IP Library › Granted Patent US 12,497,420
Granted Patent B2
US 12,497,420 · App. 17/477,809 · Granted Dec 16, 2025

Organic electroluminescent materials and devices

Inventors: Morgan C. Macinnis (Yardley, PA); Hsiao-Fan Chen (Lawrence Township, NJ); Noah Horwitz (Ewing, NJ); Nicholas J. Thompson (New Hope, PA)
Assignee: UNIVERSAL DISPLAY CORPORATION
C07F15/0086H10K85/346H10K85/40H10K85/622H10K85/624H10K85/626H10K85/633H10K85/654H10K85/6572H10K85/6574H10K85/6576H10K50/11H10K2101/10H10K2101/30H10K2101/40
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,497,420
App. No.
17/477,809
Granted
Dec 16, 2025
Kind
B2
Abstract

Provided are organometallic compounds including a ligand L A of Also provided are formulations including these organometallic compounds. Further provided are OLEDs and related consumer products that utilize these organometallic compounds.

Claims (144)

1 . A compound comprising a ligand L A of

wherein:

ring A is independently a monocyclic 7-membered to 10-membered heterocyclic ring;

X 1 -X 6 are each independently C or N;

K 3 is a direct bond, O, or S;

R A , R B , and R C each independently represents zero, mono, or up to the maximum allowed number of substitutions to its associated ring; and

each of R 1 , R A , R B , and R C is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof,

wherein:

the ligand L A is complexed to a metal M through the two indicated dashed lines;

M is Ru, Os, Ir, Pd, Pt, Cu, Ag, or Au, and can be coordinated to other ligands;

the ligand L A can be joined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand;

any two adjacent R A , R B , R C , or R 1 can be joined or fused to form a ring, and at least one pair of adjacent R A is joined to form an aryl or heteroaryl ring fused to Ring A.

2 . The compound of claim 1 , wherein, other than the pair of adjacent R A that are joined, each of R 1 , R A , R B , and R C is independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

3 . The compound of claim 1 , wherein X 1 -X 3 are each C, or X 4 -X 6 are each C, or X 1 -X 6 are each C.

4 . The compound of claim 1 , wherein four adjacent R A substituents are joined to form two fused rings to ring A.

5 . The compound of claim 1 , wherein ring A is an 8-membered, 9-membered, or 10-membered ring and 6 adjacent R A substituents are joined to form three separate rings all fused to ring A.

6 . The compound of claim 1 , wherein the compound has a structure of

wherein:

M 1 is Pd or Pt;

moieties C and D are each independently a monocyclic or polycyclic ring structure comprising 5-membered and/or 6-membered carbocyclic or heterocyclic rings;

Z 1 and Z 2 are each independently C or N;

K 1 , K 2 , and K 3 are each independently selected from the group consisting of a direct bond, O, and S, wherein at least two of K 1 , K 2 , or K 3 are direct bonds;

L 1 , L 2 , and L 3 are each independently selected from the group consisting of a direct bond, BR, BRR, NR, PR, O, S, Se, C—O, S—O, SO 2 , CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, and combinations thereof, wherein at least one of L 1 or L 2 is present;

n1, n2, and n3 each are 0 or 1 with n1+n2+n3=2 or 3;

X 1 -X 9 are each independently C or N;

R C and R D each independently represent zero, mono, or up to the maximum allowed number of substitutions to its associated ring;

each of R C , and R D is independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof; and

in addition to the pair of adjacent R A that are joined, any two adjacent R A , R B , R C , R D , or R 1 can be joined or fused together to form a ring where chemically feasible.

7 . The compound of claim 6 , wherein moiety C and moiety D are both 6-membered aromatic rings, or moiety C is a 5-membered or 6-membered heteroaromatic ring.

8 . The compound of claim 6 , wherein L′ is O, SiRR′, or CRR′.

9 . The compound of claim 6 , wherein Z 2 is N and Z 1 is C, or Z 2 is C and Z 1 is N.

10 . The compound of claim 6 , wherein L 2 is a direct bond, or NR.

11 . The compound of claim 6 , wherein K 1 , K 2 , and K 3 are each direct bonds, or one of K 1 , K 2 , or K 3 is O.

12 . The compound of claim 6 , wherein the compound has a structure of:

wherein Z 3 is C or N; and

in addition to the pair of adjacent R A that are joined, any two adjacent R A , R B , R C , R D , or R 1 can be joined or fused together to form a ring.

13 . The compound of claim 12 , wherein the compound is selected from the group consisting of:

wherein:

R E and R F each independently represent zero, mono, or up to the maximum allowed number of substitutions to its associated ring; and

each R E , R F , R X , and R Y is independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

14 . The compound of claim 6 , wherein the compound has a structure of

wherein L A′ is selected from the group consisting of: L A′ 3-(Rs)(Rf)(Ru), L A′ 4-(Rs)(Rf)(Ru), L A′ 5-(Rs)(Rf)(Ru), and L A′ 9-(Rs)(Rf)(Ru), wherein s, t, and u are each independently an integer from 1 to 87, wherein:

Ligand L A ′

Structure of L A ′

L A ′3-(R1)(R1)(R1) to L A ′3-(R87)(R87)(R87) having the structure

L A ′4-(R1)(R1)(R1) to L A ′4- (R87)(R87)(R87) having the structure

L A ′5-(R1)(R1)(R1) to L A ′5-(R87)(R87)(R87) having the structure

L A ′9-(R1)(R1)(R1) to L A ′9-(R87)(R87)(R87) having the structure

wherein L A″ is selected from the group consisting of:

L A″ 1-(Rs)(Rf)(Ru), L A″ 2-(Rs)(Rf)(Ru), L A″ 3-(Rs)(Rt)(Ru), L A″ 4-(Rs)(Rf)(Ru), L A″ 5-(Rs)(Rt)(Ru), L A″ 6-(Rs)(Rf)(Ru), L A″ 7-(Rs)(Rt)(Ru), L A″ 14-(Rs)(Rt)(Ru), L A″ 16-(Rs)(Rt)(Ru), L A″ 17-(Rs)(Rf)(Ru), L A″ 18-(Rs)(Rt)(Ru), L A″ 19-(Rs)(Rt)(Ru), L A″ 20-(Rs)(Rf)(Ru), L A″ 21-(Rs)(Rf)(Ru), L A″ 22-(Rs)(Rf)(Ru), L A″ 23-(Rs)(Rf)(Ru), and L A″ 24-(Rs)(Rt)(Ru), wherein s, t, and u are each independently an integer from 1 to 87, wherein:

Ligand L A ″

Structure of L A ″

L A ″1- (R1)(R1)(R1) to L A ″1- (R87)(R87)(R87) having the structure

L A ″2- (R1)(R1)(R1) to L A ″2- (R87)(R87)(R87) having the structure

L A ″3- (R1)(R1)(R1) to L A ″3- (R87)(R87)(R87) having the structure

L A ″4- (R1)(R1)(R1) to L A ″4- (R87)(R87)(R87) having the structure

L A ″5- (R1)(R1)(R1) to L A ″5- (R87)(R87)(R87) having the structure

L A ″6- (R1)(R1)(R1) to L A ″6- (R87)(R87)(R87) having the structure

L A ″7- (R1)(R1)(R1) to L A ″7- (R87)(R87)(R87) having the structure

L A ″14- (R1)(R1)(R1) to L A ″14- (R87)(R87)(R87) having the structure

L A ″16- (R1)(R1)(R1) to L A ″16- (R87)(R87)(R87) having the structure

L A ″17- (R1)(R1)(R1) to L A ″17- (R87)(R87)(R87) having the structure

L A ″18- (R1)(R1)(R1) to L A ″18- (R87)(R87)(R87) having the structure

L A ″19- (R1)(R1)(R1) to L A ″19- (R87)(R87)(R87) having the structure

L A ″20- (R1)(R1)(R1) to L A ″20- (R87)(R87)(R87) having the structure

L A ″21- (R1)(R1)(R1) to L A ″21- (R87)(R87)(R87) having the structure

L A ″22- (R1)(R1)(R1) to L A ″22- (R87)(R87)(R87) having the structure

L A ″23- (R1)(R1)(R1) to L A ″23- (R87)(R87)(R87) having the structure

L A ″24- (R1)(R1)(R1) to L A ″24- (R87)(R87)(R87) having the structure

and

wherein L Y is selected from the group consisting of:

L Y 1-(Rs)(Rt)(Ru), L Y 2-(Rs)(Rf)(Ru), L Y 3-(Rs)(Rf)(Ru), L Y 4-(Rs)(Rf)(Ru), L Y 5-(Rs)(Rf)(Ru), L Y 6-(Rs)(Rt)(Ru), L Y 7-(Rs)(Rf)(Ru), L Y 8-(Rs)(Rf)(Ru), L Y 9-(Rs)(Rf)(Ru), L Y 10-(Rs)(Rf)(Ru), L Y 11-(Rs)(Rt)(Ru), L Y 12-(Rs)(Rt)(Ru), L Y 13-(Rs)(Rf)(Ru), L Y 14-(Rs)(Rf)(Ru), L Y 15-(Rs)(Rf)(Ru), L Y 16-(Rs)(Rf)(Ru), L Y 17-(Rs)(Rt)(Ru), L Y 18-(Rs)(Rf)(Ru), L Y 19-(Rs)(Rf)(Ru), L Y 20-(Rs)(Rf)(Ru), L Y 21-(Rs)(Rf)(Ru), L Y 22-(Rs)(Rf)(Ru), L Y 23-(Rs)(Rt)(Ru), L Y 24-(Rs)(Rf)(Ru), L Y 25-(Rs)(Rf)(Ru), L Y 26-(Rs)(Rf)(Ru), L Y 27-(Rs)(Rt)(Ru), L Y 28-(Rs)(Rf)(Ru), L Y 29-(Rs)(Rf)(Ru), L Y 30-(Rs)(Rt)(Ru), L Y 31-(Rs)(Rf)(Ru), L Y 32-(Rs)(Rt)(Ru), L Y 33-(Rs)(Rf)(Ru), wherein s, t, and u are each independently an integer from 1 to 87, wherein:

L Y

Structure of L Y

L Y 1-(R1)(R1)(R1) to L Y 1-(R87)(R87)(R87), having the structure

L Y 2-(R1)(R1)(R1) to L Y 2-(R87)(R87)(R87), having the structure

L Y 3-(R1)(R1)(R1) to L Y 3-(R87)(R87)(R87) having the structure

L Y 4-(1)(1)(1) to L Y 4- (87)(87)(87) having the structure

L Y 5-(R1)(R1)(R1) to L Y 5-(R87)(R87)(R87) having the structure

L Y 6-(R1)(R1)(R1) to L Y 6-(R87)(R87)(R87) having the structure

L Y 7-(R1)(R1)(R1) to L Y 7-(R87)(R87)(R87) having the structure

L Y 8-(R1)(R1)(R1) to L Y 8-(R87)(R87)(R87) having the structure

L Y 9-(R1)(R1)(R1) to L Y 9-(R87)(R87)(R87) having the structure

L Y 10-(R1)(R1)(R1) to L Y 10-(R87)(R87)(R87) having the structure

L Y 11-(R1)(R1)(R1) to L Y 11-(R87)(R87)(R87) having the structure

L Y 12-(R1)(R1)(R1) to L Y 12-(R87)(R87)(R87) having the structure

L Y 13-(R1)(R1)(R1) to L Y 13-(R87)(R87)(R87) having the structure

L Y 14-(R1)(R1)(R1) to L Y 14-(R87)(R87)(R87) having the structure

L Y 15-(R1)(R1)(R1) to L Y 15-(R87)(R87)(R87) having the structure

L Y 16-(R1)(R1)(R1) to L Y 16-(R87)(R87)(R87) having the structure

L Y 17-(R1)(R1)(R1) to L Y 17-(R87)(R87)(R87) having the structure

L Y 18-(R1)(R1)(R1) to L Y 18-(R87)(R87)(R87), having the structure

L Y 19-(R1)(R1)(R1) to L Y 19-(R87)(R87)(R87) having the structure

L Y 20-(R1)(R1)(R1) to L Y 20-(R87)(R87)(R87) having the structure

L Y 21-(R1)(R1)(R1) to L Y 21-(R87)(R87)(R87) having the structure

L Y 22-(R1)(R1)(R1) to L Y 22-(R87)(R87)(R87) having the structure

L Y 23-(R1)(R1)(R1) to L Y 23-(R87)(R87)(R87) having the structure

L Y 24-(R1)(R1)(R1) to L Y 24-(R87)(R87)(R87) having the structure

L Y 25-(R1)(R1)(R1) to L Y 25-(R87)(R87)(R87) having the structure

L Y 26-(R1)(R1)(R1) to L Y 26-(R87)(R87)(R87) having the structure

L Y 27-(R1)(R1)(R1) to L Y 27-(R87)(R87)(R87) having the structure

L Y 28-(R1)(R1)(R1) to L Y 28-(R87)(R87)(R87) having the structure

L Y 29-(R1)(R1)(R1) to L Y 29-(R87)(R87)(R87) having the structure

L Y 30-(R1)(R1)(R1) to L Y 30-(R87)(R87)(R87) having the structure

L Y 31-(R1)(R1)(R1) to L Y 31-(R87) R87)(R87) having the structure

L Y 32-(R1)(R1)(R1) to L Y 32-(R87)(R87)(R87) having the structure

L Y 33-(R1)(R1)(R1) to L Y 33-(R87)(R87)(R87) having the structure

wherein R 1 to R 87 have the following structures:

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

16 . An organic light emitting device (OLED) comprising:

an anode;

a cathode; and

an organic layer disposed between the anode and the cathode,

wherein the organic layer comprises a compound comprising a ligand L A of

wherein:

ring A is independently a monocyclic 7-membered to 10-membered heterocyclic ring;

X 1 -X 6 are each independently C or N;

K 3 is a direct bond, O, or S;

R A , R B , and R C each independently represents zero, mono, or up to the maximum allowed number of substitutions to its associated ring; and

each of R 1 , R A , R B , and R C is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof,

wherein:

the ligand L A is complexed to a metal M through the two indicated dashed lines;

M is Ru, Os, Ir, Pd, Pt, Cu, Ag, or Au, and can be coordinated to other ligands;

the ligand L A can be joined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand;

any two adjacent R A , R B , R C , or R 1 can be joined or fused to form a ring, and at least one pair of adjacent R A is joined to form an aryl or heteroaryl ring fused to Ring A.

