KR20080025263A - Tetrakisphenyl compounds and organic elecroluminescence devices using the same - Google Patents
Tetrakisphenyl compounds and organic elecroluminescence devices using the same Download PDFInfo
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Abstract
Description
도1은 본 발명에 따른 유기전계발광 소자의 구조 단면도이다. 1 is a structural cross-sectional view of an organic light emitting display device according to the present invention.
본 발명은 유기전계발광 소자에 관한 것으로, 특히 유기발광층의 청색발광물질로서 테트라페닐메탄(tetraphenylmethane) 또는 테트라페닐실란(tetraphenyl silane)구조를 갖는 화합물을 포함하는 유기전계발광 소자에 관한 것이다.The present invention relates to an organic electroluminescent device, and more particularly, to an organic electroluminescent device comprising a compound having a tetraphenylmethane or tetraphenylsilane structure as a blue light emitting material of the organic light emitting layer.
최근 표시장치의 대형화에 따라 공간 점유가 적은 평면표시소자의 요구가 증대되고 있는데, 이러한 평면표시 소자 중 하나로서 최근 유기발광다이오드(organic light emitting diode:OLED)라고도 불리는 유기전계발광 소자의 기술이 빠른 속도로 발전하고 있으며, 이미 여러 시제품들이 발표된바 있다.Recently, as the size of the display device increases, the demand for a flat display device having less space is increasing. As one of the flat display devices, an organic light emitting diode (OLED), also called an organic light emitting diode (OLED), has recently been rapidly developed. It is evolving at a rate, and several prototypes have already been announced.
유기전계발광 디스플레이는 정공 주입 전극(양극)인 제 1전극(anode)과 전자 주입 전극(음극)인 제 2전극(cathode)사이에 형성된 유기발광층에 각각 전자와 정공을 주입하면 전자와 정공이 결합하여 쌍을 이루어 생성된 엑시톤(exciton)이 들뜬상태로부터 바닥상태로 떨어지면서 이들 간의 에너지 차이가 빛으로 변환되어 발광하는 소자이다.The organic light emitting display combines electrons and holes by injecting electrons and holes into an organic light emitting layer formed between a first electrode (anode), which is a hole injection electrode (anode), and a second electrode (cathode), which is an electron injection electrode (cathode), respectively. Excitons formed in pairs fall from the excited state to the ground state, and the energy difference between them is converted into light and emits light.
이러한 유기전계발광 소자는 플라즈마 디스플레이 패널(PDP)이나 무기전계발광 소자 디스플레이에 비해 낮은 전압(예,10V이하)으로 구동할 수 있다는 장점이 있어 연구가 활발하게 진행되고 있다.Such organic electroluminescent devices have an advantage that they can be driven at a lower voltage (eg, 10V or less) than plasma display panels (PDPs) or inorganic electroluminescent device displays.
그리고 유기전계발광 소자는 넓은 시야각, 고속 응답성, 고 콘트라스트(contrast)등의 뛰어난 특징을 갖고 있으므로, 그래픽 디스플레이의 픽셀(pixel), 텔레비젼 영상 디스플레이나 표면광원(surface light source)의 픽셀로서 사용될 수 있으며, 플라스틱 같이 휠 수 있는(flexible)투명 기판 위에도 소자를 형성할 수 있고, 매우 얇고 가볍게 만들 수 있으며, 색감이 좋기 때문에 차세대 평면 디스플레이(flat panel display:FDP)에 적합한 소자이다.Organic electroluminescent devices have excellent features such as wide viewing angle, high speed response and high contrast, so they can be used as pixels in graphic displays, television image displays or surface light sources. In addition, since the device can be formed on a flexible transparent substrate such as plastic, it can be made very thin and light, and the color is good, it is suitable for the next-generation flat panel display (FDP).
또한 녹색(green),청색(blue),적색(red)의 세 가지 색을 나타낼 수 있고, 이미 잘 알려진 액정표시장치(liquid crystal display:LCD)에 비해 백라이트(backlight)가 필요치 않아 전력소모가 적으며 색감이 뛰어나 차세대 풀 칼라 디스플레이(full color display)소자로 많은 사람의 관심의 대상이 되고 있다.In addition, it can display three colors of green, blue, and red, and requires less backlight than the well-known liquid crystal display (LCD), which consumes less power. In addition, it is excellent in color and is attracting many people's attention as the next generation full color display device.
