KR102466522B1 - Compound for organic electronic element having benzocyclobutene functional group for cross-linked bond, organic electronic element using the same, and an electronic device thereof - Google Patents

Compound for organic electronic element having benzocyclobutene functional group for cross-linked bond, organic electronic element using the same, and an electronic device thereof Download PDF

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KR102466522B1
KR102466522B1 KR1020200168766A KR20200168766A KR102466522B1 KR 102466522 B1 KR102466522 B1 KR 102466522B1 KR 1020200168766 A KR1020200168766 A KR 1020200168766A KR 20200168766 A KR20200168766 A KR 20200168766A KR 102466522 B1 KR102466522 B1 KR 102466522B1
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이성구
배승환
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Abstract

본 발명은 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물로서, 그 말단에 적어도 하나 이상의 벤조시클로부텐기(benzocyclobutene)를 포함하는 것을 특징으로 한다. The present invention is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric device, and is characterized in that it includes at least one benzocyclobutene group at its terminal.

Description

가교결합성 벤조시클로부텐기를 갖는 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치{COMPOUND FOR ORGANIC ELECTRONIC ELEMENT HAVING BENZOCYCLOBUTENE FUNCTIONAL GROUP FOR CROSS-LINKED BOND, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF}Compounds for organic electric devices having a cross-linkable benzocyclobutene group, organic electric devices using the same, and electronic devices thereof THEREOF}

본 발명은 OLED 적용에서 사용하기 위한 유기화학 조성물에 관한 것으로서, 특히, 가교결합성 벤조시클로부텐기를 갖는 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치에 관한 것이다. The present invention relates to an organic chemical composition for use in OLED applications, and more particularly, to a compound for an organic electric device having a crosslinkable benzocyclobutene group, 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, the organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic electric device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often composed of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic electric device, and may include, for example, 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. Materials used as organic layers in organic electric devices may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, according to their functions.

본 발명에서 사용되는 용어 '유기전기소자'는, 유기 집적 회로(OIC), 유기 전계-효과 트랜지스터(OFET), 유기 박막 트랜지스터(OTFT), 유기 발광 트랜지스터(OLET), 유기 태양 전지(OSC), 유기 광검출기, 유기 광수용체, 유기 전계-켄치 소자(OFQD), 유기 발광 전기화학 전지(OLEC), 유기 레이저 다이오드(O-laser) 및 유기 전계 발광 소자(OLED) 등을 포함하는 것으로 정의된다. The term 'organic electric device' used in the present invention includes an organic integrated circuit (OIC), an organic field-effect transistor (OFET), an organic thin film transistor (OTFT), an organic light emitting transistor (OLET), an organic solar cell (OSC), Organic photodetectors, organic photoreceptors, organic field-quench devices (OFQDs), organic light emitting electrochemical cells (OLECs), organic laser diodes (O-lasers) and organic electroluminescent devices (OLEDs), and the like are defined.

본 발명에서는 특히, OLED로서 지칭되는 유기전기소자에 사용되는 신규한 유기화합물을 제공하는 것에 관심이 있다. OLED의 일반 구조 및 이의 기능적 원리는 당업자에게 널리 공지되어 있고, 특히 US 4539507, US 5151629, EP 0676461 및 WO 1998/27136에 기재되어 있다. In the present invention, we are particularly interested in providing novel organic compounds used in organic electric devices referred to as OLEDs. The general structure of OLEDs and their functional principles are well known to the person skilled in the art and are described in particular in US Pat. No. 4,539,507, US Pat. No. 5,151,629, EP 0676461 and WO 1998/27136.

차세대 디스플레이 디바이스로 주목받고 있는 OLED(organic photoelectric device)는 ITO와 같은 투명 양극재가 코팅된 기판과 음극 사이에 유기발광층을 형성하여, 전극에 소정의 전압을 가하면 양극으로부터 주입된 정공과 음극으로부터 주입된 전자가 유기발광층에서 결합하여 빛을 방출하는 원리를 이용한 소자이다. OLED는 평판 디스플레이, 조명 및 백라이팅과 같은 전자 장치에 응용되면서 점점 관심을 받고 있다. OLED 기술은 Geffroy 등의, "유기 발광 다이오드 (OLED) 기술: 재료 소자 및 디스플레이 기술", Polym, Int., 55:572-582(2006)에서 설명되며, 미국 특허 제 5,844,363 호, 제 6,303,238 호 및 제 5,707,745 호에서 설명된 여러 OLED 재료 및 구성에서 설명되고, 이들 모두는 본 명세서에 참고로 인용된다. OLED (organic photoelectric device), which is attracting attention as a next-generation display device, forms an organic light emitting layer between a substrate coated with a transparent anode material such as ITO and a cathode, and when a predetermined voltage is applied to the electrode, holes injected from the anode and holes injected from the cathode It is a device using the principle of emitting light by combining electrons in the organic light emitting layer. OLEDs are increasingly gaining attention as they are applied to electronic devices such as flat panel displays, lighting and backlighting. OLED technology is described in Geffroy et al., “Organic Light Emitting Diode (OLED) Technology: Materials Device and Display Technology,” Polym, Int., 55:572-582 (2006), U.S. Pat. Nos. 5,844,363, 6,303,238 and 5,707,745 is described in several OLED materials and constructions, all of which are incorporated herein by reference.

유기 전계 발광 소자(OLED)는 산업적으로 적용 가능한 수준의 성능을 구현하기 위하여 유기발광층 이외에 정공주입층, 정공수송층, 전자수송층, 전자주입층 및 발광층의 특성에 따라 전하차단층을 더 포함하여 다층 구조로 제작된다. The organic electroluminescent device (OLED) has a multi-layer structure including a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, and a charge blocking layer according to the characteristics of the light emitting layer in addition to the organic light emitting layer to realize industrially applicable performance. is made with

종래기술에서 유기전기소자(특히, OLED)를 구성하는 각 층들은 일반적으로 진공증착공정에 의해 형성된다. 일본 공개특허 제 2006-156847 호(특허문헌 1)는 유기 화합물 및 이를 진공증착법으로 기판에 증착시켜 단층구조의 유기막을 포함하는 유기전기소자를 제조하는 기술을 개시하고 있다. 진공증착법은 10-4 Torr 이하의 고진공 분위기에서 시료에 열을 가하여 승화시키고, 승화된 시료는 상대적으로 낮은 온도의 기판에서 고체로 성장하는 방식으로 박막을 형성시키는 원리이다. 그러나, 진공증착법은 증착장치가 크고 설치가 용이하지 못하며, 공정시 진공을 유지해야 하고, 공정 온도가 높으며, 특히 패턴을 위해 마스크를 사용하기 때문에 재료의 소비율이 높아 생산성이 낮고 제조비용이 많이 소비되기 때문에 대면적으로 유기전기소자를 제조하기 어렵다. In the prior art, each layer constituting an organic electric device (in particular, an OLED) is generally formed by a vacuum deposition process. Japanese Patent Laid-Open No. 2006-156847 (Patent Document 1) discloses an organic compound and a technique for manufacturing an organic electric device including a single-layered organic film by depositing the same on a substrate by a vacuum deposition method. The vacuum deposition method is a principle of forming a thin film by applying heat to a sample in a high vacuum atmosphere of 10 -4 Torr or less to sublimate it, and the sublimated sample grows into a solid on a substrate at a relatively low temperature. However, the vacuum deposition method has a large deposition device and is not easy to install, requires a vacuum to be maintained during the process, a high process temperature, and in particular, because a mask is used for the pattern, the material consumption rate is high, so the productivity is low and the manufacturing cost is high. Therefore, it is difficult to manufacture an organic electric element in a large area.

이러한 문제점을 해소하기 위하여 저가의 용액공정을 통해 유기박막을 형성하고자 하는 연구가 꾸준히 진행되어왔다. 용액공정은 진공증착 공정에 비해 분해능이 높지 않은 단점이 있지만, 대기압과 대기 온도에서 제조가 가능하기 때문에 별도의 진공장치가 필요하지 않으며, 재료의 소비율이 낮기 때문에, 생산성이 높고, 제조비용이 적게 들며, 대면적화가 가능한 것이 장점이다.In order to solve this problem, research to form an organic thin film through a low-cost solution process has been steadily progressing. The solution process has the disadvantage of not having high resolution compared to the vacuum deposition process, but it does not require a separate vacuum device because it can be manufactured at atmospheric pressure and temperature. Its advantage is that it can be scaled to a large area.

이와 같은 용액공정의 종류에는 스핀 코팅, 잉크젯 코팅, 스크린 프린팅, 스프레이 코팅, 롤 투 롤 코팅, 그리고 블레이드 코팅 등이 있다. 용액공정을 기반으로 한 대면적 유기 박막 제조 방법 및 그 장치에 대한 구체적인 예들은 대한민국 공개특허공보 제 2016-0069799 호, 대한민국 등록특허공보 제 10-1618395 호, 대한민국 공개특허공보 제 2017-0066703 호, 대한민국 등록특허공보 제 10-1618395 호, 대한민국 공개특허공보 제 2016-0141127 호 및 대한민국 공개특허공보 제 2016-0138845 호에 상세되어 있다. 또한, 사용될 수 있는 열프린팅 기술 및 장치는 예를 들면 미국 특허 출원 공개 US 2008/0311307 A1, US 2008/0308037 A1, US2006/0115585 A1, US 2010/0188457 A1, US 2011/0008541 A1, US 2010/0171780 A1, 및 US 2010/0201749 A1에 설명된 것들을 포함하며, 그 전체가 본 명세서에 참고로 인용된다.Types of such solution processes include spin coating, inkjet coating, screen printing, spray coating, roll-to-roll coating, and blade coating. Specific examples of a method for manufacturing a large-area organic thin film based on a solution process and a device therefor include Korean Patent Publication No. 2016-0069799, Korean Patent Registration No. 10-1618395, Korean Patent Publication No. 2017-0066703, Korean Patent Registration No. 10-1618395, Korean Patent Publication No. 2016-0141127 and Korean Patent Publication No. 2016-0138845 are detailed. Thermal printing techniques and devices that can also be used are described in, for example, published US patent applications US 2008/0311307 A1, US 2008/0308037 A1, US2006/0115585 A1, US 2010/0188457 A1, US 2011/0008541 A1, US 2010/ 0171780 A1, and US 2010/0201749 A1, which are incorporated herein by reference in their entirety.

그러나, 용액공정을 이용하여 유기전기소자용 다층 유기막을 코팅할 때, 위층의 유기 화합물에 포함된 유기용매에 의해 아래층의 유기박막이 손상되는 문제가 있어 다층 박막을 형성함에 어려움이 있다. 이를 해결하기 위해서는 가교가 가능한 작용기를 가지는 유기 화합물을 사용해야 하는데, 이제까지 알려진 가교기들은 스티렌(styrene), 아크릴레이트(acrylate), 옥세탄(oxetane) 등이다. 그러나, 이들 가교기들은 가교반응을 위해 높은 가교온도를 요구하고 있어서 플라스틱 기판을 사용하는데 있어 어려움이 있다. 또한, 자외선 가교의 경우에는 광개시제를 사용하거나 부산물(byproduct)이 발생하여 유기전기소자의 수명과 효율에 문제를 발생시키는 단점이 있다. However, when coating a multilayer organic film for an organic electric device using a solution process, there is a problem in that the organic thin film of the lower layer is damaged by the organic solvent included in the organic compound of the upper layer, making it difficult to form the multilayer thin film. In order to solve this problem, an organic compound having a crosslinkable functional group must be used, and known crosslinking groups include styrene, acrylate, oxetane, and the like. However, since these crosslinking groups require a high crosslinking temperature for the crosslinking reaction, it is difficult to use a plastic substrate. In addition, in the case of UV crosslinking, there is a disadvantage in that a photoinitiator is used or a byproduct is generated, causing problems in the lifespan and efficiency of the organic electric device.

한편, 벤조시클로부텐(BCB : Benzocyclobutene)기는, 전형적으로 200℃ 이상에서 열적으로 활성화된 이량체화를 경험하는 일 부분의 예이고, 이 경우에, 시클로부텐의 C-C 결합 중 하나의 절단에 의해 형성된, 디벤조시클로옥타디엔 고리를 형성하고, 그 다음 비가역적 고리화가 부가된다. 이러한 시클로부텐 고리에서, 산소-기반 공여체의 치환이 BCB의 개환 온도에 관해 극적 효과를 가짐이 공개 문헌(Dobish, JN; Hamilton, SK; Harth, EPolymer Chemistry 2012, 3, 857-860)에서 문서로 기록되어 있다. 그러나, 이 현상은 OLED 적용에 아직 이용되지 않고 있다. On the other hand, the benzocyclobutene (BCB: Benzocyclobutene) group is an example of a part that undergoes thermally activated dimerization, typically above 200 ° C., in this case, formed by cleavage of one of the C-C bonds of cyclobutene, A dibenzocyclooctadiene ring is formed, followed by irreversible cyclization. In this cyclobutene ring, it is documented in the published literature (Dobish, JN; Hamilton, SK; Harth, EPolymer Chemistry 2012, 3, 857-860) that substitution of the oxygen-based donor has a dramatic effect on the ring-opening temperature of the BCB. It is recorded. However, this phenomenon has not yet been exploited for OLED applications.

OLED에서 벤조시클로부텐(BCB) 화학 및 그의 용도는 하기 공개 문헌들에서 기재된다: US20040004433, US20080315757, US20080309229, US20100133566, US20110095278, US20110065222, US20110198573, US20110042661, JP2010062120, US7893160, US20110089411, US20070181874, US20070096082, CN102329411, US20120003790, WO2012052704, WO2012175975, WO2013007966, 국제출원 PCT/CN14/084918(8/21/14 출원), US 가출원 62/039935(8/21/14 출원)OLED에서 벤조시클로부텐(BCB) 화학 및 그의 용도는 하기 공개 문헌들에서 기재된다: US20040004433, US20080315757, US20080309229, US20100133566, US20110095278, US20110065222, US20110198573, US20110042661, JP2010062120, US7893160, US20110089411, US20070181874, US20070096082, CN102329411, US20120003790 , WO2012052704, WO2012175975, WO2013007966, international application PCT/CN14/084918 (filed on 8/21/14), US provisional application 62/039935 (filed on 8/21/14)

특히, 대한민국 공개특허공보 제 2017-0043557 호(특허문헌 2)는 OLED 적용에서 사용을 위하여 가교결합성 BCB-작용화된 물질을 포함하는 조성물을 제공한다. 특허문헌 2의 조성물은 전계발광(electroluminescent) 디바이스에서 사용을 위하여 정공 전달(hole-transporting) 물질을 형성하기 위해 사용될 수 있다. 특히, 특허문헌 2는 아래의 [구조 A]로부터 선택된 적어도 하나의 화합물을 포함하는 조성물을 제공한다. 즉, 아래 [구조 A]로부터 선택된 적어도 하나의 화합물을 포함하는 조성물은 벤조시클로부텐으로 치환된 카르바졸을 함유하는 조성물일 수 있다. In particular, Korean Patent Publication No. 2017-0043557 (Patent Document 2) provides a composition comprising a crosslinkable BCB-functionalized material for use in OLED applications. The composition of Patent Document 2 can be used to form a hole-transporting material for use in an electroluminescent device. In particular, Patent Document 2 provides a composition containing at least one compound selected from [Structure A] below. That is, a composition containing at least one compound selected from [Structure A] below may be a composition containing carbazole substituted with benzocyclobutene.

Figure 112020131688418-pat00001
Figure 112020131688418-pat00001

[구조 A][Structure A]

그러나, 가교결합성 BCB-작용화된 물질을 포함하는 OLED 적용에서 사용을 위한 새롭고도 신규한 유기전기소자용 화합물의 필요성은 여전하다. 이들 필요성은 본 발명에 의하여 충족되고 있다. However, there is still a need for new and novel compounds for organic electronics for use in OLED applications that include crosslinkable BCB-functionalized materials. These needs are met by the present invention.

JPJP 2006-1568472006-156847 AA KRKR 2017-00435572017-0043557 AA

"유기 발광 다이오드 (OLED) 기술 : 재료 소자 및 디스플레이 기술", Polym, Int., 55:572-582(2006)"Organic Light Emitting Diode (OLED) Technology: Material Device and Display Technology", Polym, Int., 55:572-582(2006) Dobish, JN; Hamilton, SK; Harth, EPolymer Chemistry 2012, 3, 857-860Dobish, JN; Hamilton, SK; Harth, EP Polymer Chemistry 2012, 3, 857-860

본 발명이 이루고자 하는 기술적 과제는 OLED 적용에 사용하기 적합한 가교결합성 BCB-작용화된 물질을 포함하는 새롭고도 신규한 유기전기소자용 화합물을 제공하는 것이다. The technical problem to be achieved by the present invention is to provide a new and novel compound for an organic electric device comprising a crosslinkable BCB-functionalized material suitable for use in OLED applications.

또한, 본 발명은 120℃ 이하의 낮은 온도에서 가교가 가능하고, 부산물(byproduct)을 발생시키지 않아 효율과 수명 특성이 우수한 신규한 유기전기소자용 화합물 및 이 화합물을 제조하는 방법을 제공하는 것이다. In addition, the present invention is to provide a novel compound for an organic electric device that can be crosslinked at a low temperature of 120° C. or less, does not generate byproducts, and has excellent efficiency and lifespan characteristics, and a method for preparing the compound.

특히, 본 발명은 120℃ 정도의 낮은 온도에서 가열을 통해 가교결합이 발생되고, 이로 인해 유기용매에 용해되지 않는 유기전기소자용 유기박막을 제공하는 것을 다른 일 목적으로 한다. In particular, another object of the present invention is to provide an organic thin film for an organic electric device in which crosslinking occurs through heating at a low temperature of about 120° C., and thus is insoluble in an organic solvent.

또한, 본 발명은 이러한 유기박막을 다층 적층하여 형성되는 OLED를 포함하는 유기전기소자 및 이 유기전기소자를 포함하는 전자장치를 제공하는 것을 또 다른 일 목적으로 한다. Another object of the present invention is to provide an organic electric device including an OLED formed by laminating such organic thin films in multiple layers, and an electronic device including the organic electric device.

본 발명이 이루고자 하는 기술적 과제는 이상에서 언급한 기술적 과제로 제한되지 않으며, 언급되지 않은 또 다른 기술적 과제들은 아래의 기재로부터 본 발명이 속하는 기술 분야에서 통상의 지식을 가진 자에게 명확하게 이해될 수 있을 것이다.The technical problem to be achieved by the present invention is not limited to the above-mentioned technical problem, and other technical problems not mentioned can be clearly understood by those skilled in the art from the description below. There will be.

상기한 기술적 과제를 달성하기 위한 본 발명의 제 1 양태는 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물으로서,상기 유기화합물은, 아래 [구조식 A]로부터 선택된 적어도 하나의 화합물을 포함하는 것을 특징으로 한다. A first aspect of the present invention for achieving the above technical problem is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric device, the organic compound is, the following [structural formula A] Characterized in that it comprises at least one compound selected from.

[구조식 A][Structural Formula A]

Figure 112020131688418-pat00002
Figure 112020131688418-pat00002

상기 [구조식 A]에서, R1, R2는 서로 같거나 상이하고, 각각 독립적으로 수소, 알킬기(alkyl group), 치환된 알킬기(alkyl group), 헤테로사이클로기(heterocyclic group), 치환된 헤테로사이클로기(heterocyclic group), 아릴기(aryl group), 치환된 아릴기(aryl group), 아민기(amine group), 피리딘기(pyridine group), 피리미딘기(pyrimidine group), 트이라졸기(triazole group), 트리아진기(triazine group), 포스파인기(phosphine group), 시릴기(silole group), 아릴아민기(arylamine), 카바졸기(carbazole) 또는 치환된 카바졸기로부터 선택되고; In [Formula A], R 1 and R 2 are the same as or different from each other, and each independently represents hydrogen, an alkyl group, a substituted alkyl group, a heterocyclic group, or a substituted heterocycle. Heterocyclic group, aryl group, substituted aryl group, amine group, pyridine group, pyrimidine group, triazole group ), a triazine group, a phosphine group, a silole group, an arylamine group, a carbazole group, or a substituted carbazole group;

상기 X1, X2는 서로 같거나 상이하고, 각각 독립적으로 알킬기(alkyl group), 치환된 알킬기(alkyl group), 헤테로사이클로기(heterocyclic group), 치환된 헤테로사이클로기(heterocyclic group)로부터 선택될 수 있고; The X 1 and X 2 are the same as or different from each other, and each independently selected from an alkyl group, a substituted alkyl group, a heterocyclic group, and a substituted heterocyclic group. can;

상기 R1, R2, X1, X2중 선택된 적어도 1곳 이상에는 아래 [구조식 B]의 벤조시클로부텐기(benzocyclobutene)가 직접 적용되거나 수소, 알킬기(alkyl group), 치환된 알킬기(alkyl group), 헤테로사이클로기(heterocyclic group), 치환된 헤테로사이클로기(heterocyclic group), 아릴기(aryl group), 치환된 아릴기(aryl group), 아민기(amine group)에 아래 [구조식 B]의 벤조시클로부텐기(benzocyclobutene)로 치환된 유도체가 적용되며;At least one selected from among R 1 , R 2 , X 1 , and X 2 , a benzocyclobutene group of [Structural Formula B] below is directly applied, or hydrogen, an alkyl group, or a substituted alkyl group ), a heterocyclic group, a substituted heterocyclic group, an aryl group, a substituted aryl group, and an amine group below [Formula B] of benzo A derivative substituted with a cyclobutene group (benzocyclobutene) is applied;

[구조식 B][Structural Formula B]

Figure 112020131688418-pat00003
Figure 112020131688418-pat00003

상기 [구조식 B]에서, Y는 수소 또는 탄화수소, 특히, C1~C13의 탄소 체인을 가진 알킬기 또는 치환된 알칼기, 수소, 아민 또는 할로겐을 가지고 있는 알킬기이고, X1, X2, X3, X4, X5는 서로 같거나 상이하고, 각각 독립적으로 수소, 탄화수소, 치환된 탄화수소, 할로겐, 시아노, 니트로, 하이드록실, 알콕시, 아민 또는 치환된 아민, 카보닐로부터 선택된다In [Structural Formula B], Y is hydrogen or a hydrocarbon, in particular, an alkyl group having a carbon chain of C 1 to C 13 or a substituted alkyl group, hydrogen, an amine or an alkyl group having a halogen, X 1 , X 2 , X 3 , X 4 , and X 5 are the same as or different from each other, and are each independently selected from hydrogen, hydrocarbon, substituted hydrocarbon, halogen, cyano, nitro, hydroxyl, alkoxy, amine, substituted amine, or carbonyl.

본 발명의 다른 제 2 양태는, 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물으로서, 아래의 화학식을 갖는 것을 특징으로 한다. Another second aspect of the present invention is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric element, characterized in that it has the following chemical formula.

Figure 112020131688418-pat00004
Figure 112020131688418-pat00004

본 발명의 다른 제 3 양태는, 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물으로서, 아래의 화학식을 갖는 것을 특징으로 한다. Another third aspect of the present invention is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric element, characterized in that it has the following chemical formula.

Figure 112020131688418-pat00005
Figure 112020131688418-pat00005

본 발명의 다른 제 4 양태는, 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물으로서, 아래의 화학식을 갖는 것을 특징으로 한다. Another fourth aspect of the present invention is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric element, characterized in that it has the following chemical formula.

Figure 112020131688418-pat00006
Figure 112020131688418-pat00006

본 발명의 다른 제 5 양태는, 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물으로서, 아래의 화학식을 갖는 것을 특징으로 한다.Another fifth aspect of the present invention is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric element, characterized in that it has the following chemical formula.

Figure 112020131688418-pat00007
Figure 112020131688418-pat00007

본 발명의 다른 제 6 양태는, 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물으로서, 아래의 화학식을 갖는 것을 특징으로 한다.Another sixth aspect of the present invention is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric element, characterized in that it has the following chemical formula.

Figure 112020131688418-pat00008
Figure 112020131688418-pat00008

본 발명의 다른 제 7 양태는, 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물으로서, 아래의 화학식을 갖는 것을 특징으로 한다.Another seventh aspect of the present invention is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric element, characterized in that it has the following chemical formula.

Figure 112020131688418-pat00009
Figure 112020131688418-pat00009

본 발명의 다른 제 8 양태는, 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물으로서, 아래의 화학식을 갖는 것을 특징으로 한다.Another eighth aspect of the present invention is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric element, characterized in that it has the following chemical formula.

Figure 112020131688418-pat00010
Figure 112020131688418-pat00010

본 발명의 다른 제 9 양태는, 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물으로서, 아래의 화학식을 갖는 것을 특징으로 한다.Another ninth aspect of the present invention is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric element, characterized in that it has the following chemical formula.

Figure 112020131688418-pat00011
Figure 112020131688418-pat00011

본 발명의 다른 제 10 양태는, 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물으로서, 아래의 화학식을 갖는 것을 특징으로 한다.Another tenth aspect of the present invention is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric element, characterized in that it has the following chemical formula.

Figure 112020131688418-pat00012
Figure 112020131688418-pat00012

본 발명의 다른 제 11 양태는, 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물으로서, 아래의 화학식을 갖는 것을 특징으로 한다.Another eleventh aspect of the present invention is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric element, characterized in that it has the following chemical formula.

Figure 112020131688418-pat00013
Figure 112020131688418-pat00013

본 발명의 다른 제 12 양태는, 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물으로서, 아래의 화학식을 갖는 것을 특징으로 한다.Another twelfth aspect of the present invention is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric element, characterized in that it has the following chemical formula.

Figure 112020131688418-pat00014
Figure 112020131688418-pat00014

본 발명의 다른 제 13 양태는, 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물으로서, 아래의 화학식을 갖는 것을 특징으로 한다.Another thirteenth aspect of the present invention is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric element, characterized in that it has the following chemical formula.

Figure 112020131688418-pat00015
Figure 112020131688418-pat00015

본 발명의 다른 제 14 양태는, 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물으로서, 아래의 화학식을 갖는 것을 특징으로 한다.Another fourteenth aspect of the present invention is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric element, characterized in that it has the following chemical formula.

Figure 112020131688418-pat00016
Figure 112020131688418-pat00016

본 발명의 다른 제 15 양태는, 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물으로서, 아래의 화학식을 갖는 것을 특징으로 한다.Another fifteenth aspect of the present invention is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric element, characterized in that it has the following chemical formula.

Figure 112020131688418-pat00017
Figure 112020131688418-pat00017

상기 유기화합물은 유기전기소자용 유기박막 재료중 발광층 물질, 정공주입층 물질, 정공수송층 물질, 전자주입층 물질, 전자수송층 물질, 전자차단층 물질 및 정공차단층 물질로 이루어진 군으로부터 선택된 적어도 하나의 용도로 사용되는 것을 특징으로 한다. The organic compound is at least one selected from the group consisting of a light emitting layer material, a hole injection layer material, a hole transport layer material, an electron injection layer material, an electron transport layer material, an electron blocking layer material, and a hole blocking layer material among organic thin film materials for an organic electric device. Characterized in that it is used for a purpose.

본 발명의 또 다른 제 16 양태는, 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 잉크 조성물로서, 상기 잉크 조성물은 상기 제 1 양태 내지 제 15 양태중 선택된 어느 하나의 유기화합물을 포함하는 것을 특징으로 한다. Another sixteenth aspect of the present invention is an ink composition for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric element, wherein the ink composition is any one selected from the first to fifteenth aspects Characterized in that it contains an organic compound of.

상기 잉크 조성물은 용매를 더 포함하는 용액 또는 현탁액인 것을 특징으로 한다. 또한, 상기 잉크 조성물은 안료 또는 염료를 더 포함할 수 있다. The ink composition is characterized in that it is a solution or suspension further containing a solvent. In addition, the ink composition may further include a pigment or dye.

상기 잉크 조성물은 인광 도펀트 또는 형광 도펀트를 더 포함할 수도 있다. The ink composition may further include a phosphorescent dopant or a fluorescent dopant.

본 발명의 또 다른 제 17 양태는, 음극과 양극 사이에 적어도 발광층을 포함하는 일층 또는 복수층으로 이루어지는 유기 박막층이 협지되어 있는 유기전기소자에 있어서, 상기 유기 박막층을 형성하기 위한 유기화합물이 상기 제 1 양태 내지 제 15 양태중 선택된 어느 하나의 유기화합물을 포함하는 것을 특징으로 한다. Another seventeenth aspect of the present invention is an organic electric device in which an organic thin film layer comprising one or a plurality of layers including at least a light emitting layer is sandwiched between a cathode and an anode, wherein the organic compound for forming the organic thin film layer is It is characterized by including the organic compound of any one selected from the 1st aspect to the 15th aspect.

상기 유기 박막층을 형성하는 유기화합물의 말단의 벤조시클로부텐기(benzocyclobutene)간에 가교결합이 형성된다. Cross-linking is formed between benzocyclobutene groups at the ends of organic compounds forming the organic thin film layer.

상기 유기 박막층은 발광층, 정공주입층, 정공수송층, 전자주입층, 전자수송층, 전자차단층 및 정공차단층으로 이루어진 군으로부터 선택된 적어도 하나이고, 양극, 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 및 음극이 이 순서대로 적층된 구조를 갖는다. The organic thin film layer is at least one selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer, and an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, It has a structure in which an electron injection layer and a cathode are stacked in this order.

또한, 상기 유기 박막층은 상기 유기화합물을 포함하는 잉크 조성물을 용액 공정에 의해 도포하고 건조시켜 성막하여 제조된 것을 특징으로 한다. In addition, the organic thin film layer is characterized in that it is prepared by coating the ink composition containing the organic compound by a solution process and drying it to form a film.

본 발명의 또 다른 제 18 양태는, 상기 제 17 양태에 따른 유기전기소자를 포함하는 전자기기에 관한 것이다. Another eighteenth aspect of the present invention relates to an electronic device including the organic electric element according to the seventeenth aspect.

본 발명의 일 실시예에 따르면, 유기전기소자용 화합물에 BCB-가교결합성 치환기를 구비함으로써 용해도가 낮은 저분자 유기 화합물의 용해성을 향상시킬 수 있고, 용해성이 증진됨에 따라 생산성이 높은 용액 공정에 적용할 수 있다는 제1효과, 유기화합물에 BCB-가교결합성 치환기를 적어도 2개 이상 구비하는 경우, 비교적 낮은 온도(150℃ 이하)에서 BCB-가교결합성 치환기간의 가교결합으로 안정한 유기박막을 형성할 수 있다는 제2효과, 용액공정을 통해 다층 구조의 유기박막층을 형성하여도 인접한 층이 용액에 의해 용해되는 현상 없이 안정한 다층구조의 소자제작이 가능하다는 제3효과, 유기소자의 대면적화 및 저비용화가 가능하다는 제4효과를 갖는다.According to one embodiment of the present invention, the solubility of low molecular organic compounds having low solubility can be improved by providing a BCB-crosslinking substituent in the compound for an organic electric device, and as the solubility is improved, it is applied to a solution process with high productivity. The first effect is that, when an organic compound is provided with at least two or more BCB-crosslinkable substituents, a stable organic thin film is formed by cross-linking of the BCB-crosslinkable substituents at a relatively low temperature (below 150°C). The second effect that it is possible to manufacture a device with a stable multi-layer structure without the phenomenon of dissolving the adjacent layer by the solution even if a multi-layer organic thin film layer is formed through the solution process, the third effect that the organic device has a large area and low cost It has the fourth effect that anger is possible.

