CN109956964B - Bipolar organic electroluminescent compound, application thereof and organic electroluminescent device - Google Patents
Bipolar organic electroluminescent compound, application thereof and organic electroluminescent device Download PDFInfo
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- CN109956964B CN109956964B CN201811602621.1A CN201811602621A CN109956964B CN 109956964 B CN109956964 B CN 109956964B CN 201811602621 A CN201811602621 A CN 201811602621A CN 109956964 B CN109956964 B CN 109956964B
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- organic electroluminescent
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- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 description 1
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000007647 flexography Methods 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical compound C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 229960005544 indolocarbazole Drugs 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- JZRYQZJSTWVBBD-UHFFFAOYSA-N pentaporphyrin i Chemical class N1C(C=C2NC(=CC3=NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 JZRYQZJSTWVBBD-UHFFFAOYSA-N 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
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- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
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Abstract
The invention relates to the field of organic electroluminescent devices, and discloses a bipolar organic electroluminescent compound and application thereof, and an organic electroluminescent device, wherein the compound has a structure shown as a formula (I), and X in the formula (I) 1 Is Si or C; x is X 2 Is S or O. The bipolar organic electroluminescent compound provided by the invention can obviously improve the luminous efficiency and prolong the service life of the device when being used in an organic electroluminescent device.
Description
Technical Field
The invention relates to the field of organic electroluminescent devices, in particular to a bipolar organic electroluminescent compound, application of the bipolar organic electroluminescent compound in the organic electroluminescent device and an organic electroluminescent device containing one or more compounds in the bipolar organic electroluminescent compound.
Background
Compared with the traditional liquid crystal technology, the organic electroluminescence (OLED) technology has the characteristics of no need of backlight source irradiation and color filters, capability of emitting light by a pixel per se to be displayed on a color display panel, ultra-high contrast, ultra-wide visible angle, curved surface, thinness and the like.
The performance of an OLED is not only affected by the light emitter, but in particular, the materials forming the various layers of the OLED have a very important influence on the performance of the OLED, such as substrate materials, hole blocking materials, electron transporting materials, hole transporting materials and electron or exciton blocking materials, light emitting materials, etc.
At present, the OLED device still has the defects of high driving voltage, short service life, low current efficiency and low brightness, so that in order to further improve the competitiveness and application field of OLED technology, the optoelectronic performance and the working life of the OLED device are required to be greatly improved, and the OLED device is necessary to be improved as an OLED material with decisive effect on the device performance, so that the development of a high-performance organic electroluminescent material is required to have great significance.
Disclosure of Invention
The invention aims to overcome the defects of low luminous efficiency and short service life of the organic electroluminescent device in the prior art and provides a novel bipolar organic electroluminescent compound which can be remarkably used as the organic electroluminescent device
In order to achieve the above object, a first aspect of the present invention provides a bipolar organic electroluminescent compound having a structure represented by formula (I),
wherein, in the formula (I),
X 1 is Si or C;
X 2 s or O;
R 1 and R is 2 Each independently selected from H, a substituted or unsubstituted nitrogen-containing aromatic hetero-tricyclic, a substituted or unsubstituted nitrogen-containing aromatic hetero-pentacyclic, and R 1 And R is 2 Not simultaneously H;
R 1 and R is 2 The substituents on the substrate are each independently selected from at least one of phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, pyridyl, carbazolyl, and phenyl-substituted carbazolyl.
A second aspect of the invention provides the use of a bipolar organic electroluminescent compound according to the first aspect in an organic electroluminescent device.
A third aspect of the present invention provides an organic electroluminescent device comprising one or more compounds of the bipolar organic electroluminescent compounds according to the first aspect.
The bipolar organic electroluminescent compound provided by the invention can regulate and control the HOMO energy level and the LUMO energy level of the organic electroluminescent material, and can improve the utilization rate of the exciton of the luminescent layer of the organic electroluminescent device, thereby improving the luminous efficiency.
The inventor of the invention discovers in research that the bipolar organic compound provided by the invention has better thermodynamic stability and film forming property, and can obviously reduce the driving voltage and prolong the service life of the device when being used in an organic electroluminescent device.
Detailed Description
No endpoints of the ranges and any values disclosed herein are limited to the precise range or value, and such range or value should be understood to encompass values that are close to the range or value. For numerical ranges, one or more new numerical ranges may be found between the endpoints of each range, between the endpoint of each range and the individual point value, and between the individual point value, and are contemplated as specifically disclosed herein.
As described above, the first aspect of the present invention provides a bipolar organic electroluminescent compound having a structure represented by formula (I),
wherein, in the formula (I),
X 1 is Si or C;
X 2 s or O;
R 1 and R is 2 Each independently selected from H, a substituted or unsubstituted nitrogen-containing aromatic hetero-tricyclic, a substituted or unsubstituted nitrogen-containing aromatic hetero-pentacyclic, and R 1 And R is 2 Not simultaneously H;
R 1 and R is 2 The substituents on the substrate are each independently selected from at least one of phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, pyridyl, carbazolyl, and phenyl-substituted carbazolyl.
