CN117534575A - Organic compound, and electronic component and electronic device using same - Google Patents
Organic compound, and electronic component and electronic device using same Download PDFInfo
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- CN117534575A CN117534575A CN202311333353.9A CN202311333353A CN117534575A CN 117534575 A CN117534575 A CN 117534575A CN 202311333353 A CN202311333353 A CN 202311333353A CN 117534575 A CN117534575 A CN 117534575A
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 104
- 239000010410 layer Substances 0.000 claims description 87
- 125000003118 aryl group Chemical group 0.000 claims description 55
- -1 cyano, trimethylsilyl Chemical group 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 20
- 229910052805 deuterium Inorganic materials 0.000 claims description 19
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 18
- 239000002346 layers by function Substances 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000001188 haloalkyl group Chemical group 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 235000010290 biphenyl Nutrition 0.000 claims description 10
- 239000004305 biphenyl Substances 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 125000005549 heteroarylene group Chemical group 0.000 claims description 7
- 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 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 6
- 125000005561 phenanthryl group Chemical group 0.000 claims description 5
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- 125000005345 deuteroalkyl group Chemical group 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical class C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 claims description 2
- BKCGUEOCKLKNKK-UHFFFAOYSA-N C12(CCCCC1)C=CC=C1C3=CC=CC=C3C=C12 Chemical class C12(CCCCC1)C=CC=C1C3=CC=CC=C3C=C12 BKCGUEOCKLKNKK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 230000005525 hole transport Effects 0.000 description 35
- 239000000463 material Substances 0.000 description 30
- 150000001875 compounds Chemical class 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 15
- 238000002347 injection Methods 0.000 description 14
- 239000007924 injection Substances 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 239000010408 film Substances 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 238000005406 washing Methods 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
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 125000003107 substituted aryl group Chemical group 0.000 description 4
- 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 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
- 150000004982 aromatic amines Chemical class 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
- 238000004519 manufacturing process Methods 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-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
- 239000002585 base Substances 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical group C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 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
- 239000000543 intermediate Substances 0.000 description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 230000008569 process Effects 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
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- 150000005045 1,10-phenanthrolines Chemical class 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XESMNQMWRSEIET-UHFFFAOYSA-N 2,9-dinaphthalen-2-yl-4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC(C=2C=C3C=CC=CC3=CC=2)=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=C(C=3C=C4C=CC=CC4=CC=3)N=C21 XESMNQMWRSEIET-UHFFFAOYSA-N 0.000 description 1
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 description 1
- QRXMUCSWCMTJGU-UHFFFAOYSA-N 5-bromo-4-chloro-3-indolyl phosphate Chemical compound C1=C(Br)C(Cl)=C2C(OP(O)(=O)O)=CNC2=C1 QRXMUCSWCMTJGU-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001454 anthracenes Chemical class 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
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 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
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=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
- 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
- 239000010406 cathode material Substances 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000003153 chemical reaction reagent 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
- 239000011365 complex material Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229940125904 compound 1 Drugs 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
- 125000004122 cyclic group Chemical group 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
- 150000001975 deuterium Chemical group 0.000 description 1
- 125000004431 deuterium atom Chemical group 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Chemical group C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- ARHBTEUOFBNCQI-UHFFFAOYSA-N ethane-1,2-diol;methanol Chemical compound OC.OC.OCCO ARHBTEUOFBNCQI-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 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
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [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
- 239000003960 organic solvent Substances 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
- 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
- 125000003367 polycyclic group Chemical group 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
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000010248 power generation Methods 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical class [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 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
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005649 substituted arylene group Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
- C07C211/57—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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- C07D209/00—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
- C07D209/88—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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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- 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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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
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- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- C07C2603/10—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
- 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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- Electroluminescent Light Sources (AREA)
Abstract
The present invention relates to an organic compound, and an electronic component and an electronic device using the same. The organic compound has a structure shown in a formula I, and can be applied to an organic electroluminescent device to remarkably improve the performance of the device.
Description
Technical Field
The present invention relates to the field of organic electroluminescence, and in particular, to an organic compound, and an electronic element and an electronic device using the same.
Background
Along with the development of electronic technology and the progress of material science, the application range of electronic components for realizing electroluminescence or photoelectric conversion is becoming wider and wider. Such electronic components typically include oppositely disposed cathodes and anodes, and a functional layer disposed between the cathodes and anodes. The functional layer is composed of a plurality of organic or inorganic film layers and generally includes an energy conversion layer, a hole transport layer between the energy conversion layer and the anode, and an electron transport layer between the energy conversion layer and the cathode.
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.
Disclosure of Invention
An object of the present application is to provide an organic compound, and an electronic component and an electronic device using the same, which can improve the performance of an organic electroluminescent device.
A first aspect of the present application provides an organic compound having a structure represented by formula I:
wherein R is 1 And R is 2 And are the same or different and are each independently selected from an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms or an aryl group having 6 to 18 carbon atoms, or R 1 And R is 2 The carbon atoms to which they are attached together form a saturated or unsaturated 3-to 15-membered ring;
each R is independently selected from deuterium, halogen group, cyano, trialkylsilyl with 3-10 carbon atoms, alkyl with 1-10 carbon atoms, halogenated alkyl with 1-10 carbon atoms, deuterated alkyl with 1-10 carbon atoms, aryl with 6-20 carbon atoms or heteroaryl with 3-20 carbon atoms;
n represents the number of R, n is selected from 0, 1,2, 3,4, 5 or 6;
L 1 and L 2 The same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar 1 and Ar is a group 2 The same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
L 1 、L 2 、Ar 1 and Ar is a group 2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano group, trialkylsilyl group having 3 to 10 carbon atoms, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuteroalkyl group having 1 to 10 carbon atoms, aryl group having 6 to 20 carbon atoms or heteroaryl group having 3 to 20 carbon atoms.
A second aspect of 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 the organic compound.
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.
The parent nucleus of the compound is fluorenyl, and 3-phenyl substituted by 1, 2-phenyl is connected on the same benzene ring of the fluorenylAnd aromatic amines; on one hand, the special connection mode can greatly enhance the space configuration capacity of molecules by two substituent groups on the same benzene ring of fluorenyl, promote the glass transition temperature of the material and improve the film forming property of the material; on the other hand, the aromatic amine and the phenyl substituted by the 1, 2-position phenyl are connected on the same benzene ring of the fluorenyl, and the connection mode enlarges the conjugated area of the molecule, so that the compound has proper HOMO and LUMO energy levels and higher hole mobility. The compound can be used as a hole transport material, so that the carrier balance in the luminescent layer can be improved, the carrier composite region can be widened, and the device efficiency and the service life can be improvedAnd (5) a life.
Additional features and advantages of the present application will be set forth in the detailed description which follows.
Drawings
The accompanying drawings are included to provide a further understanding of the application and are incorporated in and constitute a part of this specification, illustrate the application and, together with the description, do not limit the application.
Fig. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of the present application.
Fig. 2 is a schematic diagram of a first electronic device according to an embodiment of the present application.
Fig. 3 is a schematic structural view of a photoelectric conversion device according to an embodiment of the present application.
Fig. 4 is a schematic diagram of a second electronic device according to an embodiment of the present application.
Description of the reference numerals
100. An anode; 200. a cathode; 300. a functional layer; 310. a hole injection layer; 320. a hole transport layer; 321. a first hole transport layer; 322. a second hole transport layer; 330. an organic light emitting layer; 340. an electron transport layer; 350. an electron injection layer; 360. a photoelectric conversion layer; 400. a first electronic device; 500. and a second 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 I:
wherein R is 1 And R is 2 And are the same or different and are each independently selected from an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms or an aryl group having 6 to 18 carbon atoms, or R 1 And R is 2 The carbon atoms to which they are attached together form a saturated or unsaturated 3-to 15-membered ring;
each R is independently selected from deuterium, halogen group, cyano, trialkylsilyl with 3-10 carbon atoms, alkyl with 1-10 carbon atoms, halogenated alkyl with 1-10 carbon atoms, deuterated alkyl with 1-10 carbon atoms, aryl with 6-20 carbon atoms or heteroaryl with 3-20 carbon atoms;
n represents the number of R, n is selected from 0, 1,2, 3,4, 5 or 6;
L 1 and L 2 The same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar 1 and Ar is a group 2 The same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
L 1 、L 2 、Ar 1 and Ar is a group 2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano group, trialkylsilyl group having 3 to 10 carbon atoms, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuteroalkyl group having 1 to 10 carbon atoms, aryl group having 6 to 20 carbon atoms or heteroaryl group having 3 to 20 carbon atoms.
In the present application, the description that "each independently selected from" and "each independently selected from" are used interchangeably is to be understood in a broad sense, which may mean that the specific options expressed between the same symbols in different groups do not affect each other,it may also be expressed that specific options expressed between the same symbols in the same group do not affect each other. For example, the number of the cells to be processed,wherein each q is independently 0, 1,2 or 3, and each R "is independently selected from hydrogen, deuterium, fluorine, chlorine", with the meaning: the formula Q-1 represents Q substituent groups R ' on the benzene ring, wherein R ' can be the same or different, and the options of each R ' are not mutually influenced; the formula Q-2 represents that each benzene ring of the biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on two benzene rings can be the same or different, each R 'can be the same or different, and the options of each R' are not influenced each other.
In the present application, such terms as "substituted or unsubstituted" mean that the functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl or unsubstituted aryl having a substituent Rc. Wherein the substituent Rc may be, for example, deuterium, a halogen group, cyano, alkyl, trialkylsilyl, haloalkyl, cycloalkyl, aryl, heteroaryl, etc.
In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to all the numbers of carbon atoms. For example, if L 1 Is a substituted arylene group having 12 carbon atoms, then the arylene group and all of the substituents thereon have 12 carbon atoms.
Aryl in this application refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group may be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups connected by carbon-carbon bonds, a monocyclic aryl group and a condensed ring aryl group connected by carbon-carbon bonds, two or more condensed ring aryl groups connected by carbon-carbon bonds. That is, unless otherwise indicated, two or more aromatic groups linked by carbon-carbon bonds may also be considered aryl groups herein. Wherein the fused ring aryl groups may include, for example, bicyclic fused aryl groups (e.g., naphthyl), tricyclic fused aryl groupsRadicals (e.g., phenanthryl, fluorenyl, anthracyl), and the like. The aryl group does not contain hetero atoms such as B, N, O, S, P, se, si and the like. For example, in the present application, biphenyl, terphenyl, and the like are aryl groups. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl,A base, etc. 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, a substituted aryl group may be one in which one 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, a trialkylsilyl group, an alkyl group, a cycloalkyl group, a haloalkyl group, a deuterated alkyl group, or the like. Specific examples of heteroaryl substituted aryl groups include, but are not limited to, dibenzofuranyl substituted phenyl, dibenzothiophene substituted phenyl, pyridine substituted phenyl, and 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 at least one heteroatom in the ring, which may be one or more 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 linked by carbon-carbon bonds, with either aromatic ring system being an aromatic monocyclic ring or an aromatic fused ring. Illustratively, heteroaryl groups may include 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, thiophenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, and the like, without limitation thereto. 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 groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, haloalkyl groups, deuterated alkyl groups, and the like. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothienyl, phenyl-substituted pyridyl, and 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 number of carbon atoms of the aryl group as a substituent may be 6 to 20, for example, the number of carbon atoms may be 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, and specific examples of the aryl group as a substituent include, but are not limited to, phenyl, biphenyl, naphthyl, anthracenyl,A base.
In the present application, the heteroaryl group as a substituent may have 3 to 20 carbon atoms, for example, 3,4, 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms, and specific examples of the heteroaryl group as a substituent include, but are not limited to, pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothienyl, quinolinyl, quinazolinyl, quinoxalinyl, isoquinolinyl.
In the present application, the carbon number of the alkyl group having 1 to 10 carbon atoms 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-heptyl, 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.
Specific examples of trialkylsilyl groups herein include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.
Specific examples of haloalkyl groups herein include, but are not limited to, trifluoromethyl.
Specific examples of deuterated alkyl groups herein include, but are not limited to, tridentate methyl.
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, cyclopentane, cyclohexane, adamantane.
In the present application, non-positional connection means a single bond extending from a ring systemIt means that one end of the bond can be attached to any position in the ring system through which the bond extends, and the other end is attached to the remainder of the compound molecule. For example, as shown in formula (f), the naphthyl group represented by formula (f) is linked 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) to (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 the formula (X ' -1) to (X ' -4) includes any possible linkage as shown in the formula (X ' -1):
in some embodiments of the present application, R 1 And R is 2 Identical or different and are each independently selected from methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, tridentate methyl, phenyl, naphthyl or biphenyl, or R 1 And R is 2 To which are co-linked carbon atoms to form cyclopentaneCyclohexane->Or fluorene ring->
In some embodiments of the present application, the organic compound has a structure represented by formula 1, formula 2, formula 3, formula 4, formula 5, formula 6, formula 7, formula 8, formula 9, formula 10, formula 11, or formula 12 below:
in some embodiments of the present application, each R is independently selected from deuterium, fluoro, cyano, trimethylsilyl, methyl, ethyl, isopropyl, t-butyl, trifluoromethyl, tridentate methyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl, or carbazolyl.
In some embodiments of the present application, L 1 And L 2 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms. For example, L 1 And L 2 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atomsOr a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.
Alternatively, L 1 And L 2 The substituents in (a) are each independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, alkyl having 1 to 5 carbon atoms, or phenyl.
In some embodiments of the present application, L 1 And L 2 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.
Alternatively, L 1 And L 2 Each of the substituents is independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, methyl, ethyl, isopropyl, t-butyl, or phenyl.
In some embodiments of the present application, L 1 And L 2 Each independently selected from the group consisting of a single bond or:
alternatively, L 1 And L 2 Each independently selected from the group consisting of a single bond or:
in some embodiments of the present application, ar 1 And Ar is a group 2 Each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms and a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms. For example, ar 1 And Ar is a group 2 Each independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 10, 20, 21, 22, 23, 24, or 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17, or 18 carbon atoms.
Alternatively, ar 1 And Ar is a group 2 The substituents in (a) are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, alkyl having 1 to 5 carbon atoms, haloalkyl having 1 to 5 carbon atoms, deuterated alkyl having 1 to 5 carbon atoms, aryl having 6 to 12 carbon atoms, and heteroaryl having 5 to 12 carbon atoms.
In some embodiments of the present application, ar 1 And Ar is a group 2 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorene, substituted or unsubstituted cyclopentane spirofluorene, substituted or unsubstituted cyclohexane spirofluorene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, and substituted or unsubstituted carbazolyl.
Alternatively, ar 1 And Ar is a group 2 Each of the substituents in (a) is independently selected from deuterium, fluoro, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, t-butyl, tridentate methyl or phenyl.
In some embodiments of the present application, ar 1 And Ar is a group 2 Each independently selected from the group consisting of:
further alternatively, ar 1 And Ar is a group 2 Each independently selected from the group consisting of:
in some embodiments of the present application,identical or different and are each independently selected from the group consisting of:
alternatively, the process may be carried out in a single-stage,identical or different and are each independently selected from the group consisting of:
specifically, the organic compound is selected from the group consisting of:
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 functional layer includes a hole transport layer, the hole transport layer including the organic compound.
Optionally, the electronic element is an organic electroluminescent device or a photoelectric conversion device.
Optionally, the organic electroluminescent device is a red organic electroluminescent device.
Further optionally, the hole transport layer comprises a first hole transport layer and a second hole transport layer, the first hole transport layer being closer to the anode than the second hole transport layer, wherein the second hole transport layer comprises an organic compound of the present application.
In one embodiment, the electronic component is an organic electroluminescent device. As shown in fig. 1, the organic electroluminescent device may include an anode 100, a first hole transport layer 321, a second hole transport layer 322, an organic light emitting layer 330, an electron transport layer 340, and a cathode 200, which are stacked. Wherein the first hole transport layer 321 and the second hole transport layer 322 constitute the hole transport layer 320.
Alternatively, the anode 100 includes an anode material that is preferably 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. Preferably, a transparent electrode including Indium Tin Oxide (ITO) as an anode is included.
Optionally, the hole transport layer includes one or more hole transport materials, which may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, which are not specifically defined herein. For example, the material of the first hole transport layer is selected from the group consisting of:
in one embodiment, the first hole transport layer 321 is HT-1.
In another embodiment, second hole transport layer 322 is a compound of the present application.
