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

Abstract

Provided is an organic electric element and an electronic device thereof, by using the mixture of the compounds as a phosphorescent host material, it is possible to achieve a high luminous efficiency and a low driving voltage of an organic electric element, and the life span of the device can be greatly improved.

1 .- 23 . (canceled) 
     
     
         24 . A compound represented by Formula 2 below 
       
         
           
           
               
               
           
         
         in Formula 2, 
         1) Ar 4  is selected from the group consisting of a C 6 -C 60  aryl group; a fluorenyl group; a C 2 -C 60  heterocyclic group including at least one hetero atom of O, N, S, Si and P; a fused ring group of a C 3 -C 60  aliphatic ring and a C 6 -C 60  aromatic ring; a C 1 -C 50  alkyl group; a C 2 -C 20  alkenyl group; a C 2 -C 20  alkynyl group; a C 1 -C 30  alkoxyl group; a C 6 -C 30  aryloxy group; and -L′-N(R a )(R b ) (where, L′ is selected from the group consisting of a single bond; a C 6 -C 60  arylene group; a fluorenylene group; a fused ring group of a C 3 -C 60  aliphatic ring and a C 6 -C 60  aromatic ring; and a C 2 -C 60  heterocyclic, and R a  and R b  are each independently selected from the group consisting of a C 6 -C 60  aryl group; a fluorenyl group; a fused ring group of a C 3 -C 60  aliphatic ring and a C 6 -C 60  aromatic ring; and a C 2 -C 60  heterocyclic group containing at least one hetero atom of O, N, S, Si, and P), 
         2) c and e are integer of 0 to 10, and d is an integer of 0 to 2, 
         3) R 3 , R 4  and R 5  may be the same or different, and are each independently selected from the group consisting of deuterium; halogen; a C 6 -C 60  aryl group; a fluorenyl group; a C 2 -C 60  heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C 3 -C 60  aliphatic ring and a C 6 -C 60  aromatic ring; a C 1 -C 50  alkyl group; a C 2 -C 20  alkenyl group; a C 2 -C 20  alkynyl group; a C 1 -C 30  alkoxyl group; a C 6 -C 30  aryloxy group; and -L′-N(R a )(R b ) wherein L′, Ra and Rb are same as defined above; or in case c and e are 2 or more and d is 2, R 3 , R 4  and R 5  are each in plural and are the same or different, and a plurality of R 1  or a plurality of R 2  or a plurality of R 3  or a plurality of R 4  or a plurality of R 5  may be bonded to each other to form a ring. 
         4) L 2  may be selected from the group consisting of a single bond, a C 6 -C 60  arylene group, and a fluorenylene group; a fused ring group of a C 3 -C 60  aliphatic ring and a C 6 -C 60  aromatic ring; and a C 2 -C 60  heterocyclic group, 
         5) A and B may be independently a C 6 -C 60  aryl group or a C 2 -C 20  heterocyclic group, wherein both A and B are a substituted or unsubstituted C 6  aryl group (phenyl group), d is 2 and R 4 s are bonded to each other to form a ring to form an aromatic or hetero ring, 
         6) i and j are independently 0 or 1, with the proviso that i+j is 1 or more, and when i or j is 0, it means a direct bond, 
         7) X 1  and X 2  are independently NR′, O, S, or CR′R″, wherein R′ and R″ are independently hydrogen; a C 6 -C 60  aryl group; a fluorenyl group; a C 3 -C 60  heterocyclic group; or a C 1 -C 50  alkyl group; or R′ and R″ may be bonded to each other to form a spiro, 
         wherein, the aryl group, fluorenyl group, arylene group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group may be substituted with one or more substituents selected from the group consisting of deuterium; halogen; a silane group substituted or unsubstituted with C 1 -C 20  alkyl group or C 6 -C 20  aryl group; siloxane group; boron group; germanium group; cyano group; nitro group; -L′-N(R a )(R b ); a C 1 -C 20  alkylthio group; C 1 -C 20  alkoxyl group; C 1 -C 20  alkyl group; C 2 -C 20  alkenyl group; C 2 -C 20  alkynyl group; C 6 -C 20  aryl group; C 6 -C 20  aryl group substituted with deuterium; a fluorenyl group; C 2 -C 20  heterocyclic group; C 3 -C 20  cycloalkyl group; C 7 -C 20  arylalkyl group and C 8 -C 20  arylalkenyl group, wherein the substituents may combine each other and form a saturated or unsaturated ring, wherein the term ‘ring’ means a C 3 -C 60  aliphatic ring or a C 6 -C 60  aromatic ring or a C 2 -C 60  heterocyclic ring or a fused ring formed by the combination thereof. 
       
     
     
         25 . 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, wherein the organic material layer comprises an emitting layer, wherein the emitting layer comprises a first host compound represented by Formula 1 as the phosphorescent light emitting layer and a second host compound represented by Formula 2.   
       
         
           
           
               
               
           
         
         In Formula 1 and Formula 2, 
         1) Ar 1 , Ar 2 , Ar 3 , and Ar 4  are each independently selected from the group consisting of a C 6 -C 60  aryl group; a fluorenyl group; a C 2 -C 60  heterocyclic group including at least one hetero atom of O, N, S, Si and P; a fused ring group of a C 3 -C 60  aliphatic ring and a C 6 -C 60  aromatic ring; a C 1 -C 50  alkyl group; a C 2 -C 20  alkenyl group; a C 2 -C 20  alkynyl group; a C 1 -C 30  alkoxyl group; a C 6 -C 30  aryloxy group; and -L′-N(R a )(R b ) wherein L′ is selected from the group consisting of a single bond; a C 6 -C 60  arylene group; a fluorenylene group; a fused ring group of a C 3 -C 60  aliphatic ring and a C 6 -C 60  aromatic ring; and a C 2 -C 60  heterocyclic, and R a  and R b  are independently selected from the group consisting of a C 6 -C 60  aryl group; a fluorenyl group; a fused ring group of a C 3 -C 60  aliphatic ring and a C 6 -C 60  aromatic ring; and a C 2 -C 60  heterocyclic group containing at least one hetero atom of P, N, S, Si, and P, wherein Ar 2  and Ar 3  may be bonded to each other to form a ring, 
         2) a is an integer of 0 to 4, and b is an integer of 0 to 3, and c and e are integer of 0 to 10, and d is an integer of 0 to 2, 
         3) R 1 , R 2 , R 3 , R 4  and R 5  may be the same or different, and are each independently selected from the group consisting of deuterium; halogen; a C 6 -C 60  aryl group; a fluorenyl group; a C 2 -C 60  heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C 3 -C 60  aliphatic ring and a C 6 -C 60  aromatic ring; a C 1 -C 50  alkyl group; a C 2 -C 20  alkenyl group; a C 2 -C 20  alkynyl group; a C 1 -C 30  alkoxyl group; a C 6 -C 30  aryloxy group; and -L′-N(R a )(R b ); or in case a, b, c, and e are 2 or more, d is 2, R 1 , R 2 , R 3 , R 4  and R 5  are each in plural and are the same or different, and a plurality of R 1  or a plurality of R 2  or a plurality of R 3  or a plurality of R 4  or a plurality of R 5  may be bonded to each other to form a ring. 
         4) L 1  and L 2  are each independently selected from the group consisting of a single bond, a C 6 -C 60  arylene group, and a fluorenylene group; a fused ring group of a C 3 -C 60  aliphatic ring and a C 6 -C 60  aromatic ring; and a C 2 -C 60  heterocyclic group, 
         5) A and B are each independently a C 6 -C 60  aryl group or a C 2 -C 20  heterocyclic group, wherein both A and B are a substituted or unsubstituted C 6  aryl group (phenyl group), d is 2, and R 4 s are bonded to each other to form an aromatic or hetero ring, 
         6) i and j are independently 0 or 1, with the proviso that i+j is 1 or more, and when i or j is 0, it means a direct bond, 
         7) X 1  and X 2  are independently NR′, O, S, or CR′R″, wherein R′ and R″ are independently hydrogen; a C 6 -C 60  aryl group; a fluorenyl group; a C 3 -C 60  heterocyclic group; or a C 1 -C 50  alkyl group, wherein R′ and R″ may be bonded to each other to form a spiro, 
         8) n is an integer of 1 or 2, and when n is 2, two Ar 2  are the same or different, and two Ar 3  are each the same or different. 
         wherein, the aryl group, fluorenyl group, arylene group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group may be substituted with one or more substituents selected from the group consisting of deuterium; halogen; a silane group substituted or unsubstituted with C 1 -C 20  alkyl group or C 6 -C 20  aryl group; siloxane group; boron group; germanium group; cyano group; nitro group; -L′-N(R a )(R b ); a C 1 -C 20  alkylthio group; C 1 -C 20  alkoxyl group; C 1 -C 20  alkyl group; C 2 -C 20  alkenyl group; C 2 -C 20  alkynyl group; C 6 -C 20  aryl group; C 6 -C 20  aryl group substituted with deuterium; a fluorenyl group; C 2 -C 20  heterocyclic group; C 3 -C 20  cycloalkyl group; C 7 -C 20  arylalkyl group and C 8 -C 20  arylalkenyl group, wherein the substituents may combine each other and form a saturated or unsaturated ring, wherein the term ‘ring’ means a C 3 -C 60  aliphatic ring or a C 6 -C 60  aromatic ring or a C 2 -C 60  heterocyclic ring or a fused ring formed by the combination thereof. 
       
     
     
         26 . The compound of  claim 25 , wherein the first host compound represented by Formula 1 comprises a compound represented by Formula 3 or Formula 4 below. 
       
         
           
           
               
               
           
         
         wherein R 1 , R 2 , L 1 , Ar 1 , Ar 2 , Ar 3 , a and b are the same as defined in  claim 25 . 
       
     
     
         27 . The compound of  claim 25 , wherein L 1  and L 2  are selected from the group consisting of the following Formulas (A-1) to (A-12): 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         In Formulas (A-1) to (A-12), 
         1) a′, c′, d′ and e′ are an integer of 0 to 4, and b′ is an integer of 0 to 5, and f′ and g′ are an integer of 0 to 3, and h′ is an integer of 0 to 1, 
         2) R 6 , R 7  and R 8  are the same or different, and are each independently selected from the group consisting of deuterium; halogen; a C 6 -C 60  aryl group; a fluorenyl group; a C 2 -C 60  heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C 3 -C 60  aliphatic ring and a C 6 -C 60  aromatic ring; a C 1 -C 50  alkyl group; a C 2 -C 20  alkenyl group; a C 2 -C 20  alkynyl group; a C 1 -C 30  alkoxyl group; a C 6 -C 30  aryloxy group; and -L′-N(R a )(R b ); 
         Or when e′, f′ and g′ are 2 or more, they are the same as or different from each other, and a plurality of R 6  or a plurality of R 7  or plurality of R 8  may be bonded to each other to form an aromatic or a heteroaromatic ring, or two adjacent R 6  and R 7 , or R 7  and R 8  may be bonded to form an aromatic or heteroaromatic ring, 
         3) Y is NR′, O, S or CR′R″ 
         4) R′ and R″ are the same as defined above, 
         5) Z 1 , Z 2  and Z 3  are independently of each other CR′ or N and at least one is N. 
       
     
     
         28 . The compound of  claim 25 , wherein the first host compound represented by Formula 1 is represented by any one of the following Formulas 5 to 8: 
       
         
           
           
               
               
           
         
         wherein 
         1) R 1 , R 2 , Ar 1 , Ar 2 , Ar 3 , a, b, R′ and R″ are the same as defined in  claim 25 , 
         2) R 6  and R 7  are the same or different, and are each independently selected from the group consisting of deuterium; halogen; a C 6 -C 60  aryl group; a fluorenyl group; a C 2 -C 60  heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C 3 -C 60  aliphatic ring and a C 6 -C 60  aromatic ring; a C 1 -C 50  alkyl group; a C 2 -C 20  alkenyl group; a C 2 -C 20  alkynyl group; a C 1 -C 30  alkoxyl group; a C 6 -C 30  aryloxy group; and -L′-N(R a )(R b ); or in case f′ and g′ are 2 or more, each as plurality are the same as or different from each other, and a plurality of R 6  or a plurality of R 7  or a plurality of R 8  or adjacent R 6  and R 7 , or adjacent R 7  and R 8  may be bonded to each other to form an aromatic or a heteroaromatic ring, 
         3) a′, c′ and d′ are each an integer of 0 to 4, and f′ and g′ are each an integer of 0 to 3, 
         4) Y is NR′, O, S or CR′R″. 
       
     
     
         29 . The compound of  claim 25 , wherein the first host compound represented by Formula 1 is represented by any one of Formulas 9 to 20 below: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein R 1 , R 2 , L 1 , Ar 1 , Ar 2 , Ar 3 , a and b are the same as defined in the  claim 25 . 
       
     
     
         30 . The compound of  claim 25 , wherein the first host compound represented by Formula 1 comprises a compound represented by any one of Formula 21 to Formula 22 below: 
       
         
           
           
               
               
           
         
         wherein R 1 , R 2 , L 1 , Ar 1 , Ar 2 , Ar 3 , a and b are the same as defined in the  claim 25 . 
       
     
     
         31 . The compound of  claim 25 , wherein n is 1 in Formula 1. 
     
     
         32 . The compound of  claim 25 , wherein n is 2 in Formula 2. 
     
     
         33 . The compound of  claim 25 , wherein the first host compound represented by Formula 1 comprises a compound represented by Formula 23 below: 
       
         
           
           
               
               
           
         
         wherein 
         1) R 1 , R 2 , L 1 , Ar 1 , Ar 2 , a, b and n are the same as defined in  claim 25 , 
         2) f is an integer of 0 to 3, and g is an integer of 0 to 4, 
         3) R 9  and R 10  are the same or different, and are each independently selected from the group consisting of deuterium; halogen; a C 6 -C 60  aryl group; a fluorenyl group; a C 2 -C 60  heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C 3 -C 60  aliphatic ring and a C 6 -C 60  aromatic ring; a C 1 -C 50  alkyl group; a C 2 -C 20  alkenyl group; a C 2 -C 20  alkynyl group; a C 1 -C 30  alkoxyl group; a C 6 -C 30  aryloxy group; and -L′-N(R a )(R b ); or in case f and g are 2 or more, each as plurality are the same as or different from each other, and a plurality of R 9  or a plurality of R 10  or adjacent R 9  and R 10  may be bonded to each other to form an aromatic or a heteroaromatic ring, 
         4) Y is NR′, O, S or CR′R″, 
         5) R′ and R″ are the same as defined above. 
       
     
     
         34 . The compound of  claim 25 , wherein the second host compound represented by the Formula 2 comprises a compound represented by Formula 24 or Formula 25 below: 
       
         
           
           
               
               
           
         
         wherein R 3 , R 4 , R 5 , Ar 4 , L 2 , c, d, e, A, B, X 1  and X 2  are the same as defined in the  claim 25 . 
       
     
     
         35 . The compound of  claim 25 , wherein A and B in the Formula 2 are selected from the group consisting of the following Formulas (B-1) to (B-7): 
       
         
           
           
               
               
           
         
         In Formulas (B-1) to (B-7), 
         1) Z 4  to Z 50  are CR′ or N, 
         2) R′ is the same as defined above, 
         3) * indicates the position to be condensed. 
       
     
     
         26 . The compound of  claim 25 , wherein R 4  in Formula 2 comprises a compound forming an aromatic ring or a heteroaromatic ring. 
     
     
         27 . The compound of  claim 25 , wherein the second host compound represented by Formula 2 comprises a compound represented by any one of the following Formulas 26 to 45: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         In Formulas 26 to 45, 
         Ar 4 , X 1 , X 2 , R 3 , R 4 , R 5 , L 2 , c, d, and e are the same as defined in the  claim 25 . 
       
     
     
         28 . The compound of  claim 25 , wherein the second host compound represented by Formula 2 comprises any one of compounds represented by Formulas 46 to 53 below: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         In Formulas 46 to 53, 
         R 3 , R 4 , R 5 , Ar 4 , L 2 , c, d, e, A, B, R′ and R″ are the same as defined in the  claim 25 . 
       
     
     
         29 . The compound of  claim 25 , wherein the first host compound represented by Formula 1 is any one of the following Compounds 1-1 to 1-68 and Compounds 2-1 to 2-68: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         30 . The compound of  claim 25 , wherein the second host compound represented by Formula 2 comprises any one of the following Compounds 3-1 to 3-86: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         31 . The compound of  claim 25 , wherein the emitting layer is a phosphorescent light emitting layer. 
     
     
         32 . The compound of  claim 25 , wherein the compounds represented by Formula 1 and by Formula 2 are mixed in a ratio of 1:9 to 9:1 to be included in the emitting layer. 
     
     
         33 . The compound of  claim 25 , wherein the compound represented by Formula 1 and by Formula 2 are mixed in a ratio of 1:9 to 5:5 to be included in the emitting layer. 
     
     
         34 . The compound of  claim 25 , wherein he compound represented by Formula 1 and by Formula 2 are mixed in a ratio of 2:8 or 3:7 to be included in the emitting layer. 
     
     
         35 . An electronic device comprising a display device including the organic electric element of  claim 25 ; and a control unit for driving the display device. 
     
     
         36 . The electronic device of  claim 35 , wherein the organic electric element is at least one of an OLED, an organic solar cell, an organic photo conductor, an organic transistor and an element for monochromic or white illumination.