CN107973795A - A kind of electroluminescent organic material, luminescent device and display - Google Patents
A kind of electroluminescent organic material, luminescent device and display Download PDFInfo
- Publication number
- CN107973795A CN107973795A CN201711182082.6A CN201711182082A CN107973795A CN 107973795 A CN107973795 A CN 107973795A CN 201711182082 A CN201711182082 A CN 201711182082A CN 107973795 A CN107973795 A CN 107973795A
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- CN
- China
- Prior art keywords
- substitution
- electroluminescence device
- organic electroluminescence
- fluorenyl
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000011368 organic material Substances 0.000 title claims abstract description 23
- 238000005401 electroluminescence Methods 0.000 claims abstract description 91
- 239000000463 material Substances 0.000 claims abstract description 65
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 15
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 4
- 238000006467 substitution reaction Methods 0.000 claims description 54
- -1 benzo anthryl Chemical group 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 16
- 125000001624 naphthyl group Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 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 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 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 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000005561 phenanthryl group Chemical group 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000000217 alkyl group Chemical class 0.000 claims description 4
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 4
- 125000003003 spiro group Chemical class 0.000 claims description 3
- 125000005605 benzo group Chemical group 0.000 claims 1
- 150000002220 fluorenes Chemical class 0.000 claims 1
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 230000027756 respiratory electron transport chain Effects 0.000 abstract description 28
- 238000005516 engineering process Methods 0.000 abstract description 4
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 96
- 238000001704 evaporation Methods 0.000 description 32
- 230000008020 evaporation Effects 0.000 description 32
- 238000007738 vacuum evaporation Methods 0.000 description 24
- 230000005540 biological transmission Effects 0.000 description 18
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 14
- 239000011521 glass Substances 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- 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 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000000975 dye Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 230000005611 electricity Effects 0.000 description 6
- CECAIMUJVYQLKA-UHFFFAOYSA-N iridium 1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 CECAIMUJVYQLKA-UHFFFAOYSA-N 0.000 description 6
- 239000012046 mixed solvent Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 5
- 150000001768 cations Chemical class 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- MEYZYGMYMLNUHJ-UHFFFAOYSA-N tunicamycin Natural products CC(C)CCCCCCCCCC=CC(=O)NC1C(O)C(O)C(CC(O)C2OC(C(O)C2O)N3C=CC(=O)NC3=O)OC1OC4OC(CO)C(O)C(O)C4NC(=O)C MEYZYGMYMLNUHJ-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000005311 nuclear magnetism Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000001044 red dye Substances 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 238000000926 separation method 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
- 125000005259 triarylamine group Chemical group 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- PVFOHMXILQEIHX-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-bromophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Br PVFOHMXILQEIHX-UHFFFAOYSA-N 0.000 description 1
- QPIAHSNQMIGOBB-UHFFFAOYSA-N CC(C)Oc1cc(N2C(c3ccccc3)=NC3c4cccnc4-c4ncccc4C23)ccc1-c(c(OC(C)C)c1)ccc1-[n]1c(-c2ccccc2)nc2c1c1cccnc1c1ncccc21 Chemical compound CC(C)Oc1cc(N2C(c3ccccc3)=NC3c4cccnc4-c4ncccc4C23)ccc1-c(c(OC(C)C)c1)ccc1-[n]1c(-c2ccccc2)nc2c1c1cccnc1c1ncccc21 QPIAHSNQMIGOBB-UHFFFAOYSA-N 0.000 description 1
- RDPYEZCQKRSCSA-UHFFFAOYSA-N CC(c(cc1)cc2c1C(C=CCC1)=C1C2(c1ccccc1)c1ccccc1)N(c(c1c2cccc1)c(cccc1)c1c2-[n]1c(C(CC2C3(c4ccccc4)c4ccccc4)=CC=C2C2C3=CC=CC2)nc2c(cccn3)c3c3ncccc3c12)c(c1c(c2c3cccn2)nccc1)c3N Chemical compound CC(c(cc1)cc2c1C(C=CCC1)=C1C2(c1ccccc1)c1ccccc1)N(c(c1c2cccc1)c(cccc1)c1c2-[n]1c(C(CC2C3(c4ccccc4)c4ccccc4)=CC=C2C2C3=CC=CC2)nc2c(cccn3)c3c3ncccc3c12)c(c1c(c2c3cccn2)nccc1)c3N RDPYEZCQKRSCSA-UHFFFAOYSA-N 0.000 description 1
- IUWIPCMIOFVRPV-NWRBIJAYSA-N CC1(C)c2cc(-c3nc(C(/C=C\C=N/Cc4c-5cccn4)I)c-5[n]3-c(c3c4CCCC3)c(C=CCC3)c3c4-[n]3c(-c4ccc5-c6ccccc6C(C)(C)c5c4)nc4c(cccn5)c5c5ncccc5c34)ccc2-c2c1cccc2 Chemical compound CC1(C)c2cc(-c3nc(C(/C=C\C=N/Cc4c-5cccn4)I)c-5[n]3-c(c3c4CCCC3)c(C=CCC3)c3c4-[n]3c(-c4ccc5-c6ccccc6C(C)(C)c5c4)nc4c(cccn5)c5c5ncccc5c34)ccc2-c2c1cccc2 IUWIPCMIOFVRPV-NWRBIJAYSA-N 0.000 description 1
- 0 CC1(C=CC=NC1c1ncccc1-1)c2c-1nc(C1C=C(C3(c(cccc4)c4C4=C3CCC=C4)C3=CCCC=C33)C3=CC1)[n]2C1c(cccc2)c2C(N2C(C3C(c4ncccc44)N=CCC3)=C4N[C@]2C(C*)=CC(C23c4ccccc4-c4ccccc24)=C(C)c2c3cccc2)=C2C=CC=CC12 Chemical compound CC1(C=CC=NC1c1ncccc1-1)c2c-1nc(C1C=C(C3(c(cccc4)c4C4=C3CCC=C4)C3=CCCC=C33)C3=CC1)[n]2C1c(cccc2)c2C(N2C(C3C(c4ncccc44)N=CCC3)=C4N[C@]2C(C*)=CC(C23c4ccccc4-c4ccccc24)=C(C)c2c3cccc2)=C2C=CC=CC12 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
- XXPBFNVKTVJZKF-UHFFFAOYSA-N dihydrophenanthrene Natural products C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000005909 ethyl alcohol group Chemical group 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- RHZWSUVWRRXEJF-UHFFFAOYSA-N indium tin Chemical compound [In].[Sn] RHZWSUVWRRXEJF-UHFFFAOYSA-N 0.000 description 1
- ZEWMZYKTKNUFEF-UHFFFAOYSA-N indium;oxozinc Chemical compound [In].[Zn]=O ZEWMZYKTKNUFEF-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 238000005036 potential barrier Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
-
- 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
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
-
- 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
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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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
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
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- Organic Chemistry (AREA)
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Abstract
The present invention relates to display technology field, more particularly to a kind of electroluminescent organic material, organic electroluminescence device and display.Shown in compound such as formula (1) according to the present invention：
Description
Technical field
The present invention relates to display technology field, more particularly to a kind of electroluminescent organic material, organic electroluminescence
Part and display.
Background technology
Organic electroluminescence device (Organic Light Emitting Display, abbreviation OLED) is put down as new
Panel display, is compared with liquid crystal display (Liquid Crystal Display, abbreviation LCD), has thin, light, wide viewing angle, master
It is dynamic shine, glow color is continuously adjustable, cost is low, fast response time, energy consumption is small, driving voltage is low, operating temperature range is wide, raw
Production. art is simple, luminous efficiency is high and can Flexible Displays the advantages that, obtained the very big concern of industrial circle and scientific circles.
The development of organic electroluminescence device promotes research of the people to electroluminescent organic material.Relative to inorganic hair
Luminescent material, electroluminescent organic material have the following advantages：Organic material processing performance is good, can pass through evaporation or the side of spin coating
Method forms a film on any substrate；The diversity of organic molecular structure allow to by Molecular Design and the method for modification come
Adjust the heat endurance of organic material, mechanical performance, shine and electric conductivity so that material is significantly improved space.
What the generation of organic electroluminescent was leaned on is the carrier (electronics and hole) transmitted in organic semiconducting materials
Restructuring.It is well known that the electric conductivity of organic material is very poor, there is no the energy band continued in organic semiconductor, the transmission of carrier is normal
Described with jump theory.In order to make organic electroluminescence device reach breakthrough in application aspect, it is necessary to overcome organic material
Electric charge injects and the difficulty of transmittability difference.Scientists pass through the adjustment of device architecture, such as increase device organic material layer
Number, and different organic layers is played the part of different device layers, such as the functional material having can promote electronics from cathode
Injection, some functional materials can promote hole to be injected from anode, and some materials can promote the transmission of electric charge, and some materials are then
It can play the role of stopping electronics or hole transport, the hair of most important a variety of colors certainly in organic electroluminescence device
Luminescent material will also achieve the purpose that to match with adjacent functional material, therefore, the organic electroluminescence device of excellent in efficiency long lifespan
Typically device architecture and various organic materials optimize arranging in pairs or groups as a result, this just designs and develops various structures for chemists
Functionalization material provides great opportunities and challenges.
Existing organic electroluminescence device generally comprises the cathode being arranged in order from top to bottom, electron injecting layer, electronics
Transport layer (Electron transport Layer, abbreviation ETL), organic luminous layer (EmittingLayer, abbreviation EML), sky
Cave transport layer, hole injection layer, anode and substrate.The raising of organic electroluminescence device efficiency, mainly in organic luminous layer
The interior formation probability for improving exciton as far as possible, therefore the organic luminous layer of organic electroluminescence device and electric transmission adjacent thereto
The material of layer plays the role of the luminous efficiency of organic electroluminescence device and brightness vital.And electricity of the prior art
The material or the material of main part of organic luminous layer that sub- transport layer is used make organic electroluminescence device have higher driving voltage
With relatively low luminous efficiency.