According to a preferred embodiment, in formula (I),
the nitrogen-containing heteroaromatic tricyclic ring in the substituted or unsubstituted nitrogen-containing heteroaromatic tricyclic ring is a carbazolyl group shown in formula 1, and the carbazolyl group shown in formula 1 is optionally substituted with at least one group selected from phenyl, biphenyl, pyridyl, carbazolyl and phenyl-substituted carbazolyl groups;
in the above preferred embodiment, the number of substituents which may be contained in the nitrogen-containing aromatic hetero tricyclic ring is not particularly limited, and may be, for example, 1 to 3; the substitution position of the substituent which may be contained in the nitrogen-containing aromatic hetero tricyclic ring is not particularly limited, and may be any position which may be substituted.
According to another preferred embodiment, in the present invention, in formula (I),
the nitrogen-containing heteroaromatic five ring in the substituted or unsubstituted nitrogen-containing heteroaromatic five ring is selected from the group shown in the formulas 2-7, and the group shown in the formulas 2-7 is optionally substituted by at least one group selected from phenyl, biphenyl, pyridyl, carbazolyl and phenyl substituted carbazolyl,
in formula 2-formula 7, X 3 、X 4 、X 5 、X 6 、X 7 And X 8 Each independently selected from
-O-and-S-; wherein R is 11 Is phenyl or biphenyl; r is R 12 And R is 13 Each independently is C 1-10 Alkyl or phenyl of (a);
preferably, the compound of the structure of formula (I) is selected from any one of the following structural formulas:
wherein, in the formulas 1-1, 1-2, 1-3 and 1-4,
R 1 and R is 2 Each independently selected from H, a substituted or unsubstituted nitrogen-containing aromatic hetero-tricyclic, a substituted or unsubstituted nitrogen-containing aromatic hetero-pentacyclic, and R 1 And R is 2 Not simultaneously H;
R 1 and R is 2 The substituents on the polymer are each independently selected from phenyl, biphenyl, dibenzofuranyl, dibenzothienyl, fluorenyl, and picolylAt least one of a pyridyl group, a carbazolyl group and a phenyl-substituted carbazolyl group.
According to a particularly preferred embodiment, in the present invention, the compound of the structure represented by formula (I) is selected from any one of the following compounds:
according to another more preferred embodiment, in order to further improve the light emitting efficiency of the organic light emitting device, in the present invention, the compound of the structure represented by formula (I) is selected from any one of the following compounds:
the specific method for preparing the aforementioned bipolar organic electroluminescent compounds according to the present invention is not particularly limited, and those skilled in the art can obtain the preparation methods of all the bipolar organic electroluminescent compounds according to the specific structural formulae provided in the present invention and the preparation methods of several specific compounds exemplified in the specific examples section of the present invention. The present invention is not specifically exemplified herein for the preparation of all bipolar organic electroluminescent compounds and those skilled in the art are not to be construed as limiting the invention.
As previously mentioned, a second aspect of the present invention provides the use of a bipolar organic electroluminescent compound as described in the first aspect above in an organic electroluminescent device.
As described above, the third aspect of the present invention provides an organic electroluminescent device comprising one or more compounds of the bipolar organic electroluminescent compounds according to the first aspect.
Preferably, the bipolar organic electroluminescent compound is present in at least one of an electron transport layer, a light emitting layer and a hole blocking layer of the organic electroluminescent device.
According to a preferred embodiment, the bipolar organic electroluminescent compound is present in the hole blocking layer of the organic electroluminescent device and acts as a hole blocking material.
According to a preferred embodiment, the organic electroluminescent device comprises a substrate, an anode, a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an optional electron blocking layer, an emissive layer (EML), an optional hole blocking layer, an Electron Transport Layer (ETL), an Electron Injection Layer (EIL) and a cathode, which are stacked in this order.
The substrate of the present invention may use a glass substrate, a plastic substrate, or a metal substrate.
Preferably, the anode material forming the anode is selected from one or more of indium tin oxide, indium zinc oxide and tin dioxide. The anode material may form an anode active layer having a thickness of, for example, 100 to 1700 angstroms.
Preferably, the material forming the hole injection layer is a hole injection material and the material forming the hole transport layer is a hole transport material, and the hole injection material and the hole transport material are selected from aromatic amine derivatives (e.g. NPB, sqMA 1), hexaazabenzophenanthrene derivatives (e.g. HACTN), indolocarbazole derivatives, conductive polymers (e.g. PEDOT/PSS), phthalocyanine or porphine derivatives, dibenzoindenofluorene amine, spirobifluorene amine.
The Hole Injection Layer (HIL) and the Hole Transport Layer (HTL) may be formed using, for example, aromatic amine derivatives of the general formula:
the groups R1 to R9 in the above formula are each independently selected from single bond, hydrogen, deuterium, alkyl, benzene, biphenyl, terphenyl, naphthalene, anthracene, phenanthrene, benzophenanthrene, pyrene, fluorene, dimethylfluorene, spirobifluorene, carbazole, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, indole, indolocarbazole, indenocarbazole, pyridine, pyrimidine, imidazole, thiazole, quinoline, isoquinoline, quinoxaline, quinazoline, porphyrin, carboline, pyrazine, pyridazine or triazine.
