IP Library › Granted Patent US 10,131,632
Granted Patent B2
US 10,131,632 · App. 15/571,386 · Granted Nov 20, 2018

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

Inventors: Sangshin Lee (Suwon-si, KR); Eun Sun Yu (Suwon-si, KR); Jun Yeob Lee (Suwon-si, KR); Yong Joo Cho (Suwon-si, KR)
Assignee: Samsung SDI Co., Ltd.
C07D209/82C07D403/10C07D403/14C07D413/14C07D417/14H01L51/0072H01L51/5004H01L51/5016
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Quick Facts
Patent No.
US 10,131,632
App. No.
15/571,386
Granted
Nov 20, 2018
Kind
B2
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.

Claims (42)

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 having a maximum light-emitting wavelength (λ max ) of 380 nm to 580 nm.

9. The dopant for an organic optoelectronic device of claim 1 , wherein the dopant is a fluorescent dopant having an energy gap between singlet energy and triplet energy of less than or equal to 0.2 eV.

10. The dopant for an organic optoelectronic device of claim 1 , wherein the dopant represented by Chemical Formula 1 is one of compounds of Group 1:

11. An organic optoelectronic device, comprising

an anode and a cathode facing each other, and

an organic layer between the anode and the cathode

wherein the organic layer includes

at least one host, and

the dopant of claim 1 .

12. The organic optoelectronic device of claim 11 , wherein the dopant is a fluorescent dopant having a maximum light-emitting wavelength (λ max ) in 380 nm to 580 nm.

13. The organic optoelectronic device of claim 11 , wherein the host is selected from compounds having a larger energy bandgap between HOMO and LUMO than the dopant.

14. The organic optoelectronic device of claim 11 , wherein the dopant is included in an amount of 0.01 wt % to 40 wt % based on a total amount of the host and the dopant.

15. The organic optoelectronic device of claim 11 , wherein the organic optoelectronic device has a light-emitting full width at half maximum (FWHM) of 10 nm to 100 nm.

16. A display device comprising the organic optoelectronic device of claim 11 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 2, 2017
From: LEE, SANGSHIN; YU, EUN SUN; LEE, JUN YEOB; CHO, YONG JOO
To: SAMSUNG SDI CO., LTD.
Reel/Frame 044020/0529 →
Priority Claims (1)
KR 10-2015-0063365 · May 6, 2015 · national
Continuity (1)
Related Publication 20180215711A1 · Aug 2, 2018
Cited By (1)
US 12,262,635