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KR-102961583-B1 - ORGANIC COMPOUND, ORGANIC LIGHT EMITTING DIODE AND ORGANIC LIGHT EMITTING DEVICE INCLUDING THE COMPOUND

KR102961583B1KR 102961583 B1KR102961583 B1KR 102961583B1KR-102961583-B1

Abstract

The present invention relates to an organic compound having the structure of Chemical Formula 1 below, and to an organic light-emitting diode and an organic light-emitting device in which said organic compound is introduced into a light-emitting layer. In said organic compound, an electron donor triazine moiety and an electron acceptor condensed heteroaromatic moiety are separated by an aromatic ring. By including an electron donor moiety and an electron acceptor moiety within a single molecule, they can move easily within the molecule. Furthermore, because it includes a rigid condensed heteroaromatic ring, the three-dimensional structure of the molecule is limited, allowing for excellent luminous efficiency and color purity. [Chemical Formula 1]

Inventors

  • 김준연
  • 최형종
  • 양중환
  • 서보민
  • 홍태량
  • 김진희
  • 신은철

Assignees

  • 엘지디스플레이 주식회사
  • 솔브레인 주식회사

Dates

Publication Date
20260507
Application Date
20201016
Priority Date
20191128

Claims (20)

  1. An organic compound having the structure of Chemical Formula 1 below. [Chemical Formula 1] In Chemical Formula 1, R1 to R12 are each independently light hydrogen, deuterium, tritium, a halogen atom, a cyano group, a C1 - C20 alkyl group, a C1 - C20 alkoxy group, a C1 - C20 alkyl amino group, a C6 - C30 aromatic functional group, or a C3 - C30 heteroaromatic functional group, or two adjacent R1 to R12 are combined to form a C6 - C20 aromatic ring or a C3 - C30 heteroaromatic ring, and at least one of R1 to R4 is a cyano group; R 13 to R 15 are each independently light hydrogen, deuterium, tritium, C 1 -C 20 alkyl group, C 1 -C 20 alkoxy group, C 1 -C 20 alkyl amino group, C 6 -C 30 aromatic functional group, or C 3 -C 30 heteroaromatic functional group, and A is a condensed heteroaromatic ring having the structure of Chemical Formula 2 below. [Chemical Formula 2] In Chemical Formula 2, R21 to R24 are each independently a light hydrogen, deuterium, tritium, a halogen atom, a cyano group, a C1 - C20 alkyl group, a C1 - C20 alkoxy group, a C1 - C20 alkyl amino group, a C6 - C30 aromatic functional group, or a C3 - C30 heteroaromatic functional group, or two adjacent R21 to R24 are combined to form a C6 - C20 aromatic ring or a C3 - C30 heteroaromatic ring; X is NR 25 , an oxygen atom (O), or a sulfur atom (S), and R 25 is light hydrogen, deuterium, tritium, C 1 -C 20 alkyl group, C 1 -C 20 alkoxy group, C 1 - C 20 alkyl amino group, C 6 -C 30 aromatic functional group, or C 3 -C 30 heteroaromatic functional group; dashed lines indicate portions that condense with adjacent nitrogen-containing 5-membered rings of Formula 1, respectively.
  2. In claim 1, the organic compound is an organic compound having the structure of the following chemical formula 3. [Chemical Formula 3] In Chemical Formula 3, R1 to R15 are each identical to those defined in Chemical Formula 1, R21 and R22 are each identical to those defined in Chemical Formula 2, and B is a condensed heteroaromatic ring having the structure of Chemical Formula 4 below. [Chemical Formula 4] In Chemical Formula 4, R 23 and R 24 are each the same as defined in Chemical Formula 2; the dotted line of the 5-membered ring containing X represents the portion condensed with the lateral benzene ring constituting the carbazole moiety of Chemical Formula 3, and the dotted line of the 6-membered ring represents the portion condensed with the 5-membered ring constituting the indole moiety of Chemical Formula 3.
  3. In claim 1, the organic compound is an organic compound having the structure of the following chemical formula 5. [Chemical Formula 5] In Chemical Formula 5, R1 to R15 are each identical to those defined in Chemical Formula 1, R21 and R22 are each identical to those defined in Chemical Formula 2, and B is a condensed heteroaromatic ring having the structure of Chemical Formula 6 below. [Chemical Formula 6] In Chemical Formula 6, R 23 and R 24 are each identical to those defined in Chemical Formula 2; the dotted line of the 5-membered ring containing X represents the portion condensed with the lateral benzene ring constituting the carbazole moiety of Chemical Formula 5, and the dotted line of the 6-membered ring represents the portion condensed with the 5-membered ring constituting the indole moiety of Chemical Formula 5.
  4. In claim 1, the organic compound is an organic compound having the structure of the following chemical formula 7. [Chemical Formula 7] In Chemical Formula 7, R1 to R15 are each identical to those defined in Chemical Formula 1, R21 and R22 are each identical to those defined in Chemical Formula 2, and B is a condensed heteroaromatic ring having the structure of Chemical Formula 8 below. [Chemical Formula 8] In Chemical Formula 8, R 23 and R 24 are each the same as defined in Chemical Formula 2; the dashed line of the pentatonic ring containing X represents the portion condensed with the lateral benzene ring constituting the carbazolel moiety of Chemical Formula 7, and the dashed line of the benzene ring represents the portion condensed with the pentatonic ring constituting the indole moiety of Chemical Formula 7.
  5. In claim 1, the organic compound is an organic compound comprising any one of the organic compounds having the structure of the following chemical formula 9. [Chemical Formula 9]
  6. In claim 1, the organic compound is an organic compound comprising any one of the organic compounds having the structure of the following chemical formula 10. [Chemical Formula 10]
  7. In claim 1, the organic compound is an organic compound comprising any one of the organic compounds having the structure of the following chemical formula 11. [Chemical Formula 11]
  8. First electrode; A second electrode facing the first electrode; and It includes a light-emitting material layer located between the first and second electrodes, and The above-mentioned light-emitting material layer is an organic light-emitting diode comprising an organic compound having the structure of Chemical Formula 1 below. [Chemical Formula 1] In Chemical Formula 1, R1 to R12 are each independently light hydrogen, deuterium, tritium, a halogen atom, a cyano group, a C1 - C20 alkyl group, a C1 - C20 alkoxy group, a C1 - C20 alkyl amino group, a C6 - C30 aromatic functional group, or a C3 - C30 heteroaromatic functional group, or two adjacent R1 to R12 are combined to form a C6 - C20 aromatic ring or a C3 - C30 heteroaromatic ring, and at least one of R1 to R4 is a cyano group; R 13 to R 15 are each independently light hydrogen, deuterium, tritium, C 1 -C 20 alkyl group, C 1 -C 20 alkoxy group, C 1 -C 20 alkyl amino group, C 6 -C 30 aromatic functional group, or C 3 -C 30 heteroaromatic functional group, and A is a condensed heteroaromatic ring having the structure of Chemical Formula 2 below. [Chemical Formula 2] In Chemical Formula 2, R21 to R24 are each independently a light hydrogen, deuterium, tritium, a halogen atom, a cyano group, a C1 - C20 alkyl group, a C1 - C20 alkoxy group, a C1 - C20 alkyl amino group, a C6 - C30 aromatic functional group, or a C3 - C30 heteroaromatic functional group, or two adjacent R21 to R24 are combined to form a C6 - C20 aromatic ring or a C3 - C30 heteroaromatic ring; X is NR 25 , an oxygen atom (O), or a sulfur atom (S), and R 25 is light hydrogen, deuterium, tritium, C 1 -C 20 alkyl group, C 1 -C 20 alkoxy group, C 1 - C 20 alkyl amino group, C 6 -C 30 aromatic functional group, or C 3 -C 30 heteroaromatic functional group; dashed lines indicate portions that condense with adjacent nitrogen-containing 5-membered rings of Formula 1, respectively.
  9. In claim 8, the organic compound is an organic light-emitting diode having the structure of the following chemical formula 3. [Chemical Formula 3] In Chemical Formula 3, R1 to R15 are each identical to those defined in Chemical Formula 1, R21 and R22 are each identical to those defined in Chemical Formula 2, and B is a condensed heteroaromatic ring having the structure of Chemical Formula 4 below. [Chemical Formula 4] In Chemical Formula 4, R 23 and R 24 are each the same as defined in Chemical Formula 2; the dotted line of the 5-membered ring containing X represents the portion condensed with the lateral benzene ring constituting the carbazole moiety of Chemical Formula 3, and the dotted line of the 6-membered ring represents the portion condensed with the 5-membered ring constituting the indole moiety of Chemical Formula 3.
