡수 및 광 발광스펙트럼을 나타냈다.Figure 1 shows the light absorption and photoluminescence spectrum for the polymer of Example 2 of the present invention.
본 발명은 전자 소재로 사용할 수 있는 새로운 플로렌계 전도성 고분자에 관한 것으로 화학식1의 구조를 가진다. 본 발명에서 합성한 물질은 고분자 전지 및 전자차폐제 등에도 이용이 가능할 뿐만 아니라, 특히 유기 전계발광 소자에 청색 발광 재료로써 높은 성능이 기대된다. The present invention relates to a novel florenic conductive polymer that can be used as an electronic material and has a structure of Formula 1. The materials synthesized in the present invention can be used not only for polymer batteries and electron shielding agents, but also for high performance as blue light emitting materials, especially for organic electroluminescent devices.
전자 소재 특히 재료에 대한 연구는 많은 과학자에 의해 진행되어 많은 성과를 이루어 왔지만 현재까지도 소자의 발달에 비해 소재의 발달은 매우 느리다 할 수 있다. 특히, 유기전계발광 재료는 아직까지도 충분한 성능을 갖고 있는 재료가 개발되어 있지 못하다. 현재 사용되고 있는 유기전계발광 소자용 발광 재료로는 크게 저분자 재료와 고분자 재료로 구분할 수 있다. 고분자 재료는 저분자 재료에 비해 열적 안정성이 뛰어나고 수분이나 산소에 의해 쉽게 파괴되지 않는 등 많은 장점을 갖고 있다. 그러나 현재까지는 충분한 성능을 보유한 고분자 발광 재료가 개발되지 못한 실정이다. 특히 지금까지 알려진 청색 발광 재료는 유기용매에 대한 용해도, 양자효율, 열적 안정성, 색순도 문제 등 재료 자체에 상당한 문제점을 갖고 있다. 이에 본 발명에서는 유기 용매에 잘 녹고 열적 안정성이 뛰어나고 넓은 밴드갭을 갖고 있어서 청색 발광이 가능한 재료로 플로렌계 공중합체를 개발하였다. Although research on electronic materials, especially materials, has been carried out by many scientists, the development of materials is very slow compared to the development of devices. In particular, the organic electroluminescent material has not been developed a material that still has sufficient performance. The light emitting materials for organic electroluminescent devices currently used can be largely classified into low molecular materials and high molecular materials. Polymer materials have many advantages, such as excellent thermal stability and are not easily destroyed by moisture or oxygen compared to low molecular materials. However, until now, the polymer luminescent material having sufficient performance has not been developed. In particular, the blue light emitting materials known so far have significant problems in the material itself, such as solubility in organic solvents, quantum efficiency, thermal stability, and color purity. Therefore, in the present invention, a fluorine-based copolymer was developed as a material that is well soluble in an organic solvent, has excellent thermal stability, and has a wide bandgap, and capable of emitting blue light.
플로렌 단량체와 중합체에 대한 물질 및 제조 기술은 이미 다우 케미칼등에서 특허를 보유하고 있다. 그러나 본 발명에서 제안한 화학식을 갖는 물질은 어느 누구도 제안한 적이 없는 새로운 형태의 전도성 고분자이다. Materials and manufacturing techniques for florene monomers and polymers are already patented by Dow Chemical et al. However, the material having the chemical formula proposed in the present invention is a new type of conductive polymer that no one has proposed.
본 발명에서의 기술적 과제는 제조방법이 간단하면서도 유기 용매에 잘 녹고 열적 안정성이 뛰어나고 넓은 밴드갭을 갖고 있어서 청색 발광이 가능하므로 유기전계발광 소자에 발광재료로 사용가능할 뿐만 아니라, 고분자 전지, 전자차폐제로도 이용 가능한 새로운 플로렌계 전도성 고분자를 제공하는 것이다.
The technical problem in the present invention is not only can be used as a light emitting material in the organic electroluminescent device because the manufacturing method is simple, well soluble in organic solvents, excellent thermal stability and has a wide bandgap, and can be used as a light emitting material in an organic electroluminescent device, It is to provide a new floren-based conductive polymer that can also be used.
본 발명은 화학식1에 나타낸 새로운 전도성 고분자를 합성하는 것을 특징으로 하고 있다. The present invention is characterized by synthesizing a new conductive polymer represented by the formula (1).
화학식1 Formula 1
여기서 R1은 알킬기(부틸기,헥실기,옥틸기등 탄소수 1∼ 22개), R2는 페닐기, 알킬기 또는 수소, R3는 페닐기, 알킬기 또는 안트라센등 이고, R4와 R5는 수소 또는 알킬기(부틸기,헥실기,옥틸기등 탄소수 1∼10개) 나타내고 n과 m은 1 이상의 정수를 나타낸다.Wherein R 1 is an alkyl group (1-22 carbon atoms such as butyl group, hexyl group, octyl group), R 2 is phenyl group, alkyl group or hydrogen, R 3 is phenyl group, alkyl group or anthracene, and R 4 and R 5 are hydrogen or An alkyl group (1-10 carbon atoms, such as a butyl group, a hexyl group, an octyl group) is shown, n and m represent an integer of 1 or more.
이하, 본 발명을 보다 상세하게 설명하면 다음과 같다. Hereinafter, the present invention will be described in more detail.
먼저 단량체인 2,7-디브로모-9,9'-디알킬닐플로렌(3) 및 1,3-비스(파라-브로모페닐)이미다졸-2-일리덴(4) 합성이다. 반응식은 아래와 같다.First is the synthesis of the monomers 2,7-dibromo-9,9'-dialkylylfluorene (3) and 1,3-bis (para-bromophenyl) imidazole-2-ylidene (4). The scheme is shown below.
반응식1Scheme 1
전구체인 2,7-디브로모 9,9-디알킬플로렌은 이미 알려진 물질로서 기존 제조법을 이용해 제조하였고, 1,3-비스(파라-브로모페닐)이미다졸-2-일리덴(4)는 브로모아닐린, 파라포름알데히드, 염산 그리고 글리옥살 수용액을 반응시켜 제조할 수 있었다. 위에서 만들어진 단량체 2,7-디브로모 9,9-디알킬플로렌(3)과 1,3-비스(파라-브로모페닐)이미다졸-2-일리덴(4)을 니켈 촉매 하에서 공중합을 시켜 새로운 플로렌계 전도성 고분자를 얻을 수 있다. 과정은 반응식2에 나타내었다. Precursor 2,7-dibromo 9,9-dialkylfluorene is a known material and prepared using conventional methods, 1,3-bis (para-bromophenyl) imidazol-2-ylidene (4 ) Can be prepared by reacting bromoaniline, paraformaldehyde, hydrochloric acid and glyoxal aqueous solution. Copolymerization of the monomer 2,7-dibromo 9,9-dialkylfluorene (3) and 1,3-bis (para-bromophenyl) imidazole-2-ylidene (4) made above under a nickel catalyst was carried out. To obtain a new florenic conductive polymer. The procedure is shown in Scheme 2.
반응식2Scheme 2
상기 반응식2에서 R1은 알킬기(부틸기,헥실기,옥틸기,등 탄소수가1~22개)등이다. 이하, 실시예를 참조로 본 발명을 더욱 상세히 설명한다. 그러나 본 발명의 범위와 정신은 특허청구범위로부터 벗어나지 않는 한 이들 실시예 범위로 한정되는 것은 아니다.R 1 in Scheme 2 is an alkyl group (butyl group, hexyl group, octyl group, etc., 1 to 22 carbon atoms). Hereinafter, the present invention will be described in more detail with reference to Examples. However, the scope and spirit of the present invention is not limited to the scope of these embodiments without departing from the claims.
실시예 1Example 1
1,3-비스(파라-브로모페닐)이미다졸-2-일리덴(4)의 합성 Synthesis of 1,3-bis (para-bromophenyl) imidazol-2-ylidene (4)
온도계와 온도 조절 센서 및 환류 콘덴스가 부착된 100밀리리터 3구 플라스크에 톨루엔 15 밀리리터 그리고 파라포름알데히드 0.755그램을 넣고 교반한다. 4-브로모아닐린 8.6그램을 10밀리리터 톨루엔에 녹인 용액을 파라포름알데히드가 들어있는 반응용기에 교반하면서 서서히 적하시킨 후 온도를 100도 까지 올려 고체를 모두 녹인다. 그리고 반응 혼합물을 40도 까지 냉각시킨 후 6노르말 염산 수용액 4.15밀리리터를 서서히 첨가한고 5분간 교반 시킨다. 5분 후 40퍼센트의 글리옥살 수용액 3.63그램을 반응용액에 첨가 한 후 다시 5분간 실온에서 교반시킨다. 그리고 온도를 100도로 올려 2시간 동안 환류 시킨다. 반응 혼합물이 가열되는 동안 흑색 고체가 생성되면 가열을 멈추고 실온으로 냉각시킨 후 진공으로 휘발성 물질을 제거하고 아세토니트릴로 씻고 필터하여 갈색 고체를 얻었다. 그리고 여러 종류의 유기 용매로 씻은 후 이를 70도의 진공 오븐에서 충분히 건조시킨 후 무게를 측정한 결과 수득율은 70% 얻었다. 구조는 NMR 및 질량분석계등을 이용하여 확인하였다. 1H-NMR (CDCl3) δ 7.48(4H,d,Ar), 7.71(4H,d,Ar), 8.24(2H,d), 10.1(1H,t) ; 13C-NMR(CDCl3) δ 120∼137 (8개의 피크) ; GC/MS, m/e 481(M+)In a 100 milliliter three-necked flask with thermometer, temperature control sensor and reflux condensate, add 15 milliliters of toluene and 0.755 grams of paraformaldehyde and stir. A solution of 8.6 grams of 4-bromoaniline in 10 milliliter toluene was slowly added dropwise to a reaction vessel containing paraformaldehyde while stirring to raise the temperature to 100 degrees to dissolve all solids. After cooling the reaction mixture to 40 degrees, 4.15 milliliters of 6-normal hydrochloric acid aqueous solution was slowly added and stirred for 5 minutes. After 5 minutes, 3.63 g of 40% aqueous glyoxal solution was added to the reaction solution, which was then stirred for 5 minutes at room temperature. The temperature is raised to 100 degrees and refluxed for 2 hours. If a black solid formed while the reaction mixture was heated, the heating was stopped, cooled to room temperature, the volatiles were removed in vacuo, washed with acetonitrile and filtered to give a brown solid. After washing with various organic solvents, the resultant was dried in a vacuum oven at 70 degrees and then weighed to obtain 70% yield. The structure was confirmed using NMR and mass spectrometer. 1 H-NMR (CDCl 3 ) δ 7.48 (4H, d, Ar), 7.71 (4H, d, Ar), 8.24 (2H, d), 10.1 (1H, t); 13 C-NMR (CDCl 3 ) δ 120 to 137 (8 peaks); GC / MS, m / e 481 (M + )
실시예 2Example 2
1,3-비스(파라-브로모페닐)이미다졸-2-일리덴과 2,7-디브로모-9,9'-디헥실플로렌의 공중합(5)Copolymerization of 1,3-bis (para-bromophenyl) imidazol-2-ylidene with 2,7-dibromo-9,9'-dihexylflorene (5)
