CN117327005A - Organic compound and organic electroluminescent device prepared from same - Google Patents
Organic compound and organic electroluminescent device prepared from same Download PDFInfo
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- CN117327005A CN117327005A CN202210725307.2A CN202210725307A CN117327005A CN 117327005 A CN117327005 A CN 117327005A CN 202210725307 A CN202210725307 A CN 202210725307A CN 117327005 A CN117327005 A CN 117327005A
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 35
- 238000002347 injection Methods 0.000 claims description 39
- 239000007924 injection Substances 0.000 claims description 39
- 125000001072 heteroaryl group Chemical group 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 34
- -1 dibenzofuranyl Chemical group 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
- 230000005525 hole transport Effects 0.000 claims description 27
- 230000000903 blocking effect Effects 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000001624 naphthyl group Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 238000006467 substitution reaction Methods 0.000 claims description 11
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 10
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 10
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 10
- 125000002541 furyl group Chemical group 0.000 claims description 10
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 10
- 125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- 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 9
- 125000006267 biphenyl group Chemical group 0.000 claims description 9
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- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
- 125000004431 deuterium atom Chemical group 0.000 claims description 8
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000005549 heteroarylene group Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000004957 naphthylene group Chemical group 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 5
- 125000005730 thiophenylene group Chemical group 0.000 claims description 5
- 229910052805 deuterium Inorganic materials 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical group [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
- 229960005235 piperonyl butoxide Drugs 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 81
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- 239000010410 layer Substances 0.000 description 138
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 239000000543 intermediate Substances 0.000 description 24
- 239000000758 substrate Substances 0.000 description 19
- 239000010408 film Substances 0.000 description 17
- 239000002994 raw material Substances 0.000 description 17
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 239000000741 silica gel Substances 0.000 description 13
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- 239000011368 organic material Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 10
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- 238000004809 thin layer chromatography Methods 0.000 description 8
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 8
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- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
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- 238000003786 synthesis reaction Methods 0.000 description 6
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- 230000000052 comparative effect Effects 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
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- 239000012046 mixed solvent Substances 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 238000002390 rotary evaporation Methods 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- 150000001616 biphenylenes Chemical group 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000005538 encapsulation Methods 0.000 description 3
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- 238000005286 illumination Methods 0.000 description 3
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 3
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 239000008204 material by function Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 238000007738 vacuum evaporation Methods 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
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OMDTUSYJJFBYMG-UHFFFAOYSA-N 2,4-bis(9,9-dimethylfluoren-2-yl)-6-naphthalen-2-yl-1,3,5-triazine Chemical compound C1=CC=C2C(C)(C)C3=CC(C=4N=C(N=C(N=4)C=4C=C5C=CC=CC5=CC=4)C4=CC=C5C6=CC=CC=C6C(C5=C4)(C)C)=CC=C3C2=C1 OMDTUSYJJFBYMG-UHFFFAOYSA-N 0.000 description 1
- UWRZIZXBOLBCON-UHFFFAOYSA-N 2-phenylethenamine Chemical class NC=CC1=CC=CC=C1 UWRZIZXBOLBCON-UHFFFAOYSA-N 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical compound N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 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
- 238000010521 absorption reaction Methods 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 150000001562 benzopyrans Chemical class 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 159000000006 cesium salts Chemical class 0.000 description 1
- AYTVLULEEPNWAX-UHFFFAOYSA-N cesium;azide Chemical compound [Cs+].[N-]=[N+]=[N-] AYTVLULEEPNWAX-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
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- 238000011161 development Methods 0.000 description 1
- 238000011982 device technology Methods 0.000 description 1
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- 229940058961 hydroxyquinoline derivative for amoebiasis and other protozoal diseases Drugs 0.000 description 1
- 150000002460 imidazoles Chemical class 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
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
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- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
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- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical compound [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- MESMXXUBQDBBSR-UHFFFAOYSA-N n,9-diphenyl-n-[4-[4-(n-(9-phenylcarbazol-3-yl)anilino)phenyl]phenyl]carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C4=CC=CC=C4N(C=4C=CC=CC=4)C3=CC=2)C=C1 MESMXXUBQDBBSR-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 150000004059 quinone derivatives Chemical class 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical class [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon 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
- 238000004528 spin coating Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 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
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000004017 vitrification Methods 0.000 description 1
- 238000005406 washing Methods 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
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
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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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Abstract
The invention discloses an organic compound and an organic electroluminescent device prepared from the same, which belong to the technical field of semiconductor materials.
Description
Technical Field
The invention relates to the technical field of semiconductor materials, in particular to an organic compound and an organic electroluminescent device prepared from the same.
Background
The organic electroluminescent (OLED: organic Light Emission Diodes) device technology can be used for manufacturing novel display products and novel illumination products, is hopeful to replace the existing liquid crystal display and fluorescent lamp illumination, and has wide application prospect. The OLED light-emitting device is like a sandwich structure and comprises electrode material film layers and organic functional materials clamped between the different electrode material film layers, wherein various different organic functional materials are mutually overlapped together according to purposes to jointly form the OLED light-emitting device. When voltage is applied to two end electrodes of the OLED light-emitting device as a current device, positive and negative charges in the organic layer functional material film layer act through an electric field, and the positive and negative charges are further compounded in the light-emitting layer, so that OLED electroluminescence is generated.
At present, the OLED display technology has been applied to the fields of smart phones, tablet computers and the like, and further expands to the large-size application fields of televisions and the like, but compared with the actual product application requirements, the OLED display technology has the advantages that the luminous efficiency, the service life and the like of the OLED device are further improved. The studies on the improvement of the performance of the OLED light emitting device include: the driving voltage of the device is reduced, the luminous efficiency of the device is improved, the service life of the device is prolonged, and the like. In order to realize the continuous improvement of the performance of the OLED device, not only is the innovation of the structure and the manufacturing process of the OLED device needed, but also the continuous research and innovation of the OLED photoelectric functional material are needed, and the functional material of the OLED with higher performance is created.
Blue organic electroluminescent devices are always soft ribs in full-color OLED development, so that the efficiency, service life and other performances of blue light devices are not fully improved until now, and therefore, how to improve the performances of the devices is still a critical problem and challenge in the field. Since the blue light host materials currently used in the market are mostly electron-biased host materials, the hole transport materials are required to have excellent hole transport properties in order to adjust the carrier balance of the light emitting layer. The better the hole injection and transmission, the more the adjusting composite area is deviated to the side far away from the electron blocking layer, so that the light is emitted far away from the interface, the performance of the device is improved, and the service life of the device is prolonged. Therefore, the hole transport region material is required to have high hole injection property, high hole mobility, high electron blocking property, and high electron weatherability.
In the prior art, in a high-temperature environment, as the difference between electron mobility and hole mobility is more obvious, a blue light device shows rich electrons and holes and has poor service life in the high-temperature environment, and in order to improve the high-temperature service life of the blue light device, the mobility of a hole transport material, especially the mobility under the high-temperature condition, needs to be improved.
Disclosure of Invention
In view of the above problems in the prior art, the applicant of the present invention provides an organic compound and an organic electroluminescent device prepared therefrom. The organic compound of the present invention has excellent hole transporting ability and thermal stability, and can simultaneously exhibit the effects of improving the efficiency (index) of the device and prolonging the life span, particularly prolonging the high temperature life span of the device, when the organic compound of the present invention is used to form a hole transporting material of an organic electroluminescent device.
The technical scheme of the invention is as follows: an organic compound, the structure of which is shown in a general formula (1):
in the general formula (1), A is represented by formula (3) or formula (4),
the B is represented by formula (2), formula (3) or formula (4);
the C is represented by a formula (2), a formula (3), a formula (4) or a hydrogen atom;
the R is 1 、R 2 、R 3 Represented independently as hydrogen atoms, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl; wherein R is 0 The substitution may be by bonding or by merging;
in the formula (2), the formula (3) and the formula (4), the curves represent the connection sites with the general formula (1);
the L, L 0 Represented by single bonds, substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted 5-30 membered heteroarylene;
the R is 0 Represented by hydrogen atoms, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl; wherein R is 0 The substitution may be by bonding or by merging;
the R is 4 、R 5 、R 6 Represented independently as substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl;
when A is represented by formula (3), R 1 、R 2 、R 3 Not simultaneously denoted as hydrogen atoms;
the substituents of the aforementioned substituted or unsubstituted groups are selected from deuterium atoms, methyl groups, deuterated methyl groups, ethyl groups, tertiary butyl groups, adamantyl groups, C 6 -C 30 Aryl or 5-30 membered heteroaryl;
the hetero atom in the heteroaryl is selected from one or more of oxygen atom, sulfur atom or nitrogen atom.
Preferably, the structure of the organic compound is shown as a general formula (1-1), a general formula (1-2), a general formula (1-3) and a general formula (1-4):
in the general formula (1-1), the C is represented by a formula (2), a formula (3), a formula (4) or a hydrogen atom;
The L, L 0 Represented by single bonds, substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted 5-30 membered heteroarylene;
the R is 0 Represented independently as hydrogen atoms, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl; wherein R is 0 The substitution may be by bonding orAnd (3) ring combining;
the R is 1 、R 2 、R 3 Represented independently as hydrogen atoms, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl;
the R is 1 、R 2 、R 3 Not simultaneously denoted as hydrogen atoms;
the R is 5 、R 6 Represented independently as substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl;
in the general formula (1-2) and the general formula (1-3), L and L 0 Represented by single bonds, substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted 5-30 membered heteroarylene;
the R is 0 、R 1 、R 2 、R 3 Represented independently as hydrogen atoms, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl; wherein R is 0 The substitution may be by bonding or by merging;
the R is 5 、R 6 Represented independently as substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl;
in the general formula (1-4), L represents a single bond, a substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted 5-30 membered heteroarylene;
The R is 1 、R 2 、R 3 Represented independently as hydrogen atoms, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl; wherein R is 0 The substitution may be by bonding or by merging;
the R is 4 、R 5 、R 6 Represented independently as substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl;
the substituents of the aforementioned substituted or unsubstituted groups are selected from deuterium atoms, methyl groups, deuterated methyl groups, ethyl groupsRadical, tert-butyl, adamantyl, C 6 -C 30 Aryl or 5-30 membered heteroaryl;
the hetero atom in the heteroaryl is selected from one or more of oxygen atom, sulfur atom or nitrogen atom.
Preferably, the structure of the organic compound is shown as a general formula (1-5), a general formula (1-6), a general formula (1-7) and a general formula (1-8):
in the general formula (1-5), the R 3 Represented as substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl, said R 0 、R 5 、R 6 L, L 0 The meaning of (2) is as described above;
in the general formulae (1-6) and (1-7), R is 3 Represented by hydrogen atoms, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl, said R 0 、R 5 、R 6 L, L 0 The meaning of (2) is as described above;
in the general formula (1-8), R 2 、R 3 Represented independently as hydrogen atoms, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl, said R 4 、R 5 、R 6 The meaning of L is as described above.
Preferably, the structure of the organic compound is shown as a general formula (1-9), a general formula (1-10), a general formula (1-11) and a general formula (1-12):
in the general formula (1-9), the L 0 L is independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted furanylene group, a substituted or unsubstituted thioylene groupA phenone group;
the R is 3 Represented as one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted piperonyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted carbazolyl group, and a substituted or unsubstituted N-phenylcarbazolyl group;
The R is 5 -R 6 Represented independently as substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl;
in the general formula (1-10), the general formula (1-11) and the general formula (1-12), L 0 L is independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted furanylene group, a substituted or unsubstituted thiophenylene group;
the R is 3 Represented as one of a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted piperonyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted carbazolyl group, and a substituted or unsubstituted N-phenylcarbazolyl group;
the R is 4 Represented by a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted Substituted or unsubstituted furyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted thienyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted indenyl, substituted or unsubstituted piperonyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl;
the R is 5 -R 6 Represented independently as substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl;
the substituent of the substituted or substituted group is selected from one or more of deuterium atom, methyl, deuterated methyl, ethyl, tertiary butyl, adamantyl, phenyl, naphthyl and biphenyl.
Preferably, the L 0 L is independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted furanylene group, a substituted or unsubstituted thiophenylene group;
the R is 0 、R 1 、R 2 、R 3 One of a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted piperonyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group;
The R is 4 、R 5 、R 6 Represented as substitution orAn unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted piperonyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group;
the substituent of the substituted or substituted group is selected from one or more of deuterium atom, methyl, deuterated methyl, ethyl, tertiary butyl, adamantyl, phenyl, naphthyl and biphenyl.
Preferably, the formula (2) is represented by any one of the following structures:
the formula (3) is represented by any one of the following structures:
the formula (4) is represented by any one of the following structures:
preferably, the specific structure of the organic compound is any one of the following structures:
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The invention provides an organic electroluminescent device which sequentially comprises an anode, a hole transport region, a light emitting region, an electron transport region and a cathode, wherein the hole transport region comprises the organic compound.
Preferably, the hole transport region of the organic electroluminescent device includes a hole injection layer, a hole transport layer, and an electron blocking layer, and the hole transport layer includes the organic compound.
The invention provides an illumination or display element comprising the organic electroluminescent device.
The beneficial technical effects of the invention are as follows:
(1) The organic compound has better dispersivity of the whole molecule and wider HOMO distribution, which is beneficial to improving hole mobility, promoting the transmission effect on holes, effectively improving the efficiency of the device and reducing the voltage of the device.
(2) The structural characteristics of the organic compound are favorable for reducing the interaction force among molecules, so that the vapor deposition temperature of the molecules is reduced, that is, even though the molecular weight of the structure is relatively high, the organic compound can ensure that the organic compound has relatively low vapor deposition temperature, and the excellent performance is not only favorable for thermal vapor deposition of materials, but also controls the thermal decomposition rate of the materials, so that the stability of the materials in device application is improved.
(3) Meanwhile, the structural characteristics can raise the vitrification transfer temperature of molecules, so that the stability of a film phase state is ensured, and the stability of the film phase state under the lighting condition is further favorable for obtaining the service life stability of a device.
Drawings
Fig. 1 is a cross-sectional view of an organic electroluminescent device according to the present invention.
In the figure, 1 represents a substrate layer; 2 represents an anode layer; 3 represents a hole injection layer; 4 represents a hole transport layer; 5 represents an electron blocking layer; 6 represents a light emitting layer; 7 represents a hole blocking layer; 8 represents an electron transport layer; 9 denotes an electron injection layer; 10 is denoted as cathode layer; 11 denotes a cover layer.
Detailed Description
The following description of the embodiments of the present invention will be made clearly and completely with reference to the accompanying drawings, in which it is apparent that the embodiments described are only some embodiments of the present invention, but not all embodiments. The following description of at least one exemplary embodiment is merely exemplary in nature and is in no way intended to limit the invention, its application, or uses. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
In the present invention, when a layer or element is referred to as being "on" another layer or substrate, it can be directly on the other layer or substrate or intervening layers may also be present. Further, it will also be understood that when a layer is referred to as being "between" two layers, it can be the only layer between the two layers or one or more intervening layers may also be present. Like numbers refer to like elements throughout.
In the present invention, when describing electrodes and organic electroluminescent devices, as well as other structures, words of "upper", "lower", "top" and "bottom", etc., which are used to indicate orientations, indicate only orientations in a certain specific state, and do not mean that the relevant structure can only exist in the orientations; conversely, if the structure can be repositioned, for example inverted, the orientation of the structure is changed accordingly. Specifically, in the present invention, the "bottom" side of an electrode refers to the side of the electrode that is closer to the substrate during fabrication, while the opposite side that is farther from the substrate is the "top" side.
In this specification, the term "substituted" means that one or more hydrogen atoms on a given atom or group is replaced by the specified group, provided that the normal valence of the given atom is not exceeded in the present case.
In this specification, the hole feature refers to a feature that can supply electrons when an electric field is applied and is attributed to a conductive feature according to the Highest Occupied Molecular Orbital (HOMO) level, and holes formed in the anode are easily injected into and transported in the light emitting layer.
In this specification, the electron feature refers to a feature that can accept electrons when an electric field is applied and is attributed to a conductive feature according to the Lowest Unoccupied Molecular Orbital (LUMO) level, electrons formed in the cathode are easily injected into and transported in the light emitting layer.
The organic electroluminescent device of the present invention may be a bottom-emission organic electroluminescent device, a top-emission organic electroluminescent device, and a stacked organic electroluminescent device, and is not particularly limited.
In the organic electroluminescent device of the present invention, any substrate commonly used for organic electroluminescent devices may also be used. Examples thereof are transparent substrates such as glass or transparent plastic substrates; an opaque substrate such as a silicon substrate; a flexible Polyimide (PI) film substrate. Different substrates have different mechanical strength, thermal stability, transparency, surface smoothness, and water repellency. The use direction of the substrate is different according to the property of the substrate. In the present invention, a transparent substrate is preferably used. The thickness of the substrate is not particularly limited.
Anode
Preferably, the anode may be formed on the substrate. In the present invention, the anode and the cathode are opposite to each other. The anode may be made of a conductor having a higher work function to aid hole injection, and may be, for example, a metal such as nickel, platinum, copper, zinc, silver, or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combinations of metals and metal oxides, such as ZnO with Al or ITO with Ag; conductive polymers such as poly (3-methylthiophene), poly (3, 4- (ethylene-1, 2-dioxy) thiophene), and polyaniline, but are not limited thereto. The thickness of the anode depends on the material used, and is generally 50 to 500nm, preferably 70 to 300nm, and more preferably 100 to 200nm.