The content of the invention
The present invention provides a kind of electroluminescent organic material, the organic electroluminescence device comprising the compound and have
The display device of the organic electroluminescence device, to solve in the prior art the high driving voltage of organic electroluminescence device and
The problem of low luminous efficiency.
According to an aspect of the present invention, there is provided a kind of electroluminescent organic material, shown in the compound such as formula (1)：
Wherein, X, Y, Z are separately selected from：Carbon number is the aryl being made of carbon and hydrogen of 6-30, and m, n, q
1,2,3 are independently selected from, and m+n+q is more than 1；
G is selected from carbon number and forms aryl comprising carbon and hydrogen for 6-30, and carbon number is the aliphatic alkane base of 2-30.
Alternatively, X, Y, Z are separately selected from：Phenyl, naphthyl, anthryl, phenanthryl, dihydrophenanthrenyl, benzo anthryl, indeno
Fluorenyl, benzo fluorenyl, fluorenyl, it is Spirofluorene-based, substitution phenyl, substitution naphthyl, substitution anthryl, substitution phenanthryl, substitution
Dihydrophenanthrenyl, the benzo anthryl of substitution, the indeno fluorenyl of substitution, the benzo fluorenyl of substitution, the fluorenyl of substitution, the spiro fluorene of substitution
Base；G is selected from：Selected from methyl, ethyl, propyl group, butyl, amyl group, hexyl, cyclohexyl, phenyl, xenyl, naphthyl, fluorenyl, spiro fluorene
Base, alkyl-substituted phenyl, alkyl-substituted xenyl, alkyl-substituted naphthyl, alkyl-substituted fluorenyl, alkyl-substituted spiral shell
Fluorenyl, the phenyl of alkoxy substitution, the xenyl of alkoxy substitution, the naphthyl of alkoxy substitution, fluorenyl, the alkane of alkoxy substitution
Epoxide substitutes Spirofluorene-based.
Further, the substituted phenyl, the naphthyl of substitution, the anthryl of substitution, the phenanthryl of substitution, the dihydro phenanthrene of substitution
Base, substitution benzo anthryl, substitution indeno fluorenyl, substitution benzo fluorenyl, substitution fluorenyl, substitution it is Spirofluorene-based, it takes
Dai Ji is selected from：Methyl, ethyl, propyl group, butyl, amyl group, hexyl, cyclohexyl, methoxyl group, ethyoxyl, isopropoxy；The alkyl
It is substituted phenyl, alkyl-substituted xenyl, alkyl-substituted naphthyl, alkyl-substituted fluorenyl, alkyl-substituted Spirofluorene-based, its
Middle alkyl is selected from：Methyl, ethyl, propyl group, butyl, amyl group, hexyl, cyclohexyl；Phenyl, the alkoxy of the alkoxy substitution take
The xenyl in generation, the naphthyl of alkoxy substitution, the fluorenyl of alkoxy substitution, Spirofluorene-based, the wherein alkoxy choosing of alkoxy substitution
From methoxyl group, ethyoxyl, isopropoxy.
Alternatively, electroluminescent organic material according to the present invention is selected from：
According to another aspect of the present invention, there is provided a kind of organic electroluminescence device, the organic electroluminescence device
Electroluminescent organic material containing the present invention.
Alternatively, the material of main part of the organic luminous layer of the organic electroluminescence device or the material of electron transfer layer are
Electroluminescent organic material according to the present invention.
Alternatively, organic electroluminescence device according to the present invention, the color luminous layer is blue light-emitting layer, green hair
Photosphere or red light emitting layer.
According to another aspect of the present invention, there is provided a kind of display, the display device include organic according to the present invention
Electroluminescent device.
According to another aspect of the present invention, there is provided a kind of electronic equipment, the electronic equipment display include the present invention
The organic electroluminescence device；The electronic equipment includes TV, mobile phone, wrist-watch, e-book, motion bracelet, tablet electricity
Brain, the electronic entrance ticket with electronic display function, onboard instruments.
Beneficial effects of the present invention are as follows：
Compound provided by the invention is used in the electron transfer layer of organic electroluminescence device or the master of organic luminous layer
Body material, improves the luminous efficiency of organic electroluminescence device, reduces the driving voltage of organic electroluminescence device.
Embodiment
Embodiment is only the description of the invention, without forming the limitation to present invention, below in conjunction with
Specific embodiment is further described and describes to the present invention.
In order to which the compound of the present invention is explained in more detail, the synthetic method pair of above-mentioned particular compound will be enumerated below
The present invention is further described.
The synthesis of 1 compound P-1 of embodiment
It is as follows to synthesize equation：
The synthesis of intermediate 2- phenyl -1H- imidazos [4,5-f] [1,10] ferrosin is carried out first：
In 1000 milliliters of there-necked flasks, under nitrogen protection, 200 milliliters of absolute ethyl alcohols of addition, 200 milliliters of toluene, 21 grams
(0.1mol) 1,10- ferrosin -5,6- diamines, 10.6 grams of (0.1mol) benzaldehydes, 1 milliliter of glacial acetic acid, finishes and is to slowly warm up to
When back flow reaction 6 is small.Cooling, reaction solution is concentrated under reduced pressure into dry, and obtained solid is tied again with chloroform and alcohol mixed solvent
Crystalline substance, obtains 27.1 grams of 2- phenyl -1H- imidazos [4,5-f] [1,10] ferrosin, yield 91.55%.
Mass Spectrometer Method, m/e have been carried out to obtained intermediate 2- phenyl -1H- imidazos [4,5-f] [1,10] ferrosin：
296。
Nuclear-magnetism detection has been carried out to obtained intermediate 2- phenyl -1H- imidazos [4,5-f] [1,10] ferrosin, has been obtained
Nuclear magnetic spectrogram parsing data it is as follows：
1HNMR (500MHz, CDCl3)：δ 8.80 (d, 2H), δ 8.32 (m, 2H), δ 8.11 (m, 2H), δ 7.50 (m, 3H), δ
7.39 (m, 2H), δ 5.01 (s, 1H).
The synthesis of product P-1 is carried out again：
In 500 milliliters of there-necked flask, under nitrogen protection, add 150 milliliters of dry toluene, 6.51 grams
(0.022mol) 2- phenyl -1H- imidazos [4,5-f] [1,10] ferrosin, 2.36 grams of (0.01mol) Isosorbide-5-Nitrae-dibromobenzenes, 2.88
Gram (0.03mol) sodium tert-butoxide, 0.126 gram (0.00022mol) double (dibenzalacetone) palladiums, 0.44 gram (0.00022mol)
The toluene solution of 10% tri-butyl phosphine, be heated to back flow reaction 8 it is small when after be down to room temperature, add water, liquid separation, organic layer is used
Water washing after being dried with anhydrous magnesium sulfate, with silica gel post separation, uses petroleum ether to neutrality：Ethyl acetate：Dichloromethane (volume
Than for 2：3：5) eluted as eluant, eluent, obtain 5.3 grams of product shown in formula P-1, yield 80.30%.
To obtained compound P-1, Mass Spectrometer Method, product m/e are carried out：666.
Nuclear-magnetism detection, the parsing data of obtained nuclear magnetic spectrogram are as follows to obtained compound P-1 rows：
1HNMR (500MHz, CDCl3)：δ 8.81 (m, 4H), δ 8.26 (m, 4H), δ 8.15 (m, 4H), δ 7.60 (s, 4H), δ
7.50 (m, 6H), δ 7.39 (m, 4H).
The synthesis of 2 compound P-2 of embodiment~compound P-45
Benzaldehyde therein, is simply changed into the aldehyde of corresponding species by the synthesis of reference compound P-1 as needed, will wherein
Isosorbide-5-Nitrae-dibromobenzene change corresponding two bromo-derivative into, prepare compound P-2~P-45 totally 44 compounds, to obtained chemical combination
Thing has carried out Mass Spectrometer Method.
The mass spectrometric data of the species of aldehyde used, the species of two bromo-derivatives and gained compound see the table below in preparation process：
According to another aspect of the present invention, there is provided a kind of organic electroluminescence device, the organic electroluminescence device
The material of main part of organic luminous layer or the material of electron transfer layer are the compound according to the present invention.
The typical structure of organic electroluminescence device is：Substrate/anode/hole injection layer/hole transmission layer (HTL)/has
Machine luminescent layer (EL)/electron transfer layer (ETL)/electron injecting layer/cathode.Organic electroluminescence device structure can be single-shot light
Layer can also be multi-luminescent layer.
Wherein, substrate can use the substrate in conventional organic electroluminescence device, such as：Glass or plastics.Anode can be with
Using transparent high conductivity material, such as：Indium tin oxygen (ITO), indium zinc oxygen (IZO), stannic oxide (SnO2), zinc oxide (ZnO).
The hole-injecting material (Hole Injection Material, abbreviation HIM) of hole injection layer, it is desirable to which there is height
Heat endurance (high Tg), have a less potential barrier with anode, can vacuum evaporation form pin-hole free films.Common HTM is
Aromatic multi-amine class compound, mainly derivative of tri-arylamine group.
The hole mobile material (Hole Transport Material, abbreviation HTM) of hole transmission layer, it is desirable to which there is height
Heat endurance (high Tg), higher cavity transmission ability, can vacuum evaporation formed pin-hole free films.Common HTM is
Aromatic multi-amine class compound, mainly derivative of tri-arylamine group.
Organic luminous layer includes material of main part (host) and guest materials, and wherein guest materials is luminescent material, such as is contaminated
Material, material of main part need to have following characteristics：Reversible electrochemical redox current potential, with adjacent hole transmission layer and electronics
The HOMO energy levels and lumo energy that transport layer matches, good and the hole to match and electron transport ability, good is high
Heat endurance and film forming, and suitable singlet or triplet state energy gap are used for controlling exciton in luminescent layer, also with phase
Good energy transfer between the fluorescent dye or phosphorescent coloring answered.The luminescent material of organic luminous layer, by taking dyestuff as an example, it is necessary to
Possess following characteristics：With high fluorescence or phosphorescence quantum efficiency；The absorption spectrum of dyestuff and the emission spectrum of main body have
It is overlapping, i.e., main body is adapted to dyestuff energy, can effectively energy transmission from main body to dyestuff；The emission peak of red, green, blue to the greatest extent may be used
Can be narrow, with the excitation purity obtained；Stability is good, can be deposited etc..
The electron transport material (Electron transport Material, abbreviation ETM) of electron transfer layer requires ETM
There are reversible and sufficiently high electrochemical reduction current potential, suitable HOMO energy levels and LUMO (Lowest Unoccupied
Molecular Orbital, lowest unoccupied molecular orbital) energy level value enables electronics preferably to inject, and is preferably provided with
Hole blocking ability；Higher electron transport ability, the film forming having had and heat endurance.ETM is typically electron deficient knot
The aromatic compound of the conjugate planes of structure.Electron transfer layer uses Alq3 (8-hydroxyquinoline aluminium) or TAZ (3- phenyl -4-
(1 '-naphthyl) -5- benzene -1,2,4- triazoles) either TPBi (1,3,5- tri- (N- phenyl -2- benzimidazoles) benzene) or be derived from this three
Any two kinds of collocation of kind material.
According to another aspect of the present invention, there is provided a kind of display, the display include Organic Electricity according to the present invention
Electroluminescence device.
According to another aspect of the present invention, there is provided a kind of electronic equipment, the electronic equipment display include the present invention
The organic electroluminescence device；The electronic equipment includes TV, mobile phone, wrist-watch, e-book, motion bracelet, tablet electricity
Brain, the electronic entrance ticket with electronic display function.
It can be seen from the above that compound, organic electroluminescence device, display and the electricity with display device according to the present invention
The optional factor of sub- device is more, and claim according to the present invention can be combined into different embodiments.The implementation of the present invention
Example only as the specific descriptions to the present invention, is not intended as limitation of the present invention.Below in conjunction with the chemical combination containing the present invention
The present invention is described further as embodiment for the organic electroluminescence device of thing.
The different materials concrete structure used in the present invention is seen below：
Embodiment 3
Using the compound of the present invention as the electron transport material in organic electroluminescence device, 18 Organic Electricities are prepared altogether
Electroluminescence device, organic electroluminescence device as a comparison, electron transport material select Alq3.
Organic electroluminescence device structure is：ITO/HIL02(100nm)/NPB(40nm)/EM1(30nm)/ETL
(20nm)/LiF(0.5nm)/Al(150nm)。
Organic electroluminescence device preparation process is as follows：
The glass substrate for being coated with transparent conductive layer (as anode) is ultrasonically treated in cleaning agent, then
Rinse in deionized water, then the ultrasonic oil removing in acetone and alcohol mixed solvent, then be baked under clean environment and remove completely
Water, with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface, to improve the property on surface, improves and is noted with hole
Enter the binding ability of layer；
Above-mentioned glass substrate is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, the vacuum evaporation on anode
HIL02 is 100nm as hole injection layer, evaporation rate 0.1nm/s, evaporation thickness；
Vacuum evaporation NPB is as hole transmission layer, evaporation rate 0.1nm/s, evaporation thickness on hole injection layer
40nm；
Organic luminous layers of the vacuum evaporation EM1 as device on hole transmission layer, evaporation rate 0.1nm/s, steams
Plating total film thickness is 30nm；
Vacuum evaporation the compounds of this invention and Alq3 are distinguished on organic luminous layer as organic electroluminescence device
Electron transfer layer；Its evaporation rate is 0.1nm/s, and evaporation total film thickness is 20nm；
The LiF of vacuum evaporation 0.5nm is as electron injecting layer on electron transfer layer (ETL)；
The aluminium (Al) of vacuum evaporation 150nm is used as cathode on electron injecting layer.
Organic electroluminescence device performance is shown in Table 1：
Table 1
As can be seen that under identical brightness conditions, compound using the present invention has as made from electron transfer layer
Organic electroluminescence devices have relatively low drive compared with using Alq3 as organic electroluminescence device made from electron transfer layer
Dynamic voltage and higher current efficiency.
Embodiment 4
Using the compound of the present invention as the material of main part in red phosphorescent OLED organic electroluminescence devices, 14 are prepared altogether
A organic electroluminescence device.Organic electroluminescence device as a comparison, feux rouges material of main part select CBP.
Organic electroluminescence device structure is：ITO/NPB (20nm)/feux rouges material of main part (30nm)：Ir(piq)3
[5%]/TPBI (10nm)/Alq3 (15nm)/LiF (0.5nm)/Al (150nm).
Organic electroluminescence device preparation process is as follows：The glass plate for being coated with transparent conductive layer is cleaned in commercialization
It is ultrasonically treated in agent, rinses in deionized water, in acetone：Ultrasonic oil removing, is toasted under clean environment in alcohol mixed solvent
Moisture content is removed to complete, with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface；
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, above-mentioned
Vacuum evaporation hole transmission layer NPB on anode tunic, evaporation rate 0.1nm/s, evaporation thickness are 20nm；
Vacuum evaporation light emitting host material and dyestuff on hole transmission layer, as shining for organic electroluminescence device
Layer, evaporation rate 0.1nm/s, evaporation total film thickness is 30nm；Wherein " Ir (piq) 3 [5%] " refers to the doping ratio of red dye
The weight part ratio of example, i.e. feux rouges material of main part and Ir (piq) 3 are 100:5；
Vacuum evaporation electron transfer layer TPBI and Alq3, its evaporation rate are 0.1nm/s successively on luminescent layer, are steamed
It is respectively 10nm and 15nm to plate thickness；
The Al of the LiF of vacuum evaporation 0.5nm on the electron transport layer, 150nm are as electron injecting layer and cathode.
Organic electroluminescence device performance see the table below 2：
Table 2
By upper table it can be seen that, using chemical combination of the present invention as phosphorescence host organic electroluminescence device relative to use
CBP obtains preferable effect as the organic electroluminescence device of main body, obtains the current efficiency of higher and relatively low drive
Dynamic voltage.
Embodiment 5
Using the compound of the present invention as the material of main part in green phosphorescent OLED organic electroluminescence devices, 16 are prepared altogether
A organic electroluminescence device.Organic electroluminescence device as a comparison, green light material of main part select CBP.
Organic electroluminescence device structure is：ITO/NPB (20nm)/green light material of main part (30nm)：Ir(ppy)3
[7%]/TPBI (10nm)/Alq3 (15nm)/LiF (0.5nm)/Al (150nm).
Organic electroluminescence device preparation process is as follows：The glass plate for being coated with transparent conductive layer is cleaned in commercialization
It is ultrasonically treated in agent, rinses in deionized water, in acetone：Ultrasonic oil removing, is toasted under clean environment in alcohol mixed solvent
Moisture content is removed to complete, with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface；
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, above-mentioned
Vacuum evaporation hole transmission layer NPB on anode tunic, evaporation rate 0.1nm/s, evaporation thickness are 20nm；
Vacuum evaporation light emitting host material and dyestuff on hole transmission layer, as shining for organic electroluminescence device
Layer, evaporation rate 0.1nm/s, evaporation total film thickness is 30nm；Wherein " Ir (ppy) 3 [7%] " refers to the doping ratio of green light dyestuff
The weight part ratio of example, i.e. green light material of main part and Ir (ppy) 3 are 100:7；
Vacuum evaporation electron transfer layer TPBI and Alq3, its evaporation rate are 0.1nm/s successively on luminescent layer, are steamed
It is respectively 10nm and 15nm to plate thickness；
The Al of the LiF of vacuum evaporation 0.5nm on the electron transport layer, 150nm are as electron injecting layer and cathode.
Organic electroluminescence device performance is shown in Table 3：
Table 3
By upper table it can be seen that, using chemical combination of the present invention as phosphorescence host organic electroluminescence device relative to use
CBP obtains preferable effect as the organic electroluminescence device of main body, obtains the current efficiency of higher and relatively low drive
Dynamic voltage.
Embodiment 6
Passed using the compound of the present invention as the material of main part in red phosphorescent OLED organic electroluminescence devices and electronics
Defeated material, prepares 10 organic electroluminescence devices altogether.Organic electroluminescence device as a comparison, feux rouges material of main part are selected
CBP, electron transport material select TPBI/Alq3.
Organic electroluminescence device structure is：ITO/NPB (20nm)/feux rouges material of main part (30nm)：Ir(piq)3
[5%]/electron transport material (25nm)/LiF (0.5nm)/Al (150nm).
Organic electroluminescence device preparation process is as follows：The glass plate for being coated with transparent conductive layer is cleaned in commercialization
It is ultrasonically treated in agent, rinses in deionized water, in acetone：Ultrasonic oil removing, is toasted under clean environment in alcohol mixed solvent
Moisture content is removed to complete, with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface；
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, above-mentioned
Vacuum evaporation hole transmission layer NPB on anode tunic, evaporation rate 0.1nm/s, evaporation thickness are 20nm；
Vacuum evaporation light emitting host material and dyestuff on hole transmission layer, as shining for organic electroluminescence device
Layer, evaporation rate 0.1nm/s, evaporation total film thickness is 30nm；Wherein " Ir (piq) 3 [5%] " refers to the doping ratio of red dye
The weight part ratio of example, i.e. feux rouges material of main part and Ir (piq) 3 are 100:5；
The vacuum evaporation electron transfer layer successively on luminescent layer, for comparative device, electron transfer layer uses
TPBI and Alq3, its evaporation rate are 0.1nm/s, and evaporation thickness is respectively 10nm and 15nm；Come for the device of the present invention
Say, electron transfer layer selects the compounds of this invention, and evaporation thickness is 25nm；
The Al of the LiF of vacuum evaporation 0.5nm on the electron transport layer, 150nm are as electron injecting layer and cathode.
