KR20190143237A - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents
An electroluminescent compound and an electroluminescent device comprising the same Download PDFInfo
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- KR20190143237A KR20190143237A KR1020180070934A KR20180070934A KR20190143237A KR 20190143237 A KR20190143237 A KR 20190143237A KR 1020180070934 A KR1020180070934 A KR 1020180070934A KR 20180070934 A KR20180070934 A KR 20180070934A KR 20190143237 A KR20190143237 A KR 20190143237A
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Abstract
Description
본 발명은 유기발광 화합물에 관한 것으로서, 더욱 상세하게는 유기발광소자의 정공주입층 또는 정공수송층의 정공수송 재료로 채용되는 유기발광 화합물 및 이를 채용하여 저전압 구동이 가능하고, 발광 효율 및 수명 특성이 현저히 향상된 유기발광소자에 관한 것이다.The present invention relates to an organic light emitting compound, and more particularly, an organic light emitting compound that is employed as a hole transporting material of a hole injection layer or a hole transporting layer of an organic light emitting device, and employing the low-voltage driving, light emission efficiency and life characteristics The present invention relates to a significantly improved organic light emitting device.
최근 자체 발광형으로 저전압 구동이 가능한 유기발광소자는 평판 표시 소자의 주류인 액정디스플레이에 비해, 시야각, 대조비 등이 우수하고 백라이트가 불필요하며 경량 및 박형이 가능하고 소비전력 측면에서도 유리하며 색 재현 범위가 넓어 차세대 표시소자로서 주목받고 있다.Recently, the organic light emitting device capable of low-voltage driving by self-emission type has better viewing angle, contrast ratio, etc., does not need backlight, light weight and thinness, is advantageous in terms of power consumption, and color reproduction range compared to the liquid crystal display which is the mainstream of flat panel display devices. It is widely attracting attention as a next generation display device.
유기발광소자는 전자 주입 전극(음극)과 정공 주입 전극(양극) 사이에 형성된 유기 발광층에 전하를 주입하면 전자와 정공이 쌍을 이룬 후 소멸하면서 빛을 내는 소자로서, 플라스틱과 같이 휠 수 있는 투명 기판 위에도 소자를 형성할 수 있을 뿐 아니라, 플라즈마 디스플레이 패널이나 무기발광 디스플레이에 비해 10 V 이하의 낮은 전압에서 구동이 가능하고, 전력 소모가 비교적 적으며, 색감이 뛰어나다는 장점이 있다. 또한, 유기발광소자는 녹색, 청색, 적색의 3 가지 색을 나타낼 수가 있어 차세대 풍부한 색 디스플레이 소자로 많은 관심의 대상이 되고 있다.An organic light emitting device emits light when electrons and holes are paired and extinguished when electric charge is injected into the organic light emitting layer formed between the electron injection electrode (cathode) and the hole injection electrode (anode). In addition to the device can be formed on the substrate, it is possible to drive at a lower voltage of 10V or less than the plasma display panel or the inorganic light emitting display, has the advantage of relatively low power consumption and excellent color. In addition, since the organic light emitting device can display three colors of green, blue, and red, it has been attracting much attention as a next-generation rich color display device.
유기발광소자는 빛을 내기 위한 과정, 즉 전하 주입, 전하 수송, 광 여기자 형성 및 빛의 발생들을 각각 다른 유기층을 이용하여 역할 분담을 시키고 있다. 이에 따라서 양극과 음극 사이에 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등을 포함하며 또는 그 이상의 층으로 세분화된 구조의 유기발광소자가 사용되고 있으며, 유기발광소자가 전술한 특징을 발휘하기 위해서는 소자 내 유기층을 이루는 물질인 정공주입 물질, 정공수송 물질, 발광 물질, 전자수송 물질, 전자주입 물질, 전자저지 물질 등이 안정하고 효율적인 재료에 의하여 뒷받침되는 것이 선행되어야 하나, 아직까지는 안정하고 효율적인 유기발광소자용 유기물층 재료의 개발이 충분히 이루어지지 않은 상태이다.The organic light emitting device divides the process for emitting light, that is, charge injection, charge transport, photo-exciter formation, and light generation by using different organic layers. Accordingly, an organic light emitting device having a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like divided between the anode and the cathode and having more layers is used, and the organic light emitting device has the aforementioned characteristics. In order to exert, the material that forms the organic layer in the device must be preceded by a stable and efficient material such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, an electron blocking material, etc. The development of an efficient organic material layer for an organic light emitting device has not been made sufficiently.
따라서, 더욱 안정적인 유기전계발광소자를 구현하고, 소자의 고효율, 장수명, 대형화 등을 위해서는 효율 및 수명 특성 측면에서 추가적인 개선이 요구되고 있는 상황이고, 이와 관련하여 최근에는 상기 유기발광소자의 구조 중 정공수송층 소재에 대하여는 기존 유기 소재의 도전율(mobility)을 향상시키기 위하여 p-type의 물질을 도핑하거나, 층을 세분화하여 전극과 해당 정공수송층 사이에 p-type 물질을 포함하는 층을 더 구비하는 연구가 이루어지고 있다.Therefore, in order to implement a more stable organic light emitting display device, and to improve the efficiency, long life, and size of the device, further improvement is required in terms of efficiency and lifespan. In this regard, in recent years, holes in the structure of the organic light emitting device are required. For the transport layer material, in order to improve the mobility (mobility) of the existing organic material, a researcher further comprising a layer containing a p-type material between the electrode and the hole transport layer by doping the p-type material or by subdividing the layer. It is done.
특히, 유기물을 도핑하면 음성 전도도가 형성되어 두꺼운 수송층이라 할 지라도 수송층에서의 전압 강하를 낮출 수 있고, 도핑 준위를 높임으로 인해 형성된 얇은 공간 전하층은 터널링에 의한 전하 주입을 효과적으로 할 수 있도록 해준다. 정공 수송층에 도핑을 함으로써 정공 수송층의 높은 전도도와 전하 운반자의 전하 밀도를 제어할 수 있고, 결국 유기물층의 전도도가 향상되어 소자의 특성이 향상되어 낮은 구동 전압과 고효율의 소자를 구현할 수 있다.In particular, when the organic material is doped, negative conductivity is formed, and even a thick transport layer can lower the voltage drop in the transport layer, and the thin space charge layer formed by increasing the doping level can effectively inject the charge by tunneling. By doping the hole transport layer, it is possible to control the high conductivity of the hole transport layer and the charge density of the charge carriers. Consequently, the conductivity of the organic material layer is improved to improve the characteristics of the device, thereby realizing a low driving voltage and a high efficiency device.
그러나, 추가적인 유기소재 및 유기층의 적용에 따른 공정 효율성이 떨어지고, 유기층의 두께 문제 등으로 저전압 구동의 구현이 어려워지는 등의 문제점이 여전히 존재한다.However, there are still problems such as low process efficiency due to the application of additional organic materials and organic layers, and difficulty in implementing low voltage driving due to thickness problems of the organic layers.
따라서, 본 발명은 상기 문제점을 해결하고자 하는 것으로서, 정공수송소재에 대해서 p-doping을 별도로 하지 않고, p-doping과 정공수송과 함께 거둘 수 있는 융합된 물질 구조의 화합물을 제공하고, 이를 도입하여 향상된 발광효율과 장수명 등의 특성을 안정적으로 구현하면서 종래 소자와 동등 또는 그 이상의 수준으로 저전압 구동을 구현할 수 있는 유기발광소자를 제공하고자 한다.Accordingly, the present invention is to solve the above problems, without providing a separate p-doping for the hole transport material, providing a compound of a fused material structure that can be harvested with p-doping and hole transport, and introduced by The present invention is to provide an organic light emitting device capable of stably implementing characteristics such as improved luminous efficiency and long life while driving low voltage at a level equal to or higher than that of a conventional device.
본 발명은 상기 과제를 해결하기 위하여, 하기 [화학식 Ⅰ] 또는 [화학식 Ⅱ]로 표시되고, p-doping 기능과 정공수송 특성을 갖는 각각의 모이어티(moiety)를 하나의 구조에 도입한 유기발광 화합물과 [화학식 Ⅰ] 또는 [화학식 Ⅱ]로 표시되는 1종 이상의 발광 화합물을 유기층 내에 포함하는 유기발광소자를 제공한다.In order to solve the above problems, the present invention is represented by the following [Formula I] or [Formula II], the organic light-emitting of each moiety (moiety) having a p-doping function and hole transport characteristics in one structure Provided is an organic light emitting device comprising a compound and at least one light emitting compound represented by [Formula I] or [Formula II] in an organic layer.
[화학식 Ⅰ][Formula I]
[화학식 Ⅱ][Formula II]
상기 [화학식 Ⅰ] 또는 [화학식 Ⅱ]의 구조 및 치환기에 대해서는 후술하기로 한다.The structure and substituents of the above [Formula I] or [Formula II] will be described later.
본 발명에 따른 유기발광 화합물은 p-도핑(doping) 기능과 정공수송 특성 하나로 융합한 것을 특징으로 하여, 이를 도입한 소자는 종래 소자에 비하여 별도의 p-도핑을 하지 않고도 정공수송도를 향상시키고 그에 따라 향상된 발광효율과 종래 소자 대비 동등한 수준 이상의 저전압 구동을 구현할 수 있어 다양한 디스플레이 소자에 유용하게 활용할 수 있으며, 종래 소자 대비 별도의 p-type 층을 구비하는 공정이나, p-doping 공정이 요구되지 않아 소자 제조 공정 효율성도 향상시킬 수 있다.The organic light emitting compound according to the present invention is characterized in that the fusion with one of the p-doping (hole) function and hole transport characteristics, the device introduced this improves the hole transportability without a separate p-doping compared to the conventional device As a result, it is possible to realize improved luminous efficiency and low voltage driving equivalent to that of conventional devices, which can be usefully used for various display devices, and a process having a separate p-type layer or a p-doping process is not required. As a result, device manufacturing process efficiency can be improved.
도 1은 본 발명에 따른 유기발광 화합물의 구조를 나타낸 대표도이다.1 is a representative view showing the structure of an organic light emitting compound according to the present invention.
이하, 본 발명을 더욱 상세하게 설명한다.Hereinafter, the present invention will be described in more detail.
본 발명은 p-도핑(doping) 기능과 정공수송 특성을 갖는 각각의 모이어티(moiety)를 하나의 구조에 도입하여 별도의 p-도핑을 하지 않고도 소자의 저전압 구동 특성을 구현하고 정공수송도가 우수하여 소자의 향상된 발광효율을 거둘 수 있는 하기 [화학식 Ⅰ] 또는 [화학식 Ⅱ]로 표시되는 유기발광 화합물에 관한 것이다.According to the present invention, each moiety having a p-doping function and a hole transport characteristic is introduced into a structure to realize low voltage driving characteristics of the device without additional p-doping, and a hole transport diagram. The present invention relates to an organic light emitting compound represented by the following [Formula I] or [Formula II] capable of achieving an improved luminous efficiency of the device.
[화학식 Ⅰ][Formula I]
[화학식 Ⅱ][Formula II]
상기 [화학식 Ⅰ] 또는 [화학식 Ⅱ]에서,In [Formula I] or [Formula II],
R1 내지 R4는 각각 독립적으로 시아노기(CN), 니트로기(NO2), 할로겐기, 설포닐기(SO2R'), 설폭사이드기(SO3), 카르보닐기(COR') 또는 카르복실기(CO2R')이거나, 이들 중에서 선택되는 하나 이상이 치환된 탄소수 6 내지 30의 아릴기이거나 탄수소 2 내지 30의 헤테로아릴기일 수 있으며, 상기 R'은 수소, 중수소, 시아노기, 할로겐기, 아미노기, 싸이올기, 히드록시기, 니트로기, 탄소수 1 내지 24의 알킬기, 탄소수 1 내지 24의 할로겐화된 알킬기, 탄소수 2 내지 24의 알케닐기, 탄소수 6 내지 24의 아릴기, 탄소수 2 내지 24의 헤테로아릴기, 탄소수 1 내기 24의 알콕시기, 탄소수 1 내지 24의 알킬실릴기 및 탄소수 1 내지 24의 아릴실릴기 중에서 선택된다.R 1 to R 4 are each independently a cyano group (CN), a nitro group (NO 2 ), a halogen group, a sulfonyl group (SO 2 R '), a sulfoxide group (SO 3 ), a carbonyl group (COR'), or a carboxyl group ( CO 2 R '), or one or more selected from them may be substituted aryl group having 6 to 30 carbon atoms or heteroaryl group having 2 to 30 carbon atoms, wherein R' is hydrogen, deuterium, cyano group, halogen group, Amino group, thiol group, hydroxy group, nitro group, alkyl group of 1 to 24 carbon atoms, halogenated alkyl group of 1 to 24 carbon atoms, alkenyl group of 2 to 24 carbon atoms, aryl group of 6 to 24 carbon atoms, heteroaryl group of 2 to 24 carbon atoms , An alkoxy group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, and an arylsilyl group having 1 to 24 carbon atoms.
R9 내지 R16은 각각 독립적으로 수소, 중수소 또는 할로겐기이다.R 9 to R 16 are each independently hydrogen, deuterium or a halogen group.
R5 내지 R8은 각각 수소, 시아노기, 할로겐기, 아미노기, 싸이올기, 히드록시기, 니트로기, 치환 또는 비치환된 탄소수 1 내지 24의 알킬기, 치환 또는 비치환된 탄소수 1 내지 24의 할로겐화된 알킬기, 치환 또는 비치환된 탄소수 2 내지 24의 알케닐기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 치환 또는 비치환된 탄소수 2 내지 30의 헤테로아릴기, 치환 또는 비치환된 탄소수 1 내기 24의 알콕시기, 치환 또는 비치환된 탄소수 1 내지 24의 알킬실릴기, 탄소수 6 내지 30의 아릴실릴기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴아민기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기 및 치환 또는 비치환된 탄소수 6 내지 30의 아릴싸이오기 중에서 선택된다.R 5 to R 8 are each hydrogen, cyano group, halogen group, amino group, thiol group, hydroxy group, nitro group, substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, substituted or unsubstituted halogenated alkyl group having 1 to 24 carbon atoms, respectively. , Substituted or unsubstituted alkenyl group having 2 to 24 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon atoms 1 to 24 An alkoxy group, a substituted or unsubstituted C1-C24 alkylsilyl group, a C6-C30 arylsilyl group, a substituted or unsubstituted C6-C30 arylamine group, a substituted or unsubstituted C6-C30 Is selected from an aryloxy group and a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms.
또한, 본 발명의 일 실시예에 의하면, 상기 R5 내지 R6 중 적어도 어느 하나 및 R7 내지 R8 중 적어도 어느 하나는 하기 [구조식 1]과 [구조식 2] 중에서 선택되는 어느 하나일 수 있으며, 이러한 특징으로 갖는 구조는 후술하는 구체적인 화합물에서 이를 확인할 수 있다.In addition, according to an embodiment of the present invention, at least one of the R 5 to R 6 and at least one of R 7 to R 8 may be any one selected from the following [formula 1] and [formula 2] , The structure having such a feature can be confirmed in the specific compound described below.
[구조식 1][Formula 1]
[구조식 2][Formula 2]
상기 [구조식 1]과 [구조식 2]에서,In [Formula 1] and [Formula 2],
L1 및 L2는 각각 단일결합이거나, 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기 및 치환 또는 비치환된 탄소수 2 내지 30의 헤테로아릴렌기 중에서 선택되고, n 및 m은 각각 1 내지 4의 정수이며, n 및 m은 각각 2 이상인 경우, 복수 개의 L1 및 L2는 각각 서로 동일하거나 상이할 수 있다.L 1 and L 2 are each a single bond or are selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, and n and m are each selected from 1 to 4 When n and m are each 2 or more, a plurality of L 1 and L 2 may be the same or different from each other.
Ar1 내지 Ar3는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 5 내지 50의 아릴기 및 치환 또는 비치환된 탄소수 2 내지 50의 헤테로아릴기 중에서 선택되며, 상기 Ar1 및 Ar2는 서로 결합하거나 인접한 치환기와 연결되어 지환족, 방향족의 단일환 또는 다환 고리를 형성할 수 있으며, 상기 형성된 지환족, 방향족의 단일환 또는 다환 고리의 탄소원자는 N, S 및 O 중에서 선택되는 어느 하나 이상의 헤테로원자로 치환될 수 있다.Ar 1 to Ar 3 are the same as or different from each other, each independently selected from a substituted or unsubstituted aryl group having 5 to 50 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, wherein Ar 1 and Ar 2 may be bonded to each other or connected to an adjacent substituent to form an alicyclic or aromatic monocyclic or polycyclic ring, and the carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring may be selected from N, S and O. It may be substituted with one or more heteroatoms.
o, p 및 q는 각각 1 내지 3이 정수이고, 상기 o, p 및 q가 각각 2 이상인 경우 복수의 Ar1 내지 Ar3는 각각 서로 동일하거나 상이할 수 있다.o, p, and q are each an integer of 1 to 3, and when o, p and q are each 2 or more, a plurality of Ar 1 to Ar 3 may be the same or different from each other.
또한, 상기 R5 내지 R6과, R7 내지 R8은 각각 서로 결합하거나 인접한 치환기와 연결되어 지환족, 방향족의 단일환 또는 다환 고리를 형성할 수 있으며, 상기 형성된 지환족, 방향족의 단일환 또는 다환 고리의 탄소원자는 N, S 및 O 중에서 선택되는 어느 하나 이상의 헤테로원자로 치환될 수 있으며, 본 발명의 일 실시예에 의하면, 하기 [화학식 Ⅰ-1] 내지 [화학식 Ⅰ-2] 및 [화학식 Ⅱ-1] 내지 [화학식 Ⅱ-2] 중에서 선택되는 어느 하나일 수 있다.In addition, R 5 to R 6 and R 7 to R 8 may be bonded to each other or connected to adjacent substituents to form an alicyclic or aromatic monocyclic or polycyclic ring, and the formed alicyclic and aromatic monocyclic rings. Alternatively, the carbon atom of the polycyclic ring may be substituted with any one or more heteroatoms selected from N, S, and O, and according to an embodiment of the present invention, the following [Formula I-1] to [Formula I-2] and [Formula I] II-1] to [Formula II-2].
[화학식 Ⅰ-1] [화학식 Ⅰ-2][Formula I-1] [Formula I-2]
[화학식 Ⅱ-1] [화학식 Ⅱ-2][Formula II-1] [Formula II-2]
상기 [화학식 Ⅰ-1] 내지 [화학식 Ⅰ-2] 및 [화학식 Ⅱ-1] 내지 [화학식 Ⅱ-2]에서, R1 내지 R4 및 R9 내지 R16은 각각 상기 [화학식 Ⅰ] 또는 [화학식 Ⅱ]에서의 정의와 동일하고, R17 내지 R24는 각각 수소, 중수소, 시아노기, 할로겐기, 아미노기, 싸이올기, 히드록시기, 니트로기 및 탄소수 1 내지 24의 할로겐화된 알킬기 중에서 선택되는 어느 하나이고, X는 O, S, -N-Ra 또는 -Ra-C-Rb- (상기 Ra 및 Rb는 각각 수소 또는 메틸기임)이다.In [Formula I-1] to [Formula I-2] and [Formula II-1] to [Formula II-2], R 1 to R 4 and R 9 to R 16 are each represented by [Formula I] or [ Is the same as defined in formula (II), and R 17 to R 24 are each selected from hydrogen, deuterium, cyano group, halogen group, amino group, thiol group, hydroxy group, nitro group and halogenated alkyl group having 1 to 24 carbon atoms And X is O, S, -N-Ra or -Ra-C-Rb-, wherein Ra and Rb are each hydrogen or a methyl group.
한편, 상기 치환 또는 비치환된이라 함은, 상기 R5 내지 R8, L 및 Ar1 내지 Ar3가 각각 1종 이상의 치환기로 더 치환될 수 있는 것을 의미하는 것으로서, 상기 1종 이상의 치환기는 중수소, 시아노기, 할로겐기, 아미노기, 싸이올기, 히드록시기, 니트로기, 탄소수 1 내지 24의 알킬기, 탄소수 1 내지 24의 할로겐화된 알킬기, 탄소수 2 내지 24의 알케닐기, 탄소수 6 내지 24의 아릴기, 탄소수 2 내지 24의 헤테로아릴기, 탄소수 1 내기 24의 알콕시기, 탄소수 1 내지 24의 탄소수 1 내지 24의 알킬실릴기 및 탄소수 1 내지 24의 아릴실릴기로 이루어진 군에서 선택된다.Meanwhile, the substituted or unsubstituted means that R 5 to R 8 , L and Ar 1 to Ar 3 may each be further substituted with one or more substituents, and the one or more substituents may be deuterium. , Cyano group, halogen group, amino group, thiol group, hydroxy group, nitro group, C1-C24 alkyl group, C1-C24 halogenated alkyl group, C2-C24 alkenyl group, C6-C24 aryl group, carbon number It is selected from the group consisting of a heteroaryl group of 2 to 24, an alkoxy group of 1 to 24 carbon atoms, an alkylsilyl group of 1 to 24 carbon atoms and an arylsilyl group of 1 to 24 carbon atoms.
본 발명에 있어서, 상기 치환기들의 예시들에 대해서 구체적으로 설명하면 아래와 같으나, 이에 한정되는 것은 아니다.In the present invention, examples of the substituents will be described in detail below, but is not limited thereto.
본 발명에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 구체적인 예로는 메틸기, 에틸기, 프로필기, n-프로필기, 이소프로필기, 부틸기, n-부틸기, 이소부틸기, tert-부틸기, sec-부틸기, 1-메틸-부틸기, 1-에틸-부틸기, 펜틸기, n-펜틸기, 이소펜틸기, 네오펜틸기, tert-펜틸기, 헥실기, n-헥실기, 1-메틸펜틸기, 2-메틸펜틸기 등이 있으나, 이들에 한정되지 않는다.In the present invention, the alkyl group may be linear or branched chain, specific examples are methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group , sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1 -Methylpentyl group, 2-methylpentyl group and the like, but are not limited thereto.
본 발명에 있어서, 아릴기는 단환식 또는 다환식일 수 있고, 단환식 아릴기의 예로는 페닐기, 비페닐기, 터페닐기, 스틸벤기 등이 있고, 다환식 아릴기의 예로는 나프틸기, 안트라세닐기, 페난트레닐기, 파이레닐기, 페릴레닐기, 테트라세닐기, 크라이세닐기, 플루오레닐기, 아세나프타센닐기, 트리페닐렌기, 플루오안트렌(fluoranthrene)기 등이 있으나, 본 발명의 범위가 이들 예로만 한정되는 것은 아니다.In the present invention, the aryl group may be monocyclic or polycyclic, and examples of the monocyclic aryl group include phenyl group, biphenyl group, terphenyl group, stilbene group, and the like, and examples of the polycyclic aryl group include naphthyl group and anthracenyl group. , Phenanthrenyl group, pyrenyl group, peryllenyl group, tetrasenyl group, chrysenyl group, fluorenyl group, acenaphthacenyl group, triphenylene group, fluoranthrene group, etc., but the scope of the present invention It is not limited only to these examples.
본 발명에 있어서, 헤테로아릴기는 이종원자로 O, N 또는 S를 포함하는 헤테로고리기로서, 헤테로고리기의 예로는 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기, 트리아졸기, 아크리딜기, 피리다진기, 피라지닐기, 퀴놀리닐기, 퀴나졸린기, 퀴녹살리닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤조옥사졸기, 벤조이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 디벤조퓨라닐기, 페난트롤린기, 티아졸릴기, 이소옥사졸릴기, 옥사디아졸릴기, 티아디아졸릴기, 벤조티아졸릴기, 페노티아지닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present invention, the heteroaryl group is a heterocyclic group containing O, N or S as a hetero atom, and examples of the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group and oxa Diazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, acridil group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl Group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene Group, dibenzothiophene group, benzofuranyl group, dibenzofuranyl group, phenanthroline group, thiazolyl group, isooxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, etc. There is, but is not limited to these.
본 발명에 있어서, 아릴싸이오기, 아릴아민기, 아릴실릴기, 아릴옥시기 중의 아릴기는 전술한 아릴기의 예시와 같다.In the present invention, the aryl group in the arylthio group, arylamine group, arylsilyl group, and aryloxy group is the same as the examples of the aryl group described above.
본 발명에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.In the present invention, examples of the halogen group include fluorine, chlorine, bromine or iodine.
본 발명에 있어서, 아릴아민기의 예로는 치환 또는 비치환된 모노아릴아민기, 치환 또는 비치환된 디아릴아민기, 또는 치환 또는 비치환된 트리아릴아민기가 있다. 상기 아릴아민기 중의 아릴기는 단환식 아릴기일 수 있고, 다환식 아릴기일 수 있다. 상기 아릴기가 2 이상을 포함하는 아릴아민기는 단환식 아릴기, 다환식 아릴기, 또는 단환식아릴기와 다환식 아릴기를 동시에 포함할 수 있다.In the present invention, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group, may be a polycyclic aryl group. The arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
상기 아릴아민기의 구체적인 예로는 페닐아민기, 나프틸아민기, 비페닐아민기, 안트라세닐아민기, 3-메틸-페닐아민기, 4-메틸-나프틸아민기, 2-메틸-비페닐아민기, 9-메틸-안트라세닐아민기, 디페닐 아민기, 페닐 나프틸 아민기, 디톨릴 아민기, 페닐 톨릴 아민기, 카바졸기 및 트리페닐 아민기 등이 있으나, 이에 한정되는 것은 아니다.Specific examples of the arylamine group include phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 3-methyl-phenylamine group, 4-methyl-naphthylamine group, 2-methyl-biphenyl Amine groups, 9-methyl-anthracenylamine groups, diphenyl amine groups, phenyl naphthyl amine groups, ditolyl amine groups, phenyl tolyl amine groups, carbazole groups, and triphenyl amine groups, but are not limited thereto.
본 발명에 있어서, 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다.In the present invention, specifically, the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group and the like. However, the present invention is not limited thereto.
본 발명에서 사용되는 치환기인 알콕시기의 구체적인 예로는 메톡시, 에톡, 프로폭시, 이소부틸옥시, sec-부틸옥시, 펜틸옥시, iso-아밀옥시, 헥실옥시 등을 들 수 있고, 상기 알콕시기 중 하나 이상의 수소 원자는 상기 아릴기의 경우와 마찬가지의 치환기로 치환가능하다.Specific examples of the alkoxy group which is a substituent used in the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy and the like. At least one hydrogen atom may be substituted with the same substituent as in the case of the aryl group.
본 발명에서 사용되는 치환기인 할로겐기의 구체적인 예로는 플루오르(F), 클로린(Cl), 브롬(Br) 등을 들 수 있다.Specific examples of the halogen group which is a substituent used in the present invention include fluorine (F), chlorine (Cl), bromine (Br) and the like.
본 발명에서 사용되는 알케닐기의 구체적인 예로는 직쇄상 또는 분지쇄상의 알케닐기를 나타내고, 3-펜테닐기, 4-헥세닐기, 5-헵테닐기, 4-메틸-3-펜테닐기, 2,4-디메틸-펜테닐기, 6-메틸-5-헵테닐기, 2,6-디메틸-5-헵테닐기 등을 들 수 있다.Specific examples of the alkenyl group used in the present invention represent a linear or branched alkenyl group, 3-pentenyl group, 4-hexenyl group, 5-heptenyl group, 4-methyl-3-pentenyl group, 2,4 -Dimethyl-pentenyl group, 6-methyl-5-heptenyl group, 2,6-dimethyl-5-heptenyl group, etc. are mentioned.
상기 [화학식 Ⅰ] 또는 [화학식 Ⅱ]로 표시되는 본 발명에 따른 유기발광 화합물은 그 구조적 특이성으로 인하여 유기발광소자의 유기물층으로 사용될 수 있고, 보다 구체적으로 유기물층 내 정공수송 재료로 사용될 수 있다.The organic light emitting compound according to the present invention represented by the above [Formula I] or [Formula II] may be used as an organic material layer of the organic light emitting device due to its structural specificity, and more specifically may be used as a hole transport material in the organic material layer.
특히, 종래에는 ITO 기판 위에 형성되는 정공수송층의 높은 전도도와 전하 운반자의 전하 밀도를 제어하기 위하여 p-형 도판트를 이용하여 도핑하거나, 또는 ITO 기판과 정공수송층 사이에 p-형 도판트로 이루어진 층을 더 삽입하였으나, 본 발명에서는 별도의 p-형 도판트 공정이나 삽입이 없이 상기 [화학식 Ⅰ] 또는 [화학식 Ⅱ]로 표시되는 화합물로 이루어진 단일 정공수송층을 적용할 수 있다.Particularly, in the related art, a layer of doping using a p-type dopant or a p-type dopant between the ITO substrate and the hole transport layer is used to control the high conductivity of the hole transport layer formed on the ITO substrate and the charge density of the charge carrier. However, in the present invention, a single hole transport layer made of a compound represented by the above [Formula I] or [Formula II] may be applied without a separate p-type dopant process or insertion.
본 발명에 따른 [화학식 Ⅰ] 또는 [화학식 Ⅱ]로 표시되는 유기발광 화합물의 바람직한 구체예로는 하기 화합물들이 있으나, 이들에만 한정되는 것은 아니다.Preferred specific examples of the organic light emitting compound represented by [Formula I] or [Formula II] according to the present invention include the following compounds, but are not limited thereto.
이와 같이, 본 발명에 따른 유기발광 화합물은 p-도핑(doping) 기능과 정공수송 특성을 갖는 각각의 모이어티(moiety)를 하나의 구조에 도입하여 각각 도입된 치환기의 고유 특성을 갖는 유기발광 화합물을 합성할 수 있고, 그 결과 본 발명에 따른 유기발광 화합물을 정공수송층 물질로 적용할 경우 소자의 저전압 구동 특성, 발광효율 및 수명 특성을 더욱 향상시킬 수 있다.As such, the organic light emitting compound according to the present invention introduces each moiety having a p-doping function and a hole transporting property into one structure, and thus an organic light emitting compound having inherent properties of the substituents introduced therein. As a result, when the organic light emitting compound according to the present invention is applied as a hole transport layer material, it is possible to further improve the low voltage driving characteristics, luminous efficiency and lifetime characteristics of the device.
또한, 본 발명의 화합물은 일반적인 유기발광소자 제조방법에 따라 소자에 적용할 수 있다.In addition, the compound of the present invention can be applied to the device according to the general organic light emitting device manufacturing method.
본 발명의 일 실시예에 따른 유기발광소자는 제1 전극과 제2 전극 및 이 사이에 배치된 유기물층을 포함하는 구조로 이루어질 수 있으며, 본 발명에 따른 유기발광 화합물을 소자의 유기물층에 사용한다는 것을 제외하고는 통상의 소자 제조방법 및 재료를 사용하여 제조될 수 있다.The organic light emitting device according to an embodiment of the present invention may be composed of a structure including a first electrode and a second electrode and an organic material layer disposed therebetween, using the organic light emitting compound according to the invention in the organic material layer of the device Except for the conventional device manufacturing method and materials can be used.
본 발명에 따른 유기발광소자의 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 정공 주입층, 정공 수송층, 발광층, 전자 수송층, 전자 주입층 등을 포함하는 구조를 가질 수 있다. 그러나, 이에 한정되지 않고 더 적은 수, 더 많은 수의 유기물층을 포함할 수도 있다.The organic material layer of the organic light emitting device according to the present invention may have a single layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. However, the present invention is not limited thereto, and may include fewer organic layers.
따라서, 본 발명에 따른 유기발광소자에서, 상기 유기물층은 정공수송층, 또는 정공주입 및 정공수송을 동시에 하는 층 중 1층 이상을 포함할 수 있고, 상기 층들 중 1층 이상이 상기 [화학식 Ⅰ] 또는 [화학식 Ⅱ]로 표시되는 화합물을 포함할 수 있다.Accordingly, in the organic light emitting device according to the present invention, the organic material layer may include at least one layer of a hole transport layer, or a layer for simultaneously injecting holes and transporting holes, wherein at least one of the layers is the above [Formula I] or It may include a compound represented by [Formula II].
본 발명에 따른 바람직한 유기발광소자의 유기물층 구조 등에 대해서는 후술하는 실시예에서 보다 상세하게 설명한다.The organic material layer structure and the like of the preferred organic light emitting device according to the present invention will be described in more detail in the following examples.
또한, 본 발명에 따른 유기발광소자는 스퍼터링 (sputtering)이나 전자빔 증발 (e-beam evaporation)과 같은 PVD (physical vapor deposition) 방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공 주입층, 정공 수송층, 발광층, 전자 수송층을 포함하는 유기물층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다.In addition, the organic light emitting device according to the present invention using a metal vapor deposition (PVD) method such as sputtering (e-beam evaporation), metal or conductive metal oxides or alloys thereof on the substrate It can be prepared by depositing an anode to form an anode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물층, 양극 물질을 차례로 증착시켜 유기발광소자를 만들 수도 있다. 상기 유기물층은 정공 주입층, 정공 수송층, 발광층 및 전자 수송층 등을 포함하는 다층 구조일 수도 있으나, 이에 한정되지 않고 단층 구조일 수 있다. 또한, 상기 유기물층은 다양한 고분자 소재를 사용하여 증착법이 아닌 솔벤트 프로세스(solvent process), 예컨대 스핀 코팅, 딥 코팅, 닥터 블레이딩, 스크린 프린팅, 잉크젯 프린팅 또는 열 전사법 등의 방법에 의하여 더 적은 수의 층으로 제조할 수 있다.In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate. The organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. In addition, the organic material layer may be formed by using a variety of polymer materials, and by using a process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, rather than a deposition method. It can be prepared in layers.
상기 양극 물질로는 통상 유기물층으로 정공주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 본 발명에서 사용될 수 있는 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금, 아연 산화물, 인듐 산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물, ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.As the cathode material, a material having a large work function is usually preferred to facilitate hole injection into the organic material layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO) Metal oxides, combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT) Conductive polymers such as polypyrrole and polyaniline, but are not limited thereto.
상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금, LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다.It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof, multilayer such as LiF / Al or LiO 2 / Al. Structural materials and the like, but are not limited thereto.
정공 주입 물질로는 낮은 전압에서 양극으로부터 정공을 잘 주입받을 수 있는 물질로서, 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린(porphyrine), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴 헥사아자트리페닐렌, 퀴나크리돈(quinacridone) 계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.The hole injection material is a material capable of well injecting holes from the anode at a low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene, quinacridone-based organics, perylene-based organics, Anthraquinone, polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
정공수송물질로는 양극이나 정공 주입층으로부터 정공을 수송 받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 본 발명에 따른 유기발광 화합물을 이용하여 소자의 저전압 구동 특성, 발광효율 및 수명 특성을 더욱 향상시킬 수 있다.As a hole transport material, a material capable of transporting holes from an anode or a hole injection layer to be transferred to a light emitting layer is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion, but the low-voltage driving characteristics, the luminous efficiency, and the lifetime characteristics of the device using the organic light emitting compound according to the present invention. Can be further improved.
발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자효율이 좋은 물질이 바람직하다. 구체적인 예로는 8-히드록시-퀴놀린 알루미늄 착물(Alq3), 카르바졸 계열 화합물, 이량체화 스티릴(dimerized styryl) 화합물, BAlq, 10-히드록시벤조 퀴놀린-금속 화합물, 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물, 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자, 스피로(spiro) 화합물, 폴리플루오렌, 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다.The light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxyquinoline aluminum complex (Alq 3 ), carbazole series compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazoles, benzthiazoles and Benzimidazole-based compounds, poly (p-phenylenevinylene) (PPV) -based polymers, spiro compounds, polyfluorenes, rubrene, and the like, but are not limited thereto.
전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 Al 착물, Alq3를 포함한 착물, 유기 라디칼 화합물, 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다.As the electron transporting material, a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer is suitable. Specific examples include Al complexes of 8-hydroxyquinoline, complexes including Alq 3 , organic radical compounds, hydroxyflavone-metal complexes, and the like, but are not limited thereto.
본 발명에 따른 유기발광소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type according to the material used.
또한, 본 발명에 따른 유기발광 화합물은 유기 태양 전지, 유기 감광체, 유기 트랜지스터 등을 비롯한 유기 전자 소자에서도 유기발광소자에 적용되는 것과 유사한 원리로 작용할 수 있다.In addition, the organic light emitting compound according to the present invention may act on a similar principle to that applied to organic light emitting devices in organic electronic devices including organic solar cells, organic photoconductors, organic transistors, and the like.
이하, 바람직한 실시예를 들어 본 발명을 더욱 상세하게 설명한다. 그러나, 이들 실시예는 본 발명을 보다 구체적으로 설명하기 위한 것으로, 본 발명의 범위가 이에 의하여 제한되지 않고, 본 발명의 범주 및 기술사상 범위 내에서 다양한 변경 및 수정이 가능함은 당업계의 통상의 지식을 가진 자에게 자명할 것이다.Hereinafter, the present invention will be described in more detail with reference to preferred examples. However, these examples are intended to illustrate the present invention in more detail, and the scope of the present invention is not limited thereto, and various changes and modifications are possible within the scope and spirit of the present invention. It will be self-evident to those who have knowledge.
합성예Synthesis Example 1 : 화합물 1 합성 1: compound 1 synthesis
(1) (One) 제조예Production Example 1 : 중간체 1-1의 합성 1: Synthesis of Intermediate 1-1
1,2,5,6-Tetraaminonaphthalene (10 g, 0.053 mol, Mascot.), N-Bromosuccinimide (19.86 g, 0.111 mol, sigma aldrich), Dimethylformamide 200 mL 넣고 60 ℃에서 12시간 동안 교반하여 반응시켰다. 반응 종료 후 1 M NaOH 수용액을 넣고 교반시켜 여과한 후 건조하여 <중간체 1-1>을 15 g (수율 81.6%) 수득하였다.1,2,5,6-Tetraaminonaphthalene (10 g, 0.053 mol, Mascot.), N-Bromosuccinimide (19.86 g, 0.111 mol, sigma aldrich) and 200 mL of Dimethylformamide were added and stirred at 60 ° C. for 12 hours. After completion of the reaction, 1M NaOH aqueous solution was added, stirred, filtered, and dried to obtain 15 g (yield 81.6%) of <Intermediate 1-1>.
(2) (2) 제조예Production Example 2 : 중간체 1-2의 합성 2: synthesis of intermediate 1-2
중간체 1-1 (10 g, 0.029 mol), 1,1′carbonyldiimidazole (10.31 g, 0.063 mol, sigma aldrich), DMF 200 mL 넣고 상온에서 24시간 동안 교반하여 반응시켰다. 반응 종료 후 추출한 후 재결정하여 <중간체 1-2>를 9 g (수율 78.2%) 수득하였다.Intermediate 1-1 (10 g, 0.029 mol), 1,1′carbonyldiimidazole (10.31 g, 0.063 mol, sigma aldrich) and 200 mL of DMF were added and reacted at room temperature for 24 hours. After the completion of the reaction, the mixture was extracted and recrystallized to obtain 9 g (yield 78.2%) of <intermediate 1-2>.
(3) (3) 제조예Production Example 3 : 중간체 1-3의 합성 3: Synthesis of Intermediate 1-3
중간체 1-2 (10 g, 0.025 mol), 과량의 MnO2, methylene chloride 150 mL를 넣고 환류 교반하여 24시간 동안 교반하여 반응시켰다. 반응 종료 후 추출한 후 컬럼정제하여 <중간체 1-3>을 8.3 g (수율 83.8%) 수득하였다.Intermediate 1-2 (10 g, 0.025 mol), excess MnO 2 and 150 mL of methylene chloride were added thereto, and the mixture was stirred under reflux for 24 hours to react. After the completion of the reaction, the mixture was extracted and purified by column to obtain 8.3 g (83.8%) of <Intermediate 1-3>.
(4) (4) 제조예Production Example 4 : 중간체 1-4의 합성 4: Synthesis of Intermediate 1-4
중간체 1-3 (10 g, 0.025 mol), malononitrile (5.03 g, 0.076 mol, sigma aldrich), methylene chloride 300 mL 넣고 ice-bath 상태에서 냉각시킨 후 TiCl4 (14.44 g, 0.076 mol, sigma aldrich)를 천천히 떨어드리고 pyridine (12.05 g, 0.152 mol)을 매우 천천히 적가한 후 1시간 후 ice-bath 제거하고 24시간 동안 교반하여 반응시켰다. 반응 종료 후 염산 수용액으로 추출 후 컬럼정제하여 <중간체 1-4>를 9.8 g (수율 78.7%) 수득하였다.Intermediate 1-3 (10 g, 0.025 mol), malononitrile (5.03 g, 0.076 mol, sigma aldrich), 300 mL of methylene chloride and cooled in an ice-bath followed by TiCl 4 (14.44 g, 0.076 mol, sigma aldrich) was slowly dropped and pyridine (12.05 g, 0.152 mol) was added dropwise very slowly. After 1 hour, the ice-bath was removed and the reaction was stirred for 24 hours. After completion of the reaction, the mixture was extracted with an aqueous hydrochloric acid solution and then column purified to obtain 9.8 g (yield 78.7%) of <Intermediate 1-4>.
(5) (5) 제조예Production Example 5 : 화합물 1의 합성 5: synthesis of compound 1
중간체 1-4 (10 g, 0.020 mol), diphenylamine (7.6 g, 0.045 mol, sigma aldrich), Sodium tert-butoxide (7.84 g, 0.081 mol, sigma aldrich), 촉매 Pd(dba)2 (0.59 g, 0.001 mol, sigma aldrich), tri-tert-Bu-phosphine (0.41 g, 0.002 mol, sigma aldrich)에 Toluene 150 mL를 넣고 100 ℃에서 5시간 동안 교반하여 반응시켰다. 반응 종료 후 추출한 후 컬럼 정제하여 화합물 1을 10.5 g (수율 77.1%) 수득하였다.Intermediate 1-4 (10 g, 0.020 mol), diphenylamine (7.6 g, 0.045 mol, sigma aldrich), Sodium tert-butoxide (7.84 g, 0.081 mol, sigma aldrich), catalyst Pd (dba) 2 (0.59 g, 0.001 mol, sigma aldrich) and tri-tert-Bu-phosphine (0.41 g, 0.002 mol, sigma aldrich) were added 150 mL of Toluene and stirred at 100 ° C. for 5 hours. After completion of the reaction, the mixture was extracted and purified by column to obtain 10.5 g (yield 77.1%) of compound 1.
H-NMR (200MHz, CDCl3):δppm, 2H(8.79/s) 4H(6.81/m) 8H(7.20/m, 6.29/d)H-NMR (200 MHz, CDCl 3): δ ppm, 2H (8.79 / s) 4H (6.81 / m) 8H (7.20 / m, 6.29 / d)
LC/MS: m/z=666[(M+1)+]LC / MS: m / z = 666 [(M + 1) + ]
합성예Synthesis Example 2 : 화합물 18 합성 2: Synthesis of Compound 18
(1) (One) 제조예Production Example 1 : 중간체 18-1의 합성 1: Synthesis of Intermediate 18-1
1-bromo-2,3,4,5,6-pentafluorobenzene (10 g, 0.040 mol, sigma aldrich), aniline (4.15 g, 0.044 mol, sigma aldrich), Sodium tert-butoxide (7.78 g, 0.081 mol, sigma aldrich), 촉매 Pd(dba)2 (1.16 g, 0.002 mol, sigma aldrich), tri-tert-Bu-phosphine (0.82 g, 0.004 mol, sigma aldrich)에 Toluene 150 mL를 넣고 100 ℃에서 5시간 동안 교반하여 반응시켰다. 반응 종료 후 추출한 후 컬럼정제하여 <중간체 18-1>을 8 g (수율 76.23%) 수득하였다.1-bromo-2,3,4,5,6-pentafluorobenzene (10 g, 0.040 mol, sigma aldrich), aniline (4.15 g, 0.044 mol, sigma aldrich), Sodium tert-butoxide (7.78 g, 0.081 mol, sigma 150 mL of Toluene was added to aldrich), catalyst Pd (dba) 2 (1.16 g, 0.002 mol, sigma aldrich), tri-tert-Bu-phosphine (0.82 g, 0.004 mol, sigma aldrich) and stirred at 100 ° C. for 5 hours. The reaction was carried out. After completion of the reaction, the mixture was extracted and purified by column to obtain 8 g (yield 76.23%) of <intermediate 18-1>.
(2) (2) 제조예Production Example 2 : 화합물 18의 합성 2: Synthesis of Compound 18
중간체 1-4 (10 g, 0.020 mol), 중간체 18-1 (11.63 g, 0.044 mol), Sodium tert-butoxide (7.84 g, 0.081 mol, sigma aldrich), 촉매 Pd(dba)2 (0.59 g, 0.001 mol, sigma aldrich), tri-tert-Bu-phosphine (0.41 g, 0.001 mol, sigma aldrich)에 Toluene 150 mL를 넣고 100 ℃에서 4시간 동안 교반하여 반응시켰다. 반응 종료 후 추출한 후 컬럼정제하여 화합물 18을 13 g (수율 75%) 수득하였다.Intermediate 1-4 (10 g, 0.020 mol), intermediate 18-1 (11.63 g, 0.044 mol), Sodium tert-butoxide (7.84 g, 0.081 mol, sigma aldrich), catalyst Pd (dba) 2 (0.59 g, 0.001 mol, sigma aldrich) and tri-tert-Bu-phosphine (0.41 g, 0.001 mol, sigma aldrich) were added 150 mL of Toluene and stirred at 100 ° C. for 4 hours. After completion of the reaction, the mixture was extracted and purified by column to obtain 13 g (yield 75%) of compound 18.
H-NMR (200MHz, CDCl3):δppm, 2H(8.79/s, 6.81/m) 4H(7.20/m, 6.29/d)H-NMR (200 MHz, CDCl 3): δ ppm, 2H (8.79 / s, 6.81 / m) 4H (7.20 / m, 6.29 / d)
LC/MS: m/z=846[(M+1)+]LC / MS: m / z = 846 [(M + l) + ]
합성예Synthesis Example 3 : 화합물 45 합성 3: Synthesis of Compound 45
(1) (One) 제조예Production Example 1 : 중간체 45-1의 합성 1: Synthesis of Intermediate 45-1
1-bromo-2,3,5,6-tetrafluoro-4-(trifluoromethyl)benzene (10 g, 0.033 mol, sigma aldrich), aniline (3.45 g, 0.037 mol, sigma aldrich), Sodium tert-butoxide (6.47 g, 0.067 mol, sigma aldrich), 촉매 Pd(dba)2 (0.97 g, 0.0017 mol, sigma aldrich), tri-tert-Bu-phosphine (0.68 g, 0.0034 mol, sigma aldrich)에 Toluene 150 mL를 넣고 100 ℃에서 5시간 동안 교반하여 반응시켰다. 반응 종료 후 추출한 후 컬럼정제하여 <중간체 45-1>을 8 g (수율 76.23%) 수득하였다.1-bromo-2,3,5,6-tetrafluoro-4- (trifluoromethyl) benzene (10 g, 0.033 mol, sigma aldrich), aniline (3.45 g, 0.037 mol, sigma aldrich), Sodium tert-butoxide (6.47 g 150 mL of Toluene was added to 0.067 mol, sigma aldrich, catalyst Pd (dba) 2 (0.97 g, 0.0017 mol, sigma aldrich) and tri-tert-Bu-phosphine (0.68 g, 0.0034 mol, sigma aldrich). The reaction was stirred for 5 hours at. After the completion of the reaction, the mixture was extracted and purified by column to obtain 8 g (yield 76.23%) of <intermediate 45-1>.
(2) (2) 제조예Production Example 2 : 중간체 45-2의 합성 2: Synthesis of Intermediate 45-2
중간체 45-1 (10 g, 0.032 mol), 4-bromophenylboronic acid (7.15 g, 0.035 mol, sigma aldrich), Sodium tert-butoxide (6.22 g, 0.064 mol, sigma aldrich), Pd(dba)2 (0.93 g, 0.0016 mol, sigma aldrich), tri-tert-Bu-phosphine (0.65 g, 0.0032 mol, sigma aldrich)에 Toluene 200 mL, EtOH 40 mL, H2O 20 mL 를 넣고 100 ℃에서 6시간 동안 교반하여 반응시켰다. 반응 종료 후 추출한 후 컬럼 정제하여 <중간체 45-2>를 10.8 g (수율 77.8%) 수득하였다.Intermediate 45-1 (10 g, 0.032 mol), 4-bromophenylboronic acid (7.15 g, 0.035 mol, sigma aldrich), Sodium tert-butoxide (6.22 g, 0.064 mol, sigma aldrich), Pd (dba) 2 (0.93 g Toluene 200 mL, EtOH 40 mL, H 2 O 20 mL was added to 0.0016 mol, sigma aldrich) and tri-tert-Bu-phosphine (0.65 g, 0.0032 mol, sigma aldrich). I was. After the completion of the reaction, the mixture was extracted and purified by column to obtain 10.8 g (yield 77.8%) of <intermediate 45-2>.
(3) (3) 제조예Production Example 3 : 화합물 45의 합성 3: Synthesis of Compound 45
중간체 1-4 (10 g, 0.020 mol), 중간체 45-2 (19.26 g, 0.044 mol), Sodium tert-butoxide (6.86 g, 0.071 mol, sigma aldrich), Pd(dba)2 (0.59 g, 0.001 mol, sigma aldrich), tri-tert-Bu-phosphine (0.41 g, 0.002 mol, sigma aldrich)에 Toluene 200 mL, EtOH 40 mL, H2O 20 mL를 넣고 100 ℃에서 6시간 동안 교반하여 반응시켰다. 반응 종료 후 추출한 후 컬럼 정제하여 화합물 45를 15.5 g (수율 69.1%) 수득하였다.Intermediate 1-4 (10 g, 0.020 mol), intermediate 45-2 (19.26 g, 0.044 mol), Sodium tert-butoxide (6.86 g, 0.071 mol, sigma aldrich), Pd (dba) 2 (0.59 g, 0.001 mol Toluene 200 mL, EtOH 40 mL, and H 2 O 20 mL were added to tri-tert-Bu-phosphine (0.41 g, 0.002 mol, sigma aldrich), and the mixture was stirred at 100 ° C. for 6 hours. After completion of the reaction, the mixture was extracted and purified by column to obtain 15.5 g (yield 69.1%) of compound 45.
H-NMR (200MHz, CDCl3):δppm, 2H(6.9/s, 6.81/m) 4H(7.20/m, 7.13/d, 6.63/d, 6.58/d)H-NMR (200 MHz, CDCl 3): δ ppm, 2H (6.9 / s, 6.81 / m) 4H (7.20 / m, 7.13 / d, 6.63 / d, 6.58 / d)
LC/MS: m/z=1098[(M+1)+]LC / MS: m / z = 1098 [(M + 1) + ]
합성예Synthesis Example 4 : 화합물 60 합성 4: Synthesis of Compound 60
(1) (One) 제조예Production Example 1 : 중간체 60-1의 합성 1: Synthesis of Intermediate 60-1
중간체 1-1 (10 g, 0.028 mol), 2,3,5,6-tetrafluoro-4-hydroxybenzaldehyde (12.34 g, 0.063 mol, Mascot), p-Toluenesulfonic acid (1.00 g, 0.0058 mol, sigma aldrich), DMF 250 mL 넣고 80 ℃에서 2시간 동안 교반하여 반응시켰다. 반응 종료 후 0.05 M 탄산나트륨 수용액을 이용하여 추출 한 후 컬럼정제 하여 <중간체 60-1>을 14 g (수율 69.7%) 수득하였다.Intermediate 1-1 (10 g, 0.028 mol), 2,3,5,6-tetrafluoro-4-hydroxybenzaldehyde (12.34 g, 0.063 mol, Mascot), p-Toluenesulfonic acid (1.00 g, 0.0058 mol, sigma aldrich), 250 mL of DMF was added and the reaction was stirred at 80 ° C. for 2 hours. After completion of the reaction, the mixture was extracted using 0.05 M aqueous sodium carbonate solution, and column purified to obtain 14 g (yield 69.7%) of <Intermediate 60-1>.
(2) (2) 제조예Production Example 2 : 중간체 60-2의 합성 2: Synthesis of Intermediate 60-2
중간체 60-1 (10 g, 0.014 mol), 과량의 MnO2, methylene chloride 150 mL를 넣고 환류 교반하여 24시간 동안 교반하여 반응시켰다. 반응 종료 후 추출한 후 컬럼정제하여 <중간체 60-2>를 8.3 g (수율 83.4%) 수득하였다.Intermediate 60-1 (10 g, 0.014 mol), excess MnO 2 and 150 mL of methylene chloride were added thereto, and the mixture was stirred under reflux for 24 hours to react. After completion of the reaction, the mixture was extracted and purified by column to obtain 8.3 g (yield 83.4%) of <intermediate 60-2>.
(3) (3) 제조예Production Example 3 : 중간체 60-3의 합성 3: Synthesis of Intermediate 60-3
중간체 60-2 (10 g, 0.014 mol), malononitrile (5.74 g, 0.086 mol, sigma aldrich), methylene chloride 300 mL 넣고 ice-bath상태에서 냉각시킨 후 TiCl4 (16.49 g, 0.086 mol, sigma aldrich)를 천천히 떨어드리고 pyridine (11.46 g, 0.144 mol)을 매우 천천히 적가한 후 1시간 후 ice bath 제거하고 24시간 동안 교반하여 반응시켰다. 반응 종료 후 염산 수용액으로 추출 후 컬럼정제하여 <중간체 60-3>을 8.5 g (수율 74.6%) 수득하였다.Intermediate 60-2 (10 g, 0.014 mol), malononitrile (5.74 g, 0.086 mol, sigma aldrich), 300 mL of methylene chloride, cooled in an ice-bath and cooled with TiCl 4 (16.49 g, 0.086 mol, sigma aldrich) was slowly dropped and pyridine (11.46 g, 0.144 mol) was added dropwise very slowly. After 1 hour, the ice bath was removed and stirred for 24 hours to react. After completion of the reaction, the mixture was extracted with an aqueous hydrochloric acid solution and then purified by column to obtain 8.5 g (yield 74.6%) of <intermediate 60-3>.
(4) (4) 제조예Production Example 4 : 화합물 60의 합성 4: Synthesis of Compound 60
중간체 60-3 (10 g, 0.012 mol), 4-(diphenylamino)phenylboronic acid (8.09 g, 0.028 mol, sigma aldrich), potassium carbonate (8.79 g, 0.063 mol, sigma aldrich), Pd(PPh3)4 (0.73 g, 0.0063 mol, sigma aldrich), Tol 200 mL, EtOH 40 mL, H2O 20 mL 넣고 12시간 동안 환류 교반하여 반응시켰다. 반응 종료 후 추출한 후 컬럼정제하여 화합물 60을 9.6 g (수율 67.6%) 수득하였다.Intermediate 60-3 (10 g, 0.012 mol), 4- (diphenylamino) phenylboronic acid (8.09 g, 0.028 mol, sigma aldrich), potassium carbonate (8.79 g, 0.063 mol, sigma aldrich), Pd (PPh 3 ) 4 ( 0.73 g, 0.0063 mol, sigma aldrich), Tol 200 mL, EtOH 40 mL, H 2 O 20 mL was added and reacted under reflux for 12 hours. After completion of the reaction, the mixture was extracted and purified by column to obtain 9.6 g (yield 67.6%) of compound 60.
