KR102679685B1 - Novel compound and organic light emitting device comprising the same - Google Patents
Novel compound and organic light emitting device comprising the same Download PDFInfo
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- KR102679685B1 KR102679685B1 KR1020190025298A KR20190025298A KR102679685B1 KR 102679685 B1 KR102679685 B1 KR 102679685B1 KR 1020190025298 A KR1020190025298 A KR 1020190025298A KR 20190025298 A KR20190025298 A KR 20190025298A KR 102679685 B1 KR102679685 B1 KR 102679685B1
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- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
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- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
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- C07C15/28—Anthracenes
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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Abstract
본 발명은 신규한 화합물 및 이를 이용한 유기발광 소자를 제공한다. The present invention provides a novel compound and an organic light-emitting device using the same.
Description
본 발명은 신규한 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다. The present invention relates to novel compounds and organic light-emitting devices containing them.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 넓은 시야각, 우수한 콘트라스트, 빠른 응답 시간을 가지며, 휘도, 구동 전압 및 응답 속도 특성이 우수하여 많은 연구가 진행되고 있다. In general, organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic light-emitting devices using the organic light-emitting phenomenon have a wide viewing angle, excellent contrast, fast response time, and excellent luminance, driving voltage, and response speed characteristics, so much research is being conducted.
유기 발광 소자는 일반적으로 양극과 음극 및 상기 양극과 음극 사이에 유기물 층을 포함하는 구조를 가진다. 상기 유기물 층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. Organic light emitting devices generally have a structure including an anode, a cathode, and an organic layer between the anode and the cathode. The organic material layer is often composed of a multi-layer structure made of different materials to increase the efficiency and stability of the organic light-emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of this organic light-emitting device, when a voltage is applied between two electrodes, holes are injected from the anode and electrons from the cathode into the organic material layer. When the injected holes and electrons meet, an exciton is formed, and this exciton When it falls back to the ground state, it glows.
상기와 같은 유기 발광 소자에 사용되는 유기물에 대하여 새로운 재료의 개발이 지속적으로 요구되고 있다.The development of new materials for organic materials used in organic light-emitting devices as described above is continuously required.
한편, 최근에는 공정 비용 절감을 위하여 기존의 증착 공정 대신 용액 공정, 특히 잉크젯 공정을 이용한 유기 발광 소자가 개발되고 있다. 초창기에는 모든 유기 발광 소자 층을 용액 공정으로 코팅하여 유기 발광 소자를 개발하려 하였으나 현재 기술로는 한계가 있어, 정구조 형태에서 HIL, HTL, EML만을 용액 공정으로 진행하고 추후 공정은 기존의 증착 공정을 활용하는 하이브리드(hybrid) 공정이 연구 중이다. Meanwhile, recently, in order to reduce process costs, organic light-emitting devices have been developed using a solution process, especially an inkjet process, instead of the existing deposition process. In the early days, attempts were made to develop organic light emitting devices by coating all organic light emitting device layers using a solution process, but there are limitations to the current technology, so only HIL, HTL, and EML in the form of a fixed structure were performed using a solution process, and the subsequent processes were carried out using the existing deposition process. A hybrid process utilizing is being studied.
이에 본 발명에서는 유기 발광 소자에 사용될 수 있으면서 동시에 용액 공정으로 증착이 가능한 신규한 유기 발광 소자의 소재를 제공한다. Accordingly, the present invention provides a novel organic light-emitting device material that can be used in organic light-emitting devices and can be deposited through a solution process.
본 발명은 신규한 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다. The present invention relates to novel heterocyclic compounds and organic light-emitting devices containing the same.
본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다.The present invention provides a compound represented by the following formula (1).
[화학식 1][Formula 1]
상기 화학식 1에서, In Formula 1,
Ar1 및 Ar2는 각각 독립적으로 치환 또는 비치환된 C6-60 아릴렌이고,Ar 1 and Ar 2 are each independently substituted or unsubstituted C 6-60 arylene,
Ar3 및 Ar4는 각각 독립적으로 치환 또는 비치환된 C6-60 아릴이고,Ar 3 and Ar 4 are each independently substituted or unsubstituted C 6-60 aryl,
n은 각각 독립적으로 0 내지 4의 정수이며,n is each independently an integer from 0 to 4,
Q는 각각 독립적으로 수소; 또는 치환 또는 비치환된 C1-60 알킬; 치환 또는 비치환된 C6-60 아릴; 치환 또는 비치환된 C1-30 알킬실릴; 또는 치환 또는 비치환된 C5-30 아릴실릴이고,Q is each independently hydrogen; or substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 6-60 aryl; Substituted or unsubstituted C 1-30 alkylsilyl; Or substituted or unsubstituted C 5-30 arylsilyl,
L은 하기 화학식 2 또는 3으로 표시되는 치환기이며,L is a substituent represented by the following formula 2 or 3,
[화학식 2][Formula 2]
[화학식 3][Formula 3]
상기 화학식 2 및 3에서,In Formulas 2 and 3,
R1 내지 R4는 각각 독립적으로 치환 또는 비치환된 C1-60 알킬; 치환 또는 비치환된 C1-60 할로알킬; 치환 또는 비치환된 C6-60 아릴; 치환 또는 비치환된 C1-30 알킬실릴; 또는 치환 또는 비치환된 C5-30 아릴실릴이고,R 1 to R 4 are each independently substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 1-60 haloalkyl; Substituted or unsubstituted C 6-60 aryl; Substituted or unsubstituted C 1-30 alkylsilyl; Or substituted or unsubstituted C 5-30 arylsilyl,
R5 내지 R12는 각각 독립적으로 수소; 치환 또는 비치환된 C1-60 알킬; 치환 또는 비치환된 C1-60 할로알킬; 치환 또는 비치환된 C6-60 아릴; 치환 또는 비치환된 C1-30 알킬실릴; 또는 치환 또는 비치환된 C5-30 아릴실릴이다.R 5 to R 12 are each independently hydrogen; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 1-60 haloalkyl; Substituted or unsubstituted C 6-60 aryl; Substituted or unsubstituted C 1-30 alkylsilyl; Or substituted or unsubstituted C 5-30 arylsilyl.
또한, 본 발명은 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물 층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화학식 1로 표시되는 화합물을 포함하는, 유기 발광 소자를 제공한다.In addition, the present invention includes a first electrode; a second electrode provided opposite to the first electrode; and an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by Formula 1. do.
상술한 화학식 1로 표시되는 화합물은 유기 발광 소자의 유기물 층의 재료로서 사용될 수 있으며, 유기 발광 소자에서 효율의 향상, 낮은 구동전압 및/또는 수명 특성을 향상시킬 수 있다. 특히, 상술한 화학식 1로 표시되는 화합물은 용액 공정에 적용할 수 있으며, 정공주입, 정공수송, 정공주입 및 수송, 발광, 전자수송, 또는 전자주입 재료로 사용될 수 있다.The compound represented by the above-described formula 1 can be used as a material for the organic layer of an organic light-emitting device, and can improve efficiency, low driving voltage, and/or lifespan characteristics of the organic light-emitting device. In particular, the compound represented by the above-mentioned formula 1 can be applied to a solution process and can be used as a hole injection, hole transport, hole injection and transport, light emitting, electron transport, or electron injection material.
도 1은 기판(1), 양극(2), 발광층(3), 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.
도 2는 기판 (1), 양극(2), 정공주입층(5), 정공수송층(6), 발광층(7), 전자수송층(8) 및 음극(4)로 이루어진 유기 발광 소자의 예를 도시한 것이다.Figure 1 shows an example of an organic light emitting device consisting of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
Figure 2 shows an example of an organic light emitting device consisting of a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (7), an electron transport layer (8), and a cathode (4). It was done.
이하, 본 발명의 이해를 돕기 위하여 보다 상세히 설명한다.Hereinafter, the present invention will be described in more detail to aid understanding.
본 발명은 상기 화학식 1로 표시되는 화합물을 제공한다. The present invention provides a compound represented by Formula 1 above.
본 명세서에서, 
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 아미노기; 포스핀옥사이드기; 알콕시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 알킬기; 사이클로알킬기; 알케닐기; 아릴기; 아르알킬기; 아르알케닐기; 알킬아릴기; 알킬아민기; 아랄킬아민기; 헤테로아릴아민기; 아릴아민기; 아릴포스핀기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 헤테로고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환되거나, 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환 또는 비치환된 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 비페닐기일 수 있다. 즉, 비페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 있다.As used herein, the term “substituted or unsubstituted” refers to deuterium; halogen group; Nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; Phosphine oxide group; Alkoxy group; Aryloxy group; Alkylthioxy group; Arylthioxy group; Alkyl sulphoxy group; Aryl sulfoxy group; silyl group; boron group; Alkyl group; Cycloalkyl group; alkenyl group; Aryl group; Aralkyl group; Aralkenyl group; Alkylaryl group; Alkylamine group; Aralkylamine group; heteroarylamine group; Arylamine group; Arylphosphine group; or substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups containing one or more of N, O and S atoms, or substituted or unsubstituted with two or more of the above-exemplified substituents linked. . For example, “a substituent group in which two or more substituents are connected” may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are connected.
본 명세서에서 카보닐기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 40인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In this specification, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound with the following structure, but is not limited thereto.
본 명세서에 있어서, 에스테르기는 에스테르기의 산소가 탄소수 1 내지 25의 직쇄, 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 25의 아릴기로 치환될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the oxygen of the ester group may be substituted with a straight-chain, branched-chain, or ring-chain alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
본 명세서에 있어서, 이미드기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 25인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In this specification, the carbon number of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound with the following structure, but is not limited thereto.
본 명세서에 있어서, 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다. In the present specification, the silyl group specifically includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited to this.
본 명세서에 있어서, 붕소기는 구체적으로 트리메틸붕소기, 트리에틸붕소기, t-부틸디메틸붕소기, 트리페닐붕소기, 페닐붕소기 등이 있으나 이에 한정되지 않는다.In the present specification, the boron group specifically includes trimethyl boron group, triethyl boron group, t-butyldimethyl boron group, triphenyl boron group, and phenyl boron group, but is not limited thereto.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.In this specification, examples of halogen groups include fluorine, chlorine, bromine, or iodine.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 6이다. 알킬기의 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸, 1-메틸-부틸, 1-에틸-부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 헥실, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸-2-펜틸, 3,3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸, 1-메틸헥실, 사이클로펜틸메틸,사이클로헥틸메틸, 옥틸, n-옥틸, tert-옥틸, 1-메틸헵틸, 2-에틸헥실, 2-프로필펜틸, n-노닐, 2,2-디메틸헵틸, 1-에틸-프로필, 1,1-디메틸-프로필, 이소헥실, 2-메틸펜틸, 4-메틸헥실, 5-메틸헥실 등이 있으나, 이들에 한정되지 않는다.In the present specification, the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the carbon number of the alkyl group is 1 to 20. According to another embodiment, the carbon number of the alkyl group is 1 to 10. According to another embodiment, the carbon number of the alkyl group is 1 to 6. Specific examples of alkyl groups include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n. -pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but is not limited to these.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 6이다. 구체적인 예로는 비닐, 1-프로페닐, 이소프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 1-펜테닐, 2-펜테닐, 3-펜테닐, 3-메틸-1-부테닐, 1,3-부타디에닐, 알릴, 1-페닐비닐-1-일, 2-페닐비닐-1-일, 2,2-디페닐비닐-1-일, 2-페닐-2-(나프틸-1-일)비닐-1-일, 2,2-비스(디페닐-1-일)비닐-1-일, 스틸베닐기, 스티레닐기 등이 있으나 이들에 한정되지 않는다.In the present specification, the alkenyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group, etc., but are not limited to these.
본 명세서에 있어서, 사이클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 일 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 사이클로프로필, 사이클로부틸, 사이클로펜틸, 3-메틸사이클로펜틸, 2,3-디메틸사이클로펜틸, 사이클로헥실, 3-메틸사이클로헥실, 4-메틸사이클로헥실, 2,3-디메틸사이클로헥실, 3,4,5-트리메틸사이클로헥실, 4-tert-부틸사이클로헥실, 사이클로헵틸, 사이클로옥틸 등이 있으나, 이에 한정되지 않는다.In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, Examples include, but are not limited to, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며, 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트릴기, 파이레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, such as a phenyl group, biphenyl group, or terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.
본 명세서에 있어서, 플루오레닐기는 치환될 수 있고, 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다. 상기 플루오레닐기가 치환되는 경우, 
본 명세서에 있어서, 헤테로고리기는 이종 원소로 O, N, Si 및 S 중 1개 이상을 포함하는 헤테로고리기로서, 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 60인 것이 바람직하다. 헤테로고리기의 예로는 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기, 아크리딜기, 피리다진기, 피라지닐기, 퀴놀리닐기, 퀴나졸린기, 퀴녹살리닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤조옥사졸기, 벤조이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 페난쓰롤린기(phenanthroline), 이소옥사졸릴기, 티아디아졸릴기, 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si, and S as heterogeneous elements, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, and acridyl group. , pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , carbazole group, benzooxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, isoxazolyl group, thiadia These include, but are not limited to, a zolyl group, a phenothiazinyl group, and a dibenzofuranyl group.
본 명세서에 있어서, 아르알킬기, 아르알케닐기, 알킬아릴기, 아릴아민기 중의 아릴기는 전술한 아릴기의 예시와 같다. 본 명세서에 있어서, 아르알킬기, 알킬아릴기, 알킬아민기 중 알킬기는 전술한 알킬기의 예시와 같다. 본 명세서에 있어서, 헤테로아릴아민 중 헤테로아릴은 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 아르알케닐기 중 알케닐기는 전술한 알케닐기의 예시와 같다. 본 명세서에 있어서, 아릴렌은 2가기인 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 헤테로아릴렌은 2가기인 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 탄화수소 고리는 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 아릴기 또는 사이클로알킬기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 헤테로고리는 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다.In this specification, the aryl group among the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above. In this specification, the aralkyl group, alkylaryl group, and alkylamine group are the same as the examples of the alkyl group described above. In the present specification, the description regarding the heterocyclic group described above may be applied to heteroaryl among heteroarylamines. In this specification, the alkenyl group among the aralkenyl groups is the same as the example of the alkenyl group described above. In this specification, the description of the aryl group described above can be applied, except that arylene is a divalent group. In the present specification, the description of the heterocyclic group described above can be applied, except that heteroarylene is a divalent group. In the present specification, the description of the aryl group or cycloalkyl group described above may be applied, except that the hydrocarbon ring is not monovalent and is formed by combining two substituents. In the present specification, the description of the heterocyclic group described above can be applied, except that the heterocycle is not a monovalent group and is formed by combining two substituents.
바람직하게는, R1 내지 R4는 각각 독립적으로 C1-10 알킬일 수 있으며, 보다 바람직하게는, 메틸, 에틸, 프로필 또는 헥실일 수 있다.Preferably, R 1 to R 4 may each independently be C 1-10 alkyl, and more preferably methyl, ethyl, propyl or hexyl.
바람직하게는, R5 내지 R12는 각각 독립적으로 수소; 또는 C1-10 알킬일 수 있으며, 보다 바람직하게는, 수소, 메틸, 에틸, 프로필 또는 헥실일 수 있다.Preferably, R 5 to R 12 are each independently hydrogen; Or it may be C 1-10 alkyl, and more preferably hydrogen, methyl, ethyl, propyl or hexyl.
바람직하게는, Ar1 및 Ar2는 각각 독립적으로 치환 또는 비치환된 페닐렌, 치환 또는 비치환된 비페닐디일, 치환 또는 비치환된 나프탈렌디일, 치환 또는 비치환된 -(페닐렌)(나프틸렌디일)- 또는 치환 또는 비치환된 -(페닐렌)(나프틸렌디일)(페닐렌)- 일 수 있으며, 보다 구체적으로 Ar1 및 Ar2는 각각 독립적으로, 하기로 구성되는 군으로부터 선택되는 어느 하나일 수 있다.Preferably, Ar 1 and Ar 2 are each independently substituted or unsubstituted phenylene, substituted or unsubstituted biphenyldiyl, substituted or unsubstituted naphthalenediyl, substituted or unsubstituted -(phenylene)(naph) thylenediyl)- or substituted or unsubstituted -(phenylene)(naphthylenediyl)(phenylene)-, and more specifically, Ar 1 and Ar 2 are each independently selected from the group consisting of It could be any one.
상기 화학식에서 R20은 수소 또는 C1-10 알킬이다.In the above formula, R 20 is hydrogen or C 1-10 alkyl.
바람직하게는, Ar3 및 Ar4는 각각 독립적으로, 하기로 구성되는 군으로부터 선택되는 어느 하나일 수 있다.Preferably, Ar 3 and Ar 4 may each independently be selected from the group consisting of:
상기 화학식에서 R21은 수소 또는 C1-10 알킬이다.In the above formula, R 21 is hydrogen or C 1-10 alkyl.
바람직하게는, n은 각각 독립적으로 0 내지 2의 정수이며, Q는 각각 독립적으로 수소; 또는 C1-10 알킬일 수 있으며, 보다 바람직하게는, n은 0 또는 2이며, Q는 수소; 또는 t-부틸일 수 있다.Preferably, n is each independently an integer from 0 to 2, and Q is each independently hydrogen; Or it may be C 1-10 alkyl, more preferably, n is 0 or 2, and Q is hydrogen; Or it may be t-butyl.
바람직하게는, 상기 화학식 1로 표시되는 화합물은, 하기 화합물로 구성되는 군으로부터 선택될 수 있다.Preferably, the compound represented by Formula 1 may be selected from the group consisting of the following compounds.
상기 화학식 1로 표시되는 화합물은 하기 반응식 1 또는 2와 같은 제조 방법으로 제조할 수 있다. 상기 제조 방법은 후술할 제조예에서 보다 구체화될 수 있다.The compound represented by Formula 1 can be prepared by the production method shown in Scheme 1 or 2 below. The manufacturing method may be further detailed in the manufacturing examples described later.
[반응식 1][Scheme 1]
[반응식 2][Scheme 2]
상기 반응을 위한 반응기는 당업계에 알려진 바에 따라 변경이 가능하며, 상기 제조 방법은 후술할 제조예에서 보다 구체화될 수 있다. 또한, 상기 화학식 1로 표시되는 화합물은 상기 반응식 1 또는 2를 참고하여 제조하고자 하는 화합물의 구조에 맞추어 출발 물질을 적절히 대체하여 제조할 수 있다.The reactor for the reaction can be changed according to what is known in the art, and the manufacturing method can be more detailed in the manufacturing example to be described later. In addition, the compound represented by Formula 1 can be prepared by appropriately replacing the starting materials according to the structure of the compound to be prepared by referring to Scheme 1 or 2.
또한, 본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기 발광 소자를 제공한다. 일례로, 본 발명은 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물 층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화학식 1로 표시되는 화합물을 포함하는, 유기 발광 소자를 제공한다. Additionally, the present invention provides an organic light-emitting device containing the compound represented by Formula 1 above. In one example, the present invention includes a first electrode; a second electrode provided opposite to the first electrode; and an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by Formula 1. do.
본 발명의 유기 발광 소자의 유기물 층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 발명의 유기 발광 소자는 유기물 층으로서 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등을 포함하는 구조를 가질 수 있다. 그러나 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기층을 포함할 수 있다.The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure that includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer. However, the structure of the organic light emitting device is not limited to this and may include fewer organic layers.
또한, 상기 유기물 층은 정공주입층, 정공수송층, 또는 정공 주입과 수송을 동시에 하는 층을 포함할 수 있고, 상기 정공주입층, 정공수송층, 또는 정공 주입과 수송을 동시에 하는 층은 상기 화학식 1로 표시되는 화합물을 포함한다. In addition, the organic material layer may include a hole injection layer, a hole transport layer, or a layer that simultaneously performs hole injection and transport, and the hole injection layer, the hole transport layer, or a layer that simultaneously performs hole injection and transport is represented by Formula 1 Contains the indicated compounds.
또한, 상기 유기물 층은 발광층을 포함할 수 있고, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 포함한다. Additionally, the organic layer may include a light-emitting layer, and the light-emitting layer includes the compound represented by Chemical Formula 1.
또한, 상기 유기물 층은 정공수송층, 또는 정공주입층을 포함할 수 있고, 상기 정공수송층, 또는 정공주입층은 상기 화학식 1로 표시되는 화합물을 포함한다.Additionally, the organic material layer may include a hole transport layer or a hole injection layer, and the hole transport layer or the hole injection layer includes the compound represented by Formula 1 above.
또한, 상기 전자수송층, 전자주입층, 또는 전자수송 및 전자주입을 동시에 하는 층은 상기 화학식 1로 표시되는 화합물을 포함한다. In addition, the electron transport layer, the electron injection layer, or the layer that simultaneously performs electron transport and electron injection includes the compound represented by Formula 1.
또한, 상기 유기물 층은 발광층 및 정공수송층을 포함하고, 상기 정공수송층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. Additionally, the organic layer includes a light-emitting layer and a hole transport layer, and the hole transport layer may include the compound represented by Formula 1.
또한, 본 발명에 따른 유기 발광 소자는, 기판 상에 양극, 1층 이상의 유기물 층 및 음극이 순차적으로 적층된 구조(normal type)의 유기 발광 소자일 수 있다. 또한, 본 발명에 따른 유기 발광 소자는 기판 상에 음극, 1층 이상의 유기물 층 및 양극이 순차적으로 적층된 역방향 구조(inverted type)의 유기 발광 소자일 수 있다. 예컨대, 본 발명의 일실시예에 따른 유기 발광 소자의 구조는 도 1 및 2에 예시되어 있다.Additionally, the organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. Additionally, the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.
도 1은 기판(1), 양극(2), 발광층(3), 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 발광층에 포함될 수 있다. Figure 1 shows an example of an organic light emitting device consisting of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. In this structure, the compound represented by Formula 1 may be included in the light-emitting layer.
도 2는 기판 (1), 양극(2), 정공주입층(5), 정공수송층(6), 발광층(7), 전자수송층(8) 및 음극(4)로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 정공주입층, 정공수송층, 발광층 및 전자수송층 중 1층 이상에 포함될 수 있다. Figure 2 shows an example of an organic light emitting device consisting of a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (7), an electron transport layer (8), and a cathode (4). It was done. In this structure, the compound represented by Formula 1 may be included in one or more of the hole injection layer, hole transport layer, light emitting layer, and electron transport layer.
본 발명에 따른 유기 발광 소자는, 상기 유기물 층 중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다. 또한, 상기 유기 발광 소자가 복수개의 유기물층을 포함하는 경우, 상기 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다. The organic light emitting device according to the present invention can be manufactured using materials and methods known in the art, except that at least one of the organic layers includes the compound represented by Formula 1 above. Additionally, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
예컨대, 본 발명에 따른 유기 발광 소자는 기판 상에 제1 전극, 유기물층 및 제2 전극을 순차적으로 적층시켜 제조할 수 있다. 이때, 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 PVD(physical Vapor Deposition)방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공 주입층, 정공 수송층, 발광층 및 전자 수송층을 포함하는 유기물 층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시켜 제조할 수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수 있다. For example, the organic light emitting device according to the present invention can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation is used to deposit a metal or a conductive metal oxide or an alloy thereof on the substrate to form an anode. It can be manufactured by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device can be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
또한, 상기 화학식 1로 표시되는 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물 층으로 형성될 수 있다. 특히, 상기 화학식 1로 표시되는 화합물은 용액 도포법에 사용되는 용매에 대한 용해도가 우수하여, 용액 도포법을 적용하기 용이하다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.Additionally, the compound represented by Formula 1 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. In particular, the compound represented by Formula 1 has excellent solubility in the solvent used in the solution application method, making it easy to apply the solution application method. Here, the solution application method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.
이에, 본 발명은 상기 화학식 1로 표시되는 화합물 및 용매를 포함하는 코팅 조성물을 제공한다. Accordingly, the present invention provides a coating composition comprising the compound represented by Formula 1 and a solvent.
상기 용매는 본 발명에 따른 화합물을 용해 또는 분산시킬 수 있는 용매이면 특별히 제한되지 않으며, 일례로 클로로포름, 염화메틸렌, 1,2-디클로로에탄, 1,1,2-트리클로로에탄, 클로로벤젠, o-디클로로벤젠 등의 염소계 용매; 테트라하이드로퓨란, 디옥산 등의 에테르계 용매; 톨루엔, 크실렌, 트리메틸벤젠, 메시틸렌 등의 방향족 탄화수소계 용매; 시클로헥산, 메틸시클로헥산, n-펜탄, n-헥산, n-헵탄, n-옥탄, n-노난, n-데칸 등의 지방족 탄화수소계 용매; 아세톤, 메틸에틸케톤, 시클로헥사논 등의 케톤계 용매; 아세트산에틸, 아세트산부틸, 에틸셀로솔브아세테이트 등의 에스테르계 용매; 에틸렌글리콜, 에틸렌글리콜모노부틸에테르, 에틸렌글리콜모노에틸에테르, 에틸렌글리콜모노메틸에테르, 디메톡시에탄, 프로필렌글리콜, 디에톡시메탄, 트리에틸렌글리콜모노에틸에테르, 글리세린, 1,2-헥산디올 등의 다가 알코올 및 그의 유도체; 메탄올, 에탄올, 프로판올, 이소프로판올, 시클로헥산올 등의 알코올계 용매; 디메틸술폭사이드 등의 술폭사이드계 용매; 및 N-메틸-2-피롤리돈, N,N-디메틸포름아미드 등의 아미드계 용매; 부틸벤조에이트, 메틸-2-메톡시벤조에이트 등의 벤조에이트계 용매; 테트랄린; 3-phenoxy-toluene 등의 용매를 들 수 있다. 또한, 상술한 용매를 1종 단독으로 사용하거나 2종 이상의 용매를 혼합하여 사용할 수 있다. The solvent is not particularly limited as long as it is capable of dissolving or dispersing the compound according to the present invention, and examples include chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o -Chlorine-based solvents such as dichlorobenzene; Ether-based solvents such as tetrahydrofuran and dioxane; Aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, and mesitylene; Aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; Ketone-based solvents such as acetone, methyl ethyl ketone, and cyclohexanone; Ester solvents such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; Polyhydric acids such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol, etc. alcohol and its derivatives; Alcohol-based solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; Sulfoxide-based solvents such as dimethyl sulfoxide; and amide-based solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; Benzoate-based solvents such as butyl benzoate and methyl-2-methoxybenzoate; tetralin; Solvents such as 3-phenoxy-toluene may be mentioned. In addition, the above-mentioned solvents can be used alone or in a mixture of two or more solvents.
또한, 상기 코팅 조성물의 점도는 1 cP 내지 10 cP가 바람직하며, 상기의 범위에서 코팅이 용이하다. 또한, 상기 코팅 조성물 내 본 발명에 따른 화합물의 농도는 0.1 wt/v% 내지 20 wt/v%인 것이 바람직하다. Additionally, the viscosity of the coating composition is preferably 1 cP to 10 cP, and coating is easy within this range. In addition, the concentration of the compound according to the present invention in the coating composition is preferably 0.1 wt/v% to 20 wt/v%.
또한, 본 발명은 상술한 코팅 조성물을 사용하여 기능층을 형성하는 방법을 제공한다. 구체적으로, 상술한 본 발명에 따른 코팅 조성물을 용액 공정으로 코팅하는 단계; 및 상기 코팅된 코팅 조성물을 열처리하는 단계를 포함한다. Additionally, the present invention provides a method of forming a functional layer using the above-described coating composition. Specifically, coating the coating composition according to the present invention described above by a solution process; and heat treating the coated coating composition.
상기 열처리 단계에서 열처리 온도는 150 내지 230℃가 바람직하다. 또한, 상기 열처리 시간은 1분 내지 3시간이고, 보다 바람직하게는 10분 내지 1시간이다. 또한, 상기 열처리는 아르곤, 질소 등의 불활성 기체 분위기에서 수행하는 것이 바람직하다. In the heat treatment step, the heat treatment temperature is preferably 150 to 230°C. Additionally, the heat treatment time is 1 minute to 3 hours, and more preferably 10 minutes to 1 hour. Additionally, the heat treatment is preferably performed in an inert gas atmosphere such as argon or nitrogen.
일례로, 상기 제1 전극은 양극이고, 상기 제2 전극은 음극이거나, 또는 상기 제1 전극은 음극이고, 상기 제2 전극은 양극이다.In one example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.
상기 양극 물질로는 통상 유기물 층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 상기 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO), 인듐아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SNO2:Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다. The anode material is generally preferably a material with a large work function to facilitate hole injection into the organic layer. Specific examples of the anode material 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 poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline are included, but are not limited to these.
상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 상기 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다. The cathode material is generally preferably a material with a small work function to facilitate electron injection into the organic layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are, but are not limited to, multi-layered materials such as LiF/Al or LiO 2 /Al.
상기 정공 주입 물질로는 전극으로부터 정공을 주입하는 층으로, 정공 주입 물질로는 정공을 수송하는 능력을 가져 양극에서의 정공 주입효과, 발광층 또는 발광재료에 대하여 우수한 정공 주입 효과를 갖고, 발광층에서 생성된 여기자의 전자주입층 또는 전자주입재료에의 이동을 방지하며, 또한, 박막 형성 능력이 우수한 화합물이 바람직하다. 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물 층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린(porphyrin), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴헥사아자트리페닐렌 계열의 유기물, 퀴나크리돈(quinacridone)계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정 되는 것은 아니다. The hole injection material is a layer that injects holes from the electrode. The hole injection material has the ability to transport holes and has an excellent hole injection effect at the anode, a light-emitting layer or a light-emitting material, and is generated in the light-emitting layer. A compound that prevents movement of excitons to the electron injection layer or electron injection material and has excellent thin film forming ability is preferred. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrilehexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic materials, anthraquinone, polyaniline, and polythiophene series conductive polymers, etc., but are not limited to these.
상기 정공수송층은 정공주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로, 정공 수송 물질로 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다. The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light-emitting layer. It is a hole transport material that can receive holes from the anode or hole injection layer and transfer them to the light-emitting layer, and is a material with high mobility for holes. This is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions, but are not limited to these.
상기 발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 구체적인 예로 8-히드록시-퀴놀린 알루미늄 착물(Alq3); 카르바졸 계열 화합물; 이량체화 스티릴(dimerized styryl) 화합물; BAlq; 10-히드록시벤조 퀴놀린-금속 화합물; 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물; 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자; 스피로(spiro) 화합물; 폴리플루오렌, 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다. The light-emitting material is a material capable of emitting light in the visible range by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV) series polymer; Spiro compounds; Polyfluorene, rubrene, etc., but are not limited to these.
상기 발광층은 호스트 재료 및 도펀트 재료를 포함할 수 있다. 호스트 재료는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. 구체적으로 축합 방향족환 유도체로는 안트라센 유도체, 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고, 헤테로환 함유 화합물로는 카바졸 유도체, 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이에 한정되지 않는다. 바람직하게는, 상기 호스트 재료로서 본 발명에 따른 화합물을 사용한다. 또한, 상기 발광층은 2종 이상의 호스트가 사용될 수 있고, 상기 호스트 중 하나로 본 발명에 따른 화합물을 사용할 수 있다.The light emitting layer may include a host material and a dopant material. Host materials include condensed aromatic ring derivatives or heterocyclic ring-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type compounds. These include, but are not limited to, furan compounds and pyrimidine derivatives. Preferably, a compound according to the present invention is used as the host material. Additionally, the light-emitting layer may use two or more types of hosts, and the compound according to the present invention may be used as one of the hosts.
도펀트 재료로는 방향족 아민 유도체, 스트릴아민 화합물, 붕소 착체, 플루오란텐 화합물, 금속 착체 등이 있다. 구체적으로 방향족 아민 유도체로는 치환 또는 비치환된 아릴아미노기를 갖는 축합 방향족환 유도체로서, 아릴아미노기를 갖는 피렌, 안트라센, 크리센, 페리플란텐 등이 있으며, 스티릴아민 화합물로는 치환 또는 비치환된 아릴아민에 적어도 1개의 아릴비닐기가 치환되어 있는 화합물로, 아릴기, 실릴기, 알킬기, 사이클로알킬기 및 아릴아미노기로 이루어진 군에서 1 또는 2 이상 선택되는 치환기가 치환 또는 비치환된다. 구체적으로 스티릴아민, 스티릴디아민, 스티릴트리아민, 스티릴테트라아민 등이 있으나, 이에 한정되지 않는다. 또한, 금속 착체로는 이리듐 착체, 백금 착체 등이 있으나, 이에 한정되지 않는다.Dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, and periplanthene, and styrylamine compounds include substituted or unsubstituted arylamino groups. It is a compound in which at least one arylvinyl group is substituted on the arylamine, and is substituted or unsubstituted with one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group, and arylamino group. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc. are included, but are not limited thereto. Additionally, metal complexes include, but are not limited to, iridium complexes and platinum complexes.
상기 전자 수송 물질로는 전자주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 층으로 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 Al 착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다. 전자 수송층은 종래기술에 따라 사용된 바와 같이 임의의 원하는 캐소드 물질과 함께 사용할 수 있다. 특히, 적절한 캐소드 물질의 예는 낮은 일함수를 가지고 알루미늄층 또는 실버층이 뒤따르는 통상적인 물질이다. 구체적으로 세슘, 바륨, 칼슘, 이테르븀 및 사마륨이고, 각 경우 알루미늄 층 또는 실버층이 뒤따른다.The electron transport material is a layer that receives electrons from the electron injection layer and transports electrons to the light-emitting layer. The electron transport material is a material that can easily inject electrons from the cathode and transfer them to the light-emitting layer, and has high mobility for electrons. This is suitable. Specific examples include Al complex of 8-hydroxyquinoline; Complex containing Alq 3 ; organic radical compounds; Hydroxyflavone-metal complexes, etc., but are not limited to these. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials with a low work function followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.
상기 전자주입층은 전극으로부터 전자를 주입하는 층으로, 전자를 수송하는 능력을 갖고, 음극으로부터의 전자 주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며, 발광층에서 생성된 여기자의 정공주입층에의 이동을 방지하고, 또한, 박막형성능력이 우수한 화합물이 바람직하다. 구체적으로는 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 질소 함유 5원환 유도체 등이 있으나, 이에 한정되지 않는다. The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect to the light-emitting layer or light-emitting material, and hole injection of excitons generated in the light-emitting layer. A compound that prevents movement to the layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, metals. These include, but are not limited to, complex compounds and nitrogen-containing five-membered ring derivatives.
상기 금속 착체 화합물로서는 8-하이드록시퀴놀리나토 리튬, 비스(8-하이드록시퀴놀리나토)아연, 비스(8-하이드록시퀴놀리나토)구리, 비스(8-하이드록시퀴놀리나토)망간, 트리스(8-하이드록시퀴놀리나토)알루미늄, 트리스(2-메틸-8-하이드록시퀴놀리나토)알루미늄, 트리스(8-하이드록시퀴놀리나토)갈륨, 비스(10-하이드록시벤조[h]퀴놀리나토)베릴륨, 비스(10-하이드록시벤조[h]퀴놀리나토)아연, 비스(2-메틸-8-퀴놀리나토)클로로갈륨, 비스(2-메틸-8-퀴놀리나토)(o-크레졸라토)갈륨, 비스(2-메틸-8-퀴놀리나토)(1-나프톨라토)알루미늄, 비스(2-메틸-8-퀴놀리나토)(2-나프톨라토)갈륨 등이 있으나, 이에 한정되지 않는다.Examples of the metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, Tris(2-methyl-8-hydroxyquinolinato)aluminum, Tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato) aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato) gallium, etc. It is not limited to this.
본 발명에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light emitting device according to the present invention may be a front emitting type, a back emitting type, or a double-sided emitting type depending on the material used.
또한, 상기 화학식 1로 표시되는 화합물은 유기 발광 소자 외에도 유기 태양 전지 또는 유기 트랜지스터에 포함될 수 있다.Additionally, the compound represented by Formula 1 may be included in organic solar cells or organic transistors in addition to organic light-emitting devices.
상기 화학식 1로 표시되는 화합물 및 이를 포함하는 유기 발광 소자의 제조는 이하 실시예에서 구체적으로 설명한다. 그러나 하기 실시예는 본 발명을 예시하기 위한 것이며, 본 발명의 범위가 이들에 의하여 한정되는 것은 아니다.The preparation of the compound represented by Formula 1 and an organic light-emitting device containing the same will be described in detail in the following Examples. However, the following examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.
<제조예><Manufacturing example>
<제조예 1> - 화합물 1의 제조<Preparation Example 1> - Preparation of Compound 1
1) 중간체 1-1의 합성1) Synthesis of intermediate 1-1
1,4-dibromo-2,5-dimethylbenzene (5.28 g, 20 mmol)과 THF (60 mL)를 RBF에 담은 뒤 질소 치환하고 -78 oC로 냉각한다. n-BuLi (8.8 mL, 2.5 M Hex)을 천천히 넣어준 뒤, -78 oC에서 30분간 교반한다. CuCN (896 mg, 10 mmol)을 넣어준 뒤 0 oC에서 30분간 교반한다. Duroquinone (4.93 g, 30 mmol)을 THF (40 mL)에 녹인 용액을 RT에서 천천히 투입한다. 상온에서 밤새 교반한다. THF/brine으로 work-up 후 유기층은 MgSO4로 물을 제거한 뒤 여과하였다. 여과액은 진공 건조한 뒤 MPLC 정제하여 중간체 1-1 (3.1 g)을 수득하였다.1,4-dibromo-2,5-dimethylbenzene (5.28 g, 20 mmol) and THF (60 mL) were placed in RBF, purged with nitrogen, and cooled to -78 o C. Slowly add n -BuLi (8.8 mL, 2.5 M Hex) and stir at -78 o C for 30 minutes. CuCN (896 mg, 10 mmol) was added and stirred at 0 o C for 30 minutes. A solution of duroquinone (4.93 g, 30 mmol) dissolved in THF (40 mL) is slowly added at RT. Stir overnight at room temperature. After work-up with THF/brine, the organic layer was filtered after removing water with MgSO 4 . The filtrate was vacuum dried and purified by MPLC to obtain Intermediate 1-1 (3.1 g).
2) 중간체 1-2의 합성2) Synthesis of intermediate 1-2
B2pin2 (6.8 g, 26.7 mmol), PdCl2dppfCH2Cl2 (910 mg, 1.11 mmol), KOAc (3.28 g, 33.3 mmol)을 RBF에 넣고 질소 치환한다. 중간체 1-1 (4.1 g, 11.1 mmol)을 Dioxane (22 mL)에 녹인 용액을 투입 후 90 oC에서 밤새 교반한다. EA/brine으로 work-up 후 유기층은 MgSO4로 물을 제거한 뒤 여과하였다. 여과액은 진공 건조한 뒤 MPLC 정제하여 중간체 1-2 (3.15 g)을 수득하였다.B 2 pin 2 (6.8 g, 26.7 mmol), PdCl 2 dppfCH 2 Cl 2 (910 mg, 1.11 mmol), and KOAc (3.28 g, 33.3 mmol) were added to RBF and purged with nitrogen. Add a solution of Intermediate 1-1 (4.1 g, 11.1 mmol) in dioxane (22 mL) and stir at 90 o C overnight. After work-up with EA/brine, the organic layer was filtered after removing water with MgSO 4 . The filtrate was dried under vacuum and purified by MPLC to obtain Intermediate 1-2 (3.15 g).
3) 화합물 1의 합성3) Synthesis of Compound 1
중간체 1-2 (3.31 g, 7.2 mmol), SM-Br (1.39 g, 3 mmol), Pd(PPh3)4 (347 mg, 0.3 mmol), Cs2CO3 (4.89 g, 15 mmol)을 RBF에 넣고 질소로 치환한다. THF (12 mL)와 H2O (3 mL)를 투입 후 90 oC에서 48시간 동안 교반한다. THF/brine으로 work-up 후 유기층은 MgSO4로 물을 제거한 뒤 여과하였다. 여과액은 진공 건조한 뒤 MPLC 정제하고 Toluene/Hex 조건에서 침전 정제하여 화합물 1 (540 mg)을 확보하였다.Intermediate 1-2 (3.31 g, 7.2 mmol), SM-Br (1.39 g, 3 mmol), Pd(PPh 3 ) 4 (347 mg, 0.3 mmol), Cs 2 CO 3 (4.89 g, 15 mmol) was reacted with RBF. and replace with nitrogen. Add THF (12 mL) and H 2 O (3 mL) and stir at 90 o C for 48 hours. After work-up with THF/brine, the organic layer was filtered after removing water with MgSO 4 . The filtrate was dried under vacuum, purified by MPLC, and purified by precipitation under Toluene/Hex conditions to obtain Compound 1 (540 mg).
