Compound for use in organic electroluminescent device and organic electroluminescent device
View Patent ↗Disclosed are an organic electroluminescent device (organic EL device) which is improved in luminous efficiency, fully secured of driving stability, and simple in constitution and a compound for use therein. The organic electroluminescent device comprises a light-emitting layer disposed between an anode and a cathode piled one upon another on a substrate and the light-emitting layer contains a phosphorescent dopant and a compound for use in an organic electroluminescent device having two or more indolocarbazole skeletons as a host material. An example of the compound having indolocarbazole skeletons for use in the device is expressed by the following formula.
1. A compound for use in an organic electroluminescent device represented by the following general formula (1):
Z Y) n (1)
wherein, Z is a linking group consisting of a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group, Y is a group represented by the following general formula (1a), and n is an integer of 2 or greater;
wherein, ring A is an aromatic or heterocyclic ring condensed with the adjacent rings and represented by formula (1b), ring B is a heterocyclic ring condensed with the adjacent rings and represented by formula (1c), X is carbon or nitrogen, R 43 is hydrogen, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a ring condensed with the X-containing ring, R 44 is a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group, and each of R 41 and R 42 is hydrogen, an alkyl group, an aralkyl group, an alkenyl group, an alkynyl group, a cyano group, a dialkylamino group, a diarylamino group, a diaralkylamino group, an amino group, a nitro group, an acyl group, an alkoxycarbonyl group, a carboxyl group, an alkoxyl group, an alkylsulfonyl group, a haloalkyl group, a hydroxyl group, an amide group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group.
2. A compound for use in an organic electroluminescent device as described in claim 1 wherein Y in general formula (1) is a group represented by general formula (1d):
wherein, R 45 has the same meaning as R 43 , R 46 has the same meaning as R 44 , and each of R 47 and R 48 independently has the same meaning as R 41 .
3. A compound for use in an organic electroluminescent device as described in claim 1 wherein n is 3 or 4 in general formula (1).
4. An organic electroluminescent device comprising a light-emitting layer disposed between an anode and a cathode piled one upon another on a substrate wherein the light-emitting layer contains a phosphorescent dopant and the compound for use in an organic electroluminescent device described in claim 1 as a host material.
5. An organic electroluminescent device as described in claim 4 wherein a hole-injecting/transporting layer is disposed between the anode and the light-emitting layer and an electron-injecting/transporting layer is disposed between the cathode and the light-emitting layer.
6. An organic electroluminescent device as described in claim 5 wherein a hole-blocking layer is disposed between the light-emitting layer and the electron-injecting/transporting layer.
7. A compound for use in an organic electroluminescent device as described in claim 1 wherein the compound is represented by the following general formula (2) or (3):
wherein, each of ring A and ring A′ is an aromatic or heterocyclic ring condensed with the adjacent rings and represented by formula (2a), each of ring B and ring B′ is a heterocyclic ring condensed with the adjacent rings and represented by formula (2b), Ar 1 is a divalent linking group consisting of a non-condensed substituted or unsubstituted aromatic hydrocarbon group or a non-condensed substituted or unsubstituted aromatic heterocyclic group, X is carbon or nitrogen, R 5 is a non-condensed substituted or unsubstituted aromatic hydrocarbon group or a non-condensed substituted or unsubstituted aromatic heterocyclic group, and each of R 1 to R 4 is independently hydrogen, an alkyl group, an aralkyl group, an alkenyl group, an alkynyl group, a cyano group, a dialkylamino group, a diarylamino group, a diaralkylamino group, an amino group, a nitro group, an acyl group, an alkoxycarbonyl group, a carboxyl group, an alkoxyl group, an alkylsulfonyl group, a haloalkyl group, a hydroxyl group, an amide group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group;
wherein, each of ring C and ring C′ is an aromatic or heterocyclic ring condensed with the adjacent rings and represented by formula (3a), each of ring D and ring D′ is a heterocyclic ring condensed with the adjacent rings and represented by formula (3b), each of ring E and ring E′ is a heterocyclic ring condensed with the adjacent rings and represented by formula (3c), Ar 2 is a divalent linking group consisting of a non-condensed substituted or unsubstituted aromatic hydrocarbon group or a non-condensed substituted or unsubstituted aromatic heterocyclic group, X is carbon or nitrogen, R 13 has the same meaning as R 5 , each of R 14 and R 15 independently has the same meaning as R 6 , and each of R 7 to R 12 independently has the same meaning as R 1 .
