CN114874169A - Organic compound, material comprising the same, and organic light-emitting device - Google Patents
Organic compound, material comprising the same, and organic light-emitting device Download PDFInfo
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- CN114874169A CN114874169A CN202210268082.2A CN202210268082A CN114874169A CN 114874169 A CN114874169 A CN 114874169A CN 202210268082 A CN202210268082 A CN 202210268082A CN 114874169 A CN114874169 A CN 114874169A
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- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 17
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- 125000004429 atom Chemical group 0.000 claims abstract description 8
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- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims abstract description 7
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Classifications
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- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
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Abstract
Disclosed are an organic compound having the formulaStructure shown, X 1 ‑X 4 Selected from O, S, -SO 2 ‑、‑SO‑、‑CR 1 R 2 ‑、‑NR 3 ‑、‑SiR 4 R 5 ‑、‑SeR 6 R 7 ‑;X 1 And X 2 May also be a single bond, Ar 1 And Ar 2 Selected from any one of S1-S26, Ar 3 ‑Ar 5 Selected from C6-C60 aryl, and Ar 3 Is not phenyl; x 5 Selected from O, S, -NR 15 ‑、‑CR 16 R 17 ‑;R 1 ‑R 17 Selected from hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, or a ring bonded to an adjacent atom. The organic compound can be used as a cover material for an organic light-emitting device, which can realize high luminous efficiency and high color purity, for example, in the case of an organic EL display or a light source for illumination, a sign board, a marker lamp, and the like.
Description
Technical Field
The present invention relates to the field of organic photoelectric materials, and more particularly, to an organic compound for an organic light emitting device, a light emitting device material containing the organic compound, and a light emitting device, and more particularly, to a soluble organic compound having excellent color purity, high luminance, and high luminous efficiency, and an OLED device using the same.
Background
Organic Light-Emitting diodes (OLEDs) are attracting attention because they are thin and capable of Emitting Light with high luminance at low driving voltage and also capable of Emitting Light in multiple colors by selecting Light-Emitting materials. Since the organic thin film element was disclosed by kodak company c.w.tang et al to emit light with high brightness, a great deal of research and advancement has been made on its application by a large number of researchers in the OLED industry. Organic thin film light emitting devices are widely used in various main displays and the like, and their practical use has been advanced. Although the research on organic electroluminescence is rapidly progressing, there are still many problems to be solved, and the efficient use of light emission and the reduction of light emission loss are a great problem.
The OLED can be classified into a bottom emission organic light emitting device and a top emission organic light emitting device according to a light emitting manner of the OLED. The initial OLEDs were bottom-emitting devices, which were constructed from top to bottom as follows: opaque metal cathode/organic functional layer/transparent anode, light exits from the anode and is called bottom emission. Top-emitting OLEDs refer to OLEDs in which light is emitted from the top of the device. The top-emitting OLED is not influenced by whether the substrate is transparent or not, so that the aperture opening ratio of the display panel can be effectively improved, the design of a TFT circuit on the substrate is expanded, the selection of electrode materials is enriched, and the integration of a device and the TFT circuit is facilitated. If the device emits light in a bottom emission manner, the light is blocked by TF and metal wiring on the substrate when passing through the substrate, which affects the actual light emitting area. If the light rays are emitted from the upper part of the device, and a top emission device structure is adopted, the light emitting area of the device cannot be influenced by the circuit design of the substrate, the working voltage of the OLED is lower under the same brightness, and the longer service life can be obtained. Therefore, top-emitting devices are the first choice for small pixel, high PPI, small screen active displays such as cell phones.
In the prior art, in order to improve the light extraction efficiency of a top-emission organic light-emitting device, a method is adopted in which an organic cover layer is formed on an upper semi-transparent metal electrode through which light of a light-emitting layer is transmitted, thus, the optical interference distance is adjusted to suppress reflection of external light and extinction by surface plasmon energy transfer (see patent documents 1 to 5, patent document 1: WO2001/039554, patent document 2: CN105849113B, patent document 3: JP2007-103303, patent document 4: CN 109535125, and patent document 5: CN 103579521). for example, patent document 2 describes that the material of the organic coating layer used is an aromatic amine compound having a specific chemical structure or the like, patent document 4 describes that the material of the organic coating layer used is a compound having a dibenzohexatomic ring as a core, and patent document 5 describes that the material of the organic coating layer used is an aromatic amine compound containing fluorene or the like.
Disclosure of Invention
As described above, in the prior art, the light extraction efficiency and the color purity are improved by using an aromatic amine derivative having a specific structure with a high refractive index or using a material satisfying specific parameter requirements as an organic capping layer material, but the problem of achieving both the light emission efficiency and the color purity has not been solved, particularly in the case of manufacturing a blue light emitting element.
The present invention provides an organic compound for improving light extraction efficiency of an organic light emitting element and improving color purity, an organic light emitting element material containing the compound, and an organic device. The organic electroluminescent device containing the organic compound has the advantages of good thermal stability, high luminous efficiency and long service life.
