Organic electroluminescent materials and devices

Abstract

The present invention discloses novel Pt(IV) compounds useful for enhancing the performance of organic electroluminescent devices.

We claim: 
     
         1 . A compound having the formula Pt(L) n ;
 wherein Pt is Pt(IV) metal, L is a ligand coordinating to Pt, and n is an integer from 1 to 3;   wherein each L can be the same or different, and L is selected from the group consisting of bidentate, tridentate, tetradentate and hexadentate;   wherein the Pt has an octahedral coordinating geometry, and   wherein the compound is neutral.   
     
     
         2 . The compound of  claim 1 , wherein the compound is selected from the group consisting of PtL 1 L 2 , PtL 3 L 4 , and PtL 1 L 5 L 6 ;
 wherein L 1 , L 5 , and L 6  are bidentate ligands; L 2  is tetradentate ligand; L 3  and L 4  are tridentate ligands; and   wherein within each compound, all ligands are optionally joined together to form a tetradentate or a hexadentate ligand.   
     
     
         3 . The compound of  claim 1 , wherein each L is independently selected from the group consisting of: 
       
         
           
           
               
               
           
         
         wherein X is a neutral coordinating atom selected from the group consisting of carbene, carbon, phosphorus, and nitrogen and each X can be the same or different; 
         wherein Y is an anionic coordinating atom selected from the group consisting of carbon, nitrogen, and oxygen atom and each Y can be the same or different; 
       
     
     
         4 . The compound of  claim 3 , wherein the neutral carbene carbon is an N-heterocyclic carbene carbon; wherein the neutral phosphorus is a phosphorus atom of a trisubstituted phosphine; and wherein the neutral nitrogen is an sp 2  nitrogen atom of an N-heterocyclic ring selected from the group consisting of pyridine, imidazole, pyrazole, and triazole. 
     
     
         5 . The compound of  claim 3 , wherein the anionic coordinating carbon is an sp 2  carbon atom selected from the group consisting of benzene, pyridine, furan, thiophene, and pyrrole. 
     
     
         6 . The compound of  claim 3 , wherein the anionic coordinating nitrogen is an sp 2  nitrogen atom of an N-heterocyclic ring selected from the group consisting of imidazole, pyrazole, pyrrole, and triazole. 
     
     
         7 . The compound of  claim 3 , wherein the anionic oxygen atom is an oxygen atom from a carboxylic acid or an ether. 
     
     
         8 . The compound of  claim 3 , wherein the compound is selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
     
     
         9 . The compound of  claim 3 , wherein the compound is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein R A , R B , R C , R D , R E , R F , R G , R, and R′ each independently represent mono to the maximum possible number of substitutions, or no substitution; 
         wherein Y is selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, and GeRR′; 
         wherein R A , R B , R C , R D , R E , R F , R G , R, R′ and Z are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, aryl, heteroaryl, alkoxy, aryloxy, amino, silyl, and combinations thereof; and 
         wherein any adjacent R A , R B , R C , R D , R E , R F , R G , R, and R′ are optionally joined to form a ring. 
       
     
     
         10 . The compound of  claim 3 , wherein the compound is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         11 . An organic light emitting device (OLED) comprising:
 an anode;   a cathode; and   an organic layer, disposed between the anode and the cathode, comprising a compound having the formula Pt(L) n ;   wherein Pt is Pt(IV) metal, L is a ligand coordinating to Pt, and n is an integer from 1 to 3;   wherein each L can be the same or different, and L is selected from the group consisting of bidentate, tridentate, tetradentate and hexadentate;   wherein the Pt has an octahedral coordinating geometry, and   wherein the compound is neutral.   
     
     
         12 . The OLED of  claim 11 , wherein the OLED is selected from the group consisting of a consumer product, an electronic component module, an organic light-emitting device, and a lighting panel. 
     
     
         13 . The OLED of  claim 11 , wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant. 
     
     
         14 . The OLED of  claim 11 , wherein the organic layer further comprises a host, wherein the host comprises a triphenylene containing benzo-fused thiophene or benzo-fused furan;
 wherein any substituent in the host is an unfused substituent independently selected from the group consisting of C n H 2n+1 , OC n H 2n+1 , OAr 1 , N(C n H 2n+1 ) 2 , N(Ar 1 )(Ar 2 ), CH═CH—C n H 2n+1 , CECC n H 2n+1 , Ar 1 , Ar 1 -Ar 2 , C n H 2n —Ar 1 ;   wherein n is from 1 to 10; and   wherein Ar 1  and Ar 2  are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.   
     
     
         15 . The OLED of  claim 11 , wherein the organic layer further comprises a host, wherein host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiphene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene. 
     
     
         16 . The OLED of  claim 11 , wherein the organic layer further comprises a host, wherein the host is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       and combinations thereof. 
     
     
         17 . The OLED of  claim 11 , wherein the organic layer further comprises a host, wherein the host comprises a metal complex. 
     
     
         18 . 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, comprising a compound having the formula Pt(L) n ;   wherein Pt is Pt(IV) metal, L is a ligand coordinating to Pt, and n is an integer from 1 to 3;   wherein each L can be the same or different, and L is selected from the group consisting of bidentate, tridentate, tetradentate and hexadentate;   wherein the Pt has an octahedral coordinating geometry, and   wherein the compound is neutral.   
     
     
         19 . The consumer product of  claim 18 , wherein the consumer product is selected from the group consisting of a flat panel display, a computer monitor, a medical monitors television, a billboard, a light for interior or exterior illumination and/or signaling, a heads-up display, a fully or partially transparent display, a flexible display, a laser printer, a telephone, a cell phone, tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro-display that is less than 2 inches diagonal, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video walls comprising multiple displays tiled together, a theater or stadium screen, and a sign.