Hole transport materials having a sulfur-containing group
Novel materials are provided, having a single phenyl or a chain of phenyls where there is a nitrogen atom on each end of the single phenyl or chain of phenyls. The nitrogen atom may be further substituted with particular thiophene, benzothiophene, and triphenylene groups. Organic light-emitting devices are also provided, where the novel materials are used as a hole transport material in the device. Combinations of the hole transport material with specific host materials are also provided.
1. A composition of matter having the chemical structure:
wherein n is 1, 2 or 3, and the phenyl rings between the nitrogen atoms may be attached to each other and to the nitrogen atoms in a para or meta configuration independently selected for each attachment;
wherein each of R 2 , R 3 and R 4 are independently selected from the group consisting of:
wherein R 1 is selected from the group consisting of:
wherein the dotted line shows the point of attachment to an N atom of Formula I;
wherein at least one of R 2 , R 3 , and R 4 is selected from the group consisting of:
wherein each of R 1 , R 2 , R 3 and R 4 may be further substituted with substituents that are not fused to R 1 , R 2 , R 3 and R 4 .
2. The composition of matter of claim 1 , wherein the part of the composition represented by Formula I is more specifically:
3. The composition of matter of claim 1 , wherein at least one of R 2 , R 3 , and R 4 is
4. The composition of matter of claim 1 , wherein at least one of R 2 , R 3 and R 4 is
5. The composition of matter of claim 1 , wherein both R 1 and R 2 are
6. A composition of matter having the chemical structure:
wherein n is 1, 2, or 3, and the phenyl rings between the nitrogen atoms may be attached to each other and to the nitrogen atoms in a para or meta configuration independently selected for each attachment;
wherein each of R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of:
wherein the dotted line shows the point of attachment to an N atom of Formula I;
wherein at least one of R 1 , R 2 , R 3 , and R 4 is
wherein each of R 1 , R 2 , R 3 , and R 4 may be further substituted with substituents that are not fused to R 1 , R 2 , R 3 , and R 4 .
7. The composition of matter of claim 1 , wherein
at least one of R 2 , R 3 , and R 4 is selected from the group consisting of:
8. The composition of matter of claim 1 , wherein
R 1 is selected from the group consisting of:
each of R 1 , R 2 , R 3 , and R 4 is independently selected from the group consisting of:
and there are no further substitutions to R 1 , R 2 , R 3 , and R 4 .
9. The composition of matter of claim 3 , wherein the composition of matter has a structure selected from the group consisting of:
10. The composition of matter of claim 9 , wherein the composition of matter has the structure:
11. The composition of matter of claim 4 , wherein the composition of matter has a structure selected from the group consisting of:
12. The composition of matter of claim 11 , wherein the composition of matter has the structure:
13. The composition of matter of claim 5 , wherein the composition of matter has a structure selected from the group consisting of:
14. The composition of matter of claim 13 , wherein the composition of matter has the structure:
15. The composition of matter of claim 6 , wherein the composition of matter has a structure selected from the group consisting of:
16. The composition of matter of claim 15 , wherein the composition of matter has the structure:
17. An organic light emitting device comprising:
an anode;
a cathode;
an organic emissive layer, disposed between the anode and the cathode, the organic emissive layer further comprising a host and a phosphorescent dopant,
an organic hole transport layer comprising a hole transport material, disposed between the organic emissive layer and the anode, and in direct contact with the organic emissive layer;
wherein the hole transport material has the structure:
wherein n is 1, 2 or 3, and the phenyl rings between the nitrogen atoms may be attached to each other and to the nitrogen atoms in a para or meta configuration independently selected for each attachment;
wherein each of R 2 , R 3 and R 4 are independently selected from the group consisting of:
wherein R 1 is selected from the group consisting of:
wherein the dotted line shows the point of attachment to an N atom of Formula I:
wherein at least one of R 2 , R 3 and R 4 is selected from the group consisting of:
wherein each of R 1 , R 2 , R 3 and R 4 may be further substituted with substituents that are not fused to R 1 , R 2 , R 3 and R 4 ,
wherein the dotted line shows the point of attachment to an N atom of Formula I;
wherein at least one of R 2 , R 3 , and R 4 is selected from the group consisting of:
wherein each of R 1 , R 2 , R 3 , and R 4 may be further substituted with substituents that are not fused to R 1 , R 2 , R 3 , and R 4 .
18. The device of claim 17 , wherein the dopant is an organo-metallic iridium material.
19. The device of claim 17 , wherein at least one of R 2 , R 3 , and R 4 is
20. The device of claim 19 , wherein the host is a compound comprising a triphenylene containing benzo-fused thiophene.
21. A consumer product, wherein the consumer product includes an organic light emitting device that further includes a composition of matter having the chemical structure:
wherein n is 1, 2 or 3, and the phenyl rings between the nitrogen atoms may be attached to each other and to the nitrogen atoms in a para or meta configuration independently selected for each attachment;
wherein each of R 2 , R 3 and R 4 are independently selected from the group consisting of:
wherein R 1 is selected from the group consisting of:
wherein the dotted line shows the point of attachment to an N atom of Formula I;
wherein at least one of R 2 , R 3 and R 4 is selected from the group consisting of:
wherein each of R 1 , R 2 , R 3 and R 4 may be further substituted with substituents that are not fused to R 1 , R 2 , R 3 and R 4 .