KR20220098454A - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents
An electroluminescent compound and an electroluminescent device comprising the same Download PDFInfo
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- KR20220098454A KR20220098454A KR1020210000200A KR20210000200A KR20220098454A KR 20220098454 A KR20220098454 A KR 20220098454A KR 1020210000200 A KR1020210000200 A KR 1020210000200A KR 20210000200 A KR20210000200 A KR 20210000200A KR 20220098454 A KR20220098454 A KR 20220098454A
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- 229910052727 yttrium Inorganic materials 0.000 description 1
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H01L51/5012—
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- H01L51/5056—
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- H01L51/5072—
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- 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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- 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]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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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]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
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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]
- H10K50/17—Carrier injection layers
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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]
- H10K50/18—Carrier blocking layers
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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
- H10K50/80—Constructional details
- H10K50/85—Arrangements for extracting light from the devices
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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
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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Abstract
Description
본 발명은 유기발광 화합물에 관한 것으로서, 더욱 상세하게는 유기발광소자에 구비되는 광효율 개선층 (Capping layer) 재료로 채용되는 것을 특징으로 하는 유기발광 화합물과 이를 채용하여 소자의 저전압 구동과 발광 효율 특성이 현저히 향상된 유기발광소자에 관한 것이다.The present invention relates to an organic light emitting compound, and more particularly, to an organic light emitting compound, characterized in that it is employed as a light efficiency improving layer (capping layer) material provided in an organic light emitting device, and low voltage driving and light emitting efficiency characteristics of the device by employing the same It relates to this remarkably improved organic light emitting device.
유기발광소자는 투명 기판 위에도 소자를 형성할 수 있을 뿐 아니라, 플라즈마 디스플레이 패널 (Plasma Display Panel)이나 무기전계발광 (EL) 디스플레이에 비해 10 V 이하의 저전압 구동이 가능하고, 전력 소모가 비교적 적으며, 색감이 뛰어나다는 장점이 있고, 녹색, 청색, 적색의 3가지 색을 나타낼 수가 있어 최근에 차세대 디스플레이 소자로 많은 관심의 대상이 되고 있다.The organic light emitting device can be formed on a transparent substrate as well as being able to drive at a low voltage of 10 V or less compared to a plasma display panel or an inorganic electroluminescence (EL) display, and consume relatively little power. , has the advantage of excellent color, and can represent three colors of green, blue, and red, and has recently become a subject of much interest as a next-generation display device.
다만, 이러한 유기발광소자가 상기와 같은 특징으로 발휘하기 위해서는 소자 내 유기층을 이루는 물질인 정공주입 물질, 정공수송 물질, 발광물질, 전자수송 물질, 전자주입 물질 등이 안정하고 효율적인 재료에 의하여 뒷받침되는 것이 선행되어야 하나, 아직까지는 안정하고 효율적인 유기발광소자용 유기층 재료의 개발이 충분히 이루어지지 않은 상태이다.However, in order for such an organic light emitting device to exhibit the above characteristics, a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc. However, the development of a stable and efficient organic layer material for an organic light emitting device has not yet been sufficiently developed.
따라서, 더욱 안정적인 유기발광소자를 구현하고, 소자의 고효율, 장수명, 대형화 등을 위해서는 효율 및 수명 특성 측면에서 추가적인 개선이 요구되고 있는 상황이고, 특히 유기발광소자의 각 유기층을 이루는 소재에 대한 개발이 절실히 필요한 실정이다.Therefore, in order to realize a more stable organic light emitting device, and to achieve high efficiency, long lifespan, and large size of the device, additional improvements are required in terms of efficiency and lifespan characteristics. It is desperately needed.
이와 관련하여 최근에 상기 유기발광소자의 구조 중 정공수송층 소재에 대하여는 기존 유기 소재의 도전율 (mobility)을 향상시키기 위한 연구가 활발히 이루어지고 있다.In this regard, recently, with respect to the material of the hole transport layer in the structure of the organic light emitting device, research for improving the conductivity of the existing organic material has been actively conducted.
또한, 최근에는 각 유기층 재료의 성능 변화를 주어 유기발광소자의 특성을 향상시키는 연구뿐만 아니라, 애노드 (anode)와 캐소드 (cathode) 사이에서 최적화된 광학 두께에 의한 색순도 향상 및 발광 효율 증대 기술이 소자 성능을 향상시키는데 중요한 요소 중의 하나로 착안되고 있으며, 이러한 방법의 일 예로 전극에 캡핑층 (capping layer)을 사용하여 광효율 증가와 우수한 색순도를 거두기도 한다.In addition, in recent years, research on improving the characteristics of an organic light emitting device by giving a change in the performance of each organic layer material, as well as a technology for improving color purity and increasing luminous efficiency by an optical thickness optimized between an anode and a cathode has been developed. It has been focused on one of the important factors for improving the performance, and as an example of this method, an increase in light efficiency and excellent color purity are achieved by using a capping layer on an electrode.
따라서, 본 발명은 유기발광소자에 구비되는 광효율 개선층에 채용되어 향상된 소자의 저전압 구동과 우수한 발광 효율 특성을 구현할 수 있는 신규한 유기발광 화합물 및 이를 포함하는 유기발광소자를 제공하고자 한다.Accordingly, an object of the present invention is to provide a novel organic light emitting compound which is employed in a light efficiency improving layer provided in an organic light emitting device to realize improved low voltage driving and excellent light emitting efficiency characteristics of the device, and an organic light emitting device including the same.
본 발명은 상기 과제를 해결하기 위하여, 하기 [화학식 Ⅰ]로 표시되는 화합물 중에서 선택된 어느 하나의 유기발광 화합물을 제공한다.In order to solve the above problems, the present invention provides any one organic light emitting compound selected from the compounds represented by the following [Formula I].
[화학식 Ⅰ][Formula Ⅰ]
상기 [화학식 Ⅰ]의 특징적인 구조와 이에 의해서 구현되는 구체적인 화합물, 그리고 X, R, R1 내지 R4에 대해서는 후술하기로 한다.The characteristic structure of the [Formula I] and specific compounds implemented thereby, and X, R, R 1 to R 4 will be described later.
본 발명에 따른 화합물을 유기발광소자에 구비되는 광효율 개선층 재료로 채용할 경우에 향상된 소자의 저전압 구동 특성, 그리고 우수한 발광 효율을 구현할 수 있어 다양한 디스플레이 소자에 유용하게 사용될 수 있다.When the compound according to the present invention is employed as a material for a light efficiency improvement layer provided in an organic light emitting device, it is possible to realize improved low voltage driving characteristics and excellent luminous efficiency of the device, so that it can be usefully used in various display devices.
