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CN-122011006-A - Luminescent material, organic electroluminescent device and preparation method

CN122011006ACN 122011006 ACN122011006 ACN 122011006ACN-122011006-A

Abstract

The invention discloses a luminescent material, an organic electroluminescent device and a preparation method thereof, and relates to the technical field of organic electroluminescence. The structural general formula of the luminescent material is shown as formula (1) or formula (2): Ar 1 、Ar 2 、Ar 5 is independently substituted or unsubstituted C 6 -C 60 aryl or substituted or unsubstituted C 4 -C 60 heteroaryl, ar 3 is a group containing triphenylsilane and having a total number of carbon atoms of 18-160, and Ar 4 is selected from one of the following structures: 、 、 、 、 And . The luminescent material provided by the invention is a pure green luminescent material, and has high color purity, high efficiency, high stability, good solubility and film forming suitability.

Inventors

  • YANG CHULUO
  • HU YUXUAN
  • Xue Zhuixing

Assignees

  • 深圳大学

Dates

Publication Date
20260512
Application Date
20260202

Claims (10)

  1. 1. The luminescent material is characterized in that the structural general formula of the luminescent material is shown as formula (1) or formula (2): Wherein Ar 1 、Ar 2 、Ar 5 is independently substituted C 6 -C 60 aryl, unsubstituted C 6 -C 60 aryl, substituted C 4 -C 60 heteroaryl, or unsubstituted C 4 -C 60 heteroaryl; ar 3 is a group containing triphenylsilane and having a total number of carbon atoms of 18 to 160; ar 4 is selected from one of the following structures: 、 、 、 、 And ; X 1 、X 2 、X 3 、X 4 、X 5 are each independently selected from a single bond, O, S, se, CR a R b 、SiR a R b 、NR c , and when X 1 , X 2 or X 3 is a single bond, it can be condensed with Ar 1 , ar 2 or Ar 5 to form a five-membered ring, R a 、R b 、R c is each independently selected from H, D, F, cl, br, I, benzyl, ester, amide, carbonyl, aldehyde, nitro, unsubstituted C 1 -C 30 alkyl, substituted C 1 -C 30 alkyl, unsubstituted C 1 -C 10 alkoxy, Substituted C 1 -C 10 alkoxy, unsubstituted C 3 -C 30 cycloalkyl, substituted C 3 -C 30 cycloalkyl, unsubstituted C 1 -C 30 alkylthio, Substituted C 1 -C 30 alkylthio, unsubstituted C 6 -C 30 aryl, substituted C 6 -C 30 aryl, unsubstituted C 4 -C 30 heteroaryl, one of the substituted C 4 -C 30 heteroaryl groups; representing the ligation site.
  2. 2. The luminescent material according to claim 1, wherein Ar 3 is selected from one of the following structures: 、 、 、 、 And ; Wherein R2 to R8 are located at any connectable position on the respective benzene rings, R2 to R8 are mono-or polysubstituted, each independently selected from at least one of the following groups: H、D、 、 、 、 、 And ; Wherein, the And represents a linking site, wherein R9 and R10 are located at any attachable position on the respective benzene rings, and R9 and R10 are each independently selected from one of H, D, F, cl, br, I, benzyl, ester, amide, carbonyl, aldehyde, nitro, unsubstituted C 1 -C 30 alkyl, substituted C 1 -C 30 alkyl, unsubstituted C 1 -C 10 alkoxy, substituted C 1 -C 10 alkoxy, unsubstituted C 1 -C 10 alkylamino, substituted C 1 -C 10 alkylamino, unsubstituted C 3 -C 10 cycloalkyl, substituted C 3 -C 10 cycloalkyl, unsubstituted C 1 -C 30 alkylthio, substituted C 1 -C 30 alkylthio, unsubstituted C 6 -C 30 aryl, substituted C 6 -C 30 aryl, unsubstituted C 4 -C 30 heteroaryl, and substituted C 4 -C 30 heteroaryl.
  3. 3. The luminescent material according to claim 1, wherein the substituents in the substituted C 6 -C 60 aryl group, the substituted C 4 -C 60 heteroaryl group are each independently selected from one of H, D, F, cl, br, I, a nitrile group, an acyl group, an unsubstituted C 1 -C 30 alkyl group, a substituted C 1 -C 30 alkyl group, an unsubstituted C 1 -C 10 alkoxy group, a substituted C 1 -C 10 alkoxy group, an unsubstituted C 3 -C 30 cycloalkyl group, a substituted C 3 -C 30 cycloalkyl group, an unsubstituted C 1 -C 30 alkylthio group, a substituted C 1 -C 30 alkylthio group, an unsubstituted C 6 -C 30 aryl group, a substituted C 6 -C 30 aryl group, an unsubstituted C 4 -C 30 heteroaryl group, and a substituted C 4 -C 30 heteroaryl group.
  4. 4. The luminescent material according to claim 1, wherein Ar 1 、Ar 2 and Ar 5 are each independently selected from one of the following structures: ; Wherein, the R11 represents a connecting site, and R11 is located at any connectable position on a benzene ring where the R11 is located in different structural formulas, and each R11 in the different structural formulas is independently selected from one of H, D, F, cl, br, I, cyano, benzyl, ester, amido, carbonyl, aldehyde, nitro, substituted amino, unsubstituted amino, substituted borane, unsubstituted borane, substituted C 1 -C 30 alkyl, unsubstituted C 1 -C 30 alkyl, substituted C 1 -C 10 alkoxy, unsubstituted C 1 -C 10 alkoxy, substituted C 1 -C 10 alkylamino, unsubstituted C 1 -C 10 alkylamino, substituted C 3 -C 30 cycloalkyl, unsubstituted C 3 -C 30 cycloalkyl, substituted C 1 -C 30 alkylthio, unsubstituted C 1 -C 30 alkylthio, substituted C 6 -C 30 aryl, unsubstituted C 6 -C 30 aryl, substituted C 4 -C 30 heteroaryl and unsubstituted C 4 -C 30 heteroaryl.
  5. 5. The luminescent material according to claim 1, wherein the luminescent material is selected from one of the following structures: 。
  6. 6. A method of producing a luminescent material as claimed in any one of claims 1 to 5, characterized by comprising the steps of: Will be And (3) with Or (b) After the reaction, obtain I.e., the luminescent material, or, Will be And (3) with Or (b) After the reaction, obtain I.e. the luminescent material; Wherein X is halogen.
  7. 7. An organic electroluminescent device comprising a first electrode, a light-emitting layer and a second electrode, which are sequentially stacked, wherein the light-emitting layer comprises the light-emitting material according to any one of claims 1 to 5.
  8. 8. The organic electroluminescent device according to claim 7, wherein the organic electroluminescent device comprises a refractive layer, a first electrode, an electron injection layer, an electron transport layer, a light emitting layer, a hole transport layer, a hole injection layer, and a second electrode, which are sequentially stacked; The light emitting layer comprises a host material, an exciton sensitization material and a guest material, wherein the host material comprises a heat-activated delayed fluorescence material, the exciton sensitization material comprises a complex containing a metal element, and the guest material comprises the light emitting material; The mass ratio of the host material to the exciton sensitization material to the guest material is (60-94.5) (5-30) (0.5-5).
  9. 9. A method for producing an organic electroluminescent device as claimed in any one of claims 7 to 8, comprising the steps of: Providing a second electrode; and forming a light-emitting layer and a first electrode on the second electrode in sequence to obtain the organic electroluminescent device.
  10. 10. The preparation method according to claim 9, characterized in that it comprises the following steps: Providing a second electrode; And sequentially forming an electron transport layer, an electron injection layer, a first electrode and a refraction layer on the light-emitting layer by a vacuum evaporation method.

Description

Luminescent material, organic electroluminescent device and preparation method Technical Field The invention relates to the technical field of organic electroluminescence, in particular to a luminescent material, an organic electroluminescent device and a preparation method. Background In the field of photoelectricity, organic electroluminescent devices (OLEDs) are attracting attention due to high brightness, high contrast and good color saturation, and have been widely used in the fields of mobile phones, televisions, vehicle-mounted displays, and the like. For ultra-high definition display, the luminescent material not only needs to have a narrow emission full width at half maximum (FWHM) to obtain high color purity, but also needs to maintain good thermal stability and device life under high brightness driving. However, the existing fluorescence, phosphorescence and traditional Thermally Activated Delayed Fluorescence (TADF) materials are generally wide in emission band and obvious in vibration structure, and often depend on an optical filter to improve the color purity, so that the photon utilization rate is reduced, and the efficiency and the service life of the device are limited. In recent years, multiple resonance heat-activated delayed fluorescence (MR-TADF) materials developed based on B/N atom doped polycyclic aromatic hydrocarbon benefit from having a rigid structural skeleton and localized electronic properties, can obtain efficient narrow band emission, and are considered as powerful candidate materials for next-generation high-color-gamut display. However, the conventional MR-TADF materials still face several key challenges in practical device applications, such as luminescence quenching caused by intermolecular stacking and aggregation, and problems of efficiency roll-off and lifetime decay under high brightness driving, so that it is still difficult to simultaneously achieve high color purity, high efficiency and device stability. Therefore, there is a need to develop a luminescent material system that combines high color purity, high efficiency and high stability, and to improve its suitability in devices, especially in solution processing and inkjet printing processes. Accordingly, the prior art is still in need of improvement and development. Disclosure of Invention Based on the above-mentioned shortcomings of the prior art, the present invention aims to provide a luminescent material, an organic electroluminescent device and a preparation method thereof, and aims to provide a luminescent material with high color purity, high efficiency and high stability. The technical scheme of the invention is as follows: In a first aspect of the present invention, a luminescent material is provided, where the structural general formula of the luminescent material is shown in formula (1) or formula (2): Wherein Ar 1、Ar2、Ar5 is independently substituted C 6-C60 aryl, unsubstituted C 6-C60 aryl, substituted C 4-C60 heteroaryl, or unsubstituted C 4-C60 heteroaryl; ar 3 is a group containing triphenylsilane and having a total number of carbon atoms of 18 to 160; ar 4 is selected from one of the following structures: 、、、、 And ; X 1、X2、X3、X4、X5 are each independently selected from a single bond, O, S, se, CR aRb、SiRaRb、NRc, and when X 1, X 2 or X 3 is a single bond, it can be condensed with Ar 1, ar 2 or Ar 5 to form a five-membered ring, R a、Rb、Rc is each independently selected from H, D (deuterium), F, cl, br, I, benzyl, ester, amide, carbonyl, aldehyde, nitro, unsubstituted C 1-C30 alkyl, substituted C 1-C30 alkyl (such as trifluoromethyl), and, Unsubstituted C 1-C10 alkoxy, substituted C 1-C10 alkoxy, unsubstituted C 3-C30 cycloalkyl, substituted C 3-C30 cycloalkyl, Unsubstituted C 1-C30 alkylthio, substituted C 1-C30 alkylthio, unsubstituted C 6-C30 aryl, substituted C 6-C30 aryl, One of unsubstituted C 4-C30 heteroaryl, substituted C 4-C30 heteroaryl; representing the ligation site. The luminescent material provided by the invention is a pure green light luminescent material with high color purity, high efficiency, high stability, good solubility and film forming suitability, and particularly, the luminescent material is a multiple resonance type compound, has a rigid multiple resonance molecular skeleton and shows narrow-band green light emission. According to the invention, the non-conjugated three-dimensional structural unit of triphenylsilane and the triphenylsilane derivative is introduced into the structure of the luminescent material, so that the morphology stability and the thermal stability of the material can be improved, the solubility and the solution film forming performance can be improved while the pure green light emission characteristic of the narrow band of the boron-based resonance skeleton is maintained, and on the other hand, the intermolecular accumulation can be greatly weakened, the harmful intermolecular aggregation and aggregation-induced non-radiative decay (namely