Compound derived from cyclopentadienone, preparation method thereof and EL element using the same

Abstract

Disclosed are a compound represented by the following formula (1), which is derived from cyclopentadienone and can be used as a core material for an organic electroluminescence element or other optical devices, and preparation method thereof, and an EL element using the same.

1 . A compound represented by the following formula (1):  
       
         
           
           
               
               
           
         
         wherein m is an integer of 0-5;  
         X is S, CR 1 R 2 , CR 1 ═CR 1 R 2 , C═NR 1  or C═NNR 1 R 2 ;  
         R 1 , R 2 , R 3 , R 1 ′, R 2 ′ and R 3 ′ may be the same with or different from each other, and are independently selected from the group consisting of hydrogen, C 1 -C 22  aliphatic alkyl group, C 1 -C 22  alicyclic alkyl and alkoxy group, and C 6 -C 18  aryl and aryloxy; and  
         Ar is an aromatic or heteroaromatic group selected from the group consisting of phenylene, naphthalene, anthracene, fluorene, thiophene, pyrrole, pyridine, aryloxadiazole, triazole, carbazole, arylamine, arylsilane and derivatives thereof.  
       
     
     
         2 . The compound according to  claim 1 , wherein R 1 , R 2 , R 3 , R 1 ′, R 2 ′ and R 3 ′ are independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, hexyl, ethylhexyl, heptyl, octyl, isooctyl, nonyl, decyl, dodecyl, hexadecyl, octadecyl, dococyl, cyclopropyl, cyclopentyl, cyclohexyl, methoxy, ethoxy, buthoxy, hexyloxy, methoxyethoxyethyl, methoxyethoxyethoxyethyl, cyanoethyl, carboxymethyl, phenyl, phenoxy, tolyl, benzyl, naphthyl, anthrancenyl and derivatives thereof.  
     
     
         3 . The compound according to  claim 1 , wherein Ar is selected from the group consisting of the substituents having the following structures:  
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein R 1 , R 2  and R 3  are independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, hexyl, ethylhexyl, heptyl, octyl, isooctyl, nonyl, decyl, dodecyl, hexadecyl, octadecyl, dococyl, cyclopropyl, cyclopentyl, cyclohexyl, methoxy, ethoxy, buthoxy, hexyloxy, methoxyethoxyethyl, methoxyethoxyethoxyethyl, cyanoethyl, carboxymethyl, phenyl, phenoxy, tolyl, benzyl, naphthyl, anthrancenyl and a derivative thereof.  
       
     
     
         4 . A preparation method of a compound represented by formula (1), using a compound of formula (3) or (4) as a starting material:  
       
         
           
           
               
               
           
         
         wherein m is an integer of 0-5;  
         X is S, CR 1 R 2 , CR 1 ═CR 1 R 2 , C═NR 1  or C═NNR 1 R 2 ;  
         R 1 , R 2 , R 3 , R 1 ′, R 2 ′, R 3 ′ and R 4  may be the same with or different from each other and are independently selected from the group consisting of hydrogen, C 1 -C 22  aliphatic alkyl group, C 1 -C 22  alicyclic alkyl and alkoxy group, and C 6 -C 18  aryl and aryloxy; and  
         Ar is an aromatic or heteroaromatic group selected from the group consisting of phenylene, naphthalene, anthracene, fluorene, thiophene, pyrrole, pyridine, aryloxadiazole, triazole, carbazole, arylamine, arylsilane and derivatives thereof.  
       
     
     
         5 . An EL element, comprising a compound according to  claim 1  in a light-emitting layer.  
     
     
         6 . The EL element according to  5 , in construction of anode/light-emitting layer/cathode, anode/hole transport layer/light-emitting layer/electron transport layer/cathode, or anode/electron injection layer/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode.