IP Library › Granted Patent US 12,686,696
Granted Patent B2
US 12,686,696 · App. 17/706,821 · Granted Jul 21, 2026

Organic electroluminescent materials and devices

Inventors: Elena Sheina (Langhorne, PA); Alexey Borisovich Dyatkin (Ambler, PA); George Fitzgerald (Lambertville, NJ); Jui-Yi Tsai (Newtown, PA); Hsiao-Fan Chen (Lawrence Township, NJ); Geza Szigethy (Newtown, PA)
Assignee: UNIVERSAL DISPLAY CORPORATION
C07F15/0086H10K85/346H10K50/11H10K2101/10H10K2101/30H10K2101/40
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 12,686,696
App. No.
17/706,821
Filed
Mar 29, 2022
Granted
Jul 21, 2026
Kind
B2
Art Unit
1759
USPC
428/690
Abstract

A compound including a tetradentate ligand, L A , is provided. In the compound, L A is coordinated to a metal M selected from Pt, Pd, Cu, Ag, and Au; L A comprises a first moiety and a second moiety that are different form each other and are independently coordinated to the metal M; the first moiety is a heterocyclic carbene, that is coordinated to the metal M through a metal-carbene bond, while the second moiety is a 5-membered heterocycle; and the ligand L A forms at least one M-O or M-S bond. Formulations, OLEDs, and consumer products containing the compound are also provided.

Claims (135)

1 . A compound comprising a tetradentate ligand, L A , wherein:

L A is coordinated to a metal M, which is selected from the group consisting of Pt, Pd, Cu, Ag, and Au;

L A comprises a first moiety and a second moiety;

the first and the second moieties are both coordinated to the metal M;

the first moiety and the second moiety are different from one another;

the first moiety is a heterocyclic carbene, which coordinates to the metal M through a metal-carbene bond;

the second moiety is a 5-membered heterocycle;

ligand L A forms at least one M-K bond; and

K is a bivalent O or S; with the proviso that:

1) The compound does not comprise a moiety,

 wherein K′ is selected from the group consisting of a direct bond, O, and S, and Y is selected from the group consisting of NR, O, S, and Se; and

2) when the compound comprises two M-O bonds, then the first moiety is not an N-heterocyclic carbene.

2 . The compound of claim 1 , wherein the first moiety is selected from the group consisting of imidazole-derived carbene and benzimidazole-derived carbene.

3 . The compound of claim 1 , wherein the second moiety is selected form the group consisting of imidazole-derived carbene, pyrrole, pyrazole, oxazole, furan, thiophene, thiazole, indole, isoindole, triazole, imidazo[1,2-a]imidazole and benzo[d]imidazo[1,2-a]imidazole.

4 . The compound of claim 1 , further comprising a third moiety and a fourth moiety that are coordinated to the metal M, wherein each of the first, second, third, and fourth moieties are different from one another.

5 . The compound of claim 4 , wherein each of the third and fourth moieties is independently a 5-membered or 6-membered carbocyclic or heterocyclic ring.

6 . The compound of 4 , wherein exactly one of the third moiety and the fourth moiety is joined to the metal M by K.

7 . A compound of claim 1 , comprising the structure of Formula I:

wherein:

each of rings B, C, and D is independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

M is Pt or Pd;

ring A coordinates to M through a metal-carbene bond;

at least one of rings B, C, and D is a 5-membered ring;

X 1 , X 2 , and X 3 , X 4 , and X 5 are each independently C or N;

at least one of X 1 , X 2 , and X 3 is N;

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

Z 1 , Z 2 , and Z 3 are each independently C or N;

each of K 1 and K 2 is independently selected from the group consisting of a direct bond, O, and S;

at least one of K 1 and K 2 is not a direct bond;

if K 1 and K 2 are both oxygen, then ring C is not an N-heterocyclic carbene;

each is independently a single bond or a double bond;

R A , R B , R C , and R D each independently represents mono to the maximum allowable substitution, or no substitution;

L 1 and L 2 are each independently selected from the group consisting of a direct bond, BR, BRR′, NR, PR, P(O)R, O, S, Se, C═O, C═S, C═Se, C═NR, C═CRR′, S═O, SO 2 , CR, CRR′, SiRR′, GeRR′, alkylene, cycloalkyl, aryl, cycloalkylene, arylene, heteroarylene, and combinations thereof;

each R, R′, R A , R B , R C , and R D is independently hydrogen or a substituent selected from the group consisting of the general substituents defined herein; and

any two substituents may be joined or fused together to form a ring.

