Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-10566547-B2
Application number	US-201715622356-A
Country	US
Kind code	B2
Filing date	Jun 14, 2017
Priority date	Jul 11, 2016
Publication date	Feb 18, 2020
Grant date	Feb 18, 2020

Abstract

The present application includes novel compounds containing xanthene and spiro dixanthene ring structures. These compounds are useful as host materials with high triplet energies for phosphorescent electroluminescent devices.

First claim

We claim:

1. A compound having Formula I:

wherein X is selected from the group consisting of O, S, Se;
wherein Y is C or Si;
wherein L 1 is selected from the group consisting of a direct bond, alkyl, ether, alkoxyl, cycloalkyl, cycloalkoxyl, silyl, benzene, pyridine, pyrimidine, pyrazine, pyrrole, oxadiazole, thiadiazole, selenadiazole, and combinations thereof;
wherein L 2 is selected from the group consisting of a direct bond, alkyl, ether, alkoxyl, cycloalkyl, cycloalkoxyl, silyl, benzene, pyridine, pyrimidine, pyrazine, oxadiazole, thiadiazole, selenadiazole, and combinations thereof;
wherein G 1 is selected from the group consisting of fluorene, dibenzofuran, dibenzoselenophene, triphenylene, tetraphenylene, azafluorene, azacarbazole, azadibenzofuran, azadibenzothiophene, azadibenzoselenophene, azatriphenylene, azatetraphenylene, and combinations thereof;
wherein G 2 is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, ether, alkoxyl, cycloalkyl, cycloalkoxyl, silyl, aryl, and combinations thereof;
wherein R 1 and R 2 each independently represents none to the maximum available number of substituents;
wherein R 1 and R 2 are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, ether, alkoxyl, cycloalkyl, cycloalkoxyl, silyl, and combinations thereof;
wherein G 1 , R 1 and R 2 are each independently and optionally further substituted with hydrogen, deuterium, halogen, alkyl, ether, alkoxyl, cycloalkyl, cycloalkoxyl, silyl, amine, aryl, heteroaryl and combinations thereof;
wherein G 2 is optionally further substituted with hydrogen, deuterium, halogen, alkyl, ether, alkoxyl, cycloalkyl, cycloalkoxyl, silyl, amine, aryl, and combinations thereof;
wherein G 1 -L 1 is different from G 2 -L 2 and there is no bond between G 1 -L 1 and G 2 -L 2 ; and
wherein the lowest triplet excited state energy of the compound is greater than 2.9 eV.

2. The compound of claim 1 , wherein at least one of L 1 and L 2 is a direct bond.

3. The compound of claim 1 , wherein L 1 and L 2 are each a direct bond.

4. The compound of claim 1 , wherein L 1 is a silyl group.

5. The compound of claim 1 , wherein G 1 is selected from the group consisting of:

wherein Z 1 is selected from the group consisting of O, S and Se;
wherein R 4 and R 5 are each independently selected from the group consisting of alkyl, alkoxyl, cycloalkyl, cycloalkoxyl, silyl, benzene, and combinations thereof;
wherein R 4 and R 5 are optionally joined to form a ring; and
wherein G 1 can be further substituted.

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

wherein L 2 is selected from the group consisting of:

wherein each occurrence of Z 1 is independently selected from the group consisting of O, S and Se;
wherein R 4 to R 7 are each independently selected from the group consisting of alkyl, alkoxyl, cycloalkyl, cycloalkoxyl, silyl, benzene, and combinations thereof;
wherein R 4 and R 5 are optionally joined to form a ring; and
wherein L 1 and L 2 can each be further substituted.

7. The compound of claim 1 , wherein the compound is selected from the group consisting of:

8. An organic light emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having Formula I:

wherein X is selected from the group consisting of O, S, Se;
wherein Y is C or Si;
wherein L 1 is selected from the group consisting of a direct bond, alkyl, ether, alkoxyl, cycloalkyl, cycloalkoxyl, silyl, benzene, pyridine, pyrimidine, pyrazine, pyrrole, oxadiazole, thiadiazole, selenadiazole, and combinations thereof;
wherein L 2 is selected from the group consisting of a direct bond, alkyl, ether, alkoxyl, cycloalkyl, cycloalkoxyl, silyl, benzene, pyridine, pyrimidine, pyrazine, oxadiazole, thiadiazole, selenadiazole, and combinations thereof;
wherein G 1 is selected from the group consisting of fluorene, dibenzofuran, dibenzoselenophene, triphenylene, tetraphenylene, azafluorene, azacarbazole, azadibenzofuran, azadibenzothiophene, azadibenzoselenophene, azatriphenylene, azatetraphenylene, and combinations thereof;
wherein G 2 is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, ether, alkoxyl, cycloalkyl, cycloalkoxyl, silyl, aryl, and combinations thereof;
wherein R 1 and R 2 each independently represents none to the maximum available number of substituents;
wherein R 1 and R 2 are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, ether, alkoxyl, cycloalkyl, cycloalkoxyl, silyl, and combinations thereof;
wherein G 1 , R 1 and R 2 are each independently and optionally further substituted with hydrogen, deuterium, halogen, alkyl, ether, alkoxyl, cycloalkyl, cycloalkoxyl, silyl, amine, aryl, heteroaryl and combinations thereof;
wherein G 2 is optionally further substituted with hydrogen, deuterium, halogen, alkyl, ether, alkoxyl, cycloalkyl, cycloalkoxyl, silyl, amine, aryl, and combinations thereof;
wherein G 1 -L 1 is different from G 2 -L 2 and there is no bond between G 1 -L 1 and G 2 -L 2 ; and
wherein the lowest triplet excited state energy of the compound is greater than 2.9 eV.

9. The OLED of claim 8 , wherein the organic layer is an emissive layer and the compound of Formula I is a host.

10. The OLED of claim 8 , wherein the organic layer further comprises a phosphorescent emissive dopant; wherein the emissive dopant is a transition metal complex having at least one ligand or part of the

Assignees

• Universal Display Corp

Inventors

• Zeng Lichang
• Wolohan Peter
• Fitzgerald George
• Silverstein Daniel W

Classifications

• C07D311/82

  Xanthenes · CPC title

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C07D405/10

  linked by a carbon chain containing aromatic rings · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title