IP Library › Granted Patent US 12,364,158
Granted Patent B2
US 12,364,158 · App. 17/136,559 · Granted Jul 15, 2025

Organic electric element, display panel comprising the same and display device comprising the same

Inventors: Jicheol Shin (Gyeonggi-do, KR); Seonkeun Yoo (Gyeonggi-do, KR); Jeongdae Seo (Gyeonggi-do, KR); Shinhan Kim (Gyeonggi-do, KR); JooYong Yoon (Gyeonggi-do, KR); Jun Yun (Gyeonggi-do, KR); DongHeon Kim (Gyeonggi-do, KR); YongHan Lee (Gyeonggi-do, KR); SungJae Lee (Gyeonggi-do, KR)
Assignees: LG DISPLAY CO., LTD.; LG CHEM, LTD.
H10K85/633H10K85/6572H10K50/15H10K50/171H10K2101/30
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Quick Facts
Patent No.
US 12,364,158
App. No.
17/136,559
Granted
Jul 15, 2025
Kind
B2
Abstract

An organic electric element, a display panel, and a display device including the organic electric element are provided. The organic electric element includes a charge generating layer including a first layer comprising a first compound and a second compound and a second layer comprising a third compound so that they may have excellent efficiency or lifespan.

Claims (63)

1. An organic electric element, comprising:

a first electrode;

a second electrode; and

an organic layer positioned between the first electrode and the second electrode,

wherein the organic layer comprises:

a first stack comprising a first emitting layer,

a second stack comprising a second emitting layer, and

a charge generating layer positioned between the first stack and the second stack, the charge generating layer comprises:

a first layer, and

a second layer,

the first layer comprises:

a first compound represented by one or more of the following chemical formula 1 and chemical formula 2, and

a second compound represented by the following chemical formula 3, and

the second layer comprises a third compound represented by the following chemical formula 4:

in the chemical formula 1 and the chemical formula 2,

R 1 to R 6 , which are same or different, are each independently one selected from the group consisting of a hydrogen; a deuterium; a tritium; a halogen; a cyano group; a nitro group;

a C 6 -C 60 aryl group; a fluorenyl group; a C 2 -C 60 hetero ring group containing at least one hetero atom from O, N, S, Si and P; a fused ring group of a C 3 -C 60 aliphatic ring and a C 6 -C 60 aromatic ring; a C 1 -C 50 alkyl group; a C 2 -C 20 alkenyl group; a C 2 -C 20 alkynyl group; a C 1 -C 30 alkoxy group; a C 6 -C 30 aryloxy group; a C 3 -C 60 alkylsilyl group; a C 18 -C 60 arylsilyl group; and a C 8 -C 60 alkylarylsilyl group, and one or more of R 1 to R 6 is the cyano group,

A 1 to A 4 , which are the same or different, are each independently one selected from the group consisting of a hydrogen; a deuterium; a tritium; a halogen; a cyano group; a nitro group; a C 6 -C 60 aryl group; a fluorenyl group; a C 2 -C 60 hetero ring group containing at least one hetero atom from O, N, S, Si and P; a fused ring group of a C 3 -C 60 aliphatic ring and a C 6 -C 60 aromatic ring; a C 1 -C 50 alkyl group; a C 2 -C 20 alkenyl group; a C 2 -C 20 alkynyl group; a C 1 -C 30 alkoxy group; a C 6 -C 30 aryloxy group; a C 3 -C 60 alkylsilyl group; a C 18 -C 60 arylsilyl group; and a C 8 -C 60 alkylarylsilyl group,

in R 1 to R 6 and A 1 to A 4 of the chemical formula 1 and the chemical formula 2, the aryl group, the fluorenyl group, the hetero ring group, the fused ring group, the alkyl group, the alkenyl group, the alkynyl group, the alkoxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group and the alkylarylsilyl group are each optionally substituted with at least one substituent selected from the group consisting of a deuterium; a nitro group; a cyano group; a halogen; an amino group; a C 1 -C 20 alkoxyl group; a C 1 -C 20 alkyl group; a C 2 -C 20 alkenyl group; a C 2 -C 20 alkynyl group; a C 6 -C 20 aryl group; a C 6 -C 20 aryl group substituted with the deuterium; a fluorenyl group; a C 2 -C 20 hetero ring group; a C 3 -C 60 alkylsilyl group; a C 18 -C 60 arylsilyl group; and a C 8 -C 60 alkylarylsilyl group,

