CN108976166A - A kind of compound and its preparation method and application - Google Patents
A kind of compound and its preparation method and application Download PDFInfo
- Publication number
- CN108976166A CN108976166A CN201810598646.2A CN201810598646A CN108976166A CN 108976166 A CN108976166 A CN 108976166A CN 201810598646 A CN201810598646 A CN 201810598646A CN 108976166 A CN108976166 A CN 108976166A
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- Prior art keywords
- phenyl
- formula
- propyl
- butyl
- tert
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 56
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 238000005401 electroluminescence Methods 0.000 claims abstract description 12
- -1 3- tert-butyl-phenyl Chemical group 0.000 claims description 117
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 37
- 150000002431 hydrogen Chemical class 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 33
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 16
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000005561 phenanthryl group Chemical group 0.000 claims description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 claims 1
- 239000010410 layer Substances 0.000 description 76
- 239000002585 base Substances 0.000 description 26
- 229910052709 silver Inorganic materials 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 4
- XPDWGBQVDMORPB-UHFFFAOYSA-N trifluoromethane acid Natural products FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 4
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 230000005611 electricity Effects 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 230000027756 respiratory electron transport chain Effects 0.000 description 3
- 229910001316 Ag alloy Inorganic materials 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001339 alkali metal compounds Chemical class 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
- HONWGFNQCPRRFM-UHFFFAOYSA-N 2-n-(3-methylphenyl)-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical class CC1=CC=CC(N(C=2C=CC=CC=2)C=2C(=CC=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HONWGFNQCPRRFM-UHFFFAOYSA-N 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- ONCLISNXFKIUGP-UHFFFAOYSA-N C(CC=CC1C23C4=CCCC=C4c(cc4)c2cc4N(C2=CC=CCC2)c2ccccn2)C1c1c3cccc1 Chemical compound C(CC=CC1C23C4=CCCC=C4c(cc4)c2cc4N(C2=CC=CCC2)c2ccccn2)C1c1c3cccc1 ONCLISNXFKIUGP-UHFFFAOYSA-N 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- 229910000861 Mg alloy Inorganic materials 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 229910045601 alloy Inorganic materials 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
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical group [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- DKQSRQLSDPYGCJ-UHFFFAOYSA-N n-phenylpyridin-4-amine Chemical compound C=1C=NC=CC=1NC1=CC=CC=C1 DKQSRQLSDPYGCJ-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000005036 potential barrier Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/20—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/22—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to two ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/85—Arrangements for extracting light from the devices
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present invention provides a kind of compounds and its preparation method and application, the experimental results showed that, compound provided by the invention can significantly improve luminous efficiency and the service life of organic electroluminescence device as the CPL layer in organic electroluminescence device.
Description
Technical field
The present invention relates to organic photoelectrical material technical fields, more particularly, to a kind of compound and preparation method thereof and answer
With.
Background technique
The correlative study of organic electroluminescence device is initiated at the sixties in 19th century, until the end of the eighties OLED just vigorously send out
Exhibition is got up.There is OLED all solid state, low-voltage driving, active to shine, response quickly, wide viewing angle, light-emitting area are big, emission wavelength covers
Cover entire visible region and it is rich in color the advantages that, realizing that panchromatic large-area displays field has very big advantage, becoming
The flat-panel display device of great prospect.The light emission luminance of organic electroluminescence device is proportional to the concentration and exciton of hole and electronics
The probability of recombination product, it is desirable to obtain higher luminous efficiency, not only need hole and electronics that can be efficiently injected into, transmit and
It is compound and hole and electron injection is required to reach balance.Therefore, in organic electroluminescence device, between organic layer and organic layer
It is matched with the energy band of two electrodes extremely important to device recombination luminescence.
In order to optimize the properties with balancing device, people introduce the functional layer of a variety of different roles, such as hole
Implanted layer, hole blocking layer etc..The effect that hole injection layer is added between ito anode and hole transmission layer is mainly manifested in drop
Low interface potential barrier, the Adhering capacity for increasing hole transmission layer and ITO electrode improve its stability and balance electronic and hole note
Enter etc..
Further, since greatly being constrained between the external quantum efficiency and internal quantum efficiency of OLED there are huge gap
The development of OLED, therefore, the light extraction efficiency for how improving OLED also have become a hot topic of research.Ito thin film and glass substrate
The interface of interface and glass substrate and air can be totally reflected, and be accounted for about before being emitted to OLED device to the light of exterior space
The 20% of organic material film EL total amount, it is thin that remaining about 80% light is mainly limited in organic material film, ITO in the form of guided wave
In film and glass substrate, the development and application of OLED are seriously constrained, the total reflection effect in OLED device how is reduced, improves
The performance drawn optically coupling to before device to the ratio of exterior space, and then improve device has played the extensive concern of people.
Summary of the invention
In view of this, technical problem to be solved by the present invention lies in provide a kind of compound and preparation method thereof and answer
With CPL layer of the compound provided by the invention as OLED device can be improved the efficiency of luminescent device.
The present invention provides a kind of compounds, have structure shown in formula (I),
Wherein, the Ar1、Ar2The independent heteroaryl selected from hydrogen, the alkyl of C1~C8, the aryl of C6~C25 or C2~C20
Base；
The X1-a、X1-b、X1-c、X1-d、X1-eIt is independent to be selected from nitrogen or carbon, and the X1-a、X1-b、X1-c、X1-d、X1-eIn extremely
Rare 1 is nitrogen；
The A is formula (A-1), formula (A-2) or formula (A-3),
The R1、R2、R3、R4、R5、R6The independent aryl selected from hydrogen, the alkyl of C1~C3 or C6~C10,
Or the R1And R2The condensed ring radical of C10~C20 is formed with the carbon where it.
Preferably, the Ar1Selected from hydrogen, the alkyl of C1~C5, phenyl, the alkyl-substituted phenyl of C1~C5, C10~C20
Fused ring aryl, the sulfur-bearing heteroaryl of C3~C15 or the nitrogenous heteroaryl of C3~C15；
The Ar2Selected from hydrogen, the alkyl of C1~C5, phenyl, the alkyl-substituted phenyl of C1~C5, C10~20 condensed ring
The nitrogenous heteroaryl of aryl, the sulfur-bearing heteroaryl of C3~C15 or C3~C15.
Preferably, the Ar1Selected from hydrogen, methyl, ethyl, propyl, normal-butyl, tert-butyl, amyl, trifluoromethyl, phenyl,
Anthryl, naphthalene, phenanthryl, 3- tert-butyl-phenyl, 3- trifluoromethyl, 3- n-propyl phenyl, 3- isopropyl phenyl, 3- methylbenzene
Base, 4- tert-butyl-phenyl, 4- trifluoromethyl, 4- n-propyl phenyl, 4- isopropyl phenyl, 4- aminomethyl phenyl, 3,5- diformazan
Base phenyl, 2- thienyl, pyridyl group, pyridazinyl, pyrazinyl, triazine radical or acridinyl；
The Ar2Selected from hydrogen, methyl, ethyl, propyl, normal-butyl, tert-butyl, amyl, trifluoromethyl, phenyl, anthryl, naphthalene
Base, phenanthryl, 3- tert-butyl-phenyl, 3- trifluoromethyl, 3- n-propyl phenyl, 3- isopropyl phenyl, 3- aminomethyl phenyl, uncle 4-
Butyl phenyl, 4- trifluoromethyl, 4- n-propyl phenyl, 4- isopropyl phenyl, 4- aminomethyl phenyl, 3,5- 3,5-dimethylphenyl,
2- thienyl, pyridyl group, pyridazinyl, pyrazinyl, triazine radical or acridinyl.
Preferably, the X1-a、X1-b、X1-c、X1-d、X1-eIn at most have 3 for nitrogen.
Preferably, the R1、R2It is independent to be selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, phenyl, anthryl, naphthalene, phenanthrene
Base, 3- tert-butyl-phenyl, 3- trifluoromethyl, 3- n-propyl phenyl, 3- isopropyl phenyl, 3- aminomethyl phenyl, 4- tert-butyl
Phenyl, 4- trifluoromethyl, 4- n-propyl phenyl, 4- isopropyl phenyl or 4- aminomethyl phenyl；
Or the R1And R2Fluorenyl is formed with the carbon where it.
Preferably, the R3、R4、R5、R6It is independent selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, phenyl, anthryl,
Naphthalene, phenanthryl, 3- tert-butyl-phenyl, 3- trifluoromethyl, 3- n-propyl phenyl, 3- isopropyl phenyl, 3- aminomethyl phenyl, 4-
Tert-butyl-phenyl, 4- trifluoromethyl, 4- n-propyl phenyl, 4- isopropyl phenyl or 4- aminomethyl phenyl.
Preferably, formula (I) compound represented is formula (I-1), formula (I-2), formula (I-3), formula (I-4), formula (I-5)
Or formula (I-6),
Wherein, the Ar1、Ar2The independent heteroaryl selected from hydrogen, the alkyl of C1~C8, the aryl of C6~C25 or C2~C20
Base；
The X1-a、X1-b、X1-c、X1-d、X1-eIt is independent to be selected from nitrogen or carbon, and the X1-a、X1-b、X1-c、X1-d、X1-eIn extremely
Rare 1 is nitrogen.