17 . The OLED of claim 16 , wherein the organic layer further comprises a host, wherein host comprises at least one chemical moiety selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, and aza-(5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene).

18 . The OLED of claim 17 , wherein the host is selected from the group consisting of:

and combinations thereof.

19 . A consumer product comprising an organic light-emitting device (OLED) comprising:

an anode;

a cathode; and

an organic layer disposed between the anode and the cathode,

wherein the organic layer comprises a compound comprising a ligand L A of

wherein:

ring A is independently a monocyclic 7-membered to 10-membered heterocyclic ring;

X 1 -X 6 are each independently C or N;

K 3 is a direct bond, O, or S;

R A , R B , and R C each independently represents zero, mono, or up to the maximum allowed number of substitutions to its associated ring; and

each of R 1 , R A , R B , and R C is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof,

wherein:

the ligand L A is complexed to a metal M through the two indicated dashed lines;

M is Ru, Os, Ir, Pd, Pt, Cu, Ag, or Au, and can be coordinated to other ligands;

the ligand L A can be joined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand;

any two adjacent R A , R B , R C , or R 1 can be joined or fused to form a ring, and at least one pair of adjacent R A is are joined to form an aryl or heteroaryl ring fused to Ring A.

Assignments (1)
NUNC PRO TUNC ASSIGNMENT Recorded Sep 21, 2021
From: MACINNIS, MORGAN C.; CHEN, HSIAO-FAN; HORWITZ, NOAH; THOMPSON, NICHOLAS J.
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 057548/0767 →
Continuity (3)
Provisional Application 63193755 · May 27, 2021
Provisional Application 63087062 · Oct 2, 2020
Related Publication 20220112232A1 · Apr 14, 2022
References Cited (192)
US 4769292A · Tang et al. · 1988 [cited by applicant]
US 5061569A · VanSlyke et al. · 1991 [cited by applicant]
US 5247190A · Friend et al. · 1993 [cited by applicant]
US 5703436A · Forrest et al. · 1997 [cited by applicant]
US 5707745A · Forrest et al. · 1998 [cited by applicant]
US 5834893A · Bulovic et al. · 1998 [cited by applicant]
US 5844363A · Gu et al. · 1998 [cited by applicant]
US 6013982A · Thompson et al. · 2000 [cited by applicant]
US 6087196A · Sturm et al. · 2000 [cited by applicant]
US 6091195A · Forrest et al. · 2000 [cited by applicant]
US 6097147A · Baldo et al. · 2000 [cited by applicant]
US 6294398B1 · Kim et al. · 2001 [cited by applicant]
US 6303238B1 · Thompson et al. · 2001 [cited by applicant]
US 6337102B1 · Forrest et al. · 2002 [cited by applicant]
US 6468819B1 · Kim et al. · 2002 [cited by applicant]
US 6528187B1 · Okada · 2003 [cited by applicant]
US 6687266B1 · Ma et al. · 2004 [cited by applicant]
US 6835469B2 · Kwong et al. · 2004 [cited by applicant]
US 6921915B2 · Takiguchi et al. · 2005 [cited by applicant]
US 7087321B2 · Kwong et al. · 2006 [cited by applicant]
US 7090928B2 · Thompson et al. · 2006 [cited by applicant]
US 7154114B2 · Brooks et al. · 2006 [cited by applicant]
US 7250226B2 · Tokito et al. · 2007 [cited by applicant]
US 7279704B2 · Walters et al. · 2007 [cited by applicant]
US 7332232B2 · Ma et al. · 2008 [cited by applicant]
US 7338722B2 · Thompson et al. · 2008 [cited by applicant]
US 7393599B2 · Thompson et al. · 2008 [cited by applicant]
US 7396598B2 · Takeuchi et al. · 2008 [cited by applicant]
US 7431968B1 · Shtein et al. · 2008 [cited by applicant]
US 7445855B2 · Mackenzie et al. · 2008 [cited by applicant]
US 7534505B2 · Lin et al. · 2009 [cited by applicant]
US 20020034656A1 · Thompson et al. · 2002 [cited by applicant]
US 20020134984A1 · Igarashi · 2002 [cited by applicant]
US 20020158242A1 · Son et al. · 2002 [cited by applicant]
US 20030138657A1 · Li et al. · 2003 [cited by applicant]
US 20030152802A1 · Tsuboyama et al. · 2003 [cited by applicant]
US 20030162053A1 · Marks et al. · 2003 [cited by applicant]
US 20030175553A1 · Thompson et al. · 2003 [cited by applicant]
US 20030230980A1 · Forrest et al. · 2003 [cited by applicant]
US 20040036077A1 · Ise · 2004 [cited by applicant]
US 20040137267A1 · Igarashi et al. · 2004 [cited by applicant]
US 20040137268A1 · Igarashi et al. · 2004 [cited by applicant]
US 20040174116A1 · Lu et al. · 2004 [cited by applicant]
US 20050025993A1 · Thompson et al. · 2005 [cited by applicant]
US 20050112407A1 · Ogasawara et al. · 2005 [cited by applicant]
US 20050238919A1 · Ogasawara · 2005 [cited by applicant]
US 20050244673A1 · Satoh et al. · 2005 [cited by applicant]
US 20050260441A1 · Thompson et al. · 2005 [cited by applicant]
US 20050260449A1 · Walters et al. · 2005 [cited by applicant]
US 20060008670A1 · Lin et al. · 2006 [cited by applicant]
US 20060202194A1 · Jeong et al. · 2006 [cited by applicant]
US 20060240279A1 · Adamovich et al. · 2006 [cited by applicant]
US 20060251923A1 · Lin et al. · 2006 [cited by applicant]
US 20060263635A1 · Ise · 2006 [cited by applicant]
US 20060280965A1 · Kwong et al. · 2006 [cited by applicant]
US 20070190359A1 · Knowles et al. · 2007 [cited by applicant]
US 20070278938A1 · Yabunouchi et al. · 2007 [cited by applicant]
US 20080015355A1 · Schafer et al. · 2008 [cited by applicant]
US 20080018221A1 · Egen et al. · 2008 [cited by applicant]
US 20080106190A1 · Yabunouchi et al. · 2008 [cited by applicant]
US 20080124572A1 · Mizuki et al. · 2008 [cited by applicant]
US 20080220265A1 · Xia et al. · 2008 [cited by applicant]
US 20080233410A1 · Mashima · 2008 [cited by applicant]
US 20080297033A1 · Knowles et al. · 2008 [cited by applicant]
US 20090008605A1 · Kawamura et al. · 2009 [cited by applicant]
US 20090009065A1 · Nishimura et al. · 2009 [cited by applicant]
US 20090017330A1 · Iwakuma et al. · 2009 [cited by applicant]
US 20090030202A1 · Iwakuma et al. · 2009 [cited by applicant]
US 20090039776A1 · Yamada et al. · 2009 [cited by applicant]
US 20090045730A1 · Nishimura et al. · 2009 [cited by applicant]
US 20090045731A1 · Nishimura et al. · 2009 [cited by applicant]
US 20090101870A1 · Prakash et al. · 2009 [cited by applicant]
US 20090108737A1 · Kwong et al. · 2009 [cited by applicant]
US 20090115316A1 · Zheng et al. · 2009 [cited by applicant]
US 20090165846A1 · Johannes et al. · 2009 [cited by applicant]
US 20090167162A1 · Lin et al. · 2009 [cited by applicant]
US 20090179554A1 · Kuma et al. · 2009 [cited by applicant]
US 20100237334A1 · Ma · 2010 [cited by examiner]
US 20150105556A1 · Li · 2015 [cited by examiner]
US 20150129840A1 · Tsai · 2015 [cited by applicant]
US 20150171350A1 · Strassner · 2015 [cited by applicant]
US 20190280222A1 · Kim et al. · 2019 [cited by applicant]
US 20230065887A1 · Chen · 2023 [cited by examiner]
US 20230115552A1 · Thompson · 2023 [cited by examiner]
US 20230159578A1 · Chen · 2023 [cited by examiner]
US 20230167145A1 · Thompson · 2023 [cited by examiner]
US 20230250120A1 · Hamze · 2023 [cited by examiner]
US 20240083929A1 · Thompson · 2024 [cited by examiner]
US 20240090314A1 · Wang · 2024 [cited by examiner]
US 20240122059A1 · Chen · 2024 [cited by examiner]
US 20240251656A1 · Chen · 2024 [cited by examiner]
CN 115448932 · 2022 [cited by applicant]
EP 0650955 · 1995 [cited by applicant]
EP 1725079 · 2006 [cited by applicant]
EP 2034538 · 2009 [cited by applicant]
JP 200511610 · 2005 [cited by applicant]
JP 2007123392 · 2007 [cited by applicant]
JP 2007254297 · 2007 [cited by applicant]
