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KR-20260062793-A - LIGHT EMITTING DEVICE, FUSED POLYCYCLIC COMPOUND FOR THE SAME, AND ELECTRONIC DEVICE INCLUDING THE SAME

KR20260062793AKR 20260062793 AKR20260062793 AKR 20260062793AKR-20260062793-A

Abstract

A light-emitting element of one embodiment includes a first electrode, a second electrode disposed on the first electrode, and a light-emitting layer disposed between the first electrode and the second electrode and comprising a first compound represented by the following chemical formula 1. [Chemical Formula 1]

Inventors

  • 호시, 케이고
  • 김정은
  • 야마모토, 마코토

Assignees

  • 삼성디스플레이 주식회사

Dates

Publication Date
20260507
Application Date
20250430
Priority Date
20241024

Claims (20)

  1. First electrode; A second electrode disposed on the first electrode; and A light-emitting element comprising a light-emitting layer disposed between the first electrode and the second electrode, and comprising a first compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X 1 to X 3 are each independently O, S, or NAr 1 , and Ar 1 is 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, and R1 to R15 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, 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. When R 13 is a diphenylamine group or a carbazole group, cases where R 10 is a hydrogen atom or includes a diphenylamine group are excluded, and The first compound represented by the above chemical formula 1 includes a structure in which at least one hydrogen atom is substituted with a deuterium atom.
  2. In paragraph 1, The above-mentioned light-emitting layer includes a host and a dopant, and The above dopant is a light-emitting element comprising a first compound represented by the above chemical formula 1.
  3. In paragraph 1, The first compound represented by the above chemical formula 1 is a light-emitting element represented by any one of the following chemical formulas 2-1 to 2-4: [Chemical Formula 2-1] [Chemical Formula 2-2] [Chemical Formula 2-3] [Chemical Formula 2-4] In the above chemical formulas 2-1 to 2-4, X 2a and X 3a are each independently O or S, and R 21 to R 24 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, 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. n1 to n4 are each independently integers from 0 to 5, and X 1 , and R 1 to R 15 are the same as defined in Chemical Formula 1 above.
  4. In paragraph 1, The first compound represented by the above chemical formula 1 is a light-emitting element represented by any one of the following chemical formulas 3-1 to 3-4: [Chemical Formula 3-1] [Chemical Formula 3-2] [Chemical Formula 3-3] [Chemical Formula 3-4] In the above chemical formulas 3-1 to 3-4, R 21 to R 24 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, 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. n1 to n4 are each independently integers from 0 to 5, and In the above chemical formula 3-2, If R 13 is a diphenylamine group or a carbazole group, R 10 is an unsubstituted alkyl group having 1 to 20 carbon atoms, or an unsubstituted ring-forming aryl group having 6 to 20 carbon atoms, and X 1 , and R 1 to R 15 are the same as defined in Chemical Formula 1 above.
  5. In paragraph 1, The first compound represented by the above chemical formula 1 is a light-emitting element represented by any one of the following chemical formulas 4-1 to 4-4: [Chemical Formula 4-1] [Chemical Formula 4-2] [Chemical Formula 4-3] [Chemical Formula 4-4] In the above chemical formulas 4-1 to 4-4, X 1a and X 2a are each independently O, or S, and R 31 to R 34 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, 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. n11 to n14 are each independently integers from 0 to 5, and X3 , and R1 to R15 are the same as defined in Chemical Formula 1 above.
  6. In paragraph 1, The first compound represented by the above chemical formula 1 is a light-emitting element represented by the following chemical formula 5: [Chemical Formula 5] In the above chemical formula 5, At least one of X 1b , X 2b , and X 3b is represented by the following formula 6-1 or formula 6-2, and the remainder are each independently O, S, or NAr 2 , and Ar 2 is 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, and R1 to R15 are the same as defined in Chemical Formula 1 above: [Chemical Formula 6-1] [Chemical Formula 6-2] In the above chemical formulas 6-1 and 6-2, R 41 to R 45 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, 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. n21, n23, and n25 are each independently integers from 0 to 5, and n22 is an integer between 0 and 4 inclusive, and n24 is an integer between 0 and 3 inclusive, and is the position connected to the above chemical formula 5.
  7. In paragraph 1, The above X 1 to X 3 are each independently O or NAr 3 , and Ar 3 is a light-emitting element in which the aryl group is substituted or unsubstituted and has 6 to 30 carbon atoms.
  8. In paragraph 3, In the above chemical formula 1, Where R 13 is a diphenylamine group or a carbazole group, R 10 is 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 heteroaryl group having 2 to 30 carbon atoms, and A light-emitting element in which, when R 10 is substituted, the substituent is a deuterium atom, a cyano group, an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted aryl group having 6 to 15 carbon atoms, or an unsubstituted heteroaryl group having 2 to 15 carbon atoms.
  9. In paragraph 1, The light-emitting layer comprises a light-emitting element further including at least one of a second compound represented by the following chemical formula HT-1, a third compound represented by the following chemical formula ET-1, and a fourth compound represented by the following chemical formula D-1: [Chemical Formula HT-1] In the above chemical formula HT-1, M 1 to M 8 are each independently N or CR 51 , and L1 is a direct linkage, substituted or unsubstituted cyclic arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic arylene group having 2 to 30 carbon atoms, and Y a is a direct bond, CR 52 R 53 , or SiR 54 R 55 , and Ar a is 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, and R 51 to R 55 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 60 carbon atoms, or they form a ring by bonding to adjacent groups: [Chemical Formula ET-1] In the above chemical formula ET-1, At least one of Z a to Z c is N and the rest are CR 56 , and R 56 is a hydrogen atom, a deuterium 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 b1 to b3 are each independently integers from 0 to 10, and Ar b to Ar d are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 2 to 30 carbon atoms. L2 to L4 are each independently a directly bonded, substituted, or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted arylene group having 2 to 30 carbon atoms: [Chemical Formula D-1] In the above chemical formula D-1, Q1 to Q4 are each independently C or N, and C1 to C4 are each independently a substituted or unsubstituted ring-forming hydrocarbon ring having 5 to 30 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic ring having 2 to 30 carbon atoms. X 11 to X 14 are each independently directly combined or And, L 11 to L 13 are each independently directly combined, , , , , a substituted or unsubstituted divalent alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group having 2 to 30 carbon atoms, and b11 to b13 are each independently 0 or 1, and R 61 to R 66 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 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. d1 to d4 are each independently integers from 0 to 4.