화합물 1의 NMR 측정 값: 1H NMR (500 MHz, CD2Cl2) δ 8.12 (d, 2H), 8.06 (d, 2H), 7.89 (s, 4H), 7.77 - 7.71 (m, 6H), 7.68 - 7.66 (m, 2H), 7.63 - 7.60 (m, 4H), 7.54 - 7.51 (m, 2H), 7.46 - 7.43 (m, 6H), 7.41 - 7.38 (m, 4H), 7.29 - 7.24 (m, 6H), 7.22 (s, 2H), 7.15 (d, 2H), 2.53 (s, 6H), 2.27 (s, 6H)NMR measurements of compound 1: 1 H NMR (500 MHz, CD 2 Cl 2 ) δ 8.12 (d, 2H), 8.06 (d, 2H), 7.89 (s, 4H), 7.77 - 7.71 (m, 6H), 7.68 - 7.66 (m, 2H), 7.63 - 7.60 (m, 4H), 7.54 - 7.51 (m, 2H), 7.46 - 7.43 (m, 6H), 7.41 - 7.38 (m, 4H), 7.29 - 7.24 (m) , 6H), 7.22 (s, 2H), 7.15 (d, 2H), 2.53 (s, 6H), 2.27 (s, 6H)
<제조예 2> - 화합물 2의 제조<Preparation Example 2> - Preparation of Compound 2
1) 중간체 2-1의 합성1) Synthesis of intermediate 2-1
1,4-dibromo-2,5-dimethylbenzene (10.6 g, 40 mmol), B2pin2 (24.4 g, 96 mmol), PdCl2dppfCH2Cl2 (3.27 g, 4 mmol), KOAc (19.7 g, 200 mmol)을 RBF에 넣고 질소 치환한다. Dioxane (80 mL)에 녹인 용액을 투입 후 100 oC에서 3시간 교반한다. DCM/brine으로 work-up 후 유기층은 MgSO4로 물을 제거한 뒤 여과하였다. 여과액은 진공 건조한 뒤 MPLC 정제하여 중간체 2-1 (10.8 g)을 수득하였다.1,4-dibromo-2,5-dimethylbenzene (10.6 g, 40 mmol), B 2 pin 2 (24.4 g, 96 mmol), PdCl 2 dppfCH 2 Cl 2 (3.27 g, 4 mmol), KOAc (19.7 g, 200 mmol) was added to RBF and purged with nitrogen. Add the solution dissolved in dioxane (80 mL) and stir at 100 o C for 3 hours. After work-up with DCM/brine, the organic layer was filtered after removing water with MgSO 4 . The filtrate was dried under vacuum and purified by MPLC to obtain Intermediate 2-1 (10.8 g).
2) 중간체 2-2의 합성2) Synthesis of intermediate 2-2
SM-boronic acid (12.7 g, 30 mmol), Pd(PPh3)4 (1.73 g, 1.5 mmol), K2CO3 (12.4 g, 90 mmol)을 RBF에 넣고 질소로 치환한다. 2-Bromo-5-iodotoluene (5.51 mL, 39 mmol), THF (120 mL)와 H2O (30 mL)를 투입 후 90 oC에서 8시간 동안 교반한다. DCM/brine으로 work-up 후 유기층은 MgSO4로 물을 제거한 뒤 여과하였다. 여과액은 진공 건조한 뒤 MPLC 정제하고 EA에서 re-slurry 정제하여 중간체 2-2 (5.8 g)을 확보하였다.SM-boronic acid (12.7 g, 30 mmol), Pd(PPh 3 ) 4 (1.73 g, 1.5 mmol), and K 2 CO 3 (12.4 g, 90 mmol) were added to RBF and replaced with nitrogen. Add 2-Bromo-5-iodotoluene (5.51 mL, 39 mmol), THF (120 mL) and H 2 O (30 mL) and stir at 90 o C for 8 hours. After work-up with DCM/brine, the organic layer was filtered after removing water with MgSO 4 . The filtrate was vacuum dried, purified by MPLC, and re-slurry purified by EA to obtain intermediate 2-2 (5.8 g).
3) 화합물 2의 합성3) Synthesis of Compound 2
중간체 2-1 (1.43 g, 4 mmol), 중간체 2-2 (4.48 g, 8.8 mmol), Pd(Pt-Bu3)2 (204 mg, 0.4 mmol)과 K2CO3 (2.76 g, 20 mmol)을 RBF에 넣고 N2 치환한다. THF (16 mL)와 H2O (4 mL)를 투입 후 90 oC에서 4시간 동안 교반한다. THF/brine work-up 후 유기층은 감압 하에 날려준다. CHCl3에 녹인 뒤 실리카 필터를 진행한다. EA re-slurry 정제하여 화합물 2 (3.7 g)을 확보하였다.Intermediate 2-1 (1.43 g, 4 mmol), Intermediate 2-2 (4.48 g, 8.8 mmol), Pd(P t -Bu 3 ) 2 (204 mg, 0.4 mmol) and K 2 CO 3 (2.76 g, 20 mmol) is added to RBF and N 2 is substituted. Add THF (16 mL) and H 2 O (4 mL) and stir at 90 o C for 4 hours. After THF/brine work-up, the organic layer is blown away under reduced pressure. Dissolve in CHCl 3 and proceed with silica filter. Compound 2 (3.7 g) was obtained through EA re-slurry purification.
화합물 2의 NMR 측정 값: 1H NMR (500 MHz, CDCl3) δ 8.23 - 8.20 (m, 2H), 8.00 - 7.98 (m, 2H), 7.96 - 7.88 (m, 10H), 7.78 (d, 4H), 7.64 - 7.61 (m, 8H) 7.61 - 7.57 (m, 4H), 7.51 - 7.41 (m, 14H), 7.33 (d, 2H), 2.36 - 2.31 (m, 12H)NMR measurements of compound 2: 1 H NMR (500 MHz, CDCl 3 ) δ 8.23 - 8.20 (m, 2H), 8.00 - 7.98 (m, 2H), 7.96 - 7.88 (m, 10H), 7.78 (d, 4H) ), 7.64 - 7.61 (m, 8H) 7.61 - 7.57 (m, 4H), 7.51 - 7.41 (m, 14H), 7.33 (d, 2H), 2.36 - 2.31 (m, 12H)
<제조예 3> - 화합물 3의 제조<Preparation Example 3> - Preparation of Compound 3
1) 중간체 3-1의 합성1) Synthesis of intermediate 3-1
1,4-dibromo-2,5-diethylbenzene (5.84 g, 20 mmol), B2pin2 (12.2 g, 48 mmol), PdCl2dppfCH2Cl2 (1.63 g, 2 mmol), KOAc (9.85 g, 100 mmol)을 RBF에 넣고 질소 치환한다. Dioxane (80 mL)에 녹인 용액을 투입 후 90 oC에서 밤새 교반한다. DCM/brine으로 work-up 후 유기층은 MgSO4로 물을 제거한 뒤 여과하였다. 여과액은 진공 건조한 뒤 MPLC 정제하여 중간체 3-1 (5.0 g)을 수득하였다.1,4-dibromo-2,5-diethylbenzene (5.84 g, 20 mmol), B 2 pin 2 (12.2 g, 48 mmol), PdCl 2 dppfCH 2 Cl 2 (1.63 g, 2 mmol), KOAc (9.85 g, 100 mmol) was added to RBF and purged with nitrogen. Add the solution dissolved in dioxane (80 mL) and stir at 90 o C overnight. After work-up with DCM/brine, the organic layer was filtered after removing water with MgSO 4 . The filtrate was dried under vacuum and purified by MPLC to obtain Intermediate 3-1 (5.0 g).
2) 중간체 3-2의 합성2) Synthesis of intermediate 3-2
SM-boronic acid (6.96 g, 20 mmol), Pd(PPh3)4 (1.16 g, 1 mmol), K2CO3 (8.3 g, 60 mmol)을 RBF에 넣고 질소로 치환한다. 2-Bromo-5-iodotoluene (3.68 mL, 26 mmol), THF (80 mL)와 H2O (20 mL)를 투입 후 90 oC에서 48시간 동안 교반한다. DCM/brine으로 work-up 후 유기층은 MgSO4로 물을 제거한 뒤 여과하였다. 여과액은 진공 건조한 뒤 MPLC 정제하여 중간체 3-2 (6 g)을 확보하였다.SM-boronic acid (6.96 g, 20 mmol), Pd(PPh 3 ) 4 (1.16 g, 1 mmol), and K 2 CO 3 (8.3 g, 60 mmol) were added to RBF and replaced with nitrogen. Add 2-Bromo-5-iodotoluene (3.68 mL, 26 mmol), THF (80 mL) and H 2 O (20 mL) and stir at 90 o C for 48 hours. After work-up with DCM/brine, the organic layer was filtered after removing water with MgSO 4 . The filtrate was vacuum dried and purified by MPLC to obtain Intermediate 3-2 (6 g).
3) 화합물 3의 합성3) Synthesis of Compound 3
중간체 3-1 (1.93 g, 5 mmol), 중간체 3-2 (5.21 g, 11 mmol), Pd(Pt-Bu3)2 (256 mg, 0.5 mmol)과 K2CO3 (3.46 g, 25 mmol)을 RBF에 넣고 N2 치환한다. THF (20 mL)와 H2O (5 mL)를 투입 후 90 oC에서 밤새 교반한다. DCM/brine work-up 후 유기 층은 감압 하에 날려준다. DCM/Hex 조건에서 MPLC 정제 후 DCM/EtOH 조건에서 침전 정제하여 화합물 3 (3.3 g)을 확보하였다.Intermediate 3-1 (1.93 g, 5 mmol), Intermediate 3-2 (5.21 g, 11 mmol), Pd(P t -Bu 3 ) 2 (256 mg, 0.5 mmol) and K 2 CO 3 (3.46 g, 25 mmol) is added to RBF and N 2 is substituted. Add THF (20 mL) and H 2 O (5 mL) and stir at 90 o C overnight. After DCM/brine work-up, the organic layer is blown away under reduced pressure. After MPLC purification under DCM/Hex conditions, compound 3 (3.3 g) was obtained by precipitation purification under DCM/EtOH conditions.
화합물 3의 NMR 측정 값: 1H NMR (500 MHz, CDCl3) δ 8.25 - 8.20 (m, 2H), 8.02 - 7.96 (m, 2H), 7.97 - 7.87 (m, 10H), 7.77 (d, 4H), 7.63 - 7.60 (m, 8H) 7.61 - 7.57 (m, 4H), 7.51 - 7.41 (m, 6H), 7.33 (d, 2H), 2.36 - 2.31 (m, 6H), 2.42 (q, 4H), 1.12 (t, 6H)NMR measurements of compound 3: 1 H NMR (500 MHz, CDCl 3 ) δ 8.25 - 8.20 (m, 2H), 8.02 - 7.96 (m, 2H), 7.97 - 7.87 (m, 10H), 7.77 (d, 4H) ), 7.63 - 7.60 (m, 8H) 7.61 - 7.57 (m, 4H), 7.51 - 7.41 (m, 6H), 7.33 (d, 2H), 2.36 - 2.31 (m, 6H), 2.42 (q, 4H) , 1.12 (t, 6H)
<실시예> - 유기 발광 소자의 제조<Example> - Manufacturing of organic light emitting device
[ITO 기판의 준비][Preparation of ITO substrate]
ITO(indium tin oxide)가 1,500Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이 때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀리포어사(Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후, 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. A glass substrate coated with a thin film of ITO (indium tin oxide) with a thickness of 1,500 Å was placed in distilled water with a detergent dissolved in it and washed ultrasonically. At this time, a detergent from Fischer Co. was used, and distilled water filtered secondarily using a filter from Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes.
증류수 세척이 끝난 후, 이소프로필, 아세톤의 용제로 초음파 세척을 하고 건조시킨 후, 상기 기판을 5분간 세정한 후 글로브박스로 기판을 수송시켰다.After washing with distilled water, the substrate was ultrasonic washed with a solvent such as isopropyl and acetone, dried, and then washed for 5 minutes before transporting the substrate to a glove box.
[소자예 1][Device example 1]
ITO 투명전극 위에 하기 화합물 A: 하기 p 도펀트(하기 화학식 E) (8:2의 중량비)의 2wt% 사이클로헥사논 잉크를 ITO 표면 위에 스핀코팅(4000rpm)하고 200℃ 에서 30분간 열처리하여 40nm 두께로 정공 주입층을 형성하였다. 이후 화합물 B을 톨루엔에 0.7 wt%로 용해시켜 상기 정공 주입층 위에 스핀 코팅하여 20nm로 성막하고 질소 분위기 하에서 200℃로 30분간 가열하여 정공 수송층을 형성하였다.On the ITO transparent electrode, Compound A: 2 wt% cyclohexanone ink containing the p dopant (Formula E below) (weight ratio of 8:2) was spin coated (4000 rpm) on the ITO surface and heat treated at 200°C for 30 minutes to form a 40 nm thick layer. A hole injection layer was formed. Afterwards, Compound B was dissolved in toluene at 0.7 wt%, spin-coated on the hole injection layer to form a 20 nm film, and heated at 200°C for 30 minutes under a nitrogen atmosphere to form a hole transport layer.
이어서, 상기 정공 수송층 위에 앞서 제조한 화합물 1에 화합물 C를 8%의 농도로 섞은 톨루엔 0.5 wt% 잉크를 스핀 코팅하여 20nm의 두께의 발광층을 형성하였다. 상기 발광층 위에 하기 화합물 D를 35nm의 두께로 진공 증착하여 전자 주입 및 전자 수송층을 형성하였다. 상기 전자 주입 및 수송층 위에 순차적으로 1nm 두께로 LiF와 100nm 두께로 알루미늄을 증착하여 캐소드를 형성하였다.Next, a 0.5 wt% toluene ink mixed with Compound 1 prepared previously and Compound C at a concentration of 8% was spin coated on the hole transport layer to form a light emitting layer with a thickness of 20 nm. Compound D below was vacuum deposited on the light emitting layer to a thickness of 35 nm to form an electron injection and electron transport layer. A cathode was formed by sequentially depositing LiF to a thickness of 1 nm and aluminum to a thickness of 100 nm on the electron injection and transport layer.
상기의 과정에서 유기물의 증착 속도는 0.4 내지 0.7 Å /sec를 유지하였고, 캐소드의 LiF는 0.3 Å/sec, 알루미늄은 2 Å /sec의 증착 속도를 유지하였으며, 증착시 진공도는 2 X 10-7 내지 5 X 10-8 torr를 유지하였다.In the above process, the deposition rate of organic materials was maintained at 0.4 to 0.7 Å/sec, LiF on the cathode was maintained at 0.3 Å/sec, aluminum was maintained at 2 Å/sec, and the vacuum degree during deposition was 2 to 5
[화합물 A][Compound A]
[화합물 B][Compound B]
[화합물 C][Compound C]
[화합물 D][Compound D]
[화학식 E][Formula E]
[소자예 2][Soja example 2]
상기 소자예 1의 제작과정에서 발광층 성막시 화합물 1에 화합물 C를 8%의 농도로 섞은 톨루엔 잉크 대신 화합물 2에 화합물 C를 8%의 농도로 섞은 톨루엔 잉크를 사용한 것을 제외하고는 소자예 1의 과정과 동일한 방법으로 유기 발광 소자를 제조하였다.In the manufacturing process of Device Example 1, except that when forming the emitting layer, toluene ink mixed with Compound 2 and Compound C at a concentration of 8% was used instead of toluene ink mixed with Compound 1 and Compound C at a concentration of 8%. An organic light emitting device was manufactured in the same manner as the process.
[소자예 3][Soja example 3]
상기 소자예 1의 제작과정에서 발광층 성막시 화합물 1에 화합물 C를 8%의 농도로 섞은 톨루엔 잉크 대신 화합물 3에 화합물 C를 8%의 농도로 섞은 톨루엔 잉크를 사용한 것을 제외하고는 소자예 1의 과정과 동일한 방법으로 유기 발광 소자를 제조하였다.In the manufacturing process of Device Example 1, except that when forming the light emitting layer, toluene ink mixed with Compound 3 and Compound C at a concentration of 8% was used instead of the toluene ink mixed with Compound 1 and Compound C at a concentration of 8%. An organic light emitting device was manufactured in the same manner as the process.
[비교 소자예 1][Comparative device example 1]
상기 소자예 1의 제작과정에서 발광층 성막시 화합물 1에 화합물 C를 8%의 농도로 섞은 톨루엔 잉크 대신 비교 화합물 1에 화합물 C를 8%의 농도로 섞은 톨루엔 잉크를 사용한 것을 제외하고는 소자예 1의 과정과 동일한 방법으로 유기 발광 소자를 제조하였다.In the manufacturing process of Device Example 1, except that when forming the emitting layer, toluene ink mixed with Compound 1 and Compound C at a concentration of 8% was used instead of toluene ink mixed with Compound 1 and Compound C at a concentration of 8%. An organic light emitting device was manufactured in the same manner as in the process.
[비교 화합물 1][Comparative Compound 1]
[비교 소자예 2][Comparative device example 2]
상기 소자예 1의 제작과정에서 발광층 성막시 화합물 1에 화합물 C를 8%의 농도로 섞은 톨루엔 잉크 대신 비교 화합물 2에 화합물 C를 8%의 농도로 섞은 톨루엔 잉크를 사용한 것을 제외하고는 소자예 1의 과정과 동일한 방법으로 유기 발광 소자를 제조하였다.In the manufacturing process of Device Example 1, except that when forming the emitting layer, toluene ink mixed with Compound 2 and Compound C at a concentration of 8% was used instead of toluene ink mixed with Compound 1 and Compound C at a concentration of 8%. An organic light emitting device was manufactured in the same manner as in the process.
[비교 화합물 2][Comparative Compound 2]
[비교 소자예 3][Comparative device example 3]
상기 소자예 1의 제작과정에서 발광층 성막시 화합물 1에 화합물 C를 8%의 농도로 섞은 톨루엔 잉크 대신 비교 화합물 3에 화합물 C를 8%의 농도로 섞은 톨루엔 잉크를 사용한 것을 제외하고는 소자예 1의 과정과 동일한 방법으로 유기 발광 소자를 제조하였다.In the manufacturing process of Device Example 1, except that toluene ink mixed with Compound 3 and Compound C at a concentration of 8% was used instead of toluene ink mixed with Compound 1 and Compound C at a concentration of 8% when forming the light emitting layer. An organic light emitting device was manufactured in the same manner as in the process.
[비교 화합물 3][Comparative Compound 3]
상기 소자예 1, 소자예 2, 소자예 3 및 비교 소자예 1, 비교 소자예 2, 비교 소자예 3에서 제조된 유기 발광 소자를 10 mA/cm2의 전류밀도에서 구동전압, 외부양자효율(external quantum efficiency), 휘도 및 수명을 측정한 결과를 하기 표 1에 나타내었다. 상기 외부양자효율은 (방출된 광자 수)/(주입된 전하운반체 수)로 구할 수 있고, T95는 10 mA/cm2의 전류밀도에서 초기 휘도 대비 95%가 되는 시간을 측정한 것이다. The organic light emitting devices manufactured in Device Example 1, Device Example 2, Device Example 3, and Comparative Device Example 1, Comparative Device Example 2 , and Comparative Device Example 3 were subjected to a driving voltage and external quantum efficiency ( The results of measuring external quantum efficiency, luminance, and lifespan are shown in Table 1 below. The external quantum efficiency can be calculated as (number of emitted photons)/(number of injected charge carriers), and T95 is measured as the time for 95% of initial luminance at a current density of 10 mA/cm 2 .
상기 표 1에서 보는 바와 같이, 본 명세서의 화학식 1로 표시되는 화합물을 사용한 소자예 1, 2 및 3의 유기 발광 소자는 비교 소자예 1 내지 3에 비하여 고효율 및 장수명의 특성을 보이며, 유기 발광 소자에 적용 가능함을 확인할 수 있다.As shown in Table 1, the organic light-emitting devices of Device Examples 1, 2, and 3 using the compound represented by Formula 1 of the present specification show high efficiency and long lifespan compared to Comparative Device Examples 1 to 3, and the organic light-emitting devices You can confirm that it is applicable.
구체적으로, 본 명세서의 화학식 1로 표시되는 화합물을 유기 발광 소자의 발광층 호스트로 사용한 경우, 비교 소자예 1 내지 3에 비하여, 용해성이 향상되고, 막의 안정성도 우수한 것을 알 수 있다. 특히, 증착용 재료로 사용되는 비교 화합물 1 및 2에 비해서는 용해도 및 막 안정성이 월등하여 수명 증가가 크게 나타났다.Specifically, when the compound represented by Formula 1 of the present specification is used as the light-emitting layer host of an organic light-emitting device, it can be seen that the solubility is improved and the stability of the film is excellent compared to Comparative Device Examples 1 to 3. In particular, compared to Comparative Compounds 1 and 2 used as deposition materials, the solubility and film stability were superior, resulting in a significant increase in lifespan.
이상을 통해, 본 명세서의 바람직한 실시예에 대하여 설명하였지만, 본 발명은 이에 한정되는 것이 아니고 특허청구범위와 발명의 상세한 설명의 범위 안에서 여러 가지로 변형하여 실시하는 것이 가능하고 이 또한 발명의 범주에 속한다.Although the preferred embodiments of the present specification have been described above, the present invention is not limited thereto, and can be implemented with various modifications within the scope of the claims and the detailed description of the invention, and this is also within the scope of the invention. It belongs.
1: 기판 2: 양극
3: 발광층 4: 음극
5: 정공주입층 6: 정공수송층
7: 발광층 8: 전자수송층1: Substrate 2: Anode
3: light emitting layer 4: cathode
5: hole injection layer 6: hole transport layer
7: light emitting layer 8: electron transport layer
Claims (9)
[화학식 1]
상기 화학식 1에서,
Ar1 및 Ar2는 각각 독립적으로 C1-10 알킬로 치환 또는 비치환된 C6-60 아릴렌이고,
Ar3 및 Ar4는 각각 독립적으로 C1-10 알킬로 치환 또는 비치환된 C6-60 아릴이고,
n은 각각 독립적으로 0 내지 4의 정수이며,
Q는 각각 독립적으로 수소; 또는 C1-60 알킬이고,
L은 하기 화학식 2 또는 3으로 표시되는 치환기이며,
[화학식 2]
[화학식 3]
상기 화학식 2 및 3에서,
R1 내지 R4는 각각 독립적으로 C1-60 알킬이고,
R5 내지 R12는 각각 독립적으로 수소; 또는 C1-60 알킬이다.
Compound represented by Formula 1:
[Formula 1]
In Formula 1,
Ar 1 and Ar 2 are each independently C 6-60 arylene unsubstituted or substituted with C 1-10 alkyl,
Ar 3 and Ar 4 are each independently C 6-60 aryl substituted or unsubstituted with C 1-10 alkyl,
n is each independently an integer from 0 to 4,
Q is each independently hydrogen; or C 1-60 alkyl,
L is a substituent represented by the following formula 2 or 3,
[Formula 2]
[Formula 3]
In Formulas 2 and 3,
R 1 to R 4 are each independently C 1-60 alkyl,
R 5 to R 12 are each independently hydrogen; or C 1-60 alkyl.
R1 내지 R4는 각각 독립적으로 C1-10 알킬인, 화합물.
According to paragraph 1,
A compound wherein R 1 to R 4 are each independently C 1-10 alkyl.
R5 내지 R12는 각각 독립적으로 수소; 또는 C1-10 알킬인, 화합물.
According to paragraph 1,
R 5 to R 12 are each independently hydrogen; or C 1-10 alkyl, a compound.
Ar1 및 Ar2는 각각 독립적으로, 하기로 구성되는 군으로부터 선택되는 어느 하나인, 화합물:
상기 화학식에서 R20은 수소 또는 C1-10 알킬이다.
According to paragraph 1,
Ar 1 and Ar 2 are each independently any one selected from the group consisting of:
In the above formula, R 20 is hydrogen or C 1-10 alkyl.
Ar3 및 Ar4는 각각 독립적으로, 하기로 구성되는 군으로부터 선택되는 어느 하나인, 화합물:
상기 화학식에서 R21은 수소 또는 C1-10 알킬이다.
According to paragraph 1,
Ar 3 and Ar 4 are each independently any one selected from the group consisting of:
In the above formula, R 21 is hydrogen or C 1-10 alkyl.
n은 각각 독립적으로 0 내지 2의 정수이며,
Q는 각각 독립적으로 수소; 또는 C1-10 알킬인, 화합물
According to paragraph 1,
n is each independently an integer from 0 to 2,
Q is each independently hydrogen; or C 1-10 alkyl, a compound
상기 화학식 1로 표시되는 화합물은 하기 화합물로 구성되는 군으로부터 선택되는 어느 하나인, 화합물:
According to paragraph 1,
The compound represented by Formula 1 is any one selected from the group consisting of the following compounds:
first electrode; a second electrode provided opposite to the first electrode; And an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound according to any one of claims 1 to 7. An organic light-emitting device.
상기 화합물을 포함하는 유기물층은 발광층인 것을 특징으로 하는, 유기 발광 소자.
According to clause 8,
An organic light-emitting device, wherein the organic layer containing the compound is a light-emitting layer.
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