KR20220138845A - Novel compound and organic electroluminescent device comprising same - Google Patents

Novel compound and organic electroluminescent device comprising same Download PDF

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KR20220138845A
KR20220138845A KR1020220124623A KR20220124623A KR20220138845A KR 20220138845 A KR20220138845 A KR 20220138845A KR 1020220124623 A KR1020220124623 A KR 1020220124623A KR 20220124623 A KR20220124623 A KR 20220124623A KR 20220138845 A KR20220138845 A KR 20220138845A
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deuterium
halogen
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KR102630946B1 (en
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함호완
김봉기
안현철
김성훈
김동준
배유진
조지은
이형진
임동환
안자은
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주식회사 동진쎄미켐
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Abstract

A novel compound of the present invention has a HOMO energy level for easy hole injection, a high LUMO energy level for blocking electrons, excellent hole transport properties, and thus when applied to a hole injection layer, a hole transport layer, or a hole transport auxiliary layer in an organic light emitting device, stability and long lifespan due to excellent low voltage, high efficiency, and high Tg can be obtained.

Description

신규한 화합물 및 이를 포함하는 유기발광소자{NOVEL COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING SAME}Novel compound and organic light emitting device comprising the same

본 발명은 신규한 화합물 및 이를 포함하는 유기발광소자에 관한 것으로, 특히 정공주입, 정공수송물질, 또는 정공수송보조물질로 유용한 화합물에 관한 것이다.The present invention relates to a novel compound and an organic light emitting device including the same, and more particularly, to a compound useful as a hole injection, hole transport material, or hole transport auxiliary material.

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, the organic light emitting device capable of low voltage driving as a self-luminous type has excellent viewing angle and contrast ratio, and does not require a backlight, compared to liquid crystal display (LCD), which is the mainstream of flat panel display devices. It is advantageous in terms of power consumption and has a wide color reproduction range, attracting attention as a next-generation display device.

유기발광소자에서 유기물 층으로 사용되는 재료는 크게 기능에 따라, 발광 재료, 정공주입 재료, 정공수송 재료, 정공수송보조재료, 전자수송 재료, 전자주입 재료 등으로 분류될 수 있다.Materials used as organic layers in organic light emitting devices may be classified into light emitting materials, hole injection materials, hole transport materials, hole transport auxiliary materials, electron transport materials, electron injection materials, and the like, according to their functions.

현재까지 이러한 유기발광소자에 사용되는 정공주입·정공수송 재료에는 카바졸 골격을 가지는 아민 유도체가 많이 연구되었으나 보다 높은 구동전압, 낮은 효율 및 짧은 수명으로 인해 실용화하는 데에 많은 어려움이 있었다. 따라서 우수한 특성을 갖는 물질을 이용하여 저전압 구동, 고휘도 및 장수명을 갖는 유기발광소자를 개발하려는 노력이 지속되어 왔다.Until now, many amine derivatives having a carbazole skeleton have been studied for hole injection and hole transport materials used in organic light emitting devices, but there were many difficulties in practical application due to higher driving voltage, low efficiency and short lifespan. Therefore, efforts have been made to develop an organic light emitting diode having low voltage driving, high luminance, and long lifespan by using a material having excellent properties.

상기와 같은 문제점을 해결하기 위해, 본 발명은 정공주입이 용이한 HOMO 에너지 레벨을 가지며, 전자를 차단할 수 있는 높은 LUMO 에너지 레벨을 가지며, 정공수송 특성이 우수하고, 유기발광소자의 정공주입층, 정공수송층 또는 정공수송보조층에 적용시 우수한 저전압, 고효율, 높은 Tg로 인한 안정성 및 장수명을 가지게 할 수 있는 신규한 화합물을 제공하는 것을 목적으로 한다.In order to solve the above problems, the present invention has a HOMO energy level for easy hole injection, a high LUMO energy level for blocking electrons, excellent hole transport characteristics, and a hole injection layer of an organic light emitting device, An object of the present invention is to provide a novel compound capable of having excellent low voltage, high efficiency, high Tg stability and long lifespan when applied to a hole transport layer or a hole transport auxiliary layer.

본 발명은 또한 상기 화합물을 포함하여 정공주입 및 정공수송 특성이 향상되고, 동시에 전자차단 특성을 가지며, 우수한 저전압, 고효율, 높은 Tg로 인한 안정성 및 장수명을 가지는 유기발광소자를 제공하는 것을 목적으로 한다.The present invention also aims to provide an organic light emitting device having improved hole injection and hole transport characteristics, including the compound, at the same time having electron blocking properties, excellent low voltage, high efficiency, stability due to high Tg, and long life. .

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

[화학식 1][Formula 1]

Figure pat00001
Figure pat00001

상기 화학식 1에서,In Formula 1,

Ar은 각각 독립적으로 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6-50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-50의 헤테로아릴기이고, Ar is each independently a C 6-50 aryl group substituted with or unsubstituted with deuterium, a halogen, an amino group, a nitrile group, or a nitro group; Or a C 2-50 heteroaryl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group,

R1 및 R2는 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 C6-50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-50의 헤테로아릴기이며, R1 및 R2는 서로 고리를 형성할 수 있으며,R 1 and R 2 are each independently hydrogen; heavy hydrogen; a C 1-30 alkyl group substituted with or unsubstituted with deuterium, a halogen, an amino group, a nitrile group, or a nitro group; C 2-30 alkenyl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C 2-30 alkynyl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; a C 1-30 alkoxy group substituted or unsubstituted with deuterium, a halogen, an amino group, a nitrile group, or a nitro group; C 6-30 aryloxy group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C 6-50 aryl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; Or deuterium, halogen, amino group, nitrile group, nitro group substituted or unsubstituted C 2-50 heteroaryl group, R 1 and R 2 may form a ring with each other,

o는 0 내지 3의 정수이고,o is an integer from 0 to 3,

p, q는 각각 독립적으로 1 내지 4의 정수이다.p and q are each independently an integer of 1 to 4.

또한, 본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기발광소자를 제공한다.In addition, the present invention provides an organic light emitting device comprising the compound represented by the formula (1).

본 발명의 화합물은 정공주입이 용이한 HOMO 에너지 레벨을 가지며, 전자를 차단할 수 있는 높은 LUMO 에너지 레벨을 가지며, 정공수송 특성이 우수하고, 유기발광소자의 정공주입층, 정공수송층 또는 정공수송보조층에 적용시 우수한 저전압, 고효율, 높은 Tg로 인한 안정성 및 장수명을 가지게 할 수 있다.The compound of the present invention has a HOMO energy level that facilitates hole injection, has a high LUMO energy level that can block electrons, has excellent hole transport characteristics, and is a hole injection layer, a hole transport layer or a hole transport auxiliary layer of an organic light emitting device. It can have excellent low voltage, high efficiency, high Tg stability and long lifespan when applied to

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: 음극1 schematically shows a cross-section of an OLED according to an embodiment of the present invention.
drawing sign
10: substrate
11: positive electrode
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 in that it is represented by the following formula (1).

[화학식 1][Formula 1]

Figure pat00002
Figure pat00002

상기 화학식 1에서,In Formula 1,

Ar은 각각 독립적으로 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6-50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-50의 헤테로아릴기이고, Ar is each independently a C 6-50 aryl group substituted with or unsubstituted with deuterium, a halogen, an amino group, a nitrile group, or a nitro group; Or a C 2-50 heteroaryl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group,

R1 및 R2는 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 C6-50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-50의 헤테로아릴기이며, R1 및 R2는 서로 고리를 형성할 수 있으며,R 1 and R 2 are each independently hydrogen; heavy hydrogen; a C 1-30 alkyl group substituted with or unsubstituted with deuterium, a halogen, an amino group, a nitrile group, or a nitro group; C 2-30 alkenyl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C 2-30 alkynyl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; a C 1-30 alkoxy group substituted or unsubstituted with deuterium, a halogen, an amino group, a nitrile group, or a nitro group; C 6-30 aryloxy group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C 6-50 aryl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; Or deuterium, halogen, amino group, nitrile group, nitro group substituted or unsubstituted C 2-50 heteroaryl group, R 1 and R 2 may form a ring with each other,

o는 0 내지 3의 정수이고,o is an integer from 0 to 3,

p, q는 각각 독립적으로 1 내지 4의 정수이다.p and q are each independently an integer of 1 to 4.

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

Figure pat00003
Figure pat00004
Figure pat00005
Figure pat00006
Figure pat00007
Figure pat00008
Figure pat00009
Figure pat00010
Figure pat00011
Figure pat00012
Figure pat00013
Figure pat00014
Figure pat00015
Figure pat00016
Figure pat00017
Figure pat00018
Figure pat00019
Figure pat00020
Figure pat00021
Figure pat00022
Figure pat00023
Figure pat00024
Figure pat00003
Figure pat00004
Figure pat00005
Figure pat00006
Figure pat00007
Figure pat00008
Figure pat00009
Figure pat00010
Figure pat00011
Figure pat00012
Figure pat00013
Figure pat00014
Figure pat00015
Figure pat00016
Figure pat00017
Figure pat00018
Figure pat00019
Figure pat00020
Figure pat00021
Figure pat00022
Figure pat00023
Figure pat00024

Figure pat00025
Figure pat00026
Figure pat00027
Figure pat00028
Figure pat00029
Figure pat00030
Figure pat00031
Figure pat00032
Figure pat00033
Figure pat00034
Figure pat00035
Figure pat00036
Figure pat00037
Figure pat00038
Figure pat00039
Figure pat00040
Figure pat00041
Figure pat00042
Figure pat00043
Figure pat00044
Figure pat00045
Figure pat00025
Figure pat00026
Figure pat00027
Figure pat00028
Figure pat00029
Figure pat00030
Figure pat00031
Figure pat00032
Figure pat00033
Figure pat00034
Figure pat00035
Figure pat00036
Figure pat00037
Figure pat00038
Figure pat00039
Figure pat00040
Figure pat00041
Figure pat00042
Figure pat00043
Figure pat00044
Figure pat00045

Figure pat00046
Figure pat00047
Figure pat00048
Figure pat00049
Figure pat00050
Figure pat00051
Figure pat00052
Figure pat00053
Figure pat00054
Figure pat00055
Figure pat00056
Figure pat00057
Figure pat00058
Figure pat00059
Figure pat00060
Figure pat00061
Figure pat00062
Figure pat00063
Figure pat00064
Figure pat00065
Figure pat00066
Figure pat00067
Figure pat00068
Figure pat00069
Figure pat00070
Figure pat00071
Figure pat00072
Figure pat00073
Figure pat00074
Figure pat00075
Figure pat00076
Figure pat00077
Figure pat00078
Figure pat00079
Figure pat00080
Figure pat00081
Figure pat00082
Figure pat00083
Figure pat00084
Figure pat00085
Figure pat00046
Figure pat00047
Figure pat00048
Figure pat00049
Figure pat00050
Figure pat00051
Figure pat00052
Figure pat00053
Figure pat00054
Figure pat00055
Figure pat00056
Figure pat00057
Figure pat00058
Figure pat00059
Figure pat00060
Figure pat00061
Figure pat00062
Figure pat00063
Figure pat00064
Figure pat00065
Figure pat00066
Figure pat00067
Figure pat00068
Figure pat00069
Figure pat00070
Figure pat00071
Figure pat00072
Figure pat00073
Figure pat00074
Figure pat00075
Figure pat00076
Figure pat00077
Figure pat00078
Figure pat00079
Figure pat00080
Figure pat00081
Figure pat00082
Figure pat00083
Figure pat00084
Figure pat00085

본 발명에 따른 화학식 1의 화합물은 정공주입이 용이한 HOMO 에너지 레벨을 가지며, 전자를 차단할 수 있는 높은 LUMO 에너지 레벨을 가지며, 정공수송 특성이 우수하고, 유기발광소자의 정공주입층, 정공수송층, 또는 정공수송보조층에 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 a HOMO energy level that facilitates hole injection, has a high LUMO energy level that can block electrons, has excellent hole transport characteristics, and has a hole injection layer, a hole transport layer, Alternatively, when applied to the hole transport auxiliary layer, it can have excellent low voltage, high efficiency, and stability and long life due to high Tg.

또한 본 발명의 화합물은 다음과 같은 과정을 거쳐 제조될 수 있다.In addition, the compound of the present invention can be prepared through the following process.

[반응식 1][Scheme 1]

Figure pat00086
Figure pat00086

상기 반응식에서, 목적화합물은 화학식 1로 표시되는 화합물이며, Ar, R1, R2, o, p, q는 화학식 1에서 정의한 바와 같다.In the above scheme, the target compound is a compound represented by Formula 1, and Ar, R 1 , R 2 , o, p, and q are as defined in Formula 1.

또한, 본 발명은 상기 화학식 1로 표시되는 화합물을 유기물층에 포함하는 유기발광소자를 제공한다. 이때, 본 발명의 화합물은 바람직하기로는 정공주입물질, 정공수송물질, 또는 정공수송보조물질로 단독으로 사용되거나 또는 공지의 정공주입, 정공수송물질, 또는 정공수송보조물질과 함께 사용될 수 있다.In addition, the present invention provides an organic light emitting device comprising the compound represented by Formula 1 in an organic material layer. In this case, the compound of the present invention is preferably used alone as a hole injection material, a hole transport material, or a hole transport auxiliary material, or it may be used together with a known hole injection, hole transport material, or hole transport auxiliary material.

또한 본 발명의 유기발광소자는 상기 화학식 1로 표시되는 화합물을 포함하는 1층 이상의 유기물층을 포함하는 바, 일예로 상기 유기발광소자의 제조방법을 설명하면 다음과 같다.In addition, the organic light emitting device of the present invention includes one or more organic material layers including the compound represented by Chemical Formula 1, and a method of manufacturing the organic light emitting device will be described as an example 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. 또한 상기 정공수송층과 발광층 사이에 정공수송보조층을 더욱 포함할 수 있다.The organic light emitting device includes an organic material layer such as a hole injection layer (HIL), a hole transport layer (HTL), a light emitting 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. In addition, a hole transport auxiliary layer may be further included between the hole transport layer and the light emitting layer.

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 having a high work function on a substrate. In this case, as the substrate, a substrate used in a conventional organic light emitting device may be used, and in particular, it is preferable to use a glass substrate or a transparent plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance. In addition, transparent and excellent indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc. may be used as the material for the anode electrode. The material for the anode electrode may be deposited by a conventional anode forming method, and specifically, may be deposited by a 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 있지만, 균일한 막질을 얻기 쉽고, 또한 핀정공이 발생하기 어렵다는 등의 점에서 진공증착법에 의해 형성하는 것이 바람직하다. 상기 진공증착법에 의해 정공주입층을 형성하는 경우 그 증착조건은 정공주입층의 재료로서 사용하는 화합물, 목적하는 정공주입층의 구조 및 열적특성 등에 따라 다르지만, 일반적으로 50-500 ℃의 증착온도, 10-8 내지 10-3 torr의 진공도, 001 내지 100 Å/sec의 증착 속도, 10 Å 내지 5 ㎛의 층 두께 범위에서 적절히 선택하는 것이 바람직하다.Then, the hole injection layer material on the anode electrode can be formed by a method such as vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett) method, etc., but it is easy to obtain a uniform film quality, and also It is preferable to form by the vacuum evaporation method from the point of being difficult to generate|occur|produce. In the case of forming the hole injection layer by the vacuum deposition method, the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal characteristics of the desired hole injection layer, etc., but in general, a deposition temperature of 50-500 ℃, It is preferable to appropriately select a vacuum degree of 10 -8 to 10 -3 torr, a deposition rate of 001 to 100 Å/sec, and a layer thickness of 10 Å to 5 μm.

상기 정공주입층 물질은 본 발명의 화학식 1로 표시되는 화합물이 단독으로 사용되거나 또는 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.As the hole injection layer material, the compound represented by Formula 1 of the present invention may be used alone or a known hole injection layer material may be used. For example, a phthalocyanine compound such as copper phthalocyanine disclosed in US Patent No. 4,356,429 or starburst Type amine derivatives 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) may be used as the hole injection layer material.

다음으로 상기 정공주입층 상부에 정공수송층 물질을 진공증착법, 스핀코팅법, 캐스트법, LB법 등과 같은 방법에 의해 형성할 수 있지만, 균일한 막질을 얻기 쉽고, 핀정공이 발생하기 어렵다는 점에서 진공증착법에 의해 형성하는 것이 바람직하다. 상기 진공증착법에 의해 정공수송층을 형성하는 경우 그 증착조건은 사용하는 화합물에 따라 다르지만 일반적으로 정공주입층의 형성과 거의 동일한 조건 범위에서 선택하는 것이 좋다.Next, the hole transport layer material on the hole injection layer can be formed by a method such as vacuum deposition, spin coating, casting, LB method, etc., but it is easy to obtain a uniform film quality, It is preferable to form by vapor deposition. In the case of forming the hole transport layer by the vacuum deposition method, the deposition conditions vary depending on the compound used, but in general, it is preferable to select within the same range of conditions as those for the formation of the hole injection layer.

또한, 상기 정공수송층 물질은 본 발명의 화학식 1로 표시되는 화합물이 단독으로 사용되거나 또는 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), NN'-디(나프탈렌-1-일)-N,N'-디페닐 벤지딘(α-NPD) 등의 방향족 축합환을 가지는 통상의 아민 유도체 등이 사용될 수 있다.In addition, as the hole transport layer material, the compound represented by Formula 1 of the present invention may be used alone or a mixture of known hole transport layer materials may be used. Specifically, the known hole transport layer material includes carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1, 1-biphenyl]-4,4'-diamine (TPD), NN'-di(naphthalen-1-yl)-N,N'-diphenyl benzidine (α-NPD) amine derivatives and the like can be used.

그 후, 상기 정공수송층 상부에 발광층 물질을 진공증착법, 스핀코팅법, 캐스트법, LB법 등과 같은 방법에 의해 형성할 수 있지만, 균일한 막질을 얻기 쉽고, 핀정공이 발생하기 어렵다는 점에서 진공증착법에 의해 형성하는 것이 바람직하다. 상기 진공증착법에 의해 발광층을 형성하는 경우 그 증착조건은 사용하는 화합물에 따라 다르지만 일반적으로 정공주입층의 형성과 거의 동일한 조건 범위에서 선택하는 것이 좋다. 또한, 상기 발광층 재료는 공지의 호스트 또는 도펀트로 사용할 수 있다. 일예로 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. 도펀트의 도핑농도는 특별히 제한되지 않으나, 호스트 100 중량부 대비 도펀트가 0.01 내지 15 중량부로 도핑되는 것이 바람직하다.Thereafter, the light emitting layer material on the hole transport layer can be formed by methods such as vacuum deposition, spin coating, casting, LB, etc., but it is easy to obtain a uniform film quality and it is difficult to generate pin holes. It is preferable to form by In the case of forming the light emitting layer by the vacuum deposition method, the deposition conditions vary depending on the compound used, but in general, it is preferable to select it within the same range of conditions as those for the formation of the hole injection layer. In addition, the light emitting layer material may be used as a known host or dopant. For example, as a fluorescent dopant, IDE102 or IDE105, or BD142 (N 6 ,N 12 -bis(3,4-dimethylphenyl)-N 6 ,N 12 -dimethylchrysene- 6,12-diamine) can be used, and the phosphorescent dopant is a green phosphorescent dopant Ir(ppy) 3 (tris(2-phenylpyridine) iridium), and a blue phosphorescent dopant F2Irpic (iridium(III) bis[4,6- Difluorophenyl)-pyridinato-N,C2'] picolinic acid salt), UDC's red phosphorescent dopant RD61, etc. may be co-evacuated (doped). The doping concentration of the dopant is not particularly limited, but it is preferable that the dopant be doped in an amount of 0.01 to 15 parts by weight relative to 100 parts by weight of the host.

