Organic electroluminescence device and electronic apparatus provided with the same

Abstract

An organic electroluminescence device including a cathode, an anode, and an emitting layer disposed between the cathode and the anode, wherein the emitting layer includes a compound represented by the following formula (1) and one or more compounds selected from the group consisting of compounds represented by formulas (11), (21), (31), (41), (51), (61), (71) and (81), In the formula (1), at least one of R 1 to R 8 is a deuterium atom,

1 . An organic electroluminescence device comprising:
 a cathode,   an anode, and   an emitting layer disposed between the cathode and the anode, wherein   the emitting layer comprises a compound represented by the following formula (1) and one or more compounds selected from a group consisting of the following formulas (32), (34-2) and (35-2):   
       
         
           
           
               
               
           
         
         wherein in the formula (1), 
         R 1  to R 8  are independently 
       
       a hydrogen atom, 
       a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, 
       a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, 
       a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, 
       a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, 
       —Si(R 901 )(R 902 )(R 903 ), 
       —O—(R 904 ), 
       —S—(R 905 ), 
       —N(R 906 )(R 907 ), 
       a halogen atom, a cyano group, a nitro group, 
       a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or 
       a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;
 R 901  to R 907  are independently 
 
       a hydrogen atom, 
       a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, 
       a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, 
       a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or 
       a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;
 when two or more of R 901  to R 907  exist, two or more of R 901  to R 907  may be the same with or different from each other; 
 at least one of R 1  to R 8  is a deuterium atom; 
 two or more adjacent groups of R 1  to R 4  and two or more adjacent groups of R 5  to R 8  do not form a ring; 
 L 1  and L 2  are independently 
 
       a single bond, 
       a substituted or unsubstituted phenylene group, 
       a substituted or unsubstituted naphthylene group, 
       a substituted or unsubstituted biphenylene group, 
       a substituted or unsubstituted terphenylene group, 
       a substituted or unsubstituted anthrylene group, or 
       a substituted or unsubstituted phenanthrylene group;
 Ar 1  and Ar 2  are independently 
 
       a substituted or unsubstituted phenyl group, 
       a substituted or unsubstituted naphthyl group, 
       a substituted or unsubstituted biphenyl group, 
       a substituted or unsubstituted terphenyl group, 
       a substituted or unsubstituted anthryl group, or 
       a substituted or unsubstituted phenanthryl group;
 when L 1 , L 2 , Ar 1  and Ar 2  have a substituent, the substituent is 
 
       an alkyl group having 1 to 50 carbon atoms, 
       an alkenyl group having 2 to 50 carbon atoms, 
       an alkynyl group having 2 to 50 carbon atoms, 
       a cycloalkyl group having 3 to 50 ring carbon atoms, 
       an alkylsilyl group having 1 to 50 carbon atoms, 
       a halogen atom, or 
       a cyano group; 
       
         
           
           
               
               
           
         
         wherein in the formula (32), 
         one or more pairs of two or more adjacent groups of R 331  to R 334  and R 341  to R 344  form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring; 
         R 331  to R 334  and R 341  to R 344  that do not form the substituted or unsubstituted, saturated or unsaturated ring, and R 351  and R 352  are independently 
       
       a hydrogen atom, 
       a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or 
       a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;
 R 361  to R 364  are independently 
 
       a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or 
       a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;
 wherein in the formulas (34-2) and (35-2), R 361  to R 364  are as defined in the formula (32); 
 one or more pairs of two or more adjacent groups of R 375  to R 377  and R 384  to R 386  form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring; 
 R 375  to R 377  and R 384  to R 386  that do not form the a substituted or unsubstituted, saturated or unsaturated ring, and R 387  are independently 
 
       a hydrogen atom, 
       a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or 
       a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. 
     
     
         2 . The organic electroluminescence device according to  claim 1 , wherein in the formula (1), at least two of R 1  to R 8  are deuterium atoms. 
     
     
         3 . The organic electroluminescence device according to  claim 1 , wherein in the formula (1), R 1  to R 8  are all deuterium atoms. 
     
     
         4 . The organic electroluminescence device according to  claim 1 , wherein in the formula (1), at least one hydrogen atom contained in one or more selected from a group consisting of L 1  and L 2  is a deuterium atom. 
     
     
         5 . The organic electroluminescence device according to  claim 1 , wherein in the formula (1), L 1  and L 2  are independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group. 
     
     
         6 . The organic electroluminescence device according to  claim 1 , wherein in the formula (1), at least one hydrogen atom contained in one or more selected from a group consisting of Ar 1  and Ar 2  is a deuterium atom. 
     
     
         7 . The organic electroluminescence device according to  claim 1 , wherein in the formula (1), Ar 1  and Ar 2  are independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted phenanthryl group. 
     
     
         8 . The organic electroluminescence device according to  claim 1 , wherein in the emitting layer, the content ratio of a compound having the same structure as formula (1) except that only protium atoms are contained as hydrogen atoms is 99 mol % or less. 
     
     
         9 - 11 . (canceled) 
     
     
         12 . The organic electroluminescence device according to  claim 1 , wherein one or more compounds selected from a group consisting of the following formulas (32), (34-2), and (35-2) is one or more compounds selected from a group consisting of the following formulas (32-11), (34-11) and (35-11): 
       
         
           
           
               
               
           
         
         wherein in the formulas (32-11), (34-11) and (35-11), 
         one or more pairs of two or more adjacent groups of R 3301  to R 3307  and R 3311  to R 3317  form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring: 
         R 3301  to R 3307  and R 3311  to R 3317  that do not form the substituted or unsubstituted, saturated or unsaturated ring, and R 3331  are independently
 a hydrogen atom, 
 a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or 
 a substituted or unsubstituted monovalent heterocyclic group having 5 to 20 ring atoms; 
 
         two R 3331 s may be the same with or different from each other, 
         R 3321  to R 3324  are independently
 a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or 
 a substituted or unsubstituted monovalent heterocyclic group having 5 to 20 ring atoms. 
 
       
     
     
         13 . The organic electroluminescence device according to  claim 12 , wherein the one or more compounds selected from the group consisting of the formulas (32-11), (34-11) and (35-11) is one or more compounds selected from a group consisting of the following formulas (32-12), (34-12) and (35-12): 
       
         
           
           
               
               
           
         
         wherein in the formulas (32-12), (34-12) and (35-12), R 3321  to R 3324  and R 3331  are as defined in the formulas (32-11), (34-11) and (35-11). 
       
     
     
         14 . The organic electroluminescence device according to  claim 12 , wherein R 3321  to R 3324  are independently a substituted or unsubstituted phenyl group. 
     
     
         15 . The organic electroluminescence device according to  claim 12 , wherein two R 3331 s are independently a hydrogen atom. 
     
     
         16 . The organic electroluminescence device according to  claim 12 , wherein the substituent in each case of “substituted or unsubstituted” is selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 ring carbon atoms, and a monovalent heterocyclic group having 5 to 20 ring atoms. 
     
     
         17 . The organic electroluminescence device according to  claim 12 , wherein the substituent in each case of “substituted or unsubstituted” is an alkyl group having 1 to 5 carbon atoms. 
     
     
         18 . The organic electroluminescence device according to  claim 12 , wherein R 3321  to R 3324  are independently a substituted or unsubstituted phenyl group, and two R 3331 s are independently a hydrogen atom. 
     
     
         19 . The organic electroluminescence device according to  claim 12 , wherein
 R 3321  to R 3324  are independently a substituted or unsubstituted phenyl group,   two R 3331 s are independently a hydrogen atom, and   the substituent in each case of “substituted or unsubstituted” is selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 ring carbon atoms, and a monovalent heterocyclic group having 5 to 20 ring atoms.   
     
     
         20 . The organic electroluminescence device according to  claim 12 , wherein
 R 3321  to R 3324  are independently a substituted or unsubstituted phenyl group,   two R 3331 s are independently a hydrogen atom, and   the substituent in each case of “substituted or unsubstituted” is an alkyl group having 1 to 5 carbon atoms.   
     
     
         21 . The organic electroluminescence device according to  claim 1 , wherein in the, one or more compounds selected from a group consisting of the following formulas (32), (34-2) and (35-2), one or more pairs of two or more adjacent groups of R 331  to R 334 , R 341  to R 344 , R 375  to R 377  and R 384  to R 386  form a substituted or unsubstituted, saturated or unsaturated ring. 
     
     
         22 - 27 . (canceled) 
     
     
         28 . The organic electroluminescence device according to  claim 1 , which further comprises a hole-transporting layer between the anode and the emitting layer. 
     
     
         29 . The organic electroluminescence device according to  claim 1 , which further comprises an electron-transporting layer between the cathode and the emitting layer. 
     
     
         30 . An electronic apparatus wherein the organic electroluminescence device according to  claim 1  is provided. 
     
     
         31 . The organic electroluminescence device according to  claim 1 , wherein in the compound represented by the formula (1), L 1  is a single bond, and Ar 1  is a substituted or unsubstituted 1-naphthyl group. 
     
     
         32 . The organic electroluminescence device according to  claim 1 , wherein in the compound represented by the formula (1), L 1  and L 2  are single bonds. 
     
     
         33 . The organic electroluminescence device according to  claim 1 , wherein in the compound represented by the formula (1), L 1  is a single bond, and Ar 1  is an unsubstituted phenyl group. 
     
     
         34 . The organic electroluminescence device according to  claim 1 , wherein in the compound represented by the formula (1), L 1  is a substituted or unsubstituted 1,4-naphthylene group, and Ar 1  is a substituted or unsubstituted phenyl group. 
     
     
         35 . The organic electroluminescence device according to  claim 1 , wherein in the formula (1), at least one of R 1  to R 8  is a deuterium atom, and hydrogen atoms contained in L 1 , L 2 , Ar 1  and Ar 2  are all protium atoms. 
     
     
         36 . The organic electroluminescence device according to  claim 1 , wherein the compound represented by the formula (1) is the compound represented by the following formula BH-1: 
       
         
           
           
               
               
           
         
       
     
     
         37 . The organic electroluminescence device according to  claim 1 , wherein the compound represented by the formula (1) is the compound represented by the following formula BH-2: 
       
         
           
           
               
               
           
         
       
     
     
         38 . The organic electroluminescence device according to  claim 1 , wherein the compound represented by the formula (1) is the compound represented by the following formula BH-3: 
       
         
           
           
               
               
           
         
       
     
     
         39 . The organic electroluminescence device according to  claim 1 , wherein the compound represented by the formula (1) is the compound represented by the following formula BH-4: 
       
         
           
           
               
               
           
         
       
     
     
         40 . The organic electroluminescence device according to  claim 1 , wherein the compound represented by the formula (1) is the compound represented by the following formula BH-5: 
       
         
           
           
               
               
           
         
       
     
     
         41 . The organic electroluminescence device according to  claim 1 , wherein the compound represented by the formula (1) is the compound represented by the following formula BH-6: 
       
         
           
           
               
               
           
         
       
     
     
         42 . The organic electroluminescence device according to  claim 1 , wherein the compound represented by the formula (1) is the compound represented by the following formula BH-7: 
       
         
           
           
               
               
           
         
       
     
     
         43 . The organic electroluminescence device according to  claim 1 , wherein the compound represented by the formula (1) is the compound represented by the following formula BH-8: 
       
         
           
           
               
               
           
         
       
     
     
         44 . The organic electroluminescence device according to  claim 1 , wherein the one or more compounds selected from a group consisting of the following formulas (32), (34-2) and (35-2) is one or more compounds selected from a group consisting of compounds represented by the following formulas BD-3 to BD-7: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         45 . The organic electroluminescence device according to  claim 1 , wherein the compound represented by the formula (1) is one or more compounds selected from a group consisting of compounds represented by the following formulas BH-1, BH-2, BH-7 and BH-8, and
 the one or more compounds selected from a group consisting of the following formulas (32), (34-2) and (35-2) is one or more compounds selected from a group consisting of compounds represented by the following formulas BD-3 to BD-7: