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US-20260130109-A1 - COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF

US20260130109A1US 20260130109 A1US20260130109 A1US 20260130109A1US-20260130109-A1

Abstract

Provided are a compound of Formula 1, a composition comprising the same, an organic electronic element using the same, and an electronic device thereof, wherein the compound can improve the luminous efficiency, stability, and lifespan of the element.

Inventors

  • Ji Su An
  • Se Hoon LEE
  • Hyun Ju Song
  • Hyun Ji OH

Assignees

  • DUK SAN NEOLUX CO., LTD.

Dates

Publication Date
20260507
Application Date
20251219
Priority Date
20201026

Claims (18)

  1. 1 . A compound represented by Formula 1: wherein: R 1 , R 2 and R 3 are each deuterium, R 4 is selected from the group consisting of deuterium; a C 6 -C 60 aryl group; a fluorenyl group; 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 alkoxy group; and a C 6 -C 30 an aryloxy group, and where R 4 is in plural, a plurality of R 4 may be the same or different from each other, and the adjacent groups thereof may be bonded to each other to form an aromatic ring, L 1 is a single bond; or a C 6 -C 12 arylene group, Ar 1 is a C 6 -C 12 aryl group, a and c are independently an integer of 0 to 6, b is an integer of 0 to 7, and d is an integer of 0 to 5, wherein the aryl group, arylene group, fluorenyl group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxyl group and aryloxy group may each be substituted with one or more substituents selected from the group consisting of deuterium; a C 1 -C 20 alkyl group; a C 1 -C 20 alkyl group substituted with deuterium; a C 6 -C 12 aryl group; and a C 6 -C 12 aryl group substituted with deuterium.
  2. 2 . The compound according to claim 1 , wherein the compound represented by Formula 1 is represented by any of Formulas 1-3 to 1-6: wherein: R 1 , R 2 , R 3 , R 4 , L 1 , Ar 1 , a, b, c and d are the same as defined in claim 1 .
  3. 3 . The compound according to claim 1 , wherein the compound represented by Formula 1 is represented by Formula 2-1 or Formula 2-2: wherein: R 1 , R 2 , R 3 , R 4 , L 1 , Ar 1 , a, b, c and d are the same as defined in claim 1 .
  4. 4 . The compound according to claim 1 , wherein Ar 1 of Formula 1 is represented by any of Formulas Ar-1 to Ar-3: wherein: R 6 and R 7 are independently the same or different from each other and are independently selected from the group consisting of deuterium; a C 1 -C 20 alkyl group; a C 1 -C 20 alkyl group substituted with deuterium; a C 6 -C 12 aryl group; and a C 6 -C 12 aryl group substituted with deuterium, and a plurality of adjacent groups thereof may be bonded to each other to form a ring, f is an integer from 0 to 5; g is an integer from 0 to 4; h is an integer from 0 to 7, and indicates the position to be bonded.
  5. 5 . The compound according to claim 1 , wherein L 1 of Formula 1 is represented by any one of Formulas L-1 to L-4: wherein: R 8 and R 9 are independently the same or different from each other and are independently selected from the group consisting of deuterium; a C 1 -C 20 alkyl group; a C 1 -C 20 alkyl group substituted with deuterium; a C 6 -C 12 aryl group; and a C 6 -C 12 aryl group substituted with deuterium, and a plurality of adjacent groups thereof may be bonded to each other to form a ring, i and j are independently an integer from 0 to 4; k is an integer from 0 to 5; l is an integer from 0 to 3; m is an integer from 0 to 6, and * indicates the position to be bonded.
  6. 6 . A composition for an organic electronic element comprising a first compound represented by Formula 1 of claim 1 ; and a second compound represented by Formula 4 or Formula 5: wherein: L 12 , L 13 , L 14 and L 15 are independently 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 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 12 , Ar 13 and Ar 14 are 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 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 3 -C 60 aliphatic ring; and -L′-N(R c )(R d ), Ar 15 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 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; and a C 3 -C 60 aliphatic ring, Y 10 is O, S, C(R 51 )(R 52 ) or NR 53 , Ring B is an C 6 -C 20 aryl, L′ 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 including at least one heteroatom of O, N, S, Si or P; and a C 3 -C 60 aliphatic ring, R 31 and R 32 are independently the same or different from each other and are independently selected from the group consisting of 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 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 alkoxy group; and a C 6 -C 30 aryloxy group, and a plurality of adjacent groups thereof may be bonded to each other to form a ring, R 51 , R 52 , R 53 , R c and R d are independently the same or different from each other and are 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 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 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 alkoxy group; and a C 6 -C 30 aryloxy group, and a plurality of adjacent groups thereof may be bonded to each other to form a spiro, ba and bb are 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, alkoxy group and aryloxy group may be substituted with one or more substituents selected from the group consisting of deuterium; halogen; silane group; silane group substituted with an C 6 -C 20 aryl group; siloxane group; boron group; 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; a C 3 -C 20 aliphatic ring; a C 7 -C 20 arylalkyl group; a C 8 -C 20 arylalkenyl group; and a C 7 -C 20 alkylaryl group; and -L′-N(R c )(R d ), and the hydrogen of these substituents may be substituted with one or more deuterium, and 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. 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 a compound according to claim 1 .
  8. 8 . The organic electronic element according to claim 7 , wherein the organic material layer comprises a hole transport area, an emitting layer and an electron transport area.
  9. 9 . The organic electronic element according to claim 7 , wherein the organic material layer is an emitting layer.
  10. 10 . The organic electronic element according to claim 7 , 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 a first electrode.
  11. 11 . The organic electronic element according to claim 10 , wherein the organic material layer further comprises a charge generation layer formed between the 2 or more stacks.
  12. 12 . The organic electronic element according to claim 7 , further comprising 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. 13 . An electronic device comprising a display device comprising the organic electronic element of claim 7 ; and a control unit for driving the display device.
  14. 14 . The electronic device according to claim 13 , wherein the organic electronic element is at least one of an OLED, an organic solar cell, an organic photo conductor (OPC), organic transistor (organic TFT) and an element for monochromic or white illumination.
  15. 15 . The electronic device according to claim 13 , wherein the electronic device is one of a wired communication terminal, wireless mobile communication terminal, PDAs, electronic dictionaries, PMPs, remote controls, navigation systems, game consoles, TVs, computers, watches, tablets, and virtual reality (VR) devices.
  16. 16 . 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 a composition for an organic electronic element of claim 6 .
  17. 17 . An electronic device comprising a display device comprising the organic electronic element of claim 16 ; and a control unit for driving the display device.
  18. 18 . A method for reusing the compound of Formula 1 of claim 1 comprising: recovering a crude organic light emitting material comprising a compound of Formula 1 from a deposition apparatus used in a process for depositing the organic emitting material to prepare an organic light emitting device; removing impurities from the crude organic light emitting material; recovering the organic light emitting material after the impurities are removed; and purifying the recovered organic light emitting material to have a purity of 99.9% or higher.

