KR102585105B1 - Novel compound and organic electroluminescent device comprising same - Google Patents

Novel compound and organic electroluminescent device comprising same Download PDF

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KR102585105B1
KR102585105B1 KR1020150172150A KR20150172150A KR102585105B1 KR 102585105 B1 KR102585105 B1 KR 102585105B1 KR 1020150172150 A KR1020150172150 A KR 1020150172150A KR 20150172150 A KR20150172150 A KR 20150172150A KR 102585105 B1 KR102585105 B1 KR 102585105B1
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deuterium
unsubstituted
compound
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KR20160068683A (en
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함호완
김봉기
김성훈
안현철
김희주
박민수
김동준
한정우
이형진
임동환
안자은
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주식회사 동진쎄미켐
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Abstract

본 발명의 신규한 화합물은 유기발광소자에 발광층, 전자주입층 또는 전자수송층에 적용가능하며, 본 발명의 신규한 화합물과 카바졸 유도체를 유기발광소자의 호스트로 같이 사용함으로써 엑시플렉시 파장을 적절히 조절하여 유기발광소자의 효율 및 수명을 극대화 시킬 수 있다.The novel compound of the present invention can be applied to the light-emitting layer, electron injection layer, or electron transport layer of an organic light-emitting device, and the exiplex wavelength can be appropriately adjusted by using the novel compound of the present invention and a carbazole derivative as a host of the organic light-emitting device. Thus, the efficiency and lifespan of the organic light emitting device can be maximized.

Description

신규한 화합물 및 이를 포함하는 유기발광소자 {NOVEL COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING SAME}Novel compounds and organic light-emitting devices containing them {NOVEL COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING SAME}

본 발명은 신규한 화합물 및 이를 포함하는 유기발광소자에 관한 것이다. 또한 본 발명은 상기 신규한 화합물과 카바졸 유도체를 호스트로 같이 사용함으로써 엑시플렉시 파장을 적절히 조절하여 효율 및 수명을 극대화 시킨 유기발광소자에 관한 것이다. The present invention relates to novel compounds and organic light-emitting devices containing them. In addition, the present invention relates to an organic light-emitting device that maximizes efficiency and lifespan by appropriately controlling the exiplex wavelength by using the novel compound and carbazole derivatives together as a host.

최근, 자체 발광형으로 저전압 구동이 가능한 유기발광소자는, 평판 표시소자의 주류인 액정디스플레이(LCD, liquid crystal display)에 비해, 시야각, 대조비 등이 우수하고 백라이트가 불필요하여 경량 및 박형이 가능하며 소비전력 측면에서도 유리하고 색 재현 범위가 넓어, 차세대 표시소자로서 주목을 받고 있다.Recently, organic light emitting devices that are self-luminous and can be driven at low voltage have superior viewing angles and contrast ratios compared to liquid crystal displays (LCDs), the mainstream flat display devices, and do not require a backlight, making them lightweight and thin. It is attracting attention as a next-generation display device because it is advantageous in terms of power consumption and has a wide color reproduction range.

유기발광소자에서 유기물 층으로 사용되는 재료는 크게 기능에 따라, 발광 재료, 정공주입 재료, 정공수송 재료, 전자수송 재료, 전자주입 재료 등으로 분류될 수 있다. Materials used as organic layers in organic light-emitting devices can be broadly classified into light-emitting materials, hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on their function.

상기 발광 재료는 분자량에 따라 고분자과 저분자로 분류될 수 있고, 발광 메커니즘에 따라 전자의 일중항 여기상태로부터 유래되는 형광 재료와 전자의 삼중항 여기상태로부터 유래되는 인광 재료로 분류될 수 있으며, 발광 재료는 발광 색에 따라 청색, 녹색, 적색 발광 재료와 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 재료로 구분될 수 있다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 물질로서 호스트/도판트 계를 사용할 수 있다. 그 원리는 발광층을 주로 구성하는 호스트보다 에너지 대역 간극이 작고 발광 효율이 우수한 도판트를 발광층에 소량 혼합하면, 호스트에서 발생한 엑시톤이 도판트로 수송되어 효율이 높은 빛을 내는 것이다. 이때 호스트의 파장이 도판트의 파장대로 이동하므로, 이용하는 도판트와 호스트의 종류에 따라 원하는 파장의 빛을 얻을 수 있다. The light-emitting materials can be classified into high molecules and low molecules depending on their molecular weight, and can be classified into fluorescent materials derived from the singlet excited state of electrons and phosphorescent materials derived from the triplet excited state of electrons, depending on the light-emitting mechanism. Depending on the color of the light, it can be divided into blue, green, and red light-emitting materials and yellow and orange light-emitting materials necessary to realize better natural colors. Additionally, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system can be used as a luminescent material. The principle is that when a small amount of dopant, which has a smaller energy band gap and higher luminous efficiency than the host that mainly constitutes the light-emitting layer, is mixed into the light-emitting layer, excitons generated in the host are transported to the dopant, producing highly efficient light. At this time, since the wavelength of the host moves to the wavelength of the dopant, light of the desired wavelength can be obtained depending on the type of dopant and host used.

현재까지 이러한 유기발광소자에 사용되는 물질로서 다양한 화합물들이 알려져 있으나, 이제까지 알려진 물질을 이용한 유기발광소자의 경우 높은 구동전압, 낮은 효율 및 짧은 수명으로 인해 실용화하는 데에 많은 어려움이 있었다. To date, various compounds are known as materials used in such organic light-emitting devices, but in the case of organic light-emitting devices using hitherto known materials, there have been many difficulties in commercializing them due to high driving voltage, low efficiency, and short lifespan.

또한 상기 전자수송 재료에는 많이 연구되었으나 보다 높은 구동전압, 낮은 효율 및 짧은 수명으로 인해 실용화하는 데에 많은 어려움이 있었다. In addition, although much research has been done on the above electron transport materials, there have been many difficulties in putting them into practical use due to higher driving voltage, low efficiency, and short lifespan.

따라서, 우수한 특성을 갖는 물질을 이용하여 저전압 구동, 고휘도 및 장수명을 갖는 유기발광소자를 개발하려는 노력이 지속되어 왔다. Therefore, efforts have been made to develop organic light-emitting devices with low voltage operation, high brightness, and long lifespan using materials with excellent properties.

상기와 같은 문제점을 해결하기 위해, 본 발명은 유기발광소자에 발광호스트 또는 전자주입 및 전자수송재료로 사용가능하며, 유기발광소자에 적용시 장수명, 고효율, 저전압, 높은 Tg, 박막 안정성을 확보할 수 있으며, 특히 엑시플렉스 형성 및 도판트로의 에너지 전이를 통한 유기발광소자의 효율 및 수명을 극대화 할 수 있는 화합물을 제공하는 것을 목적으로 한다.
In order to solve the above problems, the present invention can be used as a light-emitting host or electron injection and electron transport material in organic light-emitting devices, and when applied to organic light-emitting devices, it can secure long life, high efficiency, low voltage, high Tg, and thin film stability. In particular, the purpose is to provide a compound that can maximize the efficiency and lifespan of organic light-emitting devices through exciplex formation and energy transfer to dopant.

또한 본 발명은 상기 화합물을 포함하여 장수명, 고효율, 저전압, 높은 Tg, 박막 안정성을 가지며, 특히 엑시플렉스 형성 및 도판트로의 에너지 전이를 통한 효율 및 수명을 극대화 한 유기발광소자를 제공하는 것을 목적으로 한다.In addition, the present invention aims to provide an organic light-emitting device that includes the above compounds and has long lifespan, high efficiency, low voltage, high Tg, and thin film stability, and in particular maximizes efficiency and lifespan through exciplex formation and energy transfer to dopant. do.

상기 목적을 달성하기 위해 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다:To achieve the above object, the present invention provides a compound represented by the following formula (1):

[화학식 1][Formula 1]

상기 식에서,In the above equation,

X, Y, Z는 각각 독립적으로 N 또는 CR이며, X, Y, Z 중 적어도 2개는 N이고, X, Y 중 적어도 하나는 N이며, 여기서 R은 수소; 중수소; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -30의 알킬기, C2 -30의 알케닐기, C2 -30의 알키닐기, C1 -30의 알콕시기, C6 -30의 아릴옥시기, C6 -30의 아릴기, 또는 C2 -30의 헤테로아릴기로 치환되거나 치환되지 않은 C6 -50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -30의 알킬기, C2 -30의 알케닐기, C2 -30의 알키닐기, C1 -30의 알콕시기, C6 -30의 아릴옥시기, C6 -30의 아릴기, 또는 C2 -30의 헤테로아릴기로 치환되거나 치환되지 않은 C2-50의 헤테로아릴기이고,X, Y, and Z are each independently N or CR, at least two of X, Y, and Z are N, and at least one of X and Y is N, where R is hydrogen; heavy hydrogen; Deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group , C 1-30 alkoxy group, C 6-30 aryloxy group period, a C 6 -30 aryl group, or a C 6 -50 aryl group substituted or unsubstituted with a C 2 -30 heteroaryl group; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group , C 2-30 alkenyl group, C 2-30 alkynyl group , C 1-30 alkoxy group, C 6-30 aryl It is a C 2-50 heteroaryl group substituted or unsubstituted with an oxy group, a C 6 -30 aryl group, or a C 2 -30 heteroaryl group,

R11 및 R12는 각각 독립적으로 수소; 중수소; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1 -30의 알킬기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2 -30의 알케닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2 -30의 알키닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1 -30의 알콕시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6 -30의 아릴옥시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -30의 알킬기, C2 -30의 알케닐기, C2 -30의 알키닐기, C1 -30의 알콕시기, C6 -30의 아릴옥시기, C6 -30의 아릴기, 또는 C2 -30의 헤테로아릴기로 치환되거나 치환되지 않은 C6 -50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -30의 알킬기, C2 -30의 알케닐기, C2 -30의 알키닐기, C1 -30의 알콕시기, C6 -30의 아릴옥시기, C6 -30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C2 -50의 헤테로아릴기이며, R11 및 R12가 수소 또는 중수소인 경우 연결부위인 C는 N일 수 있으며,R 11 and R 12 are each independently hydrogen; heavy hydrogen; C 1-30 alkyl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group , or nitro group; C 2-30 alkenyl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, or nitro group; C 2-30 alkynyl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, or nitro group; C 1-30 alkoxy group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group , or nitro group; C 6-30 aryloxy group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, or nitro group; Deuterium , halogen, amino group, nitrile group , nitro group , C 1-30 alkyl group , C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group , C 6-30 aryloxy group period, a C 6 -30 aryl group, or a C 6 -50 aryl group substituted or unsubstituted with a C 2 -30 heteroaryl group; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group , C 2-30 alkenyl group, C 2-30 alkynyl group , C 1-30 alkoxy group, C 6-30 aryl It is a C 2 -50 heteroaryl group substituted or unsubstituted with an oxy group, a C 6 -30 aryl group, or a C 2 -30 heteroaryl group, and when R 11 and R 12 are hydrogen or deuterium, C is the linking site. can be N,

상기 화합물 내의 트리페닐렌 구조 내의 탄소와 결합된 수소는 각각 독립적으로 C2 -30의 헤테로아릴기로 치환되거나 치환되지 않은 C6 -50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -30의 알킬기, C2 -30의 알케닐기, C2 -30의 알키닐기, C1 -30의 알콕시기, C6 -30의 아릴옥시기, C6 -30의 아릴기, 또는 C2 -30의 헤테로아릴기로 치환될 수 있다.
The hydrogen bonded to carbon in the triphenylene structure in the compound is each independently a C 6 -50 aryl group substituted or unsubstituted with a C 2 -30 heteroaryl group; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group , C 2-30 alkenyl group, C 2-30 alkynyl group , C 1-30 alkoxy group, C 6-30 aryl It may be substituted with an oxy group, a C 6 -30 aryl group, or a C 2 -30 heteroaryl group.

또한, 본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기발광소자를 제공한다.Additionally, the present invention provides an organic light-emitting device containing the compound represented by Formula 1 above.

본 발명의 화합물과 상기 화합물을 적용한 유기발광소자는 다음의 특징을 가진다.The compounds of the present invention and organic light-emitting devices using the compounds have the following characteristics.

1. 화합물 내의 트리페닐렌 구조의 도입으로 전자 및 정공에 대한 내구성 우수하여 유기발광소자의 장수명 확보.1. The introduction of the triphenylene structure in the compound ensures long lifespan of the organic light emitting device by providing excellent durability against electrons and holes.

2. 그린인광호스트로 적합한 삼중항 에너지 유지하여 유기발광소자의 고효율 확보.2. High efficiency of organic light emitting devices is secured by maintaining triplet energy suitable as a green phosphorescent host.

3. 화합물 내에 헤테로아릴기 도입으로 전자주입 및 수송 용이함으로써 유기발광소자의 저전압 구동 및 고효율 확보.3. The introduction of a heteroaryl group in the compound facilitates electron injection and transport, thereby ensuring low-voltage operation and high efficiency of organic light-emitting devices.

4. 화합물 내 Fused ring으로 높은 Tg 형성을 가능하게 하고, 유기발광소자 구동시 박막 안정성을 향상시킴.4. The fused ring in the compound enables high Tg formation and improves thin film stability when driving an organic light emitting device.

5. 유기발광소자에 적용시 본 발명의 신규한 화합물(발광호스트 1)과 카바졸 유도체(발광호스트 2)를 이용하여, 전자주입 및 수송이 용이하게 하고, 저전압 구동, 고효율을 가능하게 함.5. When applied to organic light-emitting devices, the novel compound (light-emitting host 1) and carbazole derivative (light-emitting host 2) of the present invention are used to facilitate electron injection and transport, and enable low-voltage operation and high efficiency.

6. 유기발광소자에 적용시 본 발명의 신규한 화합물(발광호스트 1)과 카바졸 유도체(발광호스트 2)의 사용을 통하여 엑시플렉스 형성 및 도판트로의 에너지 전이를 통한 효율 극대화시켜, 고효율 장수명을 가능하게 함.6. When applied to organic light-emitting devices, efficiency is maximized through exciplex formation and energy transfer to dopant through the use of the novel compound (light-emitting host 1) and carbazole derivative (light-emitting host 2) of the present invention, resulting in high efficiency and long life. Make it possible.

도 1은 본 발명의 일 실시예에 따른 OLED의 단면을 개략적으로 도시한 것이다.
도면의 부호
10 : 기판
11 : 양극
12 : 정공주입층
13 : 정공수송층
14 : 발광층
15 : 전자전달층
16: 음극Figure 1 schematically shows a cross section of an OLED according to an embodiment of the present invention.
symbols in drawings
10: substrate
11: anode
12: hole injection layer
13: hole transport layer
14: light emitting layer
15: electron transport layer
16: cathode

본 발명의 화합물은 하기 화학식 1로 표시되는 것을 특징으로 한다.The compound of the present invention is characterized by being represented by the following formula (1).

[화학식 1][Formula 1]

상기 식에서,In the above equation,

X, Y, Z는 각각 독립적으로 N 또는 CR이며, X, Y, Z 중 적어도 2개는 N이고, X, Y 중 적어도 하나는 N이며, 여기서 R은 수소; 중수소; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -30의 알킬기, C2 -30의 알케닐기, C2 -30의 알키닐기, C1 -30의 알콕시기, C6 -30의 아릴옥시기, C6 -30의 아릴기, 또는 C2 -30의 헤테로아릴기로 치환되거나 치환되지 않은 C6 -50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -30의 알킬기, C2 -30의 알케닐기, C2 -30의 알키닐기, C1 -30의 알콕시기, C6 -30의 아릴옥시기, C6 -30의 아릴기, 또는 C2 -30의 헤테로아릴기로 치환되거나 치환되지 않은 C2-50의 헤테로아릴기이고, 구체적으로는 X 중 적어도 하나는 N이며, Y 중 적어도 하나는 N이며,X, Y, and Z are each independently N or CR, at least two of X, Y, and Z are N, and at least one of X and Y is N, where R is hydrogen; heavy hydrogen; Deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group , C 1-30 alkoxy group, C 6-30 aryloxy group period, a C 6 -30 aryl group, or a C 6 -50 aryl group substituted or unsubstituted with a C 2 -30 heteroaryl group; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group , C 2-30 alkenyl group, C 2-30 alkynyl group , C 1-30 alkoxy group, C 6-30 aryl It is a C 2-50 heteroaryl group substituted or unsubstituted with an oxy group, a C 6-30 aryl group, or a C 2-30 heteroaryl group, and specifically , at least one of X is N, and at least one of Y is N,

R11 및 R12는 각각 독립적으로 수소; 중수소; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1 -30의 알킬기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2 -30의 알케닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2 -30의 알키닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1 -30의 알콕시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6 -30의 아릴옥시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -30의 알킬기, C2 -30의 알케닐기, C2 -30의 알키닐기, C1 -30의 알콕시기, C6 -30의 아릴옥시기, C6 -30의 아릴기, 또는 C2 -30의 헤테로아릴기로 치환되거나 치환되지 않은 C6 -50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -30의 알킬기, C2 -30의 알케닐기, C2 -30의 알키닐기, C1 -30의 알콕시기, C6 -30의 아릴옥시기, C6 -30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C2 -50의 헤테로아릴기이며, R11 및 R12가 수소 또는 중수소인 경우 연결부위인 C는 N일 수 있으며,R 11 and R 12 are each independently hydrogen; heavy hydrogen; C 1-30 alkyl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group , or nitro group; C 2-30 alkenyl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, or nitro group; C 2-30 alkynyl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, or nitro group; C 1-30 alkoxy group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group , or nitro group; C 6-30 aryloxy group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, or nitro group; Deuterium , halogen, amino group, nitrile group , nitro group , C 1-30 alkyl group , C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group , C 6-30 aryloxy group period, a C 6 -30 aryl group, or a C 6 -50 aryl group substituted or unsubstituted with a C 2 -30 heteroaryl group; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group , C 6-30 aryl It is a C 2 -50 heteroaryl group substituted or unsubstituted with an oxy group, a C 6 -30 aryl group, or a C 2 -30 heteroaryl group, and when R 11 and R 12 are hydrogen or deuterium, C is the linking site. can be N,

상기 화합물 내의 트리페닐렌 구조 내의 탄소와 결합된 수소는 각각 독립적으로 C2 -30의 헤테로아릴기로 치환되거나 치환되지 않은 C6 -50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -30의 알킬기, C2 -30의 알케닐기, C2 -30의 알키닐기, C1 -30의 알콕시기, C6 -30의 아릴옥시기, C6 -30의 아릴기, 또는 C2 -30의 헤테로아릴기로 치환될 수 있다.
The hydrogen bonded to carbon in the triphenylene structure in the compound is each independently a C 6 -50 aryl group substituted or unsubstituted with a C 2 -30 heteroaryl group; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group , C 6-30 aryl It may be substituted with an oxy group, a C 6 -30 aryl group, or a C 2 -30 heteroaryl group.

본 발명에 있어서, 상기 화학식 1로 표시되는 화합물은 하기 화학식 1-1 내지 1-7로 표시되는 것 중 하나일 수 있다.In the present invention, the compound represented by Formula 1 may be one of those represented by the following Formulas 1-1 to 1-7.

[화학식 1-1][Formula 1-1]

[화학식 1-2][Formula 1-2]

[화학식 1-3][Formula 1-3]

[화학식 1-4][Formula 1-4]

[화학식 1-5][Formula 1-5]

[화학식 1-6][Formula 1-6]

[화학식 1-7][Formula 1-7]



상기 화학식들에서 X, Y, Z는 화학식 1에서 정의한 바와 같으며, A는 각각 독립적으로 N 또는 CR0이며, 여기서 R0는 각각 독립적으로 수소; 중수소; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1 -30의 알킬기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2 -30의 알케닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2 -30의 알키닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1 -30의 알콕시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6 -30의 아릴옥시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6 -30의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2 -30의 헤테로아릴기이며, In the above formulas , heavy hydrogen; C 1-30 alkyl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group , or nitro group; C 2-30 alkenyl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, or nitro group; C 2-30 alkynyl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, or nitro group; C 1-30 alkoxy group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group , or nitro group; C 6-30 aryloxy group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, or nitro group; C 6 -30 aryl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, or nitro group; or a C 2 -30 heteroaryl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, or nitro group,

상기 화합물 내의 트리페닐렌 구조 내의 탄소와 결합된 수소는 각각 독립적으로 C2 -30의 헤테로아릴기로 치환되거나 치환되지 않은 C6 -50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -30의 알킬기, C2 -30의 알케닐기, C2 -30의 알키닐기, C1 -30의 알콕시기, C6 -30의 아릴옥시기, C6 -30의 아릴기, 또는 C2 -30의 헤테로아릴기로 치환될 수 있다.
The hydrogen bonded to carbon in the triphenylene structure in the compound is each independently a C 6 -50 aryl group substituted or unsubstituted with a C 2 -30 heteroaryl group; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group , C 2-30 alkenyl group, C 2-30 alkynyl group , C 1-30 alkoxy group, C 6-30 aryl It may be substituted with an oxy group, a C 6 -30 aryl group, or a C 2 -30 heteroaryl group.

본 발명에 있어서, 상기 화학식 1로 표시되는 화합물의 구체적인 예는 다음과 같다:In the present invention, specific examples of the compound represented by Formula 1 are as follows:

, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,

, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,

본 발명에 따른 화학식 1의 화합물은 정공 및 전자 전달 특성이 우수하고, 발광효율이 우수하며, 고색순도, 고효율 및 장수명을 가져, 유기발광소자에 적용시 우수한 소자특성을 나타낼 수 있다. 또한 화학식 1의 화합물은 전자주입이 용이하며, 전자수송 특성이 우수하고, 유기발광소자의 전자주입층 또는 전자수송층에 적용시 우수한 저전압, 고효율, 높은 Tg로 인한 안정성 및 장수명을 가지게 할 수 있다.
The compound of Formula 1 according to the present invention has excellent hole and electron transport properties, excellent luminous efficiency, high color purity, high efficiency, and long lifespan, and can exhibit excellent device characteristics when applied to organic light-emitting devices. In addition, the compound of Formula 1 is easy to inject electrons, has excellent electron transport properties, and can have excellent low voltage, high efficiency, stability and long life due to high Tg when applied to the electron injection layer or electron transport layer of an organic light-emitting device.

또한 본 발명의 화합물은 하기 반응식 1로 표시되는 반응식을 통하여 제조될 수 있다:Additionally, the compounds of the present invention can be prepared through the reaction scheme shown in Scheme 1 below:

[반응식 1][Scheme 1]

상기 반응식에서 X, Y, Z, R11 및 R12는 화학식 1에서 정의한 바와 같다.
In the above reaction formula, X, Y, Z, R 11 and R 12 are as defined in Formula 1.

또한, 본 발명은 상기 화학식 1로 표시되는 화합물을 유기물층에 포함하는 유기발광소자를 제공한다. 이때, 본 발명의 화합물은 구체적으로는 발광호스트, 전자주입물질 또는 전자수송물질로 단독으로 사용되거나 또는 공지의 화합물과 함께 사용될 수 있다. 더욱 구체적으로는 본 발명의 화합물을 발광호스트로 사용하는 것이며, 이 때 하기 화학식 2로 표시되는 발광화합물(발광호스트 2)을 본 발명의 화학식 1로 표시되는 화합물(발광호스트 1)과 함께 발광호스트로 같이 사용하는 것이 좋다. Additionally, the present invention provides an organic light-emitting device including the compound represented by Formula 1 above in an organic material layer. At this time, the compound of the present invention can be used alone or in combination with known compounds as a light-emitting host, electron injection material, or electron transport material. More specifically, the compound of the present invention is used as a light-emitting host, and at this time, the light-emitting compound (light-emitting host 2) represented by the following formula (2) is used together with the compound (light-emitting host 1) represented by the formula (1) of the present invention as the light-emitting host. It is better to use it together.

