Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-2018090691-A1
Application number	US-201715825798-A
Country	US
Kind code	A1
Filing date	Nov 29, 2017
Priority date	May 8, 2014
Publication date	Mar 29, 2018
Grant date	—

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

1 . 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 A1thorough A222 shown below;
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; and
wherein L is a substituted or unsubstituted cyclometallated ligand;
wherein R 1a is selected from the group consisting of:

wherein R 1b is selected from the group consisting of:

wherein R 1c is selected from the group consisting of:

wherein R 1d is selected from the group consisting of:

wherein R 1e is selected from the group consisting of:

wherein R 1f is selected from the group consisting of:

wherein which R 1g =H;
wherein the structures A1through A222 are:

2 . The compound of claim 1 , wherein the ligand L A is one of the ligands defined by L Ai designated using the formula A Z -R 1aj —R 1bk —R 1cl —R 1dm —R 1en —R 1fo —R 1g ;
wherein Z is an integer from 1 to 222 whereby A Z represents A1through A222;
wherein j is an integer from 1 to 6; and k, l, m, n and o are integers from 1 to 5;
wherein i=222((6((5((5((5((5(o−1)+n)−1)+m)−1)+l)−1)+k)−1)+j)−1)+Z.

3 . The compound of claim 1 , wherein the compound has a triplet excited state and wherein the linking group A 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 . (canceled)

6 . (canceled)

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

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 selected from the group consisting of Ir and Pt.

10 . The compound 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 X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO 2 , CR′R″, SiR′R″, and GeR′R″;
wherein R′ and R″ are optionally fused or joined to form a ring;
wherein each R a , R b , R c , and R d may represent from mono substitution to the possible maximum number of substitution, or no substitution;
wherein R′, R″, R a , R b , R c , 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 c , and R d are optionally fused or joined to form a ring or form a multidentate ligand.

11 .- 12 . (canceled)

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

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

Assignees

• Universal Display Corp

Inventors

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

Classifications

• C07D471/16

  Peri-condensed systems · CPC title

• C07F7/1804

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title

• C07F15/0086

  Platinum compounds · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title