Composition for organic optoelectronic element, organic optoelectronic element, and display device
The present invention relates to: a composition for an organic optoelectronic element, containing at least one first compound represented by chemical formula 1, at least one second compound among compounds represented by chemical formula 2 and compounds composed of combinations of moieties represented by chemical formula 3 and moieties represented by chemical formula 4, and at least one third compound represented by chemical formula 5; an organic optoelectronic element comprising the same; and a display device comprising the organic optoelectronic element. Chemical formulas 1 to 5 are as described in the specification.
1. A composition for an organic optoelectronic device, the composition comprising a mixture of:
at least one first compound represented by Chemical Formula 1,
at least one second compound selected from a compound represented by Chemical Formula 2, and a compound consisting of a combination of a moiety represented by Chemical Formula 3 and a moiety represented by Chemical Formula 4, and
at least one third compound,
wherein, in Chemical Formula 1,
Z is independently N, C, or CR a ,
at least one of Z is N,
R 1 to R 6 and R a are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof,
R 1 to R 6 and R a are independently present or adjacent groups are linked to each other to form a ring,
L 1 and L 2 are independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
n1 is 1,
n2 and n3 are independently an integer of 0 or 1, and
1≤n2+n3≤2;
wherein, in Chemical Formula 2,
L 3 to L 6 and Y 1 are independently, a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
Ar 1 is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
R 7 to R 10 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heterocyclic group, or a combination thereof, and
at least one of R 7 to R 10 and Ar 1 includes a substituted or unsubstituted triphenylene group or a substituted or unsubstituted carbazole group,
wherein, in Chemical Formulae 3 and 4,
Y 2 and Y 3 are independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
Ar 2 and Ar 3 are independently substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
R 11 to R 14 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heterocyclic group, or a combination thereof,
two adjacent *'s of Chemical Formula 3 is combined with two *'s of Chemical Formula 4 to form a fused ring and in Chemical Formula 3, *'s not forming the fused ring are independently CR c , and
R c is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C2 to C12 heterocyclic group, or a combination thereof;
wherein the at least one third compound is selected from the following compounds:
2. The composition for an organic optoelectronic device of claim 1 , wherein Chemical Formula 1 is represented by one of Chemical Formulae 1-I to 1-III:
wherein, in Chemical Formulae 1-I to 1-III,
Z is independently N, C, or CR a ,
at least one of Z is N,
R 1 to R 6 , R 15 to R 28 , and R a are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof,
Ar is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
R 1 to R 6 , R a , R 17 , and R 18 are independently present or adjacent groups are linked to each other to form a ring,
L 1 is a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
n1 is an integer of 1,
n2 is an integer of 0 or 1,
n3 and n4 are independently an integer ranging from 0 to 2,
1≤n2+n3≤2, and
“substituted” refers to replacement of at least one hydrogen by deuterium, a halogen, a hydroxyl group, a C1 to C40 silyl group, a C1 to C30 alkyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heterocyclic group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, or a cyano group.
3. The composition for an organic optoelectronic device of claim 2 , wherein Chemical Formula 1 is represented by Chemical Formula 1-I, and Chemical Formula 1-I is represented by one of Chemical Formulae 1-IA to 1-IC:
wherein, in above Chemical Formulae 1-IA to 1-IC,
Z is independently N, C, or CR a ,
at least one of Z is N,
R 1 to R 6 , R a , R 5a , R 6a , R 5b , R 6b , and R 15 to R 18 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof,
R 1 to R 6 , R a , R 5a , R 6a , R 5b , R 6b , R 17 , and R 18 are independently present or adjacent groups are linked to each other to form a ring,
Ar is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
n1 is an integer of 1,
n2 is an integer of 0 or 1, and
“substituted” refers to replacement of at least one hydrogen by deuterium, a halogen, a hydroxyl group, a C1 to C40 silyl group, a C1 to C30 alkyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heterocyclic group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, or a cyano group.
4. The composition for an organic optoelectronic device of claim 2 , wherein Chemical Formula 1 is represented by Chemical Formula 1-II, and Chemical Formula 1-II is represented by Chemical Formula 1-IIA or 1-IIB:
wherein, in Chemical Formulae 1-IIA and 1-IIB,
Z is independently N, C, or CR a ,
at least one of Z is N,
R 1 to R 6 , R 19 to R 22 , and R a are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof,
R 1 to R 6 , R 19 to R 22 , and R a are independently present or adjacent groups are linked to each other to form a ring,
n1 is an integer of 1,
n2 and n3 are independently an integer of 0 or 1,
1≤n2+n3≤2, and
“substituted” refers to replacement of at least one hydrogen by deuterium, a halogen, a hydroxyl group, a C1 to C40 silyl group, a C1 to C30 alkyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heterocyclic group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, or a cyano group.
5. The composition for an organic optoelectronic device of claim 2 , wherein Chemical Formula 1 is represented by Chemical Formula 1-III, and Chemical Formula 1-III is represented by Chemical Formula 1-IIIA or 1-IIIB:
wherein, in Chemical Formulae 1-IIIA and 1-IIIB,
Z is independently N, C, or CR a ,
at least one of Z is N,
R 1 to R 4 , R 23 to R 28 , and R a are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof,
R 1 to R 4 and R a are independently present or adjacent groups are linked to each other to form a ring,
L 1 is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group or a substituted or unsubstituted terphenylene group,
n1 is an integer of 1,
n2 is an integer of 0 or 1, and
“substituted” refers to replacement of at least one hydrogen by deuterium, a halogen, a hydroxyl group, a C1 to C40 silyl group, a C1 to C30 alkyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heterocyclic group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, or a cyano group.
6. The composition for an organic optoelectronic device of claim 1 , wherein Chemical Formula 2 is represented by one of Chemical Formulae 2-I to 2-III:
wherein, in Chemical Formula 2-I to 2-III,
L 3 to L 6 , Y 1 , and Y 4 are independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
Ar 1 and Ar 4 are independently substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
R 7 to R 10 and R 29 to R 41 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heterocyclic group, or a combination thereof,
m is an integer of 0 to 4, and
“substituted” refers to replacement of at least one hydrogen by deuterium, a halogen, a hydroxyl group, a C1 to C40 silyl group, a C1 to C30 alkyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heterocyclic group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, or a cyano group.
7. The composition for an organic optoelectronic device of claim 6 , wherein Ar 1 and Ar 4 of Chemical Formulae 2-I to 2-III are independently, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted pyridinyl group, or a combination thereof.
8. The composition for an organic optoelectronic device of claim 6 , wherein Chemical Formula 2 is represented by Chemical Formula 2-I, and Chemical Formula 2-I comprises one of structures of Group 3 and the *—Y 1 —Ar 1 , *Y 4 —Ar 4 are one of substituents of Group 4:
[Group 3]
[Group 4]
wherein, in Group 3 and Group 4, * is a linking point.
9. The composition for an organic optoelectronic device of claim 1 , wherein the second compound consists of a combination of the moiety represented by Chemical Formula 3 and the moiety represented by Chemical Formula 4, and the second compound consisting of a combination of the moiety represented by Chemical Formula 3 and the moiety represented by Chemical Formula 4 is represented by at least one of Chemical Formulae 3-I to 3-V:
wherein, in Chemical Formulae 3-I to 3-V,
Y 2 and Y 3 are independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
Ar 2 and Ar 3 are independently substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
R 11 to R 14 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heterocyclic group, or a combination thereof, and
“substituted” refers to replacement of at least one hydrogen by deuterium, a halogen, a hydroxyl group, a C1 to C40 silyl group, a C1 to C30 alkyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heterocyclic group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, or a cyano group.
10. The composition for an organic optoelectronic device of claim 1 , wherein:
the first compound is represented by Chemical Formula 1-I or Chemical Formula 1-III, and
the second compound is represented by Chemical Formula 2-I:
wherein, in Chemical Formulae 1-I and 1-III,
Z is independently N, C, or CR a ,
at least one of Z is N,
R 1 to R 6 , R 15 to R 18 , R 23 to R 28 , and R a are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group,
Ar is independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
R 1 to R 6 , R 15 to R 18 , R 23 to R 28 , and R a are independently present or adjacent groups are linked to each other to form a ring,
L 1 is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted quarterphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted triphenylenyl group, or a substituted or unsubstituted phenanthrenylene group,
n1 is an integer of 1,
n2 and n3 are independently an integer of 0 or 1, and
n4 is an integer ranging from 0 to 2;
wherein, in Chemical Formula 2-I,
L 3 to L 5 , Y 1 , and Y 4 are independently a single bond, or a substituted or unsubstituted C6 to C30 arylene group,
Ar 1 and Ar 4 are independently substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
R 7 to R 9 and R 29 to R 31 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C50 aryl group, and
m is an integer of 0 or 1; and
“substituted” refers to replacement of at least one hydrogen by deuterium, a halogen, a hydroxyl group, a C1 to C40 silyl group, a C1 to C30 alkyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heterocyclic group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, or a cyano group.
11. The composition for an organic optoelectronic device of claim 10 , wherein the first compound is represented by Chemical Formula 1-IB or 1-IIIA:
wherein, in Chemical Formula 1-IB,
Z is independently N, C, or CR a ,
at least one of Z is N,
R 1 to R 4 , R 15 , R 16 , R 5a , R 6a , R 5b , and R 6b are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group,
Ar is independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
R 5a and R 6a and R 5b and R 6b are independently present or adjacent groups are linked to each other to form a ring,
n1 is an integer of 1, and
n2 is an integer of 0 or 1;
wherein, in Chemical Formula 1-IIIA,
Z is independently N, C, or CR a ,
at least one of Z is N,
R 1 to R 4 , R 23 to R 28 and R a are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof,
R 1 to R 4 and R a are independently present or adjacent groups are linked to each other to form a ring,
L 1 is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted quarterphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted triphenylenyl group, or a substituted or unsubstituted phenanthrenylene group,
n1 is an integer of 1,
n2 is an integer of 0 or 1; and
“substituted” refers to replacement of at least one hydrogen by deuterium, a halogen, a hydroxyl group, a C1 to C40 silyl group, a C1 to C30 alkyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heterocyclic group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, or a cyano group.
12. The composition for an organic optoelectronic device of claim 1 , which further comprises a phosphorescent dopant.
13. An organic optoelectronic device comprising
an anode and a cathode facing each other, and
at least one organic layer interposed between the anode and the cathode wherein the organic layer includes the composition for an organic optoelectronic device of claim 1 .
14. A display device comprising the organic optoelectronic device of claim 13 .