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KR-20260063912-A - COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF

KR20260063912AKR 20260063912 AKR20260063912 AKR 20260063912AKR-20260063912-A

Abstract

The present invention provides a novel compound capable of improving the luminous efficiency, stability, and lifespan of a device, an organic electric device using the same, and an electronic device thereof.

Inventors

  • 곽수진
  • 박지현
  • 이세훈
  • 이형동

Assignees

  • 덕산네오룩스 주식회사

Dates

Publication Date
20260507
Application Date
20241031

Claims (12)

  1. Compound represented by the following chemical formula 1 <Chemical Formula 1> <Chemical Formula 1-A> In the above chemical formula 1, X 1 and X 2 are independently O or S, and A is hydrogen; or deuterium; and, Ar is a C6 – C60 aryl group; a fluorenyl group; or a C2 – C60 heterocyclic group comprising at least one heteroatom among O, N, S, Si and P; and R1 , R2 , R3 , R4, R5 , R6 , R7, R8 , R9 , R10 , R11 , R12 , R13 , R14 , R15, R16 , R17 , R18 , R19 , and R20 are each identical or different and independently hydrogen; deuterium; an aryl group of C6 – C60 ; a fluorenyl group; a heterocyclic group of C2– C60 containing at least one heteroatom among O , N, S , Si, and P; an aliphatic ring of C3 – C60 ; an alkyl group of C1 – C50 ; an alkenyl group of C2 – C20 ; an alkyneyl group of C2 – C20 ; Selected from the group consisting of C1 – C30 alkoxyl groups; and C6 – C30 aryloxy groups; and However, any one of R8 , R9 , R10 , R11 , R12 , and R13 is a substituent represented by the above chemical formula 1-A, and Here, the aryl group, heterocyclic group, fluorenyl group, aliphatic cyclic group, and alkyl group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1 – C20 alkylthio group; C1 – C20 alkoxyl group; C1 – C20 alkyl group; C2 – C20 alkenyl group; C2 – C20 alkynyl group; C6 –C20 aryl group ; C6 – C20 aryl group substituted with deuterium; fluorenyl group; C2 – C20 heterocyclic group; C3 – C20 cycloalkyl group; C7 – C20 arylalkyl group; It may be further substituted with one or more substituents selected from the group consisting of C8 – C20 aryl alkenyl groups, and these substituents may also combine with each other to form a ring, wherein 'ring' refers to a fused ring composed of a C3 – C60 aliphatic ring, a C6 – C60 aromatic ring, a C2 – C60 heteroring, or a combination thereof, and includes saturated or unsaturated rings.
  2. A compound according to claim 1, characterized in that the above chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-6. <Chemical Formula 1-1><Chemical Formula 1-2> <Chemical Formula 1-3><Chemical Formula 1-4> <Chemical Formula 1-5><Chemical Formula 1-6> {In the above chemical formulas 1-1 to 1-6, X 1 , X 2 , A, Ar, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , and R 20 are identical to those defined in Claim 1.
  3. A compound according to claim 1, characterized in that Ar of Formula 1 is represented by any one of the following Formulas a-1 to a-15. <Chemical Formula a-1><Chemical Formula a-2><Chemical Formula a-3><Chemical Formula a-4> <Chemical Formula a-5><Chemical Formula a-6><Chemical Formula a-7><Chemical Formula a-8> <Chemical Formula a-9><Chemical Formula a-10><Chemical Formula a-11><Chemical Formula a-12> <Chemical Formula a-13><Chemical Formula a-14><Chemical Formula a-15> {In the above chemical formulas a-1 to a-15, R21 is selected from the group consisting of deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1 – C20 alkylthio group; C1 – C20 alkoxyl group; C1 – C20 alkyl group; C2 – C20 alkenyl group; C2 – C20 alkynyl group; C6 – C20 aryl group; deuterium-substituted C6 – C20 aryl group; fluorenyl group; C2 – C20 heterocyclic group; C3 – C20 cycloalkyl group; C7 – C20 arylalkyl group; and C8 – C20 arylalkenyl group; and P is NR';CR'R";O; or S; and R' and R" are independently selected from the group consisting of C1 – C20 alkyl groups; C2 – C20 alkenyl groups; C2 – C20 alkynyl groups; C6– C20 aryl groups; C6 – C20 aryl groups substituted with deuterium; fluorenyl groups; C2 – C20 heterocyclic groups; and C3 – C20 cycloalkyl groups; and l and m are independent integers from 0 to 5, n and p are integers from 0 to 7, and o is an integer from 0 to 9, and represents the part that binds to triazine.
  4. A compound according to claim 1, characterized in that the compound represented by the above chemical formula 1 is any one of the following compounds P-1 to P-80.
  5. A material for an organic electrical device comprising a compound represented by Chemical Formula 1 according to claim 1 and a compound represented by Chemical Formula 4 or Chemical Formula 5 below. Chemical formula 4 Chemical formula 5 In the above Chemical Formulas 4 and 5, L12 , L13 , L14 , and L15 are independently selected from the group consisting of single bonds; C6 – C60 arylene groups; fluorenylene groups; C2 – C60 heterocyclic groups comprising at least one heteroatom among O, N, S, Si, and P; and C3 – C60 aliphatic groups; and Ar 12 , Ar 13, and Ar 14 are independently selected from the group consisting of C 6 –C 60 aryl groups; fluorenyl groups; C 2 –C 60 heterocyclic groups comprising at least one heteroatom among O, N, S, Si, and P; and fused groups of C 3 –C 60 aliphatic rings and C 6 –C 60 aromatic rings, and 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 containing at least one heteroatom among O, N, S, Si, and P; a fused heterocyclic group of a C 3 –C 60 aliphatic ring and a C 6 –C 60 aromatic ring; and -L'-NR e R f ;, L' is selected from the group consisting of a single bond; a C6 – C60 arylene group; a fluorenylene group; a C2 – C60 heterocyclic group comprising at least one heteroatom among O, N, S, Si and P; and a C3 – C60 aliphatic group; and R e and R f are independently selected from the group consisting of C 6 –C 60 aryl groups; fluorenyl groups; C 2 –C 60 heterocyclic groups containing at least one heteroatom among O, N, S, Si and P; and C 3 –C 60 aliphatic groups, and Y 10 is O, S, NR 53 or CR 51 R 52 and, The B ring is an aryl group of C6 – C20 , and R31 and R32 are each identical or different and are independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; nitro group; C6 – C60 aryl group; fluorenyl group; C2 – C60 heterocyclic group comprising at least one heteroatom among O, N, S, Si and P; fused ring of a C3 – C60 aliphatic ring and a C6 – C60 aromatic ring; C1 – C60 alkyl group; C2 – C60 alkenyl group; C2 – C60 alkynyl group; C1 – C60 alkoxy group; and C6 – C60 aryloxy group; or adjacent plurality of R13s or plurality of R14s may bond to each other to form a ring, R51 , R52 , and R53 are independently selected from the group consisting of a C6 – C60 aryl group; a fluorenyl group; a C2 – C60 heterocyclic group comprising at least one heteroatom among O, N, S, Si, and P; a fused ring of a C3 – C60 aliphatic ring and a C6 – C60 aromatic ring; a C1 – C60 alkyl group; a C2 – C60 alkenyl group; a C2 – C60 alkynyl group; a C1 – C60 alkoxy group; and a C6 – C60 aryloxy group; or R' and R" can be bonded to each other to form a spiro ring, and ba and bb are independent integers from 0 to 4, and Here, the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenyllene group, aliphatic circular group, fused circular group, alkyl group, alkenyl group, alkyneyl group, alkoxyl group, and aryloxy group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1 – C20 alkylthio group; C1 – C20 alkoxy group; C1 – C20 alkyl group; C2 – C20 alkenyl group; C2 – C20 alkyneyl group; C6 – C20 aryl group; C6 – C20 aryl group substituted with deuterium; fluorenyl group; C2 – C20 heterocyclic group; It may be further substituted with one or more substituents selected from the group consisting of C3 – C20 cycloalkyl groups; C7 – C20 arylalkyl groups; and C8 – C20 arylalkenyl groups; and these substituents may also bond to each other to form a ring, wherein 'ring' refers to a fused ring composed of a C3 – C60 aliphatic ring, a C6 – C60 aromatic ring, a C2 – C60 heteroring, or a combination thereof, and includes saturated or unsaturated rings.
  6. An organic electric device comprising a first electrode; a second electrode and an organic layer between the first electrode and the second electrode, wherein the organic layer comprises a compound according to claim 1 or a material for an organic electric device according to claim 5.
  7. In claim 6, an organic electric device further comprising a light efficiency improving layer formed on at least one surface of the first electrode and the second electrode opposite to the organic layer.
  8. An organic electric device according to claim 6, wherein the organic layer comprises two or more stacks including a hole transport layer, a light-emitting layer, and an electron transport layer sequentially formed on a first electrode.
  9. An organic electric device according to claim 8, wherein the organic layer further comprises a charge generating layer formed between the two or more stacks.
  10. An electronic device comprising: a display device including an organic electric element of claim 6; and a control unit for driving the display device.
  11. An electronic device according to claim 10, wherein the organic electric device is at least one of an organic electroluminescent device, an organic solar cell, an organic photosensitive material, an organic transistor, and a monochromatic or white lighting device.
  12. A step of depositing an organic light-emitting material comprising a compound represented by Chemical Formula 1 of Claim 1 in a manufacturing process of an organic light-emitting device; A step of removing impurities from an unpurified organic light-emitting material recovered from a deposition apparatus; A step of recovering the removed impurities; and A method for reusing a compound represented by Formula 1 according to claim 1, comprising the step of purifying the recovered impurities to a purity of 99.9% or higher.