일반적인 유기전계발광 소자의 제조 과정은 다음과 같다.The manufacturing process of a general organic electroluminescent device is as follows.
먼저 투명 기판 위에 양극(anode)물질을 형성한다. 여기서 양극 물질로는 흔히 ITO(Indium Tin Oxide)가 쓰인다.First, an anode material is formed on a transparent substrate. Indium tin oxide (ITO) is commonly used as a cathode material.
그리고 양극 물질 위에 정공주입층(HIL:Hole Injecting Layer)을 형성한다. 정공주입층으로는 주로, 구리 프탈로시아닌(CuPC:copper phthalocyanine)이 사용되고, 그 두께는 약 10mm 내지 30mm로 한다.A hole injection layer (HIL) is formed on the anode material. Copper phthalocyanine (CuPC: copper phthalocyanine) is mainly used as a hole injection layer, and the thickness is made into about 10 mm-30 mm.
다음으로 정공수송층(HTL:Hole Transport Layer)을 도입한다. 정공수송층은 NPD (4.4'-bis[N-(1-naphthyl)-N-phenylamino]-biphenyl)을 약30mm 내지 60mm 정도의 두께로 증착하여 형성한다.Next, a hole transport layer (HTL) is introduced. The hole transport layer is formed by depositing NPD (4.4'-bis [N- (1-naphthyl) -N-phenylamino] -biphenyl) to a thickness of about 30 mm to 60 mm.
그리고 정공수송층 위에 유기발광층(Organic Emitting Layer)을 형성한다. 이 때 유기발광층에 필요에 따라 불순물(dopant)을 첨가한다.And an organic light emitting layer (Organic Emitting Layer) is formed on the hole transport layer. At this time, a dopant is added to the organic light emitting layer as necessary.
예를 들어 녹색발광의 경우에, 유기발광층으로는 흔히 Alq3(tris(3- hydroxy-quinolate)-aluminum)을 약 30mm 내지 60mm 정도의 두께로 증착하고, 불순물로는 MQD (N-Methylquinacridone)를 많이 쓴다.For example, in the case of green light emission, Alq3 (tris (3-hydroxy-quinolate) -aluminum) is often deposited as an organic light emitting layer to a thickness of about 30 mm to 60 mm, and impurities such as MQD (N-Methylquinacridone) Write
그다음, 유기발광층 위에 전자수송층(ETL:Electron Transport Layer) 및 전자주입층(EIL:Electron Injecting Layer)을 연속적으로 형성하거나 아니면 전자주입수송층을 형성한다. 녹색 발광의 경우에, 유기발광층으로 사용한 Alq3이 뛰어난 전자수송능력을 갖기 때문에 전자주입/수송층을 쓰지 않는 경우도 많다.Subsequently, an electron transport layer (ETL) and an electron injection layer (EIL) are formed continuously on the organic light emitting layer, or an electron injection transport layer is formed. In the case of green light emission, since Alq3 used as an organic light emitting layer has excellent electron transport ability, there are many cases where an electron injection / transport layer is not used.
다음으로 전자주입층 위에 음극(cathode)을 형성하고, 마지막으로 보호막을 형성한다.Next, a cathode is formed on the electron injection layer, and finally a protective film is formed.
일반적으로 유기EL로 풀컬러(full-color)를 구현하기 위해서는 녹색(green),적색(red),청색(blue)의 3가지 빛을 내는 발광 소자를 필요로 한다.In general, in order to realize full-color with organic EL, a light emitting device that emits three colors of green, red, and blue is required.
여기서 청색은 청색 호스트(host)에 청색 불순물을 도핑하고, 전자수송층(ETL)으로 Alq3를 사용하여 구현하며, 청색 호스트의 특성에 따라 Alq3를 생략할 수도 있다.The blue may be implemented by doping blue impurities into the blue host, using Alq3 as the electron transport layer ETL, and omitting Alq3 according to the characteristics of the blue host.
적색의 경우는 상기 소자 제작 과정 중에 녹색 불순물 대신에 적색 불순물을 도핑 함으로서 적색 파장을 얻을 수 있다.In the case of red, a red wavelength may be obtained by doping red impurities instead of green impurities during the device fabrication process.
그러나 녹색 발광 소자의 경우는 소자의 안정성이 실용화 수준까지 도달한 것으로 평가되어 지고 있지만, 청색 발광 소자의 경우에는 발광색 및 소자의 안정성이 아직 실용화 수준에 못 미치고 있으며 그 발광효율도 만족할 만한 수준에 이르지 못하고 있다는 문제점이 있다.However, in the case of the green light emitting device, the stability of the device has been evaluated to the practical use level, but in the case of the blue light emitting device, the emission color and the stability of the device are still not at the practical level, and the luminous efficiency thereof is not satisfactory. There is a problem.
따라서 본 발명은 상기의 문제점을 해결하려는 목적에서 발명된 것으로, 새로운 청색 발광물질을 합성하여 소자의 안정성 및 발광효율이 우수한 유기전계발광 소자를 제공하는데 그 목적이 있다. Therefore, the present invention has been invented for the purpose of solving the above problems, and the object of the present invention is to synthesize an organic light emitting device excellent in the stability and luminous efficiency of the device by synthesizing a new blue light emitting material.
상기와 같은 목적을 달성하기 위해, 본 발명에 따르면 제1전극, 유기발광층 및 제2전극을 포함하는 유기전계발광 소자에 있어서, 유기발광층의 청색발광물질로서 하기 화학식 1의 Th 구조를 갖는 화합물을 사용한 유기전계발광 소자를 제공한다. In order to achieve the above object, according to the present invention, in the organic electroluminescent device comprising a first electrode, an organic light emitting layer and a second electrode, a compound having a Th structure of the formula (1) as a blue light emitting material of the organic light emitting layer The organic electroluminescent element used is provided.
화학식 1Formula 1
상기 화학식에서 A는 탄소 원자 또는 규소 원자이며, R은 산소 원자 또는 하기 화학식이다.In the above formula, A is a carbon atom or a silicon atom, R is an oxygen atom or the following formula.
여기서 n은 0~3인 정수이며, Ar1은방향족 치환기로 이루어진 군으로부터 선택될 수 있다.N is an integer of 0 to 3, Ar 1 may be selected from the group consisting of aromatic substituents.
또한 Ar1은 페닐기(phenyl), 나프틸기(naphthyl), 안트라세닐기(anthracenyl) 및 페난트레닐기(phenanthrenyl)로부터 선택될 수 있다.Ar 1 may also be selected from a phenyl group, a naphthyl group, anthracenyl group, and a phenanthrenyl group.
또한 유기발광체의 청색발광물질로 사용될 수 있는 상기 화합물은 하기 화학식 2로 이루어진 화합물일 수 있다.In addition, the compound that can be used as a blue light emitting material of the organic light emitting material may be a compound consisting of the formula (2).
화학식 2Formula 2
상기 화학식에서 A는 탄소 원자 또는 규소 원자이다.In the above formula, A is a carbon atom or a silicon atom.
도1은 본 발명에 의해 형성된 유기전계발광소자의 구조 단면도이다. 상기와 같은 화합물을 유기발광층의 청색발광물질로 사용한다. 상기 화학식 2의 화합물은 다음과 같은 방법으로 합성될 수 있다. 1 is a structural cross-sectional view of an organic light emitting display device formed by the present invention. The above compound is used as a blue light emitting material of the organic light emitting layer. The compound of Formula 2 may be synthesized by the following method.
(1)테트라파라벤조일페닐메탄(tetra-p-benzoylphenylmethane)의 합성(1) Synthesis of tetra-p-benzoylphenylmethane
둥근 바닥 플라스크에 테트라파라브로모페닐메탄(tetra-p-bromophenyl methane) (6.36g)을 넣고 아르곤 분위기에서 용매인 THF(300ml)를 넣어 녹인다. 온도를 영하 78도로 유지하며, 1.6몰 BuLi 용액 (300ml)을 적가한다. 같은 온도에서 30분간 교반하고, THF(100ml)에 벤즈알데히드(4.5g)를 녹인 용액을 적가한다. 같은 온도에서 30분 교반 후 상온으로 온도를 상승시킨다. 염화암모늄 포화 용액 (300ml)를 넣고 층을 분리시킨다. 유기층을 분리하여 수분을 제거하고 감압 농축한다. 잔사에 MC(300ml)를 넣고 PCC(17.25g)를 넣은 다음 12시간 교반시킨다. 반응액을 여과하여 감압 농축하고, THF/메탄올 혼합용매에서 재결정하여 표지 화합물(6g)을 얻었다. Tetra-p-bromophenyl methane (6.36 g) is added to a round bottom flask and THF (300 ml) is dissolved in an argon atmosphere. The temperature is maintained at minus 78 degrees and 1.6 molar BuLi solution (300 ml) is added dropwise. Stir at the same temperature for 30 minutes and add dropwise a solution of benzaldehyde (4.5 g) in THF (100 ml). The temperature is raised to room temperature after 30 minutes of stirring at the same temperature. Add saturated ammonium chloride solution (300ml) and separate layers. The organic layer is separated to remove moisture and concentrated under reduced pressure. MC (300ml) was added to the residue, followed by PCC (17.25g), followed by stirring for 12 hours. The reaction solution was filtered, concentrated under reduced pressure, and recrystallized from a THF / methanol mixed solvent to obtain a labeled compound (6 g).
(2)테트라파라벤조일페닐실란(tetra-p-benzoylphenylsilane)의 합성(2) Synthesis of tetra-p-benzoylphenylsilane
둥근 바닥 플라스크에 테트라파라브로모페닐실란(tetra-p-bromophenyl silane) (6.52g)을 넣고 아르곤 분위기에서 용매인 THF(300ml)를 넣어 녹인다. 온도를 영하 78도로 유지하며, 1.6몰 BuLi 용액 (300ml)을 적가한다. 같은 온도에서 30분간 교반하고, THF(100ml)에 벤즈알데히드(4.5g)를 녹인 용액을 적가한다. 같은 온도에서 30분 교반 후 상온으로 온도를 상승시킨다. 염화암모늄 포화 용액 (300ml)를 넣고 층을 분리시킨다. 유기층을 분리하여 수분을 제거하고 감압 농축한다. 잔사에 MC(300ml)를 넣고 PCC(17.25g)를 넣은 다음 12시간 교반시킨다. 반응액을 여과하여 감압 농축하고, THF/메탄올 혼합용매에서 재결정하여 표지 화합물(7g)을 얻었다.Tetra-p-bromophenyl silane (6.52 g) is added to a round bottom flask and THF (300 ml) is dissolved in an argon atmosphere. The temperature is maintained at minus 78 degrees and 1.6 molar BuLi solution (300 ml) is added dropwise. Stir at the same temperature for 30 minutes and add dropwise a solution of benzaldehyde (4.5 g) in THF (100 ml). The temperature is raised to room temperature after 30 minutes of stirring at the same temperature. Add saturated ammonium chloride solution (300ml) and separate layers. The organic layer is separated to remove moisture and concentrated under reduced pressure. MC (300ml) was added to the residue, followed by PCC (17.25g), followed by stirring for 12 hours. The reaction solution was filtered, concentrated under reduced pressure, and recrystallized from a THF / methanol mixed solvent to obtain a labeled compound (7 g).
(3) 4,4'-비스(디에톡시포스포노메틸)-1,1'-비페닐(3) 4,4'-bis (diethoxyphosphonomethyl) -1,1'-biphenyl
(4,4'-bis(diethoxyphosphono- methyl)-1,1'-biphenyl)의 합성 Synthesis of (4,4'-bis (diethoxyphosphonomethyl) -1,1'-biphenyl)
에탄올(100 mL)에 4,4'-비스(브로모메틸)-1,1'-비페닐(34 g), 트리에틸포스파이트 (33.2 g)를 넣은 혼합용액을 24 시간 동안 환류시켰다. 혼합용액을 실온으로 냉각하여 용매를 감압 증류한 후, 반응 혼합물을 에틸아세테이트:헥산(1:1, 부피비)의 혼합용매로 재결정하여 표지 화합물(43 g)을 얻었다.A mixed solution of 4,4'-bis (bromomethyl) -1,1'-biphenyl (34 g) and triethylphosphite (33.2 g) was added to ethanol (100 mL) for 24 hours. The mixed solution was cooled to room temperature, the solvent was distilled off under reduced pressure, and the reaction mixture was recrystallized from a mixed solvent of ethyl acetate: hexane (1: 1, volume ratio) to obtain a labeled compound (43 g).
(4)[4'-(2,2-디페닐비닐)비페닐-4-메틸]인산 디에틸 에스테르(4) [4 '-(2,2-diphenylvinyl) biphenyl-4-methyl] phosphate diethyl ester
([4'-(2,2-Diphenyl-vinyl)-biphenyl-4-methyl]-phosphonic acid diethyl ester)의 합성 Synthesis of ([4 '-(2,2-Diphenyl-vinyl) -biphenyl-4-methyl] -phosphonic acid diethyl ester)
질소 존재 하에 4,4'-비스(디에톡시포스포노메틸)-1,1'-비페닐 (9.1 g)을 THF(200 mL)에 녹인 후, 벤조페논 93.7 g)과 칼륨 t-부톡사이드 (5.6 g)을 첨가하여 40 ℃의 온도에서 24 시간동안 교반하였다. 혼합용액을 실온으로 냉각시켜 증류수 (200 mL)를 서서히 첨가한 다음, 이 용액에 에틸아세테이트 (200 mL)를 더 넣고 혼합 유기용매 층을 분리하였다. 유기용매 층을 무수 황산마그네슘으로 건조, 증류한 다음, 반응혼합물을 디클로로메탄으로 재결정하여 흰색 고체의 표지 화합물(10g)을 얻었다.4,4'-bis (diethoxyphosphonomethyl) -1,1'-biphenyl (9.1 g) was dissolved in THF (200 mL) in the presence of nitrogen, followed by 93.7 g of benzophenone and potassium t-butoxide ( 5.6 g) was added and stirred at a temperature of 40 ° C for 24 h. The mixed solution was cooled to room temperature, distilled water (200 mL) was added slowly, and then ethyl acetate (200 mL) was added to the solution, and the mixed organic solvent layer was separated. The organic solvent layer was dried over anhydrous magnesium sulfate, distilled, and the reaction mixture was recrystallized with dichloromethane to obtain a white solid labeled compound (10 g).
(5)테트라키스[4-((E)-2-(4'-(2,2-디페닐비닐)비페닐-4-일)-1-페닐비닐) 페닐]메탄(tetrakis[4-((E)-2-(4'-(2,2-diphenylvinyl)biphenyl-4- yl)-1-phenylvinyl)pheny]methane)의 합성(5) tetrakis [4-((E) -2- (4 '-(2,2-diphenylvinyl) biphenyl-4-yl) -1-phenylvinyl) phenyl] methane (tetrakis [4- ( Synthesis of (E) -2- (4 '-(2,2-diphenylvinyl) biphenyl-4-yl) -1-phenylvinyl) pheny] methane)
질소 존재 하에서 상기 단계 (1)에서 합성한 테트라파라벤조일페닐메탄(7.3g)과 상기 단계 (4)에서 합성한 [4'-(2,2-디페닐비닐)비페닐-4-메틸]인산 디에틸 에스테르(25g)를 THF(200 mL)에 녹인 후 칼륨 t-부톡사이드 (15.6 g)을 첨가하여 40 ℃의 온도에서 24 시간동안 교반하였다. 혼합용액을 실온으로 냉각시켜 증류수 (200 mL)를 서서히 첨가한 다음, 이 용액에 에틸아세테이트 (200 mL)를 더 넣고 혼합 유기용매 층을 분리하였다. 유기용매 층을 무수 황산마그네슘으로 건조, 증류한 다음, 반응혼합물을 디클로로메탄으로 재결정하여 흰색 고체의 표지 화합물(11g)을 얻었다.Tetraparabenzoylphenylmethane (7.3 g) synthesized in step (1) in the presence of nitrogen and [4 '-(2,2-diphenylvinyl) biphenyl-4-methyl] phosphate synthesized in step (4) Diethyl ester (25 g) was dissolved in THF (200 mL), and potassium t-butoxide (15.6 g) was added and stirred at a temperature of 40 ° C. for 24 hours. The mixed solution was cooled to room temperature, distilled water (200 mL) was added slowly, and then ethyl acetate (200 mL) was added to the solution, and the mixed organic solvent layer was separated. The organic solvent layer was dried over anhydrous magnesium sulfate, distilled, and the reaction mixture was recrystallized with dichloromethane to obtain a white solid labeled compound (11 g).
(6)테트라키스[4-((E)-2-(4'-(2,2-디페닐비닐)비페닐-4-일)-1-페닐비닐) 페닐]실란(tetrakis[4-((E)-2-(4'-(2,2-diphenylvinyl)biphenyl- 4-yl)-1-phenylvinyl)phenyl]silane)의 합성(6) tetrakis [4-((E) -2- (4 '-(2,2-diphenylvinyl) biphenyl-4-yl) -1-phenylvinyl) phenyl] silane (tetrakis [4- ( Synthesis of (E) -2- (4 '-(2,2-diphenylvinyl) biphenyl-4-yl) -1-phenylvinyl) phenyl] silane)
질소 존재 하에서 상기 단계 (2)에서 합성한 테트라파라벤조일페닐실란(7.5g)과 상기 단계 (4)에서 합성한 [4'-(2,2-디페닐비닐)비페닐-4-메틸]인산 디에틸 에스테르(25g)를 THF(200 mL)에 녹인 후 칼륨 t-부톡사이드 (5.6 g)을 첨가하여 40 ℃의 온도에서 24 시간동안 교반하였다. 혼합용액을 실온으로 냉각시켜 증류수 (200 mL)를 서서히 첨가한 다음, 이 용액에 에틸아세테이트 (200 mL)를 더 넣고 혼합 유기용매 층을 분리하였다. 유기용매 층을 무수 황산마그네슘으로 건조, 증류한 다음, 반응혼합물을 디클로로메탄으로 재결정하여 흰색 고체의 표지 화합물(12g)을 얻었다.Tetraparabenzoylphenylsilane (7.5 g) synthesized in step (2) in the presence of nitrogen and [4 '-(2,2-diphenylvinyl) biphenyl-4-methyl] phosphate synthesized in step (4) Diethyl ester (25 g) was dissolved in THF (200 mL), and potassium t-butoxide (5.6 g) was added and stirred at a temperature of 40 ° C. for 24 hours. The mixed solution was cooled to room temperature, distilled water (200 mL) was added slowly, and then ethyl acetate (200 mL) was added to the solution, and the mixed organic solvent layer was separated. The organic solvent layer was dried over anhydrous magnesium sulfate, distilled, and the reaction mixture was recrystallized with dichloromethane to obtain a white solid labeled compound (12 g).
이상에서 상세히 설명한 바와 같이, 본 발명은 유기발광체의 청색발광물질로서 상기와 같은 Th 구조의 화합물을 사용하여 발광색 및 소자의 안정성이 우수하고 발광효율도 증가된 유기전계발광 소자를 얻을 수 있다. As described in detail above, the present invention can obtain an organic electroluminescent device having excellent emission color and stability and improved luminous efficiency by using a compound having a Th structure as the blue light emitting material of the organic light emitting material.
이상 설명한 내용을 통해 당업자라면 본 발명의 기술사상을 일탈하지 않는 범위에서 다양한 변경 및 응용이 가능하다. 따라서 본 발명의 기술적 범위는 실시 예에 개재된 내용으로 한정되는 것이 아니라 특허 청구의 범위에 의해 정해져야만 한다. Various changes and applications may be made by those skilled in the art through the above description without departing from the technical spirit of the present invention. Therefore, the technical scope of the present invention should not be limited to the contents disclosed in the embodiments, but should be defined by the claims.
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