Preferably, the hole injection layer has a thickness of 100 to 2000 angstroms, more preferably 200 to 600 angstroms.
Preferably, the hole transport layer has a thickness of 100 to 1000 angstroms, more preferably 200 to 400 angstroms.
Preferably, the material forming the electron transport layer can also be at least one substance selected from the group consisting of metal complexes, benzimidazole derivatives, pyrimidine derivatives, pyridine derivatives, quinoline derivatives, and quinoxaline derivatives. Preferably, the electron transport layer has a thickness of 100 to 600 angstroms.
The material for forming the electron blocking layer is not particularly limited, and in general, compounds capable of having the following condition 1 or/and 2 can be used:
1 st: the light-emitting layer has higher LUMO energy level, and aims to reduce the number of electrons leaving the light-emitting layer, so that the recombination probability of electrons and holes in the light-emitting layer is improved.
2: the device has larger triplet energy, and aims to reduce the number of excitons leaving the light-emitting layer, thereby improving the efficiency of exciton conversion light-emitting.
Materials forming the electron blocking layer include, but are not limited to, aromatic amine derivatives (e.g., NPB), spirobifluorene (e.g., spMA 2), wherein the structures of the partial electron blocking material and the hole injection material and the hole transport material are similar. Preferably the electron blocking layer has a thickness of 50-600 angstroms.
The material forming the hole blocking layer is preferably a compound having the following condition 1 and/or 2:
1 st: the purpose of the high HOMO energy level is to reduce the number of holes leaving the light-emitting layer, so that the recombination probability of electrons and holes in the light-emitting layer is improved.
2: the device has larger triplet energy, and aims to reduce the number of excitons leaving the light-emitting layer, thereby improving the efficiency of exciton conversion light-emitting.
The material forming the hole blocking layer may further contain a phenanthroline derivative (e.g., bphen, BCP), a benzophenanthrene derivative, a benzimidazole derivative, for example. Preferably, the hole blocking layer has a thickness of 50 to 600 angstroms.
Preferably, the electron injection layer material is LiF, al 2 O 3 One or more of MnO, etc. Preferably, the electron injection layer has a thickness of 1 to 50 angstroms.
Preferably, the cathode material is one or more of Al, mg and Ag. Preferably, the thickness of the cathode layer is 800-1500 angstroms.
The organic electroluminescent device according to the invention is preferably coated with a layer or layers by means of a sublimation process. In this case, in a vacuum sublimation system, the temperature is less than 10 -3 Pa, preferably less than 10 -6 The compounds provided herein are applied by vapor deposition at an initial pressure of Pa.
The organic electroluminescent device according to the invention is preferably coated with a layer or layers by means of an organic vapour deposition process or by means of carrier gas sublimation. In this case, at 10 -6 The material is applied at a pressure of Pa to 100 Pa. A particular example of such a process is the organic vapor deposition spray printing process, in whichThe compounds provided by the invention are applied directly through a nozzle and form the device structure.
The organic electroluminescent device of the present invention is preferably formed into one or more layers by photoinitiated thermal imaging or thermal transfer.
The organic electroluminescent device according to the invention is preferably formulated as a solution, and the layer or layers are formed by spin coating or by means of any printing means, such as screen printing, flexography, inkjet printing, lithographic printing, more preferably inkjet printing. However, when a plurality of layers are formed by this method, breakage between layers is liable to occur, that is, when one layer is formed, another layer is formed with a solution, and the formed layer is broken by the solvent in the solution, which is disadvantageous for device fabrication. The compounds provided by the invention can be substituted by structural modification, so that the compounds provided by the invention can be crosslinked under the condition of heating or ultraviolet exposure, thereby maintaining an intact layer without being damaged. The compounds according to the invention can additionally be applied from solution and be crosslinked or immobilized in the corresponding layer by subsequent crosslinking in the polymer network.
Preferably, the organic electroluminescent device of the present invention is manufactured by applying one or more layers from a solution and applying one or more layers by a sublimation method.
Preferred solvents for the preparation of the organic electroluminescent device according to the invention are selected from toluene, anisole, o-xylene, m-xylene, p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, THF, methyl-THF, THP, chlorobenzene, phenoxytoluene, in particular 3-phenoxytoluene, 1,2,3, 5-tetramethylbenzene, 1,2,4, 5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3, 4-dimethylbenzene, 3, 5-dimethylbenzene, acetophenone, benzothiazole, butyl benzoate, isopropanol, cumene, cyclohexanol, cyclohexenone, cyclohexylbenzene, decalin, dodecylbenzene, methyl benzoate, NMP, p-methylisobenzene, phenetole, 1, 4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dibutyl ether, diethylene glycol dibutyl ether, triethylene glycol monobutyl ether, trimethylethanol, 1, 2-dimethylbenzene, 2-hexane, 2-dimethyiheptanol, 1-heptanol, 2-hexane, 2-dimethyibenzene, heptanol, 1-hexane or mixtures thereof.
