CN113519073A - Organic light emitting device - Google Patents
Organic light emitting device Download PDFInfo
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- CN113519073A CN113519073A CN202080015506.3A CN202080015506A CN113519073A CN 113519073 A CN113519073 A CN 113519073A CN 202080015506 A CN202080015506 A CN 202080015506A CN 113519073 A CN113519073 A CN 113519073A
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- 150000001875 compounds Chemical class 0.000 claims description 457
- -1 (phenyl) naphthyl Chemical group 0.000 claims description 143
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- 229910052805 deuterium Inorganic materials 0.000 claims description 21
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 12
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- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 7
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- 239000010405 anode material Substances 0.000 description 4
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- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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- 229910052749 magnesium Inorganic materials 0.000 description 1
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- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
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- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
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- 125000001425 triazolyl group Chemical group 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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Abstract
The present disclosure relates to an organic light emitting device having improved driving voltage, efficiency, and lifetime.
Description
Technical Field
Cross Reference to Related Applications
This application claims the benefit of the filing date of korean patent application No. 10-2019-0143630, filed on 11.11.2019 to the korean intellectual property office, and the filing date of korean patent application No. 10-2020-0150222, filed on 11.11.2020 to the korean intellectual property office, the entire contents of which are incorporated herein by reference.
The present disclosure relates to an organic light emitting device having improved driving voltage, efficiency, and lifetime.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy by using an organic material. An organic light emitting device using an organic light emitting phenomenon has characteristics such as a wide viewing angle, excellent contrast, a fast response time, excellent brightness, a driving voltage, and a response speed, and thus many studies have been made.
An organic light emitting device generally has a structure including an anode, a cathode, and an organic material layer interposed between the anode and the cathode. The organic material layer generally has a multi-layer structure including different materials to improve efficiency and stability of the organic light emitting device, and for example, the organic material layer may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of the organic light emitting device, if a voltage is applied between two electrodes, holes are injected from an anode into an organic material layer and electrons are injected from a cathode into the organic material layer, and excitons are formed when the injected holes and electrons meet each other, and light is emitted when the excitons fall to a ground state again.
Among the organic light emitting devices as described above, there is a continuous need to develop organic light emitting devices having improved driving voltage, efficiency, and lifetime.
[ Prior art documents ]
[ patent document ]
(patent document 0001) Korean unexamined patent publication No. 10-2000-0051826
Disclosure of Invention
Technical problem
The present disclosure relates to an organic light emitting device having improved driving voltage, efficiency, and lifetime.
Technical scheme
The following organic light emitting devices are provided herein:
an organic light-emitting device is provided,
the method comprises the following steps:
an anode, a cathode, and a light-emitting layer between the anode and the cathode.
Wherein the light emitting layer includes a compound represented by the following chemical formula 1 and a compound represented by the following chemical formula 2:
[ chemical formula 1]
In the chemical formula 1, the first and second,
x is O or S, and X is O or S,
each Y is independently N or CH, provided that at least one Y is N,
L1is a single bond, or substituted or unsubstituted C6-60An arylene group, a cyclic or cyclic alkylene group,
Ar1and Ar2Each independently is substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O and S2-60(ii) a heteroaryl group, wherein,
[ chemical formula 2]
In the chemical formula 2, the first and second organic solvents,
L2is substituted or unsubstituted C6-60An arylene group, a cyclic or cyclic alkylene group,
L3and L4Each independently a single bond, or a substituted or unsubstituted C6-60An arylene group, a cyclic or cyclic alkylene group,
Ar3and Ar4Each independently is substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O and S2-60(ii) a heteroaryl group, wherein,
r is hydrogen, deuterium, or substituted or unsubstituted C6-60Aryl, and
n is an integer of 0 to 9.
Advantageous effects
The organic light emitting device described above has excellent driving voltage, efficiency, and lifetime by including the compound represented by chemical formula 1 and the compound represented by chemical formula 2 in the light emitting layer.
Drawings
Fig. 1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
Fig. 2 shows an example of an organic light emitting device including a substrate 1, an anode 2, a hole transport layer 5, a light emitting layer 3, an electron transport layer 6, and a cathode 4.
Detailed Description
Hereinafter, embodiments of the present disclosure will be described in more detail to facilitate understanding of the present invention.
As used herein, a symbol
Or
Meaning a bond to another substituent.
As used herein, the term "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthio group; an arylthio group; an alkylsulfonyl group; an arylsulfonyl group; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamino group; an aralkylamino group; a heteroaryl amino group; an arylamine group; an aryl phosphine group; or a heteroaryl group comprising at least one of N, O and S atoms, or a substituent that is unsubstituted or linked by two or more of the substituents exemplified above. For example, "a substituent to which two or more substituents are attached" may be a biphenyl group. That is, biphenyl can be an aryl group, or it can also be interpreted as a substituent with two phenyl groups attached.
In the present disclosure, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the carbonyl group may be a compound having the following structural formula, but is not limited thereto.
In the present disclosure, the ester group may have a structure in which the oxygen of the ester group may be substituted with a linear, branched, or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the ester group may be a compound having the following structural formula, but is not limited thereto.
In the present disclosure, the carbon number of the imide group is not particularly limited, but is preferably 1 to 25.
Specifically, the imide group may be a compound having the following structural formula, but is not limited thereto.
In the present disclosure, the silyl group specifically includes, but is not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like.
In the present disclosure, the boron group specifically includes a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group, but is not limited thereto.
In the present disclosure, examples of halogen groups include fluorine, chlorine, bromine, or iodine.
In the present disclosure, the alkyl group may be linear or branched, and the carbon number thereof is not particularly limited, but is preferably 1 to 40. According to one embodiment, the carbon number of the alkyl group is from 1 to 20. According to another embodiment, the carbon number of the alkyl group is from 1 to 10. According to another embodiment, the carbon number of the alkyl group is 1 to 6. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, n-butyl, 1-ethyl-butyl, pentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3, 2-dimethylbutyl, heptyl, 1-methylhexyl, cyclohexyl, octyl, 1-methyl-pentyl, 2-pentyl, and the like, Isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.
In the present disclosure, the alkenyl group may be linear or branched, and the carbon number thereof is not particularly limited, but is preferably 2 to 40. According to one embodiment, the carbon number of the alkenyl group is 2 to 20. According to another embodiment, the carbon number of the alkenyl group is 2 to 10. According to yet another embodiment, the carbon number of the alkenyl group is 2 to 6. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-diphenylvinyl-1-yl, 2-phenyl-2- (naphthyl-1-yl) vinyl-1-yl, 2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl, styryl and the like, but are not limited thereto.
In the present disclosure, the cycloalkyl group is not particularly limited, but the carbon number thereof is preferably 3 to 60. According to one embodiment, the carbon number of the cycloalkyl group is from 3 to 30. According to another embodiment, the carbon number of the cycloalkyl group is from 3 to 20. According to yet another embodiment, the carbon number of the cycloalkyl group is from 3 to 6. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.
In the present disclosure, the aryl group is not particularly limited, but its carbon number is preferably 6 to 60, and it may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is from 6 to 30. According to one embodiment, the carbon number of the aryl group is from 6 to 20. As the monocyclic aryl group, the aryl group may be phenyl, biphenyl, terphenyl, etc., but is not limited thereto. The polycyclic aryl groups include naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl,
A phenyl group, a fluorenyl group, and the like, but are not limited thereto.
In the present disclosure, the fluorenyl group may be substituted, and two substituents may be connected to each other to form a spiro ring structure. In the case of the fluorenyl group being substituted, it can form
And the like. However, the structure is not limited thereto.
In the present disclosure, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si and S as a heteroatom, and the carbon number thereof is not particularly limited, but is preferably 2 to 60. Examples of heterocyclic groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,
Azolyl group,
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinyl
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl, isoquinoyl
Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but is not limited thereto.
In the present disclosure, the aryl group of the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aforementioned aryl group. In the present disclosure, the alkyl groups in the aralkyl, alkylaryl, and alkylamino groups are the same as the examples of the aforementioned alkyl groups. In the present disclosure, the heteroaryl group in the heteroarylamine may be used as described for the heterocyclic group described above. In the present disclosure, the alkenyl group in the aralkenyl group is the same as the example of the aforementioned alkenyl group. In the present disclosure, the description of the aforementioned aryl groups may be applied, except that the arylene group is a divalent group. In the present disclosure, the foregoing description of heteroaryl may apply, except that heteroarylene is a divalent group. In the present disclosure, the description of the aforementioned aryl or cycloalkyl groups may be applied, except that the hydrocarbon ring is not a monovalent group but is formed by combining two substituents. In the disclosure, the description of the aforementioned heterocyclic group may be applied except that the heterocyclic group is not a monovalent group but is formed by combining two substituents.
Hereinafter, the present disclosure will be described in detail for each configuration.
An anode and a cathode
The anode and the cathode used in the present disclosure mean electrodes used in an organic light emitting device.
As the anode material, it is generally preferable to use a material having a large work function so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material include: metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combinations of metals and oxides, e.g. ZnO: Al or SNO2Sb; conducting polymers, e.g. poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDOT), polypyrrole and polyaniline; and the like, but are not limited thereto.
As the cathode material, it is generally preferable to use a material having a small work function so that electrons can be easily injected into the organic material layer. Specific examples of the cathode material include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; materials of multilayer construction, e.g. LiF/Al or LiO2Al; and the like, but are not limited thereto.
Hole injection layer
The organic light emitting device according to the present disclosure may further include a hole injection layer on the anode, if necessary.
The hole injection layer is a layer that injects holes from the electrode, and the hole injection material is preferably a compound of: which has the ability to transport holes, the effect of injecting holes in the anode, and an excellent hole injection effect to the light emitting layer or the light emitting material, prevents excitons generated in the light emitting layer from moving to the electron injecting layer or the electron injecting material, and has an excellent thin film forming ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting material is between the work function of the anode material and the HOMO of the surrounding organic material layer.
Specific examples of the hole injection material include metalloporphyrin, oligothiophene, arylamine-based organic material, hexanenitrile-hexaazatriphenylene-based organic material, quinacridone-based organic material, perylene-based organic material, anthraquinone-based, polyaniline-based, polythiophene-based conductive polymer, and the like, but are not limited thereto.
Hole transport layer
The organic light emitting device according to the present disclosure may include a hole transport layer on the anode (or on the hole injection layer when present), if necessary.
The hole transport layer is a layer that receives holes from the anode or the hole injection layer and transports the holes to the light emitting layer. The hole transport material is suitably a material having a large hole mobility, which can receive holes from the anode or the hole injection layer and transport the holes to the light emitting layer.
Specific examples of the hole transport material include arylamine-based organic materials, conductive polymers, block copolymers in which both a conjugated portion and a non-conjugated portion exist, and the like, but are not limited thereto.
Luminescent layer
The light-emitting layer used in the present disclosure means a layer that can emit light in the visible light region by combining holes and electrons transported from the anode and the cathode. In general, the light emitting layer includes a host material and a dopant material, and in the present disclosure, a compound represented by chemical formula 1 and a compound represented by chemical formula 2 are included as hosts.
In chemical formula 1, preferably, all Y are N.
Preferably, L1Is a single bond, phenylene or naphthylene. More preferably, L1Is a single bond,
Or
Preferably, Ar1And Ar2Each independently is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, (phenyl) naphthyl, (naphthyl) phenyl, dimethylfluorenyl, diphenylfluorenyl, dibenzofuranyl, dibenzothienyl, carbazol-9-yl, 9-phenyl-9H-carbazolyl, Ar1And Ar2Each independently unsubstituted or substituted with at least one deuterium. When Ar is1Or Ar2When substituted with at least one deuterium, preferably they are each selected from any one of the following:
preferably, Ar1Is phenyl, biphenyl or naphthyl, Ar1Unsubstituted or substituted with at least one deuterium; and Ar2Is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, (phenyl) naphthyl, (naphthyl) phenyl, dimethylfluorenyl, diphenylfluorenyl, dibenzofuranyl, dibenzothienyl, carbazol-9-yl, 9-phenyl-9H-carbazolyl, Ar2Unsubstituted or substituted with at least one deuterium.
Representative examples of the compound represented by chemical formula 1 are as follows:
also provided herein is a method for preparing a compound represented by chemical formula 1 as shown in the following reaction scheme 1.
[ reaction scheme 1]
In reaction scheme 1, the definition of the remaining substituents other than X 'is the same as defined above, and X' is halogen, preferably bromine or chlorine. The above reaction is a Suzuki coupling reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups used for the Suzuki coupling reaction may be modified as known in the art. The above preparation method can be further presented in the preparation examples described below.
In chemical formula 2, preferably, chemical formula 2 is represented by the following chemical formula 2-1:
[ chemical formula 2-1]
Wherein in the chemical formula 2-1,
R1is hydrogen, deuterium or phenyl,
n1 is an integer from 0 to 8,
L2、L3、L4、Ar3、Ar4and R is as defined above.
Preferably, L2Is phenylene or phenylene substituted with at least one deuterium. By at least one deuterium extractionThe substituted phenylene group is preferably selected from any one of the following:
preferably, L3And L4Each independently of the other being a single bond, phenylene, biphenyldiyl or naphthylene, L3And L4Each independently unsubstituted or substituted with at least one deuterium. When L is3Or L4When substituted with at least one deuterium, preferably they are each selected from any one of the following:
preferably, Ar3And Ar4Each independently of the others is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, (phenyl) phenanthryl, triphenylene, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, diphenylfluorenyl, dibenzofuranyl, (phenyl) dibenzofuranyl, dibenzothienyl, (phenyl) dibenzothienyl, carbazol-9-yl or 9-phenyl-9H-carbazolyl, Ar3And Ar4Each independently unsubstituted or substituted with at least one deuterium. When Ar is3Or Ar4When substituted with at least one deuterium, each is preferably selected from any one of the following:
representative examples of the compound represented by chemical formula 2 are as follows:
also provided herein is a method for preparing a compound represented by chemical formula 2 as shown in the following reaction scheme 2.
[ reaction scheme 2]
Wherein in reaction scheme 2, the definition of the remaining substituents other than X 'is the same as defined above, and X' is halogen, preferably bromine or chlorine. The above reaction is an amine substitution reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups for the amine substitution reaction may be modified as known in the art. The above preparation method can be further presented in the preparation examples described below.
Preferably, in the light emitting layer, the weight ratio of the compound represented by chemical formula 1 to the compound represented by chemical formula 2 is 10:90 to 90:10, more preferably 20:80 to 80:20, 30:70 to 70:30, or 40:60 to 60: 40.
Meanwhile, the light emitting layer may include a dopant in addition to the host. The dopant material is not particularly limited as long as it is a material for an organic light emitting device. As examples, aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like can be mentioned. Specific examples of the aromatic amine derivative includeSubstituted or unsubstituted fused aromatic ring derivatives having an arylamino group, examples of which include pyrene, anthracene, having an arylamino group,
And diindenopyrene, and the like. The styrylamine compound is a compound in which at least one arylvinyl group is substituted in a substituted or unsubstituted arylamine, wherein one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group are substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styrenediamine, styrenetriamine, styrenetetramine, and the like. Further, examples of the metal complex include iridium complexes, platinum complexes, and the like, but are not limited thereto.
Electron transport layer
The organic light emitting device according to the present disclosure may include an electron transport layer on the light emitting layer, if necessary.
The electron transport layer is a layer that receives electrons from the cathode or an electron injection layer formed on the cathode and transports the electrons to the light-emitting layer, and suppresses transfer of holes from the light-emitting layer, and the electron transport material is suitably a material that: it can well receive electrons from the cathode and transfer the electrons to the light emitting layer, and has a large electron mobility.
Specific examples of the electron transport material include: al complexes of 8-hydroxyquinoline; comprising Alq3The complex of (1); an organic radical compound; a hydroxyflavone-metal complex; and the like, but are not limited thereto. The electron transport layer may be used with any desired cathode material as used according to conventional techniques. Suitable examples of cathode materials are, in particular, typical materials having a low work function, followed by an aluminum or silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum or silver layer.
Electron injection layer
The organic light emitting device according to the present disclosure may further include an electron injection layer on the light emitting layer (or on the electron transport layer, if present) if necessary.
The electron injection layer is a layer that injects electrons from the electrode, and is preferably a compound of: it has an ability to transport electrons, has an effect of injecting electrons from a cathode and an excellent effect of injecting electrons into a light emitting layer or a light emitting material, prevents excitons generated from the light emitting layer from moving to a hole injection layer, and is also excellent in an ability to form a thin film.
Specific examples of materials that can be used as the electron-injecting layer include fluorenones, anthraquinone dimethanes, diphenoquinones, thiopyran dioxides, fluorine-containing compounds, and fluorine-containing compounds,
Azole,
Oxadiazole, triazole, imidazole, tetracarboxylic acid, fluorenylidene methane, anthrone, etc., and derivatives thereof, metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.
Examples of the metal complex compounds include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), gallium tris (8-quinolinolato), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), chlorogallium bis (2-methyl-8-quinolinolato), gallium bis (2-methyl-8-quinolino) (o-cresol), aluminum bis (2-methyl-8-quinolino) (1-naphthol), gallium bis (2-methyl-8-quinolino) (2-naphthol), and the like, but are not limited thereto.
Organic light emitting device
Fig. 1 and 2 illustrate the structure of an organic light emitting device according to the present disclosure. Fig. 1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. Fig. 2 shows an example of an organic light emitting device including a substrate 1, an anode 2, a hole transport layer 5, a light emitting layer 3, an electron transport layer 6, and a cathode 4.
The organic light emitting device according to the present disclosure may be manufactured by sequentially stacking the above-described structures. In this case, the organic light emitting device may be manufactured by: the anode is formed by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate using a PVD (physical vapor deposition) method such as a sputtering method or an electron beam evaporation method, forming the above-described layers on the anode, and then depositing a material that can be used as a cathode thereon. In addition to such a method, an organic light emitting device may be manufactured by sequentially depositing from a cathode material to an anode material on a substrate in the reverse order of the above-described configuration (WO 2003/012890). In addition, the light emitting layer may be formed by subjecting the host and the dopant to a vacuum deposition method and a solution coating method. Herein, the solution coating method means spin coating, dip coating, doctor blade coating, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
On the other hand, the organic light emitting device according to the present disclosure may be a front side emission type, a rear side emission type, or a double side emission type, depending on the material used.
The preparation of an organic light emitting device including the compound represented by chemical formula 1 and the compound represented by chemical formula 2 will be described in detail in the following examples. However, these examples are given for illustrative purposes only and are not intended to limit the scope of the present disclosure.
[ preparation examples ]
Preparation examples 1 to 1
Compound sub1(15g, 40.8mmol) and compound a (11.8g, 44.9mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (16.9g, 122.3mmol) was dissolved in water (51ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.4 mmol). After 9 hours of reaction, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred andfiltration was carried out, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 1(14.6 g). (yield: 65%, MS: [ M + H ]]+＝550)
Preparation examples 1 to 2
Compound sub2(15g, 47.2mmol) and compound a (13.6g, 51.9mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (19.6g, 141.6mmol) was dissolved in water (59ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.5 mmol). After reacting for 10 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 2(14.4 g). (yield: 61%, MS: [ M + H ]]+＝500)
Preparation examples 1 to 3
Compound sub3(15g, 38.1mmol) and compound a (11g, 41.9mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (15.8g, 114.3mmol) was dissolved in water (47ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.4 mmol). After 9 hours of reaction, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was reduced under reduced pressureAnd (5) distilling. The concentrated compound was purified by silica gel column chromatography to give compound 3(13.4 g). (yield: 61%, MS: [ M + H ]]+＝576)
Preparation examples 1 to 4
Compound sub4(15g, 43.6mmol) and compound a (12.6g, 48mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (18.1g, 130.9mmol) was dissolved in water (54ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.4 mmol). After 9 hours of reaction, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 4(18.3 g). (yield: 80%, MS: [ M + H ]]+＝526)
Preparation examples 1 to 5
Compound sub5(15g, 35.7mmol) and compound a (10.3g, 39.3mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (14.8g, 107.2mmol) was dissolved in water (44ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.4 mmol). After reacting for 8 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. Passing the concentrated compound throughPurification by silica gel column chromatography gave compound 5(15.2 g). (yield: 71%, MS: [ M + H ]]+＝602)
Preparation examples 1 to 6
Compound sub6(15g, 35.9mmol) and compound a (10.3g, 39.5mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (14.9g, 107.7mmol) was dissolved in water (45ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.4 mmol). After reacting for 12 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 6(13.1 g). (yield: 61%, MS: [ M + H ]]+＝600)
Preparation examples 1 to 7
Compound sub7(15g, 35.7mmol) and compound a (10.3g, 39.3mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (14.8g, 107.2mmol) was dissolved in water (44ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.4 mmol). After reacting for 8 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. Purifying the concentrated compound by silica gel column chromatography to obtainCompound 7(14.2 g). (yield: 66%, MS: [ M + H ]]+＝602)
Preparation examples 1 to 8
Compound sub8(15g, 40.8mmol) and compound a (11.8g, 44.9mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (16.9g, 122.3mmol) was dissolved in water (51ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.4 mmol). After reacting for 12 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 8(13.4 g). (yield: 60%, MS: [ M + H ]]+＝550)
Preparation examples 1 to 9
Compound sub9(15g, 40.8mmol) and compound a (11.8g, 44.9mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (16.9g, 122.3mmol) was dissolved in water (51ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.4 mmol). After reacting for 12 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 9(14.1 g). (yield:63％，MS：[M+H]+＝550)
preparation examples 1 to 10
Compound sub10(15g, 38.1mmol) and compound a (11g, 41.9mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (15.8g, 114.3mmol) was dissolved in water (47ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.4 mmol). After reacting for 8 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 10(15.8 g). (yield: 72%, MS: [ M + H ]]+＝576)
Preparation examples 1 to 11
Compound sub11(15g, 38.1mmol) and compound a (11g, 41.9mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (15.8g, 114.3mmol) was dissolved in water (47ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.4 mmol). After reacting for 8 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 11(16.6 g). (yield: 76%, MS: [ M + H ]]+＝576)
Preparation examples 1 to 12
Compound sub12(15g, 41.9mmol) and compound a (12.1g, 46.1mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (17.4g, 125.8mmol) was dissolved in water (52ml), added to the mixture, and the mixture was stirred well, followed by the addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.4 mmol). After reacting for 12 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 12(13.8 g). (yield: 61%, MS: [ M + H ]]+＝540)
Preparation examples 1 to 13
Compound sub13(15g, 41.9mmol) and compound a (12.1g, 46.1mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (17.4g, 125.8mmol) was dissolved in water (52ml), added to the mixture, and the mixture was stirred well, followed by the addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.4 mmol). After 9 hours of reaction, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 13(15.4 g). (yield: 68%, MS: [ M + H ]]+＝540)
Preparation examples 1 to 14
Compound sub14(15g, 36.8mmol) and compound a (10.6g, 40.5mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (15.2g, 110.3mmol) was dissolved in water (46ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.4 mmol). After reacting for 11 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 14(16.3 g). (yield: 75%, MS: [ M + H ]]+＝590)
Preparation examples 1 to 15
Compound sub15(15g, 36.8mmol) and compound a (10.6g, 40.5mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (15.2g, 110.3mmol) was dissolved in water (46ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.4 mmol). After reacting for 12 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 15(15.2 g). (yield: 70%, MS: [ M + H ]]+＝590)
Preparation examples 1 to 16
Compound sub16(15g, 40.1mmol) and compound a (11.6g, 44.1mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (16.6g, 120.4mmol) was dissolved in water (50ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.4 mmol). After reacting for 12 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 16(13.8 g). (yield: 62%, MS: [ M + H ]]+＝556)
Preparation examples 1 to 17
Compound sub17(15g, 40.1mmol) and compound a (11.6g, 44.1mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (16.6g, 120.4mmol) was dissolved in water (50ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.4 mmol). After 9 hours of reaction, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 17(15.1 g). (yield: 68%, MS: [ M + H ]]+＝556)
Preparation examples 1 to 18
Compound sub18(15g, 40.1mmol) and compound a (11.6g, 44.1mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (16.6g, 120.4mmol) was dissolved in water (50ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.4 mmol). After 9 hours of reaction, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 18(17.8 g). (yield: 80%, MS: [ M + H ]]+＝556)
Preparation examples 1 to 19
Compound sub19(15g, 34.6mmol) and compound a (10g, 38.1mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (14.4g, 103.9mmol) was dissolved in water (43ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.3 mmol). After reacting for 10 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 19(15.5 g). (yield: 73%, MS: [ M + H ]]+＝615)
Preparation examples 1 to 20
Compound sub20(15g, 34.6mmol) and compound a (10g, 38.1mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (14.4g, 103.9mmol) was dissolved in water (43ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.3 mmol). After reacting for 11 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 20(17 g). (yield: 80%, MS: [ M + H ]]+＝61)
Preparation examples 1 to 21
Compound sub21(15g, 42mmol) and compound a (12.1g, 46.2mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (17.4g, 126.1mmol) was dissolved in water (52ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.4 mmol). After 9 hours of reaction, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 21(14.5 g). (yield: 64%, MS: [ M + H ]]+＝539)
Preparation examples 1 to 22
Compound sub22(15g, 31.1mmol) and compound a (9g, 34.2mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (12.9g, 93.2mmol) was dissolved in water (39ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.3 mmol). After reacting for 11 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 22(12.4 g). (yield: 60%, MS: [ M + H ]]+＝665)
Preparation examples 1 to 23
Compound sub2(15g, 47.2mmol) and compound B (7.4g, 47.2mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (19.6g, 141.6mmol) was dissolved in water (59ml), added to the mixture, and the mixture was stirred well, followed by the addition of tetrakis (triphenylphosphine) palladium (0) (0.5g, 0.5 mmol). After reacting for 10 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound subB-1(13.9 g). (yield: 75%, MS: [ M + H ]]+＝394)
Compound subB-1(15g, 38.1mmol) and Compound A (11g, 41.9mmol) were added to THF (300ml) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (15.8g, 114.3mmol) was dissolved in water (47ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.4 mmol). After reacting for 12 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 23(15.3 g). (yield: 70%, MS: [ M + H ]]+＝576)
Preparation examples 1 to 24
Compound sub23(15g, 35.7mmol) and compound B (5.6g, 35.7mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (14.8g, 107.2mmol) was dissolved in water (44ml), added to the mixture, and the mixture was stirred well, followed by the addition of tetrakis (triphenylphosphine) palladium (0) (0.4g, 0.4 mmol). After reacting for 12 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound subB-2(12 g). (yield: 68%, MS: [ M + H ]]+＝496)
Compound subB-2(15g, 30.2mmol) and Compound A (8.7g, 33.3mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (12.5g, 90.7mmol) was dissolved in water (38ml), added to the mixture, and the mixture was stirred well, followed by the addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.3 mmol). After reacting for 8 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 24(13.1 g). (yield: 64%, MS: [ M + H ]]+＝678)
Preparation examples 1 to 25
Compound sub12(15g, 41.9mmol) and compound B (6.6g, 41.9mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (17.4g, 125.8mmol) was dissolved in water (52ml), added to the mixture, and the mixture was stirred well, followed by the addition of tetrakis (triphenylphosphine) palladium (0) (0.5g, 0.4 mmol). After reacting for 10 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound subB-3(12.9 g). (yield: 71%, MS: [ M + H ]]+＝434)
Compound subB-3(15g, 34.6mmol) and Compound A (10g, 38 mmol) were placed under a nitrogen atmospherel) was added to THF (300ml) and the mixture was stirred and refluxed. Then, potassium carbonate (14.3g, 103.7mmol) was dissolved in water (43ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.3 mmol). After reacting for 12 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 25(17 g). (yield: 80%, MS: [ M + H ]]+＝616)
Preparation examples 1 to 26
Compound sub17(15g, 40.1mmol) and compound B (6.3g, 40.1mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (16.6g, 120.4mmol) was dissolved in water (50ml), added to the mixture, and the mixture was stirred well, followed by the addition of tetrakis (triphenylphosphine) palladium (0) (0.5g, 0.4 mmol). After reacting for 11 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound subB-4(12.1 g). (yield: 67%, MS: [ M + H ]]+＝450)
Compound subB-4(15g, 33.3mmol) and Compound A (9.6g, 36.7mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, the carbon is mixedPotassium (13.8g, 100mmol) was dissolved in water (41ml), added to the mixture, and the mixture was stirred well before bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was added. After reacting for 11 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 26(15.8 g). (yield: 75%, MS: [ M + H ]]+＝632)
Preparation examples 1 to 27
Compound sub3(15g, 38.1mmol) and compound B (10g, 38.1mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (15.8g, 114.3mmol) was dissolved in water (47ml), added to the mixture, and the mixture was stirred well, followed by the addition of tetrakis (triphenylphosphine) palladium (0) (0.4g, 0.4 mmol). After reacting for 8 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound subB-5(14.1 g). (yield: 79%, MS: [ M + H ]]+＝470)
Compound subB-5(15g, 31.9mmol) and Compound A (9.2g, 35.1mmol) were added to THF (300ml) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (13.2g, 95.8mmol) was dissolved in water (40ml), added to the mixture, andthe mixture was stirred well and then bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was added. After reacting for 10 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 27(12.5 g). (yield: 60%, MS: [ M + H ]]+＝652)
Preparation examples 1 to 28
Compound sub24(15g, 35.4mmol) and compound B (5.5g, 35.4mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (14.7g, 106.2mmol) was dissolved in water (44ml), added to the mixture, and the mixture was stirred well, followed by the addition of tetrakis (triphenylphosphine) palladium (0) (0.4g, 0.4 mmol). After 9 hours of reaction, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound subB-6(12.5 g). (yield: 71%, MS: [ M + H ]]+＝500)
Compound subB-6(15g, 30mmol) and Compound A (8.6g, 33mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (12.4g, 90mmol) was dissolved in water (37ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.3 mmol).After reacting for 12 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 23(14.9 g). (yield: 73%, MS: [ M + H ]]+＝682)
Preparation examples 1 to 29
Compound sub25(15g, 56mmol) and compound C (11.6g, 56mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (23.2g, 168.1mmol) was dissolved in water (70ml), added to the mixture, and the mixture was stirred well, followed by the addition of tetrakis (triphenylphosphine) palladium (0) (0.6g, 0.6 mmol). After reacting for 8 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound subC-1(16.7 g). (yield: 76%, MS: [ M + H ]]+＝394)
Compound subC-1(15g, 38.1mmol) and Compound A (10g, 38.1mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (15.8g, 114.3mmol) was dissolved in water (47ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.4 mmol). After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer was separatedAnd an aqueous layer, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 29(16 g). (yield: 73%, MS: [ M + H ]]+＝576)
Preparation examples 1 to 30
Compound sub2(15g, 47.2mmol) and compound C (9.7g, 47.2mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (19.6g, 141.6mmol) was dissolved in water (59ml), added to the mixture, and the mixture was stirred well, followed by the addition of tetrakis (triphenylphosphine) palladium (0) (0.5g, 0.5 mmol). After reacting for 8 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound subC-2(14 g). (yield: 67%, MS: [ M + H ]]+＝444)
Compound subC-2(15g, 33.8mmol) and Compound A (8.9g, 33.8mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (14g, 101.4mmol) was dissolved in water (42ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.3 mmol). After 9 hours of reaction, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. Dissolving in chloroform again, and washing with waterTwice, then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 30(13.1 g). (yield: 62%, MS: [ M + H ]]+＝626)
Preparation examples 1 to 31
Compound sub26(15g, 40.8mmol) and compound C (8.4g, 40.8mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (16.9g, 122.3mmol) was dissolved in water (51ml), added to the mixture, and the mixture was stirred well, followed by the addition of tetrakis (triphenylphosphine) palladium (0) (0.5g, 0.4 mmol). After reacting for 11 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound subC-3(13.5 g). (yield: 67%, MS: [ M + H ]]+＝494)
Compound subC-3(15g, 30.4mmol) and Compound A (8g, 30.4mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (12.6g, 91.1mmol) was dissolved in water (38ml), added to the mixture, and the mixture was stirred well, followed by the addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.3 mmol). After reacting for 10 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, then the organic layer was separated, anhydrous magnesium sulfate was added thereto, and the mixture wasStirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 31(15.6 g). (yield: 76%, MS: [ M + H ]]+＝676)
Preparation examples 1 to 32
Compound sub4(15g, 43.6mmol) and compound C (9g, 43.6mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (18.1g, 130.9mmol) was dissolved in water (54ml), added to the mixture, and the mixture was stirred well, followed by the addition of tetrakis (triphenylphosphine) palladium (0) (0.5g, 0.4 mmol). After reacting for 8 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound subC-4(16.4 g). (yield: 80%, MS: [ M + H ]]+＝470)
Compound subC-4(15g, 31.9mmol) and Compound A (8.4g, 31.9mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (13.2g, 95.8mmol) was dissolved in water (40ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.3 mmol). After reacting for 8 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. Passing the concentrated compound through siliconPurification by gel column chromatography gave compound 32(13.5 g). (yield: 65%, MS: [ M + H ]]+＝652)
Preparation examples 1 to 33
Compound sub10(15g, 38.1mmol) and compound C (7.9g, 38.1mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (15.8g, 114.3mmol) was dissolved in water (47ml), added to the mixture, and the mixture was stirred well, followed by the addition of tetrakis (triphenylphosphine) palladium (0) (0.4g, 0.4 mmol). After reacting for 12 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound subC-5(14.2 g). (yield: 72%, MS: [ M + H ]]+＝520)
Compound subC-5(15g, 28.8mmol) and Compound A (7.6g, 28.8mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (12g, 86.5mmol) was dissolved in water (36ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.1g, 0.3 mmol). After 9 hours of reaction, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 33(12.1 g). (yield: 60%, MS: [ M +)H]+＝702)
