Fluorene-based compound, organic light-emitting device using same and method for preparing same

Patent metadata

Field	Value
Publication number	US-11069859-B2
Application number	US-201816337997-A
Country	US
Kind code	B2
Filing date	Jan 8, 2018
Priority date	Feb 28, 2017
Publication date	Jul 20, 2021
Grant date	Jul 20, 2021

Abstract

The present specification relates to a fluorene-based compound of Formula 1, a coating composition comprising the fluorene-based compound of Formula 1, an organic light emitting device using the same, and a manufacturing method thereof.

First claim

The invention claimed is:

1. A fluorene-based compound represented by the following Formula 1:

in Formula 1,
L1 and L2 are the same as or different from each other, and are each independently a substituted or unsubstituted alkylene group; a substituted or unsubstituted cycloalkylene group; or a substituted or unsubstituted heteroarylene group,
L is a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,
R1 to R6 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; 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, and R1 to R6 are each optionally connected to each other to form a substituted or unsubstituted hydrocarbon ring,
Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,
X1 and X2 are the same as or different from each other, and are each independently a photocurable group or a thermosetting group,
n1 and n4 are each independently an integer of 0 to 5,
n2 and n6 are each independently an integer of 0 to 4,
n3 and n5 are each independently an integer of 0 to 3,
when n1 to n6 are each 2 or more, R1s to R6s are each independently the same as or different from each other,
m1 and m2 are each independently an integer of 2 to 12, and
when m1 and m2 are each 2 or more, L1s and L2s are each independently the same as or different from each other,
wherein the photocurable group or the thermosetting group in the definitions of X1 and X2 is any one of the following structures:

in the structures,

A1 to A3 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

2. The fluorene-based compound of claim 1 , wherein L is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

3. The fluorene-based compound of claim 1 , wherein Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

4. The fluorene-based compound of claim 1 , wherein Formula 1 is represented by any one of the following Compounds 1 to 48:

5. A coating composition comprising the fluorene-based compound of claim 1 .

6. The coating composition of claim 5 , further comprising:
a p-doping material.

7. The coating composition of claim 6 , wherein the p-doping material is F4TCNQ; or a compound comprising a boron anion.

8. The coating composition of claim 5 , further comprising:
a single molecule comprising a thermosetting group or a photocurable group; or
a single molecule comprising an end group capable of forming a polymer by heat.

9. The coating composition of claim 5 , wherein the coating composition has a thin film retention rate of 95% or more in a thin film retention test, after a heat treatment at 250° C. or less.

10. An organic light emitting device comprising:
a first electrode;
a second electrode; and
an organic material layer having one or more layers provided between the first electrode and the second electrode,
wherein one or more layers of the organic material layer comprise the coating composition of claim 6 or a cured product thereof, and
the cured product of the coating composition is in a state where the coating composition is cured by a heat treatment or a light treatment.

11. The organic light emitting device of claim 10 , wherein the organic material layer comprising the coating composition or the cured product thereof is a hole transport layer, a hole injection layer, or a layer which simultaneously transports and injects holes.

12. A method for manufacturing an organic light emitting device, the method comprising:
preparing a substrate;
forming a first electrode on the substrate;
forming an organic material layer having one or more layers on the first electrode; and
forming a second electrode on the organic material layer,
wherein the forming of the organic material layer comprises forming an organic material layer having one or more layers by using the coating composition of claim 5 .

13. The method of claim 12 , wherein the forming of the organic material layer formed by using the coating composition comprises:
coating the coating composition onto the first electrode; and
subjecting the coated coating composition to a heat treatment or a light treatment.

14. The fluorene-based compound of claim 1 , wherein L is any one of the following structures:

in the structures,
X12 is S, SO, CRuRv, SiRwRx or NRy,
X1 to X11 are the same as or different from each other, and are each independently O, S, SiR′R″ or NR,
R11 to R25, Rs, Rt, Ru, Rv, Rw, Rx, Ry, R, R′, and R″ are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, and
s1 is an integer of 0 to 4.

15. The fluorene-based compound of claim 1 , wherein Ar1 and Ar2 are the same as or different from each other, and are each independently one of the following structures:

in the structures,
W is O, S, NRa, CRbRc or SiRdRe,
R31 to R41

Assignees

• Lg Chemical Ltd

Inventors

• Kang Sungkyoung
• Bae Jaesoon
• Lee Jaechol
• Yoon Seokhee
• Lee Donggu
• Kim Yongwook
• Lee Ho Gyu

Classifications

• C07C2603/94

  containing "free" spiro atoms · CPC title

• C07C2603/18

  Fluorenes; Hydrogenated fluorenes · CPC title

• H10K50/17

  Carrier injection layers · CPC title

• H10K50/15

  Hole transporting layers · CPC title

• H10K85/658

  Organoboranes · CPC title