IP Library Granted Patent US 9,484,539
Granted Patent B2
US 9,484,539 · App. 14/126,760 · Granted Nov 1, 2016

Polycyclic compound and organic electronic device comprising the same

Inventors: Dong Hoon Lee (Daejeon, KR); Minyoung Kang (Daejeon, KR); Jungi Jang (Daejeon, KR); Boonjae Jang (Daejeon, KR); Minseung Chun (Daejeon, KR); Kidong Koo (Daejeon, KR)
Assignee: LG Chem, Ltd.
H01L51/0058C07C255/52C07D213/57C07D217/14C07D221/12C07D307/91C07D333/76C09K11/06H01L51/0067H01L51/0072H01L51/0073H01L51/0074H05B33/10C07C2103/18C07C2103/24C07C2103/26C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1088C09K2211/1092H01L51/5076H01L51/5092Y02E10/549
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Quick Facts
Patent No.
US 9,484,539
App. No.
14/126,760
Granted
Nov 1, 2016
Kind
B2
Abstract

An exemplary embodiment of the present application provides a new compound and an organic electronic device using the same. The organic electronic device according to an exemplary embodiment of the present application shows excellent characteristics in terms of efficiency, driving voltage, and service life.

Claims (29)

1. An organic electronic device comprising:

a first electrode;

a second electrode; and

an organic material layer having one or more layers disposed between the first electrode and the second electrode,

wherein the organic material layer comprises a light emitting layer and at least one layer selected from of an electron transporting layer, an electron injection layer, and a layer which transports and injects electrons simultaneously, and

at least one of the electron transporting layer, an electron injection layer, and the layer which transports and injects electrons simultaneously comprises a compound represented by any one of the following Formulae 3 to 8:

in Formulae 3 to 8,

X 1 to X 3 are each independently O or S

R 1 and R 2 are the same as or different from each other, and are each independently a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fluorenyl group; or a substituted or unsubstituted heterocyclic group including one or more of N, O, and S atoms,

R 3 to R 10 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fluorenyl group; or a substituted or unsubstituted heterocyclic group including one or more of N, O, and S atoms,

R a , R b , R 11 , and R 12 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fluorenyl group; or a substituted or unsubstituted heterocyclic group including one or more of N, O, and S atoms, and two or more adjacent groups among R a , R b , R 11 , and R 12 are optionally bonded to each other to form a monocyclic or polycyclic ring,

R 13 to R 16 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fluorenyl group; or a substituted or unsubstituted heterocyclic group including one or more of N, O, and S atoms, and two or more adjacent groups among R 1 to R 16 , R a and R b are optionally bonded to each other to form a monocyclic or polycyclic ring,

L 1 to L 3 are each independently a direct bond; a substituted or unsubstituted arylene group; a substituted or unsubstituted alkenylene group; a substituted or unsubstituted fluorenylene group; or a substituted or unsubstituted heteroarylene group including one or more of N, O, and S atoms, and

n, m, o, p, q, and r are each independently an integer from 0 to 3.

2. The organic electronic device of claim 1 , wherein L is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted fluorenylene group; a substituted or unsubstituted pyridylene group; or a substituted or unsubstituted biphenylene group.

3. The organic electronic device of claim 1 , wherein at least one of R 1 and R 2 are each independently selected from the group consisting of the following substituted or unsubstituted structural formulae:

4. The organic electronic device of claim 1 , wherein R a and R b are the same as or different from each other, and are each independently a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted pyridyl group; a substituted or unsubstituted quinoline group; a substituted or unsubstituted phenanthrenyl group; or a substituted or unsubstituted naphthyl group, and

R a and R b are optionally bonded to each other to form a monocyclic or polycyclic ring.

5. The organic electronic device of claim 1 , wherein the compound represented by Formula 1 is any one of the following compounds in Table 1:

TABLE 1

[Compound 4-1]

[Compound 4-2]

[Compound 4-3]

[Compound 4-4]

6. The organic electronic device of claim 1 , wherein the organic electronic device is selected from the group consisting of an organic light emitting device, an organic solar cell, an organic photoconductor (OPC) drum, and an organic transistor.

7. The organic electronic device of claim 1 , wherein the organic electronic device is an organic light emitting device, and has a forward direction structure or a reverse direction structure.

8. The organic electronic device of claim 1 , wherein the organic electronic device is an organic light emitting device, and the organic material layer further comprises at least one layer selected from a hole injection layer, a hole transporting layer, and a layer which transports and injects holes simultaneously, and wherein at least one of the hole injection layer, the hole transporting layer, and the layer which transports and injects holes simultaneously comprises the compound.

9. The organic electronic device of claim 1 , wherein the organic material layer comprising the compound further includes an n-type dopant selected from the group consisting of an alkali metal, an alkali metal compound, an alkaline earth metal, an alkaline earth metal compound, and a combination thereof.

10. The organic electronic device of claim 9 , wherein the n-type dopant is included in an amount from 1% by weight to 70% by weight based on a total weight of the composition of the organic material layer comprising the compound.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 16, 2013
From: LEE, DONG HOON; KANG, MINYOUNG; JANG, JUNGI; JANG, BOONJAE; CHUN, MINSEUNG; KOO, KIDONG
To: LG CHEM, LTD.
Reel/Frame 031792/0670 →
Priority Claims (1)
KR 10-2012-0078820 · Jul 19, 2012 · national
Continuity (1)
Related Publication 20140151670A1 · Jun 5, 2014