Preferably, formula (I) compound represented is formula (001)~formula (162).
The present invention also provides a kind of preparation methods of formula (I) compound, comprising: by the chemical combination of A-Br and formula (II) structure
Object reaction, obtains the compound of formula (I) structure；
Wherein, the Ar1、Ar2The independent heteroaryl selected from hydrogen, the alkyl of C1~C8, the aryl of C6~C25 or C2~C20
Base；
The X1-a、X1-b、X1-c、X1-d、X1-eIt is independent to be selected from nitrogen or carbon, and the X1-a、X1-b、X1-c、X1-d、X1-eIn extremely
Rare 1 is nitrogen:
The A is formula (A-1), formula (A-2) or formula (A-3),
The R1、R2、R3、R4、R5、R6The independent aryl selected from hydrogen, the alkyl of C1~C3 or C6~C10,
Or the R1And R2The condensed ring radical of C10~C20 is formed with the carbon where it.
The present invention also provides a kind of formula (I) compounds represented of the present invention as CPL layers is preparing Organic Electricity
Application in electroluminescence device.
Compared with prior art, the present invention provides a kind of compounds and its preparation method and application, the experimental results showed that,
Compound provided by the invention can significantly improve organic electroluminescence as the CPL layer in organic electroluminescence device
The luminous efficiency of part and service life.
Specific embodiment
A kind of compound has structure shown in formula (I),
Wherein, the Ar1、Ar2The independent heteroaryl selected from hydrogen, the alkyl of C1~C8, the aryl of C6~C25 or C2~C20
Base；
The X1-a、X1-b、X1-c、X1-d、X1-eIt is independent to be selected from nitrogen or carbon, and the X1-a、X1-b、X1-c、X1-d、X1-eIn extremely
Rare 1 is nitrogen；
The A is formula (A-1), formula (A-2) or formula (A-3),
The R1、R2、R3、R4、R5、R6The independent aryl selected from hydrogen, the alkyl of C1~C3 or C6~C10,
Or the R1And R2The condensed ring radical of C10~C20 is formed with the carbon where it.
According to the present invention, the Ar1Preferably hydrogen, the alkyl of C1~C5, phenyl, the alkyl-substituted phenyl of C1~C5, C10
The nitrogenous heteroaryl of~20 fused ring aryl, the sulfur-bearing heteroaryl of C3~C15 or C3~C15；More preferably hydrogen, methyl, ethyl,
Propyl, normal-butyl, tert-butyl, amyl, trifluoromethyl, phenyl, anthryl, naphthalene, phenanthryl, 3- tert-butyl-phenyl, 3- trifluoromethyl
Phenyl, 3- n-propyl phenyl, 3- isopropyl phenyl, 3- aminomethyl phenyl, 4- tert-butyl-phenyl, 4- trifluoromethyl, 4- positive third
Base phenyl, 4- isopropyl phenyl, 4- aminomethyl phenyl, 3,5- 3,5-dimethylphenyl, 2- thienyl, pyridyl group, pyridazinyl, pyrazinyl,
Triazine radical or acridinyl；The Ar2Preferably hydrogen, the alkyl of C1~C5, phenyl, the alkyl-substituted phenyl of C1~C5, C10~20
Fused ring aryl, the sulfur-bearing heteroaryl of C3~C15 or the nitrogenous heteroaryl of C3~C15；More preferably hydrogen, methyl, ethyl, third
Base, normal-butyl, tert-butyl, amyl, trifluoromethyl, phenyl, anthryl, naphthalene, phenanthryl, 3- tert-butyl-phenyl, 3- trifluoromethylbenzene
Base, 3- n-propyl phenyl, 3- isopropyl phenyl, 3- aminomethyl phenyl, 4- tert-butyl-phenyl, 4- trifluoromethyl, 4- n-propyl
Phenyl, 4- isopropyl phenyl, 4- aminomethyl phenyl, 3,5- 3,5-dimethylphenyl, 2- thienyl, pyridyl group, pyridazinyl, pyrazinyl, three
Piperazine base or acridinyl.
According to the present invention, X1-a、X1-b、X1-c、X1-d、X1-eIn preferably have one be nitrogen, two be nitrogen or three are nitrogen.
