IP Library › Granted Patent US 12,167,680
Granted Patent B2
US 12,167,680 · App. 17/137,802 · Granted Dec 10, 2024

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.
H10K85/615C07C211/61C07C255/47C07D221/20C07D471/04C09K11/06H10K85/626H10K85/633H10K85/636H10K85/654H10K85/6572C07C2603/10C07C2603/18C07C2603/97C09K2211/1007C09K2211/1011C09K2211/1018H10K50/17H10K50/19H10K85/624H10K2101/30
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Quick Facts
Patent No.
US 12,167,680
App. No.
17/137,802
Granted
Dec 10, 2024
Kind
B2
Abstract

Provided are an organic electric element, a display panel and a display device including the organic electric element which include 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 (56)

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, the organic layer comprising:

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 comprising:

a first layer comprising:

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

a second compound, and

a second layer comprising a third compound represented by chemical formula 4:

in chemical formula 1 and 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 chemical formula 1 and 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 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,

Ar 1 is 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,

Ar 2 is one selected from the group consisting of a hydrogen 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,

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 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 hetero 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, and

the second compound is one or more of:

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

in chemical formula 5 and 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 chemical formula 5 and 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 compound is represented by one or more of chemical formula 7 and formula 8:

in chemical formula 7 and chemical formula 8,

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

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

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

6. 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.

7. 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 chemical formula 1 and chemical formula 2, and

a fifth compound that is one or more of:

8. The organic electric element according to claim 7 , 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.

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

L 3 −L 1 ≤2.1 eV  [general formula 1]

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.

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

L 3 −H 2 ≤2.8 eV  [general formula 2]

in the general formula 2,

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

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

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

0.32 eV≤ L 1 −H 2 ≤0.8 eV  [general formula 3]

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.

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

13. A display device comprising;

the display panel of claim 12 ; and

a driving circuit for driving the display panel.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 30, 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 054779/0051 →
Priority Claims (1)
KR 10-2019-0179992 · Dec 31, 2019 · national
Continuity (1)
Related Publication 20210202859A1 · Jul 1, 2021