KR20230056444A - Novel compound and organic light emitting device comprising the same - Google Patents
Novel compound and organic light emitting device comprising the same Download PDFInfo
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- KR20230056444A KR20230056444A KR1020210140469A KR20210140469A KR20230056444A KR 20230056444 A KR20230056444 A KR 20230056444A KR 1020210140469 A KR1020210140469 A KR 1020210140469A KR 20210140469 A KR20210140469 A KR 20210140469A KR 20230056444 A KR20230056444 A KR 20230056444A
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- South Korea
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- light emitting
- compound
- emitting device
- organic light
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- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
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Abstract
Description
본 발명은 신규한 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다.The present invention relates to a novel compound and an organic light emitting device including the same.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 넓은 시야각, 우수한 콘트라스트, 빠른 응답 시간을 가지며, 휘도, 구동 전압 및 응답 속도 특성이 우수하여 많은 연구가 진행되고 있다. In general, the organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, and a fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.
유기 발광 소자는 일반적으로 양극과 음극 및 상기 양극과 음극 사이에 유기물층을 포함하는 구조를 가진다. 상기 유기물층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. An organic light emitting device generally has a structure including an anode, a cathode, and an organic material layer between the anode and the cathode. In order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often composed of a multi-layered structure composed of different materials, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. In the structure of this organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and when the injected holes and electrons meet, excitons are formed. When it falls back to the ground state, it glows.
상기와 같은 유기 발광 소자에 사용되는 유기물에 대하여 새로운 재료의 개발이 지속적으로 요구되고 있다.The development of new materials for organic materials used in the organic light emitting device as described above is continuously required.
한편, 최근에는 공정 비용 절감을 위하여 기존의 증착 공정 대신 용액 공정, 특히 잉크젯 공정을 이용한 유기 발광 소자가 개발되고 있다. 초창기에는 모든 유기 발광 소자 층을 용액 공정으로 코팅하여 유기 발광 소자를 개발하려 하였으나 현재 기술로는 한계가 있어, 정구조 형태에서 HIL, HTL, EML만을 용액 공정으로 진행하고 추후 공정은 기존의 증착 공정을 활용하는 하이브리드(hybrid) 공정이 연구 중이다. Meanwhile, in recent years, an organic light emitting device using a solution process, particularly an inkjet process, instead of a conventional deposition process has been developed to reduce process costs. In the early days, an attempt was made to develop an organic light emitting device by coating all organic light emitting device layers with a solution process, but the current technology has limitations, so only HIL, HTL, and EML in the form of a regular structure are carried out as a solution process, and the subsequent process is the existing deposition process A hybrid process that utilizes is being studied.
이에 본 발명에서는 유기 발광 소자에 사용될 수 있으면서 동시에 용액 공정에 사용 가능한 신규한 유기 발광 소자의 소재를 제공한다.Accordingly, the present invention provides a novel organic light emitting device material that can be used in an organic light emitting device and can be used in a solution process at the same time.
본 발명은 신규한 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다.The present invention relates to a novel compound and an organic light emitting device including the same.
본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다: The present invention provides a compound represented by Formula 1 below:
[화학식 1][Formula 1]
상기 화학식 1에서, In Formula 1,
X는 O, 또는 S이고, X is O or S;
Ar1은 치환 또는 비치환된 C6-60 아릴렌이고,Ar 1 is a substituted or unsubstituted C 6-60 arylene;
L은 치환 또는 비치환된 C1-10 알킬렌이고,L is a substituted or unsubstituted C 1-10 alkylene;
Ar2는 치환 또는 비치환된 C6-60 아릴이고, Ar 2 is a substituted or unsubstituted C 6-60 aryl;
Ar3은 치환 또는 비치환된 C6-60 아릴이다. Ar 3 is a substituted or unsubstituted C 6-60 aryl.
또한, 본 발명은 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물 층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화학식 1로 표시되는 화합물을 포함하는, 유기 발광 소자를 제공한다.In addition, the present invention is a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Chemical Formula 1. do.
상술한 화학식 1로 표시되는 화합물은 유기 발광 소자의 유기물층의 재료로서 사용될 수 있으며, 또한 용액 공정에 사용이 가능하며, 유기 발광 소자에서 효율의 향상, 낮은 구동전압 및/또는 수명 특성을 향상시킬 수 있다.The compound represented by Formula 1 described above can be used as a material for an organic layer of an organic light emitting device, and can also be used in a solution process, and can improve efficiency, low driving voltage and/or lifespan characteristics in an organic light emitting device. there is.
도 1은 기판(1), 양극(2), 발광층(3), 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.
도 2는 기판 (1), 양극(2), 정공주입층(5), 정공수송층(6), 발광층(7), 전자수송층(8), 전자주입층(9) 및 음극(4)로 이루어진 유기 발광 소자의 예를 도시한 것이다. 1 shows an example of an organic light emitting device composed of a
2 is composed of a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (7), an electron transport layer (8), an electron injection layer (9) and a cathode (4). An example of an organic light emitting device is shown.
이하, 본 발명의 이해를 돕기 위하여 보다 상세히 설명한다.Hereinafter, in order to aid understanding of the present invention, it will be described in more detail.
(용어의 정의)(Definition of Terms)
본 명세서에서, 
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 시아노기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 아미노기; 포스핀옥사이드기; 알콕시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 알킬기; 사이클로알킬기; 알케닐기; 아릴기; 아르알킬기; 아르알케닐기; 알킬아릴기; 알킬아민기; 아랄킬아민기; 헤테로아릴아민기; 아릴아민기; 아릴포스핀기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 헤테로아릴로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환되거나, 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환 또는 비치환된 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 비페닐기일 수 있다. 즉, 비페닐이기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수도 있다.In this specification, the term "substituted or unsubstituted" means deuterium; halogen group; cyano group; nitro group; hydroxy group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy group; Alkyl thioxy group; Arylthioxy group; an alkyl sulfoxy group; aryl sulfoxy group; silyl group; boron group; an alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; Aralkenyl group; Alkyl aryl group; Alkylamine group; Aralkylamine group; heteroarylamine group; Arylamine group; Arylphosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heteroaryl containing at least one of N, O, and S atoms, or substituted or unsubstituted with two or more substituents linked to each other among the substituents exemplified above. . For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.
본 명세서에서 카보닐기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 40인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
본 명세서에 있어서, 에스테르기는 에스테르기의 산소가 탄소수 1 내지 25의 직쇄, 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 25의 아릴기로 치환될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the ester group may be substituted with an aryl group having 6 to 25 carbon atoms or a straight-chain, branched-chain or cyclic chain alkyl group having 1 to 25 carbon atoms in the ester group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
본 명세서에 있어서, 이미드기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 25인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
본 명세서에 있어서, 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다. In the present specification, the silyl group is specifically a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. but not limited to
본 명세서에 있어서, 붕소기는 구체적으로 트리메틸붕소기, 트리에틸붕소기, t-부틸디메틸붕소기, 트리페닐붕소기, 페닐붕소기 등이 있으나 이에 한정되지 않는다.In the present specification, the boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, but is not limited thereto.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.In this specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 6이다. 알킬기의 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸, 1-메틸-부틸, 1-에틸-부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 헥실, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸-2-펜틸, 3,3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸, 1-메틸헥실, 사이클로펜틸메틸, 사이클로헥틸메틸, 옥틸, n-옥틸, tert-옥틸, 1-메틸헵틸, 2-에틸헥실, 2-프로필펜틸, n-노닐, 2,2-디메틸헵틸, 1-에틸-프로필, 1,1-디메틸-프로필, 이소헥실, 2-메틸펜틸, 4-메틸헥실, 5-메틸헥실 등이 있으나, 이들에 한정되지 않는다.In the present specification, the alkyl group may be straight-chain or branched-chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 10. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but is not limited thereto.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 6이다. 구체적인 예로는 비닐, 1-프로페닐, 이소프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 1-펜테닐, 2-펜테닐, 3-펜테닐, 3-메틸-1-부테닐, 1,3-부타디에닐, 알릴, 1-페닐비닐-1-일, 2-페닐비닐-1-일, 2,2-디페닐비닐-1-일, 2-페닐-2-(나프틸-1-일)비닐-1-일, 2,2-비스(디페닐-1-일)비닐-1-일, 스틸베닐기, 스티레닐기 등이 있으나 이들에 한정되지 않는다.In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, etc., but is not limited thereto.
본 명세서에 있어서, 사이클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 일 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 사이클로프로필, 사이클로부틸, 사이클로펜틸, 3-메틸사이클로펜틸, 2,3-디메틸사이클로펜틸, 사이클로헥실, 3-메틸사이클로헥실, 4-메틸사이클로헥실, 2,3-디메틸사이클로헥실, 3,4,5-트리메틸사이클로헥실, 4-tert-부틸사이클로헥실, 사이클로헵틸, 사이클로옥틸 등이 있으나, 이에 한정되지 않는다.In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며, 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는 페닐기, 비페닐이기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난쓰레닐기, 파이레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc. as a monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.
본 명세서에 있어서, 플루오레닐기는 치환될 수 있고, 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다. 상기 플루오레닐기가 치환되는 경우, 
본 명세서에 있어서, 헤테로아릴은 이종 원소로 O, N, Si 및 S 중 1개 이상을 포함하는 헤테로아릴로서, 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 60인 것이 바람직하다. 헤테로아릴의 예로는 잔텐(xanthene), 티오잔텐(thioxanthen), 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기, 아크리딜기, 피리다진기, 피라지닐기, 퀴놀리닐기, 퀴나졸린기, 퀴녹살리닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤즈옥사졸기, 벤조이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 페난쓰롤린기(phenanthroline), 이소옥사졸릴기, 티아디아졸릴기, 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, heteroaryl is a heteroaryl containing at least one of O, N, Si, and S as a heterogeneous element, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms. Examples of the heteroaryl include xanthene, thioxanthen, thiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, triazole, pyridyl, bipyridyl, Pyrimidyl group, triazine group, acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazino Pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group ( phenanthroline), an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto.
본 명세서에 있어서, 아르알킬기, 아르알케닐기, 알킬아릴기, 아릴아민기, 아릴실릴기 중의 아릴기는 전술한 아릴기의 예시와 같다. 본 명세서에 있어서, 아르알킬기, 알킬아릴기, 알킬아민기 중 알킬기는 전술한 알킬기의 예시와 같다. 본 명세서에 있어서, 헤테로아릴아민 중 헤테로아릴은 전술한 헤테로아릴에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 아르알케닐기 중 알케닐기는 전술한 알케닐기의 예시와 같다. 본 명세서에 있어서, 아릴렌은 2가기인 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 헤테로아릴렌은 2가기인 것을 제외하고는 전술한 헤테로아릴에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 탄화수소 고리는 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 아릴기 또는 사이클로알킬기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 헤테로고리는 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 헤테로아릴에 관한 설명이 적용될 수 있다.In the present specification, an aralkyl group, an aralkenyl group, an alkylaryl group, an arylamine group, and an aryl group among arylsilyl groups are the same as the examples of the aryl group described above. In the present specification, the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the examples of the above-mentioned alkyl group. In the present specification, the description of the above-described heteroaryl may be applied to the heteroaryl among heteroarylamines. In the present specification, the alkenyl group among the aralkenyl groups is the same as the examples of the alkenyl group described above. In the present specification, the description of the aryl group described above may be applied except that the arylene is a divalent group. In the present specification, the description of heteroaryl described above may be applied except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the aryl group or cycloalkyl group described above may be applied, except that the hydrocarbon ring is formed by combining two substituents. In the present specification, the heterocyclic group is not a monovalent group, and the description of the above-described heteroaryl may be applied, except that it is formed by combining two substituents.
(화합물)(compound)
본 발명은 상기 화학식 1로 표시되는 화합물을 제공한다. The present invention provides a compound represented by
바람직하게는, Ar1은 비치환되거나, 또는 중수소, C1-60 알킬, 할로겐, -O-Li, 또는 -S-Li로 치환된 C6-20 아릴이다. Preferably, Ar 1 is C 6-20 aryl that is unsubstituted or substituted with deuterium, C 1-60 alkyl, halogen, -O-Li, or -S-Li.
바람직하게는, Ar1은 페닐렌이고, 상기 페닐렌은 비치환되거나, 또는 중수소, 메틸, 에틸, 프로필, 이소프로필, 부틸, 이소부틸, 터트부틸, 플루오로, 클로로, -O-Li, 또는 -S-Li로 치환된다. Preferably, Ar 1 is phenylene, which phenylene is unsubstituted, or deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertbutyl, fluoro, chloro, -O-Li, or It is substituted with -S-Li.
바람직하게는, L은 치환 또는 비치환된 C1-4 알킬렌이다. Preferably, L is a substituted or unsubstituted C 1-4 alkylene.
바람직하게는, L은 -CH2-, -CH2CH2-, -CH2CH2CH2-, 또는 -CH2CH2CH2CH2-이다. Preferably, L is -CH 2 -, -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -, or -CH 2 CH 2 CH 2 CH 2 -.
