CN111253374A - Naphtho five-membered ring benzo fused heterocycle organic compound and application thereof - Google Patents
Naphtho five-membered ring benzo fused heterocycle organic compound and application thereof Download PDFInfo
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- CN111253374A CN111253374A CN202010242536.XA CN202010242536A CN111253374A CN 111253374 A CN111253374 A CN 111253374A CN 202010242536 A CN202010242536 A CN 202010242536A CN 111253374 A CN111253374 A CN 111253374A
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- Prior art keywords
- substituted
- organic compound
- unsubstituted
- dibenzothienyl
- aza
- Prior art date
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- Pending
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- -1 heterocycle organic compound Chemical class 0.000 title claims abstract description 42
- 125000005605 benzo group Chemical group 0.000 title claims abstract description 7
- 239000000463 material Substances 0.000 claims abstract description 36
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 14
- 239000010410 layer Substances 0.000 claims description 43
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 20
- 125000005561 phenanthryl group Chemical group 0.000 claims description 15
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 10
- 235000010290 biphenyl Nutrition 0.000 claims description 10
- 239000004305 biphenyl Substances 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims description 9
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000001769 aryl amino group Chemical group 0.000 claims description 8
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 8
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 8
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 8
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 125000004306 triazinyl group Chemical group 0.000 claims description 8
- 125000005580 triphenylene group Chemical group 0.000 claims description 8
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 7
- 239000012044 organic layer Substances 0.000 claims description 7
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 5
- 125000005493 quinolyl group Chemical group 0.000 claims description 5
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 4
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims 1
- 239000007787 solid Substances 0.000 abstract description 29
- 150000001875 compounds Chemical class 0.000 abstract description 11
- 238000002360 preparation method Methods 0.000 abstract description 5
- 238000009825 accumulation Methods 0.000 abstract description 4
- 230000002349 favourable effect Effects 0.000 abstract description 4
- 230000009286 beneficial effect Effects 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 230000003321 amplification Effects 0.000 abstract description 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
- 238000013508 migration Methods 0.000 abstract description 2
- 230000005012 migration Effects 0.000 abstract description 2
- 238000003199 nucleic acid amplification method Methods 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 61
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
- 238000001704 evaporation Methods 0.000 description 22
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- 239000012074 organic phase Substances 0.000 description 16
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 14
- 239000012295 chemical reaction liquid Substances 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 230000008020 evaporation Effects 0.000 description 10
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- 239000000243 solution Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 238000002347 injection Methods 0.000 description 9
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 8
- 239000011521 glass Substances 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000001308 synthesis method Methods 0.000 description 5
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 5
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 4
- SFKMVPQJJGJCMI-UHFFFAOYSA-N 2-chloro-4-phenylquinazoline Chemical compound C=12C=CC=CC2=NC(Cl)=NC=1C1=CC=CC=C1 SFKMVPQJJGJCMI-UHFFFAOYSA-N 0.000 description 4
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000011368 organic material Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- SFUIGUOONHIVLG-UHFFFAOYSA-N (2-nitrophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1[N+]([O-])=O SFUIGUOONHIVLG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 2
- 239000005751 Copper oxide Substances 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 101000766357 Ruditapes philippinarum Big defensin Proteins 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 229910000431 copper oxide Inorganic materials 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- YDMRDHQUQIVWBE-UHFFFAOYSA-N (2-hydroxyphenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1O YDMRDHQUQIVWBE-UHFFFAOYSA-N 0.000 description 1
- HTFNVAVTYILUCF-UHFFFAOYSA-N 2-[2-ethoxy-4-[4-(4-methylpiperazin-1-yl)piperidine-1-carbonyl]anilino]-5-methyl-11-methylsulfonylpyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical compound CCOc1cc(ccc1Nc1ncc2N(C)C(=O)c3ccccc3N(c2n1)S(C)(=O)=O)C(=O)N1CCC(CC1)N1CCN(C)CC1 HTFNVAVTYILUCF-UHFFFAOYSA-N 0.000 description 1
- PWOBDMNCYMQTCE-UHFFFAOYSA-N 2-chlorobenzenethiol Chemical compound SC1=CC=CC=C1Cl PWOBDMNCYMQTCE-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 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
- 239000010405 anode material Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229930192474 thiophene Natural products 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
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
-
- 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
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
- C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
- C07D491/153—Ortho-condensed systems the condensed system containing two rings with oxygen as ring hetero atom and one ring with nitrogen as ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/14—Ortho-condensed systems
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- 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
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Abstract
The invention belongs to the technical field of organic photoelectric materials, and particularly relates to a naphtho five-membered ring benzo fused heterocycle organic compound and application thereof. The organic compound has a parent structure of a naphtho five-membered ring fused benzo heterocycle, has high bond energy among atoms, has good thermal stability, is favorable for intermolecular solid accumulation, and can effectively prolong the service life of the material when used as a luminescent layer material. The compound is a large conjugated fused heterocyclic derivative, is applied in a light-emitting layer, has a proper energy level with an adjacent layer, is favorable for injecting holes and electrons, can effectively reduce the starting voltage, and can realize good luminous efficiency in a device at a higher exciton migration rate. The compound has a larger conjugated plane, is beneficial to molecular accumulation, shows good thermodynamic stability and shows long service life in a device. The preparation process of the derivative is simple and easy to implement, the raw materials are easy to obtain, and the preparation method is suitable for mass production and amplification.
Description
Technical Field
The invention belongs to the technical field of organic photoelectric materials, and particularly relates to a naphtho five-membered ring benzo fused heterocycle organic compound and application thereof.
Background
Electroluminescence (EL) refers to a phenomenon in which a light emitting material emits light when excited by an electric current and an electric field under the action of an electric field, and is a light emitting process in which electric energy is directly converted into light energy. The organic electroluminescent display (hereinafter referred to as OLED) has a series of advantages of self-luminescence, low-voltage dc driving, full curing, wide viewing angle, light weight, simple composition and process, etc., and compared with the liquid crystal display, the organic electroluminescent display does not need a backlight source, and has a large viewing angle, low power, a response speed 1000 times that of the liquid crystal display, and a manufacturing cost lower than that of the liquid crystal display with the same resolution. Therefore, the organic electroluminescent device has very wide application prospect.
With the continuous advance of the OLED technology in the two fields of lighting and display, people pay more attention to the research on efficient organic materials affecting the performance of OLED devices, and an organic electroluminescent device with good efficiency and long service life is generally the result of the optimized matching of device structures and various organic materials, which provides great opportunities and challenges for chemists to design and develop functional materials with various structures.
Organic electroluminescent materials have many advantages over inorganic luminescent materials, such as: the processing performance is good, a film can be formed on any substrate by an evaporation or spin coating method, and flexible display and large-area display can be realized; the optical property, the electrical property, the stability and the like of the material can be adjusted by changing the structure of molecules, and the selection of the material has a large space. In the most common OLED device structures, the following classes of organic materials are typically included: hole injection materials, hole transport materials, electron transport materials, and light emitting materials (dyes or doped guest materials) and corresponding host materials of each color. The phosphorescent host materials used at present often have single carrier transport capability, such as hole-based transport hosts and electron-based transport hosts, but the single carrier transport capability may cause mismatching of electrons and holes in the light emitting layer, thereby causing severe efficiency roll-off and shortened lifetime.
Although CN108290875A discloses a bulk structure of a thick hetero thiophene, it can only be used as a dual-host material due to the unbalanced carrier transport.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides a naphtho five-membered ring benzo fused heterocycle organic compound and application thereof.
The technical scheme for solving the technical problems is as follows: a naphtho five-membered ring benzo fused heterocycle organic compound has a structural formula as follows:
wherein R is1-R8Each independently is hydrogen, C1-C10Alkyl radical, C1-C6Cycloalkyl, substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C3-C30Any one of heteroaryl;
Z1、Z2、Y1each independently is a chemical bond, O, S, CR9R10Or NR11And at least one is NR11At least one is not a chemical bond; y is2Is a chemical bond, O, S or CR9R10；
R9、R10Each independently is C1-C10Alkyl radical, C1-C6Cycloalkyl, substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C3-C30Any one of heteroaryl; r11Is substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C3-C30A heteroaryl group;
x is O, S or CR12R13；R12、R13Each independently is C1-C10Alkyl radical, C1-C6Cycloalkyl, substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C3-C30A heteroaryl group.