Preferably, in the preparation of the organic electroluminescent device according to the present invention, the compound according to the present invention and other compounds are thoroughly mixed and then one or more layers are formed by the above-mentioned application means. More preferably, in the vacuum sublimation system, the temperature is less than 10 -3 Pa, preferably less than 10 -6 Each compound is applied by vapor deposition at an initial pressure Pa to form a layer or layers.
The technical scheme of the present invention is described in detail below by specific examples.
The various raw materials used are all commercially available, unless otherwise specified.
Preparation example 1: compounds 1-1-7
Synthesis of intermediate 1-1-7-1: 0.059mol of bis (2-bromophenyl) sulfane was added to 200ml of anhydrous THF and stirred, N 2 Reducing the temperature to-78 ℃ under the protection, dropwise adding 0.118mol of n-butyllithium with the concentration of 2.5mol/L, preserving the temperature for 1 hour at-78 ℃, and then adding 0.059mol of silicon tetrachloride. After the temperature is raised to 25 ℃ and kept for 5 hours, detecting that the reaction of the raw materials is finished, dropwise adding a saturated ammonium chloride aqueous solution into the reaction liquid, stirring for 5 minutes, adding dichlorosilane for extraction, taking an organic phase, drying the organic phase in a spin-drying mode under reduced pressure, and obtaining an intermediate 1-1-7-1 (yield 46%) through column chromatography.
Calculated C12H8Cl2SSi: 283.25.+ -. 1.1H-NMR (400 MHz, CDCl 3) (ppm) delta=7.11 to 7.11 (2H, m), 7.26 to 7.35 (4H, m), 7.51 to 7.52 (2H, m).
Synthesis of intermediate 1-1-7-2: the synthesis method was the same as that of intermediate 1-1-7-1 to give intermediate 1-1-7-2 (yield: 53%).
Calculated C22H14N2SSi: 366.51.+ -. 1.1H-NMR (400 MHz, CDCl) 3 )(ppm) δ＝7.11～7.11(2H，m)，7.24～7.35(6H，m)，7.51～7.52(2H，m)，7.93～7.94 (2H，m)，8.63～8.64(2H，m)。
Synthesis of intermediate 1-1-7-3: 0.0143mol of intermediate 1-1-7-2 was added to 53ml of DMF and stirred, the temperature was controlled at 0℃and 0.0286mol of NBS was added, the temperature was raised to 50℃and after 4 hours of reaction, the reaction was completed, 100ml of water was added to the reaction mixture to precipitate a solid and the solid was filtered to obtain a product, and the residue was subjected to column chromatography to obtain intermediate 1-1-7-3 (yield 45%).
Calculated C22H12Br2N2SSi: 524.30.+ -. 1.1H-NMR (400 MHz, CDCl 3) (ppm) delta=7.24-7.26 (2H, m), 7.40-7.41 (2H, m), 7.51-7.52 (2H, m), 7.81-7.82 (2H, m), 7.94-7.95 (2H, m), 8.63-8.64 (2H, m).
Synthesis of Compounds 1-1-7: 6.4mmol of intermediate 1-1-7-3 is dissolved in 20ml of toluene solvent, stirred under nitrogen, 0.0128mol of 7, 7-dimethyl-5, 7-indano [2,1-b ] carbazole, 0.03mol of sodium tert-butoxide, 0.06mmol of tris (dibenzylideneacetone) dipalladium and 0.06mmol of tri-tert-butylphosphine are added in sequence, the reaction is carried out for 8h, the detection is carried out after the reaction, the reaction is finished, the reaction is stopped, the reaction solution is dried under reduced pressure, and the obtained residue is recrystallized by xylene to obtain the compound 1-1-7 (yield 61%).
Calculated C64H44N4SSi: 929.21.+ -. 1.1H-NMR (400 MHz, CDCl 3) (ppm) delta=1.72-1.72 (12H, s), 7.24-7.29 (6H, m), 7.44-7.52 (10H, m), 7.61-7.69 (6H, m), 7.93-7.94 (2H, m), 8.09-8.12 (4H, m), 8.39-8.39 (2H, s), 8.62-8.63 (2H, m).
Preparation example 2: compounds 1-1-12
Synthesis of intermediate 1-1-12-1 by adding 0.0076mol of intermediate 1-1-7-2 into 30ml of DMF, stirring, controlling the temperature to 0 ℃, adding 0.0076mol of NBS, heating to 50 ℃, detecting the reaction completion of the raw materials after 4 hours of reaction, adding 150ml of water into the reaction solution, precipitating solid, filtering to obtain a product, and obtaining intermediate 1-1-12-1 (yield 48%) from the residue through column chromatography.
Calculated C22H13Br2N2Ssi: 445.41.+ -. 1.1H-NMR (400 MHz, CDCl 3) (ppm) delta=7.11-7.13 (1H, m), 7.24-7.51 (5H, m), 7.51-7.52 (2H, m), 7.81-7.82 (1H, m), 7.94-7.95 (2H, m), 8.63-8.64 (2H, m).
Synthesis of Compounds 1-1-12: the synthesis method was the same as that of compound 1-1-7 to give compound 1-1-12 (yield 63%).
