CN115677594A - Pyrimidine derivative and preparation method and application thereof - Google Patents
Pyrimidine derivative and preparation method and application thereof Download PDFInfo
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- CN115677594A CN115677594A CN202211103134.7A CN202211103134A CN115677594A CN 115677594 A CN115677594 A CN 115677594A CN 202211103134 A CN202211103134 A CN 202211103134A CN 115677594 A CN115677594 A CN 115677594A
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- 150000003230 pyrimidines Chemical class 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title abstract description 9
- 239000000463 material Substances 0.000 claims abstract description 29
- 239000010410 layer Substances 0.000 claims description 76
- -1 Alkyl radical Chemical class 0.000 claims description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 239000000243 solution Substances 0.000 claims description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- 238000002347 injection Methods 0.000 claims description 11
- 239000007924 injection Substances 0.000 claims description 11
- 230000005525 hole transport Effects 0.000 claims description 10
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229910052805 deuterium Inorganic materials 0.000 claims description 9
- 239000013067 intermediate product Substances 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 150000005840 aryl radicals Chemical class 0.000 claims description 8
- 230000000903 blocking effect Effects 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 7
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 6
- 239000011259 mixed solution Substances 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 claims description 6
- 238000004440 column chromatography Methods 0.000 claims description 5
- 239000010409 thin film Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000004327 boric acid Substances 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 239000002346 layers by function Substances 0.000 claims description 4
- 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 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000012467 final product Substances 0.000 claims description 3
- 238000005286 illumination Methods 0.000 claims description 3
- 239000012046 mixed solvent Substances 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 3
- 238000000034 method Methods 0.000 description 11
- 238000000151 deposition Methods 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- 230000008569 process Effects 0.000 description 7
- 230000008021 deposition Effects 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- 238000007738 vacuum evaporation Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 150000001491 aromatic compounds Chemical class 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 125000006413 ring segment Chemical group 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 235000009161 Espostoa lanata Nutrition 0.000 description 2
- 240000001624 Espostoa lanata Species 0.000 description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 125000001246 bromo group Chemical group Br* 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
- 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 2
- 230000003111 delayed effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001786 isothiazolyl group Chemical group 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 229910052717 sulfur Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000004589 thienofuryl group Chemical group O1C(=CC2=C1C=CS2)* 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ATTVYRDSOVWELU-UHFFFAOYSA-N 1-diphenylphosphoryl-2-(2-diphenylphosphorylphenoxy)benzene Chemical compound C=1C=CC=CC=1P(C=1C(=CC=CC=1)OC=1C(=CC=CC=1)P(=O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(=O)C1=CC=CC=C1 ATTVYRDSOVWELU-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- 241000194370 Cyclocephala pan Species 0.000 description 1
- 229910016460 CzSi Inorganic materials 0.000 description 1
- 241000359496 Kaistibacter Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- WIHKEPSYODOQJR-UHFFFAOYSA-N [9-(4-tert-butylphenyl)-6-triphenylsilylcarbazol-3-yl]-triphenylsilane Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C2=CC=C([Si](C=3C=CC=CC=3)(C=3C=CC=CC=3)C=3C=CC=CC=3)C=C2C2=CC([Si](C=3C=CC=CC=3)(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=C21 WIHKEPSYODOQJR-UHFFFAOYSA-N 0.000 description 1
- PQGAHNJECSVDEI-UHFFFAOYSA-N [CH2]CCCCC Chemical compound [CH2]CCCCC PQGAHNJECSVDEI-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 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
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- WYEMLYFITZORAB-UHFFFAOYSA-N boscalid Chemical compound C1=CC(Cl)=CC=C1C1=CC=CC=C1NC(=O)C1=CC=CN=C1Cl WYEMLYFITZORAB-UHFFFAOYSA-N 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 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
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
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Abstract
The invention discloses a preparation method and application of a pyrimidine derivative, wherein the pyrimidine derivative has a structure shown as a formula (I); the invention effectively solves the problem that the existing blue light and deep blue light TADF materials and main materials are less by improving the key chemical structure of the pyrimidine derivatives and the like and applying the pyrimidine derivatives as organic electroluminescent layer materials in organic electroluminescent devices.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a pyrimidine derivative and a preparation method and application thereof.
Background
In 1987, c.w.tang et al of Kodak corporation in usa prepared a light emitting device having Indium Tin Oxide (ITO) and a metal alloy thin film as an anode and a cathode, respectively, an aromatic amine based material as a hole transport layer, and an aluminum complex of 8-hydroxyquinoline (Alq 3) as an electron transport layer and a light emitting layer, and having a device efficiency of 1.51lm/W (see c.w.tang and s.a.wanslyke, appl.phys.lett.,1978,51, 913), and since then, research on organic electroluminescence technology has been promoted globally.
According to the constraint of quantum mechanical transition law of electron spin conservation, the traditional fluorescent dye can only utilize 25% of energy of singlet excitons, and the limit of internal quantum efficiency is 25%. Forrest et al, at princeton university in the united states of 1998, used a metal platinum complex phosphorescent material to produce a light emitting device with 23% internal quantum efficiency and 4% external quantum efficiency (see m.a. baldo, d.f. o' Brienetal, nature,1998,395, 151). The spin orbit coupling induced by iridium, platinum and other heavy metals enables triplet excitons to return to the ground state directly through a radiative transition process to emit phosphorescence, and the theoretical internal quantum efficiency can reach 100%. However, the introduction of iridium and platinum and other heavy metals increases the cost of the phosphorescent material, and the deep blue light phosphorescent material has poor chemical stability, so that the efficiency roll-off of the device is severe at high brightness. Therefore, the development of cheap and stable organic small molecule materials to realize efficient and stable OLED devices is urgently needed.
In recent years, a Thermally Activated Delayed Fluorescence (TADF) material can also achieve 100% exciton utilization due to the characteristic that triplet excitons can reverse intersystem crossing process back to singlet state, thereby emitting Delayed Fluorescence (see h.uoyama, k.goushi, k.shizu, h.nomura, c.adachi, nature,2012,492, 234). TADF materials emitting light of blue, green, red, etc. have been developed rapidly in recent years (see t.a. Lin, t.chatterjee, w.l.tsai, w.k.lee, m.j.wu, m.jiao, k.c.pan, c.l.yi, c.l.chung, k.t.wong, and c.c.wu, adv.mater, 2016,28,6976, tien-Lin Wu, min-Jie Huang, chi-Chun Lin, pei-Yun Huang, tsu-Yu Chou, ren-Wu Chen-ng, hao-Wu Lin, rai-shun, and Chien-Hong, chen photo song, 2018,12,235, yasuhiro Kondo, kazuki Yoshiura, sayuri Kitera, hiroki Nishi, susumu Oda, hajime Gotoh, yasuyuki Sasada, motoki Yanai, and Takuji Hatakeyyama, nature Photonics,2019,13,678, J.X.Chen, W.W.Tao, W.C.Chen, Y.F.Xiao, K.Wang, C.Cao, J.Yu, S.Li, F.X.Geng, C.Adachi, C.S.Lee, and X.H.Zhang, angew.Chem.int.Ed.Engl, U.S. 2019,58,14660, J.Xue, Q.Liang, R.Wang, J.Hou, W.Li, Q.Peng, Z.Shuai, and J.Qiao, adv.Mater.,2019,31,1808242, Y.L.Zhang, Q.ran, Q.Wang, Y.Liu, C.Hanisch, S.Reineke, J.Fan, and L.S.Liao, adv.Mater.,2019,31, 1902368). However, because the excited state characteristic of charge transfer in the TADF material molecule makes the spectrum red-shifted, the existing blue light and deep blue light TADF materials are very rare, so that the development of host materials suitable for blue light and deep blue light is also limited, and this also affects the application prospects of high-efficiency TADF materials in full-color display and white light illumination.
Disclosure of Invention
In view of the above-mentioned shortcomings of the prior art, the present invention aims to provide a pyrimidine derivative with TADF characteristics, and a preparation method and application thereof, and aims to solve the problem of less blue light and deep blue light TADF materials and host materials.
In order to achieve the purpose, the invention provides the following technical scheme:
in one aspect, the present invention provides a pyrimidine derivative having a structure represented by the following formula (I):
wherein R is 1 、R 2 Each occurrence is independently C 6 ～C 14 Aryl radicals, substituted by one or more R a Substituted C 6 ～C 14 Aryl, 5-to 18-membered heteroaryl, substituted with one or more R a Substituted 5-to 18-membered heteroaryl;
R a independently at each occurrence, D (deuterium), fluorine, C 1 ～C 12 Alkyl radical, C 1 ～C 12 Alkoxy radical, C 3 ～C 10 Cycloalkyl, or C 6 ～C 14 An aryl group;
R 3 each occurrence is independently C 1 ～C 20 Alkyl radical, C 1 ～C 20 Alkoxy radical, C 3 -C 10 Cycloalkyl radical, C 6 ～C 14 Aryl radicals, substituted by one or more R b Substituted C 6 ～C 14 Aryl, 5-to 18-membered heteroaryl, substituted with one or more R b Substituted 5-to 18-membered heteroaryl, diphenylamino, or substituted with one or more R b A substituted diphenylamine group;
R b independently at each occurrence, D (deuterium), fluorine, C 1 ～C 12 Alkyl, aryl, heteroaryl, and heteroaryl,C 1 ～C 12 Alkoxy radical, C 3 ～C 10 Cycloalkyl radical, C 6 ～C 14 Aryl radicals, substituted by one or more R c Substituted C 6 ～C 14 Aryl, 5-to 18-membered heteroaryl, substituted with one or more R c Substituted 5-to 18-membered heteroaryl, diphenylamino, or substituted with one or more R c A substituted diphenylamine group;
R c independently at each occurrence, D (deuterium), fluorine, C 1 ～C 12 Alkyl radical, C 1 ～C 12 Alkoxy radical, C 3 ～C 10 Cycloalkyl radical, C 6 ～C 14 Aryl, C substituted by one or more Rc 6 ～C 14 Aryl radical, by one or more R d Substituted C 6 ～C 14 Aryl, 5-to 18-membered heteroaryl, substituted with one or more R d Substituted 5-to 18-membered heteroaryl, diphenylamino, or substituted with one or more R d A substituted diphenylamine group;
R d independently at each occurrence, D (deuterium), fluorine, C 1 ～C 12 Alkyl radical, C 1 ～C 12 Alkoxy radical, C 3 ～C 10 Cycloalkyl, or C 6 ～C 14 An aryl group;
the above alkyl, alkoxy, cycloalkyl, aryl, heteroaryl groups are optionally substituted with one or more substituents selected from the group consisting of: halogen, -CN, C1-C12 alkyl, C1-C12 alkoxy, C1-C12 haloalkyl, C2-C6 alkenyl, C3-C10 cycloalkyl, C6-C14 aryl, and 5-to 18-membered heteroaryl.
In another aspect, the present invention also provides an organic electroluminescent material, which comprises the pyrimidine derivatives as described above.
In yet another aspect, the present invention also provides an organic electroluminescent device comprising an anode, a cathode, and an organic thin film layer interposed between the anode and the cathode, the organic thin film layer comprising a light-emitting layer, an optional hole-injecting layer, an optional hole-transporting layer, an optional electron-transporting layer, and an optional electron-injecting layer; wherein at least one of the light-emitting layer, the electron injection layer, the electron transport layer, the hole transport layer and the hole injection layer comprises the pyrimidine derivative.
Further, the organic electroluminescent device further comprises an optional hole blocking layer, an optional electron blocking layer and an optional capping layer.
Furthermore, the organic electroluminescent device also comprises a substrate, and an anode layer, an organic light-emitting functional layer and a cathode layer which are sequentially formed on the substrate; the organic light-emitting functional layer comprises any one or combination of a plurality of light-emitting layers, hole injection layers, hole transport layers, electron blocking layers, hole blocking layers, electron transport layers and electron injection layers, wherein the light-emitting layers comprise the pyrimidine derivatives.
The invention further provides application of the organic electroluminescent device in preparing an organic electroluminescent display or an illumination light source.
In another aspect, the present invention provides a method for preparing the above pyrimidine derivative, comprising the steps of:
dissolving trifluoromethanesulfonic anhydride and a cyano raw material compound (A) in a dry dichloromethane solution, then adding the mixed solution into a dry single-mouth bottle, dropwise adding a dichloromethane solution dissolved with a bromoacetyl compound (B) into the mixed solution, stirring for 24-120 hours at room temperature under the protection of nitrogen, removing the dichloromethane solvent under vacuum reduced pressure after the reaction is finished, and purifying by using column chromatography to obtain an intermediate product (II);
secondly, adding the intermediate product (II), the boric acid compound (C) and potassium carbonate into a double-mouth bottle, then adding a mixed solvent of water and toluene, adding tetrakis (triphenylphosphine) palladium under the condition of nitrogen, performing reflux reaction for 6-24 hours after ventilation, and after the reaction is finished, extracting, performing column chromatography and sublimating to obtain a final product (I)
Compared with the prior art, the invention has the beneficial effects that:
the pyrimidine derivative prepared by the invention has weaker electron-withdrawing ability, can obtain deep blue light and blue light emission (emission wavelength is less than 470 nm) with TADF (TADF) characteristics by combining with a donor unit, and has higher triplet state energy level (not less than 2.70 eV), so that the pyrimidine derivative has bipolar transmission characteristics and can be used as a main body of blue light, green light and red light materials; tests prove that the organic electroluminescent device used by the invention has good efficiency and device service life and has higher application prospect.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the embodiments or the description of the prior art will be briefly described below, and it is obvious that the drawings in the following description are some embodiments of the present invention, and other drawings can be obtained by those skilled in the art without creative efforts.
Fig. 1 shows a schematic structural view of an organic electroluminescent device in an embodiment of the present invention;
FIG. 2 shows a generation spectrum of a dilute solution of compound (Pm-1) in one embodiment of the present invention;
FIG. 3 shows an emission spectrum of a dilute solution of compound (Pm-4) in an embodiment of the present invention;
in the figure: 1. a substrate; 2. an anode; 3. a hole transport layer; 4. a light emitting layer; 5. an electron transport layer; 6. an electron injection layer; 7. a cathode layer;
in FIG. 2, the emission peak is at 455nm; in FIG. 3, the emission peak is at 402nm.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present disclosure more apparent, the technical solutions of the embodiments of the present disclosure will be described clearly and completely with reference to the drawings of the embodiments of the present disclosure. It is to be understood that the described embodiments are only a few embodiments of the present disclosure, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the described embodiments of the disclosure without any inventive step, are within the scope of protection of the invention.
It is to be understood that any and all embodiments of the invention may be used with any and all embodiments of the invention without conflict
The features of one embodiment or of several other embodiments may be combined to yield yet further embodiments. The present invention includes such combinations to yield additional embodiments.
In the present specification, groups and substituents thereof may be selected by one skilled in the art to provide stable moieties and compounds. When a substituent is described by a general formula written from left to right, the substituent also includes chemically equivalent substituents obtained when the formula is written from right to left.
The section headings used in this specification are for organizational purposes only and are not to be construed as limiting the subject matter described. All documents, or portions of documents, cited in this disclosure, including, but not limited to, patents, patent applications, articles, books, operating manuals, and treatises, are hereby incorporated by reference in their entirety.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as is standard in the art to which the claimed subject matter belongs. In case there are multiple definitions for a term, the definitions herein control.
It should be understood that as used herein, singular forms, such as "a", "an", include plural references unless the context clearly dictates otherwise. Furthermore, the term "comprising" is open-ended, i.e. including what is specified in the invention, but not excluding other aspects.
The present invention employs conventional methods of mass spectrometry, elemental analysis, and the steps and conditions may be referred to those conventional in the art, unless otherwise specified.
Unless otherwise indicated, the present invention employs standard nomenclature for analytical chemistry, organic synthetic chemistry, and optics, and standard laboratory procedures and techniques. In some cases, standard techniques are used for chemical synthesis, chemical analysis, light emitting device performance detection.
The compounds of the present invention may contain unnatural proportions of atomic isotopes at one or more of the atoms that constitute such compounds. For example, compounds may be labeled with radioisotopes, such as deuterium (2H). All isotopic variations of the compounds of the present invention, whether radioactive or not, are intended to be encompassed within the scope of the present invention.
In the present invention, the number of said "substitution" may be one or more unless otherwise specified; when plural, it means two or more, for example, 2, 3 or 4. When the number of the "substitution" is plural, the "substitution" may be the same or different. In the present disclosure, the position of "substitution" may be arbitrary unless otherwise specified.
In the present invention, the term "alkyl" as a group or as part of another group (e.g., as used in halogen-substituted alkyl groups and the like) is intended to include both branched and straight chain saturated aliphatic hydrocarbon groups having the indicated number of carbon atoms. E.g. C 1 ～C 20 The alkyl group includes a straight or branched alkyl group having 1 to 20 carbon atoms. As in "C 1 ～C 6 Alkyl is defined to include groups having 1, 2, 3, 4, 5, or 6 carbon atoms in a straight or branched chain configuration. For example, in the present invention, said C 1 ～C 6 Each alkyl group is independently methyl, ethyl, propyl, butyl, pentyl or hexyl; wherein propyl is C 3 Alkyl (including isomers such as n-propyl or isopropyl); butyl being C 4 Alkyl (including isomers such as n-butyl, sec-butyl, isobutyl, or tert-butyl); pentyl is C 5 Alkyl (including isomers such as n-pentyl, 1-methyl-butyl, 1-ethyl-propyl, 2-methyl-1-butyl, 3-methyl-1-butyl, isopentyl, tert-pentyl or neopentyl); hexyl radical is C 6 Alkyl (including isomers such as n-hexyl or isohexyl).
The term "alkoxy" as used herein refers to an alkyl group as defined above, each attached via an oxygen linkage (-O-).
As a group or as part of another group in this disclosureIn general, the term "Cn-m aryl" refers to a monocyclic or polycyclic aromatic group having n to m ring carbon atoms (the ring atoms being only carbon atoms) having at least one carbocyclic ring having a conjugated pi-electron system. Examples of the above aryl unit include a phenyl group, a naphthyl group, an indenyl group, an azulenyl group, a fluorenyl group, a phenanthryl group, or an anthryl group. In one embodiment, the aryl group is preferably C 6 -C 14 Aryl groups such as phenyl and naphthyl, more preferably phenyl.
In the context of the present invention, the term "n-m membered heteroaryl" as a group or part of another group refers to an aromatic group having ring atoms comprising one or more (e.g., 1, 2, 3, and 4) heteroatoms selected from nitrogen, oxygen, and sulfur, the ring atoms of which are n to m, the heteroaryl being a monocyclic, bicyclic, tricyclic, or tetracyclic ring system, wherein at least one ring is aromatic. Heteroaryl groups within the scope of this definition include, but are not limited to: acridinyl, carbazolyl, cinnolinyl, quinoxalinyl, pyrazolyl, indolyl, benzotriazolyl, furyl, thienyl, benzothienyl, benzofuryl, quinolyl, isoquinolyl, oxazolyl, isoxazolyl, pyrazinyl, pyridazinyl, pyridyl, pyrimidinyl, pyrrolyl, tetrahydroquinoline, imidazolyl, triazolyl, tetrazolyl, thiazolyl, isothiazolyl, furazanyl, thiadiazolyl, oxadiazolyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, purinyl, pteridinyl, naphthyridinyl, quinazolinyl, phthalazinyl, imidazopyridinyl, imidazothiazolyl, imidazooxazolyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, isoindolyl, indazolyl, pyrrolopyridyl, thienopyridyl, furopyridyl, benzothiadiazolyl, benzooxadiazolyl, pyrrolopyrimidyl, thienofuryl, and thienofuryl. In one embodiment, as preferred examples of "5-to 18-membered heteroaryl" there may be cited furyl, thienyl, pyrrolyl, imidazolyl, thiazolyl, pyrazolyl, oxazolyl, isoxazolyl, isothiazolyl, pyridyl, pyrimidinyl and carbazolyl, more preferably carbazolyl.