in the chemical formula 3,

R 1 and R 2 , which are the same or different, are each independently one selected from the group consisting of a C 6 -C 60 aryl group; a fluorenyl group; a C 2 -C 60 hetero ring group containing at least one hetero atom from O, N, S, Si and P; a fused ring group of a C 3 -C 60 aliphatic ring and a C 6 -C 60 aromatic ring; a C 1 -C 60 alkyl group, L is the following structure that is optionally substituted with at least one substituent selected from the group consisting of a deuterium; a nitro group; a cyano group; a halogen; an amino group; a C 1 -C 20 alkoxyl group; a C 1 -C 20 alkyl group; a C 2 -C 20 alkenyl group; a C 2 -C 20 alkynyl group; a C 6 -C 20 aryl group; a C 6 -C 20 aryl group substituted with the deuterium; a fluorenyl group; a C 2 -C 20 hetero ring group; a C 3 -C 60 alkylsilyl group; a C 18 -C 60 arylsilyl group; and a C 8 -C 60 alkylarylsilyl group:

* in the L is the position to which NR 1 R 2 is bonded,

in R 1 and R 2 of the chemical formula 3, the aryl group, the fluorenyl group, the hetero ring group, the fused ring group are each optionally substituted with at least one substituent selected from the group consisting of a deuterium; a nitro group; a cyano group; a halogen; an amino group; a C 1 -C 20 alkoxyl group; a C 1 -C 20 alkyl group; a C 2 -C 20 alkenyl group; a C 2 -C 20 alkynyl group; a C 6 -C 20 aryl group; a C 6 -C 20 aryl group substituted with the deuterium; a fluorenyl group; a C 2 -C 20 hetero ring group; a C 3 -C 60 alkylsilyl group; a C 18 -C 60 arylsilyl group; and a C 8 -C 60 alkylarylsilyl group,

in the chemical formula 4, R 1 to R 6 , which are same or different, are each independently one selected from the group consisting of a hydrogen; a deuterium; a tritium; a halogen; a cyano group; a nitro group; a C 6 -C 60 aryl group; a fluorenyl group; a C 2 -C 60 hetero ring group containing at least one hetero atom from O, N, S, Si and P; a fused ring group of a C 3 -C 60 aliphatic ring and a C 6 -C 60 aromatic ring; a C 1 -C 50 alkyl group; a C 2 -C 20 alkenyl group; a C 2 -C 20 alkynyl group; a C 1 -C 30 alkoxy group; a C 6 -C 30 aryloxy group; a C 3 -C 60 alkylsilyl group; a C 18 -C 60 arylsilyl group; and a C 8 -C 60 alkylarylsilyl group, and one or more of R 1 to R 6 is the cyano group,

Ar 1 and Ar 2 , which are same or different, are each independently one selected from the group consisting of a hydrogen; a deuterium; a tritium; a halogen; a cyano group; a nitro group; a C 6 -C 60 aryl group; a fluorenyl group; a C 2 -C 60 hetero ring group containing at least one hetero atom from O, N, S, Si and P; a fused ring group of a C 3 -C 60 aliphatic ring and a C 6 -C 60 aromatic ring; a C 1 -C 50 alkyl group; a C 2 -C 20 alkenyl group; a C 2 -C 20 alkynyl group; a C 1 -C 30 alkoxy group; a C 6 -C 30 aryloxy group; a C 3 -C 60 alkylsilyl group; a C 18 -C 60 arylsilyl group; and a C 8 -C 60 alkylarylsilyl group, and one or more of R 1 to R 6 is the cyano group, L is one selected from the group consisting of a C 6 -C 60 arylene group; a fluorylene group; a C 2 -C 60 divalent hetero ring group containing at least one heteroatom from O, N, S, Si and P; a divalent fused ring group of a C 3 -C 60 aliphatic ring and a C 6 -C 60 aromatic ring, and in R 1 to R 6 , Ar 1 , Ar 2 and L of the chemical formula 4, the aryl group, the fluorenyl group, the hetero ring group, the fused ring group, the alkyl group, the alkenyl group, the alkynyl group, the alkoxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, the alkylarylsilyl group, the arylene group, the fluorylene group, the divalent fused ring group, the divalent fused ring group are each optionally substituted with at least one substituent selected from the group consisting of a deuterium; a nitro group; a cyano group; a halogen; an amino group; a C 1 -C 20 alkoxyl group; a C 1 -C 20 alkyl group; a C 2 -C 20 alkenyl group; a C 2 -C 20 alkynyl group; a C 6 -C 20 aryl group; a C 6 -C 20 aryl group substituted with the deuterium; a fluorenyl group; a C 2 -C 20 hetero ring group; a C 3 -C 60 alkylsilyl group; a C 18 -C 60 arylsilyl group; and a C 8 -C 60 alkylarylsilyl group.

