CN107068880A - A kind of organic electroluminescence device containing diaryl ketone compounds and its application - Google Patents
A kind of organic electroluminescence device containing diaryl ketone compounds and its application Download PDFInfo
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- CN107068880A CN107068880A CN201610261347.0A CN201610261347A CN107068880A CN 107068880 A CN107068880 A CN 107068880A CN 201610261347 A CN201610261347 A CN 201610261347A CN 107068880 A CN107068880 A CN 107068880A
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- -1 diaryl ketone compounds Chemical class 0.000 title claims abstract description 21
- 238000005401 electroluminescence Methods 0.000 title abstract description 3
- 239000000463 material Substances 0.000 claims abstract description 168
- 150000001875 compounds Chemical class 0.000 claims abstract description 70
- 239000002019 doping agent Substances 0.000 claims abstract description 5
- 238000002347 injection Methods 0.000 claims description 65
- 239000007924 injection Substances 0.000 claims description 65
- 230000005525 hole transport Effects 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000002947 alkylene group Chemical group 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 claims description 10
- 229910052711 selenium Inorganic materials 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical group [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 claims description 5
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical class [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 4
- 229910003002 lithium salt Inorganic materials 0.000 claims description 4
- 159000000002 lithium salts Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 3
- GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical compound [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 claims description 3
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims description 3
- 229910052808 lithium carbonate Inorganic materials 0.000 claims description 3
- 229920001621 AMOLED Polymers 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- AYTVLULEEPNWAX-UHFFFAOYSA-N cesium;azide Chemical compound [Cs+].[N-]=[N+]=[N-] AYTVLULEEPNWAX-UHFFFAOYSA-N 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical group [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002560 nitrile group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000005259 triarylamine group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 230000005855 radiation Effects 0.000 abstract description 3
- 230000005540 biological transmission Effects 0.000 abstract 2
- 125000000468 ketone group Chemical group 0.000 abstract 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 abstract 1
- 230000027756 respiratory electron transport chain Effects 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 276
- 230000000903 blocking effect Effects 0.000 description 36
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 238000010586 diagram Methods 0.000 description 19
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 18
- 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 18
- 238000012360 testing method Methods 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 238000005070 sampling Methods 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 0 *c1c(*)c(*)c(c(*)c(c(*)c(*)c(*)c2*)c2c2*)c2c1* Chemical compound *c1c(*)c(*)c(c(*)c(c(*)c(*)c(*)c2*)c2c2*)c2c1* 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000005284 excitation Effects 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- JGGSOWGJMBNDHS-UHFFFAOYSA-N 10-phenyl-5h-phenazine Chemical compound C12=CC=CC=C2NC2=CC=CC=C2N1C1=CC=CC=C1 JGGSOWGJMBNDHS-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 239000008204 material by function Substances 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 2
- IJRKLHTZAIFUTB-UHFFFAOYSA-N 5-nitro-2-(2-phenylethylamino)benzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1NCCC1=CC=CC=C1 IJRKLHTZAIFUTB-UHFFFAOYSA-N 0.000 description 2
- BGGALFIXXQOTPY-NRFANRHFSA-N C1(=C(C2=C(C=C1)N(C(C#N)=C2)C[C@@H](N1CCN(CC1)S(=O)(=O)C)C)C)CN1CCC(CC1)NC1=NC(=NC2=C1C=C(S2)CC(F)(F)F)NC Chemical compound C1(=C(C2=C(C=C1)N(C(C#N)=C2)C[C@@H](N1CCN(CC1)S(=O)(=O)C)C)C)CN1CCC(CC1)NC1=NC(=NC2=C1C=C(S2)CC(F)(F)F)NC BGGALFIXXQOTPY-NRFANRHFSA-N 0.000 description 2
- 229940126657 Compound 17 Drugs 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- JCVYQVHAGOZGIX-UHFFFAOYSA-N bis(2-bromophenyl)methanone Chemical compound BrC1=CC=CC=C1C(=O)C1=CC=CC=C1Br JCVYQVHAGOZGIX-UHFFFAOYSA-N 0.000 description 2
- LFABNOYDEODDFX-UHFFFAOYSA-N bis(4-bromophenyl)methanone Chemical compound C1=CC(Br)=CC=C1C(=O)C1=CC=C(Br)C=C1 LFABNOYDEODDFX-UHFFFAOYSA-N 0.000 description 2
- 229940126142 compound 16 Drugs 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 238000003475 lamination Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- ZMYKITJYWFYRFJ-UHFFFAOYSA-N 4-oxo-4-(2-phenylethylamino)butanoic acid Chemical compound OC(=O)CCC(=O)NCCC1=CC=CC=C1 ZMYKITJYWFYRFJ-UHFFFAOYSA-N 0.000 description 1
- RFWRTEVGLOAXSY-ZETCQYMHSA-N CC[B-2](C1)=[I-]C[C@H]1C=C Chemical compound CC[B-2](C1)=[I-]C[C@H]1C=C RFWRTEVGLOAXSY-ZETCQYMHSA-N 0.000 description 1
- 101100181929 Caenorhabditis elegans lin-3 gene Proteins 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
- FBJQQHKHSYAVEA-UHFFFAOYSA-N bis(4-bromonaphthalen-1-yl)methanone Chemical compound BrC1=CC=C(C2=CC=CC=C12)C(=O)C1=CC=C(C2=CC=CC=C12)Br FBJQQHKHSYAVEA-UHFFFAOYSA-N 0.000 description 1
- NTOCRCSAFQXOOG-UHFFFAOYSA-N bis(5-bromothiophen-2-yl)methanone Chemical compound S1C(Br)=CC=C1C(=O)C1=CC=C(Br)S1 NTOCRCSAFQXOOG-UHFFFAOYSA-N 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 101150051397 csn3 gene Proteins 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000011982 device technology Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000001748 luminescence spectrum Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000004776 molecular orbital Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 1
- 229960000303 topotecan Drugs 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/301—Details of OLEDs
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention discloses a kind of organic electroluminescence device containing diaryl ketone compounds and its application, the device includes hole transmission layer, luminescent layer, electron transfer layer, the device emitting layer material includes the compound containing diaryl ketone, shown in the structural formula of compound such as formula (1).Diaryl ketone group material of the present invention is because with less triplet state and singlet energy difference, therefore it is easily achieved energy transmission between Subjective and Objective material, the energy scattered and disappeared in the form of heat originally is set to be easily obtained utilization, lift luminescent layer radiation transistion efficiency, so as to be easier to the high efficiency for obtaining device, further, when dopant material selection is fluorescent material, it is easier to obtain the luminous radiation of dopant material, so as to be easier to obtain the long-life of material.
