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

Patent metadata

Field	Value
Publication number	US-11081649-B2
Application number	US-201716078733-A
Country	US
Kind code	B2
Filing date	Feb 13, 2017
Priority date	Feb 23, 2016
Publication date	Aug 3, 2021
Grant date	Aug 3, 2021

Abstract

Provided are a compound represented by Formula 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 and comprising the compound of Formula 1, and an electronic device comprising the element, where the driving voltage of the organic electronic device is lowered, and the luminous efficiency and life time of the organic electronic device is improved.

First claim

The invention claimed is:

1. A compound of Formula 1:

wherein:
X is O or S,
R 1 to R 4 are each independently selected from the group consisting of hydrogen, deuterium, 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 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 ), and neighboring R 1 groups, neighboring R 2 groups, neighboring R 3 groups, or neighboring R 4 groups are optionally linked to each other to form a ring,
a is an integer of 0 to 4, and b, c and d are each an integer of 0 to 3, and when each of a, b, c and d is an integer of 2 or more, each of the plurality of R 1 s to R 4 s may be the same or different from each other,
Ar 1 to Ar 3 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 heteroatom selected from the group consisting of O, N, S, Si, and 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 ), with the proviso that where Ar 1 is the heterocyclic group, Ar 1 is not C 8 -C 9 -heterocyclic group,
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 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 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 heteroatom selected from the group consisting of O, N, S, Si, and P, and
the above aryl group, fluorenyl group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxyl group, aryloxyl group, arylene group and fluorenylene group are each optionally further 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 alkoxyl 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 Formula 1 is represented by the following Formula 2 or 3:

wherein a, b, c, d, R 1 to R 4 , Ar 1 to Ar 3 are the same as defined in claim 1 .

3. The compound of claim 1 , wherein Formula 1 is represented by one of the following Formulas 4 to 9:

wherein X, a, b, c, d, R 1 to R 4 , Ar 1 to Ar 3 are the same as defined in claim 1 .

4. The compound of claim 1 , wherein Formula 1 is one of the following compounds:

5. 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 the compound of claim 1 .

6. The organic electric element of claim 5 , wherein the compound is comprised as a single compound or a mixture of two or more kinds in at least one layer of a hole injection layer, a hole transport layer, an emission-auxiliary layer, a light emitting layer, an electron transport layer, an electron transport auxiliary layer and an electron injection layer of the organic material layer.

7. The organic electric element of claim 5 further comprising a layer for improving luminous efficiency formed on at least one side of sides of the first electrode and the second electrode, wherein at least one side is not facing the organic material layer.

8. The organic electric element of claim 5 , wherein the organic material layer is formed by a process of spin coating, nozzle printing, inkjet printing, slot coating, dip coating or roll-to-roll.

9. An electronic device comprising a display device and a control unit for driving the display device, wherein the display device comprises the organic electric element of claim 5 .

10. The electronic device of claim 9 , wherein the organic electric element is an organic light emitting diode, an organic solar cell, an organic photo conductor, an organic transistor, or an element for monochromatic or white illumination.

Assignees

• Duk San Neolux Co Ltd

Inventors

• Lee Yun Suk
• Lee Sun-Hee
• So Kiho
• Park Hyoung Keun
• Park Jonggwang
• Jeong Yeonseok
• Park Junghwan
• Hwang Sunpil

Classifications

• H10K50/181

  Electron blocking layers · CPC title

• H10K85/655

  comprising only sulfur as heteroatom · CPC title

• C07D209/88 Primary

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title