8. A compound for use in an organic electroluminescent device as described in claim 7 wherein each of ring A, ring A′, ring C, and ring C′ is a benzene ring, each of R 6 , R 14 , and R 15 , is a substituted or unsubstituted phenyl or pyridyl group, and each of R 1 to R 4 , and R 7 to R 12 is hydrogen or a phenyl group in general formulas (2) to (3) and formulas (2a), 2(b) and (3a) to (3c).
9. A compound for use in an organic electroluminescent device as described in claim 1 wherein the compound is represented by the following general formula (4) or (5):
wherein, Ar 3 is a divalent linking group consisting of a non-condensed substituted or unsubstituted aromatic hydrocarbon group or a non-condensed substituted or unsubstituted aromatic heterocyclic group, each of R 17 and R 20 is hydrogen, a non-condensed substituted or unsubstituted aromatic hydrocarbon group, or a non-condensed substituted or unsubstituted aromatic heterocyclic group, each of R 22 and R 23 is a non-condensed substituted or unsubstituted aromatic hydrocarbon group or a non-condensed substituted or unsubstituted aromatic heterocyclic group, and each of R 16 , R 18 , R 19 , and R 21 is hydrogen, an alkyl group, an aralkyl group, an alkenyl group, an alkynyl group, a cyano group, a dialkylamino group, a diarylamino group, a diaralkylamino group, an amino group, a nitro group, an acyl group, an alkoxycarbonyl group, a carboxyl group, an alkoxyl group, an alkylsulfonyl group, a haloalkyl group, a hydroxyl group, an amide group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group;
wherein, each of ring F and ring F′ is a heterocyclic ring condensed with the adjacent rings and represented by formula (5a), Ar 4 has the same meaning as Ar 3 , each of R 30 to R 32 independently has the same meaning as R 22 , and each of R 24 to R 29 independently has the same meaning as R 16 .
10. A compound for use in an organic electroluminescent device as described in claim 9 wherein each of R 22 , R 23 , and R 30 to R 32 is a substituted or unsubstituted phenyl or pyridyl group, and each of R 16 to R 21 , and R 24 to R 29 is hydrogen or a phenyl group in general formulas (4), (5) and formula (5a).
11. A compound for use in an organic electroluminescent device represented by the following general formula (1):
Z Y) n (1)
wherein, Z is a linking group consisting of a non-condensed substituted or unsubstituted aromatic hydrocarbon group or a non-condensed substituted or unsubstituted aromatic heterocyclic group, Y is a group represented by the following general formula (1a), and n is an integer of 2 or greater;
wherein, ring A is an aromatic or heterocyclic ring condensed with the adjacent rings and represented by formula (1b), ring B is a heterocyclic ring condensed with the adjacent rings and represented by formula (1c), X is carbon or nitrogen, R 43 is hydrogen, a non-condensed substituted or unsubstituted aromatic hydrocarbon group, a non-condensed substituted or unsubstituted aromatic heterocyclic group, or a ring condensed with the X-containing ring, R 44 is a non-condensed substituted or unsubstituted aromatic hydrocarbon group or a non-condensed substituted or unsubstituted aromatic heterocyclic group, and each of R 41 and R 42 is hydrogen, an alkyl group, an aralkyl group, an alkenyl group, an alkynyl group, a cyano group, a dialkylamino group, a diarylamino group, a diaralkylamino group, an amino group, a nitro group, an acyl group, an alkoxycarbonyl group, a carboxyl group, an alkoxyl group, an alkylsulfonyl group, a haloalkyl group, a hydroxyl group, an amide group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group.
12. A compound for use in an organic electroluminescent device as described in claim 1 , wherein the compound is selected from the group consisting of: