IP Library › Patent Application 17656895

Patent Application

App. No. 17/656,895

ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES

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 None
App. No.: 17/656,895

External Links

USPTO Patent Center↗ Full Patent PDF↗

Abstract

Provided are compounds containing platinum which is coordinated by a tetradentate ligand wherein the tetradentate ligand comprises at least one five-membered ring comprising at least one nitrogen atom which is fused to a further five- or six membered ring. Also provided are formulations comprising these compounds. Further provided are OLEDs and related consumer products that utilize these compounds.

Claims (116)

1 . A compound comprising a structure of Formula I or Formula II,

wherein:

M is Pt or Pd;

Rings B, C, and D are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

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

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

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

K is O or S;

is a single bond or double bond;

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

L is selected from the group consisting of a BR, BRR′, NR, PR, O, S, Se, C═X, S═O, SO 2 , CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof;

X is independently selected from the group consisting of O, S, NR and CRR′;

each R′, R″, R A , R B , R C , R D , and R E 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, boryl, selenyl, and combinations thereof;

R is hydrogen or a substituent selected from the group consisting of deuterium, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof; and

any two R, R′, R A , R B , R C , R D , and R E may be joined or fused together to form a ring.

2 . The compound of claim 1 , wherein at least three of X 1 -X 4 are C.

3 . The compound of claim 1 , wherein all of X 1 -X 4 are C.

4 . The compound of claim 1 , wherein K is O.

5 . The compound of claim 1 , wherein exactly one of Z 1 , Z 2 , and Z 3 is N.

6 . The compound of claim 1 , wherein exactly two of Z 1 , Z 2 , and Z 3 are N.

7 . The compound of claim 1 , wherein all of rings B, C, and D are six-membered rings.

8 . The compound of claim 1 , wherein at least one of rings B, C, and D is a five-membered ring.

9 . The compound of claim 1 , wherein the compound comprises a guanidine group.

10 . The compound of claim 1 , wherein two R E are joined together to form a six-membered aromatic ring, or two R E are joined together to form a five-membered aromatic ring.

11 . The compound of claim 1 , wherein L is selected from the group consisting of O, NR, CR, and CRR′.

12 . The compound of claim 1 , wherein L is CRR′ and R is joined or fused with one of R B , R C , or R D to form a ring.

13 . The compound of claim 1 , wherein each R′, R A , R B , R C , R D , and R E 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, a metal atom, and combinations thereof.

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

wherein R E′ and R F have the same definition as R A , R B , R C , R D , and R E ; and

wherein Y is selected from the group consisting of BR, BRR′, NR, PR, O, S, Se, C═X, S═O, SO 2 , CR, CRR′, SiRR′, and GeRR′, wherein X, R and R′ are as defined above.

15 . The compound of claim 1 , wherein the compound is selected from the group consisting of the following compounds:

Structure of PtA

Pt1-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt1- (R1)(R1)(R1)(R1)(R1)(R1) to Pt1- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt2-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt2- (R1)(R1)(R1)(R1)(R1)(R1) to Pt2- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt3-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt3- (R1)(R1)(R1)(R1)(R1)(R1) to Pt3- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt4-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt4- (R1)(R1)(R1)(R1)(R1)(R1) to Pt4- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt5-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt5- (R1)(R1)(R1)(R1)(R1)(R1) to Pt5- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt6-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt6- (R1)(R1)(R1)(R1)(R1)(R1) to Pt6- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt7-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru), wherein Pt7- (R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt7- (R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt8-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru), wherein Pt8- (R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt4- (R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt9-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru), wherein Pt9- (R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt9- (R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt10-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru), wherein Pt10- (R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt10- (R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt11-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru), wherein Pt11- (R1)(R1)(R1)(R1)(R1)(R1)(R1) to P11- (R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt12-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru), wherein Pt12- (R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt12- (R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt13-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru), wherein Pt13- (R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt13- (R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt14-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru), wherein Pt14- (R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt14- (R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt15-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru), wherein Pt15- (R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt15- (R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt16-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru), wherein Pt16- (R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt16- (R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt17-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru), wherein Pt17- (R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt17- (R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt18-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru), wherein Pt18- (R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt18- (R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt19-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru)(Rv), wherein Pt19- (R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt19- (R86)(R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt20-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru)(Rv), wherein Pt20- (R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt20- (R86)(R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt21-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru)(Rv), wherein Pt21- (R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt21- (R86)(R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt22-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru)(Rv), wherein Pt22- (R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt22- (R86)(R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt23-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru)(Rv), wherein Pt23- (R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt23- (R86)(R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt24-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru)(Rv), wherein Pt24- (R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt24- (R86)(R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt25-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru), wherein Pt25- (R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt25- (R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt26-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru), wherein Pt26- (R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt26- (R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt27-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru), wherein Pt27- (R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt27- (R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt28-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru), wherein Pt27- (R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt28- (R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt29-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru), wherein Pt29- (R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt29- (R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt30-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru), wherein Pt30- (R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt30- (R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt31-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru), wherein Pt31- (R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt31- (R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt32-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru), wherein Pt32- (R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt32- (R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt33-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru)(Rv), wherein Pt33- (R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt33- (R86)(R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt34-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru)(Rv), wherein Pt34- (R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt34- (R86)(R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt35-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru)(Rv), wherein Pt35- (R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt35- (R86)(R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt36-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru)(Rv), wherein Pt36- (R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt36- (R86)(R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt37-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru)(Rv)(Rw), wherein Pt37-(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt37- (R86)(R86)(R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt38-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt)(Ru)(Rv)(Rw), wherein Pt38-(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to Pt38- (R86)(R86)(R86)(R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt39-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt39- (R1)(R1)(R1)(R1)(R1)(R1) to Pt39- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt40-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt40- (R1)(R1)(R1)(R1)(R1)(R1) to Pt40- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt41-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt41- (R1)(R1)(R1)(R1)(R1)(R1) to Pt41- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt42-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt42- (R1)(R1)(R1)(R1)(R1)(R1) to Pt42- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt43-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt43- (R1)(R1)(R1)(R1)(R1)(R1) to Pt43- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt44-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt44- (R1)(R1)(R1)(R1)(R1)(R1) to Pt44- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt45-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt45- (R1)(R1)(R1)(R1)(R1)(R1) to Pt45- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt46-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt46- (R1)(R1)(R1)(R1)(R1)(R1) to Pt46- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt47-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt47- (R1)(R1)(R1)(R1)(R1)(R1) to Pt47- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt48-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt48- (R1)(R1)(R1)(R1)(R1)(R1) to Pt47- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt49-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt49- (R1)(R1)(R1)(R1)(R1)(R1) to Pt49- (R86)(R86)(R86)(R86)(R86)(R86), 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

Pt55-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt55- (R1)(R1)(R1)(R1)(R1)(R1) to Pt55- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt56-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt56- (R1)(R1)(R1)(R1)(R1)(R1) to Pt56- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt57-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt57- (R1)(R1)(R1)(R1)(R1)(R1) to Pt57- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt58-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt58- (R1)(R1)(R1)(R1)(R1)(R1) to Pt58- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt59-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt59- (R1)(R1)(R1)(R1)(R1)(R1) to Pt59- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt60-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt60- (R1)(R1)(R1)(R1)(R1)(R1) to Pt60- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt61-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt61- (R1)(R1)(R1)(R1)(R1)(R1) to Pt61- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt62-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt62- (R1)(R1)(R1)(R1)(R1)(R1) to Pt62- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt63-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt63- (R1)(R1)(R1)(R1)(R1)(R1) to Pt63- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt64-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt64- (R1)(R1)(R1)(R1)(R1)(R1) to Pt64- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt65-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt65- (R1)(R1)(R1)(R1)(R1)(R1) to Pt65- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

Pt66-(Ro)(Rp)(Rq)(Rr)(Rs)(Rt), wherein Pt66- (R1)(R1)(R1)(R1)(R1)(R1) to Pt66- (R86)(R86)(R86)(R86)(R86)(R86), have the structure

wherein R o is Ro, R p is Rp, R q is Rq, R r is Rr, R s is Rs, R t is Rt, is Ru, R v is Rv, and R w is Rw, and

wherein o, p, q, r, s, t, u, v, and w are each independently an integer from 1 to 86, and

wherein R1 to R86 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 according to claim 1 .

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, dibenzothiphene, dibenzofuran, dibenzoselenophene, 5λ2-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 (OLED) comprising:

an anode;

a cathode; and

an organic layer disposed between the anode and the cathode,

wherein the organic layer comprises a compound according to claim 1 .

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 29, 2022

From: FELDMAN, JERALD; CHEN, HSIAO-FAN; DYATKIN, ALEXEY BORISOVICH; FLEETHAM, TYLER; JRADI, FADI M.

To: UNIVERSAL DISPLAY CORPORATION

Reel/Frame 059420/0779 →