CN117024426A - Carbazole derivative and application thereof - Google Patents
Carbazole derivative and application thereof Download PDFInfo
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- CN117024426A CN117024426A CN202310992946.XA CN202310992946A CN117024426A CN 117024426 A CN117024426 A CN 117024426A CN 202310992946 A CN202310992946 A CN 202310992946A CN 117024426 A CN117024426 A CN 117024426A
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- substituted
- unsubstituted
- group
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- carbazole derivative
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- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title claims abstract description 26
- 239000000463 material Substances 0.000 claims abstract description 40
- 239000010410 layer Substances 0.000 claims description 156
- -1 spirobifluorenyl Chemical group 0.000 claims description 59
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 238000002347 injection Methods 0.000 claims description 26
- 239000007924 injection Substances 0.000 claims description 26
- 230000000903 blocking effect Effects 0.000 claims description 20
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 230000005525 hole transport Effects 0.000 claims description 14
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 12
- 229910052805 deuterium Inorganic materials 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000005264 aryl amine group Chemical group 0.000 claims description 9
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 239000012044 organic layer Substances 0.000 claims description 9
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- 239000004305 biphenyl Substances 0.000 claims description 8
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 8
- 125000005561 phenanthryl group Chemical group 0.000 claims description 8
- 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 7
- 125000005580 triphenylene group Chemical group 0.000 claims description 7
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 5
- 125000001725 pyrenyl group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004623 carbolinyl group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
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- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000000969 carrier Substances 0.000 abstract description 2
- 230000002035 prolonged effect Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 38
- 239000011799 hole material Substances 0.000 description 23
- 150000001716 carbazoles Chemical class 0.000 description 20
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- 238000000034 method Methods 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 239000007787 solid Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
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- 238000012360 testing method Methods 0.000 description 6
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- 101100348848 Mus musculus Notch4 gene Proteins 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 101100446506 Mus musculus Fgf3 gene Proteins 0.000 description 3
- 101100317378 Mus musculus Wnt3 gene Proteins 0.000 description 3
- 101000767160 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) Intracellular protein transport protein USO1 Proteins 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 3
- 125000002971 oxazolyl group Chemical group 0.000 description 3
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- 238000005092 sublimation method Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
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- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 1
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- 239000000839 emulsion Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
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- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
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- 239000011630 iodine Substances 0.000 description 1
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- 125000005990 isobenzothienyl group Chemical group 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
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- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
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- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
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- UNJZLNFHHINVOB-UHFFFAOYSA-N n-naphthalen-1-ylnaphthalen-2-amine Chemical group C1=CC=C2C(NC=3C=C4C=CC=CC4=CC=3)=CC=CC2=C1 UNJZLNFHHINVOB-UHFFFAOYSA-N 0.000 description 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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- VXNSQGRKHCZUSU-UHFFFAOYSA-N octylbenzene Chemical compound [CH2]CCCCCCCC1=CC=CC=C1 VXNSQGRKHCZUSU-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
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- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
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- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
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- 239000010452 phosphate Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000004585 polycyclic heterocycle group Chemical group 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
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- 125000006413 ring segment Chemical group 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical group [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 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
- KTQYWNARBMKMCX-UHFFFAOYSA-N tetraphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 KTQYWNARBMKMCX-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- BZHGXQBPJUHVFW-UHFFFAOYSA-N toluene;tritert-butylphosphane Chemical compound CC1=CC=CC=C1.CC(C)(C)P(C(C)(C)C)C(C)(C)C BZHGXQBPJUHVFW-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/18—Carrier blocking layers
- H10K50/181—Electron blocking layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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- 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
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Abstract
The invention relates to the technical field of organic electroluminescent materials, in particular to a carbazole derivative and application thereof. The structural formula of the carbazole derivative is shown as a formula (I); the carbazole derivative shown in the formula (I) provided by the invention has stable triplet energy level, and improves the thermal stability of the material and the capability of transporting carriers; the carbazole derivative is applied to an organic electroluminescent element, so that the driving voltage can be obviously reduced, the luminous efficiency can be improved, and the service life can be prolonged;
Description
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to a carbazole derivative and application thereof.
Background
In general, an organic light emitting phenomenon refers to a phenomenon that emits light when electric energy is applied to an organic substance; that is, when an organic layer is disposed between an anode and a cathode, if a voltage is applied between the two electrodes, holes are injected from the anode to the organic layer, and electrons are injected from the cathode to the organic layer; when the injected holes and electrons meet, excitons are formed, and when the excitons transition to a ground state, light and heat are emitted.
In recent years, organic electroluminescent display technology has tended to mature, and some products have entered the market, but in the industrialization process, many problems still remain to be solved. In particular, various organic materials for manufacturing elements, which have carrier injection and transport properties, material electroluminescent properties, service life, color purity, matching between various materials and between various electrodes, and the like, have not been solved; in particular, the luminous efficiency and the service life of the light-emitting element do not meet the practical requirements, which greatly limits the development of OLED technology. While the metal complex phosphorescent material using triplet light emission has high light emission efficiency, green and red light materials thereof have reached the use requirements, the metal complex phosphorescent material requires a phosphorescent material or a hole material having a high triplet energy level to match with, and thus, development of a phosphorescent material or a hole material having a high triplet energy level is an urgent need for the current development of OLEDs.
Under current technological development, improvements are still needed, both for fluorescent materials and for phosphorescent materials, in particular in terms of operating voltage, efficiency and lifetime for use in organic electroluminescent elements and in terms of thermal stability during sublimation.
In order to overcome the above-described problems, there is a continuing need for the development of a more stable and effective substance that can be used as a phosphorescent material or a hole material in an organic electroluminescent element, in order to further improve the characteristics of the organic electroluminescent element.
In view of this, the present invention has been made.
Disclosure of Invention
The invention aims to provide a carbazole derivative, which effectively improves the thermal stability of materials and the capability of transporting carriers, and an organic electroluminescent element prepared by using the carbazole derivative can obviously reduce driving voltage, improve luminous efficiency and prolong service life; another object of the present invention is to provide the use of the carbazole derivative.
Specifically, the invention provides the following technical scheme:
the invention provides a carbazole derivative, which has a structural formula shown in a formula (I):
wherein,
R 1 selected from hydrogen, deuterium, substituted or unsubstituted C 1 -C 40 Alkyl, substituted or unsubstituted C 3 -C 40 Cycloalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamine group, substituted or unsubstituted C 2 -C 60 A group consisting of heteroaryl groups;
R 2 、R 3 、R 4 、R 5 each independently selected from the group consisting of hydrogen, deuterium, cyano, substituted or unsubstituted C 1 -C 40 Alkyl, substituted or unsubstituted C 3 -C 40 Cycloalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamine group, substituted or unsubstituted C 2 -C 60 A heterocyclic aryl group or a group represented by formula (II); adjacent two or more R 2 、R 3 、R 4 、R 5 Optionally joined or fused to form a substituted or unsubstituted ring;
the structural formula of formula (II) is as follows:
Ar 1 、Ar 2 each independently selected from the group consisting of substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamine groups, or substituted or unsubstituted C 2 -C 60 A group consisting of heteroaryl groups; ar (Ar) 1 And Ar is a group 2 Optionally joined or fused to form a substituted or unsubstituted ring;
m is selected from integers of 0 to 5;
L 1 selected from single bonds, substituted or unsubstituted C 6 -C 60 Arylene of (2), or substituted or unsubstituted C 2 -C 60 Heteroarylene;
and- (II) represents a bond between formula (II) and formula (I).
In the present invention, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, "ring" means a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.
Preferably, the carbazole derivative is selected from the group consisting of the structures shown below:
wherein R is 1 ～R 5 、L 1 、Ar 1 、Ar 2 And m has the same meaning as defined above.
"aryl" according to the present invention refers to and includes monocyclic aromatic hydrocarbon groups and polycyclic aromatic ring systems. The polycyclic ring may have two or more rings in common in which two carbons are two adjoining rings (the rings being "fused"), wherein at least one of the rings is an aromatic hydrocarbon group, e.g., the other rings may be cycloalkyl, cycloalkenyl, aryl, heterocyclic, and/or heteroaryl. Preferred aryl groups are those containing from 6 to 30 carbon atoms, preferably from 6 to 20 carbon atoms, more preferably from 6 to 12 carbon atoms. Particularly preferred are aryl groups having six carbons, ten carbons or twelve carbons. Suitable aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthyl, anthracenyl, phenalenyl, phenanthrenyl, fluorenyl, pyrenyl, perylenyl,Radicals and azulene radicals, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorenyl and naphthyl. In addition, aryl groups may be optionally substituted.
"heteroaryl" or "heteroaryl" in the sense of the present invention refers to monocyclic aromatic groups and polycyclic aromatic ring systems comprising at least one heteroatom. Heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, phosphorus, boron, silicon, or selenium. In many cases oxygen, sulfur or nitrogen are preferred heteroatoms. The monocyclic heteroaromatic system is preferably a monocyclic ring having 5 or 6 ring atoms, and the ring may have one to six heteroatoms. The heteropolycyclic ring system may have two or more rings in which two atoms are common to two adjoining rings (the rings being "fused"), wherein at least one of the rings is heteroaryl, e.g., the other rings may be cycloalkyl, cycloalkenyl, aryl, heterocyclic, and/or heteroaryl. The heteropolycyclic aromatic ring system may have one to six heteroatoms in each ring of the polycyclic aromatic ring system. Preferred heteroaryl groups are those containing from three to thirty carbon atoms, preferably from three to twenty carbon atoms, more preferably from three to twelve carbon atoms. Suitable heteroaryl groups include dibenzothienyl, dibenzofuranyl, dibenzoselenophenyl, furyl, thienyl, benzofuranyl, benzothienyl, benzoselenophenyl, carbazolyl, indolocarbazolyl, pyridylindolyl, pyrrolodipyridyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, oxadiazolyl, oxazolyl, dioxazolyl, thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, oxazinyl, oxathiazinyl, oxadiazolyl, indolyl, benzimidazolyl, indazolyl, oxazinyl, and the like benzoxazolyl, benzisoxazolyl, benzothiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, phthalazinyl, pteridinyl, oxaanthracenyl (xanthene), acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, benzofuropyridinyl, furodipyridinyl, benzothiophenopyridinyl, thienodipyridinyl, benzoselenophenopyridinyl, selenophenodipyridinyl, 1, 2-azaboryl, 1, 3-azaboryl, 1, 4-azaboryl, borazine and their aza analogues, dibenzothienyl, dibenzofuranyl, dibenzoselenophenyl, carbazolyl, indolocarbazolyl, imidazolyl, pyridinyl, triazinyl, benzimidazolyl, 1, 2-azaboryl, 1, 3-azaboryl, 1, 4-azaboryl, borazaynyl and the aza analogues thereof are preferred. In addition, heteroaryl groups may be optionally substituted.