Cathode electrode
The cathode may be made of a conductor having a lower work function to aid electron injection, and may be, for example, a metal or an alloy thereof, such as magnesium, calcium, sodium, potassium, titanium, indium, aluminum, silver, tin, and combinations thereof; multilayer structural materials, such as LiF/Al, li 2 O/Al and BaF 2 /Ca, but is not limited thereto. The thickness of the cathode is generally 10-50nm, preferably 15-20nm, depending on the material used.
Light emitting region
In the present invention, the light emitting region may be disposed between the anode and the cathode, and may include at least one host material and at least one guest material. As the host material and the guest material of the light-emitting region of the organic electroluminescent device of the present invention, a light-emitting layer material for an organic electroluminescent device known in the art can be used. The host material may be, for example, a thiazole derivative, a benzimidazole derivative, a polydialkylfluorene derivative, or 4,4' -bis (9-Carbazolyl) Biphenyl (CBP). As host material, compounds containing anthracene groups can be used. The guest material may be, for example, quinacridone, coumarin, rubrene, perylene and derivatives thereof, benzopyran derivatives, rhodamine derivatives or aminostyrene derivatives.
In a preferred embodiment of the invention, one or two host material compounds are contained in the light-emitting region.
In a preferred embodiment of the invention, the host material of the light-emitting region used is selected from one or more of the following compounds BH-1-BH-11:
in the present invention, the light emitting region may include a phosphorescent or fluorescent guest material to improve fluorescence or phosphorescence characteristics of the organic electroluminescent device. Specific examples of the phosphorescent guest material include metal complexes of iridium, platinum, and the like, and as the fluorescent guest material, those generally used in the art can be used. In a preferred embodiment of the present invention, the guest material of the light-emitting film layer used is selected from one of the following compounds BD-1 to BD-10:
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in the light-emitting region of the present invention, the ratio of host material to guest material used is 99:1 to 70:30, preferably 99:1 to 85:15 and more preferably 97:3 to 87:13 on a mass basis.
The thickness of the light emitting region may be 10 to 50nm, preferably 15 to 30nm, but the thickness is not limited to this range.
Hole transport region
In the organic electroluminescent device of the present invention, a hole transport region is disposed between the anode and the light emitting region, and includes a hole injection layer, a hole transport layer, and an electron blocking layer.
Hole injection layer
The hole injection material used in the hole injection layer (also referred to as an anode interface buffer layer) is a material capable of sufficiently accepting holes from the anode at a low voltage, and the Highest Occupied Molecular Orbital (HOMO) of the hole injection material is preferably a value between the work function of the anode material and the HOMO of the adjacent organic material layer. In a preferred embodiment of the present invention, the hole injection layer is a mixed film of host organic material and P-type dopant material. In order to enable holes to be smoothly injected into the organic film layer from the anode, the HOMO energy level of the main organic material and the P-type doping material must have certain characteristics, so that the occurrence of a charge transfer state between the main material and the doping material is expected to be realized, ohmic contact between the hole injection layer and the anode is realized, and efficient injection of holes from the electrode to the hole injection layer is realized. This feature is summarized as: the difference between the HOMO energy level of the host material and the LUMO energy level of the P-type doped material is less than or equal to 0.4eV. Therefore, for hole host materials with different HOMO energy levels, different P-type doping materials are required to be selected to be matched with the hole host materials, so that ohmic contact of an interface can be realized, and the hole injection effect is improved.
Preferably, specific examples of the host organic material include: metalloporphyrin, oligothiophene, arylamine organic materials, hexanitrile hexaazabenzophenanthrene, quinacridone organic materials, perylene organic materials, anthraquinone, polyaniline and polythiophene conductive polymers; but is not limited thereto.
Preferably, the P-type dopant material is a compound having charge conductivity selected from the group consisting of: quinone derivatives or metal oxides such as tungsten oxide and molybdenum oxide, but are not limited thereto.
In a preferred embodiment of the invention, the P-type doping material used is selected from any of the following compounds P-1 to P-8:
in one embodiment of the invention, the ratio of host organic material to P-type dopant material used is 99:1 to 95:5, preferably 99:1 to 97:3, on a mass basis.
In a preferred embodiment of the present invention, the hole injection layer is a mixed film layer of the organic compound of the present invention and the P-type dopant material.
The thickness of the hole injection layer of the present invention may be 5 to 20nm, preferably 8 to 15nm, but the thickness is not limited to this range.
Hole transport layer
In the organic electroluminescent device of the present invention, a hole transport layer may be disposed over the hole injection layer. The hole transport material is suitably a material having a high hole mobility, which can accept holes from the anode or the hole injection layer and transport the holes into the light emitting layer. In a preferred embodiment, the hole transport layer comprises the same organic compound of the present invention represented by the general formula (1) as the hole injection layer.
The thickness of the hole transport layer of the present invention may be 80, 100 or 200nm, preferably 100 to 150nm, but the thickness is not limited to this range.
Electron blocking layer
In the organic electroluminescent device of the present invention, an electron blocking layer may be disposed between the hole transport layer and the light emitting layer, and particularly contact the light emitting layer. The electron blocking layer is disposed to contact the light emitting layer, and thus, hole transfer at the interface of the light emitting layer and the hole transporting layer can be precisely controlled. In one embodiment of the invention, the electron blocking layer material is selected from carbazole-based aromatic amine derivatives. The thickness of the electron blocking layer may be 5 to 20nm, preferably 8 to 15nm, but the thickness is not limited to this range.
Electron transport region
In the organic electroluminescent device of the present invention, an electron transport region is disposed between the light emitting region and the cathode, and includes a hole blocking layer, an electron transport layer, and an electron injection layer, but is not limited thereto.
Electron injection layer
The electron injection layer may be disposed between the electron transport layer and the cathode. The electron injection layer material is generally a material preferably having a low work function so that electrons are easily injected into the organic functional material layer. Preferably, the electron injection layer material is an N-type metal material. As the electron injection layer material of the organic electroluminescent device of the present invention, electron injection layer materials for organic electroluminescent devices known in the art, for example, lithium; lithium salts such as lithium 8-hydroxyquinoline, lithium fluoride, lithium carbonate or lithium azide; or cesium salts, cesium fluoride, cesium carbonate or cesium azide. The thickness of the electron injection layer of the present invention may be 0.1 to 5nm, preferably 0.5 to 3nm, and more preferably 0.8 to 1.5nm, but the thickness is not limited to this range.
Electron transport layer
The electron transport layer may be disposed over the light emitting film layer or (if present) the hole blocking layer. The electron transport layer material is a material that easily receives electrons of the cathode and transfers the received electrons to the light emitting layer. Materials with high electron mobility are preferred. Examples of the electron transport layer material used for the organic electroluminescent device of the present invention include metal complexes of hydroxyquinoline derivatives such as Alq3, BAlq and LiQ, various rare earth metal complexes, triazole derivatives, triazine derivatives such as 2, 4-bis (9, 9-dimethyl-9H-fluoren-2-yl) -6- (naphthalen-2-yl) -1,3, 5-triazine (CAS. RTM. 1459162-51-6), and imidazole derivatives such as 2- (4- (9, 10-bis (naphthalen-2-yl) anthracene-2-yl) phenyl) -1-phenyl-1H-benzo [ d ] imidazole (CAS. RTM. 561064-11-7, commonly referred to as LG 201), and the like.
In a preferred embodiment of the invention, the electron transport layer also comprises other compounds conventionally used in electron transport layers, for example Alq3, liQ, preferably LiQ.
The thickness of the electron transport layer of the present invention may be 10 to 80nm, preferably 20 to 60nm, and more preferably 25 to 45nm, but the thickness is not limited to this range.
Cover layer
In order to improve the light-emitting efficiency of the organic electroluminescent device, a light extraction layer (i.e., a CPL layer, also referred to as a capping layer) may be further added to the cathode of the device. According to the optical absorption and refraction principles, the higher the refractive index of the CPL cover layer material is, the better the CPL cover layer material is, and the smaller the light absorption coefficient is, the better the CPL cover layer material is. Any material known in the art may be used as the CPL layer material, such as Alq3, or N4, N4' -diphenyl-N4, N4' -bis (9-phenyl-3-carbazolyl) biphenyl-4, 4' -diamine. The CPL coating typically has a thickness of 5-300nm, preferably 20-100nm and more preferably 40-80nm.
The organic electroluminescent device of the present invention may further include an encapsulation structure. The encapsulation structure may be a protective structure that prevents foreign substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device. The encapsulation structure may be, for example, a can, such as a glass can or a metal can; or a thin film covering the entire surface of the organic layer.
The method of manufacturing an organic electroluminescent device according to the present invention comprises sequentially laminating an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an organic film layer, an electron transport layer, an electron injection layer, and a cathode, and optionally a capping layer, on a substrate. In this regard, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, or LITI may be used, but are not limited thereto. In the present invention, the respective layers are preferably formed by a vacuum vapor deposition method. The individual process conditions in the vacuum evaporation process can be routinely selected by those skilled in the art according to the actual needs.
Synthetic examples
Example 1: synthesis of intermediate K-1
Step (1)
Step (2)
(1) In a three-necked flask, under the protection of nitrogen, 0.01mol of raw material A-1,0.012mol of raw material B-1 and 150ml of toluene are added and mixed under stirring, and then 5X 10 is added -5 mol Pd 2 (dba) 3 ，5×10 -5 Heating 0.03mol of tri-tert-butyl phosphorus and 0.03mol of sodium tert-butoxide to 105 ℃, and carrying out reflux reaction for 18 hours, wherein a sampling point plate shows that no amino compound remains and the reaction is complete; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction is present, and passing through neutral silica gel column to obtain intermediate C-1.
(2) Under nitrogen atmosphere, 0.06mol of intermediate C-1 was added to a three-necked flask, and a mixed solvent (300 ml of toluene, 90ml of H was added 2 O) dissolving it, stirring for 1 hr under nitrogen, and slowly adding 0.05mol of raw material D-1 and 0.1mol of K 2 CO 3 、0.005mol Pd(PPh 3 ) 4 The reaction was heated to 90℃and observed by Thin Layer Chromatography (TLC) for 8 hours until the reaction was complete. Naturally cooling to room temperature, adding water into the reaction system for extraction, separating liquid, and performing reduced pressure rotary evaporation on the organic phase until no fraction exists. The obtained material was purified by silica gel column to obtain intermediate K-1.
Example 2: synthesis of intermediate K-2
Step (1)
Into a three-necked flask, 0.01mol of intermediate K-1, 0.02mol of pinacol biborate (raw material N), 0.03mol of potassium acetate and 5X 10 were successively introduced -5 mol Pd(dppf)Cl 2 100mL of 1, 4-dioxane is stirred and mixed, heated to 80 ℃ and reacted for 6 hours, a spot plate is sampled, no intermediate K-1 remains, and the reaction is complete; naturally cooling to room temperature, adding water, precipitating solid, filtering, taking a filter cake, drying by a vacuum drying oven, and then passing through a neutral silica gel column to obtain a borate compound intermediate S-1.
Step (2)
Under nitrogen atmosphere, 0.06mol of raw material B-2 was charged into a three-necked flask, and a mixed solvent (300 ml of toluene, 90ml of H was added 2 O) dissolving it, stirring for 1 hour by introducing nitrogen, then slowly adding 0.05mol of intermediate S-1 and 0.1mol of K 2 CO 3 、0.005mol Pd(PPh 3 ) 4 The reaction was heated to 90℃and observed by Thin Layer Chromatography (TLC) for 8 hours until the reaction was complete. Naturally cooling to room temperature, adding water into the reaction system for extraction, separating liquid, and performing reduced pressure rotary evaporation on the organic phase until no fraction exists. The obtained material was purified by silica gel column to obtain intermediate K-2.
The following intermediates were prepared in a similar manner to that in example 1, table 1 below
TABLE 1
Example 2: synthesis of intermediate K-4
In a three-necked flask, under the protection of nitrogen, 0.024mol of raw material A-1,0.01mol of raw material B-3 and 150ml of toluene were added and mixed under stirring, and then 5X 10 was added -5 mol Pd 2 (dba) 3 ，5×10 -5 Heating 0.03mol of tri-tert-butyl phosphorus and 0.03mol of sodium tert-butoxide to 105 ℃, and carrying out reflux reaction for 20 hours, wherein a sampling point plate shows that no amino compound remains and the reaction is complete; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction exists, and passing through a neutral silica gel column to obtain an intermediate K-4.
Example 3: synthesis of Compound 1
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Adding 0.01mol of raw material E-1,0.012mol of intermediate K-1 and 150ml of toluene into a three-port bottle under the protection of nitrogen, stirring and mixing, then adding 5X 10-5mol of Pd2 (dba) 3, 5X 10-5mol of tri-tert-butyl phosphorus and 0.03mol of sodium tert-butoxide, heating to 105 ℃, carrying out reflux reaction for 24 hours, sampling a dot plate, and displaying no amino compound to remain, wherein the reaction is complete; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction exists, and passing through a neutral silica gel column to obtain the compound 1. Elemental analysis structure (molecular formula C) 50 H 44 N 2 ): test value: c,89.24; h,6.56; n,4.19.LC-MS: measurement value: 673.48 ([ M+H)]+)。
The following compounds were prepared in a similar manner as in example 3, table 2 below:
TABLE 2
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Example 4: synthesis of Compound 179
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In a three-necked flask, under the protection of nitrogen, 0.01mol of raw material A-1,0.012mol of raw material B-4 and 150ml of toluene are added and mixed under stirring, and then 5X 10 is added -5 mol Pd 2 (dba) 3 ，5×10 -5 Heating 0.03mol of tri-tert-butyl phosphorus and 0.03mol of sodium tert-butoxide to 105 ℃, carrying out reflux reaction for 17 hours, and taking a sample from a spot plate to show that no amino compound remains and the reaction is complete; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction is present, and passing through a neutral silica gel column to obtain an intermediate C-2.
In a three-necked flask, under the protection of nitrogen, 0.01mol of raw material F-1,0.012mol of intermediate C-2 and 150ml of toluene are added and stirred and mixed, and then 5X 10 is added -5 mol Pd 2 (dba) 3 ，5×10 -5 Heating 0.03mol of tri-tert-butyl phosphorus and 0.03mol of sodium tert-butoxide to 105 ℃, and carrying out reflux reaction for 18 hours, wherein a sampling point plate shows that no amino compound remains and the reaction is complete; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction exists, and passing through a neutral silica gel column to obtain an intermediate M-1.
In a three-necked flask, under the protection of nitrogen, 0.01mol of raw material E-8,0.012mol of intermediate M-1 and 150ml of toluene are added and stirred and mixed, and then 5X 10 is added -5 mol Pd 2 (dba) 3 ，5×10 -5 mol of tri-tert-butyl phosphorus, 0.03mol of sodium tert-butoxide, heating to 110 ℃, carrying out reflux reaction for 22 hours, sampling a dot plate, and displaying no amino compoundThe residual substances are reacted completely; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction exists, and passing through a neutral silica gel column to obtain the compound 179. Elemental analysis structure (molecular formula C) 63 H 51 N 3 ): test value: c,89.05; h,6.03; n,4.91.LC-MS: measurement value: 850.33 ([ M+H)]+)。
The following compounds are prepared in a similar manner to that of example 4 as shown in Table 3 below, wherein starting materials A-1 and B-4 are all the same as in example 4.
TABLE 3 Table 3
Example 5: synthesis of Compound 248
Step (1)
Step (2)
Step (3)
Step (4)
(1) Adding 0.01mol of raw material A-2,0.012mol of raw material B-5 and 150ml of toluene into a three-necked flask under the protection of nitrogen, stirring and mixing, and then adding 5X 10 -5 mol Pd 2 (dba) 3 ，5×10 -5 Heating 0.03mol of tri-tert-butyl phosphorus and 0.03mol of sodium tert-butoxide to 105 ℃, and carrying out reflux reaction for 20 hours, wherein a sampling point plate shows that no amino compound remains and the reaction is complete; naturally coolingCooling to room temperature, filtering, steaming the filtrate until no fraction exists, and passing through a neutral silica gel column to obtain an intermediate P-1.
(2) Under nitrogen atmosphere, 0.06mol of raw material H-1 was charged into a three-necked flask, and a mixed solvent (300 ml of toluene, 90ml of H was added 2 O) dissolving it, stirring for 1 hour by introducing nitrogen, then slowly adding 0.05mol of intermediate P-1 and 0.1mol of K 2 CO 3 、0.005mol Pd(PPh 3 ) 4 The reaction was heated to 90℃and observed by Thin Layer Chromatography (TLC) for 8 hours until the reaction was complete. Naturally cooling to room temperature, adding water into the reaction system for extraction, separating liquid, and performing reduced pressure rotary evaporation on the organic phase until no fraction exists. The obtained material was purified by silica gel column to obtain intermediate R-1.
(3) Under nitrogen atmosphere, 0.06mol of raw material D-1 was charged into a three-necked flask, and a mixed solvent (300 ml of toluene, 90ml of H was added 2 O) dissolving it, stirring for 1 hr with nitrogen, then slowly adding 0.05mol of intermediate R-1, 0.1mol of K 2 CO 3 、0.005mol Pd(PPh 3 ) 4 The reaction was heated to 90℃and was observed by Thin Layer Chromatography (TLC) for 10 hours until the reaction was complete. Naturally cooling to room temperature, adding water into the reaction system for extraction, separating liquid, and performing reduced pressure rotary evaporation on the organic phase until no fraction exists. The resulting material was purified by silica gel column to give intermediate J-1.
(4) In a three-necked flask, under the protection of nitrogen, 0.01mol of raw material E-9,0.012mol of intermediate J-1 and 150ml of toluene were added and mixed under stirring, and then 5X 10 was added -5 mol Pd 2 (dba) 3 ，5×10 -5 Heating 0.03mol of tri-tert-butyl phosphorus and 0.03mol of sodium tert-butoxide to 105 ℃, and carrying out reflux reaction for 23 hours, wherein a sampling point plate shows that no amino compound remains and the reaction is complete; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction exists, and passing through a neutral silica gel column to obtain a compound 248. Elemental analysis structure (molecular formula C) 56 H 48 N 2 ): test value: c,89.83; h,6.47; n,3.71.LC-MS: measurement value: 749.14 ([ M+H)]+)。
The following compounds were prepared in a similar manner to that in example 5, as shown in Table 4 below, with the starting material H-1 used in step (2) unchanged and not given in the following table.
TABLE 4 Table 4
Preparation of organic electroluminescent device
The molecular structural formula of the materials involved in the following preparation process is shown as follows:
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device comparative example 1
The organic electroluminescent device is prepared according to the following steps:
as shown in fig. 1, the substrate layer 1 is transparent glass, and the anode layer 2 (Ag (100 nm)) is washed, that is, sequentially alkali-washed, pure water-washed, dried, and then ultraviolet-ozone-washed to remove organic residues on the surface of the anode layer. On the anode layer 2 after the above washing, HT-1 and P-1 having film thicknesses of 10nm were vapor deposited as hole injection layers 3 by a vacuum vapor deposition apparatus, and the mass ratio of HT-1 and P-1 was 97:3. Next, HT-1 was evaporated to a thickness of 117nm as a hole transport layer 4. Subsequently EB-1 was evaporated to a thickness of 10nm as an electron blocking layer 5. After the evaporation of the electron blocking material is completed, a light emitting layer 6 of the OLED light emitting device is manufactured, and the structure of the light emitting layer comprises BH-1 used by the OLED light emitting layer 6 as a main material, BD-1 as a doping material, the doping material doping ratio is 3% by weight, and the film thickness of the light emitting layer is 20nm. After the light-emitting layer 6 was deposited, HB-1 was further deposited to a thickness of 8nm as a hole blocking layer 7. And (3) continuously evaporating ET-1 and Liq on the hole blocking layer 7, wherein the mass ratio of the ET-1 to the Liq is 1:1. The vacuum deposition film thickness of the material is 30nm, and the layer is an electron transport layer 8. On the electron transport layer 8, a LiF layer having a film thickness of 1nm, which is an electron injection layer 9, was formed by a vacuum vapor deposition apparatus. On the electron injection layer 9, mg having a film thickness of 16nm was produced by a vacuum vapor deposition apparatus: the mass ratio of Mg to Ag in the Ag electrode layer is 1:9, and the Ag electrode layer is used as the cathode layer 10. On the cathode layer 10, 65nm of CP-1 was vacuum-deposited as CPL layer 11.
Device comparative examples 2 to 6
The procedure of device comparative example 1 was conducted except that the organic materials in the hole injection layer and the hole transport layer were replaced with the organic materials shown in table 5, respectively.
Device examples 1 to 19
The procedure of device comparative example 1 was conducted except that the organic materials in the hole injection layer and the hole transport layer were replaced with the organic materials shown in table 5, respectively.
TABLE 5
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Taking example 1 row as an example in the table above, the "P-1:1=3:9710 nm" in the second column table indicates that the hole injection layer uses the compound 1 and the P-type doping material P-1, and the weight ratio of the P-type doping material to the compound 1 is 3:9710nm represents the thickness of the layer; the third column of the tables, "1117nm" indicates that the material used is compound 1 and the layer thickness is 117nm. And so on in other tables.
After the OLED light-emitting device was fabricated as described above, the cathode and anode were connected using a well-known driving circuit, and various properties of the device were measured.
The results of measuring the performance of the devices of examples 1 to 19 and comparative examples 1 to 6 are shown in Table 6.
TABLE 6
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Note that: the voltage, current efficiency and color coordinates were tested using an IVL (Current-Voltage-Brightness) test system (Freund's scientific instruments, st. John) with a current density of 10mA/cm 2 The method comprises the steps of carrying out a first treatment on the surface of the The life test system is an EAS-62C OLED device life tester of Japanese system technical research company; LT95 refers to the time taken for the device brightness to decay to 95% at a particular brightness; the high temperature lifetime test temperature is 85 ℃, LT80 refers to the time taken for the device brightness to decay to 80% at a particular brightness.
As can be seen from the results of table 6, the use of the organic compound of the present invention as a hole transport layer material effectively improves device efficiency and device lifetime, particularly device efficiency and high temperature lifetime, due to the higher carrier transport rate.
Claims (10)
1. An organic compound is characterized in that the structure of the organic compound is shown as a general formula (1):
in the general formula (1), A is represented by formula (3) or formula (4);
the B is represented by formula (2), formula (3) or formula (4);
the C is represented by a formula (2), a formula (3), a formula (4) or a hydrogen atom;
the R is 1 、R 2 、R 3 Represented independently as hydrogen atoms, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl; wherein R is 0 The substitution may be by bonding or by merging;
in the formula (2), the formula (3) and the formula (4), the curves represent the connection sites with the general formula (1);
the above-mentioned group of compounds is represented by the formula L,L 0 represented by single bonds, substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted 5-30 membered heteroarylene;
the R is 0 Represented by hydrogen atoms, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl; wherein R is 0 The substitution may be by bonding or by merging;
the R is 4 、R 5 、R 6 Represented independently as substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl;
when A is represented by formula (3), R 1 、R 2 、R 3 Not simultaneously denoted as hydrogen atoms;
the substituents of the aforementioned substituted or unsubstituted groups are selected from deuterium atoms, methyl groups, deuterated methyl groups, ethyl groups, tertiary butyl groups, adamantyl groups, C 6 -C 30 Aryl or 5-30 membered heteroaryl;
the hetero atom in the heteroaryl is selected from one or more of oxygen atom, sulfur atom or nitrogen atom.
2. The organic compound according to claim 1, wherein the structure of the organic compound is represented by general formula (1-1), general formula (1-2), general formula (1-3), general formula (1-4):
in the general formula (1-1), the C is represented by a formula (2), a formula (3), a formula (4) or a hydrogen atom;
the L, L 0 Represented by single bonds, substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted 5-30 membered heteroarylene;
the R is 0 Represented independently as hydrogen atoms, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl; wherein R is 0 The substitution may be by bonding or by merging;
the R is 1 、R 2 、R 3 Represented independently as hydrogen atoms, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl;
the R is 1 、R 2 、R 3 Not simultaneously denoted as hydrogen atoms;
the R is 5 、R 6 Represented independently as substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl;
in the general formula (1-2) and the general formula (1-3), L and L 0 Represented by single bonds, substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted 5-30 membered heteroarylene;
the R is 0 、R 1 、R 2 、R 3 Represented independently as hydrogen atoms, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl; wherein R is 0 The substitution may be by bonding or by merging;
the R is 5 、R 6 Represented independently as substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl;
in the general formula (1-4), L represents a single bond, a substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted 5-30 membered heteroarylene;
the R is 1 、R 2 、R 3 Represented independently as hydrogen atoms, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl; wherein R is 0 The substitution may be by bonding or by merging;
The R is 4 、R 5 、R 6 Represented independently as substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl;
the substituents of the aforementioned substituted or unsubstituted groups are selected from deuterium atoms, methyl groups, deuterated methyl groups, ethyl groups, tertiary butyl groups, adamantyl groups, C 6 -C 30 Aryl or 5-30 membered heteroaryl;
the hetero atom in the heteroaryl is selected from one or more of oxygen atom, sulfur atom or nitrogen atom.
3. The organic compound according to claim 1, wherein the structure of the organic compound is represented by general formula (1-5), general formula (1-6), general formula (1-7), general formula (1-8):
in the general formula (1-5), the R 3 Represented as substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl, said R 0 、R 5 、R 6 L, L 0 The meaning of (1) is as defined in claim 1;
in the general formulae (1-6) and (1-7), R is 3 Represented by hydrogen atoms, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl, said R 0 、R 5 、R 6 L, L 0 The meaning of (1) is as defined in claim 1;
in the general formula (1-8), R 2 、R 3 Represented independently as hydrogen atoms, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl, said R 4 、R 5 、R 6 The meaning of L is as defined in claim 1.
4. The organic compound according to claim 1, wherein the structure of the organic compound is represented by general formula (1-9), general formula (1-10), general formula (1-11), general formula (1-12):
In the general formula (1-9), the L 0 L is independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted furanylene group, a substituted or unsubstituted thiophenylene group;
the R3 is one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted furyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted indenyl, substituted or unsubstituted piperonyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted carbazolyl and substituted or unsubstituted N-phenylcarbazolyl;
the R is 5 -R 6 Represented independently as substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl;
in the general formula (1-10), the general formula (1-11) and the general formula (1-12), L 0 L is independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted furanylene group, a substituted or unsubstituted thiophenylene group;
The R is 3 Represented by a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted benzofuranyl group,One of a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted piperonyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group;
the R is 4 Represented as one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted piperonyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted carbazolyl group, and a substituted or unsubstituted N-phenylcarbazolyl group;
The R is 5 -R 6 Represented independently as substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl;
the substituent of the substituted or substituted group is selected from one or more of deuterium atom, methyl, deuterated methyl, ethyl, tertiary butyl, adamantyl, phenyl, naphthyl and biphenyl.
5. The organic compound according to any one of claims 1 to 4, wherein L 0 L is independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted furanylene group, a substituted or unsubstituted thiophenylene group;
the R is 0 、R 1 、R 2 、R 3 Represented by hydrogen atom, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, or the likeA substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted piperonyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group;
The R is 4 、R 5 、R 6 Represented as one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted piperonyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted carbazolyl group;
the substituent of the substituted or substituted group is selected from one or more of deuterium atom, methyl, deuterated methyl, ethyl, tertiary butyl, adamantyl, phenyl, naphthyl and biphenyl.
6. The organic compound according to any one of claims 1 to 4, wherein the formula (2) is represented by any one of the following structures:
the formula (3) is represented by any one of the following structures:
the formula (4) is represented by any one of the following structures:
7. The organic compound according to claim 1, wherein the specific structure of the organic compound is any one of the following structures:
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8. an organic electroluminescent device comprising, in order, an anode, a hole transporting region, a light emitting region, an electron transporting region, and a cathode, wherein the hole transporting region comprises the organic compound according to any one of claims 1 to 7.
9. The organic electroluminescent device according to claim 8, wherein the hole transport region comprises a hole injection layer, a hole transport layer, and an electron blocking layer, the hole transport layer comprising the organic compound according to any one of claims 1 to 7.
10. A lighting or display element, characterized in that it comprises the organic electroluminescent device as claimed in claims 8-9.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210725307.2A CN117327005A (en) | 2022-06-24 | 2022-06-24 | Organic compound and organic electroluminescent device prepared from same |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210725307.2A CN117327005A (en) | 2022-06-24 | 2022-06-24 | Organic compound and organic electroluminescent device prepared from same |
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| CN117327005A true CN117327005A (en) | 2024-01-02 |
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| CN202210725307.2A Pending CN117327005A (en) | 2022-06-24 | 2022-06-24 | Organic compound and organic electroluminescent device prepared from same |
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