CN114685538A - Boron-nitrogen compound and organic light-emitting device prepared from same - Google Patents
Boron-nitrogen compound and organic light-emitting device prepared from same Download PDFInfo
- Publication number
- CN114685538A CN114685538A CN202011631413.1A CN202011631413A CN114685538A CN 114685538 A CN114685538 A CN 114685538A CN 202011631413 A CN202011631413 A CN 202011631413A CN 114685538 A CN114685538 A CN 114685538A
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- substituted
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- deuterated
- phenyl
- biphenylyl
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- TZHYBRCGYCPGBQ-UHFFFAOYSA-N [B].[N] Chemical compound [B].[N] TZHYBRCGYCPGBQ-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 229910017464 nitrogen compound Inorganic materials 0.000 title claims description 14
- -1 boron-nitrogen organic compound Chemical class 0.000 claims abstract description 171
- 239000000463 material Substances 0.000 claims abstract description 81
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 239000010410 layer Substances 0.000 claims description 72
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 229910052805 deuterium Inorganic materials 0.000 claims description 20
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical group [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 18
- 229910052722 tritium Inorganic materials 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000002346 layers by function Substances 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 229910052796 boron Inorganic materials 0.000 claims description 7
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 7
- 239000002019 doping agent Substances 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000005561 phenanthryl group Chemical group 0.000 claims description 7
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000006413 ring segment Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 4
- 150000001975 deuterium Chemical group 0.000 claims description 4
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 4
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000001570 methylene group Chemical class [H]C([H])([*:1])[*:2] 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 239000000203 mixture Chemical class 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- LKCYMRFUTJFFSP-UHFFFAOYSA-N 9-oxoxanthene-1-carbonitrile Chemical class C1=CC(C#N)=C2C(=O)C3=CC=CC=C3OC2=C1 LKCYMRFUTJFFSP-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical group C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical group C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims 3
- 229910052582 BN Inorganic materials 0.000 claims 2
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 claims 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- JEEHCWMEXMRCDS-UHFFFAOYSA-N bis(9H-fluoren-9-yl)methanone Chemical group C12=CC=CC=C2C2=CC=CC=C2C1C(=O)C1C2=CC=CC=C2C2=CC=CC=C21 JEEHCWMEXMRCDS-UHFFFAOYSA-N 0.000 claims 1
- 239000011737 fluorine Chemical group 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 6
- 230000009477 glass transition Effects 0.000 abstract description 4
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 abstract description 3
- 238000006862 quantum yield reaction Methods 0.000 abstract description 2
- 239000004065 semiconductor Substances 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 description 29
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 21
- 239000010408 film Substances 0.000 description 15
- 238000012360 testing method Methods 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 239000007772 electrode material Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 3
- DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-UHFFFAOYSA-N 0.000 description 3
- 229940127007 Compound 39 Drugs 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- QXOGPTXQGKQSJT-UHFFFAOYSA-N 1-amino-4-[4-(3,4-dimethylphenyl)sulfanylanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound Cc1ccc(Sc2ccc(Nc3cc(c(N)c4C(=O)c5ccccc5C(=O)c34)S(O)(=O)=O)cc2)cc1C QXOGPTXQGKQSJT-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- CDEASXIPDPAOGW-UHFFFAOYSA-N bis[4-(9,9-dimethylacridin-10-yl)phenyl]methanone Chemical compound C12=CC=CC=C2N(C2=C(C1(C)C)C=CC=C2)C1=CC=C(C(=O)C2=CC=C(N3C4=CC=CC=C4C(C4=C3C=CC=C4)(C)C)C=C2)C=C1 CDEASXIPDPAOGW-UHFFFAOYSA-N 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 108010043121 Green Fluorescent Proteins Proteins 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 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
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
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- 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
- C07F5/027—Organoboranes and organoborohydrides
-
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- 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
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/104—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with other heteroatoms
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Abstract
The invention relates to a boron-nitrogen organic compound and an organic electroluminescent device containing the same, belonging to the technical field of semiconductors, wherein the structure of the compound is shown as a general formula (1); the compound has narrow half-peak width, high fluorescence quantum yield, high glass transition temperature, high molecular thermal stability and appropriate HOMO and LUMO energy levels, and when the compound is used as a doping material in a luminescent layer material of an OLED luminescent device, the current efficiency and the external quantum efficiency of the device are remarkably improved, meanwhile, the luminescent color purity and the service life of the device are also greatly improved, and the boron-nitrogen material is used as a luminescent layer green light doping material to enable the device to have good photoelectric property.
Description
Technical Field
The invention relates to the technical field of semiconductors, in particular to a boron-nitrogen compound and an organic light-emitting device prepared from the same.
Background
The traditional fluorescent doping material is limited by the early technology, only 25% singlet excitons formed by electric excitation can emit light, the internal quantum efficiency of the device is low (the highest is 25%), the external quantum efficiency is generally lower than 5%, and the efficiency of the device is far from that of a phosphorescence device. The phosphorescence material enhances intersystem crossing due to strong spin-orbit coupling of heavy atom center, and can effectively utilize singlet excitons and triplet excitons formed by electric excitation to emit light, so that the internal quantum efficiency of the device reaches 100%. However, most phosphorescent materials are limited in application in OLEDs due to problems of high price, poor material stability, poor color purity, serious device efficiency roll-off and the like.
