WO2017142310A1 - Heterocyclic compound and organic electroluminescent device comprising same - Google Patents
Heterocyclic compound and organic electroluminescent device comprising same Download PDFInfo
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- WO2017142310A1 WO2017142310A1 PCT/KR2017/001655 KR2017001655W WO2017142310A1 WO 2017142310 A1 WO2017142310 A1 WO 2017142310A1 KR 2017001655 W KR2017001655 W KR 2017001655W WO 2017142310 A1 WO2017142310 A1 WO 2017142310A1
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- Prior art keywords
- group
- substituted
- unsubstituted
- compound
- heterocyclic
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 34
- -1 dibenzofuranyl group Chemical group 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 45
- 238000002347 injection Methods 0.000 claims description 43
- 239000007924 injection Substances 0.000 claims description 43
- 239000011368 organic material Substances 0.000 claims description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 230000005525 hole transport Effects 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 230000000903 blocking effect Effects 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000006267 biphenyl group Chemical group 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 7
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- CRXBTDWNHVBEIC-UHFFFAOYSA-N 1,2-dimethyl-9h-fluorene Chemical group C1=CC=C2CC3=C(C)C(C)=CC=C3C2=C1 CRXBTDWNHVBEIC-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 5
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 claims description 5
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000005580 triphenylene group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical compound [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 141
- 230000000052 comparative effect Effects 0.000 description 43
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- 0 C(C1C=CC=C2)C12c1ccc2-c3cccc(-c(cc4)ccc4N(c(cc4)ccc4-c4ccccc4)c(cc4)c5c6c4c4ccccc4[n]6c4c5cccc4)c3**c2c1 Chemical compound C(C1C=CC=C2)C12c1ccc2-c3cccc(-c(cc4)ccc4N(c(cc4)ccc4-c4ccccc4)c(cc4)c5c6c4c4ccccc4[n]6c4c5cccc4)c3**c2c1 0.000 description 17
- SFFSGPCYJCMDJM-UHFFFAOYSA-N 2-[2-(3-oxo-1,2-benzoselenazol-2-yl)ethyl]-1,2-benzoselenazol-3-one Chemical compound [se]1C2=CC=CC=C2C(=O)N1CCN1C(=O)C(C=CC=C2)=C2[se]1 SFFSGPCYJCMDJM-UHFFFAOYSA-N 0.000 description 15
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
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- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
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- 125000003545 alkoxy group Chemical group 0.000 description 3
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- 239000010405 anode material Substances 0.000 description 3
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- 229940125904 compound 1 Drugs 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- SZLNOBJKCVERBJ-UHFFFAOYSA-N 1-azapentacyclo[10.6.1.02,7.08,19.013,18]nonadeca-2,4,6,8(19),9,11,13,15,17-nonaene Chemical compound C12=CC=CC=C2N2C3=CC=CC=C3C3=CC=CC1=C32 SZLNOBJKCVERBJ-UHFFFAOYSA-N 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
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- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
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- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 2
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- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
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- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
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- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
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- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 2
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- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
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Images
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
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Definitions
- Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
- L1 to L3 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
- the present application is a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the aforementioned heterocyclic compound. do.
- FIG. 1 illustrates an example of an organic electroluminescent device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked.
- FIG. 2 illustrates an organic electroluminescent device in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7 and a cathode 4 are sequentially stacked. An example is shown.
- Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
- L1 is a direct bond; Phenylene group; Divalent dibenzofuranyl group; Divalent dibenzothiophenyl group; Divalent fluorenyl group; Or a divalent dimethylfluorenyl group.
- L2 and L3 are the same as or different from each other, and each independently a direct bond or a phenylene group.
- the two or more organic material layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer simultaneously performing electron transport and electron injection, and a hole blocking layer.
- the organic material layers may be formed of the same material or different materials.
- the organic EL device of the present application may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
- a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation
- a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode.
- 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.
- an organic EL device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
- the compound of Formula 1 may be formed of an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic EL device.
- the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
- the electron transporting material is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
- the electron transporting material is a material that can inject electrons well from the cathode and move them to the light emitting layer. This is suitable. Specific examples thereof include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
- the electron transport layer can be used with any desired cathode material as used in accordance with the prior art.
- suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.
- fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
- An organic electroluminescent device was manufactured in the same manner as in Comparative Example, except that the compound of H-6 was used instead of the compound EB in the comparative example.
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Abstract
The present specification provides a heterocyclic compound and an organic electroluminescent device comprising same.
Description
본 명세서는 헤테로고리 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것이다.The present specification relates to a heterocyclic compound and an organic electroluminescent device including the same.
본 명세서는 2016년 2월 15일에 한국특허청에 제출된 한국특허 출원 제10-2016-0017271호의 출원일의 이익을 주장하며, 그 내용은 전부 본 명세서에 포함된다. This specification claims the benefit of the filing date of Korean Patent Application No. 10-2016-0017271 filed with the Korea Intellectual Property Office on February 15, 2016, the contents of which are incorporated in full herein.
전계 발광 소자는 자체 발광형 표시 소자의 일종으로서, 시야각이 넓고, 콘트라스트가 우수할 뿐만 아니라 응답속도가 빠르다는 장점을 가지고 있다. The electroluminescent device is a kind of self-luminous display device, and has an advantage of having a wide viewing angle, excellent contrast, and fast response speed.
유기발광소자는 2개의 전극 사이에 유기박막을 배치시킨 구조를 가지고 있다. 이와 같은 구조의 유기발광소자에 전압이 인가되면, 2개의 전극으로부터 주입된 전자와 정공이 유기박막에서 결합하여 쌍을 이룬 후 소멸하면서 빛을 발하게 된다. 상기 유기박막은 필요에 따라 단층 또는 다층으로 구성될 수 있다. The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from two electrodes are combined in the organic thin film to form a pair, then disappear and emit light. The organic thin film may be composed of a single layer or multiple layers as necessary.
유기박막의 재료는 필요에 따라 발광 기능을 가질 수 있다. 예컨대, 유기박막 재료로는 그 자체가 단독으로 발광층을 구성할 수 있는 화합물이 사용될 수도 있고, 또는 호스트-도펀트계 발광층의 호스트 또는 도펀트 역할을 할 수 있는 화합물이 사용될 수도 있다. 그 외에도, 유기박막의 재료로서, 정공주입, 정공수송, 전자블록킹, 정공블록킹, 전자수송 또는 전자주입 등의 역할을 수행할 수 있는 화합물이 사용될 수도 있다.The material of the organic thin film may have a light emitting function as necessary. For example, as the organic thin film material, a compound which may itself constitute a light emitting layer may be used, or a compound which may serve as a host or a dopant of a host-dopant-based light emitting layer may be used. In addition, as a material of the organic thin film, a compound capable of performing a role such as hole injection, hole transport, electron blocking, hole blocking, electron transport or electron injection may be used.
유기 전계 발광 소자의 성능, 수명 또는 효율을 향상시키기 위하여, 유기박막의 재료의 개발이 지속적으로 요구되고 있다.In order to improve the performance, lifespan or efficiency of an organic electroluminescent element, development of the material of an organic thin film is continuously required.
본 명세서는 헤테로고리 화합물 및 이를 포함하는 유기 전계 발광 소자를 제공한다.The present specification provides a heterocyclic compound and an organic electroluminescent device including the same.
본 출원은 하기 화학식 1로 표시되는 헤테로고리 화합물을 제공한다.The present application provides a heterocyclic compound represented by the following formula (1).
[화학식 1] [Formula 1]
상기 화학식 1에 있어서, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고, In Formula 1, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
L1 내지 L3는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 2가의 헤테로고리기이며, L1 to L3 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
R1 내지 R3는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고, a는 0 내지 2의 정수이고, b 및 c는 0 내지 4의 정수이며, a 내지 c가 2 이상인 경우 괄호안의 치환기는 같거나 상이하다. R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group, a is an integer of 0 to 2, b and c are integers of 0 to 4, and when a to c are 2 or more, the substituents in parentheses are the same or different.
또한, 본 출원은 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 유기물층 중 1 층 이상은 전술한 헤테로고리 화합물을 포함하는 것인 유기 전계 발광 소자를 제공한다.In addition, the present application is a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the aforementioned heterocyclic compound. do.
본 출원의 일 실시상태에 따른 헤테로고리 화합물은 유기 전계 발광 소자에 사용되어, 유기 전계 발광 소자의 구동전압을 낮추고, 광효율을 향상시키며, 화합물의 열적 안정성에 의하여 소자의 수명 특성을 향상시킬 수 있다. The heterocyclic compound according to the exemplary embodiment of the present application may be used in an organic electroluminescent device to lower the driving voltage of the organic electroluminescent device, improve light efficiency, and improve the lifetime characteristics of the device by thermal stability of the compound. .
도 1은 기판(1), 양극(2), 발광층(3), 음극(4)이 순차적으로 적층된 유기 전계 발광 소자의 예를 도시한 것이다. 1 illustrates an example of an organic electroluminescent device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked.
도 2는 기판 (1), 양극(2), 정공주입층(5), 정공수송층(6), 발광층(3), 전자수송층(7) 및 음극(4)이 순차적으로 적층된 유기 전계 발광 소자의 예를 도시한 것이다. 2 illustrates an organic electroluminescent device in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7 and a cathode 4 are sequentially stacked. An example is shown.
도 3은 반응식 1의 화학식 1-c의 LC/MS 스펙트럼이다.3 is an LC / MS spectrum of Formula 1-c of Scheme 1.
도 4는 반응식 1의 화학식 1A의 LC/MS 스펙트럼이다.4 is an LC / MS spectrum of Formula 1A of Scheme 1. FIG.
도 5는 합성예 2의 화합물 2의 LC/MS 스펙트럼이다.5 is an LC / MS spectrum of Compound 2 of Synthesis Example 2. FIG.
도 6은 합성예 3의 화합물 3의 LC/MS 스펙트럼이다.6 is an LC / MS spectrum of Compound 3 of Synthesis Example 3. FIG.
도 7은 합성예 5의 화합물 5의 LC/MS 스펙트럼이다.7 is LC / MS spectrum of Compound 5 of Synthesis Example 5. FIG.
[부호의 설명][Description of the code]
1: 기판1: substrate
2: 양극2: anode
3: 발광층3: light emitting layer
4: 음극4: cathode
5: 정공주입층5: hole injection layer
6: 정공수송층6: hole transport layer
7: 전자수송층 7: electron transport layer
이하, 본 명세서에 대하여 더욱 상세하게 설명한다.Hereinafter, this specification is demonstrated in detail.
본 명세서는 상기 화학식 1로 표시되는 헤테로고리 화합물을 제공한다.The present specification provides a heterocyclic compound represented by Chemical Formula 1.
본 명세서에서 치환기의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다. Examples of substituents herein are described below, but are not limited thereto.
상기 "치환"이라는 용어는 화합물의 탄소 원자에 결합된 수소 원자가 다른 치환기로 바뀌는 것을 의미하며, 치환되는 위치는 수소 원자가 치환되는 위치 즉, 치환기가 치환 가능한 위치라면 한정하지 않으며, 2 이상 치환되는 경우, 2 이상의 치환기는 서로 동일하거나 상이할 수 있다.The term "substituted" means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 시아노기; 니트로기; 히드록시기; 알킬기; 시클로알킬기; 알케닐기; 알콕시기; 아릴기; 및 헤테로고리기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되었거나 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 바이페닐기일 수 있다. 즉, 바이페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 있다. As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Cyano group; Nitro group; Hydroxyl group; An alkyl group; Cycloalkyl group; Alkenyl groups; An alkoxy group; Aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group or substituted with a substituent to which two or more substituents in the above-described substituents are connected, or does not have any substituents. For example, "a substituent to which two or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다. In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 50인 것이 바람직하다. 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, 시클로펜틸메틸, 시클로헥실메틸, 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 linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 50. Specific examples 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-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like.
본 명세서에 있어서, 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 구체적으로 시클로프로필, 시클로부틸, 시클로펜틸, 3-메틸시클로펜틸, 2,3-디메틸시클로펜틸, 시클로헥실, 3-메틸시클로헥실, 4-메틸시클로헥실, 2,3-디메틸시클로헥실, 3,4,5-트리메틸시클로헥실, 4-tert-부틸시클로헥실, 시클로헵틸, 시클로옥틸 등이 있으나, 이에 한정되지 않는다. In the present specification, the cycloalkyl group is not particularly limited, but preferably 3 to 60 carbon atoms, specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto. Do not.
본 명세서에 있어서, 상기 알콕시기는 직쇄, 분지쇄 또는 고리쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 20인 것이 바람직하다. 구체적으로, 메톡시, 에톡시, n-프로폭시, 이소프로폭시, n-부톡시, 이소부톡시, tert-부톡시, sec-부톡시, n-펜틸옥시, 네오펜틸옥시, 이소펜틸옥시, n-헥실옥시, 3,3-디메틸부틸옥시, 2-에틸부틸옥시, n-옥틸옥시, n-노닐옥시, n-데실옥시, 벤질옥시, p-메틸벤질옥시 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -Hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, and the like. It is not limited.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 40인 것이 바람직하다. 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 linear or branched chain, the carbon number is not particularly limited, but is preferably 2 to 40. 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 and the like, but are not limited thereto.
본 명세서에서 상기 아릴기가 단환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나, 탄소수 6 내지 25인 것이 바람직하다. 구체적으로 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. In the present specification, when the aryl group is a monocyclic aryl group, carbon number is not particularly limited, but preferably 6 to 25 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
상기 아릴기가 다환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나. 탄소수 10 내지 24인 것이 바람직하다. 구체적으로 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트릴기, 파이레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-24. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
본 명세서에 있어서, 상기 플루오레닐기는 치환될 수 있으며, 인접한 치환기들이 서로 결합하여 고리를 형성할 수 있다.In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
상기 플루오레닐기가 치환되는 경우,
, 
등이 될 수 있으나, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted, , Etc., but is not limited thereto.
본 명세서에 있어서, 헤테로고리기는 탄소가 아닌 원자, 이종원자를 1 이상 포함하는 것으로서, 구체적으로 상기 이종 원자는 O, N, Se 및 S 등으로 이루어진 군에서 선택되는 원자를 1 이상 포함할 수 있다. 헤테로고리기의 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 60인 것이 바람직하다. 헤테로고리기의 예로는 티오페닐기, 퓨라닐기, 피롤기, 이미다졸릴기, 티아졸릴기, 옥사졸릴기, 옥사디아졸릴기, 트리아졸릴기, 피리딜기, 비피리딜기, 피리미딜기, 트리아지닐기, 아크리딜기, 하이드로아크리딜기(예컨대, 
), 피리다지닐기, 피라지닐기, 퀴놀리닐기, 퀴나졸리닐기, 퀴녹살리닐기, 프탈라지닐기, 피리도피리미디닐기, 피리도피라지닐기, 피라지노피라지닐기, 이소퀴놀리닐기, 인돌기, 카바졸릴기, 벤즈옥사졸릴기, 벤즈이미다졸릴기, 벤조티아졸릴기, 벤조카바졸릴기, 디벤조카바졸릴기, 벤조티오페닐기, 디벤조티오페닐기, 벤조퓨라닐기, 디벤조퓨라닐기; 벤조실롤기; 디벤조실롤기; 페난트롤리닐기(phenanthrolinyl group), , 이소옥사졸릴기, 티아디아졸릴기, 페노티아지닐기, 페노옥사지닐기, 및 이들의 축합구조 등이 있으나, 이들에만 한정되는 것은 아니다. 이외에도 헤테로고리기의 예로서, 술포닐기를 포함하는 헤테로고리 구조, 예컨대, 
등이 있다.In the present specification, the heterocyclic group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. Although carbon number of a heterocyclic group is not specifically limited, It is preferable that it is C2-C60. Examples of the heterocyclic group include thiophenyl group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, triazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl Groups, acridil groups, hydroacridyl groups (e.g., ), Pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, and isoquinolinyl , Indole group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, benzothiophenyl group, dibenzothiophenyl group, benzofuranyl group, dibenzo Furanyl group; Benzosilol group; Dibenzosilol group; Phenanthrolinyl group,, isooxazolyl group, thiadiazolyl group, phenothiazinyl group, phenooxazinyl group, and condensation structures thereof, and the like, but are not limited thereto. In addition, examples of heterocyclic groups include heterocyclic structures including a sulfonyl group, for example, Etc.
본 명세서에 있어서, 상기 축합구조는 해당 치환기에 방향족 탄소수소 고리가 축합된 구조일 수 있다. 예컨대, 벤즈이미다졸의 축합고리로서 
등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the condensation structure may be a structure in which an aromatic carbon hydrogen ring is condensed to a corresponding substituent. For example, as a condensed ring of benzimidazole Etc., but is not limited thereto.
본 명세서에 있어서, 아릴렌기는 아릴기에 결합 위치가 두 개 있는 것 즉 2가기를 의미한다. 이들은 각각 2가기인 것을 제외하고는 전술한 아릴기의 설명이 적용될 수 있다.In the present specification, the arylene group refers to a divalent group having two bonding positions in the aryl group. The description of the aforementioned aryl group can be applied except that they are each divalent.
본 명세서에 있어서, "인접한" 기는 해당 치환기가 치환된 원자와 직접 연결된 원자에 치환된 치환기 또는 해당 치환기가 치환된 원자에 치환된 다른 치환기를 의미할 수 있다. 예컨대, 벤젠고리에서 오쏘(ortho)위치로 치환된 2개의 치환기 및 지방족 고리에서 동일 탄소에 치환된 2개의 치환기는 서로 "인접한" 기로 해석될 수 있다.In the present specification, "adjacent" group may mean a substituent substituted on an atom directly connected to an atom in which the corresponding substituent is substituted or another substituent substituted on an atom in which the substituent is substituted. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" groups.
본 명세서의 일 실시상태에 있어서, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로고리기이다.In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
본 명세서의 일 실시상태에 있어서, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 20의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기이다.In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 비페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 트리페닐렌기; 치환 또는 비치환된 디메틸플루오렌기; 치환 또는 비치환된 디벤조퓨란기; 치환 또는 비치환된 디벤조티오펜기; 또는 치환 또는 비치환된 카바졸기이다. In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted triphenylene group; Substituted or unsubstituted dimethyl fluorene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted carbazole group.
본 명세서의 일 실시상태에 있어서, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 아릴기로 치환 또는 비치환된 페닐기; 아릴기로 치환 또는 비치환된 비페닐기; 아릴기로 치환 또는 비치환된 터페닐기; 아릴기로 치환 또는 비치환된 트리페닐렌기; 아릴기로 치환 또는 비치환된 디메틸플루오렌기; 아릴기로 치환 또는 비치환된 디벤조퓨란기; 아릴기로 치환 또는 비치환된 디벤조티오펜기; 또는 아릴기로 치환 또는 비치환된 카바졸기이다. In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an aryl group; A biphenyl group unsubstituted or substituted with an aryl group; Terphenyl group unsubstituted or substituted with an aryl group; Triphenylene group unsubstituted or substituted with an aryl group; Dimethyl fluorene group unsubstituted or substituted with an aryl group; Dibenzofuran group unsubstituted or substituted with an aryl group; Dibenzothiophene group unsubstituted or substituted with an aryl group; Or a carbazole group unsubstituted or substituted with an aryl group.
본 명세서의 일 실시상태에 있어서, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 페닐기로 치환 또는 비치환된 페닐기; 페닐기로 치환 또는 비치환된 비페닐기; 페닐기로 치환 또는 비치환된 터페닐기; 페닐기로 치환 또는 비치환된 트리페닐렌기; 페닐기로 치환 또는 비치환된 디메틸플루오렌기; 페닐기로 치환 또는 비치환된 디벤조퓨란기; 페닐기로 치환 또는 비치환된 디벤조티오펜기; 또는 페닐기로 치환 또는 비치환된 카바졸기이다. In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a phenyl group; A biphenyl group unsubstituted or substituted with a phenyl group; Terphenyl group unsubstituted or substituted with a phenyl group; Triphenylene group unsubstituted or substituted with a phenyl group; Dimethyl fluorene group unsubstituted or substituted with a phenyl group; Dibenzofuran group unsubstituted or substituted with a phenyl group; Dibenzothiophene group unsubstituted or substituted with a phenyl group; Or a carbazole group unsubstituted or substituted with a phenyl group.
본 명세서의 일 실시상태에 있어서, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 페닐기로 치환 또는 비치환된 페닐기; 비페닐기; 터페닐기; 트리페닐렌기; 페닐기로 치환 또는 비치환된 디메틸플루오렌기; 페닐기로 치환 또는 비치환된 디벤조퓨란기; 페닐기로 치환 또는 비치환된 디벤조티오펜기; 또는 페닐기로 치환 또는 비치환된 카바졸기이다.In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a phenyl group; Biphenyl group; Terphenyl group; Triphenylene group; Dimethyl fluorene group unsubstituted or substituted with a phenyl group; Dibenzofuran group unsubstituted or substituted with a phenyl group; Dibenzothiophene group unsubstituted or substituted with a phenyl group; Or a carbazole group unsubstituted or substituted with a phenyl group.
본 명세서의 일 실시상태에 있어서, L1은 직접결합; 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 2가의 헤테로고리기이다.In one embodiment of the present specification, L1 is a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted divalent heterocyclic group having 2 to 60 carbon atoms.
본 명세서의 일 실시상태에 있어서, L1은 직접결합; 치환 또는 비치환된 탄소수 6 내지 20의 아릴렌기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 2가의 헤테로고리기이다.In one embodiment of the present specification, L1 is a direct bond; A substituted or unsubstituted arylene group having 6 to 20 carbon atoms; Or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, L1은 직접결합; 치환 또는 비치환된 페닐렌기; 치환 또는 비치환된 2가의 디벤조퓨라닐기; 치환 또는 비치환된 2가의 디벤조티오페닐기; 또는 치환 또는 비치환된 2가의 플루오레닐기이다.In one embodiment of the present specification, L1 is a direct bond; Substituted or unsubstituted phenylene group; A substituted or unsubstituted divalent dibenzofuranyl group; A substituted or unsubstituted divalent dibenzothiophenyl group; Or a substituted or unsubstituted divalent fluorenyl group.
본 명세서의 일 실시상태에 있어서, L1은 직접결합; 알킬기로 치환 또는 비치환된 페닐렌기; 알킬기로 치환 또는 비치환된 2가의 디벤조퓨라닐기; 알킬기로 치환 또는 비치환된 2가의 디벤조티오페닐기; 또는 알킬기로 치환 또는 비치환된 2가의 플루오레닐기이다.In one embodiment of the present specification, L1 is a direct bond; A phenylene group unsubstituted or substituted with an alkyl group; Divalent dibenzofuranyl group unsubstituted or substituted with an alkyl group; Divalent dibenzothiophenyl group unsubstituted or substituted with an alkyl group; Or a divalent fluorenyl group unsubstituted or substituted with an alkyl group.
본 명세서의 일 실시상태에 있어서, L1은 직접결합; 페닐렌기; 2가의 디벤조퓨라닐기; 2가의 디벤조티오페닐기; 2가의 플루오레닐기; 또는 2가의 디메틸플루오레닐기이다.In one embodiment of the present specification, L1 is a direct bond; Phenylene group; Divalent dibenzofuranyl group; Divalent dibenzothiophenyl group; Divalent fluorenyl group; Or a divalent dimethylfluorenyl group.
본 명세서의 일 실시상태에 있어서, L2 및 L3은 서로 동일하거나 상이하고, 각각 독립적으로 직접결합 또는 치환 또는 비치환된 아릴렌기이다.In one embodiment of the present specification, L2 and L3 are the same as or different from each other, and each independently a direct bond or a substituted or unsubstituted arylene group.
본 명세서의 일 실시상태에 있어서, L2 및 L3은 서로 동일하거나 상이하고, 각각 독립적으로 직접결합 또는 아릴렌기이다.In one embodiment of the present specification, L2 and L3 are the same as or different from each other, and each independently a direct bond or an arylene group.
본 명세서의 일 실시상태에 있어서, L2 및 L3은 서로 동일하거나 상이하고, 각각 독립적으로 직접결합 또는 페닐렌기이다.In one embodiment of the present specification, L2 and L3 are the same as or different from each other, and each independently a direct bond or a phenylene group.
본 명세서의 일 실시상태에 있어서, R1 내지 R3은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 또는 중수소이다. In one embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; Or deuterium.
본 명세서의 일 실시상태에 있어서, R1 내지 R3은 수소이다. In one embodiment of the present specification, R1 to R3 are hydrogen.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 화합물은 하기 구조식들 중에서 선택되는 어느 하나이다. In one embodiment of the present specification, the compound represented by Formula 1 is any one selected from the following structural formulas.
본 명세서의 일 실시상태에 따른 화합물은 후술하는 제조방법으로 제조될 수 있다. Compounds according to one embodiment of the present specification may be prepared by the preparation method described below.
[반응식 1] Scheme 1
1) 화학식 1-c의 제조1) Preparation of Chemical Formula 1-c
4-브로모-1-클로로-2-아이오도벤젠 200.00 g (1.00 eq), (2-나이트로페닐)브로닉 에시드((2-nitrophenyl)boronic acid) 105.78 g (1.0 eq), Pd(PPh3)4 7.31 g (0.01 eq) 를 THF 1.5L 에 녹여 교반한 다음 K2CO3 113.78 g (1.3 eq)를 물 400 ml 에 녹여 첨가 이를 60℃에서 교반했다. 2시간 후 반응이 종료되면 유기층을 분리한 뒤 감압하여 용매를 제거했다. 생성물을 CHCl3에 완전히 녹인 후 물로 씻어주고 용액을 50% 정도 감압 농축하고 에탄올을 넣어서 결정을 떨어트리고 여과했다. 이 후 컬럼크로마토그래피를 이용하여 정제했다. 화학식 1-c를 171.30 g (수율 87 %) 얻었다. [M+H]=310200.00 g (1.00 eq) of 4-bromo-1-chloro-2-iodobenzene, (2-nitrophenyl) boronic acid 105.78 g (1.0 eq), Pd (PPh 3 ) 4 7.31 g (0.01 eq) was dissolved in 1.5 L of THF and stirred, and 113.78 g (1.3 eq) of K 2 CO 3 was dissolved in 400 ml of water, which was then stirred at 60 ° C. After the reaction was completed after 2 hours, the organic layer was separated, and the solvent was removed under reduced pressure. The product was completely dissolved in CHCl 3 , washed with water, the solution was concentrated under reduced pressure by 50%, ethanol was added, and the crystals were dropped and filtered. Then, the purification was performed using column chromatography. 171.30 g (yield 87%) of Formula 1-c were obtained. [M + H] = 310
2) 화학식 1-b의 제조2) Preparation of Chemical Formula 1-b
화학식 1-c 171.30 g (1.0 eq)를 트라이에틸포스파이트 (P(OEt) 3) 500mL 에 녹여 환류하여 교반했다. 3시간 후 반응이 종료되면 진공 감압하여 50% 정도의 용매를 제거하고 식혀서 결정을 떨어트렸다. 여과 후 에틸 아세테이트에 완전히 녹인 후 물로 씻어주고 용액을 70% 정도 감압 농축하고 식혀서 결정을 떨어 트리고 여과했다. 이 후 컬럼크로마토그래피를 이용하여 정제했다. 화학식 1-b를 124.48 g (수율 81 %) 얻었다. [M+H]=279171.30 g (1.0 eq) of Chemical Formula 1-c was dissolved in 500 mL of triethyl phosphite (P (OEt) 3 ) and refluxed to stir. After 3 hours, when the reaction was completed, the resulting mixture was cooled under vacuum to remove about 50% of the solvent and cooled to drop crystals. After filtration, the solution was dissolved in ethyl acetate and washed with water. The solution was concentrated under reduced pressure at 70%, cooled, and dropped crystals. Then, the purification was performed using column chromatography. 124.48 g (yield 81%) of formula 1-b were obtained. [M + H] = 279
3) 화학식 1-a의 제조3) Preparation of Chemical Formula 1-a
화학식 1-b 124.48 g (1.0 eq), 아이오도벤젠 100.10 g (1.1 eq), CuI 25.49 g (0.3 eq), K2CO3 12.34 g (2.0 eq)을 디옥산 1L에 넣고 에틸렌디아민 30ml를 적가하고 80℃ 에서 교반했다. 반응이 종료되면 상온으로 식힌 뒤 생성물 이 녹아 있는 용액을 감압하여 용매를 모두 제거해 준 뒤, CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 제거하고 이를 컬럼크로마토그래피를 이용하여 정제했다. 화학식 1-a을 123.56 g (수율 78 %) 얻었다. [M+H]=355124.48 g (1.0 eq) of Formula 1-b, 100.10 g (1.1 eq) of iodobenzene, 25.49 g (0.3 eq) of CuI, 12.34 g (2.0 eq) of K 2 CO 3 are added to 1 L of dioxane and 30 ml of ethylenediamine is added dropwise. And stirred at 80 ° C. After the reaction was completed, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure to remove all solvents. Then, the solvent was completely dissolved in CHCl 3 , washed with water, and removed under reduced pressure to remove the solvent, which was then purified by column chromatography. 123.56 g (yield 78%) of Formula 1-a were obtained. [M + H] = 355
4) 화학식 1A의 제조4) Preparation of Chemical Formula 1A
화학식 1-a 123.55 g (1.0 eq) 에 Pd(t-Bu3P)2
0.75 g (0.005 eq), K2CO3 126.05 g (2.00 eq) 을 다이메틸아세트아마이드 (Dimethylacetamide) 800mL에 넣고 환류하여 교반했다. 3시간 후 반응물을 물에 부어서 결정을 떨어트리고 여과했다. 여과한 고체를 에틸 아세테이트에 완전히 녹인 후 물로 씻어주고 생성물이 녹아있는 용액을 감압 농축하고 컬럼크로마토그래피를 이용하여 정제했다. 화학식 1A를 86.90 g (수율 83 %) 얻었다. [M]=275123.55 g (1.0 eq) in Pd (t-Bu 3 P) 2 0.75 g (0.005 eq) and 126.05 g (2.00 eq) of K 2 CO 3 were added to 800 mL of dimethylacetamide, and the mixture was refluxed and stirred. After 3 hours the reaction was poured into water to drop crystals and filtered. The filtered solid was completely dissolved in ethyl acetate, washed with water, and the resulting solution was concentrated under reduced pressure and purified by column chromatography. 86.90 g (yield 83%) of Formula 1A were obtained. [M] = 275
또한, 본 명세서는 상기 전술한 화합물을 포함하는 유기 전계 발광 소자를 제공한다. In addition, the present specification provides an organic electroluminescent device comprising the compound described above.
본 출원의 일 실시상태에 있어서, 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 유기물층 중 1 층 이상은 상기 헤테로고리 화합물을 포함하는 것인 유기 전계 발광 소자를 제공한다. In one embodiment of the present application, the first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the heterocyclic compound. .
본 명세서에서 어떤 부재가 다른 부재 "상에" 위치하고 있다고 할 때, 이는 어떤 부재가 다른 부재에 접해 있는 경우뿐 아니라 두 부재 사이에 또 다른 부재가 존재하는 경우도 포함한다.In this specification, when a member is located "on" another member, this includes not only when a member is in contact with another member but also when another member exists between the two members.
본 명세서에서 어떤 부분이 어떤 구성요소를 "포함" 한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성 요소를 더 포함할 수 있는 것을 의미한다. In the present specification, when a part "contains" a certain component, this means that the component may further include other components, except for the case where there is no contrary description.
본 출원의 유기 전계 발광 소자의 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 발명의 유기 전계 발광 소자의 대표 적인 예로서, 유기 전계 발광 소자는 유기물층으로서 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등을 포함하는 구조를 가질 수 있다. 그러나 유기 전계 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기층을 포함할 수 있다.The organic material layer of the organic electroluminescent device of the present application may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked. For example, as a representative example of the organic EL device of the present invention, the organic EL device may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic material layer. However, the structure of the organic electroluminescent device is not limited thereto and may include a smaller number of organic layers.
본 출원의 일 실시상태에 있어서, 상기 유기물층의 두께는 1Å 내지 1000Å이다.In an exemplary embodiment of the present application, the thickness of the organic material layer is 1 kPa to 1000 kPa.
본 출원의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 헤테로고리 화합물을 포함한다. In an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound.
본 출원의 일 실시상태에 있어서, 상기 유기물층은 정공주입층 또는 정공수송층을 포함하고, 상기 정공주입층 또는 정공수송층은 상기 헤테로고리 화합물을 포함한다. In an exemplary embodiment of the present application, the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the heterocyclic compound.
본 출원의 일 실시상태에 있어서, 상기 유기물층은 전자수송층 또는 전자주입층을 포함하고, 상기 전자수송층 또는 전자주입층은 상기 헤테로고리 화합물을 포함한다. In an exemplary embodiment of the present application, the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the heterocyclic compound.
본 출원의 일 실시상태에 있어서, 상기 유기물층은 전자저지층 또는 정공저지층을 포함하고, 상기 전자저지층 또는 정공저지층은 상기 헤테로고리 화합물을 포함한다. In an exemplary embodiment of the present application, the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer includes the heterocyclic compound.
본 출원의 일 실시상태에 있어서, 상기 유기물층은 전자저지층을 포함하고, 상기 전자저지층은 상기 헤테로고리 화합물을 포함한다.In an exemplary embodiment of the present application, the organic material layer includes an electron blocking layer, and the electron blocking layer includes the heterocyclic compound.
본 출원의 일 실시상태에 있어서, 상기 유기 전계 발광 소자는 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 발광층; 상기 발광층과 상기 제1 전극 사이, 또는 상기 발광층과 상기 제2 전극 사이에 구비된 2층 이상의 유기물층을 포함하고, 상기 2층 이상의 유기물층 중 적어도 하나는 상기 헤테로고리 화합물을 포함한다. In one embodiment of the present application, the organic electroluminescent device comprises a first electrode; A second electrode provided to face the first electrode; And a light emitting layer provided between the first electrode and the second electrode. Two or more organic material layers provided between the light emitting layer and the first electrode, or between the light emitting layer and the second electrode, wherein at least one of the two or more organic material layers includes the heterocyclic compound.
본 출원의 일 실시상태에 있어서, 상기 2층 이상의 유기물층은 전자수송층, 전자주입층, 전자 수송과 전자주입을 동시에 하는 층 및 정공저지층으로 이루어진 군에서 2 이상이 선택될 수 있다.In an exemplary embodiment of the present application, the two or more organic material layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer simultaneously performing electron transport and electron injection, and a hole blocking layer.
본 출원의 일 실시상태에 있어서, 상기 유기물층은 2층 이상의 전자수송층을 포함하고, 상기 2층 이상의 전자수송층 중 적어도 하나는 상기 헤테로고리 화합물을 포함한다. 구체적으로 본 명세서의 일 실시상태에 있어서, 상기 헤테로고리 화합물은 상기 2층 이상의 전자수송층 중 1층에 포함될 수도 있으며, 각각의 2층 이상의 전자수송층에 포함될 수 있다. In an exemplary embodiment of the present application, the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the heterocyclic compound. Specifically, in one embodiment of the present specification, the heterocyclic compound may be included in one layer of the two or more electron transport layers, and may be included in each of the two or more electron transport layers.
