Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
Provided are a compound of Formula 1 and an organic electric element including a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode and comprising the compound, the element showing improved luminous efficiency, stability, and life span.
1. A compound of Formula 1:
wherein,
L is
wherein * indicates the position to which the nitrogen atom (N) of the amine group in Formula 1 is linked,
Ar 1 to Ar 3 are each independently selected from the group consisting of a C 6 -C 60 aryl group; a fluorenylene group; a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P; a fused ring formed by 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 alkoxy group; a C 6 -C 30 aryloxy group; and combinations thereof,
a, b and m are each an integer of 0 to 4, and n is an integer of 0 to 3,
R 1 to R 4 are each independently selected from the group consisting of i) deuterium; tritium; halogen; a C 6 -C 60 aryl group; a fluorenyl group; a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P; a fused ring formed by 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 alkoxy group; a C 6 -C 30 aryloxy group; -L′-N(R a )(R b ); and combinations thereof, or ii) at least one of any two adjacent groups may be linked to form a ring and the group(s) of R′ to R 4 not forming a ring are the same as defined in i) above,
L′ is selected from the group consisting of a single bond; a C 6 -C 60 arylene group; a fluorenylene group; a fused ring formed by a C 3 -C 60 aliphatic ring and a C 6 -C 60 aromatic ring; a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P,
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 formed by 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 heteroatom selected from the group consisting of O, N, S, Si, and P,
each of the above aryl group, fluorenyl group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group and fluorenylene group may be substituted with one or more substituents selected from the group consisting of deuterium; halogen; a silane group; a siloxane group; a boron group; a germanium group; a cyano group; a nitro group; a C 1 -C 20 alkylthio group; a C 1 -C 20 alkoxy group; 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 containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P; a C 3 -C 20 cycloalkyl group; a C 7 -C 20 arylalkyl group; and a C 8 -C 20 arylalkenyl group.
2. The compound of claim 1 , wherein a and b are each O (zero), or R 3 and R 4 are each independently selected from the following structures:
3. The compound of claim 1 , wherein at least one of R 1 or R 2 is linked to form at least one ring between any two adjacent groups.
4. The compound of claim 3 represented by one of Formulas below:
wherein Ar 1 to Ar 3 , L, R 1 , R 2 , m and n are the same as defined in claim 1 .
5. The compound of claim 1 , wherein Ar 1 is selected from the following structures:
wherein X is O, S or C(R′)(R″),
R′ and R″ are each independently selected from the group consisting of hydrogen; deuterium; tritium; a C 6 -C 20 aryl group; a C 1 -C 20 alkyl group; and a C 2 -C 20 alkenyl group; or
R′ and R″ may be linked together to form a spiro compound with the carbon to which they are attached,
o is an integer of 0 to 4,
p is an integer of 0 to 3,
R 5 and R 6 are each independently selected from the group consisting of i) deuterium; tritium; halogen; a C 6 -C 60 aryl group; a fluorenyl group; a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P; 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 alkoxy group; a C 6 -C 30 aryloxy group; and combinations thereof, or ii) any two adjacent groups may be independently linked together to form at least one fused ring, and the other group(s) of R 5 to R 6 not forming a ring are the same as defined in i) above.
6. The compound of claim 5 ,
wherein Ar 1 is
and wherein Formula 1 is represented by one of Formulas 11 to 20 below:
in Formula 11 to Formula 20, Ar 2 , Ar 3 , L, R 1 , R 2 , m and n are the same as defined in claim 1 , and X, R 5 , R 6 , o and p are the same as defined in claim 5 .
7. The compound of claim 1 , wherein Ar 2 and Ar 3 are each independently selected from the following structures:
8. The compound of claim 1 , wherein Formula 1 is any one of the compounds below:
9. An organic electric element comprising a first electrode, a second electrode, and an organic material layer disposed between the first electrode and the second electrode, wherein the organic material layer comprises the compound of claim 1 .
10. The organic electric element of claim 9 , wherein the organic material layer comprises at least one of a hole injection layer, a hole transport layer, an emission-auxiliary layer and an emitting layer, and at least one of the layers comprises the compound in the same kind or two or more different kinds.
11. The organic electric element of claim 9 , wherein the organic electric element further comprises at least one layer to improve luminous efficiency, formed on at least one of the sides of the first and second electrodes opposite to the organic material layer.
12. The organic electric element of claim 9 , wherein the organic material layer is formed by any one of the processes of spin coating, nozzle printing, inkjet printing, slot coating, dip coating and roll-to-roll.
13. An electronic device comprising a display device, which comprises the organic electric element of claim 9 , and a control unit for driving the display device.
14. The electronic device of claim 13 , wherein the organic electric element comprises at least one of an organic light emitting diode (OLED), an organic solar cell, an organic photo conductor (OPC), an organic transistor (organic TFT), and an element for monochromatic or white illumination.