Description

BACKGROUND Technical Field The present invention relates to compounds for organic electronic elements, organic electronic elements using the same, and an electronic device thereof. Background Art In general, organic light emitting phenomenon refers to a phenomenon that converts electric energy into light energy by using an organic material. An organic electronic element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer interposed therebetween. Here, in order to increase the efficiency and stability of the organic electronic element, the organic material layer is often composed of a multi-layered structure composed of different materials, and for example, may include a hole injection layer, a hole transport layer, an emitting layer, an electron transport layer, an electron injection layer etc. A material used as an organic material layer in an organic electronic element may be classified into a light emitting material and a charge transport material, such as a hole injection material, a hole transport material, an electron transport material, an electron injection material etc. depending on its function. And the light emitting material can be classified into a high molecular weight type and a low molecular weight type according to the molecular weight, and it can be classified into a fluorescent material derived from a singlet excited state of an electron and a phosphorescent material derived from a triplet excited state of an electron depending on the light emission mechanism. Further, the light emitting material may be divided into blue, green, and red light emitting materials and yellow and orange light emitting materials necessary for realizing a better natural color according to the emission color. However, when only one material is used as a light emitting material, due to intermolecular interaction, the maximum emission wavelength shifts to a longer wavelength, and there are problems in that the color purity is lowered or the device efficiency is reduced due to the emission attenuation effect, therefore in order to increase color purity and increase luminescence efficiency through energy transfer, a host/dopant system may be used as a light emitting material. The principle is that when a small amount of a dopant having a smaller energy band gap than that of the host forming the emitting layer is mixed in the emitting layer, excitons generated in the emitting layer are transported to the dopant to emit light with high efficiency. Here, since the wavelength of the host moves to the wavelength band of the dopant, light having a desired wavelength can be obtained according to the type of dopant used. Currently, the portable display market is a large-area display, and the size thereof is increasing, and thus, more power consumption than the power consumption required for the existing portable display is required. Therefore, power consumption has become a very important factor for a portable display having a limited power supply such as a battery, and the problem of efficiency and lifetime must also be solved. Efficiency, lifespan, and driving voltage are interrelated. As efficiency increases, the driving voltage decreases relatively. As the driving voltage decreases, the crystallization of organic materials due to Joule heating generated during operation decreases, which results in a tendency for the lifespan to increase. However, the efficiency cannot be maximized simply by improving the organic material layer. This is because, when the energy level and T1 value between each organic material layer, and the intrinsic properties (mobility, interfacial properties, etc.) of materials are optimally combined, long lifetime and high efficiency can be achieved at the same time. Therefore, while delaying the penetration and diffusion of metal oxide from the anode electrode (ITO) into the organic layer, which is one of the causes of shortening the lifetime of the organic electronic element, it should have stable characteristics against Joule heating generated during device driving, and OLED devices are mainly formed by a deposition method, and it is necessary to develop a material that can withstand a long time during deposition, that is, a material with strong heat resistance. That is, in order to fully exhibit the excellent characteristics of an organic electronic element, it should be preceded that the material constituting the organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material. But the development of a stable and efficient organic material layer material for an organic electronic element has not yet been sufficiently made. Therefore, the development of new materials is continuously required, and in particular, the development of a host material