CN113939508A - Novel compound and organic light emitting device comprising same - Google Patents
Novel compound and organic light emitting device comprising same Download PDFInfo
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- CN113939508A CN113939508A CN202180003755.5A CN202180003755A CN113939508A CN 113939508 A CN113939508 A CN 113939508A CN 202180003755 A CN202180003755 A CN 202180003755A CN 113939508 A CN113939508 A CN 113939508A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 132
- 239000012044 organic layer Substances 0.000 claims description 206
- 239000010410 layer Substances 0.000 claims description 174
- 239000000126 substance Substances 0.000 claims description 158
- -1 dibenzofuranyl Chemical group 0.000 claims description 137
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 125000005878 benzonaphthofuranyl group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
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- 229910052805 deuterium Inorganic materials 0.000 claims description 5
- 125000005561 phenanthryl group Chemical group 0.000 claims description 5
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- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 2
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
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- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
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- 125000003282 alkyl amino group Chemical group 0.000 description 2
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- 125000004414 alkyl thio group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- HAQFCILFQVZOJC-UHFFFAOYSA-N anthracene-9,10-dione;methane Chemical compound C.C.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 HAQFCILFQVZOJC-UHFFFAOYSA-N 0.000 description 2
- 125000005264 aryl amine group Chemical group 0.000 description 2
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- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
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- 150000004696 coordination complex Chemical class 0.000 description 2
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- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
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- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
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- 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 2
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
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- 150000004866 oxadiazoles Chemical class 0.000 description 2
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- 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
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 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
- 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
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 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
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229960003540 oxyquinoline Drugs 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
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-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
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 125000003367 polycyclic group Chemical group 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
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
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- 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
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- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 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
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003577 thiophenes Chemical class 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
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 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
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000007738 vacuum evaporation 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
- 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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Abstract
The present invention provides a novel compound and an organic light emitting device including the same.
Description
Technical Field
Cross reference to related applications
The present application claims priority based on korean patent application No. 10-2020-0029229 at 9/2020 and korean patent application No. 10-2021-0029951 at 8/3/2021, the entire contents disclosed in the documents containing the korean patent application are incorporated herein by reference.
The present invention relates to a novel compound and an organic light emitting device 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, a fast response time, and excellent luminance, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.
An 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 the 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, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons (exiton) are formed, which emit light when they transition to the ground state again.
For organic materials used for the organic light emitting devices as described above, development of new materials is continuously demanded.
Documents of the prior art
Patent document
(patent document 1) Korean patent laid-open No. 10-2000-0051826
Disclosure of Invention
Technical subject
The present invention relates to a novel compound and an organic light emitting device comprising the same.
Means for solving the problems
The present invention provides a compound represented by the following chemical formula 1:
[ chemical formula 1]
In the above-described chemical formula 1,
R1and R2Each independently is substituted or unsubstituted C6-60Aryl, dibenzofuranyl or dibenzothiophenyl,
X1each independently is N or CH, and the above X1At least one of which is N,
Ar1and Ar2Each independently hydrogen, deuterium, unsubstituted C6-60Aryl group, or the following chemical formula 2,
[ chemical formula 2]
In the above-described chemical formula 2,
X2is O or S, and is a compound of,
R3to R10Any one of them is bound to the above chemical formula 1, and R not bound to the above chemical formula 13To R10Each independently hydrogen or deuterium, or may combine with an adjacent group to form an aromatic ring,
Ar1、Ar2、R1and R2At least one of which is naphthyl, phenylnaphthyl, naphthylphenyl, fluoranthenyl, benzonaphthofuranyl or benzonaphthothienyl.
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, low driving voltage, and/or improvement of life span 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, light emission, electron transport, or electron injection.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device composed of 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 suppression layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a cathode 4.
Detailed Description
Hereinafter, the present invention will be described in more detail to assist understanding thereof.
(definition of wording)
In the context of the present specification,
and
represents a bond to other substituents.
In the present specification, the term "substituted or unsubstituted" means substituted with a substituent selected from deuterium; a halogen group; a 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 (Alkyl thio); arylthio (Aryl thio); alkylsulfonyl (Alkyl sulfonyl); arylsulfonyl (Aryl sulfonyl); a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamino group; an aralkylamino group; a heteroaryl amino group; an arylamine group; an aryl phosphine group; or 1 or more substituents of 1 or more heteroaryl groups containing N, O and S atoms, or substituted or unsubstituted by 2 or more substituents of the above-exemplified substituents. For example, "a substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group 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, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.
In the present specification, the number of carbon atoms in 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, specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.
In the present specification, the boron group specifically includes a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like, but is not limited thereto.
In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.
In the present specification, the alkyl group may be linear or branched, 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 alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methylbutyl group, a 1-ethylbutyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, a n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3, 3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, a n-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, an octyl group, a n-octyl group, a tert-octyl group, a 1-methylheptyl group, a 2-ethylhexyl group, a 2-propylpentyl group, a n-nonyl group, a 2, 2-dimethylheptyl group, a 1-ethyl-propyl group, a 1, 1-dimethyl-propyl group, a 1-propyl group, a tert-pentyl group, a 2-pentyl group, a hexyl, Isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.
In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the above alkenyl group is 2 to 6. Specific examples thereof include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylethen-1-yl, 2-diphenylethen-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethen-1-yl, 2-bis (biphenyl-1-yl) ethen-1-yl, stilbenyl, and styryl.
