CN110903294A - Compound with benzo [1,2-b:5, 4-b' ] dibenzofuran as core and application thereof - Google Patents

Compound with benzo [1,2-b:5, 4-b' ] dibenzofuran as core and application thereof Download PDF

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CN110903294A
CN110903294A CN201811086670.4A CN201811086670A CN110903294A CN 110903294 A CN110903294 A CN 110903294A CN 201811086670 A CN201811086670 A CN 201811086670A CN 110903294 A CN110903294 A CN 110903294A
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李崇
唐丹丹
谢丹丹
张兆超
赵四杰
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Jiangsu Sunera Technology Co Ltd
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Abstract

The invention discloses a compound taking benzo [1,2-b:5, 4-b' ] dibenzofuran as a core and application thereof. The compound contains a benzo [1,2-b:5, 4-b' ] dibenzofuran structure, has strong rigidity, and has the characteristics of difficult crystallization and aggregation among molecules and good film forming property after connecting a five-membered ring union ring or a six-membered ring union ring or a seven-membered ring union ring; the compound has different electron-donating abilities of the branched chain structures, so that the HOMO energy levels of the material are different, and the material can be used as materials of different functional layers; in addition, the compound has higher triplet state energy level, can effectively block energy loss and is beneficial to energy transfer. Therefore, after the compound is used as an organic electroluminescent functional layer material to be applied to an OLED device, the efficiency and the service life of the device are greatly improved.

Description

Compound with benzo [1,2-b:5, 4-b' ] dibenzofuran as core and application thereof
Technical Field
The invention relates to a compound taking benzo [1,2-b:5, 4-b' ] dibenzofuran as a core and application thereof in an organic electroluminescent device, belonging to the technical field of semiconductors.
Background
Currently, the OLED display technology is already applied in the fields of smart phones, tablet computers, and the like, and is further expanded to the large-size application field of televisions, and the like, but compared with the actual product application requirements, the performance of the OLED device, such as light emitting efficiency, service life, and the like, needs to be further improved. Current research into improving the performance of OLED light emitting devices includes: the driving voltage of the device is reduced, the luminous efficiency of the device is improved, the service life of the device is prolonged, and the like. In order to realize the continuous improvement of the performance of the OLED device, not only the innovation of the structure and the manufacturing process of the OLED device but also the continuous research and innovation of the photoelectric functional material of the OLED are required to create the functional material of the OLED with higher performance.
The photoelectric functional materials of the OLED applied to the OLED device can be divided into two categories from the aspect of application, namely charge injection transmission materials and luminescent materials. Further, the charge injection transport material may be classified into an electron injection transport material, an electron blocking material, a hole injection transport material, and a hole blocking material, and the light emitting material may be classified into a host light emitting material and a doping material.
In order to fabricate a high-performance OLED light-emitting device, various organic functional materials are required to have good photoelectric properties, for example, as a charge transport material, good carrier mobility, high glass transition temperature, etc. are required, as a host material of a light-emitting layer, good bipolar, appropriate HOMO/LUMO energy level, etc. are required.
The OLED photoelectric functional material film layer for forming the OLED device at least comprises more than two layers of structures, the OLED device structure applied in industry comprises a hole injection layer, a hole transmission layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transmission layer, an electron injection layer and other various film layers, namely the photoelectric functional material applied to the OLED device at least comprises a hole injection material, a hole transmission material, a light emitting material, an electron transmission material and the like, and the material type and the matching form have the characteristics of richness and diversity. In addition, for the collocation of OLED devices with different structures, the used photoelectric functional material has stronger selectivity, and the performance of the same material in the devices with different structures can be completely different.
Therefore, aiming at the industrial application requirements of the current OLED device and the requirements of different functional film layers and photoelectric characteristics of the OLED device, a more suitable OLED functional material or material combination with higher performance needs to be selected to realize the comprehensive characteristics of high efficiency, long service life and low voltage of the device. In terms of the actual demand of the current OLED display lighting industry, the development of the current OLED material is far from enough, and lags behind the requirements of panel manufacturing enterprises, and it is very important to develop a higher-performance organic functional material as a material enterprise.
Disclosure of Invention
In view of the above, the present invention aims to provide a compound having benzo [1,2-b:5, 4-b' ] dibenzofuran as a core and use thereof. The compound takes benzo [1,2-b:5, 4-b' ] dibenzofuran as a core, has higher glass transition temperature and molecular thermal stability, proper HOMO and LUMO energy levels and higher Eg, and can be used as a hole transport layer/electron blocking layer material or a light-emitting layer material of an organic electroluminescent device through device structure optimization, so that the photoelectric property of the OLED device and the service life of the OLED device are effectively improved.
The technical scheme for solving the technical problems is as follows: a compound taking benzo [1,2-b:5, 4-b' ] dibenzofuran as a core, wherein the structure of the compound is shown as a general formula (1):
Figure BDA0001803318480000021
in the general formula (1), L represents a single bond, a substituted or unsubstituted C6-30 arylene group, a substituted or unsubstituted 5-to 30-membered heteroarylene group containing one or more hetero atoms;
in the general formula (1), R represents a structure shown in a general formula (2);
Figure BDA0001803318480000022
in the general formula (2), in the formula,R1、R2each independently represents a hydrogen atom, a structure represented by general formula (3) or general formula (4); r1 is the same or different from R2; r1And R2Not being hydrogen atoms at the same time;
Figure BDA0001803318480000023
in the general formulae (2) and (4), X1, X2, and X3 each independently represents a single bond, an oxygen atom, a sulfur atom, -CR3 ═ CR4 —, and,
Figure BDA0001803318480000024
-one of C (R5) (R6) -, -Si (R7) (R8) -or-N (R9) -;
r3 to R9 each independently represent one of a hydrogen atom, a C1-20 linear alkyl group, a C3-20 branched alkyl group, a C1-20 linear alkyl substituted silane group, a C3-20 branched alkyl substituted silane group, a substituted or unsubstituted C6-30 aryl group, a substituted or unsubstituted 5-to 30-membered heteroaryl group containing one or more heteroatoms; r3 and R4, R5 and R6 may also be bonded to each other to form a 5-to 30-membered aliphatic, aromatic or heteroaromatic ring;
the substituent is selected from one or more of halogen, cyano, C6-30 aryl and 5-to 30-membered heteroaryl containing one or more heteroatoms; the heteroatom is selected from an oxygen atom, a sulfur atom or a nitrogen atom.
On the basis of the technical scheme, the invention can be further improved as follows.
Further, in the general formula (1), L represents a single bond (L-1) in the general formula (1),
Figure BDA0001803318480000031
Figure BDA0001803318480000032
Wherein Z in L-2 to L-20, identically or differently at each occurrence, is denoted C-R10 or N; the R10 represents hydrogen atom, halogen, cyano, C1-20 alkyl, substituted or not at each occurrenceOr one of an unsubstituted C6-30 aryl group, a substituted or unsubstituted 5-to 30-membered heteroaryl group containing one or more heteroatoms; two or more adjacent R10 may be bonded to each other to form a ring; and
Figure BDA0001803318480000033
and Z to which R is bonded is C.
Further, in the general formula (1), L represents any one of L-1 to L-20; wherein Z in L-2 to L-20, identically or differently at each occurrence, is denoted C-R10 or N; r10 represents, identically or differently at each occurrence, one of a hydrogen atom, halogen, cyano, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, phenyl, tolyl, xylyl, trimethylphenyl, isopropylphenyl, tert-butylphenyl, biphenyl, naphthyl, pyridyl, pyridazinyl, pyrazinyl, pyrimidinyl, triazinyl, dibenzofuranyl, cyanophenyl or carbazolyl; two or more adjacent R10 may be bonded to each other to form a ring; and
Figure BDA0001803318480000041
and R is bonded Z is C;
further, the general formula (2) is represented by
Figure BDA0001803318480000042
Figure BDA0001803318480000051
Figure BDA0001803318480000061
Figure BDA0001803318480000071
Figure BDA0001803318480000081
Figure BDA0001803318480000091
Figure BDA0001803318480000101
Figure BDA0001803318480000111
Figure BDA0001803318480000121
Figure BDA0001803318480000131
Figure BDA0001803318480000141
Figure BDA0001803318480000142
Any one of the above;
wherein Y, which may be the same or different, represents an oxygen atom, a sulfur atom, -CR11＝CR12-、
Figure BDA0001803318480000143
-one of C (R13) (R14) -, -Si (R15) (R16) -or-N (R17) -;
R11-R17 are respectively and independently one of hydrogen atom, C1-10 linear alkyl, C3-10 branched alkyl, C1-10 linear alkyl substituted silane, C3-10 branched alkyl substituted silane, substituted or unsubstituted C6-20 aryl and substituted or unsubstituted 5-30-membered heteroaryl containing one or more heteroatoms.
Further, the general formula (2) is independently represented by any one of A-1 to A-693; wherein, Y is the same or different and represents one of an oxygen atom, a sulfur atom, -CR11 ═ CR12-, -C6H4-, -C (R13) (R14) -, -Si (R15) (R16) -, or-N (R17) -; r11 to R17 are represented, identically or differently, by one of a hydrogen atom, a methyl group, a silylmethyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a phenyl group, a tolyl group, a xylyl group, a trimethylphenyl group, an isopropylphenyl group, a tert-butylphenyl group, a biphenyl group, a naphthyl group, a pyridyl group, a pyridazinyl group, a pyrazinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, a cyanophenyl group or a carbazolyl group;
further, each of R3 to R9 and R11 to R17 independently represents a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted pyridyl group;
r10 represents a hydrogen atom, a fluorine atom, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted pyridyl group;
the substituent is selected from one or more of fluorine atoms, cyano groups, methyl groups, ethyl groups, propyl groups, isopropyl groups, tert-butyl groups, pentyl groups, phenyl groups, naphthyl groups, biphenyl groups, pyridyl groups, furyl groups, carbazolyl groups or thienyl groups.
Further, the structure of the general formula (1) is:
l represents a single bond (L-1), and the structure of the general formula (2) has the meanings listed in the following table;
Figure BDA0001803318480000151
Figure BDA0001803318480000161
Figure BDA0001803318480000171
Figure BDA0001803318480000181
further, the organic compound with benzo [1,2-b:5, 4-b' ] dibenzofuran as the core can also be selected from one of the following compounds:
compounds I-1 to I-693;
compounds I-694 to I-1386, which in turn have the same structure as compounds I-1 to I-693, except that L is L-2;
compounds I-1387 to I-2079, which in turn have the same structure as compounds I-1 to I-693 except that L is L-3;
compounds I-2080 to I-2772, which in turn have the same structure as compounds I-1 to I-693, except that L is L-4;
compounds I-2773-I-3465, which in turn have the same structure as compounds I-1-I-693 except that L is L-5;
compounds I-3466 to I-4158, which in turn have the same structure as compounds I-1 to I-693, except that L is L-6;
compounds I-4159 to I-4851, which in turn have the same structure as compounds I-1 to I-693, except that L is L-7;
compounds I-4852-I-5544 having in sequence the same structures as compounds I-1-I-693 except that L is L-8;
compounds I-5545-I-6237 having the same structure as compounds I-1-I-693 in that order, except that L is L-9;
compounds I-6238-I-6930 having the same structure as compounds I-1-I-693 in that order, except that L is L-10;
compounds I-6931-I-7623, I-7624-I-8316, I-8317-I-9009, I-9010-I-9702, I-9703-I-10395, I-10396-I-11088, I-11089-I-11781, I-11782-I-12474, I-12475-I-13167 and I-13168-I-13860, which respectively have the same structures as the compounds I-1-I-693 in sequence, and have the difference that L is L-11, L-12, L-13, L-14, L-15, L-16, L-17, L-18, L-19 and L-20;
still further, specific compounds of the general formula (1) are:
Figure BDA0001803318480000191
Figure BDA0001803318480000201
Figure BDA0001803318480000211
Figure BDA0001803318480000221
Figure BDA0001803318480000231
Figure BDA0001803318480000241
Figure BDA0001803318480000251
Figure BDA0001803318480000261
Figure BDA0001803318480000271
Figure BDA0001803318480000272
any one of them.
It is to be understood that the specific compounds listed above are merely illustrative of the invention and are not intended to limit the invention.
Furthermore, the invention also provides a preparation method of the organic compound taking benzo [1,2-b:5, 4-b' ] dibenzofuran as the core. The compound disclosed by the invention is simple in preparation method, wide in market prospect and suitable for large-scale popularization and application.