  10. In paragraph 1, A light-emitting device comprising at least one of the compounds of the following compound group 1, wherein the first compound represented by the above chemical formula 1 is a first compound: [Compound Group 1] .
  11. Base layer; A circuit layer disposed on the above base layer; and It includes a display element layer disposed on the above circuit layer and including a light-emitting element, and The above-described light-emitting element is an electronic device comprising a first electrode, a second electrode disposed on the first electrode, and a light-emitting layer disposed between the first electrode and the second electrode and comprising a first compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X 1 to X 3 are each independently O, S, or NAr 1 , and Ar 1 is 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, and R1 to R15 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, 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. When R 13 is a diphenylamine group or a carbazole group, cases where R 10 is a hydrogen atom or includes a diphenylamine group are excluded, and The first compound represented by the above chemical formula 1 includes a structure in which at least one hydrogen atom is substituted with a deuterium atom.
  12. In Paragraph 11, The light-emitting element further includes a capping layer disposed on the second electrode, and An electronic device in which the refractive index of the capping layer is 1.6 or higher for light in a wavelength range of 550 nm or more and 660 nm or less.
  13. In Paragraph 11, It further includes a light control layer disposed on the above-mentioned display element layer and comprising quantum dots, and The light-emitting element emits a first color light, and The above light control layer A first light control unit comprising a first quantum dot that converts a first color light into a second color light in a longer wavelength region than the first color light; A second light control unit comprising a second quantum dot that converts the first color light into a third color light in a longer wavelength region than the first color light and the second color light; and An electronic device comprising: a third light control unit that transmits the first colored light.
  14. In Paragraph 13, It further includes a color filter layer disposed on the light control layer above, and The above color filter layer A first filter that transmits the above second colored light; A second filter that transmits the above-mentioned third colored light; and An electronic device comprising: a third filter that transmits the first colored light.
  15. In Paragraph 11, The above electronic device is an electronic device selected from large display devices such as televisions, monitors, and external billboards, personal computers, laptop computers, personal digital terminals, vehicle display devices, game consoles, portable electronic devices, and small and medium-sized display devices such as cameras.
  16. Condensed polycyclic compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X 1 to X 3 are each independently O, S, or NAr 1 , and Ar 1 is 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, and R1 to R15 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, 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. When R 13 is a diphenylamine group or a carbazole group, cases where R 10 is a hydrogen atom or includes a diphenylamine group are excluded, and The condensed polycyclic compound represented by the above chemical formula 1 includes a structure in which at least one hydrogen atom is substituted with a deuterium atom.
  17. In Paragraph 16, The condensed polycyclic compound represented by the above chemical formula 1 is a condensed polycyclic compound represented by any one of the following chemical formulas 2-1 to 2-4: [Chemical Formula 2-1] [Chemical Formula 2-2] [Chemical Formula 2-3] [Chemical Formula 2-4] In the above chemical formulas 2-1 to 2-4, X 2a and X 3a are each independently O or S, and R 21 to R 24 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, 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. n1 to n4 are each independently integers from 0 to 5, and X 1 , and R 1 to R 15 are the same as defined in Chemical Formula 1 above.
  18. In Paragraph 16, The condensed polycyclic compound represented by the above Chemical Formula 1 is a condensed polycyclic compound represented by any one of the following Chemical Formulas 3-1 to 3-4: [Chemical Formula 3-1] [Chemical Formula 3-2] [Chemical Formula 3-3] [Chemical Formula 3-4] In the above chemical formulas 3-1 to 3-4, R 21 to R 24 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, 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. n1 to n4 are each independently integers from 0 to 5, and In the above chemical formula 3-2, If R 13 is a diphenylamine group or a carbazole group, R 10 is an unsubstituted alkyl group having 1 to 20 carbon atoms, or an unsubstituted ring-forming aryl group having 6 to 20 carbon atoms, and X 1 , and R 1 to R 15 are the same as defined in Chemical Formula 1 above.
  19. In Paragraph 16, The condensed polycyclic compound represented by the above chemical formula 1 is a condensed polycyclic compound represented by any one of the following chemical formulas 4-1 to 4-4: [Chemical Formula 4-1] [Chemical Formula 4-2] [Chemical Formula 4-3] [Chemical Formula 4-4] In the above chemical formulas 4-1 to 4-4, X 1a and X 2a are each independently O, or S, and R 31 to R 34 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, 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. n11 to n14 are each independently integers from 0 to 5, and X3 , and R1 to R15 are the same as defined in Chemical Formula 1 above.
  20. In Paragraph 16, A condensed polycyclic compound represented by the above chemical formula 1 is a condensed polycyclic compound comprising at least one of the compounds of the following compound group 1: [Compound Group 1] .

Description

Light-emitting device, condensed polycyclic compound for the same, and electronic device including the same The present invention relates to a light-emitting element, a condensed polycyclic compound used in the light-emitting element, and an electronic device comprising the light-emitting element. 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 particular, recently, to realize high-efficiency organic electroluminescent devices, technologies for phosphorescent emission using the energy of the triplet state or fluorescence emission using the phenomenon of triplet-triplet annihilation (TTA), in which a singlet exciton is generated by the collision of a triplet exciton, are being developed, and the development of thermally activated delayed fluorescence (TADF) materials using the delayed fluorescence phenomenon is underway. 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 a light-emitting element according to one embodiment of the present invention. FIG. 4 is a cross-sectional view schematically showing a light-emitting element according to one embodiment of the present invention. FIG. 5 is a cross-sectional view schematically showing a light-emitting element according to one embodiment of the present invention. FIG. 6 is a cross-sectional view schematically showing a light-emitting element 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 of the present invention. FIG. 9 is a cross-sectional view showing a display device according to one embodiment of the present invention. FIG. 10 is a cross-sectional view showing a display device according to one embodiment of the present invention. FIG. 11 is a drawing showing a vehicle with a display device installed according to one embodiment. 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 describing each drawing, similar reference numerals have been used for similar components. In the attached drawings, the dimensions of the structures are depicted enlarged from their actual size for clarity of the invention. 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 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. In this application, terms such as "comprising" or "having" are intended to specify 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 application, when a part such as a layer, film, region, or plate is described as being "on" or "upper" to another part, this includes not only cases where it is "immediately above" the other part, but also cases where there is another part in between. Conversely, when a part such as a layer, film, region, or plate is described as being "under" or "lower" to another part, this includes not only cases where it is "immediately below" the other part, but also cases where there is another part in between. Furthermore, in this application, being "placed on" may include cases where it is placed not only on the upper part but also on the lower part. In this specification,