The condensed aryl or condensed ring aryl used in the present invention means a monovalent functional group obtained by removing one hydrogen atom from an aromatic hydrocarbon having 6 to 60 carbon atoms, which is a combination of two or more rings. In this case, two or more rings may be attached to each other singly or in a condensed form. As non-limiting examples thereof, there may be mentioned phenanthryl, anthracyl, fluoranthracyl, pyrenyl, triphenylenyl, perylenyl,A base, etc.
As the arylamine group used in the present invention, an arylamine group refers to an amine substituted with an aryl group having 6 to 60 carbon atoms, and as non-limiting examples of the arylamine group, there are a diphenylamino group, an N-phenyl-1-naphthylamine group, an N- (1-naphthyl) -2-naphthylamine group and the like. The heteroarylamino group means an amine substituted with an aryl group having 6 to 60 carbon atoms and a heteroaryl group having 2 to 60 carbon atoms, and as non-limiting examples of the heteroarylamino group, there are N-phenylpyridine-3-amino, N- ([ 1,1 '-biphenyl ] -4-yl) dibenzo [ b, d ] furan-2-amino, N- ([ 1,1' -biphenyl ] -4-yl) -9, 9-dimethyl-9H-fluorene-2-amino, and the like.
Preferably, the aryl, heteroaryl or heteroaryl group refers in particular to a group derived from: phenyl, naphthyl, anthryl, benzanthraceyl, phenanthryl, pyrenyl,A group, perylene group, fluoranthenyl group, naphthacene group, pentacene group, benzopyrene group, biphenyl group, terphenyl group, trimeric phenyl group, tetrabiphenyl group, fluorenyl group, spirobifluorenyl group, dihydrophenanthrene group, triphenylene group, dihydropyrenyl group, tetrahydropyrenyl group, cis-or trans-indenofluorenyl group, cis-or trans-indenocarbazolyl group, cis-or trans-indolocarbazolyl group, trimeric indenyl group, heterotrimeric indenyl group, spiro-iso-tril indenyl group, furyl group, benzofuryl group, isobenzofuryl group, dibenzofuryl group, dibenzothienyl group, isobenzothienyl group, dibenzothienyl group, pyrrolyl group, indolyl group, isoindolyl group, carbazolyl group, pyridyl group, quinolyl group, isoquinolyl group, acridinyl group, phenanthridinyl group, benzo [5,6]Quinolinyl, benzo [6,7]Quinolinyl, benzo [7,8]Quinolinyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, napthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthazolyl, anthracoxaoxazolyl, phenanthrooxazolyl, isoxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, hexaazabenzophenanthryl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthracenyl, 2, 7-diazapyrenyl, 2, 3-diazapyrenyl, 1, 6-diazapyrenyl, 1, 8-diazapyrenyl, 4,5,9, 10-tetraazaperylenyl, pyrazinyl, phenazinyl, phenothiazinyl, erythrozinyl, naphthyridinyl, 1,2, 3-triazolyl, 1, 2-triazolyl, 1, 3-naphthyridinyl,Benzotriazole group, 1,2, 3-oxadiazolyl group, 1,2, 4-oxadiazolyl group, 1,2, 5-oxadiazolyl group, 1,3, 4-oxadiazolyl group, 1,2, 3-thiadiazolyl group, 1,2, 4-thiadiazolyl group, 1,2, 5-thiadiazolyl group, 1,3, 4-thiadiazolyl group, 1,3, 5-triazinyl group, 1,2, 4-triazinyl group, 1,2, 3-triazinyl group, tetrazolyl group, 1,2,4, 5-tetrazinyl group, 1,2,3, 4-tetrazinyl group, 1,2,3, 5-tetrazinyl group, purinyl group, pteridinyl group, indolizinyl group, quinazolinyl group, benzothiadiazolyl group, or groups derived from combinations of these systems.
Preferably, the Ar 1 、Ar 2 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylene, substituted or unsubstituted triphenylene, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted indolyl, or substituted or unsubstituted carbolinyl.
Preferably, said R 1 Selected from the group consisting of hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, and furanyl, dibenzofuranyl, benzothienyl, dibenzothiophenyl, naphthyl, phenanthryl, anthracenyl, fluorenyl, spirobifluorenyl, or carbazolyl.
Preferably, said R 2 、R 3 、R 4 、R 5 Each independently selected from the group consisting of hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranylUnsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted carboline group.
Further, the R 2 、R 3 、R 4 、R 5 Each independently selected from hydrogen, deuterium, or a group of formula (II).
Preferably, the L 1 Selected from a single bond or a group consisting of groups III-1 to III-23:
wherein the dotted line represents the attachment site of the group.
Preferably, m is selected from 0, 1 or 2.
As used herein, "combination" or "group" means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that one of ordinary skill in the art can contemplate from the applicable list. For example, alkyl and deuterium can combine to form a partially or fully deuterated alkyl group; halogen and alkyl groups may combine to form haloalkyl substituents such as trifluoromethyl and the like; and halogen, alkyl and aryl may combine to form a haloaralkyl.
In one example, the term substitution includes a combination of two to four of the listed groups.
"halogen", "halogen atom", "halo" in the sense of the present invention are used interchangeably and refer to fluorine, chlorine, bromine or iodine.
In the present invention, the term "substituted or unsubstituted" means that the compound is selected from hydrogen, deuterium, halogen atom, hydroxyl group, nitrile group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxyl group or carboxylate thereof, sulfonic acid group or sulfonate thereof, phosphoric acid group or phosphate thereof, and C 1 -C 60 Alkyl, C of (2) 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Cycloalkyl, C 3 -C 60 Cycloalkenyl group of (C),C 6 -C 60 Aryl, C of (2) 6 -C 60 Aryloxy group, C 6 -C 60 Aryl sulfide group and C 2 -C 60 More than 1 substituent in the heterocyclic aryl group, or a substituent which is linked by more than 2 substituents in the above exemplified substituents.
Preferably, the carbazole derivative has a structural formula selected from the group consisting of C600 to C812:
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wherein each x— is independently selected from one of the following structures:
* -and- (x) represents a bond.
The invention also provides an organic electroluminescent material, which comprises the carbazole derivative; the organic electroluminescent material comprising the carbazole derivative of the present invention has a carrier transporting ability or a light extracting ability.
Preferably, the organic electroluminescent material is a hole injection layer material, a hole transport layer material, a hole blocking layer material, a light emitting layer material, an electron transport layer material, an electron injection layer material, a capping layer (abbreviated as CPL) or a light refracting layer material or an electron blocking layer material.
The invention also provides application of the carbazole derivative in preparation of the organic electroluminescent element.
The present invention also provides an organic electroluminescent element comprising: a first electrode, a second electrode, a CPL, and more than one organic layer disposed between the first electrode and the second electrode; at least one of the organic layer and the CPL comprises the carbazole derivative.
The organic electroluminescent element comprises a cathode, an anode, CPL and at least one light emitting layer. In addition to these layers, it may also comprise further layers, for example in each case one or more hole-injection layers, hole-transport layers, hole-blocking layers, electron-transport layers, electron-injection layers, exciton-blocking layers, electron-blocking layers and/or charge-generating layers. An intermediate layer having, for example, an exciton blocking function can likewise be introduced between the two light-emitting layers. It should be noted, however, that not every one of these layers need be present. The organic electroluminescent element described herein may include one light emitting layer, or it may include a plurality of light emitting layers. That is, a plurality of light-emitting compounds capable of emitting light are used in the light-emitting layer. Particularly preferred is a system with three light-emitting layers, wherein the three layers can display blue, green and red light emission. If more than one light-emitting layer is present, at least one of these layers comprises a compound of the invention according to the invention.
Further, the organic electroluminescent element according to the present invention does not comprise a separate hole injection layer and/or hole transport layer and/or hole blocking layer and/or electron transport layer, i.e. the light emitting layer is directly adjacent to the hole injection layer or anode and/or the light emitting layer is directly adjacent to the electron transport layer or electron injection layer or cathode.
In the other layers of the organic electroluminescent element according to the invention, in particular in the hole-transport layer and in the light-emitting layer and in the CPL, all materials can be used in the manner customary in accordance with the prior art. The person skilled in the art will thus be able to use all materials known for organic electroluminescent elements in combination with the luminescent layer according to the invention without inventive effort.
Furthermore, preference is given to organic electroluminescent elements in which one or more layers can be applied by means of a sublimation process, wherein the sublimation process is carried out in a vacuum at a temperature of less than 10 -5 Pa, preferably below 10 -6 The material is applied by vapor deposition at an initial pressure of Pa. However, the initial pressure may also be even lower, for example below 10 -7 Pa。
Also preferred are organic electroluminescent elements in which one or more layers can also be applied by means of an organic vapor deposition process or by means of carrier gas sublimation, where at 10 -5 The material is applied at a pressure between Pa and 1 Pa. A particular example of this method is an organic vapor jet printing method, wherein the material is applied directly through a nozzle and is thus structured.
Furthermore, organic electroluminescent elements are preferred, from which one or more layers are produced, for example by spin coating, or by means of any desired printing method, for example screen printing, flexography, lithography, photoinitiated thermal imaging, thermal transfer, inkjet printing or nozzle printing. Soluble compounds the soluble compounds are obtained, for example, by suitable substitution of the compounds of formula (I). These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, a hybrid method is possible, in which one or more layers are applied, for example from a solution, and one or more further layers are applied by vapor deposition.
These methods are generally known to those of ordinary skill in the art and they can be applied to the organic electroluminescent element comprising the compound according to the present invention without inventive effort.
The invention therefore also relates to a method of manufacturing an organic electroluminescent element according to the invention, comprising applying at least one layer by means of a sublimation method, and/or applying at least one layer by means of an organic vapour deposition method or by means of carrier gas sublimation, and/or applying at least one layer from solution by spin coating or by means of a printing method.
Furthermore, the present invention relates to a pharmaceutical composition comprising at least one compound of the invention as indicated above. The same preferable cases as indicated above with respect to the organic electroluminescent element apply to the compound of the present invention. In particular, the compounds may furthermore preferably comprise further compounds. Treatment of the compounds of the invention from the liquid phase, for example by spin coating or by printing methods, requires treatment of preparations of the compounds of the invention, which preparations may be, for example, solutions, dispersions or emulsions. For this purpose, it may be preferable to use a mixture of two or more solvents. Suitable and preferred solvents are, for example, toluene, anisole, o-xylene, m-xylene or p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, tetrahydrofuran, methyltetrahydrofuran, tetrahydropyran, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-) -fenchyl ketone, 1,2,3, 5-tetramethylbenzene, 1,2,4, 5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3, 4-dimethylanisole, 3, 5-dimethylanisole, acetophenone, alpha-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decahydronaphthalene, dodecylbenzene, ethyl benzoate, indane, methyl benzoate, 1-methylpyrrolidone, p-cymene, phenetole, 1, 4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1-bis (3, 4-dimethylphenyl) ethane, or mixtures of these solvents.
Preferably, the organic layer includes a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, or an electron blocking layer.
Preferably, the light-emitting layer, hole-transporting layer or electron blocking layer contains the carbazole derivative of the present invention.
In addition, unless otherwise specified, all raw materials used in the present invention are commercially available, and any ranges recited in the present invention include any numerical value between the end values and any sub-range constituted by any numerical value between the end values or any numerical value between the end values.
The beneficial effects obtained by the invention are as follows:
the carbazole derivative shown in the formula (I) provided by the invention has high triplet energy level, low refractive index, high material thermal stability and carrier conveying capacity; the carbazole derivative is applied to an organic electroluminescent element, and can remarkably reduce driving voltage, improve luminous efficiency and prolong service life.
Drawings
Fig. 1 shows a schematic diagram of an organic light emitting device 100. The illustrations are not necessarily drawn to scale. The device 100 may include a substrate 101, an anode layer 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light emitting layer 106, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, a cathode layer 110, and a capping layer (CPL) 111. The device 100 may be fabricated by sequentially depositing the layers described.
Fig. 2 shows a schematic diagram of an organic light emitting device 200 with two light emitting layers. The device includes a substrate 201, an anode layer 202, a hole injection layer 203, a hole transport layer 204, a first emissive layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second emissive layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode layer 213. The device 200 may be prepared by sequentially depositing the layers described. Because the most common OLED device has one light emitting layer, and device 200 has a first light emitting layer and a second light emitting layer, the light emitting peaks of the first and second light emitting layers may be overlapping or cross-overlapping or non-overlapping. In the corresponding layers of device 200, materials similar to those described with respect to device 100 may be used. Fig. 2 provides one example of adding layers from the structure of device 100.
Detailed Description
The following examples are illustrative of the invention and are not intended to limit the scope of the invention.
In the description of the present invention, unless otherwise indicated, the meaning of "a plurality" is two or more; the orientation or positional relationship indicated by the terms "upper", "lower", etc. are based on the orientation or positional relationship shown in the drawings, are merely for convenience of description and to simplify the description, and are not indicative or implying that the apparatus or elements in question must have a specific orientation, be constructed and operated in a specific orientation, and therefore should not be construed as limiting the present invention.
The experimental methods used in the following examples are conventional methods unless otherwise specified. The experimental materials and related equipment used in the examples below, unless otherwise specified, are all commercially available, and the percentages, such as the percentages without otherwise specified, are all mass percentages.
The following examples are examples of the test apparatus and method for testing the performance of OLED materials and devices as follows:
OLED element performance detection conditions:
luminance and chromaticity coordinates: photoresearch PR-715 was tested using a spectrum scanner;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: NEWPORT 1931-C test was used.
Example 1
A process for preparing compound C626 comprising the steps of:
the first step: preparation of intermediate Int-1
20.0mmol of 4-bromocarbazole (sub-1), 24.0mmol of 1-fluoro-9-fluorenone (sub-2), 60.0mmol of anhydrous potassium carbonate and 60mL of DMF are mixed, the temperature is raised to 120 ℃ and stirred for reaction for 12 hours, the temperature is reduced to room temperature, 200mL of water is added, the filtration is carried out, a filter cake is washed by water, and the solid is separated and purified by a silica gel column to obtain a compound Int-1 as a yellow solid, and the yield is: 87%.
And a second step of: preparation of intermediate Int-2
Under the protection of nitrogen, 20.0mmol of Int-1 is dissolved in 50mL of dry THF, the temperature is reduced to 0 ℃,24.0mmol of 1M methyl magnesium bromide THF solution is added dropwise, the temperature is raised to room temperature, the reaction is stirred for 2 hours, 20mL of 2M dilute hydrochloric acid aqueous solution is added dropwise, the ethyl acetate is used for extraction, the organic phase is collected and dried, the filtration is carried out, the filtrate is concentrated and dried under reduced pressure, and the compound Int-2 is obtained by separation and purification by a silica gel column, yellow solid is obtained, and the yield is: 86%.
And a third step of: preparation of intermediate Int-3
Under the protection of nitrogen, 20.0mmol of Int-2 is dissolved in 60mL of dichloromethane, the temperature is reduced to 0 ℃, 30.0mmol of boron trifluoride diethyl etherate solution is added dropwise, the temperature is raised to room temperature, stirring reaction is carried out for 2 hours, 20mL of ice water is added, an organic phase is separated, the aqueous phase is extracted by dichloromethane, the organic phase is collected and dried, filtered, the filtrate is concentrated and dried under reduced pressure, and the compound Int-3 is obtained by separating and purifying by a silica gel column, and the yield is yellow solid: 90%.
Fourth step: preparation of Compound C626
Under the protection of nitrogen, 22.0mmol of compound Int-3 is dissolved in 80mL of dry toluene, and 20.0mmol of sub-3, 30.0mmol of tertiary sodium butoxide and 0.2mmol of Pd are added 2 (dba) 3 And 0.4mmol XantPhos, raise the temperature to 110 ℃ and stir and react for 12 hours, cool to room temperature, add 50mL of water, separate the organic phase, the aqueous phase is extracted with ethyl acetate, the organic phase is dried, concentrate and dry under reduced pressure, separate and purify with silica gel column, then recrystallise with toluene/ethyl acetate, get compound C626;
x=fr, pale yellow solid, yield 82%, MS (TOF): m/z=825.3209 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.08(1H,s)；7.92～7.86(6H,m)；7.75～7.71(2H,m)；7.61～7.58(1H,m)；7.56～7.50(5H,m)；7.48～7.39(7H,m)；7.36～7.29(5H,m)；7.27～7.18(7H,m)；7.16～7.14(1H,d)；7.08～7.05(1H,m)；6.97～6.94(1H,m)；2.43(3H,s)。
X＝C(CH 3 ) 2 Pale yellow solid, 85% yield, MS (TOF): m/z=703.3047 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.27(1H,s)；7.93～7.85(4H,m)；7.75～7.71(2H,m)；7.61～7.58(1H,m)；7.56～7.51(4H,m)；7.49～7.40(5H,m)；7.38～7.30(6H,m)；7.28～7.23(3H,m)；7.16～7.14(1H,d)；7.08～7.05(1H,m)；6.97～6.94(1H,m)；2.43(3H,s)；1.68(6H,s)。
X=ad, pale yellow solid, yield 83%, MS (TOF): m/z=795.3677 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.27(1H,s)；7.92～7.85(4H,m)；7.75～7.71(2H,m)；7.61～7.58(1H,m)；7.56～7.50(4H,m)；7.48～7.40(5H,m)；7.38～7.30(6H,m)；7.28～7.23(3H,m)；7.16～7.14(1H,d)；7.08～7.05(1H,m)；6.97～6.94(1H,m)；2.43(3H,s)；2.25～2.16(2H,m)；2.14～1.99(10H,m)；1.69～1.54(2H,m)。
Example 2
A process for preparing compound C679 comprising the steps of:
the first step: preparation of intermediate Int-4
Introducing nitrogen protection, 20.0mmol of Int-3' (prepared by the synthetic method of the example 1), 24.0mmol of triisopropyl borate and 60mL of dry THF, cooling to-78 ℃, dropwise adding 24.0mmol of 2.5M n-butyllithium n-hexane solution, stirring for reaction for 1 hour, heating to room temperature, dropwise adding 20mL of 3M dilute hydrochloric acid aqueous solution, separating an organic phase, extracting an aqueous phase by ethyl acetate, collecting the organic phase, drying, concentrating and drying under reduced pressure, adding 20mL of n-pentane for dispersion, filtering, washing a filter cake by n-pentane to obtain a compound Int-4, yellow solid and yield: 78%.
And a second step of: preparation of Compound C679
24.0mmol of compound Int-4 is dissolved in 60mL of toluene under the protection of nitrogen, 20.0mmol of sub-4, 60.0mmol of anhydrous sodium carbonate, 0.01mmol of Pd132, 30mL of ethanol and 30mL of water are added, the temperature is raised to reflux and stirring for reaction for 15 hours, the temperature is reduced to room temperature, 50mL of water is added, an organic phase is separated, the aqueous phase is extracted by ethyl acetate, the organic phase is dried, concentrated and dried under reduced pressure, and the compound C679 is obtained by separating and purifying by a silica gel column, and the yield is: 83%, MS (TOF): m/z=713.2711 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.96(1H,s)；8.78～8.73(4H,m)；8.47～8.44(1H,m)；8.06(1H,s)；7.96～7.94(1H,m)；7.86～7.84(1H,d)；7.74～7.71(1H,m)；7.57～7.50(6H,m)；7.48～7.34(9H,m)；7.29～7.24(3H,m)；7.17～7.14(1H,m)；7.11～7.06(3H,m)。
Example 3
Preparation of compound C732:
22.0mmol of Compound Int-3 (prepared by the method of example 1) is dissolved in 80mL of dry toluene under nitrogen protection, 20.0mmol of sub-5, 30.0mmol of sodium tert-butoxide and 0.2mmol of Pd are added 2 (dba) 3 And 0.4mmol of 10% tri-tert-butyl phosphorus toluene solution, heating to 100 ℃ and stirring for reaction for 12 hours, cooling to room temperature, adding 50mL of water, separating an organic phase, extracting the aqueous phase with ethyl acetate, drying the organic phase, concentrating and drying under reduced pressure, and separating and purifying by a silica gel column to obtain a compound C732, a yellow solid with a yield of 86%, MS (TOF): m/z=751.3053 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.43(1H,s)；7.97(1H,s)；7.94～7.85(5H,m)；7.56～7.51(3H,m)；7.45～7.39(4H,m)；7.37～7.32(4H,m)；7.29～7.21(7H,m)；7.19～7.14(4H,m)；7.11～7.02(6H,m)；6.98～6.95(2H,m)；6.92～6.89(1H,m)。
Examples 4 to 213
With reference to the synthetic methods analogous to examples 1 to 3 above, the following compounds were prepared:
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in the above embodiments, each x— is independently selected from one of the structures shown below:
* -and- (x) represents a bond.
Example 214
An organic electroluminescent device 100, the structure of which is shown in fig. 1, comprises a substrate 101, an anode layer 102, a hole injection layer 108, a hole transport layer 104, an electron blocking layer 105, a light emitting layer 106, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, a cathode layer 110, and a capping layer (CPL) or a photorefractive layer 111, and the device manufacturing method omitting the hole blocking layer 107 comprises the following steps:
1) The glass substrate coated with the ITO conductive layer is subjected to ultrasonic treatment in a cleaning agent for 80 minutes, rinsed in deionized water, ultrasonic treated in an acetone/ethanol mixed solvent for 80 minutes, baked in a clean environment until completely dried, irradiated by an ultraviolet light cleaning machine for 10 minutes, and bombarded on the surface by a low-energy cation beam.
2) Placing the above ITO glass substrate in vacuum chamber, and vacuumizing to less than 1×10 -5 Pa, depositing metallic silver as an anode layer on the ITO film, the thickness of the deposited film beingVapor deposition compounds HI01 and HI102 were used as hole injection layers, wherein HI102 was 3% by mass of HI01, and the vapor deposition film thickness was +.>
3) Continuously evaporating compound HTM as hole transport layer on the hole injection layer to obtain an evaporating film with a thickness of/>
4) The compounds of the present invention prepared in examples 1 to 213 were further vapor deposited on the hole transport layer to form an electron blocking layer, and the vapor deposited film had a thickness of
5) Continuously evaporating a compound PH011 as a main material and GD100 as a doping material on the electron blocking layer, wherein GD100 is 3% of the mass of the compound PH011, and the film thickness of the evaporation film is as an organic light-emitting layer
6) Continuously evaporating a layer of LiQ and ET06 on the organic light-emitting layer as an electron transmission layer, wherein the mass ratio of the LiQ to the ET06 is 50:50, and the thickness of the evaporated film is
7) Continuously evaporating a LiF layer on the electron transport layer to form an electron injection layer with an evaporating film thickness of
8) Evaporating metal magnesium and silver on the electron injection layer to form a transparent cathode layer, wherein the mass ratio of magnesium to silver is 1:10, and the film thickness of the evaporated film is
9) Vapor deposition of NPD (CAS: 123847-85-8) as CPL of the element on the transparent cathode layer, the vapor deposition film thickness beingThe OLED element provided by the invention is obtained.
The structure of the compound used in example 214 above was as follows:
example 215
An organic electroluminescent device 200, the structure of which is shown in fig. 2, comprises a substrate 201, an anode layer 202, a hole injection layer 208, a hole transport layer 204, a first light emitting layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second light emitting layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode layer 213. The device 200 may be prepared by sequentially depositing the layers described. Because the most common OLED device has one light emitting layer, and device 200 has a first light emitting layer and a second light emitting layer, the light emitting peaks of the first and second light emitting layers may be overlapping or cross-overlapping or non-overlapping. In the corresponding layers of device 200, materials similar to those described with respect to device 100 may be used.
Comparative example 1
By following a procedure similar to example 214, substituting the compound prepared in example 4) with B-1, comparative element 1 was obtained; the structural formula of B-1 is as follows:
comparative example 2
By following a procedure similar to example 214, substituting the compound prepared in example 4) with B-2, comparative element 2 was obtained; the structural formula of the B-2 is as follows:
the organic electroluminescent element prepared by the above process was subjected to the following performance test:
the driving voltage and current efficiency of the organic electroluminescent elements and the lifetime of the elements prepared in the above-described example 214, example 215, comparative example 1 and comparative example 2 were measured using a digital source meter and a luminance meter. Specifically, the luminance of the organic electroluminescent element was measured to reach 1000cd/m by increasing the voltage at a rate of 0.1V per second 2 The voltage at the time is the driving voltage, and the current density at the time is measured; the ratio of brightness to current density is the luminous efficiency; LT90% life test is as follows: using a luminance meter at 10000cd/m 2 The luminance decay of the organic electroluminescent element was measured to 9000cd/m while maintaining a constant current at luminance 2 Time in hours. The data listed in table 1 are relative data compared to comparative element 1.
TABLE 1 results of testing the performance of the elements
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As can be seen from Table 1The carbazole derivative of the invention is used as the material of the electron blocking layer to prepare the luminous element with the same current density of 10mA/cm 2 Under the condition that the driving voltage is lower than that of B-1, the luminous efficiency is high, the LT90% service life is excellent, and the carbazole derivative is an electron blocking layer material with excellent performance.
The carbazole derivative of the present invention is different from the compounds B-1 and B-2 of the comparative example in that the carbazole derivative of the present invention prevents rotation of the benzene ring after fixing one benzene of the indoloacridine to form the indenoindoloacridine, thereby reducing molecular steric hindrance, being superior to B-1 and B-2 in both molecular film formation and exciton blocking properties, and being more balanced in charge transport in the light emitting layer, and thus, the carbazole derivative of the present invention is more excellent in performance of the light emitting element.
While the invention has been described in detail in the foregoing general description and with reference to specific embodiments thereof, it will be apparent to one skilled in the art that modifications and improvements can be made thereto. Accordingly, such modifications or improvements may be made without departing from the spirit of the invention and are intended to be within the scope of the invention as claimed.
Claims (10)
1. The carbazole derivative is characterized by having a structural formula shown in a formula (I):
wherein,
R 1 selected from hydrogen, deuterium, substituted or unsubstituted C 1 -C 40 Alkyl, substituted or unsubstituted C 3 -C 40 Cycloalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamine group, substituted or unsubstituted C 2 -C 60 A group consisting of heteroaryl groups;
R 2 、R 3 、R 4 、R 5 each independently selected from the group consisting of hydrogen, deuterium, cyano, substituted or unsubstituted C 1 -C 40 Alkyl, substituted or unsubstituted C 3 -C 40 Cycloalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamine group, substituted or unsubstituted C 2 -C 60 A heterocyclic aryl group or a group represented by formula (II); adjacent two or more R 2 、R 3 、R 4 、R 5 Optionally joined or fused to form a substituted or unsubstituted ring;
the structural formula of formula (II) is as follows:
Ar 1 、Ar 2 each independently selected from the group consisting of substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamine groups, or substituted or unsubstituted C 2 -C 60 A group consisting of heteroaryl groups; ar (Ar) 1 And Ar is a group 2 Optionally joined or fused to form a substituted or unsubstituted ring;
m is selected from integers of 0 to 5;
L 1 selected from single bonds, substituted or unsubstituted C 6 -C 60 Arylene of (2), or substituted or unsubstituted C 2 -C 60 Heteroarylene;
and- (II) represents a bond between formula (II) and formula (I).
2. The carbazole derivative according to claim 1, characterized in that the carbazole derivative is selected from the group consisting of the structures shown below:
wherein R is 1 ～R 5 、L 1 、Ar 1 、Ar 2 And m has the same meaning as defined in claim 1.
3. Carbazole derivative according to any one of claims 1 or 2, characterized in that Ar 1 、Ar 2 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylene, substituted or unsubstituted triphenylene, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted indolyl, or substituted or unsubstituted carbolinyl;
R 1 selected from the group consisting of hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, and furanyl, dibenzofuranyl, benzothienyl, dibenzothienyl, naphthyl, phenanthryl, anthracenyl, fluorenyl, spirobifluorenyl, or carbazolyl;
R 2 、R 3 、R 4 、R 5 each independently selected from the group consisting of hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted benzofuranA group consisting of a group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted carboline group.
4. A carbazole derivative according to any one of claims 1 to 3, characterized in that R 2 、R 3 、R 4 、R 5 Each independently selected from hydrogen, deuterium, or a group of formula (II).
5. Carbazole derivative according to claim 1, characterized in that the L 1 Selected from a single bond or a group consisting of groups III-1 to III-23:
wherein the dotted line represents the attachment site of the group;
and m is selected from 0, 1 or 2.
6. The carbazole derivative according to any one of claims 1 to 5, characterized in that the carbazole derivative has a structural formula selected from the group consisting of C600 to C812:
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wherein each x— is independently selected from one of the following structures:
* -and- (x) represents a bond.
7. An organic electroluminescent material, characterized in that its raw material comprises the carbazole derivative as claimed in any one of claims 1 to 6.
8. Use of the carbazole derivative as claimed in any one of claims 1 to 6 for the preparation of organic electroluminescent elements.
9. An organic electroluminescent element, characterized in that it comprises: a first electrode, a second electrode, a capping layer or a light refracting layer, and one or more organic layers disposed between the first electrode and the second electrode; at least one of the organic layer and the light refracting layer comprises the carbazole derivative according to any one of claims 1 to 6.
10. The organic electroluminescent element according to claim 9, wherein the organic layer comprises a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, or an electron blocking layer;
preferably, the light-emitting layer, hole-transporting layer or electron blocking layer comprises the carbazole derivative according to any one of claims 1 to 6.
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