Calculated C46H28N4Ssi: 696.18.+ -. 1.1H-NMR (400 MHz, CDCl 3) (ppm) delta=7.07-7.22 (9H, m), 7.31-7.35 (1H, m), 7.44-7.53 (6H, m), 7.57-7.64 (6H, m), 7.93-7.95 (2H, m), 8.48-8.51 (2H, m), 8.53-8.56 (2H, m).
Preparation example 3: compounds 1-2-7
Synthesis of intermediate 1-2-7-1: the synthesis method is the same as that of the intermediate 1-1-7-1, and the intermediate 1-2-7-1 is obtained (yield: 53%).
Calculated C12H8Cl2Osi: 267.18.+ -. 1.1H-NMR (400 MHz, CDCl 3) (ppm) delta=7.09-7.10 (2H, m), 7.24-7.25 (2H, m), 7.42-7.51 (4H, m).
Synthesis of intermediate 1-2-7-2: the synthesis method is the same as that of the intermediate 1-1-7-1, and the intermediate 1-2-7-2 is obtained (yield 49%).
Calculated C22H14N2OSi: 350.44.+ -. 1.1H-NMR (400 MHz, CDCl 3) (ppm) delta=7.09-7.09 (2H, m), 7.24-7.26 (4H, m), 7.42-7.51 (4H, m), 7.93-7.94 (2H, m), 8.63-8.64 (2H, m).
Synthesis of intermediate 1-2-7-3: the synthesis method is the same as that of the intermediate 1-1-7-3, and the intermediate 1-2-7-3 is obtained (yield 52%).
Calculated C22H12Br2N2OSi: 508.24.+ -. 1.1H-NMR (400 MHz, CDCl 3) (ppm) delta=7.13-7.14 (2H, m), 7.24-7.26 (2H, m), 7.66-7.67 (4H, m), 7.93-7.94 (2H, m), 8.63-8.64 (2H, m).
Synthesis of Compounds 1-2-7: the synthesis method is the same as that of the intermediate 1-1-7, and the compound 1-2-7 is obtained (yield 55%).
Preparation example 4: compounds 1-2-16
Synthesis of intermediate 1-2-16-1: 0.0096mol of intermediate 1-2-7-2 is added into 30ml of DMF, the temperature is controlled to be 0 ℃, 0.0091mol of NBS is added, the temperature is raised to be 50 ℃, after the reaction is carried out for 4 hours, the reaction is detected to be finished, 150ml of water is added into the reaction solution, solid precipitation is filtered, and the product is obtained, and the residue is subjected to column chromatography to obtain intermediate 1-2-16-1 (yield 48%).
Calculated C22H13BrN2OSi: 429.34.+ -. 1.1H-NMR (400 MHz, CDCl 3) (ppm) delta=7.09-7.13 (2H, m), 7, 24-7.26 (3H, m), 7.42-7.51 (2H, m), 7.66-7.67 (2H, m), 7.94-7.96 (2H, m), 8.63-8.65 (2H, m).
Synthesis of Compounds 1-2-16: the synthesis method is the same as that of the compound 1-1-7, and the compound 1-2-16 is obtained (yield 58%).
Calculated C43H29N3OSi: 631.80.+ -. 1.1H-NMR (400 MHz, CDCl 3) (ppm) delta=1.72-1.72 (6H, s), 7.09-7.11 (1H, m), 7..24-7.33 (8H, m), 7.42-7.51 (3H, m), 7.61-7.69 (4H, m), 7.94-7.96 (3H, m), 8.09-8.11 (1H, m), 8.55-8.57 (1H, m), 8.63-8.65 (2H, m).
Preparation example 5: compounds 1-3-1
Synthesis of intermediate 1-3-1-1: 1-chloro-2-phenylsulfanylbenzene (0.05 mol) was added to a three-necked flask under a nitrogen atmosphere, followed by addition of 110ml of anhydrous tetrahydrofuran. After stirring at-78℃for 10min, 2.4M n-butyllithium (0.055 mol) was added dropwise via a constant pressure dropping funnel. After 1h of reaction, an anhydrous tetrahydrofuran solution (200 mL) dissolved with 4, 5-diazafluoren-9-one (0.05 mol) was slowly added dropwise, the temperature was naturally raised to 25℃overnight after 1h of reaction, and after the completion of the reaction, 25mL of water was added dropwise to quench the reaction. The solvent was removed, dichloromethane was extracted with water, the organic phase was taken and the dichloromethane was evaporated to dryness to give 17.52g of yellow solid which was taken directly to the next reaction without any treatment.
Calculated C23H14N2S: 350.44.+ -. 1.1H-NMR (400 MHz, CDCl 3) (ppm) delta=6.81-6.81 (2H, m), 7.03-7.07 (4H, m), 7.33-7.33 (2H, m), 7.48-7.48 (2H, m), 7.65-7.65 (2H, m), 8.51-8.51 (2H, m).
