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

Patent metadata

Field	Value
Publication number	US-2024381764-A1
Application number	US-202418594285-A
Country	US
Kind code	A1
Filing date	Mar 4, 2024
Priority date	May 4, 2023
Publication date	Nov 14, 2024
Grant date	—

Abstract

The present disclosure relates to a plurality of host materials, an organic electroluminescent compound, and an organic electroluminescent device comprising the same. An organic electroluminescent device with improved driving voltage, luminous efficiency and/or lifespan properties can be provided by comprising the specific combination of compounds according to the present disclosure as a host material, or by comprising compounds according to the present disclosure.

First claim

1 . A plurality of host materials comprising a first host material comprising a compound represented by the following formula 1 and a second host material comprising a compound represented by the following formula 2:

in formula 1,
R 1 and R 2 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; or may be linked to each other to form a ring(s);
X 1 and Y 1 each independently represent —N═, —NR 14 , —O— or —S—, with a proviso that any one of X 1 and Y 1 represents —N═, and the other of X 1 and Y 1 represents —NR 14 —, —O— or —S—;
ring A and ring B each independently represent a substituted or unsubstituted (C6-C30)arene, or a substituted or unsubstituted (3- to 30-membered)heteroarene;
R 11 to R 14 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 fused ring group of a (C3-C30) aliphatic ring(s) and a (C6-C30) aromatic ring(s), or the following formula 1-1, with a proviso that at least one of R 11 to R 14 is represented by the following formula 1-1;

R 15 each independently 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 fused ring group of a (C3-C30) aliphatic ring(s) and a (C6-C30) aromatic ring(s), or -L 2 -N(Ar 2 )(Ar 3 );
L 1 and L 2 each independently represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;
Ar 1 to Ar 3 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted fused ring group of a (C3-C30) aliphatic ring(s) and a (C6-C30) aromatic ring(s), a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; and
a represents an integer of 1 to 6, b represents an integer of 1 to 8, c represents an integer of 1 to 5, where if a to c are an integer of 2 or more, each of R 12 , each of R 13 , and each of R 15 may be the same as, or different from, each other.

In formula 2,
X 2 represents —O— or —S—;
R 21 and R 22 each independently represent hydrogen, deuterium, or a substituted or unsubstituted (C6-C30)aryl;
L 3 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene;
HAr represents a substituted or unsubstituted (3- to 30-membered)heteroaryl comprising at least one N atom; and
n represents an integer of 1 to 3, m represents an integer of 1 to 4, where if n and m are an integer of 2 or more, each of R 21 and each of R 22 may be the same as, or different from, each other.

2 . The plurality of host materials according to claim 1 , wherein the substituent(s) of the substituted alkyl, the substituted aryl(ene), the substituted heteroaryl(ene), the substituted arene, the substituted heteroarene, the substituted cycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, the substituted fused ring group of an aliphatic ring(s) and an aromatic ring(s), and the substituted alkenyl each independently are at least one selected from the group consisting of deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxy, 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(s), a (C6-C30)aryl unsubstituted or substituted with a (5- 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, a fused ring group of a (C3-C30) aliphatic ring(s) and a (C6-C30) aromatic ring(s), an amino, a mono- or di-(C1-C30)alkylamino, a mono- or di-(C2-C30)alkenylamino, a (C1-C30)alkyl(C2-C30)alkenylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, a (C1-C30)alkyl(C6-C30)arylamino, a mono- or di-(3- to 30-membered)heteroarylamino, a (C1-C30)alkyl(3- to 30-membered)heteroarylamino, a (C2-C30)alkenyl(C6-C30)arylamino, a (C2-C30)alkenyl(3- to 30-membered)heteroarylamino, a (C6-C30)aryl(3- to 30-membered)heteroarylamino, a (C1-C30)alkylcarbonyl, a (C1-C30)alkoxycarbonyl, a (C6-C30)arylcarbonyl, a (C6-C30)arylphospinyl, 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 plurality of host materials according to claim 1 , wherein formula 1 is represented by one of the following formulas 3 and 4:

in formulas 3 and 4,
R 1 , R 2 , R 11 to R 13 , X 1 , Y 1 , and L 1 , are as defined in claim 1 , a represents an integer of 1 or 2, and b represents an integer of 1 to 6.

4 . The plurality of host materials according to claim 1 , wherein formula 1 is represented by one of the following formulas 5 to 8:

in formulas 5 to 8,
Ar 4 and Ar 5 each independently represent a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;
X 2 , R 21 and R 22 , L 3 , n, m are as defined in claim 1 .

5 . The plurality of host materials according to claim 1 , wherein the compound represented by formula 1 is at least one selected from the following compounds:

Assignees

• Rohm & Haas Elect Materials Korea Ltd

Inventors

• Yang Jeong-Eun
• Lee Ga-Won
• Kang Hee-Ryong
• Park Hyo-Soon
• Cho Sang-Hee
• Jeon Jeong-Hwan

Classifications

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title

• C09K2211/1037

  with sulfur · CPC title

• C09K2211/1033

  with oxygen · CPC title