CN107698588A - Hot activation delayed fluorescence material and its organic electroluminescence device based on purine derivative - Google Patents
Hot activation delayed fluorescence material and its organic electroluminescence device based on purine derivative Download PDFInfo
- Publication number
- CN107698588A CN107698588A CN201710872085.6A CN201710872085A CN107698588A CN 107698588 A CN107698588 A CN 107698588A CN 201710872085 A CN201710872085 A CN 201710872085A CN 107698588 A CN107698588 A CN 107698588A
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- China
- Prior art keywords
- delayed fluorescence
- hot activation
- activation delayed
- fluorescence material
- purine derivative
- Prior art date
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- 239000000463 material Substances 0.000 title claims abstract description 63
- 230000004913 activation Effects 0.000 title claims abstract description 38
- 230000003111 delayed effect Effects 0.000 title claims abstract description 36
- 238000005401 electroluminescence Methods 0.000 title claims abstract description 22
- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title abstract 3
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 11
- 150000004982 aromatic amines Chemical class 0.000 claims abstract description 7
- 150000003212 purines Chemical class 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000002019 doping agent Substances 0.000 claims description 3
- 239000010410 layer Substances 0.000 claims 4
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims 2
- 239000002346 layers by function Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 17
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical class BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 16
- 238000005259 measurement Methods 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 10
- 239000000470 constituent Substances 0.000 description 10
- 238000001819 mass spectrum Methods 0.000 description 10
- 239000002994 raw material Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- -1 normal-butyl Chemical group 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 238000013519 translation Methods 0.000 description 5
- 230000014616 translation Effects 0.000 description 5
- 230000005540 biological transmission Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000004020 luminiscence type Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000027756 respiratory electron transport chain Effects 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- 0 O=C(c([n](c(-c1ccccc1)n1)-c2ccc(*(c3ccccc3)c3c(cccc4)c4ccc3)cc2)c1N=C1)N1c(cc1)ccc1N(c1ccccc1)c1c(CCC=C2)c2ccc1 Chemical compound O=C(c([n](c(-c1ccccc1)n1)-c2ccc(*(c3ccccc3)c3c(cccc4)c4ccc3)cc2)c1N=C1)N1c(cc1)ccc1N(c1ccccc1)c1c(CCC=C2)c2ccc1 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 235000011009 potassium phosphates Nutrition 0.000 description 2
- 239000010970 precious metal Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 1
- FTLFXJUEXREPLQ-UHFFFAOYSA-N CC[IH]Cc(cc1)ccc1N(c1ccc(C)cc1)c(cc1)ccc1-[n]1c(-c2ccccc2)nc(N=CN2c(cc3)ccc3N(c3ccc(C)cc3)c3ccc(C)cc3)c1C2=O Chemical compound CC[IH]Cc(cc1)ccc1N(c1ccc(C)cc1)c(cc1)ccc1-[n]1c(-c2ccccc2)nc(N=CN2c(cc3)ccc3N(c3ccc(C)cc3)c3ccc(C)cc3)c1C2=O FTLFXJUEXREPLQ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 206010054949 Metaplasia Diseases 0.000 description 1
- HRMPVZJRQJNDNI-UHFFFAOYSA-N O=C(c([n](c(-c1ccccc1)n1)-c(cc2)ccc2N2c3ccccc3N(c(cc3)ccc3-c(cccc3)c3-c3nc(N=CN(c(cc4)ccc4N4c5ccccc5[Si](c5ccccc5)(c5ccccc5)c5c4cccc5)C4=O)c4[n]3-c(cc3)ccc3N3c(cccc4)c4[Si](c4ccccc4)(c4ccccc4)c4c3cccc4)c3c2cccc3)c1N=C1)N1c(cc1)ccc1N1c2ccccc2N(c2ccccc2)c2c1cccc2 Chemical compound O=C(c([n](c(-c1ccccc1)n1)-c(cc2)ccc2N2c3ccccc3N(c(cc3)ccc3-c(cccc3)c3-c3nc(N=CN(c(cc4)ccc4N4c5ccccc5[Si](c5ccccc5)(c5ccccc5)c5c4cccc5)C4=O)c4[n]3-c(cc3)ccc3N3c(cccc4)c4[Si](c4ccccc4)(c4ccccc4)c4c3cccc4)c3c2cccc3)c1N=C1)N1c(cc1)ccc1N1c2ccccc2N(c2ccccc2)c2c1cccc2 HRMPVZJRQJNDNI-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 230000015689 metaplastic ossification Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/28—Oxygen atom
- C07D473/30—Oxygen atom attached in position 6, e.g. hypoxanthine
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
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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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
- C09K2211/1007—Non-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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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Abstract
The present invention provides a kind of hot activation delayed fluorescence material and its organic electroluminescence device based on purine derivative, belongs to technical field of organic electroluminescence.Hot activation delayed fluorescence material category is single in the prior art for solution, can not meet the technical problem of OLED demand.The present invention is using purine derivative as electron acceptor, using phenyl ring as connecting bridge, using arylamine or the hexa-atomic thick and heteroaromatic for containing nitrogen-atoms as electron donor, obtains a kind of hot activation delayed fluorescence material.The organic electroluminescence device prepared using hot activation delayed fluorescence material provided by the invention, external quantum efficiency is high, and maximum current efficiency is up to 18.63cd/A, maximum power efficiency is up to 11.30lm/W, with higher luminous efficiency, and driving voltage is low, is a kind of excellent OLED material.
Description
Technical field
The present invention relates to technical field of organic electroluminescence, and in particular to a kind of hot activation delay based on purine derivative
Fluorescent material and its organic electroluminescence device.
Background technology
Organic electroluminescent LED (Organic Light-Emitting Diode, OLED) refers to luminous organic material
The diode to be lighted in the presence of electric current or electric field, electric energy can be converted into luminous energy by it.Kodak Company in 1987
Tang etc. has invented sandwich type organic bilayer film luminescent device, this breakthrough, allows it is seen that OLED technology
Move towards practical, move towards the great potential of commercial market, started the research boom of Organic Light Emitting Diode.Over 30 years, OLED
Technology achieves development with rapid changepl. never-ending changes and improvements, is moved towards the industrialization production from laboratory research.All solid state, the active of OLED technology
Luminous, high-contrast, it is ultra-thin, can Flexible Displays, low-power consumption, wide viewing angle, fast response time, operating temperature range is wide, it is real to be easy to
Many advantages, such as existing 3D display, " fantasy display " is referred to as by professional, will turn into following most potential new
Type Display Technique.
Certainly, the behind that OLED technology is advanced by leaps and bounds, luminous organic material play an important role.Luminous organic material root
It can be substantially divided into three classes according to luminescence mechanism：Conventional fluorescent material, phosphor material and hot activation delayed fluorescence (Thermally
Activated Delayed Fluorescence, TADF) material.Wherein, conventional fluorescent material and phosphor material are in work
Industry metaplasia production in be applied, but they still have it is clearly disadvantageous.Traditional fluorescent material, in the condition of electroexcitation
Under, limited by spin quantum statistical theorem, singlet excitons and the triplet exciton ratio of number of formation are 1：3,75%
Triplet exciton can only be dissipated and can not be lighted by radiation transistion in the form of heat, only 25% singlet excitons can
Lighted by radiation transistion, i.e., traditional fluorescent material highest internal quantum efficiency (Internal Quantum Efficiency,
IQE it is only) 25%, if being 20% in view of optical coupling delivery efficiency, then the highest external quantum efficiency of its OLED
(External Quantum Efficiency, EQE) is only 5%.Although fluorescent material OLED has higher reliability
And stability, but relatively low external quantum efficiency still limits its application.And phosphor material generally comprises rare precious metals, cause
The problems such as expensive, and device stability can be poor, device efficiency decline is serious, all largely further limit
Its extensive commercial popularization.In recent years, hot activation delayed fluorescence material has been increasingly becoming the new focus of this area research.The material
100% internal quantum efficiency can be realized under conditions of non precious metal, can not only avoid the use of the heavy metal of costliness, from
And cost is reduced to a certain extent, and it can be desirable to greatly improve device lifetime and spectrum stability, while there is luminous effect
Rate is high, the advantage such as environment-friendly, is referred to as third generation electroluminescent material.
