Organic electroluminescent device
The present disclosure relates to an organic electroluminescent device comprising a first electrode, a second electrode, and at least one organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises a light-emitting layer and a hole transport zone. By comprising a deuterated compound in at least one of the light-emitting layer and the hole transport zone, it is possible to provide an organic electroluminescent device having improved driving voltage, luminous efficiency, power efficiency, and/or lifetime properties.
1. An organic electroluminescent device comprising a first electrode, a second electrode, and at least one organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises a light-emitting layer and a hole transport zone, and the hole transport zone comprises a deuterated compound; wherein the light-emitting layer comprises a dopant, the dopant comprises at least one selected from the group consisting of a boron derivative, a pyrene derivative, and a benzofluorene derivative.
2. The organic electroluminescent device according to claim 1 , wherein the hole transport zone comprises at least one of a hole auxiliary layer and a light-emitting auxiliary layer.
3. The organic electroluminescent device according to claim 1 , wherein the hole transport zone comprises a compound represented by the following formula 1:
wherein,
Ar 1 to Ar 3 , 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 silyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; with a proviso that at least one of Ar 1 to Ar 3 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;
L 1 to L 3 , each independently, represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;
Dn represents that n hydrogens are replaced with deuterium; and n represents an integer of 0 to 50.
4. The organic electroluminescent device according to claim 3 , wherein at least one of Ar 1 to Ar 3 represents a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted benzofluorenyl, a substituted or unsubstituted triphenylenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenyl.
5. The organic electroluminescent device according to claim 1 , wherein the hole transport zone comprises a compound represented by the following formula 2:
wherein,
ring Z represents a benzene ring or a naphthalene ring;
X 41 represents —O—, —S—, —C(R 51 )(R 52 )—, or —N(R 53 )—;
R 51 and R 52 , each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C2-C30)alkenylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)heteroarylamino, a substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, a substituted or unsubstituted (C1-C30)alkyl(3- to 30-membered)heteroarylamino, a substituted or unsubstituted (C2-C30)alkenyl(C6-C30)arylamino, a substituted or unsubstituted (C2-C30)alkenyl(3- to 30-membered)heteroarylamino, or a substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino; or R 51 and R 52 may be linked to each other to form a ring(s);
R 53 represents hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C2-C30)alkenylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)heteroarylamino, a substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, a substituted or unsubstituted (C1-C30)alkyl(3- to 30-membered)heteroarylamino, a substituted or unsubstituted (C2-C30)alkenyl(C6-C30)arylamino, a substituted or unsubstituted (C2-C30)alkenyl(3- to 30-membered)heteroarylamino, or a substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino;
L 41 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;
Ar 31 represents a substituted or unsubstituted (C6-C30)aryl;
R 41 to R 48 , each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C2-C30)alkenylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)heteroarylamino, a substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, a substituted or unsubstituted (C1-C30)alkyl(3- to 30-membered)heteroarylamino, a substituted or unsubstituted (C2-C30)alkenyl(C6-C30)arylamino, a substituted or unsubstituted (C2-C30)alkenyl(3- to 30-membered)heteroarylamino, or a substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino; or two or more adjacent ones of R 41 to R 48 may be linked to each other to form a ring(s);
Dn represents that n hydrogens are replaced with deuterium; and n represents an integer of 0 to 50.
6. The organic electroluminescent device according to claim 1 , wherein the hole transport zone comprises a compound represented by the following formula 3:
wherein,
ring C, ring D, and ring E, each independently, represent a substituted or unsubstituted benzene ring, or a substituted or unsubstituted naphthalene ring;
Y represents —O—, —S—, or —N(Ra)—;
Ra represents -L 52 -Ar 52 ;
Ar 51 and Ar 52 , each independently, represent a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl containing at least one of nitrogen, oxygen and sulfur, a substituted or unsubstituted di(C6-C30)arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)heteroarylamino, or a substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino;
L 51 and L 52 , each independently, represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;
s represents an integer of 0 or 1;
Dn represents that n hydrogens are replaced with deuterium; and n represents an integer of 0 to 50.
7. The organic electroluminescent device according to claim 1 , wherein the light-emitting layer is a blue light-emitting layer.
8. The organic electroluminescent device according to claim 3 , wherein the compound represented by formula 1 is at least one selected from the following compounds:
9. The organic electroluminescent device according to claim 5 , wherein the compound represented by formula 2 is at least one selected from the following compounds:
10. The organic electroluminescent device according to claim 6 , wherein the compound represented by formula 3 is at least one selected from the following compounds: