Semiconducting compounds and optoelectronic devices incorporating same
Disclosed are new compounds having semiconducting properties. Such compounds can be processed in solution-phase into thin film semiconductors that exhibit high carrier mobility and/or good current modulation characteristics.
1. A compound represented by formula I:
wherein:
Ar is an optionally substituted C 6-20 aryl group or an optionally substituted 5-20 membered heteroaryl group;
Ar′ is an optionally substituted C 6-20 aryl group or an optionally substituted 5-20 membered heteroaryl group;
R 1 and R 2 , at each occurrence, independently are selected from the group consisting of a halogen, —CN, and -L-R, wherein L, at each occurrence, is selected from —O—, —S—, —Se—, —C(O)—, —OC(O)—, —C(O)O—, and a covalent bond; and R, at each occurrence, independently is selected from the group consisting of a C 1-40 alkyl group, a C 2-40 alkenyl group, a C 2-40 alkynyl group, and a C 1-40 haloalkyl group;
X is selected from the group consisting of —O—, —S—, and —Se—;
X′ is —CR 3 , wherein R 3 is selected from the group consisting of H, a halogen, —CN, and -L′-R′, wherein L′ is selected from the group consisting of —O—, —S—, —Se—, —C(O)—, —OC(O)—, —C(O)O—, and a covalent bond; and R′ is selected from the group consisting of a C 1-40 alkyl group, a C 2-40 alkenyl group, a C 2-40 alkynyl group, and a C 1-40 haloalkyl group;
Y and Y′, independently, are CH or N;
m is 0, 1, 2, 3, 4 or 5;
n is 0, 1, 2, 3 or 4; and
p is 0 or 1.
2. The compound of claim 1 , wherein X is S or Se.
3. The compound of claim 1 , wherein the compound is represented by formula II:
wherein Ar, Ar′, R 1 , R 2 , Y, Y′, m, n and p are as defined in claim 1 .
4. The compound of claim 1 , wherein the compound is represented by formula III:
wherein Ar, Ar′, R 2 , m and p are as defined in claim 1 .
5. The compound of claim 1 , wherein the compound is represented by formula IV:
wherein:
Ar 1 is an optionally substituted C 6-14 aryl group or an optionally substituted 5-14 membered heteroaryl group;
W is selected from the group consisting of —CR 3 ═CR 3 —, —O—, —S—, and —Se—;
W′ is —CR 3 ═ or —N═; and
R 2 , R 3 , and m are as defined in claim 1 .
6. The compound of claim 5 , wherein the compound is represented by formula V:
wherein Ar 1 , R 2 , and m are as defined in claim 5 .
7. The compound of claim 6 , wherein the moiety
is selected from the group consisting of:
wherein:
V″, at each occurrence, independently is —CR 4 ═ or —N═;
Z, at each occurrence, independently is selected from the group consisting of —O—, —S—, and —Se—;
Z′, at each occurrence, independently is —CR 4 ═ or —N═; and
R 4 , at each occurrence, independently is selected from the group consisting of H, a halogen, —CN, and L′R′, wherein L′, at each occurrence, is selected from the group consisting of —O—, —S—, —Se—, —C(O)—, —OC(O)—, —C(O)O—, and a covalent bond; and R′, at each occurrence, independently is selected from the group consisting of a C 1-40 alkyl group, a C 2-40 alkenyl group, a C 2-40 alkynyl group, and a C 1-40 haloalkyl group.
8. The compound of claim 7 , wherein the moiety
is selected from the group consisting of:
wherein any of the carbon atoms optionally is substituted with a halogen, —CN, or -L′-R′, wherein L′, at each occurrence, is selected from the group consisting of —O—, —S—, —Se—, —C(O)—, —OC(O)—, —C(O)O—, and a covalent bond; and R′, at each occurrence, independently is selected from the group consisting of a C 1-40 alkyl group, a C 2-40 alkenyl group, a C 2-40 alkynyl group, and a C 1-40 haloalkyl group.
9. The compound of claim 1 , wherein the compound has a formula selected from the group consisting of:
wherein R 2 and m are as defined in claim 1 .
10. The compound of claim 9 , wherein R 2 is a C 1-40 alkyl group or a C 1-40 haloalkyl group; and m is 0, 1 or 2.
11. An electronic, optical or optoelectronic device comprising a semiconductor component, the semiconductor component comprising a compound according to claim 1 .
12. The device of claim 11 , wherein the semiconductor component is photoactive, and wherein the compound of claim 1 functions as an electron-conducting compound and is present in a blend material.
13. The device of claim 11 , wherein the semiconductor component is photoactive, and wherein the compound of claim 1 functions as a hole-conducting compound and is present in a blend material.
14. The device of claim 11 , wherein the semiconductor component is photoactive, and wherein the compound of claim 1 functions as an light-emitting compound and is present in a blend material.
15. The device of claim 11 configured as an organic light emitting diode comprising a substrate, an anode, a cathode, and in between the anode and the cathode the semiconductor component.
16. The device of claim 11 configured as an organic transistor, further comprising a source electrode, a drain electrode, a gate electrode, and a dielectric layer, wherein the dielectric layer is in contact with the semiconductor component on one surface, and the gate electrode on an opposite surface.
17. The device of claim 16 , wherein the organic transistor is an organic field-effect transistor.
18. The device of claim 16 , wherein the organic transistor is an organic light-emitting transistor.
19. The device of claim 18 , wherein the semiconductor component is photoactive, and wherein the compound of claim 1 functions as an electron-conducting compound or a hole-conducting compound and is present in a blend material.
20. The device of claim 18 , wherein the semiconductor component is photoactive, and wherein the compound of claim 1 functions as an light-emitting compound and is present in a blend material.