Polymer, a composition, and an electroluminescent device
As a means for providing an electroluminescent device capable of achieving high luminance, high efficiency, and at the same time excellent device life-span, a polymer having an overlap index of greater than or equal to about 0.00001 and less than or equal to about 1.8, and a polymer including a structural unit represented by Chemical Formula (1) are provided:
1 . A polymer comprising a structural unit represented by Chemical Formula (1):
wherein, in Chemical Formula (1),
Ar 1 and Ar 2 are each independently a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 60 carbon atoms,
Ar 3 is selected from Group (I):
wherein, in Group (I),
R 111 to R 123 are each independently a hydrogen atom or a linear or branched hydrocarbon group having 1 to 16 carbon atoms, and
* indicates a bonding position with an adjacent atom,
Ar 4 is a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 60 carbon atoms or a substituted or unsubstituted divalent aromatic heterocyclic ring group having 3 to 60 ring atoms,
Ar 5 is a single bond or a substituted or unsubstituted divalent aromatic heterocyclic ring group having 3 to 60 ring atoms,
each R 1 is independently a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkylthiol group, an alkoxy group, an alkoxyalkyl group, an alkylthioalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, an alkylthiocarbonyl group, a hydroxyl group, a carboxyl group, a thiocarboxyl group, a dithiocarboxyl group, a thiol group, or a cyano group,
each R 2 is independently a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkylthiol group, an alkoxy group, an alkoxyalkyl group, an alkylthioalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, an alkylthiocarbonyl group, a hydroxyl group, a carboxyl group, a thiocarboxyl group, a dithiocarboxyl group, a thiol group, a cyano group, and
A is a structure represented by Chemical Formula (2) or Chemical Formula (3):
wherein, in Chemical Formula (2),
each Ar 6 is independently a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, an alkylthiol group, an alkylthiocarbonyl group, a thiocarboxyl group, a dithiocarboxyl group, an alkylthioalkyl group, a hydroxyl group, a carboxyl group, a thiol group, a cyano group, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic ring group having 3 to 60 ring atoms, or a substituted or unsubstituted monovalent ring set group including a structure in which one or more aromatic hydrocarbon rings having 6 to 60 carbon atoms and one or more aromatic heterocyclic rings having 3 to 60 ring atoms are bonded through a single bond,
each Ar 7 is independently a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, an alkylthiol group, an alkylthiocarbonyl group, a thiocarboxyl group, a dithiocarboxyl group, an alkylthioalkyl group, a hydroxyl group, a carboxyl group, a thiol group, a cyano group, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic ring group having 3 to 60 ring atoms, or a substituted or unsubstituted monovalent ring set group including a structure in which one or more aromatic hydrocarbon rings having 6 to 60 carbon atoms and one or more aromatic heterocyclic rings having 3 to 60 ring atoms are bonded through a single bond,
two or more Ar 7 s optionally form a condensed ring with the benzene ring to which two or more Ar 7 are bonded, and
* indicates a bonding position with an adjacent atom;
wherein, in Chemical Formula (3),
each Ar 8 is independently a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, an alkylthiol group, an alkylthiocarbonyl group, a thiocarboxyl group, a dithiocarboxyl group, an alkylthioalkyl group, a hydroxyl group, a carboxyl group, a thiol group, a cyano group, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic ring group having 3 to 60 ring atoms, or a substituted or unsubstituted monovalent ring set group including a structure in which one or more aromatic hydrocarbon rings having 6 to 60 carbon atoms and one or more aromatic heterocyclic rings having 3 to 60 ring atoms are bonded through a single bond,
each Ar 9 is independently a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, an alkylthiol group, an alkylthiocarbonyl group, a thiocarboxyl group, a dithiocarboxyl group, an alkylthioalkyl group, a hydroxyl group, a carboxyl group, a thiol group, a cyano group, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic ring group having 3 to 60 ring atoms, or a substituted or unsubstituted monovalent ring set group including a structure in which one or more aromatic hydrocarbon rings having 6 to 60 carbon atoms and one or more aromatic heterocyclic rings having 3 to 60 ring atoms are bonded through a single bond,
X is S, O, or C substituted with two substituted or unsubstituted linear or branched hydrocarbon groups having 1 to 16 carbon atoms,
two or more Ar 9 s optionally form a condensed ring with the benzene ring to which two or more Ar 9 s are bonded, and
* indicates a bonding position with an adjacent atom.
2 . The polymer of claim 1 , wherein at least one of Ar 1 , Ar 2 , and Ar 4 in Chemical Formula (1) is each independently a group selected from Group (II):
wherein R 211 to R 225 are each independently a hydrogen atom, or linear or branched hydrocarbon group having 1 to 16 carbon atoms, and
* indicates a bonding position with an adjacent atom.
3 . The polymer of claim 2 , wherein in Chemical Formula (1), Ar 1 , Ar 2 , and Ar 4 are each independently a group selected from Group (II).
4 . A polymer comprising at least one structural unit selected from Group (A);
wherein, in the chemical formulas of Group (A), n represents an integer,
when the compounds represented by the chemical formulas have two or more groups represented by “C n H 2n+1 —”,
n in each “C n H 2n+1 —” is the same as or different from each other, and
each group represented by “C n H 2n+1 —” is the same as or different from each other.
5 . The polymer of claim 4 , wherein the structural unit is at least one structural unit selected from Group (B):
wherein, in the above chemical formulas, the group represented by “C 12 H 25 -” represents an n-dodecyl group,
the group represented by “C 10 H 21 —” represents an n-decyl group,
the group represented by “C 8 H 17 —” represents an n-octyl group, and
the group represented by “C 6 H 13 —” represents an n-hexyl group.
6 . The polymer of claim 4 , wherein the structural unit is at least one structural unit selected from Group (B′):
wherein, in the above chemical formulas, the group represented by “C 8 H 17 —” represents an n-octyl group.
7 . A composition comprising the polymer of claim 1 .
8 . The composition of claim 7 , wherein the composition further comprises a low molecular weight material satisfying the following condition (a) and at the same time satisfying the following condition (b), the following condition (c), or a combination thereof:
(a) a band gap of the low molecular weight material is larger than the polymer,
(b) a LUMO of the low molecular weight material is shallower than the LUMO of the polymer, and
(c) a HOMO of the low molecular weight material is deeper than the HOMO of the polymer.
9 . An electroluminescent device comprising
a pair of electrodes, and at least one organic film comprising the polymer of claim 1 .
10 . An electroluminescent device comprising a pair of electrodes, and one or two or more organic layers comprising, wherein at least one the organic layer comprises the polymer of claim 1 , and a low molecular weight material satisfying the following condition (a) and satisfying the following condition (b), the following condition (c), or a combination thereof:
(a) a band gap of the low molecular weight material is larger than the polymer,
(b) a LUMO of the low molecular weight material is shallower than the polymer, and
(c) a HOMO of the low molecular weight material is deeper than the polymer.
11 . An electroluminescent device comprising
a pair of electrodes, and at least one organic film comprising the composition of claim 7 .
12 . The electroluminescent device of claim 9 , wherein the electroluminescent device further comprises a layer comprising quantum dots.
13 . The electroluminescent device of claim 10 , wherein the electroluminescent device further comprises a layer comprising quantum dots.
14 . The electroluminescent device of claim 11 , wherein the electroluminescent device further comprises a layer comprising quantum dots.
15 . The polymer of claim 1 , wherein the polymer has an overlap index of greater than or equal to about 0.00001 and less than or equal to about 1.8 represented by the following equation:
overlap
index
=
(
∑
k
=
1
n
(
d
HOMO
k
×
d
LUMO
k
)
)
×
100
wherein, in the equation, k is a serial number assigned to an atom in the chemical formula of a structural unit constituting the polymer, d k HOMO denotes a distribution density of the HOMO in the atom of serial number k, and d k LUMO denotes a distribution density of the LUMO in the atom of serial number k.
16 . The polymer of claim 15 , wherein the overlap index of greater than or equal to about 0.00001 and less than or equal to about 1.2.