CN117986218A - Spiro compound, application thereof and organic electroluminescent element - Google Patents
Spiro compound, application thereof and organic electroluminescent element Download PDFInfo
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- CN117986218A CN117986218A CN202211349534.6A CN202211349534A CN117986218A CN 117986218 A CN117986218 A CN 117986218A CN 202211349534 A CN202211349534 A CN 202211349534A CN 117986218 A CN117986218 A CN 117986218A
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- 150000003413 spiro compounds Chemical class 0.000 title claims abstract description 52
- 239000000463 material Substances 0.000 claims abstract description 43
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- 230000005525 hole transport Effects 0.000 claims abstract description 28
- 238000002347 injection Methods 0.000 claims description 13
- 239000007924 injection Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000000758 substrate Substances 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 4
- -1 dibenzofuranyl Chemical group 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000005549 heteroarylene group Chemical group 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 abstract description 3
- 150000004982 aromatic amines Chemical class 0.000 abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 90
- 239000000543 intermediate Substances 0.000 description 26
- 239000007787 solid Substances 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 238000000151 deposition Methods 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 239000011521 glass Substances 0.000 description 9
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 229910052769 Ytterbium Inorganic materials 0.000 description 4
- 238000004042 decolorization Methods 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 235000011056 potassium acetate Nutrition 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 4
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 4
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 3
- BMIBJCFFZPYJHF-UHFFFAOYSA-N 2-methoxy-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound COC1=NC=C(C)C=C1B1OC(C)(C)C(C)(C)O1 BMIBJCFFZPYJHF-UHFFFAOYSA-N 0.000 description 3
- BMVWCPGVLSILMU-UHFFFAOYSA-N 5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-one Chemical compound C1CC2=CC=CC=C2C(=O)C2=CC=CC=C21 BMVWCPGVLSILMU-UHFFFAOYSA-N 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 3
- ZXHUJRZYLRVVNP-UHFFFAOYSA-N dibenzofuran-4-ylboronic acid Chemical compound C12=CC=CC=C2OC2=C1C=CC=C2B(O)O ZXHUJRZYLRVVNP-UHFFFAOYSA-N 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 229910001316 Ag alloy Inorganic materials 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- VBXDEEVJTYBRJJ-UHFFFAOYSA-N diboronic acid Chemical compound OBOBO VBXDEEVJTYBRJJ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 2
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- GIMVCZMZRZGDTL-UHFFFAOYSA-N 1-bromo-3-chloro-2-iodobenzene Chemical compound ClC1=CC=CC(Br)=C1I GIMVCZMZRZGDTL-UHFFFAOYSA-N 0.000 description 1
- ROJJKFAXAOCLKK-UHFFFAOYSA-N 1-bromo-4-chloro-2-iodobenzene Chemical compound ClC1=CC=C(Br)C(I)=C1 ROJJKFAXAOCLKK-UHFFFAOYSA-N 0.000 description 1
- YYKBFGMYHQMXIL-UHFFFAOYSA-N 1-phenyl-2,3,4-tri(propan-2-yl)benzene Chemical group CC(C)C1=C(C(C)C)C(C(C)C)=CC=C1C1=CC=CC=C1 YYKBFGMYHQMXIL-UHFFFAOYSA-N 0.000 description 1
- CXHXFDQEFKFYQJ-UHFFFAOYSA-N 2-bromo-4-chloro-1-iodobenzene Chemical compound ClC1=CC=C(I)C(Br)=C1 CXHXFDQEFKFYQJ-UHFFFAOYSA-N 0.000 description 1
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 1
- CSFNUYPFWSRMET-UHFFFAOYSA-N 3-phenyl-n-(4-phenylphenyl)aniline Chemical compound C=1C=CC(C=2C=CC=CC=2)=CC=1NC(C=C1)=CC=C1C1=CC=CC=C1 CSFNUYPFWSRMET-UHFFFAOYSA-N 0.000 description 1
- QRXMUCSWCMTJGU-UHFFFAOYSA-N 5-bromo-4-chloro-3-indolyl phosphate Chemical compound C1=C(Br)C(Cl)=C2C(OP(O)(=O)O)=CNC2=C1 QRXMUCSWCMTJGU-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
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- Electroluminescent Light Sources (AREA)
Abstract
The application provides a spiro compound and application thereof as well as an organic electroluminescent element, wherein the spiro compound has a structure shown in a formula (A), and by applying the technical scheme of the application, the spiro compound with the structure shown in the formula (A) has stronger rigidity by taking a benzofuran ring structure as a parent nucleus, so that the thermal stability of the spiro compound is greatly improved. On the other hand, aromatic amine or nitrogen-containing heterocycle is introduced into the parent nucleus, so that the compound can be used as a hole transport material or an electron transport material. The spiro compound provided by the application is applied to an organic electroluminescent element, can effectively reduce the working voltage of the organic electroluminescent element, and can improve the luminous efficiency and the service life of the element.
Description
Technical Field
The invention relates to the technical field of organic electroluminescent elements, in particular to a spiro compound and application thereof, and an organic electroluminescent element.
Background
Organic LIGHT EMITTING Diodes (OLEDs) have advantages of light weight, thin thickness, self-luminescence, low power consumption, no backlight source, wide viewing angle, fast response, flexibility, etc., have gradually replaced liquid crystal display panels as new generation flat panel displays, and have great potential in flexible display. However, to date, OLED devices have not achieved full-scale popularization applications, where efficiency and lifetime of the device are important reasons limiting its popularity.
The OLED currently used in industrialization generally includes a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and other film layers, which relate to various organic photoelectric materials, and the physical and chemical properties of the materials are closely related to the performance of the device, so that the device optimization can be realized through reasonable matching. The hole transport materials and the electron transport materials are most widely researched, the hole transport materials are mostly aromatic amine compounds, the electron transport materials are mostly nitrogen-containing heterocyclic compounds, and the mother nucleus structure of the spiro ring is of a non-planar rigid conjugated structure, so that the heat stability is good, the hole transport materials and the electron transport materials are more structures researched at present, and the hole transport materials and the electron transport materials with more excellent development performance are still research hot spots in the field of OLED materials at present.
In view of this, the present application has been made.
Disclosure of Invention
The main object of the present invention is to provide a spiro compound, its application and an organic electroluminescent device, so that the application of the spiro compound in the organic electroluminescent device improves the problem that the efficiency and the service life of the organic electroluminescent device limit the popularization thereof.
In order to achieve the above object, according to one aspect of the present invention, there is provided a spiro compound having a structure represented by formula (a):
M is selected from formula (I) or formula (II);
Wherein HAr is selected from substituted or unsubstituted C3 to C20 nitrogen containing heteroaryl; ar 1 and Ar 2 are each independently selected from substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C6-C18 heteroaryl; l 1 and L 2 are each independently selected from the group consisting of a direct bond, a substituted or unsubstituted C6-C18 arylene, and a substituted or unsubstituted C6-C18 heteroarylene.
According to another aspect of the present invention there is provided the use of the spiro compound as described above in a hole transporting material or an electron transporting material.
According to a third aspect of the present invention, there is also provided an organic electroluminescent element comprising a substrate layer, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and a cathode layer, the material of the hole transport layer or the electron transport layer comprising any one of the spiro compounds provided in the first aspect.
By applying the technical scheme of the application, the spiro compound with the structure shown in the formula (A) has stronger rigidity by taking the benzofuran ring structure as a mother nucleus, so that the thermal stability of the spiro compound is greatly improved. On the other hand, aromatic amine or nitrogen-containing heterocycle is introduced into the parent nucleus, so that the compound can be used as a hole transport material or an electron transport material. The spiro compound provided by the application is applied to an organic electroluminescent element, can effectively reduce the working voltage of the organic electroluminescent element, and can improve the luminous efficiency and the service life of the element.
Drawings
The accompanying drawings, which are included to provide a further understanding of the application and are incorporated in and constitute a part of this specification, illustrate embodiments of the application and together with the description serve to explain the application. In the drawings:
Fig. 1 shows a schematic structure of an organic electroluminescent element provided in embodiment 1 of a device provided according to the present invention;
wherein the above figures include the following reference numerals:
1. A substrate layer; 2. a hole injection layer; 3. a hole transport layer; 4. a light emitting layer; 5. an electron transport layer; 6. and a cathode layer.
Detailed Description
It should be noted that, without conflict, the embodiments of the present application and features of the embodiments may be combined with each other. The present application will be described in detail with reference to examples.
As analyzed in the background art of the present application, the efficiency and lifetime of the existing organic electroluminescent device are important factors limiting its popularization, and in order to improve the efficiency and lifetime of the organic electroluminescent device, the present application provides a spiro compound and its application, and the organic electroluminescent device.
In a first exemplary embodiment of the present application, there is provided a spiro compound having a structure represented by the following formula (a):
Wherein M is selected from formula (I) or formula (II);
The HAr is selected from substituted or unsubstituted C3 to C20 nitrogen-containing heteroaryl; ar 1 and Ar 2 are each independently selected from substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C6-C18 heteroaryl; l 1 and L 2 are each independently selected from the group consisting of a direct bond, a substituted or unsubstituted C6-C18 arylene, and a substituted or unsubstituted C6-C18 heteroarylene.
By applying the technical scheme of the application, the spiro compound with the structure shown in the formula (A) has stronger rigidity by taking the benzofuran ring structure as a mother nucleus, so that the thermal stability of the spiro compound is greatly improved. On the other hand, aromatic amine or nitrogen-containing heterocycle is introduced into the parent nucleus, so that the compound can be used as a hole transport material or an electron transport material. The spiro compound provided by the application is applied to an organic electroluminescent element, can effectively reduce the working voltage of the organic electroluminescent element, and can improve the luminous efficiency and the service life of the element.
In the present application, when HAr is a substituted C3 to C20 nitrogen-containing heteroaryl, the substituents include, but are not limited to, C1 to C20 linear or branched alkyl groups. When Ar 1 and Ar 2 are each independently substituted aryl or heteroaryl, the substituents include, but are not limited to, C1-C18 straight or branched chain alkyl groups. When L and L 2 are each independently a substituted C6-C18 arylene or heteroarylene group, the substituents include, but are not limited to, C1-C18 straight or branched alkyl groups.
In some embodiments of the present application, when the spiro compound is applied to an electron transport material or a hole transport material, at least one of the following formulas (a-1) to (a-6) can further effectively reduce the operating voltage of the organic electroluminescent device, and further improve the luminous efficiency and the service life.
In the above formulae (A-1) to (A-6), HAr and Ar 1、Ar2、L1、L2 have the same meanings as described above, and are not described here again.
In some embodiments of the present application, when HAr is selected from substituted or unsubstituted C3 to C12 nitrogen-containing heteroaryl groups, the spiro compound is applied to an electron transport material, and the prepared organic electroluminescent element can further reduce the driving voltage, thereby further improving the luminous efficiency and the service life of the organic electroluminescent element. Especially when HAr is substituted or unsubstituted C3-C8 nitrogen-containing heteroaryl, the HAr is applied to an electron transport material, and the prepared organic electroluminescent element has lower driving voltage, thereby further improving luminous efficiency and prolonging service life.
In some embodiments of the present application, when HAr is at least one selected from the formulas (HAr-1) to (HAr-10), and is applied to an electron transport material or when the HAr is applied, the prepared organic electroluminescent element can further reduce a driving voltage, thereby more effectively improving the luminous efficiency and the service life of the organic electronic element.
In the above formulae (HAr-1) to (HAr-10), Z is selected from the group consisting of a dotted line representing a bond; z is at least one selected from H, CN, halogen, substituted or unsubstituted C 1～C10 linear alkyl, substituted or unsubstituted C 3～C10 branched alkyl, substituted or unsubstituted C 6～C18 aryl, substituted or unsubstituted C 6～C18 heteroaryl.
When Z is at least one selected from the group consisting of a substituted or unsubstituted C 1～C5 linear alkyl group, a substituted or unsubstituted C 3～C6 branched alkyl group, a substituted or unsubstituted C 6～C12 aryl group, and a substituted or unsubstituted C 6～C12 heteroaryl group in the above-mentioned (HAr-1) to (HAr-10), the organic electroluminescent element obtained is excellent in luminous efficiency and in service life when it is applied to an electron transport material. Especially when Z is at least one of methyl, phenyl, biphenyl, naphthyl, 9' -dimethylfluorenyl, dibenzofuranyl and dibenzothiophenyl or the combination of the two, and the Z is applied to an electron transport material, the prepared organic electroluminescent element has more excellent luminous efficiency and longer service life.
In some embodiments of the present application, when L 1 and L 2 are each independently selected from a direct bond or a phenylene group, the spiro compound is applied to an electron transport material or a hole transport material, and the prepared organic electroluminescent device has more excellent luminous efficiency and service life.
In some embodiments of the present application, when the spiro compound is at least one of the following compounds A1 to a432, and the spiro compound is applied to an electron transport material or a hole transport material, the prepared organic electroluminescent device has a lower driving voltage, and further has more excellent light emitting efficiency and longer service life.
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After determining the above spiro compounds and their structural features of the present application, it is easy for a person skilled in the art of organic chemistry to determine how to prepare the compounds. The synthetic route for the target compounds is exemplified as follows:
The above-mentioned Pd ((PPH 3)2Cl2) means ditolylphosphine palladium dichloride; tol means toluene; etOH means ethanol; pd 2dba3 means tris (dibenzylideneacetone) dipalladium; naOtBu means sodium t-butoxide; toluene means toluene).
In a second exemplary embodiment of the present application, there is also provided the use of the above spiro compound in a hole transporting material or an electron transporting material.
The spiro compound provided by the application is used as a hole transport material or an electron transport material, and the prepared organic electroluminescent element has lower working voltage, so that the luminous efficiency and the service life of the organic electroluminescent element are improved.
In a third exemplary embodiment of the present application, there is also provided an organic electroluminescent element including a substrate layer, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode layer, the material of the hole transport layer or the electron transport layer including any one of the spiro compounds provided in the first exemplary embodiment of the present application.
The organic electroluminescent element provided by the application adopts the spiro compound as the main material of the hole transmission layer or the electron transmission layer, so that the driving voltage can be effectively reduced, the luminous efficiency can be further effectively improved, and the service life can be prolonged.
In order to further improve the light-emitting efficiency and extend the service life of the organic electroluminescent element, it is preferable that the electron transport layer includes a spiro compound, and the mass content of the spiro compound is 20% to 80%.
Typically, but not by way of limitation, the mass content of the spiro compound in the electron transport layer is, for example, 20%, 30%, 40%, 45%, 50%, 55%, 60%, 70%, 80% or any two values in the range of values.
The advantageous effects of the present application will be further described below with reference to examples and comparative examples.
In the following examples and comparative examples, "%" is abbreviated "% by weight", TFA means trifluoroacetic acid, and Pd 2(dba)3 means tris (dibenzylideneacetone) dipalladium; X-Phos refers to 2-dicyclohexylphosphorus-2 ',4',6' triisopropylbiphenyl; KOAc refers to potassium acetate; tol refers to toluene; etOH refers to ethanol; pd ((PPH 3)2Cl2) refers to ditolylphosphine palladium dichloride; "B 2Pin2" refers to pinacol bisborate).
1.1 Synthesis of intermediate MA
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2-Bromo-4-chloroiodobenzene (63.4 g,200 mmol), dibenzofuran-4-boronic acid (44.5 g,210 mmol), 200mL of toluene, 50mL of ethanol, 100mL of water and potassium carbonate (55.2 g,400 mmol) are added into a 500mL round bottom flask, stirring and heating to 40 ℃ under the protection of nitrogen, catalyst Pd (PPh 3)2Cl2 (1.4 g,2 mmol) is added, the reaction is stopped after the mixture is continuously heated to reflux reaction for 3h, water is separated while the mixture is hot, the organic phase is dissolved, toluene is heated to be decolorized by a short silica gel column, then toluene is distilled off by spinning to obtain white solid, 50mL of toluene is added for complete dissolution, 150mL of n-hexane is added dropwise, the solid is stirred and separated out, and the solid is filtered and dried to obtain 54.2g of a white solid intermediate M1 with the yield of 76.4%.
Intermediate M1 (35.7 g,100 mmol) and 200mL THF were added to a 500mL round bottom flask, stirred and cooled to-80 ℃ under nitrogen protection, 2.5M n-butyllithium (48 mL,120 mmol) was added, the temperature was kept for 30 minutes, 5-dibenzosuberone (20.6 g,100 mmol) was added for one hour and then cooled to room temperature, 100mL of saturated aqueous ammonium chloride solution was added to quench, 200mL EA was added for extraction, 150mL trifluoroacetic acid was added for reflux reaction for 1.5 hours after cooling to room temperature and ethanol was added for dilution filtration, filtered toluene was thermally dissolved in a short silica gel column for decolorization, toluene was distilled off until solid was separated out, cooled and stirred, filtered and dried to obtain 28.4g of white solid intermediate MA, yield: 61.3%.
1.2 Synthesis of intermediate MB
Intermediate MA (46.7 g,100 mmol), pinacol ester of biboronate (27.9 g,110 mmol), potassium acetate (14.7 g,150 mmol) and 300mL toluene were added to a 500mL round bottom flask, the mixture was stirred and heated to 40℃under nitrogen protection, pd 2dba3 (0.45 g,0.5 mmol) and XPhos (0.47 g,1 mmol) were added and the reaction was stopped after 4 hours of reflux reaction, the mixture was passed through a short column of silica gel while hot, after the filtrate was desolventized, 30mL toluene was added, 80mL n-hexane was thermally dissolved, and then 47.4g of white solid intermediate MB was separated by cooling, yield: 85.1%.
1.3 Synthesis of intermediate MC
2-Bromo-5-chloro-iodobenzene (63.4 g,200 mmol), dibenzofuran-4-boronic acid (44.5 g,210 mmol), 200mL toluene, 50mL ethanol, 100mL water, and potassium carbonate (55.2 g,400 mmol) were added to a 500mL round bottom flask, stirred under nitrogen to raise the temperature to 40 ℃, catalyst Pd (PPh 3)2Cl2 (1.4 g,2 mmol) was added, the reaction was stopped after continuing to raise the temperature to reflux for 3h, water was separated while hot, the organic phase was desolventized, toluene was heated to a short silica gel column to decolorize, toluene was distilled off by spin to obtain a white solid, 50mL toluene was added to complete dissolution, 150mL n-hexane was added dropwise, the precipitated solid was stirred, filtered and dried to obtain 56.5g of a white solid intermediate IN1-1, yield: 79%.
Intermediate M2 (35.7 g,100 mmol), 200mL THF, and 500mL round bottom flask were added, the mixture was stirred and cooled to-80℃under nitrogen protection, 2.5M n-butyllithium (48 mL,120 mmol) was added, the mixture was kept warm for 30 minutes, 5-dibenzosuberone (20.6 g,100 mmol) was added for 1 hour, the mixture was warmed to room temperature, 100mL of saturated aqueous ammonium chloride solution was added to quench, 200mL EA was added for extraction, 150mL trifluoroacetic acid was added for reflux reaction for 1.5 hours, the mixture was cooled to room temperature, ethanol was added for dilution and filtration, filtered toluene was thermally dissolved in a short silica gel column for decolorization, toluene was distilled off until solid was separated out, the mixture was cooled and stirred, filtered and dried to obtain 31.7g of white solid intermediate MC, yield: 68.2%.
1.4 Synthesis of intermediate MD
Intermediate MC (46.7 g,100 mmol), pinacol ester of diboronic acid (27.9 g,110 mmol), potassium acetate (14.7 g,150 mmol) and 300mL toluene were added to a 500mL round bottom flask, the mixture was stirred and heated to 40℃under nitrogen protection, pd 2dba3 (0.45 g,0.5 mmol), XPhos (0.47 g,1 mmol) were added, the reaction was stopped after 4 hours of reflux reaction, the mixture was passed through a short column of silica gel while it was still hot, after desolventizing the filtrate, 30mL toluene and 80mL n-hexane were added and then dissolved, the mixture was cooled to separate 43g of white solid intermediate MD, yield: 77.5%.
1.5 Synthesis of intermediate ME
2-Bromo-6-chloro-iodobenzene (63.4 g,200 mmol), dibenzofuran-4-boronic acid (44.5 g,210 mmol), 200mL toluene, 50mL ethanol, 100mL water, and potassium carbonate (55.2 g,400 mmol) were added to a 500mL round bottom flask, stirred and warmed to 40℃under nitrogen protection, catalyst Pd (PPh 3)2Cl2 (1.4 g,2 mmol) was added, the reaction was stopped after continuing to warm to reflux for 3h, water was separated while hot, the organic phase was desolventized, toluene was heated to a short silica gel column for decolorization, toluene was distilled off by spin-evaporation to give a white solid, 50mL toluene was added for total dissolution, 150mL n-hexane was added dropwise, the precipitated solid was stirred, filtered and dried to give 39.3g of a white solid intermediate M3, and the yield was 55.3%.
