Organic electroluminescent compound and organic electroluminescent device comprising the same
View Patent ↗The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. The organic electroluminescent compound of the present disclosure has a high glass transition temperature that can be used in a deposition process. In addition, an organic electroluminescent device having low driving voltage, a high luminous efficiency and/or long lifespan characteristic can be provided with the use of the organic electroluminescent compound according to the present disclosure.
1. An organic electroluminescent compound represented by the following formula 1:
wherein formula 1,
Z 1 to Z 11 each independently represent CR 1 or N;
R 1 represents hydrogen, deuterium, halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to an adjacent substituent to form a substituted or unsubstituted, (C3-C30) mono- or polycyclic, alicyclic or aromatic ring, or a combination of alicyclic and aromatic rings, whose carbon atom may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur;
L represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene;
Ar represents hydrogen, deuterium, halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)ar(C1-C30)alkyl, —N(R 11 )(R 12 ), —Si(R 13 )(R 14 )(R 15 ), —S(R 16 ), —O(R 17 ), cyano, nitro or hydroxy;
R 11 to R 17 each independently represent hydrogen, deuterium, halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to an adjacent substituent to form a substituted or unsubstituted, (C3-C30) mono- or polycyclic, alicyclic or aromatic ring, or a combination of alicyclic and aromatic rings, whose carbon atom may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur;
the heteroaryl(ene) contains at least one heteroatom selected from B, N, O, S, Si, and P.
2. The organic electroluminescent compound according to claim 1 , wherein R 1 , L, Ar and R 11 to R 17 , the substituents of the substituted (C1-C30)alkyl, the substituted (C6-C30)aryl(ene), the substituted (5- to 30-membered)heteroaryl(ene), the substituted (3- to 7-membered)heterocycloalkyl, the substituted (C3-C30)cycloalkyl, the substituted (C6-C30)ar(C1-C30)alkyl, and the substituted (C3-C30) mono- or polycyclic, alicyclic or aromatic ring, or the combination thereof each independently, represent at least one selected from the group consisting of deuterium; halogen; cyano; carboxyl; nitro; hydroxy; (C1-C30)alkyl; halo(C1-C30)alkyl; (C2-C30)alkenyl, (C2-C30)alkynyl; (C1-C30)alkoxy; (C1-C30)alkylthio, (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl; (3- to 7-membered)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; a (C6-C30)aryl-substituted or unsubstituted (5- to 30-membered)heteroaryl; a (5- to 30-membered)heteroaryl-substituted or unsubstituted (C6-C30)aryl; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; amino; a mono- or di-(C1-C30)alkylamino; a (C1-C30)alky-substituted or unsubstituted mono- or di-(C6-C30)arylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)ar(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl.
3. The organic electroluminescent compound according to claim 1 , wherein,
Z 1 to Z 11 each independently represent CR 1 or N;
R 1 represents hydrogen, or may be linked to an adjacent substituent to form a (C5-C10) mono- or polycyclic, alicyclic or aromatic ring, or a combination of alicyclic and aromatic rings, whose carbon atom may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur;
L represents a single bond, or a substituted or unsubstituted (C6-C20)arylene;
Ar represents a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted (5- to 25-membered)heteroaryl, or —N(R 11 )(R 12 ).
4. The organic electroluminescent compound according to claim 1 , wherein
Z 1 to Z 11 each independently represent CR 1 or N;
R 1 represents hydrogen, or may be linked to an adjacent substituent to form a benzene ring or benzofuran ring;
L represents a single bond, or a (C1-C6)alkyl-substituted or unsubstituted (C6-C20)arylene;
Ar represents an unsubstituted (C6-C20)aryl, at least one (C6-C12)aryl-substituted or unsubstituted (5- to 25-membered)heteroaryl, or —N(R 11 )(R 12 ).
5. The organic electroluminescent compound according to claim 1 , wherein the compound represented by Formula 1 is at least one selected from the group consisting of:
6. An organic electroluminescent material comprising the organic electroluminescent compound according to claim 1 .
7. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1 .
8. The organic electroluminescent device according to claim 7 , wherein the organic electroluminescent compound is comprised in at least one layer of an electron buffer material and an electron transport layer.
9. A display device comprising the organic electroluminescent compound according to claim 1 .