본 발명에 따른 유기화합물은 가교결합이 가능한 BCB 치환기를 구비함으로써 각종 용매에 대한 용해성이 향상될 수 있다. 또한, 종래기술에서 저분자 유기화합물은 용해성이 떨어지는 문제로 인하여 주로 증착공정을 통해 유기박막을 형성하였는데, 본 발명에 따른 유기화합물은 용해성의 향상으로 각종 용액공정에 적합한 특성을 제공할 수 있다. The organic compound according to the present invention may have improved solubility in various solvents by having a BCB substituent capable of crosslinking. In addition, in the prior art, organic thin films were formed mainly through a deposition process due to low solubility of low molecular organic compounds, but the organic compound according to the present invention can provide characteristics suitable for various solution processes by improving solubility.

또한, 종래기술에서는 용액공정을 통해 유기박막을 형성하더라도, 안정한 유기박막을 형성하기 위하여 고온 조건에서 수행하여야 하는 문제점이 있었다. 그러나 본 발명에 따른 유기화합물은 용매에 대한 용해성이 우수할 뿐만 아니라, 화합물에 구비된 BCB 치환기간의 가교결합으로 저온공정으로도 열에 안정한 박막을 형성할 수 있기 때문에 유기소자의 대량생산, 대면적화 및 저비용화를 가능케 할 수 있는 것이다. In addition, in the prior art, even if an organic thin film is formed through a solution process, there is a problem in that it must be performed under high temperature conditions in order to form a stable organic thin film. However, the organic compound according to the present invention not only has excellent solubility in solvents, but also can form a heat-stable thin film even at a low temperature due to crosslinking between BCB substituents provided in the compound, so that mass production and large-area organic devices can be formed. And cost reduction is possible.

본 발명의 효과는 상기한 효과로 한정되는 것은 아니며, 본 발명의 상세한 설명 또는 특허청구범위에 기재된 발명의 구성으로부터 추론 가능한 모든 효과를 포함하는 것으로 이해되어야 한다.The effects of the present invention are not limited to the above effects, and should be understood to include all effects that can be inferred from the detailed description of the present invention or the configuration of the invention described in the claims.

이하에서 본 발명의 구현예를 상세하게 설명하기로 한다. 그러나 본 발명은 여러 가지 상이한 형태로 구현될 수 있으며, 따라서 여기에서 설명하는 실시예로 한정되는 것은 아니다. Hereinafter, embodiments of the present invention will be described in detail. However, the present invention may be embodied in many different forms and, therefore, is not limited to the embodiments described herein.

명세서 전체에서, 어떤 부분이 다른 부분과 "연결(접속, 접촉, 결합)"되어 있다고 할 때, 이는 "직접적으로 연결"되어 있는 경우뿐 아니라, 그 중간에 다른 부재를 사이에 두고 "간접적으로 연결"되어 있는 경우도 포함한다. 또한, 어떤 부분이 어떤 구성요소를 "포함"한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성요소를 더 구비할 수 있다는 것을 의미한다. Throughout the specification, when a part is said to be "connected (connected, contacted, combined)" with another part, this is not only "directly connected", but also "indirectly connected" with another member in between. "Including cases where In addition, when a part "includes" a certain component, it means that it may further include other components without excluding other components unless otherwise stated.

본 명세서에서 사용한 용어는 단지 특정한 실시예를 설명하기 위해 사용된 것으로, 본 발명을 한정하려는 의도가 아니다. 단수의 표현은 문맥상 명백하게 다르게 뜻하지 않는 한, 복수의 표현을 포함한다. 본 명세서에서, "포함하다" 또는 "가지다" 등의 용어는 명세서상에 기재된 특징, 숫자, 단계, 동작, 구성요소, 부품 또는 이들을 조합한 것이 존재함을 지정하려는 것이지, 하나 또는 그 이상의 다른 특징들이나 숫자, 단계, 동작, 구성요소, 부품 또는 이들을 조합한 것들의 존재 또는 부가 가능성을 미리 배제하지 않는 것으로 이해되어야 한다. Terms used in this specification are only used to describe specific embodiments, and are not intended to limit the present invention. Singular expressions include plural expressions unless the context clearly dictates otherwise. In this specification, terms such as "include" or "have" are intended to indicate that there is a feature, number, step, operation, component, part, or combination thereof described in the specification, but one or more other features It should be understood that the presence or addition of numbers, steps, operations, components, parts, or combinations thereof is not precluded.

명세서에서 사용한 용어는 단지 특정한 구현예(태양, 態樣, aspect)(또는 실시예)를 설명하기 위해 사용된 것으로, 본 발명을 한정하려는 의도가 아니다. 단수의 표현은 문맥상 명백하게 다르게 뜻하지 않는 한, 복수의 표현을 포함한다. 본 출원에서, ~포함하다~ 또는 ~이루어진다~ 등의 용어는 명세서 상에 기재된 특징, 숫자, 단계, 동작, 구성요소, 부분품 또는 이들을 조합한 것이 존재함을 지정하려는 것이지, 하나 또는 그 이상의 다른 특징들이나 숫자, 단계, 동작, 구성요소, 부분품 또는 이들을 조합한 것들의 존재 또는 부가 가능성을 미리 배제하지 않는 것으로 이해되어야 한다. 다르게 정의되지 않는 한, 기술적이거나 과학적인 용어를 포함해서 여기서 사용되는 모든 용어들은 본 발명이 속하는 기술 분야에서 통상의 지식을 가진 자에 의해 일반적으로 이해되는 것과 동일한 의미를 가지고 있다. 일반적으로 사용되는 사전에 정의되어 있는 것과 같은 용어들은 관련 기술의 문맥 상 가지는 의미와 일치하는 의미를 가지는 것으로 해석되어야 하며, 본 출원에서 명백하게 정의하지 않는 한, 이상적이거나 과도하게 형식적인 의미로 해석되지 않는다. Terms used in the specification are only used to describe specific embodiments (aspects, configurations, aspects) (or embodiments), and are not intended to limit the present invention. Singular expressions include plural expressions unless the context clearly dictates otherwise. In this application, terms such as ~comprising~ or ~consisting of are intended to designate that there is a feature, number, step, operation, component, part, or combination thereof described in the specification, but one or more other features It should be understood that it does not preclude the possibility of the presence or addition of numbers, steps, operations, components, parts, or combinations thereof. Unless defined otherwise, all terms used herein, including technical or scientific terms, have the same meaning as commonly understood by one of ordinary skill in the art to which the present invention belongs. Terms such as those defined in commonly used dictionaries should be interpreted as having a meaning consistent with the meaning in the context of the related art, and unless explicitly defined in the present application, they should not be interpreted in an ideal or excessively formal meaning. don't

이하, 구조화된 화학식 등을 참조하여 본 발명의 실시예를 구체적으로 설명하기로 한다. Hereinafter, embodiments of the present invention will be described in detail with reference to structured chemical formulas and the like.

가교결합성 BCB-작용화된 물질은 종래의 OLED 적용에서도 발견되어 왔다. 본 발명에서는 벤조시클로부텐 화합물의 고리상에 다양한 작용기(예를 들어, 산소 공여체, 수산기, 아미노기 등)를 치환시키는 것에 의해 개환 온도(temperature of ring opening)를 150℃ 이하, 특히, 120℃ 이하의 저온으로 낮출 수 있고, 이로인해, OLED 적용에서의 용액-공정 조건을 충분히 만족시킬 수 있음을 알았다. 특히, 산소 공여체의 치환은 벤조시클로부텐 화합물의 개환 온도를 100~120℃로 유의미하게 감소시킬 수 있어 유의미한 공정 잇점을 가질 수 있다. Crosslinkable BCB-functionalized materials have also been found in conventional OLED applications. In the present invention, by substituting various functional groups (eg, oxygen donor, hydroxyl group, amino group, etc.) on the ring of the benzocyclobutene compound, the temperature of ring opening is 150 ° C. or less, particularly 120 ° C. or less It was found that it can be lowered to a low temperature, thereby sufficiently satisfying the solution-processing conditions in OLED applications. In particular, substitution of the oxygen donor can significantly reduce the ring-opening temperature of the benzocyclobutene compound to 100 to 120° C., thereby providing significant process advantages.

구체적으로 본 발명은 OLED 적용을 위한 유기박막을 형성하는 코어 물질의 말단에 적어도 2개 이상의 벤조시클로부텐 가교결합성 유도체를 포함하는 유기화합물에 관한 것이다. 특히, 본 발명에 따른 유기화합물은 아래 [구조식 1]로부터 선택된 적어도 하나의 화합물을 포함하는 조성물을 제공한다. Specifically, the present invention relates to an organic compound containing at least two or more benzocyclobutene crosslinkable derivatives at the ends of a core material forming an organic thin film for OLED application. In particular, the organic compound according to the present invention provides a composition comprising at least one compound selected from [Structural Formula 1] below.

[구조식 1][Structural Formula 1]

Figure 112020131688418-pat00018
Figure 112020131688418-pat00018

상기 [구조식 1]에서, R1, R2는 서로 같거나 상이하고, 각각 독립적으로 수소, 알킬기(alkyl group), 치환된 알킬기(alkyl group), 헤테로사이클로기(heterocyclic group), 치환된 헤테로사이클로기(heterocyclic group), 아릴기(aryl group), 치환된 아릴기(aryl group), 아민기(amine group), 피리딘기(pyridine group), 피리미딘기(pyrimidine group), 트이라졸기(triazole group), 트리아진기(triazine group), 포스파인기(phosphine group), 시릴기(silole group), 아릴아민기(arylamine), 카바졸기(carbazole) 또는 치환된 카바졸기로부터 선택되고; In [Formula 1], R 1 and R 2 are the same as or different from each other, and each independently represents hydrogen, an alkyl group, a substituted alkyl group, a heterocyclic group, or a substituted heterocycle. Heterocyclic group, aryl group, substituted aryl group, amine group, pyridine group, pyrimidine group, triazole group ), a triazine group, a phosphine group, a silole group, an arylamine group, a carbazole group, or a substituted carbazole group;

상기 X1, X2는 서로 같거나 상이하고, 각각 독립적으로 알킬기(alkyl group), 치환된 알킬기(alkyl group), 헤테로사이클로기(heterocyclic group), 치환된 헤테로사이클로기(heterocyclic group)로부터 선택될 수 있고; The X 1 and X 2 are the same as or different from each other, and each independently selected from an alkyl group, a substituted alkyl group, a heterocyclic group, and a substituted heterocyclic group. can;

상기 R1, R2, X1, X2중 선택된 적어도 1곳 이상에는 아래 [구조식 2]의 벤조시클로부텐기(benzocyclobutene)가 직접 적용되거나 수소, 알킬기(alkyl group), 치환된 알킬기(alkyl group), 헤테로사이클로기(heterocyclic group), 치환된 헤테로사이클로기(heterocyclic group), 아릴기(aryl group), 치환된 아릴기(aryl group), 아민기(amine group)에 아래 [구조식 2]의 벤조시클로부텐기(benzocyclobutene)로 치환된 유도체가 적용되며;At least one selected from among R 1 , R 2 , X 1 , and X 2 , a benzocyclobutene group of [Formula 2] below is directly applied, or hydrogen, an alkyl group, or a substituted alkyl group ), a heterocyclic group, a substituted heterocyclic group, an aryl group, a substituted aryl group, and an amine group in [Formula 2] below A derivative substituted with a cyclobutene group (benzocyclobutene) is applied;

[구조식 2][Structural Formula 2]

Figure 112020131688418-pat00019
Figure 112020131688418-pat00019

상기 [구조식 2]에서, Y는 수소 또는 탄화수소, 특히, C1~C13의 탄소 체인을 가진 알킬기 또는 치환된 알칼기, 수소, 아민 또는 할로겐을 가지고 있는 알킬기이고, X1, X2, X3, X4, X5는 서로 같거나 상이하고, 각각 독립적으로 수소, 탄화수소, 치환된 탄화수소, 할로겐, 시아노, 니트로, 하이드록실, 알콕시, 아민 또는 치환된 아민, 카보닐로부터 선택된다. In [Formula 2], Y is hydrogen or hydrocarbon, in particular, an alkyl group having a carbon chain of C 1 to C 13 or a substituted alkyl group, hydrogen, an amine or an alkyl group having a halogen, X 1 , X 2 , X 3 , X 4 , and X 5 are the same as or different from each other, and are each independently selected from hydrogen, hydrocarbon, substituted hydrocarbon, halogen, cyano, nitro, hydroxyl, alkoxy, amine or substituted amine, and carbonyl.

본 발명에서 적용 가능한 상기 헤테로사이클로기(heterocyclic group)의 예로는 테트라히드로푸란(tetrahyrofuran), 싸이오펜(thiophene), 피리딘(pyridine), 피리미딘(pyrimidine), 벤조싸이오펜(benzothiophene), 벤조푸란(benzofuran), 디벤조푸란(dibenzofuran) 등을 포함한다.Examples of the heterocyclic group applicable in the present invention include tetrahyrofuran, thiophene, pyridine, pyrimidine, benzothiophene, benzofuran ( benzofuran), dibenzofuran, and the like.

또한, 본 발명에서 적용 가능한 상기 아릴기(aryl group)의 예로는 페닐(phenyl), 나프틸(naphthyl), 페난트릴(phenanthryl), 피렌일(pyrenyl), 플루오렌일(fluorenyl), 카바조일(cabazolyl), 스피로바이플루오렌(spirobifluorene), 테트라페닐실란(traphenylsilane), 테트라페닐메탄(tetraphenylmethane) 등을 포함한다. In addition, examples of the aryl group applicable in the present invention include phenyl, naphthyl, phenanthryl, pyrenyl, fluorenyl, carbazoyl ( cabazolyl), spirobifluorene, tetraphenylsilane, tetraphenylmethane, and the like.

또한, 본 발명에서 적용 가능한 아민기(amine group)의 예로는 디페닐아민(diphenylamine), 트리페닐아민(triphenylamine) 등을 포함한다.In addition, examples of the amine group applicable in the present invention include diphenylamine, triphenylamine, and the like.

본 발명에 따른 상기 [구조식 1]로 표현되는 유기화합물은 유기전기소자의 제1전극과 제2전극 사이에 배치되는 각종 유기박막을 형성하기 위한 발광층(EML)물질, 정공주입층(HIL) 물질, 정공수송층(HTL) 물질, 전자주입층(EIL) 물질, 전자수송층(ETL) 물질, 전자차단층(EBL) 물질 및 정공차단층(HBL) 물질 등에 다각적으로 사용될 수 있다. The organic compound represented by [Structural Formula 1] according to the present invention is a light emitting layer (EML) material and a hole injection layer (HIL) material for forming various organic thin films disposed between the first electrode and the second electrode of an organic electric device. , a hole transport layer (HTL) material, an electron injection layer (EIL) material, an electron transport layer (ETL) material, an electron blocking layer (EBL) material, and a hole blocking layer (HBL) material.

본 발명에 따른 유기화합물은 120℃ 정도의 낮은 온도에서 가열되는 것에 의해 상기 [구조식 2]의 벤조시클로부텐기(benzocyclobutene group)간에 열이성질체화(thermal isomerization) 반응을 통해 가교 결합을 발생시킨다. When the organic compound according to the present invention is heated at a low temperature of about 120° C., cross-linking occurs between the benzocyclobutene groups of [Structural Formula 2] through a thermal isomerization reaction.

이로 인해, 본 발명에 따른 유기화합물로 이루어진 유기박막의 경우 인접한 유기박막층의 유기용매에 용해되지 않기 때문에 용액공정을 통해 다층의 박막을 적층하더라도 박막이 손상되지 않아 대면적의 다층 구조의 유기전기소자를 제작하는데 최적화된다. For this reason, in the case of the organic thin film made of the organic compound according to the present invention, since it is not dissolved in the organic solvent of the adjacent organic thin film layer, the thin film is not damaged even when multi-layered thin films are stacked through the solution process. is optimized for making

본 발명의 일 구현예에서, 상기 [구조식 1]로 표현되는 본 발명의 유기화합물의 구체적인 예를 들면, 아래의 [화학식 1] 내지 [화학식 14]로부터 선택될 수 있다. In one embodiment of the present invention, specific examples of the organic compound of the present invention represented by [Structural Formula 1] may be selected from [Formula 1] to [Formula 14] below.

Figure 112020131688418-pat00020
Figure 112020131688418-pat00020

Figure 112020131688418-pat00021
Figure 112020131688418-pat00021

Figure 112020131688418-pat00022
Figure 112020131688418-pat00022

Figure 112020131688418-pat00023
Figure 112020131688418-pat00023

Figure 112020131688418-pat00024
Figure 112020131688418-pat00024

Figure 112020131688418-pat00025
Figure 112020131688418-pat00025

Figure 112020131688418-pat00026
Figure 112020131688418-pat00026

Figure 112020131688418-pat00027
Figure 112020131688418-pat00027

Figure 112020131688418-pat00028
Figure 112020131688418-pat00028

Figure 112020131688418-pat00029
Figure 112020131688418-pat00029

Figure 112020131688418-pat00030
Figure 112020131688418-pat00030

Figure 112020131688418-pat00031
Figure 112020131688418-pat00031

Figure 112020131688418-pat00032
Figure 112020131688418-pat00032

Figure 112020131688418-pat00033
Figure 112020131688418-pat00033

본 발명의 다른 구현예에서, 본 발명에 따른 상기 [구조식 1]에 따른 유기화합물, 특히, 상기 [화학식 1] 내지 [화학식 14]의 유기화합물을 포함하는 잉크 조성물을 제공한다.In another embodiment of the present invention, an ink composition comprising an organic compound according to [Structural Formula 1], in particular, an organic compound represented by [Formula 1] to [Formula 14] according to the present invention is provided.

상기 잉크 조성물은 용매를 포함하는 용액 또는 현탁액일 수 있고, 상기 용매는, 예를 들어, 아니솔, 디메틸 아니솔, 크실렌, o-크실렌, m-크실렌, p-크실렌, 톨루엔, 메시틸렌, 메틸 벤조에이트, 다이옥산, 테트라하이드로 퓨란, 메틸 테트라하이드로퓨란, 테트라하이드로 피란, 테트랄린, 베라트롤, 클로로벤젠, N-메틸 피롤리돈, N,N-디메틸포름아마이드, 디메틸술폭사이드 및 이들의 조합으로 이루어진 군으로부터 선택된 하나를 포함할 수 있다. The ink composition may be a solution or suspension containing a solvent, and the solvent is, for example, anisole, dimethyl anisole, xylene, o-xylene, m-xylene, p-xylene, toluene, mesitylene, methyl Benzoate, dioxane, tetrahydrofuran, methyl tetrahydrofuran, tetrahydropyran, tetralin, veratrol, chlorobenzene, N-methyl pyrrolidone, N,N-dimethylformamide, dimethylsulfoxide and combinations thereof It may include one selected from the group consisting of.

상기 잉크 조성물을 도포한 뒤 용매를 제거하여 성막함으로써 유기 박막층을 형성할 수 있다. 상기 잉크 조성물은 안료 또는 염료를 더 포함할 수 있다. 상기 잉크 조성물은 인광 도펀트 또는 형광 도펀트를 더 포함할 수도 있다. An organic thin film layer may be formed by applying the ink composition and then removing the solvent to form a film. The ink composition may further include a pigment or dye. The ink composition may further include a phosphorescent dopant or a fluorescent dopant.

본 발명의 또 다른 구현예에서, 음극과 양극 사이에 적어도 발광층을 포함하는 일층 또는 복수층으로 이루어지는 유기 박막층이 다층으로 적층되어 있는 유기전기소자에 있어서, 상기 유기 박막층 중 적어도 1층이 상기 [구조식 1]에 따른 유기화합물, 특히, 상기 [화학식 1] 내지 [화학식 14]의 유기화합물을 함유하는 것을 특징으로 하는 유기전기소자를 제공한다. 특히, 상기 유기전기소자는 유기전계발광소자(OLED)인 것이 바람직하다. In another embodiment of the present invention, in an organic electric device in which a plurality of organic thin film layers including one or a plurality of layers including at least a light emitting layer are stacked between a cathode and an anode, at least one of the organic thin film layers has the [structural formula 1], in particular, an organic electric device characterized in that it contains the organic compound of [Chemical Formula 1] to [Chemical Formula 14]. In particular, the organic electric device is preferably an organic light emitting device (OLED).

상기 유기 박막층은 본 발명에 따른 유기화합물을 포함하는 상술한 잉크 조성물을 이용하여 용액공정으로 성막하여 제조될 수 있다. 이러한 용액 공정은 스핀코팅, 그라비아 옵셋 인쇄, 리버스 옵셋 인쇄, 스크린 인쇄, 롤투롤 인쇄, 슬롯다이코팅, 침지코팅, 스프레이코팅, 닥터블레이드 코팅, 잉크젯 코팅으로 이루어지는 군으로부터 선택되는 어느 하나의 방법을 포함한다. The organic thin film layer may be prepared by forming a film through a solution process using the above-described ink composition containing the organic compound according to the present invention. The solution process includes any one method selected from the group consisting of spin coating, gravure offset printing, reverse offset printing, screen printing, roll-to-roll printing, slot die coating, dip coating, spray coating, doctor blade coating, and inkjet coating. do.

상기 유기 박막층은 상기 유기화합물이 발광층 물질, 정공주입층 물질, 정공수송층 물질, 전자주입층 물질, 전자수송층 물질, 전자차단층 물질 및 정공차단층 물질로 이루어진 군으로부터 선택된 적어도 하나를 포함하여 형성된 층을 포함할 수 있다. 상기 발광층 물질은 인광 또는 형광 호스트 및 인광 도펀트 또는 형광 도펀트 물질일 수 있다. The organic thin film layer is a layer formed of the organic compound including at least one selected from the group consisting of a light emitting layer material, a hole injection layer material, a hole transport layer material, an electron injection layer material, an electron transport layer material, an electron blocking layer material, and a hole blocking layer material. can include The emission layer material may be a phosphorescent or fluorescent host and a phosphorescent dopant or fluorescent dopant material.

특히, 상기 유기전계발광소자(OLED)는 양극, 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 및 음극이 이 순서대로 적층된 구조를 가질 수 있다. 상기 발광층은 본 발명에 따른 유기화합물과 함께, 적색, 녹색, 청색 또는 백색을 포함하는 인광 도펀트 또는 형광 도펀트를 포함할 수 있다. 예를 들어, 상기 인광 도펀트는 Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb 및 Tm으로 이루어진 군으로부터 선택된 하나 이상의 원소를 포함하는 유기금속화합물일 수 있다. In particular, the organic light emitting device (OLED) may have a structure in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode are stacked in this order. The light emitting layer may include a phosphorescent dopant or a fluorescent dopant including red, green, blue or white, together with the organic compound according to the present invention. For example, the phosphorescent dopant may be an organometallic compound including one or more elements selected from the group consisting of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, and Tm.

상기 정공수송층, 정공주입층, 정공차단층, 전자주입수송층, 전자수송층, 전자주입층 및 전자차단층은 전술한 본 발명에 따른 유기화합물을 포함할 수 있다. The hole transport layer, the hole injection layer, the hole blocking layer, the electron injection transport layer, the electron transport layer, the electron injection layer, and the electron blocking layer may include the above-described organic compound according to the present invention.

이하에서, 본 발명에 따른 유기전기소자로서 유기전계발광소자에 대하여 예를들어 설명한다. 본 발명의 유기전계발광소자는 양극(정공주입전극), 정공주입층(HIL) 및/또는 정공수송층(HTL), 발광층(EML) 및 음극(전자주입전극)이 순차적으로 적층된 구조를 가질 수 있으며, 바람직하게는, 양극과 발광층 사이에 전자차단층(EBL)을, 그리고 음극과 발광층 사이에 전자수송층(ETL), 전자주입층(EIL) 또는 정공차단층(HBL)을 추가로 포함할 수 있다. Hereinafter, an organic electroluminescent device as an organic electric device according to the present invention will be described as an example. The organic light emitting device of the present invention may have a structure in which an anode (hole injection electrode), a hole injection layer (HIL) and/or a hole transport layer (HTL), a light emitting layer (EML), and a cathode (electron injection electrode) are sequentially stacked. Preferably, an electron blocking layer (EBL) may be further included between the anode and the light emitting layer, and an electron transport layer (ETL), an electron injection layer (EIL) or a hole blocking layer (HBL) may be further included between the cathode and the light emitting layer. have.

본 발명에 따른 유기전계발광소자의 제조방법으로는, 먼저 기판 표면에 양극용 물질을 통상적인 방법으로 코팅하여 양극을 형성한다. 이때, 사용되는 기판은 투명성, 표면 평활성, 취급 용이성 및 방수성이 우수한 유리기판 또는 투명 플라스틱 기판이 바람직하다. 또한, 양극용 물질로는 투명하고 전도성이 우수한 산화인듐주석(ITO), 산화인듐아연(IZO), 산화주석(SnO2), 산화아연(ZnO) 등이 사용될 수 있다. In the manufacturing method of the organic light emitting device according to the present invention, first, an anode is formed by coating a substrate surface with a material for an anode in a conventional manner. At this time, the substrate used is preferably a glass substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and water resistance. In addition, as the material for the anode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity, may be used.

다음으로, 상기 양극 표면에 정공주입층(HIL) 물질을 스핀 코팅하여 정공주입층을 형성하고, 상기 정공주입층 표면에 정공수송층(HTL) 물질을 스핀 코팅하여 정공수송층을 형성하고, 상기 정공수송층 표면에 발광층(EML) 물질을 스핀 코팅하여 발광층을 형성하고, 상기 발광층 표면에 전자수송층(ETL) 물질을 스핀 코팅하여 전자수송층을 형성한다. Next, a hole injection layer (HIL) material is spin-coated on the surface of the anode to form a hole injection layer, and a hole transport layer (HTL) material is spin-coated on the surface of the hole injection layer to form a hole transport layer. A light emitting layer (EML) material is spin-coated on the surface to form the light emitting layer, and an electron transport layer is formed by spin coating an electron transport layer (ETL) material on the surface of the light emitting layer.

이때, 선택적으로는, 발광층과 전자수송층 사이에 정공차단층(HBL)을 추가로 형성하고 발광층에 인광 도펀트를 함께 사용함으로써, 삼중항 여기자 또는 정공이 전자수송층으로 확산되는 현상을 방지할 수 있다. 정공차단층의 형성은 정공차단층 물질을 스핀 코팅하여 실시할 수 있으며, 정공차단층 물질의 경우 본 발명의 유기화합물이 사용될 수 있다. At this time, it is possible to selectively prevent diffusion of triplet excitons or holes into the electron transport layer by additionally forming a hole blocking layer (HBL) between the light emitting layer and the electron transport layer and using a phosphorescent dopant in the light emitting layer together. Formation of the hole blocking layer may be performed by spin-coating the hole blocking layer material, and in the case of the hole blocking layer material, the organic compound of the present invention may be used.

상기 전자수송층 표면에 전자주입층(EIL) 물질을 스핀 코팅하여 전자주입층을 형성한다. 마지막으로, 상기 전자주입층 표면에 음극용 물질을 통상적인 방법으로 진공 열증착하여 음극을 형성한다. 이때, 사용되는 음극용 물질로는 리튬(Li), 알루미늄(Al), 알루미늄-리튬(Al-Li), 칼슘(Ca), 마그네슘(Mg), 마그네슘-인듐(Mg-In), 마그네슘-은(Mg-Ag) 등이 사용될 수 있다. 또한, 전면발광 유기전계발광소자의 경우 산화인듐주석(ITO) 또는 산화인듐아연(IZO)를 사용하여 빛이 투과할 수 있는 투명한 음극을 형성할 수도 있다. An electron injection layer is formed by spin-coating an electron injection layer (EIL) material on the surface of the electron transport layer. Finally, a negative electrode is formed by vacuum thermal evaporation of a negative electrode material on the surface of the electron injection layer in a conventional manner. At this time, the negative electrode material used is lithium (Li), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and the like may be used. In addition, in the case of a top-emitting organic light emitting device, a transparent cathode through which light can pass may be formed using indium tin oxide (ITO) or indium zinc oxide (IZO).

본 발명에 따른 유기 전계발광소자는 상술한 바와 같은 순서, 즉 양극/정공주입층/정공수송층/발광층/정공차단층/전자수송층/전자주입층/음극 순으로 제조하여도 되고, 그 반대로 음극/전자주입층/전자수송층/정공차단층/발광층/정공수송층/정공주입층/양극의 순서로 제조하여도 무방하다. The organic electroluminescent device according to the present invention may be manufactured in the order described above, that is, in the order of anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode, or vice versa, cathode/hole injection layer/cathode. It may be prepared in the order of electron injection layer/electron transport layer/hole blocking layer/light emitting layer/hole transport layer/hole injection layer/anode.

본 발명의 또 다른 구현예에서, 상기 유기전계발광소자를 포함하는 전자기기(또는 전자장치)를 제공한다. In another embodiment of the present invention, an electronic device (or electronic device) including the organic light emitting device is provided.

이하에서, 본 발명에 따른 유기화합물들의 합성방법을 대표적인 예를 통해서 아래에서 설명한다. 그러나, 본 발명의 유기화합물들의 합성방법이 하기 예시된 방법으로 한정되는 것은 아니며, 본 발명의 유기화합물들은 하기에 예시된 방법과 이 분야의 공지의 방법에 의해 제조될 수 있다.Hereinafter, a method for synthesizing organic compounds according to the present invention will be described below through representative examples. However, the synthesis method of the organic compounds of the present invention is not limited to the methods exemplified below, and the organic compounds of the present invention may be prepared by the methods exemplified below and methods known in the art.

<중간체 합성<Synthesis of intermediates >>

아래와 같은 과정을 통해서 본 발명에 따른 유기화합물을 제조하기 위한 중간체들을 합성하였다. Intermediates for preparing the organic compound according to the present invention were synthesized through the following process.

(1) 중간체(a)(1) Intermediate (a)

Figure 112020131688418-pat00034
Figure 112020131688418-pat00034

상기 반응식을 참조하면, cesium fluoride(11.4g, 75.0mmol)를 둥근 플라스크에 넣고 건조시킨다. 둥근 플라스크에 100mL의 acetonitrile을 넣은 후에 butyl vinyl ether(4.9mL, 38mmol)와 4-bromo-2-(trimethylsilyl)phenyl trifluoromethanesulfonate(5.70g, 15.7mmol)를 천천히 적가한다. 24시간 동안 실온에서 반응시킨 후 물과 DCM을 넣고 유기층을 분리한다. 컬럼 크로마토그래피 (PE:DCM =1:8)로 정제하여 아래의 중간체(a)를 얻는다.Referring to the above reaction scheme, cesium fluoride (11.4 g, 75.0 mmol) was put into a round flask and dried. After putting 100mL of acetonitrile in a round flask, slowly add butyl vinyl ether (4.9mL, 38mmol) and 4-bromo-2-(trimethylsilyl)phenyl trifluoromethanesulfonate (5.70g, 15.7mmol) dropwise. After reacting at room temperature for 24 hours, water and DCM were added to separate the organic layer. Purification by column chromatography (PE:DCM = 1:8) yields the intermediate (a) below.

중간체(a)Intermediate (a)

Figure 112020131688418-pat00035
Figure 112020131688418-pat00035

(2) 중간체(b) (2) Intermediate (b)

Figure 112020131688418-pat00036
Figure 112020131688418-pat00036

상기 반응식을 참조하면, 플라스크에 상기 중간체(a)(1g, 4mmol), Bis(pinacolato)diboron(1.1g, 4.2mmol), Pd(dppf)Cl2(0.7g, 0.06mmol)와 Potassium acetate(0.78g, 8mmol)를 넣고, 50mL의 DMF로 녹인 후, 질소를 충분히 흘려준다. 그 후에 90℃에서 환류시킨다. 반응 종료 후 물과 MC로 추출해준다. MgSO4로 잔여 수분을 제거한 후에 methylene chloride:hexane을 사용하여 관크로마토그래피로 정제하여 아래의 중간체(b)를 얻는다.Referring to the reaction scheme, the intermediate (a) (1g, 4mmol), Bis(pinacolato)diboron (1.1g, 4.2mmol), Pd(dppf)Cl 2 (0.7g, 0.06mmol) and Potassium acetate (0.78mmol) were placed in a flask. g, 8 mmol), dissolved in 50 mL of DMF, and then sufficiently flowed with nitrogen. It is then refluxed at 90°C. After completion of the reaction, it was extracted with water and MC. After removing residual moisture with MgSO 4 , methylene chloride:hexane was used to purify the mixture by column chromatography to obtain the intermediate (b) below.

중간체(b)Intermediate (b)

Figure 112020131688418-pat00037
Figure 112020131688418-pat00037

(3) 중간체(c)(3) Intermediate (c)

Figure 112020131688418-pat00038
Figure 112020131688418-pat00038

상기 반응식을 참조하면, 질소 분위기 하에서 500mL two-neck 플라스크에, 1,3,5-tribromobenzene(0.63g, 2mmol), 상기 중간체(b)(1.2g, 4mmol), Pd(PPh3)4 (0.2g, 0.0002mol)를 넣고, THF(100mL)를 넣어 교반시킨다. 플라스크 안에 물질이 모두 녹으면 potassium carbonate solution(2N, 100mL)를 넣는다. 80℃에서 12시 간 동안 환류시켜 반응을 진행한다. 반응 종료 후, 상온에서 식히고 ethyl acetate/증류수로 추출하여 유기층을 분리한다. 분리한 유기층의 용매를 모두 날린 후, 컬럼크로마토그래피로 정제하여 아래의 중간체(c)를 얻는다.Referring to the reaction scheme, in a 500mL two-neck flask under a nitrogen atmosphere, 1,3,5-tribromobenzene (0.63g, 2mmol), the intermediate (b) (1.2g, 4mmol), Pd (PPh 3 ) 4 (0.2 g, 0.0002 mol) was added, and THF (100 mL) was added and stirred. When all substances in the flask are dissolved, add potassium carbonate solution (2N, 100mL). The reaction proceeds by refluxing at 80 ° C. for 12 hours. After completion of the reaction, the mixture was cooled at room temperature and extracted with ethyl acetate/distilled water to separate an organic layer. After removing all the solvent from the separated organic layer, it is purified by column chromatography to obtain the intermediate (c) below.

중간체(c)Intermediate (c)

Figure 112020131688418-pat00039
Figure 112020131688418-pat00039

(4) 중간체(d) (4) Intermediate (d)

Figure 112020131688418-pat00040
Figure 112020131688418-pat00040

상기 반응식을 참조하면, 질소 분위기 하에서 500mL two-neck 플라스크에, 2,6-dibromonaphthalene(1.14g, 4mmol), 상기 중간체(b)(1.2g, 4mmol), Pd(PPh3)4 (0.2g, 0.0002mol)를 넣고, THF(100mL)를 넣어 교반시킨다. 플라스크 안에 물질이 모두 녹으면 potassium carbonate solution(2N, 100mL)를 넣는다. 80℃에서 12시 간 동안 환류시켜 반응을 진행한다. 반응 종료 후, 상온에서 식히고 ethyl acetate/증류수로 추출하여 유기층을 분리한다. 분리한 유기층의 용매를 모두 날린 후, 컬럼크로마토그래피로 정제하여 아래의 중간체(d)를 얻는다.Referring to the reaction scheme, in a 500mL two-neck flask under a nitrogen atmosphere, 2,6-dibromonaphthalene (1.14g, 4mmol), the intermediate (b) (1.2g, 4mmol), Pd (PPh 3 ) 4 (0.2g, 0.0002 mol) was added, and THF (100 mL) was added and stirred. When all substances in the flask are dissolved, add potassium carbonate solution (2N, 100mL). The reaction proceeds by refluxing at 80 ° C. for 12 hours. After completion of the reaction, the mixture was cooled at room temperature and extracted with ethyl acetate/distilled water to separate an organic layer. After removing all the solvent of the separated organic layer, it is purified by column chromatography to obtain the intermediate (d) below.

중간체(d)Intermediate (d)

Figure 112020131688418-pat00041
Figure 112020131688418-pat00041

(5) 중간체(e)(5) Intermediate (e)

Figure 112020131688418-pat00042
Figure 112020131688418-pat00042

상기 반응식을 참조하면, 질소 분위기 하에서 500mL two-neck 플라스크에, 상기 중간체(c)(1.0g, 0.002mol), 9,10-Bis(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)anthracene(0.86g, 0.002mol), Pd(PPh3)4 (0.2g, 0.0002mol)를 넣고, THF(100mL)를 넣어 교반시킨다. 플라스크 안에 물질이 모두 녹으면 potassium carbonate solution(2N, 100mL)를 넣는다. 80℃에서 12시간 환류시켜 반응을 진행한다. 반응 종료 후, 상온에서 식히고 EA/증류수로 추출하여 유기층을 분리한다. 분리한 유기층의 용매를 모두 날린 후, 컬럼크로마토그래피로 정제하여 아래의 중간체(e)를 얻는다.Referring to the reaction equation, in a 500mL two-neck flask under a nitrogen atmosphere, the intermediate (c) (1.0g, 0.002mol), 9,10-Bis (4,4,5,5-tetramethyl[1.3.2]dioxaborolan After adding -2-yl)anthracene (0.86g, 0.002mol) and Pd(PPh 3 ) 4 (0.2g, 0.0002mol), add THF (100mL) and stir. When all substances in the flask are dissolved, add potassium carbonate solution (2N, 100mL). The reaction proceeds by refluxing at 80 ° C. for 12 hours. After completion of the reaction, the mixture was cooled at room temperature and extracted with EA/distilled water to separate an organic layer. After removing all the solvent from the separated organic layer, it is purified by column chromatography to obtain the intermediate (e) below.

중간체(e)intermediate (e)

Figure 112020131688418-pat00043
Figure 112020131688418-pat00043

(6) 중간체(f)(6) Intermediate (f)

Figure 112020131688418-pat00044
Figure 112020131688418-pat00044

상기 반응식을 참조하면, 질소 분위기 하에서 500mL two-neck 플라스크에, 3,7-dibromodibenzo[b,d]furan(1.3g, 4mmol), 상기 중간체(b)(1.2g, 4mmol), Pd(PPh3)4(0.2g, 0.0002mol)를 넣고, THF(100mL)를 넣어 교반시킨다. 플라스크 안에 물질이 모두 녹으면 potassium carbonate solution(2N, 100mL)를 넣는다. 80℃에서 12시간 동안 환류시켜 반응을 진행한다. 반응 종료 후, 상온에서 식히고 ethyl acetate/증류수로 추출하여 유기층을 분리한다. 분리한 유기층의 용매를 모두 날린 후, 컬럼크로마토그래피로 정제하여 아래의 중간체 (f)를 얻는다.Referring to the reaction scheme, in a 500mL two-neck flask under a nitrogen atmosphere, 3,7-dibromodibenzo[b,d]furan (1.3g, 4mmol), the intermediate (b) (1.2g, 4mmol), Pd (PPh 3 ) 4 (0.2g, 0.0002mol) was added, and THF (100mL) was added and stirred. When all substances in the flask are dissolved, add potassium carbonate solution (2N, 100mL). The reaction proceeds by refluxing at 80 ° C. for 12 hours. After completion of the reaction, the mixture was cooled at room temperature and extracted with ethyl acetate/distilled water to separate an organic layer. After removing all the solvent from the separated organic layer, it is purified by column chromatography to obtain the intermediate (f) below.

중간체(f)intermediate (f)

Figure 112020131688418-pat00045
Figure 112020131688418-pat00045

(7) 중간체(g)(7) Intermediate (g)

Figure 112020131688418-pat00046
Figure 112020131688418-pat00046

상기 반응식을 참조하면, 질소 분위기 하에서 500mL two-neck 플라스크에, N-(4-bromophenyl)-7-butoxy-N-(7-butoxybicyclo[4.2.0]octa-1(6),2,4-trien-3-yl)bicyclo[4.2.0]octa-1(6),2,4-trien-3-amine(1.04g, 0.002mol), 9,10-Bis(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)anthracene(0.86g, 0.002mol), Pd(PPh3)4(0.2g, 0.0002mol)를 넣고, THF(100mL)를 넣어 교반시킨다. 플라스크 안에 물질이 모두 녹으면 potassium carbonate solution (2N, 100 mL)를 넣는다. 80℃에서 12시간 환류시켜 반응을 진행한다. 반응 종료 후, 상온에서 식히고 EA/증류수로 추출하여 유기층을 분리한다. 분리한 유기층의 용매를 모두 날린 후, 컬럼크로마토그래피로 정제하여 아래의 중간체 (g)를 얻었다Referring to the above reaction formula, in a 500mL two-neck flask under a nitrogen atmosphere, N-(4-bromophenyl)-7-butoxy-N-(7-butoxybicyclo[4.2.0]octa-1(6),2,4- trien-3-yl)bicyclo[4.2.0]octa-1(6),2,4-trien-3-amine(1.04g, 0.002mol), 9,10-Bis(4,4,5,5- After adding tetramethyl[1.3.2]dioxaborolan-2-yl)anthracene (0.86g, 0.002mol) and Pd(PPh 3 ) 4 (0.2g, 0.0002mol), add THF (100mL) and stir. When all substances in the flask are dissolved, add potassium carbonate solution (2N, 100 mL). The reaction proceeds by refluxing at 80 ° C. for 12 hours. After completion of the reaction, the mixture was cooled at room temperature and extracted with EA/distilled water to separate an organic layer. After removing all the solvent from the separated organic layer, it was purified by column chromatography to obtain the intermediate (g) below.

중간체(g)Intermediate (g)

Figure 112020131688418-pat00047
Figure 112020131688418-pat00047

(8) 중간체(h)(8) Intermediate (h)

Figure 112020131688418-pat00048
Figure 112020131688418-pat00048

상기 반응식을 참조하면, cesium fluoride(11.4g, 75.0mmol)를 둥근 플라스크에 넣고 건조시킨다. 둥근 플라스크에 100mL의 acetonitrile을 넣은 후에 (2-bromoethoxy)ethene(4.1mL, 38mmol)와 2-(trimethylsilyl)phenyl trifluoromethanesulfonate(4.8g, 15.7mmol)를 천천히 적가한다. 24시간 동안 실온에서 반응시킨 후 물과 DCM을 넣고 유기층을 분리한다. 컬럼 크로마토그래피로 정제하여 아래의 중간체 (h)를 얻는다.Referring to the above reaction scheme, cesium fluoride (11.4 g, 75.0 mmol) was put into a round flask and dried. After putting 100mL of acetonitrile in a round flask, slowly add (2-bromoethoxy)ethene (4.1mL, 38mmol) and 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (4.8g, 15.7mmol) dropwise. After reacting at room temperature for 24 hours, water and DCM were added to separate the organic layer. It is purified by column chromatography to obtain the intermediate (h) below.

중간체 (h) intermediate (h)

Figure 112020131688418-pat00049
Figure 112020131688418-pat00049

(9) 중간체(i) (9) Intermediate (i)

Figure 112020131688418-pat00050
Figure 112020131688418-pat00050

상기 반응식을 참조하면, 질소 분위기 하에서 500mL two-neck 플라스크에bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)amine(0.84g, 0.002mol), 상기 중간체 (h)(0.91g, 0.004mol), Pd(PPh3)4(0.2g, 0.0002mol)를 넣고, THF(100mL)를 넣어 교반시킨다. 플라스크 안에 물질이 모두 녹으면 potassium carbonate solution(2N, 100 mL)를 넣는다. 80℃에서 12시간 환류시켜 반응을 진행한다. 반응 종료 후, 상온에서 식히고 EA/증류수로 추출하여 유기층을 분리한다. 분리한 유기층의 용매를 모두 날린 후, 컬럼크로마토그래피로 정제하여 상기 중간체 (i)를 얻었다.Referring to the above reaction scheme, bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)amine (0.84g, 0.002 mol), the intermediate (h) (0.91 g, 0.004 mol), Pd(PPh 3 ) 4 (0.2 g, 0.0002 mol) were added, and THF (100 mL) was added and stirred. When all substances in the flask are dissolved, add potassium carbonate solution (2N, 100 mL). The reaction proceeds by refluxing at 80 ° C. for 12 hours. After completion of the reaction, the mixture was cooled at room temperature and extracted with EA/distilled water to separate an organic layer. After removing all the solvent from the separated organic layer, it was purified by column chromatography to obtain the intermediate (i).

중간체(i)Intermediate (i)

Figure 112020131688418-pat00051
Figure 112020131688418-pat00051

(10) 중간체(j) (10) Intermediate (j)

Figure 112020131688418-pat00052
Figure 112020131688418-pat00052

상기 반응식을 참조하면, 상기 중간체(i)(2.3g, 5mmol), P(t-Bu)3(0.04g, 0.22mmol), Pd2(dba)3(0.11g, 0.12mmol), 1,4-dibromobenzene(0.58g, 2.5mmol), 그리고 tert-butoxide(1.0g, 10.6mmol)을 toluene(30mL)에 용해시킨다. 100℃에서 20시간동안 반응시킨다. 반응 종료 후, 실온에서 냉각시킨다. 냉각된 혼합물을 dichloromethane으로 추출한 후에 MgSO4로 건조시킨다. 컬럼 크로마토그래피로 정제하여 아래의 중간체 (j)를 얻는다.Referring to the reaction scheme, the intermediate (i) (2.3g, 5mmol), P(t-Bu) 3 (0.04g, 0.22mmol), Pd 2 (dba) 3 (0.11g, 0.12mmol), 1,4 Dissolve -dibromobenzene (0.58 g, 2.5 mmol) and tert-butoxide (1.0 g, 10.6 mmol) in toluene (30 mL). React for 20 hours at 100 ℃. After completion of the reaction, it is cooled at room temperature. The cooled mixture was extracted with dichloromethane and dried with MgSO 4 . Purification by column chromatography gives the intermediate (j) below.

중간체(j)Intermediate (j)

Figure 112020131688418-pat00053
Figure 112020131688418-pat00053

(11) 중간체(k) (11) Intermediate (k)

Figure 112020131688418-pat00054
Figure 112020131688418-pat00054

상기 반응식을 참조하면, 질소 분위기 하에서 500mL two-neck 플라스크에, t상기 중간체(j)(1.23g, 0.002mol), 9,10-Bis(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)anthracene(0.86g, 0.002mol), Pd(PPh3)4 (0.2g, 0.0002mol)를 넣고, THF(100mL)를 넣어 교반시킨다. 플라스크 안에 물질이 모두 녹으면 potassium carbonate solution(2N, 100 mL)을 넣는다. 80℃에서 12시간 환류시켜 반응을 진행한다. 반응 종료 후, 상온에서 식히고 EA/증류수로 추출하여 유기층을 분리한다. 분리한 유기층의 용매를 모두 날린 후, 컬럼크로마토그래피로 정제하여 아래의 중간체 (k)를 얻는다.Referring to the reaction equation, in a 500mL two-neck flask under a nitrogen atmosphere, tthe intermediate (j) (1.23g, 0.002mol), 9,10-Bis (4,4,5,5-tetramethyl[1.3.2] After adding dioxaborolan-2-yl)anthracene (0.86g, 0.002mol) and Pd(PPh 3 ) 4 (0.2g, 0.0002mol), add THF (100mL) and stir. When all substances in the flask are dissolved, add potassium carbonate solution (2N, 100 mL). The reaction proceeds by refluxing at 80 ° C. for 12 hours. After completion of the reaction, the mixture was cooled at room temperature and extracted with EA/distilled water to separate an organic layer. After removing all the solvent from the separated organic layer, it is purified by column chromatography to obtain the intermediate (k) below.

