CN115991699A - Naphthalene bridging double-suction fragment compound - Google Patents
Naphthalene bridging double-suction fragment compound Download PDFInfo
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- CN115991699A CN115991699A CN202111203040.2A CN202111203040A CN115991699A CN 115991699 A CN115991699 A CN 115991699A CN 202111203040 A CN202111203040 A CN 202111203040A CN 115991699 A CN115991699 A CN 115991699A
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- water
- 1mol
- aryl
- substituted
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 43
- 125000001624 naphthyl group Chemical group 0.000 title claims abstract description 16
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 239000012634 fragment Substances 0.000 title abstract description 7
- 239000000463 material Substances 0.000 claims abstract description 76
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 62
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- -1 pyridopyrazinyl Chemical group 0.000 claims description 17
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 11
- 239000004305 biphenyl Substances 0.000 claims description 11
- 235000010290 biphenyl Nutrition 0.000 claims description 11
- 125000000732 arylene group Chemical group 0.000 claims description 10
- 239000004973 liquid crystal related substance Substances 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000005549 heteroarylene group Chemical group 0.000 claims description 8
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 6
- 125000005561 phenanthryl group Chemical group 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 6
- 125000004306 triazinyl group Chemical group 0.000 claims description 6
- 125000005580 triphenylene group Chemical group 0.000 claims description 6
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- 125000001769 aryl amino group Chemical group 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 229910052805 deuterium Inorganic materials 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000004982 aromatic amines Chemical class 0.000 claims description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 2
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical compound N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 claims description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 2
- 125000005556 thienylene group Chemical group 0.000 claims description 2
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 2
- 239000007787 solid Substances 0.000 abstract description 147
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 162
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 134
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 126
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 116
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 84
- 239000012074 organic phase Substances 0.000 description 56
- 239000000843 powder Substances 0.000 description 56
- 229910000027 potassium carbonate Inorganic materials 0.000 description 42
- 239000000376 reactant Substances 0.000 description 38
- 238000002347 injection Methods 0.000 description 30
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 30
- 230000015572 biosynthetic process Effects 0.000 description 25
- 238000003786 synthesis reaction Methods 0.000 description 25
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 24
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 24
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 24
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- IBGUDZMIAZLJNY-UHFFFAOYSA-N 1,4-dibromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=C(Br)C2=C1 IBGUDZMIAZLJNY-UHFFFAOYSA-N 0.000 description 13
- 239000002019 doping agent Substances 0.000 description 13
- 229910052763 palladium Inorganic materials 0.000 description 13
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
- 235000011056 potassium acetate Nutrition 0.000 description 12
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- USVZFSNDGFNNJT-UHFFFAOYSA-N cyclopenta-1,4-dien-1-yl(diphenyl)phosphane (2,3-dichlorocyclopenta-1,4-dien-1-yl)-diphenylphosphane iron(2+) Chemical compound [Fe++].c1cc[c-](c1)P(c1ccccc1)c1ccccc1.Clc1c(cc[c-]1Cl)P(c1ccccc1)c1ccccc1 USVZFSNDGFNNJT-UHFFFAOYSA-N 0.000 description 9
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- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 8
- BZUUVQCSPHPUQA-UHFFFAOYSA-N 2-bromo-5-chloropyridine Chemical compound ClC1=CC=C(Br)N=C1 BZUUVQCSPHPUQA-UHFFFAOYSA-N 0.000 description 6
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- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Abstract
The present application provides a compound of formula (I) which can be used in electron transport materials. The compound has a parent structure of naphthalene bridging double-absorption fragments, has high bond energy among atoms, good thermal stability, is favorable for solid accumulation among molecules, has strong electron transition capability, and can effectively reduce the driving voltage of an organic electroluminescent device, improve the luminous efficiency and prolong the service life when being used as an electron transport material. The application also provides an organic electroluminescent device and a display device comprising the compound of the general formula (I).
Description
Technical Field
The present disclosure relates to the field of organic light emitting display technology, and in particular, to an electron transport material and an organic electroluminescent device including the electron transport material.
Background
Electroluminescence (EL) refers to a phenomenon in which a light emitting material emits light when excited by current and voltage under the action of an electric field, and is a light emitting process in which electric energy is directly converted into light energy. The organic electroluminescent display (OLED) has the advantages of self-luminescence, low voltage DC drive, full solidification, wide viewing angle, light weight, simple composition and process, etc., compared with the liquid crystal display, the organic electroluminescent display does not need a backlight source, has large viewing angle and low power, the response speed can reach 1000 times of the liquid crystal display, and the manufacturing cost is lower than that of the liquid crystal display with the same resolution. Therefore, the organic electroluminescent device has very wide application prospect.
With the continuous advancement of OLED technology in the two fields of illumination and display, people pay more attention to the research on efficient organic materials affecting the performance of OLED devices, and an organic electroluminescent device with good efficiency and long service life is usually the result of the optimized collocation of device structures and various organic materials, which provides great opportunities and challenges for chemists to design and develop functional materials with various structures.
Organic electroluminescent materials have many advantages over inorganic luminescent materials, such as: the processing performance is good, film can be formed on any substrate by a vapor deposition or spin coating method, and flexible display and large-area display can be realized; the optical property, the electrical property, the stability and the like of the material can be adjusted by changing the structure of the molecule, and the material has a large space to select. In the most common OLED device structures, the following classes of organic materials are typically included: a hole injection material, a hole transport material, an electron transport material, a light emitting material (dye or doped guest material) of each color, a corresponding host material, and the like. Currently, an electron transport material is an important functional material, which has a direct effect on the mobility of electrons and ultimately affects the luminous efficiency of an OLED. However, the electron transfer rate achieved by the electron transport materials currently applied to the OLED is low, and the energy level matching with the adjacent layers is poor, which severely restricts the light emitting efficiency of the OLED and the display function of the OLED display device. The development of electron transport materials with higher mobility is of great importance for improving device performance.
Disclosure of Invention
The embodiment of the application aims to provide an electron transport material so as to improve the working efficiency and prolong the service life of an organic electroluminescent device.
A first aspect of the present application provides a compound of formula (I):
wherein, the liquid crystal display device comprises a liquid crystal display device,
Ar 1 selected from C 6 -C 30 Aryl or C of (2) 5 -C 30 The hydrogen atoms on the aryl and heteroaryl groups each independently may be substituted with Ra;
Ar 2 selected from C 10 -C 30 Aryl or C of (2) 5 -C 30 The hydrogen atoms on the aryl and heteroaryl groups each independently may be substituted with Ra;
X 1 -X 3 selected from CH or N, and at least two selected from N;
Y 1 -Y 5 selected from CR or N, and at least one selected from N, R is selected from hydrogen、C 6 -C 30 Aryl or C of (2) 3 -C 30 Adjacent R may form a ring, and the hydrogen atoms on the aryl and heteroaryl groups may each independently be substituted with Ra;
L 1 and L 2 Each independently selected from chemical bonds, C 6 -C 30 Arylene or C of (2) 3 -C 30 The hydrogen atoms on the arylene and heteroarylene groups each independently may be substituted with Ra;
the heteroatoms on the heteroaryl or the heteroarylene are each independently selected from O, S or N;
the substituents Ra of each group are each independently selected from deuterium, halogen, nitro, cyano, C 1 -C 4 Alkyl, phenyl, biphenyl, terphenyl or naphthyl.
A second aspect of the present application provides an electron transport material comprising at least one of the compounds provided herein.
A third aspect of the present application provides an organic electroluminescent device comprising at least one of the electron transport materials provided herein.
A fourth aspect of the present application provides a display device comprising the organic electroluminescent device provided herein.
The compound provided by the application has a parent structure of naphthalene bridging double-absorption fragments, has high bond energy among atoms, good thermal stability, is favorable for solid stacking among molecules, and has strong electron transition capability. When the organic electroluminescent material is used as an electron transport material, the organic electroluminescent material has a matched energy level with adjacent layers, is favorable for electron injection and migration, can effectively reduce driving voltage, has higher electron migration rate, and can realize good luminous efficiency in an organic electroluminescent device. When the organic electroluminescent device containing the compound is applied as an electron transport material, the driving voltage of the organic electroluminescent device can be effectively reduced, the luminous efficiency of the organic electroluminescent device can be improved, and the service life of the organic electroluminescent device can be prolonged. The display device provided by the application has excellent display effect.
Of course, not all of the above-described advantages need be achieved simultaneously in practicing any one of the products or methods of the present application.
Drawings
In order to more clearly illustrate the embodiments of the present application or the technical solutions in the prior art, the following description will briefly introduce the drawings that are required to be used in the embodiments or the description of the prior art, it is obvious that the drawings in the following description are only one embodiment of the present application, and other embodiments may be obtained according to these drawings to those skilled in the art.
Fig. 1 is a schematic structural view of a typical organic electroluminescent device.
Detailed Description
The following description of the embodiments of the present application will be made clearly and fully with reference to the accompanying drawings, in which it is evident that the embodiments described are only some, but not all, of the embodiments of the present application. All other embodiments obtained by those skilled in the art based on the embodiments herein fall within the scope of the protection of the present application.
A first aspect of the present application provides a compound of formula (I):
wherein, the liquid crystal display device comprises a liquid crystal display device,
Ar 1 selected from C 6 -C 30 Aryl or C of (2) 5 -C 30 The hydrogen atoms on the aryl and heteroaryl groups each independently may be substituted with Ra;
Ar 2 Selected from C 10 -C 30 Aryl or C of (2) 5 -C 30 The hydrogen atoms on the aryl and heteroaryl groups each independently may be substituted with Ra;
X 1 -X 3 selected from CH or N, and at least two selected from N;
Y 1 -Y 5 selected from CR or N, and at least one selected from N, R is selected from hydrogen, C 6 -C 30 Aryl or C of (2) 3 -C 30 Adjacent R may form a ring, and the hydrogen atoms on the aryl and heteroaryl groups may each independently be substituted with Ra;
L 1 and L 2 Each independently selected from chemical bonds, C 6 -C 30 Arylene or C of (2) 3 -C 30 The hydrogen atoms on the arylene and heteroarylene groups each independently may be substituted with Ra;
the heteroatoms on the heteroaryl or the heteroarylene are each independently selected from O, S or N;
the substituents Ra of each group are each independently selected from deuterium, halogen, nitro, cyano, C 1 -C 4 Alkyl, phenyl, biphenyl, terphenyl or naphthyl.
Preferably Ar 1 Selected from C 6 -C 18 Aryl or C of (2) 5 -C 18 The hydrogen atoms on the aryl and heteroaryl groups each independently may be substituted with Ra;
preferably Ar 2 Selected from C 10 -C 18 Aryl or C of (2) 5 -C 18 The hydrogen atoms on the aryl and heteroaryl groups each independently may be substituted with Ra;
preferably, R is selected from hydrogen, C 6 -C 18 Aryl or C of (2) 3 -C 18 The hydrogen atoms on the aryl and heteroaryl groups each independently may be substituted with Ra;
Preferably L 1 And L 2 Each independently selected from chemical bonds, C 6 -C 18 Arylene or C of (2) 3 -C 18 The hydrogen atoms on the arylene and heteroarylene groups may each independently be substituted with Ra.
More preferably, the Ar 1 Selected from the following groups, unsubstituted or substituted with Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furanyl, benzofuranylA group, dibenzofuranyl, aza-dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, arylamino, carbazolyl.
More preferably, the Ar 2 Selected from the following groups, unsubstituted or substituted with Ra: biphenyl, terphenyl, naphthyl, phenanthryl, triphenylenyl, fluorenyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl.
More preferably, the R is selected from the group consisting of hydrogen, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furanyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, arylamino, carbazolyl.
More preferably, the L 1 And L 2 Each independently selected from the group consisting of chemical bonds, unsubstituted or Ra-substituted subunits of the following compounds: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, pyridine, pyridazine, pyrimidine, pyrazine, quinoline, isoquinoline, quinazoline, quinoxaline, cinnoline, naphthyridine, triazine, pyridopyrazine, furan, benzofuran, dibenzofuran, aza-dibenzofuran, thienylene, benzothiophene, dibenzothiophene, aza-dibenzothiophene, 9-dimethylfluorene, spirofluorene, arylamine, carbazole.
For example, the compound of formula (I) is selected from the following compounds:
the compound adopted by the electron transport material has a parent structure of naphthalene bridging double-absorption fragments, has high bond energy among atoms, good thermal stability, is favorable for solid accumulation among molecules, has strong electron transition capability, and can effectively reduce the driving voltage of an organic electroluminescent device, improve the luminous efficiency of the organic electroluminescent device and prolong the service life of the organic electroluminescent device when used as an electron transport layer material.
A second aspect of the present application provides an electron transport material comprising at least one of the compounds described above.
The derivative of the naphthalene bridging double-suction fragment is applied to an electron transmission layer, has a matched energy level with adjacent layers, is favorable for electron injection and migration, can effectively reduce driving voltage, has higher electron migration rate, and can realize good luminous efficiency in an organic electroluminescent device. The compound provided by the application has a larger conjugate plane, is favorable for molecular accumulation, shows good thermodynamic stability, and shows long service life in an organic electroluminescent device. Meanwhile, the preparation process of the derivative of the naphthalene bridging double-suction fragment is simple and easy to implement, raw materials are easy to obtain, and the method is suitable for industrial production.
A third aspect of the present application provides an organic electroluminescent device comprising at least one of the electron transport materials provided herein as an electron transport layer. Therefore, the organic light-emitting device has the advantages of low driving voltage, high light-emitting efficiency and long service life.
In the present application, the kind and structure of the organic electroluminescent device are not particularly limited, and may be organic electroluminescent devices of different types and structures known in the art, as long as the electron transport materials provided in the present application can be used.
The organic electroluminescent device of the present application may be a light emitting device having a top emission structure, and examples thereof include an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a transparent or semitransparent cathode in this order on a substrate.
The organic electroluminescent device of the present application may be a light emitting device having a bottom light emitting structure, and examples thereof include a transparent or semitransparent anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode structure in this order on a substrate.
The organic electroluminescent device of the present application may be a light emitting device having a double-sided light emitting structure, and examples thereof include a transparent or semitransparent anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a transparent or semitransparent cathode structure sequentially formed on a substrate.
Fig. 1 shows a schematic view of a typical organic electroluminescent device, in which a substrate 1, a reflective anode electrode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, an electron injection layer 7, and a cathode electrode 8 are disposed in this order from bottom to top.
It will be appreciated that fig. 1 schematically illustrates only one typical organic electroluminescent device structure, and the present application is not limited to this structure, and the electron transport material of the present application may be used for any type of organic electroluminescent device. For example, the organic electroluminescent device may further include an electron blocking layer, a hole blocking layer, a light extraction layer, and the like. In practical applications, these layers may be added or omitted as the case may be.
In the organic electroluminescent device of the present application, various materials used for the layer in the prior art may be used for the other layers, except that the electron transport layer contains the electron transport material provided in the present application.
For convenience, the organic electroluminescent device of the present application will be described below with reference to fig. 1, but this is not meant to limit the scope of protection of the present application in any way. It is understood that all organic electroluminescent devices capable of using the electron transport materials of the present application are within the scope of the present application.
In the present application, the substrate 1 is not particularly limited, and a conventional substrate used in an organic electroluminescent device in the related art, for example, glass, a polymer material, glass with a Thin Film Transistor (TFT) element, a polymer material, and the like can be used.
In the present application, the reflective anode electrode 2 is not particularly limited, and may be selected from Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO) 2 ) The transparent conductive material such as zinc oxide (ZnO) may be a metal material such as silver or an alloy thereof, aluminum or an alloy thereof, or an organic conductive material such as PEDOT (poly 3, 4-ethylenedioxythiophene) may be used, and a multilayer structure of the above materials may be used.
In the present application, the material of the hole injection layer 3 is not particularly limited, and may be made of a hole injection layer material known in the art, for example, a Hole Transport Material (HTM) is selected as the hole injection material.
In the present application, the hole injection layer 3 may further include a p-type dopant, the kind of which is not particularly limited, and various p-type dopants known in the art may be employed, for example, the following p-type dopants may be employed:
in the present application, the amount of the p-type dopant is not particularly limited, and may be an amount well known to those skilled in the art.
In the present application, the hole transport layer 4 is not particularly limited, and at least one of Hole Transport Materials (HTM) known in the art may be used.
For example, the material for the hole injection layer host and the material for the hole transport layer may be selected from at least one of the following HT-1 to HT-31 compounds:
in the present application, the light emitting material in the light emitting layer 5 is not particularly limited, and various light emitting materials known to those skilled in the art may be used, for example, the light emitting material may include a host material and a light emitting dye. The host material may be selected from at least one of the following GPH-1 to GPH-80 compounds:
In a preferred embodiment of the present application, the light-emitting layer 5 employs a phosphorescent electroluminescence technique. The light emitting layer 5 thereof contains a phosphorescent dopant which may be selected from at least one of the following RPD-1 to RPD-28 compounds.
The amount of the dopant is not particularly limited and may be an amount well known to those skilled in the art.
In the present application, the electron transport layer 6 comprises at least one of the electron transport materials of the present application, the electron transport layer 6 may also comprise a combination of at least one of the electron transport materials of the present application with at least one of the following known electron transport materials ET-1 to ET-57:
in the present application, the electron transport layer 6 may further include n-type dopants, the kind of which is not particularly limited, and various n-type dopants known in the art may be employed, for example, the following n-type dopants may be employed:
in the present application, the amount of the n-type dopant is not particularly limited, and may be an amount well known to those skilled in the art.
In the present application, the electron injection layer 7 is not particularly limited, and electron injection materials known in the art may be used, for example, may include, but not limited to, liQ, liF, naCl, csF, li in the prior art 2 O、Cs 2 CO 3 At least one of materials such as BaO, na, li, ca.
In the present application, the cathode electrode 8 is not particularly limited, and may be selected from, but not limited to, metals such as magnesium silver mixture, liF/Al, ITO, al, metal mixtures, oxides, and the like.
A fourth aspect of the present application provides a display device comprising the organic electroluminescent device provided herein. Including but not limited to displays, televisions, tablet computers, mobile communication terminals, etc.
The method of preparing the organic electroluminescent device of the present application is not particularly limited, and any method known in the art may be employed, for example, the present application may be prepared using the following preparation method:
(1) Cleaning a reflective anode electrode 2 on an OLED device substrate 1 for top light emission, respectively performing steps of medicine washing, water washing, hairbrushes, high-pressure water washing, air knives and the like in a cleaning machine, and then performing heating treatment;
(2) Vacuum evaporating a hole injection layer 3 on the reflective anode electrode 2, wherein the hole injection layer 3 comprises a main body material and a p-type dopant;
(3) Vacuum evaporating a hole transport material on the hole injection layer 3 as a hole transport layer 4;
(4) Vacuum evaporating a light-emitting layer 5 on the hole transport layer 4, wherein the light-emitting layer 5 comprises a host material and a guest material;
(5) Vacuum evaporating an electron transport material on the light-emitting layer 5 as an electron transport layer 6;
(6) Vacuum evaporating electron injection material selected from LiQ, liF, naCl, csF, li as electron injection layer 7 on electron transport layer 6 2 O、Cs 2 CO 3 One or a combination of a plurality of materials such as BaO, na, li, ca;
(7) A cathode material is vacuum-evaporated on the electron injection layer 7 as a cathode electrode 8.
Only the structure of a typical organic electroluminescent device and a method of manufacturing the same are described above, and it should be understood that the present application is not limited to such a structure. The electron transport material of the present application may be used for an organic electroluminescent device of any structure, and the organic electroluminescent device may be prepared using any preparation method known in the art.
The method for synthesizing the compounds of the present application is not particularly limited, and may be synthesized by any method known to those skilled in the art. The following illustrates the synthesis of the compounds of the present application.
Synthetic examples
Synthesis example 1: synthesis of compound A1:
into a reaction flask were charged 100mmol of 9-phenanthreneboronic acid, 100mmol of 2, 5-dichloropyrimidine, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF) and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 ). The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M1. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% based on 2, 5-dichloropyrimidine.
Into a reaction flask were charged 100mmol of 1-bromo-4-naphthalene boric acid, 100mmol of M1, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh 3 ) 4 . The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M2. Wherein Pd (PPh) 3 ) 4 The amount of (C) added was 1mol% based on M1.
Into a reaction flask were charged 100mmol of 4, 6-diphenyl-2- (4-phenylboronate) triazine, 100mmol of M2, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh 3 ) 4 . The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder A1. Wherein Pd (PPh) 3 ) 4 The amount of (C) added was 1mol% based on M1.
1 H NMR(400MHz,Chloroform)δ9.26(s,1H),8.97(d,J＝7.6,Hz,2H),8.36(s,1H),8.28(s,1H),7.93(d,J＝10.0Hz,2H),7.78(s,1H),7.73(t,J＝8.4Hz,5H),7.69(d,J＝10.0Hz,3H),7.62(d,J＝8.0Hz,4H),7.56-7.40(m,7H),7.34-7.25(m,5H).
Synthesis example 2: synthesis of compound A8:
into a reaction flask were charged 100mmol of 3-pyridineboronic acid, 100mmol of 1, 4-dibromonaphthalene, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh 3 ) 4 . The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M1. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% of 1, 4-dibromonaphthalene.
Into a reaction flask were charged 100mmol of M1, 110mmol of pinacol biborate, 29.4g of potassium acetate (300 mmol), 800ml of dioxane, and 1mol% of dichloro [1,1' -bis (diphenylphosphino) ferrocene]Palladium (Pd (dppf) Cl) 2 ). The reaction was carried out at 100℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, an organic phase is separated, the white solid is obtained by concentration, filtration and water washing, and the obtained solid is recrystallized and purified by toluene to obtain white powder M2. Wherein Pd (dppf) Cl 2 The amount of (C) added was 1mol% based on M1.
Into a reaction flask were charged 100mmol of 2-bromo-5-chloropyridine, 100mmol of M2, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh 3 ) 4 . The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M3. Wherein Pd (PPh) 3 ) 4 The amount of the catalyst to be added was 1mol% of 2-bromo-5-chloropyridine.
Into a reaction flask were charged 100mmol of M3, 100mmol of 4, 6-diphenyl-2- (4-phenylboronate) triazine, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh 3 ) 4 . The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder A8. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% of M3.
1 H NMR(400MHz,Chloroform)δ9.24(s,1H),8.96(d,J＝12.4Hz,2H),8.70(s,1H),8.53–8.19(m,4H),8.01(s,1H),7.96(d,J＝6.8Hz,4H),7.49(d,J＝10.0Hz,8H),7.40-7.25(m,6H).
Synthesis example 3: synthesis of compound a 12:
into a reaction flask were charged 100mmol of 4, 6-diphenyl-2- (4-phenylboronate) triazine, 100mmol of 2, 5-dichloropyrimidine, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF) and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 ). The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M1. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% based on 2, 5-dichloropyrimidine.
Into a reaction flask were charged 100mmol of 1, 4-dibromonaphthalene, 100mmol of 3-pyridineboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF) and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 ). The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M2. Wherein Pd is(PPh 3 ) 4 The amount of (2) added was 1mol% of 1, 4-dibromonaphthalene.
Into a reaction flask were charged 100mmol of M2, 110mmol of pinacol biborate, 29.4g of potassium acetate (300 mmol), 800ml of dioxane, and 1mol% of dichloro [1,1' -bis (diphenylphosphino) ferrocene]Palladium (Pd (dppf) Cl) 2 ). The reaction was carried out at 100℃for 12h. After the reaction, the reaction was stopped, the reaction mixture was cooled to room temperature, water was added, the organic phase was separated, and a white solid was obtained by concentration, filtration and washing with water, and the obtained solid was purified by recrystallization with toluene to obtain white powder M3. Wherein Pd (dppf) Cl 2 The amount of (2) added was 1mol% of M2.
Into a reaction flask were charged 100mmol of M3, 100mmol of M1, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh) 3 ) 4 . The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder A12. Wherein Pd (PPh) 3 ) 4 The amount of (C) added was 1mol% based on M1.
1 H NMR(400MHz,Chloroform)δ9.25(d,J＝10.0Hz,2H),8.97(s,1H),8.70(s,1H),8.34(d,J＝12.0Hz,4H),8.01-7.90(m,6H),7.48(d,J＝12.0Hz,4H),7.40-7.30(m,8H).
Synthesis example 4: synthesis of compound a 15:
into a reaction flask were charged 100mmol of 4, 6-diphenyl-2- (4-phenylboronate) triazine, 100mmol of 1-hydroxy-4-bromodibenzofuran, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF) and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh 3 ) 4 ). The reaction was carried out at 60℃for 12h. Stopping the reaction after the reaction is finished, cooling the reactant to room temperature, adding water, concentrating the organic phase to obtain white solid, filtering, washing the obtained solid with water, and recrystallizing and purifying the obtained solid with tolueneWhite powder M1 was obtained. Wherein Pd (PPh) 3 ) 4 The amount of (2) added is 1mol% of 1-hydroxy-4-bromodibenzofuran.
To the reaction flask were added 100mmol of M1, 100mmol of triethylamine, 200ml of dichloromethane, and 100mmol of trifluoromethanesulfonic anhydride at 0 ℃. Controlling the temperature for 30min, and heating to room temperature for 3h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, and the organic phase was concentrated to give a white solid, which was filtered, washed with water, and dried to give white powder M2.
Into a reaction flask were charged 100mmol of 1, 4-dibromonaphthalene, 100mmol of 3-pyridineboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF) and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 ). The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M3. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% of 1, 4-dibromonaphthalene.
Into a reaction flask were charged 100mmol of M3, 110mmol of pinacol biborate, 29.4g of potassium acetate (300 mmol), 800ml of dioxane, and 1mol% of dichloro [1,1' -bis (diphenylphosphine) ferrocene]Palladium (Pd (dppf) Cl) 2 ). The reaction was carried out at 100℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, the organic phase was separated, and a white solid was obtained by concentration, filtration and washing with water, and the obtained solid was purified by recrystallization with toluene to obtain white powder M4. Wherein Pd (dppf) Cl 2 The amount of (2) added was 1mol% of M3.
Into a reaction flask were charged 100mmol of M2, 100mmol of M4, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh) 3 ) 4 . The reaction was carried out at 60℃for 12h. After the reaction, the reaction was stopped, the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to give a white solid, which was filtered and washed with water, and the obtained solid was purified by recrystallization with toluene to give white powder a15. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% of M2.
1 H NMR(400MHz,Chloroform)δ9.06(s,1H),8.95-8.70(m,3H),8.34(d,J＝10.0Hz,4H),7.97–7.69(m,7H),7.55(d,J＝10.0Hz,4H),7.52(d,J＝12.0Hz,4H),7.44–7.30(m,4H),7.24–7.10(m,3H).
Synthesis example 5: synthesis of compound a 18:
into a reaction flask were charged 100mmol of 3-pyridineboronic acid, 100mmol of 2-bromo-5-chloropyridine, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh 3 ) 4 . The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M1. Wherein Pd (PPh) 3 ) 4 The amount of the catalyst to be added was 1mol% of 2-bromo-5-chloropyridine.
Into a reaction flask were charged 100mmol of M1, 100mmol of 1-bromo-4-naphthalene boric acid, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh 3 ) 4 . The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M2. Wherein Pd (PPh) 3 ) 4 The amount of (C) added was 1mol% based on M1.
Into a reaction flask were charged 100mmol of M2, 100mmol of 4, 6-diphenyl-2- (4-phenylboronate) triazine, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh 3 ) 4 . The reaction was carried out at 60℃for 12h. After the reaction, the reaction was stopped, the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to give a white solid, which was filtered and washed with water, and the obtained solid was purified by recrystallization with toluene to give white powder a18. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% of M2.
1 H NMR(400MHz,Chloroform)δ9.63(s,1H),9.02(s,1H),8.71(d,J＝10.0Hz,2H),8.21(d,J＝8.4Hz,4H),7.96-7.78(m,4H),7.67-7.56(m,6H),7.49(d,J＝12.0Hz,4H),7.40-7.25(m,5H).
Synthesis example 6: synthesis of compound a 19:
into a reaction flask were charged 100mmol of 3-pyridineboronic acid, 100mmol of 1, 4-dibromonaphthalene, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh 3 ) 4 . The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M1. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% of 1, 4-dibromonaphthalene.
Into a reaction flask were charged 100mmol of M1, 110mmol of pinacol biborate, 29.4g of potassium acetate (300 mmol), 800ml of dioxane, and 1mol% of dichloro [1,1' -bis (diphenylphosphino) ferrocene ]Palladium (Pd (dppf) Cl) 2 ). The reaction was carried out at 100℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, an organic phase is separated, the white solid is obtained by concentration, filtration and water washing, and the obtained solid is recrystallized and purified by toluene to obtain white powder M2. Wherein Pd (dppf) Cl 2 The amount of (C) added was 1mol% based on M1.
Into a reaction flask were charged 100mmol of 2-bromo-5-chloropyridine, 100mmol of M2, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh 3 ) 4 . The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M3. Wherein Pd (PPh) 3 ) 4 The amount of the catalyst to be added was 1mol% of 2-bromo-5-chloropyridine.
Into a reaction flask were charged 100mmol of M3, 110mmol of pinacol biborate, 29.4g of potassium acetate (300 mmol), 800ml of dioxane, and 1mol% of dichloro [1,1' -bis (diphenylphosphine) ferrocene]Palladium (Pd (dppf) Cl) 2 ). The reaction was carried out at 100℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, the organic phase was separated, and a white solid was obtained by concentration, filtration and washing with water, and the obtained solid was purified by recrystallization with toluene to obtain white powder M4. Wherein Pd (dppf) Cl 2 The amount of (2) added was 1mol% of M3.
Into a reaction flask were charged 100mmol of 2-phenyl-4, 6-dichlorotriazine, 100mmol of 9, 9-dimethylfluorene-2-boronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh 3 ) 4 . The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M5. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% of 2-phenyl-4, 6-dichlorotriazine.
Into a reaction flask were charged 100mmol of M4, 100mmol of M5, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh) 3 ) 4 . The reaction was carried out at 60℃for 12h. After the reaction, the reaction was stopped, the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to give a white solid, which was filtered and washed with water, and the obtained solid was purified by recrystallization with toluene to give white powder a19. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% of M4.
1 H NMR(400MHz,Chloroform)δ9.02(s,1H),8.95-8.70(m,3H),8.34(d,J＝10.0Hz,3H),8.03(d,J＝10.0Hz,3H),7.84(d,J＝8.0Hz,4H),7.61–7.42(m,6H),7.34(d,J＝8.4Hz,2H),7.25–7.12(m,4H),1.69(s,6H).
Synthesis example 7: synthesis of compound a 20:
into a reaction flask were charged 100mmol of 2-chloro-4, 6-diphenyltriazine, 100mmol of 4-chlorobenzeneboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF) and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh 3 ) 4 ). The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M1. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% of 2-chloro-4, 6-diphenyltriazine.
Into a reaction flask were charged 100mmol of M1, 110mmol of pinacol biborate, 29.4g of potassium acetate (300 mmol), 800ml of dioxane, and 1mol% of dichloro [1,1' -bis (diphenylphosphino) ferrocene]Palladium (Pd (dppf) Cl) 2 ). The reaction was carried out at 100℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, an organic phase is separated, the white solid is obtained by concentration, filtration and water washing, and the obtained solid is recrystallized and purified by toluene to obtain white powder M2. Wherein Pd (dppf) Cl 2 The amount of (C) added was 1mol% based on M1.
Into a reaction flask were charged 100mmol of 1-bromo-3-chloro-5-iodobenzene, 100mmol of 4-pyridineboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh 3 ) 4 . The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M3. Wherein Pd (PPh) 3 ) 4 The amount of the catalyst to be added was 1mol% of 1-bromo-3-chloro-5-iodobenzene.
Into a reaction flask were charged 100mmol of 1, 4-dibromonaphthalene, 100mmol of 3-pyridineboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF) and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 ). The reaction was carried out at 60℃for 12h. Stopping the reaction after the reaction is finished, cooling the reactant to room temperature, adding water, and concentrating the organic phase to obtain whiteThe solid was filtered and washed with water, and the obtained solid was purified by recrystallization from toluene to obtain white powder M4. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% of 1, 4-dibromonaphthalene.
Into a reaction flask were charged 100mmol of M4, 110mmol of pinacol biborate, 29.4g of potassium acetate (300 mmol), 800ml of dioxane, and 1mol% of dichloro [1,1' -bis (diphenylphosphino) ferrocene]Palladium (Pd (dppf) Cl) 2 ). The reaction was carried out at 100℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, the organic phase was separated, and a white solid was obtained by concentration, filtration and washing with water, and the obtained solid was purified by recrystallization with toluene to obtain white powder M5. Wherein Pd (dppf) Cl 2 The amount of (2) added was 1mol% of M4.
Into a reaction flask were charged 100mmol of M3, 100mmol of M5, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh) 3 ) 4 . The reaction was carried out at 60℃for 12h. After the reaction, the reaction was stopped, the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to give a white solid, which was filtered and washed with water, and the obtained solid was purified by recrystallization with toluene to give white powder M6. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% of M3.
Into a reaction flask were charged 100mmol of M2, 100mmol of M6, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh) 3 ) 4 . The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder A20. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% of M2.
1 H NMR(400MHz,Chloroform)δ9.24(s,2H),8.70(d,J＝8.0Hz,2H),8.34(d,J＝10.0Hz,4H),8.27–8.11(m,3H),8.08–7.72(m,6H),7.57(s,1H),7.56(s,1H),7.49(d,J＝10.0Hz,6H),7.43-7.35(m,6H).
Synthesis example 8: synthesis of compound a 23:
into a reaction flask were charged 100mmol of lyxolidine, 100mmol of 9-phenanthreneboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh 3 ) 4 . The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M1. Wherein Pd (PPh) 3 ) 4 The addition amount of (2) is 1mol% of that of the cyprodinil.
Into a reaction flask were charged 100mmol of M1, 100mmol of 4-chlorophenylboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh 3 ) 4 . The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M2. Wherein Pd (PPh) 3 ) 4 The amount of (C) added was 1mol% based on M1.
Into a reaction flask were charged 100mmol of M2, 110mmol of pinacol biborate, 29.4g of potassium acetate (300 mmol), 800ml of dioxane, and 1mol% of dichloro [1,1' -bis (diphenylphosphino) ferrocene]Palladium (Pd (dppf) Cl) 2 ). The reaction was carried out at 100℃for 12h. After the reaction, the reaction was stopped, the reaction mixture was cooled to room temperature, water was added, the organic phase was separated, and a white solid was obtained by concentration, filtration and washing with water, and the obtained solid was purified by recrystallization with toluene to obtain white powder M3. Wherein Pd (dppf) Cl 2 The amount of (2) added was 1mol% of M2.
Into a reaction flask were charged 100mmol of 1, 4-dibromonaphthalene, 100mmol of 3-pyridineboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh 3 ) 4 . The reaction was carried out at 60℃for 12h. Stopping the reaction after the reaction is finished, cooling the reactant to room temperature, adding water, concentrating the organic phase to obtain white solid, filtering and washing the white solid to obtainThe solid obtained was purified by recrystallization from toluene to give white powder M4. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% based on 2, 5-dichloropyrimidine.
Into a reaction flask were charged 100mmol of M3, 100mmol of M4, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh) 3 ) 4 . The reaction was carried out at 60℃for 12h. After the reaction, the reaction was stopped, the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to give a white solid, which was filtered and washed with water, and the obtained solid was purified by recrystallization with toluene to give white powder a23. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% of M3.
1 H NMR(400MHz,Chloroform)δ9.24(s,1H),8.97(d,J＝7.6Hz,2H),8.84(s,1H),8.77(d,J＝10.0Hz,3H),8.49–8.37(m,3H),7.90-7.78(m,4H),7.69(d,J＝10.0Hz,6H),7.48(d,J＝12.0Hz,4H),7.40-7.28(m,4H).
Synthesis example 9: synthesis of compound a 26:
into a reaction flask were charged 100mmol of 2-chloro-3, 5-diphenylpyrimidine, 100mmol of 3-chlorobenzeneboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF) and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh 3 ) 4 ). The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M1. Wherein Pd (PPh) 3 ) 4 The amount of the catalyst to be added was 1mol% of 2-chloro-3, 5-diphenylpyrimidine.
Into a reaction flask were charged 100mmol of M1, 110mmol of pinacol biborate, 29.4g of potassium acetate (300 mmol), 800ml of dioxane, and 1mol% of dichloro [1,1' -bis (diphenylphosphino) ferrocene]Palladium (Pd (dppf) Cl) 2 ). The reaction was carried out at 100℃for 12h. Stopping the reaction after the reaction is completed, and cooling the reactant to room temperatureAdding water, separating organic phase, concentrating to obtain white solid, filtering, washing with water, and recrystallizing and purifying the obtained solid with toluene to obtain white powder M2. Wherein Pd (dppf) Cl 2 The amount of (C) added was 1mol% based on M1.
Into a reaction flask were charged 100mmol of 1-bromo-3-chloro-5-iodobenzene, 100mmol of 4-cyanobenzeneboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh 3 ) 4 . The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M3. Wherein Pd (PPh) 3 ) 4 The amount of the catalyst to be added was 1mol% of 1-bromo-3-chloro-5-iodobenzene.
Into a reaction flask were charged 100mmol of 1, 4-dibromonaphthalene, 100mmol of 3-pyridineboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF) and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 ). The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M4. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% of 1, 4-dibromonaphthalene.
Into a reaction flask were charged 100mmol of M4, 110mmol of pinacol biborate, 29.4g of potassium acetate (300 mmol), 800ml of dioxane, and 1mol% of dichloro [1,1' -bis (diphenylphosphino) ferrocene]Palladium (Pd (dppf) Cl) 2 ). The reaction was carried out at 100℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, the organic phase was separated, and a white solid was obtained by concentration, filtration and washing with water, and the obtained solid was purified by recrystallization with toluene to obtain white powder M5. Wherein Pd (dppf) Cl 2 The amount of (2) added was 1mol% of M4.
Into a reaction flask were charged 100mmol of M3, 100mmol of M5, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh) 3 ) 4 . The reaction was carried out at 60℃for 12h. Reverse-rotationAfter the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, and the organic phase was concentrated to give a white solid, which was filtered and washed with water, and the obtained solid was purified by recrystallization with toluene to give white powder M6. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% of M3.
Into a reaction flask were charged 100mmol of M2, 100mmol of M6, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh) 3 ) 4 . The reaction was carried out at 60℃for 12h. After the reaction, the reaction was stopped, the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to give a white solid, which was filtered and washed with water, and the obtained solid was purified by recrystallization with toluene to give white powder a26. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% of M2.
1 H NMR(400MHz,Chloroform)δ9.24(s,1H),9.02(s,1H),8.52–8.29(m,3H),8.24(t,J＝7.2Hz,4H),7.94(d,J＝8.0Hz,2H),7.84-7.70(m,5H),7.61(s,1H),7.56(d,J＝8.0Hz,4H),7.48(d,J＝10.0Hz,4H),7.40-7.24(m,7H).
Synthesis example 10: synthesis of compound a 36:
into a reaction flask were charged 100mmol of lyzidine, 100mmol of phenylboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF) and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh 3 ) 4 ). The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M1. Wherein Pd (PPh) 3 ) 4 The addition amount of (2) is 1mol% of that of the cyprodinil.
Into a reaction flask were charged 100mmol of M1, 100mmol of 3-chlorobenzeneboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF) and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 ). The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M2. Wherein Pd (PPh) 3 ) 4 The amount of (C) added was 1mol% based on M1.
Into a reaction flask were charged 100mmol of M2, 110mmol of pinacol biborate, 29.4g of potassium acetate (300 mmol), 800ml of dioxane, and 1mol% of dichloro [1,1' -bis (diphenylphosphino) ferrocene]Palladium (Pd (dppf) Cl) 2 ). The reaction was carried out at 100℃for 12h. After the reaction, the reaction was stopped, the reaction mixture was cooled to room temperature, water was added, the organic phase was separated, and a white solid was obtained by concentration, filtration and washing with water, and the obtained solid was purified by recrystallization with toluene to obtain white powder M3. Wherein Pd (dppf) Cl 2 The amount of (2) added was 1mol% of M2.
Into a reaction flask were charged 100mmol of 2-chloro-4-phenylquinazoline, 100mmol of 4-chlorophenylboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh) 3 ) 4 . The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M4. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% based on 2-chloro-4-phenylquinazoline.
Into a reaction flask were charged 100mmol of 1-bromo-4-naphthalene boric acid, 100mmol of M4, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF) and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 ). The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M5. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% of 1-bromo-4-naphthaleneboric acid.
Into a reaction flask were charged 100mmol of M3, 100mmol of M5, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water and 1mol% Pd (PPh 3 ) 4 . The reaction was carried out at 60℃for 12h. After the reaction, the reaction was stopped, the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to give a white solid, which was filtered and washed with water, and the obtained solid was purified by recrystallization with toluene to give white powder a36. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% of M2.
1 H NMR(400MHz,Chloroform)δ9.00(s,1H),8.35-8.23(m,3H),7.95(t,J＝8.4Hz,3H),7.80(d,J＝9.6Hz,4H),7.75-7.62(m,5H),7.55(d,J＝7.6Hz,6H),7.49(d,J＝8.0Hz,4H),7.33(s,2H),7.26(d,J＝10.0Hz,7H).
Synthesis example 11: synthesis of compound a 37:
into a reaction flask were charged 100mmol of 2, 4-dichloro-6-phenylpyrimidine, 100mmol of 2-naphthaleneboric acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF) and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh 3 ) 4 ). The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M1. Wherein Pd (PPh) 3 ) 4 The amount of (2), 4-dichloro-6-phenylpyrimidine added was 1mol%.
Into a reaction flask were charged 100mmol of M1, 100mmol of 4-chlorophenylboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF) and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 ). The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M2. Wherein Pd (PPh) 3 ) 4 The amount of (C) added was 1mol% based on M1.
Into a reaction flask was charged 100mmolM2, 110mmol of pinacol bisborate, 29.4g of potassium acetate (300 mmol), 800ml of dioxane, and 1mol% of dichloro [1,1' -bis (diphenylphosphine) ferrocene]Palladium (Pd (dppf) Cl) 2 ). The reaction was carried out at 100℃for 12h. After the reaction, the reaction was stopped, the reaction mixture was cooled to room temperature, water was added, the organic phase was separated, and a white solid was obtained by concentration, filtration and washing with water, and the obtained solid was purified by recrystallization with toluene to obtain white powder M3. Wherein Pd (dppf) Cl 2 The amount of (2) added was 1mol% of M2.
Into a reaction flask were charged 100mmol of 2, 4-dichloroquinazoline, 100mmol of triethylaluminum, 800ml of THF, and 1mol% of Pd (PPh 3 ) 4 . The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M4. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% based on 2, 4-dichloroquinazoline.
Into a reaction flask were charged 100mmol of 1-bromo-4-naphthalene boric acid, 100mmol of M4, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF) and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 ). The reaction was carried out at 60℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M5. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% of 1-bromo-4-naphthaleneboric acid.
Into a reaction flask were charged 100mmol of M3, 100mmol of M5, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh) 3 ) 4 . The reaction was carried out at 60℃for 12h. After the reaction, the reaction was stopped, the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to give a white solid, which was filtered and washed with water, and the obtained solid was purified by recrystallization with toluene to give white powder a37. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% of M3.
1 H NMR(400MHz,Chloroform)δ8.95(s,1H),8.46-8.23(m,3H),8.08–7.97(m,5H),7.86(d,J＝8.8Hz,2H),7.84–7.67(m,3H),7.64–7.59(m,6H),7.53(d,J＝9.2Hz,4H),7.42-7.34(m,3H),3.07(m,3H),1.32(m,2H).
Other compounds of the present application can be synthesized by selecting appropriate raw materials according to the concept of synthesis examples 1-11, and any other appropriate methods and raw materials can be selected for synthesis.
Example 1
Ultrasonic treating the glass plate coated with the ITO transparent conductive layer in a commercial cleaning agent, flushing in deionized water, ultrasonic degreasing in an acetone-ethanol mixed solvent, baking in a clean environment until water is completely removed, cleaning with ultraviolet light and ozone, and bombarding the surface with a low-energy cation beam;
then placing the above-mentioned glass substrate with anode in vacuum cavity, vacuumizing to less than 10 -5 And vacuum evaporating a hole injection layer on the anode layer film, wherein the hole injection layer is made of HT-11 and 3% of p-type dopant (p-1) by mass ratio, the evaporation rate is 0.1nm/s, the evaporation film thickness is 10nm, and the hole injection layer is made of HT-11 and the p-type dopant (p-1) as follows:
Then, a hole transport material HT-5 material was vacuum-evaporated as a hole transport layer on top of the hole injection layer, wherein the evaporation rate was 0.1nm/s, the evaporation film thickness was 80nm, and the hole transport layer material HT-5 was as follows:
then, a light-emitting layer is vacuum-evaporated on the hole transport layer, the light-emitting layer comprises a host material GHP-16 and a guest material RPD-1, evaporation is carried out by utilizing a multi-source co-evaporation method, wherein the evaporation rate of the host material GHP-16 is regulated to be 0.1nm/s, the evaporation rate of the dye RPD-1 is 3% of the evaporation rate of the host material, the total film thickness of the evaporation is 30nm, and the host material GHP-16 and the guest material PRD-1 are as follows:
then, an electron transport layer including an electron transport material A1 is vacuum-deposited over the light-emitting layer. Wherein, the vapor deposition rate is 0.1nm/s, the vapor deposition film thickness is 30nm, and the selected electron transport material A1 is as follows:
then, liF with the thickness of 0.5nm is vacuum evaporated on the electron transport layer to be used as an electron injection layer, wherein the evaporation rate is 0.1nm/s, and the thickness of the evaporation film is 10nm;
then, an Al layer having a thickness of 150nm was vacuum-deposited on the electron injection layer as a cathode electrode of the organic electroluminescent device, wherein the deposition rate was 1nm/s and the deposition film thickness was 50nm.
Examples 2 to 11
The procedure of example 1 was repeated except that A8, A12, A15, A18, A19, A20, A23, A26, A36 and A37 were used in place of A1. See in particular table 1.
Comparative example 1
The procedure of example 1 was repeated except that ET-2 was used instead of A1.
The organic electroluminescent device prepared by the above procedure was subjected to the following performance measurement:
the driving voltage and current efficiency and the lifetime of the organic electroluminescent devices prepared in examples 1 to 11 and comparative example 1 were measured using a digital source meter and a luminance meter under the same luminance, specifically, the voltage was increased at a rate of 0.1V per second, and the luminance of the organic electroluminescent device was measured to be 5000cd/m 2 The voltage at the time is the driving voltage, and the current density at the time is measured; the ratio of brightness to current density is the current efficiency; the lifetime test of LT95 is as follows: at 5000cd/m using a luminance meter 2 Under the condition of brightness, constant current is kept, and the brightness of the organic electroluminescent device is measured to be reduced to 4750cd/m 2 Time in hours.
TABLE 1 organic electroluminescent device Performance results
From table 1, it can be seen that the compounds A1, A8, a12, a15, a18, a19, a20, a23, a26, a36 and a37 prepared by the method are used for the electron transport material of the organic electroluminescent device, can effectively reduce the driving voltage, improve the current efficiency, prolong the service life of the device, and are electron transport materials with good performance.
The foregoing description is only of the preferred embodiments of the present application and is not intended to limit the scope of the present application. Any modifications, equivalent substitutions, improvements, etc. that are within the spirit and principles of the present application are intended to be included within the scope of the present application.
Claims (10)
1. A compound of formula (I):
wherein, the liquid crystal display device comprises a liquid crystal display device,
Ar 1 selected from C 6 -C 30 Aryl or C of (2) 5 -C 30 The hydrogen atoms on the aryl and heteroaryl groups each independently may be substituted with Ra;
Ar 2 selected from C 10 -C 30 Aryl or C of (2) 5 -C 30 The hydrogen atoms on the aryl and heteroaryl groups each independently may be substituted with Ra;
X 1 -X 3 selected from CH or N, and at least two selected from N;
Y 1 -Y 5 selected from CR or N, and at least one selected from N, R is selected from hydrogen, C 6 -C 30 Aryl or C of (2) 3 -C 30 Adjacent R may form a ring, and the hydrogen atoms on the aryl and heteroaryl groups may each independently be substituted with Ra;
L 1 and L 2 Each independently selected from chemical bonds, C 6 -C 30 Arylene or C of (2) 3 -C 30 The hydrogen atoms on the arylene and heteroarylene groups each independently may be substituted with Ra;
the heteroatoms on the heteroaryl or the heteroarylene are each independently selected from O, S or N;
the substituents Ra of each group are each independently selected from deuterium, halogen, nitro, cyano, C 1 -C 4 Alkyl, phenyl, biphenyl, terphenyl or naphthyl.
2. A compound according to claim 1, wherein,
Ar 1 selected from C 6 -C 18 Aryl or C of (2) 5 -C 18 The hydrogen atoms on the aryl and heteroaryl groups each independently may be substituted with Ra;
Ar 2 selected from C 10 -C 18 Aryl or C of (2) 5 -C 18 The hydrogen atoms on the aryl and heteroaryl groups each independently may be substituted with Ra;
L 1 and L 2 Each independently selected from chemical bonds, C 6 -C 18 Arylene or C of (2) 3 -C 18 The hydrogen atoms on the arylene and heteroarylene groups each independently may be substituted with Ra;
r is selected from hydrogen, C 6 -C 18 Aryl or C of (2) 3 -C 18 Heteroaryl of (C), said aryl andthe hydrogen atoms on the heteroaryl groups may each independently be substituted with Ra.
3. The compound according to claim 1, wherein Ar 1 Selected from the following groups, unsubstituted or substituted with Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furanyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, arylamino, carbazolyl.
4. The compound according to claim 1, wherein Ar 2 Selected from the following groups, unsubstituted or substituted with Ra: biphenyl, terphenyl, naphthyl, phenanthryl, triphenylenyl, fluorenyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl.
5. A compound according to claim 1, wherein R is selected from hydrogen, the following groups unsubstituted or substituted with Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furanyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, arylamino, carbazolyl.
6. A compound according to claim 1 whereinThe L is 1 And L 2 Each independently selected from the group consisting of chemical bonds, unsubstituted or Ra-substituted subunits of the following compounds: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, pyridine, pyridazine, pyrimidine, pyrazine, quinoline, isoquinoline, quinazoline, quinoxaline, cinnoline, naphthyridine, triazine, pyridopyrazine, furan, benzofuran, dibenzofuran, aza-dibenzofuran, thienylene, benzothiophene, dibenzothiophene, aza-dibenzothiophene, 9-dimethylfluorene, spirofluorene, arylamine, carbazole.
7. The compound according to claim 1, wherein the compound is selected from the group consisting of:
8. an electron transport material comprising at least one of the compounds of any of claims 1-7.
9. An organic electroluminescent device comprising at least one of the electron transporting materials of claim 8.
10. A display device comprising the organic electroluminescent device of claim 9.
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| CN105339363A (en) * | 2013-06-28 | 2016-02-17 | 株式会社Lg化学 | Hetero ring compound and organic light emitting diode comprising same |
| CN107635978A (en) * | 2016-01-26 | 2018-01-26 | 株式会社Lg化学 | Heterocyclic compound and the organic luminescent device for including it |
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