Organic electroluminescence element and electronic device

1. An organic electroluminescence device, comprising:

a cathode,

an anode, and

an organic layer disposed between the cathode and the anode,

wherein the organic layer comprises a layer that comprises a fluorescent emitting layer and

the fluorescent emitting layer comprises from 1 to 10% by mass of a first compound selected from the group consisting of formula (1-1), formula (1-2), formula (1-3), formula (2-2) and formula (2-5) as a light emitting dopant material and a second compound that is not the same as the first compound:

wherein

R 1 to R 4 and R 6 to R 11 are each independently a hydrogen atom or a substituent, when any of R 1 to R 4 and R 6 to R 11 is the substituent, the substituent is independently a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, an amino group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, a group of —Si(R 101 )(R 102 )(R 103 ), a group of —N(R 104 )(R 105 ), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, wherein R 101 to R 105 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms;

adjacent two selected from R 1 to R 3 are bonded to each other to form a ring structure or not bonded to each other thereby failing to form a ring;

adjacent two selected from R 6 to R 7 are bonded to each other to form a ring structure or not bonded to each other thereby failing to form a ring; and

adjacent two selected from R 8 to R 11 are bonded to each other to form a ring structure or not bonded to each other thereby failing to form a ring

each of rings a, b and e to h is independently a ring structure having 3 or more atoms selected from the group consisting of carbon, oxygen, sulfur, nitrogen and combinations thereof;

the ring structure optionally has a substituent and the substituents are optionally bonded to each other to form a ring structure;

the substituent is the same as defined with respect to the substituent of R 1 to R 4 and R 6 to R 11 ; and

the number of atoms of the ring structure having 3 or more atoms does not include the atom in the substituent.

2. The organic electroluminescence device according to claim 1 , wherein the substituent of the rings a, b and e to f is independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a group of —N(R 104 )(R 105 ), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, or any of the following groups:

wherein:

X is selected from the group consisting of C(R 23 )(R 24 ), NR 25 , O, and S;

R 104 to R 105 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms;

each R c and R 23 to R 25 are independently the same as R 1 to R 4 and R 6 to R 11 ;

adjacent groups selected from R 23 to R 24 are optionally bonded to each other to form a ring structure; and

p1 is an integer of 0 to 5, p2 is an integer of 0 to 4, p3 is an integer of 0 to 3, and p4 is an integer of 0 to 7.

3. The organic electroluminescence device according to claim 1 , wherein the substituent of the rings g and h is independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or any of the following groups:

wherein:

each R c is independently the same as R 1 to R 4 and R 6 to R 11 ; and

p1 is an integer of 0 to 5, p2 is an integer of 0 to 4, and p4 is an integer of 0 to 7.

4. The organic electroluminescence device according to claim 1 , wherein the first compound is a compound of any of formula (4-1) to (4-3):

wherein:

R 1 to R 5 , R 7 to R 11 , and R 41 to R 48 , are the same as R 1 to R 4 and R 6 to R 11 .

5. The organic electroluminescence device according to claim 1 , wherein R 1 to R 3 are each a hydrogen atom or a substituent, when any of R 1 to R 3 is the substituent, the substituent is independently a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, an amino group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, a group of —Si(R 101 )(R 102 )(R 103 ), a group of —N(R 104 ) (R 105 ), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.

6. The organic electroluminescence device according to claim 1 ,

wherein R 2 is a group not forming the ring structure having 3 or more atoms and is a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, an amino group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, a group of —Si(R 101 )(R 102 )(R 103 ), a group of —N(R 104 ) (R 105 ), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.

7. The organic electroluminescence device according to claim 1 ,

wherein the second compound is a compound comprising a polycyclic aromatic skeleton.

8. The organic electroluminescence device according to claim 1 ,

wherein the second compound is a compound comprising a fused polycyclic aromatic skeleton.

9. The organic electroluminescence device according to claim 1 ,

wherein the second compound comprises a fused polycyclic aromatic skeleton that comprises 3 or more fused rings.

10. The organic electroluminescence device according to claim 1 ,

wherein the second compound is a compound comprising an anthracene skeleton, a compound comprising a chrysene skeleton, a compound comprising a pyrene skeleton, or a compound comprising a fluorene skeleton.

