Solvent-resistant hole transport layers

Patent metadata

Field	Value
Publication number	US-2016308141-A1
Application number	US-201415101133-A
Country	US
Kind code	A1
Filing date	Dec 9, 2014
Priority date	Dec 12, 2013
Publication date	Oct 20, 2016
Grant date	—

Abstract

There is provided a hole transport material having Formula I, Formula Ia, or Formula II: In the formulae: A is an aromatic moiety including at least one triarylamino group; B′ is an aromatic moiety; E is an end group which is H, D, alkyl, aryl, halide, deuterated alkyl, or deuterated aryl; G is G1, G2, or a deuterated analog thereof where the asterisk represents the point of attachment; n is an integer greater than 0; and m1 and m2 represent non-zero mole fractions, such that m1+m2=1.

First claim

What is claimed is:

1 . A hole transport material having Formula I, Formula Ia, or Formula II:

wherein:
A is an aromatic moiety comprising at least one triarylamino group;
B′ is an aromatic moiety;
E is the same or different at each occurrence and is an end group selected from the group consisting of H, D, halide, alkyl, aryl, deuterated alkyl, and deuterated aryl;
G is selected from the group consisting of G1, G2, and deuterated analogs thereof

where the asterisk represents the point of attachment;
n is an integer greater than 0;
m1 and m2 represent non-zero mole fractions, such that m1+m2=1.

2 . A hole transport material comprising:
(a) a material having at least one triarylamino group; and (b) a material having Formula III, Formula IIIa, or Formula IV:

wherein:
J is an aromatic moiety;
K is selected from the group consisting of alkyl, aryl, substituted derivatives thereof, and deuterated analogs thereof;
M is selected from he group consisting of alkyl, aryl, substituted derivatives thereof, and deuterated analogs thereof;
E is the same or different at each occurrence and is an end group selected from the group consisting of H, D, halide, alkyl, aryl, deuterated alkyl, and deuterated aryl;
G is selected from the group consisting of G1, G2, and deuterated analogs thereof

where the asterisk represents the point of attachment;
n is an integer greater than 0;
s1 and s2 represent mole fractions, such that s2≠0 and s1+s2=1.

3 . A process for making a hole transport layer comprising the steps:
(1) providing a first liquid composition comprising a first liquid medium having dispersed therein a material having Formula I, Formula Ia, or Formula II:

wherein:
A is an aromatic moiety comprising at least one triarylamino group;
B′ is an aromatic moiety;
E is the same or different at each occurrence and is an end group selected from the group consisting of H, D, halide, alkyl, aryl, deuterated alkyl, and deuterated aryl;
G is selected from the group consisting of G1, G2, and deuterated analogs thereof

where the asterisk represents the point of attachment;
n is an integer greater than 0;
m1 and m2 represent non-zero mole fractions, such that m1+m2=1;
(2) depositing the first liquid composition onto a workpiece to form a deposited layer; and
(3) baking the deposited layer at a predetermined temperature for a predetermined time to form a hole transport layer.

4 . A process for making a hole transport layer, comprising the steps:
(1) providing a first liquid composition comprising a first liquid medium having dispersed therein a hole transport composition comprising: (a) a material having at least one triarylamino group; and (b) a material having Formula III, Formula IIIa, or Formula IV:

wherein:
J is an aromatic moiety;
K is selected from the group consisting of alkyl, aryl, substituted derivatives thereof, and deuterated analogs thereof;
M is selected from the group consisting of alkyl, aryl, substituted derivatives thereof, and deuterated analogs thereof;
E is the same or different at each occurrence and is an end group selected from the group consisting of H, D, halide, alkyl, aryl, deuterated alkyl, and deuterated aryl;
G is selected from the group consisting of G1, G2, and deuterated analogs thereof

where the asterisk represents the point of attachment;
n is an integer greater than 0;
s1 and s2 represent mole fractions, such that s2≠0 and s1+s2=1;
(2) depositing the first liquid composition onto a workpiece to form a deposited layer; and
(3) baking the deposited layer at a predetermined temperature for a predetermined time to form a hole transport layer.

5 . An organic electronic device comprising an anode, a cathode, and a hole transport layer therebetween, wherein the hole transport layer is made from a hole transport material having Formula Formula Ia, or Formula II:

wherein:
A is an aromatic moiety comprising at least one triarylamino group;
B′ is an aromatic moiety;
E is the same or different at each occurrence and is an end group selected from the group consisting of H, D, halide, alkyl, aryl, deuterated alkyl, and deuterated aryl;
G is selected from the group consisting of G1, G2, and deuterated analogs thereof

where the asterisk represents the point of attachment;
n is an integer greater than 0;
m1 and m2 represent non-zero mole fractions, such that m1+m2=1.

6 . An organic electronic device comprising an anode, a cathode, and a hole transport layer therebetween, wherein the hole transport layer is made from a hole transport material comprising:
(a) a material having at least one triarylamino group; and (b) a material having Formula III, Formula IIIa, or Formula IV:

wherein:
J is an aromatic moiety;
K is selected from the group consisting of alkyl, aryl, substituted derivatives thereof, and deuterated analogs thereof;
M is selected from the group consisting of alkyl, aryl, substituted derivatives thereof, and deuterated analogs thereof;
E is the same or different at each occurrence and is an end group selected from the group consisting of H, D, halide, alkyl, aryl, deuterated alkyl, and deuterated aryl;
G is selected from the group consisting of G1, G2, and deuterated analogs thereof

where the asterisk represents the point of attachment;
n is an integer greater than 0;
s1 and s2 represent mole fractions, such that s2≠0 and s1+s2=1.

Assignees

• Du Pont

Inventors

• Radu Nora Sabina
• Fennimore Adam

Classifications

• C08G2261/3162

  Arylamines · CPC title

• C08G61/10

  only aromatic carbon atoms, e.g. polyphenylenes · CPC title

• C08G2261/312

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

• C08G2261/148

  Side-chains having aromatic units · CPC title

• C08G2261/412

  Yamamoto reactions · CPC title