CN116514732A - Organic compound, and electronic component and electronic device including the same - Google Patents
Organic compound, and electronic component and electronic device including the same Download PDFInfo
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- CN116514732A CN116514732A CN202211150170.9A CN202211150170A CN116514732A CN 116514732 A CN116514732 A CN 116514732A CN 202211150170 A CN202211150170 A CN 202211150170A CN 116514732 A CN116514732 A CN 116514732A
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 92
- 239000010410 layer Substances 0.000 claims description 72
- 125000003118 aryl group Chemical group 0.000 claims description 57
- 125000001424 substituent group Chemical group 0.000 claims description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
- -1 spirobifluorenyl Chemical group 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 26
- 229910052805 deuterium Inorganic materials 0.000 claims description 25
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 239000011737 fluorine Substances 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 239000002346 layers by function Substances 0.000 claims description 12
- 125000000732 arylene group Chemical group 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 8
- 125000005549 heteroarylene group Chemical group 0.000 claims description 8
- 239000004305 biphenyl Substances 0.000 claims description 7
- 235000010290 biphenyl Nutrition 0.000 claims description 7
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000005561 phenanthryl group Chemical group 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 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 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 4
- 125000005567 fluorenylene group Chemical group 0.000 claims description 4
- 125000004957 naphthylene group Chemical group 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000004653 anthracenylene group Chemical group 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000005562 phenanthrylene group Chemical group 0.000 claims description 3
- 125000001725 pyrenyl group Chemical group 0.000 claims description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims 1
- 125000005580 triphenylene group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 238000002347 injection Methods 0.000 description 14
- 239000007924 injection Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000002994 raw material Substances 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 230000005525 hole transport Effects 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical class C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 10
- 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 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 239000002019 doping agent Substances 0.000 description 8
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 230000000903 blocking effect Effects 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- 229920001090 Polyaminopropyl biguanide Polymers 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 2
- XYQOOBSGDHIYLN-UHFFFAOYSA-N 1-phenyladamantan-2-one Chemical class O=C1C(C2)CC(C3)CC2CC13C1=CC=CC=C1 XYQOOBSGDHIYLN-UHFFFAOYSA-N 0.000 description 2
- CXHXFDQEFKFYQJ-UHFFFAOYSA-N 2-bromo-4-chloro-1-iodobenzene Chemical compound ClC1=CC=C(I)C(Br)=C1 CXHXFDQEFKFYQJ-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- QAOXJQGZIOPYSG-UHFFFAOYSA-N 5-phenyladamantan-2-one Chemical compound O=C1C(C2)CC(C3)CC1CC32C1=CC=CC=C1 QAOXJQGZIOPYSG-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 150000001721 carbon Chemical class 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- 150000001975 deuterium Chemical group 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical group C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 125000004306 triazinyl group Chemical group 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000764238 Isis Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000010009 beating Methods 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000005566 carbazolylene group Chemical group 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- UFQGSPKFLBLFAY-UHFFFAOYSA-N cyclohexane cyclopentane Chemical compound C1CCCCC1.C1CCCCC1.C1CCCC1 UFQGSPKFLBLFAY-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002704 decyl 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])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005345 deuteroalkyl group Chemical group 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- TZBDEVBNMSLVKT-UHFFFAOYSA-N idramantone Chemical compound C1C(C2)CC3CC1(O)CC2C3=O TZBDEVBNMSLVKT-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 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
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 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
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical group C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 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
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 125000005649 substituted arylene group Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 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
- 229930192474 thiophene Natural products 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
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 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
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present application relates to an organic compound, and an electronic component and an electronic device including the same. The structural formula of the organic compound is shown as formula 1, and the organic compound can be applied to an organic electroluminescent device, so that the performance of the device can be remarkably improved.
Description
Technical Field
The application belongs to the technical field of organic materials, and particularly relates to an organic compound, an electronic element comprising the same and an electronic device.
Background
With the development of electronic technology and the advancement of material science, the range of applications of electronic components for realizing electroluminescence or photoelectric conversion is becoming wider and wider. Such electronic components typically include oppositely disposed cathodes and anodes, and a functional layer disposed between the cathodes and anodes. The functional layer is composed of a plurality of organic or inorganic film layers and generally includes an energy conversion layer, a hole transport layer between the energy conversion layer and the anode, and an electron transport layer between the energy conversion layer and the cathode.
For example, when the electronic component is an organic electroluminescent device, it generally includes an anode, a hole transport layer, an electroluminescent layer as an energy conversion layer, an electron transport layer, and a cathode, which are sequentially stacked. When voltage is applied to the cathode and the anode, the two electrodes generate an electric field, electrons at the cathode side move to the electroluminescent layer under the action of the electric field, holes at the anode side also move to the luminescent layer, the electrons and the holes are combined in the electroluminescent layer to form excitons, and the excitons are in an excited state to release energy outwards, so that the electroluminescent layer emits light outwards.
In general, the electron transport material has poor stability and low transport efficiency, and when used in an organic electroluminescent device, the electron transport material cannot truly balance hole electron transport, so that the luminous efficiency of the device is reduced, and the service life of the device is shortened.
At present, although a large number of organic electroluminescent materials with excellent performance have been developed, it is still necessary to continue to develop new materials to further improve the performance of electronic components.
