CN106749401A - A kind of carbazole analog derivative and its preparation method and application - Google Patents
A kind of carbazole analog derivative and its preparation method and application Download PDFInfo
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- CN106749401A CN106749401A CN201610985264.6A CN201610985264A CN106749401A CN 106749401 A CN106749401 A CN 106749401A CN 201610985264 A CN201610985264 A CN 201610985264A CN 106749401 A CN106749401 A CN 106749401A
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- unsubstituted
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- analog derivative
- carbazole analog
- carbazole
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- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title abstract 4
- 238000005401 electroluminescence Methods 0.000 claims abstract description 17
- 150000001716 carbazoles Chemical class 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
- 239000005416 organic matter Substances 0.000 claims description 9
- 230000005540 biological transmission Effects 0.000 claims description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 3
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000001725 pyrenyl group Chemical group 0.000 claims description 3
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 2
- 239000000463 material Substances 0.000 abstract description 13
- 239000002994 raw material Substances 0.000 abstract description 4
- 238000005516 engineering process Methods 0.000 abstract description 3
- 230000005693 optoelectronics Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 37
- 239000000047 product Substances 0.000 description 21
- -1 colored filter Substances 0.000 description 19
- 239000000470 constituent Substances 0.000 description 16
- 238000001819 mass spectrum Methods 0.000 description 16
- 238000005259 measurement Methods 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 15
- 235000010290 biphenyl Nutrition 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- 239000000758 substrate Substances 0.000 description 8
- 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 8
- 239000002585 base Substances 0.000 description 7
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 102100031383 Fibulin-7 Human genes 0.000 description 4
- 101000846874 Homo sapiens Fibulin-7 Proteins 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 0 *c(c(C1CC1)c(*)c([U])c1*)c1N(C1c2c11)c3ccccc3-c1ccc2-[n](c1c2cccc1)c1c2*(cccc2)c2c(P(C2C=CC=CC2)c2ccccc2)c1 Chemical compound *c(c(C1CC1)c(*)c([U])c1*)c1N(C1c2c11)c3ccccc3-c1ccc2-[n](c1c2cccc1)c1c2*(cccc2)c2c(P(C2C=CC=CC2)c2ccccc2)c1 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000027756 respiratory electron transport chain Effects 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- AELBZZMQJAJEJW-UHFFFAOYSA-N 1-bromo-9-phenylcarbazole Chemical class BrC1=CC=CC(C2=CC=CC=C22)=C1N2C1=CC=CC=C1 AELBZZMQJAJEJW-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 2
- RHPLIXXDJSEYDC-UHFFFAOYSA-N 1-bromo-1h-indene Chemical class C1=CC=C2C(Br)C=CC2=C1 RHPLIXXDJSEYDC-UHFFFAOYSA-N 0.000 description 1
- VCDOOGZTWDOHEB-UHFFFAOYSA-N 1-bromo-9h-carbazole Chemical compound N1C2=CC=CC=C2C2=C1C(Br)=CC=C2 VCDOOGZTWDOHEB-UHFFFAOYSA-N 0.000 description 1
- SODQFLRLAOALCF-UHFFFAOYSA-N 1lambda3-bromacyclohexa-1,3,5-triene Chemical compound Br1=CC=CC=C1 SODQFLRLAOALCF-UHFFFAOYSA-N 0.000 description 1
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 description 1
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 1
- SGNQVBCFSRWNCJ-UHFFFAOYSA-N C(C1)C=Cc2c1c(C1C=CC=CC1C(P(c1ccccc1)c1ccccc1)=C1)c1[n]2-c(cc1)ccc1-c(cc1C2C3=CC=CC2)ccc1N3c1ccccc1 Chemical compound C(C1)C=Cc2c1c(C1C=CC=CC1C(P(c1ccccc1)c1ccccc1)=C1)c1[n]2-c(cc1)ccc1-c(cc1C2C3=CC=CC2)ccc1N3c1ccccc1 SGNQVBCFSRWNCJ-UHFFFAOYSA-N 0.000 description 1
