IP Library › Granted Patent US 11,355,734
Granted Patent B2
US 11,355,734 · App. 16/779,719 · Granted Jun 7, 2022

Organic photoelectronic element comprising fluorinated polymer

Inventors: Takefumi Abe (Chiyoda-ku, JP); Yasuhiro Kuwana (Chiyoda-ku, JP); Shigeki Hattori (Chiyoda-ku, JP); Kaori Tsuruoka (Chiyoda-ku, JP); Daisuke Yokoyama (Yonezawa, JP)
Assignees: AGC Inc.; National University Corporation Yamagata University
H01L51/5265H01L51/004H01L51/5004H01L51/5056H01L51/5072H01L51/5088H01L51/5092H01L51/001
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Quick Facts
Patent No.
US 11,355,734
App. No.
16/779,719
Granted
Jun 7, 2022
Kind
B2
Abstract

To provide an organic photoelectronic element, of which the external quantum efficiency is improved, the power consumption is low and the service life is prolonged. The organic photoelectronic element comprises a substrate, an anode provided on the substrate, a cathode facing the anode, a light emitting layer disposed between the anode and the cathode, and a hole transport layer provided in contact with the light emitting layer between the light emitting layer and the anode, wherein the hole transport layer contains an organic semiconductor material and a fluorinated polymer, and at the surface of the hole transport layer in contact with the light emitting layer, the fluorinated polymer is present.

Claims (22)

1. An organic photoelectronic element comprising

a substrate,

an anode provided on the substrate,

a cathode facing the anode,

a light emitting layer disposed between the anode and the cathode,

a hole transport layer provided in contact with the light emitting layer between the light emitting layer and the anode, wherein

the hole transport layer contains an organic semiconductor material and a fluorinated polymer, and

at the surface of the hole transport layer in contact with the light emitting layer, the fluorinated polymer is present;

wherein the fluorinated polymer is (i) a polymer which does not have an aliphatic ring and has units derived from a fluoroolefin, or (ii) a polymer which has an aliphatic ring structure in the main chain, and wherein the fluorinated polymer has an evaporation rate of at least 0.01 g/m 2 sec at 300° C. in a vacuum degree of 1×10 −3 Pa;

wherein the fluorinated polymer does not comprise vinylidene fluoride units.

2. The organic photoelectronic element according to claim 1 , which further has a hole injection layer which is disposed between the hole transport layer and the anode and which contains a semiconductor material and a fluorinated polymer.

3. The organic photoelectronic element according to claim 1 , wherein in the hole transport layer, the refractive index is continuously increasing toward the anode from the light emitting layer.

4. The organic photoelectronic element according to claim 1 , which further has a functional layer disposed between the cathode and the light emitting layer, wherein the functional layer has at least one of an electron transport layer and an electron injection layer, and contains a semiconductor material and a fluorinated polymer.

5. The organic photoelectronic element according to claim 1 , wherein the refractive index in the wavelength range of from 450 nm to 800 nm, of the hole transport layer provided in contact with the light emitting layer, is at most 1.60.

6. The organic photoelectronic element according to claim 1 , wherein the volume ratio of the content (A) of the fluorinated polymer to the content (B) of the organic semiconductor material in the hole transport layer is (A):(B)=from 70:30 to 5:95.

7. The organic photoelectronic element according to claim 1 , wherein the refractive index in the wavelength range of from 450 nm to 800 nm, of the fluorinated polymer, is at most 1.5.

8. The organic photoelectronic element according to claim 1 , wherein the fluorinated polymer is a perfluoropolymer having an aliphatic ring structure in the main chain.

9. The organic photoelectronic element according to claim 8 , wherein the perfluoropolymer is polyperfluoro(3-butenyl vinyl ether).

10. The organic photoelectronic element according to claim 9 , wherein the intrinsic viscosity of the polyperfluoro(3-butenyl vinyl ether) is from 0.01 to 0.14 dl/g.

11. The organic photoelectronic element according to claim 1 , wherein the weight average molecular weight of the fluorinated polymer is from 1,500 to 50,000.

12. The organic photoelectronic element according to claim 1 , wherein the organic photoelectronic element is an organic EL element.

13. The organic photoelectronic element according to claim 1 , wherein the fluorinated polymer has a glass transition temperature (Tg) of at least 60° C.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 3, 2020
From: ABE, TAKEFUMI; KUWANA, YASUHIRO; HATTORI, SHIGEKI; TSURUOKA, KAORI; YOKOYAMA, DAISUKE
To: AGC INC.; NATIONAL UNIVERSITY CORPORATION YAMAGATA UNIVERSITY
Reel/Frame 051777/0830 →
Priority Claims (1)
JP JP2017-161642 · Aug 24, 2017 · national
Continuity (2)
Continuation PCTJP2018031241 · Aug 23, 2018
Related Publication 20200176715A1 · Jun 4, 2020
Cited By (2)
US 12,672,476 US 12,740,286