Disclosure of Invention
In view of the foregoing problems of the prior art, it is an object of the present application to provide an organic compound, which can improve the performance of electronic components and electronic devices, such as improving the efficiency and lifetime of devices, and electronic components and electronic devices including the same.
In order to achieve the above object, the present application adopts the following technical scheme:
according to a first aspect of the present application, there is provided an organic compound having a structure represented by formula 1:
Ar 3 is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms;
Ar 3 the substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano, alkyl group with 1-5 carbon atoms or phenyl group;
X 1 、X 2 and X 3 Represents a C (H) or N atom, and X 1 、X 2 And X 3 At least one of which is an N atom;
L、L 1 and L 2 The same or different, each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms;
Ar 1 and Ar is a group 2 The same or different, each independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms and substituted or unsubstituted heteroaryl groups having 5 to 30 carbon atoms;
L、L 1 、L 2 、Ar 1 and Ar is a group 2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, deuterated alkyl with 1-10 carbon atoms, trialkylsilyl with 3-12 carbon atoms, aryl with 6-20 carbon atoms, heteroaryl with 5-15 carbon atoms or cycloalkyl with 3-10 carbon atoms;
optionally in Ar 1 And Ar is a group 2 Any two adjacent substituents form a ring;
R 1 and R is 2 The two groups are identical or different and are each independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1-10 carbon atoms, halogenated alkyl groups with 1-10 carbon atoms, deuterated alkyl groups with 1-10 carbon atoms and aryl groups with 6-20 carbon atoms;
n 1 r represents 1 And is selected from 0, 1,2, 3 or 4; when n is 1 When the number is greater than 1, any two R 1 The same or different;
n 2 r represents 2 And is selected from 0, 1,2 or 3; when n is 2 When the number is greater than 1, any two R 2 The same or different.
According to a second aspect of the present application, there is provided an electronic component comprising an anode and a cathode arranged opposite each other, and a functional layer provided between the anode and the cathode; the functional layer comprises the organic compound.
According to a third aspect of the present application, there is provided an electronic device comprising the electronic element of the second aspect.
The organic compound of the present application is formed by combining an aryl-substituted adamantane group with a triazine group, and generally, has excellent thermal stability for adamantane because of its excellent sublimation due to its large space and robustness, and has a stable chemical structure; while the aryl group substituted with the hydrogen on adamantane can saturate the substituted carbon, the stability is further enhanced, and the combination with the triazine group can significantly improve the device and the efficiency and the service life.
Additional features and advantages of the present application will be set forth in the detailed description which follows.
Drawings
The accompanying drawings are included to provide a further understanding of the application and are incorporated in and constitute a part of this specification, illustrate the application and, together with the description, do not limit the application.
Fig. 1 is a schematic structural view of an organic electroluminescent device of the present application.
Fig. 2 is a schematic structural diagram of an electronic device of the present application.
Reference numerals
100. Anode 200, cathode 300, functional layer 310, and hole injection layer
320. Hole transport layer 330, electron blocking layer 340, organic light emitting layer 350, and electron transport layer
360. Electron injection layer 400 and electronic device
Detailed Description
Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments may be embodied in many forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of the exemplary embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the present application.
In a first aspect, the present application provides an organic compound having a structure represented by formula 1:
Ar 3 is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms;
Ar 3 the substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano, alkyl group with 1-5 carbon atoms or phenyl group;
X 1 、X 2 and X 3 Represents a C (H) or N atom, and X 1 、X 2 And X 3 At least one of which is an N atom;
L、L 1 and L 2 The same or different, each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms;
Ar 1 and Ar is a group 2 Identical or different, each independentlyA substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms;
L、L 1 、L 2 、Ar 1 and Ar is a group 2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, deuterated alkyl with 1-10 carbon atoms, trialkylsilyl with 3-12 carbon atoms, aryl with 6-20 carbon atoms, heteroaryl with 5-15 carbon atoms or cycloalkyl with 3-10 carbon atoms;
optionally in Ar 1 And Ar is a group 2 Any two adjacent substituents form a ring;
R 1 and R is 2 The two groups are identical or different and are each independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1-10 carbon atoms, halogenated alkyl groups with 1-10 carbon atoms, deuterated alkyl groups with 1-10 carbon atoms and aryl groups with 6-20 carbon atoms;
n 1 r represents 1 And is selected from 0, 1,2, 3 or 4; when n is 1 When the number is greater than 1, any two R 1 The same or different;
n 2 r represents 2 And is selected from 0, 1,2 or 3; when n is 2 When the number is greater than 1, any two R 2 The same or different.
In the present application, the fluorenyl group may be substituted with 1 or 2 substituents, wherein, in the case where the above fluorenyl group is substituted, it may be:and the like, but is not limited thereto.
In this application, the descriptions "each … … is independently" and "… … is independently" and "… … is independently selected from" may be interchanged, and should be understood in a broad sense, which refers to that specific options expressed between the same symbols in different groups do not affect each other, or that specific options expressed between the same symbols in the same groups do not affect each other. For example, the number of the cells to be processed,wherein each q is independently 0, 1,2 or 3, and each R "is independently selected from hydrogen, deuterium, fluorine, chlorine", with the meaning: the formula Q-1 represents Q substituent groups R ' on the benzene ring, wherein R ' can be the same or different, and the options of each R ' are not mutually influenced; the formula Q-2 represents that each benzene ring of the biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on two benzene rings can be the same or different, each R 'can be the same or different, and the options of each R' are not influenced each other.
