IP Library › Granted Patent US 10,651,391
Granted Patent B2
US 10,651,391 · App. 16/384,310 · Granted May 12, 2020

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

Inventors: Jong Gwang Park (Ulsan, KR); Yun Suk Lee (Seongnam-si, KR); Ki Ho So (Cheonan-si, KR); Hyoung Keun Park (Chuncheon-si, KR); Yeon Seok Jeong (Gangwon-do, KR); Jung Hwan Park (Hwaseong-si, KR); Sun Hee Lee (Hwaseong-si, KR); Gyu Min Lee (Cheonan-si, KR)
Assignee: DUK SAN NEOLUX CO., LTD.
H01L51/0061C07D333/76C07D409/12C07D409/14C09K11/06H01L51/0074H05B33/14C09K2211/1007C09K2211/1014C09K2211/1029C09K2211/1088C09K2211/1092H01L51/0003H01L51/0005H01L51/0072H01L51/0073H01L51/0081H01L51/50H01L51/5012H01L51/5056H01L51/5064H01L51/5088Y02E10/549
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Quick Facts
Patent No.
US 10,651,391
App. No.
16/384,310
Granted
May 12, 2020
Kind
B2
Abstract

Provided is a compound for an EBL capable of improving the light emitting efficiency, stability and life span of a device, and an organic electric element and an electronic device using the same.

Claims (21)

1. A compound represented by Formula (1) below:

wherein:

1) Ar 1 , Ar 2 , Ar 3 and Ar 4 are each independently selected from the group consisting of: a halogen; a C 6 -C 60 aryl group; a fluorenyl group; a C 2 -C 60 heterocyclic group including at least one hetero atom 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 ), or may combine to form an aromatic ring or a hetero-aromatic ring by condensation of adjacent groups to a ring, wherein at least one of Ar 1 , Ar 2 , Ar 3 and Ar 4 is a substituent represented by Formula (1-1) above,

2) L 1 and L 2 are each selected from the group consisting of: a single bond; a C 6 -C 60 arylene group; a fluorenylene group; and a C 2 -C 60 hetero arylene group including at least one hetero atom of O, N, S, Si or P,

3) l is an integer of 0 to 4 and m, n and o are each an integer of 0 to 3, wherein at least one of l and o is an integer of 2 or more,

4) R 1 , R 2 , R 3 and R 4 are each independently selected from the group consisting of: hydrogen; deuterium; halogen; a C 6 -C 60 aryl group; a fluorenyl group; a C 2 -C 60 heterocyclic group including at least one hetero atom 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 alkoxy group; a C 6 -C 30 aryloxy group; and -L′-N(R a )(R b ), wherein when R 1 or R 2 is plural, a plurality of R 1 or a plurality of R 2 may combine to each other to form a ring, and wherein R 3 and/or R 4 are plural, and a plurality of R 3 and/or a plurality of R 4 combine to each other to form a ring,

5) X is O or S, and

6) In -L′-N(R a )(R b ) above, L′ 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, and R a and R b are each 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 hetero atom selected from the group consisting of O, N, S, Si, and P,

wherein, the aryl group; fluorenyl group; arylene group; heterocyclic group; fused ring group described above may be substituted by one or more of the substituent(s) selected from the group consisting of: deuterium; halogen; a silane group; a siloxan group; a 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 20 aryl group; a C 6 -C 20 aryl group substituted by deuterium; 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 and also may combine to each other to form a saturated or unsaturated ring selected from the group consisting of: an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a hetero ring having 2 to 60 carbon atoms, and a fused ring formed by the combination of them.

2. The compound according to claim 1 represented by Formula (2) or Formula (3) below:

wherein R 1 , R 2 , R 3 , R 4 , l, m, n, o, Ar 1 , Ar 2 , Ar 3 , Ar 4 , L 1 , L 2 , X are the same as defined in claim 1 .

3. The compound according to claim 1 represented by any of Formula (4) to Formula (9) below:

wherein R 1 , R 2 , R 3 , R 4 , l, m, n, o, Ar 1 , Ar 2 , Ar 3 , A 4 , L 1 , L 2 , X are the same as defined in claim 1 .

4. The compound according to claim 1 represented by any of the following compounds:

5. An organic electric element comprising: a first electrode; a second electrode; and an organic material layer positioned between the first electrode and the second electrode, wherein the organic material layer comprises one or more of the compounds according to claim 1 .

6. The organic electric element according to claim 5 , wherein the organic material layer is selected from the group consisting of a hole injection layer, a hole transport layer, an emitting-auxiliary layer, and an emitting layer, and contains one or more of the compounds.

7. The organic electric element according to claim 6 , wherein the organic material layer is a hole transport layer or an emitting-auxiliary layer.

8. The organic electric element according to claim 5 , further comprising a light efficiency enhancing layer formed on one side of the first electrode and/or on one side of the second electrode, the side being opposite to the organic material layer.

9. The organic electric element according to claim 5 , wherein the organic material layer is formed by one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, and a roll-to-roll process.

10. An electronic device comprising a display apparatus comprising the organic electric element according to claim 5 ; and a driving part configured to drive the display apparatus.

11. The electronic device according to claim 10 , wherein the organic electric element is at least one of an organic light emitting diode (OLED), an organic solar cell, an organic photo conductor, an organic transistor, and a device for monochromic or white illumination.

Priority Claims (1)
KR 10-2016-0015595 · Feb 11, 2016 · national
Continuity (2)
Continuation 15427363 · Feb 8, 2017
Related Publication 20190245148A1 · Aug 8, 2019