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KR-20260068048-A - ORGANIC ELECTROLUMINESCENCE DEVICE AND AMINE COMPOUND FOR ORGANIC ELECTROLUMINESCENCE DEVICE

KR20260068048AKR 20260068048 AKR20260068048 AKR 20260068048AKR-20260068048-A

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
  • 한상현
  • 정은재
  • 박한규
  • 김민지
  • 김동준

Assignees

  • 삼성디스플레이 주식회사

Dates

Publication Date
20260513
Application Date
20260430

Claims (14)

  1. First electrode; A hole transport region disposed on the first electrode; A light-emitting layer disposed on the above-mentioned hole transport region; Electron transport region disposed on the light-emitting layer; and A second electrode disposed on the electron transport region; comprising, The hole transport region 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, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, 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. 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.
  2. In paragraph 1, 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 above hole transport layer is an organic electroluminescent device comprising an amine compound represented by the above chemical formula 3.
  3. In paragraph 1, 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, wherein the organic layer comprises an amine compound represented by Chemical Formula 3.
  4. In paragraph 1, 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.
  5. In paragraph 1, 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.
  6. In paragraph 1, 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.
  7. In paragraph 1, 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] .
  8. First electrode; A second electrode facing the first electrode; and A plurality of organic layers disposed between the first electrode and the second electrode, each including a light-emitting layer, and The organic layer adjacent to the light-emitting layer among the plurality of 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.
  9. In paragraph 8, The above-mentioned light-emitting layer is an organic electroluminescent device comprising a host and a dopant.
  10. In Paragraph 9, The above host is an organic electroluminescent device comprising a compound represented by the following chemical formula E-1: [Chemical Formula E-1] In the above chemical formula E-1, R 31 to R 40 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or form a ring by bonding to an adjacent group, Organic electroluminescent devices in which c and d are each independently integers from 0 to 5.
  11. In paragraph 8, 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.
  12. In paragraph 8, 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.
  13. In paragraph 8, 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.
  14. In paragraph 8, 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] .

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