CN115724825A - Acridine phenyl phenanthroimidazole compound for preparing luminescent layer of electroluminescent device and preparation method thereof - Google Patents
Acridine phenyl phenanthroimidazole compound for preparing luminescent layer of electroluminescent device and preparation method thereof Download PDFInfo
- Publication number
- CN115724825A CN115724825A CN202210939882.2A CN202210939882A CN115724825A CN 115724825 A CN115724825 A CN 115724825A CN 202210939882 A CN202210939882 A CN 202210939882A CN 115724825 A CN115724825 A CN 115724825A
- Authority
- CN
- China
- Prior art keywords
- phenyl
- acridine
- compound
- phenanthroimidazole
- halogenated
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 Acridine phenyl phenanthroimidazole compound Chemical class 0.000 title claims abstract description 58
- 238000002360 preparation method Methods 0.000 title claims description 9
- 239000000463 material Substances 0.000 claims abstract description 37
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- DZBUGLKDJFMEHC-UHFFFAOYSA-N benzoquinolinylidene Natural products C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000002994 raw material Substances 0.000 claims abstract description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 10
- 238000009833 condensation Methods 0.000 claims description 9
- 230000005494 condensation Effects 0.000 claims description 9
- 238000007363 ring formation reaction Methods 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 230000003197 catalytic effect Effects 0.000 claims description 7
- 238000005859 coupling reaction Methods 0.000 claims description 7
- ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical group BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 5
- 239000008096 xylene Substances 0.000 claims description 5
- ATTVYRDSOVWELU-UHFFFAOYSA-N 1-diphenylphosphoryl-2-(2-diphenylphosphorylphenoxy)benzene Chemical compound C=1C=CC=CC=1P(C=1C(=CC=CC=1)OC=1C(=CC=CC=1)P(=O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(=O)C1=CC=CC=C1 ATTVYRDSOVWELU-UHFFFAOYSA-N 0.000 claims description 4
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 4
- 239000005695 Ammonium acetate Substances 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 229940043376 ammonium acetate Drugs 0.000 claims description 4
- 235000019257 ammonium acetate Nutrition 0.000 claims description 4
- 239000012295 chemical reaction liquid Substances 0.000 claims description 4
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 claims description 3
- NAIGXIXEPKSMBJ-UHFFFAOYSA-N 2-phenyl-1h-naphtho[2,1-e]benzimidazole Chemical class C1=CC=CC=C1C(N1)=NC2=C1C=CC1=C2C=CC2=CC=CC=C12 NAIGXIXEPKSMBJ-UHFFFAOYSA-N 0.000 claims description 3
- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 claims description 3
- 150000001251 acridines Chemical class 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 claims description 2
- NIEBHDXUIJSHSL-UHFFFAOYSA-N 4-iodobenzaldehyde Chemical compound IC1=CC=C(C=O)C=C1 NIEBHDXUIJSHSL-UHFFFAOYSA-N 0.000 claims description 2
- 239000003929 acidic solution Substances 0.000 claims description 2
- 239000003849 aromatic solvent Substances 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000005453 ketone based solvent Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- GZPPANJXLZUWHT-UHFFFAOYSA-N 1h-naphtho[2,1-e]benzimidazole Chemical compound C1=CC2=CC=CC=C2C2=C1C(N=CN1)=C1C=C2 GZPPANJXLZUWHT-UHFFFAOYSA-N 0.000 abstract description 4
- 230000005284 excitation Effects 0.000 abstract description 4
- 239000011159 matrix material Substances 0.000 abstract description 2
- 238000002347 injection Methods 0.000 description 18
- 239000007924 injection Substances 0.000 description 18
- 238000001704 evaporation Methods 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 230000005525 hole transport Effects 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 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 6
- 230000003111 delayed effect Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 238000002189 fluorescence spectrum Methods 0.000 description 4
- 238000004020 luminiscence type Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 4
- 238000002411 thermogravimetry Methods 0.000 description 4
- 238000002211 ultraviolet spectrum Methods 0.000 description 4
- 229910015711 MoOx Inorganic materials 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000001194 electroluminescence spectrum Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 3
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 3
- 150000002940 palladium Chemical class 0.000 description 3
- 238000007747 plating Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 125000005594 diketone group Chemical group 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 2
- 150000002941 palladium compounds Chemical class 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QTPLEVOKSWEYAC-UHFFFAOYSA-N 1,2-diphenyl-9h-fluorene Chemical compound C=1C=CC=CC=1C1=C2CC3=CC=CC=C3C2=CC=C1C1=CC=CC=C1 QTPLEVOKSWEYAC-UHFFFAOYSA-N 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 description 1
- DYBJFUXHRFXNMX-UHFFFAOYSA-N 2-(4-bromophenyl)-3-(4-methoxyphenyl)phenanthro[9,10-d]imidazole Chemical compound C1=CC(OC)=CC=C1N1C(C=2C(=CC=CC=2)C=2C3=CC=CC=2)=C3N=C1C1=CC=C(Br)C=C1 DYBJFUXHRFXNMX-UHFFFAOYSA-N 0.000 description 1
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 1
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- JSEQNGYLWKBMJI-UHFFFAOYSA-N 9,9-dimethyl-10h-acridine Chemical group C1=CC=C2C(C)(C)C3=CC=CC=C3NC2=C1 JSEQNGYLWKBMJI-UHFFFAOYSA-N 0.000 description 1
- HWTHOPMRUCFPBX-UHFFFAOYSA-N 9,9-diphenyl-10h-acridine Chemical compound C12=CC=CC=C2NC2=CC=CC=C2C1(C=1C=CC=CC=1)C1=CC=CC=C1 HWTHOPMRUCFPBX-UHFFFAOYSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 241001025261 Neoraja caerulea Species 0.000 description 1
- 229920000144 PEDOT:PSS Polymers 0.000 description 1
- IBTCZUXKFPQNMB-UHFFFAOYSA-N [B].OC=1C=CC=C2C=CC=NC12.OC=1C=CC=C2C=CC=NC12.OC=1C=CC=C2C=CC=NC12.OC=1C=CC=C2C=CC=NC12.[Li] Chemical group [B].OC=1C=CC=C2C=CC=NC12.OC=1C=CC=C2C=CC=NC12.OC=1C=CC=C2C=CC=NC12.OC=1C=CC=C2C=CC=NC12.[Li] IBTCZUXKFPQNMB-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000956 alloy Substances 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
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 230000005055 memory storage Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- ZTLUNQYQSIQSFK-UHFFFAOYSA-N n-[4-(4-aminophenyl)phenyl]naphthalen-1-amine Chemical compound C1=CC(N)=CC=C1C(C=C1)=CC=C1NC1=CC=CC2=CC=CC=C12 ZTLUNQYQSIQSFK-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- YNUJADNRNHJXDT-UHFFFAOYSA-N palladium;pentane-2,4-dione Chemical compound [Pd].CC(=O)CC(C)=O.CC(=O)CC(C)=O YNUJADNRNHJXDT-UHFFFAOYSA-N 0.000 description 1
- QJPQVXSHYBGQGM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 1
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 239000011970 polystyrene sulfonate Substances 0.000 description 1
- 229960002796 polystyrene sulfonate Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical group O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides a luminescent layer of an electroluminescent device, which is prepared by taking an acridine phenyl phenanthroimidazole compound as a raw material. The compound takes phenanthroimidazole as a matrix, introduces acridine phenyl and methoxyphenyl, improves the luminous performance of the compound as a thermal excitation delay luminescent material, and further improves the comprehensive performance of an organic electroluminescent device.
Description
Technical Field
The invention belongs to the technical field of electroluminescent materials, and particularly relates to an acridine phenyl phenanthroimidazole compound for preparing a luminescent layer of an electroluminescent device and a preparation method thereof.
Background
With the development of information technology, the demand and use requirements of semiconductor devices are increasing. However, the size miniaturization of the inorganic semiconductor memory that is currently mainstream is limited by a large number of materials and cost factors. The development of new memory storage structures and materials is facing new opportunities.
Organic light-emitting diodes (OLEDs) based on traditional fluorescent materials can only emit light by radiation using singlet excitons, the theoretical maximum Internal Quantum Efficiency (IQE) of which is only 25%; the second generation OLEDs of phosphorescent emissive materials based on noble metals, which have been developed later, accelerate the intersystem crossing process due to the heavy atom effect, so that the radiation of triplet excitons becomes possible, theoretically, the complete utilization of excitons can be achieved, and IQE can reach 100%. However, the phosphorescent emitting materials based on noble metals are expensive and triplet-triplet quenching occurs at high current, resulting in a large roll-off in device efficiency.
Organic molecules of thermally-excited delayed fluorescence (TADF) nature are generally donor-acceptor type molecules and have small triplet and singlet energies that are very poor. The small singlet state and triplet state energy range difference can convert triplet state electrons into singlet state electrons, thereby improving the utilization rate of electrons and realizing 100% internal quantum efficiency. However, at high concentrations, electron annihilation occurs, reducing efficiency.
Therefore, organic thermal excitation delayed fluorescence aromatic phosphine oxide materials are further researched, so that the electroluminescent device has good electron transmission capacity, current efficiency, power efficiency, external quantum efficiency and efficiency stability, the electroluminescent comprehensive performance is good, and the practical use requirements are met.
Disclosure of Invention
In order to solve the problems, the invention provides a luminescent layer of an electroluminescent device, which takes an acridine phenyl phenanthroimidazole compound as a raw material, introduces an acridine phenyl group on phenanthroimidazole to improve the thermal stability and the luminescent property of a molecule, is used as a thermal excitation delay fluorescent material, can be used for preparing the electroluminescent device, and has the advantages of low starting voltage, low energy consumption, high external quantum efficiency, good luminescent purity and effectively improved comprehensive performance, thereby completing the invention.
The invention aims to provide a luminescent layer of an electroluminescent device, which is prepared by taking one or more of acridine phenyl phenanthroimidazole compounds as raw materials,
it is also an object of the present invention to provide an acridinophenylphenanthoimidazole compound having the following structure:
wherein R is 1 、R 2 Each independently selected from hydrogen, phenyl or alkyl, preferably from hydrogen, phenyl or a carbon containing number C 1 -C 5 More preferably phenyl or methyl.
The invention also provides a preparation method of the acridine phenyl phenanthroimidazole compound, which comprises the step of preparing the acridine phenyl phenanthroimidazole compound by taking the acridine compound and the halogenated phenyl phenanthroimidazole as raw materials through catalytic coupling.
The method specifically comprises the following steps:
And 2, adding the 2- (4-halogenated-phenyl) -1- (4-methoxyphenyl) -1H phenanthro [9,10] imidazole and acridine compounds into a solvent II, and carrying out catalytic coupling reaction to obtain a reaction solution.
And 3, post-treating the reaction liquid to obtain the acridine phenyl phenanthroimidazole compound.
The invention also aims to provide the application of the acridine phenyl phenanthroimidazole compound as a luminescent layer material in preparing an electroluminescent device.
The acridine phenyl phenanthroimidazole compound for preparing the luminescent layer provided by the invention has the following beneficial effects:
(1) The invention takes phenanthroimidazole as a parent body, introduces acridine phenyl and methoxyphenyl, improves the hole electron transport property of the molecule, and improves the luminescent property to a certain degree.
(2) The acridine phenyl phenanthroimidazole compound is used as a luminescent layer material, has narrow electroluminescent peak position, is a deep blue light organic luminescent material with high luminescent color purity, and further improves the performance of the luminescent material.
(3) The electroluminescent device prepared by using the acridine phenyl phenanthroimidazole compound as a luminescent layer material has good comprehensive performance, effectively improves brightness, and has stable thermal performance and luminescent performance.
Drawings
FIG. 1 shows a UV spectrum and a fluorescence spectrum of compound I in example 1 of the present invention;
FIG. 2 shows a UV spectrum and a fluorescence spectrum of compound II in example 2 of the present invention;
FIG. 3 shows a thermogravimetric analysis of compound I in example 1 of the present invention;
FIG. 4 shows a thermogravimetric analysis of compound II in example 2 of the present invention;
FIG. 5 is a graph showing the voltage-luminance relationship of an electro-blue light device in example 1 of the present invention;
FIG. 6 shows the voltage-luminance relationship of an electro-blue light device in example 2 of the present invention;
FIG. 7 shows the luminance-current efficiency relationship of an electro-blue light device in example 1 of the present invention;
FIG. 8 is a graph showing the luminance-current efficiency relationship of an electro-blue light device in example 2 of the present invention;
FIG. 9 shows the luminance-power efficiency relationship of an electro-blue light device in example 1 of the present invention;
FIG. 10 is a graph showing the luminance-power efficiency relationship of an electro-blue light device in example 2 of the present invention;
FIG. 11 shows the luminance-external quantum efficiency curve efficiency of an electrogenerated blue light device in example 1 of the present invention;
FIG. 12 shows the luminance-external quantum efficiency curve efficiency of an electroblue device in example 2 of the present invention;
FIG. 13 is a graph showing an electroluminescence spectrum of a blue electroluminescent device in example 1 of the present invention;
FIG. 14 shows the electroluminescence spectrum of a blue electroluminescent device in example 2 of the present invention.
Detailed Description
The present invention will now be described in detail by way of specific embodiments, and features and advantages of the present invention will become more apparent and apparent from the following description.
The invention provides an acridine phenyl phenanthroimidazole compound for preparing a light-emitting layer of an electroluminescent device, which takes phenanthroimidazole as a matrix and introduces acridine phenyl and methoxyphenyl, aims to improve the hole electron transport property of a molecule so as to improve the thermal stability and the light-emitting brightness, is used as a light-emitting layer material to prepare the electroluminescent device, has high light-emitting purity, good thermal stability of the compound, stable performance of indexes such as external quantum efficiency, current efficiency, power efficiency and the like in the using process, has good device brightness, and can meet the use requirements of people.
The invention provides an acridine phenyl phenanthroimidazole compound, which has the following structure:
wherein R is 1 、R 2 Each independently selected from hydrogen, phenyl or alkyl, preferably from hydrogen, phenyl or a carbon containing number C 1 -C 5 More preferably phenyl or methyl.
Preferably, the acridine phenyl phenanthroimidazole compound is selected from the following compounds:
the acridine phenyl phenanthroimidazole compound can be used as a thermal excitation delayed fluorescence luminescent material, can be used as a luminescent layer material and is used for preparing an electroluminescent device.
The invention also provides a preparation method of the acridine phenyl phenanthroimidazole compound, which takes the acridine compound and the halogenated phenyl phenanthroimidazole as raw materials to prepare the acridine phenyl phenanthroimidazole compound through catalytic coupling.
The halophenyl phenanthroimidazole is 2- (4-halo-phenyl) -1- (4-methoxyphenyl) -1H phenanthro [9,10] imidazole, and is:
wherein, X is a halogenated group, preferably bromo, iodo or chloro, more preferably bromo.
The method specifically comprises the following steps:
The 2- (4-halogenated-phenyl) -1- (4-methoxyphenyl) -1H phenanthro [9,10] imidazole is prepared by condensation cyclization of phenanthrene-9, 10-diketone, 4-methoxyaniline and 4-halogenated-benzaldehyde under an acidic condition.
The 4-halo-benzaldehyde is selected from 4-bromobenzaldehyde, 4-chlorobenzaldehyde or 4-iodo-benzaldehyde, and is preferably 4-bromobenzaldehyde.
The solvent I is selected from one or more of organic acid, amide solvent, ketone solvent and sulfone solvent, preferably one or more of acetic acid, N-Dimethylformamide (DMF), N-Dimethylacetamide (DMA), dimethyl sulfoxide (DMSO), 1, 3-dimethyl-2-imidazolidinone (DMI) and cyclohexanone, and preferably acetic acid.
The molar volume ratio of the 9, 10-phenanthrene diketone to the solvent I is 13.5mmol (30-90) mL, preferably 13.5mmol (40-80) mL, and more preferably 13.5mmol (50-70) mL.
The condensation cyclization reaction is carried out in an acidic solution, and weakly acidic substances, such as ammonium acetate and acetic acid, are added into the reaction solution. The molar ratio of the ammonium acetate to the 9, 10-phenanthrene diketone is 13.5 (30-80), preferably 13.5 (40-70), and more preferably 13.5 (50-60).
The condensation cyclization reaction is carried out under the protective atmosphere, such as nitrogen and argon, and the heat preservation reaction is carried out for 12 to 45 hours, preferably 18 to 36 hours. The reaction temperature is 95 to 145 ℃, preferably 105 to 135 ℃, more preferably 115 to 125 ℃.
After the condensation cyclization reaction is finished, cooling to room temperature, filtering reaction liquid, washing and drying, and then carrying out column purification, wherein the eluent is preferably a mixed solvent of Dichloromethane (DCM) and Petroleum Ether (PE).
And 2, adding the 2- (4-halogenated-phenyl) -1- (4-methoxyphenyl) -1H phenanthro [9,10] imidazole and acridine compounds into a solvent II, and carrying out catalytic coupling reaction to obtain a reaction solution.
The acridine compound is selected from acridine or 9, 9-disubstituted acridine. In the 9, 9-disubstituted acridine, the substituent is selected from phenyl or alkyl, preferably from phenyl or a carbon-containing number C 1 -C 5 More preferably phenyl or methyl.
The molar ratio of the- (4-halogenated-phenyl) -1- (4-methoxyphenyl) -1H phenanthro [9,10] imidazole to the acridine compound is 1 (0.6-2.3), preferably 1 (0.8-1.8), and more preferably 1 (1.0-1.3).
The solvent II is selected from one or more of amide solvents, ketone solvents and aromatic solvents, preferably one or more of N, N-Dimethylformamide (DMF), N-Dimethylacetamide (DMA), toluene, xylene, 1, 3-dimethyl-2-imidazolidinone (DMI) and cyclohexanone, and more preferably xylene.
The molar volume ratio of the acridine compound to the solvent II is 2mmol (15-45) mL, preferably 2mmol (20-40) mL, and more preferably 2mmol (25-35) mL.
In the catalytic coupling reaction, the catalyst is selected from a divalent palladium compound, preferably a palladium salt or a palladium complex, preferably tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 ) One or more of palladium chloride, palladium acetate, bis (triphenylphosphine) palladium dichloride, bis (triphenylphosphine) palladium acetate and bis (acetylacetone) palladium, and more preferably palladium acetate or bis (tri-tert-butylphosphine) palladium.
The molar ratio of the acridine compound to the divalent palladium compound is (1.2-3.5): 0.1, preferably (1.5-3.0): 0.1, and more preferably (1.8-2.5): 0.1.
Preferably, a divalent palladium salt (such as palladium acetate) is used in the present invention in the presence of a reducing agent and tri-tert-butylphosphine.
The reducing agent is selected from potassium alkoxide or sodium alkoxide, preferably from potassium tert-butoxide or sodium tert-butoxide. In the invention, the reducing agent is alkaline and can also play a role of an acid binding agent.
The molar ratio of the acridine compound to the reducing agent is 2 (3.5-10.5), preferably 2 (4.5-9), and more preferably 2 (5.5-7.5).
The molar ratio of the divalent palladium salt to the tri-tert-butylphosphine is 1 (0.5-5.5), preferably 1 (1.5-4.5), and more preferably 1 (2.5-3.5).
The reaction is carried out for 10 to 18 hours, preferably 12 to 15 hours under a protective atmosphere. The reaction temperature is 115-150 deg.C, preferably 125-135 deg.C.
And 3, post-treating the reaction liquid to obtain the acridine phenyl phenanthroimidazole compound.
After the reaction was completed, it was cooled to room temperature, the precipitate was filtered off, and the filtrate was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to dryness. And purifying the obtained solid by chromatography, wherein the stationary phase is silica gel, the mobile phase eluent is a mixed solution of ethyl acetate and n-hexane, and the volume ratio of the two is 1: and 5, obtaining the acridine phenyl phenanthroimidazole compound.
The acridine phenyl phenanthroimidazole compound prepared by the method has high yield which can reach 80%. The compounds have deep blue electroluminescence, and both can be used as a light emitting layer of a non-doped electroluminescent device for an evaporation device, so that stable deep blue luminescence under high brightness is realized, and the compounds have high luminescent purity, high brightness and stable thermal performance and luminescent performance.
The invention provides application of the acridine phenyl phenanthroimidazole compound as a luminescent layer material in preparation of an electroluminescent device.
The electroluminescent device comprises a conductive anode layer, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and a cathode conductive layer.
The invention provides a preparation method of a luminescent device taking carbazole phenyl phenanthroimidazole aromatic phosphine oxide as a luminescent layer material, which specifically comprises the following steps:
1. preparing a conductive anode layer;
the conductive anode layer is prepared on a substrate layer. The conductive anode layer is selected from tin oxide conductive glass (ITO), transparent conductive polymers such as polyaniline, semi-transparent metals such as Au, preferably ITO or semi-transparent metals, more preferably ITO. Preferably, the conductive anode layer is evaporated by vacuum evaporation.
Preferably, the vacuum degree of vacuum deposition is 1X 10 -6 mbar, evaporation rate is set to be 0.1-0.3 nm/s, the evaporation material is indium tin oxide on the glass or plastic substrate, and the thickness of the anode conductive layer is 6-40 nm, preferably 8-30 nm, and more preferably 10-20 nm.
Preferably, the following hole injection layer, hole transport layer, light emitting layer, electron transport layer, electron injection layer and cathode conductive layer are prepared using a vacuum evaporation method.
2. Preparing a hole injection layer;
the hole injection layer is evaporated onto the anode conductive layer to a thickness of 4 to 35nm, preferably 6 to 25nm, more preferably 8 to 15nm, such as 10nm.
The hole injection layer material is selected from molybdenum oxide or poly 3, 4-ethylenedioxythiophene: polystyrene sulfonate (PEDOT: PSS), preferably molybdenum oxide, more preferably molybdenum oxide.
3. Preparing a hole transport layer;
the hole transport layer is evaporated onto the hole injection layer to a thickness of 15-65nm, preferably 25-55nm, more preferably 35-45nm, such as 40nm.
The hole transport layer material is selected from one or more of arylamine compounds and carbazole compounds, such as N, N ' -diphenyl-N, N ' - (1-naphthyl) -1,1' -biphenyl-4, 4' -diamine (NPB) and 9,9' - (1, 3-phenyl) di-9H-carbazole (mCP), and is preferably mCP.
4. Preparing a luminescent layer;
the light-emitting layer is further evaporated on the hole transport layer to a thickness of 35-75nm, preferably 40-65nm, more preferably 45-55nm, such as 50nm.
The light-emitting layer material comprises an aromatic phosphine oxide compound containing diphenylfluorene, preferably, also comprises bis [2- ((oxo) diphenylphosphino) phenyl ] ether (DPEPO), and the mass fraction of the DPEPO in the light-emitting layer material is 10-30%, preferably 15-25%, such as 20%.
5. Preparing an electron transport layer;
the electron transport layer material is selected from tris (8-hydroxyquinoline) aluminum (Alq 3), 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBi), 4, 7-diphenyl-1, 10-phenanthroline (Bphen), 3- (biphenyl-4-yl) -5- (4-tert-butylphenyl) -4-phenyl-4H-1, 2, 4-Triazole (TAZ) or bis [2- ((oxo) diphenylphosphino) phenyl ] ether (DPEPO), preferably DPEPO. The electron transport layer is evaporated onto the light emitting layer to a thickness of 25 to 55nm, more preferably 35 to 45nm, such as 40nm.
6. Preparing an electron injection layer;
the electron injection layer is evaporated on the electron transport layer to a thickness of 4 to 18nm, preferably 6 to 15nm, more preferably 8 to 12nm, such as 10nm.
The material of the electron injection layer is selected from lithium tetrakis (8-hydroxyquinoline) boron (LiBq) 4 ) Or LiF, preferably LiF.
7. And preparing a cathode conducting layer, and packaging to obtain the thermally-excited delayed fluorescence electroluminescent device.
The cathode conductive layer is evaporated on the electron injection layer to a thickness of 4-20nm, preferably 6-15nm, more preferably 8-12nm, such as 10nm.
The cathode conducting layer material is selected from a single metal cathode or an alloy cathode, such as metal Al.
The acridine phenyl phenanthroimidazole compound provided by the invention has good thermal stability and luminescence property, and can improve electron transport capability in a luminescence layer and optimize device performance when being used as the luminescence layer. The luminescent layer material is applied to the electroluminescent device, so that the high-efficiency blue-light thermally-excited delayed fluorescence device is obtained, the luminous efficiency of the device is greatly improved, and the stability of the luminous efficiency is good.
Examples
Example 1
(1) 4-bromobenzaldehyde (13.5 mmol) and phenanthrene-9, 10-dione (13.5 mmol) are mixed, and then a mixture of 4-bromobenzaldehyde (13.5 mmol) and phenanthrene-9, 10-dione (13.5 mmol), 4-methoxyaniline (67.5 mmol) and ammonium acetate (54.5 mmol) are added to acetic acid (60 mL) under an argon atmosphere, dissolved with stirring and reacted at 120 ℃ for 24 hours.
After the reaction, the reaction mixture was cooled to room temperature, and the reaction mixture was filtered, and the filter cake was washed with a mixed solution of acetic acid and water (volume ratio of both 1), dried in vacuo, and purified by chromatography to obtain 2- (4-bromophenyl) -1- (4-methoxyphenyl) -1H-phenanthro [9,10] imidazole (PhImBr, whose structural formula is specifically shown below), and the eluent was a mixed solvent of dichloromethane and petroleum ether (volume ratio of both 1.
(2) PhImBr (2 mmol), 9-dimethylacridine (2 mmol) and potassium tert-butoxide (6.9 mmol) were placed in a round-bottomed flask, xylene (30 mL) was added thereto, and they were mixed with stirring, and then nitrogen was introduced into the mixture for 1 hour. Under a nitrogen atmosphere, palladium (II) acetate (Pd (OAc) 2 (ii) a 0.1 mmol) and tri-tert-butylphosphine (P (tBu) 3 (ii) a 0.3 mmol) was added to the above reaction solution, and then the reaction was stirred at 130 ℃ overnight.
After the reaction was completed, it was cooled to room temperature, the precipitate was filtered off, and the filtrate was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to dryness. The resulting solid was purified by chromatography, silica gel (eluent: a mixed solvent of ethyl acetate and n-hexane in a volume ratio of 1: 5) to give 2- (4- (9, 9-dimethylacridin-10 (9H) -yl) phenyl) -1-4-methoxyphenyl) -1H-phenanthro [9,10] imidazole (PhImAc) as compound I.
The obtained compound I is subjected to mass spectrometry, and the flight time mass spectrum data thereof are as follows: m/z (%) 607.26 (100) [ M ] + ]。
The obtained compound I is tested by ultraviolet spectrum and fluorescence spectrum, and the test spectrogram is shown in figure 1.
The thermogravimetric analysis spectrum of the compound I is shown in FIG. 3, and the cracking temperature is 315 ℃.
(3) An electroluminescent blue-ray device is prepared by taking the obtained mixture of the compound I and bis [2- ((oxo) diphenylphosphino) phenyl ] ether (DPFPO) as a luminescent layer material, and the method is as follows:
1. putting the glass or plastic substrate cleaned by deionized water into a vacuum evaporation plating instrument for evaporation plating, wherein the vacuum degree is 1 multiplied by 10 -6 mbar, evaporation rate set at 0.1nm s -1 The evaporation material is Indium Tin Oxide (ITO) to obtain an anode conducting layer with the thickness of 10 nm;
2. evaporating a hole injection layer material MoOx on the anode conducting layer to obtain a hole injection layer with the thickness of 10 nm;
3. evaporating a hole transport layer material 9,9' - (1, 3-phenyl) di-9H-carbazole (mCP) on the hole injection layer to obtain a hole transport layer with the thickness of 40 nm;
4. and (3) evaporating a luminescent layer material on the hole transport layer: the material of the luminescent layer is a mixture of a compound I and DPFPO, wherein the mass fraction of the DPFPO is 20 percent, and the luminescent layer with the thickness of 50nm is obtained;
5. continuously evaporating DPFPO on the luminescent layer to obtain an electron transport layer with the thickness of 40 nm;
6. evaporating and plating an electron injection layer material LiF on the electron transport layer, wherein the thickness of the electron injection layer is 10 nm;
7. and evaporating a cathode conducting layer which is made of aluminum and has the thickness of 10nm on the electron injection layer to obtain the electro-blue light device 1.
The structure of the electric blue light device 1 in the embodiment is as follows: ITO/MoOx (10 nm)/mcp (40 nm)/(I) DPFPO (20%) 50 nm/(I) (40 nm)/LiF (10 nm)/Al.
Example 2
(1) Compound II (2- (4- (9, 9-diphenylacridin-10 (9H) -yl) phenyl) -1- (4-methoxyphenyl) -1H-phenanthro [9,10-d ] imidazole) was prepared according to the method in example 1, with the exception that: the 9, 9-dimethylacridine was replaced with an equimolar amount of 9, 9-diphenylacridine.
And carrying out mass spectrum test on the obtained compound II, wherein the flight time mass spectrum data of the compound II are as follows: m/z (%) < 731.29 (100) [ M ] + ]；
And testing the obtained compound II by ultraviolet spectrum and fluorescence spectrum, wherein the test spectrogram is shown in figure 2.
The thermogravimetric analysis spectrum of the compound II is shown in FIG. 4, and the cracking temperature is 454 ℃ as shown in the graph.
(2) According to the preparation method of the blue electroluminescent device in example 1, a mixture of the compound ii and DPFPO (wherein, the mass fraction of DPFPO is 20%) is used as a luminescent layer material to prepare a blue electroluminescent device 2. The structure is as follows: ITO/MoOx (10 nm)/mcp (40 nm)/(II) DPFPO (20%) 50 nm/(II) (40 nm)/LiF (10 nm)/Al.
Examples of the experiments
Experimental example 1
Fig. 5 and 6 show voltage-luminance relationship curves of the blue electroluminescent device 1-2 prepared in test example 1-2, and it can be seen that the blue electroluminescent device 1-2 prepared in example 1-2 has a turn-on voltage of 4.1V and a turn-on voltage of 3.3V, respectively.
Experimental example 2
As shown in fig. 7 and 8, the luminance-current efficiency relationship curves of the electro-blue light device 1-2 prepared in test example 1-2 show:
the electroluminescent blue light device 1 has a luminance of 532cd m -2 When the current efficiency reaches the maximum value of 3.65 cd.A -1 。
The blue electroluminescent device 2 has a brightness of 642cd m -2 When the current efficiency reaches the maximum value of 2.30 cd.A -1 。
Experimental example 3
As shown in fig. 9 and 10, the luminance-power efficiency relationship curves of the blue electroluminescent device 1-2 prepared in test example 1-2 were confirmed,
the electroluminescent blue light device 1 has a luminance of 532cd m -2 When the power efficiency reaches the maximum value of 2.01 lm.W -1 。
The electroluminescent blue light device 2 has a luminance of cd m -2 When the power efficiency reaches the maximum value of 1.32 lm.W -1 。
Experimental example 4
As shown in fig. 11 and 12, the luminance-external quantum efficiency relationship curves of the blue electroluminescent devices prepared in test examples 1-2 were confirmed,
the electroluminescent blue light device 1 has a luminance of 532cd m -22 Then, the maximum external quantum efficiency of 3.68% was obtained.
The blue electroluminescent device 2 has a brightness of 642cd m -2 Then, the maximum external quantum efficiency of 2.50% is obtained.
Experimental example 5
The electroluminescence spectra of the electroluminescent blue device 1-2 prepared in test example 1-2 are shown in fig. 13 and 14, respectively.
From the above data, the electroluminescence peaks of the electro-blue device prepared in example 1-2 were at 431 and 414nm, respectively.
The invention has been described in detail with reference to specific embodiments and/or illustrative examples and the accompanying drawings, which, however, should not be construed as limiting the invention. Those skilled in the art will appreciate that various equivalent substitutions, modifications or improvements may be made to the embodiments and implementations of the invention without departing from the spirit and scope of the invention, and are within the scope of the invention. The scope of the invention is defined by the appended claims.
Claims (10)
1. A luminescent layer of an electroluminescent device is characterized in that the luminescent layer is prepared by taking one or more of acridine phenyl phenanthroimidazole compounds as raw materials,
the acridine phenyl phenanthroimidazole compound is selected from compounds having the following structures:
wherein R is 1 、R 2 Each independently selected from hydrogen, phenyl or alkyl, preferably from hydrogen, phenyl or a carbon containing number C 1 -C 5 More preferably phenyl or methyl;
preferably, the raw material of the light emitting layer further includes bis [2- ((oxo) diphenylphosphino) phenyl ] ether (DPEPO).
2. An acridinophenylphenanthoimidazole compound characterized by the following structure:
wherein R is 1 、R 2 Each independently selected from hydrogen, phenyl or alkyl, preferably from hydrogen, phenyl or a carbon containing number C 1 -C 5 More preferably phenyl or methyl.
3. The compound according to claim 2, wherein said acridinophenylphenanthoimidazole compound is selected from the group consisting of:
4. a preparation method of an acridine phenyl phenanthroimidazole compound is characterized by taking an acridine compound and halogenated phenyl phenanthroimidazole as raw materials, and carrying out catalytic coupling to prepare the acridine phenyl phenanthroimidazole compound.
5. The method according to claim 4, wherein the halophenylphenanthroimidazole is 2- (4-halo-phenyl) -1- (4-methoxyphenyl) -1H phenanthro [9,10] imidazole, which is:
wherein, X is a halogenated group, preferably bromo, iodo or chloro, more preferably bromo.
6. The method according to claim 4, characterized in that it comprises in particular the steps of:
step 1, phenanthrene-9, 10-diketone, 4-methoxyaniline and 4-halogenated-benzaldehyde are added into a solvent I and subjected to condensation cyclization reaction to obtain 2- (4-halogenated-phenyl) -1- (4-methoxyphenyl) -1H phenanthro [9,10] imidazole;
step 2, adding 2- (4-halogenated-phenyl) -1- (4-methoxyphenyl) -1H phenanthro [9,10] imidazole and acridine compounds into a solvent II, and carrying out catalytic coupling reaction to obtain a reaction solution;
and 3, post-treating the reaction liquid to obtain the acridine phenyl phenanthroimidazole compound.
7. The method according to claim 6, wherein in step 1, the 2- (4-halo-phenyl) -1- (4-methoxyphenyl) -1H phenanthro [9,10] imidazole is prepared by condensation ring formation of phenanthrene-9, 10-dione, 4-methoxyaniline and 4-halo-benzaldehyde under acidic conditions;
the 4-halo-benzaldehyde is selected from 4-bromobenzaldehyde, 4-chlorobenzaldehyde or 4-iodo-benzaldehyde, and is preferably 4-bromobenzaldehyde;
the condensation cyclization reaction is carried out in an acidic solution, and weakly acidic substances, such as ammonium acetate and acetic acid, are added into the reaction solution.
8. The method according to claim 4, wherein in step 2, the acridine compound is selected from acridine or 9, 9-disubstituted acridine, wherein in the 9, 9-disubstituted acridine, the substituent is selected from phenyl or alkyl, preferably selected from phenyl or carbon number C 1 -C 5 More preferably phenyl or methyl;
the molar ratio of the- (4-halogenated-phenyl) -1- (4-methoxyphenyl) -1H phenanthro [9,10] imidazole to the acridine compound is 1 (0.6-2.3), preferably 1 (0.8-1.8), and more preferably 1 (1.0-1.3).
9. The method according to claim 3, wherein in step 2, the solvent II is selected from one or more of amide solvents, ketone solvents and aromatic solvents, preferably from one or more of N, N-Dimethylformamide (DMF), N-Dimethylacetamide (DMA), toluene, xylene, 1, 3-dimethyl-2-imidazolidinone (DMI) and cyclohexanone, and more preferably from xylene;
the molar volume ratio of the acridine compound to the solvent II is 2mmol (15-45) mL, preferably 2mmol (20-40) mL, and more preferably 2mmol (25-35) mL.
10. An application of acridine phenyl phenanthroimidazole compound as luminescent layer material in preparing electroluminescent device.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210939882.2A CN115724825A (en) | 2022-08-05 | 2022-08-05 | Acridine phenyl phenanthroimidazole compound for preparing luminescent layer of electroluminescent device and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210939882.2A CN115724825A (en) | 2022-08-05 | 2022-08-05 | Acridine phenyl phenanthroimidazole compound for preparing luminescent layer of electroluminescent device and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN115724825A true CN115724825A (en) | 2023-03-03 |
Family
ID=85292691
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210939882.2A Pending CN115724825A (en) | 2022-08-05 | 2022-08-05 | Acridine phenyl phenanthroimidazole compound for preparing luminescent layer of electroluminescent device and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115724825A (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108530357A (en) * | 2017-03-03 | 2018-09-14 | 中国科学院宁波材料技术与工程研究所 | Acridine D-A type thermal activation delayed fluorescence material, preparation method and application |
| CN110305107A (en) * | 2018-03-27 | 2019-10-08 | 武汉尚赛光电科技有限公司 | Thermotropic delayed fluorescence material with phenanthro- glyoxaline structure and its preparation method and application |
| CN111333615A (en) * | 2018-12-19 | 2020-06-26 | 三星显示有限公司 | Heterocyclic compound and organic light-emitting device including the same |
| CN113563314A (en) * | 2021-07-13 | 2021-10-29 | 广东工业大学 | Phenanthroimidazole derivative and preparation method and application thereof |
| CN114773317A (en) * | 2022-05-18 | 2022-07-22 | 山东科技大学 | Donor-acceptor type organic blue light material, preparation method and application thereof, and electroluminescent device |
-
2022
- 2022-08-05 CN CN202210939882.2A patent/CN115724825A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108530357A (en) * | 2017-03-03 | 2018-09-14 | 中国科学院宁波材料技术与工程研究所 | Acridine D-A type thermal activation delayed fluorescence material, preparation method and application |
| CN110305107A (en) * | 2018-03-27 | 2019-10-08 | 武汉尚赛光电科技有限公司 | Thermotropic delayed fluorescence material with phenanthro- glyoxaline structure and its preparation method and application |
| CN111333615A (en) * | 2018-12-19 | 2020-06-26 | 三星显示有限公司 | Heterocyclic compound and organic light-emitting device including the same |
| CN113563314A (en) * | 2021-07-13 | 2021-10-29 | 广东工业大学 | Phenanthroimidazole derivative and preparation method and application thereof |
| CN114773317A (en) * | 2022-05-18 | 2022-07-22 | 山东科技大学 | Donor-acceptor type organic blue light material, preparation method and application thereof, and electroluminescent device |
Non-Patent Citations (3)
| Title |
|---|
| DONG YUEL KWON: "Theoretical Study of Imidazole Derivatives for Blue Thermally Activated Delayed Fluorescence Emitter", J. NANOSCI. NANOTECHNOL, vol. 16, no. 10, pages 11014 * |
| SHENGBING XIAO: "Efficient and stable deep-blue narrow-spectrum electroluminescence based on hybridized local and charge-transfer (HLCT) state", DYES AND PIGMENTS, vol. 193, pages 109482 * |
| ZHI HUANG: "Highly twisted bipolar emitter for efficient nondoped deep-blue electroluminescence", DYES AND PIGMENTS, vol. 140, pages 328 - 336, XP029921062, DOI: 10.1016/j.dyepig.2017.01.028 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6869402B2 (en) | Nitrogen-containing compounds, organic electroluminescence devices and photoelectric conversion devices | |
| CN110862381B (en) | Organic electroluminescent compound and preparation method and application thereof | |
| EP1902013B1 (en) | Novel anthracene derivatives, process for preparation thereof, and organic electronic light emitting device using the same | |
| JP5638612B2 (en) | Novel heterocyclic derivative and organic light emitting device using the same | |
| JP7251711B2 (en) | organic light emitting device | |
| TW201038576A (en) | Materials for organic electroluminescent devices | |
| He et al. | Asymmetrically twisted anthracene derivatives as highly efficient deep-blue emitters for organic light-emitting diodes | |
| KR101132462B1 (en) | New anthracene derivatives and organic electronic device using the same | |
| TW200812936A (en) | Anthracene derivatives, organic electronic devices using anthracene derivatives, and electronic apparatuses comprising organic electronic device | |
| WO2021082714A1 (en) | Nitrogen-containing compound, electronic component and electronic device | |
| KR20210002670A (en) | Organic electroluminescent materials and devices | |
| CN112979687A (en) | Thermal activation delayed fluorescent material and preparation method and application thereof | |
| JPWO2007026846A1 (en) | Arylamine compound and organic electroluminescence device | |
| KR102657637B1 (en) | Anthracene compound, coating composition and organic light emitting device comprising same | |
| CN113121584A (en) | Heterocyclic compound and organic electroluminescent device comprising same | |
| WO2023241569A1 (en) | Aza-adamantane compound and organic electroluminescent element | |
| KR102615340B1 (en) | Organic electroluminescent material, method for producing the same, and organic electroluminescent device | |
| TWI387575B (en) | Synthesis of triphenylene and pyrene based aromatics and their application in oleds | |
| JP2007246468A (en) | Fluorene compound and organic electroluminescent element using the same | |
| KR20200011911A (en) | Multicyclic compound and organic light emitting device comprising the same | |
| KR101434726B1 (en) | Anthracene derivative and organic electroluminescence device using the same | |
| KR102657636B1 (en) | Anthracene compound, coating composition and organic light emitting device comprising same | |
| CN115724825A (en) | Acridine phenyl phenanthroimidazole compound for preparing luminescent layer of electroluminescent device and preparation method thereof | |
| CN110305112B (en) | Organic photoelectric material and application thereof | |
| KR20210062496A (en) | Compound for organic optoelectronic and organic optoelectronic device including the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |