Compound for organic electric element, organic electric element comprising the same, and electronic device thereof

Abstract

Provided are a compound represented by Formula 24, an organic electric element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode and comprising the compound of Formula 24, and an electronic device thereof, the element and device having improved driving voltage, luminous efficiency and life time from the employment of the compound.

1 . A compound of Formula 24: 
       
         
           
           
               
               
           
         
         wherein Ar 4 , Ar 5 , Ar 10  and Ar 11  are each independently a C 6 -C 20  aryl group or a fluorenyl group, 
         L 5  is a C 12 -C 20  heterocyclic group containing at least one heteroatom selected from the group consisting of O and S, 
         wherein Ar 4 , Ar 5 , Ar 10 , Ar 11  and L 5  may be each optionally substituted with one or more substituents selected from the group consisting of deuterium, a C 1 -C 20  alkyl group, a C 6 -C 20  aryl group, and a C 6 -C 20  aryl group substituted with deuterium. 
       
     
     
         2 . The compound of  claim 1 , wherein L 5  is a dibenzofuran or dibenzothiophene group. 
     
     
         3 . The compound of  claim 1 , wherein Ar 4  and Ar 5  are each independently a C 6 -C 12  aryl group, and Ar 10  and Ar 11  are each independently a C 6 -C 12  aryl group or a fluorenyl group. 
     
     
         4 . The compound of  claim 1 , wherein Ar 4  and Ar 5  are each independently a phenyl or biphenyl group, and one of Ar 10  and Ar 11  is a phenyl or biphenyl group and the other is a 9,9-dimethyl-9H-fluorenyl group. 
     
     
         5 . The compound of  claim 4 , wherein Ar 4  and Ar 5  are each independently a phenyl group, Ar 10  is a biphenyl group, Ar 11  is a 9,9-dimethyl-9H-fluorenyl group. 
     
     
         6 . The compound of  claim 1 , wherein either Ar 10  or Ar 11  is a 2-(9,9-dimethyl-9H)-fluorenyl or 2-(9,9-diphenyl-9H)-fluorenyl group. 
     
     
         7 . The compound of  claim 1 , wherein the compound of Formula 24 is Compound 15-7 or Compound 15-8: 
       
         
           
           
               
               
           
         
       
     
     
         8 . An organic electric element comprising a first electrode, a second electrode and an organic material layer formed between the first and the second electrodes, wherein the organic material layer comprises the compound of Formula 24 of  claim 1 . 
     
     
         9 . The organic electric element of  claim 8 , wherein the organic material layer comprises a light emitting layer, and an emission-auxiliary layer formed between the light emitting layer and the first electrode, wherein the emission-auxiliary layer comprises the compound of Formula 24. 
     
     
         10 . The organic electric element of  claim 9 , wherein the organic material layer further comprises a hole transport layer formed between the light emitting layer and the first electrode, and the hole transport layer comprises a compound of Formula 21 or 22: 
       
         
           
           
               
               
           
         
         wherein: 
         Ar 4 , Ar 5  and Ar 9  are each independently selected from the group consisting of a C 6 -C 20  aryl group, a fluorenyl group, a C 2 -C 20  heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, C 3 -C 20  aliphatic ring, and a fused ring group formed by a C 3 -C 20  aliphatic ring with a C 6 -C 20  aromatic ring, of a C 1 -C 20  alkyl group, a C 2 -C 20  alkenyl group, a C 2 -C 20  alkynyl group, a C 1 -C 20  alkoxyl group, a C 6 -C 20  aryloxy group and -L′-N(R a )(R b ), 
         L 5  is selected from the group consisting of a C 6 -C 20  arylene group, a fluorenylene group, and a C 2 -C 20  heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 20  aliphatic ring and a fused ring group formed by a C 3 -C 20  aliphatic ring with a C 6 -C 20  aromatic ring, 
         L 6  is selected from the group consisting of a single bond, a C 6 -C 20  arylene group, a fluorenylene group, and a C 2 -C 20  heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 20  aliphatic ring and a fused ring group formed by a C 3 -C 20  aliphatic ring with a C 6 -C 20  aromatic ring, 
         R 6  to R 9  are each independently selected from the group consisting of hydrogen, deuterium, halogen, a C 6 -C 20  aryl group, a fluorenyl group, a C 2 -C 20  heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 20  aliphatic ring, a fused ring group formed by a C 3 -C 20  aliphatic ring with a C 6 -C 20  aromatic ring, a C 1 -C 20  alkyl group, a C 2 -C 20  alkenyl group, a C 2 -C 20  alkynyl group, a C 1 -C 20  alkoxyl group, a C 6 -C 20  aryloxy group and -L′-N(R a )(R b ), wherein adjacent groups may be linked to each other to form a ring, 
         h, i and g are each an integer of 0 to 4, j is an integer of 0 to 3, where each of these is an integer of 2 or more, a plurality of R 6 s, a plurality of R 7 s, a plurality of R 8 s, and a plurality of R 9 s are the same as or different from each other, 
         L′ is selected from the group consisting of a single bond, a C 6 -C 20  arylene group, a fluorenylene group, and a C 2 -C 20  heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 20  aliphatic ring, and a fused ring group formed by a C 3 -C 20  aliphatic ring with a C 6 -C 20  aromatic ring, 
         R a  and R b  are each independently selected from the group consisting of a C 6 -C 20  aryl group, a fluorenyl group, a C 2 -C 20  heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 20  aliphatic ring and a fused ring group formed by a C 3 -C 20  aliphatic ring with a C 6 -C 20  aromatic ring, 
         wherein Ar 4 , Ar 5 , Ar 9 , R 6  to R 9 , R a , R b , L 5 , L 6 , L′ and the ring formed by adjacent groups may be each optionally substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C 1 -C 20  alkyl group or a C 6 -C 20  aryl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a phosphine oxide group unsubstituted or substituted with a C 1 -C 20  alkyl group or a C 6 -C 20  aryl group, a C 1 -C 20  alkylthio group, a C 1 -C 20  alkoxyl group, a C 1 -C 20  alkyl group, a C 2 -C 20  alkenyl group, a C 2 -C 20  alkynyl group, a C 6 -C 20  aryl group, a C 6 -C 20  aryl group substituted with deuterium, a fluorenyl group, a C 2 -C 20  heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 20  cycloalkyl group, a fused ring group formed by a C 3 -C 20  aliphatic ring with a C 6 -C 20  aromatic ring, a C 7 -C 20  arylalkyl group, a C 8 -C 20  arylalkenyl group and a combination thereof. 
       