H-NMR (200MHz, CDCl3):δppm, 2H(6.9/s) 4H(7.13/d, 6.81/m, 6.58/d) 8H(7.20/m, 6.63/d)H-NMR (200 MHz, CDCl 3): δ ppm, 2H (6.9 / s) 4H (7.13 / d, 6.81 / m, 6.58 / d) 8H (7.20 / m, 6.63 / d)
LC/MS: m/z=1115[(M+1)+]LC / MS: m / z = 1115 [(M + 1) + ]
소자 실시예Device Example
본 발명에 따른 실시예에서, ITO 투명 전극은 25 mm × 25 mm × 0.7 mm의 유리 기판 위에, ITO 투명 전극이 부착된 ITO 유리 기판을 이용하여, 발광 면적이 2 mm × 2 mm 크기가 되도록 패터닝한 후 세정하였다. 기판을 진공 챔버에 장착한 후 베이스 압력이 1 × 10-6 torr가 되도록 한 후 유기물을 상기 ITO위에 하기 구조로 유기물과 금속을 증착하였다.In an embodiment according to the present invention, the ITO transparent electrode is patterned on a glass substrate of 25 mm × 25 mm × 0.7 mm, using an ITO glass substrate with an ITO transparent electrode, so that the light emitting area is 2 mm × 2 mm in size. And then washed. The substrate was mounted in a vacuum chamber, and the base pressure was 1 × 10 −6 torr. Then, the organic material and the metal were deposited on the ITO with the following structure.
소자 실시예 1 내지 7Device Examples 1-7
본 발명에 따른 화합물을 정공수송 물질로 하여, 하기와 같은 소자 구조를 갖는 청색 발광 유기발광소자를 제조하여, 발광 효율을 포함한 발광 특성을 측정하였다.Using the compound according to the present invention as a hole transport material, a blue light emitting organic light emitting device having a device structure as described below was manufactured, and light emission characteristics including light emission efficiency were measured.
ITO / 정공수송층 (100 nm) / 전자저지층 (10 nm) / 발광층 (20 nm) / 전자수송층 (201:Liq 30 nm) / LiF (1 nm) / Al (100 nm)ITO / hole transport layer (100 nm) / electron blocking layer (10 nm) / light emitting layer (20 nm) / electron transport layer (201: Liq 30 nm) / LiF (1 nm) / Al (100 nm)
TO 투명 전극에 정공수송층을 본 발명에 따른 화학식 1, 18, 27, 32, 45, 60, 90을 사용하여 성막하였다. 정공저지층은 [EBL1]을 사용하여 10 nm의 두께로 성막하였다. 또한, 발광층에는 호스트 화합물로는 [BH1]을 사용하고, 도판트 화합물로 [BD1]을 사용하여 두께가 20 nm 정도가 되도록 성막하였으며, 추가로 전자 수송층(하기 [201] 화합물 Liq 50% 도핑) 30 nm 및 LiF 1 nm 및 알루미늄 100 nm를 증착법으로 성막하여 유기발광소자를 제조하였다.A hole transport layer was formed on the TO transparent electrode using Chemical Formulas 1, 18, 27, 32, 45, 60, and 90 according to the present invention. The hole blocking layer was formed to a thickness of 10 nm using [EBL1]. In the light emitting layer, [BH1] was used as the host compound, and [BD1] was used as the dopant compound, and the film was formed to have a thickness of about 20 nm. An organic light emitting diode was manufactured by depositing 30 nm, 1 nm of LiF, and 100 nm of aluminum by a deposition method.
소자 비교예 1Device Comparative Example 1
본 발명에 따른 상기 소자 실시예는 별도의 도핑을 하지 않고 본 발명에 따른 화합물을 정공수송층에 채용한 것을 특징으로 한다.The device embodiment according to the present invention is characterized in that the compound according to the present invention is employed in the hole transport layer without a separate doping.
이에 따라 소자 비교예 1을 위한 유기발광소자는 상기 실시예 1의 소자구조에서 정공수송층에 본 발명에 따른 화합물 화학식 1을 대신하여 α-NPB에 F4TCNQ를 5% 도핑한 화합물을 채용한 것으로 제외하고는 동일하게 제작하였다.Accordingly, the organic light emitting device for Comparative Example 1 is a device structure of Example 1, except that the compound in which the compound is doped with 5% F4TCNQ in α-NPB instead of the compound of Formula 1 according to the present invention in the hole transport layer Was produced in the same way.
실험예 1 : 소자 실시예 1 내지 7의 발광 특성Experimental Example 1 Luminescence Characteristics of Device Examples 1 to 7
상기 실시예에 따라 제조된 유기전계발광소자는 Source meter (Model 237, Keithley)와 휘도계 (PR-650, Photo Research)를 이용하여 전압, 전류 및 발광 효율을 측정하였고, 전류 밀도 10 mA/㎠가 되는 전압을 "구동 전압"으로 정의하여 비교하였다. 결과는 하기 [표 1]과 같다.In the organic light emitting diode manufactured according to the above embodiment, voltage, current, and luminous efficiency were measured using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research), and the current density was 10 mA / cm 2. The voltage to be defined as "drive voltage" was compared. The results are shown in the following [Table 1].
상기 [표 1]에 나타낸 결과를 살펴보면, 먼저, 본 발명에 따른 화합물을 소자 정공수송층에 적용한 경우에 종래 소자 (비교예 1)에 비하여 p-도핑물질을 사용하지 않았음에도 불구하고, 발광 효율, 양자 효율 등 발광 특성이 동등하거나 더 우수함을 확인할 수 있다.Looking at the results shown in [Table 1], first, when the compound according to the present invention is applied to the device hole transport layer, despite the p-doping material is not used compared to the conventional device (Comparative Example 1), luminous efficiency, It can be confirmed that luminescent properties such as quantum efficiency are equivalent or better.
[α-NPB] [EBL1] [BH1] [BD1] [201] [F4TCNQ][α-NPB] [EBL1] [BH1] [BD1] [201] [F4TCNQ]
Claims (8)
[화학식 Ⅰ]
[화학식 Ⅱ]
상기 [화학식 Ⅰ] 또는 [화학식 Ⅱ]에서,
R1 내지 R4는 각각 독립적으로 시아노기(CN), 니트로기(NO2), 할로겐기, 설포닐기(SO2R'), 설폭사이드기(SO3), 카르보닐기(COR') 또는 카르복실기(CO2R')이거나, 이들 중에서 선택되는 하나 이상이 치환된 탄소수 6 내지 30의 아릴기이거나 탄수소 2 내지 30의 헤테로아릴기이고,
상기 R'은 수소, 중수소, 시아노기, 할로겐기, 아미노기, 싸이올기, 히드록시기, 니트로기, 탄소수 1 내지 24의 알킬기, 탄소수 1 내지 24의 할로겐화된 알킬기, 탄소수 2 내지 24의 알케닐기, 탄소수 6 내지 24의 아릴기, 탄소수 2 내지 24의 헤테로아릴기, 탄소수 1 내기 24의 알콕시기, 탄소수 1 내지 24의 알킬실릴기 및 탄소수 1 내지 24의 아릴실릴기 중에서 선택되며,
R9 내지 R16은 각각 독립적으로 수소, 중수소 또는 할로겐기이고,
R5 내지 R8은 각각 수소, 시아노기, 할로겐기, 아미노기, 싸이올기, 히드록시기, 니트로기, 치환 또는 비치환된 탄소수 1 내지 24의 알킬기, 치환 또는 비치환된 탄소수 1 내지 24의 할로겐화된 알킬기, 치환 또는 비치환된 탄소수 2 내지 24의 알케닐기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 치환 또는 비치환된 탄소수 2 내지 30의 헤테로아릴기, 치환 또는 비치환된 탄소수 1 내기 24의 알콕시기, 치환 또는 비치환된 탄소수 1 내지 24의 알킬실릴기, 탄소수 6 내지 30의 아릴실릴기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴아민기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기 및 치환 또는 비치환된 탄소수 6 내지 30의 아릴싸이오기 중에서 선택되며,
상기 R5 내지 R6 중 적어도 어느 하나 및 R7 내지 R8 중 적어도 어느 하나는 하기 [구조식 1]과 [구조식 2] 중에서 선택되는 어느 하나이고,
[구조식 1]
[구조식 2]
상기 [구조식 1]과 [구조식 2]에서,
L1 및 L2는 각각 단일결합이거나, 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기 및 치환 또는 비치환된 탄소수 2 내지 30의 헤테로아릴렌기 중에서 선택되고, n 및 m은 각각 1 내지 4의 정수이며, n 및 m은 각각 2 이상인 경우, 복수 개의 L1 및 L2는 각각 서로 동일하거나 상이하고,
Ar1 내지 Ar3는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 5 내지 50의 아릴기 및 치환 또는 비치환된 탄소수 2 내지 50의 헤테로아릴기 중에서 선택되며,
상기 Ar1 및 Ar2는 서로 결합하거나 인접한 치환기와 연결되어 지환족, 방향족의 단일환 또는 다환 고리를 형성할 수 있으며, 상기 형성된 지환족, 방향족의 단일환 또는 다환 고리의 탄소원자는 N, S 및 O 중에서 선택되는 어느 하나 이상의 헤테로원자로 치환될 수 있고,
o, p 및 q는 각각 1 내지 3이 정수이고, 상기 o, p 및 q가 각각 2 이상인 경우 복수의 Ar1 내지 Ar3는 각각 서로 동일하거나 상이할 수 있으며,
상기 R5 내지 R6과, R7 내지 R8은 각각 서로 결합하거나 인접한 치환기와 연결되어 지환족, 방향족의 단일환 또는 다환 고리를 형성할 수 있으며, 상기 형성된 지환족, 방향족의 단일환 또는 다환 고리의 탄소원자는 N, S 및 O 중에서 선택되는 어느 하나 이상의 헤테로원자로 치환될 수 있다.An organic light emitting compound represented by the following [Formula I] or [Formula II]:
[Formula I]
[Formula II]
In [Formula I] or [Formula II],
R 1 to R 4 are each independently a cyano group (CN), a nitro group (NO 2 ), a halogen group, a sulfonyl group (SO 2 R '), a sulfoxide group (SO 3 ), a carbonyl group (COR'), or a carboxyl group ( CO 2 R '), or at least one selected from these is a substituted aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 30 carbon atoms,
R 'is hydrogen, deuterium, cyano group, halogen group, amino group, thiol group, hydroxy group, nitro group, alkyl group of 1 to 24 carbon atoms, halogenated alkyl group of 1 to 24 carbon atoms, alkenyl group of 2 to 24 carbon atoms, 6 carbon atoms It is selected from an aryl group of 24 to 24, a heteroaryl group of 2 to 24 carbon atoms, an alkoxy group of 1 to 24 carbon atoms, an alkylsilyl group of 1 to 24 carbon atoms and an arylsilyl group of 1 to 24 carbon atoms,
R 9 to R 16 are each independently hydrogen, deuterium or a halogen group,
R 5 to R 8 are each hydrogen, cyano group, halogen group, amino group, thiol group, hydroxy group, nitro group, substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, substituted or unsubstituted halogenated alkyl group having 1 to 24 carbon atoms, respectively. , Substituted or unsubstituted alkenyl group having 2 to 24 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon atoms 1 to 24 An alkoxy group, a substituted or unsubstituted C1-C24 alkylsilyl group, a C6-C30 arylsilyl group, a substituted or unsubstituted C6-C30 arylamine group, a substituted or unsubstituted C6-C30 Is selected from an aryloxy group and a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms,
At least one of the R 5 to R 6 and at least one of R 7 to R 8 is any one selected from the following [formula 1] and [formula 2],
[Formula 1]
[Formula 2]
In [Formula 1] and [Formula 2],
L 1 and L 2 are each a single bond or are selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, and n and m are each selected from 1 to 4 An integer, and when n and m are each 2 or more, a plurality of L 1 and L 2 are the same as or different from each other,
Ar 1 to Ar 3 are the same as or different from each other, each independently selected from a substituted or unsubstituted aryl group having 5 to 50 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms,
Ar 1 and Ar 2 may be bonded to each other or connected to an adjacent substituent to form an alicyclic or aromatic monocyclic or polycyclic ring, and the carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring may be N, S and May be substituted with any one or more heteroatoms selected from O,
o, p and q are each an integer of 1 to 3, when o, p and q are each 2 or more, a plurality of Ar 1 to Ar 3 may be the same or different from each other,
R 5 to R 6 and R 7 to R 8 may be bonded to each other or connected to an adjacent substituent to form an alicyclic or aromatic monocyclic or polycyclic ring, and the formed alicyclic or aromatic monocyclic or polycyclic ring The carbon atom of the ring may be substituted with any one or more heteroatoms selected from N, S and O.
하기 [화학식 Ⅰ] 또는 [화학식 Ⅱ]는 하기 [화학식 Ⅰ-1] 내지 [화학식 Ⅰ-2] 및 [화학식 Ⅱ-1] 내지 [화학식 Ⅱ-2] 중에서 선택되는 어느 하나인 것을 특징으로 하는 유기발광 화합물:
[화학식 Ⅰ-1] [화학식 Ⅰ-2]
[화학식 Ⅱ-1] [화학식 Ⅱ-2]
상기 [화학식 Ⅰ-1] 내지 [화학식 Ⅰ-2] 및 [화학식 Ⅱ-1] 내지 [화학식 Ⅱ-2]에서,
R1 내지 R4 및 R9 내지 R16은 각각 상기 [화학식 Ⅰ] 또는 [화학식 Ⅱ]에서의 정의와 동일하고,
R17 내지 R24는 각각 수소, 중수소, 시아노기, 할로겐기, 아미노기, 싸이올기, 히드록시기, 니트로기 및 탄소수 1 내지 24의 할로겐화된 알킬기 중에서 선택되는 어느 하나이고,
X는 O, S, -N-Ra 또는 -Ra-C-Rb- (상기 Ra 및 Rb는 각각 수소 또는 메틸기임)이다.The method of claim 1,
[Chemical Formula I] or [Chemical Formula II] may be any one selected from the following [Formula I-1] to [Formula I-2] and [Formula II-1] to [Formula II-2]. Luminescent Compounds:
[Formula I-1] [Formula I-2]
[Formula II-1] [Formula II-2]
In [Formula I-1] to [Formula I-2] and [Formula II-1] to [Formula II-2],
R 1 to R 4 and R 9 to R 16 are the same as defined in the above [Formula I] or [Formula II],
R 17 to R 24 are each selected from hydrogen, deuterium, cyano group, halogen group, amino group, thiol group, hydroxy group, nitro group and halogenated alkyl group having 1 to 24 carbon atoms,
X is O, S, -N-Ra or -Ra-C-Rb-, wherein Ra and Rb are each hydrogen or a methyl group.
상기 R5 내지 R8, L 및 Ar1 내지 Ar3은 각각 1종 이상의 치환기로 더 치환될 수 있고, 상기 1종 이상의 치환기는 중수소, 시아노기, 할로겐기, 아미노기, 싸이올기, 히드록시기, 니트로기, 탄소수 1 내지 24의 알킬기, 탄소수 1 내지 24의 할로겐화된 알킬기, 탄소수 2 내지 24의 알케닐기, 탄소수 6 내지 24의 아릴기, 탄소수 2 내지 24의 헤테로아릴기, 탄소수 1 내기 24의 알콕시기, 탄소수 1 내지 24의 탄소수 1 내지 24의 알킬실릴기 및 탄소수 1 내지 24의 아릴실릴기로 이루어진 군에서 선택되는 것을 특징으로 하는 유기발광 화합물.The method of claim 1,
R 5 to R 8 , L and Ar 1 to Ar 3 may each be further substituted with one or more substituents, and the one or more substituents may be deuterium, cyano group, halogen group, amino group, thiol group, hydroxy group, nitro group , An alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, An organic light emitting compound, characterized in that it is selected from the group consisting of an alkylsilyl group having 1 to 24 carbon atoms and an arylsilyl group having 1 to 24 carbon atoms.
상기 [화학식 Ⅰ] 또는 [화학식 Ⅱ]는 하기 [화합물 1] 내지 [화합물 106] 중에서 선택되는 것을 특징으로 하는 유기발광 화합물:
[Formula I] or [Formula II] is an organic light emitting compound, characterized in that selected from the following [Compound 1] to [Compound 106]:
상기 유기물층 중 1 층 이상은 제1항에 따른 [화학식 Ⅰ] 또는 [화학식 Ⅱ]의 유기발광 화합물을 포함하는 것인 유기발광소자.An organic light emitting device comprising a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode,
At least one layer of the organic material layer is an organic light emitting device comprising the organic light emitting compound of [I] or [II] according to claim 1.
상기 유기물층은 정공 주입층, 정공 수송층, 정공 주입과 정공 수송 기능을 동시에 하는 층, 전자 수송층, 전자 주입층, 전자 수송과 전자 주입 기능을 동시에 하는 층 및 발광층 중에서 선택되는 1층 이상을 포함하고,
상기 층들 중 1층 이상이 상기 [화학식 Ⅰ] 또는 [화학식 Ⅱ]로 표시되는 유기발광 화합물을 포함하는 것을 특징으로 하는 유기발광소자.The method of claim 5,
The organic material layer includes one or more layers selected from a hole injection layer, a hole transport layer, a layer simultaneously performing hole injection and hole transport functions, an electron transport layer, an electron injection layer, a layer simultaneously performing electron transport and electron injection functions, and a light emitting layer.
At least one of the layers is an organic light emitting device, characterized in that it comprises an organic light emitting compound represented by the above [Formula I] or [Formula II].
상기 정공 수송층 및 정공 주입과 정공 수송 기능을 동시에 하는 층 중에서 선택되는 어느 한 층에 상기 [화학식 Ⅰ] 또는 [화학식 Ⅱ]로 표시되는 유기발광 화합물을 포함하는 것을 특징으로 하는 유기발광소자.The method of claim 6,
An organic light emitting device comprising an organic light emitting compound represented by the above [Formula I] or [Formula II] in any one selected from the hole transporting layer and the layer simultaneously performing hole injection and hole transporting functions.
상기 정공 수송층, 또는 정공 주입과 정공 수송 기능을 동시에 하는 층은 각각 단일층으로 구성되는 것을 특징으로 하고, p-도펀트 도핑 공정없이 형성되며, 상기 [화학식 Ⅰ] 또는 [화학식 Ⅱ]로 표시되는 유기발광 화합물로 이루어진 것을 특징으로 하는 유기발광소자.The method of claim 7, wherein
The hole transporting layer, or the layer simultaneously performing hole injection and hole transporting functions, are each composed of a single layer, and are formed without a p-dopant doping process, and are represented by the above [Formula I] or [Formula II]. An organic light emitting device comprising a light emitting compound.
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