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EP-4741402-A1 - ORGANIC COMPOUND, MIXTURE, COMPOSITION, ORGANIC LIGHT-EMITTING DEVICE, AND DISPLAY PANEL

EP4741402A1EP 4741402 A1EP4741402 A1EP 4741402A1EP-4741402-A1

Abstract

An organic compound having a structure represented by the following formula (1) or (2), where Ar 1 and Ar 2 are independently selected from a substituted or unsubstituted aryl group having 6-60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5-60 carbon atoms; Ar 3 and Ar 4 are independently selected from an aryl group having 6-60 carbon atoms; and at least one of Ar 1 , Ar 2 , Ar 3 , Ar 4 , R 1 , and R 2 contains a linear silanyl group having 1-20 carbon atoms, a branched silanyl group having 1-20 carbon atoms, or a deuterated phenyl group.

Inventors

  • SONG, XINLONG
  • LEI, Jinlong
  • DENG, WENHONG
  • FAN, Huaqiang
  • LIU, FANGYI
  • HE, Ruifeng
  • SONG, Jingyao

Assignees

  • TCL China Star Optoelectronics Technology Co., Ltd.
  • Guangzhou Chinaray Optoelectronic Materials Ltd.

Dates

Publication Date
20260513
Application Date
20251031

Claims (15)

  1. An organic compound, characterized in that the organic compound has a structure represented by the following formula (1) or (2): wherein Ar 1 and Ar 2 are independently selected from a substituted or unsubstituted aryl group having 6-60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5-60 carbon atoms; Ar 3 and Ar 4 are independently selected from an aryl group having 6-60 carbon atoms; R 1 and R 2 are independently selected from -H, -D, a C 1-20 linear alkyl group, a linear silanyl group having 1-20 carbon atoms, a branched silanyl group having 1-20 carbon atoms, a linear alkoxyl group having 1-20 carbon atoms, a linear thioalkoxyl group having 1-20 carbon atoms, a C 3-20 branched alkyl group, a C 3-20 cyclic alkyl group, a branched alkoxyl group having 3-20 carbon atoms, a cyclic alkoxyl group having 3-20 carbon atoms, a branched thioalkoxyl group having 3-20 carbon atoms, a cyclic thioalkoxyl group having 3-20 carbon atoms, a ketone group having 1-20 carbon atoms, an alkoxycarbonyl group having 2-20 carbon atoms, an aryloxycarbonyl group having 7-20 carbon atoms, an alkenyl group having 2-20 carbon atoms, a cyanoyl group, a carbamoyl group, a haloformyl group, a formyl group, an isocyanoyl group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, -CF 3 , -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6-30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5-30 ring atoms, a substituted or unsubstituted aryloxy group having 6-30 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5-30 ring atoms; at least one of Ar 1 , Ar 2 , Ar 3 , Ar 4 , R 1 , and R 2 contains a linear silanyl group having 1-20 carbon atoms, a branched silanyl group having 1-20 carbon atoms, or a deuterated phenyl group; n1 is independently selected from 0, 1, 2, or 3; and n2 is independently selected from 0, 1, 2, 3, or 4.
  2. The organic compound of claim 1, characterized in that Ar 1 is a group represented by any one of the following formulae (X-1) to (X-4): Ar 2 is a group represented by any one of the following formulae (A-1) to (A-4): and Ar 3 and Ar 4 are independently a group represented by any one of the following formulae (B-1) to (B-5): wherein a linking site of Ar 2 is a carbon atom of a of Ar 2 , a linking site of Ar 3 is a carbon atom of a ring of Ar 3 , and a fused site of Ar 4 is two adjacent carbon atoms of a ring of Ar 4 ; X is selected from O, S, N-CH 3 , N-Ph, or C(CH 3 ) 2 ; R 0 and L independently have the same definitions as those for R 1 and R 2 ; n0 is any integer from 0 to 14; a is any integer from 0 to 12; and --- in the formulae (X-1) to (X-4) refers to a bond to connect with the formula (1) or (2).
  3. The organic compound of claim 2, characterized in that Ar 1 is the group represented by the formula (X-2), and Ar 4 is the group represented by any one of the formulae (B-2) to (B-5).
  4. The organic compound of claim 2, characterized in that Ar 2 is the group represented by any one of the following formulae: wherein L and a in the formulae independently have the same definitions as those for L and a in the formulae (A-1) to (A-4).
  5. The organic compound of claim 2, characterized in that n1 is greater than or equal to 2, and adjacent two R 1 groups and ring atoms connected thereto form a ring or do not form a ring together; n2 is greater than or equal to 2, and adjacent two R 2 groups and ring atoms connected thereto form a ring or do not form a ring together; and a is greater than or equal to 2, and adjacent two L groups and atoms connected thereto form or do not form a ring with each other.
  6. The organic compound of claim 1, characterized in that the organic compound has the structure represented by any one of the following formulae (2-1) to (2-31): wherein R 1 , R 2 , R 3 , R 4 , and L in the formulae (2-1) to (2-31) independently have the same definitions as those for R 1 and R 2 in the formula (1) and formula (2); a is any integer from 0 to 12; n0 is any integer from 0 to 14; n1 and n2 in the formulae (2-1) to (2-31) independently have the same definitions as those for n1 and n2 in the formula (1) and formula (2); n3 is greater than or equal to 0 and less than or equal to 5, wherein adjacent two R 3 groups and ring atoms connected thereto form a ring or do not form a ring together in response to n3 being greater than or equal to 2; and n4 is greater than or equal to 0 and less than or equal to 5, wherein adjacent two R 4 groups and ring atoms connected thereto form a ring or do not form a ring together in response to n4 being greater than or equal to 2.
  7. The organic compound of claim 6, characterized in that R 1 , R 2 , R 3 , R 4 , and L are independently selected from -H, -D, a C 1-10 linear alkyl group, a C 3-10 branched alkyl group, or a C 3-10 cyclic alkyl group.
  8. The organic compound of claim 6, characterized in that R 1 , R 2 , R 3 , R 4 , and L are independently selected from -H, -D, a C 1-4 linear alkyl group or a C 3-5 branched alkyl group.
  9. The organic compound of claim 1, characterized in that the organic compound is a blue light-emitting material.
  10. The organic compound of claim 1, characterized in that the organic compound is selected from any one of a group consisting of the following compounds 1 to 168:
  11. A mixture, characterized in that the mixture comprises the organic compound as claimed in any one of claims 1 to 10 and at least one organic functional material, and the organic functional material is selected from a group consisting of a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, a light-emitting material, a host material, and an organic dye.
  12. A composition, characterized in that the composition comprises the organic compound as claimed in any one of claims 1 to 10 and at least one organic solvent, or the composition comprises the mixture as claimed in claim 10 and the at least one organic solvent.
  13. An organic light-emitting device, characterized in that the organic light-emitting device comprises: a first electrode; a second electrode disposed opposite to the first electrode; and an organic functional layer disposed between the first electrode and the second electrode, wherein the organic functional layer comprises one or more organic compound as claimed in any one of claims 1 to 10, or the organic functional layer comprises the mixture as claimed in claim 11, or the organic functional layer comprises the composition as claimed in claim 12.
  14. The organic light-emitting device of claim 11, characterized in that the organic functional layer further comprises a light-emitting layer comprising a host material and a guest material, wherein the guest material comprises one or more organic compounds.
  15. A display panel, characterized in that the display panel comprises the organic light-emitting device as claimed in claim 13 or 14.

Description

TECHNICAL FIELD The present application relates to the field of display technologies, and in particular, to an organic compound, a mixture, a composition, an organic light-emitting device, and a display panel. BACKGROUND At present, an organic electroluminescent device includes an anode, a cathode, and an organic layer disposed between the anode and the cathode. Organic substances in the organic layer convert electrical energy into light energy to achieve organic electroluminescence. In order to improve the luminous efficiency and service life of the organic electroluminescent device, the organic layer is often composed of multiple layers and organic compounds in different layer are different. Specifically, the organic layer includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like. A voltage is applied between the anode and the cathode of the organic electroluminescent device, holes in the anode are injected into the organic layer, and electrons in the cathode are injected into the organic layer, the injected holes meet with the injected electrons to form excitons, and the excitons emit light when transitioning back to the ground state, thereby achieving the luminescence of the organic electroluminescent device. The organic electroluminescent device has wide application prospect due to its characteristics of autonomous luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast ratio, high responsiveness, and the like. In order to improve the luminous efficiency of the organic electroluminescent device, various light-emitting material systems based on fluorescence and phosphorescence have been developed. The organic electroluminescent device using a fluorescence material has the characteristic of high reliability, but its internal electroluminescence quantum efficiency is limited to 25% under electrical excitation due to the fact that the branch ratio of excitons in a singlet excited-state and a triplet excited-state is 1:3. The organic electroluminescent device using a phosphorescence material has achieved almost 100% internal electroluminescence quantum efficiency. However, the phosphorescence material is a metal complex containing iridium and platinum that are expensive raw materials, the synthesis of the metal complex is complicated, and the organic electroluminescent device using the phosphorescence material may produce a roll-off effect, that is, the luminous efficiency of the organic electroluminescent device using the phosphorescence material may rapidly decrease with an increase of current or brightness, which limit the use of the phosphorescence material in the organic electroluminescent device at high brightness. Furthermore, in order to solve the above problems, at present, light-emitting materials usually use a combination of various materials based on organic compounds, such as a composite excited state material, a thermally activated delayed fluorescence (TADF) material, and the like, attempting to achieve higher luminous efficiency of the organic electroluminescent device comparable to the organic electroluminescent device using the phosphorescence material by using reverse internal conversion. However, the improvement of properties of traditional organic compounds including the TADF material is limited in terms of luminous efficiency and service life, making it difficult to improve the luminous efficiency and service life of the organic electroluminescent device using the organic compound including the TADF material. SUMMARY The present application provides an organic compound, a mixture, a composition, an organic light-emitting device, and a display panel, which can improve the luminous efficiency and the service life of the organic light-emitting device. The present application is set out in the appended set of claims. By introducing aromatic rings and at least one of a silanyl group and a deuterated phenyl group into the organic compound, the embodiments of the present application effectively increase the relative molecular mass of the organic compound, make the molecular configuration and the molecular gap of the organic compound larger, and enable the organic compound to have better solubility, thereby facilitating the purification of the organic compound in the preparation process, improving the purity of the organic compound, and improving the luminous efficiency and service life of an organic light-emitting device using the organic compound. BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is a hydrogen nuclear magnetic resonance spectra (HNMR) of an organic compound M165 according to some embodiments of the present application.FIG. 2 is a HNMR of an organic compound M166 according to some embodiments of the present application.FIG. 3 is a HNMR of an organic compound M167 according to some embodiments of the present application.FIG. 4 is a schematic struc