CN109694378A - 多杂芳族化合物及使用其的有机电激发光元件 - Google Patents
多杂芳族化合物及使用其的有机电激发光元件 Download PDFInfo
- Publication number
- CN109694378A CN109694378A CN201810870135.1A CN201810870135A CN109694378A CN 109694378 A CN109694378 A CN 109694378A CN 201810870135 A CN201810870135 A CN 201810870135A CN 109694378 A CN109694378 A CN 109694378A
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- Prior art keywords
- heteroaromatics
- unsubstituted
- substituted
- electroluminescent element
- organic electroluminescent
- 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.)
- Granted
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- 150000002390 heteroarenes Chemical class 0.000 title claims abstract description 44
- 239000000463 material Substances 0.000 claims abstract description 56
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 150000001721 carbon Chemical group 0.000 claims description 19
- 239000002019 doping agent Substances 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 150000004982 aromatic amines Chemical class 0.000 claims description 10
- 230000003111 delayed effect Effects 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 238000007725 thermal activation Methods 0.000 claims description 8
- 239000010409 thin film Substances 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 229910052711 selenium Inorganic materials 0.000 claims description 4
- -1 compound Compound Chemical class 0.000 claims description 2
- 239000010408 film Substances 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 abstract description 24
- 239000010410 layer Substances 0.000 description 68
- 150000001875 compounds Chemical class 0.000 description 25
- 230000015572 biosynthetic process Effects 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 15
- 239000000203 mixture Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 230000008569 process Effects 0.000 description 9
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 230000005525 hole transport Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 230000004888 barrier function Effects 0.000 description 5
- 229940125898 compound 5 Drugs 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- HNZUKQQNZRMNGS-UHFFFAOYSA-N 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine Chemical class BrC1=CC=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HNZUKQQNZRMNGS-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
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- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 2
- ZHQNDEHZACHHTA-UHFFFAOYSA-N 9,9-dimethylfluorene Chemical class C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 ZHQNDEHZACHHTA-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
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- 238000007872 degassing Methods 0.000 description 2
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- ASUOLLHGALPRFK-UHFFFAOYSA-N phenylphosphonoylbenzene Chemical class C=1C=CC=CC=1P(=O)C1=CC=CC=C1 ASUOLLHGALPRFK-UHFFFAOYSA-N 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 238000013519 translation Methods 0.000 description 2
- 230000014616 translation Effects 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- OIRHKGBNGGSCGS-UHFFFAOYSA-N 1-bromo-2-iodobenzene Chemical compound BrC1=CC=CC=C1I OIRHKGBNGGSCGS-UHFFFAOYSA-N 0.000 description 1
- MSTJGWCHJCZPEQ-UHFFFAOYSA-N 2-(2-bromophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound BrC1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 MSTJGWCHJCZPEQ-UHFFFAOYSA-N 0.000 description 1
- ZKGHGKNHPPZALY-UHFFFAOYSA-N 9-(3-bromophenyl)carbazole Chemical compound BrC1=CC=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=C1 ZKGHGKNHPPZALY-UHFFFAOYSA-N 0.000 description 1
- PKDVNRITKFAVFU-UHFFFAOYSA-N CC1(C=CC=C2C=C3C(C=C4C5=CC=CC=C5C5=CC=CC=C5C4=C3)=C12)C Chemical group CC1(C=CC=C2C=C3C(C=C4C5=CC=CC=C5C5=CC=CC=C5C4=C3)=C12)C PKDVNRITKFAVFU-UHFFFAOYSA-N 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 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
- 239000013078 crystal Substances 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- QPJORFLSOJAUNL-UHFFFAOYSA-N dibenzo[a,d][7]annulene Chemical compound C1=CC2=CC=CC=C2CC2=CC=CC=C21 QPJORFLSOJAUNL-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000004776 molecular orbital Methods 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000007781 pre-processing Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/20—Spiro-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/20—Spiro-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/20—Spiro-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D517/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms
- C07D517/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms in which the condensed system contains three hetero rings
- C07D517/20—Spiro-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D517/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms
- C07D517/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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Abstract
本发明公开一种衍生自7',7'‑二甲基‑5',7'‑二氢螺[环戊[1,2‑b:5,4‑b']二噻吩‑4,13'‑茚并[1,2‑b]吖啶]核心结构的新颖多杂芳族化合物。该多杂芳族化合物可用作有机电激发光材料用于有机电激发光元件和电子设备。
Description
技术领域
本发明是关于一种具有7',7'-二甲基-5',7'-二氢螺[环戊[1,2-b:5,4-b']二噻吩-4,13'-茚并[1,2-b]吖啶]核心结构的多杂芳族化合物,更具体言之是关于一种使用该多杂芳族化合物的有机电激发光元件。
背景技术
有机电激发光(有机EL)元件是一种有机发光二极体(LED),其中发光层是由有机化合物制成的膜,有机化合物可响应电流而发光。包含有机化合物的发光层被夹置于两个电极之间。有机EL元件由于其高照度、重量轻、超薄外形、自照明而无需背光、低功耗、广视角、高对比、制造方法简单以及反应时间快速而被应用于平板显示器。
1987年在伊士曼柯达(Eastman Kodak)公司的邓青云(Ching W.Tang)和史蒂芬范斯莱克(Steven Van Slyke)报导出第一个二极体元件。该元件使用具有单独的电洞传输层和电子传输层的双层结构,使得复合和发光在有机层的中间发生。此举造成操作电压降低并且效率提高,从而引领当今主流的有机EL元件研究及元件生产。
典型上,有机EL是由位于两个电极之间的有机材料层构成。有机材料层包括电洞传输层(hole transporting layer,HTL)、发光层(emitting layer,EML)、及电子传输层(electron transporting layer,ETL)。有机电激发光的基本机制涉及载子(carrier)的注入、传输、及复合以及激子(exciton)的形成,以进行发光。当施加外部电压到有机EL元件时,电子和电洞分别从阴极和阳极注入。电子从阴极注入最低未占用分子轨道(lowestunoccupied molecular orbital,LUMO)中,而电洞从阳极注入最高占用分子轨道(highestoccupied molecular orbital,HOMO)中。随后,电子在发光层中与电洞重组而形成激子,然后激子失活而发光。当发光分子吸收能量而达到激发态时,依据电子和电洞的自旋组合,激子可呈单重态或三重态。众所周知,在电激发下形成的激子通常包括25%的单重态激子和75%的三重态激子。然而,在荧光材料中,75%的三重态激子中的电生成能量将作为热量消散,因为从三重态衰减是自旋禁阻(spin forbidden)的。因此,荧光电激发光元件仅具有25%的内部量子效率(internal quantumefficiency),导致理论上最高的外部量子效率(EQE)仅有5%,因为元件的光输出耦合效率只有约20%。相较于荧光电激发光元件,磷光有机EL元件利用自旋─轨道相互作用(spin-orbit interacttion)来促进单重态与三重态之间的系统间穿越(intersystem crossing),因此来自单重态和三重态的发光皆可取得,而且电激发光元件的内部量子效率可自25%升至100%。
在2012年,安达教授(Adachi)和其同事开发出一种新型荧光有机EL元件。此新型有机EL元件体现热活化延迟荧光(thermally activated delayed fluorescence,TADF)机制,其是一种有希望经由反向系统间穿越(reverse intersystem crossing,RISC)机制,借由将自旋禁阻的三重态激子转化至单重态能阶以获得高比例的单重态激子形成的方式。
三重态及单重态激子均能被磷光有机EL元件利用。由于与单重态激子相比,三重态激子具有较长的寿命和扩散距离,故磷光有机EL元件通常需要在发光层(EML)与电子传输层(ETL)之间设置附加的电洞阻挡层(HBL)或以具有电洞阻挡能力的电子传输层(HBETL)取代典型的ETL。使用HBL或HBETL的目的是为了将注入电洞与电子的复合及生成激子的松弛(relaxation)局限在发光层内,因此能够提升元件的效率。为了满足这些作用,电洞阻挡材料必须具有适合阻止电洞从发光层移到电子传输层并使电子从电子传输层移到发光层的HOMO(最高占用分子轨道)和LUMO(最低未占用分子轨道)能阶。除此之外,还需要磷光发射主体材料具有良好的热和电化学稳定性。
具有10H-螺[吖啶-9,9'-芴]结构的化合物已经在有机EL元件上找到用途,此可见于美国专利第8,632,893号。此外,具有7',7'-二甲基-5',7',10,11-四氢螺[二苯并[a,d][7]轮烯-5,13'-茚并[1,2-b]吖啶]结构的化合物被用于OLED,其由韩国专利申请号1020100029865公开。在本发明中,我们开发出具有7',7'-二甲基-5',7'-二氢螺[环戊[1,2-b:5,4-b']二噻吩-4,13'-茚并[1,2-b]吖啶]核心结构的新颖多杂芳族化合物,用以改善有机EL元件的性能。
发明内容
本发明的目的是提供一种多杂芳族化合物及使用该多杂芳族化合物的有机EL元件,该有机EL元件能够在降低的电压下操作并且表现出高的发光效率。
本发明的另一目的是提供一种多杂芳族化合物,该多杂芳族化合物可用作发光层中的磷光主体材料、荧光主体材料、荧光掺杂材料、TADF主体材料、或TADF掺杂材料、及/或有机EL元件的电子传输层(ETL)材料,以改善功耗和发光效率。
依据本发明,一种可用于有机EL元件的多杂芳族化合物被公开。该多杂芳族化合物是由下式(1)表示:
其中X为O、S、或Se;n和p各自独立为0至2的整数;L表示以下式(2):
并且B表示以下式(3):
其中m为0至4的整数;Y为O、S、Se、CR6R7、NR8或SiR9R10;以及R1至R11独立选自由氢原子、卤化物、具有1至60个碳原子的经取代或未经取代的烷基、具有6至60个碳原子的经取代或未经取代的芳基、具有6至60个碳原子的经取代或未经取代的芳烷基、具有3至60个碳原子的经取代或未经取代的杂芳基、及具有6至60个碳原子的经取代或未经取代的芳胺基所组成的群组。
本发明进一步公开了一种有机电激发光元件。该有机电激发光元件包含由阴极和阳极组成的一电极对、及在该电极对之间的一发光层及一个或多个有机薄膜层。该发光层和该有机薄膜层中的至少一个包含式(1)的多杂芳族化合物。
附图说明
图1显示本发明的有机EL元件的一个实施例。在该元件中,电洞注入层7沉积在透明电极6上,电洞传输层8沉积在电洞注入层7上,荧光或磷光发光层9沉积在电洞传输层8上,电洞阻挡层10沉积在发光层9上,电子传输层11沉积在电洞阻挡层10上,电子注入层12沉积在电子传输层11上,以及金属电极13沉积在电子注入层12上。
6透明电极 7电洞注入层
8电洞传输层 9发光层
10电洞阻挡层 11电子传输层
12电子注入层 13金属电极。
具体实施方式
本发明探究多杂芳族化合物及使用该多杂芳族化合物的有机电激发光元件(有机EL元件)。下面将详细说明生产、结构及组成部分,以使本发明可被充分理解。本发明的应用显然不受限于本领域技术人员熟知的具体细节。另一方面,不对众所周知的一般组成部分和过程作详细描述,以避免对本发明造成不必要的限制。现在将在下面更详细地描述本发明的一些较佳实施例。然而,应当理解的是,除了本文明确描述的实施例之外,本发明还可实施于各种其他实施例中,也就是说,本发明还可被广泛应用于其他实施例,且本发明的范围不会因此受到明确的限制,只受随附申请专利范围的内容限制。
在本发明的一个实施例中,公开了可以用作发光层的主体材料、荧光掺杂材料、热活化延迟荧光主体材料、或热活化延迟荧光掺杂材料、及/或有机EL元件的电子传输材料的多杂芳族化合物。该多杂芳族化合物由下式(1)表示:
其中X为O、S、或Se;n和p各自独立为0至2的整数;L表示以下式(2):
并且B表示以下式(3):
其中m为0至4的整数;Y为O、S、Se、CR6R7、NR8或SiR9R10;以及R1至R11独立选自由氢原子、卤化物、具有1至60个碳原子的经取代或未经取代的烷基、具有6至60个碳原子的经取代或未经取代的芳基、具有6至60个碳原子的经取代或未经取代的芳烷基、具有3至60个碳原子的经取代或未经取代的杂芳基、及具有6至60个碳原子的经取代或未经取代的芳胺基所组成的群组。
在一些实施例中,R1至R11独立选自由氢原子、卤化物、具有1至6个碳原子的经取代或未经取代的烷基、具有6至36个碳原子的经取代或未经取代的芳基、具有7至17个碳原子的经取代或未经取代的芳烷基、具有3至47个碳原子的经取代或未经取代的杂芳基、及具有6至37个碳原子的经取代或未经取代的芳胺基所组成的群组。
在一些实施例中,R1选自氢原子;R2和R3独立选自氢原子、具有1至6个碳原子的经取代或未经取代的烷基、具有6至12个碳原子的经取代或未经取代的芳烷基、及具有6至37个碳原子(优选6-12个碳原子)的经取代或未经取代的芳胺基所组成的群组;R4选自氢原子、具有1至6个碳原子的经取代或未经取代的烷基、具有6至24个碳原子(优选具有6至14个碳原子)的经取代或未经取代的芳基、具有3至47个碳原子(优选3-40个碳原子)的经取代或未经取代的杂芳基、及具有6至37个碳原子(优选19-37个碳原子)的经取代或未经取代的芳胺基所组成的群组;R5选自氢原子;R6和R7独立选自氢原子、具有1至6个碳原子的经取代或未经取代的烷基;R8选自具有6至12个碳原子的经取代或未经取代的芳烷基、具有6个碳原子的经取代或未经取代的芳基、具有3至47个碳原子(优选4-18个碳原子)的经取代或未经取代的杂芳基;R9和R10独立选自具有6至12个碳原子(优选7个碳原子)的经取代或未经取代的芳烷基、具有6个碳原子的经取代或未经取代的芳基;R11选自氢原子、具有1至6个碳原子的经取代或未经取代的烷基、具有7至17个碳原子的经取代或未经取代的芳烷基、具有6至24个碳原子的经取代或未经取代的芳基、具有3至47个碳原子(优选3-46个碳原子)的经取代或未经取代的杂芳基、及具有6至37个碳原子(优选19-37个碳原子)的经取代或未经取代的芳胺基所组成的群组。
当所述烷基、芳基、芳烷基、杂芳基和芳胺基各自独立地被取代时,取代基可以各自独立的选自具有1至6个碳原子的烷基、具有6至18个碳原子的芳基、具有12至40个碳原子的杂芳基、和具有25至37个碳原子的芳胺基所组成的群组。
本发明所述的芳烷基包括如下两种情况:其中A表示芳基,B表示烷基。
在一些实施例中,R8或R11表示以下取代基中之一:
优选地,该多杂芳族化合物由以下式(4)至式(9)中之一表示:
其中X、n、p、L、m、Y、及R1至R11具有与上述定义相同的含义。
优选地,该多杂芳族化合物为以下化合物中之一:
在本发明的另一个实施例中,公开了一种有机电激发光元件。该有机电激发光元件包含由阴极和阳极组成的一电极对、及在该电极对之间的一发光层及一个或多个有机薄膜层。该发光层和该有机薄膜层中的至少一个包含式(1)的多杂芳族化合物。
在一些实施例中,包含式(1)的多杂芳族化合物的发光层为一主体材料。该主体材料可以是磷光主体材料或荧光主体材料。在某些实施例中,包含式(1)的多杂芳族化合物的发光层被用作一荧光掺杂材料。
在一些实施例中,包含式(1)的多杂芳族化合物的发光层为一热活化延迟荧光主体材料。在其他实施例中,包含式(1)的多杂芳族化合物的发光层被用作一热活化延迟荧光掺杂材料。在一些实施例中,包含式(1)的多杂芳族化合物的有机薄膜层为一电子传输层。
在本发明的另一实施例中,该有机电激发光元件为一发光面板。在本发明的其他实施例中,该有机电激发光元件为一背光面板。
将借由以下的示例性实施例来清楚阐明本发明的多杂芳族化合物的详细制备,但本发明并不限于这些示性实施例。实施例1至实施例7说明本发明的多杂芳族化合物的制备,而实施例8说明有机EL元件的制造及测试报告。
实施例1
N-(2-溴苯基)-9,9-二甲基-9H-芴-2-胺的合成
将10g(35.3mmol)的1-溴-2-碘苯、7.4g(35.3mmol)的9,9-二甲基-9H-芴-2-胺、0.52g(0.7mmol)的Pd(dppf)Cl2、6.8g(70.6mmol)的叔丁醇钠、及60ml的甲苯的混合物除气并置于氮气下,然后在100℃加热2小时。反应完成后,使混合物冷却至室温,然后过滤移除溶剂。粗产物以柱层析纯化,得到9.4g的黄色固体(73%)。1H NMR(CDCl3,400MHz):化学位移(ppm)8.11(d,1H),7.65(d,1H),7.55(d,2H),7.43(m,1H),7.31(m,1H),7.18(m,2H),6.68-6.74(m,2H),6.50-6.56(m,2H),4.11(s,1H),1.68(s,6H)。
7',7'-二甲基-5',7'-二氢螺[环戊[1,2-b:5,4-b']二噻吩-4,13'-茚并[1,2-b]吖啶]的合成
将5g(13.7mmol)的N-(2-溴苯基)-9,9-二甲基-9H-芴-2-胺和100ml的THF的混合物在干冰浴中冷却,之后滴加8.2ml的正丁基锂(2.5M溶于己烷,20.6mmol),然后在干冰浴中搅拌1小时。之后,滴加2.9g溶于20ml THF的4H-环戊[1,2-b:5,4-b']-二噻吩-4-酮,并在室温下搅拌1小时,然后在70℃加热12小时。减压移除混合物中的溶剂。随后,加入1.58g的甲磺酸和50ml的CHCl3,然后在60℃搅拌2小时。反应完成后,使混合物冷却至室温并移除溶剂。以柱层析纯化粗产物,得到1.64g的棕色固体(26%)。1H NMR(CDCl3,400MHz):化学位移(ppm)8.05(d,1H),7.61(m,3H),7.44(d,2H),7.27-7.33(m,1H),6.92-7.01(m,4H),6.64-6.68(m,2H),6.48(d,H),4.13(s,1H),1.66(s,6H)。
化合物C3的合成
将1g(2.18mmol)的7',7'-二甲基-5',7'-二氢螺[环戊[1,2-b:5,4-b']二噻吩-4,13'-茚并[1,2-b]吖啶]、0.93g(2.39mmol)的2-(3-溴苯基)-4,6-二苯基-1,3,5-三嗪、0.04g(0.04mmol)的Pd2(dba)3、0.31g(3.27mmol)的叔丁醇钠、及30ml的邻二甲苯的混合物除气并置于氮气下,然后在120℃加热3小时。反应完成后,使混合物冷却至室温。随后,将50ml的甲醇加到混合物中,然后过滤并用甲醇洗涤,得到1.13g的黄色固体(68%)。1H NMR(CDCl3,400MHz):化学位移(ppm)8.35(d,4H),7.93(d,1H),7.69(d,1H),7.52-7.59(m,7H),7.34-7.42(m,6H),7.26(m,1H),6.96-7.02(m,3H),6.86(d,1H),6.61-6.67(d,3H),6.52(d,1H),1.69(s,6H)。MS(m/z,EI+):766.7。
实施例2
化合物C12的合成
使用与实施例1相同的合成过程,不同之处仅在于使用12-(3-溴苯基)-4,6-二苯基嘧啶取代2-(3-溴苯基)-4,6-二苯基-1,3,5-三嗪,得到化合物5'-(3-(4,6-二苯基嘧啶-2-基)苯基)-7',7'-二甲基-5',7'-二氢螺[环戊[1,2-b:5,4-b']二噻吩-4,13'-茚并[1,2-b]吖啶]。MS(m/z,EI+):765.6。
实施例3
化合物C5的合成
使用与实施例1相同的合成过程,不同之处仅在于使用9-(3-溴苯基)-9H-咔唑取代2-(3-溴苯基)-4,6-二苯基-1,3,5-三嗪,得到所需化合物5'-(3-(9H-咔唑-9-基)苯基)-7',7'-二甲基-5',7'-二氢螺[环戊[1,2-b:5,4-b']二噻吩-4,13'-茚并[1,2-b]吖啶]。MS(m/z,EI+):700.6。
实施例4
化合物C7的合成
使用与实施例1相同的合成过程,不同之处仅在于使用2-溴二苯并[b,d]噻吩取代2-(3-溴苯基)-4,6-二苯基-1,3,5-三嗪,得到所需化合物5'-(二苯并[b,d]噻吩-2-基)-7',7'-二甲基-5',7'-二氢螺[环戊[1,2-b:5,4-b']二噻吩-4,13'-茚并[1,2-b]吖啶]。MS(m/z,EI+):641.5。
实施例5
化合物C8的合成
使用与实施例1相同的合成过程,不同之处仅在于使用2-溴-9,9-二甲基-9H-芴取代2-(3-溴苯基)-4,6-二苯基-1,3,5-三嗪,得到所需化合物5'-(9,9-二甲基-9H-芴-2-基)-7',7'-二甲基-5',7'-二氢螺[环戊[1,2-b:5,4-b']二噻吩-4,13'-茚并[1,2-b]吖啶]。MS(m/z,EI+):651.6。
实施例6
化合物C6的合成
使用与实施例1相同的合成过程,不同之处仅在于使用6-溴-9,9'-二苯基-9H,9'H-3,3'-双咔唑取代2-(3-溴苯基)-4,6-二苯基-1,3,5-三嗪,得到所需化合物5'-(9,9'-二苯基-9H,9'H-[3,3'-双咔唑-6-基)-7',7'-二甲基-5',7'-二氢螺[环戊[1,2-b:5,4-b']二噻吩-4,13'-茚并[1,2-b]吖啶]。MS(m/z,EI+):942.1。
实施例7
化合物C1的合成
使用与实施例1相同的合成过程,不同之处仅在于使用1-溴萘取代2-(3-溴苯基)-4,6-二苯基-1,3,5-三嗪,得到所需化合物7',7'-二甲基-5'-(萘-1-基)-5',7'-二氢螺[环戊[1,2-b:5,4-b']二噻吩-4,13'-茚并[1,2-b]吖啶]。MS(m/z,EI+):585.6。
生产有机电激发光元件的一般方法
提供阻值为9~12欧姆/平方(ohm/square)及厚度为120~160nm的铟锡氧化物涂层玻璃(以下称为ITO基板),并在超声波浴(例如洗涤剂、去离子水)中进行多步骤清洗。在气相沉积有机层之前,借由紫外光(UV)和臭氧进一步处理清洗过的ITO基板。ITO基板的所有预处理过程都在洁净室(100级)内进行。
在高真空设备下(10-7Torr)利用电阻加热的石英舟以气相沉积将这些有机层依次涂布到ITO基板上。借助石英晶体监视器来精确监控或设定各层的厚度和气相沉积速率(0.1~0.3nm/sec)。如上所述,还可以使个别层包含不只一种化合物,即通常掺杂有掺杂材料的主体材料。此可借由来自两个或多个来源的共气相沉积成功地实现,表示本发明的多杂芳族化合物是热稳定的。
使用二吡嗪并[2,3-f:2',3'-h]喹喔啉-2,3,6,7,10,11-六腈(dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile)(HAT-CN)形成有机EL元件的电洞注入层。使用N,N-双(萘-1-基)-N,N-双(苯基)-联苯胺(NPB)形成电洞传输层。使用双(2-苯基吡啶)(2,4-二苯基吡啶)-铱(III)(D1)作为磷光掺杂剂,并使用3-(9,9-二甲基吖啶-10(9H)-基)-9H-呫吨-9-酮(D2)作为荧光掺杂剂。使用4-(10,10-二甲基-10H-茚并[2,1-b]三亚苯-13-基)二苯并[b,d]噻吩(H1)作为磷光主体材料,并且使用二苯并[b,d]噻吩-2,8-二基双(二苯基氧化膦)(H2)作为荧光主体材料和TADF主体材料。使用2-(10,10-二甲基-10H-茚并[2,1-b]三亚苯-13-基)-9-苯基-1,10-啡啉(ET1)作为电子传输材料。使用化合物C12、C198作为荧光掺杂材料来与化合物D2比较,并且使用化合物C3作为TADF掺杂材料来与化合物A比较。使用化合物C5、C7、C56、C117、C130、及C137作为磷光主体材料来与化合物H1比较。将化合物C8、C91、C93、C104、及C155用作荧光主体材料与化合物H2进行比较,并将化合物C6用作TADF主体材料与化合物H2进行比较。使用化合物C1作为电子传输材料来与化合物ET1进行比较。本发明中用于制作对照和示例性有机EL元件的传统OLED材料和本发明的示例性多杂芳族化合物的化学结构如下所示:
有机EL元件一般包含透过热蒸发形成为阴极的低功函数金属,例如Al、Mg、Ca、Li及K,且该低功函数金属可有助于电子从阴极注入电子传输层。另外,在阴极与电子传输层之间引入薄膜电子注入层,用于降低电子注入阻障并改善有机EL元件的性能。熟知的电子注入层材料为具有低功函数的金属卤化物或金属氧化物,例如:LiF、LiQ(如下所示)、MgO、或Li2O。另一方面,在制作有机EL元件之后,透过使用PR650光谱扫描光谱仪量测EL光谱及CIE座标。此外,使用吉时利(Keithley)2400可程序化电压电流源测得电流/电压、亮度/电压、及效率/电压特性。在室温(约25℃)及大气压下操作上述设备。
实施例8
使用与上述一般方法类似的过程制作发射绿光并具有以下如图1所示元件结构的有机EL元件:ITO/HAT-CN(20nm)/NPB(130nm)/掺杂有掺杂剂的主体(30nm)/ETM/LiQ/Al(160nm)。将这些有机EL元件的I-V-B(在1000尼特下)测试报告总结于下表1。
表1
掺杂剂(%) | 主体 | ETM | 电压(V) | 效率(cd/A) |
D1(8%) | H1 | ET1 | 4.9 | 14 |
D1(8%) | C5 | ET1 | 4.6 | 20 |
D1(8%) | C7 | ET1 | 4.8 | 16 |
D1(8%) | C56 | ET1 | 4.7 | 17 |
D1(8%) | C117 | ET1 | 4.8 | 15 |
D1(8%) | C130 | ET1 | 4.7 | 16 |
D1(8%) | C137 | ET1 | 4.8 | 16 |
D2(20%) | H2 | ET1 | 5.1 | 11 |
D2(20%) | C8 | ET1 | 4.7 | 13 |
D2(20%) | C91 | ET1 | 5.0 | 13 |
D2(20%) | C93 | ET1 | 4.8 | 12 |
D2(20%) | C104 | ET1 | 4.7 | 14 |
D2(20%) | C155 | ET1 | 5.0 | 12 |
C12(20%) | H2 | ET1 | 4.9 | 15 |
C198(20%) | H2 | ET1 | 5.0 | 14 |
A(20%) | H2 | ET1 | 5 | 10 |
A(20%) | C6 | ET1 | 4.8 | 13 |
C3(20%) | H2 | ET1 | 4.7 | 22 |
C3(20%) | H2 | C1 | 4.5 | 25 |
根据上述有机EL元件的测试报告总结,显而易见的是,用作有机EL元件的荧光或TADF掺杂材料、磷光、荧光或TADF主体材料、或电子传输材料的式(1)多杂芳族化合物表现出比现有技术的材料更佳的性能。具体来说,本发明使用式(1)的多杂芳族化合物作为掺杂材料、主体材料或电子传输材料来与主体材料H2或掺杂材料D1、D2或化合物A搭配的有机EL元件可具有更低的功耗和更高的发光效率。
总而言之,本发明公开了多杂芳族化合物,该多杂芳族化合物可在有机EL元件中用作发光层的主体材料、荧光掺杂材料、热活化延迟荧光主体材料或热活化延迟荧光掺杂材料、或电子传输材料。所述的多杂芳族化合物由下式(1)表示:
其中X为O、S、或Se;n和p各自独立为0至2的整数;L表示以下式(2):
并且B表示以下式(3):
其中m为0至4的整数;Y为O、S、Se、CR6R7、NR8或SiR9R10;以及R1至R11独立选自由氢原子、卤化物、具有1至60个碳原子的经取代或未经取代的烷基、具有6至60个碳原子的经取代或未经取代的芳基、具有6至60个碳原子的经取代或未经取代的芳烷基、具有3至60个碳原子的经取代或未经取代的杂芳基、及具有6至60个碳原子的经取代或未经取代的芳胺基所组成的群组。
根据上述教导显然可以作出许多的修改及变化。因此,应当了解的是,在随附申请专利范围的范围内,可以以本文具体描述的方式以外的其他方式来实施本发明。虽然,本文中已说明并描述了具体实施例,但对于本领域技术人员来说,显而易见的是可以在不偏离欲单独由随附申请专利范围限制的情况下对本发明作出许多修改。
Claims (13)
1.一种以下式(1)的多杂芳族化合物:
其中X为O、S、或Se;n和p各自独立为0至2的整数;L表示以下式(2):
并且B表示以下式(3):
其中m为0至4的整数;Y为O、S、Se、CR6R7、NR8、或SiR9R10;以及R1至R11独立选自由氢原子、卤化物、具有1至60个碳原子的经取代或未经取代的烷基、具有6至60个碳原子的经取代或未经取代的芳基、具有6至60个碳原子的经取代或未经取代的芳烷基、具有3至60个碳原子的经取代或未经取代的杂芳基、及具有6至60个碳原子的经取代或未经取代的芳胺基所组成的群组;优选R1至R11独立选自由氢原子、卤化物、具有1至6个碳原子的经取代或未经取代的烷基、具有6至36个碳原子的经取代或未经取代的芳基、具有7至17个碳原子的经取代或未经取代的芳烷基、具有3至47个碳原子的经取代或未经取代的杂芳基、及具有6至37个碳原子的经取代或未经取代的芳胺基所组成的群组。
2.如权利要求1所述的多杂芳族化合物,其中R8或R11表示以下取代基中之一的取代基:
3.如权利要求1所述的多杂芳族化合物,其中该多杂芳族化合物由以下式(4)至式(9)中之一表示:
其中X、n、p、L、m、Y及R1至R11与权利要求1所定义的含义相同。
4.如权利要求3所述的多杂芳族化合物,其中R8或R11表示以下取代基中之一的取代基:
5.如权利要求1所述的多杂芳族化合物,其中该多杂芳族化合物为以下化合物中之一的化合物:
6.一种有机电激发光元件,包含由阴极和阳极组成的一电极对、及在该电极对之间的一发光层及一个或多个有机薄膜层,其中该发光层和该有机薄膜层中的至少一个包含如权利要求1所述的多杂芳族化合物。
7.如权利要求6所述的有机电激发光元件,其中包含式(1)的多杂芳族化合物的发光层为一主体材料。
8.如权利要求6所述的有机电激发光元件,其中包含式(1)的多杂芳族化合物的发光层为一荧光掺杂材料。
9.如权利要求6所述的有机电激发光元件,其中包含式(1)的多杂芳族化合物的发光层为一热活化延迟荧光主体材料。
10.如权利要求6所述的有机电激发光元件,其中包含式(1)的多杂芳族化合物的发光层为一热活化延迟荧光掺杂材料。
11.如权利要求6所述的有机电激发光元件,其中包含式(1)的多杂芳族化合物的有机薄膜层为一电子传输层。
12.如权利要求6所述的有机电激发光元件,其中该有机电激发光元件为一发光面板。
13.如权利要求6所述的有机电激发光元件,其中该有机电激发光元件为一背光面板。
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CN113527297A (zh) * | 2021-07-19 | 2021-10-22 | 上海天马有机发光显示技术有限公司 | 一种有机化合物及其应用 |
CN115583887A (zh) * | 2022-09-23 | 2023-01-10 | 吉林奥来德光电材料股份有限公司 | 一种有机电致发光化合物及其制备方法和应用 |
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