Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-11495754-B2
Application number	US-202016775578-A
Country	US
Kind code	B2
Filing date	Jan 29, 2020
Priority date	May 8, 2014
Publication date	Nov 8, 2022
Grant date	Nov 8, 2022

Abstract

Imidazophenanthridine ligands and metal complexes are provided. The compounds exhibit improved stability through a linking substitution that links a nitrogen bonded carbon of an imidizole ring to a carbon on the adjacent fused aryl ring. The compounds may be used in OLEDs, particularly as emissive dopants in the emissive region in the OLEDs, providing devices with improved efficiency, stability, and manufacturing. In particular, the compounds provided herein may be used in blue devices having high efficiency.

First claim

We claim:

1. 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 a structure (L A ) n ML m according to Formula 1:

wherein M is a meta having an atomic weight greater than 40, n as a value of at least 1 and m+n is the maximum number of ligands that may be attached to the metal;
wherein A is a linking group selected from the group consisting of —CR′R″—CR′R″—, —CR′R′—CR″R″—, and —CR′R′—CR′R′—CR′R′—;
wherein each R′ is independently selected from the group consisting of H, D, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof,
wherein each R″ is independently selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, partially or fully deuterated variants thereof, and combinations thereof,
wherein R′s and R″s are optionally connected to form a saturated five membered ring or a saturated six membered ring, and combinations thereof,
wherein R 1a to R 1g are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof;
wherein any one of the ring atoms to which R 1b to R 1g are attached may be replaced with a nitrogen atom, wherein when the ring atom is replaced with a nitrogen atom the corresponding R group is not present;
wherein L is a substituted or unsubstituted cyclometallated ligand,
wherein L can be joined to R 1g through a linking group L 2 ;
wherein L 2 is selected from the group consisting of a single bond, NR, O, S, CR 1 R 2 , and SiR 1 R 2 ;
wherein R, R 1 , and R 2 can be same or different, and are independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof; wherein any adjacent R 1 and R 2 are optionally connected to form a saturated five membered ring or a saturated six membered ring.

2. The OLED of claim 1 , wherein A is selected from the group consisting of —CR′R″—CR′R″— and —CR′R′—CR″R″—.

3. The OLED of claim 2 , wherein each of R′ and R″ is independently selected from the group consisting of undeuterated alkyl, partially deuterated alkyl, and fully deuterated alkyl.

4. The OLED of claim 1 , wherein the compound has a peak emissive wavelength less than 500 nm.

5. The OLED of claim 1 , wherein the linking group is selected from the group consisting of:

6. The OLED of claim 1 , wherein at least one of R 1a to R 1g is selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, partially or fully deuterated variants thereof, and combinations thereof.

7. The OLED of claim 6 , wherein at least one of R 1b , R 1d and R 1c is selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, partially or fully deuterated variants thereof, and combinations thereof.

8. The OLED of claim 6 , wherein R 1d is selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, partially or fully deuterated variants thereof, and combinations thereof.

9. The OLED of claim 6 , wherein Ria is selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, partially or fully deuterated variants thereof, and combinations thereof.

10. The OLED of claim 8 , wherein R 1d is selected from the group consisting of non-deuterated alkyl, partially deuterated alkyl, and fully deuterated alkyl.

11. The OLED of claim 9 , wherein R 1a is selected from the group consisting of non-deuterated aryl, partially deuterated aryl, and fully deuterated aryl.

12. The OLED of claim 10 , wherein R 1d is selected from the group consisting of —CH 3 , —CD 3 , and isopropyl.

13. The OLED of claim 7 , wherein R 1f is selected from the group consisting of —CH 3 , —CD 3 , and isopropyl.

14. The OLED of claim 1 , wherein the metal is Jr.

15. The OLED of claim 1 , wherein the ligand L is selected from the group consisting of:

wherein each X 1 to X 13 are independently selected from the group consisting of carbon and nitrogen;
wherein each R a , R b , R e , and R d may represent from mono substitution to the possible maximum number of substitution, or no substitution;
wherein R a , R b , R e , and R d are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein any two adjacent substituents of R a , R b , R e , and R d are optionally fused or joined to form a ring or form a multidentate ligand.

16. The OLED of claim 1 , wherein ligand L is selected from the group consisting of.

17. The OLED of claim 15 , wherein the compound has a structure selected from the group consisting of (L A ) 3 Ir, (L A )Ir(L) 2 or (L A ) 2 Ir(L).

18. A consumer product comprising an organic light-emitting device comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having a structure (L A ) n ML m according to Formula 1:

wherein M is a metal having an atomic weight greater than 40, n has a value of at least 1 and m+n is the maximum number of ligands that may be attached to the metal;
wherein A is a linking group selected from the group consisting of —CR′R″—CR′R″—, —CR′R′—CR″R″—, and —CR′R′—CR′R′—CR′R′—;
wherein each R′ is independently selected from the group consisting of H, D, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof,
wherein each R″ is independently selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, partially or fully deuterated variants thereof, and combinations thereof,
wherein R′s and R″s are optionally connected to form a saturated five membered ring or a saturated six membered ring, and combinations thereof,
wherein R 1a to R 1g are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof;
wherein any one of the ring atoms to which R 1b to R 1g are attached may be replaced with a nitrogen atom, wherein when the ring atom is replaced with a nitrogen atom the corresponding R group is not present;
wherein L is a substituted or unsubstituted cyclometallated ligand,
wherein L can be joined to R 1g through a linking group L 2 ;
wherein L 2 is selected from the group consisting of a single bond, NR, O, S, CR 1 R 2 , and SiR 1 R 2 ;
wherein R, R 1 , and R 2 can be same or different, and are independently selected from the group consisting of hydroge

Assignees

• Universal Display Corp

Inventors

• Brooks Jason
• Szigethy Geza
• Morello Glenn
• Deng Jun
• Djurovich Peter I
• Chen Hsiao-Fan

Classifications

• H01L51/0087

  Electricity · mapped topic

• H01L51/5056

  Electricity · mapped topic

• H01L2251/5353

  Electricity · mapped topic

• H01L51/5072

  Electricity · mapped topic

• H01L51/5221

  Electricity · mapped topic