IP Library Granted Patent US 9,793,497
Granted Patent B2
US 9,793,497 · App. 14/386,137 · Granted Oct 17, 2017

Green luminescent materials

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Quick Facts
Patent No.
US 9,793,497
App. No.
14/386,137
Granted
Oct 17, 2017
Kind
B2
Abstract

There is provided a compound having Formula I In the formula: Ar can be phenyl, biphenyl, or terphenyl, and can optionally have one or more substituents which can be D, alkyl, silyl, deuterated alkyl, or deuterated silyl; R 1 can be alkyl, silyl, aryl, heteroaryl, deuterated alkyl, deuterated silyl, deuterated aryl, or deuterated heteroaryl; R 2 -R 11 are the same or different and can be H, D, alkyl, silyl, deuterated alkyl, or deuterated silyl.

Claims (24)

1. An organic electronic device comprising a first electrical contact, a second electrical contact, and a photoactive layer therebetween, wherein the photoactive layer comprises a luminescent compound having red, orange, or yellow emission color, a host material, and a compound having Formula I

wherein:

Ar is selected from the group consisting of phenyl, biphenyl, and terphenyl, wherein Ar optionally has one or more substituents selected from the group consisting of D, alkyl, silyl, deuterated alkyl, and deuterated silyl;

R 1 is selected from the group consisting of H, D, alkyl, silyl, aryl, heteroaryl, deuterated alkyl, deuterated silyl, deuterated aryl, and deuterated heteroaryl; and

R 2 -R 11 are the same or different and are selected from the group consisting of H, D, alkyl, silyl, deuterated alkyl, and deuterated silyl;

wherein the compound having Formula I is present as a hole-trap material which possesses a highest occupied molecular orbital (HOMO) lying closer in energy to the vacuum level than the HOMO of any other material present in the photoactive layer.

2. An organic electronic device comprising a first electrical contact, a second electrical contact, and a photoactive layer therebetween, wherein the photoactive layer comprises a luminescent compound having red, orange, or yellow emission color, a host material, and a compound having Formula I

wherein:

Ar is selected from the group consisting of phenyl, biphenyl, and terphenyl, wherein Ar optionally has one or more substituents selected from the group consisting of D, alkyl, silyl, deuterated alkyl, and deuterated silyl;

R 1 is selected from the group consisting of H, D, alkyl, silyl, aryl, heteroaryl, deuterated alkyl, deuterated silyl, deuterated aryl, and deuterated heteroaryl; and

R 2 -R 11 are the same or different and are selected from the group consisting of H, D, alkyl, silyl, deuterated alkyl, and deuterated silyl;

wherein the compound having Formula I is present as an electron-trap material which possesses a lowest unoccupied molecular orbital (LUMO) lying further in energy from the vacuum level than the LUMO of any other material present in the photoactive layer.

3. The device of claim 1 , wherein the hole-trap material is present in an amount of 1-10 wt % based on the total weight of the photoactive layer.

4. The device of claim 1 , wherein the hole-trap material is selected from compounds G1 through G6, G8, G11 through G13, and G15 through G17

5. The device of claim 2 , wherein the electron-trap material is present in an amount of 1-10 wt % based on the total weight of the photoactive layer.

6. The device of claim 2 , wherein the electron-trap material is selected from compounds G1 through G6, G8, G11 through G13, and G15 through G17

7. The device of claim 1 , wherein Ar is selected from the group consisting of phenyl, 3-biphenyl, 4-biphenyl, 4,4′-terphenyl, 4,3′-terphenyl, 3,4′-terphenyl, 3,3′-terphenyl, 3,5-terphenyl, 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, and deuterated analogs thereof.

8. The device of claim 1 , wherein R 1 is selected from the group consisting of alkyl having 1-20 carbons, silyl, deuterated alkyl having 1-20 carbons, and deuterated silyl.

9. The device of claim 1 , wherein R 1 is selected from the group consisting of phenyl, naphthyl, biphenyl, terphenyl, substituted derivatives thereof, and deuterated analogs thereof.

10. The device of claim 1 , wherein R 1 is selected from the group consisting of carbazolyl, phenyl-substituted carbazolyl, alkyl-substituted carbazolyl, and deuterated analogs thereof.

11. The device of claim 2 , wherein Ar is selected from the group consisting of phenyl, 3-biphenyl, 4-biphenyl, 4,4′-terphenyl, 4,3′-terphenyl, 3,4′-terphenyl, 3,3′-terphenyl, 3,5-terphenyl, 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, and deuterated analogs thereof.

12. The device of claim 2 , wherein R 1 is selected from the group consisting of alkyl having 1-20 carbons, silyl, deuterated alkyl having 1-20 carbons, and deuterated silyl.

13. The device of claim 2 , wherein R 1 is selected from the group consisting of phenyl, naphthyl, biphenyl, terphenyl, substituted derivatives thereof, and deuterated analogs thereof.

14. The device of claim 2 , wherein R 1 is selected from the group consisting of carbazolyl, phenyl-substituted carbazolyl, alkyl-substituted carbazolyl, and deuterated analogs thereof.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 22, 2019
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: LG CHEM, LTD.
Reel/Frame 050150/0482 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 22, 2014
From: HERRON, NORMAN; GAO, WEIYING
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 033785/0429 →