Method of manufacturing organic optoelectronic device, and organic optoelectronic device and display device

Patent metadata

Field	Value
Publication number	US-12414461-B2
Application number	US-202117163861-A
Country	US
Kind code	B2
Filing date	Feb 1, 2021
Priority date	Oct 11, 2013
Publication date	Sep 9, 2025
Grant date	Sep 9, 2025

Abstract

Disclosed are an organic alloy for an organic optoelectric device that is an organic alloy of at least two kinds of organic compounds, the at least two kinds of organic compounds includes a first organic compound and a second organic compound, a difference between evaporation temperatures of the first organic compound and the second organic compound is less than or equal to about 20° C. at less than or equal to about 10 −3 torr, and a light emitting wavelength of the organic alloy is different from light emitting wavelengths of the first organic compound, the second organic compound, and a simple mixture of the first organic compound and the second organic compound, and an organic optoelectric device and a display device including the organic alloy.

First claim

The invention claimed is:

1. A method of manufacturing an organic light emitting device, the method comprising:
providing an anode and a cathode, and forming an organic layer between the anode and the cathode, wherein the forming the organic layer includes:
(a) heat-treating a first organic host compound and a second organic host compound together, and solidifying the heat-treated first and second organic host compounds through cooling to obtain a solidified host organic material, and
(b) dry coating the solidified organic host material and a dopant to form the organic layer, the dry coating including one or more of evaporation, sputtering, plasma plating, and ion plating,
wherein:
the heat-treating of (a) is performed by subliming the first organic host compound and the second organic host compound, and
a difference between evaporation temperatures of the first organic host compound and the second organic host compound is less than or equal to 20° C. as determined at a same pressure at less than or equal to 10 −3 torr, wherein the evaporation temperatures of the respective first and second organic host compounds are determined as a temperature at which the respective one of the first and second organic host compounds deposits on a substrate at a rate of rate of about 0.5 to about 2 Å/sec under a vacuum of less than or equal to about 10 −3 Torr.

2. The method of claim 1 , wherein a maximum light emitting wavelength of the solidified organic host material is different from maximum light emitting wavelengths of the first organic host compound, the second organic host compound, and an untreated mixture of the first organic host compound and the second organic host compound, the maximum light emitting wavelengths being determined at a same condition.

3. The method of claim 1 , further comprising: grinding the solidified organic host material to form a powdered organic host material, wherein the dry coating is performed using the powdered organic host material.

4. The method of claim 1 , wherein the first organic host compound and the second organic host compound are included in a mole ratio of 1:10 to 10:1.

5. The method of claim 1 , wherein the first organic host compound and the second organic host compound are included in a mole ratio of 1:1.

6. The method of claim 1 , wherein the difference between evaporation temperatures of the first organic host compound and the second organic host compound is 0° C. to 10° C. as determined at a same pressure at less than or equal to 10 −3 torr.

7. The method of claim 2 , wherein the maximum light emitting wavelength of the solidified organic host material is shifted greater than or equal to 20 nm compared with the maximum light emitting wavelength of the untreated mixture of the first organic host compound and the second organic host compound.

8. The method of claim 2 , wherein the solidified organic host material has a color with a longer wavelength region than wavelength regions of the first organic host compound, the second organic host compound, and the untreated mixture of the first organic host compound and the second organic host compound.

9. The method of claim 2 , wherein the solidified organic host material has a different melting point (Tm) than melting points of the first organic host compound, the second organic host compound, and the untreated mixture of the first organic host compound and the second organic host compound.

10. The method of claim 9 , wherein the solidified organic host material has a constant melting point (Tm).

11. The method of claim 1 , wherein the solidified organic host material is present as a solid at room temperature.

12. The method of claim 1 , wherein (a) is performed by:
putting the first organic host compound and the second organic host compound in a mole ratio of 1:1 in a vacuum chamber at less than or equal to 10 −3 Torr;
subliming the first organic host compound and the second organic host compound by increasing temperature of the vacuum chamber; and
solidifying the sublimed first and second organic host compounds through cooling to a temperature of 25° C. to yield the solidified organic host material.

13. The method of claim 1 , wherein the organic layer includes an emission layer, and the emission layer includes the dry coated organic host material.

14. The method of claim 1 , wherein the first organic host compound has electron characteristics, and the second organic host compound has hole characteristics.

15. The method of claim 1 , wherein:
the first organic host compound is represented by Chemical Formula 1 , and the second organic host compound is represented by Chemical Formula 2 ,

wherein, in Chemical Formula 1,
Z is independently N or CR a ,
at least one of Z is N,
R 1 to R 10 and R a are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a combination thereof,
L is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group or a substituted or unsubstituted terphenylene group,
n1 to n3 are independently 0 or 1, and
n1+n2+n3≥1,

wherein, in Chemical Formula 2,
Y 1 and Y 2 are independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
Ar 1 and Ar 2 are independently substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, and
R 11 to R 13 and R 43 to R 44 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heterocyclic group, or a combination thereof.

16. The method of claim 15 , wherein:
the first organic host compound is selected from Group A, and
the second organic host compound is selected from Group B,

17. An organic light emitting device manufactured by the method of claim 1 .

18. A display device comprising the organic light emitting device of claim 17 .

19. A method of manufacturing an organic light emitting device, the method comprising:
providing an anode and a cathode, and forming an organic layer between the anode and the cathode, wherein the forming the organic layer includes:
(a) heat-treating a first organic host compound and a second organic host compound together, and solidifying the heat-treated first and second organic host compounds through cooling to obtain a solidified organic host material, and
(b) dry coating the solidified organic host material and a dopant to form the organic layer, the dry coating including one or more of evaporation, sputtering, plasma plating, and ion plating,
wherein:
the heat-treating of (a) is performed by subliming the first organic host compound and the second organic host compound,
the first organic host compound is selected from Gr

Assignees

• Samsung Sdi Co Ltd

Inventors

• Park Sun-Ha
• Kang Gi-Wook
• Kang Eui-Su
• Kim Hun
• Oh Jae-Jin
• Ryu Dong-Kyu
• Lee Sang-Shin
• Lee Han-Ill
• Min Soo-Hyun
• Park Min-Jee
• Yu Eun-Sun

Classifications

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K11/02

  Use of particular materials as binders, particle coatings or suspension media therefor · CPC title

• C23C14/02

  Pretreatment of the material to be coated (C23C14/04 takes precedence) · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title