KR102050301B1 - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof Download PDF

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KR102050301B1
KR102050301B1 KR1020130053822A KR20130053822A KR102050301B1 KR 102050301 B1 KR102050301 B1 KR 102050301B1 KR 1020130053822 A KR1020130053822 A KR 1020130053822A KR 20130053822 A KR20130053822 A KR 20130053822A KR 102050301 B1 KR102050301 B1 KR 102050301B1
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KR20140134098A (en
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박남진
이선희
정화순
박보람
박정환
박성제
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덕산네오룩스 주식회사
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Abstract

본 발명은 소자의 발광효율, 안정성 및 수명을 향상시킬 수 있는 신규 화합물 및 이를 이용한 유기전기소자, 그 전자 장치를 제공한다.The present invention provides a novel compound that can improve the luminous efficiency, stability and life of the device, an organic electric device using the same, and an electronic device thereof.

Description

유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치{COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF}COMPONENT FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF

본 발명은 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치에 관한 것이다.The present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device thereof.

일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛 에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기전기소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물 층은 유기전기소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층 및 전자주입층 등으로 이루어질 수 있다. In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic electric element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. The organic layer is often made of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic electric device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.

유기전기소자에서 유기물층으로 사용되는 재료는 기능에 따라, 발광 재료와 전하수송 재료, 예컨대 정공주입 재료, 정공수송 재료, 전자수송 재료, 전자주입 재료 등으로 분류될 수 있다. The material used as the organic material layer in the organic electric element may be classified into a light emitting material and a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function.

한편, 유기전기소자의 수명단축 원인 중 하나인 양극전극(ITO)으로부터 금속 산화물이 유기층으로 침투 확산되는 것을 지연시키며, 소자 구동시 발생되는 주울열(Joule heating)에 대해서도 안정된 특성, 즉 높은 유리 전이 온도를 갖는 정공 주입층 재료에 대한 개발이 필요하다. 또한 정공 수송층 재료의 낮은 유리전이 온도는 소자 구동시에 박막 표면의 균일도가 무너지는 특성에 따라 소자수명에 큰 영향을 미치는 것으로 보고되고 있다. 또한, OLED 소자의 형성에 있어서 증착방법이 주류를 이루고 있으며, 이러한 증착방법에 오랫동안 견딜 수 있는 재료 즉 내열성 특성이 강한 재료가 필요한 실정이다. On the other hand, it delays the diffusion of metal oxide into the organic layer from the anode electrode (ITO), which is one of the causes of shortening the life of the organic electronic device, and stable characteristics, that is, high glass transition even for Joule heating generated when driving the device. There is a need for development of a hole injection layer material having a temperature. In addition, the low glass transition temperature of the hole transport layer material has been reported to have a significant effect on the device life, depending on the characteristics of the uniformity of the surface of the thin film when driving the device. In addition, the deposition method is the mainstream in the formation of the OLED device, a situation that requires a material that can withstand a long time, that is, a material having a strong heat resistance characteristics.

전술한 유기전기소자가 갖는 우수한 특징들을 충분히 발휘하기 위해서는 소자 내 유기물층을 이루는 물질, 예컨대 정공주입 물질, 정공수송 물질, 발광 물질, 전자수송 물질, 전자주입 물질 등이 안정하고 효율적인 재료에 의하여 뒷받침되는 것이 선행되어야 하나, 아직까지 안정하고 효율적인 유기전기소자용 유기물층 재료의 개발이 충분히 이루어지지 않은 상태이며, 따라서 새로운 재료의 개발이 계속 요구되고 있다.In order to fully exhibit the excellent characteristics of the above-described organic electroluminescent device, a material constituting the organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material. Although this should be preceded, the development of a stable and efficient organic material layer for an organic electric element has not yet been made sufficiently, and therefore, the development of new materials is continuously required.

본 발명은 소자의 높은 발광효율, 낮은 구동전압, 고내열성, 색순도 및 수명을 향상시킬 수 있는 화합물, 이를 이용한 유기전기소자 및 그 전자장치를 제공하는 것을 목적으로 한다. An object of the present invention is to provide a compound capable of improving high luminous efficiency, low driving voltage, high heat resistance, color purity, and lifetime of an element, an organic electric element using the same, and an electronic device thereof.

일 측면에서, 본 발명은 하기 화학식으로 표시되는 화합물을 제공한다.In one aspect, the present invention provides a compound represented by the following formula.

Figure 112013041999167-pat00001
Figure 112013041999167-pat00001

다른 측면에서, 본 발명은 상기 화학식으로 표시되는 화합물을 이용한 유기전기소자 및 그 전자장치를 제공한다.In another aspect, the present invention provides an organic electronic device using the compound represented by the above formula and an electronic device thereof.

본 발명에 따른 화합물을 이용함으로써 소자의 높은 발광효율, 낮은 구동전압, 고내열성을 달성할 수 있고, 소자의 색순도 및 수명을 크게 향상시킬 수 있다. By using the compound according to the present invention, high luminous efficiency, low driving voltage, and high heat resistance of the device can be achieved, and color purity and life of the device can be greatly improved.

도 1은 본 발명에 따른 유기전기발광소자의 예시도이다. 1 is an exemplary view of an organic electroluminescent device according to the present invention.

이하, 본 발명의 실시예를 첨부된 도면을 참조하여 상세하게 설명한다.Hereinafter, exemplary embodiments of the present invention will be described in detail with reference to the accompanying drawings.

각 도면의 구성요소들에 참조부호를 부가함에 있어서, 동일한 구성요소들에 대해서는 비록 다른 도면상에 표시되더라도 가능한 한 동일한 부호를 가지도록 하고 있음에 유의해야 한다. 또한, 본 발명을 설명함에 있어, 관련된 공지 구성 또는 기능에 대한 구체적인 설명이 본 발명의 요지를 흐릴 수 있다고 판단되는 경우에는 그 상세한 설명은 생략한다.In adding reference numerals to the components of each drawing, it should be noted that the same reference numerals are assigned to the same components as much as possible even though they are shown in different drawings. In addition, in describing the present invention, if it is determined that the detailed description of the related well-known configuration or function may obscure the gist of the present invention, the detailed description thereof will be omitted.

또한, 본 발명의 구성 요소를 설명하는 데 있어서, 제 1, 제 2, A, B, (a),(b) 등의 용어를 사용할 수 있다. 이러한 용어는 그 구성 요소를 다른 구성 요소와 구별하기 위한 것일 뿐, 그 용어에 의해 해당 구성 요소의 본질이나 차례 또는 순서 등이 한정되지 않는다. 어떤 구성 요소가 다른 구성요소에 "연결", "결합" 또는 "접속"된다고 기재된 경우, 그 구성 요소는 그 다른 구성요소에 직접적으로 연결되거나 또는 접속될 수 있지만, 각 구성 요소 사이에 또 다른 구성 요소가 "연결", "결합" 또는 "접속"될 수도 있다고 이해되어야 할 것이다.In addition, in describing the component of this invention, terms, such as 1st, 2nd, A, B, (a), (b), can be used. These terms are only for distinguishing the components from other components, and the nature, order or order of the components are not limited by the terms. If a component is described as being "connected", "coupled" or "connected" to another component, that component may be directly connected to or connected to that other component, but there may be another configuration between each component. It is to be understood that the elements may be "connected", "coupled" or "connected".

본 명세서 및 첨부된 청구의 범위에서 사용된 바와 같이, 달리 언급하지 않는 한, 하기 용어의 의미는 하기와 같다:As used in this specification and the appended claims, unless otherwise indicated, the meanings of the following terms are as follows:

본 명세서에서 사용된 용어 "할로" 또는 "할로겐"은 다른 설명이 없는 한 불소(F), 브롬(Br), 염소(Cl) 또는 요오드(I)이다.The term "halo" or "halogen" as used herein is fluorine (F), bromine (Br), chlorine (Cl) or iodine (I) unless otherwise indicated.

본 발명에 사용된 용어 "알킬" 또는 "알킬기"는 다른 설명이 없는 한 1 내지 60의 탄소수의 단일결합을 가지며, 직쇄 알킬기, 분지쇄 알킬기, 사이클로알킬(지환족)기, 알킬-치환된 사이클로알킬기, 사이클로알킬-치환된 알킬기를 비롯한 포화 지방족 작용기의 라디칼을 의미한다.As used herein, the term "alkyl" or "alkyl group" has a single bond of 1 to 60 carbon atoms, unless otherwise indicated, and is a straight chain alkyl group, branched chain alkyl group, cycloalkyl (alicyclic) group, alkyl-substituted cyclo Radicals of saturated aliphatic functional groups, including alkyl groups, cycloalkyl-substituted alkyl groups.

본 발명에 사용된 용어 "할로알킬기" 또는 "할로겐알킬기"는 다른 설명이 없는 한 할로겐으로 치환된 알킬기를 의미한다.As used herein, the term "haloalkyl group" or "halogenalkyl group" means an alkyl group substituted with halogen unless otherwise specified.

본 발명에 사용된 용어 "헤테로알킬기"는 알킬기를 구성하는 탄소 원자 중 하나 이상이 헤테로원자로 대체된 것을 의미한다.As used herein, the term "heteroalkyl group" means that at least one of the carbon atoms constituting the alkyl group has been replaced with a heteroatom.

본 발명에 사용된 용어 "알켄일기" 또는 "알킨일기"는 다른 설명이 없는 한 각각 2 내지 60의 탄소수의 이중결합 또는 삼중결합을 가지며, 직쇄형 또는 측쇄형 사슬기를 포함하며, 여기에 제한되는 것은 아니다. As used herein, the term "alkenyl group" or "alkynyl group", unless stated otherwise, has a double or triple bond of 2 to 60 carbon atoms, and includes a straight or branched chain group, and is not limited thereto. It is not.

본 발명에 사용된 용어 "시클로알킬"은 다른 설명이 없는 한 3 내지 60의 탄소수를 갖는 고리를 형성하는 알킬을 의미하며, 여기에 제한되는 것은 아니다. The term "cycloalkyl" as used herein, unless otherwise stated, refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto.

본 발명에 사용된 용어 "알콕실기", "알콕시기", 또는 "알킬옥시기"는 산소 라디칼이 부착된 알킬기를 의미하며, 다른 설명이 없는 한 1 내지 60의 탄소수를 가지며, 여기에 제한되는 것은 아니다. As used herein, the term "alkoxyl group", "alkoxy group", or "alkyloxy group" means an alkyl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 1 to 60, and is limited herein. It is not.

본 발명에 사용된 용어 "알켄옥실기", "알켄옥시기", "알켄일옥실기", 또는 "알켄일옥시기"는 산소 라디칼이 부착된 알켄일기를 의미하며, 다른 설명이 없는 한 2 내지 60의 탄소수를 가지며, 여기에 제한되는 것은 아니다. As used herein, the term "alkenoxyl group", "alkenoxy group", "alkenyloxyl group", or "alkenyloxy group" means an alkenyl group to which an oxygen radical is attached, and unless otherwise stated, 2 to 60 It has carbon number of, It is not limited to this.

본 발명에 사용된 용어 "아릴옥실기" 또는 "아릴옥시기"는 산소 라디칼이 부착된 아릴기를 의미하며, 다른 설명이 없는 한 6 내지 60의 탄소수를 가지며, 여기에 제한되는 것은 아니다. As used herein, the term "aryloxyl group" or "aryloxy group" means an aryl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 6 to 60, but is not limited thereto.

본 발명에 사용된 용어 "아릴기" 및 "아릴렌기"는 다른 설명이 없는 한 각각 6 내지 60의 탄소수를 가지며, 이에 제한되는 것은 아니다. 본 발명에서 아릴기 또는 아릴렌기는 단일 고리 또는 다중 고리의 방향족을 의미하며, 이웃한 치환기가 결합 또는 반응에 참여하여 형성된 방향족 고리를 포함한다. 예컨대, 아릴기는 페닐기, 비페닐기, 플루오렌기, 스파이로플루오렌기일 수 있다. As used herein, the terms "aryl group" and "arylene group" have a carbon number of 6 to 60 unless otherwise stated, but is not limited thereto. In the present invention, an aryl group or an arylene group means an aromatic of a single ring or multiple rings, and includes an aromatic ring formed by neighboring substituents participating in a bond or a reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, a spirofluorene group.

접두사 "아릴" 또는 "아르"는 아릴기로 치환된 라디칼을 의미한다. 예를 들어 아릴알킬기는 아릴기로 치환된 알킬기이며, 아릴알켄일기는 아릴기로 치환된 알켄일기이며, 아릴기로 치환된 라디칼은 본 명세서에서 설명한 탄소수를 가진다.The prefix "aryl" or "ar" means a radical substituted with an aryl group. For example, an arylalkyl group is an alkyl group substituted with an aryl group, an arylalkenyl group is an alkenyl group substituted with an aryl group, and the radical substituted with an aryl group has the carbon number described herein.

또한 접두사가 연속으로 명명되는 경우 먼저 기재된 순서대로 치환기가 나열되는 것을 의미한다. 예를 들어, 아릴알콕시기의 경우 아릴기로 치환된 알콕시기를 의미하며, 알콕실카르보닐기의 경우 알콕실기로 치환된 카르보닐기를 의미하며, 또한 아릴카르보닐알켄일기의 경우 아릴카르보닐기로 치환된 알켄일기를 의미하며 여기서 아릴카르보닐기는 아릴기로 치환된 카르보닐기이다.Also, when prefixes are named consecutively, it means that the substituents are listed in the order described first. For example, an arylalkoxy group means an alkoxy group substituted with an aryl group, an alkoxylcarbonyl group means a carbonyl group substituted with an alkoxyl group, and an arylcarbonylalkenyl group means an alkenyl group substituted with an arylcarbonyl group. Wherein the arylcarbonyl group is a carbonyl group substituted with an aryl group.

본 명세서에서 사용된 용어 "헤테로알킬"은 다른 설명이 없는 한 하나 이상의 헤테로원자를 포함하는 알킬을 의미한다. 본 발명에 사용된 용어 "헤테로아릴기" 또는 "헤테로아릴렌기"는 다른 설명이 없는 한 각각 하나 이상의 헤테로원자를 포함하는 탄소수 2 내지 60의 아릴기 또는 아릴렌기를 의미하며, 여기에 제한되는 것은 아니며, 단일 고리 및 다중 고리 중 적어도 하나를 포함하며, 이웃한 작용기기가 결합하여 형성될 수도 있다.As used herein, the term “heteroalkyl” means an alkyl including one or more heteroatoms unless otherwise indicated. As used herein, the term "heteroaryl group" or "heteroarylene group" means an aryl group or arylene group having 2 to 60 carbon atoms, each containing one or more heteroatoms, unless otherwise specified. It may include at least one of a single ring and multiple rings, and may be formed by combining adjacent functional groups.

본 발명에 사용된 용어 "헤테로고리기"는 다른 설명이 없는 한 하나 이상의 헤테로원자를 포함하고, 2 내지 60의 탄소수를 가지며, 단일 고리 및 다중 고리 중 적어도 하나를 포함하며, 헤테로지방족 고리 및 헤테로방향족 고리를 포함한다. 이웃한 작용기가 결합하여 형성될 수도 있다. As used herein, the term “heterocyclic group” includes one or more heteroatoms, unless otherwise indicated, and has from 2 to 60 carbon atoms, and includes at least one of a single ring and multiple rings, heteroaliphatic rings and hetero Aromatic rings. Adjacent functional groups may be formed in combination.

본 명세서에서 사용된 용어 "헤테로원자"는 다른 설명이 없는 한 N, O, S, P 또는 Si를 나타낸다. The term "heteroatom" as used herein refers to N, O, S, P or Si unless otherwise stated.

다른 설명이 없는 한, 본 발명에 사용된 용어 "지방족"은 탄소수 1 내지 60의 지방족 탄화수소를 의미하며, "지방족고리"는 탄소수 3 내지 60의 지방족 탄화수소 고리를 의미한다. Unless otherwise stated, the term "aliphatic" as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms, and the "aliphatic ring" means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

다른 설명이 없는 한, 본 발명에 사용된 용어 "포화 또는 불포화 고리"는 포화 또는 불포화 지방족고리 또는 탄소수 6 내지 60의 방향족고리 또는 헤테로고리를 의미한다.Unless otherwise stated, the term "saturated or unsaturated ring" as used herein means a saturated or unsaturated aliphatic ring or an aromatic ring or heterocyclic ring having 6 to 60 carbon atoms.

전술한 헤테로화합물 이외의 그 밖의 다른 헤테로화합물 또는 헤테로라디칼은 하나 이상의 헤테로원자를 포함하며, 여기에 제한되는 것은 아니다. Other heterocompounds or heteroradicals other than the aforementioned heterocompounds include, but are not limited to, one or more heteroatoms.

다른 설명이 없는 한, 본 발명에 사용된 용어 "카르보닐"이란 -COR'로 표시되는 것이며, 여기서 R'은 수소, 탄소수 1 내지 20 의 알킬기, 탄소수 6 내지 30 의 아릴기, 탄소수 3 내지 30의 사이클로알킬기, 탄소수 2 내지 20의 알켄일기, 탄소수 2 내지 20의 알킨일기, 또는 이들의 조합인 것이다.Unless otherwise stated, the term "carbonyl" used in the present invention is represented by -COR ', wherein R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and 3 to 30 carbon atoms. Cycloalkyl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.

다른 설명이 없는 한, 본 발명에 사용된 용어 "에테르"란 -R-O-R'로 표시되는 것이며, 여기서 R 또는 R'은 각각 서로 독립적으로 수소, 탄소수 1 내지 20의 알킬기, 탄소수 6 내지 30의 아릴기, 탄소수 3 내지 30의 사이클로알킬기, 탄소수 2 내지 20의 알켄일기, 탄소수 2 내지 20의 알킨일기, 또는 이들의 조합인 것인 것이다.Unless otherwise specified, the term "ether" as used herein is represented by -RO-R ', wherein R or R' are each independently of each other hydrogen, an alkyl group having 1 to 20 carbon atoms, It is an aryl group, a C3-C30 cycloalkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, or a combination thereof.

또한 명시적인 설명이 없는 한, 본 발명에서 사용된 용어 "치환 또는 비치환된"에서 "치환"은 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1~C20의 알킬기, C1~C20의 알콕실기, C1~C20의 알킬아민기, C1~C20의 알킬티오펜기, C6~C20의 아릴티오펜기, C2~C20의 알켄일기, C2~C20의 알킨일기, C3~C20의 시클로알킬기, C6~C20의 아릴기, 중수소로 치환된 C6~C20의 아릴기, C8~C20의 아릴알켄일기, 실란기, 붕소기, 게르마늄기, 및 C2~C20의 헤테로고리기로 이루어진 군으로부터 선택되는 1개 이상의 치환기로 치환됨을 의미하며, 이들 치환기에 제한되는 것은 아니다. Also, unless stated otherwise, the term "substituted" in the term "substituted or unsubstituted" as used in the present invention is deuterium, halogen, amino group, nitrile group, nitro group, C 1 ~ C 20 alkyl group, C 1 ~ C 20 alkoxyl group, C 1 ~ C 20 alkylamine group, C 1 ~ C 20 alkylthiophene group, C 6 ~ C 20 arylthiophene group, C 2 ~ C 20 alkenyl group, C 2 ~ C 20 alkynyl, C 3 ~ C 20 cycloalkyl group, C 6 ~ C 20 aryl group, of a C 6 ~ C 20 substituted by deuterium aryl group, a C 8 ~ C 20 aryl alkenyl group, a silane group, a boron Group, germanium group, and C 2 ~ C 20 It is meant to be substituted with one or more substituents selected from the group consisting of, but not limited to these substituents.

또한 명시적인 설명이 없는 한, 본 발명에서 사용되는 하기 화학식에서Also, unless expressly stated, in the formula

Figure 112013041999167-pat00002
Figure 112013041999167-pat00002

a가 0의 정수인 경우 치환기 R1은 부존재하며, a가 1의 정수인 경우 하나의 치환기 R1은 벤젠 고리를 형성하는 탄소 중 어느 하나의 탄소에 결합하며, a가 2 또는 3의 정수인 경우 각각 다음과 같이 결합하며 이때 R1은 서로 동일하거나 다를 수 있으며, a가 4 내지 6의 정수인 경우 이와 유사한 방식으로 벤젠 고리의 탄소에 결합하며, 한편 벤젠 고리를 형성하는 탄소에 결합된 수소의 표시는 생략한다.Substituent R 1 is absent when a is an integer of 0; when a is an integer of 1, one substituent R 1 is bonded to any one of carbons forming a benzene ring, and when a is an integer of 2 or 3, respectively R 1 may be the same or different from each other, and when a is an integer of 4 to 6, is bonded to the carbon of the benzene ring in a similar manner, while the indication of hydrogen bonded to the carbon forming the benzene ring is omitted. do.

Figure 112013041999167-pat00003
Figure 112013041999167-pat00003

(a=2) (a=3)                                (a = 2) (a = 3)

도 1은 본 발명에 일 실시예에 따른 유기전기소자에 대한 예시도이다.1 is an exemplary view of an organic electric device according to an embodiment of the present invention.

도 1을 참조하면, 본 발명에 따른 유기전기소자(100)는 기판(110) 상에 형성된 제 1전극(120), 제 2전극(180) 및 제 1전극(110)과 제 2전극(180) 사이에 본 발명에 따른 화합물을 포함하는 유기물층을 구비한다. 이때, 제 1전극(120)은 애노드(양극)이고, 제 2전극(180)은 캐소드(음극)일 수 있으며, 인버트형의 경우에는 제 1전극이 캐소드이고 제 2전극이 애노드일 수 있다.Referring to FIG. 1, the organic electric device 100 according to the present invention includes a first electrode 120, a second electrode 180, a first electrode 110, and a second electrode 180 formed on a substrate 110. ) Is provided with an organic material layer containing a compound according to the present invention. In this case, the first electrode 120 may be an anode (anode), the second electrode 180 may be a cathode (cathode), and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

유기물층은 제 1전극(120) 상에 순차적으로 정공주입층(130), 정공수송층(140), 발광층(150), 전자수송층(160) 및 전자주입층(170)을 포함할 수 있다. 이때, 발광층(150)을 제외한 나머지 층들이 형성되지 않을 수 있다. 정공저지층, 전자저지층, 발광보조층(151), 버퍼층(141) 등을 더 포함할 수도 있고, 전자수송층(160) 등이 정공저지층의 역할을 할 수도 있을 것이다. The organic layer may include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170 on the first electrode 120 in sequence. At this time, the remaining layers except for the light emitting layer 150 may not be formed. The hole blocking layer, the electron blocking layer, the light emitting auxiliary layer 151, the buffer layer 141 may be further included, and the electron transport layer 160 may serve as the hole blocking layer.