질소 분위기 하에서 교반기가 있는 100밀리리터들이 3구 플라스크에 0.13그램(1밀리몰) 니켈클로라이드와 3.02그램(31밀리몰)의 아연, 2.0그램(7.6밀리몰)의 트리페닐포스핀, 0.156그램(1밀리몰)의 2,2-디피리딜을 넣고 40℃로 가열 후 DMF용매 넣고 90℃로 온도를 올려 활성화시킨 뒤 용액이 적갈색을 띠면 2,7-디브로모-9,9'-디헥실플로렌 2.2그램(4.5밀리몰)과 1,3-비스(파라-브로모페닐)이미다졸-2-일리덴 0.21그램(0.5밀리몰)을 DMF 10밀리리터에 녹여 넣고 80℃로 72시간동안 교반시킨다. 말단기로 9-브로모안트라센 0.25그램(1밀리몰)넣고 6시간 반응시킨다. 반응이 완결되면 반응물을 증류수와 염산혼합물에 넣고 3시간 교반 후 거르고 건조시킨다. 메틸렌클로라이드로 녹여 거른 후 용매를 완전히 날려 옅은 갈색 고체를 얻었다. 구조는 NMR등을 이용하여 확인하였다. 중량평균분자량(Mw)는 10,187, 수평균분자량(Mn)는 5232로서 Mw/Mn(PID)는 1.94이다. 또한 유리전이온도(Tg)는 113.95℃이고 초기열분해온도는 439℃로 열적으로 매우 안정한 물질로 확인되었다.In a 100 milliliter three-neck flask with agitator under a nitrogen atmosphere, 0.13 grams (1 mmol) nickel chloride and 3.02 grams (31 mmol) zinc, 2.0 grams (7.6 mmol) triphenylphosphine, 0.156 grams (1 mmol) Add 2,2-dipyridyl, heat it to 40 ℃, add DMF solvent, raise the temperature to 90 ℃, activate it, and when the solution is reddish brown, 2.2 grams of 2,7-dibromo-9,9'-dihexylfluorene ( 4.5 mmol) and 0.21 gram (0.5 mmol) of 1,3-bis (para-bromophenyl) imidazole-2-ylidene are dissolved in 10 milliliters of DMF and stirred at 80 ° C. for 72 hours. 0.25 g (1 mmol) of 9-bromoanthracene as a terminal group was added and reacted for 6 hours. After the reaction was completed, the reaction mixture was added to distilled water and hydrochloric acid mixture, stirred for 3 hours, filtered, and dried. After dissolving and filtering with methylene chloride, the solvent was completely blown to obtain a pale brown solid. The structure was confirmed using NMR. The weight average molecular weight (M w ) is 10,187, the number average molecular weight (M n ) is 5232 and M w / M n (PID) is 1.94. In addition, the glass transition temperature (Tg) was 113.95 ℃ and the initial pyrolysis temperature was 439 ℃ was confirmed as a very thermally stable material.
도면1에는 생성물인 1,3-비스(파라-브로모페닐)이미다졸-2-일리덴과 2,7-디브로모-9,9'-디헥실플로렌의 공중합체 광흡수스펙트럼 및 광발광 스펙트럼을 나타내었다. 1,3-비스(파라-브로모페닐)이미다졸-2-일리덴과 2,7-디브로모-9,9'-디헥실플로렌의 공중합체는 360 나노미터에서 최대 흡수파장을 나타냈으며 414 나노미터에서 최대 발광파장을 나타낸 것으로 넓은 밴드갭을 갖는 완전한 청색발광체임을 알 수 있다. Figure 1 shows a light absorption spectrum and photoluminescence copolymer of 1,3-bis (para-bromophenyl) imidazole-2-ylidene and 2,7-dibromo-9,9'-dihexylfluorene as a product. The spectrum is shown. The copolymer of 1,3-bis (para-bromophenyl) imidazol-2-ylidene and 2,7-dibromo-9,9'-dihexylflorene showed a maximum absorption wavelength at 360 nanometers. The maximum light emission wavelength at 414 nanometers indicates that it is a complete blue light emitter with a wide bandgap.
본 발명에서 제조한 중합체는 고분자 전지 및 전자차폐제등에도 이용이 가능할 뿐만 아니라. 많은 전자 소재로 이용이 가능하다. 특히 유기 전계발광 소자에 청색 발광 재료로써 사용될 수 있다.
The polymer prepared in the present invention can be used not only in polymer batteries and electron shielding agents. Many electronic materials are available. In particular, it can be used as a blue light emitting material in an organic electroluminescent element.
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