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

1. A compound represented by Formula (1) below:

wherein,

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 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 ) 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 the 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 O, N, S, Si, or P,

2) c is an of 0 to 6, and d and e are integer of 0 to 4,

3) 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 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 c, d and e are each an integer of 2 or more, R 3 , R 4 and R 5 are each in plural being the same or different and a plurality of R 3 s or a plurality of R 4 s or a plurality of R 5 s may combine to each other to form a ring,

4) L 2 is 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 and a C 6 -C 60 aromatic ring; and a C 2 -C 60 heterocyclic group,

5) X 1 is O or S,

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 ) wherein L′, R a and R b are the same as defined above; 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, and also, these substituents may combine each other and form a ring, wherein the term ‘ring’ means C 3 -C 60 aliphatic ring or C 6 -C 60 aromatic ring or a C 2 -C 60 heterocyclic ring or a fused ring formed by the combination of them, and includes a saturated or unsaturated ring.

2. The compound according to claim 1 , wherein the compound represented by Formula (1) is a compound represented by the following Formula (2):

wherein,

1) R 3 , R 4 , R 5 , L 2 , c, d, e and X 1 are the same as defined in claim 1 ,

2) Z 1 , Z 2 , and Z 3 are each independently selected from the group consisting of CR 0 or N, and R 0 is each independently selected from the group consisting of hydrogen; deuterium; 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′, R a and R b are the same as defined in claim 1 ;

3) z is an integer of 0 to 2,

4) R 11 being the same or different from each other when z is 2, is 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′, R a and R b are the same as defined in claim 1 ; or R 11 may combine with R 0 of Z or adjacent R 11 when z is 2 to form an aromatic or heteroaromatic ring.

3. The compound according to claim 2 , wherein at least one of Z 1 , Z 2 and Z 3 in Formula (2) is N.

4. The compound according to claim 1 , wherein the compound represented by Formula (1) is represented by any of the following Formulas (3) to (7):

wherein,

1) R 3 , R 4 , R 5 , L 2 , c, d, e and X 1 are the same as defined in claim 1 ,

2) z is an integer of 0 to 2,

3) R 1 being the same or different from each other when z is 2, is 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′, R a and R b are the same as defined in claim 1 ; or R 11 may combine with R 0 of Z or adjacent R 11 when z is 2 to form an aromatic or heteroaromatic ring.

5. The compound according to claim 1 , wherein the compound represented by Formula (1) is represented by any of the following Formulas (8) to (19);

wherein

1) R 3 , R 4 , R 5 , L 2 , c, d, e and X are the same as defined in claim 1 ,

2) Z 1 , Z 2 , and Z 3 are each independently selected from the group consisting of CR 0 or N, and R 0 is each independently selected from the group consisting of hydrogen; deuterium; 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′, R a and R b are the same as defined in claim 1 ;

3) Ar 5 and Ar 6 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′, R a and R b are the same as defined in claim 1 ,

4) Y 1 and Y 2 are each independently NR′, O, S or CR′R″, and R′ and R″ are each 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 with each other to form a ring with a spiro.

6. The compound according to claim 5 , wherein at least one of Z 1 , Z 2 and Z 3 in any one of Formulas (8) to (19) is N.

7. An organic electronic 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 the following Formula (20) and a second host compound represented by the following Formula (1) as a phosphorescent light emitting layer:

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 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 the 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 O, N, S, Si, or P, and 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 is an integer of 0 to 6, and d is an integer of 0 to 4, and e is an integer of 0 to 4;

3) R 1 , R 2 , R 3 , R 4 and R 5 being the same or different from each other 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′, R a and R b are the same as defined above; or in case a, b, c, and e are an integer of 2 or more and 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 s or a plurality of R 2 s or a plurality of R 3 s or a plurality of R 4 s or a plurality of R 5 s may combine to each other to form a ring;

4) L 1 and L 2 are 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 and a C 6 -C 60 aromatic ring; and a C 2 -C 60 heterocyclic group,

6) X1 is O or S,

7) n is an integer of 1 or 2, and when n is 2 each of the two Ar 2 and the two Ar 3 are the same or different from each other,

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 ) wherein L′, R a and R b are the same as defined above; 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, and also, these substituents may combine each other and form a ring, wherein the term ‘ring’ means C 3 -C 60 aliphatic ring or C 6 -C 60 aromatic ring or a C 2 -C 60 heterocyclic ring or a fused ring formed by the combination of them, and includes a saturated or unsaturated ring.

8. The compound according to claim 7 , wherein the compound represented by Formula (20) is represented by the following Formula (21) or Formula (22):

wherein R 1 , R 2 , L 1 , Ar 1 , Ar 2 , Ar 3 , a and b are the same as defined in claim 7 .

9. The compound according to claim 7 , wherein L 1 and L 2 in Formulas (1) and (20) are selected from the group consisting of the following formulas (A-1) to (A-12):

wherein,

1) a′, c′, d′ and e′ are each an integer of 0 to 4; b′ is an integer of 0 to 6; f′ and g′ are each 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 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′, R a and R b are the same as defined in claim 7 ; or

when f′ and g′ are an integer of 2 or more, a plurality of R 6 s or a plurality of R 7 s or a plurality of R 8 s being the same or different from each other, may combine 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 combine to form an aromatic or heteroaromatic ring,

3) Y is NR′, O, S or CR′R″, and R′ and R″ are each 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 with each other to form a ring with a spiro,

4) Z 4 , Z 5 and Z 6 are independently of each other CR′ or N and at least one is N.

10. The compound according to claim 9 , wherein the compound represented by Formula (20) is represented by any of the following Formulas (23) to (26):

wherein,

1) R 1 , R 2 , L 1 , Ar 1 , Ar 2 , Ar 3 , a and b are the same as defined in claim 7 , and

2) R 6 , R 7 , c′, d′, f′, g′ and Y are the same as defined in claim 9 .

11. The compound according to claim 7 , wherein the compound represented by Formula (20) is represented by any of the following Formulas (27) to (38):

wherein R 1 , R 2 , L 1 , Ar 1 , Ar 2 , Ar 3 , a and b are the same as defined in claim 7 .

12. The compound according to claim 7 , wherein the compound represented by Formula (20) is represented by the following Formula (39) or Formula (40):

wherein R 1 , R 2 , L, Ar 1 , Ar 2 , Ar 3 , a and b are the same as defined in claim 7 .

13. The organic electronic element according to claim 7 , wherein n is 1 in Formula (20).

14. The organic electronic element according to claim 7 , wherein n is 2 in Formula (20).

15. The organic electronic element according to claim 7 , wherein the compound represented by Formula (20) is represented by the following Formula (41):

wherein 1) R 1 , R 2 , L, Ar 1 , Ar 2 , Ar 3 , a and b are the same as defined above,

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 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′, R a and R b are the same as defined in claim 7 ; or in case f and g are an integer of 2 or more, a plurality of R 9 s or a plurality of R 10 s being the same or different from each other, 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″,

5) R′ and R″ are each 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 ring with a spiro.

16. The compound according to claim 1 , wherein the compound represented by Formula (1) is represented by the following Formulas 3-1 to 3-92 and Formulas 4-1 to 4-92:

17. The organic electronic element according to claim 7 , wherein the compound represented by Formula (20) is represented by the following Formulas 1-1 to 1-68 and Formulas 2-1 to 2-68

18. The compound according to claim 1 , wherein the compound represented by Formula (1) is used as a phosphorescent host.

19. The compound according to claim 1 , wherein the compound represented by Formula (1) is used as a red phosphorescent host.

20. The organic electronic element of claim 7 , further comprising at least one hole transporting band layer between the first electrode and the emitting layer, wherein the hole transporting band layer includes a hole transport layer, an emitting auxiliary layer, or both, and the hole transporting band layer includes a compound represented by Formula (20).

21. The organic electronic element of claim 7 , wherein a ratio of the compound represented by Formula (1) to the compound represented by Formula (20) is 1:9 to 9:1 to be used in the emitting layer.

22. The organic electronic element of claim 20 , wherein a ratio of the compound represented by Formula (1) to the compound represented by Formula (20) is 5:5 to 9:1 to be used in the emitting layer.

23. A display device comprising the organic electronic element of claim 7 ; and a control part driving the display device.

24. A display device according to claim 23 , wherein the organic electronic element is an OLED, an organic solar cell, an organic photo conductor (OPC), organic transistor (organic TFT), or an element for monochromic or white illumination.