CN104892578B - Fluorenes spiral shell triphenylamine derivative and application thereof - Google Patents
Fluorenes spiral shell triphenylamine derivative and application thereof Download PDFInfo
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- CN104892578B CN104892578B CN201510255055.1A CN201510255055A CN104892578B CN 104892578 B CN104892578 B CN 104892578B CN 201510255055 A CN201510255055 A CN 201510255055A CN 104892578 B CN104892578 B CN 104892578B
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- 125000006617 triphenylamine group Chemical group 0.000 title abstract description 20
- 150000002220 fluorenes Chemical class 0.000 title abstract 5
- 239000000463 material Substances 0.000 claims abstract description 38
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 10
- 239000000126 substance Substances 0.000 claims abstract description 5
- 238000001704 evaporation Methods 0.000 claims description 21
- 230000008020 evaporation Effects 0.000 claims description 21
- 239000011521 glass Substances 0.000 claims description 21
- 239000011248 coating agent Substances 0.000 claims description 16
- 238000000576 coating method Methods 0.000 claims description 16
- 238000007738 vacuum evaporation Methods 0.000 claims description 16
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 claims description 12
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 claims description 12
- 230000005540 biological transmission Effects 0.000 claims description 11
- IWZZBBJTIUYDPZ-DVACKJPTSA-N (z)-4-hydroxypent-3-en-2-one;iridium;2-phenylpyridine Chemical compound [Ir].C\C(O)=C\C(C)=O.[C-]1=CC=CC=C1C1=CC=CC=N1.[C-]1=CC=CC=C1C1=CC=CC=N1 IWZZBBJTIUYDPZ-DVACKJPTSA-N 0.000 claims description 9
- 238000002347 injection Methods 0.000 claims description 9
- 239000007924 injection Substances 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000000975 dye Substances 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 8
- 230000004888 barrier function Effects 0.000 claims description 7
- 230000000903 blocking effect Effects 0.000 claims description 7
- 239000008367 deionised water Substances 0.000 claims description 5
- 229910021641 deionized water Inorganic materials 0.000 claims description 5
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 4
- 239000003599 detergent Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims 1
- 150000001716 carbazoles Chemical class 0.000 abstract description 11
- 230000009477 glass transition Effects 0.000 abstract description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 abstract description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 6
- 238000005401 electroluminescence Methods 0.000 abstract description 5
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 abstract description 5
- 230000021615 conjugation Effects 0.000 abstract description 3
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 abstract description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 3
- KYUIIGJSSHTWDW-UHFFFAOYSA-N 2,3-dimethoxy-n-phenylaniline Chemical class COC1=CC=CC(NC=2C=CC=CC=2)=C1OC KYUIIGJSSHTWDW-UHFFFAOYSA-N 0.000 abstract description 2
- OYFFSPILVQLRQA-UHFFFAOYSA-N 3,6-ditert-butyl-9h-carbazole Chemical class C1=C(C(C)(C)C)C=C2C3=CC(C(C)(C)C)=CC=C3NC2=C1 OYFFSPILVQLRQA-UHFFFAOYSA-N 0.000 abstract description 2
- MRPZLXMWCIWOGP-UHFFFAOYSA-N 2,3-dimethyl-n-phenylaniline Chemical class CC1=CC=CC(NC=2C=CC=CC=2)=C1C MRPZLXMWCIWOGP-UHFFFAOYSA-N 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 73
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical class ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 17
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 12
- 229910052741 iridium Inorganic materials 0.000 description 11
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 7
- 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 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
- 150000005360 2-phenylpyridines Chemical class 0.000 description 4
- -1 4,6- difluorophenyl Chemical group 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000003208 petroleum 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
- 239000004305 biphenyl Substances 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 238000002242 deionisation method Methods 0.000 description 3
- 125000000950 dibromo group Chemical group Br* 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000005611 electricity Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- UEMGWPRHOOEKTA-UHFFFAOYSA-N 1,3-difluorobenzene Chemical class FC1=CC=CC(F)=C1 UEMGWPRHOOEKTA-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 description 1
- DKFPQCUHILRPNN-UHFFFAOYSA-N 2-(4-methylphenyl)thiophene Chemical class C1=CC(C)=CC=C1C1=CC=CS1 DKFPQCUHILRPNN-UHFFFAOYSA-N 0.000 description 1
- KDOKHBNNNHBVNJ-UHFFFAOYSA-N C1=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12.N1C=CC=CC=C1 Chemical class C1=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12.N1C=CC=CC=C1 KDOKHBNNNHBVNJ-UHFFFAOYSA-N 0.000 description 1
- 241000283074 Equus asinus Species 0.000 description 1
- 244000283207 Indigofera tinctoria Species 0.000 description 1
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical class BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- UNRQTHVKJQUDDF-UHFFFAOYSA-N acetylpyruvic acid Chemical compound CC(=O)CC(=O)C(O)=O UNRQTHVKJQUDDF-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- DZBUGLKDJFMEHC-UHFFFAOYSA-N benzoquinolinylidene Natural products C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 150000008376 fluorenones Chemical class 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- CECAIMUJVYQLKA-UHFFFAOYSA-N iridium 1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 CECAIMUJVYQLKA-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- DYFFAVRFJWYYQO-UHFFFAOYSA-N n-methyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(C)C1=CC=CC=C1 DYFFAVRFJWYYQO-UHFFFAOYSA-N 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000005395 radioluminescence Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000004017 vitrification Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/20—Spiro-condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
Abstract
The invention discloses fluorenes spiral shell triphenylamine derivative and application thereof, described fluorenes spiral shell triphenylamine derivative chemical constitution is as follows：；Wherein, fluorenes spiral shell triphenylamine is main body；A is carbazole, the miscellaneous carbazoles of α N, the miscellaneous carbazoles of β N, the miscellaneous carbazoles of γ N, pyridine, diphenylamines, dimethoxy diphenylamines, dimethyl diphenylamines or 3,6 di-t-butyl carbazoles.The fluorenes spiral shell triphenylamine derivative of the present invention has good heat endurance and P-conductivity, pass through straightforward procedure, efficiently control material of main part conjugation degree, increase compound molecular weight, the triplet energy level of material and glass transition temperature has been obtained large increase, and significantly reduce cut-in voltage.Polarity can be adjusted by push/pull electron group, and the intensity by adjusting its push-and-pull electronics group is allowed to the raising of bipolarity performance, and compared with conventional phosphorescent light body material, device performance is improved, and can be widely applied to field of organic electroluminescence.
Description
Technical field
The invention belongs to organic photoelectrical material technical field, and in particular to a kind of fluorenes spiral shell triphenylamine derivative and application thereof.
Background technology
Organic electroluminescent is a kind of selfluminous element, by clipping luminescent layer between a pair of electrodes and applying voltage, from
Negative electrode（First electrode）Injected electrons and anode（Second electrode）Injected holes is compounded to form molecular exciton in the centre of luminescence,
And the molecular exciton is released energy when returning to ground state to light.Organic electroluminescence device has that voltage is low, brightness is high, regards
Angular width, the characteristics such as fast, thermal adaptability is good are responded, be widely used in the electronic product display such as television set, mobile phone, MP3.
Electroluminescent organic material is generally divided into singlet fluorescent dye and triplet state phosphorescent coloring, wherein due to singlet
Fluorescence can only utilize 25% exciton, 75% exciton all due to transition speed can not radioluminescence, and triplet state phosphorescence lights
But 100% exciton can be utilized, makes luminous efficiency considerably beyond singlet fluorescence radiation but triplet emitter highly concentrated
Stronger concentration quenching effect is had when spending, the luminous efficiency of luminescent layer can be reduced, causes organic luminescent device performance relatively low.Cause
This, uses Subjective and Objective structure, i.e., by fluorescent dye or phosphorescent coloring with certain mostly in present organic electroluminescence device
Doped in concentrations profiled, to avoid burying in oblivion for concentration quenching and triplet-triplet, improves device performance in main substance.Nowadays, it is existing
There is technology to disclose many kinds of substance as material of main part.Forrest and Thompson in 1999 etc.（M. A. Baldo, S.
Lamansky, P. E. Burroes, M. E. Thompson, S. R. Forrest. Appl. Phys. Lett.,
1999, 75, 4）By green phosphorescent material Ir (ppy) 3 with 6wt% doped in concentrations profiled in 4,4 '-N, the carbazoles of N '-two-biphenyl
（CBP）Material of main part in, the green glow OLED maximums external quantum efficiency of acquisition is up to 10%.But CBP triplet excited state energy
There are 2.56 eV, if being doped with the blue phosphor materials of high triplet excitation energy, it may occur that energy returns to showing for main body
As making the external quantum efficiency of device drop to 5.7%.In order to further improve the efficiency of blue phosphorescent device, it is necessary to using high by three
The material of main part of state energy is weighed, then Forrest in 2003（Holmes, R. J. Forrest, S. R. Tung, Y.-J.
Kwong, R. C. and Brown, J. J. Garon, S. Thompson, M. E., Appl Phys Let, 2003,
82, 2422）Develop N, the carbazyl -3,5- substituted benzenes of N '-two（mCP）, this material is to reduce CBP conjugated system, double
State energy rises to 2.9eV, and external quantum efficiency is promoted to 7.8%.But mCP glass transition temperature is relatively low, and material sheet
Body stability is not high, hinders its extensive use.
The content of the invention
Technical problems to be solved：It is an object of the invention to provide one kind to have high triplet energies, and high-vitrification turns
The blue phosphorescent material of main part fluorenes spiral shell triphenylamine derivative of temperature and low cut-in voltage, and include the material of main part
The organic electro phosphorescent device that stability is good, luminous intensity is high, current efficiency is high.
Technical scheme：To achieve the above object, the present invention provides following technical scheme：
The fluorenes spiral shell triphenylamine derivative of the present invention, there is such as following formula（Ⅰ）Shown structure：
（Ⅰ）
Wherein, main body is substituted or unsubstituted fluorenes spiral shell triphenylamine；
A is carbazole, the miscellaneous carbazoles of α-N, the miscellaneous carbazoles of β-N, the miscellaneous carbazoles of γ-N, pyridine, diphenylamines, dimethoxy diphenylamines, two
Methyldiphenylamine or 3,6- di-t-butyl carbazoles.
Further, described fluorenes spiral shell triphenylamine derivative, main body are unsubstituted fluorenes spiral shell triphenylamine, the derivative tool
There is formula（II）Structure：
（II）.
In above-mentioned technical proposal, when A is carbazole group, the derivative has formula（I-A）Structure, be named as
SAFDCZ。
（I-A）；
In above-mentioned technical proposal, when A carbazoles miscellaneous for α-N, the derivative has formula（I-B）Structure, be named as
SAFNDCZ。
（I-B）；
In above-mentioned technical proposal, when A carbazoles miscellaneous for β-N, the derivative has formula（I-C）Structure, be named as
SAF2NDCZ
（I-C）；
In above-mentioned technical proposal, when A carbazoles miscellaneous for γ-N, the derivative has formula（I-D）Structure, be named as
SAF3NDCZ
（I-D）；
In above-mentioned technical proposal, when A is diphenylamines, the derivative has formula（I-E）Structure, be named as SAFDPh
（I-E）；
Purposes of the described fluorenes spiral shell triphenylamine derivative in organic electro phosphorescent device.
Present invention also offers a kind of organic electro phosphorescent device for including the fluorenes spiral shell triphenylamine derivative material of main part,
Including glass, the Conducting Glass layer being attached on glass, the hole injection layer being bonded with Conducting Glass layer, with hole
The hole transmission layer of implanted layer fitting, the luminescent layer being bonded with hole transmission layer, the hole blocking layer being bonded with luminescent layer, with sky
The electron transfer layer of cave barrier layer fitting, the cathode layer being bonded with electron transfer layer, described luminescent layer is by material of main part and mixes
Miscellaneous material composition, described material of main part is formula（I）The derivative of the structure, the dopant material are with cyclic metal complexes
Complex of iridium.
Preferably, described complex of iridium closes iridium for three (2- phenylpyridines) of green light（Ir(ppy)3）, acetylacetone,2,4-pentanedione
Sour two (2- phenylpyridines) iridium（Ir(ppy)2(acac)）Or double (4,6- difluorophenyl pyridinatos-N, C2') pyridine first of blue light-emitting
Acyl closes iridium（FIrpic）.
Further, Ir (ppy) 3 doping ratio is 9wt%.
Further, Ir (ppy) 2 (acac) doping ratio is 8wt%.
Further, FIrpic doping ratio is 15wt%.
Beneficial effect：The material of main part of the present invention is applied in organic electro phosphorescent device, can obtain efficient electroluminescent hair
Optical property.The organic electro phosphorescent device that the present invention is prepared using FIrpic as object, maximum luminous efficiency is up to 35.5 Kan Tela
Every ampere, maximum power efficiency up to 35.8 every watt of lumens, meanwhile, glass transition temperature of equal importance and cut-in voltage are also
Improved to great.Glass transition temperature is up to 193 DEG C, cut-in voltage minimum as little as 3 eV, with similar other devices
Property compare, be greatly improved, there is obvious advantage.
The present invention passes through the connection of the position of acridine 4,4 ' and the different characteristic electrons of modification using fluorenes spiral shell triphenylamine as construction unit
Group, fluorenes spiral shell triphenylamine derivative is obtained, effectively reduce the conjugation degree of material of main part, increased compound effective molecular weight, make
The triplet energy level and glass transition temperature of material are obtained for very big raising, while also significantly reduce it and open electricity
Pressure.The polarity of other fluorenes spiral shell triphenylamine derivative can be adjusted by the power of push/pull electron group, with conventional phosphorescence
Material of main part compares, and phosphorescent OLED device performance has obtained effective raising, can be widely applied to field of organic electroluminescence.
Brief description of the drawings
Fig. 1 is the UV-visible absorption spectrum of material of main part prepared by the embodiment of the present invention 1；
Fig. 2 is the luminescence generated by light figure of material of main part prepared by the embodiment of the present invention 1；
Fig. 3 is the EL device structure schematic diagram of the present invention, wherein 1 is substrate；2 be hole injection layer（HIL）；3
For hole transmission layer（HTL）；4 be electronic barrier layer（EBL）；5 be organic luminous layer（EML）；6 be hole blocking layer（HBL）；7
For electron transfer layer（ETL）；8 be electron injecting layer（EIL）；9 be negative electrode.
Fig. 4 is the launching light spectrogram of the electroluminescent device of the present invention.
Embodiment
Below in conjunction with the accompanying drawing in the embodiment of the present invention, detailed retouch is carried out to the technical scheme in the embodiment of the present invention
State, it is clear that described embodiment is only part of the embodiment of the present invention, rather than whole embodiments.Based in the present invention
Embodiment, the every other implementation that those of ordinary skill in the art are obtained on the premise of creative work is not made
Example, belongs to the scope of protection of the invention.
Embodiment 1
Step 1：3.24 grams of 2- bromines triphenylamines are dissolved in 80 mL tetrahydrofurans under argon gas protection, are cooled to -78
DEG C, 4.38 mL n-BuLis are slowly added in solution by constant pressure funnel, reacted 1 hour.Then by 1.8 grams of Fluorenones
It is dissolved in 40 mL tetrahydrofurans and is added drop-wise in reaction solution under argon gas protection.After low-temp reaction 1 hour, room temperature is gradually increased to,
After reaction 12 hours, 5 mL water are added in reaction, are then spin-dried for solvent by decompression.Solid is dissolved in 80 mL dichloromethanes
In alkane, organic layer is washed three times with 50 mL.Organic layer after anhydrous sodium sulfate drying with being spin-dried for.Gained solid will be spin-dried for and be dissolved in 45
In mL glacial acetic acid and 10 mL nicotinic acid, backflow is cooled to room temperature after 4 hours, then filters and is flushed three times with petroleum ether.Gained
Solid dichloromethane/petroleum ether=1:5（Volume ratio）Post is crossed, is spin-dried for obtaining 3.52 grams of fluorenes spiral shell triphenylamines, yield 85.4%.
Step 2：2.04 grams of fluorenes spiral shell triphenylamines are dissolved under the protection of argon gas in 100 mL chloroforms, when reaction solution cools down
During to 0 DEG C, 3.56 grams of N- bromo-succinimides are added portionwise in reaction solution, reacted 2 hours.Then room temperature is gradually increased to,
Reaction 12 hours.After reaction terminates, reaction dissolvent is spin-dried for, gained solid is dissolved in dichloromethane, with 50 mL washings three times.Have
Machine layer anhydrous sodium sulfate drying.It is spin-dried for solvent.The solid of gained dichloromethane/petroleum ether=1:4（Volume ratio）Post is crossed, is revolved
Do to obtain 2.3 grams of dibromo closed loop triphenylamines, yield 81.2%.
Step 3：1.11 grams of dibromo closed loop triphenylamines and 0.66 gram of carbazole are added in 50 milliliters of flasks, add catalyst
Pd2(dba)3 92 milligrams, 80 milliliters of toluene, 29 milligrams of tri-tert phosphorus tetrafluoro boric acid, 30 milligrams of sodium tert-butoxide, argon gas is protected back
Stream 12 hours, is extracted after cooling with dichloromethane, organic layer with being spin-dried for after anhydrous sodium sulfate drying, with dichloromethane/petroleum ether=
1:9（Volume ratio）Post is crossed, is spin-dried for obtaining 1.22 grams of SAFDCZ, yield 82.4%.
Embodiment 2
Step 1：It is same as the step 1 of embodiment 1.
Step 2：It is same as the step 2 of embodiment 1.
Step 3：1.11 grams of dibromo closed loop triphenylamines and the miscellaneous carbazoles of 0.68 gram of α-N are added in 50 milliliters of flasks, addition is urged
Agent Pd2(dba)3 92 milligrams, 80 milliliters of toluene, 29 milligrams of tri-tert phosphorus tetrafluoro boric acid, 30 milligrams of sodium tert-butoxide, argon gas protect
Shield backflow 12 hours, is extracted after cooling with dichloromethane, and organic layer after anhydrous sodium sulfate drying with being spin-dried for, with dichloromethane/stone
Oily ether=1:1（Volume ratio）Post is crossed, is spin-dried for obtaining 1.31 grams of SAFNDCZ, yield 88.5%.
Here is the Application Example of the compounds of this invention：
Prepare the preferred embodiment of device：
As shown in figure 3, the typical structure of OLED is：1/ anode of substrate/hole injection layer（HIL）2/ hole transmission layer
（HTL）3/ electronic barrier layer（EBL）4/ organic luminous layer（EML）5/ hole blocking layer（HBL）6/ electron transfer layer（ETL）7/ electricity
Sub- implanted layer（EIL）8/ negative electrode 9.
Substrate uses transparent conducting glass substrate, and hole injection layer can use molybdenum trioxide（MoO3）Or 2,3,6,
The azepine triphenylenes of six cyano group -1,4,5,8,9,12- of 7,10,11- six（HAT-CN）, hole transmission layer can use N, N'- hexichol
Base-N, N'- (1- naphthyls) -1,1'- biphenyl -4,4'- diamines (NPB), 4,4-N, the carbazyls of N '-two biphenyl (CBP) or 1,1 '-two
4,4 '-dimethyltrianiline thiacyclohexane (TAPC), electron transfer layer can use 1,3,5. three (N- phenyl -2- benzimidazolyl-2 radicals)
Benzene (TPBi), 4,7- diphenyl -1,10- phenanthrolenes (Bphen) or 1,3,5- tri- [(3- pyridine radicals) -3- phenyl] benzene
(TmPyPB), device architecture can be that single-shot photosphere can also be multi-luminescent layer, and it can be that single doped structure also may be used that every layer luminous
Think more doped structures.Glow color is unlimited, can be such as red, yellow, blue, green, white, and phosphorescent coloring is from double (4,6- difluorobenzenes
Yl pyridines-N, C2') pyridinecarboxylic conjunction iridium（FIrpic）, three (2- phenylpyridines) close iridium（Ir(ppy)3）, acetopyruvic acid two
(2- phenylpyridines) iridium（Ir(ppy)2(acac)）, it is double（4- tolylthiophenes simultaneously [3,2-C] pyridine-N, C2）Acetylacetone,2,4-pentanedione and iridium
（PO-01）, three (1- phenyl-isoquinolin) close iridium（Ir(piq)3）、（Acetylacetone,2,4-pentanedione）It is double（2- methyldiphenyls simultaneously [f, h] quinoxaline）
Close iridium（Ir(MDQ)2(acac)）.Negative electrode can use metal and its mixture structure, such as Mg:Al、Li:Al or electricity
Sub- implanted layer/metal-layer structure, such as LiF/Al, Liq/Al common cathode structure, wherein electron injecting layer can be alkali metal, alkali
Earth metal, the simple substance of transition metal, compound or mixture etc..Cathode material selected in the present invention is Liq/Al.
Embodiment 3
Using the compound SAFNDCZ of the present invention as OLED material of main part, FIrpic is blue phosphorescent dyes, device
Part structure is：
ITO/HAT-CN(10nm)/TAPC(45nm)/SAFDCZ:FIrpic(20nm,15vol% doping)/TmPyPB
(40nm)/Liq(2nm)/Al(120nm)。
Device fabrication process is as follows：Transparent electro-conductive glass substrate is ultrasonically treated in commercial detergent, in deionization
Rinse in water, cleaned repeatedly three times with deionized water, acetone, ethanol, be baked to moisture of going out completely under a clean environment, use
Uviol lamp and ozone processing ITO electro-conductive glass.Treated ITO electro-conductive glass is placed in vacuum chamber, it is evacuated to 3.0 ×
10-4-4.0×10-4Pa, vacuum evaporation HAT-CN is as hole injection layer on ITO electro-conductive glass（HIL）, evaporation rate is
0.25/s, coating film thickness 10nm；Vacuum evaporation TAPC is as hole transmission layer on hole injection layer（HTL）And electronics
Barrier layer（EBL）, evaporation rate is 2/s, coating film thickness 45nm；Then using the process of double source evaporation, with the present invention
Compound BCzCN is material of main part, using first organic luminous layers of the FIrpic as dyestuff（EML）, it is 2 to control evaporation rate
/ s, coating film thickness 20nm, FIrpic doping concentration are 8%.One layer of TmPyPB of vacuum evaporation makees on organic luminous layer
For the hole blocking layer of device（HBL）With electron transfer layer (ETL), evaporation rate is 2/s, coating film thickness 40nm；In electronics
Vacuum evaporation Liq and Al layer are as device cathodes, thickness 120nm in transport layer.
Embodiment 4
Using the compound SAFNDCZ of the present invention as OLED material of main part, FIrpic is blue phosphorescent dyes, device
Part structure is：ITO/CBP:MoO3(35nm,6vol% doping)/CBP(15nm)/ SAFNDCZ:Ir(ppy)2(acac)
(15nm,8vol%doping)/TmPyPB(65nm)/Liq(2nm)/Al(120nm)。
Device fabrication process is as follows：Transparent electro-conductive glass substrate is ultrasonically treated in commercial detergent, in deionization
Rinse in water, cleaned repeatedly three times with deionized water, acetone, ethanol, be baked to moisture of going out completely under a clean environment, use
Uviol lamp and ozone processing ITO electro-conductive glass.Treated ITO electro-conductive glass is placed in vacuum chamber, it is evacuated to 3.0 ×
10-4-4.0×10-4Pa, with the process of double source evaporation, vacuum evaporation CBP adulterates MoO on ITO electro-conductive glass3Layer is as empty
Cave implanted layer（HIL）And hole transmission layer（HTL）, evaporation rate is 2/s, coating film thickness 35nm, MoO3Doping concentration be
15%；Vacuum evaporation CBP is as electronic barrier layer on hole transmission layer（EBL）, evaporation rate is 2/s, and coating film thickness is
15nm；Then using the process of double source evaporation, using the compounds of this invention SAFNDCZ as material of main part, using Ir (ppy) 2
(acac) organic luminous layer as dyestuff（EML）, it is 2/s, coating film thickness 15nm, Ir (ppy) 2 to control evaporation rate
(acac) doping concentration is 8%；Hole blocking layers of the one layer of TmPyPB of vacuum evaporation as device on organic luminous layer
（HBL）And electron transfer layer（ETL）, evaporation rate is 2/s, coating film thickness 65nm；Vacuum evaporation on the electron transport layer
Liq and Al layers are as device cathodes, thickness 120nm.
Comparative example 1
Using the carbazyl benzene of 1,3- bis-（mCP）As OLED material of main part, FIrpic is blue phosphorescent dyes, device
Structure is：ITO/HAT-CN(10nm)/TAPC(45nm)/mCP:FIrpic(20nm,8vol%doping)/TmPyPB(40nm)/
Liq(2nm)/Al(120nm)。
Device fabrication process is as follows：Transparent electro-conductive glass substrate is ultrasonically treated in commercial detergent, in deionization
Rinse in water, cleaned repeatedly three times with deionized water, acetone, ethanol, be baked to moisture of going out completely under a clean environment, use
Uviol lamp and ozone processing ITO electro-conductive glass.Treated ITO electro-conductive glass is placed in vacuum chamber, it is evacuated to 3.0 ×
10-4~4.0×10-4Pa, vacuum evaporation HAT-CN is as hole injection layer on ITO electro-conductive glass（HIL）, evaporation rate is
0.25/s, coating film thickness 10nm；Vacuum evaporation TAPC is as hole transmission layer on hole injection layer（HTL）And electronics
Barrier layer（EBL）, evaporation rate is 2/s, coating film thickness 45nm；Then using the process of double source evaporation, based on mCP
Body material, using organic luminous layers of the FIrpic as dyestuff（EML）, it is 2/s, coating film thickness 20nm to control evaporation rate,
FIrpic doping concentration is 8%；Hole blocking layers of the one layer of TmPyPB of vacuum evaporation as device on organic luminous layer
（HBL）With electron transfer layer (ETL), evaporation rate is 2/s, coating film thickness 40nm；Vacuum evaporation on the electron transport layer
Liq and Al layers are as device cathodes, thickness 120nm.
The device architecture of embodiment 3-4 and comparative example 1 is shown in Table 1：
Table 1
| Device number | Device architecture |
| Embodiment 3 | ITO/HAT-CN(10nm)/TAPC(45nm)/SAFNDCZ:FIrpic(19nm,8vol%doping)/TmPyPB(40nm)/Liq(2nm)/Al(120nm) |
| Embodiment 4 | ITO/CBP:MoO3(35nm,6vol%doping)/CBP(15nm)/SAFDCZ:Ir(ppy)2(acac)(15nm,8vol%doping)/TmPyPB(65nm)/Liq (2nm)/Al(120nm) |
| Comparative example 1 | ITO/HAT-CN(10nm)/TAPC(45nm)/mCP:FIrpic(20nm,8vol%doping)/TmPyPB (40nm)/Liq(2nm)/Al(120nm) |
Current versus brightness-voltage characteristic of device is measured by the Keithley sources with corrected silicon photoelectric diode
System（Keithley 2400 Sourcemeter、Keithley 2000 Currentmeter）Complete, electroluminescent spectrum
It is to be completed by Photo research companies PR655 spectrometer measurements, all measurements in atmosphere at room temperature.
The device data of embodiment 3-4 and comparative example 1 is shown in Table 2：
Table 2
By above-mentioned 3-4 devices effect, we can rationally infer as follows：Due in electroluminescent device, the biography of energy
Defeated is to be passed to from high-energy compared with low energy, and in indigo plant, green, in red device, the energy of light-emitting guest reduces successively.Therefore, only
Want the energy of main body to be higher than blue light, and the luminous efficiency of blue light can be made to reach fine, then green and red device also can
Accordingly obtain very high efficiency.Therefore, we can rationally be inferred to green and red photophore according to above-mentioned 3-4 devices
The effect of part.
As can be seen from the above table, the device using the compounds of this invention is relative to generally using in the industry mCP, CBP main body material
The phosphorescence light emitting device of material obtains preferable result.Device two launches blue light, and maximum current efficiency high is every up to 35.5 Kan Tela
Ampere, maximum power efficiency is up to 35.8 every watt of lumens.And the glass transition temperature of all compounds is much larger than more than 180 DEG C
mCP（69℃）And CBP（62℃）, in addition, the cut-in voltage of all material is all extremely improved, and is below 4.0
EV, the wherein effect of device two is best, cut-in voltage as little as 3.0 eV, is more suitable for industrialization, can be widely applied to brightness requirement
Higher OLED large-size screen monitors are shown and OLED white-light illuminatings.
In summary, the present invention passes through the connection and modification of the position of acridine moiety 4,4 ' using fluorenes spiral shell triphenylamine as construction unit
The group of different characteristic electrons, fluorenes spiral shell triphenylamine derivative is obtained, effectively reduce the conjugation degree of material of main part, increase compound
Effective molecular weight, makes the triplet energy level of material, and glass transition temperature and cut-in voltage are obtained for very big raising.In addition
The polarity of fluorenes spiral shell triphenylamine derivative can be adjusted by push/pull electron group, compared with conventional phosphorescent light body material
Compared with phosphorescent OLED device performance has obtained effective raising, can be widely applied to field of organic electroluminescence.
It is obvious to a person skilled in the art that the invention is not restricted to the details of above-mentioned one exemplary embodiment, Er Qie
In the case of without departing substantially from spirit or essential attributes of the invention, the present invention can be realized in other specific forms.Therefore, no matter
From the point of view of which point, embodiment all should be regarded as exemplary, and be nonrestrictive, the scope of the present invention is by appended power
Profit requires rather than described above limits, it is intended that all in the implication and scope of the equivalency of claim by falling
Change is included in the present invention.
Moreover, it will be appreciated that although the present specification is described in terms of embodiments, not each embodiment is only wrapped
Containing an independent technical scheme, this narrating mode of specification is only that those skilled in the art should for clarity
Using specification as an entirety, the technical solutions in the various embodiments may also be suitably combined, forms those skilled in the art
It is appreciated that other embodiment.
Claims (1)
1. a kind of OLED, it is characterised in that be as OLED material of main part, FIrpic using compound SAFNDCZ
Blue phosphorescent dyes, device architecture are：ITO/CBP:MoO3/CBP/SAFNDCZ:Ir(ppy)2(acac)/TmPyPB/Liq/
Al；Described compound SAFNDCZ chemical structural formulas are as follows：
；
Described OLED preparation process is as follows：Transparent electro-conductive glass substrate is ultrasonically treated in commercial detergent,
Rinsed in deionized water, cleaned repeatedly three times with deionized water, acetone, ethanol, be baked to go out completely under a clean environment
Moisture, ITO electro-conductive glass is handled with uviol lamp and ozone；Treated ITO electro-conductive glass is placed in vacuum chamber, is evacuated to
3.0×10-4-4.0×10-4Pa, with the process of double source evaporation, vacuum evaporation CBP adulterates MoO on ITO electro-conductive glass3Layer
As hole injection layer and hole transmission layer, evaporation rate is 2/s, coating film thickness 35nm, MoO3Doping concentration be 15%；
For vacuum evaporation CBP as electronic barrier layer, evaporation rate is 2/s, coating film thickness 15nm on hole transmission layer；Then
The process being deposited using double source, using compound SAFNDCZ as material of main part, using Ir (ppy) 2 (acac) as dyestuff
Organic luminous layer, it is 2/s to control evaporation rate, and coating film thickness 15nm, Ir (ppy) 2 (acac) doping concentration is 8%；
Hole blocking layers and electron transfer layer of the one layer of TmPyPB of vacuum evaporation as device, evaporation rate 2 on organic luminous layer
/ s, coating film thickness 65nm；Vacuum evaporation Liq and Al layers are as device cathodes, thickness 120nm on the electron transport layer.
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| CN108070073B (en) * | 2016-11-10 | 2020-07-07 | 中国科学院长春应用化学研究所 | Polyspirofluorene and organic electroluminescent device |
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| KR101989952B1 (en) * | 2017-06-16 | 2019-06-17 | 경상대학교산학협력단 | Novel acridine derivatives and organic electroluminescent devices containing them |
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