이하, 본 발명을 더욱 상세하게 설명한다.Hereinafter, the present invention will be described in more detail.
본 발명은 유기발광소자의 향상된 저전압 구동 특성 및 우수한 발광 효율을 거둘 수 있는 하기 [화학식 Ⅰ]로 표시되는 유기발광 화합물에 관한 것이다.The present invention relates to an organic light emitting compound represented by the following [Formula I], which can achieve improved low voltage driving characteristics and excellent luminous efficiency of an organic light emitting diode.
본 발명에 따른 [화학식 Ⅰ]로 표시되는 유기발광 화합물은 구조적으로 하기 [화학식 Ⅰ]로 표시되는 골격과 같이 하나 이상의 퓨란 및/또는 티오펜에 특징적 치환기 (R1 내지 R4)가 특정 위치에 치환된 페닐기를 도입한 것을 특징으로 하고, 이를 통하여 본 발명에 따른 화합물을 광효율 개선층에 채용하여 향상된 저전압 구동 및 우수한 발광 효율을 갖는 유기발광소자를 구현할 수 있다.The organic light emitting compound represented by [Formula I] according to the present invention is structurally, as in the skeleton represented by the following [Formula I], characteristic substituents (R 1 to R 4 ) in one or more furan and / or thiophene at a specific position It is characterized in that a substituted phenyl group is introduced, and through this, an organic light emitting device having improved low voltage driving and excellent luminous efficiency can be realized by employing the compound according to the present invention in the light efficiency improving layer.
[화학식 Ⅰ][Formula Ⅰ]
상기 [화학식 Ⅰ]에서,In the above [Formula I],
X는 O 또는 S이고, m은 1 내지 3의 정수이며, 상기 m이 2이상인 경우 복수 개의 [ ] 내 구조체는 서로 동일하거나 상이하다. 즉 본 발명에 따른 화합물은 하나 이상의 퓨란 및/또는 티오펜에 치환된 페닐기가 도입된 것을 특징으로 한다.X is O or S, m is an integer of 1 to 3, and when m is 2 or more, a plurality of structures in [ ] are the same or different from each other. That is, the compound according to the present invention is characterized in that a phenyl group substituted with one or more furan and/or thiophene is introduced.
R은 각각 독립적으로 수소, 중수소, 할로겐기, 시아노기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기, 치환 또는 비치환된 탄소수 1 내기 20의 알콕시기, 치환 또는 비치환된 탄소수 1 내지 20의 할로겐화된 알킬기, 치환 또는 비치환된 탄소수 1 내지 20의 중수소화된 알킬기, 치환 또는 비치환된 탄소수 1 내지 20의 할로겐화된 알콕시기, 치환 또는 비치환된 탄소수 1 내지 20의 중수소화된 알콕시기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬실릴기 및 치환 또는 비치환된 탄소수 6 내지 30의 아릴실릴기 중에서 선택되며, n은 0 내지 2의 정수이며, 상기 n이 2인 경우 R이 복수 개인 경우 서로 동일하거나 상이하다.R is each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 Alkoxy group, substituted or unsubstituted halogenated alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted deuterated alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted halogenated alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted A substituted or unsubstituted C1 to C20 deuterated alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 It is selected from an alkylsilyl group and a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, n is an integer of 0 to 2, and when n is 2, when plural R is the same or different from each other.
R1 내지 R4는 서로 동일하거나 상이하고, 각각 독립적으로 중수소, 시아노기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 치환 또는 비치환된 탄소수 1 내지 20의 할로겐화된 알킬기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬실릴기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴실릴기, 치환 또는 비치환된 나프틸, 치환 또는 비치환된 플루오렌, 치환 또는 비치환된 벤조옥사졸, 치환 또는 비치환된 벤조티아졸, 치환 또는 비치환된 다이벤조퓨란 및 치환 또는 비치환된 다이벤조티오펜 중에서 선택된다.R 1 to R 4 are the same as or different from each other, and each independently represents a deuterium, a cyano group, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 1 to C 20 halogenated alkyl group, a substituted or unsubstituted an alkylsilyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorene, a substituted or unsubstituted benzoxazole, a substituted or unsubstituted benzothiazole, substituted or unsubstituted dibenzofuran and substituted or unsubstituted dibenzothiophene.
한편, 상기 R 및 R1 내지 R4의 정의에서, '치환 또는 비치환된'이라 함은 중수소, 할로겐기, 시아노기, 니트로기, 히드록시기, 실릴기, 알킬기, 시클로알킬기, 알콕시기, 알케닐기, 아릴기 및 헤테로아릴기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되거나, 상기 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다.Meanwhile, in the definitions of R and R 1 to R 4 , 'substituted or unsubstituted' means deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a silyl group, an alkyl group, a cycloalkyl group, an alkoxy group, an alkenyl group. , means substituted with one or two or more substituents selected from the group consisting of an aryl group and a heteroaryl group, or substituted with a substituent to which two or more of the substituents are connected, or does not have any substituents.
본 발명에 있어서, 상기 치환기들의 예시들에 대해서 아래에서 구체적으로 설명하나, 이에 한정되는 것은 아니며, 본 발명에 따른 구체적인 화합물에서 명확히 확인할 수 있다.In the present invention, examples of the substituents will be described in detail below, but the present invention is not limited thereto, and can be clearly identified in the specific compound according to the present invention.
본 발명에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 20인 것이 바람직하다. 구체적인 예로는 메틸기, 에틸기, 프로필기, n-프로필기, 이소프로필기, 부틸기, n-부틸기, 이소부틸기, tert-부틸기, sec-부틸기, 1-메틸-부틸기, 1-에틸-부틸기, 펜틸기, n-펜틸기, 이소펜틸기, 네오펜틸기, tert-펜틸기, 헥실기, n-헥실기, 1-메틸펜틸기, 2-메틸펜틸기, 4-메틸-2-펜틸기, 3,3-디메틸부틸기, 2-에틸부틸기, 헵틸기, n-헵틸기, 1-메틸헥실기, 시클로펜틸메틸기, 시클로헥틸메틸기, 옥틸기, n-옥틸기, tert-옥틸기, 1-메틸헵틸기, 2-에틸헥실기, 2-프로필펜틸기, n-노닐기, 2,2-디메틸헵틸기, 1-에틸-프로필기, 1,1-디메틸-프로필기, 이소헥실기, 2-메틸펜틸기, 4-메틸헥실기, 5-메틸헥실기 등이 있으나, 이들에 한정되지 않는다.In the present invention, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 20. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert -Octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, and the like, but is not limited thereto.
