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KR-102963534-B1 - Novel boron compounds and organic light emitting diode including the same

KR102963534B1KR 102963534 B1KR102963534 B1KR 102963534B1KR-102963534-B1

Abstract

The present invention relates to a boron compound usable in an organic light-emitting diode and an organic light-emitting diode comprising the same, and more specifically, to a boron compound represented by [Chemical Formula A-1] to [Chemical Formula A-6] and an organic light-emitting diode comprising the same, wherein [Chemical Formula A-1] to [Chemical Formula A-6] are identical to those described in the detailed description of the invention.

Inventors

  • 주성훈
  • 박경화
  • 신봉기
  • 김지환
  • 조현준
  • 최성은
  • 우성은
  • 박동명
  • 문준영
  • 강수경

Assignees

  • 에스에프씨 주식회사

Dates

Publication Date
20260513
Application Date
20210408

Claims (19)

  1. Organic light-emitting compounds represented by any one selected from [Chemical Formula A-1] to [Chemical Formula A-6] below: [Chemical Formula A-1] [Chemical Formula A-2] [Chemical Formula A-3] [Chemical Formula A-4] [Chemical Formula A-5] [Chemical Formula A-6] In the above [Chemical Formula A-1] to [Chemical Formula A-6], The above A11 to A17 are each identical or different and are selected from among an aromatic hydrocarbon ring having 6 to 24 carbon atoms that is independently substituted or unsubstituted, a condensed ring formed by the condensation of an aromatic hydrocarbon ring having 8 to 24 carbon atoms and an aliphatic hydrocarbon ring having 8 to 24 carbon atoms that is substituted or unsubstituted, and an aromatic heterocyclic ring having 2 to 24 carbon atoms that is substituted or unsubstituted. The above X is B, and The above Y 11 and Y 15 are each the same or different, and independently of each other are C or Si, and The above Y 12 is NR 1, CR 2 R 3 , It is one selected from O and S, and The above Y 13 is CR 2 R 3 , It is one selected from O and S, and The above Y 14 and Y 16 are each identical or different and are independently selected from CR 2 R 3 , SiR 4 R 5 , O, and S, and The above m and n are identical or different, and are independently 0 or 1, and when n is 0, this means that A 14 and A 15 are connected to each other by a single bond, so that the ring formed by A 14 , Y 11 , A 15 and Y 14 represents a five-membered ring, and In addition, when the above m is 0, this means that A 16 and A 17 are connected to each other by a single bond, so the ring formed by Y 15 , A 16 , Y 16 and A 17 represents a five-membered ring, and In the case where the above m or n is 1, this means that the ring formed by A 14 , Y 11 , A 15 and Y 14 is a six-membered ring, or the ring formed by Y 15 , A 16 , Y 16 and A 17 is a six-membered ring, and The above R1 to R5 are each the same or different and are independently selected from hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C50 heteroaryl group, and a substituted or unsubstituted C3 to C20 aliphatic aromatic mixed ring group. The above R2 and R3 , and R4 and R5 can each be connected to each other to additionally form a ring, and The substituents R1 to R3 in the above Y12 can additionally form a ring by combining with the above A12 or A13 ring, and Here, the term 'substituted or unsubstituted' in [Chemical Formula A-1] to [Chemical Formula A-6] refers to deuterium, cyano group, halogen group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 2 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, alkylamino group having 1 to 24 carbon atoms, diarylamino group having 12 to 24 carbon atoms, diheterolamino group having 2 to 24 carbon atoms, and carbon atoms having 7 to 24 carbon atoms. It means being substituted with one or more substituents selected from the group consisting of an aryl (heteroaryl)amino group, an alkylsilyl group having 1 to 24 carbon atoms, and an arylsilyl group having 6 to 24 carbon atoms.
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  3. In paragraph 1, An organic light-emitting compound characterized in that the above A 11 to A 17 are each identical or different and are independently substituted or unsubstituted aromatic hydrocarbon rings having 6 to 18 carbon atoms.
  4. In paragraph 3, An organic light-emitting compound characterized in that the aromatic hydrocarbon rings of A11 , A12 , A14 to A17 are each identical or different and are independently selected from any one of the following [Structural Formula 10] to [Structural Formula 21]. [Structural Formula 10] [Structural Formula 11] [Structural Formula 12] [Structural Formula 13] [Structural Formula 14] [Structural Formula 15] [Structural Formula 16] [Structural Formula 17] [Structural Formula 18] [Structural Formula 19] [Structural Formula 20] [Structural Formula 21] In the above [Structural Formula 10] to [Structural Formula 21], "-*" represents a bonding site for bonding with any one of the carbon atoms within the double bond in X, linkers Y 11 to Y 16 , and [Chemical Formula A-1] to [Chemical Formula A-6], respectively, and In the above [Structural Formula 10] to [Structural Formula 21], R is each the same or different and independently hydrogen, deuterium, cyano group, halogen group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, alkenyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, alkylamino group having 1 to 24 carbon atoms, diarylamino group having 12 to 24 carbon atoms, diheterolamino group having 2 to 24 carbon atoms, aryl (heteroaryl)amino group having 7 to 24 carbon atoms, and carbon atoms It is any one selected from 1 to 24 alkylsilyl groups and 6 to 24 carbon atoms in an arylsilyl group, and The above m is an integer from 1 to 8, and if m is 2 or greater, or if R is 2 or greater, each R may be the same or different from each other.
  5. In paragraph 3, An organic light-emitting compound characterized in that the aromatic hydrocarbon ring of A 13 above is a ring represented by the following [Structural Formula B]. [Structural Formula B] In the above [Structural Formula B], "-*" represents a bonding site for a carbon within the aromatic ring of the A 13 ring to bond with any one selected from linkers Y 11 , Y 12 , X, and linker Y 15 , and In the above [Structural Formula B], R 55 to R 57 are each the same or different and independently hydrogen, deuterium, cyano group, halogen group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, alkylamino group having 1 to 24 carbon atoms, diarylamino group having 12 to 24 carbon atoms, diheterolamino group having 2 to 24 carbon atoms, aryl(heteroaryl)amino group having 7 to 24 carbon atoms, alkylsilyl group having 1 to 24 carbon atoms It is any one selected from 6 to 24 arylsilyl groups, and The above R 55 to R 57 can each be connected to adjacent substituents to additionally form a ring.
  6. In paragraph 1, In the above [Chemical Formula A-1] and [Chemical Formula A-2], An organic light-emitting compound characterized in that at least one of the above A 11 to A 15 is a substituted or unsubstituted aromatic hydrocarbon ring having 7 to 18 carbon atoms.
  7. In paragraph 1, In the above [Chemical Formula A-1] and [Chemical Formula A-2], An organic light-emitting compound characterized in that the above A 12 is an aromatic heterocycle having 6 to 18 carbon atoms, comprising one or two aromatic ring heteroatoms selected from N, O, S, and Si.
  8. In paragraph 1, An organic light-emitting compound characterized in that the above Y 11 and Y 15 are each carbon atoms (C).
  9. In paragraph 1, In the above [Chemical Formula A-1] to [Chemical Formula A-4], An organic light-emitting compound characterized in that the above Y 12 is an oxygen (O) atom or NR 1 .
  10. In Paragraph 9, An organic light-emitting compound characterized in that the above R1 is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms.
  11. In Paragraph 10, An organic light-emitting compound characterized in that the above R1 is connected to an A12 or A13 ring to additionally form a ring.
  12. In paragraph 1, An organic light-emitting compound characterized in that the above Y 13 is an oxygen (O) or sulfur (S) atom.
  13. In paragraph 1, The compound represented by any one selected from [Chemical Formula A-1] to [Chemical Formula A-6] above is [Chemical Formula 1], [Chemical Formula 2], [Chemical Formula 4], [Chemical Formula 5], [Chemical Formula 7], [Chemical Formula 9] to [Chemical Formula 14], [Chemical Formula 16] to [Chemical Formula 18], [Chemical Formula 20] to [Chemical Formula 28], [Chemical Formula 34], [Chemical Formula 35], [Chemical Formula 39] to [Chemical Formula 46], [Chemical Formula 48] to [Chemical Formula 50], [Chemical Formula 53] to [Chemical Formula 56], [Chemical Formula 58], [Chemical Formula 60] to [Chemical Formula 62], [Chemical Formula 64] to [Chemical Formula 71], [Chemical Formula 76] to [Chemical Formula 78], [Chemical Formula 80], [Chemical Formula 82] to [Chemical Formula An organic light-emitting compound characterized by being one selected from [84]: [Chemical Formula 1] [Chemical Formula 2] [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 7] [Chemical Formula 9] [Chemical Formula 10] [Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14] [Chemical Formula 16] [Chemical Formula 17] [Chemical Formula 18] [Chemical Formula 20] [Chemical Formula 21] [Chemical Formula 22] [Chemical Formula 23] [Chemical Formula 24] [Chemical Formula 25] [Chemical Formula 26] [Chemical Formula 27] [Chemical Formula 28] [Chemical Formula 34] [Chemical Formula 35] [Chemical Formula 39] [Chemical Formula 40] [Chemical Formula 41] [Chemical Formula 42] [Chemical Formula 43] [Chemical Formula 44] [Chemical Formula 45] [Chemical Formula 46] [Chemical Formula 48] [Chemical Formula 49] [Chemical Formula 50] [Chemical Formula 53] [Chemical Formula 54] [Chemical Formula 55] [Chemical Formula 56] [Chemical Formula 58] [Chemical Formula 60] [Chemical Formula 61] [Chemical Formula 62] [Chemical Formula 64] [Chemical Formula 65] [Chemical Formula 66] [Chemical Formula 67] [Chemical Formula 68] [Chemical Formula 69] [Chemical Formula 70] [Chemical Formula 71] [Chemical Formula 76] [Chemical Formula 77] [Chemical Formula 78] [Chemical Formula 80] [Chemical Formula 82] [Chemical Formula 83] [Chemical Formula 84]
  14. First electrode; A second electrode facing the first electrode; and An organic light-emitting device comprising: an organic layer interposed between the first electrode and the second electrode; wherein the organic layer comprises one or more compounds represented by any one of [Chemical Formula A-1] to [Chemical Formula A-6] of any one of claims 1, 3 to 13.
  15. In Paragraph 14, An organic light-emitting device characterized in that the organic layer interposed between the first electrode and the second electrode comprises a light-emitting layer, the light-emitting layer is composed of a host and a dopant, and the compound is used as a dopant.
  16. In paragraph 15, The above organic light-emitting device is characterized by comprising, in addition to the light-emitting layer, at least one of a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function simultaneously, an electron transport layer, an electron injection layer, and a functional layer having an electron injection and electron transport function simultaneously.
  17. In paragraph 15, An organic light-emitting device characterized in that the host in the light-emitting layer is used by mixing or stacking two or more different compounds.
  18. In Paragraph 16, An organic light-emitting device characterized in that one or more layers selected from each of the above layers are formed by a deposition process or a solution process.
  19. In Paragraph 14, The above organic light-emitting element is characterized by being used in any one of the following devices: a flat panel display device; a flexible display device; a monochromatic or white flat panel lighting device; a monochromatic or white flexible lighting device; a vehicle display device; and a virtual or augmented reality display device.

Description

Novel boron compounds and organic light-emitting diode including the same The present invention relates to a novel boron compound and an organic light-emitting device containing the same, and more specifically, to a boron compound capable of realizing device characteristics such as high luminous efficiency and long lifespan when used as a dopant material in the light-emitting layer of an organic light-emitting device, and an organic light-emitting device containing the same. Organic light-emitting diodes (OLEDs) are displays that utilize the self-luminous phenomenon and have advantages such as a large viewing angle, thinness and compactness compared to liquid crystal displays, and fast response speed, so applications as full-color displays or lighting are expected. Generally, organic light emission refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting diodes (OLEDs) that utilize this phenomenon typically have a structure comprising 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 enhance the efficiency and stability of the OLED; for example, it may consist of a hole injection layer, a hole transport layer, an emissive layer, an electron transport layer, and an electron injection layer. In the structure of such an OLED, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and light is emitted when these excitons fall back to the ground state. Such OLEDs are known to possess characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, a wide viewing angle, high contrast, and high-speed response. Materials used as organic layers in organic light-emitting devices can be classified according to their function into light-emitting materials and charge-transporting materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials. The light-emitting materials can be classified into high-molecular-weight and low-molecular-weight types according to their molecular weight, and can be classified according to their light emission mechanism into fluorescent materials derived from the singlet excited state of electrons and phosphorescent materials derived from the triplet excited state of electrons. Meanwhile, when only one material is used as the light-emitting material, problems arise such as the maximum emission wavelength shifting to a longer wavelength due to intermolecular interactions, resulting in reduced color purity or decreased device efficiency due to light attenuation effects; therefore, a host-dopant system can be used as the light-emitting material to increase color purity and luminescence efficiency through energy transfer. The principle is that when a small amount of a dopant with 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, producing high-efficiency light. At this time, since the wavelength of the host shifts to the wavelength range of the dopant, light of a desired wavelength can be obtained depending on the type of dopant used. Recently, boron compounds have been studied as dopant compounds among these light-emitting layers. As prior art related to this, Korean Patent Publication No. 10-2016-0119683 (October 14, 2016) discloses a polycyclic aromatic compound in which a plurality of aromatic rings are connected by boron atoms and oxygen atoms, and an organic light-emitting device containing the same. In International Patent Publication No. 2017-188111 (November 02, 2017), an organic light-emitting device is described in which a compound having a structure in which a plurality of condensed aromatic rings are connected by boron atoms and nitrogen is used as a dopant in the light-emitting layer, and an anthracene derivative is used as a host. However, despite the fact that various types of compounds for use in the light-emitting layer of organic light-emitting diodes, including the aforementioned prior art, have been manufactured and applied to organic light-emitting diodes, there is still a continuous demand for the development of organic light-emitting diodes with high-efficiency characteristics such as high luminous efficiency and long lifespan. FIG. 1 is a schematic diagram of an organic light-emitting element according to one embodiment of the present invention. The present invention will be described in more detail below. In each drawing of the present invention, the sizes or dimensions of the structures are depicted enlarged or reduced compared to the actual size for the sake of clarity of the invention, and known components are