KR102675085B1 - 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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- KR102675085B1 KR102675085B1 KR1020180070934A KR20180070934A KR102675085B1 KR 102675085 B1 KR102675085 B1 KR 102675085B1 KR 1020180070934 A KR1020180070934 A KR 1020180070934A KR 20180070934 A KR20180070934 A KR 20180070934A KR 102675085 B1 KR102675085 B1 KR 102675085B1
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- 238000000034 method Methods 0.000 claims description 9
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
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.
[화학식 Ⅰ]
[화학식 Ⅱ]
The present invention implements low-voltage driving characteristics of the device without separate p-doping by introducing each moiety with p-doping function and hole transport characteristics into one structure and improves hole transport. It relates to an organic light-emitting compound represented by the following [Chemical Formula I] or [Chemical Formula II] that is excellent and can achieve improved luminous efficiency of the device.
[Formula Ⅰ]
[Formula Ⅱ]
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 organic light-emitting compounds, and more specifically, to organic light-emitting compounds used as hole transport materials for the hole injection layer or hole transport layer of organic light-emitting devices, and the use of the same to enable low-voltage driving and to have improved luminous efficiency and lifespan characteristics. This relates to significantly improved organic light emitting devices.
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, organic light emitting devices that are self-luminous and can be driven at low voltage have superior viewing angles and contrast ratios compared to liquid crystal displays, which are the mainstream flat display devices, do not require backlights, can be lightweight and thin, and are advantageous in terms of power consumption and color reproduction range. Due to its wide range, it is 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.Organic light-emitting devices are devices that emit light when electrons and holes are paired and then disappear when charges are injected into the organic light-emitting layer formed between the electron injection electrode (cathode) and the hole injection electrode (anode). It is a transparent material that can be bent like plastic. Not only can devices be formed on a substrate, but it has the advantage of being able to be driven at a low voltage of 10 V or less compared to a plasma display panel or inorganic light emitting display, consuming relatively little power, and providing excellent color. In addition, organic light emitting devices can display three colors, green, blue, and red, and are attracting much attention as next-generation rich color display devices.
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.Organic light-emitting devices use different organic layers to perform the processes required to emit light, that is, charge injection, charge transport, photoexciton formation, and light generation. Accordingly, organic light-emitting devices with a subdivided structure containing a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer between the anode and the cathode or more layers are being used, and the organic light-emitting devices have the above-mentioned characteristics. In order to achieve this, the materials that make up the organic layer within the device, such as hole injection material, hole transport material, light-emitting material, electron transport material, electron injection material, and electron blocking material, must first be supported by stable and efficient materials, but they are still stable. And the development of efficient organic material layer materials for organic light-emitting devices has not been sufficiently developed.
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 device and to achieve higher efficiency, longer life, and enlargement of the device, additional improvements are required in terms of efficiency and lifespan characteristics. In this regard, recently, hole holes in the structure of the organic light emitting device have been developed. Regarding the transport layer material, research is being conducted on doping p-type materials to improve the conductivity (mobility) of existing organic materials, or subdividing the layers to further provide a layer containing p-type material between the electrode and the hole transport layer. It is being 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, doping an organic material creates negative conductivity, which can lower the voltage drop in the transport layer even if it is a thick transport layer, and the thin space charge layer formed by increasing the doping level allows for effective charge injection by tunneling. By doping the hole transport layer, the high conductivity of the hole transport layer and the charge density of charge carriers can be controlled. Ultimately, the conductivity of the organic material layer is improved, improving the characteristics of the device, making it possible to implement a device with low driving voltage and high efficiency.
그러나, 추가적인 유기소재 및 유기층의 적용에 따른 공정 효율성이 떨어지고, 유기층의 두께 문제 등으로 저전압 구동의 구현이 어려워지는 등의 문제점이 여전히 존재한다.However, problems still exist, such as a decrease in process efficiency due to the application of additional organic materials and organic layers, and difficulty in implementing low-voltage driving due to problems with the thickness of the organic layer.
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.Therefore, the present invention aims to solve the above problems, by providing a compound with a fused material structure that can achieve both p-doping and hole transport without separately performing p-doping on the hole transport material, and introducing the compound. The aim is to provide an organic light-emitting device that can stably realize characteristics such as improved luminous efficiency and long lifespan, while also realizing low-voltage operation at a level equal to or higher than that of conventional devices.
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 an organic light emitting device in which each moiety, represented by the following [Chemical Formula I] or [Chemical Formula II] and having p-doping function and hole transport properties, is introduced into 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 [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 by combining a p-doping function and a hole transport characteristic, and devices incorporating this improve hole transport without additional p-doping compared to conventional devices. As a result, improved luminous efficiency and low-voltage driving at an equivalent level compared to conventional devices can be implemented, making it useful for various display devices. Compared to conventional devices, no process including a separate p-type layer or p-doping process is required. This can also improve device manufacturing process efficiency.
도 1은 본 발명에 따른 유기발광 화합물의 구조를 나타낸 대표도이다.1 is a representative diagram 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.The present invention implements low-voltage driving characteristics of the device without separate p-doping by introducing each moiety with p-doping function and hole transport characteristics into one structure and improves hole transport. It relates to an organic light-emitting compound represented by the following [Chemical Formula I] or [Chemical Formula II] that is excellent and can achieve improved luminous efficiency of the device.
[화학식 Ⅰ][Formula Ⅰ]
[화학식 Ⅱ][Formula Ⅱ]
상기 [화학식 Ⅰ] 또는 [화학식 Ⅱ]에서,In the [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 an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 30 carbon atoms in which one or more selected from among these is substituted, where R' is hydrogen, deuterium, cyano group, halogen group, Amino group, thiol group, hydroxy group, nitro group, alkyl group with 1 to 24 carbon atoms, halogenated alkyl group with 1 to 24 carbon atoms, alkenyl group with 2 to 24 carbon atoms, aryl group with 6 to 24 carbon atoms, heteroaryl group with 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 halogen.
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, a cyano group, a halogen group, an amino group, a thiol group, a hydroxy group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, or a substituted or unsubstituted halogenated alkyl group having 1 to 24 carbon atoms. , a substituted or unsubstituted alkenyl group having 2 to 24 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number of 1 to 24 an alkoxy group, a substituted or unsubstituted alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, or a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms. 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 one embodiment of the present invention, at least one of R 5 to R 6 and at least one of R 7 to R 8 may be any one selected from the following [Structural Formula 1] and [Structural Formula 2], , structures with these characteristics can be confirmed in specific compounds described later.
[구조식 1][Structural Formula 1]
[구조식 2][Structural Formula 2]
상기 [구조식 1]과 [구조식 2]에서,In [Structural Formula 1] and [Structural 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 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 1 to 4 carbon atoms. It is an integer, and 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 or different from each other, and are 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 adjacent substituents to form an alicyclic or aromatic monocyclic or polycyclic ring, and the carbon atom 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 integers from 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 each be bonded to each other or connected to adjacent substituents to form an alicyclic or aromatic monocyclic or polycyclic ring, and the formed alicyclic or aromatic monocyclic ring Alternatively, the carbon atom of the polycyclic ring may be substituted with any one or more heteroatoms selected from N, S, and O. According to one embodiment of the present invention, the following [Formula Ⅰ-1] to [Formula Ⅰ-2] and [Formula Ⅰ-1] It may be any one selected from [Formula 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 the [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 of the above [Formula Ⅰ] or [ The definition is the same as 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- (where Ra and Rb are hydrogen or methyl groups, respectively).
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 term 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, wherein the one or more substituents are deuterium , cyano group, halogen group, amino group, thiol group, hydroxy group, nitro group, alkyl group with 1 to 24 carbon atoms, halogenated alkyl group with 1 to 24 carbon atoms, alkenyl group with 2 to 24 carbon atoms, aryl group with 6 to 24 carbon atoms, carbon number It is selected from the group consisting of a heteroaryl group having 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.
본 발명에 있어서, 상기 치환기들의 예시들에 대해서 구체적으로 설명하면 아래와 같으나, 이에 한정되는 것은 아니다.In the present invention, examples of the above substituents will be described in detail as follows, but are 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 straight chain or branched, and specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, and 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, etc., but are not limited to these.
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. Examples of the monocyclic aryl group include phenyl group, biphenyl group, terphenyl group, and stilbene group, and examples of the polycyclic aryl group include naphthyl group and anthracenyl group. , phenanthrenyl group, pyrenyl group, perylenyl group, tetracenyl group, chrysenyl group, fluorenyl group, acenaphthacenyl group, triphenylene group, fluoranthrene group, etc., but the scope of the present invention is It is not limited 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 heteroatom, and examples of the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, and oxa group. Diazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, acridyl 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, benzooxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, dibenzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, etc. However, it 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 among the arylthio group, arylamine group, arylsilyl group, and aryloxy group is the same as the example of the aryl group described above.
본 발명에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.In the present invention, examples of halogen groups 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 or a polycyclic aryl group. The arylamine group containing two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group simultaneously.
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, and 2-methyl-biphenyl. Examples include, but are not limited to, an amine group, 9-methyl-anthracenylamine group, diphenyl amine group, phenyl naphthyl amine group, ditolyl amine group, phenyl tolyl amine group, carbazole group, and triphenyl amine group.
본 발명에 있어서, 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다.In the present invention, the silyl group specifically includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited to this.
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 as a substituent used in the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, and hexyloxy, and the alkoxy group One or more hydrogen atoms may be replaced 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), and bromine (Br).
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 alkenyl groups used in the present invention include linear or branched alkenyl groups, such as 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.
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 [Formula I] or [Formula II] can be used as an organic material layer of an organic light-emitting device due to its structural specificity, and more specifically, it can 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.In particular, conventionally, in order to control the high conductivity of the hole transport layer formed on the ITO substrate and the charge density of charge carriers, it is doped using a p-type dopant, or a layer made of a p-type dopant is added between the ITO substrate and the hole transport layer. was further inserted, but in the present invention, a single hole transport layer made of the compound represented by [Formula I] or [Formula II] can 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 to these.
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.In this way, the organic light-emitting compound according to the present invention is an organic light-emitting compound having unique properties of each introduced substituent by introducing each moiety having a p-doping function and hole transport characteristics into one structure. can be synthesized, and as a result, when the organic light-emitting compound according to the present invention is applied as a hole transport layer material, the low-voltage driving characteristics, luminous efficiency, and lifespan characteristics of the device can be further improved.
또한, 본 발명의 화합물은 일반적인 유기발광소자 제조방법에 따라 소자에 적용할 수 있다.Additionally, the compounds of the present invention can be applied to devices according to general organic light-emitting device manufacturing methods.
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 have a structure including a first electrode, a second electrode, and an organic material layer disposed between them, and the organic light-emitting compound according to the present invention is used in the organic material layer of the device. Except for this, it can be manufactured using conventional device manufacturing methods and materials.
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, or 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, etc. However, it is not limited to this and may include fewer or more 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.Therefore, in the organic light emitting device according to the present invention, the organic material layer may include one or more layers of a hole transport layer or a layer that simultaneously performs hole injection and hole transport, and one or more of the layers may be the [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 structure of the organic material layer of the preferred organic light emitting device according to the present invention will be described in more detail in the Examples described later.
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 deposits a metal, a conductive metal oxide, or an alloy thereof on a substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation. It can be manufactured by depositing an anode, forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and 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 this method, an organic light-emitting device can also be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate. The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, but is not limited to this and may have a single-layer structure. In addition, the organic material layer uses a variety of polymer materials to form a smaller number of layers by a solvent process, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, rather than deposition. It can be manufactured 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.The anode material is generally preferably a material with a large work function to facilitate hole injection into the organic layer. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), and 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 to these.
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.The cathode material is generally preferably a material with a small work function to facilitate electron injection into the organic layer. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof, multilayers such as LiF/Al or LiO 2 /Al. Structural materials, etc., but are not limited to these.
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 that can easily inject holes from the anode at a low voltage. It is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is 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 organic materials, hexanitrile hexaazatriphenylene, quinacridone-based organic materials, perylene-based organic materials, Examples include anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited to these.
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.The hole transport material is a material that can transport holes from the anode or hole injection layer and transfer them to the light emitting layer, and a material with high mobility for holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions. However, the low-voltage driving characteristics, luminous efficiency, and lifespan characteristics of the device can be improved by 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 that can emit light in the visible range by receiving holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining them, and a material with good quantum efficiency for fluorescence or phosphorescence is preferred. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ), carbazole-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole, benzthiazole, and Examples include benzimidazole-based compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene, and rubrene, but are not limited to these.
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.The electron transport material is a material that can easily inject electrons from the cathode and transfer them to the light-emitting layer, and a material with high mobility for electrons is suitable. Specific examples include, but are not limited to, an Al complex of 8-hydroxyquinoline, a complex containing Alq 3 , an organic radical compound, and a hydroxyflavone-metal complex.
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 front emitting type, a back emitting type, or a double-sided emitting type depending on 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 can function in organic electronic devices, including organic solar cells, organic photoreceptors, and organic transistors, on a principle similar to that applied to organic light-emitting devices.
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 embodiments. However, these examples are for illustrating 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 technical idea of the present invention as is known in the art. It will be self-evident to those with knowledge.
합성예Synthesis example 1 : 화합물 1 합성 1: Synthesis of Compound 1
(1) (One) 제조예Manufacturing 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.200 mL of 1,2,5,6-Tetraaminonaphthalene (10 g, 0.053 mol, Mascot.), N-Bromosuccinimide (19.86 g, 0.111 mol, Sigma aldrich), and Dimethylformamide were added and stirred at 60°C for 12 hours to react. After completion of the reaction, 1 M NaOH aqueous solution was added, stirred, filtered, and dried to obtain 15 g of <Intermediate 1-1> (yield 81.6%).
(2) (2) 제조예Manufacturing 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 stirred at room temperature for 24 hours to react. After completion of the reaction, extraction was performed and recrystallization was performed to obtain 9 g of <Intermediate 1-2> (yield 78.2%).
(3) (3) 제조예Manufacturing 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), an excess of MnO 2 , and 150 mL of methylene chloride were added, refluxed, and stirred for 24 hours to react. After completion of the reaction, extraction was performed and column purification was performed to obtain 8.3 g of <Intermediate 1-3> (yield 83.8%).
(4) (4) 제조예Manufacturing example 4 : 중간체 1-4의 합성 4: Synthesis of intermediates 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.Add Intermediate 1-3 (10 g, 0.025 mol), malononitrile (5.03 g, 0.076 mol, Sigma Aldrich), and 300 mL of methylene chloride, cool in an ice-bath, and add 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 stirred for 24 hours to react. After completion of the reaction, extraction was performed with an aqueous hydrochloric acid solution and column purification to obtain 9.8 g of <Intermediate 1-4> (yield 78.7%).
(5) (5) 제조예Manufacturing 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, 0.001 150 mL of toluene was added to tri-tert-Bu-phosphine (0.41 g, 0.002 mol, sigma aldrich) and stirred at 100°C for 5 hours to react. After completion of the reaction, extraction was performed and column purification was performed to obtain 10.5 g of Compound 1 (yield 77.1%).
H-NMR (200MHz, CDCl3):δppm, 2H(8.79/s) 4H(6.81/m) 8H(7.20/m, 6.29/d)H-NMR (200MHz, CDCl3):δppm, 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) 제조예Manufacturing 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 aldrich), catalyst Pd(dba) 2 (1.16 g, 0.002 mol, sigma aldrich), and tri-tert-Bu-phosphine (0.82 g, 0.004 mol, sigma aldrich) and stirred at 100°C for 5 hours. and reacted. After completion of the reaction, extraction was performed and column purification was performed to obtain 8 g of <Intermediate 18-1> (yield 76.23%).
(2) (2) 제조예Manufacturing 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, 0.001 150 mL of toluene was added to tri-tert-Bu-phosphine (0.41 g, 0.001 mol, sigma aldrich) and stirred at 100°C for 4 hours to react. After completion of the reaction, extraction was performed and column purification was performed to obtain 13 g of Compound 18 (yield 75%).
H-NMR (200MHz, CDCl3):δppm, 2H(8.79/s, 6.81/m) 4H(7.20/m, 6.29/d)H-NMR (200MHz, CDCl3):δppm, 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+1) + ]
합성예Synthesis example 3 : 화합물 45 합성 3: Synthesis of compound 45
(1) (One) 제조예Manufacturing 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 , 0.067 mol, sigma aldrich), catalyst Pd(dba) 2 (0.97 g, 0.0017 mol, sigma aldrich), tri-tert-Bu-phosphine (0.68 g, 0.0034 mol, sigma aldrich), add 150 mL of toluene and heat at 100°C. The reaction was stirred for 5 hours. After completion of the reaction, extraction was performed and column purification was performed to obtain 8 g of <Intermediate 45-1> (yield 76.23%).