Further, R1-R13Wherein the substituents of the selected groups are each independently hydrogen, halogen, nitro, cyano, C1-C4Alkyl, phenyl, biphenyl, terphenyl, or naphthyl.
Further, R1-R8Each independently is hydrogen, deuterium, methyl, ethyl, cyclopentyl, cyclohexyl, substituted or unsubstituted phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furanyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, phenanthryl, 9-dimethylfluorenyl, spirofluorenyl, arylamino, or carbazolyl.
Further, R9、R10Each independently is methyl, ethyl, cyclopentylCyclohexyl, substituted or unsubstituted phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furyl, benzofuryl, dibenzofuryl, aza-dibenzofuryl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, phenanthryl, 9-dimethylfluorenyl, spirofluorenyl, arylamino, or carbazolyl.
Further, R11Is a substituted or unsubstituted phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furyl, benzofuryl, dibenzofuryl, aza-dibenzofuryl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, phenanthryl, 9-dimethylfluorenyl, spirofluorenyl, arylamino, or carbazole group.
Further, R12、R13Each independently is methyl, ethyl, cyclopentyl, cyclohexyl, substituted or unsubstituted phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furanyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, phenanthryl, 9-dimethylfluorenyl, spirofluorenyl, arylamino, or carbazolyl.
Further, R1-R8In (b), any two adjacent groups are linked to form a ring by a chemical bond.
Further, the structural formula of the above organic compound is as follows:
the second object of the present invention is to provide the use of the above organic compounds in organic electroluminescent devices.
An organic electroluminescent device comprises a substrate, an anode layer, an organic layer at least comprising a light-emitting layer, and a cathode layer sequentially formed on the substrate; the organic layer comprises an organic light-emitting layer, and the host material of the organic light-emitting layer comprises at least one organic compound.
The invention has the beneficial effects that:
the organic compound has a parent structure of a naphtho five-membered ring fused benzo heterocycle, has high bond energy among atoms, has good thermal stability, is favorable for intermolecular solid accumulation, and can effectively prolong the service life of the material when used as a luminescent layer material. The compound is a large conjugated fused heterocyclic derivative, is applied in a light-emitting layer, has a proper energy level with an adjacent layer, is favorable for injecting holes and electrons, can effectively reduce the starting voltage, and can realize good luminous efficiency in a device at a higher exciton migration rate. The compound has a larger conjugated plane, is beneficial to molecular accumulation, shows good thermodynamic stability and shows long service life in a device. The preparation process of the derivative is simple and easy to implement, the raw materials are easy to obtain, and the preparation method is suitable for mass production and amplification.
Detailed Description
The principles and features of this invention are described below in conjunction with examples which are set forth to illustrate, but are not to be construed to limit the scope of the invention.
Example 1
Synthesis of Compound A1, the reaction equation is as follows:
the synthesis method comprises the following steps:
(1) 5-bromonaphthobenzothiophene (100mmol), o-hydroxyphenylboronic acid (110mmol) and (1 percent) are added into a reaction bottlePd(PPh3)4Heating 40g (300mmol) of sodium carbonate, 800mL of toluene, 200mL of ethanol and 200mL of water to reflux, and reacting for 8 hours to finish the reaction; extracting the reaction liquid by ethyl acetate, and concentrating an organic phase to obtain a yellow solid M1;
(2) adding (100mmol) intermediate M1 into 1000mL DMF solution, adding (300mmol) copper oxide and (300mmol) potassium carbonate, heating to reflux, reacting for 12h, and finishing the reaction; evaporating to remove solvent, performing silica gel column chromatography, and separating to obtain intermediate M2;
(3) dissolving (100mmol) M2 in 500mL THF, adding (120mmol) butyl lithium at-78 deg.C, stirring under controlled temperature, reacting for 1h, dropwise adding dibromoethane (120mmol), and reacting for 12 h; adding water into the reaction solution, extracting with ethyl acetate, concentrating the organic phase, separating out solids, and filtering to obtain a white solid M3;
(4) adding (100mmol) M3, (110mmol) o-chloroaniline, (1%) Pd (dba), tri-tert-butylphosphine (1%), sodium tert-butoxide 40g (300mmol) and toluene 800mL into a reaction bottle, heating to reflux, reacting for 8h, and adding water after the reaction is finished; extracting the reaction liquid by ethyl acetate, and concentrating an organic phase to obtain a yellow solid M4;
(5) adding (100mmol) intermediate M4 into 1000mL DMAC, continuing to add (5%) Pd (OAC), (300mmol) tricyclohexylphosphine and 40g potassium carbonate (300mmol), heating to reflux, reacting for 12h, and finishing the reaction; evaporating to remove solvent, performing silica gel column chromatography, and separating to obtain intermediate M5;
(6) adding (100mmol) intermediate M5, 2-chloro-4-phenylquinazoline (100mmol), potassium carbonate 40g (300mmol) and 1000mL DMF in a reaction flask, and reacting at 120 ℃ for 12 h; after the reaction was complete, the reaction was stopped and the reaction was cooled to room temperature, water was added, filtered, washed with water and the resulting solid was purified by recrystallization from toluene to give a yellow powder a 1.
1H NMR(400MHz,Chloroform)δ8.55(d,J＝6.4Hz,3H),8.15–7.84(m,3H),7.84–7.72(m,4H),7.63(d,J＝10.0Hz,2H),7.59–7.59(m,5H),7.52 7.39-7.16(m,6H)。
Example 2
Synthesis of Compound A5, the reaction equation is as follows:
the synthesis method comprises the following steps:
(1) the reaction flask is added with (100mmol) 5-bromonaphthobenzothiophene, (110mmol) o-nitrobenzeneboronic acid and (1%) Pd (PPh)3)4Heating 40g (300mmol) of sodium carbonate, 800mL of toluene, 200mL of ethanol and 200mL of water to reflux, and reacting for 8 hours to finish the reaction; extracting the reaction liquid by ethyl acetate, and concentrating an organic phase to obtain a yellow solid M1;
(2) adding (100mmol) intermediate M1 into 1000ml o-dichlorobenzene solution, adding (300mmol) triphenylphosphine, heating to reflux, reacting for 12h, and finishing the reaction; evaporating to remove solvent, performing silica gel column chromatography, and separating to obtain intermediate M2;
(3) adding (100mmol) M2, (110mmol) iodobenzene, (1%) Pd (dba), (1%) S-Phos, 40g (300mmol) of sodium tert-butoxide and 800mL of xylene into a reaction bottle, heating to reflux, and reacting for 8 h; extracting the reaction liquid by ethyl acetate, and concentrating an organic phase to obtain a yellow solid M3;
(4) dissolving (100mmol) M3 in 500mL THF, adding (120mmol) butyl lithium at-78 deg.C, stirring under controlled temperature, reacting for 1h, dropwise adding dibromoethane (120mmol), and reacting for 12 h; adding water into the reaction solution, extracting with ethyl acetate, concentrating the organic phase, separating out solids, and filtering to obtain yellow solid M4;
(5) adding (100mmol) M4, (110mmol) o-chloroaniline, (1%) Pd (dba), tri-tert-butylphosphine (1%), sodium tert-butoxide 40g (300mmol) and toluene 800mL into a reaction bottle, heating to reflux, reacting for 8h, and adding water after the reaction is finished; extracting the reaction liquid by ethyl acetate, and concentrating an organic phase to obtain a yellow solid M5;
(6) adding (100mmol) intermediate M5 into 1000ml DMAC, continuing to add (5%) Pd (OAC), (300mmol) tricyclohexylphosphine and 40g potassium carbonate (300mmol), heating to reflux, reacting for 12h, and finishing the reaction; evaporating to remove solvent, performing silica gel column chromatography, and separating to obtain intermediate M6;
(7) adding (100mmol) intermediate M6, 2-chloro-4-phenylquinazoline (100mmol), potassium carbonate 40g (300mmol) and 1000mL DMF in a reaction flask, and reacting at 120 ℃ for 12 h; after the reaction was complete, the reaction was stopped and the reaction was cooled to room temperature, water was added, filtered, washed with water and the resulting solid was purified by recrystallization from toluene to give a yellow powder a 5.