또한, 발광층에 인광 도펀트와 함께 사용할 경우에는 삼중항 여기자 또는 정공이 전자수송층으로 확산되는 현상을 방지하기 위하여 정공억제재료(HBL)를 추가로 진공증착법 또는 스핀코팅법에 의해 적층시키는 것이 바람직하다. 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: UDC사BCP(바쏘쿠프로인)) 등을 사용할 수 있다.In addition, when used together with a phosphorescent dopant in the light emitting layer, in order to prevent a phenomenon in which triplet excitons or holes are diffused into the electron transport layer, it is preferable to further laminate a hole blocking material (HBL) by vacuum deposition or spin coating. At this time, the hole-blocking material that can be used is not particularly limited, and any one of known hole-blocking materials used as a hole-blocking material can be selected and used. For example, an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, or a hole-inhibiting material described in Japanese Patent Application Laid-Open No. Hei 11-329734 (A1), etc. are mentioned. Representatively, Balq (bis(8-hyde) Roxy-2-methylquinolinol nato)-aluminum biphenoxide), phenanthrolines-based compounds (eg, UDC's BCP (vasocuproin)), and the like may be used.

상기와 같이 형성된 발광층 상부에는 전자수송층이 형성되는데, 이때 상기 전자수송층은 진공증착법, 스핀코팅법, 캐스트법 등의 방법으로 형성되며, 특히 진공증착법에 의해 형성하는 것이 바람직하다.An electron transport layer is formed on the light emitting layer formed as described above. In this case, the electron transport layer is formed by a vacuum deposition method, a spin coating method, a casting method, etc., and is particularly preferably formed by a vacuum deposition method.

상기 전자수송층 재료는 전자주입전극으로부터 주입된 전자를 안정하게 수송하는 기능을 하는 것으로서 그 종류가 특별히 제한되지는 않으며, 예를 들어 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. 또한, 전자수송층 상부에 캐소드로부터 전자의 주입을 용이하게 하는 기능을 가지는 물질인 전자주입층(EIL)이 적층될 수 있으며, 전자주입층 물질로는 LiF, NaCl, CsF, Li2O, BaO 등의 물질을 이용할 수 있다.The electron transport layer material functions to stably transport electrons injected from the electron injection electrode, and the type thereof is not particularly limited. For example, a quinoline derivative, particularly tris(8-quinolinolato)aluminum (Alq 3 ) ), or ET4 (6,6'-(3,4-dimethyl-1,1-dimethyl-1H-silol-2,5-diyl)di-2,2'-bipyridine) can be used. In addition, an electron injection layer (EIL), which is a material having a function of facilitating the injection of electrons from the cathode, may be stacked on the electron transport layer, and as the electron injection layer material, LiF, NaCl, CsF, Li 2 O, BaO, etc. material can be used.

또한, 상기 전자수송층의 증착조건은 사용하는 화합물에 따라 다르지만, 일반적으로 정공주입층의 형성과 거의 동일한 조건 범위에서 선택하는 것이 좋다.In addition, although the deposition conditions of the electron transport layer vary depending on the compound used, in general, it is preferable to select the electron transport layer within the same range of conditions as those for the formation of the hole injection layer.

그 뒤, 상기 전자수송층 상부에 전자주입층 물질을 형성할 수 있으며, 이때 상기 전자수송층은 통상의 전자주입층 물질을 진공증착법, 스핀코팅법, 캐스트법 등의 방법으로 형성되며, 특히 진공증착법에 의해 형성하는 것이 바람직하다.Thereafter, an electron injection layer material may be formed on the electron transport layer, in which case the electron transport layer is formed by vacuum deposition, spin coating, casting, etc., of a conventional electron injection layer material, particularly in a vacuum deposition method. It is preferable to form by

마지막으로 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 on the electron injection layer is formed by a method such as a vacuum deposition method or a sputtering method and used as a cathode. Here, as the metal for forming the cathode, a metal having a low work function, an alloy, an electrically conductive compound, and a mixture thereof may be used. 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 this. In addition, in order to obtain a top light emitting device, a transmissive cathode using ITO or IZO may be used.

또한 본 발명의 유기발광소자는 상기 정공수송층과 발광층 사이에 정공수송보조층을 더욱 포함할 수 있다. 상기 정공수송보조층은 대한민국특허공개 제10-2010-0015029호에 기재된 것과 같은 공지의 방법을 통하여 형성될 수 있으며, 바람직하게는 본 발명의 화합물 1을 정공수송보조물질로 사용하여 정공수송보조층을 형성할 수 있다.In addition, the organic light emitting device of the present invention may further include a hole transport auxiliary layer between the hole transport layer and the light emitting layer. The hole transport auxiliary layer may be formed through a known method as described in Korean Patent Application Laid-Open No. 10-2010-0015029, and preferably, the hole transport auxiliary layer using Compound 1 of the present invention as a hole transport auxiliary material. can form.

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. 바람직하기로 본 발명의 유기발광소자는 정공수송보조층을 더욱 포함한다.The organic light emitting device of the present invention may have an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an organic light emitting device having a cathode structure, as well as a structure of an organic light emitting device of various structures is possible, if necessary, 1 It is also possible to further form a layer or an intermediate layer of two layers. Preferably, the organic light emitting device of the present invention further comprises a hole transport auxiliary layer.

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

본 발명의 유기발광소자는 정공주입 및 정공수송 특성이 향상되고, 동시에 전자차단 특성을 가지며, 우수한 저전압, 고효율, 높은 Tg로 인한 안정성 및 장수명 등의 우수한 소자 특성을 가진다.The organic light emitting device of the present invention has improved hole injection and hole transport properties, and at the same time has electron blocking properties, and has excellent device characteristics such as excellent low voltage, high efficiency, stability due to high Tg and long life.

이하 본 발명의 이해를 돕기 위하여 바람직한 실시예를 제시한다. 그러나 하기의 실시예는 본 발명을 더욱 쉽게 이해하기 위하여 제공되는 것일 뿐, 실시예에 의하여 본 발명의 내용이 한정되는 것은 아니다.Hereinafter, preferred examples are presented to help the understanding of the present invention. However, the following examples are only provided for easier understanding of the present invention, and the content of the present invention is not limited by the examples.

중간체 1-1의 합성Synthesis of Intermediate 1-1

Figure pat00087
Figure pat00087

질소 기류 하에서 (4-bromophenyl)hydrazine hydrochloride 25 g을 아세트산 700 ml으로 녹인 후, 여기에 3,3-dimethyl-2,3-dihydro-1H-inden-1-one 25 g을 넣은 후 실온에서 1시간 교반 후 12시간동안 환류 교반하였다. 실온으로 냉각시킨 후, 아세트산을 농축하여 생성된 고체를 필터링한 후 MC와 헥산으로 재결정하여 중간체 1-1 31.53 g (수율 52%)을 얻었다.Dissolve 25 g of (4-bromophenyl)hydrazine hydrochloride in 700 ml of acetic acid under a nitrogen stream, add 25 g of 3,3-dimethyl-2,3-dihydro-1H-inden-1-one, and then at room temperature for 1 hour. After stirring, the mixture was stirred under reflux for 12 hours. After cooling to room temperature, acetic acid was concentrated and the resulting solid was filtered and recrystallized from MC and hexane to obtain 31.53 g of Intermediate 1-1 (yield 52%).

중간체 1-2의 합성Synthesis of Intermediate 1-2

Figure pat00088
Figure pat00088

질소 기류 하에서 (3-bromophenyl)hydrazine hydrochloride 25 g을 아세트산 700 ml으로 녹인 후, 여기에 3,3-dimethyl-2,3-dihydro-1H-inden-1-one 25 g을 넣은 후 실온에서 1시간 교반 후 12시간동안 환류 교반하였다. 실온으로 냉각시킨 후, 아세트산을 농축하여 생성된 고체를 필터링한 후 MC와 헥산으로 재결정하여 중간체 1-1 29.71 g (수율 49%)을 얻었다.Dissolve 25 g of (3-bromophenyl)hydrazine hydrochloride in 700 ml of acetic acid under a nitrogen stream, add 25 g of 3,3-dimethyl-2,3-dihydro-1H-inden-1-one, and then at room temperature for 1 hour. After stirring, the mixture was stirred under reflux for 12 hours. After cooling to room temperature, acetic acid was concentrated, the resulting solid was filtered, and then recrystallized from MC and hexane to obtain 29.71 g of Intermediate 1-1 (yield 49%).

목적 화합물 합성을 위해 OP의 준비는 상기 단계를 거쳐 합성하였다.Preparation of OP for synthesizing the target compound was synthesized through the above steps.

일례로 아래 OP1의 합성법을 제시한다.As an example, the synthesis method of OP1 is presented below.

Figure pat00089
Figure pat00089

둥근바닥플라스크에 N-phenylnaphthalen-1-amine 10 g, 1-bromo-4-iodobenzene 18.0 g, t-BuONa 6.5 g, Pd2(dba)3 1.7 g, (t-Bu)3P 2.6 ml를 톨루엔 100 ml에 녹인 후 50 ℃로 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결하였다. 유기층을 EA로 추출하고 감압여과한 후 컬럼정제하여 중간체 OP1 7.6 g (수율 45%)를 얻었다.In a round-bottom flask, 10 g of N-phenylnaphthalen-1-amine, 18.0 g of 1-bromo-4-iodobenzene, 6.5 g of t-BuONa, 1.7 g of Pd 2 (dba) 3 , 2.6 ml of (t-Bu) 3 P were mixed with toluene. It was dissolved in 100 ml and stirred at 50 °C. The reaction was confirmed by TLC, and the reaction was terminated after addition of water. The organic layer was extracted with EA, filtered under reduced pressure, and column purified to obtain 7.6 g (yield 45%) of the intermediate OP1.

상기 OP1 7.5 g bis(pinacolato)diboron 6.62 g, Pd(dppf)Cl2 0.07 g, KOAc 5.9 g을 톨루엔 80 ml에 녹인 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결하였다. 유기층을 EA로 추출하고 감압여과한 후 컬럼정제하여 중간체 OP2 6.8 g (수율 81%)을 얻었다.The OP1 7.5 g bis(pinacolato)diboron 6.62 g, Pd(dppf)Cl 2 0.07 g, and KOAc 5.9 g were dissolved in 80 ml toluene and stirred under reflux. The reaction was confirmed by TLC, and the reaction was terminated after addition of water. The organic layer was extracted with EA, filtered under reduced pressure, and purified by column to obtain 6.8 g of intermediate OP2 (yield 81%).

하기 OP1부터 OP9 중간체는 상기 OP1과 같은 방법으로 합성하였다.The following intermediates OP1 to OP9 were synthesized in the same manner as in OP1.

Figure pat00090
Figure pat00090

화합물 1의 합성Synthesis of compound 1

Figure pat00091
Figure pat00091

둥근바닥플라스크에 중간체 1-1 2.0 g, di([1,1'-biphenyl]-4-yl)amine 2.0 g, t-BuONa 0.74 g, Pd2(dba)3 0.20 g, (t-Bu)3P 0.25 ml를 톨루엔 30 ml에 녹인 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결하였다. 유기층을 EA로 추출하고 감압여과한 후 컬럼정제하여 화합물1 1.90g (수율 59%)를 얻었다.In a round-bottom flask, 2.0 g of Intermediate 1-1, 2.0 g of di([1,1'-biphenyl]-4-yl)amine, 0.74 g of t-BuONa, 0.20 g of Pd 2 (dba) 3 , (t-Bu) 0.25 ml of 3 P was dissolved in 30 ml of toluene and stirred under reflux. The reaction was confirmed by TLC, and the reaction was terminated after addition of water. The organic layer was extracted with EA, filtered under reduced pressure, and purified by column to obtain 1.90 g of Compound 1 (yield 59%).

m/z: 628.29 (100.0%), 629.29 (51.2%), 630.29 (13.0%), 631.30 (2.1%)m/z: 628.29 (100.0%), 629.29 (51.2%), 630.29 (13.0%), 631.30 (2.1%)

화합물 2의 합성Synthesis of compound 2

Figure pat00092
Figure pat00092

di([1,1'-biphenyl]-4-yl)amine을 N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine으로 반응한 것을 제외하고는 화합물 1과 동일한 방법으로 화합물 2를 합성하였다. (수율 63%)di([1,1'-biphenyl]-4-yl)amine was reacted with N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine Compound 2 was synthesized in the same manner as in Compound 1, except that. (Yield 63%)

m/z: 668.32 (100.0%), 669.32 (54.8%), 670.33 (14.6%), 671.33 (2.5%)m/z: 668.32 (100.0%), 669.32 (54.8%), 670.33 (14.6%), 671.33 (2.5%)

