CN116332945A - 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
- Publication number
- CN116332945A CN116332945A CN202210339773.7A CN202210339773A CN116332945A CN 116332945 A CN116332945 A CN 116332945A CN 202210339773 A CN202210339773 A CN 202210339773A CN 116332945 A CN116332945 A CN 116332945A
- Authority
- CN
- China
- Prior art keywords
- substituted
- carbon atoms
- group
- unsubstituted
- same
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims description 87
- 239000010410 layer Substances 0.000 claims description 78
- 125000003118 aryl group Chemical group 0.000 claims description 61
- 125000001424 substituent group Chemical group 0.000 claims description 39
- -1 dibenzofuranyl Chemical group 0.000 claims description 36
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 229910052805 deuterium Inorganic materials 0.000 claims description 29
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 239000011737 fluorine Substances 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
- 239000002346 layers by function Substances 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
- 125000000732 arylene group Chemical group 0.000 claims description 10
- 235000010290 biphenyl Nutrition 0.000 claims description 10
- 239000004305 biphenyl Substances 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000005549 heteroarylene group Chemical group 0.000 claims description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000005561 phenanthryl group Chemical group 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000005567 fluorenylene group Chemical group 0.000 claims description 5
- 125000004957 naphthylene group Chemical group 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
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 description 42
- 150000001875 compounds Chemical class 0.000 description 28
- 230000005525 hole transport Effects 0.000 description 19
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 18
- 239000000543 intermediate Substances 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000002347 injection Methods 0.000 description 15
- 239000007924 injection Substances 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 230000000903 blocking effect Effects 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 8
- 150000004982 aromatic amines Chemical group 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 229940125904 compound 1 Drugs 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
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 230000005684 electric field Effects 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 125000005259 triarylamine group Chemical group 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000000746 purification Methods 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
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- MKHDDTWHDFVYDQ-UHFFFAOYSA-N 2,4-dibromo-1-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1Br MKHDDTWHDFVYDQ-UHFFFAOYSA-N 0.000 description 2
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- XRHGYUZYPHTUJZ-UHFFFAOYSA-N 4-chlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1 XRHGYUZYPHTUJZ-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-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
- 230000009286 beneficial effect Effects 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
- 230000005540 biological transmission Effects 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000001975 deuterium Chemical group 0.000 description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 2
- 239000003480 eluent 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
- 125000005842 heteroatom Chemical group 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
- 150000002739 metals Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 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 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 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
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000001308 synthesis method Methods 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
- 239000011787 zinc oxide Substances 0.000 description 2
- 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 1
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 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
- 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
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-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
- 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
- 239000002585 base Substances 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
- 230000008033 biological extinction Effects 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
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001716 carbazoles Chemical group 0.000 description 1
- 125000005566 carbazolylene group Chemical group 0.000 description 1
- 238000012512 characterization method Methods 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
- 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
- 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
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 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
- 230000000694 effects Effects 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
- 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
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
- 229960005544 indolocarbazole Drugs 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
- 230000031700 light absorption Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 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
- 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
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl 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
- 239000004065 semiconductor Substances 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
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005649 substituted arylene group Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 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
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 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
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/16—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H10K50/155—Hole transporting layers comprising dopants
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
-
- 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)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (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 progress of material science, the research scope of electroluminescent or photoelectric conversion electronic components is becoming wider and wider. The organic electroluminescent device is also called an organic light emitting diode, and refers to a phenomenon that an organic luminescent material emits light when excited by current under the action of an electric field. 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. Taking an organic electroluminescent device as an example, 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.
The organic charge transport material is an organic semiconductor material which can realize the directional ordered controllable migration of carriers under the action of an electric field when carriers (electrons or holes) are injected, thereby achieving the purpose of transporting charges. Such materials require excellent electron donating properties, lower ionization potential, high hole mobility, good solubility and amorphous film forming properties, stronger fluorescent properties and photostability. Currently, the hole transport layer materials are mainly poly-p-phenylenevinylenes, triarylamines, hydrazones, butadienes and the like. The superior performance of triarylamine materials is one of the hot spots of research, and the prior art discloses materials capable of preparing a hole transport layer in an organic electroluminescent device. However, the existing triarylamine hole transport layer material has poor performance in terms of voltage, luminous efficiency, power and service life in devices, and has a very large improvement and promotion space. Accordingly, there remains a need 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, and an electronic component and an electronic device including the same, which can improve the performance of the electronic component and the electronic device, such as reducing the driving voltage of a device, improving the efficiency and the lifetime of the device.