The term Cn-Cm cycloalkyl as used herein refers to a monocyclic or polycyclic alkyl group having n to m carbon atoms, e.g. C 3 -C 10 Cycloalkyl and C 3 -C 6 A cycloalkyl group. Examples include adamantyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and bicycloheptyl. In one embodiment, C 3 -C 10 The cycloalkyl group is preferably an adamantyl group or a cyclohexyl group.
The limited carbon number range of the group in the present invention means the number of carbon atoms of any integer included in the limited range, for example, C1 to C20 means that the number of carbon atoms of the group may be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20, C3 to C10 means that the number of carbon atoms of the group may be 3, 4, 5, 6, 7, 8, 9 or 10, and the limited carbon number ranges of other groups and so on.
The above preferred conditions may be combined arbitrarily to obtain preferred embodiments of the present invention without departing from the general knowledge in the art.
The reagents and starting materials used in the present invention are commercially available.
The preparation method of the pyrimidine derivative comprises the following steps:
1. the raw materials of various intermediates required by the pyrimidine derivatives are as follows:
2. synthetic examples
The method comprises the following steps of stirring a cyano-substituted aromatic compound (A1-A8) and a bromo-aromatic compound (B1-B2) in a trifluoroacetic anhydride solvent at normal temperature for 1-5 days to obtain a bromo intermediate product (II), and carrying out Suzuki coupling reaction on the bromo intermediate product (II) and a boric acid compound (C1-C30) to obtain a final product (I), wherein the specific synthetic route is as follows:
the specific preparation method of the compound is as follows:
in the first step, trifluoromethanesulfonic anhydride (1.1 eq) and a cyano-substituted aromatic compound (A1-A8) (2.2 eq) were dissolved in a dry dichloromethane solution (100 mL), and then the mixed solution was added to a dry one-neck flask, and a dichloromethane solution in which a bromoacetyl compound (B1-B2) (1.0 eq) was dissolved was dropwise added to the above mixed solution, and stirred at room temperature for 24 to 120 hours under a nitrogen protection condition. After the reaction is finished, removing a dichloromethane solvent under vacuum reduced pressure, and purifying by column chromatography to obtain an intermediate product (II);
and a second step of adding the intermediate (II) (1.0 eq), a boric acid compound (C1-C30) (1.2 eq) and potassium carbonate (1.8 eq) to a two-port bottle, adding a water/toluene mixed solvent (100 mL, water and toluene at a ratio of 1. The relevant characterization data of the target end product obtained are shown in table 1.
The product was characterized, wherein the elemental analysis used a test instrument, variao Micro Cube, agilent, usa, and the test element types were C, H, N, S. The instrument used for mass spectrometry is a U.S. Thermo Fisher TSQ Endura ultra-high performance liquid chromatography tandem triple quadrupole mass spectrometer.
TABLE 1 elemental analysis (C, H and N percent in compound), mass Spectrometry molecular weight and Synthesis reaction yield data for Compounds Pm-1 through Pm-15
3. Electroluminescent device embodiments
Some of the materials involved in the device embodiments have the following molecular structures:
the following embodiments of the organic electroluminescent device prepared by using the material disclosed by the invention have the following specific device preparation processes:
(1) Substrate treatment: the transparent ITO glass is used as a substrate material for preparing a device, then ultrasonic treatment is carried out for 30min by using 5 percent ITO washing liquor, then ultrasonic washing is carried out by using distilled water (2 times), acetone (2 times) and isopropanol (2 times) in sequence, and finally the ITO glass is stored in the isopropanol. Before each use, the surface of the ITO glass is carefully wiped by using acetone cotton balls and isopropanol cotton balls, and the ITO glass is dried after being washed by isopropanol and then is treated by plasma for 5min for later use.
(2) Hole injection lamination hole transport layer preparation: the hole transport layer is prepared by adopting an evaporation process, and when the vacuum degree of a vacuum evaporation system reaches 5 multiplied by 10 -4 Starting evaporation when the pressure is lower than Pa, sequentially depositing organic hole transport layers on the surface of the ITO electrode by a vacuum evaporation process at a deposition rate of a Cyens film thickness instrument, wherein the deposition rate of the hole transport material is
The layer was evaporated to α -NPD 30nm and CzSi 10nm.
(3) Preparing a luminescent layer: adopting vapor deposition process to prepare luminescent layer, when the vacuum degree of vacuum vapor deposition system reaches 5X 10 - 4 Starting evaporation when the pressure is lower than Pa, sequentially depositing a luminescent layer on the hole transport layer by a vacuum evaporation process at a deposition rate of a luminescent layer material from a Cyens film thickness meter
When the compound Pm-n (n = 1-158) is used as a luminescent material, the host material is DPEPO, and the doping concentration of the Pm-n (n = 1-158) is 5wt% -50 wt%. When the compound Pm-n (n = 1-158)) When the material is used as a main body material, the doping concentration is 50wt% -99 wt%. The layer thickness was 20nm.
(4) Preparing an electron transport layer, an electron injection layer and a metal electrode: the electron transmission layer, the electron injection layer and the metal electrode are prepared by adopting the evaporation process, and when the vacuum degree of a vacuum evaporation system reaches 5 multiplied by 10 -4 And starting evaporation when the pressure is lower than Pa, and sequentially depositing an organic electron transport layer, a LiF electron injection layer and a metal Al electrode on the luminescent layer by a vacuum evaporation process at a deposition rate according to a Schen film thickness instrument (the specific device structure is shown in figure 1). Wherein the organic material has a deposition rate of
Deposition rate of LiF
The deposition rate of Al is
The electron transport layer is TPBi, the thickness is 30nm, the thickness of LiF is 1nm, and the thickness of the metal electrode Al is 100nm.
The characteristics of the device such as current, voltage, brightness, light-emitting spectrum and the like are synchronously tested by a Photo Research PR 655 spectral scanning luminance meter and a Keithley K2400 digital source meter system. The performance test of the device is carried out at room temperature and in an ambient atmosphere. The External Quantum Efficiency (EQE) of the device was calculated from the current density, luminance and electroluminescence spectra in combination with the viewing function in the case of a lambertian emission, and the effects of the examples are shown in table 2.
TABLE 2 (D1-D80) Main parameters of organic electroluminescent Properties
Although the present invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some technical features may be equivalently replaced; and such modifications or substitutions do not depart from the spirit and scope of the corresponding technical solutions of the embodiments of the present invention.
Claims (8)
1. A pyrimidine derivative is characterized in that the pyrimidine derivative has a structure shown as the following formula (I):
wherein R is 1 、R 2 Each occurrence is independently C 6 ～C 14 Aryl radical, by one or more R a Substituted C 6 ～C 14 Aryl, 5-to 18-membered heteroaryl, substituted with one or more R a Substituted 5-to 18-membered heteroaryl;
R a independently at each occurrence, D (deuterium), fluorine, C 1 ～C 12 Alkyl radical, C 1 ～C 12 Alkoxy radical, C 3 ～C 10 Cycloalkyl, or C 6 ～C 14 An aryl group;
R 3 each occurrence is independently C 1 ～C 20 Alkyl radical, C 1 ～C 20 Alkoxy radical, C 3 -C 10 Cycloalkyl radical, C 6 ～C 14 Aryl radicals, substituted by one or more R b Substituted C 6 ～C 14 Aryl, 5-to 18-membered heteroaryl, substituted with one or more R b Substituted 5-to 18-membered heteroaryl, diphenylamino, or substituted with one or more R b A substituted diphenylamine group;
R b independently at each occurrence, D (deuterium), fluorine, C 1 ～C 12 Alkyl radical, C 1 ～C 12 Alkoxy radical, C 3 ～C 10 Cycloalkyl radical, C 6 ～C 14 Aryl radical, by one or more R c Substituted C 6 ～C 14 Aryl, 5-to 18-membered heteroaryl, substituted with one or more R c Substituted 5-to 18-membered heteroaryl, diphenylamino, or substituted with one or more R c A substituted diphenylamine group;
R c independently at each occurrence, D (deuterium), fluorine, C 1 ～C 12 Alkyl radical, C 1 ～C 12 Alkoxy radical, C 3 ～C 10 Cycloalkyl, C 6 ～C 14 Aryl, C substituted by one or more Rc 6 ～C 14 Aryl radicals, substituted by one or more R d Substituted C 6 ～C 14 Aryl, 5-to 18-membered heteroaryl, substituted with one or more R d Substituted 5-to 18-membered heteroaryl, diphenylamino, or substituted with one or more R d A substituted diphenylamine group;
R d independently at each occurrence, D (deuterium), fluorine, C 1 ～C 12 Alkyl radical, C 1 ～C 12 Alkoxy radical, C 3 ～C 10 Cycloalkyl, or C 6 ～C 14 An aryl group;
the above alkyl, alkoxy, cycloalkyl, aryl, heteroaryl groups are optionally substituted with one or more substituents selected from the group consisting of: halogen, -CN, C1-C12 alkyl, C1-C12 alkoxy, C1-C12 haloalkyl, C2-C6 alkenyl, C3-C10 cycloalkyl, C6-C14 aryl, and 5-to 18-membered heteroaryl.
2. A pyrimidine derivative according to claim 1, wherein the pyrimidine derivative is selected from any one of the formulae (Pm-1) to (Pm-158):
3. an organic electroluminescent material, characterized in that the organic electroluminescent material comprises the pyrimidine derivative according to any one of claims 1 to 2.
4. An organic electroluminescent device comprising an anode, a cathode, and an organic thin film layer interposed between the anode and the cathode, the organic thin film layer comprising a light-emitting layer, an optional hole-injecting layer, an optional hole-transporting layer, an optional electron-transporting layer, and an optional electron-injecting layer; wherein at least one of the light-emitting layer, the electron-injecting layer, the electron-transporting layer, the hole-transporting layer, and the hole-injecting layer comprises the pyrimidine derivative according to any one of claims 1 to 2.
5. The organic electroluminescent device according to claim 4, further comprising an optional hole blocking layer, an optional electron blocking layer, and an optional capping layer.
6. The organic electroluminescent device according to claim 4, further comprising a substrate, an anode layer, an organic light emitting functional layer and a cathode layer sequentially formed on the substrate; the organic light-emitting functional layer comprises a light-emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer, wherein the light-emitting layer comprises the pyrimidine derivative as claimed in any one of claims 1-2.
7. Use of an organic electroluminescent device as claimed in claim 4, characterized in that the organic electroluminescent device is used for the production of organic electroluminescent displays or illumination sources.
8. A process for preparing a pyrimidine derivative according to claim 1, which comprises the step of:
dissolving trifluoromethanesulfonic anhydride and a cyano raw material compound (A) in a dry dichloromethane solution, adding the mixed solution into a dry single-mouth bottle, dropwise adding a dichloromethane solution dissolved with a bromoacetyl compound (B) into the mixed solution, stirring at room temperature for 24-120 hours under the protection of nitrogen, removing the dichloromethane solvent under vacuum reduced pressure after the reaction is finished, and purifying by using column chromatography to obtain an intermediate product (II);
and secondly, adding the intermediate product (II), the boric acid compound (C) and potassium carbonate into a double-mouth bottle, then adding a mixed solvent of water and toluene, adding tetrakis (triphenylphosphine) palladium under the condition of nitrogen, ventilating, carrying out reflux reaction for 6-24 hours, and after the reaction is finished, extracting, carrying out column chromatography and sublimating to obtain the final product (I).
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