Method of purifying light-emitting device material and light-emitting device including light-emitting device material

Patent metadata

Field	Value
Publication number	US-12069937-B2
Application number	US-202117144208-A
Country	US
Kind code	B2
Filing date	Jan 8, 2021
Priority date	Jul 10, 2020
Publication date	Aug 20, 2024
Grant date	Aug 20, 2024

Abstract

Provided is a method of purifying a phosphorescent dopant, the method including reacting the phosphorescent dopant with Ag 2 O.

First claim

What is claimed is:

1. A method of purifying a phosphorescent dopant, the method comprising reacting the phosphorescent dopant with Ag2O, wherein the phosphorescent dopant comprises an organometallic complex represented by Formula 401:
M(L 401 ) xc1 (L 402 ) xc2   Formula 401

wherein, in Formulae 401 and 402,
M is a transition metal (e.g., iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)),
L 401 is a ligand represented by Formula 402, and xc1 is 1, 2, or 3, and when xc1 is 2 or greater, at least two L 401 (s) are identical to or different from each other,
L 402 is an organic ligand, and xc2 is an integer from 0 to 4, and when xc2 is 2 or greater, at least two L 402 (s) are identical to or different from each other,
X 401 and X 402 are each independently nitrogen or carbon,
ring A 401 and ring A 402 are each independently a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,
T 401 is a single bond, —O—, —S—, —C(═O)—, —N(Q 411 )-, —C(Q 411 ) (Q 412 )-, —C(Q 411 )=C(Q 412 )-, C(Q 411 )=, or ═C(Q 411 )=,
X 403 and X 404 are each independently a chemical bond (e.g., a covalent bond or a coordinate bond), O, S, N(Q 413 ), B(Q 413 ), P(Q 413 ), C(Q 413 )(Q 414 ), or Si(Q 413 ) (Q 414 ),
Q 411 to Q 414 are each understood by referring to the description of Q 1 provided herein,
R 401 and R 402 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 20 alkyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 20 alkoxy group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , —Si(Q 401 ) (Q 402 ) (Q 403 ), —N(Q 401 ) (Q 402 ), —B(Q 401 ) (Q 402 ), —C(═O)(Q 401 ), —S(═O) 2 (Q 401 ), or —P(═O)(Q 401 ) (Q 402 ),
Q 401 to Q 403 are each understood by referring to the description of Q 1 provided herein,
xc11 and xc12 are each independently an integer from 0 to 10, and
** and *′ in Formula 402 each indicate a binding site to M in Formula 401.

2. The method of claim 1 , further comprising purifying the phosphorescent dopant by column chromatography, prior to the reacting.

3. The method of claim 1 , further comprising purifying the phosphorescent dopant by column chromatography, recrystallization, sublimation, or a combination thereof after the reacting.

4. The method of claim 1 , wherein the phosphorescent dopant is a compound comprising a transition metal and a ligand, and the ligand is an organic ligand.

5. The method of claim 4 , wherein the ligand is a monodentate ligand, a bidentate ligand, or a tetradentate ligand.

6. The method of claim 4 , wherein the transition metal is iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm).

7. The method of claim 1 , wherein the phosphorescent dopant comprises having 40 parts per million (ppm) or greater of halide impurities.

8. The method of claim 7 , wherein the halide is F—, Cl—, Br—, and/or I—.

9. The method of claim 1 , wherein the phosphorescent dopant comprises a halide as an impurity, wherein the halide is reduced to less than about 40 ppm by the reacting of the phosphorescent dopant with Ag2O.

10. The method of claim 1 , wherein the reacting of the phosphorescent dopant with Ag2O is performed in a solvent.

11. The method of claim 10 , wherein the solvent comprises an alcohol.

12. The method of claim 11 , wherein the solvent further comprises an aromatic hydrocarbon derivative, ether, a halogenated alkane, or any combination thereof.

13. The method of claim 10 , wherein the solvent comprises: a mixed solvent of an alcohol and an aromatic hydrocarbon derivative; a mixed solvent of an alcohol and ether; a mixed solvent of an alcohol and a halogenated alkane; or any combination thereof.

14. The method of claim 1 , wherein the reacting of the phosphorescent dopant with Ag2O is performed at a temperature in a range of about 0° C. to about 90° C.

15. The method of claim 1 , wherein the reacting of the phosphorescent dopant with Ag2O is performed for about 10 minutes to about 48 hours.

16. The method of claim 1 , further comprising preparation of the phosphorescent dopant by using a transition metal compound comprising at least one halide ligand prior to reacting the phosphorescent dopant with Ag2O.

17. The method of claim 1 , wherein a molar ratio of the phosphorescent dopant to Ag2O is in a range of about 1:9 to about 9:1.

18. A light-emitting device comprising the phosphorescent dopant purified according to the method of claim 1 .

19. The light-emitting device of claim 18 , further comprising an emission layer, wherein the emission layer comprises the phosphorescent dopant, and the total content of a halides as an impurity in the phosphorescent dopant in the emission layer is about 40 ppm or less.

20. An electronic apparatus comprising the light-emitting device of claim 18 .

Assignees

• Samsung Display Co Ltd

Inventors

• Lee Eunyoung
• Lee Hyunjung
• Ko Soobyung
• Kim Haejin
• Ahn Eunsoo

Classifications

• H10K71/00

  Manufacture or treatment specially adapted for the organic devices covered by this subclass · CPC title

• H10K50/818

  Reflective anodes, e.g. ITO combined with thick metallic layers · CPC title

• H10K50/18

  Carrier blocking layers · CPC title

• H10K50/16

  Electron transporting layers · CPC title

• H10K50/15

  Hole transporting layers · CPC title