WO2018058497A1 - Composé organique et dispositif électronique comprenant une couche organique comprenant le composé organique - Google Patents
Composé organique et dispositif électronique comprenant une couche organique comprenant le composé organique Download PDFInfo
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- WO2018058497A1 WO2018058497A1 PCT/CN2016/100996 CN2016100996W WO2018058497A1 WO 2018058497 A1 WO2018058497 A1 WO 2018058497A1 CN 2016100996 W CN2016100996 W CN 2016100996W WO 2018058497 A1 WO2018058497 A1 WO 2018058497A1
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- Prior art keywords
- substituted
- unsubstituted
- aryl
- group
- heteroaryl
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 50
- 239000012044 organic layer Substances 0.000 title claims abstract description 22
- 239000010410 layer Substances 0.000 claims description 32
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 25
- 125000006753 (C1-C60) heteroaryl group Chemical group 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000003277 amino group Chemical group 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 11
- 229910052805 deuterium Inorganic materials 0.000 claims description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000005110 aryl thio group Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 230000005525 hole transport Effects 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 238000002347 injection Methods 0.000 claims description 8
- 239000007924 injection Substances 0.000 claims description 8
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 7
- 125000006762 (C1-C60) heteroarylene group Chemical group 0.000 claims description 7
- 125000006761 (C6-C60) arylene group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 125000005842 heteroatom Chemical group 0.000 description 15
- -1 benzofluorenyl Chemical group 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 125000001072 heteroaryl group Chemical group 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000000523 sample Substances 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 125000003636 chemical group Chemical group 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 238000002411 thermogravimetry Methods 0.000 description 5
- 0 C*(C=C1)c2c1c(*)c(*)c(N[C@]1C(C([Rh](C)C)=O)=C*N(*)*)c2C1c1ccccc1 Chemical compound C*(C=C1)c2c1c(*)c(*)c(N[C@]1C(C([Rh](C)C)=O)=C*N(*)*)c2C1c1ccccc1 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000002952 polymeric resin Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229920003002 synthetic resin Polymers 0.000 description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 2
- QRXMUCSWCMTJGU-UHFFFAOYSA-N 5-bromo-4-chloro-3-indolyl phosphate Chemical compound C1=C(Br)C(Cl)=C2C(OP(O)(=O)O)=CNC2=C1 QRXMUCSWCMTJGU-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 238000003775 Density Functional Theory Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 239000007832 Na2SO4 Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002475 indoles Chemical class 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000007764 slot die coating Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 1
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 1
- OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical group C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 description 1
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-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
- GPTAKAWFMITEOL-UHFFFAOYSA-N 2-(4-bromophenyl)-1-phenylethanone Chemical compound C1=CC(Br)=CC=C1CC(=O)C1=CC=CC=C1 GPTAKAWFMITEOL-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
- QRMLAMCEPKEKHS-UHFFFAOYSA-N 9,9-dimethyl-n-(4-phenylphenyl)fluoren-2-amine Chemical compound C1=C2C(C)(C)C3=CC=CC=C3C2=CC=C1NC(C=C1)=CC=C1C1=CC=CC=C1 QRMLAMCEPKEKHS-UHFFFAOYSA-N 0.000 description 1
