Compound for organic electronic element, organic electronic element using same, and electronic device thereof
Provided are a mixture of compounds used as a phosphorescent host material in an organic electronic element, an organic electronic element comprising the compounds to achieve high light-emitting efficiency, low driving voltage, and significantly improved lifespan, and an electronic device comprising the element.
1. 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 and the emitting layer comprises a first host compound represented by Formula 1 and a second host compound represented by Formula 2:
wherein:
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 or P, a fused ring group of a C 3 -C 60 aliphatic ring with a C 6 -C 60 aromatic ring, and a C 1 -C 50 alkyl group, wherein Ar 2 and Ar 3 may combine 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 each independently an 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 are the same or different from each other, 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 with a C 6 -C 60 aromatic ring, a C 1 -C 60 alkyl group, a C 2 -C 20 alkenyl group, and a C 2 -C 20 alkynyl group; 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 being 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 5 may combine 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, a fluorenylene group, a fused ring group of a C 3 -C 60 aliphatic ring with 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,
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 combine to each other to form a spiro, and
8) n is an integer of 1 or 2, and when n is 2, two Ar 2 are the same or different from each other, and two Ar 3 are each the same or different from each other,
wherein the aryl group, fluorenyl group, heterocyclic group, fused ring group, and alkyl group of Ar 1 to Ar 4 and R 1 to R 5 , the alkenyl group of R 1 to R 5 , the arylene group, fluorenylene group, heterocyclic group, and fused ring group of L 1 and L 2 , the aryl group, fluorenyl group, heterocyclic group, and alkyl group of R′ and R″ may be substituted with one or more substituents selected from the group consisting of deuterium, halogen, 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, a C 3 -C 20 cycloalkyl group, a C 7 -C 20 arylalkyl group, and a 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.
2. The organic electric element according to claim 1 , wherein the first host compound represented by Formula 1 is represented by Formula 3 or 4:
wherein R 1 , R 2 , L 1 , Ar 1 , Ar 2 , Ar 3 , a and b are the same as defined in claim 1 .
3. The organic electric element according to claim 1 , wherein L 1 and L 2 are selected from the group consisting of the following Formulas (A-1) to (A-12):
wherein:
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 from each other, 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 with 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, and a C 6 -C 30 aryloxy group,
wherein when f′ and g′ are 2 or more, R 6 , R 7 and R 8 are each in plural being the same or different, and a plurality of R 6 or a plurality of R 7 or plurality of R 8 may combine to each other to form an aromatic or a heteroaromatic ring, and wherein two adjacent R 6 and R 7 , or R 7 and R 8 may combine 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 in claim 1 ,
5) Z 1 , Z 2 and Z 3 are independently of each other CR′ or N and at least one is N.
4. The organic electric element according to claim 1 , wherein the first host compound represented by Formula 1 is represented by any 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 1 ,
2) R 6 and R 7 are the same or different from each other, 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 with 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 -Cao alkoxyl group, and a C 6 -C 30 aryloxy group, or in case f′ and g′ are 2 or more, R 6 and R 7 are each in plural being the same or different, 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 combine 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, and
4) Y is NR′, O, S or CR′R″.
5. The organic electric element according to claim 1 , wherein the first host compound represented by Formula 1 is represented by any of the following Formulas 9 to 20:
wherein, R 1 , R 2 , L 1 , Ar 1 , Ar 2 , Ar 3 , a and b are the same as defined in claim 1 .
6. The organic electric element according to claim 1 , wherein the first host compound represented by Formula 1 comprises a compound represented by any of the following Formulas 21 to 22:
wherein R 1 , R 2 , L 1 , Ar 1 , Ar 2 , Ar 3 , a and b are the same as defined in claim 1 .
7. The organic electric element according to claim 1 , wherein n is 1 in Formula 1.
8. The organic electric element according to claim 1 , wherein n is 2 in Formula 1.
9. The organic electric element claim 1 , wherein the first host compound represented by Formula 1 comprises a compound represented by the following Formula 23:
wherein:
1) R 1 , R 2 , L 1 , Ar 1 , Ar 2 , a, b and n are the same as defined in claim 1 ,
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 from each other, 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 with 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, and a C 6 -C 30 aryloxy group; or in case f and g are 2 or more, R 9 and R 10 are each in plural being the same or different, and a plurality of R 9 or a plurality of R 10 or adjacent R 9 and R 10 may combine to each other to form an aromatic or a heteroaromatic ring,
4) Y is NR′, O, S or CR′R″, and
5) R′ and R″ are the same as defined in claim 1 .
10. The organic electric element according to claim 1 , wherein the second host compound represented by Formula 2 is represented by the following Formula 24 or 25,
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 claim 1 .
11. The organic electric element according to claim 1 , wherein A and B in Formula 2 are selected from the group consisting of the following Formulas (B-1) to (B-7):
wherein,
1) Z 4 to Z 50 are CR′ or N,
2) R′ is the same as defined in claim 1 ,
3) * indicates the position to be condensed.
12. The organic electric element according to claim 1 , wherein R 4 s in Formula 2 where d is 2, combine to each other to form an aromatic ring or a heteroaromatic ring.
13. The organic electric element according to claim 1 , wherein the second host compound represented by Formula 2 comprises a compound represented by any of the following Formulas 26 to 45:
wherein,
Ar 4 , X 1 , X 2 , R 3 , R 4 , R 5 , L 2 , c, d, and e are the same as defined in claim 1 .
14. The organic electric element according to claim 1 , wherein the second host compound represented by Formula 2 comprises any one of compounds represented by the following Formulas 46 to 53:
wherein,
R 3 , R 4 , R 5 , Ar 4 , L 2 , c, d, e, A, B, R′ and R″ are the same as defined in claim 1 .
15. The organic electric element according to claim 1 , wherein the first host compound represented by Formula 1 is one of the following Compounds 1-1 to 1-68 and Compounds 2-1 to 2-68:
16. The organic electric element according to claim 1 , wherein the second host compound represented by Formula 2 comprises one of the following Compounds 3-1 to 3-100:
17. The organic electric element according to claim 1 , wherein the emitting layer is a phosphorescent light emitting layer.
18. The organic electric element according to claim 1 , wherein the compounds represented by Formula 1 and 2 are mixed in a ratio of 1:9 to 9:1 to be included in the emitting layer.
19. The organic electric element according to claim 1 , wherein the compound represented by Formula 1 and 2 are mixed in a ratio of 1:9 to 5:5 to be included in the emitting layer.
20. The organic electric element according to claim 1 , wherein he compound represented by Formula 1 and 2 are mixed in a ratio of 2:8 or 3:7 to be included in the emitting layer.
21. An electronic device comprising a display apparatus comprising the organic electric element according to claim 1 ; and a driving part configured to drive the display apparatus.
22. The electronic device according to claim 21 , wherein the organic electric element is an OLED, an organic solar cell, an organic photo conductor, an organic transistor, or a device for monochromic or white illumination.