IP Library Granted Patent US 11,737,301
Granted Patent B2
US 11,737,301 · App. 17/226,158 · Granted Aug 22, 2023

Electroluminescent device, and display device comprising thereof

Inventors: Dae Young Chung (Suwon-si, KR); Moon Gyu Han (Suwon-si, KR); Oul Cho (Suwon-si, KR); Tae Hyung Kim (Seoul, KR); Sujin Park (Seoul, KR); Hongkyu Seo (Anyang-si, KR); Eun Joo Jang (Suwon-si, KR)
Assignee: SAMSUNG ELECTRONICS CO., LTD.
H10K50/19C09K11/025C09K11/06H10K50/115H10K71/00H10K71/15C09K2211/10H10K85/111H10K85/115H10K85/1135H10K85/626
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Quick Facts
Patent No.
US 11,737,301
App. No.
17/226,158
Granted
Aug 22, 2023
Kind
B2
Abstract

An electroluminescent device including a first electrode, a hole transport layer disposed on the first electrode, a first emission layer disposed on the hole transport layer, the first emission layer including a first light emitting particle on which a first ligand and a second ligand having a hole transporting property are attached, a second emission layer disposed on the first emission layer, the second emission layer including a second light emitting particle on which a first ligand and a third ligand having an electron transporting property are attached, an electron transport layer disposed on the second emission layer, and a second electrode disposed on the electron transport layer, wherein a solubility of the second ligand in a solvent is different than a solubility of the third ligand in the solvent and a display device including the same.

Claims (57)

1. An electroluminescent device, comprising

a first electrode;

a hole transport layer disposed on the first electrode;

a first emission layer disposed on the hole transport layer, the first emission layer comprising a first light emitting particle on which a first ligand and a second ligand having a hole transporting property are attached;

a second emission layer disposed on the first emission layer, the second emission layer comprising a second light emitting particle on which a first ligand and a third ligand having an electron transporting property are attached;

an electron transport layer disposed on the second emission layer; and

a second electrode disposed on the electron transport layer,

wherein a solubility of the second ligand in a solvent is different than a solubility of the third ligand in the solvent.

2. The electroluminescent device of claim 1 , wherein a hole mobility of the first emission layer is faster than a hole mobility of the second emission layer.

3. The electroluminescent device of claim 1 , wherein an electron mobility of the second emission layer is faster than an electron mobility of the first emission layer.

4. The electroluminescent device of claim 1 , wherein

when the second ligand is soluble in a hydrophilic solvent, the third ligand is soluble in a hydrophobic solvent, and

when the second ligand is soluble in a hydrophobic solvent, the third ligand is soluble in a hydrophilic solvent.

5. The electroluminescent device of claim 4 , wherein the hydrophilic solvent comprises methanol, ethanol, isopropyl alcohol, acetone, butanol, dimethyl formamide, dimethyl sulfoxide, water, acetonitrile, or a combination thereof.

6. The electroluminescent device of claim 4 , wherein the hydrophobic solvent comprises octane, heptane, nonane, hexane, xylene, toluene, chlorobenzene, chloroform, cyclohexane, or a combination thereof.

7. The electroluminescent device of claim 1 , wherein the first ligand is derived from a surfactant for attaching the first ligand represented by Chemical Formula 1:

X 1 —R 1   Chemical Formula 1

wherein, in Chemical Formula 1,

X 1 is a functional group comprising COOH, CO, CO 2 , P, POOH, P═O, PO 2 , PO 3 , S, SOOH, SO, SO 2 , SO 3 , CN, or a combination thereof, and

R 1 is a hydrocarbon group comprising a C1 to C40 substituted or unsubstituted aliphatic hydrocarbon, a C6 to C40 substituted or unsubstituted aromatic hydrocarbon, or a combination thereof.

8. The electroluminescent device of claim 7 , wherein the surfactant for attaching the first ligand is carboxylic acid compound comprising methanic acid, ethanoic acid, propanoic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, dodecanoic acid, hexadecanoic acid, octadecanoic acid, oleic acid, stearic acid, steric acid, palmitic acid, or benzoic acid; phosphonic acid compound comprising hexyl phosphonic acid, n-octyl phosphonic acid, tetradecyl phosphonic acid, or octadecyl phosphonic acid; phosphine compound comprising methyl phosphine, ethyl phosphine, propyl phosphine, butyl phosphine, pentyl phosphine, octyl phosphine, dioctyl phosphine, tributyl phosphine, trioctyl phosphine, diphenyl phosphine, or triphenyl phosphine; phosphine oxide compound comprising methyl phosphine oxide, ethyl phosphine oxide, propyl phosphine oxide, butyl phosphine oxide, pentyl phosphine oxide, tributyl phosphine oxide, octyl phosphine oxide, dioctyl phosphine oxide, or trioctyl phosphine oxide; phosphinic acid compound comprising hexylphosphinic acid, octylphosphinic acid, dodecanephosphinic acid, tetradecanephosphinic acid, hexadecanephosphinic acid, or octadecanephosphinic acid; or a combination thereof.

9. The electroluminescent device of claim 1 , the second ligand is derived from a surfactant for attaching the second ligand comprising a compound represented by Chemical Formula 2, a compound represented by Chemical Formula 3, a compound represented by Chemical Formula 4, or a combination thereof:

Y 2 —R 2   Chemical Formula 2

wherein, in Chemical Formula 2,

Y 2 is a functional group comprising SH, and

R 2 is a hydrocarbon group comprising a C1 to C40 substituted or unsubstituted aliphatic hydrocarbon, a C1 to C40 halogenated aliphatic hydrocarbon, a C6 to C40 substituted or unsubstituted aromatic hydrocarbon, a C6 to C40 halogenated aromatic hydrocarbon, or a combination thereof,

X 3 —R 3   Chemical Formula 3

wherein, in Chemical Formula 3,

X 3 is a functional group comprising N, NR′, NR′ 2 , NR′ 3 , NO, NO 2 , or a combination thereof,

R 3 is a hydrocarbon group comprising a C1 to C40 substituted or unsubstituted aliphatic hydrocarbon, a C6 to C40 substituted or unsubstituted aromatic hydrocarbon, or a combination thereof, and

R′ is a functional group comprising hydrogen, a C1 to C40 substituted or unsubstituted aliphatic hydrocarbon, a C6 to C40 substituted or unsubstituted aromatic hydrocarbon, or a combination thereof,

X 4 —R 4   Chemical Formula 4

wherein, in Chemical Formula 4,

X 4 is a functional group comprising SH, COOH, or a combination thereof, and

R 4 is a carbazole group.

10. The electroluminescent device of claim 9 , the surfactant for attaching the second ligand is methane thiol, ethane thiol, propane thiol, butane thiol, pentane thiol, hexane thiol, octane thiol, dodecane thiol, hexadecane thiol, octadecane thiol, benzyl thiol, heptyl amine, methane amine, ethane amine, propane amine, butane amine, pentyl amine, hexyl amine, octyl amine, nonyl amine, decyl amine, dodecyl amine, hexadecyl amine, octadecyl amine, dimethyl amine, diethyl amine, dipropyl amine, tributyl amine, trioctyl amine, triphenyl amine, carbazole-acid, carbazole-thiol, or a combination thereof.

11. The electroluminescent device of claim 1 , the third ligand is derived from a surfactant for attaching the third ligand represented by Chemical Formula 5:

Y 5 —R 5 —X 5   Chemical Formula 5

wherein, in Chemical Formula 5,

Y 5 is a functional group comprising SH,

R 5 is a hydrocarbon group comprising a C1 to C40 substituted or unsubstituted aliphatic hydrocarbon, a C6 to C40 substituted or unsubstituted aromatic hydrocarbon, or a combination thereof, and

X 5 is a functional group comprising OH, COOH, CO, CO 2 , P, POOH, P═O, PO 2 , PO 3 , S, SOOH, SO, SO 2 , SO 3 , or a combination thereof.

12. The electroluminescent device of claim 11 , the surfactant for attaching the third ligand is mercapto acetic acid, 3-mercapto-2-butanol, 3-mercapto-1,2-propanediol, 2-mercaptopropionic acid, 2-mercaptoethanol, methyl 3-mercaptopropionate, p-mercaptophenol, m-hydroxybenzenethiol, cyclohexyl 3-mercaptopropionate, 3-methoxybutyl mercaptoacetate, 3-methoxybutyl 3-mercaptopropionate, 6-mercapto-1-hexanol, 11-mercapto-1-undecanol, 3-mercaptopropionic acid, thioglycolic acid, cysteine, dihydrolipoic acid, 2,3-dimercapto-1-propanol, 1,2-ethanediyl bis(3-sulfanylpropanoate), pentaerythritol tetra(3-mercaptopropionate), pentaerythritol tetrathioglycolate, 2-(2-methoxyethoxy)ethanethiol, 2-(dimethylamino)ethanethiol, thiopronin, 1-thioglycerol, mercaptosuccinic acid, glutathione, or a combination thereof.

13. The electroluminescent device of claim 1 , the first light emitting particle comprises the first ligand and the second ligand in a weight ratio of about 1:0.1 to about 1:99.

14. The electroluminescent device of claim 1 , the second light emitting particle comprises the first ligand and the third ligand in a weight ratio of about 1:0.1 to about 1:99.

15. The electroluminescent device of claim 1 , wherein the first emission layer and the second emission layer emit a first light belonging to a predetermined wavelength region.

16. The electroluminescent device of claim 15 , wherein the first light belongs to a first wavelength region of about 380 nanometers to about 488 nanometers, a second wavelength region of about 490 nanometers to 510 nanometers, a third wavelength region of greater than 510 nanometers to about 580 nanometers, a fourth wavelength region of about 582 nanometers to about 600 nanometers, or a fifth wavelength region of about 620 nanometers to about 680 nanometers.

17. The electroluminescent device of claim 1 , wherein each of the first emission layer and the second emission layer has a thickness of about 10 nanometers to about 100 nanometers.

18. The electroluminescent device of claim 1 , wherein the second emission layer is disposed directly on the first emission layer.

19. A display device comprising the electroluminescent device of claim 1 .

20. A method of forming an electroluminescent device, the method comprising

disposing a hole transport layer on a first electrode;

disposing a first emission layer on the hole transport layer, the first emission layer comprising a first light emitting particle on which a first ligand and a second ligand having a hole transporting property are attached;

disposing a second emission layer on the first emission layer, the second emission layer comprising a second light emitting particle on which a first ligand and a third ligand having an electron transporting property are attached;

disposing an electron transport layer on the second emission layer; and

disposing a second electrode on the electron transport layer,

wherein a solubility of the second ligand in a solvent is different than a solubility of the third ligand in the solvent.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 9, 2021
From: CHUNG, DAE YOUNG; HAN, MOON GYU; CHO, OUL; KIM, TAE HYUNG; PARK, SUJIN; SEO, HONGKYU; JANG, EUN JOO
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 055886/0569 →
Priority Claims (2)
KR 10-2018-0031566 · Mar 19, 2018 · national
KR 10-2019-0030273 · Mar 18, 2019 · national
Continuity (2)
Continuation In Part 16356148 · Mar 18, 2019
Related Publication 20210226172A1 · Jul 22, 2021