In the present application, such terms as "substituted or unsubstituted" mean that the functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to aryl having a substituent Rc or unsubstituted aryl. Wherein the substituent Rc may be, for example, deuterium, a halogen group, cyano, heteroaryl, aryl, trialkylsilyl, alkyl, haloalkyl, deuteroalkyl, cycloalkyl, etc.
In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to all the numbers of carbon atoms. For example, if L 1 Is a substituted arylene group having 12 carbon atoms, then the arylene group and all of the substituents thereon have 12 carbon atoms.
Aryl in this application refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group may be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups connected by a carbon-carbon bond conjugate, a monocyclic aryl group and a condensed ring aryl group connected by a carbon-carbon bond conjugate, two or more condensed ring aryl groups connected by a carbon-carbon bond conjugate. That is, two or more aromatic groups conjugated through carbon-carbon bonds may also be considered aryl groups herein unless otherwise indicated. Among them, the condensed ring aryl group may include, for example, a bicyclic condensed aryl group (e.g., naphthyl group), a tricyclic condensed aryl group (e.g., phenanthryl group, fluorenyl group, anthracenyl group), and the like. The aryl group does not contain B, N,O, S, P, se and Si. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl,Radicals, spirobifluorenyl radicals, and the like. As used herein, arylene refers to a divalent group formed by the further loss of one hydrogen atom from an aryl group.
In the present application, terphenyl includes
In the present application, a substituted aryl group may be one in which one or two or more hydrogen atoms in the aryl group are substituted with a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, an alkyl group, a cycloalkyl group, or the like. It is understood that the number of carbon atoms of a substituted aryl refers to the total number of carbon atoms of the aryl and substituents on the aryl, e.g., a substituted aryl having 18 carbon atoms refers to the total number of carbon atoms of the aryl and substituents being 18.
Heteroaryl in this application refers to a monovalent aromatic ring or derivative thereof containing 1,2, 3,4, 5, 6 or 7 heteroatoms in the ring, which may be at least one of B, O, N, P, si, se and S. Heteroaryl groups may be monocyclic heteroaryl or polycyclic heteroaryl, in other words, heteroaryl groups may be a single aromatic ring system or multiple aromatic ring systems that are conjugated through carbon-carbon bonds, with either aromatic ring system being an aromatic monocyclic ring or an aromatic fused ring. Illustratively, heteroaryl groups may include, but are not limited to, thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthroline, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, and the like. Wherein thienyl, furyl, phenanthroline and the like are heteroaryl groups of a single aromatic ring system type, and N-phenylcarbazolyl and N-pyridylcarbazolyl are heteroaryl groups of a polycyclic ring system type which are conjugated and connected through carbon-carbon bonds. In the present application, the term "heteroarylene" refers to a divalent group formed by further losing one hydrogen atom.
In the present application, a substituted heteroaryl group may be one in which one or more hydrogen atoms in the heteroaryl group are substituted with a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, an alkyl group, a cycloalkyl group, or the like. It is understood that the number of carbon atoms of the substituted heteroaryl refers to the total number of carbon atoms of the heteroaryl and substituents on the heteroaryl.
In the present application, the substituted or unsubstituted aryl group may have 6 to 25 carbon atoms, for example, 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25 carbon atoms.
Specific examples of the aryl group as a substituent in the present application include, but are not limited to, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, anthracyl,A base.
In the present application, the substituted or unsubstituted heteroaryl group may have 12 to 20 carbon atoms, for example, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms.
In the present application, specific examples of heteroaryl groups as substituents include, but are not limited to, triazinyl, pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothienyl, quinolinyl, quinazolinyl, quinoxalinyl, isoquinolinyl, carbazolyl, N-phenylcarbazolyl.
In the present application, the non-positive connection is referred to as a single bond extending from the ring systemIt means that one end of the bond can be attached to any position in the ring system through which the bond extends, and the other end is attached to the remainder of the compound molecule.
In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms of the alkyl group may be, for example, 1,2, 3,4, 5, 6, 7, 8, 9,10, and specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3, 7-dimethyloctyl.
In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, iodine.
In the present application, the cycloalkyl group having 3 to 10 carbon atoms may have 3,4, 5, 6, 7, 8, or 10 carbon atoms, for example. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl.
For example, as shown in formula (f), the naphthyl group represented by formula (f) is attached to the other positions of the molecule via two non-positional linkages extending through the bicyclic ring, which means includes any of the possible linkages shown in formulas (f-1) -formula (f-10).
As another example, as shown in the following formula (X '), the dibenzofuranyl group represented by the formula (X') is linked to the other position of the molecule through an unoositioned linkage extending from the middle of one benzene ring, and the meaning represented by this linkage includes any possible linkage as shown in the formula (X '-1) -formula (X' -4).
In some embodiments of the present applicationIn embodiments, X 1 Is N, X 2 And X 3 C (H); or X 2 Is N, X 1 And X 3 C (H); x is X 3 Is N, X 1 And X 2 C (H).
In some embodiments of the present application, X 1 And X 2 Is N, X 3 C (H); or X 1 And X 3 Is N, X 2 C (H); or X 2 And X 3 Is N, X 1 C (H).
In some embodiments of the present application, X 1 、X 2 And X 3 Are all N.
In some embodiments of the present application, the organic compound has a structure represented by formula 1-A, formula 1-B, formula 1-C, or formula 1-D:
in some embodiments of the present application, ar 1 And Ar is a group 2 Each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, and a substituted or unsubstituted heteroaryl group having 12 to 20 carbon atoms.
Alternatively, ar 1 And Ar is a group 2 Each independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25 carbon atoms and substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms.
Alternatively, ar 1 And Ar is a group 2 The substituents in (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, alkyl with 1-5 carbon atoms, trimethylsilyl, trifluoromethyl or aryl with 6-12 carbon atoms;
optionally Ar 1 Any two adjacent substituents of (a) form a saturated or unsaturated 5-13 membered ring;
optionally Ar 2 Any two adjacent substituents of (a) form a saturated or unsaturated 5-13 membered ring.
In other embodiments of the present application, ar 1 And Ar is a group 2 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, and substituted or unsubstituted carbazolyl.
Alternatively, ar 1 And Ar is a group 2 Each of the substituents is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, t-butyl, trimethylsilyl, trifluoromethyl, phenyl, naphthyl or biphenyl.
Optionally in Ar 1 And Ar is a group 2 Any two adjacent substituents may form cyclohexaneCyclopentane processBenzene ring, naphthalene ring or fluorene ring->
In some embodiments of the present application, ar 1 And Ar is a group 2 Each independently selected from the group consisting of substituted or unsubstituted groups W, wherein unsubstituted groups W are selected from the group consisting of:
wherein the substituted group W has one or more substituents independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl or phenyl, and when the number of substituents is greater than 1, the substituents are the same or different.
Optionally, aAr is ground, ar 1 And Ar is a group 2 Each independently selected from the group consisting of:
in some embodiments, ar 1 And Ar is a group 2 Each independently selected from the following groups:
in some embodiments of the present application, ar 3 Selected from phenyl, mono-deuterated phenyl, di-deuterated phenyl, tri-deuterated phenyl, tetra-deuterated phenyl or penta-deuterated phenyl.
Specifically, ar 3 Selected from the group consisting of
L, L in some embodiments of the present application 1 And L 2 The same or different, each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 20 carbon atoms.
Optionally L, L 1 And L 2 The same or different, are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms.
Optionally L, L 1 And L 2 The substituents in (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms or phenyl.
Optionally L, L 1 And L 2 The same or different, each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms.
Further alternatively, L is selected from a single bond or a substituted or unsubstituted arylene group having 6 to 15 carbon atoms.
Optionally L, L 1 And L 2 The same or different is selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted anthrylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted fluorenylene or substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothienyl, and substituted or unsubstituted carbazolylene.
Optionally L, L 1 And L 2 The substituents in (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl.
Further alternatively, L is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted fluorenylene group.
Further alternatively, L 1 And L 2 The same or different are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted fluorenylene group, or a substituted or unsubstituted dibenzofuranylene group.
L, L in some embodiments of the present application 1 And L 2 The same or different are each independently selected from a single bond, a substituted or unsubstituted group Q; wherein the unsubstituted group Q is selected from the group consisting of:
wherein the substituted group Q has one or more than two substituents independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl, and when the number of the substituents is greater than 1, the substituents are the same or different.
Optionally L, L 1 And L 2 The same or different, each independently selected from the group consisting of single bonds or:
further alternatively, L is selected from a single bond or the following group:
further alternatively, L 1 And L 2 Each independently selected from a single bond or the following groups:
in some embodiments of the present application,each independently selected from the group consisting of:
in particular, the method comprises the steps of,each independently selected from the group consisting of:
in some embodiments of the present applicationIn embodiments, R 1 And R is 2 Each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, or phenyl.
In some embodiments of the present application, n 1 And n 2 The same or different are respectively and independently selected from 0 or 1.
Optionally, the organic compound is selected from the group consisting of the compounds as set forth in claim 11.
In a second aspect, the present application provides an electronic component comprising an anode and a cathode disposed opposite each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises an organic compound of the present application.
Optionally, the electronic component is an organic electroluminescent device.
In some embodiments of the present application, the electronic component is an organic electroluminescent device. As shown in fig. 1, the organic electroluminescent device may include an anode 100, a hole transport layer 320, an electron blocking layer 330, an organic light emitting layer 340, an electron transport layer 350, and a cathode 200, which are sequentially stacked.
In some embodiments of the present application, the organic electroluminescent device is a blue organic electroluminescent device.
Alternatively, the anode 100 includes an anode material that is optionally a material with a large work function that facilitates hole injection into the functional layer. Specific examples of the anode material include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metal and oxide such as ZnO: al or SnO 2 Sb; or conductive polymers such as poly (3-methylthiophene) and poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but not limited thereto. A transparent electrode including Indium Tin Oxide (ITO) as an anode is preferable.
Alternatively, hole transport layer 320 comprises one or more hole transport materials, which may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, as may be selected by those skilled in the art with reference to the prior art.
In one embodiment, hole transport layer 320 is PAPB.
Optionally, electron blocking layer 330 includes one or more electron blocking materials, which may be selected from carbazole polymers or other types of compounds, as not particularly limited in this application. For example, the material of the electron blocking layer 330 is selected from the group consisting of:
in some embodiments of the present application, electron blocking layer 330 is HT-17.
Optionally, a hole injection layer 310 may also be provided between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320. The hole injection layer 310 may be a benzidine derivative, a starburst arylamine compound, a phthalocyanine derivative, or other materials, which are not particularly limited in this application. The material of the hole injection layer 310 may be selected from, for example, the following compounds or any combination thereof;
in some embodiments of the present application, hole injection layer 310 is comprised of HI-01 and PAPB.
Alternatively, the organic light emitting layer 340 may be composed of a single light emitting layer material, and may also include a host material and a dopant material. Alternatively, the organic light emitting layer 340 is composed of a host material and a dopant material, and holes injected into the organic light emitting layer 340 and electrons injected into the organic light emitting layer 340 may be recombined at the organic light emitting layer 340 to form excitons, which transfer energy to the host material, which transfers energy to the dopant material, thereby enabling the dopant material to emit light.
The host material of the organic light emitting layer 340 may be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, which are not particularly limited in this application.
In some embodiments of the present application, the host material of the organic light emitting layer 340 is BH-01.
The guest material of the organic light emitting layer 340 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which are not particularly limited in this application. Guest materials are also known as doping materials or dopants. Fluorescent dopants and phosphorescent dopants can be classified according to the type of luminescence. For example, specific examples of the blue fluorescent dopant include, but are not limited to:
in some embodiments of the present application, the guest material of the organic light emitting layer 340 is BD-01.
The electron transport layer 350 may be a single layer structure or a multi-layer structure, and may include one or more electron transport materials selected from but not limited to ET-1, liQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, and the comparison of the present application is not particularly limited. The materials of the electron transport layer 350 include, but are not limited to, the following compounds:
in some embodiments of the present application, electron transport layer 350 is comprised of an organic compound of the present application and LiQ.
In this application, cathode 200 may include a cathode materialWhich is a material with a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or a multi-layer material such as LiF/Al, liq/Al, liO 2 Al, liF/Ca, liF/Al and BaF 2 and/Ca. Optionally, a metal electrode comprising magnesium and silver is included as a cathode.
Optionally, an electron injection layer 360 may also be provided between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 360 may include an inorganic material such as an alkali metal sulfide, an alkali metal halide, or may include a complex of an alkali metal and an organic substance. In some embodiments of the present application, the electron injection layer 360 may include ytterbium (Yb).
A third aspect of the present application provides an electronic device comprising an electronic component as described in the second aspect of the present application.
According to one embodiment, as shown in fig. 2, an electronic device 400 is provided, which includes the organic electroluminescent device described above. The electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other type of electronic device, which may include, for example, but is not limited to, a computer screen, a cell phone screen, a television, an electronic paper, an emergency light, an optical module, etc.
The synthetic method of the organic compound of the present application is specifically described below with reference to synthetic examples, but the present application is not limited thereto.
All compounds of the synthetic methods not mentioned in the present application are commercially available starting products.
Synthetic examples
1. Synthesis of intermediates
1. Synthesis of intermediate IM a1-dX
Taking IM a1-d1 as an example, the synthesis of IM a1-dX is described:
(1) 5-hydroxy-2-adamantanone (25.00 g,150.40 mmol) was reacted with deuterated benzene (250 mL), trifluoromethanesulfonic acid (22.57 g,150.40 mmol) in a 150mL round bottom flask, and warmed to 80℃for 3h; the reaction solution was cooled to room temperature, washed with water to neutrality a plurality of times, separated into an organic phase, dried over anhydrous magnesium sulfate, filtered, and then the solvent was removed from the organic phase under reduced pressure to obtain a crude product, which was then crystallized with dichloromethane/n-heptane to obtain 5-deuterated phenyl-2-adamantanone (22.10 g, yield 63.5%).
(2) 2-bromo-4-chloroiodobenzene (70.00 g,220.58 mmol), phenylboronic acid (26.89 g,220.58 mmol), potassium carbonate (60.97 g,441.15 mmol), tetrabutylammonium bromide (7.11 g,22.06 mmol), toluene (560 mL), ethanol (140 mL) and deionized water (140 mL) were added to a three-necked flask, stirred under nitrogen for 15min, tetrakis (triphenylphosphine) palladium (2.55 g,1.21 mmol) was added and warmed to 75-80℃and stirred for 26 h. The reaction solution was cooled to room temperature, washed with water several times to neutrality, separated, dried with anhydrous magnesium sulfate, filtered, the solvent was removed from the organic phase under reduced pressure, and recrystallized from dichloromethane/n-heptane to give IM a1-a1 (30.20 g, yield 51.2%) as a white solid.
(3) IM a1-a1 (28.0 g,104.65 mmol) and THF (168 mL) are added into a 500mL round bottom flask, the system is cooled to-90 ℃ to-78 ℃, n-butyllithium (2 mol/L;62.80mL,125.58 mmol) tetrahydrofuran solution is added dropwise, the reaction is carried out for 1h at-90 ℃ to-78 ℃, then 5-phenyl-2 adamantanone (23.69 g,104.65 mmol) is dissolved by THF (120 mL) and then slowly added dropwise into the reaction system for reaction for 1h at-78 ℃ to-90 ℃, and then the reaction temperature is naturally raised to room temperature and stirred for 6h; water (200 mL) was added to the reaction system to terminate the reaction, extraction was performed with ethyl acetate and water, followed by drying and filtration, and the organic layer was concentrated under reduced pressure to obtain a crude product, which was recrystallized from acetonitrile to obtain IM a1-b1 (24.8 g, yield 57.1%).
(4) IM a1-b1 (24.5 g,51.93 mmol) was added to a 500mL round bottom flask with acetic acid (200 mL), sulfuric acid (98 wt%,1 mL), the temperature was raised to 75℃for 3h, as the reaction proceeded, the system was cooled to room temperature after the reaction was completed, then filtration was performed, the filter cake was rinsed with water and ethanol multiple times to obtain crude product, and the crude product was crystallized with dichloromethane/n-heptane to obtain IM a1-c1 (21.2 g, yield 90.4%).
(5) IM a1-c1 (21.0 g,52.90 mmol), pinacol diboronate (13.43 g,45.89 mmol), tris (dibenzylideneacetone) dipalladium (0.48 g,0.53 mmol), 2-dicyclohexylphosphorus-2 ',4',6' -triisopropylbiphenyl (0.44 g,1.06 mmol), potassium acetate (10.38 g,105.80 mmol) and 1, 4-dioxane (210 mL) were added to a three-necked round bottom flask, heated to 80℃under nitrogen and stirred for 4h; cooling to room temperature, washing the reaction liquid with water, separating liquid, adding magnesium sulfate into an organic phase, drying, filtering, and removing the solvent from the filtrate under reduced pressure; the crude product was purified by recrystallization using a toluene system to give solid IM a1-d1 (19.2 g, yield 76.7%).
Referring to the synthesis of IM a1-d1, the other IM a1-dX listed in Table 1 was synthesized, except that raw material 1 was used in place of 2-bromo-4-chloroiodobenzene in step (2), raw material 2 was used in place of phenylboronic acid in step (2), raw material 3 was used in place of 5-phenyl-2 adamantanone in step (3) and 5-deuterated phenyl-2 adamantanone was the product in step (1), and the main raw materials used and the final step yields for synthesizing IM a1-dX were as shown in Table 1.
TABLE 1
2. Synthesis of intermediate IM a1-d-bX
The synthesis of IM a1-d-bX is illustrated with IM a1-d-b 1:
(1) IM a1-d1 (5.50 g,11.26 mmol), 4-chlorobromobenzene (2.16 g,11.26 mmol), potassium carbonate (3.11 g,22.52 mmol), tetrabutylammonium bromide (0.32 g,1.13 mmol), toluene (45 mL), ethanol (15 mL) and deionized water (15 mL) were added to a three-necked flask, stirred under nitrogen for 15min, then tetrakis (triphenylphosphine) palladium (0.13 g,0.11 mmol) was added and the temperature was raised to 75℃to 80℃and stirred for 6h; the reaction solution was cooled to room temperature, washed with water several times to neutrality, separated, dried with anhydrous magnesium sulfate, filtered, and then the solvent was removed from the organic phase under reduced pressure, and recrystallized from methylene chloride/n-heptane to give a white solid, i.e., IM a1-d-a1 (3.61 g, yield 67.9%).
(2) IM a1-d-a1 (3.5 g,7.40 mmol), pinacol biborate (1.88 g,7.40 mmol), tris (dibenzylideneacetone) dipalladium (0.07 g,0.07 mmol), 2-dicyclohexylphosphorus-2 ',4',6' -triisopropylbiphenyl (0.07 g,0.15 mmol), potassium acetate (1.45 g,14.80 mmol) and 1, 4-dioxane (40 mL) were added to a three-necked round bottom flask, heated to 80℃under nitrogen and stirred for 3.5h; cooling to room temperature, washing the reaction liquid with water, separating liquid, adding magnesium sulfate into an organic phase, drying, filtering, and removing the solvent from the filtrate under reduced pressure; the crude product was purified by recrystallization using a toluene system to give solid IM a1-d-b1 (2.95 g, yield 70.6%).
Other IM a1-d-bX was synthesized by referring to the synthesis method of IM a1-d-b1, except that starting material 4 was used in place of IM a1-d-a1 in step (1) and starting material 5 was used in place of 4-chlorobromobenzene, and the main starting materials used and the synthesized IM a1-d-bX and final yields are shown in Table 2.
TABLE 2
3. Synthesis of intermediate IM a1-X
Taking IM a1-1 as an illustration of the synthesis of IM a1-X
IM a1-d1 (13.00 g,26.61 mmol), cyanuric chloride (4.91 g,26.61 mmol), potassium carbonate (7.36 g,53.23 mmol), tetrabutylammonium bromide (0.86 g,2.66 mmol), toluene (104 mL), ethanol (26 mL) and deionized water (26 mL) were added to a three-necked flask, stirred under nitrogen for 15min, and then tetrakis (triphenylphosphine) palladium (0.31 g,0.27 mmol) was added and the temperature was raised to 75℃to 80℃and stirred for 5 hours; the reaction solution was cooled to room temperature, washed with water several times to neutrality, separated, dried with anhydrous magnesium sulfate, filtered, and the solvent was removed from the organic phase under reduced pressure, followed by recrystallization with dichloroethane/n-heptane to give IM a1-1 (8.1 g, yield 59.6%) as a white solid.
Other IM a1-X was synthesized with reference to the synthesis of IM a1-1, except that raw material 6 was used in place of IM a1-d1, raw material 7 was used in place of cyanuric chloride, raw material 6, raw materials 7 and IM a1-X and the yields thereof are shown in Table 3.
TABLE 3 Table 3
2. Synthesis of Compounds
Synthesis example 1: synthesis of Compound 1-1
(1) IM a1-1 (7.9 g,15.48 mmol), phenylboronic acid (1.89 g,15.48 mmol), potassium carbonate (4.28 g,30.95 mmol), tetrabutylammonium bromide (0.50 g,1.55 mmol), toluene (64 mL), ethanol (16 mL) and deionized water (16 mL) were added to a three-necked flask, stirred under nitrogen for 15min, then tetrakis (triphenylphosphine) palladium (0.18 g,0.15 mmol) was added and the temperature was raised to 75℃to 80℃and stirred for 8 hours; the reaction solution was cooled to room temperature, washed with water several times to neutrality, separated, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and then the solvent was removed under reduced pressure, and recrystallized from methylene chloride/n-heptane to give IM A1-A1 (5.2 g, yield 60.8%) as a white solid.
(2) IM A1-A1 (5.0 g,9.06 mmol), 1-naphthalene boric acid (1.56 g,9.06 mmol), potassium carbonate (2.50 g,18.11 mmol), tetrabutylammonium bromide (0.29 g,0.10 mmol), toluene (40 mL), ethanol (10 mL) and deionized water (10 mL) were added to a three-necked flask, stirred under nitrogen for 15min, and tetrakis (triphenylphosphine) palladium (0.10 g,0.09 mmol) was added and heated to 75℃to 80℃and stirred for 10 hours; the reaction solution was cooled to room temperature, washed with water to neutrality a plurality of times, separated, dried with anhydrous magnesium sulfate, filtered, and then the solvent was removed from the organic phase under reduced pressure, followed by beating with toluene to give compound 1-1 (3.70 g, yield 63.5%) as a white solid. Mass spectrometry: m/z=644.3 [ m+h] + 。
The compounds listed in Table 4 were synthesized by the method described with reference to Compound 1-1 except that IM a1-1 was replaced with raw material 8, phenylboronic acid was replaced with raw material 9, and 1-naphthylboronic acid was replaced with raw material 10, and the main raw materials used, the synthesized compounds, the yields thereof and the mass spectrum results are shown in Table 4.
TABLE 4 Table 4
Some intermediate and compound nuclear magnetic data are shown in table 5 below:
TABLE 5
Organic electroluminescent device preparation and evaluation:
the embodiment also provides an organic electroluminescent device, which comprises an anode, a cathode and an organic layer between the anode and the cathode, wherein the organic layer comprises the organic compound. Hereinafter, the organic electroluminescent device of the present application will be described in detail by way of examples. However, the following examples are merely examples of the present application, and are not limiting of the present application.
Example 1: preparation of blue organic electroluminescent device
The anode was prepared by the following procedure: the ITO/Ag/ITO thickness isIs cut into a size of 40mm by 0.7mm, and is prepared into an experimental substrate having a cathode, an anode and an insulating layer pattern by using a photolithography process, and ultraviolet ozone and O 2 ：N 2 The plasma was surface treated to increase the work function of the anode (experimental substrate) and to descum.
Co-evaporation was performed at a weight ratio of 2% to 98% on the experimental substrate anode vacuum evaporation HI-01:PAPB to formAnd vapor plating PAPB on the hole injection layer to form a layer having a thickness of +.>A hole transport layer HTL of (c).
Vacuum evaporating HT-17 on the hole transport layer to form a film with a thickness ofIs a barrier to electrons.
On the electron blocking layer, BH-01 and BD-01 are co-evaporated in a weight ratio of 97% to 3% to form a film with a thickness ofAn organic light emitting layer (EML, blue light emitting layer).
On the organic light-emitting layer, the compound 1-1 and LiQ are formed by vapor deposition at a vapor deposition rate ratio of 1:1A thick electron transport layer.
Vapor deposition of Yb on electron transport layer to form a thickness ofThen, magnesium Mg and silver Ag are evaporated on the electron injection layer in vacuum according to the evaporation rate ratio of 1:9 to form the electron injection layer EIL with the thickness of +.>Is provided.
Finally, the thickness of the vapor deposited on the cathode isAnd thus the organic light emitting device is completed. />
Examples 2 to 29
An organic electroluminescent device was prepared in the same manner as in example 1, except that in preparing the electron transport layer, the compounds 1-1 were replaced with the compounds shown in table 6, respectively.
Comparative examples 1 to 3:
an organic electroluminescent device was prepared in the same manner as in example 1, except that in preparing the electron transport layer, compound 1-1 was replaced with compound a, compound b, and compound c, respectively.
Wherein, in preparing the organic electroluminescent device, the structures of the respective materials used in the comparative example and the examples are as follows:
compound c
The blue organic electroluminescent devices prepared in examples 1 to 29 and comparative examples 1 to 3 were subjected to performance test, in particular, at 10A/cm 2 The photoelectric properties and lifetime data of the devices were analyzed under the conditions of (a) and the results are shown in table 6 below.
TABLE 6
Referring to the above table, examples 1 to 29, in which the organic compound of the present application was used as the electron transport layer, had an improvement in current efficiency of at least 10.8% and an improvement in lifetime of at least 11.1% as compared with comparative examples 1 to 3. Therefore, when the organic compound is used for preparing the organic electroluminescent device, the driving voltage of the device can be effectively reduced, and the service life of the device is prolonged.
The organic compound of the present application is formed by combining an aryl-substituted adamantane group with a triazine group, and generally, has excellent thermal stability for adamantane because of its excellent sublimation due to its large space and robustness, and has a stable chemical structure; while the aryl group substituted with the hydrogen on adamantane can saturate the substituted carbon, the stability is further enhanced, and the combination with the triazine group can significantly improve the device and the efficiency and the service life.
It will be understood by those of ordinary skill in the art that the foregoing embodiments are specific examples of implementing the present application and that various changes in form and details may be made therein without departing from the spirit and scope of the present application.
Claims (14)
1. An organic compound, characterized in that the organic compound has a structure as shown in formula 1:
Ar 3 is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms;
Ar 3 the substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano, alkyl group with 1-5 carbon atoms or phenyl group;
X 1 、X 2 and X 3 Represents a C (H) or N atom, and X 1 、X 2 And X 3 At least one of which is an N atom;
L、L 1 and L 2 The same or different, each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms;
Ar 1 and Ar is a group 2 The same or different, each independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms and substituted or unsubstituted heteroaryl groups having 5 to 30 carbon atoms;
L、L 1 、L 2 、Ar 1 and Ar is a group 2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, deuterated alkyl with 1-10 carbon atoms, trialkylsilyl with 3-12 carbon atoms, aryl with 6-20 carbon atoms, heteroaryl with 5-15 carbon atoms or cycloalkyl with 3-10 carbon atoms;
optionally in Ar 1 And Ar is a group 2 Any two adjacent substituents form a ring;
R 1 and R is 2 Identical or different, each independentlySelected from deuterium, halogen group, cyano, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, deuterated alkyl with 1-10 carbon atoms, aryl with 6-20 carbon atoms;
n 1 r represents 1 And is selected from 0, 1,2, 3 or 4; when n is 1 When the number is greater than 1, any two R 1 The same or different;
n 2 r represents 2 And is selected from 0, 1,2 or 3; when n is 2 When the number is greater than 1, any two R 2 The same or different.
2. The organic compound according to claim 1, wherein X 1 、X 2 And X 3 Are all N.
3. The organic compound according to claim 1, wherein Ar 1 And Ar is a group 2 The same or different, each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 12 to 20 carbon atoms;
alternatively, ar 1 And Ar is a group 2 The substituents in (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, alkyl with 1-5 carbon atoms, trimethylsilyl, trifluoromethyl or aryl with 6-12 carbon atoms;
optionally Ar 1 Any two adjacent substituents of (a) form a saturated or unsaturated 5-13 membered ring;
optionally Ar 2 Any two adjacent substituents of (a) form a saturated or unsaturated 5-13 membered ring.
4. The organic compound according to claim 1, wherein Ar 1 And Ar is a group 2 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, andsubstituted or unsubstituted pyrenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, or substituted or unsubstituted carbazolyl;
alternatively, ar 1 And Ar is a group 2 Is the same or different and is each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, trifluoromethyl, phenyl, naphthyl or biphenyl;
optionally in Ar 1 And Ar is a group 2 Any two adjacent substituents form a cyclopentane, cyclohexane, benzene or fluorene ring.
5. The organic compound according to claim 1, wherein Ar 3 Selected from phenyl, mono-deuterated phenyl, di-deuterated phenyl, tri-deuterated phenyl, tetra-deuterated phenyl or penta-deuterated phenyl.
6. The organic compound according to claim 1, wherein Ar 3 Selected from the group consisting of
7. The organic compound according to claim 1, wherein L, L 1 And L 2 The same or different, each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 12 to 20 carbon atoms;
optionally L, L 1 And L 2 The substituents in (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms or phenyl.
8. The organic compound according to claim 1, wherein L, L 1 And L 2 The same or different are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted anthracenylene groupA group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted carbazole group;
optionally L, L 1 And L 2 The substituents in (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl.
9. The organic compound according to claim 1, wherein,each independently selected from the group consisting of:
10. the organic compound according to claim 1, wherein R 1 And R is 2 Identical or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
11. The organic compound according to claim 1, wherein the organic compound is selected from the group consisting of:
12. an electronic component includes an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises the organic compound according to any one of claims 1 to 11;
optionally, the electronic component is an organic electroluminescent device.
13. The electronic component of claim 12, wherein the functional layer comprises an electron transport layer comprising the organic compound.
14. An electronic device comprising the electronic component of claim 12 or 13.
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| CN113717122B (en) * | 2021-09-17 | 2024-02-02 | 长春海谱润斯科技股份有限公司 | Adamantane spirofluorene derivative and organic electroluminescent device thereof |
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