Description

Compound for organic electric elements, organic electric element using the same, and electronic device thereof {COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF} The present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device thereof. In general, organic light emission refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic electrical devices utilizing organic light emission typically have a structure that includes an anode, a cathode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure made of different materials to increase the efficiency and stability of the organic electrical device, and may consist of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. Materials used as organic layers in organic electronic devices can be classified according to their function into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials. Furthermore, the light-emitting materials can be classified into high-molecular and low-molecular types based on molecular weight, and into fluorescent materials derived from the singlet excited state of electrons and phosphorescent materials derived from the triplet excited state of electrons based on the light emission mechanism. Additionally, light-emitting materials can be classified according to their emission color into blue, green, and red light-emitting materials, as well as yellow and orange light-emitting materials necessary to achieve better natural colors. Meanwhile, when only a single material is used as a light-emitting material, intermolecular interactions cause the maximum emission wavelength to shift to a longer wavelength, resulting in reduced color purity or decreased device efficiency due to light attenuation effects. Therefore, a host/dopant system can be used as a light-emitting material to increase color purity and luminous efficiency through energy transfer. The principle is that when a small amount of a dopant, which has a smaller energy band gap than the host forming the light-emitting layer, is mixed into the light-emitting layer, excitons generated in the light-emitting layer are transported to the dopant, emitting high-efficiency light. At this time, since the wavelength of the host shifts to the wavelength range of the dopant, light of the desired wavelength can be obtained depending on the type of dopant used. Currently, the portable display market is trending toward larger displays, which requires higher power consumption than that of conventional portable displays. Consequently, for portable displays that rely on the limited power source of batteries, power consumption has become a critical factor, and issues regarding efficiency and lifespan must also be resolved. Efficiency, lifespan, and driving voltage are interrelated; as efficiency increases, the driving voltage relatively decreases. Consequently, a lower driving voltage reduces the crystallization of organic materials caused by Joule heating during operation, which tends to extend the lifespan. However, simply improving the organic layers does not guarantee maximum efficiency. This is because both a long lifespan and high efficiency can be achieved simultaneously when the energy levels and T1 values between the organic layers, along with the intrinsic properties of the materials (mobility, interfacial characteristics, etc.), form an optimal combination. Therefore, it is necessary to delay the penetration and diffusion of metal oxides from the anode electrode (ITO) into the organic layer, which is one of the causes of shortened lifespan in organic electrical devices, while possessing stable characteristics against Joule heating generated during device operation. Furthermore, since OLED devices are primarily formed by deposition methods, there is a need to develop materials that can withstand the deposition process for a long time—that is, materials with strong heat resistance. In other words, to fully realize the excellent characteristics of organic electronic devices, it is essential that the materials forming the organic layer within the device—such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electron injection materials—be supported by stable and efficient materials. However, the development of stable and efficient organic layer materials for organic electronic devices has not yet been sufficiently achieved. Consequently, the development of new materials continues to be required, and among these, the development of host materials for the light-emitting layer is pa