US2022227799A1PendingUtilityA1
Organic electroluminescent materials and devices
Est. expiryOct 2, 2040(~14.2 yrs left)· nominal 20-yr term from priority
H10K 85/658C07F 15/0086H01L 51/0094H01L 51/0087H01L 51/0067H01L 51/0073H01L 51/0074H01L 51/008H01L 51/5004H01L 51/0072H01L 51/0054H01L 51/0058H01L 51/0056H10K 85/6572H10K 85/624H10K 85/626H10K 85/346H10K 50/11H10K 2101/10H10K 85/6576H10K 85/654H10K 85/40H10K 2101/90H10K 85/622H10K 85/6574H10K 2101/30H10K 2101/40H10K 85/615H10K 50/12H10K 85/322H10K 85/342
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Claims
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
exact text as granted — not AI-modifiedWhat is claimed is:
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 .Join the waitlist — get patent alerts
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