Description
Technical Field
The invention relates to the technical field of semiconductors, in particular to an organic electroluminescent device with a luminescent layer made of diaryl ketone compounds and application thereof.
Background
The Organic Light Emission Diodes (OLED) device technology can be used for manufacturing novel display products and novel lighting products, is expected to replace the existing liquid crystal display and fluorescent lamp lighting, and has wide application prospect.
The OLED light-emitting device is of a sandwich structure and comprises electrode material film layers and organic functional materials clamped between different electrode film layers, and the various different functional materials are mutually overlapped together according to the application to form the OLED light-emitting device. When voltage is applied to two end electrodes of the OLED light-emitting device as a current device, positive and negative charges in the organic layer functional material film layer are acted through an electric field, and the positive and negative charges are further compounded in the light-emitting layer, namely OLED electroluminescence is generated.
However, conventional organic fluorescent materials can only emit light using 25% singlet excitons formed by electrical excitation, the internal quantum efficiency of the device is low (up to 25%), the external quantum efficiency is generally lower than 5%, and there is a great difference from the efficiency of phosphorescent devices, although phosphorescent materials can effectively emit light using singlet excitons and triplet excitons formed by electrical excitation due to strong spin-orbit coupling of heavy atom centers, and the internal quantum efficiency of the device reaches 100%ST) The triplet excitons may be converted to singlet excitons by intersystem crossing to emit light. This can make full use of singlet excitons and triplet excitons formed under electrical excitation, and the internal quantum efficiency of the device can reach 100%. Meanwhile, the material has controllable structure, stable property, low price and no need of precious metal, and has wide application prospect in the field of OLED.
Although TADF materials can theoretically achieve 100% exciton utilization, there are actually the following problems:
(1) the T1 and S1 states of the designed molecule have strong CT characteristics, a very small energy gap of S1-T1 states, although high T can be achieved by the TADF process1→S1State exciton conversion but at the same time results in a low S1 state radiative transition rate, and therefore it is difficult to achieve both (or both) high exciton utilization and high fluorescence radiation efficiency;
(2) even though doped devices have been employed to mitigate the T exciton concentration quenching effect, most devices of TADF materials suffer from severe roll-off in efficiency at high current densities.
In terms of the actual demand of the current OLED display illumination industry, the development of the current OLED material is far from enough, and lags behind the requirements of panel manufacturing enterprises, and the development of organic functional materials with higher performance is very important as a material enterprise.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides an organic electroluminescent device containing diaryl ketone compounds and application thereof. The diaryl ketone compound based on the TADF mechanism is applied to an organic light-emitting diode as a light-emitting layer material, has good photoelectric property, and can meet the requirements of OLED device enterprises, particularly OLED display panels and OLED lighting enterprises.
The technical scheme of the invention is as follows:
an organic electroluminescent device containing diaryl ketone compounds comprises a hole transport layer, a luminescent layer and an electron transport layer, wherein the luminescent layer material of the device comprises diaryl ketone compounds, and the structural formula of the compounds is shown as a general formula (1):
in the general formula (1), Ar represents C6-30Aryl, furyl, thienyl, pyrrolyl, quinolyl or carbazolyl;
in the general formula (1), R is represented by a general formula (2):
wherein, X1Is oxygen atom, sulfur atom, selenium atom, C1-10One of a linear or branched alkyl substituted alkylene, aryl substituted alkylene, alkyl or aryl substituted amine group;
R1、R2independently select hydrogen or a structure shown in a general formula (3):
wherein a isX2、X3Respectively represent oxygen atom, sulfur atom, selenium atom, C1-10One of a linear or branched alkyl substituted alkylene, aryl substituted alkylene, alkyl or aryl substituted amine group; a and CL1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL4-CL5Key, CL‘1-CL’2Key, CL‘2-CL’3Key, CL‘3-CL’4Bond or CL‘4-CL’5And (4) key connection.
In the compounds when a representsAnd with CL4-CL5Bond or CL‘4-CL’5When connected to a bond, X1And X2Overlap in position of (2), taking only X1Or X2；X3Represented by oxygen atom, sulfur atom, selenium atom, C1-10One of a linear or branched alkyl substituted alkylene, an aryl substituted alkylene, an alkyl or an aryl substituted amine.
In the compound R1、R2Are each hydrogen, X1Is selenium atom, C1-10One of a linear or branched alkyl substituted alkylene, an aryl substituted alkylene, an alkyl or an aryl substituted amine.
In the compound R1、R2At least one being other than hydrogen, X1Is oxygen atom, sulfur atom, selenium atom, C1-10One of a linear or branched alkyl substituted alkylene, an aryl substituted alkylene, an alkyl or an aryl substituted amine.
The compound is represented by general formula (4) or general formula (5):
the specific structural formula of the compound is as follows:
any one of the above.
When the compound represented by the general formula (1) is used as a host material of the light-emitting layer, one of materials represented by the following general formula (6), (7), (8) or (9) is used as a doping material of the light-emitting layer:
in the general formula (6), B1-B10 are each independently hydrogen or C1-30Alkyl or alkoxy substituted by straight-chain or branched alkyl, substituted or unsubstituted C6-30Aryl, substituted or unsubstituted 3-to 30-membered heteroaryl; B1-B10 are not hydrogen at the same time;
in the general formula (7), Y1-Y6 are respectively and independently one of oxygen, carbon and nitrogen atoms; represented as a ring formed by a linkage of two atom-containing groups via any chemical bond;
Y1-Y4 in the general formulas (8) and (9) are respectively and independently one of oxygen, carbon and nitrogen atoms;it is expressed that a group containing two atoms is linked to form a ring by an arbitrary chemical bond.
The hole transport layer is made of a compound containing triarylamine groups, and the structure of the hole transport layer is shown as a general formula (10):
in the general formula (10), D1 to D3 each independently represents a substituted or unsubstituted C6-30Aryl, substituted or unsubstituted 3-to 30-membered heteroaryl; D1-D3 may be the same or different.
The material of the electron transport layer is one of the materials shown in the following general formula (11), (12), (13), (14) or (15):
E1-E10 in the general formula (11), the general formula (12), the general formula (13), the general formula (14) and the general formula (15) are respectively and independently hydrogen and C1-30Alkyl or alkoxy substituted by straight-chain or branched alkyl, substituted or unsubstituted C6-30Aryl, substituted or unsubstituted 3-to 30-membered heteroaryl; E1-E10 are not hydrogen at the same time.
