CN115521212A - Organic material, electronic component, and electronic device - Google Patents
Organic material, electronic component, and electronic device Download PDFInfo
- Publication number
- CN115521212A CN115521212A CN202210407500.1A CN202210407500A CN115521212A CN 115521212 A CN115521212 A CN 115521212A CN 202210407500 A CN202210407500 A CN 202210407500A CN 115521212 A CN115521212 A CN 115521212A
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- 239000011368 organic material Substances 0.000 title claims abstract description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 110
- 125000003118 aryl group Chemical group 0.000 claims description 82
- 239000010410 layer Substances 0.000 claims description 71
- 125000001424 substituent group Chemical group 0.000 claims description 65
- -1 dibenzofuranyl group Chemical group 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 28
- 229910052805 deuterium Inorganic materials 0.000 claims description 26
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 25
- 125000001072 heteroaryl group Chemical group 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 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 239000002346 layers by function Substances 0.000 claims description 14
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000001624 naphthyl group Chemical group 0.000 claims description 11
- 125000000732 arylene group Chemical group 0.000 claims description 9
- 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
- 125000005561 phenanthryl 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
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- 239000004305 biphenyl Substances 0.000 claims description 8
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 8
- 125000005549 heteroarylene group Chemical group 0.000 claims description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000005106 triarylsilyl group Chemical group 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 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 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 125000006267 biphenyl group Chemical group 0.000 claims description 3
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 3
- 125000004653 anthracenylene group Chemical group 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 125000005567 fluorenylene group Chemical group 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000005562 phenanthrylene group Chemical group 0.000 claims description 2
- BZLZKLMROPIZSR-UHFFFAOYSA-N triphenylsilicon Chemical group C1=CC=CC=C1[Si](C=1C=CC=CC=1)C1=CC=CC=C1 BZLZKLMROPIZSR-UHFFFAOYSA-N 0.000 claims description 2
- 239000000463 material Substances 0.000 description 42
- 230000005525 hole transport Effects 0.000 description 15
- 239000000543 intermediate Substances 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000002347 injection Methods 0.000 description 12
- 239000007924 injection Substances 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- 125000005259 triarylamine group Chemical group 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
- 230000021615 conjugation Effects 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- 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
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000005684 electric field Effects 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000002035 prolonged effect Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-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
- 230000009471 action Effects 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 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
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-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
- 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 238000010549 co-Evaporation Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 125000005956 isoquinolyl group Chemical group 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000002894 organic compounds Chemical class 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
- 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 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
- 125000005493 quinolyl group Chemical group 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
- 238000006467 substitution reaction Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 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
- JAUCIDPGGHZXRP-UHFFFAOYSA-N 4-phenyl-n-(4-phenylphenyl)aniline Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1NC(C=C1)=CC=C1C1=CC=CC=C1 JAUCIDPGGHZXRP-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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-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
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 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
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 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
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 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
- 238000012512 characterization method Methods 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 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
- 238000000151 deposition Methods 0.000 description 1
- 150000001975 deuterium Chemical group 0.000 description 1
- 125000004431 deuterium atom 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
- 125000004212 difluorophenyl group Chemical group 0.000 description 1
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 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
- 238000001704 evaporation Methods 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
- 239000011521 glass Substances 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
- 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
- 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
- 238000004519 manufacturing process 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
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification 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
- 239000012044 organic layer 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
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 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
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 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
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005649 substituted arylene group Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 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
- 125000004587 thienothienyl group Chemical group S1C(=CC2=C1C=CS2)* 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
- 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
- 125000004360 trifluorophenyl group Chemical group 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 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
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- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
- C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C07D333/76—Dibenzothiophenes
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- 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
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- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
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Abstract
The present application relates to an organic material, an electronic element, and an electronic device. The organic material has a structure shown as formula 1, and the organic material is prepared byWhen the organic electroluminescent device is used in an organic electroluminescent device, the performance of the device can be remarkably improved.
Description
Technical Field
The present application belongs to the technical field of organic materials, and in particular, to an organic material, and an electronic device and an electronic component including the same.
Background
With the development of electronic technology and the advancement of material science, the research range of electronic components for electroluminescence or photoelectric conversion is more and more extensive. Among them, the organic electroluminescent device is also called as an organic light emitting diode, which refers to a phenomenon that an organic light emitting material emits light when excited by a current under the action of an electric field. Such electronic components generally include a cathode and an anode that are oppositely disposed, and a functional layer disposed between the cathode and the anode. The functional layer is composed of multiple 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, the organic electroluminescent device generally comprises 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 anode and the cathode, the two electrodes generate an electric field, electrons on the cathode side move to the electroluminescent layer under the action of the electric field, holes on 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 and 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 the carriers (electrons or holes) are injected so as to transport the 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. At present, the excellent performance of the triarylamine material in the hole transport layer material is one of the hot points of research. Although the prior art discloses materials that can be used to prepare hole transport layers in organic electroluminescent devices, the existing triarylamine-based hole transport layer materials do not perform well in terms of voltage, luminous efficiency, power, and lifetime in the devices. Therefore, there is still a need to develop new materials to further improve the performance of electronic components.
Disclosure of Invention
In view of the above problems in the prior art, it is an object of the present invention to provide an organic material, 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 the device, and improving the efficiency and lifetime of the device.
In order to achieve the above purpose, the following technical solutions are adopted in the present application:
according to a first aspect of the present application, there is provided an organic material having a structure represented by formula 1:
wherein X is selected from C (R) 1 R 2 ) Each R 1 And R 2 Each independently selected from hydrogen, deuterium or an alkyl group having 1 to 10 carbon atoms;
n is selected from 1,2 or 3, when n is more than or equal to 2, any two R 1 Identical or different, any two R 2 The same or different;
L、L 1 、L 2 and L 3 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar 1 and Ar 2 Each independently selected from substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted spirodibenzofluorenyl group;
Ar 3 selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms;
l, L 1 、L 2 、L 3 、Ar 1 And Ar 2 Wherein the substituents are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 5 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a halogenated aryl group having 6 to 20 carbon atoms, and a triarylsilyl group having 18 to 24 carbon atoms;
ar is 3 Wherein the substituents are the same or different and are independently selected from deuterium, halogen, cyano, alkyl having 1-10 carbon atoms, deuterated alkyl having 1-10 carbon atoms, cycloalkyl having 3-10 carbon atoms, aryl having 6-20 carbon atoms, deuterated aryl having 6-20 carbon atoms, halogenated aryl having 6-20 carbon atoms, and triarylsilyl having 18-24 carbon atoms;
optionally, in Ar 1 、Ar 2 And Ar 3 In (b), any two adjacent substituents form a ring.
According to a second aspect of the present application, there is provided an electronic component including an anode and a cathode which are oppositely disposed, and a functional layer provided between the anode and the cathode; the functional layer comprises the organic material described above.
According to a third aspect of the present application, there is provided an electronic device including the electronic component of the second aspect.
The core structure of the application is that triarylamine group and aryl group are combined by 1, 1-substitution of cycloalkyl group, and the aromatic group in the triarylamine group is selected from several specific groups. These specific groups allow a steric conjugation effect between the groups of the compound molecules. The molecule has proper HOMO energy level and higher hole mobility through the space conjugation effect, and is suitable for being used in a hole auxiliary layer of an organic electroluminescent device; meanwhile, the molecular structure has good amorphous stacking performance, so that the crystallinity of the material can be reduced, and the service life of a device can be prolonged; particularly, when the aromatic group in the triarylamine is selected to be a specific group, the electronic tolerance of the material can be effectively improved, so that the service life of the organic electroluminescent device is further prolonged.
Additional features and advantages of the present application will be described in detail in the detailed description which follows.
Drawings
The accompanying drawings, which are included to provide a further understanding of the application and are incorporated in and constitute a part of this specification, illustrate embodiments of the application and together with the description serve to explain the application and not to limit the application.
Fig. 1 is a schematic structural view of an organic electroluminescent device according to the present application.
Fig. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present disclosure.
Reference numerals
100. Anode 200, cathode 300, functional layer 310, hole injection layer
320. Hole transport layer 330, hole assist layer 340, organic light emitting layer 350, 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. The exemplary embodiments, however, may be embodied in many different 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 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 application.
In a first aspect, the present application provides an organic material having a structure represented by formula 1:
wherein X is selected from C (R) 1 R 2 ) Each R 1 And R 2 Each independently selected from hydrogen, deuterium or an alkyl group having 1 to 10 carbon atoms;
n is selected from 1,2 or 3, when n is more than or equal to 2, any two R 1 Identical or different, any two R 2 The same or different;
l is substituted or unsubstituted arylene with 6-30 carbon atoms, substituted or unsubstituted heteroarylene with 3-30 carbon atoms;
L 1 、L 2 and L 3 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar 1 and Ar 2 Each independently selected from substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted spirobifluorenyl group;
Ar 3 selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms;
l, L 1 、L 2 、L 3 、Ar 1 And Ar 2 Wherein the substituents are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 5 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a halogenated aryl group having 6 to 20 carbon atoms, and a triarylsilyl group having 18 to 24 carbon atoms;
ar is 3 Wherein the substituents are the same or different and are independently selected from deuterium, halogen, cyano, alkyl with 1-10 carbon atoms, deuterated alkyl with 1-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, aryl with 6-20 carbon atoms, deuterated aryl with 6-20 carbon atoms, halogenated aryl with 6-20 carbon atoms and triaryl silicon group with 18-24 carbon atoms;
optionally, at Ar 1 、Ar 2 And Ar 3 In (b), any two adjacent substituents form a ring.
According to a second aspect of the present application, there is provided an electronic component including an anode and a cathode which are oppositely disposed, and a functional layer provided between the anode and the cathode; the functional layer comprises the organic material described above.
In this application, the terms "optional" and "optionally" mean that the subsequently described event or circumstance may but need not occur, and that the description includes instances where the event or circumstance occurs or does not occur. For example, "optionally, two adjacent substituents form a ring; "means that these two substituents may but need not form a ring, including: a scenario where two adjacent substituents form a ring and a scenario where two adjacent substituents do not form a ring.
In the present application, "any two adjacent substituents form a ring," any two adjacent "may include two substituents on the same atom, and may also include one substituent on each of two adjacent atoms; wherein, when two substituents are present on the same atom, both substituents may form a saturated or unsaturated ring with the atom to which they are both attached; when two adjacent atoms have a substituent on each, the two substituents may be fused to form a ring. For example, when Ar 1 When there are 2 or more substituents and any adjacent substituent forms a ring, a saturated or unsaturated cyclic group is formed, for example: benzene ring, naphthalene ring, phenanthrene ring, anthracene ring, fluorene ring, cyclopentane, cyclohexane, adamantane, and the like.
In the present application, the fluorenyl group may be substituted with 1 or 2 substituents, wherein, in the case where the fluorenyl group is substituted, it may be:
and the like, but is not limited thereto.
In the application, the description mode of 'each 8230' \8230, independently 'and' 8230 '\8230' \ 8230 '\ independently' and 'each independently' and '8230' \\ 8230 '. The description modes are independently selected from' interchangeable and are to be broadly understood, and can mean that specific options expressed among the same symbols in different groups are not influenced with each other, and can also mean that specific options expressed among the same symbols in the same groups are not influenced with each other. For example,'
Wherein each q is independently 0, 1,2 or 3, each R "is independently selected from hydrogen, deuterium, fluoro, chloro" and has the meaning: the formula Q-1 represents a structure having Q substituents R 'on the benzene ring, and each R' may be the sameOr different, the options of each R' are not influenced mutually; the formula Q-2 represents that each benzene ring of biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on the 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 with each other.
As used herein, an delocalized linkage refers to a single bond extending from a ring system
It means that one end of the linkage may be attached to any position in the ring system through which the linkage extends, and the other end to the rest of the compound molecule.
For example, as shown in formula (f), naphthyl represented by formula (f) is connected to other positions of the molecule through two non-positioned bonds through the bicyclic ring, and the meaning of the naphthyl represented by the formula (f-1) includes any possible connection mode as shown in formula (f-10).
As another example, as shown in the following formula (X '), the dibenzofuranyl group represented by formula (X') is attached to another position of the molecule via an delocalized bond extending from the middle of the phenyl ring on one side, and the meaning thereof includes any of the possible attachment means as shown in the formulas (X '-1) -formula (X' -4).
In the present application, the term "substituted or unsubstituted" means that a functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Rc or an unsubstituted aryl group. The substituent Rc may be, for example, deuterium, a halogen group, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, a deuterated aryl group, a halogenated aryl group, or a triarylsilyl group.
In the present application, the number of carbon atoms of the substituted or unsubstituted functional group means all the number of carbon atoms. For example, if L 1 And is a substituted arylene group having 12 carbon atoms, all of the carbon atoms of the arylene group and the substituents thereon are 12 carbon atoms.
In this application, aryl refers to an optional functional group or substituent derived from an aromatic carbon ring. The aryl group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group can be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups joined by carbon-carbon bond conjugation, monocyclic aryl and fused ring aryl groups joined by carbon-carbon bond conjugation, two or more fused ring aryl groups joined by carbon-carbon bond conjugation. That is, unless otherwise specified, two or more aromatic groups conjugated through a carbon-carbon bond may also be considered as aryl groups herein. The fused ring aryl group may include, for example, a bicyclic fused aryl group (e.g., naphthyl group), a tricyclic fused aryl group (e.g., phenanthryl group, fluorenyl group, anthracyl group), and the like. The aryl group does not contain heteroatoms 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, anthracyl, phenanthryl, biphenyl, terphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl a benzofluoranthenyl group,
Spirobifluorenyl and the like. In this application, reference to arylene is to a divalent group formed by an aryl group further deprived of a hydrogen atom.
In this application, terphenyl comprises
In the present application, substituted aryl groups may be aryl groups in which one or two or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, alkyl groups, cycloalkyl groups, and the like. It is understood that the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituent on the aryl group, for example, a substituted aryl group having a carbon number of 18 refers to the total number of carbon atoms of the aryl group and the substituent being 18.
In the present application, heteroaryl refers to a monovalent aromatic ring 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, or derivatives thereof. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaryl group may be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds in a conjugated manner, and any one of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. Exemplary heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, and the like, without being limited thereto. Wherein, thienyl, furyl, phenanthroline group and the like are heteroaryl of a single aromatic ring system type, and N-phenyl carbazolyl and N-pyridyl carbazolyl are heteroaryl of a polycyclic system type connected by carbon-carbon bond conjugation. In this application, a heteroarylene group refers to a divalent group formed by a heteroaryl group further lacking one hydrogen atom.
In the present application, a substituted heteroaryl group may be a heteroaryl group in which one or two or more hydrogen atoms are substituted with a group such as deuterium atom, halogen group, cyano group, aryl group, heteroaryl group, alkyl group, cycloalkyl group, or the like. It is understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituent on the heteroaryl group.
In the present application, the number of carbon atoms of the substituted or unsubstituted aryl group may be 6 to 30, for example, the number of carbon atoms may be 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25 or 30.
Specific examples of the aryl group as the substituent in the present application include, but are not limited to, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, anthracyl,
And (4) a base.
In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl group may be 3 to 30, for example, the number of carbon atoms may be 3, 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 or 30.
Specific examples of heteroaryl groups as substituents in the present application include, but are not limited to, triazinyl, pyridyl, pyrimidyl, carbazolyl, dibenzofuranyl, dibenzothienyl, quinolyl, quinazolinyl, quinoxalinyl, isoquinolyl, carbazolyl, N-phenylcarbazolyl.
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, tert-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 number of carbon atoms of the cycloalkyl group having 3 to 10 carbon atoms may be, for example, 3,4, 5, 6, 7, 8 or 10. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl.
In the present application, specific examples of triarylsilyl groups having 18 to 24 carbon atoms include, but are not limited to, triphenylsilyl groups, and the like.
In the present application, specific examples of the deuterated alkyl group having 1 to 10 carbon atoms include, but are not limited to, a trideuteromethyl group.
Specific examples of deuterated aryl groups having a carbon number of from 6 to 20 in the present application include, but are not limited to, mono-deuterated phenyl, di-deuterated phenyl, tri-deuterated phenyl, tetra-deuterated phenyl, penta-deuterated phenyl.
Specific examples of the halogenated aryl group having 6 to 20 carbon atoms in the present application include, but are not limited to, monofluorophenyl group, difluorophenyl group, trifluorophenyl group, tetrafluorophenyl group and pentafluorophenyl group.
In some embodiments herein, the organic material is selected from compounds represented by formula 1-1 and formula 1-2:
in some embodiments of the present application, the R is 1 And R 2 Are all hydrogen.
In some embodiments herein, n is selected from 1 or 2.
In some embodiments of the present application, L is selected from substituted or unsubstituted arylene groups having 6 to 15 carbon atoms, substituted or unsubstituted heteroarylene groups having 12 to 20 carbon atoms.
Alternatively, the substituents in L are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, or a phenyl group.
In other embodiments herein, L is selected from the group consisting of substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted anthrylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranylene, and substituted or unsubstituted dibenzothiophenylene.
Alternatively, the substituents in said L are the same or different and are each independently selected from the group consisting of deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
In some embodiments of the present application, L is selected from a substituted or unsubstituted group W, wherein the unsubstituted group W is selected from the group consisting of:
the substituted group W has one or more substituents independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, or biphenyl, and when the number of the substituents is more than 1, each substituent is the same or different.
Alternatively, L is selected from the group consisting of:
in some embodiments of the present application, L 1 、L 2 And L 3 The same or different, each independently selected from a single bond or phenylene.
In other embodiments of the present application, L 1 、L 2 And L 3 The same or different, each independently selected from the group consisting of a single bond or the following groups:
in other embodiments of the present application, ar is 1 And Ar 2 Wherein the substituents are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms, a halogenated aryl group having 6 to 12 carbon atoms or a triphenylsilicon group;
optionally, at Ar 1 And Ar 2 Middle and renMeaning that two adjacent substituents form a saturated or unsaturated ring having 5 to 13 carbon atoms.