The reaction equation for preparing the organic compound is:
Figure BDA0001803318480000273
the preparation method comprises the following steps:
under the protection of nitrogen, sequentially weighing an intermediate D, a raw material F, sodium tert-butoxide, Pd2(dba)3 and tri-tert-butylphosphine, adding toluene, stirring and mixing, heating to 100-120 ℃, carrying out reflux reaction for 12-24 hours, sampling a sample, and displaying that no intermediate D remains and the reaction is complete; naturally cooling to room temperature, filtering, decompressing and rotary steaming the filtrate until no fraction is produced, and passing through a neutral silica gel column to obtain a target product; the molar ratio of the intermediate D to the raw material F is 1: 1-2; the molar ratio of the Pd2(dba)3 to the intermediate D is 0.006-0.02: 1, and the molar ratio of the tri-tert-butylphosphine to the intermediate D is 0.006-0.02: 1; the molar ratio of the sodium tert-butoxide to the intermediate D is 2.0-3.0: 1; the toluene amount is 0.01mol of intermediate, 150ml of toluene is added.
Furthermore, the invention also provides an organic electroluminescent device. When the compound is applied to an OLED device, the structure of the device is optimized, so that high film stability can be kept, the photoelectric property of the OLED device can be effectively improved, and the service life of the OLED device can be effectively prolonged.
The technical scheme for solving the technical problems is as follows: an organic electroluminescent element, at least one functional layer contains the compound with benzo [1,2-b:5, 4-b' ] dibenzofuran as core.
On the basis of the technical scheme, the invention can be further improved as follows.
Further, the functional layer is an electron blocking layer and/or a hole transport layer.
Further, the functional layer is a luminescent layer material.
A lighting or display element comprising an organic electroluminescent device as described above.
The invention has the beneficial effects that:
1. the compound of the invention is a compound in which a benzo [1,2-b:5,4-b '] dibenzofuran mother nucleus is connected with a rigid large pi conjugated ring-merging branch chain, contains a benzo [1,2-b:5, 4-b' ] dibenzofuran structure, has very strong rigidity, and has the characteristics of difficult crystallization and aggregation among molecules and good film forming property after connecting a five-membered ring-merging ring or a six-membered ring-merging ring or a seven-membered ring-merging ring; the compound parent nucleus has bipolarity, the branched chain is an electron-donating group, and because the electron-donating capability of the group is different, the HOMO energy levels of the material are different, and the material can be used as materials of different functional layers; in addition, the compound has high triplet state energy level, can effectively block energy loss and is beneficial to energy transfer. Therefore, after the compound is used as an organic electroluminescent functional layer material to be applied to an OLED device, the current efficiency, the power efficiency and the external quantum efficiency of the device are greatly improved; meanwhile, the service life of the device is obviously prolonged.
2. When the compound is applied to an OLED device, the structure of the device is optimized, so that high film stability can be kept, the photoelectric property of the OLED device can be effectively improved, and the service life of the OLED device can be effectively prolonged.
3. The organic electroluminescent device can be applied to illumination or display elements, so that the current efficiency, the power efficiency and the external quantum efficiency of the device are greatly improved; meanwhile, the service life of the device is obviously prolonged, and the OLED luminescent device has a good application effect and a good industrialization prospect.
Drawings
FIG. 1 is a schematic diagram of a device structure to which the compound of the present invention is applied, wherein the components represented by the respective reference numerals are as follows:
1. transparent substrate layer, 2, ITO anode layer, 3, hole injection layer, 4, hole transport layer, 5, electron blocking layer, 6, luminescent layer, 7, hole blocking/electron transport layer, 8, electron injection layer, 9, cathode layer, 10, CPL layer.
FIG. 2 is a graph of the current efficiency of an OLED device of the present invention as a function of temperature.
Fig. 3 is a graph of reverse voltage leakage current test curves of devices fabricated in example 1 and comparative example 3 of the device of the present invention.
Detailed Description
The principles and features of this invention are described below in conjunction with the following drawings, which are set forth by way of illustration only and are not intended to limit the scope of the invention. The structural formulae of the prior art materials referred to herein are as follows:
Figure BDA0001803318480000291
the detection method used herein is as follows：
The triplet energy level T1 was measured by Hitachi F4600 fluorescence spectrometer under the conditions of 2X 10-5A toluene solution of mol/L;
glass transition temperature Tg: measured by differential scanning calorimetry (DSC, DSC204F1 DSC, German Nasicon company), the rate of temperature rise was 10 ℃/min.
Thermal weight loss temperature Td: the weight loss was 0.5% in a nitrogen atmosphere, and the nitrogen flow rate was 20mL/min as measured on a TGA-50H thermogravimetric analyzer of Shimadzu corporation, Japan.
Highest occupied molecular orbital HOMO energy level: is tested by an ionization energy testing system (IPS3) in an atmospheric environment.
Cyclic voltammetric stability: the redox characteristics of the material are observed through cyclic voltammetry to identify, and the test conditions are as follows: dissolving a test sample in a mixed solvent of dichloromethane and acetonitrile at a volume ratio of 2:1, wherein the concentration is 1mg/mL, the electrolyte is 0.1M organic solution of tetrabutylammonium tetrafluoroborate, and the reference electrode is Ag/Ag+The electrode, the counter electrode is a titanium plate, the working electrode is an ITO electrode, and the cycle time is 20 times.
Hole mobility: the material was fabricated into single charge devices and tested by the SCLC method.
Synthesis of intermediate D
Figure BDA0001803318480000292
Figure BDA0001803318480000301
(1) Weighing a raw material E and a raw material G, and dissolving the raw materials in a toluene-ethanol mixed solvent with a volume ratio of 1.5-3.0: 1; then adding Na2CO3 aqueous solution and Pd (PPh3) 4; stirring the mixed solution at 90-110 ℃ for reaction for 10-24 hours under an inert atmosphere, cooling to room temperature, filtering the reaction solution, performing rotary evaporation on the filtrate, and passing through a silica gel column to obtain an intermediate H; the molar ratio of the raw material E to the raw material G is 1: 1.5-3.0; the molar ratio of the Pd (PPh3)4 to the raw material E is 0.006-0.02: 1; the molar ratio of the Na2CO3 to the raw material E is 2.0-3.0: 1; 30-40ml of toluene and 15-20ml of ethanol are added into the raw material E with the dosage of the toluene and ethanol mixed solvent being 0.01 mol;
(2) weighing the intermediate H and p-toluenesulfonic acid under the protection of nitrogen, dissolving with toluene, heating to 90-110 ℃, and reacting for 10-24 hours; sampling a spot plate, and showing that no intermediate H remains and the reaction is complete; after the reaction is finished, adding a saturated sodium carbonate solution into the reaction system for quenching, extracting with ethyl acetate, separating liquid, drying an organic phase with anhydrous sodium sulfate, decompressing, carrying out rotary evaporation until no fraction is produced, and passing the obtained crude product through a neutral silica gel column to obtain an intermediate D; the molar ratio of the intermediate H to the p-toluenesulfonic acid is 1: 1-1.5; 30-40ml of toluene is added into the intermediate H with the dosage of the toluene being 0.01 mol; adding 5-15ml of saturated sodium carbonate solution into the intermediate H with the dosage of the saturated sodium carbonate solution being 0.01 mol; adding 30-45ml of ethyl acetate into the intermediate H with the dosage of the ethyl acetate being 0.01mol, and adding the ethyl acetate into the intermediate H in three times;
this is exemplified by the synthesis of intermediate D1:
Figure BDA0001803318480000302
(1) a500 mL three-necked flask was charged with 0.05mol of E and 0.1mol of G-1 under nitrogen atmosphere, dissolved in a mixed solvent (180mL of toluene and 90mL of ethanol), and then charged with 0.15mol of aqueous Na2CO3 solution (2M), stirred with nitrogen for 1 hour, and then charged with 0.0005mol of Pd (PPh3)4, heated to 105 ℃ for 15 hours, sampled and spotted on a plate, and the reaction was completed. Naturally cooling, filtering, rotatably evaporating filtrate, and passing through a silica gel column to obtain an intermediate H-1 with the HPLC purity of 99.3 percent and the yield of 61.5 percent.
Elemental analysis structure (molecular formula C18H11BrO 3): theoretical value C, 60.87; h, 3.12; br, 22.50; o, 13.51; test values are: c, 60.85; h, 3.14; br, 22.51; and O, 13.50. ESI-MS (M/z) (M +): theoretical value is 353.99, found 354.21.
(3) Adding 0.03mol of intermediate H-1 and 0.036mol of p-toluenesulfonic acid into a 250mL three-neck flask under the protection of nitrogen, dissolving the mixture by using 100mL of toluene, heating to 100 ℃, and reacting for 15 hours; sampling a spot plate, and showing that no intermediate H-1 remains and the reaction is complete; after the reaction, 30ml of saturated sodium carbonate solution was added to the reaction system to quench, and the mixture was extracted with (30ml x 3) ethyl acetate, separated, the organic phase was dried over anhydrous sodium sulfate and then rotary evaporated under reduced pressure until no fraction was obtained, and the obtained crude product was passed through a neutral silica gel column to obtain intermediate D-1 with HPLC purity of 99.2% and yield of 55.4%.
Elemental analysis structure (molecular formula C18H9BrO 2): theoretical value C, 64.12; h, 2.69; br, 23.70; o, 9.49; test values are: c, 64.10; h, 2.67; br, 23.73; and O, 9.50. ESI-MS (M/z) (M +): theoretical value is 335.98, found 336.26.
Synthesizing an intermediate D according to a preparation method of the intermediate D-1, wherein the synthesis of the intermediate D comprises two steps: the raw material E and the raw material G react through Suzuki to generate an intermediate H; the intermediate H undergoes a cyclization reaction to generate an intermediate D, and the specific structure is shown in Table 1.
TABLE 1
Figure BDA0001803318480000311
Example 1: preparation of Compound 1
Figure BDA0001803318480000312
0.01mol of intermediate D-1 and 0.015mol of starting material were charged into a 500ml three-necked flask under a nitrogen atmosphereF-1, 0.03mol of sodium tert-butoxide, 5X 10-5mol Pd2(dba)3And 5X 10-5After the reaction was completed, 150ml of toluene was added to dissolve tri-t-butylphosphine, and the mixture was heated to 100 ℃ and refluxed for 24 hours, and the reaction was observed by TLC. Naturally cooling to room temperature, filtering, and rotatably evaporating the filtrate until no fraction is obtained. The resulting material was purified by silica gel column (petroleum ether as eluent) to give the desired product in 99.6% purity and 76.5% yield.
Elemental analysis Structure (molecular formula C)36H19NO3): theoretical value: c, 84.20; h, 3.73; n, 2.73; o, 9.35; test values are: c, 84.22; h, 3.71; n, 2.72; and O, 9.35. ESI-MS (M/z) (M)+): theoretical value is 513.14, found 513.46.
Example 2: preparation of Compound 17
Figure BDA0001803318480000321
The compound is prepared according to the synthetic method of the compound 1, except that the intermediate D-2 is used for replacing the intermediate D-1, the raw material F-2 is used for replacing the raw material F-1, the purity of the obtained target product is 99.7 percent, and the yield is 72.6 percent.
Elemental analysis structure (molecular formula C41H22N2O 3): theoretical value: c, 83.38; h, 3.75; n, 4.74; o, 8.13; test values are: c, 83.37; h, 3.74; n, 4.73; and O, 8.16. ESI-MS (M/z) (M +): theoretical value is 590.16, found 590.44.
Example 3: preparation of Compound 28
Figure BDA0001803318480000322
The compound was prepared according to the synthetic method of the compound 1 except that the intermediate D-3 was used instead of the intermediate D-1 and the raw material F-3 was used instead of the raw material F-1, and the purity of the obtained objective product was 99.5% and the yield was 75.9%.
Elemental analysis structure (molecular formula C42H23NO 3): theoretical value: c, 85.55; h, 3.93; n, 2.38; o, 8.14; test values are: c, 85.54; h, 3.94; n, 2.37; and O, 8.15. ESI-MS (M/z) (M +): theoretical value is 589.17, found 589.50.
Example 4: preparation of Compound 35
Figure BDA0001803318480000323
Prepared according to the synthetic method of the compound 1, except that the intermediate D-4 is used for replacing the intermediate D-1, the raw material F-4 is used for replacing the raw material F-1, the purity of the obtained target product is 99.6 percent, and the yield is 78.2 percent.
Elemental analysis structure (molecular formula C42H23NO 3): theoretical value: c, 85.55; h, 3.93; n, 2.38; o, 8.14; test values are: c, 85.56; h, 3.92; n, 2.36; and O, 8.16. ESI-MS (M/z) (M +): theoretical value is 589.17, found 589.53.
Example 5: preparation of Compound 45
Figure BDA0001803318480000324
Prepared according to the synthesis method of the compound 1, except that the intermediate D-5 is used for replacing the intermediate D-1, the raw material F-5 is used for replacing the raw material F-1, the purity of the obtained target product is 99.9 percent, and the yield is 74.4 percent.
Elemental analysis structure (molecular formula C39H25NO 2): theoretical value: c, 86.80; h, 4.67; n, 2.60; o, 5.93; test values are: c, 86.81; h, 4.65; n, 2.61; and O, 5.93. ESI-MS (M/z) (M +): theoretical value is 539.19, found 539.57.
Example 6: preparation of Compound 56
Figure BDA0001803318480000331
The compound is prepared according to the synthetic method of the compound 1, except that the intermediate D-3 is used for replacing the intermediate D-1, the raw material F-6 is used for replacing the raw material F-1, the purity of the obtained target product is 99.7 percent, and the yield is 76.1 percent.
Elemental analysis structure (molecular formula C45H29NO 2): theoretical value: c, 87.78; h, 4.75; n, 2.27; o, 5.20; test values are: c, 87.76; h, 4.77; n, 2.25; and O, 5.22. ESI-MS (M/z) (M +): theoretical value is 615.22, found 615.44.
Example 7: preparation of Compound 72
Figure BDA0001803318480000332
The compound is prepared according to the synthetic method of the compound 1, except that the intermediate D-5 is used for replacing the intermediate D-1, the raw material F-7 is used for replacing the raw material F-1, the purity of the obtained target product is 99.8 percent, and the yield is 74.2 percent.
Elemental analysis structure (molecular formula C42H24N2O 2): theoretical value: c, 85.70; h, 4.11; n, 4.76; o, 5.44; test values are: c, 85.71; h, 4.12; n, 4.75; and O, 5.42. ESI-MS (M/z) (M +): theoretical value is 588.18, found 588.56.
Example 8: preparation of Compound 84
Figure BDA0001803318480000333
The compound is prepared according to the synthetic method of the compound 1, except that the intermediate D-6 is used for replacing the intermediate D-1, the raw material F-8 is used for replacing the raw material F-1, the purity of the obtained target product is 99.6 percent, and the yield is 75.3 percent.
Elemental analysis structure (molecular formula C48H28N2O 2): theoretical value: c, 86.73; h, 4.25; n, 4.21; o, 4.81; test values are: c, 86.71; h, 4.24; n, 4.23; and O, 4.82. ESI-MS (M/z) (M +): theoretical value is 664.22, found 664.58.
Example 9: preparation of Compound 96
Figure BDA0001803318480000334
The compound is prepared according to the synthetic method of the compound 1, except that the intermediate D-5 is used for replacing the intermediate D-1, the raw material F-9 is used for replacing the raw material F-1, the purity of the obtained target product is 99.9 percent, and the yield is 78.2 percent.
Elemental analysis structure (molecular formula C48H28N2O 2): theoretical value: c, 86.73; h, 4.25; n, 4.21; o, 4.81; test values are: c, 86.72; h, 4.24; n, 4.22; and O, 4.82. ESI-MS (M/z) (M +): theoretical value is 664.22, found 664.53. .
Example 10: preparation of Compound 111
Figure BDA0001803318480000341
Prepared according to the synthesis method of the compound 1, except that the intermediate D-6 is used for replacing the intermediate D-1, the raw material F-10 is used for replacing the raw material F-1, the purity of the obtained target product is 99.5 percent, and the yield is 73.9 percent.
Elemental analysis structure (molecular formula C46H25NO 3): theoretical value: c, 86.37; h, 3.94; n, 2.19; o, 7.50; test values are: c, 86.35; h, 3.92; n, 2.20; o, 7.53. ESI-MS (M/z) (M +): theoretical value is 639.18, found 639.51.
Example 11: preparation of Compound 132
Figure BDA0001803318480000342
Prepared according to the synthesis method of the compound 1, except that the intermediate D-5 is used for replacing the intermediate D-1, the raw material F-11 is used for replacing the raw material F-1, the purity of the obtained target product is 99.7 percent, and the yield is 77.9 percent.
Elemental analysis structure (molecular formula C42H21NO 4): theoretical value: c, 83.57; h, 3.51; n, 2.32; o, 10.60; test values are: c, 83.54; h, 3.53; n, 2.31; o, 10.62. ESI-MS (M/z) (M +): theoretical value is 603.15, found 603.47.
Example 12: preparation of Compound 143
Figure BDA0001803318480000343
The compound was prepared according to the synthetic method of the compound 1 except that the intermediate D-5 was used instead of the intermediate D-1 and the starting material F-12 was used instead of the starting material F-1, and the purity of the obtained objective product was 99.8% and the yield was 75.9%.
Elemental analysis structure (molecular formula C36H19NO 4): theoretical value: c, 81.65; h, 3.62; n, 2.65; o, 12.08; test values are: c, 81.64; h, 3.63; n, 2.66; and O, 12.07. ESI-MS (M/z) (M +): theoretical value is 529.13, found 529.37.
Example 13: preparation of Compound 163
Figure BDA0001803318480000344
Prepared according to the synthesis method of the compound 1, except that the intermediate D-7 is used for replacing the intermediate D-1, the raw material F-13 is used for replacing the raw material F-1, the purity of the obtained target product is 99.8 percent, and the yield is 77.4 percent.
Elemental analysis structure (molecular formula C49H37NO 3): theoretical value: c, 85.56; h, 5.42; n, 2.04; o, 6.98; test values are: c, 85.55; h, 5.43; n, 2.05; and O, 6.97. ESI-MS (M/z) (M +): theoretical value is 687.28, found 687.62.
Example 14: preparation of Compound 190
Figure BDA0001803318480000345
Prepared according to the synthesis method of the compound 1, except that the intermediate D-5 is used for replacing the intermediate D-1, the raw material F-14 is used for replacing the raw material F-1, the purity of the obtained target product is 99.9 percent, and the yield is 75.7 percent.
Elemental analysis structure (molecular formula C40H27NO 2): theoretical value: c, 86.78; h, 4.92; n, 2.53; o, 5.78; test values are: c, 86.76; h, 4.94; n, 2.51; o, 5.79. ESI-MS (M/z) (M +): theoretical value is 553.20, found 553.44.
Example 15: preparation of Compound 206
Figure BDA0001803318480000351
Prepared according to the synthesis method of the compound 1, except that the intermediate D-8 is used for replacing the intermediate D-1, the raw material F-15 is used for replacing the raw material F-1, the purity of the obtained target product is 99.6 percent, and the yield is 77.7 percent.
Elemental analysis structure (molecular formula C39H25NO 3): theoretical value: c, 84.31; h, 4.54; n, 2.52; o, 8.64; test values are: c, 84.33; h, 4.51; n, 2.53; and O, 8.63. ESI-MS (M/z) (M +): theoretical value is 555.18, found 555.45.
Example 16: preparation of Compound 220
Figure BDA0001803318480000352
The compound is prepared according to the synthetic method of the compound 1, except that the intermediate D-9 is used for replacing the intermediate D-1, the raw material F-16 is used for replacing the raw material F-1, the purity of the obtained target product is 99.8 percent, and the yield is 78.0 percent.
Elemental analysis structure (molecular formula C45H29NO 3): theoretical value: c, 85.56; h, 4.63; n, 2.22; o, 7.60; test value C, 85.54; h, 4.64; n, 2.21; and O, 7.61. ESI-MS (M/z) (M +): theoretical value is 631.21, found 631.55.
Example 17: preparation of Compound 232
Figure BDA0001803318480000353
Prepared according to the synthesis method of the compound 1, except that the intermediate D-6 is used for replacing the intermediate D-1, the raw material F-16 is used for replacing the raw material F-1, the purity of the obtained target product is 99.7 percent, and the yield is 73.3 percent.
Elemental analysis structure (molecular formula C45H29NO 3): theoretical value: c, 85.56; h, 4.63; n, 2.22; o, 7.60; test values are: c, 85.55; h, 4.62; n, 2.21; and O, 7.62. ESI-MS (M/z) (M +): theoretical value is 631.21, found 631.58.
Example 18: preparation of Compound 258
Figure BDA0001803318480000354
The compound is prepared according to the synthetic method of the compound 1, except that the intermediate D-6 is used for replacing the intermediate D-1, the raw material F-17 is used for replacing the raw material F-1, the purity of the obtained target product is 99.8 percent, and the yield is 76.1 percent.
Elemental analysis structure (molecular formula C48H35NO 2): theoretical value: c, 87.64; h, 5.36; n, 2.13; o, 4.86; test values are: c, 87.63; h, 5.35; n, 2.14; and O, 4.88. ESI-MS (M/z) (M +): theoretical value is 657.27, found 657.64.
Example 19: preparation of Compound 269
Figure BDA0001803318480000361
The compound is prepared according to the synthetic method of the compound 1, except that the intermediate D-5 is used for replacing the intermediate D-1, the raw material F-18 is used for replacing the raw material F-1, the purity of the obtained target product is 99.9 percent, and the yield is 78.4 percent.
Elemental analysis structure (molecular formula C45H30N2O 2): theoretical value: c, 85.69; h, 4.79; n, 4.44; o, 5.07; test values are: c, 85.67; h, 4.78; n, 4.46; and O, 5.09. ESI-MS (M/z) (M +): theoretical value is 630.23, found 630.52.
Example 20: preparation of Compound 293
Figure BDA0001803318480000362
The compound was prepared according to the synthetic method of the compound 1 except that the intermediate D-5 was used instead of the intermediate D-1 and the starting material F-19 was used instead of the starting material F-1, and the purity of the obtained objective product was 99.6% and the yield was 74.7%.
Elemental analysis structure (molecular formula C43H27NO 3): theoretical value: c, 85.27; h, 4.49; n, 2.31; o, 7.92; test values are: c, 85.26; h, 4.48; n, 2.33; and O, 7.93. ESI-MS (M/z) (M +): theoretical value is 605.20, found 605.54.
Example 21: preparation of Compound 310
Figure BDA0001803318480000363
The compound was prepared according to the synthetic method of the compound 1 except that the intermediate D-1 was replaced with the intermediate D-5 and the starting material F-1 was replaced with the starting material F-20, and the purity of the obtained objective product was 99.5% and the yield was 75.5%.
Elemental analysis structure (molecular formula C49H29NO 3): theoretical value: c, 86.58; h, 4.30; n, 2.06; o, 7.06; test values are: c, 86.56; h, 4.32; n, 2.07; and O, 7.05. ESI-MS (M/z) (M +): theoretical value is 679.21, found 679.46.
Example 22: preparation of Compound 317
Figure BDA0001803318480000364
Prepared according to the synthesis method of the compound 1, except that the intermediate D-5 is used for replacing the intermediate D-1, the raw material F-21 is used for replacing the raw material F-1, the purity of the obtained target product is 99.7 percent, and the yield is 77.2 percent.
Elemental analysis structure (molecular formula C52H35NO 2): theoretical value: c, 88.48; h, 5.00; n, 1.98; o, 4.53; test values are: c, 88.45; h, 5.02; n, 1.99; and O, 4.54. ESI-MS (M/z) (M +): theoretical value is 705.27, found 705.55.
Example 23: preparation of Compound 333
Figure BDA0001803318480000371
The compound is prepared according to the synthetic method of the compound 1, except that the intermediate D-5 is used for replacing the intermediate D-1, the raw material F-22 is used for replacing the raw material F-1, the purity of the obtained target product is 99.8 percent, and the yield is 78.5 percent.
Elemental analysis structure (molecular formula C49H27NO 3): theoretical value: c, 86.84; h, 4.02; n, 2.07; o, 7.08; test values are: c, 86.83; h, 4.02; n, 2.09; and O, 7.06. ESI-MS (M/z) (M +): theoretical value is 677.20, found 677.54.
Example 24: preparation of Compound 354
Figure BDA0001803318480000372
Prepared according to the synthesis method of the compound 1, except that the intermediate D-5 is used for replacing the intermediate D-1, the raw material F-23 is used for replacing the raw material F-1, the purity of the obtained target product is 99.6 percent, and the yield is 77.5 percent.
Elemental analysis structure (molecular formula C52H33NO 3): theoretical value: c, 86.77; h, 4.62; n, 1.95; o, 6.67; test values are: c, 86.75; h, 4.64; n, 1.96; o, 6.65. ESI-MS (M/z) (M +): theoretical value is 719.25, found 719.55.
Example 25: preparation of Compound 389
Figure BDA0001803318480000373
Prepared according to the synthesis method of the compound 1, except that the intermediate D-10 is used for replacing the intermediate D-1, the raw material F-24 is used for replacing the raw material F-1, the purity of the obtained target product is 99.8 percent, and the yield is 79.8 percent.
Elemental analysis structure (molecular formula C44H25N3O 2): theoretical value: c, 84.19; h, 4.01; n, 6.69; o, 5.105; test values are: c, 84.17; h, 4.02; n, 6.70; and O, 5.11. ESI-MS (M/z) (M +): theoretical value is 627.19, found 627.54.
Example 26: preparation of Compound 398
Figure BDA0001803318480000374
The compound was prepared according to the synthetic method of the compound 1 except that the intermediate D-5 was used instead of the intermediate D-1 and the raw material F-25 was used instead of the raw material F-1, and the purity of the obtained objective product was 99.7% and the yield was 76.4%.