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:
wherein each R 1 、R 2 、R 3 And R is 4 The two groups are identical or different and are respectively and independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1-10 carbon atoms, aryl groups with 6-20 carbon atoms and heteroaryl groups with 5-20 carbon atoms;
R 5 、R 6 、R 7 and R is 8 Independently selected from hydrogen or a structure represented by formula 1-1, and R 5 、R 6 、R 7 And R is 8 At least one selected from the structures shown in formula 1-1;
L、L 1 and L 2 The same or different, are respectively and independently selected from single bond, substituted or unsubstituted arylene with 6-30 carbon atoms and substituted or unsubstituted heteroarylene with 3-30 carbon atoms;
Ar 1 a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
Ar 2 selected from the group represented by formulas 1-2;
x is selected from C (R) 11 R 12 ) O or S;
each R is 9 And R is 10 The same or different, are respectively and independently selected from deuterium, halogen group, cyano, alkyl with 1-10 carbon atoms or aryl with 6-12 carbon atoms;
R 11 and R is 12 The same or different are respectively and independently selected from alkyl with 1-10 carbon atoms or aryl with 6-12 carbon atoms;
n 1 is R 1 Is selected from 0, 1,2, 3 or 4, when n 1 When the number is greater than 1, any two R 1 The same or different;
n 2 is R 2 Is selected from 0, 1,2, 3 or 4, when n 2 When the number is greater than 1, any two R 1 The same or different;
n 3 is R 3 Is selected from 0, 1 or 2, when n 3 When the number is greater than 1, any two R 3 The same or different;
n 4 is R 4 Is selected from 0, 1,2, 3 or 4, when n 4 When the number is greater than 1, any two R 4 The same or different;
n 9 is R 9 Is selected from 0, 1,2 or 3, when n 9 When the number is greater than 1, any two R 9 The same or different;
n 10 is R 10 Is selected from 0, 1,2, 3 or 4, when n 10 When the number is greater than 1, any two R 10 The same or different;
said L, L 1 、L 2 And Ar is a group 1 The substituents in (a) are the same or different and are respectively and independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1-10 carbon atoms, cycloalkyl groups with 3-10 carbon atoms, aryl groups with 6-20 carbon atoms or heteroaryl groups with 5-20 carbon atoms;
optionally Ar 1 Any two adjacent substituents of (a) form a ring.
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 aromatic amine group is connected with a special large-plane conjugated group and a dibenzofive-membered ring group by the organic compound, wherein the special conjugated group used by the organic compound has a higher T1 value, and is beneficial to carrier and energy transmission. This mode of attachment of the present application allows the compound molecule to have high HOMO orbital coverage and strong polarity, thus having good hole mobility. The organic compound can effectively avoid intermolecular stacking, and improves the film forming property of the compound. When the organic compound is used as a hole transport layer material of the organic electroluminescent device, the working voltage of the device can be obviously reduced, and the efficiency and the service life of the device are improved.
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:
wherein each ofR 1 、R 2 、R 3 And R is 4 The two groups are identical or different and are respectively and independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1-10 carbon atoms, aryl groups with 6-20 carbon atoms and heteroaryl groups with 5-20 carbon atoms;
R 5 、R 6 、R 7 and R is 8 Independently selected from hydrogen or a structure represented by formula 1-1, and R 5 、R 6 、R 7 And R is 8 At least one selected from the structures shown in formula 1-1;
L、L 1 and L 2 The same or different, are respectively and independently selected from single bond, substituted or unsubstituted arylene with 6-30 carbon atoms and substituted or unsubstituted heteroarylene with 3-30 carbon atoms;
Ar 1 a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
Ar 2 selected from the group represented by formulas 1-2;
x is selected from C (R) 11 R 12 ) O or S;
each R is 9 And R is 10 The same or different, are respectively and independently selected from deuterium, halogen group, cyano, alkyl with 1-10 carbon atoms or aryl with 6-12 carbon atoms;
R 11 and R is 12 The same or different are respectively and independently selected from alkyl with 1-10 carbon atoms or aryl with 6-12 carbon atoms;
n 1 is R 1 Is selected from 0, 1,2, 3 or 4, when n 1 When the number is greater than 1, any two R 1 The same or different;
n 2 is R 2 Is selected from 0, 1,2, 3 or 4, when n 2 When the number is greater than 1, any two R 1 The same or different;
n 3 is R 3 Is selected from 0, 1 or 2;
n 4 is R 4 Is selected from 0, 1,2, 3 or 4, when n 4 When the number is greater than 1, any two R 4 The same or different;
n 9 is R 9 Is selected from 0, 1,2 or 3, when n 9 When the number is greater than 1, any two R 9 The same or different;
n 10 is R 10 Is selected from 0, 1,2, 3 or 4, when n 10 When the number is greater than 1, any two R 10 The same or different;
said L, L 1 、L 2 、Ar 1 The substituents in (a) are the same or different and are respectively and independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1-10 carbon atoms, cycloalkyl groups with 3-10 carbon atoms, aryl groups with 6-20 carbon atoms or heteroaryl groups with 5-20 carbon atoms;
optionally Ar 1 Any two adjacent substituents of (a) form a ring.
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 R' substituent groups on two benzene rings can be the same or different, each R 'can be the same or different, and each R' has the option ofThe two are not mutually influenced.
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, cycloalkyl or the like.
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 hetero atoms such as B, N, O, S, P, se, si and the like. 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 5 to 20 carbon atoms, for example, 5, 6, 7, 8, 9,10, 11, 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 system
It 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, and the like.
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 application, R 5 、R 6 、R 7 And R is 8 And only one selected from the structures shown in formula 1-1.
In some embodiments of the present application, the organic compound has a structure represented by formula 1-a:
in some embodiments of the present application, ar 1 Selected from the group consisting ofA substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 20 carbon atoms.
Alternatively, ar 1 A substituted or unsubstituted aryl group selected from the group consisting of 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25 and a substituted or unsubstituted heteroaryl group having 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms.
Alternatively, ar 1 Each substituent of (a) is independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, or aryl having 6 to 12 carbon atoms.
Optionally in Ar 1 Any two adjacent substituents may form cyclohexane
Cyclopentane process
Benzene ring, naphthalene ring or fluorene ring->
Optionally Ar 1 Any two adjacent substituents of the formula (I) form a saturated or unsaturated ring with the carbon number of 5-13.
Specifically, ar 1 Specific examples of substituents in (a) include, but are not limited to: deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, phenyl, naphthyl or biphenyl.
In other embodiments of the present application, ar 1 Selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted terphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, and substituted or unsubstituted spirobifluorenyl.
Alternatively, ar 1 Each of the substituents in (a) is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, naphthyl or biphenyl.
In some embodiments of the present application, ar 1 Selected from a substituted or unsubstituted group W, wherein the unsubstituted group W is selected from the following groups:
wherein the substituted group W has one or more substituents independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, dibenzofuranyl or dibenzothiophenyl, and when the number of substituents is greater than 1, the substituents are the same or different.
Alternatively, ar 1 Selected from the group consisting of:
in some embodiments, ar 1 Selected from the following groups:
in some embodiments of the present application, n 1 、n 2 、n 3 And n 4 All 0.
In some embodiments of the present application, each R 1 、R 2 、R 3 And R is 4 Each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, or phenyl.
In some embodiments of the present application, n 9 And n 10 All 0.
In some embodiments of the present application, each R 9 And R is 10 Each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, or phenyl.
In some embodiments of the present application, X is selected from C (R 11 R 12 ) And R is 11 And R is 12 Are all methyl groups.
In some embodiments of the present application, X is selected from O or S.
In some embodiments of the present application, ar 2 Selected from the group consisting of:
each R is 9 And R is 10 Each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, or phenyl.
In some embodiments of the present application, ar 2 Selected from the group consisting of:
in some embodiments of the present application, ar 2 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 5 to 20 carbon atoms.
Optionally L, L 1 And L 2 Identical or different, each independentlyThe standing is selected from single bond, substituted or unsubstituted arylene groups with carbon atoms of 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, and substituted or unsubstituted heteroarylene groups with carbon atoms of 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20.
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.
Alternatively, L 1 And L 2 The same or different are respectively and independently selected from single bond, substituted or unsubstituted arylene with 6-15 carbon atoms.
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 phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, and 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, cyclohexyl or phenyl.
Alternatively, L is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group.
Alternatively, L is selected from the group consisting of substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, and substituted or unsubstituted carbazolylene.
When L is not a single bond, namely, the nitrogen-containing group of the organic compound is connected with the aromatic amine through aryl or heteroaryl, the material has a deeper HOMO energy level, and is beneficial to hole injection and transmission.
Alternatively, L 1 Selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group.
Alternatively, L 2 Selected from single bond, substituted or unsubstituted phenylene.
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, phenyl, naphthyl or biphenyl, 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 Independently selected from a single bond or the following groups:
further alternatively, L 2 Selected from single bonds or
Alternatively, the organic compound is selected from the group of compounds as shown in claim 10.
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. Preferred bagIncludes Indium Tin Oxide (ITO) as the transparent electrode of the anode.
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 an organic compound as described herein.
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-16.
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 F4-TCNQ.
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 BCP and LiQ.
In this application, the cathode 200 may include a cathode material, which is a material having 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 aX
Synthesis of a1
Indolocarbazole (50.0 g;195.1 mmol), 2, 4-dibromo-1-fluorobenzene (41.3 g;162.6 mmol), cesium carbonate (105.9 g;325.1 mmol), N, N-dimethylformamide (500 mL) were added to a round-bottomed flask, and the mixture was stirred and heated to 150℃to 153℃under nitrogen protection for 12 hours. The reaction mixture was cooled to room temperature, washed with water, and the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; the crude product was purified by silica gel column chromatography using methylene chloride/n-heptane as an eluent, followed by recrystallization purification using toluene/n-heptane to give intermediate a1 (38.6 g; yield 58%) as a white solid.
Referring to the synthesis of intermediate a1, reactant a in table 1 was substituted for 2, 4-dibromo-1-fluorobenzene to synthesize intermediate a2 shown in table 1. The main raw materials used, the synthesized intermediates and the yields thereof are shown in Table 1.
TABLE 1
2. Synthesis of intermediate a1-X
Synthesis of intermediate a1-1
Intermediate a1 (25 g;61.1 mmol), 4-chlorobenzeneboronic acid (11.5 g;73.3 mmol), tetrakis (triphenylphosphine) palladium (0.7 g;0.6 mmol), potassium carbonate (16.9 g;122.2 mmol), tetrabutylammonium bromide (2.0 g;6.1 mmol), toluene (200 mL), ethanol (100 mL) and deionized water (50 mL) were added to a round bottom flask and heated to 75℃to 80℃with stirring under nitrogen protection for 12 hours. The reaction mixture was cooled to room temperature, washed with water, and the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; the crude product was purified by silica gel column chromatography using methylene chloride/n-heptane as an eluent, followed by recrystallization purification using toluene/n-heptane to give intermediate a1-1 (20.2 g; yield 75%) as a white solid.
Referring to the synthesis method of the intermediate a1-1, the intermediate shown in Table 2 was synthesized by substituting reactant B in Table 2 for 4-chlorobenzoic acid. The main raw materials used, the synthesized intermediates and the yields thereof are shown in Table 2.
TABLE 2
Referring to the synthesis method of intermediate a1-1, intermediate a2 was substituted for a1, and reactant C in table 3 was substituted for 4-chlorobenzoic acid to synthesize the intermediates shown in table 3. The main raw materials used, the synthesized intermediates and the yields thereof are shown in Table 3.
TABLE 3 Table 3
3. Synthesis of Compounds
Synthesis of Compound 1
Intermediate a1 (10 g;24.4 mmol), N-phenyl-3-dibenzofuran-2-amine (5.8 g;22.2 mmol), tris (dibenzylideneacetone) dipalladium (0.2 g;0.2 mmol), 2-dicyclohexylphosphorus-2, 6-dimethoxybiphenyl (0.2 g;0.4 mmol), sodium tert-butoxide (3.2 g;33.3 mmol) and toluene (200 mL) were added to a nitrogen-protected round-bottomed flask and the mixture was allowed to warm to 105℃to 110℃with stirring for 16 hours; the reaction solution was cooled to room temperature, the organic phase was separated after washing with water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; the obtained crude product was purified by silica gel column chromatography using methylene chloride/n-heptane, followed by recrystallization purification using toluene/n-heptane to obtain compound 1 (9.8 g; yield 75%) as a white solid.
Synthesis examples 2 to 13:
referring to the synthesis of compound 1, the compounds of table 4 were synthesized using reactant D of table 4 instead of N-phenyl-3-dibenzofuran-2-amine. The main raw materials used, the synthesized compounds and the final yields thereof are shown in Table 4.
TABLE 4 Table 4
Synthesis examples 14 to 39:
referring to the synthesis of compound 1, the compounds of table 5 were synthesized using reactant E in table 5 instead of intermediate a1 and reactant F instead of N-phenyl-3-dibenzofuran-2-amine. The main raw materials used, the synthesized compounds and the final yields thereof are shown in Table 5.
TABLE 5
Compound characterization data:
the compound profile data are shown in table 6 below:
TABLE 6
Some intermediate and compound nuclear magnetic data are shown in table 7 below:
TABLE 7
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: will be of the thickness of
The ITO substrate (manufactured by Corning) was cut into a size of 40 mm. Times.40 mm. Times.0.7 mm, and a test substrate having a cathode, an anode and an insulating layer pattern was prepared by a photolithography step, and an ultraviolet ozone and O were used 2 ：N 2 The plasma was surface treated to increase the work function of the anode (experimental substrate) and to descum.
Vacuum deposition of F4-TCNQ on an experimental substrate (anode) to form a thickness of
Is formed by vapor deposition of compound 1 on the hole injection layer to a thickness of +.>
A Hole Transport Layer (HTL).
Vacuum evaporating HT-16 on the hole transport layer to form a film with a thickness of
Electron Blocking Layer (EBL).
On the electron blocking layer, BD-01 doped with BH-01 (film thickness ratio) was co-evaporated to form a film having a thickness of
An organic light emitting layer (blue light emitting layer, B-EML).
On the organic light emitting layer, BCP and LiQ are formed by vapor deposition in a weight ratio of 1:1
A thick Electron Transport Layer (ETL).
Vapor deposition of Yb on electron transport layer to form a thickness of
Then vacuum evaporating magnesium and silver on the electron injection layer at an evaporation rate of 1:10 to form a film having a thickness +.>
Is provided.
In addition, the thickness of the vapor deposited on the cathode is
And forming an organic capping layer (CPL), thereby completing the manufacture of the organic light emitting device.
Example 2-example 39:
an organic electroluminescent device was prepared in the same manner as in example 1, except that in preparing a hole transport layer, compound 1 was replaced with the compound shown in table 8, respectively.
Comparative example 1-comparative example 4:
an organic electroluminescent device was prepared in the same manner as in example 1, except that in preparing the hole transport layer, compound 1 was replaced with compound a, compound B, compound C, and compound D, 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:
the blue organic electroluminescent devices prepared in examples 1 to 39 and comparative examples 1 to 4 were subjected to performance test, particularly at 20mA/cm 2 The photoelectric properties of the devices were tested under the conditions shown in table 8.
TABLE 8
Referring to the above table, when the compounds of examples 1 to 39 were used as the hole transport layer material, the current efficiency was improved by at least 10.7% and the lifetime was improved by at least 12% as compared with comparative examples 1 to 4.
The compounds of the present application all have improved device performance compared to comparative examples 1-4. Compared with comparative example 1, the organic compound has the advantages that the aromatic amine group is used for connecting a special nitrogen-containing group and a dibenzofive-membered ring, so that the hole mobility of compound molecules can be greatly improved, the voltage of a device can be reduced, and the luminous efficiency can be improved.
Compared with comparative examples 2-4, the compound has relatively suitable energy band width and ultraviolet-visible light absorption range, and can reduce extinction effect and improve efficiency when being used as a hole transport layer.
Therefore, the organic compound can effectively improve the luminous efficiency of the organic electroluminescent device and prolong the service life of the organic electroluminescent device when being used for preparing the blue organic electroluminescent device. The device lifetime enhancement is more pronounced especially when the nitrogen-containing groups of the organic compounds of the present application are linked to the aromatic amine via an aryl or heteroaryl group. The reason for this may be that when the nitrogen-containing group of the organic compound of the present application is linked to an aromatic amine via an aryl or heteroaryl group, the material has a deeper HOMO level, which is advantageous for hole injection and transport.
Therefore, when the organic compound is used for preparing the organic electroluminescent device, the driving voltage of the device can be effectively reduced, and meanwhile, the efficiency and the service life of the device are improved.
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 (13)
1. An organic compound, characterized in that the organic compound has a structure represented by formula 1:
wherein each R 1 、R 2 、R 3 And R is 4 The two groups are identical or different and are respectively and independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1-10 carbon atoms, aryl groups with 6-20 carbon atoms and heteroaryl groups with 5-20 carbon atoms;
R 5 、R 6 、R 7 and R is 8 Independently selected from hydrogen or a structure represented by formula 1-1, and R 5 、R 6 、R 7 And R is 8 At least one selected from the structures shown in formula 1-1;
L、L 1 and L 2 The same or different, are respectively and independently selected from single bond, substituted or unsubstituted arylene with 6-30 carbon atoms and substituted or unsubstituted heteroarylene with 3-30 carbon atoms;
Ar 1 a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
Ar 2 selected from the group represented by formulas 1-2;
x is selected from C (R) 11 R 12 ) O or S;
each R is 9 And R is 10 The same or different, are respectively and independently selected from deuterium, halogen group, cyano, alkyl with 1-10 carbon atoms or aryl with 6-12 carbon atoms;
R 11 and R is 12 The same or different are respectively and independently selected from alkyl with 1-10 carbon atoms or aryl with 6-12 carbon atoms;
n 1 is R 1 Is selected from 0, 1,2, 3 or 4, when n 1 When the number is greater than 1, any two R 1 The same or different;
n 2 is R 2 Is selected from 0, 1,2, 3 or 4, when n 2 When the number is greater than 1, any two R 1 The same or different;
n 3 is R 3 Is selected from 0, 1 or 2, when n 3 When the number is greater than 1, any two R 3 The same or different;
n 4 is R 4 Is selected from 0, 1,2, 3 or 4, when n 4 When the number is greater than 1, any two R 4 The same or different;
n 9 is R 9 Is selected from 0, 1,2 or 3, when n 9 When the number is greater than 1, any two R 9 The same or different;
n 10 is R 10 Is selected from 0, 1,2, 3 or 4, when n 10 When the number is greater than 1, any two R 10 The same or different;
said L, L 1 、L 2 And Ar is a group 1 The substituents in (a) are the same or different and are respectively and independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1-10 carbon atoms, cycloalkyl groups with 3-10 carbon atoms, aryl groups with 6-20 carbon atoms or heteroaryl groups with 5-20 carbon atoms;
optionally Ar 1 Any two adjacent substituents of (a) form a ring.
2. The organic compound according to claim 1, wherein the organic compound has a structure represented by formula 1-a:
3. the organic compound according to claim 1, wherein Ar 1 A substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 20 carbon atoms;
alternatively, ar 1 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, cycloalkyl having 5 to 10 carbon atoms or aryl having 6 to 12 carbon atoms;
optionally Ar 1 Any two adjacent substituents of the formula (I) form a saturated or unsaturated ring with the carbon number of 5-13.
4. The organic compound according to claim 1, wherein Ar 1 Selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted terphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, and substituted or unsubstituted spirobifluorenyl;
alternatively, ar 1 The substituents of (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, naphthyl or biphenyl.
5. The organic compound according to claim 1, wherein the Ar 2 Selected from the group consisting of:
each R is 9 And R is 10 Each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, or phenyl.
6. The organic compound according to claim 1, wherein theAr is as described in 2 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 5 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, each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophene 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, cyclohexyl or phenyl.
9. The organic compound according to claim 1, wherein each R 1 、R 2 、R 3 And R is 4 The same or different are respectively and independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tertiary butyl, cyclohexyl or phenyl.
