KR-102961670-B1 - ORGANIC ELECTROLUMINESCENCE DEVICE AND AMINE COMPOUND FOR ORGANIC ELECTROLUMINESCENCE DEVICE

KR102961670B1KR 102961670 B1KR102961670 B1KR 102961670B1KR-102961670-B1

Abstract

An organic electroluminescent device of one embodiment comprises a first electrode and a second electrode facing each other, and a plurality of organic layers disposed between the first electrode and the second electrode, and at least one of the organic layers comprises an amine compound represented by the following chemical formula 1, which can exhibit improved luminescence efficiency. [Chemical Formula 1]

Inventors

조소희
김동준
김민지
박한규
정은재
한상현

Assignees

삼성디스플레이 주식회사

Dates

Publication Date: 20260511
Application Date: 20200821

Claims (20)

First electrode; A second electrode facing the first electrode; and It includes a plurality of organic layers disposed between the first electrode and the second electrode, and At least one of the above organic layers comprises an amine compound, and The above amine compound is a monoamine compound, and The above amine compound comprises an amine group, a spirofluorenedine group substituted on the amine group, and Ar1 and Ar2 substituted on the amine group, and The above amine group is connected to one of the fluorene group portions included in the above spirofluoreneindine group, a benzene ring, and The above Ar 1 is a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, and The above Ar 2 is an organic electroluminescent device in which the above Ar 2 is a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophen group, or an unsubstituted 9-phenylcarbazole group.
In paragraph 1, An organic electroluminescent device in which the above-mentioned spirofluoreneindine group is bonded to the above-mentioned amine group through a linker or directly bonded.
In paragraph 1, The above organic layers are A hole transport region disposed on the first electrode; A light-emitting layer disposed on the above-mentioned hole transport region; and It includes an electron transport region disposed on the light-emitting layer, and The hole transport region above is an organic electroluminescent device comprising the amine compound above.
In paragraph 3, The above hole transport region is A hole injection layer disposed on the first electrode; and It includes a hole transport layer disposed on the hole injection layer above, and The hole transport layer above is an organic electroluminescent device comprising the amine compound.
In paragraph 3, The above hole transport region includes a plurality of organic layers, and An organic electroluminescent device comprising an organic layer adjacent to the light-emitting layer among the plurality of organic layers, the organic layer comprising the amine compound.
First electrode; A second electrode facing the first electrode; and It includes a plurality of organic layers disposed between the first electrode and the second electrode, and At least one organic layer among the above organic layers comprises an amine compound represented by the following chemical formula 3, and The above amine compound is an organic electroluminescent device that is a monoamine compound: [Chemical Formula 3] In the above chemical formula 3, X is O, S, or NAr 3 , and Ar 1 is a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, and Ar3 is a hydrogen atom, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, and L1 and L2 are each independently a directly linked, substituted or unsubstituted cyclic arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroarylene group having 2 to 30 carbon atoms, and R1 to R5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and R 11 to R 14 are each independently a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and n 1, n 2 , and n 4 are each independently integers between 0 and 4 inclusive, and n 3 and n 5 are each independently integers greater than or equal to 0 and less than or equal to 3.
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In paragraph 6, An amine compound represented by the above chemical formula 3 is an organic electroluminescent device represented by any one of the following chemical formulas 4-1 to 4-3: [Chemical Formula 4-1] [Chemical Formula 4-2] [Chemical Formula 4-3] In the above chemical formulas 4-1 to 4-3, Ar 1 , X, L 1 , L 2 , R 1 , R 2 , R 3 , R 4 , R 5 , R 11 , R 12 , R 13 , R 14 , n 1 , n 2 , n 3 , n 4 , and n 5 are the same as defined in Chemical Formula 3 above.
In paragraph 6, An amine compound represented by the above chemical formula 3 is an organic electroluminescent device represented by any one of the following chemical formulas 5-1 to 5-3: [Chemical Formula 5-1] [Chemical Formula 5-2] [Chemical Formula 5-3] In the above chemical formulas 5-1 to 5-3, R6 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 60 carbon atoms, and n 6 is an integer between 0 and 4 inclusive, and Ar 1 , X, L 1 , R 1 , R 2 , R 3 , R 4 , R 5 , R 11 , R 12 , R 13 , R 14 , n 1 , n 2 , n 3 , n 4 , and n 5 are the same as defined in Chemical Formula 3 above.
In paragraph 6, An organic electroluminescent device in which the above Ar 1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group.
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In paragraph 6, An organic electroluminescent device wherein the above amine compound is at least one selected from the compounds listed in the compound group 1 below: [Compound Group 1] .
An amine compound represented by the following chemical formula 3 and being a monoamine compound: [Chemical Formula 3] In the above chemical formula 3, X is O, S, or NAr 3 , and Ar 1 is a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, and Ar3 is a hydrogen atom, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, and L1 and L2 are each independently a directly linked, substituted or unsubstituted cyclic arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroarylene group having 2 to 30 carbon atoms, and R1 to R5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and R 11 to R 14 are each independently a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted cyclic alkyl group having 1 to 20 carbon atoms, and n 1, n 2 , and n 4 are each independently integers between 0 and 4 inclusive, and n 3 and n 5 are each independently integers greater than or equal to 0 and less than or equal to 3.
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In paragraph 15, The amine compound represented by the above chemical formula 3 is an amine compound represented by any one of the following chemical formulas 4-1 to 4-3: [Chemical Formula 4-1] [Chemical Formula 4-2] [Chemical Formula 4-3] In the above chemical formulas 4-1 to 4-3, Ar 1 , X, L 1 , L 2 , R 1 , R 2 , R 3 , R 4 , R 5 , R 11 , R 12 , R 13 , R 14 , n 1 , n 2 , n 3 , n 4 , and n 5 are the same as defined in Chemical Formula 3 above.
In paragraph 15, The amine compound represented by the above chemical formula 3 is an amine compound represented by any one of the following chemical formulas 5-1 to 5-3: [Chemical Formula 5-1] [Chemical Formula 5-2] [Chemical Formula 5-3] In the above chemical formulas 5-1 to 5-3, R6 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 60 carbon atoms, and n 6 is an integer between 0 and 4 inclusive, and Ar 1 , X, L 1 , R 1 , R 2 , R 3 , R 4 , R 5 , R 11 , R 12 , R 13 , R 14 , n 1 , n 2 , n 3 , n 4 , and n 5 are the same as defined in Chemical Formula 3 above.
In paragraph 15, The above amine compound is an amine compound comprising at least one of the compounds of the following compound group 1: [Compound Group 1] .

Description

Organic Electroluminescent Device and Amine Compound for Organic Electroluminescent Device The present invention relates to an organic electroluminescent device and an amine compound used therein, and more specifically, to an amine compound used as a light-emitting material and an organic electroluminescent device containing the same. Recently, there has been active development of organic electroluminescence displays as image display devices. Unlike liquid crystal displays, organic electroluminescence displays are so-called self-emissive display devices that realize a display by causing a light-emitting material containing an organic compound in the light-emitting layer to emit light by recombining holes and electrons injected from a first electrode and a second electrode in the light-emitting layer. In applying organic light-emitting diodes to display devices, there is a demand for lower driving voltage, higher luminous efficiency, and longer lifespan of the devices, and there is a continuous demand for the development of materials for organic light-emitting diodes that can stably realize these requirements. In addition, development of hole transport layer materials is underway to realize high-efficiency organic electroluminescent devices. FIG. 1 is a plan view of a display device according to one embodiment of the present invention. FIG. 2 is a cross-sectional view of a display device according to one embodiment of the present invention. FIG. 3 is a cross-sectional view schematically showing an organic electroluminescent device according to one embodiment of the present invention. FIG. 4 is a cross-sectional view schematically showing an organic electroluminescent device according to one embodiment of the present invention. FIG. 5 is a cross-sectional view schematically showing an organic electroluminescent device according to one embodiment of the present invention. FIG. 6 is a cross-sectional view schematically showing an organic electroluminescent device according to one embodiment of the present invention. FIGS. 7 and FIGS. 8 are cross-sectional views of a display device according to one embodiment, respectively. The present invention is capable of various modifications and may take various forms, and specific embodiments are illustrated in the drawings and described in detail in the text. However, this is not intended to limit the invention to the specific disclosed forms, and it should be understood that the invention includes all modifications, equivalents, and substitutions that fall within the spirit and scope of the invention. In this specification, where a component (or region, layer, part, etc.) is described as being "on," "connected," or "combined" with another component, it means that it may be directly placed/connected/combined with the other component, or that a third component may be placed between them. Identical reference numerals denote identical components. Additionally, in the drawings, the thicknesses, proportions, and dimensions of the components are exaggerated for the effective illustration of the technical content. "And/or" includes all one or more combinations that the associated configurations can define. Terms such as "first," "second," etc., may be used to describe various components, but said components should not be limited by said terms. These terms are used solely for the purpose of distinguishing one component from another. For example, without departing from the scope of the present invention, the first component may be named the second component, and similarly, the second component may be named the first component. A singular expression includes a plural expression unless the context clearly indicates otherwise. Additionally, terms such as "below," "lower side," "above," and "upper side" are used to describe the relationships between the components depicted in the drawings. These terms are relative concepts and are described based on the directions indicated in the drawings. Unless otherwise defined, all terms used herein (including technical and scientific terms) have the same meaning as generally understood by those skilled in the art to which the present invention pertains. Additionally, terms such as those defined in commonly used dictionaries should be interpreted as having a meaning consistent with their meaning in the context of the relevant technology, and are explicitly defined herein unless interpreted in an ideal or overly formal sense. Terms such as "include" or "have" are intended to indicate the existence of the features, numbers, steps, actions, components, parts, or combinations thereof described in the specification, and should be understood as not precluding the existence or addition of one or more other features, numbers, steps, actions, components, parts, or combinations thereof. In this specification, "substituted or unsubstituted" may mean substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium a