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KR-102963055-B1 - ORGANIC LIGHT EMITTING DEVICE

KR102963055B1KR 102963055 B1KR102963055 B1KR 102963055B1KR-102963055-B1

Abstract

The present invention relates to an organic light-emitting diode and an organic light-emitting device comprising at least one light-emitting material layer comprising a host in which an anthracene core is substituted with deuterium and a main dopant, at least one electron blocking layer comprising an amine-based compound substituted with an aryl group, and at least one hole blocking layer comprising an azine-based or benzimidazole-based compound as needed. By applying the organic compound according to the present invention to a light-emitting device, the light-emitting efficiency of the device can be improved and the light-emitting lifespan can be significantly enhanced.

Inventors

  • 윤승희
  • 김상범
  • 송인범
  • 카즈시 시렌
  • 야수유키 사사다

Assignees

  • 엘지디스플레이 주식회사
  • 에스케이머티리얼즈제이엔씨 주식회사

Dates

Publication Date
20260511
Application Date
20210517
Priority Date
20200529

Claims (19)

  1. Substrate; and A light-emitting layer comprising a first electrode, a second electrode facing the first electrode, at least one light-emitting material layer located between the first electrode and the second electrode, and at least one electron blocking layer located between the first electrode and the at least one light-emitting material layer, and an organic light-emitting diode located on the substrate. The above at least one light-emitting material layer comprises a first host which is an anthracene-based compound and a first dopant which is a boron-based compound, and The anthracene core of the first host is substituted with deuterium, and the first dopant comprises any one compound having the structure of Chemical Formula 4 below, An organic light-emitting device comprising at least one electron blocking layer having an amine-based compound having the structure of Chemical Formula 5 below. [Chemical Formula 4] [Chemical Formula 5] In Chemical Formula 5, R61 , R62 , and R64 are each independently a single-ring aryl group or a polycyclic aryl group, R63 is a single-ring arylene or a polycyclic arylene, and at least one of R61 to R64 is polycyclic.
  2. In Article 1, The above-mentioned first host is an organic light-emitting device comprising an anthracene-based compound having the structure of Chemical Formula 1 below. [Chemical Formula 1] In Chemical Formula 1, R1 and R2 are each independently a C6 - C30 aryl or a C5 - C30 heteroaryl, L1 is a C6 - C30 arylene, a is an integer of 0 or 1, and b is an integer of 1 to 8.
  3. In Paragraph 2, The above-mentioned first host is an organic light-emitting device comprising any one of the compounds having the structure of Chemical Formula 2 below. [Chemical Formula 2]
  4. delete
  5. In Article 1, An organic light-emitting device comprising any one of the compounds having the structure of Chemical Formula 6 below, wherein the above amine-based compound. [Chemical Formula 6]
  6. In Article 1, The above-described light-emitting layer further comprises at least one hole-blocking layer located between the at least one light-emitting material layer and the second electrode, forming an organic light-emitting device.
  7. In Paragraph 6, An organic light-emitting device comprising at least one hole-blocking layer having an azine-based compound having the structure of Chemical Formula 7 below or a benzimidazole-based compound having the structure of Chemical Formula 9 below. [Chemical Formula 7] In Chemical Formula 7, Y1 to Y5 are each independently CR71 or nitrogen (N), of which 1 to 3 are nitrogen, and R71 is a C6 - C30 aryl; L3 is a C6 - C30 arylene group; R 72 is a C 6 -C 30 aryl or a C 5 -C 30 heteroaryl, and the C 6 -C 30 aryl may be unsubstituted, substituted with another C 6 -C 30 aryl or C 5 -C 30 heteroaryl, or may form a spiro structure with a C 10 -C 30 condensed aryl ring or a C 10 -C 30 condensed heteroaryl ring, and the other C 6 -C 30 aryl may be unsubstituted, substituted with another C 6 -C 30 aryl or another C 5 -C 30 heteroaryl, or may form a spiro structure with a C 10 -C 30 condensed aryl ring; R 73 is hydrogen or adjacent groups combine to form a condensed aromatic ring; f is 0 or 1, g is 1 or 2, and h is an integer from 0 to 4. [Chemical Formula 9] In chemical formula 9, Ar is a C10 - C30 arylene group; R81 is a C6 - C30 aryl or C5 - C30 heteroarylaryl, and the C6 - C30 aryl and C5 - C30 heteroaryl may each be unsubstituted or substituted with a C1 - C10 alkyl; R82 and R83 are each independently hydrogen, a C1 - C10 alkyl, or a C6 - C30 aryl.
  8. In Article 7, The above-mentioned azine compound comprises any one of the azine compounds having the structure of Chemical Formula 8 below, and The above benzimidazole-based compound is an organic light-emitting device comprising any one of the compounds having the structure of Chemical Formula 10 below. [Chemical Formula 8] [Chemical Formula 10]
  9. In Article 1, The light-emitting layer further comprises a first light-emitting unit located between the first electrode and the second electrode and including a first light-emitting material layer and a first electron blocking layer located between the first electrode and the first light-emitting material layer, a second light-emitting unit located between the first light-emitting unit and the second electrode and including a second light-emitting material layer, and a first charge-generating layer located between the first light-emitting unit and the second light-emitting unit. An organic light-emitting device comprising at least one of the first light-emitting material layer and the second light-emitting material layer, the first host and the first dopant.
  10. In Article 9, The above second light-emitting unit further comprises a second electron blocking layer located between the first charge generating layer and the second light-emitting material layer, and at least one of the first electron blocking layer and the second electron blocking layer comprises an amine-based compound having the structure of Formula 5.
  11. In Article 10, An organic light-emitting device comprising at least one hole blocking layer among a first hole blocking layer located between the first light-emitting material layer and the first charge-generating layer and a second hole blocking layer located between the second light-emitting material layer and the second electrode.
  12. In Paragraph 11, An organic light-emitting device comprising at least one hole-blocking layer having an azine-based compound having the structure of Chemical Formula 7 below or a benzimidazole-based compound having the structure of Chemical Formula 9 below. [Chemical Formula 7] In Chemical Formula 7, Y1 to Y5 are each independently CR71 or nitrogen (N), of which 1 to 3 are nitrogen, and R71 is a C6 - C30 aryl; L3 is a C6 - C30 arylene group; R 72 is a C 6 -C 30 aryl or a C 5 -C 30 heteroaryl, and the C 6 -C 30 aryl may be unsubstituted, substituted with another C 6 -C 30 aryl or C 5 -C 30 heteroaryl, or may form a spiro structure with a C 10 -C 30 condensed aryl ring or a C 10 -C 30 condensed heteroaryl ring, and the other C 6 -C 30 aryl may be unsubstituted, substituted with another C 6 -C 30 aryl or another C 5 -C 30 heteroaryl, or may form a spiro structure with a C 10 -C 30 condensed aryl ring; R 73 is hydrogen or adjacent groups combine to form a condensed aromatic ring; f is 0 or 1, g is 1 or 2, and h is an integer from 0 to 4. [Chemical Formula 9] In chemical formula 9, Ar is a C10 - C30 arylene group; R81 is a C6 - C30 aryl or C5 - C30 heteroarylaryl, and the C6 - C30 aryl and C5 - C30 heteroaryl may each be unsubstituted or substituted with a C1 - C10 alkyl; R82 and R83 are each independently hydrogen, a C1 - C10 alkyl, or a C6 - C30 aryl.
  13. In Article 9, The above second light-emitting material layer is an organic light-emitting device that emits yellow-green or red-green light.
  14. In Paragraph 13, The light-emitting layer further comprises a third light-emitting unit located between the second light-emitting unit and the second electrode and including a third light-emitting material layer, and a second charge-generating layer located between the second light-emitting unit and the third light-emitting unit. An organic light-emitting device comprising at least one of the first light-emitting material layer and the third light-emitting material layer, the first host and the first dopant.
  15. In Paragraph 14, The above third light-emitting unit further comprises a third electron blocking layer located between the second charge generating layer and the third light-emitting material layer, and at least one of the first electron blocking layer and the third electron blocking layer comprises an amine-based compound having the structure of Formula 5.
  16. In Paragraph 15, An organic light-emitting device comprising at least one hole blocking layer among a first hole blocking layer located between the first light-emitting material layer and the first charge-generating layer, a second hole blocking layer located between the second light-emitting material layer and the second charge-generating layer, and a third hole blocking layer located between the third light-emitting material layer and the second electrode.
  17. In Paragraph 16, An organic light-emitting device comprising at least one hole-blocking layer having an azine-based compound having the structure of Chemical Formula 7 below or a benzimidazole-based compound having the structure of Chemical Formula 9 below. [Chemical Formula 7] In Chemical Formula 7, Y1 to Y5 are each independently CR71 or nitrogen (N), of which 1 to 3 are nitrogen, and R71 is a C6 - C30 aryl; L3 is a C6 - C30 arylene group; R 72 is a C 6 -C 30 aryl or a C 5 -C 30 heteroaryl, and the C 6 -C 30 aryl may be unsubstituted, substituted with another C 6 -C 30 aryl or C 5 -C 30 heteroaryl, or may form a spiro structure with a C 10 -C 30 condensed aryl ring or a C 10 -C 30 condensed heteroaryl ring, and the other C 6 -C 30 aryl may be unsubstituted, substituted with another C 6 -C 30 aryl or another C 5 -C 30 heteroaryl, or may form a spiro structure with a C 10 -C 30 condensed aryl ring; R 73 is hydrogen or adjacent groups combine to form a condensed aromatic ring; f is 0 or 1, g is 1 or 2, and h is an integer from 0 to 4. [Chemical Formula 9] In chemical formula 9, Ar is a C10 - C30 arylene group; R81 is a C6 - C30 aryl or C5 - C30 heteroarylaryl, and the C6 - C30 aryl and C5 - C30 heteroaryl may each be unsubstituted or substituted with a C1 - C10 alkyl; R82 and R83 are each independently hydrogen, a C1 - C10 alkyl, or a C6 - C30 aryl.
  18. In Paragraph 1, Paragraph 9, or Paragraph 14, A red pixel, a green pixel, and a blue pixel are defined on the substrate, and the organic light-emitting diode is positioned to correspond to the red pixel, the green pixel, and the blue pixel. An organic light-emitting device further comprising a color conversion layer located between the substrate and the organic light-emitting diode or on top of the organic light-emitting diode, corresponding to the red pixel, the green pixel, and the blue pixel.
  19. In Paragraph 1, Paragraph 9, or Paragraph 14, A red pixel, a green pixel, and a blue pixel are defined on the substrate, and the organic light-emitting diode is positioned to correspond to the red pixel, the green pixel, and the blue pixel. An organic light-emitting device further comprising a color filter layer located between the substrate and the organic light-emitting diode or on top of the organic light-emitting diode, corresponding to the red pixel, the green pixel, and the blue pixel.

