KR102573956B1 - Light-emitting material for organic electroluminescent device, organic electroluminescent device using same, and material for organic electroluminescent device - Google Patents
Light-emitting material for organic electroluminescent device, organic electroluminescent device using same, and material for organic electroluminescent device Download PDFInfo
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- KR102573956B1 KR102573956B1 KR1020220035274A KR20220035274A KR102573956B1 KR 102573956 B1 KR102573956 B1 KR 102573956B1 KR 1020220035274 A KR1020220035274 A KR 1020220035274A KR 20220035274 A KR20220035274 A KR 20220035274A KR 102573956 B1 KR102573956 B1 KR 102573956B1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LGLJXZWEUGZQRX-UHFFFAOYSA-N n,n-diphenyl-6-[4-(n-phenylanilino)phenyl]pyren-1-amine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C2=CC=C3C=CC(=C4C=CC(C2=C43)=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 LGLJXZWEUGZQRX-UHFFFAOYSA-N 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
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Abstract
발광 파장 조절 및 발광 효율이 우수한 말로노나이트릴(malononitrile) 화합물, 그의 제조방법 및 상기 말로노나이트릴(malononitrile) 화합물을 포함하는 유기전자소자를 제시한다.A malononitrile compound with excellent emission wavelength control and luminous efficiency, a manufacturing method thereof, and an organic electronic device including the malononitrile compound are provided.
Description
본 발명은 말로노나이트릴(malononitrile) 화합물, 이의 제조방법 및 이를 이용한 유기전자소자의 발전에 기여하고자 하는 기술에 관한 것이다.The present invention relates to a malononitrile compound, a manufacturing method thereof, and a technique intended to contribute to the development of an organic electronic device using the same.
일반적으로 유기발광 다이오드(OLED: Organic Light Emitting Diodes)는 음극, 양극 및 음극과 양극 사이에 개재된 유기물 층으로 구성되어 있다. 소자의 구성을 전체적으로 보면 투명 ITO 양극, 정공주입층(HIL), 정공전달층(HTL), 발광층(EL), 정공저지층(HBL), 전자전달층(ETL), 전자주입층(EIL) 및 LiAl 등의 음극으로 형성되며, 필요에 따라 유기물 층의 1~2 개를 생략하는 경우도 있다. 구성된 양 전극 사이에 전계가 인가되면 음극 측으로부터 전자가 주입되고 양극 측으로부터 정공이 주입된다. 또한, 이 전자가 발광층에 정공과 재결합하여 여기상태를 생성하고, 여기상태가 기저상태로 되돌아갈 때에 에너지를 빛으로서 방출한다. 이러한 발광 재료는 크게 형광과 인광으로 나뉘며, 발광층 형성방법은 형광 호스트(순수 유기물)에 인광(유기금속)을 도핑하는 방법과 형광 호스트에 형광 도판트(질소 등을 포함하는 유기물)를 도핑하는 방법 및 발광체에 도판트 (DCM, Rubrene, DCJTB 등)를 이용하여 장파장을 구현하는 방법 등이 있다. 이러한 도핑을 통해 발광 파장, 효율, 구동전압, 수명 등을 개선하려 하고 있다. 일반적으로 발광층 및 공동층 형성용 리간드 재료들은 벤젠, 나프탈렌, 플로렌, 스파이로플로렌, 안트라센, 파이렌, 카바졸 등의 중심체와 페닐, 바이페닐, 나프탈렌, 헤테로사이클 등의 리간드 그리고 오르소, 메타, 파라 등의 결합 위치 및 아민, 시안, 불소, 메틸, 트리메틸 등이 치환된 구조들을 갖는다.In general, organic light emitting diodes (OLEDs) are composed of a cathode, an anode, and an organic material layer interposed between the cathode and anode. Looking at the overall configuration of the device, the transparent ITO anode, hole injection layer (HIL), hole transport layer (HTL), light emitting layer (EL), hole blocking layer (HBL), electron transport layer (ETL), electron injection layer (EIL), and It is formed with a cathode such as LiAl, and if necessary, one or two organic layers may be omitted. When an electric field is applied between both electrodes, electrons are injected from the cathode side and holes are injected from the anode side. In addition, these electrons recombine with holes in the light emitting layer to generate an excited state, and when the excited state returns to the ground state, energy is emitted as light. These light-emitting materials are largely divided into fluorescence and phosphorescence, and the light-emitting layer formation method is a method of doping a phosphorescence (organic metal) into a fluorescence host (pure organic material) and a method of doping a fluorescence dopant (organic material containing nitrogen, etc.) into a fluorescent host. and a method of implementing a long wavelength by using a dopant (DCM, Rubrene, DCJTB, etc.) on a light emitting body. Through such doping, the emission wavelength, efficiency, driving voltage, and lifetime are being improved. In general, ligand materials for forming the light emitting layer and the common layer include a core such as benzene, naphthalene, florene, spiroflorene, anthracene, pyrene, and carbazole, ligands such as phenyl, biphenyl, naphthalene, and heterocycle, and ortho, meta , para, etc., and structures in which amine, cyan, fluorine, methyl, trimethyl, etc. are substituted.
현재 디스플레이의 화면이 대형화 방향으로 진행되면서 OLED의 경우 더 섬세하며, 더 선명한 색들의 재료들이 요구되고 있다. 또한 발광파장의 색 좌표 이외에, 소자의 낮은 구동전압에서 높은 발광효율 및 재료의 화학 구조적 열 안정성이 높은 유리전이온도 등을 요구한다. As the screen of the current display progresses in the direction of large-size, in the case of OLED, materials with more delicate and more vivid colors are required. In addition to the color coordinates of the emission wavelength, a high luminous efficiency at a low driving voltage of the device and a high glass transition temperature and chemical structural thermal stability of the material are required.
본 발명은 성능이 우수한 평면형 구조의 유기발광 소자의 성능 향상을 위한 말로노나이트릴(malononitrile) 화합물을 제공하는 것을 목적으로 한다. 본 발명은 말로노나이트릴(malononitrile) 화합물을 이용하여, 평면형 구조의 재료 개발을 통해 성능이 우수한 유기전기소자의 제공하는 것을 목적으로 한다. 본 발명은 말로노나이트릴(malononitrile) 화합물을 이용한 유기발광소자 재료 개발을 목적으로 한다.An object of the present invention is to provide a malononitrile compound for improving the performance of an organic light emitting device having a planar structure having excellent performance. An object of the present invention is to provide an organic electric device with excellent performance through the development of a material having a planar structure using a malononitrile compound. An object of the present invention is to develop an organic light emitting device material using a malononitrile compound.
본 발명은 하기 화학식 1-1에서 화학식 1-10 중 어느 하나로 표시되는 말로노나이트릴(malononitrile) 화합물:The present invention relates to a malononitrile compound represented by any one of Formulas 1-10 in Formula 1-1:
[화학식 1-1][Formula 1-1]
[화학식 1-2][Formula 1-2]
[화학식 1-3][Formula 1-3]
[화학식 1-4][Formula 1-4]
[화학식 1-5][Formula 1-5]
[화학식 1-6][Formula 1-6]
[화학식 1-7][Formula 1-7]
[화학식 1-8][Formula 1-8]
[화학식 1-9][Formula 1-9]
[화학식 1-10][Formula 1-10]
상기 R1 내지 R6은 각각 서로 독립적으로 수소; The R 1 to R 6 are each independently hydrogen;
치환 또는 비치환된 탄소수 1 내지 40개의 알킬기; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms;
치환 또는 비치환된 탄소수 2 내지 40개의 알킬알콕시기;A substituted or unsubstituted alkyl alkoxy group having 2 to 40 carbon atoms;
치환 또는 비치환된 탄소수 6 내지 40개의 아릴기; A substituted or unsubstituted aryl group having 6 to 40 carbon atoms;
치환 또는 비치환된 탄소수 7 내지 40개의 아릴알킬기; A substituted or unsubstituted arylalkyl group having 7 to 40 carbon atoms;
치환 또는 비치환된 탄소수 6 내지 40개의 아릴아민기; A substituted or unsubstituted arylamine group having 6 to 40 carbon atoms;
치환 또는 비치환된 탄소수 6 내지 30개의 시아노아릴기; A substituted or unsubstituted cyanoaryl group having 6 to 30 carbon atoms;
치환 또는 비치환된 탄소수 6 내지 30개의 플루오로아릴기; A substituted or unsubstituted fluoroaryl group having 6 to 30 carbon atoms;
치환 또는 비치환된 탄소수 11 내지 40개의 헤테로아릴기; A substituted or unsubstituted heteroaryl group having 11 to 40 carbon atoms;
치환 또는 비치환된 탄소수 6 내지 40개의 아미노아릴기; A substituted or unsubstituted aminoaryl group having 6 to 40 carbon atoms;
치환 또는 비치환된 탄소수 5 내지 40개의 아미노헤테로아릴기; A substituted or unsubstituted aminoheteroaryl group having 5 to 40 carbon atoms;
중에서 선택되고,is selected from
상기 Ar1은 The Ar 1 is
치환 또는 비치환된 탄소수 1 내지 40개의 알킬기; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms;
치환 또는 비치환된 탄소수 2 내지 40개의 알킬알콕시기;A substituted or unsubstituted alkyl alkoxy group having 2 to 40 carbon atoms;
치환 또는 비치환된 탄소수 6 내지 40개의 아릴기; A substituted or unsubstituted aryl group having 6 to 40 carbon atoms;
치환 또는 비치환된 탄소수 7 내지 40개의 아릴알킬기; A substituted or unsubstituted arylalkyl group having 7 to 40 carbon atoms;
치환 또는 비치환된 탄소수 6 내지 40개의 아릴아민기; A substituted or unsubstituted arylamine group having 6 to 40 carbon atoms;
치환 또는 비치환된 탄소수 6 내지 30개의 시아노아릴기; A substituted or unsubstituted cyanoaryl group having 6 to 30 carbon atoms;
치환 또는 비치환된 탄소수 6 내지 30개의 플루오로아릴기; A substituted or unsubstituted fluoroaryl group having 6 to 30 carbon atoms;
치환 또는 비치환된 탄소수 11 내지 40개의 헤테로아릴기; A substituted or unsubstituted heteroaryl group having 11 to 40 carbon atoms;
중에서 선택된다.are selected from
본 발명은 말로노나이트릴(malononitrile) 화합물을 이용한 유기 전자 소자를 제공한다.The present invention provides an organic electronic device using a malononitrile compound.
본 발명에 따르는 말로노나이트릴(malononitrile) 화합물은 대칭과 비대칭 및 평면형의 구조를 제공하며, 또한 본 발명의 대칭과 비대칭 및 평면형의 구조는 성능이 우수하며, 본 발명은 특정 구조의 말로노나이트릴(malononitrile) 화합물을 이용하여 유기발광 소자의 성능이 우수하다. The malononitrile compound according to the present invention provides a symmetric, asymmetric and planar structure, and the symmetric, asymmetric and planar structure of the present invention has excellent performance, and the present invention provides a specific structure of malononitrile. Performance of an organic light emitting device is excellent by using a malononitrile compound.
이하 본 발명을 보다 상세하게 설명한다. 하기의 구체적 설명은 본 발명의 일례를 들어 설명하는 것이므로 본 발명이 이에 한정되지 않는다.Hereinafter, the present invention will be described in more detail. The following specific description is for explaining an example of the present invention, so the present invention is not limited thereto.
본 발명의 일 측면에 따라, 하기 화학식 1-1에서 화학식 1-10 중 어느 하나로 표시되는 말로노나이트릴(malononitrile) 화합물:According to one aspect of the present invention, a malononitrile compound represented by any one of Formulas 1-10 in Formula 1-1:
[화학식 1-1][Formula 1-1]
[화학식 1-2][Formula 1-2]
[화학식 1-3][Formula 1-3]
[화학식 1-4][Formula 1-4]
[화학식 1-5][Formula 1-5]
[화학식 1-6][Formula 1-6]
[화학식 1-7][Formula 1-7]
[화학식 1-8][Formula 1-8]
[화학식 1-9][Formula 1-9]
[화학식 1-10][Formula 1-10]
상기 R1 내지 R6은 각각 서로 독립적으로 수소; The R 1 to R 6 are each independently hydrogen;
치환 또는 비치환된 탄소수 1 내지 40개의 알킬기; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms;
치환 또는 비치환된 탄소수 2 내지 40개의 알킬알콕시기;A substituted or unsubstituted alkyl alkoxy group having 2 to 40 carbon atoms;
치환 또는 비치환된 탄소수 6 내지 40개의 아릴기; A substituted or unsubstituted aryl group having 6 to 40 carbon atoms;
치환 또는 비치환된 탄소수 7 내지 40개의 아릴알킬기; A substituted or unsubstituted arylalkyl group having 7 to 40 carbon atoms;
치환 또는 비치환된 탄소수 6 내지 40개의 아릴아민기; A substituted or unsubstituted arylamine group having 6 to 40 carbon atoms;
치환 또는 비치환된 탄소수 6 내지 30개의 시아노아릴기; A substituted or unsubstituted cyanoaryl group having 6 to 30 carbon atoms;
치환 또는 비치환된 탄소수 6 내지 30개의 플루오로아릴기; A substituted or unsubstituted fluoroaryl group having 6 to 30 carbon atoms;
치환 또는 비치환된 탄소수 11 내지 40개의 헤테로아릴기; A substituted or unsubstituted heteroaryl group having 11 to 40 carbon atoms;
치환 또는 비치환된 탄소수 6 내지 40개의 아미노아릴기; A substituted or unsubstituted aminoaryl group having 6 to 40 carbon atoms;
치환 또는 비치환된 탄소수 5 내지 40개의 아미노헤테로아릴기; A substituted or unsubstituted aminoheteroaryl group having 5 to 40 carbon atoms;
중에서 선택되고,is selected from
상기 Ar1은 The Ar 1 is
치환 또는 비치환된 탄소수 1 내지 40개의 알킬기; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms;
치환 또는 비치환된 탄소수 2 내지 40개의 알킬알콕시기;A substituted or unsubstituted alkyl alkoxy group having 2 to 40 carbon atoms;
치환 또는 비치환된 탄소수 6 내지 40개의 아릴기; A substituted or unsubstituted aryl group having 6 to 40 carbon atoms;
치환 또는 비치환된 탄소수 7 내지 40개의 아릴알킬기; A substituted or unsubstituted arylalkyl group having 7 to 40 carbon atoms;
치환 또는 비치환된 탄소수 6 내지 40개의 아릴아민기; A substituted or unsubstituted arylamine group having 6 to 40 carbon atoms;
치환 또는 비치환된 탄소수 6 내지 30개의 시아노아릴기; A substituted or unsubstituted cyanoaryl group having 6 to 30 carbon atoms;
치환 또는 비치환된 탄소수 6 내지 30개의 플루오로아릴기; A substituted or unsubstituted fluoroaryl group having 6 to 30 carbon atoms;
치환 또는 비치환된 탄소수 11 내지 40개의 헤테로아릴기; A substituted or unsubstituted heteroaryl group having 11 to 40 carbon atoms;
중에서 선택된다.are selected from
상기 화학식 1-1 내지 화학식 1-10의 구체적 구조는 하기 화학식 2-1-1 내지 2-10-2 중 어느 하나로 표시되는 것을 특징으로 하는 말로노나이트릴(malononitrile) 화합물:A malononitrile compound, characterized in that the specific structure of Formula 1-1 to Formula 1-10 is represented by any one of Formulas 2-1-1 to 2-10-2:
[화학식 2-1-1][Formula 2-1-1]
[화학식 2-1-2][Formula 2-1-2]
[화학식 2-1-3][Formula 2-1-3]
[화학식 2-1-4][Formula 2-1-4]
[화학식 2-1-5][Formula 2-1-5]
[화학식 2-1-6][Formula 2-1-6]
[화학식 2-1-7][Formula 2-1-7]
[화학식 2-1-8][Formula 2-1-8]
[화학식 2-2-1][Formula 2-2-1]
[화학식 2-2-2][Formula 2-2-2]
[화학식 2-3-1][Formula 2-3-1]
[화학식 2-3-2][Formula 2-3-2]
[화학식 2-3-3][Formula 2-3-3]
[화학식 2-3-4][Formula 2-3-4]
[화학식 2-4-1][Formula 2-4-1]
[화학식 2-4-2][Formula 2-4-2]
[화학식 2-4-3][Formula 2-4-3]
[화학식 2-5-1][Formula 2-5-1]
[화학식 2-5-2][Formula 2-5-2]
[화학식 2-6-1][Formula 2-6-1]
[화학식 2-6-2][Formula 2-6-2]
[화학식 2-7-1][Formula 2-7-1]
[화학식 2-7-2][Formula 2-7-2]
[화학식 2-7-3][Formula 2-7-3]
[화학식 2-8-1][Formula 2-8-1]
[화학식 2-8-2][Formula 2-8-2]
[화학식 2-8-3][Formula 2-8-3]
[화학식 2-9-1][Formula 2-9-1]
[화학식 2-9-2][Formula 2-9-2]
[화학식 2-10-1][Formula 2-10-1]
[화학식 2-10-2][Formula 2-10-2]
상기 화학식 2-1-1 내지 화학식 2-10-2에서 In Formula 2-1-1 to Formula 2-10-2
상기 R1 내지 R6은 각각 서로 독립적으로 수소; The R 1 to R 6 are each independently hydrogen;
치환 또는 비치환된 탄소수 1 내지 40개의 아릴기; A substituted or unsubstituted aryl group having 1 to 40 carbon atoms;
치환 또는 비치환된 탄소수 1 내지 40개의 아릴알킬기; A substituted or unsubstituted arylalkyl group having 1 to 40 carbon atoms;
치환 또는 비치환된 탄소수 1 내지 40개의 아릴아민기; A substituted or unsubstituted arylamine group having 1 to 40 carbon atoms;
치환 또는 비치환된 탄소수 1 내지 30개의 시아노아릴기; A substituted or unsubstituted cyanoaryl group having 1 to 30 carbon atoms;
치환 또는 비치환된 탄소수 1 내지 30개의 플루오로아릴기; A substituted or unsubstituted fluoroaryl group having 1 to 30 carbon atoms;
치환 또는 비치환된 탄소수 1 내지 40개의 헤테로아릴기; A substituted or unsubstituted heteroaryl group having 1 to 40 carbon atoms;
치환 또는 비치환된 탄소수 1 내지 40개의 헤테로아민아릴기; A substituted or unsubstituted heteroamine aryl group having 1 to 40 carbon atoms;
치환 또는 비치환된 탄소수 1 내지 40개의 아미노아릴기; A substituted or unsubstituted aminoaryl group having 1 to 40 carbon atoms;
치환 또는 비치환된 탄소수 1 내지 40개의 아미노헤테로아릴기; A substituted or unsubstituted aminoheteroaryl group having 1 to 40 carbon atoms;
중에서 선택되고,is selected from
상기 Ar1은 The Ar 1 is
치환 또는 비치환된 탄소수 1 내지 40개의 알킬기; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms;
치환 또는 비치환된 탄소수 1 내지 40개의 아릴기; A substituted or unsubstituted aryl group having 1 to 40 carbon atoms;
치환 또는 비치환된 탄소수 1 내지 40개의 아릴알킬기; A substituted or unsubstituted arylalkyl group having 1 to 40 carbon atoms;
치환 또는 비치환된 탄소수 1 내지 40개의 아릴아민기; A substituted or unsubstituted arylamine group having 1 to 40 carbon atoms;
치환 또는 비치환된 탄소수 1 내지 40개의 헤테로아릴기; A substituted or unsubstituted heteroaryl group having 1 to 40 carbon atoms;
치환 또는 비치환된 탄소수 1 내지 40개의 헤테로아민아릴기; A substituted or unsubstituted heteroamine aryl group having 1 to 40 carbon atoms;
중에서 선택된다.are selected from
상기 화합물은 아래 화합물들 중 어느 하나인 것을 특징으로 한다.The compound is characterized in that any one of the following compounds.
본 발명의 일 측면에 따르면, 제1 전극, 제2 전극 및 이들 전극 사이에 배치된 1층 이상의 유기물 층을 포함하는 유기전자소자로서, 상기 유기물층 중 적어도 1층 이상이 상기 말로노나이트릴(malononitrile) 화합물을 포함하는 유기전자소자가 제공된다.According to one aspect of the present invention, an organic electronic device including a first electrode, a second electrode, and one or more organic material layers disposed between these electrodes, wherein at least one of the organic material layers is malononitrile (malononitrile). ) An organic electronic device including a compound is provided.
상기 말로노나이트릴(malononitrile) 화합물은 단일 물질 또는 서로 다른 물질의 혼합물의 형태로 상기 유기물층에 포함될 수 있다. The malononitrile compound may be included in the organic material layer in the form of a single material or a mixture of different materials.
상기 유기물층은 정공 주입층, 정공 수송층, 정공 주입 기능 및 정공 수송 기능을 동시에 갖는 기능층, 전자 저지층, 발광층, 정공 저지층, 전자 수송층, 전자 주입층 및 전자 수송 기능 및 전자 주입 기능을 동시에 갖는 기능층 중 적어도 하나를 포함할 수 있다. 상기 정공 주입층, 상기 정공 수송층 및 상기 정공 주입 기능 및 정공 수송 기능을 동시에 갖는 기능층 중 적어도 하나는, 통상의 정공 주입 물질, 정공 수송 물질 및 정공 주입 및 수송 기능을 동시에 하는 물질 외에, 전하-생성 물질을 더 포함할 수 있다.The organic material layer is a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function at the same time, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron transport function and an electron injection function. At least one of the functional layers may be included. At least one of the hole injection layer, the hole transport layer, and the functional layer simultaneously having a hole injection function and a hole transport function may include, in addition to a conventional hole injection material, a hole transport material, and a material simultaneously performing hole injection and transport functions, charge- It may further contain a product material.
본 명세서 중 "유기물층"은 유기전자소자 중 제1전극과 제2전극 사이에 개재된 모든 층을 가리키는 용어이다.In the present specification, "organic material layer" is a term indicating all layers interposed between the first electrode and the second electrode in an organic electronic device.
예를 들어, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 인광 호스트, 형광 호스트, 인광 도판트 및 형광 도판트 중 하나 이상을 포함할 수 있다. For example, the organic layer may include a light emitting layer, and the light emitting layer may include at least one of a phosphorescent host, a fluorescent host, a phosphorescent dopant, and a fluorescent dopant.
상기 발광층은 적색, 녹색 또는 청색 발광층일 수 있다. The light emitting layer may be a red, green or blue light emitting layer.
상기 전자 수송층에 상기 말로노나이트릴(malononitrile) 화합물이 포함되어 있으며, 고효율, 고휘도, 고색순도, 및 장수명을 갖는 유기전자소자를 제공할 수 있다.The electron transport layer contains the malononitrile compound, and an organic electronic device having high efficiency, high luminance, high color purity, and long lifespan can be provided.
또한, 상기 말로노나이트릴(malononitrile) 화합물은 상기 발광층, 정공 수송층 및 소자 성능향상의 구조 응용에 포함될 수 있다.In addition, the malononitrile compound may be included in structural applications of the light emitting layer, hole transport layer, and device performance improvement.
상기 유기전자소자는 상기 말로노나이트릴(malononitrile) 화합물을 이용하는 것을 제외하고는, 통상의 유기전자소자의 제조방법 및 재료에 의하여 제조될 수 있다.The organic electronic device may be manufactured by conventional organic electronic device manufacturing methods and materials, except for using the malononitrile compound.
본 발명의 일 측면에 따른 구체예로써, 상기 유기전자소자는 유기발광소자 (OLED), 유기태양전지 (OSC), 전자종이 (e-Paper), 유기감광체(OPC) 또는 유기트랜지스터 (OTFT)일 수 있다.As a specific example according to one aspect of the present invention, the organic electronic device may be an organic light emitting device (OLED), an organic solar cell (OSC), an electronic paper (e-Paper), an organic photoreceptor (OPC) or an organic transistor (OTFT). can
유기발광소자는 스퍼터링(sputtering)이나 전자빔 증발(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 정공주입층, 정공전달층, 발광층, 정공저지층 및 전자전달층을 포함하는 유기물 층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착 시킴으로써 제조될 수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물층, 양극 물질을 차례로 증착시켜 유기발광소자를 만들 수도 있다. 상기 유기물 층은 정공주입층, 정공전달층, 발광층, 정공저지층 및 전자전달층 등을 포함하는 다층 구조일 수도 있다. 또한, 상기 유기물 층은 다양한 고분자 소재를 사용하여 증착법이 아닌 용매 공정(solvent process), 예컨대 스핀 코팅, 딥 코팅, 닥터 블레이딩, 스크린 프린팅, 잉크젯 프린팅 또는 열전사법 등의 방법에 의하여 더 적은 수의 층으로 제조할 수 있다.The organic light emitting device uses a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form an anode by depositing a metal or conductive metal oxide or an alloy thereof on a substrate. And, after forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer and an electron transport layer thereon, depositing a material that can be used as a cathode thereon. In addition to this method, an organic light emitting device may be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate. The organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, and an electron transport layer. In addition, the organic layer can be formed by using various polymer materials and using a solvent process other than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. Can be made in layers.
본 발명에 따른 유기발광소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다. 본 발명에 따른 화합물은 유기태양전지, 조명용 OLED, Flexible OLED, 유기감광체, 유기트랜지스터 등을 비롯한 유기전자소자에서도 유기발광소자에 적용되는 것과 유사한 원리로 작용할 수 있다. The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a double side emission type depending on the material used. The compound according to the present invention may act on a principle similar to that applied to an organic light emitting device in organic electronic devices including organic solar cells, lighting OLEDs, flexible OLEDs, organic photoreceptors, organic transistors, and the like.
이하, 본 발명의 이해를 돕기 위하여 바람직한 실시예를 제시한다. 그러나 하기의 실시예는 본 발명을 보다 쉽게 이해하기 위하여 제공되는 것일 뿐, 이에 의해 본 발명의 내용이 한정되는 것은 아니다. Hereinafter, a preferred embodiment is presented to aid understanding of the present invention. However, the following examples are only provided to more easily understand the present invention, and the content of the present invention is not limited thereby.
또한, 본 발명의 각 실시예에서 제조방법이 구체적으로 개시되지 않은 화합물은 당업계에 통상적인 방법으로 제조하거나 또는 다른 실시예에 기재된 제조방법을 참고하여 제조함을 이해한다.In addition, it is understood that compounds for which preparation methods are not specifically disclosed in each embodiment of the present invention are prepared by conventional methods in the art or with reference to preparation methods described in other embodiments.