- ZIQVMKGEAQZZES-UHFFFAOYSA-N C(C=C1)c2c1ccc(-[n]1c3cc(P(C4C=CC=CC4)c4ccccc4)c(cccc4)c4c3c3c1cccc3)c2 Chemical compound C(C=C1)c2c1ccc(-[n]1c3cc(P(C4C=CC=CC4)c4ccccc4)c(cccc4)c4c3c3c1cccc3)c2 ZIQVMKGEAQZZES-UHFFFAOYSA-N 0.000 description 1
- LHNHUIDRZCWVBH-UHFFFAOYSA-N C1C=CC=CC1P(c1ccccc1)c1c(cccc2)c2c(c(cccc2)c2[n]2-c(cc3)cc4c3c(cccc3)c3[n]4-c3ccccc3)c2c1 Chemical compound C1C=CC=CC1P(c1ccccc1)c1c(cccc2)c2c(c(cccc2)c2[n]2-c(cc3)cc4c3c(cccc3)c3[n]4-c3ccccc3)c2c1 LHNHUIDRZCWVBH-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- YKHYKIQZQWCOGP-UHFFFAOYSA-N c(cc1)ccc1P(c1ccccc1)c1cc([n](c2c3cccc2)-c(cc2)ccc2-[n]2c4ccccc4c4c2cccc4)c3c2c1cccc2 Chemical compound c(cc1)ccc1P(c1ccccc1)c1cc([n](c2c3cccc2)-c(cc2)ccc2-[n]2c4ccccc4c4c2cccc4)c3c2c1cccc2 YKHYKIQZQWCOGP-UHFFFAOYSA-N 0.000 description 1
- UNFLWCNFOSRTPK-UHFFFAOYSA-N c(cc1)ccc1P(c1ccccc1)c1cc([n](c2c3cccc2)-c2c(ccc4cccc(cc5)c44)c4c5cc2)c3c2c1cccc2 Chemical compound c(cc1)ccc1P(c1ccccc1)c1cc([n](c2c3cccc2)-c2c(ccc4cccc(cc5)c44)c4c5cc2)c3c2c1cccc2 UNFLWCNFOSRTPK-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
-
- 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
- H10K50/15—Hole transporting layers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present invention provides a kind of carbazole analog derivative and its preparation method and application, is related to organic optoelectronic materials technology.Carbazole analog derivative obtained by the present invention can be used to prepare organic electroluminescence device, especially as the hole mobile material in organic electroluminescence device, can effectively improve the luminous efficiency and long lifespan of OLED.The present invention also provides a kind of preparation method of carbazole analog derivative, and the preparation method is simple, raw material is easy to get.
Description
Technical field
The present invention relates to organic photoelectrical material technical field, and in particular to a kind of carbazole analog derivative and preparation method thereof and
Using.
Background technology
At present, display screen is based on TFT (Thin Film Transistor, TFT)-LCD, due to
It is the display of non-spontaneous light, it is therefore necessary to passes through backlight throw light, and sequentially penetrates the polarisation in TFT-LCD panels
The correlation spare part such as plate, glass substrate, liquid crystal layer, colored filter, glass substrate, Polarizer, finally enter the eyes of people into
Picture, can be only achieved the function of display.Just because of above-mentioned complicated display process, its display screen occurs in actual application
Reaction rate is slow, power consumption, narrow viewing angle the shortcomings of, be not enough to turn into perfect display screen.
Organic electroluminescence device (Organic Light-emitting Device, OLED) shows as flat board of new generation
Show that utensil there are following features：(1) design aspect：Simple structure, high yield rate, low cost；Background light source and optical filter are not needed,
Product that is ultra-thin, lightweight, being easy to carry about with one thus can be produced.(2) display aspect：Actively luminous, angular field of view is big；Response
Speed is fast, image stabilization；Brightness is high, and glow color is from infrared to ultraviolet, rich color, high resolution.(3) condition of work：Drive
Dynamic voltage is low, energy consumption is low, can match with solar cell, integrated circuit etc..(4) wide adaptability：Can be real using glass substrate
Existing large-area flat-plate shows；Substrate such as is done with flexible material, folding display can be made.(5) due to OLED be it is all solid state,
Antivacuum device, swings, the characteristic such as low temperature resistant (- 40 DEG C) with antidetonation.
In general, OLED can be divided into two kinds by luminescent material：Small molecule OLED and macromolecule OLED are (alternatively referred to as
PLED).Small molecule OLED is different with the preparation technology that the difference of macromolecule OLED is mainly manifested in device：Small molecule devices are main
Using vacuum thermal evaporation technique, macromolecule device is then using rotary coating or spraying typography.
All in all, the direction of following OLED be develop high efficiency, high brightness, the long-life, low cost white light parts and
Full color display device, but the technological industrialization process still faces many key issues.Therefore, design and a kind of chemical combination of searching
Thing, occurs to overcome the shortcomings of it as OLED new materials in actual application, in being OLED material research work
Emphasis and Development Trend from now on.
The content of the invention
It is an object of the invention to provide a kind of carbazole analog derivative and its preparation method and application, it is organic that the present invention is provided
Compound thermal stability is high, preparation method simple, and the organic luminescent device being made up of the compound shows luminous efficiency
Height, the advantage of long lifespan is the luminous organic material of function admirable.
Present invention firstly provides a kind of carbazole analog derivative, structural formula is：
Wherein, R1 is selected from the aryl of substituted or unsubstituted C6-C60, the condensed ring of substituted or unsubstituted C10~C60, takes
One kind in the condensed hetero ring of generation or unsubstituted C8~C60；R2, R3, R4, R5 independence selected from hydrogen, substituted or unsubstituted C6-
One kind in the aryl of C60.
Preferably, the R1Aryl, substituted or unsubstituted C10~C30 selected from substituted or unsubstituted C6-C30
One kind in condensed ring, the condensed hetero ring of substituted or unsubstituted C8~C30；R2、R3、R4、R5It is independent selected from hydrogen, substitution or not take
One kind in the aryl of the C6-C30 in generation.
Preferably, the R1For the aryl of substituted or unsubstituted C6~C18, substituted or unsubstituted C10~C24 it is thick
One kind in ring, the condensed hetero ring of substituted or unsubstituted C18~C24.
Preferably, the R2、R3、R4、R5It is hydrogen.
Preferably, the R1Selected from phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, xenyl, terphenyl, indenyl, fluorenyl,
The fluorenyl of spiral shell two or N- phenyl carbazole bases.
Preferably, the carbazole analog derivative is selected from any one in structure shown in following TM1~TM15：
The present invention also provides a kind of preparation method of carbazole analog derivative, and syntheti c route is as follows：
Wherein, R1In aryl, the condensed ring of substituted or unsubstituted C10~C60 selected from substituted or unsubstituted C6-C60,
One kind of the condensed hetero ring of substituted or unsubstituted C8~C60；R2、R3、R4、R5It is independent selected from hydrogen, substituted or unsubstituted C6-
One kind in the aryl of C60.
The present invention also provides application of the carbazole analog derivative in organic electroluminescence device.
Preferably, the organic electroluminescence device includes anode, negative electrode and organic matter layer, contains in the organic matter layer
Described carbazole analog derivative.
Preferably, the organic matter layer includes hole transmission layer, spreads out containing described carbazoles in hole transmission layer
It is biological.
Beneficial effects of the present invention:
Present invention firstly provides a kind of carbazole analog derivative, the carbazole analog derivative has structure shown in formula I, by introducing
Condensed ring class rigidity, close packed structure, make the carbazole analog derivative thermal stability obtained by the present invention high, can be used to prepare Organic Electricity
Electroluminescence device, especially as the hole mobile material in organic electroluminescence device, shows that luminous efficiency is high, long lifespan
Advantage, better than existing conventional OLED.The present invention also provides a kind of preparation method of carbazole analog derivative, the preparation method
Simply, raw material is easy to get, the need for disclosure satisfy that industrialization development.Carbazole analog derivative of the present invention has in OLED luminescent devices
Good application effect, with good industrialization prospect.
Specific embodiment
For a further understanding of the present invention, the preferred embodiment of the invention is described with reference to embodiment, but
It should be appreciated that these descriptions are simply to further illustrate the features and advantages of the present invention, rather than to the claims in the present invention
Limitation.
Present invention firstly provides a kind of carbazole analog derivative, structural formula is：
Wherein, R1Aryl, the condensed ring of substituted or unsubstituted C10~C60 selected from substituted or unsubstituted C6-C60, take
One kind in the condensed hetero ring of generation or unsubstituted C8~C60；R2、R3、R4、R5It is independent selected from hydrogen, substituted or unsubstituted C6-
One kind in the aryl of C60.
Preferably R1Aryl, the condensed ring of substituted or unsubstituted C10~C30 selected from substituted or unsubstituted C6-C30,
One kind in the condensed hetero ring of substituted or unsubstituted C8~C30；R2、R3、R4、R5It is independent selected from hydrogen, it is substituted or unsubstituted
One kind in the aryl of C6-C30.
According to the present invention, in described substituted aryl, the condensed ring of substitution, the condensed hetero ring of substitution, replace the choosing of base independence
From alkyl, alkoxy, amino, halogen, cyano group, nitro, hydroxyl or sulfydryl.
Further preferably R1For the aryl of substituted or unsubstituted C6~C18, the condensed ring of substituted or unsubstituted C10~C24, take
One kind in the condensed hetero ring of generation or unsubstituted C18~C24.
Further preferably R2、R3、R4、R5It is hydrogen.
Most preferably R1Selected from phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, xenyl, terphenyl, indenyl, fluorenyl, the fluorenes of spiral shell two
Base or N- phenyl carbazole bases.
Specifically, the carbazole analog derivative is preferably selected from any one in structure shown in following TM1~TM15：
The present invention also provides a kind of preparation method of carbazole analog derivative, and syntheti c route is as follows：
Wherein, R1In aryl, the condensed ring of substituted or unsubstituted C10~C60 selected from substituted or unsubstituted C6-C60,
One kind of the condensed hetero ring of substituted or unsubstituted C8~C60；R2、R3、R4、R5It is independent selected from hydrogen, substituted or unsubstituted C6-
One kind in the aryl of C60.
According to the present invention, the compound shown in intermediate A is prepared according to method as follows：
Chlorinated diphenyl base phosphorus obtains intermediate A with bromo carbazole reaction.
According to the present invention, the compound shown in target product is prepared according to method as follows：
Under nitrogen protection, palladium and tri-butyl phosphine are catalyst, in the case that sodium tert-butoxide is alkali, intermediate A
With halides target product is obtained via Buchwald-Hartwig coupling reactions.
According to the present invention, the compound and halides shown in intermediate A are obtained by coupling reaction under nitrogen protection
Shown carbazole analog derivative, the present invention does not have special limitation to the coupling reaction, ripe using those skilled in the art institute
The coupling reaction known, the preparation method is simple, and raw material is easy to get.
The present invention also provides application of the carbazole analog derivative in organic electroluminescence device, carbazoles of the invention
Derivative can be applied as hole mobile material in terms of organic electroluminescence device, the organic electroluminescence device
Including anode, negative electrode and organic matter layer, organic matter layer comprising hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer,
At least one of which in hole blocking layer, electron transfer layer, electron injecting layer；At least one of which in the organic matter layer contains above-mentioned
Described carbazole analog derivative.The carbazole analog derivative specifically can be as the hole transport for preparing organic electroluminescence device
Layer.The device architecture of use is preferably specially：BH1 and BD1 is used as luminescent layer material, and Alq3 is used as electron-transporting material, described
Carbazole analog derivative be used as hole transmission layer material, be used to manufacture the organic luminescent device of construction same as below：ITO/ institutes
Carbazole analog derivative/the BH1 for stating:BD1/Alq3/LiF/Al.The organic electroluminescence device can be used for flat-panel monitor, shine
The application fields such as Mingguang City source, direction board, signal lamp.
The present invention has no particular limits to the raw material employed in following examples, can be for commercially available prod or using this
Preparation method known to art personnel is prepared.
Embodiment A：
The preparation of intermediate A 1
By compound b be dissolved in anhydrous tetrahydro furan with mol ratio be 1:2 be dissolved in the n-BuLi of n-hexane, in nitrogen
Under atmosphere, -78 DEG C of stirring reaction 3h.Then by compound a chlorinated diphenyl base phosphorus, (compound a is 1 with the mol ratio of compound b:
2) it is added in above-mentioned solution and reacts 3h, then allow temperature slowly to go back up to room temperature (12h), is subsequently adding methyl alcohol and terminates anti-
Should.Extracted with dichloromethane, merge organic phase, dried with anhydrous magnesium sulfate, filtering, removal of solvent under reduced pressure obtains crude product, silica gel
Column chromatography obtains white solid.
Mass spectrum m/z：401.16 (calculated values：401.13).Theoretical elemental content (%) C28H20NP：C,83.77；H,5.02；
N,3.49；P, 7.72 actual measurements constituent content (%)：C,83.76；H,5.02；N,3.50；P,7.72.The above results confirm to be produced
Thing is target product.
Embodiment C：
(1) synthesis of compound TM1：
By tri-butyl phosphine (toluene solution of the 1.0M of 3mL, 7.32mmol), palladium (0.4g, 1.83mmol) and uncle
Sodium butoxide (22.8g, 238mmol) exists added to intermediate A 1 (73.3g, 183mmol) and 4- bromo biphenyls (46.4g, 201mmol)
Solution in degassed toluene (500mL), and the mixture is heated 2 hours under reflux.The reactant mixture is cooled to
Room temperature, filters with dilution with toluene and via diatomite.By filtrate water dilution, and extracted with toluene, and merge organic
Phase, it is evaporated under vacuo.The residue is filtered via silica gel, target product TM1 is recrystallized to give
(91.0g, theoretical value 90%).
Mass spectrum m/z：553.15 (calculated values：553.20).Theoretical elemental content (%) C40H28NP：C,86.78；H,5.10；
N,2.53；P, 5.59 actual measurements constituent content (%)：C,86.79；H,5.11；N,2.52；P,5.58.The above results confirm to be produced
Thing is target product.
(2) synthesis of compound TM2：
4- bromo biphenyls in (1) are replaced with into 4- bromine para-terpheny, other steps are identical with (1), obtain 71.1g chemical combination
Thing TM2, yield 87%.
Mass spectrum m/z：629.25 (calculated values：629.23).Theoretical elemental content (%) C46H32NP：C,87.74；H,5.12；
N,2.22；P, 4.92 actual measurements constituent content (%)：C,87.73；H,5.11；N,2.23；P,4.93.The above results confirm to be produced
Thing is target product.
(3) synthesis of compound TM3：
4- bromo biphenyls in (1) are replaced with into bromo- 9, the 9- dimethyl fluorenes of 2-, other steps are identical with (1), obtain
92.2g compound TM3, yield 85%.
Mass spectrum m/z：593.25 (calculated values：593.23).Theoretical elemental content (%) C43H32NP：C,86.99；H,5.43；
N,2.36；P, 5.22 actual measurements constituent content (%)：C,86.97；H,5.44；N,2.36；P,5.23.The above results confirm to be produced
Thing is target product.
(4) synthesis of compound TM4：
4- bromo biphenyls in (1) are replaced with into 2- (4- bromophenyls) -9,9- dimethyl fluorenes, other steps are identical with (1),
Obtain 97.9g compound TM4, yield 80%.
Mass spectrum m/z：669.25 (calculated values：669.26).Theoretical elemental content (%) C49H36NP：C,87.87；H,5.42；
N,2.09；P, 4.62 actual measurements constituent content (%)：C,87.88；H,5.42；N,2.07；P,4.63.The above results confirm to be produced
Thing is target product.
(5) synthesis of compound TM5：
4- bromo biphenyls in (1) are replaced with into 2- (4- bromophenyls) -9,9- diphenylfluorenes, other steps are identical with (1),
Obtain 116.1g compound TM5, yield 80%.
Mass spectrum m/z：793.25 (calculated values：793.29).Theoretical elemental content (%) C59H40NP：C,89.26；H,5.08；
N,1.76；P, 3.90 actual measurements constituent content (%)：C,89.24；H,5.09；N,1.76；P,3.91.The above results confirm to be produced
Thing is target product.
(6) synthesis of compound TM6：
4- bromo biphenyls in (1) are replaced with into 2- (4- bromophenyls)-fluorenes of 9,9- spiral shells two, other steps are identical with (1), obtain
To 108.5g compound TM6, yield 75%.
Mass spectrum m/z：791.25 (calculated values：791.27).Theoretical elemental content (%) C59H38NP：C,89.48；H,4.84；
N,1.77；P, 3.91 actual measurements constituent content (%)：C,89.47；H,4.83；N,1.79；P,3.91.The above results confirm to be produced
Thing is target product.