바람직하게는, Ar2 및 Ar3은 각각 독립적으로 비치환되거나, 또는 중수소, C1-60 알킬, 또는 할로겐으로 치환된 C6-20 아릴이다. Preferably, Ar 2 and Ar 3 are each independently unsubstituted or C 6-20 aryl substituted with deuterium, C 1-60 alkyl, or halogen.
바람직하게는, Ar2 및 Ar3은 페닐이고, 상기 페닐은 비치환되거나, 또는 중수소, 메틸, 에틸, 프로필, 이소프로필, 부틸, 이소부틸, 터트부틸, 플루오로, 또는 클로로로 치환된다. Preferably, Ar 2 and Ar 3 are phenyl, which phenyl is unsubstituted or substituted with deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertbutyl, fluoro, or chloro.
바람직하게는, Ar2 및 Ar3은 서로 동일하다. Preferably, Ar 2 and Ar 3 are identical to each other.
바람직하게는, 상기 화학식 1은 하기 화학식 1-1로 표시된다:Preferably,
[화학식 1-1][Formula 1-1]
상기 화학식 1-1에서,In Formula 1-1,
X는 O, 또는 S이고, X is O or S;
R1은 수소, 중수소, C1-60 알킬, 할로겐, -O-Li, 또는 -S-Li이고,R 1 is hydrogen, deuterium, C 1-60 alkyl, halogen, -O-Li, or -S-Li;
R2 및 R3은 각각 독립적으로, 수소, 중수소, C1-60 알킬, 또는 할로겐이고, R 2 and R 3 are each independently hydrogen, deuterium, C 1-60 alkyl, or halogen;
n은 1 내지 10의 정수이다. n is an integer from 1 to 10;
바람직하게는, R1은 수소, 중수소, 메틸, 에틸, 프로필, 이소프로필, 부틸, 이소부틸, 터트부틸, 플루오로, 클로로, -O-Li, 또는 -S-Li이다. Preferably, R 1 is hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertbutyl, fluoro, chloro, -O-Li, or -S-Li.
바람직하게는, R2 및 R3은 각각 독립적으로, 수소, 중수소, 메틸, 에틸, 프로필, 이소프로필, 부틸, 이소부틸, 터트부틸, 플루오로, 또는 클로로이다. Preferably, R 2 and R 3 are each independently hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertbutyl, fluoro, or chloro.
바람직하게는, n은 1 내지 4의 정수이고, 보다 바람직하게는 n은 1이다. Preferably, n is an integer from 1 to 4, more preferably n is 1.
상기 화학식 1로 표시되는 화합물의 대표적인 예는 하기와 같다:Representative examples of the compound represented by
한편, 본 발명은 일례로 하기 반응식 1과 같은 상기 화학식 1로 표시되는 화합물의 제조방법을 제공한다:On the other hand, the present invention provides a method for producing a compound represented by
[반응식 1][Scheme 1]
상기 반응은 출발물질과 오가노리튬 화합물(organolithium agent)을 반응시키는 반응이다. 상기 반응에 사용될 수 있는 오가노리튬 화합물은 제조하고자 하는 화합물에 따라 적절히 선택할 수 있다. 상기 제조 방법은 후술할 제조예에서 보다 구체화될 수 있다.The above reaction is a reaction in which a starting material and an organolithium agent are reacted. The organolithium compound that can be used in the above reaction can be appropriately selected depending on the compound to be produced. The manufacturing method may be more specific in Preparation Examples to be described later.
한편, 본 발명에 따른 화합물을 포함하는 유기물층은 진공 증착법, 용액 공정 등과 같은 다양한 방법을 이용하여 형성할 수 있으며, 용액 공정에 대해서는 이하 상세히 설명한다. Meanwhile, the organic layer containing the compound according to the present invention can be formed using various methods such as a vacuum deposition method and a solution process, and the solution process will be described in detail below.
(코팅 조성물)(coating composition)
한편, 본 발명에 따른 화합물은 용액 공정으로 유기 발광 소자의 유기물 층, 특히 전자수송층 또는 전자주입층을 형성할 수 있다. 이를 위하여, 본 발명은 상술한 본 발명에 따른 화합물 및 용매를 포함하는 코팅 조성물을 제공한다. Meanwhile, the compound according to the present invention may form an organic material layer of an organic light emitting device, particularly an electron transport layer or an electron injection layer, through a solution process. To this end, the present invention provides a coating composition comprising the above-described compound and a solvent according to the present invention.
상기 용매는 본 발명에 따른 화합물을 용해 또는 분산시킬 수 있는 용매이면 특별히 제한되지 않으며, 일례로 클로로포름, 염화메틸렌, 1,2-디클로로에탄, 1,1,2-트리클로로에탄, 클로로벤젠, o-디클로로벤젠 등의 염소계 용매; 테트라하이드로퓨란, 디옥산 등의 에테르계 용매; 톨루엔, 크실렌, 트리메틸벤젠, 메시틸렌 등의 방향족 탄화수소계 용매; 시클로헥산, 메틸시클로헥산, n-펜탄, n-헥산, n-헵탄, n-옥탄, n-노난, n-데칸 등의 지방족 탄화수소계 용매; 아세톤, 메틸에틸케톤, 시클로헥사논 등의 케톤계 용매; 아세트산에틸, 아세트산부틸, 에틸셀로솔브아세테이트 등의 에스테르계 용매; 에틸렌글리콜, 에틸렌글리콜모노부틸에테르, 에틸렌글리콜모노에틸에테르, 에틸렌글리콜모노메틸에테르, 디메톡시에탄, 프로필렌글리콜, 디에톡시메탄, 트리에틸렌글리콜모노에틸에테르, 글리세린, 1,2-헥산디올 등의 다가 알코올 및 그의 유도체; 메탄올, 에탄올, 프로판올, 이소프로판올, 시클로헥산올 등의 알코올계 용매; 디메틸술폭사이드 등의 술폭사이드계 용매; 및 N-메틸-2-피롤리돈, N,N-디메틸포름아미드 등의 아미드계 용매; 부틸벤조에이트, 메틸-2-메톡시벤조에이트 등의 벤조에이트계 용매; 테트랄린; 3-페녹시톨루엔 등의 용매를 들 수 있다. 또한, 상술한 용매를 1종 단독으로 사용하거나 2종 이상의 용매를 혼합하여 사용할 수 있다. 바람직하게는 상기 용매로 톨루엔을 사용할 수 있다. The solvent is not particularly limited as long as it can dissolve or disperse the compound according to the present invention, and examples thereof include chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o -Chlorinated solvents such as dichlorobenzene; ether solvents such as tetrahydrofuran and dioxane; aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, and mesitylene; aliphatic hydrocarbon-based solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; Ketone solvents, such as acetone, methyl ethyl ketone, and cyclohexanone; Ester solvents, such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; Ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol, etc. alcohol and its derivatives; alcohol solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; and amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; benzoate solvents such as butyl benzoate and methyl-2-methoxy benzoate; tetralin; Solvents, such as 3-phenoxytoluene, are mentioned. In addition, the above-mentioned solvent may be used alone or in combination of two or more solvents. Preferably, toluene may be used as the solvent.
또한, 상기 코팅 조성물의 점도는 1 cP 이상이 바람직하다. 또한, 상기 코팅 조성물의 코팅 용이성을 감안하여, 상기 코팅 조성물의 점도는 10 cP 이하가 바람직하다. 또한, 상기 코팅 조성물 내 본 발명에 따른 화합물의 농도는 0.1 wt/v% 이상이 바람직하다. 또한, 상기 코팅 조성물이 최적으로 코팅될 수 있도록, 상기 코팅 조성물 내 본 발명에 따른 화합물의 농도는 20 wt/v%이하가 바람직하다. In addition, the viscosity of the coating composition is preferably 1 cP or more. In addition, considering the ease of coating of the coating composition, the viscosity of the coating composition is preferably 10 cP or less. Also, the concentration of the compound according to the present invention in the coating composition is preferably 0.1 wt/v% or more. In addition, the concentration of the compound according to the present invention in the coating composition is preferably 20 wt / v% or less so that the coating composition can be coated optimally.
또한, 본 발명은 상술한 코팅 조성물을 사용하여 발광층을 형성하는 방법을 제공한다. 구체적으로, 양극 상에, 또는 양극 상에 형성된 정공 수송층 상에 상술한 본 발명에 따른 발광층을 용액 공정으로 코팅하는 단계; 및 상기 코팅된 코팅 조성물을 열처리하는 단계를 포함한다. In addition, the present invention provides a method of forming a light emitting layer using the coating composition described above. Specifically, coating the light emitting layer according to the present invention described above on the anode or on the hole transport layer formed on the anode by a solution process; and heat-treating the coated coating composition.
상기 용액 공정은 상술한 본 발명에 따른 코팅 조성물을 사용하는 것으로, 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.The solution process uses the above-described coating composition according to the present invention, and includes spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.
상기 열처리 단계에서 열처리 온도는 150 내지 230℃가 바람직하다. 또한, 상기 열처리 시간은 1분 내지 3시간이고, 보다 바람직하게는 10분 내지 1시간이다. 또한, 상기 열처리는 아르곤, 질소 등의 불활성 기체 분위기에서 수행하는 것이 바람직하다. In the heat treatment step, the heat treatment temperature is preferably 150 to 230 °C. In addition, the heat treatment time is 1 minute to 3 hours, more preferably 10 minutes to 1 hour. In addition, the heat treatment is preferably performed in an inert gas atmosphere such as argon or nitrogen.
(유기 발광 소자)(organic light emitting element)
또한, 본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기 발광 소자를 제공한다. 일례로, 본 발명은 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물 층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화학식 1로 표시되는 화합물을 포함하는, 유기 발광 소자를 제공한다. In addition, the present invention provides an organic light emitting device including the compound represented by
본 발명의 유기 발광 소자의 유기물 층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 발명의 유기 발광 소자는 유기물 층으로서 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등을 포함하는 구조를 가질 수 있다. 그러나 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기층을 포함할 수 있다.The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as organic layers. However, the structure of the organic light emitting device is not limited thereto and may include fewer organic layers.
또한, 상기 유기물 층은 전자수송층 또는 전자주입층을 포함할 수 있고, 상기 전자수송층 또는 전자주입층은 상기 화학식 1로 표시되는 화합물을 포함한다. In addition, the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or electron injection layer includes the compound represented by
또한, 본 발명에 따른 유기 발광 소자는, 기판 상에 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층된 구조(normal type)의 유기 발광 소자일 수 있다. 또한, 본 발명에 따른 유기 발광 소자는 기판 상에 음극, 1층 이상의 유기물층 및 양극이 순차적으로 적층된 역방향 구조(inverted type)의 유기 발광 소자일 수 있다. 예컨대, 본 발명의 일실시예에 따른 유기 발광 소자의 구조는 도 1 및 2에 예시되어 있다.Also, the organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light emitting device according to the present invention may be an organic light emitting device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2 .
도 1은 기판(1), 양극(2), 발광층(3), 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 발광층에 포함될 수 있다. 1 shows an example of an organic light emitting device composed of a
도 2는 기판 (1), 양극(2), 정공주입층(5), 정공수송층(6), 발광층(7), 전자수송층(8), 전자주입층(9) 및 음극(4)로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 전자수송층 또는 전자주입층에 포함될 수 있다.2 is composed of a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (7), an electron transport layer (8), an electron injection layer (9) and a cathode (4). An example of an organic light emitting device is shown. In this structure, the compound represented by
본 발명에 따른 유기 발광 소자는, 상기 유기물 층 중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다. 또한, 상기 유기 발광 소자가 복수개의 유기물층을 포함하는 경우, 상기 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다. The organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that at least one of the organic layers includes the compound represented by
예컨대, 본 발명에 따른 유기 발광 소자는 기판 상에 양극, 유기물층 및 음극을 순차적으로 적층시켜 제조할 수 있다. 이때, 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 PVD(physical Vapor Deposition) 방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공 주입층, 정공 수송층, 발광층 및 전자 수송층을 포함하는 유기물 층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시켜 제조할 수 있다. For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate. At this time, using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, depositing a metal or a metal oxide having conductivity or an alloy thereof on the substrate to form an anode After forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and depositing a material that can be used as a cathode thereon, it can be prepared.
이와 같은 방법 외에도, 기판 상에 음극 물질로부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 제조할 수 있다(WO 2003/012890). 다만, 제조 방법이 이에 한정되는 것은 아니다. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate from a cathode material (WO 2003/012890). However, the manufacturing method is not limited thereto.
일례로, 상기 제1 전극은 양극이고, 상기 제2 전극은 음극이거나, 또는 상기 제1 전극은 음극이고, 상기 제2 전극은 양극이다.In one example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.
상기 양극 물질로는 통상 유기물층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 상기 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO), 인듐아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 화합물 등이 있으나, 이들에만 한정되는 것은 아니다. As the anode material, a material having a high work function is generally preferred so that holes can be smoothly injected into the organic material layer. Specific examples of the cathode material include metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; conductive compounds such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; and the like, but are not limited thereto.