The present invention provides an organic compound having a structure represented by the following formula (1):
in the formula (1), X 1 And X 2 Identical or different, independently selected from the group consisting of single bond, O, S, -SO 2 -、-SO-、-CR 1 R 2 -、-NR 3 -、-SiR 4 R 5 -、-SeR 6 R 7 -;
X 3 And X 4 Identical or different, independently selected from O, S, -SO 2 -、-SO-、-CR 8 R 9 -、-NR 10 -、-SiR 11 R 12 -、-SeR 13 R 14 -;
Ar 1 And Ar 2 The same or different, independently selected from any one of the following substituent groups:
wherein Ar is 3 、Ar 4 And Ar 5 Independently selected from substituted or unsubstituted C6-C60 aryl, and Ar 3 Is not phenyl;
X 5 selected from O, S, -NR 15 -、-CR 16 R 17 -;
R 1 -R 17 Identical or different, independently selected from hydrogen, deuterium, cyano, substitutedOr unsubstituted C1-C60 alkyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C60 heteroalkyl, substituted or unsubstituted C3-C60 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C5-C60 heteroaryl, or bonded to an adjacent atom to form a ring;
denotes the attachment position of the substituent.
The organic compound of the present invention can be used as a capping layer material of an organic light emitting device to achieve high light emitting efficiency and color purity. The organic light-emitting device can be an organic photovoltaic device, an organic electroluminescent device, an organic solar cell, electronic paper, an organic photoreceptor or an organic thin film transistor, can also be used for display or illumination devices, such as organic EL displays or illumination light sources, marking plates, marking lamps and other occasions, and has long service life.
Detailed Description
The invention provides an organic compound, which has a structure shown in the following formula (1):
in the formula (1), X 1 And X 2 Identical or different, independently selected from the group consisting of single bond, O, S, -SO 2 -、-SO-、-CR 1 R 2 -、-NR 3 -、-SiR 4 R 5 -、-SeR 6 R 7 -;
X 3 And X 4 Identical or different, independently selected from O, S, -SO 2 -、-SO-、-CR 8 R 9 -、-NR 10 -、-SiR 11 R 12 -、-SeR 13 R 14 -;
Ar 1 And Ar 2 The same or different, independently selected from any one of the following substituent groups:
wherein Ar is 3 、Ar 4 And Ar 5 Independently selected from substituted or unsubstituted C6-C60 aryl, and Ar 3 Is not phenyl;
X 5 selected from O, S, -NR 15 -、-CR 16 R 17 -;
R 1 -R 17 The same or different, independently selected from hydrogen, deuterium, cyano, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C60 heteroalkyl, substituted or unsubstituted C3-C60 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C5-C60 heteroaryl or bonded to adjacent atoms to form a ring;
denotes the attachment position of the substituent.
In some embodiments, in formula (1), X 3 And X 4 Same, and Ar 1 And Ar 2 The same is true.
In some embodiments, in formula (1), Ar 3 Is naphthyl.
In some embodiments, in formula (1), X 1 And X 2 Same, selected from O, S, -SO 2 -、-SO-、-CR 1 R 2 -、-NR 3 -、-SiR 4 R 5 -、-SeR 6 R 7 -, wherein R 1 -R 7 Independently selected from hydrogen, deuterium, cyano, methyl, phenyl, naphthyl, pyridyl or bonded to adjacent atoms to form a ring.
In some embodiments, in formula (1), X 1 And X 2 Different, X 1 Selected from single bond, O, S, -SO 2 -、-SO-、-CR 1 R 2 -、-NR 3 -、-SiR 4 R 5 -、-SeR 6 R 7 -,X 2 Selected from O, S, -SO 2 -、-SO-、-CR 1 R 2 -、-NR 3 -、-SiR 4 R 5 -、-SeR 6 R 7 -, wherein R 1 -R 7 Independently selected from hydrogen, deuterium, cyano, methyl, phenyl, naphthyl, pyridyl or bonded to adjacent atoms to form a ring.
In some embodiments, in formula (1), the organic compound is selected from any one of the following chemical structures:
the synthesis of the organic compound represented by the above formula (1) can be carried out using a known method. For example, a cross-coupling reaction of a transition metal such as nickel or palladium is used. Another synthesis method is C-C, C-N coupling reaction using transition metals such as magnesium or zinc. The above reaction is limited to mild reaction conditions and superior selectivity of various functional groups, and Suzuki and Buchwald reactions are preferred. The organic compound represented by the general formula (1) of the present invention may be used alone or in combination with other materials in an organic light-emitting device.
The organic electroluminescent device of the present invention is a light-emitting element comprising an organic compound represented by the general formula (1), the light-emitting element comprising a substrate, a first electrode, an organic layer, a second electrode and a covering layer, and a preferred device structure may comprise a substrate, a first electrode on the substrate, an organic layer on the first electrode, a second electrode on the organic layer and a covering layer on the outer side of the second electrode, the outer side of the second electrode in the present invention means a side away from the first electrode. The organic layer of the present invention may include a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, and an electron injection layer as the structure of the organic layer. The organic layer of the light-emitting element may have a single-layer structure, or may have a multilayer structure including a light-emitting layer, a hole-injecting layer, a hole-transporting layer, an electron-transporting layer, and an electron-injecting layer; while the organic layer may also comprise one or more layers, for example, the hole transport layer may comprise a first hole transport layer and a second hole transport layer. In the light-emitting element of the present invention, any material for the layer known in the art can be used for the layer other than the covering layer containing the organic compound of the present invention. In the light-emitting element of the present invention, the substrate material can be any substrate used in a typical organic light-emitting element, and can be soda glass, alkali-free glass, a transparent flexible substrate, an opaque material such as a silicon or stainless steel substrate, or a flexible polyimide film. Different substrate materials have different properties and different application directions.
The hole transport layer of the present invention can be formed by a method of stacking or mixing one or two or more kinds of hole transport materials, or a method of using a mixture of a hole transport material and a polymer binder. Since the hole transport material needs to transport holes from the positive electrode efficiently between electrodes to which an electric field is applied, it is desirable that the hole transport material has high hole injection efficiency and can transport injected holes efficiently. Therefore, a hole transport material is required to have an appropriate ionization potential, an appropriate energy level, and a large hole mobility, to be excellent in material stability, and to be less likely to generate impurities that become traps during manufacturing and use. The substance satisfying such conditions is not particularly limited, and examples thereof include carbazole derivatives, triarylamine derivatives, biphenyldiamine derivatives, fluorene derivatives, phthalocyanine compounds, hexacarbonitrile hexaazatriphenylene compounds, quinacridone compounds, perylene derivatives, anthraquinone compounds, F4-TCNQ, polyaniline, polythiophene, and polyvinylcarbazole, but are not limited thereto.
The light-emitting layer material of the present invention may include a host material (also referred to as a host material) and a dopant material (also referred to as a guest material), and the light-emitting layer material may include a plurality of host materials and a plurality of dopant materials. The light-emitting layer can be a single light-emitting layer or a composite light-emitting layer which is overlapped transversely or longitudinally. The dopant may be a fluorescent material or a phosphorescent material. The amount of the dopant is preferably 0.1 to 70% by mass, more preferably 0.1 to 30% by mass, still more preferably 1 to 30% by mass, yet more preferably 1 to 20% by mass, and particularly preferably 1 to 10% by mass. The fluorescent dopant material that can be used in the present invention may include: fused polycyclic aromatic derivatives, styrylamine derivatives, fused ring amine derivatives, boron-containing compounds, pyrrole derivatives, indole derivatives, carbazole derivatives, and the like, but are not limited thereto. Phosphorescent dopant materials useful in the present invention may include: heavy metal complexes, phosphorescent rare earth metal complexes, and the like, but are not limited thereto. Examples of the heavy metal complex include iridium complexes, platinum complexes, osmium complexes, and the like; examples of the rare earth metal complex include, but are not limited to, terbium complexes and europium complexes. Host materials useful in the present invention may include: host materials include fused aromatic ring derivatives, heterocyclic ring-containing compounds, and the like. Specifically, the fused aromatic ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene derivative, a fluoranthene derivative, and the like, and the heterocycle-containing compound includes a carbazole derivative, a dibenzofuran derivative, a dibenzothiophene derivative, a pyrimidine derivative, and the like, but is not limited thereto.
As the electron transport material of the present invention, a material having good electron mobility and suitable HOMO and LUMO energy levels are preferable. Electron transport materials that can be used in the present invention include: metal complexes, oxathiazole derivatives, oxazole derivatives, triazole derivatives, azabenzene derivatives, phenanthroline derivatives, diazene derivatives, silicon-containing heterocycles, boron-containing heterocycles, cyano compounds, quinoline derivatives, benzimidazole derivatives, and the like, but are not limited thereto.
The electron injection material of the present invention is preferably a substance having an ability to transport electrons, has an effect of injecting electrons from a cathode, and has an excellent ability to form a thin film. Electron injection materials that can be used as the present invention include: alkali metal compounds such as lithium oxide, lithium fluoride, lithium 8-hydroxyquinoline, lithium boron oxide, cesium carbonate, cesium 8-hydroxyquinoline, potassium silicate, calcium fluoride, calcium oxide, magnesium fluoride, magnesium oxide; a fluorenone; nitrogen-containing five-membered ring derivatives, for example, oxazole derivatives, oxadiazole derivatives, imidazole derivatives; a metal complex; anthraquinone dimethane, diphenoquinone, anthrone derivatives, and the like, but are not limited thereto, and these compounds may be used alone or in combination with other materials.
As the cathode material of the present invention, a material having a low work function is preferable in order to easily inject electrons into the organic layer. Cathode materials useful in the present invention include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, aluminum, silver, tin, lead, or alloys thereof; and multilayer materials, e.g. LiF/Al or LiO 2 and/Al, but not limited thereto. When the organic layer materials of the present invention are used, they may be formed into a single layer structure by film formation alone, or may be mixed with other materials to form a single layer structure, or may be formed into a single layer laminated structure by film formation alone, a single layer laminated structure by film mixing, a single layer formed by film formation alone, and a single layer laminated structure by film mixing, but not limited thereto.
The organic electroluminescent device of the present invention can be manufactured by sequentially stacking the above-described structures. The production method may employ a known method such as a dry film formation method or a wet film formation method. Specific examples of the dry film formation method include a vacuum deposition method, a sputtering method, a plasma method, an ion plating method, and the like. Specific examples of the wet film formation method include various coating methods such as a spin coating method, a dipping method, a casting method, and an ink jet method, but are not limited thereto. The organic light-emitting device can be widely applied to the fields of panel display, lighting sources, flexible OLEDs, electronic paper, organic solar cells, organic photoreceptors or organic thin film transistors, signs, signal lamps and the like. The fabrication of the above-described organic electroluminescent device is specifically described in the following examples. However, the following examples are given for illustrative purposes only, and the scope of the description is not limited thereto.
The organic compounds of the present invention are illustrated by the following examples, but are not limited to the organic compounds and synthetic methods illustrated in these examples. The solvent is purchased from Chinese medicines, and products such as common OLED raw materials, intermediates and the like are purchased from domestic OLED intermediate manufacturers; various palladium catalysts, ligands, etc. are available from noble platinum industries, Inc. 1 H-NMR data were measured using a JEOL (400MHz) nuclear magnetic resonance apparatus, and HPLC data were measured using a Shimadzu LC-20AD high performance liquid chromatograph. The materials used in the examples were:
example 1
Synthesis of Compound 1
To a reaction vessel under an argon atmosphere were added 32.6 g (100mmol) of the compound 1-A, 30.7 g (210mmol) of the compound 1-B, Pd (PPh) 3 ) 2 Cl 2 1.4 g (2mmol), 200ml (300mmol) of 1.5M aqueous sodium carbonate solution and 1000ml of ethylene glycol dimethyl ether (DME), and stirring overnight at 80 ℃. Cooling to room temperature, adding 800ml water, precipitating a large amount of solid, filtering,the filter cake was stirred with water for 3 times and dried under vacuum. The crude product was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane) to give 31.4 g of Compound 1-C in 85% yield and 99.5% HPLC purity.
To a reaction vessel were added, under an argon atmosphere, compound 1-C36.9G (100mmol), compound 1-D36.1G (210mmol), XPhos Pd G31.7G (2mmol),1.5M aqueous sodium carbonate solution 200ml (300mmol) and tetrahydrofuran 1000ml (THF), and the mixture was stirred under reflux overnight. Cooling to room temperature, adding 1500ml water, precipitating a large amount of solid, filtering, washing the filter cake with water for 3 times, and vacuum drying. The crude product was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane) to give 31.4 g of compound 1, 85% yield, 99.5% purity by HPLC.
1 HNMR(DMSO):δ8.46(s,2H),8.11(d,2H),8.00(d,2H),7.96(d,2H),7.93(d,2H),7.88(d,2H),7.83(s,2H),7.79(s,2H),7.61~7.59(m,4H),7.07(s,4H).
Example 2
Synthesis of Compound 5
The procedure of example 1 was repeated, except that the starting material was changed to 5-D.
1 HNMR(DMSO):δ8.03(m,2H),7.98(d,2H),7.88(d,2H),7.83(d,2H),7.82(d,2H),7.79(d,2H),7.76(s,2H),7.54(d,2H),7.39~7.31(m,4H),7.07(s,4H).
Example 3
Synthesis of Compound 18
The procedure of example 1 was repeated, except that the starting material was changed to 18-D.
1 HNMR(DMSO):δ7.88(d,2H),7.83(d,2H),7.79(d,2H),7.74(m,4H),7.38(d,4H),7.07(s,4H).
Example 4
Synthesis of Compound 37
The procedure of example 1 was repeated, except that the starting materials were changed to 37-A, 37-C and 37-D.
1 HNMR(DMSO):δ9.27(s,2H),8.85(d,2H),8.52(d,2H),8.15(d,2H),7.99(d,2H),7.92(d,2H),7.90(d,2H),7.75(s,4H),7.68(m,2H),7.63(m,2H),7.07(s,4H).
Example 5
Synthesis of Compound 44
The procedure was as in example 1 except that the starting materials were changed to 776-A and 776-B.
1 HNMR(DMSO):δ8.95(d,2H),8.50(d,2H),8.20(d,2H),8.12(s,2H),8.09(d,2H),7.99(d,2H),7.96(d,2H),7.92(d,2H),7.77(m,2H),7.52(m,4H),7.39(m,2H),7.25(d,4H),7.07(s,4H).
Example 6
Synthesis of Compound 63
The procedure of example 1 was repeated, except that the starting material was changed to 63-D.
1 HNMR(DMSO):δ9.51(s,2H),9.32(s,2H),8.52(d,2H),8.12(s,2H),7.99(d,2H),7.92(d,2H),7.84(s,2H),7.76(s,4H),7.63(d,2H),7.07(s,4H).
Example 7
Synthesis of Compound 73
The procedure of example 1 was repeated, except that the starting materials were changed to 73-A, 73-C and 73-D.
1 HNMR(DMSO):δ8.52(d,2H),8.31(d,2H),8.18(s,2H),8.15(d,2H),8.08(s,4H),8.07(d,2H),8.04(m,2H),7.92(d,2H),7.74(d,2H),7.70(d,2H),7.68(d,2H),7.07(s,4H).
Example 8
Synthesis of Compound 85
The procedure of example 1 was repeated, except that the starting materials were changed to 73-A, 85-B, 85-C and 85-D.
1 HNMR(DMSO):δ8.18(s,2H),8.07(d,4H),7.74(d,2H),7.68(d,2H),7.60(m,6H),7,30(s,4H),7.07(s,4H).
Example 9
Synthesis of Compound 90
The procedure of example 1 was repeated, except that the starting materials were changed to 73-A, 73-C and 90-D.
1 HNMR(DMSO):δ8.18(s,2H),7.96(d,2H),7.75(d,2H),7.74(d,2H),7.68(d,2H),7.49(m,4H),7.41(s,2H),7.25(m,12H),7.07(s,4H),
Example 10
Synthesis of Compound 112
The procedure of example 1 was repeated, except that the starting materials were changed to 112-A, 112-C and 112-D.
1 HNMR(DMSO):δ8.18(s,2H),8.09(d,2H),7.90(d,2H),7.89(s,2H),7.78(d,2H),7.74(d,2H),7.68(d,2H),7.55(d,2H),7.38(m,2H),7.28(m,2H),7.26(m,4H),7.18(m,2H),7.10(m,2H),7.07(s,4H).
Example 11
Synthesis of Compound 141
The procedure of example 1 was repeated, except that the starting materials were changed to 141-A and 141-C.
1 HNMR(DMSO):δ8.46(s,2H),8.18(s,2H),8.11(d,2H),8.00(d,1H),7.96(d,2H),7.93(d,2H),7.89(d,2H),7.74(d,2H),7.68(d,2H),7.61(m,2H),7.59(m,2H),7.45(d,2H),7.28(m,2H),7.27(m,2H),7.07(s,4H)
Example 12
Synthesis of Compound 176
The procedure was repeated as in example 1 except that the starting materials were changed to 176-A and 176-C.
1 HNMR(DMSO):δ8.46(s,2H),8.30(d,2H),8.13(d,2H),8.11(d,2H),8.00(d,2H),7.96(d,2H),7.93(d,2H),7.89(s,2H),7.62(m,2H),7.61(m,2H),7.59(m,2H),7.50(d,2H),7.07(s,4H).
Example 13
Synthesis of Compound 181
The procedure of example 1 was repeated, except that the starting materials were changed to 176-A, 176-C and 181-D.
1 HNMR(DMSO):δ8.45(d,2H),8.30(d,2H),8.24(d,2H),8.20(s,2H),8.13(d,2H),7.94(d,2H),7.93(d,2H),7.89(s,2H),7.62(m,2H),7.58(m,1H),7.56(m,2H),7.50(d,2H),7.49(m,2H),7.07(s,4H).
Example 14
Synthesis of Compound 194
The procedure of example 1 was repeated, except that the starting materials were changed to 176-A, 176-C and 194-D.
1 HNMR(DMSO):δ8.30(d,2H),8.13(d,2H),8.09(d,2H),8.06(d,2H),7.99(d,2H),7.96(d,4H),7.89(s,2H),7.63(m,2H),7.62(m,2H),7.58(s,1H),7.55(s,2H),7.50(d,2H),7.38(d,2H),7.25(d,4H),7.07(s,4H).
Example 15
Synthesis of Compound 228
The procedure of example 1 was repeated, except that the starting materials were changed to 228-A, 228-C and 228-D.
1 HNMR(DMSO):δ8.04(s,2H),7.97(d,2H),7.84(d,2H),7.74(m,4H),7.38(d,4H),7.07(s,4H).
Example 16
Synthesis of Compound 247
The procedure of example 1 was repeated, except that the starting materials were changed to 247-A, 247-C and 37-D.
1 HNMR(DMSO):δ9.27(s,2H),8.85(d,2H),8.52(d,2H),8.30(d,2H),8.15(d,2H),8.13(d,2H),8.03(d,3H),7.90(d,2H),7.89(s,2H),7.83(s,1H),7.75(s,4H),7.68(m,2H),7.63(m,2H),7.36(d,1H),7.07(s,4H).
Example 17
Synthesis of Compound 281
The procedure of example 1 was repeated, except that the starting materials were changed to 281-A and 281-C.
1 HNMR(DMSO):δ8.56(d,2H),8.46(s,2H),8.30(d,2H),8.11(d,2H),8.00(d,2H),7.96(d,2H),7.93(d,2H),7.89(s,2H),7.61(m,2H),7.59(m,2H),7.50(d,2H),7.07(s,4H).
Example 18
Synthesis of Compound 320
The procedure of example 1 was repeated, except that the starting materials were changed to 320-A, 320-C and 5-D.
1 HNMR(DMSO):δ8.03(d,2H),7.98(d,2H),7.82(d,2H),7.77(s,4H),7.54(d,2H),7.52(d,2H),7.39(m,2H),7.31(m,2H),7.18(d,2H),7.07(s,4H),1.69(s,6H).
Example 19
Synthesis of Compound 356
The procedure was repeated in the same manner as in example 1 except that the starting materials were changed to 356-A, 356-B and 181-D.
1 HNMR(DMSO):δ8.45(d,2H),8.24(d,2H),8.20(s,2H),7.94(d,2H),7.93(d,2H),7.56(m,2H),7.49(m,2H),7.34(d,2H),7.29(s,2H),7.15(d,2H),7.07(s,4H).
Example 20
Synthesis of Compound 403
The procedure of example 1 was repeated, except that the starting materials were changed to 403-A, 403-C and 18-D.
1 HNMR(DMSO):δ7.74(m,4H),7.38(d,4H),7.35(d,2H),7.33(d,2H),7.29(s,2H),7.24(m,2H),7.07(s,4H),7.08(d,2H),7.00(m,1H).
Example 21
Synthesis of Compound 425
The procedure of example 1 was repeated, except that the starting materials were changed to 425-A, 425-B, 425-C and 5-D.
1 HNMR(DMSO):δ8.03(d,2H),7.98(d,2H),7.82(d,2H),7.76(d,2H),7.60(s,2H),7.56(d,2H),7.54(d,2H),7.47(d,2H),7.31(m,2H),7.30(s,4H),1.69(s,4H).
Example 22
Synthesis of Compound 460
The procedure of example 1 was repeated, except that the starting materials were changed to 460-A, 460-C and 5-D.
1 HNMR(DMSO):δ8.03(d,2H),7.98(d,2H),7.82(d,2H),7.76(s,2H),7.54(d,2H),7.39(m,2H),7.37(m,2H),7.34(s,2H),7.31(d,4H),7.07(s,4H).
Example 23
Synthesis of Compound 509
The procedure of example 1 was repeated, except that the starting materials were changed to 509-A, 509-C and 194-D.
1 HNMR(DMSO):δ8.09(d,2H),8.06(d,2H),7.99(d,2H),7.96(d,4H),7.63(m,2H),7.60(m,2H),7.55(s,1H),7.39(d,2H),7.38(d,2H),7.33(d,2H),7.26(s,2H),7.25(d,4H),7.24(m,2H),7.07(s,4H),7.08(d,2H),7.00(m,1H).
Example 24
Synthesis of Compound 553
The procedure was as in example 18 except that the starting materials were changed to 553-A, 553-B, 553-C and 63-D.
1 HNMR(DMSO):δ9.51(s,2H),9.32(s,2H),8.52(d,2H),7.84(s,2H),7.76(s,4H),7.65(s,2H),7.63(d,2H),7.62(m,4H),7.58(m,2H),7.53(d,2H),7.50(d,4H),6.60(s,4H),1.69(s,12H).
Example 25
Synthesis of Compound 573
The procedure of example 1 was repeated, except that the starting materials were changed to 573-A, 425-B, 573-C and 18-D.
1 HNMR(DMSO):δ7.74(m,4H),7.71(s,2H),7.59(s,2H),7.38(d,4H),7.33(d,2H),7.24(m,4H),7.23(s,2H),7.08(d,4H),7.00(m,2H),6.65(d,2H).
Example 26
Synthesis of Compound 599
The procedure of example 1 was repeated, except that the starting materials were changed to 599-A, 599-C and 5-D.
1 HNMR(DMSO):δ8.15(s,2H),8.08(d,2H),8.03(d,2H),7.98(d,2H),7.87(d,2H),7.82(d,2H),7.76(d,2H),7.54(d,2H),7.39(m,2H),7.31(m,2H),7.07(s,4H).
Example 27
Synthesis of Compound 613
The procedure was as in example 1 except that the starting materials were changed to 613-A, 613-B, 613-C and 194-D.
1 HNMR(DMSO):δ8.12(s,2H),8.09(d,2H),8.06(d,2H),7.99(d,2H),7.90(d,2H),7.63(m,2H),7.61(d,2H),7.60(m,2H),7.59(d,4H),7.55(s,2H),7.53(d,4H),7.38(d,2H),7.04(s,4H).
Example 28
The manufacturing method of the film sample comprises the following specific steps: the alkali-free glass substrate was first subjected to UV ozone cleaning treatment for 20 minutes, and then placed in a vacuum evaporation apparatus, and then evacuated until the degree of vacuum in the apparatus reached 1X 10 -3 Under Pa, compound 1 was deposited by heating at a deposition rate of 0.1 nm/s by resistance heating deposition to prepare a thin film having a thickness of about 50 nm. The refractive index and attenuation coefficient of the prepared film sample are measured by an instrument which is an elliptical polarization spectrum (J.A. Woollam Co.Inc. M-2000) and has a color constant (the refractive index n is a decimal point 3-digit rounding).
Example 29
The procedure was as in example 28 except that compound 5 was used in place of compound 1. The organic light emitting device was evaluated and the results are shown in table 1.
Example 30
The procedure was as in example 28 except that compound 18 was used in place of compound 1. The organic light emitting device was evaluated and the results are shown in table 1.
Example 31
The reaction was conducted in the same manner as in example 28 except that the compound 37 was used instead of the compound 1. The organic light emitting device was evaluated and the results are shown in table 1.
Example 32
The procedure was as in example 28 except that compound 44 was used in place of compound 1. The organic light emitting device was evaluated. The evaluation results are shown in Table 1.
Example 33
The reaction was conducted in the same manner as in example 28 except that the compound 63 was used instead of the compound 1. The organic light emitting device was evaluated and the results are shown in table 1.
Example 34
The procedure was as in example 28 except that compound 73 was used in place of compound 1. The organic light emitting device was evaluated and the results are shown in table 1.
Example 35
The procedure was as in example 28 except that the compound 81 was used in place of the compound 1. The organic light emitting device was evaluated and the results are shown in table 1.
Example 36
The procedure was as in example 28 except that the compound 90 was used in place of the compound 1. The organic light emitting device was evaluated and the results are shown in table 1.
Example 37
The procedure was as in example 28 except that compound 112 was used instead of compound 1. The organic light emitting device was evaluated and the results are shown in table 1.
Example 38
The reaction was conducted in the same manner as in example 28 except that the compound 141 was used instead of the compound 1. The organic light emitting device was evaluated and the results are shown in table 1.
Example 39
The procedure was as in example 28 except that the compound 176 was used in place of the compound 1. The organic light emitting device was evaluated and the results are shown in table 1.
Example 40
The reaction was conducted in the same manner as in example 28 except that the compound 181 was used instead of the compound 1. The organic light emitting device was evaluated and the results are shown in table 1.
EXAMPLE 41
The reaction was conducted in the same manner as in example 28 except that the compound 194 was used instead of the compound 1. The organic light emitting device was evaluated. The evaluation results are shown in Table 1.
Example 42
The reaction was conducted in the same manner as in example 28 except that the compound 228 was used instead of the compound 1. The organic light emitting device was evaluated and the results are shown in table 1.
Example 43
The reaction was conducted in the same manner as in example 28 except that the compound 247 was used instead of the compound 1. The organic light emitting device was evaluated, and the evaluation results are shown in table 1.
Example 44
The reaction was conducted in the same manner as in example 28 except that the compound 281 was used instead of the compound 1. The organic light emitting device was evaluated and the results are shown in table 1.
Example 45
The procedure of example 28 was repeated, except that the compound 320 was used in place of the compound 1. The organic light emitting device was evaluated and the results are shown in table 1.
Example 46
The procedure was as in example 28 except that compound 356 was used instead of compound 1. The organic light emitting device was evaluated and the results are shown in table 1.
Example 47
The reaction was conducted in the same manner as in example 28 except that the compound 403 was used instead of the compound 1. The organic light emitting device was evaluated and the results are shown in table 1.
Example 48
The procedure was as in example 28 except that compound 425 was used in place of compound 1. The organic light emitting device was evaluated, and the results are shown in table 1.
Example 49
The same as in example 28 except that compound 460 was used instead of compound 1. The organic light emitting device was evaluated and the results are shown in table 1.
Example 50
The reaction was conducted in the same manner as in example 28 except that the compound 509 was used in place of the compound 1. The organic light emitting device was evaluated and the results are shown in table 1.
Example 51
The reaction was conducted in the same manner as in example 28 except that the compound 553 was used instead of the compound 1. The organic light emitting device was evaluated and the results are shown in table 1.
Example 52
The procedure was as in example 28 except for using compound 573 instead of compound 1. The organic light emitting device was evaluated and the results are shown in table 1.
Example 53
The procedure of example 28 was repeated, except that compound 599 was used instead of compound 1. The organic light emitting device was evaluated and the results are shown in table 1.
Example 54
The reaction was conducted in the same manner as in example 28 except that the compound 613 was used in place of the compound 1. The organic light emitting device was evaluated and the results are shown in table 1.
Comparative example 1
The procedure was as in example 28 except that SMD1 was used in place of Compound 1. The organic light emitting device was evaluated and the results are shown in table 1.
TABLE 1
As shown in table 1, the refractive index of the organic light emitting device using the organic compound of the present invention is greatly improved compared to SMD 1.
Example 55
The alkali-free glass was first washed with an ultrasonic cleaner using isopropyl alcohol for 15 minutes, and then subjected to UV ozone washing treatment in air for 30 minutes. The treated substrate was subjected to vacuum evaporation by first depositing aluminum 100 nm as an anode, and then depositing a hole injection layer (HATCN, 50 nm), a hole transport layer (NPD, 30 nm), a blue light emitting layer (host ADN and doped BD (weight ratio 95:5, 30 nm), an electron transport layer (Alq) on the anode 3 :Liq 3 1:1, 30 nm), an electron injection layer (LiF, 0.5 nm) was sequentially laminated and evaporated, and then Mg: Ag metal (weight ratio 10:1, 15 nm) was co-evaporated to prepare a semitransparent cathode. Compound 1(60 nm) was then evaporated as a capping layer. Finally atAnd encapsulating the light-emitting device by using an epoxy resin adhesive under the nitrogen atmosphere.
The test method of the light-emitting device comprises the following steps: the light-emitting device was tested for light-emitting properties of the sealing plate at room temperature in the atmosphere using a 10 milliampere per square meter direct current spectroradiometer (CS1000, konica minolta co., ltd.). The test gave a light-emitting efficiency of 7.4cd/a and a color purity CIE (x, y) ═ 0.139, 0.051, and a high-performance light-emitting element with high light-emitting efficiency and high color purity was obtained using compound 1 as a cover layer, and the test results are shown in table 2.
Example 56
The same members as those in example 55 were fabricated and evaluated except that the material of the cap layer was compound 5, and the test results were shown in Table 2.
Example 57
The same members as those in example 55 were fabricated and evaluated except that the material of the cover layer was compound 18, and the test results were shown in Table 2.
Example 58
The same members as those in example 55 were fabricated and evaluated except that the material of the cover layer was compound 37, and the test results were shown in Table 2.
Example 59
The same members as those in example 55 were fabricated and evaluated except that the material of the cover layer was compound 44, and the test results were shown in Table 2.
Example 60
The same members as those in example 55 were fabricated and evaluated except that the material of the cap layer was compound 63, and the test results were shown in Table 2.
Example 61
The same members as those in example 55 were fabricated and evaluated except that the material of the cover layer was compound 73, and the test results were shown in Table 2.
Example 62
The same members as those in example 55 were fabricated and evaluated except that the material of the cap layer was compound 81, and the test results were shown in Table 2.
Example 63
The same elements as those in example 55 were fabricated and evaluated except that the material of the covering layer was compound 90, and the test results are shown in Table 2.
Example 64
The same members as those in example 55 were fabricated and evaluated except that the material of the covering layer was compound 112, and the test results were shown in Table 2.
Example 65
The same members as those in example 55 were fabricated and evaluated except that the material of the cap layer was compound 141, and the test results were shown in Table 2.
Example 66
The same members as those in example 55 were fabricated and evaluated except that the material of the covering layer was compound 176, and the test results were shown in Table 2.
Example 67
The same members as those in example 55 were fabricated and evaluated except that the material of the cap layer was compound 181, and the test results were shown in table 2.
Example 68
The same elements as those in example 55 were fabricated and evaluated except that the material of the covering layer was compound 194, and the test results are shown in table 2.
Example 69
The same elements as those in example 55 were fabricated and evaluated except that the material of the cap layer was compound 228, and the results of the tests are shown in Table 2.
Example 70
The same elements as those in example 55 were fabricated and evaluated except that the material of the covering layer was compound 247, and the test results were shown in table 2.
Example 71
The same elements as those in example 55 were fabricated and evaluated except that the material of the cap layer was compound 281, and the results of the tests are shown in table 2.
Example 72
The same members as those in example 55 were fabricated and evaluated except that the material of the cap layer was compound 320, and the test results were shown in Table 2.
Example 73
The same members as those in example 55 were fabricated and evaluated except that the material of the covering layer was compound 356, and the test results were shown in Table 2.
Example 74
The same members as those in example 55 were fabricated and evaluated except that the material of the covering layer was compound 403, and the test results were shown in Table 2.
Example 75
The same members as those in example 55 were fabricated and evaluated except that the material of the covering layer was compound 425, and the test results were shown in Table 2.
Example 76
The same members as those in example 55 were fabricated and evaluated except that the material of the covering layer was compound 460, and the results of the tests are shown in Table 2.
Example 77
The same elements as those in example 55 were fabricated and evaluated except that the material of the cap layer was compound 509, and the test results were shown in table 2.
Example 78
The same elements as those in example 55 were fabricated and evaluated except that the material of the cap layer was compound 553, and the results of the tests are shown in Table 2.
Example 79
The same elements as those in example 55 were fabricated and evaluated except that the material of the cover layer was compound 573, and the test results are shown in Table 2.
Example 80
The same elements as those in example 55 were fabricated and evaluated except that the material of the cap layer was compound 599, and the test results were shown in table 2.
Example 81
The same members as those in example 55 were fabricated and evaluated except that the material of the cap layer was compound 613, and the test results are shown in Table 2.
Comparative example 2
The same members as those in example 55 were fabricated and evaluated except that the material of the cap layer was NPD, and the test results are shown in Table 2.
Comparative example 3
The same elements as those in example 55 were produced and evaluated except that the material of the cover layer was TBDB, and the evaluation results are shown in table 2.
TABLE 2
As shown in table 2, it can be seen that the organic compound of the present invention is used in an OLED light emitting device, and compared with comparative examples 2 and 3, the light extraction is significantly improved, and the device efficiency is improved under the same current density. Meanwhile, the efficiency of the OLED light-emitting device is improved, and the service life of the light-emitting device under the power consumption with the same brightness is also prolonged. In addition, the compound of the invention is used as a covering layer material to be applied to an OLED light-emitting device, can obtain a light-emitting device with high color purity, and is more suitable for industrial and commercial application.
The test results show that the compound is suitable for organic light-emitting device materials, can obtain light-emitting devices with high light-emitting efficiency and high color purity at the same time, and is more suitable for OLED light-emitting devices.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered as the technical solutions and the inventive concepts of the present invention within the technical scope of the present invention.
Claims (11)
1. An organic compound having a structure represented by the following formula (1):
in the formula (1), X 1 And X 2 Are identicalOr different, independently selected from the group consisting of single bond, O, S, -SO 2 -、-SO-、-CR 1 R 2 -、-NR 3 -、-SiR 4 R 5 -、-SeR 6 R 7 -;
X 3 And X 4 Identical or different, independently selected from O, S, -SO 2 -、-SO-、-CR 8 R 9 -、-NR 10 -、-SiR 11 R 12 -、-SeR 13 R 14 -;
Ar 1 And Ar 2 The same or different, independently selected from any one of the following substituent groups:
wherein Ar is 3 、Ar 4 And Ar 5 Independently selected from substituted or unsubstituted C6-C60 aryl, and Ar 3 Is not phenyl;
X 5 selected from O, S, -NR 15 -、-CR 16 R 17 -;
R 1 -R 17 The same or different, independently selected from hydrogen, deuterium, cyano, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C60 heteroalkyl, substituted or unsubstituted C3-C60 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C5-C60 heteroaryl or bonded to adjacent atoms to form a ring;
denotes the attachment position of the substituent.
2. An organic compound according to claim 1, wherein X is 3 And X 4 Same, and Ar 1 And Ar 2 The same is true.
3. The organic compound of claim 1, wherein Ar is Ar 3 Is naphthyl.
4. The organization of claim 1A compound characterized by X 1 And X 2 Same, selected from O, S, -SO 2 -、-SO-、-CR 1 R 2 -、-NR 3 -、-SiR 4 R 5 -、-SeR 6 R 7 -, wherein R 1 -R 7 Independently selected from hydrogen, deuterium, cyano, methyl, phenyl, naphthyl, pyridyl or bonded to adjacent atoms to form a ring.
5. An organic compound according to claim 1, wherein X is 1 And X 2 Different, X 1 Selected from single bond, O, S, -SO 2 -、-SO-、-CR 1 R 2 -、-NR 3 -、-SiR 4 R 5 -、-SeR 6 R 7 -,X 2 Selected from O, S, -SO 2 -、-SO-、-CR 1 R 2 -、-NR 3 -、-SiR 4 R 5 -、-SeR 6 R 7 -, wherein R 1 -R 7 Independently selected from hydrogen, deuterium, cyano, methyl, phenyl, naphthyl, pyridyl or bonded to adjacent atoms to form a ring.
7. an organic material comprising one or more of the organic compounds of any one of claims 1-6.
8. An organic light-emitting device comprising one or more of the organic compounds of any one of claims 1 to 6, or the organic material of claim 7.
9. The organic light emitting device according to claim 8,
comprises a substrate, a first electrode, one or more organic layers including a light-emitting layer, and a second electrode element;
further comprising a cover layer comprising one or more of the organic compounds of any of claims 1 to 6 or the organic material of claim 7.
10. The organic light-emitting device according to claim 8 or 9, wherein the organic light-emitting device comprises an organic photovoltaic device, an organic electroluminescent device, an organic solar cell, electronic paper, an organic photoreceptor, or an organic thin film transistor.
11. Display or lighting device, characterized in that it comprises an organic light emitting device according to any one of claims 8 to 10.
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