Organic material purification composition and method of purifying organic materials using the same

Patent metadata

Field	Value
Publication number	US-10919007-B2
Application number	US-201816144302-A
Country	US
Kind code	B2
Filing date	Sep 27, 2018
Priority date	Sep 28, 2017
Publication date	Feb 16, 2021
Grant date	Feb 16, 2021

Abstract

An organic material purification composition, a mixed composition, and a method of purifying an organic material, the organic material purification composition including an ionic liquid in which a cation and an anion are combined; and an organic solvent, wherein the organic solvent includes an alcohol or a ketone.

First claim

What is claimed is:

1. An organic material purification composition, comprising: an ionic liquid in which a cation and an anion are combined; and an organic solvent, wherein the organic solvent includes an alcohol or a ketone,
wherein the alcohol includes ethanol, propanol, or butanol.

2. The organic material purification composition as claimed in claim 1 , wherein: the ketone includes acetone.

3. The organic material purification composition as claimed in claim 1 , wherein the cation of the ionic liquid is represented by one of Formulae 1-1 to 1-7 below:

wherein, in Formulae 1-1 to 1-7, R 1 to R 4 are each independently a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms.

4. The organic material purification composition as claimed in claim 3 , wherein one of R 1 to R 4 is an alkyl group having a straight chain of 12 to 20 carbon atoms.

5. The organic material purification composition as claimed in claim 1 , wherein the anion of the ionic liquid includes Cl − , Br − , NO 3 − , BF 4 − , PF 6 − , AlCl 4 − , Al 2 Cl 7 − , AcO − , CH 3 COO − , CF 3 COO − , CH 3 SO 3 − , CF 3 SO 3 − , (CF 3 SO 2 ) 2 N − , (CF 3 SO 2 ) 3 C − , (CF 3 CF 2 SO 2 ) 2 N − , C 4 F 9 SO 3 − , C 3 F 7 COO − , (CF 3 SO 2 )(CF 3 CO)N − , C 4 F 10 N − , C 2 F 6 NO 4 S 2 − , C 2 F 6 NO 6 S 2 − , C 4 F 10 NO 4 S 2 − , CF 3 SO 2 − , CF 3 SO 3 − , C 4 F 9 SO 2 − , C 4 F 9 SO 3 − , C 2 H 6 NO 4 S 2 − , C 3 F 6 NO 3 S − , (CF 3 SO 2 ) 2 N − , CH 3 CH(OH)CO 2 − , or a combination thereof.

6. The organic material purification composition as claimed in claim 1 , wherein a weight ratio of the organic solvent to the ionic liquid is from 1.0 to 5.0.

7. The organic material purification composition as claimed in claim 1 , wherein the organic material purification composition is configured to purify an organic material for a light emitting layer of an organic light emitting device.

8. A mixed composition, comprising: an ionic liquid in which a cation and an anion are combined; and an organic solvent, wherein the organic solvent includes an alcohol or a ketone, wherein the alcohol includes ethanol, propanol, or butanol, and wherein a weight ratio of the organic solvent to the ionic liquid is from 1.0 to 5.0.

9. The mixed composition as claimed in claim 8 , wherein the composition includes: 16 wt % to 50 wt % of the ionic liquid; and a balance of the organic solvent.

10. The mixed composition as claimed in claim 8 , wherein the mixed composition has a viscosity of 15 cP or less at 20° C. to 25° C.

11. The mixed composition as claimed in claim 8 , wherein: the ketone includes acetone.

12. A method of purifying an organic material, the method comprising: preparing an organic material to be purified; mixing the organic material with a mixed solution of an ionic liquid and an organic solvent, the organic solvent including an alcohol or a ketone; purifying the organic material by stirring the mixed solution in which the organic material is mixed; and separating the purified organic material,
wherein the alcohol includes ethanol, propanol, or butanol.

13. The method as claimed in claim 12 , wherein the ionic liquid includes a cation represented by one of Formulae 1-1 to 1-7 below:

wherein, in Formulae 1-1 to 1-7, R 1 to R 4 are each independently a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms.

14. The method as claimed in claim 12 , wherein the ionic liquid includes an anion, the anion including Cl − , Br − , NO 3 − , BF 4 − , PF 6 − , AlC 4 − , Al 2 Cl 4 − , AcO − , CH 3 COO − , CF 3 COO − , CH 3 SO 3 − , CF 3 SO 3 − , (CF 3 SO 2 ) 2 N − , (CF 3 SO 2 ) 3 C − , (CF 3 CF 2 SO 2 ) 2 N − , C 4 F 9 SO 3 − , C 3 F 7 COO − , (CF 3 SO 2 )(CF 3 CO)N − , C 4 F 10 N − , C 2 F 6 NO 4 S 2 − , C 2 F 6 NO 6 S 2 − , C 4 F 10 NO 4 S 2 − , CF 3 SO 2 − , CF 3 SO 3 − , C 4 F 9 SO 2 − , C 4 F 9 SO 3 − , C 2 H 6 NO 4 S 2 − , C 3 F 6 NO 3 S − , (CF 3 SO 2 ) 2 N − , CH 3 CH(OH)CO 2 − , or a combination thereof.

15. The method as claimed in claim 12 , wherein: the ketone includes acetone.

16. The method as claimed in claim 12 , wherein the mixed solution of the ionic liquid and the organic solvent includes: 16 wt % to 50 wt % of the ionic liquid; and a balance of the organic solvent.

17. The method as claimed in claim 12 , wherein the organic material is a conductive organic material for a light emitting layer of an organic light emitting device.

18. The method as claimed in claim 17 , wherein the organic material includes: a first organic material having a first polarity; and a second organic material having a second polarity that is different from the first polarity.

19. The method as claimed in claim 18 , wherein, during purifying the organic material by stirring the mixed solution in which the organic material is mixed, the first organic material is dissolved in the mixed solution, and the second organic material is not dissolved in the mixed solution.

20. The method as claimed in claim 19 , wherein separating the purified organic material includes separating the second organic material through a filter.

21. The method as claimed in claim 12 , wherein mixing the organic material with the mixed solution and purifying the organic material by stirring the mixed solution in which the organic material is mixed are performed at 20° C. to 25° C.

22. The method as claimed in claim 12 , further comprising washing and drying the separated organic material after separating the purified organic material.

23. The method as claimed in claim 12 , further comprising purifying and recycling the ionic liquid in the mixed solution from which the organic material is separated after separating the purified organic material.

24. The method as claimed in claim 12 , further comprising preparing the mixed solution by mixing and then stirring the organic solvent and the ionic liquid prior to mixing the organic material with the mixed solution.

Assignees

• Samsung Display Co Ltd
• Dms Co Ltd

Inventors

• Lee Myung-Ki
• Moon Hyunsoo
• Lee Jongwon
• Kang Sunwoo
• Park Yongseok

Classifications

• B01F23/808 Primary

  Filtering the mixture · CPC title

• B01F23/804

  Drying the mixture · CPC title

• B01F23/56

  by introducing solids in liquids, e.g. dispersing or dissolving · CPC title

• B01F23/511

  characterised by the composition of the liquids or solids · CPC title

• C09K11/02

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