KR20240003796A - Novel compound and organic electroluminescent device comprising the same - Google Patents

Novel compound and organic electroluminescent device comprising the same Download PDF

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Publication number
KR20240003796A
KR20240003796A KR1020220081438A KR20220081438A KR20240003796A KR 20240003796 A KR20240003796 A KR 20240003796A KR 1020220081438 A KR1020220081438 A KR 1020220081438A KR 20220081438 A KR20220081438 A KR 20220081438A KR 20240003796 A KR20240003796 A KR 20240003796A
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South Korea
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group
formula
substituted
unsubstituted
compound
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KR1020220081438A
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Korean (ko)
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함호완
안현철
김동준
민병철
안자은
권동열
이성규
이지은
이탁재
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주식회사 동진쎄미켐
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Priority to KR1020220081438A priority Critical patent/KR20240003796A/en
Priority to CN202310764969.5A priority patent/CN117362185A/en
Publication of KR20240003796A publication Critical patent/KR20240003796A/en

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Abstract

본 발명은 하기 화학식 1로 표현되는 화합물 및 이를 포함하는 유기 발광 소자를 제공한다.
<화학식 1>
The present invention provides a compound represented by the following formula (1) and an organic light-emitting device containing the same.
<Formula 1>

Description

신규 화합물 및 이를 포함하는 유기 발광 소자{Novel compound and organic electroluminescent device comprising the same} Novel compound and organic electroluminescent device comprising the same}

본 발명은 신규 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다. The present invention relates to novel compounds and organic light-emitting devices containing them.

최근, 자체 발광형으로 저전압 구동이 가능한 유기 발광 소자는, 평판표시소자의 주류인 액정디스플레이(LCD, liquid crystal display)에 비해, 시야각, 대조비 등이 우수하고 백라이트가 불필요하여 경량 및 박형이 가능하며 소비전력 측면에서도 유리하고 색 재현 범위가 넓어, 차세대 표시소자로서 주목을 받고 있다.Recently, organic light-emitting devices that are self-luminous and can be driven at low voltage have superior viewing angles and contrast ratios compared to liquid crystal displays (LCDs), the mainstream flat display devices, and do not require a backlight, making them lightweight and thin. It is attracting attention as a next-generation display device because it is advantageous in terms of power consumption and has a wide color reproduction range.

유기 발광 소자에서 유기물 층으로 사용되는 재료는 크게 기능에 따라, 발광층 재료, 정공주입 재료, 정공수송 재료, 전자수송 재료, 전자주입 재료 등으로 분류될 수 있다. Materials used as organic layers in organic light-emitting devices can be broadly classified into light-emitting layer materials, hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on their function.

그리고 상기 발광 재료는 분자량에 따라 고분자와 단분자로 분류될 수 있고, 발광 메커니즘에 따라 전자의 일중항 여기상태로부터 유래되는 형광 재료, 전자의 삼중항 여기상태로부터 유래되는 인광 재료와 삼중항 여기상태로부터 일중항 여기상태로 전자의 이동이 유래 되는 지연형광 재료로 분류될 수 있으며, 발광 재료는 발광색에 따라 청색, 녹색, 적색 발광 재료와 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 재료로 구분될 수 있다. In addition, the light-emitting materials can be classified into polymers and single molecules depending on their molecular weight, and depending on the light-emitting mechanism, fluorescent materials derived from a singlet excited state of electrons, phosphorescent materials derived from a triplet excited state of electrons, and triplet excited states. It can be classified into delayed fluorescent materials, which are derived from the movement of electrons from a singlet excited state. Depending on the emission color, light-emitting materials are divided into blue, green, and red light-emitting materials, and yellow and orange light-emitting materials necessary to realize better natural colors. It can be.

또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 물질로서 호스트/도판트 계를 사용할 수 있다. 그 원리는 호스트보다 에너지 대역 간극이 작고 발광물질인 도판트를 발광층에 소량 혼합하면, 호스트에서 생성된 엑시톤이 도판트로 전이되어 빛을 내는 것이다. 이러한 원리를 이용하여 도판트와 호스트의 종류에 따라 원하는 파장의 빛을 얻을 수 있다. Additionally, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system can be used as a luminescent material. The principle is that when a small amount of dopant, which is a light-emitting material and has a smaller energy band gap than the host, is mixed into the light-emitting layer, the exciton generated in the host is transferred to the dopant and emits light. Using this principle, light of the desired wavelength can be obtained depending on the type of dopant and host.

현재까지 이러한 유기 발광 소자에 사용되는 물질로서 다양한 화합물들이 알려져 있으나, 이제까지 알려진 물질을 이용한 유기 발광 소자의 경우 높은 구동전압, 낮은 효율 및 짧은 수명으로 인해 새로운 재료의 개발이 지속적으로 요구되고 있다. 따라서, 우수한 특성을 갖는 물질을 이용하여 저전압 구동, 고휘도 및 장수명을 갖는 유기 발광 소자를 개발하려는 노력이 지속되어 왔다.To date, various compounds are known as materials used in such organic light-emitting devices, but in the case of organic light-emitting devices using known materials, the development of new materials is continuously required due to high driving voltage, low efficiency, and short lifespan. Accordingly, efforts have been made to develop organic light-emitting devices with low-voltage operation, high brightness, and long lifespan using materials with excellent properties.

본 발명은 축합사이클릭기를 포함하는 아릴아민 화합물로서 정공수공에 적합한 HOMO 형성 및 높은 LUMO를 유지할 수 있는 아릴아민 화합물을 제공하는 것을 목적으로 한다.The purpose of the present invention is to provide an arylamine compound containing a condensed cyclic group, which is capable of forming a HOMO suitable for hole vacancy and maintaining a high LUMO.

또한, 빠른 홀모빌리티를 가짐과 동시에 전자차단이 용이하여, 낮은 구동전압, 고효율 및 롤오프 현상 억제를 통한 장수명 효과를 구현할 수 있는 신규 화합물 및 유기 발광 소자를 제공하는 것을 목적으로 한다.In addition, the purpose is to provide new compounds and organic light-emitting devices that have fast hole mobility and are easy to block electrons, thereby realizing long life effects through low driving voltage, high efficiency, and suppression of roll-off phenomenon.

또한, 벌키 모이어티와 축합사이클릭기 도입으로 낮은 굴절률을 가짐으로써 발광층 내측에서 외부로 광추출 효과를 높일 수 있어, 효율 개선에 더욱 효과적인 신규 화합물 및 유기 발광 소자를 제공하는 것을 목적으로 한다.In addition, the purpose is to provide new compounds and organic light-emitting devices that are more effective in improving efficiency by having a low refractive index by introducing bulky moieties and condensed cyclic groups, which can increase the light extraction effect from the inside of the light-emitting layer to the outside.

또한, 축합사이클릭기 도입은 높은 Tg를 가져 열안정성이 우수하며, 박막의 재결정화 방지를 통한 구동 안정성이 뛰어난 신규 화합물 및 유기 발광 소자를 제공하는 것을 목적으로 한다.In addition, the purpose of introducing a condensed cyclic group is to provide a new compound and organic light-emitting device that has a high Tg, has excellent thermal stability, and has excellent driving stability by preventing recrystallization of the thin film.

상기의 과제 및 추가적 과제에 대하여 아래에서 자세히 서술한다.The above tasks and additional tasks are described in detail below.

상기 과제를 해결하기 위한 수단으로서,As a means to solve the above problems,

본 발명은 일실시예로서, 하기 화학식 1로 표현되는 화합물을 제공한다.As an example, the present invention provides a compound represented by the following formula (1).

<화학식 1><Formula 1>

<화학식 1-1><Formula 1-1>

상기 화학식 1에서, In Formula 1,

X는 C, Si, Ge, Sn 또는 Pb이며,X is C, Si, Ge, Sn or Pb,

ArCy는 상기 [화학식1-1]로 표시되는 축합환기이며,ArCy is a condensed ring group represented by [Formula 1-1] above,

Ar은 치환 또는 비치환된 C3~C50의 아릴기, 또는 치환 또는 비치환된 C2~C50의 헤테로아릴기이며,Ar is a substituted or unsubstituted C3~C50 aryl group, or a substituted or unsubstituted C2~C50 heteroaryl group,

Cy는 치환 또는 비치환된 C1~C50의 사이클로알킬기, 또는 C0~C50의 헤테로사이클릭기이고,Cy is a substituted or unsubstituted C1~C50 cycloalkyl group, or a C0~C50 heterocyclic group,

Ar1 및 Ar2는 각각 독립적으로 치환 또는 비치환된 C3~C50의 아릴기, 치환 또는 비치환된 C2~C50의 헤테로아릴기, 또는 상기 [화학식1-1]이고,Ar1 and Ar2 are each independently a substituted or unsubstituted C3 to C50 aryl group, a substituted or unsubstituted C2 to C50 heteroaryl group, or the above [Formula 1-1],

L1 내지 L3는 각각 독립적으로 직접결합, 치환 또는 비치환된 C3~C50의 아릴렌기, 치환 또는 비치환된 C2~C50의 헤테로아릴렌기이고,L1 to L3 are each independently a direct bond, a substituted or unsubstituted C3 to C50 arylene group, or a substituted or unsubstituted C2 to C50 heteroarylene group,

R1 및 R2는 각각 독립적으로 수소, 중수소, 할로겐, 니트로기, 니트릴기, 하이드록시기, 티올기, 치환 또는 비치환된 아미노기, 치환 또는 비치환된 C1~C50의 알킬기, 치환 또는 비치환된 C2~C50의 알케닐기, 치환 또는 비치환된 C1~C50의 알콕시기, 치환 또는 비치환된 C1~C50의 설파이드기, 치환 또는 비치환된 C0~C50의 실릴기, 치환 또는 비치환된 C3~C50의 사이클로알킬기, 치환 또는 비치환된 C3~C50의 사이클로알케닐기, 치환 또는 비치환된 C1~C50의 헤테로사이클릴기, 치환 또는 비치환된 C3~C50의 아릴기, 또는 치환 또는 비치환된 C2~C50의 헤테로아릴기이다.R1 and R2 are each independently hydrogen, deuterium, halogen, nitro group, nitrile group, hydroxy group, thiol group, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C50 alkyl group, substituted or unsubstituted C2 ~C50 alkenyl group, substituted or unsubstituted C1~C50 alkoxy group, substituted or unsubstituted C1~C50 sulfide group, substituted or unsubstituted C0~C50 silyl group, substituted or unsubstituted C3~C50 cycloalkyl group, substituted or unsubstituted C3~C50 cycloalkenyl group, substituted or unsubstituted C1~C50 heterocyclyl group, substituted or unsubstituted C3~C50 aryl group, or substituted or unsubstituted C2~ It is a heteroaryl group of C50.

본 발명은 또한, 상기 화합물을 포함하는 유기 발광 소자를 제공한다.The present invention also provides an organic light-emitting device containing the above compound.

본 발명에 따른 화합물은 축합사이클릭기를 포함하는 아릴아민 화합물로서 정공수공에 적합한 HOMO 형성 및 높은 LUMO를 유지할 수 있다.The compound according to the present invention is an arylamine compound containing a condensed cyclic group, and can form HOMO suitable for hole vacancy and maintain high LUMO.

또한, 본 발명에 따른 화합물은 빠른 홀모빌리티를 가짐과 동시에 전자차단이 용이하여, 낮은 구동전압, 고효율 및 롤오프 현상 억제를 통한 장수명 효과를 가지는 유기 발광 소자를 구현할 수 있다.In addition, the compound according to the present invention has fast hole mobility and is easy to block electrons, making it possible to implement an organic light-emitting device with low driving voltage, high efficiency, and long lifespan by suppressing the roll-off phenomenon.

또한, 본 발명에 따른 화합물은 벌키 모이어티와 축합사이클릭기 도입으로 낮은 굴절률을 가짐으로써 발광층 내측에서 외부로 광추출 효과를 높일 수 있어, 효율 개선에 더욱 효과적이다.In addition, the compound according to the present invention has a low refractive index by introducing a bulky moiety and a condensed cyclic group, thereby increasing the light extraction effect from the inside of the emitting layer to the outside, making it more effective in improving efficiency.

또한, 본 발명에 따른 화합물은 축합사이클릭기 도입으로 높은 Tg를 가져 열안정성이 우수하며, 박막의 재결정화 방지를 통한 구동 안정성이 뛰어난 유기 발광 소자를 구현할 수 있다.In addition, the compound according to the present invention has a high Tg due to the introduction of a condensation cyclic group, has excellent thermal stability, and can implement an organic light-emitting device with excellent driving stability by preventing recrystallization of the thin film.

상기의 효과 및 추가적 효과에 대하여 아래에서 자세히 서술한다.The above effects and additional effects are described in detail below.

도 1은 본 발명의 일 실시예에 따른 유기 발광 소자의 구성 개략 단면도이다. 1 is a schematic cross-sectional view of the structure of an organic light-emitting device according to an embodiment of the present invention.

이하에 본 발명을 상세하게 설명하기에 앞서, 본 명세서에 사용된 용어는 특정의 실시예를 기술하기 위한 것일 뿐 첨부하는 특허청구의 범위에 의해서만 한정되는 본 발명의 범위를 한정하려는 것은 아님을 이해하여야 한다. 본 명세서에 사용되는 모든 기술용어 및 과학용어는 다른 언급이 없는 한은 기술적으로 통상의 기술을 가진 자에게 일반적으로 이해되는 것과 동일한 의미를 가진다.Before describing the present invention in detail below, it is understood that the terms used in this specification are only for describing specific embodiments and are not intended to limit the scope of the present invention, which is limited only by the scope of the appended claims. shall. All technical and scientific terms used in this specification have the same meaning as generally understood by those skilled in the art, unless otherwise specified.

본 명세서 및 청구범위의 전반에 걸쳐, 다른 언급이 없는 한 포함(comprise, comprises, comprising)이라는 용어는 언급된 물건, 단계 또는 일군의 물건, 및 단계를 포함하는 것을 의미하고, 임의의 어떤 다른 물건, 단계 또는 일군의 물건 또는 일군의 단계를 배제하는 의미로 사용된 것은 아니다.Throughout this specification and claims, unless otherwise stated, the terms comprise, comprises, and comprise mean to include the mentioned article, step, or group of articles, and steps, and any other article. , it is not used in the sense of excluding a step, a group of objects, or a group of steps.

본 명세서 및 청구범위의 전반에 걸쳐, 용어 "아릴"은 C5-50의 방향족 탄화수소 고리기, 예를 들어, 페닐, 벤질, 나프틸, 비페닐, 터페닐, 플루오렌, 페난트레닐, 트리페닐레닐, 페릴레닐, 크리세닐, 플루오란테닐, 벤조플루오레닐, 벤조트리페닐레닐, 벤조크리세닐, 안트라세닐, 스틸베닐, 파이레닐 등의 방향족 고리를 포함하는 것을 의미하며, "헤테로아릴"은 적어도 1 개의 헤테로 원소를 포함하는 C2-50의 방향족 고리로서, 예를 들어, 피롤릴, 피라지닐, 피리디닐, 인돌릴, 이소인돌릴, 푸릴, 벤조푸라닐, 이소벤조푸라닐, 디벤조푸라닐, 벤조티오페닐, 디벤조티오페닐, 퀴놀릴, 이소퀴놀릴, 퀴녹살리닐, 카르바졸릴, 페난트리디닐, 아크리디닐, 페난트롤리닐, 티에닐, 및 피리딘 고리, 피라진 고리, 피리미딘 고리, 피리다진 고리, 트리아진 고리, 인돌 고리, 퀴놀린 고리, 아크리딘 고리, 피롤리딘 고리, 디옥산 고리, 피페리딘 고리, 모르폴린 고리, 피페라진 고리, 카르바졸 고리, 푸란 고리, 티오펜 고리, 옥사졸 고리, 옥사디아졸 고리, 벤조퓨란 고리, 티아졸 고리, 티아디아졸 고리, 벤조티오펜 고리, 트리아졸 고리, 이미다졸 고리, 벤조이미다졸 고리, 피란 고리, 디벤조푸란 고리 등으로부터 형성되는 헤테로고리기를 포함하는 것을 의미할 수 있다.Throughout this specification and claims, the term “aryl” refers to a C5-50 aromatic hydrocarbon ring group, such as phenyl, benzyl, naphthyl, biphenyl, terphenyl, fluorene, phenanthrenyl, triphenyl. “Heteroaryl” refers to containing aromatic rings such as renyl, perylenyl, chrysenyl, fluoranthenyl, benzofluorenyl, benzotriphenylenyl, benzochrysenyl, anthracenyl, stilbenyl, and pyrenyl. is a C2-50 aromatic ring containing at least one hetero atom, for example, pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindolyl, furyl, benzofuranyl, isobenzofuranyl, dibenzo furanyl, benzothiophenyl, dibenzothiophenyl, quinolyl, isoquinolyl, quinoxalinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, thienyl, and pyridine rings, pyrazine rings, pyridine rings. Midine ring, pyridazine ring, triazine ring, indole ring, quinoline ring, acridine ring, pyrrolidine ring, dioxane ring, piperidine ring, morpholine ring, piperazine ring, carbazole ring, furan ring. , thiophene ring, oxazole ring, oxadiazole ring, benzofuran ring, thiazole ring, thiadiazole ring, benzothiophene ring, triazole ring, imidazole ring, benzoimidazole ring, pyran ring, dibenzo It may mean including a heterocyclic group formed from a furan ring, etc.

또한, 화학식에서 Arx(여기서 x는 정수임)는 특별히 정의되지 않는 경우, 치환 또는 비치환된 C6~C50의 아릴기, 또는 치환 또는 비치환된 C2~C50의 헤테로아릴기를 의미하며, L x(여기서 x는 정수임)은 특별히 정의되지 않는 경우, 직접결합, 치환 또는 비치환된 C6~C50의 아릴렌기, 또는 치환 또는 비치환된 C2~C50의 헤테로아릴렌기를 의미하며, Rx(여기서 x는 정수임)은 특별히 정의되지 않는 경우, 수소, 중수소, 할로겐, 니트로기, 니트릴기, 치환 또는 비치환된 C1~C30의 알킬기, 치환 또는 비치환된 C2~C30의 알케닐기, 치환 또는 비치환된 C1~C30의 알콕시기, 치환 또는 비치환된 C1~C30의 설파이드기, 치환 또는 비치환된 C6~C50의 아릴기, 또는 치환 또는 비치환된 C2~C50의 헤테로아릴기를 의미한다.In addition, in the chemical formula, Ar where x is an integer), unless specifically defined, means a direct bond, a substituted or unsubstituted C6~C50 arylene group, or a substituted or unsubstituted C2~C50 heteroarylene group, and R x (where x is (is an integer), unless specifically defined, refers to hydrogen, deuterium, halogen, nitro group, nitrile group, substituted or unsubstituted C1~C30 alkyl group, substituted or unsubstituted C2~C30 alkenyl group, substituted or unsubstituted C1 It means a ~C30 alkoxy group, a substituted or unsubstituted C1~C30 sulfide group, a substituted or unsubstituted C6~C50 aryl group, or a substituted or unsubstituted C2~C50 heteroaryl group.

본 명세서 및 청구범위 전반에 걸쳐, 용어 "치환 또는 비치환된"은 중수소, 할로겐, 아미노기, 시아노기, 니트릴기, 니트로기, 니트로소기, 술파모일기, 이소티오시아네이트기, 티오시아네이트기, 카르복시기, 카르보닐기, 또는 C1~C30의 알킬기, C1~C30의 알킬술피닐기, C1~C30의 알킬술포닐기, C1~C30의 알킬술파닐기, C1∼C12의 플루오로알킬기, C2~C30의 알케닐기, C1~C30의 알콕시기, C1~C12의 N-알킬아미노기, C2~C20의 N,N-디알킬아미노기, 치환 또는 비치환된 C1~C30의 설파이드기, C1∼C6의 N-알킬술파모일기, C2∼C12의 N,N-디알킬술파모일기, C0~C30의 실릴기, C3~C20의 시클로알킬기, C3~C20의 헤테로시클로알킬기, C6~C50의 아릴기 및 C3~C50의 헤테로아릴기 등으로 이루어진 군으로부터 선택된 하나 이상의 기로 치환되거나 치환되지 않는 것을 의미할 수 있다. 또한, 본원 명세서 전체에서 동일한 기호는 특별히 언급하지 않는 한 같은 의미를 가질 수 있다.Throughout this specification and claims, the term "substituted or unsubstituted" refers to deuterium, halogen, amino group, cyano group, nitrile group, nitro group, nitroso group, sulfamoyl group, isothiocyanate group, thiocyanate group. , carboxyl group, carbonyl group, or C1 to C30 alkyl group, C1 to C30 alkylsulfinyl group, C1 to C30 alkylsulfonyl group, C1 to C30 alkylsulfanyl group, C1 to C12 fluoroalkyl group, C2 to C30 alkenyl group. , C1~C30 alkoxy group, C1~C12 N-alkylamino group, C2~C20 N,N-dialkylamino group, substituted or unsubstituted C1~C30 sulfide group, C1~C6 N-alkyl sulfamo. Dial group, C2 to C12 N,N-dialkylsulfamoyl group, C0 to C30 silyl group, C3 to C20 cycloalkyl group, C3 to C20 heterocycloalkyl group, C6 to C50 aryl group and C3 to C50 hetero It may mean that it is substituted or unsubstituted with one or more groups selected from the group consisting of aryl groups, etc. Additionally, the same symbols throughout the specification may have the same meaning unless otherwise specified.

한편, 본 발명의 여러 가지 실시예들은 명확한 반대의 지적이 없는 한 그 외의 어떤 다른 실시예들과 결합될 수 있다. 이하, 본 발명의 실시예 및 이에 따른 효과를 설명하기로 한다.Meanwhile, various embodiments of the present invention may be combined with any other embodiments unless clearly indicated to the contrary. Hereinafter, embodiments of the present invention and effects thereof will be described.

본 발명에 따른 화합물은 하기 화학식 1로 표현된다. The compound according to the present invention is represented by the following formula (1).

<화학식 1><Formula 1>

<화학식 1-1><Formula 1-1>

상기 화학식 1에서, In Formula 1,

X는 C, Si, Ge, Sn 또는 Pb이며,X is C, Si, Ge, Sn or Pb,

ArCy는 상기 [화학식1-1]로 표시되는 축합환기이며,ArCy is a condensed ring group represented by [Formula 1-1] above,

Ar은 치환 또는 비치환된 C3~C50의 아릴기, 또는 치환 또는 비치환된 C2~C50의 헤테로아릴기이며,Ar is a substituted or unsubstituted C3~C50 aryl group, or a substituted or unsubstituted C2~C50 heteroaryl group,

Cy는 치환 또는 비치환된 C1~C50의 사이클로알킬기, 또는 C0~C50의 헤테로사이클릭기이고,Cy is a substituted or unsubstituted C1~C50 cycloalkyl group, or a C0~C50 heterocyclic group,

Ar1 및 Ar2는 각각 독립적으로 치환 또는 비치환된 C3~C50의 아릴기, 치환 또는 비치환된 C2~C50의 헤테로아릴기, 또는 상기 [화학식1-1]이고,Ar1 and Ar2 are each independently a substituted or unsubstituted C3 to C50 aryl group, a substituted or unsubstituted C2 to C50 heteroaryl group, or the above [Formula 1-1],

L1 내지 L3는 각각 독립적으로 직접결합, 치환 또는 비치환된 C3~C50의 아릴렌기, 치환 또는 비치환된 C2~C50의 헤테로아릴렌기이고,L1 to L3 are each independently a direct bond, a substituted or unsubstituted C3 to C50 arylene group, or a substituted or unsubstituted C2 to C50 heteroarylene group,

R1 및 R2는 각각 독립적으로 수소, 중수소, 할로겐, 니트로기, 니트릴기, 하이드록시기, 티올기, 치환 또는 비치환된 아미노기, 치환 또는 비치환된 C1~C50의 알킬기, 치환 또는 비치환된 C2~C50의 알케닐기, 치환 또는 비치환된 C1~C50의 알콕시기, 치환 또는 비치환된 C1~C50의 설파이드기, 치환 또는 비치환된 C0~C50의 실릴기, 치환 또는 비치환된 C3~C50의 사이클로알킬기, 치환 또는 비치환된 C3~C50의 사이클로알케닐기, 치환 또는 비치환된 C1~C50의 헤테로사이클릴기, 치환 또는 비치환된 C3~C50의 아릴기, 또는 치환 또는 비치환된 C2~C50의 헤테로아릴기이다.R1 and R2 are each independently hydrogen, deuterium, halogen, nitro group, nitrile group, hydroxy group, thiol group, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C50 alkyl group, substituted or unsubstituted C2 ~C50 alkenyl group, substituted or unsubstituted C1~C50 alkoxy group, substituted or unsubstituted C1~C50 sulfide group, substituted or unsubstituted C0~C50 silyl group, substituted or unsubstituted C3~C50 cycloalkyl group, substituted or unsubstituted C3~C50 cycloalkenyl group, substituted or unsubstituted C1~C50 heterocyclyl group, substituted or unsubstituted C3~C50 aryl group, or substituted or unsubstituted C2~ It is a heteroaryl group of C50.

상기에서, 치환되는 경우 치환기는 중수소, 할로겐, 아미노기, 시아노기, 니트릴기, 니트로기, 니트로소기, 술파모일기, 이소티오시아네이트기, 티오시아네이트기, 카르복시기, 카르보닐기, 또는 C1~C30의 알킬기, C1~C30의 알킬술피닐기, C1~C30의 알킬술포닐기, C1~C30의 알킬술파닐기, C1∼C12의 플루오로알킬기, C2~C30의 알케닐기, C1~C30의 알콕시기, C1~C12의 N-알킬아미노기, C2~C20의 N,N-디알킬아미노기, 치환 또는 비치환된 C1~C30의 설파이드기, C1∼C6의 N-알킬술파모일기, C2∼C12의 N,N-디알킬술파모일기, C0~C30의 실릴기, C3~C20의 시클로알킬기, C3~C20의 헤테로시클로알킬기, C6~C50의 아릴기 및 C3~C50의 헤테로아릴기 등으로 이루어진 군으로부터 선택된 하나 이상의 기일 수 있다.In the above, when substituted, the substituent is deuterium, halogen, amino group, cyano group, nitrile group, nitro group, nitroso group, sulfamoyl group, isothiocyanate group, thiocyanate group, carboxyl group, carbonyl group, or C1 to C30. Alkyl group, C1~C30 alkylsulfinyl group, C1~C30 alkylsulfonyl group, C1~C30 alkylsulfanyl group, C1~C12 fluoroalkyl group, C2~C30 alkenyl group, C1~C30 alkoxy group, C1~ C12 N-alkylamino group, C2~C20 N,N-dialkylamino group, substituted or unsubstituted C1~C30 sulfide group, C1~C6 N-alkylsulfamoyl group, C2~C12 N,N- At least one selected from the group consisting of dialkyl sulfamoyl group, C0~C30 silyl group, C3~C20 cycloalkyl group, C3~C20 heterocycloalkyl group, C6~C50 aryl group, and C3~C50 heteroaryl group. It could be a sign.

상기와 같이 화학식 1로 표현되는 본 발명의 화합물은 축합사이클릭기를 포함하는 아릴아민 화합물로서 정공수공에 적합한 HOMO 형성 및 높은 LUMO를 유지할 수 있어 빠른 홀모빌리티를 가짐과 동시에 전자차단이 용이하여, 낮은 구동전압, 고효율 및 롤오프 현상 억제를 통한 장수명 효과를 가지는 유기 발광 소자를 구현할 수 있다. 또한, 벌키 모이어티와 축합사이클릭기 도입으로 낮은 굴절률을 가짐으로써 발광층 내측에서 외부로 광추출 효과를 높일 수 있어, 효율 개선에 더욱 효과적이다. 또한, 축합사이클릭기 도입으로 높은 Tg를 가져 열안정성이 우수하며, 박막의 재결정화 방지를 통한 구동 안정성이 뛰어난 유기 발광 소자를 구현할 수 있다.As described above, the compound of the present invention represented by Formula 1 is an arylamine compound containing a condensed cyclic group, and is capable of forming a HOMO suitable for hole vacancy and maintaining a high LUMO, so it has fast hole mobility and is easy to block electrons, resulting in low It is possible to implement an organic light emitting device that has a long lifespan effect through low driving voltage, high efficiency, and suppression of roll-off phenomenon. In addition, by having a low refractive index by introducing a bulky moiety and a condensed cyclic group, the light extraction effect from the inside of the light emitting layer to the outside can be increased, making it more effective in improving efficiency. In addition, by introducing a condensation cyclic group, it is possible to implement an organic light-emitting device that has a high Tg, has excellent thermal stability, and has excellent driving stability by preventing recrystallization of the thin film.

더 구체적으로는, 상기 화학식 1은 하기 화학식 2로 표현될 수 있다.More specifically, Formula 1 may be expressed as Formula 2 below.

<화학식 2><Formula 2>

상기 화학식 2에서, In Formula 2,

상기 화학식 1과 동일한 기호는 화학식 1에서의 정의와 동일하며,Symbols identical to those in Formula 1 are the same as those defined in Formula 1,

R3는 상기 R1 및 R2의 정의와 동일하며, 인접한 R3끼리 연결되어 환을 형성할 수도 있으며,R3 is the same as the definition of R1 and R2 above, and adjacent R3s may be connected to form a ring,

l은 0 내지 3의 정수이다.l is an integer from 0 to 3.

상기 화학식 2의 화합물은 축합환기의 파이컨쥬게이션을 최소화하여 높은 LUMO와 T1을 유지할 수 있어, 엑시톤 차단에 효과적이므로 효율 개선에 효과적일 수 있다.The compound of Formula 2 can maintain high LUMO and T1 by minimizing pi-conjugation of condensed ring groups, and is effective in blocking exciton, so it can be effective in improving efficiency.

또한, 상기 화학식 1은 구체적으로 하기 화학식 3으로 표현될 수 있다. Additionally, Chemical Formula 1 may be specifically expressed as Chemical Formula 3 below.

<화학식 3><Formula 3>

상기 화학식 3에서, In Formula 3 above,

상기 화학식 1과 동일한 기호는 화학식 1에서의 정의와 동일하며,Symbols identical to those in Formula 1 are the same as those defined in Formula 1,

Z는 각각 독립적으로 CRR`, O, S, NR, SiRR` 또는 GeRR`이며,Z is each independently CRR`, O, S, NR, SiRR` or GeRR`,

R3, R 및 R'는 각각 독립적으로 상기 R1 및 R2의 정의와 동일하며, R3, R 및 R’ 중 2개 이상이 연결되어 환을 형성할 수도 있으며,R3, R and R' are each independently the same as the definitions of R1 and R2 above, and two or more of R3, R and R' may be connected to form a ring,

l은 0 내지 3의 정수이며,l is an integer from 0 to 3,

m는 1 내지 5의 정수이다.m is an integer from 1 to 5.

상기 화학식 3의 화합물은 Cy이 구조가 특정 구조로 이루어져 높은 HOMO를 형성할 수 있음과 동시에 높은 LUMO와 T1을 유지하여, 더욱이 효율 개선에 효과적이다.The compound of Formula 3 has a specific Cy structure and can form high HOMO while maintaining high LUMO and T1, which is further effective in improving efficiency.

또한, 상기 화학식 1은 구체적으로 하기 화학식 4로 표현될 수 있다. Additionally, Chemical Formula 1 may be specifically expressed as Chemical Formula 4 below.

<화학식 4><Formula 4>

상기 화학식 4에서,In Formula 4 above,

상기 화학식 1과 동일한 기호는 화학식 1에서의 정의와 동일하며,Symbols identical to those in Formula 1 are the same as those defined in Formula 1,

Z는 각각 독립적으로 CRR`, O, S, NR, SiRR` 또는 GeRR`이며,Z is each independently CRR`, O, S, NR, SiRR` or GeRR`,

R3, R4, R 및 R'는 각각 독립적으로 상기 R1 및 R2의 정의와 동일하며, R3, R 및 R’ 중 2개 이상이 연결되어 환을 형성할 수도 있으며, R4, R 및 R’ 중 2개 이상이 연결되어 환을 형성할 수도 있으며,R3, R4, R and R' are each independently the same as the definitions of R1 and R2 above, and two or more of R3, R and R' may be connected to form a ring, and two of R4, R and R' may be connected. More than one may be connected to form a ring,

l은 각각 독립적으로 0 내지 3의 정수이며,l is each independently an integer from 0 to 3,

m 및 n은 각각 독립적으로 1 내지 5의 정수이다.m and n are each independently integers from 1 to 5.

상기 화학식 4의 화합물은 축합환기를 추가로 가짐으로써, 높은 HOMO를 형성할 수 있고 빠른 홀 모빌리티를 가지며, 동시에 낮은 굴절률을 가질 수 있어, 더욱이 구동전압 개선에 효과적이다.By additionally having a condensed ring group, the compound of Formula 4 can form a high HOMO, have fast hole mobility, and at the same time have a low refractive index, making it effective in improving driving voltage.

또한, 상기 화학식 1 내지 화학식 4에서, 상기 ArCy 또는 이에 해당하는 구조가 하기 화학식 1-2 또는 화학식1-3으로 표현되는 화합물일 수 있다. 축합기의 벌키특성을 최소화하여, 빠른 홀 모빌리티를 가지며, 낮은 굴절률을 가져, 구동 및 효율 개선에 효과적이고 동시에 증착온도 개선에 효과적이다. Additionally, in Formulas 1 to 4, the ArCy or the corresponding structure may be a compound represented by the following Formula 1-2 or Formula 1-3. By minimizing the bulky characteristics of the condenser, it has fast hole mobility and a low refractive index, which is effective in improving drive and efficiency and at the same time is effective in improving deposition temperature.

<화학식 1-2><Formula 1-2>

<화학식 1-3><Formula 1-3>

상기 화학식 1-2 및 화학식 1-3에서,In Formula 1-2 and Formula 1-3,

상기 Z는 각각 독립적으로 CRR`, O, S, NR 또는 SiRR`이며,The Z is each independently CRR`, O, S, NR or SiRR`,

R 및 R'는 각각 독립적으로 상기 화학식 1의 R1 및 R2의 정의와 동일하며, R 및 R’ 중 2개 이상이 연결되어 환을 형성할 수도 있다.R and R' are each independently the same as the definitions of R1 and R2 in Formula 1 above, and two or more of R and R' may be connected to form a ring.

또한, 상기 화학식 1 내지 화학식 4에서, 상기 Ar1, R1 및 R2는 각각 독립적으로 페닐기, 비페닐기 또는 나프틸기일 수 있다. 이를 통해 벌키특성이 최소화되어 박막배열이 우수하고 빠른 홀모빌리티를 유지할 수 있어, 롤오프현상 억제와 동시에 열안정성 및 증착온도 개선에 효과적이다.Additionally, in Formulas 1 to 4, Ar1, R1, and R2 may each independently be a phenyl group, a biphenyl group, or a naphthyl group. Through this, bulk characteristics are minimized, allowing excellent thin film arrangement and maintaining fast hole mobility, which is effective in suppressing roll-off phenomenon and improving thermal stability and deposition temperature.

또한, 상기 화학식 1 내지 화학식 4에서, 상기 L1은 페닐렌, 비페닐렌, 터페닐렌 및 이들의 조합일 수 있다. 이를 통해 연결기의 파이컨쥬게이션이 증가되어 빠른 홀모볼리티를 가질 수 있고 높은 T1을 유지 할 수 있어, 구동전압 및 효율 개선에 효과적이다.Additionally, in Formulas 1 to 4, L1 may be phenylene, biphenylene, terphenylene, or a combination thereof. Through this, the pi-conjugation of the connector increases, enabling fast homovolity and maintaining high T1, which is effective in improving driving voltage and efficiency.

또한, 상기 화학식 1 내지 화학식 4에서, 상기 L1 내지 L3중 하나 이상은 메타페닐렌 또는 오쏘페닐렌을 포함할 수 있다. 이를 통해 높은 LUMO 및 T1을 형성하고, 동시에 낮은 굴절률을 가질 수 있어, 효율 개선에 효과적이다.Additionally, in Formulas 1 to 4, one or more of L1 to L3 may include metaphenylene or orthophenylene. Through this, it is possible to form high LUMO and T1 and have a low refractive index at the same time, which is effective in improving efficiency.

또한, 상기 화학식 1 내지 화학식 4에서 상기 L2는 C3~C12의 아릴렌기 또는 C2~C12의 헤테로아릴렌기일 수 있고, 구체적으로는 페닐렌기일 수 있다.Additionally, in Formulas 1 to 4, L2 may be a C3 to C12 arylene group or a C2 to C12 heteroarylene group, and specifically, may be a phenylene group.