With the coming of the 5G era, higher requirements are put forward on color development standards, and besides high efficiency and stability, the luminescent material also needs narrower half-peak width to improve the luminescent color purity of the device. The fluorescent doped material can realize high fluorescence quantum and narrow half-peak width through molecular engineering, the blue fluorescent doped material has obtained a stepwise breakthrough, the half-peak width of the boron material can be reduced to below 30nm, for example, the boron material with narrower half-wave width (31nm) is disclosed in the publication CN107417715A as the blue fluorescent doped material, and the device performance of the blue fluorescent doped material is slightly lower than that of the classic blue TADF material 2 CZPN; the human eye is a more sensitive green light region, and research is mainly focused on phosphorescent doped materials, but the luminescence peak type of the phosphorescent doped materials is difficult to narrow by a simple method, so that the research on the high-efficiency green fluorescent doped materials with narrow half-peak width has important significance for meeting higher color development standards.
In addition, TADF sensitized fluorescence Technology (TSF) combines TADF material and fluorescent doping material, TADF material is used as exciton sensitization medium, triplet excitons formed by electric excitation are converted into singlet excitons, energy is transferred to the fluorescent doping material through long-range energy transfer of the singlet excitons, and the quantum efficiency in the device can reach 100% as well.
The boron compound with the resonance structure can easily realize narrow half-peak-width luminescence, and the material can be applied to the TADF sensitized fluorescence technology to realize the preparation of devices with high efficiency and narrow half-peak-width emission. As disclosed in CN 107507921B and CN 110492006a, a technique of combining a light-emitting layer in which a TADF material having a difference between the lowest singlet level and the lowest triplet level of 0.2eV or less is used as a host and a boron-containing material is used as a dopant; CN110492005A and CN 110492009a disclose a light-emitting layer combination scheme using exciplex as a host and boron-containing material as a dopant; can realize the efficiency which is comparable with phosphorescence and has relatively narrow half-peak width. Therefore, the TADF sensitized fluorescent technology based on the narrow half-peak width boron luminescent material is developed, and has unique advantages and strong potential in the aspect of displaying indexes facing BT.2020.
Disclosure of Invention
In view of the above problems in the prior art, the present applicant provides a boron-nitrogen compound and an organic light emitting device prepared therefrom. The organic compound has narrow half-peak width, high fluorescence quantum yield, high glass transition temperature, high molecular thermal stability and appropriate HOMO and LUMO energy levels, and can be used as a green light doping material of a light-emitting layer of an organic electroluminescent device, so that the light-emitting color purity and the service life of the device are improved.
The invention provides a specific technical scheme as follows:
a boron-nitrogen compound used as OLED doping material, the structure of the boron-nitrogen compound is shown as general formula (1):
in the general formula (1), Y1-Y20Each independently represents N or C-Ra；
RaEach occurrence is independently represented by hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, or a substituted or unsubstituted heteroaryl group containing O,N, S, B, P, F at least one heteroatom C1-C18With electron-withdrawing groups of, adjacent R on the same aromatic ringaCan be connected with each other to form a ring;
Y11and Y12When represented by CH, Y11And Y12By single bonds, oxygen atoms, sulfur atoms, N-RbSubstituted or unsubstituted alkylene, substituted or unsubstituted alkenylene, or a combination thereof;
Y16and Y17When represented by CH, Y16And Y17Through oxygen atoms, sulfur atoms, N-RbSubstituted or unsubstituted alkylene, substituted or unsubstituted alkenylene, or a combination thereof; and Y is11And Y12、Y16And Y17At least one connection;
Rbeach occurrence is independently represented by substituted or unsubstituted alkyl, substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C2～C30A heteroaryl group;
the dotted line represents a five-membered ring formed by single bond linkage or not, and at least one dotted line forms a five-membered ring by single bond linkage;
the "substituted or unsubstituted" substituents are optionally selected from deuterium, tritium, C1～C10Alkyl, deuterium or tritium substituted C1～C10One or more of alkyl, aryl with 6-30 ring atoms substituted by deuterium or tritium, heteroaryl with 5-30 ring atoms, and heteroaryl with 5-30 ring atoms substituted by deuterium or tritium;
the hetero atom in the heteroaryl is selected from one or more of oxygen, sulfur and nitrogen.
Preferably, the structure of the boron-nitrogen compound is represented by any one of general formula (2-1) to general formula (2-3):
in the general formula (2-1) to the general formula (2-3),X1、X2each independently represents a dimethyl-substituted methylene group, a fluorenyl-substituted methylene group, an oxygen atom, a sulfur atom or N-Rb；
RbIs represented by substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C2～C30One of heteroaryl;
the substituents of the "substituted or unsubstituted" groups described above are optionally selected from: deuterium, tritium, cyano, halogen, C1-20Alkyl radical, C2-20Alkenyl radical, C6-30Aryl radical, C2-30One or more of the heteroaryl groups of (a).
Preferably, the boron-nitrogen compound has a structure shown in a general formula (3-1) or a general formula (3-2):
Z1-Z16represented by nitrogen atom or C (R)c) Adjacent to RcMay be bonded to form a ring;
Rceach occurrence is independently represented by hydrogen atom, deuterium atom, tritium atom, halogen, cyano, C1-10Alkyl, substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C2-30One of the heteroaryl groups of (a);
the substituents of the "substituted or unsubstituted" groups described above are optionally selected from: deuterium atom, tritium atom, cyano group, halogen, C1-20Alkyl radical, C2-20Alkenyl radical, C6-30Aryl radical, C2-30One or more of the heteroaryl groups of (a);
the hetero atom in the heteroaryl is one or more selected from oxygen atom, sulfur atom and nitrogen atom.
In a preferred embodiment, the R groupaExpressed as hydrogen, deuterium, tritium, methyl, deuterated methyl, tritiomethyl, trifluoromethyl, ethyl, tert-butyl substituted ethyl, deuterated ethyl, tritioethyl, isopropyl, phenyl substituted isopropyl, deuterated isopropyl, tritiated isopropyl, tert-butyl, deuterated tert-butylTritiated tert-butyl, deuterated cyclopentyl, tritiated cyclopentyl, adamantyl, cyclohexane, phenoxy, phenylthio, phenyl, deuterated phenyl, tritiated phenyl, biphenylyl, deuterated biphenylyl, tritiated biphenylyl, deuterated terphenyl, tritiated terphenyl, naphthyl, anthracenyl, phenanthryl, pyridyl, quinolyl, furyl, thienyl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenylyl, ethyl-substituted biphenylyl, isopropyl-substituted biphenylyl, tert-butyl-substituted biphenylyl, deuterated methyl-substituted phenyl, Deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenylyl, deuterated ethyl-substituted biphenylyl, deuterated isopropyl-substituted biphenylyl, deuterated tert-butyl-substituted biphenylyl, tritimethyl-substituted phenyl, tritiethyl-substituted phenyl, tritiisopropyl-substituted phenyl, trititert-butyl-substituted phenyl, tritimethyl-substituted biphenylyl, tritiethyl-substituted biphenylyl, tritiisopropyl-substituted biphenylyl, trititert-butyl-substituted biphenylyl, fluorine-substituted pyridyl, cyano, xanthenone, cyano-substituted phenyl, cyano-substituted pyridyl, trifluoromethyl-substituted aryl, trifluoromethyl-substituted pyridyl, phenyl-substituted triazinyl, nitrogen-substituted terphenyl, Aryl-substituted carbonyl, pyrimidinyl, pyrazinyl, pyridazinyl, azabenzofuranyl, azadimethylfluorenyl, azadiphenylfluorenyl, dimethylanthronyl, benzophenone, azadiphenylketone, 9-fluorenone, anthraquinone, diphenylsulfone derivative, and diphenylboryl;
Rbrepresented by phenyl, deuterated phenyl, tritiated phenyl, biphenylyl, deuterated biphenylyl, tritiated biphenylyl, deuterated terphenylyl, tritiated terphenylyl, naphthyl, anthryl, phenanthryl, biphenyl, phenanthryl, and mixtures thereof,Pyridyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenylyl, ethyl-substituted biphenylyl, isopropyl-substituted biphenylyl, tert-butyl-substituted biphenylyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenylyl, deuterated ethyl-substituted biphenylyl, deuterated isopropyl-substituted biphenylyl, deuterated tert-butyl-substituted biphenylyl, tritiomethyl-substituted phenyl, tritiomethyl-substituted biphenylyl, or tritiomethyl-substituted biphenylyl.
RcRepresented by hydrogen, deuterium, tritium, methyl, deuterated methyl, tritiomethyl, trifluoromethyl, ethyl, tert-butyl substituted ethyl, deuterated ethyl, tritiylethyl, isopropyl, phenyl substituted isopropyl, deuterated isopropyl, tritisopropyl, tert-butyl, deuterated tert-butyl, tritiated tert-butyl, deuterated cyclopentyl, tritiated cyclopentyl, adamantyl, cyclohexane, phenoxy, phenylthio, phenyl, deuterated phenyl, tritiated phenyl, biphenyl, deuterobiphenyl, tritiated terphenyl, naphthyl, anthracenyl, phenanthryl, pyridyl, quinolyl, furyl, thienyl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirofluorenyl, methyl substituted phenyl, tritiated cyclopentyl, tritiated cyclopentyl, adamantyl, cyclohexyl, phenoxy, phenylthio, phenyl, tritiated phenyl, terphenyl, naphthyl, anthryl, carbazolyl, and the like, Ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenylyl, ethyl-substituted biphenylyl, isopropyl-substituted biphenylyl, tert-butyl-substituted biphenylyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenylyl, deuterated ethyl-substituted biphenylyl, deuterated isopropyl-substituted biphenylyl, deuterated tert-butyl-substituted biphenylyl, deuterated methyl-substituted biphenylyl, deuterated ethyl-substituted biphenylyl, deuterated isopropyl-substituted biphenylyl, deuterated tert-butyl-substituted biphenylyl, deuterated isopropyl-substituted biphenylyl, and mixtures thereofButyl-substituted biphenylyl, tritiomethyl-substituted phenyl, tritioethyl-substituted phenyl, tritioisopropyl-substituted phenyl, tritiert-butyl-substituted phenyl, tritiomethyl-substituted biphenylyl, tritioethyl-substituted biphenylyl, tritioisopropyl-substituted biphenylyl, or tritiert-butyl-substituted biphenylyl.
Preferably, the specific structure of the boron-nitrogen compound is any one of the following structures:
an organic light-emitting device comprises a cathode, an anode and a functional layer, wherein the functional layer is positioned between the cathode and the anode, and the functional layer of the organic light-emitting device comprises the boron-nitrogen compound.
Preferably, the functional layer comprises a light emitting layer, and the doping material of the light emitting layer is the boron-nitrogen compound.
Preferably, the light-emitting layer includes a first host material, a second host material and a dopant material, at least one of the first host material and the second host material is a TADF material, and the dopant material is the boron-nitrogen compound.
Compared with the prior art, the invention has the beneficial technical effects that:
(1) the compound is applied to OLED devices, can be used as a green light doping material of a light-emitting layer material, can emit green fluorescence under the action of an electric field, and can be applied to the field of OLED illumination or OLED display;
(2) the compound has higher fluorescence quantum efficiency as a doping material, and the fluorescence quantum efficiency of the material is close to 100%;
(3) the compound is used as a doping material, and a TADF sensitizer is introduced as a second main body, so that the efficiency of the device can be effectively improved;
(4) the compound has a narrow spectrum FWHM, and can effectively improve the color gamut of a device and improve the luminous efficiency of the device;
(5) the compound has higher vapor deposition decomposition temperature, can inhibit vapor deposition decomposition of materials, and effectively prolongs the service life of devices.
Drawings
FIG. 1 is a schematic structural diagram of an OLED device using the materials listed in the present invention;
the organic electroluminescent device comprises a substrate layer 1, a transparent substrate layer 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9 and a cathode layer 10.
Detailed Description
The present invention will be described in detail with reference to the accompanying drawings and examples.
The technical solutions in the embodiments of the present invention are clearly and completely described below, and all other embodiments obtained by a person of ordinary skill in the art based on the embodiments of the present invention without creative efforts belong to the protection scope of the present invention.
The starting materials mentioned in the synthesis examples of the present invention are commercially available. For example, the reagent is available from Zhongjieyu Wangrun Co., Ltd, Kangyao Chemicals Co., Ltd, and Tokyo chemical industry Co., Ltd.
To perform structural analysis on the compounds prepared in the examples, the molecular weight was measured using MS.
Example 1: synthesis of Compound 1:
adding 0.012mol of raw material A1, 0.01mol of raw material B1 and 150ml of toluene into a three-neck flask under the protection of nitrogen, stirring and mixing, and then adding 5 multiplied by 10-5mol Pd2(dba)3，5×10-5mol P(t-Bu)30.03mol of sodium tert-butoxide is heated to 110 ℃ and reacted for 24 hours under reflux; naturally cooling to room temperature, filtering, carrying out reduced pressure rotary evaporation on the filtrate, and passing through a neutral silica gel column to obtain a target product intermediate M1; LC-MS: theoretical value of 559.21, found value of 560.26([ M + H ]]+)；
Adding 0.037mol of intermediate M1 into a three-neck flask at-30 ℃ in a three-neck flask under the protection of nitrogen, then adding 150ml of tert-butylbenzene, slowly dropwise adding 28.5ml of 1.6mol/L tert-butyllithium pentane solution, after dropwise adding, heating to 60 ℃, stirring for 1 hour, and distilling off components with the boiling point lower than tert-butyl benzene under reduced pressure; then the temperature is reduced to-30 ℃, 3.7ml of boron tribromide is slowly added, the temperature is raised to room temperature, and the stirring is continued for 0.5 hour. Cooling to 0 deg.c again, adding 10.6ml of N, N-diisopropyl ethylamine, stirring at room temperature until the heat generation is finished, and heating to 120 deg.c for further reaction for 2 hr. Cooling to room temperature, and sequentially separating with sodium acetate aqueous solution and ethyl acetate; passing through silica gel column (developing agent: heated chlorobenzene), cleaning, and precipitating to obtain compound 1; elemental analysis Structure (molecular formula C)40H28BN): theoretical value C, 90.06; h, 5.29; n, 2.63; test values are: c, 90.04; h, 5.28; and N, 2.65. LC-MS: theoretical value of 533.23, found value of 534.39([ M + H ]]+)。
The preparation methods of other objective compounds were similar to the preparation method of preparation example 1, and the specific structures of the starting materials and intermediates used in the present invention are shown in table 1. All raw materials or intermediates were purchased at midrange energy-saving million shares, inc.
TABLE 1
Example 11: synthesis of compound 39:
compound 39 was prepared as in example 1, except that a1 was replaced with E1 and starting material B1 was replaced with intermediate N1; elemental analysis Structure of Compound 39 (formula C)38H21BN2): theoretical value C, 88.38; h, 4.10; n, 5.42; test values are: c, 88.39; h, 4.10; and N, 5.40. LC-MS: theoretical value of 516.18, found value of 517.22([ M + H ]]+). LC-MS of intermediate G1: theoretical value of 542.15, found value of 543.19([ M + H ]]+)。
The synthesis steps of the intermediate N1 are as follows:
adding 0.05mol of raw material C1, 0.06mol of raw material D1 and 100ml of toluene in a three-mouth bottle under the protection of nitrogen, stirring and mixing, and then adding 0.0025mol of Pd (PPh)3)40.075mol of potassium carbonate, 50ml of mixed solution of water and ethanol in a ratio of 1:1, stirring and heating to 110 ℃, and carrying out reflux reaction for 24 hours; naturally cooling to room temperature, filtering, layering filtrate, taking an organic phase, carrying out reduced pressure rotary evaporation until no fraction is obtained, and passing through a neutral silica gel column to obtain an intermediate Q1; LC-MS: theoretical value of 464.15, found value of 465.41([ M + H ]]+)。
Adding 0.04mol of intermediate Q1, 0.05mol of triphenylphosphine and 100ml of o-dichlorobenzene into a three-neck bottle under the protection of nitrogen, stirring and mixing, heating to 180 ℃, and reacting for 12 hours; naturally cooling to room temperature, filtering, and decompressing the filtrateRotary evaporation to no fraction, passing through neutral silica gel column to obtain intermediate N1, LC-MS: theoretical value of 432.16, found value of 433.33([ M + H ]]+)。
Example 12: synthesis of compound 132:
compound 132 was prepared as in example 1, except a substitution of E1 for a1 and intermediate N2 for starting material B1; elemental analysis Structure of Compound 132 (formula C)36H21BN2): theoretical value C, 87.82; h, 4.30; n, 5.69; test values are: c, 87.84; h, 4.30; n, 5.67. LC-MS: theoretical value of 492.18, found value of 493.10([ M + H ]]+). LC-MS of intermediate G2: theoretical value of 518.15, found value of 519.19([ M + H ]]+)。
Intermediate N2 was prepared as in example 13, except that D1 was replaced with D2. LC-MS of intermediate Q2: theoretical value of 440.15, found value of 441.29([ M + H ]]+) (ii) a LC-MS of intermediate N2: theoretical value of 408.16, found value of 409.39([ M + H ]]+)。
Example 13: synthesis of compound 137:
compound 137 was prepared as in example 1, except that E1 was used instead of a1 and intermediate N3 was used instead of starting material B1; elemental analysis Structure of Compound 137 (formula C)40H28BN): theoretical value C, 90.06; h, 5.29; n, 2.63; test values are: c, 90.08; h, 5.27; and N, 2.63. LC-MS: theoretical value of 533.23, found value of 534.20([ M + H ]]+). LC-MS of intermediate G3: theoretical value of 559.21, found value of 560.34([ M + H ]]+)。
Intermediate N3 was prepared as in example 13, except that D1 was replaced with D3. LC-MS of intermediate Q3: theoretical value of 481.20, found value of 482.01([ M + H ]]+)；LC-MS of intermediate N3: theoretical value of 449.21, found value of 450.23([ M + H ]]+)。
Example 14: synthesis of compound 140:
compound 140 was prepared as in example 1, except a substitution of E1 for a1 and intermediate N4 for starting material B1; elemental analysis Structure of Compound 140 (formula C)46H32BN): theoretical value C, 90.64; h, 5.29; n, 2.30; test values are: c, 90.63; h, 5.27; and N, 2.32. LC-MS: theoretical value of 609.26, found value of 610.29([ M + H ]]+)。
LC-MS of intermediate G4: the theoretical value is found to be 636.34([ M + H ]]+)。
Intermediate N4 was prepared as in example 13, except that D1 was replaced with D4. LC-MS of intermediate Q4: theoretical value of 557.24, found value of 558.06([ M + H ]]+) (ii) a LC-MS of intermediate N4: theoretical value of 525.25, found value of 526.20([ M + H ]]+)。
Example 15: synthesis of compound 84:
compound 84 was prepared as in example 1, except intermediate E1 was used in place of A1 and the elemental analysis structure (formula C) of compound 84 was found49H28BNO): theoretical value C, 89.50; h, 4.29; n, 2.13; test values are: c, 89.53; h, 4.27; and N, 2.13. LC-MS: theoretical value of 657.23, found value of 658.11([ M + H ]]+). LC-MS of intermediate G5: theoretical value of 683.20, found value of 684.22([ M + H ]]+)。
Intermediate N5 was prepared as in example 13, except that D1 was replaced with D5. LC-MS of intermediate N5: theoretical value of 573.21, found value of 574.29([ M + H ]]+)。
ref-1 compound structureIs of the formula
And (4) obtaining the commercial purchase.
The structural formula of the ref-2 compound is
From the structure in published patent document CN109476682A, number compound 4. The preparation of ref-2 was carried out by reference to the synthetic method described in this patent.
The compound of the invention is used in a light-emitting device and can be used as a doping material of a light-emitting layer. The physicochemical properties of the compounds prepared in the above examples of the present invention were measured, and the results are shown in table 2:
TABLE 2
Note: the glass transition temperature Tg is determined by differential scanning calorimetry (DSC, DSC204F1 DSC, Germany Chi corporation), the heating rate is 10 ℃/min; the thermogravimetric loss temperature Td is a temperature at which 1% of the weight is lost in a nitrogen atmosphere, and is measured on a TGA-50H thermogravimetric analyzer of Shimadzu corporation, Japan, and the nitrogen flow rate is 20 mL/min; the highest occupied molecular orbital HOMO energy level is tested by an ionization energy testing system (IPS-3), and the test is a nitrogen environment; eg was measured by a two-beam uv-vis spectrophotometer (model: TU-1901), LUMO being HOMO + Eg; PLQY and FWHM were tested in the thin film state by the Fluorolog-3 series fluorescence spectrometer from Horiba.
As can be seen from the data in the above table, the compound of the present invention has higher glass transition temperature and decomposition temperature than the conventional green light-doped ref-1. The luminescent layer is used as a doping material of the luminescent layer, and can inhibit the crystallization and the film phase separation of the material; meanwhile, the decomposition of the material under high brightness can be inhibited, and the service life of the device is prolonged. In addition, the compound has a shallow HOMO energy level, is doped in a host material as a doping material, is favorable for inhibiting generation of carrier traps, and improves the energy transfer efficiency of a host and an object, so that the luminous efficiency of a device is improved.
Compared with the prior material ref-2, the compound has narrower half-peak width and higher PLQY.
The compound has higher fluorescence quantum efficiency as a doping material, and the fluorescence quantum efficiency of the material is close to 100%; meanwhile, the spectrum FWHM of the material is narrow, so that the color gamut of the device can be effectively improved, and the luminous efficiency of the device is improved; and finally, the evaporation decomposition temperature of the material is higher, so that the evaporation decomposition of the material can be inhibited, and the service life of the device is effectively prolonged.
The application effect of the synthesized OLED material of the present invention in the device is detailed by device examples 1-15 and device comparative examples 1-2. Compared with the device example 1, the device examples 2 to 15 and the device comparative examples 1 to 2 of the present invention have the same manufacturing process, and adopt the same substrate material and electrode material, and the film thickness of the electrode material is also kept consistent, except that the luminescent layer material in the device is replaced. The layer structures and test results of the device examples are shown in tables 3-1 and 4, respectively.
Device example 1
As shown in FIG. 1, the transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (having a film thickness of 150nm) is washed, i.e., washed with a cleaning agent (Semiclean M-L20), washed with pure water, dried, and then washed with ultraviolet rays and ozone to remove organic residues on the surface of the transparent ITO layer. On the ITO anode layer 2 after the above washing, HT-1 and HI-1 having a film thickness of 10nm were deposited as the hole injection layer 3 by a vacuum deposition apparatus, and the mass ratio of HT-1 to HI-1 was 97: 3. Then, HT-1 was evaporated to a thickness of 60nm as the hole transport layer 4. EB-1 was then evaporated to a thickness of 30nm as an electron blocking layer 5. After the evaporation of the electron blocking material is finished, a light emitting layer 6 of the OLED light emitting device is manufactured, CBP is used as a main material, a compound 1 is used as a doping material, the mass ratio of the CBP to the compound 1 is 97:3, and the thickness of the light emitting layer is 30 nm. After the light-emitting layer 6, HB-1 was continuously vacuum-deposited to a film thickness of 5nm, and this layer was a hole-blocking layer 7. After the hole-blocking layer 7, ET-1 and Liq were continuously vacuum-evaporated at a mass ratio of ET-1 to Liq of 1:1 and a film thickness of 30nm, and this layer was an electron-transporting layer 8. On the electron transport layer 8, a LiF layer having a film thickness of 1nm was formed by a vacuum evaporation apparatus, and this layer was an electron injection layer 9. On the electron injection layer 9, a vacuum deposition apparatus was used to produce an Mg: the Ag electrode layer is used as a cathode layer 10, and the mass ratio of Mg to Ag is 1: 9.
The effect of the synthesized OLED material of the present invention in the application of the device is detailed below by device examples 16-26 and device comparative example 3. Compared with the device example 1, the device examples 16 to 26 and the device comparative example 3 of the invention have the same manufacturing process, adopt the same substrate material and electrode material, and keep the film thickness of the electrode material consistent, except that the luminescent layer material in the device is replaced. The layer structures and test results of the device examples are shown in tables 3-2 and 4, respectively
Device example 16
The transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (film thickness of 150nm) is washed, that is, washed with a cleaning agent (SemicleanM-L20), washed with pure water, dried, and then washed with ultraviolet rays and ozone to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, HT-1 and HI-1 having a film thickness of 10nm were deposited as the hole injection layer 3 by a vacuum deposition apparatus, and the mass ratio of HT-1 to HI-1 was 97: 3. Then, HT-1 was evaporated to a thickness of 60nm as the hole transport layer 4. EB-1 was then evaporated to a thickness of 30nm as an electron blocking layer 5. After the evaporation of the electron blocking material is finished, a light emitting layer 6 of the OLED light emitting device is manufactured, and the structure of the light emitting layer 6 comprises CBP and DMAC-BP used by the OLED light emitting layer 6 as double main body materials, a compound 61 as a doping material, the mass ratio of the CBP to the DMAC-BP to the compound 61 is 67:30:3, and the thickness of the light emitting layer is 30 nm. After the light-emitting layer 6, HB-1 was continuously vacuum-deposited to a film thickness of 5nm, and this layer was a hole-blocking layer 7. After the hole-blocking layer 7, ET-1 and Liq were continuously vacuum-evaporated at a mass ratio of ET-1 to Liq of 1:1 and a film thickness of 30nm, and this layer was an electron-transporting layer 8. On the electron transport layer 8, a LiF layer having a film thickness of 1nm was formed by a vacuum evaporation apparatus, and this layer was an electron injection layer 9. On the electron injection layer 9, a vacuum deposition apparatus was used to produce an Mg: the Ag electrode layer is used as a cathode layer 10, and the mass ratio of Mg to Ag is 1: 9.
The molecular structural formula of the related material is shown as follows:
after the OLED light emitting device was completed as described above, the anode and cathode were connected by a known driving circuit, and the current efficiency, external quantum efficiency, and lifetime of the device were measured. Device examples and comparisons prepared in the same manner are shown in tables 3-1 and 3-2; the current efficiency, external quantum efficiency and lifetime test results of the obtained devices are shown in table 4.
TABLE 3-1
TABLE 3-2
TABLE 4
Note: voltage, current effectPeak of luminescence and ratio were measured using IVL (current-voltage-brightness) test system (frarda scientific instruments ltd, su); the life test system is an EAS-62C type OLED device life tester of Japan System research company; LT95 refers to the time it takes for the device luminance to decay to 95%; all data were at 10mA/cm2And (4) testing.
As can be seen from the device data results in table 4, compared with comparative device examples 1 to 3, the current efficiency, external quantum efficiency and device lifetime of the organic light emitting device of the present invention are greatly improved compared with the OLED device of the known material in both single-host system and dual-host system; when the TADF material is used as the second body, the efficiency of the device is obviously improved compared with that of a single body.
In summary, the present invention is only a preferred embodiment, and not intended to limit the present invention, and any modifications, equivalents, improvements, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (8)
1. The boron-nitrogen compound as an OLED doping material is characterized in that the structure of the boron-nitrogen compound is shown as a general formula (1):
in the general formula (1), Y1-Y20Each independently represents N or C-Ra；
RaEach occurrence is independently represented by hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, or C containing at least one heteroatom of O, N, S, B, P, F1-C18With electron-withdrawing groups of, adjacent R on the same aromatic ringaCan be connected with each other to form a ring;
Y11and Y12When represented by CH, Y11And Y12By single bonds, oxygen atoms, sulfur atoms, N-RbSubstituted or unsubstituted alkylene, substituted or unsubstituted alkenylene, or a combination thereof; y is16And Y17When represented by CH, Y16And Y17Through oxygen atoms, sulfur atoms, N-RbSubstituted or unsubstituted alkylene, substituted or unsubstituted alkenylene, or a combination thereof; and Y is11And Y12、Y16And Y17At least one connection;
Rbeach occurrence is independently represented by substituted or unsubstituted alkyl, substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C2～C30A heteroaryl group;
the dotted line represents a five-membered ring formed by single bond connection or no connection, and at least one dotted line forms a five-membered ring by single bond connection;
the "substituted or unsubstituted" substituents are optionally selected from deuterium, tritium, C1～C10Alkyl, deuterium or tritium substituted C1～C10One or more of alkyl, aryl with 6-30 ring atoms substituted by deuterium or tritium, heteroaryl with 5-30 ring atoms, and heteroaryl with 5-30 ring atoms substituted by deuterium or tritium;
the hetero atom in the heteroaryl is selected from one or more of oxygen, sulfur and nitrogen.
2. The boron-nitrogen-based compound according to claim 1, wherein the structure of the boron-nitrogen-based compound is represented by any one of general formula (2-1) to general formula (2-3):
in the general formulae (2-1) to (2-3), X1、X2Each independently represents a dimethyl-substituted methylene group, a fluorenyl-substituted methylene group, an oxygen atom, a sulfur atom or N-Rb；
RbIs represented by substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C2～C30One of heteroaryl;
the substituents of the "substituted or unsubstituted" groups described above are optionally selected from: deuterium, tritium, cyano, halogen, C1-20Alkyl radical, C2-20Alkenyl radical, C6-30Aryl radical, C2-30One or more of (b) heteroaryl.
3. The boron-nitrogen-based compound according to claim 2, wherein the structure of the boron-nitrogen-based compound is represented by a general formula (3-1) or a general formula (3-2):
Z1-Z16represented by nitrogen atom or C (R)c) Adjacent to RcMay be bonded to form a ring;
Rceach occurrence is independently represented by hydrogen atom, deuterium atom, tritium atom, halogen, cyano, C1-10Alkyl, substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C2-30One of the heteroaryl groups of (a);
the substituents of the "substituted or unsubstituted" groups described above are optionally selected from: deuterium atom, tritium atom, cyano group, halogen, C1-20Alkyl radical, C2-20Alkenyl radical, C6-30Aryl radical, C2-30One or more of the heteroaryl groups of (a);
the hetero atom in the heteroaryl is one or more selected from oxygen atom, sulfur atom and nitrogen atom.
4. The boron nitride compound according to any one of claims 1 to 3, wherein R isaExpressed as hydrogen, deuterium, tritium, methyl, deuterated methyl, tritiomethyl, trifluoromethyl, ethyl, tert-butyl substituted ethyl, deuterated ethyl, tritioethyl, isopropyl, phenyl substituted isopropyl, deuterated isopropylA group, a tritiated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a tritiated tert-butyl group, a deuterated cyclopentyl group, a tritiated cyclopentyl group, a cyclopentyl group, an adamantyl group, a cyclohexane group, a phenoxy group, a phenylthio group, a phenyl group, a deuterated phenyl group, a tritiated phenyl group, a biphenyl group, a deuterated biphenyl group, a tritiated biphenyl group, a deuterated terphenyl group, a tritiated terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyridyl group, a quinolyl group, a furyl group, a thienyl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9, 9-dimethylfluorenyl group, a 9, 9-diphenylfluorenyl group, a spirofluorenyl group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenyl group, an ethyl-substituted biphenyl group, an isopropyl-substituted biphenyl group, a tert-butyl-substituted biphenyl group, Deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenylyl, deuterated ethyl-substituted biphenylyl, deuterated isopropyl-substituted biphenylyl, deuterated tert-butyl-substituted biphenylyl, tritiomethyl-substituted phenyl, tritioethyl-substituted phenyl, tritioisopropyl-substituted phenyl, tritietero-butyl-substituted phenyl, tritiomethyl-substituted biphenylyl, tritioethyl-substituted biphenylyl, tritioisopropyl-substituted biphenylyl, tritietero-tert-butyl-substituted biphenylyl, fluorine atom-substituted pyridyl, cyano, xanthenone, cyano-substituted phenyl, cyano-substituted pyridyl, trifluoromethyl-substituted aryl, trifluoromethyl-substituted pyridyl, phenyl-substituted triazinyl, Nitrogen atom substituted terphenyl group, aryl group substituted carbonyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, azabenzofuranyl group, azabicyclofluorenyl group, azabiphenylfluorenyl group, dimethylanthrenyl group, benzophenone group, azabenzonyl group, 9-fluorenylketone group, anthraquinone group, diphenylsulfone group derivative, and diphenylboryl group;
Rbrepresented by phenyl, deuterated phenyl, tritiated phenyl, biphenyl, deuterated biphenyl, tritiated biphenyl, deuterated terphenyl, tritiated terphenylPhenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, pyridyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenylyl, ethyl-substituted biphenylyl, isopropyl-substituted biphenylyl, tert-butyl-substituted biphenylyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenylyl, deuterated ethyl-substituted biphenylyl, deuterated isopropyl-substituted biphenylyl, deuterated tert-butyl-substituted biphenylyl, tritimethyl-substituted phenyl, tritiethyl-substituted phenyl, tritiisopropyl-substituted phenyl, trititert-butyl-substituted phenyl, tritimethyl-substituted biphenylyl, tritiethyl-substituted biphenylyl, tritiisopropyl-substituted biphenylyl, or trititert-butyl-substituted biphenylyl.
RcRepresented by hydrogen, deuterium, tritium, methyl, deuterated methyl, tritiomethyl, trifluoromethyl, ethyl, tert-butyl substituted ethyl, deuterated ethyl, tritiylethyl, isopropyl, deuterated isopropyl, tritioisopropyl, phenyl substituted isopropyl, tert-butyl, deuterated tert-butyl, tritidotert-butyl, deuterated cyclopentyl, tritieterocyclopentyl, cyclopentyl, adamantyl, cyclohexane, phenoxy, phenylthio, phenyl, deuterated phenyl, tritiophenyl, biphenyl, deuterobiphenyl, tritidibiphenyl, trititerphenyl, deuteroterphenyl, trititerphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, pyridyl, quinolyl, furyl, thienyl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirofluorenyl, methyl substituted phenyl, tritiated cyclopentyl, tritiated cyclopentyl, adamantyl, phenyl, tritiated phenyl, terphenyl, biphenyl, carbazolyl, and carbazolyl, Ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenylyl, ethyl-substituted biphenylyl, isopropyl-substituted biphenylyl, tert-butyl-substituted biphenylyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenylyl, deuterated ethyl-substituted biphenylyl, and mixtures thereof,Deuterated isopropyl-substituted biphenylyl, deuterated tert-butyl-substituted biphenylyl, tritiomethyl-substituted phenyl, tritioethyl-substituted phenyl, tritiomethyl-substituted biphenylyl, tritioethyl-substituted biphenylyl, tritiomethyl-substituted biphenylyl, or tritiomethyl-substituted biphenylyl.
5. The boron-nitrogen-based compound according to claim 1, wherein the specific structure of the boron-nitrogen-based compound is any one of the following structures:
6. an organic light-emitting device comprising a cathode, an anode and a functional layer, the functional layer being located between the cathode and the anode, wherein the functional layer of the organic light-emitting device comprises the boron-nitrogen-based compound according to any one of claims 1 to 5.
7. The organic light-emitting device according to claim 7, wherein the functional layer comprises a light-emitting layer, and wherein the dopant material of the light-emitting layer is the boron-nitrogen-based compound according to any one of claims 1 to 5.
8. The organic light-emitting device according to claim 7, wherein the light-emitting layer comprises a first host material, a second host material and a dopant material, wherein at least one of the first host material and the second host material is a TADF material, and the dopant material is the boron nitride compound according to any one of claims 1 to 5.
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| US20160351811A1 (en) * | 2015-06-01 | 2016-12-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN107501311A (en) * | 2017-07-14 | 2017-12-22 | 瑞声科技（南京）有限公司 | Electroluminescent organic material and its luminescent device |
| US20200176680A1 (en) * | 2017-08-17 | 2020-06-04 | Kwansei Gakuin Educational Foundation | Organic electroluminescent element |
| CN111574544A (en) * | 2019-02-18 | 2020-08-25 | 江苏三月科技股份有限公司 | Organic compound containing boron and application thereof in organic electroluminescent device |
| CN112110949A (en) * | 2019-06-21 | 2020-12-22 | 学校法人关西学院 | Polycyclic aromatic compound, material for organic device, organic electroluminescent element, display device, and lighting device |
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| US20160351811A1 (en) * | 2015-06-01 | 2016-12-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN107501311A (en) * | 2017-07-14 | 2017-12-22 | 瑞声科技（南京）有限公司 | Electroluminescent organic material and its luminescent device |
| US20200176680A1 (en) * | 2017-08-17 | 2020-06-04 | Kwansei Gakuin Educational Foundation | Organic electroluminescent element |
| CN111574544A (en) * | 2019-02-18 | 2020-08-25 | 江苏三月科技股份有限公司 | Organic compound containing boron and application thereof in organic electroluminescent device |
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