(2) (2) 제조예Manufacturing 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) , 0.0016 mol, sigma aldrich), tri-tert-Bu-phosphine (0.65 g, 0.0032 mol, sigma aldrich), add 200 mL of Toluene, 40 mL of EtOH, and 20 mL of H 2 O and stir at 100°C for 6 hours to react. I ordered it. After completion of the reaction, extraction was performed and column purification was performed to obtain 10.8 g of <Intermediate 45-2> (yield 77.8%).
(3) (3) 제조예Manufacturing 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) , sigma aldrich), tri-tert-Bu-phosphine (0.41 g, 0.002 mol, sigma aldrich) were added with 200 mL of Toluene, 40 mL of EtOH, and 20 mL of H 2 O, and stirred at 100°C for 6 hours to react. After completion of the reaction, extraction was performed and column purification was performed to obtain 15.5 g of compound 45 (yield 69.1%).
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 (200MHz, CDCl3):δppm, 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) 제조예Manufacturing 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), Add 250 mL of DMF and stir at 80°C for 2 hours to react. After completion of the reaction, extraction was performed using a 0.05 M aqueous sodium carbonate solution, followed by column purification to obtain 14 g of <Intermediate 60-1> (yield 69.7%).
(2) (2) 제조예Manufacturing 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), an excess of MnO 2 , and 150 mL of methylene chloride were added, refluxed, and stirred for 24 hours to react. After completion of the reaction, extraction was performed and column purification was performed to obtain 8.3 g of <Intermediate 60-2> (yield 83.4%).
(3) (3) 제조예Manufacturing 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.Add Intermediate 60-2 (10 g, 0.014 mol), malononitrile (5.74 g, 0.086 mol, Sigma Aldrich), 300 mL of methylene chloride, cool in an ice-bath, and add 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, extraction was performed with an aqueous hydrochloric acid solution and column purification to obtain 8.5 g of <Intermediate 60-3> (yield 74.6%).
(4) (4) 제조예Manufacturing 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), 200 mL of Tol, 40 mL of EtOH, and 20 mL of H 2 O were added and stirred under reflux for 12 hours to react. After completion of the reaction, extraction was performed and column purification was performed to obtain 9.6 g of compound 60 (yield 67.6%).
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 (200MHz, CDCl3):δppm, 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 embodiment
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 so that the light emitting area is 2 mm × 2 mm using an ITO glass substrate to which the ITO transparent electrode is attached on a glass substrate of 25 mm × 25 mm × 0.7 mm. and then washed. After the substrate was mounted in a vacuum chamber and the base pressure was set to 1 × 10 -6 torr, organic materials and metals were deposited on the ITO in the following structure.
소자 실시예 1 내지 7Device Examples 1 to 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 the following device structure was manufactured, and the light-emitting properties, including light-emitting 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 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 addition, the light emitting layer was formed using [BH1] as a host compound and [BD1] as a dopant compound to a thickness of about 20 nm, and additionally an electron transport layer (50% doped with [201] compound Liq below). An organic light-emitting device was manufactured by depositing 30 nm of LiF, 1 nm of LiF, and 100 nm of aluminum by deposition.
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 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 Device Comparative Example 1 was except that in the device structure of Example 1, a compound in which α-NPB was doped with 5% F4TCNQ was adopted instead of the compound of formula 1 according to the present invention in the hole transport layer. was manufactured in the same way.
실험예 1 : 소자 실시예 1 내지 7의 발광 특성Experimental Example 1: Light emission 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.The voltage, current, and luminous efficiency of the organic electroluminescent device manufactured according to the above example were measured using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research), and the current density was 10 mA/cm2. The voltage was defined as “driving voltage” and compared. The results are shown in [Table 1] below.
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 hole transport layer of a device, the luminous efficiency, It can be confirmed that the luminescence properties, such as quantum efficiency, are equal or better.
[α-NPB] [EBL1] [BH1] [BD1] [201] [F4TCNQ][α-NPB] [EBL1] [BH1] [BD1] [201] [F4TCNQ]
Claims (9)
[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 6 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.Organic light-emitting compound represented by [Formula I] or [Formula II]:
[Formula Ⅰ]
[Formula Ⅱ]
In the [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 an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 30 carbon atoms, in which at least one selected from among these is substituted,
R' is hydrogen, deuterium, cyano group, halogen group, amino group, thiol group, hydroxy group, nitro group, alkyl group with 1 to 24 carbon atoms, halogenated alkyl group with 1 to 24 carbon atoms, alkenyl group with 2 to 24 carbon atoms, and 6 carbon atoms. It is selected from an aryl group with 2 to 24 carbon atoms, a heteroaryl group with 2 to 24 carbon atoms, an alkoxy group with 1 to 24 carbon atoms, an alkylsilyl group with 1 to 24 carbon atoms, and an arylsilyl group with 6 to 24 carbon atoms,
R 9 to R 16 are each independently hydrogen, deuterium, or halogen,
R 5 to R 8 are each hydrogen, a cyano group, a halogen group, an amino group, a thiol group, a hydroxy group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, or a substituted or unsubstituted halogenated alkyl group having 1 to 24 carbon atoms. , a substituted or unsubstituted alkenyl group having 2 to 24 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number of 1 to 24 an alkoxy group, a substituted or unsubstituted alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, or a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms. is selected from an aryloxy group and a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms,
At least one of R 5 to R 6 and at least one of R 7 to R 8 are selected from the following [Structural Formula 1] and [Structural Formula 2],
[Structural Formula 1]
[Structural Formula 2]
In [Structural Formula 1] and [Structural Formula 2],
L 1 and L 2 are each a single bond or 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 1 to 4 carbon atoms. is an integer, and when n and m are each 2 or more, a plurality of L 1 and L 2 are the same or different from each other,
Ar 1 to Ar 3 are the same or different from each other, and are 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 adjacent substituents to form an alicyclic, aromatic monocyclic or polycyclic ring, and the carbon atoms of the alicyclic, aromatic monocyclic or polycyclic ring formed are N, S and may be substituted with any one or more heteroatoms selected from O,
o, p and q are each integers from 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,
R 5 to R 6 and R 7 to R 8 may each be bonded to each other or connected to adjacent substituents to form an alicyclic, aromatic, monocyclic or polycyclic ring, and the formed alicyclic, 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.According to paragraph 1,
The following [Formula I] or [Formula II] is an organic compound selected from the following [Formula I-1] to [Formula I-2] and [Formula II-1] to [Formula II-2]. Luminescent Compound:
[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 each the same as defined in [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 hydrogen or methyl groups, respectively).
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 6 내지 24의 아릴실릴기로 이루어진 군에서 선택되는 것을 특징으로 하는 유기발광 화합물.According to paragraph 1,
Each of R 5 to R 8 , L and Ar 1 to Ar 3 may be further substituted with one or more substituents, and the one or more substituents include 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 selected from the group consisting of an alkylsilyl group having 1 to 24 carbon atoms and an arylsilyl group having 6 to 24 carbon atoms.
상기 [화학식 Ⅰ] 또는 [화학식 Ⅱ]는 하기 화합물 중에서 선택되는 어느 하나인 것을 특징으로 하는 유기발광 화합물:
According to paragraph 1,
[Formula I] or [Formula II] is an organic light-emitting compound, characterized in that any one selected from the following compounds:
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 one or more organic material layers disposed between the first electrode and the second electrode,
An organic light-emitting device wherein at least one layer of the organic material layer includes an organic light-emitting compound of [Formula I] or [Formula 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.According to clause 5,
The organic material layer includes one or more layers selected from a hole injection layer, a hole transport layer, a layer that performs both hole injection and hole transport functions, an electron transport layer, an electron injection layer, a layer that simultaneously performs electron transport and electron injection functions, and a light emitting layer,
An organic light-emitting device, wherein at least one of the layers includes an organic light-emitting compound represented by [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.According to clause 6,
An organic light-emitting device comprising an organic light-emitting compound represented by [Formula I] or [Formula II] in one layer selected from the hole transport layer and a layer that simultaneously performs hole injection and hole transport 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.In clause 7,
The hole transport layer, or the layer that performs both hole injection and hole transport functions, is characterized in that it is composed of a single layer, is formed without a p-dopant doping process, and is an organic compound represented by [Formula I] or [Formula II]. An organic light-emitting device characterized by consisting of a light-emitting compound.
Any one organic luminescent compound selected from the following compounds:
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