Electroactive materials
View Patent ↗There is disclosed a compound having Formula I In Formula I: Ar 1 through Ar 4 are the same or different and are aryl groups; L is a spiro group, an adamantyl group, bicyclic cyclohexyl, deuterated analogs thereof, or substituted derivatives thereof; R 1 is the same or different at each occurrence and is D, F, alkyl, aryl, alkoxy, silyl, or a crosslinkable group, where adjacent R 1 groups can be joined together to form an aromatic ring; R 2 is the same or different at each occurrence and is H, D, or halogen; a is the same or different at each occurrence and is an integer from 0-4; and n is an integer greater than 0.
1. A compound having Formula I
wherein:
** indicates a point of attachment or R 2 ;
Ar 1 through Ar 4 are the same or different and are aryl groups;
R 1 is the same or different at each occurrence and is selected from the group consisting of D, F, alkyl, aryl, alkoxy, silyl, and a crosslinkable group, where adjacent R 1 groups can be joined together to form an aromatic ring;
R 2 is the same or different at each occurrence and is selected from the group consisting of H, D, and halogen;
a is the same or different at each occurrence and is an integer from 0-4;
wherein the compound is a small molecule, an oligomer or a polymer, and wherein
is selected from the group consisting of
where:
R is the same or different at each occurrence and is H or R 1 ; and
an asterisk indicates a point of attachment to a nitrogen of an arylamino group.
2. The compound of claim 1 , having Formula II
wherein:
** indicates a point of attachment or R 2 ;
Ar 1 and Ar 2 are the same or different and are aryl groups;
E is the same or different at each occurrence and is selected from the group consisting of a single bond, C(R 3 ) 2 , C(R 4 ) 2 C(R 4 ) 2 , O, Si(R 3 ) 2 , Ge(R 3 ) 2 ;
R 1 is the same or different at each occurrence and is selected from the group consisting of D, F, alkyl, aryl, alkoxy, silyl, and a crosslinkable group, where adjacent R 1 groups can be joined together to form an aromatic ring;
R 2 is the same or different at each occurrence and is selected from the group consisting of H, D, and halogen;
R 3 is the same or different at each occurrence and is selected from the group consisting of H, alkyl and aryl, where adjacent R 3 groups can be joined together to form an aliphatic ring;
R 4 is the same or different at each occurrence and is selected from the group consisting of H, D, and alkyl;
a is the same or different at each occurrence and is an integer from 0-4;
wherein the compound is a small molecule, an oligomer or a polymer, and wherein
is selected from the group consisting of
where:
R is the same or different at each occurrence and is H or R 1 ; and
an asterisk indicates a point of attachment to a nitrogen of an arylamino group.
3. The compound of claim 1 , having Formula III
wherein:
** indicates a point of attachment or R 2 ;
Ar 1 and Ar 2 are the same or different and are aryl groups;
R 1 is the same or different at each occurrence and is selected from the group consisting of D, F, alkyl, aryl, alkoxy, silyl, and a crosslinkable group, where adjacent R 1 groups can be joined together to form an aromatic ring;
R 2 is the same or different at each occurrence and is selected from the group consisting of H, D, and halogen;
R 5 is the same or different at each occurrence and is selected from the group consisting of D, F, alkyl, aryl, alkoxy, silyl, and a crosslinkable group;
R 6 through R 9 are the same or different at each occurrence and are selected from the group consisting of H, D, F, alkyl, aryl, alkoxy, silyl, and a crosslinkable group, with the proviso that at least one of R 6 and R 7 is alkyl or silyl, and at least one of R 8 and R 9 is alkyl or silyl;
a is the same or different at each occurrence and is an integer from 0-4;
b is the same or different at each occurrence and is an integer from 0-2;
wherein the compound is a small molecule, an oligomer or a polymer, and wherein
is selected from the group consisting of
where:
R is the same or different at each occurrence and is H or R 1 ; and
an asterisk indicates a point of attachment to a nitrogen of an arylamino group.
4. The compound of claim 1 , wherein Ar 1 and Ar 2 have Formula a
where:
R 10 is the same or different at each occurrence and is selected from the group consisting of D, alkyl, alkoxy, siloxane and silyl;
c is the same or different at each occurrence and is an integer from 0-4;
d is an integer from 0-5; and
m is an integer from 1 to 5.
5. The compound of claim 1 , wherein Ar 1 and Ar 2 are selected from the group consisting of phenyl, biphenyl, terphenyl, deuterated derivatives thereof, and derivatives thereof having one or more substituents selected from the group consisting of alkyl, alkoxy, silyl, and a substituent with a crosslinking group.
6. The compound of claim 1 , wherein a=0.
7. The compound of claim 2 , wherein R 3 is selected from the group consisting of phenyl, biphenyl, and fluoroalkyl.
8. The compound of claim 3 , wherein R 6 ═R 8 =alkyl.
9. The compound of claim 3 , wherein R 7 ═R 9 =alkyl.
10. An organic electronic device comprising a first electrical contact layer, a second electrical contact layer and an electroactive layer therebetween, wherein the electroactive layer comprises a compound according to claim 1 .
11. The device of claim 10 , wherein the electroactive layer is a hole transport layer.
12. The device of claim 10 , wherein the electroactive layer is an electroactive layer comprising a host compound having Formula I and a dopant.
13. The compound of claim 1 , wherein
14. The compound of claim 1 , wherein
is selected from the group consisting of
15. The compound of claim 1 , wherein
is selected from the group consisting of
16. A compound having Formula I
wherein:
Ar 1 through Ar 4 are the same or different and are aryl groups;
R 1 is the same or different at each occurrence and is selected from the group consisting of D, F, alkyl, aryl, alkoxy, silyl, and a crosslinkable group, where adjacent R 1 groups can be joined together to form an aromatic ring;
R 2 is the same or different at each occurrence and is selected from the group consisting of H, D, and halogen;
a is the same or different at each occurrence and is an integer from 0-4;
n=1; and
wherein
is selected from the group consisting of
where:
R is the same or different at each occurrence and is H or R 1 ; and
an asterisk indicates a point of attachment to a nitrogen of an arylamino group.
17. The compound of claim 16 , wherein Ar 1 and Ar 2 are selected from the group consisting of phenyl, biphenyl, terphenyl, deuterated derivatives thereof, and derivatives thereof having one or more substituents selected from the group consisting of alkyl, alkoxy, silyl, and a substituent with a crosslinking group.
18. The compound of claim 16 , wherein a=0.
19. An organic electronic device comprising a first electrical contact layer, a second electrical contact layer and an electroactive layer therebetween, wherein the electroactive layer comprises a compound according to claim 16 .
20. The compound of claim 1 , wherein the compound is deuterated.