Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-11024811-B2
Application number	US-201916380057-A
Country	US
Kind code	B2
Filing date	Apr 10, 2019
Priority date	Jul 9, 2014
Publication date	Jun 1, 2021
Grant date	Jun 1, 2021

Abstract

A composition of materials including a first compound having a structure according to Formula I

First claim

We claim:

1. A composition of materials comprising a first compound, wherein the first compound has a formula:

wherein X is selected from the group consisting of O, S, and Se;
wherein L 1 is selected from the group consisting of phenyl, biphenyl, terphenyl, pyridine, pyrimidine, and combinations thereof;
wherein L 2 and L 3 are each independently selected from the group consisting of a direct bond, phenyl, biphenyl, terphenyl, pyridine, pyrimidine, and combinations thereof;
wherein G 4 is selected from the group consisting of phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, pyridine, pyrimidine, pyrazine, quinoline, isoquinoline, phenanthroline, and combinations thereof;
wherein G 2 , G 3 , and G 5 are each independently selected from the group consisting of phenyl, biphenyl, terphenyl, fluorene, naphthalene, phenanthrene, pyridine, pyrimidine, pyrazine, quinoline, isoquinoline, phenanthroline, aza-fluorene, and combinations thereof; and
wherein G 2 , G 3 , G 4 , and G 5 are each optionally further substituted with one or more unfused substituents selected from the group consisting of deuterium, alkyl, alkoxyl, cycloalkyl, cycloalkoxyl, halogen, nitro, nitrile, silyl, phenyl, biphenyl, terphenyl, pyridine, and combinations thereof.

2. The composition of claim 1 , wherein G 4 has the structure selected from the group consisting of:

3. The composition of claim 1 , wherein L 1 is selected from the group consisting of:

4. The composition of claim 1 , wherein G 2 , G 3 and G 5 are independently selected from the group consisting of:

wherein R B1 and R B2 are independently selected from a group consisting of hydrogen, deuterium, alkyl, cycloalkyl, alkoxyl, aryl, heteraryl, halogen, and combinations thereof; and
wherein R B1 and R B2 are optionally joined to form a ring.

5. The composition of claim 1 , wherein at least one of G 2 , G 3 , G 4 and G 5 is substituted with at least one fluorine atom.

6. The composition of claim 1 , wherein the first compound is selected from the group consisting of:

7. The composition of claim 1 , wherein the composition comprises a second compound;
wherein the second compound has the formula II:

wherein Ar 1 is selected from the group consisting of triphenylene, and aza-triphenylene;
wherein Ar 2 is selected from the group consisting of a direct bond, phenyl, biphenyl, terphenyl, naphthalene, pyridine, dibenzofuran, dibenzothiophene, dibenzoselenophene, aza-dibenzofuran, aza-dibenzothiophene, aza-dibenzoselenophene, and combinations thereof;
wherein Ar 3 is selected from the group consisting of benzene, biphenyl, terphenyl, naphthalene, pyridine, dibenzofuran, dibenzothiophene, dibenzoselenophene, aza-dibenzofuran, aza-dibenzothiophene, aza-dibenzoselenophene, carbazole, aza-carbazole, and combinations thereof; and
wherein Ar 1 , Ar 2 and Ar 3 are each, independently, optionally further substituted with one or more substitutions selected from the group consisting of deuterium, halogen, alkyl, aryl, heteroaryl, and combinations thereof.

8. The composition of claim 7 , wherein the second compound is selected from the group consisting of

wherein X is selected from the group consisting of O, S and Se;
wherein R 1 and R 4 each independently represents mono, di, or tri, substitution, or no substitution;
wherein R 2 , R 3 , R 5 , and R 6 each independently represents mono, di, tri, or tetra substitution, or no substitution; and
wherein R 1 to R 6 are each independently selected from the group consisting of hydrogen, deuterium, benzene, biphenyl, terphenyl, naphthalene, fluorene, triphenylene, phenanthrene, dibenzofuran, dibenzothiophene, carbazole and combinations thereof.

9. The composition of claim 7 , wherein the second compound is selected from the group consisting of

10. A composition comprising a mixture of a first compound and a second compound selected from the group consisting of:

11. The composition of claim 1 , wherein the composition comprises a second compound; wherein the second compound is a phosphorescent emissive Ir complex having at least one substituent selected from the group consisting of alkyl, cycloalkyl, partially or fully deuterated variants thereof, partially or fully fluorinated variants thereof, and combinations thereof.

12. A first device comprising a first organic light emitting device, the first organic light emitting device comprising:
an anode;
a cathode; and

an organic layer, disposed between the anode and the cathode, comprising A composition of materials comprising a first compound, wherein the first compound has a formula:

wherein X is selected from the group consisting of O, S, and Se;
wherein L 1 is selected from the group consisting of phenyl, biphenyl, terphenyl, pyridine, pyrimidine, and combinations thereof;
wherein L 2 and L 3 are each independently selected from the group consisting of a direct bond, phenyl, biphenyl, terphenyl, pyridine, pyrimidine, and combinations thereof;
wherein G 4 is selected from the group consisting of phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, pyridine, pyrimidine, pyrazine, quinoline, isoquinoline, phenanthroline, and combinations thereof;
wherein G 2 , G 3 , and G 5 are each independently selected from the group consisting of phenyl, biphenyl, terphenyl, fluorene, naphthalene, phenanthrene, pyridine, pyrimidine, pyrazine, quinoline, isoquinoline, phenanthroline, aza-fluorene, and combinations thereof; and
wherein G 2 , G 3 , G 4 , and G 5 are each optionally further substituted

Assignees

• Universal Display Corp

Inventors

• Zeng Lichang
• Layek Suman
• Boudreault Pierre-Luc T
• Elshenawy Zeinab
• Kottas Gregg
• Dyatkin Alexey Borisovich
• Joseph Scott
• Adamovich Vadim
• Xia Chuanjun
• Wang Ting-Chih
• Yeager Walter

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• C07D409/10 Primary

  linked by a carbon chain containing aromatic rings · CPC title

• H10K85/624

  containing six or more rings · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• C07D421/14

  containing three or more hetero rings · CPC title