IP Library › Granted Patent US 10,586,933
Granted Patent B2
US 10,586,933 · App. 15/113,501 · Granted Mar 10, 2020

Electroactive metal complexes

Inventors: Norman Herron (Newark, DE); Adam Fennimore (Wilmington, DE)
Assignee: LG Chem, Ltd.
H01L51/0085C07F15/0033C09K11/025C09K11/06H01L51/0072C09K2211/1007C09K2211/1044C09K2211/185H01L51/5016
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Quick Facts
Patent No.
US 10,586,933
App. No.
15/113,501
Granted
Mar 10, 2020
Kind
B2
Abstract

Disclosed is a compound having Formula I In Formula I: Ar is aryl or deuterated aryl; R 1 and R 2 are the same or different and can be alkyl, silyl, aryl, deuterated alkyl, deuterated silyl, or deuterated aryl; R 3 -R 5 are the same or different at each occurrence and can be D, alkyl, silyl, aryl, deuterated alkyl, deuterated aryl, or deuterated silyl; where two adjacent R 4 groups can be joined together to form a fused 6-membered aromatic or deuterated aromatic ring; a and c are independently an integer from 0-3; and b is an integer from 0-4. Formula I may exist as either fac or mer structural isomers including mixtures of both.

Claims (44)

1. A compound having Formula I

wherein:

Ar is aryl or deuterated aryl;

R 1 and R 2 are the same or different and are selected from the group consisting of alkyl, silyl, aryl, deuterated alkyl, deuterated silyl, and deuterated aryl;

R 3 -R 5 are the same or different at each occurrence and are selected from the group consisting of D, alkyl, silyl, aryl, deuterated alkyl, deuterated aryl, and deuterated silyl; where two adjacent R 4 groups can be joined together to form a fused 6-membered aromatic or deuterated aromatic ring;

a and c are independently an integer from 0-3;

b is an integer from 0-4; and

the compound of Formula I emits light via photoluminescence using an exciting wavelength ranging from 300 to 360 nm, the emitted light having an emission profile over a range of wavelength, the full width at half the maximum intensity (FWHM) of the emission profile is less than or equal to 60 nm.

2. The compound of claim 1 , wherein the compound exists as the isomer selected from the group consisting of fac structural isomer, mer structural isomer, and mixtures thereof.

3. The compound of claim 1 , wherein Ar is selected from the group consisting of phenyl, 3-biphenyl, 4-biphenyl, 4,4′-terphenyl, 4,3′-terphenhyl, 3,4′-terphenyl, 3,3′-terphenyl, 3,5-terphenyl, 1-naphthyl, 2-naphthyl, 4-(1-naphthyl)phenyl, 4-(2-naphthyl)phenyl, 3-(1-naphthyl)phenyl, 3-(2-naphthyl)phenyl, substituted phenyl, substituted 3-biphenyl, substituted 4-biphenyl, substituted 4,4′-terphenyl, substituted 4,3′-terphenyl, substituted 3,4′-terphenyl, substituted 3,3′-terphenyl, substituted 3,5′-terphenyl, substituted 1-naphthyl, substituted 2-naphthyl, substituted 4-(1-naphthyl)phenyl, substituted 4-(2-naphthyl)phenyl, substituted 3-(1-naphthyl)phenyl, substituted 3-(2-naphthyl)phenyl, and deuterated analogs thereof.

4. The compound of claim 1 , wherein R 1 and R 2 are independently selected from the group consisting of linear alkyl having 1-10 carbons, branched alkyl having 3-10 carbons, cycloalkyl having 6-10 ring carbons, silyl and deuterated analogs thereof.

5. The compound of claim 1 , wherein R 1 and R 2 are independently selected from the group consisting of phenyl, naphthyl, biphenyl, terphenyl, substituted derivatives thereof, and deuterated analogs thereof.

6. The compound of claim 1 , wherein a=b=c=0.

7. The compound of claim 1 , wherein a>0 and R 3 is selected from the group consisting of D, alkyl having 1-10 carbons, and deuterated alkyl having 1-10 carbons.

8. The compound of claim 1 , wherein b>0 and R 4 is selected from the group consisting of D, alkyl having 1-10 carbons, and deuterated alkyl having 1-10 carbons.

9. The compound of claim 1 , wherein c>0 and R 5 is selected from the group consisting of D, alkyl having 1-10 carbons, and deuterated alkyl having 1-10 carbons.

10. The compound of claim 1 , wherein the compound of Formula I is represented by Formula II

wherein

Ar is aryl or deuterated aryl;

R 1 and R 2 are the same or different and are selected from the group consisting of alkyl, silyl, aryl, deuterated alkyl, deuterated silyl, and deuterated aryl;

R 3 , R 5 and R 6 are the same or different at each occurrence and are selected from the group consisting of D, alkyl, silyl, aryl, deuterated alkyl, deuterated aryl, and deuterated silyl;

a and c are independently an integer from 0-3; and

d is an integer from 0-6.

11. The compound of claim 10 , wherein the compound exists as the isomer selected from the group consisting of fac structural isomer, mer structural isomer, and mixtures thereof.

12. The compound of claim 1 , wherein the compound is selected from compound 1 through compound 15

13. An organic electronic device comprising a first electrical contact, a second electrical contact and a photoactive layer therebetween, the photoactive layer comprising a compound having Formula I

wherein:

Ar is aryl or deuterated aryl;

R 1 and R 2 are the same or different and are selected from the group consisting of alkyl, silyl, aryl, deuterated alkyl, deuterated silyl, and deuterated aryl;

R 3 -R 5 are the same or different at each occurrence and are selected from the group consisting of D, alkyl, silyl, aryl, deuterated alkyl, deuterated aryl, and deuterated silyl; where two adjacent R 4 groups can be joined together to form a fused 6-membered aromatic or deuterated aromatic ring;

a and c are independently an integer from 0-3; and

b is an integer from 0-4; and

the compound of Formula I emits light via photoluminescence using an exciting wavelength ranging from 300 to 360 nm, the emitted light having an emission profile over a range of wavelength, the full width at half the maximum intensity (FWHM) of the emission profile is less than or equal to 60 nm.

14. The device of claim 13 , wherein the photoactive layer comprises the compound of Formula I and further comprises a host material.

15. The device of claim 13 , wherein the photoactive layer comprises a luminescent compound, a host material, and a compound having Formula I as a hole-trap material or an electron-trap material.

16. The device of claim 13 , wherein the compound of Formula I is represented by Formula II

wherein:

Ar is aryl or deuterated aryl;

R 1 and R 2 are the same or different and are selected from the group consisting of alkyl, silyl, aryl, deuterated alkyl, deuterated silyl, and deuterated aryl;

R 3 , R 5 , and R 6 are the same or different at each occurrence and is selected from the group consisting of D, alkyl, silyl, aryl, deuterated alkyl, deuterated aryl, and deuterated silyl;

a and c are independently an integer from 0-3; and

d is an integer from 0-6.

17. The device of claim 16 , wherein the photoactive layer comprises the compound of Formula II and further comprises a host material.

18. The device of claim 16 , wherein the photoactive layer comprises a luminescent compound, a host material, and a compound having Formula II as a hole-trap material or an electron-trap material.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 20, 2019
From: E.I. DU PONT DE NEMOURS AND COMPANY
To: LG CHEM, LTD.
Reel/Frame 049226/0488 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 13, 2016
From: HERRON, NORMAN; FENNIMORE, ADAM
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 039712/0073 →
Continuity (2)
Provisional Application 61930789 · Jan 23, 2014
Related Publication 20170012222A1 · Jan 12, 2017