- GJWBRYKOJMOBHH-UHFFFAOYSA-N 9,9-dimethyl-n-[4-(9-phenylcarbazol-3-yl)phenyl]-n-(4-phenylphenyl)fluoren-2-amine Chemical compound C1=C2C(C)(C)C3=CC=CC=C3C2=CC=C1N(C=1C=CC(=CC=1)C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C(C=C1)=CC=C1C1=CC=CC=C1 GJWBRYKOJMOBHH-UHFFFAOYSA-N 0.000 description 1
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 1
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 description 1
- XYTJVTXOOLTWST-UHFFFAOYSA-N CC1(C)c(cc(cc2)N(c(cc3)ccc3-c(cc3)ccc3-c3c(-c4ccccc4)[n](C)c4ccc(cccc5)c5c34)c3ccc4-c5ccccc5C(C)(C)c4c3)c2-c2c1cccc2 Chemical compound CC1(C)c(cc(cc2)N(c(cc3)ccc3-c(cc3)ccc3-c3c(-c4ccccc4)[n](C)c4ccc(cccc5)c5c34)c3ccc4-c5ccccc5C(C)(C)c4c3)c2-c2c1cccc2 XYTJVTXOOLTWST-UHFFFAOYSA-N 0.000 description 1
- MIKXIFCOZCCXCW-UHFFFAOYSA-N CC1(C)c(cc(cc2)N(c(cc3)ccc3-c3c(-c4ccccc4)[n](C)c4ccc(cccc5)c5c34)c(cc3)cc(C4(C)C)c3-c3c4cccc3)c2-c2c1cccc2 Chemical compound CC1(C)c(cc(cc2)N(c(cc3)ccc3-c3c(-c4ccccc4)[n](C)c4ccc(cccc5)c5c34)c(cc3)cc(C4(C)C)c3-c3c4cccc3)c2-c2c1cccc2 MIKXIFCOZCCXCW-UHFFFAOYSA-N 0.000 description 1
- YUABXEZZNOCWHE-UHFFFAOYSA-N CC1(C)c(cc(cc2)N(c(cc3)ccc3-c3c(-c4ccccc4)[n](C)c4ccc(cccc5)c5c34)c(cc3)ccc3-c3ccccc3)c2-c2c1cccc2 Chemical compound CC1(C)c(cc(cc2)N(c(cc3)ccc3-c3c(-c4ccccc4)[n](C)c4ccc(cccc5)c5c34)c(cc3)ccc3-c3ccccc3)c2-c2c1cccc2 YUABXEZZNOCWHE-UHFFFAOYSA-N 0.000 description 1
- 101100394073 Caenorhabditis elegans hil-1 gene Proteins 0.000 description 1
- 101100506090 Caenorhabditis elegans hil-2 gene Proteins 0.000 description 1
- 238000006783 Fischer indole synthesis reaction Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 125000002078 anthracen-1-yl 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
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000005284 basis set Methods 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 150000001602 bicycloalkyls Chemical group 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 238000004807 desolvation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- FYSSYOCJFZSKNW-UHFFFAOYSA-N hydron;naphthalen-1-ylhydrazine;chloride Chemical compound [Cl-].C1=CC=C2C(N[NH3+])=CC=CC2=C1 FYSSYOCJFZSKNW-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 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
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 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
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- LCSMGMWMTSWXDD-UHFFFAOYSA-N n-(9,9-dimethylfluoren-2-yl)-9,9-dimethylfluoren-2-amine Chemical compound C1=CC=C2C(C)(C)C3=CC(NC4=CC=C5C6=CC=CC=C6C(C5=C4)(C)C)=CC=C3C2=C1 LCSMGMWMTSWXDD-UHFFFAOYSA-N 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 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
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000008521 reorganization Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000758 substrate 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
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000002207 thermal evaporation 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
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/60—Naphtho [b] pyrroles; Hydrogenated naphtho [b] pyrroles
-
- H—ELECTRICITY
- 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
-
- 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
Definitions
- the present invention relates to organic compounds, and an electronic device comprising an organic layer comprising the organic compounds.
- OLEDs are display devices that employ stacks of organic layers including electron transport layers (ETLs) and hole transport layers (HTLs) .
- ETLs electron transport layers
- HTLs hole transport layers
- OLEDs have drawn much attention in recent years as one of the most promising next-generation displays because of their many performance advantages including light weight, energy saving and high contrast.
- the present invention provides organic compounds having a structure represented by Formula (1) :
- R 1 , R 2 , R 3 , and R 4 are each independently selected from the group consisting of hydrogen, deuterium ( “D” ) , a substituted or unsubstituted C 1 -C 50 alkyl, a substituted or unsubstituted C 1 -C 50 alkoxy, a substituted or unsubstituted C 1 -C 50 alkoxycarbonyl, a substituted or unsubstituted C 6 -C 60 aryl, a substituted or unsubstituted C 1 -C 60 heteroaryl, a substituted or unsubstituted C 6 -C 60 aryloxy, a substituted or unsubstituted C 6 -C 50 arylthio, a halogen, a cyano, a hydroxyl, and a carbonyl;
- R 5 is a substituted or unsubstituted C 1 -C 30 alkyl, a substituted or unsubstituted C 3 -C 50 cycloalkyl, a substituted or unsubstituted C 6 -C 60 aryl, or a substituted or unsubstituted C 1 -C 60 heteroaryl;
- R a , R b , R a ’, and R b ’ are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50 alkyl, a substituted or unsubstituted C 3 -C 50 cycloalkyl, a substituted or unsubstituted C 6 -C 60 aryl, and a substituted or unsubstituted C 1 -C 60 heteroaryl;
- R 6 and R 7 are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50 alkyl, a substituted or unsubstituted C 1 -C 50 alkoxy, a substituted or unsubstituted C 1 -C 50 alkoxycarbonyl, a substituted or unsubstituted C 6 -C 60 aryl, a substituted or unsubstituted C 1 -C 60 heteroaryl, a substituted or unsubstituted C 6 -C 60 aryloxy, a substituted or unsubstituted C 6 -C 50 arylthio, a halogen, a cyano, a hydroxyl, a carbonyl, and a substituted amino group having the structure of wherein Ar 1 and Ar 2 are each independently selected from the group consisting of a substituted or unsubstituted C 6 -C 60 aryl and a substituted or unsub
- X 1 and X 2 are each independently a chemical bond, or selected from the group consisting of a substituted or unsubstituted C 1 -C 50 alkylene, a substituted or unsubstituted C 3 -C 50 cycloalkylene, a substituted or unsubstituted C 6 -C 60 arylene, and a substituted or unsubstituted C 1 -C 60 heteroarylene; and X may form one or more fused rings with the adjacent phenyl ring.
- a substituted or unsubstituted C 5 -C 50 cycloalkyl is selected from the group consisting of a substituted or unsubstituted C 5 -C 50 cycloalkyl, a substituted or unsubstituted C 6 -C 60 aryl, and a substituted or unsubstituted C 1 -C 60 heteroaryl.
- the present invention further provides an electronic device comprising an organic layer comprising the organic compounds.
- the organic compounds of the present invention have the structure represented by Formula (1) :
- R 1 , R 2 , R 3 , and R 4 are each independently selected from the group consisting of hydrogen; deuterium ( “D” ) ; a substituted or unsubstituted C 1 -C 50 alkyl, C 1 -C 30 alkyl, C 1 -C 20 alkyl, or C 1 -C 10 alkyl; a substituted or unsubstituted C 1 -C 50 alkoxy, C 1 -C 30 alkoxy, C 1 -C 20 alkoxy, or C 1 -C 10 alkoxy; a substituted or unsubstituted C 1 -C 50 alkoxycarbonyl, C 1 -C 30 alkoxycarbonyl, C 1 -C 20 alkoxycarbonyl, or C 1 -C 10 alkoxycarbonyl; a substituted or unsubstituted C 6 -C 60 aryl, C 6 -C 30 aryl, C 6 -C 20 aryl, or C 6 -C
- R 1 , R 2 , R 3 and R 4 are each independently selected from hydrogen, a halogen, a substituted or unsubstituted C 1 -C 3 alkyl, and a substituted or unsubstituted C 6 -C 60 aryl. More preferably, R 1 , R 2 , R 3 and R 4 are each independently selected from hydrogen, F, methyl, phenyl, naphthyl, and biphenyl.
- At least two of R 1 through R 4 are hydrogen. Preferably, all R 1 through R 4 are hydrogen.
- R 5 is a substituted or unsubstituted C 1 -C 30 alkyl, C 1 -C 20 alkyl, C 1 -C 10 alkyl, C 1 -C 5 alkyl, or C 1 -C 3 alkyl; a substituted or unsubstituted C 3 -C 50 cycloalkyl, C 4 -C 30 cycloalkyl, C 4 -C 20 cycloalkyl, or C 4 -C 12 cycloalkyl; a substituted or unsubstituted C 6 -C 60 aryl, C 6 -C 30 aryl, C 6 -C 20 aryl, or C 6 -C 12 aryl; or a substituted or unsubstituted C 1 -C 60 heteroaryl, C 1 -C 30 heteroaryl, C 2 -C 20 heteroaryl, or C 4 -C 12 heteroaryl.
- R 5 is selected from -CH 3 , -CH 2 CH 3
- R a , R b , R a ’, R b ’ are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50 alkyl, a substituted or unsubstituted C 3 -C 50 cycloalkyl, a substituted or unsubstituted C 6 -C 60 aryl, and a substituted or unsubstituted C 1 -C 60 heteroaryl.
- R 6 and R 7 are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C 1 -C 50 alkyl, C 1 -C 30 alkyl, C 1 -C 20 alkyl, or C 1 -C 10 alkyl; a substituted or unsubstituted C 1 -C 50 alkoxy, C 1 -C 30 alkoxy, C 1 -C 20 alkoxy, or C 1 -C 10 alkoxy; a substituted or unsubstituted C 1 -C 50 alkoxycarbonyl, C 1 -C 30 alkoxycarbonyl, C 1 -C 20 alkoxycarbonyl, or C 1 -C 10 alkoxycarbonyl; a substituted or unsubstituted C 6 -C 60 aryl, C 6 -C 30 aryl, C 6 -C 20 aryl, or C 6 -C 12 aryl; a substituted or unsubstituted C 1
- Ar 1 and Ar 2 are each independently selected from the group consisting of a substituted or unsubstituted C 6 -C 60 aryl, C 6 -C 30 aryl, C 6 -C 20 aryl, or C 6 -C 15 aryl; and a substituted or unsubstituted C 1 -C 60 heteroaryl, C 1 -C 30 heteroaryl, C 2 -C 20 heteroaryl, or C 4 -C 12 heteroaryl.
- Ar 1 and Ar 2 are each independently a substituted or unsubstituted C 6 -C 60 aryl. More preferably, Ar 1 and Ar 2 are each independently a substituted or unsubstituted C 12 -C 30 aryl.
- R 6 and R 7 are the substituted amino group.
- one of R 6 and R 7 is the substituted amino group, and the other one of R 6 and R 7 is selected from hydrogen, a halogen, and a substituted or unsubstituted C 6 -C 60 aryl.
- the substituted amino group is selected from the following structures represented by Formula (a) through Formula (c) :
- Ar 3 and Ar 4 are each independently an unsubstituted C 6 -C 60 aryl
- Ar 5 through Ar 7 are each independently an unsubstituted C 6 -C 40 aryl
- Ar 8 through Ar 11 are each independently an unsubstituted C 6 -C 30 aryl
- L 1 through L 3 are each independently selected from the group consisting of a substituted or unsubstituted C 6 -C 60 arylene and a substituted or unsubstituted C 1 -C 60 heteroarylene.
- Ar 3 through Ar 11 may be each independently an unsubstituted C 6 -C 30 aryl, C 6 -C 20 aryl, C 6 -C 15 aryl, or C 6 -C 12 aryl.
- Suitable examples of the substituted amino groups comprise the following structures (1) through (6) :
- a substituted or unsubstituted C 5 -C 50 cycloalkyl is selected from the group consisting of a substituted or unsubstituted C 5 -C 50 cycloalkyl, a substituted or unsubstituted C 6 -C 60 aryl, and a substituted or unsubstituted C 1 -C 60 heteroaryl.
- X 1 and X 2 may be the same or different.
- X 1 and X 2 are each independently a chemical bond, or selected from the group consisting of a substituted or unsubstituted C 1 -C 50 alkylene, a substituted or unsubstituted C 3 -C 50 cycloalkylene, a substituted or unsubstituted C 6 -C 60 arylene, and a substituted or unsubstituted C 1 -C 60 heteroarylene.
- X 1 or X 2 is a chemical bond
- R 6 or R 7 is directly linked to its adjacent phenyl ring through X 1 or X 2 .
- X 1 or X 2 may form one or more fused rings with the adjacent phenyl ring.
- Suitable examples of X l or X 2 comprise
- the organic compounds of the present invention have the structure represented by Formula (2) :
- organic compounds of the present invention have the structure represented by Formula (3) or (4) :
- organic compounds of the present invention have the structure represented by Formula (5) or (6) :
- Suitable examples of the organic compounds are selected from the following structures (7) through (30) :
- the organic compounds of the present invention may have a molecular weight of 500 g/mole or more, 600 g/mole or more, or even 700 g/mole or more, and at the same time, 1,000 g/mole or less, 900 g/mole or less, or even 800 g/mole or less.
- the organic compounds of the present invention may have a glass transition temperature (Tg) of 110 °C or higher, 130 °C or higher, or 150 °C or higher, and at the same time, 250 °C or lower, 220 °C or lower, or even 200 °C or lower, as measured according to the test method described in the Examples section below.
- Tg glass transition temperature
- the organic compounds of the present invention may have a decomposition temperature (Td, 5%weight loss) of 300 °C or higher, 350 °C or higher, or 400 °C or higher, and at the same time, 650 °C or lower, 600 °C or lower, or even 550 °C or lower, as measured according to the test method described in the Examples section below.
- Td decomposition temperature
- the organic compounds of the present invention may be prepared as shown in Scheme 1 below.
- An arylhydrazine hydrochloride may react with a diphenylethanone derivative Structure A through a Fischer indole synthesis reaction to give an indole derivative of Structure B.
- the indole derivative may react with a halogen containing compound with the structure of R 5 Y, wherein R 1 through R 5 , X l and X 2 , Ar 1 and Ar 2 , R a , R b , R a ’, and R b ’, and are as previously defined with reference to Formula (1) and Y is a halogen such as F, Cl, Br or I, and preferably Br or I.
- the resultant compound of Structure C may undergo a Buchwald-Hartwig coupling reaction and Formula (1) of the present invention could be obtained.
- the organic compounds of the present invention may be used in organic layers including hole transport layers (HTL) , electron transport layers (ETL) , hole injection layers (HIL) , charge blocking layers, charge generation layers, and emissive layers (EML) in electronic devices.
- the organic layer is a hole transport layer or a hole injection layer.
- charge blocking layer herein refers to certain layers of structures blocking charge transfer to improve efficiency.
- charge generation layer herein refers to certain layers of structures which can generate charges.
- Organic compounds of the present invention may be used in electronic devices including organic photovoltaic cells, organic field effect transistors (OFETs) , and light emitting devices.
- OFETs organic field effect transistors
- Light emitting devices are electronic devices emitting lights when electrical currents were applied across two electrodes in the devices.
- the electronic device of the present invention may comprise an anode, a cathode, and at least one organic layer interposed between the anode and the cathode. At least one of the organic layers comprises at least one of the organic compounds of the present invention.
- the organic layer can be a charge transfer layer that can transport charge carrying moieties, either holes or electrons.
- the organic layer may be a hole transport layer, an emissive layer, an electron transport layer, or a hole injection layer.
- the organic layer is a hole transport layer or a hole injection layer.
- the organic layer may comprise one or more “dopants” .
- Dopants are impurities deliberately added in small amounts to a pure substance (i.e., a “host” ) to alter its properties such as conductivity and emitting property. It has the effect of shifting the Fermi level of the original material (i.e., the “host” ) , which results in a material with predominantly negative (n-type) or positive (p-type) charge carriers depending on the dopant variety.
- the organic layer comprising the organic compounds of the present invention may be prepared by evaporative vacuum deposition or solution process such as spin coating, slot die coating and ink-jet printing.
- the organic compounds of the present invention may be a part of polymer resin of Mn higher than 6,000 Dalton.
- the polymer resin can be synthesized by a mixture of the organic compounds of the present invention, where the concentration of individual monomers can vary from 0.1%to 99.9%.
- the polymer resin can be deposited using spin coating, slot die coating or ink-jet printing.
- aryl refers to an organic radical derived from aromatic hydrocarbon by the removal of one hydrogen atom therefrom.
- An aryl group may be a monocyclic and/or fused ring system each ring of which suitably contains from 4 to 6, preferably from 5 or 6 atoms. Structures wherein two or more aryl groups are combined through single bond (s) are also comprised.
- aryls comprise phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, benzofluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphtacenyl, fluoranthenyl and the like.
- the naphthyl may be 1-naphthyl or 2-naphthyl.
- the anthryl may be 1-anthryl, 2-anthryl or 9-anthryl.
- the fluorenyl may be any one of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
- substituted aryl refers to an aryl in which at least one hydrogen atom is substituted with a heteroatom or a chemical group containing at least one heteroatom.
- Heteroatoms comprise O, N, P and S.
- the heteroaryl may be a 5-or 6-membered monocyclic heteroaryl or a polycyclic heteroaryl which is fused with one or more benzene ring (s) , and may be partially saturated.
- the structures having one or more heteroaryl group (s) bonded through a single bond are also comprised.
- the heteroaryl groups comprise divalent aryl groups of which the heteroatoms are oxidized or quarternized to form N-oxides, quaternary salts, or the like.
- Specific examples comprise monocyclic heteroaryl groups, such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl; polycyclic heteroaryl groups, such as benzofuranyl, fluoreno [4, 3-b] benzofuranyl, benzothiophenyl, fluoreno [4, 3-b] benzothiophenyl, isobenzofur
- substituted heteroaryl refers to a heteroaryl in which at least one hydrogen atom is substituted with a heteroatom or a chemical group containing at least one heteroatom.
- Heteroatoms comprise O, N, P and S.
- hydrocarbyl refers to a chemical group containing only hydrogen and carbon atoms.
- Alkyl, ” and other substituents containing “alkyl” moiety comprises both linear and branched species. Examples of alkyls comprise methyl, ethyl, propyl, iso-propyl, butyl, iso-butyl, tert-butyl, pentyl, and hexyl.
- substituted alkyl refers to an alkyl in which at least one hydrogen atom is substituted with a heteroatom or a chemical group containing at least one heteroatom.
- Heteroatoms comprise O, N, P and S.
- cycloalkyl refers to a monocyclic hydrocarbon and a polycyclic hydrocarbon such as substituted or unsubstituted adamantyl, and substituted or unsubstituted C 7 -C 30 bicycloalkyl.
- the triplet energies are determined as the difference between the total energy of the optimized triplet state and the optimized singlet state.
- a procedure as described in Lin, B. C et al., J. Phys. Chem. A 2003, 107, 5241-5251, is applied to calculate the reorganization energy of each molecule, with which as the indicator of electron and hole mobility.
- DSC Differential scanning calorimetry
- DSC measurements were carried out on Q2000 differential scanning calorimeter of TA Instruments at a scan rate of 10 °C/min under N 2 atmosphere for all cycles. Each sample (about 7-10 mg) was scanned from room temperature to 300 °C (first heating scan) , cooled to -60 °C, and then reheated to 300 °C (second heating scan) . Tg was measured on the second heating scan. Data analysis was performed using Universal Analysis 2000 software of TA Instruments. The Tg value was calculated using an “onset-at-inflection” methodology.
- TGA measurements were carried out on TGA-Q500 thermo gravimetric analyzer of TA Instruments under N 2 atmosphere. Each sample (about 7-10 mg) was weighed in a platinum standard plate and loaded into the instrument. Each sample was first heated to 60 °Cand equilibrated for 30 minutes to remove solvent residues in the sample. Then the sample was cooled to 30 °C. The temperature was ramped from 30 °C to 600 °C with 10 °C/min rate and the weight change was recorded to determine the decomposition temperature (Td) of the sample. The temperature-weight % (T-Wt %) curve was obtained by TGA scan. The temperature at the 5 %weight loss was determined as Td.
- sample was dissolved in tetrahydrofuran (THF) at around 0.6 mg/mL. 5 ⁇ L sample solution was injected on an Agilent 1220 HPLC/G6224A time-of-flight mass spectrometer. The following analysis conditions were used:
- MS conditions Capillary Voltage: 3500 kV (Pos) ; Mode: Pos; Scan: 100-2000 amu; Rate: 1 s/scan; and Desolvation temperature: 300 °C.
- Each sample was dissolved in THF at around 0.6 mg/mL.
- the sample solution was at last filtrated through a 0.45 ⁇ m syringe filter and 5 ⁇ L of the filtrate was injected to HPLC system.
- the following analysis conditions were used:
- Structure C1 In a three-neck flask, Structure B1 (1.0 mmol, 398 g/mol, 398 mg) was added into N, N-Dimethylacetamide (DMA) (20 mL) , and then cooled to 0 °C. NaH (1.5 mmol, 24 g/mol, 36 mg) was added into the solution at 0 °C. After 30 mins, MeI (1.5 mmol, 142 g/mol, 213 mg) was added and TLC was utilized to monitor the reaction. After completion of the reaction, alcohol was added to quench the reaction and then DI water (30 mL) was added.
- DMA N, N-Dimethylacetamide
- Structure 7 In a 100 mL three-neck flask, Structure C1 obtained above (412 mg, 1.0 mmol, 412 g/mol) , N- ( [1, 1'-biphenyl] -4-yl) -9, 9-dimethyl-9H-fluoren-2-amine (398 mg, 1.1 mmol, 361.5 g/mol) , NaOBu -t (115 mg, 1.2 mmol, 96 g/mol) , X-Phos (24 mg, 5%mmol, 476.7 g/mol) and Pd (OAc) 2 (11 mg, 5%mmol, 224.5 g/mol) were added into Toluene (30 mL) , and the solution was stirred at 110 °C under N 2 atmosphere overnight.
- Structure 9 In a 100 mL three-neck flask, Structure C1 (412 mg, 1.0 mmol, 412 g/mol) , bis (9, 9-dimethyl-9H-fluoren-2-yl) amine (442 mg, 1.1 mmol, 401.5 g/mol) , NaOBu -t (115 mg, 1.2 mmol, 96 g/mol) , X-Phos (24 mg, 5%mmol, 476.7 g/mol) and Pd (OAc) 2 (11 mg, 5%mmol, 224.5 g/mol) were added into Toluene (30 mL) , and the solution was stirred at 110 °C under N 2 atmosphere overnight.
- An OLED device containing organic compound Structure 7 or 9 as the hole transport layer was fabricated by thermally depositing organic layers, from bottom to top, electron injection layer (EIL) , electron transport layer (ETL) , emitting material layer (EML) , hole transport layer (HTL) , and hole injection layer (HIL1 and HIL2) , onto an indium tin oxide (ITO) coated glass substrate that served as an anode, and topped with an aluminum cathode.
- EIL electron injection layer
- ETL electron transport layer
- EML emitting material layer
- HTL hole transport layer
- HIL1 and HIL2 hole injection layer
- Thermal deposition was conducted by chemical vapor deposition in a vacuum chamber with a base pressure of ⁇ 10 -7 torr. The deposition rates of organic layers were maintained at 0.1-0.05 nm/s.
- the aluminum cathode was deposited at 0.5 nm/s.
- the active area of the OLED device was “3 mm x 3 mm. ”
- Organic materials used in organic layers were all purified by sublimation before deposition, and were placed inside the vacuum chamber until it reached 10 -6 torr. To evaporate each material, a controlled current was applied between the anode and the cathode to raise the temperature to keep the constant evaporation rate of 1A/sfor each organic material.
- a comparative OLED device containing N- ( [1, 1'-biphenyl] -4-yl) -9, 9-dimethyl-N- (4- (9-phenyl-9H-carbazol-3-yl) phenyl) -9H-fluoren-2-amine ( “HTL-C” ) as the hole transport layer was prepared with the similar procedure described above.
- J-V-L current density-voltage-luminance
- the inventive OLED devices had higher luminous efficiencies at a same or lower driving voltage compared to those of Comparative Device (25.0%higher for Structure 7 and 14.6%higher for Structure 9) .
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Abstract
L'invention concerne des composés organiques appropriés pour des couches organiques de dispositifs électroniques qui présentent une faible tension de commande et un rendement lumineux élevé.
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Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104725296A (zh) * | 2013-12-24 | 2015-06-24 | 北京鼎材科技有限公司 | 吲哚类衍生物及其在有机电致发光领域中的应用 |
KR20150121626A (ko) * | 2014-04-21 | 2015-10-29 | (주)피엔에이치테크 | 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자 |
KR20150131700A (ko) * | 2014-05-16 | 2015-11-25 | (주)피엔에이치테크 | 유기발광 화합물 및 이를 포함하는 유기전계발광소자 |
KR20150133097A (ko) * | 2014-05-19 | 2015-11-27 | (주)피엔에이치테크 | 유기발광 화합물 및 이를 포함하는 유기전계발광소자 |
WO2016021923A2 (fr) * | 2014-08-04 | 2016-02-11 | 주식회사 동진쎄미켐 | Nouveau composé et dispositif électroluminescent organique le contenant |
WO2016060463A2 (fr) * | 2014-10-14 | 2016-04-21 | 주식회사 동진쎄미켐 | Nouveau composé et élément électroluminescent organique comprenant le nouveau composé |
WO2016101865A1 (fr) * | 2014-12-26 | 2016-06-30 | Dow Global Technologies Llc | Composés organiques et dispositif électronique comprenant une couche organique comprenant des composés organiques |
-
2016
- 2016-09-30 WO PCT/CN2016/100996 patent/WO2018058497A1/fr active Application Filing
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104725296A (zh) * | 2013-12-24 | 2015-06-24 | 北京鼎材科技有限公司 | 吲哚类衍生物及其在有机电致发光领域中的应用 |
KR20150121626A (ko) * | 2014-04-21 | 2015-10-29 | (주)피엔에이치테크 | 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자 |
KR20150131700A (ko) * | 2014-05-16 | 2015-11-25 | (주)피엔에이치테크 | 유기발광 화합물 및 이를 포함하는 유기전계발광소자 |
KR20150133097A (ko) * | 2014-05-19 | 2015-11-27 | (주)피엔에이치테크 | 유기발광 화합물 및 이를 포함하는 유기전계발광소자 |
WO2016021923A2 (fr) * | 2014-08-04 | 2016-02-11 | 주식회사 동진쎄미켐 | Nouveau composé et dispositif électroluminescent organique le contenant |
WO2016060463A2 (fr) * | 2014-10-14 | 2016-04-21 | 주식회사 동진쎄미켐 | Nouveau composé et élément électroluminescent organique comprenant le nouveau composé |
WO2016101865A1 (fr) * | 2014-12-26 | 2016-06-30 | Dow Global Technologies Llc | Composés organiques et dispositif électronique comprenant une couche organique comprenant des composés organiques |
WO2016101908A1 (fr) * | 2014-12-26 | 2016-06-30 | Dow Global Technologies Llc | Composés organiques et dispositif électronique comprenant une couche organique comprenant des composés organiques |
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