  10. In claim 8, the organic compound is an organic light-emitting diode having the structure of the following chemical formula 5. [Chemical Formula 5] In Chemical Formula 5, R1 to R15 are each identical to those defined in Chemical Formula 1, R21 and R22 are each identical to those defined in Chemical Formula 2, and B is a condensed heteroaromatic ring having the structure of Chemical Formula 6 below. [Chemical Formula 6] In Chemical Formula 6, R 23 and R 24 are each the same as defined in Chemical Formula 2; the dashed line of the 5-membered ring containing X represents the portion condensed with the lateral benzene ring constituting the carbazole moiety of Chemical Formula 5, and the dashed line of the 6-membered ring represents the portion condensed with the 5-membered ring constituting the indole moiety of Chemical Formula 5.
  11. In claim 8, the organic compound is an organic light-emitting diode having the structure of the following chemical formula 7. [Chemical Formula 7] In Chemical Formula 7, R1 to R15 are each identical to those defined in Chemical Formula 1, R21 and R22 are each identical to those defined in Chemical Formula 2, and B is a condensed heteroaromatic ring having the structure of Chemical Formula 8 below. [Chemical Formula 8] In Chemical Formula 8, R 23 and R 24 are each the same as defined in Chemical Formula 2; the dashed line of the 5-membered ring containing X represents the portion condensed with the lateral benzene ring constituting the carbazole moiety of Chemical Formula 7, and the dashed line of the 6-membered ring represents the portion condensed with the 5-membered ring constituting the indole moiety of Chemical Formula 7.
  12. In claim 8, the light-emitting material layer comprises a first compound and a second compound, and the second compound is an organic light-emitting diode comprising the organic compound.
  13. In claim 12, an organic light-emitting diode in which the excited triplet energy level of the first compound is higher than the excited triplet energy level of the second compound.
  14. In claim 12, the above-mentioned light-emitting material layer further comprises a third compound in an organic light-emitting diode.
  15. In claim 14, the organic light-emitting diode in which the excitation singlet energy level of the third compound is lower than the excitation singlet energy level of the second compound.
  16. In claim 12, the emitting material layer comprises a first emitting material layer located between the first electrode and the second electrode, and a second emitting material layer located between the first electrode and the first emitting material layer or between the first emitting material layer and the second electrode, wherein the first emitting material layer comprises the first compound and the second compound, and the second emitting material layer comprises the fourth compound and the fifth compound, forming an organic light-emitting diode.
  17. In claim 16, the excited triplet energy level of the fourth compound is higher than the excited triplet energy level of the second compound, and An organic light-emitting diode in which the excitation singlet energy level of the fifth compound is lower than the excitation singlet energy level of the second compound.
  18. An organic light-emitting diode according to claim 16, further comprising a third light-emitting material layer located opposite the second light-emitting material layer with respect to the first light-emitting material layer, wherein the third light-emitting material layer comprises a sixth compound and a seventh compound.
  19. In paragraph 18, the excited triplet energy level of the 6th compound is higher than the excited triplet energy level of the 2nd compound, and An organic light-emitting diode in which the excitation singlet energy level of the above-mentioned seventh compound is lower than the excitation singlet energy level of the above-mentioned second compound.
  20. Substrate; and An organic light-emitting diode positioned on the above substrate and described in any one of claims 8 to 19 An organic light-emitting device including

