Organic electroluminescent compound and organic electroluminescent device comprising the same

Patent metadata

Field	Value
Publication number	US-11926591-B2
Application number	US-201916968888-A
Country	US
Kind code	B2
Filing date	Feb 12, 2019
Priority date	Feb 22, 2018
Publication date	Mar 12, 2024
Grant date	Mar 12, 2024

Abstract

The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. By comprising the organic electroluminescent compound of the present disclosure, an organic electroluminescent device having improved driving voltage, luminous efficiency, and/or lifespan characteristics can be provided.

First claim

The invention claimed is:

1. An organic electroluminescent compound represented by the following formula 1:

wherein
Y 1 to Y 14 each independently represent N or CR 1 , in which if a plurality of R 1 's is present, each R 1 may be the same or different;
with the proviso that at least a pair of Y 1 to Y 14 wherein two of Y 1 to Y 14 are adjacent to each other are fused with the following formula 2 to form a ring:

Z represents NR 2 , O, S, CR 3 R 4 or SiR 5 R 6 ;
X 1 to X 4 each independently represent N or CR 7 , in which if a plurality of R 7 's is present, each R 7 may be the same or different;
the dotted line represents a site fused with the adjacent two of Y 1 to Y 14 of formula 1;
R 2 represents

wherein represents the bonding site of La to the nitrogen of NR 2 ;
La represents a single bond, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted (3- to 30-membered)heteroarylene, or a substituted or unsubstituted (C3-C30)cycloalkylene;
Ar 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-(C6-C30)arylamino, a substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino;
R 1 and R 7 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-(C6-C30)arylamino, a substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or adjacent two R 1 's or adjacent two R 7 's may be linked to each other to form a ring;
R 3 to R 6 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; or R 3 and R 4 , or R 5 and R 6 may be linked to each other to form a ring; and
a is an integer of 1 to 4, in which if a is 2 or more, each Ar may be the same or different.

2. The organic electroluminescent compound according to claim 1 , wherein the substituents of the substituted (C1-C30)alkyl, the substituted (C6-C30)aryl(ene), the substituted (3- to 30-membered) heteroaryl(ene), the substituted (C3-C30)cycloalkyl(ene), the substituted (C1-C30)alkoxy, the substituted tri(C1-C30)alkylsilyl, the substituted di(C1-C30)alkyl(C6-C30)arylsilyl, the substituted (C1-C30)alkyldi(C6-C30)arylsilyl, the substituted tri(C6-C30)arylsilyl, the substituted mono- or di-(C1-C30)alkylamino, the substituted mono- or di-(C6-C30)arylamino, the substituted (C6-C30)aryl(3- to 30-membered)heteroarylamino, and the substituted (C1-C30)alkyl(C6-C30)arylamino in La, Ar, R 1 , and R 3 to R 7 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 (5- to 30-membered)heteroaryl unsubstituted or substituted with a (C6-C30)aryl; a (C6-C30)aryl unsubstituted or substituted with a (5- to 30-membered)heteroaryl; 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.

3. The organic electroluminescent compound according to claim 1 , wherein
Z represents NR 2 , O or S;
La represents a single bond, a substituted or unsubstituted (C6-C15)arylene, or a substituted or unsubstituted (5- to 15-membered)heteroarylene;
Ar represents a substituted or unsubstituted (C6-C15)aryl, a substituted or unsubstituted (5- to 15-membered)heteroaryl, a substituted or unsubstituted di(C6-C15)arylamino, or a substituted or unsubstituted (C6-C15)aryl(5- to 15-membered)heteroarylamino;
R 1 represents hydrogen;
R 7 represents hydrogen, a substituted or unsubstituted (C6-C15)aryl, a substituted or unsubstituted (5- to 15-membered)heteroaryl, a substituted or unsubstituted di(C6-C15)arylamino, or a substituted or unsubstituted (C6-C15)aryl(5- to 15-membered)heteroarylamino; and
a is 1 or 2.

4. The organic electroluminescent compound according to claim 1 , wherein
Z represents NR 2 , O or S;
La represents a single bond, an unsubstituted (C6-C15)arylene, or an unsubstituted (5- to 15-membered)heteroarylene;
Ar represents an unsubstituted (C6-C15)aryl, a (5- to 15-membered)heteroaryl unsubstituted or substituted with a (C6-C15)aryl, a di(C6-C15)arylamino unsubstituted or substituted with a (C1-C6)alkyl, or an unsubstituted (C6-C15)aryl(5- to 15-membered)heteroarylamino;
R 1 represents hydrogen;
R 7 represents hydrogen, an unsubstituted (C6-C15)aryl, a (5- to 15-membered)heteroaryl unsubstituted or substituted with a (C6-C15)aryl, a di(C6-C15)arylamino unsubstituted or substituted with a (C1-C6)alkyl, or an unsubstituted (C6-C15)aryl(5- to 15-membered)heteroarylamino; and
a is 1 or 2.

5. The organic electroluminescent compound according to claim 1 , wherein the compound represented by formula 1 is selected from the group consisting of:

Assignees

• Rohm & Haas Elect Materials Korea Ltd

Inventors

• Oh Hong-Se
• Yang Jeong-Eun
• Lee Tae-Jin
• Cho Sang-Hee

Classifications

• C07D209/82 Primary

  Carbazoles; Hydrogenated carbazoles · CPC title

• C07D307/91

  Dibenzofurans; Hydrogenated dibenzofurans · CPC title

• C07D333/76

  Dibenzothiophenes · CPC title

• C07D401/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D401/10

  linked by a carbon chain containing aromatic rings · CPC title