Organic electroluminescent compound, a plurality of host materials and organic electroluminescent device comprising the same

Patent metadata

Field	Value
Publication number	US-2025133961-A1
Application number	US-202418794327-A
Country	US
Kind code	A1
Filing date	Aug 5, 2024
Priority date	Aug 29, 2023
Publication date	Apr 24, 2025
Grant date	—

Abstract

The present disclosure relates to an organic electroluminescent compound, a plurality of host materials, and an organic electroluminescent device comprising the same. By comprising the organic electroluminescent compound according to the present disclosure, an organic electroluminescent device having long lifespan properties could be prepared, and by comprising a plurality of host materials according to the present disclosure, an organic electroluminescent device having long lifespan properties could be prepared.

First claim

1 . A plurality of host materials comprising:
a first host material comprising a compound represented by the following formula 1:

wherein,
X 1 and Y 1 each independently represent, —N═, —NR 5 , —O—, or —S—, provided that any one of X 1 and Y 1 is —N═ and the other of X 1 and Y 1 is —NR 5 —, —O—, or —S—;
R 1 represents a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or the following formula 1-a:

wherein,
L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;
Ar 1 represents a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3- to 30-membered)heteroaryl;
Ar 2 represents a substituted or unsubstituted (3- to 30-membered)heteroaryl; and
R 6 each independently represents, hydrogen, deuterium, halogen, 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 fused ring of a (C3-C30)aliphatic ring and a (C6-C30)aromatic ring, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, a substituted or unsubstituted (C1-C30)alkyl(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; or may be linked to an adjacent substituent to form a ring;
R 2 to R 5 each independently represent, hydrogen, deuterium, halogen, 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 fused ring of a (C3-C30)aliphatic ring and a (C6-C30)aromatic ring, or the formula 1-a; or may be linked to an adjacent substituent to form a ring, provided that at least one of R 1 to R 5 is represented by the formula 1-a;
a and b each independently represent an integer of 1 or 2, and c and d each independently represent an integer of 1 to 4; and
when a to d are an integer of 2 or more, each of R 2 to R 4 , and each of R 6 may be the same or different, and

a second host material comprising a compound represented by the following formula 2:

wherein,
X 2 is —O— or —S—;
Ring A is a benzene ring or a naphthalene ring;
R 21 and R 22 each independently represent hydrogen, deuterium, halogen, 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, or a substituted or unsubstituted tri(C6-C30)arylsilyl, or may be linked to an adjacent substituent to form a ring;
L 2 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;
HAr represents a substituted or unsubstituted (3- to 30-membered)heteroaryl containing at least one nitrogen atom;
n is an integer of 1 to 5, and m is an integer of 1 to 4; and
when n and m are an integer of 2 or more, each of R 21 and each of R 22 may be the same or different.

2 . The plurality of host materials according to claim 1 , wherein the substituted alkyl, the substituted aryl(ene), the substituted heteroaryl, the substituted cycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, the fused ring of substituted aliphatic ring and aromatic ring, the substituted mono- or di-alkylamino, the substituted mono- or di-arylamino, the substituted alkylarylamino, the substituted mono- or di-heteroarylamino, and the substituted arylheteroarylamino are each independently substituted with one or more 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, (5- to 30-membered)heteroaryl substituted or unsubstituted with (C6-C30)aryl, (C6-C30)aryl substituted or unsubstituted with (5- to 30-membered)heteroaryl, tri(C1-C30)alkylsilyl, tri(C6-C30)arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C1-C30)alkyldi(C6-C30)arylsilyl, a fused ring of a (C3-C30)aliphatic ring and a (C6-C30)aromatic ring, amino, mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, (C1-C30)alkyl(C6-C30)arylamino, mono- or di-(3- to 30-membered)heteroarylamino, (C1-C30)alkyl(3- to 30-membered)heteroarylamino, (C6-C30)aryl(3- to 30-membered)heteroarylamino, (C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30)arylcarbonyl, (C6-C30)arylphosphinyl, 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 plurality of host materials according to claim 1 , wherein the formula 1 is represented by any one of the following formulas 1-1 to 1-4:

wherein,
c′ is an integer of 1 to 3;
when c′ is an integer of 2 or more, each of R 4 may be the same or different; and
X 1 , Y 1 , R 1 to R 4 , R 6 , L 1 , Ar 1 , Ar 2 , and a to d are the same as defined in claim 1 .

4 . The plurality of host materials according to claim 1 , wherein Ar 2 of the formula 1-a represents any one of following formulas R-1 to R-4:

wherein,
X is O, S, Se, or N; and
R 11 to R 18 may each independently represent, hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl.

5 . The plurality of host materials according to claim 1 , wherein the formula 2 is represented by any one of the following formulas 2-1 to 2-16:

wherein,
L 3 and L 4 may ea

Assignees

• Dupont Specialty Materials Korea Ltd

Inventors

• Jung So-Young
• Lee Hyo-Jung
• Cho Sang-Hee
• Kim Young-Gil
• Park So-Mi
• Kang Hee-Ryong
• Kang Hyun-Ju
• Kim Bitnari
• Jun Ji-Song
• Jeon Yejin
• Han Tae-Jun

Classifications

• C07B59/002

  Heterocyclic compounds · CPC title

• C07D413/12 Primary

  linked by a chain containing hetero atoms as chain links · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• H10K85/60

  Organic compounds having low molecular weight (H10K85/10 - H10K85/50 take precedence) · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title