Alternatively, in Ar 1 And Ar 2 In (3), any two adjacent substituents may form cyclohexane
Cyclopentane (I)
Benzene ring
Naphthalene ring
Or a fluorene ring
Further optionally, the Ar 1 And Ar 2 The substituents in (A) are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, trideuteromethyl, pentadeutrophenyl, monofluorophenyl or triphenylsilyl.
In other embodiments of the present application, ar 1 And Ar 2 Identical or different, each independently selected from substituted or unsubstituted groups V, wherein the unsubstituted groups V are selected from the group of:
wherein, the substituted group V has one or more than two substituent groups, the substituent groups in the substituted group V are respectively and independently selected from the group consisting of deuterium, fluorine, cyano, phenyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, trideuteromethyl, pentadeuterophenyl, monofluorobenzyl or triphenylsilyl, and when the number of the substituent groups on the group V is more than 1, the substituent groups are the same or different.
Optionally, the Ar 1 And Ar 2 The same or different, each independently selected from the group consisting of:
in some embodiments of the present application, the,
each independently selected from the group consisting of:
alternatively,
each independently selected from the group consisting of:
in some embodiments of the present application, the,
selected from the group consisting of:
in some embodiments of the present application, ar is 3 Is a substituted or unsubstituted aryl group having 6 to 25 carbon atoms.
Optionally, the Ar 3 Wherein the substituents are the same and different, and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms or a phenyl group;
optionally, in Ar 3 In (b), any two adjacent substituents form a saturated or unsaturated ring having 5 to 13 carbon atoms.
Alternatively, in Ar 3 In (3), any two adjacent substituents may form cyclohexane
Cyclopentane
Benzene ring
Naphthalene ring
Or a fluorene ring
Optionally, the Ar is 3 Is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
Optionally, the Ar 3 Is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.
Further optionallyAr is said 3 Is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
In other embodiments of the present application, ar is 3 Selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted spirobifluorenyl.
Optionally, the Ar is 3 The substituents in (A) are the same and different, and are respectively and independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trideuteromethyl or phenyl.
In some embodiments of the present application, ar 3 Selected from substituted or unsubstituted groups G, wherein the unsubstituted group G is selected from the group consisting of:
the substituted group G has one or more substituents, the substituents in the substituted group G are each independently selected from the group consisting of deuterium, fluoro, cyano, phenyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trideuteromethyl, or phenyl, and when the number of substituents on the group G is greater than 1, each substituent is the same or different.
Optionally, the Ar 3 Selected from the group consisting of:
optionally, the organic material is selected from 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 to 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 element 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, a hole assist 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 disclosure, the organic electroluminescent device is a red organic electroluminescent device.
Optionally, the anode 100 comprises an anode material, which 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 metals and oxides, e.g. ZnO: al or SnO 2 Sb; or a conductive polymer such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but are not limited thereto. A transparent electrode including Indium Tin Oxide (ITO) as an anode is preferable.
Alternatively, the hole transport layer 320 includes one or more hole transport materials, and the hole transport material may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, which can be selected by those skilled in the art with reference to the prior art, and the present application is not limited thereto. In some embodiments of the present application, hole transport layer 330 is HT-15.
In one embodiment, the hole assist layer 330 is an organic material.
Optionally, a hole injection layer 310 may be further disposed 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 made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, which are not 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, the hole injection layer 310 is comprised of HAT-CN.
Alternatively, the organic light emitting layer 340 may be composed of a single light emitting layer material, or may 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 a hole injected into the organic light emitting layer 340 and an electron injected into the organic light emitting layer 340 may be recombined in the organic light emitting layer 340 to form an exciton, which transfers 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 is not particularly limited in the present application.
In some embodiments of the present application, the host material of the organic light emitting layer 340 is RH-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 is not particularly limited in the present application. The guest material is also referred to as a dopant material or dopant. Specific examples of the red phosphorescent dopant for the red organic electroluminescent device include but are not limited to,
in a more specific embodiment, the host material of the organic light emitting layer 340 is RH-01 of the present application and the guest material is Ir (piq) 2 (acac)。
The electron transport layer 350 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, which may be selected from, but not limited to, ET-01, liQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, and this application is not limited thereto. The material of the electron transport layer 350 includes, but is not limited to, the following compounds:
in some embodiments of the present application, electron transport layer 350 is comprised of ET-01 and LiQ.
In the present 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 multilayer 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.
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 the electronic component according to the second aspect of the present application.
According to one embodiment, as shown in fig. 2, the electronic device provided is an electronic device 400 comprising the above-described organic electroluminescent device. The electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, which may include, but are not limited to, a computer screen, a mobile phone screen, a television, electronic paper, an emergency light, an optical module, and the like.
The method for synthesizing the organic compound of the present application will be specifically described below with reference to the synthesis examples, but the present application is not limited thereto.