Description

Organic compound, organic light-emitting diode and organic light-emitting device including the same The present invention relates to organic compounds, and more specifically, to organic compounds having excellent luminescence properties, organic light-emitting diodes containing the same, and organic light-emitting devices. Organic light-emitting diodes (OLEDs), one of the planar display devices, are attracting attention as light-emitting devices that are rapidly replacing liquid crystal display devices. Organic light-emitting diodes (OLEDs) are formed from thin organic films of less than 2,000 Å, and can realize images in either a single direction or both directions depending on the configuration of the electrodes used. In addition, since OLEDs can be formed on flexible transparent substrates such as plastic, it is easy to realize flexible or foldable display devices. Furthermore, OLED displays have significant advantages over liquid crystal displays, such as the ability to operate at low voltages and excellent color purity. Organic light-emitting diodes emit light when holes injected from the anode and electrons injected from the cathode combine in the light-emitting material layer to form excitons, which enter an unstable energy state (excited state) and then return to a stable ground state. 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 limitations in commercialization due to their short luminescence lifetime. Furthermore, organic compounds developed to achieve blue luminescence have the problem of not only having poor luminescence characteristics but also a short luminescence lifetime. FIG. 1 is a schematic diagram showing the luminescence mechanism of an organic compound according to an exemplary first 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 according to the present invention. FIG. 3 is a schematic cross-sectional view of an organic light-emitting diode according to an exemplary first embodiment of the present invention. FIG. 4 is a schematic diagram showing the light emission mechanism according to the energy levels between light-emitting materials in a light-emitting material layer constituting an organic light-emitting diode according to an exemplary first embodiment of the present invention. FIG. 5 is a schematic cross-sectional view of an organic light-emitting diode according to an exemplary second embodiment of the present invention. FIG. 6 is a schematic diagram showing the light emission mechanism according to the energy levels between light-emitting materials in a light-emitting material layer constituting an organic light-emitting diode according to an exemplary second embodiment of the present invention. FIG. 7 is a schematic cross-sectional view of an organic light-emitting diode according to an exemplary third embodiment of the present invention. FIG. 8 is a schematic diagram showing the light emission mechanism according to the energy levels between light-emitting materials in a light-emitting material layer constituting an organic light-emitting diode according to an exemplary third embodiment of the present invention. FIG. 9 is a schematic cross-sectional view of an organic light-emitting diode according to an exemplary fourth embodiment of the present invention. FIG. 10 is a schematic diagram showing the light emission mechanism according to the energy levels between light-emitting materials in a light-emitting material layer constituting an organic light-emitting diode according to an exemplary fourth embodiment of the present invention. FIG. 11 is a schematic cross-sectional view of an organic light-emitting diode according to an exemplary fifth embodiment of the present invention. FIG. 12 is a cross-sectional view schematically showing an organic light-emitting display device as an example of an organic light-emitting device according to an exemplary second embodiment of the present invention. FIG. 13 is a schematic cross-sectional view of an organic light-emitting diode according to an exemplary sixth embodiment of the present invention. FIG. 14 is a cross-sectional view schematically showing an organic light-emitting display device as an example of an organic light-emitting device according to an exemplary third embodiment of the present invention. FIG. 15 is a schematic cross-sectional view of an organic light-emitting diode according to an exemplary seventh embodiment of the present invention. FIG. 16 is a schematic cross-sectional view of an organic light-emitting diode according to an exemplary eighth embodiment of th