Preparation examples 1 to 34
Compound sub27(15g, 40.8mmol) and compound C (8.4g, 40.8mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (16.9g, 122.3mmol) was dissolved in water (51ml), added to the mixture, and the mixture was stirred well, followed by the addition of tetrakis (triphenylphosphine) palladium (0) (0.5g, 0.4 mmol). After reacting for 12 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound subC-6(15.7 g). (yield: 78%, MS: [ M + H ]]+＝494)
Compound subC-6(15g, 30.4mmol) and Compound A (8g, 30.4mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (12.6g, 91.1mmol) was dissolved in water (38ml), added to the mixture, and the mixture was stirred well, followed by the addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.3 mmol). After reacting for 10 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 34(15.2 g). (yield: 74%, MS: [ M + H ]]+＝676)
Preparation examples 1 to 35
Compound sub34(15g, 39.1mmol) and compound C (8.1g, 39.1mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (16.2g, 117.2mmol) was dissolved in water (49ml), added to the mixture, and the mixture was stirred well, followed by the addition of tetrakis (triphenylphosphine) palladium (0) (0.5g, 0.4 mmol). After 9 hours of reaction, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound subC-7(15.9 g). (yield: 80%, MS: [ M + H ]]+＝510)
Compound subC-7(15g, 29.4mmol) and Compound A (7.7g, 29.4mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (12.2g, 88.2mmol) was dissolved in water (37ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.3 mmol). After 9 hours of reaction, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 35(14.2 g). (yield: 70%, MS: [ M + H ]]+＝692)
Preparation examples 1 to 36
Compound sub28(15g, 34.6mmol) and compound C (7.2g, 34.6mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (14.4g, 103.9mmol) was dissolved in water (43ml), added to the mixture, and the mixture was stirred well, followed by the addition of tetrakis (triphenylphosphine) palladium (0) (0.4g, 0.3 mmol). After reacting for 8 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound subC-8(13.3 g). (yield: 69%, MS: [ M + H ]]+＝559)
Compound subC-8(15g, 26.8mmol) and Compound A (7g, 26.8mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (11.1g, 80.5mmol) was dissolved in water (33ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.1g, 0.3 mmol). After reacting for 12 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 36(15.5 g). (yield: 78%, MS: [ M + H ]]+＝741)
Preparation examples 1 to 37
Compound sub19(15g, 34.6mmol) and compound C (7.2g, 34.6mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (14.4g, 103.9mmol) was dissolved in water (43ml), added to the mixture, and the mixture was stirred well, followed by the addition of tetrakis (triphenylphosphine) palladium (0) (0.4g, 0.3 mmol). After reacting for 10 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound subC-9(13.9 g). (yield: 72%, MS: [ M + H ]]+＝559)
Compound subC-9(15g, 26.8mmol) and Compound A (7g, 26.8mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (11.1g, 80.5mmol) was dissolved in water (33ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.1g, 0.3 mmol). After reacting for 11 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 37(14.5 g). (yield: 73%, MS: [ M + H ]]+＝741)
Preparation examples 1 to 38
Under nitrogenCompound sub12(15g, 41.9mmol) and compound C (8.7g, 41.9mmol) were added to THF (300ml) under atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (17.4g, 125.8mmol) was dissolved in water (52ml), added to the mixture, and the mixture was stirred well, followed by the addition of tetrakis (triphenylphosphine) palladium (0) (0.5g, 0.4 mmol). After 9 hours of reaction, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound subC-10(14.2 g). (yield: 70%, MS: [ M + H ]]+＝484)
Compound subC-10(15g, 31mmol) and Compound A (8.1g, 31mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (12.9g, 93mmol) was dissolved in water (39ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.3 mmol). After reacting for 10 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 38(13.4 g). (yield: 65%, MS: [ M + H ]]+＝666)
Preparation examples 1 to 39
Compound sub14(15g, 36.8mmol) and Compound C (7.6g, 36.8mmol) were added under a nitrogen atmosphere toTHF (300ml) and the mixture was stirred and refluxed. Then, potassium carbonate (15.2g, 110.3mmol) was dissolved in water (46ml), added to the mixture, and the mixture was stirred well, followed by the addition of tetrakis (triphenylphosphine) palladium (0) (0.4g, 0.4 mmol). After reacting for 12 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound subC-11(12.9 g). (yield: 66%, MS: [ M + H ]]+＝534)
Compound subC-11(15g, 28.1mmol) and Compound A (7.4g, 28.1mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (11.6g, 84.3mmol) was dissolved in water (35ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.1g, 0.3 mmol). After 9 hours of reaction, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 39(14.5 g). (yield: 72%, MS: [ M + H ]]+＝716)
Preparation examples 1 to 40
Compound sub29(15g, 36.8mmol) and compound C (7.6g, 36.8mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (15)2g, 110.3mmol) was dissolved in water (46ml), added to the mixture and the mixture was stirred well before tetrakis (triphenylphosphine) palladium (0) (0.4g, 0.4mmol) was added. After reacting for 12 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound subC-12(12.9 g). (yield: 66%, MS: [ M + H ]]+＝534)
Compound subC-12(15g, 28.1mmol) and Compound A (7.4g, 28.1mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (11.6g, 84.3mmol) was dissolved in water (35ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.1g, 0.3 mmol). After 9 hours of reaction, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 40(12.7 g). (yield: 63%, MS: [ M + H ]]+＝716)
Preparation examples 1 to 41
Compound sub30(15g, 35.5mmol) and compound C (7.3g, 35.5mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (14.7g, 106.4mmol) was dissolved in water (44ml), added to the mixture, and the mixture was mixedThe mixture was stirred well and then tetrakis (triphenylphosphine) palladium (0) (0.4g, 0.4mmol) was added. After reacting for 12 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound subC-13(14.6 g). (yield: 75%, MS: [ M + H ]]+＝550)
Compound subC-13(15g, 27.3mmol) and Compound A (7.1g, 27.3mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (11.3g, 81.8mmol) was dissolved in water (34ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.1g, 0.3 mmol). After reacting for 8 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 41(13.6 g). (yield: 68%, MS: [ M + H ]]+＝732)
Preparation examples 1 to 42
Compound sub17(15g, 40.1mmol) and compound C (8.3g, 40.1mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (16.6g, 120.4mmol) was dissolved in water (50ml), added to the mixture, and the mixture was stirred well, followed by the addition of tetrakis (triphenylphosphine) palladium (0) (0.5g, 0.4 mmol).After reacting for 8 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give the compound subC-14(13 g). (yield: 65%, MS: [ M + H ]]+＝500)
Compound subC-14(15g, 30mmol) and Compound A (7.9g, 30mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (12.4g, 90mmol) was dissolved in water (37ml), added to the mixture, and the mixture was sufficiently stirred, followed by addition of bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.3 mmol). After reacting for 8 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 42(14.7 g). (yield: 72%, MS: [ M + H ]]+＝682)
Preparation example 2-1
Compound A (15g, 58.3mmol) and compound B (10g, 64.2mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (24.2g, 175mmol) was dissolved in water (73ml), added to the mixture, and the mixture was stirred well, followed by the addition of tetrakis (triphenylphosphine) palladium (0) (0.7g, 0.6 mmol). After reacting for 11 hours, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated,the organic layer was then distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound ba-1(10.4 g). (yield: 62%, MS: [ M + H ]]+＝289)
Compound sub a-1(10g, 34.6mmol), compound sub1(11.1g, 34.6mmol) and sodium tert-butoxide (6.7g, 69.3mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was added thereto. After 3 hours of reaction, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 2-1(13.3 g). (yield: 67%, MS: [ M + H ]]+＝574)
Preparation examples 2 to 2
Compound sub a-1(10g, 34.6mmol), compound sub2(12.9g, 34.6mmol) and sodium tert-butoxide (6.7g, 69.3mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was added thereto. When the reaction was complete after 2 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. Subjecting the concentrated compound to silica gel column chromatographyPurification was carried out to give compound 2-2(11 g). (yield: 51%, MS: [ M + H ]]+＝624)
Preparation examples 2 to 3
Compound sub a-1(10g, 34.6mmol), compound sub3(14.6g, 34.6mmol) and sodium tert-butoxide (6.7g, 69.3mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was added thereto. When the reaction was complete after 3 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 2-3(14 g). (yield: 60%, MS: [ M + H ]]+＝674)
Preparation examples 2 to 4
Compound sub a-1(10g, 34.6mmol), compound sub4(13.8g, 34.6mmol) and sodium tert-butoxide (6.7g, 69.3mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was added thereto. When the reaction was complete after 3 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 2-4(12.4 g). (yield: 55%, MS: [ M + H ]]+＝650)
Preparation examples 2 to 5
Compound sub a-1(10g, 34.6mmol), compound sub5(12.9g, 34.6mmol) and sodium tert-butoxide (6.7g, 69.3mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was added thereto. When the reaction was complete after 3 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 2-5(12.7 g). (yield: 59%, MS: [ M + H ]]+＝624)
Preparation examples 2 to 6
Compound sub a-1(10g, 34.6mmol), compound sub6(14.3g, 34.6mmol) and sodium tert-butoxide (6.7g, 69.3mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was added thereto. When the reaction was complete after 3 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compounds 2-6(15.4 g). (yield: 67%, MS: [ M + H ]]+＝664)
Preparation examples 2 to 7
In nitrogenCompound sub a-1(10g, 34.6mmol), compound sub7(17.4g, 34.6mmol) and sodium tert-butoxide (6.7g, 69.3mmol) were added to xylene (200ml) under a gas atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was added thereto. When the reaction was complete after 3 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compounds 2-7(17.3 g). (yield: 66%, MS: [ M + H ]]+＝756)
Preparation examples 2 to 8
Compound sub a-1(10g, 34.6mmol), compound sub8(11.6g, 34.6mmol) and sodium tert-butoxide (6.7g, 69.3mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was added thereto. When the reaction was complete after 2 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compounds 2-8(13.8 g). (yield: 68%, MS: [ M + H ]]+＝588)
Preparation examples 2 to 9
Compound sub a-1(10g, 34.6mmol), compound sub9(11.6g, 34.6mmol) and sodium tert-butoxide (6.7g, 69.3mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, the user can use the device to perform the operation,to this was added bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3 mmol). When the reaction was complete after 2 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compounds 2-9(10.6 g). (yield: 52%, MS: [ M + H ]]+＝588)
Preparation examples 2 to 10
Compound sub a-1(10g, 34.6mmol), compound sub10(12.5g, 34.6mmol) and sodium tert-butoxide (6.7g, 69.3mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was added thereto. When the reaction was complete after 3 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compounds 2-10(11.5 g). (yield: 54%, MS: [ M + H ]]+＝614)
Preparation examples 2 to 11
Compound sub a-1(10g, 34.6mmol), compound sub11(15.2g, 34.6mmol) and sodium tert-butoxide (6.7g, 69.3mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was added thereto. When the reaction was complete after 2 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, will combineThe substance was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compounds 2-11(13.6 g). (yield: 57%, MS: [ M + H ]]+＝690)
Preparation examples 2 to 12
Compound sub a-1(10g, 34.6mmol), compound sub12(13.9g, 34.6mmol) and sodium tert-butoxide (6.7g, 69.3mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was added thereto. When the reaction was complete after 3 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compounds 2-12(15.8 g). (yield: 70%, MS: [ M + H ]]+＝654)
Preparation examples 2 to 13
Compound sub a-1(10g, 34.6mmol), compound sub13(115.5g, 34.6mmol) and sodium tert-butoxide (6.7g, 69.3mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was added thereto. When the reaction was complete after 2 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. Concentrating the obtained compoundPurification by silica gel column chromatography gave compounds 2-13(13.8 g). (yield: 68%, MS: [ M + H ]]+＝588)
Preparation examples 2 to 14
Compound sub a-1(10g, 34.6mmol), compound sub14(13.8g, 34.6mmol) and sodium tert-butoxide (6.7g, 69.3mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was added thereto. When the reaction was complete after 2 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compounds 2-14(14.8 g). (yield: 66%, MS: [ M + H ]]+＝650)
Preparation examples 2 to 15
Compound sub a-1(10g, 34.6mmol), compound sub15(13.8g, 34.6mmol) and sodium tert-butoxide (6.7g, 69.3mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was added thereto. When the reaction was complete after 2 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compounds 2-15(14.4 g). (yield: 64%, MS: [ M + H ]]+＝650)
Preparation examples 2 to 16
Compound sub a-1(10g, 34.6mmol), compound sub16(16.4g, 34.6mmol) and sodium tert-butoxide (6.7g, 69.3mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was added thereto. When the reaction was complete after 3 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compounds 2-16(13.1 g). (yield: 52%, MS: [ M + H ]]+＝726)
Preparation examples 2 to 17
Compound sub a-1(10g, 34.6mmol), compound sub17(16.4g, 34.6mmol) and sodium tert-butoxide (6.7g, 69.3mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was added thereto. When the reaction was complete after 2 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compounds 2-17(16.6 g). (yield: 66%, MS: [ M + H ]]+＝726)
Preparation examples 2 to 18
Compound sub a-1(10g, 34.6mmol), compound sub18(11.1g, 34.6mmol) and sodium tert-butoxide (6.7g, 69.3mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was added thereto. When the reaction was complete after 2 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compounds 2-18(11.1 g). (yield: 56%, MS: [ M + H ]]+＝572)
Preparation examples 2 to 19
Compound sub a-1(10g, 34.6mmol), compound sub19(15g, 34.6mmol) and sodium tert-butoxide (6.7g, 69.3mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was added thereto. When the reaction was complete after 2 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compounds 2-19(16.4 g). (yield: 69%, MS: [ M + H ]]+＝687)
Preparation examples 2 to 20
Compound subA-1(10g, 34.6mmol), compound sub20(13.7g, 34.6mmol) and sodium tert-butoxide (6.7g, 69.3mmol) were added to xylene (200ml) under a nitrogen atmosphere, andthe mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was added thereto. When the reaction was complete after 3 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compounds 2-20(15 g). (yield: 67%, MS: [ M + H ]]+＝648)
Preparation examples 2 to 21
Compound sub a-1(10g, 34.6mmol), compound sub21(11.1g, 34.6mmol) and sodium tert-butoxide (6.7g, 69.3mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was added thereto. When the reaction was complete after 3 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compounds 2-21(10.5 g). (yield: 53%, MS: [ M + H ]]+＝572)
Preparation examples 2 to 22
Compound a (15g, 58.3mmol) and compound C (10g, 64.2mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (24.2g, 175mmol) was dissolved in water (73ml), added to the mixture, and the mixture was stirred well, followed by the addition of tetrakis (triphenylphosphine) palladium (0) (0.7g, 0.6 mmol). After 8 hours of reaction, the reaction mixture isThe mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound ba-2(12.4 g). (yield: 74%, MS: [ M + H ]]+＝289)
Compound sub a-2(10g, 34.6mmol), compound sub22(12g, 34.6mmol) and sodium tert-butoxide (6.7g, 69.3mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was added thereto. When the reaction was complete after 2 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compounds 2-22(14.1 g). (yield: 68%, MS: [ M + H ]]+＝598)
Preparation examples 2 to 23
Compound sub a-1(10g, 34.6mmol), compound sub23(12g, 34.6mmol) and sodium tert-butoxide (6.7g, 69.3mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was added thereto. When the reaction was complete after 2 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, andthe filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compounds 2-23(11 g). (yield: 53%, MS: [ M + H ]]+＝598)
Preparation examples 2 to 24
Compound sub a-2(10g, 34.6mmol), compound sub24(17.7g, 34.6mmol) and sodium tert-butoxide (6.7g, 69.3mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was added thereto. When the reaction was complete after 3 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compounds 2-24(15.3 g). (yield: 58%, MS: [ M + H ]]+＝763)
Preparation examples 2 to 25
Compound sub25(10g, 59.1mmol), compound sub A-1(34.1g, 118.2mmol) and sodium tert-butoxide (17g, 177.3mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.6g, 1.2mmol) was added thereto. When the reaction was complete after 3 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compounds 2-25(27.1 g). (yield: 68%, MS: [ M + H ]]+＝674)
Preparation examples 2 to 26
Compound sub26(10g, 51.7mmol), compound sub A-1(29.9g, 103.5mmol) and sodium tert-butoxide (14.9g, 155.2mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.5g, 1mmol) was added thereto. When the reaction was complete after 3 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compounds 2-26(18 g). (yield: 50%, MS: [ M + H ]]+＝698)
Preparation examples 2 to 27
Compound sub27(10g, 30mmol), compound sub A-1(17.3g, 60mmol) and sodium tert-butoxide (8.6g, 90mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.6mmol) was added thereto. When the reaction was complete after 2 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compounds 2-27(14.6 g). (yield: 58%, MS: [ M + H ]]+＝838)
Preparation examples 2 to 28
Compound sub a-2(10g, 34.6mmol), compound sub28(7.2g, 34.6mmol) and sodium tert-butoxide (6.7g, 69.3mmol) were added to toluene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was added thereto. When the reaction was complete after 3 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound subA-2-1(11.2 g). (yield: 70%, MS: [ M + H ]]+＝462)
Compound subA-2-1(10g, 21.7mmol), compound subA-1(6.3g, 21.7mmol) and sodium t-butoxide (4.2g, 43.3mmol) were added to xylene (200ml) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.1g, 0.2mmol) was added thereto. When the reaction was complete after 3 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compounds 2-28(10.7 g). (yield: 69%, MS: [ M + H ]]+＝714)
Preparation examples 2 to 29
Compound subA-2(10g, 34.6mmol), compound sub29(8.5g, 34.6mmol) and sodium tert-butoxide (6.7g, 69.3mmol) were added to toluene (200ml) under a nitrogen atmosphere, andthe mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was added thereto. When the reaction was complete after 2 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound ba-2-2(9.8 g). (yield: 57%, MS: [ M + H ]]+＝498)