The organic electroluminescent device also comprises a hole injection layer; the material of the hole injection layer is one of the materials shown in the following structural general formula (16), (17) or (18):
in the general formula (16), F1 to F3 each independently represents a substituted or unsubstituted C6-30Aryl, substituted or unsubstituted 3-to 30-membered heteroaryl; F1-F3 may be the same or different;
in the general formulas (17) and (18), G1-G6 each independently represents hydrogen, a nitrile group, halogen, an amide group, an alkoxy group, an ester group, a nitro group, or C1-30Straight or branched alkyl substituted carbon atom, substituted or unsubstituted C6-30Aryl, 3-to 30-membered heteroaryl; G1-G6 are not hydrogen at the same time.
The organic electroluminescent device also comprises an electron injection layer; the material of the electron injection layer is one of lithium, lithium salt or cesium salt; the lithium salt is 8-hydroxyquinoline lithium, lithium fluoride, lithium carbonate or lithium azide; the cesium salt is cesium fluoride, cesium carbonate or cesium azide.
The mass ratio of the doping material of the light-emitting layer to the main material of the light-emitting layer is 0.005-0.2: 1.
The compound represented by the general formula (1) can also be used as a doping material of a light-emitting layer.
An application of the organic electroluminescent device is used for preparing a top-emitting OLED (organic light emitting diode) light emitting device.
An application of the organic electroluminescent device is applied to an AM-OLED display.
The beneficial technical effects of the invention are as follows:
the diaryl ketone compound composing the OLED luminescent device has the structural characteristics of TADF, can easily realize very small energy gap difference of S1-T1 states, can easily realize the intersystem crossing from a triplet state to a singlet state under the excitation condition, can not emit light originally, can convert heat dissipated in the form of heat into energy capable of generating light energy, and is expected to obtain extremely high efficiency.
Based on the above principle analysis, the OLED light-emitting device of the present invention may select a fluorescent material as a doping material, may select a phosphorescent material as a doping material, and may also directly use the TADF material of the present invention as a doping material.
When the diaryl ketone compound is used as a main material of an OLED (organic light emitting diode) luminescent device and matched with iridium, platinum phosphorescent materials or anthracene fluorescent materials, the current efficiency, the power efficiency and the external quantum efficiency of the device are greatly improved; meanwhile, the service life of the device is obviously prolonged. Furthermore, after a hole and electron injection layer is introduced on the structure of the OLED device layer, the contact interface of the transparent anode, the metal cathode and the organic material is more stable, and the hole and electron injection effect is improved; the hole transport layer can be laminated into two or more layers, the hole transport layer adjacent to one side of the light-emitting layer can be named as an Electron Blocking Layer (EBL) to provide an electron blocking effect, so that the exciton recombination efficiency in the light-emitting layer is improved, and the hole transport layer adjacent to one side of the hole injection layer plays a role in hole transport and exciton transfer barrier reduction; the electron transport layer can be laminated into two or more layers, the electron transport layer adjacent to one side of the luminescent layer can be named as a Hole Blocking Layer (HBL) to provide a hole blocking effect, so that the exciton recombination efficiency in the luminescent layer is improved, and the electron transport layer adjacent to one side of the electron injection layer plays roles in electron transport and exciton transfer barrier reduction. However, it should be noted that each of these layers need not be present.
The combined effect of the OLED device compounds of the present invention: the driving voltage of the device is reduced, the current efficiency, the power efficiency and the external quantum efficiency are further improved, and the service life of the device is obviously prolonged. The organic light emitting diode has good application effect in OLED light emitting devices and good industrialization prospect.
Surprisingly, it has been found that the combination of compounds described in more detail below achieves this object and leads to improvements in the organic electroluminescent devices, in particular in terms of voltage, efficiency and lifetime. This is particularly true for red or green phosphorescent electroluminescent devices, especially when the device structures and material combinations of the present invention are used.
Drawings
FIG. 1 is a schematic structural diagram of a stacked OLED device according to an embodiment of the present invention;
in fig. 1:1 is a transparent substrate, 2 is an ITO anode layer, 3 is a Hole Injection Layer (HIL), 4 is a Hole Transport Layer (HTL), 5 is an Electron Blocking Layer (EBL), 6 is an emission layer (EML), 7 is a Hole Blocking Layer (HBL), 8 is an Electron Transport Layer (ETL), 9 is an Electron Injection Layer (EIL), and 10 is a cathode reflective electrode layer.
FIG. 2 is a structural diagram of key raw materials used in an embodiment of the device of the present invention.
Detailed Description
The present invention will be described in detail with reference to the accompanying drawings and examples.
EXAMPLE 1 Compound 1
Specific synthetic routes for this compound are now provided:
a250 ml four-necked flask was charged with 0.01mol of 4,4' -dibromobenzophenone and 0.025mol of 6, 6-dimethyl-6, 11-dihydro-13-oxa-11-aza-indole [1,2-b ] in an atmosphere of nitrogen gas]Anthracene, 0.03mol of sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3，1×10-4Heating and refluxing tri-tert-butylphosphine and 150ml toluene for 24 hr, sampling the sample, and reacting completely; natural coolingFiltering, rotatably steaming the filtrate, and passing through a silica gel column to obtain the target product with the purity of 99.2 percent and the yield of 67.00 percent.
Elemental analysis Structure (molecular formula C)55H40N2O3): theoretical value C, 85.03; h, 5.19; n, 3.61; o, 6.18; test values are: c, 84.99; h, 5.21; n, 3.70; and O, 6.10.
HPLC-MS: the molecular weight of the material is 776.30, and the measured molecular weight is 776.83.
EXAMPLE 2 Compound 6
Specific synthetic routes for this compound are now provided:
in a 250ml four-necked flask, under a nitrogen-purged atmosphere, 0.01mol of 4,4' -dibromobenzophenone and 0.025mol of 11, 11-dimethyl-4 a,6,11,13 a-tetrahydro-13-thia-6-aza-indole [1,2-b ] were added]Anthracene, 0.03mol of sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3，1×10-4Heating and refluxing tri-tert-butylphosphine and 150ml toluene for 24 hr, sampling the sample, and reacting completely; naturally cooling, filtering, rotatably evaporating filtrate, and passing through a silica gel column to obtain a target product with the purity of 99.0 percent and the yield of 69.00 percent.
Elemental analysis Structure (molecular formula C)55H42N2OS2): theoretical value C, 81.45; h, 5.22; n, 3.45; o, 1.97; test values are: c, 81.50; h, 5.21; n, 3.40; and O, 2.01.
HPLC-MS: the molecular weight of the material is 810.27, and the measured molecular weight is 810.65.
EXAMPLE 3 Compound 11
Specific synthetic routes for this compound are now provided:
a250 ml four-necked flask was charged with 0.01mol of 2,2' -dibromobenzophenone, and 0.025mol of 6, 6-dimethyl-13-phenyl-11, 13-dihydro-6H-11, 13-diaza-indole [1,2-b ] under a nitrogen-purged atmosphere]Anthracene, 0.03mol of sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3，1×10-4Heating and refluxing tri-tert-butylphosphine and 150ml toluene for 24 hr, sampling the sample, and reacting completely; naturally cooling, filtering, rotatably evaporating filtrate, and passing through a silica gel column to obtain a target product with the purity of 99.5 percent and the yield of 72.00 percent.
