CN116997554A - 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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- CN116997554A CN116997554A CN202280022665.5A CN202280022665A CN116997554A CN 116997554 A CN116997554 A CN 116997554A CN 202280022665 A CN202280022665 A CN 202280022665A CN 116997554 A CN116997554 A CN 116997554A
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- 239000011133 lead Substances 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
- 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
- 125000002560 nitrile group Chemical group 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
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 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
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229910052697 platinum Inorganic materials 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
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 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
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 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
- 238000007873 sieving Methods 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
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 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
- 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
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- Electroluminescent Light Sources (AREA)
Abstract
The present application 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. 10-2021-0153680 at 10 at 11 months of 2021 and korean patent application No. 10-2022-0147816 at 8 at 11 months of 2022, the entire contents of the disclosures of which are incorporated herein as part of the present specification.
The present application 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.
Prior art literature
Patent literature
(patent document 1) Korean patent laid-open No. 10-2000-0051826
Disclosure of Invention
Technical problem
The present invention relates to a novel organic light emitting material and an organic light emitting device including 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 10 Any one of which is N, the rest are CR,
each of the above R is independently hydrogen, deuterium, or a substituent represented by the following chemical formula 2,
[ chemical formula 2]
In the above-mentioned chemical formula 2,
Ar 1 and Ar is a group 2 Each independently is a substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O and S 2-60 Heteroaryl, but excluding biphenyl substituted with methoxy,
L 1 to L 3 Each independently is a single bond; substituted or unsubstituted C 6-60 Arylene groups; or substituted or unsubstituted C comprising any one or more selected from N, O and S 2-60 Heteroarylene group.
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 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.
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, light emission, electron transport, and/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 composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a cathode 4
Detailed Description
In the following, the invention will be described in more detail in order to aid understanding thereof.
The present invention provides a compound represented by the above chemical formula 1.
In the present description of the invention,represents a bond to other substituents.
In the present specification, the term "substituted or unsubstituted" means that it is selected from deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; alkylthio group Arylthio->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 1 or more substituents in heteroaryl group containing N, O and 1 or more of S atoms are substituted or unsubstituted, or are linked by 2 or more substituents among the above exemplified substituentsThe resulting substituent 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 substituent 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 substituent may be a substituent 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 substituent 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. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, and the like,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 beAnd the like, but 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. According to one embodiment, the heteroaryl group has 6 to 30 carbon atoms. According to one embodiment, the heteroaryl group has 6 to 20 carbon atoms. Examples of heteroaryl groups include 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, and the arylamine 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, the heteroaryl group is not a 1-valent group, but a combination of 2 substituents, and the above description of the heteroaryl group can be applied.
Preferably, the above chemical formula 1 may be represented by any one of the following chemical formulas 1-1 to 1-10:
in the above chemical formulas 1-1 to 1-10,
r is as defined in chemical formula 1 above.
Preferably, in the above chemical formula 1, any one of R is a substituent represented by the above chemical formula 2, and the rest may be hydrogen or deuterium. More preferably, any one of R is a substituent represented by the above chemical formula 2, and the rest may be hydrogen.
Preferably Ar 1 And Ar is a group 2 Each independently may be substituted or unsubstituted C 6-30 An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O and S 2-30 Heteroaryl, but not biphenyl substituted with methoxy. More preferably Ar 1 And Ar is a group 2 Each independently may be phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, dibenzofuranyl, dibenzothiophenyl or phenylcarbazolyl, ar as described above 1 And Ar is a group 2 May be unsubstituted or substituted with more than 1 deuterium. Most preferably Ar 1 And Ar is a group 2 Each independently may be any one selected from the group consisting of:
preferably L 1 To L 3 Each independently may be a single bond; substituted or unsubstituted C 6-20 Arylene groups; or substituted or unsubstituted C comprising any one or more selected from N, O and S 2-20 Heteroarylene group. More preferably L 1 To L 3 Each independently may be a single bond, phenylene, naphthalenediyl, dimethylfluorendiyl, diphenylfluorendiyl or carbazoldiyl, L 1 To L 3 In the case of phenylene, naphthalenediyl, dimethylfluorendiyl, diphenylfluorendiyl or carbazoldiyl, L 1 To L 3 May be unsubstituted or substituted with more than 1 deuterium. Most preferably L 1 To L 3 Each independently canTo be a single bond, or to be any one selected from the group consisting of:
preferably L 1 May be a single bond or a phenylene group which is unsubstituted or substituted with 1 or more deuterium.
Representative examples of the compounds represented by the above chemical formula 1 are shown below:
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x in the compound represented by the above chemical formula 1 1 Is N, X 2 X is a substituent represented by the formula 2 3 To X 10 Is CR, L 1 When not a single bond, the compound may be produced by the following production method shown in reaction 1, X, as an example 1 Is N, X 2 X is a substituent represented by the formula 2 3 To X 10 Is CR, L 1 In the case of a single bond, the production method shown in the following reaction formula 2 is one example, and other compounds may be similarly produced, except that the production method is also one.
[ reaction type 1]
[ reaction type 2]
R, L in the above equations 1 and 2 2 、L 3 、Ar 1 And Ar is a group 2 With the above-mentioned formula 1Meaning the same, Z 1 And Z 2 Each independently is halogen, preferably Z 1 And Z 2 Each independently is chlorine or bromine.
The reaction formula 1 is a suzuki coupling reaction, preferably in the presence of a palladium catalyst and a base, and the reactive groups for the suzuki coupling reaction may be modified according to techniques known in the art. In addition, the above reaction formula 2 is an amine substitution reaction, preferably performed in the presence of a palladium catalyst and a base, and the reactive group for the amine substitution reaction may be changed according to a technique known in the art. The above-described production method can be more specifically described in the production example described later.
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, 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 light-emitting layer, and the light-emitting layer may include a compound represented by chemical formula 1.
The organic layer may include a hole transporting layer, a hole injecting layer, a layer that performs hole transport and hole injection simultaneously, or an electron blocking layer, and the hole transporting layer, the hole injecting layer, the layer that performs hole transport and hole injection simultaneously, or the electron blocking layer may include a compound represented by chemical formula 1. Preferably, the hole transport layer, the hole injection layer, or the electron blocking layer may include a compound represented by chemical formula 1. More preferably, the electron blocking layer may include a compound represented by 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, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above hole injection layer, hole transport layer, electron blocking layer, or light emitting layer. Preferably, the compound represented by the above chemical formula 1 may be contained in the above hole injection layer, hole transport layer, or electron blocking layer. More preferably, the compound represented by the above chemical formula 1 may be contained in the above electron blocking 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 a first electrode, an organic layer, and a second electrode 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 polymers such as (PEDOT), polypyrrole and polyaniline, but 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 polymers.
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 polymers, and block copolymers having both conjugated and unconjugated portions.
The electron blocking 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 being recombined in the light emitting layer. The electron blocking layer is preferably a substance having a smaller electron affinity than the electron transport layer. Preferably, a compound represented by the above chemical formula 1 may be included as a substance of the electron blocking layer.
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. As a toolExamples thereof include 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 light emitting layer may include a host material and a dopant material. The host material includes aromatic condensed ring derivatives, heterocyclic compounds, and the like. 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, ladder-type furan compounds, pyrimidine derivatives, and the like, 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,And bisindenopyrene, etc., wherein the 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 2 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. As an example, any one or more selected from the following group may be used as the dopant material, but is not limited thereto:
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The hole blocking layer is a layer interposed between the electron transport layer and the light emitting layer, and is also called a hole suppressing layer, in order to prevent holes injected from the anode from being transferred to the electron transport layer without being recombined in the light emitting layer. The hole blocking layer is preferably a substance having a large ionization energy.
The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and the electron transporting substance is a substance that can well receive electrons from the cathode and transfer the electrons to the light emitting layer, and is preferably a substance having high mobility for electrons. 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. Specifically 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 "hole injection and transport layer" is a layer that functions as both the hole injection layer and the hole transport layer, and the materials that function as the layers may be used singly or in combination.
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 represented by the above chemical formula 1 may be included 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 described in the following synthesis examples and 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.
Production example 1
5-bromo-2-chloropyridin-4-amine (5-bromo2-chloropyridin-4-amine) (15 g,72.3 mmol) and (2-methoxynaphthalen-1-yl) boronic acid ((2-me)Thoxyaphthalen-1-yl) acrylic acid (15.3 g,75.9 mmol) was added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (potassium carbonate) (30 g,216.9 mmol) was dissolved in 100ml of water and the mixture was poured, and after stirring the mixture sufficiently, bis (tri-tert-butylphosphine) palladium (0) (bis (tris-tert-butylphosphine) palladium (0)) (0.4 g,0.7 mmol) was poured. 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 14g of compound A-1-1_P1 was produced. (yield 68%, MS: [ M+H) ] + ＝285)
Compound A-1-1_P1 (15 g,52.7 mmol) and HBF 4 (9.3 g,105.4 mmol) was added to 150ml of Acetonitrile (Acetonitile) and stirred. Then, naNO is added 2 (14.6 g,105.4 mmol) was dissolved in 30ml of water and added slowly at 0 ℃. After the reaction for 8 hours, the temperature was raised to room temperature, and 300ml of water was added thereto for dilution. After 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 6.9g of compound A-1-1 was produced. (yield 52%, MS: [ M+H)] + ＝254)
Production example 2
4-bromopyridin-3-amine (4-bromoxyndin-3-amine) (15 g,86.7 mmol) and (4-chloro-2-methoxynaphthalen-1-yl) boronic acid ((4-chloro-2-methoxynaphthalen-1-yl) carboxylic acid) (21.5 g,91 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (35.9 g,260.1 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.4 g,0.9 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. Dissolving in chloroform again, washing with water for 2 times, separating organic layer, adding anhydrous magnesium sulfate, stirring, and sieving Filtering, and distilling the filtrate under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 16.5g of compound A-2-4_P1 was produced. (yield 67%, MS: [ M+H)] + ＝285)
Compound A-2-4_P1 (15 g,52.7 mmol) and HBF 4 (9.3 g,105.4 mmol) was added to 150ml of acetonitrile and stirred. Then, naNO is added 2 (14.6 g,105.4 mmol) was dissolved in 30ml of water and added slowly at 0 ℃. After 10 hours of reaction, the temperature was raised to room temperature, and 300ml of water was added to dilute the mixture. After 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 6.7g of compound A-2-4 was produced. (yield 50%, MS: [ M+H)] + ＝254)
Production example 3
3-bromopyridin-2-amine (3-bromopyridin-2-amine) (15 g,86.7 mmol) and (5-chloro-2-methoxynaphthalen-1-yl) boronic acid ((5-chloro-2-methoxynaphthalen-1-yl) carboxylic acid) (21.5 g,91 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (35.9 g,260.1 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.4 g,0.9 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 17.7g of compound A-3-5_P1 was produced. (yield 72%, MS: [ M+H) ] + ＝285)
Compound A-3-5_P1 (15 g,52.7 mmol) and HBF 4 (9.3 g,105.4 mmol) was added to 150ml of acetonitrile and stirred. Then, naNO is added 2 (14.6 g,105.4 mmol) was dissolved in 30ml of water and added slowly at 0 ℃. After 9 hours of reaction, the temperature was raised to room temperature, and 300ml of water was added to dilute the mixture. Dissolving in chloroform, washing with waterAfter 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 7.1g of compound A-3-5 was produced. (yield 53%, MS: [ M+H)] + ＝254)
Production example 4
2-bromopyridin-3-amine (2-bromopyrindin-3-amine) (15 g,86.7 mmol) and (5-chloro-2-methoxynaphthalen-1-yl) boric acid (21.5 g,91 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (35.9 g,260.1 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.4 g,0.9 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 17.2g of compound A-4-6_P1 was produced. (yield 70%, MS: [ M+H) ] + ＝285)
Compound A-4-6_P1 (15 g,52.7 mmol) and HBF 4 (9.3 g,105.4 mmol) was added to 150ml of acetonitrile and stirred. Then, naNO is added 2 (14.6 g,105.4 mmol) was dissolved in 30ml of water and added slowly at 0 ℃. After 10 hours of reaction, the temperature was raised to room temperature, and 300ml of water was added to dilute the mixture. After 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 9.7g of compound A-4-6 was produced. (yield 73%, MS: [ M+H)] + ＝254)
Production example 5
2-bromo-6-chloroaniline (2-bromoo-6-chloroaniline) (15 g)72.6 mmol) and (3-methoxyisoquinolin-4-yl) boronic acid ((3-methoxyisoquinolin-4-yl) boronicacid) (15.5 g,76.3 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (30.1 g,217.9 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.4 g,0.7 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 13.8g of compound A-5-3_P1 was produced. (yield 67%, MS: [ M+H) ] + ＝285)
Compound A-5-3_P1 (15 g,52.7 mmol) and HBF 4 (9.3 g,105.4 mmol) was added to 150ml of acetonitrile and stirred. Then, naNO is added 2 (14.6 g,105.4 mmol) was dissolved in 30ml of water and added slowly at 0 ℃. After 10 hours of reaction, the temperature was raised to room temperature, and 300ml of water was added to dilute the mixture. After 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 8.3g of compound A-5-3 was produced. (yield 62%, MS: [ M+H)] + ＝254)
Production example 6
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2-Bromoaniline (15 g,87.2 mmol) and (7-chloro-3-methoxyquinolin-4-yl) boronic acid (7-chloro-3-methoxyquinin-4-yl) were added to 300ml of THF, and stirred and refluxed. Then, potassium carbonate (36.2 g,261.6 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.4 g,0.9 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 18.6g of compound A-6-6_P1 was produced. (yield 75%, MS: [ M+H)] + ＝285)
Compound A-6-6_P1 (15 g,52.7 mmol) and HBF 4 (9.3 g,105.4 mmol) was added to 150ml of acetonitrile and stirred. Then, naNO is added 2 (14.6 g,105.4 mmol) was dissolved in 30ml of water and added slowly at 0 ℃. After the reaction for 8 hours, the temperature was raised to room temperature, and 300ml of water was added thereto for dilution. After 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 7.7g of compound A-6-6 was produced. (yield 58%, MS: [ M+H)] + ＝254)
PREPARATION EXAMPLE 7
2-Bromoaniline (15 g,87.2 mmol) and (7-chloro-6-methoxyquinolin-5-yl) boronic acid (7-chloro-6-methoxyquinin-5-yl) are added to 300ml of THF (21.7 g,91.5 mmol), stirred and refluxed. Then, potassium carbonate (36.2 g,261.6 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.4 g,0.9 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 18.1g of compound A-7-4_P1 was produced. (yield 73%, MS: [ M+H) ] + ＝285)
Compound A-7-4_P1 (15 g,52.7 mmol) and HBF 4 (9.3 g,105.4 mmol) was added to 150ml of acetonitrile and stirred. Then, naNO is added 2 (14.6 g,105.4 mmol) was dissolved in 30ml of water and added slowly at 0 ℃. After 10 hours of reaction, the temperature was raised to room temperature, and 300ml of water was added to dilute the mixture. Dissolving in chloroform, washing with water for 2 times, separating organic layer, adding anhydrous magnesium sulfate, stirringAfter filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 7.9g of compound A-7-4 was produced. (yield 59%, MS: [ M+H)] + ＝254)
Production example 8
2-Bromoaniline (15 g,87.2 mmol) and (3-chloro-6-methoxyisoquinolin-5-yl) boronic acid (3-chloro-6-methoxyisoquinolin-5-yl) acid) (21.7 g,91.5 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (36.2 g,261.6 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.4 g,0.9 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 18.3g of compound A-8-7_P1 was produced. (yield 74%, MS: [ M+H ] ] + ＝285)
Compound A-8-7_P1 (15 g,52.7 mmol) and HBF 4 (9.3 g,105.4 mmol) was added to 150ml of acetonitrile and stirred. Then, naNO is added 2 (14.6 g,105.4 mmol) was dissolved in 30ml of water and added slowly at 0 ℃. After the reaction for 8 hours, the temperature was raised to room temperature, and 300ml of water was added thereto for dilution. After 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 6.7g of compound A-8-7 was produced. (yield 50%, MS: [ M+H)] + ＝254)
Production example 9
2-bromo-4-chloroaniline (2-bromoo-4-chloroaniline) (15 g,72.6 mmol) and (7-methoxyisoquinoline8-yl) boronic acid ((7-methoysisoquin-8-yl) carboxylic acid) (15.5 g,76.3 mmol) was added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (30.1 g,217.9 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.4 g,0.7 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 14.2g of compound A-9-1_P1 was produced. (yield 69%, MS: [ M+H) ] + ＝285)
Compound A-9-1_P1 (15 g,52.7 mmol) and HBF 4 (9.3 g,105.4 mmol) was added to 150ml of acetonitrile and stirred. Then, naNO is added 2 (14.6 g,105.4 mmol) was dissolved in 30ml of water and added slowly at 0 ℃. After 10 hours of reaction, the temperature was raised to room temperature, and 300ml of water was added to dilute the mixture. After 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 9.9g of compound A-9-1 was produced. (yield 74%, MS: [ M+H ]] + ＝254)
Production example 10
2-Bromoaniline (15 g,87.2 mmol) and (5-chloro-7-methoxyquinolin-8-yl) boronic acid (5-chloro-7-methoxyquin-8-yl) are added to 300ml of THF (21.7 g,91.5 mmol), stirred and refluxed. Then, potassium carbonate (36.2 g,261.6 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.4 g,0.9 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. Subjecting the concentrated compound to silica gel column chromatography Thus, 18.1g of Compound A-10-5_P1 was produced. (yield 73%, MS: [ M+H)] + ＝285)
Compound A-10-5_P1 (15 g,52.7 mmol) and HBF 4 (9.3 g,105.4 mmol) was added to 150ml of acetonitrile and stirred. Then, naNO is added 2 (14.6 g,105.4 mmol) was dissolved in 30ml of water and added slowly at 0 ℃. After the reaction for 8 hours, the temperature was raised to room temperature, and 300ml of water was added thereto for dilution. After 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 8.4g of compound A-10-5 was produced. (yield 63%, MS: [ M+H)] + ＝254)
The precursor substances other than the precursor compounds synthesized in the above production examples 1 to 10 were obtained by different intermediates and by synthesis by the methods described above. The obtained precursor materials were used to produce the compounds of the synthesis examples described below.
Synthesis example 1
Compound A-4-8 (15 g,59.1 mmol) and compound amine (amine) 1 (32.5 g,62.1 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (24.5 g,177.3 mmol) was dissolved in 100ml of water and the mixture was poured, and after stirring the mixture sufficiently, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 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 25.8g of compound 1 was produced. (yield 71%, MS: [ M+H) ] + ＝615)
Synthesis example 2
Compound A-4-3 (15 g,59.1 mmol), compound amine 2 (18.3 g,62.1 mmol), sodium tert-butoxide (7.4 g,76.8 mmol) were added to 300ml of Xylene (Xylene) under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 4 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 20.6g of compound 2 was obtained. (yield 68%, MS: [ M+H)] + ＝513)
Synthesis example 3
Compound A-4-1 (15 g,59.1 mmol), compound amine 3 (22.4 g,62.1 mmol), sodium tert-butoxide (7.4 g,76.8 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, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 23.6g of compound 3 was obtained. (yield 69%, MS: [ M+H) ] + ＝579)
Synthesis example 4
Compound A-1-3 (15 g,59.1 mmol), compound amine 4 (22.4 g,62.1 mmol), sodium tert-butoxide (7.4 g,76.8 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, at the end of the reaction, cooling to normalThe solvent was removed by warm and reduced pressure. 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, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 20.9g of compound 4 was obtained. (yield 61%, MS: [ M+H)] + ＝579)
Synthesis example 5
Compound A-1-1 (15 g,59.1 mmol), compound amine 5 (20 g,62.1 mmol), sodium tert-butoxide (7.4 g,76.8 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 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 21g of compound 5 was obtained. (yield 66%, MS: [ M+H) ] + ＝539)
Synthesis example 6
Compound A-1-5 (15 g,59.1 mmol), compound amine 6 (23.7 g,62.1 mmol), sodium tert-butoxide (7.4 g,76.8 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 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 24.8g of compound 6 was obtained. (yield 70%, MS: [ M+H)] + ＝599)
Synthesis example 7
Compound A-2-7 (15 g,59.1 mmol), compound amine 7 (21.7 g,62.1 mmol), sodium tert-butoxide (7.4 g,76.8 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, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 24.8g of compound 7 was obtained. (yield 74%, MS: [ M+H ] ] + ＝567)
Synthesis example 8
Compound A-2-7 (15 g,59.1 mmol), compound amine 8 (25.5 g,62.1 mmol), sodium tert-butoxide (7.4 g,76.8 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, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 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 26.7g of compound 8 was obtained. (yield 72%, MS: [ M+H)] + ＝628)
Synthesis example 9
Compound A-2-5 (15 g,59.1 mmol) and compound amine 9 (30.9 g,62.1 mmol) were added to 300ml of THF, stirred andand (5) refluxing. Then, potassium carbonate (24.5 g,177.3 mmol) was dissolved in 100ml of water and the mixture was poured, and after stirring the mixture sufficiently, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 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 26.1g of compound 9 was produced. (yield 75%, MS: [ M+H) ] + ＝589)
Synthesis example 10
Compound A-2-2 (15 g,59.1 mmol), compound amine 10 (23.1 g,62.1 mmol), sodium tert-butoxide (7.4 g,76.8 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, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 21.9g of compound 10 was obtained. (yield 63%, MS: [ M+H)] + ＝589)
Synthesis example 11
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Compound A-2-1 (15 g,59.1 mmol), compound amine 11 (24.7 g,62.1 mmol), sodium tert-butoxide (7.4 g,76.8 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 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and the organic layer was separated and treated with anhydrous magnesium sulfateAfter filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 26.1g of compound 11 was obtained. (yield 72%, MS: [ M+H) ] + ＝615)
Synthesis example 12
Compound A-3-7 (15 g,59.1 mmol), compound amine 12 (20.8 g,62.1 mmol), sodium tert-butoxide (7.4 g,76.8 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, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 24.5g of compound 12 was obtained. (yield 75%, MS: [ M+H)] + ＝553)
Synthesis example 13
Compound A-3-8 (15 g,59.1 mmol), compound amine 13 (24.7 g,62.1 mmol), sodium tert-butoxide (7.4 g,76.8 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, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 22.5g of compound 13 was obtained. (yield 62%, MS: [ M+H) ] + ＝615)
Synthesis example 14
Compound A-5-2 (15 g,59.1 mmol), compound amine 14 (25.5 g,62.1 mmol), sodium tert-butoxide (7.4 g,76.8 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 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 22.7g of compound 14 was obtained. (yield 61%, MS: [ M+H)] + ＝629)
Synthesis example 15
Compound A-5-7 (15 g,59.1 mmol) and compound amine 15 (34.4 g,62.1 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (24.5 g,177.3 mmol) was dissolved in 100ml of water and the mixture was poured, and after stirring the mixture sufficiently, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 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 24g of compound 15 was produced. (yield 63%, MS: [ M+H) ] + ＝645)
Synthesis example 16
Compound A-6-2 (15 g,59.1 mmol), compound amine 16 (30.1 g,62.1 mmol), sodium tert-butoxide (7.4 g,76.8 mmol) were added to 300ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) is addedPalladium (0) (0.3 g,0.6 mmol). After 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 29.1g of compound 16 was obtained. (yield 70%, MS: [ M+H)] + ＝703)
Synthesis example 17
Compound A-6-7 (15 g,59.1 mmol), compound amine 17 (24.7 g,62.1 mmol), sodium tert-butoxide (7.4 g,76.8 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 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 22.9g of compound 17 was obtained. (yield 63%, MS: [ M+H) ] + ＝615)
Synthesis example 18
Compound A-7-2 (15 g,59.1 mmol) and compound amine 18 (30.9 g,62.1 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (24.5 g,177.3 mmol) was dissolved in 100ml of water and the mixture was poured, and after stirring the mixture sufficiently, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 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. Purifying the concentrated compound by silica gel column chromatography to obtain21.6g of compound 18 were produced. (yield 62%, MS: [ M+H)] + ＝589)
Synthesis example 19
Compound A-7-4 (15 g,59.1 mmol), compound amine 19 (22.7 g,62.1 mmol), sodium tert-butoxide (7.4 g,76.8 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, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 23.1g of compound 19 was obtained. (yield 67%, MS: [ M+H) ] + ＝583)
Synthesis example 20
Compound A-7-1 (15 g,59.1 mmol), compound amine 20 (23.1 g,62.1 mmol), sodium tert-butoxide (7.4 g,76.8 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, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 24.7g of compound 20 was obtained. (yield 71%, MS: [ M+H)] + ＝589)
Synthesis example 21
Compound A-8-1 (15 g,59.1 mmol), compound amine 21 (26.2 g,62.1 mmol), sodium tert-butoxide (7.4 g,76.8 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, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 28.3g of compound 21 was obtained. (yield 75%, MS: [ M+H) ] + ＝639)
Synthesis example 22
Compound A-8-5 (15 g,59.1 mmol), compound amine 22 (30.1 g,62.1 mmol), sodium tert-butoxide (7.4 g,76.8 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 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 31.1g of compound 22 was obtained. (yield 75%, MS: [ M+H)] + ＝703)
Synthesis example 23
Compound A-9-1 (15 g,59.1 mmol) and compound amine 23 (29.6 g,62.1 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (24.5 g,177.3 mmol) was dissolved in 100ml of water and the mixture was poured, and after stirring the mixture sufficiently, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was poured. After 5 hours of reaction, the mixture is cooled to normal temperature, and the organic layer and the water layer are separated and steamedThe organic layer was 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 24.1g of compound 23 was produced. (yield 73%, MS: [ M+H) ] + ＝559)
Synthesis example 24
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Compound A-9-5 (15 g,59.1 mmol), compound amine 24 (30 g,62.1 mmol), sodium tert-butoxide (7.4 g,76.8 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 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 28.2g of compound 24 was obtained. (yield 68%, MS: [ M+H)] + ＝701)
Synthesis example 25
Compound A-9-4 (15 g,59.1 mmol) and compound amine 25 (27.8 g,62.1 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (24.5 g,177.3 mmol) was dissolved in 100ml of water and the mixture was poured, and after stirring the mixture sufficiently, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 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 23.9g of compound 25 was produced. (yield 75%, MS: [ M+H) ] + ＝539)
Synthesis example 26
Compound A-10-2 (15 g,59.1 mmol), compound amine 26 (20 g,62.1 mmol), sodium tert-butoxide (7.4 g,76.8 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, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 20.4g of compound 26 was obtained. (yield 64%, MS: [ M+H)] + ＝539)
Synthesis example 27
Compound A-10-7 (15 g,59.1 mmol), compound amine 27 (21.4 g,62.1 mmol), sodium tert-butoxide (7.4 g,76.8 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, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 23.9g of compound 27 was obtained. (yield 72%, MS: [ M+H) ] + ＝563)
Synthesis example 28
Compound A-10-8 (15 g,59.1 mmol), compound amine 28 (26.5 g,62.1 mmol) was reacted under nitrogen atmosphereSodium tert-butoxide (7.4 g,76.8 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 4 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 24g of compound 28 was obtained. (yield 63%, MS: [ M+H)] + ＝645)
Synthesis example 29
Compound A-10-5 (15 g,59.1 mmol), compound amine 29 (25.5 g,62.1 mmol), sodium tert-butoxide (7.4 g,76.8 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, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 24.1g of compound 29 was obtained. (yield 65%, MS: [ M+H ] ] + ＝628)
Example 1
To ITO (indium tin oxide)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 finished, the distilled water washing is carried out by using solvents of isopropanol, acetone and methanolAfter ultrasonic washing and drying, the mixture is 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 compound HI-1 was usedAnd the following compound a-1 was p-doped (p-dopping) at a concentration of 1.5 wt.%. On the hole injection layer, the following compound HT-1 was vacuum evaporated to form a film thickness +.>Is provided. Next, on the hole transport layer, the film thickness is +.>The compound 1 produced as described above was vacuum-evaporated to form an electron blocking layer. Next, on the above-mentioned compound 1, vacuum evaporation was performed with the following compound RH-1 as a main body and the following compound Dp-7 as a dopant in a weight ratio of 98:2, thereby forming +. >A 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 following compound HB-1. 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 the thickness of the substrate, thereby forming a cathode.
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In the above process, the vapor deposition rate of the organic matter is maintainedLithium fluoride maintenance of cathode>Is kept at>Is to maintain a vacuum degree of 2 x 10 during vapor deposition -7 ～5*10 -6 The support is thus fabricated into an organic light emitting device.
Examples 2 to 29
An organic light-emitting device was manufactured in the same manner as in example 1 above, except that the compound 1 was replaced with the compound described in table 1 below in the organic light-emitting device of example 1.
Comparative examples 1 to 6
An organic light-emitting device was manufactured in the same manner as in comparative example 1 above, except that the compound 1 was replaced with the compound described in table 1 below in the organic light-emitting device of example 1. The structures of the compounds C-1 to C-6 of Table 1 are shown below.
Experimental example
For the above examples 1 to 29 and comparative examples 1 to comparative examplesWhen a current was applied to the organic light-emitting device manufactured in example 6, it was measured (15 mA/cm 2 ) The voltage and efficiency are shown in table 1 below. Lifetime T95 refers to the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.
TABLE 1
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The results of table 1 above were obtained when current was applied to the organic light emitting devices fabricated according to examples 1 to 29 and comparative examples 1 to 6. As a material constituting the red organic light emitting device of example 1, a material widely used in the past was used, and the compound Dp-7 was used as a dopant for the red light emitting layer.
Comparative examples 1 to 6 organic light emitting devices were manufactured using C-1 to C-6 instead of compound 1. From the results of table 1, it is clear that the compound of the present invention, when used as an electron blocking layer, has a lower driving voltage and higher efficiency than those of the comparative example, and thus energy transfer from the host to the red dopant is satisfactory. In addition, it is found that the life characteristics can be greatly improved while maintaining high efficiency. This is considered to be due to the fact that the compound of the present invention has higher stability against electrons and holes than the compound of the comparative example.
From the above, it was confirmed that the use of the compound of the present invention as an electron blocking layer for a red light emitting layer can improve the driving voltage, light emitting efficiency and lifetime characteristics of an 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: electron blocking layer 8: hole blocking layer
9: electron injection and transport layers.
Claims (10)
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 10 Any one of which is N, the rest are CR,
each R is independently hydrogen, deuterium, or a substituent represented by the following chemical formula 2,
[ chemical formula 2]
In the chemical formula 2 described above, the chemical formula,
Ar 1 and Ar is a group 2 Each independently is a substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O and S 2-60 Heteroaryl, but excluding biphenyl substituted with methoxy,
L 1 to L 3 Each independently is a single bond; substituted or unsubstituted C 6-60 Arylene groups; or substituted or unsubstituted C comprising any one or more selected from N, O and S 2-60 Heteroarylene group.
2. The compound according to claim 1, wherein any one of R is a substituent represented by the chemical formula 2, and the remainder are hydrogen or deuterium.
3. The compound of claim 1, wherein Ar 1 And Ar is a group 2 Each independently is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, dibenzoFuryl, dibenzothienyl or phenylcarbazolyl,
the Ar is as follows 1 And Ar is a group 2 Unsubstituted or substituted with more than 1 deuterium.
4. The compound of claim 1, wherein Ar 1 And Ar is a group 2 Each independently is any one selected from the group consisting of:
5. the compound of claim 1, wherein L 1 To L 3 Each independently is a single bond, phenylene, naphthalenediyl, dimethylfluorendiyl, diphenylfluorendiyl or carbazoldiyl,
the L is 1 To L 3 In the case of phenylene, naphthalenediyl, dimethylfluorendiyl, diphenylfluorendiyl or carbazoldiyl, L 1 To L 3 Unsubstituted or substituted with more than 1 deuterium.
6. The compound of claim 1, wherein L 1 To L 3 Each independently is a single bond or any one selected from the group consisting of:
7. the compound of claim 1, wherein L 1 Is a single bond, or phenylene which is unsubstituted or substituted with more than 1 deuterium.
8. 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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9. An organic light emitting device, comprising: 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 the compound according to any one of claims 1 to 8.
10. The organic light-emitting device of claim 9, wherein the organic layer is a hole injection layer, a hole transport layer, or an electron blocking layer.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2021-0153680 | 2021-11-10 | ||
| KR1020220147816A KR20230069021A (en) | 2021-11-10 | 2022-11-08 | Novel compound and organic light emitting device comprising the same |
| KR10-2022-0147816 | 2022-11-08 | ||
| PCT/KR2022/017602 WO2023085789A1 (en) | 2021-11-10 | 2022-11-10 | Novel compound and organic light-emitting device comprising same |
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| Publication Number | Publication Date |
|---|---|
| CN116997554A true CN116997554A (en) | 2023-11-03 |
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| CN202280022665.5A Pending CN116997554A (en) | 2021-11-10 | 2022-11-10 | Novel compound and organic light emitting device comprising the same |
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