IP Library Granted Patent US 9,269,909
Granted Patent B2
US 9,269,909 · App. 13/989,296 · Granted Feb 23, 2016

Electroactive material and devices made with such materials

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Quick Facts
Patent No.
US 9,269,909
App. No.
13/989,296
Granted
Feb 23, 2016
Kind
B2
Abstract

There is provided a compound having Formula I or Formula II where: Ar 1 -Ar 4 are the same or different and are H, D, or aryl.

Claims (37)

1. A compound having Formula I or Formula II

where:

Ar 1 -Ar 4 are the same or different and are hydrocarbon aryls, N-heterocycles, or deuterated-analogs thereof.

2. The compound of claim 1 , wherein at least one of Ar 1 -Ar 4 has a substituent which is, alkyl, aryl, silyl, diarylamine, carbazole, or a deuterated analog thereof.

3. The compound of claim 1 , wherein Ar 1 -Ar 4 have Formula a

where:

R 1 is the same or different at each occurrence and is D, aryl, alkyl, silyl, diarylamino, carbazolyl, or a deuterated analog thereof;

a is the same or different at each occurrence and is an integer from 0-4;

b is an integer from 0-5; and

m is an integer from 1 to 5.

4. The compound of claim 1 , wherein Ar 1 -Ar 4 have Formula b

where:

R 1 is H, D, aryl, alkyl, silyl, diarylamino, carbazolyl, or a deuterated analog thereof, and

m is an integer from 1 to 5;

or a deuterated analog thereof.

5. The compound of claim 1 , wherein Ar 1 -Ar 4 have Formula c

where

R 1 is H, D, aryl, alkyl, silyl, diarylamino, carbazolyl, or a deuterated analog thereof, or a deuterated analog thereof.

6. The compound of claim 1 , wherein one or more of Ar 1 -Ar 4 is phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, pyridine, pyridimine, triazine, or a deuterated analog thereof.

7. The compound of claim 6 , wherein at least one of Ar 1 -Ar 4 is substituted with diarylamino, carbazole, or a deuterated analog thereof.

8. A compound selected from Compound 1 through Compound 8:

9. An electronic device having at least one layer comprising the compound of Formula I or Formula II

where:

Ar 1 -Ar 4 are the same or different and are hydrocarbon aryls, N-heterocycles, or deuterated analogs thereof.

10. The device of claim 9 , wherein the device is an organic thin-film transistor comprising:

a substrate

an insulating layer;

a gate electrode;

a source electrode;

a drain electrode; and

an organic semiconductor layer comprising an electroactive compound having Formula I or Formula II;

wherein the insulating layer, the gate electrode, the semiconductor layer, the source electrode and the drain electrode can be arranged in any sequence provided that the gate electrode and the semiconductor layer both contact the insulating layer, the source electrode and the drain electrode both contact the semiconductor layer and the electrodes are not in contact with each other.

11. The device of claim 9 , wherein the device comprises at least one active layer positioned between two electrical contact layers, wherein the at least one active layer of the device includes a compound having Formula I or Formula II.

12. The device of claim 11 , comprising an anode, a hole injection layer, a photoactive layer, an electron transport layer, and a cathode, wherein at least one of the photoactive layer and the electron transport layer comprises a compound having Formula I or Formula II.

13. The device of claim 12 , wherein the photoactive layer comprises (a) a host material having Formula I or Formula II and (b) an organometallic electroluminescent dopant.

14. The device of claim 13 , wherein the hole injection layer comprises at least one electrically conductive polymer and at least one fluorinated acid polymer.

15. The device of claim 12 , wherein the electron transport layer comprises a compound having Formula I or Formula II.

Assignments (3)
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 May 29, 2013
From: DOGRA, KALINDI; FENNIMORE, ADAM; OLDER, CHRISTINA M.; EAKIN, ROBERT A.
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 030501/0818 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 29, 2013
From: DOGRA, KALINDI; FENNIMORE, ADAM; OLDER, CHRISTINA M.; EAKIN, ROBERT A.
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 030503/0864 →