Compound, material for organic electroluminescence elements, organic electroluminescence element, and electronic device

1. A compound represented by formula (1):

wherein:

each of R 1 to R 3 is independently one selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 50 ring carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a haloalkoxy group having 1 to 20 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, an aryloxy group having 6 to 18 ring carbon atoms, a halogen atom, and a cyano group;

each of R 4 and R 5 is independently one selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 50 ring carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a haloalkoxy group having 1 to 20 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, an aryloxy group having 6 to 18 ring carbon atoms, a halogen atom, and a cyano group;

a is an integer of 0 to 4;

b is an integer of 0 to 2;

c is an integer of 0 to 3;

d is an integer of 0 to 3;

e is an integer of 0 to 4;

each of (R 1 ) 0 , (R 2 ) 0 , (R 3 ) 0 , (R 4 ) 0 , and (R 5 ) 0 respectively mean that R 1 , R 2 , R 3 , R 4 or R 5 is not present;

when a, b, c, d, or e is an integer of 2 or more, two to four R 1 's, two R 2 's, two or three R 3 's, two or three R 4 's, and two to four R 5 's may be the same or different, respectively; and adjacent two selected from R 1 to R 5 are not bonded to each other, thereby failing to form a ring structure;

L1 is a single bond or an arylene group represented by formula (ii) or (iii):

wherein in formulae (ii) and (iii):

each R is independently one selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, a cycloalkyl group having 3 to 50 ring carbon atoms, an aralkyl group having 7 to 30 carbon atom which includes an aryl group having 6 to 18 ring carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 18 ring carbon atoms, a mono-, di-, or tri-substituted silyl group including a substituent selected from an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 18 ring carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a haloalkoxy group having 1 to 20 carbon atoms, a halogen atom, a cyano group, and a nitro group;

each q is independently an integer of 0 to 4;

(R) 0 means that R is not present;

when q is an integer of 2 or more, two to four Rs, two to three Rs, or two Rs may be the same or different; and

one of ** and *** is a bond to Ar in formula (1), and the other is a bond to the nitrogen atom in formula (1),

L 2 is a single bond or a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms;

L 3 is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms;

Ar is represented by one selected from the group consisting of formulae (a), (b), (d), (e), (f), (g), (h), (i), (j), (k), and (m):

wherein in formulae (a), (b), (d), (e), (f), (g), (h), (i), (j), (k), and (m):

is a bond to L 1 in formulae (1),

R and q are the same as defined with respect to formulae (ii) and (iii);

each p is independently an integer of 0 to 5;

each r is independently an integer of 0 to 3;

s is independently an integer of 0 to 2;

t is independently 0 or 1;

(R) 0 means that R is not present;

when p, q, r or s is an integer of 2 or more, two to five Rs, two to four Rs, two to three Rs, or two Rs may be the same or different;

each of R a and R b of formula (g) is independently one selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, a cycloalkyl group having 3 to 50 ring carbon atoms, an aralkyl group having 7 to 30 carbon atom which includes an aryl group having 6 to 18 ring carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 18 ring carbon atoms, a mono-, di-, or tri-substituted silyl group including a substituent selected from an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 18 ring carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a haloalkoxy group having 1 to 20 carbon atoms, a halogen atom, a cyano group, and a nitro group;

Y of formulae (j) and (k) is a nitrogen atom, an oxygen atom, or a sulfur atom; and

adjacent two Rs in formulae (a), (b), (d), (e), and (h) to (j) may be bonded to each other to form a ring structure, two selected from R, R a , and R b of formula (g) may be bonded to each other to form a ring structure, and adjacent two Rs in formulae (f), (k), and (m) are not bonded to each other, thereby failing to form a ring structure,

provided that when Ar is represented by formula (a) or (b), L 1 is a single bond;

X is an oxygen atom or a sulfur atom; and

an optional substituent referred to by “substituted or unsubstituted” is one selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, a cycloalkyl group having 3 to 50 ring carbon atoms, an aralkyl group having 7 to 30 carbon atom which includes an aryl group having 6 to 18 ring carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 18 ring carbon atoms, a mono-, di-, or tri-substituted silyl group including a substituent selected from an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 18 ring carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a haloalkoxy group having 1 to 20 carbon atoms, a halogen atom, a cyano group, and a nitro group, and two or more optional groups, if present, may be the same or different.