Alternatively, the organic light emitting layer 330 may be composed of a single light emitting layer material, and may include a host material and a guest material. Alternatively, the organic light emitting layer 330 is composed of a host material and a guest material, and holes injected into the organic light emitting layer 330 and electrons injected into the organic light emitting layer 330 may be recombined at the organic light emitting layer 330 to form excitons, which transfer energy to the host material, which transfers energy to the guest material, thereby enabling the guest material to emit light.
The host material of the organic light emitting layer 330 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. The host material may be a single host material or a mixed host material. In one embodiment of the present application, the host material of the organic light emitting layer 330 is CBP.
The guest material of the organic light emitting layer 330 may be selected with reference to the related art, and may be selected from iridium (III) organometallic complexes, platinum (II) organometallic complexes, ruthenium (II) complexes, and the like, for example. Specific examples of guest materials include but are not limited to,
in one embodiment of the present application, the guest material of the organic light emitting layer 330 is Ir (piq) 2 (acac)。
Alternatively, the electron transport layer 340 may be a single layer structure or a multi-layer structure, and may include one or more electron transport materials, which may generally include a metal complex or/and a nitrogen-containing heterocyclic derivative, wherein the metal complex material may be selected from, for example, liQ, alq 3 Etc.; the nitrogen-containing heterocyclic derivative may be an aromatic ring having a nitrogen-containing six-membered ring or five-membered ring skeleton, a condensed aromatic ring having a nitrogen-containing six-membered ring or five-membered ring skeleton, or the like, and specific examples include, but are not limited to, 1, 10-phenanthroline compounds such as Bphen, NBphen, ET-21, bimiBphen, or the like, or heteroaryl-containing anthracene compounds, triazine compounds, or pyrimidine compounds having the structures shown below. In one embodiment of the present application, electron transport layer 340 is comprised of ET-20 and LiQ.
In this application, cathode 200 may include a cathodeA material that is a material with a small work function that helps electron injection material 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. A metal electrode containing magnesium and silver is preferably included as a cathode.
Optionally, as shown in fig. 1, a hole injection layer 310 is further disposed between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321. 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. For example, the hole injection layer 310 contains a compound selected from the group consisting of:
in one embodiment of the present application, hole injection layer 310 is m-MTDATA.
Optionally, as shown in fig. 1, an electron injection layer 350 is further provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 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. For example, the electron injection layer 350 includes LiQ.
According to another embodiment, the electronic component is a photoelectric conversion device. As shown in fig. 3, the photoelectric conversion device may include an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 comprises an organic compound provided herein.
According to a specific embodiment, as shown in fig. 3, the photoelectric conversion device includes an anode 100, a hole transport layer 320, a photoelectric conversion layer 360, an electron transport layer 340, and a cathode 200, which are sequentially stacked. Optionally, the hole transport layer 320 comprises an organic compound of the present application.
Alternatively, the photoelectric conversion device may be a solar cell, in particular, an organic thin film solar cell. For example, in one embodiment of the present application, a solar cell includes an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode, which are sequentially stacked, wherein the hole transport layer includes an organic compound of the present application.
In a third aspect, the present application provides an electronic device comprising the electronic component provided in the second aspect of the present application.
According to one embodiment, as shown in fig. 2, the electronic device is a first electronic device 400, and the first electronic device 400 includes the organic electroluminescent device described above. The first electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, and may include, for example, but not limited to, a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting device, an optical module, etc.
According to another embodiment, as shown in fig. 4, the electronic device is a second electronic device 500, and the second electronic device 500 includes the above-mentioned photoelectric conversion device. The second electronic device 500 may be, for example, a solar power generation device, a light detector, a fingerprint identification device, a light module, a CCD camera, or other type of electronic device.
The synthesis method of the organic compound of the present application is specifically described below in connection with synthesis 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.
Synthesis example
1. Synthesis of IM a-I:
introducing nitrogen (0.100L/min) into a three-necked flask equipped with mechanical stirring, thermometer and spherical condenser for replacement3-chloro-2-bromo-1-iodobenzene (100.0 g,315.1 mmol), phenylboronic acid (80.68 g,661.7 mmol), bis (triphenyl) palladium dichloride (Pd (PPh) 3 ) 2 Cl 2 2.21g,3.15 mmol) and potassium carbonate (K 2 CO 3 130.65g,945.33 mmol) and a mixed solvent of dimethanol ethylenediether (DME, 800 mL) in water (200 mL) was added. Stirring is started, the temperature is raised to 75-78 ℃ for reaction for 56h, and after the reaction is finished, the reaction is cooled to room temperature. Washing the reaction solution with water, separating an organic phase, drying the organic phase by using anhydrous magnesium sulfate, filtering, and distilling the filtrate under reduced pressure to remove a solvent; purification of the crude product by silica gel column chromatography using a dichloromethane/n-heptane system afforded IM a-1 (66.74 g, 80% yield) as a white solid.
2. Synthesis of IM a-II:
a three-necked flask equipped with a mechanical stirrer, a thermometer and a spherical condenser was purged with nitrogen (0.100L/min) for 15 minutes, and IM a-I (66.7 g,251.9 mmol), pinacol biborate (70.22 g,277.1 mmol), tris (dibenzylideneacetone) dipalladium (Pd) were sequentially added 2 (dba) 3 2.31g,2.5 mmol), 2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl (X-Phos, 2.40g,5.0 mmol), potassium acetate (49.43 g,503.87 mmol) and 1, 4-dioxane (660 mL). Stirring is started, the temperature is raised to 92-100 ℃ for reaction for 6 hours, and after the reaction is finished, the mixture is cooled to room temperature. Washing the reaction solution with water, separating an organic phase, drying the organic phase by using anhydrous magnesium sulfate, filtering, and distilling the filtrate under reduced pressure to remove a solvent; purification of the crude product by silica gel column chromatography using a dichloromethane/n-heptane system afforded IM a-II (73.60 g, 82% yield) as a white solid.
3. Synthesis of IM a-III:
introducing nitrogen (0.100L/min) into a three-necked flask equipped with mechanical stirring, thermometer and spherical condenser tubeAfter 15min, IM a-II (73.60 g,206.58 mmol), reactant A (63.55 g,206.58 mmol), bis (triphenyl) palladium dichloride (Pd (Ph) 3 P) 2 Cl 2 0.725g,2.06 mmol) and potassium carbonate (71.38 g,516.46 mmol) and a mixed solvent of dimethanol ethyleneglycol (736 mL) and water (147.2 mL) was added. Stirring is started, the temperature is raised to 75-78 ℃ for reaction for 12 hours, and after the reaction is finished, the mixture is cooled to room temperature. Washing the reaction solution with water, separating an organic phase, drying the organic phase by using anhydrous magnesium sulfate, filtering, and distilling the filtrate under reduced pressure to remove a solvent; purification of the crude product by silica gel column chromatography using a dichloromethane/n-heptane system afforded IM a-III as a white solid (66.09 g, yield 72%).
The procedure referred to IM a-III was used to synthesize the intermediates listed in Table 1, using the main reagents, synthesized intermediates IM a-II, unchanged except that starting material listed in Table 1 was used in place of reactant A, with the yields shown in Table 1.
TABLE 1
Synthesis example 1: synthesis of Compound 2
To a three-necked flask equipped with a mechanical stirrer, a thermometer and a spherical condenser tube were introduced nitrogen (0.200L/min) for 15min for replacement, IMj-III (15 g,32.82 mmol), 4-aminobiphenyl (5.55 g,32.82 mmol), tris (dibenzylideneacetone) dipalladium (0.15 g,0.16 mmol), 2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl (0.16 g,0.33 mmol), sodium t-butoxide (t-Buona, 4.73g,49.23 mmol) and toluene (PhMe, 150 mL) were sequentially added, followed by reflux reaction at 105℃to 110℃for 3h, and after the completion of the reaction, cooling to room temperature was performed. Washing the organic phase with water, adding anhydrous magnesium sulfate, drying the organic phase, filtering, and distilling the filtrate under reduced pressure to remove the solvent; purification of the crude product by silica gel column chromatography using a dichloromethane/n-heptane system afforded IM 2-1 (15.48 g, 76% yield) as a white solid.
A three-necked flask equipped with a mechanical stirrer, a thermometer and a spherical condenser was purged with nitrogen (0.100L/min) for 15 minutes, IM 2-1 (15 g,25.43 mmol), 4-bromobiphenyl (5.93 g,25.43 mmol), tris (dibenzylideneacetone) dipalladium (0.116 g,0.13 mmol), 2-dicyclohexylphosphine-2, 6-dimethoxybiphenyl (S-Phos, 0.11g,0.25 mmol), sodium t-butoxide (3.67 g,38.15 mmol) and toluene (150 mL) were sequentially added, followed by reflux reaction at 105℃to 110℃for 6 hours, and after the completion of the reaction, the reaction was cooled to room temperature. Washing the organic phase with water, separating liquid, adding anhydrous magnesium sulfate to dry the organic phase, filtering, and distilling the filtrate under reduced pressure to remove the solvent; purification of the crude product by silica gel column chromatography using methylene chloride/n-heptane system gave compound 1 (8.49 g, yield 47%) as a white solid. Mass spectrum (m/z) =742.3 [ m+h] + 。
The procedure for reference to compound 2 was used to synthesize the compounds listed in table 2, except that starting material 2 was used instead of IMj-III, starting material 3 was used instead of 4-aminobiphenyl, starting material 4 was used instead of 4-bromobiphenyl, and the main starting materials used, the synthesized compounds and their final step yields and mass spectra were as shown in table 2.
TABLE 2
The nuclear magnetic data of a part of the compounds are shown in Table 3 below
TABLE 3 Table 3
Fabrication and evaluation examples of organic electroluminescent device
Example 1: manufacture of red organic electroluminescent device
The anode was prepared by the following procedure: sequentially the thickness isThe ITO/Ag/ITO substrate of (C) was cut into a size of 40mm (length). Times.40 mm (width). Times.0.7 mm (thickness), and a test substrate having anode and insulating layer patterns was prepared by a photolithography process using ultraviolet ozone and O 2 ∶N 2 The plasma is subjected to surface treatment to increase the work function of the anode 1, and the surface of the ITO substrate is cleaned by adopting an organic solvent to remove impurities and greasy dirt on the surface of the ITO substrate.
Vacuum evaporating m-MTDATA on experimental substrate to form a film with a thickness ofIs provided.
Vacuum evaporating HT-1 on the hole injection layer to form a film having a thickness ofIs provided.
Evaporating compound 2 on the first hole transport layer to form a film of thicknessIs provided.
On the second hole transport layer, CBP and Ir (piq) 2 (acac) vapor deposition at a vapor deposition rate ratio of 100:2 to form a thickness ofIs provided.
Evaporating ET-20 and LiQ on the organic light-emitting layer at an evaporation rate ratio of 1:1 to form a film with a thickness ofIs provided. Evaporating LiQ on the electron transport layer to form a film having a thickness +.>Electron injection layer of (a) is provided. Then, magnesium (Mg) and silver (Ag) are co-evaporated on the electron injection layer at an evaporation rate ratio of 1:9 to form a film having a thickness +.>Is provided.
In addition, the compound CP-1 is evaporated on the cathode to form a film with a thickness ofThereby completing the manufacture of the organic light emitting device.
Examples 2 to 34
An organic electroluminescent device was fabricated in the same manner as in example 1, except that the compound of table 4 was used instead of compound 2 in forming the second hole transport layer.
Comparative example 1-comparative example 3
An organic electroluminescent device was fabricated in the same manner as in example 1, except that compound a, compound B, and compound C were used instead of compound 2 in forming the second hole transport layer.
Wherein, in preparing the devices of the above examples and comparative examples, the structures of the compounds used are as follows:
performance test was performed on the red organic electroluminescent devices prepared in examples 1 to 34 and comparative examples 1 to 3, specifically at 10mA/cm 2 IVL performance of the device was tested at 20mA/cm 2 The test results are shown in table 4 below for T95 lifetime.
TABLE 4 Table 4
Referring to table 4 above, it can be seen that the device performance can be greatly improved when the compound of the present invention is used in the second hole transport layer of the red organic electroluminescent device. Specifically, the organic electroluminescent devices of examples 1 to 34 have improved current efficiency by at least 12.4% and improved T95 lifetime by at least 11% as compared to the organic electroluminescent devices of comparative examples 1 to 3.
The preferred embodiments of the present application have been described in detail above with reference to the accompanying drawings, but the present application is not limited to the specific details of the above embodiments, and various simple modifications may be made to the technical solutions of the present application within the scope of the technical concept of the present application, and all the simple modifications belong to the protection scope of the present application.
In addition, the specific features described in the foregoing embodiments may be combined in any suitable manner, and in order to avoid unnecessary repetition, various possible combinations are not described in detail.
Claims (13)
1. An organic compound, characterized in that the organic compound has a structure represented by formula I:
wherein R is 1 And R is 2 And are the same or different and are each independently selected from an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms or an aryl group having 6 to 18 carbon atoms, or R 1 And R is 2 The carbon atoms to which they are attached together form a saturated or unsaturated 3-to 15-membered ring;
each R is independently selected from deuterium, halogen group, cyano, trialkylsilyl with 3-10 carbon atoms, alkyl with 1-10 carbon atoms, halogenated alkyl with 1-10 carbon atoms, deuterated alkyl with 1-10 carbon atoms, aryl with 6-20 carbon atoms or heteroaryl with 3-20 carbon atoms;
n represents the number of R, n is selected from 0, 1,2, 3,4, 5 or 6;
L 1 and L 2 The same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar 1 and Ar is a group 2 Identical or different and are each independently selected from substituted or unsubstituted C6-C30 membersOr a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
L 1 、L 2 、Ar 1 and Ar is a group 2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano group, trialkylsilyl group having 3 to 10 carbon atoms, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuteroalkyl group having 1 to 10 carbon atoms, aryl group having 6 to 20 carbon atoms or heteroaryl group having 3 to 20 carbon atoms.
2. The organic compound according to claim 1, wherein R 1 And R is 2 Each independently selected from methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, tridentate methyl, phenyl, naphthyl or biphenyl, or R 1 And R is 2 The carbon atoms to which they are attached together form a cyclopentane, cyclohexane or fluorene ring.
3. The organic compound of claim 1, wherein each R is independently selected from deuterium, fluoro, cyano, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl.
4. The organic compound according to claim 1, wherein L 1 And L 2 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms;
alternatively, L 1 And L 2 The substituents in (a) are each independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, alkyl having 1 to 5 carbon atoms, or phenyl.
5. The organic compound according to claim 1, wherein L 1 And L 2 Each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, and a fetchSubstituted or unsubstituted biphenylene;
alternatively, L 1 And L 2 Each of the substituents is independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, methyl, ethyl, isopropyl, t-butyl, or phenyl.
6. The organic compound according to claim 1, wherein Ar 1 And Ar is a group 2 Each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms;
alternatively, ar 1 And Ar is a group 2 The substituents in (a) are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, alkyl having 1 to 5 carbon atoms, haloalkyl having 1 to 5 carbon atoms, deuterated alkyl having 1 to 5 carbon atoms, aryl having 6 to 12 carbon atoms, and heteroaryl having 5 to 12 carbon atoms.
7. The organic compound according to claim 1, wherein Ar 1 And Ar is a group 2 Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorene, substituted or unsubstituted cyclopentane spirofluorene, substituted or unsubstituted cyclohexane spirofluorene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, or substituted or unsubstituted carbazolyl;
alternatively, ar 1 And Ar is a group 2 Each of the substituents in (a) is independently selected from deuterium, fluoro, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, t-butyl, tridentate methyl or phenyl.
8. The organic compound according to claim 1, wherein Ar 1 And Ar is a group 2 Each independently selected from the group consisting of:
9. the organic compound according to claim 1, wherein,identical or different and are each independently selected from the group consisting of:
10. the organic compound according to claim 1, wherein the organic compound is selected from the group consisting of:
11. an electronic component, characterized in that the electronic component comprises an anode and a cathode which are oppositely arranged, and a functional layer arranged between the anode and the cathode; wherein the functional layer comprises the organic compound according to any one of claims 1 to 10.
12. The electronic element according to claim 11, wherein the functional layer includes a hole-transporting layer containing the organic compound;
optionally, the electronic element is an organic electroluminescent device or a photoelectric conversion device;
optionally, the organic electroluminescent device is a red organic electroluminescent device.
13. An electronic device, characterized in that it comprises an electronic component according to claim 11 or 12.
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