Method for preparation of deuterated anthracene compound, reaction composition, deuterated anthracene compound, and composition

Patent metadata

Field	Value
Publication number	US-2024083865-A1
Application number	US-202218265754-A
Country	US
Kind code	A1
Filing date	Jan 28, 2022
Priority date	Feb 4, 2021
Publication date	Mar 14, 2024
Grant date	—

Abstract

Provided is a method for preparing a deuterated anthracene compound, the method including synthesizing a deuterated anthracene compound by reacting a halogenated benzene having at least one deuterium with an enolate. Also provided is a reaction composition; a deuterated anthracene compound; and a composition containing the deuterated anthracene compound.

First claim

1 . A method for preparing a deuterated anthracene compound, the method comprising:
synthesizing a deuterated anthracene compound by reacting a halogenated benzene having at least one deuterium with an enolate of Chemical Formula 1:

2 . (canceled)

3 . The method of claim 1 , wherein the halogenated benzene having at least one deuterium is halogenated benzene-d5.

4 . The method of claim 1 , wherein the deuterated anthracene compound is a compound of the following Chemical Formula 2:

wherein in Chemical Formula 2, b is an integer from 1 to 8.

5 . The method of claim 2 , wherein the method comprises synthesizing a compound of the following Chemical Formula 3 using a solution comprising the compound of Chemical Formula 2 and a first halogen supplying agent; and
synthesizing a compound of the following Chemical Formula 4 by reacting the compound of Chemical Formula 3 with L1-Ar1:

wherein in Chemical Formulae 3 and 4:
X1 is a halogen group;
L1 is a leaving group;
Ar1 is deuterium a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; and
b is an integer from 1 to 8.

6 . The method of claim 5 , wherein the method comprises synthesizing a compound of the following Chemical Formula 5 using a solution comprising the compound of Chemical Formula 4 and a second halogen supplying agent; and
synthesizing a compound of the following Chemical Formula 6 by reacting the compound of Chemical Formula 5 with L2-Ar2:

wherein in Chemical Formulae 5 and 6:
X2 is a halogen group;
L2 is a leaving group;
Ar1 and Ar2 are the same as or different from each other, and are each independently deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; and
b is an integer from 1 to 8.

7 . The method of claim 1 , further comprising synthesizing a halogenated benzene having at least one deuterium from benzene-d6 using a third halogen supplying agent before the synthesizing of the compound.

8 . The method of claim 1 , wherein the enolate of Chemical Formula 1 is formed from the following Chemical Formula 7 or 8:

wherein in Chemical Formulae 7 and 8:
L3 and L4 are the same as or different from each other, and are each independently a leaving group.

9 . The method of claim 1 , wherein the enolate of Chemical Formula 1 is formed from trimethyl(vinyloxy)silane or acetaldehyde.

10 . The method of claim 2 , wherein the synthesizing of the compound of Chemical Formula 2 synthesizes the compound of Chemical Formula 2 using a solution comprising halogenated benzene-d5, the compound of Chemical Formula 7 or 8, a base, an alkyllithium, and a solvent:

wherein in Chemical Formulae 7 and 8:
L3 and L4 are the same as or different from each other, and are each independently a leaving group.

11 . The method of claim 5 , whe

wherein b is an integer from 1 to 8.

12 . The method of claim 6 , wherein Chemical Formula 5 is any one of the following structures:

wherein b is an integer from 1 to 8.

13 . The method of claim 6 , wherein Chemical Formula 6 is any one of the following structures:

Assignees

• Lg Chemical Ltd

Inventors

• Jung Changyoung
• Kim Sunmin
• Lee Woochul
• Jeong Kyung Seok
• Kim Woo Han
• Kim Changmin

Classifications

• C07D307/91 Primary

  Dibenzofurans; Hydrogenated dibenzofurans · CPC title

• C07B59/001 Primary

  Acyclic or carbocyclic compounds · CPC title

• C07B59/002

  Heterocyclic compounds · CPC title

• C07C15/28

  Anthracenes · CPC title

• C07D209/86

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system · CPC title