본 발명에 있어서, 알콕시기는 직쇄 또는 분지쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 입체적 방해를 주지 않는 범위인 1 내지 20개인 것이 바람직하다. 구체적으로, 메톡시기, 에톡시기, n-프로폭시기, 이소프로폭시기, i-프로필옥시기, n-부톡시기, 이소부톡시기, tert-부톡시기, sec-부톡시기, n-펜틸옥시기, 네오펜틸옥시기, 이소펜틸옥시기, n-헥실옥시기, 3,3-디메틸부틸옥시기, 2-에틸부틸옥시기, n-옥틸옥시기, n-노닐옥시기, n-데실옥시기, 벤질옥시기, p-메틸벤질옥시기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present invention, the alkoxy group may be straight-chain or branched. Although the number of carbon atoms of the alkoxy group is not particularly limited, it is preferably 1 to 20, which is a range that does not cause steric hindrance. Specifically, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, i-propyloxy group, n-butoxy group, isobutoxy group, tert-butoxy group, sec-butoxy group, n-pentyloxy group , neopentyloxy group, isopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group , a benzyloxy group, a p-methylbenzyloxy group, etc., but is not limited thereto.
본 발명에 있어서, 아릴기는 단환식 또는 다환식일 수 있고, 탄소수는 특별히 한정되지 않으나 6 내지 30인 것이 바람직하다. 단환식 아릴기의 예로는 페닐기, 비페닐기, 터페닐기, 스틸벤기 등이 있고, 다환식 아릴기의 예로는 나프틸기, 안트라세닐기, 페난트레닐기, 파이레닐기, 페릴레닐기, 테트라세닐기, 크라이세닐기, 플루오레닐기, 아세나프타센닐기, 트리페닐렌기, 플루오안트렌(fluoranthrene)기 등이 있으나, 본 발명의 범위가 이들 예로만 한정되는 것은 아니다.In the present invention, the aryl group may be monocyclic or polycyclic, and the number of carbon atoms is not particularly limited, but is preferably 6 to 30. Examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and a stilbene group, and examples of the polycyclic aryl group include a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, tetracenyl group. , chrysenyl group, fluorenyl group, acenaphthacenyl group, triphenylene group, fluoranthrene group, etc., but the scope of the present invention is not limited to these examples.
본 발명에 있어서, 플루오렌 (플루오레닐기)는 2개의 고리 유기화합물이 1개의 원자를 통하여 연결된 구조로서, 예로는 
본 발명에 있어서, 플루오레닐기는 열린 플루오레닐기의 구조를 포함하며, 여기서 열린 플루오레닐기는 2개의 고리 유기화합물이 1개의 원자를 통하여 연결된 구조에서 한쪽 고리 화합물의 연결이 끊어진 상태의 구조로서, 예로는 
본 발명에 있어서, 헤테로아릴기는 이종원자로 O, N 또는 S를 포함하는 헤테로고리기로서, 탄소수는 특별히 한정되지 않으나 탄소수 2 내지 30인 것이 바람직하며, 본 발명에서 이의 구체적인 예를 들면, 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기, 트리아졸기, 아크리딜기, 피리다진기, 피라지닐기, 퀴놀리닐기, 퀴나졸린기, 퀴녹살리닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤조옥사졸기, 벤조이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 디벤조퓨라닐기, 페난트롤린기, 티아졸릴기, 이소옥사졸릴기, 옥사디아졸릴기, 티아디아졸릴기, 벤조티아졸릴기, 페노티아지닐기, 페녹사진기, 페노티아진기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present invention, the heteroaryl group is a heterocyclic group containing O, N or S as a heteroatom, and the number of carbon atoms is not particularly limited, but preferably has 2 to 30 carbon atoms, and a specific example thereof in the present invention is a thiophene group , furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, acridyl group, pyridazine group, pyra Zinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxa Zol group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, dibenzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadia and a zolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, a phenoxazine group, a phenothiazine group, and the like, but are not limited thereto.
본 발명에 있어서, 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다.In the present invention, the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, the present invention is not limited thereto.
본 발명에서 사용되는 치환기인 할로겐기의 구체적인 예로는 플루오르(F), 클로린(Cl), 브롬(Br) 등을 들 수 있다.Specific examples of the halogen group as a substituent used in the present invention include fluorine (F), chlorine (Cl), bromine (Br), and the like.
상기 [화학식 Ⅰ]로 표시되는 본 발명에 따른 유기발광 화합물은 그 구조적 특이성으로 인하여 유기발광소자에 구비되는 광효율 개선층 재료로 사용될 수 있다.The organic light emitting compound according to the present invention represented by the [Formula I] may be used as a material for the light efficiency improving layer provided in the organic light emitting device due to its structural specificity.
본 발명에 따른 [화학식 Ⅰ]로 표시되는 유기발광 화합물의 바람직한 구체예로는 하기 화합물들이 있으나, 이들에만 한정되는 것은 아니다.Preferred examples of the organic light emitting compound represented by [Formula I] according to the present invention include the following compounds, but are not limited thereto.
이와 같이, 본 발명에 따른 유기발광 화합물은 고유의 특성을 발휘하는 특징적인 골격과 이에 도입되는 고유의 특성을 갖는 모이어티 (moiety)를 이용하여 다양한 특성을 갖는 유기발광 화합물을 합성할 수 있고, 그 결과 본 발명에 따른 유기발광 화합물을 발광층, 광효율 개선층, 정공수송층, 전자수송층, 전자저지층, 정공저지층 등 다양한 유기층 물질로 적용할 수 있으며, 본 발명의 바람직한 실시예에 의하면 유기발광소자에 구비되는 광효율 개선층에 적용하여 소자의 발광효율 등의 발광 특성을 더욱 향상시킬 수 있다.As such, the organic light emitting compound according to the present invention can synthesize an organic light emitting compound having various characteristics using a characteristic skeleton exhibiting unique properties and a moiety having intrinsic properties introduced thereto, As a result, the organic light emitting compound according to the present invention can be applied to various organic layer materials such as a light emitting layer, a light efficiency improving layer, a hole transport layer, an electron transport layer, an electron blocking layer, and a hole blocking layer, and according to a preferred embodiment of the present invention, an organic light emitting device It is possible to further improve the light-emitting characteristics such as the light-emitting efficiency of the device by applying to the light-efficiency improvement layer provided in the device.
또한, 본 발명의 화합물은 일반적인 유기발광소자 제조방법에 따라 소자에 적용할 수 있다.In addition, the compound of the present invention can be applied to a device according to a general method for manufacturing an organic light emitting device.