상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 상기 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다. The cathode material is preferably a material having a small work function so as to easily inject electrons into the organic material layer. Specific examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multi-layered materials such as LiF/Al or LiO 2 /Al, but are not limited thereto.
본 발명에 따른 유기 발광 소자는, 상기 전자억제층과 양극 사이에 정공수송층을 포함할 수 있다. The organic light emitting device according to the present invention may include a hole transport layer between the electron blocking layer and the anode.
상기 정공수송층은 정공주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로, 정공 수송 물질로 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. As a hole transport material, a material capable of receiving holes from the anode or the hole injection layer and transferring them to the light emitting layer is a material having high hole mobility. this is suitable
상기 정공 수송 물질의 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다. Specific examples of the hole transport material include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated parts.
본 발명에 따른 유기 발광 소자는, 필요에 따라 상기 양극과 정공수송층 사이에 정공주입층을 추가로 포함할 수 있다. The organic light emitting device according to the present invention may further include a hole injection layer between the anode and the hole transport layer, if necessary.
상기 정공주입층은 전극으로부터 정공을 주입하는 층으로, 정공 주입 물질로는 정공을 수송하는 능력을 가져 양극에서의 정공 주입효과, 발광층 또는 발광재료에 대하여 우수한 정공 주입 효과를 갖고, 발광층에서 생성된 여기자의 전자주입층 또는 전자주입재료에의 이동을 방지하며, 또한, 박막 형성 능력이 우수한 화합물이 바람직하다. 또한, 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물 층의 HOMO 사이인 것이 바람직하다. The hole injection layer is a layer for injecting holes from the electrode, and the hole injection material has the ability to transport holes and has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and generated in the light emitting layer A compound that prevents migration of excitons to the electron injecting layer or electron injecting material and has excellent thin film formation ability is preferred. In addition, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer.
정공 주입 물질의 구체적인 예로는 금속 포피린(porphyrin), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴헥사아자트리페닐렌 계열의 유기물, 퀴나크리돈(quinacridone)계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정 되는 것은 아니다. Specific examples of the hole injection material include metal porphyrins, oligothiophenes, arylamine-based organic materials, hexanitrilehexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene-based organic materials. of organic matter, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
본 발명에 따른 유기 발광 소자는, 상기 발광층과 음극 사이에 전자수송층을 포함할 수 있다. The organic light emitting device according to the present invention may include an electron transport layer between the light emitting layer and the cathode.
상기 전자수송층은, 음극 또는 음극 상에 형성된 전자주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하고, 또한 발광층에서 정공이 전달되는 것을 억제하는 층으로, 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다.The electron transport layer is a layer that receives electrons from the cathode or an electron injection layer formed on the cathode, transports electrons to the light emitting layer, and suppresses the transfer of holes in the light emitting layer. As an electron transport material, electrons are well injected from the cathode. As a material that can be received and transferred to the light emitting layer, a material having high electron mobility is suitable.
상기 전자 수송 물질의 구체적인 예로는 8-히드록시퀴놀린의 Al 착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다. 전자 수송층은 종래기술에 따라 사용된 바와 같이 임의의 원하는 캐소드 물질과 함께 사용할 수 있다. 특히, 적절한 캐소드 물질의 예는 낮은 일함수를 가지고 알루미늄층 또는 실버층이 뒤따르는 통상적인 물질이다. 구체적으로 세슘, 바륨, 칼슘, 이테르븀 및 사마륨이고, 각 경우 알루미늄 층 또는 실버층이 뒤따른다.Specific examples of the electron transport material include Al complexes of 8-hydroxyquinoline; Complexes containing Alq 3 ; organic radical compounds; Hydroxyflavone-metal complexes, etc., but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function followed by a layer of aluminum or silver. Specifically cesium, barium, calcium, ytterbium and samarium, followed in each case by a layer of aluminum or silver.
본 발명에 따른 유기 발광 소자는 필요에 따라 상기 전자수송층과 음극 사이에 전자주입층을 추가로 포함할 수 있다. The organic light emitting device according to the present invention may further include an electron injection layer between the electron transport layer and the cathode, if necessary.
상기 전자주입층은 전극으로부터 전자를 주입하는 층으로, 전자를 수송하는 능력을 갖고, 음극으로부터의 전자 주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며, 발광층에서 생성된 여기자의 정공주입층에의 이동을 방지하고, 또한, 박막형성능력이 우수한 화합물을 사용하는 것이 바람직하다. The electron injection layer is a layer for injecting electrons from an electrode, has the ability to transport electrons, has an excellent electron injection effect from a cathode, an excellent electron injection effect for a light emitting layer or a light emitting material, and injects holes of excitons generated in the light emitting layer. It is preferable to use a compound that prevents migration to a layer and has excellent thin film forming ability.
상기 전자주입층으로 사용될 수 있는 물질의 구체적인 예로는, 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 질소 함유 5원환 유도체 등이 있으나, 이에 한정되지 않는다. Specific examples of materials that can be used as the electron injection layer include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preore nylidene methane, anthrone, etc. and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives, etc., but are not limited thereto.
상기 금속 착체 화합물로서는 8-하이드록시퀴놀리나토 리튬, 비스(8-하이드록시퀴놀리나토)아연, 비스(8-하이드록시퀴놀리나토)구리, 비스(8-하이드록시퀴놀리나토)망간, 트리스(8-하이드록시퀴놀리나토)알루미늄, 트리스(2-메틸-8-하이드록시퀴놀리나토)알루미늄, 트리스(8-하이드록시퀴놀리나토)갈륨, 비스(10-하이드록시벤조[h]퀴놀리나토)베릴륨, 비스(10-하이드록시벤조[h]퀴놀리나토)아연, 비스(2-메틸-8-퀴놀리나토)클로로갈륨, 비스(2-메틸-8-퀴놀리나토)(o-크레졸라토)갈륨, 비스(2-메틸-8-퀴놀리나토)(1-나프톨라토)알루미늄, 비스(2-메틸-8-퀴놀리나토)(2-나프톨라토)갈륨 등이 있으나, 이에 한정되지 않는다.Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato) aluminum, tris(2-methyl-8-hydroxyquinolinato) aluminum, tris(8-hydroxyquinolinato) gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( There are o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtolato)gallium. Not limited to this.
상술한 재료 외에도, 상기 발광층, 정공주입층, 정공수송층, 전자수송층, 및 전자주입층에는 퀀텀닷 등의 무기 화합물 또는 고분자 화합물을 추가로 포함할 수 있다.In addition to the above materials, inorganic compounds or polymer compounds such as quantum dots may be further included in the light emitting layer, the hole injection layer, the hole transport layer, the electron transport layer, and the electron injection layer.
상기 퀀텀닷은 예를 들어, 콜로이드 퀀텀닷, 합금 퀀텀닷, 코어셸 퀀텀닷, 또는 코어 퀀텀닷일 수 있다. 제2족 및 제16족에 속하는 원소, 제13족 및 제15족에 속하는 원소, 제13족 및 제17족에 속하는 원소, 제11족 및 제17족에 속하는 원소, 또는 제14족 및 제15족에 속하는 원소를 포함하는 퀀텀닷일 수 있으며, 카드뮴(Cd), 셀레늄(Se), 아연(Zn), 황(S), 인(P), 인듐(In), 텔루륨(Te), 납(Pb), 갈륨(Ga), 비소(As) 등의 원소를 포함하는 퀀텀닷이 사용될 수 있다.The quantum dot may be, for example, a colloidal quantum dot, an alloy quantum dot, a core-shell quantum dot, or a core quantum dot. An element belonging to
본 발명에 따른 유기 발광 소자는 배면 발광(bottom emission) 소자, 전면 발광(top emission) 소자, 또는 양면 발광 소자일 수 있으며, 특히 상대적으로 높은 발광 효율이 요구되는 배면 발광 소자일 수 있다.The organic light emitting device according to the present invention may be a bottom emission device, a top emission device, or a double-sided light emitting device, and in particular, may be a bottom emission device requiring relatively high light emitting efficiency.
또한, 본 발명에 따른 화합물은 유기 발광 소자 외에도 유기 태양 전지 또는 유기 트랜지스터에 포함될 수 있다.In addition, the compound according to the present invention may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.
상기 화학식 1로 표시되는 화합물 및 이를 포함하는 유기 발광 소자의 제조는 이하 실시예에서 구체적으로 설명한다. 그러나 하기 실시예는 본 발명을 예시하기 위한 것이며, 본 발명의 범위가 이들에 의하여 한정되는 것은 아니다.Preparation of the compound represented by
[실시예][Example]
실시예 1: 화합물 1의 제조Example 1: Preparation of
플라스크에 (2-하이드록시벤질)디페닐포스핀 옥사이드(5 g, 16.2169 mmol), 및 무수 아세토나이트릴(100 mL)을 투입하고 5분 동안 교반하였다. 상기 플라스크에 리튬 하이드라이드(129 mg, 16.2169 mmol)을 투입하고 24시간 동안 교반하였다. 반응이 끝나면 아세토나이트릴을 사용하여 반응 용액을 필터하여 고체를 얻었다. 상기 고체를 승화하여 화합물 1(3.2 g)을 얻었다. (2-hydroxybenzyl) diphenylphosphine oxide (5 g, 16.2169 mmol) and anhydrous acetonitrile (100 mL) were added to the flask and stirred for 5 minutes. Lithium hydride (129 mg, 16.2169 mmol) was added to the flask and stirred for 24 hours. After the reaction was completed, the reaction solution was filtered using acetonitrile to obtain a solid. The solid was sublimated to obtain Compound 1 (3.2 g).
m/z: 308.10m/z: 308.10
실시예 2: 화합물 2의 제조Example 2: Preparation of
(단계 1)(Step 1)
플라스크에 디-p-톨릴포스피닉 클로라이드(184.2450 mmol, 4.5 eq), 소듐 아이오다이드(184.2450 mmol, 4.5 eq), 및 무수 아세토나이트릴(184 mL, 1 M)을 투입하고 교반하였다. 상기 반응액에 2-하이드록시벤즈알데하이드(5.0 g, 40.9433 mmol, 1.0 eq)을 투입하였다. 반응액을 80℃로 승온하고 24시간 동안 교반하였다. 반응액을 상온으로 냉각하고 30% 과산화수소 수용액(20 mL)을 천천히 투입하였다. 10분 후 소듐 티오설페이트 포화 수용액을 투입하였다. 유기층을 디클로로메탄으로 추출하고 마그네슘 설페이트로 건조하였다. 용매를 감압하여 제거하였다. 실리카겔 컬럼으로 정제하여 (2-하이드록시벤질)디-p-톨릴포스핀 옥사이드(8 g)를 얻었다. Di-p-tolylphosphinic chloride (184.2450 mmol, 4.5 eq), sodium iodide (184.2450 mmol, 4.5 eq), and anhydrous acetonitrile (184 mL, 1 M) were added to the flask and stirred. 2-hydroxybenzaldehyde (5.0 g, 40.9433 mmol, 1.0 eq) was added to the reaction solution. The temperature of the reaction solution was raised to 80 °C and stirred for 24 hours. The reaction solution was cooled to room temperature, and 30% hydrogen peroxide aqueous solution (20 mL) was slowly added thereto. After 10 minutes, a saturated aqueous solution of sodium thiosulfate was added. The organic layer was extracted with dichloromethane and dried over magnesium sulfate. The solvent was removed under reduced pressure. Purification by silica gel column gave (2-hydroxybenzyl)di-p-tolylphosphine oxide (8 g).
(단계 2)(Step 2)
플라스크에 앞서 단계 1에서 제조한 (2-하이드록시벤질)디-p-톨릴포스핀 옥사이드(8 g, 23.7833 mmol), 및 무수 아세토나이트릴(150 mL)을 투입하고 5분 동안 교반하였다. 상기 플라스크에 리튬 하이드라이드(189 mg, 23.7833 mmol)을 투입하고 24시간 동안 교반하였다. 반응이 끝나면 아세토나이트릴을 사용하여 반응 용액을 필터하여 고체를 얻었다. 상기 고체를 승화하여 화합물 2(4.5 g)를 얻었다. (2-hydroxybenzyl)di-p-tolylphosphine oxide (8 g, 23.7833 mmol) prepared in
m/z: 336.13 m/z: 336.13
실시예 3: 화합물 3의 제조Example 3: Preparation of
(단계 1)(Step 1)
플라스크에 디페닐포스피닉 클로라이드(165.2589 mmol, 4.5 eq), 소듐 아이오다이드(165.2589 mmol, 4.5 eq), 및 무수 아세토나이트릴(165 mL, 1 M)을 투입하고 교반하였다. 반응액에 2-하이드록시-4-메틸벤즈알데하이드(5.0 g, 36.7242 mmol, 1.0 eq)을 투입하였다. 반응액을 80℃로 승온하고 24시간 동안 교반하였다. 반응액을 상온으로 냉각하고 30% 과산화수소 수용액(20 mL)을 천천히 투입하였다. 10분 후 소듐 티오설페이트 포화 수용액을 투입하였다. 유기층을 디클로로메탄으로 추출하고 마그네슘 설페이트로 건조하였다. 용매를 감압하여 제거하였다. 실리카겔 컬럼으로 정제하여 (2-하이드록시-4-메틸벤질)디벤질포스핀 옥사이드(9 g)를 얻었다. Diphenylphosphinic chloride (165.2589 mmol, 4.5 eq), sodium iodide (165.2589 mmol, 4.5 eq), and anhydrous acetonitrile (165 mL, 1 M) were added to the flask and stirred. 2-hydroxy-4-methylbenzaldehyde (5.0 g, 36.7242 mmol, 1.0 eq) was added to the reaction solution. The temperature of the reaction solution was raised to 80 °C and stirred for 24 hours. The reaction solution was cooled to room temperature, and 30% hydrogen peroxide aqueous solution (20 mL) was slowly added thereto. After 10 minutes, a saturated aqueous solution of sodium thiosulfate was added. The organic layer was extracted with dichloromethane and dried over magnesium sulfate. The solvent was removed under reduced pressure. Purification by silica gel column gave (2-hydroxy-4-methylbenzyl)dibenzylphosphine oxide (9 g).
(단계 2)(Step 2)
플라스크에 앞서 단계 1에서 제조한 (2-하이드록시-4-메틸벤질)디벤질포스핀 옥사이드(9 g, 27.9208 mmol), 및 무수 아세토나이트릴(180 mL)을 투입하고 5분 동안 교반하였다. 상기 플라스크에 리튬 하이드라이드(221 mg, 27.9208 mmol)을 투입하고 24시간 동안 교반하였다. 반응이 끝나면 아세토나이트릴을 사용하여 반응 용액을 필터하여 고체를 얻었다. 상기 고체를 승화하여 화합물 3(5.5 g)을 얻었다. (2-hydroxy-4-methylbenzyl)dibenzylphosphine oxide (9 g, 27.9208 mmol) prepared in
m/z: 322.11 m/z: 322.11
[실험예][Experimental Example]
실험예 1Experimental Example 1
ITO(indium tin oxide)가 500 Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀리포어사(Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후, 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필, 아세톤의 용제로 초음파 세척을 하고 건조시킨 후, 상기 기판을 5분간 세정한 후 글로브박스로 기판을 수송시켰다.A glass substrate coated with indium tin oxide (ITO) to a thickness of 500 Å was put in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product of Fischer Co. was used as a detergent, and distilled water filtered through a second filter of a product of Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was performed twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with solvents such as isopropyl and acetone, and after drying, the substrate was cleaned for 5 minutes and transported to a glove box.
상기 ITO 투명 전극 위에, 하기 화합물 p-dopant 및 하기 화합물 HIL(2:8의 중량비)를 5 wt%로 사이클로헥사논에 녹인 코팅 조성물을 스핀 코팅(2500 rpm)하고 230℃에서 30분 동안 열처리(경화)하여 1000 Å 두께의 정공주입층을 형성하였다. 상기 정공주입층 위에, 하기 고분자 HTL(Mn: 27,900; Mw: 35,600; Agilent 1200 series를 이용하여 PC 스텐다드(Standard)를 이용한 GPC로 측정)를 2 wt%로 톨루엔에 녹인 코팅 조성물을 스핀 코팅(2500 rpm)하고 230℃에서 20분 동안 열처리하여 1000 Å 두께의 정공수송층을 형성하였다. 상기 정공수송층 위에, 하기 화합물 A와 하기 화합물 Dopant(98:2의 중량비)를 2 wt%로 사이클로헥사논에 녹인 코팅 조성물을 스핀 코팅(2000 rpm)하고 145℃에서 15분 동안 열처리하여 400 Å 두께의 발광층을 형성하였다. On the ITO transparent electrode, a coating composition in which the following compound p-dopant and the following compound HIL (weight ratio of 2:8) were dissolved in cyclohexanone at 5 wt% was spin-coated (2500 rpm) and heat-treated at 230 ° C. for 30 minutes ( curing) to form a hole injection layer having a thickness of 1000 Å. On the hole injection layer, a coating composition in which the following polymer HTL (Mn: 27,900; Mw: 35,600; measured by GPC using PC standard using an Agilent 1200 series) was dissolved in toluene at 2 wt% was spin-coated (2500 rpm) and heat-treated at 230° C. for 20 minutes to form a hole transport layer having a thickness of 1000 Å. On the hole transport layer, spin-coating (2000 rpm) a coating composition in which the following compound A and the following compound Dopant (weight ratio of 98:2) were dissolved in cyclohexanone at 2 wt% and heat-treated at 145 ° C. for 15 minutes to obtain a thickness of 400 Å of the light emitting layer was formed.
상기 발광층 위에, 하기 화합물 ETL과 앞서 실시예 1에서 제조한 화합물(3:7의 중량비)를 2 wt%로 에틸렌글리콜과 1-프로판올(8:2의 부피비)에 녹인 코팅 조성물을 스핀 코팅(2000 rpm)하고 145℃에서 10분 동안 열처리하여 300 Å 두께로 전자 주입 및 수송층을 형성하였다. 상기 전자 주입 및 수송층 위에 1000 Å 두께로 알루미늄을 증착하여 캐소드를 형성하여 유기 발광 소자를 제조하였다.On the light-emitting layer, spin coating a coating composition in which the following compound ETL and the compound prepared in Example 1 (weight ratio of 3:7) were dissolved in 2 wt% of ethylene glycol and 1-propanol (volume ratio of 8:2) were applied (2000 rpm) and heat-treated at 145° C. for 10 minutes to form an electron injection and transport layer with a thickness of 300 Å. An organic light emitting diode was manufactured by depositing aluminum to a thickness of 1000 Å on the electron injection and transport layer to form a cathode.
상기의 과정에서 알루미늄은 2 Å/sec의 증착 속도를 유지하였으며, 증착 시 진공도는 2×10-7 내지 5×10-8 torr를 유지하였다.In the above process, the aluminum deposition rate was maintained at 2 Å/sec, and the vacuum level during deposition was maintained at 2×10 -7 to 5×10 -8 torr.