Elemental analysis Structure (molecular formula C)66H49N4O): theoretical value C, 86.80; h, 5.44; n, 6.04; o, 1.73; test values are: c, 86.63; h, 5.29; n, 6.30; o, 1.78.
HPLC-MS: the molecular weight of the material is 926.40, and the measured molecular weight is 926.52.
EXAMPLE 4 Compound 16
Specific synthetic routes for this compound are now provided:
a250 ml four-necked flask was charged with 0.01mol of 2,2' -dibromobenzophenone and 0.025mol of 11,11,13, 13-tetramethyl-11, 13-dihydro-6H-6-aza-indole [1,2-b ] in an atmosphere of nitrogen gas]Anthracene, 0.03mol of sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3，1×10-4mol tri-tert-butylphosphine, 150ml toluene, heated to reflux for 24 hours, sampling the spot plate, and the reaction was complete. Naturally cooling, filtering, rotatably evaporating filtrate, and passing through a silica gel column to obtain a target product with the purity of 99.2 percent and the yield of 66.00 percent.
Elemental analysis Structure (molecular formula C)61H54NO): theoretical value C, 88.16; h, 6.55; n, 3.37; o, 1.93; test values are: c, 88.20; h, 6.62; n, 3.32; o, 1.86.
HPLC-MS: the molecular weight of the material is 830.42, and the measured molecular weight is 830.62.
EXAMPLE 5 Synthesis of Compound 17
Specific synthetic routes for this compound are now provided:
a250 ml four-necked flask was charged with 0.01mol of bis (4-bromo-naphthalen-1-yl) -methanone, 0.025mol of 6, 6-dimethyl-6, 11-dihydro-13-oxa-11-aza-indole [1,2-b ] under a nitrogen atmosphere]Anthracene, 0.03mol of sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3，1×10-4mol tri-tert-butylphosphine, 150ml toluene, heated to reflux for 24 hours, sampling the spot plate, and the reaction was complete. Naturally cooling, filtering, rotatably evaporating filtrate, and passing through a silica gel column to obtain a target product with the purity of 99.2 percent and the yield of 66.80 percent.
Elemental analysis Structure (molecular formula C)63H44N2O3): theoretical value C, 86.28; h, 5.06; n, 3.19; o, 5.47; test values are: c, 86.20; h, 5.12; n, 3.12; and O, 5.56.
HPLC-MS: the molecular weight of the material is 876.34, and the measured molecular weight is 876.62.
EXAMPLE 6 Synthesis of Compound 140
Specific synthetic routes for this compound are now provided:
in a 250ml four-necked flask, 0.01mol of bis (4-bromoanthracen-1-yl) -methanone, 0.025mol of 5-phenyl-5, 10-dihydro-phenazine, 0.03mol of sodium tert-butoxide, 1 × 10 mol under a nitrogen atmosphere-4mol Pd2(dba)3，1×10-4mol tri-tert-butylphosphine, 150ml toluene, heated to reflux for 24 hours, sampling the spot plate, and the reaction was complete. Naturally cooling, filtering, rotatably steaming the filtrate, and passing through a silica gel column to obtain the target product with the purity of 99.8 percent and the yield of 82.00 percent.
Elemental analysis Structure (molecular formula C)65H42N4O): theoretical value C, 87.22; h, 4.73; n, 6.26; o, 1.79; test values are: c, 87.20; h, 4.72; n, 6.32; o, 1.76.
HPLC-MS: the molecular weight of the material is 894.34, and the measured molecular weight is 894.38.
EXAMPLE 7 Synthesis of Compound 143
Specific synthetic routes for this compound are now provided:
in a 250ml four-necked flask, 0.01mol of bis- (5-bromo-thiophen-2-yl) -methanone, 0.025mol of 5-phenyl-5, 10-dihydro-phenazine, 0.03mol of sodium tert-butoxide, 1 × 10, 10 mol under an atmosphere of nitrogen gas-4mol Pd2(dba)3，1×10-4mol tri-tert-butylphosphine, 150ml toluene, heated to reflux for 24 hours, sampling the spot plate, and the reaction was complete. Naturally cooling, filtering, rotatably evaporating filtrate, and passing through a silica gel column to obtain the target product with the purity of 99.9 percent and the yield of 86.00 percent.
Elemental analysis Structure (molecular formula C)45H30N4OS2): theoretical value C, 76.46; h, 4.28; n, 7.93; o, 2.26; s, 9.07; test values are: c, 76.40; h, 4.32; n, 7.92; o, 2.32; and S,9.04。
HPLC-MS: the molecular weight of the material is 706.19, and the measured molecular weight is 706.38.
EXAMPLE 8 Synthesis of Compound 144
Specific synthetic routes for this compound are now provided:
in a 250ml four-necked flask, 0.01mol of bis (5-bromo-1-phenyl-1H-pyrrol-2-yl) -methanone, 0.025mol of 5-phenyl-5, 10-dihydro-phenazine, 0.03mol of sodium tert-butoxide, 1 × 10 mol-4mol Pd2(dba)3，1×10-4mol tri-tert-butylphosphine, 150ml toluene, heated to reflux for 24 hours, sampling the spot plate, and the reaction was complete. Naturally cooling, filtering, rotatably evaporating filtrate, and passing through a silica gel column to obtain the target product with the purity of 99.9 percent and the yield of 86.00 percent.
Elemental analysis Structure (molecular formula C)57H40N6O): theoretical value C, 82.99; h, 4.89; n, 10.19; o, 1.94; test values are: c, 82.90; h, 4.92; n, 10.32; o, 1.86.
HPLC-MS: the molecular weight of the material is 824.33, and the measured molecular weight is 824.57.
EXAMPLE 9 Synthesis of Compound 145
Specific synthetic routes for this compound are now provided:
a250 ml four-necked flask was charged with 0.01mol of bis (8-bromo-quinolin-5-yl) -methanone, 0.025mol of 5-phenyl under a nitrogen atmosphere5, 10-dihydro-phenazine, 0.03mol of sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3，1×10-4mol tri-tert-butylphosphine, 150ml toluene, heated to reflux for 24 hours, sampling the spot plate, and the reaction was complete. Naturally cooling, filtering, rotatably evaporating filtrate, and passing through a silica gel column to obtain a target product with the purity of 99.9 percent and the yield of 84.00 percent.
Elemental analysis Structure (molecular formula C)55H36N6O): theoretical value C, 82.89; h, 4.55; n, 10.55; o, 2.01; test values are: c, 82.93; h, 4.50; n, 10.59; o, 1.98.
HPLC-MS: the molecular weight of the material is 796.30, and the measured molecular weight is 796.68.
EXAMPLE 10 Synthesis of Compound 147
Specific synthetic routes for this compound are now provided:
compound 147 was prepared as in example 1 except that the starting material 14, 14-dimethyl-5, 14-dihydro-7, 12-dioxa-5-aza-pentacene was substituted for 6, 6-dimethyl-6, 11-dihydro-13-oxa-11-aza-indole [1,2-b ] anthracene.
EXAMPLE 11 Synthesis of Compound 151
Specific synthetic routes for this compound are now provided:
compound 151 was prepared as in example 1, except that the starting material, 14H-5-oxa-14-aza-pentacene, was substituted for 6, 6-dimethyl-6, 11-dihydro-13-oxa-11-aza-indole [1,2-b ] anthracene.
EXAMPLE 12 Synthesis of Compound 159
Specific synthetic routes for this compound are now provided:
compound 159 was prepared as in example 1, except that the starting material 14, 14-dimethyl-5-phenyl-7, 14-dihydro-5H-12-oxa-5, 7-diaza-pentacene was used in place of 6, 6-dimethyl-6, 11-dihydro-13-oxa-11-aza-indole [1,2-b ] anthracene.
EXAMPLE 13 Synthesis of Compound 160
Compound 160 was prepared as in example 1, except that starting material a was substituted for 6, 6-dimethyl-6, 11-dihydro-13-oxa-11-aza-indole [1,2-b ] anthracene.
EXAMPLE 14 Synthesis of Compound 161
Compound 161 was prepared as in example 1, except that starting material B was substituted for 6, 6-dimethyl-6, 11-dihydro-13-oxa-11-aza-indole [1,2-B ] anthracene.
EXAMPLE 15 Synthesis of Compound 163
Compound 163 was prepared as in example 3, except that starting material C was substituted for 6, 6-dimethyl-13-phenyl-11, 13-dihydro-6H-11, 13-diaza-indole [1,2-b ] anthracene.
EXAMPLE 16 Synthesis of Compound 164
Compound 164 was prepared as in example 1, except that starting material D was substituted for 6, 6-dimethyl-6, 11-dihydro-13-oxa-11-aza-indole [1,2-b ] anthracene.
EXAMPLE 17 Synthesis of Compound 166
Compound 166 was prepared as in example 1, except that starting material E was substituted for 6, 6-dimethyl-6, 11-dihydro-13-oxa-11-aza-indole [1,2-b ] anthracene.
The compound of the invention can be used as a luminescent layer material, and the thermal performance, the luminescence spectrum and the HOMO and LUMO energy levels of the compound 1, the compound 164 and the existing material CBP are measured, and the test results are shown in Table 1.
TABLE 1
Note: thermal weight lossThe temperature Td was a temperature at which 1% weight loss was observed in a nitrogen atmosphere, and was measured on a TGA-50H thermogravimetric analyzer of Shimadzu corporation, Japan, and the nitrogen flow rate was 20 mL/min; lambda [ alpha ]PLThe fluorescence emission wavelength of the sample solution is measured by using a Japanese topotecan SR-3 spectroradiometer; phi f is the fluorescence quantum efficiency of the solid powder (measured by using a solid fluorescence quantum efficiency testing system consisting of a Maya2000Pro fiber optic spectrometer of American marine optics, a C-701 integrating sphere of American blue-phenanthrene company and a LLS-LED light source of marine optics, in a method of Adv. Mater.1997, 9, 230-; the highest occupied molecular orbital HOMO energy level and the lowest occupied molecular orbital LUMO energy level were measured by a photoelectron emission spectrometer (AC-2 type PESA) and an ultraviolet-visible spectrophotometer, and the test was conducted in an atmospheric environment.
As can be seen from the data in the table above, the compound of the present invention has suitable HOMO and LUMO energy levels and high thermal stability, and is suitable as a host material of a light emitting layer; meanwhile, the compound has a proper light-emitting spectrum and a high phi f, so that the efficiency and the service life of an OLED device using the compound as a doping material are improved.
The effect of the compound combinations of the present invention in the use of the devices is explained in detail below by device examples 1-16 and device comparative example 1. Compared with the device embodiment 1, the device embodiments 2 to 16 and the device comparative example 1 of the present invention have the same manufacturing process, and adopt the same substrate material and electrode material, except that the device has different lamination structure, matching material and film thickness. The device stack structure is shown in table 2. The device test data is shown in table 3.
Device example 1
The device stack structure is shown in a device structure schematic diagram 1: comprises a hole transport layer 4, a light emitting layer 6, and an electron transport layer 8.
ITO anode layer 2 (thickness: 150 nm)/hole transport layer 4 (thickness: 120nm, material: HT 6)/light-emitting layer 6 (thickness: 40nm, material: compound 1 and GD1 mixed at a weight ratio of 90: 10)/electron transport layer 8 (thickness: 35nm, materials: ET2 and EI1, mass ratio 1:1)/Al (thickness: 100 nm).
The preparation process comprises the following steps:
the ITO anode layer 2 (film thickness 150nm) was washed, and then washed with alkali, washed with pure water, and dried, followed by ultraviolet-ozone washing to remove organic residues on the surface of the transparent ITO.
Evaporating a hole transport layer on the washed ITO anode layer 2 by using a vacuum evaporation device, wherein the hole transport layer is made of HT6, the thickness of the film is 120nm, and the layer is used as a hole transport layer 4 in a device structure;
and depositing a light-emitting layer on the hole transport layer 4 by a vacuum deposition method, wherein the material of the light-emitting layer uses a compound 1 as a host material and GD1 as a doping material, and the doping mass ratio is 9: 1, the thickness of a luminescent layer is 40nm, and the luminescent layer is used as a luminescent layer 6 in a device structure;
evaporating an electron transport layer on the light-emitting layer 6 in a vacuum evaporation mode, wherein the material of the electron transport layer is formed by mixing and doping ET2 and EI1, the doping amount ratio is 1:1, the film thickness is 35nm, and the layer is used as an electron transport layer 8 in a device structure;
on the electron transport layer 8, a cathode aluminum layer was deposited by vacuum deposition to a film thickness of 100nm, and this layer was used as the cathode reflective electrode layer 10.
After the OLED light emitting device was fabricated as described above, the anode and cathode were connected by a known driving circuit, and the light emitting efficiency, the light emission spectrum, and the current-voltage characteristics of the device were measured.
Device example 2
The device stack structure is shown in a device structure schematic diagram 1: comprising a hole injection layer 3, a hole transport layer 4, a light-emitting layer 6 and an electron transport layer 8.
ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 10nm, material: HI 1)/hole transport layer 4 (thickness: 110nm, material: HT 2)/light-emitting layer 6 (thickness: 40nm, material: compound 11 and GD2 intermingled in weight ratio 88: 12)/electron transport layer 8 (thickness: 35nm, material: ET02 and EI1, mass ratio 1:1)/Al (thickness: 100 nm).
Device example 3
The device stack structure is shown in a device structure schematic diagram 1: comprising a hole injection layer 3, a hole transport layer 4, a light emitting layer 6, an electron transport layer 8 and an electron injection layer 9.
ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 10nm, material: HI 2)/hole transport layer 4 (thickness: 110nm, material: HT 4)/luminescent layer 6 (thickness: 40nm, material: compound 16 and GD2 mixed in a weight ratio of 88: 12)/electron transport layer 8 (thickness: 35nm, material: ET3 and EI1, mass ratio of 1: 1)/electron injection layer 9 (thickness: 1nm, material: LiN3)/Al (thickness: 100 nm).
Device example 4
The device stack structure is shown in a device structure schematic diagram 1: including a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, and an electron transport layer 8.
ITO anode layer (thickness: 150 nm)/hole injection layer 3 (thickness: 10nm, material: HI 1)/hole transport layer 4 (thickness: 90nm, material: HT 3)/electron blocking layer 5 (thickness: 20nm, material: EB 2)/luminescent layer 6 (thickness: 40nm, material: compound 17 and GD3 intermingled at a weight ratio of 89: 11)/electron transport layer 8 (thickness: 35nm, material: ET3 and EI1, mass ratio of 1:1)/Al (thickness: 100 nm).
Device example 5
The device stack structure is shown in a device structure schematic diagram 1: including a hole injection layer 3, a hole transport layer 4, a light emitting layer 6, an electron transport layer 8, and an electron injection layer 9.
ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 50nm, materials: HI3 and HT3, co-doped at a mass ratio of 5: 95)/hole transport layer 4 (thickness: 70nm, material: HT 3)/light-emitting layer 6 (thickness: 40nm, material: compound 143 and GD3 co-doped at a weight ratio of 89: 11)/electron transport layer 8 (thickness: 35nm, material: ET 3)/electron injection layer 9 (thickness: 1nm, material: Li)/Al (thickness: 100 nm).
Device example 6
The device stack structure is shown in a device structure schematic diagram 1: including a hole injection layer 3, a hole transport layer 4, a light emitting layer 6, an electron transport layer 8, and an electron injection layer 9.
ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 50nm, materials: HI4 and HT3, mixed at a mass ratio of 5: 95)/hole transport layer 4 (thickness: 70nm, material: HT 6)/light-emitting layer 6 (thickness: 40nm, material: compound 144 and GD4 mixed at a weight ratio of 92: 8)/electron transport layer 8 (thickness: 35nm, materials: ET4 and EI1, mass ratio of 1: 1)/electron injection layer 9 (thickness: 1nm, material: LiF)/Al (thickness: 100 nm).
Device example 7
The device stack structure is shown in a device structure schematic diagram 1: comprising a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7 and an electron transport layer 8.
ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 10nm, material: HI 1)/hole transport layer 4 (thickness: 90nm, material: HT 6)/electron blocking layer 5 (thickness: 20nm, material: EB 1)/light-emitting layer 6 (thickness: 40nm, material: compound 145 and GD4 intermingled at a weight ratio of 92: 8)/hole blocking layer 7 (thickness: 20nm, material: HB 1)/electron transport layer 8 (thickness: 15nm, material: ET2 and EI1, mass ratio 1:1)/Al (thickness: 100 nm).
Device example 8
The device stack structure is shown in a device structure schematic diagram 1: comprising a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, an electron transport layer 8 and an electron transport layer 9.
ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 50nm, materials: HI5 and HT3, mixed at a mass ratio of 5: 95)/hole transport layer 4 (thickness: 50nm, material: HT 5)/electron blocking layer 5 (thickness: 20nm, material: EB 3)/light-emitting layer 6 (thickness: 40nm, mixed at a weight ratio of 92: 8 of material: compound 147 and GD 5)/electron transport layer 8 (thickness: 35nm, materials: ET2 and EI1, mass ratio of 1: 1)/electron injection layer 9 (thickness: 1nm, material: Cs2CO3)/Al (thickness: 100nm)
Device example 9
The device stack structure is shown in a device structure schematic diagram 1: comprising a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, an electron transport layer 8 and an electron injection layer 9.
ITO anode layer (thickness: 150 nm)/hole injection layer 3 (thickness: 50nm, materials: HI6 and HT4, mixed at a mass ratio of 5: 95)/hole transport layer 4 (thickness: 50nm, material: HT 6)/electron blocking layer 5 (thickness: 20nm, material: EB 2)/light-emitting layer 6 (thickness: 40nm, mixed at a weight ratio of 95: 5 of material: compound 159 and GD 6)/electron transport layer 8 (thickness: 35nm, materials: ET2 and EI1, mass ratio of 1: 1)/electron injection layer 9 (thickness: 1nm, material: EI1)/Al (thickness: 100 nm).
Device example 10
The device stack structure is shown in a device structure schematic diagram 1: comprising a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, an electron transport layer 8 and an electron injection layer 9.
ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 10nm, material: HI 1)/hole transport layer 4 (thickness: 90nm, material: HT 3)/electron blocking layer 5 (thickness: 20nm, material: EB 1)/light-emitting layer 6 (thickness: 40nm, material: compound 160 and GD5 intermingled at a weight ratio of 92: 8)/hole blocking layer 7 (thickness: 25nm, material: HB 1)/electron transport layer 8 (thickness: 10nm, material: ET 5)/electron injection layer 9 (thickness: 1nm, material: EI1)/Al (thickness: 100 nm).
Device example 11
The device stack structure is shown in a device structure schematic diagram 1: comprising a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, an electron transport layer 8 and an electron injection layer 9.
ITO anode layer 2 (thickness: 150 nm)/hole injection layer (thickness: 50nm, materials: HI5 and HT6, mixed at a mass ratio of 5: 95)/hole transport layer 4 (thickness: 50nm, material: HT 6)/electron blocking layer 5 (thickness: 20nm, material: EB 2)/luminescent layer 6 (thickness: 40nm, mixed at a weight ratio of 92: 8 of material: compound 161 and GD 4)/hole blocking layer 7 (thickness: 15nm, material: HB 1)/electron transport layer 8 (thickness: 20nm, materials: ET2 and EI1, mass ratio of 1: 1)/electron injection layer 9 (thickness: 1nm, material: Li2CO3)/Al (thickness: 100 nm).
Device example 12
The device stack structure is shown in a device structure schematic diagram 1: including a hole injection layer 3, a hole transport layer 4, a light emitting layer 6, a hole blocking layer 7, an electron transport layer 8, and an electron injection layer 9.
ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 50nm, materials: HI5 and HT3, co-doped at a mass ratio of 5: 95)/hole transport layer 4 (thickness: 70nm, material: HT 6)/light-emitting layer 6 (thickness: 40nm, material: compound 163 and GD6 co-doped at a weight ratio of 95: 5)/hole blocking layer 7 (thickness: 15nm, material: HB 1)/electron transport layer 8 (thickness: 20nm, material: ET 6)/electron injection layer 9 (thickness: 1nm, material: CsF)/Al (thickness: 100 nm).
Device example 13
The device stack structure is shown in a device structure schematic diagram 1: comprising a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, an electron transport layer 8 and an electron injection layer 9.
ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 50nm, materials: HI5 and HT3, mixed in a mass ratio of 5: 95)/hole transport layer 4 (thickness: 50nm, material: HT 6)/electron blocking layer 5 (thickness: 20nm, material: EB 2)/light-emitting layer 6 (thickness: 40nm, mixed in a weight ratio of 88: 12 of material: compound 164 and GD 2)/electron transport layer 8 (thickness: 35nm, materials: ET2 and EI1, mass ratio of 1: 1)/electron injection layer 9 (thickness: 1nm, material: CsN3)/Al (thickness: 100 nm).
Device example 14
The device stack structure is shown in a device structure schematic diagram 1: comprising a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7 and an electron transport layer 8.
ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 50nm, materials: HI5 and HT3, mixed in mass ratio 5: 95)/hole transport layer 4 (thickness: 50nm, material: HT 6)/electron blocking layer 5 (thickness: 20nm, material: EB 2)/light emitting layer 6 (thickness: 40nm, mixed in weight ratio 60: 30: 10 of materials: compound 166, GH2 and GD 2)/hole blocking layer 7 (thickness 15nm, material: EB 2)/electron transport layer 8 (thickness: 20nm, materials: ET2 and EI1, mass ratio 1:1)/Al (thickness: 100 nm).
Device example 15
The device stack structure is shown in a device structure schematic diagram 1: comprising a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7 and an electron transport layer 8.
ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 50nm, materials: HI5 and HT3, mixed in mass ratio 5: 95)/hole transport layer 4 (thickness: 50nm, material: HT 6)/electron blocking layer 5 (thickness: 20nm, material: EB 2)/light emitting layer 6 (thickness: 40nm, mixed in weight ratio 60: 30: 10 of material: compound 161, GH4 and GD 2)/hole blocking layer 7 (thickness 15nm, material: HB 1)/electron transport layer 8 (thickness: 20nm, materials: ET2 and EI1, mass ratio 1:1)/Al (thickness: 100 nm).
Device example 16
The device stack structure is shown in a device structure schematic diagram 1: including a hole injection layer 3, a hole transport layer 4, a light emitting layer 6, an electron transport layer 8, and an electron injection layer 9.
ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 50nm, materials: HI4 and HT3, co-doped at a mass ratio of 5: 95)/hole transport layer 4 (thickness: 70nm, material: HT 6)/light emitting layer 6 (thickness: 40nm, material: GH3 and compound 164 co-doped at a weight ratio of 92: 8)/electron transport layer 8 (thickness: 35nm, materials: ET4 and EI1, mass ratio of 1: 1)/electron injection layer 9 (thickness: 1nm, material: LiF)/Al (thickness: 100 nm).
Device comparative example 1
The device stack structure is shown in a device structure schematic diagram 1: including a hole transport layer 4, a light emitting layer 6, an electron transport layer 8, and an electron injection layer 9.
ITO anode layer 2 (thickness: 150 nm)/hole transport layer 4 (thickness: 120nm, material: HTI)/light-emitting layer 6 (thickness: 40nm, material: GH1 and GD1 mixed at a weight ratio of 90: 10)/electron transport layer 8 (thickness: 35nm, material: ET 1)/electron injection layer 9 (thickness: 1nm, material: LiF)/Al (thickness: 100 nm).
The OLEDs were characterized by standard methods, calculated from current/voltage/luminous density characteristic lines exhibiting lambertian emission characteristics, and lifetime measured. Determined at 1000cd/m2Electroluminescence spectra at luminance, CIEx and y color coordinates were calculated, and device test data are shown in table 3.
TABLE 2
TABLE 3
Note: the device test performance was defined as comparative example 1, and each performance index of the device of comparative example 1 was 1.0. The current efficiency of comparative example 1 was 32.6cd/A (@1000 cd/m)2) (ii) a The driving voltage was 5.6v (@1000cd/m 2); CIE color coordinates (0.34, 0.63); LT95 lifetime decay was 3.5Hr at 5000 brightness.
Table 3 summarizes the OLED devices at 1000cd/m2Required voltage for brightness, achieved current efficiency, and at 5000cd/m2LT95 decays lifetime at brightness.
Device embodiment 1 compared with device comparative example 1, after the luminescent layer material of the present invention was replaced and the materials of the present invention were combined into a stacked device, the voltage of the device was reduced, the current efficiency was improved by 60%, and the lifetime was improved by 1 time; the device embodiments 2-16 are designed according to the invention, and the material collocation and the device lamination combination further improve the device data; as shown in device examples 14 and 15, when the diaryl ketone material of the invention is used as a mixed host material, very good performance data are further obtained; as shown in device example 16, the diaryl ketone material of the present invention also provides excellent performance data when used as a dopant material for an emissive layer.
Therefore, the above description is only for the purpose of illustrating the preferred embodiments of the present invention and should not be taken as limiting the invention, and any modifications, equivalents, improvements and the like that are within the spirit and principle of the present invention should be included in the scope of the present invention.
Claims (15)
1. An organic electroluminescent device containing diaryl ketone compounds comprises a hole transport layer, a luminescent layer and an electron transport layer, and is characterized in that the luminescent layer material of the device comprises diaryl ketone-containing compounds, and the structural formula of the compounds is shown as a general formula (1):
in the general formula (1), Ar represents C6-30Aryl, furanA group selected from the group consisting of phenyl, thienyl, pyrrolyl, quinolinyl and carbazolyl;
in the general formula (1), R is represented by a general formula (2):
wherein,
X1is oxygen atom, sulfur atom, selenium atom, C1-10One of a linear or branched alkyl substituted alkylene, aryl substituted alkylene, alkyl or aryl substituted amine group;
R1、R2independently select hydrogen or a structure shown in a general formula (3):
wherein a isX2、X3Respectively represent oxygen atom, sulfur atom, selenium atom, C1-10One of a linear or branched alkyl substituted alkylene, aryl substituted alkylene, alkyl or aryl substituted amine group; a and CL1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL4-CL5Key, CL‘1-CL’2Key, CL‘2-CL’3Key, CL‘3-CL’4Bond or CL‘4-CL’5And (4) key connection.
2. The organic electroluminescent device according to claim 1, wherein when a representsAnd with CL4-CL5Bond or CL‘4-CL’5When connected to a bond, X1And X2Overlap in position of (2), taking only X1Or X2；X3Represented by oxygen atom, sulfur atom, selenium atom, C1-10One of a linear or branched alkyl substituted alkylene, aryl substituted alkylene, alkyl or aryl substituted amine group; a through CL4-CL5Bond or CL‘4-CL’5The bond is connected to the middle benzene ring of the general formula (2).
3. The organic electroluminescent device according to claim 1, wherein R in the compound is1、R2Are each hydrogen, X1Is selenium atom, C1-10One of a linear or branched alkyl substituted alkylene, an aryl substituted alkylene, an alkyl or an aryl substituted amine.
4. The organic electroluminescent device according to claim 1, wherein R in the compound is1、R2At least one being other than hydrogen, X1Is oxygen atom, sulfur atom, selenium atom, C1-10One of a linear or branched alkyl substituted alkylene, an aryl substituted alkylene, an alkyl or an aryl substituted amine.
5. The compound according to claim 1, characterized in that the compound is represented by general formula (4) or general formula (5):
6. the organic electroluminescent device according to claim 1, wherein the compound has a specific structural formula:
any one of the above.
7. The organic electroluminescent element according to claim 1, wherein the compound represented by the general formula (1) is used as a host material of the light-emitting layer, and the dopant material of the light-emitting layer is one of materials represented by the following general formulae (6), (7), (8) or (9):
in the general formula (6), B1-B10 are each independently hydrogen or C1-30Alkyl or alkoxy substituted by straight-chain or branched alkyl, substituted or unsubstituted C6-30Aryl, substituted or unsubstituted 3-to 30-membered heteroaryl; B1-B10 are not hydrogen at the same time;
in the general formula (7), Y1-Y6 are respectively and independently one of oxygen, carbon and nitrogen atoms; respectively represent that groups containing two atoms are connected through any chemical bond to form a ring;
Y1-Y4 in the general formulas (8) and (9) are respectively and independently one of oxygen, carbon and nitrogen atoms;respectively, are represented as groups containing two atoms connected to form a ring by an arbitrary chemical bond.
8. The organic electroluminescent device according to claim 1, wherein the hole transport layer is made of a compound containing triarylamine group, and has a structure represented by general formula (10):
in the general formula (10), D1 to D3 each independently represents a substituted or unsubstituted C6-30Aryl, substituted or unsubstituted 3-to 30-membered heteroaryl; D1-D3 may be the same or different.
9. The organic electroluminescent device according to claim 1, wherein the material of the electron transport layer is one of materials represented by the following general formula (11), (12), (13), (14) or (15):
E1-E10 in the general formula (11), the general formula (12), the general formula (13), the general formula (14) and the general formula (15) are respectively and independently hydrogen and C1-30Alkyl or alkoxy substituted by straight-chain or branched alkyl, substituted or unsubstituted C6-30Aryl, substituted or unsubstituted 3-to 30-membered heteroaryl; E1-E10 are not hydrogen at the same time.
10. The organic electroluminescent device according to claim 1, wherein the light-emitting device further comprises a hole injection layer; the material of the hole injection layer is one of the materials shown in the following structural general formula (16), (17) or (18):
in the general formula (16), F1 to F3 each independently represents a substituted or unsubstituted C6-30Aryl, substituted or unsubstituted 3-to 30-membered heteroaryl; F1-F3 may be the same or different;
in the general formulas (17) and (18), G1-G6 each independently represents hydrogen, a nitrile group, halogen, an amide group, an alkoxy group, an ester group, a nitro group, or C1-30Straight or branched alkyl substituted carbon atom, substituted or unsubstituted C6-30Aryl, 3-to 30-membered heteroaryl; G1-G6 are not hydrogen at the same time.
11. The organic electroluminescent device according to claim 1, wherein the light-emitting device further comprises an electron injection layer; the material of the electron injection layer is one of lithium, lithium salt or cesium salt; the lithium salt is 8-hydroxyquinoline lithium, lithium fluoride, lithium carbonate or lithium azide; the cesium salt is cesium fluoride, cesium carbonate or cesium azide.
12. The organic electroluminescent device according to claim 1, wherein the mass ratio of the dopant material of the light-emitting layer to the host material of the light-emitting layer is 0.005-0.2: 1.
13. The organic electroluminescent device according to claim 1, wherein the compound represented by the general formula (1) is further used as a doping material for a light-emitting layer.
14. Use of an organic electroluminescent device according to any one of claims 1 to 13 for the manufacture of a top-emitting OLED light-emitting device.
15. Use of an organic electroluminescent device as claimed in any one of claims 1 to 13, characterized in that the organic electroluminescent device is used in AM-OLED displays.
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| WO2019200875A1 (en) * | 2018-04-16 | 2019-10-24 | 华南理工大学 | Organic electroluminescent material containing carbonyl group, and application thereof to oled |
| CN110416418A (en) * | 2018-04-28 | 2019-11-05 | 江苏三月光电科技有限公司 | Organic electroluminescence device and display including it |
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| CN110957427A (en) * | 2018-09-27 | 2020-04-03 | 江苏三月光电科技有限公司 | Organic electroluminescent device |
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| CN108659010A (en) * | 2017-03-27 | 2018-10-16 | 北京绿人科技有限责任公司 | A kind of organic compound and its application in organic electroluminescence device |
| WO2019200875A1 (en) * | 2018-04-16 | 2019-10-24 | 华南理工大学 | Organic electroluminescent material containing carbonyl group, and application thereof to oled |
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| CN110416418A (en) * | 2018-04-28 | 2019-11-05 | 江苏三月光电科技有限公司 | Organic electroluminescence device and display including it |
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| CN110957424A (en) * | 2018-09-27 | 2020-04-03 | 江苏三月光电科技有限公司 | Multispectral OLED device and preparation method thereof |
| CN110957427A (en) * | 2018-09-27 | 2020-04-03 | 江苏三月光电科技有限公司 | Organic electroluminescent device |
| CN110957425A (en) * | 2018-09-27 | 2020-04-03 | 江苏三月光电科技有限公司 | High-performance OLED light-emitting device |
| US11053437B2 (en) | 2019-06-28 | 2021-07-06 | Idemitsu Kosan Co., Ltd. | Compound, material for organic electroluminescent devices, organic electroluminescent device and electronic device |
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