IP Library › Granted Patent US 10,991,888
Granted Patent B2
US 10,991,888 · App. 15/999,002 · Granted Apr 27, 2021

Compound for organic electronic element, organic electronic element using the same, and an electronic device

Inventors: Bum Sung Lee (Cheonan-si, KR); Sun Hee Lee (Cheonan-si, KR); Soung Yun Mun (Cheonan-si, KR); Jung Cheol Park (Suwon-si, KR); Hak Young Lee (Cheonan-si, KR)
Assignee: DUK SAN NEOLUX CO., LTD.
H01L51/0061C07C211/54C07C211/58C07C211/61C07D209/82C07D209/86C07D333/76C09K11/06H01L51/006H01L51/0058H01L51/0059H01L51/0072H01L51/0074H01L51/50H05B33/20C07C2603/97C09K2211/1007C09K2211/1014C09K2211/1022C09K2211/1092H01L51/0052H01L51/0056H01L51/5012H01L51/5056Y02E10/549
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Quick Facts
Patent No.
US 10,991,888
App. No.
15/999,002
Granted
Apr 27, 2021
Kind
B2
Abstract

Provided is an organic electronic element comprising a hole transport layer containing a compound of Formula (1) and an emitting auxiliary layer containing a compound of Formula (2), capable of improving the light emitting efficiency, stability, and life span of an electronic device using the same.

Claims (26)

1. An organic electronic element comprising:

a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, wherein the organic material layer includes an emitting auxiliary layer formed between the first electrode and the emitting layer, and a hole transport layer formed between the first electrode and the emitting auxiliary layer, wherein the hole transport layer contains a compound represented by the following Formula (1), and the emitting auxiliary layer contains a compound represented by the following Formula (2),

in Formulas (1) and (2), Ar 1 , Ar 2 , Ar 4 , Ar 5 and Ar 6 are each independently selected from the group consisting of a C 6 -C 60 aryl group; a fluorenyl group; a C 2 -C 60 heterocyclic group including at least one heteroatom of O, N, S, Si or 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 aklenyl group; a C 2 -C 20 alkynyl group; a C 1 -C 30 alkoxyl group; a C 6 -C 30 aryloxy group; and -L′-N(R a )(R b ) (where, L′ may be selected from the group consisting of a single bond; a C 6 -C 60 arylene group; a fluorenylene group; a fused ring group of a C 3 -C 60 aliphatic ring and a C 6 -C 60 aromatic ring; and a C 2 -C 60 heterocyclic, and the R a and R b may be independently selected from the group consisting of a C 6 -C 60 aryl group, a fluorenyl group, a fused ring group of a C 3 -C 60 aliphatic ring and a C 6 -C 60 aromatic ring; and a C 2 -C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si, or P), and

Ar 3 is at least one of the Formula (1-a) or Formula (1-b) below,

wherein q, r and s are each an integer of 0 to 4, t is an integer of 0 to 3, and R 1 , R 2 , R 3 , R 4 are the same or different, and are each independently selected from the group consisting of deuterium; halogen; a C 6 -C 60 aryl group; a fluorenyl group; a C 2 -C 60 heterocyclic group including at least one heteroatom of O, N, S, Si or 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 alkoxyl group; a C 6 -C 30 aryloxy group; and -L′-N(R a )(R b ) (wherein, L′, R a and R b are the same as indicated above), wherein in case q, r and s are each an integer of 2 or more, R 1 , R 2 and R 3 are each in plural and are the same or different, and a plurality of R 1 or a plurality of R 2 or a plurality of R 3 or a plurality of R 4 may combine to each other to form a ring, and

L 4 is selected from the group consisting of a C 6 -C 60 arylene group, and a fluorenylene group; a fused ring group of a C 3 -C 60 aliphatic ring and a C 6 -C 60 aromatic ring; and a C 2 -C 60 heterocyclic group including at least one heteroatom of O, N, S, Si or P, and

L 5 is selected from the group consisting of a single bond; a C 6 -C 60 arylene group; a fluorenylene group; a fused ring group of a C 3 -C 60 aliphatic ring and a C 6 -C 60 aromatic ring; and a C 2 -C 60 heterocyclic group including at least one heteroatom of O, N, S, Si or P, and

Ar 7 is independently selected from the group consisting of a C 6 -C 60 aryl group; a fluorenyl group; a C 2 -C 60 heterocyclic group including at least one heteroatom of O, N, S, Si or 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 alkoxyl group; a C 6 -C 30 aryloxy group; and -L′-N(R a )(R b ) (wherein, L′, R a and R b are as defined above), and

L 1 , L 2 and L 3 are selected from the group consisting of a single bond; a C 6 -C 60 arylene group; a fluorenylene group; a fused ring group of a C 3 -C 60 aliphatic ring and a C 6 -C 60 aromatic ring; a C 2 -C 60 heterocyclic group including at least one heteroatom of O, N, S, Si or P,

wherein the aryl group, fluorenyl group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxyl group, aryloxy group, arylene group and fluorenylene group may be substituted with one or more substituents selected from the group consisting of deuterium; halogen; a silane group; a siloxane group; boron group; a germanium group; a cyano group; a nitro group; -L′-N(R a )(R b ); a C 1 -C 20 alkylthio 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 60 aryl group; a C 6 -C 60 aryl group substituted with deuterium; a fluorenyl group; a C 2 -C 20 heterocyclic group; a C 3 -C 20 cycloalkyl group; a C 7 -C 20 arylalkyl group; and a C 8 -C 20 arylalkenyl group, wherein the substituents may combine each other to form a saturated or unsaturated ring selected from the group consisting of a C 3 -C 60 aliphatic ring, a C 6 -C 60 aromatic ring, a C 2 -C 60 heterocyclic ring, and a fused ring formed by the combination thereof.

2. The organic electronic element according to claim 1 , wherein the compound represented by the Formula (1) is one of compounds of the following Formulas (3) to (4),

in Formula (3) and Formula (4), R 1 , R 2 , R 3 , R 4 , L 4 , L 5 , Ar 1 , Ar 2 , Ar 7 , q, r, s, and t are the same as defined in claim 1 .

3. The organic electronic element according to claim 1 , wherein the compound represented by the Formula (1) is one of compounds represented by the following of Formula (5) to Formula (7),

in Formula (5), Formula (6) and Formula (7), R 3 , R 4 , Ar 1 , Ar 2 , Ar 7 , s, and t are the same as defined in claim 1 .

4. The organic electronic element according to claim 1 , wherein the compound represented by the Formula (2) of the emission-auxiliary layer is one of compounds of Formula (8) to Formula (12) below,

in Formula (8), Formula (9), Formula (10), Formula (11) and Formula (12), L 1 , L 2 , L 3 , Ar 4 , Ar 5 , and Ar 6 are the same as defined in claim 1 .

5. The organic electronic element according to claim 1 , wherein L 1 , L 2 , L 3 , and L 5 in the compounds represented by the Formula (1) and the Formula (2) are a single bond, or L 1 , L 2 , L 3 , L 4 and L 5 are represented by the following Formulas,

6. The organic electronic element according to claim 2 , wherein the compounds represented by the formula (1) of the hole transport layer or by the Formulas (3) to (7) are one of the following compounds,

7. The organic electronic element according to claim 4 , wherein the compounds represented by the formula (2) of the emitting-auxiliary layer or by the formulas (8) to (12) are one of the following compounds,

8. The organic electronic element according to claim 1 , wherein all of Ar 4 to Ar 6 in the formula (2) are aryl groups of C 6 to C 60 .

9. The organic electronic element according to claim 1 , wherein at least one of Ar 4 to Ar 6 of the Formula (2) is an C 6 -C 60 heteroaryl group.

10. The organic electronic element according to claim 2 , wherein the hole transport layer comprises a compound represented by Formula (3) and the emitting auxiliary layer comprises a compound represented by Formula (2).

11. The organic electronic element according to claim 2 , wherein the hole transport layer comprises a compound represented by Formula (4) and the emitting auxiliary layer comprises a compound represented by Formula (2).

12. The organic electronic element according to claim 1 , wherein the emitting auxiliary layer comprises a mixture of two or more compounds represented by the formula (2).

13. A display device comprising the organic electronic element of claim 2 ; and a control part driving the display apparatus.

14. The display device according to claim 13 , wherein the organic electronic element is at least one of an OLED, an organic solar cell, an organic photo conductor (OPC), Organic transistor (organic TFT) and an element for monochromic or white illumination.

Priority Claims (1)
KR 10-2014-0113885 · Aug 29, 2014 · national
Continuity (2)
Continuation 15507046
Related Publication 20190006597A1 · Jan 3, 2019
Cited By (1)
US 12,559,500