또한, 상기 화학식 1 내지 화학식 4에서, 상기 L2는 직접결합일 수 있다. 더욱 높은 HOMO를 형성할 수 있어, 정공주입이 원활하고 동시에 낮은 굴절률을 가질 수 있어, 구동전압 개선 및 효율 개선에 효과적이다.Additionally, in Formulas 1 to 4, L2 may be a direct bond. It can form a higher HOMO, allowing for smooth hole injection and at the same time having a low refractive index, which is effective in improving driving voltage and efficiency.

또한, 상기 화학식 1 내지 화학식 4에서, 상기 R 및 R'는 치환 또는 비치환된 C1~C50의 알킬기일 수 있다. 이를 통해 전자주개 특성이 강화되어 더욱이 빠른 모빌리티를 가짐과 동시에 열안정성 개선에 효과적이다.Additionally, in Formulas 1 to 4, R and R' may be substituted or unsubstituted C1-C50 alkyl groups. Through this, the electron donor characteristics are strengthened, enabling faster mobility and at the same time being effective in improving thermal stability.

또한, 상기 화학식 1 내지 화학식 3에서, 상기 Ar1은 페닐, 비페닐, 터페닐, 나프틸, 페난트렌, 트리페닐렌, 디메틸플루오렌, 디페닐플루오렌, 스파이로비플루오렌, 디벤조퓨란, 디벤조티오펜, 카바졸, 상기 <화학식1-1> 및 이들의 조합으로 이루어진 군에서 선택될 수 있다. 이를 통해 빠른 모빌리티를 유지하며, 높은 LUMO 및 T1을 형성하고 열안정성이 우수하여, 효율 및 수명 개선에 효과적이다.In addition, in Formulas 1 to 3, Ar1 is phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, triphenylene, dimethyl fluorene, diphenyl fluorene, spirobifluorene, dibenzofuran, di It may be selected from the group consisting of benzothiophene, carbazole, <Formula 1-1>, and combinations thereof. Through this, it maintains fast mobility, forms high LUMO and T1, and has excellent thermal stability, which is effective in improving efficiency and lifespan.

또한, 상기 <화학식1-1>은 하기 화학 구조식 A-1 내지 A-35 중에서 선택될 수 있다.Additionally, <Formula 1-1> may be selected from the following chemical structures A-1 to A-35.

상기 화학 구조식에서, R8은 각각 독립적으로 수소, 중수소, 할로겐, 니트로기, 니트릴기, 하이드록시기, 티올기, 치환 또는 비치환된 아미노기, 치환 또는 비치환된 C1~C50의 알킬기, 치환 또는 비치환된 C2~C50의 알케닐기, 치환 또는 비치환된 C1~C50의 알콕시기, 치환 또는 비치환된 C1~C50의 설파이드기, 치환 또는 비치환된 C0~C50의 실릴기, 치환 또는 비치환된 C3~C50의 사이클로알킬기, 치환 또는 비치환된 C3~C50의 사이클로알케닐기, 치환 또는 비치환된 C1~C50의 헤테로사이클릴기, 치환 또는 비치환된 C3~C50의 아릴기, 또는 치환 또는 비치환된 C2~C50의 헤테로아릴기이며,In the above chemical structural formula, R8 is each independently hydrogen, deuterium, halogen, nitro group, nitrile group, hydroxy group, thiol group, substituted or unsubstituted amino group, substituted or unsubstituted alkyl group of C1 to C50, substituted or unsubstituted. Substituted C2~C50 alkenyl group, substituted or unsubstituted C1~C50 alkoxy group, substituted or unsubstituted C1~C50 sulfide group, substituted or unsubstituted C0~C50 silyl group, substituted or unsubstituted C3~C50 cycloalkyl group, substituted or unsubstituted C3~C50 cycloalkenyl group, substituted or unsubstituted C1~C50 heterocyclyl group, substituted or unsubstituted C3~C50 aryl group, or substituted or unsubstituted It is a heteroaryl group from C2 to C50,

u는 각각 독립적으로 구조적으로 허용되는 범위내에서 0 내지 10의 정수이고, 구체적으로 0 내지 4의 정수이며,u is each independently an integer from 0 to 10 within a structurally acceptable range, and specifically an integer from 0 to 4,

*는 결합위치를 나타낸다.* indicates the binding position.

한편, 상기 화학식 1의 화합물의 굴절률은 450nm 파장에서 1.70이하일 수 있다. 낮은 굴절률을 가짐으로써 발광층 내측에서 외부로 광추출 효과를 높일 수 있어 효율 개선에 더욱 효과적이다.Meanwhile, the refractive index of the compound of Formula 1 may be 1.70 or less at a wavelength of 450 nm. By having a low refractive index, the light extraction effect can be increased from the inside of the light emitting layer to the outside, making it more effective in improving efficiency.

아래의 화합물들은 본 발명에 따른 화합물의 구체적인 예들이다. 하기의 예들은 본 발명을 설명하기 위한 예시일 뿐이므로, 본 발명이 이에 한정되는 것은 아니다. The compounds below are specific examples of compounds according to the present invention. The following examples are only for illustrating the present invention, and the present invention is not limited thereto.

상기 본 발명의 화합물의 일 실시예는 하기의 개략적인 반응식으로 합성될 수 있다.One example of the compound of the present invention can be synthesized according to the schematic reaction scheme below.

<반응식1><Scheme 1>

한편, 본 발명은 또 다른 일실시예로서 상기 화학식 1로 표시되는 화합물을 포함하는 유기 발광 소자를 제공한다. 상기 유기 발광 소자는 제1전극, 제2 전극, 및 상기 제1 전극과 제2 전극의 내측에 개재되는 1층 이상의 유기물층을 포함하며, 상기 유기물층 중 하나 이상의 유기물층은 본 발명에 따른 화합물을 함유할 수 있다.Meanwhile, as another embodiment, the present invention provides an organic light-emitting device containing the compound represented by Formula 1 above. The organic light emitting device includes a first electrode, a second electrode, and one or more organic material layers interposed inside the first electrode and the second electrode, and one or more organic material layers of the organic material layers may contain a compound according to the present invention. You can.

본 발명의 일실시예에 있어서, 본 발명에 따른 화합물이 함유되는 유기물층은 정공주입층, 정공수송층 및 발광보조층 중 1층 이상일 수 있으며, 이때, 본 발명의 화합물은 단독으로 사용되거나 공지의 유기발광 화합물과 함께 사용될 수 있다. 구체적으로 상기 화합물은 정공주입층 및 정공수송층에 모두 포함될 수 있다. In one embodiment of the present invention, the organic material layer containing the compound according to the present invention may be one or more layers among a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer. In this case, the compound of the present invention is used alone or as a known organic layer. Can be used with luminescent compounds. Specifically, the compound may be included in both the hole injection layer and the hole transport layer.

본 발명에서 발광보조층이란 정공수송층과 발광층 사이에 형성되는 층으로, 정공수송층의 개수에 따라 제2정공수송층 또는 제3정공수송층 등으로도 지칭될 수 있다.In the present invention, the light-emitting auxiliary layer is a layer formed between the hole transport layer and the light-emitting layer, and may also be referred to as a second hole transport layer or a third hole transport layer, depending on the number of hole transport layers.

구체적으로 본 발명의 유기 발광 소자는 제1 전극과 제2 전극 사이에 정공주입층(HIL), 정공수송층(HTL), 발광층(EML), 전자수송층(ETL), 전자주입층(EIL) 등의 유기물층을 1 개 이상 포함할 수 있다. 한편, 본 발명의 일 구현예에 따르면, 유기 발광 소자는 제1 전극, 제2 전극, 제1 전극과 제2 전극의 내측에 개재되는 1층 이상의 유기물층, 및 캡핑층을 포함하여 구성될 수 있으며, 상기 캡핑층은 상기 제1 전극 및 제2 전극 중 어느 하나 이상의 전극의 외측에 배치될 수 있다.Specifically, the organic light emitting device of the present invention includes a hole injection layer (HIL), a hole transport layer (HTL), an emission layer (EML), an electron transport layer (ETL), and an electron injection layer (EIL) between the first electrode and the second electrode. It may include one or more organic layers. Meanwhile, according to one embodiment of the present invention, the organic light emitting device may include a first electrode, a second electrode, one or more organic material layers interposed inside the first electrode and the second electrode, and a capping layer. , the capping layer may be disposed on the outside of any one or more of the first electrode and the second electrode.

도 1은 본 발명의 일 실시예에 따른 유기 발광 소자의 구성을 보여주는 개략도이다.1 is a schematic diagram showing the configuration of an organic light-emitting device according to an embodiment of the present invention.

도 1에 도시된 바와 같이, 본 발명의 유기 발광 소자는 아래로부터 기판(100), 제1 전극(정공주입전극, 1000), 정공주입층(200), 정공수송층(300), 발광층(400), 전자수송층(500), 전자주입층(600), 제2 전극(전자주입전극,2000), 캡핑층(3000) 순으로 적층되어 제조될 수 있다. As shown in Figure 1, the organic light emitting device of the present invention includes, from below, a substrate 100, a first electrode (hole injection electrode, 1000), a hole injection layer 200, a hole transport layer 300, and a light emitting layer 400. , it can be manufactured by stacking the electron transport layer 500, the electron injection layer 600, the second electrode (electron injection electrode, 2000), and the capping layer 3000 in that order.

또한, 도시되지 않았으나, 발광층(400)과 전자수송층(500) 사이에 정공저지층(도시 생략됨)이 더 포함될 수 있으며, 정공수송층(300)과 발광층(400) 사이에 전자저지층(도시 생략됨)이 더 포함될 수 있다. In addition, although not shown, a hole blocking layer (not shown) may be further included between the light emitting layer 400 and the electron transport layer 500, and an electron blocking layer (not shown) may be included between the hole transport layer 300 and the light emitting layer 400. ) may be further included.

또한, 기판(100)과 제1 전극(1000) 사이에 캡핑층(도시 생략됨)이 더 포함될 수 있으며, 제2 전극(2000) 상부에 캡핑층(도시 생략됨)이 더 포함될 수 있다.Additionally, a capping layer (not shown) may be further included between the substrate 100 and the first electrode 1000, and a capping layer (not shown) may be further included on top of the second electrode 2000.

도 1에서 기판(100)은 유기 발광 소자에서 사용되는 기판을 사용할 수 있으며, 특히 기계적 강도, 열적 안정성, 투명성, 표면평활성, 취급용이성, 및 방수성이 우수한 투명한 유리 기판 또는 플렉시블이 가능한 플라스틱 기판일 수 있다.In FIG. 1, the substrate 100 may be a substrate used in an organic light emitting device. In particular, it may be a transparent glass substrate or a flexible plastic substrate with excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofing. there is.

제1 전극(1000)은 유기 발광 소자의 정공 주입을 위한 애노드로 사용된다. 정공의 주입이 가능하도록 낮은 일함수를 갖는 물질을 이용하며, 인듐틴옥사이드(ITO), 인듐징크옥사이드(IZO), 그래핀(graphene)과 같은 투명한 재질로 형성될 수 있다.The first electrode 1000 is used as an anode for hole injection into an organic light emitting device. A material with a low work function is used to enable hole injection, and it can be made of transparent materials such as indium tin oxide (ITO), indium zinc oxide (IZO), and graphene.

상기 제1 전극 상부에 정공주입층 물질을 진공증착법, 스핀코팅법, 캐스트법, LB(Langmuir-Blodgett)법 등과 같은 방법에 의해 증착하여 정공주입층(200)을 형성할 수 있다. 상기 진공증착법에 의해 정공주입층을 형성하는 경우 그 증착조건은 정공주입층의 재료로서 사용하는 화합물, 목적하는 정공주입층의 구조 및 열적특성 등에 따라 다르지만, 일반적으로 50-500℃의 증착온도, 10-8 내지 10-3 torr 의 진공도, 0.01 내지 100 Å/sec의 증착속도, 10 Å 내지 5 ㎛의 층 두께 범위에서 적절히 선택할 수 있다.The hole injection layer 200 may be formed by depositing a hole injection layer material on the top of the first electrode using a method such as vacuum deposition, spin coating, casting, or Langmuir-Blodgett (LB) method. When forming a hole injection layer by the vacuum deposition method, the deposition conditions vary depending on the compound used as the material for the hole injection layer, the structure and thermal characteristics of the desired hole injection layer, but generally a deposition temperature of 50-500°C, A vacuum degree of 10 -8 to 10 -3 torr, a deposition rate of 0.01 to 100 Å/sec, and a layer thickness of 10 Å to 5 ㎛ can be appropriately selected.

다음으로 상기 정공주입층(200) 상부에 정공수송층 물질을 진공증착법, 스핀코팅법, 캐스트법, LB법 등과 같은 방법에 의해 증착하여 정공수송층(300)을 형성할 수 있다. 상기 진공 증착법에 의해 정공 수송층을 형성하는 경우 그 증착조건은 사용하는 화합물에 따라 다르지만 일반적으로 정공주입층의 형성과 거의 동일한 조건 범위에서 선택하는 것이 좋다. 상기 정공수송층은 하나 이상일 수 있으며, 예를 들어, 제1정공수송층 및 제2정공수송층(발광보조층)의 두 개의 층일 수 있다. 상기 제1 정공수송층 및 제2 정공수송층 중 적어도 어느 하나는 본 발명에 따른 화학식 1의 화합물을 포함할 수 있다.Next, the hole transport layer 300 can be formed by depositing a hole transport layer material on top of the hole injection layer 200 by a method such as vacuum deposition, spin coating, casting, or LB method. When forming a hole transport layer by the vacuum deposition method, the deposition conditions vary depending on the compound used, but it is generally recommended to select conditions within the same range as those for forming the hole injection layer. The hole transport layer may be one or more, for example, it may be two layers: a first hole transport layer and a second hole transport layer (light-emitting auxiliary layer). At least one of the first hole transport layer and the second hole transport layer may include the compound of Formula 1 according to the present invention.

그 후, 상기 정공수송층 또는 발광보조층 상부에 발광층 물질을 진공증착법, 스핀코팅법, 캐스트법, LB법 등과 같은 방법에 의해 증착하여 발광층(400)을 형성할 수 있다. 상기 진공 증착법에 의해 발광층을 형성하는 경우 그 증착조건은 사용하는 화합물에 따라 다르지만 일반적으로 정공주입층의 형성과 거의 동일한 조건 범위에서 선택하는 것이 좋다. 또한, 상기 발광층 재료는 공지의 화합물을 호스트 또는 도펀트로 사용할 수 있다.Thereafter, the light-emitting layer 400 can be formed by depositing a light-emitting layer material on the hole transport layer or the light-emitting auxiliary layer by a method such as vacuum deposition, spin coating, casting, or LB method. When forming a light-emitting layer by the vacuum deposition method, the deposition conditions vary depending on the compound used, but it is generally recommended to select conditions within the same range as those for forming the hole injection layer. Additionally, the light emitting layer material may use a known compound as a host or dopant.

또한, 발광층에 인광 도펀트와 함께 사용할 경우에는 삼중항 여기자 또는 정공이 전자수송층으로 확산되는 현상을 방지하기 위하여 정공억제재료(HBL)를 추가로 진공증착법 또는 스핀코팅법에 의해 적층시킬 수 있다. 이때 사용할 수 있는 정공억제물질은 특별히 제한되지는 않으나, 정공억제재료로 사용되고 있는 공지의 것에서 임의의 것을 선택해서 이용할 수 있다. 예를 들면, 옥사디아졸 유도체나 트리아졸 유도체, 페난트롤린 유도체, 또는 일본특개평 11-329734(A1)에 기재되어 있는 정공억제재료 등을 들 수 있으며, 대표적으로 Balq(비스(8-하이드록시-2-메틸퀴놀리놀나토)-알루미늄 비페녹사이드), 페난트롤린(phenanthrolines)계 화합물(예: UDC사 BCP(바쏘쿠프로인)) 등을 사용할 수 있다.In addition, when used with a phosphorescent dopant in the light emitting layer, a hole blocking material (HBL) can be additionally laminated by vacuum deposition or spin coating to prevent diffusion of triplet excitons or holes into the electron transport layer. The hole blocking material that can be used at this time is not particularly limited, but any material can be selected from known hole blocking materials and used. For example, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, or hole blocking materials described in Japanese Patent Application Laid-Open No. 11-329734 (A1), etc., representative examples include Balq (bis (8-hyde) Roxy-2-methylquinolinolnato)-aluminum biphenoxide), phenanthrolines-based compounds (e.g., UDC's BCP (bassocuproin)), etc. can be used.

상기와 같이 형성된 발광층(400) 상부에는 전자수송층(500)이 형성되는데, 이때 상기 전자수송층은 진공증착법, 스핀코팅법, 캐스트법 등의 방법으로 형성할 수 있다. 또한, 상기 전자수송층의 증착조건은 사용하는 화합물에 따라 다르지만, 일반적으로 정공주입층의 형성과 거의 동일한 조건 범위에서 선택하는 것이 좋다.An electron transport layer 500 is formed on the light emitting layer 400 formed as described above. In this case, the electron transport layer can be formed by a method such as vacuum deposition, spin coating, or casting. In addition, the deposition conditions for the electron transport layer vary depending on the compound used, but it is generally better to select conditions within the same range as those for forming the hole injection layer.

그 뒤, 상기 전자수송층(500) 상부에 전자주입층 물질을 증착하여 전자주입층(600)을 형성할 수 있으며, 이때 상기 전자주입층은 통상의 전자주입층 물질을 진공증착법, 스핀코팅법, 캐스트법 등의 방법으로 형성할 수 있다.Thereafter, an electron injection layer material may be deposited on top of the electron transport layer 500 to form an electron injection layer 600. At this time, the electron injection layer may be formed using a typical electron injection layer material using a vacuum deposition method, a spin coating method, or a vacuum deposition method. It can be formed by a method such as a casting method.

전자주입층(600) 위에 전자 주입을 위한 제2 전극(2000)를 진공증착법이나 스퍼터링법 등의 방법에 의해 형성한다. 제2 전극으로는 다양한 금속이 사용될 수 있다. 구체적인 예로 알루미늄, 금, 은 등의 물질이 있다.A second electrode 2000 for electron injection is formed on the electron injection layer 600 by a method such as vacuum deposition or sputtering. Various metals may be used as the second electrode. Specific examples include materials such as aluminum, gold, and silver.

본 발명의 유기 발광 소자는 제1 전극(애노드), 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층, 제2 전극(캐소드) 구조의 유기 발광 소자뿐만 아니라, 다양한 구조의 유기 발광 소자의 구조가 가능하며, 필요에 따라 1층 또는 2층의 중간층을 더 형성하는 것도 가능하다.The organic light emitting device of the present invention includes not only an organic light emitting device having a structure of a first electrode (anode), a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a second electrode (cathode), but also an organic light emitting device having various structures. A structure of is possible, and it is also possible to form an additional one- or two-layer middle layer as needed.

상기와 같이 본 발명에 따라 형성되는 각 유기물층의 두께는 요구되는 정도에 따라 조절할 수 있으며, 구체적으로는 10 내지 1,000 ㎚이며, 더욱 구체적으로는 30 내지 100 ㎚인 것이 좋다.As described above, the thickness of each organic layer formed according to the present invention can be adjusted according to the required degree, and is preferably 10 to 1,000 nm, and more specifically 30 to 100 nm.

또한 본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 유기물층의 두께를 분자 단위로 조절할 수 있기 때문에 표면이 균일하며, 형태안정성이 뛰어난 장점이 있다.In addition, the present invention has the advantage that the organic material layer containing the compound represented by Formula 1 has a uniform surface and excellent morphological stability because the thickness of the organic material layer can be adjusted on a molecular basis.

이하에서는 본 발명의 일실시예에 따른 화합물의 합성예 및 유기 발광 소자 제조예를 통하여 본 발명을 더 상세하게 설명한다. 하기 실시예는 본 발명을 예시하는 것일 뿐 본 발명의 범위가 하기 실시예에 한정되는 것은 아니다.Hereinafter, the present invention will be described in more detail through examples of compound synthesis and organic light-emitting device manufacturing examples according to an embodiment of the present invention. The following examples are merely illustrative of the present invention and the scope of the present invention is not limited to the following examples.

합성예 1: 화합물 22의 합성Synthesis Example 1: Synthesis of Compound 22

둥근바닥플라스크에 ((4-bromophenyl)methanetriyl)tribenzene 2.8g, N-([1,1':4',1''-terphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine 3.0g, t-BuONa 1.0g, Pd2(dba)3 0.2g, (t-Bu)3P 0.3ml를 톨루엔 120ml에 녹인 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결하였다. 유기층을 MC로 추출하고 감압여과한 후 컬럼정제 및 재결정하여 화합물 22 3.6g (수율 69%)을 얻었다.In a round bottom flask, 2.8g of ((4-bromophenyl)methanetriyl)tribenzene, N-([1,1':4',1''-terphenyl]-2-yl)-5,5,8,8-tetramethyl- 3.0 g of 5,6,7,8-tetrahydronaphthalen-2-amine, 1.0 g of t-BuONa, 0.2 g of Pd 2 (dba) 3 , and 0.3 ml of (t-Bu) 3 P were dissolved in 120 ml of toluene and stirred under reflux. The reaction was confirmed by TLC and the reaction was terminated after adding water. The organic layer was extracted with MC, filtered under reduced pressure, then column purified and recrystallized to obtain 3.6 g of Compound 22 (yield 69%).

m/z: 749.40 (100.0%), 750.41 (62.2%), 751.41 (19.0%), 752.41 (3.8%)m/z: 749.40 (100.0%), 750.41 (62.2%), 751.41 (19.0%), 752.41 (3.8%)

합성예 2: 화합물 346의 합성Synthesis Example 2: Synthesis of Compound 346

합성예 1과 같은 방법으로 ((4-bromophenyl)methanetriyl)tribenzene 대신 (3-bromophenyl)triphenylsilane을 이용하여 화합물 346을 합성하였다(수율64%).Compound 346 was synthesized in the same manner as Synthesis Example 1, using (3-bromophenyl)triphenylsilane instead of ((4-bromophenyl)methanetriyl)tribenzene (yield 64%).

m/z: 765.38 (100.0%), 766.38 (66.0%), 767.39 (18.4%), 767.38 (6.7%), 768.39 (4.5%), 768.38 (2.1%)m/z: 765.38 (100.0%), 766.38 (66.0%), 767.39 (18.4%), 767.38 (6.7%), 768.39 (4.5%), 768.38 (2.1%)

합성예 3: 화합물 530의 합성Synthesis Example 3: Synthesis of Compound 530

합성예 1과 같은 방법으로 ((4-bromophenyl)methanetriyl)tribenzene 대신 (3'-bromo-[1,1'-biphenyl]-3-yl)triphenylsilane을 이용하여 화합물 530을 합성하였다(수율62%).Compound 530 was synthesized in the same manner as in Synthesis Example 1, using (3'-bromo-[1,1'-biphenyl]-3-yl)triphenylsilane instead of ((4-bromophenyl)methanetriyl)tribenzene (yield 62%). .

m/z: 841.41 (100.0%), 842.41 (72.5%), 843.42 (22.6%), 843.41 (7.0%), 844.42 (6.1%), 844.41 (2.4%), 845.42 (1.0%)m/z: 841.41 (100.0%), 842.41 (72.5%), 843.42 (22.6%), 843.41 (7.0%), 844.42 (6.1%), 844.41 (2.4%), 845.42 (1.0%)

합성예 4: 화합물 549의 합성Synthesis Example 4: Synthesis of Compound 549

합성예 1과 같은 방법으로 ((4-bromophenyl)methanetriyl)tribenzene 및 N-([1,1':4',1''-terphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine 대신 (2'-bromo-[1,1'-biphenyl]-4-yl)triphenylsilane 및 N-([1,1'-biphenyl]-4-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine을 이용하여 화합물 549를 합성하였다(수율73%).In the same manner as Synthesis Example 1, ((4-bromophenyl)methanetriyl)tribenzene and N-([1,1':4',1''-terphenyl]-2-yl)-5,5,8,8-tetramethyl - Instead of 5,6,7,8-tetrahydronaphthalen-2-amine, use (2'-bromo-[1,1'-biphenyl]-4-yl)triphenylsilane and N-([1,1'-biphenyl]-4- Compound 549 was synthesized using yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine (yield 73%).

m/z: 765.38 (100.0%), 766.38 (66.0%), 767.39 (18.4%), 767.38 (6.7%), 768.39 (4.5%), 768.38 (2.1%)m/z: 765.38 (100.0%), 766.38 (66.0%), 767.39 (18.4%), 767.38 (6.7%), 768.39 (4.5%), 768.38 (2.1%)

합성예 5: 화합물 550의 합성Synthesis Example 5: Synthesis of Compound 550

합성예 1과 같은 방법으로 ((4-bromophenyl)methanetriyl)tribenzene 및 N-([1,1':4',1''-terphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine 대신 (2'-bromo-[1,1'-biphenyl]-4-yl)triphenylsilane 및 N-([1,1'-biphenyl]-3-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine을 이용하여 화합물 550을 합성하였다(수율65%).In the same manner as Synthesis Example 1, ((4-bromophenyl)methanetriyl)tribenzene and N-([1,1':4',1''-terphenyl]-2-yl)-5,5,8,8-tetramethyl - Instead of 5,6,7,8-tetrahydronaphthalen-2-amine, use (2'-bromo-[1,1'-biphenyl]-4-yl)triphenylsilane and N-([1,1'-biphenyl]-3- Compound 550 was synthesized using yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine (yield 65%).

m/z: 765.38 (100.0%), 766.38 (66.0%), 767.39 (18.4%), 767.38 (6.7%), 768.39 (4.5%), 768.38 (2.1%)m/z: 765.38 (100.0%), 766.38 (66.0%), 767.39 (18.4%), 767.38 (6.7%), 768.39 (4.5%), 768.38 (2.1%)

합성예 6: 화합물 551의 합성Synthesis Example 6: Synthesis of Compound 551

합성예 1과 같은 방법으로 ((4-bromophenyl)methanetriyl)tribenzene 및 N-([1,1':4',1''-terphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine 대신 (2'-bromo-[1,1'-biphenyl]-4-yl)triphenylsilane 및 N-([1,1'-biphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine을 이용하여 화합물 551을 합성하였다(수율70%).In the same manner as Synthesis Example 1, ((4-bromophenyl)methanetriyl)tribenzene and N-([1,1':4',1''-terphenyl]-2-yl)-5,5,8,8-tetramethyl - Instead of 5,6,7,8-tetrahydronaphthalen-2-amine, use (2'-bromo-[1,1'-biphenyl]-4-yl)triphenylsilane and N-([1,1'-biphenyl]-2- Compound 551 was synthesized using yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine (yield 70%).

m/z: 765.38 (100.0%), 766.38 (66.0%), 767.39 (18.4%), 767.38 (6.7%), 768.39 (4.5%), 768.38 (2.1%)m/z: 765.38 (100.0%), 766.38 (66.0%), 767.39 (18.4%), 767.38 (6.7%), 768.39 (4.5%), 768.38 (2.1%)

합성예 7: 화합물 565의 합성Synthesis Example 7: Synthesis of Compound 565

합성예 1과 같은 방법으로 ((4-bromophenyl)methanetriyl)tribenzene 대신 (2'-bromo-[1,1'-biphenyl]-4-yl)triphenylsilane을 이용하여 화합물 565를 합성하였다(수율71%).Compound 565 was synthesized in the same manner as Synthesis Example 1, using (2'-bromo-[1,1'-biphenyl]-4-yl)triphenylsilane instead of ((4-bromophenyl)methanetriyl)tribenzene (yield 71%). .

m/z: 841.41 (100.0%), 842.41 (72.5%), 843.42 (22.6%), 843.41 (7.0%), 844.42 (6.1%), 844.41 (2.4%), 845.42 (1.0%)m/z: 841.41 (100.0%), 842.41 (72.5%), 843.42 (22.6%), 843.41 (7.0%), 844.42 (6.1%), 844.41 (2.4%), 845.42 (1.0%)

합성예 8: 화합물 574의 합성Synthesis Example 8: Synthesis of Compound 574

합성예 1과 같은 방법으로 ((4-bromophenyl)methanetriyl)tribenzene 및 N-([1,1':4',1''-terphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine 대신 (2'-bromo-[1,1'-biphenyl]-4-yl)triphenylsilane 및 9,9-dimethyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-9H-fluoren-2-amine을 이용하여 화합물 574를 합성하였다(수율70%).In the same manner as Synthesis Example 1, ((4-bromophenyl)methanetriyl)tribenzene and N-([1,1':4',1''-terphenyl]-2-yl)-5,5,8,8-tetramethyl - Instead of 5,6,7,8-tetrahydronaphthalen-2-amine, use (2'-bromo-[1,1'-biphenyl]-4-yl)triphenylsilane and 9,9-dimethyl-N-(5,5,8 Compound 574 was synthesized using ,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-9H-fluoren-2-amine (yield 70%).

m/z: 805.41 (100.0%), 806.41 (69.3%), 807.42 (20.5%), 807.41 (6.8%), 808.42 (5.3%), 808.41 (2.2%)m/z: 805.41 (100.0%), 806.41 (69.3%), 807.42 (20.5%), 807.41 (6.8%), 808.42 (5.3%), 808.41 (2.2%)

합성예 9: 화합물 552의 합성Synthesis Example 9: Synthesis of Compound 552

합성예 1과 같은 방법으로 ((4-bromophenyl)methanetriyl)tribenzene 및 N-([1,1':4',1''-terphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine 대신 (2'-bromo-[1,1'-biphenyl]-4-yl)triphenylsilane 및 bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine을 이용하여 화합물 552를 합성하였다(수율67%).In the same manner as Synthesis Example 1, ((4-bromophenyl)methanetriyl)tribenzene and N-([1,1':4',1''-terphenyl]-2-yl)-5,5,8,8-tetramethyl -5,6,7,8-tetrahydronaphthalen-2-amine instead of (2'-bromo-[1,1'-biphenyl]-4-yl)triphenylsilane and bis(5,5,8,8-tetramethyl-5, Compound 552 was synthesized using 6,7,8-tetrahydronaphthalen-2-yl)amine (yield 67%).

m/z: 799.46 (100.0%), 800.46 (68.5%), 801.46 (22.8%), 802.47 (4.1%), 801.45 (3.4%), 802.46 (3.2%)m/z: 799.46 (100.0%), 800.46 (68.5%), 801.46 (22.8%), 802.47 (4.1%), 801.45 (3.4%), 802.46 (3.2%)

합성예 10: 화합물 717의 합성Synthesis Example 10: Synthesis of Compound 717

합성예 1과 같은 방법으로 ((4-bromophenyl)methanetriyl)tribenzene 및 N-([1,1':4',1''-terphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine 대신 (2''-bromo-[1,1':4',1''-terphenyl]-4-yl)triphenylsilane 및 bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine을 이용하여 화합물 717을 합성하였다(수율60%).In the same manner as Synthesis Example 1, ((4-bromophenyl)methanetriyl)tribenzene and N-([1,1':4',1''-terphenyl]-2-yl)-5,5,8,8-tetramethyl -5,6,7,8-tetrahydronaphthalen-2-amine instead of (2''-bromo-[1,1':4',1''-terphenyl]-4-yl)triphenylsilane and bis(5,5, Compound 717 was synthesized using 8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine (yield 60%).

m/z: 875.49 (100.0%), 876.49 (75.4%), 877.50 (24.1%), 877.49 (7.2%), 878.50 (5.5%), 878.49 (3.6%), 879.50 (1.2%)m/z: 875.49 (100.0%), 876.49 (75.4%), 877.50 (24.1%), 877.49 (7.2%), 878.50 (5.5%), 878.49 (3.6%), 879.50 (1.2%)

합성예 11 내지 합성예 25Synthesis Examples 11 to 25

합성예 1과 같은 방법으로 ((4-bromophenyl)methanetriyl)tribenzene 및 N-([1,1':4',1''-terphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine 대신 하기 표 1의 출발물질 1 및 출발물질 2를 사용하여 화합물을 합성하였다.In the same manner as Synthesis Example 1, ((4-bromophenyl)methanetriyl)tribenzene and N-([1,1':4',1''-terphenyl]-2-yl)-5,5,8,8-tetramethyl Compounds were synthesized using starting materials 1 and 2 in Table 1 below instead of -5,6,7,8-tetrahydronaphthalen-2-amine.

출발물질1Starting material 1 출발물질2Starting material 2 m/zm/z 합성예11Synthesis Example 11 화합물555Compound 555 m/z: 815.39 (100.0%)m/z: 815.39 (100.0%) 합성예12Synthesis Example 12 화합물570Compound 570 m/z: 865.41 (100.0%)m/z: 865.41 (100.0%) 합성예13Synthesis Example 13 화합물592Compound 592 m/z: 855.39 (100.0%)m/z: 855.39 (100.0%) 합성예14Synthesis Example 14 화합물602Compound 602 m/z: 871.37 (100.0%)m/z: 871.37 (100.0%) 합성예15Synthesis Example 15 화합물621Compound 621 m/z: 875.49 (100.0%)m/z: 875.49 (100.0%) 합성예16Synthesis Example 16 화합물747Compound 747 m/z: 751.36 (100.0%)m/z: 751.36 (100.0%) 합성예17Synthesis Example 17 화합물799Compound 799 m/z: 721.32 (100.0%)m/z: 721.32 (100.0%) 합성예18Synthesis Example 18 화합물805Compound 805 m/z: 735.33 (100.0%)m/z: 735.33 (100.0%) 합성예19Synthesis Example 19 화합물811Compound 811 m/z: 779.39 (100.0%)m/z: 779.39 (100.0%) 합성예20Synthesis Example 20 화합물829Compound 829 m/z: 697.28 (100.0%)m/z: 697.28 (100.0%) 합성예21Synthesis Example 21 화합물838Compound 838 m/z: 727.29 (100.0%)m/z: 727.29 (100.0%) 합성예22Synthesis example 22 화합물850Compound 850 m/z: 711.30 (100.0%)m/z: 711.30 (100.0%) 합성예23Synthesis example 23 화합물859Compound 859 m/z: 713.28 (100.0%)m/z: 713.28 (100.0%) 합성예24Synthesis example 24 화합물883Compound 883 m/z: 811.35 (100.0%)m/z: 811.35 (100.0%) 합성예25Synthesis example 25 화합물894Compound 894 m/z: 715.27 (100.0%)m/z: 715.27 (100.0%)

유기 발광 소자의 제조Manufacturing of organic light emitting devices

도 1은 일반적인 유기 발광 소자의 구조를 나타낸 것으로서, 본 발명은 예시로서, 도 1에 나타낸 유기 발광 소자의 구조를 갖도록 제조하였다. 구체적으로, 제조된 유기 발광 소자는 아래로부터 양극(정공주입전극(1000)) / 정공주입층(200) / 정공수송층(300) / 발광층(400) / 전자수송층(500) / 전자주입층(600) / 음극(전자주입전극(2000)) / 캡핑층(3000) 순으로 적층되어 있다.Figure 1 shows the structure of a general organic light-emitting device, and the present invention is an example, and the organic light-emitting device was manufactured to have the structure shown in Figure 1. Specifically, the manufactured organic light emitting device is, from below, an anode (hole injection electrode (1000)) / hole injection layer (200) / hole transport layer (300) / light emitting layer (400) / electron transport layer (500) / electron injection layer (600) ) / cathode (electron injection electrode (2000)) / capping layer (3000) are laminated in that order.

유기 발광 소자 제작 시, 기판(10)은 투명한 유리 기판 또는 플렉시블이 가능한 플라스틱 기판일 수 있다.When manufacturing an organic light emitting device, the substrate 10 may be a transparent glass substrate or a flexible plastic substrate.

정공주입전극(1000)은 유기 발광 소자의 정공 주입을 위한 양극으로 사용된다. 정공의 주입이 가능하도록 낮은 일함수를 갖는 물질을 이용하며, 인듐틴옥사이드(ITO), 인듐징크옥사이드(IZO), 그래핀(grapheme)과 같은 투명한 재질로 형성될 수 있다.The hole injection electrode 1000 is used as an anode for hole injection into an organic light emitting device. A material with a low work function is used to enable hole injection, and it can be made of transparent materials such as indium tin oxide (ITO), indium zinc oxide (IZO), and graphene.

정공주입층(200), 정공수송층(300), 발광층(400), 전자수송층(500), 전자주입층(600), 고굴절 캡핑층에는 하기 표 2에 정리된 물질들을 사용하였다.The materials listed in Table 2 below were used for the hole injection layer 200, the hole transport layer 300, the light emitting layer 400, the electron transport layer 500, the electron injection layer 600, and the high refractive index capping layer.

또한, 전자주입층(600) 위에 전자 주입을 위한 음극(2000)을 형성하였다. 음극으로는 다양한 금속이 사용될 수 있다. 구체적인 예로 알루미늄, 금, 은, 마그네슘, 마그네슘-은 합금 등의 물질이 있다.Additionally, a cathode 2000 for electron injection was formed on the electron injection layer 600. Various metals can be used as the cathode. Specific examples include materials such as aluminum, gold, silver, magnesium, and magnesium-silver alloy.

NDP9NDP9 BH01BH01 BD01BD01 ET01ET01 LiqLiq CPM01CPM01

실시예 1Example 1

은(Ag)을 포함하는 반사층이 형성된 인듐틴옥사이드(ITO) 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시켰다. 이후 ITO 기판 상부에 정공주입층으로 합성예 1에서 제조된 화합물에 NDP9를 3중량%로 도핑하여 100 Å, 정공수송층으로 합성예 1에서 제조된 화합물 1500 Å 두께로 증착시켰다. 발광층으로 호스트 BH01에 도판트 BD01을 3중량%로 도핑하여 250 Å 두께로 증착하였다. 그런 다음 전자수송층으로 ET01 및 Liq(1:1, wt./wt.)의 혼합물을 300 Å 두께로 증착한 후 LiF 10Å 두께로 증착하여 전자주입층을 형성하였다. 이어서 MgAg을 15nm의 두께로 증착하여 음극을 형성하였고, 상기 음극 위에 캡핑층으로 CPM01을 950 Å두께로 증착시켰다. 이 소자를 글로브 박스에서 밀봉(Encapsulation)함으로써 유기 발광 소자를 제작하였다.The indium tin oxide (ITO) substrate on which the reflective layer containing silver (Ag) was formed was washed with distilled water ultrasonic waves. After washing with distilled water, it was ultrasonic washed with solvents such as isopropyl alcohol, acetone, and methanol and dried. Afterwards, the compound prepared in Synthesis Example 1 as a hole injection layer was doped with 3% by weight of NDP9 on the top of the ITO substrate to have a thickness of 100 Å, and the compound prepared in Synthesis Example 1 as a hole transport layer was deposited to a thickness of 1500 Å. As an emitting layer, host BH01 was doped with 3% by weight of dopant BD01 and deposited to a thickness of 250 Å. Then, a mixture of ET01 and Liq (1:1, wt./wt.) was deposited to a thickness of 300 Å as an electron transport layer, and then LiF was deposited to a thickness of 10 Å to form an electron injection layer. Next, MgAg was deposited to a thickness of 15 nm to form a cathode, and CPM01 was deposited to a thickness of 950 Å as a capping layer on the cathode. An organic light-emitting device was manufactured by encapsulating this device in a glove box.

실시예 2 내지 실시예 25Examples 2 to 25

상기 실시예 1과 같은 방법으로 제조하되, 각각 합성예 2 내지 합성예 25에서 제조된 화합물을 사용하여, 정공주입 및 정공수송층으로 제막한 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, but using the compounds prepared in Synthesis Examples 2 to 25, respectively, to form a hole injection and hole transport layer.

비교예 1 내지 비교예 7Comparative Examples 1 to 7

상기 실시예 1과 같은 방법으로 제조하되, 하기 표 3에 표시된 비교화합물 1 내지 비교화합물 7을 각각 사용하여, 정공주입 및 정공수송층으로 제막한 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, but using Comparative Compounds 1 to 7 shown in Table 3 below, respectively, to form a hole injection and hole transport layer.

비교화합물1Comparative compound 1 비교화합물2Comparative compound 2 비교화합물3Comparative compound 3 비교화합물4Comparative compound 4 비교화합물5Comparative compound 5 비교화합물6Comparative compound 6 비교화합물7Comparative compound 7

<실험예 1> 유기 발광 소자의 성능평가<Experimental Example 1> Performance evaluation of organic light emitting device

키슬리 2400 소스 메져먼트 유닛(Kiethley 2400 source measurement unit) 으로 전압을 인가하여 전자 및 정공을 주입하고 코니카 미놀타(Konica Minolta) 분광복사계(CS-2000)를 이용하여 빛이 방출될 때의 휘도를 측정함으로써, 실시예 1 내지 실시예 10 및 비교예 1 내지 비교예 7의 유기발광소자의 성능을 인가전압에 대한 전류 밀도 및 휘도를 대기압 조건하에 측정하여 평가하였으며, 그 결과를 표 4에 나타내었다.Apply voltage to the Keithley 2400 source measurement unit to inject electrons and holes, and measure the luminance when light is emitted using a Konica Minolta spectroradiometer (CS-2000). By doing so, the performance of the organic light-emitting devices of Examples 1 to 10 and Comparative Examples 1 to 7 was evaluated by measuring the current density and luminance with respect to the applied voltage under atmospheric pressure conditions, and the results are shown in Table 4.

Op. VOp. V mA/cm2mA/cm2 Cd/ACd/A QE(%)QE(%) CIExCIEx CIEyCIey LT95LT95 실시예1Example 1 3.663.66 1010 8.58.5 7.47.4 0.1390.139 0.0500.050 153153 실시예2Example 2 3.613.61 1010 9.19.1 8.18.1 0.1400.140 0.0490.049 160160 실시예3Example 3 3.633.63 1010 9.19.1 8.08.0 0.1400.140 0.0490.049 165165 실시예4Example 4 3.593.59 1010 9.39.3 8.38.3 0.1420.142 0.0490.049 160160 실시예5Example 5 3.623.62 1010 9.69.6 8.58.5 0.1400.140 0.0490.049 160160 실시예6Example 6 3.603.60 1010 9.79.7 8.68.6 0.1400.140 0.0480.048 167167 실시예7Example 7 3.603.60 1010 9.89.8 8.88.8 0.1400.140 0.0480.048 175175 실시예8Example 8 3.583.58 1010 8.98.9 8.08.0 0.1400.140 0.0490.049 162162 실시예9Example 9 3.543.54 1010 9.29.2 8.68.6 0.1390.139 0.0470.047 164164 실시예10Example 10 3.543.54 1010 9.29.2 8.68.6 0.1400.140 0.0480.048 170170 비교예1Comparative Example 1 3.823.82 1010 6.26.2 5.75.7 0.1400.140 0.1110.111 113113 비교예2Comparative example 2 4.104.10 1010 6.56.5 6.06.0 0.1410.141 0.1120.112 100100 비교예3Comparative example 3 4.004.00 1010 6.06.0 6.36.3 0.1400.140 0.1100.110 9292 비교예4Comparative example 4 3.833.83 1010 7.27.2 5.95.9 0.1420.142 0.0500.050 55 비교예5Comparative Example 5 3.923.92 1010 7.47.4 6.66.6 0.1400.140 0.0500.050 22 비교예6Comparative Example 6 3.873.87 1010 6.76.7 5.25.2 0.0140.014 0.0510.051 6262 비교예7Comparative example 7 4.224.22 1010 7.87.8 6.96.9 0.0140.014 0.0500.050 8080

표 4에서 볼 수 있듯이, 본 발명의 실시예들을 비교해보면, 비교예 1 내지 비교예 5와 비교하여, 축합된 아릴사이클릭기를 가짐으로써 정공수송영역에 적절한 HOMO 형성 및 빠른 홀 모빌리티를 가지고 높은 LUMO 및 T1을 형성할 수 있어, 발광층내 전하밸런스가 좋고 롤오프현상이 억제되어 낮은 구동전압, 고효율 및 장수명 유기 발광소자를 구현할 수 있다. 동시에 축합된 아릴사이클릭기로 낮은 굴절률을 형성하여, 광추출 효과를 극대화해 더욱이 효율이 개선됨을 알 수 있다. 또한, 비교예4 내지 비교예6과 비교하여, 아릴알킬기 또는 아릴실릴기로 낮은 굴절률을 유지하며, 동시에 박막의 분자배열이 우수하여 빠른 모빌리티를 가지고 높은 열안정성을 가져, 구동전압, 효율 및 수명이 현저히 개선됨을 알 수 있다. 또한, 비교예7과 비교하여, 직접결합이나 파이컨주게이션을 가진 아릴렌 연결기로 높은 HOMO를 형성함과 동시에 빠른 홀 모빌리티로, 발광층내 전하균형이 원할하여, 낮은 구동전압, 고효율, 및 장수명 유기 발광 소자를 구현할 수 있다.As can be seen in Table 4, comparing the examples of the present invention, compared to Comparative Examples 1 to 5, by having a condensed arylcyclic group, HOMO formation suitable for the hole transport region and high LUMO with fast hole mobility are achieved. and T1 can be formed, so that the charge balance within the light emitting layer is good and the roll-off phenomenon is suppressed, making it possible to implement an organic light emitting device with low driving voltage, high efficiency, and long lifespan. At the same time, it can be seen that the condensed arylcyclic group forms a low refractive index, maximizing the light extraction effect and further improving efficiency. In addition, compared to Comparative Examples 4 to 6, a low refractive index is maintained by the arylalkyl group or arylsilyl group, and at the same time, the molecular arrangement of the thin film is excellent, so it has fast mobility and high thermal stability, and the driving voltage, efficiency, and lifespan are improved. It can be seen that there is significant improvement. In addition, compared to Comparative Example 7, high HOMO is formed by an arylene linker with direct bonding or pi-conjugation, and at the same time, charge balance in the light emitting layer is smooth due to fast hole mobility, resulting in low driving voltage, high efficiency, and long-life organic matter. A light emitting device can be implemented.

<실험예 2> 굴절률의 평가<Experimental Example 2> Evaluation of refractive index

화합물22, 화합물 346, 화합물 551, 화합물 552 및 비교화합물 1, 비교화합물 2, 비교화합물6을 각각 이용하여, 실리콘 기판 상에 두께 30nm의 증착막을 진공 증착 장비를 이용하여 제작하고, 엘립소미터 장치(J.A.Woollam Co. Inc, M-2000X)를 이용하여 450nm파장에서의 굴절률을 측정하였다. 그 결과는 하기 표 5에 정리된 바와 같다. 표 5에서 볼 수 있듯이, 본 발명의 화합물들은 450nm 파장에서 굴절률이 1.70 이하로 비교화합물에 비하여 낮은 굴절률을 갖는 것을 확인할 수 있다.Using Compound 22, Compound 346, Compound 551, Compound 552, and Comparative Compound 1, Comparative Compound 2, and Comparative Compound 6, respectively, a 30 nm thick deposition film was produced on a silicon substrate using vacuum deposition equipment, and an ellipsometer device was used. The refractive index at a wavelength of 450 nm was measured using (J.A. Woollam Co. Inc, M-2000X). The results are summarized in Table 5 below. As can be seen in Table 5, it can be seen that the compounds of the present invention have a lower refractive index than the comparative compounds, with a refractive index of 1.70 or less at a wavelength of 450 nm.

비교
화합물1comparison
Compound 1 비교
화합물2comparison
Compound 2 비교
화합물6comparison
Compound 6 화합물
22compound
22 화합물
346compound
346 화합물
551compound
551 화합물
552compound
552 n@450nm n@450nm 1.951.95 1.931.93 2.012.01 1.671.67 1.651.65 1.641.64 1.631.63

100: 기판
200: 정공주입층
300: 정공수송층
400: 발광층
500: 전자수송층
600: 전자주입층
1000: 제1 전극(애노드)
2000: 제2 전극(캐소드)
3000: 캡핑층100: substrate
200: Hole injection layer
300: Hole transport layer
400: light emitting layer
500: electron transport layer
600: Electron injection layer
1000: First electrode (anode)
2000: Second electrode (cathode)
3000: capping layer

Claims (18)

하기 화학식 1로 표현되는 화합물;
<화학식 1>


<화학식 1-1>


(상기 화학식 1에서,
X는 C, Si, Ge, Sn 또는 Pb이며,
ArCy는 상기 [화학식1-1]로 표시되는 축합환기이며,
Ar은 치환 또는 비치환된 C3~C50의 아릴기, 또는 치환 또는 비치환된 C2~C50의 헤테로아릴기이며,
Cy는 치환 또는 비치환된 C1~C50의 사이클로알킬기, 또는 C0~C50의 헤테로사이클릭기이고,
Ar1 및 Ar2는 각각 독립적으로 치환 또는 비치환된 C3~C50의 아릴기, 치환 또는 비치환된 C2~C50의 헤테로아릴기, 또는 상기 [화학식1-1]이고,
L1 내지 L3는 각각 독립적으로 직접결합, 치환 또는 비치환된 C3~C50의 아릴렌기, 치환 또는 비치환된 C2~C50의 헤테로아릴렌기이고,
R1 및 R2는 각각 독립적으로 수소, 중수소, 할로겐, 니트로기, 니트릴기, 하이드록시기, 티올기, 치환 또는 비치환된 아미노기, 치환 또는 비치환된 C1~C50의 알킬기, 치환 또는 비치환된 C2~C50의 알케닐기, 치환 또는 비치환된 C1~C50의 알콕시기, 치환 또는 비치환된 C1~C50의 설파이드기, 치환 또는 비치환된 C0~C50의 실릴기, 치환 또는 비치환된 C3~C50의 사이클로알킬기, 치환 또는 비치환된 C3~C50의 사이클로알케닐기, 치환 또는 비치환된 C1~C50의 헤테로사이클릴기, 치환 또는 비치환된 C3~C50의 아릴기, 또는 치환 또는 비치환된 C2~C50의 헤테로아릴기이다).
A compound represented by the following formula (1);
<Formula 1>


<Formula 1-1>


(In Formula 1 above,
X is C, Si, Ge, Sn or Pb,
ArCy is a condensed ring group represented by [Formula 1-1] above,
Ar is a substituted or unsubstituted C3~C50 aryl group, or a substituted or unsubstituted C2~C50 heteroaryl group,
Cy is a substituted or unsubstituted C1~C50 cycloalkyl group, or a C0~C50 heterocyclic group,
Ar1 and Ar2 are each independently a substituted or unsubstituted C3 to C50 aryl group, a substituted or unsubstituted C2 to C50 heteroaryl group, or the above [Formula 1-1],
L1 to L3 are each independently a direct bond, a substituted or unsubstituted C3 to C50 arylene group, or a substituted or unsubstituted C2 to C50 heteroarylene group,
R1 and R2 are each independently hydrogen, deuterium, halogen, nitro group, nitrile group, hydroxy group, thiol group, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C50 alkyl group, substituted or unsubstituted C2 ~C50 alkenyl group, substituted or unsubstituted C1~C50 alkoxy group, substituted or unsubstituted C1~C50 sulfide group, substituted or unsubstituted C0~C50 silyl group, substituted or unsubstituted C3~C50 cycloalkyl group, substituted or unsubstituted C3~C50 cycloalkenyl group, substituted or unsubstituted C1~C50 heterocyclyl group, substituted or unsubstituted C3~C50 aryl group, or substituted or unsubstituted C2~ It is the heteroaryl group of C50).
 제1항에 있어서,
상기 화학식 1은 하기 화학식 2로 표현되는 화합물;

<화학식 2>

(상기 화학식 2에서,
상기 화학식 1과 동일한 기호는 화학식 1에서의 정의와 동일하며,
R3는 상기 R1 및 R2의 정의와 동일하며, 인접한 R3끼리 연결되어 환을 형성할 수도 있으며,
l은 0 내지 3의 정수이다).
According to paragraph 1,
Formula 1 is a compound represented by Formula 2 below;

<Formula 2>

(In Formula 2 above,
Symbols identical to those in Formula 1 are the same as those defined in Formula 1,
R3 is the same as the definition of R1 and R2 above, and adjacent R3s may be connected to form a ring,
l is an integer from 0 to 3).
 제1항에 있어서,
상기 화학식 1은 하기 화학식 3으로 표현되는 화합물;

<화학식 3>

(상기 화학식 3에서,
상기 화학식 1과 동일한 기호는 화학식 1에서의 정의와 동일하며,
Z는 각각 독립적으로 CRR`, O, S, NR, SiRR` 또는 GeRR`이며,
R3, R 및 R'는 각각 독립적으로 상기 R1 및 R2의 정의와 동일하며, R3, R 및 R’ 중 2개 이상이 연결되어 환을 형성할 수도 있으며,
l은 0 내지 3의 정수이며,
m는 1 내지 5의 정수이다).
According to paragraph 1,
Formula 1 is a compound represented by Formula 3 below;

<Formula 3>

(In Formula 3 above,
Symbols identical to those in Formula 1 are the same as those defined in Formula 1,
Z is each independently CRR`, O, S, NR, SiRR` or GeRR`,
R3, R and R' are each independently the same as the definitions of R1 and R2 above, and two or more of R3, R and R' may be connected to form a ring,
l is an integer from 0 to 3,
m is an integer from 1 to 5).
 제1항에 있어서,
상기 화학식 1은 하기 화학식 4로 표현되는 화합물;

<화학식 4>

(상기 화학식 4에서,
상기 화학식 1과 동일한 기호는 화학식 1에서의 정의와 동일하며,
Z는 각각 독립적으로 CRR`, O, S, NR, SiRR` 또는 GeRR`이며,
R3, R4, R 및 R'는 각각 독립적으로 상기 R1 및 R2의 정의와 동일하며, R3, R 및 R’ 중 2개 이상이 연결되어 환을 형성할 수도 있으며, R4, R 및 R’ 중 2개 이상이 연결되어 환을 형성할 수도 있으며,
l은 각각 독립적으로 0 내지 3의 정수이며,
m 및 n은 각각 독립적으로 1 내지 5의 정수이다).
According to paragraph 1,
Formula 1 is a compound represented by Formula 4 below;

<Formula 4>

(In Formula 4 above,
Symbols identical to those in Formula 1 are the same as those defined in Formula 1,
Z is each independently CRR`, O, S, NR, SiRR` or GeRR`,
R3, R4, R and R' are each independently the same as the definitions of R1 and R2 above, and two or more of R3, R and R' may be connected to form a ring, and two of R4, R and R' may be connected. More than one may be connected to form a ring,
l is each independently an integer from 0 to 3,
m and n are each independently integers from 1 to 5).
 제1항에 있어서,
ArCy는 하기 화학식 1-2 또는 화학식1-3으로 표현되는 화합물;

<화학식 1-2>


<화학식 1-3>

(상기 화학식 1-2 및 화학식 1-3에서,
상기 Z는 각각 독립적으로 CRR`, O, S, NR 또는 SiRR`이며,
R 및 R'는 각각 독립적으로 상기 화학식 1의 R1 및 R2의 정의와 동일하며, R 및 R’ 중 2개 이상이 연결되어 환을 형성할 수도 있다).
According to paragraph 1,
ArCy is a compound represented by the following formula 1-2 or formula 1-3;

<Formula 1-2>


<Formula 1-3>

(In Formula 1-2 and Formula 1-3,
The Z is each independently CRR`, O, S, NR or SiRR`,
R and R' are each independently the same as the definitions of R1 and R2 in Formula 1 above, and two or more of R and R' may be connected to form a ring).
 제1항에 있어서,
상기 Ar1, R1 및 R2는 각각 독립적으로 페닐기, 비페닐기 또는 나프틸기인 화합물.
According to paragraph 1,
A compound wherein Ar1, R1, and R2 are each independently a phenyl group, a biphenyl group, or a naphthyl group.
 제1항에 있어서,
상기 L1은 페닐렌, 비페닐렌, 터페닐렌 및 이들의 조합인 화합물.
According to paragraph 1,
wherein L1 is phenylene, biphenylene, terphenylene, or a combination thereof.
 제1항에 있어서,
상기 L1 내지 L3중 하나 이상은 메타페닐렌 또는 오쏘페닐렌을 포함하는 화합물.
According to paragraph 1,
A compound wherein at least one of L1 to L3 includes metaphenylene or orthophenylene.
 제1항에 있어서,
상기 L2는 C3~C12의 아릴렌기 또는 C2~C12의 헤테로아릴렌기인 화합물.
According to paragraph 1,
The compound wherein L2 is a C3 to C12 arylene group or a C2 to C12 heteroarylene group.
 제1항에 있어서,
상기 L2는 직접결합 또는 페닐렌인 화합물.
According to paragraph 1,
The compound wherein L2 is a direct bond or phenylene.
 제1항에 있어서,
상기 Ar1은 페닐, 비페닐, 터페닐, 나프틸, 페난트렌, 트리페닐렌, 디메틸플루오렌, 디페닐플루오렌, 스파이로비플루오렌, 디벤조퓨란, 디벤조티오펜, 카바졸, 상기 <화학식1-1> 및 이들의 조합으로 이루어진 군에서 선택되는 화합물.
According to paragraph 1,
Ar1 is phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, triphenylene, dimethylfluorene, diphenylfluorene, spirobifluorene, dibenzofuran, dibenzothiophene, carbazole, the <formula A compound selected from the group consisting of 1-1> and combinations thereof.
 제1항에 있어서,
상기 화합물의 굴절률은 450nm 파장에서 1.70이하인 화합물.
According to paragraph 1,
The compound has a refractive index of 1.70 or less at a wavelength of 450 nm.
 제1항에 있어서,
상기 <화학식1-1>은 하기 화학 구조식 A-1 내지 A-35 중에서 선택되는 화합물;





(상기 화학 구조식에서, R8은 각각 독립적으로 수소, 중수소, 할로겐, 니트로기, 니트릴기, 하이드록시기, 티올기, 치환 또는 비치환된 아미노기, 치환 또는 비치환된 C1~C50의 알킬기, 치환 또는 비치환된 C2~C50의 알케닐기, 치환 또는 비치환된 C1~C50의 알콕시기, 치환 또는 비치환된 C1~C50의 설파이드기, 치환 또는 비치환된 C0~C50의 실릴기, 치환 또는 비치환된 C3~C50의 사이클로알킬기, 치환 또는 비치환된 C3~C50의 사이클로알케닐기, 치환 또는 비치환된 C1~C50의 헤테로사이클릴기, 치환 또는 비치환된 C3~C50의 아릴기, 또는 치환 또는 비치환된 C2~C50의 헤테로아릴기이며,
u는 각각 독립적으로 구조적으로 허용되는 범위내에서 0 내지 10의 정수이고, 구체적으로 0 내지 4의 정수이며,
*는 결합위치를 나타낸다).
According to paragraph 1,
The <Formula 1-1> is a compound selected from the following chemical structures A-1 to A-35;





(In the above chemical structural formula, R8 is each independently hydrogen, deuterium, halogen, nitro group, nitrile group, hydroxy group, thiol group, substituted or unsubstituted amino group, substituted or unsubstituted alkyl group of C1 to C50, substituted or Unsubstituted C2~C50 alkenyl group, substituted or unsubstituted C1~C50 alkoxy group, substituted or unsubstituted C1~C50 sulfide group, substituted or unsubstituted C0~C50 silyl group, substituted or unsubstituted A cycloalkyl group on C3~C50, a substituted or unsubstituted cycloalkenyl group on C3~C50, a substituted or unsubstituted heterocyclyl group on C1~C50, a substituted or unsubstituted aryl group on C3~C50, or substituted or unsubstituted It is a ringed C2~C50 heteroaryl group,
u is each independently an integer from 0 to 10 within a structurally acceptable range, and specifically an integer from 0 to 4,
* indicates the binding position).
 제1항에 있어서,
상기 화학식 1의 화합물이 하기 화학식으로 표현되는 화합물 중 어느 하나인 화합물;












































































.
According to paragraph 1,
A compound in which the compound of Formula 1 is any one of the compounds represented by the following formula;












































































.
 제1항 내지 제14항 중 어느 한 항의 화합물을 포함하는 유기 발광 소자.
An organic light-emitting device comprising the compound of any one of claims 1 to 14.
 제15항에 있어서,
상기 유기 발광 소자는,
제1전극;
제2 전극; 및
상기 제1 전극과 제2 전극의 내측에 개재되는 1층 이상의 유기물층을 포함하며,
상기 유기물층 중 하나 이상의 유기물층은 상기 화합물을 함유하는 유기 발광 소자.
According to clause 15,
The organic light emitting device,
first electrode;
second electrode; and
It includes one or more organic layers interposed inside the first electrode and the second electrode,
An organic light emitting device wherein at least one of the organic material layers contains the compound.
 제16항에 있어서,
상기 화합물은 정공주입층, 정공수송층 및 발광보조층 중 어느 하나 이상의 유기물층에 포함되는 유기 발광 소자.
According to clause 16,
The compound is an organic light-emitting device included in one or more organic material layers among a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer.
 제17항에 있어서,
상기 화합물은 정공주입층 및 정공수송층에 모두 포함되는 유기 발광 소자.According to clause 17,
An organic light emitting device in which the compound is included in both the hole injection layer and the hole transport layer.
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