IP Library › Granted Patent US 11,683,979
Granted Patent B2
US 11,683,979 · App. 15/543,306 · Granted Jun 20, 2023

Electroactive materials

Inventors: Viacheslav V. Diev (Wilmington, DE); John David Allen (New Castle, DE); Kerwin D. Dobbs (Wilmington, DE); Weiying Gao (Landenberg, PA); Michael Henry Howard, Jr. (Montchain, DE); Michael R. Moseley (New Castle, DE); Weishi Wu (Landenberg, PA)
H01L51/0054C07C13/66C07C211/61C07D209/80C07D221/18C07D307/77C07D307/78C07D311/78C07D335/04C07D345/00C07D471/04C07D471/06C07F7/081C07F7/0816C09B57/00C09B57/001C09B57/008C09K11/06H01L51/0032H01L51/0034H01L51/0035H01L51/0043H01L51/0059H01L51/0061H01L51/0071H01L51/0072H01L51/0073H01L51/0074H01L51/0085H01L51/0094H01L51/5048H01L51/5068H01L51/5221C07C2603/54C09K2211/1011C09K2211/1025H01L51/5012
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Quick Facts
Patent No.
US 11,683,979
App. No.
15/543,306
Granted
Jun 20, 2023
Kind
B2
Abstract

There is disclosed a compound Formula I In Formula I: Z is CR 4 R 5 , C═CR 4 R 5 , SiR 4 R 5 , GeR 4 R 5 , NR 4a , PR 4a , P(O)R 4a , O, S, SO, SO 2 , Se; SeO, SeO 2 , Te, TeO, or TeO 2 ; R 1 -R 3 are the same or different at each occurrence and are D, aryl, heteroaryl, alkyl, amino, silyl, germyl, deuterated aryl, deuterated heteroaryl, deuterated alkyl, deuterated amino, deuterated silyl, or deuterated germyl, where two groups selected from R 1 , R 2 , and R 3 can be joined together to form a fused ring; R 4 -R 5 are the same or different at each occurrence and are H, D, aryl, heteroaryl, alkyl, amino, silyl, germyl, deuterated aryl, deuterated heteroaryl, deuterated alkyl, deuterated amino, deuterated silyl, or deuterated germyl; R 4a is alkyl, silyl, germyl, aryl, or a deuterated analog thereof; a is an integer from 0-4; b and c are the same or different and are an integer from 0-3.

Claims (49)

1. An electroactive material having Formula I

wherein:

Z is selected from the group consisting of C=CR 4 R 5 ,PR 4a , P(O)R 4a , Se,SeO,SeO 2 , Te, TeO and TeO 2 ;

R 1 , R 2 , and R 3 are each a hydrocarbon aryl having 6 - 36 ring carbons;

R 4 -R 5 are the same or different at each occurrence and are H, D, aryl, heteroaryl, alkyl, amino, silyl, germyl, deuterated aryl, deuterated heteroaryl, deuterated alkyl, deuterated amino, deuterated silyl, or deuterated germyl;

R 4a is selected from the group consisting of alkyl, silyl, germyl, aryl, and deuterated analogs thereof, wherein R 4 , R 5 , and R 4a do not form a fused ring with R 1 to R 3 ;

a=b=c=1.

2. An electroactive material having Formula I

wherein:

Z is selected from the group consisting of C=CR 4 R 5 , PR 4a , P(O)R 4a , S, SO, SO 2 , Se, SeO, SeO 2 , Te, TeO, and TeO 2;

R 2 and R 3 are the same or different at each occurrence and are D, aryl, heteroaryl, alkyl, amino, silyl, germyl, deuterated aryl, deuterated heteroaryl, deuterated alkyl, deuterated amino, deuterated silyl, or deuterated germyl, wherein R 2 does not form a fused ring with R 3 ;

R 4 -R 5 are the same or different at each occurrence and are H, D, aryl, heteroaryl, alkyl, amino, silyl, germyl, deuterated aryl, deuterated heteroaryl, deuterated alkyl, deuterated amino, deuterated silyl, or deuterated germyl;

R 4a is selected from the group consisting of alkyl, silyl, germyl, aryl, and deuterated analogs thereof;

a=2;

b and c are the same or different and are an integer from 0-3; and

R 1 groups at positions 1 and 2 are joined to form a 6-membered fused aromatic ring.

3. An electroactive material having Formula I

wherein:

Z is selected from the group consisting of PR 4a , P(O)R 4a , S, SO, SO 2 , Se, SeO, SeO 2 , Te, TeO, and TeO 2;

R 2 and R 3 are the same or different at each occurrence and are D, aryl, heteroaryl, alkyl, amino, silyl, germyl, deuterated aryl, deuterated heteroaryl, deuterated alkyl, deuterated amino, deuterated silyl, or deuterated germyl, wherein R 2 does not form a fused ring with R 3 ;

R 4a is selected from the group consisting of alkyl, silyl, germyl, aryl, and deuterated analogs thereof;

a=2;

b and c are the same or different and are an integer from 0-3; and

R 1 groups at positions 2 and 3 are joined to form a 6-membered fused aromatic ring.

4. An electroactive material having Formula I

wherein:

Z is selected from the group consisting of SO, SO 2 , Se, SeO, SeO 2 , Te, TeO, and TeO 2 ;

R 1 -R 3 are the same or different at each occurrence and are D, aryl, heteroaryl, alkyl, amino, silyl, germyl, deuterated aryl, deuterated heteroaryl, deuterated alkyl, deuterated amino, deuterated silyl, or deuterated germyl, where two groups selected from R 1 , R 2 and R 3 can be joined together to form a fused ring;

a=2;

b and c are the same or different and are an integer from 0-3; and

R 1 groups at positions 3 and 4 are joined to form a 6-membered fused aromatic ring.

5. An electroactive material having Formula I

wherein:

Z is selected from the group consisting of PR 4a , P(O)R 4a , Se, SeO, SeO 2 , Te, TeO, and TeO 2 ;

R 1 -R 3 are the same or different at each occurrence and are D, aryl, heteroaryl, alkyl, amino, silyl, germyl, deuterated aryl, deuterated heteroaryl, deuterated alkyl, deuterated amino, deuterated silyl, or deuterated germyl, where two groups selected from R 1 , R 2 , and R 3 can be joined together to form a fused ring;

R 4a is selected from the group consisting of alkyl, silyl, germyl, aryl, and deuterated analogs thereof;

a is an integer from 0-4;

b=2;

c is an integer from 0-3; and

R 2 groups at positions 5 and 6 are joined to form a 6-membered fused aromatic ring.

6. An electroactive material having Formula I

wherein:

Z is selected from the group consisting of PR 4a , P(O)R 4a , S, SO, SO 2 , Se, SeO, SeO 2 , Te, TeO, and TeO 2 ;

R 1 -R 3 are the same or different at each occurrence and are D, aryl, heteroaryl, alkyl, amino, silyl, germyl, deuterated aryl, deuterated heteroaryl, deuterated alkyl, deuterated amino, deuterated silyl, or deuterated germyl, where two groups selected from R 1 and R 2 can be joined together to form a fused ring;

R 4a is selected from the group consisting of alkyl, silyl, germyl, aryl, and deuterated analogs thereof, wherein R 4 a does not form a fused ring with R 1 to R 3 ;

a is an integer from 0-4;

b is an integer from 0-3;

c=2; and

R 3 groups at positions 9 and 10 are joined to form a 6-membered fused aromatic ring.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 20, 2019
From: E.I. DU PONT DE NEMOURS AND COMPANY
To: LG CHEM, LTD.
Reel/Frame 049226/0488 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 6, 2017
From: WU, WEISHI
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 044038/0086 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 31, 2017
From: DIEV, VIACHESLAV V; ALLEN, JOHN DAVID; DOBBS, KERWIN D; GAO, WEIYING; HOWARD, MICHAEL HENRY, JR.; MOSELEY, MICHAEL R.
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 043989/0531 →
Continuity (4)
Provisional Application 62111139 · Feb 3, 2015
Provisional Application 62111137 · Feb 3, 2015
Provisional Application 62111135 · Feb 3, 2015
Related Publication 20180062082A1 · Mar 1, 2018