CN103435597A - 1,3, 5-triazine derivative and application thereof in white organic electroluminescent diode - Google Patents
1,3, 5-triazine derivative and application thereof in white organic electroluminescent diode Download PDFInfo
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- CN103435597A CN103435597A CN2013103977752A CN201310397775A CN103435597A CN 103435597 A CN103435597 A CN 103435597A CN 2013103977752 A CN2013103977752 A CN 2013103977752A CN 201310397775 A CN201310397775 A CN 201310397775A CN 103435597 A CN103435597 A CN 103435597A
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- Prior art keywords
- phenanthroline
- substituted
- group
- tert
- butyl
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- 125000003363 1,3,5-triazinyl group Chemical class N1=C(N=CN=C1)* 0.000 title claims abstract 11
- 239000000463 material Substances 0.000 claims abstract description 96
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 238000002360 preparation method Methods 0.000 claims abstract description 11
- -1 n- heptyl Chemical group 0.000 claims description 449
- 125000003118 aryl group Chemical group 0.000 claims description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000003107 substituted aryl group Chemical group 0.000 claims description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 230000005525 hole transport Effects 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 6
- 239000012046 mixed solvent Substances 0.000 claims description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- YCEZZDNWLVQCRU-UHFFFAOYSA-N 1,2-diaminoethyl Chemical group N[CH]CN YCEZZDNWLVQCRU-UHFFFAOYSA-N 0.000 claims description 2
- LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000006083 1-bromoethyl group Chemical group 0.000 claims description 2
- 125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 claims description 2
- 125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 claims description 2
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 claims description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 claims description 2
- 125000005999 2-bromoethyl group Chemical group 0.000 claims description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical group C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 2
- SZPWXAOBLNYOHY-UHFFFAOYSA-N [C]1=CC=NC2=CC=CC=C12 Chemical group [C]1=CC=NC2=CC=CC=C12 SZPWXAOBLNYOHY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000005997 bromomethyl group Chemical group 0.000 claims description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- 238000004440 column chromatography Methods 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000000284 extract Substances 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
- 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 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- MHAUGLFOVCQYNR-UHFFFAOYSA-N pentaphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 MHAUGLFOVCQYNR-UHFFFAOYSA-N 0.000 claims description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 2
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000001725 pyrenyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 claims description 2
- KTQYWNARBMKMCX-UHFFFAOYSA-N tetraphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 KTQYWNARBMKMCX-UHFFFAOYSA-N 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
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- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 claims 1
- HBBKKZVRZMEYOS-UHFFFAOYSA-N 1,8-phenanthroline Chemical compound N1=CC=C2C3=NC=CC=C3C=CC2=C1 HBBKKZVRZMEYOS-UHFFFAOYSA-N 0.000 claims 1
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- 239000002019 doping agent Substances 0.000 abstract description 4
- 238000000034 method Methods 0.000 abstract description 4
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- 238000001704 evaporation Methods 0.000 description 14
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- 239000012043 crude product Substances 0.000 description 8
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 8
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- 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
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- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
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- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 4
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- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
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- XFZZDIHCNHYESF-UHFFFAOYSA-N 7-amino-1-bromo-4-phenyl-5,7,8,9-tetrahydrobenzo[7]annulen-6-one Chemical compound C=12CC(=O)C(N)CCC2=C(Br)C=CC=1C1=CC=CC=C1 XFZZDIHCNHYESF-UHFFFAOYSA-N 0.000 description 3
- 229910001316 Ag alloy Inorganic materials 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
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- 230000009286 beneficial effect Effects 0.000 description 1
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- CUNRCBBBPBWPTM-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c(cc2)ccc2-[n]2c3ccccc3c3c2cccc3)nc(-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c1nc(-c(cc2)ccc2-[n]2c3ccccc3c3c2cccc3)nc(-c2ccccc2)n1 CUNRCBBBPBWPTM-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
本发明公开了一种1,3,5-三嗪衍生物，该衍生物为具有式Ι结构的化合物，
Description
技术领域technical field
本发明涉及有机电致发光材料领域，特别是涉及一种1,3,5-三嗪衍生物及其在白光有机电致发光二极管中的应用。The invention relates to the field of organic electroluminescent materials, in particular to a 1,3,5-triazine derivative and its application in white light organic electroluminescent diodes.
背景技术Background technique
近年来，白光有机电致发光材料和器件的研究受到了国际学术界、政府和产业界的巨大重视，各国和地区如美国、欧洲、日本等纷纷推出重大研究计划（美国Next Generation Lighting Initiative，欧盟OLLA，日本21CenturyLighting Program）来强化这一领域的研究，这是因为，白光有机电致发光技术（WOLED）有望成为新一代最重要的固体光源技术之一。WOLED的理论预测电光转换效率将是目前白炽灯和荧光灯的几倍，甚至十几倍以上，这一技术的发展和广泛使用将对节约能源和保护环境具有重要意义。In recent years, the research on white light organic electroluminescent materials and devices has received great attention from international academic circles, governments and industries. Countries and regions such as the United States, Europe, Japan, etc. have launched major research programs (U.S. Next Generation Lighting Initiative, European Union OLLA, Japan 21Century Lighting Program) to strengthen research in this field, because white organic electroluminescent technology (WOLED) is expected to become one of the most important solid-state light source technologies in the new generation. The theory of WOLED predicts that the electro-optical conversion efficiency will be several times, even more than ten times that of the current incandescent and fluorescent lamps. The development and widespread use of this technology will be of great significance to saving energy and protecting the environment.
在有机电致发光领域中，实现WOLED的途径通常有三种：a）全荧光机制的白光有机电致发光技术（F-WOLED），其发光层由发蓝、绿、红色荧光的材料组成。因为荧光材料只能利用发光层中占激子总数25%的单重态激子，所以该机制的理论内量子效率最高只能达到25%，显然不是一种高效的发光机制。b）全磷光机制的白光有机电致发光技术（P-WOLED），其发光层由发蓝、绿、红色磷光的材料组成。这类发光材料既可利用单重态激子又可利用三重态激子发光，因而该机制的理论内量子效率最高可达100%，是一种高效的发光机制。c）荧光/磷光组合机制的白光有机电致发光技术（F/P-WOLED），其发光层由蓝色荧光材料和绿色、红色磷光材料组成。这两类材料分别利用单重态激子发出蓝色荧光和三重态激子发出绿色、红色磷光，因此这种机制理论内量子效率最高可达到100%，显然也是一种高效的发光机制。同时，与P-WOLED相比，F/P-WOLED使用了蓝色荧光材料代替效率低、稳定性差的蓝色磷光材料，使得器件的寿命得到了提高。因此，F/P-WOLED被认为是最理想和最有希望实现高效率、长寿命的WOLED固体光源技术的途径。In the field of organic electroluminescence, there are usually three ways to realize WOLED: a) white light organic electroluminescence technology (F-WOLED) with full fluorescence mechanism, and its light-emitting layer is composed of materials that emit blue, green, and red fluorescence. Because fluorescent materials can only utilize singlet excitons that account for 25% of the total number of excitons in the light-emitting layer, the theoretical internal quantum efficiency of this mechanism can only reach 25%, which is obviously not an efficient light-emitting mechanism. b) White-light organic electroluminescence technology (P-WOLED) with full phosphorescence mechanism, whose light-emitting layer is composed of blue, green, and red phosphorescent materials. This type of luminescent material can use both singlet excitons and triplet excitons to emit light, so the theoretical internal quantum efficiency of this mechanism can reach up to 100%, which is an efficient luminescence mechanism. c) Fluorescent/phosphorescent combined white light organic electroluminescent technology (F/P-WOLED), whose light-emitting layer is composed of blue fluorescent materials and green and red phosphorescent materials. These two types of materials use singlet excitons to emit blue fluorescence and triplet excitons to emit green and red phosphorescence respectively. Therefore, the theoretical quantum efficiency of this mechanism can reach up to 100%, which is obviously an efficient light-emitting mechanism. At the same time, compared with P-WOLED, F/P-WOLED uses blue fluorescent material instead of blue phosphorescent material with low efficiency and poor stability, so that the lifetime of the device is improved. Therefore, F/P-WOLED is considered to be the most ideal and promising way to realize high-efficiency and long-life WOLED solid-state light source technology.
为了实现单重态激子和三重态激子的有效分离，基于F/P-WOLED的器件的发光层通常包括【主体材料：蓝色荧光材料/主体材料/主体材料：绿色磷光材料/主体材料：红色磷光材料/主体材料/主体材料：蓝色荧光材料】共六层。如果一种材料自身具有高效蓝色荧光发光，并且具有较高三重态能级（高于2.4eV），可同时敏化绿色、红色磷光掺杂材料，那么，由这种可用作主体材料的高效蓝色荧光材料制作的白光器件，其发光层包括【蓝色荧光材料/主体材料：绿色磷光材料/主体材料：红色磷光材料/蓝色荧光材料】共四层，使得基于F/P-WOLED的传统的器件结构得到简化，因而也会进一步提高WOLED的器件性能。In order to achieve efficient separation of singlet and triplet excitons, the light-emitting layer of F/P-WOLED-based devices usually includes [host material: blue fluorescent material / host material / host material: green phosphorescent material / host material : Red Phosphorescent Material/Main Body Material/Main Material: Blue Fluorescent Material] There are six layers in total. If a material itself has high-efficiency blue fluorescence emission, and has a higher triplet energy level (higher than 2.4eV), it can simultaneously sensitize green and red phosphorescent dopant materials, then this can be used as a host material The white light device made of high-efficiency blue fluorescent material, its light-emitting layer includes [blue fluorescent material / host material: green phosphorescent material / host material: red phosphorescent material / blue fluorescent material] a total of four layers, so that based on F/P-WOLED The traditional device structure is simplified, which will further improve the device performance of WOLED.
因此，寻找这种自身发高效的蓝色荧光，同时具有较高的三重态能级（高于2.4eV）的材料成为问题的关键。Therefore, finding such a material that emits efficient blue fluorescence and has a higher triplet energy level (higher than 2.4eV) becomes the key to the problem.
发明内容Contents of the invention
本发明所要解决的技术问题是提供一种1,3,5-三嗪衍生物，由本发明提供的1,3,5-三嗪衍生物的发光材料在实现自身发高效的蓝色荧光的同时，还能敏化绿色和红色磷光掺杂材料，满足制备WOLED的工艺条件。The technical problem to be solved by the present invention is to provide a 1,3,5-triazine derivative. The luminescent material of the 1,3,5-triazine derivative provided by the present invention realizes efficient blue fluorescence by itself , can also sensitize green and red phosphorescent dopant materials, and meet the process conditions for preparing WOLEDs.
本发明所要解决的第二个技术问题是提供1,3,5-三嗪衍生物的制备方法。The second technical problem to be solved by the present invention is to provide a preparation method of 1,3,5-triazine derivatives.
本发明所要解决的第三个技术问题是使用所述1,3,5-三嗪衍生物制备的白光发光二极管。The third technical problem to be solved by the present invention is the white light emitting diode prepared by using the 1,3,5-triazine derivative.
为解决上述第一个技术问题，本发明采用的技术方案是提供一种1,3,5-三嗪衍生物，所述1,3,5-三嗪衍生物为具有如式Ⅰ所示结构的化合物，In order to solve the first technical problem above, the technical solution adopted by the present invention is to provide a 1,3,5-triazine derivative, which has the structure shown in formula I compound of,
式(Ι)中In formula (Ι)
式Ⅰ中，R1、R2相同或不同，选自氢、氟、烷基、环烷基、取代烷基、芳烷基、未取代或取代芳基、未取代或取代杂芳基；In formula I, R 1 and R 2 are the same or different, selected from hydrogen, fluorine, alkyl, cycloalkyl, substituted alkyl, aralkyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl;
式Ⅰ中，R3、R4相同或不同，选自烷基、环烷基、取代烷基、芳烷基、未取代或取代芳基、未取代或取代杂芳基；X为杂原子，优选地，X选自N、S或O；In formula I, R 3 and R 4 are the same or different, selected from alkyl, cycloalkyl, substituted alkyl, aralkyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl; X is a heteroatom, Preferably, X is selected from N, S or O;
式Ⅰ中，Ar选自未取代或取代芳基、未取代或取代杂芳基。In formula I, Ar is selected from unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl.
所述烷基为具有1至20个碳原子的烷基；The alkyl group is an alkyl group having 1 to 20 carbon atoms;
所述环烷基为具有3至20个碳原子的环烷基；The cycloalkyl group is a cycloalkyl group having 3 to 20 carbon atoms;
所述取代烷基为卤素取代的1至20个碳原子的烷基、羟基取代的1至20个碳原子的烷基、氰基取代的1至20个碳原子的烷基、硝基取代的1至20个碳原子的烷基或者氨基取代的1至20个碳原子的烷基；The substituted alkyl group is an alkyl group of 1 to 20 carbon atoms substituted by a halogen, an alkyl group of 1 to 20 carbon atoms substituted by a hydroxyl group, an alkyl group of 1 to 20 carbon atoms substituted by a cyano group, a nitro group substituted An alkyl group of 1 to 20 carbon atoms or an alkyl group of 1 to 20 carbon atoms substituted by an amino group;
所述芳烷基为芳基取代的1至20个碳原子的烷基；The aralkyl group is an alkyl group of 1 to 20 carbon atoms substituted by an aryl group;
所述R1、R2、R3和R4中的未取代或取代芳基为具有6至50个芳族环原子的芳基；The unsubstituted or substituted aryl group in R 1 , R 2 , R 3 and R 4 is an aryl group with 6 to 50 aromatic ring atoms;
所述R1、R2、R3和R4中的未取代或取代杂芳基为具有5至50个芳族环原子的芳族杂环基团；The unsubstituted or substituted heteroaryl group in R 1 , R 2 , R 3 and R 4 is an aromatic heterocyclic group with 5 to 50 aromatic ring atoms;
所述Ar中的取代或未取代芳基为具有6至28个芳族环原子的芳基；The substituted or unsubstituted aryl group in Ar is an aryl group with 6 to 28 aromatic ring atoms;
所述Ar中的取代或未取代杂芳基为具有5至21个芳族环原子的芳基；The substituted or unsubstituted heteroaryl in Ar is an aryl group with 5 to 21 aromatic ring atoms;
3.根据权利要求2所述的1,3,5-三嗪衍生物，其特征在于：3. 1,3,5-triazine derivatives according to claim 2, characterized in that:
所述具有1至20个碳原子的烷基为甲基、乙基、丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、正己基、正庚基或正辛基；The alkyl group having 1 to 20 carbon atoms is methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n- Heptyl or n-octyl;
所述具有3至20个碳原子的环烷基为环丙基、环丁基、环戊基、环己基、4-甲基环己基、金刚烷基或降冰片烷基；The cycloalkyl group having 3 to 20 carbon atoms is cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, adamantyl or norbornyl;
所述具有1至20个碳原子的取代烷基为羟甲基、1-羟乙基、2-羟乙基、2-羟异丁基、1,2-二羟基乙基、1,3-二羟基异丙基、2,3-二羟基-叔丁基、1,2,3-三羟基丙基、氟甲基、1-氟乙基、2-氟乙基、2-氟异丁基、1,2-二氟乙基、1,3-二氟异丙基、2,3-二氟-叔丁基、1,2,3-三氟丙基、氯甲基、1-氯乙基、2-氯乙基、2-氯异丁基、1,2-二氯乙基、1,3-二氯异丙基、2,3-二氯-叔丁基、1,2,3-三氯丙基、溴甲基、1-溴乙基、2-溴乙基、2-溴异丁基、1,2-二溴乙基、1,3-二溴异丙基、2,3-二溴-叔丁基、1,2,3-三溴丙基、碘甲基、1-碘乙基、2-碘乙基、2-碘异丁基、1,2-二碘乙基、1,3-二碘异丙基、2,3-二碘-叔丁基、1,2,3-三碘丙基、氨基甲基、1-氨基乙基、2-氨基乙基、2-氨基异丁基、1,2-二氨基乙基、1,3-二氨基异丙基、2,3-二氨基-叔丁基或1,2,3-三氨基丙基；氰基甲基、1-氰基乙基、2-氰基乙基、2-氰基异丁基、1,2-二氰基乙基、1,3-二氰基异丙基、2,3-二氰基-叔丁基、1,2,3-三氰基丙基、硝基甲基、1-硝基乙基、2-硝基乙基、2-硝基异丁基、1,2-二硝基乙基、1,3-二硝基异丙基、2,3-二硝基-叔丁基或1,2,3-三硝基丙基；The substituted alkyl group having 1 to 20 carbon atoms is hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxyisobutyl, 1,2-dihydroxyethyl, 1,3- Dihydroxyisopropyl, 2,3-dihydroxy-tert-butyl, 1,2,3-trihydroxypropyl, fluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2-fluoroisobutyl , 1,2-difluoroethyl, 1,3-difluoroisopropyl, 2,3-difluoro-tert-butyl, 1,2,3-trifluoropropyl, chloromethyl, 1-chloroethyl Base, 2-chloroethyl, 2-chloroisobutyl, 1,2-dichloroethyl, 1,3-dichloroisopropyl, 2,3-dichloro-tert-butyl, 1,2,3 -Trichloropropyl, bromomethyl, 1-bromoethyl, 2-bromoethyl, 2-bromoisobutyl, 1,2-dibromoethyl, 1,3-dibromoisopropyl, 2, 3-Dibromo-tert-butyl, 1,2,3-tribromopropyl, iodomethyl, 1-iodoethyl, 2-iodoethyl, 2-iodoisobutyl, 1,2-diiodoethyl Base, 1,3-diiodoisopropyl, 2,3-diiodo-tert-butyl, 1,2,3-triiodopropyl, aminomethyl, 1-aminoethyl, 2-aminoethyl, 2-aminoisobutyl, 1,2-diaminoethyl, 1,3-diaminoisopropyl, 2,3-diamino-tert-butyl or 1,2,3-triaminopropyl; cyano Methyl, 1-cyanoethyl, 2-cyanoethyl, 2-cyanoisobutyl, 1,2-dicyanoethyl, 1,3-dicyanoisopropyl, 2,3- Dicyano-tert-butyl, 1,2,3-tricyanopropyl, nitromethyl, 1-nitroethyl, 2-nitroethyl, 2-nitroisobutyl, 1,2 - dinitroethyl, 1,3-dinitroisopropyl, 2,3-dinitro-tert-butyl or 1,2,3-trinitropropyl;
所述芳基取代的1至20个碳原子的烷基为苄基、1-苯基乙基、2-苯基乙基、1-苯基异丙基、2-苯基异丙基、苯基叔丁基、α-萘基甲基、1-α-萘基乙基、2-α-萘基乙基、1-α-萘基异丙基、2-α-萘基异丙基、β-萘基甲基、1-β-萘基乙基、2-β-萘基乙基、1-β-萘基异丙基、2-β-萘基异丙基、1-吡咯基甲基、2-(1-吡咯基)乙基；The alkyl group of 1 to 20 carbon atoms substituted by the aryl group is benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, benzene tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, 1-pyrrolylmethyl Base, 2-(1-pyrrolyl) ethyl;
所述具有R1、R2、R3和R4中的未取代或取代6至50个芳族环原子的芳基为苯基、1-萘基、2-萘基、1-蒽基、2-蒽基、9-蒽基、1-菲基、2-菲基、3-菲基、4-菲基、9-菲基、1-并四苯基、2-并四苯基、9-并四苯基、1-芘基、2-芘基、4-芘基、2-联苯基、3-联苯基、4-联苯基、对三联苯-4-基、对三联苯-3-基、对三联苯-2-基、间三联苯-4-基、间三联苯-3-基、间三联苯-2-基、邻甲苯基、间甲苯基、对甲苯基、对叔丁基苯基、对-(2-苯基丙基)苯基、3-甲基-2-萘基、4-甲基-1-萘基、4-甲基-1-萘基、4’-甲基联苯基或4”-叔丁基-对三联苯-4-基；The aryl group having unsubstituted or substituted 6 to 50 aromatic ring atoms among R 1 , R 2 , R 3 and R 4 is phenyl, 1-naphthyl, 2-naphthyl, 1-anthracenyl, 2 -Anthracenyl, 9-anthryl, 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 9-phenanthrenyl, 1-tetraphenyl, 2-phenanthrenyl, 9- Naphthacene, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, p-terphenyl-4-yl, p-terphenyl- 3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-tert Butylphenyl, p-(2-phenylpropyl)phenyl, 3-methyl-2-naphthyl, 4-methyl-1-naphthyl, 4-methyl-1-naphthyl, 4' - methylbiphenyl or 4"-tert-butyl-p-terphenyl-4-yl;
所述R1、R2、R3和R4中的未取代或取代具有5至50个芳族环原子的杂芳基为2-吡咯基、3-吡咯基、吡啶基、2-吡啶基、3-吡啶基、4-吡啶基、2-吲哚基、3-吲哚基、4-吲哚基、5-吲哚基、6-吲哚基、7-吲哚基、1-异吲哚基、3-异吲哚基、4-异吲哚基、5-异吲哚基、6-异吲哚基、7-异吲哚基、2-呋喃基、3-呋喃基、2-苯并呋喃基、3-苯并呋喃基、4-苯并呋喃基、5-苯并呋喃基、6-苯并呋喃基、7-苯并呋喃基、1-异苯并呋喃基、3-异苯并呋喃基、4-异苯并呋喃基、5-异苯并呋喃基、6-异苯并呋喃基、7-异苯并呋喃基、2-喹啉基、3-喹啉基、4-喹啉基、5-喹啉基、6-喹啉基、7-喹啉基、8-喹啉基、1-异喹啉基、3-异喹啉基、4-异喹啉基、5-异喹啉基、6-异喹啉基、7-异喹啉基、8-异喹啉基、2-喹喔啉基、5-喹喔啉基、6-喹喔啉基、1-咔唑基、2-咔唑基、3-咔唑基、4-咔唑基、2-(9H-咔唑基)苯基，3-(9H-咔唑基)苯基，4-(9H-咔唑基)苯基，2-三苯胺基，3-三苯胺基，4-三苯胺基，1-菲啶基、2-菲啶基、3-菲啶基、4-菲啶基、6-菲啶基、7-菲啶基、8-菲啶基、9-菲啶基、10-菲啶基、1-吖啶基、2-吖啶基、3-吖啶基、4-吖啶基、9-吖啶基、1,7-菲咯琳-2-基、1,7-菲咯琳-3-基、1,7-菲咯琳-4-基、1,7-菲咯琳-5-基、1,7-菲咯琳-6-基、1,7-菲咯琳-8-基、1,7-菲咯琳-9-基、1,7-菲咯琳-10-基、1,8-菲咯琳-2-基、1,8-菲咯琳-3-基、1,8-菲咯琳-4-基、1,8-菲咯琳-5-基、1,8-菲咯琳-6-基、1,8-菲咯琳-7-基、1,8-菲咯琳-9-基、1,8-菲咯琳-10-基、1,9-菲咯琳-2-基、1,9-菲咯琳-3-基、1,9-菲咯琳-4-基、1,9-菲咯琳-5-基、1,9-菲咯琳-6-基、1,9-菲咯琳-7-基、1,9-菲咯琳-8-基、1,9-菲咯琳-10-基、1,10-菲咯琳-2-基、1,10-菲咯琳-3-基、1,10-菲咯琳-4-基、1,10-菲咯琳-5-基、2,9-菲咯琳-1-基、2,9-菲咯琳-3-基、2,9-菲咯琳-4-基、2,9-菲咯琳-5-基、2,9-菲咯琳-6-基、2,9-菲咯琳-7-基、2,9-菲咯琳_8-基、2,9-菲咯琳-10-基、2,8-菲咯琳-1-基、2,8-菲咯琳-3-基、2,8-菲咯琳-4-基、2,8-菲咯琳-5-基、2,8-菲咯琳-6-基、2,8-菲咯琳-7-基、2,8-菲咯琳-9-基、2,8-菲咯琳-10-基、2,7-菲咯琳-1-基、2,7-菲咯琳-3-基、2,7-菲咯琳-4-基、2,7-菲咯琳-5-基、2,7-菲咯琳-6-基、2,7-菲咯琳-8-基、2,7-菲咯琳-9-基、2,7-菲咯琳-10-基、1-吩嗪基、2-吩嗪基、1-吩噻嗪基、2-吩噻嗪基、3-吩噻嗪基、4-吩噻嗪基、1-吩噁嗪基、2-吩噁嗪基、3-吩噁嗪基、4-吩噁嗪基、2-噁唑.基、4-噁唑基、5-噁唑基、2-噁二唑基、5-噁二唑基、3-呋咱基、2-噻吩基、3-噻吩基、2-苯并噻吩基、3-苯并噻吩基、4-苯并噻吩基、5-苯并噻吩基、6-苯并噻吩基、7-苯并噻吩基、1-异苯并噻吩基、3-异苯并噻吩基、4-异苯并噻吩基、5-异苯并噻吩基、6-异苯并噻吩基、7-异苯并噻吩基、2-甲基吡咯-1-基、2-甲基吡咯-3-基、2-甲基吡咯-4-基、2-甲基吡咯-5-基、3-甲基吡咯-1-基、3-甲基吡咯-2-基、3-甲基吡咯-4-基、3-甲基吡咯-5-基、2-叔丁基吡咯-4-基、3-(2-苯基丙基)吡咯-1-基、2-甲基-1-吲哚基、4-甲基-1-吲哚基、2-甲基-3-吲哚基、4-甲基-3-吲哚基、2-叔丁基-1-吲哚基、4-叔丁基-1-吲哚基、2-叔丁基-3-吲哚基或4-叔丁基-3-吲哚基。The unsubstituted or substituted heteroaryl with 5 to 50 aromatic ring atoms in R 1 , R 2 , R 3 and R 4 is 2-pyrrolyl, 3-pyrrolyl, pyridyl, 2-pyridyl , 3-pyridyl, 4-pyridyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-iso Indolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2 -benzofuryl, 3-benzofuryl, 4-benzofuryl, 5-benzofuryl, 6-benzofuryl, 7-benzofuryl, 1-isobenzofuryl, 3 -isobenzofuryl, 4-isobenzofuryl, 5-isobenzofuryl, 6-isobenzofuryl, 7-isobenzofuryl, 2-quinolyl, 3-quinolyl , 4-quinolinyl, 5-quinolinyl, 6-quinolinyl, 7-quinolinyl, 8-quinolinyl, 1-isoquinolinyl, 3-isoquinolinyl, 4-isoquinolinyl Base, 5-isoquinolinyl, 6-isoquinolinyl, 7-isoquinolinyl, 8-isoquinolinyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl , 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 2-(9H-carbazolyl)phenyl, 3-(9H-carbazolyl)phenyl, 4 -(9H-carbazolyl)phenyl, 2-triphenylamino, 3-triphenylamino, 4-triphenylamino, 1-phenanthridine, 2-phenanthridine, 3-phenanthridine, 4-phenanthrene Pyridyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl , 4-acridinyl, 9-acridinyl, 1,7-phenanthroline-2-yl, 1,7-phenanthroline-3-yl, 1,7-phenanthroline-4-yl, 1 ,7-phenanthroline-5-yl, 1,7-phenanthroline-6-yl, 1,7-phenanthroline-8-yl, 1,7-phenanthroline-9-yl, 1,7 -Phenanthroline-10-yl, 1,8-phenanthroline-2-yl, 1,8-phenanthroline-3-yl, 1,8-phenanthroline-4-yl, 1,8-phenanthrene phenanthroline-5-yl, 1,8-phenanthroline-6-yl, 1,8-phenanthroline-7-yl, 1,8-phenanthroline-9-yl, 1,8-phenanthroline -10-yl, 1,9-phenanthroline-2-yl, 1,9-phenanthroline-3-yl, 1,9-phenanthroline-4-yl, 1,9-phenanthroline-5 -yl, 1,9-phenanthroline-6-yl, 1,9-phenanthroline-7-yl, 1,9-phenanthroline-8-yl, 1,9-phenanthroline-10-yl , 1,10-phenanthroline-2-yl, 1,10-phenanthroline-3-yl, 1,10-phenanthroline-4-yl, 1,10-phenanthroline-5-yl, 2 ,9-phenanthroline-1-yl, 2,9-phenanthroline-3-yl, 2,9-phenanthroline-4-yl, 2,9-phenanthroline-5-yl, 2,9 -Phenylline-6-yl, 2,9-phenanthroline-7-base, 2,9-phenanthroline-8-base, 2,9-phenanthroline-10-base, 2,8-phenanthrene Caroline-1 -yl, 2,8-phenanthroline-3-yl, 2,8-phenanthroline-4-yl, 2,8-phenanthroline-5-yl, 2,8-phenanthroline-6-yl , 2,8-phenanthroline-7-yl, 2,8-phenanthroline-9-yl, 2,8-phenanthroline-10-yl, 2,7-phenanthroline-1-yl, 2 ,7-phenanthroline-3-yl, 2,7-phenanthroline-4-yl, 2,7-phenanthroline-5-yl, 2,7-phenanthroline-6-yl, 2,7 -Phenanthroline-8-yl, 2,7-phenanthroline-9-yl, 2,7-phenanthroline-10-yl, 1-phenazinyl, 2-phenazinyl, 1-phenothiazine Base, 2-phenothiazinyl, 3-phenothiazinyl, 4-phenothiazinyl, 1-phenoxazinyl, 2-phenoxazinyl, 3-phenoxazinyl, 4-phenoxazinyl , 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-benzothienyl, 3-benzothienyl, 4-benzothienyl, 5-benzothienyl, 6-benzothienyl, 7-benzothienyl, 1-isobenzothienyl, 3-isobenzothienyl, 4-isobenzothienyl, 5-isobenzothienyl, 6-isobenzothienyl, 7-isobenzothienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2-tert-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl Base-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl Indolyl, 4-tert-butyl-1-indolyl, 2-tert-butyl-3-indolyl or 4-tert-butyl-3-indolyl.
所述Ar中具有6至28个芳族环原子的未取代或取代的芳基为未取代或取代的下述基团：苯基、联苯基、三联苯基、萘基、蒽基、菲基、芘基、并四苯基、芴基、荧蒽基、苯并荧蒽基、二苯并荧蒽基、醋菲烯基、醋蒽烯基、苯并菲基、醋萘并苯并菲基、苝基、苉基、戊芬基、并五苯基、亚四苯基、联三萘基、苯并菲基、二苯并并四苯基、苯并蒽基、二苯并蒽基、苯并四苯基、萘并芘基、苯并芘基、二苯并芘基、苯并辛因基、蒽并四苯基或醋蒽并荧蒽基；The unsubstituted or substituted aryl group having 6 to 28 aromatic ring atoms in the Ar is an unsubstituted or substituted following group: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrene Base, pyrenyl, naphthacene, fluorenyl, fluoranthene, benzofluoranthenyl, dibenzofluoranthenyl, acephenenthrenyl, acethracenyl, triphenanthryl, acenaphthobenzobenzo Phenanthryl, perylene, perylenyl, pentafenyl, pentaphenylene, tetraphenylene, ternaphthyl, triphenylene, dibenzotetraphenyl, benzanthracenyl, dibenzoanthracene benzopyrenyl, benzopyrenyl, naphthopyrenyl, benzopyrenyl, dibenzopyrenyl, benzooctyl, anthracetraphenyl or acethrafluoranthenyl;
所述Ar中具有5至21个芳族环原子的未取代或取代的杂芳基为未取代或取代的下述基团：噻吩基、苯并噻吩基、苯并呋喃基、异苯并呋喃基、吲哚基、异吲哚基、苯并咪唑基、苯并噻唑基、噁唑基、苯并噁唑基、噁二唑基、吡啶基、嘧啶基、吡嗪基、喹啉基、苯并喹啉基、二苯并喹啉基、异喹啉基、苯并异喹啉基、喹唑啉基、喹喔啉基、吖啶基、菲啶基、吩嗪基、吩噁嗪基、咔唑基、4-（N,N’-二苯基胺基）苯基、4-（9H-9-咔唑基）苯基或3-（9H-9-咔唑基）苯基；The unsubstituted or substituted heteroaryl group having 5 to 21 aromatic ring atoms in Ar is an unsubstituted or substituted following group: thienyl, benzothienyl, benzofuryl, isobenzofuran Base, indolyl, isoindolyl, benzimidazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, oxadiazolyl, pyridyl, pyrimidinyl, pyrazinyl, quinolinyl, Benzoquinolinyl, dibenzoquinolinyl, isoquinolinyl, benzisoquinolinyl, quinazolinyl, quinoxalinyl, acridinyl, phenanthridinyl, phenazinyl, phenoxazine yl, carbazolyl, 4-(N,N'-diphenylamino)phenyl, 4-(9H-9-carbazolyl)phenyl or 3-(9H-9-carbazolyl)phenyl ;
所述取代的芳基或取代的杂环芳基的取代基是卤素原子、C1-20的烷基或C1-20的烷氧基。The substituent of the substituted aryl group or substituted heterocyclic aryl group is a halogen atom, a C 1-20 alkyl group or a C 1-20 alkoxy group.
优选地，所述化合物为下述式（I1-I24）中的任意一种：Preferably, the compound is any one of the following formulas (I1-I24):
为解决上述第二个技术问题，本发明采用的技术方案包括如下步骤：In order to solve the above-mentioned second technical problem, the technical solution adopted in the present invention comprises the following steps:
(1)所述式(Ⅰ)化合物由式(X1)化合物在催化剂存在的条件下和式(X2)化合物于混合溶剂中反应，反应产物用二氯甲烷萃取；(1) The compound of formula (I) is reacted with the compound of formula (X2) in a mixed solvent by the compound of formula (X1) in the presence of a catalyst, and the reaction product is extracted with dichloromethane;
(2)干燥步骤(1)制得的萃取液，减压蒸馏得蒸馏液；(2) the extract obtained in the drying step (1), is distilled under reduced pressure to obtain the distillate;
(3)步骤(2)所得蒸馏液经柱层析提纯或经重结晶提纯得式(Ⅰ)化合物。(3) The distillate obtained in step (2) is purified by column chromatography or recrystallized to obtain the compound of formula (I).
优选地，步骤(1)所述催化剂为零价钯，优选四（三苯基）磷钯。Preferably, the catalyst in step (1) is zero-valent palladium, preferably tetrakis(triphenyl)phosphopalladium.
优选地，步骤(1)所述反应在回流状态下进行，温度为80-110℃，时间5-18h。Preferably, the reaction in step (1) is carried out under reflux at a temperature of 80-110° C. for 5-18 hours.
优选地，步骤(1)所述混合溶剂包括A溶剂和B溶剂，所述A溶剂选自碳酸钠水溶液、碳酸钾水溶液、氢氧化钠水溶液和氢氧化钠水溶液中的一种或几种，所述B溶剂选自二氯甲烷、三氯甲烷、二甲基亚砜、N,N-二甲基甲酰胺、1，2-二氯乙烷、甲醇、乙醇、乙醚、乙腈、丙酮、苯和甲苯中的一种或几种。Preferably, the mixed solvent described in step (1) includes A solvent and B solvent, and the A solvent is selected from one or more of sodium carbonate aqueous solution, potassium carbonate aqueous solution, sodium hydroxide aqueous solution and sodium hydroxide aqueous solution, so Said B solvent is selected from dichloromethane, chloroform, dimethyl sulfoxide, N,N-dimethylformamide, 1,2-dichloroethane, methanol, ethanol, ether, acetonitrile, acetone, benzene and One or more of toluene.
为解决上述第三个技术问题，本发明采用的技术方案是提供所述1,3,5-三嗪衍生物在制备白光有机电致发光器件中的应用。In order to solve the third technical problem above, the technical solution adopted in the present invention is to provide the application of the 1,3,5-triazine derivatives in the preparation of white light organic electroluminescent devices.
所述白光有机电致发光二极管的结构为：基片/阳极/空穴传输层/蓝色荧光材料/主体材料：绿色磷光材料/主体材料：红色磷光材料/蓝色荧光材料/电子传输层/阴极，其中，所述蓝色荧光材料和主体材料为同一种所述有机电致发光材料。The structure of the white organic electroluminescent diode is: substrate/anode/hole transport layer/blue fluorescent material/host material: green phosphorescent material/host material: red phosphorescent material/blue fluorescent material/electron transport layer/ A cathode, wherein the blue fluorescent material and the host material are the same organic electroluminescent material.
所述白光有机电致发光器件可按下述方法制备：The white light organic electroluminescent device can be prepared according to the following method:
(1)用清洗剂、去离子水多次清洗带有阳极的玻璃基片；(1) repeatedly cleaning the glass substrate with the anode with cleaning agent and deionized water;
(2)通过真空蒸发的方法蒸镀器件的空穴传输层；(2) Evaporating the hole transport layer of the device by vacuum evaporation;
(3)继续蒸镀本发明中的1,3,5-三嗪衍生物形成蓝色发光层；(3) continue to evaporate the 1,3,5-triazine derivatives in the present invention to form a blue light-emitting layer;
(4)再继续蒸镀包含本发明的1,3,5-三嗪衍生物和绿色磷光材料形成绿色发光层；(4) continue vapor deposition comprising 1,3,5-triazine derivatives of the present invention and green phosphorescent materials to form a green light-emitting layer;
(5)再继续蒸镀包含本发明的1,3,5-三嗪衍生物和红色磷光材料形成红色发光层；(5) continue vapor deposition comprising 1,3,5-triazine derivatives of the present invention and red phosphorescent materials to form a red light-emitting layer;
(6)再继续蒸镀本发明中的1,3,5-三嗪衍生物形成蓝色发光层；(6) Continue to evaporate the 1,3,5-triazine derivatives in the present invention to form a blue light-emitting layer;
(7)继续蒸镀器件的电子传输层；(7) Continue to evaporate the electron transport layer of the device;
(8)再通过蒸镀或溅射的方法制备金属阴极。(8) Prepare a metal cathode by evaporation or sputtering.
所述白光有机电致发光器件中的各层材料为：The materials of each layer in the white light organic electroluminescent device are:
基片是透明的，可以是玻璃或是柔性基片，柔性基片采用聚酯类或聚酞亚胺类化合物中的一种材料。The substrate is transparent and can be glass or a flexible substrate, and the flexible substrate is made of a material among polyester or polyimide compounds.
阳极层可以采用无机材料或有机导电聚合物；无机材料一般为氧化铟锡(以下简称ITO)、氧化锌、氧化锡锌等金属氧化物或金、铜、银等功函数较高的金属，最优化的选择为ITO；有机导电聚合物优选为聚噻吩/聚乙烯基苯磺酸钠(以下简称PEDOT:PSS)和聚苯胺(以下简称PANI)中的任意一种材料。The anode layer can be made of inorganic materials or organic conductive polymers; inorganic materials are generally metal oxides such as indium tin oxide (hereinafter referred to as ITO), zinc oxide, tin zinc oxide, or metals with high work functions such as gold, copper, and silver. The optimal choice is ITO; the organic conductive polymer is preferably any one of polythiophene/sodium polyvinylbenzenesulfonate (hereinafter referred to as PEDOT:PSS) and polyaniline (hereinafter referred to as PANI).
阴极层一般采用锂、镁、钙、锶、铝或铟等功函数较低的金属，或它们中的任一种与铜、金或银的合金，或上述功函数较低的金属或所述合金与金属氟化物交替形成的电极层，本发明优选为Mg:Ag合金层。The cathode layer generally adopts metals with lower work functions such as lithium, magnesium, calcium, strontium, aluminum or indium, or alloys of any of them with copper, gold or silver, or the metals with lower work functions mentioned above or the metals described above. The electrode layers formed alternately by alloys and metal fluorides are preferably Mg:Ag alloy layers in the present invention.
空穴传输层一般采用三芳胺类材料，本发明优选为N,N’-二-(1-萘基)-N,N'-二苯基-1,1-联苯基-4,4-二胺(NPB)、4,4',4''-三(咔唑-9-基)三苯胺(TCTA)。The hole transport layer generally uses triarylamine materials, and the present invention is preferably N,N'-di-(1-naphthyl)-N,N'-diphenyl-1,1-biphenyl-4,4- Diamine (NPB), 4,4',4''-tris(carbazol-9-yl)triphenylamine (TCTA).
电子传输层一般为金属有机配合物，如三(8-羟基喹啉)铝、三（8-羟基喹啉）镓、(水杨醛缩邻胺苯酚)-(8-羟基喹啉)合镓(III)(以下分别简称Alq3,Gaq3,Ga(Saph-q))，也可为邻菲咯琳类，如4,7-二苯基-1,10-邻菲咯琳(以下简称Bphen)等，或苯并咪唑类，如1,3,5-三(1-苯基-1H-苯并咪唑-2-基)苯（TBPI）等；本发明中电子传输材料优选1,3,5-三(1-苯基-1H-苯并咪唑-2-基)苯（TPBI）。The electron transport layer is generally a metal-organic complex, such as tris(8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, (salicylaldehyde o-aminophenol)-(8-hydroxyquinoline)gallium (III) (hereinafter referred to as Alq 3 , Gaq 3 , Ga(Saph-q) respectively), can also be o-phenanthrolines, such as 4,7-diphenyl-1,10-o-phenanthroline (hereinafter referred to as Bphen) etc., or benzimidazoles, such as 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TBPI) etc.; electron transport materials in the present invention are preferably 1,3 , 5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBI).
红色磷光材料、绿色磷光材料是基于Ir、Pt、Ru、Os、Eu、Re、Au和Cu的金属配合物发光材料；Red phosphorescent materials and green phosphorescent materials are metal complex luminescent materials based on Ir, Pt, Ru, Os, Eu, Re, Au and Cu;
所述红色磷光材料选自八乙基卟吩铂[PtOEP]、双(2-(2'-苯并噻吩基)吡啶-N,C3')(乙酰丙酮)合铱[(btp)2Ir(acac)]、二[2-(5-三甲基硅烷噻吩-2-基)-吡啶]合铂[Pt(thpy-SiMe3)]、三(1-苯基-异喹啉)合铱[Ir(piq)3]、双[2-(2-苯并噻唑基-KN3)苯基-KC](2,4-戊二酮酸-KO,KO')铱[(BT)2Ir(acac)]、双(1-苯基异喹啉基)乙酰丙酮代物[Ir(piq)2(acac)]系列材料；The red phosphorescent material is selected from platinum octaethylporphine [PtOEP], bis(2-(2'-benzothienyl)pyridine-N,C3')(acetylacetonate)iridium [(btp) 2 Ir( acac)], bis[2-(5-trimethylsilylthiophen-2-yl)-pyridine]platinum [Pt(thpy-SiMe 3 )], tris(1-phenyl-isoquinoline)iridium[ Ir(piq) 3 ], bis[2-(2-benzothiazolyl-KN3)phenyl-KC](2,4-pentanedione-KO,KO')iridium[(BT) 2 Ir(acac )], bis(1-phenylisoquinolinyl) acetylacetonate [Ir(piq) 2 (acac)] series materials;
所述绿色磷光材料选自三(2-苯基吡啶)合铱[Ir(ppy)3]、乙酰丙酮酸二(2-苯基吡啶)铱[Ir(ppy)2(acac)]、乙酰丙酮酸二(2-苯基苯并咪唑)铱[(pbi)2Ir(acac)]系列材料；The green phosphorescent material is selected from the group consisting of tris(2-phenylpyridine) iridium [Ir(ppy) 3 ], bis(2-phenylpyridine) iridium acetylacetonate [Ir(ppy) 2 (acac)], acetylacetone Acid bis(2-phenylbenzimidazole) iridium [(pbi) 2 Ir(acac)] series materials;
主体材料选自本发明的1,3,5-三嗪类衍生物。The host material is selected from the 1,3,5-triazine derivatives of the present invention.
本发明的有益效果是:The beneficial effects of the present invention are:
该材料自身具有高效蓝色荧光发光，具有较好的色纯度、荧光量子产率和电致发光效率，有较好的成膜性能和热稳定性能，并且材料容易修饰，结构形式多样。The material itself has high-efficiency blue fluorescent light, good color purity, fluorescent quantum yield and electroluminescent efficiency, good film-forming performance and thermal stability, and the material is easy to modify and has various structural forms.
该材料具有较高的三重态能级（高于2.4eV），可同时敏化绿色、红色磷光掺杂材料。应用到器件中，可以利用此材料自身的单重态蓝色荧光发光，以及从该材料传递三重态能量至绿光和红光磷光材料，组合三基色发光得到高效的白光器件。该材料可作为发光材料，也可作为敏化磷光分子的主体材料，由它制作的白光器件比2006年nature期刊上发表的荧光/磷光组合机制的白光器件(Yiru Sun,Mark E.Thompson,Stephen R.Forrest,Managementof singlet and triplet excitons for efficient white organic light-emitting devices,Nature440,908-912)的结构更简化，制作工艺更加简单，成本更低。The material has a high triplet energy level (higher than 2.4eV), which can simultaneously sensitize green and red phosphorescent dopant materials. When applied to a device, the singlet blue fluorescent light of the material itself can be used, and the triplet energy can be transferred from the material to the green and red phosphorescent materials, and a highly efficient white light device can be obtained by combining three primary colors of light. The material can be used as a luminescent material, and can also be used as a host material for sensitized phosphorescent molecules. The white light device made by it is better than the white light device of the fluorescence/phosphorescence combination mechanism published in the journal Nature in 2006 (Yiru Sun, Mark E. Thompson, Stephen R. Forrest, Management of singlet and triplet excitons for efficient white organic light-emitting devices, Nature 440, 908-912) has a simpler structure, simpler manufacturing process and lower cost.
具体实施方式Detailed ways
结合实施例对本发明进一步加以说明。The present invention is further described in conjunction with embodiment.
实施例1Example 1
化合物I1的合成路线如下：The synthetic route of compound I1 is as follows:
化合物I1的合成：将0.240g2-氯-4,6-二苯基-1,3,5-三嗪，0.287g4-(9H-9-咔唑基)苯基硼酸，0.116g四（三苯基膦钯）,浓度为2mol/L的碳酸钠溶液6mL,甲苯8mL和乙醇（分析纯）4mL于90℃和氮气保护条件下加热搅拌12h。反应液经氯仿提取、水洗和无水硫酸钠干燥后，减压蒸干溶剂得到粗产物。将该粗产物进行硅胶柱分离，所用洗脱液为二氯甲烷与石油醚体积比1：4的混合液，真空烘箱中干燥后得到0.309g白色固体I1，产率为65%。Synthesis of compound I1: 0.240g 2-chloro-4,6-diphenyl-1,3,5-triazine, 0.287g4-(9H-9-carbazolyl)phenylboronic acid, 0.116g tetrakis(triphenyl) phosphine palladium), 6mL of sodium carbonate solution with a concentration of 2mol/L, 8mL of toluene and 4mL of ethanol (analytical grade) were heated and stirred at 90°C for 12h under nitrogen protection. After the reaction solution was extracted with chloroform, washed with water and dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was separated on a silica gel column. The eluent used was a mixture of dichloromethane and petroleum ether at a volume ratio of 1:4. After drying in a vacuum oven, 0.309 g of white solid I1 was obtained with a yield of 65%.
产物I1的MS（m/e）：475，对应于：C33H22N4=475；1H NMR(400MHz,CDCl3)δ9.03(d,J=8.5Hz,2H),8.82(dd,J=11.6,10.0Hz,4H),8.18(d,J=7.7Hz,2H),7.83(d,J=8.5Hz,2H),7.70–7.53(m,8H),7.46(t,J=7.3Hz,2H),7.34(t,J=7.3Hz,2H)。证明该化合物是I1。MS (m/e) of product I1: 475, corresponding to: C33H22N4=475; 1 H NMR (400MHz, CDCl 3 ) δ9.03(d, J=8.5Hz, 2H), 8.82(dd, J=11.6, 10.0Hz, 4H), 8.18(d, J=7.7Hz, 2H), 7.83(d, J=8.5Hz, 2H), 7.70–7.53(m, 8H), 7.46(t, J=7.3Hz, 2H) ,7.34(t,J=7.3Hz,2H). It turns out that the compound is I1.
实施例2Example 2
化合物I2的合成路线如下：The synthetic route of compound I2 is as follows:
化合物I2的合成：将0.900g2-氯-4,6-二苯氧基-1,3,5-三嗪，0.867g4-(9H-9-咔唑基)苯基硼酸，0.346g四（三苯基膦钯）,浓度为2mol/L的碳酸钠溶液9mL,甲苯（分析纯）12mL和乙醇（分析纯）6mL于45℃和氮气保护条件下加热搅拌10h。反应液经氯仿提取、水洗和无水硫酸钠干燥后，减压蒸干溶剂得到粗产物。将该粗产物进行硅胶柱分离，所用洗脱液为二氯甲烷与石油醚体积比1:3的混合液，真空烘箱中干燥后得到1.214g白色固体I2，产率为80%。Synthesis of compound I2: 0.900g 2-chloro-4,6-diphenoxy-1,3,5-triazine, 0.867g4-(9H-9-carbazolyl)phenylboronic acid, 0.346g tetrakis(tri Phenylphosphine palladium), 9 mL of sodium carbonate solution with a concentration of 2 mol/L, 12 mL of toluene (analytical pure) and 6 mL of ethanol (analytical pure) were heated and stirred at 45 °C for 10 h under nitrogen protection. After the reaction solution was extracted with chloroform, washed with water and dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was separated on a silica gel column, and the eluent used was a mixture of dichloromethane and petroleum ether at a volume ratio of 1:3. After drying in a vacuum oven, 1.214 g of white solid I2 was obtained, with a yield of 80%.
产物I2的MS（m/e）：506，对应于：C33H22N4O2=506；1H NMR(400MHz,CDCl3)δ8.52(d,J=8.5Hz,2H),8.14(d,J=7.7Hz,2H),7.67(d,J=8.4Hz,2H),7.49-7.40(m,8H),7.33-7.28(m,8H)。证明该化合物是I2。MS (m/e) of product I2: 506, corresponding to: C33H22N4O2=506; 1 H NMR (400MHz, CDCl 3 ) δ8.52(d, J=8.5Hz, 2H), 8.14(d, J=7.7Hz ,2H),7.67(d,J=8.4Hz,2H),7.49-7.40(m,8H),7.33-7.28(m,8H). It turns out that the compound is I2.
实施例3Example 3
化合物I3的合成路线如下：The synthetic route of compound I3 is as follows:
化合物I3的合成：将0.240g2-氯-4,6-二苯基-1,3,5-三嗪，0.280g4-硼酸三苯胺，0.116g四（三苯基膦钯）,浓度为2mol/L的碳酸钠溶液6mL,甲苯（分析纯）8mL和乙醇（分析纯）4mL于90℃和氮气保护条件下加热搅拌12h。反应液经氯仿提取、水洗和无水硫酸钠干燥后，减压蒸干溶剂得到粗产物。将该粗产物进行硅胶柱分离，所用洗脱液为二氯甲烷与石油醚体积比1：4的混合液，真空烘箱中干燥后得到0.350g淡黄色固体I3，产率为74%。Synthesis of compound I3: 0.240g 2-chloro-4,6-diphenyl-1,3,5-triazine, 0.280g 4-triphenylamine borate, 0.116g tetrakis(triphenylphosphine palladium), the concentration is 2mol/ 6 mL of sodium carbonate solution in L, 8 mL of toluene (analytical pure) and 4 mL of ethanol (analytical pure) were heated and stirred at 90 ° C for 12 h under nitrogen protection. After the reaction solution was extracted with chloroform, washed with water and dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was separated on a silica gel column, and the eluent used was a mixture of dichloromethane and petroleum ether at a volume ratio of 1:4. After drying in a vacuum oven, 0.350 g of light yellow solid I3 was obtained, with a yield of 74%.
产物I3的MS（m/e）：476，对应于：C33H24N4=476；1H NMR(400MHz,CDCl3)δ8.75(dd,J=7.9,1.4Hz,4H),8.61(d,J=8.8Hz,2H),7.65–7.50(m,6H),7.33(t,J=7.8Hz,4H),7.24–7.08(m,8H)。证明该化合物是I3。MS (m/e) of product I3: 476, corresponding to: C33H24N4=476; 1 H NMR (400MHz, CDCl 3 ) δ8.75(dd, J=7.9, 1.4Hz, 4H), 8.61(d, J= 8.8Hz, 2H), 7.65–7.50(m, 6H), 7.33(t, J=7.8Hz, 4H), 7.24–7.08(m, 8H). The compound was proved to be I3.
实施例4Example 4
化合物I6的合成路线如下：The synthetic route of compound I6 is as follows:
化合物I6的合成：将0.900g2-氯-4,6-二苯氧基-1,3,5-三嗪，1.089g4’-(9H-9-咔唑基)联苯基-4-硼酸，0.346g四（三苯基膦钯）,浓度为2mol/L的碳酸钠溶液9mL,甲苯（分析纯）12mL和乙醇（分析纯）6mL于90℃和氮气保护条件下加热搅拌15h。反应液经氯仿提取、水洗和无水硫酸钠干燥后，减压蒸干溶剂得到粗产物。将该粗产物进行硅胶柱分离，所用洗脱液为二氯甲烷与石油醚体积比1:3的混合液，真空烘箱中干燥后得到1.048g白色固体I6，产率为60%。Synthesis of compound I6: 0.900g 2-chloro-4,6-diphenoxy-1,3,5-triazine, 1.089g 4'-(9H-9-carbazolyl)biphenyl-4-boronic acid, 0.346g of tetrakis(triphenylphosphine palladium), 9mL of sodium carbonate solution with a concentration of 2mol/L, 12mL of toluene (analytical pure) and 6mL of ethanol (analytical pure) were heated and stirred at 90°C for 15h under nitrogen protection. After the reaction solution was extracted with chloroform, washed with water and dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was subjected to silica gel column separation, and the eluent used was a mixture of dichloromethane and petroleum ether at a volume ratio of 1:3. After drying in a vacuum oven, 1.048 g of white solid I6 was obtained, with a yield of 60%.
产物I6的MS（m/e）：582，对应于：C39H26N4O2=506；1H NMR(400MHz,CDCl3)δ8.43(d,J=8.4Hz,2H),8.16(d,J=7.7Hz,2H),7.87(d,J=8.4Hz,2H),7.76(d,J=8.3Hz,2H),7.68(d,J=8.4Hz,2H),7.53–7.39(m,8H),7.35–7.27(m,8H)。证明该化合物是I6。MS (m/e) of product I6: 582, corresponding to: C39H26N4O2=506; 1 H NMR (400MHz, CDCl 3 ) δ8.43(d, J=8.4Hz, 2H), 8.16(d, J=7.7Hz ,2H),7.87(d,J=8.4Hz,2H),7.76(d,J=8.3Hz,2H),7.68(d,J=8.4Hz,2H),7.53–7.39(m,8H),7.35 –7.27(m,8H). The compound was proved to be I6.
实施例5Example 5
以本发明提供的1,3,5-三嗪衍生物作为发光层的主体材料制备WOLEDs器件及其性能测定：Preparation of WOLEDs device and its performance measurement using the 1,3,5-triazine derivative provided by the invention as the host material of the light-emitting layer:
WOLEDs器件的典型结构为:基片/阳极/空穴传输层(HTL)/蓝色荧光材料/主体材料：绿色磷光材料/主体材料：红色磷光材料/蓝色荧光材料/电子传输层（ETL）/阴极。The typical structure of WOLEDs device is: substrate/anode/hole transport layer (HTL)/blue fluorescent material/host material: green phosphorescent material/host material: red phosphorescent material/blue fluorescent material/electron transport layer (ETL) /cathode.
WOLEDs器件的制备：Preparation of WOLEDs devices:
将涂布了氧化铟锡（ITO）透明导电层的玻璃板在商用清洗剂中超声处理；用去离子水冲洗后，在丙酮:乙醇混合溶剂中超声除油；在洁净环境下烘烤至完全除去水份，用紫外光清洗机照射20分钟。The glass plate coated with indium tin oxide (ITO) transparent conductive layer is ultrasonically treated in a commercial cleaning agent; after rinsing with deionized water, ultrasonically degrease in acetone:ethanol mixed solvent; bake in a clean environment until completely Remove moisture, and irradiate with ultraviolet light cleaning machine for 20 minutes.
将上述清洗好的带有阳极的玻璃基片置于真空腔内，抽真空至1×10-5～9×10-3Pa，在上述空穴注入层膜上蒸镀N,N’-二苯基-N,N’-(1-萘基)-1,1’-联苯-4,4’-二胺（NPB）作为空穴传输层，蒸镀速率为0.1nm/s，蒸镀膜厚为10-40nm。Place the above cleaned glass substrate with anode in a vacuum chamber, evacuate to 1×10 -5 ~ 9×10 -3 Pa, evaporate N,N'-Di Phenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB) is used as the hole transport layer, the evaporation rate is 0.1nm/s, and the evaporation film The thickness is 10-40nm.
在空穴传输层之上，继续蒸镀一层本发明提供的1,3,5-三嗪衍生物作为器件的蓝色发光层，蒸镀速率为0.1nm/s，蒸镀膜厚为10-30nm；继续蒸镀一层掺杂有绿色磷光材料如三(2-苯基吡啶)合铱[Ir(ppy)3]的1,3,5-三嗪衍生物作为器件的绿色发光层，绿色磷光材料在1,3,5-三嗪衍生物中的掺杂浓度为1-20wt%，蒸镀速率为0.1nm/s，蒸镀膜厚为10-30nm；继续蒸镀一层掺杂有红色磷光材料如三(1-苯基-异喹啉)合铱[Ir(piq)3]的1,3,5-三嗪衍生物作为器件的红色发光层，红色磷光材料在1,3,5-三嗪衍生物中的掺杂浓度为1-20wt%，蒸镀速率为0.1nm/s，蒸镀膜厚为10-30nm；继续蒸镀一层1,3,5-三嗪衍生物作为器件的蓝色发光层，蒸镀速率为0.1nm/s，蒸镀膜厚为10-30nm。On the hole transport layer, continue to evaporate a layer of 1,3,5-triazine derivatives provided by the present invention as the blue light-emitting layer of the device, the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10- 30nm; continue to vapor-deposit a layer of 1,3,5-triazine derivatives doped with green phosphorescent materials such as tris(2-phenylpyridine) iridium [Ir(ppy)3] as the green light-emitting layer of the device, green The doping concentration of the phosphorescent material in the 1,3,5-triazine derivative is 1-20wt%, the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10-30nm; continue to evaporate a layer doped with red Phosphorescent materials such as 1,3,5-triazine derivatives of tris(1-phenyl-isoquinoline)iridium [Ir(piq)3] are used as the red light-emitting layer of the device, and the red phosphorescent materials are at 1,3,5 -The doping concentration in the triazine derivative is 1-20wt%, the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10-30nm; continue to evaporate a layer of 1,3,5-triazine derivative as a device The blue light-emitting layer, the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10-30nm.
再继续蒸镀一层1,3,5-三(1-苯基-1H-苯并咪唑-2-基)苯(TPBI)作为器件的电子传输层，其蒸镀速率为0.lnm/s，蒸镀总膜厚为10-40nm。Continue to evaporate one deck 1,3,5-three (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBI) as the electron transport layer of device, and its evaporation rate is 0.1nm/s , the total film thickness of evaporation is 10-40nm.
最后，在上述电子传输层之上蒸镀镁:银合金层作为器件的阴极层，镁:银合金层的蒸镀速率为2.0～3.Onm/s，厚度为50-200nm。Finally, a magnesium:silver alloy layer is vapor-deposited on the above-mentioned electron transport layer as the cathode layer of the device, the vapor deposition rate of the magnesium:silver alloy layer is 2.0-3.0nm/s, and the thickness is 50-200nm.
本发明中用的几种材料的结构式如下：The structural formulas of several materials used in the present invention are as follows:
实施例6：Embodiment 6:
以化合物I1作为蓝色荧光材料兼主体材料时，所得到的F/P-WOLED器件结构如下：When compound I1 is used as the blue fluorescent material and host material, the obtained F/P-WOLED device structure is as follows:
ITO/PEDOT/NPB(30nm)/I1(15nm)/I1:5%Ir(ppy)3(10nm)/I1:5%Ir(piq)3(10nm)/I1(15nm)/TPBI(30nm)/Mg:AgITO/PEDOT/NPB(30nm)/I1(15nm)/I1:5%Ir(ppy) 3 (10nm)/I1:5%Ir(piq) 3 (10nm)/I1(15nm)/TPBI(30nm)/ Mg:Ag
器件性能指标如下：The device performance indicators are as follows:
CIE值：(0.37,0.39)，器件色纯度在很大范围内不受工作电压影响。CIE value: (0.37,0.39), the color purity of the device is not affected by the working voltage in a wide range.
开启电压：3.8VTurn on voltage: 3.8V
最大亮度：7500cd/m2 Maximum brightness: 7500cd/m 2
最大电流效率：20.6cd/AMaximum current efficiency: 20.6cd/A
实施例7Example 7
以化合物I2作为蓝色荧光材料兼主体材料时，所得到的F/P-WOLED器件结构如下：When compound I2 is used as the blue fluorescent material and host material, the obtained F/P-WOLED device structure is as follows:
ITO/PEDOT/NPB(15nm)/I2(15nm)/I2:5%Ir(ppy)3(10nm)/I2:5%Ir(piq)3(10nm)/I2(15nm)/TPBI(30nm)/Mg:AgITO/PEDOT/NPB(15nm)/I2(15nm)/I2:5%Ir(ppy) 3 (10nm)/I2:5%Ir(piq) 3 (10nm)/I2(15nm)/TPBI(30nm)/ Mg:Ag
器件性能指标如下：The device performance indicators are as follows:
CIE值：(0.40,0.43)，器件色纯度在很大范围内不受工作电压影响。CIE value: (0.40,0.43), the color purity of the device is not affected by the working voltage in a wide range.
开启电压：3.5VTurn on voltage: 3.5V
最大亮度：10500cd/m2 Maximum brightness: 10500cd/ m2
最大电流效率：26.5cd/AMaximum current efficiency: 26.5cd/A
实施例8Example 8
以化合物I3作为蓝色荧光材料兼主体材料时，所得到的F/P-WOLED器件结构如下：When compound I3 is used as the blue fluorescent material and host material, the obtained F/P-WOLED device structure is as follows:
ITO/PEDOT/NPB(15nm)/I3(15nm)/I3:5%Ir(ppy)3(10nm)/I3:5%Ir(piq)3(10nm)/I3(15nm)/TPBI(30nm)/Mg:AgITO/PEDOT/NPB(15nm)/I3(15nm)/I3:5%Ir(ppy) 3 (10nm)/I3:5%Ir(piq) 3 (10nm)/I3(15nm)/TPBI(30nm)/ Mg:Ag
器件性能指标如下：The device performance indicators are as follows:
CIE值：(0.40,0.38)，器件色纯度在很大范围内不受工作电压影响。CIE value: (0.40,0.38), the color purity of the device is not affected by the working voltage in a wide range.
开启电压：3.0VTurn on voltage: 3.0V
最大亮度：11500cd/m2 Maximum brightness: 11500cd/m 2
最大电流效率：23.5cd/AMaximum current efficiency: 23.5cd/A
实施例9Example 9
以化合物I6作为蓝色荧光材料兼主体材料时，所得到的F/P-WOLED器件结构如下：When compound I6 is used as the blue fluorescent material and host material, the obtained F/P-WOLED device structure is as follows:
ITO/PEDOT/NPB(15nm)/I6(15nm)/I6:5%Ir(ppy)3(10nm)/I6:5%Ir(piq)3(10nm)/I6(15nm)/TPBI(30nm)/Mg:AgITO/PEDOT/NPB(15nm)/I6(15nm)/I6:5%Ir(ppy) 3 (10nm)/I6:5%Ir(piq) 3 (10nm)/I6(15nm)/TPBI(30nm)/ Mg:Ag
器件性能指标如下：The device performance indicators are as follows:
CIE值：(0.36,0.44)，器件色纯度在很大范围内不受工作电压影响。CIE value: (0.36,0.44), the color purity of the device is not affected by the working voltage in a wide range.
开启电压：4.2VTurn on voltage: 4.2V
最大亮度：5300cd/m2 Maximum brightness: 5300cd/ m2
最大电流效率：15.1cd/AMaximum current efficiency: 15.1cd/A
以上所列出的F/P-WOLED器件均能够用于有机晶体管、有机集成电路、有机太阳能电池、有机激光器或者有机传感器中。All the F/P-WOLED devices listed above can be used in organic transistors, organic integrated circuits, organic solar cells, organic lasers or organic sensors.
尽管结合优选实施例对本发明进行了说明，但本发明并不局限于上述实施例，应当理解，在本发明构思的引导下，本领域技术人员可进行各种修改和改进。Although the present invention has been described in conjunction with preferred embodiments, the present invention is not limited to the above embodiments. It should be understood that under the guidance of the concept of the present invention, those skilled in the art can make various modifications and improvements.
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