Compounds of synthetic methods not mentioned in this application are all commercially available starting products.
Synthetic examples
Synthesis of intermediate IM-a-1:
under the protection of nitrogen, 4-bromochlorobenzene (25.5g, 133.1mmol) and THF (150 mL) are added into a 500mL round-neck flask, the temperature of the system is reduced to-90 ℃ to-78 ℃, a tetrahydrofuran solution of n-butyl lithium (2 mol/L;79.9mL, 159.7mmol) is added dropwise to react for 1h at-90 ℃ to-78 ℃, then cyclopentanone (11.2g, 133.1mmol) is dissolved by THF (100 mL) and then is slowly added dropwise to the reaction system to react for 1h at-78 ℃ to-90 ℃, and then the reaction system is naturally raised to room temperature and stirred for 6h; adding dilute hydrochloric acid (260mL, 1mol/L) into the reaction system to terminate the reaction, adjusting the pH of the system to be weakly acidic, extracting with ethyl acetate and water, concentrating the organic layer under reduced pressure to obtain a crude product, recrystallizing the crude product with acetonitrile to obtain an intermediate IM-a-1 (17.0 g, yield 62%)
Referring to the synthesis method of the intermediate IM-a-1, cyclopentanone is replaced by raw material 1 and 4-bromochlorobenzene is replaced by raw material 2 in Table 1, and the intermediates shown in Table 1 are synthesized:
table 1: preparation of intermediates IM-a-2 to IM-a-14
Synthesis of intermediate IM-b-1
Intermediate IM-a-1 (19.7g, 100mmol), benzene (7.8g, 100mmol) and dichloromethane (200 mL) were added to a round bottom flask and trifluoromethanesulfonic acid (22.5g, 150mmol) was added dropwise at 0 ℃ and the reaction was stopped after 2 h; the reaction solution was extracted with dichloromethane and water, the organic phases were combined and washed twice with water, dried over anhydrous magnesium sulfate for half an hour, the organic phase was concentrated to dryness, and the crude product was recrystallized once from n-heptane to give intermediate IM-b-1 (19.2 g; yield 75%).
Referring to the synthesis method of the intermediate IM-b-1, the intermediate shown in Table 2 is synthesized by replacing the intermediate IM-a-1 with the raw material 3 and replacing the benzene with the raw material 4 in Table 2:
table 2: preparation of intermediates IM-b-2 to IM-b-25
Synthesis of Compound 1
Intermediate IM-b-1 (3.4 g, 13.1mmol), bis (4-biphenyl) amine (4.2g, 13.1mmol), tris (dibenzylideneacetone) dipalladium (0.2g, 0.3mmol), 2-dicyclohexylphosphonium-2, 6-dimethoxybiphenyl (0.2g, 0.5 mmol), sodium tert-butoxide (1.9g, 19.7 mmol) and toluene (50 mL) were added to a round bottom flask under nitrogen and allowed to react for 4 hours while stirring and warming to 105 ℃ to 110 ℃; cooling the reaction solution to room temperature, washing with water, separating an organic phase, drying with anhydrous magnesium sulfate, and removing the solvent under reduced pressure; the crude product was purified by column chromatography on silica gel using methylene chloride/n-heptane and then by recrystallization using toluene/n-heptane to give compound 1 as a white solid (4.8 g; yield 67%). Mass spectrum: m/z =542.3[ m ] +H ] +.
The compounds shown in Table 3 were synthesized by referring to the synthesis method of Compound 1 except that raw material 5 was used instead of intermediate IM-b-1 and raw material 6 was used instead of bis (4-biphenylyl) amine to prepare the compounds in Table 3 below
Table 3: compound structure preparation and characterization data
Some of the compounds and intermediate nuclear magnetic data are shown in table 4 below:
TABLE 4
Preparation and evaluation of organic electroluminescent device
Example 1: red organic electroluminescent device
The anode was prepared by the following procedure: mixing ITO with a solventA thickness of/Ag/ITO of
The glass substrate (manufactured by Corning) of (1) was cut into a size of 40mm x 0.7mm, prepared into an experimental substrate having a cathode, an anode and an insulating layer pattern using a photolithography process, using ultraviolet ozone and O 2 :N 2 The plasma was subjected to a surface treatment to increase the work function of the anode (experimental substrate) and remove scum.
Vacuum evaporation on the anode of the experimental substrate
HAT-CN (B) as a Hole Injection Layer (HIL), and then vapor-depositing the hole injection layer
And HT-15, forming a Hole Transport Layer (HTL).
Vacuum evaporating Compound 1 on the hole transport layer to form
Hole assist layer of
On the hole assist layer, RH-01 and Ir (piq) 2 (acac) co-evaporation to form
The organic light-emitting layer (R-EML).
And sequentially carrying out co-evaporation of ET-01 and LiQ on the light-emitting layer at a ratio of 1
The Electron Transport Layer (ETL) of (2), yb is deposited on the electron transport layer to form a layer having a thickness of
And then magnesium (Mg) and silver (Ag) are mixed in a ratio of 1: 9. is vacuum-evaporated on the electron injection layer to a thickness of
The cathode of (2).
Finally, the cathode is evaporated to a thickness of
HT-16, forming an organic capping layer (CPL), thereby completing the fabrication of the organic light emitting device.
Examples 2 to 35
An organic electroluminescent device was fabricated by the same method as example 1, except that compounds shown in table 6 below were substituted for compound 1 in forming the hole assist layer.
Comparative examples 1 to 6
An organic electroluminescent device was fabricated in the same manner as in example 1, except that compound a, compound B, compound C, compound D, compound E, and compound F in table 6 below were each substituted for compound 1 in forming the hole-assist layer.
Among them, the other material structures used in the above examples and comparative examples are shown in the following Table 5
TABLE 5
The devices of examples 1-35 and comparative examples 1-6 were operated at 10mA/cm 2 IVL (Current, voltage, luminance, etc.) was tested at a current density of 20mA/cm 2 The current density was measured for T95 lifetime, the results of which are shown in Table 6 below.
TABLE 6 device Performance test results
From the results of table 6 above, it is understood that the organic electroluminescent devices of examples 1 to 35 are improved in performance as compared with the organic electroluminescent devices of comparative examples 1 to 6. Specifically, the driving voltages of the organic electroluminescent devices of examples 1 to 35 were close to those of the comparative examples, and the current efficiency was improved by at least 15.5% and the lifetime was improved by at least 10.2%. Therefore, the organic material is used as a hole auxiliary layer of an organic electroluminescent device, and the efficiency are improved while the low working voltage is kept.
In examples 1 to 35 of the present application, the current efficiency was improved by at least 26% and the lifetime was improved by at least 10.2% as compared with comparative example a and comparative example F. The reason for this may be that, in the triarylamine group in the compound a and the compound F, a specific binaphthyl group is selected as an aryl moiety, and the binaphthyl group is linked to an amine group, so that the T1 level of the compound is lowered, thereby lowering the efficiency of the organic electroluminescent device.
In examples 1 to 35 of the present application, compared to comparative examples B, C, and D, the current efficiency was improved by at least 15.5%, and the lifetime was improved by at least 20.4%. The reason for this is probably that the aryl group in the triarylamine group of the compound B, the compound C and the compound D is selected from phenyl or benzyl, and the conjugation range of the phenyl or benzyl is small, so that the molecular stability of the compound is insufficient, and the lifetime of the effective electroluminescent device is reduced.
The core structure of the application is that triarylamine group and aryl group are combined by 1, 1-substitution of cycloalkyl group, and the aromatic group in the triarylamine group is selected from several specific groups. These specific groups allow a steric conjugation effect between the groups of the compound molecules. The molecule has proper HOMO energy level and higher hole mobility through the space conjugation effect, and is suitable for being used in a hole auxiliary layer of an organic electroluminescent device; meanwhile, the molecular structure has good amorphous stacking performance, so that the crystallinity of the material can be reduced, and the service life of a device can be prolonged; particularly, when the aromatic group in the triarylamine is selected to be a specific group, the electronic tolerance of the material can be effectively improved, and the service life of the organic electroluminescent device can be further prolonged. Especially when the cycloalkyl group is cyclopentane, the device performance is better.
It will be understood that the present application is not limited to the precise arrangements described above and shown in the drawings and that various modifications and changes may be made without departing from the scope thereof. The scope of the application is limited only by the appended claims.
Claims (14)
1. An organic material having a structure represented by formula 1:
wherein X is selected from C (R) 1 R 2 ) Each R 1 And R 2 Each independently selected from hydrogen, deuterium or an alkyl group having 1 to 10 carbon atoms;
n is selected from 1,2 or 3, when n is more than or equal to 2, any two R 1 Identical or different, any two R 2 The same or different;
l is substituted or unsubstituted arylene with 6-30 carbon atoms, substituted or unsubstituted heteroarylene with 3-30 carbon atoms;
L 1 、L 2 and L 3 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar 1 and Ar 2 Each independently selected from substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted spirobifluorenyl group;
Ar 3 selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms;
l, L 1 、L 2 、L 3 、Ar 1 And Ar 2 Wherein the substituents are the same or different and are independently selected from deuterium and halogenA group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 5 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a halogenated aryl group having 6 to 20 carbon atoms, and a triarylsilyl group having 18 to 24 carbon atoms;
ar is 3 Wherein the substituents are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a halogenated aryl group having 6 to 20 carbon atoms, and a triarylsilyl group having 18 to 24 carbon atoms;
optionally, in Ar 1 、Ar 2 And Ar 3 In (b), any two adjacent substituents form a ring.
2. The organic material according to claim 1, wherein the organic material is selected from compounds represented by formula 1-1 and formula 1-2:
3. the organic material of claim 1, wherein L is selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, a substituted or unsubstituted heteroarylene group having 12 to 20 carbon atoms;
preferably, the substituents in L are the same or different and are respectively and independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms or a phenyl group.
4. The organic material of claim 1, wherein L is selected from the group consisting of substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted anthrylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene;
preferably, the substituents in said L are the same or different and are each independently selected from the group consisting of the same or different and are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
5. The organic material of claim 1, wherein L is 1 、L 2 And L 3 The same or different, each independently selected from a single bond or phenylene.
6. The organic material of claim 1, wherein Ar is Ar 1 And Ar 2 Wherein the substituents are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms, a halogenated aryl group having 6 to 12 carbon atoms or a triphenylsilicon group;
optionally, in Ar 1 And Ar 2 In (b), any two adjacent substituents form a saturated or unsaturated ring having 5 to 13 carbon atoms.
7. The organic material according to claim 1,
each independently selected from the group consisting of:
8. the organic material of claim 1, wherein Ar is Ar 3 Is substituted or unsubstituted aryl with 6 to 25 carbon atoms;
preferably, it isAr is said 3 Wherein the substituents are the same and different, and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms or a phenyl group;
optionally, at Ar 3 In (b), any two adjacent substituents form a saturated or unsaturated ring having 5 to 13 carbon atoms.
9. The organic material of claim 1, wherein Ar is Ar 3 Selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted spirobifluorenyl;
preferably, ar is 3 The substituents in (A) are the same and different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trideuteromethyl or phenyl.
10. The organic material of claim 1, wherein Ar is Ar 3 Selected from the group consisting of:
11. the organic material of claim 1, wherein the organic material is selected from the group consisting of:
12. an electronic component comprising an anode and a cathode disposed opposite one another, and a functional layer disposed between the anode and the cathode; characterized in that the functional layer comprises an organic material according to any one of claims 1 to 11.
13. The electronic component of claim 12, wherein the functional layer comprises a hole assist layer comprising the organic material;
optionally, the electronic element is an organic electroluminescent device.
14. An electronic device, characterized by comprising the electronic component of claim 12 or 13.
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| CN202210407500.1A CN115521212B (en) | 2022-04-19 | 2022-04-19 | Organic material, electronic element and electronic device |
| PCT/CN2023/076636 WO2023202198A1 (en) | 2022-04-19 | 2023-02-16 | Organic material, electronic element, and electronic apparatus |
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| WO2023202198A1 (en) * | 2022-04-19 | 2023-10-26 | 陕西莱特光电材料股份有限公司 | Organic material, electronic element, and electronic apparatus |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5077142A (en) * | 1989-04-20 | 1991-12-31 | Ricoh Company, Ltd. | Electroluminescent devices |
| CN109456256A (en) * | 2018-12-28 | 2019-03-12 | 武汉天马微电子有限公司 | Compound, display panel and display device |
| CN113636945A (en) * | 2020-05-11 | 2021-11-12 | 北京鼎材科技有限公司 | Compound and application thereof |
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| CN110283084B (en) * | 2019-07-02 | 2023-05-26 | 武汉华星光电半导体显示技术有限公司 | Electroluminescent material, preparation method of electroluminescent material and light-emitting device |
| US20230200219A1 (en) * | 2020-05-11 | 2023-06-22 | Beijing Eternal Material Technology Co., Ltd | A compound, an organic electroluminescent device and a display device |
| CN115521212B (en) * | 2022-04-19 | 2024-03-22 | 陕西莱特光电材料股份有限公司 | Organic material, electronic element and electronic device |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5077142A (en) * | 1989-04-20 | 1991-12-31 | Ricoh Company, Ltd. | Electroluminescent devices |
| CN109456256A (en) * | 2018-12-28 | 2019-03-12 | 武汉天马微电子有限公司 | Compound, display panel and display device |
| CN113636945A (en) * | 2020-05-11 | 2021-11-12 | 北京鼎材科技有限公司 | Compound and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2023202198A1 (en) * | 2022-04-19 | 2023-10-26 | 陕西莱特光电材料股份有限公司 | Organic material, electronic element, and electronic apparatus |
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| CN115521212B (en) | 2024-03-22 |
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