Compound, organic electroluminescence device material, organic electroluminescence device and electronic device
A compound is represented by a formula (1) below. In the formula (1), X 1 to X 8 each independently represent a carbon atom to be bonded to a group represented by the following formula (20), CR X or a nitrogen atom. At least one of X 1 to X 8 is a carbon atom to be bonded to the group represented by the following formula (2). R X is each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or the like.
1. An organic electroluminescence device comprising:
an anode;
a cathode opposed to the anode; and
an organic compound layer provided between the anode and the cathode, the organic compound layer comprising a compound according to formula (1):
where:
one of X 1 to X 8 is a carbon atom bonded to a group according to formula (2);
the rest of X 1 to X 8 are CR x or a nitrogen atom;
R x is not the group according to formula (2); and
each R x is independently selected from the group consisting of:
a hydrogen atom,
a halogen atom,
a cyano group,
a nitro group,
a substituted or unsubstituted hydroxyl group,
a substituted or unsubstituted carboxyl group,
a substituted or unsubstituted sulfonyl group,
a substituted or unsubstituted boryl group,
a substituted or unsubstituted phosphino group,
a substituted or unsubstituted mercapto group,
a substituted or unsubstituted acyl group,
a substituted or unsubstituted amino group,
a substituted or unsubstituted silyl group,
a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,
a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms,
a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, and
a substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms; and
among X 1 to X 8 , adjacent R x of CR x are not bonded to each other;
where:
b is an integer of 1 to 5;
c is an integer of 1 to 8;
Z is an oxygen atom, a sulfur atom, or a silicon atom;
when b is 2 to 5, Z are the same or different;
when Z is a silicon atom, R 9 and R 10 are bonded to the silicon atom, R 9 and R 10 each independently represent R x as defined in formula (1), and R 9 and R 10 are optionally bonded to the structure according to formula (1);
when Z is a silicon atom, R 9 and R 10 are not bonded to each other to form a cyclic structure;
L is a single bond or a linking group;
the linking group is a substituted or unsubstituted, linear, branched or cyclic polyvalent aliphatic hydrocarbon group having 1 to 30 carbon atoms, a substituted or unsubstituted polyvalent aryl group having 6 to 40 ring carbon atoms, or a substituted or unsubstituted polyvalent heteroaryl group having 5 to 40 ring atoms;
the polyvalent heteroaryl group having 5 to 40 ring atoms for L comprises a substituted or unsubstituted polyvalent group derived from a phenanthroline ring according to formula (1);
when c is 2 to 8, plural L are the same or different;
one of Y 1 to Y 8 is a carbon atom bonded to L and a remainder of Y 1 to Y 8 are each independently CR Y ;
at least one R Y is not a hydrogen atom;
each R Y is independently selected from the group consisting of:
a hydrogen atom,
a halogen atom,
a cyano group,
a nitro group,
a substituted or unsubstituted hydroxyl group,
a substituted or unsubstituted carboxyl group,
a substituted or unsubstituted sulfonyl group,
a substituted or unsubstituted boryl group,
a substituted or unsubstituted phosphino group,
a substituted or unsubstituted mercapto group,
a substituted or unsubstituted acyl group,
a substituted or unsubstituted amino group,
a substituted or unsubstituted silyl group,
a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,
a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms,
a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, and
a substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms;
the substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms for R Y is a group selected from a phenyl group, naphthyl group, anthryl group, phenanthryl group, biphenyl group, terphenyl group, quaterphenyl group, fluoranthenyl group, triphenylenyl group, phenanthrenyl group, fluorenyl group, 9,9-dimethylfluorenyl group, spirofluorenyl group, benzo[c]phenanthrenyl group, benzo[a]triphenylenyl group, naphtho[1,2-c]phenanthrenyl group, naphtho[1,2-a]triphenylenyl group, dibenzo[a,c]triphenylenyl group, and benzo[b]fluoranthenyl group;
the heteroaryl group having 5 to 40 ring atoms for R Y comprises a substituted or unsubstituted phenanthrolyl group derived from the phenanthroline ring of formula (1);
adjacent R Y are bonded to each other to form a cyclic structure, or are not bonded to each other;
when X 1 or X 8 is a carbon atom bonded to the group according to formula (2), b is 1, Z is an oxygen atom, Y 4 or Y 5 is a carbon atom bonded to L, and c is 2, the L closer to the phenanthroline ring of formula (1) among two Ls is a divalent group other than an anthracene group;
when X 1 or X 8 is a carbon atom bonded to the group according to formula (2), b and c are 1, Z is an oxygen atom or a sulfur atom, Y 3 is a carbon atom bonded to L, and L is a p-phenylene group, R Y for Y 4 is a group other than a phenyl group;
when X 1 or X 8 is a carbon atom bonded to the group according to formula (2), b and c are 1, Z is an oxygen atom or a sulfur atom, Y 6 is a carbon atom bonded to L, and L is a p-phenylene group, R Y for Y 5 is a group other than a phenyl group;
when X 1 is a carbon atom bonded to the group according to formula (2), Z is a silicon atom, Y 3 is a carbon atom bonded to L, L is a single bond, R Y for Y 6 is bonded to the phenanthrolyl group as a heteroaryl group having 5 to 40 ring atoms with a single bond, the phenanthrolyl group is bonded to R Y for Y 6 at a position other than position 2;
when X 4 or X 5 is a carbon atom bonded to the group according to formula (2), Y 2 is a carbon atom bonded to L, L is a single bond, and Z is an oxygen atom, R Y for Y 7 is a group other than a pyrenyl group; and
when X 4 or X 5 is a carbon atom bonded to the group according to formula (2), Y 7 is a carbon atom bonded to L, L is a single bond, and Z is an oxygen atom, R Y for Y 2 is a group other than a pyrenyl group.
2. The organic electroluminescence device according to claim 1 , wherein L in formula (2) is selected from a single bond or a linking group, the linking group being a phenyl group, a biphenyl group, or a naphthyl group.
3. The organic electroluminescence device according to claim 1 , wherein X 1 or X 8 in formula (1) is a carbon atom bonded to the group according to formula (2).
4. The organic electroluminescence device according to claim 1 , wherein Z in formula (2) is an oxygen atom or a sulfur atom.
5. The organic electroluminescence device according to claim 1 , wherein adjacent R Y in formula (2) are not bonded to each other.
6. The organic electroluminescence device according to claim 1 , wherein:
X 1 or X 8 in formula (1) is a carbon atom bonded to the group according to formula (2); and
L in formula (2) is selected from a single bond or a linking group, the linking group being a phenyl group, a biphenyl group, or a naphthyl group.
7. The organic electroluminescence device according to claim 1 , wherein:
L in formula (2) is selected from a single bond or a linking group, the linking group being a phenyl group, a biphenyl group, or a naphthyl group; and
Z in formula (2) is an oxygen atom or a sulfur atom.
8. The organic electroluminescence device according to claim 1 , wherein:
L in formula (2) is selected from a single bond or a linking group, the linking group being a phenyl group, a biphenyl group, or a naphthyl group; and
adjacent R Y in formula (2) are not bonded to each other.
9. The organic electroluminescence device according to claim 1 , wherein:
X 1 or X 8 in formula (1) is a carbon atom bonded to the group according to formula (2); and
Z in formula (2) is an oxygen atom or a sulfur atom.
10. The organic electroluminescence device according to claim 1 , wherein:
X 1 or X 8 in formula (1) is a carbon atom bonded to the group according to formula (2); and
adjacent R Y in formula (2) are not bonded to each other.
11. The organic electroluminescence device according to claim 1 , wherein:
Z in formula (2) is an oxygen atom or a sulfur atom; and
adjacent R Y in formula (2) are not bonded to each other.
12. The organic electroluminescence device according to claim 1 , wherein:
X 1 or X 8 in formula (1) is a carbon atom bonded to the group according to formula (2);
L in formula (2) is selected from a single bond or a linking group, the linking group being a phenyl group, a biphenyl group, or a naphthyl group; and
Z in formula (2) is an oxygen atom or a sulfur atom.
13. The organic electroluminescence device according to claim 1 , wherein:
X 1 or X 8 in formula (1) is a carbon atom bonded to the group according to formula (2);
L in formula (2) is selected from a single bond or a linking group, the linking group being a phenyl group, a biphenyl group, or a naphthyl group; and
adjacent R Y in formula (2) are not bonded to each other.
14. The organic electroluminescence device according to claim 1 , wherein:
L in formula (2) is selected from a single bond or a linking group, the linking group being a phenyl group, a biphenyl group, or a naphthyl group;
Z in formula (2) is an oxygen atom or a sulfur atom; and
adjacent R Y in formula (2) are not bonded to each other.
15. The organic electroluminescence device according to claim 1 , wherein:
X 1 or X 8 in formula (1) is a carbon atom bonded to the group according to formula (2);
Z in formula (2) is an oxygen atom or a sulfur atom; and
adjacent R Y in formula (2) are not bonded to each other.
16. The organic electroluminescence device according to claim 1 , wherein:
X 1 or X 8 in formula (1) is a carbon atom bonded to the group according to formula (2);
L in formula (2) is selected from a single bond or a linking group, the linking group being a phenyl group, a biphenyl group, or a naphthyl group;
Z in formula (2) is an oxygen atom or a sulfur atom; and
adjacent R Y in formula (2) are not bonded to each other.
17. The organic electroluminescence device according to claim 1 , wherein Z in formula (2) is an oxygen atom.
18. The organic electroluminescence device according to claim 1 , wherein L in formula (2) is a single bond.
19. The organic electroluminescence device according to claim 1 , wherein L in formula (2) is a linking group, the linking group being a phenyl group, a biphenyl group, or a naphthyl group.
20. The organic electroluminescence device according to claim 1 , wherein:
one of X 1 to X 8 in formula (1) is a carbon atom bonded to the group according to formula (2); and
the rest of X 1 to X 8 are CR x .