CN116789653A - Organic compound and organic electroluminescent device containing same - Google Patents
Organic compound and organic electroluminescent device containing same Download PDFInfo
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- CN116789653A CN116789653A CN202210241525.9A CN202210241525A CN116789653A CN 116789653 A CN116789653 A CN 116789653A CN 202210241525 A CN202210241525 A CN 202210241525A CN 116789653 A CN116789653 A CN 116789653A
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 25
- 239000000463 material Substances 0.000 claims abstract description 53
- 239000010410 layer Substances 0.000 claims description 71
- -1 nitro, hydroxyl Chemical group 0.000 claims description 58
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 230000005525 hole transport Effects 0.000 claims description 13
- 238000006467 substitution reaction Methods 0.000 claims description 13
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 9
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 9
- 229910052805 deuterium Inorganic materials 0.000 claims description 9
- 230000000903 blocking effect Effects 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000010409 thin film Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 3
- 230000005669 field effect Effects 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000006616 biphenylamine group Chemical group 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 125000004306 triazinyl group Chemical group 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- 239000002346 layers by function Substances 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 abstract description 121
- 239000000543 intermediate Substances 0.000 description 50
- 238000003786 synthesis reaction Methods 0.000 description 36
- 230000015572 biosynthetic process Effects 0.000 description 35
- 238000006243 chemical reaction Methods 0.000 description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 238000000034 method Methods 0.000 description 22
- 238000002360 preparation method Methods 0.000 description 17
- 238000002347 injection Methods 0.000 description 16
- 239000007924 injection Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 15
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 238000002390 rotary evaporation Methods 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 238000004440 column chromatography Methods 0.000 description 11
- 238000005516 engineering process Methods 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 9
- 239000002019 doping agent Substances 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 125000005259 triarylamine group Chemical group 0.000 description 7
- XSDKKRKTDZMKCH-UHFFFAOYSA-N 9-(4-bromophenyl)carbazole Chemical compound C1=CC(Br)=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 XSDKKRKTDZMKCH-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- 239000002356 single layer Substances 0.000 description 6
- 238000010189 synthetic method Methods 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 238000005401 electroluminescence Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- DRNWNTAANHEQMK-UHFFFAOYSA-N 1-bromo-3-chloro-2-fluorobenzene Chemical compound FC1=C(Cl)C=CC=C1Br DRNWNTAANHEQMK-UHFFFAOYSA-N 0.000 description 4
- URUDGARERYTKAD-UHFFFAOYSA-N 1-bromo-8-methoxynaphthalene Chemical compound C1=CC(Br)=C2C(OC)=CC=CC2=C1 URUDGARERYTKAD-UHFFFAOYSA-N 0.000 description 4
- UGFOTZLGPPWNPY-UHFFFAOYSA-N 7h-benzo[c]carbazole Chemical compound C1=CC=CC2=C3C4=CC=CC=C4NC3=CC=C21 UGFOTZLGPPWNPY-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 230000005012 migration Effects 0.000 description 3
- 238000013508 migration Methods 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 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 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IPWBFGUBXWMIPR-UHFFFAOYSA-N 1-bromo-2-fluorobenzene Chemical compound FC1=CC=CC=C1Br IPWBFGUBXWMIPR-UHFFFAOYSA-N 0.000 description 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 2
- DSJHYRQILJITBY-UHFFFAOYSA-N 7h-dibenzocarbazole Chemical group C12=CC=CC=C2N=C2C1=C1C=CC=CC1=C1C=CCC=C12 DSJHYRQILJITBY-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052769 Ytterbium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000005693 optoelectronics Effects 0.000 description 2
- 239000001301 oxygen 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
- 229920000642 polymer Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 238000002207 thermal evaporation Methods 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- OIRHKGBNGGSCGS-UHFFFAOYSA-N 1-bromo-2-iodobenzene Chemical compound BrC1=CC=CC=C1I OIRHKGBNGGSCGS-UHFFFAOYSA-N 0.000 description 1
- FPNVMCMDWZNTEU-UHFFFAOYSA-N 1-bromo-4-chloro-2-fluorobenzene Chemical group FC1=CC(Cl)=CC=C1Br FPNVMCMDWZNTEU-UHFFFAOYSA-N 0.000 description 1
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- YFFUYGSLQXVHMB-UHFFFAOYSA-N 2-bromo-4-chloro-1-fluorobenzene Chemical group FC1=CC=C(Cl)C=C1Br YFFUYGSLQXVHMB-UHFFFAOYSA-N 0.000 description 1
- JNGKNTZYAKKNLQ-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1h-triazine Chemical compound N=1N(Cl)NC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 JNGKNTZYAKKNLQ-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- MSAUMAWVSPLISW-UHFFFAOYSA-N 9-phenylcarbazol-3-amine Chemical group C12=CC=CC=C2C2=CC(N)=CC=C2N1C1=CC=CC=C1 MSAUMAWVSPLISW-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- 101000930898 Cryphonectria parasitica Glyceraldehyde-3-phosphate dehydrogenase Proteins 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 241000720974 Protium Species 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 101000766357 Ruditapes philippinarum Big defensin Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- JAZNSOPOXXXZQO-UHFFFAOYSA-N [N].CCO Chemical compound [N].CCO JAZNSOPOXXXZQO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 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
- LPTWEDZIPSKWDG-UHFFFAOYSA-N benzenesulfonic acid;dodecane Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCCCCCCCCCCC LPTWEDZIPSKWDG-UHFFFAOYSA-N 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000012761 high-performance material Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002503 iridium Chemical class 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 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
- 239000002861 polymer material Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 102220214919 rs1060503975 Human genes 0.000 description 1
- 102200027014 rs80356663 Human genes 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000000126 substance Substances 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
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to an organic compound, belongs to the technical field of organic luminescent materials, and simultaneously relates to application of the compound and an organic electroluminescent device comprising the compound. The organic compound of the present invention has a structure as shown in formula (1). The compound of the invention can be effectively improved when being used as a main body material of an OLED device, in particular to a red light main body materialThe lifetime of the device while ensuring good device efficiency and drive voltage.
Description
Technical Field
The invention relates to an organic compound which can be applied to an organic device, in particular to an organic compound with a triarylamine structure, wherein carbazole or derivatives thereof bridge a six-membered heteroaromatic ring containing an oxygen atom for supplying power through an aromatic ring. The invention also relates to application of the material in an organic electroluminescent device.
Background
In recent years, optoelectronic devices based on organic materials have been rapidly developed, and have become a hot spot for research in the field. Examples of such organic optoelectronic devices include Organic Light Emitting Diodes (OLEDs), organic field effect transistors, organic photovoltaic cells, organic sensors, and the like. Among them, OLED has been developed particularly rapidly, and has been commercially successful in the field of information display. OLED can provide three colors of red, green and blue with high saturation, and the full-color display device manufactured by the OLED does not need extra backlight source, and has the advantages of colorful, light, thin, soft and the like.
The OLED device core is a multi-layer thin film structure containing a plurality of organic functional materials. Common functionalized organic materials are: a hole injecting material, a hole transporting material, a hole blocking material, an electron injecting material, an electron transporting material, an electron blocking material, a light emitting host material, a light emitting guest (dye), and the like. When energized, electrons and holes are injected, transported to the light emitting region, respectively, and recombined therein, thereby generating excitons and emitting light.
Common fluorescent emitters emit light mainly using singlet excitons generated when electrons and holes are combined, and are still widely used in various OLED products. Some metal complexes, such as iridium complexes, can emit light using both triplet and singlet excitons, known as phosphorescent emitters, and can have energy conversion efficiencies up to four times greater than conventional fluorescent emitters. The thermal excitation delayed fluorescence (TADF) technique can achieve higher luminous efficiency by promoting transition from triplet excitons to singlet excitons, and still effectively utilizing triplet excitons without using a metal complex. The thermal excitation sensitized fluorescence (TASF) technology adopts a material with TADF property to sensitize the luminophor by means of energy transfer, and can also realize higher luminous efficiency.
Although products using OLED display technology are commercialized at present, performance such as lifetime and efficiency of devices is still required to be continuously improved, so as to meet pursuit of higher quality. Improving the properties of the host material is a common method in the art to increase the efficiency of the device.
Disclosure of Invention
In order to solve the technical problems, the invention provides an organic compound, which specifically adopts a triarylamine structure of carbazole or derivatives thereof, wherein the triarylamine structure contains a six-membered heteroaromatic ring of oxygen atoms for supplying power, through aromatic ring bridging, as a parent nucleus structure.
Specifically, the invention provides an organic compound, which has a structure shown as a formula (I):
in the formula (I), Y is O or S; a is a structure represented by formula (a);
L 1 and L 2 Each independently is one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group;
ar is one of a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group;
R 1 、R 2 、R 3 、R 4 each represents a substituent group of a single substitution to the maximum allowable number of substitutions, R 1 、R 2 Each connected to a benzene ring singly or in condensed form, R 1 And R is R 2 Are connected with each other to form a ring or not, different R 1 Are connected with each other to form a ring or are not connected with each other to form a ring; different R 2 Are connected with each other to form a ring or are not connected with each other to form a ring;
R 1 、R 2 、R 3 、R 4 independent of each otherIs any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;
"to" are the connection sites;
when each of the above-mentioned substituted or unsubstituted groups has a substituent group, the substituent group is selected from one or a combination of two of deuterium, halogen, cyano, nitro, hydroxyl, amino, aldehyde, ester, C1-C30 alkyl, C3-C20 cycloalkyl, C1-C30 alkoxy, C3-C20 heterocycloalkyl, C6-C60 aryloxy, C6-C60 arylamino, C6-C60 aryl, and C3-C60 heteroaryl.
In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or may be substituted with a plurality of substituents, and when the number of substituents is plural, the substituents may be selected from different substituents, and the same meaning is given when the same expression mode is involved in the present invention, and the selection ranges of the substituents are not repeated as shown above.
In the present specification, the expression of Ca to Cb means that the group has a carbon number of a to b, and unless otherwise specified, the carbon number generally excludes the carbon number of a substituent.
In the present specification, "each independently" means that the subject has a plurality of subjects, and the subjects may be the same or different from each other.
In the present invention, unless otherwise specified, the expression of a chemical element generally includes the concept of its isotope, for example, the expression of "hydrogen (H)", and includes its isotope 1 H (protium or H), 2 The concept of H (deuterium or D); carbon (C) then comprises 12 C、 13 C, etc., and are not described in detail.
The heteroatom in the heteroaryl groups in the present invention generally refers to an atom or group of atoms selected from N, O, S, P, si and Se, preferably selected from N, O, S.
In the present specification, examples of halogen include: fluorine, chlorine, bromine, iodine, and the like.
In the present invention, the substituted or unsubstituted C6-C60 aryl group, the substituted or unsubstituted C6-C30 aryl group includes both monocyclic aryl groups and condensed ring aryl groups, preferably C6-C20 aryl groups. By monocyclic aryl is meant that the molecule contains at least one phenyl group, and when the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and are linked by a single bond, such as, for example: phenyl, biphenyl, terphenyl, and the like. Specifically, the biphenyl group includes a 2-biphenyl group, a 3-biphenyl group, and a 4-biphenyl group; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl. Condensed ring aryl refers to a group in which at least two aromatic rings are contained in the molecule, and the aromatic rings are not independent of each other but share two adjacent carbon atoms condensed with each other. Exemplary are as follows: naphthyl, anthryl, phenanthryl, indenyl, fluorenyl, fluoranthryl, triphenylenyl, pyrenyl, perylenyl,And a radical, a tetracenyl radical, a derivative thereof, and the like. The naphthyl comprises 1-naphthyl or 2-naphthyl; the anthracenyl is selected from 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetracenyl is selected from the group consisting of 1-tetracenyl, 2-tetracenyl and 9-tetracenyl. The derivative group of the fluorene is selected from 9, 9-dimethylfluorenyl, 9-diethyl fluorenyl, 9-dipropyl fluorenyl, 9-dibutyl fluorenyl 9, 9-dipentylfluorenyl, 9-dihexylfluorenyl, 9-diphenylfluorenyl, 9-dinaphthylfluorenyl, 9' -spirobifluorene, and benzofluorenyl.
In the present invention, the substituted or unsubstituted C3 to C60 heteroaryl group and the substituted or unsubstituted C3 to C30 heteroaryl group each include a monocyclic heteroaryl group and a condensed ring heteroaryl group, preferably a C4 to C20 heteroaryl group, more preferably a C5 to C12 heteroaryl group. Monocyclic heteroaryl means that the molecule contains at least one heteroaryl group, and when the molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and the other groups are independent of each other and are linked by a single bond, and examples of the monocyclic heteroaryl group include: furyl, thienyl, pyrrolyl, pyridyl, and the like. Condensed ring heteroaryl means a group in which at least one aromatic heterocyclic ring and one aromatic ring (aromatic heterocyclic ring or aromatic ring) are contained in a molecule and two adjacent atoms are fused together without being independent of each other. Examples of fused ring heteroaryl groups include: benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, acridinyl, isobenzofuranyl, isobenzothiophenyl, benzocarbazolyl, azacarbazolyl, phenothiazinyl, phenazinyl, 9-phenylcarbazolyl, 9-naphthylcarbazolyl, dibenzocarbazolyl, indolocarbazolyl, and the like.
The alkyl group mentioned in the present invention includes a straight chain alkyl group and a branched chain alkyl group unless otherwise specified. Specifically, a substituted or unsubstituted C1-C30 alkyl group is preferable, and a substituted or unsubstituted C1-C16 alkyl group is more preferable. Substituted or unsubstituted C3-C30 cycloalkyl, preferably substituted or unsubstituted C3-C20 cycloalkyl, more preferably substituted or unsubstituted C3-C10 cycloalkyl, for example: methyl, ethyl, n-propyl, isopropyl, n-butyl, n-hexyl, n-octyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, tert-pentyl, cyclohexyl, adamantyl and the like.
In the present invention, the expression "ring structure" means that the linking site is located at any position on the ring structure that can be bonded.
Further preferably, the organic compound of the present invention is characterized in that in the formula (I), a is a structure represented by any one of the formulas (a 1), (a 2), (a 3), (a 4), (a 5), (a 6), (a 7), and (a 8);
R 1 、R 2 is as defined in formula (a);
R 5 、R 6 each independently is one or two of hydrogen, deuterium, C1-C30 alkyl, C3-C20 cycloalkyl, C1-C30 alkoxy, C3-C20 heterocycloalkyl, C6-C60 aryloxy, C6-C60 arylamine, C6-C60 aryl and C3-C60 heteroaryl.
Further preferably, the organic compound of the present invention has a structure represented by the following formula:
therein, Y, ar, A, R 1 、R 2 、R 3 、R 4 、L 1 And L 2 Is as defined for formula (I).
Still further, in formula (I), L 1 And L 2 Each independently is one of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group;
preferably, L 1 And L 2 Each independently is a single bond or phenylene.
Still further, in formula (I), ar is selected from one of the following substituted or unsubstituted groups: phenyl, naphthyl, anthracenyl, phenanthrenyl, biphenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirofluorenyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triazinyl, triazolyl, pyridyl, pyrimidinyl, quinazolinyl, quinoxalinyl, benzimidazolyl, benzinzazolyl, benzocarbazolyl, benzofuranocarbazolyl, benzothiocarbazolyl, indolocarbazolyl, azadibenzothiophenyl, azadibenzofuranyl, phenylamino, naphthylamino or biphenylamino;
when Ar has a substituent group, the substituent group is selected from deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C3-C10 heterocycloalkyl, C6-C60 aryl, or C3-C60 heteroaryl.
Further, the compounds of the general formula of the present invention are preferably the following specific compounds, but the present invention is not limited to the specific compounds shown below:
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it is a second object of the present invention to provide the use of a compound according to one of the objects, which is applied to an organic electroluminescent device.
Preferably, the compound is used as a light emitting layer material of the organic electroluminescent device, preferably as a light emitting layer host material of the organic electroluminescent device, further preferably as a P-type red light host material.
Or preferably, the organic compound is used as an electron blocking layer material in an organic electroluminescent device.
The compound provided by the invention can be also applied to optical sensors, solar cells, lighting elements, organic thin film transistors, organic field effect transistors, organic thin film solar cells, information labels, electronic artificial skin sheets, sheet scanners or electronic papers.
It is a further object of the present invention to provide an organic electroluminescent device comprising a first electrode, a second electrode and at least one organic layer interposed between the first electrode and the second electrode, the organic layer comprising at least one compound according to one of the objects.
Preferably, the organic layer comprises a light-emitting layer containing at least one compound of one of the purposes.
Preferably, the light-emitting layer contains the organic compound according to any one of claims 1 to 7 as a light-emitting host material, and the light-emitting layer contains an N-type host material.
The N-type host material is a conjugated compound with a lower LUMO energy level, and has better electron injection characteristic and electron transmission performance. The LUMO energy level of the compound is often < -2.2eV, and the preferred LUMO energy level is < -2.4eV. Illustratively, the N-type host material may contain one or more of pyridine, pyrimidine, pyridazine, triazine, imidazole, oxadiazole, triazole, and the like electron withdrawing groups, but is not limited thereto. .
The compound adopts a triarylamine structure with carbazole and derivatives thereof bridging six-membered heteroaromatic rings containing oxygen atoms for supplying power through aromatic rings on the whole molecular structure, thus forming a novel P-type main body material. The carbazole and its derivative have good hole migration and injection capability through the whole molecular structure of the aromatic amine of the aromatic ring bridge Lian San due to good hole migration capability and proper HOMO energy level. The compound of the invention introduces the oxygen-containing six-membered large-plane conjugated heterocycle with power supply capability into the triarylamine structure, and further enhances the hole injection and migration capability of molecules, thereby obtaining the hole injection and transport capability which is more matched with the electron transport and injection of the N-type main body material, so that the compound of the invention is applied to the organic electroluminescent device, and has excellent photoelectric property and good stability on the whole.
When the compound is used as a main material, the compound has the following beneficial effects compared with the prior art: when the compound is used as a main body material of an OLED device, particularly a red light main body material, the service life of the device can be effectively prolonged, and meanwhile, good device efficiency and driving voltage are ensured.
In one embodiment, the organic layer may further include a hole transport region and an electron transport region.
In one embodiment, a substrate may be used under the first electrode or over the second electrode. The substrates are all glass or polymer materials with excellent mechanical strength, thermal stability, water resistance and transparency. A Thin Film Transistor (TFT) may be provided on a substrate for a display.
When the compound is used as a luminescent material, particularly as a red light main body material, the compound has good luminescent performance, and is beneficial to improving the luminescent efficiency of the device.
The compound of the invention is suitable for being used as a functional material of an organic light-emitting device. However, the application of the compound of the present invention is not limited to organic light emitting devices. Such organic electronic devices include, but are not limited to, organic electroluminescent devices, optical sensors, solar cells, lighting elements, information labels, electronic artificial skin sheets, sheet scanners or electronic papers, preferably organic electroluminescent devices.
The OLED device prepared by the compound has low starting voltage, high luminous efficiency and better service life, and can meet the requirements of current panel and display manufacturing enterprises on high-performance materials.
The compound shown in the invention can be used as a main material, is suitable for OLED devices, and can effectively improve the performance of the devices. The OLED device has good carrier transmission performance and high luminous efficiency, and has potential application in solving the problem of efficiency roll-off of the OLED device under high current density and prolonging the service life of the device.
Detailed Description
The technical scheme of the invention is further more specifically described below. It should be apparent to those skilled in the art that the detailed description, as well as the examples, are merely intended to facilitate an understanding of the invention and are not intended to limit the invention to the particular forms disclosed.
The compounds of formula (I) according to the invention can be obtained by known methods, for example by known organic synthesis methods. Exemplary synthetic routes are given below, but may be obtained by other methods known to those skilled in the art. The representative synthetic route for the compounds of the general formula of the present invention is as follows:
synthesizing a general formula 1: synthesis of intermediate M1
Firstly, 1-bromo-8-methoxynaphthalene is taken as a raw material, and reacts with triisopropyl borate under the action of n-butyllithium to generate 8-methoxy-1-naphthalene boric acid M1-1; step two, intermediate M1-1 and 2-bromo-3 (or 4,5, 6) -chlorofluorobenzene are subjected to Suzuki coupling reaction to generate intermediate M1-3; step three, the intermediate M1-3 is demethylated under the action of boron tribromide to generate an intermediate M1-4; fourthly, the intermediate M1-4 is subjected to ring closure reaction under the action of cesium carbonate to generate an intermediate M1.
Synthesizing a general formula 2: synthesis of intermediate M2
The intermediate M2 is synthesized by adopting a method similar to the general formula I, except that chloro-8-methoxy-1-bromonaphthalene is used as a raw material to replace 1-bromo-8-methoxynaphthalene, 2-bromofluorobenzene is used as a starting material to replace 2-bromo-3 (or 4,5, 6) -chlorofluorobenzene.
Specific synthetic examples:
the present invention provides, by way of example, specific synthetic methods for representative compounds, such as solvents and reagents, intermediates, ethyl acetate, methanol, ethanol, and other chemical reagents used in the following synthesis examples, all of which may be purchased or customized from the domestic chemical product market.
Intermediate Synthesis example：
Synthesis of intermediate M1A
Preparation of Compound M1A-1
8-methoxy-1-bromonaphthalene (236 g), anhydrous tetrahydrofuran (2L) and liquid nitrogen ethanol are added into a dry three-neck flask under the protection of nitrogen, the temperature is reduced to minus 78 ℃, n-butyllithium (0.44L) (2.5M) is added dropwise, the temperature is kept for half an hour after the dropwise addition, triisopropylborate potassium carbonate (225 g) is added dropwise at minus 78 ℃, the dropwise addition is completed, and the temperature is naturally raised to room temperature for stirring reaction for 2 hours. Adding water to quench reaction, and separating liquid. The aqueous phase was extracted with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporation under reduced pressure, and the obtained crude product was purified by column chromatography to give Compound M1A-1 (145 g).
Preparation of Compounds M1A-2
Intermediate M1A-1 (40.4 g), 2-bromo-6-chlorofluorobenzene (41.6 g), potassium carbonate (83 g) was dissolved in a three-necked flask containing toluene/ethanol/water 0.5/0.1/0.1L, and after nitrogen substitution under stirring, tetrakis triphenylphosphine palladium (2.3 g) was added thereto, and the reaction system was heated to reflux to react for 8 hours. TLC followed the reaction. Cooling to room temperature, separating, extracting the aqueous phase with ethyl acetate, mixing the organic phases, washing with saturated saline solution, drying with anhydrous sodium sulfate, filtering, removing the solvent by rotary evaporation under reduced pressure, and purifying by column chromatography to obtain the compound M1A-2 (43 g).
Preparation of Compounds M1A-3
Intermediate M1A-2 (43 g) and 0.5L of methylene chloride were added to a three-necked flask, boron tribromide (37 g) was added dropwise with stirring, and the reaction was carried out at room temperature for 3 hours after the addition, and TLC showed that the reaction of the starting materials was completed. The reaction system was slowly poured into stirring ice water to quench. The solution was separated, the aqueous phase was extracted with methylene chloride, the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporation under reduced pressure, and the crude product was directly used for the next reaction.
Preparation of Compound M1A
The intermediate M1A-3 obtained in the above reaction was dissolved in a three-necked flask containing 400 mM, and cesium carbonate (98 g) was added. The reaction was heated to 120℃with stirring for 6 hours, and TLC followed by completion of the reaction. After cooling to room temperature, the reaction was also poured into stirred water, the precipitated solids were filtered, rinsed with water and ethanol, respectively, and dried to give compound M1A (23 g).
Synthesis of intermediate M1B
The synthesis of intermediate M1B was performed by a similar method to that of intermediate M1A, except that the starting material 2-bromo-6-chlorofluorobenzene was replaced with 2-bromo-5-chlorofluorobenzene.
Intermediate M1C synthesis
The synthesis of intermediate M1C employs a similar synthetic method to intermediate M1A, except that the starting material 2-bromo-6-chlorofluorobenzene is replaced with 2-bromo-4-chlorofluorobenzene.
Synthesis of intermediate M2A
The synthesis of intermediate M2A was performed by a similar method to intermediate M1A, except that the starting material 8-methoxy-1-bromonaphthalene was replaced with 1-bromo-7-chloro-8-methoxynaphthalene and 2-bromo-6-chlorofluorobenzene was replaced with 2-bromofluorobenzene.
Synthesis example 1: synthesis of Compound C1
Preparation of Compound C1-1
Intermediate M2A (8 g), aniline (3.5 g), sodium t-butoxide (9.3 g), tris (dibenzylidene-BASE acetone) dipalladium (0) (300 mg), 1, 3-bis (2, 6-diisopropylphenyl) 2-chloroimidazolium hydrochloride (280 mg) were dissolved in a three-necked flask containing 200mL of toluene, and the mixture was refluxed for 30 hours after nitrogen substitution. TLC followed the reaction. The reaction solution was cooled to room temperature, washed with water, separated, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporation under reduced pressure, followed by purification by column chromatography to give intermediate compound C1-1 (6.5 g).
Preparation of Compound C1
Intermediate C1-1 (6.5 g), 9- (4-bromophenyl) carbazole (7.4 g), sodium t-butoxide (6 g), tris (dibenzylidene-BASE acetone) dipalladium (0) (200 mg), 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (200 mg) were dissolved in a three-necked flask containing 150mL of toluene, and the mixture was refluxed for 20 hours after the nitrogen substitution. TLC followed the reaction. The reaction solution was cooled to room temperature, washed with water, separated, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporation under reduced pressure, followed by purification by column chromatography to give Compound C1 (7.8 g). Calculated molecular weight: 550.20, found m/z:551.1 (M+1).
Synthesis example 2：
Synthesis of Compound C16
Preparation of Compound C16-1
Intermediate M2A (10 g), pinacol biborate (15 g), potassium acetate (11.5 g), tris (dibenzylidene-BASE acetone) dipalladium (0) (366 mg), 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (330 mg) were dissolved in a three-necked flask containing 200ml of 1, 4-dioxane, and the mixture was refluxed for 8 hours after nitrogen substitution. TLC followed the reaction. The reaction solution was cooled to room temperature, the solvent was then removed by rotary evaporation under reduced pressure, DCM was dissolved, the mixture was washed with water, the organic phase was dried over anhydrous sodium sulfate, filtered, the solvent was removed by rotary evaporation under reduced pressure, and the intermediate compound C16-1 (11 g) was obtained by column chromatography purification.
Preparation of Compound C16-2
Intermediate C16-1 (11 g), p-bromoiodobenzene (10 g), potassium carbonate (13 g), and tetrakis triphenylphosphine palladium (370 mg) were dissolved in a three-necked flask containing toluene/ethanol/water 150/50/50mL, and the mixture was refluxed for 4 hours after nitrogen substitution. TLC followed the reaction. The reaction solution was cooled to room temperature, the solution was separated, the aqueous phase was extracted with toluene, the combined organic phases were dried over anhydrous sodium sulfate, filtered, the solvent was removed by rotary evaporation under reduced pressure, and the intermediate compound C16-2 (9 g) was purified by column chromatography.
Preparation of Compound C16-3
Intermediate C16-2 (9 g), aniline (2.5 g), sodium t-butoxide (7 g), tris (dibenzylidene-BASE acetone) dipalladium (0) (220 mg), 1, 3-bis (2, 6-diisopropylphenyl) 2-chloroimidazolium hydrochloride (220 mg) were dissolved in a three-necked flask containing 150mL of toluene, and the mixture was refluxed for 33 hours after nitrogen substitution. TLC followed the reaction. The reaction solution was cooled to room temperature, washed with water, separated, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporation under reduced pressure, followed by purification by column chromatography to give intermediate compound C16-3 (6.2 g).
Preparation of Compound C16
Intermediate C16-3 (6.2 g), 9- (4-bromophenyl) carbazole (5.7 g), sodium t-butoxide (4.6 g), tris (dibenzylidene-BASE acetone) dipalladium (0) (150 mg), 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (150 mg) were dissolved in a three-necked flask containing 150mL of toluene, and the mixture was refluxed for 16 hours after the nitrogen substitution. TLC followed the reaction. The reaction solution was cooled to room temperature, washed with water, separated, dried over anhydrous sodium sulfate, filtered, the solvent was removed by rotary evaporation under reduced pressure, and purified by column chromatography to give Compound C16 (7 g). Calculated molecular weight: 626.24, found m/z:627.2 (M+1).
Synthesis example 3：
Synthesis of Compound C22
Preparation of Compound C22-2
7H-benzo [ C ] carbazole (21.3 g), bromoiodobenzene (34 g), sodium tert-butoxide (29 g), cuprous iodide (23 g), and 1, 10-phenanthroline (27 g) were dissolved in a three-necked flask containing 500mL toluene, and reflux reaction was performed for 10 hours after nitrogen substitution. TLC followed the reaction. The reaction solution was cooled to room temperature, filtered through celite, the solvent was removed by rotary evaporation under reduced pressure, and the intermediate compound C22-2 (30 g) was obtained by column chromatography purification.
Compound C22 was prepared using a similar synthetic method to compound C1, except that intermediate M2A was replaced with intermediate M1A, 9- (4-bromophenyl) carbazole was replaced with intermediate C22-2, and the resulting compound C22 had a calculated molecular weight: 600.22, found m/z:601.2 (M+1).
Synthesis example 4:
synthesis of Compound C39
Preparation of compound C39A similar synthetic procedure as that of compound C16 was used, except that intermediate M2A was replaced with intermediate M1B and 9- (4-bromophenyl) carbazole was replaced with intermediate C22-2, resulting in compound C39 having a calculated molecular weight: 676.25, found m/z:677.3 (M+1).
Synthesis example 5：
Synthesis of Compound C54
Preparation of compound C54 a synthesis procedure similar to that of compound C22 was employed, except that M1A was replaced with M1C, aniline was replaced with 4-aminobiphenyl, 7H-benzo [ C ] carbazole was replaced with 7H-dibenzocarbazole, and the molecular weight of the resulting compound C54 was calculated: 726.27, found m/z:727.3 (M+1).
Synthesis example 6：
Synthesis of Compound C71
Preparation of compound C71A similar synthetic procedure as that of compound C54 was followed, except that M1C was replaced with M2A and 7H-dibenzocarbazole was replaced with 5-phenyl-5, 11-indolino [3,2-B ] carbazole, resulting in compound C71 having calculated molecular weight: 791.29, found m/z:792.3 (M+1).
Synthesis example 7：
Synthesis of Compound C83
Compound C83 was prepared using a similar synthetic method to compound C1, except that intermediate M2A was replaced with intermediate M1C, 9- (4-bromophenyl) carbazole was replaced with intermediate C71-2, and the resulting compound C83 was calculated as molecular weight: 674.24, found m/z:675.2 (M+1).
Synthesis example 8：
Synthesis of Compound C101
Preparation of compound C101A similar synthetic procedure as that of compound C1 was used, except that aniline was replaced with 3-amino-9-phenylcarbazole, 9- (4-bromophenyl) carbazole was replaced with intermediate C71-2, and the molecular weight of the resulting compound C101 was calculated: 839.29, found m/z:839.3 (M+1).
Synthesis example 9 of N-RH1
Synthesis of N-RH1 of N-type red light main body
Synthesis of Compound N-RH1-1
2-chloro-4, 6-diphenyltriazine (26.7 g), 4-chloro-1-naphthaleneboric acid (22.7 g), potassium carbonate (42 g), and tetrakis triphenylphosphine palladium (1.2 g) were dissolved in a three-necked flask containing toluene/ethanol/water 350/50/50mL, and the mixture was refluxed for 5 hours after the nitrogen gas was replaced. TLC followed the reaction. The reaction solution was cooled to room temperature, the solution was separated, the aqueous phase was extracted with toluene, the combined organic phases were dried over anhydrous sodium sulfate, filtered, the solvent was removed by rotary evaporation under reduced pressure, and the intermediate compound N-RH1-1 (33 g) was purified by column chromatography.
Synthesis of Compound N-RH1
Intermediate N-RH1-1 (30 g), 9-dimethylfluorene-4-boronic acid (21 g), potassium carbonate (32 g), tris (dibenzylidene-BASE acetone) dipalladium (0) (0.7 g) was dissolved in a three-necked flask containing 1, 4-dioxane/water 350/35mL, and the mixture was refluxed for 8 hours after the nitrogen was replaced. TLC followed the reaction. The reaction solution was cooled to room temperature and the solvent was removed by spinning. Dissolving in DCM, washing with water, separating, extracting the aqueous phase with DCM, drying the combined organic phases with anhydrous sodium sulfate, filtering, removing the solvent by rotary evaporation under reduced pressure, and purifying by column chromatography to obtain the intermediate compound N-RH1 (31 g). Calculated molecular weight: 551.24, found m/z:552.2 (M+1).
The specific synthetic methods of the above compounds are given in an exemplary manner, and the compounds not given in the synthetic examples are prepared by similar methods, and can be obtained by replacing raw materials, which are not described herein, or can be prepared by other methods in the prior art by a person skilled in the art.
Synthesis of D4 of Compound of comparative example 4
Compound D4 was prepared using a similar synthetic method to compound C1, except that intermediate M2A was replaced with 3-chloro-9, 9-dimethyl-7H-benzanthracene, resulting in compound D4 having a calculated molecular weight: 576.26, found m/z:577.3 (M+1).
Comparative example 5 Synthesis of Compound D5
Compound D5 was prepared using a similar synthetic procedure to compound C1, except that intermediate M2A was replaced with 3-chloro-7-phenyl-7H-benzo [ kl ] acridine (see CN106632252A for starting synthesis), resulting compound D5 molecular weight calculations: 625.25, found m/z:626.3 (M+1).
The implementation method of the organic electroluminescent device comprises the following steps:
the OLED includes a first electrode and a second electrode, and an organic material layer between the electrodes. The organic material may in turn be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
In a specific embodiment, the first electrode may be formed by sputtering or depositing a material serving as the first electrode on the substrate. When the first electrode is used as the anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO 2), zinc oxide (ZnO), or the like, and any combination thereof may be used. When the first electrode is used as the cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combinations thereof may be used.
The organic layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compounds used as the organic layer may be small organic molecules, large organic molecules and polymers, and combinations thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer hole transport layer containing only one compound and a single layer hole transport layer containing a plurality of compounds. The hole transport region may have a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL).
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or conductive dopant containing polymers such as polystyrene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives including compounds as shown below HT-1 to HT-50; or any combination thereof.
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The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more of the compounds HT-1 through HT-50 described above, or one or more of the compounds HI-1 through HI-3 described below; one or more compounds of HT-1 through HT-50 may also be used to dope one or more of HI-1 through HI-3 described below.
The luminescent layer comprises luminescent dyes (i.e. dopants) that can emit different wavelength spectra, and may also comprise Host materials (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The plurality of monochromatic light emitting layers with different colors can be arranged in a plane according to the pixel pattern, or can be stacked together to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light emitting layer may be a single color light emitting layer capable of simultaneously emitting different colors such as red, green, and blue.
According to different technologies, the luminescent layer material can be made of different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescence luminescent material and the like. In an OLED device, a single light emitting technology may be used, or a combination of different light emitting technologies may be used. The different luminescent materials classified by the technology can emit light of the same color, and can also emit light of different colors.
In one aspect of the invention, the light-emitting layer employs fluorescence electroluminescence technology. The luminescent layer fluorescent host material thereof may be selected from, but is not limited to, one or more combinations of BFH-1 to BFH-17 listed below.
In one aspect of the invention, the light-emitting layer employs fluorescence electroluminescence technology. The luminescent layer fluorescent dopant thereof may be selected from, but is not limited to, one or more combinations of BFD-1 through BFD-24 listed below.
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In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer phosphorescent dopant thereof may be selected from, but is not limited to, one or more combinations of the RPD-1 through RPD-28 listed below.
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In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer phosphorescent dopant thereof may be selected from, but is not limited to, one or more combinations of GPD-1 to GPD-47 listed below.
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In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer phosphorescent dopant may be selected from, but is not limited to, one or more combinations of YPD-1-YPD-11 listed below.
The electron transport region may be an Electron Transport Layer (ETL) of a single layer structure including a single layer electron transport layer containing only one compound and a single layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
In one aspect of the invention, the electron transport layer material may be selected from, but is not limited to, combinations of one or more of ET-1 through ET-73 listed below.
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An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, a combination of one or more of the following.
Liq、LiF、NaCl、CsF、Li 2 O、Cs 2 CO 3 、BaO、Na、Li、Ca、Yb。
The cathode is magnesium-silver mixture, liF/Al, ITO and other metals, metal mixtures and oxides.
Device example:
device example 1:
the embodiment provides an organic electroluminescent device, which is prepared by the following steps:
the glass plate coated with the ITO transparent conductive layer was sonicated in commercial cleaners, rinsed in deionized water, and rinsed in acetone: ultrasonic degreasing in ethanol mixed solvent, baking in clean environment to completely remove water, cleaning with ultraviolet light and ozone, and bombarding surface with low-energy cation beam;
placing the glass substrate with ITO anode into a vacuum chamber, and vacuumizing to 10 -5 Pa, vacuum thermal evaporation of 10nm HT-4/HI-3 (97/3,w/w) mixture as hole injection layer on the anode layer film; a 60nm compound HT-4 as a hole transport layer; 60nm compound HT-47 as an electron blocking layer material for the device; a 40nm light emitting layer; 5nm ET-17 as hole blocking layer of the device; a 25nm compound ET-69:ET-57 (50/50, w/w) mixture as an electron transport layer; 1nm LiF as an electron injection layer; 150nm of metallic aluminum was used as the cathode. The light-emitting layer is formed by using a compound C1 and a compound N-RH1 of the invention as a first host compound and a second host compound respectively, and a compound RPD-8 as a light-emitting dopant; wherein the ratio of C1 to N-RH1 is 1:1, RPD-8 accounts for 3% of the total amount of the luminescent layer, the total vapor deposition rate of all organic layers and LiF is controlled at 0.1 nm/sec, and the vapor deposition rate of the metal electrode is controlled at 1 nm/sec.
Device examples 2-8:
device examples 2-8 were prepared following the preparation procedure of device example 1, except that the first host material in the light-emitting layer of the device prepared was replaced by C1 for the other representative compounds C16, C22, C39, C54, C71, C83, C101 of the present invention.
Comparative device examples 1-5:
comparative device examples 1-5 were prepared following the preparation procedure of device example 1, except that the first host material in the light-emitting layer of the device prepared was replaced by a prior art compound D1, D2, D3, D4, D5 by a compound C1 of the present invention.
Based on the methods reported in patent documents US20160149141A1, CN106660966A, CN11848417a, respectively, the following compounds D1, D2, D3 in the prior art were synthesized, and specific processes are not described again. The structural formula of the compound is as follows:
the following performance tests were conducted on the organic electroluminescent devices prepared in examples 1 to 8 and comparative examples 1 to 5, and the test results are shown in table 1 below.
The voltage and efficiency of the device were at a luminance of 3000cd/m 2 And (3) measuring the following. The device lifetime (LT 97) was tested as follows: maintaining at 60mA/cm 2 The constant current, the time in hours for the luminance of the organic electroluminescent device to drop to 97% of the initial luminance, was measured. The lifetime of the other devices was a relative value to that of comparative example 1, with the lifetime of comparative example 1 being 100.
Table 1:
as can be seen from table 1, the compounds provided by the present invention can obtain lower driving voltage, higher current efficiency and longer device lifetime when used as host materials of organic electroluminescent devices. This is presumably due to the fact that the triarylamine structure provided by the invention, in which carbazole or its derivative is bridged through an aromatic ring to have a six-membered heteroaromatic ring containing a donor oxygen atom, has a stronger electron donating ability and a larger conjugated plane, and also has a suitable HOMO level, thereby being capable of providing a stronger hole injecting and transporting ability, and having an electron injecting and transporting ability more matching with that of the N-type host material.
Specifically, the compounds of the present invention have a significant difference in hole injection and transport ability from the compounds of the present invention because the 3 comparative examples have a molecular structure which is greatly different from the molecule of the present invention as a whole, and no carbazole (or derivative thereof) is formed through the aromatic ring bridge Lian San aromatic amine structure, as compared with the compounds D1 to D3 of comparative examples 1 to 3. Compared with the compounds D4-D5 in comparative examples 4-5, the compound of the invention has relatively stronger hole injection and transmission capacity due to the fact that the compound of the invention introduces the oxygen-containing six-membered heterocycle with stronger planeness and power supply capacity into the triarylamine part, and better device effect is obtained when the compound of the invention is applied to a device structure.
The experimental data show that the organic material provided by the invention is used as a red light main body material of an organic electroluminescent device, has good performance and has a wide application prospect.
The present invention is described in detail by the above examples, but the present invention is not limited to the above detailed methods, i.e., it does not mean that the present invention must be practiced depending on the above detailed methods. While the invention has been described in connection with the embodiments, it is to be understood that the invention is not limited to the above embodiments, but is capable of numerous modifications and improvements by those skilled in the art under the guidance of the inventive concept, and the scope of the invention is outlined in the appended claims, and equivalent substitutions for various raw materials of the inventive product, addition of auxiliary components, selection of specific modes, etc., are all within the scope of the invention and the scope of the disclosure.
Claims (9)
1. An organic compound having a structure represented by the formula (I):
in the formula (I), Y is O or S; a is a structure represented by formula (a);
L 1 and L 2 Each independently is one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group;
ar is one of a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group;
R 1 、R 2 、R 3 、R 4 each represents a substituent group of a single substitution to the maximum allowable number of substitutions, R 1 、R 2 Each connected to a benzene ring singly or in condensed form, R 1 And R is R 2 Are connected with each other to form a ring or not, different R 1 Are connected with each other to form a ring or not, different R 2 Are connected with each other to form a ring or are not connected with each other to form a ring;
R 1 、R 2 、R 3 、R 4 each independently is any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;
"to" are the connection sites;
when each of the above-mentioned substituted or unsubstituted groups has a substituent group, the substituent group is selected from one or a combination of two of deuterium, halogen, cyano, nitro, hydroxyl, amino, aldehyde, ester, C1-C30 alkyl, C3-C20 cycloalkyl, C1-C30 alkoxy, C3-C20 heterocycloalkyl, C6-C60 aryloxy, C6-C60 arylamino, C6-C60 aryl, and C3-C60 heteroaryl.
2. The organic compound according to claim 1, wherein in the formula (I), a is a structure represented by any one of formulas (a 1), (a 2), (a 3), (a 4), (a 5), (a 6), (a 7), and (a 8);
R 1 、R 2 is as defined in formula (a);
R 5 、R 6 each independently is one or two of hydrogen, deuterium, C1-C30 alkyl, C3-C20 cycloalkyl, C1-C30 alkoxy, C3-C20 heterocycloalkyl, C6-C60 aryloxy, C6-C60 arylamine, C6-C60 aryl and C3-C60 heteroaryl.
3. The organic compound according to claim 1 or 2, characterized by having a structure represented by the following formula:
therein, Y, ar, A, R 1 、R 2 、R 3 、R 4 、L 1 And L 2 Is as defined for formula (I).
4. An organic compound according to any one of claims 1 to 3, wherein L 1 And L 2 Each independently is one of a single bond, a substituted or unsubstituted phenylene group, and a substituted or unsubstituted naphthylene group.
5. An organic compound according to any one of claims 1 to 3, wherein L 1 And L 2 Each independently is a single bond or phenylene.
6. An organic compound according to any one of claims 1 to 3, wherein Ar is selected from one of the following substituted or unsubstituted groups: phenyl, naphthyl, anthracenyl, phenanthrenyl, biphenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirofluorenyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triazinyl, triazolyl, pyridyl, pyrimidinyl, quinazolinyl, quinoxalinyl, benzimidazolyl, benzinzazolyl, benzocarbazolyl, benzofuranocarbazolyl, benzothiocarbazolyl, indolocarbazolyl, azadibenzothiophenyl, azadibenzofuranyl, phenylamino, naphthylamino or biphenylamino;
when Ar has a substituent group, the substituent group is selected from deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C3-C10 heterocycloalkyl, C6-C60 aryl, or C3-C60 heteroaryl.
7. The organic compound according to claim 1, having a structural formula as shown below:
8. use of an organic compound according to claim 1 as a functional material in an organic electronic device selected from the group consisting of an organic electroluminescent device, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information tag, an electronic artificial skin sheet, a sheet scanner or electronic paper;
preferably, the organic compound is used as a host material for a light emitting layer in an organic electroluminescent device;
preferably, the application of the organic compound is as an electron blocking layer material in an organic electroluminescent device.
9. An organic electroluminescent device comprising a first electrode, a second electrode, and one or more light-emitting functional layers interposed between the first electrode and the second electrode, wherein the light-emitting functional layers contain the organic compound according to any one of claims 1 to 7;
preferably, the light-emitting functional layer comprises a hole transport layer, a light-emitting layer and an electron transport layer, and the light-emitting layer contains the organic compound according to any one of claims 1 to 7;
still preferably, the light-emitting layer contains the organic compound according to any one of claims 1 to 7 as a light-emitting host material, and the light-emitting layer contains an N-type host material.
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