Method of making sulfide compounds

• US 9,181,270 B2
• Filed: 02/28/2014
• Issued: 11/10/2015
• Est. Priority Date: 02/28/2014
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Joseph, Scott, Xia, Chuanjun, Dyatkin, Alexey Borisovich
• Primary Examiner(s): Leeser, Erich A
• Application Number:
  US14/193,771
• Publication Number:
  US 20150246928A1
• Time in Patent Office: 620 Days
• US Class Current: 1/1
• CPC Class Codes: C07D 213/70 Sulfur atoms
• CPC Class Codes: C07D 239/30 Halogen atoms or nitro radicals
• CPC Class Codes: C07D 495/04 Ortho-condensed systems
• CPC Class Codes: H10K 85/654 comprising only nitrogen as heteroatom H10K85/652 takes precedence
• CPC Class Codes: H10K 85/657 Polycyclic condensed heteroaromatic hydrocarbons

Abstract

According to one embodiment of the present disclosure, a method of making sulfide compounds using Scheme 1

is disclosed. In Scheme 1, X¹, X², and X³ are independently selected from the group consisting of F, Cl, Br, and I; Y is selected from the group consisting of Cl, Br, and I; and R¹ and R² are independently selected from the group consisting of alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, alkyl, aryl, and heteroaryl, wherein R¹ and R² may be further substituted, and wherein R¹ is optionally covalently linked to R² and the reaction is intramolecular. In some embodiments, no catalyst is used in Scheme 1.

Claims

1. A method comprising Scheme 1:

2. The method of claim 1, wherein R¹ and R² are independently selected from the group consisting of aryl, substituted aryl, heteroaryl, and substituted heteroaryl.

3. The method of claim 2, wherein R² is heteroaryl with a N heteroatom ortho to Y.

4. The method of claim 1, wherein R² is heteroaryl with a N heteroatom ortho to Y.

5. The method of claim 1, wherein R¹ and R² are independently selected from the group consisting of phenyl, substituted phenyl, pyridyl, substituted pyridyl, pyrimidyl, and substituted pyrimidyl.

6. The method of claim 1, wherein R² is pyridyl, substituted pyridyl, pyrimidyl, and substituted pyrimidyl, with a N heteroatom ortho to Y.

7. The method of claim 1, wherein X¹, X², and X³ are Cl.

8. The method of claim 1, wherein Y is Cl or Br.

9. The method of claim 1, wherein X¹, X², and X³ are Cl, and Y is Cl or Br.

10. The method of claim 1, wherein R¹ is covalently linked to R² and the reaction is intramolecular.

11. The method of claim 1, wherein R¹ is not covalently linked to R².

12. The method of claim 1, further comprising a catalyst selected from the group consisting of transition metal complexes.

13. The method of claim 12, wherein said transition metal complex comprises at least one metal precursor or ligand.

14. The method of claim 12, wherein said transition metal complex is formed in situ.

15. The method of claim 12, wherein the catalyst comprises at least one transition metal selected from the group consisting of Cu, Pd, Ni, Pt, Rh, Ru, Os, Ag, Zn, Ir, Au and Co.

16. The method of claim 1, wherein no catalyst is used in Scheme 1.

17. The method of claim 1, wherein the product is provided in a yield of greater than 30%.

18. The method of claim 1, wherein the product is provided in a yield of greater than 40%.

19. The method of claim 1, wherein one of R¹ and R² is alkyl selected from the group consisting of methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, cyclopentyl, cyclohexyl, and combinations thereof.