Hole transport material, manufacturing method thereof, and electroluminescent device thereof

Patent metadata

Field	Value
Publication number	US-2020403162-A1
Application number	US-201916629970-A
Country	US
Kind code	A1
Filing date	Nov 12, 2019
Priority date	Jun 24, 2019
Publication date	Dec 24, 2020
Grant date	—

Abstract

The present invention adjusts the structure of donor units to change a capability of providing electrons thereof, designs a hole transport material of a high mobility and reasonable wires, and the material improves the compounding efficiency.

First claim

What is claimed is:

1 . A method for manufacturing a hole transport material, comprising:
step 1) proportionally adding raw materials including a central core raw material and an electron donor, and mixing the raw materials with a solvent as a reaction solution; step 2) adding a catalyst of palladium (II) acetate (Pd(OAc) 2 ) and a tri-tert-butylphosphine tetrafluoroborate into the reaction solution, and adding toluene free of water and oxygen under an atmosphere of argon gas in the reaction solution, heating the raw materials, the solvent, the catalyst, and the toluene in the reaction solution for reaction by 20-24 hours, and cooling the reaction solution to a room temperature; step 3) pouring the reaction solution into ice water, extracting extracts of organic phase three times by dichloromethane to combine the extract of organic phase, and spinning the extracts of organic phase combined to form silicone; and step 4) implementing separation and purification of column chromatography to acquire white powder to acquire a finished product of the hole transport material; wherein the hole transport material comprises a central core made of tetramethyldihydrophenazine, a structural formula of the hole transport material is

and each of the R 1 group and the R 2 group is selected from structural formulas as follows:

and the hole transport material is selected from compounds as follows:

2 . The method for manufacturing a hole transport material as claimed in claim 1 , wherein the hole transport material is composed of tetramethyldihydrophenazine including an electron donor and an electron donor in a periphery, and a structural formula of the central core is as follows:

the electron donor is selected from

(carbazole),

(diphenylamine), and

(9,9′-dimethylacridine).

3 . The method for manufacturing a hole transport material as claimed in claim 1 , wherein the step 2) adds toluene free of water and oxygen under an atmosphere of argon gas in the reaction solution, for reaction at 120° C. by 24 hours, and cools the reaction solution to a room temperature.

4 . The method for manufacturing a hole transport material as claimed in claim 1 , wherein the central core is

an input amount of the central core is 2.73 g, and a molar amount of the central core is 5 mmol.

5 . The method for manufacturing a hole transport material as claimed in claim 1 , wherein an input amount of the electron donor is 2.0-2.5 g, a molar amount of the electron donor is 12 mmol, an input amount of the palladium (II) acetate is 0.18 g, an molar amount of the palladium (II) acetate is 0.8 mmol, an input amount of the tri-tert-butylphosphine tetrafluoroborate is 0.68 g, and a molar amount of the tri-tert-butylphosphine tetrafluoroborate is 2.4 mmol.

6 . A hole transport material, comprising a central core made of tetramethyldihydrophenazine, wherein a structural formula of the hole transport material is:

wherein each of the R 1 group and the R 2 group is selected from structural formulas as follows:

7 . The hole transport material as claimed in claim 6 , wherein the hole transport material is selected from structural formulas as follows:

8 . The hole transport material as claimed in claim 6 , wherein the hole transport material is composed of tetramethyldihydrophenazine including an electron donor and an electron donor in a periphery, and a structural formula of the central core is as follows:

the electron donor is selected from

(carbazole),

(diphenylamine), and

(9,9′-dimethylacridine).

9 . An electroluminescent device, comprising: a substrate layer, a hole injection layer, a transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a translucent electrode, and an optical coupling output layer that are sequentially stacked on one another;
wherein the substrate layer comprises glass and a total reflection underlay layer including an indium tin oxide (ITO) layer, an Ag layer and an ITO layer that are stacked sequentially, and the Ag layer is a reflective surface configured to make an output light emitted from a top of the device; wherein the hole injection layer is configured to inject holes from the ITO layers into an organic light emitting diode (OLED) device, and is made of MoO 3 ; wherein the hole transport layer is configured to transport the holes injected and is capable of adjusting a resonant wavelength of a microcavity by adjusting a thickness of the hole transport layer, and the hole transport layer is made of the hole transport material as claimed in claim 6 ; wherein the electron blocking layer is configured to block and hold electrons injected into the light emitting layer in the light emitting layer to prevent the electrons from being transported to the hole transport layer, and to restrict a composite region of excitons in the light emitting layer, and the electron blocking layer is made of (4-[1-[4-[bis(4-methylphenyl)amino]phenyl]cyclohexyl]-N-(3-methylphenyl)-N-(4-methylphenyl)aniline (TAPC); wherein the light emitting layer is configured to combine the holes and the electrons to form excitons, a fluorescent material emits light by the excitons, and the light emitting layer is made of 4,4′-bis(9-carbazole)biphenyl: tris(2-phenylpyridine)iridium (Ill) doped; wherein the hole blocking layer is configured to block and hold holes injected into the light emitting layer in light emitting layer to prevent the holes from being transported to the electron transport layer, and to restrict, and to restrict a composite region of excitons in the light emitting layer, and the hole blocking layer is made of 1,3,5-Tris(3-pyridyl-3-phenyl)benzene (Tm3PyPB); wherein the electron transport layer is configured to transport the electrons injected, is made of 1,3,5-Tris(3-pyridyl-3-phenyl)benzene Tm3PyPB and 8-Hydroxyquinoline aluminum salt (LiQ), and the electron transport layer is configured

Assignees

• Wuhan China Star Optoelectronics Semiconductor Display Tech Co Ltd

Inventors

• Luo Jiajia

Classifications

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• C07D401/14 Primary

  containing three or more hetero rings · CPC title

• C07D403/14

  containing three or more hetero rings · CPC title

• C07D241/48

  with hydrocarbon radicals, substituted by nitrogen atoms, directly attached to the ring nitrogen atoms · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title