IP Library Granted Patent US 10,329,483
Granted Patent B2
US 10,329,483 · App. 15/540,336 · Granted Jun 25, 2019

Fluorene derivatives as light emitting elements for electroluminescent devices

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Quick Facts
Patent No.
US 10,329,483
App. No.
15/540,336
Granted
Jun 25, 2019
Kind
B2
Abstract

The present disclosure provides a composition comprising at least one compound selected from the group consisting of Compound 1, Compound 2, and combinations thereof, as shown below, and described herein: wherein, for Compound 1 and Compound 2, independently, R 1 and R 2 each independently is selected from the group consisting of hydrogen, a substituted alkyl, an unsubstituted alkyl, a substituted heteroalkyl, an unsubstituted heteroalkyl, a substituted aryl, an unsubstituted aryl, a substituted heteroaryl and an unsubstituted heteroaryl; wherein, for Compound 1 and Compound 2, independently, the Component A is selected from the group consisting of Group a) through Group h): wherein Group a) through Group h) are described herein.

Claims (36)

1. A composition comprising at least one compound selected from the group consisting of Compound 1, Compound 2, and combinations thereof, as shown below:

wherein, for Compound 1 and Compound 2, independently, R 1 and R 2 each independently is selected from the group consisting of hydrogen, a substituted alkyl, an unsubstituted alkyl, a substituted heteroalkyl, an unsubstituted heteroalkyl, a substituted aryl, an unsubstituted aryl, a substituted heteroaryl, and an unsubstituted heteroaryl;

wherein, for Compound 1 and Compound 2, independently, the Component A is Group a):

wherein for Group a), R 3 and R 4 each independently is selected from the group consisting of hydrogen, a substituted alkyl, an unsubstituted alkyl, a substituted aryl, an unsubstituted aryl, a substituted heteroaryl, and an unsubstituted heteroaryl; and

wherein, for Compound 2, Component Z is selected from the group consisting of C(R Z ) 2 , NR Z , P(O)R Z , PR Z , S, SO, SO 2 , Si(R Z ) 2 , and O;

wherein each R Z , independently is selected from the group consisting of hydrogen, an unsubstituted alkyl, an unsubstituted aryl, and an alkoxy; and

wherein, optionally, for Compound 1 and Compound 2, independently, one or more hydrogen atoms may be substituted with deuterium.

2. The composition of claim 1 , wherein the composition comprises Compound 1, and R 1 and R 2 for Compound 1 each independently is selected from the group consisting of a substituted aryl, an unsubstituted aryl, a substituted heteroaryl, and an unsubstituted heteroaryl.

3. The composition of claim 2 , wherein the composition comprises Compound 1, and R 1 and R 2 for Compound 1 each independently is selected from the group consisting of an unsubstituted aryl and an unsubstituted heteroaryl.

4. The composition of claim 3 , wherein the composition comprises Compound 1, and

wherein for Group a), R 3 and R 4 each independently is selected from the group consisting of hydrogen, an unsubstituted aryl, and an unsubstituted heteroaryl.

5. The composition of claim 4 , wherein the composition comprises Compound 1, and Compound 1 has the Structure (i):

wherein R 1 and R 2 for Structure (i) each independently is selected from the group consisting of an unsubstituted aryl and an unsubstituted heteroaryl.

6. The composition of claim 3 , wherein the composition comprises Compound 1

wherein for Group a), R 3 and R 4 each independently is selected from hydrogen, an unsubstituted aryl, and an unsubstituted heteroaryl.

7. The composition of claim 6 , wherein the composition comprises Compound 1, and

Compound 1 has the Structure (i):

and

wherein for Structure (i), R 1 and R 2 each independently is selected from the group consisting of an unsubstituted aryl and an unsubstituted heteroaryl.

8. The composition of claim 3 , wherein the composition comprises Compound 1, and Compound 1 has a structure selected from the group consisting of Structures (ii), (iii), (iv), (v) shown below

9. The composition of claim 1 , wherein the composition comprises Compound 2, and wherein for Compound 2, R 1 and R 2 each independently is selected from the group consisting of a substituted aryl, unsubstituted aryl, a substituted heteroaryl, and an unsubstituted heteroaryl.

10. The composition of claim 9 , wherein the composition comprises Compound 2, and

wherein for Group a), R 3 and R 4 each independently is selected from the group consisting of hydrogen, an unsubstituted aryl, or an unsubstituted heteroaryl.

11. The composition of claim 10 , wherein the composition comprises Compound 2 having the Structure (viii)

and

wherein for Structure (viii), R 1 and R 2 each independently is selected from the group consisting of an unsubstituted aryl and an unsubstituted heteroaryl; and

wherein, for Structure (viii), Component Z is selected from the group consisting of CR (Z)2 , NR Z , P(O)R Z , PR Z , S, SO, SO 2 , SiR (Z)2 , and O, and wherein Rz is selected from the group consisting of hydrogen, an unsubstituted alkyl, an unsubstituted aryl, and an alkoxy.

12. The composition of claim 9 , wherein the composition comprises Compound 2

wherein for Group a), R 3 and R 4 each independently is selected from hydrogen, an unsubstituted aryl, and an unsubstituted heteroaryl.

13. The composition of claim 12 , wherein the composition comprises Compound 2, and Compound 2 has the Structure (viii):

and

wherein for Structure (viii), R 1 and R 2 each independently is selected from the group consisting of a substituted aryl, an unsubstituted aryl, a substituted heteroaryl, and an unsubstituted heteroaryl;

wherein for Structure (viii), Component Z is selected from the group consisting of CR (z)2 , NR z , P(O)R z , PR z , S, SO, SO 2 , SiR (z)2 , and O; and

wherein R z is selected from the group consisting of hydrogen, unsubstituted, alkyl, unsubstituted aryl, and an alkoxy.

14. The composition of claim 9 , wherein the composition comprises Compound 2 and Compound 2 has a structure selected from the group consisting of Structure (ix), (x), (xi), (xii), and (xiii), provided below

15. An electronic device comprising at least one component formed the composition of claim 14 .

Assignments (6)
SECURITY INTEREST Recorded Nov 3, 2025
From: QNITY ELECTRONICS, INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 073515/0243 →
SECURITY INTEREST Recorded Nov 3, 2025
From: QNITY ELECTRONICS, INC.
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS NOTES COLLATERAL AGENT
Reel/Frame 073517/0298 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 17, 2024
From: DOW GLOBAL TECHNOLOGIES LLC
To: THE DOW CHEMICAL COMPANY
Reel/Frame 068971/0226 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 17, 2024
From: THE DOW CHEMICAL COMPANY
To: DDP SPECIALTY ELECTRONIC MATERIALS US, INC
Reel/Frame 068971/0362 →
CHANGE OF LEGAL ENTITY Recorded Sep 17, 2024
From: DDP SPECIALTY ELECTRONIC MATERIALS US, INC
To: DDP SPECIALTY ELECTRONIC MATERIALS US, LLC
Reel/Frame 068972/0210 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 10, 2019
From: GRAY, KAITLYN; RACHFORD, AARON; LAITAR, DAVID; MUKHOPADHYAY, SUKRIT; FROESE, ROBERT
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 049143/0439 →