According to the present invention, the R1 is preferably hydrogen, methyl, ethyl, n-propyl, isopropyl, phenyl, anthryl, naphthalene, phenanthrene
Base, 3- tert-butyl-phenyl, 3- trifluoromethyl, 3- n-propyl phenyl, 3- isopropyl phenyl, 3- aminomethyl phenyl, 4- tert-butyl
Phenyl, 4- trifluoromethyl, 4- n-propyl phenyl, 4- isopropyl phenyl or 4- aminomethyl phenyl；The R2Preferably hydrogen, first
Base, ethyl, n-propyl, isopropyl, phenyl, anthryl, naphthalene, phenanthryl, 3- tert-butyl-phenyl, 3- trifluoromethyl, 3- positive third
Base phenyl, 3- isopropyl phenyl, 3- aminomethyl phenyl, 4- tert-butyl-phenyl, 4- trifluoromethyl, 4- n-propyl phenyl, 4- are different
Propyl phenyl or 4- aminomethyl phenyl；Or R described in person1Fluorenyl is formed with the carbon where R2 and its.
The R3Preferably hydrogen, methyl, ethyl, n-propyl, isopropyl, phenyl, anthryl, naphthalene, phenanthryl, 3- tert-butyl benzene
Base, 3- trifluoromethyl, 3- n-propyl phenyl, 3- isopropyl phenyl, 3- aminomethyl phenyl, 4- tert-butyl-phenyl, 4- fluoroform
Base phenyl, 4- n-propyl phenyl, 4- isopropyl phenyl or 4- aminomethyl phenyl.
The R4Preferably hydrogen, methyl, ethyl, n-propyl, isopropyl, phenyl, anthryl, naphthalene, phenanthryl, 3- tert-butyl benzene
Base, 3- trifluoromethyl, 3- n-propyl phenyl, 3- isopropyl phenyl, 3- aminomethyl phenyl, 4- tert-butyl-phenyl, 4- fluoroform
Base phenyl, 4- n-propyl phenyl, 4- isopropyl phenyl or 4- aminomethyl phenyl.
The R5Preferably hydrogen, methyl, ethyl, n-propyl, isopropyl, phenyl, anthryl, naphthalene, phenanthryl, 3- tert-butyl benzene
Base, 3- trifluoromethyl, 3- n-propyl phenyl, 3- isopropyl phenyl, 3- aminomethyl phenyl, 4- tert-butyl-phenyl, 4- fluoroform
Base phenyl, 4- n-propyl phenyl, 4- isopropyl phenyl or 4- aminomethyl phenyl.
The R6Preferably hydrogen, methyl, ethyl, n-propyl, isopropyl, phenyl, anthryl, naphthalene, phenanthryl, 3- tert-butyl benzene
Base, 3- trifluoromethyl, 3- n-propyl phenyl, 3- isopropyl phenyl, 3- aminomethyl phenyl, 4- tert-butyl-phenyl, 4- fluoroform
Base phenyl, 4- n-propyl phenyl, 4- isopropyl phenyl or 4- aminomethyl phenyl.
Specifically, formula (I) compound represented is formula (I-1), formula (I-2), formula (I-3), formula (I-4), formula (I-
5) or formula (I-6),
Wherein, the Ar1、Ar2The independent heteroaryl selected from hydrogen, the alkyl of C1~C8, the aryl of C6~C25 or C2~C20
Base；
The X1-a、X1-b、X1-c、X1-d、X1-eIt is independent to be selected from nitrogen or carbon, and the X1-a、X1-b、X1-c、X1-d、X1-eIn extremely
Rare 1 is nitrogen.
More specifically, formula (I) compound represented is formula (001)~formula (161),
The present invention also provides a kind of preparation methods of formula (I) compound, comprising: by the chemical combination of A-Br and formula (II) structure
Object reaction, obtains the compound of formula (I) structure；
Wherein, the Ar1、Ar2The independent heteroaryl selected from hydrogen, the alkyl of C1~C8, the aryl of C6~C25 or C2~C20
Base；
The X1-a、X1-b、X1-c、X1-d、X1-eIt is independent to be selected from nitrogen or carbon, and the X1-a、X1-b、X1-c、X1-d、X1-eIn extremely
Rare 1 is nitrogen；
The A is formula (A-1), formula (A-2) or formula (A-3),
The R1、R2、R3、R4、R5、R6The independent aryl selected from hydrogen, the alkyl of C1~C3 or C6~C10,
Or the R1And R2The condensed ring radical of C10~C20 is formed with the carbon where it.
Wherein, the present invention does not have particular/special requirement to the condition of reaction, and those skilled in the art can select according to common knowledge
It selects suitable reaction condition and product is prepared, and the restriction of group is identical as aforesaid compound.
The present invention also provides a kind of formula (I) compounds represented of the present invention as CPL layers is preparing Organic Electricity
Application in electroluminescence device.
The present invention provides a kind of compound and its preparation method and application, compound provided by the invention is as Organic Electricity
CPL layer in electroluminescence device, can significantly improve luminous efficiency and the service life of organic electroluminescence device.And preparation side
Method is simple, and raw material sources are extensive, is suitable for industrialized production.