본 발명의 일 실시예에 따른 유기발광소자는 제1 전극과 제2 전극 및 이 사이에 배치된 유기층을 포함하는 구조로 이루어질 수 있으며, 본 발명에 따른 유기발광 화합물을 소자의 유기층에 사용한다는 것을 제외하고는 통상의 소자 제조방법 및 재료를 사용하여 제조될 수 있다.The organic light emitting device according to an embodiment of the present invention may have a structure including a first electrode and a second electrode and an organic layer disposed therebetween. Except that, it may be manufactured using conventional device manufacturing methods and materials.
본 발명에 따른 유기발광소자의 유기층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 정공 주입층, 정공 수송층, 발광층, 전자 수송층, 전자 주입층, 전자 저지층, 정공 저지층, 광효율 개선층 (Capping layer) 등을 포함하는 구조를 가질 수 있다. 그러나, 이에 한정되지 않고 더 적은 수, 더 많은 수의 유기층을 포함할 수도 있다.The organic layer of the organic light emitting device according to the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic layers are stacked. For example, it 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, an electron blocking layer, a hole blocking layer, a light efficiency improving layer (Capping layer), and the like. However, the present invention is not limited thereto and may include a smaller number or a larger number of organic layers.
또한, 본 발명의 일 실시예에 따른 유기전기발광소자는 기판, 제1전극 (양극), 유기층, 제2전극 (음극) 및 광효율 개선층을 포함하며, 상기 광효율 개선층은 제1 전극 하부 (Bottom emission) 또는 제2 전극 상부 (Top emission)에 형성될 수 있다.In addition, the organic electroluminescent device according to an embodiment of the present invention includes a substrate, a first electrode (anode), an organic layer, a second electrode (cathode) and a light efficiency improving layer, wherein the light efficiency improving layer is a lower portion of the first electrode ( Bottom emission) or on the second electrode top (Top emission).
제2 전극 상부 (Top emission)에 형성되는 방식은 발광층에서 형성된 빛이 캐소드쪽으로 방출되는데 캐소드쪽으로 방출되는 빛이 굴절률이 상대적으로 높은 본 발명에 따른 화합물로 형성된 광효율 개선층 (CPL)을 통과하면서 빛의 파장이 증폭되고 따라서 광효율이 상승하게 된다 또한, 제1 전극 하부 (Bottom emission)에 형성되는 방식 역시 마찬가지 원리에 의해 본 발명에 따른 화합물을 광효율 개선층에 채용하여 유기전기소자의 광효율이 향상된다.In the method of forming the second electrode on top (Top emission), the light formed in the light emitting layer is emitted toward the cathode, and the light emitted toward the cathode passes through the light efficiency improvement layer (CPL) formed of the compound according to the present invention having a relatively high refractive index. The wavelength of is amplified and thus the light efficiency is increased .
본 발명에 따른 바람직한 유기발광소자의 유기층 구조 등에 대해서는 후술하는 실시예에서 보다 상세하게 설명한다.The organic layer structure of the preferred organic light emitting device according to the present invention will be described in more detail in the following Examples.
또한, 본 발명에 따른 유기발광소자는 스퍼터링 (sputtering)이나 전자빔 증발 (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, 전자 수송층을 포함하는 유기층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다.In addition, the organic light emitting diode according to the present invention is a metal or conductive metal oxide or an alloy thereof on a substrate by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation. It can be prepared by depositing an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기층, 양극 물질을 차례로 증착시켜 유기발광소자를 만들 수도 있다. 상기 유기층은 정공 주입층, 정공 수송층, 발광층 및 전자 수송층 등을 포함하는 다층 구조일 수도 있으나, 이에 한정되지 않고 단층 구조일 수 있다. 또한, 상기 유기층은 다양한 고분자 소재를 사용하여 증착법이 아닌 솔벤트 프로세스(solvent process), 예컨대 스핀 코팅, 딥 코팅, 닥터 블레이딩, 스크린 프린팅, 잉크젯 프린팅 또는 열 전사법 등의 방법에 의하여 더 적은 수의 층으로 제조할 수 있다.In addition to this method, an organic light emitting diode may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate. The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. In addition, the organic layer can be formed in a smaller number by a solvent process rather than a deposition method using various polymer materials, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method. It can be made in layers.
상기 양극 물질로는 통상 유기층으로 정공주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 본 발명에서 사용될 수 있는 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금, 아연 산화물, 인듐 산화물, 인듐 주석 산화물(ITO), 인듐 아연 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](PEDT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.As the anode material, a material having a large work function is generally preferred so that holes can be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc. Metal oxides, combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT) , a conductive polymer such as polypyrrole and polyaniline, but is not limited thereto.
상기 음극 물질로는 통상 유기층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 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 to facilitate electron injection into the organic layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof, and multilayers such as LiF/Al or LiO 2 /Al Structural materials and the like, but are not limited thereto.
정공 주입 물질로는 낮은 전압에서 양극으로부터 정공을 잘 주입받을 수 있는 물질로서, 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린(porphyrine), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴 헥사아자트리페닐렌, 퀴나크리돈(quinacridone) 계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.The hole injection material is a material capable of well injecting holes from the anode at a low voltage, and 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. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene, quinacridone-based organic material, perylene-based organic material, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.
정공 수송 물질로는 양극이나 정공 주입층으로부터 정공을 수송 받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 본 발명에 따른 유기발광 화합물을 이용하여 소자의 저전압 구동 특성, 발광효율 및 수명 특성을 더욱 향상시킬 수 있다.As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer is suitable, and a material having high hole mobility is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together. can be further improved.
발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자효율이 좋은 물질이 바람직하다. 구체적인 예로는 8-히드록시-퀴놀린 알루미늄 착물(Alq3), 카르바졸 계열 화합물, 이량체화 스티릴(dimerized styryl) 화합물, BAlq, 10-히드록시벤조 퀴놀린-금속 화합물, 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물, 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자, 스피로(spiro) 화합물, 폴리플루오렌, 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다.The light-emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ), carbazole-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole, benzthiazole and There are benzimidazole-based compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene, rubrene, and the like, but is not limited thereto.
전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 Al 착물, Alq3를 포함한 착물, 유기 라디칼 화합물, 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다.As the electron transport material, a material capable of well injecting electrons from the cathode and transferring them to the light emitting layer, and a material having high electron mobility is suitable. Specific examples include, but are not limited to, an Al complex of 8-hydroxyquinoline, a complex including Alq 3 , an organic radical compound, and a hydroxyflavone-metal complex.
본 발명에 따른 유기발광소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light emitting diode according to the present invention may be a top emission type, a back emission type, or a double-sided emission type depending on the material used.
또한, 본 발명에 따른 유기발광 화합물은 유기 태양 전지, 유기 감광체, 유기 트랜지스터 등을 비롯한 유기 전자 소자에서도 유기발광소자에 적용되는 것과 유사한 원리로 작용할 수 있다.In addition, the organic light emitting compound according to the present invention may act on a principle similar to that applied to the organic light emitting device in organic electronic devices including organic solar cells, organic photoreceptors, organic transistors, and the like.
이하, 바람직한 실시예를 들어 본 발명을 더욱 상세하게 설명한다. 그러나, 이들 실시예는 본 발명을 보다 구체적으로 설명하기 위한 것으로, 본 발명의 범위가 이에 의하여 제한되지 않고, 본 발명의 범주 및 기술사상 범위 내에서 다양한 변경 및 수정이 가능함은 당업계의 통상의 지식을 가진 자에게 자명할 것이다.Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are for explaining the present invention in more detail, the scope of the present invention is not limited thereby, and it is common in the art that various changes and modifications are possible within the scope and spirit of the present invention. It will be self-evident to those with knowledge.
합성예Synthesis example 1 : 화합물 18의 합성 1: Synthesis of compound 18
(1) (One) 제조예production example 1 : 중간체 18-1의 합성 1: Synthesis of Intermediate 18-1
2,5-Dibromothiophene (10.0 g, 0.041 mol), 3,5-Dichlorophenylboronic acid (18.9 g, 0.099 mol), Pd(PPh3)4 (2.9 g, 0.003 mol)에 THF를 넣고 교반하였다. 그 후, H2O에 녹인 NaOH (9.9 g, 0.248 mol)를 첨가하여 65 ℃에서 6시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 18-1>을 11.2 g (수율 72.4%) 수득하였다.2,5-Dibromothiophene (10.0 g, 0.041 mol), 3,5-Dichlorophenylboronic acid (18.9 g, 0.099 mol), Pd(PPh 3 ) 4 (2.9 g, 0.003 mol) was added with THF and stirred. Then, NaOH (9.9 g, 0.248 mol) dissolved in H 2 O was added, and the reaction was stirred at 65° C. for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 11.2 g (yield 72.4%) of <Intermediate 18-1>.
(2) (2) 제조예production example 2 : 화합물 18의 합성 2: Synthesis of compound 18
중간체 18-1 (10.0 g, 0.027 mol), 1-Naphthylboronic acid (22.1 g, 0.128 mol), K2CO3 (44.3 g, 0.321 mol), 촉매 Pd(OAc)2 (3.1 g, 0.003 mol), 리간드 X-Phos (1.3 g, 0.003 mol), THF 200 mL와 H2O 50 mL, ethanol 50 mL를 넣고 90 ℃에서 6시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 18>을 13.3 g (수율 67.2%) 수득하였다.Intermediate 18-1 (10.0 g, 0.027 mol), 1-Naphthylboronic acid (22.1 g, 0.128 mol), K 2 CO 3 (44.3 g, 0.321 mol), catalyst Pd(OAc) 2 (3.1 g, 0.003 mol), Ligand X-Phos (1.3 g, 0.003 mol), 200 mL of THF, 50 mL of H 2 O, and 50 mL of ethanol were added, and the reaction was stirred at 90 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 13.3 g (yield 67.2%) of <Compound 18>.
LC/MS: m/z=740[(M+1)+]LC/MS: m/z=740[(M+1) + ]
합성예Synthesis example 2 : 화합물 29의 합성 2: Synthesis of compound 29
(1) (One) 제조예production example 1 : 화합물 29의 합성 1: Synthesis of compound 29
중간체 18-1 (10.0 g, 0.027 mol), 4-(Dibenzofuranyl)boronic acid (27.2 g, 0.128 mol), K2CO3 (44.3 g, 0.321 mol), 촉매 Pd(OAc)2 (3.1 g, 0.003 mol), 리간드 X-Phos (1.3 g, 0.003 mol), THF 200 mL와 H2O 50 mL, ethanol 50 mL를 넣고 90 ℃에서 6시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 29>를 15.2 g (수율 63.1%) 수득하였다.Intermediate 18-1 (10.0 g, 0.027 mol), 4-(Dibenzofuranyl)boronic acid (27.2 g, 0.128 mol), K 2 CO 3 (44.3 g, 0.321 mol), catalyst Pd(OAc) 2 (3.1 g, 0.003 mol), ligand X-Phos (1.3 g, 0.003 mol), THF 200 mL, H 2 O 50 mL, and ethanol 50 mL were added and reacted by stirring at 90 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 15.2 g (yield 63.1%) of <Compound 29>.
LC/MS: m/z=900[(M+1)+]LC/MS: m/z=900[(M+1) + ]
합성예Synthesis example 3 : 화합물 131의 합성 3: Synthesis of compound 131
(1) (One) 제조예production example 1 : 중간체 131-1의 합성 1: Synthesis of intermediate 131-1
5,5'-Dibromo-2,2'-bithiophene (10.0 g, 0.031 mol), 3,5-Dichlorophenylboronic acid (14.1 g, 0.074 mol), Pd(PPh3)4 (2.1 g, 0.002 mol)에 THF를 넣고 교반하였다. 그 후, H2O에 녹인 NaOH (7.4 g, 0.185 mol)를 첨가하여 65 ℃에서 6시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼하여 <중간체 131-1>을 9.6 g (수율 68.2%) 수득하였다.THF in 5,5'-Dibromo-2,2'-bithiophene (10.0 g, 0.031 mol), 3,5-Dichlorophenylboronic acid (14.1 g, 0.074 mol), Pd(PPh 3 ) 4 (2.1 g, 0.002 mol) was added and stirred. Then, NaOH (7.4 g, 0.185 mol) dissolved in H 2 O was added, and the reaction was stirred at 65° C. for 6 hours. After completion of the reaction, the mixture was extracted and concentrated, and then columned to obtain 9.6 g of <Intermediate 131-1> (yield 68.2%).
(2) (2) 제조예production example 2 : 중간체 131-2의 합성 2: Synthesis of intermediate 131-2
중간체 131-1 (10.0 g, 0.022 mol), Bis(pinacolato)diboron (26.7 g, 0.105 mol), KOAc (17.2 g, 0.175 mol), Pd(dppf)Cl2 (0.5 g, 0.001 mol)에 dioxane 200 mL 넣고 100 ℃에서 12시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 131-2>를 13.2 g (수율 73.2%) 수득하였다.Intermediate 131-1 (10.0 g, 0.022 mol), Bis(pinacolato)diboron (26.7 g, 0.105 mol), KOAc (17.2 g, 0.175 mol), Pd(dppf)Cl 2 (0.5 g, 0.001 mol) dioxane 200 mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 13.2 g (yield 73.2%) of <Intermediate 131-2>.
(3) (3) 제조예production example 3 : 화합물 131의 합성 3: Synthesis of compound 131
중간체 131-2 (10.0 g, 0.012 mol), 2-Bromo-1,3-benzoxazole (11.6 g, 0.058 mol), K2CO3 (20.2 g, 0.146 mol), Pd(PPh3)4 (0.3 g, 0.0002 mol), Toluene 200 mL, Ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 131>을 6.5 g (수율 67.9%) 수득하였다.Intermediate 131-2 (10.0 g, 0.012 mol), 2-Bromo-1,3-benzoxazole (11.6 g, 0.058 mol), K 2 CO 3 (20.2 g, 0.146 mol), Pd(PPh 3 ) 4 (0.3 g , 0.0002 mol), Toluene 200 mL, Ethanol 50 mL, H 2 O 50 mL, and stirred at 100 °C for 6 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 6.5 g (yield 67.9%) of <Compound 131>.
LC/MS: m/z=786[(M+1)+]LC/MS: m/z=786[(M+1) + ]
합성예Synthesis example 4 : 화합물 205의 합성 4: Synthesis of compound 205
(1) (One) 제조예production example 1 : 중간체 205-1의 합성 1: Synthesis of Intermediate 205-1
2,5-Dibromofuran (10.0 g, 0.044 mol), 3,5-Dichlorophenylboronic acid (20.3 g, 0.106 mol), Pd(PPh3)4 (3.1 g, 0.003 mol)에 THF를 넣고 교반하였다. 그 후, H2O에 녹인 NaOH (10.6 g, 0.266 mol)를 첨가하여 65 ℃에서 6시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼하여 <중간체 205-1>을 11.8 g (수율 74.4%) 수득하였다.2,5-Dibromofuran (10.0 g, 0.044 mol), 3,5-Dichlorophenylboronic acid (20.3 g, 0.106 mol), Pd(PPh 3 ) 4 (3.1 g, 0.003 mol) was added with THF and stirred. Then, NaOH (10.6 g, 0.266 mol) dissolved in H 2 O was added, and the reaction was stirred at 65° C. for 6 hours. After completion of the reaction, 11.8 g (yield 74.4%) of <Intermediate 205-1> was obtained by extraction and concentration by column.
(2) (2) 제조예production example 2 : 중간체 205-2의 합성 2: Synthesis of Intermediate 205-2
1-Bromo-4-tert-butylnaphthalene (10.0 g, 0.038 mol), Bis(pinacolato)diboron (11.6 g, 0.046 mol), KOAc (7.5 g, 0.076 mol), Pd(dppf)Cl2 (0.8 g, 0.001 mol)에 dioxane 200 mL 넣고 100 ℃에서 12시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 205-2>를 9.1 g (수율 77.2%) 수득하였다.1-Bromo-4-tert-butylnaphthalene (10.0 g, 0.038 mol), Bis(pinacolato)diboron (11.6 g, 0.046 mol), KOAc (7.5 g, 0.076 mol), Pd(dppf)Cl 2 (0.8 g, 0.001) mol) into 200 mL of dioxane and stirred at 100 °C for 12 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 9.1 g (yield 77.2%) of <Intermediate 205-2>.
(3) (3) 제조예production example 3 : 화합물 205의 합성 3: Synthesis of compound 205
중간체 205-1 (10.0 g, 0.028 mol), 중간체 205-2 (41.6 g, 0.134 mol), K2CO3 (46.3 g, 0.335mol), 촉매 Pd(OAc)2 (3.2 g, 0.003 mol), 리간드 X-Phos (1.3 g, 0.003 mol), THF 200 mL와 H2O 50 mL와 ethanol 50 mL를 넣고 90 ℃에서 6시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 205>를 15.3 g (수율 57.7%) 수득하였다.Intermediate 205-1 (10.0 g, 0.028 mol), Intermediate 205-2 (41.6 g, 0.134 mol), K 2 CO 3 (46.3 g, 0.335 mol), Catalyst Pd(OAc) 2 (3.2 g, 0.003 mol), Ligand X-Phos (1.3 g, 0.003 mol), 200 mL of THF, 50 mL of H 2 O, and 50 mL of ethanol were added, and the reaction was stirred at 90 °C for 6 hours. After completion of the reaction, 15.3 g (yield 57.7%) of <Compound 205> was obtained by extraction and concentration, followed by column and recrystallization.
LC/MS: m/z=948[(M+1)+]LC/MS: m/z=948[(M+1) + ]
합성예Synthesis example 5 : 화합물 238의 합성 5: Synthesis of compound 238
(1) (One) 제조예production example 1 : 중간체 238-1의 합성 1: Synthesis of intermediate 238-1
5,5'-Dibromo-2,2'-bifuran (10.0 g, 0.034 mol), 3,5-Dichlorophenylboronic acid (15.7 g, 0.082 mol), Pd(PPh3)4 (2.4 g, 0.002 mol)에 THF를 넣고 교반하였다. 그 후, H2O에 녹인 NaOH (8.2 g, 0.206 mol)를 첨가하여 65 ℃에서 6시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 238-1>을 10.4 g (수율 71.6%) 수득하였다.THF in 5,5'-Dibromo-2,2'-bifuran (10.0 g, 0.034 mol), 3,5-Dichlorophenylboronic acid (15.7 g, 0.082 mol), Pd(PPh 3 ) 4 (2.4 g, 0.002 mol) was added and stirred. Then, NaOH (8.2 g, 0.206 mol) dissolved in H 2 O was added, and the reaction was stirred at 65° C. for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 10.4 g (yield 71.6%) of <Intermediate 238-1>.
(2) (2) 제조예production example 2 : 화합물 238의 합성 2: Synthesis of compound 238
중간체 238-1 (10.0 g, 0.024 mol), 6-Trifluoromethyl-naphthalen-1-boronic acid (27.2 g, 0.113 mol), K2CO3 (39.1 g, 0.283 mol), 촉매 Pd(OAc)2 (2.7 g, 0.002 mol), 리간드 X-Phos (1.1 g, 0.002 mol), THF 200 mL와 H2O 50 mL, ethanol 50 mL를 넣고 90 ℃에서 6시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 238>을 15.7 g (수율 62.6%) 수득하였다.Intermediate 238-1 (10.0 g, 0.024 mol), 6-Trifluoromethyl-naphthalen-1-boronic acid (27.2 g, 0.113 mol), K 2 CO 3 (39.1 g, 0.283 mol), catalyst Pd(OAc) 2 (2.7 g, 0.002 mol), ligand X-Phos (1.1 g, 0.002 mol), THF 200 mL, H 2 O 50 mL, and ethanol 50 mL were added and reacted by stirring at 90 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 15.7 g (yield 62.6%) of <Compound 238>.
LC/MS: m/z=1062[(M+1)+]LC/MS: m/z=1062 [(M+1) + ]
소자 실시예 (capping layer)Device embodiment (capping layer)
본 발명에 따른 실시예에서, 양극은 25 mm × 25 mm × 0.7 mm의 Ag를 포함하는 ITO 유리 기판을 이용하여, 발광 면적이 2 mm × 2 mm 크기가 되도록 패터닝한 후 세정하였다. 패터닝된 ITO 기판을 진공 챔버에 장착한 후, 1 × 10-6 torr 이상의 공정 압력에서 기판 위에 하기 구조로 유기물과 금속을 증착하였다.In the embodiment according to the present invention, the anode was cleaned using an ITO glass substrate containing 25 mm × 25 mm × 0.7 mm Ag, after patterning so that the light emitting area has a size of 2 mm × 2 mm. After mounting the patterned ITO substrate in a vacuum chamber, organic materials and metals were deposited on the substrate in the following structure at a process pressure of 1 × 10 -6 torr or more.
소자 실시예 1 내지 14Device Examples 1 to 14
본 발명에 따라 구현되는 화합물을 광효율 개선층에 채용하여, 하기와 같은 소자 구조를 갖는 유기발광소자를 제작 후, 본 발명에 따라 구현되는 화합물에 따른 발광 및 구동 특성을 측정하였다.By employing the compound implemented according to the present invention in the light efficiency improving layer, an organic light emitting device having the following device structure was manufactured, and then light emission and driving characteristics according to the compound implemented according to the present invention were measured.
Ag/ITO / 정공주입층 (HAT-CN, 5 nm) / 정공수송층 (α-NPB, 100 nm) / 전자저지층 (TCTA, 10 nm) / 발광층 (20 nm) / 전자수송층 (201:Liq, 30 nm) / LiF (1 nm) / Mg:Ag (15 nm) / 광효율 개선층 (70 nm)Ag/ITO / hole injection layer (HAT-CN, 5 nm) / hole transport layer (α-NPB, 100 nm) / electron blocking layer (TCTA, 10 nm) / light emitting layer (20 nm) / electron transport layer (201: Liq, 30 nm) / LiF (1 nm) / Mg:Ag (15 nm) / Light efficiency improvement layer (70 nm)
유리 기판상에 Ag를 포함하는 ITO 투명 전극 상부에 [HAT-CN]을 5 nm 두께로 성막하여 정공주입층을 형성한 후에 [α-NPB]를 100 nm로 성막하여 정공수송층을 형성하였다. 이후, [TCTA]를 10 nm 두께로 성막하여 전자저지층을 형성하였다. 이후, 호스트 화합물로 [BH1], 도펀트 화합물로 [BD1]을 사용하여 20 nm로 공증착하여 발광층을 형성하였다. 이후, 전자수송층 (하기 [201] 화합물 Liq 50% 도핑)을 30 nm 증착 후, LiF를 1 nm의 두께로 성막하여 전자주입층을 형성하였다. 그 후, Mg:Ag를 1:9의 비율로 15 nm의 두께로 성막하여 캐소드를 형성하였다. 그리고 광효율 개선층(capping layer) 화합물로는 본 발명으로 구현되는 화합물 18, 24, 29, 53, 64, 97, 131, 205, 207, 222, 238, 239, 254, 287를 70 nm의 두께로 성막하여 유기발광소자를 제작하였다.[HAT-CN] was formed on a glass substrate to a thickness of 5 nm on an ITO transparent electrode containing Ag to form a hole injection layer, and then [α-NPB] was formed to a thickness of 100 nm to form a hole transport layer. Then, [TCTA] was formed into a film to a thickness of 10 nm to form an electron blocking layer. Then, using [BH1] as a host compound and [BD1] as a dopant compound, it was co-deposited at 20 nm to form a light emitting layer. Thereafter, after depositing an electron transport layer (50% doping of [201] compound Liq below) at 30 nm, LiF was deposited to a thickness of 1 nm to form an electron injection layer. Thereafter, Mg:Ag was formed into a film to a thickness of 15 nm in a ratio of 1:9 to form a cathode. And as a light efficiency improvement layer (capping layer) compound 18, 24, 29, 53, 64, 97, 131, 205, 207, 222, 238, 239, 254, 287 implemented in the present invention to a thickness of 70 nm By forming a film, an organic light emitting device was manufactured.
소자 비교예 1Device Comparative Example 1
소자 비교예 1을 위한 유기발광소자는 상기 실시예 1 내지 14의 소자구조에서 광효율 개선층을 사용하지 않는 점을 제외하고 동일하게 제작하였다.The organic light emitting device for Device Comparative Example 1 was manufactured in the same manner except that the light efficiency improving layer was not used in the device structures of Examples 1 to 14.
소자 비교예 2Device Comparative Example 2
소자 비교예 2를 위한 유기발광소자는 상기 실시예 1 내지 14의 소자구조에서 광효율 개선층 화합물로 본 발명에 따른 화합물 대신에 하기 Alq3를 사용한 것을 제외하고 동일하게 제작하였다.The organic light emitting device for Device Comparative Example 2 was prepared in the same manner except that Alq 3 was used instead of the compound according to the present invention as the light efficiency improving layer compound in the device structures of Examples 1 to 14.
실험예 1 : 소자 실시예 1 내지 14의 발광 특성Experimental Example 1: Light emitting properties of Device Examples 1 to 14
상기 실시예에 따라 제조된 유기발광소자는 Source meter (Model 237, Keithley)와 휘도계 (PR-650, Photo Research)를 이용하여 구동 전압, 전류 효율 및 색좌표를 측정하였고, 1,000 nit 기준의 결과값은 하기 [표 1]과 같다.The organic light emitting device manufactured according to the above example was measured using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research) to measure driving voltage, current efficiency, and color coordinates, and the result value based on 1,000 nits is shown in [Table 1] below.
상기 [표 1]에 나타낸 결과를 살펴보면, 본 발명에 따른 화합물을 유기발광소자에 구비되는 광효율 개선층에 적용한 경우 종래 광효율 개선층을 구비하지 않은 소자 및 종래 널리 사용된 화합물을 채용한 소자에 (비교예 1 및 2)에 비하여 구동 전압이 감소하고, 전류 효율이 향상되는 것을 확인할 수 있다.Looking at the results shown in [Table 1], when the compound according to the present invention is applied to the light efficiency improving layer provided in the organic light emitting device, it is applied to the device without the conventional light efficiency improving layer and the device employing the conventionally widely used compound ( It can be seen that the driving voltage is reduced and the current efficiency is improved compared to Comparative Examples 1 and 2).
[HAT-CN] [α-NPB] [BH1] [BD1] [201][HAT-CN] [α-NPB] [BH1] [BD1] [201]
[TCTA][TCTA]
Claims (7)
[화학식 Ⅰ]
상기 [화학식 Ⅰ]에서,
X는 O 또는 S이고,
R은 각각 독립적으로 수소, 중수소, 할로겐기, 시아노기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기, 치환 또는 비치환된 탄소수 1 내기 20의 알콕시기, 치환 또는 비치환된 탄소수 1 내지 20의 할로겐화된 알킬기, 치환 또는 비치환된 탄소수 1 내지 20의 중수소화된 알킬기, 치환 또는 비치환된 탄소수 1 내지 20의 할로겐화된 알콕시기, 치환 또는 비치환된 탄소수 1 내지 20의 중수소화된 알콕시기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬실릴기 및 치환 또는 비치환된 탄소수 6 내지 30의 아릴실릴기 중에서 선택되며,
n은 0 내지 2의 정수이며, 상기 n이 2인 경우 R이 복수 개인 경우 서로 동일하거나 상이하고,
m은 1 내지 3의 정수이며, 상기 m이 2이상인 경우 복수 개의 [ ] 내 구조체는 서로 동일하거나 상이하고,
R1 내지 R4는 서로 동일하거나 상이하고, 각각 독립적으로 중수소, 시아노기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 치환 또는 비치환된 탄소수 1 내지 20의 할로겐화된 알킬기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬실릴기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴실릴기, 치환 또는 비치환된 나프틸, 치환 또는 비치환된 플루오렌, 치환 또는 비치환된 벤조옥사졸, 치환 또는 비치환된 벤조티아졸, 치환 또는 비치환된 다이벤조퓨란 및 치환 또는 비치환된 다이벤조티오펜 중에서 선택된다.An organic light emitting compound represented by the following [Formula I]:
[Formula Ⅰ]
In the [Formula I],
X is O or S;
R is each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 Alkoxy group, substituted or unsubstituted halogenated alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted deuterated alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted halogenated alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted A substituted or unsubstituted C1 to C20 deuterated alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 It is selected from an alkylsilyl group and a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms,
n is an integer from 0 to 2, and when n is 2, when R is a plurality, they are the same or different from each other,
m is an integer of 1 to 3, and when m is 2 or more, a plurality of structures in [ ] are the same or different from each other,
R 1 to R 4 are the same as or different from each other, and each independently represents a deuterium, a cyano group, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 1 to C 20 halogenated alkyl group, a substituted or unsubstituted an alkylsilyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorene, a substituted or unsubstituted benzoxazole, a substituted or unsubstituted benzothiazole, substituted or unsubstituted dibenzofuran and substituted or unsubstituted dibenzothiophene.
상기 R 및 R1 내지 R4의 정의에서, '치환 또는 비치환된'이라 함은 중수소, 할로겐기, 시아노기, 니트로기, 히드록시기, 실릴기, 알킬기, 시클로알킬기, 알콕시기, 알케닐기, 아릴기 및 헤테로아릴기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되거나, 상기 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미하는 것을 특징으로 하는 유기발광 화합물.According to claim 1,
In the definitions of R and R 1 to R 4 , 'substituted or unsubstituted' means deuterium, a halogen group, a cyano group, a nitro group, a hydroxy group, a silyl group, an alkyl group, a cycloalkyl group, an alkoxy group, an alkenyl group, an aryl group An organic light-emitting compound, characterized in that it is substituted with one or two or more substituents selected from the group consisting of a group and a heteroaryl group, or substituted with a substituent to which two or more of the substituents are connected, or does not have any substituents.
상기 [화학식 Ⅰ]은 하기 [화합물 1] 내지 [화합물 293] 중에서 선택되는 것을 특징으로 하는 유기발광 화합물:
The [Formula I] is an organic light emitting compound, characterized in that selected from the following [Compound 1] to [Compound 293]:
상기 유기층 중 1 층 이상은 제1항에 따른 [화학식 Ⅰ]의 유기발광 화합물을 포함하는 것인 유기발광소자.An organic light emitting device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode,
At least one of the organic layers is an organic light emitting device comprising the organic light emitting compound of [Formula I] according to claim 1.
상기 유기층은 정공 주입층, 정공 수송층, 정공 주입과 정공 수송 기능을 동시에 하는 층, 전자 수송층, 전자 주입층, 전자 수송과 전자 주입 기능을 동시에 하는 층, 전자 저지층, 정공 저지층 및 발광층 중에서 선택되는 1층 이상을 포함하고,
상기 층들 중 1층 이상이 상기 [화학식 Ⅰ]로 표시되는 유기발광 화합물을 포함하는 것을 특징으로 하는 유기발광소자.5. The method of claim 4,
The organic layer is selected from a hole injection layer, a hole transport layer, a layer that performs both hole injection and hole transport functions, an electron transport layer, an electron injection layer, a layer that performs both electron transport and electron injection functions, an electron blocking layer, a hole blocking layer and a light emitting layer including one or more floors that become
At least one of the layers comprises an organic light emitting compound represented by the [Formula I].
상기 제1 전극과 제2 전극의 상부 또는 하부 중에서 상기 유기층과 반대되는 적어도 일측에 형성되는 광효율 개선층 (Capping layer)을 더 포함하고,
상기 광효율 개선층은 상기 [화학식 Ⅰ]로 표시되는 유기발광 화합물을 포함하는 것을 특징으로 하는 유기발광소자.6. The method of claim 5,
Further comprising a light efficiency improvement layer (Capping layer) formed on at least one side opposite to the organic layer among the upper or lower portions of the first electrode and the second electrode,
The light efficiency improving layer is an organic light emitting device, characterized in that it comprises an organic light emitting compound represented by the [Formula I].
상기 광효율 개선층은 상기 제1 전극의 하부 또는 상기 제2 전극의 상부 중 적어도 하나에 형성되는 것을 특징으로 하는 유기발광소자.7. The method of claim 6,
The light efficiency improving layer is an organic light emitting device, characterized in that formed on at least one of a lower portion of the first electrode or an upper portion of the second electrode.
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