Dopant for organic optoelectronic device, organic optoelectronic device and display device

Patent metadata

Field	Value
Publication number	US-10131632-B2
Application number	US-201515571386-A
Country	US
Kind code	B2
Filing date	Oct 26, 2015
Priority date	May 6, 2015
Publication date	Nov 20, 2018
Grant date	Nov 20, 2018

Abstract

The present invention relates to a dopant for an organic optoelectronic device represented by Chemical Formula 1, and to an organic optoelectronic device and a display device comprising the dopant.

First claim

The invention claimed is:

1. A dopant for an organic optoelectronic device represented by Chemical Formula 1:

wherein, in Chemical Formula 1,
W 1 and W 2 are independently a cyano group; a nitro group; an amide group; a sulfonyl group; a phosphine group; a phosphoryl group; a halogen; a C1 to C10 alkyl group substituted with a cyano group, a nitro group, an amide group, a sulfonyl group, a phosphine group, a phosphoryl group, or a halogen; a C6 to C30 aryl group substituted with a cyano group, a nitro group, an amide group, a sulfonyl group, a phosphine group, a phosphoryl group, or a halogen; a C3 to C30 heterocyclic group substituted with a cyano group, a nitro group, an amide group, a sulfonyl group, a phosphine group, a phosphoryl group, or a halogen; or a combination thereof,
D 1 and D 2 are independently a group represented by Chemical Formula 2,
R 1 and R 2 are independently a cyano group; a nitro group; an amide group; a sulfonyl group; a phosphine group; a phosphoryl group; a halogen; a C1 to C10 alkyl group substituted with a cyano group, a nitro group, an amide group, a sulfonyl group, a phosphine group, a phosphoryl group, or a halogen; a C6 to C30 aryl group substituted with a cyano group, a nitro group, an amide group, a sulfonyl group, a phosphine group, a phosphoryl group, or a halogen; a C3 to C30 heterocyclic group substituted with a cyano group, a nitro group, an amide group, a sulfonyl group, a phosphine group, a phosphoryl group, or a halogen; a combination thereof; or a group represented by Chemical Formula 2, and
a, b, c, and d are integers satisfying 0≤a+b≤4 and 0≤c+d≤2, provided that a+b and c+d are not 0 simultaneously,

wherein, in Chemical Formula 2,
X 1 to X 8 are independently N or CR a ,
L 1 is N, B, C, CR b , or SiR c ,
M 1 is a single bond, CR d R e , SiR f R g , NR h , O, or S,
R a is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkenyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C3 to C30 heterocyclic group,
R b to R h are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 carbonyl group, a substituted or unsubstituted C1 to C30 carbonylamino group, a substituted or unsubstituted C1 to C30 sulfamoylamino group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted silyloxy group, a substituted or unsubstituted C1 to C30 acyl group, a substituted or unsubstituted C1 to C20 acyloxy group, a substituted or unsubstituted C1 to C20 acylamino group, a substituted or unsubstituted C1 to C30 sulfonyl group, a substituted or unsubstituted C1 to C30 alkylthiol group, a substituted or unsubstituted C1 to C30 heterocyclothiol group, a substituted or unsubstituted C1 to C30 ureide group, a halogen, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, or a combination thereof, and
is a linking point with Chemical Formula 1.

2. The dopant for an organic optoelectronic device of claim 1 , wherein R 1 is the same as W 1 or D 1 and R 2 is the same as W 2 or D 2 .

3. The dopant for an organic optoelectronic device of claim 2 , wherein the dopant is represented by one of Chemical Formulae 1-I to 1-IV:

wherein, in Chemical Formulae 1-1 to 1-IV,
W 1 and W 2 are independently a cyano group; a nitro group; an amide group; a sulfonyl group; a phosphine group; a phosphoryl group; a halogen; a C1 to C10 alkyl group substituted with a cyano group, a nitro group, an amide group, a sulfonyl group, a phosphine group, a phosphoryl group, or a halogen; a C6 to C30 aryl group substituted with a cyano group, a nitro group, an amide group, a sulfonyl group, a phosphine group, a phosphoryl group, or a halogen; a C3 to C30 heterocyclic group substituted with a cyano group, a nitro group, an amide group, a sulfonyl group, a phosphine group, a phosphoryl group, or a halogen; or a combination thereof,
D 1 and D 2 are independently a group represented by the Chemical Formula 2, and
a, b, c, and d are integers satisfying 0≤a+b≤4 and 0≤c+d≤2, provided that a+b and c+d are not 0 simultaneously.

4. The dopant for an organic optoelectronic device of claim 3 , wherein each of D 1 and W 1 and D 2 and W 2 are linked in an ortho position or each of two D 1 's and two D 2 's are linked in an ortho position.

5. The dopant for an organic optoelectronic device of claim 3 , wherein the total number of D 1 and D 2 is 3 to 5 and the total number of W 1 and W 2 is 1 to 3.

6. The dopant for an organic optoelectronic device of claim 1 , wherein Chemical Formula 2 is represented by one of Chemical Formulae 2-I to 2-VI:

wherein, in Chemical Formulae 2-I to 2-VI,
X 1 to X 8 are independently N or CR a ,
R a is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkenyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C3 to C30 heterocyclic group,
R b , R d , and R c are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 carbonyl group, a substituted or unsubstituted C1 to C30 carbonylamino group, a substituted or unsubstituted C1 to C30 sulfamoylamino group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted silyloxy group, a substituted or unsubstituted C1 to C30 acyl group, a substituted or unsubstituted C1 to C20 acyloxy group, a substituted or unsubstituted C1 to C20 acylamino group, a substituted or unsubstituted C1 to C30 sulfonyl group, a substituted or unsubstituted C1 to C30 alkylthiol group, a substituted or unsubstituted C1 to C30 heterocyclothiol group, a substituted or unsubstituted C1 to C30 ureide group, a halogen, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, or a combination thereof, and
is a linking point with Chemical Formula 1.

7. The dopant for an organic optoelectronic device of claim 1 , wherein two phenyl groups of Chemical Formula 1 are distorted to have an angle of 30 degrees to 70 degrees.

8. The dopant for an organic optoelectronic device of claim 1 , wherein the dopant is a fluorescent dopant havi

Assignees

• Samsung Sdi Co Ltd

Inventors

• Lee Sangshin
• Yu Eun Sun
• Lee Jun Yeob
• Cho Yong Joo

Classifications

• C07D413/14

  containing three or more hetero rings · CPC title

• C07D403/14

  containing three or more hetero rings · CPC title

• C07D417/14

  containing three or more hetero rings · CPC title

• H01L51/5004

  Electricity · mapped topic

• H01L51/0072

  Electricity · mapped topic