Phenylcarbazole compounds and organic electroluminescence devices using the same
View Patent ↗A phenylcarbazole compound of formula (1) below is provided, where each of R 1 and R 2 is independently a monosubstituted or polysubstituted functional group selected from the group consisting of hydrogen atom, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 4 -C 30 heterocyclic group, a substituted or unsubstituted C 6 -C 30 condensed polycyclic group, wherein groups adjacent to R 1 and R 2 bind and form a saturated or unsaturated cyclic hydrocarbon group, and Ar is a substituted or unsubstituted C 6 -C 30 aryl group or a C 6 -C 30 heteroaryl group, wherein the substituent R 4 is defined herein. Also included is an organic electroluminescence device comprising the above phenylcarbazole compounds.
1. A phenylcarbazole compound of formula (1) below:
wherein each of R 1 and R 2 is independently a hydrogen atom or a monosubstituted or polysubstituted functional group selected from the group consisting of a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 4 -C 30 heterocyclic group, a substituted or unsubstituted C 6 -C 30 condensed polycyclic group, wherein groups adjacent to R 1 and R 2 can bind and form a saturated or unsaturated cyclic hydrocarbon group,
Ar is a phenyl group, a lower alkylphenyl group, a lower alkoxyphenyl group, a phenoxyphenyl group, a halophenyl group, a cyanophenyl group, a dicyanophenyl group, a (α,α-dimethylbenzene)phenyl group, a (N,N′-dimethyl)aminophenyl group, a (N,N′- diphenyl)aminophenyl group, a pentalenyl group, a indenyl group, a naphthyl group, a lower alkylnaphthyl group, a lower alkoxynaphthyl group a cyanonaphthyl group, a halonaphthyl group, an anthracenyl group, an azulenyl group, a heptalenyl group, an acenaphthylenyl group, a fluorenyl group, an anthraquinoyl group, a methylanthryl group, a phenanthryl group, a triphenylene group, a pyrenyl group, a chrysenyl group, an ethyl chrysenyl group, a picenyl group, a chloroperylenyl group, a pentaphenyl group, a pentacenyl group, a tetraphenylenyl group, a hexaphenyl group, a hexacenyl group, a rubicenyl group, a coronenyl group, a trinaphthylenyl group, a heptaphenyl group, a heptacenyl group, a phenanthrenyl group, a ovalenyl group, carbazoyl, lower alkyl carbazoly, biphenyl, lower alkylbiphenyl, lower alkoxybiphenyl, thiophenyl, indoyl or pyrridyl group, and
R 4 is a hydrogen atom or has formula (2) below,
where R 3 is a monosubstituted or polysubstituted functional group selected from the group consisting of a hydrogen atom, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 4 -C 30 heterocyclic group, and a substituted or unsubstituted C 6 -C 30 condensed polycyclic group; and Ar is a substituted or unsubstituted C 6 -C 30 aryl group or a C 6 -C 30 heteroaryl group.
2. The phenylcarbazole compound of claim 1 having the formula (3) below:
wherein each of R 1 , and R 2 , is independently a hydrogen atom or a monosubstituted or polysubstituted functional group selected from the group consisting of a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 4 -C 30 heterocyclic group, a substituted or unsubstituted C 6 -C 30 condensed polycyclic group, wherein groups adjacent to R 1 , R 2 , and R 3 can bind and form a saturated or unsaturated cyclic hydrocarbon group.
3. The phenylcarbazole compound of claim 1 having the formula (4) below:
wherein each of R 1 , R 2 , and R 3 is independently a hydrogen atom or a monosubstituted or polysubstituted functional group selected from the group consisting of a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 4 -C 30 heterocyclic group, a substituted or unsubstituted C 6 -C 30 condensed polycyclic group, wherein groups adjacent to R 1 , R 2 , and R 3 can bind and form a saturated or unsaturated cyclic hydrocarbon group.
4. The phenylcarbazole compound of claim 1 , having the structure of formula (5) below:
5. The phenylcarbazole compound of claim 1 , wherein each of R 1 , R 2 , and R 3 may be a substituted or unsubstituted C 6 -C 30 aryl group independently selected from the group consisting of a phenyl group, a lower alkylphenyl group, a lower alkoxyphenyl group, a cyanophenyl group, a phenoxyphenyl group, a halophenyl group, a naphthyl group, a lower alkylnaphthyl group, a lower alkoxynaphthyl group, a cyanonaphthyl group, a halonaphthyl group, a fluorenyl group, a carbazoyl group, a lower alkyl carbazoyl group, a biphenyl group, a lower alkylbiphenyl group, a lower alkoxybiphenyl group, a thiophenyl group, an indoyl group, a pyrridyl group, and a phenanthrenyl group.
6. The phenylcarbazole compound of claim 5 , wherein the Ar can be selected from the group consisting of a phenyl group, a lower alkylphenyl group, a lower alkoxyphenyl group, a cyanophenyl group, a phenoxyphenyl group, a halophenyl group, a naphthyl group, a lower alkylnaphthyl group, a lower alkoxynaphthyl group, a cyanonaphthyl group, a halonaphthyl group, a fluorenyl group, a carbazoyl group, a lower alkyl carbazoyl group, a biphenyl group, a lower alkylbiphenyl group, a lower alkoxybiphenyl group, a thiophenyl group, an indoyl group, a pyrridyl group, and a phenanthrenyl group.
7. The phenylcarbazole compound of claim 1 , wherein Ar may be selected from the group consisting of a fluorenyl group, a carbazoyl group, a phenyl group, a naphthyl group, and a phenanthrenyl group.
8. The phenylcarbazole compound of claim 1 , wherein the compound is
9. An organic electroluminescence device comprising:
a pair of electrodes; and
an organic layer containing the phenylcarbazole compound according to claim 1 .
10. An organic electroluminescence device comprising:
a pair of electrodes; and
an organic layer containing the phenylcarbazole compound according to claim 2 .
11. An organic electroluminescence device comprising:
a pair of electrodes; and
an organic layer containing the phenylcarbazole compound according to claim 3 .
12. An organic electroluminescence device comprising:
a pair of electrodes; and
an organic layer containing the phenylcarbazole compound according to claim 4 .
13. An organic electroluminescence device comprising:
a pair of electrodes; and
an organic layer containing the phenylcarbazole compound according to claim 5 .
14. An organic electroluminescence device comprising:
a pair of electrodes; and
an organic layer containing the phenylcarbazole compound according to claim 6 .
15. An organic electroluminescence device comprising:
a pair of electrodes; and
an organic layer containing the phenylcarbazole compound according to claim 7 .
16. The organic electroluminescence device of claim 9 , wherein the organic layer is an emitting layer.
17. The organic electroluminescence device of claim 9 , wherein the organic layer further includes at least one selected from among a hole injecting layer, a hole transporting layer, an electron injecting layer, an electron transporting layer, and a hole blocking layer.
18. The organic electroluminescence device of claim 9 , wherein the organic layer is a hole injecting layer or a hole transporting layer.
19. The organic electroluminescence device of claim 9 , wherein the emitting layer contains blue, green, and red dopants.
20. The organic electroluminescence device of claim 12 , wherein the amount of the blue, green, and red dopants in the emitting layer is in a range of about 0.1 to about 10 parts by weight based on 100 parts by weight of the phenylcarbazole compound.