실험예 2 및 3Experimental Examples 2 and 3
화합물 1 대신 하기 표 1에 기재된 화합물을 사용한 것을 제외하고, 상기 실험예 1과 동일한 방법으로 유기 발광 소자를 제조하였다. An organic light emitting device was manufactured in the same manner as in Experimental Example 1, except that the compound shown in Table 1 was used instead of
비교실험예Comparative Example
화합물 1 대신 화합물 LiQ(8-Quinolinolato Lithium)를 사용한 것을 제외하고, 상기 실험예 1과 동일한 방법으로 유기 발광 소자를 제조하였다. An organic light emitting device was manufactured in the same manner as in Experimental Example 1, except that the compound LiQ (8-Quinolinolato Lithium) was used instead of
상기 실험예 및 비교실험예에서 제조한 유기 발광 소자에 전류를 인가하였을 때, 10 mA/cm2의 전류 밀도에서의 구동 전압, 전류 효율 및 수명을 측정한 결과를 하기 표 1에 나타내었다. 이때, 수명(T90)는 휘도가 초기 휘도(500 nit)에서 90%로 감소하는데 소요되는 시간을 의미한다.When a current was applied to the organic light emitting device prepared in the Experimental Example and Comparative Experimental Example, the driving voltage, current efficiency, and lifetime at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 1 below. At this time, the lifetime T90 means the time required for the luminance to decrease from the initial luminance (500 nit) to 90%.
(V@10mA/cm2)driving voltage
(V@10mA/cm 2 )
(cd/A@10mA/cm2)current efficiency
(cd/A@10mA/cm 2 )
(T90@500 nit)Life (hr)
(T90@500 nits)
상기 표 1에 나타난 바와 같이, 본 발명에 따른 화합물을 사용한 경우 일반적으로 사용되는 화합물 LiQ를 사용한 경우에 비하여 구동 전압이 낮아지고, 전류 효율이 높아지며, 또한 수명이 개선됨을 확인할 수 있었다. As shown in Table 1, when the compound according to the present invention was used, it was confirmed that the driving voltage was lowered, the current efficiency was increased, and the lifespan was improved compared to the case of using the commonly used compound LiQ.
1: 기판
2: 양극
3: 발광층
4: 음극
5: 정공주입층
6: 정공수송층
7: 발광층
8: 전자수송층
9: 전자주입층1: substrate 2: anode
3: light emitting layer 4: cathode
5: hole injection layer 6: hole transport layer
7: light emitting layer 8: electron transport layer
9: electron injection layer
Claims (12)
[화학식 1]
상기 화학식 1에서,
X는 O, 또는 S이고,
Ar1은 치환 또는 비치환된 C6-60 아릴렌이고,
L은 치환 또는 비치환된 C1-10 알킬렌이고,
Ar2는 치환 또는 비치환된 C6-60 아릴이고,
Ar3은 치환 또는 비치환된 C6-60 아릴이다.
A compound represented by Formula 1 below:
[Formula 1]
In Formula 1,
X is O or S;
Ar 1 is a substituted or unsubstituted C 6-60 arylene;
L is a substituted or unsubstituted C 1-10 alkylene;
Ar 2 is a substituted or unsubstituted C 6-60 aryl;
Ar 3 is a substituted or unsubstituted C 6-60 aryl.
Ar1은 비치환되거나, 또는 중수소, C1-60 알킬, 할로겐, -O-Li, 또는 -S-Li로 치환된 C6-20 아릴인,
화합물.
According to claim 1,
Ar 1 is C 6-20 aryl unsubstituted or substituted with deuterium, C 1-60 alkyl, halogen, -O-Li, or -S-Li;
compound.
Ar1은 페닐렌이고,
상기 페닐렌은 비치환되거나, 또는 중수소, 메틸, 에틸, 프로필, 이소프로필, 부틸, 이소부틸, 터트부틸, 플루오로, 클로로, -O-Li, 또는 -S-Li로 치환된,
화합물.
According to claim 1,
Ar 1 is phenylene;
The phenylene is unsubstituted or substituted with deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertbutyl, fluoro, chloro, -O-Li, or -S-Li,
compound.
L은 치환 또는 비치환된 C1-4 알킬렌인,
화합물.
According to claim 1,
L is a substituted or unsubstituted C 1-4 alkylene,
compound.
L은 -CH2-, -CH2CH2-, -CH2CH2CH2-, 또는 -CH2CH2CH2CH2-인,
화합물.
According to claim 1,
L is -CH 2 -, -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -, or -CH 2 CH 2 CH 2 CH 2 -;
compound.
Ar2 및 Ar3은 각각 독립적으로 비치환되거나, 또는 중수소, C1-60 알킬, 또는 할로겐으로 치환된 C6-20 아릴인,
화합물.
According to claim 1,
Ar 2 and Ar 3 are each independently unsubstituted or C 6-20 aryl substituted with deuterium, C 1-60 alkyl, or halogen;
compound.
Ar2 및 Ar3은 페닐이고,
상기 페닐은 비치환되거나, 또는 중수소, 메틸, 에틸, 프로필, 이소프로필, 부틸, 이소부틸, 터트부틸, 플루오로, 또는 클로로로 치환된,
화합물.
According to claim 1,
Ar 2 and Ar 3 are phenyl;
the phenyl is unsubstituted or substituted with deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertbutyl, fluoro, or chloro;
compound.
Ar2 및 Ar3은 서로 동일한,
화합물.
According to claim 1,
Ar 2 and Ar 3 are the same as each other;
compound.
상기 화학식 1은 하기 화학식 1-1로 표시되는,
화합물:
[화학식 1-1]
상기 화학식 1-1에서,
X는 O, 또는 S이고,
R1은 수소, 중수소, C1-60 알킬, 할로겐, -O-Li, 또는 -S-Li이고,
R2 및 R3은 각각 독립적으로, 수소, 중수소, C1-60 알킬, 또는 할로겐이고,
n은 1 내지 10의 정수이다.
According to claim 1,
Formula 1 is represented by the following Formula 1-1,
compound:
[Formula 1-1]
In Formula 1-1,
X is O or S;
R 1 is hydrogen, deuterium, C 1-60 alkyl, halogen, -O-Li, or -S-Li;
R 2 and R 3 are each independently hydrogen, deuterium, C 1-60 alkyl, or halogen;
n is an integer from 1 to 10;
상기 화학식 1로 표시되는 화합물은 하기로 구성되는 군으로부터 선택되는 어느 하나인,
화합물:
According to claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of
compound:
a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound according to any one of claims 1 to 10. That is, an organic light emitting device.
상기 화합물을 포함하는 유기물층은 전자수송층 또는 전자주입층인,
유기 발광 소자.
According to claim 11,
The organic material layer containing the compound is an electron transport layer or an electron injection layer,
organic light emitting device.
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