IP Library › Granted Patent US 10,981,876
Granted Patent B2
US 10,981,876 · App. 15/556,074 · Granted Apr 20, 2021

Spiro compound and organic light emitting element comprising same

Inventors: Yongbum Cha (Daejeon, KR); Jin Joo Kim (Daejeon, KR); Sang Duk Suh (Daejeon, KR)
C07D219/02C07D401/04C07D401/10C07D409/04C07D471/04C09K11/06H01L51/00H01L51/0052H01L51/0072H01L51/50H01L51/5056H01L51/5096
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Quick Facts
Patent No.
US 10,981,876
App. No.
15/556,074
Granted
Apr 20, 2021
Kind
B2
Abstract

The present specification provides a spiro structured compound represented by the following Chemical Formula 1 and an organic light emitting device including the same: wherein L 1 , n, Ar 1 , R 1 to R 7 , p, q, r, s, and t are defined herein.

Claims (48)

1. A compound represented by the following Chemical Formula 2:

in Chemical Formula 2,

L 1 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene; n is an integer of 0 to 2, and when n is 2, each L 1 is the same as or different from each other;

Ar 1 is a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamino group; a substituted or unsubstituted arylphosphine group; or a substituted or unsubstituted silyl group; and

R 5 to R 7 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 hydroxy group; a carbonyl group; an ester group; an imide group; an amino group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aralkyl group; a substituted or unsubstituted aralkenyl group; a substituted or unsubstituted alkylaryl group; a substituted or unsubstituted alkylamino group; a substituted or unsubstituted aralkylamino group; a substituted or unsubstituted heteroarylamino group; a substituted or unsubstituted arylamino group; a substituted or unsubstituted arylheteroarylamino group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group; and

each of Ar 1 , R 5 and R 6 optionally combines with an adjacent group via a single bond to form a ring, R 7 does not combine with an adjacent group via a single bond to form a ring s, and r are each independently an integer of 0 to 4, t is an integer of 0 to 3, and when r, s, and t are each 2 or more, each of R 5 , R 6 and R 7 , respectively, is the same as or different from each other,

R 8 and R 9 are hydrogen, and u=4, and v=5.

2. The compound of claim 1 , wherein R 5 to R 7 are the same as or different from each other, and are each independently hydrogen; or deuterium.

3. The compound of claim 1 , wherein Ar 1 is an aryl group which is unsubstituted or substituted with one or two or more groups of a halogen group, a nitrile group, an alkyl group, a silyl group, an arylamino group, an arylphosphine group, an aryl group, and a heteroaryl group; a heterocyclic group which is unsubstituted or substituted with one or two or more groups of a halogen group, a nitrile group, an alkyl group, a silyl group, an arylamino group, an arylphosphine group, an aryl group, and a heteroaryl group; an arylamino group which is unsubstituted or substituted with one or two or more groups of a halogen group, a nitrile group, an alkyl group, a silyl group, an arylamino group, an arylphosphine group, an aryl group, and a heteroaryl group; an arylphosphine group which is unsubstituted or substituted with one or two or more groups of a halogen group, a nitrile group, an alkyl group, a silyl group, an arylamino group, an arylphosphine group, an aryl group, and a heteroaryl group; a trialkylsilyl group; or a triarylsilyl group.

4. The compound of claim 1 , wherein L 1 is a direct bond or a substituted or unsubstituted arylene.

5. The compound of claim 1 , wherein L 1 is a direct bond, phenylene, biphenylylene, terphenylylene, quarterphenylylene, naphthylene, anthrylene, fluorene, phenanthrene, pyrene, or triphenylene.

6. The compound of claim 1 , wherein the compound of Chemical Formula 2 is any one selected from the following structural formulae:

7. An organic light emitting device comprising:

a first electrode;

a second electrode provided to face the first electrode; and

one or more organic material layers provided between the first electrode and the second electrode,

wherein the one or more organic material layers comprise the compound of claim 1 .

8. The organic light emitting device of claim 7 , wherein the one or more organic material layers comprises a hole transport layer, and the hole transport layer comprises the compound.

9. The organic light emitting device of claim 7 , wherein the one or more organic material layers comprises a hole injection layer, and the hole injection layer comprises the compound.

10. The organic light emitting device of claim 7 , wherein the one or more organic material layers comprises an electron blocking layer, and the electron blocking layer comprises the compound.

11. The organic light emitting device of claim 7 , wherein the one or more organic material layers comprises a layer which injects and transports holes simultaneously, and the layer which injects and transports holes simultaneously comprises the compound.

12. The organic light emitting device of claim 7 , wherein the one or more organic material layers comprises a compound represented by the following Chemical Formula 1-A:

in Chemical Formula 1-A,

n1 is an integer of 1 or more,

Ar7 is a substituted or unsubstituted monovalent or more benzofluorene group; a substituted or unsubstituted monovalent or more fluoranthene group; a substituted or unsubstituted monovalent or more pyrene group; or a substituted or unsubstituted monovalent or more chrysene group,

L4 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

Ar8 and Ar9 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted germanium group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted arylalkyl group; or a substituted or unsubstituted heteroaryl group; and Ar8 and Ar9 optionally combine with each other via a single bond to form a substituted or unsubstituted ring, and

when n1 is 2 or more, each of L4, Ar8 and Ar9, respectively, is the same as or different from each other.

13. The organic light emitting device of claim 12 , wherein L4 is a direct bond, Ar7 is a divalent pyrene group, Ar8 and Ar9 are the same as or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms, which is unsubstituted or substituted with an alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and n1 is 2.

14. The organic light emitting device of claim 7 , wherein the one or more organic material layers comprises a compound represented by the following Chemical Formula 2-A:

in Chemical Formula 2-A,

G11 is a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group, a 3-phenanthryl group, a 4-phenanthryl group, a 9-phenanthryl group, a 1-naphthacenyl group, a 2-naphthacenyl group, a 9-naphthacenyl group, a 1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenyl group, a 3-methyl-2-naphthyl group, a 4-methyl-1-naphthyl group, or the following Chemical Formula

G12 is a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2 anthryl group, a 9-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group, a 3-phenanthryl group, a 4-phenanthryl group, a 9-phenanthryl group, a 1-naphthacenyl group, a 2-naphthacenyl group, a 9-naphthacenyl group, a 1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenyl group, a 2-biphenylyl group, a 3-biphenylyl group, a 4-biphenylyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a p-t-butylphenyl group, a p-(2-phenylpropyl)phenyl group, a 3-methyl-2-naphthyl group, a 4-methyl-1-naphthyl group, a 4-methyl-1-anthryl group, a 4-methylbiphenylyl group, a 4″-t-butyl-p-terphenyl-4-yl group, or a 3-fluoranthenyl group,

G13 and G14 are the same as or different from each other, and are each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

g12 is an integer of 1 to 5,

g13 and g14 are each independently an integer of 1 to 4, and

when g12 to g14 are each 2 or more, each of G12, G13 and G14, respectively, is the same as or different from each other.

15. The organic light emitting device of claim 14 , wherein G11 is a 1-naphthyl group, and G12 is a 2-naphthyl group.

16. The organic light emitting device of claim 12 , wherein the one or more organic material layers comprises a compound represented by the following Chemical Formula 2-A:

in Chemical Formula 2-A,

G11 is a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group, a 3-phenanthryl group, a 4-phenanthryl group, a 9-phenanthryl group, a 1-naphthacenyl group, a 2-naphthacenyl group, a 9-naphthacenyl group, a 1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenyl group, a 3-methyl-2-naphthyl group, a 4-methyl-1-naphthyl group, or the following Chemical Formula

G12 is a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group, a 3-phenanthryl group, a 4-phenanthryl group, a 9-phenanthryl group, a 1-naphthacenyl group, a 2-naphthacenyl group, a 9-naphthacenyl group, a 1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenyl group, a 2-biphenylyl group, a 3-biphenylyl group, a 4-biphenylyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a p-t-butylphenyl group, a p-(2-phenylpropyl)phenyl group, a 3-methyl-2-naphthyl group, a 4-methyl-1-naphthyl group, a 4-methyl-1-anthryl group, a 4-methylbiphenylyl group, a 4″-t-butyl-p-terphenyl-4-yl group, or a 3-fluoranthenyl group,

G13 and G14 are the same as or different from each other, and are each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

g12 is an integer of 1 to 5,

g13 and g14 are each independently an integer of 1 to 4, and

when g12 to g14 are each 2 or more, each of G12, G13 and G14, respectively, is the same as or different from each other.

17. A display device comprising the organic light emitting device of claim 1 .

18. A lighting device comprising the organic light emitting device of claim 1 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 7, 2017
From: CHA, YONGBUM; KIM, JIN JOO; SUH, SANG DUK
To: LG CHEM, LTD.
Reel/Frame 043522/0808 →
Priority Claims (1)
KR 10-2015-0138092 · Sep 30, 2015 · national
Continuity (1)
Related Publication 20180265477A1 · Sep 20, 2018
Cited By (1)
US 12,588,409