Blue luminescent compounds
There is provided a compound having Formula I, Formula II, Formula III, Formula IV, Formula V, or Formula VI:
1. A compound having Formula I, Formula II, Formula III, Formula IV, Formula V, or Formula VI:
wherein:
Ar 1 and Ar 4 are the same or different and are heteroaryl or deuterated heteroaryl, Ar 2 and Ar 3 are the same or different and are hydrocarbon aryl, and where Ar 1 -Ar 4 can be substituted with a group selected from the group consisting of D, F, CN, alkyl, fluoroalkyl, aryl, N-heteroaryl, silyl, germyl, deuterated alkyl, deuterated partially-fluorinated alkyl, deuterated aryl, deuterated heteroaryl, deuterated silyl, and deuterated germyl;
Q 1 and Q 2 are the same or different and are selected from the group consisting of nil, a single bond connecting the two aryl groups on the nitrogen, (CR 5 2 ) w , NR 6 , O, S, and Se, with the proviso that at least one of Q 1 and Q 2 is not nil;
R 1 , R 2 and R 4 are the same or different at each occurrence and are selected from the group consisting of D, F, CN, alkyl, alkoxy, fluoroalkyl, aryl, aryloxy, heteroaryl, silyl, siloxane, siloxy, germyl, deuterated alkyl, deuterated partially-fluorinated alkyl, deuterated alkoxy, deuterated aryl, deuterated heteroaryl, deuterated heteroaryl deuterated silyl, deuterated siloxane, deuterated siloxy, and deuterated germyl;
R 3 is the same or different at each occurrence and is selected from the group consisting of alkyl, silyl, germyl, aryl, and deuterated analogs thereof, where two alkyl R 3 groups can be joined together to make a cycloalkyl spiro ring, and where two R 3 phenyl groups can be joined to form a spiro fluorene group;
R 5 is the same or different at each occurrence and is selected from the group consisting of H, D, F, alkyl, fluoroalkyl, deuterated alkyl, or deuterated partially-fluorinated alkyl;
R 6 is selected from the group consisting of aryl and deuterated aryl;
a and b are the same or different and are 0 or 1, with the proviso that a+b≥1, and with the proviso that when a=1 and b=0, Q1 is not a single bond, and, in Formula V, with the proviso that when a=1 and b=0, Q1 is not NR 6 ;
w is an integer of 1-6;
x is an integer of 0-4, with the proviso that when a=1, x=0-3;
y is an integer of 0-6, with the proviso that when b=1, y=0-5;
z is an integer of 0-5, with the proviso that when Q 1 is not nil, z is 0-4; and
z1 is an integer of 0-5, with the proviso that when Q 2 is not nil, z1 is 0-4.
2. The compound of claim 1 having Formula I-a
3. The compound of claim 1 having Formula II-a
4. The compound of claim 1 , wherein at least one of Q 1 and Q 2 is a single bond.
5. The compound of claim 1 , wherein at least one of Q 1 and Q 2 is (CR 5 2 ).
6. The compound of claim 1 , wherein x=y=0.
7. The compound of claim 1 , wherein x>0 and at least one R 1 is D.
8. The compound of claim 1 , wherein y>0 and at least one R 2 is D.
9. The compound of claim 1 , wherein R 3 is selected from the group consisting of alkyl and deuterated alkyl having 1-12 carbons.
10. The compound of claim 1 , wherein at least one of Ar 1 -Ar 4 is an N-heteroaryl selected from the group consisting of pyrrole, pyridine, pyrimidine, carbazole, imidazole, benzimidazole, imidazolobenzimidazole, triazole, benzotriazole, triazolopyridine, indolocarbazole, phenanthroline, quinoline, isoquinoline, quinoxaline, indole, indoloindole, substituted derivatives thereof, and deuterated analogs thereof.
11. The compound of claim 10 , wherein the N-heteroaryl is a carbazole or deuterated carbazole.
12. The compound of claim 1 , wherein a=b=1.
13. The compound of claim 1 , wherein the N-heteroaryl is selected from the group consisting of pyrrole, pyridine, pyrimidine, carbazole, imidazole, benzimidazole, imidazolobenzimidazole, triazole, benzotriazole, triazolopyridine, indolocarbazole, phenanthroline, quinoline, isoquinoline, quinoxaline, indole, indoloindole, substituted derivatives thereof, and deuterated analogs thereof.
14. The compound of claim 1 , wherein the compound is selected from the group consisting of following compounds:
15. An electronic device comprising an anode and a cathode with a photoactive layer therebetween, wherein the photoactive layer comprises a compound having Formula I, Formula II, Formula III, Formula IV, Formula V, or Formula VI:
wherein:
Ar 1 and Ar 4 are the same or different and are heteroaryl or deuterated heteroaryl, Ar 2 and Ar 3 are the same or different and are hydrocarbon aryl, and where Ar 1 -Ar 4 can be substituted with a group selected from the group consisting of D, F, CN, alkyl, fluoroalkyl, aryl, N-heteroaryl, silyl, germyl, deuterated alkyl, deuterated partially-fluorinated alkyl, deuterated aryl, deuterated heteroaryl, deuterated silyl, and deuterated germyl;
Q 1 and Q 2 are the same or different and are selected from the group consisting of nil, a single bond connecting the two aryl groups on the nitrogen, (CR 5 2 ) w , NR 6 , O, S, and Se, with the proviso that at least one of Q 1 and Q 2 is not nil;
R 1 , R 2 and R 4 are the same or different at each occurrence and are selected from the group consisting of D, F, CN, alkyl, alkoxy, fluoroalkyl, aryl, aryloxy, heteroaryl, silyl, siloxane, siloxy, germyl, deuterated alkyl, deuterated partially-fluorinated alkyl, deuterated alkoxy, deuterated aryl, deuterated heteroaryl, deuterated heteroaryl deuterated silyl, deuterated siloxane, deuterated siloxy, and deuterated germyl;
R 3 is the same or different at each occurrence and is selected from the group consisting of alkyl, silyl, germyl, aryl, and deuterated analogs thereof, where two alkyl R 3 groups can be joined together to make a cycloalkyl spiro ring, and where two R 3 phenyl groups can be joined to form a spiro fluorene group;
R 5 is the same or different at each occurrence and is selected from the group consisting of H, D, F, alkyl, fluoroalkyl, deuterated alkyl, or deuterated partially-fluorinated alkyl;
R6 is selected from the group consisting of aryl and deuterated aryl;
a and b are the same or different and are 0 or 1, with the proviso that a+b≥1, and with the proviso that when a=1 and b=0, Q1 is not a single bond, and, in Formula V, with the proviso that when a=1 and b=0, Q1 is not NR 6 ;
w is an integer of 1-6;
x is an integer of 0-4, with the proviso that when a=1, x=0-3;
y is an integer of 0-6, with the proviso that when b=1, y=0-5;
z is an integer of 0-5, with the proviso that when 01 is not nil, z is 0-4; and
z1 is an integer of 0-5, with the proviso that when 02 is not nil, z1 is 0-4.
16. The device of claim 15 , wherein the photoactive layer further comprises a host material selected from the group consisting of anthracenes, chrysenes, pyrenes, phenanthrenes, triphenylenes, phenanthrolines, naphthalenes, triazines, quinolines, isoquinolines, quinoxalines, phenylpyridines, benzodifurans, metal quinolinate complexes, indolofluorenes, indolocarbazoles, indoloindoles, deuterated analogs thereof, and combinations thereof.
17. The device of claim 15 , wherein a=b=1.
18. The device of claim 15 , wherein the N-heteroaryl is selected from the group consisting of pyrrole, pyridine, pyrimidine, carbazole, imidazole, benzimidazole, imidazolobenzimidazole, triazole, benzotriazole, triazolopyridine, indolocarbazole, phenanthroline, quinoline, isoquinoline, quinoxaline, indole, indoloindole, substituted derivatives thereof, and deuterated analogs thereof.