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

1. 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,

wherein the emitting layer is a phosphorescent emitting layer and comprises a first host compound represented by Formula 1 and a second host compound represented by Formula 4 or Formula 5:

wherein:

R 1 , R 2 and R 3 are the same or different from each other, and each independently hydrogen or deuterium,

R 4 and R 5 are each the same or different, and 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 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 3 -C 60 aliphatic 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 an adjacent plurality of R 4 or plurality of R 5 may be bonded to each other to form a ring,

X is O or S,

Ar 1 is 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; and a fused ring group of a C 3 -C 60 aliphatic ring and a C 6 -C 60 aromatic ring,

a is an integer from 0 to 7, b and e are each independently an integer from 0 to 4, c and d are each independently an integer from 0 to 3,

Ring B is an C 6 -C 20 aryl group,

Y 10 is O, S, CR 51 R 52 or NR 53 ,

Ar 12 , Ar 13 and Ar 14 are each independently selected from the group consisting of an 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; and a fused ring group of a C 3 -C 60 aliphatic ring and a C 6 -C 60 aromatic ring,

Ar 15 is each independently selected from the group consisting of an 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; and a fused ring group of a C 3 -C 60 aliphatic ring and a C 6 -C 60 aromatic ring; and -L″-NR f R g ,

L 12 , L 13 , L 14 , L 15 and L″ are each independently selected from the group consisting of 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; a C 2 -C 60 heterocyclic group including at least one heteroatom of O, N, S, Si or P,

R 31 and R 32 are each the same or different, and each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; nitro group; a C 6 -C 60 aryl group; 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; or an adjacent plurality of R 31 or a plurality of R 32 may be bonded to each other to form a ring,

R 51 , R 52 and R 53 are each independently selected from the group consisting of a C 6 -C 60 aryl group; 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 60 alkyl group; a C 2 -C 60 alkenyl group; a C 2 -C 60 alkynyl group; a C 1 -C 60 alkoxy group; and a C 6 -C 60 aryloxy group; or R 51 and R 52 may be bonded to each other to form a ring,

R f and R g are each independently selected from the group consisting of a C 6 -C 60 aryl group; fluorenyl group; a C 2 -C 60 heterocyclic group including at least one heteroatom of O, N, S, Si or P; and a C 3 -C 60 aliphatic ring,

ba and bb are each independently an integer from 0 to 4,

wherein the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxyl group and aryloxy group may be substituted with one or more substituents selected from the group consisting of deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C 1 -C 20 alkylthio group; C 1 -C 20 alkoxy 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; also the substituents may be bonded to each other to 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 group or a fused ring formed by the combination thereof.

2. The organic electronic element of claim 1 , wherein Ar 1 is represented by any one of Formulas (Ar-1) to (Ar-12):

wherein:

R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are the same as the definition of R 4 in claim 1 , or an adjacent plurality of R 6 , or plurality of R 7 , or plurality of R 8 , or plurality of R 9 , or plurality of R 10 , or plurality of R 11 , or plurality of R 12 may be bonded to each other to form a ring,

Y is O, S, CR 13 R 14 , NR 15 or SiR 16 R 17 , provided that when Y is bonded to Formula 1, it is -L 1 -N,

R 13 , R 14 , R 15 , R 16 and R 17 are each independently selected from the group consisting of hydrogen; deuterium; a C 1 -C 60 alkyl group; a C 6 -C 60 aryl group; and a C 2 -C 60 heterocyclic group including at least one hetero atom of O, N, S, Si or P; alternatively, R 13 and R 14 or R 16 and R 17 may be bonded to each other to form a spiro,

L 1 is each independently selected from the group consisting of 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; a C 2 -C 60 heteroarylene group including at least one heteroatom of O, N, S, Si or P;

f and j are each independently an integer from 0 to 5, g is an integer from 0 to 7, h is an integer from 0 to 9, i, k and l are an integer from 0 to 4, and

* means the position to be bonded.

3. The organic electronic element of claim 1 , wherein Formula 1 is represented by any one of compounds P-1 to P-107:

4. The organic electronic element of claim 1 , wherein Formula 4 is represented by any one of compounds H-1 to H-108:

5. The organic electronic element of claim 1 , wherein Formula 5 is represented by any one of compounds S-1 to S-108:

6. A compound represented by Formula 1:

wherein:

R 1 , R 2 and R 3 are each the same or different, and each independently hydrogen; or

deuterium, R 4 and R 5 are each the same or different, and 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 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 3 -C 60 aliphatic 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 an adjacent plurality of R 4 or plurality of R 5 may be bonded to each other to form a ring,

X is O or S,

Ar 1 is 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; and a fused ring group of a C 3 -C 60 aliphatic ring and a C 6 -C 60 aromatic ring,

a is an integer from 0 to 7, b and e are each independently an integer from 0 to 4, c and d are each independently an integer from 0 to 3,

wherein the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxyl group and aryloxy group may be substituted with one or more substituents selected from the group consisting of deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C 1 -C 20 alkylthio group; C 1 -C 20 alkoxy 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 1 -C 20 arylalkenyl group; also the substituents may be bonded to each other to 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 group or a fused ring formed by the combination thereof.

7. The compound of claim 6 , wherein Ar 1 is represented by any one of Formulas (Ar-1) to (Ar-12):

wherein:

R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are the same as the definition of R 4 in claim 6 , or an adjacent plurality of R 6 , or plurality of R 7 , or plurality of R 8 , or plurality of R 9 , or plurality of R 10 , or plurality of R 11 , or plurality of R 12 may be bonded to each other to form a ring,

Y is O, S, CR 13 R 14 , NR 15 or SiR 16 R 17 , provided that when Y is bonded to Formula 1, it is -L 1 -N,

R 13 , R 14 , R 15 , R 16 and R 17 are each independently selected from the group consisting of hydrogen; deuterium; a C 1 -C 60 alkyl group; a C 6 -C 60 aryl group; and a C 2 -C 60 heterocyclic group including at least one hetero atom of O, N, S, Si or P; alternatively, R 13 and R 14 or R 16 and R 17 may be bonded to each other to form a spiro,

L 1 is each independently selected from the group consisting of 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; a C 2 -C 60 heteroarylene group including at least one heteroatom of O, N, S, Si or P;

f and j are each independently an integer from 0 to 5, g is an integer from 0 to 7, h is an integer from 0 to 9, i, k and l are an integer from 0 to 4,

* means the position to be bonded.

8. The compound of claim 6 , wherein R 1 , R 2 and R 3 are deuterium.

9. The compound of claim 6 , wherein R 4 and R 5 are deuterium.

10. The compound of claim 6 , wherein Formula 1 is represented by any one of compounds P-1 to P-107:

11. A method for reusing the compound represented by Formula 1 according to claim 6 , comprising:

a step of depositing an organic light emitting material including the compound represented by Formula 1 in a manufacturing process of an organic light emitting device;

a step of removing impurities from the crude organic light emitting material recovered from the deposition apparatus;

a step of recovering the removed impurities; and

a step of purifying the recovered impurities to a purity of 99.9% or higher.

12. The organic electronic element of claim 1 , the organic electronic element further comprises a light efficiency enhancing layer formed on at least one surface of the first electrode and the second electrode, the surface being opposite to the organic material layer.

13. The organic electronic element of claim 1 , wherein the organic material layer comprises 2 or more stacks comprising a hole transport layer, an emitting layer, and an electron transport layer sequentially formed on the first electrode.

14. The organic electronic element of claim 13 , wherein the organic material layer further comprises a charge generation layer formed between the 2 or more stacks.

15. An electronic device comprising a display device comprising the organic electronic element of claim; and a control unit for driving the display device.

16. The electronic device according to claim 15 , wherein the organic electronic element is at least one of n OLED, an organic solar cell, an organic photo conductor(OPC), organic transistor (organic TFT) and an element for monochromic or white illumination.