[화학식 2][Formula 2]

상기 화학식 2에서 r1 내지 r8은 각각 독립적으로 수소; 중수소; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1 -30의 알킬기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2 -30의 알케닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알키닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1 -30의 알콕시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6 -30의 아릴옥시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -30의 알킬기, C2 -30의 알케닐기, C2 -30의 알키닐기, C1 -30의 알콕시기, C6 -30의 아릴옥시기, C6 -30의 아릴기, 또는 C2 -30의 헤테로아릴기로 치환되거나 치환되지 않은 C6 -50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -30의 알킬기, C2 -30의 알케닐기, C2 -30의 알키닐기, C1 -30의 알콕시기, C6 -30의 아릴옥시기, C6-30의 아릴기, 또는 C2 -30의 헤테로아릴기로 치환되거나 치환되지 않은 C2 -50의 헤테로아릴기이며,In Formula 2, r 1 to r 8 are each independently hydrogen; heavy hydrogen; C 1-30 alkyl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group , or nitro group; C 2-30 alkenyl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, or nitro group; C 2-30 alkynyl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, or nitro group; C 1-30 alkoxy group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group , or nitro group; C 6-30 aryloxy group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, or nitro group; Deuterium , halogen, amino group, nitrile group , nitro group , C 1-30 alkyl group , C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group , C 6-30 aryloxy group period, a C 6 -30 aryl group, or a C 6 -50 aryl group substituted or unsubstituted with a C 2 -30 heteroaryl group; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group , C 6-30 aryl It is a C 2-50 heteroaryl group substituted or unsubstituted with an oxy group, a C 6-30 aryl group, or a C 2-30 heteroaryl group,

Ar은 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -30의 알킬기, C2 -30의 알케닐기, C2 -30의 알키닐기, C1 -30의 알콕시기, C6 -30의 아릴옥시기, C6 -30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은C6 -50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1 -30의 알킬기, C2 -30의 알케닐기, C2 -30의 알키닐기, C1 -30의 알콕시기, C6 -30의 아릴옥시기, C6 -30의 아릴기, 또는 C2 -30의 헤테로아릴기로 치환되거나 치환되지 않은 C2 -50의 헤테로아릴기이고,Ar is deuterium, halogen , amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group , C 6-30 An aryloxy group, a C 6 -30 aryl group, or a C 6 -50 aryl group substituted or unsubstituted with a C 2-30 heteroaryl group; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group , C 2-30 alkenyl group, C 2-30 alkynyl group , C 1-30 alkoxy group, C 6-30 aryl It is a C 2 -50 heteroaryl group substituted or unsubstituted with an oxy group, a C 6 -30 aryl group, or a C 2 -30 heteroaryl group,

m은 1 내지 4의 정수이며, m is an integer from 1 to 4,

m이 2내지 4일 때, Ar 및 r1~r8은 서로 연결될 수 있다.
When m is 2 to 4, Ar and r 1 to r 8 may be connected to each other.

구체적으로 상기 화학식 2의 화합물은 하기 화학식 2-1 내지 2-7로 표시되는 화합물 중 어느 하나인 것이 좋다.Specifically, the compound of Formula 2 is preferably any one of the compounds represented by the following Formulas 2-1 to 2-7.

[화학식 2-1][Formula 2-1]

[화학식 2-2][Formula 2-2]

[화학식 2-3][Formula 2-3]

[화학식 2-4][Formula 2-4]

[화학식 2-5][Formula 2-5]

[화학식 2-6] [Formula 2-6]

[화학식 2-7] [Formula 2-7]

상기 식들에서 Ar1, Ar2, Ar3, Ar4 , Ar5는 각각 독립적으로 상기 화학식 2의 Ar의 정의와 같으며, In the above formulas, Ar 1 , Ar 2 , Ar 3 , Ar 4 , and Ar 5 are each independently the same as the definition of Ar in Formula 2,

R1, R2, R3, R4는 상기 화학식 2의 r1 내지 r8의 정의와 같으며, R 1 , R 2 , R 3 , and R 4 are as defined for r 1 to r 8 in Formula 2 above,

a, b 각각 독립적으로 0 내지 3의 정수이다.
a and b are each independently an integer from 0 to 3.

화학식 2의 구체적인 화합물은 다음과 같다.Specific compounds of Formula 2 are as follows.

, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,

본 발명에서 상기 발광호스트 1 및 2를 통하여 형성된 엑시플렉스 발광파장이 400-650 nm로 형성하는 것이 가능하며, 발광호스트 1 및 2의 선택에 의하여 400-530 nm의 엑시플렉스 파장을 형성하여 녹색유기발광소자에 사용할 수 있으며, 500-630 nm의 엑시플렉스 파장을 형성하여 적색유기발광소자에 사용할 수 있다.In the present invention, it is possible to form an exciplex emission wavelength of 400-650 nm through the light-emitting hosts 1 and 2 , and by selecting light-emitting hosts 1 and 2, an exciplex wavelength of 400-530 nm can be formed to produce green organic matter. It can be used in light-emitting devices, and can be used in red organic light-emitting devices by forming an exciplex wavelength of 500-630 nm.

구체적으로 상기 발광호스트의 조합으로 형성된 엑시플렉스 파장이 발광층의 게스트인 도판트의 발광파장보다 단파장에서 형성되는 것이 좋다.
Specifically, it is better for the exciplex wavelength formed by the combination of the light-emitting host to be formed at a shorter wavelength than the emission wavelength of the dopant, which is a guest of the light-emitting layer.

또한 본 발명의 유기발광소자는 상기 화학식 1로 표시되는 화합물을 포함하는 1층 이상의 유기물층을 포함하는 것을 제외하고는 공지의 유기발광소자의 제조방법을 사용하여 유기발광소자를 제조할 수 있으며, 일예로 유기발광소자의 제조방법을 설명하면 다음과 같다.In addition, the organic light-emitting device of the present invention can be manufactured using a known manufacturing method of an organic light-emitting device, except that the organic light-emitting device includes one or more organic material layers containing the compound represented by Formula 1, for example The manufacturing method of the organic light emitting device is explained as follows.

상기 유기발광소자는 애노드(anode)와 캐소드(cathod) 사이에 정공주입층(HIL), 정공수송층(HTL), 발광층(EML), 전자수송층(ETL), 전자주입층(EIL) 등의 유기물층을 1 개 이상 포함할 수 있다.The organic light-emitting device has an organic material layer such as a hole injection layer (HIL), a hole transport layer (HTL), an emission layer (EML), an electron transport layer (ETL), and an electron injection layer (EIL) between an anode and a cathode. It may contain more than one.

먼저, 기판 상부에 높은 일함수를 갖는 애노드 전극용 물질을 증착시켜 애노드를 형성한다. 이때, 상기 기판은 통상의 유기발광소자에서 사용되는 기판을 사용할 수 있으며, 특히 기계적 강도, 열적 안정성, 투명성, 표면평활성, 취급용이성, 및 방수성이 우수한 유리 기판 또는 투명 플라스틱 기판을 사용하는 것이 좋다. 또한, 애노드 전극용 물질로는 투명하고 전도성이 우수한 산화인듐주석(ITO), 산화인듐아연(IZO), 산화주석(SnO2), 산화아연(ZnO) 등을 사용할 수 있다. 상기 애노드 전극용 물질은 통상의 애노드 형성방법에 의해 증착할 수 있으며, 구체적으로 증착법 또는 스퍼터링법에 의해 증착할 수 있다.First, an anode is formed by depositing a material for an anode electrode with a high work function on the top of the substrate. At this time, the substrate may be a substrate used in a typical organic light emitting device. In particular, it is preferred to use a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness. In addition, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity, can be used as materials for the anode electrode. The material for the anode electrode can be deposited using a normal anode forming method, and specifically, can be deposited using a vapor deposition method or a sputtering method.

그 다음, 상기 애노드 전극 상부에 정공주입층 물질을 진공증착법, 스핀코팅법, 캐스트법, LB(Langmuir-Blodgett)법 등과 같은 방법에 의해 형성할 수 있다. 상기 정공주입층 물질은 공지의 정공주입층 물질이 사용될 수 있으며, 일예로 미국특허 제4,356,429호에 개시된 구리 프탈로시아닌 등의 프탈로시아닌 화합물 또는 스타버스트형 아민 유도체류인 TCTA(4,4',4"-트리(N-카바졸릴)트리페닐아민), m-MTDATA(4,4',4"-트리스(3-메틸페닐아미노)트리페닐아민), m-MTDAPB(4,4',4"-트리스(3-메틸페닐아미노)페녹시벤젠), HI-406(N1,N1'-(비페닐-4,4'-디일)비스(N1-(나프탈렌-1-일)-N4,N4-디페닐벤젠-1,4-디아민) 등을 정공주입층 물질로 사용할 수 있다.Next, a hole injection layer material can be formed on the anode electrode by a method such as vacuum deposition, spin coating, casting, or Langmuir-Blodgett (LB) method. The hole injection layer material may be a known hole injection layer material, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429, or a starburst type amine derivative, TCTA (4,4',4"- tri(N-carbazolyl)triphenylamine), m-MTDATA(4,4',4"-tris(3-methylphenylamino)triphenylamine), m-MTDAPB(4,4',4"-tris( 3-methylphenylamino)phenoxybenzene), HI-406(N 1 ,N 1 '-(biphenyl-4,4'-diyl)bis(N 1 -(naphthalen-1-yl)-N 4 ,N 4 -Diphenylbenzene-1,4-diamine) etc. can be used as a hole injection layer material.

다음으로 상기 정공주입층 상부에 정공수송층 물질을 진공증착법, 스핀코팅법, 캐스트법, LB법 등과 같은 방법에 의해 형성할 수 있다.Next, a hole transport layer material can be formed on top of the hole injection layer by a method such as vacuum deposition, spin coating, casting, or LB method.

상기 정공수송층 물질은 공지의 정공수송층 물질이 혼합되어 사용될 수 있다. 구체적으로, 상기 공지의 정공수송층 물질로는 N-페닐카바졸, 폴리비닐카바졸 등의 카바졸 유도체, N,N'-비스(3-메틸페닐)-N,N'-디페닐-[1,1-비페닐]-4,4'-디아민(TPD), N.N'-디(나프탈렌-1-일)-N,N'-디페닐 벤지딘(α-NPD) 등의 방향족 축합환을 가지는 통상의 아민 유도체 등이 사용될 수 있다.The hole transport layer material may be used as a mixture of known hole transport layer materials. Specifically, the known hole transport layer materials include carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1, 1-biphenyl]-4,4'-diamine (TPD), N.N'-di(naphthalen-1-yl)-N,N'-diphenyl benzidine (α-NPD), etc. having an aromatic condensed ring Common amine derivatives, etc. may be used.

그 후, 상기 정공수송층 상부에 발광층 물질을 진공증착법, 스핀코팅법, 캐스트법, LB법 등과 같은 방법에 의해 형성할 수 있다. 상기 진공증착법에 의해 발광층을 형성하는 경우 그 증착조건은 사용하는 화합물에 따라 다르지만 일반적으로 정공주입층의 형성과 거의 동일한 조건 범위에서 선택하는 것이 좋다. Thereafter, a light-emitting layer material may be formed on the hole transport layer by a method such as vacuum deposition, spin coating, casting, or LB method. When forming a light-emitting layer by the vacuum deposition method, the deposition conditions vary depending on the compound used, but it is generally better to select conditions within the same range as those for forming the hole injection layer.

또한, 상기 발광층 재료는 공지의 호스트 또는 도펀트로 사용할 수 있으며, 구체적으로는 본 발명의 화학식 1로 표시되는 화합물을 호스트로 사용하는 것이 좋으며, 더욱 구체적으로는 본 발명의 화학식 1로 표시되는 화합물(발광호스트 1)과 화학식 2로 표시되는 화합물(발광호스트 2)을 동시에 사용하는 것이 좋으며, 상기 발광호스트로는 본 발명의 화학식 1로 표시되는 화합물(발광호스트 1)과 화학식 2로 표시되는 화합물(발광호스트 2)의 조합으로 형성된 엑시플렉스 파장이 발광층의 도판트의 발광파장보다 단파장에서 형성될 수 있도록 도판트 물질을 선택하여 사용하는 것이 좋다.In addition, the light emitting layer material can be used as a known host or dopant. Specifically, it is preferable to use the compound represented by Formula 1 of the present invention as a host, and more specifically, the compound represented by Formula 1 of the present invention ( It is recommended to use the light-emitting host 1) and the compound represented by Formula 2 (light-emitting host 2) at the same time, and the light-emitting host includes the compound represented by Formula 1 of the present invention (light-emitting host 1) and the compound represented by Formula 2 ( It is recommended to select and use a dopant material so that the exciplex wavelength formed by the combination of the light-emitting host 2) can be formed at a shorter wavelength than the emission wavelength of the dopant of the light-emitting layer.

사용 가능한 형광 도펀트로는 이데미츠사(Idemitsu사)에서 구입 가능한 IDE102 또는 IDE105, 또는 BD142(N6,N12-비스(3,4-디메틸페닐)-N6,N12-디메시틸크리센-6,12-디아민)를 사용할 수 있으며, 인광 도펀트로는 녹색 인광 도펀트 Ir(ppy)3(트리스(2-페닐피리딘) 이리듐), 청색 인광 도펀트인 F2Irpic(이리듐(Ⅲ) 비스[4,6-다이플루오로페닐)-피리디나토-N,C2'] 피콜린산염), UDC사의 적색 인광 도펀트 RD61 등이 공동 진공증착(도핑)될 수 있다. Usable fluorescent dopants include IDE102 or IDE105 available from Idemitsu, or BD142 (N 6 , N 12 -bis(3,4-dimethylphenyl)-N 6 , N 12 -dimethylchrysene- 6,12-diamine) can be used, and the green phosphorescent dopant Ir(ppy) 3 (tris(2-phenylpyridine) iridium) and the blue phosphorescent dopant F2Irpic (iridium(Ⅲ) bis[4,6-) can be used. Difluorophenyl)-pyridinato-N,C2'] picolinate), UDC's red phosphorescent dopant RD61, etc. can be co-vacuum deposited (doped).

또한 상기 정공수송층과 발광층 사이에는 발광보조층을 더욱 포함할 수 있으며, 발광보조층 재료로는 공지의 물질들이 사용될 수 있다.Additionally, a light-emitting auxiliary layer may be further included between the hole transport layer and the light-emitting layer, and known materials may be used as the light-emitting auxiliary layer material.

또한, 발광층에 삼중항 여기자 또는 정공이 전자수송층으로 확산되는 현상을 방지하기 위하여 정공억제재료(HBL)를 추가로 진공증착법 또는 스핀코팅법에 의해 적층시킬 수 있다. 이때 사용할 수 있는 정공억제물질은 특별히 제한되지는 않으나, 정공억제재료로 사용되고 있는 공지의 것에서 임의의 것을 선택해서 이용할 수 있다. 예를 들면, 옥사디아졸 유도체나 트리아졸 유도체, 페난트롤린 유도체, 또는 일본특개평 11-329734(A1)에 기재되어 있는 정공억제재료 등을 들 수 있으며, 대표적으로 Balq(비스(8-하이드록시-2-메틸퀴놀리놀나토)-알루미늄 비페녹사이드), 페난트롤린(phenanthrolines)계 화합물(예: UDC사 BCP(바쏘쿠프로인)) 등을 사용할 수 있다.Additionally, in order to prevent triplet excitons or holes from diffusing into the electron transport layer in the light emitting layer, a hole blocking material (HBL) may be additionally laminated by vacuum deposition or spin coating. The hole blocking material that can be used at this time is not particularly limited, but any material can be selected from known hole blocking materials and used. For example, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, or hole blocking materials described in Japanese Patent Application Laid-Open No. 11-329734 (A1), etc., representative examples include Balq (bis (8-hyde) Roxy-2-methylquinolinolnato)-aluminum biphenoxide), phenanthrolines-based compounds (e.g., UDC's BCP (bassocuproin)), etc. can be used.

상기와 같이 형성된 발광층 상부에는 전자수송층이 형성되는데, 이때 상기 전자수송층은 진공증착법, 스핀코팅법, 캐스트법 등의 방법으로 형성할 수 있다.An electron transport layer is formed on top of the light emitting layer formed as described above. At this time, the electron transport layer can be formed by a method such as vacuum deposition, spin coating, or casting.

상기 전자수송층 재료는 상기 화학식 1로 표시되는 화합물 또는 공지의 재료가 사용될 수 있으며, 공지의 재료의 예로는 퀴놀린 유도체, 특히 트리스(8-퀴놀리놀라토)알루미늄(Alq3), 또는 ET4(6,6'-(3,4-디메시틸-1,1-디메틸-1H-실올-2,5-디일)디-2,2'-비피리딘)을 사용할 수 있다. The electron transport layer material may be a compound represented by Formula 1 or a known material. Examples of the known material include quinoline derivatives, especially tris(8-quinolinolato)aluminum (Alq 3 ), or ET4(6). ,6'-(3,4-dimesityl-1,1-dimethyl-1H-silol-2,5-diyl)di-2,2'-bipyridine) can be used.

또한, 전자수송층 상부에 캐소드로부터 전자의 주입을 용이하게 하는 기능을 가지는 물질인 전자주입층(EIL)이 적층될 수 있으며, 전자주입층 물질로는 상기 화학식 1로 표시되는 화합물 또는 LiF, NaCl, CsF, Li2O, BaO 등의 물질을 이용할 수 있다.In addition, an electron injection layer (EIL), a material that has the function of facilitating injection of electrons from the cathode, may be laminated on the electron transport layer. The electron injection layer material may include a compound represented by Formula 1 above, LiF, NaCl, Materials such as CsF, Li 2 O, and BaO can be used.

마지막으로 전자수송층 또는 전자주입층 상부에 캐소드 형성용 금속을 진공증착법이나 스퍼터링법 등의 방법에 의해 형성하고 캐소드로 사용한다. 여기서 캐소드 형성용 금속으로는 낮은 일함수를 가지는 금속, 합금, 전기전도성 화합물, 및 이들의 혼합물을 사용할 수 있다. 구체적인 예로는 리튬(Li), 마그네슘(Mg), 알루미늄(Al), 알루미늄-리튬(Al-Li), 칼슘(Ca), 마그네슘-인듐(Mg-In), 마그네슘-은(Mg-Ag) 등이 있다. 또한, 전면 발광소자를 얻기 위하여 ITO, IZO를 사용한 투과형 캐소드를 사용할 수도 있다.Finally, a metal for forming a cathode is formed on the top of the electron transport layer or electron injection layer by a method such as vacuum deposition or sputtering and used as a cathode. Here, metals having a low work function, alloys, electrically conductive compounds, and mixtures thereof can be used as the metal for forming the cathode. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. There is. Additionally, a transmissive cathode using ITO or IZO can be used to obtain a front light emitting device.

본 발명의 유기발광소자는 애노드, 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층, 캐소드 구조의 유기발광소자 뿐만 아니라, 다양한 구조의 유기발광소자의 구조가 가능하며, 필요에 따라 1층 또는 2층의 중간층을 더 형성하는 것도 가능하다.The organic light emitting device of the present invention is capable of being an organic light emitting device having an anode, hole injection layer, hole transport layer, light emitting layer, electron transport layer, electron injection layer, and cathode structure, as well as an organic light emitting device of various structures, depending on need. It is also possible to further form a layer or an intermediate layer of two layers.

상기와 같이 본 발명에 따라 형성되는 각 유기물층의 두께는 요구되는 정도에 따라 조절할 수 있으며, 구체적으로는 10 내지 1,000 ㎚이며, 더욱 구체적으로는 20 내지 150 ㎚인 것이 좋다.As described above, the thickness of each organic layer formed according to the present invention can be adjusted according to the required degree, and is preferably 10 to 1,000 nm, and more specifically 20 to 150 nm.

또한 본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 유기물층의 두께를 분자 단위로 조절할 수 있기 때문에 표면이 균일하며, 형태안정성이 뛰어난 장점이 있다.
In addition, the present invention has the advantage that the organic material layer containing the compound represented by Formula 1 has a uniform surface and excellent morphological stability because the thickness of the organic material layer can be adjusted on a molecular basis.

본 발명의 유기발광소자는 전자 및 정공에 대한 내구성 우수하여 유기발광소자의 장수명, 저전압 구동 및 고효율의 확보가 가능하며, 박막 안정성이 우수하며, 본 발명의 신규한 화합물(발광호스트 1)과 카바졸 유도체(발광호스트 2)를 이용하여, 전자주입 및 수송이 용이하게 하고, 저전압 구동, 고효율을 가능하게 하며, 엑시플렉스 형성 및 도판트로의 에너지 전이를 통한 효율 극대화시켜, 고효율 장수명을 가능하게 할 수 있다.
The organic light emitting device of the present invention has excellent durability against electrons and holes, enabling long life, low voltage operation, and high efficiency of the organic light emitting device, excellent thin film stability, and the novel compound (light emitting host 1) of the present invention and carboxylic acid. Using a sol derivative (luminescent host 2), it facilitates electron injection and transport, enables low-voltage operation and high efficiency, and maximizes efficiency through exciplex formation and energy transfer to dopant, enabling high efficiency and long life. You can.

이하, 본 발명의 이해를 돕기 위하여 구체적인 실시예를 제시하나, 하기 실시예는 본 발명을 예시하는 것일 뿐 본 발명의 범위가 하기 실시예에 한정되는 것은 아니다.
Hereinafter, specific examples will be presented to aid understanding of the present invention. However, the following examples are merely illustrative of the present invention and the scope of the present invention is not limited to the following examples.

중간체 intermediate I1I1 의 합성synthesis of

[I1-1의 합성][Synthesis of I1-1]

둥근바닥플라스크에 triphenylen-2-ylboronic acid 20.0g, 1-bromo-3-iodobenzene 19.3g을 톨루엔 400ml에 녹이고 K2CO3(2M) 105ml와 Pd(PPh3)4 2.5g을 넣은 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결시켰다. 유기층을 MC로 추출하고 감압여과한 후 컬럼정제하여 중간체 I1-1 16.8g (수율 62%)를 얻었다.In a round bottom flask, 20.0 g of triphenylen-2-ylboronic acid and 19.3 g of 1-bromo-3-iodobenzene were dissolved in 400 ml of toluene, 105 ml of K 2 CO 3 (2M) and 2.5 g of Pd(PPh 3 ) 4 were added, and then refluxed and stirred. . The reaction was confirmed by TLC and the reaction was terminated after adding water. The organic layer was extracted with MC, filtered under reduced pressure, and purified by column to obtain 16.8 g of intermediate I1-1 (yield 62%).

[I1의 합성][Synthesis of I1]

상기 중간체 I1-1 16.5g, bis(pinacolato)diboron 14.2g, Pd(dppf)Cl2 0.15g, KOAc 12.7g을 1,4-Dioxane 450ml에 녹인 후 환류 교반하였다. TLC로 반응을 확인하고 유기층을 MC추출하고 컬럼정제하여 중간체 I1 15.2g (수율 82%)를 얻었다.
16.5 g of the intermediate I1-1, 14.2 g of bis(pinacolato)diboron, 0.15 g of Pd(dppf)Cl 2 and 12.7 g of KOAc were dissolved in 450 ml of 1,4-Dioxane and stirred under reflux. The reaction was confirmed by TLC, and the organic layer was extracted with MC and purified by column to obtain 15.2 g of intermediate I1 (yield 82%).

중간체 intermediate I2I2 의 합성synthesis of

[I2-1의 합성][Synthesis of I2-1]

둥근바닥플라스크에 상기 중간체 I1 15.0g, 3,5-dibromopyridine 8.25g을 톨루엔 300ml에 녹이고 K2CO3(2M) 50ml와 Pd(PPh3)4 1.2g을 넣은 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결시켰다. 유기층을 MC로 추출하고 감압여과한 후 컬럼정제하여 중간체 I2-1 8.66g (수율 54%)를 얻었다.In a round bottom flask, 15.0 g of the intermediate I1 and 8.25 g of 3,5-dibromopyridine were dissolved in 300 ml of toluene, 50 ml of K 2 CO 3 (2M) and 1.2 g of Pd(PPh 3 ) 4 were added, followed by refluxing and stirring. The reaction was confirmed by TLC and the reaction was terminated after adding water. The organic layer was extracted with MC, filtered under reduced pressure, and purified by column to obtain 8.66 g of intermediate I2-1 (yield 54%).

[I2의 합성][Synthesis of I2]

상기 중간체 I2-1 8.5g, bis(pinacolato)diboron 6.1g, Pd(dppf)Cl2 0.06g, KOAc 5.4g을 1,4-Dioxane 220ml에 녹인 후 환류 교반하였다. TLC로 반응을 확인하고 유기층을 MC추출하고 컬럼정제하여 중간체 I2 7.03g (수율 75%)를 얻었다.
8.5 g of the intermediate I2-1, 6.1 g of bis(pinacolato)diboron, 0.06 g of Pd(dppf)Cl 2 , and 5.4 g of KOAc were dissolved in 220 ml of 1,4-Dioxane and stirred under reflux. The reaction was confirmed by TLC, and the organic layer was extracted with MC and purified by column to obtain 7.03 g of intermediate I2 (yield 75%).

중간체 intermediate I3I3 의 합성synthesis of

상기 I1의 합성에서 1-bromo-3-iodobenzene 대신 2,4-dibromopyridine을 사용한 것을 제외하고는 I1의 합성방법을 준용하여 I3을 합성하였다.In the synthesis of I1, I3 was synthesized by following the method of synthesis of I1, except that 2,4-dibromopyridine was used instead of 1-bromo-3-iodobenzene.

중간체 intermediate I4I4 의 합성synthesis of

상기 I1의 합성에서 1-bromo-3-iodobenzene 대신 3,5-dibromopyridine 을 사용한 것을 제외하고는 I1의 합성방법을 준용하여 I4을 합성하였다.
I4 was synthesized by following the method of synthesis of I1, except that 3,5-dibromopyridine was used instead of 1-bromo-3-iodobenzene in the synthesis of I1.

중간체 intermediate I5I5 의 합성synthesis of

상기 I1의 합성에서 1-bromo-3-iodobenzene 대신 2-bromo-4-iodopyridine 을 사용한 것을 제외하고는 I1의 합성방법을 준용하여 I5을 합성하였다.
I5 was synthesized by following the method of synthesis of I1, except that 2-bromo-4-iodopyridine was used instead of 1-bromo-3-iodobenzene in the synthesis of I1.

중간체 intermediate I6I6 의 합성synthesis of

상기 I1의 합성에서 1-bromo-3-iodobenzene 대신 3,5-dibromo-1,1'-biphenyl 을 사용한 것을 제외하고는 I1의 합성방법을 준용하여 I6을 합성하였다.
I6 was synthesized by following the method of synthesis of I1, except that 3,5-dibromo-1,1'-biphenyl was used instead of 1-bromo-3-iodobenzene in the synthesis of I1.

중간체 intermediate I7I7 의 합성synthesis of

상기 I1의 합성에서 1-bromo-3-iodobenzene 대신 2-(3,5-dibromophenyl)pyridine 을 사용한 것을 제외하고는 I1의 합성방법을 준용하여 I6을 합성하였다.
I6 was synthesized by applying the method of synthesis of I1, except that 2-(3,5-dibromophenyl)pyridine was used instead of 1-bromo-3-iodobenzene in the synthesis of I1.

[[ 화학식1Formula 1 ]의 합성] synthesis

화합물 1-1Compound 1-1

둥근바닥플라스크에 상기 중간체 I3 5.0g, 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 4.95g을 톨루엔 100ml에 녹이고 K2CO3(2M) 18ml와 Pd(PPh3)4 0.4g을 넣은 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결시켰다. 유기층을 MC로 추출하고 감압여과한 후 재결정하여 화합물 1-1 4.69g (수율 66%)를 얻었다.In a round bottom flask, 5.0 g of the intermediate I3 and 4.95 g of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine were dissolved in 100 ml of toluene, and 18 ml of K 2 CO 3 (2M) and Pd(PPh) were dissolved in 100 ml of toluene. 3 ) After adding 0.4g of 4 , it was refluxed and stirred. The reaction was confirmed by TLC and the reaction was terminated after adding water. The organic layer was extracted with MC, filtered under reduced pressure, and recrystallized to obtain 4.69 g of Compound 1-1 (yield 66%).

m/z: 612.23 (100.0%), 613.23 (49.1%), 614.24 (11.2%), 615.24 (1.9%)
m/z: 612.23 (100.0%), 613.23 (49.1%), 614.24 (11.2%), 615.24 (1.9%)

화합물1Compound 1 -2-2

상기 화합물1-1과 같은 방법으로 중간체 I3 대신 중간체 I4를 이용하여 화합물 1-2를 합성하였다.(수율 60%)Compound 1-2 was synthesized in the same manner as Compound 1-1, using Intermediate I4 instead of Intermediate I3 (yield 60%).

m/z: 612.23 (100.0%), 613.23 (49.1%), 614.24 (11.2%), 615.24 (1.9%)
m/z: 612.23 (100.0%), 613.23 (49.1%), 614.24 (11.2%), 615.24 (1.9%)

화합물1Compound 1 -3-3

상기 화합물1-1과 같은 방법으로 중간체 I3 대신 중간체 I5를 이용하여 화합물 1-3을 합성하였다.(수율 64%)Compound 1-3 was synthesized in the same manner as Compound 1-1, using Intermediate I5 instead of Intermediate I3 (yield 64%).

m/z: 612.23 (100.0%), 613.23 (49.1%), 614.24 (11.2%), 615.24 (1.9%)
m/z: 612.23 (100.0%), 613.23 (49.1%), 614.24 (11.2%), 615.24 (1.9%)

화합물 1-4Compound 1-4

상기 화합물1-1과 같은 방법으로 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 4-(3-bromophenyl)-2,6-diphenylpyrimidine를 이용하여 화합물 1-4를 합성하였다.(수율 63%)Compound 1- was prepared in the same manner as Compound 1-1, using 4-(3-bromophenyl)-2,6-diphenylpyrimidine instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine. 4 was synthesized (yield 63%).

m/z: 611.24 (100.0%), 612.24 (49.0%), 613.24 (12.1%), 614.25 (1.8%), 612.23 (1.1%)
m/z: 611.24 (100.0%), 612.24 (49.0%), 613.24 (12.1%), 614.25 (1.8%), 612.23 (1.1%)

화합물 1-5Compound 1-5

상기 화합물1-1과 같은 방법으로 중간체 I3 대신 중간체 I4로 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 4-(3-bromophenyl)-2,6-diphenylpyrimidine 를 이용하여 화합물 1-5를 합성하였다.(수율 58%)In the same manner as Compound 1-1, replace intermediate I3 with intermediate I4 and replace 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine with 4-(3-bromophenyl)-2,6-diphenylpyrimidine. Compound 1-5 was synthesized using (yield 58%).

m/z: 611.24 (100.0%), 612.24 (49.0%), 613.24 (12.1%), 614.25 (1.8%), 612.23 (1.1%)
m/z: 611.24 (100.0%), 612.24 (49.0%), 613.24 (12.1%), 614.25 (1.8%), 612.23 (1.1%)

화합물 1-6Compound 1-6

상기 화합물1-1과 같은 방법으로 중간체 I3 대신 중간체 I5로 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 4-(3-bromophenyl)-2,6-diphenylpyrimidine 를 이용하여 화합물 1-5를 합성하였다.(수율 55%)In the same manner as Compound 1-1, use Intermediate I5 instead of Intermediate I3 and 4-(3-bromophenyl)-2,6-diphenylpyrimidine instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine. Compound 1-5 was synthesized using (yield 55%)

m/z: 611.24 (100.0%), 612.24 (49.0%), 613.24 (12.1%), 614.25 (1.8%), 612.23 (1.1%)
m/z: 611.24 (100.0%), 612.24 (49.0%), 613.24 (12.1%), 614.25 (1.8%), 612.23 (1.1%)

화합물 1-7Compound 1-7

상기 화합물1-1과 같은 방법으로 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 2-(3-bromophenyl)-4,6-diphenylpyrimidine 를 이용하여 화합물 1-7을 합성하였다.(수율 60%)Compound 1- was prepared in the same manner as Compound 1-1, using 2-(3-bromophenyl)-4,6-diphenylpyrimidine instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine. 7 was synthesized (yield 60%).

m/z: 611.24 (100.0%), 612.24 (49.0%), 613.24 (12.1%), 614.25 (1.8%), 612.23 (1.1%)
m/z: 611.24 (100.0%), 612.24 (49.0%), 613.24 (12.1%), 614.25 (1.8%), 612.23 (1.1%)

화합물 1-8Compound 1-8

상기 화합물1-1과 같은 방법으로 중간체 I3 대신 중간체 I4로 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 2-(3-bromophenyl)-4,6-diphenylpyrimidine를 이용하여 화합물 1-8을 합성하였다.(수율 63%)In the same manner as Compound 1-1, use Intermediate I4 instead of Intermediate I3 and 2-(3-bromophenyl)-4,6-diphenylpyrimidine instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine. Compound 1-8 was synthesized using (yield 63%).

m/z: 611.24 (100.0%), 612.24 (49.0%), 613.24 (12.1%), 614.25 (1.8%), 612.23 (1.1%)
m/z: 611.24 (100.0%), 612.24 (49.0%), 613.24 (12.1%), 614.25 (1.8%), 612.23 (1.1%)

화합물 1-9Compound 1-9

상기 화합물1-1과 같은 방법으로 중간체 I3 대신 중간체 I5로 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 2-(3-bromophenyl)-4,6-diphenylpyrimidine를 이용하여 화합물 1-9를 합성하였다.(수율 67%)In the same manner as Compound 1-1, use Intermediate I5 instead of Intermediate I3 and 2-(3-bromophenyl)-4,6-diphenylpyrimidine instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine. Compound 1-9 was synthesized using (yield 67%).

m/z: 611.24 (100.0%), 612.24 (49.0%), 613.24 (12.1%), 614.25 (1.8%), 612.23 (1.1%)
m/z: 611.24 (100.0%), 612.24 (49.0%), 613.24 (12.1%), 614.25 (1.8%), 612.23 (1.1%)

화합물 1-10Compound 1-10

상기 화합물1-1과 같은 방법으로 중간체 I3 대신 중간체 I2로 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4,6-diphenyl-1,3,5-triazine를 이용하여 화합물 1-10을 합성하였다.(수율 52%)In the same manner as Compound 1-1, use Intermediate I2 instead of Intermediate I3 and 2-chloro-4,6-diphenyl-1,3 instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine. Compound 1-10 was synthesized using 5-triazine (yield 52%).

m/z: 612.23 (100.0%), 613.23 (49.1%), 614.24 (11.2%), 615.24 (1.9%)
m/z: 612.23 (100.0%), 613.23 (49.1%), 614.24 (11.2%), 615.24 (1.9%)

화합물1Compound 1 -11-11

상기 화합물1-1과 같은 방법으로 중간체 I3 대신 중간체 I2로 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4,6-diphenylpyrimidine를 이용하여 화합물 1-11을 합성하였다.(수율 55%)In the same manner as Compound 1-1, using Intermediate I2 instead of Intermediate I3 and 2-chloro-4,6-diphenylpyrimidine instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine, a compound was prepared. 1-11 was synthesized (yield 55%).

m/z: 611.24 (100.0%), 612.24 (49.0%), 613.24 (12.1%), 614.25 (1.8%), 612.23 (1.1%)
m/z: 611.24 (100.0%), 612.24 (49.0%), 613.24 (12.1%), 614.25 (1.8%), 612.23 (1.1%)

화합물1Compound 1 -12-12

상기 화합물1-1과 같은 방법으로 중간체 I3 대신 중간체 I2로 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 4-chloro-2,6-diphenylpyrimidine를 이용하여 화합물 1-12를 합성하였다.(수율 50%)In the same manner as Compound 1-1 above, using Intermediate I2 instead of Intermediate I3 and 4-chloro-2,6-diphenylpyrimidine instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine, a compound was prepared. 1-12 were synthesized (yield 50%).

m/z: 611.24 (100.0%), 612.24 (49.0%), 613.24 (12.1%), 614.25 (1.8%), 612.23 (1.1%)m/z: 611.24 (100.0%), 612.24 (49.0%), 613.24 (12.1%), 614.25 (1.8%), 612.23 (1.1%)

화합물1Compound 1 -13-13

상기 화합물1-1과 같은 방법으로 중간체 I3 대신 중간체 I6로 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4,6-diphenyl-1,3,5-triazine를 이용하여 화합물 1-13을 합성하였다.(수율 56%)In the same manner as Compound 1-1, use Intermediate I6 instead of Intermediate I3 and 2-chloro-4,6-diphenyl-1,3 instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine. Compound 1-13 was synthesized using 5-triazine (yield 56%).

m/z: 611.24 (100.0%), 612.24 (49.0%), 613.24 (12.1%), 614.25 (1.8%), 612.23 (1.1%)
m/z: 611.24 (100.0%), 612.24 (49.0%), 613.24 (12.1%), 614.25 (1.8%), 612.23 (1.1%)

화합물1Compound 1 -14-14

상기 화합물1-1과 같은 방법으로 중간체 I3 대신 중간체 I7로 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4,6-diphenyl-1,3,5-triazine를 이용하여 화합물 1-14를 합성하였다.(수율 54%)In the same manner as Compound 1-1, use Intermediate I7 instead of Intermediate I3 and 2-chloro-4,6-diphenyl-1,3 instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine. Compound 1-14 was synthesized using 5-triazine (yield 54%).

m/z: 612.23 (100.0%), 613.23 (49.1%), 614.24 (11.2%), 615.24 (1.9%)
m/z: 612.23 (100.0%), 613.23 (49.1%), 614.24 (11.2%), 615.24 (1.9%)

화합물1Compound 1 -15-15

상기 화합물1-1과 같은 방법으로 중간체 I3 대신 중간체 I1로 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine를 이용하여 화합물 1-15를 합성하였다.(수율 50%)In the same manner as Compound 1-1, use Intermediate I1 instead of Intermediate I3 and 2-([1,1'-biphenyl]-3 instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine. Compound 1-15 was synthesized using -yl)-4-chloro-6-phenyl-1,3,5-triazine (yield 50%).

m/z: 611.24 (100.0%), 612.24 (49.0%), 613.24 (12.1%), 614.25 (1.8%), 612.23 (1.1%)
m/z: 611.24 (100.0%), 612.24 (49.0%), 613.24 (12.1%), 614.25 (1.8%), 612.23 (1.1%)

화합물1Compound 1 -16-16

상기 화합물1-1과 같은 방법으로 중간체 I3 대신 중간체 I1로 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-phenyl-6-(3-(pyridin-2-yl)phenyl)-1,3,5-triazine를 이용하여 화합물 1-16을 합성하였다.(수율 54%)In the same manner as Compound 1-1, use Intermediate I1 instead of Intermediate I3 and 2-chloro-4-phenyl-6-(3- instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine. Compound 1-16 was synthesized using (pyridin-2-yl)phenyl)-1,3,5-triazine (yield 54%).

m/z: 612.23 (100.0%), 613.23 (49.1%), 614.24 (11.2%), 615.24 (1.9%)
m/z: 612.23 (100.0%), 613.23 (49.1%), 614.24 (11.2%), 615.24 (1.9%)

화합물1Compound 1 -17-17

상기 화합물1-1과 같은 방법으로 중간체 I3 대신 중간체 I1로 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-phenyl-6-(3-(pyridin-3-yl)phenyl)pyrimidine를 이용하여 화합물 1-17을 합성하였다.(수율 52%)In the same manner as Compound 1-1, use Intermediate I1 instead of Intermediate I3 and 2-chloro-4-phenyl-6-(3- instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine. Compound 1-17 was synthesized using (pyridin-3-yl)phenyl)pyrimidine (yield 52%).

m/z: 611.24 (100.0%), 612.24 (49.0%), 613.24 (12.1%), 614.25 (1.8%), 612.23 (1.1%)
m/z: 611.24 (100.0%), 612.24 (49.0%), 613.24 (12.1%), 614.25 (1.8%), 612.23 (1.1%)

화합물 1-18Compound 1-18

상기 화합물1-1과 같은 방법으로 중간체 I3 대신 중간체 I1로 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-phenyl-6-(3-(pyridin-4-yl)phenyl)pyrimidine를 이용하여 화합물 1-18을 합성하였다.(수율 50%)In the same manner as Compound 1-1, use Intermediate I1 instead of Intermediate I3 and 2-chloro-4-phenyl-6-(3- instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine. Compound 1-18 was synthesized using (pyridin-4-yl)phenyl)pyrimidine (yield 50%).

m/z: 611.24 (100.0%), 612.24 (49.0%), 613.24 (12.1%), 614.25 (1.8%), 612.23 (1.1%)
m/z: 611.24 (100.0%), 612.24 (49.0%), 613.24 (12.1%), 614.25 (1.8%), 612.23 (1.1%)

화합물1Compound 1 -19-19

상기 화합물1-1과 같은 방법으로 중간체 I3 대신 중간체 I1로 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 4-chloro-2-phenyl-6-(3-(pyridin-3-yl)phenyl)pyrimidine를 이용하여 화합물 1-19를 합성하였다.(수율 50%)In the same manner as Compound 1-1, use Intermediate I1 instead of Intermediate I3 and 4-chloro-2-phenyl-6-(3- instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine. Compound 1-19 was synthesized using (pyridin-3-yl)phenyl)pyrimidine (yield 50%).

m/z: 611.24 (100.0%), 612.24 (49.0%), 613.24 (12.1%), 614.25 (1.8%), 612.23 (1.1%)
m/z: 611.24 (100.0%), 612.24 (49.0%), 613.24 (12.1%), 614.25 (1.8%), 612.23 (1.1%)

화합물 1-20Compound 1-20

상기 화합물1-1과 같은 방법으로 중간체 I3 대신 중간체 I1로 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 4-chloro-2-phenyl-6-(3-(pyridin-4-yl)phenyl)pyrimidine를 이용하여 화합물 1-20을 합성하였다.(수율 54%)In the same manner as Compound 1-1, use Intermediate I1 instead of Intermediate I3 and 4-chloro-2-phenyl-6-(3- instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine. Compound 1-20 was synthesized using (pyridin-4-yl)phenyl)pyrimidine (yield 54%).

m/z: 611.24 (100.0%), 612.24 (49.0%), 613.24 (12.1%), 614.25 (1.8%), 612.23 (1.1%)
m/z: 611.24 (100.0%), 612.24 (49.0%), 613.24 (12.1%), 614.25 (1.8%), 612.23 (1.1%)

[[ 화학식2Formula 2 ]의 합성] synthesis

화합물 2-1Compound 2-1

둥근바닥플라스크에 3-phenyl-9H-carbazole 5.0g, 3,3'-dibromo-1,1'-biphenyl 3.21g, t-BuONa 2.96g, Pd2(dba)3 0.75g, (t-Bu)3P 0.5ml를 톨루엔 100ml에 녹인 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결하였다. 유기층을 MC로 추출하고 감압여과한 후 컬럼정제 및 재결정하여 화합물2-1 8.64g (수율 66%)를 얻었다.In a round bottom flask, 5.0g of 3-phenyl-9H-carbazole, 3.21g of 3,3'-dibromo-1,1'-biphenyl, 2.96g of t-BuONa, 0.75g of Pd 2 (dba) 3 , (t-Bu) 0.5ml of 3P was dissolved in 100ml of toluene and stirred under reflux. The reaction was confirmed by TLC and the reaction was terminated after adding water. The organic layer was extracted with MC, filtered under reduced pressure, then column purified and recrystallized to obtain 8.64 g of Compound 2-1 (yield 66%).

m/z: 636.26 (100.0%), 637.26 (52.3%), 638.26 (13.6%), 639.27 (2.2%)
m/z: 636.26 (100.0%), 637.26 (52.3%), 638.26 (13.6%), 639.27 (2.2%)

화합물2Compound 2 -2-2

둥근바닥플라스크에 9-([1,1':3',1''-terphenyl]-5'-yl)-3-bromo-9H-carbazole 8.0g, (4-(9H-carbazol-9-yl)phenyl)boronic acid 4.85g을 톨루엔 200ml에 녹이고 K2CO3(2M) 25ml와 Pd(PPh3)4 0.6g을 넣은 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결시켰다. 유기층을 MC로 추출하고 감압여과한 후 재결정하여 화합물 2-2 7.62g (수율 71%)를 얻었다.8.0g of 9-([1,1':3',1''-terphenyl]-5'-yl)-3-bromo-9H-carbazole, (4-(9H-carbazol-9-yl) in a round bottom flask )phenyl)boronic acid 4.85g was dissolved in 200ml of toluene, 25ml of K 2 CO 3 (2M) and 0.6g of Pd(PPh 3 ) 4 were added, and then refluxed and stirred. The reaction was confirmed by TLC and the reaction was terminated after adding water. The organic layer was extracted with MC, filtered under reduced pressure, and recrystallized to obtain 7.62 g of compound 2-2 (yield 71%).

m/z: 636.26 (100.0%), 637.26 (52.3%), 638.26 (13.6%), 639.27 (2.2%)
m/z: 636.26 (100.0%), 637.26 (52.3%), 638.26 (13.6%), 639.27 (2.2%)

화합물2Compound 2 -3-3

둥근바닥플라스크에 9H,9'H-3,3'-bicarbazole 10.0g, 3-bromo-1,1'-biphenyl 14.1g, t-BuONa 4.4g, Pd2(dba)3 1.1g, (t-Bu)3P 2.5ml를 톨루엔 200ml에 녹인 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결하였다. 유기층을 MC로 추출하고 감압여과한 후 컬럼정제 및 재결정하여 화합물2-3 14.2g (수율 73%)를 얻었다.In a round bottom flask, 10.0g of 9H,9'H-3,3'-bicarbazole, 14.1g of 3-bromo-1,1'-biphenyl, 4.4g of t-BuONa, 1.1g of Pd 2 (dba) 3 , (t- Bu) 2.5ml of 3P was dissolved in 200ml of toluene and stirred under reflux. The reaction was confirmed by TLC and the reaction was terminated after adding water. The organic layer was extracted with MC, filtered under reduced pressure, then column purified and recrystallized to obtain 14.2 g of Compound 2-3 (yield 73%).

m/z: 636.26 (100.0%), 637.26 (52.3%), 638.26 (13.6%), 639.27 (2.2%)
m/z: 636.26 (100.0%), 637.26 (52.3%), 638.26 (13.6%), 639.27 (2.2%)

화합물2Compound 2 -4-4

둥근바닥플라스크에 9-phenyl-9H,9'H-3,3'-bicarbazole 5.0g, 3-bromo-1,1'-biphenyl 4.0g, t-BuONa 1.8g, Pd2(dba)3 0.5g, (t-Bu)3P 0.5ml를 톨루엔 70ml에 녹인 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결하였다. 유기층을 MC로 추출하고 감압여과한 후 컬럼정제 및 재결정하여 화합물2-4 5.33g (수율 67%)를 얻었다.In a round bottom flask, 5.0g of 9-phenyl-9H,9'H-3,3'-bicarbazole, 4.0g of 3-bromo-1,1'-biphenyl, 1.8g of t-BuONa, 0.5g of Pd 2 (dba) 3 , 0.5ml of (t-Bu) 3P was dissolved in 70ml of toluene and stirred under reflux. The reaction was confirmed by TLC and the reaction was terminated after adding water. The organic layer was extracted with MC, filtered under reduced pressure, then column purified and recrystallized to obtain 5.33 g of compound 2-4 (yield 67%).

m/z: 649.25 (100.0%), 650.26 (52.3%), 651.26 (13.4%), 652.26 (2.4%), 650.25 (1.1%)
m/z: 649.25 (100.0%), 650.26 (52.3%), 651.26 (13.4%), 652.26 (2.4%), 650.25 (1.1%)

화합물 2-5Compound 2-5

둥근바닥플라스크에 9-([1,1'-biphenyl]-3-yl)-3,6-dibromo-9H-carbazole 5.0g, 9H-carbazole 3.7g, t-BuONa 1.5g, Pd2(dba)3 0.4g, (t-Bu)3P 0.9ml를 톨루엔 70ml에 녹인 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결하였다. 유기층을 MC로 추출하고 감압여과한 후 컬럼정제 및 재결정하여 화합물2-5 4.22g (수율 62%)를 얻었다.In a round bottom flask, 5.0g of 9-([1,1'-biphenyl]-3-yl)-3,6-dibromo-9H-carbazole, 3.7g of 9H-carbazole, 1.5g of t-BuONa, Pd 2 (dba) 0.4g of 3 and 0.9ml of (t-Bu) 3P were dissolved in 70ml of toluene and stirred under reflux. The reaction was confirmed by TLC and the reaction was terminated after adding water. The organic layer was extracted with MC, filtered under reduced pressure, then column purified and recrystallized to obtain 4.22 g of Compound 2-5 (yield 62%).

m/z: 649.25 (100.0%), 650.26 (52.3%), 651.26 (13.4%), 652.26 (2.4%), 650.25 (1.1%)
m/z: 649.25 (100.0%), 650.26 (52.3%), 651.26 (13.4%), 652.26 (2.4%), 650.25 (1.1%)

유기발광소자의 제조Manufacturing of organic light emitting devices

도 1에 기재된 구조에 따라 유기발광소자를 제조하였다. 유기발광소자는 아래로부터 양극(정공주입전극(11))/정공주입층(12)/정공수송층(13)/발광층(14)/전자전달층(15)/음극(전자주입전극(16)) 순으로 적층되어 있다.An organic light emitting device was manufactured according to the structure shown in Figure 1. The organic light emitting device is, from below, an anode (hole injection electrode 11)/hole injection layer 12/hole transport layer 13/light emitting layer 14/electron transport layer 15/cathode (electron injection electrode 16). They are stacked in order.

실시예 및 비교예의 정공주입층(12), 정공전달층(13), 발광층(14), 전자전달층(15)은 아래과 같은 물질을 사용하였다.The following materials were used for the hole injection layer 12, hole transport layer 13, light emitting layer 14, and electron transport layer 15 of the examples and comparative examples.

유기발광소자 제작에 앞서 엑시플렉스에 의해 형성된 에너지가 인광도판트로 에너지 전이를 효율적으로 하기 위한 호스트1 및 호스트2의 조합을 알아보기 위해 유리 기판에 호스트1/호스트2 (1:1)를 증착하여 엑시플렉스 파장을 측정하였으며, 그 결과를 하기 표1에 나타내었다.Prior to manufacturing an organic light emitting device, Host 1/Host 2 (1:1) was deposited on a glass substrate to determine the combination of Host 1 and Host 2 to efficiently transfer the energy generated by Exiplex to the phosphorescent dopant. The exciplex wavelength was measured, and the results are shown in Table 1 below.

호스트1Host 1 호스트2Host 2 호스트1Host 1 :호스트2:host2 화합물compound T1T1 (eV) (eV) 화합물compound T1T1 (eV) (eV) 엑시플렉스Exiflex (nm)(nm) 조합예1Combination example 1 1-11-1 2.552.55 2-12-1 2.872.87 460460 조합예2Combination example 2 1-11-1 2.552.55 2-22-2 2.812.81 467467 조합예3Combination example 3 1-11-1 2.552.55 2-32-3 2.762.76 483483 조합예4Combination example 4 1-11-1 2.552.55 2-42-4 2.762.76 491491 조합예5Combination example 5 1-11-1 2.552.55 2-52-5 2.842.84 468468 조합예6Combination example 6 1-21-2 2.602.60 2-32-3 2.762.76 481481 조합예7Combination example 7 1-31-3 2.602.60 2-32-3 2.762.76 480480 조합예8Combination example 8 1-41-4 2.622.62 2-32-3 2.762.76 483483 조합예9Combination example 9 1-51-5 2.612.61 2-32-3 2.762.76 479479 조합예10Combination example 10 1-61-6 2.622.62 2-32-3 2.762.76 478478 조합예11Combination example 11 1-71-7 2.572.57 2-32-3 2.762.76 478478 조합예12Combination example 12 1-81-8 2.572.57 2-32-3 2.762.76 477477 조합예13Combination example 13 1-91-9 2.612.61 2-32-3 2.762.76 480480 조합예14Combination example 14 1-101-10 2.612.61 2-32-3 2.762.76 480480 조합예15Combination example 15 1-111-11 2.612.61 2-32-3 2.762.76 482482 조합예16Combination example 16 1-121-12 2.612.61 2-32-3 2.762.76 485485 조합예17Combination example 17 1-131-13 2.592.59 2-32-3 2.762.76 480480 조합예18Combination example 18 1-141-14 2.592.59 2-32-3 2.762.76 477477 조합예19Combination example 19 1-151-15 2.592.59 2-32-3 2.762.76 480480 조합예20Combination example 20 1-161-16 2.592.59 2-32-3 2.762.76 480480 조합예21Combination example 21 1-171-17 2.582.58 2-32-3 2.762.76 482482 조합예22Combination example 22 1-181-18 2.572.57 2-32-3 2.762.76 484484 조합예23Combination example 23 1-191-19 2.562.56 2-32-3 2.762.76 483483 조합예24Combination example 24 1-201-20 2.592.59 2-32-3 2.762.76 483483 조합비교예1Combination Comparison Example 1 CBPCBP 2.642.64 2-32-3 2.762.76 XX 조합비교예2Combination Comparison Example 2 Ref.1Ref.1 2.442.44 2-32-3 2.762.76 XX 조합비교예3Combination Comparison Example 3 Ref.2Ref.2 2.542.54 2-32-3 2.762.76 XX 조합비교예4Combination comparison example 4 Ref.3Ref.3 2.432.43 2-32-3 2.762.76 512512

상기 표1에서 보는 바와 같이 조합비교예1 내지 조합비교예3은 엑시플렉스에 의한 파장이 관측되지 않았으며, 조합비교예4의 경우 510nm 이상에서 파장이 관측되었다. 이는 녹색영역의 인광도판트의 흡수파장(최우측 460nm-490nm영역)을 고려할 때 에너지 전이가 비효율적으로 일어난다는 것을 알 수 있다.
As shown in Table 1, in Combination Comparative Examples 1 to 3, the wavelength due to exciplex was not observed, and in Combination Comparative Example 4, the wavelength was observed at 510 nm or more. This shows that energy transfer occurs inefficiently considering the absorption wavelength of the phosphorescent dopant in the green region (rightmost 460nm-490nm region).

유기발광소자의 제조Manufacturing of organic light emitting devices

실시예Example 1 One

인듐틴옥사이드(ITO)가 1500Å 두께가 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 이송 시킨 다음 산소 플라즈마를 이용하여 상기 기판을 5분간 세정 한 후 ITO 기판 상부에 열 진공 증착기(thermal evaporator)를 이용하여 정공주입층 HI01 600Å, 정공수송층으로 NPB 250Å을 제막하였다. 다음으로 상기 발광층으로 화합물1-1/Ir(ppy)3 10%로 도핑하여 300Å 제막하였다. 다음으로 전자전달층으로 ET01:Liq(1:1) 300Å 제막한 후 LiF 10Å, 알루미늄(Al) 1000Å 제막하고, 이 소자를 글로브 박스에서 밀봉(Encapsulation)함으로써 녹색 유기발광소자를 제작하였다.
A glass substrate coated with a 1500 Å thin film of indium tin oxide (ITO) was washed with distilled water ultrasonic waves. After washing with distilled water, the substrate is ultrasonic cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. The substrate is cleaned for 5 minutes using oxygen plasma, and then a thermal vacuum evaporator (thermal vacuum evaporator) is placed on the top of the ITO substrate. Using an evaporator, HI01 600Å was formed as a hole injection layer and NPB 250Å was formed as a hole transport layer. Next, the light emitting layer was doped with 10% of Compound 1-1/Ir(ppy) 3 to form a 300Å film. Next, a 300Å film of ET01:Liq (1:1) was deposited as an electron transport layer, followed by a 10Å layer of LiF and a 1000Å film of aluminum (Al), and the green organic light emitting device was manufactured by encapsulating the device in a glove box.

실시예Example 2 2

상기 실시예1의 발광층 호스트로 화합물1-1 대신 화합물1-5를 사용한 것을 제외하고는 동일한 방법으로 녹색 유기발광소자를 제작하였다.
A green organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 1-5 was used instead of Compound 1-1 as the emitting layer host.

실시예Example 3 3

상기 실시예1의 발광층 호스트로 화합물1-1 대신 화합물1-12를 사용한 것을 제외하고는 동일한 방법으로 녹색 유기발광소자를 제작하였다.
A green organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 1-12 was used instead of Compound 1-1 as the emitting layer host.

실시예Example 4 4

상기 실시예1의 발광층 호스트로 화합물1-1 대신 화합물1-14를 사용한 것을 제외하고는 동일한 방법으로 녹색 유기발광소자를 제작하였다.
A green organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 1-14 was used instead of Compound 1-1 as the emitting layer host.

실시예Example 5 5

상기 실시예1의 발광층 호스트로 화합물1-1 대신 화합물1-16을 사용한 것을 제외하고는 동일한 방법으로 녹색 유기발광소자를 제작하였다.
A green organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 1-16 was used instead of Compound 1-1 as the emitting layer host.

실시예Example 6 6

인듐틴옥사이드(ITO)가 1500Å 두께가 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 이송 시킨 다음 산소 플라즈마를 이용하여 상기 기판을 5분간 세정 한 후 ITO 기판 상부에 열 진공 증착기(thermal evaporator)를 이용하여 정공주입층 HI01 600Å, 정공수송층으로 NPB 250Å를 제막하였다. 다음으로 상기 발광층으로 화합물1-1:화합물2-1(6:4w%)혼합물/Ir(ppy)3 10%로 도핑하여 300 Å 제막하였다. 다음으로 전자전달층으로 ET01:Liq(1:1) 300Å 제막한 후 LiF 10Å, 알루미늄(Al) 1000Å 제막하고, 이 소자를 글로브 박스에서 밀봉(Encapsulation)함으로써 녹색 유기발광소자를 제작하였다.
A glass substrate coated with a 1500 Å thin film of indium tin oxide (ITO) was washed with distilled water ultrasonic waves. After cleaning with distilled water, ultrasonic cleaning with solvents such as isopropyl alcohol, acetone, and methanol, drying, and transferring to a plasma cleaner, the substrate is cleaned for 5 minutes using oxygen plasma, and then a thermal vacuum evaporator (thermal vacuum evaporator) is placed on the top of the ITO substrate. Using an evaporator, HI01 600Å was formed as a hole injection layer and NPB 250Å was formed as a hole transport layer. Next, the light emitting layer was doped with 10% of Compound 1-1: Compound 2-1 (6:4w%) mixture/Ir(ppy) 3 to form a 300 Å film. Next, a 300Å film of ET01:Liq (1:1) was deposited as an electron transport layer, followed by a 10Å layer of LiF and a 1000Å film of aluminum (Al), and the green organic light emitting device was manufactured by encapsulating the device in a glove box.

실시예Example 6 내지 6 to 실시예Example 25 25

실시예 1과 같은 방법으로 발광층 호스트로 화합물 1-2 내지 1-20:화합물2-2(6:4w%) 혼합물을 사용하여 제막한 녹색 유기발광소자를 제작하였다.
A green organic light-emitting device was manufactured using a mixture of Compounds 1-2 to 1-20:Compound 2-2 (6:4w%) as an emitting layer host in the same manner as in Example 1.

비교예1Comparative Example 1

상기 실시예1의 발광층 호스트로 CBP를 사용한 것을 제외하고는 동일한 방법으로 녹색 유기발광소자를 제작하였다.
A green organic light-emitting device was manufactured in the same manner as in Example 1, except that CBP was used as the light-emitting layer host.

비교예Comparative example 2 2

상기 실시예1의 발광층 호스트로 비교화합물(Ref.)1를 사용한 것을 제외하고는 동일한 방법으로 녹색 유기발광소자를 제작하였다.
A green organic light-emitting device was manufactured in the same manner as in Example 1, except that Comparative Compound (Ref.) 1 was used as the light-emitting layer host.

비교예3Comparative Example 3

상기 실시예1의 발광층 호스트로 비교화합물(Ref.)2를 사용한 것을 제외하고는 동일한 방법으로 녹색 유기발광소자를 제작하였다.
A green organic light-emitting device was manufactured in the same manner as in Example 1, except that Comparative Compound (Ref.) 2 was used as the light-emitting layer host.

비교예4Comparative Example 4

상기 실시예1의 발광층 호스트로 비교화합물(Ref.)3을 사용한 것을 제외하고는 동일한 방법으로 녹색 유기발광소자를 제작하였다.
A green organic light-emitting device was manufactured in the same manner as in Example 1, except that Comparative Compound (Ref.) 3 was used as the light-emitting layer host.

유기발광소자의 성능평가Performance evaluation of organic light emitting devices

키슬리 2400 소스 메져먼트 유닛(Kiethley 2400 source measurement unit) 으로 전압을 인가하여 전자 및 정공을 주입하고 코니카 미놀타(Konica Minolta) 분광복사계(CS-2000)를 이용하여 빛이 방출될 때의 휘도를 측정함으로써, 실시예 및 비교예의 유기발광소자의 성능을 인가전압에 대한 전류 밀도 및 휘도를 대기압 조건하에 측정하여 평가하였으며, 그 결과를 표 2에 나타내었다. Apply voltage to the Keithley 2400 source measurement unit to inject electrons and holes, and measure the luminance when light is emitted using a Konica Minolta spectroradiometer (CS-2000). By doing so, the performance of the organic light emitting devices of Examples and Comparative Examples was evaluated by measuring the current density and luminance with respect to the applied voltage under atmospheric pressure conditions, and the results are shown in Table 2.

