CN111233677A - Indeno fluoranthene compound and application thereof - Google Patents

Indeno fluoranthene compound and application thereof Download PDF

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CN111233677A
CN111233677A CN202010239755.2A CN202010239755A CN111233677A CN 111233677 A CN111233677 A CN 111233677A CN 202010239755 A CN202010239755 A CN 202010239755A CN 111233677 A CN111233677 A CN 111233677A
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substituted
fluoranthene
compound
unsubstituted
indeno
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梁现丽
段陆萌
范洪涛
李仲庆
杭德余
李继响
班全志
陈婷
曹占广
刘阳
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Beijing Yanhua Jilian Optoelectronic Technology Co ltd
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Beijing Yanhua Jilian Optoelectronic Technology Co ltd
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Abstract

The invention relates to the technical field of organic electroluminescent display, and particularly discloses a novel organic material with an indeno-fluoranthene structure, and also discloses an application of the novel organic material in an organic electroluminescent device. The novel indeno fluoranthene structural compound provided by the invention is shown as a general formula (I)The indeno-fluoranthene structural compound is used as a mother nucleus, and the material has high hole mobility, good film stability, suitable molecular energy level and good thermal stability, can be applied to the field of organic electroluminescence and can be used as a hole transport material. The novel indeno-fluoranthene structural compound provided by the invention can be well applied to OLED devices, and the devices have the advantages of low driving voltage and high luminous efficiency.

Description

Indeno fluoranthene compound and application thereof
Technical Field
The invention relates to the technical field of organic electroluminescent display, in particular to a novel organic material with an indeno-fluoranthene structure, and also relates to application of the novel organic material in an organic electroluminescent device.
Background
The application of the organic electroluminescent (OLED) material in the fields of information display materials, organic optoelectronic materials and the like has great research value and good application prospect. With the development of multimedia information technology, the requirements for the performance of flat panel display devices are higher and higher. The main display technologies at present are plasma display devices, field emission display devices, and organic electroluminescent display devices (OLEDs). The OLED has a series of advantages of self-luminescence, lightness, thinness, power saving, full curing, wide viewing angle, rich colors and the like, compared with a liquid crystal display device, the OLED does not need a backlight source, has wider viewing angle and low power consumption, and has the response speed 1000 times that of the liquid crystal display device, so the OLED has wider application prospect.
At present, blue fluorescence is generally adopted in combination with red and green phosphorescent materials in the organic electroluminescent device structure in the display and illumination field. The light emitting layer of a common electroluminescent device mainly adopts a host-guest doping mode to adjust the light color, the brightness and the efficiency, thereby improving the performance of the device.
At present, more and more display manufacturers are invested in research and development, and the industrialization process of the OLED is greatly promoted. However, the conventional organic electroluminescent materials still have room for improvement in light-emitting properties, and development of new organic electroluminescent materials is urgently needed in the art.
Disclosure of Invention
The invention aims to develop a stable and efficient organic hole transport material which is applied to an OLED device, can reduce the driving voltage and improve the luminous efficiency of the device.
Specifically, the present invention provides an indeno-fluoranthene compound having a structure represented by general formula (i):
Figure BDA0002432162630000011
in the general formula (I), R1～R8In which at least one group is
Figure BDA0002432162630000021
The other groups independently represent hydrogen atom, halogen, straight-chain or branched-chain alkyl, naphthenic base, amino, alkylamino, substituted or unsubstituted aromatic groups containing benzene rings and/or aromatic heterocyclic rings;
the R is9、R10Each independently represents a substituted or unsubstituted aromatic group containing a benzene ring and/or an aromatic heterocyclic ring, and R9、R10May be the same or different;
x, Y are each independently selected from hydrogen atom, halogen, linear or branched alkyl, cycloalkyl, amino, alkylamino, arylamino, substituted or unsubstituted aromatic groups containing a benzene ring and/or aromatic heterocyclic ring;
m and n each independently represent 0, 1 or 2.
As a preferred embodiment of the present invention, said R9、R10Each independently represents a substituted or unsubstituted benzene ring, a substituted or unsubstituted C4-6The heteroaromatic ring, substituted or unsubstituted polyphenyl aliphatic hydrocarbon, substituted or unsubstituted condensed ring aromatic hydrocarbon, substituted or unsubstituted condensed heterocyclic aromatic hydrocarbon, substituted or unsubstituted biaryl hydrocarbon and substituted or unsubstituted spirobifluorene group. When the above groups are substituted, the substituents are preferably: straight or branched alkyl (preferably C)1-4The linear chain or the branched chain alkyl) and the number of the substituent groups is selected from an integer of 1-7.
As a preferred embodiment of the present invention, said R9、R10Each independently represents a substituted or unsubstituted benzene ring, C4-6Heteroaromatic rings, biphenyl, indene, naphthalene, acenaphthylene, fluorene, spirobifluorene, phenanthrene, anthracene, fluoranthene, pyrene, triphenylene, benzo (a) anthracene, benzo (b) fluoranthene, benzo (k) fluoranthene, benzo (a) pyrene, xanthene, acridine, carbazole, dibenzofuran or dibenzothiophene. When the above groups are substituted, the substituents are preferably: c1-4Linear or branched alkyl, C3-6The number of the substituents is selected from an integer of 1-3.
As a preferable mode of the present invention, the above-mentioned
Figure BDA0002432162630000022
In particular selected from the following groups:
Figure BDA0002432162630000023
Figure BDA0002432162630000031
wherein "- -" represents a substituted bit.
As a preferable mode of the present invention, the above-mentioned
Figure BDA0002432162630000032
In particular selected from the following groups:
Figure BDA0002432162630000033
Figure BDA0002432162630000041
as a preferable mode of the present invention, the above-mentioned
Figure BDA0002432162630000042
In particular selected from the following groups:
Figure BDA0002432162630000043
Figure BDA0002432162630000051
in the general formula (I), except for representing
Figure BDA0002432162630000052
And the rest of the groups, besides one, two or more groups, independently represent a hydrogen atom, a halogen, a linear or branched alkyl group (preferably C1-C5), a cycloalkyl group, an amino group, an alkylamino group, a substituted or unsubstituted aromatic group containing a benzene ring and/or an aromatic heterocyclic ring.
As a preferred embodiment of the present invention, said R1～R8In which any one group is
Figure BDA0002432162630000053
As a preferred embodiment of the present invention, said R1～R8In which any two radicals are
Figure BDA0002432162630000054
The two groups may be the same or different.
As a preferred embodiment of the present invention, said R1～R4In which any one group is
Figure BDA0002432162630000055
And said R is5～R8In which any one group is
Figure BDA0002432162630000056
The two groups may be the same or different. Specifically, the R is1And R5Or R1And R7Or R1And R8Or R2And R5Or R2And R6Or R2And R7Or R2And R8Or R3And R5Or R3And R6Or R3And R7Or R3And R8Or R4And R5Or R4And R7Or R4And R8Is composed of
Figure BDA0002432162630000057
The two groups may be the same or different.
As a preferred embodiment of the present invention, said R1～R8In addition to any one, two or more of
Figure BDA0002432162630000058
The rest of the groups (A) and (B) are hydrogen atoms.
In the general formula (I), X, Y is independently selected from hydrogen atom, halogen, straight-chain or branched-chain alkyl (preferably C1-C5), cycloalkyl, amino, alkylamino (preferably C1-C5), substituted or unsubstituted aromatic group containing benzene ring and/or aromatic heterocyclic ring; m and n each independently represent 0, 1 or 2.
In a preferred embodiment of the invention, X represents an arylamine group, a halogen, preferably an F atom, or a linear or branched alkyl group having from C1 to C5, and m is 1 or 2.
In a preferred embodiment of the invention, Y represents an arylamine group, a halogen, preferably an F atom, or a linear or branched alkyl group having from C1 to C5, and n is 1 or 2.
In a preferred embodiment of the invention, X, Y each represents an arylamine group, a halogen, preferably an F atom, or a C1-C5 linear or branched alkyl group, or a hydrogen atom.
As a preferred embodiment of the present invention, the indeno-fluoranthene compound is selected from compounds represented by the following structural formula:
Figure BDA0002432162630000061
Figure BDA0002432162630000071
Figure BDA0002432162630000081
Figure BDA0002432162630000091
Figure BDA0002432162630000101
Figure BDA0002432162630000111
Figure BDA0002432162630000121
Figure BDA0002432162630000131
Figure BDA0002432162630000141
in a second aspect, the invention provides an application of the indeno-fluoranthene compound in preparing an organic electroluminescent device; preferably, the indeno-fluoranthene compound is used as a hole transport material of a hole transport layer in the preparation of an organic electroluminescent device.
In a third aspect, the present invention provides an organic electroluminescent device comprising a hole-transporting layer containing the indeno-fluoranthene compound; preferably, the organic electroluminescent device comprises a transparent substrate, an anode layer, a hole transport layer containing the indeno-fluoranthene compound, an electroluminescent layer, an electron transport layer, an electron injection layer and a cathode layer from bottom to top in sequence.
In a fourth aspect, the present invention provides a display device comprising the organic electroluminescent device.
In a fifth aspect, the present invention provides a lighting apparatus comprising the organic electroluminescent device.
The invention provides a novel indeno-fluoranthene structure compound, the series of compounds take an indeno-fluoranthene structure as a matrix, the matrix structure has a rigid structural unit and good thermal stability, and the structure has proper HOMO and LUMO energy levels and Eg; an electron-donating group with a hole transport property is introduced into an active position of an indeno-fluoranthene compound, namely, an arylamine structure with strong electron-donating capability is introduced into the structure, and an aromatic compound is taken as an end group, so that the novel OLED material with the hole transport property is obtained.
The novel indeno-fluoranthene structural compound provided by the invention takes an indeno-fluoranthene structural compound as a mother nucleus, and the material has high hole mobility, good film stability, suitable molecular energy level and good thermal stability, can be applied to the field of organic electroluminescence and can be used as a hole transport material. The novel indeno-fluoranthene structural compound provided by the invention can be well applied to OLED devices, and the devices have the advantages of low driving voltage and high luminous efficiency. The device can be applied to the field of display or illumination.
Detailed Description
The technical solution of the present invention will be explained in detail below.
According to the preparation method provided by the present invention, a person skilled in the art can use known common means to implement, such as further selecting suitable catalyst and solvent, determining suitable reaction temperature, time, etc., which is not particularly limited by the present invention. The starting materials for the preparation of solvents, catalysts, bases, etc. can be synthesized by published commercial routes or by methods known in the art.
By adopting the preparation method provided by the invention, the invention provides a series of indeno-fluoranthene structural compounds.
Example 1
Figure BDA0002432162630000151
The synthetic route is as follows:
Figure BDA0002432162630000152
the synthesis of the compound I-4 comprises the following specific steps:
A1L three-necked flask was taken, magnetically stirred, and then replaced with nitrogen, followed by addition of potassium tert-butoxide (36.2g, 0.376mol), 3, 4' -dimethyldiphenylamine (41.37g, 0.21mol, purity 99%) and 100ml of toluene in this order. After nitrogen replacement again, (1.2g, 0.006mol) tri-tert-butylphosphine and (0.7g, 0.003mol) palladium acetate were added in this order. After the addition, the temperature was raised to 85 ℃. A solution consisting of (43.41g, 0.1mol, 99 percent purity) M1 and 100ml toluene is added dropwise, the temperature is controlled within the range of 80-120 ℃ for reaction for 4 hours, and the reaction is finished. Adjusting to neutrality, separating organic phase, extracting, drying, column chromatography, and spin-drying solvent to obtain 53.3g pale yellow solid with yield of about 80%.
Product MS (m/e): 666.30, respectively; elemental analysis (C)50H38N2): theoretical value C: 90.06%, H: 5.74%, N: 4.20 percent; found value C: 90.04%, H: 5.75%, N: 4.21 percent.
Example 2
Figure BDA0002432162630000161
The synthetic route is as follows:
Figure BDA0002432162630000162
the synthesis of the compound I-5 comprises the following specific steps:
the 3,4 '-dimethyldiphenylamine and M1 described in example 1 were replaced with N- (1,1' -biphenyl) -3-yl) naphthalen-1-amine and M2, respectively, in equivalent amounts, and the other reaction conditions and operations were the same as in example 1 to obtain 74.23g of a pale yellow solid with a yield of about 86%.
Product MS (m/e): 862.33, respectively; elemental analysis (C)66H42N2): theoretical value C: 91.85%, H: 4.91%, N: 3.25 percent; found value C: 91.83%, H: 4.92%, N: 3.25 percent.
Example 3
Figure BDA0002432162630000171
The synthetic route is as follows:
Figure BDA0002432162630000172
the synthesis of the compound I-21 comprises the following specific steps:
respectively replacing 3, 4' -dimethyldiphenylamine and M1 described in example 1 with N- (naphthyl-2-yl) phenanthroline-9-amine and M3 in equivalent amounts, and performing other reactions under the same conditions and in the same operation as in example 1 to obtain 73.7g of a pale yellow solid with a yield of about 81%.
Product MS (m/e): 910.33, respectively; elemental analysis (C)70H42N2): theory of the inventionThe value C: 92.28%, H: 4.65%, N: 3.07 percent; found value C: 92.26%, H: 4.67%, N: 3.07 percent.
Example 4
Figure BDA0002432162630000173
The synthetic route is as follows:
Figure BDA0002432162630000181
the synthesis of the compound I-25 comprises the following specific steps:
the 3,4 '-dimethyldiphenylamine and M1 described in example 1 were replaced with N- ([1,1' -biphenyl ] -4-yl) anthracen-9-amine and M4, respectively, in equivalent amounts, and the other reaction conditions and operation were the same as in example 1 to give 80.91g of a pale yellow solid with a yield of about 84%.
Product MS (m/e): 962.37, respectively; elemental analysis (C)74H46N2): theoretical value C: 92.28%, H: 4.81%, N: 2.91 percent; found value C: 92.26%, H: 4.82%, N: 2.92 percent.
Example 5
Figure BDA0002432162630000182
The synthetic route is as follows:
Figure BDA0002432162630000183
the synthesis of the compound I-30 comprises the following specific steps:
using N- (9, 9-dimethyl-9H-fluoren-2-yl) triphenyl-2-amine and M5 in a molar ratio of 1.05:1 in place of the 3, 4' -dimethyldiphenylamine and M1 described in example 1, the other reaction conditions and operations were the same as in example 1 to obtain 56.72g of a pale yellow solid with a yield of about 80%.
Product MS (m/e): 709.28, respectively; elemental analysis (C)55H35N): theoretical value C: 93.06%, H: 4.97%, N: 1.97 percent(ii) a Found value C: 93.04%, H: 4.98%, N: 1.98 percent.
Example 6
Figure BDA0002432162630000191
The synthetic route is as follows:
Figure BDA0002432162630000192
the synthesis of the compound I-32 comprises the following specific steps:
using N- ([1,1' -biphenyl ] -4-yl) -9,9' -spirobifluorene ] -2-amine and M6 in a molar ratio of 1.05:1 in place of 3,4 ' -dimethyldiphenylamine and M1 described in example 1, the other reaction conditions and operation were the same as in example 1 to obtain 59.0g of a pale yellow solid in a yield of about 78%.
Product MS (m/e): 757.28, respectively; elemental analysis (C)59H35N): theoretical value C: 93.50%, H: 4.65%, N: 1.85 percent; found value C: 93.51%, H: 4.64%, N: 1.85 percent.
Example 7
Figure BDA0002432162630000193
The synthetic route is as follows:
Figure BDA0002432162630000201
the synthesis of the compound I-38 comprises the following specific steps:
the 3,4 '-dimethyldiphenylamine and M1 described in example 1 were replaced with N- ([ [1,1' -biphenyl ] -4-yl ] dibenzo [ b, d ] furan-3-amine and M7, respectively, in equivalent amounts, and the other reaction conditions and procedures were the same as in example 1, to obtain 74.4g of a pale yellow solid with a yield of about 79%.
Product MS (m/e): 942.32, respectively; elemental analysis (C)70H42N2O2): theoretical value C: 89.15%, H: 4.49%, N: 2.97%, O: 3.39 percent; found value C: 89.14%, H: 4.50%, N: 2.98%, O: 3.38 percent.
Example 8
Figure BDA0002432162630000202
The synthetic route is as follows:
Figure BDA0002432162630000203
the synthesis of the compound I-44 comprises the following specific steps:
the 3, 4' -dimethyldiphenylamine and M1 described in example 1 were replaced with N1, N1-diphenyl-N4- (p-tolyl) benzene-1, 4-diamine and M8 in a molar ratio of 1.05:1, and the other reaction conditions and operations were the same as in example 1 to give 50.54g of a pale yellow solid with a yield of about 81%.
Product MS (m/e): 624.26, respectively; elemental analysis (C)47H32N2): theoretical value C: 90.35%, H: 5.16%, N: 4.48 percent; found value C: 90.33%, H: 5.17%, N: 4.49 percent.
Example 9
Figure BDA0002432162630000211
The synthetic route is as follows:
Figure BDA0002432162630000212
the synthesis of the compound I-58 comprises the following specific steps:
N2under protection, M9(48.1g, 0.1mol), N- (naphthalen-2-yl) naphthalen-1-amine (10.76g, 0.04mol), cuprous chloride (2.97g, 0.03mol), 1, 10-phenanthroline hydrate (3.96g, 0.02mol), potassium hydroxide (16.8g, 0.3mol), and xylene 400mL were added to a 2L three-necked flask equipped with mechanical stirring and a thermometer. Starting stirring, heating to about 80 deg.C to change the system from black to khaki, and heating to 130 deg.C to change the system from khaki to tanA mixture of (21.52g, 0.08mol) N- (naphthalen-2-yl) naphthalen-1-amine and 200mL of xylene was added dropwise. After the addition was complete, the reaction was maintained at reflux (about 138 ℃ C.) for 16 h. Cooling the reaction liquid to 60 ℃, dropwise adding concentrated hydrochloric acid into the reaction liquid for acidification, and stirring for 1h after the dropwise adding is finished. Filtration and spin-drying of the filtrate gave a brownish black oil. Pulping with ethanol, and heating to reflux for 1 hr. Cooling to room temperature, stirring for about 8-10h, filtering, leaching the filter cake with ethanol, and drying to obtain a brown yellow solid. Performing column chromatography by using petroleum ether, and performing spin drying to obtain 44.78g of light yellow solid I-58-1 with the yield of about 72 percent.
Taking a 1L three-necked bottle, stirring with magnetic force, adding potassium tert-butoxide (14.4g, 0.15mol), N- ([ [1,1 '-biphenyl ] -4-yl ] - [1,1' -biphenyl ] -3-amine (32.1g, 0.1mol, purity 99%) and toluene 100ml in sequence after nitrogen displacement, adding (1.2g, 0.006mol) tri-tert-butylphosphine and (0.7g, 0.003mol) palladium acetate in sequence after nitrogen displacement, heating to 85 ℃, beginning to dropwise add a solution consisting of (57.8g, 0.1mol, purity 99%) I-58-1 and 100ml toluene, controlling the temperature to 80-120 ℃ for reaction for 4 hours, adjusting the reaction to neutral after the reaction is finished, separating an organic phase, extracting, drying, and spin-drying the solvent to obtain 64.65g of light yellow solid with the yield of about 75%.
Product MS (m/e): 862.33, respectively; elemental analysis (C)66H42N2): theoretical value C: 91.85%, H: 4.91%, N: 3.25 percent; found value C: 91.84%, H: 4.92%, N: 3.24 percent.
Example 10
Figure BDA0002432162630000221
The synthetic route is as follows:
Figure BDA0002432162630000222
the synthesis of the compound I-65 comprises the following specific steps:
the N- (naphthalen-2-yl) naphthalen-1-amine and M9, N- ([ [1,1 '-biphenyl ] -4-yl ] - [1,1' -biphenyl ] -3-amine and I-58-1 described in example 9 were replaced by N- (naphthalen-1-yl) -9-phenyl-9H-carbazol-2-amine and M10, N- (9, 9-dimethyl-9H-fluoren-2-yl) dibenzo [ b, d ] furan-3-amine and I-65-1, respectively in equiequivalents, and the other reaction conditions and procedures were the same as in example 9 to give 74.23g of a pale yellow solid in about 72% yield.
Product MS (m/e): 1031.39, respectively; elemental analysis (C)77H49N3O): theoretical value C: 89.59%, H: 4.78%, N: 4.07%, O: 1.55 percent; found value C: 89.58%, H: 4.79%, N: 4.06%, O: 1.56 percent.
The intermediates M1 to M10 used in the above examples were all commercially available from Beijing Yanhuaji Union photoelectric technology Co., Ltd.
According to the synthesis schemes of the above examples 1 to 10, other compounds I-1 to I-102 were synthesized by simply replacing the corresponding raw materials without changing any substantial operation.
Example 11
The embodiment provides a group of OLED red light devices, and the structure of the OLED-1 red light device is as follows: ITO/HATCN (1nm)/HT01(40nm)/I-4 compound (20nm)/EML (30nm)/Bphen (40nm)/LiF (1 nm)/Al. Wherein 1nm, 40nm, 20nm, etc. all represent the thickness of the functional layer.
The molecular structure of each functional layer material is as follows:
Figure BDA0002432162630000231
the preparation method comprises the following steps:
(1) carrying out ultrasonic treatment on the glass plate coated with the ITO transparent conductive layer in a commercial cleaning agent, washing the glass plate in deionized water, ultrasonically removing oil in an acetone-ethanol mixed solvent (the volume ratio is 1: 1), baking the glass plate in a clean environment until the water is completely removed, cleaning the glass plate by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
(2) placing the glass substrate with anode in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa, performing vacuum evaporation on the anode layer film to form HATCN as a first hole injection layer, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 1 nm; then, a second hole injection layer HT01 was deposited at a rate of 01nm/s, thickness 40 nm; then evaporating a hole transport layer by using the I-4 compound prepared in the example 1, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 20 nm;
(3) EML is evaporated on the hole transport layer in vacuum and used as a light emitting layer of the device, the EML comprises a main material and a dye material, the evaporation rate of the main material PRH01 is adjusted to be 0.1nm/s by using a multi-source co-evaporation method, and the dye material Ir (piq)2The acac concentration is 5%, and the total film thickness of evaporation plating is 30 nm;
(4) bphen is used as an electron transport material of an electron transport layer of the device, the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 40 nm;
(5) sequentially performing vacuum evaporation on the electron transport layer to form LiF with the thickness of 1nm as an electron injection layer, and forming an Al layer with the thickness of 150nm as a cathode of the device; the OLED-1 red light device is prepared.
According to the same steps as above, only the hole transport layer material in the step (2) is replaced by the compound I-4 prepared in the example 1 respectively by the compound I-5, the compound I-21, the compound I-25, the compound I-30, the compound I-32, the compound I-38, the compound I-44, the compound I-58 and the compound I-65, and the OLED-2 to the OLED-10 red light devices provided by the invention are respectively obtained.
Comparative example OLED-11 provided by the present invention was obtained by following the same procedure as above except that the hole transport layer material in step (2) was replaced with NPB (comparative compound) from the I-4 compound prepared in example 1. The NPB structure is specifically as follows:
Figure BDA0002432162630000241
the performances of the obtained devices OLED-1 to OLED-11 were respectively tested, and the test results are shown in Table 1.
TABLE 1
Figure BDA0002432162630000242
Figure BDA0002432162630000251
As can be seen from the above table, the OLED-1 to OLED-10 prepared by using the organic material shown in the general formula (I) provided by the invention have higher current efficiency than the comparative example OLED-11, and have significantly lower operating voltage than the device OLED-11 using NPB as the hole transport material under the same brightness condition. The organic material shown in the general formula (I) provided by the invention is a novel hole transport material with good performance.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that many modifications and improvements can be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.

Claims (10)

1. An indeno-fluoranthene compound having a structure represented by general formula (i):
Figure FDA0002432162620000011
the R is1～R8In which at least one group is
Figure FDA0002432162620000012
The other groups independently represent hydrogen atom, halogen, straight-chain or branched-chain alkyl, naphthenic base, amino, alkylamino, substituted or unsubstituted aromatic groups containing benzene rings and/or aromatic heterocyclic rings;
the R is9、R10Each independently represents a substituted or unsubstituted aromatic group containing a benzene ring and/or an aromatic heterocyclic ring, and R9、R10May be the same or different;
x, Y are each independently selected from hydrogen atom, halogen, linear or branched alkyl, cycloalkyl, amino, alkylamino, arylamino, substituted or unsubstituted aromatic groups containing a benzene ring and/or aromatic heterocyclic ring;
m and n each independently represent 0, 1 or 2.
2. A compound of claim 1, wherein R is1～R8In which any one group is
Figure FDA0002432162620000013
Or, said R1～R8In which any two radicals are
Figure FDA0002432162620000014
The two groups may be the same or different;
or, said R1～R4In which any one group is
Figure FDA0002432162620000015
And said R is5～R8In which any one group is
Figure FDA0002432162620000016
The two groups may be the same or different.
3. A compound according to claim 1 or 2, wherein R is1～R8In addition to represent
Figure FDA0002432162620000021
In addition to the groups (a), the remaining groups all represent a hydrogen atom.
4. A compound according to any one of claims 1 to 3, wherein R is9、R10Each independently represents a substituted or unsubstituted benzene ring, a substituted or unsubstituted C4-6The heteroaromatic ring, substituted or unsubstituted polyphenyl aliphatic hydrocarbon, substituted or unsubstituted condensed ring aromatic hydrocarbon, substituted or unsubstituted condensed heterocyclic aromatic hydrocarbon, substituted or unsubstituted biaryl hydrocarbon, substituted or unsubstituted spirobifluorene groupClustering;
preferably, said R is9、R10Each independently represents a substituted or unsubstituted benzene ring, C4-6Heteroaromatic rings, biphenyl, indene, naphthalene, acenaphthylene, fluorene, spirobifluorene, phenanthrene, anthracene, fluoranthene, pyrene, triphenylene, benzo (a) anthracene, benzo (b) fluoranthene, benzo (k) fluoranthene, benzo (a) pyrene, xanthene, acridine, carbazole, dibenzofuran or dibenzothiophene.
5. A compound according to any one of claims 1 to 3, wherein the compound is a compound of formula I
Figure FDA0002432162620000022
Selected from:
Figure FDA0002432162620000023
Figure FDA0002432162620000031
wherein "- -" represents a substituted bit.
6. The compound of claim 1, wherein the compound is selected from the group consisting of compounds represented by the following structural formulae:
Figure FDA0002432162620000032
Figure FDA0002432162620000041
Figure FDA0002432162620000051
Figure FDA0002432162620000061
Figure FDA0002432162620000071
Figure FDA0002432162620000081
Figure FDA0002432162620000091
Figure FDA0002432162620000101
Figure FDA0002432162620000111
7. use of an indeno-fluoranthene compound according to any one of claims 1 to 6 for the preparation of an organic electroluminescent device;
preferably, the indeno-fluoranthene compound is used as a hole transport material of a hole transport layer in an organic electroluminescent device.
8. An organic electroluminescent device characterized in that the indeno-fluoranthene compound according to any one of claims 1 to 6 is contained in a hole transport layer of the organic electroluminescent device;
preferably, the organic electroluminescent device comprises a transparent substrate, an anode layer, a hole transport layer containing the indeno-fluoranthene compound according to any one of claims 1 to 6, an electroluminescent layer, an electron transport layer, an electron injection layer and a cathode layer in sequence from bottom to top.
9. A display device comprising the organic electroluminescent element according to claim 8.
10. A lighting device comprising the organic electroluminescent element according to claim 8.
CN202010239755.2A 2020-03-30 2020-03-30 Indeno fluoranthene compound and application thereof Pending CN111233677A (en)

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