<중간체의 제조><Preparation of intermediates>
1-1 중간체 2-bromo-11H-benzo[b]fluoren-11-one의 제조 Preparation of 1-1 intermediate 2-bromo-11H-benzo[b]fluoren-11-one
11H-benzo[b]fluoren-11-one (23.03g, 0.1 mol)과 Propylene carbonate (100 mL)에 녹인 후, N-bromo succinimide (17.8g, 0.1mol)을 넣고, 60℃에서 30분 동안 교반하였다. 반응을 실온으로 냉각시킨 후, 물 (1200 mL)희석하고 500 mL의 toluene으로 추출했으며, 유기물을 무수유산 마그네슘으로 건조시킨 후, 혼합물을 여과 농축하여 최종 화합물 (24.73g，80%）을 얻었다. MS [M+H]+ = 307Dissolve 11H-benzo[b]fluoren-11-one (23.03g, 0.1 mol) and Propylene carbonate (100 mL), add N-bromo succinimide (17.8g, 0.1mol), and stir at 60℃ for 30 minutes did After cooling the reaction to room temperature, it was diluted with water (1200 mL), extracted with 500 mL of toluene, and the organic matter was dried over anhydrous magnesium lactate, and the mixture was concentrated by filtration to obtain the final compound (24.73 g, 80%). MS [M+H] + = 307
1-2 중간체 4,5,9,10-tetrabromoisochromeno[6,5,4-def]isochromene-1,3,6,8-tetraone의 제조Preparation of 1-2 intermediate 4,5,9,10-tetrabromoisochromeno[6,5,4-def]isochromene-1,3,6,8-tetraone
isochromeno[6,5,4-def]isochromene-1,3,6,8-tetraone(26.82g, 0.1 mol)과 Propylene carbonate (200 mL)에 녹인 후, N-bromo succinimide (71.2g, 0.4mol)을 넣고, 60℃에서 30분 동안 교반하였다. 반응을 실온으로 냉각시킨 후, 물 (1200 mL)희석하고 500 mL의 toluene으로 추출했으며, 유기물을 무수유산 마그네슘으로 건조시킨 후, 혼합물을 여과 농축하여 최종 화합물 (35.03g，60%）을 얻었다. MS [M+H]+ = 580After dissolving isochromeno[6,5,4-def]isochromene-1,3,6,8-tetraone (26.82g, 0.1 mol) and propylene carbonate (200 mL), N-bromo succinimide (71.2g, 0.4mol) was added and stirred at 60° C. for 30 minutes. After cooling the reaction to room temperature, it was diluted with water (1200 mL), extracted with 500 mL of toluene, and the organic matter was dried over anhydrous magnesium lactate, and the mixture was filtered and concentrated to obtain the final compound (35.03 g, 60%). MS [M+H] + = 580
2-1 중간체 2-(2-bromo-11H-benzo[b]fluoren-11-ylidene)malononitrile의 제조Preparation of 2-1 intermediate 2-(2-bromo-11H-benzo[b]fluoren-11-ylidene)malononitrile
500ml 둥근 바닥 플라스크에 화합물2-bromo-11H-benzo[b]fluoren-11-one (4.641g, 15.0mmol), 말로노나이트릴(malononitrile)(30.0mmol) 및 디 클로로메테인 용매를 넣고 아르곤 조건 하에서 30분간 교반 한다. 0℃로 냉각하여 10분간 교반 후 사염화티타늄 (TiCl4)(3.28ml, 30m mol)을 천천히 넣어준 후 피리딘(7.40ml, 9.2mmol)을 넣고 0℃에서 상온으로 천천히 온도를 올려 상온에서 2시간 교반시킨다. 이후 디클로로메탄/염화암모늄 수용액(CH2Cl2/aq.NH4Cl)으로 추출한 후에 유기물층을 무수황산마그네슘으로 건조시키고 유기층을 모아 감압하에서 증류하여 컬럼크로마토그래피를 이용하여 최종 화합물 （2.14g, 수율 40%)을 얻었다. MS [M+H]+ 357Compound 2-bromo-11H-benzo[b]fluoren-11-one (4.641g, 15.0mmol), malononitrile (30.0mmol) and dichloromethane solvent were added to a 500ml round bottom flask under argon condition. Stir for 30 minutes under After cooling to 0℃ and stirring for 10 minutes, titanium tetrachloride (TiCl 4 ) (3.28ml, 30m mol) was slowly added, pyridine (7.40ml, 9.2mmol) was added, and the temperature was slowly raised from 0℃ to room temperature for 2 hours at room temperature. Stir. After extraction with dichloromethane/ammonium chloride aqueous solution (CH 2 Cl 2 /aq.NH 4 Cl), the organic layer was dried over anhydrous magnesium sulfate, and the organic layer was collected and distilled under reduced pressure to determine the final compound (2.14 g, yield) using column chromatography. 40%) was obtained. MS [M+H] + 357
2-2 중간체 2,2'-(3-chlorocyclohexa-3,5-diene-1,2-diylidene)dimalononitrile의 제조Preparation of 2-2 intermediate 2,2'-(3-chlorocyclohexa-3,5-diene-1,2-diylidene)dimalononitrile
500ml 둥근 바닥 플라스크에 화합물isoindoline-1,3-dione(2.21g, 15.0mmol), 말로노나이트릴(malononitrile)(60.0mmol) 및 디 클로로메테인 용매를 넣고 아르곤 조건 하에서 30분간 교반 한다. 0℃로 냉각하여 10분간 교반 후 사염화티타늄 (TiCl4)(6.56ml, 60m mol)을 천천히 넣어준 후 피리딘(7.40ml, 9.2mmol)을 넣고 0℃에서 상온으로 천천히 온도를 올려 상온에서 2시간 교반시킨다. 이후 디클로로메탄/염화암모늄 수용액(CH2Cl2/aq.NH4Cl)으로 추출한 후에 유기물층을 무수황산마그네슘으로 건조시키고 유기층을 모아 감압하에서 증류하여 컬럼크로마토그래피를 이용하여 최종 화합물 (1.64g, 수율 45.0%)을 얻는다. MS [M+H]+ = 238Put the compound isoindoline-1,3-dione (2.21g, 15.0mmol), malononitrile (60.0mmol) and dichloromethane solvent in a 500ml round bottom flask and stir for 30 minutes under argon conditions. After cooling to 0℃ and stirring for 10 minutes, titanium tetrachloride (TiCl 4 ) (6.56ml, 60m mol) was slowly added, pyridine (7.40ml, 9.2mmol) was added, and the temperature was slowly raised from 0℃ to room temperature for 2 hours at room temperature. Stir. After extraction with dichloromethane/ammonium chloride aqueous solution (CH 2 Cl 2 /aq.NH 4 Cl), the organic layer was dried over anhydrous magnesium sulfate, and the organic layer was collected and distilled under reduced pressure to obtain the final compound (1.64 g, yield) using column chromatography. 45.0%). MS [M+H] + = 238
3-1 중간체(11-(dicyanomethylene)-11H-benzo[b]fluoren-2-yl)boronic acid의 제조Preparation of 3-1 intermediate (11-(dicyanomethylene)-11H-benzo[b]fluoren-2-yl)boronic acid
질소 보호 하에 3 구 플라스크에 THF (500mL)을 반응 용기에 넣고 2-(2-bromo-11H-benzo[b]fluoren-11-ylidene)malononitrile (30.61g, 85.7mmol), 질소 및 -78℃ 조건하에서 30분 동안 교반한다. butyl lithium （1.25 M/72mL）을 넣고, 1h 교반 후, Triisopropyl borate (17.03g, 90mmol)를 넣고, 낮은 온도에서 1h 교반하고, 점차 실온으로 회복한다. 2M 염산을 넣어 PH를 4-5로 조절한 다음 반응을 정지시킨다. 유기상을 취하고 무수황산마그네슘으로 건조시킨다. 건조된 혼합물을 여과하고 감압 농축한 후 실리카겔 크로마토 그래피 컬럼 또는 증류법으로 정제하여 최종 화합물 (16.56g, 수율 60%)을 얻었다. MS [M+H]+ 322THF (500 mL) was added to the reaction vessel in a three-necked flask under nitrogen protection and 2-(2-bromo-11H-benzo[b]fluoren-11-ylidene)malononitrile (30.61g, 85.7mmol), nitrogen and -78℃ conditions. Stir for 30 minutes under Add butyl lithium (1.25 M/72mL), stir for 1h, add Triisopropyl borate (17.03g, 90mmol), stir for 1h at low temperature, and gradually return to room temperature. 2M hydrochloric acid was added to adjust the pH to 4-5, and then the reaction was stopped. The organic phase is taken and dried over anhydrous magnesium sulfate. The dried mixture was filtered, concentrated under reduced pressure, and purified by silica gel chromatography column or distillation to obtain the final compound (16.56 g, yield 60%). MS [M+H] + 322
3-2 중간체 (5,6-bis(dicyanomethylene)cyclohexa-1,3-dien-1-yl)boronic acid의 제조Preparation of 3-2 intermediate (5,6-bis(dicyanomethylene)cyclohexa-1,3-dien-1-yl)boronic acid
질소 보호 하에 3 구 플라스크에 THF (500mL)을 반응 용기에 넣고 3-chlorocyclohexa-3,5-diene-1,2-dione (21.52g, 85.7mmol), 질소 및 -78℃ 조건하에서 30분 동안 교반한다. butyl lithium （1.25 M/72mL）을 넣고, 1h 교반 후, Triisopropyl borate (17.03g, 90mmol)를 넣고, 낮은 온도에서 1h 교반하고, 점차 실온으로 회복한다. 2M 염산을 넣어 PH를 4-5로 조절한 다음 반응을 정지시킨다. 유기상을 취하고 무수황산마그네슘으로 건조시킨다. 건조 된 혼합물을 여과하고 감압 농축 한 후 실리카겔 크로마토 그래피 컬럼 또는 증류법으로 정제하여 최종 화합물 (14.32g, 수율 : 70 %)를 얻었다. MS [M+H]+ = 248THF (500mL) was added to the reaction vessel in a three-necked flask under nitrogen protection, and 3-chlorocyclohexa-3,5-diene-1,2-dione (21.52g, 85.7mmol) was stirred for 30 minutes under nitrogen and -78℃ conditions. do. Add butyl lithium (1.25 M/72mL), stir for 1h, add Triisopropyl borate (17.03g, 90mmol), stir at low temperature for 1h, and gradually return to room temperature. 2M hydrochloric acid was added to adjust the pH to 4-5, and then the reaction was stopped. The organic phase is taken and dried over anhydrous magnesium sulfate. The dried mixture was filtered, concentrated under reduced pressure, and purified by silica gel chromatography column or distillation method to obtain the final compound (14.32 g, yield: 70%). MS [M+H] + = 248
4-1 2,2'-(4'-(10-phenylanthracen-9-yl)-[1,1'-biphenyl]-2,3-diylidene)dimalononitri le의 제조Preparation of 4-1 2,2'-(4'-(10-phenylanthracen-9-yl)-[1,1'-biphenyl]-2,3-diylidene)dimalononitri le
질소조건하에서 (5,6-bis(dicyanomethylene)cyclohexa-1,3-dien-1-yl)boronic acid9.92g，40mmol), 9-(4-bromophenyl)-10-phenylanthracene（16.32g ，160mmol）, 테트라하이드로퓨란 400mL 및 물 200mL를 혼합하고 60℃로 가열하였다. 포타슘카보네이트 480mmol 및 테트라키스트라이페닐포스핀팔라듐(0.2mmol)을 첨가 하여 리플럭스 상태로 6시간 교반하였다. 반응 후 실온으로 되돌린 반응 용액에서 유기층을 추출한 후, 클로로 포름과 헥산으로 2회 재결정을 실시하여, 최종 화합물 (11.31g,54 %)을 얻었다. MS [M+H]+ = 532Under nitrogen conditions, (5,6-bis(dicyanomethylene)cyclohexa-1,3-dien-1-yl)boronic acid9.92g，40mmol), 9-(4-bromophenyl)-10-phenylanthracene（16.32g，160mmol）, 400 mL of tetrahydrofuran and 200 mL of water were mixed and heated to 60°C. After adding 480 mmol of potassium carbonate and tetrakistriphenylphosphine palladium (0.2 mmol), the mixture was stirred for 6 hours in a reflux state. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then recrystallized twice with chloroform and hexane to obtain the final compound (11.31 g, 54%). MS [M+H] + = 532
4-2 중간체 2,2'-(3-(bis(4-isopropylphenyl)amino)cyclohexa-3,5-diene-1,2-diylidene) dimalononitrile의 제조Preparation of 4-2 intermediate 2,2'-(3-(bis(4-isopropylphenyl)amino)cyclohexa-3,5-diene-1,2-diylidene) dimalononitrile
질소조건하에서 중간체 2,2'-(3-chlorocyclohexa-3,5-diene-1,2-diylidene)dimalo nonitrile (3.39g, 10mmol), bis(4-isopropylphenyl)amine(2.53g, 10mmol), Sodium tert-butoxide (1.3g, 13.5mmol), Tris (dibenzylideneacetone) dipalladium (0.046g, 0.05mmol), tri-tert-butylphosphine (0.021g, 0.1mmol) 및 탈수 톨루엔 (50ml)을 80℃에서 2h 동안 반응시켰다. 냉각 후 물 (500ml)을 가하고 혼합물을 여과하고, 여액을 톨루엔으로 추출하고, 유기상을 무수 황산 마그네슘으로 건조시켰다. 감압 농축하고, 생성된 생성물을 컬럼 정제한 후, 톨루엔으로 재결정 및 여과 건조하여 최종 화합물（3.50g, 75%)을 얻었다. MS [M+H]+ = 455Intermediate 2,2'-(3-chlorocyclohexa-3,5-diene-1,2-diylidene)dimalo nonitrile (3.39g, 10mmol), bis(4-isopropylphenyl)amine (2.53g, 10mmol), sodium under nitrogen conditions tert-butoxide (1.3g, 13.5mmol), Tris (dibenzylideneacetone) dipalladium (0.046g, 0.05mmol), tri-tert-butylphosphine (0.021g, 0.1mmol) and dehydrated toluene (50ml) were reacted at 80℃ for 2h. . After cooling, water (500 ml) was added and the mixture was filtered, the filtrate was extracted with toluene, and the organic phase was dried over anhydrous magnesium sulfate. After concentration under reduced pressure and column purification, the resulting product was recrystallized from toluene and filtered to dry to obtain the final compound (3.50 g, 75%). MS [M+H] + = 455
<화합물의 제조><Preparation of compound>
* 화합물 a-1 내지 a-40의 제조* Preparation of compounds a-1 to a-40
상기 1-1과 1-2 및 당량 조절방법을 이용하여 하기 [표 1]의 화합물을 얻었다:Using the above 1-1 and 1-2 and the equivalent control method, the compounds of [Table 1] were obtained:
* 화합물 a-1-1 내지 a-1-5의 제조* Preparation of compounds a-1-1 to a-1-5
상기 4-1 및 당량 조절방법을 이용하여 하기 [표 2]의 화합물을 얻었다:Using the above 4-1 and the equivalent control method, the compounds of [Table 2] were obtained:
* 화합물 b-1 내지 b-35의 제조* Preparation of compounds b-1 to b-35
상기 3-1과 3-2 및 당량 조절방법을 이용하여 하기 [표 3]의 화합물을 얻었다:Using the above 3-1 and 3-2 and the equivalent control method, the compounds of [Table 3] were obtained:
* 실시예 A-1 내지 A-114의 제조* Preparation of Examples A-1 to A-114
상기 표 1 내지 3의 화합물 및 당량 조절방법을 이용하여 하기 [표 4]의 화합물을 얻었다:Using the compounds and equivalents of Tables 1 to 3 above, the following [Table 4] compounds were obtained:
1 One
* 실시예 B-1 내지 B-125의 제조* Preparation of Examples B-1 to B-125
상기 표 1 내지 3의 화합물 및 당량 조절방법을 이용하여 하기 [표 5]의 화합물을 얻었다:Using the compounds of Tables 1 to 3 and the equivalent weight control method, the compounds of [Table 5] were obtained:
<실험예><Experimental example>
ITO가 1500Å의 두께로 박막 코팅된 유리 기판을 피셔사의 세제를 녹인 2차 증류수에 넣고 초음파로 30분간 세척하였다. ITO를 30 분간 세척한 후 증류수로 2 회 반복하여 초음파 세척을 10 분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척하고 건조시킨 후, 플라즈마 세정기로 이송시켜, 산소 플라즈마를 이용하여 상기 기판을 5 분간 세정한 후 진공 증착기로 기판을 이송시켰다.A glass substrate coated with a thin film of ITO to a thickness of 1500 Å was placed in double distilled water in which Fisher's detergent was dissolved and washed with ultrasonic waves for 30 minutes. After washing the ITO for 30 minutes, ultrasonic cleaning was performed twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning with solvents such as isopropyl alcohol, acetone, and methanol, and drying, the substrate was transferred to a plasma cleaner, and the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transferred to a vacuum evaporator.
이렇게 준비된 ITO 투명 전극 위에 정공주입층으로 2-TNATA (4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine)를 500Å 진공증착 후, 정공전달층으로 a-NPD (N,N'-Di(1-naphthyl)-N,N'-diphenyl-(1,1'-ciphenyl)-4,4'-diamine) 300Å 진공 증착한 후, 청색 물질의 경우 청색 호스트로 AND (9,10-Di(2-naphthyl)anthracene)에 도판트 DPAP-DPPA (6-(4-(diphenylamino)phenyl)-N,N-diphenylpyren-1-amine) 5%를 도핑하였으며, 적색의 경우 RH-01 (9-phenyl-9'-(4-phenylquinazolin-2-yl)-9H,9'H-3,3'-cicarcazole)에 RD-01 (5,6,11,12-tetraphenyltetracene) 5%를 도핑하여 300Å의 두께로 진공 증착하였다. 그리고 정공저지층 및 정공전달층으로 TPBi 2,2',2''-(1,3,5-Benzinetriyl)-tris(1-phenyl-1-H-benzimidazole) 물질을 400Å의 두께로 진공 증착 하였으며, 순차적으로 LiF 5Å과 Al(알루미늄) 2000Å 증착하여 음극을 형성하였다. After vacuum deposition of 500Å of 2-TNATA (4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine) as a hole injection layer on the prepared ITO transparent electrode, a-NPD (N, After vacuum deposition of N'-Di(1-naphthyl)-N,N'-diphenyl-(1,1'-ciphenyl)-4,4'-diamine) 300Å, AND (9, 10-Di(2-naphthyl)anthracene) was doped with 5% of the dopant DPAP-DPPA (6-(4-(diphenylamino)phenyl)-N,N-diphenylpyren-1-amine), and in the case of red, RH-01 (9-phenyl-9'-(4-phenylquinazolin-2-yl)-9H,9'H-3,3'-cicarcazole) doped with 5% of RD-01 (5,6,11,12-tetraphenyltetracene) TPBi 2,2',2''-(1,3,5-Benzinetriyl)-tris(1-phenyl-1-H-benzimidazole) was used as a hole blocking layer and a hole transporting layer. The material was vacuum deposited to a thickness of 400 Å, and a cathode was formed by sequentially depositing 5 Å of LiF and 2000 Å of Al (aluminum).
상기 내용에서 실시예를 이용한 비교실험은 하기와 같다.In the above content, comparative experiments using examples are as follows.
1) AND과 DPAP-DPPA 청색 발광에서 HIL (2-TNATA) 비교 실험은 표 61) Table 6 for comparison of HIL (2-TNATA) in AND and DPAP-DPPA blue light emission
2) AND과 DPAP-DPPA 청색 발광에서 ETL (TPBi) 비교실험은 표 72) Comparison of ETL (TPBi) in AND and DPAP-DPPA blue light emission is shown in Table 7.
3) RH01과 RD01적색 발광에서 도판트 (RD-01) 비교 실험은 표 83) Dopant (RD-01) comparison experiment in RH01 and RD01 red light emission is shown in Table 8
상기 발명으로 기재된 실시예의 일부 물질의 성능을 비교하였다.The performance of some of the materials of the examples described above was compared.
상기의 과정에서 유기물의 증착속도는 1 Å/sec를 유지하였고, LiF는 0.2 Å/sec, 알루미늄은 3~7Å/sec의 증착속도를 유지하였다.In the above process, the deposition rate of the organic material was maintained at 1 Å/sec, LiF was maintained at 0.2 Å/sec, and aluminum was maintained at a deposition rate of 3 to 7 Å/sec.
상기에서 제조된 유기 발광 소자에 대한 전기적 발광특성을 하기에 나타내었다.Electrical emission characteristics of the organic light emitting device prepared above are shown below.
청색 발광에서 AND 호스트와 DPAP-DPPA 상태에서 2-TNATA와 실시예의 정공주입층 (HIL) 성능 비교하여 아래 표 6에 나타내었다.In blue light emission, the performance of the hole injection layer (HIL) of 2-TNATA and Examples in the state of AND host and DPAP-DPPA was compared and shown in Table 6 below.
청색 발광에서 AND 호스트와 DPAP-DPPA 상태에서 TPBi와 실시예의 전자전달층 (ETL) 성능 비교하여 아래 표 7에 나타내었다.In blue light emission, the performance of the electron transport layer (ETL) of TPBi and Examples in the state of AND host and DPAP-DPPA was compared and shown in Table 7 below.