JP 2008074939 · 2008 [cited by applicant]
JP 2014170820 · 2014 [cited by applicant]
WO 0139234 · 2001 [cited by applicant]
WO 0202714 · 2002 [cited by applicant]
WO 02015654 · 2002 [cited by applicant]
WO 03040257 · 2003 [cited by applicant]
WO 03060956 · 2003 [cited by applicant]
WO 2004093207 · 2004 [cited by applicant]
WO 2004107822 · 2004 [cited by applicant]
WO 2005014551 · 2005 [cited by applicant]
WO 2005019373 · 2005 [cited by applicant]
WO 2005030900 · 2005 [cited by applicant]
WO 2005089025 · 2005 [cited by applicant]
WO 2005123873 · 2005 [cited by applicant]
WO 2006009024 · 2006 [cited by applicant]
WO 2006056418 · 2006 [cited by applicant]
WO 2006072002 · 2006 [cited by applicant]
WO 2006082742 · 2006 [cited by applicant]
WO 2006098120 · 2006 [cited by applicant]
WO 2006100298 · 2006 [cited by applicant]
WO 2006103874 · 2006 [cited by applicant]
WO 2006114966 · 2006 [cited by applicant]
WO 2006132173 · 2006 [cited by applicant]
WO 2007002683 · 2007 [cited by applicant]
WO 2007004380 · 2007 [cited by applicant]
WO 2007058255 · 2007 [cited by applicant]
WO 2007063754 · 2007 [cited by applicant]
WO 2007063796 · 2007 [cited by applicant]
WO 2008056746 · 2008 [cited by applicant]
WO 2008101842 · 2008 [cited by applicant]
WO 2008132085 · 2008 [cited by applicant]
WO 2009000673 · 2008 [cited by applicant]
WO 2009003898 · 2009 [cited by applicant]
WO 2009008311 · 2009 [cited by applicant]
WO 2009018009 · 2009 [cited by applicant]
WO 2009021126 · 2009 [cited by applicant]
WO 2009050290 · 2009 [cited by applicant]
WO 2009062578 · 2009 [cited by applicant]
WO 2009063833 · 2009 [cited by applicant]
WO 2009066778 · 2009 [cited by applicant]
WO 2009066779 · 2009 [cited by applicant]
WO 2009086028 · 2009 [cited by applicant]
WO 2009100991 · 2009 [cited by applicant]
Adachi, Chihaya et al., “Organic Electroluminescent Device Having a Hole Conductor as an Emitting Layer,” Appl. Phys. Lett., 55(15): 1489-1491 (1989). [cited by applicant]
Adachi, Chihaya et al., “Nearly 100% Internal Phosphorescence Efficiency in an Organic Light Emitting Device,” J. Appl. Phys., 90(10): 5048-5051 (2001). [cited by applicant]
Adachi, Chihaya et al., “High-Efficiency Red Electrophosphorescence Devices,” Appl. Phys. Lett., 78(11)1622-1624 (2001). [cited by applicant]
Aonuma, Masaki et al., “Material Design of Hole Transport Materials Capable of Thick-Film Formation in Organic Light Emitting Diodes,” Appl. Phys. Lett., 90, Apr. 30, 2007, 183503-1-183503-3. [cited by applicant]
Baldo et al., Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices, Nature, vol. 395, 151-154, (1998). [cited by applicant]
Baldo et al., Very high-efficiency green organic light-emitting devices based on electrophosphorescence, Appl. Phys. Lett., vol. 75, No. 1, 4-6 (1999). [cited by applicant]
Gao, Zhiqiang et al., “Bright-Blue Electroluminescence From a Silyl-Substituted ter-(phenylene-vinylene) derivative,” Appl. Phys. Lett., 74(6): 865-867 (1999). [cited by applicant]
Guo, Tzung-Fang et al., “Highly Efficient Electrophosphorescent Polymer Light-Emitting Devices,” Organic Electronics, 1: 15-20 (2000). [cited by applicant]
Hamada, Yuji et al., “High Luminance in Organic Electroluminescent Devices with Bis(10-hydroxybenzo[h]quinolinato) beryllium as an Emitter,” Chem. Lett., 905-906 (1993). [cited by applicant]
Holmes, R.J. et al., “Blue Organic Electrophosphorescence Using Exothermic Host-Guest Energy Transfer,” Appl. Phys. Lett., 82(15):2422-2424 (2003). [cited by applicant]
Hu, Nan-Xing et al., “Novel High Tg Hole-Transport Molecules Based on Indolo[3,2-b]carbazoles for Organic Light-Emitting Devices,” Synthetic Metals, 111-112:421-424 (2000). [cited by applicant]
Huang, Jinsong et al., “Highly Efficient Red-Emission Polymer Phosphorescent Light-Emitting Diodes Based on Two Novel Tris(1-phenylisoquinolinato-C2,N)iridium(III) Derivatives,” Adv. Mater., 19:739-743 (2007). [cited by applicant]
Huang, Wei-Sheng et al., “Highly Phosphorescent Bis-Cyclometalated Iridium Complexes Containing Benzoimidazole-Based Ligands,” Chem. Mater., 16(12):2480-2488 (2004). [cited by applicant]
Hung, L.S. et al., “Anode Modification in Organic Light-Emitting Diodes by Low-Frequency Plasma Polymerization of CHF3,” Appl. Phys. Lett., 78(5):673-675 (2001). [cited by applicant]
Ikai, Masamichi et al., “Highly Efficient Phosphorescence From Organic Light-Emitting Devices with an Exciton-Block Layer,” Appl. Phys. Lett., 79(2):156-158 (2001). [cited by applicant]
Ikeda, Hisao et al., “P-185 Low-Drive-Voltage OLEDs with a Buffer Layer Having Molybdenum Oxide,” SID Symposium Digest, 37:923-926 (2006). [cited by applicant]
Inada, Hiroshi and Shirota, Yasuhiko, “1,3,5-Tris[4-(diphenylamino)phenyl]benzene and its Methylsubstituted Derivatives as a Novel Class of Amorphous Molecular Materials,” J. Mater. Chem., 3(3):319-320 (1993). [cited by applicant]
Kanno, Hiroshi et al., “Highly Efficient and Stable Red Phosphorescent Organic Light-Emitting Device Using bis[2-(2-benzothiazoyl)phenolato]zinc(II) as host material,” Appl. Phys. Lett., 90:123509-1-123509-3 (2007). [cited by applicant]
Kido, Junji et al., 1,2,4-Triazole Derivative as an Electron Transport Layer in Organic Electroluminescent Devices, Jpn. J. Appl. Phys., 32:L917-L920 (1993). [cited by applicant]
Kuwabara, Yoshiyuki et al., “Thermally Stable Multilayered Organic Electroluminescent Devices Using Novel Starburst Molecules, 4,4′,4″-Tri(N-carbazolyl)triphenylamine (TCTA) and 4,4′,4″-Tris(3-methylphenylphenyl-amino) … [cited by applicant]
Kwong, Raymond C. et al., “High Operational Stability of Electrophosphorescent Devices,” Appl. Phys. Lett., 81(1)162-164 (2002). [cited by applicant]
Lamansky, Sergey et al., “Synthesis and Characterization of Phosphorescent Cyclometalated Iridium Complexes,” Inorg. Chem., 40(7):1704-1711 (2001). [cited by applicant]
Lee, Chang-Lyoul et al., “Polymer Phosphorescent Light-Emitting Devices Doped with Tris(2-phenylpyridine) Iridium as a Triplet Emitter,” Appl. Phys. Lett., 77(15):2280-2282 (2000). [cited by applicant]
Lo, Shih-Chun et al., “Blue Phosphorescence from Iridium(III) Complexes at Room Temperature,” Chem. Mater., 18(21)5119-5129 (2006). [cited by applicant]
Ma, Yuguang et al., “Triplet Luminescent Dinuclear-Gold(I) Complex-Based Light-Emitting Diodes with Low Turn-On voltage,” Appl. Phys. Lett., 74(10):1361-1363 (1999). [cited by applicant]
Mi, Bao-Xiu et al., “Thermally Stable Hole-Transporting Material for Organic Light-Emitting Diode an Isoindole Derivative,” Chem. Mater., 15(16):3148-3151 (2003). [cited by applicant]
Nishida, Jun-ichi et al., “Preparation, Characterization, and Electroluminescence Characteristics of α-Diimine-type Platinum(II) Complexes with Perfluorinated Phenyl Groups as Ligands,” Chem. Lett., 34(4): 592-593 (2005… [cited by applicant]
Niu, Yu-Hua et al., “Highly Efficient Electrophosphorescent Devices with Saturated Red Emission from a Neutral Osmium Complex,” Chem. Mater., 17(13):3532-3536 (2005). [cited by applicant]
Noda, Tetsuya and Shirota, Yasuhiko, “5,5′-Bis(dimesitylboryl)-2,2′-bithiophene and 5,5″-Bis(dimesitylboryl)-2,2′5′,2″-terthiophene as a Novel Family of Electron-Transporting Amorphous Molecular Materials,” J. Am. Chem.… [cited by applicant]
Okumoto, Kenji et al., “Green Fluorescent Organic Light-Emitting Device with External Quantum Efficiency of Nearly 10%,” Appl. Phys. Lett., 89:063504-1-063504-3 (2006). [cited by applicant]
Palilis, Leonidas C., “High Efficiency Molecular Organic Light-Emitting Diodes Based On Silole Derivatives And Their Exciplexes,” Organic Electronics, 4:113-121 (2003). [cited by applicant]
Paulose, Betty Marie Jennifer S. et al., “First Examples of Alkenyl Pyridines as Organic Ligands for Phosphorescent Iridium Complexes,” Adv. Mater., 16(22):2003-2007 (2004). [cited by applicant]
Ranjan, Sudhir et al., “Realizing Green Phosphorescent Light-Emitting Materials from Rhenium(I) Pyrazolato Diimine Complexes,” Inorg. Chem., 42(4):1248-1255 (2003). [cited by applicant]
Sakamoto, Youichi et al., “Synthesis, Characterization, and Electron-Transport Property of Perfluorinated Phenylene Dendrimers,” J. Am. Chem. Soc., 122(8):1832-1833 (2000). [cited by applicant]
Salbeck, J. et al., “Low Molecular Organic Glasses for Blue Electroluminescence,” Synthetic Metals, 91: 209-215 (1997). [cited by applicant]
Shirota, Yasuhiko et al., “Starburst Molecules Based on pi-Electron Systems as Materials for Organic Electroluminescent Devices,” Journal of Luminescence, 72-74:985-991 (1997). [cited by applicant]
Sotoyama, Wataru et al., “Efficient Organic Light-Emitting Diodes with Phosphorescent Platinum Complexes Containing N [cited by applicant]
Sun, Yiru and Forrest, Stephen R., “High-Efficiency White Organic Light Emitting Devices with Three Separate Phosphorescent Emission Layers,” Appl. Phys. Lett., 91:263503-1-263503-3 (2007). [cited by applicant]
T. Östergård et al., “Langmuir-Blodgett Light-Emitting Diodes Of Poly(3-Hexylthiophene) Electro-Optical Characteristics Related to Structure,” Synthetic Metals, 88:171-177 (1997). [cited by applicant]
Takizawa, Shin-ya et al., “Phosphorescent Iridium Complexes Based on 2-Phenylimidazo[1,2-α]pyridine Ligands Tuning of Emission Color toward the Blue Region and Application to Polymer Light-Emitting Devices,” Inorg. Chem… [cited by applicant]
Tang, C.W. and VanSlyke, S.A., “Organic Electroluminescent Diodes,” Appl. Phys. Lett., 51(12):913-915 (1987). [cited by applicant]
Tung, Yung-Liang et al., “Organic Light-Emitting Diodes Based on Charge-Neutral Ru II PHosphorescent Emitters,” Adv. Mater., 17(8)1059-1064 (2005). [cited by applicant]
Van Slyke, S. A. et al., “Organic Electroluminescent Devices with Improved Stability,” Appl. Phys. Lett., 69 (15):2160-2162 (1996). [cited by applicant]
Wang, Y. et al., “Highly Efficient Electroluminescent Materials Based on Fluorinated Organometallic Iridium Compounds,” Appl. Phys. Lett., 79(4):449-451 (2001). [cited by applicant]
Wong, Keith Man-Chung et al., A Novel Class of Phosphorescent Gold(III) Alkynyl-Based Organic Light-Emitting Devices with Tunable Colour, Chem. Commun., 2906-2908 (2005). [cited by applicant]
Wong, Wai-Yeung, “Multifunctional Iridium Complexes Based on Carbazole Modules as Highly Efficient Electrophosphors,” Angew. Chem. Int. Ed., 45:7800-7803 (2006). [cited by applicant]
Chien, C.H., et al., “Stepwise and one-pot syntheses of Ir(III) Complexes with imidazolium-based carbene ligands,” Dalton Trans., 2008, pp. 916-923. [cited by applicant]
Li, Y., et al., “An N-heterocyclic carbene iridium catalysts with metal-centered chirality for enantioselective transfer hydrogenation of imines,” Chem. Commun., 2017, vol. 53, pp. 8089-8092. [cited by applicant]
Tronnier, A., et al., “(C [cited by applicant]
Schleicher, D., et al., “Cyclometalated Ruthenium(II) NHC Complexes with Imidazo[1,5-a]pyridine-Based (C [cited by applicant]
Li, L., et al., “Complementing Pyridin-2,6-bis(oxazoline) with Cyclometalated N-Heterocyclic Carbene for Asymmetric Ruthenium Catalysis,” Angew. Chem. Int., Ed., 2020, vol. 59, pp. 12392-12395. [cited by applicant]