Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device
A compound may improve the capability of an organic EL device, and an organic electroluminescent device including such compound may have improved capability and may be included in electronic devices. Such compounds may be of formula (1A) or formula (1B) (wherein the symbols are as defined in the description) organic electroluminescent device(s) may contain such compound(s), and electronic device(s) may include such organic electroluminescent device(s).
1 . A compound represented by the following formula (1A):
in the formula (1A),
N* is a central nitrogen atom,
p represents 0 or 1,
q represents 0 or 1,
provided that p+q≥1,
when p is 0 and q is 1, *a bonds to the nitrogen atom N*, and one selected from R 6 to R 10 is a single bond bonding to *b,
when p is 1 and q is 0, one selected from R 1 to R 5 is a single bond bonding to *b,
when p is 1 and q is 1, one selected from R 1 to R 5 is a single bond bonding to *a, and one selected from R 6 to R 10 is a single bond bonding to *b,
R 1 to R 5 that are not a single bond bonding to *a or *b, R 6 to R 10 that are not a single bond bonding to *b, R 11 to R 14 , and R 21 to R 27 each independently represent
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 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 aryloxy 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 having substituent(s) 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, and a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,
adjacent two selected from R 1 to R 5 that are not a single bond, adjacent two selected from R 6 to R 10 that are not a single bond, adjacent two selected from R 11 to R 14 that are not a single bond, and adjacent two selected from R 21 to R 27 do not bond to each other and therefore do not form a cyclic structure,
provided that one or more pairs of two benzene rings bonding to each other selected from the benzene ring U, the benzene ring V and the benzene ring W may be crosslinked with CR x R y to form a substituted or unsubstituted fluorene structure, or may not be crosslinked and may not form a fluorene structure,
R x and R y each independently represent a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and R x and R y may bond via a single bond,
Ar 1 and Ar 2 each are independently represented by any of the following formulae (1-a) to (1-e):
in the formula (1-a),
R 31 to R 35 , R 41 to R 46 , and R 51 to R 55 each independently represent
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 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 aryloxy 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 having substituent(s) 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, and a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,
provided that,
one selected from R 31 to R 35 is a single bond bonding to *c,
one selected from R 41 to R 46 is a single bond bonding to *d, and the other one selected from R 41 to R 46 is a single bond bonding to *e,
** is a bonding position to the nitrogen atom N*,
m1 represents 0 or 1, and n1 represents 0 or 1,
when m1 is 0 and n1 is 0, *e bonds to the nitrogen atom N*
when m1 is 0 and n1 is 1, *c bonds to the nitrogen atom N*,
when m1 is 1 and n1 is 0, one selected from R 31 to R 35 is a single bond bonding to *e,
k represents 1 or 2,
adjacent two selected from R 31 to R 35 that are not a single bond, adjacent two selected from R 41 to R 46 that are not a single bond, and adjacent two selected from R 51 to R 55 do not bond to each other and therefore do not form a cyclic structure,
the benzene ring A and the benzene ring B, the benzene ring A and the benzene ring C, and the benzene ring B and the benzene ring C do not crosslink;
in the formula (1-b),
R 61 to R 68 each independently represent
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 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 aryloxy 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 having substituent(s) 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, and a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,
provided that, one selected from R 61 to R 68 is a single bond bonding to *f,
** represents a bonding position to the nitrogen atom N*,
adjacent two selected from R 61 to R 68 that are not a single bond do not bond to each other and therefore do not form a cyclic structure;
in the formula (1-c),
R 31 to R 35 , R 41 to R 46 , **, *c, *d, and *e are the same as above,
R 71 to R 80 each independently represent
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 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 aryloxy 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 having substituent(s) 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, and a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,
provided that, one selected from R 71 to R 80 is a single bond bonding to *h,
m2 represents 0 or 1, n2 represents 0 or 1,
when m2 is 0 and n2 is 0, *e bonds to the nitrogen atom N*,
when m2 is 0 and n2 is 1, *c bonds to the nitrogen atom N*,
when m2 is 1 and n2 is 0, one selected from R 31 to R 35 is a single bond bonding to *e,
adjacent two selected from R 31 to R 35 that are not a single bond, adjacent two selected from R 41 to R 46 that are not a single bond, and adjacent two selected from R 71 to R 80 do not bond to each other and therefore do not form a cyclic structure,
