CN109535189A - A kind of boracic organic compound and its application in organic electroluminescence device - Google Patents
A kind of boracic organic compound and its application in organic electroluminescence device Download PDFInfo
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- CN109535189A CN109535189A CN201710907099.7A CN201710907099A CN109535189A CN 109535189 A CN109535189 A CN 109535189A CN 201710907099 A CN201710907099 A CN 201710907099A CN 109535189 A CN109535189 A CN 109535189A
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- 238000005401 electroluminescence Methods 0.000 title claims abstract description 12
- 150000002894 organic compounds Chemical class 0.000 title claims description 22
- 238000006467 substitution reaction Methods 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- 125000001118 alkylidene group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000002347 injection Methods 0.000 claims description 6
- 239000007924 injection Substances 0.000 claims description 6
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 6
- -1 9,9- dimethyl fluorenyl Chemical group 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 230000005540 biological transmission Effects 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 229910052711 selenium Inorganic materials 0.000 claims description 4
- YRFKHKBUMKFMAU-UHFFFAOYSA-N 1,2-diphenylacridine Chemical class C1=CC=CC=C1C1=CC=C(N=C2C(C=CC=C2)=C2)C2=C1C1=CC=CC=C1 YRFKHKBUMKFMAU-UHFFFAOYSA-N 0.000 claims description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 230000004888 barrier function Effects 0.000 claims description 2
- 230000000903 blocking effect Effects 0.000 claims description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 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
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000001644 phenoxazinyl group Chemical class C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001424 substituent group Chemical group 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
- 238000006664 bond formation reaction Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 69
- 239000000463 material Substances 0.000 abstract description 53
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052796 boron Inorganic materials 0.000 abstract description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 93
- 239000010410 layer Substances 0.000 description 65
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 54
- 230000015572 biosynthetic process Effects 0.000 description 33
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 32
- 238000003786 synthesis reaction Methods 0.000 description 32
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
- 229910052757 nitrogen Inorganic materials 0.000 description 27
- 229910002027 silica gel Inorganic materials 0.000 description 26
- 239000000741 silica gel Substances 0.000 description 26
- 229960001866 silicon dioxide Drugs 0.000 description 26
- 230000000694 effects Effects 0.000 description 21
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- 239000007787 solid Substances 0.000 description 17
- 238000012800 visualization Methods 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000012298 atmosphere Substances 0.000 description 16
- 238000001816 cooling Methods 0.000 description 16
- 239000000706 filtrate Substances 0.000 description 16
- 238000001914 filtration Methods 0.000 description 16
- 238000010992 reflux Methods 0.000 description 16
- 238000005070 sampling Methods 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 238000004770 highest occupied molecular orbital Methods 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000002019 doping agent Substances 0.000 description 11
- 238000009835 boiling Methods 0.000 description 10
- 238000009413 insulation Methods 0.000 description 10
- 238000010792 warming Methods 0.000 description 10
- HXWWMGJBPGRWRS-CMDGGOBGSA-N 4- -2-tert-butyl-6- -4h-pyran Chemical compound O1C(C(C)(C)C)=CC(=C(C#N)C#N)C=C1\C=C\C1=CC(C(CCN2CCC3(C)C)(C)C)=C2C3=C1 HXWWMGJBPGRWRS-CMDGGOBGSA-N 0.000 description 8
- 229940125810 compound 20 Drugs 0.000 description 8
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 5
- CZRDZAGTSCUWNG-UHFFFAOYSA-M chloro(dimethyl)tin Chemical compound C[Sn](C)Cl CZRDZAGTSCUWNG-UHFFFAOYSA-M 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 230000003111 delayed effect Effects 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical group [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 5
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 230000003068 static effect Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- OMBVEVHRIQULKW-DNQXCXABSA-M (3r,5r)-7-[3-(4-fluorophenyl)-8-oxo-7-phenyl-1-propan-2-yl-5,6-dihydro-4h-pyrrolo[2,3-c]azepin-2-yl]-3,5-dihydroxyheptanoate Chemical compound O=C1C=2N(C(C)C)C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C=3C=CC(F)=CC=3)C=2CCCN1C1=CC=CC=C1 OMBVEVHRIQULKW-DNQXCXABSA-M 0.000 description 4
- LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 description 4
- ISMDILRWKSYCOD-GNKBHMEESA-N C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O Chemical compound C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O ISMDILRWKSYCOD-GNKBHMEESA-N 0.000 description 4
- 229940126639 Compound 33 Drugs 0.000 description 4
- 229940125773 compound 10 Drugs 0.000 description 4
- 229940126540 compound 41 Drugs 0.000 description 4
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 3
- 229940125833 compound 23 Drugs 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical group C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 3
- 239000007772 electrode material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 description 1
- IRBAWVGZNJIROV-SFHVURJKSA-N 9-(2-cyclopropylethynyl)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CC4CC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 IRBAWVGZNJIROV-SFHVURJKSA-N 0.000 description 1
- 238000004057 DFT-B3LYP calculation Methods 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000002484 cyclic voltammetry Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011982 device technology Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- BJXYHBKEQFQVES-NWDGAFQWSA-N enpatoran Chemical compound N[C@H]1CN(C[C@H](C1)C(F)(F)F)C1=C2C=CC=NC2=C(C=C1)C#N BJXYHBKEQFQVES-NWDGAFQWSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
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- 239000011521 glass Substances 0.000 description 1
- 230000003760 hair shine Effects 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- ARRNBPCNZJXHRJ-UHFFFAOYSA-M hydron;tetrabutylazanium;phosphate Chemical compound OP(O)([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC ARRNBPCNZJXHRJ-UHFFFAOYSA-M 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
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- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
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- 230000000171 quenching effect Effects 0.000 description 1
- 238000005395 radioluminescence Methods 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- 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
- 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
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- 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
- 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
-
- 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 discloses a kind of boracic organic derivative and its application in organic electroluminescence device, the compound is using five-membered ring fused benzene as core, on the centrally located five-membered ring of boron element；The compound has the characteristics that intermolecular be not easy to crystallize, be not easy to assemble, have good filming.The compounds of this invention as organic electroluminescence device emitting layer material in use, device current efficiency, power efficiency and external quantum efficiency are greatly improved；Meanwhile device lifetime is promoted clearly.
Description
Technical field
The present invention relates to technical field of semiconductors, more particularly, to a kind of boracic organic compound, as well as shine
Application of the layer material on Organic Light Emitting Diode.
Background technique
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology can both be used to make
New display product is made, production novel illumination product is can be used for, is expected to substitute existing liquid crystal display and fluorescent lighting,
Application prospect is very extensive.
Structure of the OLED luminescent device like sandwich, including electrode material film layer, and be clipped in Different electrodes film layer it
Between organic functional material, various different function materials are overlapped mutually depending on the application collectively constitutes OLED luminescent device together.
As current device, when the two end electrodes application voltage to OLED luminescent device, and pass through electric field action organic layer functional material
Positive and negative charge in film layer, positive and negative charge is further compound in luminescent layer, i.e. generation OLED electroluminescent.
Application of the Organic Light Emitting Diode (OLEDs) in terms of large-area flat-plate is shown and is illuminated causes industry and
The extensive concern of art circle.However, traditional organic fluorescence materials can only be shone using 25% singlet exciton to be formed is electrically excited, device
The internal quantum efficiency of part is lower (up to 25%).External quantum efficiency is generally lower than 5%, and there are also very big with the efficiency of phosphorescent devices
Gap.Although phosphor material can efficiently use electricity since the strong SO coupling in heavy atom center enhances intersystem crossing
The singlet exciton formed and Triplet exciton are excited, makes the internal quantum efficiency of device up to 100%.But phosphor material exists
Expensive, stability of material is poor, and device efficiency tumbles the problems such as serious and limits it in the application of OLEDs.
Hot activation delayed fluorescence (TADF) material is the third developed after organic fluorescence materials and organic phosphorescent material
For luminous organic material.Such material generally has that small singlet-triplet is poor (△ EST), and triplet excitons can be with
It is transformed into singlet exciton by anti-intersystem crossing to shine.This can make full use of the singlet exciton for being electrically excited lower formation and three
Line state exciton, the internal quantum efficiency of device can achieve 100%.Meanwhile material structure is controllable, property is stablized, cheap nothing
Precious metal is needed, in having a extensive future for the field OLEDs.
Although theoretically 100% exciton utilization rate may be implemented in TADF material, following problem there are in fact: (1)
T1 the and S1 state for designing molecule has strong CT feature, very small S1-T1 state energy gap, although can realize by TADF process
High T1 → S1 state exciton conversion ratio, but low S1 state radiation transistion rate is also resulted in, consequently it is difficult to have both (or realizing simultaneously)
High exciton utilization rate and high fluorescent radiation efficiency；(2) even if having used doping device to mitigate T exciton concentration quenching effect, greatly
Efficiency roll-off is serious at higher current densities for the device of most TADF materials.
For current OLED shows the actual demand of Lighting Industry, the development of OLED material is also far from enough at present, falls
Afterwards in the requirement of panel manufacturing enterprise, the organic functional material as material enterprise development higher performance is particularly important.
Summary of the invention
In view of the above-mentioned problems existing in the prior art, this application provides a kind of boracic organic compound and its in Organic Electricity
Application in electroluminescence device.The compounds of this invention is based on TADF mechanism, is applied to organic electroluminescent as emitting layer material
Device, the device that the present invention makes have good photoelectric properties, can satisfy the requirement of panel manufacturing enterprise.
Technical scheme is as follows:
A kind of boracic organic compound, shown in the structure of the organic compound such as general formula (1):
The expression hydrogen atom or C of R1*-R5* independently1-6Alkyl, C2-6Unsaturated alkyl, naphthenic base, replace or
Unsubstituted C6-30Aromatic radical or heteroaryl；Wherein R2*-R5*-Ar-R or-R, Ar can also be independently expressed as
Indicate C6-20Arlydene；R2* with R3*、R3* with R4*、R4* with R5* it can mutually be bonded to form cyclic structure or not be bonded mutually
Form cyclic structure；
R6*-R9* expression hydrogen atom or substituent group independently, wherein R6* with R7*、R7* with R8*、R8* with R9* at least
One group of bond is at structure shown in general formula (2)；
B is selected fromX1It is expressed as oxygen atom, sulphur atom, selenium atom, C1-10The alkylidene of linear or branched alkyl group substitution,
One of the imido grpup that alkylidene, alkyl-substituted imido grpup or the aryl that aryl replaces replace；
R, R ' independently be expressed as structure shown in hydrogen atom or general formula (3), and R and R ' are not hydrogen atom simultaneously；
Wherein, R1、R2Structure shown in selection hydrogen atom or general formula (4) independently, and R1With R2Simultaneously it is not hydrogen:
Wherein, a is selected fromX1、X2、X3Independently be expressed as oxygen atom, sulphur atom, selenium atom,
C1-10What alkylidene, alkyl-substituted imido grpup or the aryl of alkylidene, aryl substitution that linear or branched alkyl group replaces replaced
One of imido grpup；
Structure shown in general formula (4) passes through CL1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL‘1-CL’2Key, CL‘2-CL’3Key or
CL‘3-CL’4Key is connect with structure shown in general formula (3).
The R2*-R5* at least one be expressed as-Ar-R or-R, Ar indicate C6-20Arlydene, R is expressed as general formula
(3) structure shown in；R6* with R7*、R7* with R8*、R8* with R9* at least one set of bond is at structure shown in general formula (2), formula of (2)
In R ' be expressed as hydrogen atom.
The R2* with R3*、R3* with R4*、R4* with R5* at least one set of mutually bond forms cyclic structure, R2*-R5* at least one
It is a be expressed as-Ar-R or-R, Ar indicate C6-20Arlydene, R is expressed as structure shown in general formula (3)；R6* with R7*、R7* with
R8*、R8* with R9* at least one set of bond at structure shown in general formula (2), the R ' in formula of (2) is expressed as hydrogen atom.
The R2* with R3*、R3* with R4*、R4* with R5* at least one set of mutually bond forms cyclic structure；R6* with R7*、R7*
With R8*、R8* with R9* at least one set of bond is at structure shown in general formula (2), and wherein R ' indicates structure shown in general formula (3), general formula (3)
In R1、R2Can independent expression hydrogen, methyl, isopropyl, tert-butyl, substitution or unsubstituted phenyl, substitution or do not take
Xenyl, substitution or the unsubstituted carbazyl in generation, substitution or unsubstituted dibenzofuran group, substitution or unsubstituted
9,9- dimethyl fluorenyl, substitution or unsubstituted acridinyl, substitution or unsubstituted diphenylacridine base, replace or
Unsubstituted phenoxazine base, substitution or unsubstituted phenothiazinyl.
Described R, R ' expression independently are as follows:
Any one of.
The concrete structure formula of the organic compound are as follows:
Any one of.
A kind of application of the boracic organic compound, the boracic organic compound are used to prepare organic electroluminescence
Part.
A kind of organic electroluminescence device containing the boracic organic compound, including luminescent layer, the luminescent layer packet
Include the boracic organic compound.
The organic electroluminescence device further includes substrate layer, anode layer, hole injection layer, hole transmission layer, electronics resistance
At least one layer of or multiple layer combination in barrier, hole blocking layer, electron transfer layer, electron injecting layer and cathode layer.
Above-mentioned hole injection layer can be HAT-CN, and with a thickness of 10nm, the material of hole transport can be NPB, and thickness can
Think 60nm；CBP is used as dopant material, the doping quality percentage in CBP as material of main part, the compounds of this invention
Than that can be 5%, thickness can be 40nm；The material of electron-transport can be TPBI, and thickness can be 40nm；The electronics note
The material for entering layer can be LiF, and thickness can be 1nm；Cathode reflection electrode layer can be aluminium.
The present invention is beneficial to be had the technical effect that
It include the group of electron donor (donor, D) and electron acceptor (acceptor, A) in the compounds of this invention structural molecule
Conjunction can increase Orbital Overlap, improve luminous efficiency, while connect what aromatic heterocycle group was spatially separating to obtain HOMO, LUMO
Charge transfer state material, boracic heterocyclic system has strong electron attraction, so that between electron donor connected to it
Frontier orbit overlapping is smaller, realizes the energy level difference of small S1 state and T1 state, to alter between realizing inverse system under the conditions of thermostimulation
More；The boron-containing compound since D-A forms certain dihedral angle, while connecting other aromatic structures, can destroy molecule
Crystallinity avoids intermolecular aggtegation, the film forming and fluorescence quantum efficiency having had, and is suitable as luminescent layer doping
Materials'use；
Compound of the present invention can be used as luminescent layer dopant material and make applied to OLED luminescent device, obtain good
Device performance, the current efficiency of device, power efficiency and external quantum efficiency are greatly improved；Meanwhile for the device longevity
Life is promoted clearly.Compound-material of the present invention has good application effect in OLED luminescent device, has good
Good industrialization prospect.
Detailed description of the invention
Fig. 1 is the device architecture schematic diagram of the compounds of this invention application；Wherein, 1 is transparent substrate layer, and 2 be ito anode
Layer, 3 be hole injection layer, and 4 be hole transmission layer, and 5 be luminescent layer, and 6 be electron transfer layer, and 7 be electron injecting layer, and 8 be cathode
Reflection electrode layer；
Fig. 2 is the effect of visualization figure of the HOMO energy level of compound 20；Fig. 3 is the visualization of the lumo energy of compound 20
Effect picture；Fig. 4 is the effect of visualization figure of the HOMO energy level of compound 50；Fig. 5 is the visualization of the lumo energy of compound 50
Effect picture；Fig. 6 is the effect of visualization figure of the HOMO energy level of compound 91；Fig. 7 is the visualization of the lumo energy of compound 91
Effect picture；Fig. 8 is the effect of visualization figure of the HOMO energy level of compound DCJTB；Fig. 9 is the lumo energy of compound DCJTB
Effect of visualization figure.
Specific embodiment
The synthesis of 1 compound 5 of embodiment
The synthesis step of compound is as follows:
A1 the and 50ml tetrahydrofuran of 0.01mol is added in 150ml four-hole boiling flask, leads to nitrogen protection, it is Celsius to be cooled to -78
Degree, is then slowly dropped into the n-BuLi cyclohexane solution of 0.02mol, after instillation, is stirred to react 3 hours, is warming up to -10
Degree Celsius, the tetrahydrofuran solution of 0.01mol dimethyltin chloride is instilled, after being added dropwise, insulation reaction 1 hour, then
It is warming up to room temperature, revolving removes tetrahydrofuran, then uses ethanol rinse 2 times, obtains faint yellow solid B1, and purity 98.2% is received
Rate 90%.HRMS (m/z): [M+H]+, theoretical value 417.14, measured value 417.11.
In 150ml there-necked flask, 50ml toluene is added, 0.01mol B1 leads to nitrogen protection, is cooled to -78 degrees Celsius, then
It is slowly dropped into the toluene solution containing 0.011mol C1, after being added dropwise, is stirred to react 4 hours, then warms naturally to room
Temperature, revolving remove toluene, then use ethanol rinse 2 times, cross silicagel column, obtain white solid D1.HRMS (m/z): [M+H]+, reason
It is 482.52 by value, measured value 482.44.
In 150ml there-necked flask, 0.01mol D1 and 50ml methylene chloride is added, is cooled to -15 degrees Celsius, then slowly divides
The NBS (N-bromosuccinimide) for criticizing addition 0.012mol warms naturally to room temperature after insulation reaction 3 hours.Then it is stirring
It mixes down, is slowly added to the distilled water of 50mol, 0.02mol sodium hydrogensulfite is then added, is stirred to react 30 minutes.Static liquid separation,
Water layer is removed, organic layer is removed water with anhydrous magnesium sulfate, and revolving removes solvent, and with ethanol rinse 2 times, is crossed silicagel column, is obtained white
Color solid E1.HRMS (m/z): [M+H]+, theoretical value 561.41, measured value 561.34.
0.01mol E1,0.011mol compound F1 is added under the atmosphere for being passed through nitrogen in the four-hole boiling flask of 150ml,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 50ml toluene, it is small to be heated to reflux 24
When, sampling contact plate, fully reacting, natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 98.3%,
Yield 70.5%.HRMS (m/z): [M+H]+, theoretical value 737.79, measured value 737.82.
The synthesis of 2 compound 10 of embodiment
The synthesis step of compound is as follows:
A2 the and 50ml tetrahydrofuran of 0.01mol is added in 150ml four-hole boiling flask, leads to nitrogen protection, it is Celsius to be cooled to -78
Degree, is then slowly dropped into the n-BuLi cyclohexane solution of 0.02mol, after instillation, is stirred to react 3 hours, is warming up to -10
Degree Celsius, the tetrahydrofuran solution of 0.01mol dimethyltin chloride is instilled, after being added dropwise, insulation reaction 1 hour, then
It is warming up to room temperature, revolving removes tetrahydrofuran, then uses ethanol rinse 2 times, obtains faint yellow solid B2, and purity 98.4% is received
Rate 89.5%.HRMS (m/z): [M+H]+, theoretical value 467.20, measured value 467.15.
In 150ml there-necked flask, 50ml toluene is added, 0.01mol B2 leads to nitrogen protection, is cooled to -78 degrees Celsius, then
It is slowly dropped into the toluene solution containing 0.011mol C1, after being added dropwise, is stirred to react 4 hours, then warms naturally to room
Temperature, revolving remove toluene, then use ethanol rinse 2 times, cross silicagel column, obtain white solid D2.HRMS (m/z): [M+H]+, reason
It is 532.58 by value, measured value 532.49.
In 150ml there-necked flask, 0.01mol D2 and 50ml methylene chloride is added, is cooled to -15 degrees Celsius, then slowly divides
The NBS (N-bromosuccinimide) for criticizing addition 0.012mol warms naturally to room temperature after insulation reaction 3 hours.Then it is stirring
It mixes down, is slowly added to the distilled water of 50mol, 0.02mol sodium hydrogensulfite is then added, is stirred to react 30 minutes.Static liquid separation,
Water layer is removed, organic layer is removed water with anhydrous magnesium sulfate, and revolving removes solvent, and with ethanol rinse 2 times, is crossed silicagel column, is obtained white
Color solid E2.HRMS (m/z): [M+H]+, theoretical value 596.44, measured value 596.35.
0.01mol E2,0.011mol compound F2 is added under the atmosphere for being passed through nitrogen in the four-hole boiling flask of 150ml,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 50ml toluene, it is small to be heated to reflux 24
When, sampling contact plate, fully reacting, natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 98.1%,
Yield 61.8%.HRMS (m/z): [M+H]+, theoretical value 787.85, measured value 787.79.
The synthesis of 3 compound 20 of embodiment
The synthesis step of compound is as follows:
A3 the and 50ml tetrahydrofuran of 0.01mol is added in 150ml four-hole boiling flask, leads to nitrogen protection, it is Celsius to be cooled to -78
Degree, is then slowly dropped into the n-BuLi cyclohexane solution of 0.02mol, after instillation, is stirred to react 3 hours, is warming up to -10
Degree Celsius, the tetrahydrofuran solution of 0.01mol dimethyltin chloride is instilled, after being added dropwise, insulation reaction 1 hour, then
It is warming up to room temperature, revolving removes tetrahydrofuran, then uses ethanol rinse 2 times, obtains faint yellow solid B3, and purity 97.6% is received
Rate 87.5%.HRMS (m/z): [M+H]+, theoretical value 391.06, measured value 391.12.
In 150ml there-necked flask, 50ml toluene is added, 0.01mol B3 leads to nitrogen protection, is cooled to -78 degrees Celsius, then
It is slowly dropped into the toluene solution containing 0.011mol C1, after being added dropwise, is stirred to react 4 hours, then warms naturally to room
Temperature, revolving remove toluene, then use ethanol rinse 2 times, cross silicagel column, obtain white solid D3.HRMS (m/z): [M+H]+, reason
It is 456.44 by value, measured value 456.38.
In 150ml there-necked flask, 0.01mol D3 and 50ml methylene chloride is added, is cooled to -15 degrees Celsius, then slowly divides
The NBS (N-bromosuccinimide) for criticizing addition 0.012mol warms naturally to room temperature after insulation reaction 3 hours.Then it is stirring
It mixes down, is slowly added to the distilled water of 50mol, 0.02mol sodium hydrogensulfite is then added, is stirred to react 30 minutes.Static liquid separation,
Water layer is removed, organic layer is removed water with anhydrous magnesium sulfate, and revolving removes solvent, and with ethanol rinse 2 times, is crossed silicagel column, is obtained white
Color solid E3.HRMS (m/z): [M+H]+, theoretical value 535.33, measured value 535.28.
0.01mol E3,0.011mol compound F3 is added under the atmosphere for being passed through nitrogen in the four-hole boiling flask of 150ml,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 50ml toluene, it is small to be heated to reflux 24
When, sampling contact plate, fully reacting, natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 98.4%,
Yield 61.8%.HRMS (m/z): [M+H]+, theoretical value 737.79, measured value 737.86.
The synthesis of 4 compound 23 of embodiment
The synthesis step of compound is as follows:
A4 the and 50ml tetrahydrofuran of 0.01mol is added in 150ml four-hole boiling flask, leads to nitrogen protection, it is Celsius to be cooled to -78
Degree, is then slowly dropped into the n-BuLi cyclohexane solution of 0.02mol, after instillation, is stirred to react 3 hours, is warming up to -10
Degree Celsius, the tetrahydrofuran solution of 0.01mol dimethyltin chloride is instilled, after being added dropwise, insulation reaction 1 hour, then
It is warming up to room temperature, revolving removes tetrahydrofuran, then uses ethanol rinse 2 times, obtains faint yellow solid B4, and purity 98.2% is received
Rate 86.8%.HRMS (m/z): [M+H]+, theoretical value 441.12, measured value 441.19.
In 150ml there-necked flask, 50ml toluene is added, 0.01mol B4 leads to nitrogen protection, is cooled to -78 degrees Celsius, then
It is slowly dropped into the toluene solution containing 0.011mol C1, after being added dropwise, is stirred to react 4 hours, then warms naturally to room
Temperature, revolving remove toluene, then use ethanol rinse 2 times, cross silicagel column, obtain white solid D4.HRMS (m/z): [M+H]+, reason
It is 506.50 by value, measured value 506.43.
In 150ml there-necked flask, 0.01mol D4 and 50ml methylene chloride is added, is cooled to -15 degrees Celsius, then slowly divides
The NBS (N-bromosuccinimide) for criticizing addition 0.012mol warms naturally to room temperature after insulation reaction 3 hours.Then it is stirring
It mixes down, is slowly added to the distilled water of 50mol, 0.02mol sodium hydrogensulfite is then added, is stirred to react 30 minutes.Static liquid separation,
Water layer is removed, organic layer is removed water with anhydrous magnesium sulfate, and revolving removes solvent, and with ethanol rinse 2 times, is crossed silicagel column, is obtained white
Color solid E4.HRMS (m/z): [M+H]+, theoretical value 585.39, measured value 585.34.
0.01mol E4,0.011mol compound F3 is added under the atmosphere for being passed through nitrogen in the four-hole boiling flask of 150ml,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 50ml toluene, it is small to be heated to reflux 24
When, sampling contact plate, fully reacting, natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 98.3%,
Yield 65.8%.HRMS (m/z): [M+H]+, theoretical value 787.85, measured value 787.76.
The synthesis of 5 compound 33 of embodiment
The synthesis step of compound is as follows:
0.01mol E4,0.011mol compound F4 is added under the atmosphere for being passed through nitrogen in the four-hole boiling flask of 150ml,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 50ml toluene, it is small to be heated to reflux 24
When, sampling contact plate, fully reacting, natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 98.5%,
Yield 63.8%.HRMS (m/z): [M+H]+, theoretical value 836.89, measured value 836.79.
The synthesis of 6 compound 41 of embodiment
The synthesis step of compound is as follows:
0.01mol E4,0.011mol compound F5 is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 150ml,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 50ml toluene, it is small to be heated to reflux 24
When, sampling contact plate, fully reacting, natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 98.1%,
Yield 66.2%.HRMS (m/z): [M+H]+, theoretical value 774.81, measured value 774.76.
The synthesis of 7 compound 50 of embodiment
The synthesis step of compound is as follows:
0.01mol E3,0.011mol compound F6 is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 150ml,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 50ml toluene, it is small to be heated to reflux 24
When, sampling contact plate, fully reacting, natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 98.5%,
Yield 66.7%.HRMS (m/z): [M+H]+, theoretical value 711.71, measured value 711.80.
The synthesis of 8 compound 54 of embodiment
The synthesis step of compound is as follows:
A5 the and 50ml tetrahydrofuran of 0.01mol is added in 150ml four-hole boiling flask, leads to nitrogen protection, it is Celsius to be cooled to -78
Degree, is then slowly dropped into the n-BuLi cyclohexane solution of 0.02mol, after instillation, is stirred to react 3 hours, is warming up to -10
Degree Celsius, the tetrahydrofuran solution of 0.01mol dimethyltin chloride is instilled, after being added dropwise, insulation reaction 1 hour, then
It is warming up to room temperature, revolving removes tetrahydrofuran, then uses ethanol rinse 2 times, obtains faint yellow solid B5, and purity 97.5% is received
Rate 88.1%.HRMS (m/z): [M+H]+, theoretical value 391.06, measured value 391.11.
In 150ml there-necked flask, 50ml toluene is added, 0.01mol B5 leads to nitrogen protection, is cooled to -78 degrees Celsius, then
It is slowly dropped into the toluene solution containing 0.011mol C1, after being added dropwise, is stirred to react 4 hours, then warms naturally to room
Temperature, revolving remove toluene, then use ethanol rinse 2 times, cross silicagel column, obtain white solid D5.HRMS (m/z): [M+H]+, reason
It is 456.44 by value, measured value 456.37.
In 150ml there-necked flask, 0.01mol D5 and 50ml methylene chloride is added, is cooled to -15 degrees Celsius, then slowly divides
The NBS (N-bromosuccinimide) for criticizing addition 0.012mol warms naturally to room temperature after insulation reaction 3 hours.Then it is stirring
It mixes down, is slowly added to the distilled water of 50mol, 0.02mol sodium hydrogensulfite is then added, is stirred to react 30 minutes.Static liquid separation,
Water layer is removed, organic layer is removed water with anhydrous magnesium sulfate, and revolving removes solvent, and with ethanol rinse 2 times, is crossed silicagel column, is obtained white
Color solid E5.HRMS (m/z): [M+H]+, theoretical value 535.33, measured value 535.41.
0.01mol E5,0.011mol compound F6 is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 150ml,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 50ml toluene, it is small to be heated to reflux 24
When, sampling contact plate, fully reacting, natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 98.1%,
Yield 59.7%.HRMS (m/z): [M+H]+, theoretical value 711.71, measured value 771.86.
The synthesis of 9 compound 73 of embodiment
The synthesis step of compound is as follows:
0.01mol E3,0.011mol compound F7 is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 150ml,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 50ml toluene, it is small to be heated to reflux 24
When, sampling contact plate, fully reacting, natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 98.6%,
Yield 64.8%.HRMS (m/z): [M+H]+, theoretical value 786.83, measured value 786.79.
The synthesis of 10 compound 91 of embodiment
The synthesis step of compound is as follows:
0.01mol E1,0.011mol compound F8 is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 150ml,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 50ml toluene, it is small to be heated to reflux 24
When, sampling contact plate, fully reacting, natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 98.3%,
Yield 67.2%.HRMS (m/z): [M+H]+, theoretical value 737.79, measured value 737.86.
The synthesis of 11 compound 107 of embodiment
The synthesis step of compound is as follows:
0.01mol E5,0.011mol compound F9 is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 150ml,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 50ml toluene, it is small to be heated to reflux 24
When, sampling contact plate, fully reacting, natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 98.2%,
Yield 66.8%.HRMS (m/z): [M+H]+, theoretical value 787.85, measured value 787.79.
The synthesis of 12 compound 122 of embodiment
The synthesis step of compound is as follows:
0.01mol E1,0.011mol compound F10 is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 150ml,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 50ml toluene, it is small to be heated to reflux 24
When, sampling contact plate, fully reacting, natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 98.5%,
Yield 67.4%.HRMS (m/z): [M+H]+, theoretical value 753.85, measured value 753.79
The synthesis of 13 compound 136 of embodiment
The synthesis step of compound is as follows:
0.01mol E4,0.011mol compound F11 is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 150ml,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 50ml toluene, it is small to be heated to reflux 24
When, sampling contact plate, fully reacting, natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 97.9%,
Yield 70.2%.HRMS (m/z): [M+H]+, theoretical value 803.85, measured value 803.76.
The synthesis of 14 compound 141 of embodiment
The synthesis step of compound is as follows:
0.01mol E1,0.011mol compound F12 is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 150ml,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 50ml toluene, it is small to be heated to reflux 24
When, sampling contact plate, fully reacting, natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 98.7%,
Yield 67.1%.HRMS (m/z): [M+H]+, theoretical value 787.85, measured value 787.82.
The synthesis of 15 compound 155 of embodiment
The synthesis step of compound is as follows:
0.01mol E5,0.011mol compound F13 is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 150ml,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 50ml toluene, it is small to be heated to reflux 24
When, sampling contact plate, fully reacting, natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 98.6%,
Yield 67.4%.HRMS (m/z): [M+H]+, theoretical value 786.83, measured value 786.76.
The synthesis of 16 compound 163 of embodiment
The synthesis step of compound is as follows:
0.01mol E5,0.011mol compound F14 is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 150ml,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 50ml toluene, it is small to be heated to reflux 24
When, sampling contact plate, fully reacting, natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 97.9%,
Yield 65.8%.HRMS (m/z): [M+H]+, theoretical value 711.71, measured value 711.68.
The compounds of this invention can be used as the use of luminescent layer dopant material, to the compounds of this invention 10, compound 20, chemical combination
Object 23, compound 33, compound 41, compound 50, compound 54 and current material DCJTB carry out hot property, fluorescence volume respectively
The measurement of sub- efficiency, singlet-triplet poor (△ Est), testing result are as shown in table 1.
Table 1
| Compound | Td(℃) | PLQY | △Est(eV) | HOMO(eV) | Cyclic voltammetric stability |
| Compound 10 | 402 | 81 | 0.10 | -5.72 | It is excellent |
| Compound 20 | 396 | 84 | 0.07 | -5.68 | It is excellent |
| Compound 23 | 397 | 80 | 0.12 | -5.66 | It is excellent |
| Compound 33 | 405 | 86 | 0.20 | -5.64 | It is excellent |
| Compound 41 | 408 | 74 | 0.15 | -5.74 | It is excellent |
| Compound 50 | 410 | 72 | 0.13 | -5.70 | It is excellent |
| Compound 54 | 407 | 68 | 0.27 | -5.77 | It is excellent |
| DCJTB | 385 | 81 | 0.58 | -5.70 | Generally |
Note: thermal weight loss temperature Td is the temperature of the weightlessness 1% in nitrogen atmosphere, in the TGA-50H heat of Japanese Shimadzu Corporation
It is measured on weight analysis instrument, nitrogen flow 20mL/min；λPLIt is sample solution fluorescence emission wavelengths, opens up Pu Kang using Japan
The measurement of SR-3 spectroradiometer；Φ f is that solid powder fluorescence quantum efficiency (utilizes the Maya2000Pro of U.S.'s marine optics
Fiber spectrometer, the test solid fluorescence amount of C-701 integrating sphere and marine optics LLS-LED the light source composition of Lan Fei company, the U.S.
Sub- efficiency test system, reference literature Adv.Mater.1997,9,230-232 method are measured)；Cyclic voltammetric stability
It is that the redox characteristic of material is observed by cyclic voltammetry to be identified；Test condition: test sample is dissolved in volume ratio
For the methylene chloride and acetonitrile mixed solvent of 2:1, concentration 1mg/mL, electrolyte is the tetrabutyl ammonium tetrafluoroborate or hexafluoro of 0.1M
The organic solution of phosphoric acid tetrabutylammonium.Reference electrode is Ag/Ag+ electrode, is titanium plate to electrode, working electrode is ITO electrode, is followed
Ring number is 20 times.
By upper table data it is found that the compounds of this invention thermal stability with higher, lesser singlet-triplet
Difference, higher Φ f, so that getting a promotion using the compounds of this invention as the OLED device efficiency of dopant material and service life.
CBP is steamed as material of main part, the compounds of this invention as doped luminescent material (doping mass concentration is 5%) altogether
It is fabricated to organic film.It is excited with the ultraviolet light of 365nm, measurement organic film fluorescence intensity is led to test angle distribution situation
It crosses optics fitting software and measures its anisotropy factor α.α is smaller, shows that the luminous subconstiuent of the level of organic film dopant material is got over
More, the utilization rate of dopant material radioluminescence is higher.As TADF material (thermal excitation delayed fluorescence material), the longevity of delayed fluorescence
Life is shorter, and triplet state is easy to return singlet by transition between anti-gap, is quenched so as to avoid triplet state, is able to ascend the effect of device
Rate and service life.The results are shown in Table 2.
Table 2
| Organic film (40nm) | α (degree) | Delayed fluorescence service life τ |
| CBP: compound 10 (5wt%) | 12.4 | 10.7 |
| CBP: compound 20 (5wt%) | 8.5 | 3.6 |
| CBP: compound 23 (5wt%) | 11.0 | 8.4 |
| CBP: compound 33 (5wt%) | 13.8 | 30.4 |
| CBP: compound 41 (5wt%) | 19.5 | 15.4 |
| CBP: compound 50 (5wt%) | 17.1 | 32.4 |
| CBP: compound 54 (5wt%) | 22.1 | 50.4 |
| CBP:DCJTB (5wt%) | 35 | Nothing |
Note: organic film carries out double source by ANS evaporated device and steams altogether, and vapor deposition substrate is high saturating quartz glass, and object is mixed
Impurity level concentration is 8%.After vapor deposition, (concentration of water and oxygen be less than 1ppm) is packaged in glove box.Sample is logical
Superrefraction rate matching fluid is placed in molten silicon semicolumn prism, changes light emitting angle by turntable, spectrum test uses
Sphere Optics SMS-500 type spectrometer.The delayed fluorescence service life is tested by the FLS980 transient lifetime of Edinburg instrument
Instrument obtains.
As can be seen from Table 2 relative to Traditional dopant material DCJTB, the sub- anisotropy factor that shines of the compounds of this invention
It is small, therefore the light extraction efficiency of organic layer can be improved, promote OLED device efficiency.Meanwhile triplet state can be efficiently used and swashed
The energy of son improves device efficiency.
Calculate by HOMO, lumo energy of the quantum-mechanical effects software ORCA to the compounds of this invention and go forward side by side
Row visualization, calculation method use B3LYP hydridization functional, base group 6-31g (d).HOMO effect of visualization such as Fig. 2 of compound 20
It is shown；The LUMO effect of visualization of compound 20 is as shown in Figure 3；The HOMO effect of visualization of compound 50 is as shown in figure 4, chemical combination
The LUMO effect of visualization of object 50 is as shown in Figure 5；The HOMO effect of visualization of compound 91 is as shown in fig. 6, compound 91
LUMO effect of visualization is as shown in Figure 7；The HOMO effect of visualization of compound DCJTB is as shown in figure 8, compound DCJTB
HOMO effect of visualization is as shown in Figure 9.
It can be seen greatly from the spatial distribution of HOMO, LUMO in the molecule, at the HOMO and lumo energy of the compounds of this invention
In the state that is spatially separating, HOMO, LUMO degree of overlapping are small, small so as to cause singlet-triplet difference, are conducive to triplet state and swash
Son is converted into singlet exciton by thermal excitation, theoretically device internal quantum efficiency can be made to reach 100%.
17-32 and comparative example 1 compound that the present invention will be described in detail synthesizes are in the devices as hair by the following examples
The application effect of photosphere dopant material.For embodiment 17-32 compared with comparative example 1, the manufacture craft of the device is identical, and
And identical baseplate material and electrode material are used, the film thickness of electrode material is also consistent, except that in device
Emitting layer material is changed, using the compounds of this invention.The structure composition of each embodiment obtained device such as 3 institute of table
Show.The performance test results of each device are as shown in table 4.
2/ hole injection layer of embodiment 17:ITO anode layer, 3 (HAT-CN, thickness 10nm)/hole transmission layer 4 (NPB, thickness
60nm)/luminescent layer 5 (the weight ratio blending of CBP and compound 18 according to 100:5, thickness 40nm)/electron transfer layer 6 (TPBI,
Thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode layer 8 (Al).The molecular structural formula of each compound is as follows:
Specific preparation process is as follows: transparent substrate layer 1 uses transparent material, such as glass；To ito anode layer 2, (film thickness is
It 150nm) is washed, i.e., carries out ultraviolet-ozone washing again after successively carrying out neutralizing treatment, pure water, drying to remove
The organic residue on the bright surface ITO.On having carried out the ito anode layer 2 after above-mentioned washing, using vacuum deposition apparatus, steam
The molybdenum trioxide HAT-CN that film thickness is 10nm is plated to use as hole injection layer 3.And then the NPB of 60nm thickness is deposited as empty
Cave transport layer 4.After above-mentioned hole mobile material vapor deposition, the luminescent layer 5 of OLED luminescent device is made, structure includes OLED
For the used material C BP of luminescent layer 5 as material of main part, compound 10 is used as dopant material, and dopant material doping ratio is 9% weight
Ratio is measured, luminescent layer film thickness is 40nm.After above-mentioned luminescent layer 5, continuation vacuum evaporation electron transport layer materials are TPBI, the material
The vacuum evaporation film thickness of material is 40nm, this layer is electron transfer layer 6.On electron transfer layer 6, pass through vacuum deposition apparatus, system
Make lithium fluoride (LiF) layer that film thickness is 1nm, this layer is electron injecting layer 7.On electron injecting layer 7, filled by vacuum evaporation
It sets, aluminium (Al) layer that production film thickness is 80nm, this layer is the use of cathode reflection electrode layer 8.OLED is completed as described above to shine
After device, anode and cathode is connected with well known driving circuit, the luminous efficiency of measurement device, luminescent spectrum and device
The I-E characteristic of part.
Table 3
Table 4
Note: for device detection performance using comparative example 1 as reference, 1 device performance indexes of comparative example is set as 1.0.Compare
The external quantum efficiency of example 1 is 3.0% (@3000cd/m2)；Driving service life (light emission luminance be original intensity 90%) is 200
Hour.Life-span test system is the OLED device life-span tester of owner of the invention and Shanghai University's joint development.
Compound of the present invention can shine as luminescent layer dopant material using with OLED from the results shown in Table 4
Element manufacturing, and compared with comparative example 1, either efficiency or service life obtain larger improvement than known OLED material, special
It is not the biggish promotion of efficiency acquisition of device.
Although disclosing the present invention by embodiment and preferred embodiment, it should be appreciated that it is public that the present invention is not limited to institutes
The embodiment opened.On the contrary, it will be understood by those skilled in the art that it is intended to various modifications and similar arrangement.Therefore, institute
Attached the scope of the claims should be consistent with widest explanation to cover all such modifications and similar arrangement.
Claims (9)
1. a kind of boracic organic compound, it is characterised in that shown in the structure of the organic compound such as general formula (1):
The expression hydrogen atom or C of R1*-R5* independently1-6Alkyl, C2-6Unsaturated alkyl, naphthenic base replace or do not take
The C in generation6-30Aromatic radical or heteroaryl；Wherein R2*-R5* can also independently be expressed as-Ar-R or-R, Ar indicate
C6-20Arlydene；R2* with R3*、R3* with R4*、R4* with R5* it can mutually be bonded to form cyclic structure or not mutually bond formation
Cyclic structure；
R6*-R9* expression hydrogen atom or substituent group independently, wherein R6* with R7*、R7* with R8*、R8* with R9* at least one set of
It is bonded into structure shown in general formula (2)；
B is selected fromX1It is expressed as oxygen atom, sulphur atom, selenium atom, C1-10Alkylidene, the aryl of linear or branched alkyl group substitution
One of the imido grpup that substituted alkylidene, alkyl-substituted imido grpup or aryl replaces；
R, R ' independently be expressed as structure shown in hydrogen atom or general formula (3), and R and R ' are not hydrogen atom simultaneously；
Wherein, R1、R2Structure shown in selection hydrogen atom or general formula (4) independently, and R1With R2Simultaneously it is not hydrogen:
Wherein, a is selected fromX1、X2、X3Independently be expressed as oxygen atom, sulphur atom, selenium atom, C1-10Straight chain
Or in the alkylidene of branched alkyl substitution, the alkylidene of aryl substitution, alkyl-substituted imido grpup or the imido grpup of aryl substitution
One kind；
Structure shown in general formula (4) passes through CL1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL‘1-CL’2Key, CL‘2-CL’3Key or CL‘3-CL’4
Key is connect with structure shown in general formula (3).
2. boracic organic compound according to claim 1, it is characterised in that the R2*-R5* at least one is indicated
C is indicated for-Ar-R or-R, Ar6-20Arlydene, R is expressed as structure shown in general formula (3)；R6* with R7*、R7* with R8*、R8*
With R9* at least one set of bond at structure shown in general formula (2), the R ' in formula of (2) is expressed as hydrogen atom.
3. boracic organic compound according to claim 1, it is characterised in that: R2* with R3*、R3* with R4*、R4* with R5* extremely
Few one group mutually bond forms cyclic structure, R2*-R5* at least one be expressed as-Ar-R or-R, Ar indicate C6-20Asia virtue
Base, R are expressed as structure shown in general formula (3)；R6* with R7*、R7* with R8*、R8* with R9* at least one set of bond is tied at shown in general formula (2)
Structure, the R ' in formula of (2) are expressed as hydrogen atom.
4. boracic organic compound according to claim 1, it is characterised in that the R2* with R3*、R3* with R4*、R4* with
R5* at least one set of mutually bond forms cyclic structure；R6* with R7*、R7* with R8*、R8* with R9* at least one set of bond is at general formula (2)
Shown structure, wherein R ' indicates structure shown in general formula (3), the R in general formula (3)1、R2It can independent expression hydrogen, methyl, isopropyl
Base, tert-butyl, substitution or unsubstituted phenyl, substitution or unsubstituted xenyl, substitution or unsubstituted carbazyl,
Substitution or unsubstituted dibenzofuran group, substitution or unsubstituted 9,9- dimethyl fluorenyl, substitution or unsubstituted
Acridinyl, substitution or unsubstituted diphenylacridine base, substitution or unsubstituted phenoxazine base, substitution or unsubstituted
Phenothiazinyl.
5. boracic organic compound according to claim 1, it is characterised in that described R, R ' expression independently are as follows:
Any one of.
6. boracic organic compound according to claim 1, it is characterised in that the concrete structure formula of the organic compound
Are as follows:
Any one of.
7. a kind of application of any one of claim 1~6 boracic organic compound, it is characterised in that the boracic organises
It closes object and is used to prepare organic electroluminescence device.
8. a kind of organic electroluminescence device containing any one of the claim 1~6 boracic organic compound, including shine
Layer, it is characterised in that the luminescent layer includes the boracic organic compound.
9. organic electroluminescence device according to claim 8, which is characterized in that the organic electroluminescence device also wraps
Include substrate layer, anode layer, hole injection layer, hole transmission layer, electronic barrier layer, hole blocking layer, electron transfer layer, electronics note
Enter at least one layer of or multiple layer combination in layer and cathode layer.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109575055A (en) * | 2017-09-29 | 2019-04-05 | 江苏三月光电科技有限公司 | A kind of boracic five member ring heterocyclic compound and its application in organic electroluminescence device |
| CN109575054A (en) * | 2017-09-29 | 2019-04-05 | 江苏三月光电科技有限公司 | A kind of boracic hexa-member heterocycle derivative and its application in organic electroluminescence device |
| CN110078755A (en) * | 2019-05-30 | 2019-08-02 | 武汉天马微电子有限公司 | Compound, display panel and display device |
| CN110256473A (en) * | 2019-06-28 | 2019-09-20 | 武汉天马微电子有限公司 | A kind of compound, organic photoelectric device and electronic equipment |
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2017
- 2017-09-29 CN CN201710907099.7A patent/CN109535189A/en not_active Withdrawn
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| CN109575055A (en) * | 2017-09-29 | 2019-04-05 | 江苏三月光电科技有限公司 | A kind of boracic five member ring heterocyclic compound and its application in organic electroluminescence device |
| CN109575054A (en) * | 2017-09-29 | 2019-04-05 | 江苏三月光电科技有限公司 | A kind of boracic hexa-member heterocycle derivative and its application in organic electroluminescence device |
| CN110078755A (en) * | 2019-05-30 | 2019-08-02 | 武汉天马微电子有限公司 | Compound, display panel and display device |
| CN110078755B (en) * | 2019-05-30 | 2022-01-11 | 武汉天马微电子有限公司 | Compound, display panel and display device |
| CN110256473A (en) * | 2019-06-28 | 2019-09-20 | 武汉天马微电子有限公司 | A kind of compound, organic photoelectric device and electronic equipment |
| CN110256473B (en) * | 2019-06-28 | 2022-03-11 | 武汉天马微电子有限公司 | Compound, organic photoelectric device and electronic equipment |
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Application publication date: 20190329 |