CN116323621A - Novel compound and organic light emitting device comprising the same - Google Patents
Novel compound and organic light emitting device comprising the same Download PDFInfo
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- CN116323621A CN116323621A CN202180065246.5A CN202180065246A CN116323621A CN 116323621 A CN116323621 A CN 116323621A CN 202180065246 A CN202180065246 A CN 202180065246A CN 116323621 A CN116323621 A CN 116323621A
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
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- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 1
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- 229910052796 boron Inorganic materials 0.000 description 1
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- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
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- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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- NHVNWPIMHDTDPP-UHFFFAOYSA-N dibenzothiophen-3-ylboronic acid Chemical compound C1=CC=C2C3=CC=C(B(O)O)C=C3SC2=C1 NHVNWPIMHDTDPP-UHFFFAOYSA-N 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
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- 238000007641 inkjet printing Methods 0.000 description 1
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- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
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- 239000011777 magnesium Substances 0.000 description 1
- AMTZBMRZYODPHS-UHFFFAOYSA-N manganese;quinolin-8-ol Chemical compound [Mn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 AMTZBMRZYODPHS-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
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- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
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- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000010345 tape casting Methods 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
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-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
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 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
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 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
- 238000004506 ultrasonic cleaning Methods 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present disclosure relates to novel compounds and organic light emitting devices comprising the same.
Description
Technical Field
The present disclosure relates to novel compounds and organic light emitting devices comprising the same.
Background
In general, an organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy by using an organic material. An organic light emitting device using the organic light emitting phenomenon has characteristics such as a wide viewing angle, excellent contrast, a fast response time, excellent brightness, driving voltage, and response speed, and thus many researches have been conducted.
The 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 often has a multi-layered structure including different materials to improve efficiency and stability of the organic light emitting device, 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, 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.
There is a continuing need to develop new materials for organic materials used in organic light emitting devices as described above.
Prior art literature
Patent literature
(patent document 1) Korean unexamined patent publication No. 10-2000-0051826
Disclosure of Invention
Technical problem
The present disclosure relates to novel organic light emitting materials and organic light emitting devices comprising the same.
Technical proposal
In the present disclosure, there is provided a compound represented by the following chemical formula 1:
[ chemical formula 1]
In the chemical formula 1, the chemical formula is shown in the drawing,
a is a thiazole ring or condensed with an adjacent ring
An azole ring, wherein the azole ring,
L 1 is a single bond; substituted or unsubstituted C 6-60 Arylene groups; or substituted or unsubstituted C comprising at least one selected from N, O and S 2-60 A heteroarylene group,
R 1 is that
Ar 1 To Ar 4 Each independently is a substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising at least one selected from N, O and S 2-60 A heteroaryl group, which is a group,
L 2 to L 5 Each independently is a single bond; substituted or unsubstituted C 6-60 Arylene groups; or substituted or unsubstituted C comprising at least one selected from N, O and S 2-60 A heteroarylene group,
R 2 is C substituted or unsubstituted 6-60 An aryl group; or substituted or unsubstituted C comprising at least one selected from N, O and S 2-60 A heteroaryl group, which is a group,
d is deuterium
n is an integer of 0 or more and 5 or less.
Further, there is provided an organic light emitting device including: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein at least one of the organic material layers comprises at least one compound represented by chemical formula 1.
Advantageous effects
The compound represented by chemical formula 1 may be used as a material of an organic material layer of an organic light emitting device, and may increase efficiency, achieve a low driving voltage, and/or improve lifetime characteristics in the organic light emitting device. In particular, the compound represented by chemical formula 1 may be used as a material for hole injection, hole transport, light emission, electron transport, and/or electron injection.
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 injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, 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.
In the present disclosure, a compound represented by chemical formula 1 is provided.
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; alkylthio; arylthio; an alkylsulfonyl group; arylsulfonyl; a silyl group; a boron base; an alkyl group; cycloalkyl; alkenyl groups; an aryl group; an aralkyl group; aralkenyl; alkylaryl groups; an alkylamino group; an aralkylamine group; heteroaryl amine groups; an arylamine group; aryl phosphino; and heteroaryl groups comprising at least one of N, O and S atoms, or substituted with substituents that are unsubstituted or linked with two or more of the substituents exemplified above. For example, a "substituent in which two or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl, or it may also be interpreted as a substituent to which two phenyl groups are linked.
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 substituent having the following structural formula, but is not limited thereto.
In the present disclosure, the ester group may have a structure in which 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 substituent 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 substituent having the following structural formula, but is not limited thereto.
In the present disclosure, the silyl group specifically includes, but is not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, and the like.
In the present disclosure, the boron group specifically includes trimethylboron group, triethylboron group, t-butyldimethylboroyl group, triphenylboron group, and 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 alkyl group has a carbon number of 1 to 20. According to another embodiment, the alkyl group has a carbon number of 1 to 10. According to another embodiment, the alkyl group has a carbon number of 1 to 6. Specific examples of the alkyl group include, but are not limited to, 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, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.
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 alkenyl group has a carbon number of 2 to 20. According to another embodiment, the alkenyl group has a carbon number of 2 to 10. According to yet another embodiment, the alkenyl group has a carbon number of 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- (naphthalen-1-yl) vinyl-1-yl, 2-bis (diphenyl-1-yl) vinyl-1-yl, 
Radical, styryl, etc., but is 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 cycloalkyl group has a carbon number of 3 to 30. According to another embodiment, the cycloalkyl group has a carbon number of 3 to 20. According to yet another embodiment, the cycloalkyl group has a carbon number of 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-t-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.
In the present disclosure, the aryl group is not particularly limited, but the carbon number thereof is preferably 6 to 60, and it may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has a carbon number of 6 to 30. According to one embodiment, the aryl group has a carbon number of 6 to 20. As the monocyclic aryl group, an aryl group may be phenyl, biphenyl, terphenyl, or the like, but is not limited thereto. Polycyclic aryl groups include naphthyl, anthryl, phenanthryl, pyrenyl,
Base, & gt>
A radical, a fluorenyl radical, etc., but is not limited thereto.
In the present disclosure, the fluorenyl group may be substituted, and two substituents may be linked to each other to form a spiro structure. In the case where the fluorenyl group is substituted, it may be formed 
Etc. However, the structure is not limited thereto.
In the present disclosure, the heteroaryl group is a heteroaryl group including 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. According to one exemplary embodiment, the heteroaryl group has 6 to 30 carbon atoms. According to one exemplary embodiment, the heteroaryl group has 6 to 20 carbon atoms. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl,
Azolyl, (-) -and (II) radicals>
Diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, and quinolylOxinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo->
Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthrolinyl, and i ∈ ->
Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but are not limited thereto.
In the present disclosure, the aryl groups in the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group are the same as the foregoing examples of the aryl groups. In the present disclosure, the alkyl groups in the aralkyl group, alkylaryl group, and alkylamino group are the same as the aforementioned examples of the alkyl group. In the present disclosure, heteroaryl groups in heteroaryl amines may employ the foregoing description of heteroaryl groups. In the present disclosure, alkenyl groups in aralkenyl groups are the same as the aforementioned examples of alkenyl groups. In the present disclosure, the foregoing description of aryl groups may be applied, except that arylene groups are divalent groups. In the present disclosure, the foregoing description of heteroaryl groups may be applied, except that the heteroarylene group is a divalent group. In the present disclosure, the foregoing description of 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 present disclosure, the foregoing description of heteroaryl groups may be applied, except that the heterocycle is not a monovalent group but is formed by combining two substituents.
Preferably, chemical formula 1 may be represented by any one of the following chemical formulas 1-1 to 1-4:
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
[ chemical formulas 1-4]
In chemical formulas 1-1 to 1-4,
R 1 、R 2 、L 1 d and n are as defined in chemical formula 1.
Preferably L 1 May be a single bond; substituted or unsubstituted C 6-20 Arylene groups; or substituted or unsubstituted C comprising at least one selected from N, O and S 2-20 Heteroarylene group.
More preferably L 1 May be a single bond, phenylene, biphenyldiyl, or naphthalenediyl.
Most preferably L 1 May be a single bond or any one selected from the following:
preferably Ar 1 And Ar is a group 2 May each independently be a substituted or unsubstituted C 6-20 An aryl group; or substituted or unsubstituted C comprising at least one selected from N, O and S 2-20 Heteroaryl groups.
More preferably Ar 1 And Ar is a group 2 May each independently be phenyl, biphenyl, naphthyl, phenanthryl, dibenzofuranyl, or dibenzothienyl.
Most preferably Ar 1 And Ar is a group 2 Can each independently be any one selected from the following：
Preferably Ar 3 And Ar is a group 4 May each independently be a substituted or unsubstituted C 6-20 An aryl group; or substituted or unsubstituted C comprising at least one selected from N, O and S 2-20 Heteroaryl groups.
More preferably Ar 3 And Ar is a group 4 May each independently be phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, dibenzofuranyl, dibenzothienyl, phenylcarbazolyl, or phenylnaphthyl.
Most preferably Ar 3 And Ar is a group 4 May each independently be any one selected from the group consisting of:
preferably L 2 And L 3 Each independently may be a single bond; or C which is substituted or unsubstituted 6-20 Arylene groups.
More preferably L 2 And L 3 May each independently be a single bond, phenylene, or naphthalenediyl.
Most preferably L 2 And L 3 May each independently be a single bond or any one selected from the group consisting of:
preferably L 4 And L 5 Each independently may be a single bond; substituted or unsubstituted C 6-20 Arylene groups; or substituted or unsubstituted C comprising at least one selected from N, O and S 2-20 Heteroarylene group.
More preferably L 4 And L 5 Can each independently be a single bond, a sub-groupPhenyl, biphenyldiyl, naphthalenediyl, or carbazolediyl.
Most preferably L 4 And L 5 May each independently be a single bond or any one selected from the group consisting of:
preferably Ar 1 And Ar is a group 2 At least one of which may be substituted or unsubstituted C 6-60 Aryl, more preferably Ar 1 And Ar is a group 2 At least one of which may be substituted or unsubstituted C 6-20 Aryl, more preferably Ar 1 And Ar is a group 2 At least one of which may be unsubstituted C 6-20 Aryl, and most preferably Ar 1 And Ar is a group 2 At least one of which may be phenyl or naphthyl.
Preferably Ar 3 And Ar is a group 4 At least one of which may be substituted or unsubstituted C 6-60 Aryl, more preferably Ar 3 And Ar is a group 4 At least one of which may be substituted or unsubstituted C 6-20 Aryl, more preferably Ar 3 And Ar is a group 4 At least one of which may be unsubstituted C 6-20 Aryl, and most preferably Ar 3 And Ar is a group 4 At least one of which may be phenyl, biphenyl, or naphthyl.
At the same time, R 2 Is a substituent of ring A.
Preferably, R 2 May be substituted or unsubstituted C 6-20 An aryl group; or substituted or unsubstituted C comprising at least one selected from N, O and S 2-20 Heteroaryl groups.
More preferably, R 2 May be phenyl, biphenyl, naphthyl, dibenzofuranyl, or dibenzothienyl.
Most preferably, R 2 May be any one selected from the following:
preferably, n may be 0.
Representative examples of the compound represented by chemical formula 1 are as follows:
l in chemical formula 1 1 Is a single bond and R 1 Is that
The compound of (2) can be prepared by a preparation method as shown in the following reaction scheme 1. Some compounds may be prepared by the preparation methods as shown in reaction scheme 2 below, and other compounds may be similarly prepared.
In schemes 1 and 2, R 1 、R 2 、L 1 、L 4 、L 5 、Ar 3 And Ar is a group 4 As defined in chemical formula 1 above, and X 1 And X 2 Each independently is halogen and preferably is chlorine or bromine.
Further, an organic light emitting device including the compound represented by chemical formula 1 above is provided. As one example, there is provided an organic light emitting device, including: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein at least one of the organic material layers comprises at least one compound represented by chemical formula 1.
The organic material layer of the organic light emitting device of the present disclosure may have a single layer structure, or it may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present disclosure may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto, and it may include a smaller number of organic material layers.
Further, the organic material layer may include an electron blocking layer or a light emitting layer, and the electron blocking layer or the light emitting layer may include a compound represented by chemical formula 1.
Further, the organic light emitting device according to the present disclosure may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. Further, the organic light emitting device according to the present disclosure may be an inverted organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light emitting device according to one embodiment of the present disclosure is illustrated in fig. 1 and 2.
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 injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a cathode 4. In such a structure, the compound represented by chemical formula 1 may be contained in the light emitting layer or the electron blocking layer.
The organic light emitting device according to the present disclosure may be manufactured by materials and methods known in the art, except that one or more of the organic material layers include a compound represented by chemical formula 1. In addition, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
For example, an organic light emitting device according to the present disclosure may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light emitting device may be manufactured by: a metal, a metal oxide having conductivity, or an alloy thereof is deposited on a substrate using a PVD (physical vapor deposition) method such as a sputtering method or an electron beam evaporation method to form an anode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and then a material that can function as a cathode is deposited on the organic material layer. In addition to such a method, the organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
In addition, in manufacturing an organic light emitting device, the compound represented by chemical formula 1 may be formed into an organic layer by a solution coating method and a vacuum deposition method. Here, the solution coating method means spin coating, dip coating, knife coating, ink jet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
In addition to such a method, the organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (international publication WO 2003/012890). However, the preparation method is not limited thereto.
As one example, the first electrode is an anode and the second electrode is a cathode, or alternatively, the first electrode is a cathode and the second electrode is an anode.
As the anode material, in general, a material having a large work function is preferably used so that holes can be smoothly injected into the organic material layer. Specific examples of anode materials include metals such as vanadiumChromium, 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 SnO 2 Sb; conductive polymers, e.g. poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene ](PEDOT), polypyrrole and polyaniline; etc., but is not limited thereto.
As the cathode material, in general, a material having a small work function is preferably used 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; multilayer structural materials, e.g. LiF/Al or LiO 2 Al; etc., but is not limited thereto.
The hole injection layer is a layer for injecting holes from the electrode, and the hole injection material is preferably a compound of: it has a capability of transporting holes, and thus has an effect of injecting holes in an anode, and has an excellent hole injection effect to a light emitting layer or a light emitting material, prevents excitons generated in the light emitting layer from moving to an electron injection layer or an electron injection material, and is excellent in the capability of forming a thin film. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably 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, hexanitrile hexaazabenzophenanthrene-based organic material, quinacridone-based organic material, and aryl amine-based organic material 
But not limited to, anthraquinone, polyaniline-based and polythiophene-based conductive polymers, etc.
The hole transport layer is a layer that receives holes from 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 transfer the holes to the light emitting layer. Specific examples thereof include an arylamine-based organic material, a conductive polymer, a block copolymer in which a conjugated moiety and a non-conjugated moiety are simultaneously present, and the like, but are not limited thereto.
The electron blocking layer is a layer placed between the hole transport layer and the light emitting layer to prevent electrons injected from the cathode from being transferred to the hole transport layer without being recombined in the light emitting layer, and is also referred to as an electron suppressing layer. For the electron blocking layer, a material having an electron affinity lower than that of the electron transport layer is preferable. Preferably, the material represented by chemical formula 1 of the present disclosure may be used as an electron blocking material.
The light emitting material is suitably a material capable of emitting light in the visible light region by receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, so as to combine them, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include 8-hydroxy-quinoline aluminum complex (Alq 3 ) The method comprises the steps of carrying out a first treatment on the surface of the Carbazole-based compounds; a dimeric styryl compound; BAlq; 10-hydroxybenzoquinoline-metal compounds; based on benzo
Oxazole, benzothiazole-based and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) based polymers; a spiro compound; polyfluorene; rubrene; etc., but is not limited thereto.
In particular, the light emitting layer may include a host material and a dopant material. The host material may be a fused aromatic ring derivative, a heterocyclic ring-containing compound, or the like. Specific examples of the condensed aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like. Examples of the heterocycle-containing compound include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto. Preferably, the material represented by chemical formula 1 of the present disclosure may be used as a host material, and one or more materials represented by chemical formula 1 may be included as a host material. Preferably, when two types of compounds represented by chemical formula 1 are used in the light emitting layer, the weight ratio thereof is 10:90 to 90:10, and more preferably 20:80 to 80:20, 30:70 to 70:30, or 40:60 to 60:40.
Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivative is a substituted or unsubstituted fused aromatic ring derivative having an arylamino group, and examples thereof include pyrene, anthracene having an arylamino group,
Bisindenopyrene, and the like. Styrylamine compounds are compounds 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 aryl, silyl, alkyl, cycloalkyl, and arylamino groups are substituted or unsubstituted. Specific examples thereof include styrylamine, styrylenediamine, styrylenetriamine, styrylenetetramine, and the like, but are not limited thereto. Further, the metal complex includes iridium complex, platinum complex, and the like, but is not limited thereto.
For example, at least one selected from the following may be used as the dopant material, but the present disclosure is not limited thereto:
the hole blocking layer is a layer placed between the electron transport layer and the light emitting layer to prevent holes injected from the anode from being transferred to the electron transport layer without being recombined in the light emitting layer, and is also referred to as a hole suppressing layer. For the hole blocking layer, a material having high ionization energy is preferable.
Electron transportThe transport layer is a layer that receives electrons from the electron injection layer and transmits the electrons to the light emitting layer. As the electron transporting material, a material that can well receive electrons from the cathode and transfer the electrons to the light emitting layer, and that has a large electron mobility is suitable. Examples thereof include Al complexes of 8-hydroxyquinoline; comprising Alq 3 Is a complex of (a) and (b); an organic radical compound; hydroxyflavone-metal complexes; etc., but is not limited thereto. The electron transport layer may be used with any desired cathode material as used according to the related art. In particular, suitable examples of cathode materials are typical materials having a low work function followed by an aluminum layer or a silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.
The electron injection layer is a layer that injects electrons from an electrode, and is preferably a compound that: 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 by the light emitting layer from moving to a hole injecting layer, and is also excellent in an ability to form a thin film. Specific examples thereof include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, 
Azole,/->
Diazole, triazole, imidazole, < >>
Tetracarboxylic acid, fluorenylmethane, anthrone, and the like, and derivatives thereof; a metal complex compound; a nitrogen-containing 5-membered ring derivative; etc., but is not limited thereto.
Examples of the metal complex compound include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (2-methyl-8-quinoline) chlorogallium, gallium bis (2-methyl-8-quinoline) (o-cresol), aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol), and the like.
Meanwhile, as used herein, an "electron injection and transport layer" is a layer performing the function of both an electron injection layer and an electron transport layer, and materials for the respective layers may be used alone or in combination, but the present disclosure is not limited thereto.
The organic light emitting device according to the present disclosure may be a bottom emission device, a top emission device, or a double-sided emission device, and in particular, may be a bottom emission device requiring relatively high light emitting efficiency.
In addition, the compound represented by chemical formula 1 may be contained in an organic solar cell or an organic transistor in addition to the organic light emitting device.
The preparation of the compound represented by chemical formula 1 and the organic light emitting device including the same will be described in detail in the following examples. However, these embodiments are presented for illustrative purposes only and are not intended to limit the scope of the present disclosure.
Preparation example
PREPARATION EXAMPLE 1-1
To 300ml of THF were added compound AA (15 g,53.9 mmol) and [1,1' -biphenyl ] -4-ylboronic acid (10.7 g,53.9 mmol) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g,161.8 mmol) was dissolved in 67ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 10 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.4g of compound sub aa-1 (yield 63%, MS: [ m+h ] +=396).
300ml of 1, 4-di-under nitrogen
To the alkane were added the compound sub AA-1 (15 g,37.9 mmol) and bis (pinacolato) diboron (10.6 g,41.7 mmol) and the mixture was stirred and refluxed. Then, potassium acetate (5.6 g,56.8 mmol) was added and stirred well, followed by bis (dibenzylideneacetone) palladium (0) (0.7 g,1.1 mmol) and tricyclohexylphosphine (0.6 g,2.3 mmol). After 8 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated using chloroform and water, and distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.4g of compound sub AA-2 (yield 67%, MS: [ M+H)]+＝488)。
To 300ml of THF were added the compound sub AA-2 (15 g,30.8 mmol) and Trz1 (9.8 g,30.8 mmol) under nitrogen, and the mixture was stirred and refluxed. Then, potassium carbonate (12.8 g,92.3 mmol) was dissolved in 38ml of water, and then added thereto. After this time, it was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was then added. After 12 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.9g of compound 1-1 (yield 60%, MS: [ m+h ] +=643).
PREPARATION EXAMPLES 1-2
To 300ml of THF were added compound AB (15 g,53.9 mmol) and phenylboronic acid (6.6 g,53.9 mmol) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g,161.8 mmol) was dissolved in 67ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 9 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.4g of compound subeb-1 (yield 78%, MS: [ m+h ] +=320).
300ml of 1, 4-di-under nitrogen
To the alkane were added the compound subeb-1 (15 g,46.9 mmol) and bis (pinacolato) diboron (13.1 g,51.6 mmol) and the mixture was stirred and refluxed. Then, potassium acetate (6.9 g,70.4 mmol) was added and stirred well, followed by bis (dibenzylideneacetone) palladium (0) (0.8 g,1.4 mmol) and tricyclohexylphosphine (0.8 g,2.8 mmol). After 9 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated using chloroform and water, and distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was subjected to reduced pressure And (5) distilling. The concentrated compound was purified by silica gel column chromatography to prepare 14.3g of compound subeb-2 (yield 74%, MS: [ m+h)]+＝412)。
To 300ml of THF were added the compounds subeb-2 (15 g,36.5 mmol) and Trz2 (9.8 g,36.5 mmol) under nitrogen, and the mixture was stirred and refluxed. Then, potassium carbonate (15.1 g,109.4 mmol) was dissolved in 45ml of water and then added thereto. After this time, it was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was then added. After 9 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.4g of compound 1-2 (yield 66%, MS: [ m+h ] +=517).
Preparation examples 1 to 3
To 300ml of THF were added compound AE (15 g,53.9 mmol) and phenylboronic acid (6.6 g,53.9 mmol) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g,161.8 mmol) was dissolved in 67ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 8 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 10.7g of compound sub ae-1 (yield 62%, MS: [ m+h ] +=320).
To 300ml of THF were added the compounds sub AE-1 (15 g,46.9 mmol) and Trz3 (22.5 g,46.9 mmol) under nitrogen and the mixture was stirred and refluxed. Then, potassium carbonate (19.5 g,140.7 mmol) was dissolved in 58ml of water and then added thereto. After this time, it was stirred well and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.5 mmol) was then added. After 9 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 25.3g of the compound 1-3 (yield 75%, MS: [ m+h ] +=719).
Preparation examples 1 to 4
To 300ml of THF were added the compounds sub AE-1 (15 g,46.9 mmol) and Trz4 (20.8 g,46.9 mmol) under nitrogen and the mixture was stirred and refluxed. Then, potassium carbonate (19.5 g,140.7 mmol) was dissolved in 58ml of water and then added thereto. After this time, it was stirred well and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.5 mmol) was then added. After 11 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 22.1g of compounds 1 to 4 (yield 69%, MS: [ m+h ] +=683).
Preparation examples 1 to 5
Compound AF (15 g,53.9 mmol) and naphthalen-2-ylboronic acid (9.3 g,53.9 mmol) were added to 300ml of THF under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g,161.8 mmol) was dissolved in 67ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 8 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.1g of compound sub af-1 (yield 66%, MS: [ m+h ] +=370).
To 300ml of THF were added the compound sub AF-1 (15 g,40.6 mmol) and Trz5 (16.4 g,40.6 mmol) under nitrogen, and the mixture was stirred and refluxed. Then, potassium carbonate (16.8 g,121.7 mmol) was dissolved in 50ml of water, and then added thereto. After this time, it was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was then added. After 12 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17.4g of compounds 1 to 5 (yield 62%, MS: [ m+h ] +=693).
Preparation examples 1 to 6
Compound BA (15 g,53.9 mmol) and phenylboronic acid (6.6 g,53.9 mmol) were added to 300ml THF under nitrogen and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g,161.8 mmol) was dissolved in 67ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 10 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.6g of compound subsba-1 (yield 79%, MS: [ m+h ] +=320).
300ml of 1, 4-di-under nitrogen
To the alkane were added the compound sub BA-1 (15 g,46.9 mmol) and bis (pinacolato) diboron (13.1 g,51.6 mmol) and the mixture was stirred and refluxed. Then, potassium acetate (6.9 g,70.4 mmol) was added and stirred well, followed by bis (dibenzylideneacetone) palladium (0) (0.8 g,1.4 mmol) and tricyclohexylphosphine (0.8 g,2.8 mmol). After 8 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated using chloroform and water, and distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.1g of compound subsba-2 (yield 68%, MS: [ m+h) ]+＝412)。
To 300ml of THF were added the compounds sub BA-2 (15 g,36.5 mmol) and Trz7 (14.4 g,36.5 mmol) under nitrogen and the mixture was stirred and refluxed. Then, potassium carbonate (15.1 g,109.4 mmol) was dissolved in 45ml of water and then added thereto. After this time, it was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was then added. After 8 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.5g of compounds 1 to 6 (yield 66%, MS: [ m+h ] +=643).
Preparation examples 1 to 7
To 300ml of THF were added compound BB (15 g,53.9 mmol) and phenylboronic acid (6.6 g,53.9 mmol) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g,161.8 mmol) was dissolved in 67ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 11 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.2g of compound subsbb-1 (yield 65%, MS: [ m+h ] +=320).
To 300ml of THF were added the compound sub BB-1 (15 g,46.9 mmol) and Trz8 (18.9 g,46.9 mmol) under nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (19.5 g,140.7 mmol) was dissolved in 58ml of water and then added thereto. After this time, it was stirred well and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.5 mmol) was then added. After 9 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18.1g of compounds 1 to 7 (yield 60%, MS: [ m+h ] +=643).
Preparation examples 1 to 8
To 300ml of THF were added under nitrogen the compound BE (15 g,53.9 mmol) and dibenzo [ b, d ] thiophen-1-ylboronic acid (12.3 g,53.9 mmol), and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g,161.8 mmol) was dissolved in 67ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 11 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16.7g of compound sube-1 (yield 73%, MS: [ m+h ] +=426).
To 300ml of THF were added the compounds sube-1 (15 g,35.2 mmol) and Trz9 (14.2 g,35.2 mmol) under nitrogen and the mixture was stirred and refluxed. Then, potassium carbonate (14.6 g,105.7 mmol) was dissolved in 44ml of water and then added thereto. After this time, it was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was then added. After 10 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18.2g of compounds 1 to 8 (yield 69%, MS: [ m+h ] +=749).
Preparation examples 1 to 9
To 300ml of THF were added under nitrogen the compound BF (15 g,53.9 mmol) and phenylboronic acid (6.6 g,53.9 mmol), and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g,161.8 mmol) was dissolved in 67ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 9 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 10.5g of compound subBF-1 (yield 61%, MS: [ m+h ] +=320).
To 300ml of THF were added the compound sub BF-1 (15 g,46.9 mmol) and Trz10 (22.5 g,46.9 mmol) under nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (19.5 g,140.7 mmol) was dissolved in 58ml of water and then added thereto. After this time, it was stirred well and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.5 mmol) was then added. After 11 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 20.2g of compounds 1 to 9 (yield 60%, MS: [ m+h ] +=719).
Preparation examples 1 to 10
To 300ml of THF were added compound CA (15 g,51 mmol) and phenylboronic acid (6.2 g,51 mmol) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g,153 mmol) was dissolved in 63ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 10 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 10.4g of a compound sub ca-1 (yield 61%, MS: [ m+h ] +=336).
To 300ml of THF were added the compound sub CA-1 (15 g,44.7 mmol) and Trz12 (19.2 g,44.7 mmol) under nitrogen and the mixture was stirred and refluxed. Then, potassium carbonate (18.5 g,134 mmol) was dissolved in 56ml of water and then added thereto. After this time, it was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was then added. After 8 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 20.5g of compounds 1 to 10 (yield 67%, MS: [ m+h ] +=685).
Preparation examples 1 to 11
To 300ml of THF were added compound CB (15 g,51 mmol) and phenylboronic acid (6.2 g,51 mmol) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g,153 mmol) was dissolved in 63ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 10 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.2g of a compound sub cb-1 (yield 77%, MS: [ m+h ] +=336).
300ml of 1, 4-di-under nitrogen
To the alkane were added the compound sub-cb-1 (15 g,44.7 mmol) and bis (pinacolato) diboron (12.5 g,49.1 mmol) and the mixture was stirred and refluxed. Then, potassium acetate (6.6 g,67 mmol) was added and stirred thoroughly, then bis (dibenzylideneacetone) palladium (0) (0.8 g,1.3 mmol) and tricyclohexylphosphine were added(0.8 g,2.7 mmol). After 9 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated using chloroform and water, and distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.9g of compound sub-CB-2 (yield 73%, MS: [ M+H)]+＝428)。
To 300ml of THF were added the compound sub-CB-2 (15 g,35.1 mmol) and Trz13 (13.8 g,35.1 mmol) under nitrogen, and the mixture was stirred and refluxed. Then, potassium carbonate (14.6 g,105.3 mmol) was dissolved in 44ml of water and then added thereto. After this time, it was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was then added. After 10 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16.6g of compounds 1 to 11 (yield 72%, MS: [ m+h ] +=659).
Preparation examples 1 to 12
To 300ml of THF were added the compound sub-CB-1 (15 g,36.5 mmol) and Trz14 (14.7 g,36.5 mmol) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (15.1 g,109.4 mmol) was dissolved in 45ml of water and then added thereto. After this time, it was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was then added. After 12 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17g of compounds 1 to 12 (yield 71%, MS: [ m+h ] +=659).
Preparation examples 1 to 13
To 300ml of THF were added compound CE (15 g,51 mmol) and dibenzo [ b, d ] furan-1-ylboronic acid (10.8 g,51 mmol) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g,153 mmol) was dissolved in 63ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 12 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.7g of a compound subCE-1 (yield 63%, MS: [ M+H ] +=426).
To 300ml of THF were added the compound sub-CE-1 (15 g,35.2 mmol) and Trz15 (12.4 g,35.2 mmol) under nitrogen, and the mixture was stirred and refluxed. Then, potassium carbonate (14.6 g,105.7 mmol) was dissolved in 44ml of water and then added thereto. After this time, it was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was then added. After 10 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.2g of compounds 1 to 13 (yield 62%, MS: [ m+h ] +=699).
Preparation examples 1 to 14
To 300ml of THF were added compound CF (15 g,51 mmol) and naphthalen-2-ylboronic acid (8.8 g,51 mmol) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g,153 mmol) was dissolved in 63ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 11 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.9g of a compound subCF-1 (yield 76%, MS: [ M+H ] +=386).
To 300ml of THF were added the compound sub CF-1 (15 g,38.9 mmol) and Trz5 (15.7 g,38.9 mmol) under nitrogen and the mixture was stirred and refluxed. Then, potassium carbonate (16.1 g,116.6 mmol) was dissolved in 48ml of water, and then added thereto. After this time, it was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was then added. After 12 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18.2g of compounds 1 to 14 (yield 66%, MS: [ m+h ] +=709).
Preparation examples 1 to 15
To 300ml of THF were added compound DA (15 g,51 mmol) and phenylboronic acid (6.2 g,51 mmol) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g,153 mmol) was dissolved in 63ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 12 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.6g of compound subDA-1 (yield 68%, MS: [ M+H ] +=336).
300ml of 1, 4-di-under nitrogen
To the alkane were added the compound sub DA-1 (15 g,44.7 mmol) and bis (pinacolato) diboron (12.5 g,49.1 mmol) and the mixture was stirred and refluxed. Then, potassium acetate (6.6 g,67 mmol) was added and stirred well, followed by bis (dibenzylideneacetone) palladium (0) (0.8 g,1.3 mmol) and tricyclohexylphosphine (0.8 g,2.7 mmol). After 7 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated using chloroform and water, and distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, and stirredStirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.4g of compound subDA-2 (yield 70%, MS: [ M+H ]]+＝428)。
To 300ml of THF were added the compound subDA-2 (15 g,35.1 mmol) and Trz17 (13.8 g,35.1 mmol) under nitrogen, and the mixture was stirred and refluxed. Then, potassium carbonate (14.6 g,105.3 mmol) was dissolved in 44ml of water and then added thereto. After this time, it was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was then added. After 11 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.6g of compounds 1 to 15 (yield 63%, MS: [ m+h ] + =659).
Preparation examples 1 to 16
To 300ml of THF were added compound DB (15 g,51 mmol) and naphthalene-2-yl-boronic acid (8.8 g,51 mmol) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g,153 mmol) was dissolved in 63ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 12 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.4g of compound subDB-1 (yield 68%, MS: [ M+H ] +=386).
300ml of 1, 4-di-under nitrogen
To the alkane were added the compound subDB-1 (15 g,39 mmol) and bis (pinacolato) diboron (10.9 g,42.9 mmol) and the mixture was stirred and refluxed. Then, potassium acetate (5.7 g,58.5 mmol) was added and stirred well, followed by bis (dibenzylideneacetone) palladium (0) (0.7 g,1.2 mmol) and tricyclohexylphosphine (0.7 g,2.3 mmol). After 7 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated using chloroform and water, and distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.9g of compound subDB-2 (yield 75%, MS: [ M+H) ]+＝478)。
To 300ml of THF were added the compounds subDB-2 (15 g,31.4 mmol) and Trz2 (8.4 g,31.4 mmol) under nitrogen and the mixture was stirred and refluxed. Then, potassium carbonate (13 g,94.3 mmol) was dissolved in 39ml of water and then added thereto. After this time, it was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was then added. After 11 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13g of compounds 1 to 16 (yield 71%, MS: [ m+h ] +=583).
Preparation examples 1 to 17
To 300ml of THF were added compound DF (15 g,51 mmol) and phenylboronic acid (6.2 g,51 mmol) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g,153 mmol) was dissolved in 63ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 9 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.1g of compound subDF-1 (yield 65%, MS: [ M+H ] +=336).
To 300ml of THF were added the compound subDF-1 (15 g,44.7 mmol) and Trz18 (18 g,44.7 mmol) under nitrogen and the mixture was stirred and refluxed. Then, potassium carbonate (18.5 g,134 mmol) was dissolved in 56ml of water and then added thereto. After this time, it was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was then added. After 12 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18.2g of compounds 1 to 17 (yield 62%, MS: [ m+h ] +=659).
PREPARATION EXAMPLE 2-1
Compound AA (15 g,53.9 mmol) and naphthalen-2-ylboronic acid (9.3 g,53.9 mmol) are added to 300ml THF under a nitrogen atmosphere and the mixture is stirred and refluxed. Then, potassium carbonate (22.4 g,161.8 mmol) was dissolved in 67ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 12 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.3g of compound sub aa-3 (yield 77%, MS: [ m+h ] +=370).
To 200ml of xylene under nitrogen was added compound sub AA-3 (10 g,27 mmol), compound amine 1 (9.1 g,27 mmol) and sodium tert-butoxide (8.6 g,40.6 mmol), and the mixture was stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.1 g,0.3 mmol) was added thereto. After 2 hours, the reaction was complete and after cooling to room temperature the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 10.8g of compound 2-1 (yield 60%, MS: [ m+h ] +=669).
PREPARATION EXAMPLE 2-2
To 200ml of xylene under nitrogen was added compound sub AB-1 (10 g,31.3 mmol), compound amine 2 (9.2 g,31.3 mmol) and sodium tert-butoxide (10 g,46.9 mmol), and the mixture was stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was added thereto. After 2 hours, the reaction was complete and after cooling to room temperature the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.9g of compound 2-2 (yield 66%, MS: [ m+h ] +=579).
PREPARATION EXAMPLES 2-3
Compound AC (15 g,53.9 mmol) and phenylboronic acid (6.6 g,53.9 mmol) were added to 300ml THF under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g,161.8 mmol) was dissolved in 67ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 9 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.1g of compound subarc-1 (yield 76%, MS: [ m+h ] +=320).
To 200ml of xylene under nitrogen was added compound sub AC-1 (10 g,31.3 mmol), compound amine 3 (12.8 g,31.3 mmol) and sodium tert-butoxide (10 g,46.9 mmol), and the mixture was stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was added thereto. After 3 hours, the reaction was complete and after cooling to room temperature the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15g of compound 2-3 (yield 69%, MS: [ m+h ] +=694).
PREPARATION EXAMPLES 2 to 4
To 300ml of THF were added under nitrogen compound subarc-1 (15 g,46.9 mmol) and compound amine 4 (22.8 g,46.9 mmol), and the mixture was stirred and refluxed. Then, potassium carbonate (19.5 g,140.7 mmol) was dissolved in 58ml of water and then added thereto. After this time, it was stirred well and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.5 mmol) was then added. After 10 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 23.1g of compound 2-4 (yield 68%, MS: [ m+h ] +=725).
PREPARATION EXAMPLES 2 to 5
To 300ml of THF were added compound AE (15 g,53.9 mmol) and [1,1' -biphenyl ] -4-ylboronic acid (10.7 g,53.9 mmol) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g,161.8 mmol) was dissolved in 67ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 12 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17g of compound sub ae-2 (yield 80%, MS: [ m+h ] +=396).
To 200ml of xylene under nitrogen was added compound sub AE-2 (10 g,25.3 mmol), compound amine 5 (7.5 g,25.3 mmol) and sodium tert-butoxide (8 g,37.9 mmol), and the mixture was stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.1 g,0.3 mmol) was added thereto. After 2 hours, the reaction was complete and after cooling to room temperature the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 8.3g of compound 2-5 (yield 50%, MS: [ m+h ] +=655).
Preparation examples 2 to 6
Compound AF (15 g,53.9 mmol) and phenylboronic acid (6.6 g,53.9 mmol) were added to 300ml THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g,161.8 mmol) was dissolved in 67ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 8 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.7g of compound sub af-2 (yield 74%, MS: [ m+h ] +=320).
To 300ml of THF were added under nitrogen compound sub AF-2 (15 g,46.9 mmol) and compound amine 6 (20.7 g,46.9 mmol), and the mixture was stirred and refluxed. Then, potassium carbonate (19.5 g,140.7 mmol) was dissolved in 58ml of water and then added thereto. After this time, it was stirred well and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.5 mmol) was then added. After 8 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 20.1g of compound 2-6 (yield 63%, MS: [ m+h ] +=681).
Preparation examples 2 to 7
To 300ml of THF were added compound sub BA-1 (15 g,46.9 mmol) and compound amine 10 (18.5 g,46.9 mmol) under nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (19.5 g,140.7 mmol) was dissolved in 58ml of water and then added thereto. After this time, it was stirred well and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.5 mmol) was then added. After 10 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 23.2g of compound 2-7 (yield 78%, MS: [ m+h ] +=635).
Preparation examples 2 to 8
To 300ml of THF were added compound sub BB-1 (15 g,46.9 mmol) and compound amine 11 (23.1 g,46.9 mmol) under nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (19.5 g,140.7 mmol) was dissolved in 58ml of water and then added thereto. After this time, it was stirred well and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.5 mmol) was then added. After 12 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 26.7g of compound 2-8 (yield 78%, MS: [ m+h ] +=731).
Preparation examples 2 to 9
To 200ml of xylene under nitrogen was added compound sub BB-1 (10 g,31.3 mmol), compound amine 12 (13.3 g,31.3 mmol) and sodium t-butoxide (10 g,46.9 mmol), and the mixture was stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was added thereto. After 3 hours, the reaction was complete and after cooling to room temperature the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.2g of compound 2-9 (yield 60%, MS: [ m+h ] +=703).
Preparation examples 2 to 10
To 300ml of THF were added compound BC (15 g,53.9 mmol) and naphthalene-2-yl-boronic acid (9.3 g,53.9 mmol) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g,161.8 mmol) was dissolved in 67ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 11 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.1g of compound subBC-1 (yield 76%, MS: [ m+h ] +=370).
To 200ml of xylene under nitrogen was added compound sub BC-1 (10 g,27 mmol), compound amine 13 (8.7 g,27 mmol) and sodium tert-butoxide (8.6 g,40.6 mmol), and the mixture was stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.1 g,0.3 mmol) was added thereto. After 3 hours, the reaction was complete and after cooling to room temperature the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 9g of compound 2-10 (yield 51%, MS: [ m+h ] +=655).
PREPARATION EXAMPLES 2 to 11
To 300ml of THF were added compound BC (15 g,53.9 mmol) and phenylboronic acid (6.6 g,53.9 mmol) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g,161.8 mmol) was dissolved in 67ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 11 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.4g of compound subBC-2 (yield 78%, MS: [ m+h ] +=320).
To 300ml of THF were added the compound sub BC-2 (15 g,46.9 mmol) and the compound amine 14 (17.8 g,46.9 mmol) under nitrogen, and the mixture was stirred and refluxed. Then, potassium carbonate (19.5 g,140.7 mmol) was dissolved in 58ml of water and then added thereto. After this time, it was stirred well and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.5 mmol) was then added. After 10 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 21.5g of compound 2-11 (yield 74%, MS: [ m+h ] +=619).
PREPARATION EXAMPLES 2 to 12
To 300ml of THF were added compound BC (15 g,53.9 mmol) and dibenzo [ b, d ] furan-1-ylboronic acid (11.4 g,53.9 mmol) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g,161.8 mmol) was dissolved in 67ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 9 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.9g of compound subBC-3 (yield 63%, MS: [ m+h ] +=410).
To 300ml of THF were added the compound sub BC-3 (15 g,36.6 mmol) and the compound amine 15 (16.2 g,36.6 mmol) under nitrogen, and the mixture was stirred and refluxed. Then, potassium carbonate (15.2 g,109.8 mmol) was dissolved in 46ml of water and then added thereto. After this time, it was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was then added. After 12 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18.3g of compound 2-12 (yield 65%, MS: [ m+h ] +=771).
PREPARATION EXAMPLES 2 to 13
To 300ml of THF were added compound BE (15 g,53.9 mmol) and phenylboronic acid (6.6 g,53.9 mmol) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g,161.8 mmol) was dissolved in 67ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 12 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.1g of compound sube-2 (yield 76%, MS: [ m+h ] +=320).
To 200ml of xylene under nitrogen atmosphere were added compound sube-2 (10 g,31.3 mmol), compound amine 16 (10.8 g,31.3 mmol) and sodium tert-butoxide (10 g,46.9 mmol), and the mixture was stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was added thereto. After 2 hours, the reaction was complete and after cooling to room temperature the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13g of compound 2-13 (yield 66%, MS: [ m+h ] +=629).
PREPARATION EXAMPLES 2 to 14
To 300ml of THF were added under nitrogen the compound sube-2 (15 g,46.9 mmol) and the compound amine 17 (21.4 g,46.9 mmol), and the mixture was stirred and refluxed. Then, potassium carbonate (19.5 g,140.7 mmol) was dissolved in 58ml of water and then added thereto. After this time, it was stirred well and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.5 mmol) was then added. After 10 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 23.4g of compound 2-14 (yield 72%, MS: [ m+h ] +=695).
PREPARATION EXAMPLES 2 to 15
To 300ml of THF were added under nitrogen the compound sub BF-1 (15 g,46.9 mmol) and the compound amine 18 (22.1 g,46.9 mmol), and the mixture was stirred and refluxed. Then, potassium carbonate (19.5 g,140.7 mmol) was dissolved in 58ml of water and then added thereto. After this time, it was stirred well and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.5 mmol) was then added. After 8 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 23.3g of compound 2-15 (yield 70%, MS: [ m+h ] +=711).
PREPARATION EXAMPLES 2 to 16
To 300ml of THF were added compound CA (15 g,51 mmol) and dibenzo [ b, d ] thiophen-3-ylboronic acid (11.6 g,51 mmol) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g,153 mmol) was dissolved in 63ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 9 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.4g of a compound of subCA-2 (yield 64%, MS: [ M+H ] +=442).
To 300ml of THF were added the compound sub CA-2 (15 g,33.9 mmol) and the compound amine 22 (14.1 g,33.9 mmol) under nitrogen, and the mixture was stirred and refluxed. Then, potassium carbonate (14.1 g,101.8 mmol) was dissolved in 42ml of water, and then added thereto. After this time, it was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was then added. After 8 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 20.8g of compound 2-16 (yield 79%, MS: [ m+h ] +=777).
PREPARATION EXAMPLES 2 to 17
To 200ml of xylene under nitrogen was added the compound sub-cb-1 (10 g,29.8 mmol), the compound amine 23 (12.6 g,29.8 mmol) and sodium tert-butoxide (9.5 g,44.7 mmol), and the mixture was stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was added thereto. After 3 hours, the reaction was complete and after cooling to room temperature the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.5g of compound 2-17 (yield 58%, MS: [ m+h ] +=722).
PREPARATION EXAMPLES 2 to 18
To 300ml of THF were added the compound sub-CB-1 (15 g,44.7 mmol) and the compound amine 24 (21.1 g,44.7 mmol) under nitrogen, and the mixture was stirred and refluxed. Then, potassium carbonate (18.5 g,134 mmol) was dissolved in 56ml of water and then added thereto. After this time, it was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was then added. After 9 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 20.1g of compound 2-18 (yield 62%, MS: [ m+h ] +=727).
PREPARATION EXAMPLES 2 to 19
Compound CC (15 g,51 mmol) and phenylboronic acid (6.2 g,51 mmol) are added to 300ml THF under nitrogen and the mixture is stirred and refluxed. Then, potassium carbonate (21.1 g,153 mmol) was dissolved in 63ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 8 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 10.9g of a compound of subCC-1 (yield 64%, MS: [ m+h ] +=336).
To 200ml of xylene under nitrogen was added the compound sub-C-1 (10 g,29.8 mmol), the compound amine 25 (12.3 g,29.8 mmol) and sodium tert-butoxide (9.5 g,44.7 mmol), and the mixture was stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was added thereto. After 3 hours, the reaction was complete and after cooling to room temperature the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14g of compounds 2 to 19 (yield 66%, MS: [ m+h ] +=711).
PREPARATION EXAMPLES 2 to 20
To 200ml of xylene under nitrogen was added the compound sub-C-1 (10 g,29.8 mmol), the compound amine 26 (11.1 g,29.8 mmol) and sodium tert-butoxide (9.5 g,44.7 mmol), and the mixture was stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was added thereto. After 3 hours, the reaction was complete and after cooling to room temperature the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12g of compound 2-20 (yield 60%, MS: [ m+h ] +=671).
PREPARATION EXAMPLES 2 to 21
To 200ml of xylene under nitrogen was added the compound sub-C-1 (10 g,29.8 mmol), the compound amine 27 (14.6 g,29.8 mmol) and sodium tert-butoxide (9.5 g,44.7 mmol), and the mixture was stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was added thereto. After 3 hours, the reaction was complete and after cooling to room temperature the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.8g of compound 2-21 (yield 53%, MS: [ m+h ] +=747).
PREPARATION EXAMPLES 2 to 22
Compound CD (15 g,51 mmol) and phenylboronic acid (6.2 g,51 mmol) were added to 300ml THF under a nitrogen atmosphere and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g,153 mmol) was dissolved in 63ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 10 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.8g of a compound sub cd-1 (yield 75%, MS: [ m+h ] +=336).
To 300ml of THF were added the compound sub CD-1 (15 g,44.7 mmol) and the compound amine 28 (19.7 g,44.7 mmol) under nitrogen, and the mixture was stirred and refluxed. Then, potassium carbonate (18.5 g,134 mmol) was dissolved in 56ml of water and then added thereto. After this time, it was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was then added. After 11 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 20.2g of compound 2-22 (yield 65%, MS: [ m+h ] +=697).
PREPARATION EXAMPLES 2 to 23
To 300ml of THF were added compound CE (15 g,51 mmol) and phenylboronic acid (6.2 g,51 mmol) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g,153 mmol) was dissolved in 63ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 12 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.5g of a compound subCE-2 (yield 79%, MS: [ m+h ] +=336).
To 200ml of xylene under nitrogen was added the compound sub-ce-2 (10 g,29.8 mmol), the compound amine 29 (10.3 g,29.8 mmol) and sodium tert-butoxide (9.5 g,44.7 mmol), and the mixture was stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was added thereto. After 2 hours, the reaction was complete and after cooling to room temperature the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.9g of compound 2-23 (yield 62%, MS: [ m+h ] +=645).
PREPARATION EXAMPLES 2 to 24
To 300ml of THF were added compound CF (15 g,51 mmol) and phenylboronic acid (6.2 g,51 mmol) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g,153 mmol) was dissolved in 63ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 9 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.6g of a compound of subCF-2 (yield 68%, MS: [ M+H ] +=336).
To 200ml of xylene under nitrogen was added the compound sub cf-2 (10 g,29.8 mmol), the compound amine 30 (10.5 g,29.8 mmol) and sodium tert-butoxide (9.5 g,44.7 mmol), and the mixture was stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was added thereto. After 3 hours, the reaction was completed, and after cooling to room temperature, the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.4g of compound 2-24 (yield 64%, MS: [ m+h ] + =651).
PREPARATION EXAMPLES 2 to 25
To 300ml of THF were added under nitrogen the compound subDB-1 (15 g,38.9 mmol) and the compound amine 33 (17.2 g,38.9 mmol), and the mixture was stirred and refluxed. Then, potassium carbonate (16.1 g,116.6 mmol) was dissolved in 48ml of water, and then added thereto. After this time, it was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was then added. After 8 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 21.2g of compound 2-25 (yield 73%, MS: [ m+h ] +=747).
PREPARATION EXAMPLES 2 to 26
To 300ml of THF were added compound DB (15 g,51 mmol) and phenylboronic acid (6.2 g,51 mmol) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g,153 mmol) was dissolved in 63ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 10 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.2g of compound subDB-2 (yield 77%, MS: [ M+H ] +=336).
To 200ml of xylene under nitrogen atmosphere were added compound subDB-2 (10 g,31.3 mmol), compound amine 34 (12.9 g,31.3 mmol) and sodium tert-butoxide (10 g,46.9 mmol), and the mixture was stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was added thereto. After 2 hours, the reaction was complete and after cooling to room temperature the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15g of compounds 2 to 26 (yield 69%, MS: [ m+h ] +=695).
PREPARATION EXAMPLES 2 to 27
To 300ml of THF were added compound DC (15 g,51 mmol) and naphthalene-2-ylboronic acid (8.8 g,51 mmol) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g,153 mmol) was dissolved in 63ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 8 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.8g of compound subDC-1 (yield 65%, MS: [ m+h ] +=386).
To 200ml of xylene under nitrogen atmosphere were added compound subDC-1 (10 g,25.9 mmol), compound amine 13 (8.3 g,25.9 mmol) and sodium tert-butoxide (8.3 g,38.9 mmol), and the mixture was stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.1 g,0.3 mmol) was added thereto. After 2 hours, the reaction was complete and after cooling to room temperature the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 10.9g of compound 2-27 (yield 63%, MS: [ m+h ] +=671).
PREPARATION EXAMPLES 2 to 28
To 300ml of THF were added compound DC (15 g,51 mmol) and phenylboronic acid (6.2 g,51 mmol) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g,153 mmol) was dissolved in 63ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 12 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.1g of compound subDC-2 (yield 65%, MS: [ m+h ] +=336).
To 300ml of THF were added under nitrogen the compound sub DC-2 (15 g,44.7 mmol) and the compound amine 7 (21 g,44.7 mmol), and the mixture was stirred and refluxed. Then, potassium carbonate (18.5 g,134 mmol) was dissolved in 56ml of water and then added thereto. After this time, it was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was then added. After 8 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 21g of compounds 2 to 28 (yield 65%, MS: [ m+h ] +=725).
PREPARATION EXAMPLES 2 to 29
To 300ml of THF were added compound DE (15 g,51 mmol) and dibenzo [ b, d ] furan-2-ylboronic acid (10.8 g,51 mmol) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g,153 mmol) was dissolved in 63ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 12 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16g of compound sub-1 (yield 74%, MS: [ m+h ] + =426).
To 300ml of THF were added under nitrogen the compound sub DE-1 (15 g,35.2 mmol) and the compound amine 35 (17.3 g,35.2 mmol) and the mixture was stirred and refluxed. Then, potassium carbonate (14.6 g,105.7 mmol) was dissolved in 44ml of water and then added thereto. After this time, it was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was then added. After 9 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 19.7g of compounds 2 to 29 (yield 67%, MS: [ m+h ] +=837).
PREPARATION EXAMPLES 2 to 30
To 300ml of THF were added compound DF (15 g,51 mmol) and [1,1' -biphenyl ] -4-ylboronic acid (10.1 g,51 mmol) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g,153 mmol) was dissolved in 63ml of water, and then added thereto. After this time, it was stirred well, and tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.5 mmol) was then added. After 12 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.5g of compound subDF-2 (yield 74%, MS: [ M+H ] +=412).
To 300ml of THF were added under nitrogen the compound subDF-2 (15 g,57.8 mmol) and the compound amine 35 (28.4 g,57.8 mmol), and the mixture was stirred and refluxed. Then, potassium carbonate (23.9 g,173.3 mmol) was dissolved in 72ml of water, and then added thereto. After this time, it was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was then added. After 8 hours of reaction, cooling to room temperature was performed. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. After that, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 29.4g of compound 2-30 (yield 62%, MS: [ m+h ] +=823).
Examples (example)
Comparative example A
Coated with a coating having a thickness of
The glass substrate of the ITO (indium tin oxide) film was put into distilled water in which a cleaning agent was dissolved and subjected to ultrasonic cleaning. At this time, a product manufactured by Fischer co. Was used as a detergent, and distilled water filtered twice using a filter manufactured by Millipore co. Was used as distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice using distilled water for 10 minutes. After the washing with distilled water was completed, the substrate was ultrasonically washed with isopropanol, acetone and methanol solvents, dried, and then transferred to a plasma washer. In addition, the substrate was cleaned using oxygen plasma for 5 minutes, and then transferred to a vacuum depositor.
Forming a hole injection layer on the prepared ITO transparent electrode with the following compound HI-1
And p doped at a concentration of 1.5 wt% with the following compound a-1. Then, the compound HT-1 is vacuum deposited to +.>
To form a hole transport layer. Thereafter, the following compound EB-1 was vacuum deposited to +.>
As an electron blocking layer. Then, the following compound RH-1 and compound Dp-7 were vacuum deposited to +.about.2 in a weight ratio of 98:2 on the EB-1 deposited film>
To form a red light-emitting layer. By vacuum deposition of the following compound HB-1 on the light-emitting layer to +.>
Is used to form the hole blocking layer. Then, the following compound ET-1 and the following compound LiQ are vacuum deposited on the hole blocking layer in a weight ratio of 2:1 to +.>
To form an electron injection and transport layer. Lithium fluoride (LiF) and aluminum are sequentially deposited to a thickness of +.>
And
to form a cathode. />
In the above process, the deposition rate of the organic material is maintained at
To->
The deposition rate of lithium fluoride of the cathode is kept at +.>
And maintaining the deposition rate of aluminum at +.>
In addition, the vacuum during deposition was maintained at 2X 10 -7 To 5X 10 -6 The support, thereby manufacturing the organic light emitting device.
Examples 1 to 17
An organic light-emitting device was manufactured in the same manner as in comparative example a, except that the compound shown in table 1 was used instead of the compound RH-1 as a host in the organic light-emitting device of comparative example a.
Comparative examples 1 to 7
An organic light-emitting device was manufactured in the same manner as in comparative example a, except that the compound shown in table 1 was used instead of the compound RH-1 as a host in the organic light-emitting device of comparative example a. The structures of the compounds B-8 to B-14 of Table 1 are as follows.
Examples 18 to 47
An organic light-emitting device was manufactured in the same manner as in comparative example a, except that the compound shown in table 2 was used instead of the compound EB-1 as an electron blocking layer material in the organic light-emitting device of comparative example a.
Comparative examples 8 to 14
An organic light-emitting device was manufactured in the same manner as in comparative example a, except that the compound shown in table 2 was used instead of the compound EB-1 as an electron blocking layer material in the organic light-emitting device of comparative example a. The structures of the compounds B-1 to B-7 of Table 2 are as follows.
Examples 48 to 115
An organic light-emitting device was manufactured in the same manner as in comparative example a, except that the compound of the first host and the second host described in table 3 was used in a weight ratio of 1:1 instead of the compound RH-1 as the host in the organic light-emitting device of comparative example a.
Experimental example
The driving voltage and efficiency (based on 15 mA/cm) were measured by applying a current to the organic light emitting devices prepared in the above examples 1 to 115, comparative example A and comparative examples 1 to 88 2 ) And the results are shown in tables 1 to 3. Lifetime T95 means the time taken until the initial brightness (7,000 nits) decreases to 95%.
TABLE 1
TABLE 2
TABLE 3
When current was applied to the organic light emitting devices manufactured in examples 1 to 115 and comparative examples 1 to 14, the results shown in tables 1 to 3 were obtained.
It was determined that when compounds 1-1 to 1-17 of the present disclosure were used as red hosts, the driving voltage was reduced and the efficiency and lifetime were improved as compared to the case of using the compound of the comparative example as shown in table 1. Even when compounds 2-1 to 2-30 of the present disclosure are used as the electron blocking layer, the driving voltage is reduced and the efficiency and lifetime are also improved as compared to the case of using the compound of the comparative example as shown in table 2.
Additionally, it was determined that in table 3, when one of the compounds 1-1 to 1-17 was selected as the first host and one of the compounds 2-1 to 2-30 was used as the second host, and they were used as the red host by co-deposition, the driving voltage was reduced and the efficiency and lifetime were improved as compared to the case of using a single material host.
That is, from the results of tables 1 to 3, it was determined that when the compound of one embodiment was used as a host of a red light-emitting layer or as an electron blocking layer in a red device, the driving voltage, light-emitting efficiency, and lifetime characteristics of the organic light-emitting device could be improved.
[ description of reference numerals ]
1: substrate 2: anode
3: light emitting layer 4: cathode electrode
5: hole injection layer 6: hole transport layer
7: electron blocking layer 8: hole blocking layer
9: electron injection and transport layers
Claims (13)
1. A compound represented by the following chemical formula 1:
[ chemical formula 1]
In the chemical formula 1 described above, a compound having the formula,
a is a thiazole ring or condensed with an adjacent ring
An azole ring, wherein the azole ring,
L 1 is a single bond; substituted or unsubstituted C 6-60 Arylene groups; or substituted or unsubstituted C comprising at least one selected from N, O and S 2-60 A heteroarylene group,
R 1 is that
Ar 1 To Ar 4 Each independently is a substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising at least one selected from N, O and S 2-60 A heteroaryl group, which is a group,
L 2 to L 5 Each independently is a single bond; substituted or unsubstituted C 6-60 Arylene groups; or substituted or unsubstituted C comprising at least one selected from N, O and S 2-60 A heteroarylene group,
R 2 is C substituted or unsubstituted 6-60 An aryl group; or substituted or unsubstituted C comprising at least one selected from N, O and S 2-60 A heteroaryl group, which is a group,
d is deuterium
n is an integer of 0 or more and 5 or less.
2. A compound according to claim 1,
wherein the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-4:
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
[ chemical formulas 1-4]
In chemical formulas 1-1 to 1-4,
R 1 、R 2 、L 1 d and n are as defined in claim 1.
3. A compound according to claim 1,
wherein L is 1 Is a single bond, phenylene, biphenyldiyl, or naphthalenediyl.
4. A compound according to claim 1,
wherein Ar is 1 And Ar is a group 2 Each independently is phenyl, biphenyl, naphthyl, phenanthryl, dibenzofuranyl, or dibenzothienyl.
5. A compound according to claim 1,
wherein Ar is 3 And Ar is a group 4 Each independently is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, dibenzofuranyl, dibenzothienyl, phenylcarbazolyl, or phenylnaphthyl.
6. A compound according to claim 1,
wherein L is 2 And L 3 Each independently is a single bond, phenylene, or naphthalenediyl.
7. A compound according to claim 1,
Wherein L is 4 And L 5 Each independently is a single bond, phenylene, biphenyldiyl, naphthalenediyl, or carbazolediyl.
8. A compound according to claim 1,
wherein Ar is 1 And Ar is a group 2 At least one of which is substituted or unsubstituted C 6-60 Aryl groups.
9. A compound according to claim 1,
wherein Ar is 3 And Ar is a group 4 At least one of which is substituted or unsubstituted C 6-60 Aryl groups.
10. A compound according to claim 1,
wherein R is 2 Is phenyl, biphenyl, naphthyl, dibenzofuranyl, or dibenzothienyl.
11. A compound according to claim 1,
wherein the compound represented by chemical formula 1 is any one selected from the following compounds:
12. an organic light emitting device comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more layers of organic material disposed between the first electrode and the second electrode, wherein at least one of the layers of organic material comprises at least one compound according to any one of claims 1 to 11.
13. The organic light-emitting device according to claim 12,
wherein the organic material layer is a light emitting layer or an electron blocking layer.
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