KR20210133882A - Novel compound and organic electroluminescent device comprising the same - Google Patents
Novel compound and organic electroluminescent device comprising the same Download PDFInfo
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- KR20210133882A KR20210133882A KR1020210054862A KR20210054862A KR20210133882A KR 20210133882 A KR20210133882 A KR 20210133882A KR 1020210054862 A KR1020210054862 A KR 1020210054862A KR 20210054862 A KR20210054862 A KR 20210054862A KR 20210133882 A KR20210133882 A KR 20210133882A
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H01L51/0052—
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- H01L51/006—
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- H01L51/5056—
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- H01L51/5088—
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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Abstract
Description
본 발명은 신규 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다. The present invention relates to a novel compound and an organic light emitting device comprising the same.
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, a self-luminous organic light-emitting device capable of low-voltage driving has superior viewing angle and contrast ratio, and does not require a backlight, compared to a liquid crystal display (LCD), which is the mainstream of flat panel display devices. It is also advantageous in terms of power consumption and has a wide color reproduction range, attracting attention as a next-generation display device.
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 may be classified into light emitting layer materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials, and the like, according to their functions.
그리고 상기 발광 재료는 분자량에 따라 고분자과 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 material can be classified into polymers and monomolecules according to molecular weight. According to the light emission mechanism, fluorescent materials derived from singlet excited states of electrons, phosphorescent materials derived from triplet excited states of electrons, and triplet excited states. It can be classified as a delayed fluorescence material from which the movement of electrons in a singlet excited state is derived, and the light emitting material can be divided into blue, green, and red light emitting materials and yellow and orange light emitting materials necessary to realize a better natural color according to the emission color. can
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. In addition, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system may be used as a light emitting material. The principle is that the energy band gap is smaller than that of the host, and when a small amount of dopant, which is a light emitting material, is mixed in the light emitting layer, excitons generated in the host are transferred to the dopant to emit light. Using this principle, it is possible to obtain light of a desired wavelength 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.Until now, 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, development of new materials is continuously required due to high driving voltage, low efficiency, and short lifespan. Accordingly, efforts have been made to develop an organic light emitting device having low voltage driving, high luminance, and long lifespan using a material having excellent properties.
본 발명은 깊은 HOMO 형성과 파이컨쥬게이션 증가로 인해 박막형성 시 분자 배열이 우수하고 빠른 홀 모빌리티를 가질 수 있는 신규 화합물 및 유기 발광 소자를 제공하는 것을 목적으로 한다.An object of the present invention is to provide a novel compound and an organic light emitting device capable of having excellent molecular arrangement and fast hole mobility when forming a thin film due to deep HOMO formation and increased pi-conjugation.
또한, 높은 LUMO 및 T1을 가짐에 따라 발광층 내 엑시톤의 이동 차단 효과가 극대화되어 고효율을 구현할 수 있고, 롤오프 현상 억제를 통한 장수명 효과를 구현할 수 있는 신규 화합물 및 유기 발광 소자를 제공하는 것을 목적으로 한다.In addition, as it has high LUMO and T1, the effect of blocking the movement of excitons in the light emitting layer is maximized to realize high efficiency, and to provide a novel compound and an organic light emitting device that can implement a long life effect by suppressing the roll-off phenomenon. .
또한, 플루오렌 모이어티와 오쏘 연결기 확장을 통하여 높은 Tg를 가짐에 따라, 박막의 재결정화를 방지할 수 있고 이를 통해 구동 안정성을 향상시킬 수 있는 신규 화합물 및 유기 발광 소자를 제공하는 것을 목적으로 한다.In addition, an object of the present invention is to provide a novel compound and an organic light emitting device capable of preventing recrystallization of a thin film and improving driving stability through it having a high Tg through expansion of a fluorene moiety and an ortho linking group. .
상기의 과제 및 추가적 과제에 대하여 아래에서 자세히 서술한다.The above tasks and additional tasks will be described in detail below.
상기 과제를 해결하기 위한 수단으로서,As a means for solving the above problem,
본 발명은 일실시예로서, 하기 화학식 1로 표현되는 화합물을 제공한다.As an embodiment, the present invention provides a compound represented by the following formula (1).
<화학식 1><Formula 1>
상기 화학식 1에서, In Formula 1,
Ar1은 치환 또는 비치환된 C6~C50의 아릴렌기, 또는 치환 또는 비치환된 C5~C50의 헤테로아릴렌기이고,Ar1 is a substituted or unsubstituted C6~ C50 arylene group, or a substituted or unsubstituted C5~ C50 heteroarylene group,
Ar2는 치환 또는 비치환된 C6~C50의 아릴기, 또는 치환 또는 비치환된 C5~C50의 헤테로아릴기이고,Ar2 is a substituted or unsubstituted C6~ C50 aryl group, or a substituted or unsubstituted C5~ C50 heteroaryl group,
L1은 직접결합, 치환 또는 비치환된 C6~C50의 아릴렌기, 또는 치환 또는 비치환된 C2~C50의 헤테로아릴렌기이고,L1 is a direct bond, a substituted or unsubstituted C6~ C50 arylene group, or a substituted or unsubstituted C2~ C50 heteroarylene group,
R, R` 및 R``는 각각 독립적으로 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 C3~C30의 실릴기, 치환 또는 비치환된 C6~C50의 아릴기, 또는 치환 또는 비치환된 C2~C50의 헤테로아릴기이며, R` 및 R``는 서로 결합하여 환을 형성하거나 형성하지 않을 수 있으며,R, R` and R`` are each independently hydrogen, deuterium, halogen, nitro group, nitrile group, substituted or unsubstituted C1~ C30 alkyl group, substituted or unsubstituted C2~ C30 alkenyl group, substituted or unsubstituted A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 sulfide group, a substituted or unsubstituted C3 to C30 silyl group, a substituted or unsubstituted C6 to C50 aryl group, or a substituted or unsubstituted is a C2~ C50 heteroaryl group, and R` and R`` may or may not form a ring by combining with each other,
R1 내지 R5는 각각 독립적으로 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 C3~C30의 실릴기, 치환 또는 비치환된 C6~C50의 아릴기, 또는 치환 또는 비치환된 C2~C50의 헤테로아릴기이며, 인접한 R1끼리, R2끼리, R3끼리, R4끼리, R5끼리 각각 결합하여 환을 형성할 수 있으며,R1 to R5 are each independently 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-C30 of an alkoxy group, a substituted or unsubstituted C1~ C30 sulfide group, a substituted or unsubstituted C3~ C30 silyl group, a substituted or unsubstituted C6~ C50 aryl group, or a substituted or unsubstituted C2~ C50 group It is a heteroaryl group, and adjacent R 1 , R 2 , R 3 , R 4 , R 5 may be bonded to each other to form a ring,
l, n, o 및 p는 각각 독립적으로 0 내지 4의 정수이며,l, n, o and p are each independently an integer of 0 to 4,
m은 0 내지 3의 정수이다.m is an integer from 0 to 3.
본 발명에 따른 화합물 및 유기 발광 소자는, 플루오렌과 플루오렌 9번 위치 오쏘 확장된 연결기를 통하여 아릴아민의 질소에 결합된 구조로, 깊은 HOMO 형성과 파이컨쥬게이션 증가로 인해 박막형성 시 분자배열이 우수하고 빠른 홀 모빌리티를 가질 수 있다.The compound and the organic light emitting device according to the present invention have a structure bonded to nitrogen of arylamine through fluorene and an ortho-extended linker at the 9th position of fluorene, and molecular arrangement during thin film formation due to deep HOMO formation and increased pi-conjugation It can have excellent and fast hall mobility.
또한, 높은 LUMO 및 T1을 가짐에 따라 발광층 내 엑시톤의 이동 차단 효과가 극대화되어 고효율을 구현할 수 있고, 롤오프 현상 억제를 통한 장수명 효과를 가지는 유기 발광 소자를 구현할 수 있다. In addition, by having high LUMO and T1, the effect of blocking the movement of excitons in the light emitting layer is maximized, so that high efficiency can be realized, and an organic light emitting device having a long lifespan effect through suppression of the roll-off phenomenon can be realized.
또한, 플루오렌 모이어티와 오쏘 연결기 확장을 통한 높은 Tg를 가짐에 따라, 박막의 재결정화 방지를 통한 구동 안정성이 뛰어난 유기 발광 소자를 구현할 수 있다. In addition, since it has a high Tg through the expansion of the fluorene moiety and the ortho linker, an organic light emitting device having excellent driving stability by preventing recrystallization of the thin film can be realized.
상기의 효과 및 추가적 효과에 대하여 아래에서 자세히 서술한다.The above effects and additional effects will be 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 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.Prior to describing the present invention in detail below, it is to be understood that the terminology used herein is for the purpose of describing specific embodiments and is not intended to limit the scope of the present invention, which is limited only by the appended claims. shall. All technical and scientific terms used herein have the same meanings as commonly understood by those of ordinary skill in the art, unless otherwise stated.
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 stated otherwise, the term comprise, comprises, comprising is meant to include the stated object, step or group of objects, and steps, and any other object. It is not used in the sense of excluding steps or groups of objects or groups 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 의미할 수 있으며, "헤테로아릴"은 1 개 이상의 헤테로 원소를 포함하는 C2-50의 방향족 고리로서, 예를 들어, 피롤릴, 피라지닐, 피리디닐, 인돌릴, 이소인돌릴, 푸릴, 벤조푸라닐, 이소벤조푸라닐, 디벤조푸라닐, 벤조티오페닐, 디벤조티오페닐, 퀴놀릴기, 이소퀴놀릴, 퀴녹살리닐, 카르바졸릴, 페난트리디닐, 아크리디닐, 페난트롤리닐, 티에닐, 및 피리딘 고리, 피라진 고리, 피리미딘 고리, 피리다진 고리, 트리아진 고리, 인돌 고리, 퀴놀린 고리, 아크리딘고리, 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 may be meant to include an aromatic ring such as renyl, perylenyl, chrysenyl, fluoranthenyl, benzofluorenyl, benzotriphenylenyl, benzochrysenyl, anthracenyl, stilbenyl, pyrenyl, and the like; "Aryl" is a C2-50 aromatic ring containing one or more heteroatoms, for example, pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindolyl, furyl, benzofuranyl, isobenzofuranyl, Dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, quinolyl group, isoquinolyl, quinoxalinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, thienyl, and pyridine ring, pyrazine Ring, pyrimidine 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 , may mean including a heterocyclic group formed from a dibenzofuran ring and the like.
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, R x(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 formula, Ar x (where x is an integer) means a substituted or unsubstituted C6-C50 aryl group, or a substituted or unsubstituted C2-C50 heteroaryl group, unless otherwise defined, and L x ( Here, x is an integer) is a direct bond, a substituted or unsubstituted C6~ C50 arylene group, or a substituted or unsubstituted C2~C50 heteroarylene group, unless otherwise defined, and R x (where x is integer) is 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 ~ C30 alkoxy group, substituted or unsubstituted C1~ C30 sulfide group, substituted or unsubstituted C6~ C50 aryl group, or 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, 또는 C1~C30의 알킬기, C1~C30의 알킬술피닐기, C1~C30의 알킬술포닐기, C1~C30의 알킬술파닐기, C1∼C12 의 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, C3~C30의 실릴기, C3~C20의 시클로알킬기, C3~C20의 헤테로시클로알킬기, C6~C50의 아릴기 및 C2~C50의 헤테로아릴기 등으로 이루어진 군으로부터 선택된 하나 이상의 기로 치환되거나 치환되지 않는 것을 의미할 수 있으나, 특별히 이에 한정되는 것은 아니다. 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, 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-alkylsulfamoyl group, C2 to C12 N,N-dialkylsulfamoyl group, C3 to C30 silyl group, C3 to C20 cycloalkyl group, C3 to C20 heterocycloalkyl group, C6 to C50 aryl group and C2 to C50 heteroaryl group It may mean unsubstituted or substituted with one or more groups selected from the group consisting of, but is not particularly limited thereto. In addition, the same symbols throughout the present 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.On the other hand, 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.
이하에서 본 발명을 상세히 설명한다. Hereinafter, the present invention will be described in detail.
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>
상기 화학식 1에서, In Formula 1,
Ar1은 치환 또는 비치환된 C6~C50의 아릴렌기, 또는 치환 또는 비치환된 C5~C50의 헤테로아릴렌기이고,Ar1 is a substituted or unsubstituted C6~ C50 arylene group, or a substituted or unsubstituted C5~ C50 heteroarylene group,
Ar2는 치환 또는 비치환된 C6~C50의 아릴기, 또는 치환 또는 비치환된 C5~C50의 헤테로아릴기이고,Ar2 is a substituted or unsubstituted C6~ C50 aryl group, or a substituted or unsubstituted C5~ C50 heteroaryl group,
L1은 직접결합, 치환 또는 비치환된 C6~C50의 아릴렌기, 또는 치환 또는 비치환된 C2~C50의 헤테로아릴렌기이고,L1 is a direct bond, a substituted or unsubstituted C6~ C50 arylene group, or a substituted or unsubstituted C2~ C50 heteroarylene group,
R, R` 및 R``는 각각 독립적으로 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 C3~C30의 실릴기, 치환 또는 비치환된 C6~C50의 아릴기, 또는 치환 또는 비치환된 C2~C50의 헤테로아릴기이며, R` 및 R``는 서로 결합하여 환을 형성하거나 형성하지 않을 수 있으며,R, R` and R`` are each independently hydrogen, deuterium, halogen, nitro group, nitrile group, substituted or unsubstituted C1~ C30 alkyl group, substituted or unsubstituted C2~ C30 alkenyl group, substituted or unsubstituted A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 sulfide group, a substituted or unsubstituted C3 to C30 silyl group, a substituted or unsubstituted C6 to C50 aryl group, or a substituted or unsubstituted is a C2~ C50 heteroaryl group, and R` and R`` may or may not form a ring by combining with each other,
R1 내지 R5는 각각 독립적으로 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 C3~C30의 실릴기, 치환 또는 비치환된 C6~C50의 아릴기, 또는 치환 또는 비치환된 C2~C50의 헤테로아릴기이며, 인접한 R1끼리, R2끼리, R3끼리, R4끼리, R5끼리 각각 결합하여 환을 형성하거나 형성하지 않을 수 있으며,R1 to R5 are each independently 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-C30 of an alkoxy group, a substituted or unsubstituted C1~ C30 sulfide group, a substituted or unsubstituted C3~ C30 silyl group, a substituted or unsubstituted C6~ C50 aryl group, or a substituted or unsubstituted C2~ C50 group It is a heteroaryl group, and adjacent R 1 , R 2 , R 3 , R 4 , and R 5 may be bonded to each other to form a ring or not,
l, n, o 및 p는 각각 독립적으로 0 내지 4의 정수이며,l, n, o and p are each independently an integer of 0 to 4,
m은 0 내지 3의 정수이다.m is an integer from 0 to 3.
상기에서, 치환되는 경우 치환기는 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 헤테로아릴기일 수 있다.In the above, when substituted, the substituent is deuterium, halogen, nitro group, nitrile group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C2-C30 alkenyl group, substituted or unsubstituted C1-C30 It may be an 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.
상기와 같이 화학식 1로 표현되는 본 발명의 화합물은 플루오렌과 플루오렌9번 위치 오쏘 확장된 연결기를 통하여 아릴아민의 질소에 결합된 구조로, 발광보조층에 적합한 깊은 HOMO 형성과 파이컨쥬게이션 증가로 인해 박막형성 시 분자배열이 우수하고 빠른 홀 모빌리티를 가질 수 있다. 또한, 높은 LUMO 및 T1 을 가짐에 따라 발광층 내 엑시톤의 이동 차단 효과가 극대화되어, 고효율을 구현할 수 있고, 롤오프 현상 억제를 통한 장수명 효과를 가지는 유기 발광 소자를 구현할 수 있다. 또한, 플루오렌 모이어티와 오쏘 연결기 확장을 통한 높은 Tg를 가짐에 따라, 박막의 재결정화를 방지할 수 있고 이를 통해 구동 안정성이 뛰어난 유기 발광 소자를 구현할 수 있다. As described above, the compound of the present invention represented by Chemical Formula 1 has a structure bonded to the nitrogen of arylamine through an ortho-extended linking group at the 9th position of fluorene and fluorene, and forms a deep HOMO suitable for a light-emitting auxiliary layer and increases pi-conjugation Therefore, when forming a thin film, the molecular arrangement is excellent and it can have fast hole mobility. In addition, by having high LUMO and T1, the effect of blocking the movement of excitons in the light emitting layer is maximized, so that high efficiency can be realized, and an organic light emitting device having a long lifespan effect through suppression of the roll-off phenomenon can be realized. In addition, since it has a high Tg through the expansion of the fluorene moiety and the ortho linking group, recrystallization of the thin film can be prevented and an organic light emitting device having excellent driving stability can be realized.
더 구체적으로는, 상기 화학식 1은 하기 화학식 2로 표현될 수 있다.More specifically, Chemical Formula 1 may be represented by Chemical Formula 2 below.
<화학식 2><Formula 2>
상기 화학식 2에서, In Formula 2,
Ar2, R, R`, R``, R1 내지 R5, l, n, o, p, 및 m은 상기 화학식 1에서의 정의와 동일하며, R6는 상기 R1의 정의와 동일하며, q는 1 내지 4의 정수이며, u는 0 내지 4의 정수이다.Ar2, R, R`, R``, R1 to R5, l, n, o, p, and m are the same as defined in Formula 1 above, R6 is the same as defined in R1, and q is 1 to It is an integer of 4, and u is an integer of 0-4.
상기 화학식 2의 화합물은 화학식 1에서 Ar1이 1개 이상의 페닐렌으로 이루어져있고, L1이 직접결합인 구조로, 높은 LUMO를 가짐과 동시에 높은 T1을 형성하여, 발광층 내 엑시톤의 이동 차단에 효과적일 수 있다.The compound of Formula 2 has a structure in which Ar1 consists of one or more phenylenes in Formula 1 and L1 is a direct bond, has a high LUMO and at the same time forms a high T1, so it can be effective in blocking the movement of excitons in the light emitting layer have.
또한, 상기 화학식 1은 구체적으로 하기 화학식 3으로 표현될 수 있다. In addition, Chemical Formula 1 may be specifically represented by Chemical Formula 3 below.
<화학식 3><Formula 3>
상기 화학식 3에서,In Formula 3,
Ar2, R`, R``, R1 내지 R5, l, n, o, p, 및 m은 상기 화학식 1에서의 정의와 동일하며,Ar2, R`, R``, R1 to R5, l, n, o, p, and m are the same as defined in Formula 1 above,
Ar은 상기 Ar2의 정의와 동일하다.Ar has the same definition as Ar2 above.
상기 화학식 3의 화합물은 화학식 1에서의 R이 Ar즉, 아릴기 또는 헤테로아릴기로 이루어지고, L1이 직접결합이며, 페닐 플루오렌의 9번 위치의 페닐이 치환기가 존재하지 않음으로써, 더욱이 깊은 호모를 유지하고, 연결기의 뒤틀림을 최소화로 빠른 모빌리티를 유지하여, 발광층내 전하의 균형을 용이하게 하여, 효율 및 수명 개선에 유리할 수 있다.In the compound of Formula 3, R in Formula 1 is Ar, that is, consisting of an aryl group or a heteroaryl group, L1 is a direct bond, and the phenyl at the 9th position of phenyl fluorene does not have a substituent, so that further deep homo It can be advantageous for improving efficiency and lifespan by facilitating the balance of electric charges in the light emitting layer by maintaining fast mobility by minimizing distortion of the connector.
한편, 상기 화학식 3은 하기 화학식 3-1으로 표현될 수도 있다.Meanwhile, Chemical Formula 3 may be represented by the following Chemical Formula 3-1.
<화학식 3-1><Formula 3-1>
상기 화학식 3-1에서,In Formula 3-1,
Ar2, R`, R``, R1 내지 R5, l, n, o, p, m, 및 Ar은 상기 화학식 3에서의 정의와 동일하다.Ar2, R', R'', R1 to R5, l, n, o, p, m, and Ar are the same as defined in Formula 3 above.
상기 화학식 3-1의 화합물은 화학식 3에서 페닐 플루오렌의 9번 위치의 페닐에 H가 결합된 구조로, H가 결합된 위치가 블록킹(blocking)되어 플루오렌이 오쏘가 아닌 파라 또는 메타로만 결합될 수 있도록 함으로써, 연결기의 뒤틀림을 최소화하여 박막배열이 우수하고, 빠른 모빌리티를 유지할 수 있다.The compound of Formula 3-1 has a structure in which H is bonded to phenyl at position 9 of phenyl fluorene in Formula 3, and the position to which H is bonded is blocked, so that fluorene is only bonded to para or meta, not ortho By making it possible, the distortion of the connector is minimized, so that the thin film arrangement is excellent, and fast mobility can be maintained.
또한, 상기 화학식 1은 구체적으로 하기 화학식 4로 표현될 수 있다. In addition, Chemical Formula 1 may be specifically represented by Chemical Formula 4 below.
<화학식 4><Formula 4>
상기 화학식 4에서,In Formula 4,
Ar2, R`, R``, R1 내지 R5, l, n, o, p, 및 m은 상기 화학식 1에서의 정의와 동일하며,Ar2, R`, R``, R1 to R5, l, n, o, p, and m are the same as defined in Formula 1 above,
R7은 상기 R1의 정의와 동일하며,R7 is the same as the definition of R1 above,
v는 0 내지 5의 정수이다.v is an integer from 0 to 5;
상기 화학식 4의 화합물은 일측 플루오렌의 2번 위치에 아민이 직접 결합하고, 타측 플루오렌이 디페닐플루오렌으로 이루어져, 발광보조층에 용이한 HOMO 및 홀 모빌리티 개선에 효과적이므로 높은 효율을 유지하며, 롤오프현상 억제를 통한 수명 개선에 효과적일 수 있다.In the compound of Formula 4, the amine is directly bonded to the 2nd position of the fluorene on one side and the fluorene on the other side is made of diphenylfluorene, so it is effective in improving HOMO and hole mobility easily in the light emitting auxiliary layer, so it maintains high efficiency. , it can be effective in improving the lifespan by suppressing the roll-off phenomenon.
한편, 상기 화학식 4는 하기 화학식 4-1로 표현될 수 있다.Meanwhile, Chemical Formula 4 may be represented by the following Chemical Formula 4-1.
<화학식 4-1><Formula 4-1>
상기 화학식 4-1에서,In Formula 4-1,
Ar2, R`, R``, R1 내지 R5, 및 R7 은 상기 화학식 4에서의 정의와 동일하다.Ar2, R`, R``, R1 to R5, and R7 are the same as defined in Formula 4 above.
상기 화학식 4-1의 화합물은 화학식4에서 디페닐 플루오렌의 9번 위치의 페닐에 H가 결합된 구조로, H가 결합된 위치가 블록킹(blocking)되어 플루오렌이 오쏘가 아닌 파라 또는 메타로만 결합될 수 있도록 함으로써, 연결기의 뒤틀림을 최소화하여 박막배열이 우수하고, 빠른 모빌리티를 유지할 수 있다.The compound of Formula 4-1 has a structure in which H is bonded to phenyl at position 9 of diphenyl fluorene in Formula 4, and the position to which H is bonded is blocked so that fluorene is not ortho, but only para or meta. By making it possible to be coupled, it is possible to minimize distortion of the connector, thereby providing excellent thin film arrangement and maintaining fast mobility.
또한, 상기 화학식 1 내지 화학식 4에서, 상기 R, R`, R``, R1 내지 R7은 각각 독립적으로 수소, 중수소, 메틸기, 또는 페닐기일 수 있다. 이를 통해, 분자의 벌키특성을 최소화하여 모빌리티 저하를 억제할 수 있어, 구동전압 개선에 효과적임과 동시에 낮은 증착온도로 인해 열 안정성이 뛰어날 수 있다.In addition, in Formulas 1 to 4, R, R`, R``, and R1 to R7 may each independently be hydrogen, deuterium, a methyl group, or a phenyl group. Through this, it is possible to suppress the decrease in mobility by minimizing the bulky characteristic of the molecule, so that it is effective in improving the driving voltage, and at the same time, the thermal stability may be excellent due to the low deposition temperature.
또한, 상기 화학식 1 내지 화학식 4에서, 상기 R` 및 R``은 메틸기일 수 있다. 이를 통해, 플루오렌의 벌키특성을 최소화하고 빠른 홀 모빌리티를 가져 구동전압 개선에 효과적임과 롤오프현상 억제를 통한 수명개선에 효과적일 수 있다.In addition, in Formulas 1 to 4, R` and R`` may be a methyl group. Through this, it can be effective in improving the driving voltage by minimizing the bulky characteristic of fluorene and having fast hall mobility and improving the lifespan by suppressing the roll-off phenomenon.
또한, 상기 화학식 1 내지 화학식 4에서, Ar2는 페닐, 나프틸, 비페닐, 터페닐, 페난트렌일, 트리페닐렌일, 디메틸플루오렌, 디페닐플루오렌, 스파이로비플루오렌, 디벤조퓨란, 디벤조티오펜, 카바졸 및 이들의 조합으로 이루어진 군에서 선택될 수 있으며, 구체적으로 페닐, 나프틸, 비페닐, 디벤조퓨란, 디벤조티오펜 또는 이들의 조합으로 이루어진 군에서 선택된 것일 수 있다. 더욱 구체적으로 페닐, 나프틸, 비페닐일 수 있다. 이를 통해 높은 LUMO 및 T1을 형성 할 수 있어, 효율 개선에 효과적이고 동시에 증착 온도를 낮출 수 있어 열 안정성에 유리할 수 있다.In addition, in Formulas 1 to 4, Ar2 is phenyl, naphthyl, biphenyl, terphenyl, phenanthrenyl, triphenylenyl, dimethylfluorene, diphenylfluorene, spirobifluorene, dibenzofuran, di It may be selected from the group consisting of benzothiophene, carbazole, and combinations thereof, and specifically, it may be selected from the group consisting of phenyl, naphthyl, biphenyl, dibenzofuran, dibenzothiophene, or a combination thereof. More specifically, it may be phenyl, naphthyl, or biphenyl. Through this, high LUMO and T1 can be formed, which is effective for improving efficiency and at the same time lowering the deposition temperature, which can be advantageous for thermal stability.
아래의 화합물들은 본 발명에 따른 화합물의 구체적인 예들이다. 하기의 예들은 본 발명을 설명하기 위한 예시일 뿐이므로, 본 발명이 이에 한정되는 것은 아니다. The following compounds are specific examples of the compounds according to the present invention. Since the following examples are only examples for explaining the present invention, the present invention is not limited thereto.
한편, 본 발명은 또 다른 일실시예로서 상기 화학식 1로 표시되는 화합물을 포함하는 유기 발광 소자를 제공한다. 상기 유기 발광 소자는 제 1 전극 및 제 2 전극 사이에 본 발명에 따른 화합물을 포함하는 1층 이상의 유기물층을 포함할 수 있다.Meanwhile, as another embodiment, the present invention provides an organic light emitting device including the compound represented by Formula 1 above. The organic light emitting device may include one or more organic material layers including the compound according to the present invention between the first electrode and the second electrode.
본 발명의 일실시예에 있어서, 상기 유기물층은 정공주입층, 정공수송층 및 발광보조층 중 1층 이상일 수 있으며, 예를 들어 발광보조층일 수 있으나, 이에 제한되지 않을 수 있으며, 이때, 본 발명의 화합물은 단독으로 사용되거나 공지의 유기발광 화합물과 함께 사용될 수 있다.In one embodiment of the present invention, the organic material layer may be one or more of a hole injection layer, a hole transport layer, and a light emission auxiliary layer, for example, may be a light emission auxiliary layer, but may not be limited thereto. The compound may be used alone or in combination with a known organic light emitting compound.
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.Specifically, the organic light emitting device of the present invention includes a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL), an electron injection layer (EIL) between the first electrode and the second electrode. One or more organic material layers may be included.
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) 순으로 적층되어 제조될 수 있다. As shown in FIG. 1 , the organic light emitting device of the present invention has 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 from below. , the electron transport layer 500 , the electron injection layer 600 , and the second electrode (electron injection electrode, 2000) may be stacked in this 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) 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.In addition, 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 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, and in particular, a transparent glass substrate or a flexible plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness. have.
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 of the organic light emitting diode. A material having a low work function is used to allow hole injection, and may be formed of a transparent material such as indium tin oxide (ITO), indium zinc oxide (IZO), or 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 first electrode by a method such as a vacuum deposition method, a spin coating method, a casting method, or a Langmuir-Blodgett (LB) method. In the case of forming the hole injection layer by the vacuum deposition method, the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal characteristics of the desired hole injection layer, etc., 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 μm may 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 may be formed by depositing a hole transport layer material on the hole injection layer 200 by a method such as a vacuum deposition method, a spin coating method, a casting method, a LB method, or the like. In the case of forming the hole transport layer by the vacuum deposition method, the deposition conditions vary depending on the compound used, but in general, it is preferable to select the hole transport layer within the same range of conditions as those for the hole injection layer formation. The hole transport layer may be one or more, for example, may be two layers of a first hole transport layer and a second hole transport layer (emission 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 may be formed by depositing the light emitting layer material on the hole transport layer or the light emitting auxiliary layer by a method such as a vacuum deposition method, a spin coating method, a casting method, a LB method, or the like. In the case of forming the light emitting layer by the vacuum deposition method, the deposition conditions vary depending on the compound used, but in general, it is preferable to select the light emitting layer within the same range of conditions as those for the formation of the hole injection layer. In addition, as the light emitting layer material, a known compound may be used as a host or a 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 together with a phosphorescent dopant in the light emitting layer, a hole blocking material (HBL) may be additionally laminated by vacuum deposition or spin coating to prevent triplet excitons or holes from diffusing into the electron transport layer. In this case, the hole-blocking material that can be used is not particularly limited, and any one can be used by selecting from known materials used as the hole-blocking material. For example, an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, or a hole-inhibiting material described in Japanese Patent Application Laid-Open No. Hei 11-329734 (A1), etc. are mentioned. Representatively, Balq (bis(8-hydr) hydroxy-2-methylquinolinol nato)-aluminum biphenoxide), phenanthrolines-based compounds (eg, UDC's BCP (vasocuproin)), and the like may 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.The electron transport layer 500 is formed on the light emitting layer 400 formed as described above. In this case, the electron transport layer may be formed by a method such as a vacuum deposition method, a spin coating method, a casting method, or the like. In addition, although the deposition conditions of the electron transport layer vary depending on the compound used, in general, it is preferable to select the electron transport layer within the same range of conditions as those for the formation of 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.Then, the electron injection layer 600 may be formed by depositing an electron injection layer material on the electron transport layer 500, wherein the electron injection layer is a conventional electron injection layer material by vacuum deposition, spin coating, It can form by methods, such as a casting method.
상기 유기 발광 소자의 정공주입층(200), 정공수송층(300), 발광층(400), 전자수송층(500)는 본 발명에 따른 화합물을 사용하거나 하기 표 1과 같은 물질을 사용할 수 있으며, 또는 본 발명에 따른 화합물과 공지의 물질을 함께 사용할 수 있다.The hole injection layer 200, the hole transport layer 300, the light emitting layer 400, and the electron transport layer 500 of the organic light emitting device may use a compound according to the present invention or a material shown in Table 1 below, or The compound according to the invention and a known substance may be used together.
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 a vacuum deposition method or a sputtering method. 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 an organic light emitting device having 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) structure as well as an organic light emitting device having various structures. structure is possible, and it is also possible to further form an intermediate layer of one or two layers, if necessary.
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 material layer formed according to the present invention can be adjusted according to the required degree, and is preferably 10 to 1,000 nm, 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, in the present invention, the organic material layer including the compound represented by Formula 1 has a uniform surface and excellent shape stability because the thickness of the organic material layer can be adjusted in molecular units.
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 a synthesis example of a compound according to an embodiment of the present invention and an organic light emitting device manufacturing example. The following examples only illustrate the present invention, but the scope of the present invention is not limited to the following examples.
<< 제조예manufacturing example 1> 화합물 7의 합성 1> Synthesis of compound 7
둥근바닥플라스크에 9-(2'-bromo-[1,1'-biphenyl]-4-yl)-9-phenyl-9H-fluorene 3.0g, 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine 1.8g, t-BuONa 0.9g, Pd2(dba)3 0.2g, (t-Bu)3P 0.3ml를 톨루엔 80ml에 녹인 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결하였다. 유기층을 MC로 추출하고 감압여과한 후 컬럼정제 및 재결정하여 화합물 7 3.0g (수율 70%)을 얻었다.9-(2'-bromo-[1,1'-biphenyl]-4-yl)-9-phenyl-9H-fluorene 3.0 g, 9,9-dimethyl-N-phenyl-9H-fluoren- in a round bottom flask 2-amine 1.8 g, t-BuONa 0.9 g, Pd 2 (dba) 3 0.2 g, (t-Bu) 3 P 0.3 ml was dissolved in 80 ml toluene and stirred under reflux. The reaction was confirmed by TLC, and the reaction was terminated after addition of water. The organic layer was extracted with MC, filtered under reduced pressure, and purified by column and recrystallized to obtain 3.0 g of compound 7 (yield 70%).
m/z: 677.31 (100.0%), 678.31 (57.1%), 679.31 (15.7%), 680.32 (2.9%)m/z: 677.31 (100.0%), 678.31 (57.1%), 679.31 (15.7%), 680.32 (2.9%)
<< 제조예manufacturing example 2> 화합물 8의 합성 2> Synthesis of compound 8
제조예 1과 같은 방법으로 제조하되, 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine 대신 N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine을 이용하여 화합물 8을 합성하였다.(수율68%)Prepared in the same manner as in Preparation Example 1, but instead of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl Compound 8 was synthesized using -9H-fluoren-2-amine. (Yield 68%)
m/z: 753.34 (100.0%), 754.34 (63.1%), 755.35 (19.6%), 756.35 (4.0%)m/z: 753.34 (100.0%), 754.34 (63.1%), 755.35 (19.6%), 756.35 (4.0%)
<< 제조예manufacturing example 3> 화합물 10의 합성 3> Synthesis of compound 10
제조예 1과 같은 방법으로 제조하되, 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine 대신 N-([1,1'-biphenyl]-2-yl)-9,9-dimethyl-9H-fluoren-2-amine을 이용하여 화합물 10을 합성하였다.(수율71%)Prepared in the same manner as in Preparation Example 1, except that N-([1,1'-biphenyl]-2-yl)-9,9-dimethyl instead of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine Compound 10 was synthesized using -9H-fluoren-2-amine. (Yield 71%)
m/z: 753.34 (100.0%), 754.34 (63.1%), 755.35 (19.6%), 756.35 (4.0%)m/z: 895.35 (100.0%), 896.35 (73.1%), 897.35 (27.0%), 898.36 (6.2%), 899.36 (1.2%)m/z: 753.34 (100.0%), 754.34 (63.1%), 755.35 (19.6%), 756.35 (4.0%) m/z: 895.35 (100.0%), 896.35 (73.1%), 897.35 (27.0%), 898.36 (6.2%), 899.36 (1.2%)
<< 제조예manufacturing example 4> 화합물 11의 합성 4> Synthesis of compound 11
제조예 1과 같은 방법으로 제조하되, 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine 대신 9,9-dimethyl-N-(naphthalen-1-yl)-9H-fluoren-2-amine을 이용하여 화합물 11을 합성하였다.(수율65%)Prepared in the same manner as in Preparation Example 1, but instead of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine, 9,9-dimethyl-N-(naphthalen-1-yl)-9H-fluoren-2- Compound 11 was synthesized using amine. (Yield 65%)
m/z: 727.32 (100.0%), 728.33 (61.0%), 729.33 (18.3%), 730.33 (3.6%)m/z: 727.32 (100.0%), 728.33 (61.0%), 729.33 (18.3%), 730.33 (3.6%)
<< 제조예manufacturing example 5> 화합물 92의 합성 5> Synthesis of compound 92
제조예 1과 같은 방법으로 제조하되, 9-(2'-bromo-[1,1'-biphenyl]-4-yl)-9-phenyl-9H-fluorene 및 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine 대신 9-(2'-bromo-[1,1'-biphenyl]-3-yl)-9-phenyl-9H-fluorene 및N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine 을 이용하여 화합물 92를 합성하였다.(수율61%)Prepared in the same manner as in Preparation Example 1, but 9-(2'-bromo-[1,1'-biphenyl]-4-yl)-9-phenyl-9H-fluorene and 9,9-dimethyl-N-phenyl- 9-(2'-bromo-[1,1'-biphenyl]-3-yl)-9-phenyl-9H-fluorene and N-([1,1'-biphenyl]- instead of 9H-fluoren-2-amine Compound 92 was synthesized using 4-yl)-9,9-dimethyl-9H-fluoren-2-amine. (Yield 61%)
m/z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)m/z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)
<< 제조예manufacturing example 6> 화합물 259의 합성 6> Synthesis of compound 259
제조예 1과 같은 방법으로 제조하되, 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine 대신 N,9,9-triphenyl-9H-fluoren-2-amine을 이용하여 화합물 259를 합성하였다.(수율68%) Compound 259 was synthesized in the same manner as in Preparation Example 1, but using N,9,9-triphenyl-9H-fluoren-2-amine instead of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine. (yield 68%)
m/z: 801.34 (100.0%), 802.34 (67.4%), 803.35 (22.5%), 804.35 (4.9%)m/z: 801.34 (100.0%), 802.34 (67.4%), 803.35 (22.5%), 804.35 (4.9%)
<< 제조예manufacturing example 7> 화합물 289의 합성 7> Synthesis of compound 289
제조예 1과 같은 방법으로 제조하되, 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine 대신 N-phenyl-9,9'-spirobi[fluoren]-2-amine을 이용하여 화합물 289를 합성하였다.(수율68%) Compound 289 was prepared in the same manner as in Preparation Example 1, but using N-phenyl-9,9'-spirobi[fluoren]-2-amine instead of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine was synthesized. (Yield 68%)
m/z: 799.32 (100.0%), 800.33 (67.5%), 801.33 (22.4%), 802.33 (4.9%)m/z: 799.32 (100.0%), 800.33 (67.5%), 801.33 (22.4%), 802.33 (4.9%)
<< 제조예manufacturing example 8> 화합물 1의 합성 8> Synthesis of compound 1
제조예 1과 같은 방법으로 제조하되, 9-(2'-bromo-[1,1'-biphenyl]-4-yl)-9-phenyl-9H-fluorene 대신 9-(2'-bromo-[1,1'-biphenyl]-4-yl)-9-methyl-9H-fluorene을 이용하여 화합물 1을 합성하였다.(수율58%)Prepared in the same manner as in Preparation Example 1, but 9-(2'-bromo-[1,1'-biphenyl]-4-yl)-9-phenyl-9H-fluorene instead of 9-(2'-bromo-[1) Compound 1 was synthesized using ,1'-biphenyl]-4-yl)-9-methyl-9H-fluorene. (Yield 58%)
m/z: 615.29 (100.0%), 616.30 (51.3%), 617.30 (12.9%), 618.30 (2.1%)m/z: 615.29 (100.0%), 616.30 (51.3%), 617.30 (12.9%), 618.30 (2.1%)
<< 제조예manufacturing example 9> 화합물 434의 합성 9> Synthesis of compound 434
제조예 1과 같은 방법으로 제조하되, 9-(2'-bromo-[1,1'-biphenyl]-4-yl)-9-phenyl-9H-fluorene 대신 9-(2'-bromo-[1,1'-biphenyl]-4-yl)-9-(naphthalen-2-yl)-9H-fluorene을 이용하여 화합물 434를 합성하였다.(수율55%)Prepared in the same manner as in Preparation Example 1, but 9-(2'-bromo-[1,1'-biphenyl]-4-yl)-9-phenyl-9H-fluorene instead of 9-(2'-bromo-[1) Compound 434 was synthesized using ,1'-biphenyl]-4-yl)-9-(naphthalen-2-yl)-9H-fluorene. (Yield 55%)
m/z: 727.32 (100.0%), 728.33 (61.0%), 729.33 (18.3%), 730.33 (3.6%)m/z: 727.32 (100.0%), 728.33 (61.0%), 729.33 (18.3%), 730.33 (3.6%)
<< 실시예Example > : 유기 발광 소자의 제조> : Manufacturing of organic light emitting devices
본 발명의 유기 발광 소자는 아래 표 2에 정리된 물질들을 사용하였다.For the organic light emitting device of the present invention, materials listed in Table 2 below were used.
<< 실시예Example 1> 1>
인듐틴옥사이드(ITO)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 이송 시킨 다음 산소 플라즈마를 이용하여 상기 기판을 5분간 세정 한 후 ITO 기판 상부에 열 진공 증착기(thermal evaporator)를 이용하여 정공주입층 HI01 600Å, HATCN 50 Å, 정공수송층으로 HT01 250 Å, 발광보조층으로 제조예1에서 제조된 화합물 100 Å 을 제막한 후 상기 발광층으로 BH01:BD01 3%로 도핑하여 250 Å 제막하였다. 다음으로 전자수송층으로 ET01:Liq(1:1) 300 Å 제막한 후 LiF 10 Å, 알루미늄(Al) 1000 Å 제막하고, 이 소자를 글로브 박스에서 밀봉(Encapsulation)함으로써 유기 발광 소자를 제작하였다.A glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 Å was washed with distilled water and ultrasonic waves. After cleaning with distilled water, ultrasonic cleaning is performed with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried, and transferred to a plasma cleaner. After cleaning the substrate for 5 minutes using oxygen plasma, a thermal vacuum evaporator (thermal) evaporator) was used to form a hole injection layer HI01 600 Å, HATCN 50 Å, HT01 250 Å as a hole transport layer, and 100 Å of the compound prepared in Preparation Example 1 as a light emitting auxiliary layer, and then doped with BH01:BD01 3% as the light emitting layer. 250 Å was formed. Next, ET01:Liq(1:1) 300 Å was formed as an electron transport layer, LiF 10 Å, and aluminum (Al) 1000 Å were formed into a film, and the organic light emitting device was manufactured by encapsulating the device in a glove box.
<< 실시예Example 2> 내지 < 2> to < 실시예Example 9> 9>
상기 실시예 1과 같은 방법으로 제조하되, 제조예 1에서 제조된 화합물 대신에 각각 제조예 2 내지 제조예 9에서 제조된 화합물을 사용하여 발광보조층으로 제막한 유기 발광 소자를 제작하였다.An organic light emitting device was prepared in the same manner as in Example 1, except that the compound prepared in Preparation Examples 2 to 9 was used instead of the compound prepared in Preparation Example 1 to form an organic light emitting device as a light emitting auxiliary layer.
<< 비교예comparative example 1> 내지 < 1> to < 비교예comparative example 6> 6>
상기 실시예 1과 같은 방법으로 제조하되, 제조예 1 에서 제조된 화합물 대신에 각각 하기 표 3에 표시된 Ref.1 내지 Ref.6을 사용하여 발광보조층으로 제막한 유기발광소자를 제작하였다.An organic light emitting diode film formed as a light emitting auxiliary layer was manufactured in the same manner as in Example 1, except that Ref.1 to Ref.6 shown in Table 3 below were used instead of the compound prepared in Preparation Example 1, respectively.
<유기 발광 소자의 성능평가><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 및 비교예의 유기 발광 소자의 성능을 인가전압에 대한 전류 밀도 및 휘도를 대기압 조건하에 측정하여 평가하였으며, 그 결과를 표 4에 나타내었다.Electrons and holes are injected by applying voltage with a Kiethley 2400 source measurement unit, and the luminance when light is emitted is measured using a Konica Minolta spectroradiometer (CS-2000). By doing so, the performance of the organic light emitting devices of Examples and Comparative Examples was evaluated by measuring current density and luminance with respect to applied voltage under atmospheric pressure conditions, and the results are shown in Table 4.
본 발명의 실시예를 비교예들과 대조해보면, 비교예 1 및 비교예 2와 비교하여, 본 발명 화합물은 플루오렌9번 위치 오쏘 확장된 연결기를 통하여 아릴아민의 질소에 결합된 구조를 가져, 깊은 HOMO와 동시에 높은 LUMO 및 T1을 가질 수 있다.When comparing the examples of the present invention with the comparative examples, compared with Comparative Examples 1 and 2, the compound of the present invention has a structure bonded to the nitrogen of the arylamine through an ortho-extended linking group at the 9th position of fluorene, It can have high LUMO and T1 at the same time as deep HOMO.
또한, 비교예 3 및 비교예 4와 비교하여, 본 발명 화합물은 아민 인접부에 오쏘 위치 확장된 연결기를 가져, 더욱이 깊은 HOMO 및 파이컨쥬게이션 증가를 통한 분자의 박막배열을 우수하게 할 수 있다.In addition, compared to Comparative Examples 3 and 4, the compound of the present invention has an ortho-extended linking group in the vicinity of the amine, and furthermore, it is possible to improve the thin film arrangement of molecules through deep HOMO and increased py-conjugation.
그리고, 비교예5와 비교하여, 본 발명 화합물은 전자주개 역할의 플루오렌을 가져 빠른 홀 모빌리티 및 발광보조층에 용이한 HOMO를 유지할 수 있어 홀 모빌리티 개선에 효과적이고 동시에 전자차단 및 엑시톤 차단이 용이하여 발광층내 전하밸런스가 우수하고 롤오프 현상이 억제될 수 있다.And, compared with Comparative Example 5, the compound of the present invention has fluorene serving as an electron donor, so it can maintain fast hole mobility and easy HOMO in the light emission auxiliary layer, so it is effective in improving hole mobility and at the same time electron blocking and exciton blocking are easy Thus, the charge balance in the light emitting layer is excellent and the roll-off phenomenon can be suppressed.
결론적으로, 실시예들은 비교예들에 비해 낮은 구동전압, 고효율 및 장수명 유기 발광 소자를 구현할 수 있다.As a result, the embodiments may realize a lower driving voltage, high efficiency, and longer lifespan organic light emitting diodes compared to the comparative examples.
100: 기판
200: 정공주입층
300: 정공수송층
400: 발광층
500: 전자수송층
600: 전자주입층
1000: 제1 전극(애노드)
2000: 제2 전극(캐소드)100: 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)
Claims (11)
<화학식 1>
(상기 화학식 1에서,
Ar1은 치환 또는 비치환된 C6~C50의 아릴렌기, 또는 치환 또는 비치환된 C5~C50의 헤테로아릴렌기이고,
Ar2는 치환 또는 비치환된 C6~C50의 아릴기, 또는 치환 또는 비치환된 C5~C50의 헤테로아릴기이고,
L1은 직접결합, 치환 또는 비치환된 C6~C50의 아릴렌기, 또는 치환 또는 비치환된 C2~C50의 헤테로아릴렌기이고,
R, R` 및 R``는 각각 독립적으로 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 C3~C30의 실릴기, 치환 또는 비치환된 C6~C50의 아릴기, 또는 치환 또는 비치환된 C2~C50의 헤테로아릴기이며, R` 및 R``는 서로 결합하여 환을 형성하거나 형성하지 않을 수 있으며,
R1 내지 R5는 각각 독립적으로 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 C3~C30의 실릴기, 치환 또는 비치환된 C6~C50의 아릴기, 또는 치환 또는 비치환된 C2~C50의 헤테로아릴기이며, 인접한 R1끼리, R2끼리, R3끼리, R4끼리, R5끼리 각각 결합하여 환을 형성하거나 형성하지 않을 수 있으며,
l, n, o 및 p는 각각 독립적으로 0 내지 4의 정수이며,
m은 0 내지 3의 정수이다)
A compound represented by the following formula (1).
<Formula 1>
(In Formula 1,
Ar1 is a substituted or unsubstituted C6~ C50 arylene group, or a substituted or unsubstituted C5~ C50 heteroarylene group,
Ar2 is a substituted or unsubstituted C6~ C50 aryl group, or a substituted or unsubstituted C5~ C50 heteroaryl group,
L1 is a direct bond, a substituted or unsubstituted C6~ C50 arylene group, or a substituted or unsubstituted C2~ C50 heteroarylene group,
R, R` and R`` are each independently hydrogen, deuterium, halogen, nitro group, nitrile group, substituted or unsubstituted C1~ C30 alkyl group, substituted or unsubstituted C2~ C30 alkenyl group, substituted or unsubstituted A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 sulfide group, a substituted or unsubstituted C3 to C30 silyl group, a substituted or unsubstituted C6 to C50 aryl group, or a substituted or unsubstituted is a C2~ C50 heteroaryl group, and R` and R`` may or may not form a ring by combining with each other,
R1 to R5 are each independently 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-C30 of an alkoxy group, a substituted or unsubstituted C1~ C30 sulfide group, a substituted or unsubstituted C3~ C30 silyl group, a substituted or unsubstituted C6~ C50 aryl group, or a substituted or unsubstituted C2~ C50 group It is a heteroaryl group, and adjacent R 1 , R 2 , R 3 , R 4 , and R 5 may be bonded to each other to form a ring or not,
l, n, o and p are each independently an integer of 0 to 4,
m is an integer from 0 to 3)
상기 화학식 1은 하기 화학식 2로 표현되는 화합물.
<화학식 2>
(상기 화학식 2에서,
Ar2, R, R`, R``, R1 내지 R5, l, n, o, p, 및 m은 상기 화학식 1에서의 정의와 동일하며,
R6는 상기 R1의 정의와 동일하며,
q는 1 내지 4의 정수이며,
u는 0 내지 4의 정수이다)
According to claim 1,
Formula 1 is a compound represented by Formula 2 below.
<Formula 2>
(In Formula 2,
Ar2, R, R`, R``, R1 to R5, l, n, o, p, and m are the same as defined in Formula 1 above,
R6 is the same as the definition of R1 above,
q is an integer from 1 to 4,
u is an integer from 0 to 4)
상기 화학식 1은 하기 화학식 3으로 표현되는 화합물.
<화학식 3>
(상기 화학식 3에서,
Ar2, R`, R``, R1 내지 R5, l, n, o, p, 및 m은 상기 화학식 1에서의 정의와 동일하며,
Ar은 상기 Ar2의 정의와 동일하다)
According to claim 1,
Formula 1 is a compound represented by Formula 3 below.
<Formula 3>
(In Formula 3,
Ar2, R`, R``, R1 to R5, l, n, o, p, and m are the same as defined in Formula 1 above,
Ar has the same definition as Ar2 above)
상기 화학식 1은 하기 화학식 4로 표현되는 화합물.
<화학식 4>
(상기 화학식 4에서,
Ar2, R`, R``, R1 내지 R5, l, n, o, p, 및 m은 상기 화학식 1에서의 정의와 동일하며,
R7은 상기 R1의 정의와 동일하며,
v는 0 내지 5의 정수이다)
According to claim 1,
Formula 1 is a compound represented by Formula 4 below.
<Formula 4>
(In Formula 4,
Ar2, R`, R``, R1 to R5, l, n, o, p, and m are the same as defined in Formula 1 above,
R7 is the same as the definition of R1 above,
v is an integer from 0 to 5)
상기 R, R`, R``, R1 내지 R5는 각각 독립적으로 수소, 중수소, 메틸기, 또는 페닐기인 화합물.
According to claim 1,
Wherein R, R`, R``, R1 to R5 are each independently hydrogen, deuterium, a methyl group, or a phenyl group.
상기 R` 및 R``은 메틸기인 화합물.
According to claim 1,
Wherein R` and R`` are a methyl group.
상기 Ar2는 페닐, 나프틸, 비페닐, 터페닐, 페난트렌일, 트리페닐렌일, 디메틸플루오렌, 디페닐플루오렌, 스파이로비플루오렌, 디벤조퓨란, 디벤조티오펜, 카바졸 및 이들의 조합으로 이루어진 군에서 선택되는 화합물.
According to claim 1,
Ar2 is phenyl, naphthyl, biphenyl, terphenyl, phenanthrenyl, triphenylenyl, dimethylfluorene, diphenylfluorene, spirobifluorene, dibenzofuran, dibenzothiophene, carbazole, and their A compound selected from the group consisting of combinations.
상기 화학식 1의 화합물이 하기 화학식으로 표현되는 화합물 중 어느 하나인 화합물.
According to claim 1,
The compound of Formula 1 is any one of the compounds represented by the following formula.
An organic light emitting device comprising the compound of any one of claims 1 to 8.
상기 화합물은 정공주입층, 정공수송층 및 발광보조층 중 어느 하나 이상의 유기물층에 포함되는 유기 발광 소자.
10. The method of claim 9,
The compound is an organic light emitting device included in at least one organic material layer of a hole injection layer, a hole transport layer, and a light emitting auxiliary layer.
상기 화합물은 정공수송층과 발광층 사이에 위치하는 발광보조층에 포함되는 유기 발광 소자.10. The method of claim 9,
The compound is an organic light emitting device included in the light emitting auxiliary layer positioned between the hole transport layer and the light emitting layer.
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