CN117480171A - 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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- CN117480171A CN117480171A CN202280039165.2A CN202280039165A CN117480171A CN 117480171 A CN117480171 A CN 117480171A CN 202280039165 A CN202280039165 A CN 202280039165A CN 117480171 A CN117480171 A CN 117480171A
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- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 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
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000012423 maintenance Methods 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-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
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 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
- WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical class C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 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
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 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
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 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
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000010992 reflux Methods 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
- 238000005507 spraying Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 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
- 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
- 150000003577 thiophenes Chemical class 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-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
- 230000007704 transition Effects 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
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 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
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- 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
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- 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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H—ELECTRICITY
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- 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
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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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
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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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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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
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K99/00—Subject matter not provided for in other groups of this subclass
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- Spectroscopy & Molecular Physics (AREA)
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- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present invention provides novel compounds and organic light emitting devices comprising the same.
Description
Technical Field
Cross reference to related applications
The present application claims priority based on korean patent application No. 10-2021-0166509, 11-29 of 2021, the entire contents of the disclosure of which are incorporated herein by reference.
The present invention relates to novel compounds and organic light emitting devices comprising the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, and excellent brightness, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.
The organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode. In order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. In such a structure of an organic light emitting device, if a voltage is applied between both electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode, and when the injected holes and electrons meet, excitons (exiton) are formed, and light is emitted when the excitons transition to the ground state again.
As for the organic matter used for the organic light emitting device as described above, development of new materials is continuously demanded.
On the other hand, in recent years, organic light emitting devices using a solution process, particularly an inkjet process, instead of the conventional vapor deposition process have been developed in order to save the process cost. In the initial stage, an attempt was made to develop an organic light-emitting device by coating all the organic light-emitting device layers by a solution process, but the conventional technology has a limitation, and therefore, in the normal configuration, only HIL, HTL, EML is studied by a solution process, and a hybrid (hybrid) process using an existing vapor deposition process is used in the subsequent process.
Accordingly, the present invention provides a novel material for an organic light emitting device which can be used for an organic light emitting device and also for a solution process.
Prior art literature
Patent literature
(patent document 0001) Korean patent laid-open No. 10-2000-0051826
Disclosure of Invention
Technical problem
The present invention relates to novel compounds and organic light emitting devices comprising the same.
Solution to the problem
The present invention provides a compound represented by the following chemical formula 1:
[ chemical formula 1]
In the above-mentioned chemical formula 1,
X 1 to X 4 One of them is CR, the others are each independently N, CH or CD,
Wherein R is a substituent represented by the following chemical formula 2,
X 5 to X 10 Each independently is N, CH or CD,
however, X is 1 To X 10 One of which is N,
[ chemical formula 2]
In the above-mentioned chemical formula 2,
L 1 is a direct bond; substituted or unsubstituted C 6-60 Arylene groups; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 A heteroarylene group,
L 2 is a direct bond; substituted or unsubstituted C 6-60 Arylene groups; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 A heteroarylene group,
L 3 is a direct bond; substituted or unsubstituted C 6-60 Arylene groups; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 A heteroarylene group,
Ar 1 is substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 A heteroaryl group, which is a group,
Ar 2 is substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 Heteroaryl groups.
In addition, the present invention provides an organic light emitting device, wherein comprising: a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, wherein the organic layer contains a compound represented by the chemical formula 1. Specifically, the organic layer containing the above compound may be a light-emitting layer.
Effects of the invention
The compound represented by the above chemical formula 1 may be used as a material of an organic layer of an organic light emitting device in which improvement of efficiency, lower driving voltage, and/or improvement of lifetime characteristics may be achieved. In particular, the compound represented by the above chemical formula 1 may be used as a material for hole injection, hole transport, hole injection and transport, electron suppression, luminescence, electron transport, or electron injection.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
Fig. 2 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron injection and transport layer 8, and a cathode 4.
Detailed Description
In the following, the invention will be described in more detail in order to aid understanding thereof.
(definition of terms)
In the present description of the invention,representation ofA bond to the other substituent, "D" represents deuterium.
In the present specification, the term "substituted or unsubstituted" means that it is selected from deuterium; a halogen group; cyano 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 group Arylthio->) The method comprises the steps of carrying out a first treatment on the surface of the Alkylsulfonyl->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; or a substituent comprising N, O and 1 or more substituents in 1 or more heteroaryl groups in the S atom is substituted or unsubstituted, or a substituent bonded to 2 or more substituents in the above-exemplified substituents is substituted or unsubstituted. For example, the "substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl or may be interpreted as a substituent in which 2 phenyl groups are linked.
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, in the ester group, 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 compound may be a compound of the following structural formula, but is not limited thereto.
In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, the silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
In the present specification, the boron group specifically includes trimethylboron group, triethylboron group, t-butyldimethylboroyl group, triphenylboron group, phenylboron group, and the like, but is not limited thereto.
In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.
In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the above alkyl group has 1 to 10 carbon atoms. According to another embodiment, the above alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, t-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, t-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 specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. 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-phenylene1-yl, 2-diphenylethylene1-yl, 2-phenyl-2- (naphthalen-1-yl) ethylene1-yl, 2-bis (diphenyl-1-yl) ethylene1-yl, stilbene, styryl and the like, but are not limited thereto.
In the present specification, cycloalkyl is not particularly limited, but is preferably cycloalkyl having 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but the present invention is not limited thereto.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, such as phenyl, biphenyl, and terphenyl, but is not limited thereto. As the polycyclic aryl groupCan be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl,A group, a fluorenyl group, etc., but is not limited thereto.
In this specification, a fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure. In the case where the above fluorenyl group is substituted, it may beEtc. However, the present invention is not limited thereto.
In the present specification, the heteroaryl group is a heteroaryl group containing 1 or more of O, N, si and S as a hetero element, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. Examples of heteroaryl groups include xanthene (xanthone), thioxanthene (thioxanthone), thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl, (-) -and (II) radicals>Diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo- >Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthroline (phenanthrinyl), iso>Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but are not limited thereto.
In the present specification, the aryl groups in the aralkyl group, the aralkenyl group, the alkylaryl group, the arylamine group, and the arylsilyl group are the same as those exemplified for the aryl groups described above. In the present specification, the alkyl group in the aralkyl group, alkylaryl group, and alkylamino group is the same as the above-mentioned alkyl group. In this specification, the heteroaryl group in the heteroaryl amine may be as described above with respect to the heteroaryl group. In the present specification, the alkenyl group in the aralkenyl group is the same as the above-described examples of alkenyl groups. In this specification, arylene is a 2-valent group, and the above description of aryl can be applied in addition to this. In this specification, the heteroarylene group is a 2-valent group, and the above description of the heteroaryl group can be applied thereto. In this specification, the hydrocarbon ring is not a 1-valent group, but a combination of 2 substituents, and the above description of the aryl group or cycloalkyl group can be applied. In this specification, a heterocyclic ring is not a 1-valent group but a combination of 2 substituents, and the above description of heteroaryl groups can be applied thereto.
(Compound)
The present invention provides a compound represented by the above chemical formula 1.
X 1 To X 4 One of them is CR and the others are N, CH or CD, respectively, wherein R is a substituent represented by the following chemical formula 2, X 5 To X 10 Each independently is N, CH or CD, but X 1 To X 10 One of which is N.
Specifically, it may be X 1 To X 4 One of them is CR, the other is N, the others are each independently CH or CD, X 5 To X 10 Each independently is CH or CD, or X 1 To X 4 One of them is CR and the others are each independently CH or CD, X 5 To X 10 One of them is N and the others are each independently CH or CD.
L 1 Is a direct bond; substituted or unsubstituted C 6-60 Arylene groups; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 Heteroarylene group. Preferably L 1 May be a direct bond or phenylene. L (L) 1 In the case of phenylene, may not be takenSubstituted with more than 1 deuterium.
L 2 Is a direct bond; substituted or unsubstituted C 6-60 Arylene groups; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 Heteroarylene group. Preferably L 2 Can be a direct bond, phenylene, naphthylene, biphenylene, 9-dimethyl-fluorenylene, or 9, 9-diphenyl-fluorenylene. L (L) 2 In the case of phenylene, naphthylene, biphenylene, 9-dimethyl-fluorenylene, or 9, 9-diphenyl-fluorenylene, they may be unsubstituted or substituted with more than 1 deuterium.
L 3 Is a direct bond; substituted or unsubstituted C 6-60 Arylene groups; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 Heteroarylene group. Preferably L 3 Can be a direct bond, phenylene, naphthylene, biphenylene, 9-dimethyl-fluorenylene, or 9, 9-diphenyl-fluorenylene. L (L) 3 In the case of phenylene, naphthylene, biphenylene, 9-dimethyl-fluorenylene, or 9, 9-diphenyl-fluorenylene, they may be unsubstituted or substituted with more than 1 deuterium.
Ar 1 Is substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 Heteroaryl groups. Ar (Ar) 1 Can be phenyl, biphenyl, terphenyl, naphthyl, 9-dimethyl-fluorenyl, 9-diphenyl-fluorenyl, dibenzofuranyl, dibenzothienyl, 9-phenyl-carbazolyl, or 9,9' -spirodi [ 9H-fluorenyl ]]A base. Ar (Ar) 1 May be unsubstituted or substituted with more than 1 deuterium.
Ar 2 Is substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 Heteroaryl groups. Ar (Ar) 2 Can be phenyl, biphenyl, terphenyl, naphthyl, 9-dimethyl-fluorenyl, 9-diphenyl-fluorenyl, dibenzofuranyl, dibenzothienyl, 9-phenyl-carbazolyl, or 9,9' -spirodi [ 9H-fluorenyl ]]A base. Ar (Ar) 2 May be unsubstituted or substituted with more than 1 deuterium.
In addition, the compound may be a compound represented by any one of the following chemical formulas 1-1 to 1-4.
[ chemical formula 1-1]
In the above-mentioned chemical formula 1-1,
X 2 to X 10 One of which is N, the remainder each independently being CH or CD,
L 1 to L 3 、Ar 1 And Ar is a group 2 As defined in the chemical formula 1,
[ chemical formulas 1-2]
In the above-mentioned chemical formula 1-2,
X 1 and X 3 To X 10 One of which is N, the remainder each independently being CH or CD,
L 1 to L 3 、Ar 1 And Ar is a group 2 As defined in the chemical formula 1,
[ chemical formulas 1-3]
In the above-mentioned chemical formulas 1 to 3,
X 1 、X 2 and X 4 To X 10 One of which is N, the remainder each independently being CH or CD,
L 1 to L 3 、Ar 1 And Ar is a group 2 As defined in the chemical formula 1,
[ chemical formulas 1-4]
In the above-mentioned chemical formulas 1 to 4,
X 1 to X 3 And X 5 To X 10 One of which is N, the remainder each independently being CH or CD,
L 1 to L 3 、Ar 1 And Ar is a group 2 The same definition as in chemical formula 1.
Representative examples of the compounds represented by the above chemical formula 1 are shown below:
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The compound may contain no deuterium, or may contain 1 or more deuterium.
On the other hand, as an example, the present invention provides a method for producing a compound represented by the above chemical formula 1 as shown in the following reaction formulas 1 and 2:
[ reaction type 1]
[ reaction type 2]
In the above equations 1 and 2, X 1 To X 10 、L 1 To L 3 And Ar 1 And Ar is a group 2 Is defined as in chemical formulas 1 and 2, respectively. In addition, in equations 1 and 2, Z is halogen, preferably chlorine.
The above reaction formula 1 is a reaction for producing chemical formula 1 as a core structure by suzuki coupling reaction. In addition, equation 2 is also a suzuki coupling reaction, preferably in the presence of a palladium catalyst, and the reactive groups for the suzuki coupling reaction may be varied according to techniques known in the art. The above-described production method can be more specifically described in the production examples and the synthesis examples described later.
(organic light-emitting device)
In addition, the present invention provides an organic light emitting device including the compound represented by the above chemical formula 1. As one example, the present invention provides an organic light emitting device, including: a first electrode, a second electrode provided opposite to the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains a compound represented by the chemical formula 1.
The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure or a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like as an organic layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers.
The organic layer may include a hole injection layer, a hole transport layer, or a layer that performs hole injection and transport simultaneously, and the hole injection layer, the hole transport layer, or the layer that performs hole injection and transport simultaneously may include a compound represented by chemical formula 1.
The organic layer may include a light-emitting layer, and the light-emitting layer may include a compound represented by chemical formula 1.
The organic layer may include a hole blocking layer, an electron transporting layer, an electron injecting layer, or a layer that performs both electron transport and electron injection, and the hole blocking layer, the electron transporting layer, the electron injecting layer, or the layer that performs both electron transport and electron injection may include a compound represented by chemical formula 1.
In addition, the organic layer may include a light emitting layer, and an electron injection and transport layer, and the electron injection and transport layer may include a compound represented by the chemical formula 1.
In addition, the organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate. Further, the organic light emitting device according to the present invention may be an organic light emitting device of a reverse structure (inverted type) in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate. For example, a structure of an organic light emitting device according to an embodiment of the present invention is illustrated in fig. 1 and 2.
Fig. 1 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
Fig. 2 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron injection and transport layer 8, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above light emitting layer.
The organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that 1 or more of the above organic layers include the compound represented by chemical formula 1. In addition, when the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking an anode, an organic layer, and a cathode on a substrate. This can be manufactured as follows: PVD (physical Vapor Deposition) process such as sputtering (sputtering) or electron beam evaporation (physical vapor deposition) is used to vapor-deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode, then an organic 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 substance that can be used as a cathode is vapor-deposited on the organic layer. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
In addition, the compound represented by the above chemical formula 1 may be used not only in a vacuum deposition method but also in a solution coating method to form an organic layer in the production of an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.
As an example, the first electrode may be an anode, the second electrode may be a cathode, or the first electrode may be a cathode, and the second electrode may be an anode.
As the anode material, a material having a large work function is generally preferable in order to allow holes to be smoothly injected into the organic layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); znO of Al or SnO 2 A combination of metals such as Sb and the like and oxides; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive compounds such as (PEDOT), polypyrrole and polyaniline, etc., but are not limited thereto.
As the cathode material, a material having a small work function is generally preferred in order to facilitate injection of electrons into the organic 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, and alloys thereof; liF/Al or LiO 2 And/or Al, but is not limited thereto.
The hole injection layer is a layer that injects holes from an electrode, and the following compounds are preferable as the hole injection substance: a compound which has a hole transporting ability, has an effect of injecting holes from the anode, has an excellent hole injecting effect for the light emitting layer or the light emitting material, prevents excitons generated in the light emitting layer from migrating to the electron injecting layer or the electron injecting material, and has an excellent thin film forming ability. The HOMO (highest occupied molecular orbital ) of the hole-injecting substance is preferably between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophenes, arylamine-based organic substances, hexanitrile hexaazabenzophenanthrene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive compounds.
The hole-transporting layer is a layer that receives holes from the hole-injecting layer and transports the holes to the light-emitting layer, and a hole-transporting substance that can receive holes from the anode or the hole-injecting layer and transfer the holes to the light-emitting layer is preferable, and a substance having a large mobility to the holes is preferable. Specific examples include, but are not limited to, arylamine-based organic substances, conductive compounds, and block copolymers in which conjugated moieties and non-conjugated moieties are present at the same time.
The light-emitting substance is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and is preferably a substance having high quantum efficiency for fluorescence or phosphorescence. Specifically, there are 8-hydroxyquinoline aluminum complex (Alq 3 ) The method comprises the steps of carrying out a first treatment on the surface of the Carbazole-based compounds; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (E) benzo (EAzole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
The electron suppression layer is a layer interposed between the hole transport layer and the light emitting layer, and is also called an electron blocking layer, in order to prevent electrons injected from the cathode from being transferred to the hole transport layer without recombination in the light emitting layer. The electron-inhibiting layer preferably uses a substance having a smaller electrophilic capacity than the electron-transporting layer. Preferably, a compound represented by the above chemical formula 1 may be contained as the substance of the electron suppression layer.
The light emitting layer may include a host material and a dopant material. As the host material, a compound represented by the above chemical formula 1 can be used. Further, as a host material which can be used further, an aromatic condensed ring derivative, a heterocyclic compound or the like can be used. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds Pyrimidine derivatives, etc., but are not limited thereto.
Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is an aromatic condensed ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene having an arylamino group,Bisindenopyrene, and the like, and a styrylamine compound is a compound in which at least 1 arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with 1 or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specifically, there are styrylamine, styrylenediamine, styrylenetriamine, styrylenetetramine, and the like, but the present invention is not limited thereto. The metal complex includes, but is not limited to, iridium complex, platinum complex, and the like. />
The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer, and the electron transport material is a material that can well receive electrons from the cathode and transfer the electrons to the light emitting layer, and has a high mobility to electronsSubstances are suitable. Specifically, there is an Al complex of 8-hydroxyquinoline containing Alq 3 But not limited to, complexes of (c) and (d), organic radical compounds, hydroxyflavone-metal complexes, and the like. The electron transport layer may be used with any desired cathode material as used in the art. In particular, examples of suitable cathode materials are the usual materials having a low work function accompanied by an aluminum layer or a silver layer. In particular cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum layer or a silver layer.
The electron injection layer is a layer that injects electrons from an electrode, and preferably the following compound is used: a compound which has an ability to transport electrons, an effect of injecting electrons from a cathode, an excellent electron injection effect for a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole injection layer, and has excellent thin film forming ability. Specifically, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,Azole,/->Examples of the compound include, but are not limited to, diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives.
Examples of the metal complex 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 (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
In the present invention, the "electron injection and transport layer" is a layer that fully exerts the functions of the electron injection layer and the electron transport layer, and the functions of the layers may be used singly or in combination. Preferably, a compound represented by the above chemical formula 1 may be included as a substance of the electron injection and transport layer.
The organic light emitting device according to the present invention may be a Bottom emission (Bottom emission) device, a Top emission (Top emission) device, or a bi-directional light emitting device, and in particular, may be a Bottom emission device requiring relatively high light emitting efficiency.
In addition, the compound according to the present invention may be contained in an organic solar cell or an organic transistor in addition to the organic light emitting device.
The production of the compound represented by the above chemical formula 1 and the organic light emitting device including the same is specifically illustrated in the following examples. However, the following examples are given by way of illustration of the present invention, and the scope of the present invention is not limited thereto.
Synthesis example A-1-1: production of intermediate compound A-1-1
3-bromo-2-chloropyridine (15 g,77.9 mmol) and (3- (methylthio) naphthalen-2-yl) boronic acid (17.8 g,81.8 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (32.3 g,233.8 mmol) was dissolved in 100ml of water and the mixture was poured, and after stirring the mixture sufficiently, bis (tri-t-butylphosphine) palladium (0) (0.4 g,0.8 mmol) was poured. After 4 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 13.8g of compound A-1-1_P1 was produced. (yield 62%, MS: [ M+H) ] + ＝286)
Compound A-1-1_P1 (15 g,52.5 mmol) and hydrogen peroxide (2.7 g,78.7 mmol) were added to 300ml of acetic acid, stirred and refluxed. After 3 hours of reaction, cool to normal temperature and pour the reactants into 6The crystals were dropped into 00ml of water and filtered. The filtered solid was dissolved in chloroform, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, filtration was performed, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 8.1g of compound A-1-1_P2 was produced. (yield 51%, MS: [ M+H ]] + ＝302)