1H NMR(CDCl3,400MHz)δ8.55(d,J＝8.0Hz,3H),8.05(d,J＝10.4Hz,3H),7.96–7.77(m,7H),7.76(s,1H),7.72–7.45(m,8H),7.33-7.15(m,6H)。
Example 3
Synthesis of Compound A10, the reaction equation is as follows:
the synthesis method comprises the following steps:
(1) the reaction flask was charged with (100mmol) 5-bromonaphthobenzofuran, (110mmol) o-nitrobenzeneboronic acid, (1%) Pd (PPh)3)4Heating 40g (300mmol) of sodium carbonate, 800mL of toluene, 200mL of ethanol and 200mL of water to reflux, and reacting for 8 hours to finish the reaction; extracting the reaction liquid by ethyl acetate, and concentrating an organic phase to obtain a yellow solid M1;
(2) adding (100mmol) intermediate M1 into 1000ml o-dichlorobenzene solution, adding (300mmol) triphenylphosphine, heating to reflux, reacting for 12h, and finishing the reaction; evaporating to remove solvent, performing silica gel column chromatography, and separating to obtain intermediate M2;
(3) adding (100mmol) M2, (110mmol) iodobenzene, (1%) Pd (dba), (1%) S-Phos, 40g (300mmol) of sodium tert-butoxide and 800mL of xylene into a reaction bottle, heating to reflux, and reacting for 8 h; extracting the reaction liquid by ethyl acetate, and concentrating an organic phase to obtain a yellow solid M3;
(4) dissolving (100mmol) M3 in 500mL THF, adding (120mmol) butyl lithium at-78 deg.C, stirring under controlled temperature, reacting for 1h, dropwise adding dibromoethane (120mmol), and reacting for 12 h; adding water into the reaction solution, extracting with ethyl acetate, concentrating the organic phase, separating out solids, and filtering to obtain yellow solid M4;
(5) adding (100mmol) M4, (110mmol) o-chloroaniline, (1%) Pd (dba), tri-tert-butylphosphine (1%), sodium tert-butoxide 40g (300mmol) and toluene 800mL into a reaction bottle, heating to reflux, reacting for 8h, and adding water after the reaction is finished; extracting the reaction liquid by ethyl acetate, and concentrating an organic phase to obtain a yellow solid M5;
(6) adding (100mmol) intermediate M5 into 1000ml DMAC, continuing to add (5%) Pd (OAC), (300mmol) tricyclohexylphosphine and 40g potassium carbonate (300mmol), heating to reflux, reacting for 12h, and finishing the reaction; evaporating to remove solvent, performing silica gel column chromatography, and separating to obtain intermediate M6;
(7) adding (100mmol) intermediate M6, 2-chloro-4-phenylquinazoline (100mmol), potassium carbonate 40g (300mmol) and 1000mL DMF in a reaction flask, and reacting at 120 ℃ for 12 h; after the reaction was complete, the reaction was stopped and the reaction was cooled to room temperature, water was added, filtered, washed with water and the resulting solid was purified by recrystallization from toluene to give a yellow powder a 10.
1H NMR(CDCl3,400MHz)δ8.55(d,J＝8.0Hz,2H),8.05(d,J＝10.0Hz,2H),7.96–7.77(m,8H),7.76(s,1H),7.72–7.45(m,9H),7.33-7.15(m,6H)。
Example 4
Synthesis of Compound A17, the reaction equation is as follows:
the synthesis method comprises the following steps:
(1) adding 100mmol of 5-bromonaphthobenzothiophene, 110mmol of o-mercaptochlorobenzene, 40g (300mmol) of sodium carbonate and 800mL of toluene into a reaction bottle, heating to reflux, and reacting for 8 hours to finish the reaction; extracting the reaction liquid by ethyl acetate, and concentrating an organic phase to obtain a yellow solid M1;
(2) adding (100mmol) intermediate M1 into 1000ml DMAC, continuing to add (5%) Pd (OAC), (300mmol) tricyclohexylphosphine and 40g potassium carbonate (300mmol), heating to reflux, reacting for 12h, and finishing the reaction; evaporating to remove solvent, performing silica gel column chromatography, and separating to obtain intermediate M2;
(3) dissolving (100mmol) M2 in 500mL THF, adding (120mmol) butyl lithium at-78 deg.C, stirring under controlled temperature, reacting for 1h, dropwise adding dibromoethane (120mmol), and reacting for 12 h; adding water into the reaction solution, extracting with ethyl acetate, concentrating the organic phase, separating out solids, and filtering to obtain yellow solid M3;
(4) adding (100mmol) M3, (110mmol) o-chloroaniline, (1%) Pd (dba), tri-tert-butylphosphine (1%), sodium tert-butoxide 40g (300mmol) and toluene 800mL into a reaction bottle, heating to reflux, reacting for 8h, and adding water after the reaction is finished; extracting the reaction liquid by ethyl acetate, and concentrating an organic phase to obtain a yellow solid M4;
(6) adding (100mmol) intermediate M4 into 1000ml DMAC, continuing to add (5%) Pd (OAC), (300mmol) tricyclohexylphosphine and 40g potassium carbonate (300mmol), heating to reflux, reacting for 12h, and finishing the reaction; evaporating to remove solvent, performing silica gel column chromatography, and separating to obtain intermediate M5;
(7) adding (100mmol) intermediate M5, 2-chloro-4-phenylquinazoline (100mmol), potassium carbonate 40g (300mmol) and 1000mL DMF in a reaction flask, and reacting at 120 ℃ for 12 h; after the reaction was complete, the reaction was stopped and the reaction was cooled to room temperature, water was added, filtered, washed with water and the resulting solid was purified by recrystallization from toluene to give a yellow powder a 17.
1H NMR(CDCl3,400MHz)：8.55(d,J＝8.0Hz,1H),8.14(d,J＝12.0Hz,2H),8.04-7.87(m,3H),7.87–7.74(m,4H),7.70–7.59(m,6H),7.53(dd,J＝13.2,8.8Hz,2H),7.32(d,J＝10.0Hz,2H),7.16-7.11(m,3H).
Example 5
Synthesis of Compound A30, the reaction equation is as follows:
the synthesis method comprises the following steps:
(1) 5-bromonaphthobenzothiophene (100mmol), o-nitrobenzeneboronic acid (110mmol) and Pd (1%) in a reaction bottle (PPh)3)4Heating 40g (300mmol) of sodium carbonate, 800mL of toluene, 200mL of ethanol and 200mL of water to reflux, and reacting for 8 hours to finish the reaction; extracting the reaction liquid by ethyl acetate, and concentrating an organic phase to obtain a yellow solid M1;
(2) adding (100mmol) intermediate M1 into 1000mL of o-dichlorobenzene solution, adding (300mmol) triphenylphosphine, heating to reflux, reacting for 12h, and finishing the reaction; evaporating to remove solvent, performing silica gel column chromatography, and separating to obtain intermediate M2;
(3) adding (100mmol) intermediate M2, 2-chloro-5-cyano-1, 3-pyrimidine (100mmol), potassium carbonate 40g (300mmol) and 1000mL DMF in a reaction bottle, and reacting at 120 ℃ for 12 h; stopping the reaction after the reaction is finished, cooling the reactant to room temperature, adding water, filtering, washing with water, and recrystallizing and purifying the obtained solid in toluene to obtain yellow powder M3;
(4) dissolving (100mmol) M3 in 500mL dichloromethane, adding (100mmol) NBS in batches at 0 ℃, stirring at normal temperature, and reacting for 8 h; adding water into the reaction solution, separating out solids, and filtering to obtain a yellow solid M4;
(5) adding (100mmol) M4, (110mmol) o-chlorophenol, sodium tert-butoxide 40g (300mmol) and DMF 500mL into a reaction bottle, heating to reflux, reacting for 8h, and adding water after the reaction is finished; extracting the reaction liquid by ethyl acetate, and concentrating an organic phase to obtain a yellow solid M5;
(6) adding (100mmol) intermediate M5 into 1000mL DMF solution, adding (300mmol) copper oxide and (300mmol) potassium carbonate, heating to reflux, reacting for 12h, and finishing the reaction; evaporating to remove solvent, performing silica gel column chromatography, and separating to obtain A30.
1H NMR(CDCl3,400MHz)δ9.59(s,2H),8.55(d,J＝8.0Hz,2H),7.98(m,2H),7.70(d,J＝8.4Hz,3H),7.53(d,J＝10.0Hz,2H),7.32(d,J＝10.0Hz,2H),7.16-7.11(m,3H)。
The other compounds of the present invention can be synthesized by selecting raw materials with suitable structures according to the above-mentioned ideas of examples 1-5, and the synthesis process is not repeated here.
Device application example
The OLED includes first and second electrodes on a substrate, and an organic layer between the electrodes. The organic layer may in turn be divided into a plurality of regions. For example, the organic layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. The substrate is a conventional substrate used in an organic light emitting display in the related art, for example, glass, polymer materials, glass and polymer materials with TFT components, and the like.
The anode material may be Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO) known in the art2) Transparent conductive materials such as zinc oxide (ZnO), metal materials such as silver and its alloys, aluminum and its alloys, organic conductive materials such as PEDOT, and multilayer structures of these materials.
The cathode material can be selected from materials and structures such as, but not limited to, magnesium silver mixture, metal such as LiF/Al, ITO, etc., metal mixture, oxide, etc.
The OLED device can also comprise a hole injection layer and a hole transport layer which are positioned between the light-emitting layer and the anode, and the layers can be but are not limited to compounds shown in HT-1 to HT-31 below; or any combination thereof.
The device light emitting layer may comprise a host material and a light emitting dye, wherein the host material includes, but is not limited to, one or more combinations of conventional materials as shown in GPH1-GPH80 below.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light emitting layer thereof may be selected from, but not limited to, a combination of one or more of RPD-1 to RPD-28 listed below.
In one aspect of the invention, the electron transport layer material may be selected from, but is not limited to, the combination of one or more of ET-1 through ET-57 listed below.
An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, combinations of one or more of the following: LiQ, LiF, NaCl, CsF, Li2O,Cs2CO3,BaO,Na,Li,Ca。
The effects of the compounds obtained in examples 1 to 6 of the present invention and the comparative product R1 as host materials for light-emitting layers in devices are described in detail by performance tests below.
The preparation processes of the organic electroluminescent devices described in application examples 1 to 6 and comparative example 1 of the present invention were as follows:
(1) ultrasonically treating the glass plate coated with the ITO transparent conducting layer in a commercial cleaning agent, washing the glass plate in deionized water, ultrasonically removing oil in an acetone-ethanol mixed solvent, baking the glass plate in a clean environment until the water is completely removed, cleaning the glass plate by using ultraviolet light and ozone, and bombarding the surface by using low-energy solar beams;
(2) placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to less than 1 × 10-5Pa, vacuum evaporating HT-11 on the anode layer film to form a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10 nm;
(3) evaporating HT-5 on the hole injection layer in vacuum to serve as a hole transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 80 nm;
(4) the light-emitting layer of the device is evaporated on the hole transport layer in vacuum, the light-emitting layer comprises a main material and a dye material, the main material is A1, A5, A10, A17, A26, A30 and R1 respectively used by a multi-source co-evaporation method, the evaporation rate of the main material is adjusted to be 0.1nm/s, the proportion of 3% of the evaporation rate of the dye RPD-1 is set, and the total thickness of the evaporation film is 30 nm;
(5) an electron transport layer of the device is vacuum evaporated on the light emitting layer, and the material ET-42 is selected, the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 30 nm;
(6) LiF with the thickness of 0.5nm is vacuum-evaporated on the Electron Transport Layer (ETL) to be used as an electron injection layer, and an Al layer with the thickness of 150nm is used as a cathode of the device.
The organic electroluminescent device prepared by the above process was subjected to the following performance measurement:
the organic electroluminescent devices prepared in application examples 1 to 6 and comparative example 1 were measured for driving voltage, current efficiency and lifetime at the same luminance using a digital source meter and a luminance meter, and specifically, the luminance of the organic electroluminescent device reached 5000cd/m, as measured by increasing the voltage at a rate of 0.1V/sec2The current density is measured at the same time as the driving voltage; the ratio of the brightness to the current density is the current efficiency; the life test of LT95 is as follows: using a luminance meter at 5000cd/m2The luminance drop of the organic electroluminescent device was measured to be 4750cd/m by maintaining a constant current at luminance2Time in hours, the results are shown in table 1 below.
TABLE 1
As can be seen from the data in Table 1, the novel organic material prepared by the invention is used as a main material of an organic electroluminescent device, can effectively reduce the rise-fall voltage, improve the current efficiency and prolong the service life of the device, and is a main material with good performance.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (10)
1. A naphtho five-membered ring benzo fused heterocycle organic compound is characterized by having a structural formula as follows:
wherein R is1-R8Each independently is hydrogen, C1-C10Alkyl radical, C1-C6Cycloalkyl, substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C3-C30Any one of heteroaryl;
Z1、Z2、Y1each independently is a chemical bond, O, S, CR9R10Or NR11And at least one is NR11At least one is not a chemical bond; y is2Is a chemical bond, O, S or CR9R10；
R9、R10Each independently is C1-C10Alkyl radical, C1-C6Cycloalkyl, substituted or unsubstituted C6-C30Aryl or substituted orUnsubstituted C3-C30Any one of heteroaryl; r11Is substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C3-C30A heteroaryl group;
x is O, S or CR12R13；R12、R13Each independently is C1-C10Alkyl radical, C1-C6Cycloalkyl, substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C3-C30A heteroaryl group.
2. An organic compound according to claim 1, wherein R is1-R13Wherein the substituents of the selected groups are each independently hydrogen, halogen, nitro, cyano, C1-C4Alkyl, phenyl, biphenyl, terphenyl, or naphthyl.
3. An organic compound according to claim 1, wherein R is1-R8Each independently is hydrogen, deuterium, methyl, ethyl, cyclopentyl, cyclohexyl, substituted or unsubstituted phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furanyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, phenanthryl, 9-dimethylfluorenyl, spirofluorenyl, arylamino, or carbazolyl.
4. An organic compound according to claim 1, wherein R is9、R10Each independently is methyl, ethyl, cyclopentyl, cyclohexyl, substituted or unsubstituted phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinylCinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furyl, benzofuryl, dibenzofuryl, aza-dibenzofuryl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, phenanthrenyl, 9-dimethylfluorenyl, spirofluorenyl, arylamino or carbazolyl.
5. An organic compound according to claim 1, wherein R is11Is a substituted or unsubstituted phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furyl, benzofuryl, dibenzofuryl, aza-dibenzofuryl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, phenanthryl, 9-dimethylfluorenyl, spirofluorenyl, arylamino, or carbazole group.
6. An organic compound according to claim 1, wherein R is12、R13Each independently is methyl, ethyl, cyclopentyl, cyclohexyl, substituted or unsubstituted phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furanyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, phenanthryl, 9-dimethylfluorenyl, spirofluorenyl, arylamino, or carbazolyl.
7. An organic compound according to claim 1, wherein R is1-R8In (b), any two adjacent groups are linked to form a ring by a chemical bond.
8. An organic compound according to claim 1, having the formula:
9. use of an organic compound according to any one of claims 1 to 8 in an organic electroluminescent device.
10. An organic electroluminescent device comprises a substrate, an anode layer, an organic layer at least comprising a light-emitting layer, and a cathode layer sequentially formed on the substrate; characterized in that the organic layer comprises an organic light-emitting layer, the host material of which comprises at least one organic compound according to any one of claims 1 to 8.
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| CN111909171A (en) * | 2020-07-31 | 2020-11-10 | 北京燕化集联光电技术有限公司 | Novel electronic transmission material and application thereof |
| CN111909172A (en) * | 2020-07-31 | 2020-11-10 | 北京燕化集联光电技术有限公司 | Novel oxygen-containing multi-heterocyclic compound and application thereof |
| CN111961063A (en) * | 2020-07-31 | 2020-11-20 | 北京燕化集联光电技术有限公司 | Oxygen-containing multi-heterocyclic compound and application thereof |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111909171A (en) * | 2020-07-31 | 2020-11-10 | 北京燕化集联光电技术有限公司 | Novel electronic transmission material and application thereof |
| CN111909172A (en) * | 2020-07-31 | 2020-11-10 | 北京燕化集联光电技术有限公司 | Novel oxygen-containing multi-heterocyclic compound and application thereof |
| CN111961063A (en) * | 2020-07-31 | 2020-11-20 | 北京燕化集联光电技术有限公司 | Oxygen-containing multi-heterocyclic compound and application thereof |
| CN111961063B (en) * | 2020-07-31 | 2022-11-11 | 北京燕化集联光电技术有限公司 | Oxygen-containing multi-heterocyclic compound and application thereof |
| CN111909171B (en) * | 2020-07-31 | 2022-12-09 | 北京燕化集联光电技术有限公司 | Electron transport material and application thereof |
| CN111909172B (en) * | 2020-07-31 | 2022-12-13 | 北京燕化集联光电技术有限公司 | Oxygen-containing multi-heterocyclic compound and application thereof |
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