Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-10263198-B2
Application number	US-201615291381-A
Country	US
Kind code	B2
Filing date	Oct 12, 2016
Priority date	May 8, 2014
Publication date	Apr 16, 2019
Grant date	Apr 16, 2019

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 organic light emitting devices, particularly as emissive dopants, 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. A compound having Formula (1):

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 having two to three linking atoms, wherein the linking atoms are each independently selected from the group consisting of C, Si, O, S, N, B or combinations thereof,
wherein the linking group A is independently selected from the group consisting of CR′R″—CR′R″—, —CR′R′—CR″R″—, —CH 2 —CH 2 —, —CR′R′—CR′R′—CR′R′—, —CR′R″—NR′—, —CR′═CR′—CR′R′—, —O—SiR′R′—, —CR′R″—S—, —CR′R″—O—, and —CR′R″—SiR′R′—,
wherein each R′ is independently selected from the group consisting of H, alkyl having 1 to 6 carbon atoms, phenyl and substituted phenyl,
wherein each R″ is independently selected from the group consisting of alkyl having 1 to 6 carbon atoms, phenyl and substituted phenyl,
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, and
wherein R 1a -R 1g are independently selected from hydrogen, alkyl, alkenyl, alkynyl, aralkyl, CN, CF 3 , CO 2 R, C(O)R, C(O)NR 2 , NR 2 , NO 2 , OR, SR, SO 2 , SOR, SO 3 R, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group, each R is independently selected from H, halo, alkyl, alkenyl, alkynyl, heteroalkyl, aralkyl, aryl, and heteroaryl; 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; and
L is a substituted or unsubstituted cyclometallated ligand.

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

3. The compound of claim 1 , wherein the compound has a triplet excited state and wherein the linking group stabilizes the bond between N 2 and C 1b from cleavage when the compound is in the triplet excited state.

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

5. The compound of claim 1 , wherein the compound has a peak emissive wavelength less than 480 nm.

6. The compound of claim 1 , wherein the compound has a peak emissive wavelength ranging from 400 nm to 500 nm.

7. The compound of claim 1 , wherein the linking group A is selected from the group consisting of —CH 2 —CH 2 —, —CH 2 —CH 2 —CH 2 —, —CHR″—CHR″—, —CH 2 —CR″R″, —CR″R″—CR″R″—, —CH 2 —CH 2 —CH 2 —, —CH 2 —S—, —S—CH 2 —, —O—SiR′R′—, and —SiR′R″—O.

8. The compound of claim 1 , wherein the metal is selected from the group consisting of Re, Ru, Os, Rh, Ir, Pd, Pt, and Au.

9. The compound of claim 1 , wherein the metal is Ir and n is 2 or 3; m is 0 or 1; and m+n is 3.

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

11. A device comprising a first organic light emitting device, further comprising:
an anode;
a cathode;
an organic layer, disposed between the anode and the cathode, comprising the compound of claim 1 .

12. A compound having Formula (2):

wherein M is Pt;
wherein A 1 and A 2 are each a first linking group having two to three linking atoms, wherein the linking atoms are each independently selected from the group consisting of C, Si, O, S, N, B or combinations thereof,
wherein the linking group A is independently selected from the group consisting of —CR′R″—CR′R″—, —CR′R′—CR″R″—, —CH 2 —CH 2 —, —CR′R′—CR′R′—CR′R′—, —CR′R″—NR′—, —CR′═CR′—CR′R′—, —O—SiR′R′—, —CR′R″—S—, —CR′R″—O—, and —CR′R″—SiR′R′—,
wherein each R′ is independently selected from the group consisting of H, alkyl having 1 to 6 carbon atoms, phenyl and substituted phenyl,
wherein each R″ is independently selected from the group consisting of alkyl having 1 to 6 carbon atoms, phenyl and substituted phenyl,

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, and
wherein R 1b -R 1f and R 2b -R 2f are independently selected from hydrogen, alkyl, alkenyl, alkynyl, aralkyl, CN, CF 3 , CO 2 R, C(O)R, C(O)NR 2 , NR 2 , NO 2 , OR, SR, SO 2 , SOR, SO 3 R, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group, wherein each R is independently selected from H, halo, alkyl, alkenyl, alkynyl, heteroalkyl, aralkyl, aryl, and heteroaryl;
any one of the ring atoms to which R 1b -R 1f and R 2b -R 2f 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; and
wherein R ab and R ac and/or R ga and R gb may bond to form a second linking group having one to three linking atoms each independently selected from the group consisting of B, N, P, O, S, Se, C, Si, Ge or combinations thereof.

13. The compound of claim 12 , wherein each of the first linking groups A 1 and A 2 is independently selected from the group consisting of —CR′R″—CR′R″—, —CR′R′—CR″R″—, and —CH 2 —CH 2 —.

14. The compound of claim 12 , wherein the compound has a triplet excited state and wherein the linking group stabilizes the bond between N 2 and C 1b from cleavage when the compound is in the triplet excited state.

15. The compound of claim 12 , wherein the compound has a peak emissive wavelength less than 500 nm.

16. The compound of claim 12 , wherein the compound has a peak emissive wavelength less than 480 nm.

17. The compound of claim 12 , wherein the compound has a peak emissive wavelength ranging from 400 nm to 500 nm.

18. The compound of claim 12 , wherein each first linking group A 1 and A 2 is independently selec

Assignees

• Universal Display Corp

Inventors

• Brooks Jason
• Szigethy Geza
• Morello Glenn
• Deng Jun
• Djurovich Peter I

Classifications

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title

• C07D498/16

  Peri-condensed systems · CPC title

• C07D513/16

  Peri-condensed systems · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• C07D231/54

  condensed with carbocyclic rings or ring systems · CPC title