Organic electronic devices using phthalimide compounds
Organic electronic devices comprising a phthalimide compound. The phthalimide compounds disclosed herein are electron transporters with large HOMO-LUMO gaps, high triplet energies, large reduction potentials, and/or thermal and chemical stability. As such, these phthalimide compounds are suitable for use in any of various organic electronic devices, such as OLEDs and solar cells. In an OLED, the phthalimide compounds may serve various functions, such as a host in the emissive layer, as a hole blocking material, or as an electron transport material. In a solar cell, the phthalimide compounds may serve various functions, such as an exciton blocking material. Various examples of phthalimide compounds which may be suitable for use in the present invention are disclosed.
1. An organic electronic device comprising:
an anode;
a cathode; and
an organic layer disposed between the anode and the cathode, wherein the organic layer is capable of transporting electrons and comprises a phthalimide compound having the formula:
wherein R 1 represents one or more independently selected substitutions located on any position of the ring, wherein each substitution is a hydrogen, an alkyl moiety containing up to fifteen carbon atoms, or an aryl moiety, and
wherein R is a phenyl group or a phthalimide-containing group.
2. The device of claim 1 , wherein R is represented by the formula:
wherein R 2 represents one or more independently selected substitutions located on any position of the ring, wherein each substitution is hydrogen, an alkyl moiety containing up to fifteen carbon atoms, or an aryl moiety,
wherein R 8 represents a substitution located on any position of the ring, wherein R 8 is represented by the formula:
wherein R 3 represents one or more independently selected substitutions located on any position of the ring, wherein each substitution is a hydrogen, an alkyl moiety containing up to fifteen carbon atoms, or an aryl moiety.
3. The device of claim 2 , wherein the two phthalimide groups are in para position on the phenyl ring.
4. The device of claim 1 , wherein R is represented by the formula:
wherein R 4 represents one or more independently selected substitutions located on any position of the ring, wherein each substitution is hydrogen, an alkyl moiety containing up to fifteen carbon atoms, or an aryl moiety, and
wherein R 5 represents a substitution located on any position of the ring, wherein R 5 is represented by the formula:
wherein R 6 represents one or more independently selected substitutions located on any position of the ring, wherein each substitution is hydrogen, an alkyl moiety containing up to fifteen carbon atoms, or an aryl moiety.
5. The device of claim 4 , wherein the two phthalimide groups are in ortho position on the cyclohexane ring.
6. The device of claim 1 , wherein R is represented by the formula:
wherein R 7 represents one or more independently selected substitutions located on any position of the ring, wherein each substitution is hydrogen, an alkyl moiety containing up to fifteen carbon atoms, or an aryl moiety.
7. The device of claim 1 , wherein R is represented by the formula:
wherein R 9 represents one or more independently selected substitutions located on any position of the ring, wherein each substitution is hydrogen, an alkyl moiety containing up to fifteen carbon atoms, or an aryl moiety.
8. The device of claim 1 , wherein the phthalimide compound is a bis-phthalimide.
9. The device of claim 1 , wherein the phthalimide compound is selected from the group consisting of:
10. The device of claim 1 , wherein the phthalimide compound is selected from the group consisting of:
11. The device of claim 1 , wherein the device is an organic light-emitting device.
12. The device of claim 11 , wherein the organic layer is an electron transport layer.
13. The device of claim 1 , wherein the device is a solar cell.
14. The device of claim 13 , wherein the organic layer is an exciton blocking layer.
15. The device of claim 1 , wherein the phthalimide compound has the formula:
wherein R A represents one or more independently selected substitutions located on any position of the ring, wherein each substitution is a hydrogen, an alkyl moiety containing up to fifteen carbon atoms, or an aryl moiety,
wherein R B represents one or more independently selected substitutions located on any position of the ring, wherein each substitution is a hydrogen, an alkyl moiety containing up to fifteen carbon atoms, or an aryl moiety, and
wherein L is a 6-membered ring or a direct bond between the two phthalimide groups.
16. The device of claim 15 , wherein L is a cyclohexane ring represented by the formula:
wherein R C represents one or more independently selected substitutions located on any position of the ring, wherein each substitution is a hydrogen, an alkyl moiety containing up to fifteen carbon atoms, or an aryl moiety, and
wherein the two phthalimide groups are in ortho, meta, or para position on the cyclohexane ring.
17. The device of claim 15 , wherein L is an phenyl ring represented by the formula:
wherein R D represents one or more independently selected substitutions located on any position of the ring, wherein each substitution is a hydrogen, an alkyl moiety containing up to fifteen carbon atoms, or an aryl moiety, and
wherein the two phthalimide groups are in ortho, meta, or para position on the phenyl ring.
18. The device of claim 17 , wherein L is represented by the formula:
wherein the two phthalimide groups are in para position.
19. The device of claim 18 , wherein L is represented by the formula:
20. The device of claim 18 , wherein L is represented by the formula:
21. The device of claim 16 , wherein L is represented by the formula:
wherein the two phthalimide groups are in ortho position.
22. The device of claim 21 , wherein L is represented by the formula: