Blue luminescent composition and organic electroluminescent device comprising blue luminescent composition

Patent metadata

Field	Value
Publication number	US-12410367-B2
Application number	US-202519053440-A
Country	US
Kind code	B2
Filing date	Feb 14, 2025
Priority date	Oct 30, 2024
Publication date	Sep 9, 2025
Grant date	Sep 9, 2025

Abstract

The present invention discloses a blue luminescent composition and an organic electroluminescent device comprising the blue luminescent composition. The blue luminescent composition comprises a host material with a general structural formula as represented by Formula I and a guest material with a general structural formula as represented by Formula II. In the present invention, a composition composed by rational combination of a compound containing a dibenzofuran group and deuterium-substituted anthracene as a host material and a compound containing a cycloalkyl group and a steric hindrance group such as thiophene as a guest material is capable of significantly enhancing the stability and lifetime of a blue-light organic electroluminescent device while enhancing the electron migration and transfer efficiency and eliminating a host luminescence phenomenon.

First claim

We claim:

1. A blue luminescent composition, characterized in that the blue luminescent composition comprises a compound with a general structural formula as represented by Formula I and a compound with a general structural formula as represented by Formula II:

wherein in the Formula I,
Ar 1 represents one of a deuterium-substituted or unsubstituted phenyl group, a deuterium-substituted or unsubstituted naphthyl group, a deuterium-substituted or unsubstituted phenanthryl group, or a deuterium-substituted or unsubstituted pyrenyl group;
L 1 represents one of a single bond, a deuterium-substituted or unsubstituted phenylene group, and a deuterium-substituted or unsubstituted naphthylene group;

Ar 2 represents
R 11 to R 14 and R 21 to R 24 each independently represent hydrogen or deuterium;
any one of R 11 to R 14 and R 21 to R 24 is bonded to the anthracene structure in Formula I; and
when any one of R 11 to R 14 is selected from deuterium, none of R 21 to R 24 is selected from deuterium; when none of R 11 to R 14 is selected from deuterium, at least one of R 21 to R 24 is selected from deuterium; and when any one of R 11 to R 14 and R 21 to R 24 is selected from deuterium, hydrogens in the same benzene ring to which the deuterium belongs are all replaced by deuterium; and
in Formula II,
ring A represents a substituted or unsubstituted cycloalkyl group with a carbon atom number of 3 to 10; and La represents a single bond;
R 1 , R 2 , R 3 , and R 5 each independently represent any one of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group with a carbon atom number of 1 to 30, a substituted or unsubstituted alkenyl group with a carbon atom number of 2 to 30, a substituted or unsubstituted cycloalkyl group with a carbon atom number of 3 to 30, a substituted or unsubstituted aryl group with a carbon atom number of 6 to 60, a substituted or unsubstituted heteroaryl group with a carbon atom number of 5 to 60, a substituted or unsubstituted fused cyclic aryl group with a carbon atom number of 5 to 60, a substituted or unsubstituted fused cyclic heteroaryl group with a carbon atom number of 5 to 60, and a substituted or unsubstituted amino group; two or more of R 1 , R 2 , R 3 , and R 5 can be connected to each other to form a cyclic structure;
R 4 represents any one of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group with a carbon atom number of 1 to 30, a substituted or unsubstituted alkoxy group with a carbon atom number of 1 to 30, a substituted or unsubstituted cycloalkyl group with a carbon atom number of 3 to 30, a substituted or unsubstituted aryl group with a carbon atom number of 6 to 60, a substituted or unsubstituted heteroaryl group with a carbon atom number of 5 to 60, a substituted or unsubstituted fused cyclic aryl with a carbon atom number of 5 to 60, a substituted or unsubstituted fused cyclic heteroaryl with a carbon atom number of 5 to 60, and a substituted or unsubstituted amino group;
X represents O or S;
m, n, and q each independently represent 0, 1, 2, 3, or 4; when m represents 2, 3, or 4, R 1 can be the same or different; when n represents 2, 3, or 4, R 2 can be the same or different; and when q represents 2, 3, or 4, R 5 can be the same or different;
p represents 0, 1, 2, 3, 4, or 5; and when p represents 2, 3, 4, or 5, R 5 can be the same or different;
r represents 0 or 1;
substituents in ring A, R 1 , R 2 , R 3 , R 4 , and R 5 can be the same or different and are each independently selected from one of deuterium, halogen, cyano, an alkyl group with a carbon atom number of 1 to 10, an aryl group with a carbon atom number of 6 to 60, a heteroaryl group with a carbon atom number of 5 to 60, a fused cyclic aryl group with a carbon atom number of 5 to 60, a cycloalkyl group with a carbon atom number of 3 to 30, and amino, wherein two or more of the substituents can be connected to each other to form an aliphatic ring, an aromatic ring, or a fused ring; and
in Formulas I and II, any hydrogen can be replaced by deuterium, any nitrogen can be replaced by 15 N, any sulfur can be replaced by 33 S, 34 S, or 36 S, any oxygen can be replaced by 17 O or 18 O, any carbon can be replaced by 13 C, and any boron can be replaced by 11 B.

2. The blue luminescent composition according to claim 1 , characterized in that when L 1 represents a single bond, Ar 1 represents one of a deuterium-substituted or unsubstituted phenyl group, a deuterium-substituted or unsubstituted naphthyl group, a deuterium-substituted or unsubstituted phenanthryl group, and a deuterium-substituted or unsubstituted pyrenyl group;
when L 1 represents phenylene, Ar 1 represents phenyl or naphthyl;
when L 1 represents a deuterium-substituted phenylene group, Ar 1 represents a deuterium-substituted phenyl group or a deuterium-substituted naphthyl group;
when L 1 represents naphthylene, Ar 1 represents phenyl; and
when L 1 represents a deuterium-substituted naphthylene group, Ar 1 represents a deuterium-substituted phenyl group.

3. The blue luminescent composition according to claim 1 , characterized in that Ar 2 is selected from one of structures represented by Formulas A-1 to A-8 below:

wherein
* represents a site at which Ar 2 is bonded to the anthracene structure in Formula I.

4. The blue luminescent composition according to claim 1 , characterized in that the compound represented by Formula II is selected from any one of Formulas II-1 to II-4:

5. The blue luminescent composition according to claim 4 , characterized in that R 1 , R 2 , R 3 , and R 5 each independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group with a carbon atom number of 1 to 10, a substituted or unsubstituted alkenyl group with a carbon atom number of 2 to 10, a substituted or unsubstituted cycloalkyl group with a carbon atom number of 3 to 10, and a substituted or unsubstituted aryl group with a carbon atom number of 6 to 12, wherein two or more of R 1 , R 2 , R 3 , and R 5 can be connected to each other to form a cyclic structure;
R 4 represents hydrogen, deuterium, a substituted or unsubstituted alkyl group with a carbon atom number of 1 to 10, a substituted or unsubstituted cycloalkyl group with a carbon atom number of 3 to 10, and a substituted or unsubstituted aryl group with a carbon atom number of 6 to 12; and
substituents in ring A, R 1 , R 2 , R 3 , R 4 , and R 5 can be the same or different and are each independently selected from deuterium and an alkyl group with a carbon atom number of 1 to 10.

6. The blue luminescent composition according to claim 4 , characterized in that the cycloalkyl group represents cyclohexyl or cyclopentyl.

7. The blue luminescent composition according to claim 1 , characterized in that R 1 , R 2 , R 3 , and R 5 each independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group with a carbon atom number of 1 to 10, a substituted or unsubstituted alkenyl group with a carbon atom number of 2 to 10, a substituted or unsubstituted cycloalkyl group with a carbon atom number of 3 to 10, and a substituted or unsubstituted aryl group with a carbon atom number of 6 to 12, wherein

Assignees

• Shijiazhuang Chengzhi Yonghua Display Materials Co Ltd

Inventors

• Zheng Zaihao
• Bu Pengjun
• Yue Shiwen
• Cao Zhicheng
• Zhang Zenglin

Classifications

• C09K2211/1018

  Heterocyclic compounds · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K11/02

  Use of particular materials as binders, particle coatings or suspension media therefor · CPC title

• H10K85/626

  containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene · CPC title