Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device
The compounds represented by formula (1): wherein each symbol is as defined in the description, provide organic electroluminescence devices having device performance further improved.
1 . A compound represented by formula (1):
wherein:
N* is a central nitrogen atom,
R 1 to R 7 are each independently
a hydrogen atom, a halogen atom, a nitro group, a cyano group,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms,
a substituted or unsubstituted haloalkoxy group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms,
a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms,
a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms,
a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or
a mono-, di- or tri-substituted silyl group wherein the substituent is selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
R a and R b are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or an unsubstituted phenyl group,
wherein adjacent two selected from R 1 to R 7 , R a and R b are not bonded to each other, thereby failing to form a ring structure,
L is a single bond or a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, Ar 1 is represented by formula (1-a) and Ar 2 is represented by formula (1-b) or (1-c):
wherein:
R 11 to R 18 , R 21 to R 25 , and R 31 to R 35 are each independently
a hydrogen atom, a halogen atom, a nitro group, a cyano group,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms,
a substituted or unsubstituted haloalkoxy group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms,
a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms,
a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms,
a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or
a mono-, di- or tri-substituted silyl group wherein the substituent is selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
wherein:
one selected from R 11 to R 18 is a single bond bonded to *a,
one selected from R 21 to R 25 is a single bond bonded to *b,
one selected from R 31 to R 35 is a single bond bonded to *c,
* is a bonding site to the central nitrogen atom N*
m1 is 0 or 1, n1 is 0 or 1,
when m1 is 0 and n1 is 0, *c is bonded to the central nitrogen atom N*,
when m1 is 0 and n1 is 1, *b is bonded to the central nitrogen atom N* and *c is bonded to R 33 ,
when m1 is 1 and n1 is 0, *c is bonded to R 23 ,
when m1 is 1 and n1 is 1, *c is bonded to R 33 ,
R 11 to R 18 not the single bond, R 21 to R 25 not the single bond, and R 31 to R 35 not the single bond are not bonded to each other, thereby failing to form a ring structure,
wherein:
R 41 to R 48 , R 51 to R 55 , and R 61 to R 65 are each independently
a hydrogen atom, a halogen atom, a nitro group, a cyano group,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms,
a substituted or unsubstituted haloalkoxy group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms,
a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms,
a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms,
a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or
a mono-, di- or tri-substituted silyl group wherein the substituent is selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
wherein:
one selected from R 41 to R 48 is a single bond bonded to *d,
one selected from R 51 to R 55 is a single bond bonded to *e,
one selected from R 61 to R 65 is a single bond bonded to *f,
* is a bonding site to the central nitrogen atom N*,
m2 is 0 or 1 and n2 is 0 or 1,
when m2 is 0 and n2 is 0, *f is bonded to the central nitrogen atom N*,
when m2 is 0 and n2 is 1, *e is bonded to the central nitrogen atom N* and *f is bonded to R 63 ,
when m2 is 1 and n2 is 0, *f is bonded to R 53 ,
when m2 is 1 and n2 is 1, *f is bonded to R 63 ,
R 41 to R 48 not the single bond, R 51 to R 55 not the single bond and R 61 to Re not the single bond are not bonded to each other, thereby failing to form a ring structure,
wherein:
R 71 to R 75 , R 81 to R 86 , and R 91 to R 95 are each independently
a hydrogen atom, a halogen atom, a nitro group, a cyano group,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms,
a substituted or unsubstituted haloalkoxy group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms,
a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms,
a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms,
a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or
a mono-, di- or tri-substituted silyl group wherein the substituent is selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
wherein;
one selected from R 71 to R 75 is a single bond bonded to *g,
one selected from R 81 to R 86 is a single bond bonded to *h and another one selected from R 81 to R 86 is a single bond bonded to *i,
* is a bonding site to the central nitrogen atom N*,
R 71 to R 75 not the single bond, R 51 to R 86 not the single bond, and R 91 to R 95 are not bonded to each other, thereby failing to form a ring structure.
2 . The compound according to claim 1 , which is represented by formula (2) or (3):
wherein N*, L, *a, *b, *c, *d, *e, *f, *g, *h, *i, m1, m2, n1, n2, R 1 to R 7 , R 11 to R 18 , R 21 to R 25 , R 31 to R 35 , R 41 to R 48 , R 31 to R 55 , R 61 to R 65 , R 71 to R 75 , R 81 to R 56 , R 91 to R 95 , R a , and R b are each independently as defined in formula (1).
3 . The compound according to claim 1 , which is represented by any of formulae (2-1), (2-2), (2-3), (3-1), (3-2), and (3-3):
wherein:
N*, *a, *b, *c, *d, *e, *f, *g, *h, *i, m1, m2, n1, n2, R 1 to R 7 , R 11 to R 18 , R 21 to R 25 , R 31 to R 35 , R 41 to R 48 , R 51 to R 55 , R 61 to R 65 , R 71 to R 75 , R 81 to R 86 , R 91 to R 95 , R a , and R b are each independently as defined in formula (1),
R 101 to R 105 and R 111 to R 118 are each independently
a hydrogen atom, a halogen atom, a nitro group, a cyano group,
a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,
a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms,
a substituted or unsubstituted haloalkoxy group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms,
a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms,
a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms,
a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or
a mono-, di- or tri-substituted silyl group wherein the substituent is selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
wherein:
one selected from R 101 to R 105 is a single bond boded to *j,
R 101 to R 105 not the single bond are not bonded to each other and are each independently not bonded to R 1 to R 7 , R a , and R b , thereby failing to form a ring structure,
one selected from R 111 to R 118 a single bond boded to *k and another one selected from R 111 to R 118 a single bond boded to *p, and
R 111 to R 118 not the single bond are not bonded to each other and are each independently not bonded to R 1 to R 7 , R a , and R b , thereby failing to form a ring structure.
4 . The compound according to claim 3 , wherein the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms for R 101 to R 105 and R 111 to R 118 are each independently selected from the group consisting of a phenyl group, a biphenyl group a naphthyl group, and a phenanthryl group.
5 . The compound according to claim 3 , wherein R 111 to R 118 not the single bond bonded to *k and not the single bond bonded to *p are all hydrogen atoms.
6 . The compound according to claim 1 , wherein the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms for R 1 to R 7 , R 11 to R 18 , R 21 to R 25 , R 31 to R 35 , R 41 to R 48 , R 51 to R 53 , R 61 to R 65 , R 71 to R 75 , R 81 to R 86 , R 91 to R 95 , R a , and R b are each independently selected from the group consisting of a methyl group, an ethyl group, a n-propyl group, an isopropyl group a n-butyl group, an isobutyl group, a s-butyl group, and a t-butyl group.
7 . The compound according to claim 1 , wherein R a and R b are both unsubstituted phenyl groups or methyl groups, or one of R a and R b is a methyl group and the other is an unsubstituted phenyl group.
8 . The compound according to claim 1 , wherein R 1 to R 7 are all hydrogen atoms.
9 . The compound according to claim 1 , wherein R 1 to R 18 not the single bond bonded to *a are all hydrogen atoms.
10 . The compound according to claim 1 , wherein R 21 to R 25 not the single bond bonded to *b are all hydrogen atoms.
11 . The compound according to claim 1 , wherein R 31 to R 35 not the single bond bonded to *c are all hydrogen atoms.
12 . The compound according to claim 1 , wherein R 41 to R 48 not the single bond bonded to *d are all hydrogen atoms.
13 . The compound according to claim 1 , wherein R 51 to R 55 not the single bond bonded to *e are all hydrogen atoms.
14 . The compound according to claim 1 , wherein Rel to R 65 not the single bond bonded to *f are all hydrogen atoms.
15 . The compound according to claim 1 , wherein R 71 to R 75 not the single bond bonded to *g are all hydrogen atoms.
16 . The compound according to claim 1 , wherein the compound represented by formula (1) comprises at least one heavy hydrogen atom.
17 . An organic electroluminescence device comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein
the organic layer comprises a light emitting layer, and
at least one layer of the organic layer comprises the compound according to claim 1 .
18 . The organic electroluminescence device according to claim 17 , wherein the organic layer comprises a hole transporting region between the anode and the light emitting layer, and
wherein the hole transporting region comprises the compound.
19 . The organic electroluminescence device according to claim 18 , wherein the hole transporting region comprises a first hole transporting layer at an anode side and a second hole transporting layer at a cathode side, and
wherein the first hole transporting layer, the second hole transporting layer, or both comprise the compound.
20 . The organic electroluminescence device according to claim 19 , wherein the second hole transporting layer comprises the compound.