In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, and according to one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 6. Specifically, there may be mentioned, but not limited to, 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.
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 having aromaticity. 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 a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aromatic group may be a naphthyl group, an anthryl group, a phenanthryl group, a triphenylene group, a pyrenyl group, a perylenyl group, a perylene group, a,
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 preferably the number of carbon atoms is 2 to 60. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, thienyl,
Azolyl radical、
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinyl
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl (phenanthroline), isoquinoyl
Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but is not limited thereto.
In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, arylamine group, and arylsilyl group is the same as the aryl group described above. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamino group is the same as the above-mentioned alkyl group. In the present specification, the heteroaryl group in the heteroarylamino group can be applied to the above description about the heteroaryl group. In the present specification, the alkenyl group in the aralkenyl group is the same as exemplified above for the alkenyl group. In the present specification, the arylene group is a 2-valent group, and the above description of the aryl group can be applied thereto. In the present specification, a heteroarylene group is a 2-valent group, and in addition to this, the above description about a heteroaryl group can be applied. In the present specification, the hydrocarbon ring is not a 1-valent group but is formed by combining 2 substituents, and in addition to this, the above description about the aryl group or the cycloalkyl group can be applied. In the present specification, the heterocyclic ring is not a 1-valent group but is formed by combining 2 substituents, and in addition to this, the above description on the heteroaryl group can be applied.
(Compound (I))
The present invention provides a compound represented by the above chemical formula 1.
The compound represented by the above chemical formula 1 is based on a compound of the following structure: with dibenzofuran as a core, and dibenzofuranyl, dibenzothienyl, or substituted or unsubstituted C is bonded to carbon number 6, carbon number 7, or both of the core6-60An aryl group; and pyridine, pyrimidine or triazine is bonded to the carbon number 1 of the core.
The organic light emitting device including the compound represented by the above chemical formula 1 as a constituent element of the organic layer exhibits higher heat resistance due to the kind of the above substituents and a synergistic effect by their binding sites with the above core, and may exhibit high efficiency and long life characteristics.
The following will describe the chemical formula 1 and the compound represented by the chemical formula in detail as follows.
Preferably, R1And R2Each independently is phenyl, biphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, phenanthryl, fluoranthenyl, or dibenzofuranyl.
Preferably, Ar1And Ar2Any of which is phenyl, biphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, phenanthryl, fluoranthenyl, triphenylenyl, dibenzofuranyl, benzonaphthofuranyl or benzonaphthothienyl, and the other is hydrogen.
Preferably, Ar1、Ar2、R1And R2At least one of which is naphthyl, phenylnaphthyl, naphthylphenyl, fluoranthenyl, benzonaphthofuranyl or benzonaphthothienyl.
For example, Ar1、Ar2、R1And R2At least two of which may be naphthyl, phenylnaphthyl, naphthylphenyl, fluoranthenyl, benzonaphthofuranyl or benzonaphthothienyl.
Preferably, X1Are all N.
Representative examples of the compound represented by the above chemical formula 1 are as follows:
the present invention also provides a method for producing the compound represented by the above chemical formula 1, as shown in the following reaction formula 1 or 2.
[ reaction formula 1]
[ reaction formula 2]
In the above reaction formulae 1 and 2, X' is a halogen, preferably bromine or chlorine. The other substituents are as defined above.
The above reaction formulas 1 and 2 are suzuki coupling reactions, preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups used for the suzuki coupling reactions may be modified according to techniques known in the art. The above-described manufacturing method can be further embodied in the manufacturing examples described later.
(organic light emitting device)
In addition, the present invention provides an organic light emitting device comprising the compound represented by the above chemical formula 1. As an example, the present invention provides an organic light emitting device, comprising: a first electrode; a second electrode provided to face the first electrode; and 1 or more organic layers disposed between the first electrode and the second electrode, wherein 1 or more of the organic layers include the compound represented by chemical formula 1.
The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have 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 a smaller number of organic layers may be included.
In addition, the organic layer may include a hole injection layer, a hole transport layer, or a layer simultaneously performing hole injection and transport, and the hole injection layer, the hole transport layer, or the layer simultaneously performing hole injection and transport includes the compound represented by the above chemical formula 1.
In addition, the organic layer may include a light emitting layer including the compound represented by the chemical formula 1.
The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have 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, as an organic layer, a hole injection layer and a hole transport layer between the first electrode and the light-emitting layer, and an electron transport layer and an electron injection layer between the light-emitting layer and the second electrode, in addition to the light-emitting layer. However, the structure of the organic light emitting device is not limited thereto, and a smaller number or a larger number of organic layers may be included.
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 the first electrode is an anode and the second electrode is a cathode, and the anode, 1 or more organic layers, and the cathode are sequentially stacked on the substrate. In addition, the organic light emitting device according to the present invention may be an inverted (inverted) type organic light emitting device in which the first electrode is a cathode and the second electrode is an anode, and the cathode, 1 or more organic layers, and the anode are sequentially stacked on the 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 composed of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be included in the above light emitting layer.
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 suppression 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 included 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 the above light emitting layer contains the compound according to the present invention and is manufactured as the above method.
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. In this case, the following production can be performed: the organic el display device is manufactured by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate by a PVD (physical Vapor Deposition) method such as a sputtering method or an electron beam evaporation method (e-beam evaporation) method to form an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the anode, and then depositing a substance that can be used as a cathode on the organic layer.
In addition to this method, an organic light-emitting device may be manufactured by depositing a cathode material, an organic layer, and an anode material on a substrate in this order (WO 2003/012890). However, the production method is not limited thereto.
In one example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.
The anode material is preferably a material having a large work function in order to smoothly inject holes 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-Al or SnO2A combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive compounds such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.
The cathode material is preferably a material having a small work function in order to easily inject 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 LiO2And a multilayer structure material such as Al, but not limited thereto.
The hole injection layer is a layer for injecting holes from the electrode, and the following compounds are preferable as the hole injection substance: a compound having an ability to transport holes, having an effect of injecting holes from an anode, having an excellent hole injection effect for a light-emitting layer or a light-emitting material, preventing excitons generated in the light-emitting layer from migrating to an electron injection layer or an electron injection material, and having an excellent thin film-forming ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive compounds.
The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport substance is a substance that can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer, and is preferably a substance having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive compounds, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.
The organic light emitting device according to an embodiment may further include an electron suppression layer on the hole transport layer. The electron-suppressing layer is a layer including: and a layer which is formed on the hole transport layer, is preferably provided in contact with the light-emitting layer, and serves to prevent excessive electron transfer by adjusting hole mobility, thereby increasing the probability of hole-electron combination, and thus improving the efficiency of the organic light-emitting device. The electron-suppressing layer contains an electron-suppressing substance, and examples of such an electron-suppressing substance include, but are not limited to, the compound represented by chemical formula 1, and arylamine-based organic substances.
The light emitting layer may include a host material and a dopant material. As the host material, the compound represented by the above chemical formula 1 may be used. In addition, as the host material, in addition to the compound represented by the above chemical formula 1, an aromatic fused ring derivative, a heterocyclic ring-containing compound, or the like may be further used. Specifically, the aromatic fused ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, and the like, and the heterocyclic ring-containing compound includes a carbazole derivative, a dibenzofuran derivative, a ladder furan compound, a pyrimidine derivative, and the like, but is not limited thereto.
Further, as the dopant material, there are an aromatic amine derivative, a styryl amine compound, a boron complex, a fluoranthene compound, a metal complex, and the like. Specifically, the aromatic amine derivative is an aromatic fused ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, or the like having an arylamino group,
And diindenopyrene, etc., the styrylamine compound is a substituted or unsubstituted arylamineThe compound substituted with at least 1 arylvinyl group is substituted or unsubstituted with 1 or 2 or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl and arylamino. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltrimethylamine, and styryltretramine. The metal complex includes, but is not limited to, iridium complexes and platinum complexes.
More specifically, as the dopant material, the following compounds can be used, but the dopant material is not limited thereto:
in addition, the organic light emitting device according to an embodiment may further include a hole blocking layer on the light emitting layer. The hole blocking layer is a layer including: and a layer which is formed on the light-emitting layer, preferably in contact with the light-emitting layer, and which prevents excessive hole migration by adjusting the electron mobility, thereby increasing the probability of hole-electron combination and improving the efficiency of the organic light-emitting device. The hole-blocking layer contains a hole-blocking substance, and examples of such hole-blocking substances include triazine-containing azine derivatives, triazole derivatives, and the like,
Examples of the compound to which an electron-withdrawing group is introduced include, but are not limited to, oxadiazole derivatives, phenanthroline derivatives, and phosphine oxide derivatives.
The electron injection and transport layer injects electrons from the electrode and receives the electronsA layer which functions as an electron transport layer and an electron injection layer while being transported to the light-emitting layer is formed on the light-emitting layer or the hole-blocking layer. Such an electron injecting and transporting substance is a substance that can favorably receive electrons from the cathode and transfer them to the light-emitting layer, and is suitable for a substance having a high mobility to electrons. As specific examples of the electron injecting and transporting substance, there are Al complexes of 8-hydroxyquinoline, Al complexes containing Alq3The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, a triazine derivative, etc., but are not limited thereto. Or with fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide,
Azole,
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complexes, nitrogen-containing five-membered ring derivatives, and the like are used together, but the present invention is not limited thereto.
The electron injection and transport layer may be formed as a separate layer such as an electron injection layer and an electron transport layer. In this case, an electron transport layer is formed on the light-emitting layer or the hole-blocking layer, and the electron injection and transport material described above can be used as the electron transport material contained in the electron transport layer. Further, an electron injection layer is formed on the electron transport layer, and LiF, NaCl, CsF, Li, or the like can be used as an electron injection substance contained in the electron injection layer2O, BaO, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide,
Azole,
Oxadiazoles, triazoles, imidazoles, benzimidazoles, perylenetetracarboxylic acids, fluorenylidenemethanes, anthrones, and the like, and derivatives thereof, metal complex compounds, and nitrogen-containing pentanesA cyclic ring derivative, and the like.
In addition, the compound according to the present invention may be included in an organic solar cell or an organic transistor, in addition to the organic light emitting device.
The manufacture 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 provided to illustrate the present invention, and the scope of the present invention is not limited thereto.
Synthesis example 1
Under a nitrogen atmosphere, formula A (15g, 60.9mmol) and Trz1(24g, 60.9mmol) were added to 300ml THF, stirred and refluxed. Then, potassium carbonate (16.8g, 121.7mmol) was dissolved in 50ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphine) palladium (0) (bis (0) (0.3g, 0.6mmol) was charged. After 12 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.8g of substance (sub) A-1. (yield 64%, MS: [ M + H ]]+＝560)
Substance A-1(15g, 26.8mmol) and substance 1(3.6g, 29.5mmol) were added to 300ml of THF under nitrogen, stirred and refluxed. Then, potassium carbonate (11.1g, 80.3mmol) was dissolved in 33ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.1g, 0.3mmol) was charged. After 8 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer was separated from the aqueous layer, followed by distillation of the organic layer. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.1g of compound 1. (yield 69%, MS: [ M + H ]]+＝602)
Synthesis example 2
Under a nitrogen atmosphere, formula A (15g, 60.9mmol) and Trz2(27g, 60.9mmol) were added to 300ml THF, stirred and refluxed. Then, potassium carbonate (16.8g, 121.7mmol) was dissolved in 50ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.6mmol) was charged. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26.3g of substance A-2. (yield 71%, MS: [ M + H ]]+＝610)
Substance A-2(15g, 24.6mmol) and substance 1(3.3g, 27mmol) were added to 300ml of THF under nitrogen, stirred and refluxed. Then, potassium carbonate (10.2g, 73.8mmol) was dissolved in 31ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.1g, 0.2mmol) was charged. After 10 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.6g of compound 2. (yield 79%, MS: [ M + H ]]+＝652)
Synthesis example 3
Under nitrogen, formula A (15g, 60.9mmol) and Trz3(23.9g, 60.9mmol) were added to 300ml THF, stirred and refluxed. Then, potassium carbonate (16.8g, 121.7mmol) was dissolved in 50ml of water and charged, and after sufficiently stirring, bis (methyl methacrylate) was charged(Tri-tert-butylphosphine) palladium (0) (0.3g, 0.6 mmol). After 10 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26.4g of substance A-3. (yield 78%, MS: [ M + H ]]+＝558)
Substance A-3(15g, 26.9mmol) and substance 1(3.6g, 29.6mmol) were added to 300ml of THF under nitrogen, stirred and refluxed. Then, potassium carbonate (11.1g, 80.6mmol) was dissolved in 33ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.1g, 0.3mmol) was charged. After 10 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.7g of compound 3. (yield 79%, MS: [ M + H ]]+＝600)
Synthesis example 4
Under nitrogen, formula A (15g, 60.9mmol) and Trz4(23.9g, 60.9mmol) were added to 300ml THF, stirred and refluxed. Then, potassium carbonate (16.8g, 121.7mmol) was dissolved in 50ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.6mmol) was charged. After 11 hours of the reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 24.8g of substance A-4. (yield 73%, MS: [ M + H ]]+＝558)
Under nitrogen, substance A-4(15g, 26.9mmol) and substance 1(3.6g, 29.6mmol)mmol) was added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (11.1g, 80.6mmol) was dissolved in 33ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.1g, 0.3mmol) was charged. After 12 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.6g of compound 4. (yield 72%, MS: [ M + H ]]+＝600)
Synthesis example 5
Under a nitrogen atmosphere, formula A (15g, 60.9mmol) and Trz5(27g, 60.9mmol) were added to 300ml THF, stirred and refluxed. Then, potassium carbonate (16.8g, 121.7mmol) was dissolved in 50ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.6mmol) was charged. After 10 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 28.9g of substance A-5. (yield 78%, MS: [ M + H ]]+＝610)
Under nitrogen, substance A-5(15g, 24.6mmol) and substance 1(3.3g, 27mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (10.2g, 73.8mmol) was dissolved in 31ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.1g, 0.2mmol) was charged. After 11 hours of the reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.2g of compound 5. (yield 76%, MS: [ M + H ]]+＝652)
Synthesis example 6
Under nitrogen, formula A (15g, 60.9mmol) and Trz6(21.8g, 60.9mmol) were added to 300ml THF, stirred and refluxed. Then, potassium carbonate (16.8g, 121.7mmol) was dissolved in 50ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.6mmol) was charged. After 10 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.3g of substance A-6. (yield 67%, MS: [ M + H ]]+＝524)
Under nitrogen, substance A-6(15g, 28.6mmol) and substance 2(5.4g, 31.5mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (11.9g, 85.9mmol) was dissolved in 36ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.1g, 0.3mmol) was charged. After 8 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer was separated from the aqueous layer, followed by distillation of the organic layer. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.9g of compound 6. (yield 73%, MS: [ M + H ]]+＝616)
Synthesis example 7
Under nitrogen, formula A (15g, 60.9mmol) and Trz7(19.3g, 60.9mmol) were added to 300ml THF, stirred and refluxed. Then, potassium carbonate (16.8g, 121.7mmol) was dissolved in 50ml of water and chargedAfter stirring sufficiently, bis (tri-tert-butylphosphine) palladium (0) (0.3g, 0.6mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.7g of substance A-7. (yield 67%, MS: [ M + H ]]+＝484)
Substance A-7(15g, 31mmol) and substance 2(5.9g, 34.1mmol) were added to 300ml of THF under nitrogen, stirred and refluxed. Then, potassium carbonate (12.9g, 93mmol) was dissolved in 39ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was charged. After 12 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.1g of compound 7. (yield 62%, MS: [ M + H ]]+＝576)
Synthesis example 8
Under nitrogen, formula A (15g, 60.9mmol) and Trz8(21.8g, 60.9mmol) were added to 300ml THF, stirred and refluxed. Then, potassium carbonate (16.8g, 121.7mmol) was dissolved in 50ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.6mmol) was charged. After 10 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.9g of substance A-8. (yield 72%, MS: [ M + H ]]+＝524)
Substance A-8(15g, 28) was added under nitrogen.6mmol) and substance 2(5.4g, 31.5mmol) are added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (11.9g, 85.9mmol) was dissolved in 36ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.1g, 0.3mmol) was charged. After 12 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.7g of compound 8. (yield 72%, MS: [ M + H ]]+＝616)
Synthesis example 9
Under nitrogen, formula A (15g, 60.9mmol) and Trz9(20.9g, 60.9mmol) were added to 300ml THF, stirred and refluxed. Then, potassium carbonate (16.8g, 121.7mmol) was dissolved in 50ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.6mmol) was charged. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.2g of substance A-9. (yield 62%, MS: [ M + H ]]+＝510)
Substance A-9(15g, 29.9mmol) and substance 3(8.2g, 32.9mmol) were added to 300ml of THF under nitrogen, stirred and refluxed. Then, potassium carbonate (12.4g, 89.8mmol) was dissolved in 37ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was charged. After 10 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. Purifying the concentrated compound by silica gel column chromatographyThus, 12.4g of Compound 9 was produced. (yield 61%, MS: [ M + H ]]+＝678)
Synthesis example 10
Under nitrogen, formula A (15g, 60.9mmol) and Trz10(16.3g, 60.9mmol) were added to 300ml THF, stirred and refluxed. Then, potassium carbonate (16.8g, 121.7mmol) was dissolved in 50ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.6mmol) was charged. After 11 hours of the reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17.4g of substance A-10. (yield 66%, MS: [ M + H ]]+＝435)
Under nitrogen, substance A-10(15g, 34.6mmol) and substance 4(9.4g, 38mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (14.3g, 103.7mmol) was dissolved in 43ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was charged. After 8 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer was separated from the aqueous layer, followed by distillation of the organic layer. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15g of compound 10. (yield 72%, MS: [ M + H ]]+＝602)
Synthesis example 11
Substance A-7(15g, 31mmol) and substance 5(9.3g, 34.1mmol) were added to 300ml of THF under nitrogen, stirred and refluxed. Then, potassium carbonate (12.9g, 93mmol)Dissolved in 39ml of water, and after sufficiently stirring, bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.3mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.3g of compound 11. (yield 78%, MS: [ M + H ]]+＝676)
Synthesis example 12
Under nitrogen, substance A-10(15g, 34.6mmol) and substance 6(10g, 38mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (14.3g, 103.7mmol) was dissolved in 43ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was charged. After 10 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.6g of compound 12. (yield 78%, MS: [ M + H ]]+＝616)
Synthesis example 13
Under nitrogen, substance A-10(15g, 34.6mmol) and substance 7(10.6g, 38mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (14.3g, 103.7mmol) was dissolved in 43ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was charged. After 11 hours of the reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. Dissolving in chloroform again, washing with water for 2 times, and separating organic layerAnhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17g of compound 13. (yield 78%, MS: [ M + H ]]+＝632)
Synthesis example 14
Under nitrogen, substance A-10(15g, 34.6mmol) and substance 8(10g, 38mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (14.3g, 103.7mmol) was dissolved in 43ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was charged. After 12 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16g of compound 14. (yield 75%, MS: [ M + H ]]+＝616)
Synthesis example 15
Under nitrogen, substance A-10(15g, 34.6mmol) and substance 9(10g, 38mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (14.3g, 103.7mmol) was dissolved in 43ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was charged. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.6g of compound 15. (yield 78%, MS: [ M + H ]]+＝616)
Synthesis example 16
Substance A-10(15g, 34.6mmol) and substance 10(10g, 38mmol) were added to 300ml of THF under nitrogen, stirred and refluxed. Then, potassium carbonate (14.3g, 103.7mmol) was dissolved in 43ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was charged. After 12 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.8g of compound 16. (yield 79%, MS: [ M + H ]]+＝616)
Synthesis example 17
Under nitrogen, substance A-10(15g, 34.6mmol) and substance 11(10.6g, 38mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (14.3g, 103.7mmol) was dissolved in 43ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was charged. After 11 hours of the reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.1g of compound 17. (yield 69%, MS: [ M + H ]]+＝632)
Synthesis example 18
Under nitrogen atmosphere, substance A-10(15g, 34.6mmol) andmaterial 12(10.6g, 38mmol) was added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (14.3g, 103.7mmol) was dissolved in 43ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was charged. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.9g of compound 18. (yield 73%, MS: [ M + H ]]+＝632)
Synthesis example 19
Under nitrogen, formula B (15g, 60.9mmol) and Trz11(24.8g, 60.9mmol) were added to 300ml THF, stirred and refluxed. Then, potassium carbonate (16.8g, 121.7mmol) was dissolved in 50ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.6mmol) was charged. After 11 hours of the reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 25.5g of substance B-1. (yield 73%, MS: [ M + H ]]+＝574)
Under nitrogen, substance B-1(15g, 26.1mmol) and substance 1(3.5g, 28.7mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (10.8g, 78.4mmol) was dissolved in 33ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.1g, 0.3mmol) was charged. After 11 hours of the reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. Purifying the concentrated compound by silica gel column chromatography to obtain10.1g of Compound 19 was produced. (yield 63%, MS: [ M + H ]]+＝616)
Synthesis example 20
Under nitrogen, formula B (15g, 60.9mmol) and Trz12(29.5g, 60.9mmol) were added to 300ml THF, stirred and refluxed. Then, potassium carbonate (16.8g, 121.7mmol) was dissolved in 50ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.6mmol) was charged. After 11 hours of the reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 29.6g of substance B-2. (yield 75%, MS: [ M + H ]]+＝650)
Under nitrogen, substance B-2(15g, 23.1mmol) and substance 1(3.1g, 25.4mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (9.6g, 69.2mmol) was dissolved in 29ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.1g, 0.2mmol) was charged. After 8 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer was separated from the aqueous layer, followed by distillation of the organic layer. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.6g of compound 20. (yield 73%, MS: [ M + H ]]+＝692)
Synthesis example 21
Under nitrogen, formula B (15g, 60.9mmol) and Trz4(23.9g, 60.9mmol) were added to 300ml THF, stirred and refluxed. Then, potassium carbonate (16.8g, 121.7mmol) was dissolvedThe solution was dissolved in 50ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphine) palladium (0) (0.3g, 0.6mmol) was charged. After 11 hours of the reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26.8g of substance B-3. (yield 79%, MS: [ M + H ]]+＝558)
Under nitrogen, substance B-3(15g, 26.9mmol) and substance 1(3.6g, 29.6mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (11.1g, 80.6mmol) was dissolved in 33ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.1g, 0.3mmol) was charged. After 10 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 9.7g of compound 21. (yield 60%, MS: [ M + H ]]+＝600)
Synthesis example 22
Under nitrogen, formula B (15g, 60.9mmol) and Trz2(19.3g, 60.9mmol) were added to 300ml THF, stirred and refluxed. Then, potassium carbonate (16.8g, 121.7mmol) was dissolved in 50ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.6mmol) was charged. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.2g of substance B-4. (yield 62%, MS: [ M + H ]]+＝484)
Under nitrogenSubstance B-4(15g, 24.6mmol) and substance 1(3.3g, 27mmol) were added to 300ml of THF under an atmosphere, stirred and refluxed. Then, potassium carbonate (10.2g, 73.8mmol) was dissolved in 31ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.1g, 0.2mmol) was charged. After 12 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.8g of compound 22. (yield 80%, MS: [ M + H ]]+＝652)
Synthesis example 23
Under nitrogen, formula B (15g, 60.9mmol) and Trz7(21.8g, 60.9mmol) were added to 300ml THF, stirred and refluxed. Then, potassium carbonate (16.8g, 121.7mmol) was dissolved in 50ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.6mmol) was charged. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.7g of substance B-5. (yield 62%, MS: [ M + H ]]+＝524)
Under nitrogen, substance B-5(15g, 31mmol) and substance 2(6.1g, 34.1mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (12.9g, 93mmol) was dissolved in 39ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was charged. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound is applied to silica gelPurification was performed by column chromatography, whereby 14.3g of compound 23 was produced. (yield 80%, MS: [ M + H ]]+＝576)
Synthesis example 24
Under nitrogen, formula B (15g, 60.9mmol) and Trz8(21.8g, 60.9mmol) were added to 300ml THF, stirred and refluxed. Then, potassium carbonate (16.8g, 121.7mmol) was dissolved in 50ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.6mmol) was charged. After 11 hours of the reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.7g of substance B-6. (yield 68%, MS: [ M + H ]]+＝524)
Under nitrogen, substance B-6(15g, 28.6mmol) and substance 2(5.6g, 31.5mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (11.9g, 85.9mmol) was dissolved in 36ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.1g, 0.3mmol) was charged. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.2g of compound 24. (yield 75%, MS: [ M + H ]]+＝616)
Synthesis example 25
Under nitrogen, formula B (15g, 60.9mmol) and Trz13(21.8g, 60.9mmol) were added to 300ml THF, stirred and refluxed. Then, the user can use the device to perform the operation,potassium carbonate (16.8g, 121.7mmol) was dissolved in 50ml of water and charged, and after stirring sufficiently, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.6mmol) was charged. After 12 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.1g of substance B-7. (yield 63%, MS: [ M + H ]]+＝524)
Under nitrogen, substance B-7(15g, 28.6mmol) and substance 2(5.6g, 31.5mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (11.9g, 85.9mmol) was dissolved in 36ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.1g, 0.3mmol) was charged. After 8 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer was separated from the aqueous layer, followed by distillation of the organic layer. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.6g of compound 25. (yield 66%, MS: [ M + H ]]+＝616)
Synthesis example 26
Under nitrogen, formula B (15g, 60.9mmol) and Trz9(20.9g, 60.9mmol) were added to 300ml THF, stirred and refluxed. Then, potassium carbonate (16.8g, 121.7mmol) was dissolved in 50ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.6mmol) was charged. After 8 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer was separated from the aqueous layer, followed by distillation of the organic layer. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.2g of substance B-8. (yield 62%, MS: [ M + H ]]+＝510)
Under nitrogen, substance B-8(15g, 29.4mmol) and substance 2(5.8g, 32.4mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (12.2g, 88.2mmol) was dissolved in 37ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was charged. After 12 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.6g of compound 26. (yield 71%, MS: [ M + H ]]+＝602)
Synthesis example 27
Under nitrogen, substance B-5(15g, 31mmol) and substance 13(6.8g, 34.1mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (12.9g, 93mmol) was dissolved in 39ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was charged. After 12 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.9g of compound 27. (yield 64%, MS: [ M + H ]]+＝602)
Synthesis example 28
Under nitrogen, formula B (15g, 60.9mmol) and Trz10(16.3g, 60.9mmol) were added to 300ml THF, stirred and refluxed. Then, potassium carbonate (16.8g, 121.7mmol) was dissolved in 50ml of water and charged, and after sufficiently stirring, bis (tri-t-butylphosphine) was charged) Palladium (0) (0.3g, 0.6 mmol). After 11 hours of the reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.3g of substance B-9. (yield 77%, MS: [ M + H ]]+＝434)
Under nitrogen, substance B-9(15g, 34.6mmol) and substance 14(9.4g, 38mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (14.3g, 103.7mmol) was dissolved in 43ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was charged. After 12 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.5g of compound 28. (yield 75%, MS: [ M + H ]]+＝600)
Synthesis example 29
Under nitrogen, substance B-9(15g, 34.6mmol) and substance 15(9.4g, 38mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (14.3g, 103.7mmol) was dissolved in 43ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was charged. After 12 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.3g of compound 29. (yield 74%, MS: [ M + H ]]+＝600)
Synthesis example 30
Under nitrogen, substance B-9(15g, 34.6mmol) and substance 16(9.4g, 38mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (14.3g, 103.7mmol) was dissolved in 43ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was charged. After 12 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.4g of compound 30. (yield 60%, MS: [ M + H ]]+＝600)
Synthesis example 31
Under nitrogen, substance B-5(15g, 31mmol) and substance 17(7.2g, 34.1mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (12.9g, 93mmol) was dissolved in 39ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was charged. After 11 hours of the reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.8g of compound 31. (yield 62%, MS: [ M + H ]]+＝616)
Synthesis example 32
Under nitrogen, substance B-9(15g, 34.6mmol) and substance 10(8.1g, 38mmol) were added to 300ml of THF, stirred andand (4) refluxing. Then, potassium carbonate (14.3g, 103.7mmol) was dissolved in 43ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was charged. After 12 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.6g of compound 32. (yield 78%, MS: [ M + H ]]+＝616)
Synthesis example 33
Under nitrogen, substance B-9(15g, 34.6mmol) and substance 6(8.1g, 38mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (14.3g, 103.7mmol) was dissolved in 43ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was charged. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16g of compound 33. (yield 75%, MS: [ M + H ]]+＝616)
Synthesis example 34
Under nitrogen, substance B-9(15g, 34.6mmol) and substance 18(8.1g, 38mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (14.3g, 103.7mmol) was dissolved in 43ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was charged. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. Dissolving it in water againChloroform, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.6g of compound 34. (yield 78%, MS: [ M + H ]]+＝616)
Synthesis example 35
Under nitrogen, substance B-9(15g, 34.6mmol) and substance 19(8.1g, 38mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (14.3g, 103.7mmol) was dissolved in 43ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was charged. After 8 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer was separated from the aqueous layer, followed by distillation of the organic layer. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.5g of compound 35. (yield 68%, MS: [ M + H ]]+＝616)
Synthesis example 36
Under nitrogen, substance B-9(15g, 34.6mmol) and substance 20(8.1g, 38mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (14.3g, 103.7mmol) was dissolved in 43ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was charged. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.4g of compound 36. (yield 77%, MS: [ M + H ]]+＝616)
Synthesis example 37
Under nitrogen, substance B-9(15g, 34.6mmol) and substance 21(10.6g, 38mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (14.3g, 103.7mmol) was dissolved in 43ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was charged. After 12 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.1g of compound 37. (yield 60%, MS: [ M + H ]]+＝632)
Synthesis example 38
Under nitrogen, substance B-9(15g, 34.6mmol) and substance 22(10.6g, 38mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (14.3g, 103.7mmol) was dissolved in 43ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was charged. After 10 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17.5g of compound 38. (yield 80%, MS: [ M + H ]]+＝632)
Synthesis example 39
Under nitrogen, substance B-9(15g, 34.6mmol) and substance 23(10.6g, 38mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (14.3g, 103.7mmol) was dissolved in 43ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was charged. After 11 hours of the reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.6g of compound 39. (yield 67%, MS: [ M + H ]]+＝632)
Synthesis example 40
Under nitrogen, substance B-9(15g, 34.6mmol) and substance 24(10.6g, 38mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (14.3g, 103.7mmol) was dissolved in 43ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was charged. After 12 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.1g of compound 40. (yield 60%, MS: [ M + H ]]+＝632)
Example 1
Indium Tin Oxide (ITO) and a process for producing the same
The glass substrate coated with a thin film of (3) is put in distilled water in which a detergent is dissolved, and washed by ultrasonic waves. In this case, the detergent was prepared by Fisher Co, and the distilled water was distilled by twice filtration using a Filter (Filter) manufactured by Millipore CoAnd (3) water. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone, or methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.
On the ITO transparent electrode thus prepared, as a hole injection layer, the following HI-1 compound was added
And the following a-1 compound was p-doped (p-doping) at a concentration of 1.5%. Vacuum evaporation of the following HT-1 compound was performed on the hole injection layer to form a film having a thickness
The hole transport layer of (1). Then, on the hole transport layer, the film thickness
The following EB-1 compound was vacuum-deposited to form an electron-inhibiting layer. Then, on the EB-1 vapor deposited film, compound 1 and the following Dp-7 compound were formed by vacuum vapor deposition at a weight ratio of 98:2
A thick red light emitting layer. On the light-emitting layer, the thickness of the film
A hole-blocking layer was formed by vacuum vapor deposition of the following HB-1 compound. Next, 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 to form a hole blocking layer
The thickness of (a) forms an electron injection and transport layer. On the above electron injection and transport layer, lithium fluoride (LiF) is sequentially added to
Thickness of aluminum and
the thickness of (3) is evaporated to form a cathode.
In the above process, the evaporation speed of the organic material is maintained
Lithium fluoride maintenance of cathode
Deposition rate of (3), aluminum maintenance
The vapor deposition rate of (2) is maintained at a vacuum degree of 2X 10 during vapor deposition-7～5×10-6And supporting to thereby fabricate an organic light emitting device.
Examples 2 to 40
An organic light-emitting device was produced in the same manner as in example 1 above, except that the compound described in table 1 below was used instead of compound 1 in the organic light-emitting device of example 1.
Comparative examples 1 to 16
An organic light-emitting device was produced in the same manner as in example 1 above, except that compounds C-1 to C-16 described in table 1 below were used instead of compound 1 in the organic light-emitting device of example 1. Compounds C-1 to C-16 herein are shown below:
examples of the experiments
When a current was applied to the organic light emitting devices manufactured in the above-described examples 1 to 40 and comparative examples 1 to 16, (10 mA/cm) was measured2) The results of voltage and efficiency are shown in table 1 below. The lifetime T95 refers to the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.
[ Table 1]
When a current was applied to the organic light emitting devices fabricated by examples 1 to 40 and comparative examples 1 to 16, the results of table 1 above were obtained.
The red organic light-emitting device of example 1 used a substance that has been widely used conventionally, and had a structure in which the compound [ EB-1] was used as an electron blocking layer and the compound 1/Dp-7 was used as a red light-emitting layer. In addition, examples 2 to 40 used compounds 2 to 40 instead of compound 1, and comparative examples 1 to 16 used compounds C-1 to C-16 instead of compound 1, thereby manufacturing organic light emitting devices.
As seen from the results of table 1, when the compound of the present invention is used in the light-emitting layer, the driving voltage is significantly reduced compared to the comparative example substance, and the efficiency is also significantly improved, so that it is understood that energy transfer from the host to the red dopant is smoothly achieved. Further, it is found that the life characteristics can be greatly improved while maintaining high efficiency. It is judged that this is because the stability of the compound of the present invention with respect to electrons and holes is high as compared with the compound of comparative example.
As a result, it was confirmed that when the compound of the present invention was used as a host of a red light emitting layer, driving voltage, light emitting efficiency and life characteristics of an organic light emitting device could be improved.
[ description of symbols ]
1: substrate 2: anode
3: light-emitting layer 4: cathode electrode
5: hole injection layer 6: hole transport layer
7: electron suppression layer 8: hole blocking layer
9: an electron injection and transport layer.
Claims (8)
1. A compound represented by the following chemical formula 1:
chemical formula 1
In the chemical formula 1, the first and second organic solvents,
R1and R2Each independently is substituted or unsubstituted C6-60Aryl, dibenzofuranyl or dibenzothiophenyl,
X1each independently is N or CH, and the X1At least one of which is N,
Ar1and Ar2Each independently hydrogen, deuterium, unsubstituted C6-60Aryl group, or a substituent represented by the following chemical formula 2,
chemical formula 2
In the chemical formula 2,
X2is O or S, and is a compound of,
R3to R10Any one of which is bound to the chemical formula 1, and R which is not bound to the chemical formula 13To R10Each independently hydrogen or deuterium, or capable of bonding to an adjacent group to form an aromatic ring,
Ar1、Ar2、R1and R2At least one of which is naphthyl, phenylnaphthyl, naphthylphenyl, fluoranthenyl, benzonaphthofuranyl or benzonaphthothienyl.
2. The compound of claim 1, wherein R1And R2Each independently is phenyl, biphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, phenanthryl, fluoranthenyl, or dibenzofuranyl.
3. The compound of claim 1, wherein Ar1And Ar2Any of which is phenyl, biphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, phenanthryl, fluoranthenyl, triphenylenyl, dibenzofuranyl, benzonaphthofuranyl or benzonaphthothienyl, and the other is hydrogen.
4. The compound of claim 1, wherein X1Are all N.
5. The compound of claim 1, wherein Ar1、Ar2、R1And R2At least two of which are naphthyl, phenylnaphthyl, naphthylphenyl, fluoranthenyl, benzonaphthofuranyl or benzonaphthothienyl.
6. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is any one selected from the group consisting of:
7. an organic light emitting device, comprising: a first electrode; a second electrode provided to face the first electrode; and 1 or more organic layers disposed between the first electrode and the second electrode, 1 or more of the organic layers comprising the compound of any one of claims 1 to 6.
8. The organic light-emitting device according to claim 7, wherein the organic layer containing the compound is a light-emitting layer.
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| WO2020116822A1 (en) * | 2018-12-07 | 2020-06-11 | 덕산네오룩스 주식회사 | Compound for organic electric device, organic electric device using same, and electronic apparatus thereof |
| WO2020122460A1 (en) * | 2018-12-12 | 2020-06-18 | 삼성에스디아이 주식회사 | Compound for organic optoelectronic diode, organic optoelectronic diode, and display device |
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| WO2020116822A1 (en) * | 2018-12-07 | 2020-06-11 | 덕산네오룩스 주식회사 | Compound for organic electric device, organic electric device using same, and electronic apparatus thereof |
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| CN114702482B (en) * | 2022-05-09 | 2024-05-28 | 阜阳欣奕华材料科技有限公司 | Triazine compound, intermediate, organic electroluminescent device and display device |
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