High energy triarylamine compounds for hole transport materials

Patent metadata

Field	Value
Publication number	US-2016285000-A1
Application number	US-201615074728-A
Country	US
Kind code	A1
Filing date	Mar 18, 2016
Priority date	Mar 25, 2015
Publication date	Sep 29, 2016
Grant date	—

Abstract

This invention relates to triarylamine compounds and compositions including such compounds, that are useful in electronic applications. It also relates to electronic devices in which the active layer includes such a compound or composition. The triarylamine compound can be present as a hole transport material in a hole transport layer. The triarylamine compound can also be present in a photoactive layer in combination with an organometallic compound capable of electroluminescence having an emission maximum between 380 and 750 nm.

First claim

What is claimed is:

1 . A triarylamine having Formula I, Formula IA, Formula IIA, Formula IIB, Formula III, Formula IIIA, or Formula IV

where:
E is the same or different at each occurrence and is selected from the group consisting of (CR′ 2 ) X , O, (SiR′ 2 ) X , (GeR′ 2 ) X , S, and Se;
E 1 =Si, Ge, PO, SiR′, or GeR′;
R is the same or different at each occurrence and is selected from the group consisting of D, alkyl, silyl, germyl, aryl, deuterated alkyl, deuterated silyl, deuterated germyl, and deuterated aryl, where two adjacent R groups can be joined together to form a cycloaliphatic ring, an aromatic ring, or deuterated analog thereof;
R′ is the same or different at each occurrence and is selected from the group consisting of H, D, alkyl, silyl, germyl, aryl, deuterated alkyl, deuterated silyl, deuterated germyl, and deuterated aryl, where two adjacent R′ groups can be joined together to form a cycloaliphatic ring or deuterated cycloaliphatic ring;
R1-R6 are the same or different and are selected from the group consisting of H, D, C1-8 alkyl, and deuterated C1-8 alkyl;
L is the same or different at each occurrence and is selected from the group consisting of H, D, halogen, alkyl, aryl, crosslinkable groups, deuterated alkyl, deuterated aryl, and deuterated crosslinkable groups;
L 1 is the same or different at each occurrence and is selected from the group consisting of H, D, halogen, aryl, arylamino, crosslinkable groups, deuterated aryl, deuterated arylamino, and deuterated crosslinkable groups;
Ar 1 and Ar 2 are the same or different and are selected from the group consisting of aryl groups and deuterated analogs thereof;
M is a conjugated moiety;
a1-a11 are the same or different at each occurrence and are an integer of 0-4;
b1 and b2 are the same or different and are an integer of 0-5;
c1 and c2 are the same or different and are an integer of 1-4;
m=2 when E 1 =Si, Ge;
m=1 when E 1 =PO, SiR′, or GeR′;
n1, n2, and n3 are the same or different and are an integer of 0-3;
s and t represent non-zero mole fractions, such that s+t=1;
x is an integer of 1-6;
z is an integer greater than 0; and
Q is a monomeric unit having Formula I-m, Formula IA-m, Formula IIA-m, Formula IIB-m, Formula III-m, or Formula IIIA-m

where * indicates a point of attachment in a copolymer.

2 . The triarylamine of claim 1 , which is at least 10% deuterated.

3 . The triarylamine of claim 1 having Formula I.

4 . The triarylamine of claim 1 having Formula IA.

5 . The triarylamine of claim 1 having Formula III.

6 . The triarylamine of claim 4 having Formula IIIA.

7 . The triarylamine of claim 6 , at least one of R1-R3 is an alkyl or deuterated alkyl.

8 . The triarylamine of claim 6 , at least one of R4-R6 is an alkyl or deuterated alkyl.

9 . The triarylamine of claim 6 , wherein R1, R2, R4 and R5 are an alkyl or deuterated alkyl.

10 . The triarylamine of claim 1 having Formula IV, wherein Q has Formula IA-m.

11 . The triarylamine of claim 1 having Formula IV, wherein Q has Formula IIIA-m.

12 . The triarylamine of claim 11 , wherein at least one of R1-R3 is an alkyl or deuterated alkyl.

13 . The triarylamine of claim 11 , wherein at least one of R4-R6 is an alkyl or deuterated alkyl.

14 . The triarylamine of claim 11 , wherein R1, R2, R4 and R5 are an alkyl or deuterated alkyl.

15 . An electroactive composition comprising
(a) a triarylamine having Formula I, Formula IA, Formula IIA, Formula IIB, Formula III, Formula IIIA, or Formula IV

where:
E is the same or different at each occurrence and is selected from the group consisting of (CR′ 2 ) X , O, (SiR′ 2 ) X , (GeR′ 2 ) X , S, and Se;
E 1 =Si, Ge, PO, SiR′, or GeR′;
R is the same or different at each occurrence and is selected from the group consisting of D, alkyl, silyl, germyl, aryl, deuterated alkyl, deuterated silyl, deuterated germyl, and deuterated aryl, where two adjacent R groups can be joined together to form a cycloaliphatic ring, an aromatic ring, or deuterated analog thereof;
R′ is the same or different at each occurrence and is selected from the group consisting of H, D, alkyl, silyl, germyl, aryl, deuterated alkyl, deuterated silyl, deuterated germyl, and deuterated aryl, where two adjacent R′ groups can be joined together to form a cycloaliphatic ring or deuterated cycloaliphatic ring;
R1-R6 are the same or different and are selected from the group consisting of H, D, C1-8 alkyl, and deuterated C1-8 alkyl;
L is the same or different at each occurrence and is selected from the group consisting of H, D, halogen, alkyl, aryl, crosslinkable groups, deuterated alkyl, deuterated aryl, and deuterated crosslinkable groups;
L 1 is the same or different at each occurrence and is selected from the group consisting of H, D, halogen, aryl, arylamino, crosslinkable groups, deuterated aryl, deuterated arylamino, and deuterated crosslinkable groups;
Ar 1 and Ar 2 are the same or different and are selected from the group consisting of aryl groups and deuterated analogs thereof;
M is a conjugated moiety;
a1-a11 are the same or different at each occurrence and are an integer of 0-4;
b1 and b2 are the same or different and are an integer of 0-5;
c1 and c2 are the same or different and are an integer of 1-4;
m=2 when E 1 =Si, Ge;
m=1 when E 1 =PO, SiR′, or GeR′;
n1, n2, and n3 are the same or different and are an integer of 0-3;
s and t represent non-zero mole fractions, such that s+t=1;
x is an integer of 1-6;
z is an integer greater than 0; and
Q is a monomeric unit having Formula I-m, Formula IA-m, Formula IIA-m, Formula IIB-m, Formula III-m, or Formula IIIA-m

where * indicates a point of attachment in a copolymer; and
(b) an organometallic dopant capable of electroluminescence having an emission maximum between 380 and 750 nm.

16 . The electroactive composition of claim 15 , wherein the triarylamine has Formula IA.

17 . The electroactive composition of claim 15 , wherein the triarylamine has Formula IIIA.

18 . An organic electronic device comprising a first electrical contact layer, a second electrical contact layer, and at least one active layer there between, wherein the active layer comprises a triarylamine having Formula I, Formula IA, Formula IIA, Formula IIB, Formula III, Formula IIIA, or Formula IV

where:
E is the same or different at each occurrence and is selected from the group

Assignees

• Du Pont

Inventors

• Radu Nora Sabina
• Feldman Jerald
• Lecloux Daniel David
• Wang Ying
• Fennimore Adam
• Dobbs Kerwin D
• Rossi Gene M
• Mclaren Charles D
• Gentry Frederick P

Classifications

• C08G2261/95

  Use in organic luminescent diodes · CPC title

• C08G2261/3162

  Arylamines · CPC title

• C08G2261/312

  Non-condensed aromatic systems, e.g. benzene · CPC title

• H01L51/0094

  Electricity · mapped topic

• H01L51/0035 Primary

  Electricity · mapped topic