# US 10,483,329 B2 · Hole transporting material, hole transporting layer, OLED display panel electronic device comprising the same

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- Number: US 10,483,329 B2
- Document ID: US10483329B2
- Status: Granted
- Kind: B2
- Application number: 15/666,923
- Filed: 2017-08-02
- Published: 2017-11-16
- Granted: 2019-11-19
- Earliest claimed: 2016-12-28
- Assignees: Shanghai Tianma Am-Oled Co., Ltd.; Tianma Micro-Electronics Co., Ltd.
- Applicants: Shanghai Tianma Am-Oled Co., Ltd.; Tianma Micro-Electronics Co., Ltd.
- Inventors: Xiangcheng Wang; Wei He; Ying Liu; Jinghua Niu; Yuji Hamada
- Web page: https://patentgrep.com/patent/US10483329B2

## CPC

- C07C 211/61: with at least one of the condensed ring systems formed by three or more rings
- H10K 59/35: comprising red-green-blue [RGB] subpixels
- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- C07C 2603/18: Fluorenes; Hydrogenated fluorenes
- H10K 50/15: Hole transporting layers
- H10K 50/16: Electron transporting layers
- H10K 50/171: {Electron injection layers}
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

The present disclosure relates to a hole transporting material having a structure of formula (I). The present disclosure provides a hole transporting material having at least one fluorenyl ring and having one non-hydrogen substituent on at least one benzene ring in the formula and being capable of obtaining a suitable mobility rate without occurrence of crosstalk between pixels. And the hole transporting material provided by the present disclosure is capable of satisfying the requirements on mask cleaning with solubility (in NMP solvent).

## Claims

### Claim 1

A hole transporting material, having a structure of formula (I),
wherein L1 is selected from the group consisting of substituted or unsubstituted fluorenylene, and substituted or unsubstituted biphenylene; wherein the two benzene rings in substituted or unsubstituted fluorenylene, are connected with the two nitrogen atoms in formula (I); wherein the two benzene rings in substituted or unsubstituted biphenylene, are connected with the two nitrogen atoms in formula (I);
L2, L3, L4 and L5 each is independently selected from the group consisting of substituted or unsubstituted fluorenyl, and substituted or unsubstituted biphenylyl; wherein L2, L3, L4 and L5 are connected with nitrogen atoms via benzene rings;
wherein L2, L3, L4 and L5 in the structure of formula (I) meet:
(1) L1 is substituted or unsubstituted fluorenylene, and/or
(2) at least one of L2, L3, L4 and L5 is substituted or unsubstituted fluorenyl;
wherein in the structure of formula (I), at least one hydrogen atom on at least one benzene ring is substituted by a non-hydrogen group, wherein the fluorenylene or fluorenyl is not deemed as being formed by substitution of at least one hydrogen atom on at least one benzene ring therein; and
wherein the hole transporting material has a hole mobility of 9×10−5-5×10−4 cm2/Vs, and a solubility of 10 g/L or more in NMP at 25° C.

### Claim 2 (depends on 1)

The hole transporting material claimed in claim 1, wherein L1 is selected from the group consisting of
or a combination of at least two said groups,
wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, and R16 each is independently selected from the group consisting of a hydrogen atom, a deuterium atom, linear chain or branched chain of alkyl groups of C1-C5, and linear chain or branched chain alkoxy group of C1-C5;
wherein L2, L3, L4 and L5 in formula (I) each is selected from the group consisting of
or a combination of at least two selected;
wherein R′1, R′2, R′3, R′4, R′5, R′6, R′7, R′8, R′9, R′10, R′11, R′12, R′13, R′14, R′15, R′16, R′17, and R′18 each is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a linear chain or a branched chain alkyl group of C1-C5, and linear chain or branched chain alkoxy group of C1-C5.

### Claim 3 (depends on 1)

The hole transporting material in claim 1, wherein L1 in formula (I) is selected from the group consisting of
L2, L3, L4 and L5 each independently is selected from the group comprising consisting of
wherein at least one fluorenyl ring exists in formula (I).

### Claim 4 (depends on 1)

The hole transporting material in claim 1, wherein L3 and L5 are the same; and L2 and L4 are the same.

### Claim 5 (depends on 1)

The hole transporting material in claim 1, which is anyone of

### Claim 6 (depends on 1)

A hole transport layer comprising the hole transporting material of claim 1, wherein the hole transport layer is doped with a p-type organic material.

### Claim 7 (depends on 6)

The hole transporting layer in claim 6, having a thickness of 600-2300 Å.

### Claim 8 (depends on 6)

The hole transporting layer in claim 6, wherein the p-type organic material has a doping density of 1 to 10 wt % in the hole transporting layer.

### Claim 9 (depends on 1)

An OLED display panel comprising a first electrode and a second electrode, wherein a laminate comprising a light emitting layer and a hole transporting layer is provided between the first electrode and the second electrode, and wherein the hole transporting layer comprises the hole transporting material of claim 1.

### Claim 10 (depends on 9)

The OLED display panel in claim 9, wherein the light emitting layer comprises at least one of a blue light emitting unit, a green light emitting unit and a red light emitting unit, or a combination of at least two of said units.

### Claim 11 (depends on 9)

The OLED display panel in claim 9, wherein the light emitting layer comprises a blue light emitting unit, a green light emitting unit and a red light emitting unit, and the blue light emitting unit, the green light emitting unit and the red light emitting unit have a common hole transporting layer comprising said hole transporting material.

### Claim 12 (depends on 11)

The OLED display panel in claim 11, wherein the common hole transporting layer has a thickness of 600-2300 Å.

### Claim 13 (depends on 10)

The OLED display panel in claim 10, wherein the green light emitting unit and the red light emitting unit comprises a phosphorescent material; and wherein the blue light emitting unit comprises a fluorescent material.

### Claim 14 (depends on 10)

The OLED display panel in claim 10, wherein a red light external quantum efficiency is 16% or more, a green light external quantum efficiency is 16% or more, and a blue light external quantum efficiency is 10% or more in the OLED display panel.

### Claim 15 (depends on 11)

The OLED display panel in claim 11, wherein the laminate further comprises at least one of a hole injection layer, an electron transporting layer, and an electron injection layer, or a combination of at least two selected therefrom.

### Claim 16 (depends on 11)

The OLED display panel in claim 11, wherein the OLED display panel comprises a first electrode, a hole injection layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injection layer, and a second electrode sequencially.

### Claim 17 (depends on 11)

The OLED display panel in claim 11, wherein the first electrode is an anode, and the second electrode is a cathode.

### Claim 18 (depends on 17)

An electronic device comprising the OLED display panel in claim 17.