Organic electroluminescent materials and devices

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.