Organic conductive materials and devices
Embodiments described herein relate to compositions including iptycene-based structures and extended iptycene structures. In some embodiments, the compositions may be useful in organic light-emitting diodes (OLEDs), organic photovoltaics, and other devices.
1. A composition, comprising:
an iptycene-based compound comprising an iptycene core including one or more phenyl rings and at least one optionally substituted heterocyclyl or optionally substituted heteroaryl moiety bonded to the iptycene core, wherein the optionally substituted heterocyclyl or optionally substituted heteroaryl moiety defines at least a portion of the iptycene core,
wherein the iptycene-based compound comprises one or more carbazole moieties, and
wherein at least one of the carbazole moieties includes at least one of the phenyl rings of the iptycene core.
2. A composition as in claim 1 , comprising:
a compound having one of the following structures,
wherein:
R 1 -R 20 can be the same or different and are hydrogen, halo, hydroxyl, amino, alkyl, heteroalkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocyclyl, or a carbonyl group, any of which is optionally substituted, or, any two adjacent groups of R 1 -R 20 can be joined together to form an optionally substituted ring,
provided that two adjacent groups of R 1 -R 20 are joined together to form a ring, such that a carbazole moiety is formed including the phenyl ring of the core iptycene structure.
3. A composition as in claim 1 , wherein the compound has the following formula,
wherein:
X 1 -X 5 can be the same or different and are heteroatoms or metal atoms, any of which is optionally substituted or optionally bonded to a polymer;
R 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 , R 16 , R 17 , and R 20 can be the same or different and are hydrogen, halo, hydroxyl, amino, alkyl, heteroalkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocyclyl, or a carbonyl group, any of which is optionally substituted or optionally bonded to a polymer;
each R can be the same or different and is a substituent, optionally substituted or optionally bonded to a polymer; and
n is an integer from 0-4.
4. A composition as in claim 3 , wherein R 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 , R 16 , R 17 , and R 20 are hydrogen and each X 1 -X 5 is NH or N(R′), wherein R′ is an optionally substituted aryl or an optionally substituted heteroaryl.
5. A composition as in claim 4 , wherein R′ is phenyl substituted with one or more electron-withdrawing groups.
6. A composition as in claim 5 , wherein R′ is a group having the following formula,
wherein Y 1 and Y 2 can be the same or different and are hydrogen, halo, cyano, fluoroalkyl, fluoroalkoxy, or a carbonyl group.
7. A composition as in claim 6 , wherein R′ is a group having the following formula,
wherein R″ is alkyl, fluoroalkyl, alkoxy, fluoroalkoxy, and n is 0-5.
8. A composition as in claim 6 , wherein R′ is a group having the following formula,
9. A composition as in claim 4 , wherein R′ is phenyl substituted with one or more electron-donating groups.
10. A composition as in claim 9 , wherein the electron-donating group is alkyl, alkoxy, aryl, heteroaryl, P(aryl) 3 , or Si(aryl) 3 .
11. A composition as in claim 10 , wherein R′ is phenyl substituted with methyl, Phenyl,
12. A composition as in claim 1 , wherein the compound has the following structure,
wherein:
R is hydrogen, alkyl, alkoxy, fluoroalkyl, or fluoroalkoxy; and
R′ is a group having the following formula,
wherein n is 1 or greater.
13. A composition as in claim 12 , wherein R is hydrogen, O-butyl, or CF 3 .
14. A composition as in claim 13 , wherein n is 1-10.
15. A composition as in claim 1 , wherein the compound is bonded to a polymer or is dispersed within a polymer.
16. A device, comprising:
an iptycene-based compound comprising an iptycene core including one or more phenyl rings and at least one heterocyclyl or heteroaryl moiety bonded to the iptycene core, wherein the heterocyclyl or heteroaryl moiety is substituted with at least one electron-withdrawing group and the iptycene-based compound exhibits a solid state singlet-triplet energy gap of about 1 kcal/mol or less; and
two electrodes constructed and arranged to be in electrochemical communication with the iptycene-based compound,
wherein the iptycene-based compound comprises one or more carbazole moieties, and
wherein at least one of the carbazole moieties includes at least one of the phenyl rings of the iptycene core.
17. A device as in claim 16 , wherein the iptycene-based compound exhibits a solid state singlet-triplet energy gap of about 0.5 kcal/mol or less.
18. A device as in claim 16 , wherein the device is an organic light-emitting diode or an organic photovoltaic device.
19. A device as in claim 16 , wherein the iptcyene-based compound has the following structure,
wherein:
X 1 -X 5 can be the same or different and are heteroatoms or metal atoms, any of which is optionally substituted or optionally bonded to a polymer;
R 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 , R 16 , R 17 , and R 20 can be the same or different and are hydrogen, halo, hydroxyl, amino, alkyl, heteroalkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocyclyl, or a carbonyl group, any of which is optionally substituted or optionally bonded to a polymer;
each R can be the same or different and is a substituent, optionally substituted or optionally bonded to a polymer; and
n is an integer from 0-4.
20. A device as in claim 16 , wherein the iptcyene-based compound has the following formula,
wherein:
R is hydrogen, alkyl, alkoxy, fluoroalkyl, or fluoroalkoxy; and
R′ is a group having the following formula,
wherein n is 1 or greater.