the benzene ring A and the benzene ring B do not crosslink;
in the formula (1-d),
R 31 to R 35 , R 41 to R 46 , **, *c, *d, and *e are the same as above,
R 81 to R 92 each independently represent
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 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 aryloxy 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 having substituent(s) 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, and a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,
provided that, one selected from R 81 to R 92 is a single bond bonding to *g,
m3 represents 0 or 1, n3 represents 0 or 1,
when m3 is 0 and n3 is 0, *e bonds to the nitrogen atom N*,
when m3 is 0 and n3 is 1, *c bonds to the nitrogen atom N*,
when m3 is 1 and n3 is 0, one selected from R 31 to R 35 is a single bond bonding to *e,
adjacent two selected from R 31 to R 35 that are not a single bond, adjacent two selected from R 41 to R 46 that are not a single bond, and adjacent two selected from R 81 to R 92 do not bond to each other and therefore do not form a cyclic structure,
the benzene ring A and the benzene ring B do not crosslink;
in the formula (1-e),
R 31 to R 35 , **, and *c are the same as above,
R 101 to R 108 each independently represent
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 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 aryloxy 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 having substituent(s) 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, and a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,
provided that, one selected from R 101 to R 108 is a single bond bonding to *i,
m4 represents 0 or 1,
one of R a and R b is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and the other is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or R a and R b each are independently a substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,
adjacent two selected from R 101 to R 104 and R 105 to R 108 that are not a single bond do not bond to each other and therefore do not form a cyclic structure,
provided that when Ar 1 is represented by the formula (1-e), m4 is 1, and when Ar 2 is represented by the formula (1-e), m4 is 0 or 1,
** represents a bonding position to the nitrogen atom N*,
wherein, when either one of Ar 1 or Ar 2 has formula (1-b), (1-c), or (1-d), the other of Ar 1 and Ar 2 has formula (1-a), and
wherein, when Ar 1 or Ar 2 has formula (1-e), m4 is 1.
2 . The compound of claim 1 , represented by any of the following formulae (1A-1), (1A-2), and (1A-5) to (1A-7):
wherein N*, *b, *c, *d, *e, *f, *i, k, n1, m1, m4, R a , R b , R 1 to R 5 , R 11 to R 14 , R 21 to R 27 , R 31 to R 35 , R 41 to R 46 , R 51 to R 55 , R 61 to R 68 , R 71 to R 80 , and R 101 to R 108 are as defined in the formula (1A).
3 . The compound of claim 1 , represented by any of the following formulae (1A-2-1) to (1A-2-4),
wherein N*, *b, *c, *d, *e, k, n1, m1, m4, R 1 to R 5 , R 11 to R 14 , R 21 to R 27 , R 31 to R 35 , R 41 to R 46 , R 51 to R 55 , and R 101 to R 108 are as defined in the formula (1A), R 131 to R 140 are the same as R 101 to R 108 defined in the formula (IA).
4 . The compound of claim 1 , wherein the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms represented by R a , R b , R 1 to R 5 , R 6 to R 10 , R 11 to R 14 , R 21 to R 27 , R 31 to R 35 , R 41 to R 46 , R 51 to R 55 , R 61 to R 68 , R 71 to R 80 , R 81 to R 92 , R 101 to R 108 , and R 131 to R 140 is independently selected from a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group and a t-butyl group.
5 . The compound of claim 1 , wherein the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms represented by R a and R b is independently selected from a phenyl group, a biphenyl group, a naphthyl group, and a phenanthryl group.
6 . The compound of claim 1 , wherein the compound represented by the formula (1A) comprises a deuterium atom.
7 . A material for an electroluminescent device, comprising:
the compound of claim 1 .
8 . An organic electroluminescent device, comprising:
an anode;
a cathode; and
organic layers intervening between the anode and the cathode, the organic layers comprising a light emitting layer,
wherein at least one layer of the organic layers comprises the compound of claim 1 .
9 . The device of claim 8 , wherein the compound comprises a deuterium atom.
10 . The device of claim 8 , wherein the organic layer comprises a hole transporting zone between the anode and the light emitting layer, and
wherein the hole transporting zone comprises the compound.
11 . The device of claim 10 , wherein the hole transporting zone comprises a first hole transporting layer on the anode side and a second hole transporting layer on the cathode side, and
wherein the first hole transporting layer and/or the second hole transporting layer comprises the compound.
12 . The device of claim 11 , wherein the second hole transporting layer comprises the compound.
13 . The device of claim 11 , wherein the second hole transporting layer is adjacent to the light emitting layer.
14 . The compound of claim 1 , wherein Ar1 and/or Ar2 has the formula (1-a):
and
in the formula (1-a), *c is bonded to R 31 , R 33 , or R 35 , and *e is bonded to benzene ring B in the ortho or para position.