But the correlative study at present on hot activation delayed fluorescence material is also fewer, material category is still single, nothing
Method meets the exploitation demand of OLED, and novel high-performance hot activation delayed fluorescence material is urgently developed.
The content of the invention
In view of this, hot activation delayed fluorescence material category is single in order to solve in the prior art, can not meet OLED devices
The technical problem of part demand, the present invention provide a kind of hot activation delayed fluorescence material and its organic electroluminescence based on purine derivative
Luminescent device.
Present invention firstly provides a kind of hot activation delayed fluorescence material based on purine derivative, has such as formula (I) institute
The structural formula shown：
Wherein, Ar1、Ar2Independently selected from H, substituted or unsubstituted C6-C60 arylamine, substituted or unsubstituted C4-
Any one in C60 heteroaromatic.
Preferably, the Ar1、Ar2Independently selected from H, substituted or unsubstituted C6-C30 arylamine, substitution or unsubstituted
C4-C30 heteroaromatic in any one.
Preferably, any one of the Ar in H or following structures：
Wherein, R1、R2Alkyl independently selected from C1-C10, one kind in substituted or unsubstituted C6-C30 aryl；
R3、R4Alkyl independently selected from H, C1-C10, one kind in substituted or unsubstituted C6-C30 aryl, or R3Or R4With
The group at place forms condensed ring.
Preferably, the hot activation delayed fluorescence material based on purine derivative, appointing in following compound 1-20
Shown in meaning one kind：
The present invention also provides a kind of organic electroluminescence device, including anode, negative electrode and positioned at the anode and negative electrode
Between several organic function layers, the organic function layer include it is described based on purine derivative hot activation delay it is glimmering
Luminescent material any one or at least two combination.
Preferably, the organic function layer includes luminescent layer, and the luminescent layer includes described based on purine derivative
Hot activation delayed fluorescence material any one or at least two combination.
Preferably, the hot activation delayed fluorescence material based on purine derivative be used as in luminescent layer dopant material,
Co-doped material or material of main part.
Beneficial effects of the present invention：
Hot activation delayed fluorescence material category is single in order to solve in the prior art, can not meet the skill of OLED demand
Art problem, the present invention provide a kind of hot activation delayed fluorescence material and its organic electroluminescence device based on purine derivative.
The present invention is hexa-atomic thick and fragrant with arylamine or containing nitrogen-atoms using phenyl ring as connecting bridge using purine derivative as electron acceptor
Heterocycle makes to have electrophilic and electron donating group in molecule concurrently, realizes HOMO and LUMO electron cloud separation, have as electron donor
The induction of effect ground produces Intramolecular electron transfer, is advantageous to carrier and transmits in the devices, and then improves organic electroluminescence device
The characteristics of luminescence.
Test result indicates that prepared using the hot activation delayed fluorescence material provided by the invention based on purine derivative
Organic electroluminescence device, external quantum efficiency is high, and maximum current efficiency is reachable up to 12.04cd/A, maximum power efficiency
11.30lm/W there is higher luminous efficiency, and driving voltage is low, is a kind of excellent OLED material.
Embodiment
For a further understanding of the present invention, the preferred embodiment of the invention is described with reference to embodiment, still
It should be appreciated that these descriptions are simply further explanation the features and advantages of the present invention, rather than to the claims in the present invention
Limitation.
It should be noted that unless otherwise prescribed, the implication of scientific and technical terminology used in the present invention and people in the art
The implication that member is generally understood is identical.
Alkyl of the present invention refers to minus the alkyl that a hydrogen atom forms in alkane molecule, and it can be straight chain alkane
Base, branched alkyl or cycloalkyl, example may include methyl, ethyl, propyl group, isopropyl, normal-butyl, isobutyl group, sec-butyl, tertiary fourth
Base, amyl group, isopentyl, cyclopenta, cyclohexyl etc., but not limited to this.
Arylamine of the present invention can be monocyclic diaryl-amine, polycyclic diaryl-amine or monocyclic and polycyclic diaryl-amine.
Aryl of the present invention refers to after removing a hydrogen atom on the aromatic core carbon of aromatic hydrocarbon molecule, is left the total of univalent perssad
Claiming, it can be monocyclic aryl or fused ring aryl, and example may include phenyl, xenyl, naphthyl, anthryl, phenanthryl or pyrenyl etc., but
Not limited to this.
Heteroaromatic of the present invention refers to the total of the group that one or more aromatic core carbon substitute to obtain by hetero atom in aromatic ring
Claim, the hetero atom includes but is not limited to oxygen, sulphur, nitrogen or silicon atom, and the heteroaromatic can be monocyclic or condensed ring, and example can wrap
Include pyridine radicals, phenothiazinyl, phenoxazine base, pyrimidine radicals, benzo pyrimidine radicals, carbazyl, triazine radical, benzothiazolyl, benzo miaow
Oxazolyl, acridinyl etc., but not limited to this.
Present invention firstly provides the hot activation delayed fluorescence material based on purine derivative, has the knot as shown in formula (I)
Structure formula：
Wherein, Ar1、Ar2Independently selected from H, substituted or unsubstituted C6-C60 arylamine, substituted or unsubstituted C4-
Any one in C60 heteroaromatic.
According to the present invention, preferably Ar1、Ar2Independently selected from H, substituted or unsubstituted C6-C30 arylamine, substitution or not
Any one in substituted C4-C30 heteroaromatic.Hetero atom in the heteroaromatic is preferably one kind in N, O, S and Si
Or two kinds；Further, the heteroaromatic is preferably hexa-atomic thick and heteroaromatic.
According to the present invention, further preferably described Ar1、Ar2Any one in H or following structures：
Wherein, R1、R2Alkyl independently selected from C1-C10, one kind in substituted or unsubstituted C6-C30 aryl；
R3、R4Alkyl independently selected from H, C1-C10, one kind in substituted or unsubstituted C6-C30 aryl, or R3Or R4With
The group at place forms condensed ring.Preferably, R1、R2Independently selected from methyl, ethyl, propyl group, butyl, phenyl, xenyl or three
Phenyl, more preferably methyl, ethyl or phenyl；Preferably, R3、R4Independently selected from H, methyl, ethyl, propyl group, butyl, phenyl
Or xenyl, or R3Or R4Form condensed ring with the group at place, more preferably H, methyl, ethyl or phenyl, or for phenyl with
The group at place forms naphthalene nucleus.
As an example, it is not particularly limited, the hot activation delayed fluorescence material of the present invention based on purine derivative is such as
Shown in lower：
It is enumerated above some specific knots of the hot activation delayed fluorescence material of the present invention based on purine derivative
Configuration formula, but the invention is not limited in these listed chemical constitution, every based on structure shown in formula (I), Ar1、Ar2
It should be all included for group as defined above.
The present invention is using purine derivative as electron acceptor, using phenyl ring as connecting bridge, with arylamine or six containing nitrogen-atoms
Member is thick and heteroaromatic is as electron donor, makes to have electrophilic and electron donating group in molecule concurrently, realizes HOMO and LUMO electronics
Cloud separates, and effectively induction produces Intramolecular electron transfer, is advantageous to carrier and transmits in the devices, and then improves organic electroluminescence
The characteristics of luminescence of luminescent device.
The preparation method of hot activation delayed fluorescence material of the invention based on purine derivative, can be by by formula (II) Suo Shi
Compound and formula (III) and formula (IV) shown in compound through ullmann reaction obtain shown in formula (I) based on purine derivative
Hot activation delayed fluorescence material.
The present invention does not have particular/special requirement to the reaction condition of above-mentioned reaction, with such reaction well known to those skilled in the art
Normal condition.The present invention has no particular limits to the source of the raw material employed in above-mentioned all kinds of reactions, Ke Yiwei
Commercially available prod is prepared using preparation method well-known to those skilled in the art.Wherein, the Ar1、Ar2Selection it is same
It is upper described, it will not be repeated here.
The present invention also provides a kind of organic electroluminescence device, and the organic electroluminescence device is those skilled in the art
Known organic electroluminescence device, organic electroluminescence device of the present invention include anode, negative electrode and are located at
Several organic function layers between the anode and negative electrode, the organic function layer include described based on purine derivative
Hot activation delayed fluorescence material any one or at least two combination.The organic function layer can include hole and inject
At least one in layer, hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer and electron injecting layer
Layer, preferably described organic function layer include luminescent layer, and the luminescent layer prolongs including the hot activation based on purine derivative
Slow fluorescent material any one or at least two combination.The more preferably described hot activation delayed fluorescence based on purine derivative
Material is used as dopant material, co-doped material or material of main part in luminescent layer.
The substrate in traditional organic electroluminescence device, example can be used in substrate in organic electroluminescence device of the present invention
Such as glass or plastics, it is preferred that use glass substrate in the present invention.
The electrode material with big work function can be used in anode material, can be such as indium oxide, zinc oxide, tin indium oxide
(ITO), metal oxide of indium zinc oxide (IZO) or its mixture etc..Preferably, tin indium oxide is used in the present invention
(ITO) it is used as anode material.
Hole transmission layer can use various tri-arylamine group materials.Preferably, NPB is used in the present invention.
Cathode material can be used with low work function electrode material, metal or its mixture structure can be used, as Mg,
Ag, Ca or electron injecting layer/metal-layer structure, such as LiF/Al, Li2The common cathode structure such as O/Al.Preferably, originally
The electron injection material used in invention is LiF, and negative electrode is Al.
The present invention has no particular limits to the source of the raw material employed in following examples, can be commercially available prod or
It is prepared using preparation method well-known to those skilled in the art.
Embodiment 1：The synthesis of compound 1
First, by 7,8- diphenyl -1,7- dihydro -6H- purine (0.017mol, 5g), 10- (4- bromobenzenes) -9,9- diformazans
Base acridine (0.017mol, 9.71g) is placed in round-bottomed flask, addition 30mL toluene, iodate Asia ketone, potassium phosphate, and trans 1,2 hexamethylenes
Diamines, is passed through nitrogen protection, and reaction overnight, stops reaction afterwards.Product after drying, is carried by extraction with column chromatography
It is pure, obtain 4.03g products.Yield：41.5%.
Mass spectrum m/z：571.35 (calculated values：571.24).Theoretical elemental content (%) C38H29N5O：C, 79.84；H, 5.11；
N, 12.25；O, 2.80 actual measurement constituent contents (%)：C, 79.88；H, 5.15；N, 12.26；O, 2.80.
Embodiment 2：The synthesis of compound 3
The step of synthesis step is with embodiment 1, simply by a kind of raw material 10- (4- bromobenzenes) -9,9- dimethyl a word used for translations therein
10- (4- bromobenzenes) -10H- phenthazine is changed into pyridine.
Mass spectrum m/z：561.21 (calculated values：561.16).Theoretical elemental content (%) C35H23N5OS：C, 74.85；H,
4.13；N, 12.47；O, 2.85；S, 5.71 actual measurement constituent contents (%)：C, 74.91；H, 4.12；N, 12.48；O, 2.86；S,
5.70。
Embodiment 3：The synthesis of compound 4
The step of synthesis step is with embodiment 1, simply by a kind of raw material 10- (4- bromobenzenes) -9,9- dimethyl a word used for translations therein
10- (4- bromobenzenes) -10H- phenoxazines are changed into pyridine.
Mass spectrum m/z：549.28 (calculated values：545.19).Theoretical elemental content (%) C35H23N5O2：C, 77.05；H,
4.25；N, 12.84；O, 5.86 actual measurement constituent contents (%)：C, 77.10；H, 4.29；N, 12.83；O, 5.87.
Embodiment 4：The synthesis of compound 7
The step of synthesis step is with embodiment 1, simply by a kind of raw material 10- (4- bromobenzenes) -9,9- dimethyl a word used for translations therein
N- (4- bromobenzenes)-N- phenyl napthyl -1- amine is changed into pyridine.
Mass spectrum m/z：581.32 (calculated values：581.22).Theoretical elemental content (%) C39H27N5O：C, 80.53；H, 4.68；
N, 12.04；O, 2.75 actual measurement constituent contents (%)：C, 80.59；H, 4.65；N, 12.08；O, 2.76.
Embodiment 5：The synthesis of compound 8
The step of synthesis step is with embodiment 1, simply by a kind of raw material 10- (4- bromobenzenes) -9,9- dimethyl a word used for translations therein
The bromo- N of 4-, N- diphenyl aniline are changed into pyridine.
Mass spectrum m/z：531.28 (calculated values：531.21).Theoretical elemental content (%) C35H25N5O：C, 79.08；H, 4.74；
N, 13.17；O, 3.01 actual measurement constituent contents (%)：C, 79.19；H, 4.73；N, 13.15；O, 3.05.
Embodiment 6：The synthesis of compound 11
First, by 8- phenyl -1,7- dihydro -6H- purine (0.024mol, 5g), 10- (4- bromobenzenes) -9,9- dimethyl a word used for translations
Pyridine (0.048mol, 17.12g) is placed in round-bottomed flask, adds 30mL toluene, iodate Asia ketone, potassium phosphate, trans 1,2 hexamethylenes two
Amine, is passed through nitrogen protection, and reaction overnight, stops reaction afterwards.Product after dry, is purified by extracting with column chromatography,
Obtain 11.21g products.Yield：60.0%.
Mass spectrum m/z：778.48 (calculated values：778.34).Theoretical elemental content (%) C53H42N6O：C, 81.72；H, 5.43；
N, 10.79；O, 2.05 actual measurement constituent contents (%)：C, 81.79；H, 5.44；N, 10.75；O, 2.08.
Embodiment 7：The synthesis of compound 13
Synthesis step is same as the step of embodiment 1, simply by a kind of raw material 10- (4- bromobenzenes) -9,9- dimethyl therein
Acridine changes into 10- (4- bromobenzenes) -10H- phenthazine.
Mass spectrum m/z：758.28 (calculated values：758.19).Theoretical elemental content (%) C47H30N6OS2：C, 74.38；H,
3.98；N, 11.07；O, 2.11；S, 8.45 actual measurement constituent contents (%)：C, 74.49；H, 4.03；N, 11.05；O, 2.15；S,
8.46。
Embodiment 8：The synthesis of compound 14
Synthesis step is same as the step of embodiment 1, simply by a kind of raw material 10- (4- bromobenzenes) -9,9- dimethyl therein
Acridine changes into 10- (4- bromobenzenes) -10H- phenoxazines.
Mass spectrum m/z：726.38 (calculated values：726.24).Theoretical elemental content (%) C47H30N6O3：C, 77.67；H,
4.16；N, 11.56；O, 6.60 actual measurement constituent contents (%)：C, 77.76；H, 4.13；N, 11.55；O, 6.65.
Embodiment 9：The synthesis of compound 15
Synthesis step is same as the step of embodiment 1, simply by a kind of raw material 10- (4- bromobenzenes) -9,9- dimethyl therein
Acridine changes into N- (4- bromobenzenes)-N- phenyl napthyl -1- amine.
Mass spectrum m/z：798.42 (calculated values：798.31).Theoretical elemental content (%) C55H38N6O：C, 82.68；H, 4.79；
N, 10.52；O, 2.00 actual measurement constituent contents (%)：C, 82.73；H, 4.73；N, 10.55；O, 2.02.
Embodiment 10：The synthesis of compound 16
Synthesis step is same as the step of embodiment 1, simply by a kind of raw material 10- (4- bromobenzenes) -9,9- dimethyl therein
Acridine changes into the bromo- N of 4-, N- diphenyl aniline.
Mass spectrum m/z：698.40 (calculated values：698.28).Theoretical elemental content (%) C47H34N6O：C, 80.78；H, 4.90；
N, 12.03；O, 2.29 actual measurement constituent contents (%)：C, 80.83；H, 4.93；N, 12.05；O, 2.31.
Embodiment 11：The preparation of organic electroluminescence device
The glass substrate for being coated with ito transparent electrode is ultrasonically treated in commercial detergent, rinsed in deionized water,
In acetone：Ultrasonic oil removing in alcohol mixed solvent, it is baked in clean environment and removes moisture completely, it is clear with ultraviolet light and ozone
Wash.
The above-mentioned glass substrate for being coated with ito transparent electrode is placed in vacuum chamber, is evacuated to 10-5–10-3Pa, evaporation
Hole transmission layer NPB, evaporation rate 0.1nm/s, thickness 20nm.On hole transmission layer be deposited the present invention in based on fast
The hot activation delayed fluorescence material of purine derivative is as luminescent layer, evaporation rate 0.1nm/s, thickness 30nm.In luminescent layer
Upper one layer of AlQ of vacuum evaporation3As electron transfer layer, evaporation rate 0.1nm/s, thickness 20nm.On the electron transport layer
Electron injecting layers and negative electrode of the LiF and Al as device, thickness difference 1nm and 100nm is deposited.The luminescent properties of measurement device,
It the results are shown in Table 1.
The characteristics of luminescence of luminescent device prepared by the embodiment of the present invention of table 1
As can be seen that prepared using the hot activation delayed fluorescence material provided by the invention based on purine derivative organic
Electroluminescent device, external quantum efficiency is high, and maximum current efficiency is up to 12.04cd/A, and maximum power efficiency is up to 11.30lm/
W, there is higher luminous efficiency, and driving voltage is low, is a kind of excellent OLED material.
Obviously, the explanation of above example is only intended to help the method and its core concept for understanding the present invention.It should refer to
Go out, under the premise without departing from the principles of the invention, can also be to this hair for the those of ordinary skill of the technical field
Bright to carry out some improvement and modification, these are improved and modification is also fallen into the protection domain of the claims in the present invention.
Claims (7)
1. the hot activation delayed fluorescence material based on purine derivative, there is the structural formula as shown in formula (I)：
Wherein, Ar1、Ar2Independently selected from H, substituted or unsubstituted C6-C60 arylamine, substituted or unsubstituted C4-C60
Any one in heteroaromatic.
2. the hot activation delayed fluorescence material according to claim 1 based on purine derivative, it is characterised in that Ar1、Ar2
Independently selected from H, substituted or unsubstituted C6-C30 arylamine, substituted or unsubstituted C4-C30 heteroaromatic in it is any one
Kind.
3. the hot activation delayed fluorescence material according to claim 1 based on purine derivative, it is characterised in that Ar1、Ar2
Any one in H or following structures：
Wherein, R1、R2Alkyl independently selected from C1-C10, one kind in substituted or unsubstituted C6-C30 aryl；R3、R4Solely
On the spot one kind in the alkyl selected from H, C1-C10, substituted or unsubstituted C6-C30 aryl, or R3Or R4With the base at place
Group forms condensed ring.
4. the hot activation delayed fluorescence material according to claim 1 based on purine derivative, it is characterised in that followingization
Shown in any one of compound：
5. a kind of organic electroluminescence device, including anode, negative electrode and several between the anode and negative electrode have
Machine functional layer, it is characterised in that the organic function layer includes deriving based on purine described in any one of Claims 1 to 4
The hot activation delayed fluorescence material of thing any one or at least two combination.
6. a kind of organic electroluminescence device according to claim 5, it is characterised in that the organic function layer includes hair
Photosphere, the luminescent layer include the hot activation delayed fluorescence material based on purine derivative described in any one of Claims 1 to 4
Any one or at least two combination.
7. a kind of organic electroluminescence device according to claim 6, it is characterised in that described based on purine derivative
Hot activation delayed fluorescence material is used as dopant material, co-doped material or material of main part in luminescent layer.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108219781A (en) * | 2018-04-02 | 2018-06-29 | 长春海谱润斯科技有限公司 | The hot activation delayed fluorescence material and its organic electroluminescence device of a kind of tetrazine derivatives |
| CN109651370A (en) * | 2018-12-17 | 2019-04-19 | 桂林理工大学 | A kind of purine analog derivative free radical precursor molecule and preparation method thereof |
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2017
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108219781A (en) * | 2018-04-02 | 2018-06-29 | 长春海谱润斯科技有限公司 | The hot activation delayed fluorescence material and its organic electroluminescence device of a kind of tetrazine derivatives |
| CN109651370A (en) * | 2018-12-17 | 2019-04-19 | 桂林理工大学 | A kind of purine analog derivative free radical precursor molecule and preparation method thereof |
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