8 . The compound of claim 7 , wherein each R, R′, R A , R B , R C , and R D is independently 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.

9 . The compound of claim 7 , wherein each of rings B, C, and D is independently selected from the group consisting of benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, and thiazole, indole, isoindole, triazole, imidazo[1,2-a]imidazole, and benzo[d]imidazo[1,2-a]imidazole.

10 . The compound of claim 7 , wherein exactly one of X 1 , X 2 , and X 3 is N.

11 . The compound of claim 7 , wherein both Y 1 and Y 2 are C.

12 . The compound of claim 7 , wherein exactly one of K 1 and K 2 is O or S.

13 . The compound of claim 7 , wherein at least one of L 1 and L 2 is not a direct bond.

14 . The compound of claim 7 , wherein the compound has a structure selected from the group consisting of:

wherein:

each of X 4 , X 5 , X 6 , and X 7 is independently C or N;

R K , R L , R M , R N , and R O each independently represents mono to the maximum allowable substitution, or no substitution; and

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

15 . The compound of claim 1 , wherein the compound has formula PtW—(Ro)(Rp)(Rq)(Rr)(Rs)(Rf), wherein W is an integer from 1 to 47 or 50 to 54, each o, p, q, r, s, and t is independently an integer from 1 to 88, and the compound is selected from the group consisting of Pt1-(R1)(R1)(R1)(R1)(R1)(R1) to Pt54-(R88)(R88)(R88)(R88)(R88)(R88), defined by the structures of the following table:

Structure of PtW

Pt1-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt1- (R1)(R1)(R1)(R1)(R1)(R1) to Pt1- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt2-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt2- (R1)(R1)(R1)(R1)(R1)(R1) to Pt2- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt3-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt3- (R1)(R1)(R1)(R1)(R1)(R1) to Pt3- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt4-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt4- (R1)(R1)(R1)(R1)(R1)(R1) to Pt4- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt5-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt5- (R1)(R1)(R1)(R1)(R1)(R1) to Pt5- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt6-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt6- (R1)(R1)(R1)(R1)(R1)(R1) to Pt6- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt7-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt7- (R1)(R1)(R1)(R1)(R1)(R1) to Pt7- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt8-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt8- (R1)(R1)(R1)(R1)(R1)(R1) to Pt8- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt9-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt9- (R1)(R1)(R1)(R1)(R1)(R1) to Pt9- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt10-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt10- (R1)(R1)(R1)(R1)(R1)(R1) to Pt10- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt11-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt11- (R1)(R1)(R1)(R1)(R1)(R1) to Pt11- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt12-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt12- (R1)(R1)(R1)(R1)(R1)(R1) to Pt12- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt13-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt13- (R1)(R1)(R1)(R1)(R1)(R1) to Pt3- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt14-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt14- (R1)(R1)(R1)(R1)(R1)(R1) to Pt14- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt15-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt15- (R1)(R1)(R1)(R1)(R1)(R1) to Pt15- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt16-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt16- (R1)(R1)(R1)(R1)(R1)(R1) to Pt16- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt17-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt17- (R1)(R1)(R1)(R1)(R1)(R1) to Pt17- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt18-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt18- (R1)(R1)(R1)(R1)(R1)(R1) to Pt18- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt19-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt19- (R1)(R1)(R1)(R1)(R1)(R1) to Pt19- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt20-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt20- (R1)(R1)(R1)(R1)(R1)(R1) to Pt20- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt21-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt21- (R1)(R1)(R1)(R1)(R1)(R1) to Pt21- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt22-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt22- (R1)(R1)(R1)(R1)(R1)(R1) to Pt22- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt23-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt23- (R1)(R1)(R1)(R1)(R1)(R1) to Pt23- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt24-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt24- (R1)(R1)(R1)(R1)(R1)(R1) to Pt24- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt25-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt25- (R1)(R1)(R1)(R1)(R1)(R1) to Pt25- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt26-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt26- (R1)(R1)(R1)(R1)(R1)(R1) to Pt26- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt27-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt27- (R1)(R1)(R1)(R1)(R1)(R1) to Pt27- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt28-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt28- (R1)(R1)(R1)(R1)(R1)(R1) to Pt28- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt29-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt29- (R1)(R1)(R1)(R1)(R1)(R1) to Pt29- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt30-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt30- (R1)(R1)(R1)(R1)(R1)(R1) to Pt30- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt31-(Ro)(Rp)(Rg)(Rr)(Rs)(Rt), wherein Pt31- (R1)(R1)(R1)(R1)(R1)(R1) to Pt31- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt32-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt32- (R1)(R1)(R1)(R1)(R1)(R1) to Pt32- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt33-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt33- (R1)(R1)(R1)(R1)(R1)(R1) to Pt33- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt34-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt34- (R1)(R1)(R1)(R1)(R1)(R1) to Pt34- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt35-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt35- (R1)(R1)(R1)(R1)(R1)(R1) to Pt35- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt36-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt36- (R1)(R1)(R1)(R1)(R1)(R1) to Pt36- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt37-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt37- (R1)(R1)(R1)(R1)(R1)(R1) to Pt37- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt38-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt38- (R1)(R1)(R1)(R1)(R1)(R1) to Pt38- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt39-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt39- (R1)(R1)(R1)(R1)(R1)(R1) to Pt39- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt40-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru), wherein Pt40- (R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt40- (R88)(R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt41-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru), wherein Pt41- (R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt41- (R88)(R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt42-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt42- (R1)(R1)(R1)(R1)(R1)(R1) to Pt42- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt43-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt43- (R1)(R1)(R1)(R1)(R1)(R1) to Pt43- (R88)(R88)(R88)(R88)(R88)(R88), have the structure

Pt44-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt44- (R1)(R1)(R1)(R1)(R1)(R1) to Pt44- (R88)(R88)(R88)(R88)(R88)(R88), have the structure,

Pt45-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt45- (R1)(R1)(R1)(R1)(R1)(R1) to Pt45- (R88)(R88)(R88)(R88)(R88)(R88), have the structure,

Pt46-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt46- (R1)(R1)(R1)(R1)(R1)(R1) to Pt46- (R88)(R88)(R88)(R88)(R88)(R88), have the structure,

Pt47-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt47- (R1)(R1)(R1)(R1)(R1)(R1) to Pt47- (R88)(R88)(R88)(R88)(R88)(R88), have the structure,

Pt50-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt50- (R1)(R1)(R1)(R1)(R1)(R1) to Pt50- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt51-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt51- (R1)(R1)(R1)(R1)(R1)(R1) to Pt51- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt52-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt52- (R1)(R1)(R1)(R1)(R1)(R1) to Pt52- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt53-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt53- (R1)(R1)(R1)(R1)(R1)(R1) to Pt53- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt54-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt54- (R1)(R1)(R1)(R1)(R1)(R1) to Pt54- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

wherein R 1 to R88 have the following structures:

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

17 . 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 tetradentate ligand, L A , wherein:

L A is coordinated to a metal M, which is selected from the group consisting of Pt, Pd, Cu, Ag, and Au;

L A comprises a first moiety and a second moiety;

the first and the second moieties are both coordinated to the metal M;

the first moiety and the second moiety are different from one another;

the first moiety is a heterocyclic carbene, which coordinates to the metal M through a metal-carbene bond;

the second moiety is a 5-membered heterocycle;

ligand L A forms at least one M-K bond; and

K is a bivalent O or S; with the proviso that:

1) The compound does not comprise a moiety,

 wherein K′ is selected from the group consisting of a direct bond, O, and S, and Y is selected from the group consisting of NR, O, S, and Se; and

2) when the compound comprises two M-O bonds, then the first moiety is not an N-heterocyclic carbene.

18 . The OLED of claim 17 , 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, 522-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, triazine, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, and aza-(5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene).

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

and combinations thereof.

20 . 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, wherein the organic layer comprises a compound comprising a tetradentate ligand, L A , wherein:

L A is coordinated to a metal M, which is selected from the group consisting of Pt, Pd, Cu, Ag, and Au;

L A comprises a first moiety and a second moiety;

the first and the second moieties are both coordinated to the metal M;

the first moiety and the second moiety are different from one another;

the first moiety is a heterocyclic carbene, which coordinates to the metal M through a metal-carbene bond;

the second moiety is a 5-membered heterocycle;

ligand L A forms at least one M-K bond; and

K is a bivalent O or S; with the proviso that:

1) The compound does not comprise a moiety,

 wherein K′ is selected from the group consisting of a direct bond, O, and S, and Y is selected from the group consisting of NR, O, S, and Se; and

2) when the compound comprises two M-O bonds, then the first moiety is not an N-heterocyclic carbene.

Assignments (2)
CORRECTIVE ASSIGNMENT TO CORRECT THE SECOND INVENTOR'S NAME PREVIOUSLY RECORDED AT REEL: 059422 FRAME: 0986. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT . Recorded Mar 31, 2022
From: SHEINA, ELENA; DYATKIN, ALEXEY BORISOVICH; FITZGERALD, GEORGE; TSAI, JUI-YI; CHEN, HSIAO-FAN; SZIGETHY, GEZA
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 059555/0231 →
NUNC PRO TUNC ASSIGNMENT Recorded Mar 29, 2022
From: SHEINA, ELENA; DYATKIN, A BORISOVICH; FITZGERALD, GEORGE; TSAI, JUI-YI; CHEN, HSIAO-FAN; SZIGETHY, GEZA
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 059422/0986 →
Continuity (6)
Provisional Application 63314827 · Feb 28, 2022
Provisional Application 63310330 · Feb 15, 2022
Provisional Application 63266781 · Jan 14, 2022
Provisional Application 63262587 · Oct 15, 2021
Provisional Application 63262247 · Oct 8, 2021
Related Publication 20230147616A1 · May 11, 2023
References Cited (189)
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 8957217B2 · Che et al. · 2015 [cited by applicant]
US 9935277B2 · Xia et al. · 2018 [cited by applicant]
US 10135008B2 · Lin et al. · 2018 [cited by applicant]
US 10144867B2 · Ma · 2018 [cited by examiner]
US 10889754B2 · Ma et al. · 2021 [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 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 20150194615A1 · Lin · 2015 [cited by examiner]
US 20150214494A1 · Xia et al. · 2015 [cited by applicant]
US 20190074458A1 · Lee et al. · 2019 [cited by applicant]
US 20200220090A1 · Chen et al. · 2020 [cited by applicant]
US 20210095195A1 · Ma et al. · 2021 [cited by applicant]
US 20210151696A1 · Lee · 2021 [cited by examiner]
US 20210175444A1 · Yi et al. · 2021 [cited by applicant]
US 20210380620A1 · Kim et al. · 2021 [cited by applicant]
CN 109810106 · 2019 [cited by applicant]
CN 112939940 · 2021 [cited by applicant]
CN 112940041 · 2021 [cited by applicant]
EP 0650955 · 1995 [cited by applicant]
EP 1725079 · 2006 [cited by applicant]
EP 2034538 · 2009 [cited by applicant]
EP 3613752 · 2020 [cited by applicant]
EP 3450441 · 2020 [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 2009267176 · 2009 [cited by applicant]
KR 20190085190 · 2019 [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 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 a-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 ridium 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. Östergard 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. Che… [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]