WO2024144206A1 - Compound and organic electroluminescent device comprising same - Google Patents

Compound and organic electroluminescent device comprising same Download PDF

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WO2024144206A1
WO2024144206A1 PCT/KR2023/021584 KR2023021584W WO2024144206A1 WO 2024144206 A1 WO2024144206 A1 WO 2024144206A1 KR 2023021584 W KR2023021584 W KR 2023021584W WO 2024144206 A1 WO2024144206 A1 WO 2024144206A1
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aryl
nuclear atoms
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alkyl
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이용환
심재의
배형찬
박우재
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솔루스첨단소재 주식회사
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Definitions

  • the present invention relates to a novel compound and an organic electroluminescent device containing the same. More specifically, it relates to a compound with excellent electron injection and transport ability and thermal stability, and its inclusion in one or more organic layers to improve luminous efficiency, driving voltage, lifespan, etc. It relates to an organic electroluminescent device with improved characteristics.
  • Materials for forming the light-emitting layer of an organic EL device can be classified into blue, green, and red light-emitting materials depending on the color of the light.
  • yellow and orange luminescent materials are also used as luminescent materials to realize better natural colors.
  • a host/dopant system can be used as a luminescent material.
  • Dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. The development of these phosphorescent materials can theoretically improve luminous efficiency by up to 4 times compared to fluorescence, so interest is focused on not only phosphorescent dopants but also phosphorescent host materials.
  • the purpose of the present invention is to provide a new compound with improved electron injection and transport capabilities and excellent thermal stability that can be used as an organic layer material of an organic electroluminescent device, specifically an electron transport layer material or an electron transport auxiliary layer material.
  • Another object of the present invention is to provide an organic electroluminescent device with low driving voltage, high luminous efficiency, and improved lifespan characteristics, including the novel compound described above.
  • the present invention provides a compound represented by the following formula (1):
  • X 1 is C, Si, Ge or Sn
  • a 1 to A 5 are each N or CR
  • At least one of A 1 to A 5 is CR, and in this case, one of the CRs other than N is connected to L 4 ,
  • a plurality of R is the same or different from each other,
  • g is an integer from 0 to 4,
  • R and R 1 to R 5 are the same or different from each other, and are each independently hydrogen, deuterium (D), halogen group, cyano group, nitro group, amino group, C 1 to C 40 alkyl group, C 2 to C 40 alkene. Nyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms.
  • Ar 1 and Ar 2 are the same as or different from each other, and are each independently hydrogen, deuterium (D), halogen group, cyano group, nitro group, amino group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 arylphosphine group, C 6 ⁇ C 60 arylphosphine oxide group, C 6 ⁇ C 60 arylger
  • the organic material layer containing the above compound may be an electron transport layer or an electron transport auxiliary layer.
  • the compound according to the present invention has excellent electron transport and injection capabilities, heat resistance, electrochemical stability, etc., so it can be used as an organic material layer material for organic electroluminescent devices.
  • an organic electroluminescent device with excellent light emission performance, low driving voltage, high efficiency, fast mobility, and long lifespan characteristics compared to conventional materials can be produced. It is possible to manufacture full-color display panels with improved performance and lifespan.
  • FIG. 1 is a cross-sectional view schematically showing an organic electroluminescent device according to a first embodiment of the present invention.
  • 300 organic material layer
  • 310 hole injection layer
  • the first ring moiety is a benzene ring moiety or a 6-membered heterocyclic moiety, and the first ring moiety has a functional group containing a group 14 element of the periodic table (hereinafter referred to as 'group 14 element -containing functional group') is combined.
  • the Group 14 elements may include carbon (C), silicon (Si), germanium (Ge), and tin (Sn), but are not limited thereto. Because the compound of the present invention contains a Group 14 element-containing functional group, conjugation is broken and it can have a bulky shape.
  • the triazine moiety is an electron withdrawing group (EWG) with high electron absorption, and is connected to the second ring moiety (specifically, benzene) directly or through a linker group (L 5 ). ring moiety).
  • EWG electron withdrawing group
  • L 5 linker group
  • the first moiety ( ), second moiety ( ) and the third moiety ( ) can be bonded to various positions of the phenyl ring.
  • the first to third moieties are bonded to positions 1, 2, and 3 of the phenyl ring, it is difficult to synthesize the compound, and each moiety has a structure that is excessively bent around the phenyl ring. , performance may not improve.
  • the first to third moieties are centered around the phenyl ring at positions 1, 2, and 4 of the phenyl ring, positions 1, 3, and 5 of the phenyl ring, or positions 1 of the phenyl ring. , may be bonded to positions 3 or 6, or to positions 1, 4, or 5 of the phenyl ring.
  • X 1 , A 1 to A 5 , A, B, C, D, E, F, G, L 1 to L 6 , AR 1 , AR 2 , and R 1 to R 5 are as defined in Formula 1, respectively. .
  • a 1 to A 5 are each N or CR. However, at least one of A 1 to A 5 is CR, and in this case, one of the CRs other than N is connected to L 4 , and the plurality of R's are the same or different from each other.
  • the phosphine group, arylphosphine oxide group, arylgermyl group, arylamine group, heteroarylamine group, and (aryl)(heteroaryl)amine group each independently contain deuterium (D), halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 ⁇ C 60 Aryl group, heteroaryl group with 5 to 60 nuclear
  • L 1 to L 6 are each divalent linker groups, C 6 to C 30 arylene groups, and the number of nuclear atoms. It is selected from the group consisting of a heteroarylene group having 5 to 30 atoms and an ether group (-O-), and specifically, an arylene group having C 6 to C 18 , a heteroarylene group having 5 to 18 nuclear atoms, and an ether group (-O- ) can be selected from the group consisting of
  • a plurality of L 1 to a plurality of L 6 may be the same or different from each other.
  • the arylene group and heteroarylene group of L 1 to L 6 are each independently selected from deuterium (D), halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C Substituted or unsubstituted with one or more substituents selected from the group consisting of 60 aryl boron group, C 6 ⁇ C 60 arylphosphine group, C 6 ⁇ C 60 ary
  • o and p are each integers from 0 to 4,
  • the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, and alkylboron group of Ar 1 and Ar 2 , aryl boron group, aryl phosphine group, aryl phosphine oxide group, aryl germyl group, aryl amine group, heteroaryl amine group, and (aryl) (heteroaryl) amine group are each independently deuterium (D), halogen, and cyano group.
  • nitro group C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, Aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C 1 to C 40 , aryloxy group of C 6 to C 60 , alkylsilyl group of C 1 to C 40 , C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 arylphosphine group, C 6 ⁇ C 60 arylphosphine oxide It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups and C 6 to C 60 arylamine groups. At this time,
  • g is an integer from 0 to 4.
  • R 4 are the same or different from each other, and are each independently hydrogen, deuterium (D), halogen group, cyano group, nitro group, amino group, C 1 to C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 ⁇ C 60 aryl group , heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C 40 alkyl boron group, C 6
  • the heterocycloalkyl group and heteroaryl group may each include one or more heteroatoms selected from the group consisting of N, S, O, Ge, P, Sn, and Se, while the condensed ring has C 3 ⁇ C 60
  • a condensed aliphatic ring specifically, a condensed aliphatic ring of C 3 to C 30
  • a fused aromatic ring of C 6 to C 60 specifically, a fused aromatic ring of C 6 to C 30
  • a 5- to 60-membered condensed ring It may be one or more types selected from the group consisting of heteroaromatic rings (specifically, 5- to 30-membered condensed heteroaromatic rings).
  • one or more R 4 are the same or different from each other, and each independently represents deuterium (D), an alkyl group of C 1 to C 20 , an aryl group of C 6 to C 30 and a hetero group of 5 to 30 nuclear atoms. selected from the group consisting of aryl groups, or adjacent groups (e.g. R 4 -R 3 , R 4 -L 3 , R 4 -L 1 , R 4 -L 4 , R 4 -R 1 ) can be combined to form a condensed aromatic ring of C 3 to C 30 , and more specifically, each independently an aryl group of C 6 to C 30 , and a heteroaryl group of 5 to 30 nuclear atoms.
  • D deuterium
  • an alkyl group of C 1 to C 20 an aryl group of C 6 to C 30 and a hetero group of 5 to 30 nuclear atoms.
  • R 4 -R 1 selected from the group consisting of aryl groups, or adjacent groups (e.g. R 4 -
  • a6 is an integer from 0 to 2
  • Ring Cy1 is a fused aromatic ring of C 6 to C 18 or a fused heteroaromatic ring of 5 to 21 nuclear atoms,
  • alkyl boron group refers to a boron group substituted with alkyl having 1 to 40 carbon atoms
  • aryl boron group refers to a boron group substituted with aryl having 6 to 60 carbon atoms.
  • the compound of Formula 1 may be used alone or mixed with materials for the electron transport layer auxiliary layer known in the art.
  • triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol)
  • 2-(4-bromo-3-chlorophenyl)- 4,6-diphenyl-1,3,5-triazine (4.22 g, 10 mmol)
  • Pd(PPh 3 ) 4 (0.34 g, 0.3 mmol)
  • K 2 CO 3 (2.76 g, 20 mmol) in 1, 100 ml of 4-Dioxane/25 ml of H 2 O was added and stirred at 100°C for 8 hours.
  • triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol)
  • 2-(2-bromo-5-chlorophenyl)- 4,6-diphenyl-1,3,5-triazine (4.22 g, 10 mmol)
  • Pd(PPh 3 ) 4 (0.34 g, 0.3 mmol)
  • K 2 CO 3 (2.76 g, 20 mmol) in 1, 100 ml of 4-Dioxane/25 ml of H 2 O was added and stirred at 100°C for 8 hours.
  • triphenyl(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-(3-bromo-5-chlorophenyl)- 4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (5.12 g, 10 mmol), Pd(PPh 3 ) 4 (0.34 g, 0.3 mmol), and K 2 CO 3 (2.76 g, 20 mmol) was added to 100 ml of 1,4-Dioxane/25 ml of H 2 O and stirred at 100°C for 8 hours.
  • triphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol)
  • 2-([1,1'-biphenyl]- 4-yl)-4-(3-bromo-5-chlorophenyl)-6-phenyl-1,3,5-triazine (4.98 g, 10 mmol)
  • Pd(PPh 3 ) 4 (0.34 g, 0.3 mmol)
  • K 2 CO 3 (2.76 g, 20 mmol) were added to 100 ml of 1,4-Dioxane/25 ml of H 2 O and stirred at 100°C for 8 hours.
  • triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)germane (5.07 g, 10 mmol), 2-(3-bromo-5-chlorophenyl)- 4,6-diphenyl-1,3,5-triazine (4.22 g, 10 mmol), Pd(PPh 3 ) 4 (0.34 g, 0.3 mmol), and K 2 CO 3 (2.76 g, 20 mmol) in 1, 100 ml of 4-Dioxane/25 ml of H 2 O was added and stirred at 100°C for 8 hours.
  • Example 1 One 4.0 454 7.9
  • Example 2 2 4.9 455 6.1
  • Example 3 3 4.5 456 6.0
  • Example 4 4 4.9 459 6.9
  • Example 5 5 4.1 452 6.1
  • Example 6 4.2 454 6.3
  • Example 7 7 5.0 455 7.5
  • Example 8 8 5.1 458 7.2
  • Example 9 9 4.9 452 6.1
  • Example 10 10 4.9 459 7.0
  • Example 11 121 4.0 455 6.9
  • Example 12 122 4.1 456 6.8
  • Example 13 123 4.2 457 6.6 Comparative Example 1 HB1 5.1 458 5.9

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Abstract

The present invention relates to a novel compound and an organic electroluminescent device using same and, more specifically, to a compound having excellent electron injection and transport ability and excellent thermal stability, and an organic electroluminescent device including the compound in one or more organic material layers thereof, thus having improved characteristics in terms of luminescence efficiency, driving voltage, lifespan, and the like.

Description

화합물 및 이를 포함하는 유기 전계 발광 소자Compounds and organic electroluminescent devices containing them
본 발명은 신규한 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것으로, 보다 상세하게는 전자 주입 및 수송능 및 열적 안정성이 우수한 화합물 및 이를 하나 이상의 유기물층에 포함함으로써 발광효율, 구동 전압, 수명 등의 특성이 향상된 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel compound and an organic electroluminescent device containing the same. More specifically, it relates to a compound with excellent electron injection and transport ability and thermal stability, and its inclusion in one or more organic layers to improve luminous efficiency, driving voltage, lifespan, etc. It relates to an organic electroluminescent device with improved characteristics.
유기 전계 발광 소자(이하, '유기 EL 소자')는 두 전극 사이에 전압을 걸어 주면 양극에서는 정공이 주입되고, 음극에서는 전자가 유기물층으로 주입된다. 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥상태로 떨어질 때 빛이 나게 된다. 이때 유기물층으로 사용되는 물질은 그 기능에 따라, 발광 물질, 정공 주입 물질, 정공 수송 물질, 전자 수송 물질, 전자 주입 물질 등으로 분류될 수 있다. When a voltage is applied between two electrodes in an organic electroluminescent device (hereinafter referred to as 'organic EL device'), holes are injected from the anode and electrons are injected from the cathode into the organic material layer. When the injected hole and electron meet, an exciton is formed, and when this exciton falls to the ground state, light is emitted. At this time, the material used as the organic material layer can be classified into light-emitting material, hole injection material, hole transport material, electron transport material, electron injection material, etc., depending on its function.
유기 EL 소자의 발광층 형성재료는 발광색에 따라 청색, 녹색, 적색 발광 재료로 구분될 수 있다. 그 밖에, 보다 나은 천연색을 구현하기 위한 발광재료로 노란색 및 주황색 발광재료도 사용된다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 재료로서 호스트/도펀트 계를 사용할 수 있다. 도판트 물질은 유기 물질을 사용하는 형광 도판트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도판트로 나눌 수 있다. 이러한 인광 재료의 개발은 이론적으로 형광에 비해 4배까지의 발광 효율을 향상시킬 수 있어 인광 도판트 뿐만 아니라 인광 호스트 재료들에 대해 관심이 집중되고 있다. Materials for forming the light-emitting layer of an organic EL device can be classified into blue, green, and red light-emitting materials depending on the color of the light. In addition, yellow and orange luminescent materials are also used as luminescent materials to realize better natural colors. Additionally, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system can be used as a luminescent material. Dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. The development of these phosphorescent materials can theoretically improve luminous efficiency by up to 4 times compared to fluorescence, so interest is focused on not only phosphorescent dopants but also phosphorescent host materials.
현재까지 정공 주입층, 정공 수송층. 정공 차단층, 전자 수송층으로는, 하기 화학식으로 표현된 NPB, BCP, Alq3 등이 널리 알려져 있고, 발광 재료는 안트라센 유도체들이 형광 도판트/호스트 재료로서 보고되고 있다. 특히 발광재료 중 효율 향상 측면에서 큰 장점을 가지고 있는 인광 재료로서는 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물이 청색, 녹색, 적색 도판트 재료로 사용되고 있다. 현재까지는 CBP가 인광 호스트 재료로 우수한 특성을 나타내고 있다. So far, hole injection layer and hole transport layer. As hole blocking layers and electron transport layers, NPB, BCP, and Alq 3 expressed by the following chemical formulas are widely known, and as light emitting materials, anthracene derivatives have been reported as fluorescent dopant/host materials. In particular, among light emitting materials, phosphorescent materials that have great advantages in terms of efficiency improvement include metal complex compounds containing Ir such as Firpic, Ir(ppy) 3 , (acac)Ir(btp) 2 , etc., which are used as blue, green, and red dopant materials. It is being used as. To date, CBP has shown excellent properties as a phosphorescent host material.
그러나 종래의 유기물층 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮고 열적 안정성이 매우 좋지 않아 유기 EL 소자에서의 수명 측면에서 만족할 만한 수준이 되지 못하고 있다. 따라서, 성능이 뛰어난 유기물층 재료의 개발이 요구되고 있다.However, although conventional organic layer materials have advantages in terms of luminescence characteristics, they have low glass transition temperatures and very poor thermal stability, so they are not satisfactory in terms of lifespan in organic EL devices. Therefore, the development of organic layer materials with excellent performance is required.
본 발명은 전자 주입 및 수송능이 개선되고, 열안정성이 우수하여 유기 전계 발광 소자의 유기물층 재료, 구체적으로 전자수송층 재료나 전자수송 보조층 재료 등으로 사용될 수 있는 신규 화합물을 제공하는 것을 목적으로 한다.The purpose of the present invention is to provide a new compound with improved electron injection and transport capabilities and excellent thermal stability that can be used as an organic layer material of an organic electroluminescent device, specifically an electron transport layer material or an electron transport auxiliary layer material.
또한, 본 발명은 전술한 신규 화합물을 포함하여 구동전압이 낮고, 발광 효율이 높으며, 수명 특성이 향상된 유기 전계 발광 소자를 제공하는 것을 또 다른 목적으로 한다.Another object of the present invention is to provide an organic electroluminescent device with low driving voltage, high luminous efficiency, and improved lifespan characteristics, including the novel compound described above.
상기한 목적을 달성하기 위해, 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다:In order to achieve the above object, the present invention provides a compound represented by the following formula (1):
Figure PCTKR2023021584-appb-img-000001
Figure PCTKR2023021584-appb-img-000001
(상기 화학식 1에서,(In Formula 1 above,
X1은 C, Si, Ge 또는 Sn이고,X 1 is C, Si, Ge or Sn,
A1 내지 A5는 각각 N 또는 CR이고, A 1 to A 5 are each N or CR,
다만 A1 내지 A5 중 적어도 하나는 CR이고, 이때 N이 아닌 CR 중 하나는 L4와 연결되고, However, at least one of A 1 to A 5 is CR, and in this case, one of the CRs other than N is connected to L 4 ,
복수의 R은 서로 동일하거나 상이하며,A plurality of R is the same or different from each other,
a, b, c, d, e 및 f는 각각 0 내지 3의 정수이고,a, b, c, d, e and f are each integers from 0 to 3,
g는 0 내지 4의 정수이며,g is an integer from 0 to 4,
L1 내지 L6는 서로 동일하거나 상이하고, 각각 독립적으로 직접 결합이거나, 또는 C6~C30의 아릴렌기, 핵원자수 5 내지 30개의 헤테로아릴렌기 및 에테르기(-O-)로 이루어진 군에서 선택되고,L 1 to L 6 are the same or different from each other, and are each independently a direct bond, or a group consisting of an arylene group of C 6 to C 30 , a heteroarylene group of 5 to 30 nuclear atoms, and an ether group (-O-) is selected from,
R 및 R1 내지 R5는 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소(D), 할로겐기, 시아노기, 니트로기, 아미노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, C6~C60의 아릴게르밀기, C6~C60의 아릴아민기, 핵원자수 5 내지 60의 헤테로아릴아민기, (C6~C60의 아릴)(핵원자수 5 내지 60의 헤테로아릴)아민기로 이루어진 군에서 선택되거나, 또는 인접하는 기와 축합하여 축합 고리를 형성하고,R and R 1 to R 5 are the same or different from each other, and are each independently hydrogen, deuterium (D), halogen group, cyano group, nitro group, amino group, C 1 to C 40 alkyl group, C 2 to C 40 alkene. Nyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms. , C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group , C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 arylphosphine oxide group, C 6 ~ C 60 arylgermyl group, C 6 ~ C 60 aryl Selected from the group consisting of an amine group, a heteroarylamine group having 5 to 60 nuclear atoms, (aryl of C 6 to C 60 ) (heteroaryl of 5 to 60 nuclear atoms) amine group, or condensed by condensation with an adjacent group. forming a ring,
Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소(D), 할로겐기, 시아노기, 니트로기, 아미노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, C6~C60의 아릴게르밀기, C6~C60의 아릴아민기, 핵원자수 5 내지 60의 헤테로아릴아민기, (C6~C60의 아릴)(핵원자수 5 내지 60의 헤테로아릴)아민기로 이루어진 군에서 선택되거나, 또는 인접한 기와 서로 결합하여 축합 고리를 형성할 수 있고;Ar 1 and Ar 2 are the same as or different from each other, and are each independently hydrogen, deuterium (D), halogen group, cyano group, nitro group, amino group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 arylphosphine oxide group, C 6 ~ C 60 arylgermyl group, C 6 ~ C 60 arylamine group , heteroarylamine group having 5 to 60 nuclear atoms, (aryl of C 6 to C 60 ) (heteroaryl of 5 to 60 nuclear atoms) amine group, or bonded with adjacent groups to form a condensed ring. can be formed;
상기 L1 내지 L6의 아릴렌기 및 헤테로아릴렌기와, 상기 R, R1 내지 R5와 Ar1 및 Ar2의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기, 아릴게르밀기, 아릴아민기, 헤테로아릴아민기 및 (아릴)(헤테로아릴)아민기는, 각각 독립적으로 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이함).The arylene group and heteroarylene group of L 1 to L 6 , the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl of R, R 1 to R 5 and Ar 1 and Ar 2 group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylgermyl group, arylamine group, heteroarylamine group and ( Aryl) (heteroaryl) amine group each independently represents deuterium (D), halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, and C 2 to C 40 alkynyl group. , C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group. , C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group , C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 arylphosphine oxide group, and C 6 ~ C 60 arylamine group. In this case, the substituent is substituted or unsubstituted with one or more types of substituents selected from the group consisting of If is plural, they are the same or different from each other).
또, 본 발명은 애노드; 캐소드; 상기 애노드와 캐소드 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중 적어도 하나는 전술한 화합물을 포함하는 유기 전계 발광 소자를 제공한다.In addition, the present invention is an anode; cathode; Provided is an organic electroluminescent device comprising one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers containing the above-described compound.
상기 화합물을 포함하는 유기물층은 전자수송층 또는 전자수송 보조층일 수 있다.The organic material layer containing the above compound may be an electron transport layer or an electron transport auxiliary layer.
본 발명에 따른 화합물은 전자 수송 및 주입능, 내열성, 전기화학적 안정성 등이 우수하기 때문에 유기 전계 발광 소자의 유기물층 재료로 사용될 수 있다. 특히, 본 발명의 화합물을 전자수송층 재료 또는 전자수송 보조층 재료로 사용할 경우, 종래 재료에 비해 우수한 발광 성능, 낮은 구동전압, 높은 효율, 빠른 모빌리티(mobility) 및 장수명 특성을 갖는 유기 전계 발광 소자를 제조할 수 있고, 나아가 성능 및 수명이 향상된 풀 칼라 디스플레이 패널도 제조할 수 있다.The compound according to the present invention has excellent electron transport and injection capabilities, heat resistance, electrochemical stability, etc., so it can be used as an organic material layer material for organic electroluminescent devices. In particular, when the compound of the present invention is used as an electron transport layer material or an electron transport auxiliary layer material, an organic electroluminescent device with excellent light emission performance, low driving voltage, high efficiency, fast mobility, and long lifespan characteristics compared to conventional materials can be produced. It is possible to manufacture full-color display panels with improved performance and lifespan.
도 1은 본 발명의 제1 실시 형태에 따른 유기 전계 발광 소자를 개략적으로 나타낸 단면도이다.1 is a cross-sectional view schematically showing an organic electroluminescent device according to a first embodiment of the present invention.
도 2는 본 발명의 제2 실시 형태에 따른 유기 전계 발광 소자를 개략적으로 나타낸 단면도이다. Figure 2 is a cross-sectional view schematically showing an organic electroluminescent device according to a second embodiment of the present invention.
도 3은 본 발명의 제3 실시 형태에 따른 유기 전계 발광 소자를 개략적으로 나타낸 단면도이다. Figure 3 is a cross-sectional view schematically showing an organic electroluminescent device according to a third embodiment of the present invention.
<부호의 설명><Explanation of symbols>
100: 애노드, 200: 캐소드,100: anode, 200: cathode,
300: 유기물층, 310: 정공주입층,300: organic material layer, 310: hole injection layer,
320: 정공수송층, 330: 발광층,320: hole transport layer, 330: light emitting layer,
340: 전자수송층, 350: 전자주입층,340: electron transport layer, 350: electron injection layer,
360: 전자수송 보조층360: Electron transport auxiliary layer
이하, 본 발명에 대해 설명한다.Hereinafter, the present invention will be described.
<신규 화합물><New compound>
본 발명에 따른 화합물은 주기율표상의 14족 원소를 함유하는 작용기가 결합된 제1 환 모이어티; 상기 제1 환 모이어티에 직접 또는 링커기(L4)를 통해 결합된 제2 환 모이어티; 및 상기 제2 환 모이어티에 직접 또는 링커기(L5)를 통해 결합된 트리아진 모이어티(triazine moiety)를 포함하는 구조로, 상기 화학식 1로 표시된다. 이러한 화학식 1로 표시되는 본원발명의 화합물은 전자 주입 및 수송능, 전기화학적 안정성, 내열성 등이 우수하여 유기 전계 발광 소자의 고효율, 장수명, 구동전압 특성을 향상시킬 수 있는 전자수송층 재료 또는 전자수송 보조층 재료로 사용될 수 있다.The compound according to the present invention includes a first ring moiety to which a functional group containing an element of group 14 of the periodic table is bonded; a second ring moiety bonded to the first ring moiety directly or through a linker group (L 4 ); and a triazine moiety bonded to the second ring moiety directly or through a linker group (L 5 ), and is represented by Formula 1. The compound of the present invention represented by Formula 1 has excellent electron injection and transport ability, electrochemical stability, and heat resistance, and can be used as an electron transport layer material or electron transport auxiliary to improve the high efficiency, long life, and driving voltage characteristics of organic electroluminescent devices. Can be used as a layer material.
본 발명에 따른 화합물에서, 제1 환 모이어티는 벤젠환 모이어티 또는 6원-헤테로환 모이어티로, 상기 제1 환 모이어티에는 주기율표상의 14족 원소를 함유하는 작용기(이하, '14족 원소-함유 작용기')가 결합되어 있다. 상기 14족 원소의 예로는 탄소(C), 규소(Si), 게르마늄(Ge), 주석(Sn) 등일 수 있는데, 이에 한정되지 않는다. 본 발명의 화합물이 14족 원소-함유 작용기를 함유함으로써, 컨쥬게이션(conjugation)이 끊어지고, 벌키(bulky)한 형상을 가질 수 있다. 이로 인해, 본 발명의 화합물은 높은 삼중항 에너지(triplet energy)와 높은 밴드 갭(band gap)을 갖게 되어 정공 및 전자의 밸런스(balance)를 조절할 수 있고, 높은 T1 에너지로 인해 엑시톤(exciton)을 호스트 측으로 모이게 하면서, 엑시톤이 역으로 넘어오는 것을 방지할 수 있어 소자 효율 및 수명을 증가시킬 수 있다.In the compound according to the present invention, the first ring moiety is a benzene ring moiety or a 6-membered heterocyclic moiety, and the first ring moiety has a functional group containing a group 14 element of the periodic table (hereinafter referred to as 'group 14 element -containing functional group') is combined. Examples of the Group 14 elements may include carbon (C), silicon (Si), germanium (Ge), and tin (Sn), but are not limited thereto. Because the compound of the present invention contains a Group 14 element-containing functional group, conjugation is broken and it can have a bulky shape. Due to this, the compound of the present invention has high triplet energy and high band gap, so it can control the balance of holes and electrons, and generates exciton due to high T1 energy. By converging on the host side, excitons can be prevented from crossing over, thereby increasing device efficiency and lifespan.
또한, 본 발명에 따른 화합물에서, 트리아진 모이어티는 전자흡수성이 큰 전자끌게기(electron withdrawing group, EWG)로, 직접 또는 링커기(L5)를 통해 제2 환 모이어티(구체적으로, 벤젠환 모이어티)에 결합된다. 이러한 트리아진 모이어티는 전자 이동도를 향상시켜 화합물의 전자 수송 및 주입성을 향상시킬 수 있다. 따라서, 본 발명에 따른 화합물이 유기 전계 발광 소자의 전자 수송층 또는 전자수송 보조층의 재료로 적용될 경우, 전자는 음극(또는 전자 주입층)에서 발광층으로 원활히 전달될 수 있고, 그 결과 소자의 구동전압이 낮아지고, 고효율 및 장수명 특성이 구현될 수 있다. In addition, in the compound according to the present invention, the triazine moiety is an electron withdrawing group (EWG) with high electron absorption, and is connected to the second ring moiety (specifically, benzene) directly or through a linker group (L 5 ). ring moiety). These triazine moieties can improve electron mobility and improve the electron transport and injection properties of the compound. Therefore, when the compound according to the present invention is applied as a material for the electron transport layer or electron transport auxiliary layer of an organic electroluminescent device, electrons can be smoothly transferred from the cathode (or electron injection layer) to the light emitting layer, and as a result, the driving voltage of the device can be increased. is lowered, and high efficiency and long life characteristics can be realized.
전술한 바와 같이, 본 발명에 따른 화학식 1로 표시되는 화합물은 전자 주입 및 수송능, 열적 안정성, 전기화학적 안정성 등이 우수하다. 따라서, 본 발명의 화합물은 유기 전계 발광 소자의 유기물층, 바람직하게 전자수송 보조층 재료로 사용될 수 있다. 이러한 본 발명의 화합물을 포함하는 유기 전계 발광소자는 성능 및 수명 특성이 크게 향상될 수 있고, 이러한 유기 전계 발광 소자가 적용된 풀 칼라 유기 발광 패널도 성능이 극대화될 수 있다.As described above, the compound represented by Formula 1 according to the present invention is excellent in electron injection and transport ability, thermal stability, electrochemical stability, etc. Therefore, the compound of the present invention can be used as a material for the organic material layer of an organic electroluminescent device, preferably as an electron transport auxiliary layer material. The performance and lifespan characteristics of an organic electroluminescent device containing the compound of the present invention can be greatly improved, and a full-color organic light emitting panel to which such an organic electroluminescent device is applied can also maximize performance.
본 발명에 따른 화학식 1로 표시되는 화합물에서, 제1 모이어티(
Figure PCTKR2023021584-appb-img-000002
), 제2 모이어티(
Figure PCTKR2023021584-appb-img-000003
) 및 제3 모이어티 (
Figure PCTKR2023021584-appb-img-000004
)가 페닐 고리의 다양한 위치에 결합될 수 있다. 다만, 상기 제1 내지 제3 모이어티가 각각 페닐 고리의 1, 2, 3번 위치에 결합될 경우, 화합물을 합성하기 어렵고, 또 페닐 고리를 중심으로 각 모이어티가 과도하게 꺾이는 구조를 갖기 때문에, 성능이 개선되지 않을 수 있다. 이에, 본 발명의 화합물에서, 상기 제1 내지 제3 모이어티는 페닐 고리를 중심으로 페닐 고리의 1, 2, 4번 위치나, 페닐 고리의 1, 3, 5번 위치, 또는 페닐 고리의 1, 3, 6번 위치, 혹은 페닐 고리의 1, 4, 5번 위치 중 하나에 결합될 수 있다.In the compound represented by Formula 1 according to the present invention, the first moiety (
Figure PCTKR2023021584-appb-img-000002
), second moiety (
Figure PCTKR2023021584-appb-img-000003
) and the third moiety (
Figure PCTKR2023021584-appb-img-000004
) can be bonded to various positions of the phenyl ring. However, when the first to third moieties are bonded to positions 1, 2, and 3 of the phenyl ring, it is difficult to synthesize the compound, and each moiety has a structure that is excessively bent around the phenyl ring. , performance may not improve. Accordingly, in the compound of the present invention, the first to third moieties are centered around the phenyl ring at positions 1, 2, and 4 of the phenyl ring, positions 1, 3, and 5 of the phenyl ring, or positions 1 of the phenyl ring. , may be bonded to positions 3 or 6, or to positions 1, 4, or 5 of the phenyl ring.
이러한 제1 내지 제3 모이어티의 결합 위치에 따라, 상기 화학식 1로 표시되는 화합물은 하기 화학식 2 내지 8 중 어느 하나로 표시되는 화합물로 구체화될 수 있는데, 이에 한정되지 않는다.Depending on the binding positions of the first to third moieties, the compound represented by Formula 1 may be specified as a compound represented by any one of the following Formulas 2 to 8, but is not limited thereto.
Figure PCTKR2023021584-appb-img-000005
Figure PCTKR2023021584-appb-img-000005
Figure PCTKR2023021584-appb-img-000006
Figure PCTKR2023021584-appb-img-000006
Figure PCTKR2023021584-appb-img-000007
Figure PCTKR2023021584-appb-img-000007
Figure PCTKR2023021584-appb-img-000008
Figure PCTKR2023021584-appb-img-000008
Figure PCTKR2023021584-appb-img-000009
Figure PCTKR2023021584-appb-img-000009
Figure PCTKR2023021584-appb-img-000010
Figure PCTKR2023021584-appb-img-000010
Figure PCTKR2023021584-appb-img-000011
Figure PCTKR2023021584-appb-img-000011
상기 화학식 2 내지 8에서,In Formulas 2 to 8,
X1, A1 내지 A5, a, b, c, d, e, f, g, L1 내지 L6, Ar1, Ar2, 및 R1 내지 R5는 각각 상기 화학식 1에서 정의한 바와 같다.X 1 , A 1 to A 5 , A, B, C, D, E, F, G, L 1 to L 6 , AR 1 , AR 2 , and R 1 to R 5 are as defined in Formula 1, respectively. .
상기 화학식 1로 표시되는 화합물에서, X1은 C, Si, Ge 또는 Sn이고, 구체적으로 Si, Ge 또는 Sn일 수 있다. 일례로 X1은 Si일 수 있다.In the compound represented by Formula 1, X 1 may be C, Si, Ge, or Sn, and may specifically be Si, Ge, or Sn. For example, X 1 may be Si.
상기 화학식 1로 표시되는 화합물에서, A1 내지 A5는 각각 N 또는 CR이다. 다만, A1 내지 A5 중 적어도 하나는 CR이고, 이때 N이 아닌 CR 중 하나는 L4와 연결되고, 복수의 R은 서로 동일하거나 상이하다.In the compound represented by Formula 1, A 1 to A 5 are each N or CR. However, at least one of A 1 to A 5 is CR, and in this case, one of the CRs other than N is connected to L 4 , and the plurality of R's are the same or different from each other.
하나 이상의 R은 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소(D), 할로겐기, 시아노기, 니트로기, 아미노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, C6~C60의 아릴게르밀기, C6~C60의 아릴아민기, 핵원자수 5 내지 60의 헤테로아릴아민기 및 (C6~C60의 아릴)(핵원자수 5 내지 60의 헤테로아릴)아민기로 이루어진 군에서 선택되거나, 또는 인접하는 기와 축합하여 축합 고리를 형성하고, 구체적으로 수소, 중수소(D), 할로겐기, 시아노기, 니트로기, 아미노기, C1~C20의 알킬기, C2~C20의 알케닐기, C2~C20의 알키닐기, C3~C20의 시클로알킬기, 핵원자수 3 내지 20개의 헤테로시클로알킬기, C6~C30의 아릴기, 핵원자수 5 내지 30개의 헤테로아릴기, 및 C6~C30의 아릴아민기로 이루어진 군에서 선택될 수 있다.One or more R's are the same or different from each other, and are each independently hydrogen, deuterium (D), halogen group, cyano group, nitro group, amino group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~C 40 alkynyl group, C 3 ~C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 arylphosphine oxide group, C 6 ~ C 60 arylgermyl group, C 6 ~ C 60 arylamine group, nucleus It is selected from the group consisting of heteroarylamine groups having 5 to 60 atoms and (aryl of C 6 to C 60 ) (heteroaryl of 5 to 60 nuclear atoms) amine groups, or condensed with adjacent groups to form a condensed ring. , specifically hydrogen, deuterium (D), halogen group, cyano group, nitro group, amino group, C 1 ~ C 20 alkyl group, C 2 ~ C 20 alkenyl group, C 2 ~ C 20 alkynyl group, C 3 ~ In the group consisting of a C 20 cycloalkyl group, a heterocycloalkyl group with 3 to 20 nuclear atoms, a C 6 to C 30 aryl group, a heteroaryl group with 5 to 30 nuclear atoms, and an arylamine group with C 6 to C 30 can be selected.
상기 R의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기, 아릴게르밀기, 아릴아민기, 헤테로아릴아민기 및 (아릴)(헤테로아릴)아민기는, 각각 독립적으로 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환될 수 있다. 이때, 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이하다.The R alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl The phosphine group, arylphosphine oxide group, arylgermyl group, arylamine group, heteroarylamine group, and (aryl)(heteroaryl)amine group each independently contain deuterium (D), halogen, cyano group, nitro group, C 1 ~C 40 alkyl group, C 2 ~C 40 alkenyl group, C 2 ~C 40 alkynyl group, C 3 ~C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 ~C 60 Aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 alkylsilyl group, C 6 to C 60 Arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 arylphosphine oxide group and C 6 ~ C It may be substituted or unsubstituted with one or more substituents selected from the group consisting of 60 arylamine groups. At this time, when the substituents are plural, they are the same or different from each other.
상기 화학식 1로 표시되는 화합물에서, a, b, c, d, e 및 f는 각각 0 내지 3의 정수이고, 구체적으로 각각 0 또는 1일 수 있다.In the compound represented by Formula 1, a, b, c, d, e, and f are each integers from 0 to 3, and may specifically be 0 or 1, respectively.
여기서, a가 0인 경우, L1이 직접 결합(단일 결합)인 것을 의미하고, b가 0인 경우, L2가 직접 결합(단일 결합)인 것을 의미하며, c가 0인 경우, L3가 직접 결합(단일 결합)인 것을 의미하고, d가 0인 경우, L4가 직접 결합(단일 결합)인 것을 의미하며, e가 0인 경우, L5가 직접 결합(단일 결합)인 것을 의미하고, f가 0인 경우, L6가 직접 결합(단일 결합)인 것을 의미한다. 한편, a, b, c, d, e 및 f이 각각 1 내지 3의 정수인 경우, L1 내지 L6이 각각 2가의 링커기(linker)로, C6~C30의 아릴렌기, 핵원자수 5 내지 30의 헤테로아릴렌기 및 에테르기(-O-)로 이루어진 군에서 선택되고, 구체적으로 C6~C18의 아릴렌기, 핵원자수 5 내지 18의 헤테로아릴렌기 및 에테르기(-O-)로 이루어진 군에서 선택될 수 있다. 여기서, 복수의 L1 내지 복수의 L6는 서로 동일하거나 상이할 수 있다.Here, when a is 0, it means that L 1 is a direct bond (single bond), when b is 0, it means that L 2 is a direct bond (single bond), and when c is 0, it means that L 3 means that it is a direct bond (single bond), and when d is 0, it means that L 4 is a direct bond (single bond). If e is 0, it means that L 5 is a direct bond (single bond). And when f is 0, it means that L 6 is a direct bond (single bond). On the other hand, when a, b, c, d, e and f are each integers of 1 to 3, L 1 to L 6 are each divalent linker groups, C 6 to C 30 arylene groups, and the number of nuclear atoms. It is selected from the group consisting of a heteroarylene group having 5 to 30 atoms and an ether group (-O-), and specifically, an arylene group having C 6 to C 18 , a heteroarylene group having 5 to 18 nuclear atoms, and an ether group (-O- ) can be selected from the group consisting of Here, a plurality of L 1 to a plurality of L 6 may be the same or different from each other.
상기 L1 내지 L6의 아릴렌기 및 헤테로아릴렌기는 각각 독립적으로 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환될 수 있다. 이때, 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이하다.The arylene group and heteroarylene group of L 1 to L 6 are each independently selected from deuterium (D), halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C Substituted or unsubstituted with one or more substituents selected from the group consisting of 60 aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 arylphosphine oxide group, and C 6 ~ C 60 arylamine group It can be. At this time, when the substituents are plural, they are the same or different from each other.
일례에 따르면, L1 내지 L6은 서로 동일하거나 상이하고, 각각 독립적으로 직접 결합이거나, C6~C30의 아릴렌기이고, 상기 L1 내지 L6의 아릴렌기는 각각 독립적으로 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환될 수 있다. 이때, 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.According to one example, L 1 to L 6 are the same or different from each other, and are each independently a direct bond or an arylene group of C 6 to C 30 , and the arylene groups of L 1 to L 6 are each independently a deuterium (D) , halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, nuclear atoms 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of an arylphosphine oxide group and an arylamine group of C 6 to C 60 . At this time, when the substituents are plural, they may be the same or different from each other.
다른 일례에 따르면, L1 내지 L6은 서로 동일하거나 상이하고, 각각 독립적으로 직접 결합이거나, 페닐렌기, 비페닐렌기, 나프틸렌기, 안트라세닐렌기, 인데닐렌기, 피란트레닐렌기, 카르바졸릴렌기, 티오페닐렌기, 인돌일렌기, 푸리닐렌기, 퀴놀리닐렌기, 피롤일렌기, 이미다졸릴렌기, 옥사졸릴렌기, 티아졸릴렌기, 트리아졸릴렌기, 피리디닐렌기, 및 피리미디닐렌기로 이루어진 군에서 선택될 수 있다. 이때, 상기 페닐렌기, 비페닐렌기, 나프틸렌기, 안트라세닐렌기, 인데닐렌기, 피란트레닐렌기, 카르바졸릴렌기, 티오페닐렌기, 인돌일렌기, 푸리닐렌기, 퀴놀리닐렌기, 피롤일렌기, 이미다졸릴렌기, 옥사졸릴렌기, 티아졸릴렌기, 트리아졸릴렌기, 피리디닐렌기, 및 피리미디닐렌기는 각각 독립적으로 중수소(D), 할로겐, 시아노기, C1~C10의 알킬기, 핵원자수 5 내지 10의 헤테로아릴기로 이루어진 군에서 선택된 1 이상의 치환기로 치환되거나 비(非)-치환될 수 있다.According to another example, L 1 to L 6 are the same or different from each other, and are each independently a direct bond, or a phenylene group, a biphenylene group, a naphthylene group, an anthracenylene group, an indenylene group, a pyrantrenylene group, or a carboxylic acid group. Zolylene group, thiophenylene group, indolylene group, purinylene group, quinolinylene group, pyrrolylene group, imidazolylene group, oxazolylene group, thiazonylene group, triazonylene group, pyridinylene group, and pyrimidinylene group. It can be selected from a group consisting of: At this time, the phenylene group, biphenylene group, naphthylene group, anthracenylene group, indenylene group, pyrantrenylene group, carbazolylene group, thiophenylene group, indolylene group, purinylene group, quinolinylene group, p Rollylene group, imidazolylene group, oxazolilene group, thiazolilene group, triazolilene group, pyridinylene group, and pyrimidinylene group are each independently selected from deuterium (D), halogen, cyano group, C 1 to C 10 alkyl group, It may be substituted or unsubstituted with one or more substituents selected from the group consisting of heteroaryl groups having 5 to 10 nuclear atoms.
상기 L1 내지 L6에 따라, 상기 화학식 1로 표시되는 화합물은 하기 화학식 9 내지 15 중 어느 하나로 표시되는 화합물일 수 있는데, 이에 한정되지 않는다.Depending on L 1 to L 6 , the compound represented by Formula 1 may be a compound represented by any one of Formulas 9 to 15 below, but is not limited thereto.
Figure PCTKR2023021584-appb-img-000012
Figure PCTKR2023021584-appb-img-000012
Figure PCTKR2023021584-appb-img-000013
Figure PCTKR2023021584-appb-img-000013
Figure PCTKR2023021584-appb-img-000014
Figure PCTKR2023021584-appb-img-000014
Figure PCTKR2023021584-appb-img-000015
Figure PCTKR2023021584-appb-img-000015
Figure PCTKR2023021584-appb-img-000016
Figure PCTKR2023021584-appb-img-000016
Figure PCTKR2023021584-appb-img-000017
Figure PCTKR2023021584-appb-img-000017
Figure PCTKR2023021584-appb-img-000018
Figure PCTKR2023021584-appb-img-000018
상기 화학식 9 내지 15에서,In Formulas 9 to 15,
X1, A1 내지 A5, a, b, c, f, g, L1 내지 L3, L6, Ar1, Ar2, 및 R1 내지 R5는 각각 상기 화학식 1에 정의된 바와 같고,X 1 , A 1 to A 5 , a, b, c, f, g, L 1 to L 3 , L 6 , Ar 1 , Ar 2 , and R 1 to R 5 are each as defined in Formula 1 ,
n1 및 n2는 각각 0 내지 3의 정수이고,n1 and n2 are each integers from 0 to 3,
o 및 p는 각각 0 내지 4의 정수이며,o and p are each integers from 0 to 4,
복수의 R6 및 복수의 R7은 서로 동일하거나 상이하고, 각각 독립적으로 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택될 수 있다.A plurality of R 6 and a plurality of R 7 are the same or different from each other, and each independently represents deuterium (D), halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 ~C 40 alkyloxy group, C 6 ~C 60 aryloxy group, C 1 ~C 40 alkylsilyl group, C 6 ~C 60 arylsilyl group, C 1 ~C 40 alkyl boron group, C 6 It may be selected from the group consisting of a ~C 60 aryl boron group, a C 6 ~ C 60 arylphosphine group, a C 6 ~ C 60 arylphosphine oxide group, and a C 6 ~ C 60 arylamine group.
상기 화학식 1의 화합물에서, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소(D), 할로겐기, 시아노기, 니트로기, 아미노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, C6~C60의 아릴게르밀기, C6~C60의 아릴아민기, 핵원자수 5 내지 60의 헤테로아릴아민기, 및 (C6~C60의 아릴)(핵원자수 5 내지 60의 헤테로아릴)아민기로 이루어진 군에서 선택되거나, 또는 인접한 기와 서로 결합하여 축합 고리를 형성할 수 있다.In the compound of Formula 1, Ar 1 and Ar 2 are the same or different from each other, and are each independently hydrogen, deuterium (D), halogen group, cyano group, nitro group, amino group, C 1 to C 40 alkyl group, C 2 ~C 40 alkenyl group, C 2 ~C 40 alkynyl group, C 3 ~C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, 5 to 5 nuclear atoms 60 heteroaryl groups, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 arylphosphine oxide group, C 6 ~ C 60 arylgermyl group , C 6 ~C 60 arylamine group, heteroarylamine group with 5 to 60 nuclear atoms, and (C 6 to C 60 aryl) (heteroaryl with 5 to 60 nuclear atoms) amine group, or Adjacent groups can combine with each other to form a condensed ring.
이때, 상기 Ar1 및 Ar2의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기, 아릴게르밀기, 아릴아민기, 헤테로아릴아민기 및 (아릴)(헤테로아릴)아민기는, 각각 독립적으로 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환될 수 있다. 이때, 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이하다.At this time, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, and alkylboron group of Ar 1 and Ar 2 , aryl boron group, aryl phosphine group, aryl phosphine oxide group, aryl germyl group, aryl amine group, heteroaryl amine group, and (aryl) (heteroaryl) amine group are each independently deuterium (D), halogen, and cyano group. , nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, Aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C 1 to C 40 , aryloxy group of C 6 to C 60 , alkylsilyl group of C 1 to C 40 , C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 arylphosphine oxide It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups and C 6 to C 60 arylamine groups. At this time, when the substituents are plural, they are the same or different from each other.
상기 화학식 1로 표시되는 화합물에서, g는 0 내지 4의 정수이다. 여기서, g가 0인 경우, 수소가 치환기 R4로 비(非)-치환되는 것을 의미한다. 한편, g가 1 내지 4의 정수인 경우, 1개 또는 복수의 R4는 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소(D), 할로겐기, 시아노기, 니트로기, 아미노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, C6~C60의 아릴게르밀기, C6~C60의 아릴아민기, 핵원자수 5 내지 60의 헤테로아릴아민기 및 (C6~C60의 아릴)(핵원자수 5 내지 60의 헤테로아릴)아민기로 이루어진 군에서 선택되거나, 또는 인접하는 기와 축합하여 축합 고리를 형성할 수 있다. 여기서, 상기 헤테로시클로알킬기 및 헤테로아릴기는 각각 N, S, O, Ge, P, Sn 및 Se로 이루어진 군에서 선택된 1개 이상의 헤테로원자를 포함할 수 있고, 한편 상기 축합 고리는 C3~C60의 축합 지방족 고리(구체적으로, C3~C30의 축합 지방족 고리), C6~C60의 축합 방향족 고리(구체적으로, C6~C30의 축합 방향족 고리) 및 5원~60원의 축합 헤테로방향족고리(구체적으로, 5원~30원의 축합 헤테로방향족고리)로 이루어진 군에서 선택된 1종 이상일 수 있다. In the compound represented by Formula 1, g is an integer from 0 to 4. Here, when g is 0, it means that hydrogen is unsubstituted with a substituent R 4 . On the other hand, when g is an integer of 1 to 4, one or more R 4 are the same or different from each other, and are each independently hydrogen, deuterium (D), halogen group, cyano group, nitro group, amino group, C 1 to C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 ~ C 60 aryl group , heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphine group, C 6 to C 60 arylphosphine oxide group, C 6 to C 60 A group consisting of an arylgermyl group, an arylamine group of C 6 to C 60 , a heteroarylamine group of 5 to 60 nuclear atoms, and (aryl of C 6 to C 60 ) (heteroaryl of 5 to 60 nuclear atoms) amine group. It may be selected from or condensed with an adjacent group to form a condensed ring. Here, the heterocycloalkyl group and heteroaryl group may each include one or more heteroatoms selected from the group consisting of N, S, O, Ge, P, Sn, and Se, while the condensed ring has C 3 ~ C 60 A condensed aliphatic ring (specifically, a condensed aliphatic ring of C 3 to C 30 ), a fused aromatic ring of C 6 to C 60 (specifically, a fused aromatic ring of C 6 to C 30 ), and a 5- to 60-membered condensed ring. It may be one or more types selected from the group consisting of heteroaromatic rings (specifically, 5- to 30-membered condensed heteroaromatic rings).
구체적으로, 1개 또는 복수의 R4는 서로 동일하거나 상이하고, 각각 독립적으로 중수소(D), C1~C20의 알킬기, C6~C30의 아릴기 및 핵원자수 5 내지 30의 헤테로아릴기로 이루어진 군에서 선택되거나, 인접하는 기(예: R4-R3, R4-L3, R4-L1, R4-L4, R4-R1)와 결합하여 C3~C30의 축합 방향족 고리를 형성할 수 있고, 더 구체적으로 각각 독립적으로 C6~C30의 아릴기, 및 핵원자수 5 내지 30의 헤테로아릴기로 이루어진 군에서 선택되거나, 인접하는 기(예: R4-R3, R4-L3, R4-L1, R4-L4, R4-R1)와 결합하여 C3~C12의 축합 방향족 고리를 형성할 수 있다.Specifically, one or more R 4 are the same or different from each other, and each independently represents deuterium (D), an alkyl group of C 1 to C 20 , an aryl group of C 6 to C 30 and a hetero group of 5 to 30 nuclear atoms. selected from the group consisting of aryl groups, or adjacent groups (e.g. R 4 -R 3 , R 4 -L 3 , R 4 -L 1 , R 4 -L 4 , R 4 -R 1 ) can be combined to form a condensed aromatic ring of C 3 to C 30 , and more specifically, each independently an aryl group of C 6 to C 30 , and a heteroaryl group of 5 to 30 nuclear atoms. selected from the group consisting of or adjacent groups (e.g. R 4 -R 3 , R 4 -L 3 , R 4 -L 1 , R 4 -L 4 , It can be combined with R 4 -R 1 ) to form a condensed aromatic ring of C 3 to C 12 .
상기 화학식 1로 표시되는 화합물에서, R1 내지 R3, 및 R5는 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소(D), 할로겐기, 시아노기, 니트로기, 아미노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, C6~C60의 아릴게르밀기, C6~C60의 아릴아민기, 핵원자수 5 내지 60의 헤테로아릴아민기 및 (C6~C60의 아릴)(핵원자수 5 내지 60의 헤테로아릴)아민기로 이루어진 군에서 선택되거나, 또는 인접하는 기와 축합하여 축합 고리를 형성할 수 있다.In the compound represented by Formula 1, R 1 to R 3 and R 5 are the same or different from each other, and are each independently hydrogen, deuterium (D), halogen group, cyano group, nitro group, amino group, C 1 to C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 ~ C 60 aryl group , heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphine group, C 6 to C 60 arylphosphine oxide group, C 6 to C 60 A group consisting of an arylgermyl group, an arylamine group of C 6 to C 60 , a heteroarylamine group of 5 to 60 nuclear atoms, and (aryl of C 6 to C 60 ) (heteroaryl of 5 to 60 nuclear atoms) amine group. It may be selected from or condensed with an adjacent group to form a condensed ring.
구체적으로, R1 내지 R3, 및 R5는 서로 동일하거나 상이하고, 각각 독립적으로 중수소(D), C1~C20의 알킬기, C6~C30의 아릴기, 핵원자수 5 내지 30의 헤테로아릴기, C6~C60의 아릴실릴기, C6~C60의 아릴포스핀옥사이드기, C6~C60의 아릴게르밀기로 이루어진 군에서 선택되거나, 인접하는 기(예: R1-L1, R1-R4, R2-L2, R2-R4, R3-L3, R3-R4, R5-L6)와 결합하여 C3~C30의 축합 방향족 고리 및 핵원자수 5 내지 30의 축합 헤테로방향족 고리를 형성할 수 있고, 더 구체적으로 각각 독립적으로 C6~C30의 아릴기, 및 핵원자수 5 내지 30의 헤테로아릴기로 이루어진 군에서 선택되거나, 인접하는 기(예: R1-L1, R1-R4, R2-L2, R2-R4, R3-L3, R3-R4, R5-L6)와 결합하여 C3~C12의 축합 방향족 고리 및 핵원자수 5 내지 18의 축합 헤테로방향족 고리를 형성할 수 있다.Specifically, R 1 to R 3 and R 5 are the same or different from each other, and each independently represents deuterium (D), a C 1 to C 20 alkyl group, a C 6 to C 30 aryl group, and 5 to 30 nuclear atoms. selected from the group consisting of heteroaryl group, C 6 ~ C 60 arylsilyl group, C 6 ~ C 60 arylphosphine oxide group, C 6 ~ C 60 arylgermyl group, or an adjacent group (e.g. R 1 -L 1 , R 1 -R 4 , R 2 -L 2 , R 2 -R 4 , R 3 -L 3 , R 3 -R 4 , R 5 -L 6 ) in combination with C 3 ~C 30 It can form a condensed aromatic ring and a condensed heteroaromatic ring having 5 to 30 nuclear atoms, and more specifically, each independently from the group consisting of an aryl group of C 6 to C 30 and a heteroaryl group of 5 to 30 nuclear atoms. Selected or adjacent groups (e.g. R 1 -L 1 , R 1 -R 4 , R 2 -L 2 , R 2 -R 4 , R 3 -L 3 , R 3 -R 4 , R 5 -L 6 ) can be combined with a C 3 to C 12 condensed aromatic ring and a condensed heteroaromatic ring having 5 to 18 nuclear atoms.
상기 R1 내지 R5의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기, 아릴게르밀기, 아릴아민기, 헤테로아릴아민기 및 (아릴)(헤테로아릴)아민기는, 각각 독립적으로 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이하다.The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, aryl group of R 1 to R 5 The boron group, arylphosphine group, arylphosphine oxide group, arylgermyl group, arylamine group, heteroarylamine group, and (aryl)(heteroaryl)amine group are each independently deuterium (D), halogen, cyano group, and nitro group. group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 ~C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 alkylsilyl group, C 6 ~C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 arylphosphine oxide group, and It is substituted or unsubstituted with one or more substituents selected from the group consisting of C 6 to C 60 arylamine groups, wherein when the substituents are plural, they are the same or different from each other.
일례에 따르면, 상기 R5는 수소, 중수소(D), 할로겐기, 시아노기, 및 하기 화학식 B1 내지 B25로 표시되는 치환체로 이루어진 군에서 선택된 것일 수 있다:According to one example, R 5 may be selected from the group consisting of hydrogen, deuterium (D), halogen group, cyano group, and substituents represented by the following formulas B1 to B25:
Figure PCTKR2023021584-appb-img-000019
Figure PCTKR2023021584-appb-img-000019
Figure PCTKR2023021584-appb-img-000020
Figure PCTKR2023021584-appb-img-000020
상기 화학식 B1 내지 B25에서, In the above formulas B1 to B25,
a1은 0 내지 5의 정수이고,a1 is an integer from 0 to 5,
a2는 0 내지 4의 정수이며,a2 is an integer from 0 to 4,
a3는 0 내지 3의 정수이고,a3 is an integer from 0 to 3,
a4는 0 내지 7의 정수이며,a4 is an integer from 0 to 7,
a5는 0 내지 9의 정수이고,a5 is an integer from 0 to 9,
a6는 0 내지 2의 정수이고,a6 is an integer from 0 to 2,
W1 및 W2는 서로 동일하거나 상이하고, 각각 독립적으로 S, O, Si(R10)(R11), 및 C(R12)(R13)로 이루어진 군에서 선택되고,W 1 and W 2 are the same as or different from each other, and are each independently selected from the group consisting of S, O, Si(R 10 )(R 11 ), and C(R 12 )(R 13 ),
W3는 S, O, Si(R14)(R15), C(R16)(R17) 및 N(R18)로 이루어진 군에서 선택되고,W 3 is selected from the group consisting of S, O, Si(R 14 )(R 15 ), C(R 16 )(R 17 ) and N(R 18 ),
W4는 Si, Ge 또는 C이며,W 4 is Si, Ge or C,
W5는 S 또는 O이고,W 5 is S or O,
환 Cy1은 C6~C18의 축합 방향족환 또는 핵원자수 5~21개의 축합 헤테로방향족환이고,Ring Cy1 is a fused aromatic ring of C 6 to C 18 or a fused heteroaromatic ring of 5 to 21 nuclear atoms,
복수의 R8은 서로 동일하거나 상이하고,A plurality of R 8 is the same or different from each other,
R8 내지 R18은 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소(D), 할로겐기, 시아노기, 니트로기, 아미노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 또는 인접하는 기와 축합하여 축합 고리를 형성하고,R 8 to R 18 are the same or different from each other, and are each independently hydrogen, deuterium (D), halogen group, cyano group, nitro group, amino group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 arylphosphine oxide group, and C 6 ~ C 60 arylamine group selected from the group consisting of, or an adjacent group Condensates to form a condensed ring,
상기 R8 내지 R18의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는, 각각 독립적으로 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이하다.The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, aryl group of R 8 to R 18 The boron group, arylphosphine group, arylphosphine oxide group, and arylamine group each independently contain deuterium (D), halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C Substituted with one or more substituents selected from the group consisting of an aryl boron group of 6 to C 60 , an arylphosphine group of C 6 to C 60 , an arylphosphine oxide group of C 6 to C 60 , and an arylamine group of C 6 to C 60 or unsubstituted, and in this case, when the substituents are plural, they are the same or different from each other.
전술한 본 발명에 따른 화학식 1로 표시되는 화합물은 하기 화합물 1 내지 150 중 어느 하나로 구체화될 수 있다. 그러나, 본 발명에 따른 화학식 1로 표시되는 화합물이 하기 예시된 것에 의해 한정되는 것은 아니다.The compound represented by Formula 1 according to the present invention described above may be embodied as any one of the following compounds 1 to 150. However, the compound represented by Formula 1 according to the present invention is not limited to the examples below.
Figure PCTKR2023021584-appb-img-000021
Figure PCTKR2023021584-appb-img-000021
Figure PCTKR2023021584-appb-img-000022
Figure PCTKR2023021584-appb-img-000022
Figure PCTKR2023021584-appb-img-000023
Figure PCTKR2023021584-appb-img-000023
Figure PCTKR2023021584-appb-img-000024
Figure PCTKR2023021584-appb-img-000024
Figure PCTKR2023021584-appb-img-000025
Figure PCTKR2023021584-appb-img-000025
본 발명에서 "알킬"은 탄소수 1 내지 40의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등이 있는데, 이에 한정되지는 않는다.In the present invention, “alkyl” refers to a monovalent substituent derived from a straight-chain or branched-chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, and hexyl.
본 발명에서 "알케닐(alkenyl)"은 탄소-탄소 이중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등이 있는데, 이에 한정되지는 않는다.In the present invention, “alkenyl” refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include vinyl, allyl, isopropenyl, 2-butenyl, etc., but are not limited thereto.
본 발명에서 "알키닐(alkynyl)"은 탄소-탄소 삼중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등이 있는데, 이에 한정되지는 않는다.In the present invention, “alkynyl” refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon triple bonds. Examples thereof include ethynyl, 2-propynyl, etc., but are not limited thereto.
본 발명에서 "시클로알킬"은 탄소수 3 내지 40의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이러한 사이클로알킬의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 노르보닐(norbornyl), 아다만틴(adamantine) 등이 있는데, 이에 한정되지는 않는다.In the present invention, “cycloalkyl” refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.
본 발명에서 "헤테로시클로알킬"은 핵원자수 3 내지 40의 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S, Ge, P, Sn 또는 Se와 같은 헤테로 원자로 치환된다. 이러한 헤테로시클로알킬의 예로는 모르폴린, 피페라진 등이 있는데, 이에 한정되지는 않는다.In the present invention, “heterocycloalkyl” refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon, preferably 1 to 3 carbons in the ring, is N, O, S , is substituted with a heteroatom such as Ge, P, Sn or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine.
본 발명에서 "아릴"은 단독 고리 또는 2이상의 고리가 조합된 탄소수 6 내지 60의 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있다. 이러한 아릴의 예로는 페닐, 나프틸, 페난트릴, 안트릴 등이 있는데, 이에 한정되지는 않는다.In the present invention, “aryl” refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, either a single ring or a combination of two or more rings. In addition, a form in which two or more rings are simply attached to each other (pendant) or condensed may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.
본 발명에서 "헤테로아릴"은 핵원자수 5 내지 60의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이때, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S, Ge, P, Sn 또는 Se와 같은 헤테로원자로 치환된다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있고, 나아가 아릴기와의축합된 형태도 포함될 수 있다. 이러한 헤테로아릴의 예로는 피리딜, 피라지닐, 피리미디닐, 피리다지닐, 트리아지닐과 같은 6-원 모노사이클릭 고리, 페녹사티에닐(phenoxathienyl), 인돌리지닐(indolizinyl), 인돌릴(indolyl), 퓨리닐(purinyl), 퀴놀릴(quinolyl), 벤조티아졸(benzothiazole), 카바졸릴(carbazolyl)과 같은 폴리사이클릭 고리 및 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등이 있는데, 이에 한정되지는 않는다.In the present invention, “heteroaryl” refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon, preferably 1 to 3 carbons, of the ring is replaced with a heteroatom such as N, O, S, Ge, P, Sn or Se. In addition, a form in which two or more rings are simply pendant or condensed with each other may be included, and a form in which two or more rings are condensed with an aryl group may also be included. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, phenoxathienyl, indolizinyl, and indolyl ( Polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, etc., but are not limited thereto.
본 발명에서 "알킬옥시"는 R'O-로 표시되는 1가의 치환기로, 상기 R'는 탄소수 1 내지 40의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함할 수 있다. 이러한 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등이 있는데, 이에 한정되지는 않는다.In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, where R' refers to alkyl having 1 to 40 carbon atoms and has a linear, branched, or cyclic structure. may include. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.
본 발명에서 "아릴옥시"는 RO-로 표시되는 1가의 치환기로, 상기 R은 탄소수 5 내지 40의 아릴을 의미한다. 이러한 아릴옥시의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등이 있는데, 이에 한정되지는 않는다.In the present invention, “aryloxy” is a monovalent substituent represented by RO-, where R refers to aryl having 5 to 40 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, etc., but are not limited thereto.
본 발명에서 "알킬실릴"은 탄소수 1 내지 40의 알킬로 치환된 실릴을 의미하며, 모노-뿐만 아니라 디-, 트리-알킬실릴을 포함한다. 또, "아릴실릴"은 탄소수 5 내지 60의 아릴로 치환된 실릴을 의미하고, 모노-뿐만 아니라 디-, 트리-아릴실릴 등의 폴리아릴실릴을 포함한다.In the present invention, “alkylsilyl” refers to silyl substituted with alkyl having 1 to 40 carbon atoms, and includes not only mono-, but also di- and tri-alkylsilyl. In addition, “arylsilyl” refers to silyl substituted with aryl having 5 to 60 carbon atoms, and includes polyarylsilyl such as mono-, di-, and tri-arylsilyl.
본 발명에서 "알킬보론기"는 탄소수 1 내지 40의 알킬로 치환된 보론기를 의미하며, "아릴보론기"는 탄소수 6 내지 60의 아릴로 치환된 보론기를 의미한다.In the present invention, “alkyl boron group” refers to a boron group substituted with alkyl having 1 to 40 carbon atoms, and “aryl boron group” refers to a boron group substituted with aryl having 6 to 60 carbon atoms.
본 발명에서 "알킬포스피닐기"는 탄소수 1 내지 40의 알킬로 치환된 포스핀기를 의미하고, 모노- 뿐만 아니라 디-알킬포스피닐기를 포함한다. 또, 본 발명에서 "아릴포스피닐기"는 탄소수 6 내지 60의 모노아릴 또는 디아릴로 치환된 포스핀기를 의미하고, 모노- 뿐만 아니라 디-아릴포스피닐기를 포함한다. In the present invention, “alkylphosphinyl group” refers to a phosphine group substituted with alkyl having 1 to 40 carbon atoms, and includes mono- as well as di-alkylphosphinyl groups. Additionally, in the present invention, “arylphosphinyl group” refers to a phosphine group substituted with monoaryl or diaryl having 6 to 60 carbon atoms, and includes not only mono- but also di-arylphosphinyl groups.
본 발명에서 "아릴아민"은 탄소수 6 내지 60의 아릴로 치환된 아민을 의미하며, 모노-뿐만 아니라 디-아릴아민를 포함한다.In the present invention, “arylamine” refers to an amine substituted with aryl having 6 to 60 carbon atoms, and includes mono- as well as di-arylamine.
본 발명에서 "헤테로아릴아민"은 핵원자수 5 내지 60의헤테로아릴로 치환된 아민을 의미하며, 모노-뿐만 아니라 디-헤테로아릴아민를 포함한다.In the present invention, “heteroarylamine” refers to an amine substituted with heteroaryl having 5 to 60 nuclear atoms, and includes mono- as well as di-heteroarylamine.
본발명에서 (아릴)(헤테로아릴)아민은 탄소수 6 내지 60의 아릴 및 핵원자수 5 내지 60의헤테로아릴로 치환된 아민을 의미한다.In the present invention, (aryl)(heteroaryl)amine refers to an amine substituted with aryl having 6 to 60 carbon atoms and heteroaryl having 5 to 60 nuclear atoms.
본 발명에서 "축합고리"는 탄소수 3 내지 40의 축합지방족 고리, 탄소수 6 내지 60의 축합 방향족 고리, 핵원자수 3 내지 60의축합헤테로지방족 고리, 핵원자수 5 내지 60의축합헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다.In the present invention, "condensed ring" refers to a condensed aliphatic ring having 3 to 40 carbon atoms, a fused aromatic ring having 6 to 60 carbon atoms, a fused heteroaliphatic ring having 3 to 60 nuclear atoms, a fused heteroaromatic ring having 5 to 60 nuclear atoms, or It refers to a combination of these forms.
본 발명에서, "핵원자수"는 고리(환) 구조를 구성하는 고리 원자의 수를 의미하는 것으로, 상기 핵원자는 탄소이거나 또는 N, O, S 및 Se로 이루어진 군에서 선택된 헤테로원자를 의미할 수 있다. 일례로, 피리딘의 핵원자수는 피리딘 고리를 구성하는 5개의 C와 1개의 N를 포함하여 6개를 의미한다.In the present invention, “nuclear atom number” refers to the number of ring atoms constituting a ring structure, and the nuclear atom refers to carbon or a heteroatom selected from the group consisting of N, O, S, and Se. can do. For example, the number of nuclear atoms of pyridine is 6, including 5 C and 1 N that make up the pyridine ring.
<유기 전계 발광 소자><Organic electroluminescent device>
한편, 본 발명은 전술한 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자(이하, '유기 EL 소자')를 제공한다.Meanwhile, the present invention provides an organic electroluminescent device (hereinafter referred to as 'organic EL device') containing the compound represented by the above-mentioned formula (1).
구체적으로, 본 발명에 따른 유기 전계 발광 소자는 도 1 내지 도 3에 도시된 바와 같이, 애노드(anode)(100), 캐소드(cathode)(200) 및 상기 애노드와 캐소드 사이에 개재(介在)된 1층 이상의 유기물층(300)을 포함하며, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함한다. 이때, 상기 화합물은 단독으로 사용되거나, 또는 2 이상이 혼합되어 사용될 수 있다.Specifically, the organic electroluminescent device according to the present invention, as shown in FIGS. 1 to 3, includes an anode 100, a cathode 200, and an electroluminescent device interposed between the anode and the cathode. It includes one or more organic layers 300, and at least one of the one or more organic layers includes the compound represented by Chemical Formula 1. At this time, the above compounds may be used alone, or two or more may be used in combination.
상기 1층 이상의 유기물층(300)은 정공 주입층(310), 정공 수송층(320), 발광층(330), 전자 수송층(340), 및 전자 주입층(350) 중 어느 하나 이상을 포함할 수 있고, 선택적으로 전자 수송 보조층(360)을 추가적으로 더 포함할 수 있다. 이때, 적어도 하나의 유기물층(300)은 상기 화학식 1로 표시되는 화합물을 포함한다. 구체적으로, 상기 화학식 1의 화합물을 포함하는 유기물층은 전자수송층(340) 또는 전자수송 보조층(360)일 수 있다.The one or more organic layer 300 may include one or more of a hole injection layer 310, a hole transport layer 320, a light emitting layer 330, an electron transport layer 340, and an electron injection layer 350, Optionally, an auxiliary electron transport layer 360 may be additionally included. At this time, at least one organic material layer 300 includes the compound represented by Formula 1 above. Specifically, the organic material layer containing the compound of Formula 1 may be the electron transport layer 340 or the electron transport auxiliary layer 360.
일례에 따르면, 상기 1층 이상의 유기물층은 정공주입층, 정공수송층, 발광층, 전자수송층, 및 전자주입층을 포함하고, 선택적으로 전자수송보조층을 더 포함할 수 있다. 상기 전자 수송층은 상기 화학식 1로 표시되는 화합물을 포함한다. 이때, 상기 화학식 1로 표시되는 화합물은 전자수송층 물질로 유기 전계 발광 소자에 포함된다. 이러한 유기 전계 발광 소자에서, 전자는 상기 화학식 1의 화합물 때문에, 캐소드 또는 전자주입층에서 전자수송층으로 용이하게 주입되고, 또한 전자수송층에서 발광층으로 빠르게 이동할 수 있어, 발광층에서의 정공과 전자의 결합력이 높다. 그러므로, 본 발명의 유기 전계 발광 소자는 발광효율, 전력효율, 휘도 등이 우수하다. 게다가, 상기 화학식 1의 화합물은 열적 안정성, 전기화학적 안정성이 우수하여, 유기 전계 발광 소자의 성능을 향상시킬 수 있다. According to one example, the one or more organic material layers include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, and may optionally further include an electron transport auxiliary layer. The electron transport layer includes the compound represented by Formula 1 above. At this time, the compound represented by Formula 1 is included in the organic electroluminescent device as an electron transport layer material. In this organic electroluminescent device, electrons are easily injected from the cathode or the electron injection layer into the electron transport layer due to the compound of Formula 1, and can also quickly move from the electron transport layer to the light-emitting layer, so that the bonding force between holes and electrons in the light-emitting layer is increased. high. Therefore, the organic electroluminescent device of the present invention has excellent luminous efficiency, power efficiency, brightness, etc. In addition, the compound of Formula 1 has excellent thermal and electrochemical stability, and can improve the performance of organic electroluminescent devices.
이와 같은 화학식 1의 화합물은 단독으로 사용되거나, 또는 당 분야에 공지된 전자수송층 재료와 혼용될 수 있다.The compound of Formula 1 may be used alone or mixed with electron transport layer materials known in the art.
본 발명에서 상기 화학식 1의 화합물과 혼용될 수 있는 전자수송층 재료는 당 분야에서 통상적으로 공지된 전자수송 물질을 포함한다. 사용 가능한 전자 수송 물질의 비제한적인 예로는 옥사졸계 화합물, 이소옥사졸계 화합물, 트리아졸계 화합물, 이소티아졸(isothiazole)계 화합물, 옥사디아졸계 화합물, 티아다아졸(thiadiazole)계 화합물, 페릴렌(perylene)계 화합물, 알루미늄 착물(예: Alq3, tris(8-quinolinolato)-aluminium), 갈륨착물(예: Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)) 등이 있다. 이들을 단독으로 사용하거나 또는 2종 이상 혼용할 수 있다. In the present invention, electron transport layer materials that can be used interchangeably with the compound of Formula 1 include electron transport materials commonly known in the art. Non-limiting examples of usable electron transport materials include oxazole-based compounds, isoxazole-based compounds, triazole-based compounds, isothiazole-based compounds, oxadiazole-based compounds, thiadiazole-based compounds, perylene ( perylene)-based compounds, aluminum complexes (e.g. Alq 3, tris(8-quinolinolato)-aluminium), gallium complexes (e.g. Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)), etc. These can be used alone or two or more types can be used together.
본 발명에서, 상기 화학식 1의 화합물과 전자수송층 재료를 혼용할 경우, 이들의 혼합 비율은 특별히 제한되지 않으며, 당 분야에 공지된 범위 내에서 적절히 조절될 수 있다. In the present invention, when the compound of Formula 1 and the electron transport layer material are mixed, their mixing ratio is not particularly limited and can be appropriately adjusted within a range known in the art.
다른 일례에 따르면, 상기 1층 이상의 유기물층은 정공주입층, 정공수송층, 발광층, 전자수송 보조층, 전자수송층, 및 전자주입층을 포함하고, 상기 전자수송 보조층은 상기 화학식 1로 표시되는 화합물을 포함한다. 이때, 상기 화학식 1로 표시되는 화합물은 전자수송 보조층 물질로 유기 전계 발광 소자에 포함된다. 상기 화학식 1로 표시되는 화합물은 높은 삼중항 에너지를 갖는다. 이 때문에, 상기 화학식 1의 화합물을 전자수송 보조층 물질로 포함할 경우, TTF(triplet-triplet fusion) 효과로 인해 유기 전계 발광 소자의 효율이 상승될 수 있다. 또한, 상기 화학식 1의 화합물은 발광층에서 생성된 엑시톤이나 정공이 발광층에 인접하는 전자수송층으로 확산되는 것을 방지할 수 있다. 따라서, 발광층 내에서 발광에 기여하는 엑시톤의 수가 증가되어 소자의 발광 효율이 개선될 수 있고, 소자의 내구성 및 안정성이 향상되어 소자의 수명이 효율적으로 증가될 수 있다. According to another example, the one or more organic material layers include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer, and the electron transport auxiliary layer includes the compound represented by Formula 1. Includes. At this time, the compound represented by Formula 1 is included in the organic electroluminescent device as an electron transport auxiliary layer material. The compound represented by Formula 1 has high triplet energy. For this reason, when the compound of Formula 1 is included as an electron transport auxiliary layer material, the efficiency of the organic electroluminescent device can be increased due to the triplet-triplet fusion (TTF) effect. Additionally, the compound of Formula 1 can prevent excitons or holes generated in the light-emitting layer from diffusing into the electron transport layer adjacent to the light-emitting layer. Accordingly, the number of excitons contributing to light emission in the light-emitting layer can be increased to improve the light-emitting efficiency of the device, and the durability and stability of the device can be improved to effectively increase the lifespan of the device.
이와 같은 화학식 1의 화합물은 단독으로 사용되거나, 또는 당 분야에 공지된 전자수송층 보조층 재료와 혼용될 수 있다.The compound of Formula 1 may be used alone or mixed with materials for the electron transport layer auxiliary layer known in the art.
본 발명에서 상기 화학식 1의 화합물과 혼용될 수 있는 전자수송 보조층 재료로는 당 분야에서 통상적으로 공지된 전자수송 물질을 포함하며, 예컨대 옥사디아졸 유도체, 트리아졸 유도체, 페난트롤린 유도체(예, BCP), 질소를 포함하는 헤테로환 유도체 등이 있는데, 이에 한정되지 않는다.In the present invention, the electron transport auxiliary layer material that can be mixed with the compound of Formula 1 includes electron transport materials commonly known in the art, such as oxadiazole derivatives, triazole derivatives, and phenanthroline derivatives (e.g. , BCP), heterocyclic derivatives containing nitrogen, etc., but are not limited thereto.
전술한 본 발명의 유기 전계 발광 소자의 구조는 특별히 한정되지 않으나, 예컨대 기판 위에, 애노드(100), 1층 이상의 유기물층(300) 및 캐소드(200)가 순차적으로 적층될 수 있다(도 1 내지 도 3 참조). 뿐만 아니라, 도시되지 않았지만, 전극과 유기물층 계면에 절연층 또는 접착층이 삽입된 구조일 수 있다.The structure of the organic electroluminescent device of the present invention described above is not particularly limited, but for example, the anode 100, one or more organic layer 300, and cathode 200 may be sequentially stacked on a substrate (FIGS. 1 to 1) 3). In addition, although not shown, it may have a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer.
일례에 따르면, 유기 전계 발광 소자는 도 1에 도시된 바와 같이, 기판 위에, 애노드(100), 정공주입층(310), 정공수송층(320), 발광층(330), 전자수송층(340) 및 캐소드(200)가 순차적으로 적층된 구조를 가질 수 있다. 선택적으로, 도 2에 도시된 바와 같이, 상기 전자수송층(340)과 캐소드(200) 사이에 전자주입층(350)이 위치할 수 있다. 또, 상기 발광층(330)과 전자수송층(340) 사이에 전자수송 보조층(360)이 위치할 수 있다(도 3 참조). According to one example, as shown in FIG. 1, the organic electroluminescent device includes an anode 100, a hole injection layer 310, a hole transport layer 320, a light emitting layer 330, an electron transport layer 340, and a cathode on a substrate. (200) may have a sequentially stacked structure. Optionally, as shown in FIG. 2, an electron injection layer 350 may be positioned between the electron transport layer 340 and the cathode 200. Additionally, an auxiliary electron transport layer 360 may be located between the light emitting layer 330 and the electron transport layer 340 (see FIG. 3).
본 발명의 유기 전계 발광 소자는 상기 유기물층(300) 중 적어도 하나[예, 전자수송층(340) 또는 전자수송 보조층(360)]가 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는, 당 기술 분야에 알려져 있는 재료 및 방법으로 유기물층 및 전극을 형성하여 제조할 수 있다.The organic electroluminescent device of the present invention contains a It can be manufactured by forming an organic material layer and an electrode using materials and methods known in the technical field.
상기 유기물층은 진공 증착법이나 용액 도포법에 의하여 형성될 수 있다. 상기 용액 도포법의 예로는 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이에 한정되지는 않는다.The organic material layer may be formed by vacuum deposition or solution application. Examples of the solution application method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
본 발명에서 사용 가능한 기판은 특별히 한정되지 않으며, 비제한적인 예로는 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 및 시트 등이 있다.The substrate that can be used in the present invention is not particularly limited, and non-limiting examples include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets.
또, 애노드 물질의 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연산화물, 인듐산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리티오펜, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 또는 폴리아닐린과 같은 전도성 고분자; 및 카본블랙 등이 있는데, 이에 한정되지는 않는다.Additionally, examples of anode materials include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; Conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black, but are not limited thereto.
또, 캐소드 물질의 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은(Ag), 주석, 또는 납과 같은 금속 또는 이들의 합금; 및 LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있는데, 이에 한정되지는 않는다.Additionally, examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver (Ag), tin, or lead, or alloys thereof; and multilayer structure materials such as LiF/Al or LiO 2 /Al, etc., but are not limited thereto.
또한, 정공주입층, 정공수송층, 발광층 및 전자 주입층은 특별히 한정되는 것은 아니며, 당 업계에 알려진 통상의 물질을 사용할 수 있다.Additionally, the hole injection layer, hole transport layer, light emitting layer, and electron injection layer are not particularly limited, and common materials known in the art can be used.
이하 본 발명을 실시예를 통하여 상세히 설명하면 다음과 같다. 단, 하기 실시예는 본 발명을 예시하는 것일 뿐, 본 발명이 하기 실시예에 의해 한정되는 것은 아니다.Hereinafter, the present invention will be described in detail through examples. However, the following examples are merely illustrative of the present invention, and the present invention is not limited by the following examples.
[준비예 1] 화합물 J-1의 합성[Preparation Example 1] Synthesis of Compound J-1
Figure PCTKR2023021584-appb-img-000026
Figure PCTKR2023021584-appb-img-000026
triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-(3-bromo-5-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (4.22 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), 및 K2CO3 (2.76 g, 20 mmol)를 1,4-Dioxane 100 ml/ H2O 25 ml에 넣고 100℃에서 8시간 동안 교반하였다. 반응 종결 후, 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하여 유기층을 얻었다. 여과된 유기층의 용매를 제거한 후, 컬럼크로마토그래피를 이용하여 목적 화합물 J-1 (3.39 g, 수율 50 %)을 얻었다.triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-(3-bromo-5-chlorophenyl)- 4,6-diphenyl-1,3,5-triazine (4.22 g, 10 mmol), Pd(PPh 3 ) 4 (0.34 g, 0.3 mmol), and K 2 CO 3 (2.76 g, 20 mmol) in 1, 100 ml of 4-Dioxane/25 ml of H 2 O was added and stirred at 100°C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO 4 was added and filtered to obtain an organic layer. After removing the solvent in the filtered organic layer, the target compound J-1 (3.39 g, yield 50%) was obtained using column chromatography.
[준비예 2] 화합물 J-2의 합성[Preparation Example 2] Synthesis of Compound J-2
Figure PCTKR2023021584-appb-img-000027
Figure PCTKR2023021584-appb-img-000027
triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-(4-bromo-3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (4.22 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), 및 K2CO3 (2.76 g, 20 mmol)를 1,4-Dioxane 100 ml/ H2O 25 ml에 넣고 100℃에서 8시간 동안 교반하였다. 반응 종결 후, 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하여 유기층을 얻었다. 여과된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 J-2 (3.32 g, 수율 49 %)을 얻었다.triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-(4-bromo-3-chlorophenyl)- 4,6-diphenyl-1,3,5-triazine (4.22 g, 10 mmol), Pd(PPh 3 ) 4 (0.34 g, 0.3 mmol), and K 2 CO 3 (2.76 g, 20 mmol) in 1, 100 ml of 4-Dioxane/25 ml of H 2 O was added and stirred at 100°C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO 4 was added and filtered to obtain an organic layer. After removing the solvent in the filtered organic layer, the target compound J-2 (3.32 g, yield 49%) was obtained using column chromatography.
[준비예 3] 화합물 J-3의 합성[Preparation Example 3] Synthesis of Compound J-3
Figure PCTKR2023021584-appb-img-000028
Figure PCTKR2023021584-appb-img-000028
triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-(3-bromo-4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (4.22 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), 및 K2CO3 (2.76 g, 20 mmol)를 1,4-Dioxane 100 ml/ H2O 25 ml에 넣고 100℃에서 8시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하여 유기층을 얻었다. 여과된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 J-3 (3.25 g, 수율 48 %)을 얻었다.triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-(3-bromo-4-chlorophenyl)- 4,6-diphenyl-1,3,5-triazine (4.22 g, 10 mmol), Pd(PPh 3 ) 4 (0.34 g, 0.3 mmol), and K 2 CO 3 (2.76 g, 20 mmol) in 1, 100 ml of 4-Dioxane/25 ml of H 2 O was added and stirred at 100°C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO 4 was added and filtered to obtain an organic layer. After removing the solvent in the filtered organic layer, the target compound J-3 (3.25 g, yield 48%) was obtained using column chromatography.
[준비예 4] 화합물 J-4의 합성[Preparation Example 4] Synthesis of Compound J-4
Figure PCTKR2023021584-appb-img-000029
Figure PCTKR2023021584-appb-img-000029
triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-(2-bromo-5-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (4.22 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), 및 K2CO3 (2.76 g, 20 mmol)를 1,4-Dioxane 100 ml/ H2O 25 ml에 넣고 100℃에서 8시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하여 유기층을 얻었다. 여과된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 J-4 (3.18 g, 수율 47 %)을 얻었다.triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-(2-bromo-5-chlorophenyl)- 4,6-diphenyl-1,3,5-triazine (4.22 g, 10 mmol), Pd(PPh 3 ) 4 (0.34 g, 0.3 mmol), and K 2 CO 3 (2.76 g, 20 mmol) in 1, 100 ml of 4-Dioxane/25 ml of H 2 O was added and stirred at 100°C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO 4 was added and filtered to obtain an organic layer. After removing the solvent in the filtered organic layer, the target compound J-4 (3.18 g, yield 47%) was obtained using column chromatography.
[준비예 5] 화합물 J-5의 합성[Preparation Example 5] Synthesis of Compound J-5
Figure PCTKR2023021584-appb-img-000030
Figure PCTKR2023021584-appb-img-000030
triphenyl(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-(3-bromo-5-chlorophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (5.12 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), 및 K2CO3 (2.76 g, 20 mmol)를 1,4-Dioxane 100 ml/ H2O 25 ml에 넣고 100℃에서 8시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하여 유기층을 얻었다. 여과된 유기층의 용매를 제거한 후, 컬럼크로마토그래피를 이용하여 목적 화합물 J-5 (3.53 g, 수율 46 %)을 얻었다.triphenyl(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-(3-bromo-5-chlorophenyl)- 4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (5.12 g, 10 mmol), Pd(PPh 3 ) 4 (0.34 g, 0.3 mmol), and K 2 CO 3 (2.76 g, 20 mmol) was added to 100 ml of 1,4-Dioxane/25 ml of H 2 O and stirred at 100°C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO 4 was added and filtered to obtain an organic layer. After removing the solvent in the filtered organic layer, the target compound J-5 (3.53 g, yield 46%) was obtained using column chromatography.
[준비예 6] 화합물 J-6의 합성[Preparation Example 6] Synthesis of Compound J-6
Figure PCTKR2023021584-appb-img-000031
Figure PCTKR2023021584-appb-img-000031
triphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-([1,1'-biphenyl]-4-yl)-4-(3-bromo-5-chlorophenyl)-6-phenyl-1,3,5-triazine (4.98 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), 및 K2CO3 (2.76 g, 20 mmol)를 1,4-Dioxane 100 ml/ H2O 25 ml에 넣고 100℃에서 8시간 동안 교반하였다. 반응 종결 후, 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하여 유기층을 얻었다. 여과된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 J-6 (3.39 g, 수율 45 %)을 얻었다.triphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-([1,1'-biphenyl]- 4-yl)-4-(3-bromo-5-chlorophenyl)-6-phenyl-1,3,5-triazine (4.98 g, 10 mmol), Pd(PPh 3 ) 4 (0.34 g, 0.3 mmol), and K 2 CO 3 (2.76 g, 20 mmol) were added to 100 ml of 1,4-Dioxane/25 ml of H 2 O and stirred at 100°C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO 4 was added and filtered to obtain an organic layer. After removing the solvent in the filtered organic layer, the target compound J-6 (3.39 g, yield 45%) was obtained using column chromatography.
[준비예 7] 화합물 J-7의 합성[Preparation Example 7] Synthesis of Compound J-7
Figure PCTKR2023021584-appb-img-000032
Figure PCTKR2023021584-appb-img-000032
dimethyl(phenyl)(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (3.38 g, 10 mmol), 2-(3-bromo-5-chlorophenyl)-4,6-bis(dibenzo[b,d]furan-2-yl)-1,3,5-triazine (6.02 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), 및 K2CO3 (2.76 g, 20 mmol)를 1,4-Dioxane 100 ml/ H2O 25 ml에 넣고 100℃에서 8시간 동안 교반하였다. 반응 종결 후, 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하여 유기층을 얻었다. 여과된 유기층의 용매를 제거한 후, 컬럼크로마토그래피를 이용하여 목적 화합물 J-7 (3.52 g, 수율 48 %)을 얻었다.dimethyl(phenyl)(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (3.38 g, 10 mmol), 2-(3-bromo-5- chlorophenyl)-4,6-bis(dibenzo[b,d]furan-2-yl)-1,3,5-triazine (6.02 g, 10 mmol), Pd(PPh 3 ) 4 (0.34 g, 0.3 mmol) , and K 2 CO 3 (2.76 g, 20 mmol) were added to 100 ml of 1,4-Dioxane/25 ml of H 2 O and stirred at 100°C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO 4 was added and filtered to obtain an organic layer. After removing the solvent in the filtered organic layer, the target compound J-7 (3.52 g, yield 48%) was obtained using column chromatography.
[준비예 8] 화합물 J-8의 합성[Preparation Example 8] Synthesis of Compound J-8
Figure PCTKR2023021584-appb-img-000033
Figure PCTKR2023021584-appb-img-000033
trimethyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (2.76 g, 10 mmol), 2-(3-bromo-5-chlorophenyl)-4-(naphthalen-1-yl)-6-(6-phenyldibenzo[b,d]thiophen-4-yl)-1,3,5-triazine (6.55 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), K2CO3 (2.76 g, 20 mmol)를 1,4-Dioxane 100 ml/ H2O 25 ml에 넣고 100℃에서 8시간 동안 교반하였다. 반응 종결 후, 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하여 유기층을 얻었다. 여과된 유기층의 용매를 제거한 후, 컬럼크로마토그래피를 이용하여 목적 화합물 J-8 (3.54 g, 수율 49 %)을 얻었다.trimethyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (2.76 g, 10 mmol), 2-(3-bromo-5-chlorophenyl)- 4-(naphthalen-1-yl)-6-(6-phenyldibenzo[b,d]thiophen-4-yl)-1,3,5-triazine (6.55 g, 10 mmol), Pd(PPh 3 ) 4 ( 0.34 g, 0.3 mmol) and K 2 CO 3 (2.76 g, 20 mmol) were added to 100 ml of 1,4-Dioxane/25 ml of H 2 O and stirred at 100°C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO 4 was added and filtered to obtain an organic layer. After removing the solvent in the filtered organic layer, the target compound J-8 (3.54 g, yield 49%) was obtained using column chromatography.
[준비예 9] 화합물 J-9 의 합성[Preparation Example 9] Synthesis of Compound J-9
Figure PCTKR2023021584-appb-img-000034
Figure PCTKR2023021584-appb-img-000034
(4-(tert-butyl)phenyl)diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (5.18 g, 10 mmol), 2-(3-bromo-4-chlorophenyl)-4-(4-(dibenzo[b,e][1,4]dioxin-1-yl)phenyl)-6-phenyl-1,3,5-triazine (6.04 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), 및 K2CO3 (2.76 g, 20 mmol)를 1,4-Dioxane 100 ml/ H2O 25 ml에 넣고 100℃에서 8시간 동안 교반하였다. 반응 종결 후, 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하여 유기층을 얻었다. 여과된 유기층의 용매를 제거한 후, 컬럼크로마토그래피를 이용하여 목적 화합물 J-9 (4.58 g, 수율 50 %)을 얻었다.(4-(tert-butyl)phenyl)diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (5.18 g, 10 mmol), 2- (3-bromo-4-chlorophenyl)-4-(4-(dibenzo[b,e][1,4]dioxin-1-yl)phenyl)-6-phenyl-1,3,5-triazine (6.04 g , 10 mmol), Pd(PPh 3 ) 4 (0.34 g, 0.3 mmol), and K 2 CO 3 (2.76 g, 20 mmol) were added to 100 ml of 1,4-Dioxane/25 ml of H 2 O and incubated at 100°C. It was stirred for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO 4 was added and filtered to obtain an organic layer. After removing the solvent in the filtered organic layer, the target compound J-9 (4.58 g, yield 50%) was obtained using column chromatography.
[준비예 10] 화합물 J-10의 합성[Preparation Example 10] Synthesis of Compound J-10
Figure PCTKR2023021584-appb-img-000035
Figure PCTKR2023021584-appb-img-000035
triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)germane (5.07 g, 10 mmol), 2-(3-bromo-5-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (4.22 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), 및 K2CO3 (2.76 g, 20 mmol)를 1,4-Dioxane 100 ml/ H2O 25 ml에 넣고 100℃에서 8시간 동안 교반하였다. 반응 종결 후, 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하여 유기층을 얻었다. 여과된 유기층의 용매를 제거한 후, 컬럼크로마토그래피를 이용하여 목적 화합물 J-10 (3.61 g, 수율 50 %)을 얻었다.triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)germane (5.07 g, 10 mmol), 2-(3-bromo-5-chlorophenyl)- 4,6-diphenyl-1,3,5-triazine (4.22 g, 10 mmol), Pd(PPh 3 ) 4 (0.34 g, 0.3 mmol), and K 2 CO 3 (2.76 g, 20 mmol) in 1, 100 ml of 4-Dioxane/25 ml of H 2 O was added and stirred at 100°C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO 4 was added and filtered to obtain an organic layer. After removing the solvent in the filtered organic layer, the target compound J-10 (3.61 g, yield 50%) was obtained using column chromatography.
[합성예 1] 화합물 1의 합성[Synthesis Example 1] Synthesis of Compound 1
Figure PCTKR2023021584-appb-img-000036
Figure PCTKR2023021584-appb-img-000036
준비예 1에서 합성된 화합물 J-1 (6.78 g, 10 mmol), triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), 및 Cs2CO3 (6.51 g, 20 mmol)를 1,4-Dioxane 100 ml/H2O 25 ml에 넣고, 100℃에서 8시간 동안 교반하였다. 반응 종결 후, 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하여 유기층을 얻었다. 여과된 유기층의 용매를 제거한 후, 컬럼크로마토그래피를 이용하여 화합물 1 (4.01 g, 수율 41 %)을 얻었다.Compound J-1 (6.78 g, 10 mmol) synthesized in Preparation Example 1, triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), Pd(OAc) 2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and Cs 2 CO 3 (6.51 g, 20 mmol) in 100 ml of 1,4-Dioxane /H 2 O was added to 25 ml and stirred at 100°C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO 4 was added and filtered to obtain an organic layer. After removing the solvent in the filtered organic layer, Compound 1 (4.01 g, yield 41%) was obtained using column chromatography.
Mass : [(M+H)+] : 978Mass : [(M+H) + ] : 978
[합성예 2] 화합물 2의 합성[Synthesis Example 2] Synthesis of Compound 2
Figure PCTKR2023021584-appb-img-000037
Figure PCTKR2023021584-appb-img-000037
준비예 2에서 합성된 화합물 J-2 (6.78 g, 10 mmol), triphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), 및 Cs2CO3 (6.51 g, 20 mmol)를 1,4-Dioxane 100 ml/H2O 25 ml에 넣고, 100℃에서 8시간 동안 교반하였다. 반응 종결 후, 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하여 유기층을 얻었다. 여과된 유기층의 용매를 제거한 후, 컬럼크로마토그래피를 이용하여 화합물 2 (4.10 g, 수율 42 %)을 얻었다.Compound J-2 (6.78 g, 10 mmol) synthesized in Preparation Example 2, triphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), Pd(OAc) 2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and Cs 2 CO 3 (6.51 g, 20 mmol) in 100 ml of 1,4-Dioxane /H 2 O was added to 25 ml and stirred at 100°C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO 4 was added and filtered to obtain an organic layer. After removing the solvent in the filtered organic layer, Compound 2 (4.10 g, yield 42%) was obtained using column chromatography.
Mass : [(M+H)+] : 978Mass : [(M+H) + ] : 978
[합성예 3] 화합물 3의 합성[Synthesis Example 3] Synthesis of Compound 3
Figure PCTKR2023021584-appb-img-000038
Figure PCTKR2023021584-appb-img-000038
준비예 3에서 합성된 화합물 J-3 (6.78 g, 10 mmol), 5,5-diphenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5H-dibenzo[b,d]silole (4.60 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), 및 Cs2CO3 (6.51 g, 20 mmol)를 1,4-Dioxane 100 ml/H2O 25 ml에 넣고, 100℃에서 8시간 동안 교반하였다. 반응 종결 후, 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하여 유기층을 얻었다. 여과된 유기층의 용매를 제거한 후, 컬럼크로마토그래피를 이용하여 화합물 3 (4.19 g, 수율 43 %)을 얻었다.Compound J-3 (6.78 g, 10 mmol), 5,5-diphenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- synthesized in Preparation Example 3 5H-dibenzo[b,d]silole (4.60 g, 10 mmol), Pd(OAc) 2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and Cs 2 CO 3 (6.51 g, 20 mmol) was added to 100 ml of 1,4-Dioxane/25 ml of H 2 O, and stirred at 100°C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO 4 was added and filtered to obtain an organic layer. After removing the solvent in the filtered organic layer, Compound 3 (4.19 g, yield 43%) was obtained using column chromatography.
Mass : [(M+H)+] : 976Mass : [(M+H) + ] : 976
[합성예 4] 화합물 4의 합성[Synthesis Example 4] Synthesis of Compound 4
Figure PCTKR2023021584-appb-img-000039
Figure PCTKR2023021584-appb-img-000039
준비예 4에서 합성된 화합물 J-4 (6.78 g, 10 mmol), 5,5-dimethyl-3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5H-dibenzo[b,d]silole (4.12 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), 및 Cs2CO3 (6.51 g, 20 mmol)를 1,4-Dioxane 100 ml/H2O 25 ml에 넣고 100℃에서 8시간 동안 교반하였다. 반응 종결 후, 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하여 유기층을 얻었다. 여과된 유기층의 용매를 제거한 후, 컬럼크로마토그래피를 이용하여 화합물 4 (4.08 g, 수율 44 %)을 얻었다.Compound J-4 (6.78 g, 10 mmol), 5,5-dimethyl-3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-) synthesized in Preparation Example 4 yl)phenyl)-5H-dibenzo[b,d]silole (4.12 g, 10 mmol), Pd(OAc) 2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and Cs 2 CO 3 (6.51 g, 20 mmol) was added to 100 ml of 1,4-Dioxane/25 ml of H 2 O and stirred at 100°C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO 4 was added and filtered to obtain an organic layer. After removing the solvent in the filtered organic layer, Compound 4 (4.08 g, yield 44%) was obtained using column chromatography.
Mass : [(M+H)+] : 928Mass : [(M+H) + ] : 928
[합성예 5] 화합물 5의 합성[Synthesis Example 5] Synthesis of Compound 5
Figure PCTKR2023021584-appb-img-000040
Figure PCTKR2023021584-appb-img-000040
준비예 5에서 합성된 화합물 J-5 (7.68 g, 10 mmol), 10,10-dimethyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-dibenzo[b,e][1,4]oxasiline (3.52 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), 및 Cs2CO3 (6.51 g, 20 mmol)를 1,4-Dioxane 100 ml/H2O 25 ml에 넣고, 100℃에서 8시간 동안 교반하였다. 반응 종결 후, 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하여 유기층을 얻었다. 여과된 유기층의 용매를 제거한 후, 컬럼크로마토그래피를 이용하여 화합물 5 (4.31 g, 수율 45 %)을 얻었다.Compound J-5 (7.68 g, 10 mmol), 10,10-dimethyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- synthesized in Preparation Example 5 10H-dibenzo[b,e][1,4]oxasiline (3.52 g, 10 mmol), Pd(OAc) 2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and Cs 2 CO 3 (6.51 g, 20 mmol) was added to 100 ml of 1,4-Dioxane/25 ml of H 2 O, and stirred at 100°C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO 4 was added and filtered to obtain an organic layer. After removing the solvent in the filtered organic layer, Compound 5 (4.31 g, yield 45%) was obtained using column chromatography.
Mass : [(M+H)+] : 958Mass : [(M+H) + ] : 958
[합성예 6] 화합물 6의 합성[Synthesis Example 6] Synthesis of Compound 6
Figure PCTKR2023021584-appb-img-000041
Figure PCTKR2023021584-appb-img-000041
준비예 6에서 합성된 화합물 J-6 (7.54 g, 10 mmol), 2-(dibenzo[b,d]furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.94 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs2CO3 (6.51 g, 20 mmol)를 1,4-Dioxane 100 ml/H2O 25 ml에 넣고, 100℃에서 8시간 동안 교반하였다. 반응 종결 후, 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하여 유기층을 얻었다. 여과된 유기층의 용매를 제거한 후, 컬럼크로마토그래피를 이용하여 화합물 6 (4.07 g, 수율 46 %)을 얻었다.Compound J-6 (7.54 g, 10 mmol), 2-(dibenzo[b,d]furan-3-yl)-4,4,5,5-tetramethyl-1,3,2- synthesized in Preparation Example 6 dioxaborolane (2.94 g, 10 mmol), Pd(OAc) 2 ( 0.22 g, 1 mmol) , 100 ml/H 2 O was added to 25 ml and stirred at 100°C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO 4 was added and filtered to obtain an organic layer. After removing the solvent in the filtered organic layer, Compound 6 (4.07 g, yield 46%) was obtained using column chromatography.
Mass : [(M+H)+] : 886Mass : [(M+H) + ] : 886
[합성예 7] 화합물 7의 합성[Synthesis Example 7] Synthesis of Compound 7
Figure PCTKR2023021584-appb-img-000042
Figure PCTKR2023021584-appb-img-000042
준비예 7에서 합성된 화합물 J-7 (7.34 g, 10 mmol), 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (3.69 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), 및 Cs2CO3 (6.51 g, 20 mmol)를 1,4-Dioxane 100 ml/H2O 25 ml에 넣고 100℃에서 8시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하여 유기층을 얻었다. 여과된 유기층의 용매를 제거한 후, 컬럼크로마토그래피를 이용하여 화합물 7 (4.51 g, 수율 48 %)을 얻었다.Compound J-7 (7.34 g, 10 mmol), 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H- synthesized in Preparation Example 7 carbazole (3.69 g, 10 mmol), Pd(OAc) 2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and Cs 2 CO 3 (6.51 g, 20 mmol) Dioxane 100 ml/H 2 O was added to 25 ml and stirred at 100°C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO 4 was added and filtered to obtain an organic layer. After removing the solvent in the filtered organic layer, Compound 7 (4.51 g, yield 48%) was obtained using column chromatography.
Mass : [(M+H)+] : 941Mass : [(M+H) + ] : 941
[합성예 8] 화합물 8의 합성[Synthesis Example 8] Synthesis of Compound 8
Figure PCTKR2023021584-appb-img-000043
Figure PCTKR2023021584-appb-img-000043
준비예 8에서 합성된 화합물 J-8 (7.24 g, 10 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (4.35 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), 및 Cs2CO3 (6.51 g, 20 mmol)를 1,4-Dioxane 100 ml/H2O 25 ml에 넣고, 100℃에서 8시간 동안 교반하였다. 반응 종결 후, 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하여 유기층을 얻었다. 여과된 유기층의 용매를 제거한 후, 컬럼크로마토그래피를 이용하여 화합물 8 (4.88 g, 수율 49 %)을 얻었다.Compound J-8 (7.24 g, 10 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-) synthesized in Preparation Example 8 yl)phenyl)-1,3,5-triazine (4.35 g, 10 mmol), Pd(OAc) 2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and Cs 2 CO 3 ( 6.51 g, 20 mmol) was added to 100 ml of 1,4-Dioxane/25 ml of H 2 O, and stirred at 100°C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO 4 was added and filtered to obtain an organic layer. After removing the solvent in the filtered organic layer, Compound 8 (4.88 g, yield 49%) was obtained using column chromatography.
Mass : [(M+H)+] : 997Mass : [(M+H) + ] : 997
[합성예 9] 화합물 9의 합성[Synthesis Example 9] Synthesis of Compound 9
Figure PCTKR2023021584-appb-img-000044
Figure PCTKR2023021584-appb-img-000044
준비예 9에서 합성된 화합물 J-9 (9.16 g, 10 mmol), 4,4,5,5-tetramethyl-2-(6-phenyldibenzo[b,d]thiophen-4-yl)-1,3,2-dioxaborolane (3.86 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), 및 Cs2CO3 (6.51 g, 20 mmol)를 1,4-Dioxane 100 ml/H2O 25 ml에 넣고, 100℃에서 8시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하여 유기층을 얻었다. 여과된 유기층의 용매를 제거한 후, 컬럼크로마토그래피를 이용하여 화합물 9 (5.70 g, 수율 50 %)을 얻었다.Compound J-9 (9.16 g, 10 mmol), 4,4,5,5-tetramethyl-2-(6-phenyldibenzo[b,d]thiophen-4-yl)-1,3, synthesized in Preparation Example 9, 2-dioxaborolane (3.86 g, 10 mmol), Pd(OAc) 2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and Cs 2 CO 3 (6.51 g, 20 mmol) 4-Dioxane 100 ml/H 2 O was added to 25 ml and stirred at 100°C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO 4 was added and filtered to obtain an organic layer. After removing the solvent in the filtered organic layer, compound 9 (5.70 g, yield 50%) was obtained using column chromatography.
Mass : [(M+H)+] : 1140Mass : [(M+H) + ] : 1140
[합성예 10] 화합물 10의 합성[Synthesis Example 10] Synthesis of Compound 10
Figure PCTKR2023021584-appb-img-000045
Figure PCTKR2023021584-appb-img-000045
준비예 10에서 합성된 화합물 J-10 (7.22 g, 10 mmol), 4,4,5,5-tetramethyl-2-(spiro[fluorene-9,9'-xanthen]-2-yl)-1,3,2-dioxaborolane (4.58 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), 및 Cs2CO3 (6.51 g, 20 mmol)를 1,4-Dioxane 100 ml/H2O 25 ml에 넣고 100℃에서 8시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하여 유기층을 얻었다. 여과된 유기층의 용매를 제거한 후, 컬럼크로마토그래피를 이용하여 화합물 10 (5.09 g, 수율 50 %)을 얻었다.Compound J-10 (7.22 g, 10 mmol), 4,4,5,5-tetramethyl-2-(spiro[fluorene-9,9'-xanthen]-2-yl)-1, synthesized in Preparation Example 10, 3,2-dioxaborolane (4.58 g, 10 mmol), Pd(OAc) 2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and Cs 2 CO 3 (6.51 g, 20 mmol) 1,4-Dioxane 100 ml/H 2 O was added to 25 ml and stirred at 100°C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO 4 was added and filtered to obtain an organic layer. After removing the solvent in the filtered organic layer, Compound 10 (5.09 g, yield 50%) was obtained using column chromatography.
Mass : [(M+H)+] : 1018Mass : [(M+H) + ] : 1018
[합성예 11] 화합물 121의 합성[Synthesis Example 11] Synthesis of Compound 121
Figure PCTKR2023021584-appb-img-000046
Figure PCTKR2023021584-appb-img-000046
triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-(4''-chloro-[1,1':2',1''-terphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine (4.96 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), 및 Cs2CO3 (6.51 g, 20 mmol)를 1,4-Dioxane 100 ml/H2O 25 ml에 넣고 100℃에서 8시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하여 유기층을 얻었다. 여과된 유기층의 용매를 제거한 후, 컬럼크로마토그래피를 이용하여 화합물 121 (3.26 g, 수율 41 %)을 얻었다.triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-(4''-chloro-[1, 1':2',1''-terphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine (4.96 g, 10 mmol), Pd(OAc) 2 (0.22 g, 1 mmol) ) , ​ After completion of the reaction, extraction was performed with methylene chloride, MgSO 4 was added and filtered to obtain an organic layer. After removing the solvent in the filtered organic layer, compound 121 (3.26 g, yield 41%) was obtained using column chromatography.
Mass : [(M+H)+] : 796Mass : [(M+H) + ] : 796
[합성예 12] 화합물 122의 합성[Synthesis Example 12] Synthesis of Compound 122
Figure PCTKR2023021584-appb-img-000047
Figure PCTKR2023021584-appb-img-000047
triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-(5-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (5.09 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), 및 Cs2CO3 (6.51 g, 20 mmol)를 1,4-Dioxane 100 ml/H2O 25 ml에 넣고 100℃에서 8시간 동안 교반하였다. 반응 종결 후, 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하여 유기층을 얻었다. 여과된 유기층의 용매를 제거한 후, 컬럼크로마토그래피를 이용하여 화합물 122 (3.40 g, 수율 42 %)을 얻었다.triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-(5-chloro-[1,1' -biphenyl]-3-yl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (5.09 g, 10 mmol), Pd(OAc) 2 ( 0.22 g , 1 mmol ) , Stirred for an hour. After completion of the reaction, extraction was performed with methylene chloride, MgSO 4 was added and filtered to obtain an organic layer. After removing the solvent in the filtered organic layer, compound 122 (3.40 g, yield 42%) was obtained using column chromatography.
Mass : [(M+H)+] : 810Mass : [(M+H) + ] : 810
[합성예 13] 화합물 123의 합성[Synthesis Example 13] Synthesis of Compound 123
Figure PCTKR2023021584-appb-img-000048
Figure PCTKR2023021584-appb-img-000048
triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-(3''-chloro-[1,1':3',1''-terphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (4.96 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), 및 Cs2CO3 (6.51 g, 20 mmol)를 1,4-Dioxane 100 ml/H2O 25 ml에 넣고 100℃에서 8시간 동안 교반하였다. 반응 종결 후, 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하여 유기층을 얻었다. 여과된 유기층의 용매를 제거한 후, 컬럼크로마토그래피를 이용하여 화합물 123 (3.42 g, 수율 43 %)을 얻었다.triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-(3''-chloro-[1, 1':3',1''-terphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (4.96 g, 10 mmol), Pd(OAc) 2 (0.22 g, 1 mmol) ) , ​ After completion of the reaction, extraction was performed with methylene chloride, MgSO 4 was added and filtered to obtain an organic layer. After removing the solvent in the filtered organic layer, compound 123 (3.42 g, yield 43%) was obtained using column chromatography.
Mass : [(M+H)+] : 796Mass : [(M+H) + ] : 796
[실시예 1 내지 13] 청색 유기 전계 발광 소자의 제작[Examples 1 to 13] Fabrication of blue organic electroluminescent device
상기 합성예 1 내지 13에서 각각 합성된 화합물을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후, 아래의 과정에 따라 청색 유기 전계 발광 소자를 제작하였다.After purifying the compounds synthesized in Synthesis Examples 1 to 13 to high purity by sublimation purification by a commonly known method, a blue organic electroluminescent device was manufactured according to the process below.
먼저, ITO (Indium tin oxide)가 1200 Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면, 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후, UV OZONE 세정기(Power sonic 405, 화신테크)로 이송시킨 다음, UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, a glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1200 Å was washed with distilled water ultrasonic waves. After cleaning with distilled water, ultrasonic cleaning with solvents such as isopropyl alcohol, acetone, and methanol, drying, transferring to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then cleaning the substrate for 5 minutes using UV. and transferred the substrate to a vacuum evaporator.
상기와 같이 준비된 ITO 투명 전극 위에, HI + 2% HAT-CN6 (10 nm)/HI(140 nm)/EB (5 nm)/BH + 2 % BD (20nm)/표 1의 전자 수송 보조층 재료 (5 nm)/ET + Liq (1:1)(30 nm)/LiF (1 nm)/Al (100 nm) 순으로 적층하여 유기 전계 발광 소자를 제조하였다. 이때, 사용된 HI, HAT-CN6, EB, BH, BD, ET, Liq의 구조는 각각 하기와 같다.On the ITO transparent electrode prepared as above, HI + 2% HAT-CN6 (10 nm)/HI (140 nm)/EB (5 nm)/BH + 2% BD (20nm)/electron transport auxiliary layer material in Table 1 An organic electroluminescent device was manufactured by stacking in the following order: (5 nm)/ET + Liq (1:1)(30 nm)/LiF (1 nm)/Al (100 nm). At this time, the structures of HI, HAT-CN6, EB, BH, BD, ET, and Liq used are respectively as follows.
Figure PCTKR2023021584-appb-img-000049
Figure PCTKR2023021584-appb-img-000049
[비교예 1 내지 3] 청색 유기 전계 발광 소자의 제조[Comparative Examples 1 to 3] Preparation of blue organic electroluminescent device
전자 수송 보조층 재료로서 화합물 1 대신 하기 화합물 HB1, HB2 및 HB3을 각각 사용하는 것을 제외하고는, 상기 실시예 1과 동일하게 수행하여 청색 유기 전계 발광 소자를 제작하였다. 이때 사용된 HB1, HB2 및 HB3의 구조는 하기와 같다.A blue organic electroluminescent device was manufactured in the same manner as Example 1, except that the following compounds HB1, HB2, and HB3 were used instead of Compound 1 as the electron transport auxiliary layer material. The structures of HB1, HB2, and HB3 used at this time are as follows.
Figure PCTKR2023021584-appb-img-000050
Figure PCTKR2023021584-appb-img-000051
Figure PCTKR2023021584-appb-img-000050
Figure PCTKR2023021584-appb-img-000051
[평가예 1][Evaluation Example 1]
실시예 1 내지 13 및 비교예 1 내지 3에서 각각 제조된 유기 전계 발광 소자에 대하여, 전류밀도 10 mA/㎠에서의 구동전압, 발광파장, 전류효율을 측정하였고, 그 결과를 하기 표 1에 나타내었다.For the organic electroluminescent devices prepared in Examples 1 to 13 and Comparative Examples 1 to 3, the driving voltage, emission wavelength, and current efficiency were measured at a current density of 10 mA/cm2, and the results are shown in Table 1 below. It was.
샘플Sample 전자수송 보조층 재료Electron transport auxiliary layer material 구동 전압(V)Driving voltage (V) 발광 피크(nm)Emission peak (nm) 전류효율(cd/A)Current efficiency (cd/A)
실시예 1Example 1 1One 4.04.0 454454 7.97.9
실시예 2Example 2 22 4.94.9 455455 6.16.1
실시예 3Example 3 33 4.54.5 456456 6.06.0
실시예 4Example 4 44 4.94.9 459459 6.96.9
실시예 5Example 5 55 4.14.1 452452 6.16.1
실시예 6Example 6 66 4.24.2 454454 6.36.3
실시예 7Example 7 77 5.05.0 455455 7.57.5
실시예 8Example 8 88 5.15.1 458458 7.27.2
실시예 9Example 9 99 4.94.9 452452 6.16.1
실시예 10Example 10 1010 4.94.9 459459 7.07.0
실시예 11Example 11 121121 4.04.0 455455 6.96.9
실시예 12Example 12 122122 4.14.1 456456 6.86.8
실시예 13Example 13 123123 4.24.2 457457 6.66.6
비교예 1Comparative Example 1 HB1HB1 5.15.1 458458 5.95.9
비교예 2Comparative Example 2 HB2HB2 5.25.2 454454 5.55.5
비교예 3Comparative Example 3 HB3HB3 5.45.4 452452 5.15.1
상기 표 1로부터 실시예 1 내지 13에서 제조된 유기 발광 소자는 각각 비교예 1 내지 3에서 제조된 유기 발광 소자의 구동전압, 발광피크 및 전류효율에 비하여 우수하다는 것을 확인할 수 있었다.From Table 1, it was confirmed that the organic light-emitting devices manufactured in Examples 1 to 13 were superior to the driving voltage, emission peak, and current efficiency of the organic light-emitting devices manufactured in Comparative Examples 1 to 3, respectively.

Claims (8)

  1. 하기 화학식 1로 표시되는 화합물:Compound represented by Formula 1:
    [화학식 1][Formula 1]
    Figure PCTKR2023021584-appb-img-000052
    Figure PCTKR2023021584-appb-img-000052
    (상기 화학식 1에서,(In Formula 1 above,
    X1은 C, Si, Ge 또는 Sn이고,X 1 is C, Si, Ge or Sn,
    A1 내지 A5는 각각 N 또는 CR이고, A 1 to A 5 are each N or CR,
    다만 A1 내지 A5 중 적어도 하나는 CR이고, 이때 N이 아닌 CR 중 하나는 L4와 연결되고, However, at least one of A 1 to A 5 is CR, and in this case, one of the CRs other than N is connected to L 4 ,
    복수의 R은 서로 동일하거나 상이하며,A plurality of R is the same or different from each other,
    a, b, c, d, e 및 f는 각각 0 내지 3의 정수이고,a, b, c, d, e and f are each integers from 0 to 3,
    g는 0 내지 4의 정수이며g is an integer from 0 to 4
    L1 내지 L6는 서로 동일하거나 상이하고, 각각 독립적으로 직접 결합이거나, 또는 C6~C30의 아릴렌기, 핵원자수 5 내지 30개의 헤테로아릴렌기 및 에테르기(-O-)로 이루어진 군에서 선택되고,L 1 to L 6 are the same or different from each other, and are each independently a direct bond, or a group consisting of an arylene group of C 6 to C 30 , a heteroarylene group of 5 to 30 nuclear atoms, and an ether group (-O-) is selected from,
    R 및 R1 내지 R5는 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소(D), 할로겐기, 시아노기, 니트로기, 아미노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, C6~C60의 아릴게르밀기, C6~C60의 아릴아민기, 핵원자수 5 내지 60의 헤테로아릴아민기 및 (C6~C60의 아릴)(핵원자수 5 내지 60의 헤테로아릴)아민기로 이루어진 군에서 선택되거나, 또는 인접하는 기와 축합하여 축합 고리를 형성하고,R and R 1 to R 5 are the same or different from each other, and are each independently hydrogen, deuterium (D), halogen group, cyano group, nitro group, amino group, C 1 to C 40 alkyl group, C 2 to C 40 alkene. Nyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms. , C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group , C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 arylphosphine oxide group, C 6 ~ C 60 arylgermyl group, C 6 ~ C 60 aryl Selected from the group consisting of an amine group, a heteroarylamine group having 5 to 60 nuclear atoms, and (aryl of C 6 to C 60 ) (heteroaryl of 5 to 60 nuclear atoms) amine group, or condensed by condensation with an adjacent group. forming a ring,
    Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소(D), 할로겐기, 시아노기, 니트로기, 아미노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, C6~C60의 아릴게르밀기, C6~C60의 아릴아민기, 핵원자수 5 내지 60의 헤테로아릴아민기, 및 (C6~C60의 아릴)(핵원자수 5 내지 60의 헤테로아릴)아민기로 이루어진 군에서 선택되거나, 또는 인접한 기와 서로 결합하여 축합 고리를 형성할 수 있고;Ar 1 and Ar 2 are the same as or different from each other, and are each independently hydrogen, deuterium (D), halogen group, cyano group, nitro group, amino group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 arylphosphine oxide group, C 6 ~ C 60 arylgermyl group, C 6 ~ C 60 arylamine group , heteroarylamine group having 5 to 60 nuclear atoms, and (C 6 to C 60 aryl) (heteroaryl having 5 to 60 nuclear atoms) amine group, or bonded to adjacent groups to form a condensed ring. can form;
    상기 L1 내지 L6의 아릴렌기 및 헤테로아릴렌기와, 상기 R, R1 내지 R5와 Ar1 및 Ar2의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기, 아릴게르밀기, 아릴아민기, 헤테로아릴아민기 및 (아릴)(헤테로아릴)아민기는, 각각 독립적으로 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이함).The arylene group and heteroarylene group of L 1 to L 6 , the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl of R, R 1 to R 5 and Ar 1 and Ar 2 group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylgermyl group, arylamine group, heteroarylamine group and ( Aryl) (heteroaryl) amine group each independently represents deuterium (D), halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, and C 2 to C 40 alkynyl group. , C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group. , C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group , C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 arylphosphine oxide group, and C 6 ~ C 60 arylamine group. In this case, the substituent is substituted or unsubstituted with one or more types of substituents selected from the group consisting of If is plural, they are the same or different from each other).
  2. 제1항에 있어서,According to paragraph 1,
    상기 화학식 1로 표시되는 화합물은 하기 화학식 2 내지 4 중 어느 하나로 표시되는 것인, 화합물:The compound represented by Formula 1 is represented by any one of the following Formulas 2 to 4:
    [화학식 2][Formula 2]
    Figure PCTKR2023021584-appb-img-000053
    Figure PCTKR2023021584-appb-img-000053
    [화학식 3][Formula 3]
    Figure PCTKR2023021584-appb-img-000054
    Figure PCTKR2023021584-appb-img-000054
    [화학식 4][Formula 4]
    Figure PCTKR2023021584-appb-img-000055
    Figure PCTKR2023021584-appb-img-000055
    [화학식 5][Formula 5]
    Figure PCTKR2023021584-appb-img-000056
    Figure PCTKR2023021584-appb-img-000056
    [화학식 6][Formula 6]
    Figure PCTKR2023021584-appb-img-000057
    Figure PCTKR2023021584-appb-img-000057
    [화학식 7][Formula 7]
    Figure PCTKR2023021584-appb-img-000058
    Figure PCTKR2023021584-appb-img-000058
    [화학식 8][Formula 8]
    Figure PCTKR2023021584-appb-img-000059
    Figure PCTKR2023021584-appb-img-000059
    (상기 화학식 2 내지 8에서,(In Formulas 2 to 8,
    X1, A1 내지 A5, a, b, c, d, e, f, g, L1 내지 L6, Ar1, Ar2, 및 R1 내지 R5는 각각 제1항에 정의된 바와 같음).X 1 , A 1 to A 5 , a, b, c, d, e, f, g, L 1 to L 6 , Ar 1 , Ar 2 , and R 1 to R 5 are each as defined in claim 1. equivalence).
  3. 제1항에 있어서,According to paragraph 1,
    L1 내지 L6은 서로 동일하거나 상이하고, 각각 독립적으로 직접 결합이거나, C6~C30의 아릴렌기이고, L 1 to L 6 are the same or different from each other, and are each independently a direct bond or an arylene group of C 6 to C 30 ,
    상기 L1 내지 L6의 아릴렌기는 각각 독립적으로 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이한 것인, 화합물.The arylene groups of L 1 to L 6 are each independently selected from deuterium (D), halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkyl group. Nyl group, C 3 to C 40 cycloalkyl group, C 3 to C 40 heterocycloalkyl group, C 6 to C 60 aryl group, 5 to 60 nuclear atoms heteroaryl group, C 1 to C 40 alkyl group. Period, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 arylphosphine oxide group, and C 6 ~ C 60 arylamine group, wherein the above is substituted or unsubstituted with one or more types of substituents selected from the group consisting of When there are multiple substituents, they are the same or different from each other.
  4. 제1항에 있어서,According to paragraph 1,
    상기 화학식 1로 표시되는 화합물은 하기 화학식 9 내지 15 중 어느 하나로 표시되는 것인, 화합물:The compound represented by Formula 1 is represented by any one of the following Formulas 9 to 15:
    [화학식 9][Formula 9]
    Figure PCTKR2023021584-appb-img-000060
    Figure PCTKR2023021584-appb-img-000060
    [화학식 10][Formula 10]
    Figure PCTKR2023021584-appb-img-000061
    Figure PCTKR2023021584-appb-img-000061
    [화학식 11][Formula 11]
    Figure PCTKR2023021584-appb-img-000062
    Figure PCTKR2023021584-appb-img-000062
    [화학식 12][Formula 12]
    Figure PCTKR2023021584-appb-img-000063
    Figure PCTKR2023021584-appb-img-000063
    [화학식 13][Formula 13]
    Figure PCTKR2023021584-appb-img-000064
    Figure PCTKR2023021584-appb-img-000064
    [화학식 14][Formula 14]
    Figure PCTKR2023021584-appb-img-000065
    Figure PCTKR2023021584-appb-img-000065
    [화학식 15][Formula 15]
    Figure PCTKR2023021584-appb-img-000066
    Figure PCTKR2023021584-appb-img-000066
    (상기 화학식 9 내지 15에서,(In Formulas 9 to 15,
    X1, A1 내지 A5, a, b, c, f, g, L1 내지 L3, L6, Ar1, Ar2, 및 R1 내지 R5는 각각 제1항에 정의된 바와 같고,X 1 , A 1 to A 5 , A, B, C, F, L 1 to L 3 , L 6 , AR 1 , AR 2 , and R 1 to R 5 are shown in paragraph 1, respectively. ,
    n1 및 n2는 각각 0 내지 3의 정수이고,n1 and n2 are each integers from 0 to 3,
    o 및 p는 각각 0 내지 4의 정수이며,o and p are each integers from 0 to 4,
    복수의 R6 및 복수의 R7은 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, C6~C60의 아릴아민기, 핵원자수 5 내지 60의 헤테로아릴아민기, 및 (C6~C60의 아릴)(핵원자수 5 내지 60의 헤테로아릴)아민기로 이루어진 군에서 선택된 것임).A plurality of R 6 and a plurality of R 7 are the same or different from each other, and each independently represents hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 to C 40 alkyl group, and C 2 to C 40 alkenyl group. , C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 arylphosphine oxide group, C 6 ~ C 60 arylamine group, hetero of 5 to 60 nuclear atoms Arylamine group, and (C 6 ~ C 60 aryl) (heteroaryl of 5 to 60 nuclear atoms) amine group).
  5. 제1항에 있어서,According to paragraph 1,
    상기 R5는 수소, 중수소(D), 할로겐기, 시아노기, 및 하기 화학식 B1 내지 B25로 표시되는 치환체로 이루어진 군에서 선택된 것인, 화합물:The compound wherein R 5 is selected from the group consisting of hydrogen, deuterium (D), halogen group, cyano group, and substituents represented by the following formulas B1 to B25:
    Figure PCTKR2023021584-appb-img-000067
    Figure PCTKR2023021584-appb-img-000067
    Figure PCTKR2023021584-appb-img-000068
    Figure PCTKR2023021584-appb-img-000068
    (상기 화학식 B1 내지 B25에서, (In the above formulas B1 to B25,
    상기 화학식 B1 내지 B25에서, In the above formulas B1 to B25,
    a1은 0 내지 5의 정수이고,a1 is an integer from 0 to 5,
    a2는 0 내지 4의 정수이며,a2 is an integer from 0 to 4,
    a3는 0 내지 3의 정수이고,a3 is an integer from 0 to 3,
    a4는 0 내지 7의 정수이며,a4 is an integer from 0 to 7,
    a5는 0 내지 9의 정수이고,a5 is an integer from 0 to 9,
    a6는 0 내지 2의 정수이며,a6 is an integer from 0 to 2,
    W1 및 W2는 서로 동일하거나 상이하고, 각각 독립적으로 S, O, Si(R10)(R11), 및 C(R12)(R13)로 이루어진 군에서 선택되고,W 1 and W 2 are the same as or different from each other, and are each independently selected from the group consisting of S, O, Si(R 10 )(R 11 ), and C(R 12 )(R 13 ),
    W3는 S, O, Si(R14)(R15), C(R16)(R17) 및 N(R18)로 이루어진 군에서 선택되고,W 3 is selected from the group consisting of S, O, Si(R 14 )(R 15 ), C(R 16 )(R 17 ) and N(R 18 ),
    W4는 Si, Ge 또는 C이며,W 4 is Si, Ge or C,
    W5는 S 또는 O이고,W 5 is S or O,
    환 Cy1은 C6~C18의 축합 방향족환 또는 핵원자수 5~21개의 축합 헤테로방향족환이고,Ring Cy1 is a fused aromatic ring of C 6 to C 18 or a fused heteroaromatic ring of 5 to 21 nuclear atoms,
    복수의 R8은 서로 동일하거나 상이하고,A plurality of R 8 is the same or different from each other,
    R8 내지 R18은 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소(D), 할로겐기, 시아노기, 니트로기, 아미노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 또는 인접하는 기와 축합하여 축합 고리를 형성하고,R 8 to R 18 are the same or different from each other, and are each independently hydrogen, deuterium (D), halogen group, cyano group, nitro group, amino group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 arylphosphine oxide group, and C 6 ~ C 60 arylamine group selected from the group consisting of, or an adjacent group Condensates to form a condensed ring,
    상기 R8 내지 R18의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는, 각각 독립적으로 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이함).The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, aryl group of R 8 to R 18 The boron group, arylphosphine group, arylphosphine oxide group, and arylamine group each independently contain deuterium (D), halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C Substituted with one or more substituents selected from the group consisting of an aryl boron group of 6 to C 60 , an arylphosphine group of C 6 to C 60 , an arylphosphine oxide group of C 6 to C 60 , and an arylamine group of C 6 to C 60 or unsubstituted, wherein when the substituents are plural, they are the same or different from each other).
  6. 제1항에 있어서,According to paragraph 1,
    상기 화학식 1로 표시되는 화합물은 하기 화합물 1 내지 150으로 이루어진 군에서 선택된 것인, 화합물:The compound represented by Formula 1 is selected from the group consisting of the following compounds 1 to 150:
    Figure PCTKR2023021584-appb-img-000069
    Figure PCTKR2023021584-appb-img-000069
    Figure PCTKR2023021584-appb-img-000070
    Figure PCTKR2023021584-appb-img-000070
    Figure PCTKR2023021584-appb-img-000071
    Figure PCTKR2023021584-appb-img-000071
    Figure PCTKR2023021584-appb-img-000072
    Figure PCTKR2023021584-appb-img-000072
    Figure PCTKR2023021584-appb-img-000073
    .
    Figure PCTKR2023021584-appb-img-000073
    .
  7. 애노드; 캐소드; 상기 애노드와 캐소드 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며,anode; cathode; It includes one or more organic layers interposed between the anode and the cathode,
    상기 1층 이상의 유기물층 중 적어도 하나는 제1항 내지 제6항 중 어느 한 항에 기재된 화합물을 포함하는 유기 전계 발광 소자.An organic electroluminescent device wherein at least one of the one or more organic layers includes the compound according to any one of claims 1 to 6.
  8. 제7항에 있어서,In clause 7,
    상기 화합물을 포함하는 유기물층은 전자수송층 또는 전자수송 보조층인, 유기 전계 발광 소자. An organic electroluminescent device wherein the organic material layer containing the compound is an electron transport layer or an electron transport auxiliary layer.
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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20110015836A (en) * 2009-08-10 2011-02-17 다우어드밴스드디스플레이머티리얼 유한회사 Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR20170022940A (en) * 2015-08-21 2017-03-02 주식회사 엘지화학 Compound and organic electronic device comprising the same
CN108715592A (en) * 2017-08-31 2018-10-30 北京绿人科技有限责任公司 Compound and its application containing triazine group and a kind of organic electroluminescence device
KR20190070300A (en) * 2017-12-12 2019-06-20 시노라 게엠베하 Organic molecules for use in optoelectronic devices
KR20220063558A (en) * 2020-11-10 2022-05-17 솔루스첨단소재 주식회사 Organic compound and organic electroluminescent device comprising the same

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20110015836A (en) * 2009-08-10 2011-02-17 다우어드밴스드디스플레이머티리얼 유한회사 Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR20170022940A (en) * 2015-08-21 2017-03-02 주식회사 엘지화학 Compound and organic electronic device comprising the same
CN108715592A (en) * 2017-08-31 2018-10-30 北京绿人科技有限责任公司 Compound and its application containing triazine group and a kind of organic electroluminescence device
KR20190070300A (en) * 2017-12-12 2019-06-20 시노라 게엠베하 Organic molecules for use in optoelectronic devices
KR20220063558A (en) * 2020-11-10 2022-05-17 솔루스첨단소재 주식회사 Organic compound and organic electroluminescent device comprising the same

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