Polymeric compound, electroluminescent device material, electroluminescent device, and electronic device
As a technology capable of improving the durability of an electroluminescent device, for example, luminescence lifespan, a polymeric compound including a structural unit represented by Chemical Formula 1, or a structural unit represented by Chemical Formula 1 and a structural unit represented by Chemical Formula 2, and an electroluminescent device material or electroluminescent device including the same are provided: In Chemical Formula 1 and Chemical Formula 2, R 11 to R 14 are not the same as R 41 to R 44 .
1 . A polymeric compound comprising a structural unit represented by Chemical Formula 1:
wherein, in Chemical Formula 1,
R 11 to R 14 , R 21 , R 22 , R 31 , and R 32 are each independently a hydrogen atom or a hydrocarbon group having 1 to 18 carbon atoms,
L 1 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring-forming atoms, or a substituted or unsubstituted heteroaromatic ring group having 5 to 14 ring-forming atoms,
x is 0, 1, or 2, and when x is 2, each occurrence of L 1 is the same as or different from each other,
L 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring-forming atoms, or a substituted or unsubstituted heteroaromatic ring group having 5 to 14 ring-forming atoms, wherein L 2 optionally forms a ring with Ar 1 ,
Ar 1 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring-forming atoms, or a substituted or unsubstituted heteroaromatic ring group having 5 to 14 ring-forming atoms, wherein Ar 1 optionally forms a ring with Ar 2 or L 2 , and
Ar 2 is (i) an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted with a linear hydrocarbon group having 1 to 12 carbon atoms, a branched hydrocarbon group having 3 to 12 carbon atoms, an aromatic hydrocarbon group having 6 to 25 ring-forming atoms, or a divalent heteroaromatic ring group having 5 to 14 ring-forming atoms, or (ii) an heteroaromatic ring group having 5 to 14 ring-forming atoms substituted with a linear hydrocarbon group having 1 to 12 carbon atoms, a branched hydrocarbon group having 3 to 12 carbon atoms, an aromatic hydrocarbon group having 6 to 25 ring-forming atoms, or a divalent heteroaromatic ring group having 5 to 14 ring-forming atoms, wherein Ar 2 optionally forms a ring with Ar 1 .
2 . The polymeric compound of claim 1 , wherein the polymeric compound further comprises a structural unit represented by Chemical Formula 2:
wherein, in Chemical Formula 2,
R 41 to R 44 , R 23 , R 24 , R 33 , and R 34 are each independently a hydrogen atom, or a hydrocarbon group having 1 to 18 carbon atoms, wherein R 41 to R 44 are different from R 11 to R 14 of Chemical Formula 1,
L 3 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring-forming atoms, or a substituted or unsubstituted heteroaromatic ring group having 5 to 14 ring-forming atoms,
y is 0, 1, or 2, and when y is 2, each occurrence of L 3 is the same as or different from each other,
L 4 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring-forming atoms or a substituted or unsubstituted heteroaromatic ring group having 5 to 14 ring-forming atoms, wherein L 4 optionally forms a ring with Ar 3 ,
Ar 3 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring-forming atoms, or a substituted or unsubstituted heteroaromatic ring group having 5 to 14 ring-forming atoms, wherein Ar 3 optionally forms a ring with Ar 4 or L 4 , and
Ar 4 is (i) an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted with a linear hydrocarbon group having 1 to 12 carbon atoms, a branched hydrocarbon group having 3 to 12 carbon atoms, an aromatic hydrocarbon group having 6 to 25 ring-forming atoms, or a divalent heteroaromatic ring group having 5 to 14 ring-forming atoms, or (ii) an heteroaromatic ring group having 5 to 14 ring-forming atoms substituted with a linear hydrocarbon group having 1 to 12 carbon atoms, a branched hydrocarbon group having 3 to 12 carbon atoms, an aromatic hydrocarbon group having 6 to 25 ring-forming atoms, or a divalent heteroaromatic ring group having 5 to 14 ring-forming atoms, wherein Ar 4 optionally forms a ring with Ar 3 .
3 . The polymeric compound of claim 2 , wherein R 11 to R 14 of Chemical Formula 1 are each independently a hydrocarbon group having 3 to 9 carbon atoms, and R 41 to R 44 in Chemical Formula 2 are each independently a hydrocarbon group having 10 to 14 carbon atoms.
4 . The polymeric compound of claim 2 , wherein R 21 , R 22 , R 31 , R 32 , L 1 , x, L 2 , Ar 1 , and Ar 2 of Chemical Formula 1 are the same as R 23 , R 24 , R 33 , R 34 , L 3 , y, L 4 , Ar 3 , and Ar 4 of Chemical Formula 2, respectively.
5 . The polymeric compound of claim 2 , wherein a mole ratio of the structural unit represented by Chemical Formula 2 to the structural unit represented by Chemical Formula 1 is greater than or equal to about 1 mole and less than or equal to about 20 moles based on 1 mole of the structural unit represented by Chemical Formula 1.
6 . The polymeric compound of claim 1 , wherein the following structure in Chemical Formula 1:
comprises a structure selected from Group 1:
wherein, in Group 1, R 51 to R 54 are each independently a hydrogen atom, a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 3 to 12 carbon atoms, or a group selected from the following groups:
wherein, in Group 1, Ar 41 to Ar 417 are each independently a group selected from the following groups:
wherein, in the chemical formulas, R 55 to R 57 are each independently a hydrogen atom, a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 3 to 12 carbon atoms, or a group selected from the following groups:
wherein, in the chemical formulas, R 58 and R 59 are each independently a hydrogen atom, a linear alkyl group having 1 to 12 carbon atoms, or a branched alkyl group having 3 to 12 carbon atoms.
7 . The polymeric compound of claim 2 , wherein the following structure in Chemical Formula 2:
comprises a structure selected from Group 1:
wherein, in Group 1, R 51 to R 54 are each independently a hydrogen atom, a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 3 to 12 carbon atoms, or a group selected from the following groups:
Ar 4 ˜ to Ar 417 of Group 1 are each independently a group selected from the following group:
wherein, in the chemical formulas, R 55 to R 57 are each independently a hydrogen atom, a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 3 to 12 carbon atoms, or a group selected from the following groups:
wherein, in the chemical formulas, R 58 and R 59 are each independently a hydrogen atom, a linear alkyl group having 1 to 12 carbon atoms, or a branched alkyl group having 3 to 12 carbon atoms.
8 . The polymeric compound of claim 2 , wherein the following structure in Chemical Formula 1:
or the following structure in Chemical Formula 2:
comprises a structure of Group 2:
wherein, in Group 2, Ar 412 to Ar 416 are each independently a group selected from the following groups:
wherein, in the chemical formulas, R 55 to R 57 are each independently a linear alkyl group having 4 to 10 carbon atoms, or a branched alkyl group having 4 to 10 carbon atoms.
9 . The polymeric compound of claim 1 , wherein the structural unit represented by Chemical Formula 1 is represented by one or more of the following structural units:
wherein, in the structural units,
R 11 to R 14 , R 21 , and R 22 are defined as in Chemical Formula 1, and
Ar 411 to Ar 417 are each independently a group selected from the following groups:
wherein, in the chemical formulas, R 55 to R 57 are each independently a hydrogen atom, a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 3 to 12 carbon atoms, or a group selected from the following groups:
wherein, in the chemical formulas, R 58 and R 59 are each independently a hydrogen atom, a linear alkyl group having 1 to 12 carbon atoms, or a branched alkyl group having 3 to 12 carbon atoms.
10 . The polymeric compound of claim 2 , wherein the structural unit represented by Chemical Formula 2 is represented by one or more of the following structural units:
wherein, in the structural units,
R 41 to R 44 , R 23 , and R 24 are defined as in Chemical Formula 2, and
Ar 412 to Ar 416 are each independently a group selected from the following groups:
wherein, in the chemical formulas, R 55 to R 57 are each independently a linear alkyl group having 4 to 10 carbon atoms, or a branched alkyl group having 4 to 10 carbon atoms.
11 . An electroluminescent device material comprising the polymeric compound of claim 1 .
12 . The electroluminescent device material of claim 11 , wherein the polymeric compound further comprises a structural unit represented by Chemical Formula 2:
wherein, in Chemical Formula 2,
R 41 to R 44 , R 23 , R 24 , R 33 , and R 34 are each independently a hydrogen atom, or a hydrocarbon group having 1 to 18 carbon atoms, wherein R 41 to R 44 are different from R 11 to R 14 of Chemical Formula 1,
L 3 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring-forming atoms, or a substituted or unsubstituted heteroaromatic ring group having 5 to 14 ring-forming atoms,
y is 0, 1, or 2, and when y is 2, each occurrence of L 3 is the same as or different from each other,
L 4 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring-forming atoms, or a substituted or unsubstituted heteroaromatic ring group having 5 to 14 ring-forming atoms, wherein L 4 optionally forms a ring with Ar 3 ,
Ar 3 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring-forming atoms, or a substituted or unsubstituted heteroaromatic ring group having 5 to 14 ring-forming atoms, wherein Ar 3 optionally forms a ring with Ar 4 or L 4 , and
Ar 4 is (i) an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted with a linear hydrocarbon group having 1 to 12 carbon atoms, a branched hydrocarbon group having 3 to 12 carbon atoms, an aromatic hydrocarbon group having 6 to 25 ring-forming atoms, or a heteroaromatic ring group having 5 to 14 ring-forming atoms, or (ii) an heteroaromatic ring group having 5 to 14 ring-forming atoms substituted with a linear hydrocarbon group having 1 to 12 carbon atoms, a branched hydrocarbon group having 3 to 12 carbon atoms, an aromatic hydrocarbon group having 6 to 25 ring-forming atoms, or a heteroaromatic ring group having 5 to 14 ring-forming atoms, wherein Ar 4 optionally forms a ring with Ar 3 .
13 . An electroluminescent device, comprising
a first electrode, a second electrode, and at least one organic film disposed between the first electrode and the second electrode,
wherein the at least one organic film comprises the polymeric compound of claim 1 .
14 . The electroluminescent device of claim 13 , wherein the at least one organic film comprising the polymeric compound is a hole transport layer or a hole injection layer.
15 . The electroluminescent device of claim 13 , wherein the at least one organic film further comprises a light emitting layer comprising semiconductor nanoparticles or organometallic complexes.
16 . An electroluminescent device, comprising
a first electrode, a second electrode, and at least one organic film disposed between the first electrode and the second electrode,
wherein the at least one organic film comprises the polymeric compound of claim 2 .
17 . The electroluminescent device of claim 16 , wherein the at least one organic film comprising the polymeric compound is a hole transport layer or a hole injection layer.
18 . The electroluminescent device of claim 16 , wherein the at least one organic film further comprises a light emitting layer comprising a semiconductor nanoparticle or an organometallic complex.
19 . An electronic device comprising the electroluminescent device of claim 13 .