Synthesis of intermediate 1-3-1-2: dissolving 0.05mol of intermediate 1-3-1-1 in 180ml of N, N-dimethylformamide, heating to 50 ℃, dropwise adding 150ml of NBS dissolved in N, N-dimethylformamide, heating to 100 ℃ after the dropwise adding is finished, stirring for 2 hours, detecting that raw materials react, cooling to room temperature, dropwise adding 300ml of water, stirring for 20 minutes, filtering, and drying to obtain intermediate 1-3-1-2 (yield 50%).
Calculated C23H12Br2N2S: 508.23.+ -. 1.1H-NMR (400 MHz, CDCl 3) (ppm) delta=6.81-6.81 (2H, m), 7.18-7.18 (4H, m), 7.48-7.52 (4H, s), 8.51-8.51 (2H, m).
Synthesis of Compound 1-3-1 by dissolving 0.025mol of intermediate 1-3-1-2 in 130ml of toluene solvent, stirring under nitrogen, then sequentially adding 0.05mol of carbazole, 0.075mol of sodium tert-butoxide, 0.0025mol of dibenzylideneacetone dipalladium, and 0.0025mol of tri-tert-butylphosphine, heating to reflux reaction, detecting the reaction completion of raw materials after 6 hours, drying the reaction solution under reduced pressure, and obtaining Compound 1-3-1 by column chromatography (yield 55%).
Calculated C47H28N4S: 680.82.+ -. 1.1H-NMR (400 MHz, CDCl 3) (ppm) delta=6.81-6.81 (2H, m), 7.23-7.36 (12H, m), 7.48-7.50 (4H, m), 7.63-7.63 (2H, m), 7.94-7.94 (2H, m), 8.12-8.12 (2H, m), 8.51-8.55 (4H, m).
Preparation example 6: compounds 1-3-2
Synthesis of Compound 1-3-2 the same procedure as for Compound 1-3-1 gave Compound 1-3-2 (yield 58%).
Calculated C59H36N4S: 833.01.+ -. 1.1H-NMR (400 MHz, CDCl 3) (ppm) delta=6.81-6.82 (2H, m), 7.23-7.52 (22H, m) 7.62-7.64 (2H, d), 7.79-7.81 (2H, m), 7.94-7.96 (2H, m), 8.18-8.20 (2H, d), 8.51-8.55 (4H, m).
Preparation example 7: compounds 1-3-12
Synthesis of intermediate 1-3-12-1: the synthesis method was identical to intermediate 1-3-1-2 to give intermediate 1-3-12-1 (yield 59%).
Calculated C23H13BrN2S: 429.33.+ -. 1.1H-NMR (400 MHz, CDCl 3) (ppm) delta=6.81-6.83 (2H, m), 7.03-7.07 (2H, m), 7.18-7.20 (2H, m), 7.33-7.33 (1H, m), 7.48-7.52 (3H, m), 7.65-7.65 (1H, m), 8.51-8.53 (2H, m).
Synthesis of Compound 1-3-12 the same procedure as for Compound 1-3-1 gave Compound 1-3-12 (yield 58%).
Calculated C47H28N4S: 680.82.+ -. 1.1H-NMR (400 MHz, CDCl 3) (ppm) delta=6.81-6.81 (2H, m), 7.03-7.07 (2H, m), 7.25-7.65 (19H, m), 7.94 (1H, m), 8.12 (1H, m), 8.51-8.55 (3H, m)
Preparation example 8: compounds 1-4-1
Synthesis of intermediate 1-4-1-1: under nitrogen atmosphere, 0.0977mol of 2-chlorodiphenyl ether was added to a three-necked flask, and 200ml of anhydrous tetrahydrofuran was added. After stirring for 10min at-78℃2.4M n-butyllithium (0.1192 mol) was added dropwise from a constant pressure dropping funnel. After 1h of reaction, an anhydrous tetrahydrofuran solution (50 mL) dissolved with 4, 5-diazafluorene-9-ketone (0.0294 mol) was slowly added dropwise, and after 1h of reaction, the temperature was naturally raised to 25 ℃ overnight, and after the reaction was completed, 5mL of water was added dropwise for quenching reaction. The solvent was removed, dichloromethane was extracted with water, the organic phase was taken and the dichloromethane was evaporated to dryness to give 22.4g of yellow solid which was taken directly to the next reaction without any work-up.
Calculated C23H14N2O: 334.37.+ -. 1.1H-NMR (400 MHz, CDCl 3) (ppm) δ=6.81 (2H, m), 7.05 (2H, m), 7.19-7.22 (6H, m), 7.48 (2H, m), 8.51 (2H, m).
The synthesis of intermediate 1-4-1-2 comprises dissolving 0.0670mol of intermediate 1-4-1-1 in 220ml of N, N-dimethylformamide, heating to 50deg.C, dropwise adding 0.1340mol of NBS dissolved in 150ml of N, N-dimethylformamide, heating to 100deg.C after dropwise adding, stirring for 2h, detecting that the raw materials are reacted, cooling the reaction solution to 25deg.C, dropwise adding 900ml of water, stirring for 20min, filtering, and oven drying to obtain intermediate 1-4-1-2 (yield 58%).
Calculated C23H12Br2N2O: 492.16.+ -. 1.1H-NMR (400 MHz, CDCl 3) (ppm) δ=6.81 (2H, m), 7.35 (2H, m), 7.48 (2H, m), 7.63 (2H, m), 8.51 (2H, m).
Synthesis of Compound 1-4-1: 0.0389mol of intermediate 1-4-1-2 is dissolved in 200ml of toluene, stirring is carried out under nitrogen, 0.0778mol of carbazole, 0.0973mol of sodium tert-butoxide, 0.10g of tris (dibenzylideneacetone) dipalladium and 0.26ml of tri-tert-butylphosphine are sequentially added, the temperature is raised to reflux, after 4 hours, HPLC detection is carried out, the raw materials are basically reacted, the reaction solution is dried under reduced pressure, and the residue is subjected to column chromatography to obtain the compound 1-4-1 (yield: 60%).
Calculated C47H28N4O: 664.75.+ -. 1.1H-NMR (400 MHz, CDCl 3) (ppm) delta=6.81 (2H, m), 7.02 (2H, m), 7.25-7.50 (14H, m), 7.63 (2H, m), 7.94 (2H, m), 8.12 (2H, m), 8.51-8.55 (4H, m).
Example 1: preparation of organic light-emitting device
After a glass substrate having an Indium Tin Oxide (ITO) electrode (first electrode, anode) with a thickness of about 1500 angstroms was sequentially ultrasonically washed with distilled water and methanol, the washed glass substrate was dried, moved to a plasma cleaning system, and then cleaned using oxygen plasma for about 5 minutes. The glass substrate is then loaded into a vacuum deposition apparatus.
Vacuum depositing HAT-CN onto the ITO electrode of the glass substrate to form HIL having a thickness of about 100 angstroms; the TAPC was vacuum deposited onto the hole injection layer to form an HTL having a thickness of about 400 angstroms.
DMIC-TRZ and Ir (ppy) 3 Co-deposition on the cavity transport region at a vacuum deposition rate ratio of 97:3 to form an EML having a thickness of about 300 angstroms.
Compound 1-1-1 was vacuum deposited onto the light emitting layer to form an HBL having a thickness of about 50 angstroms.
Subsequently, compound LG201 was vacuum deposited on the EML to form an ETL having a thickness of about 250 angstroms. Then, liF is deposited on the ETL to form an EIL having a thickness of about 5 angstroms, and Al is deposited on the EIL to a thickness of about 1000 angstroms to form a second electrode (cathode), thereby completing the fabrication of the organic light emitting device.
Other embodiments
An organic light-emitting device of the remaining examples was prepared by a similar method to example 1, except that the compounds 1-1-1 of example 1 were replaced with the compounds shown in table 1.
Comparative example 1
An organic light-emitting device was produced by a method similar to that in example 1, except that TPBi was used instead of the compound 1-1-1 in example 1.
Evaluation: evaluation of characteristics of organic light-emitting device
The driving voltages, emission efficiencies and lifetimes of the organic light emitting devices in examples and comparative examples were measured using a current-voltage source meter (Keithley 2400) and a Minolta CS-1000A spectroradiometer. The results are shown in table 1 below.
(1) Measurement of current density variation with respect to voltage variation
The current value flowing through each of the organic light emitting devices was measured while increasing the voltage from 0 volt (V) to about 10V by using a current-voltage source meter (Keithley 2400) and then divided by the area of the corresponding light emitting device to obtain a current density.
(2) Measurement of brightness change relative to voltage change
The brightness of the organic light emitting device was measured by using a Minolta CS-1000A spectroradiometer while increasing the voltage from about 0V to about 10V.
(3) Measurement of current efficiency
The organic light emitting device was calculated at 20 milliamp/square centimeter (mA/cm) based on the current density, voltage and brightness obtained by the above-described measurements (1) and (2) 2 ) Is provided.
(4) Measurement of lifetime
Keep 10000cd/m 2 Is (cd/m) 2 ) And the time for which the current efficiency (cd/a) was reduced to 80% was measured.
TABLE 1
| Examples | HBT | Driving voltage (V) | Efficiency (cd/A) | T80(hrs) |
| Example 1 | 1-1-1 | 4.06 | 71.4 | 174 |
| Example 2 | 1-1-12 | 4.02 | 72.2 | 171 |
| Example 3 | 1-1-17 | 3.75 | 69.4 | 165 |
| Example 4 | 1-2-1 | 3.93 | 71 | 173 |
| Example 5 | 1-2-2 | 4.04 | 68.4 | 168 |
| Example 6 | 1-2-5 | 3.83 | 72.6 | 175 |
| Example 7 | 1-3-1 | 3.92 | 74.1 | 176 |
| Example 8 | 1-3-2 | 4.21 | 62.7 | 162 |
| Example 9 | 1-3-12 | 3.68 | 72.5 | 164 |
| Example 10 | 1-4-1 | 3.91 | 70.2 | 167 |
| Example 11 | 1-4-2 | 4.13 | 63.5 | 163 |
| Example 12 | 1-4-5 | 3.77 | 70.5 | 162 |
| Example 13 | 1-4-7 | 3.51 | 72.2 | 169 |
| Example 14 | 1-4-8 | 3.81 | 69.8 | 170 |
| Example 15 | 1-4-10 | 4.03 | 67.9 | 162 |
| Example 16 | 1-4-14 | 3.87 | 71.9 | 162 |
| Comparative example | TPBi | 4.7 | 58.2 | 134 |
The organic electroluminescent device formed by the novel compound of the present invention has a low driving voltage and remarkably higher lifetime, current efficiency and brightness than those of the prior art.
The preferred embodiments of the present invention have been described in detail above, but the present invention is not limited thereto. Within the scope of the technical idea of the invention, a number of simple variants of the technical solution of the invention are possible, including that the individual technical features are combined in any other suitable way, which simple variants and combinations should likewise be regarded as being disclosed by the invention, all falling within the scope of protection of the invention.
Claims (7)
1. A bipolar organic electroluminescent compound having a structure represented by formula (I),
wherein, in the formula (I),
X 1 is Si or C;
X 2 s or O;
R 1 and R is 2 Each independently selected from H, a substituted or unsubstituted nitrogen-containing aromatic hetero-tricyclic, a substituted or unsubstituted nitrogen-containing aromatic hetero-pentacyclic, and R 1 And R is 2 Not simultaneously H;
the nitrogen-containing heteroaromatic tricyclic ring in the substituted or unsubstituted nitrogen-containing heteroaromatic tricyclic ring is a carbazolyl group shown in formula 1, and the carbazolyl group shown in formula 1 is optionally substituted by phenyl;
the nitrogen-containing heteroaromatic pentacyclic ring in the substituted or unsubstituted nitrogen-containing heteroaromatic pentacyclic ring is selected from the group shown in formula 2, formula 4, formula 5 and formula 6,
in the formulae 2,4 to 6, X 3 、X 5 、X 6 、X 7 Each independently selected from
-O-and-S-; wherein R is 11 Is phenyl; r is R 12 And R is 13 Each independently is methyl; />
R 1 And R is 2 The substituents on each are independently selected from phenyl.
2. The bipolar organic electroluminescent compound according to claim 1, wherein the compound of formula (I) is selected from any one of the following structural formulas:
wherein, in the formulas 1-1, 1-2, 1-3 and 1-4,
R 1 and R is 2 Each independently selected from H, a substituted or unsubstituted nitrogen-containing aromatic hetero-tricyclic, a substituted or unsubstituted nitrogen-containing aromatic hetero-pentacyclic, and R 1 And R is 2 Not simultaneously H;
the nitrogen-containing heteroaromatic tricyclic ring in the substituted or unsubstituted nitrogen-containing heteroaromatic tricyclic ring is a carbazolyl group shown in formula 1, and the carbazolyl group shown in formula 1 is optionally substituted by phenyl;
the nitrogen-containing heteroaromatic pentacyclic in the substituted or unsubstituted nitrogen-containing heteroaromatic pentacyclic is selected from the group shown in formula 2, formula 4, formula 5 and formula 6, wherein X is in formula 2, formula 4 to formula 6 3 、X 5 、X 6 、X 7 Each independently selected from
-O-and-S-; wherein R is 11 Is phenyl; r is R 12 And R is 13 Each independently is methyl;
R 1 and R is 2 The substituents on each are independently selected from phenyl.
3. The bipolar organic electroluminescent compound according to claim 1, wherein the compound of the structure represented by formula (I) is selected from any one of the following compounds:
4. the bipolar organic electroluminescent compound according to claim 3, wherein the compound of the structure represented by formula (I) is selected from any one of the following compounds:
5. use of the bipolar organic electroluminescent compound as claimed in any of claims 1-4 in an organic electroluminescent device; the bipolar organic electroluminescent compound is present in a hole blocking layer of the organic electroluminescent device.
6. An organic electroluminescent device comprising one or more compounds of the bipolar organic electroluminescent compounds as claimed in any one of claims 1 to 4;
the bipolar organic electroluminescent compound is present in a hole blocking layer of the organic electroluminescent device and acts as a hole blocking material.
7. The organic electroluminescent device of claim 6, wherein the organic electroluminescent device comprises a substrate, an anode, a hole injection layer, a hole transport layer, an optional electron blocking layer, a light emitting layer, an optional hole blocking layer, an electron transport layer, an electron injection layer, and a cathode, which are sequentially stacked.
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| CN111518109B (en) * | 2019-02-01 | 2021-10-01 | 北京绿人科技有限责任公司 | Organic compound, application thereof and organic electroluminescent device |
| KR102695222B1 (en) | 2019-07-17 | 2024-08-13 | 엘지디스플레이 주식회사 | Organic compounds having improved luminsecent properties, organic light emitting diode and organic light emitting device including the compounds |
| CN111039800B (en) * | 2019-11-05 | 2022-11-04 | 北京绿人科技有限责任公司 | Organic compound containing condensed ring structure and organic electroluminescent device |
| CN115490624B (en) * | 2021-06-18 | 2024-09-03 | 北京绿人科技有限责任公司 | Azetidine-containing organic compound and organic electroluminescent device |
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