KR101567784B1 - Solution-Processable Novel Iridium(III) Complexes and Organic Light-Emitting Diodes Containing the same - Google Patents

Solution-Processable Novel Iridium(III) Complexes and Organic Light-Emitting Diodes Containing the same Download PDF

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KR101567784B1
KR101567784B1 KR1020140021930A KR20140021930A KR101567784B1 KR 101567784 B1 KR101567784 B1 KR 101567784B1 KR 1020140021930 A KR1020140021930 A KR 1020140021930A KR 20140021930 A KR20140021930 A KR 20140021930A KR 101567784 B1 KR101567784 B1 KR 101567784B1
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iridium
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진성호
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부산대학교 산학협력단
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Abstract

본 발명은 용액공정이 가능한 신규한 이리듐(III) 착화합물 및 이를 포함하는 유기전계발광소자에 관한 것으로, 보다 상세하게는, 주리간드로서 퀴놀린 및 티오펜 유도체가 도입되어 있고 보조리간드로 피콜리닉산의 질소 원자에 대하여 파라 위치에 할로겐 유도체 또는 전자수송 특성을 나타내는 옥사디아졸 유도체가 치환된 피콜리닉산 유도체가 도입된 신규한 이리듐(III) 착화합물 및 상기 이리듐(III) 착화합물을 포함하는 유기전계발광소자에 관한 것이다.
본 발명에 따른 이리듐(III) 착화합물은 전기적 안정성이 우수하고, 높은 발광 특성과 휘도를 가지며 색순도 구현이 가능한 적색 인광 발광 화합물로, 유기용매에 대한 향상된 가용성과 내열성으로 전극과의 계면 특성이 우수해 유기전계발광소자의 발색재료로서 유용하다.The present invention relates to a novel iridium (III) complex compound capable of solution processing and an organic electroluminescent device comprising the same. More particularly, the present invention relates to a novel iridium (III) complex compound having quinoline and thiophene derivatives as main ligands and picolinic acid A novel iridium (III) complex in which a picolinic acid derivative substituted with a halogen derivative or an oxadiazole derivative showing an electron transporting property is introduced at the para position relative to the nitrogen atom, and an organic electroluminescent device including the iridium (III) .
The iridium (III) complex according to the present invention is a red phosphorescent compound which is excellent in electrical stability, has high luminescence characteristics and brightness, and can realize color purity. It has excellent interfacial property with electrodes due to its improved solubility and heat resistance to organic solvents And is useful as a coloring material for an organic electroluminescent device.

Description

용액공정이 가능한 신규한 이리듐(ＩＩＩ) 착화합물 및 이를 포함하는 유기전계발광소자{Solution-Processable Novel Iridium(III) Complexes and Organic Light-Emitting Diodes Containing the same}[0001] The present invention relates to a novel iridium (III) complex compound capable of solution process and an organic electroluminescent device comprising the same.

본 발명은 용액공정이 가능한 신규한 이리듐(III) 착화합물 및 이를 포함하는 유기전계발광소자에 관한 것으로, 보다 상세하게는, 주리간드로서 퀴놀린 및 티오펜 유도체가 도입되어 있고 보조리간드로 피콜리닉산의 질소 원자에 대하여 파라 위치에 할로겐 유도체 또는 전자수송 특성을 나타내는 옥사디아졸 유도체가 치환된 피콜리닉산 유도체가 도입된 신규한 이리듐(III) 착화합물 및 상기 이리듐(III) 착화합물을 포함하는 유기전계발광소자에 관한 것이다.The present invention relates to a novel iridium (III) complex compound capable of solution processing and an organic electroluminescent device comprising the same. More particularly, the present invention relates to a novel iridium (III) complex compound having quinoline and thiophene derivatives as main ligands and picolinic acid A novel iridium (III) complex in which a picolinic acid derivative substituted with a halogen derivative or an oxadiazole derivative showing an electron transporting property is introduced at the para position relative to the nitrogen atom, and an organic electroluminescent device including the iridium (III) .

최근에 디스플레이 장치의 대형화에 따라 액정표시장치(liquid crystal display, LCD), 플라즈마디스플레이패널(plasma display panel, PDP) 등의 평면표시장치의 요구가 증가하고 있다. 이들 평면표시장치는 CRT와 비교하여 응답속도가 느리고 시야각의 제한이 있어서, 다른 표시장치에 대한 연구가 진행되고 있는데, 그 중의 하나가 전계발광소자이다.2. Description of the Related Art Recently, as the size of a display device has been increased, a demand for a flat display device such as a liquid crystal display (LCD), a plasma display panel (PDP) and the like has increased. These planar display devices are slower in response speed than CRTs and have limited viewing angles, and research on other display devices is underway, one of which is an electroluminescent device.

종래 전계발광소자로는 ZnS, CaS 등의 p-n 접합으로 이루어진 무기물 반도체에 전계를 가했을 경우에 일어나는 발광상을 이용한 무기계 전계발광소자가 주로 사용되었으나, 무기계 전계발광소자의 경우 구동전압이 교류 220V 이상이 요구되고, 소자가 진공상태에서 제작되기 때문에 대형화가 어렵고, 특히 고효율의 청색을 얻기 곤란한 문제점이 있었다.Conventionally, an inorganic electroluminescent device using a luminescent phase which occurs when an electric field is applied to an inorganic semiconductor made of pn junction such as ZnS or CaS is used as a conventional electroluminescent device. However, in the case of an inorganic electroluminescent device, Since the device is fabricated in a vacuum state, it is difficult to increase the size of the device, and in particular, it is difficult to obtain a high-efficiency blue color.

이런 문제점으로 인하여 유기물질을 이용한 유기전계발광소자(Organic Light-Emitting Diode, OLED)에 대한 연구가 진행되고 있다. 유기전계발광소자는 스스로 발광하는 유기물질을 이용한 디스플레이로서, 유기물질에 전기장을 걸어주면 전자(electron) 및 정공(hole)이 각각 음극 및 양극에서 전달되어 유기물질 내에서 결합하고, 이때 생성되는 에너지가 빛으로 방출되는 유기물 전기발광을 이용한다. 유기전계발광소자는 LCD 등과 비교할 때 시야각이 양호하고 소비전력이 낮을 뿐만 아니라 응답속도가 크게 개선되어 고화질의 영상을 처리할 수 있기 때문에 차세대 디스플레이 소자로 각광을 받고 있다. Organic light-emitting diodes (OLEDs) using organic materials have been studied due to such problems. An organic electroluminescent device is a display using an organic material that emits light by itself. When an electric field is applied to an organic material, electrons and holes are transmitted from the cathode and the anode, respectively, and are bonded in the organic material. Lt; RTI ID = 0.0 > electroluminescence < / RTI > The organic electroluminescent device has a better viewing angle, lower power consumption, and a significantly improved response speed as compared with LCDs and the like, and is capable of processing high-quality images.

이와 같은 유기전계발광소자에서 빛이 방출되는 현상은 크게 형광(fluorescence)과 인광(phosphorescence)으로 구분될 수 있는데, 형광이 유기 분자가 단일항(single) 여기상태로부터 바닥상태로 떨어질 때 빛을 방출하는 현상이라면 인광은 유기분자가 삼중항(triplet) 여기상태로부터 바닥상태로 떨어질 때 빛을 방출하는 현상이다. The emission of light in such an organic electroluminescent device can be largely divided into fluorescence and phosphorescence. When fluorescence occurs, the organic molecules emit light when the organic molecules fall from a single excited state to a ground state. Phosphorescence is a phenomenon in which organic molecules emit light when they fall from a triplet excited state to a ground state.

이와 같이 유기전계발광소자의 발광 효율을 획기적으로 향상시킬 수 있는 인광용 유기전계발광소자(electrophosphorescence) 소자는 1999년 미국 프린스턴 대학의 S.R. Forrest 교수와 USC의 M.E. Thompson 교수팀에 의하여 개발되었는데, 특히 스핀-궤도 결합은 원자번호의 4제곱에 비례하므로 백금(Pt), 이리듐(Ir), 유로피움(Eu), 터븀(Tb) 등과 같은 무거운 원자의 착화합물이 인광 효율이 높은 것으로 알려져 있다. 백금 착화합물의 경우 가장 낮은 삼중항 엑시톤이 리간드에 중심을 두고 있는 ligand-centered 엑시톤(LC 엑시톤)이지만, 이리듐 착화합물은 가장 낮은 에너지를 갖는 삼중항 엑시톤이 중심금속-리간드 사이의 전하전달 상태(metal-ligand charge transfer, MLCT)이다. 따라서 이리듐 착화합물은 백금 착화합물과 비교하여 더 큰 스핀-궤도 결합을 형성하여 훨씬 짧은 삼중항 엑시톤 수명을 가지고 높은 인광 효율을 나타낸다.The organic electroluminescent device for phosphorescence capable of remarkably improving the luminous efficiency of the organic electroluminescent device is disclosed in S. R. Prof. Forrest and M.E. The spin-orbit coupling is proportional to the fourth power of the atomic number, so complex compounds of heavy atoms such as platinum (Pt), iridium (Ir), europium (Eu), and terbium (Tb) It is known that the efficiency is high. In the case of the platinum complex, the lowest triplet exciton is a ligand-centered exciton (LC exciton) centered at the ligand, whereas the iridium complex is the triplet exciton with the lowest energy, which is the metal- ligand charge transfer, MLCT). Therefore, the iridium complex forms a larger spin-orbit coupling as compared with the platinum complex, resulting in a higher phosphorescence efficiency with a shorter triplet exciton lifetime.

이와 관련하여 C. Adachi 등은 이리듐을 중심 금속으로 갖는 녹색 인광 색소인 bis(2-phenylpyridine)iridium(Ⅲ) acetylacetonate [(ppy)2Ir(acac)]를 3-phenyl-4-(1'-naphthyl)-5-phenyl-1,2,4-triazole(TAZ)에 도핑하여 최대 발광 효율 60 lm/W, 최대 내부 양자 효율이 87% 수준인 유기전계발광소자를 발표한 바 있다. 또한 미국 Universal Display Corp.(UDC)에서는 이와 같은 녹색 인광 색소를 발광층에 도핑하고, LG 화학에서 개발한 정공주입물질을 사용하여 82 lm/W의 높은 발광 효율을 달성하였다고 발표한 바 있다. In this connection, C. Adachi et al. Prepared bis (2-phenylpyridine) iridium (III) acetylacetonate [(ppy) 2 Ir (acac)], a green phosphorescent dye having iridium as a central metal, naphthyl) -5-phenyl-1,2,4-triazole (TAZ) to obtain a maximum luminous efficiency of 60 lm / W and a maximum internal quantum efficiency of 87%. In addition, US Universal Display Corp. (UDC) has announced that the green phosphorescent pigment is doped in the light emitting layer and a high luminous efficiency of 82 lm / W is achieved using the hole injecting material developed by LG Chem.

이와 같이 청색, 녹색과 적색을 나타내는 인광용 유기전계발광소자는 개발되어 있으나 현재까지 발광 효율, 색좌표 및 수명이 모두 우수한 삼원색의 인광용 유기전계발광소자는 아직 개발되어 있지 않다. 미국 등록특허 제7,250,512호와 같이, 적색의 발광색을 구현하는 Ir(btp)2(acac) (Iridium (Ⅲ) bis(2-(2'-benzothienyl)pyridinato-N,C2)(acetylacetonate)이라는 물질이 공개되어있다. 그러나, 아직까지 색순도, 효율 및 용해도 면에서 신규한 화합물이 여전히 요구되고 있다.Organic electroluminescent devices for phosphorescence exhibiting blue, green and red colors have been developed, but organic electroluminescent devices for phosphorescence for three primary colors having excellent luminous efficiency, color coordinates and lifetime have not yet been developed. A material called Ir (btp) 2 (acac) (Iridium (Ⅲ) bis (2- (2'-benzothienyl) pyridinato-N, C2) (acetylacetonate) which emits red luminescent color is disclosed in US Pat. No. 7,250,512 However, there is still a demand for a novel compound in terms of color purity, efficiency and solubility.

미국 등록특허 제7,250,512호United States Patent No. 7,250,512

본 발명은 전기적 안정성이 우수하고, 주리간드로서 퀴놀린 및 티오펜 유도체가 도입되어 있고 보조리간드로 피콜리닉산의 질소 원자에 대하여 파라 위치에 할로겐 유도체 또는 전자수송 특성을 나타내는 옥사디아졸 유도체가 치환된 피콜리닉산 유도체가 도입된 높은 발광 특성과 휘도를 가지며 색순도 구현이 가능한 신규한 용액공정이 가능한 이리듐(III) 적색 인광 발광 화합물을 제공하는 것이다.The present invention relates to a quinolinone compound having excellent electrical stability, quinoline and thiophene derivatives being introduced as main ligands, a quinoline and thiophene derivative being introduced as auxiliary ligands, a halogen derivative at the para position relative to the nitrogen atom of picolinic acid or an oxadiazole derivative (III) red phosphorescent light emitting compound capable of a novel solution process capable of realizing color purity and having high luminescence characteristics and luminance with picolinic acid derivatives incorporated therein.

또한 본 발명은 유기용매에 대한 향상 된 가용성과 내열성으로 전극과의 계면 특성이 우수한 상기 이리듐(III) 착화합물을 발색재료로서 채용한 유기전계발광소자를 제공하는 것이다.Another object of the present invention is to provide an organic electroluminescent device employing the iridium (III) complex, which has excellent interfacial characteristics with an electrode due to improved solubility and heat resistance to an organic solvent, as a coloring material.

본 발명은 하기 화학식 1로 표시되는 이리듐(III) 착화합물을 제공한다:The present invention provides an iridium (III) complex represented by the following Formula 1:

[화학식 1][Chemical Formula 1]

Figure 112014018388164-pat00001
Figure 112014018388164-pat00001

상기 화학식 1에서,In Formula 1,

Ar은 (C6-C20)아릴 또는 (C3-C20)헤테로아릴이며;Ar is (C6-C20) aryl or (C3-C20) heteroaryl;

Z는 O, S 또는 Se 이며;Z is O, S or Se;

R1은 수소, 할로겐, (C1-C20)알킬, (C1-C20)알콕시, 시아나이드 또는 니트로이며;R 1 is hydrogen, halogen, (C 1 -C 20) alkyl, (C 1 -C 20) alkoxy, cyanide or nitro;

R2는 할로겐 또는

Figure 112014018388164-pat00002
이고;R 2 is halogen or
Figure 112014018388164-pat00002
ego;

L1은 (C6-C20)아릴렌이고; L < 1 > is (C6-C20) arylene;

Ar1는 (C6-C20)아릴이고;Ar < 1 > is (C6-C20) aryl;

상기 Ar의 아릴 및 헤테로아릴은 서로 독립적으로 할로겐, 하이드록시, (C1-C10)알킬, (C1-C10)알콕시, (C3-C20)시클로알킬 및 (C6-C20)아릴로부터 선택되는 하나 이상의 치환기로 더 치환될 수 있으며;Wherein said aryl and heteroaryl of Ar is optionally substituted with one or more substituents independently selected from halogen, hydroxy, (C1-C10) alkyl, (C1-C10) alkoxy, (C3- C20) cycloalkyl and ≪ / RTI >

상기 헤테로아릴은 N, O 및 S로부터 선택되는 하나 이상의 헤테로원자를 포함한다. Wherein said heteroaryl comprises at least one heteroatom selected from N, O and S;

본 발명의 일실시예에 따른 상기 화학식 1의 이리듐(III) 착화합물에 있어서, 상기 Ar은 (C6-C20)아릴이며; Z는 S이며; R1은 수소이며; R2는 할로겐 또는

Figure 112014018388164-pat00003
이고; L1은 (C6-C20)아릴렌이고; Ar1는 (C6-C20)아릴일 수 있다.In the iridium (III) complex of Formula 1 according to an embodiment of the present invention, Ar is (C6-C20) aryl; Z is S; R 1 is hydrogen; R 2 is halogen or
Figure 112014018388164-pat00003
ego; L < 1 > is (C6-C20) arylene; Ar < 1 > may be (C6-C20) aryl.

본 발명의 일실시예에 따른 상기 화학식 1의 이리듐(III) 착화합물에 있어서, 상기 R2는 플루오로, 클로로, 브로모, 아이오도,

Figure 112014018388164-pat00004
또는
Figure 112014018388164-pat00005
일 수 있다.In the iridium (III) complex of Formula 1 according to an embodiment of the present invention, R 2 is fluoro, chloro, bromo, iodo,
Figure 112014018388164-pat00004
or
Figure 112014018388164-pat00005
Lt; / RTI >

본 발명의 일실시예에 따른 상기 화학식 1의 이리듐(III) 착화합물에 있어서, 하기 구조로부터 선택되는 이리듐(III) 착화합물일 수 있다.In the iridium (III) complex of Formula 1 according to an embodiment of the present invention, it may be an iridium (III) complex selected from the following structures.

Figure 112014018388164-pat00006

Figure 112014018388164-pat00006

또한, 본 발명은 상기 화학식 1의 이리듐(III) 착화합물을 발광층에 포함하는 유기전계발광소자를 제공한다.Also, the present invention provides an organic electroluminescent device comprising an iridium (III) complex compound of Formula 1 in a light emitting layer.

본 발명의 일실시예에 따른 유기전계발광소자에서, 제 1 전극과, 상기 제 1 전극과 대향적으로 형성된 제 2 전극을 포함하며, 상기 발광층은 상기 제 1 전극과 제 2 전극 사이에 적층되어 있을 수 있다.In an organic electroluminescent device according to an embodiment of the present invention, the organic electroluminescent device includes a first electrode and a second electrode opposed to the first electrode, wherein the light emitting layer is stacked between the first electrode and the second electrode Can be.

본 발명의 일실시예에 따른 유기전계발광소자에서, 상기 제 1 전극과 발광층 사이로 정공주입층 및 정공전달층을, 상기 발광층과 제 2 전극 사이로 전자전달층 및 전자전달층을 더욱 포함할 수 있다.The organic electroluminescent device according to an embodiment of the present invention may further include a hole injection layer and a hole transport layer between the first electrode and the light emitting layer and an electron transport layer and an electron transport layer between the light emitting layer and the second electrode .

본 발명의 일실시예에 따른 유기전계발광소자에서, 상기 이리듐(III) 착화합물을 발광층의 도판트로 포함될 수 있다.In the organic electroluminescent device according to an embodiment of the present invention, the iridium (III) complex may be included as a dopant of the light emitting layer.

본 발명의 일실시예에 따른 유기전계발광소자에서, 상기 이리듐(III) 착화합물은 발광층 총량을 기준으로 3 내지 20 중량% 의 농도로 포함될 수 있다.In the organic electroluminescent device according to an embodiment of the present invention, the iridium (III) complex may be contained at a concentration of 3 to 20 wt% based on the total amount of the light emitting layer.

본 발명에 따른 이리듐(III) 착화합물은 적색 인광 화합물로, 주리간드로서 퀴놀린 및 티오펜 유도체가 도입됨과 동시에 보조리간드로 피콜리닉산의 질소 원자에 대하여 파라 위치에 할로겐 유도체 또는 전자수송 특성을 나타내는 옥사디아졸 유도체가 치환된 피콜리닉산 유도체가 도입되어 있어 우수한 발광특성 및 휘도 특성을 갖을 뿐만 아니라 높은 색순도를 구현할 수 있다. 또한, 본 발명에 따른 이리듐(III) 착화합물은 유기용매에 대한 향상된 가용성과 내열성으로 전극과의 계면 특성이 우수하기 때문에 유기전계발광소자 제작시 용액공정이 가능하다.The iridium (III) complex compound according to the present invention is a red phosphorescent compound, in which quinoline and thiophene derivatives are introduced as main ligands, and a halogen derivative at para position relative to the nitrogen atom of picolinic acid as an auxiliary ligand, A picolinic acid derivative substituted with a diazole derivative is introduced to have excellent light emitting properties and luminance characteristics as well as high color purity. In addition, the iridium (III) complex according to the present invention has excellent interfacial characteristics with the electrode due to its improved solubility and heat resistance to an organic solvent, so that a solution process can be performed in the fabrication of an organic electroluminescent device.

도 1 - 본 발명에 따라 합성된 이리듐 착화합물이 적용된 단일층 형태의 유기전계발광소자를 도시한 단면도
도 2 - 본 발명에 따라 합성된 이리듐 착화합물이 적용된 다층 형태의 유기전계발광소자를 개략적으로 도시한 단면도
도 3 - 본 발명의 실시예 2에 따라 합성된 이리듐 착화합물 (Th-PQ)2Ir(4-OXD-pic)에 대한 UV-visible 흡수 스펙트럼 측정 결과를 도시한 그래프
도 4 - 본 발명의 실시예 2에 따라 합성된 이리듐 착화합물 (Th-PQ)2Ir(4-OXD-pic)에 대한 PL 발광 스펙트럼 측정 결과를 도시한 그래프
도 5 - 본 발명의 실시예 2에 따라 합성된 이리듐 착화합물 (Th-PQ)2Ir(4-OXD-pic)에 대한 EL 발광 스펙트럼 측정 결과를 도시한 그래프
도 6 - 본 발명의 실시예 2에 따라 합성된 이리듐 착화합물 (Th-PQ)2Ir(4-OXD-pic) 및 비교 이리듐 착화합물 (Th-PQ)2Ir(pic)에 대한 전압에 대한 전압-전류밀도-휘도 측정 결과를 도시한 그래프
도 7 - 본 발명의 실시예 2에 따라 합성된 이리듐 착화합물 (Th-PQ)2Ir(4-OXD-pic) 및 비교 이리듐 착화합물 (Th-PQ)2Ir(pic)에 대한 휘도에 대한 외부 양자효율 측정 결과를 도시한 그래프
도 8은 본 발명의 비교예인 Ir(btp)2(acac)에 대한 전류밀도에 대한 외부 양자효율 측정 결과를 도시한 그래프1 is a cross-sectional view illustrating a single layer type organic electroluminescent device to which an iridium complex compound synthesized according to the present invention is applied;
2 is a cross-sectional view schematically showing a multi-layer type organic electroluminescent device to which an iridium complex compound synthesized according to the present invention is applied
3 is a graph showing the results of measurement of UV-visible absorption spectra of an iridium complex (Th-PQ) 2 Ir (4-OXD-pic) synthesized according to Example 2 of the present invention
FIG. 4 is a graph showing the results of PL emission spectra of iridium complex (Th-PQ) 2 Ir (4-OXD-pic) synthesized according to Example 2 of the present invention
FIG. 5 is a graph showing the results of measurement of the EL luminescence spectrum of the iridium complex (Th-PQ) 2 Ir (4-OXD-pic) synthesized according to Example 2 of the present invention
6-voltage for the voltage on the iridium complex (Th-PQ) 2 Ir ( 4-OXD-pic) and Comparative iridium complex (Th-PQ) 2 Ir ( pic) synthesized according to a second embodiment of the present invention; Current density-graph showing the result of luminance measurement
Figure 7 - External quantum of luminance for the iridium complex (Th-PQ) 2 Ir (4-OXD-pic) and the comparative iridium complex (Th-PQ) 2 Ir (pic) synthesized according to Example 2 of the present invention Graph showing efficiency measurement result
8 is a graph showing the results of measurement of external quantum efficiency against current density for Ir (btp) 2 (acac) which is a comparative example of the present invention

본 발명은 용액공정이 가능한 신규한 이리듐(III) 착화합물 및 이를 포함하는 유기전계발광소자에 관한 것으로, 보다 상세하게는, 주리간드로서 퀴놀린 및 티오펜 유도체가 도입되어 있고 보조리간드로 피콜리닉산의 질소 원자에 대하여 파라 위치에 할로겐 유도체 또는 전자수송 특성을 나타내는 옥사디아졸 유도체가 치환된 피콜리닉산 유도체가 도입된 신규한 이리듐(III) 착화합물 및 상기 이리듐(III) 착화합물을 포함하는 유기전계발광소자에 관한 것이다.The present invention relates to a novel iridium (III) complex compound capable of solution processing and an organic electroluminescent device comprising the same. More particularly, the present invention relates to a novel iridium (III) complex compound having quinoline and thiophene derivatives as main ligands and picolinic acid A novel iridium (III) complex in which a picolinic acid derivative substituted with a halogen derivative or an oxadiazole derivative showing an electron transporting property is introduced at the para position relative to the nitrogen atom, and an organic electroluminescent device including the iridium (III) .

이하 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.

본 발명은 하기 화학식 1로 표시되는 이리듐(III) 착화합물을 제공한다:The present invention provides an iridium (III) complex represented by the following Formula 1:

[화학식 1][Chemical Formula 1]

Figure 112014018388164-pat00007
Figure 112014018388164-pat00007

상기 화학식 1에서,In Formula 1,

Ar은 (C6-C20)아릴 또는 (C3-C20)헤테로아릴이며;Ar is (C6-C20) aryl or (C3-C20) heteroaryl;

Z는 O, S 또는 Se 이며;Z is O, S or Se;

R1은 수소, 할로겐, (C1-C20)알킬, (C1-C20)알콕시, 시아나이드 또는 니트로이며;R 1 is hydrogen, halogen, (C 1 -C 20) alkyl, (C 1 -C 20) alkoxy, cyanide or nitro;

R2는 할로겐 또는

Figure 112014018388164-pat00008
이고;R 2 is halogen or
Figure 112014018388164-pat00008
ego;

L1은 (C6-C20)아릴렌이고; L < 1 > is (C6-C20) arylene;

Ar1는 (C6-C20)아릴이고;Ar < 1 > is (C6-C20) aryl;

상기 Ar의 아릴 및 헤테로아릴은 서로 독립적으로 할로겐, 하이드록시, (C1-C10)알킬, (C1-C10)알콕시, (C3-C20)시클로알킬 및 (C6-C20)아릴로부터 선택되는 하나 이상의 치환기로 더 치환될 수 있으며;Wherein said aryl and heteroaryl of Ar is optionally substituted with one or more substituents independently selected from halogen, hydroxy, (C1-C10) alkyl, (C1-C10) alkoxy, (C3- C20) cycloalkyl and ≪ / RTI >

상기 헤테로아릴은 N, O 및 S로부터 선택되는 하나 이상의 헤테로원자를 포함한다.
Wherein said heteroaryl comprises at least one heteroatom selected from N, O and S;

상기 화학식 1의 이리듐(III) 착화합물에서 바람직하게 상기 Ar은 (C6-C20)아릴이며; Z는 S이며; R1은 수소이며; R2는 할로겐 또는

Figure 112014018388164-pat00009
이고; L1은 (C6-C20)아릴렌이고; Ar1는 (C6-C20)아릴이다.In the iridium (III) complex of Formula 1, Ar is preferably (C6-C20) aryl; Z is S; R 1 is hydrogen; R 2 is halogen or
Figure 112014018388164-pat00009
ego; L < 1 > is (C6-C20) arylene; Ar 1 is (C6-C20) aryl.

상기 화학식 1의 이리듐(III) 착화합물에서 보다 바람직하게 상기 R2는 플루오로, 클로로, 브로모, 아이오도,

Figure 112014018388164-pat00010
또는
Figure 112014018388164-pat00011
이다.In the iridium (III) complex of Formula 1, R 2 is preferably fluoro, chloro, bromo, iodo,
Figure 112014018388164-pat00010
or
Figure 112014018388164-pat00011
to be.

구체적으로 본 발명에 따른 화학식 1의 이리듐(III) 착화합물은 다음 화합물로 나타낼 수 있으나 이에 한정이 있는 것은 아니다.Specifically, the iridium (III) complex of formula (1) according to the present invention can be represented by the following compounds, but is not limited thereto.

Figure 112014018388164-pat00012
Figure 112014018388164-pat00012

본 발명에 따른 화학식 1의 이리듐 착화합물은 주리간드로서 퀴놀린 및 티오펜 유도체가 도입됨과 동시에 보조리간드로 피콜리닉산의 질소 원자에 대하여 파라 위치에 할로겐 유도체 또는 전자수송 특성을 나타내는 옥사디아졸 유도체가 치환된 피콜리닉산 유도체가 도입되어 있어 발광색과 발광 효율이 크게 개선되었으며, 유기용매에 쉽게 용해될 수 있으므로 대면적의 발광 면적을 유지할 수 있을 뿐만 아니라 향상된 내열 특성과 더불어 전극과의 계면 특성이 매우 우수하며 박막 특성이 크게 우수한 발광 재료로 사용될 수 있다. 또한, 본 발명의 이리듐 착화합물은 순수한 적색 발광색을 구현할 수 있는 물질로서 이를 발광층의 도판트로 사용함으로써 적색의 용액공정이 가능한 인광용 유기전계발광소자를 제작할 수 있다.
The iridium complex of formula (I) according to the present invention is characterized in that quinoline and thiophene derivatives are introduced as main ligands, and a halogen derivative at the para position relative to the nitrogen atom of picolinic acid as an auxiliary ligand or an oxadiazole derivative The picolinic acid derivative has been introduced to greatly improve the luminescent color and luminous efficiency and can be easily dissolved in an organic solvent. Therefore, not only can the luminescent area of a large area be maintained, but also the excellent heat resistance characteristic and excellent interfacial property with the electrode And can be used as a light emitting material having excellent thin film characteristics. In addition, the iridium complex of the present invention can form a pure red luminescent color, and it can be used as a dopant of a luminescent layer, whereby an organic electroluminescent device for phosphorescence capable of red solution process can be manufactured.

또한, 본 발명은 상기 화학식 1의 이리듐(III) 착화합물을 발광층에 포함하는 유기전계발광소자를 제공한다.Also, the present invention provides an organic electroluminescent device comprising an iridium (III) complex compound of Formula 1 in a light emitting layer.

보다 더 구체적으로, 상기 유기전계발광소자는 제 1 전극과, 상기 제 1 전극과 대향적으로 형성된 제 2 전극을 포함하며, 상기 발광층은 상기 제 1 전극과 제 2 전극 사이에 적층되어 있는 유기전계발광소자일 수 있다. More specifically, the organic electroluminescent device includes a first electrode and a second electrode oppositely disposed to the first electrode, wherein the emission layer includes an organic electroluminescent layer stacked between the first electrode and the second electrode, Emitting device.

또한, 본 발명의 유기전계발광소자는 상기 제 1 전극과 발광층 사이로 정공주입층 및 정공전달층을, 상기 발광층과 제 2 전극 사이로 전자전달층 및 전자전달층을 더 포함할 수 있다.The organic electroluminescent device of the present invention may further include a hole injecting layer and a hole transporting layer between the first electrode and the light emitting layer, and an electron transporting layer and an electron transporting layer between the light emitting layer and the second electrode.

또한, 본 발명의 상기 이리듐(III) 착화합물은 발광층의 도판트로 포함될 수 있으며, 상기 이리듐(III) 착화합물은 발광층 총량을 기준으로 3 내지 20 중량%의 농도로 포함될 수 있다. 만약 3 내지 20 중량%의 농도를 초과하거나 부족하게 되면 발광층의 도판트의 응집(aggregation) 또는 희석(dilution) 효과에 의해서 효율이 매우 낮으며, 발광층의 상분리에 의해서 박막의 특성이 매우 나쁘게 되며, 그 결과 발광효율 등의 특성이 매우 떨어지게 된다. In addition, the iridium (III) complex of the present invention may be included as a dopant of the light emitting layer, and the iridium (III) complex may be contained in a concentration of 3 to 20 wt% based on the total amount of the light emitting layer. If the concentration is in excess of 3 to 20% by weight, the efficiency is very low due to the aggregation or dilution effect of the dopant of the light emitting layer, and the characteristics of the thin film are deteriorated due to the phase separation of the light emitting layer, As a result, the characteristics such as the luminous efficiency become very low.

이하, 본 발명에 따른 유기전계발광소자의 제조방법을 살펴보기로 한다.Hereinafter, a method of manufacturing an organic electroluminescent device according to the present invention will be described.

도 1은 본 발명의 일 실시예에 따라 상술한 이리듐 착화합물이 적용될 수 있는 단층 형태의 유기전계발광소자(1000)를 개략적으로 도시한 것이다. 이와 같은 단층 형태의 유기전계발광소자(1000)는 기판(1100), 제 1 전극(1110), 발광층(1140) 및 제 2 전극(1170)이 순차적으로 적층된 구조를 갖는다. 상기 기판(1100)은 예를 들어 유기(glass) 또는 플라스틱과 같은 물질로 제조될 수 있다. FIG. 1 schematically shows a single-layer type organic electroluminescent device 1000 to which the above-described iridium complex can be applied according to an embodiment of the present invention. The organic electroluminescent device 1000 having a single layer structure has a structure in which a substrate 1100, a first electrode 1110, a light emitting layer 1140, and a second electrode 1170 are sequentially stacked. The substrate 1100 may be made of materials such as, for example, glass or plastic.

구체적으로, 상기 제 1 전극(1110)으로는 ITO(indium-tin oxide), FTO(Fluorine doped tin oxide), ZnO-Ga2O3, 또는 ZnO-Al2O3, SnO2-Sb2O3 등과 같은 혼합 금속산화물, 폴리아닐린(polyaniline), 폴리티오펜(polythiophene) 등의 전도성 고분자 등의 물질이 사용될 수 있으며, 바람직한 실시예에 따르면 ITO이다. In particular, the first electrode 1110 may be formed of indium tin oxide (ITO), fluorine doped tin oxide (FTO), ZnO-Ga 2 O 3 , or ZnO-Al 2 O 3 , SnO 2 -Sb 2 O 3 And conductive polymers such as polyaniline and polythiophene may be used. According to a preferred embodiment, ITO is used.

그리고, 제 2 전극(1170)은 음전하 캐리어(negative-charged carrier)인 전자(electron)를 주입하는데 효과적인 물질로서 금, 알루미늄, 구리, 은, 또는 이들의 합금; 칼슘/알루미늄 합금, 마그네슘/은 합금, 알루미늄/리튬 합금 등과 같이 알루미늄, 인듐, 칼슘, 바륨, 마그네슘 및 이들이 조합된 합금; 또는 경우에 따라서는 희토류, 란탄족(lanthanide), 악티늄족(actinide)에 속하는 금속에서 선택될 수 있으며, 바람직하게는 알루미늄, 또는 알루미늄/칼슘 합금이다. The second electrode 1170 is an effective material for injecting electrons, which are negative-charged carriers, and is formed of gold, aluminum, copper, silver, or an alloy thereof; Aluminum, indium, calcium, barium, magnesium and alloys thereof, such as calcium / aluminum alloys, magnesium / silver alloys, aluminum / lithium alloys and the like; Or a metal belonging to rare earth, lanthanide or actinide, preferably aluminum, or aluminum / calcium alloy.

본 발명과 관련하여 사용될 수 있는 인광 특성을 갖는 호스트로는 아릴아민계(aryl amine), 카바졸계, 스파이로(spiro)계를 포함한다. 구체적으로는 4,4-N,N-디카바졸-비페닐(4,4-N,N-dicarbazole-biphenyl, CBP), N,N-디카바조일-3,5-벤젠(N,N-dicarbazoyl-3,5-benzene, mCP), 폴리비닐카바졸(poly(vinylcarbazole), PVK), 폴리플루오렌, 4,4'-비스[9-(3,6비페닐카바졸일)]-1-1,1'-비페닐4,4'-비스[9-(3,6-비페닐카바졸일)]-1-1,1'-비페닐, 9,10-비스[(2',7'-t-부틸)-9',9''-스파이로비플루오레닐(spirobifluorenyl)안트라센, 테트라플루오렌(tetrafluorene) 등의 물질을 포함할 수 있으며, 바람직하게는 CBP 및 mCP를 사용할 수 있다. Hosts having phosphorescent properties that may be used in connection with the present invention include aryl amines, carbazole, spiro. Specific examples thereof include 4,4-N, N-dicarbazole-biphenyl, CBP, N, N-dicarbazoyl- dicarbazoyl-3,5-benzene, mCP), poly (vinylcarbazole) PVK, polyfluorene, 4,4'-bis [9- (3,6- biphenylcarbazolyl) Biphenyl 4,4'-bis [9- (3,6-biphenylcarbazolyl)] -1,1'-biphenyl, 9,10-bis [(2 ', 7' -t-butyl) -9 ', 9 "-spirobifluorenyl anthracene, tetrafluorene, and the like. Preferably, CBP and mCP may be used.

본 발명의 발광층(1140)은 대략 5~200㎚, 바람직하게는 50~100㎚의 두께로 제 1 전극(1110)의 상부로 적층되는데, 본 발명에 따른 이리듐 착화합물은 도판트로서 발광층(1140)에 대하여 3 내지 20 중량%, 보다 더 구체적으로 5 내지 20중량% 로 포함 될 수 있다.The light emitting layer 1140 of the present invention is laminated on top of the first electrode 1110 to a thickness of approximately 5 to 200 nm, preferably 50 to 100 nm. The iridium complex according to the present invention may include a light emitting layer 1140 as a dopant, By weight, more specifically from 5 to 20% by weight, based on the total weight of the composition.

한편, 본 발명에 따른 이리듐 착화합물은 상술한 단층 형태의 유기전계발광소자(1000)는 물론이고, 발광층과 전극 사이에 전자/정공 수송을 위한 별도의 층이 구비되어 있는 다층 형태의 유기전계발광소자에도 적용될 수 있는데, 도 2는 본 발명에 따라 합성된 이리듐 착화합물이 적용될 수 있는 다층 형태의 유기전계발광소자(2000)의 단면을 개략적으로 도시한 것이다. 도시된 것과 같이, 유기전계발광소자(2000)는 기판(2100), 제 1 전극(2110), 정공주입층(hole injection layer, HIL, 2120), 정공전달층(hole transporting layer, HTL, 2130), 발광층(2140), 전자전달층(electron transporting layer, ETL, 2150), 전자주입층(electron injection layer, EIL, 2160), 제 2 전극(2170)이 순차적으로 적층된 형태를 갖는다. Meanwhile, the iridium complex according to the present invention includes not only the single layer organic electroluminescent device 1000 described above but also a multi-layer organic electroluminescent device having a separate layer for electron / hole transport between the light emitting layer and the electrode. FIG. 2 schematically shows a cross section of a multilayer organic electroluminescent device 2000 to which an iridium complex compound synthesized according to the present invention can be applied. The organic electroluminescent device 2000 includes a substrate 2100, a first electrode 2110, a hole injection layer (HIL) 2120, a hole transporting layer (HTL) 2130, A light emitting layer 2140, an electron transporting layer (ETL) 2150, an electron injection layer (EIL) 2160, and a second electrode 2170 are sequentially stacked.

이와 같이 구성되는 다층 형태의 유기전계발광소자(2000)에 있어서 제 1 전극(2110)과 발광층(2140) 사이에 적층되는 정공주입층(2120)은 제 1 전극(2100)으로 사용되는 ITO와 정공전달층(2130)으로 사용되는 유기물질 사이의 계면 특성을 개선할 뿐만 아니라 그 표면이 평탄하지 않은 ITO의 상부에 도포되어 ITO의 표면을 부드럽게 만들어주는 기능을 한다. 특히 정공주입층(2120)은 제 1 전극(2110)으로 사용될 수 있는 ITO의 일함수 수준과 정공전달층(2130)의 HOMO 수준의 차이를 조절하기 위하여 ITO의 일함수 수준과 정공전달층(2130)의 HOMO 수준의 중간값을 가지는 물질로서, 특히 적절한 전도성을 갖는 물질을 선택한다. 본 발명과 관련하여 정공주입층(2120)을 이루는 물질로는 copper phthlalocyanine(CuPc), N,N'-dinaphthyl-N,N'-phenyl-(1,1'-biphenyl)-4,4'-diamine, NPD), 4,4',4''-tris[methylphenyl(phenyl)amino] triphenyl amine(m-MTDATA), 4,4',4''-tris[1-naphthyl(phenyl)amino] triphenyl amine(1-TNATA), 4,4',4''-tris[2-naphthyl(phenyl)amino] triphenyl amine(2-TNATA), 1,3,5-tris[N-(4-diphenylaminophenyl)phenylamino] benzene(p-DPA-TDAB) 등과 같은 방향족 아민류, 전도성 고분자로서의 폴리티오펜 유도체인 poly(3,4-ethylenedioxythiophene)-poly(styrnesulfonate)(PEDOT)를 사용할 수 있는데, 본 발명의 실시예에서는 PEDOT를 사용하였다. 정공주입층(2120)은 20~200Å의 두께로 제 1 전극(2110)의 상부에 코팅될 수 있다. The hole injection layer 2120 stacked between the first electrode 2110 and the light emitting layer 2140 in the multilayer organic electroluminescent device 2000 may be formed of ITO used as the first electrode 2100, Not only improves the interfacial property between the organic materials used as the transfer layer 2130 but also functions to smooth the surface of the ITO by being coated on the upper surface of the ITO whose surface is not flat. In particular, the hole injection layer 2120 may be formed by adjusting the work function level of the ITO and the hole transport layer 2130 to adjust the difference between the work function level of ITO and the HOMO level of the hole transport layer 2130, ) ≪ / RTI > as the material having a median value of the HOMO level. The hole injecting layer 2120 may be made of copper phthalocyanine (CuPc), N, N'-dinaphthyl-N, N'-phenyl- (1,1'- diamine, NPD), 4,4 ', 4' '- tris [methylphenyl (phenyl) amino] triphenyl amine (m-MTDATA), 4,4' (1-TNATA), 4,4 ', 4 "-tris [2-naphthyl (phenyl) amino] triphenyl amine (2-TNATA), 1,3,5-tris [N- (4-diphenylaminophenyl) phenylamino benzene (p-DPA-TDAB), poly (3,4-ethylenedioxythiophene) -poly (styrnesulfonate) (PEDOT) which is a polythiophene derivative as a conductive polymer can be used. In the embodiment of the present invention, PEDOT Were used. The hole injection layer 2120 may be coated on the first electrode 2110 to a thickness of 20 to 200 ANGSTROM.

한편, 정공주입층(2120)의 상부에는 정공주입층(2120)을 통하여 들어온 정공을 안정적으로 발광층(2140)으로 공급할 수 있도록 정공전달층(2130)이 형성되는데, 정공이 원활하게 수송, 전달될 수 있도록 정공전달층(2130)의 HOMO 수준이 발광층(2140)의 HOMO 수준보다 높은 물질이 선택된다. 본 발명과 간련하여 정공전달층(2130)에 사용될 수 있는 물질로는 N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-diphenyl-4,4'-diamine(TPD), N,N'-bis(1-naphthyl)-N,N'-biphenyl-[1,1'-biphenyl]-4,4'-diamine(TPB), N, N'-di(naphthalene-1-yl)-N, N'-diphenyl-benzidene, NPB), 트리페닐아민(TPA), bis[4-(N,N-diethylamino)-2-methylphenyl](4-methylphenyl) methane(MPMP), N,N,N',N'-tetrakis(4-methylphenyl)-(1,1'-biphenyl)-4,4-diamine(TTB), N,N'-bis(4-methylphenyl)-N,N'-bis(4-ethylphenyl)-[1,1'-(3,3'-dimethyl)biphenyl]-4,4'-diamine(ETPD) 등과 같은 저분자 정공 전달 물질과; 폴리비닐카바졸, 폴리아닐린, (페닐메닐)폴리실란 등의 고분자 정공 전달 물질이 사용될 수 있다. 본 발명의 실시예 1과 2에 따르면 정공전달층(2130)으로 NPB를 사용하였으며, 정공주입층(2130)은 약 10~100 ㎚의 두께로 정공주입층(2120)의 상부로 증착될 수 있다. A hole transporting layer 2130 is formed on the hole injecting layer 2120 so that the holes introduced through the hole injecting layer 2120 can be stably supplied to the light emitting layer 2140. A material whose HOMO level of the hole transport layer 2130 is higher than the HOMO level of the light emitting layer 2140 is selected. In connection with the present invention, materials usable for the hole transport layer 2130 include N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1,1'- diamine (TPD), N, N'-bis (1-naphthyl) -N, N'-biphenyl- [1,1'-biphenyl] -4,4'- bis (4-methylphenyl) methane (MPMP), bis [4- (N, N-diethylamino) -2-methylphenyl] ), N, N'-bis (4-methylphenyl) -N (N, N ', N'-tetrakis A low molecular weight hole transporting material such as N'-bis (4-ethylphenyl) - [1,1 '- (3,3'- dimethyl) biphenyl] -4,4'-diamine (ETPD); Polymeric hole transporting materials such as polyvinylcarbazole, polyaniline, and (phenylmethyl) polysilane can be used. According to embodiments 1 and 2 of the present invention, NPB is used as the hole transport layer 2130, and the hole injection layer 2130 may be deposited on the hole injection layer 2120 to a thickness of about 10 to 100 nm .

본 발명에 따르면 발광층(2140)과 제 2 전극(2170) 사이로 정공주입층(2120) 및 정공전달층(2130)에 대응될 수 있는 전자주입층(2160) 및 전자전달층(2150)이 형성된다. 전자주입층(2160)은 원활한 전자 주입을 유도하기 위한 것으로, 다른 전하 이동층과 달리 LiF, BaF2, CsF 등과 같이 알칼리 금속 또는 알칼리토류 금속 이온 형태가 사용되는데, 이들 금속 양이온에 의하여 전자전달층(2150)에 대한 도핑을 유도할 수 있도록 구성될 수 있다. An electron injecting layer 2160 and an electron transporting layer 2150 which correspond to the hole injecting layer 2120 and the hole transporting layer 2130 are formed between the light emitting layer 2140 and the second electrode 2170 . Unlike the other charge transporting layers, the electron injection layer 2160 is used to induce smooth electron injection. In contrast to other charge transporting layers, alkali metal or alkaline earth metal ion forms such as LiF, BaF 2 , and CsF are used. Gt; 2150 < / RTI >

전자전달층(2150)은 주로 전자를 끌어당기는 화학 성분이 포함된 재료로 구성되는데, 이를 위해서는 높은 전자 이동도가 요구되며 원활한 전자 수송을 통하여 발광층(2140)으로 전자를 안정적으로 공급한다. 본 발명에 따라 사용될 수 있는 전자전달층으로는 Alq3 및 옥사디아졸(oxadizole) 성분을 포함한다. 구체적으로는 Tris(8-hydroxyquinolinato)aluminum(Alq3); 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline(DDPA); 2-(4-biphenyl)-5-(4-tert-butyl)-1,3,4-oxadizole(PBD), 3-(4-biphenyl)-4-phenyl-5-(4-tert-butyl)-1,2,4-triazole(TAZ)과 같은 아졸 화합물; phenylquinozaline; 3,3'-[5'-[3-(3-Pyridinyl)phenyl] [1,1':3',1''-terphenyl]-3,3''-diyl] bispyridine (TmPyPB) 등을 포함한다. 본 발명의 실시예에서는 TmPyPB를 전자전달층(2150)으로 사용하였으며, 전자전달층(2150)은 5~150 ㎚의 두께로 발광층(2140)의 상부에 적층될 수 있다.
The electron transport layer 2150 is mainly composed of a material containing a chemical component that attracts electrons, which requires high electron mobility and stably supplies electrons to the light emitting layer 2140 through smooth electron transport. The electron transport layer that can be used in accordance with the present invention includes Alq 3 and oxadizole components. Specifically, Tris (8-hydroxyquinolinato) aluminum (Alq 3 ); 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (DDPA); 2- (4-biphenyl) -5- (4-tert-butyl) -1,3,4-oxadisole (PBD) Azole compounds such as 1,2,4-triazole (TAZ); phenylquinazoline; 3,3 ', 5'- [3- (3-Pyridinyl) phenyl] [1,1': 3 ', 1 "-terphenyl] -3,3'-diyl bispyridine (TmPyPB) do. In the embodiment of the present invention, TmPyPB is used as the electron transporting layer 2150, and the electron transporting layer 2150 may be deposited on the upper part of the light emitting layer 2140 with a thickness of 5 to 150 nm.

이하, 본 발명을 제조예 및 실시예에 의거하여 본 발명에 따른 신규한 이리듐(III) 착화합물, 이의 제조방법 및 소자의 발광특성을 예시하나, 하기의 실시예들은 본 발명에 대한 이해를 돕기 위한 것으로서, 본 발명의 범위가 하기의 실시예에 한정되는 것은 아니다.
Hereinafter, exemplary embodiments of the present invention will be described in detail with reference to the accompanying drawings, wherein like numerals are used to designate novel iridium (III) complexes according to the present invention, And the scope of the present invention is not limited to the following examples.

[제조예 1] 염소- 가교화 이합체(chloride-bridged dimer)의 제조 [Preparation Example 1] Chlorine- crosslinking Preparation of chloride-bridged dimer

Figure 112014018388164-pat00013
Figure 112014018388164-pat00013

4-4- 페닐Phenyl -2-(티오펜-2-일)퀴놀린의 제조-2- (thiophen-2-yl) quinoline

삼구 플라스크에 1-(티오펜-2-일)에타논 (1.43 g, 11.3 mmol), 2-아미노벤조페논 (2-aminobenzophenone, 2.46 g, 12.5 mmol), 디페닐포스페이트 (diphenyl phosphate, 3.41 g, 13.6 mmol), 메타크레졸 (m-cresol, 8.0 mL)를 넣고 질소분위기에서 상온에서 20분 동안 교반 후 다시 12시간 동안 환류시켰다. 삼구 플라스크를 상온으로 냉각시킨 후 메틸렌 클로라이드 (methylene chloride, 60 mL)와 10% 수산화나트륨 (NaOH) 수용액을 첨가한 후 유기층을 분리하였다. 얻어진 유기층은 증류수로 여러번 세척 후 황산마그네슘을 이용하여 건조 시킨 뒤 헥산과 에틸아세테이트를 이용하여 칼럼크로마토그라피 방법으로 분리하여 4-페닐-2-(티오펜-2-일)퀴놀린을 얻었다(2.5 g, 수율: 77 %). To a three-neck flask was added 1- (thiophen-2-yl) ethanone (1.43 g, 11.3 mmol), 2- aminobenzophenone (2.46 g, 12.5 mmol), diphenyl phosphate 13.6 mmol) and metacresol (m-cresol, 8.0 mL) were added, and the mixture was stirred at room temperature for 20 minutes in a nitrogen atmosphere, and then refluxed for 12 hours. After cooling the three-necked flask to room temperature, methylene chloride (60 mL) and a 10% aqueous solution of sodium hydroxide (NaOH) were added, and the organic layer was separated. The obtained organic layer was washed with distilled water several times, dried over magnesium sulfate, and then separated by column chromatography using hexane and ethyl acetate to obtain 4-phenyl-2- (thiophen-2-yl) quinoline , Yield: 77%).

1H NMR (CDCl3) δ (ppm): 7.41-7.47 (m, 2H), 7.08-7.19 (m, 3H), 6.83-6.95 (m, 2H), 3.89-3.84 (t, J=7.8Hz, 2H), 2.58 (s, 3H), 1.82 (m, 2H), 1.25 (m, 4H), 0.98 (t, J=6.6Hz, 3H); 13C NMR (CDCl3) δ (ppm): 199.8, 144.9, 144.8, 136.1, 132.1, 132.0, 128.2, 122.7, 119.7, 118.9, 47.4, 31.5, 29.3, 27.5, 27.0, 22.7, 14.1 1 H NMR (CDCl 3) δ (ppm): 7.41-7.47 (m, 2H), 7.08-7.19 (m, 3H), 6.83-6.95 (m, 2H), 3.89-3.84 (t, J = 7.8Hz, 2H), 2.58 (s, 3H), 1.82 (m, 2H), 1.25 (m, 4H), 0.98 (t, J = 6.6Hz, 3H); 13 C NMR (CDCl 3) δ (ppm): 199.8, 144.9, 144.8, 136.1, 132.1, 132.0, 128.2, 122.7, 119.7, 118.9, 47.4, 31.5, 29.3, 27.5, 27.0, 22.7, 14.1

염소-Goat- 가교화Crosslinking 이합체의Dimer 제조 Produce

질소 분위기하에서 4-페닐-2-(티오펜-2-일)퀴놀린 (5 g, 17.40 mmol)과 이리듐클로라이드수화물 (IrCl3 3H2O) (2.08 g, 6.96 mmol)을 2-에톡시에탄올과 증류수 (80 mL, 3:1 v/v)에 녹인 용액을 140℃에서 24시간동안 교반하였다. 이어서 교반된 용액을 상온으로 냉각시킨 후, 생성된 노란색 고체를 여과하고 물-에탄올(3:1)로 잘 세척하여 원하는 생성물인 염소-가교화 이합체를 얻었다(3.36 g, 수율: 60%).
Phenyl-2- (thiophen-2-yl) quinoline (5 g, 17.40 mmol) and iridium chloride hydrate (IrCl 3 3H 2 O) (2.08 g, 6.96 mmol) in 2-ethoxyethanol and distilled water (80 mL, 3: 1 v / v) was stirred at 140 ° C for 24 hours. After cooling the stirred solution to room temperature, the resulting yellow solid was filtered and washed well with water-ethanol (3: 1) to obtain the desired product, chlorine-crosslinked dimer (3.36 g, yield: 60%).

[[ 실시예Example 1]  One] 4-4- 페닐Phenyl -2-(티오펜-2-일)퀴놀린 -2- (thiophen-2-yl) quinoline 주리간드와Primary ligand 4- 4- 클로로피콜리닉산의Chloropicolic acid 보조리간드를Secondary ligand 갖는 이리듐 착화합물{( Having iridium complex ({ ThTh -- PQPQ )) 22 Ir(4-Ir (4- ClCl -- picpic )}의 합성)}

Figure 112014018388164-pat00014
Figure 112014018388164-pat00014

염소-가교화 이합체 (2.3 g, 1.44 mmol), 4-클로로피콜리닉산 (0.68 g, 4.31 mmol), K2CO3 (1.99 g, 14.4 mmol)에 2-에톡시에탄올 (20 mL)를 가하여 8시간 환류하였다. 환류시킨 용액을 상온으로 냉각시킨 뒤 생성된 고체를 여과하고 물-에탄올(3:1)로 잘 세척하여 보조리간드로 4-클로로피콜리닉산이 도입된 이리듐 착화합물을 얻었다(0.84g, 수율: 63%). 이하, 본 실시예를 통하여 얻어진 이리듐 착화합물은 "(Th-PQ)2Ir(4-Cl-pic)"로 약칭한다. 본 실시예에 따라 얻어진 이리듐 착화합물의 NMR 결과가 하기에 표시되어 있다.2-ethoxyethanol (20 mL) was added to a chlorine-crosslinked dimer (2.3 g, 1.44 mmol), 4-chloropicolinic acid (0.68 g, 4.31 mmol) and K 2 CO 3 (1.99 g, 14.4 mmol) And refluxed for 8 hours. After cooling the refluxed solution to room temperature, the resulting solid was filtered and washed with water-ethanol (3: 1) to obtain an iridium complex having 4-chloropicolinic acid introduced as an auxiliary ligand (0.84 g, yield: 63 %). Hereinafter, the iridium complex obtained through this embodiment is abbreviated as "(Th-PQ) 2 Ir (4-Cl-pic)". NMR results of iridium complexes obtained according to this example are shown below.