Compound A-1-1_P2 (15 g,49.7 mmol) was added to 300ml of sulfuric acid, stirred and refluxed. After 2 hours of reaction, the reaction mixture was cooled to room temperature, poured into 600ml of water, and the crystals were allowed to fall down and filtered. The filtered solid was dissolved in chloroform, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, filtration was performed, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 6.2g of compound A-1-1 was produced. (yield 49%, MS: [ M+H)] + ＝254)
Synthesis examples A-1 to 6: production of intermediate Compounds A-1-6
1-bromo-2-chlorobenzene (15 g,78.3 mmol) and (7- (methylthio) isoquinolin-6-yl) boronic acid (18 g,82.3 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (32.5 g,235 mmol) was dissolved in 100ml of water and added thereto, and after stirring well, bis (tri-t-butylphosphine) palladium (0) (0.4 g,0.8 mmol) was added thereto. After 4 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 15.4g of compound A-1-6_P1 was produced. (yield 69%, MS: [ M+H) ] + ＝286)
Compound A-1-6_P1 (15 g,52.5 mmol) and hydrogen peroxide (2.7 g,78.7 mmol) were added to 300ml of acetic acid, stirred and refluxed. After 3 hours of reaction, the reaction mixture was cooled to room temperature, poured into 600ml of water, and the crystals were allowed to fall down and filtered. Solids to be filteredAfter dissolving in chloroform and washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, the filtrate was filtered and distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 8.2g of compound A-1-6_P2 was produced. (yield 52%, MS: [ M+H)] + ＝302)
Compound A-1-6_P2 (15 g,49.7 mmol) was added to 300ml of sulfuric acid, stirred and refluxed. After 5 hours of reaction, the reaction mixture was cooled to room temperature, poured into 600ml of water, and the crystals were allowed to fall down and filtered. The filtered solid was dissolved in chloroform, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, filtration was performed, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 5.9g of compound A-1-6 was produced. (yield 47%, MS: [ M+H)] + ＝254)
Synthesis example A-2-2: production of intermediate compound A-2-2
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4-bromo-2-chloropyridine (15 g,77.9 mmol) and (3- (methylthio) naphthalen-2-yl) boronic acid (17.8 g,81.8 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (32.3 g,233.8 mmol) was dissolved in 100ml of water and the mixture was poured, and after stirring the mixture sufficiently, bis (tri-t-butylphosphine) palladium (0) (0.4 g,0.8 mmol) was poured. After 2 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 13.8g of compound A-2-2_P1 was produced. (yield 62%, MS: [ M+H) ] + ＝286)
Compound A-2-2_P1 (15 g,52.5 mmol) and hydrogen peroxide (2.7 g,78.7 mmol) were added to 300ml of acetic acid, stirred and refluxed. After 4 hours of reaction, the reaction mixture was cooled to room temperature, poured into 600ml of water, and the crystals were allowed to fall down and filtered. Dissolving the filtered solid in chloroform, washing with water for 2 times, separating organic layer, adding the mixture withoutShui Liusuan magnesium, stirring, filtering, and distilling the filtrate under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 8.7g of compound A-2-2_P2 was produced. (yield 55%, MS: [ M+H)] + ＝302)
Compound A-2-2_P2 (15 g,49.7 mmol) was added to 300ml of sulfuric acid, stirred and refluxed. After 2 hours of reaction, the reaction mixture was cooled to room temperature, poured into 600ml of water, and the crystals were allowed to fall down and filtered. The filtered solid was dissolved in chloroform, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, filtration was performed, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 6.8g of compound A-2-2 was produced. (yield 54%, MS: [ M+H)] + ＝254)
Synthesis example A-2-4: production of intermediate compound A-2-4
1-bromo-3-chlorobenzene (15 g,78.3 mmol) and (2- (methylthio) quinolin-3-yl) boronic acid (18 g,82.3 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (32.5 g,235 mmol) was dissolved in 100ml of water and added thereto, and after stirring well, bis (tri-t-butylphosphine) palladium (0) (0.4 g,0.8 mmol) was added thereto. After 4 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 13.8g of compound A-2-4_P1 was produced. (yield 62%, MS: [ M+H) ] + ＝286)
Compound A-2-4_P1 (15 g,52.5 mmol) and hydrogen peroxide (2.7 g,78.7 mmol) were added to 300ml of acetic acid, stirred and refluxed. After 5 hours of reaction, the reaction mixture was cooled to room temperature, poured into 600ml of water, and the crystals were allowed to fall down and filtered. The filtered solid was dissolved in chloroform, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, filtration was performed, and the filtrate was distilled under reduced pressure. Will be concentratedThe compound was purified by silica gel column chromatography, whereby 9.3g of compound A-2-4_P2 was produced. (yield 59%, MS: [ M+H)] + ＝302)
Compound A-2-4_P2 (15 g,49.7 mmol) was added to 300ml of sulfuric acid, stirred and refluxed. After 2 hours of reaction, the reaction mixture was cooled to room temperature, poured into 600ml of water, and the crystals were allowed to fall down and filtered. The filtered solid was dissolved in chloroform, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, filtration was performed, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 7.2g of compound A-2-4 was produced. (yield 57%, MS: [ M+H)] + ＝254)
Synthesis examples A-2 to 7: production of intermediate compound A-2-7
1-bromo-3-chlorobenzene (15 g,78.3 mmol) and (6- (methylthio) isoquinolin-7-yl) boronic acid (18 g,82.3 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (32.5 g,235 mmol) was dissolved in 100ml of water and added thereto, and after stirring well, bis (tri-t-butylphosphine) palladium (0) (0.4 g,0.8 mmol) was added thereto. After 3 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 14.3g of compound A-2-7_P1 was produced. (yield 64%, MS: [ M+H) ] + ＝286)
Compound A-2-7_P1 (15 g,52.5 mmol) and hydrogen peroxide (2.7 g,78.7 mmol) were added to 300ml of acetic acid, stirred and refluxed. After 5 hours of reaction, the reaction mixture was cooled to room temperature, poured into 600ml of water, and the crystals were allowed to fall down and filtered. The filtered solid was dissolved in chloroform, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, filtration was performed, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to thereby prepare 9.2g of a compoundCompound A-2-7_P2. (yield 58%, MS: [ M+H)] + ＝302)
Compound A-2-7_P2 (15 g,49.7 mmol) was added to 300ml of sulfuric acid, stirred and refluxed. After 4 hours of reaction, the reaction mixture was cooled to room temperature, poured into 600ml of water, and the crystals were allowed to fall down and filtered. The filtered solid was dissolved in chloroform, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, filtration was performed, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 5.4g of compound A-2-7 was produced. (yield 43%, MS: [ M+H)] + ＝254)
Synthesis example A-3-5: production of intermediate compound A-3-5
1-bromo-4-chlorobenzene (15 g,78.3 mmol) and (7- (methylthio) quinolin-6-yl) boronic acid (18 g,82.3 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (32.5 g,235 mmol) was dissolved in 100ml of water and added thereto, and after stirring well, bis (tri-t-butylphosphine) palladium (0) (0.4 g,0.8 mmol) was added thereto. After 4 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 15.4g of compound A-3-5_P1 was produced. (yield 69%, MS: [ M+H) ] + ＝286)
Compound A-3-5_P1 (15 g,52.5 mmol) and hydrogen peroxide (2.7 g,78.7 mmol) were added to 300ml of acetic acid, stirred and refluxed. After 4 hours of reaction, the reaction mixture was cooled to room temperature, poured into 600ml of water, and the crystals were allowed to fall down and filtered. The filtered solid was dissolved in chloroform, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, filtration was performed, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 9g of compound A-3-5_P2 was produced. (yield 57%, MS: [ M+H)] + ＝302)
Compound A-3-5_P2 (15 g,49.7 mmol) was added to 300ml of sulfuric acid, stirred and refluxed. After 2 hours of reaction, the reaction mixture was cooled to room temperature, poured into 600ml of water, and the crystals were allowed to fall down and filtered. The filtered solid was dissolved in chloroform, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, filtration was performed, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 5.9g of compound A-3-5 was produced. (yield 47%, MS: [ M+H)] + ＝254)
Synthesis examples A-3 to 9: production of intermediate compound A-3-9
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1-bromo-4-chlorobenzene (15 g,78.3 mmol) and (3- (methylthio) quinolin-2-yl) boronic acid (18 g,82.3 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (32.5 g,235 mmol) was dissolved in 100ml of water and added thereto, and after stirring well, bis (tri-t-butylphosphine) palladium (0) (0.4 g,0.8 mmol) was added thereto. After 5 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 13.4g of compound A-3-9_P1 was produced. (yield 60%, MS: [ M+H) ] + ＝286)
Compound A-3-9_P1 (15 g,52.5 mmol) and hydrogen peroxide (2.7 g,78.7 mmol) were added to 300ml of acetic acid, stirred and refluxed. After 3 hours of reaction, the reaction mixture was cooled to room temperature, poured into 600ml of water, and the crystals were allowed to fall down and filtered. The filtered solid was dissolved in chloroform, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, filtration was performed, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 8.1g of compound A-3-9_P2 was produced. (yield 51%, MS: [ M+H ]] + ＝302)
Compound A-3-9_P2 (15 g,49.7 mmol) was added toIn 300ml of sulfuric acid, stirring and refluxing. After 5 hours of reaction, the reaction mixture was cooled to room temperature, poured into 600ml of water, and the crystals were allowed to fall down and filtered. The filtered solid was dissolved in chloroform, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, filtration was performed, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 5g of compound A-3-9 was produced. (yield 40%, MS: [ M+H)] + ＝254)
Synthesis example A-4-3: production of intermediate compound A-4-3
4-bromo-2-chloropyridine (15 g,77.9 mmol) and (3- (methylthio) naphthalen-2-yl) boronic acid (17.8 g,81.8 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (32.3 g,233.8 mmol) was dissolved in 100ml of water and the mixture was poured, and after stirring the mixture sufficiently, bis (tri-t-butylphosphine) palladium (0) (0.4 g,0.8 mmol) was poured. After 3 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 15.6g of compound A-4-3_P1 was produced. (yield 70%, MS: [ M+H) ] + ＝286)
Compound A-4-3_P1 (15 g,52.5 mmol) and hydrogen peroxide (2.7 g,78.7 mmol) were added to 300ml of acetic acid, stirred and refluxed. After 4 hours of reaction, the reaction mixture was cooled to room temperature, poured into 600ml of water, and the crystals were allowed to fall down and filtered. The filtered solid was dissolved in chloroform, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, filtration was performed, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 9g of compound A-4-3_P2 was produced. (yield 57%, MS: [ M+H)] + ＝302)
Compound A-4-3_P2 (15 g,49.7 mmol) was added to 300ml of sulfuric acid, stirred and refluxed. After 5 hours of reaction, cool to normalThe reaction was poured into 600ml of water at a temperature to drop the crystals, and filtration was performed. The filtered solid was dissolved in chloroform, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, filtration was performed, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 5.7g of compound A-4-3 was produced. (yield 45%, MS: [ M+H ]] + ＝254)
Synthesis example A-4-8: production of intermediate compound A-4-8
1-bromo-3-chlorobenzene (15 g,78.3 mmol) and (6- (methylthio) isoquinolin-7-yl) boronic acid (18 g,82.3 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (32.5 g,235 mmol) was dissolved in 100ml of water and added thereto, and after stirring well, bis (tri-t-butylphosphine) palladium (0) (0.4 g,0.8 mmol) was added thereto. After 2 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 13.8g of compound A-4-8_P1 was produced. (yield 62%, MS: [ M+H) ] + ＝286)
Compound A-4-8_P1 (15 g,52.5 mmol) and hydrogen peroxide (2.7 g,78.7 mmol) were added to 300ml of acetic acid, stirred and refluxed. After 5 hours of reaction, the reaction mixture was cooled to room temperature, poured into 600ml of water, and the crystals were allowed to fall down and filtered. The filtered solid was dissolved in chloroform, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, filtration was performed, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 8.2g of compound A-4-8_P2 was produced. (yield 52%, MS: [ M+H)] + ＝302)
Compound A-4-8_2 (15 g,49.7 mmol) was added to 300ml of sulfuric acid, stirred and refluxed. After 5 hours of reaction, the mixture was cooled to room temperature, and the crystals were dropped by pouring the reaction mixture into 600ml of waterAnd (5) filtering. The filtered solid was dissolved in chloroform, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, filtration was performed, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 7g of compound A-4-8 was produced. (yield 56%, MS: [ M+H)] + ＝254)
Synthesis example 1: production of Compound 1
First, in Synthesis example A-2-2, an intermediate compound A-2-3 was produced in the same manner as in Synthesis example A-2-2, except that 3-bromo-5-chloropyridine was used as a starting material instead of 4-bromo-2-chloropyridine.
Then, intermediate compound A-2-3 (15 g,55.6 mmol), amine (amine) 1 (18.7 g,55.6 mmol), sodium t-butoxide (8 g,83.4 mmol) were added to 300ml of xylene under nitrogen atmosphere, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 21.8g of compound 1 was obtained. (yield 69%, MS: [ M+H)] + ＝569)
Synthesis example 2: production of Compound 2
Intermediate compound A-2-2 (15 g,55.6 mmol), amine 2 (19.5 g,55.6 mmol), sodium tert-butoxide (8 g,83.4 mmol) were added to 300ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved again in chloroform, and washed with water 2 timesThe organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 19.5g of compound 2 was obtained. (yield 60%, MS: [ M+H) ] + ＝585)
Synthesis example 3: production of Compound 3
First, in Synthesis example A-4-3, an intermediate compound A-4-2 was produced in the same manner as in Synthesis example A-4-3, except that 3-bromo-5-chloropyridine was used as a starting material instead of 4-bromo-2-chloropyridine.
Then, intermediate compound A-4-2 (15 g,55.6 mmol), amine 3 (18.7 g,55.6 mmol), sodium t-butoxide (8 g,83.4 mmol) were added to 300ml of xylene under nitrogen atmosphere, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 1958.8g of compound 3 was obtained. (yield 62%, MS: [ M+H)] + ＝56817)
Synthesis example 4: production of Compound 4
First, in Synthesis example A-4-3, an intermediate compound A-3-2 was produced in the same manner as in Synthesis example A-4-3, except that 2-bromo-5-chloropyridine was used as a starting material instead of 4-bromo-2-chloropyridine.
Then, intermediate compound A-3-2 (15 g,55.6 mmol), amine 4 (19.4 g,55.6 mmol), sodium t-butoxide (8 g,83.4 mmol) were added to 300ml of xylene under nitrogen atmosphere, stirred and refluxed. Then, bis (tri-t-butyl) is added Phosphine) palladium (0) (0.3 g,0.6 mmol). After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 21.4g of compound 4 was obtained. (yield 66%, MS: [ M+H)] + ＝583)
Synthesis example 5: production of Compound 5
First, in Synthesis example A-2-2, an intermediate compound A-3-3 was produced in the same manner as in Synthesis example A-2-2, except that 5-bromo-2-chloropyridine was used as a starting material instead of 4-bromo-2-chloropyridine.
Then, intermediate compound A-3-3 (15 g,55.6 mmol), amine 5 (18.7 g,55.6 mmol), sodium t-butoxide (8 g,83.4 mmol) were added to 300ml of xylene under nitrogen atmosphere, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 20.9g of compound 5 was obtained. (yield 66%, MS: [ M+H) ] + ＝569)
Synthesis example 6: production of Compound 6
First, in Synthesis example A-4-3, an intermediate compound A-3-7 was produced in the same manner as in Synthesis example A-4-3, except that 5-bromo-2-chloropyridine was used as a starting material instead of 4-bromo-2-chloropyridine.
Then, the intermediate is combined under nitrogen atmosphereTo 300ml of xylene were added the mixture of A-3-7 (15 g,55.6 mmol), amine 6 (22.8 g,55.6 mmol) and sodium tert-butoxide (8 g,83.4 mmol), stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 25.8g of compound 6 was obtained. (yield 72%, MS: [ M+H)] + ＝644)
Synthesis example 7: production of Compound 7
First, in Synthesis example A-4-3, an intermediate compound A-2-1 was produced in the same manner as in Synthesis example A-4-3, except that 2-bromo-6-chloropyridine was used as a starting material instead of 4-bromo-2-chloropyridine.
Then, intermediate compound A-2-1 (15 g,55.6 mmol), amine 7 (18.7 g,55.6 mmol), sodium t-butoxide (8 g,83.4 mmol) were added to 300ml of xylene under nitrogen atmosphere, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 23.1g of compound 7 was obtained. (yield 73%, MS: [ M+H) ] + ＝569)
Synthesis example 8: production of Compound 8
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First, in Synthesis example A-1-1, an intermediate compound A-1-3 was produced in the same manner as in Synthesis example A-1-1, except that 3-bromo-4-chloropyridine was used as a starting material instead of 3-bromo-2-chloropyridine.
Then, intermediate compound A-1-3 (15 g,55.6 mmol), amine 8 (17.9 g,55.6 mmol), sodium t-butoxide (8 g,83.4 mmol) were added to 300ml of xylene under nitrogen atmosphere, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 21g of compound 8 was obtained. (yield 68%, MS: [ M+H)] + ＝555)
Synthesis example 9: production of Compound 9
Intermediate compound A-2-2 (15 g,55.6 mmol), amine 9 (13.6 g,55.6 mmol), sodium tert-butoxide (8 g,83.4 mmol) were added to 300ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 19.9g of compound 9 was obtained. (yield 75%, MS: [ M+H) ] + ＝479)
Synthesis example 10: production of Compound 10
First, in Synthesis example A-4-3, an intermediate compound A-3-7 was produced in the same manner as in Synthesis example A-4-3, except that 5-bromo-2-chloropyridine was used as a starting material instead of 4-bromo-2-chloropyridine.
Then, intermediate compound A-3-7 (15 g,55.6 mmol), amine 10 (22.1 g,55.6 mmol), sodium t-butoxide (8 g,83.4 mmol) were added to 300ml of xylene under nitrogen atmosphere, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 25.9g of compound 10 was obtained. (yield 74%, MS: [ M+H ]] + ＝631)
Synthesis example 11: production of Compound 11
First, in Synthesis example A-4-3, an intermediate compound A-2-1 was produced in the same manner as in Synthesis example A-4-3, except that 2-bromo-6-chloropyridine was used as a starting material instead of 4-bromo-2-chloropyridine.
Then, intermediate compound A-2-1 (15 g,55.6 mmol), amine 11 (17.9 g,55.6 mmol), sodium t-butoxide (8 g,83.4 mmol) were added to 300ml of xylene under nitrogen atmosphere, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 19.7g of compound 11 was obtained. (yield 64%, MS: [ M+H) ] + ＝555)
Synthesis example 12: production of Compound 12
Under nitrogen atmosphereIntermediate compound A-3-9 (15 g,55.6 mmol), amine 12 (26.9 g,55.6 mmol), sodium t-butoxide (8 g,83.4 mmol) were added to 300ml of xylene, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 29.9g of compound 12 was obtained. (yield 75%, MS: [ M+H)] + ＝717)
Synthesis example 13: production of Compound 13
First, in Synthesis example A-2-7, an intermediate compound A-2-8 was produced in the same manner as in Synthesis example A-2-7, except that (6- (methylthio) quinolin-7-yl) boric acid was used as a starting material instead of (6- (methylthio) isoquinolin-7-yl) boric acid.
Then, compound A-2-8 (15 g,55.6 mmol), amine 13 (26.9 g,55.6 mmol), sodium t-butoxide (8 g,83.4 mmol) were added to 300ml of xylene under nitrogen atmosphere, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 28.7g of compound 13 was obtained. (yield 72%, MS: [ M+H) ] + ＝717)
Synthesis example 14: production of Compound 14
Under nitrogen atmosphere, compound A-2-7 (15 g,55.6 mmol),Amine 14 (17.9 g,55.6 mmol) and sodium tert-butoxide (8 g,83.4 mmol) were added to 300ml of xylene, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 21g of compound 14 was obtained. (yield 68%, MS: [ M+H)] + ＝555)
Synthesis example 15: production of Compound 15
First, in Synthesis example A-3-5, an intermediate compound A-3-6 was produced in the same manner as in Synthesis example A-3-5 except that (7- (methylthio) isoquinolin-6-yl) boric acid was used as a starting material instead of (7- (methylthio) quinolin-6-yl) boric acid.
Then, intermediate compound A-3-6 (15 g,55.6 mmol), amine 15 (22.1 g,55.6 mmol), sodium t-butoxide (8 g,83.4 mmol) were added to 300ml of xylene under nitrogen atmosphere, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 22.8g of compound 15 was obtained. (yield 65%, MS: [ M+H ] ] + ＝631)
Synthesis example 16: production of Compound 16
Compound A-3-5 (15 g,55.6 mmol), amine 16 (20.7 g,55.6 mmol), sodium tert-butoxide (8 g)83.4 mmol) was added to 300ml of xylene, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 22.2g of compound 16 was obtained. (yield 66%, MS: [ M+H)] + ＝605)
Synthesis example 17: production of Compound 17
First, in Synthesis example A-3-5, an intermediate compound A-3-4 was produced in the same manner as in Synthesis example A-3-5, except that (2- (methylthio) quinolin-3-yl) boric acid was used as a starting material instead of (7- (methylthio) quinolin-6-yl) boric acid.
Then, intermediate compound A-3-4 (15 g,55.6 mmol), amine 17 (20.1 g,55.6 mmol), sodium t-butoxide (8 g,83.4 mmol) were added to 300ml of xylene under nitrogen atmosphere, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 24.8g of compound 17 was obtained. (yield 75%, MS: [ M+H) ] + ＝595)
Synthesis example 18: production of Compound 18
First, in Synthesis example A-1-1, an intermediate compound A-1-3 was produced in the same manner as in Synthesis example A-1-1, except that 3-bromo-4-chloropyridine was used as a starting material instead of 3-bromo-2-chloropyridine.
Then, intermediate compound A-1-3 (15 g,55.6 mmol), amine 18 (19.4 g,55.6 mmol), sodium t-butoxide (8 g,83.4 mmol) were added to 300ml of xylene under nitrogen atmosphere, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 19.7g of compound 18 was obtained. (yield 61%, MS: [ M+H)] + ＝583)
Synthesis example 19: production of Compound 19
First, in Synthesis example A-4-3, an intermediate compound A-3-7 was produced in the same manner as in Synthesis example A-4-3, except that 5-bromo-2-chloropyridine was used as a starting material instead of 4-bromo-2-chloropyridine.
Then, intermediate compound A-3-7 (15 g,55.6 mmol), amine 19 (20.3 g,55.6 mmol), sodium t-butoxide (8 g,83.4 mmol) were added to 300ml of xylene under nitrogen atmosphere, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 20.6g of compound 19 was obtained. (yield 62%, MS: [ M+H) ] + ＝599)
Synthesis example 20: production of Compound 20
First, in Synthesis example A-4-3, an intermediate compound A-3-1 was produced in the same manner as in Synthesis example A-4-3, except that 2-bromo-5-chloropyridine was used as a starting material instead of 4-bromo-2-chloropyridine.
Then, intermediate compound A-3-1 (15 g,55.6 mmol), amine 20 (21.2 g,55.6 mmol), sodium t-butoxide (8 g,83.4 mmol) were added to 300ml of xylene under nitrogen atmosphere, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 23.6g of compound 20 was obtained. (yield 69%, MS: [ M+H)] + ＝615)
Synthesis example 21: production of Compound 21
Intermediate compound A-2-2 (15 g,55.6 mmol), amine 21 (27 g,55.6 mmol), sodium tert-butoxide (8 g,83.4 mmol) were added to 300ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 28.4g of compound 21 was obtained. (yield 71%, MS: [ M+H) ] + ＝719)
Synthesis example 22: production of Compound 22
First, in Synthesis example A-4-3, an intermediate compound A-3-1 was produced in the same manner as in Synthesis example A-4-3, except that 2-bromo-5-chloropyridine was used as a starting material instead of 4-bromo-2-chloropyridine.
Then, intermediate compound A-3-1 (15 g,55.6 mmol), amine 22 (20.1 g,55.6 mmol), sodium t-butoxide (8 g,83.4 mmol) were added to 300ml of xylene under nitrogen atmosphere, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 21.1g of compound 22 was obtained. (yield 64%, MS: [ M+H)] + ＝595)
Synthesis example 23: production of Compound 23
First, in Synthesis example A-2-2, an intermediate compound A-3-3 was produced in the same manner as in Synthesis example A-2-2, except that 5-bromo-2-chloropyridine was used as a starting material instead of 4-bromo-2-chloropyridine.
Then, intermediate compound A-3-3 (15 g,55.6 mmol), amine 23 (22.1 g,55.6 mmol), sodium t-butoxide (8 g,83.4 mmol) were added to 300ml of xylene under nitrogen atmosphere, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 21g of compound 23 was obtained. (yield 60%, MS: [ M+H) ] + ＝631)
Synthesis example 24: production of Compound 24
Intermediate compound A-4-3 (15 g,55.6 mmol), amine 24 (26.9 g,55.6 mmol), sodium tert-butoxide (8 g,83.4 mmol) were added to 300ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 23.9g of compound 24 was obtained. (yield 60%, MS: [ M+H)] + ＝717)
Synthesis example 25: production of Compound 25
First, in Synthesis example A-4-3, an intermediate compound A-3-1 was produced in the same manner as in Synthesis example A-4-3, except that 2-bromo-5-chloropyridine was used as a starting material instead of 4-bromo-2-chloropyridine.
Then, intermediate compound A-3-1 (15 g,55.6 mmol), amine 25 (22.1 g,55.6 mmol), sodium t-butoxide (8 g,83.4 mmol) were added to 300ml of xylene under nitrogen atmosphere, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 25.2g of compound 25 was obtained. (yield 72%, MS: [ M+H) ] + ＝631)
Synthesis example 26: production of Compound 26
First, in Synthesis example A-2-7, an intermediate compound A-2-9 was produced in the same manner as in Synthesis example A-4-3, except that (3- (methylthio) quinolin-2-yl) boric acid was used as a starting material instead of (6- (methylthio) isoquinolin-7-yl) boric acid.
Then, intermediate compound A-2-9 (15 g,55.6 mmol), amine 26 (22.8 g,55.6 mmol), sodium t-butoxide (8 g,83.4 mmol) were added to 300ml of xylene under nitrogen atmosphere, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 24.7g of compound 26 was obtained. (yield 69%, MS: [ M+H)] + ＝644)
Synthesis example 27: production of Compound 27
Intermediate compound A-2-7 (15 g,55.6 mmol), amine 27 (18.7 g,55.6 mmol), sodium tert-butoxide (8 g,83.4 mmol) were added to 300ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 19.9g of compound 27 was obtained. (yield 63%, MS: [ M+H) ] + ＝569)
Synthesis example 28: production of Compound 28
First, in Synthesis example A-1-6, an intermediate compound A-1-5 was produced in the same manner as in Synthesis example A-1-6, except that (7- (methylthio) quinolin-6-yl) boric acid was used as a starting material instead of (7- (methylthio) isoquinolin-6-yl) boric acid.
Then, intermediate compound A-1-5 (15 g,55.6 mmol), amine 28 (19.5 g,55.6 mmol), sodium t-butoxide (8 g,83.4 mmol) were added to 300ml of xylene under nitrogen atmosphere, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 21.1g of compound 28 was obtained. (yield 65%, MS: [ M+H ]] + ＝585)
Synthesis example 29: production of Compound 29
Intermediate compound A-3-5 (15 g,55.6 mmol) and amine 29 (21.3 g,58.4 mmol) were added to 300ml THF, stirred and refluxed. Then, potassium carbonate (23.1 g,166.8 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was added thereto. After 4 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 18.8g of compound 29 was produced. (yield 62%, MS: [ M+H) ] + ＝545)
Synthesis example 30: production of Compound 30
Intermediate compound A-4-3 (15 g,55.6 mmol) and amine 30 (24 g,58.4 mmol) were added to 300ml THF, stirred and refluxed. Then, potassium carbonate (23.1 g,166.8 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was added thereto. After 3 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 25g of compound 30 was produced. (yield 70%, MS: [ M+H)] + ＝644)
Comparative example 1
To Indium Tin Oxide (ITO)The glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.
On the ITO transparent electrode thus prepared, as a hole injection layer, the following HI-1 compound was usedAnd p-doping of the following a-1 compound was performed at a concentration of 1.5%. On the hole injection layer, the following HT-1 compound was subjected to vacuum evaporation to form a film thickness +.>Is provided. Next, on the hole transport layer, the film thickness is +.>An electron blocking layer was formed by vacuum evaporation of the EB-1 compound described below. Next, on the EB-1 plating film, the RH-1 compound and the Dp-39 compound were vacuum-deposited at a weight ratio of 98:2 to formA red light emitting layer of thickness. On the above-mentioned light-emitting layer, the film thickness is +.>The hole blocking layer was formed by vacuum evaporation of the HB-1 compound described below. Then, on the hole blocking layer, the following ET-1 compound and the following LiQ compound were vacuum-evaporated at a weight ratio of 2:1, thereby giving>Form an electron injection and transport layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added +.>Is made of aluminum +.>And vapor deposition is performed to form a cathode.
In the above process, the vapor deposition rate of the organic matter is maintained Lithium fluoride maintenance of cathode/sec->Vapor deposition rate per second, aluminum maintenance->Vapor deposition rate per second, vacuum degree was maintained at 2X 10 during vapor deposition -7 ～5×10 -6 The support is thus fabricated into an organic light emitting device. />
Comparative examples 2 to 6
The same procedure as in comparative example 1 was conducted except that the following compounds RH-2 to RH-6 were used as the main material of the red light emitting layer instead of RH-1, respectively, and the device performance was measured.
Examples 1 to 30
The same procedure as in comparative example 1 was conducted except that the compounds 1 to 30 produced in the synthesis example were used as the host material of the red light-emitting layer instead of the compound of comparative example 1, respectively, and the device performance was measured.
The driving voltage, current efficiency and lifetime of the organic light-emitting devices manufactured using the respective compounds as red host materials as in the above comparative examples 1 to 6 and examples 1 to 30 were measured, and the results thereof are shown in table 1 below.
TABLE 1
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Referring to table 1 above, it is apparent that the organic light emitting device of the example using the compound represented by chemical formula 1 above as a red host material exhibits a reduced driving voltage, and improved efficiency and lifetime characteristics, as compared to the organic light emitting device of the comparative example using a compound having a different structure from that of the organic light emitting device.
[ description of the symbols ]
1: substrate 2: anode
3: light emitting layer 4: cathode electrode
5: hole injection layer 6: hole transport layer
7: light emitting layer 8: electron injection and transport layers.
Claims (11)
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,
X 1 to X 4 One of them is CR, the others are each independently N, CH or CD,
wherein R is a substituent represented by the following chemical formula 2,
X 5 to X 10 Each independently is N, CH or CD,
however, X is 1 To X 10 One of which is N,
[ chemical formula 2]
In the chemical formula 2 described above, the chemical formula,
L 1 is a direct bond; substituted or unsubstituted C 6-60 Arylene groups; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 A heteroarylene group,
L 2 is a direct bond; substituted or unsubstituted C 6-60 Arylene groups; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 A heteroarylene group,
L 3 is a direct bond; substituted or unsubstituted C 6-60 Arylene groups; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 A heteroarylene group,
Ar 1 is substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 A heteroaryl group, which is a group,
Ar 2 is substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 Heteroaryl groups.
2. The compound of claim 1, wherein X 1 To X 4 One of them is CR, the other is N, the others are each independently CH or CD, X 5 To X 10 Each independently CH or CD, or
X 1 To X 4 One of them is CR and the others are each independently CH or CD, X 5 To X 10 One of them is N and the others are each independently CH or CD.
3. The compound of claim 1, wherein L 1 In order to be directly bonded or phenylene,
L 1 in the case of phenylene, it is unsubstituted or substituted with more than 1 deuterium.
4. The compound of claim 1, wherein L 2 Is a direct bond, phenylene, naphthylene, biphenylene, 9-dimethyl-fluorenylene, or 9, 9-diphenyl-fluorenylene,
L 2 in the case of phenylene, naphthylene, biphenylene, 9-dimethyl-fluorenylene, or 9, 9-diphenyl-fluorenylene, they are unsubstituted or substituted with more than 1 deuterium.
5. The compound of claim 1, wherein L 3 Is a direct bond, phenylene, naphthylene, biphenylene, 9-dimethyl-fluorenylene, or 9, 9-diphenyl-fluorenylene,
L 3 In the case of phenylene, naphthylene, biphenylene, 9-dimethyl-fluorenylene, or 9, 9-diphenyl-fluorenylene, they are unsubstituted or substituted with more than 1 deuterium.
6. The compound of claim 1, wherein Ar 1 Is phenyl, biphenyl, terphenyl, naphthyl, 9-dimethyl-fluorenyl, 9-diphenyl-fluorenyl, dibenzofuranyl, dibenzothienyl, 9-phenyl-carbazolyl, or 9,9' -spirodi [ 9H-fluorenyl ]]The base group of the modified polyester resin is a modified polyester resin,
wherein Ar is 1 Unsubstituted or substituted with more than 1 deuterium.
7. The compound of claim 1, wherein Ar 2 Is phenyl, biphenyl, terphenyl, naphthyl, 9-dimethyl-fluorenyl, 9-diphenyl-fluorenyl, dibenzofuranyl, dibenzothienyl, 9-phenyl-carbazolyl, or 9,9' -spirodi [ 9H-fluorenyl ]]The base group of the modified polyester resin is a modified polyester resin,
Ar 2 unsubstituted or substituted with more than 1 deuterium.
8. The compound according to claim 1, wherein the compound is represented by any one of the following chemical formulas 1-1 to 1-4:
[ chemical formula 1-1]
In the chemical formula 1-1 described above,
X 2 to X 10 One of which is N, the remainder each independently being CH or CD,
L 1 to L 3 、Ar 1 And Ar is a group 2 As defined in claim 1,
[ chemical formulas 1-2]
In the chemical formula 1-2 described above,
X 1 And X 3 To X 10 One of which is N, the remainder each independently being CH or CD,
L 1 to L 3 、Ar 1 And Ar is a group 2 As defined in claim 1,
[ chemical formulas 1-3]
In the chemical formulas 1 to 3 described above,
X 1 、X 2 and X 4 To X 10 One of which is N, the remainder each independently being CH or CD,
L 1 to L 3 、Ar 1 And Ar is a group 2 As defined in claim 1,
[ chemical formulas 1-4]
In the chemical formulas 1 to 4 described above,
X 1 to X 3 And X 5 To X 10 One of which is N, the remainder each independently being CH or CD,
L 1 to L 3 、Ar 1 And Ar is a group 2 As defined in claim 1.
9. The compound according to claim 1, wherein the compound represented by chemical formula 1 is any one selected from the group consisting of:
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10. an organic light emitting device, comprising: a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, the organic layer comprising the compound according to any one of claims 1 to 9.
11. The organic light-emitting device according to claim 10, wherein the organic layer containing the compound is a light-emitting layer.
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