Electroactive materials
There is provided a compound having Formula I In Formula I: BCz is a substituted or unsubstituted benzocarbazole unit; L 1 and L 2 are the same or different and are H, D, halogen, aryl, arylamino, crosslinkable groups, deuterated aryl, deuterated arylamino, or deuterated crosslinkable groups; Q 1 and Q 2 are the same or different and are a single bond, alkyl, aryl, heteroaryl, diarylamino, triarylamino, deuterated alkyl, deuterated aryl, deuterated heteroaryl, deuterated diarylamino, or deuterated triarylamino; and n is an integer greater than 0, with the proviso that when n=1, L 1 and L 2 are Cl, Br, crosslinkable groups or deuterated crosslinkable groups.
1. A compound having Formula I
wherein:
BCz is a substituted or unsubstituted benzocarbazole unit;
L 1 and L 2 are the same or different and are selected from the group consisting of H, D, halogen, aryl, arylamino, crosslinkable groups, deuterated aryl, deuterated arylamino, and deuterated crosslinkable groups;
Q 1 and Q 2 are the same or different and are selected from the group consisting of a single bond, alkyl, aryl, diarylamino, triarylamino, deuterated alkyl, deuterated aryl, deuterated diarylamino, and deuterated triarylamino, wherein at least one of Q 1 or Q 2 is not a single bond; and
n is an integer of 10 to 100,000.
2. The compound of claim 1 , wherein BCz is selected from the group consisting of BCz-A, BCz-B, and BCz-C
wherein:
R′ is selected from the group consisting of alkyl, cycloalkyl, fluoroalkyl, silyl, germyl, aryl, heteroaryl, triarylamino, and deuterated analogs thereof;
R 1 and R 2 are the same or different at each occurrence and are selected from the group consisting of D, F, CN, aryl, heteroaryl, aryloxy, fluoroaryl, alkyl, fluoroalkyl, alkoxy, fluoroalkoxy, amino, silyl, siloxane, siloxy, germyl, deuterated aryl, deuterated heteroaryl, deuterated aryloxy, deuterated fluoroaryl, deuterated alkyl, deuterated fluoroalkyl, deuterated alkoxy, deuterated fluoroalkoxy, deuterated amino, deuterated silyl, deuterated siloxane, deuterated siloxy, and deuterated germyl, wherein adjacent R′ and/or R 2 groups can be joined together to form a fused ring;
a is an integer from 0-3;
b is an integer from 0-5; and
* indicates a point of attachment to Q 1 or Q 2 .
3. The compound of claim 1 , wherein BCz is selected from the group consisting of BCz-A1, BG-B1 and BCz-C1
where
R″ is selected from the group consisting of alkyl, cycloalkyl, fluoroalkyl, silyl, germyl, aryl, heteroaryl, triarylamino, and deuterated analogs thereof;
R 1 and R 2 are the same or different at each occurrence and are selected from the group consisting of D, F, CN, aryl, heteroaryl, aryloxy, fluoroaryl, alkyl, fluoroalkyl, alkoxy, fluoroalkoxy, amino, silyl, siloxane, siloxy, germyl, deuterated aryl, deuterated heteroaryl, deuterated aryloxy, deuterated fluoroaryl, deuterated alkyl, deuterated fluoroalkyl, deuterated alkoxy, deuterated fluoroalkoxy, deuterated amino, deuterated silyl, deuterated siloxane, deuterated siloxy, and deuterated germyl, wherein adjacent R 1 and/or R 2 groups can be joined together to form a fused ring;
a is an integer from 0-3;
c is an integer from 0-6; and
* indicates a point of attachment to Q 1 or Q 2 .
4. The compound of claim 1 , wherein BCz is selected from the group consisting of BCz-A2, BCz-B2, and BCz-C2
where
R″ is selected from the group consisting of alkyl, cycloalkyl, fluoroalkyl, silyl, germyl, aryl, heteroaryl, triarylamino, and deuterated analogs thereof;
R 1 and R 2 are the same or different at each occurrence and are selected from the group consisting of D, F, CN, aryl, heteroaryl, aryloxy, fluoroaryl, alkyl, fluoroalkyl, alkoxy, fluoroalkoxy, amino, silyl, siloxane, siloxy, germyl, deuterated aryl, deuterated heteroaryl, deuterated aryloxy, deuterated fluoroaryl, deuterated alkyl, deuterated fluoroalkyl, deuterated alkoxy, deuterated fluoroalkoxy, deuterated amino, deuterated silyl, deuterated siloxane, deuterated siloxy, and deuterated germyl, wherein adjacent R′ and/or R 2 groups can be joined together to form a fused ring;
b is an integer from 0-5;
d is an integer from 0-4; and
* indicates a point of attachment to Q 1 or Q 2 .
5. The compound of claim 1 , wherein Q 1 is a hydrocarbon aryl group having 6-36 ring carbons or deuterated analog.
6. The compound of claim 1 , wherein Q 1 is a diarylamino group having Formula e
where:
R′ is selected from the group consisting of alkyl, cycloalkyl, fluoroalkyl, silyl, germyl, aryl, heteroaryl, triarylamino, and deuterated analogs thereof;
Ar 4 is selected from the group consisting of aryl, heteroaryl, and deuterated analogs thereof;
# indicates a point of attachment; and
## indicates a point of attachment to BCz.
7. The compound of claim 6 , wherein R′ is a hydrocarbon aryl group and has at least one substituent selected from the group consisting of D, F, CN, alkyl, alkoxy, silyl, siloxy, siloxane, aryl, heteroaryl, diarylamino, carbazolyl, deuterated alkyl, deuterated alkoxy, deuterated silyl, deuterated siloxy, deuterated siloxane, deuterated aryl, deuterated heteroaryl, deuterated diarylamino, and deuterated carbazolyl.
8. The compound of claim 1 , wherein Q1 is a triarylamino group having Formula f
where:
R″ is selected from the group consisting of alkyl, cycloalkyl, fluoroalkyl, silyl, germyl, aryl, heteroaryl, triarylamino, and deuterated analogs thereof;
Ar 4 , and Ar 5 are the same or different and are selected from the group consisting of aryl, heteroaryl, and deuterated analogs thereof;
# indicates a point of attachment; and
## indicates a point of attachment to BCz.
9. The compound of claim 1 , wherein the compound has Formula I-a
wherein:
R′ is selected from the group consisting of alkyl, cycloalkyl, fluoroalkyl, silyl, germyl, aryl, heteroaryl, triarylamino, and deuterated analogs thereof;
R 1 and R 2 are the same or different at each occurrence and are selected from the group consisting of D, F, CN, aryl, heteroaryl, aryloxy, fluoroaryl, alkyl, fluoroalkyl, alkoxy, fluoroalkoxy, amino, silyl, siloxane, siloxy, germyl, deuterated aryl, deuterated heteroaryl, deuterated aryloxy, deuterated fluoroaryl, deuterated alkyl, deuterated fluoroalkyl, deuterated alkoxy, deuterated fluoroalkoxy, deuterated amino, deuterated silyl, deuterated siloxane, deuterated siloxy, and deuterated germyl, wherein adjacent R 1 and/or R 2 groups can be joined together to form a fused ring;
L 1 and L 2 are the same or different and are selected from the group consisting of H, D, halogen, aryl, arylamino, crosslinkable groups, deuterated aryl, deuterated arylamino, and deuterated crosslinkable groups;
Q1 and Q2 are the same or different and are selected from the group consisting of a single bond, alkyl, aryl, diarylamino, triarylamino, deuterated alkyl, deuterated aryl, deuterated diarylamino, and deuterated triarylamino, wherein at least one of Q 1 or Q 2 is not a single bond;
a is an integer from 0-3;
b is an integer from 0-5; and
n is an integer of 10 to 100,000.
10. An electronic device comprising an anode, a cathode, and an organic active layer therebetween, where the organic active layer comprises the compound of claim 1 .
11. The compound of claim 1 , wherein the compound is a homopolymer.
12. The compound of claim 2 , wherein a=b=0.
13. The compound of claim 2 , wherein R 1 and R 2 are the same or different at each occurrence and are selected from the group consisting of D, F, CN, alkyl, fluoroalkyl, alkoxy, fluoroalkoxy, amino, silyl, siloxane, siloxy, germyl, deuterated alkyl, deuterated fluoroalkyl, deuterated alkoxy, deuterated fluoroalkoxy, deuterated amino, deuterated silyl, deuterated siloxane, deuterated siloxy, and deuterated germyl, wherein adjacent R 1 and/or R 2 groups can be joined together to form a fused ring.