2. The compound according to claim 1 , wherein the compound is represented by formula (2):

wherein R 1 to R 5 , a to e, L 1 to L 3 , Ar, and X are as defined in formula (1).

3. The compound according to claim 1 , wherein the compound is represented by formula (3):

wherein R 1 to R 5 , a to e, L 1 to L 3 , Ar, and X are as defined in formula (1).

4. The compound according to claim 1 , wherein the compound is represented by formula (4):

wherein R 1 to R 5 , a to e, L 1 to L 3 , Ar, and X are as defined in formula (1).

5. The compound according to claim 1 , wherein the compound is represented by formula (5):

wherein R 1 to R 5 , a to e, L 1 to L 3 , Ar, and X are as defined in formula (1).

6. The compound according to claim 1 , wherein:

when Ar is represented by formula (a), (b) or (d), L 1 is a single bond.

7. The compound according to claim 1 , wherein:

Ar is represented by one selected from the group consisting of formulae (a), (b), (e), (f), (g), (h), (i), (j), (k), and (m).

8. The compound according to claim 1 , wherein:

Ar is represented by one selected from the group consisting of formulae (a), (b), (e), (f), (g), (h), and (i).

9. The compound according to claim 1 , wherein Ar is represented by any of formulae (b-1), (b-2), (b-3), (d-1), (d-2), (d-3), (e-1), (1), (g-1), (i-1), (i-2), (m-1), and (m-2):

wherein:

R, q, r, s, and * of formulae (b-1), (b-2), (b-3), (d-1), (d-2), (d-3), (e-1), (f), (g-1), (i-1), (i-2), (m-1), and (m-2) are the same as defined with respect to formulae (a), (b), (d), (e), (f), (g), (h), (i), (j), (k), and (m);

(R) 0 means that R is not present;

when q, r or s is an integer of 2 or more, two to five Rs, two to four Rs, two to three Rs, or two Rs may be the same or different; and

provided that adjacent two Rs in each of the above formulae are not bonded to each other, thereby failing to form a ring structure.

10. The compound according to claim 1 , wherein the arylene group having 6 to 30 ring carbon atoms for L 2 and L 3 is one selected from the group consisting of divalent groups obtained by removing one hydrogen atom from a phenyl group, a biphenylyl group, a terphenylyl group, a biphenylenyl group, a naphthyl group, an acenaphthylenyl group, an anthryl group, a benzanthryl group, an aceanthryl group, a 2-phenanthryl group, a benzophenanthryl group, a triphenylenyl group, a phenalenyl group, a fluorenyl group, a benzofluorenyl group, a 9,9′-spirobifluorenyl group, a pentacenyl group, a picenyl group, a pentaphenyl group, a pyrenyl group, a chrysenyl group, a benzochrysenyl group, a s-indacenyl group, an as-indacenyl group, a fluoranthenyl group, and a perylenyl group.

11. The compound according to claim 1 , wherein L 2 is a single bond or an arylene group represented by formula (ii) or (iii):

wherein:

R and q are the same as defined with respect to formulae (ii) and (iii) for L 1 ; and

one of ** and *** is a bond to the dibenzofuran ring or the dibenzothiophene ring in formula (1), and the other is a bond to the nitrogen atom in formula (1).

12. The compound according to claim 1 , wherein L 3 is an arylene group represented by formula (ii) or (iii):

wherein:

R and q are the same as defined with respect to formulae (ii) and (iii) for L 1 ,

(R) 0 means that R is not present;

when q is an integer of 2 or more, two to four Rs, two to three Rs, or two Rs may be the same or different; and

one of ** and *** is a bond to the 2-phenanthryl group in formula (1), and the other is a bond to the nitrogen atom in formula (1).

13. The compound according to claim 3 , wherein:

Ar is a group represented by formula (b-1), (b-2), (b-3), (c 1), (c 2), (c 3), (d-1), (d-3), (f), (g-1), (i-1), or (i-2);

L 1 is a single bond;

L 2 is a group represented by formula (ii); and

L 3 is a group represented by formula (ii) or (iii).

14. The compound according to claim 3 , wherein:

Ar is a group represented by formula (b-1), (b-2), or (g-1);

L 1 is a single bond; and

each of L 2 and L 3 is a group represented by formula (ii).

15. The compound according to claim 3 , wherein:

Ar is a group represented by formula (d-2), (e-1), (f), (m-1), or (m-2);

each of L 1 and L 2 is a group represented by formula (ii); and

L 3 is a single bond group represented by formula (ii) or (iii).

16. The compound according to claim 3 , wherein:

Ar is a group represented by formula (b-1) or (f);

each of L 2 and L 3 is a group represented by formula (ii); and

L 1 is a single bond.

17. The compound according to claim 11 , wherein the group represented by formula (ii) is a p-phenylene group.

18. The compound according to claim 1 , wherein:

each of R 4 and R 5 is independently an aryl group having 6 to 18 ring carbon atoms; and

the aryl group in the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms for R 4 and R 5 is a phenyl group or a biphenylyl group.

19. A material for organic electroluminescence devices, the material comprising the compound according to claim 1 .

20. An organic electroluminescence device, comprising:

a cathode;

an anode; and

an organic thin film layer disposed between the cathode and the anode,

wherein:

the organic thin film layer comprises one or more layers;

the organic thin film layer comprises a light emitting layer; and

at least one layer of the organic thin film layer comprises the compound according to claim 1 .

21. The organic electroluminescence device according to claim 20 , wherein:

the organic electroluminescence device comprises a hole transporting layer between the anode and the light emitting layer; and

the hole transporting layer comprises the compound.

22. The organic electroluminescence device according to claim 20 , wherein:

the organic electroluminescence device comprises an electron blocking layer between the anode and the light emitting layer; and

the electron blocking layer comprises the compound.

23. The organic electroluminescence device according to claim 20 , wherein:

the organic electroluminescence device comprises an exciton blocking layer between the anode and the light emitting layer; and

the exciton blocking layer comprises the compound.

24. The organic electroluminescence device according to claim 20 , wherein:

the organic electroluminescence device comprises an anode-side organic thin film layer between the anode and the light emitting layer;

the anode-side organic thin film layer comprises one or more layers; and

at least one layer of the anode-side organic thin film layer comprises the compound.

25. The organic electroluminescence device according to claim 24 , wherein:

two or more layers of the anode-side organic thin film layer are hole transporting layers; and

a hole transporting layer closest to the light emitting layer comprises the compound.

26. An electronic device, comprising the organic electroluminescence device according to claim 20 .

27. The compound according to claim 1 , wherein each q in formulae (ii) and (iii) for L 1 is independently an integer of 0 or 1.

28. The compound according to claim 1 , wherein R in formulae (ii) and (iii) for L 1 is independently one selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 50 ring carbon atoms, an aralkyl group having 7 to 30 carbon atom which includes an aryl group having 6 to 18 ring carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 18 ring carbon atoms, a mono-, di-, or tri-substituted silyl group including a substituent selected from an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 18 ring carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a haloalkoxy group having 1 to 20 carbon atoms, a halogen atom, a cyano group, and a nitro group.

29. The compound according to claim 1 , wherein

L 1 is a single bond or an arylene group represented by formula (ii) or (iii):

wherein in formulae (ii) and (iii):

one of ** and *** is a bond to Ar in formula (1), and the other is a bond to the nitrogen atom in formula (1),

provided that when Ar is represented by formula (a), (b), or (d), L 1 is a single bond.