Description

Organic Light Emitting Device The present invention relates to an organic light-emitting device, and more specifically, to an organic light-emitting device in which the light-emitting efficiency and the light-emitting lifespan of the device are significantly improved. As one of the currently widely used flat-panel display devices, organic light-emitting diodes (OLEDs) are attracting attention as display devices that are rapidly replacing liquid crystal display devices (LCDs). Organic light-emitting diodes (OLEDs) are formed from thin organic films of less than 2,000 Å, and depending on the configuration of the electrodes used, they can display images in either a unidirectional or bidirectional manner. Furthermore, since OLEDs can be formed on flexible transparent substrates such as plastic, it is easy to implement flexible or foldable displays. In addition, OLEDs have significant advantages over liquid crystal displays, such as the ability to operate at low voltages and excellent color purity. Conventional fluorescent materials have low luminescence efficiency because only singlet excitons participate in luminescence. Phosphorescent materials, in which triplet excitons also participate in luminescence, have higher luminescence efficiency compared to fluorescent materials. However, metal complexes, which are representative phosphorescent materials, have short luminescence lifetimes, which limits their commercialization. In particular, blue luminescent materials are unsatisfactory in terms of luminescence lifetime and efficiency compared to other colored luminescent materials. Therefore, it is necessary to develop compounds or device structures with improved luminescence efficiency and luminescence lifetime. FIG. 1 is a schematic circuit diagram of an organic light-emitting display device according to an exemplary embodiment of the present invention. FIG. 2 is a cross-sectional view schematically illustrating an organic light-emitting display device as an example of an organic light-emitting device having an organic light-emitting diode according to an exemplary first embodiment of the present invention. FIG. 3 is a cross-sectional view schematically illustrating an organic light-emitting diode having a single organic light-emitting layer, used in an organic light-emitting display device according to an exemplary first embodiment of the present invention. FIG. 4 is a cross-sectional view schematically illustrating an organic light-emitting diode having a double stack structure, used in an organic light-emitting display device according to an exemplary first embodiment of the present invention. FIG. 5 is a cross-sectional view schematically illustrating an organic light-emitting display device according to an exemplary second embodiment of the present invention. FIG. 6 is a cross-sectional view schematically illustrating an organic light-emitting diode having a double stack structure, used in an organic light-emitting display device according to an exemplary second embodiment of the present invention. FIG. 7 is a cross-sectional view schematically illustrating an organic light-emitting diode having a triple stack structure, used in an organic light-emitting display device according to an exemplary second embodiment of the present invention. FIG. 8 is a cross-sectional view schematically illustrating an organic light-emitting display device according to another exemplary third embodiment of the present invention. The present invention will be described below with reference to the attached drawings, where necessary. According to the present invention, by applying an organic compound of a predetermined series to at least one light-emitting unit constituting a light-emitting element, the light-emitting efficiency and light-emitting lifespan of the light-emitting element can be improved. The light-emitting element according to the present invention may be applied to an organic light-emitting device, such as an organic light-emitting display device or a lighting device using an organic light-emitting diode. As an example, a display device using an organic light-emitting diode according to the present invention will be described. FIG. 1 is a schematic circuit diagram of an organic light-emitting display device according to an exemplary embodiment of the present invention. As shown in FIG. 1, in the organic light-emitting display device, gate wiring (GL) and data wiring (DL) and power wiring (PL) are formed intersecting each other to define a pixel area (P), and in the pixel area (P), a switching thin-film transistor (Ts), a driving thin-film transistor (Td), a storage capacitor (Cst), and an organic light-emitting diode (D) are formed. The pixel area (P) may include a red (R) pixel area, a green (G) pixel area, and a blue (B) pixel area. A switching thin-film transistor (Ts) is connected to a gate wire (GL) and a data wire (DL), and a driving thin-film transistor (Td) and a storage capacitor (Cst) are connected betwe