2. The organic electric element according to claim 1 , wherein the first chemical compound is represented by one or more of the following chemical formula 5 and chemical formula 6:

in the chemical formula 5 and the chemical formula 6,

n and m are each independently an integer from 0 to 5,

R 7 to R 8 , which are the same or different, are each independently one selected from the group consisting of a deuterium; a tritium; a halogen; a cyano group; a C 1 -C 50 alkyl group; and a C 1 -C 30 alkoxy group, and

in R 7 and R 8 of the chemical formula 5 and the chemical formula 6, the alkyl group and the alkoxy group are each optionally substituted with at least one substituent selected from the group consisting of a deuterium and a halogen.

3. The organic electric element according to claim 1 , wherein the first chemical compound is represented by one or more of the following chemical formula 7 and formula 8:

in the chemical formula 7 and the chemical formula 8,

R 1 to R 6 are the same as R 1 to R 6 defined in the chemical formulas 1 and 2.

4. The organic electric element according to claim 1 , wherein the first chemical compound is one or more of the following chemical compounds:

5. The organic electric element according to claim 1 , wherein the second chemical compound is one or more of the following chemical compounds:

6. The organic electric element according to claim 1 , wherein the third chemical compound is one or more of the following chemical compounds:

7. The organic electric element according to claim 1 , wherein the first electrode is an anode electrode, the second electrode is a cathode electrode, and the first layer is positioned between the second layer and the second electrode.

8. The organic electric element according to claim 1 , further comprising a hole injection layer located between the first electrode and the first light emitting layer, and

the hole injection layer comprises:

a fourth compound represented by one or more of the chemical formula 1 and the chemical formula 2, and

a fifth compound represented by the chemical formula 3.

9. The organic electric element according to claim 8 , wherein the fourth compound is the same compound as the first compound, and the fifth compound is the same organic compound as the second compound.

10. The organic electric element according to claim 1 , wherein the following general formula 1 is satisfied:

[general formula 1]

L 3 -L 1 ≤2.2 eV

In the general formula 1,

L 3 is the LUMO (Lowest Unoccupied Molecular Orbital) energy level of the third compound, and L 1 is the LUMO energy level of the first compound.

11. The organic electric element according to claim 1 , wherein the following general formula 2 is satisfied:

[general formula 2]

L 3 -H 2 ≤2.8 eV

In the general formula 2,

L 3 is the LUMO (Lowest Unoccupied Molecular Orbital) energy level of the third compound, and

H 1 is the HOMO (Highest Occupied Molecular Orbital) energy level of the second compound.

12. The organic electric element according to claim 1 , wherein the following general formula 3 is satisfied:

[general formula 3]

0.32 eV≤L 1 -H 2 ≤0.8 eV

in the general formula 3,

L 1 is the LUMO (Lowest Unoccupied Molecular Orbital) energy level of the first compound, and,

H 2 is the HOMO (Highest Occupied Molecular Orbital) energy level of the second compound.

13. A display panel comprising a subpixel comprising the organic electric element of claim 1 .

14. A display device comprising;

the display panel of claim 13 ; and

a driving circuit for driving the display panel.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 29, 2020
From: SHIN, JICHEOL; YOO, SEONKEUN; SEO, JEONGDAE; KIM, SHINHAN; YOON, JOOYONG; YUN, JUN; KIM, DONGHEON; LEE, YONGHAN; LEE, SUNGJAE
To: LG DISPLAY CO., LTD.; LG CHEM, LTD.
Reel/Frame 054767/0151 →
Continuity (1)
Related Publication 20210202845A1 · Jul 1, 2021
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