또한, 본 출원의 일 실시상태에 있어서, 상기 헤테로고리 화합물이 상기 각각의 2층 이상의 전자수송층에 포함되는 경우, 상기 헤테로고리 화합물을 제외한 다른 재료들은 서로 동일하거나 상이할 수 있다.In addition, in the exemplary embodiment of the present application, when the heterocyclic compound is included in each of the two or more electron transport layers, other materials except for the heterocyclic compound may be the same or different from each other.
본 출원의 일 실시상태에 있어서, 상기 유기물층은 상기 헤테로고리 화합물을 포함하는 유기물층 이외에 아릴아미노기, 카바졸릴기 또는 벤조카바졸릴기를 포함하는 화합물을 포함하는 정공주입층 또는 정공수송층을 더 포함한다. In an exemplary embodiment of the present application, the organic layer further includes a hole injection layer or a hole transport layer including a compound including an arylamino group, carbazolyl group or benzocarbazolyl group in addition to the organic layer including the heterocyclic compound.
또 하나의 실시상태에 있어서, 유기 전계 발광 소자는 기판 상에 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층된 구조(normal type)의 유기 전계 발광 소자일 수 있다. In another exemplary embodiment, the organic electroluminescent device may be an organic electroluminescent device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
또 하나의 실시상태에 있어서, 유기 전계 발광 소자는 기판 상에 음극, 1층 이상의 유기물층 및 양극이 순차적으로 적층된 역방향 구조(inverted type)의 유기 전계 발광 소자일 수 있다. In another exemplary embodiment, the organic electroluminescent device may be an organic electroluminescent device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
예컨대, 본 출원의 일 실시상태에 따른 유기 전계 발광 소자의 구조는 도 1 및 2에 예시되어 있다. For example, the structure of an organic EL device according to one embodiment of the present application is illustrated in FIGS. 1 and 2.
도 1은 기판(1), 양극(2), 발광층(3), 음극(4)이 순차적으로 적층된 유기 전계 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 헤테로고리 화합물은 상기 발광층(3)에 포함될 수 있다. 1 illustrates a structure of an organic EL device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked. In such a structure, the heterocyclic compound may be included in the light emitting layer (3).
도 2는 기판 (1), 양극(2), 정공주입층(5), 정공수송층(6), 발광층(3), 전자수송층(7) 및 음극(4)이 순차적으로 적층된 유기 전계 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서 상기 헤테로고리 화합물은 상기 정공주입층(5), 정공 수송층(6), 발광층(3) 및 전자 수송층(7) 중 1층 이상에 포함될 수 있다. 2 illustrates an organic electroluminescent device in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7 and a cathode 4 are sequentially stacked. The structure of is illustrated. In such a structure, the heterocyclic compound may be included in one or more layers of the hole injection layer 5, the hole transport layer 6, the light emitting layer 3, and the electron transport layer 7.
이와 같은 구조에 있어서, 상기 헤테로고리 화합물은 상기 정공주입층, 정공수송층, 발광층 및 전자수송층 중 1층 이상에 포함될 수 있다. In such a structure, the heterocyclic compound may be included in one or more layers of the hole injection layer, the hole transport layer, the light emitting layer and the electron transport layer.
본 출원의 유기 전계 발광 소자는 유기물층 중 1층 이상이 본 출원의 화합물, 즉 상기 헤테로고리 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다.The organic electroluminescent device of the present application may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of the present application, that is, the heterocyclic compound.
상기 유기 전계 발광 소자가 복수개의 유기물층을 포함하는 경우, 상기 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다. When the organic electroluminescent device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
본 출원의 유기 전계 발광 소자는 유기물층 중 1층 이상이 상기 헤테로고리 화합물, 즉 상기 화학식 1로 표시되는 헤테로고리 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다. The organic electroluminescent device of the present application may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the heterocyclic compound, that is, the heterocyclic compound represented by Formula 1 above. .
예컨대, 본 출원의 유기 전계 발광 소자는 기판 상에 제1 전극, 유기물층 및 제2 전극을 순차적으로 적층시킴으로써 제조할 수 있다. 이 때 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 유기물층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물층, 양극 물질을 차례로 증착시켜 유기 전계 발광 소자를 만들 수 있다. For example, the organic EL device of the present application may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode. And 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 the above method, an organic EL device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
또한, 상기 화학식 1의 화합물은 유기 전계 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.In addition, the compound of Formula 1 may be formed of an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic EL device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
이와 같은 방법 외에도, 기판 상에 음극 물질로부터 유기물층, 양극 물질을 차례로 증착시켜 유기 전계 발광 소자를 만들 수도 있다 (국제 특허 출원 공개 제 2003/012890호). 다만, 제조 방법이 이에 한정되는 것은 아니다. In addition to such a method, an organic electroluminescent device may be fabricated by sequentially depositing an organic material layer and an anode material on a substrate (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.
본 출원의 일 실시상태에 있어서, 상기 제1 전극은 양극이고, 상기 제2 전극은 음극이다. In one embodiment of the present application, the first electrode is an anode, and the second electrode is a cathode.
또 하나의 실시상태에 있어서, 상기 제1 전극은 음극이고, 상기 제2 전극은 양극이다. In another exemplary embodiment, the first electrode is a cathode and the second electrode is an anode.
상기 양극 물질로는 통상 유기물층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 본 발명에서 사용될 수 있는 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. As the anode material, a material having a large work function is usually preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material that can be used in the present invention 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), indium zinc oxide (IZO); ZnO: Al or SnO 2 : Combination of metals and oxides such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 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. It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material 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; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
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 유기물층의 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 for injecting holes from an electrode, and the hole injection material has a capability of transporting holes, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is generated in a light emitting layer The compound which prevents the movement of the excited excitons to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
상기 정공수송층은 정공주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로, 정공 수송 물질로는 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. As a hole transport material, the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer. The material is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
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 예로는 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 region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
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 화합물, 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이에 한정되지 않는다. The light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a heterocyclic containing compound. Specifically, the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and the heterocyclic containing compounds include compounds, dibenzofuran derivatives and ladder type furan compounds. , Pyrimidine derivatives, and the like, but is not limited thereto.
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 Al착물; 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 transporting material is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. The electron transporting material is a material that can inject electrons well from the cathode and move them to the light emitting layer. This is suitable. Specific examples thereof include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.
상기 전자주입층은 전극으로부터 전자를 주입하는 층으로, 전자를 수송하는 능력을 갖고, 음극으로부터의 전자주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며, 발광층에서 생성된 여기자의 정공 주입층에의 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 함질소 5원환 유도체 등이 있으나, 이에 한정되지 않는다. The electron injection layer is a layer that injects electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer. The compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
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 compound 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, It is not limited to this.
상기 정공저지층은 정공의 음극 도달을 저지하는 층으로, 일반적으로 정공주입층과 동일한 조건으로 형성될 수 있다. 구체적으로 옥사디아졸 유도체나 트리아졸 유도체, 페난트롤린 유도체, BCP, 알루미늄 착물 (aluminum complex) 등이 있으나, 이에 한정되지 않는다. The hole blocking layer is a layer for blocking the arrival of the cathode of the hole, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are not limited thereto.
이하, 본 명세서를 구체적으로 설명하기 위해 실시예를 들어 상세하게 설명하기로 한다. 그러나, 본 명세서에 따른 실시예들은 여러 가지 다른 형태로 변형될 수 있으며, 본 출원의 범위가 아래에서 상술하는 실시예들에 한정되는 것으로 해석되지 않는다. 본 출원의 실시예들은 당업계에서 평균적인 지식을 가진 자에게 본 명세서를 보다 완전하게 설명하기 위해 제공되는 것이다.Hereinafter, the present invention will be described in detail with reference to Examples. However, embodiments according to the present disclosure may be modified in various other forms, and the scope of the present application is not interpreted to be limited to the embodiments described below. Embodiments of the present application are provided to more fully describe the present specification to those skilled in the art.
합성예 1. 화합물 1Synthesis Example 1 Compound 1
화학식 1A 10.0 g (1.0 eq), N-(4-(9,9-디메틸-9H-플루오렌-2-일)페닐)비페닐-4-아민 14.44 g (1.1 eq), NaOtBu 6.98 g (2.0 eq), Pd(t-Bu3P)2 0.09 g (0.005 eq) 를 자일렌(Xylene) 90 ml 에 녹여 환류하여 교반했다. 1 시간 후 반응이 종료되면 감압하여 용매를 제거했다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거했다. 다시 환류 상태에서 에틸 아세테이트 를 넣어주며 결정을 떨어트려 식힌 후 여과했다. 이를 컬럼크로마토그래피하여 화합물 1을 17.24 g (수율 79 %) 얻었다. [M+H]=67710.0 g (1.0 eq) of Formula 1A, 14.44 g (1.1 eq) of N- (4- (9,9-dimethyl-9H-fluoren-2-yl) phenyl) biphenyl-4-amine, 6.98 g (2.0) of NaOtBu eq) and Pd (t-Bu 3 P) 2 0.09 g (0.005 eq) were dissolved in 90 ml of xylene, refluxed and stirred. After the reaction was completed after 1 hour, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl 3 , washed with water, and removed under reduced pressure by about 50%. At reflux, ethyl acetate was added and the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain 17.24 g (yield 79%) of compound 1. [M + H] = 677
합성예 2. 화합물 2Synthesis Example 2 Compound 2
화학식 1A 10.0 g (1.0 eq), N-(비페닐-4-일)-9,9-디메틸-9H-플루오렌-3-아민 17.48 g (1.1 eq), NaOtBu 6.98 g (2.0 eq), Pd(t-Bu3P)2 0.09 g (0.005 eq) 를 자일렌(Xylene) 90 ml 에 녹여 환류하여 교반했다. 1 시간 후 반응이 종료되면 감압하여 용매를 제거했다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거했다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과했다. 이를 컬럼크로마토그래피하여 화합물 2를 19.91 g (수율 81 %) 얻었다. [M]=600Formula 1A 10.0 g (1.0 eq), N- (biphenyl-4-yl) -9,9-dimethyl-9H-fluoren-3-amine 17.48 g (1.1 eq), NaOtBu 6.98 g (2.0 eq), Pd 0.09 g (0.005 eq) of (t-Bu 3 P) 2 was dissolved in 90 ml of xylene, refluxed and stirred. After the reaction was completed after 1 hour, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl 3 , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 19.91 g (yield 81%) of compound 2. [M] = 600
합성예 3. 화합물 3Synthesis Example 3 Compound 3
화학식 1A 10.0 g (1.0 eq), N-(4-(디벤조[b,d]퓨란-4-일)페닐)비페닐-4-아민 14.44 g (1.1 eq), NaOtBu 6.98 g (2.0 eq), Pd(t-Bu3P)2 0.09 g (0.005 eq) 를 자일렌(Xylene) 90 ml 에 녹여 환류하여 교반했다. 1 시간 후 반응이 종료되면 감압하여 용매를 제거했다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거했다. 다시 환류 상태에서 에틸 아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과했다. 이를 컬럼크로마토그래피하여 화합물 3을 16.80 g (수율 77 %) 얻었다. [M+H]=65110.0 g (1.0 eq), N- (4- (dibenzo [b, d] furan-4-yl) phenyl) biphenyl-4-amine 14.44 g (1.1 eq), 6.98 g (2.0 eq) NaOtBu 0.09 g (0.005 eq) of Pd (t-Bu 3 P) 2 was dissolved in 90 ml of xylene and refluxed to stir. After the reaction was completed after 1 hour, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl 3 , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 16.80 g (77% yield) of compound 3. [M + H] = 651
합성예 4. 화합물 4Synthesis Example 4 Compound 4
화학식 1A 10.0 g (1.0 eq), N-(4-(디벤조[b,d]티오펜-3-일)페닐)비페닐-4-아민 16.44 g (1.1 eq), NaOtBu 6.98 g (2.0 eq), Pd(t-Bu3P)2 0.09 g (0.005 eq) 를 자일렌(Xylene) 90 ml 에 녹여 환류하여 교반했다. 1 시간 후 반응이 종료되면 감압하여 용매를 제거했다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거했다. 다시 환류 상태에서 에틸 아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과했다. 이를 컬럼크로마토그래피하여 화합물 4를 19.62 g (수율 83 %) 얻었다. [M]=66610.0 g (1.0 eq), N- (4- (dibenzo [b, d] thiophen-3-yl) phenyl) biphenyl-4-amine 16.44 g (1.1 eq), 6.98 g (2.0 eq) NaOtBu ) And 0.09 g (0.005 eq) of Pd (t-Bu 3 P) 2 were dissolved in 90 ml of xylene and refluxed to stir. After the reaction was completed after 1 hour, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl 3 , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 19.62 g (yield 83%) of compound 4. [M] = 666
합성예 5. 화합물 5Synthesis Example 5 Compound 5
화학식 1A 10.0 g (1.0 eq), 4-(비페닐-4-일(4-(디벤조[b,d]thiophen-4-일)페닐)아미노)페닐 보론산21.88 g (1.1 eq), 물 40ml 에 녹인K3PO4 15.43 g (2.0 eq), Pd(t-Bu3P)2 0.09 g (0.005 eq) 를 디옥산 90 ml 에 녹여 환류하여 교반했다. 1 시간 후 반응이 종료되면 감압하여 용매를 제거했다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거했다. 다시 환류 상태에서 에틸 아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과했다. 이를 컬럼크로마토그래피하여 화합물 5를 21.85 g (수율 81 %) 얻었다. [M+H]=74310.0 g (1.0 eq) of formula 1A, 4- (biphenyl-4-yl (4- (dibenzo [b, d] thiophen-4-yl) phenyl) amino) phenyl boronic acid21.88 g (1.1 eq), water 15.43 g (2.0 eq) of K 3 PO 4 dissolved in 40 ml and 0.09 g (0.005 eq) of Pd (t-Bu 3 P) 2 were dissolved in 90 ml of dioxane and refluxed to stir. After the reaction was completed after 1 hour, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl 3 , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 21.85 g (yield 81%) of compound 5. [M + H] = 743
합성예 6. 화합물 6Synthesis Example 6 Compound 6
화학식 1A 10.0 g (1.0 eq), 4-(비페닐-4-일(4-(9,9-디메틸-9H-플루오렌-2-일)페닐)아미노)페닐 보론산 22.28 g (1.1 eq), 물 40ml 에 녹인K3PO4 15.43 g (2.0 eq), Pd(t-Bu3P)2 0.09 g (0.005 eq) 를 디옥산 90 ml 에 녹여 환류하여 교반했다. 1 시간 후 반응이 종료되면 감압하여 용매를 제거했다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거했다. 다시 환류 상태에서 에틸 아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과했다. 이를 컬럼크로마토그래피하여 화합물 6을 23.24 g (수율 85 %) 얻었다. [M]=75210.0 g (1.0 eq) of Formula 1A, 4- (biphenyl-4-yl (4- (9,9-dimethyl-9H-fluoren-2-yl) phenyl) amino) phenyl boronic acid 22.28 g (1.1 eq) 15.43 g (2.0 eq) of K 3 PO 4 and 0.09 g (0.005 eq) of Pd (t-Bu 3 P) 2 dissolved in 40 ml of water were dissolved in 90 ml of dioxane and refluxed to stir. After the reaction was completed after 1 hour, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl 3 , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 23.24 g (yield 85%) of compound 6. [M] = 752
합성예 7. 화합물 7Synthesis Example 7 Compound 7
화학식 1A 10.0 g (1.0 eq), 4-((4-(9,9-디메틸-9H-플루오렌-2-일)페닐)(트리페닐렌-2-일)아미노)페닐 보론산25.24 g (1.1 eq), 물 40ml 에 녹인K3PO4 15.43 g (2.0 eq), Pd(t-Bu3P)2 0.09 g (0.005 eq) 를 디옥산90 ml 에 녹여 환류하여 교반했다. 1 시간 후 반응이 종료되면 감압하여 용매를 제거했다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거했다. 다시 환류 상태에서 Ethyl acetate 를 넣어주며 결정을 떨어트려 식힌 후 여과했다. 이를 컬럼크로마토그래피하여 화합물 7을 25.83 g (수율 86 %) 얻었다. [M]=82610.0 g (1.0 eq) of formula 1A, 4-((4- (9,9-dimethyl-9H-fluoren-2-yl) phenyl) (triphenylen-2-yl) amino) phenyl boronic acid25.24 g ( 1.1 eq), 15.43 g (2.0 eq) of K 3 PO 4 dissolved in 40 ml of water, and 0.09 g (0.005 eq) of Pd (t-Bu 3 P) 2 were dissolved in 90 ml of dioxane and refluxed and stirred. After the reaction was completed after 1 hour, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl 3 , washed with water, and removed under reduced pressure by about 50%. At reflux, Ethyl acetate was added and the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain 25.83 g (yield 86%) of compound 7. [M] = 826
합성예 8. 화합물 8Synthesis Example 8 Compound 8
화학식 1A10.0 g (1.0 eq), 4-((4-(디벤조[b,d]티오펜-4-일)페닐)(트리페닐렌-2-일)아미노)페닐 보론산 24.84 g (1.1 eq), 물 40ml 에 녹인K3PO4 15.43 g (2.0 eq), Pd(t-Bu3P)2 0.09 g (0.005 eq) 를 디옥산90 ml 에 녹여 환류하여 교반했다. 1 시간 후 반응이 종료되면 감압하여 용매를 제거했다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거했다. 다시 환류 상태에서 에틸 아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과했다. 이를 컬럼크로마토그래피하여 화합물 8을 24.63 g (수율 83 %) 얻었다. [M+H]=81710.0 g (1.0 eq), 4-((4- (dibenzo [b, d] thiophen-4-yl) phenyl) (triphenylen-2-yl) amino) phenyl boronic acid 24.84 g ( 1.1 eq), 15.43 g (2.0 eq) of K 3 PO 4 dissolved in 40 ml of water, and 0.09 g (0.005 eq) of Pd (t-Bu 3 P) 2 were dissolved in 90 ml of dioxane and refluxed and stirred. After the reaction was completed after 1 hour, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl 3 , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 24.63 g (yield 83%) of compound 8. [M + H] = 817
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비교예Comparative example
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ITO(indium tin oxide)가 1,000Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이 때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀러포어사(Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 수송시켰다. 이렇게 준비된 ITO 투명 전극 위에 하기 화학식의 헥사니트릴 헥사아자트리페닐렌 (hexaazatriphenylene; HAT-CN)를 150Å의 두께로 열 진공 증착하여 정공 주입층을 형성하였다. 상기 정공 주입층 위에 정공을 수송하는 물질인 하기 화합물 HT(1150Å)를 진공 증착하여 정공 수송층을 형성하였다. 이어서, 상기 정공 수송층 위에 막 두께 150Å으로 하기 화합물 EB를 진공 증착하여 전자 저지층을 형성하였다. 이어서, 상기 전자 저지층 위에 막 두께 30Å으로 아래와 같은 BH와 BD를 25:1의 중량비로 진공증착하여 발광층을 형성하였다. 상기 발광층 위에 상기 화합물 ET과 상기 화합물 LiQ(Lithium Quinolate)를 1:1의 중량비로 진공증착하여 360Å의 두께로 전자 주입 및 수송층을 형성하였다. 상기 전자 주입 및 수송층 위에 순차적으로 12Å두께로 리튬플로라이드(LiF)와 2,000Å 두께로 알루미늄을 증착하여 음극을 형성하였다. 상기의 과정에서 유기물의 증착속도는 0.4~ 0.7Å/sec를 유지하였고, 음극의 리튬플로라이드는 0.3Å/sec, 알루미늄은 2Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 2 ×10-7 ~5 ×10-6 torr를 유지하여, 유기 전계 발광 소자를 제작하였다.A glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and ultrasonically cleaned. At this time, Fischer Co. product was used as a detergent, and distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water. After ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After washing the distilled water, ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator. The hexanitrile hexaazatriphenylene (HAT-CN) of the following formula was thermally vacuum deposited to a thickness of 150 kPa on the prepared ITO transparent electrode to form a hole injection layer. Compound HT (1150 kV), which is a material for transporting holes, was vacuum deposited on the hole injection layer to form a hole transport layer. Subsequently, the following compound EB was vacuum deposited on the hole transport layer with a film thickness of 150 GPa to form an electron blocking layer. Subsequently, BH and BD as described below were vacuum-deposited at a weight ratio of 25: 1 on the electron blocking layer to form a light emitting layer. Compound ET and the compound LiQ (Lithium Quinolate) were vacuum-deposited on the emission layer in a weight ratio of 1: 1 to form an electron injection and transport layer with a thickness of 360 Pa. On the electron injection and transport layer, lithium fluoride (LiF) and aluminum were deposited to a thickness of 12 kPa in order to form a cathode. Was maintained at the deposition rate was 0.4 ~ 0.7Å / sec for organic material in the above process, the lithium fluoride of the cathode was 0.3Å / sec, aluminum is deposited at a rate of 2Å / sec, During the deposition, a vacuum 2 × 10 - The organic electroluminescent element was produced, maintaining 7-5 * 10 <-6> torr.
<실험예 1-1><Experimental Example 1-1>
상기 비교예에서 화합물 EB 대신 상기 화합물 1을 사용한 것을 제외하고는 비교예와 동일한 방법으로 유기 전계 발광 소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Comparative Example, except that Compound 1 was used instead of Compound EB in the Comparative Example.
<실험예 1-2><Experimental Example 1-2>
상기 비교예에서 화합물 EB 대신 상기 화합물 2를 사용한 것을 제외하고는 비교예와 동일한 방법으로 유기 전계 발광 소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Comparative Example, except that Compound 2 was used instead of Compound EB in the Comparative Example.
<실험예 1-3><Experimental Example 1-3>
상기 비교예에서 화합물 EB 대신 상기 화합물 3을 사용한 것을 제외하고는 비교예와 동일한 방법으로 유기 전계 발광 소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Comparative Example, except that Compound 3 was used instead of Compound EB in the Comparative Example.
<실험예 1-4><Experimental Example 1-4>
상기 비교예에서 화합물 EB 대신 상기 화합물 4를 사용한 것을 제외하고는 비교예와 동일한 방법으로 유기 전계 발광 소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Comparative Example, except that Compound 4 was used instead of Compound EB in the Comparative Example.
<실험예 1-5><Experimental Example 1-5>
상기 비교예에서 화합물 EB 대신 상기 화합물 5를 사용한 것을 제외하고는 비교예와 동일한 방법으로 유기 전계 발광 소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Comparative Example, except that Compound 5 was used instead of Compound EB in the Comparative Example.
<실험예 1-6><Experimental Example 1-6>
상기 비교예에서 화합물 EB 대신 상기 화합물 6을 사용한 것을 제외하고는 비교예와 동일한 방법으로 유기 전계 발광 소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Comparative Example, except that Compound 6 was used instead of Compound EB in the Comparative Example.
<실험예 1-7><Experimental Example 1-7>
상기 비교예에서 화합물 EB 대신 상기 화합물 7을 사용한 것을 제외하고는 비교예와 동일한 방법으로 유기 전계 발광 소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Comparative Example, except that Compound 7 was used instead of Compound EB in the Comparative Example.
<실험예 1-8><Experimental Example 1-8>
상기 비교예에서 화합물 EB 대신 상기 화합물 8을 사용한 것을 제외하고는 비교예와 동일한 방법으로 유기 전계 발광 소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Comparative Example, except that Compound 8 was used instead of Compound EB in the Comparative Example.
<비교예 1>Comparative Example 1
상기 비교예에서 화합물 EB 대신 상기 H-1의 화합물을 사용한 것을 제외하고는 상기 비교예와 동일한 방법으로 유기 전계 발광 소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Comparative Example, except that the compound of H-1 was used instead of the compound EB in the comparative example.
<비교예 2>Comparative Example 2
상기 비교예에서 화합물 EB 대신 상기 H-2의 화합물을 사용한 것을 제외하고는 상기 비교예와 동일한 방법으로 유기 전계 발광 소자를 제작하였다.An organic light emitting diode was manufactured according to the same method as the comparative example except for using the compound of H-2 instead of compound EB in the comparative example.
<비교예 3>Comparative Example 3
상기 비교예에서 화합물 EB 대신 상기 H-3의 화합물을 사용한 것을 제외하고는 상기 비교예와 동일한 방법으로 유기 전계 발광 소자를 제작하였다.An organic electroluminescent device was manufactured according to the same method as the comparative example except for using the compound of H-3 instead of the compound EB in the comparative example.
<비교예 4><Comparative Example 4>
상기 비교예에서 화합물 EB 대신 상기 H-4의 화합물을 사용한 것을 제외하고는 상기 비교예와 동일한 방법으로 유기 전계 발광 소자를 제작하였다.An organic light emitting device was manufactured according to the same method as the comparative example except for using the compound of H-4 instead of compound EB in the comparative example.
<비교예 5>Comparative Example 5
상기 비교예에서 화합물 EB 대신 상기 H-5의 화합물을 사용한 것을 제외하고는 상기 비교예와 동일한 방법으로 유기 전계 발광 소자를 제작하였다.An organic light emitting diode was manufactured according to the same method as the comparative example except for using the compound of H-5 instead of the compound EB in the comparative example.
<비교예 6>Comparative Example 6
상기 비교예에서 화합물 EB 대신 상기 H-6의 화합물을 사용한 것을 제외하고는 상기 비교예와 동일한 방법으로 유기 전계 발광 소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Comparative Example, except that the compound of H-6 was used instead of the compound EB in the comparative example.
실험예 1-1 내지 1-8 및 비교예 1 내지 6 에 의해 제작된 유기 발광 소자에 전류를 인가하였을 때, 전압, 전류밀도, 휘도, 색좌표 및 수명을 측정하고 그 결과를 하기 [표 1]에 나타내었다. T95은 휘도가 초기휘도(650nit)에서 95%로 감소되는데 소요되는 시간을 의미한다.When current was applied to the organic light emitting devices manufactured by Experimental Examples 1-1 to 1-8 and Comparative Examples 1 to 6, voltage, current density, brightness, color coordinate, and lifetime were measured, and the results are shown in the following [Table 1]. Shown in T95 means the time taken for the luminance to decrease to 95% from the initial luminance (650 nits).
| 전자저지층Electronic floor | 전압 V(@10mA/cm2)Voltage V (@ 10mA / cm 2 ) | 효율 cd/A(@10mA/cm2)Efficiency cd / A (@ 10mA / cm 2 ) | 발광색Luminous color | T95T95 | |
| 실험예 1-1Experimental Example 1-1 |
화합물 1 |
3.833.83 | 5.305.30 | 청 색blue | 205205 |
| 실험예 1-2Experimental Example 1-2 |
화합물 2 |
3.853.85 | 5.275.27 | 청 색blue | 200200 |
| 실험예 1-3Experimental Example 1-3 |
화합물 3 |
3.803.80 | 5.355.35 | 청 색blue | 215215 |
| 실험예 1-4Experimental Example 1-4 |
화합물 4 |
3.823.82 | 5.325.32 | 청 색blue | 210210 |
| 실험예 1-5Experimental Example 1-5 |
화합물 5 |
3.743.74 | 5.415.41 | 청 색blue | 240240 |
| 실험예 1-6Experimental Example 1-6 |
화합물 6 |
3.763.76 | 5.395.39 | 청 색blue | 234234 |
| 실험예 1-7Experimental Example 1-7 |
화합물 7 |
3.703.70 | 5.465.46 | 청 색blue | 225225 |
| 실험예 1-8Experimental Example 1-8 |
화합물 8 |
3.683.68 | 5.485.48 | 청 색blue | 230230 |
| 비교예 1Comparative Example 1 | H-1H-1 | 4.184.18 | 4.874.87 | 청 색blue | 163163 |
| 비교예 2Comparative Example 2 | H-2H-2 | 4.134.13 | 4.914.91 | 청 색blue | 166166 |
| 비교예 3Comparative Example 3 | H-3H-3 | 4.254.25 | 4.704.70 | 청 색blue | 170170 |
| 비교예 4Comparative Example 4 | H-4H-4 | 4.224.22 | 4.794.79 | 청 색blue | 177177 |
| 비교예 5Comparative Example 5 | H-5H-5 | 4.054.05 | 5.025.02 | 청 색blue | 186186 |
| 비교예 6Comparative Example 6 | H-6H-6 | 4.094.09 | 4.974.97 | 청 색blue | 183183 |
상기 표 1에서 보는 바와 같이, 본원 발명의 화합물을 전자 저지층으로 사용하여 제조된 유기 전계 발광 소자의 경우에 유기 전계 발광 소자의 효율, 구동전압 및/또는 안정성 면에서 우수한 특성을 나타낸다.As shown in Table 1, the organic electroluminescent device manufactured by using the compound of the present invention as an electron blocking layer exhibits excellent characteristics in terms of efficiency, driving voltage and / or stability of the organic electroluminescent device.
본원발명의 코어는 비교예 1 내지 6 의 화합물을 전자 저지층으로 사용하여 제조된 유기 발광 소자보다 저전압, 고효율 및 장수명의 특성을 보인다. 전압은 5~10%정도 낮아지며 효율은 10%이상 높아졌다. 기존의 인돌로[3,2,1-jk]카바졸의 2번, 10번, 11번에 연결된 아민의 방향을 본 발명의 화합물 처럼 입체장애가 많은 방향(1번)으로 연결 하고 컨쥬게이션이 끊어지는 방향으로 연결시 효율 상승, 전압 감소, 장수명의 특성을 보이는 것으로 코어 인돌로[3,2,1-jk]카바졸 자체의 안정성도 높아진다는 것을 알 수 있었다. 또한 코어와 아민이 연결된 부분이 많이 꺾여 있기에 열 안정성에 있어도 우수한 장점을 갖고 있다. The core of the present invention exhibits lower voltage, higher efficiency and longer life than organic light emitting devices manufactured by using the compounds of Comparative Examples 1 to 6 as the electron blocking layer. Voltage is reduced by 5-10% and efficiency is increased by more than 10%. The amines connected to Nos. 2, 10, and 11 of the existing indolo [3,2,1-jk] carbazole are connected in the steric hindrance as the compound of the present invention (No. 1) and the conjugation is broken. It showed that the stability of the core indolo [3,2,1-jk] carbazole itself was increased by showing the efficiency increase, the voltage decrease and the long life when connected in the losing direction. In addition, since the portion where the core and the amine are connected to each other is bent, it has excellent advantages in thermal stability.
Claims (12)
- 하기 화학식 1로 표시되는 헤테로고리 화합물:Heterocyclic compounds represented by the formula (1):[화학식 1][Formula 1]
상기 화학식 1에 있어서, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,In Formula 1, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,L1 내지 L3는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 2가의 헤테로고리기이며,L1 to L3 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,R1 내지 R3는 서로동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,a는 0 내지 2의 정수이고, b 및 c는 0 내지 4의 정수이며, a 내지 c가 2이상인 경우 괄호안의 치환기는 같거나 상이하다. a is an integer of 0 to 2, b and c are integers of 0 to 4, and when a to c are 2 or more, the substituents in parentheses are the same or different. - 청구항 1에 있어서, 상기 Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기인 것을 특징으로 하는 헤테로고리 화합물.The method of claim 1, wherein Ar1 and Ar2 are the same as or different from each other, each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
- 청구항 1에 있어서, 상기 Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 페닐기로 치환 또는 비치환된 페닐기; 페닐기로 치환 또는 비치환된 비페닐기; 페닐기로 치환 또는 비치환된 터페닐기; 페닐기로 치환 또는 비치환된 트리페닐렌기; 페닐기로 치환 또는 비치환된 디메틸플루오렌기; 페닐기로 치환 또는 비치환된 디벤조퓨란기; 페닐기로 치환 또는 비치환된 디벤조티오펜기; 또는 페닐기로 치환 또는 비치환된 카바졸기인 것인 헤테로고리 화합물.The method of claim 1, wherein Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a phenyl group; A biphenyl group unsubstituted or substituted with a phenyl group; Terphenyl group unsubstituted or substituted with a phenyl group; Triphenylene group unsubstituted or substituted with a phenyl group; Dimethyl fluorene group unsubstituted or substituted with a phenyl group; Dibenzofuran group unsubstituted or substituted with a phenyl group; Dibenzothiophene group unsubstituted or substituted with a phenyl group; Or a carbazole group unsubstituted or substituted with a phenyl group.
- 청구항 1에 있어서, 상기 L1은 직접결합; 페닐렌기; 2가의 디벤조퓨라닐기; 2가의 디벤조티오페닐기; 2가의 플루오레닐기; 또는 2가의 디메틸플루오레닐인 헤테로고리 화합물.The method according to claim 1, wherein L1 is a direct bond; Phenylene group; Divalent dibenzofuranyl group; Divalent dibenzothiophenyl group; Divalent fluorenyl group; Or heterocyclic dimethylfluorenyl.
- 청구항 1에 있어서, 상기 L2 및 L3 은 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 또는 페닐렌기인 것인 헤테로고리 화합물.The method of claim 1, wherein L2 and L3 are the same as or different from each other, and each independently a direct bond; Or a phenylene group.
- 청구항 1에 있어서, 상기 R1 내지 R3는 수소인 것인 헤테로고리 화합물.The heterocyclic compound of claim 1, wherein R 1 to R 3 are hydrogen.
- 청구항 1에 있어서, 상기 화학식 1의 화합물은 하기 구조식들에서 선택되는 것인 헤테로고리 화합물:The heterocyclic compound according to claim 1, wherein the compound of Formula 1 is selected from the following structural formulas:
- 제1 전극; 상기 제 1전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 유기물층 중 적어도 하나는 청구항 1 내지 7 중 어느 한 항에 따른 헤테로고리 화합물을 포함하는 것인 유기 전계 발광 소자.A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a heterocyclic compound according to any one of claims 1 to 7. Phosphorescent organic electroluminescent device.
- 청구항 8에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 헤테로고리 화합물을 포함하는 것인 유기 전계 발광 소자.The organic electroluminescent device according to claim 8, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound.
- 청구항 8에 있어서, 상기 유기물층은 정공주입층 또는 정공수송층을 포함하고, 상기 정공주입층 또는 정공수송층은 상기 헤테로고리 화합물을 포함하는 것인 유기 전계 발광 소자.The organic electroluminescent device according to claim 8, wherein the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the heterocyclic compound.
- 청구항 8에 있어서, 상기 유기물층은 전자수송층 또는 전자주입층을 포함하고, 상기 전자수송층 또는 전자주입층은 상기 헤테로고리 화합물을 포함 것인 유기 전계 발광 소자.The organic electroluminescent device according to claim 8, wherein the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the heterocyclic compound.
- 청구항 8에 있어서, 상기 유기물층은 전자 저지층을 포함하고, 상기 전자 저지층은 상기 헤테로고리 화합물을 포함하는 것인 유기 전계 발광 소자.The organic electroluminescent device according to claim 8, wherein the organic material layer includes an electron blocking layer, and the electron blocking layer includes the heterocyclic compound.
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