화합물 3의 합성Synthesis of compound 3

Figure pat00093
Figure pat00093

둥근바닥플라스크에 중간체 1-1 2.0 g, OP1 2.60 g, 1,4-dioxan 30 ml에 녹이고 K2CO3(2M) 7.7 ml와 Pd(PPh3)4 0.18 g을 넣은 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결시켰다. 유기층을 MC로 추출하고 감압여과한 후 컬럼정제하여 화합물 3 1.83 g (수율 59%)를 얻었다.In a round-bottom flask, 2.0 g of Intermediate 1-1, 2.60 g of OP1, and 30 ml of 1,4-dioxan were dissolved, and 7.7 ml of K 2 CO 3 (2M) and 0.18 g of Pd(PPh 3 ) 4 were added, followed by stirring under reflux. The reaction was confirmed by TLC, and the reaction was terminated after addition of water. The organic layer was extracted with MC, filtered under reduced pressure, and purified by column to obtain 1.83 g of Compound 3 (yield 59%).

m/z: 602.27 (100.0%), 603.28 (49.1%), 604.28 (11.8%), 605.28 (1.9%)m/z: 602.27 (100.0%), 603.28 (49.1%), 604.28 (11.8%), 605.28 (1.9%)

화합물 4의 합성Synthesis of compound 4

Figure pat00094
Figure pat00094

OP1을 OP2로 반응한 것을 제외하고는 화합물 3과 동일한 방법으로 화합물 4를 합성하였다. (수율 60%)Compound 4 was synthesized in the same manner as in Compound 3, except that OP1 was reacted with OP2. (yield 60%)

m/z: 704.32 (100.0%), 705.32 (58.1%), 706.33 (16.4%), 707.33 (3.0%)m/z: 704.32 (100.0%), 705.32 (58.1%), 706.33 (16.4%), 707.33 (3.0%)

화합물 5의 합성Synthesis of compound 5

Figure pat00095
Figure pat00095

OP1을 OP3로 반응한 것을 제외하고는 화합물 3과 동일한 방법으로 화합물 5를 합성하였다. (수율 65%)Compound 5 was synthesized in the same manner as in Compound 3, except that OP1 was reacted with OP3. (Yield 65%)

m/z: 744.35 (100.0%), 745.35 (61.3%), 746.36 (18.3%), 747.36 (3.6%)m/z: 744.35 (100.0%), 745.35 (61.3%), 746.36 (18.3%), 747.36 (3.6%)

화합물 6의 합성Synthesis of compound 6

Figure pat00096
Figure pat00096

OP1을 OP6으로 반응한 것을 제외하고는 화합물 3과 동일한 방법으로 화합물 6을 합성하였다. (수율 58%)Compound 6 was synthesized in the same manner as in Compound 3, except that OP1 was reacted with OP6. (yield 58%)

m/z: 780.35 (100.0%), 781.35 (64.6%), 782.36 (20.3%), 783.36 (4.2%)m/z: 780.35 (100.0%), 781.35 (64.6%), 782.36 (20.3%), 783.36 (4.2%)

화합물 7의 합성Synthesis of compound 7

Figure pat00097
Figure pat00097

OP1을 OP7로 반응한 것을 제외하고는 화합물 3과 동일한 방법으로 화합물 7을 합성하였다. (수율 58%)Compound 7 was synthesized in the same manner as in Compound 3, except that OP1 was reacted with OP7. (yield 58%)

m/z: 820.38 (100.0%), 821.39 (67.6%), 822.39 (22.5%), 823.39 (5.1%)m/z: 820.38 (100.0%), 821.39 (67.6%), 822.39 (22.5%), 823.39 (5.1%)

화합물 8의 합성Synthesis of compound 8

Figure pat00098
Figure pat00098

OP1을 OP8로 반응한 것을 제외하고는 화합물 3과 동일한 방법으로 화합물 8을 합성하였다. (수율 52%)Compound 8 was synthesized in the same manner as in Compound 3, except that OP1 was reacted with OP8. (Yield 52%)

m/z: 704.32 (100.0%), 705.32 (58.1%), 706.33 (16.4%), 707.33 (3.0%)m/z: 704.32 (100.0%), 705.32 (58.1%), 706.33 (16.4%), 707.33 (3.0%)

화합물 9의 합성Synthesis of compound 9

Figure pat00099
Figure pat00099

OP1을 OP9로 반응한 것을 제외하고는 화합물 3과 동일한 방법으로 화합물 9를 합성하였다. (수율 50%)Compound 9 was synthesized in the same manner as in Compound 3, except that OP1 was reacted with OP9. (Yield 50%)

m/z: 744.35 (100.0%), 745.35 (61.3%), 746.36 (18.3%), 747.36 (3.6%)m/z: 744.35 (100.0%), 745.35 (61.3%), 746.36 (18.3%), 747.36 (3.6%)

화합물 10의 합성Synthesis of compound 10

Figure pat00100
Figure pat00100

둥근바닥플라스크에 중간체 1-2 2.0 g, di([1,1'-biphenyl]-4-yl)amine 2.0 g, t-BuONa 0.74 g, Pd2(dba)3 0.20 g, (t-Bu)3P 0.25 ml를 톨루엔 30 ml에 녹인 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결하였다. 유기층을 EA로 추출하고 감압여과한 후 컬럼정제하여 화합물 10을 1.78 g (수율 55%)를 얻었다.Intermediate 1-2 2.0 g, di([1,1'-biphenyl]-4-yl)amine 2.0 g, t-BuONa 0.74 g, Pd 2 (dba) 3 0.20 g, (t-Bu) in a round-bottom flask 0.25 ml of 3 P was dissolved in 30 ml of toluene and stirred under reflux. The reaction was confirmed by TLC, and the reaction was terminated after addition of water. The organic layer was extracted with EA, filtered under reduced pressure, and purified by column to obtain 1.78 g (yield 55%) of compound 10.

화합물 11의 합성Synthesis of compound 11

Figure pat00101
Figure pat00101

di([1,1'-biphenyl]-4-yl)amine을 N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine으로 반응한 것을 제외하고는 화합물 10과 동일한 방법으로 화합물 11을 합성하였다. (수율 55%)di([1,1'-biphenyl]-4-yl)amine was reacted with N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine Compound 11 was synthesized in the same manner as in Compound 10, except that. (Yield 55%)

m/z: 668.32 (100.0%), 669.32 (54.8%), 670.33 (14.6%), 671.33 (2.5%)m/z: 668.32 (100.0%), 669.32 (54.8%), 670.33 (14.6%), 671.33 (2.5%)

화합물 12의 합성Synthesis of compound 12

Figure pat00102
Figure pat00102

둥근바닥플라스크에 중간체 1-2 2.0 g, OP2 3.08 g, 1,4-dioxan 30 ml에 녹이고 K2CO3(2M) 7.7 ml와 Pd(PPh3)4 0.18 g을 넣은 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결시켰다. 유기층을 MC로 추출하고 감압여과한 후 컬럼정제하여 화합물 12를 2.0 g (수율 55%)을 얻었다.In a round bottom flask, 2.0 g of Intermediate 1-2, 3.08 g of OP2, and 30 ml of 1,4-dioxan were dissolved, and 7.7 ml of K 2 CO 3 (2M) and 0.18 g of Pd(PPh 3 ) 4 were added, followed by stirring under reflux. The reaction was confirmed by TLC, and the reaction was terminated after addition of water. The organic layer was extracted with MC, filtered under reduced pressure, and purified by column to obtain 2.0 g (yield 55%) of compound 12.

m/z: 704.32 (100.0%), 705.32 (58.1%), 706.33 (16.4%), 707.33 (3.0%)m/z: 704.32 (100.0%), 705.32 (58.1%), 706.33 (16.4%), 707.33 (3.0%)

화합물 13의 합성Synthesis of compound 13

Figure pat00103
Figure pat00103

OP2를 OP3으로 반응한 것을 제외하고는 화합물 12와 동일한 방법으로 화합물 13을 합성하였다. (수율 52%)Compound 13 was synthesized in the same manner as in Compound 12, except that OP2 was reacted with OP3. (Yield 52%)

m/z: 744.35 (100.0%), 745.35 (61.3%), 746.36 (18.3%), 747.36 (3.6%)m/z: 744.35 (100.0%), 745.35 (61.3%), 746.36 (18.3%), 747.36 (3.6%)

화합물 14의 합성Synthesis of compound 14

Figure pat00104
Figure pat00104

OP2를 OP6으로 반응한 것을 제외하고는 화합물 12와 동일한 방법으로 화합물 14를 합성하였다. (수율 50%)Compound 14 was synthesized in the same manner as in Compound 12, except that OP2 was reacted with OP6. (Yield 50%)

m/z: 780.35 (100.0%), 781.35 (64.6%), 782.36 (20.3%), 783.36 (4.2%)m/z: 780.35 (100.0%), 781.35 (64.6%), 782.36 (20.3%), 783.36 (4.2%)

화합물 15의 합성Synthesis of compound 15

Figure pat00105
Figure pat00105

OP2를 OP7로 반응한 것을 제외하고는 화합물 12와 동일한 방법으로 화합물 15를 합성하였다. (수율 53%)Compound 15 was synthesized in the same manner as in Compound 12, except that OP2 was reacted with OP7. (Yield 53%)

m/z: 820.38 (100.0%), 821.39 (67.6%), 822.39 (22.5%), 823.39 (5.1%)m/z: 820.38 (100.0%), 821.39 (67.6%), 822.39 (22.5%), 823.39 (5.1%)

유기발광소자의 제조Manufacture of organic light emitting device

도 1에 기재된 구조에 따라 유기발광소자를 제조하였다. 유기발광소자는 아래로부터 정공주입전극(11)/정공주입층(12)/정공수송층(13)/발광층(14)/전자전달층(15)/전자주입전극(16) 순으로 적층되어 있다.An organic light emitting diode was manufactured according to the structure shown in FIG. 1 . The organic light emitting device is stacked in the order of the hole injection electrode 11 / hole injection layer 12 / hole transport layer 13 / light emitting layer 14 / electron transport layer 15 / electron injection electrode 16 from the bottom.

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

Figure pat00106
Figure pat00106

유기발광소자의 제조Manufacture of organic light emitting device

실시예 1Example 1

인듐틴옥사이드(ITO)가 1500 Å 두께가 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필알코올, 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 HT01 600 Å, 정공수송층으로 화합물 1 250 Å를 제막하였다. 다음으로 상기 발광층으로 BH01:BD01 5%로 도핑하여 300 Å 제막하였다. 다음으로 전자전달층으로 ET01 : Liq(1:1) 300 Å 제막한 후 Liq 10 Å, 알루미늄(Al) 1000 Å 제막하고, 이 소자를 글로브 박스에서 밀봉(Encapsulation)함으로써 유기발광소자를 제작하였다.A glass substrate coated with indium tin oxide (ITO) having a thickness of 1500 Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic cleaning is performed with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried, transferred to a plasma cleaner, and then the substrate is cleaned using oxygen plasma for 5 minutes. An evaporator) was used to form a hole injection layer HT01 600 Å and Compound 1 250 Å as a hole transport layer. Next, the light emitting layer was doped with 5% BH01:BD01 to form a film of 300 Å. Next, ET01: Liq (1:1) 300 Å was formed as an electron transport layer, Liq 10 Å, and aluminum (Al) 1000 Å were formed into a film, and an organic light emitting device was manufactured by encapsulating the device in a glove box.

실시예 2 내지 실시예 15 Examples 2 to 15

실시예 1과 같은 방법으로 정공주입층 및 정공전달층을 각각 화합물 2 내지 15를 사용하여 제막한 유기발광소자를 제작하였다.In the same manner as in Example 1, an organic light emitting device in which a hole injection layer and a hole transport layer were formed using Compounds 2 to 15, respectively, was manufactured.

비교예 1Comparative Example 1

상기 실시예 1의 정공전달층을 NPB로 사용한 것을 제외하고는 동일한 방법으로 소자를 제작하였다.A device was manufactured in the same manner except that the hole transport layer of Example 1 was used as an NPB.

비교예 2Comparative Example 2

상기 실시예 1의 정공전달층을 Ref.1로 사용한 것을 제외하고는 동일한 방법으로 소자를 제작하였다.A device was manufactured in the same manner except that the hole transport layer of Example 1 was used as Ref.1.

비교예 3Comparative Example 3

상기 실시예 1의 정공전달층을 Ref.2로 사용한 것을 제외하고는 동일한 방법으로 소자를 제작하였다.A device was manufactured in the same manner except that the hole transport layer of Example 1 was used as Ref.2.

비교예 4Comparative Example 4

상기 실시예 1의 정공전달층을 Ref.3으로 사용한 것을 제외하고는 동일한 방법으로 소자를 제작하였다.A device was manufactured in the same manner except that the hole transport layer of Example 1 was used as Ref.3.

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 1에 나타내었다.Electrons and holes are injected by applying voltage with a Kiethley 2400 source measurement unit, and the luminance when light is emitted is measured using a Konica Minolta spectroradiometer (CS-2000). By doing so, the performances of the organic light emitting devices of Examples and Comparative Examples were evaluated by measuring current density and luminance with respect to applied voltage under atmospheric pressure conditions, and the results are shown in Table 1.

