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KR-102963083-B1 - COMPOUND FOR ORGANIC ELECTRIC ELEMENT, ORGANIC ELECTRIC ELEMENT EMPLOYING THE SAME, AND AN ELECTRONIC DEVICE THEREOF

KR102963083B1KR 102963083 B1KR102963083 B1KR 102963083B1KR-102963083-B1

Abstract

The present invention discloses a compound represented by Formula 1, an organic electric device including the same, an electronic device including the same, and a method for recovering the same. By including the compound of Formula 1 in the organic layer of an organic electric device, the driving voltage of the organic electric device can be lowered and the luminous efficiency and lifespan can be improved.

Inventors

  • 이희채
  • 김유헌
  • 이중근

Assignees

  • 덕산네오룩스 주식회사

Dates

Publication Date
20260511
Application Date
20251114

Claims (13)

  1. Compound represented by the following chemical formula 1: <Chemical Formula 1><Chemical Formula A> In the above chemical formula 1, A is the chemical formula A, and Ar 1 to Ar 3 are independently selected from the group consisting of a C 6 to C 60 aryl group; a fluorenyl group; and a C 2 to C 60 heterocyclic group comprising at least one heteroatom among O and S, and Ar a is a C6 – C60 aryl group, and Ak is independently a C1 – C20 alkyl group or a C3 – C60 cycloalkyl group, and R1 and R2 are independently selected from the group consisting of hydrogen; deuterium; a C6 – C60 aryl group; a C2 – C60 heterocyclic group comprising at least one heteroatom among O and S; and a C1 – C20 alkyl group, and adjacent groups may bond to each other to form an aromatic ring, and R₃ is hydrogen or deuterium, and R' and R" are independently C1 – C20 alkyl groups or C6 – C60 aryl groups, and a is an integer from 0 to 2, b is an integer from 0 to 4, c is an integer from 0 to 4, and l is an integer from 1 to 3, and m, n, o, and p are each integers from 0 to 3, and at least one of m, n, o, and p is an integer greater than or equal to 1, and The aromatic ring formed by the bonding of the above aryl group, fluorenyl group, heterocyclic group, cycloalkyl group, alkyl group, and adjacent groups can each be substituted with one or more substituents selected from the group consisting of deuterium; C1 - C20 alkyl group; and C6 - C30 aryl group, and the hydrogen of the substituent can be replaced with deuterium.
  2. In Article 1, A compound in which the above Chemical Formula 1 is represented by one of the following Chemical Formulas 2-1 to 2-3: <Chemical Formula 2-1><Chemical Formula 2-2><Chemical Formula 2-3> In the above chemical formulas 2-1 to 2-3, A, Ar 1 to Ar 3 , Ak, R 3 , c, m, n, and o are as defined in claim 1.
  3. In Article 1, A compound in which the above chemical formula A is selected from the group consisting of the following chemical formulas A2-1 to A2-12: <Chemical Formula A2-1><Chemical Formula A2-2><Chemical Formula A2-3> <Chemical Formula A2-4><Chemical Formula A2-5><Chemical Formula A2-6> <Chemical Formula A2-7><Chemical Formula A2-8><Chemical Formula A2-9> <Chemical Formula A2-10><Chemical Formula A2-11><Chemical Formula A2-12> In the above chemical formulas A2-1 to A2-12, Ar a , Ak, R 1 , R 2 , R', R", a, b, and p are as defined in claim 1.
  4. In Article 1, The above Ak is a compound selected from the group consisting of the following chemical formulas Ak-1 to Ak-8: <Chemical Formula Ak-1><Chemical Formula Ak-2><Chemical Formula Ak-3><Chemical Formula Ak-4> <Chemical Formula Ak-5><Chemical Formula Ak-6><Chemical Formula Ak-7><Chemical Formula Ak-8> In the above chemical formulas Ak-1 to Ak-8, * indicates the bonding position, and hydrogen can be replaced with deuterium.
  5. In Article 1, A compound in which at least one of the above Ar 1 and Ar 2 is selected from the group consisting of the following Ar-1 to Ar-8: <Chemical Formula Ar-1><Chemical Formula Ar-2><Chemical Formula Ar-3><Chemical Formula Ar-4> <Chemical Formula Ar-5><Chemical Formula Ar-6><Chemical Formula Ar-7> Chemical formula Ar-8 In the above chemical formulas Ar-1 to Ar-8, W is O, S or C(R 13 )(R 14 ), and R4 to R9 , R13 and R14 are independently selected from the group consisting of hydrogen; deuterium; C1 - C20 alkyl groups; and C6 - C30 aryl groups, and d is an integer from 0 to 5, e and i are integers from 0 to 4, f is an integer from 0 to 7, g is an integer from 0 to 9, and h is an integer from 0 to 3.
  6. In Article 1, A compound in which at least one of m, n, and o is an integer of 2 or more.
  7. In an organic electric device comprising a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, The above organic layer is an organic electric device comprising the compound of claim 1.
  8. In Article 7, The above organic layer includes a light-emitting auxiliary layer, and the above light-emitting auxiliary layer includes the compound of claim 1, forming an organic electric device.
  9. In Article 7, An organic electric device characterized in that the above organic layer comprises two or more stacks including a hole transport layer, a light-emitting layer, and an electron transport layer sequentially formed on the first electrode.
  10. A display device comprising the organic electric element of claim 7; and An electronic device including a control unit for driving the above-mentioned display device.
  11. In Article 10, The above electronic device is characterized as being a wired or wireless communication terminal.
  12. In Paragraph 11, An electronic device characterized in that the above-mentioned wired/wireless communication terminal is a mobile communication terminal, navigation system, game console, TV, or computer.
  13. A step of depositing an organic layer material comprising a compound represented by Chemical Formula 1 of Claim 1; A step of recovering the organic layer material attached to the deposition equipment; and A method for recovering a compound characterized by including the step of purifying the recovered organic layer material to obtain a compound represented by Chemical Formula 1 having a purity of 99.9% or higher.

Description

Compound for organic electric element, organic electric element including the same, and an electronic device thereof The present invention relates to a compound for an organic electric device, an organic electric device including 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. The biggest issues regarding organic electroluminescent devices are lifespan and efficiency, and as displays become larger in size, these efficiency and lifespan issues must be resolved. Efficiency, lifespan, and driving voltage are interrelated; as efficiency increases, the driving voltage relatively decreases, and as the driving voltage drops, the crystallization of organic materials caused by Joule heating during operation is reduced, resulting in a tendency for increased lifespan. However, simply improving the organic layer does not maximize efficiency. This is because long lifespan and high efficiency can be achieved simultaneously when the energy levels and T1 values between each organic layer, as well as the intrinsic properties of the material (mobility, interfacial properties, etc.), form an optimal combination. Therefore, in order to fully realize the excellent characteristics of organic electronic devices, it is necessary to develop materials forming the organic layer within the device, particularly materials for the light-emitting auxiliary layer. FIGS. 1 to 3 are exemplary diagrams of an organic electroluminescent device according to an embodiment of the present invention. In this specification, "aryl group," "arylene group," and "aromatic ring" refer to hydrocarbon aromatic rings, and unless otherwise stated, each has 6 to 60 carbon atoms, but is not limited thereto. In the present invention, an aryl group or an arylene group includes a single ring, a polycyclic ring, and a condensed ring, etc. In addition, in this specification, the aryl group or arylene group is, for example, C6 ~ C60 , C6 ~ C30 , C6 ~ C29 , C6~ C28 , C6 ~ C27 , C6 ~ C26 , C6 ~ C25 , C6 ~ C24 , C6 ~ C23 , C6 ~C22, C6~ C21 , C6 ~ C20 , C6 ~ C19 , C6 ~ C18 , C6 ~ C17 , C6 ~ C16 , C6 ~ C15 , C6~ C14 , C6 ~C13 , C6 ~ C12 , C6 ~ C11 , C6 ~ C10 , C6 , C10 , It may be an aryl group or an arylene group such as C12 , C13 , C14 , C15 , C16 , C17 , C18 , and specifically, phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, benzophenanthrene, triphenylene, chrysene, or a combination thereof, in particular phenyl, naphthyl, phenanthrene, or a combination thereof. In this specification, "fluorenyl group" refers to a substituted or unsubstituted fluorenyl group, and "fluorenylene group" refers to a substituted or unsubstituted fluorenylene group. The fluorenyl group or fluorenylene group used in the present invention includes a spiro compound formed by R and R' being bonded to each other in the following structure, and also includes a compound in which adjacent R" are bonded to each other to form a ring. "Substituted fluorenyl group" and "substituted fluorenylene group" mean that at least one of R, R', and R" in the following structure is a substituent other than hydrogen, and in the chemical formula below, R" may be 1 to 8. In this specification, regardless of the valence, the fluorenyl group, fluorenylene group, etc. may be described as a fluoren group or fluorene. In addition, the fluorene group may be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, spiro[benzo[ b ]fluorene-11,9'-fluorene], benzo[ b ]fluorene, 11,11-diphenyl- 11H -benzo[ b ]fluorene, 9-(naphthalene-2-yl)9-phenyl- 9H -fluorene, etc. In addition, when one R" is substituted in the following chemical formula, depending on the position where R" is substituted, it can be 1-fluorene, 2-fluorene, 3-fluorene, or 4-fluorene, and when two R" are substituted, the two R" can be substituted at positions 2 and 5, 2 and 7, 4 and 5, 4 and 7, etc. In this specification, "spyro compound" refers to a compound having a "spyro linkage," where a spyro linkage means a connection formed by two rings sharing only one atom. At this time, the atom shared by the two rings is called a "spyro atom," and depending on the number of spyro atoms contained in a compound, they are respectively called "monospyro-," "diespyro-," and "trispyro-" compounds. For example, when R and R" in the above fluorene structural formula bond to each other to form a ring, a spiro compound may be formed, and the