Organic electroluminescent compound, a plurality of host materials and organic electroluminescent device comprising the same
The present disclosure relates to an organic electroluminescent compound represented by formula 2′, a plurality of host materials comprising at least one first host compound represented by formula 1 and at least one second host compound represented by formula 2, and an organic electroluminescent device comprising the same. By comprising the organic electroluminescent compound or a specific combination of compounds according to the present disclosure as a host material, it is possible to produce an organic electroluminescent device having significantly improved lifetime properties.
1 . A plurality of host materials comprising at least one first host compound and at least one second host compound, wherein the first host compound is represented by the following formula 1, and the second host compound is represented by the following formula 2-2:
in formula 1,
L 1 and L 2 , each independently, represent a single bond, a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted (3- to 30-membered)heteroarylene, or a substituted or unsubstituted (C3-C30)cycloalkylene;
HAr represents a substituted or unsubstituted (3- to 30-membered)heteroaryl;
Ar represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;
R′ 1 to R′ 8 , and R 2 , each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, —NR 13 R 14 , or —SiR 15 R 16 R 17 ; or may be linked to an adjacent substituent(s) to form a ring(s);
R 13 to R 17 , each independently, represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;
with the proviso that at least one of R′ 1 to R′ 8 , and R 2 represents deuterium; and
b represents an integer of 1 or 2, where if b is an integer of 2, each of R 2 may be the same or different from each other:
in formula 2-2,
A 1 represents a phenyl unsubstituted or substituted with at least one selected from the group consisting of deuterium, naphthyl, carbazolyl and 9-phenylcarbazolyl, a deuterium-substituted or unsubstituted dibenzofuranyl, a deuterium-substituted or unsubstituted dibenzothiophenyl, or a carbazolyl unsubstituted or substituted with at least one selected from the group consisting of deuterium and phenyl;
L 3 represents a single bond;
A 3 represents a deuterium-substituted or unsubstituted phenyl, a deuterium-substituted or unsubstituted p-biphenyl, a deuterium-substituted or unsubstituted m-biphenyl, a deuterium-substituted or unsubstituted o-biphenyl, a deuterium-substituted or unsubstituted o-terphenyl, a deuterium-substituted or unsubstituted p-terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted triphenylenyl, a substituted or unsubstituted dimethylfluorenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, or a substituted or unsubstituted carbazolyl;
L 5 represents a single bond, or a deuterium-substituted or unsubstituted (C6-C30)arylene; and
X 11 to X 18 , each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl, and two or more adjacent X 11 to X 18 may be linked to each other to form a ring(s);
at least one of X 11 to X 18 , and X 31 to X 34 represents deuterium or is substituted with deuterium.
2 . The plurality of host materials according to claim 1 , wherein formula 1 is represented by any one of the following formulas 1-1 to 1-6:
in formulas 1-1 to 1-6,
HAr, Ar, L 1 , L 2 , and R′ 1 to R′ 8 are as defined in claim 1 ,
R′ 9 to R′ 12 are as defined for R′ 1 to R′ 8 ,
with the proviso that at least one of R′ 1 to R′ 12 is deuterium.
3 . The plurality of host materials according to claim 1 , wherein formula 2-2 is represented by any one of the following formulas 2-11 to 2-16:
in formulas 2-11 to 2-16,
A 1 , A 3 , L 3S L 5 , X 11 to X 18 , and X 31 to X 34 are as defined in claim 1 .
4 . The plurality of host materials according to claim 1 , wherein the substituent(s) of the substituted alkyl(ene), the substituted aryl(ene), the substituted heteroaryl(ene), the substituted cycloalkyl(ene), the substituted cycloalkenyl, the substituted heterocycloalkyl, the substituted dibenzofuranyl, the substituted dibenzothiophenyl, and the substituted carbazolyl, each independently, are at least one selected from the group consisting of deuterium; a halogen; a cyano; a carboxyl; a nitro; a hydroxyl; a (C1-C30)alkyl; a halo(C1-C30)alkyl; a (C2-C30)alkenyl; a (C2-C30)alkynyl; a (C1-C30)alkoxy; a (C1-C30)alkylthio; a (C3-C30)cycloalkyl; a (C3-C30)cycloalkenyl; a (3- to 7-membered)heterocycloalkyl; a (C6-C30)aryloxy; a (C6-C30)arylthio; a (3- to 30-membered)heteroaryl unsubstituted or substituted with at least one of deuterium and a (C6-C30)aryl(s); a (C6-C30)aryl unsubstituted or substituted with at least one of deuterium, a cyano(s), a (C1-C30)alkyl(s), and a (3- to 30-membered)heteroaryl(s); a tri(C1-C30)alkylsilyl; a tri(C6-C30)arylsilyl; a di(C1-C30)alkyl(C6-C30)arylsilyl; a (C1-C30)alkyldi(C6-C30)arylsilyl; an amino; a mono- or di-(C1-C30)alkylamino; a mono- or di-(C6-C30)arylamino; a (C1-C30)alkyl(C6-C30)arylamino; a (C1-C30)alkylcarbonyl; a (C1-C30)alkoxycarbonyl; a (C6-C30)arylcarbonyl; a di(C6-C30)arylboronyl; a di(C1-C30)alkylboronyl; a (C1-C30)alkyl(C6-C30)arylboronyl; a (C6-C30)aryl(C1-C30)alkyl; and a (C1-C30)alkyl(C6-C30)aryl.
5 . The plurality of host materials according to claim 1 , wherein the compound represented by formula 1 is at least one selected from the group consisting of the following compounds:
in the compounds, Dn represents that n number of hydrogens are replaced with deuterium; and n represents an integer of 1 to 50.
6 . The plurality of host materials according to claim 1 , wherein the compound represented by formula 2-2 is at least one selected from the group consisting of the following compounds:
in the compounds, Dn represents that n number of hydrogens are replaced with deuterium; and n represents an integer of 1 to 50.
7 . An organic electroluminescent device comprising a first electrode, a second electrode, and at least one light-emitting layer between the first electrode and the second electrode, wherein the at least one light-emitting layer comprises the plurality of host materials according to claim 1 .
8 . An organic electroluminescent compound represented by the following formula 2′:
in formula 2′,
A 1 represents a Phenyl unsubstituted or substituted with at least one selected from the group consisting of deuterium, naphthyl, carbazolyl and 9-phenylcarbazolyl, a deuterium-substituted or unsubstituted dibenzofuranyl, a deuterium-substituted or unsubstituted dibenzothiophenyl, or a carbazolyl unsubstituted or substituted with at least one selected from the group consisting of deuterium and phenyl;
L 3 represents a single bond:
A 3 represents a deuterium-substituted or unsubstituted phenyl, a deuterium-substituted or unsubstituted p-biphenyl, a deuterium-substituted or unsubstituted m-biphenyl, a deuterium-substituted or unsubstituted o-biphenyl, a deuterium-substituted or unsubstituted o-terphenyl, a deuterium-substituted or unsubstituted p-terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted triphenylenyl, a substituted or unsubstituted dimethylfluorenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, or a substituted or unsubstituted carbazolyl;
L 5 represents a single bond, or a deuterium-substituted or unsubstituted (C6-C30)arylene; and
X 11 to X 13 , and X 31 to X 34 , each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;
with the proviso that at least one of X 11 , X 15 to X 13 , and X 31 represents deuterium.
9 . The organic electroluminescent compound according to claim 8 , wherein the compound represented by formula 2′ is represented by any one of the following formulas 2′-1 to 2′-6:
in formulas 2′-1 to 2′-6, A 1 , A 3 , L 3 , L 5 , X 11 to X 18 , and X 31 to X 34 are as defined in claim 8 .
10 . The organic electroluminescent compound according to claim 8 , wherein the organic electroluminescent compound represented by formula 2′ is selected from the group consisting of the following compounds:
in the compounds, Dn represents that n number of hydrogens are replaced with deuterium; and n represents an integer of 1 to 50.
11 . An organic electroluminescent device comprising the organic electroluminescent compound according to claim 8 .