     
     
         11 . The organic electric element of  claim 9 , wherein the light emitting layer comprises a compound of Formula 12: 
       
         
           
           
               
               
           
         
         wherein: 
         Z 1  to Z 4 , Z 13  to Z 16  are independently C(R) or N, 
         Z 5  to Z 12  are independently C, C(R) or N, 
         L 2  is selected from the group consisting of a single bond, a C 6 -C 20  arylene group, a fluorenylene group, a C 2 -C 20  heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 20  aliphatic ring, and a fused ring group formed by a C 3 -C 20  aliphatic ring with a C 6 -C 20  aromatic ring, 
         W is N(Ar 5 ), N, O, S, C(R′) or C(R′)(R″), and W is N or C(R′) where W is combined with L 2 , 
         Ar 4  and Ar 5  are each independently selected from the group consisting of a C 6 -C 20  aryl group, a fluorenyl group, a C 2 -C 20  heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 20  aliphatic ring, a fused ring group formed by a C 3 -C 20  aliphatic ring with a C 6 -C 20  aromatic ring, a C 1 -C 20  alkyl group, a C 2 -C 20  alkenyl group, a C 2 -C 20  alkynyl group, a C 1 -C 20  alkoxyl group, a C 6 -C 20  aryloxy group, -L′-N(R a )(R b ) and a combination thereof, 
         R, R′ and R″ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a C 6 -C 20  aryl group, a fluorenyl group, a C 2 -C 20  heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 20  aliphatic ring, a fused ring group formed by a C 3 -C 20  aliphatic ring with a C 6 -C 20  aromatic ring, a C 1 -C 20  alkyl group, a C 2 -C 20  alkenyl group, a C 2 -C 20  alkynyl group, a C 1 -C 20  alkoxyl group, a C 6 -C 20  aryloxy group and -L′-N(R a )(R b ), wherein adjacent R groups may be optionally linked to each other to form a ring, and R′ and R″ may be optionally linked to each other to form a ring, 
         L′ is selected from the group consisting of a single bond, a C 6 -C 20  arylene group, a fluorenylene group, and a C 2 -C 20  heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 20  aliphatic ring, and a fused ring group formed by a C 3 -C 20  aliphatic ring with a C 6 -C 20  aromatic ring, and 
         R a  and R b  are each independently selected from the group consisting of a C 6 -C 20  aryl group, a fluorenyl group, a C 2 -C 20  heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 20  aliphatic ring, and a fused ring group formed by a C 3 -C 20  aliphatic ring with a C 6 -C 20  aromatic ring, 
         wherein L 2 , Ar 4 , Ar 5 , R, R′, R″, the ring formed by adjacent R, and the ring formed by R′ and R″ are each optionally substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C 1 -C 20  alkyl group or a C 6 -C 20  aryl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a phosphine oxide group unsubstituted or substituted with a C 1 -C 20  alkyl group or a C 6 -C 20  aryl group, a C 1 -C 20  alkylthio group, a C 1 -C 20  alkoxyl group, a C 1 -C 20  alkyl group, a C 2 -C 20  alkenyl group, a C 2 -C 20  alkynyl group, a C 6 -C 20  aryl group, a C 6 -C 20  aryl group substituted with deuterium, a fluorenyl group, a C 2 -C 20  heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 20  cycloalkyl group, a fused ring group formed by a C 3 -C 20  aliphatic ring with a C 6 -C 20  aromatic ring, a C 7 -C 20  arylalkyl group, a C 8 -C 20  arylalkenyl group and a combination thereof. 
       
     
     
         12 . An electronic device comprising a display device comprising the organic electric element of  claim 8 , and a control unit for driving the display device. 
     
     
         13 . The electronic device of  claim 12 , wherein the organic electric element is one of an organic light emitting diode, an organic solar cell, an organic photo conductor, an organic transistor, and an element for monochromatic or white illumination.