CN103887447A - Organic electroluminescent device - Google Patents
Organic electroluminescent device Download PDFInfo
- Publication number
- CN103887447A CN103887447A CN201410128310.1A CN201410128310A CN103887447A CN 103887447 A CN103887447 A CN 103887447A CN 201410128310 A CN201410128310 A CN 201410128310A CN 103887447 A CN103887447 A CN 103887447A
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- electroluminescence device
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- 238000002347 injection Methods 0.000 claims abstract description 11
- 239000007924 injection Substances 0.000 claims abstract description 11
- 230000004888 barrier function Effects 0.000 claims abstract description 5
- -1 D-atom Chemical class 0.000 claims description 45
- 238000005401 electroluminescence Methods 0.000 claims description 34
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 21
- 125000001624 naphthyl group Chemical group 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 16
- HHRFWSALGNYPHA-UHFFFAOYSA-N [N].C1CNCCN1 Chemical compound [N].C1CNCCN1 HHRFWSALGNYPHA-UHFFFAOYSA-N 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 12
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 6
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- 239000001257 hydrogen Substances 0.000 claims description 6
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- 238000006579 Tsuji-Trost allylation reaction Methods 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
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- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical class C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 2
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- 125000001725 pyrenyl group Chemical group 0.000 claims description 2
- 239000000463 material Substances 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
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- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
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- 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
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- 238000005481 NMR spectroscopy Methods 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
- 229910052783 alkali metal Inorganic materials 0.000 description 4
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- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
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- 229910052751 metal Inorganic materials 0.000 description 4
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- 238000000034 method Methods 0.000 description 4
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- WREOTYWODABZMH-DTZQCDIJSA-N [[(2r,3s,4r,5r)-3,4-dihydroxy-5-[2-oxo-4-(2-phenylethoxyamino)pyrimidin-1-yl]oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]1N(C=C\1)C(=O)NC/1=N\OCCC1=CC=CC=C1 WREOTYWODABZMH-DTZQCDIJSA-N 0.000 description 3
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- 150000004820 halides Chemical class 0.000 description 3
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
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- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000009832 plasma treatment Methods 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
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- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
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- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- AIACLXROWHONEE-UHFFFAOYSA-N 2,3-dimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=C(C)C(=O)C=CC1=O AIACLXROWHONEE-UHFFFAOYSA-N 0.000 description 1
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 1
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- IIRVBNFPODABQL-UHFFFAOYSA-N N,N-diphenylaniline ethene Chemical group C1(=CC=CC=C1)N(C1=CC=CC=C1)C1=CC=CC=C1.C=C IIRVBNFPODABQL-UHFFFAOYSA-N 0.000 description 1
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
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- JCWIWBWXCVGEAN-UHFFFAOYSA-L cyclopentyl(diphenyl)phosphane;dichloropalladium;iron Chemical compound [Fe].Cl[Pd]Cl.[CH]1[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1.[CH]1[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1 JCWIWBWXCVGEAN-UHFFFAOYSA-L 0.000 description 1
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- 125000001153 fluoro group Chemical group F* 0.000 description 1
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- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- IDBFBDSKYCUNPW-UHFFFAOYSA-N lithium nitride Chemical compound [Li]N([Li])[Li] IDBFBDSKYCUNPW-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
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- 150000002894 organic compounds Chemical class 0.000 description 1
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- 150000002964 pentacenes Chemical class 0.000 description 1
- 150000002988 phenazines Chemical class 0.000 description 1
- MQKPEUAOJLJUMD-UHFFFAOYSA-N phenol;piperazine Chemical class C1C[NH2+]CCN1.[O-]C1=CC=CC=C1 MQKPEUAOJLJUMD-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
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- 238000002360 preparation method Methods 0.000 description 1
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- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
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
-
- 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]
- H10K50/14—Carrier transporting layers
-
- 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]
- H10K50/17—Carrier injection 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides an organic electroluminescent device which comprises an anode, a cathode and an organic layer. The organic layer comprises one or more layers of a hole injection layer, a hole transmission layer, a luminescent layer, a barrier layer, an electro injection layer and an electron transmission layer. At least one layer in the organic layer comprises a compound with the following structural formula (I) (please see the structural formula (I) in the specification).
Description
Technical field
The present invention relates to organic electroluminescent field, relate to specifically a kind of organic electroluminescence device.
Background technology
Organic electroluminescence device (OLEDs) for being steamed and crossed the device that deposition one deck organic material is prepared from by spin coating or vacuum between two metal electrodes, three layers of classical organic electroluminescence device comprise hole transmission layer, luminescent layer and electron transfer layer.The hole being produced by anode is followed the electronics being produced by negative electrode to be combined in luminescent layer through electron transfer layer and is formed exciton through hole transmission layer, then luminous.Organic electroluminescence device can regulate the light of the various needs of transmitting as required by changing the material of luminescent layer.
Organic electroluminescence device is as a kind of novel Display Technique, have that self-luminous, wide visual angle, low energy consumption, efficiency are high, thin, rich color, fast response time, Applicable temperature scope are wide, low driving voltage, can make flexible and the transparent particular advantages such as display floater and environmental friendliness, can be applied in flat-panel monitor and a new generation's illumination above, also can be used as the backlight of LCD.
Since invention at the bottom of the eighties in 20th century, organic electroluminescence device is industrially application to some extent, and such as the screen such as camera and mobile phone, but current OLED device is because efficiency is low, the factors such as useful life is short restrict it and apply widely, particularly large screen display.And restrict the performance that one of them key factor is exactly the electroluminescent organic material in organic electroluminescence device.Because OLED device is applying voltage-operated time, can produce Joule heat in addition, make organic material that crystallization easily occur, affect life-span and the efficiency of device, therefore, also need to develop the electroluminescent organic material of stability and high efficiency.
In OLED material, because the speed of most electroluminescent organic material transporting holes is faster than the speed of transmission electronic, easily cause electronics and the number of cavities imbalance of luminescent layer, the efficiency of device is just lower like this.Three (oxine) aluminium (Alq
3) since invention, be extensively studied, but still very low as its electron mobility of electron transport material, and the intrinsic characteristic that self can degrade, taking in the device of electron transfer layer, there will be the situation of voltage drop, simultaneously, due to lower electron mobility, make a large amount of holes enter into Alq
3in layer, excessive hole is with non-luminous form emittance, and when as electron transport material, due to the characteristic of its green light, in application, is restricted.Therefore, development stability and have the electron transport material of larger electron mobility, has great value to being widely used of organic electroluminescence device.
Summary of the invention
First the present invention provides a kind of organic electroluminescent compounds, and it is the compound with following structural formula I:
Wherein, R
1-R
8be respectively replacement or the unsubstituted alkynes alkyl of the replacement of the replacement of the replacement of hydrogen, D-atom, halogen, cyano group, nitro, C1-C8 alkyl, C1-C8 alkoxyl, C6-C30 or unsubstituted aryl, C3-C30 or unsubstituted heteroaryl, C2-C8 or unsubstituted allylic alkylation, C2-C8 independently;
Ar
1, Ar
2and Ar
3be respectively replacement or the unsubstituted heteroaryl of the replacement of C1-C8 alkyl, C6-C60 or unsubstituted aryl, C3-C60 independently;
L
1and L
2be replacement or the unsubstituted aryl of sky, singly-bound, C6-C30 independently respectively.
Wherein preferred mode is:
R
1-R
8be respectively the replacement of the replacement of hydrogen, halogen, cyano group, nitro, C1-C8 alkyl, C1-C8 alkoxyl, C2-C8 or unsubstituted allylic alkylation, C2-C8 or unsubstituted alkynes alkyl, phenyl, naphthyl, pyridine radicals, pyrimidine radicals, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinoline independently;
Ar
1, Ar
2and Ar
3be respectively by phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylene base, the fluoranthene base of C1-C4 alkyl or the replacement of C6-C30 aryl independently; Or Ar
1, Ar
2and Ar
3be (9 independently respectively, 9-dialkyl group) fluorenyl, (9,9-bis-replaces or unsubstituted aryl) fluorenyl, 9,9-is Spirofluorene-based, replacement or unsubstituted dibenzothiophenes base, replacement or unsubstituted dibenzofuran group, pyridine radicals, pyrimidine radicals, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinoline;
L
1and L
2be respectively sky, singly-bound, phenyl, the phenyl being replaced by C1-C4 alkyl, naphthyl, the naphthyl that replaced by C1-C4 alkyl independently;
Wherein above-mentioned phenyl, naphthyl, pyridine radicals, pyrimidine radicals, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinoline can further be replaced by the alkyl of C1-C4;
Further preferred mode is:
R
1-R
8independently be selected from respectively hydrogen, methoxyl group, fluorine, methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl, phenyl, naphthyl, pyridine radicals, pyrimidine radicals, triazol radical, three nitrogen piperazine bases, quinolyl;
L
1and L
2respectively independently selected from sky, singly-bound, phenyl, naphthyl;
Ar
1, Ar
2and Ar
3independently be selected from respectively methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl, phenyl, naphthyl, pyridine radicals, pyrimidine radicals, triazol radical, three nitrogen piperazine bases, quinolyl, replacement or unsubstituted following aryl:
Wherein above-mentioned phenyl, naphthyl, pyridine radicals, pyrimidine radicals, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinoline can further be replaced by the alkyl of C1-C4.
Further preferred, the compound that organic electroluminescent compounds of the present invention is following structural 1-36.
Organic electroluminescent compounds of the present invention can prepare by Suzuki coupling and Buchwald-Hartwig reaction.
Organic electroluminescent compounds of the present invention can be applied in organic electroluminescence device, organic solar batteries, OTFT or organophotoreceptorswith field.
The present invention also provides a kind of organic electroluminescence device, this device comprises anode, negative electrode and organic layer, organic layer comprises one or more layers in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer and electron transfer layer, has at least one deck to contain just like organic electroluminescent compounds structural formula (I) Suo Shu in wherein said organic layer:
Structural formula I
Wherein R
1-R
8, Ar
1-Ar
3, and L
1-L
2definition as previously mentioned.
Wherein organic layer is luminescent layer;
Or organic layer is luminescent layer and hole injection layer;
Or organic layer is luminescent layer and hole transmission layer;
Or organic layer is luminescent layer and electron transfer layer;
Or organic layer is luminescent layer, hole injection layer, hole transmission layer and electron transfer layer;
Or organic layer is luminescent layer, hole injection layer, hole transmission layer, electron transfer layer and electron injecting layer;
Or organic layer is luminescent layer, hole injection layer, hole transmission layer, electron transfer layer, electron injecting layer and barrier layer;
Or organic layer is luminescent layer, hole transmission layer, electron transfer layer, electron injecting layer and barrier layer;
Or organic layer is luminescent layer, hole transmission layer, electron injecting layer and barrier layer;
Wherein the layer at the organic electroluminescent compounds place as described in structural formula (I) is luminescent layer, electron transfer layer or hole injection layer;
Wherein the described organic electroluminescent compounds of structural formula (I) is the compound of structural formula 1-36;
Organic electroluminescent compounds as described in structural formula I can use separately, also can use with other compound; Organic electroluminescent compounds as described in structural formula I can use separately a kind of compound wherein, also can use two or more the compound in structural formula I simultaneously.
Organic electroluminescence device of the present invention, further preferred mode is, this organic electroluminescence device comprises anode, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, wherein in electron transfer layer, contains the compound of structural formula (I); Further preferred, the compound that the compound in electron transfer layer is structural formula 1-36.
Structural formula I compound during as luminescent layer, can be used as non-impurity-doped luminescent layer or doping luminescent layer.
Described doping luminescent layer comprises material of main part and guest materials, and structural formula (I) compound is during as material of main part, and its concentration is the 20-99.9% of whole luminescent layer weight, preferably 80-99%, more preferably 90-99%.Structural formula (I) compound is during as guest materials, and its concentration is 0.01-80% of this luminescent layer weight, preferably 1-20%, more preferably 1-10%.
Can use two compounds of structural formula I to make respectively material of main part and guest materials simultaneously.
The gross thickness of organic electroluminescence device organic layer of the present invention is 1-1000nm, preferably 50-500nm.
The hole transmission layer of organic electroluminescence device of the present invention and hole injection layer, material requested has good hole transport performance, can effectively hole be transferred to luminescent layer from anode.Have the described compound of structural formula (I) except above-mentioned, can also comprise other little molecule and macromolecular organic compounds, include but not limited to triaromatic amine compound, benzidine compound, compound of fluorene class, phthalocyanine-like compound, the assorted triphen (hexanitrilehexaazatriphenylene), 2 of six cyano group six, 3,5,6-tetrafluoro-7,7 ', 8,8 '-tetra-cyanogen dimethyl 1,4-benzoquinone (F4-TCNQ), Polyvinyl carbazole, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of organic electroluminescence device of the present invention, has the good characteristics of luminescence, can regulate as required the scope of visible ray.Except containing phenol piperazine compounds of the present invention, can also contain following compound, include, but are not limited to naphthalene compounds, pyrene compound, compound of fluorene class, luxuriant and rich with fragrance compounds, bend compounds, fluoranthene compounds, anthracene compounds, pentacene compounds, perylene compounds, two aromatic ethylene compounds, triphenylamine ethylene compounds, aminated compounds, carbazole compound, benzimidazoles compound, furfuran compound, metal organic fluorescence complex compound, the organic phosphorescence complex compound of metal is (as Ir, Pt, Os, Cu), polyvinylcarbazole, poly-organosilicon compound, the organic polymer luminescent materials such as polythiophene, they can use separately, also can use by multiple mixture.The thickness of luminescent layer is preferably 10-50nm.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires to have good electronic transmission performance, can, effectively during electronics is from cathode transport to luminescent layer, have very large electron mobility.Can select following compound, but be not limited to this, oxa-oxazole, thiazole compound, triazole compound, three nitrogen piperazine compounds, triazine compounds, quinoline compounds, phenazine compounds, siliceous heterocycle compound, quinolines, ferrosin compounds, metallo-chelate (as Alq3), fluorine substituted benzene compound.
The electron injecting layer of organic electroluminescence device of the present invention, can effectively electronics be injected into organic layer from negative electrode, mainly be selected from alkali metal or alkali-metal compound, or be selected from compound or the alkali metal complex of alkaline-earth metal or alkaline-earth metal, can select following compound, but be not limited to this, oxide or halide, the oxide of rare earth metal or the organic complex of halide, alkali metal or alkaline-earth metal of the oxide of alkali metal, alkaline-earth metal, rare earth metal, alkali gold brush or halide, alkaline-earth metal; Be preferably lithium, lithium fluoride, lithia, lithium nitride, oxine lithium, caesium, cesium carbonate, oxine caesium, calcium, calcirm-fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate, magnesium oxide, these compounds can use separately also and can use by mixture, also can be used in conjunction with other electroluminescent organic materials.
Every one deck of organic layer in organic electroluminescence device of the present invention, can steam the modes such as the method for crossing, molecular beam vapour deposition method, the dip coating that is dissolved in solvent, spin-coating method, excellent painting method or inkjet printing and prepare by vacuum.Can use vapour deposition method or sputtering method to be prepared for metal motor.
Device experimental shows, the organic electroluminescent compounds of the present invention as described in structural formula (I), has better thermal stability, high-luminous-efficiency, high luminance purity.The organic electroluminescence device that adopts this organic electroluminescent compounds to make have advantages of the good and colorimetric purity excellence of electroluminescent efficiency and the life-span long.
Brief description of the drawings
Fig. 1 is a kind of organic electroluminescence device structural representation of the present invention
Wherein, 110 are represented as glass substrate, and 120 are represented as anode, and 130 are represented as hole transmission layer, and 140 are represented as luminescent layer, and 150 are represented as electron transfer layer, and 160 are represented as electron injecting layer, and 170 are represented as negative electrode.
Fig. 2 is that embodiment 2 is at 100mA/em
2current density under emission spectrum.
Embodiment
In order more to describe the present invention in detail, especially exemplified by following example, but be not limited to this.
Embodiment 1
Synthesizing of compound 15
Intermediate 15-2's is synthetic
In flask, add compound 15-1 (2g, 5.1mmol), connection boric acid is frequently received alcohol ester (1.5g, 6.18mmol), potassium acetate (15.4mmol), Pd (dppf)
2cl
2(100mg), the DMF of 40ml, is heated to 90 DEG C of reactions 12 hours under nitrogen protection; cooling, be poured into water, with dichloromethane extraction, with anhydrous sodium sulfate drying; concentrated, crude product is purified and is obtained 1.5g white solid with silicagel column, and productive rate is 68%.
1H?NMR(400MHz，CDCl
3，δ)：8.75-8.80(m，6H)，8.00-8.02(d，J=8Hz，2H)，7.57-7.63(m，6H)，1.40(s，12H)。
Intermediate 15-3 and 15-4's is synthetic
In flask, add N-phenyl-1, the NMP (1-METHYLPYRROLIDONE) of 2-phenylenediamine (9.2g, 50mmol) and 80ml, then add stirring reaction under 4-bromo-benzoyl chloride (10.9g, 50mmol) room temperature to spend the night.React, reactant liquor is poured into water, has a large amount of solids to separate out, filter, THF for filter cake (oxolane) and recrystallizing methanol, the white solid that obtains (intermediate 15-3) adds 100ml acetic acid to add hot reflux 12 hours, has reacted removal of solvent under reduced pressure, add 50ml methyl alcohol, filter, obtain 12g white solid (intermediate 15-4), productive rate is 69%.Wherein the nuclear-magnetism of 15-4 is:
1H?NMR(400MHz，DMSO，δ)：7.78-7.81(d，J=7.6Hz，1H)，7.54-7.60(m，5H)，7.43-7.46(m，4H)，7.26-7.34(m，2H)，7.17-7.19(d，J=7.2Hz，1H).
Intermediate 15-5's is synthetic
Under nitrogen protection, in the there-necked flask that the THF that intermediate 15-4 (10.6g, 29mmol) and 100ml were dried adds, but to-78 DEG C.Under agitation slowly inject subsequently the n-BuLi hexane solution (20mL of 2.5M with syringe; 50mmol); and then add triisopropyl borate ester (8.1g; 43mmol); at this temperature, continue to stir 1 hour; then slowly rise to room temperature, under nitrogen protection, stir and spend the night.React, reactant liquor has been poured in the dilute hydrochloric acid solution of 2N, and be extracted with ethyl acetate three times, merged organic phase, used successively salt solution and washing, then use anhydrous sodium sulfate drying.Except desolventizing, crude product obtains 8.3g white solid with ethyl acetate and n-hexane recrystallization, and productive rate is 74%.
1HNMR(400MHz，DMSOδ)：8.14(s，2H)，7.34-7.82(m，3H)，7.43-7.50(m，7H)，7.20-7.35(m，3H)。
Intermediate 15-6's is synthetic
In flask, add 9-bromine anthracene (0.77g, 3mmol), intermediate 15-5 (0.92g, 3mmol), the 2M K of the THF of 10ml and 10ml
2cO
3the aqueous solution; under nitrogen protection, add 50mg tetra-(triphenyl phosphorus) palladium, then heat 12 hours; react; cooling, use dichloromethane extraction three times, organic layer anhydrous sodium sulfate drying; organic solvent is removed in decompression; crude product ethyl alcohol recrystallization, obtains 0.94g yellow solid, and productive rate is 70%.
1H?NMR(400MHz，CDCl
3，δ)：8.49(s，1H)，8.03-8.05(d，J=8.4Hz，2H)，7.94-7.96(d，J=8.0Hz，1H)，7.78-7.80(d，J=8.4Hz，2H)，7.57-7.63(m，4H)，7.44-7.54(m，5H)，7.31—7.40(m，7H).
Intermediate 15-7's is synthetic
In flask, add intermediate 15-6 (0.95g, 2.13mmol), NBS (N-bromo-succinimide) (0.4g, 2.13mmol) and 10ml chloroform.Under nitrogen protection, be heated to 50 DEG C of reactions 12 hours.Reacted, removed chloroform, crude product obtains 0.75g yellow solid with acetone and methyl alcohol mixed solvent recrystallization, and productive rate is 68%.
1H?NMR(400MHz，CDCl
3，δ)：8.60-8.62(d，J=8.4Hz，2H)，7.94-7.96(d，J=8.0Hz，1H)，7.79-7.81(d，J=8.0Hz，2H)，7.54-7.62(m，7H)，7.47-7.48(d，J=8.4Hz，2H)，7.33-7.41(m，5H)，7.32(m，2H).
Synthesizing of compound 15
In single port flask; add intermediate 15-2 (0.3g; 0.68mmol); intermediate 15-7 (0.3g, 0.57mmol), the 2M wet chemical of the oxolane of 10ml and 10ml; under nitrogen protection; add four (triphenyl phosphorus) palladiums (10mg, 0.0075mmol), then add hot reflux 12 hours; react; cooling, use dichloromethane extraction three times, organic layer anhydrous sodium sulfate drying; organic solvent is removed in rotation; crude product carries out column chromatography purification, obtains 0.31g yellow solid, and productive rate is 72%.
ESI, m/z:[M+H]
+calcd for C
54h
36n
5, theoretical value is: 754.30; Measured value: 754.29.
Embodiment 2
The preparation of organic electroluminescence device
Use the compound of embodiment 1 to prepare OLED
First, by electrically conducting transparent ito glass substrate 110 (above with anode 120) (China Nanbo Group Co) warp successively: deionized water, ethanol, acetone and deionized water are cleaned, then use oxygen plasma treatment 30 seconds.
Then, steam and cross NPB, form the thick hole transmission layer 130 of 60nm.
Then, on hole transmission layer, steam and cross the compd A lq that 30nm is thick
3as luminescent layer 140.
Then, on luminescent layer, steam and cross compound 15 that 20nm is thick as electron transfer layer 150.
Finally, steam that to cross 1nm LiF be that electron injecting layer 160 and 100nmAl are as device cathodes 170.
Prepared device records at 50mA/cm with Photo Research PR650 spectrometer
2current density under efficiency be 2.13cd/A, 100mA/cm
2current density under efficiency be 2.54cd/A, Fig. 2 represents that the organic electroluminescence device of the present embodiment is at 100mA/cm
2current density under emission spectrum, be green spectral.
Comparative example 1
First, by electrically conducting transparent ito glass substrate 110 (above with anode 120) (China Nanbo Group Co) warp successively: deionized water, ethanol, acetone and deionized water are cleaned, then use oxygen plasma treatment 30 seconds.
Then, steam and cross NPB, form the thick hole transmission layer 130 of 60nm.
Then, on hole transmission layer, steam and cross the Alq that 30nm is thick
3as luminescent layer 140.
Then, on luminescent layer, steam and cross the Alq that 20nm is thick
3as electron transfer layer 150.
Finally, steam that to cross 1nm LiF be that electron injecting layer 160 and 100nmAl are as device cathodes 170.
Prepared device records at 50mA/cm with Photo Research PR650 spectrometer
2current density under efficiency be 0.55cd/A, 50mA/cm
2current density under efficiency be 0.94cd/A, transmitting green light
Under identical condition, apply the efficiency of organic electroluminescence device prepared by organic electroluminescent compounds of the present invention higher than comparative example.As mentioned above, compound of the present invention has high stability, and organic electroluminescence device prepared by the present invention has high efficiency and optical purity.
Structural formula described in device
Claims (9)
1. an organic electroluminescence device, it comprises anode, negative electrode and organic layer, organic layer comprises one or more layers in hole injection layer, hole transmission layer, luminescent layer, barrier layer, electron injecting layer and electron transfer layer, it is characterized in that in organic layer that one deck at least includes the compound of following structural formula (I)
Wherein, R
1-R
8be respectively replacement or the unsubstituted alkynes alkyl of the replacement of the replacement of the replacement of hydrogen, D-atom, halogen, cyano group, nitro, C1-C8 alkyl, C1-C8 alkoxyl, C6-C30 or unsubstituted aryl, C3-C30 or unsubstituted heteroaryl, C2-C8 or unsubstituted allylic alkylation, C2-C8 independently;
Ar
1, Ar
2and Ar
3be respectively replacement or the unsubstituted heteroaryl of the replacement of C1-C8 alkyl, C6-C60 or unsubstituted aryl, C3-C60 independently;
L
1and L
2be replacement or the unsubstituted aryl of sky, singly-bound, C6-C30 independently respectively.
2. organic electroluminescence device according to claim 1, is characterized in that
Wherein, R
1-R
8be respectively the replacement of the replacement of hydrogen, halogen, cyano group, nitro, C1-C8 alkyl, C1-C8 alkoxyl, C2-C8 or unsubstituted allylic alkylation, C2-C8 or unsubstituted alkynes alkyl, phenyl, naphthyl, pyridine radicals, pyrimidine radicals, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinoline independently;
Ar
1, Ar
2and Ar
3be respectively by phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylene base, the fluoranthene base of C1-C4 alkyl or the replacement of C6-C30 aryl independently; Or Ar
1, Ar
2and Ar
3be (9 independently respectively, 9-dialkyl group) fluorenyl, (9,9-bis-replaces or unsubstituted aryl) fluorenyl, 9,9-is Spirofluorene-based, replacement or unsubstituted dibenzothiophenes base, replacement or unsubstituted dibenzofuran group, pyridine radicals, pyrimidine radicals, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinoline;
L
1and L
2be respectively sky, singly-bound, phenyl, the phenyl being replaced by C1-C4 alkyl, naphthyl, the naphthyl that replaced by C1-C4 alkyl independently;
Wherein phenyl, naphthyl, pyridine radicals, pyrimidine radicals, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinoline can further be replaced by the alkyl of C1-C4.
3. organic electroluminescence device according to claim 1, is characterized in that wherein
R
1-R
8independently be selected from respectively hydrogen, methoxyl group, fluorine, methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl, phenyl, naphthyl, pyridine radicals, pyrimidine radicals, triazol radical, three nitrogen piperazine bases, quinolyl;
L
1and L
2respectively independently selected from sky, singly-bound, phenyl, naphthyl;
Ar
1, Ar
2and Ar
3independently be selected from respectively methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl, phenyl, naphthyl, pyridine radicals, pyrimidine radicals, triazol radical, three nitrogen piperazine bases, quinolyl, replacement or unsubstituted following aryl:
Wherein phenyl, naphthyl, pyridine radicals, pyrimidine radicals, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinoline can further be replaced by the alkyl of C1-C4.
4. organic electroluminescence device according to claim 1, the compound that it is characterized in that structural formula (I) is the compound of following structural 1-36,
5. organic electroluminescence device according to claim 1, the layer that it is characterized in that the compound place as described in structural formula (I) is luminescent layer, electron transfer layer or hole injection layer.
6. organic electroluminescence device according to claim 1, is characterized in that the compound as described in structural formula (I) can use separately, also can use with other compound.
7. organic electroluminescence device according to claim 1, it is characterized in that the compound as described in structural formula (I) can use separately a kind of compound wherein, also can use two or more the compound in structural formula (I) simultaneously.
8. organic electroluminescence device according to claim 1, it comprises anode, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, it is characterized in that the compound that contains structural formula (I) in electron transfer layer.
9. organic electroluminescence device according to claim 8, is characterized in that the compound in electron transfer layer is the compound of structural formula 1-36.
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| CN109651276A (en) * | 2018-12-31 | 2019-04-19 | 瑞声科技（南京）有限公司 | It is a kind of based on triazine-anthracene structure heterocyclic compound and its application |
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