Electroactive materials

Patent metadata

Field	Value
Publication number	US-11683979-B2
Application number	US-201615543306-A
Country	US
Kind code	B2
Filing date	Jan 20, 2016
Priority date	Feb 3, 2015
Publication date	Jun 20, 2023
Grant date	Jun 20, 2023

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.

First claim

What is claimed is:

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.

Assignees

• Lg Chemical Ltd

Inventors

• Diev Viacheslav V
• Allen John David
• Dobbs Kerwin D
• Gao Weiying
• Howard Jr Michael Henry
• Moseley Michael R
• Wu Weishi

Classifications

• H01L51/0043

  Electricity · mapped topic

• C09K2211/1025

  characterised by ligands · CPC title

• H01L51/0085

  Electricity · mapped topic

• C07F7/081

  comprising at least one atom selected from the elements N, O, halogen, S, Se or Te · CPC title

• H01L51/5068

  Electricity · mapped topic