Compound for organic electric element, organic electric element using same, and electronic apparatus thereof
Provided are an organic electronic element comprising a light emitting layer composed of a mixture of compounds capable of improving luminous efficiency, stability, and lifespan of the element, and an electronic device therefor.
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 comprises a first host compound represented by Formula 1 and a second host compound represented by Formula 2 as a phosphorescent emitting layer:
wherein:
1) A and B rings are each independently a C 6 -C 20 aryl or C 2 -C 20 heterocycle group,
2) X 1 is S or O,
3) X 2 is N-L 7 -Ar 9 , O, S or CR′R″, wherein R′ and R″ are each independently hydrogen; a C 6 -C 60 aryl group; a fluorenyl group; or a C 1 -C 50 alkyl group, and R′ and R″ may be bonded to each other to form a spiro ring,
4) p and q are each an integer of 0-10, r is an integer of 0-3, s is an integer of 0-4,
5) R 1 , R 2 , R 3 and R 4 are each independently selected from the group consisting of hydrogen; 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 C 1 -C 50 alkyl group; a C 2 -C 20 alkenyl group; a C 2 -C 20 alkynyl group; and a C 1 -C 30 alkoxyl group;
6) Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 , Ar 7 , Ar 8 and Ar 9 are each independently selected from the group consisting of a C 6 -C 60 aryl group; a C 2 -C 60 heterocyclic group including at least one hetero atom of O, N, S, Si or P; a fluorenyl group; 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; and a C 2 -C 20 alkenyl group;
7) L 1 , L 2 , L 3 , L 4 , L 5 , L 5 , L 6 and L 7 are independently selected from the group consisting of a single bond; a C 6 -C 60 arylene group; a fluorenylene group; and a C 2 -C 60 heteroarylene group containing at least one hetero atom of O, N, S, Si or P,
wherein, the aryl group, fluorenyl group, arylene group, heterocyclic group, fluorenylene 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 cyano group; nitro 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; and C 3 -C 20 cycloalkyl group; wherein 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 A or B in Formula 1 is each independently selected from the group consisting of Formulas a-1 to a-7:
wherein:
Z 1 to Z 48 are each independently CR C or N,
Z 1 to Z 48 bonded to L 1 to L 7 are carbon (C),
R c is selected from the group consisting of a C 5 -C 50 aryl group; a fluorenyl group; a fused ring group of a C 3 -C 60 alophilic ring and a C 5 -C 50 aromatic ring, a C 2 -C 20 heterocyclic group including at least one hetero atom of O, N, S, Si or P,
* indicates the position to be condensed.
3. The organic electronic element of claim 1 , wherein L 1 , L 2 , L 3 , L 4 , L 5 L 6 and L 7 in Formula 1 or Formula 2 are represented by one of Formulas b-1 to b-13:
wherein:
Y is N-L 8 -Ar 10 , O, S or CR′R″,
L 8 is the same as the definition of L 1 in claim 1 ,
Ar 10 is as the same as the definition of Ar 1 in claim 1 ,
R′ and R″ are the same as defined in claim 1 ,
a, c, d and e are each independently an integer of 0 to 4, and b is an integer of 0 to 6, f and g are each independently an integer of 0 to 3, h is an integer of 0 to 2, i is an integer of 0 or 1,
R 5 , R 6 and R 7 are each independently hydrogen; deuterium; tritium; halogen; cyano group; nitro group; 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 a -N(R d )(R e );
or in case a, b, c, d, e, f and g are 2 or more, and h is 2 or more, R 5 , R 6 and R 7 are in plural being the same as or different, and a plurality of R 5 or a plurality of R 6 or a plurality of R 7 or adjacent R 5 and R 6 , or adjacent R 6 and R 7 may be bonded to each other to form an aromatic or a heteroaromatic ring,
wherein L a is selected from the group consisting of a single bond; a C 6 -C 60 arylene group; a fluorenylene group; a C 2 -C 60 heterocyclic group containing 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 3 -C 60 aromatic ring; and C 3 -C 60 aliphatic hydrocarbon group;
R d and R e 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 containing 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,
Z 49 , Z 50 , and Z 51 are each independently CR g or N,
at least one of Z 49 , Z 50 , and Z 51 is N,
R g is selected from the group consisting of hydrogen; deuterium; tritium; halogen; cyano group; nitro group; 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 adjacent R 5 and R g may be bonded to each other to form an aromatic or a heteroaromatic ring.
4. The organic electronic element of claim 1 , wherein at least one of Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 is represented by Formula 1-2:
wherein:
C and D are the same as the definition of A in claim 1 ,
X 3 is N-L 10 -Ar 11 , O, S or CR′R″,
L 9 and L 10 are the same as the definition of L 1 in claim 1 ,
Ar 11 is the same as the definition of Ar 1 in claim 1 ,
R′ and R″ are the same as defined in claim 1 .
5. The organic electronic element of claim 1 , wherein the first host compound represented by Formula 1 includes a compound represented by Formula 3 or Formula 4:
wherein:
Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 , L 1 , L 2 , L 3 , R 1 , R 2 are the same as defined in claim 1 ,
p′ is an integer of 0 to 3, and q′ is an integer of 0 to 2.
6. The organic electronic element of claim 1 , wherein the first host compound represented by Formula 1 includes a compound represented by any of Formulas 5 to 11:
wherein:
L 1 , L 2 , L 3 , Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 , R 1 , R 2 , X 1 are the same as defined in claim 1 ,
p′ is an integer of 0 to 3, and q′ is an integer of 0 to 2, o is an integer of 0 to 4.
7. The organic electronic element of claim 1 , wherein the first host compound represented by Formula 1 includes a compound represented by any of Formulas 12 to 21:
wherein:
Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 , L 1 , L 2 , L 3 , R 1 , R 2 , p, q, X 1 , A and B are the same as defined in claim 1 ,
p′ is an integer of 0 to 3, and q′ is an integer of 0 to 2.
8. The organic electronic element of claim 1 , wherein the compound represented by Formula 1 includes any of the following compounds:
9. The organic electronic element of claim 1 , wherein the second host compound represented by Formula 2 is represented by any of Formulas 22 to 25:
wherein:
X 2 , L 4 , L 5 , L 6 , Ar 7 , Ar 8 , R 3 , R 4 , r and s are the same as defined in claim 1 .
10. The organic electronic element of claim 1 , wherein the second host compound represented by Formula 2 includes a compound represented by Formula 26:
wherein:
X 2 , L 4 , L 5 , L 6 , Ar 7 , R 3 , R 4 , r and s are the same as defined in claim 1 ,
X 4 is the same as the definition of X 2 in claim 1 ,
R 8 and R 9 are the same as the definition of R 3 and R 4 in claim 1 ,
u is the same as the definition of r in claim 1 , and t is the same as the definition of s in claim 1 .
11. The organic electronic element of claim 1 , wherein the second host compound represented by Formula 2 includes a compound represented by any of Formulas 27 to 30:
wherein:
X 2 , L 4 , L 5 , L 6 , Ar 7 , R 3 , R 4 , r and s are the same as defined in claim 1 ,
X 4 is the same as the definition of X 2 in claim 1 ,
R 8 and R 9 are the same as definition of R 3 and R 4 in claim 1 ,
u is the same as the definition of r in claim 1 , and t is the same as the definition of s in claim 1 .
12. The organic electronic element of claim 1 , wherein the second host compound represented by Formula 2 includes any of the following compounds:
13. The organic electronic element of claim 1 comprising a hole transport layer, an emitting auxiliary layer, or both the layers between the first electrode and the emitting layer, wherein either of or both the layers include the compound of Formula 1.
14. The organic electronic element of claim 1 , wherein the compounds represented by Formula 1 and by Formula 2 are mixed in a ratio of 1:9 to 9:1 and are included in the emitting layer.
15. The organic electronic element of claim 1 , wherein the compounds represented by Formula 1 and by Formula 2 are mixed in a ratio of 1:9 to 5:5 and are included in the emitting layer.
16. The organic electronic element of claim 1 , wherein the compounds represented by Formula 1 and by Formula 2 are mixed in a ratio of 2:8 or 3:7 and are included in the emitting layer.
17. An electronic device comprising: a display device including the organic electric element of claim 1 ; and a control unit for driving the display device.
18. The compound of claim 17 , 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.