1H NMR (300 MHz, CDCl3):δ (ppm) 8.73-8.70 (d, 1H), 7.96 (s, 1H), 7.85-7.83 (d, 1H), 7.75-7.72 (d, 2H), 7.67-7.63 (m, 3H), 7.61-7.55 (m, 10H), 7.39-7.33 (m, 3H), 7.22-7.15 (m, 3H), 6.96-6.95 (m, 1H), 6.66-6.64 (m, 1H), 6.19-6.17 (m,1H); 13C NMR (300 MHz, CDCl3):δ (ppm) 171.8, 166.6, 165.2, 154.38, 152.91, 152.82, 151.57, 149.80, 148.96, 147.64, 146.51, 141.52, 139.29, 137.40, 137.36, 134.79,133.5, 132.20, 130.99, 130.09, 130.01, 129.87, 129.27, 129.13, 128.98, 128.34, 128.27, 126.52, 126.36, 125.88, 125.68, 124.94, 124.79, 117.98, 116.9; Calcd for C44H27ClIrN3O2S2: C,57.35; H,2.95; N,4.56. Found: C,57.24; H,2.82; N,4.52. HRESI-MS [M+H]+:m/z found 921.4926, calcd for 921.49.
 1 H NMR (300 MHz, CDCl 3): δ (ppm) 8.73-8.70 (d, 1H), 7.96 (s, 1H), 7.85-7.83 (d, 1H), 7.75-7.72 (d, 2H), 7.67 (M, 3H), 6.96-6.95 (m, 1H), 6.66-6.64 (m, 3H), 7.96-7.55 1H), 6.19-6.17 (m, 1 H); 13 C NMR (300 MHz, CDCl 3): δ (ppm) 171.8, 166.6, 165.2, 154.38, 152.91, 152.82, 151.57, 149.80, 148.96, 147.64, 146.51, 141.52, 139.29, 137.40, 137.36, 134.79,133.5, 132.20 , 130.99, 130.09, 130.01, 129.87, 129.27, 129.13, 128.98, 128.34, 128.27, 126.52, 126.36, 125.88, 125.68, 124.94, 124.79, 117.98, 116.9; Calcd for C 44 H 27 ClIrN 3 O 2 S 2 : C, 57.35; H, 2.95; N, 4.56. Found: C, 57.24; H, 2.82; N, 4.52. HRESI-MS [M + H] < + >: m / z found 921.4926, calcd for 921.49.

[[ 실시예Example 2] 4- 2] 4- 페닐Phenyl -2-(티오펜-2-일)퀴놀린 -2- (thiophen-2-yl) quinoline 주리간드와Primary ligand 4- 4- 옥사디아졸피콜리닉Oxadiazolepolycinic 산을 Mountain 보조리간드를Secondary ligand 갖는 이리듐 착화합물{( Having iridium complex ({ ThTh -- PQPQ )) 22 Ir(4-Ir (4- OXDOXD -- picpic )}의 합성)}

Figure 112014018388164-pat00015
Figure 112014018388164-pat00015

실시예 1에서 합성되어진 이리듐 착화합물{(Th-PQ)2Ir(4-Cl-pic)} (1g, 0.57 mmol)과 4-(5-페닐-1,3,4-옥사디아졸-2-일)페놀 (1g,0.57mmol), 그리고 K2CO3 (0.60 g, 5.7 mmol)을 DMF (10 mL)에 녹인 후 80℃에서 질소 분위기에서 12시간 환류시켰다. 반응이 종료된 후 반응혼합물을 냉각시킨 후 물에 넣은 후 메틸렌클로라이드로 추출을 하고 무수 MgSO4로 수분을 제거한 후 에틸아세테이트:메틸렌클로라이드:헥산 (3:5:5, v/v/v) 비율로 컬럼크로마토그래피로 분리를 하여 (Th-PQ)2Ir(4-OXD-pic)을 얻었다(0.36 g, 수율: 59%). 본 실시예에 따라 얻어진 이리듐 착화합물의 NMR 결과가 하기에 표시되어 있다.(Th-PQ) 2 Ir (4-Cl-pic)} (1 g, 0.57 mmol) synthesized in Example 1 and 4- (5-phenyl-1,3,4-oxadiazol- Phenol (1 g, 0.57 mmol) and K 2 CO 3 (0.60 g, 5.7 mmol) were dissolved in DMF (10 mL) and refluxed in a nitrogen atmosphere at 80 ° C. for 12 hours. After the reaction was completed, the reaction mixture was cooled, and then water was added thereto. The mixture was extracted with methylene chloride, and water was removed by using anhydrous MgSO 4. The ethyl acetate: methylene chloride: hexane (3: 5: 5, v / To obtain (Th-PQ) 2 Ir (4-OXD-pic) (0.36 g, yield: 59%). NMR results of iridium complexes obtained according to this example are shown below.

1H NMR (300 MHz, CDCl3):δ(ppm) 8.80-8.77 (d, 1H), 8.17-8.15 (m, 4H), 7.87-7.85 (d, 1H), 7.81-7.77 (m, 3H), 7.71 (s, 1H), 7.65-7.57 (m, 16H), 7.41-7.36 (m, 3H), 7.19-7.17 (m, 3H), 7.07-7.02 (m, 2H), 6.70-6.69 (d, 1H), 6.21-6.19 (d,1H); 13C NMR (300 MHz, CDCl3):δ(ppm)171.81, 166.86, 165.55, 155.96, 153.57, 151.40, 150.04, 149.05, 139.25, 137.49, 133.62, 132.11, 130.94, 129.88, 129.55, 129.36, 129.03, 128.98, 127.24, 126.63, 126.41, 125.76, 124.93, 124.02, 122.12, 121.69, 115.24; IR(NaCl cell, cm-1):3057, 2355, 1652, 1596, 1539, 1495, 1452, 1425, 1325, 1290, 1242, 1203, 885, 846, 767, 732, 702, 584; Calcd for C58H36IrN5O4S2: C,62.02; H,3.23; N,6.23. Found: C,62.01; H,3.21; N,6.20. HRESI-MS [M+H]+:m/z found 1123.2761, calcd for 1123.27.
 1 H NMR (300 MHz, CDCl 3 ):? (Ppm) 8.80-8.77 (d, 1H), 8.17-8.15 (m, 4H), 7.87-7.85 , 7.71 (s, 1H), 7.65-7.57 (m, 16H), 7.41-7.36 (m, 3H), 7.19-7.17 (m, 3H), 7.07-7.02 1H), 6.21-6.19 (d, 1H); 13 C NMR (300 MHz, CDCl 3): δ (ppm) 171.81, 166.86, 165.55, 155.96, 153.57, 151.40, 150.04, 149.05, 139.25, 137.49, 133.62, 132.11, 130.94, 129.88, 129.55, 129.36, 129.03, 128.98 , 127.24, 126.63, 126.41, 125.76, 124.93, 124.02, 122.12, 121.69, 115.24; IR (NaCl cell, cm -1 ): 3057, 2355, 1652, 1596, 1539, 1495, 1452, 1425, 1325, 1290, 1242, 1203, 885, 846, 767, 732, 702, 584; Calcd for C 58 H 36 IrN 5 O 4 S 2 : C, 62.02; H, 3.23; N, 6.23. Found: C, 62.01; H, 3.21; N, 6.20. HRESI-MS [M + H] < + >: m / z found 1123.2761, Calcd for 1123.27.

[[ 실시예Example 3]  3] 이리듐(Iridium ( IIIIII )착화합물의 흡수스펙트럼 측정) Measurement of absorption spectrum of complex

본 실시예에서는 상기 실시예 2의 과정을 통하여 각각 합성된 이리듐 착화합물인 (Th-PQ)2Ir(4-OXD-pic)의 발광재료를 클로로포름에 용해시킨 상태에서 Shimadzu UV-3100 spectrometer를 사용하여 UV-visible 흡수스펙트럼을 측정하였다. In this example, the light-emitting material of the iridium complex (Th-PQ) 2 Ir (4-OXD-pic) synthesized through the procedure of Example 2 was dissolved in chloroform and irradiated using a Shimadzu UV-3100 spectrometer UV-visible absorption spectra were measured.

도 3은 상기 실시예 2에서 합성된 이리듐 착화합물인 (Th-PQ)2Ir(4-OXD-pic) 발광재료에 대한 UV-visible 흡수 스펙트럼 측정 결과를 도시한 그래프이다. 본 발명에 따라 합성된 이리듐 착화합물의 UV 흡수 피크를 살펴보면, 약 400 ㎚ 보다 단파장에서는 페닐퀴놀린과 티오펜 유도체의 전이현상이 일어나며, 보조리간드가 도입된 (Th-PQ)2Ir(4-OXD-pic)의 경우 장파장 약 492 ㎚에서 단일항과 삼중항의 중심금속-리간드간의 전하전달 상태가 일어남을 알 수 있다.
FIG. 3 is a graph showing the UV-visible absorption spectrum measurement results of the iridium complex (Th-PQ) 2 Ir (4-OXD-pic) light emitting material synthesized in Example 2 above. The UV absorption peaks of the iridium complexes synthesized according to the present invention show transition of phenyquinoline and thiophene derivatives at shorter wavelengths than about 400 nm. The (Th-PQ) 2 Ir (4-OXD- pic), the charge transfer state between the single metal and the center metal - ligand of triplet occurs at about 492 ㎚ long wavelength.

[[ 실시예Example 4]  4] 이리듐 착화합물의 용액 상태에서의 In the solution state of the iridium complex photoluminescence광화물 ( ( PLPL ) 측정 및 OLED 소자 특성) And OLED device characteristics

본 실시예에서는 상기 실시예 2에서 합성된 발광재료인 (Th-PQ)2Ir(4-OXD-pic)을 클로로포름에 용해시킨 상태에서 Hitachi F-4500으로 PL을 측정하였다. 각각의 이리듐계 발광재료에서 측정된 UV 최대 흡수파장을 여기파장으로 하여 PL을 측정하였으며, 도 4는 상기 실시예 2에서 합성된 보조리간드가 도입된 (Th-PQ)2Ir(4-OXD-pic)의 경우 발광재료에 대한 PL 측정 결과를 612 nm에서 최대 발광 피크가 형성되며 순수한 적색의 발광색을 나타냄을 알 수 있다.In this example, PL was measured with Hitachi F-4500 in a state in which (Th-PQ) 2 Ir (4-OXD-pic) which is the light emitting material synthesized in Example 2 was dissolved in chloroform. PL was measured using the UV absorption maximum wavelength measured in each iridium-based light emitting material as an excitation wavelength. FIG. 4 is a graph showing PL spectra of (Th-PQ) 2 Ir (4-OXD- pic), the PL measurement results for the light emitting material show that the maximum emission peak is formed at 612 nm and that the emission color is pure red.

상기 실시예 2에서 합성된 이리듐 착화합물인 (Th-PQ)2Ir(4-OXD-pic)을 이용하여 ITO/PEDOT:PSS/TCTA:TPBi:이리듐착화합물nm/PmPyPB/LiF/Al 형태의 OLED 소자를 제작하여 특성을 측정한 결과 도 5에서와 같이 EL 스펙트럼의 경우 625 nm에서 나타나고 있으며 색좌표는 (0.675, 0.323)로 매우 우수함을 알 수 있다.PEDOT: PSS / TCTA: TPBi: iridium complex nm / PmPyPB / LiF / Al type OLED device using the iridium complex (Th-PQ) 2 Ir (4-OXD-pic) synthesized in Example 2 As shown in FIG. 5, the EL spectra were obtained at 625 nm and the color coordinates (0.675, 0.323) were excellent.

선행문헌의 Ir(btp)2(acac)은 약 620 ㎚에서 최대 발광, 675 nm에서 발광피크를 나타내는 것에 비해 본 발명의 실시예 화합물들은 625 nm에서 최대의 발광피크가 형성되어 적색 발광특성 및 색순도에 있어서 더 향상되었다는 점을 확인 할 수 있었다.While Ir (btp) 2 (acac) of the prior art shows maximum emission at 620 nm and emission peak at 675 nm, the compounds of the present invention have maximum emission peak at 625 nm, Which is a further improvement over the other.

도 6 및 도 7은 각각 본 발명의 실시예 2에서 합성된 이리듐 착화합물인 (Th-PQ)2Ir(4-OXD-pic) 및 하기 구조의 이리듐 착화합물 (Th-PQ)2Ir(pic)의 전류밀도-전압-휘도 특성 및 휘도에 따른 외부 양자효율을 나타내는 도면으로, 이리듐 착화합물의 주리간드가 동일하고 보조리간드인 피콜리닉산의 4번 위치에 치환체체의 도입 유무에 따른 전류밀도-전압-휘도 특성 및 휘도에 따른 외부 양자효율을 각각 보여준다.6 and 7 are graphs showing the relationship between the iridium complex (Th-PQ) 2 Ir (4-OXD-pic) synthesized in Example 2 of the present invention and the iridium complex (Th-PQ) 2 Ir FIG. 3 is a graph showing the external quantum efficiency according to the current density-voltage-luminance characteristic and the luminance. FIG. 4 shows the current density-voltage-voltage characteristic of the iridium complex with the same main ligand and the presence of the substituent at the 4th position of the picolinic acid, And the external quantum efficiency according to the luminance characteristic and the luminance, respectively.

Figure 112014018388164-pat00016
Figure 112014018388164-pat00016

도 6으로부터 본 발명의 실시예 2에서 합성된 이리듐 착화합물 (Th-PQ)2Ir(4-OXD-pic)의 구동전압은 약 6V 정도이며, 최대 휘도는 1350 cd/m2로, 동일한 구조의 이리듐 착화합물에서 보조리간드인 피콜리닉산의 4번 위치에 수소 이외의 치환체가 도입되는 경우 구동전압이 낮아지는 것을 알 수 있었다. The driving voltage of 2 Ir (4-OXD-pic ) the iridium complex (Th-PQ) synthesized in Example 2 of the present invention; FIG. 6 is approximately 6V, the maximum luminance to 1350 cd / m 2, the same structure It was found that the driving voltage was lowered when a substituent other than hydrogen was introduced at the 4th position of the picolinic acid as an auxiliary ligand in the iridium complex.

도 7로부터 본 발명의 실시예 2에서 합성된 이리듐 착화합물 (Th-PQ)2Ir(4-OXD-pic)의 최대 외부 양자효율이 20.59%인 반면, 보조리간드인 피콜리닉산의 4번 위치에 수소만 치환된 이리듐 착화합물 (Th-PQ)2Ir(pic)의 최대 외부 양자효율은 5.92%로, 동일한 구조의 이리듐 착화합물에서 보조리간드인 피콜리닉산의 4번 위치에 수소 이외의 치환체가 도입되는 경우 최대 외부 양자효율 특성이 매우 우수함을 알 수 있었다. 7 shows that the maximum external quantum efficiency of the iridium complex (Th-PQ) 2 Ir (4-OXD-pic) synthesized in Example 2 of the present invention is 20.59%, while the maximum external quantum efficiency of the pyridinium complex The maximum external quantum efficiency of the hydrogen-only substituted iridium complex (Th-PQ) 2 Ir (pic) was 5.92%, and the substituent other than hydrogen was introduced at position 4 of the picolinic acid as an auxiliary ligand in the iridium complex of the same structure It was found that the maximum external quantum efficiency characteristic was excellent.

비교예인 Ir(btp)2(acac)이 도입된 ITO/NPD/CBP:Ir(btp)2(acac)/BCP/Alq3/ MgAg/Ag 형태의 OLED 소자를 제작하여 특성을 측정한 결과 도 8에서와 같이 최대 외부 양자효율이 6%임을 알 수 있다.
(Btp) 2 (acac) / BCP / Alq 3 / MgAg / Ag type organic EL device having a comparative example of Ir (btp) 2 (acac) The maximum external quantum efficiency is 6% as shown in Fig.

<도면의 주요부분에 대한 부호의 설명>
1000, 2000 : 유기전계발광소자 1100, 2100 : 기판
1110, 2110 : 제 1 전극 2120 : 정공주입층
2130 : 정공전달층 1140, 2140 : 발광층
2150 : 전자전달층 2160 : 전자주입층
1170, 2170 : 제 2 전극Description of the Related Art
1000, 2000: organic electroluminescence device 1100, 2100: substrate
1110, 2110: First electrode 2120: Hole injection layer
2130: hole transport layer 1140, 2140: light emitting layer
2150: electron transport layer 2160: electron injection layer
1170, 2170: second electrode

Claims (9)

삭제delete 하기 화학식 1로 표시되는 이리듐(III) 착화합물.
[화학식 1]
Figure 112015089645259-pat00031

상기 화학식 1에서, Ar은 (C6-C20)아릴이며; Z는 S이며; R1은 수소이며; R2는
Figure 112015089645259-pat00019
이고; L1은 (C6-C20)아릴렌이고; Ar1는 (C6-C20)아릴이다.An iridium (III) complex represented by the following formula (1).
[Chemical Formula 1]
Figure 112015089645259-pat00031

In Formula 1, Ar is (C6-C20) aryl; Z is S; R 1 is hydrogen; R 2 is
Figure 112015089645259-pat00019
ego; L &lt; 1 &gt; is (C6-C20) arylene; Ar 1 is (C6-C20) aryl. 제 2항에 있어서,
상기 R2는
Figure 112015089645259-pat00020
또는
Figure 112015089645259-pat00021
인 이리듐(III)착화합물.3. The method of claim 2,
Wherein R &lt; 2 &
Figure 112015089645259-pat00020
or
Figure 112015089645259-pat00021
Iridium (III) complex. 제 2항에 있어서,
하기 화합물로부터 선택되는 것을 특징으로 하는 이리듐(III)착화합물.
Figure 112015089645259-pat00032
3. The method of claim 2,
An iridium (III) complex, characterized in that it is selected from the following compounds.
Figure 112015089645259-pat00032
 제 2항 내지 제 4항에서 선택되는 어느 한 항에 따른 이리듐(III) 착화합물을 발광층에 포함하는 유기전계발광소자.An organic electroluminescent device comprising an luminescent layer with an iridium (III) complex according to any one of claims 2 to 4. 제 5항에 있어서,
상기 유기전계발광소자는 제 1 전극과, 상기 제 1 전극과 대향적으로 형성된 제 2 전극을 포함하며, 상기 발광층은 상기 제 1 전극과 제 2 전극 사이에 적층되어 있는 것을 특징으로 하는 유기전계발광소자. 6. The method of claim 5,
Wherein the organic electroluminescent device comprises a first electrode and a second electrode opposed to the first electrode, and the light emitting layer is stacked between the first electrode and the second electrode. device. 제 6항에 있어서,
상기 제 1 전극과 발광층 사이로 정공주입층 및 정공전달층을, 상기 발광층과 제 2 전극 사이로 전자전달층 및 전자주입층을 더욱 포함하는 유기전계발광소자. The method according to claim 6,
A hole injecting layer and a hole transporting layer between the first electrode and the light emitting layer, and an electron transporting layer and an electron injecting layer between the light emitting layer and the second electrode. 제 5항에 있어서,
상기 이리듐(III)착화합물을 발광층의 도판트로 포함되는 것을 특징으로 하는 유기 전계발광소자.6. The method of claim 5,
Wherein the iridium (III) complex is included as a dopant of the light emitting layer. 제 8항에 있어서,
상기 이리듐(III)착화합물은 발광층 총량을 기준으로 3~20 중량% 의 농도로 포함되어 있는 것을 특징으로 하는 유기전계발광소자.9. The method of claim 8,
Wherein the iridium (III) complex is contained in an amount of 3 to 20% by weight based on the total weight of the light emitting layer.
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