[표 1][Table 1]

Figure pat00107
Figure pat00107

상기 표 1에 나타나는 바와 같이 본 발명의 실시예 1 내지 15는 비교예 1 내지 4에 비하여 모든 면에서 물성이 우수함을 확인할 수 있었다. 이는 본 발명의 화학식 1로 표시되는 화합물이 발광층내 전자를 효과적으로 차단할 수 있도록 높은 LUMO를 가지며, 정공주입층으로부터 정공 주입이 원활한 HOMO를 형성하고, 또한 우수한 홀모빌리티로 인해 효율 및 수명 향상에 큰 영향을 준 것으로 파악된다.As shown in Table 1, it was confirmed that Examples 1 to 15 of the present invention had superior physical properties in all aspects compared to Comparative Examples 1 to 4. This has a high LUMO so that the compound represented by Formula 1 of the present invention can effectively block electrons in the light emitting layer, forms a HOMO in which hole injection from the hole injection layer is smooth, and has a great effect on efficiency and lifespan improvement due to excellent hole mobility is believed to have given

Claims (5)

하기 화학식 1로 표시되는 화합물:
[화학식 1]
Figure pat00108

상기 화학식 1에서,
Ar은 각각 독립적으로 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6-50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-50의 헤테로아릴기이고,
R1 및 R2는 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 C6-50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-50의 헤테로아릴기이며, R1 및 R2는 서로 고리를 형성할 수 있으며,
o는 0 내지 3의 정수이고,
p, q는 각각 독립적으로 1 내지 4의 정수이다.
A compound represented by the following formula (1):
[Formula 1]
Figure pat00108

In Formula 1,
Ar is each independently a C 6-50 aryl group substituted with or unsubstituted with deuterium, a halogen, an amino group, a nitrile group, or a nitro group; Or a C 2-50 heteroaryl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group,
R 1 and R 2 are each independently hydrogen; heavy hydrogen; a C 1-30 alkyl group substituted with or unsubstituted with deuterium, a halogen, an amino group, a nitrile group, or a nitro group; C 2-30 alkenyl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C 2-30 alkynyl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; a C 1-30 alkoxy group substituted or unsubstituted with deuterium, a halogen, an amino group, a nitrile group, or a nitro group; C 6-30 aryloxy group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C 6-50 aryl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; Or deuterium, halogen, amino group, nitrile group, nitro group substituted or unsubstituted C 2-50 heteroaryl group, R 1 and R 2 may form a ring with each other,
o is an integer from 0 to 3,
p and q are each independently an integer of 1 to 4.
 제1항에 있어서,
하기 화학식들 중 어느 하나로 표시되는 것을 특징으로 하는 화합물:
Figure pat00109
Figure pat00110
Figure pat00111
Figure pat00112
Figure pat00113
Figure pat00114
Figure pat00115
Figure pat00116
Figure pat00117
Figure pat00118
Figure pat00119
Figure pat00120
Figure pat00121
Figure pat00122
Figure pat00123
Figure pat00124
Figure pat00125
Figure pat00126
Figure pat00127
Figure pat00128
Figure pat00129
Figure pat00130

Figure pat00131
Figure pat00132
Figure pat00133
Figure pat00134
Figure pat00135
Figure pat00136
Figure pat00137
Figure pat00138
Figure pat00139
Figure pat00140
Figure pat00141
Figure pat00142
Figure pat00143
Figure pat00144
Figure pat00145
Figure pat00146
Figure pat00147
Figure pat00148
Figure pat00149
Figure pat00150
Figure pat00151

Figure pat00152
Figure pat00153
Figure pat00154
Figure pat00155
Figure pat00156
Figure pat00157
Figure pat00158
Figure pat00159
Figure pat00160
Figure pat00161
Figure pat00162
Figure pat00163
Figure pat00164
Figure pat00165
Figure pat00166
Figure pat00167
Figure pat00168
Figure pat00169
Figure pat00170
Figure pat00171
Figure pat00172
Figure pat00173
Figure pat00174
Figure pat00175
Figure pat00176
Figure pat00177
Figure pat00178
Figure pat00179
Figure pat00180
Figure pat00181
Figure pat00182
Figure pat00183
Figure pat00184
Figure pat00185
Figure pat00186
Figure pat00187
Figure pat00188
Figure pat00189
Figure pat00190
Figure pat00191
.
According to claim 1,
A compound characterized in that it is represented by any one of the following formulas:
Figure pat00109
Figure pat00110
Figure pat00111
Figure pat00112
Figure pat00113
Figure pat00114
Figure pat00115
Figure pat00116
Figure pat00117
Figure pat00118
Figure pat00119
Figure pat00120
Figure pat00121
Figure pat00122
Figure pat00123
Figure pat00124
Figure pat00125
Figure pat00126
Figure pat00127
Figure pat00128
Figure pat00129
Figure pat00130

Figure pat00131
Figure pat00132
Figure pat00133
Figure pat00134
Figure pat00135
Figure pat00136
Figure pat00137
Figure pat00138
Figure pat00139
Figure pat00140
Figure pat00141
Figure pat00142
Figure pat00143
Figure pat00144
Figure pat00145
Figure pat00146
Figure pat00147
Figure pat00148
Figure pat00149
Figure pat00150
Figure pat00151

Figure pat00152
Figure pat00153
Figure pat00154
Figure pat00155
Figure pat00156
Figure pat00157
Figure pat00158
Figure pat00159
Figure pat00160
Figure pat00161
Figure pat00162
Figure pat00163
Figure pat00164
Figure pat00165
Figure pat00166
Figure pat00167
Figure pat00168
Figure pat00169
Figure pat00170
Figure pat00171
Figure pat00172
Figure pat00173
Figure pat00174
Figure pat00175
Figure pat00176
Figure pat00177
Figure pat00178
Figure pat00179
Figure pat00180
Figure pat00181
Figure pat00182
Figure pat00183
Figure pat00184
Figure pat00185
Figure pat00186
Figure pat00187
Figure pat00188
Figure pat00189
Figure pat00190
Figure pat00191
.
 하기 반응식 1로 표시되는 화학식 1의 제조방법:
[반응식 1]
Figure pat00192

상기 반응식에서, 목적화합물은 화학식 1로 표시되는 화합물이며, Ar, R1, R2, o, p, q는 화학식 1에서 정의한 바와 같다.
The preparation method of Formula 1 represented by the following Reaction Scheme 1:
[Scheme 1]
Figure pat00192

In the above scheme, the target compound is a compound represented by Formula 1, and Ar, R 1 , R 2 , o, p, and q are as defined in Formula 1.
 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 at least one organic material layer containing the compound of claim 1 between the two electrodes.
 제4항에 있어서,
상기 유기물층이 정공주입층, 정공수송층 또는 정공수송보조층인 것을 특징으로 하는 유기발광소자.
5. The method of claim 4,
The organic light emitting device, characterized in that the organic layer is a hole injection layer, a hole transport layer or a hole transport auxiliary layer.
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