또한, 미도시하였지만, 본 발명에 따른 유기전기소자는 제 1전극과 제 2전극 중 적어도 일면 중 상기 유기물층과 반대되는 일면에 형성된 보호층 또는 광효율 개선층(Capping layer)을 더 포함할 수 있다. In addition, although not shown, the organic electric device according to the present invention may further include a protective layer or a light efficiency improving layer (Capping layer) formed on one surface of the at least one surface of the first electrode and the second electrode opposite to the organic material layer.

상기 유기물층에 적용되는 본 발명에 따른 화합물은 정공주입층(130), 정공수송층(140), 전자수송층(160), 전자주입층(170), 발광층(150)의 호스트 또는 도펀트 또는 캐핑층의 재료로 사용될 수 있을 것이다. 바람직하게는, 본 발명의 화합물은 발광층(150), 정공수송층(140) 및/또는 발광보조층(151)으로 사용될 수 있을 것이다.The compound according to the present invention applied to the organic material layer is a hole injection layer 130, a hole transport layer 140, an electron transport layer 160, the electron injection layer 170, the host of the light emitting layer 150 or the material of the dopant or capping layer Can be used as Preferably, the compound of the present invention may be used as the light emitting layer 150, hole transport layer 140 and / or light emitting auxiliary layer 151.

한편, 동일한 코어일지라도 어느 위치에 어느 치환기를 결합시키냐에 따라 밴드갭(band gap), 전기적 특성, 계면 특성 등이 달라질 수 있으므로, 코어의 선택 및 이에 결합된 서브(sub)-치환체의 조합도 아주 중요하며, 특히 각 유기물층 간의 에너지 준위 및 T1 값, 물질의 고유특성(mobility, 계면특성 등) 등이 최적의 조합을 이루었을 때 긴 수명과 높은 효율을 동시에 달성할 수 있다.Meanwhile, even in the same core, band gaps, electrical characteristics, and interface characteristics may vary depending on which substituents are bonded at which positions. Therefore, the selection of cores and the combination of sub-substituents bound thereto are also very significant. Importantly, long life and high efficiency can be achieved at the same time when an optimal combination of energy level and T1 value and intrinsic properties (mobility, interfacial properties, etc.) of each organic material layer is achieved.

이미 설명한 것과 같이, 최근 유기전기발광소자에 있어 정공수송층에서의 발광 문제를 해결하기 위해서는 정공수송층과 발광층 사이에 발광보조층이 형성하는 것이 바람직하며, 각각의 발광층(R, G, B)에 따른 서로 다른 발광보조층의 개발이 필요한 시점이다. 한편, 발광보조층의 경우 정공수송층 및 발광층(호스트)과의 상호관계를 파악해야하므로 모핵이 유사한 화합물을 사용하더라도 사용되는 유기물층이 달라지면 그 특징을 유추하기는 매우 어려울 것이다. As described above, in order to solve the light emission problem in the hole transport layer in the organic electroluminescent device, it is preferable to form a light emitting auxiliary layer between the hole transport layer and the light emitting layer, and according to each light emitting layer (R, G, B) It is time to develop different light emitting auxiliary layers. On the other hand, in the case of the light emitting auxiliary layer, it is very difficult to infer the characteristics if the organic material layer used is different even if a parent compound uses a compound similar to the hole transport layer and the light emitting layer (host).

따라서, 본 발명에서는 화학식 (1)로 표시되는 화합물을 사용하여 정공수송층, 발광층 또는 발광보조층을 형성함으로써 각 유기물층 간의 에너지 준위(level) 및 T1 값, 물질의 고유특성(이동도, 계면특성 등) 등을 최적화하여 유기전기소자의 수명 및 효율을 동시에 향상시킬 수 있다. Therefore, in the present invention, the hole transport layer, the light emitting layer, or the light emitting auxiliary layer is formed by using the compound represented by the formula (1), the energy level and T1 value between the organic material layers, the intrinsic properties (mobility, interface properties, etc.) ), Etc., can improve the life and efficiency of the organic electric device at the same time.

본 발명의 일 실시예에 따른 유기전기발광소자는 PVD(physical vapor deposition) 방법을 이용하여 제조될 수 있다. 예컨대, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극(120)을 형성하고, 그 위에 정공주입층(130), 정공수송층(140), 발광층(150), 전자수송층(160) 및 전자주입층(170)을 포함하는 유기물층을 형성한 후, 그 위에 음극(180)으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다.The organic electroluminescent device according to an embodiment of the present invention may be manufactured using a PVD method. For example, the anode 120 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, and the electron transport layer are formed thereon. After forming the organic material layer including the 160 and the electron injection layer 170, it can be prepared by depositing a material that can be used as the cathode 180 thereon.

또한, 유기물층은 다양한 고분자 소재를 사용하여 증착법이 아닌 용액 공정 또는 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. 본 발명에 따른 유기물층은 다양한 방법으로 형성될 수 있으므로, 그 형성방법에 의해 본 발명의 권리범위가 제한되는 것은 아니다.In addition, the organic material layer may be made by using a variety of polymer materials, and less by a solution process or a solvent process, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing or thermal transfer method, rather than deposition. It can be prepared in a number of layers. Since the organic material layer according to the present invention may be formed in various ways, the scope of the present invention is not limited by the forming method.

본 발명에 따른 유기전기소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic electric element according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.

WOLED(White Organic Light Emitting Device)는 고해상도 실현이 용이하고 공정성이 우수한 한편, 기존의LCD의 칼라필터 기술을 이용하여 제조될 수 있는 이점이 있다. 주로 백라이트 장치로 사용되는 백색 유기발광소자에 대한 다양한 구조들이 제안되고 특허화되고 있다. 대표적으로, R(Red), G(Green), B(Blue) 발광부들을 상호평면적으로 배치하는 병렬배치(side-by-side) 방식, 및 R, G, B 발광층이 상하로 적층되는 적층(stacking) 방식이 있고, 청색(B) 유기발광층에 의한 전계발광과 이로부터의 광을 이용하여 무기형광체의 자발광(photo-luminescence)을 이용하는 색변환물질(color conversion material, CCM) 방식 등이 있는데, 본 발명은 이러한 WOLED에도 적용될 수 있을 것이다.WOLED (White Organic Light Emitting Device) has the advantage that can be manufactured using the color filter technology of the existing LCD while being easy to realize high resolution and excellent processability. Various structures for white organic light emitting devices mainly used as backlight devices have been proposed and patented. Typically, a side-by-side method in which R (Red), G (Green), and B (Blue) light emitting parts are arranged in a plane, and a stack in which R, G, and B light emitting layers are stacked up and down ( stacking), and a color conversion material (CCM) method using electroluminescence by a blue (B) organic light emitting layer and photo-luminescence of inorganic phosphors using light therefrom. The present invention may also be applied to such WOLEDs.

또한, 본 발명에 따른 유기전기소자는 유기전기발광소자(OLED), 유기태양전지, 유기감광체(OPC), 유기트랜지스터(유기 TFT), 단색 또는 백색 조명용 소자 중 하나일 수 있다.In addition, the organic electroluminescent device according to the present invention may be one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), a monochromatic or white illumination device.

본 발명의 다른 실시예는 상술한 본 발명의 유기전기소자를 포함하는 디스플레이장치와, 이 디스플레이장치를 제어하는 제어부를 포함하는 전자장치를 포함할 수 있다. 이때, 전자장치는 현재 또는 장래의 유무선 통신단말일 수 있으며, 휴대폰 등의 이동 통신 단말기, PDA, 전자사전, PMP, 리모콘, 네비게이션, 게임기, 각종 TV, 각종 컴퓨터 등 모든 전자장치를 포함한다.
Another embodiment of the present invention may include a display device including the organic electric element of the present invention described above, and an electronic device including a control unit for controlling the display device. In this case, the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.

이하, 본 발명의 일 측면에 따른 화합물에 대하여 설명한다.Hereinafter, the compound which concerns on one aspect of this invention is demonstrated.

본 발명의 일 측면에 따른 화합물은 하기 화학식 1로 표시된다:Compounds according to one aspect of the present invention are represented by the following formula (1):

화학식 (1)Formula (1)

Figure 112013041999167-pat00004
Figure 112013041999167-pat00004

여기서,here,

X 및 Y는 각각 독립적으로 CRR, SiRR, NR', O 또는 S이며,X and Y are each independently CRR, SiRR, NR ', O or S,

R은 수소, C1~C50의 알킬기; C6~C60의 아릴기; O, N, S, Si, P 중 적어도 하나의 헤테로원자를 포함하는 C3~C60의 헤테로고리기;이거나, 또는 이웃하는 R의 경우 이들이 서로 결합하여 스파이로 화합물을 형성하며,R is hydrogen, an alkyl group of C 1 ~ C 50 ; C 6 ~ C 60 Aryl group; C 3 ~ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si, P; or, in the case of neighboring R, they combine with each other to form a spiro compound,

R'은 수소, C1~C50의 알킬기; C6~C60의 아릴기; O, N, S, Si, P 중 적어도 하나의 헤테로원자를 포함하는 C3~C60의 헤테로고리기;이며,R 'is hydrogen, an alkyl group of C 1 ~ C 50 ; C 6 ~ C 60 Aryl group; C 3 ~ C 60 Heterocyclic group containing at least one hetero atom of O, N, S, Si, P;

n=0 또는 1의 정수이며,is an integer of n = 0 or 1,

Ar1 내지 Ar4는 각각 서로 독립적으로 C6~C60의 아릴기; O, N, S, Si, P 중 적어도 하나의 헤테로원자를 포함하는 C3~C60의 헤테로고리기; C1~C50의 알킬기; 또는 플루오렌기;이며,Ar 1 to Ar 4 are each independently of the other C 6 ~ C 60 An aryl group; C 3 ~ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si, P; C 1 ~ C 50 Alkyl group; Or a fluorene group;

p, q, r, 및 s는 0 내지 3의 정수이며,p, q, r, and s are integers from 0 to 3,

R1 내지 R4는, 상기 p, q, r, 및 s가 2 이상인 경우 각각 복수로서 서로 동일하거나 상이하며, 서로 독립적으로 중수소; C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리와 C6~C60의 방향족고리의 융합고리기; C1~C50의 알킬기; C2~C20의 알켄일기; C2~C20의 알킨일기; C1~C30의 알콕실기; 및 C6~C30의 아릴옥시기로 이루어진 군에서 선택되거나, 또는 이들이 각각 서로 결합하여 고리를 형성하며,R 1 to R 4 are the same as or different from each other as a plurality when p, q, r, and s are 2 or more, and are each independently deuterium; C 6 ~ C 60 Aryl group; Fluorenyl groups; C 2 ~ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C 3 ~ C 60 of aliphatic rings and C 6 ~ C 60; C 1 ~ C 50 Alkyl group; C 2 ~ C 20 Alkenyl group; Alkynyl groups of C 2 to C 20 ; C 1 -C 30 alkoxyl group; And C 6 ~ C 30 It is selected from the group consisting of an aryloxy group, or they are combined with each other to form a ring,

R5 및 R6은 서로 독립적으로 수소; 중수소; C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리와 C6~C60의 방향족고리의 융합고리기; C1~C50의 알킬기; C2~C20의 알켄일기; C2~C20의 알킨일기; C1~C30의 알콕실기; 및 C6~C30의 아릴옥시기로 이루어진 군에서 선택되며,R 5 and R 6 are each independently hydrogen; heavy hydrogen; C 6 ~ C 60 Aryl group; Fluorenyl groups; C 2 ~ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C 3 ~ C 60 of aliphatic rings and C 6 ~ C 60; C 1 ~ C 50 Alkyl group; C 2 ~ C 20 Alkenyl group; Alkynyl groups of C 2 to C 20 ; C 1 -C 30 alkoxyl group; And it is selected from the group consisting of C 6 ~ C 30 aryloxy group,

상기 아릴기, 플루오렌일기, 헤테로고리기, 융합고리기, 알킬기, 알켄일기, 알킨일기, 알콕실기, 아릴옥시기는 중수소, 할로겐, 실란기, 실록산기, 붕소기, 게르마늄기, 시아노기, 니트로기, -L"-N(Rc)(Rd)(여기서 L", Rc 및 Rd는 각각 상기 L', Ra 및 Rb의 정의와 동일함), C1~C20의 알킬싸이오기, C1~C20의 알콕실기, C1~C20의 알킬기, C2~C20의 알켄일기, C2~C20의 알킨일기, C6~C20의 아릴기, 중수소로 치환된 C6~C20의 아릴기, 플루오렌일기, C2~C20의 헤테로고리기, C3~C20의 시클로알킬기, C7~C20의 아릴알킬기, 및 C8~C20의 아릴알켄일기로 이루어진 군에서 선택된 하나 이상의 치환기로 더욱 치환될 수 있다.The aryl group, fluorenyl group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxyl group, aryloxy group deuterium, halogen, silane group, siloxane group, boron group, germanium group, cyano group, nitro Group, -L "-N (R c ) (R d ), where L", R c and R d are the same as defined above for L ', R a and R b , alkyl of C 1 to C 20 Im coming, substituted alkynyl, aryl, heavy hydrogen of C 6 ~ C 20 of the C 1 ~ C 20 alkoxy group, C 1 ~ C 20 alkyl group, C 2 ~ C 20 alkenyl group, C 2 ~ C 20 of the C 6 ~ C 20 aryl group, fluorenyl group, C 2 ~ C 20 heterocyclic group, C 3 ~ C 20 cycloalkyl group, C 7 ~ C 20 arylalkyl group, and C 8 ~ C 20 aryl It may be further substituted with one or more substituents selected from the group consisting of alkenyl groups.

본 발명에 따르는 또 다른 실시예에서, 본 발명은 하기 화학식 (2) 또는 화학식 (3)으로 표시되는 화합물을 제공한다:In another embodiment according to the invention, the invention provides a compound represented by the following formula (2) or formula (3):

화학식 (2) 화학식 (3)         Formula (2) Formula (3)

Figure 112013041999167-pat00005
Figure 112013041999167-pat00006
.
Figure 112013041999167-pat00005
Figure 112013041999167-pat00006
.

본 발명에 따르는 또 다른 실시예에서, 본 발명은 하기 화학식 (1-1) 내지 화학식 (2-33) 중 어느 하나로 표시되는 화합물을 제공하며, 여기에 한정되는 것은 아니다:In another embodiment according to the invention, the invention provides, but is not limited to, a compound represented by any one of the following formulas (1-1) to (2-33):

Figure 112013041999167-pat00007
Figure 112013041999167-pat00007

Figure 112013041999167-pat00008
Figure 112013041999167-pat00008

Figure 112013041999167-pat00009
Figure 112013041999167-pat00009

본 발명에 따르는 또 다른 실시예에서, 본 발명은 제 1 전극, 제 2 전극, 및 상기 제 1 전극과 제 2 전극 사이에 위치하는 유기물층을 포함하며, 상기 유기물층은 본 발명의 일 실시예에 따르는 화합물을 함유하는 유기전기소자를 제공한다.In another embodiment according to the invention, the invention comprises a first electrode, a second electrode, and an organic layer located between the first and second electrodes, the organic layer according to an embodiment of the invention An organic electric device containing a compound is provided.

본 발명에 따르는 또 다른 실시예에서, 본 발명은 제 1 전극의 하부 또는 제 2 전극의 상부 중 적어도 하나에 광효율 개선층을 더욱 포함하는 유기전기소자를 제공한다.In another embodiment according to the present invention, the present invention provides an organic electroluminescent device further comprising a light efficiency improving layer on at least one of a lower portion of the first electrode or an upper portion of the second electrode.

본 발명에 따르는 또 다른 실시예에서, 본 발명은 본 발명의 일 실시예에 따르는 화합물을 용액공정(soluble process)에 의해 상기 유기물층으로 형성하는 것을 특징으로 하는 유기전기소자를 제공한다.In another embodiment according to the present invention, the present invention provides an organic electric device, characterized in that to form the compound according to an embodiment of the present invention to the organic material layer by a soluble process (soluble process).

본 발명에 따르는 또 다른 실시예에서, 본 발명은 발광층의 도펀트 물질로서 본 발명의 일 실시예에 따르는 화합물을 함유하는 것을 특징으로 하는 유기전기소자를 제공한다.In another embodiment according to the present invention, the present invention provides an organic electroluminescent device comprising a compound according to an embodiment of the present invention as a dopant material of a light emitting layer.

본 발명에 따르는 또 다른 실시예에서, 본 발명은 전술한 유기전기소자를 포함하는 디스플레이장치 및 상기 디스플레이장치를 구동하는 제어부를 포함하는 전자장치를 제공한다.In another embodiment according to the present invention, the present invention provides an electronic device including a display device including the above-described organic electroluminescent element and a control unit for driving the display device.

본 발명에 따르는 또 다른 실시예에서, 본 발명은 전술한 유기전기소자는 유기전기발광소자(OLED), 유기태양전지, 유기감광체(OPC), 유기트랜지스터(유기 TFT), 및 단색 또는 백색 조명용 소자 중 적어도 하나인 것을 특징으로 하는 전자장치를 제공한다.
In another embodiment according to the present invention, the organic electroluminescent device described above is an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a device for monochrome or white illumination It provides an electronic device characterized in that at least one of.

이하에서, 본 발명에 따른 화학식 (1)로 표시되는 화합물의 합성예 및 유기전기소자의 제조예에 관하여 실시예를 들어 구체적으로 설명하지만, 본 발명이 하기의 실시예로 한정되는 것은 아니다.
Hereinafter, the synthesis examples of the compound represented by the formula (1) and the production examples of the organic electric device according to the present invention will be described in detail with reference to Examples, but the present invention is not limited to the following Examples.

합성예Synthesis Example

상기 화합물의 합성은 하기와 같은 방법으로 수행하였다.Synthesis of the compound was carried out in the following manner.

최종 생성물(Final product ( finalfinal productsproducts ) 합성법 예시) Synthesis Example

본 발명에 따른 화합물(final products)은 하기 <반응식 1>로 반응하여 제조되나, 이에 한정된 것은 아니다.Compounds (final products) according to the present invention is prepared by reacting with <Reaction Scheme 1>, but is not limited thereto.

Figure 112013041999167-pat00010

Figure 112013041999167-pat00010

1. One. SubSub 1 화합물 1 compound

반응식 1의 sub 1 화합물은 하기 <반응식 2> 내지 <반응식 7>의 반응경로에 의해 합성될 수 있다.The sub 1 compound of Scheme 1 may be synthesized by the reaction pathways of <Scheme 2> to <Scheme 7>.

(1) (One) SubSub 1(A) 화합물 합성(X =  1 (A) Compound Synthesis (X = NRNR ')')

<반응식 2><Scheme 2>

Figure 112013041999167-pat00011
Figure 112013041999167-pat00011

SubSub 1-2 화합물 합성 1-2 Compound Synthesis

Sub 1-1 화합물(1 당량)을 둥근바닥플라스크에 DMF로 녹인 후에, Bis(pinacolato)diboron (2.2 당량), Pd(dppf)Cl2 (0.03 당량), KOAc(3 당량)를 첨가하고 90℃에서 교반하였다. 반응이 완료되면 증류를 통해 DMF를 제거하고 CH2Cl2와 물로 추출하였다. 유기층을 MgSO4로 건조하고 농축 한 후 생성된 화합물을 silicagel column 및 재결정하여 Sub 1-2 화합물을 얻었다.
Sub 1-1 compound (1 equiv) was dissolved in DMF in a round bottom flask, followed by addition of Bis (pinacolato) diboron (2.2 equiv), Pd (dppf) Cl 2 (0.03 equiv) and KOAc (3 equiv) at 90 ° C. Stirred at. After the reaction was completed, DMF was removed by distillation and extracted with CH 2 Cl 2 and water. The organic layer was dried over MgSO 4 , concentrated, and the resulting compound was purified by silicagel column and recrystallized to obtain a Sub 1-2 compound.

SubSub 1- One- 3 화합물 합성3 compound synthesis

얻은 Sub 1-2 화합물(1당량)과 1-bromo-4-iodobenzene (1당량), Pd(PPh3)4 (0.03당량), K2CO3(3당량)를 무수 THF와 소량의 물에 녹이고 난 후, 24시간 동안 환류시켰다. 반응이 종료되면 반응물의 온도를 상온으로 식히고, CH2Cl2로 추출하고 물로 닦아주었다. 소량의 물을 무수 MgSO4로 제거하고 감압 여과 후, 유기용매를 농축하여 생성된 생성물을 칼럼크로마토그래피를 이용하여 분리하여 원하는 Sub 1-3 화합물을 얻었다.
The obtained Sub 1-2 compound (1 equivalent), 1-bromo-4-iodobenzene (1 equivalent), Pd (PPh 3 ) 4 (0.03 equivalent), and K 2 CO 3 (3 equivalent) were dissolved in anhydrous THF and a small amount of water. After thawing, the mixture was refluxed for 24 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. A small amount of water was removed with anhydrous MgSO 4 , filtered under reduced pressure, and the organic solvent was concentrated, and the resulting product was separated by column chromatography to obtain a desired Sub 1-3 compound.

SubSub 1- One- 4 화합물 합성4 Compound Synthesis

얻은 Sub 1-3 화합물(1당량)과 4-bromo-1-iodo-2-nitrobenzene (1당량), Pd(PPh3)4 (0.03당량), K2CO3(3당량)를 무수 THF와 소량의 물에 녹이고 난 후, 24시간 동안 환류시켰다. 반응이 종료되면 반응물의 온도를 상온으로 식히고, CH2Cl2로 추출하고 물로 닦아주었다. 소량의 물을 무수 MgSO4로 제거하고 감압 여과 후, 유기용매를 농축하여 생성된 생성물을 칼럼크로마토그래피를 이용하여 분리하여 원하는 Sub 1-4 화합물을 얻었다.
The obtained Sub 1-3 compound (1 equiv), 4-bromo-1-iodo-2-nitrobenzene (1 equiv), Pd (PPh 3 ) 4 (0.03 equiv), and K 2 CO 3 (3 equiv) were combined with anhydrous THF After dissolving in a small amount of water, it was refluxed for 24 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. After removing a small amount of water with anhydrous MgSO 4 and filtered under reduced pressure, the organic solvent was concentrated and the resulting product was separated by column chromatography to give the desired Sub 1-4 compound.

SubSub 1-5 화합물 합성 1-5 Compound Synthesis

얻은 Sub 1-4 화합물(1당량)과 triphenylphosphine(2.5당량)을 o-dichlorobenzene에 녹이고, 24시간 동안 환류시켰다. 반응이 종결되면 감압 증류를 이용하여 용매를 제거한 후, 농축된 생성물을 칼럼크로마토그래피를 이용하여 분리하여 원하는 Sub 1-5 화합물을 얻었다.
The obtained Sub 1-4 compound (1 equivalent) and triphenylphosphine (2.5 equivalents) were dissolved in o-dichlorobenzene and refluxed for 24 hours. When the reaction was terminated, the solvent was removed by distillation under reduced pressure, and then the concentrated product was separated using column chromatography to obtain the desired Sub 1-5 compound.

SubSub 1(A) 화합물 합성 1 (A) Compound Synthesis

Sub 1-5 화합물(1당량)과 Sub 1-6 화합물(1.1당량)을 톨루엔에 넣고 Pd2(dba)3 (0.05당량), PPh3 (0.1당량), NaOt-Bu (3당량)을 각각 첨가한 뒤, 100℃ 에서 24시간 교반하면서 환류시켰다. ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축 한 후 생성된 유기물을 silicagel column 및 재결정하여 Sub 1(A) 화합물을 얻었다.
Sub 1-5 compound (1 equivalent) and Sub 1-6 compound (1.1 equivalent) were added to toluene. Pd 2 (dba) 3 (0.05 equivalent), PPh 3 (0.1 equiv) and NaO t -Bu (3 equiv) were added, respectively, and the mixture was refluxed at 100 ° C. for 24 hours with stirring. After extraction with ether and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to obtain Sub 1 (A) compound.

(2) (2) SubSub 1(B) 화합물 합성(X =  1 (B) Compound Synthesis (X = CRRCRR ))

<반응식 3><Scheme 3>

Figure 112013041999167-pat00012
Figure 112013041999167-pat00012

SubSub 1-7 1-7 화합물 합성 Compound synthesis

얻은 Sub 1-3 화합물(1당량)과 methyl 5-bromo-2-iodobenzoate (1당량), Pd(PPh3)4 (0.03당량), K2CO3(3당량)를 무수 THF와 소량의 물에 녹이고 난 후, 24시간 동안 환류시켰다. 반응이 종료되면 반응물의 온도를 상온으로 식히고, CH2Cl2로 추출하고 물로 닦아주었다. 소량의 물을 무수 MgSO4로 제거하고 감압 여과 후, 유기용매를 농축하여 생성된 생성물을 컬럼크로마토그래피를 이용하여 분리하여 원하는 Sub 1-7 화합물을 얻었다.
The obtained Sub 1-3 compound (1 equiv), methyl 5-bromo-2-iodobenzoate (1 equiv), Pd (PPh 3 ) 4 (0.03 equiv), K 2 CO 3 (3 equiv) were dissolved in anhydrous THF and a small amount of water After dissolving in, it was refluxed for 24 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. After removing a small amount of water with anhydrous MgSO 4 and filtered under reduced pressure, the organic solvent was concentrated and the resulting product was separated by column chromatography to give the desired Sub 1-7 compound.

SubSub 1- One- 9 화합물 합성9 Compound Synthesis

상기 합성에서 얻어진 Sub 1-7 화합물(1당량)을 THF에 녹인 후에, 반응물의 온도를 -75℃로 낮추고 Sub 1-8 화합물(2당량)을 넣었다. 4시간 동안 교반한 뒤 물을 넣어 희석시키고 2N HCl을 넣었다. 반응이 완료되면 ethyl acetate와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축 한 후 생성된 유기물을 silicagel column 및 재결정하여 Sub 1-9 화합물을 얻었다.
After dissolving the Sub 1-7 compound (1 equivalent) obtained in the above synthesis in THF, the temperature of the reactant was lowered to −75 ° C. and the Sub 1-8 compound (2 equivalents) was added thereto. After stirring for 4 hours, water was diluted, and 2N HCl was added thereto. After the reaction was completed, the mixture was extracted with ethyl acetate and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting organic material was purified by silicagel column and recrystallized to obtain Sub 1-9 compound.

SubSub 1(B) 화합물 합성1 (B) Compound Synthesis

상기 합성에서 얻어진 Sub 1-9 화합물(1당량)을 Acetic acid에 넣고, 반응물의 온도를 0℃로 낮추고 10분 동안 시켰다. 그 후 phosphoric acid를 추가시킨 후 20?에서 1시간 교반하였다. 마지막으로 Sudium hydroxide를 넣고 반응을 종료시켰다. 반응이 완료되면 ethyl acetate와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축 한 후 생성된 유기물을 silicagel column 및 재결정하여 Sub1(B)를 얻었다.
Sub 1-9 compound (1 equivalent) obtained in the above synthesis was added to Acetic acid, and the temperature of the reactant was lowered to 0 ° C. for 10 minutes. After adding phosphoric acid, the mixture was stirred at 20 ° for 1 hour. Finally, Sudium hydroxide was added to terminate the reaction. After the reaction was completed, the mixture was extracted with ethyl acetate and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to obtain Sub1 (B).

(3) (3) SubSub 1(C) 화합물 합성(X = S) 1 (C) Compound Synthesis (X = S)

<반응식 4><Scheme 4>

Figure 112013041999167-pat00013

Figure 112013041999167-pat00013

SubSub 1-10 화합물 합성 1-10 Compound Synthesis

Sub 1-3 화합물(1당량)과 4-bromo-1-iodo-2-(methylsulfinyl)benzene (1당량), Ph(PPh3), NaCO3를 무수 THF와 소량의 물에 녹이고 난 후, 24시간 동안 환류시켰다. 반응이 종료되면 반응물의 온도를 상온으로 식히고, CH2Cl2로 추출하고 물로 닦아주었다. 소량의 물을 무수 MgSO4로 제거하고 감압 여과 후, 유기용매를 농축하여 생성된 생성물을 컬럼크로마토그래피를 이용하여 분리하여 원하는 Sub 1-10 화합물을 얻었다.
Sub 1-3 dissolve compound (1 equiv), 4-bromo-1-iodo-2- (methylsulfinyl) benzene (1 equiv), Ph (PPh 3 ), NaCO 3 in dry THF and a small amount of water, It was refluxed for hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. After removing a small amount of water with anhydrous MgSO 4 and filtered under reduced pressure, the organic solvent was concentrated and the resulting product was separated by column chromatography to give the desired Sub 1-10 compound.

SubSub 1(C) 화합물 합성 1 (C) Compound Synthesis

Sub 1-10 화합물을 trifluoromethanesulfonic acid 용매에 녹인 후, 상온에서 48시간 동안 교반시켰다. 반응이 종료되면 반응물을 물과 pyridine 의 혼합용매에 붓고, 20분 동안 환류시켰다. 반응물의 온도를 상온으로 식히고, CH2Cl2 로 추출하고 닦아주었다. 소량의 물을 무수 MgSO4로 제거하고 감압 여과 후, 유기용매를 농축하여 생성된 생성물을 컬럼크로마토그래피를 이용하여 분리하여 원하는 Sub 1 (C) 화합물을 얻었다.
Sub 1-10 was dissolved in a trifluoromethanesulfonic acid solvent, and then stirred at room temperature for 48 hours. After the reaction was completed, the reaction was poured into a mixed solvent of water and pyridine and refluxed for 20 minutes. The temperature of the reaction was cooled to room temperature, extracted with CH 2 Cl 2 and wiped off. After removing a small amount of water with anhydrous MgSO 4 and filtered under reduced pressure, the organic solvent was concentrated and the resulting product was separated by column chromatography to give the desired Sub 1 (C) compound.

(4) (4) SubSub 1(D) 화합물 합성(Y,X =  1 (D) Compound Synthesis (Y, X = NRNR ')')

<반응식 5>Scheme 5

Figure 112013041999167-pat00014
Figure 112013041999167-pat00014

Figure 112013041999167-pat00015
Figure 112013041999167-pat00015

SubSub 1-11 화합물 합성 1-11 Compound Synthesis

얻은 Sub 1-2 화합물(1당량)과 1-bromo-4-iodobenzene (2.2당량), Pd(PPh3)4 (0.03당량), K2CO3(3당량)를 무수 THF와 소량의 물에 녹이고 난 후, 24시간 동안 환류시켰다. 반응이 종료되면 반응물의 온도를 상온으로 식히고, CH2Cl2로 추출하고 물로 닦아주었다. 소량의 물을 무수 MgSO4로 제거하고 감압 여과 후, 유기용매를 농축하여 생성된 생성물을 컬럼크로마토그래피를 이용하여 분리하여 원하는 Sub 1-11 화합물을 얻었다.
The obtained Sub 1-2 compound (1 equiv), 1-bromo-4-iodobenzene (2.2 equiv), Pd (PPh 3 ) 4 (0.03 equiv), and K 2 CO 3 (3 equiv) were dissolved in anhydrous THF and a small amount of water. After thawing, the mixture was refluxed for 24 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. A small amount of water was removed with anhydrous MgSO 4 , filtered under reduced pressure, and the organic solvent was concentrated and the resulting product was separated using column chromatography to obtain the desired Sub 1-11 compound.

SubSub 1-12 화합물합성 1-12 Compound Synthesis

얻은 Sub 1-11 화합물(1당량)과 triphenylphosphine(2.5당량)을 o-dichlorobenzene에 녹이고, 24시간 동안 환류시켰다. 반응이 종결되면 감압 증류를 이용하여 용매를 제거한 후, 농축된 생성물을 컬럼크로마토그래피를 이용하여 분리하여 원하는 Sub 1-12 화합물을 얻었다
The obtained Sub 1-11 compound (1 equivalent) and triphenylphosphine (2.5 equivalents) were dissolved in o-dichlorobenzene and refluxed for 24 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure, and the concentrated product was separated by column chromatography to obtain the desired Sub 1-12 compound.

SubSub 1(D) 화합물 합성법 1 (D) compound synthesis method

Sub 1-12 화합물(1당량)과 Sub 1-6 화합물(2.2당량)을 톨루엔에 넣고 Pd2(dba)3 (0.05당량), PPh3 (0.1당량), NaOt-Bu (3당량)을 각각 첨가한 뒤, 100℃ 에서 24시간 교반하면서 환류시켰다. ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축 한 후 생성된 유기물을 silicagel column 및 재결정하여 Sub 1(D) 화합물을 얻었다.
Sub 1-12 compound (1 equivalent) and Sub 1-6 compound (2.2 equivalent) were added to toluene. Pd 2 (dba) 3 (0.05 equivalent), PPh 3 (0.1 equiv) and NaO t -Bu (3 equiv) were added, respectively, and the mixture was refluxed at 100 ° C. for 24 hours with stirring. After extraction with ether and water, the organic layer was dried over MgSO 4 , concentrated, and the resulting organic material was purified by silicagel column and recrystallized to obtain Sub 1 (D) compound.