Op. VOp. V QE(%)QE(%) Cd/ACd/A lm/wlm/w CIExCIEx CIEyCIey 수명@
10000nitlife span@
10000nit 실시예1Example 1 4.604.60 17.5117.51 42.6842.68 35.3135.31 0.3010.301 0.6210.621 5252 실시예2Example 2 4.574.57 17.6217.62 40.2140.21 35.0335.03 0.2990.299 0.6190.619 5555 실시예3Example 3 4.584.58 17.4917.49 41.8841.88 35.2235.22 0.2980.298 0.6200.620 4949 실시예4Example 4 4.554.55 17.7317.73 41.8141.81 35.5135.51 0.3000.300 0.6230.623 5353 실시예5Example 5 4.544.54 17.1917.19 43.2143.21 35.9935.99 0.2980.298 0.6140.614 5454 실시예6Example 6 4.104.10 17.8017.80 50.9250.92 40.2440.24 0.2980.298 0.6090.609 7070 실시예7Example 7 4.054.05 17.0117.01 51.0151.01 41.1241.12 0.2970.297 0.6180.618 7070 실시예8Example 8 4.004.00 17.2517.25 50.6550.65 40.0140.01 0.3020.302 0.6090.609 7575 실시예9Example 9 4.124.12 16.9016.90 51.2851.28 41.1241.12 0.3000.300 0.6200.620 6969 실시예10Example 10 4.104.10 17.4217.42 50.2550.25 43.9143.91 0.2990.299 0.6220.622 6868 실시예11Example 11 4.104.10 17.1617.16 50.1150.11 40.0040.00 0.2990.299 0.6240.624 6565 실시예12Example 12 4.094.09 16.9916.99 50.5250.52 42.9142.91 0.3010.301 0.6270.627 6464 실시예13Example 13 4.074.07 17.5517.55 50.0150.01 40.2240.22 0.2970.297 0.6240.624 6868 실시예14Example 14 4.084.08 17.2117.21 50.6550.65 40.0140.01 0.3020.302 0.6220.622 6464 실시예15Example 15 4.144.14 17.2317.23 51.2851.28 41.0041.00 0.3000.300 0.6250.625 7171 실시예16Example 16 4.104.10 17.0017.00 51.2551.25 42.7842.78 0.2990.299 0.6220.622 6969 실시예17Example 17 4.114.11 16.9716.97 50.1150.11 43.1443.14 0.2990.299 0.6230.623 6565 실시예18Example 18 4.104.10 16.9916.99 50.0050.00 40.1140.11 0.3020.302 0.6110.611 6666 실시예19Example 19 4.144.14 16.9716.97 51.0151.01 40.0140.01 0.3050.305 0.6150.615 7171 실시예20Example 20 4.154.15 17.0017.00 51.0051.00 41.5241.52 0.3050.305 0.6200.620 7272 실시예21Example 21 4.124.12 17.0017.00 50.4750.47 42.0042.00 0.3100.310 0.6130.613 7070 실시예22Example 22 4.104.10 17.3017.30 49.9049.90 40.5140.51 0.3000.300 0.6200.620 6666 실시예23Example 23 4.104.10 17.0717.07 50.1250.12 40.9040.90 0.2990.299 0.6240.624 6969 실시예24Example 24 4.104.10 17.1017.10 50.5450.54 40.1440.14 3.1103.110 0.6200.620 7070 실시예25Example 25 4.134.13 16.9016.90 52.1252.12 42.0242.02 3.1003.100 0.6170.617 7070 비교예1Comparative Example 1 5.025.02 6.436.43 13.1213.12 7.727.72 0.3010.301 0.6230.623 -- 비교예2Comparative example 2 5.315.31 11.5111.51 31.0131.01 27.8327.83 0.3010.301 0.6210.621 3535 비교예3Comparative Example 3 5.305.30 11.1011.10 31.0131.01 27.9527.95 0.3020.302 0.6250.625 3333 비교예4Comparative Example 4 4.964.96 12.7012.70 36.4036.40 31.4031.40 0.3100.310 0.6110.611 4343

상기 표1에 나타나는 바와 같이 본 발명의 실시예들은 비교예 1~3에 비하여 구동전압이 낮고 고효율 및 장수명을 가지는 것을 확인할 수 있으며, 모든 면에서 물성이 우수한 것을 알 수 있다. 비교예2 및 비교예3에 비하여 전자주입 및 수송이 용이한 호스트1 화합물을 사용함으로써 구동전압이 낮고 효율 및 수명이 상승하는 것을 알 수 있다. 또한 비교예4에 비하여 중간연결기로 헤테로아로마틱기를 추가로 가지는 경우 넓은 영역에서 전자주입 및 전자수송이 가능하므로 더욱이 구동전압이 낮아지고 효율이 상승하는 결과를 알 수 있다. 여기에 정공주입 및 수송이 용이한 호스트2 화합물을 같이 사용함으로써 더욱 구동전압이 낮아지고 고전류 밀도에서도 내구성이 좋아 장수명을 가지는 것을 확인할 수 있다. 이는 전자주입 및 수송이 용이한 호스트1 화합물에 정공주입 및 수송이 용이한 호스트2 화합물을 사용함으로써 구동전압을 낮추고, 발광층내 엑시톤을 효과적으로 가둬 효율을 증가시키고, 고전류 밀도에서 롤오프현상을 억제하며, 내구성이 좋아 장수명을 가지는 것을 알 수 있다.
As shown in Table 1, it can be seen that the Examples of the present invention have lower driving voltage, higher efficiency, and longer lifespan than Comparative Examples 1 to 3, and have excellent physical properties in all respects. It can be seen that the driving voltage is lower and the efficiency and lifespan are increased by using the host 1 compound, which is easy to inject and transport electrons compared to Comparative Examples 2 and 3. In addition, compared to Comparative Example 4, when a heteroaromatic group is additionally used as an intermediate linker, electron injection and electron transport are possible in a wide area, resulting in lower driving voltage and increased efficiency. By using the host 2 compound, which is easy to inject and transport holes, the driving voltage is further lowered and it is confirmed that it has good durability even at high current densities and has a long lifespan. This lowers the driving voltage by using the host 1 compound, which is easy to inject and transport electrons, and the host 2 compound, which is easy to inject and transport holes, increases efficiency by effectively trapping excitons in the light-emitting layer, and suppresses the roll-off phenomenon at high current densities. It can be seen that it is durable and has a long lifespan.

Claims (11)

하기 화학식 1-4로 표시되는 화합물:
[화학식 1-4]

상기 식에서,
X, Y, Z는 각각 독립적으로 N 또는 CR이며, X, Y, Z 중 적어도 2개는 N이고, X, Y 중 적어도 하나는 N이며, 여기서 R은 수소; 중수소; 중수소, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C6-50의 아릴기; 또는 중수소, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C2-50의 헤테로아릴기이고,
A는 각각 독립적으로 N 또는 CR0이며, 여기서 R0는 각각 독립적으로 수소; 중수소; 중수소로 치환되거나 치환되지 않은 C1-30의 알킬기; 중수소로 치환되거나 치환되지 않은 C2-30의 알케닐기; 또는 중수소로 치환되거나 치환되지 않은 C2-30의 알키닐기이다.
Compounds represented by the following formula 1-4:
[Formula 1-4]

In the above equation,
X, Y, and Z are each independently N or CR, at least two of X, Y, and Z are N, and at least one of X and Y is N, where R is hydrogen; heavy hydrogen; C 6- substituted or unsubstituted with deuterium, a C 1-30 alkyl group, a C 2-30 alkenyl group, a C 2-30 alkynyl group, a C 6-30 aryl group, or a C 2-30 heteroaryl group 50 aryl group; or C 2 substituted or unsubstituted with deuterium, a C 1-30 alkyl group, a C 2-30 alkenyl group, a C 2-30 alkynyl group, a C 6-30 aryl group, or a C 2-30 heteroaryl group It is a heteroaryl group of -50 ,
A is each independently N or CR 0 , where R 0 is each independently hydrogen; heavy hydrogen; C 1-30 alkyl group substituted or unsubstituted with deuterium; C 2-30 alkenyl group substituted or unsubstituted with deuterium; Or it is a C 2-30 alkynyl group substituted or unsubstituted with deuterium.
 삭제delete 제1항에 있어서,
하기 화학식들 중 어느 하나로 표시되는 화합물:
, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,
, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,

, , , , , , ,According to paragraph 1,
Compounds represented by any of the following formulas:
, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,
, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,

, , , , , , , 애노드(anode), 캐소드(cathode) 및 두 전극 사이에 제1항 기재의 화합물을 함유하는 1층 이상의 유기물층을 포함하는 유기발광소자.An organic light-emitting device comprising an anode, a cathode, and one or more organic layers containing the compound according to claim 1 between the two electrodes. 제4항에 있어서,
상기 유기물층이 발광층, 전자주입층 또는 전자수송층인 유기발광소자.According to paragraph 4,
An organic light-emitting device wherein the organic material layer is a light-emitting layer, an electron injection layer, or an electron transport layer. 제5항에 있어서,
상기 발광층이 화학식 1-4로 표시되는 화합물을 발광호스트로 포함하는 유기발광소자.According to clause 5,
An organic light-emitting device wherein the light-emitting layer includes a compound represented by Formula 1-4 as a light-emitting host. 제6항에 있어서,
상기 발광층이 화학식 1-4로 표시되는 화합물 및 하기 화학식 2로 표시되는 화합물을 포함하는 유기발광소자:
[화학식 2]

상기 화학식 2에서 r1 내지 r8은 각각 독립적으로 수소; 중수소; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1-30의 알킬기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알케닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알키닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1-30의 알콕시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6-30의 아릴옥시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C6-50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C2-50의 헤테로아릴기이며,
Ar은 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은C6-50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C2-50의 헤테로아릴기이고,
m은 1 내지 4의 정수이며,
m이 2내지 4일 때, Ar 및 r1~r8은 서로 연결될 수 있다.According to clause 6,
An organic light-emitting device in which the light-emitting layer includes a compound represented by Formula 1-4 and a compound represented by Formula 2 below:
[Formula 2]

In Formula 2, r 1 to r 8 are each independently hydrogen; heavy hydrogen; C 1-30 alkyl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, or nitro group; C 2-30 alkenyl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, or nitro group; C 2-30 alkynyl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, or nitro group; C 1-30 alkoxy group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, or nitro group; C 6-30 aryloxy group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, or nitro group; Deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryloxy group Period, a C 6-30 aryl group, or a C 6-50 aryl group substituted or unsubstituted with a C 2-30 heteroaryl group; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryl It is a C 2-50 heteroaryl group substituted or unsubstituted with an oxy group, a C 6-30 aryl group, or a C 2-30 heteroaryl group,
Ar is deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 An aryloxy group, a C 6-30 aryl group, or a C 6-50 aryl group substituted or unsubstituted with a C 2-30 heteroaryl group; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryl It is a C 2-50 heteroaryl group substituted or unsubstituted with an oxy group, a C 6-30 aryl group, or a C 2-30 heteroaryl group,
m is an integer from 1 to 4,
When m is 2 to 4, Ar and r 1 to r 8 may be connected to each other. 제7항에 있어서,
상기 화학식 2로 표시되는 화합물이 하기 화학식 2-1 내지 2-7로 표시되는 화합물 중 어느 하나인 유기발광소자:
[화학식 2-1]

[화학식 2-2]

[화학식 2-3]

[화학식 2-4]

[화학식 2-5]

[화학식 2-6]

[화학식 2-7]

상기 식들에서 Ar1, Ar2, Ar3, Ar4 , Ar5는 각각 독립적으로 상기 화학식 2의 Ar의 정의와 같으며,
R1, R2, R3, R4는 상기 화학식 2의 r1 내지 r8의 정의와 같으며,
a, b 각각 독립적으로 0 내지 3의 정수이다.In clause 7,
An organic light-emitting device in which the compound represented by Formula 2 is any one of the compounds represented by Formulas 2-1 to 2-7:
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

[Formula 2-7]

In the above formulas, Ar 1 , Ar 2 , Ar 3 , Ar 4 , and Ar 5 are each independently the same as the definition of Ar in Formula 2,
R 1 , R 2 , R 3 , and R 4 are as defined for r 1 to r 8 in Formula 2 above,
a and b are each independently an integer from 0 to 3. 제8항에 있어서,
상기 화학식 2로 표시되는 화합물이 하기 화학식으로 표시되는 화합물 중 어느 하나인 유기발광소자:
, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , According to clause 8,
An organic light-emitting device in which the compound represented by Formula 2 is any one of the compounds represented by the following formula:
, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , 제8항에 있어서,
상기 화학식 1-4 및 화학식 2를 통하여 형성된 엑시플렉스 발광파장이 400-650 nm인 유기발광소자.According to clause 8,
An organic light-emitting device having an exciplex emission wavelength of 400-650 nm formed through Formula 1-4 and Formula 2. 제8항에 있어서,
상기 화학식 1-4 및 화학식 2를 통하여 형성된 엑시플렉스 발광파장이 발광층의 게스트인 도판트의 발광파장보다 단파장에서 형성되는 유기발광소자.
According to clause 8,
An organic light-emitting device in which the exciplex emission wavelength formed through Formulas 1-4 and 2 is shorter than the emission wavelength of the dopant, which is a guest of the light-emitting layer.
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