Intermediate M3 (35.7 g,100 mmol) and 200mL THF were added to a 500mL round bottom flask, stirred and cooled to-80 ℃ under nitrogen protection, 2.5M n-butyllithium (48 mL,120 mmol) was added, after 30 minutes of heat preservation, 5-dibenzosuberone (20.6 g,100 mmol) was added and allowed to warm to room temperature after one hour, 100mL of saturated aqueous ammonium chloride solution was added to quench, 200mL EA was added for extraction, 150mL trifluoroacetic acid was added for reflux reaction for 1.5 hours after cooling to room temperature and ethanol was added for dilution filtration, filtered toluene was thermally dissolved in a short silica gel column for decolorization, toluene was distilled off by spinning until solid was precipitated, cooled and stirred, filtered and dried to give 34.5g of white solid intermediate ME, yield: 74%.
1.6 Synthesis of intermediate MF
Intermediate ME (46.7 g,100 mmol), pinacol ester of diboronic acid (27.9 g,110 mmol), potassium acetate (14.7 g,150 mmol) and 300mL toluene were added to a 500mL round bottom flask, the mixture was stirred under nitrogen and heated to 40℃and Pd 2dba3 (0.45 g,0.5 mmol), XPhos (0.47 g,1 mmol) were added, the reaction was stopped after 4 hours of reflux reaction, the mixture was passed through a short column of silica gel while hot, after desolventizing the filtrate, 30mL toluene was added, 80mL n-hexane was hot dissolved, and 49.1g of white solid intermediate MF was separated by cooling down, yield: 88.6%.
2.1 Synthesis of Compound A41
Intermediate MB (5.58 g,10 mmol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (CSA: 3842-55-52.81g,10.5 mmol), 50mL toluene, 10mL ethanol, potassium carbonate (2.76 g,20 mmol), 10mL water were added to a 250mL round bottom flask, stirred under nitrogen to raise the temperature to 40 ℃, catalyst Pd (OAc) 2 (0.02 g,0.1 mmol), XPhos (0.09 g,0.2 mmol) was added, the reaction was continued to stop after reflux for 3h, the solid was filtered after cooling, 100mL chlorobenzene was added to thermally dissolve and then passed through a short column of silica gel, distilled to precipitate a solid, cooled, filtered and dried to give 4.44g of white solid intermediate A41, yield: 67%. MS [ m+h ] + = 664.24.
2.2 Synthesis of Compounds A32, A100, A135, A197, A217, A266 and A424.
Referring to the preparation of compound a41, compounds a32, a100, a135, a197, a217, a266 and a424 were synthesized by reacting with different starting materials and intermediates MB, MD or MF. As shown in table 1 below.
TABLE 1
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2.3 Synthesis of Compound A243
Intermediate IN1-2 (4.67 g,10 mmol), N- [1,1 '-biphenyl ] -3-yl- [1,1' -biphenyl ] -4-amine (3.37 g,10.5 mmol), 50mL toluene, sodium t-butoxide (1.44 g,15 mmol) were added to a 250mL round bottom flask, stirred under nitrogen to raise the temperature to 40 ℃, catalyst Pd2dba3 (0.09 g,0.1 mmol), tri-t-butylphosphine (0.08 g,0.4 mmol) was added, after further heating to reflux for 6h, the reaction was stopped, and the hot silica gel short column was passed through, the filtrate was distilled to precipitate a solid, cooled, filtered and dried to give 6.97g white solid A243, yield: 88%. MS [ m+h ] + = 752.30.
2.4 Synthesis of Compounds A305, A339 and A385.
Referring to the preparation method of compound a243, compounds a305, a339 and a385 were synthesized by reacting intermediate MC or ME with different raw materials. As shown in table 2 below.
TABLE 2
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3. Preparation of organic electroluminescent element
The spiro compound provided by the application is particularly suitable for an electron transport layer or a hole transport layer in an organic electroluminescent element, and the application effect of the spiro compound provided by the application as the electron transport layer or the hole transport layer in the organic electroluminescent element is described in detail by specific examples.
The structural formula of the organic material used therein is as follows:
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as shown in fig. 1, the organic electroluminescent element provided by the present application comprises a glass and transparent conductive layer (ITO) substrate layer 1, a hole injection layer 2, a hole transport layer 3, a light emitting layer 4, an electron transport layer 5, and a cathode layer 6.
Example 1
In this embodiment, an organic electroluminescent device is manufactured by using Sunic sp1710,1710 vapor deposition machine, which comprises the following steps: ultrasonic washing glass substrates (40 mm. Times.40 mm. Times.0.7 mm of Corning glass) coated with ITO (indium tin oxide) having a thickness of 135nm with isopropyl alcohol and pure water, respectively, for 5 minutes, followed by ultraviolet ozone washing, and then transferring the glass substrates into a vacuum deposition chamber as a substrate layer 1; a hole transport material HT1 doped with 4% HD was thermally deposited onto a transparent ITO electrode at a thickness of 20nm in vacuum (about 10 -7 Torr) to form a hole injection layer 2; vacuum depositing HT1 with a thickness of 120nm and HT2 with a thickness of 10nm as hole transport layers 3 on the hole injection layer 2; vacuum depositing BH doped with 4% bd of 25nm as the light emitting layer 4 on the hole transport layer 3; then, carrying out vacuum deposition on a 50% LiQ (8-hydroxyquinoline lithium) -doped compound A32 to form an electron transport layer 5, wherein the thickness is 30nm; finally, sequentially depositing 2nm thick ytterbium (Yb, electron injection layer) and 150nm magnesium-silver alloy with the doping ratio of 10:1 to form a cathode layer 6; finally, the device is transferred from the deposition chamber to a glove box and then encapsulated with a UV curable epoxy and a glass cover plate containing a moisture absorbent.
In the above manufacturing steps, the deposition rates of the organic material, ytterbium metal and Mg metal were maintained at 0.1nm/s, 0.05nm/s and 0.2nm/s, respectively.
The device structure is expressed as: ITO (135 nm)/compound HT1:4% HD (20 nm)/compound HT1 (120 nm)/HT 2 (10 nm)/BH 4% BD (25 nm)/compound A32: liQ (5:5, 30 nm) Yb (2 nm)/Mg: ag (10:1, 150 nm).
Examples 2 to 6
Organic electroluminescent elements 2 to 6 were manufactured in the same manner as in example 1, except that the compound shown in the following table 3 was used instead of the compound a32 in device example 1.
Comparative example 1
An organic electroluminescent element was manufactured in the same manner as in example 1, except that compound ETA was used instead of compound a32 in device example 1.
Test example 1
The organic electroluminescent elements provided in the above examples and comparative examples were respectively measured for operating voltage (V), current efficiency (c.e.), external Quantum Efficiency (EQE), and color coordinates (CIEx, CIEy) and lifetime at a current density of 10mA/cm 2, and specific performance data are shown in table 3 below.
The current efficiency (c.e.), external Quantum Efficiency (EQE), and color coordinates (CIEx, CIEy) of the organic electroluminescent element were measured by the french FS-100GA4 test, and the lifetime LT97 (the time taken for the initial luminance to decay to 3880nits, referenced to the comparative example, normalized) was measured by the french FS-MP96 test, and all measurements were performed in the room temperature atmosphere.
TABLE 3 Table 3
Compared with comparative example 1, the voltage of the organic electroluminescent element prepared by using the spiro compound provided by the application as an electron transport material is reduced, and the efficiency and the service life are obviously improved.
Example 7
The application discloses a manufacturing method of organic electroluminescent element by Sunic sp1710,1710 evaporator, which comprises the following steps: ultrasonic washing glass substrates (40 mm. Times.40 mm. Times.0.7 mm of Corning glass) coated with ITO (indium tin oxide) having a thickness of 135nm with isopropyl alcohol and pure water, respectively, for 5 minutes, followed by ultraviolet ozone washing, and then transferring the glass substrates into a vacuum deposition chamber as a substrate layer 1; compound a243 doped with 4% hd was thermally deposited on the transparent ITO electrode at a thickness of 20nm in vacuum (about 10 -7 Torr) to form hole injection layer 2; vacuum depositing 120nm thick compound a243 and 10nm thick HT2 as hole transport layer 3 on hole injection layer 2; vacuum depositing BH doped with 4% bd of 25nm as the light emitting layer 4 on the hole transport layer 3; then, carrying out vacuum deposition on ET doped with 50% LiQ (8-hydroxyquinoline lithium) to form an electron transport layer 5 with the thickness of 30nm; finally, sequentially depositing 2nm thick ytterbium (Yb, electron injection layer) and 150nm magnesium-silver alloy with the doping ratio of 10:1 to form a cathode layer 6; finally, the device is transferred from the deposition chamber to a glove box and then encapsulated with a UV curable epoxy and a glass cover plate containing a moisture absorbent.
In the above manufacturing steps, the deposition rates of the organic material, ytterbium metal and Mg metal were maintained at 0.1nm/s, 0.05nm/s and 0.2nm/s, respectively.
The structure of the organic electroluminescent element is represented as: ITO (135 nm)/Compound A243:4% HD (20 nm)/Compound A243 (120 nm)/HT 2 (10 nm)/BH 4% BD (25 nm)/Compound ET:LiQ (5:5, 30 nm) Yb (2 nm)/Mg:Ag. (10:1, 150 nm)
Examples 7 to 12
Organic electroluminescent elements 7 to 12 were manufactured in the same manner as in example 1, except that the compound shown in the following table 4 was used instead of the compound a243 in device example 1.
Comparative example 2
An organic electroluminescent element was manufactured in the same manner as in example 1, except that compound HTA was used instead of compound a243 in device example 1.
Test example 2
The organic electroluminescent elements provided in examples 7 to 12 and comparative example 2 were measured for operating voltage (V), current efficiency (c.e.), external Quantum Efficiency (EQE), and color coordinates (CIEx, CIEy) and lifetime at a current density of 10mA/cm 2 by the same test method as in test example 1, and specific performance data are shown in table 4 below.
The current efficiency (c.e.), external Quantum Efficiency (EQE), and color coordinates (CIEx, CIEy) of the organic electroluminescent element were measured by the french FS-100GA4 test, and the lifetime LT97 (the time taken for the initial luminance to decay to 3880nits, referenced to the comparative example, normalized) was measured by the french FS-MP96 test, and all measurements were performed in the room temperature atmosphere.
TABLE 4 Table 4
Compared with comparative example 2, the voltage of the organic electroluminescent element prepared by adopting the spiro compound provided by the application as a hole transport material is reduced, and the efficiency and the service life are obviously improved.
The above description is only of the preferred embodiments of the present invention and is not intended to limit the present invention, but various modifications and variations can be made to the present invention by those skilled in the art. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. A spiro compound, characterized in that the spiro compound has a structure represented by formula (a):
M is selected from formula (I) or formula (II);
Wherein HAr is selected from substituted or unsubstituted C3 to C20 nitrogen containing heteroaryl; ar 1 and Ar 2 are each independently selected from substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C6-C18 heteroaryl; l 1 and L 2 are each independently selected from the group consisting of a direct bond, a substituted or unsubstituted C6-C18 arylene, and a substituted or unsubstituted C6-C18 heteroarylene.
2. The spiro compound according to claim 1, wherein the spiro compound is selected from at least one of the following formulas (a-1) to (a-6):
Wherein HAr, ar 1、Ar2、L1、L2 have the same meaning as in claim 1.
3. The spiro compound according to claim 1, wherein said HAr is selected from substituted or unsubstituted C3 to C12 nitrogen containing heteroaryl groups, preferably substituted or unsubstituted C3 to C8 nitrogen containing heteroaryl groups.
4. The spiro compound according to claim 1, wherein the HAr is selected from at least one of the formulas (HAr-1) to (HAr-10):
Wherein the dashed line represents a bond; z is at least one selected from H, CN, halogen, substituted or unsubstituted C 1～C10 linear alkyl, substituted or unsubstituted C 3～C10 branched alkyl, substituted or unsubstituted C 6～C18 aryl, substituted or unsubstituted C 6～C18 heteroaryl.
5. The spiro compound according to claim 4, wherein Z is selected from at least one of a substituted or unsubstituted C 1～C5 linear alkyl group, a substituted or unsubstituted C 3～C6 branched alkyl group, a substituted or unsubstituted C 6～C12 aryl group, a substituted or unsubstituted C 6～C12 heteroaryl group, preferably at least one of methyl, phenyl, biphenyl, naphthyl, 9' -dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl.
6. The spiro compound according to claim 1, wherein said L 1 and said L 2 are each independently selected from a direct bond or a phenylene group.
7. The spiro compound according to claim 6, wherein the spiro compound is selected from at least one of the following compounds A1 to a 432:
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Preferably, the spiro compound is selected from at least one of compounds a41, a32, a100, a135, a197, a217, a266, a424, a243, a305, a339 or a 385.
8. The use of a spiro compound according to any one of claims 1 to 7 in a hole transporting material or an electron transporting material.
9. An organic electroluminescent element, characterized in that the organic electroluminescent element comprises a substrate layer, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode layer, and the material of the hole transport layer or the electron transport layer comprises the spiro compound according to any one of claims 1 to 7.
10. The organic electroluminescent element according to claim 9, wherein the mass content of the spiro compound in the electron transport layer is 20% to 80%.
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