(5) (5) SubSub 1(E) 화합물 합성(Y,X =  1 (E) Compound Synthesis (Y, X = CRRCRR ))

<반응식 6><Scheme 6>

Figure 112013041999167-pat00016
Figure 112013041999167-pat00016

SubSub 1-13 화합물 합성 1-13 Compound Synthesis

얻은 Sub 1-2 화합물(1당량)과 methyl 5-bromo-2-iodobenzoate (2.2당량), Pd(PPh3)4 (0.03당량), K2CO3(3당량)를 무수 THF와 소량의 물에 녹이고 난 후, 24시간 동안 환류시켰다. 반응이 종료되면 반응물의 온도를 상온으로 식히고, CH2Cl2로 추출하고 물로 닦아주었다. 소량의 물을 무수 MgSO4로 제거하고 감압 여과 후, 유기용매를 농축하여 생성된 생성물을 컬럼크로마토그래피를 이용하여 분리하여 원하는 Sub 1-13 화합물을 얻었다
The obtained Sub 1-2 compound (1 equiv), methyl 5-bromo-2-iodobenzoate (2.2 equiv), Pd (PPh 3 ) 4 (0.03 equiv), K 2 CO 3 (3 equiv) were dissolved in anhydrous THF and a small amount of water After dissolving in, it was refluxed for 24 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. A small amount of water was removed with anhydrous MgSO 4 , filtered under reduced pressure, and the organic solvent was concentrated. The resulting product was separated using column chromatography to obtain the desired Sub 1-13 compound.

SubSub 1-14 화합물 합성 1-14 Compound Synthesis

상기 합성에서 얻어진 Sub 1-13 화합물(1당량)을 THF에 녹인 후에, 반응물의 온도를 -75℃로 낮추고 Sub 1-8 화합물(4당량)을 넣었다. 4시간 동안 교반한 뒤 물을 넣어 희석시키고 2N HCl을 넣었다. 반응이 완료되면 ethyl acetate와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축 한 후 생성된 유기물을 silicagel column 및 재결정하여 Sub 1-14 화합물을 얻었다.
After dissolving the Sub 1-13 compound (1 equivalent) obtained in the above synthesis in THF, the temperature of the reactant was lowered to −75 ° C. and the Sub 1-8 compound (4 equivalents) was added thereto. After stirring for 4 hours, water was diluted, and 2N HCl was added thereto. After the reaction was completed, the mixture was extracted with ethyl acetate and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting organic material was purified by silicagel column and recrystallized to obtain Sub 1-14 compound.

SubSub 1(E) 화합물 합성 1 (E) Compound Synthesis

상기 합성에서 얻어진 Sub 1-14 화합물(1당량)을 Acetic acid에 넣고, 반응물의 온도를 0℃로 낮추고 10분 동안 시켰다. 그 후 phosphoric acid를 추가시킨 후 20℃에서 1시간 교반한다. 마지막으로 Sudium hydroxide를 넣고 반응을 종료시켰다. 반응이 완료되면 ethyl acetate와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축 한 후 생성된 유기물을 silicagel column 및 재결정하여 Sub1(E) 화합물을 얻었다.
Sub 1-14 compound (1 equivalent) obtained in the above synthesis was added to Acetic acid, and the temperature of the reaction was lowered to 0 ° C. for 10 minutes. After adding phosphoric acid, it is stirred at 20 ° C for 1 hour. Finally, Sudium hydroxide was added to terminate the reaction. After the reaction was completed, the mixture was extracted with ethyl acetate and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting organic material was purified by silicagel column and recrystallized to obtain Sub1 (E) compound.

(6) (6) SubSub 1(F) 화합물 합성(Y,X = S) 1 (F) Compound Synthesis (Y, X = S)

<반응식 7>Scheme 7

Figure 112013041999167-pat00017
Figure 112013041999167-pat00017

SubSub 1-15 화합물 합성 1-15 Compound Synthesis

Sub 1-2 화합물(1당량)과 4-bromo-1-iodo-2-(methylsulfinyl)benzene (2.2당량), Ph(PPh3), NaCO3를 무수 THF와 소량의 물에 녹이고 난 후, 24시간 동안 환류시켰다. 반응이 종료되면 반응물의 온도를 상온으로 식히고, CH2Cl2로 추출하고 물로 닦아주었다. 소량의 물을 무수 MgSO4로 제거하고 감압 여과 후, 유기용매를 농축하여 생성된 생성물을 컬럼크로마토그래피를 이용하여 분리하여 원하는 Sub 1-15 화합물을 얻었다.
Sub 1-2 compound (1 equiv), 4-bromo-1-iodo-2- (methylsulfinyl) benzene (2.2 equiv), Ph (PPh 3 ), NaCO 3 dissolved in anhydrous THF and a small amount of water, It was refluxed for hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. After removing a small amount of water with anhydrous MgSO 4 and filtered under reduced pressure, the organic solvent was concentrated and the resulting product was separated by column chromatography to give the desired Sub 1-15 compound.

SubSub 1(F) 화합물 합성 1 (F) Compound Synthesis

Sub 1-15 화합물을 trifluoromethanesulfonic acid 용매에 녹인 후, 상온에서 48시간 동안 교반시켰다. 반응이 종료되면 반응물을 물과 pyridine 의 혼합용매에 붓고, 20분 동안 환류시켰다. 반응물의 온도를 상온으로 식히고, CH2Cl2 로 추출하고 닦아주었다. 소량의 물을 무수 MgSO4로 제거하고 감압 여과 후, 유기용매를 농축하여 생성된 생성물을 컬럼크로마토그래피를 이용하여 분리하여 원하는 Sub 1 (F) 화합물을 얻었다.
Sub 1-15 was dissolved in a trifluoromethanesulfonic acid solvent, and then stirred at room temperature for 48 hours. After the reaction was completed, the reaction was poured into a mixed solvent of water and pyridine and refluxed for 20 minutes. The temperature of the reaction was cooled to room temperature, extracted with CH 2 Cl 2 and wiped off. A small amount of water was removed with anhydrous MgSO 4 , filtered under reduced pressure, and the organic solvent was concentrated. The resulting product was separated using column chromatography to obtain the desired Sub 1 (F) compound.

Sub 1 화합물의 예는 다음 화합물을 포함하나, 여기에 한정되는 것은 아니다. Examples of Sub 1 compounds include, but are not limited to the following compounds.

Figure 112013041999167-pat00018
Figure 112013041999167-pat00018

Figure 112013041999167-pat00019

Figure 112013041999167-pat00019

상기 Sub 1 화합물의 합성 데이터를 아래 표 1에 나타낸다.Synthesis data of the Sub 1 compound is shown in Table 1 below.

Figure 112013041999167-pat00020
Figure 112013041999167-pat00020

2. 2. SubSub 2 화합물 2 compound

본 발명의 일 실시예에서 사용되는 Sub 2 화합물의 예에는 다음 화합물이 포함되나, 이에 한정되는 것은 아니다. Examples of Sub 2 compounds used in one embodiment of the present invention include, but are not limited to the following compounds.

Figure 112013041999167-pat00021
Figure 112013041999167-pat00021

Figure 112013041999167-pat00022
Figure 112013041999167-pat00022

Figure 112013041999167-pat00023
Figure 112013041999167-pat00023

Figure 112013041999167-pat00024
Figure 112013041999167-pat00024

Figure 112013041999167-pat00025
Figure 112013041999167-pat00025

Figure 112013041999167-pat00026
Figure 112013041999167-pat00026

Figure 112013041999167-pat00027

Figure 112013041999167-pat00027

상기 Sub 2 화합물의 예에 포함되는 화합물의 합성 데이터를 아래 표 2에 제시한다.Synthesis data of the compounds included in the examples of the Sub 2 compounds are shown in Table 2 below.

Figure 112013041999167-pat00028
Figure 112013041999167-pat00028

3. 최종 생성물3. Final product

이하에서 본 발명에 따르는 화합물의 합성법의 예를 제시하지만, 여기에 제한되는 것은 아니다.Examples of the synthesis method of the compound according to the present invention are shown below, but are not limited thereto.

Sub 1 화합물(1당량)과 Sub 2 화합물(2당량)을 톨루엔에 넣고 Pd2(dba)3 (0.05당량), PPh3 (0.1당량), NaOt-Bu (3당량)을 각각 첨가한 뒤, 100℃에서 24시간 교반 환류시켰다. ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축 한 후 생성된 유기물을 silicagel column 및 재결정하여 최종 생성물을 얻었다.
Sub 1 compound (1 equivalent) and Sub 2 compound (2 equivalents) were added to toluene. Pd 2 (dba) 3 (0.05 equivalents), PPh 3 (0.1 equiv) and NaO t -Bu (3 equiv) were added respectively, followed by stirring under reflux at 100 ° C. for 24 hours. After extraction with ether and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting organic material was purified by silicagel column and recrystallized to obtain a final product.

(1) 화합물 (1-1)의 합성예시 (1) Synthesis Example of Compound (1-1)

Figure 112013041999167-pat00029
Figure 112013041999167-pat00029

13-bromo-7-(4-bromophenyl)-11,11-dimethyl-11H-indeno[2,1-b]perylene (12.0g, 20mmol), diphenylamine (6.8g, 40mmol)을 톨루엔에 넣고 Pd2(dba)3 (1.0g, 1mmol), PPh3 (0.5g, 2mmol), NaOt-Bu (5.8g, 60mmol)을 각각 첨가한 뒤, 100℃에서 24시간 교반하면서 환류시켰다. ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축 한 후 생성된 유기물을 silicagel column 및 재결정하여 최종 생성물인 화합물 (1-1)을 12.3g (수율 79%) 얻었다.
13-bromo-7- (4-bromophenyl) -11,11-dimethyl-11H-indeno [2,1-b] perylene (12.0 g, 20 mmol) and diphenylamine (6.8 g, 40 mmol) were added to toluene and Pd 2 ( dba) 3 (1.0 g, 1 mmol), PPh 3 (0.5 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were added, respectively, and the mixture was refluxed at 100 ° C. for 24 hours with stirring. After extraction with ether and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting organic material was purified by silicagel column and recrystallized to obtain 12.3g (yield 79%) of the final product (1-1).

(2) 화합물 (1-30)의 합성예시(2) Synthesis Example of Compound (1-30)

Figure 112013041999167-pat00030
Figure 112013041999167-pat00030

13-bromo-7-(4-bromophenyl)-11,11-dimethyl-11H-benzo[b]peryleno[3,2-d]silole (12.4g, 20mmol), di([1,1'-biphenyl]-4-yl)amine (12.9g, 40mmol)을 톨루엔에 넣고 Pd2(dba)3 (1.0g, 1mmol), PPh3 (0.5g, 2mmol), NaOt-Bu (5.8g, 60mmol)을 각각 첨가한 뒤, 100℃에서 24시간 교반하면서 환류시켰다. ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축 한 후 생성된 유기물을 silicagel column 및 재결정하여 최종 생성물인 화합물 (1-30)을 15.4g (수율 70%) 얻었다.
13-bromo-7- (4-bromophenyl) -11,11-dimethyl-11H-benzo [b] peryleno [3,2-d] silole (12.4 g, 20 mmol), di ([1,1'-biphenyl] -4-yl) amine (12.9g, 40mmol) was added to toluene and Pd 2 (dba) 3 (1.0g, 1mmol), PPh 3 (0.5 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were added, respectively, and the mixture was refluxed at 100 ° C. for 24 hours with stirring. After extraction with ether and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to obtain 15.4 g (yield 70%) of the final product (1-30).

(3) 화합물 (2-5)의 합성예시(3) Synthesis Example of Compound (2-5)

Figure 112013041999167-pat00031
Figure 112013041999167-pat00031

2,13-dibromo-15,15,18,18-tetramethyl-15,18-dihydrodiindeno[2,1-b:1',2'-n]perylene (12.8g, 20mmol), 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (11.4g, 40mmol)을 톨루엔에 넣고 Pd2(dba)3 (1.0g, 1mmol), PPh3 (0.5g, 2mmol), NaOt-Bu (5.8g, 60mmol)을 각각 첨가한 뒤, 100℃에서 24시간 교반하면서 환류시켰다. ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축 한 후 생성된 유기물을 silicagel column 및 재결정하여 최종 생성물인 화합물 (2-5)를 17.5g (수율 83%) 얻었다.
2,13-dibromo-15,15,18,18-tetramethyl-15,18-dihydrodiindeno [2,1-b: 1 ', 2'-n] perylene (12.8 g, 20 mmol), 9,9-dimethyl- N-phenyl-9H-fluoren-2-amine (11.4 g, 40 mmol) was added to toluene and Pd 2 (dba) 3 (1.0 g, 1 mmol), PPh 3 (0.5 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were added, respectively, and the mixture was refluxed at 100 ° C. for 24 hours with stirring. After extraction with ether and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to obtain 17.5g (yield 83%) of the compound (2-5).

(4) 화합물 (2-31)의 합성예시(4) Synthesis Example of Compound (2-31)

Figure 112013041999167-pat00032
Figure 112013041999167-pat00032

2,13-dibromo-15,18-diphenyl-15,18-dihydrophenanthro[9,8-bc:10,1-b'c']dicarbazole (14.8g, 20mmol), diphenylamine (6.8g, 40mmol)을 톨루엔에 넣고 Pd2(dba)3 (1.0g, 1mmol), PPh3 (0.5g, 2mmol), NaOt-Bu (5.8g, 60mmol)을 각각 첨가한 뒤, 100℃에서 24시간 교반하면서 환류시켰다. ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축 한 후 생성된 유기물을 silicagel column 및 재결정하여 최종 생성물인 화합물 (2-31)을 15.0g (수율 82%) 얻었다.
Toluene 2,13-dibromo-15,18-diphenyl-15,18-dihydrophenanthro [9,8-bc: 10,1-b'c '] dicarbazole (14.8g, 20mmol), diphenylamine (6.8g, 40mmol) Put in Pd 2 (dba) 3 (1.0g, 1mmol), PPh 3 (0.5 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were added, respectively, and the mixture was refluxed at 100 ° C. for 24 hours with stirring. After extraction with ether and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to give 15.0 g (yield 82%) of the final product (2-31).

본 발명의 실시예에 따르는 화합물 (1-1) 내지 화합물 (2-33)의 합성 데이터를 아래 표 3에 제시한다.Synthesis data of compounds (1-1) to (2-33) according to the examples of the present invention are shown in Table 3 below.

Figure 112013041999167-pat00033
Figure 112013041999167-pat00033

유기전기소자의 제조평가Manufacturing Evaluation of Organic Electrical Device

실험예Experimental Example (1) 내지  (1) to 실험예Experimental Example (66): 유기 발광 소자의 제작 및 시험 (형광  (66): Fabrication and Test of Organic Light-Emitting Element (Fluorescent 도판트Dopant ))

합성을 통해 얻은 본 발명에 따르는 화합물을 발광층의 도펀트 물질로 사용하여 통상적인 방법에 따라 유기전계 발광소자를 제작하였다. 먼저, 유리 기판에 형성된 ITO층(양극) 위에 우선 정공 주입층으로서 N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine (2-TNATA로 약기함) 막을 진공증착하여 60 nm 두께로 형성하였다. 이어서, 이 막 상에 정공수송 화합물로서 4,4-비스[N-(1-나프틸)-N-페닐아미노]비페닐 (이하 -NPD로 약기함)을 20 nm 두께로 진공 증착하여 정공수송층을 형성하였다. 정공 수송층 상부에 호스트는 9,10-다이(나프탈렌-2-안트라센(ADN))을 사용하였으며, 도펀트는 본 발명에 따르는 화합물을 95:5 중량으로 도핑함으로써 상기 정공 수송층 위에 30nm 두께의 발광층을 증착하였다. 정공 저지층으로 (1,1'-비스페닐)-4-올레이토)비스(2-메틸-8-퀴놀린올레이토)알루미늄(이하 BAlq로 약기함)을 10 nm 두께로 진공증착하고, 전자수송층으로 트리스(8-퀴놀리놀)알루미늄(이하 Alq3로 약칭함)을 40 nm 두께로 성막하였다. 이후, 할로젠화 알칼리 금속인 LiF를 0.2 nm 두께로 증착하고, 이어서 Al을 150 nm의 두께로 증착하여 이 Al/LiF를 음극으로 사용함으로써 유기 전계 발광소자를 제조하였다.
An organic light emitting diode was manufactured according to a conventional method using the compound according to the present invention obtained through synthesis as a dopant material for a light emitting layer. First, on the ITO layer (anode) formed on the glass substrate, N 1- (naphthalen-2-yl) -N 4 , N 4 -bis (4- (naphthalen-2-yl (phenyl) amino) phenyl as a hole injection layer ) -N 1 -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) membrane was vacuum deposited to form a thickness of 60 nm. Subsequently, 4,4-bis [ N- (1-naphthyl) -N -phenylamino] biphenyl (hereinafter abbreviated as -NPD) was vacuum-deposited to a thickness of 20 nm on the film as a hole transporting compound. Formed. The host used 9,10-di (naphthalene-2-anthracene (ADN)) on top of the hole transport layer, and the dopant deposited a 30 nm thick light emitting layer on the hole transport layer by doping the compound according to the present invention at 95: 5 weight. It was. As a hole blocking layer, (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm, and the electron transport layer Tris (8-quinolinol) aluminum (hereinafter abbreviated to Alq 3 ) was deposited to a thickness of 40 nm. Subsequently, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm, and then Al was deposited to a thickness of 150 nm to prepare an organic EL device by using the Al / LiF as a cathode.

비교예Comparative example (1) (One)

상기 실험예와 동일하게 유기 발광 소자를 제작 및 시험하였으나, 다만 정공 수송층 도펀트 물질로서 본 발명에 따르는 화합물 대신 비교 화합물 A를 사용하였다. An organic light emitting device was manufactured and tested in the same manner as in Experimental Example, except that Comparative Compound A was used instead of the compound according to the present invention as the hole transport layer dopant material.

비교 화합물 AComparative Compound A

Figure 112013041999167-pat00034
Figure 112013041999167-pat00034

비교예Comparative example (2) (2)

상기 실험예와 동일하게 유기 발광 소자를 제작 및 시험하였으나, 다만 정공 수송층 도펀트 물질로서 본 발명에 따르는 화합물 대신 비교 화합물 B를 사용하였다. An organic light emitting device was manufactured and tested in the same manner as in Experimental Example, except that Comparative Compound B was used instead of the compound according to the present invention as the hole transport layer dopant material.

비교 화합물 BComparative Compound B

Figure 112013041999167-pat00035
Figure 112013041999167-pat00035

비교예Comparative example (3) (3)

상기 실험예와 동일하게 유기 발광 소자를 제작 및 시험하였으나, 다만 정공 수송층 도펀트 물질로서 본 발명에 따르는 화합물 대신 비교 화합물 C를 사용하였다. An organic light emitting device was manufactured and tested in the same manner as in Experimental Example, except that Comparative Compound C was used instead of the compound according to the present invention as the hole transport layer dopant material.

비교 화합물 CComparative Compound C

Figure 112013041999167-pat00036
Figure 112013041999167-pat00036

[결과 대비][Contrast result]

이와 같이 제조된 실험예 및 비교예에 따라 제작된 유기전기발광소자들에 순바이어스 직류전압을 가하여 포토리서치(photoresearch)사의 PR-650으로 전기발광(EL) 특성을 측정하였으며, 그 측정 결과 500cd/m2 기준 휘도에서 맥사이언스사에서 제조된 수명 측정 장비를 통해 T95 수명을 측정하였다. 소자제작 및 평가한 결과를 아래 표 4에 나타낸다.The electroluminescent (EL) characteristics were measured by the PR-650 of photoresearch by applying a forward bias DC voltage to the organic electroluminescent devices manufactured according to the experimental and comparative examples thus prepared, and the measurement result was 500 cd / The T95 lifetime was measured using a life measurement instrument manufactured by McScience Inc. at m2 reference luminance. The device fabrication and evaluation results are shown in Table 4 below.

Figure 112013041999167-pat00037
Figure 112013041999167-pat00037

Figure 112013041999167-pat00038
Figure 112013041999167-pat00038

상기 표 4의 결과로부터 알 수 있듯이, 본 발명에 따르는 화합물을 유기전기발광소자용 재료로 이용한 유기전기발광소자는 발광층 재료로 사용되어 높은 발광효율, 낮은 구동전압 및 수명을 현저히 개선시킬 수 있다. As can be seen from the results of Table 4, the organic electroluminescent device using the compound according to the present invention as an organic electroluminescent device material can be used as the light emitting layer material can significantly improve the high luminous efficiency, low driving voltage and lifespan.

다시 말해, 안트라센이 코어인 비교화합물 (1), 퍼릴렌이 코어인 비교화합물 (2)와 비교화합물 (3) 보다 퍼릴렌에 헤테로고리 및 탄소고리가 축합된 형태가 코어인 본 발명에 따르는 화합물이 더 좋은 결과를 나타냈다. 이는 퍼릴렌에 헤테로 고리 및 탄소고리가 축합되면서 원래 퍼릴렌의 에너지값과 달라지게 되는데, 이 달라진 에너지값이 이웃한 층과 에너지 balance를 이뤄 향상된 결과를 초래했다고 설명할 수 있다. In other words, a compound according to the present invention in which a heterocyclic ring and a carbon ring are condensed in a perylene as a comparative compound (1) having an anthracene core, a comparative compound (2) having a perylene core, and a comparative compound (3) This gave a better result. This is due to the condensation of hetero rings and carbon rings in perylene, which is different from the original perylene energy value, which can be explained by the improved energy balance between neighboring layers.

이상의 설명은 본 발명을 예시적으로 설명한 것에 불과한 것으로, 본 발명이 속하는 기술분야에서 통상의 지식을 가지는 자라면 본 발명의 본질적인 특성에서 벗어나지 않는 범위에서 다양한 변형이 가능할 것이다. 따라서, 본 명세서에 개시된 실시 예들은 본 발명을 한정하기 위한 것이 아니라 설명 하기 위한 것이고, 이러한 실시 예에 의하여 본 발명의 사상과 범위가 한정되는 것은 아니다. The above description is merely illustrative of the present invention, and those skilled in the art to which the present invention pertains may various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed herein are not intended to limit the present invention but to describe the present invention, and the spirit and scope of the present invention are not limited thereto.