적색 발광의 RH-01/RD-01 상태에서 RD-01와 실시예의 성능 비교하여 아래 표 8에 나타내었다.Performance comparison of RD-01 and Example in the state of RH-01/RD-01 of red light emission is shown in Table 8 below.
상기 표 6 내지 표 8의 결과로부터, 본 발명에 따른 말로노나이트릴(malononitrile) 화합물은 정공주입의 HIL과 전자전달의 ETL 및 적색 발광의 Dopant에서 성능 향상 결과를 얻었으며, 청색 발광의 HIL과 ETL 응용성 및 소자의 수명 특성이 향상됨을 확인할 수 있었다.From the results of Tables 6 to 8, the malononitrile compound according to the present invention obtained performance improvement results in HIL of hole injection, ETL of electron transfer, and Dopant of red light emission, and HIL and blue light emission. It was confirmed that the ETL applicability and lifespan characteristics of the device were improved.
본 발명의 말로노나이트릴(malononitrile) 화합물을 이용한 유기발광소자는 발광 효율과 수명이 우수한 향상을 얻을 수 있었다. 이 때문에, 실용성이 높은 OLED로서 산업적으로 유용하다. The organic light emitting device using the malononitrile compound of the present invention was able to obtain excellent improvement in light emitting efficiency and lifespan. For this reason, it is industrially useful as an OLED with high practicality.
본 발명의 유기발광소자는 평면 패널 디스플레이, 평면 발광체, 조명용 면발광 OLED의 발광체, flexible 발광체, 복사기, 프린터, LCD 백라이트 또는 계량기류 등의 광원, 디스플레이판, 표식등 등에 적합하게 이용할 수 있다.The organic light emitting device of the present invention can be suitably used for light sources such as flat panel displays, flat light emitting bodies, surface light emitting OLED light emitting bodies for lighting, flexible light emitting bodies, copiers, printers, LCD backlights or meters, display boards, signs, etc.
Claims (6)
[화학식 1-9]
상기 R1 내지 R4은 각각 서로 독립적으로 수소;
탄소수 1 내지 40개의 알킬기;
탄소수 2 내지 40개의 알킬알콕시기;
탄소수 6 내지 40개의 아릴기;
탄소수 7 내지 40개의 아릴알킬기;
탄소수 6 내지 40개의 아릴아민기;
탄소수 6 내지 30개의 시아노아릴기;
탄소수 6 내지 30개의 플루오로아릴기;
탄소수 11 내지 40개의 헤테로아릴기;
탄소수 6 내지 40개의 아미노아릴기;
탄소수 5 내지 40개의 아미노헤테로아릴기;
중에서 선택된다.A malononitrile compound represented by Formula 1-9:
[Formula 1-9]
The R 1 to R 4 are each independently hydrogen;
an alkyl group having 1 to 40 carbon atoms;
an alkylalkoxy group having 2 to 40 carbon atoms;
an aryl group having 6 to 40 carbon atoms;
an arylalkyl group having 7 to 40 carbon atoms;
an arylamine group having 6 to 40 carbon atoms;
A cyanoaryl group having 6 to 30 carbon atoms;
A fluoroaryl group having 6 to 30 carbon atoms;
a heteroaryl group having 11 to 40 carbon atoms;
an aminoaryl group having 6 to 40 carbon atoms;
an aminoheteroaryl group having 5 to 40 carbon atoms;
are selected from
상기 화학식 1-9의 구체적 구조는 하기 화학식 2-9-1 내지 2-9-2 중 어느 하나로 표시되는 것을 특징으로 하는 말로노나이트릴(malononitrile) 화합물:
[화학식 2-9-1]
[화학식 2-9-2]
상기 화학식 2-9-1 내지 화학식 2-9-2에서
상기 R1 또는 R3은 각각 서로 독립적으로 수소;
탄소수 1 내지 40개의 아릴기;
탄소수 1 내지 40개의 아릴알킬기;
탄소수 1 내지 40개의 아릴아민기;
탄소수 1 내지 30개의 시아노아릴기;
탄소수 1 내지 30개의 플루오로아릴기;
탄소수 1 내지 40개의 헤테로아릴기;
탄소수 1 내지 40개의 헤테로아민아릴기;
탄소수 1 내지 40개의 아미노아릴기;
탄소수 1 내지 40개의 아미노헤테로아릴기;
중에서 선택된다.According to claim 1,
A malononitrile compound, characterized in that the specific structure of Formula 1-9 is represented by any one of Formulas 2-9-1 to 2-9-2:
[Formula 2-9-1]
[Formula 2-9-2]
In Formula 2-9-1 to Formula 2-9-2
The R 1 or R 3 are each independently hydrogen;
an aryl group having 1 to 40 carbon atoms;
an arylalkyl group having 1 to 40 carbon atoms;
an arylamine group having 1 to 40 carbon atoms;
a cyanoaryl group having 1 to 30 carbon atoms;
A fluoroaryl group having 1 to 30 carbon atoms;
a heteroaryl group having 1 to 40 carbon atoms;
A heteroamine aryl group having 1 to 40 carbon atoms;
an aminoaryl group having 1 to 40 carbon atoms;
an aminoheteroaryl group having 1 to 40 carbon atoms;
are selected from
상기 화합물은 아래 화합물들 중 어느 하나인 것을 특징으로 하는 화합물:
According to claim 1 or 2,
A compound, characterized in that the compound is any one of the following compounds:
상기 유기물층 중 적어도 1층 이상이 제 1 항의 말로노나이트릴(malononitrile) 화합물을 포함하는 유기전자소자. An organic electronic device comprising a first electrode, a second electrode, and one or more organic material layers disposed between these electrodes,
At least one layer of the organic material layer contains the malononitrile compound of claim 1 An organic electronic device containing
상기 유기물층은 정공 주입층, 정공 수송층, 정공 주입 기능 및 정공 수송 기능을 동시에 갖는 기능층, 전자 저지층, 발광층, 정공 저지층, 전자 수송층, 전자 주입층, 및 전자 수송 기능 및 전자 주입 기능을 동시에 갖는 기능층 중 적어도 하나를 포함하는 유기전자소자.According to claim 4,
The organic material layer is a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron transport function and an electron injection function at the same time. An organic electronic device comprising at least one of the functional layers having
상기 유기전자소자가 유기발광소자 (OLED), 유기태양전지 (OSC), 전자종이 (e-Paper), 유기감광체(OPC) 또는 유기트랜지스터 (OTFT)인 유기전자소자.According to claim 5,
An organic electronic device in which the organic electronic device is an organic light emitting device (OLED), an organic solar cell (OSC), an electronic paper (e-Paper), an organic photoreceptor (OPC), or an organic transistor (OTFT).
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| CN112876382A (en) | 2019-11-29 | 2021-06-01 | 广州华睿光电材料有限公司 | Organic compounds, mixtures, compositions and uses thereof |
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