Organic electroluminescence device and novel compound
An organic electroluminescence device comprising: a cathode, an anode, and at least one organic layer disposed between the cathode and the anode, wherein at least one layer of the at least one organic layer comprises a compound represented by the following formulas (1-1) and (1-3) or a compound represented by the following formulas (1-2) and (1-3).
1. An organic electroluminescence device, comprising:
a cathode,
an anode, and
at least one organic layer arranged between the cathode and the anode, wherein
at least one layer of the at least one organic layer is an emitting layer,
an electron-transporting zone is provided between the cathode and the emitting layer,
the emitting layer comprises a compound represented by the following formula (3-12), and
the electron-transporting zone comprises an aromatic heterocyclic compound:
wherein in the formula (3-12),
one or more pairs of adjacent two or more of R 1 to R 7 and R 10 to R 16 may form a substituted or unsubstituted, saturated or unsaturated ring;
R 1 to R 7 , and R 10 to R 16 that do not form the substituted or unsubstituted, saturated or unsaturated ring and R 17 are independently a hydrogen atom, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms, provided that at least two of R 1 to R 7 and R 10 to R 16 are —N(R 36 )(R 37 );
two R 17 s may be the same or different;
R 36 and R 37 are independently a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;
a substituent in the “substituted or unsubstituted” is selected from the group consisting of an alkyl group including 1 to 50 carbon atoms, a haloalkyl group including 1 to 50 carbon atoms, a alkenyl group including 2 to 50 carbon atoms, a alkynyl group including 2 to 50 carbon atoms, a cycloalkyl group including 3 to 50 ring carbon atoms, a alkoxy group including 1 to 50 carbon atoms, a alkylthio group including 1 to 50 carbon atoms, a aryloxy group including 6 to 50 ring carbon atoms, a arylthio group including 6 to 50 ring carbon atoms, a aralkyl group including 7 to 50 carbon atoms, —Si(R 41 )(R 42 )(R 43 ), —C(═O)R 44 , —COOR 45 , —S(═O) 2 R 46 , —P(═O)(R 47 )(R 48 ), —Ge(R 49 )(R 50 )(R 51 ), —N(R 52 )(R 53 ), a hydroxyl group, a halogen atom, a cyano group, a nitro group, an aryl group including 6 to 50 ring carbon atoms, and a monovalent heterocyclic group including 5 to 50 ring atoms;
R 41 to R 53 are independently a hydrogen atom, an alkyl group including 1 to 50 carbon atoms, an aryl group including 6 to 50 ring carbon atoms or a monovalent heterocyclic group including 5 to 50 ring atoms;
when each of R 41 s to R 53 s are present in plural, each of the plural R 41 s to R 53 s may be the same or different; and
one or more pairs of adjacent two or more of the substituent in the “substituted or unsubstituted” do not form a substituted or unsubstituted, saturated or unsaturated ring.
2. The organic electroluminescence device according to claim 1 , wherein in the formula (3-12), any one couple selected from R 2 and R 11 , R 4 and R 13 , and R 5 and R 14 are both —N(R 36 )(R 37 ).
3. The organic electroluminescence device according to claim 1 , wherein the compound represented by the formula (3-12) is the compound represented by the following formula (3-21), (3-33) or (3-34):
wherein in the formula (3-21),
one or more pairs of adjacent two or more of R 1 to R 4 and R 10 to R 13 may form a substituted or unsubstituted, saturated or unsaturated ring;
R 1 to R 4 and R 10 to R 13 that do not form the substituted or unsubstituted, saturated or unsaturated ring and R 17 are independently a hydrogen atom, a substituted or unsubstituted aryl group including 6 to 20 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group including 5 to 20 ring atoms;
two R 17 s may be the same or different;
R A , R B , R C and R D are independently a substituted or unsubstituted aryl group including 6 to 20 ring carbon atoms;
wherein in the formulas (3-33) and (3-34); R 5 to R 7 and R 14 to R 17 are independently a hydrogen atom, a substituted or unsubstituted aryl group including 6 to 20 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group including 5 to 20 ring atoms, two R 17 s may be the same or different; and
Ar 1 to Ar 4 are independently a substituted or unsubstituted aryl group including 6 to 20 ring carbon atoms.
4. The organic electroluminescence device according to claim 3 , wherein the compound represented by the formula (3-21) is the compound represented by the following formula (3-22):
wherein in the formula (3-22), R 17 , R A , R B , R C and R D are as defined in the formula (3-21).
5. The organic electroluminescence device according to claim 3 , wherein in the compound represented by the formula (3-33) or (3-34), R 5 to R 7 and R 14 to R 16 are a hydrogen atom.
6. The organic electroluminescence device according to claim 3 , wherein R A , R B , R C and R D in the formula (3-21) or Ar 1 to Ar 4 in the formula (3-33) and the formula (3-34) are independently a substituted or unsubstituted phenyl group.
7. The organic electroluminescence device according to claim 1 , wherein two R 17 s are a hydrogen atom.
8. The organic electroluminescence device according to claim 3 , wherein the substituent in the “substituted or unsubstituted” is selected from the group consisting of an alkyl group including 1 to 20 carbon atoms, an aryl group including 6 to 20 ring carbon atoms and a monovalent heterocyclic group including 5 to 20 ring atoms.
9. The organic electroluminescence device according to claim 3 , wherein the substituent in the “substituted or unsubstituted” is an alkyl group including 1 to 5 carbon atoms.
10. The organic electroluminescence device according to claim 3 , wherein R A , R B , R C and R D in the formula (3-21) or Ar 1 to Ar 4 in the formula (3-33) and the formula (3-34) are independently a substituted or unsubstituted phenyl group; and
two R 17 s are independently a hydrogen atom.
11. The organic electroluminescence device according to claim 3 , wherein R A , R B , R C and R D in the formula (3-21) or Ar 1 to Ar 4 in the formula (3-33) and the formula (3-34) are independently a substituted or unsubstituted phenyl group;
two R 17 s are independently a hydrogen atom; and
the substituent in the “substituted or unsubstituted” is selected from the group consisting of an alkyl group including 1 to 20 carbon atoms, an aryl group including 6 to 20 ring carbon atoms and a monovalent heterocyclic group including 5 to 20 ring atoms.
12. The organic electroluminescence device according to claim 3 , wherein R A , R B , R C and R D the formula (3-21) or Ar 1 to Ar 4 in the formula (3-33) and the formula (3-34) are independently a substituted or unsubstituted phenyl group;
two R 17 s are independently a hydrogen atom; and
the substituent in the “substituted or unsubstituted” is an alkyl group including 1 to 5 carbon atoms.
13. The organic electroluminescence device according to claim 1 , wherein one of R 36 and R 37 is a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, and the other of R 36 and R 37 is a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms.
14. The organic electroluminescence device according to claim 1 , wherein at least one of R 36 and R 37 is a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group or a substituted or unsubstituted indolocarbazolyl group.
15. The organic electroluminescence device according to claim 1 , wherein at least one of R 36 and R 37 is a substituted or unsubstituted dibenzofuranyl group.
16. The organic electroluminescence device according to claim 1 , wherein R 1 to R 7 and R 10 to R 16 are hydrogen atoms.
17. The organic electroluminescence device according to claim 1 , wherein the emitting layer comprises one or more compounds selected from the group consisting of the compound represented by the following formula (BD-4) and the compound represented by the following formula (BD-9):
18. The organic electroluminescence device according to claim 1 , wherein the emitting layer comprises one or more compounds selected from the group consisting of the compound represented by the following formula (BD-4) and the compound represented by the following formula (BD-9), and the electron-transporting zone comprises the compound represented by the following formula (ET):
19. The organic electroluminescence device according to claim 1 , wherein the electron-transporting zone comprises an electron-injecting layer, and the electron-injecting layer comprises the aromatic heterocyclic compound.
20. The organic electroluminescence device according to claim 1 , wherein the aromatic heterocyclic compound is a benzimidazole derivative.
21. The organic electroluminescence device according to claim 1 , wherein the aromatic heterocyclic compound is a compound represented by the following formula (ET):
22. An electronic apparatus provided with the organic electroluminescence device according to claim 1 .