Organic electroluminescence device performance see the table below 4：
Table 4
By upper table it can be seen that：
At the same time using chemical combination of the present invention as the organic electroluminescence device of phosphorescence host and electron transfer layer relative to adopting
Preferable effect is obtained as the organic electroluminescence device of electron transfer layer by the use of CBP as main body, the compounds of this invention, is obtained
Obtained the current efficiency of higher and relatively low driving voltage.
At the same time using chemical combination of the present invention as the organic electroluminescence device of phosphorescence host and electron transfer layer relative to adopting
Obtained preferably as the organic electroluminescence device of electron transfer layer by the use of the compounds of this invention as main body, TPBI/Alq3
Effect, obtains the current efficiency of higher and relatively low driving voltage.
Embodiment 7
Passed using the compound of the present invention as the material of main part in green phosphorescent OLED organic electroluminescence devices and electronics
Defeated material, prepares 12 organic electroluminescence devices altogether.Organic electroluminescence device as a comparison, green light material of main part are selected
CBP, electron transport material select TPBI/Alq3.
Organic electroluminescence device structure is：ITO/NPB (20nm)/green light material of main part (30nm)：Ir(ppy)3
[7%]/electron transport material (25nm)/LiF (0.5nm)/Al (150nm).
Organic electroluminescence device preparation process is as follows：The glass plate for being coated with transparent conductive layer is cleaned in commercialization
It is ultrasonically treated in agent, rinses in deionized water, in acetone：Ultrasonic oil removing, is toasted under clean environment in alcohol mixed solvent
Moisture content is removed to complete, with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface；
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, above-mentioned
Vacuum evaporation hole transmission layer NPB on anode tunic, evaporation rate 0.1nm/s, evaporation thickness are 20nm；
Vacuum evaporation light emitting host material and dyestuff on hole transmission layer, as shining for organic electroluminescence device
Layer, evaporation rate 0.1nm/s, evaporation total film thickness is 30nm；Wherein " Ir (ppy) 3 [7%] " refers to the doping ratio of green light dyestuff
The weight part ratio of example, i.e. green light material of main part and Ir (ppy) 3 are 100:7；
The vacuum evaporation electron transfer layer successively on luminescent layer, for comparative device, electron transfer layer uses
TPBI and Alq3, its evaporation rate are 0.1nm/s, and evaporation thickness is respectively 10nm and 15nm；Come for the device of the present invention
Say, electron transfer layer selects the compounds of this invention, and evaporation thickness is 25nm；
The Al of the LiF of vacuum evaporation 0.5nm on the electron transport layer, 150nm are as electron injecting layer and cathode.
Organic electroluminescence device performance is shown in Table 5：
Table 5
By upper table it can be seen that：
At the same time using chemical combination of the present invention as the organic electroluminescence device of phosphorescence host and electron transfer layer relative to adopting
Preferable effect is obtained as the organic electroluminescence device of electron transfer layer by the use of CBP as main body, the compounds of this invention, is obtained
Obtained the current efficiency of higher and relatively low driving voltage.
At the same time using chemical combination of the present invention as the organic electroluminescence device of phosphorescence host and electron transfer layer relative to adopting
Obtained preferably as the organic electroluminescence device of electron transfer layer by the use of the compounds of this invention as main body, TPBI/Alq3
Effect, obtains the current efficiency of higher and relatively low driving voltage.
Obviously, various changes and modifications can be made to the invention without departing from essence of the invention by those skilled in the art
God and scope.In this way, if these modifications and changes of the present invention belongs to the scope of the claims in the present invention and its equivalent technologies
Within, then the present invention is also intended to comprising including these modification and variations.
Claims (9)
1. a kind of electroluminescent organic material, it is characterised in that shown in the compound such as formula (1)：
X, Y, Z are separately selected from：Carbon number is the aryl being made of carbon and hydrogen of 6-30, and m, n, q are independently
Be selected from 0,1,2,3, and m+n+q be more than 1；
G is selected from the aryl formed comprising carbon and hydrogen that carbon number is 6-30, and carbon number is the aliphatic alkane base of 2-30.
2. electroluminescent organic material according to claim 1, it is characterised in that X, Y, Z are separately selected from：Benzene
Base, naphthyl, anthryl, phenanthryl, dihydrophenanthrenyl, benzo anthryl, indeno fluorenyl, benzo fluorenyl, fluorenyl, it is Spirofluorene-based, substitution phenyl,
Substituted naphthyl, the anthryl of substitution, the phenanthryl of substitution, the dihydrophenanthrenyl of substitution, the benzo anthryl of substitution, the indenofluorene of substitution
Base, substitution benzo fluorenyl, substitution fluorenyl, substitution it is Spirofluorene-based；
G is selected from：Methyl, ethyl, propyl group, butyl, amyl group, hexyl, cyclohexyl, phenyl, xenyl, naphthyl, fluorenyl, it is Spirofluorene-based,
Alkyl-substituted phenyl, alkyl-substituted xenyl, alkyl-substituted naphthyl, alkyl-substituted fluorenyl, alkyl-substituted spiro fluorene
Base, the phenyl of alkoxy substitution, the xenyl of alkoxy substitution, the naphthyl of alkoxy substitution, fluorenyl, the alcoxyl of alkoxy substitution
Base substitutes Spirofluorene-based.
3. electroluminescent organic material according to claim 2, it is characterised in that：
The substituted phenyl, the naphthyl of substitution, the anthryl of substitution, the phenanthryl of substitution, the dihydrophenanthrenyl of substitution, the benzo of substitution
Anthryl, substitution indeno fluorenyl, substitution benzo fluorenyl, substitution fluorenyl, substitution it is Spirofluorene-based, its substituent is selected from：Methyl,
Ethyl, propyl group, butyl, amyl group, hexyl, cyclohexyl, methoxyl group, ethyoxyl, isopropoxy；
The alkyl-substituted phenyl, alkyl-substituted xenyl, alkyl-substituted naphthyl, alkyl-substituted fluorenyl, alkyl take
Generation it is Spirofluorene-based, wherein alkyl is selected from：Methyl, ethyl, propyl group, butyl, amyl group, hexyl, cyclohexyl；
Phenyl, the xenyl of alkoxy substitution, the naphthyl of alkoxy substitution, the fluorenes of alkoxy substitution of the alkoxy substitution
Base, alkoxy substitution it is Spirofluorene-based, wherein alkoxy be selected from methoxyl group, ethyoxyl, isopropoxy.
4. electroluminescent organic material according to claim 1, it is characterised in that the compound is selected from：
5. a kind of organic electroluminescence device, it is characterised in that it is any that the organic electroluminescence device contains claim 1-4
The electroluminescent organic material.
6. organic electroluminescence device according to claim 5, it is characterised in that the organic electroluminescence device has
The material of main part or electron transport material of machine luminescent layer are any electroluminescent organic materials of claim 1-4.
7. organic electroluminescence device according to claim 6, it is characterised in that the organic luminous layer is blue-light-emitting
Layer, green light emitting layer or red light emitting layer.
8. a kind of display, it is characterised in that including the organic electroluminescence device as described in claim 5-7 is any.
9. a kind of electronic equipment, the electronic equipment display includes the organic electroluminescent as described in claim 5-7 is any
Device；
The electronic equipment include TV, mobile phone, wrist-watch, e-book, motion bracelet, tablet computer, with electronic display function
Electronic entrance ticket, onboard instruments.
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| CN201711182082.6A CN107973795A (en) | 2017-11-23 | 2017-11-23 | A kind of electroluminescent organic material, luminescent device and display |
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| CN201711182082.6A CN107973795A (en) | 2017-11-23 | 2017-11-23 | A kind of electroluminescent organic material, luminescent device and display |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108129496A (en) * | 2017-12-01 | 2018-06-08 | 阜阳欣奕华材料科技有限公司 | A kind of compound, organic electroluminescence device and display device |
| CN108218867A (en) * | 2017-12-01 | 2018-06-29 | 阜阳欣奕华材料科技有限公司 | A kind of compound, organic electroluminescence device and display device |
| CN108218899A (en) * | 2017-12-01 | 2018-06-29 | 阜阳欣奕华材料科技有限公司 | A kind of compound, organic electroluminescence device and display device |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040234809A1 (en) * | 2003-05-20 | 2004-11-25 | Canon Kabushiki Kaisha | Oxazole-, thiazole-, and imidazole-fused phenanthroline molecules in organic light-emitting devices |
-
2017
- 2017-11-23 CN CN201711182082.6A patent/CN107973795A/en not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040234809A1 (en) * | 2003-05-20 | 2004-11-25 | Canon Kabushiki Kaisha | Oxazole-, thiazole-, and imidazole-fused phenanthroline molecules in organic light-emitting devices |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108129496A (en) * | 2017-12-01 | 2018-06-08 | 阜阳欣奕华材料科技有限公司 | A kind of compound, organic electroluminescence device and display device |
| CN108218867A (en) * | 2017-12-01 | 2018-06-29 | 阜阳欣奕华材料科技有限公司 | A kind of compound, organic electroluminescence device and display device |
| CN108218899A (en) * | 2017-12-01 | 2018-06-29 | 阜阳欣奕华材料科技有限公司 | A kind of compound, organic electroluminescence device and display device |
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