(7) synthesis of compound TM7：
4- bromo biphenyls in (1) are replaced with into the bromo- 9- phenyl carbazoles of 2-, other steps are identical with (1), obtain 93.9g
Compound TM7, yield 80%.
Mass spectrum m/z：642.25 (calculated values：642.22).Theoretical elemental content (%) C46H31N2P：C,85.96；H,4.86；
N,4.36；P, 4.82 actual measurements constituent content (%)：C,85.95；H,4.84；N,4.37；P,4.86.The above results confirm to be produced
Thing is target product.
(8) synthesis of compound TM8：
4- bromo biphenyls in (1) are replaced with into the bromo- 9- phenyl carbazoles of 3-, other steps are identical with (1), obtain 93.9g
Compound TM8, yield 80%.
Mass spectrum m/z：642.25 (calculated values：642.22).Theoretical elemental content (%) C46H31N2P：C,85.96；H,4.86；
N,4.36；P, 4.82 actual measurements constituent content (%)：C,85.95；H,4.84；N,4.37；P,4.86.The above results confirm to be produced
Thing is target product.
(9) synthesis of compound TM9：
4- bromo biphenyls in (1) are replaced with into the bromo- 9- of 2- (phenyl -2,3,4,5,6- deuteriums)-carbazole, other steps with
(1) it is identical, obtain 82.8g compound TM9, yield 70%.
Mass spectrum m/z：647.23 (calculated values：647.25).Theoretical elemental content (%) C46H26D5N2P：C,85.29；H,
5.60；N,4.32；P, 4.78 actual measurements constituent content (%)：C,85.30；H,5.60；N,4.32；P,4.77.The above results are confirmed
Acquisition product is target product.
(10) synthesis of compound TM10：
4- bromo biphenyls in (1) are replaced with into 2- (4- bromophenyls) -9- phenyl carbazoles, other steps are identical with (1), obtain
To 105.1g compound TM10, yield 80%.
Mass spectrum m/z：718.21 (calculated values：718.25).Theoretical elemental content (%) C52H35N2P：C,86.89；H,4.91；
N,3.90；P, 4.31 actual measurements constituent content (%)：C,86.88；H,4.91；N,3.90；P,4.31.The above results confirm to be produced
Thing is target product.
(11) synthesis of compound TM11：
4- bromo biphenyls in (1) are replaced with into 9- (4- bromophenyls)-carbazole, other steps are identical with (1), obtain
96.3g compound TM11, yield 82%.
Mass spectrum m/z：642.25 (calculated values：642.22).Theoretical elemental content (%) C46H31N2P：C,85.96；H,4.86；
N,4.36；P, 4.82 actual measurements constituent content (%)：C,85.95；H,4.85；N,4.37；P,4.83.The above results confirm to be produced
Thing is target product.
(12) synthesis of compound TM12：
4- bromo biphenyls in (1) are replaced with into 9- (4 '-bromine [1,1 '-phenyl] -3- bases)-carbazole, other steps with (1)
It is identical, obtain 98.5g compound TM12, yield 75%.
Mass spectrum m/z：718.21 (calculated values：718.25).Theoretical elemental content (%) C52H35N2P：C,86.89；H,4.91；
N,3.90；P, 4.31 actual measurements constituent content (%)：C,86.87；H,4.92；N,3.90；P,4.31.The above results confirm to be produced
Thing is target product.
(13) synthesis of compound TM13：
4- bromo biphenyls in (1) are replaced with into 3- (4- bromophenyls) -9- phenyl carbazoles, other steps are identical with (1), obtain
To 98.5g compound TM13, yield 70%.
Mass spectrum m/z：718.21 (calculated values：718.25).Theoretical elemental content (%) C52H35N2P：C,86.89；H,4.91；
N,3.90；P, 4.31 actual measurements constituent content (%)：C,86.87；H,4.91；N,3.92；P,4.30.The above results confirm to be produced
Thing is target product.
(14) synthesis of compound TM14：
4- bromo biphenyls in (1) are replaced with into 1- bromine pyrenes, other steps are identical with (1), obtain 87.9g compounds
TM14, yield 80%.
Mass spectrum m/z：601.25 (calculated values：601.20).Theoretical elemental content (%) C44H28NP：C,87.83；H,4.69；
N,2.33；P, 5.15 actual measurements constituent content (%)：C,87.84；H,4.67；N,2.33；P,5.16.The above results confirm to be produced
Thing is target product.
(15) synthesis of compound TM15：
4- bromo biphenyls in (1) are replaced with into the bromo- indenes of 6-, other steps are identical with (1), obtain 65.9g compounds
TM15, yield 70%.
Mass spectrum m/z：515.15 (calculated values：515.18).Theoretical elemental content (%) C37H26NP：C,86.19；H,5.08；
N,2.72；P, 6.01 actual measurements constituent content (%)：C,86.17；H,5.08；N,2.73；P,6.02.The above results confirm to be produced
Thing is target product.
Contrast Application Example：
Transparent anode electrode ito substrate is cleaned by ultrasonic 15 minutes in isopropanol, and is exposed 30 minutes under ultraviolet light,
Then processed 10 minutes with plasma.The ito substrate after treatment is then put into evaporated device.One layer of 30nm's of evaporation first
NPB as hole transmission layer, followed by luminescent layer evaporation, the BD1 of mixing evaporation BH1 and 5%, the then Alq3 of evaporation 30nm
As electron transfer layer, 0.5nm LiF are then deposited with again, then the metal Al of evaporation 60nm.
Application Example 1
Transparent anode electrode ito substrate is cleaned by ultrasonic 15 minutes in isopropanol, and is exposed 30 minutes under ultraviolet light,
Then processed 10 minutes with plasma.The ito substrate after treatment is then put into evaporated device.One layer of 30nm's of evaporation first
TM7 is then deposited with the Alq3 of 30nm as hole transmission layer followed by the evaporation of luminescent layer, the BD1 of mixing evaporation BH1 and 5%
As electron transfer layer, 0.5nm LiF are then deposited with again, then the metal Al of evaporation 60nm.
Application Example 2
Change the TM7 in Application Example 1 into TM11.
Application Example 3
Change the TM7 in Application Example 1 into TM14.
OLED is produced as follows：
Contrast Application Example：ITO/NPB/BH1:BD1/Alq3/LiF/Al；
Application Example 1：ITO/TM7/BH1:BD1/Alq3/LiF/Al；
Application Example 2：ITO/TM11/BH1:BD1/Alq3/LiF/Al；
Application Example 3：ITO/TM14/BH1:BD1/Alq3/LiF/Al；
Under 1000nits, Nan dian Yao device result is as follows：
| Device | Cd/A | Driver Voltage | Life-span (T80) |
| Contrast Application Example | 6cd/A | 4.7V | 101hours |
| Application Example 1 | 7.4cd/A | 4.6V | 213hours |
| Application Example 2 | 7.3cd/A | 4.5V | 323hours |
| Application Example 3 | 7.5cd/A | 4.5V | 195hours |
Result above shows that carbazole analog derivative of the invention is applied in organic electroluminescence device, especially as
Hole mobile material, shows that luminous efficiency is high, long lifespan advantage, is luminous organic material of good performance.
Obviously, the explanation of above example is only intended to help and understands the method for the present invention and its core concept.Should refer to
Go out, for the those of ordinary skill of the technical field, under the premise without departing from the principles of the invention, can also be to this hair
Bright to carry out some improvement and modification, these are improved and modification is also fallen into the protection domain of the claims in the present invention.
Claims (10)
1. a kind of carbazole analog derivative, it is characterised in that with the structure as shown in formula (I)：
Wherein, R1Aryl, the condensed ring of substituted or unsubstituted C10~C60 selected from substituted or unsubstituted C6-C60, substitution or
One kind in the condensed hetero ring of unsubstituted C8~C60；R2、R3、R4、R5It is independent selected from hydrogen, substituted or unsubstituted C6-C60
One kind in aryl.
2. a kind of carbazole analog derivative according to claim 1, it is characterised in that R1Selected from substituted or unsubstituted C6-
One kind in the aryl of C30, the condensed ring of substituted or unsubstituted C10~C30, the condensed hetero ring of substituted or unsubstituted C8~C30；
R2、R3、R4、R5It is independent selected from the one kind in hydrogen, the aryl of substituted or unsubstituted C6-C30.
3. a kind of carbazole analog derivative according to claim 1, it is characterised in that R1It is substituted or unsubstituted C6~C18
Aryl, the condensed ring of substituted or unsubstituted C10~C24, the condensed hetero ring of substituted or unsubstituted C18~C24 in one kind.
4. a kind of carbazole analog derivative according to claim 1, it is characterised in that R2、R3、R4、R5It is hydrogen.
5. a kind of carbazole analog derivative according to claim 1, it is characterised in that R1Selected from phenyl, naphthyl, anthryl, phenanthrene
Base, pyrenyl, xenyl, terphenyl, indenyl, fluorenyl, the fluorenyl of spiral shell two or N- phenyl carbazole bases.
6. a kind of carbazole analog derivative according to claim 1, it is characterised in that the carbazole analog derivative is selected from as follows
Any one in structure shown in TM1~TM15：
7. the preparation method of the carbazole analog derivative described in any one of claim 1-6, it is characterised in that closed by following route
Into obtaining the carbazole analog derivative：
Wherein, R1In aryl, the condensed ring of substituted or unsubstituted C10~C60 selected from substituted or unsubstituted C6-C60, replace
Or one kind of the condensed hetero ring of unsubstituted C8~C60；R2、R3、R4、R5It is independent selected from hydrogen, substituted or unsubstituted C6-C60
One kind in aryl.
8. application of the carbazole analog derivative described in claim 1-6 any one in organic electroluminescence device.
9. application of the carbazole analog derivative according to right wants 8 in organic electroluminescence device, it is characterised in that described
Organic electroluminescence device includes anode, negative electrode and organic matter layer, and any one of claim 1~6 is contained in the organic matter layer
Described carbazole analog derivative.
10. application of the carbazole analog derivative according to claim 9 in organic electroluminescence device, it is characterised in that
The organic matter layer includes hole transmission layer, derives containing the carbazoles described in any one of claim 1~6 in hole transmission layer
Thing.
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| CN107629062A (en) * | 2017-10-09 | 2018-01-26 | 长春海谱润斯科技有限公司 | A kind of carbazole analog derivative and its organic luminescent device |
| CN107698486A (en) * | 2017-10-09 | 2018-02-16 | 长春海谱润斯科技有限公司 | A kind of benzo carbazole organic compound and its organic luminescent device |
| CN107698489A (en) * | 2017-10-23 | 2018-02-16 | 长春海谱润斯科技有限公司 | A kind of compound and its organic luminescent device of benzo carbazole class |
| CN107698488A (en) * | 2017-10-09 | 2018-02-16 | 长春海谱润斯科技有限公司 | A kind of benzo carbazole analog derivative and its organic luminescent device |
| CN114853702A (en) * | 2022-06-07 | 2022-08-05 | 阜阳欣奕华材料科技有限公司 | Naphthalene heteroaromatic compound, organic electroluminescent device and display device |
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Cited By (6)
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| CN107602440A (en) * | 2017-10-09 | 2018-01-19 | 长春海谱润斯科技有限公司 | A kind of benzo carbazole class electroluminescent organic material and its organic luminescent device |
| CN107629062A (en) * | 2017-10-09 | 2018-01-26 | 长春海谱润斯科技有限公司 | A kind of carbazole analog derivative and its organic luminescent device |
| CN107698486A (en) * | 2017-10-09 | 2018-02-16 | 长春海谱润斯科技有限公司 | A kind of benzo carbazole organic compound and its organic luminescent device |
| CN107698488A (en) * | 2017-10-09 | 2018-02-16 | 长春海谱润斯科技有限公司 | A kind of benzo carbazole analog derivative and its organic luminescent device |
| CN107698489A (en) * | 2017-10-23 | 2018-02-16 | 长春海谱润斯科技有限公司 | A kind of compound and its organic luminescent device of benzo carbazole class |
| CN114853702A (en) * | 2022-06-07 | 2022-08-05 | 阜阳欣奕华材料科技有限公司 | Naphthalene heteroaromatic compound, organic electroluminescent device and display device |
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