Elemental analysis structure (molecular formula C36H19NO 3S): theoretical value: c, 79.25; h, 3.51; n, 2.57; o, 8.80; s, 5.88; test values are: c, 79.26; h, 3.52; n, 2.56; o, 8.81; and S, 5.85. ESI-MS (M/z) (M +): theoretical value is 545.11, found 545.35.
The organic compound is used in a light-emitting device, has high glass transition temperature (Tg) and triplet state energy level (T1), and suitable HOMO and LUMO energy levels, can be used as a hole transport/electron blocking material, and can also be used as a light-emitting layer material. The compound prepared in the example of the present invention and the existing material were respectively tested for thermal performance, T1 energy level and HOMO energy level, and the results are shown in table 2.
TABLE 2
Figure BDA0001803318480000381
Figure BDA0001803318480000391
The data in the table show that the organic compound prepared by the invention has high glass transition temperature, can improve the phase stability of the material film, and further improves the service life of the device; the material disclosed by the invention is suitable for the HOMO energy level, and also has a high triplet state energy level (T1), so that the energy loss of a light-emitting layer can be blocked, and the light-emitting efficiency of a device is improved. Therefore, the organic material containing benzo [1,2-b:5, 4-b' ] dibenzofuran can effectively improve the luminous efficiency and the service life of the device after being applied to different functional layers of an OLED device.
Preparation of the organic electroluminescent device of the present invention
The effect of the synthesized compound of the present invention as a hole transport layer material or an electron blocking layer material in a device is explained in detail below by device examples 1 to 30 and device comparative example 1. Device examples 2-30 and device comparative example 1 compared with device example 1, the manufacturing process of the device is completely the same, the same substrate material and electrode material are adopted, and the film thickness of the electrode material is kept consistent. Except that the hole transport layer material or the electron barrier layer material and the luminescent layer doping material are changed. The structural composition of the resulting device of each example is shown in table 3. The test results of the resulting devices are shown in table 4.
Device example 1
Transparent substrate layer/ITO anode layer/hole injection layer (HAT-CN, thickness 10 nm)/hole transport layer (HTR, thickness 60 nm)/electron blocking layer (EBR, thickness 20 nm)/light emitting layer (compounds 1 and GHA and GDA mixed in a weight ratio of 45:45:10, thickness 40 nm)/hole blocking/electron transport layer (ETR and Liq mixed in a weight ratio of 1:1, thickness 35 nm)/electron injection layer (LiF, thickness 1 nm)/cathode layer (Mg and Ag mixed in a weight ratio of 9:1, thickness 15nm)/CPL layer (compound CPR, thickness 70 nm).
The preparation process comprises the following steps:
as shown in fig. 1, the transparent substrate layer 1 is a transparent substrate, such as a transparent PI film, glass, or the like. The ITO anode layer 2 (having a film thickness of 150nm) was washed by alkali washing, pure water washing, drying, and then ultraviolet-ozone washing to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, HAT-CN having a film thickness of 10nm was deposited by a vacuum deposition apparatus to be used as the hole injection layer 3. Next, an HTR layer was deposited by vapor deposition to a thickness of 60nm as a hole transport layer. EBR was then evaporated to a thickness of 20nm as an electron blocking layer. After the evaporation of the electron barrier layer material is finished, a light-emitting layer 6 of the OLED light-emitting device is manufactured, the structure of the light-emitting layer comprises the compound 1 and the compound GHA which are prepared in the embodiment of the invention and are used as main body materials, the GDA is used as a doping material, the mass ratio of the compound 1 to the GHA to the GDA is 45:45:10, and the thickness is 40 nm; . After the light-emitting layer 6, the electron transport layer materials ETR and Liq, which were mixed at a weight ratio of 50:50:10 and had a film thickness of 35nm, were vacuum evaporated to form a hole blocking/electron transport layer 7. On the hole-blocking/electron-transporting layer 7, a lithium fluoride (LiF) layer having a film thickness of 1nm was deposited by evaporation, and this layer was an electron-injecting layer 8. On the electron injection layer 8, Mg: an Ag electrode layer, which is used as the cathode layer 9. CPR of 70nm was vacuum-deposited on the cathode layer 9 as the CPL layer 10. After the OLED light emitting device was completed as above, the anode and cathode were connected by a known driving circuit, and the current efficiency of the device and the lifetime of the device were measured.
TABLE 3
Figure BDA0001803318480000401
Figure BDA0001803318480000411
Figure BDA0001803318480000421
Note: comparative example of representative device
TABLE 4
Figure BDA0001803318480000422
Figure BDA0001803318480000431
Note: representative comparative examples
LT95 refers to a current density of 20mA/cm2In this case, the time taken for the luminance of the device to decay to 95%;
the life test system is a life tester of a Korean pulse science M6000 type OLED device.
From the results in table 4, it can be seen that the organic compound prepared by the present invention can be applied to the fabrication of OLED light emitting devices, and compared with comparative device 1, the efficiency and lifetime of the organic compound are greatly improved compared with those of known OLED materials, and especially the service life of the organic compound is greatly prolonged. Further, the efficiency of the OLED device prepared by the material is stable when the OLED device works at low temperature and high temperature, and the results of efficiency tests of device examples 3, 12 and 21 and device comparative example 1 at the temperature range of-10 to 80 ℃ are shown in Table 5 and FIG. 2.
TABLE 5
Figure BDA0001803318480000432
As can be seen from the data in table 5 and fig. 2, device examples 3, 12 and 21 are device structures in which the material of the present invention and the known material are combined, and compared with device comparative example 1, the efficiency is high at low temperature, and the efficiency is smoothly increased during the temperature increase process.
To further test the beneficial effects of the compounds of the present invention, the devices prepared in example 3 and comparative example 1 were tested for reverse voltage leakage current, and the test data is shown in fig. 3. As can be seen from fig. 3, the device example 3 using the compound of the present invention has a smaller leakage current and a more stable current curve than the device made in the device comparative example 1, and thus the material of the present invention has a longer lifetime after being applied to the device.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.

Claims (10)

1. A compound with benzo [1,2-b:5, 4-b' ] dibenzofuran as core, which is characterized in that the structure of the compound is shown as general formula (1):
Figure RE-FDA0001856293340000011
in the general formula (1), L represents a single bond, a substituted or unsubstituted C6-30 arylene group, a substituted or unsubstituted 5-to 30-membered heteroarylene group containing one or more hetero atoms;
in the general formula (1), R represents a structure shown in a general formula (2);
Figure RE-FDA0001856293340000012
in the general formula (2), R1 and R2 are each independently a hydrogen atom, a structure represented by the general formula (3) or the general formula (4); r1 is the same or different from R2; r1 and R2 are not hydrogen atoms at the same time;
Figure RE-FDA0001856293340000013
in the general formulae (2) and (4), X1, X2, and X3 each independently represents a single bond, an oxygen atom, a sulfur atom, -CR3 ═ CR4 —, and,
Figure RE-FDA0001856293340000014
-one of C (R5) (R6) -, -Si (R7) (R8) -or-N (R9) -; and X2 and X3 are not single bonds at the same time;
R3to R9Each independently represents a hydrogen atom, a C1-20 linear alkyl group, a C3-20 branched alkyl group, a C1-20 linear alkyl substituted silyl group, a C3-20 branched alkyl substituted silyl group, a substituted or unsubstituted C6-30 aryl group, a substituted or unsubstituted 5-30 containing one or more heteroatomsOne of a membered heteroaryl; r3And R4、R5And R6May also be bonded to each other to form a 5-to 30-membered aliphatic, aromatic or heteroaromatic ring;
the substituent for substituting the above-mentioned substitutable group is selected from one or more of halogen, cyano, C6-30 aryl, and 5-to 30-membered heteroaryl containing one or more hetero atoms;
the heteroatom is selected from an oxygen atom, a sulfur atom or a nitrogen atom.
2. A compound of claim 1, benzo [1,2-b:5, 4-b']A compound having a dibenzofuran core represented by the general formula (1), wherein L represents a single bond (L-1),
Figure RE-FDA0001856293340000021
Figure RE-FDA0001856293340000022
Wherein Z in L-2 to L-20, identically or differently at each occurrence, is denoted C-R10Or N; the R is10Each occurrence, identically or differently, being represented by a hydrogen atom, halogen, cyano, C1-20Alkyl of (C)1-20Alkenyl of (a), substituted or unsubstituted C6-30One of an aryl group and a substituted or unsubstituted 5-to 30-membered heteroaryl group containing one or more heteroatoms; two or more adjacent R10May be bonded to each other to form a ring;
and
Figure RE-FDA0001856293340000023
and Z at the R bond is C.
3. The compound of claim 1, wherein the compound represented by the general formula (2) is represented by
Figure RE-FDA0001856293340000024
Figure RE-FDA0001856293340000031
Figure RE-FDA0001856293340000041
Figure RE-FDA0001856293340000051
Figure RE-FDA0001856293340000061
Figure RE-FDA0001856293340000071
Figure RE-FDA0001856293340000081
Figure RE-FDA0001856293340000091
Figure RE-FDA0001856293340000101
Figure RE-FDA0001856293340000111
Figure RE-FDA0001856293340000121
Figure RE-FDA0001856293340000131
Figure RE-FDA0001856293340000132
Any one of the above;
wherein Y, which may be the same or different, represents an oxygen atom, a sulfur atom, -CR11＝CR12-、
Figure RE-FDA0001856293340000133
-C(R13)(R14)-、-Si(R15)(R16) -or-N (R)17)-；
R11-R17 are respectively and independently one of hydrogen atom, C1-10 linear alkyl, C3-10 branched alkyl, C1-10 linear alkyl substituted silyl, C3-10 branched alkyl substituted silyl, substituted or unsubstituted C6-30 aryl and substituted or unsubstituted 5-30-membered heteroaromatic group containing one or more heteroatoms.
4. A compound of any one of claims 1 to 3, substituted with benzo [1,2-b:5, 4-b']A dibenzofuran-core compound, wherein R is3～R9、R11～R17Each independently represents a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted pyridyl group;
the R is10Represents a hydrogen atom, a fluorine atom, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted pyridyl group;
the substituent is selected from one or more of fluorine atoms, cyano groups, methyl groups, ethyl groups, propyl groups, isopropyl groups, tert-butyl groups, pentyl groups, phenyl groups, naphthyl groups, biphenyl groups, pyridyl groups, furyl groups, carbazolyl groups or thienyl groups.
5. The benzo [1,2-b:5, 4-b' ] dibenzofuran-cored compound of claim 1, wherein the specific compound of formula (1) is:
Figure RE-FDA0001856293340000141
Figure RE-FDA0001856293340000151
Figure RE-FDA0001856293340000161
Figure RE-FDA0001856293340000171
Figure RE-FDA0001856293340000181
Figure RE-FDA0001856293340000191
Figure RE-FDA0001856293340000201
Figure RE-FDA0001856293340000211
Figure RE-FDA0001856293340000221
Figure RE-FDA0001856293340000222
any one of them.
6. A method for producing an organic compound according to any one of claims 1 to 5, wherein the method involves a reaction equation:
Figure RE-FDA0001856293340000223
the preparation method comprises the following steps:
under the protection of nitrogen, sequentially weighing the intermediate D, the raw material F, sodium tert-butoxide and Pd2(dba)3Adding toluene into tri-tert-butylphosphine, stirring and mixing, heating to 100-120 ℃, carrying out reflux reaction for 12-24 hours, sampling a sample point plate, and indicating that no intermediate D remains and the reaction is complete; naturally cooling to room temperature, filtering, decompressing and rotary steaming the filtrate until no fraction is produced, and passing through a neutral silica gel column to obtain a target product; the molar ratio of the intermediate D to the raw material F is 1: 1-2; the Pd2(dba)3The molar ratio of the tri-tert-butylphosphine to the intermediate D is 0.006-0.02: 1, and the molar ratio of the tri-tert-butylphosphine to the intermediate D is 0.006-0.02: 1; the molar ratio of the sodium tert-butoxide to the intermediate D is 2.0-3.0: 1; the amount of toluene used was 0.01mol of intermediate D to 150ml of toluene.
7. An organic electroluminescent element, characterized in that at least one functional layer contains a compound having benzo [1,2-b:5, 4-b' ] dibenzofuran as claimed in any one of claims 1 to 5 as a core.
8. The organic electroluminescent device according to claim 7, comprising a hole transport layer/electron blocking layer, wherein the hole transport layer or the electron blocking layer is made of a compound with benzo [1,2-b:5, 4-b' ] dibenzofuran as a core.
9. The organic electroluminescent device according to claim 7, comprising a light-emitting layer, wherein the material of the light-emitting layer is a compound with benzo [1,2-b:5, 4-b' ] dibenzofuran as a core.
10. A lighting or display element comprising an organic electroluminescent device as claimed in claims 7 to 9.
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