Solvent-resistant hole transport layers

Patent metadata

Field	Value
Publication number	US-10586929-B2
Application number	US-201415101133-A
Country	US
Kind code	B2
Filing date	Dec 9, 2014
Priority date	Dec 12, 2013
Publication date	Mar 10, 2020
Grant date	Mar 10, 2020

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 selected from the group consisting of formula A-2, formula A-3, and formula A-4

wherein:
Ar 3 , Ar 4 , Ar 4a , Ar 5 and Ar 5a are the same or different and are aryl groups;
L is the same or different at each occurrence and is aryl, (CR′2)q, adamantyl, bicyclic cyclohexyl, or a bicyclic group having aliphatic rings connected through a single atom;
R′ is the same or different at each occurrence and is H, D, alkyl, fluoroalkyl, aryl, deuterated alkyl, deuterated fluoroalkyl, and deuterated aryl;
X is the same or different at each occurrence and is selected from an aryl group, and a deuterated aryl group, with the proviso that N is not bonded directly to G;
n is an integer greater than 0;
n1 is 0 or 1;
q is an integer from 1-5; and
In Formula Ia, G is bonded directly or through a substituent group to one or more of Ar 4 , Ar 4a , Ar 5 , or Ar 5a

wherein:
Ar 6 and Ar 7 are the same or different and are aryl groups;
R 1 through R 5 are independently the same or different at each occurrence and are selected from the group consisting of D, F, alkyl, aryl, alkoxy, silyl, deuterated alkyl, deuterated aryl, deuterated alkoxy, and deuterated silyl;
a through e are independently an integer from 0 to 4;
f is 1 or 2;
g is 0, 1 or 2;
h is 1 or 2; and
In Formula Ia, G is bonded directly or through a substituent group to one or more of Ar 6 , Ar 7 , R 2 , R 3 , R 4 or R 5

wherein:
Ar 8 is the same or different at each occurrence and is selected from the group consisting of phenylene, substituted phenylene, naphthylene, substituted naphthylene, and deuterated analogs thereof;
Ar 9 is the same or different at each occurrence and is an aryl group;
T 1 and T 2 are independently the same or different at each occurrence and are conjugated moieties which are connected in a non-planar configuration;
k is the same or different at each occurrence and is an integer from 1 to 6;
1 is the same or different at each occurrence and is an integer from 1 to 6; and
In Formula Ia, G is bonded directly or through a substituent group to one or more of Ar 8 or Ar 9 ;
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; and
m1 and m2 represent non-zero mole fractions, such that m1+m2=1.

2. The hole transport material of claim 1 having Formula I.

3. The hole transport material of claim 1 having Formula Ia.

4. The hole transport material of claim 1 having Formula II.

5. The hole transport material of claim 1 , wherein G is selected from the group consisting of G1-a, G1-b, G1-c, G1-d, and mixtures thereof

6. The hole transport material of claim 5 , wherein G is selected from the group consisting of G1-b, G1-c, and mixtures thereof.

7. The hole transport material of claim 1 , wherein G is selected from the group consisting of G2-a, G2-b, and mixtures thereof

8. The hole transport material of claim 7 , wherein G is G2-b.

9. A hole transport material having Formula Ia or Formula II:

wherein:
A has formula A-1

wherein:
Ar 1 -Ar 2 are the same or different and are aryl groups; and
X is the same or different at each occurrence and is selected from an aryl group, and a deuterated aryl group, with the proviso that N is not bonded directly to G; and
in Formula Ia, G is bonded directly or through a substituent group to Ar 2 ;
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, 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; and
m1 and m2 represent non-zero mole fractions, such that m1+m2=1.

10. The hole transport material of claim 1 , wherein B′ has formula B-1

wherein:
Ar 1 -Ar 2 are the same or different and are aryl groups; and
X is the same or different at each occurrence and is selected from a single bond, an aryl group, and a deuterated aryl group.

11. The hole transport material of claim 1 , wherein B′ has formula B-2

wherein:
Ar 3 -Ar 5 are the same or different and are aryl groups;
L is the same or different at each occurrence and is aryl, (CR′2)q, adamantyl, bicyclic cyclohexyl, or a bicyclic group having aliphatic rings connected through a single atom;
R′ is the same or different at each occurrence and is H, D, alkyl, fluoroalkyl, aryl, deuterated alkyl, deuterated fluoroalkyl, and deuterated aryl;
X is the same or different at each occurrence and is selected from a single bond, an aryl group, and a deuterated aryl group;
p is the same or different at each occurrence and is 0 or 1, with the proviso that at least one p=1; and
q is an integer from 1-5.

12. The hole transport material of claim 1 , wherein B′ has formula B-3

wherein:
Ar 6 and Ar 7 are the same or different and are aryl groups;
R 1 through R 5 are independently the same or different at each occurrence and are selected from the group consisting of D, F, alkyl, aryl, alkoxy, silyl, deuterated alkyl, deuterated aryl, deuterated alkoxy, and deuterated silyl;
a through e are independently an integer from 0 to 4;
f is 1 or 2;
g is 0, 1 or 2; h is 1 or 2; and
p is the same or different at each occurrence and is 0 or 1, with the proviso that at least one p=1.

13. The hole transport material of claim 1 , wherein B′ has formula B-4

wherein:
Ar 8 is the same or different at each occurrence and is selected from the group consisting of phenylene, substituted phenylene, naphthylene, substituted naphthylene, and

Assignees

• Lg Chemical Ltd

Inventors

• Radu Nora Sabina
• Fennimore Adam

Classifications

• C08G2261/95

  Use in organic luminescent diodes · CPC title

• C08G2261/312

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

• C08G2261/3162

  Arylamines · CPC title

• C08G2261/148

  Side-chains having aromatic units · CPC title

• C08G2261/1412

  Saturated aliphatic units · CPC title