중간체(k)Intermediate (k)

Figure 112020131688418-pat00055
Figure 112020131688418-pat00055

(12) 중간체(l) (12) Intermediate (l)

Figure 112020131688418-pat00056
Figure 112020131688418-pat00056

상기 반응식을 참조하면, 질소 분위기 하에서 500mL two-neck 플라스크에, 1,6-dibromopyrene(1.43g, 4mmol), 상기 중간체(b)(1.2g, 4mmol), Pd(PPh3)4 (0.2g, 0.0002mol)를 넣고, THF(100mL)를 넣어 교반시킨다. 플라스크 안에 물질이 모두 녹으면 potassium carbonate solution(2N, 100mL)를 넣는다. 80℃ 에서 12시 간 동안 환류시켜 반응을 진행한다. 반응 종료 후, 상온에서 식히고 ethyl acetate/증류수로 추출하여 유기층을 분리한다. 분리한 유기층의 용매를 모두 날린 후, 컬럼크로마토그래피로 정제하여 아래의 중간체 (l)을 얻는다.Referring to the above reaction scheme, in a 500mL two-neck flask under a nitrogen atmosphere, 1,6-dibromopyrene (1.43g, 4mmol), the intermediate (b) (1.2g, 4mmol), Pd (PPh 3 ) 4 (0.2g, 0.0002 mol) was added, and THF (100 mL) was added and stirred. When all substances in the flask are dissolved, add potassium carbonate solution (2N, 100mL). The reaction proceeds by refluxing at 80 ° C. for 12 hours. After completion of the reaction, the mixture was cooled at room temperature and extracted with ethyl acetate/distilled water to separate an organic layer. After removing all the solvent from the separated organic layer, it is purified by column chromatography to obtain the intermediate (l) below.

중간체(l)Intermediate (l)

Figure 112020131688418-pat00057
Figure 112020131688418-pat00057

(13) 중간체(m) (13) Intermediates (m)

Figure 112020131688418-pat00058
Figure 112020131688418-pat00058

상기 반응식을 참조하면, 질소 분위기 하에서 500mL two-neck 플라스크에, 2,7-dibromo-9,9-dimethyl-9H-fluorene(1.41g, 4mmol), 상기 중간체(b)(1.2g, 4mmol), Pd(PPh3)4(0.2g, 0.0002mol)를 넣고, THF(100mL)를 넣어 교반시킨다. 플라스크 안에 물질이 모두 녹으면 potassium carbonate solution(2N, 100mL)를 넣는다. 80℃ 에서 12시간 동안 환류시켜 반응을 진행한다. 반응 종료 후, 상온에서 식히고 ethyl acetate/증류수로 추출하여 유기층을 분리한다. 분리한 유기층의 용매를 모두 날린 후, 컬럼크로마토그래피로 정제하여 아래의 중간체 (m)을 얻는다.Referring to the above reaction scheme, in a 500mL two-neck flask under a nitrogen atmosphere, 2,7-dibromo-9,9-dimethyl-9H-fluorene (1.41g, 4mmol), the intermediate (b) (1.2g, 4mmol), After adding Pd(PPh 3 ) 4 (0.2g, 0.0002mol), add THF (100mL) and stir. When all substances in the flask are dissolved, add potassium carbonate solution (2N, 100mL). The reaction proceeds by refluxing at 80 ° C. for 12 hours. After completion of the reaction, the mixture was cooled at room temperature and extracted with ethyl acetate/distilled water to separate an organic layer. After removing all the solvent of the separated organic layer, it was purified by column chromatography to obtain the intermediate (m) below.

중간체(m)intermediate (m)

Figure 112020131688418-pat00059
Figure 112020131688418-pat00059

(14) 중간체(n) (14) Intermediate (n)

Figure 112020131688418-pat00060
Figure 112020131688418-pat00060

상기 반응식을 참조하면, 3-(7-butoxybicyclo[4.2.0]octa-1(6),2,4-trien-3-yl)-9H-carbazole(1.71g, 5mmol), P(t-Bu)3(0.04g, 0.22mmol), Pd2(dba)3(0.11g, 0.12mmol), 1,3,5-tribromobenzene(0.63g, 2mmol), 그리고 tert-butoxide(1.0g, 10.6mmol)을 toluene(30mL)에 용해시킨다. 100℃에서 20시간 동안 반응시킨다. 반응 종료 후, 실온에서 냉각시킨다. 냉각된 혼합물을 dichloromethane으로 추출한 후에 MgSO4로 건조시킨다. 컬럼 크로마토그래피로 정제하여 아래의 중간체 (n)을 얻는다.Referring to the above reaction scheme, 3-(7-butoxybicyclo[4.2.0]octa-1(6),2,4-trien-3-yl)-9H-carbazole (1.71g, 5mmol), P(t-Bu ) 3 (0.04g, 0.22mmol), Pd 2 (dba) 3 (0.11g, 0.12mmol), 1,3,5-tribromobenzene (0.63g, 2mmol), and tert-butoxide (1.0g, 10.6mmol) Dissolve in toluene (30mL). React for 20 hours at 100 °C. After completion of the reaction, it is cooled at room temperature. The cooled mixture was extracted with dichloromethane and dried with MgSO 4 . Purification by column chromatography gives the intermediate (n) below.

중간체(n)intermediate (n)

Figure 112020131688418-pat00061
Figure 112020131688418-pat00061

(15) 중간체(o) (15) Intermediates (o)

Figure 112020131688418-pat00062
Figure 112020131688418-pat00062

상기 반응식을 참조하면, 질소 분위기 하에서 500mL two-neck 플라스크에, 2,15-dibromotetraphenylene(1.85g, 4mmol), 상기 중간체(b)(1.2g, 4mmol), Pd(PPh3)4(0.2g, 0.0002mol)를 넣고, THF(100mL)를 넣어 교반시킨다. 플라스크 안에 물질이 모두 녹으면 potassium carbonate solution(2N, 100mL)를 넣는다. 80℃에서 12시간 동안 환류시켜 반응을 진행한다. 반응 종료 후, 상온에서 식히고 ethyl acetate/증류수로 추출하여 유기층을 분리한다. 분리한 유기층의 용매를 모두 날린 후, 컬럼크로마토그래피로 정제하여 아래의 중간체 (o)를 얻는다.Referring to the reaction scheme, in a 500mL two-neck flask under a nitrogen atmosphere, 2,15-dibromotetraphenylene (1.85g, 4mmol), the intermediate (b) (1.2g, 4mmol), Pd (PPh 3 ) 4 (0.2g, 0.0002 mol) was added, and THF (100 mL) was added and stirred. When all substances in the flask are dissolved, add potassium carbonate solution (2N, 100mL). The reaction proceeds by refluxing at 80 ° C. for 12 hours. After completion of the reaction, the mixture was cooled at room temperature and extracted with ethyl acetate/distilled water to separate an organic layer. After removing all the solvent from the separated organic layer, it is purified by column chromatography to obtain the intermediate (o) below.

중간체(o)intermediate (o)

Figure 112020131688418-pat00063
Figure 112020131688418-pat00063

(16) 중간체(p) (16) Intermediate (p)

Figure 112020131688418-pat00064
Figure 112020131688418-pat00064

상기 반응식을 참조하면, 질소 분위기 하에서 500mL two-neck 플라스크에 5-bromo-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine(1.13g, 4mmol), 상기 중간체(h)(0.91g, 4mmol), Pd(PPh3)4(0.2g, 0.0002mol)를 넣고, THF(100mL)를 넣어 교반시킨다. 플라스크 안에 물질이 모두 녹으면 potassium carbonate solution(2N, 100mL)를 넣는다. 80℃에서 12시간 동안 환류시켜 반응을 진행한다. 반응 종료 후, 상온에서 식히고 ethyl acetate/증류수로 추출하여 유기층을 분리한다. 분리한 유기층의 용매를 모두 날린 후, 컬럼크로마토그래피로 정제하여 아래의 중간체 (p)를 얻는다.Referring to the above reaction scheme, 5-bromo-2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridine (1.13 g, 4 mmol) was added to a 500 mL two-neck flask under a nitrogen atmosphere. ), the above intermediate (h) (0.91g, 4mmol), Pd(PPh 3 ) 4 (0.2g, 0.0002mol) were added, and THF (100mL) was added and stirred. When all substances in the flask are dissolved, add potassium carbonate solution (2N, 100mL). The reaction proceeds by refluxing at 80 ° C. for 12 hours. After completion of the reaction, the mixture was cooled at room temperature and extracted with ethyl acetate/distilled water to separate an organic layer. After removing all the solvent of the separated organic layer, it is purified by column chromatography to obtain the intermediate (p) below.

중간체(p)Intermediate (p)

Figure 112020131688418-pat00065
Figure 112020131688418-pat00065

(17) 중간체(q) (17) Intermediate (q)

Figure 112020131688418-pat00066
Figure 112020131688418-pat00066

상기 반응식을 참조하면, 질소 분위기 하에서 500mL two-neck 플라스크에, 중간체(p)(0.61g, 0.002mol), 9,10-Bis(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)anthracene(0.86g, 0.002mol), Pd(PPh3)4(0.2g, 0.0002mol)를 넣고, THF (100mL)를 넣어 교반시킨다. 플라스크 안에 물질이 모두 녹으면 potassium carbonate solution(2N, 100 mL)를 넣는다. 80℃에서 12시간 환류시켜 반응을 진행한다. 반응 종료 후, 상온에서 식히고 EA/증류수로 추출하여 유기층을 분리한다. 분리한 유기층의 용매를 모두 날린 후, 컬럼크로마토그래피로 정제하여 아래의 중간체 (q)를 얻는다.Referring to the above reaction scheme, in a 500mL two-neck flask under a nitrogen atmosphere, intermediate (p) (0.61g, 0.002mol), 9,10-Bis (4,4,5,5-tetramethyl[1.3.2]dioxaborolan- 2-yl)anthracene (0.86g, 0.002mol) and Pd(PPh 3 ) 4 (0.2g, 0.0002mol) were added, and THF (100mL) was added and stirred. When all substances in the flask are dissolved, add potassium carbonate solution (2N, 100 mL). The reaction proceeds by refluxing at 80 ° C. for 12 hours. After completion of the reaction, the mixture was cooled at room temperature and extracted with EA/distilled water to separate an organic layer. After removing all the solvent from the separated organic layer, it is purified by column chromatography to obtain the intermediate (q) below.

중간체(q)Intermediate (q)

Figure 112020131688418-pat00067
Figure 112020131688418-pat00067

<실시예 1><Example 1>

아래의 반응식을 통해 상기 [화학식 1]의 유기화합물을 합성하였다. The organic compound of [Formula 1] was synthesized through the following reaction scheme.

Figure 112020131688418-pat00068
Figure 112020131688418-pat00068

질소 분위기 하에서 500mL two-neck 플라스크에, 상기 중간체 (c)(1.0g, 0.002mol), 9,10-Bis(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)anthracene (0.43g, 0.001mol), Pd(PPh3)4(0.2g, 0.0002mol)를 넣고, THF(100mL)를 넣어 교반시킨다. 플라스크 안에 물질이 모두 녹으면 potassium carbonate solution (2N, 100 mL)를 넣는다. 80℃에서 12시간 환류시켜 반응을 진행한다. 반응 종료 후, 상온에서 식히고 EA/증류수로 추출하여 유기층을 분리한다. 분리한 유기층의 용매를 모두 날린 후, 컬럼크로마토그래피로 정제하여 아래 [화학식 1]의 유기화합물을 얻는다.In a 500 mL two-neck flask under a nitrogen atmosphere, the intermediate (c) (1.0 g, 0.002 mol), 9,10-Bis (4,4,5,5-tetramethyl [1.3.2] dioxaborolan-2-yl) anthracene (0.43g, 0.001mol) and Pd(PPh 3 ) 4 (0.2g, 0.0002mol) were added, and THF (100mL) was added and stirred. When all substances in the flask are dissolved, add potassium carbonate solution (2N, 100 mL). The reaction proceeds by refluxing at 80 ° C. for 12 hours. After completion of the reaction, the mixture was cooled at room temperature and extracted with EA/distilled water to separate an organic layer. After removing all the solvent of the separated organic layer, it is purified by column chromatography to obtain an organic compound represented by the following [Chemical Formula 1].

[화학식 1][Formula 1]

Figure 112020131688418-pat00069
Figure 112020131688418-pat00069

<실시예 2><Example 2>

아래의 반응식을 통해 상기 [화학식 2]의 유기화합물을 합성하였다. The organic compound of [Formula 2] was synthesized through the following reaction scheme.

Figure 112020131688418-pat00070
Figure 112020131688418-pat00070

질소 분위기 하에서 500mL two-neck 플라스크에, 상기 중간체 (c)(1.0g, 0.002mol), 9,10-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)anthracene(0.58g, 0.001mol), Pd(PPh3)4(0.2g, 0.0002mol)를 넣고, THF (100mL)를 넣어 교반시킨다. 플라스크 안에 물질이 모두 녹으면 potassium carbonate solution(2N, 100mL)를 넣는다. 80℃에서 12시간 환류시켜 반응을 진행한다. 반응 종료 후, 상온에서 식히고 EA/증류수로 추출하여 유기층을 분리한다. 분리한 유기층의 용매를 모두 날린 후, 컬럼크로마토그래피로 정제하여 아래 [화학식 2]의 유기화합물을 얻는다.In a 500mL two-neck flask under a nitrogen atmosphere, the intermediate (c) (1.0g, 0.002mol), 9,10-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl)phenyl)anthracene (0.58g, 0.001mol) and Pd(PPh 3 ) 4 (0.2g, 0.0002mol) were added, and THF (100mL) was added and stirred. When all substances in the flask are dissolved, add potassium carbonate solution (2N, 100mL). The reaction proceeds by refluxing at 80 ° C. for 12 hours. After completion of the reaction, the mixture was cooled at room temperature and extracted with EA/distilled water to separate an organic layer. After removing all the solvent of the separated organic layer, it is purified by column chromatography to obtain an organic compound represented by [Chemical Formula 2] below.

[화학식 2][Formula 2]

Figure 112020131688418-pat00071
Figure 112020131688418-pat00071

<실시예 3><Example 3>

아래의 반응식을 통해 상기 [화학식 3]의 유기화합물을 합성하였다. The organic compound of [Formula 3] was synthesized through the following reaction scheme.

Figure 112020131688418-pat00072
Figure 112020131688418-pat00072

질소 분위기 하에서 500mL two-neck 플라스크에, 상기 중간체 (e)(1.5g, 0.002mol), 상기 중간체 (f)(0.84g, 0.002mol), Pd(PPh3)4(0.2g, 0.0002mol)를 넣고, THF(100mL)를 넣어 교반시킨다. 플라스크 안에 물질이 모두 녹으면 potassium carbonate solution(2N, 100 mL)를 넣는다. 80℃에서 12시간 환류시켜 반응을 진행한다. 반응 종료 후, 상온에서 식히고 EA/증류수로 추출하여 유기층을 분리한다. 분리한 유기층의 용매를 모두 날린 후, 컬럼크로마토그래피로 정제하여 아래 [화학식 3]의 유기화합물을 얻는다.In a 500mL two-neck flask under a nitrogen atmosphere, the intermediate (e) (1.5g, 0.002mol), the intermediate (f) (0.84g, 0.002mol), and Pd(PPh 3 ) 4 (0.2g, 0.0002mol) were mixed. was added, and THF (100 mL) was added and stirred. When all substances in the flask are dissolved, add potassium carbonate solution (2N, 100 mL). The reaction proceeds by refluxing at 80 ° C. for 12 hours. After completion of the reaction, the mixture was cooled at room temperature and extracted with EA/distilled water to separate an organic layer. After removing all the solvent of the separated organic layer, it is purified by column chromatography to obtain an organic compound represented by [Chemical Formula 3] below.

[화학식 3][Formula 3]

Figure 112020131688418-pat00073
Figure 112020131688418-pat00073

<실시예 4><Example 4>

아래의 반응식을 통해 상기 [화학식 4]의 유기화합물을 합성하였다. The organic compound of [Formula 4] was synthesized through the following reaction scheme.

Figure 112020131688418-pat00074
Figure 112020131688418-pat00074

질소 분위기 하에서 500mL two-neck 플라스크에, 상기 중간체 (d)(1.0g, 0.002mol), 9,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anthracene (0.76g, 0.001mol), Pd(PPh3)4(0.2g, 0.0002mol)를 넣고, THF(100mL)를 넣어 교반시킨다. 플라스크 안에 물질이 모두 녹으면 potassium carbonzte solution(2N, 100 mL)를 넣는다. 80℃에서 12시간 환류시켜 반응을 진행한다. 반응 종료 후, 상온에서 식히고 EA/증류수로 추출하여 유기층을 분리한다. 분리한 유기층의 용매를 모두 날린 후, 컬럼크로마토그래피로 정제하여 아래 [화학식 4]의 유기화합물을 얻는다.In a 500 mL two-neck flask under a nitrogen atmosphere, the intermediate (d) (1.0 g, 0.002 mol), 9,10-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl ) Anthracene (0.76g, 0.001mol), Pd(PPh 3 ) 4 (0.2g, 0.0002mol) were added, and THF (100mL) was added and stirred. When all substances in the flask are dissolved, add potassium carbonzte solution (2N, 100 mL). The reaction proceeds by refluxing at 80 ° C. for 12 hours. After completion of the reaction, the mixture was cooled at room temperature and extracted with EA/distilled water to separate an organic layer. After removing all the solvent of the separated organic layer, it is purified by column chromatography to obtain an organic compound represented by the following [Chemical Formula 4].

[화학식 4][Formula 4]

Figure 112020131688418-pat00075
Figure 112020131688418-pat00075

<실시예 5><Example 5>

아래의 반응식을 통해 상기 [화학식 5]의 유기화합물을 합성하였다. The organic compound of [Chemical Formula 5] was synthesized through the following reaction scheme.

Figure 112020131688418-pat00076
Figure 112020131688418-pat00076

질소 분위기 하에서 500mL two-neck 플라스크에, 상기 중간체 (g)(1.48g, 0.002mol), 상기 중간체 (d)(1.0g, 0.002mol), Pd(PPh3)4(0.2g, 0.0002mol)를 넣고, THF(100mL)를 넣어 교반시킨다. 플라스크 안에 물질이 모두 녹으면 potassium carbonate solution(2N, 100 mL)를 넣는다. 80℃에서 12시간 환류시켜 반응을 진행한다. 반응 종료 후, 상온에서 식히고 EA/증류수로 추출하여 유기층을 분리한다. 분리한 유기층의 용매를 모두 날린 후, 컬럼크로마토그래피로 정제하여 아래 [화학식 5]의 유기화합물을 얻는다.In a 500mL two-neck flask under a nitrogen atmosphere, the intermediate (g) (1.48g, 0.002mol), the intermediate (d) (1.0g, 0.002mol), and Pd(PPh 3 ) 4 (0.2g, 0.0002mol) were mixed. was added, and THF (100 mL) was added and stirred. When all substances in the flask are dissolved, add potassium carbonate solution (2N, 100 mL). The reaction proceeds by refluxing at 80 ° C. for 12 hours. After completion of the reaction, the mixture was cooled at room temperature and extracted with EA/distilled water to separate an organic layer. After removing all the solvent of the separated organic layer, it is purified by column chromatography to obtain an organic compound represented by the following [Chemical Formula 5].

[화학식 5][Formula 5]

Figure 112020131688418-pat00077
Figure 112020131688418-pat00077

<실시예 6><Example 6>

아래의 반응식을 통해 상기 [화학식 6]의 유기화합물을 합성하였다. The organic compound of [Chemical Formula 6] was synthesized through the following reaction scheme.

Figure 112020131688418-pat00078
Figure 112020131688418-pat00078

질소 분위기 하에서 500mL two-neck 플라스크에, 상기 중간체 (j)(1.23g, 0.002mol), 9,10-Bis(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)anthracene (0.43g, 0.001mol), Pd(PPh3)4(0.2g, 0.0002mol)를 넣고, THF(100mL)를 넣어 교반시킨다. 플라스크 안에 물질이 모두 녹으면 potassium carbonate solution(2N, 100 mL)를 넣는다. 80℃에서 12시간 환류시켜 반응을 진행한다. 반응 종료 후, 상온에서 식히고 EA/증류수로 추출하여 유기층을 분리한다. 분리한 유기층의 용매를 모두 날린 후, 컬럼크로마토그래피로 정제하여 아래 [화학식 6]의 유기화합물을 얻는다.In a 500 mL two-neck flask under a nitrogen atmosphere, the above intermediate (j) (1.23 g, 0.002 mol), 9,10-Bis (4,4,5,5-tetramethyl [1.3.2] dioxaborolan-2-yl) anthracene (0.43g, 0.001mol) and Pd(PPh 3 ) 4 (0.2g, 0.0002mol) were added, and THF (100mL) was added and stirred. When all substances in the flask are dissolved, add potassium carbonate solution (2N, 100 mL). The reaction proceeds by refluxing at 80 ° C. for 12 hours. After completion of the reaction, the mixture was cooled at room temperature and extracted with EA/distilled water to separate an organic layer. After removing all the solvent of the separated organic layer, it is purified by column chromatography to obtain an organic compound represented by [Chemical Formula 6] below.

[화학식 6][Formula 6]

Figure 112020131688418-pat00079
Figure 112020131688418-pat00079

<실시예 7><Example 7>

아래의 반응식을 통해 상기 [화학식 7]의 유기화합물을 합성하였다. The organic compound of [Chemical Formula 7] was synthesized through the following reaction scheme.

Figure 112020131688418-pat00080
Figure 112020131688418-pat00080

질소 분위기 하에서 500mL two-neck 플라스크에, 상기 중간체 (k)(1.68g, 0.002mol), 상기 중간체 (c)(1.01g, 0.002mol), Pd(PPh3)4(0.2g, 0.0002mol)를 넣고, THF(100mL)를 넣어 교반시킨다. 플라스크 안에 물질이 모두 녹으면 potassium carbonate solution (2N, 100 mL)를 넣는다. 80℃에서 12시간 환류시켜 반응을 진행한다. 반응 종료 후, 상온에서 식히고 EA/증류수로 추출하여 유기층을 분리한다. 분리한 유기층의 용매를 모두 날린 후, 컬럼크로마토그래피로 정제하여 아래 [화학식 7]의 유기화합물을 얻는다.The intermediate (k) (1.68 g, 0.002 mol), the intermediate (c) (1.01 g, 0.002 mol), and Pd(PPh 3 ) 4 (0.2 g, 0.0002 mol) were mixed in a 500 mL two-neck flask under a nitrogen atmosphere. was added, and THF (100 mL) was added and stirred. When all substances in the flask are dissolved, add potassium carbonate solution (2N, 100 mL). The reaction proceeds by refluxing at 80 ° C. for 12 hours. After completion of the reaction, the mixture was cooled at room temperature and extracted with EA/distilled water to separate an organic layer. After removing all the solvent of the separated organic layer, it is purified by column chromatography to obtain an organic compound represented by the following [Chemical Formula 7].

[화학식 7][Formula 7]

Figure 112020131688418-pat00081
Figure 112020131688418-pat00081

<실시예 8><Example 8>

아래의 반응식을 통해 상기 [화학식 8]의 유기화합물을 합성하였다. The organic compound of [Chemical Formula 8] was synthesized through the following reaction scheme.

Figure 112020131688418-pat00082
Figure 112020131688418-pat00082

질소 분위기 하에서 500mL two-neck 플라스크에, 상기 중간체 (k)(1.68g, 0.002mol), 상기 중간체(l)(0.91g, 0.002mol), Pd(PPh3)4(0.2g, 0.0002mol)를 넣고, THF(100mL)를 넣어 교반시킨다. 플라스크 안에 물질이 모두 녹으면 potassium carbonate solution(2N, 100 mL)를 넣는다. 80℃에서 12시간 환류시켜 반응을 진행한다. 반응 종료 후, 상온에서 식히고 EA/증류수로 추출하여 유기층을 분리한다. 분리한 유기층의 용매를 모두 날린 후, 컬럼크로마토그래피로 정제하여 아래 [화학식 8]의 유기화합물을 얻는다.In a 500mL two-neck flask under a nitrogen atmosphere, the intermediate (k) (1.68g, 0.002mol), the intermediate (l) (0.91g, 0.002mol), and Pd(PPh 3 ) 4 (0.2g, 0.0002mol) were mixed. was added, and THF (100 mL) was added and stirred. When all substances in the flask are dissolved, add potassium carbonate solution (2N, 100 mL). The reaction proceeds by refluxing at 80 ° C. for 12 hours. After completion of the reaction, the mixture was cooled at room temperature and extracted with EA/distilled water to separate an organic layer. After removing all the solvent of the separated organic layer, it is purified by column chromatography to obtain an organic compound represented by [Chemical Formula 8] below.

[화학식 8][Formula 8]

Figure 112020131688418-pat00083
Figure 112020131688418-pat00083

<실시예 9><Example 9>

아래의 반응식을 통해 상기 [화학식 9]의 유기화합물을 합성하였다. The organic compound of [Chemical Formula 9] was synthesized through the following reaction scheme.

Figure 112020131688418-pat00084
Figure 112020131688418-pat00084

질소 분위기 하에서 500mL two-neck 플라스크에, 상기 중간체 (a)(0.51g, 0.002mol), 9,10-Bis(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)anthracene (0.43g, 0.001mol), Pd(PPh3)4(0.2g, 0.0002mol)를 넣고, THF(100mL)를 넣어 교반시킨다. 플라스크 안에 물질이 모두 녹으면 potassium carbonate solution(2N, 100 mL)를 넣는다. 80℃에서 12시간 환류시켜 반응을 진행한다. 반응 종료 후, 상온에서 식히고 EA/증류수로 추출하여 유기층을 분리한다. 분리한 유기층의 용매를 모두 날린 후, 컬럼크로마토그래피로 정제하여 아래 [화학식 9]의 유기화합물을 얻는다.In a 500 mL two-neck flask under a nitrogen atmosphere, the intermediate (a) (0.51 g, 0.002 mol), 9,10-Bis (4,4,5,5-tetramethyl [1.3.2] dioxaborolan-2-yl) anthracene (0.43g, 0.001mol) and Pd(PPh 3 ) 4 (0.2g, 0.0002mol) were added, and THF (100mL) was added and stirred. When all substances in the flask are dissolved, add potassium carbonate solution (2N, 100 mL). The reaction proceeds by refluxing at 80 ° C. for 12 hours. After completion of the reaction, the mixture was cooled at room temperature and extracted with EA/distilled water to separate an organic layer. After removing all the solvent of the separated organic layer, it is purified by column chromatography to obtain an organic compound represented by [Chemical Formula 9] below.

[화학식 9][Formula 9]

Figure 112020131688418-pat00085
Figure 112020131688418-pat00085

<실시예 10><Example 10>

아래의 반응식을 통해 상기 [화학식 10]의 유기화합물을 합성하였다. The organic compound of [Formula 10] was synthesized through the following reaction scheme.

Figure 112020131688418-pat00086
Figure 112020131688418-pat00086

질소 분위기 하에서 500mL two-neck 플라스크에, 상기 중간체 (m)(0.89g, 0.002mol), 9,10-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)anthracene(0.58g, 0.001mol), Pd(PPh3)4(0.2g, 0.0002mol)를 넣고, THF (100mL)를 넣어 교반시킨다. 플라스크 안에 물질이 모두 녹으면 potassium carbonate solution (2N, 100 mL)를 넣는다. 80℃에서 12시간 환류시켜 반응을 진행한다. 반응 종료 후, 상온에서 식히고 EA/증류수로 추출하여 유기층을 분리한다. 분리한 유기층의 용매를 모두 날린 후, 컬럼크로마토그래피로 정제하여 아래 [화학식 10]의 유기화합물을 얻는다.In a 500mL two-neck flask under a nitrogen atmosphere, the intermediate (m) (0.89g, 0.002mol), 9,10-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl)phenyl)anthracene (0.58g, 0.001mol) and Pd(PPh 3 ) 4 (0.2g, 0.0002mol) were added, and THF (100mL) was added and stirred. When all substances in the flask are dissolved, add potassium carbonate solution (2N, 100 mL). The reaction proceeds by refluxing at 80 ° C. for 12 hours. After completion of the reaction, the mixture was cooled at room temperature and extracted with EA/distilled water to separate an organic layer. After removing all the solvent of the separated organic layer, it is purified by column chromatography to obtain an organic compound represented by [Chemical Formula 10] below.

[화학식 10][Formula 10]

Figure 112020131688418-pat00087
Figure 112020131688418-pat00087

<실시예 11><Example 11>

아래의 반응식을 통해 상기 [화학식 11]의 유기화합물을 합성하였다. The organic compound of [Chemical Formula 11] was synthesized through the following reaction scheme.

Figure 112020131688418-pat00088
Figure 112020131688418-pat00088

질소 분위기 하에서 500mL two-neck 플라스크에, 2-(10-(4-(7-butoxybicyclo[4.2.0]octa-1(6),2,4-trien-3-yl)phenyl)anthracen-9-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(1.11g, 0.002mol), 상기 중간체 (f)(0.84g, 0.002mol), Pd(PPh3)4(0.2g, 0.0002mol)를 넣고, THF(100mL)를 넣어 교반시킨다. 플라스크 안에 물질이 모두 녹으면 potassium carbonate solution (2N, 100mL)를 넣는다. 80℃에서 12시간 환류시켜 반응을 진행한다. 반응 종료 후, 상온에서 식히고 EA/증류수로 추출하여 유기층을 분리한다. 분리한 유기층의 용매를 모두 날린 후, 컬럼크로마토그래피로 정제하여 아래 [화학식 11]의 유기화합물을 얻는다.In a 500 mL two-neck flask under a nitrogen atmosphere, 2-(10-(4-(7-butoxybicyclo[4.2.0]octa-1(6),2,4-trien-3-yl)phenyl)anthracen-9- yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.11 g, 0.002 mol), the intermediate (f) (0.84 g, 0.002 mol), Pd (PPh 3 ) 4 (0.2 g , 0.0002 mol) was added, and THF (100 mL) was added and stirred. When all substances in the flask are dissolved, add potassium carbonate solution (2N, 100mL). The reaction proceeds by refluxing at 80 ° C. for 12 hours. After completion of the reaction, the mixture was cooled at room temperature and extracted with EA/distilled water to separate an organic layer. After removing all the solvent of the separated organic layer, it is purified by column chromatography to obtain an organic compound represented by [Chemical Formula 11] below.

[화학식 11][Formula 11]

Figure 112020131688418-pat00089
Figure 112020131688418-pat00089

<실시예 12><Example 12>

아래의 반응식을 통해 상기 [화학식 12]의 유기화합물을 합성하였다. The organic compound of [Chemical Formula 12] was synthesized through the following reaction scheme.

Figure 112020131688418-pat00090
Figure 112020131688418-pat00090

질소 분위기 하에서 500mL two-neck 플라스크에, 상기 중간체 (n)(1.67g, 0.002mol), 9,10-Bis(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)anthracene (0.43g, 0.001mol), Pd(PPh3)4(0.2g, 0.0002mol)를 넣고, THF(100mL)를 넣어 교반시킨다. 플라스크 안에 물질이 모두 녹으면 potassium carbonate solution(2N, 100 mL)를 넣는다. 80℃에서 12시간 환류시켜 반응을 진행한다. 반응 종료 후, 상온에서 식히고 EA/증류수로 추출하여 유기층을 분리한다. 분리한 유기층의 용매를 모두 날린 후, 컬럼크로마토그래피로 정제하여 아래 [화학식 12]의 유기화합물을 얻는다.In a 500 mL two-neck flask under a nitrogen atmosphere, the intermediate (n) (1.67 g, 0.002 mol), 9,10-Bis (4,4,5,5-tetramethyl [1.3.2] dioxaborolan-2-yl) anthracene (0.43g, 0.001mol) and Pd(PPh 3 ) 4 (0.2g, 0.0002mol) were added, and THF (100mL) was added and stirred. When all substances in the flask are dissolved, add potassium carbonate solution (2N, 100 mL). The reaction proceeds by refluxing at 80 ° C. for 12 hours. After completion of the reaction, the mixture was cooled at room temperature and extracted with EA/distilled water to separate an organic layer. After removing all the solvent of the separated organic layer, it is purified by column chromatography to obtain an organic compound represented by [Chemical Formula 12] below.

[화학식 12][Formula 12]

Figure 112020131688418-pat00091
Figure 112020131688418-pat00091

<실시예 13><Example 13>

아래의 반응식을 통해 상기 [화학식 13]의 유기화합물을 합성하였다. The organic compound of [Formula 13] was synthesized through the following reaction scheme.

Figure 112020131688418-pat00092
Figure 112020131688418-pat00092

질소 분위기 하에서 500mL two-neck 플라스크에, 상기 중간체 (o)(1.11g, 0.002mol), 9,10-Bis(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)anthracene (0.43g, 0.001mol), Pd(PPh3)4(0.2g, 0.0002mol)를 넣고, THF(100mL)를 넣어 교반시킨다. 플라스크 안에 물질이 모두 녹으면 potassium carbonate solution(2N, 100 mL)를 넣는다. 80℃에서 12시간 환류시켜 반응을 진행한다. 반응 종료 후, 상온에서 식히고 EA/증류수로 추출하여 유기층을 분리한다. 분리한 유기층의 용매를 모두 날린 후, 컬럼크로마토그래피로 정제하여 아래 [화학식 13]의 유기화합물을 얻는다.In a 500 mL two-neck flask under a nitrogen atmosphere, the intermediate (o) (1.11 g, 0.002 mol), 9,10-Bis (4,4,5,5-tetramethyl [1.3.2] dioxaborolan-2-yl) anthracene (0.43g, 0.001mol) and Pd(PPh 3 ) 4 (0.2g, 0.0002mol) were added, and THF (100mL) was added and stirred. When all substances in the flask are dissolved, add potassium carbonate solution (2N, 100 mL). The reaction proceeds by refluxing at 80 ° C. for 12 hours. After completion of the reaction, the mixture was cooled at room temperature and extracted with EA/distilled water to separate an organic layer. After removing all the solvent of the separated organic layer, it is purified by column chromatography to obtain an organic compound represented by [Chemical Formula 13] below.

[화학식 13][Formula 13]

Figure 112020131688418-pat00093
Figure 112020131688418-pat00093

<실시예 14><Example 14>

아래의 반응식을 통해 상기 [화학식 14]의 유기화합물을 합성하였다. The organic compound of [Formula 14] was synthesized through the following reaction scheme.

Figure 112020131688418-pat00094
Figure 112020131688418-pat00094

질소 분위기 하에서 500mL two-neck 플라스크에, 상기 중간체 (q)(1.05g, 0.002mol), 상기 중간체 (c)(1.01g, 0.002mol), Pd(PPh3)4(0.2g, 0.0002mol)를 넣고, THF(100mL)를 넣어 교반시킨다. 플라스크 안에 물질이 모두 녹으면 potassium carbonate solution(2N, 100 mL)를 넣는다. 80℃에서 12시간 환류시켜 반응을 진행한다. 반응 종료 후, 상온에서 식히고 EA/증류수로 추출하여 유기층을 분리한다. 분리한 유기층의 용매를 모두 날린 후, 컬럼크로마토그래피로 정제하여 아래 [화학식 14]의 유기화합물을 얻는다.The intermediate (q) (1.05 g, 0.002 mol), the intermediate (c) (1.01 g, 0.002 mol), and Pd(PPh 3 ) 4 (0.2 g, 0.0002 mol) were mixed in a 500 mL two-neck flask under a nitrogen atmosphere. was added, and THF (100 mL) was added and stirred. When all substances in the flask are dissolved, add potassium carbonate solution (2N, 100 mL). The reaction proceeds by refluxing at 80 ° C. for 12 hours. After completion of the reaction, the mixture was cooled at room temperature and extracted with EA/distilled water to separate an organic layer. After removing all the solvent of the separated organic layer, it is purified by column chromatography to obtain an organic compound represented by the following [Chemical Formula 14].

[화학식 14][Formula 14]

Figure 112020131688418-pat00095
Figure 112020131688418-pat00095

Claims (26)

유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물으로서,
상기 유기화합물은, 아래 [구조식 A]로부터 선택된 적어도 하나의 화합물을 포함하는 것을 특징으로 하는 유기화합물.
[구조식 A]
Figure 112022061957006-pat00096

상기 [구조식 A]에서, R1, R2는 서로 같거나 상이하고, 각각 독립적으로 수소, 알킬기(alkyl group), 치환된 알킬기(alkyl group), 헤테로사이클로기(heterocyclic group), 치환된 헤테로사이클로기(heterocyclic group), 아릴기(aryl group), 치환된 아릴기(aryl group), 아민기(amine group), 피리딘기(pyridine group), 피리미딘기(pyrimidine group), 트이라졸기(triazole group), 트리아진기(triazine group), 포스파인기(phosphine group), 시릴기(silole group), 아릴아민기(arylamine), 카바졸기(carbazole) 또는 치환된 카바졸기로부터 선택되고;
상기 X1, X2는 서로 같거나 상이하고, 각각 독립적으로 알킬기(alkyl group), 치환된 알킬기(alkyl group), 헤테로사이클로기(heterocyclic group), 치환된 헤테로사이클로기(heterocyclic group)로부터 선택될 수 있고;
상기 R1, R2, X1, X2중 선택된 적어도 1곳 이상에는 아래 [구조식 B]의 벤조시클로부텐기(benzocyclobutene)가 직접 적용되거나 수소, 알킬기(alkyl group), 치환된 알킬기(alkyl group), 헤테로사이클로기(heterocyclic group), 치환된 헤테로사이클로기(heterocyclic group), 아릴기(aryl group), 치환된 아릴기(aryl group), 아민기(amine group)에 아래 [구조식 B]의 벤조시클로부텐기(benzocyclobutene)로 치환된 유도체가 적용되며;
[구조식 B]
Figure 112022061957006-pat00097

상기 [구조식 B]에서, Y는 수소 또는 탄화수소, C1~C13의 탄소 체인을 가진 알킬기 또는 치환된 알칼기, 수소, 아민 또는 할로겐을 가지고 있는 알킬기이고, X1, X2, X3, X4, X5는 서로 같거나 상이하고, 각각 독립적으로 수소, 탄화수소, 치환된 탄화수소, 할로겐, 시아노, 니트로, 하이드록실, 알콕시, 아민 또는 치환된 아민, 카보닐로부터 선택된다.As an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of the organic electric element,
The organic compound is an organic compound, characterized in that it comprises at least one compound selected from the following [Structural Formula A].
[Structural Formula A]
Figure 112022061957006-pat00096

In [Formula A], R 1 and R 2 are the same as or different from each other, and each independently represents hydrogen, an alkyl group, a substituted alkyl group, a heterocyclic group, or a substituted heterocycle. Heterocyclic group, aryl group, substituted aryl group, amine group, pyridine group, pyrimidine group, triazole group ), a triazine group, a phosphine group, a silole group, an arylamine group, a carbazole group, or a substituted carbazole group;
The X 1 and X 2 are the same as or different from each other, and each independently selected from an alkyl group, a substituted alkyl group, a heterocyclic group, and a substituted heterocyclic group. can;
A benzocyclobutene group of [Structural Formula B] below is directly applied to at least one selected from among R 1 , R 2 , X 1 , and X 2 , or hydrogen, an alkyl group, or a substituted alkyl group ), a heterocyclic group, a substituted heterocyclic group, an aryl group, a substituted aryl group, and an amine group below [Structural Formula B] A derivative substituted with a cyclobutene group (benzocyclobutene) is applied;
[Structural Formula B]
Figure 112022061957006-pat00097

In [Structural Formula B], Y is hydrogen or a hydrocarbon, an alkyl group having a carbon chain of C 1 to C 13 or a substituted alkyl group, hydrogen, an amine or an alkyl group having a halogen, X 1 , X 2 , X 3 , X 4 and X 5 are the same as or different from each other, and are each independently selected from hydrogen, hydrocarbon, substituted hydrocarbon, halogen, cyano, nitro, hydroxyl, alkoxy, amine or substituted amine, and carbonyl. 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물으로서,
상기 유기화합물은, 아래의 화학식을 갖는 것을 특징으로 하는 유기화합물.
Figure 112020131688418-pat00098
As an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of the organic electric element,
The organic compound is an organic compound, characterized in that it has the following chemical formula.
Figure 112020131688418-pat00098
 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물으로서,
상기 유기화합물은, 아래의 화학식을 갖는 것을 특징으로 하는 유기화합물.
Figure 112020131688418-pat00099
As an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of the organic electric element,
The organic compound is an organic compound, characterized in that it has the following chemical formula.
Figure 112020131688418-pat00099
 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물으로서,
상기 유기화합물은, 아래의 화학식을 갖는 것을 특징으로 하는 유기화합물.
Figure 112020131688418-pat00100
As an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of the organic electric element,
The organic compound is an organic compound, characterized in that it has the following chemical formula.
Figure 112020131688418-pat00100
 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물으로서,
상기 유기화합물은, 아래의 화학식을 갖는 것을 특징으로 하는 유기화합물.
Figure 112020131688418-pat00101
As an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of the organic electric element,
The organic compound is an organic compound, characterized in that it has the following chemical formula.
Figure 112020131688418-pat00101
 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물으로서,
상기 유기화합물은, 아래의 화학식을 갖는 것을 특징으로 하는 유기화합물.
Figure 112020131688418-pat00102
As an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of the organic electric element,
The organic compound is an organic compound, characterized in that it has the following chemical formula.
Figure 112020131688418-pat00102
 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물으로서,
상기 유기화합물은, 아래의 화학식을 갖는 것을 특징으로 하는 유기화합물.
Figure 112020131688418-pat00103
As an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of the organic electric element,
The organic compound is an organic compound, characterized in that it has the following chemical formula.
Figure 112020131688418-pat00103
 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물으로서,
상기 유기화합물은, 아래의 화학식을 갖는 것을 특징으로 하는 유기화합물.
Figure 112020131688418-pat00104
As an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of the organic electric element,
The organic compound is an organic compound, characterized in that it has the following chemical formula.
Figure 112020131688418-pat00104
 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물으로서,
상기 유기화합물은, 아래의 화학식을 갖는 것을 특징으로 하는 유기화합물.
Figure 112020131688418-pat00105
As an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of the organic electric element,
The organic compound is an organic compound, characterized in that it has the following chemical formula.
Figure 112020131688418-pat00105
 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물으로서,
상기 유기화합물은, 아래의 화학식을 갖는 것을 특징으로 하는 유기화합물.
Figure 112020131688418-pat00106
As an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of the organic electric element,
The organic compound is an organic compound, characterized in that it has the following chemical formula.
Figure 112020131688418-pat00106
 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물으로서,
상기 유기화합물은, 아래의 화학식을 갖는 것을 특징으로 하는 유기화합물.
Figure 112020131688418-pat00107
As an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of the organic electric element,
The organic compound is an organic compound, characterized in that it has the following chemical formula.
Figure 112020131688418-pat00107
 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물으로서,
상기 유기화합물은, 아래의 화학식을 갖는 것을 특징으로 하는 유기화합물.
Figure 112020131688418-pat00108
As an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of the organic electric element,
The organic compound is an organic compound, characterized in that it has the following chemical formula.
Figure 112020131688418-pat00108
 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물으로서,
상기 유기화합물은, 아래의 화학식을 갖는 것을 특징으로 하는 유기화합물.
Figure 112020131688418-pat00109
As an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of the organic electric element,
The organic compound is an organic compound, characterized in that it has the following chemical formula.
Figure 112020131688418-pat00109
 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물으로서,
상기 유기화합물은, 아래의 화학식을 갖는 것을 특징으로 하는 유기화합물.
Figure 112020131688418-pat00110
As an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of the organic electric element,
The organic compound is an organic compound, characterized in that it has the following chemical formula.
Figure 112020131688418-pat00110
 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물으로서,
상기 유기화합물은, 아래의 화학식을 갖는 것을 특징으로 하는 유기화합물.
Figure 112020131688418-pat00111
As an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of the organic electric element,
The organic compound is an organic compound, characterized in that it has the following chemical formula.
Figure 112020131688418-pat00111
 제 1 항 내지 제 15 항중 어느 한 항에 있어서,
상기 유기화합물은 유기전기소자용 유기박막 재료중 발광층 물질, 정공주입층 물질, 정공수송층 물질, 전자주입층 물질, 전자수송층 물질, 전자차단층 물질 및 정공차단층 물질로 이루어진 군으로부터 선택된 적어도 하나의 용도로 사용되는 것을 특징으로 하는 유기화합물.According to any one of claims 1 to 15,
The organic compound is at least one selected from the group consisting of a light emitting layer material, a hole injection layer material, a hole transport layer material, an electron injection layer material, an electron transport layer material, an electron blocking layer material, and a hole blocking layer material among organic thin film materials for an organic electric device. An organic compound characterized in that it is used for a purpose. 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 잉크 조성물로서,
상기 잉크 조성물은 상기 청구항 1 내지 청구항 15중 선택된 어느 하나의 유기화합물을 포함하는 것을 특징으로 하는 잉크 조성물.An ink composition for forming an organic thin film disposed between a first electrode and a second electrode of an organic electric element,
The ink composition is an ink composition characterized in that it comprises the organic compound of any one selected from claims 1 to 15. 제 17 항에 있어서,
상기 잉크 조성물은 용매를 더 포함하는 용액 또는 현탁액인 것을 특징으로 하는 잉크 조성물.18. The method of claim 17,
The ink composition, characterized in that the ink composition is a solution or suspension further containing a solvent. 제 18 항에 있어서,
상기 잉크 조성물은 안료 또는 염료를 더 포함하는 것을 특징으로 하는 잉크 조성물. According to claim 18,
The ink composition, characterized in that the ink composition further comprises a pigment or dye. 제 18 항에 있어서,
상기 잉크 조성물은 인광 도펀트 또는 형광 도펀트를 더 포함하는 것을 특징으로 하는 잉크 조성물. According to claim 18,
The ink composition further comprises a phosphorescent dopant or a fluorescent dopant. 음극과 양극 사이에 적어도 발광층을 포함하는 일층 또는 복수층으로 이루어지는 유기 박막층이 협지되어 있는 유기전기소자에 있어서,
상기 유기 박막층을 형성하기 위한 유기화합물이 상기 청구항 1 내지 청구항 15중 선택된 어느 하나의 유기화합물을 포함하는 것을 특징으로 하는 유기전기소자. In an organic electric device in which an organic thin film layer comprising one or a plurality of layers including at least a light emitting layer is sandwiched between a cathode and an anode,
An organic electric device characterized in that the organic compound for forming the organic thin film layer includes any one organic compound selected from claims 1 to 15. 제 21 항에 있어서,
상기 유기 박막층을 형성하는 유기화합물의 말단의 벤조시클로부텐기(benzocyclobutene)간에 가교결합이 형성되는 것을 특징으로 하는 유기전기소자. According to claim 21,
An organic electric device, characterized in that a crosslink is formed between benzocyclobutene groups at the ends of organic compounds forming the organic thin film layer. 제 22 항에 있어서,
상기 유기 박막층은 발광층, 정공주입층, 정공수송층, 전자주입층, 전자수송층, 전자차단층 및 정공차단층으로 이루어진 군으로부터 선택된 적어도 하나인 것을 특징으로 하는 유기전기소자.23. The method of claim 22,
The organic electric device, characterized in that the organic thin film layer is at least one selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer and a hole blocking layer. 제 23 항에 있어서,
양극, 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 및 음극이 이 순서대로 적층된 구조를 갖는 것을 특징으로 하는 유기전기소자. 24. The method of claim 23,
An organic electric device characterized in that it has a structure in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and a cathode are stacked in this order. 제 24 항에 있어서,
상기 유기 박막층은 상기 유기화합물을 포함하는 잉크 조성물을 용액 공정에 의해 도포하고 건조시켜 성막하여 제조된 것을 특징으로 하는 유기전기소자. 25. The method of claim 24,
The organic thin film layer is an organic electric device, characterized in that manufactured by coating the ink composition containing the organic compound by a solution process and drying to form a film. 청구항 21에 따른 유기전기소자를 포함하는 전자기기.An electronic device comprising the organic electric element according to claim 21.
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