본 발명의 화합물들을 유기전기발광소자의 다른 유기물층들, 예를 들어 발광 Compounds of the present invention can be used in other organic material layers of organic electroluminescent

보조층, 전자주입층, 전자수송층, 및 정공주입층에 사용되더라도 동일한 효과를 얻을 수 있을 것이다.The same effect may be obtained even when used in the auxiliary layer, the electron injection layer, the electron transport layer, and the hole injection layer.

이상의 설명은 본 발명을 예시적으로 설명한 것에 불과한 것으로, 본 발명이 속하는 기술분야에서 통상의 지식을 가지는 자라면 본 발명의 본질적인 특성에서 벗어나지 않는 범위에서 다양한 변형이 가능할 것이다. 따라서, 본 명세서에 개시된 실시예들은 본 발명을 한정하기 위한 것이 아니라 설명하기 위한 것이고, 이러한 실시예에 의하여 본 발명의 사상과 범위가 한정되는 것은 아니다. 본 발명의 보호범위는 아래의 청구범위에 의하여 해석되어야 하며, 그와 동등한 범위 내에 있는 모든 기술은 본 발명의 권리범위에 포함하는 것으로 해석되어야 할 것이다.The above description is merely illustrative of the present invention, and those skilled in the art to which the present invention pertains may various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed herein are not intended to limit the present invention but to describe the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The protection scope of the present invention should be interpreted by the following claims, and all the technologies within the equivalent scope should be interpreted as being included in the scope of the present invention.

100: 유기전기소자 110: 기판
120: 제 1전극 130: 정공주입층
140: 정공수송층 141: 버퍼층
150: 발광층 151: 발광보조층
160: 전자수송층 170: 전자주입층
180: 제 2전극100: organic electric element 110: substrate
120: first electrode 130: hole injection layer
140: hole transport layer 141: buffer layer
150: light emitting layer 151: light emitting auxiliary layer
160: electron transport layer 170: electron injection layer
180: second electrode

Claims (9)

하기 화학식 (1)로 표시되는 화합물:
화학식 (1)
Figure 112019080940162-pat00039

상기 화학식 (1)에 있어서,
X 및 Y는 각각 독립적으로 CRR, SiRR, NR', O 또는 S이며,
R은 각각 독립적으로 수소; C1~C50의 알킬기; C6~C60의 아릴기; 또는 O, N, S, Si, P 중 적어도 하나의 헤테로원자를 포함하는 C3~C60의 헤테로고리기;이거나, 또는 이웃하는 R의 경우 이들이 서로 결합하여 스파이로 화합물을 형성하며,
R'은 각각 독립적으로 수소; C1~C50의 알킬기; C6~C60의 아릴기; 또는 O, N, S, Si, P 중 적어도 하나의 헤테로원자를 포함하는 C3~C60의 헤테로고리기;이며,
n=0 또는 1의 정수이며,
Ar1 내지 Ar4는 각각 서로 독립적으로 C6~C60의 아릴기; O, N, S, Si, P 중 적어도 하나의 헤테로원자를 포함하는 C3~C60의 헤테로고리기; C1~C50의 알킬기; 또는 플루오렌기;이며,
p, q, r, 및 s는 0 내지 3의 정수이며,
R1 내지 R4는, 상기 p, q, r, 및 s가 2 이상인 경우 각각 복수로서 서로 동일하거나 상이하며, 서로 독립적으로 중수소; C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리와 C6~C60의 방향족고리의 융합고리기; C1~C50의 알킬기; C2~C20의 알켄일기; C2~C20의 알킨일기; C1~C30의 알콕실기; 및 C6~C30의 아릴옥시기로 이루어진 군에서 선택되거나, 또는 이들이 각각 서로 결합하여 고리를 형성하며,
R5 및 R6은 서로 독립적으로 수소; 중수소; C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리와 C6~C60의 방향족고리의 융합고리기; C1~C50의 알킬기; C2~C20의 알켄일기; C2~C20의 알킨일기; C1~C30의 알콕실기; 및 C6~C30의 아릴옥시기로 이루어진 군에서 선택되며,
상기 아릴기, 플루오렌일기, 헤테로고리기, 융합고리기, 알킬기, 알켄일기, 알킨일기, 알콕실기, 아릴옥시기는 중수소, 할로겐, 실란기, 실록산기, 붕소기, 게르마늄기, 시아노기, 니트로기, C1~C20의 알킬싸이오기, C1~C20의 알콕실기, C1~C20의 알킬기, C2~C20의 알켄일기, C2~C20의 알킨일기, C6~C20의 아릴기, 중수소로 치환된 C6~C20의 아릴기, 플루오렌일기, C2~C20의 헤테로고리기, C3~C20의 시클로알킬기, C7~C20의 아릴알킬기, 및 C8~C20의 아릴알켄일기로 이루어진 군에서 선택된 하나 이상의 치환기로 더욱 치환될 수 있음.Compound represented by the following formula (1):
Formula (1)
Figure 112019080940162-pat00039

In the above formula (1),
X and Y are each independently CRR, SiRR, NR ', O or S,
Each R is independently hydrogen; C 1 ~ C 50 Alkyl group; C 6 ~ C 60 Aryl group; Or a C 3 to C 60 heterocyclic group including at least one hetero atom of O, N, S, Si, or P; or, in the case of a neighboring R, they combine with each other to form a spiro compound,
Each R ′ is independently hydrogen; C 1 ~ C 50 Alkyl group; C 6 ~ C 60 Aryl group; Or a C 3 to C 60 heterocyclic group including at least one hetero atom of O, N, S, Si, or P;
is an integer of n = 0 or 1,
Ar 1 to Ar 4 are each independently of the other C 6 ~ C 60 An aryl group; C 3 ~ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si, P; C 1 ~ C 50 Alkyl group; Or a fluorene group;
p, q, r, and s are integers from 0 to 3,
R 1 to R 4 are the same as or different from each other as a plurality when p, q, r, and s are 2 or more, and are each independently deuterium; C 6 ~ C 60 Aryl group; Fluorenyl groups; C 2 ~ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C 3 ~ C 60 of aliphatic rings and C 6 ~ C 60; C 1 ~ C 50 Alkyl group; C 2 ~ C 20 Alkenyl group; Alkynyl groups of C 2 to C 20 ; C 1 -C 30 alkoxyl group; And C 6 ~ C 30 It is selected from the group consisting of an aryloxy group, or they are combined with each other to form a ring,
R 5 and R 6 are each independently hydrogen; heavy hydrogen; C 6 ~ C 60 Aryl group; Fluorenyl group; C 2 ~ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; A fused ring group of an aliphatic ring of C 3 ~ C 60 and an aromatic ring of C 6 ~ C 60 ; C 1 ~ C 50 Alkyl group; C 2 ~ C 20 Alkenyl group; Alkynyl groups of C 2 to C 20 ; An alkoxyl group of C 1 to C 30 ; And it is selected from the group consisting of C 6 ~ C 30 aryloxy group,
The aryl group, fluorenyl group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxyl group, aryloxy group deuterium, halogen, silane group, siloxane group, boron group, germanium group, cyano group, nitro group, C 1 ~ C 20 coming of the alkylthio, C 1 ~ C 20 alkoxy group, C 1 ~ C 20 alkenyl in the alkyl group, C 2 ~ C 20 of the diary, C 2 ~ C 20 alkynyl, C 6 ~ of C 20 aryl group, C 6 ~ C 20 aryl group substituted with deuterium, fluorenyl group, C 2 ~ C 20 heterocyclic group, C 3 ~ C 20 cycloalkyl group, C 7 ~ C 20 arylalkyl group And it may be further substituted with one or more substituents selected from the group consisting of C 8 ~ C 20 arylalkenyl group. 제 1 항에 있어서, 상기 화합물은 하기 화학식 (2) 또는 화학식 (3)으로 표시되는 것을 특징으로 하는 화합물:
화학식 (2)
Figure 112019080940162-pat00040

화학식 (3)
Figure 112019080940162-pat00041
.
상기 화학식 (2) 및 화학식 (3)에 있어서, X, Y, Ar1 내지 Ar4, p, q, r, s 및 R1 내지 R6는 상기 화학식 (1)에서 정의한 것과 동일하다.
The compound according to claim 1, wherein the compound is represented by the following formula (2) or formula (3):
Formula (2)
Figure 112019080940162-pat00040

Formula (3)
Figure 112019080940162-pat00041
.
In the above formulas (2) and (3), X, Y, Ar 1 to Ar 4 , p, q, r, s and R 1 to R 6 are the same as defined in the formula (1).
제 1 항에 있어서, 상기 화합물은 화학식 (1-1) 내지 화학식 (2-33) 중 어느 하나로 표시됨을 특징으로 하는 화합물:
Figure 112019080940162-pat00042

Figure 112019080940162-pat00043

Figure 112019080940162-pat00044
.The compound of claim 1, wherein the compound is represented by any one of formulas (1-1) to (2-33):
Figure 112019080940162-pat00042

Figure 112019080940162-pat00043

Figure 112019080940162-pat00044
. 제 1 전극, 제 2 전극, 및 상기 제 1 전극과 제 2 전극 사이에 위치하는 유기물층을 포함하는 유기전기소자에 있어서,
상기 유기물층은 제 1 항 내지 제 3 항 중 어느 한 항의 화합물을 함유하는 것을 특징으로 하는 유기전기소자.In an organic electroluminescent device comprising a first electrode, a second electrode, and an organic material layer positioned between the first electrode and the second electrode,
The organic material layer is characterized in that it contains a compound of any one of claims 1 to 3. 제 4 항에 있어서, 상기 제 1 전극의 하부 또는 제 2 전극의 상부 중 적어도 하나에 광효율 개선층을 더욱 포함하는 유기전기소자.The organic electronic device of claim 4, further comprising a light efficiency improving layer on at least one of the lower part of the first electrode and the upper part of the second electrode. 제 4 항에 있어서, 상기 화합물을 용액공정(soluble process)에 의해 상기 유기물층으로 형성하는 것을 특징으로 하는 유기전기소자.The organic electroluminescent device according to claim 4, wherein the compound is formed into the organic material layer by a soluble process. 제 4 항에 있어서, 발광층의 도펀트 물질로서 상기 화합물을 함유하는 것을 특징으로 하는 유기전기소자.The organic electroluminescence device according to claim 4, wherein the compound is contained as a dopant material of the light emitting layer. 제 4 항의 유기전기소자를 포함하는 디스플레이장치; 및
상기 디스플레이장치를 구동하는 제어부; 를 포함하는 전자장치.A display device comprising the organic electroluminescent element of claim 4; And
A controller for driving the display device; Electronic device comprising a. 제 8 항에 있어서, 상기 유기전기소자는 유기전기발광소자(OLED ), 유기태양전지, 유기감광체(OPC), 유기트랜지스터(유기 TFT), 및 단색 또는 백색 조명용 소자 중 적어도 하나인 것을 특징으로 하는 전자장치.The method of claim 8, wherein the organic electroluminescent device is at least one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a device for monochrome or white illumination. Electronics.
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