10. The organic compound according to claim 1, wherein the organic compound is selected from the group consisting of:
11. 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 of any one of claims 1-10;
optionally, the electronic component is an organic electroluminescent device.
12. The electronic element according to claim 11, wherein the functional layer includes a hole-transporting layer, the hole-transporting layer containing the organic compound.
13. An electronic device comprising the electronic component of claim 11 or 12.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210339773.7A CN116332945A (en) | 2022-04-01 | 2022-04-01 | Organic compound, and electronic component and electronic device including the same |
| PCT/CN2022/135028 WO2023185039A1 (en) | 2022-04-01 | 2022-11-29 | Organic compound, and electronic element and electronic apparatus comprising same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210339773.7A CN116332945A (en) | 2022-04-01 | 2022-04-01 | Organic compound, and electronic component and electronic device including the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116332945A true CN116332945A (en) | 2023-06-27 |
Family
ID=86877881
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210339773.7A Pending CN116332945A (en) | 2022-04-01 | 2022-04-01 | Organic compound, and electronic component and electronic device including the same |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN116332945A (en) |
| WO (1) | WO2023185039A1 (en) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20210046295A (en) * | 2019-10-18 | 2021-04-28 | 솔브레인 주식회사 | The thermally activated delayed fluorescence dopant material and organic light emitting diode comprising the same |
| KR20210046294A (en) * | 2019-10-18 | 2021-04-28 | 솔브레인 주식회사 | The thermally activated delayed fluorescence dopant material and organic light emitting diode comprising the same |
| KR102586097B1 (en) * | 2020-04-20 | 2023-10-05 | 삼성에스디아이 주식회사 | Compound for organic optoelectronic device, organic optoelectronic device and display device |
-
2022
- 2022-04-01 CN CN202210339773.7A patent/CN116332945A/en active Pending
- 2022-11-29 WO PCT/CN2022/135028 patent/WO2023185039A1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2023185039A1 (en) | 2023-10-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN114133332B (en) | Organic compound, electronic component, and electronic device | |
| CN113582997B (en) | Nitrogen-containing compound, electronic component and electronic device | |
| CN113214280B (en) | Organic compound, and electronic device and electronic apparatus including the same | |
| CN115557937B (en) | Nitrogen-containing compound, organic electroluminescent device and electronic device comprising same | |
| CN115650899B (en) | Nitrogen-containing compound, electronic component and electronic device | |
| CN115385898B (en) | Nitrogen-containing compound, organic electroluminescent device and electronic device | |
| CN115521212B (en) | Organic material, electronic element and electronic device | |
| CN113896720B (en) | Organic compound, electronic component, and electronic device | |
| CN114133351B (en) | Nitrogen-containing compound, and electronic component and electronic device comprising same | |
| CN116396280A (en) | Organic compound, organic electroluminescent device and electronic apparatus | |
| CN115521214B (en) | Organic compound, and electronic component and electronic device including the same | |
| CN115490601B (en) | Organic compound, electronic component, and electronic device | |
| CN114335399B (en) | Organic electroluminescent device and electronic device including the same | |
| WO2023185039A1 (en) | Organic compound, and electronic element and electronic apparatus comprising same | |
| CN115490603B (en) | Organic compound, and electronic component and electronic device including the same | |
| CN114181166B (en) | Organic compound, and electronic component and electronic device including the same | |
| CN114426539B (en) | Organic compound, organic electroluminescent device and electronic device comprising the same | |
| CN114989179B (en) | Organic compound, organic electroluminescent device using the same, and electronic device | |
| CN114075214B (en) | Organic compound, organic electroluminescent device and electronic device comprising the same | |
| CN116444384A (en) | Organic compound, organic electroluminescent device and electronic apparatus | |
| CN116478115A (en) | Organic compound, organic electroluminescent device and electronic apparatus | |
| CN117897030A (en) | Organic electroluminescent device and electronic device | |
| CN117720545A (en) | Nitrogen-containing compound, organic electroluminescent device and electronic device | |
| CN117417260A (en) | Organic material, organic electroluminescent device and electronic device | |
| CN117603192A (en) | Organic compound, composition, organic electroluminescent device, and electronic device |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |