Organic electroluminescent materials and devices

Abstract

Fluorine substituted metal complexes as efficient phosphorescent emitters is disclosed. The fluorine substitution is at para position of a phenyl group.

We claim: 
     
         1 . A compound having a structure according to Formula I: 
       
         
           
           
               
               
           
         
         wherein R 1 , R 2 , and R 3  each independently represent mono, di, tri, or tetra substitutions, or no substitution; 
         wherein R 1  is selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, and combinations thereof; 
         wherein R 2  and R 3  are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and 
         wherein the compound is heteroleptic. 
       
     
     
         2 . The compound of  claim 1 , wherein R 1  is hydrogen or deuterium. 
     
     
         3 . The compound of  claim 1 , wherein R 2  and R 3  are independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, and combinations thereof. 
     
     
         4 . The compound of  claim 1 , wherein the compound has a structure according to Formula II: 
       
         
           
           
               
               
           
         
       
     
     
         5 . The compound of  claim 1 , wherein the compound has a structure according to Formula III: 
       
         
           
           
               
               
           
         
       
     
     
         6 . The compound of  claim 1 , wherein the compound is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         7 . A compound comprising a ligand L, wherein L is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein R a , R b , R c , and R d  each independently represent from mono-substitution to the possible maximum number of substitution, or no substitution; 
         wherein R a , R b , R c , and R d  are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; 
         wherein two adjacent substituents of R a , R b , R c , and R d  are optionally joined to form a ring or form a multidentate ligand; 
         wherein at least one of R a , R b , and R d  comprises 4-fluoro-phenyl; and 
         wherein the ligand L is coordinated to a metal M selected from the group consisting of Ir, Pt, Os, Re, Ru, Rh, Pd, Ag, Au, and Cu. 
       
     
     
         8 . The compound of  claim 7 , wherein L is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         9 . The compound of  claim 7 , wherein metal M is Ir or Pt. 
     
     
         10 . The compound of  claim 7 , wherein the compound is heteroleptic. 
     
     
         11 . The compound of  claim 7 , wherein the compound is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein R e , R f , and R g  each independently represent from mono-substitution to the possible maximum number of substitution, or no substitution; and 
         wherein R e , R f , and R g  are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof. 
       
     
     
         12 . The compound of  claim 7 , wherein the compound is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein R e , R f , R g , and R h  each independently represent from mono-substitution to the possible maximum number of substitution, or no substitution; 
         wherein R e , R f , R g  and R h  are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; 
         wherein X is selected from the group consisting of a single bond, BR, NR, O, Se, C═O, S═O, SO 2 , CRR′, SiRR′, and GeRR′; 
         wherein R and R′ are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and 
         wherein two adjacent substituents of R and R′ are optionally joined to form a ring. 
       
     
     
         13 . The compound of  claim 7 , wherein the compound is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         14 . The compound of  claim 7 , wherein the compound is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein X is selected from the group consisting of a single bond, BR, NR, O, Se, C═O, S═O, SO 2 , CRR′, SiRR′, and GeRR′; 
         wherein R and R′ are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and 
         wherein two adjacent substituents of R and R′ are optionally joined to form a ring. 
       
     
     
         15 . A first device comprising a first organic light emitting device, the first organic light emitting device comprising:
 an anode;   a cathode; and   an organic layer, disposed between the anode and the cathode, comprising a compound having a structure according to Formula I:   
       
         
           
           
               
               
           
         
         wherein R 1 , R 2 , and R 3  each independently represent mono, di, tri, or tetra substitutions, or no substitution; 
         wherein R 1  is selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, and combinations thereof; 
         wherein R 2  and R 3  are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and 
         wherein the compound is heteroleptic. 
       
     
     
         16 . A first device comprising a first organic light emitting device, the first organic light emitting device comprising:
 an anode;   a cathode; and   an organic layer, disposed between the anode and the cathode, comprising a compound comprising a ligand L, wherein L is selected from the group consisting of:   
       
         
           
           
               
               
           
         
         wherein R a , R b , R e , and R d  each independently represent from mono-substitution to the possible maximum number of substitution, or no substitution; 
         wherein R a , R b , R c , and R d  are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; 
         wherein two adjacent substituents of R a , R b , R c , and R d  are optionally joined to form a ring or form a multidentate ligand; 
         wherein at least one of R a , R b , and R d  is 4-fluoro-phenyl; and 
         wherein the ligand L is coordinated to a metal M selected from the group consisting of Ir, Pt, Os, Re, Ru, Rh, Pd, Ag, Au, and Cu. 
       
     
     
         17 . The first device of  claim 15  or  16 , wherein the first device is selected from the group consisting of a consumer product, an electronic component module, an organic light-emitting device, and a lighting panel. 
     
     
         18 . The first device of  claim 15  or  16 , wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant. 
     
     
         19 . The first device of  claim 15  or  16 , 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 , C≡CC n H 2n+1 , Ar 1 , Ar 1 -Ar 2 , C n H 2n —Ar 1 , or no substitution; 
 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. 
 
     
     
         20 . The first device of  claim 15  or  16 , wherein the organic layer further comprises a host, wherein the 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. 
     
     
         21 . The first device of  claim 15  or  16 , wherein the organic layer further comprises a host, wherein the host is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       and combinations thereof. 
     
     
         22 . The first device of  claim 15  or  16 , wherein the organic layer further comprises a host, wherein the host comprises a metal complex. 
     
     
         23 . A formulation comprising a compound in  claim 1  or  claim 7 .