In addition, in the present inventionRepresent the connecting key of group；In-N represent the key can be in any one of aryl
Position.
It is clearly and completely described below in conjunction with the technical solution of the embodiment of the present invention, it is clear that described implementation
Example is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, this field is common
Technical staff's every other embodiment obtained without making creative work belongs to the model that the present invention protects
It encloses.
Embodiment 1
The synthesis of compound 001
Under condition of nitrogen gas, N- phenylpyridine -4- amine (110mmol), bromo- 9, the 9- dimethyl -9H- fluorenes (100mmol) of 2-, neighbour
Phenanthroline (1.98g), cuprous iodide (1.90g), the substances such as cesium carbonate (38.6g, 2eq) are dissolved in heating in toluene (300mL)
It 110 DEG C, reacts 7 hours, cooling, room temperature filtering removes metallics, evaporates solvent with revolving, obtain solid 001
(76mmolg, 76%).
With identical mole ratio It replaces in the synthesis of compound 001
'sWith chemical formulaReaction, is prepared shown in general formula 1
Compound.
Embodiment 2
Organic compound of the invention has high Tg (glass transition temperature) as the CPL layer material in luminescent device,
High refractive index, the test of hot property and refractive index is carried out to the compound of embodiment preparation respectively, and testing result is as shown in table 1.
Table 1
Embodiment 3
It is applied to the preparation of OLED device using formula of the present invention (I) compound as CPL layers, in the present embodiment
OLED device is top radiation organic EL part, and structure includes: substrate 1, and on substrate 1 successively plating formed it is anti-
Penetrate layer 2, anode 3, hole injection layer (HIL) 4, hole transmission layer (HTL) 5, luminescent layer (EML) 6, electron transfer layer (ETL) 7,
Electron injecting layer (EIL) 8, cathode 9 and coating 10.
Wherein, substrate 1 is glass substrate, quartz base plate or flexible macromolecule substrate (plastics or polyimides etc.)；
Reflecting layer 2 can be metallic silver or silver alloy, metal aluminum or aluminum alloy layer, for reflecting the light of incident orientation substrate
Line；
Anode layer 3 can be ITO (tin indium oxide), IZO (indium zinc oxide), high-work-function metal or alloy, C60 etc. organic half
Conductor material；
Hole injection layer 4 selects 4,4 ', 4 "-three (N-3- methylphenyl-N-phenyl amino) triphenylamines (MTDATA) and 2,
The mixture of 3,5,6- tetrafluoro Kui bismethanes (F4TCNQ), the mass ratio of the two are 25: 1.
Hole transmission layer 5 is N, N '-two-(1- naphthalene)-N, diphenyl -1 N ' -, 1 '-xenyl -4,4 '-diamines (NPB).
Luminescent layer 6 can be feux rouges, green light or blue light.Wherein, the main body RH of feux rouges is Bebq2 (bis- (10- hydroxy benzos
[h] quinoline) beryllium), doping RD be Ir (piq) 2 (acac), the main body GH of green light is CBP (4,4 '-bis- (N- carbazoles) -1,1 '-connection
Benzene), doping GD be Ir (ppy) 3, blue light main body BH be ADN, doping BD be DPAVB (Isosorbide-5-Nitrae-two-[4- (diformazan aminophenyl) benzene second
Alkenyl] benzene).
Electron transfer layer 7 is Bphen.Electron injecting layer 8 can be inorganic alkali metal compounds or organic alkali metal complex.
Preferred as alkali is that inorganic alkali metal compounds are LiF, and organic alkali metal complex is 8-hydroxy-quinoline lithium.
The method for specifically preparing device is as follows:
Blue-light device
Substrate 1 is glass substrate, and sputtering sedimentation Ag sputters 10nm's as reflecting layer 2 with a thickness of 150nm on substrate 1
Anode 3 of the ITO as device, and required figure is etched, use O3Plasma treatment 3 minutes.Gained substrate 1 is placed in vacuum
In, by the mixture of the total MTDATA and F4TCNQ for steaming deposition 130nm as hole injection layer (HIL) 4, wherein F4TCNQ weight
Amount is the 4% of MTDATA weight.Then the NPB of 10nm is deposited as hole transmission layer (HTL) 5.Steam the ADN of deposition 30nm altogether again
Mixture with DPAVB is as luminescent layer 6, and wherein the molar ratio of DPAVB and ADN is 1: 20.Then the Bphen for depositing 20nm makees
For electron transfer layer (ETL) 7.The LiF of 1nm is deposited again as electron injecting layer 8.Cathode 9 is the alloy-layer of co-evaporation K and Ag
10nm, wherein K passes through KBH4The mode that (400 DEG C of temperature) is decomposed during vapor deposition is deposited, K and Ag molar ratio is 8: 1, then
Deposit the Ag of 25nm.The compounds of this invention 001 that 30nm is deposited is used as CPL layers.
Green device
It is consistent with the preparation method of blue-light device, the thickness of HIL is only changed to 170nm, the material of luminescent layer is changed to CBP
With the mixture of Ir (ppy) 3, the wherein molar ratio 1: 10 of Ir (ppy) 3 and CBP.
Red device
It is consistent with the preparation method of blue-light device, the thickness of HIL is only changed to 60nm, the material of luminescent layer is changed to
BeBq2With Ir (piq)2(acac) mixture, wherein Ir (piq)2(acac) and BeBq2Molar ratio be 1: 10.
Embodiment 4
Specific implementation step is unique the difference is that cathode 9 with embodiment 3 are as follows: K and Ag alloy-layer, molar ratio 2: 1 are thick
Degree is 7nm；Ag layers are 25nm；CPL layers prepare red device for the compounds of this invention 037 with a thickness of 50nm.
Embodiment 5
Specific implementation step is unique the difference is that cathode 9 with embodiment 3 are as follows: Mg and Ag alloy-layer, molar ratio 4: 1 are thick
Degree is 5nm；Ag layers are 20nm；CPL layers are the compounds of this invention 061, with a thickness of 60nm, prepare green device.
Embodiment 6
Specific implementation step is unique the difference is that cathode 9 with embodiment 3 are as follows: Mg and Ag alloy-layer, molar ratio 6: 1 are thick
Degree is 7nm；Ag layers are 25nm；CPL layers prepare red device for the compounds of this invention 085 with a thickness of 30nm.
Embodiment 7
Specific implementation step is unique the difference is that cathode 9 with embodiment 3 are as follows: Li and Ag alloy-layer, molar ratio 8: 1 are thick
Degree is 9nm；Ag layers are 30nm；CPL layers are the compounds of this invention 109, with a thickness of 50nm, prepare green device.
Embodiment 8
Specific implementation step is unique the difference is that cathode 9 with embodiment 3 are as follows: Mg and Ag alloy-layer, molar ratio 4: 1 are thick
Degree is 11nm；Ag layers are 20nm；CPL layers prepare blue-light device for the compounds of this invention 139 with a thickness of 45nm.
Embodiment 9
Specific implementation step is unique the difference is that cathode 9 with embodiment 3 are as follows: Mg and Ag alloy-layer, molar ratio 4: 1 are thick
Degree is 11nm；Ag layers are 20nm；CPL layers prepare blue-light device for the compounds of this invention 013 with a thickness of 45nm.
Embodiment 10
Specific implementation step is unique the difference is that cathode 9 with embodiment 3 are as follows: Mg and Ag alloy-layer, molar ratio 4: 1 are thick
Degree is 3nm；Ag layers are 15nm；CPL layers prepare blue-light device for the compounds of this invention 049 with a thickness of 100nm.
11~embodiment of embodiment 15
Specific implementation step is unique the difference is that cathode 9 with embodiment 3 are as follows: Mg and Ag alloy-layer, molar ratio 6: 1 are thick
Degree is 7nm；Ag layers are 25nm；CPL layers are the compounds of this invention 002,015,028,041,054, with a thickness of 30nm, prepare feux rouges
Device.
16~embodiment of embodiment 19
Specific implementation step is unique the difference is that cathode 9 with embodiment 3 are as follows: Li and Ag alloy-layer, molar ratio 8: 1 are thick
Degree is 9nm；Ag layers are 30nm；CPL layers prepare green light device for the compounds of this invention 067,080,093,106 with a thickness of 50nm
Part.
20~embodiment of embodiment 23
Specific implementation step is unique the difference is that cathode 9 with embodiment 3 are as follows: Mg and Ag alloy-layer, molar ratio 4: 1 are thick
Degree is 3nm；Ag layers are 15nm；CPL layers prepare blue light device for the compounds of this invention 119,132,145,158 with a thickness of 100nm
Part.
Comparative example 1
This comparative example is OLED device preparation embodiment, and specific steps are as described in Example 3, unique the difference is that described
The transparent composite cathode 9 of OLED only includes the alloy-layer of the low workfunction metal and Ag that set gradually, Ag layers, does not include CPL layers, system
Standby red device, green device and blue-light device.
Comparative example 2
OLED device preparation step is with embodiment 3 in this comparative example, the difference is that the cathode 9 is a kind of compound yin of OLED
Pole structure, the OLED composite cathode structure include the alloy-layer of the low workfunction metal and Ag set gradually, Ag layers.Specific step
It is rapid as follows: under vacuum conditions, using hot evaporation technology, Mg/Ag alloy material to be deposited as the alloy-layer, Mg/Ag's rubs
You than be 1: 1, the alloy-layer with a thickness of 10nm；Under vacuum conditions, using hot evaporation technology, in the alloy-layer
Top be deposited one layer Ag layers, with a thickness of 10nm, prepare red device, green device and blue-light device.
Embodiment 24
The performance for the OLED device that embodiment 3~23 and comparative example 1~2 obtain is tested, the results are shown in Table 2.
Table 2
As can be seen from the above table, the device of same type, the device in embodiment are imitated than the electric current of the device in comparative example
Rate, brightness service life are more preferable.
The above description of the embodiment is only used to help understand the method for the present invention and its core ideas.It should be pointed out that pair
For those skilled in the art, without departing from the principle of the present invention, the present invention can also be carried out
Some improvements and modifications, these improvements and modifications also fall within the scope of protection of the claims of the present invention.
Claims (10)
1. a kind of compound has structure shown in formula (I),
Wherein, the Ar1、Ar2The independent heteroaryl selected from hydrogen, the alkyl of C1~C8, the aryl of C6~C25 or C2~C20；
The X1-a、X1-b、X1-c、X1-d、X1-eIt is independent to be selected from nitrogen or carbon, and the X1-a、X1-b、X1-c、X1-d、X1-eIn at least
1 is nitrogen；
The A is formula (A-1), formula (A-2) or formula (A-3),
The R1、R2、R3、R4、R5、R6The independent aryl selected from hydrogen, the alkyl of C1~C3 or C6~C10,
Or the R1And R2The condensed ring radical of C10~C20 is formed with the carbon where it.
2. compound according to claim 1, which is characterized in that the Ar1Selected from hydrogen, the alkyl of C1~C5, phenyl, C1
The alkyl-substituted phenyl of~C5, the fused ring aryl of C10~C20, the nitrogenous heteroaryl of the sulfur-bearing heteroaryl of C3~C15 or C3~C15
Base；
The Ar2Selected from hydrogen, the alkyl of C1~C5, phenyl, the alkyl-substituted phenyl of C1~C5, C10~20 fused ring aryl,
The sulfur-bearing heteroaryl of C3~C15 or the nitrogenous heteroaryl of C3~C15.
3. compound according to claim 1, which is characterized in that the Ar1Selected from hydrogen, methyl, ethyl, propyl, positive fourth
Base, tert-butyl, amyl, trifluoromethyl, phenyl, anthryl, naphthalene, phenanthryl, 3- tert-butyl-phenyl, 3- trifluoromethyl, 3- are just
Propyl phenyl, 3- isopropyl phenyl, 3- aminomethyl phenyl, 4- tert-butyl-phenyl, 4- trifluoromethyl, 4- n-propyl phenyl, 4-
Isopropyl phenyl, 4- aminomethyl phenyl, 3,5- 3,5-dimethylphenyl, 2- thienyl, pyridyl group, pyridazinyl, pyrazinyl, triazine radical or a word used for translation
Piperidinyl；
The Ar2Selected from hydrogen, methyl, ethyl, propyl, normal-butyl, tert-butyl, amyl, trifluoromethyl, phenyl, anthryl, naphthalene, phenanthrene
Base, 3- tert-butyl-phenyl, 3- trifluoromethyl, 3- n-propyl phenyl, 3- isopropyl phenyl, 3- aminomethyl phenyl, 4- tert-butyl
Phenyl, 4- trifluoromethyl, 4- n-propyl phenyl, 4- isopropyl phenyl, 4- aminomethyl phenyl, 3,5- 3,5-dimethylphenyl, 2- thiophene
Pheno base, pyridyl group, pyridazinyl, pyrazinyl, triazine radical or acridinyl.
4. compound according to claim 1, which is characterized in that the X1-a、X1-b、X1-c、X1-d、X1-eIn at most have 3
For nitrogen.
5. compound according to claim 1, which is characterized in that the R1、R2It is independent selected from hydrogen, methyl, ethyl, just
Propyl, isopropyl, phenyl, anthryl, naphthalene, phenanthryl, 3- tert-butyl-phenyl, 3- trifluoromethyl, 3- n-propyl phenyl, 3- are different
Propyl phenyl, 3- aminomethyl phenyl, 4- tert-butyl-phenyl, 4- trifluoromethyl, 4- n-propyl phenyl, 4- isopropyl phenyl or 4-
Aminomethyl phenyl；
Or the R1And R2Fluorenyl is formed with the carbon where it.
6. compound according to claim 1, which is characterized in that the R3、R4、R5、R6It is independent to be selected from hydrogen, methyl, second
Base, n-propyl, isopropyl, phenyl, anthryl, naphthalene, phenanthryl, 3- tert-butyl-phenyl, 3- trifluoromethyl, 3- n-propylbenzene
Base, 3- isopropyl phenyl, 3- aminomethyl phenyl, 4- tert-butyl-phenyl, 4- trifluoromethyl, 4- n-propyl phenyl, 4- isopropyl
Phenyl or 4- aminomethyl phenyl.
7. compound according to claim 1, which is characterized in that formula (I) compound represented is formula (I-1), formula
(I-2), formula (I-3), formula (I-4), formula (I-5) or formula (I-6)
Wherein, the Ar1、Ar2The independent heteroaryl selected from hydrogen, the alkyl of C1~C8, the aryl of C6~C25 or C2~C20；
The X1-a、X1-b、X1-c、X1-d、X1-eIt is independent to be selected from nitrogen or carbon, and the X1-a、X1-b、X1-c、X1-d、X1-eIn at least
1 is nitrogen.
8. compound according to claim 1, which is characterized in that formula (I) compound represented is formula (001)~formula
(162),
9. a kind of preparation method of formula (I) compound, comprising: react A-Br with the compound of formula (II) structure, obtain formula (I)
The compound of structure；
Wherein, the Ar1、Ar2The independent heteroaryl selected from hydrogen, the alkyl of C1~C8, the aryl of C6~C25 or C2~C20；
The X1-a、X1-b、X1-c、X1-d、X1-eIt is independent to be selected from nitrogen or carbon, and the X1-a、X1-b、X1-c、X1-d、X1-eIn at least
1 is nitrogen；
The A is formula (A-1), formula (A-2) or formula (A-3),
The R1、R2、R3、R4、R5、R6The independent aryl selected from hydrogen, the alkyl of C1~C3 or C6~C10,
Or the R1And R2The condensed ring radical of C10~C20 is formed with the carbon where it.
10. formula (I) compound represented described in a kind of 1~claim 8 of claim any one is being prepared as CPL layers
Application in organic electroluminescence device.
Priority Applications (1)
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109824522A (en) * | 2019-03-29 | 2019-05-31 | 吉林奥来德光电材料股份有限公司 | A kind of organic luminescent compounds and its preparation method and application |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07281464A (en) * | 1994-04-08 | 1995-10-27 | Canon Inc | Electrophotographic photoreceptor and electrophotographic device with same |
| KR20130051321A (en) * | 2011-11-09 | 2013-05-20 | (주)위델소재 | Novel tetiary aryl amine and organic electroluminescent device using the same |
| KR20130120855A (en) * | 2012-04-26 | 2013-11-05 | (주)위델소재 | Using thiophen derivative as hole transporting mateial and organic electroluminescent device using the same |
| KR20160027940A (en) * | 2014-09-02 | 2016-03-10 | 주식회사 엘지화학 | Organic light emitting device |
| CN106478592A (en) * | 2015-08-28 | 2017-03-08 | 三星显示有限公司 | Fused ring compound and the organic light emitting apparatus including which |
| CN107235899A (en) * | 2017-07-13 | 2017-10-10 | 长春海谱润斯科技有限公司 | A kind of new acridine compound and its organic luminescent device |
-
2018
- 2018-06-11 CN CN201810598646.2A patent/CN108976166A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07281464A (en) * | 1994-04-08 | 1995-10-27 | Canon Inc | Electrophotographic photoreceptor and electrophotographic device with same |
| KR20130051321A (en) * | 2011-11-09 | 2013-05-20 | (주)위델소재 | Novel tetiary aryl amine and organic electroluminescent device using the same |
| KR20130120855A (en) * | 2012-04-26 | 2013-11-05 | (주)위델소재 | Using thiophen derivative as hole transporting mateial and organic electroluminescent device using the same |
| KR20160027940A (en) * | 2014-09-02 | 2016-03-10 | 주식회사 엘지화학 | Organic light emitting device |
| CN106478592A (en) * | 2015-08-28 | 2017-03-08 | 三星显示有限公司 | Fused ring compound and the organic light emitting apparatus including which |
| CN107235899A (en) * | 2017-07-13 | 2017-10-10 | 长春海谱润斯科技有限公司 | A kind of new acridine compound and its organic luminescent device |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109824522A (en) * | 2019-03-29 | 2019-05-31 | 吉林奥来德光电材料股份有限公司 | A kind of organic luminescent compounds and its preparation method and application |
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