Compound subA-2-2(10g, 20.1mmol), compound subA-1(5.8g, 20.1mmol) and sodium tert-butoxide (3.9g, 40.2mmol) were added to xylene (200ml) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.1g, 0.2mmol) was added thereto. When the reaction was complete after 2 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compounds 2-29(10.1 g). (yield: 67%, MS: [ M + H ]]+＝750)
Preparation examples 2 to 30
Compound D (15g, 45mmol) and compound B (7.7g, 49.5mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (18.7g, 135mmol) was dissolved in water (56ml), added to the mixture, and the mixture was stirred well, followed by the addition of tetrakis (triphenylphosphine) palladium (0) (0.5g, 0.5 mmol). After 10 hours of reaction, the reaction mixture was cooled to room temperature and the organic phase was separatedLayers and aqueous layer, then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound subD-1(13.1 g). (yield: 80%, MS: [ M + H ]]+＝365)
Compound subD-1(10g, 27.4mmol), compound sub22(9.5g, 27.4mmol) and sodium tert-butoxide (5.3g, 54.8mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.1g, 0.3mmol) was added thereto. When the reaction was complete after 2 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compounds 2-30(9.6 g). (yield: 52%, MS: [ M + H ]]+＝674)
Preparation examples 2 to 31
Compound subD-1(10g, 27.4mmol), compound sub30(11.5g, 27.4mmol) and sodium tert-butoxide (5.3g, 54.8mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.1g, 0.3mmol) was added thereto. When the reaction was complete after 2 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. ConcentratingThe compound was purified by silica gel column chromatography to give compounds 2-31(13.9 g). (yield: 68%, MS: [ M + H ]]+＝748)
Preparation examples 2 to 32
Compound D (15g, 45mmol) and compound C (7.7g, 49.5mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (18.7g, 135mmol) was dissolved in water (56ml), added to the mixture, and the mixture was stirred well, followed by the addition of tetrakis (triphenylphosphine) palladium (0) (0.5g, 0.5 mmol). After 9 hours of reaction, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound subD-2(9.3 g). (yield: 72%, MS: [ M + H ]]+＝289)
Compound subD-2(10g, 27.4mmol), compound sub31(12.4g, 27.4mmol) and sodium tert-butoxide (5.3g, 54.8mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.1g, 0.3mmol) was added thereto. When the reaction was complete after 2 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compounds 2-32(15 g). (yield: 70%, MS: [ M + H ]]+＝780)
Preparation examples 2 to 33
Compound A (15g, 58.3mmol) and compound E (14.9g, 64.2mmol) were added to THF (300ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (24.2g, 175mmol) was dissolved in water (73ml), added to the mixture, and the mixture was stirred well, followed by the addition of tetrakis (triphenylphosphine) palladium (0) (0.7g, 0.6 mmol). After reacting for 10 hours, the reaction mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and then the organic layer was distilled. It was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound ba-3(14.9 g). (yield: 70%, MS: [ M + H ]]+＝365)
Compound sub a-3(10g, 27.4mmol), compound sub32(2.6g, 27.4mmol) and sodium tert-butoxide (5.3g, 54.8mmol) were added to toluene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.1g, 0.3mmol) was added thereto. When the reaction was complete after 2 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound subA-3-1(5.8 g). (yield: 50%, MS: [ M + H ]]+＝422)
Compound subA-3-1(10g, 23.7mmol), compound subA-2(6.9g, 23.7mmol) and sodium tert-butoxide (4.6g, 47.4mmol) were added to toluene (200ml) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.1g, 0.2mmol) was added thereto. When the reaction was complete after 2 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compounds 2-33(8.9 g). (yield: 56%, MS: [ M + H ]]+＝674)
Preparation examples 2 to 34
Compound sub a-3(10g, 27.4mmol), compound sub33(4.6g, 27.4mmol) and sodium tert-butoxide (5.3g, 54.8mmol) were added to toluene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.1g, 0.3mmol) was added thereto. When the reaction was complete after 3 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound subA-3-2(9.1 g). (yield: 67%, MS: [ M + H ]]+＝498)
Compound subA-3-2(10g, 20.1mmol), compound subA-2(5.8g, 20.1mmol) and sodium tert-butoxide (3.9g, 40.2mmol) were added to xylene (200ml) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, adding into itBis (tri-tert-butylphosphino) palladium (0) (0.1g, 0.2mmol) was added. When the reaction was complete after 2 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compounds 2-34(9.6 g). (yield: 64%, MS: [ M + H ]]+＝750)
Preparation examples 2 to 35
Compound subA-3-2(10g, 20.1mmol), compound subA-1(5.8g, 20.1mmol) and sodium tert-butoxide (3.9g, 40.2mmol) were added to xylene (200ml) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.1g, 0.2mmol) was added thereto. When the reaction was complete after 3 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compounds 2-35(8.6 g). (yield: 57%, MS: [ M + H ]]+＝750)
Preparation examples 2 to 36
Compound sub a-3(10g, 27.4mmol), compound sub34(4.6g, 27.4mmol) and sodium tert-butoxide (5.3g, 54.8mmol) were added to toluene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.1g, 0.3mmol) was added thereto. When the reaction was complete after 3 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound is again completedDissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound subA-3-3(8.6 g). (yield: 63%, MS: [ M + H ]]+＝498)
Compound subA-3-3(10g, 20.1mmol), compound subA-2(5.8g, 20.1mmol) and sodium tert-butoxide (3.9g, 40.2mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.1g, 0.2mmol) was added thereto. When the reaction was complete after 2 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compounds 2-36(10.4 g). (yield: 69%, MS: [ M + H ]]+＝750)
Preparation examples 2 to 37
Compound sub35(10g, 51.7mmol), compound sub A-2(29.9g, 103.5mmol) and sodium tert-butoxide (14.9g, 155.2mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.5g, 1mmol) was added thereto. When the reaction was complete after 2 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 2-37(23.8g). (yield: 66%, MS: [ M + H ]]+＝698)
Preparation examples 2 to 38
Compound sub33(10g, 107.4mmol), compound sub D-1(78.4g, 214.8mmol) and sodium tert-butoxide (31g, 322.1mmol) were added to xylene (200ml) under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (1.1g, 2.1mmol) was added thereto. When the reaction was complete after 2 hours, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 2-38(53.9 g). (yield: 67%, MS: [ M + H ]]+＝750)
[ examples ]
Example 1
Is coated with
The glass substrate of ITO (indium tin oxide) thin film of thickness of (a) was put in distilled water containing a detergent dissolved therein and washed by ultrasonic waves. In this case, the detergent used was a commercially available product from Fisher co, and the distilled water was distilled water filtered twice by using a commercially available filter from Millipore co. The ITO was washed for 30 minutes, and then the ultrasonic washing was repeated twice for 10 minutes by using distilled water. After completion of the washing with distilled water, the substrate was ultrasonically washed with isopropyl alcohol, acetone and methanol solvents, and dried, before being transferred to a plasma cleaner. The substrate was then rinsed with oxygen plasma for 5 minutes and then transferred to a vacuum evaporator.
Forming an ITO transparent electrode prepared thereby to have a thickness of
The following compound HI-1 was used as a hole injection layer, but the following compound a-1 was p-doped at a concentration of 1.5 wt%. Vacuum depositing the following compound HT-1 on the hole injection layer to form a film thickness of
The hole transport layer of (1). Then, the following compound EB-1 was vacuum-deposited on the hole transport layer to form a film thickness of
The electron blocking layer of (1). Then, the previously prepared compound 1 and compound 2-1 as hosts, and the following compound Dp-7 as a dopant were vacuum-deposited on the electron blocking layer at a weight ratio of 49:49:2, respectively, to form a film thickness of
The light emitting layer of (1). Vacuum depositing the following compound HB-1 on the light-emitting layer to form a film thickness of
A hole blocking layer of (2). The following compound ET-1 and the following compound LiQ were vacuum deposited on the hole-blocking layer at a ratio of 2:1 to form a film thickness of
Electron injection and transport layers. Sequentially depositing lithium fluoride (LiF) and aluminum on the electron injecting and transporting layer to a thickness of
And
thereby forming a cathode.
In the above process, the deposition rate of the organic material is maintained at
Second to
Second, the deposition rates of lithium fluoride and aluminum of the cathode are respectively maintained at
Second and
second, and the degree of vacuum during deposition was maintained at 2X 10-7Hold in the palm to 5 x 10-6And supporting to thereby manufacture an organic light emitting device.
Examples 2 to 100
An organic light emitting device was manufactured in the same manner as in example 1, except that the compounds shown in tables 1 to 3 below were used as hosts of the light emitting layer.
Comparative examples 1 to 85
An organic light-emitting device was fabricated in the same manner as in example 1, except that the compounds shown in tables 4 to 7 below were used as hosts of the light-emitting layer. In the following tables 6 and 7, it means that a single compound is used as a host of the light emitting layer, and the compounds in table 7 are respectively as follows.
By applying a current (15 mA/cm) to the organic light emitting devices manufactured in examples and comparative examples2) The driving voltage, the light emitting efficiency, and the lifetime were measured, and the results are shown in tables 1 to 7 below. The lifetime T95 means the time (hours) required for the luminance to decrease to 95% of the initial luminance (6000 nit).
[ Table 1]
[ Table 2]
[ Table 3]
[ Table 4]
[ Table 5]
[ Table 6]
| Classification | Main body | Efficiency (cd/A) | Life T95 (hours) | Color of light emission |
| Comparative example 49 | |
20.3 | 122 | Red colour |
| Comparative example 50 | |
21.1 | 135 | Red colour |
| Comparative example 51 | Compound (I)5 | 23.2 | 148 | Red colour |
| Comparative example 52 | Compound 9 | 22.6 | 127 | Red colour |
| Comparative example 53 | Compound 10 | 21.8 | 143 | Red colour |
| Comparative example 54 | Compound 14 | 23.2 | 157 | Red colour |
| Comparative example 55 | Compound 17 | 22.6 | 145 | Red colour |
| Comparative example 56 | Compound 19 | 21.4 | 128 | Red colour |
| Comparative example 57 | Compound 21 | 24.5 | 172 | Red colour |
| Comparative example 58 | Compound 23 | 19.4 | 126 | Red colour |
| Comparative example 59 | Compound 25 | 20.2 | 129 | Red colour |
| Comparative example 60 | Compound 29 | 21.3 | 141 | Red colour |
| Comparative example 61 | Compound 30 | 21.5 | 133 | Red colour |
| Comparative example 62 | Compound 31 | 20.2 | 145 | Red colour |
| Comparative example 63 | Compound 32 | 21.6 | 157 | Red colour |
| Comparative example 64 | Compound 33 | 22.3 | 140 | Red colour |
| Comparative example 65 | Compound 34 | 21.6 | 152 | Color of fiber |
| Comparative example 66 | Compound 35 | 22.2 | 143 | Red colour |
| Comparative example 67 | Compound 36 | 22.8 | 142 | Red colour |
| Comparative example 68 | Compound 37 | 21.6 | 158 | Red colour |
| Comparative example 69 | Compound 38 | 22.3 | 141 | Red colour |
| Comparative example 70 | Compound 39 | 21.5 | 151 | Red colour |
| Comparative example 71 | Compound 40 | 20.7 | 160 | Red colour |
| Comparative example 72 | Compound 41 | 22.6 | 159 | Color of fiber |
| Comparative example 73 | Compound 42 | 23.8 | 163 | Red colour |
[ Table 7]
| Classification | Main body | Efficiency (cd/A) | Life T95 (hours) | Color of light emission |
| Comparative example 74 | C-1 | 17.4 | 107 | Red colour |
| Comparative example 75 | C-2 | 16.1 | 83 | Red colour |
| Comparative example 76 | C-3 | 16.4 | 94 | Red colour |
| Comparative example 77 | C-4 | 16.0 | 87 | Red colour |
| Comparative example 78 | C-5 | 18.7 | 110 | Red colour |
| Comparative example 79 | C-6 | 16.5 | 47 | Red colour |
| Comparative example 80 | C-7 | 15.3 | 22 | Red colour |
| Comparative example 81 | C-8 | 15.1 | 37 | Red colour |
| Comparative example 82 | C-9 | 17.3 | 75 | Red colour |
| Comparative example 83 | C-10 | 17.5 | 92 | Red colour |
| Comparative example 84 | C-11 | 15.8 | 63 | Red colour |
| ComparisonExample 85 | C-12 | 16.1 | 78 | Red colour |
As shown in the above table, the organic light emitting device of the embodiment in which the first compound represented by chemical formula 1 and the second compound represented by chemical formula 2 are simultaneously used as the host material of the light emitting layer exhibited excellent light emitting efficiency and significantly improved life characteristics, compared to the organic light emitting device of the comparative example in which only one of the compound represented by chemical formula 1 and the compound represented by chemical formula 2 (table 6) or neither of them is used (table 7). In particular, the device according to the embodiment shows higher efficiency and longer life span than the device of the comparative example in which the compound represented by chemical formula 1 is used as a single host. In addition, the devices according to the embodiments show improved efficiency and lifetime characteristics even compared to the devices of the comparative examples in which the compounds C-1 to C-12 of the comparative examples are used as the first host and the compound represented by chemical formula 2 is used as the second host. From this, it was confirmed that when a combination of the first compound represented by chemical formula 1 and the second compound represented by chemical formula 2 is used as a co-host, energy transfer to the red dopant is efficiently performed in the red light emitting layer. This can be judged because the first compound has high electron and hole stability, and further, because the amount of holes increases with the simultaneous use of the second compound, and therefore the electrons and holes in the red light-emitting layer maintain a more stable balance.
Therefore, when the first compound and the second compound are simultaneously used as host materials of the organic light emitting device, it is determined that the driving voltage, the light emitting efficiency, and/or the lifetime characteristics of the organic light emitting device can be improved. In general, it may be considered that the organic light emitting device employing the combination of the compounds of the present disclosure exhibits significantly improved device characteristics compared to the device of the comparative example, considering that the light emitting efficiency and the lifetime characteristics of the organic light emitting device have a trade-off relationship with each other.
Description of the reference numerals
1: substrate 2: anode
3: light-emitting layer 4: cathode electrode
5: hole transport layer 6: electron transport layer
Claims (12)
1. An organic light emitting device comprising:
an anode, a cathode, a anode and a cathode,
a cathode, and
a light emitting layer interposed between the anode and the cathode,
wherein the light emitting layer includes a compound represented by the following chemical formula 1 and a compound represented by the following chemical formula 2:
[ chemical formula 1]
In the chemical formula 1, the first and second,
x is O or S, and X is O or S,
each Y is independently N or CH, provided that at least one Y is N,
L1is a single bond, or substituted or unsubstituted C6-60An arylene group, a cyclic or cyclic alkylene group,
Ar1and Ar2Each independently is substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O and S2-60(ii) a heteroaryl group, wherein,
[ chemical formula 2]
In the chemical formula 2, the first and second organic solvents,
L2is substituted or unsubstituted C6-60An arylene group, a cyclic or cyclic alkylene group,
L3and L4Each independently is a single bondOr substituted or unsubstituted C6-60An arylene group, a cyclic or cyclic alkylene group,
Ar3and Ar4Each independently is substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O and S2-60(ii) a heteroaryl group, wherein,
r is hydrogen, deuterium, or substituted or unsubstituted C6-60Aryl, and
n is an integer of 0 to 9.
2. The organic light emitting device according to claim 1,
wherein all Y are N.
3. The organic light emitting device according to claim 1,
wherein L is1Is a single bond, phenylene or naphthylene.
4. The organic light emitting device according to claim 1,
wherein L is1Is a single bond,
5. The organic light emitting device according to claim 1,
wherein Ar is1And Ar2Each independently is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, (phenyl) naphthyl, (naphthyl) phenyl, dimethylfluorenyl, diphenylfluorenyl, dibenzofuranyl, dibenzothienyl, carbazol-9-yl, 9-phenyl-9H-carbazolyl, and
ar is1And Ar2Each independently unsubstituted or substituted with at least one deuterium.
6. The organic light emitting device according to claim 1,
wherein Ar is1Is phenyl, biphenyl or naphthyl,
ar is1Unsubstituted or substituted by at least one deuterium, and
Ar2is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, (phenyl) naphthyl, (naphthyl) phenyl, dimethylfluorenyl, diphenylfluorenyl, dibenzofuranyl, dibenzothienyl, carbazol-9-yl, 9-phenyl-9H-carbazolyl,
ar is2Unsubstituted or substituted with at least one deuterium.
7. The organic light emitting device according to claim 1,
wherein the compound represented by chemical formula 1 is any one selected from the group consisting of:
8. the organic light emitting device according to claim 1,
wherein chemical formula 2 is represented by the following chemical formula 2-1:
[ chemical formula 2-1]
In the chemical formula 2-1, the,
R1is hydrogen, deuterium or phenyl,
n1 is an integer from 0 to 8,
L2、L3、L4、Ar3、Ar4and R is as defined in claim 1.
9. The organic light emitting device according to claim 1,
wherein L is2Is phenylene or phenylene substituted with at least one deuterium.
10. The organic light emitting device according to claim 1,
wherein L is3And L4Each independently a single bond, phenylene, biphenyldiyl, or naphthylene,
said L3And L4Each independently unsubstituted or substituted with at least one deuterium.
11. The organic light emitting device according to claim 1,
wherein Ar is3And Ar4Each independently is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, (phenyl) phenanthryl, triphenylene, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, diphenylfluorenyl, dibenzofuranyl, (phenyl) dibenzofuranyl, phenylthiofuranyl, and optionally,Dibenzothienyl, (phenyl) dibenzothienyl, carbazol-9-yl or 9-phenyl-9H-carbazolyl,
ar is3And Ar4Each independently unsubstituted or substituted with at least one deuterium.
12. The organic light emitting device according to claim 1,
wherein the compound represented by chemical formula 2 is any one selected from the group consisting of:
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| CN114773325A (en) * | 2022-03-31 | 2022-07-22 | 北京云基科技有限公司 | Compound containing triazine structure and application thereof |
| CN116217409A (en) * | 2022-03-24 | 2023-06-06 | 江苏三月科技股份有限公司 | Aromatic amine compound and organic electroluminescent device prepared from same |
| WO2023201590A1 (en) * | 2022-04-20 | 2023-10-26 | 京东方科技集团股份有限公司 | Light-emitting material for organic light-emitting device, light-emitting device, and display device |
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| KR20230021626A (en) * | 2021-08-05 | 2023-02-14 | 주식회사 엘지화학 | Organic light emitting device |
| KR20230057737A (en) | 2021-10-22 | 2023-05-02 | 롬엔드하스전자재료코리아유한회사 | A plurality of host materials and organic electroluminescent device comprising the same |
| KR20230059218A (en) | 2021-10-26 | 2023-05-03 | 롬엔드하스전자재료코리아유한회사 | A plurality of host materials and organic electroluminescent device comprising the same |
| WO2024014866A1 (en) * | 2022-07-13 | 2024-01-18 | 솔루스첨단소재 주식회사 | Organic compound and organic electroluminescent device using same |
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