11. The organic electroluminescence device according to claim 10 , wherein the second compound is a compound comprising an anthracene skeleton and the compound comprising an anthracene skeleton is of formula (19):

wherein:

R 101 to R 110 are each independently a hydrogen atom or a substituent, wherein the substituent is independently a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, an amino group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, a group represented by —Si(R 101 )(R 102 )(R 103 ), a group represented by —N(R:04) (R 105 ), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, or —L—Ar, provided that at least one of R 101 to R 110 is —L—Ar,

each L is independently selected from a single bond and a linking group, wherein the linking group is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms; and

each Ar is independently a substituted or unsubstituted single ring group having 5 to 50 ring atoms, a substituted or unsubstituted fused ring group having 8 to 50 ring atoms, or a group wherein the single ring group and the fused ring group are linked to each other.

12. The organic electroluminescence device according to claim 11 , wherein

the compound comprising an anthracene skeleton is of formula (20):

wherein:

R 101 to R 108 are each independently a hydrogen atom or a substituent, wherein the substituent is independently a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, an amino group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, a group represented by —Si(R 101 )(R 102 )(R 103 ), a group represented by —N(R 104 ) (R 105 ), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms;

Ar 11 and Ar 12 are each independently a substituted or unsubstituted single ring group having 5 to 50 ring atoms, a substituted or unsubstituted fused ring group having 8 to 50 ring atoms, or a group wherein the single ring group and the fused ring group are linked to each other; and

each L 1 is independently selected from a single bond and a linking group, wherein the linking group is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms.

13. The organic electroluminescence device according to claim 10 , wherein the second compound is a compound comprising a chrysene skeleton and the compound comprising a chrysene skeleton is of formula (21):

wherein:

R 201 to R 212 are each independently a hydrogen atom or a substituent, wherein the substituent is independently a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, an amino group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, a group represented by —Si(R 101 )(R 102 )(R 103 ), a group represented by —N(R 104 )(R 105 ), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, or —L 2 —Ar 21 , provided that at least one of R 201 to R 212 is —L 2 —Ar 21 ;

each L 2 is independently selected from a single bond and a linking group, wherein the linking group is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms; and

each Ar 21 is independently a substituted or unsubstituted single ring group having 5 to 50 ring atoms, a substituted or unsubstituted fused ring group having 8 to 50 ring atoms, or a group wherein the single ring group and the fused ring group are linked to each other.

14. The organic electroluminescence device according to claim 10 , wherein the second compound is a compound comprising a pyrene skeleton and the compound comprising a pyrene skeleton is a compound of formula (22):

wherein:

R 301 to R 310 are each independently a hydrogen atom or a substituent, wherein the substituent is independently a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, an amino group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, a group represented by —Si(R 101 )(R 102 )(R 103 ), a group represented by —N(R 104 )(R 105 ), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms or —L 3 —Ar 31 , provided that at least one of R 301 to R 310 is —L 3 —Ar 31 ;

each L 3 is independently selected from a single bond and a linking group, wherein the linking group is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms; and

each Ar 31 is independently a substituted or unsubstituted single ring group having 5 to 50 ring atoms, a substituted or unsubstituted fused ring group having 8 to 50 ring atoms, or a group wherein the single ring group and the fused ring group are linked to each other.

15. The organic electroluminescence device according to claim 10 , wherein the second compound is a compound comprising a fluorene skeleton and the compound comprising a fluorene skeleton is a compound of formula (23):

wherein:

R 401 to R 410 are each independently a hydrogen or a substituent, wherein the substituent is independently a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, an amino group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, a group represented by —Si(R 101 )(R 102 )(R 103 ), a group represented by —N(R 104 ) (R 105 ), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, or —L 4 —Ar 41 , provided that at least one of R 401 to R 410 is —L 4 —Ar 41 ;

each L 4 is independently selected from a single bond and a linking group, wherein the linking group is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms,

each Ar 41 is independently a substituted or unsubstituted single ring group having 5 to 50 ring atoms, a substituted or unsubstituted fused ring group having 8 to 50 ring atoms, or a group wherein the single ring group and the fused ring group are linked to each other; and

one or more pairs selected from R 401 and R 402 , R 402 and R 403 , R 403 and R 404 , R 405 and R 406 R 406 and R 407 , and R 407 and R 408 are optionally bonded to each other to form a ring.

16. The organic electroluminescence device according to claim 1 , wherein the fluorescent emitting layer does not contain a heavy metal complex.

17. An electronic device, comprising the organic electroluminescence device of claim 1 .