Organic compound with dibenzopyrone-like ring as core, preparation method and application thereof, and application of organic electroluminescent device

Abstract

The invention provides an organic compound taking a dibenzopyrone-like fused ring as a core, a preparation method and application of the organic compound, and application of an organic electroluminescent device, and relates to the field of semiconductors. The organic compound provided by the invention takes a dibenzopyrone-like fused ring as a parent nucleus and is connected with a planar rigid branch chain, so that the structure of the material is more stable, the material has high Tg temperature, active C-H bonds in molecules are passivated, and the service life of the organic compound is prolonged; chemical bonds of the organic compound have relatively high bond energy, so that the service life is further prolonged; the combination form of the dibenzopyrone-like fused ring and the planar rigid branched chain structure can effectively increase steric hindrance, slow down efficiency roll-off under high current density, and further prolong the service life; the compound contains a planar rigid branch chain and a specific connection site and connection mode between the planar rigid branch chain and a core structure, so that the intermolecular charge jumping transmission rate can be increased, and the current efficiency is improved.

Description

Technical Field

[0001] The present invention relates to the field of semiconductors, and in particular to an organic compound with a dibenzopyrone-like ring as the core, a preparation method and application thereof, and an application of an organic electroluminescent device. Background Art

[0002] Organic Light Emission Diodes (OLED) devices have a sandwich-like structure, which consists of electrode material layers and functional materials sandwiched between different electrode film layers. When voltage is applied to the electrodes at both ends, the electric field will act on the positive and negative charges of the functional materials, causing the positive and negative charges to further recombine to produce OLED electroluminescence.

[0003] Currently, OLED display technology has been applied in smart phones, tablet computers and other fields, and will further expand to large-size application fields such as televisions. However, compared with actual product application requirements, the current efficiency and service life of OLED devices prepared with existing compounds need to be further improved. Summary of the invention

[0004] The present invention provides an organic compound with a dibenzopyrone-like ring as the core, a preparation method and application thereof, and an application of an organic electroluminescent device. The organic compound of the present invention is applied to an organic electroluminescent device to improve the current efficiency and service life of the OLED device.

[0005] The present invention provides an organic compound with a dibenzopyrone-like ring as the core, having a structure shown in general formula (1.1) or general formula (1.2):

[0006]

[0007] The Z each time independently comprises =N-, =C- or =C(R3)-, and each Z may be the same or different;

[0008] With R a The connected Z is =C-;

[0009] R a Including the structure shown in general formula (2);

[0010]

[0011] In the general formula (2), X1 includes -O-, -S- or -C(R1)(R2)-;

[0012] * is the binding site;

[0013] The R comprises a structure represented by general formula (3) or general formula (4);

[0014]

[0015] In the general formula (3), X2 represents -O-, -S-, -N(R4)- or -C(R5)(R6)-;

[0016] Z1 each time independently comprises =N-, =C- or =C(R7)-, and each Z1 may be the same or different;

[0017] Z1 connected to L1 is =C-;

[0018] The L1 and L2 independently include one of a single bond, a substituted arylene group, an unsubstituted arylene group, a substituted heteroarylene group and an unsubstituted heteroarylene group;

[0019] R1, R2, R3, R4, R5, R6, R7 and R b Independently include one of a hydrogen atom, a deuterium atom, a substituted alkyl group, an unsubstituted alkyl group, a substituted aryl group, an unsubstituted aryl group, a substituted heteroaryl group and an unsubstituted heteroaryl group.

[0020] The organic compound of the present invention uses a dibenzopyrone-like ring as a parent core and is connected with a planar rigid side chain. The chemical bonds in the molecule are not easy to rotate, so that the structure of the material is more stable and has a high Tg temperature, and the active CH bonds in the molecule are passivated, thereby improving the stability and service life of the organic compound in a film state; and the chemical bonds of the organic compound of the present invention all have a high bond energy, which can effectively inhibit the decomposition of the molecule under the action of an electric field and light, and further improve the stability and service life of the device; in addition, the combination of the dibenzopyrone-like ring and the planar rigid side chain structure of the present invention can effectively increase the steric hindrance between molecules, slow down the efficiency roll-off under high current density, and further improve the device life; the compound of the present invention contains a planar rigid side chain and a specific connection site and connection method between the side chain and the core structure, which can increase the rate of charge "jumping" transmission between molecules, thereby improving the carrier mobility and current efficiency, which can reduce the device power consumption and improve the device life, especially the high-temperature device life.

[0021] The dibenzopyrone-like annular parent core in the compound of the present invention enables the molecule to have a suitable LUMO energy level and a degree of conjugated delocalization of the extended acceptor fragment, and can effectively reduce the turn-on voltage and driving voltage of the device when used as an electronic host in the light-emitting layer, a hole blocking layer or an electron transport layer material.

[0022] The compound of the present invention has a relatively high excited state reorganization energy, and when used as a main body of a light-emitting layer, can effectively improve the device life; when used in combination with a hole-type main material, the current efficiency and life of the device can be further improved.

[0023] When the compound of the present invention is used as a hole blocking layer, the T1 energy level higher than that of the light-emitting layer can effectively reduce the energy loss of the light-emitting layer, thereby improving the light-emitting efficiency of the material after being applied to the device.

[0024] After the compound of the present invention is used as an organic electroluminescent functional layer material in an OLED device, the current efficiency, power efficiency and external quantum efficiency of the device are greatly improved; at the same time, the device life is significantly improved, and it has a good application effect in OLED light-emitting devices and has a good industrialization prospect. BRIEF DESCRIPTION OF THE DRAWINGS

[0025] Figure 1 This is a structural diagram of the device of comparative application example 1. DETAILED DESCRIPTION

[0026] The present invention provides an organic compound with a dibenzopyrone-like ring as the core, having a structure shown in general formula (1.1) or general formula (1.2):

[0027]

[0028] The Z each time independently comprises =N-, =C- or =C(R3)-, and each Z may be the same or different;

[0029] With R a The connected Z is =C-;

[0030] R a Including the structure shown in general formula (2);

[0031]

[0032] In the general formula (2), X1 includes -O-, -S- or -C(R1)(R2)-;

[0033] * is the binding site;

[0034] The R comprises a structure represented by general formula (3) or general formula (4);

[0035]

[0036] In the general formula (3), X2 represents -O-, -S-, -N(R4)- or -C(R5)(R6)-;

[0037] Z1 each time independently comprises =N-, =C- or =C(R7)-, and each Z1 may be the same or different;

[0038] Z1 connected to L1 is =C-;

[0039] The L1 and L2 independently include one of a single bond, a substituted arylene group, an unsubstituted arylene group, a substituted heteroarylene group and an unsubstituted heteroarylene group;

[0040] R1, R2, R3, R4, R5, R6, R7 and R b Independently include one of a hydrogen atom, a deuterium atom, a substituted alkyl group, an unsubstituted alkyl group, a substituted aryl group, an unsubstituted aryl group, a substituted heteroaryl group and an unsubstituted heteroaryl group.

[0041] In the present invention, the R a Including the structure shown in general formula (2);

[0042]

[0043] In the present invention, in the general formula (2), X1 includes -O-, -S- or -C(R1)(R2)-; said R1, R2 and R b independently include hydrogen atoms, deuterium atoms, substituted alkyl groups, unsubstituted alkyl groups, substituted aryl groups, unsubstituted aryl groups, substituted heteroaryl groups or unsubstituted heteroaryl groups; the alkyl groups in the substituted alkyl groups and unsubstituted alkyl groups preferably independently include C 1-10 The alkyl group of the substituted aryl group and the unsubstituted aryl group preferably independently includes one of C 6-30 The aryl group of the substituted heteroaryl group preferably independently includes one of phenyl, naphthyl, biphenyl and terphenyl; the substituted heteroaryl group or the unsubstituted heteroaryl group preferably independently includes a 5-30-membered heteroaryl group; the heteroatoms in the substituted heteroaryl group or the unsubstituted heteroaryl group preferably independently include one or more of O, S and N; the heteroaryl group in the substituted heteroaryl group and the unsubstituted heteroaryl group preferably independently includes one of naphthyridinyl, pyridinyl, dimethylfluorenyl and diphenylfluorenyl; the substituents in the substituted alkyl group, the substituted aryl group and the substituted heteroaryl group preferably independently include cyano, halogen, C 1-20 Alkyl, C 2-20 The alkenyl group, C 6-30 One or more of an aryl group and a 5- to 30-membered heteroaryl group; C 1-20 The alkyl group preferably includes one or more of methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl and adamantyl; C 6-30 The aryl group preferably includes one or more of phenyl, naphthyl, biphenyl and terphenyl; the 5-30-membered heteroaryl group preferably includes one or more of naphthyridinyl, furyl, dibenzofuranyl, carbazolyl and pyridyl.

[0044] In the present invention, R1 and R2 are preferably bonded to form a ring.

[0045] In the present invention, R includes the structure shown in general formula (3) or general formula (4);

[0046]

[0047] In the general formula (3), X2 is -O-, -S-, -N(R4)- or -C(R5)(R6)-; R4 to R6 independently include hydrogen atoms, deuterium atoms, substituted alkyl groups, unsubstituted alkyl groups, substituted aryl groups, unsubstituted aryl groups, substituted heteroaryl groups or unsubstituted heteroaryl groups; the alkyl groups in the substituted alkyl groups and unsubstituted alkyl groups preferably independently include C 1-10 The alkyl group of the substituted aryl group and the unsubstituted aryl group preferably independently includes one of C 6-30 The aryl group of the substituted heteroaryl group preferably independently includes one of phenyl, naphthyl, biphenyl and terphenyl; the substituted heteroaryl group or the unsubstituted heteroaryl group preferably includes a 5-30-membered heteroaryl group; the heteroatoms in the substituted heteroaryl group or the unsubstituted heteroaryl group preferably independently include one or more of O, S and N; the heteroaryl group in the substituted heteroaryl group or the unsubstituted heteroaryl group preferably independently includes one of naphthyridinyl, pyridinyl, dimethylfluorenyl and diphenylfluorenyl; the substituents in the substituted alkyl, substituted aryl and substituted heteroaryl group preferably independently include cyano, halogen, C 1-20 Alkyl, C 2-20 The alkenyl group, C 6-30 One or more of an aryl group and a 5- to 30-membered heteroaryl group; C 1-20 The alkyl group preferably includes one or more of methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl and adamantyl; C 6-30 The aryl group preferably includes one or more of phenyl, naphthyl, biphenyl and terphenyl; the 5-30-membered heteroaryl group preferably includes one or more of naphthyridinyl, furyl, dibenzofuranyl, carbazolyl and pyridyl.

[0048] In the present invention, the R5 and R6 are preferably bonded to form a ring;

[0049] In the present invention, the Z1 in the general formula (3) and the general formula (4) each independently includes -N- or -C(R7)-, and each Z1 may be the same or different; the R7 includes a hydrogen atom, a deuterium atom, a substituted alkyl group, an unsubstituted alkyl group, a substituted aryl group, an unsubstituted aryl group, a substituted heteroaryl group or an unsubstituted heteroaryl group; the alkyl groups in the substituted alkyl group and the unsubstituted alkyl group preferably independently include C 1-10The alkyl group of the substituted aryl group and the unsubstituted aryl group preferably independently includes one of C 6-30 The aryl group of the present invention preferably includes one of phenyl, naphthyl, biphenyl and terphenyl; the substituted heteroaryl group or the unsubstituted heteroaryl group preferably independently includes a 5-30-membered heteroaryl group; the heteroatoms in the substituted heteroaryl group or the unsubstituted heteroaryl group preferably independently include one or more of O, S and N; the heteroaryl group in the substituted heteroaryl group and the unsubstituted heteroaryl group preferably independently includes one of naphthyridinyl, pyridinyl, dimethylfluorenyl and diphenylfluorenyl; the substituents in the substituted heteroaryl group, the substituted alkyl group and the substituted aryl group preferably independently include cyano, halogen, C 1-20 Alkyl, C 2-20 The alkenyl group, C 6-30 One or more of an aryl group and a 5- to 30-membered heteroaryl group; C 1-20 The alkyl group preferably includes one or more of methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl and adamantyl; C 6-30 The aryl group preferably includes one or more of phenyl, naphthyl, biphenyl and terphenyl; the 5-30-membered heteroaryl group preferably includes one or more of naphthyridinyl, furyl, dibenzofuranyl, carbazolyl and pyridyl.

[0050] In the present invention, L1 and L2 in the general formula (3) and the general formula (4) independently include a single bond, a substituted arylene group, an unsubstituted arylene group, a substituted heteroarylene group and an unsubstituted heteroarylene group; the arylene groups in the substituted arylene group and the unsubstituted arylene group independently include C 6-30 The arylene group is preferably independently selected from phenylene, naphthylene, phenanthrylene, anthrylene, biphenylene and terphenylene; the heteroarylene groups in the substituted heteroarylene groups and the unsubstituted heteroarylene groups preferably independently select 5-30-membered heteroarylene groups, more preferably independently select pyridylene, benzofuranylene, benzothiophenylene, dimethylfluorenylene, carbazolylene, N-phenylcarbazolylene and naphthyridylene groups; the heteroatoms in the substituted heteroarylene groups and the unsubstituted heteroarylene groups preferably independently select one or more of O, S and N. The substituents in the substituted arylene groups and the substituted heteroarylene groups preferably independently select cyano, halogen, C 1-20 Alkyl, C 2-20 The alkenyl group, C 6-30 One or more of an aryl group and a 5- to 30-membered heteroaryl group; C 1-20 The alkyl group preferably includes one or more of methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl and adamantyl; C 6-30The aryl group preferably includes one or more of phenyl, naphthyl, biphenyl and terphenyl; the 5-30-membered heteroaryl group preferably includes one or more of naphthyridinyl, furyl, dibenzofuranyl, carbazolyl and pyridyl.

[0051] In the present invention, L1 and L2 preferably independently include: one of the compounds represented by formulae 3 to 6 and a single bond.

[0052]

[0053] In the present invention, the Z each time independently includes -N- or -C(R3)-, and each Z may be the same or different; the R3 includes a hydrogen atom, a deuterium atom, a substituted alkyl group, an unsubstituted alkyl group, a substituted aryl group, an unsubstituted aryl group, a substituted heteroaryl group or an unsubstituted heteroaryl group; the alkyl groups in the substituted alkyl group and the unsubstituted alkyl group preferably independently include C 1-10 The alkyl group of the substituted aryl group and the unsubstituted aryl group preferably independently includes one of C 6-30 The aryl group of the substituted heteroaryl group preferably independently includes one of phenyl, naphthyl, biphenyl and terphenyl; the substituted heteroaryl group or the unsubstituted heteroaryl group preferably independently includes a 5-30-membered heteroaryl group; the heteroatoms in the substituted heteroaryl group or the unsubstituted heteroaryl group preferably independently include one or more of O, S and N; the heteroaryl groups in the substituted heteroaryl group and the unsubstituted heteroaryl group preferably independently include one of naphthyridinyl, pyridinyl, dimethylfluorenyl and diphenylfluorenyl; the substituents in the substituted alkyl group, the substituted aryl group and the substituted heteroaryl group preferably independently include cyano, halogen, C 1-20 Alkyl, C 2-20 The alkenyl group, C 6-30 One or more of an aryl group and a 5- to 30-membered heteroaryl group; C 1-20 The alkyl group preferably includes one or more of methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl and adamantyl; C 6-30 The aryl group preferably includes one or more of phenyl, naphthyl, biphenyl and terphenyl; the 5-30-membered heteroaryl group preferably includes one or more of naphthyridinyl, furyl, dibenzofuranyl, carbazolyl and pyridyl.

[0054] In the present invention, the organic compound preferably has any one of the structures represented by general formula (II-1) to formula (II-4):

[0055]

[0056] In the present invention, the organic compound preferably has any one of the structures represented by general formula (Ш-1) to formula (Ш-12):

[0057]

[0058]

[0059]

[0060] In the present invention, the organic compound further preferably has any one of the structural formulas represented by formula (1) to formula (253):

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073] The present invention also provides a method for preparing an organic compound with a dibenzopyrone-like ring as the core as described in the above technical scheme, comprising the following steps:

[0074] The compound represented by Formula 1-1 or the compound represented by Formula 1-2 is mixed with the compound represented by Formula 3, a base, a catalyst and an organic solvent to carry out a Suzuki coupling reaction to obtain the organic compound with the dibenzopyrone-like ring as the core;

[0075]

[0076] D is a halogen atom;

[0077] RE is of formula 3; the E is -B(OH)2; the E is connected to a * site in R.

[0078] In the present invention, the molar ratio of the compound represented by Formula 1-1 or the compound represented by Formula 1-2 to the compound represented by Formula 3 is preferably 1:1.2; the molar ratio of the compound represented by Formula 1-1 or the compound represented by Formula 1-2 to the catalyst is preferably 200:1. The catalyst preferably includes one or more of Pd(PPh3)4, palladium acetate and palladium chloride;

[0079] The molar ratio of the compound represented by Formula 1-1 or the compound represented by Formula 1-2 to the base is preferably 1:2 to 3; the base preferably includes one or more of K2CO3, potassium phosphate, cesium carbonate and sodium tert-butoxide;

[0080] The mass ratio of the compound represented by Formula 1-1 or the compound represented by Formula 1-2 to the volume ratio of the organic solvent is preferably 100-600 mg:1 mL; the organic solvent preferably includes a mixed solution of toluene and ethanol or toluene; the volume ratio of toluene and ethanol in the mixed solution is preferably 2:1.

[0081] In the present invention, the Suzuki coupling reaction is preferably carried out under reflux conditions; the Suzuki coupling reaction time is preferably 48 hours; and the Suzuki coupling reaction is preferably carried out in an inert atmosphere.

[0082] After the Suzuki coupling reaction, the present invention preferably performs post-treatment on the obtained product.

[0083] The post-treatment preferably includes: cooling the product and filtering it, then removing the solvent from the obtained filtrate, and then passing the obtained crude organic compound through a column to obtain a pure organic compound.

[0084] The removal method preferably includes rotary evaporation; the column used for column filtration preferably includes a silica gel column.

[0085] The present invention also provides an organic electroluminescent device, wherein at least one functional layer of the organic electroluminescent device contains the organic compound with a dibenzopyrone-like ring as the core as described in the above technical solution or the organic compound with a dibenzopyrone-like ring as the core as prepared by the preparation method described in the above technical solution.

[0086] In the present invention, the functional layer includes one or more of a light-emitting layer, a hole blocking layer and an electron transport layer.

[0087] The present invention also provides the use of the organic electroluminescent device described in the above technical solution in a lighting element or a display element.

[0088] The following is a detailed description of the dibenzopyrone-like ring-based organic compound provided by the present invention, its preparation method and application, and the application of the organic electroluminescent device in conjunction with the embodiments, but they should not be construed as limiting the scope of protection of the present invention.

[0089] All raw materials in the examples were purchased from Yantai Wanrun Fine Chemicals Co., Ltd.

[0090] Example 1

[0091] Synthesis of compound 1

[0092]

[0093] Preparation of intermediate C-1: In a 500mL three-necked flask, add 0.1mol raw material A-1, 0.11mol raw material B-1, 0.2mol potassium carbonate, 83g water, 0.5mmol Pd(PPh3)4, 150mL toluene, 50mL anhydrous ethanol, N2 protection, heat to reflux, keep the reaction for 6h, cool to 25℃, separate the liquids, collect the organic phase, wash with water until neutral, remove the solvent from the organic phase under reduced pressure to obtain crude intermediate C-1.

[0094] In a 500mL three-necked flask, add crude intermediate C-1 containing 0.1mol intermediate C-1, 0.3mol sodium hydroxide, 200mL anhydrous ethanol, N2 protection, heat to reflux, keep warm for 6h, cool to 25°C, add 10% dilute hydrochloric acid solution dropwise, stir for 0.5h, extract with ethyl acetate, pass the organic phase through a silica gel column, remove the solvent under reduced pressure to obtain a less refined intermediate C-1, recrystallize from toluene, filter and dry to obtain intermediate C-1 (C 26 H 17 BrO3).

[0095] Elemental analysis of intermediate C-1: C, 68.29; H, 3.75; Br, 17.47; Measured value: C, 68.33; H, 3.77; Br, 17.42.

[0096] LC-MS analysis of intermediate C-1: theoretical value: 456.04, found value: 457.08 ([M+H] + ).

[0097] Preparation of intermediate D-1: In a 1L three-necked flask, add 0.2mol intermediate C-1, 740g methanesulfonic acid, N2 protection, heat to 70-75°C, keep warm for 4h, cool to 25°C, slowly introduce the reaction solution into 200g crushed ice, stir, filter, rinse with 50mL water to obtain crude intermediate D-1, recrystallize from toluene, filter, and dry to obtain intermediate D-1 (C 25 H13BrO3).

[0098] Elemental analysis of intermediate D-1: theoretical value: C, 68.05; H, 2.97; Br, 18.11; tested value: C, 68.08; H, 2.90; Br, 18.20.

[0099] LC-MS analysis of intermediate D-1: theoretical value: 440.00, found value: 441.01 ([M+H] + ).

[0100] Preparation of compound 1: In a 500 mL three-necked flask, add 0.1 mol of intermediate D-1 and 0.12 mol of raw material E-1 to 250 mL of a mixed solvent of toluene:ethanol = 2:1, add 0.2 mol of potassium carbonate, add 0.5 mmol Pd(PPh3)4 after deoxygenation, reflux for 48 hours under a nitrogen atmosphere, take a sample point plate, and after the reactants react completely, cool and filter, and evaporate the filtrate to remove the solvent. The crude product is passed through a silica gel column to obtain compound 1.

[0101] Embodiments 2 to 20

[0102] The only difference from Example 1 is that raw material B and raw material E are different.

[0103] The test results of the raw materials B and E used in Examples 1 to 20 and the compounds obtained in Examples 1 to 20 are shown in Table 1.

[0104] Table 1 Test results of raw materials B and E used in Examples 1 to 20 and compounds obtained in Examples 1 to 20

[0105]

[0106]

[0107]

[0108] The H NMR spectra of the compounds obtained in Examples 1 to 20 were tested, and the results are shown in Table 2.

[0109] Table 2 H NMR spectrum data of compounds obtained in Examples 1 to 20

[0110]

[0111]

[0112]

[0113] Comparative application example 1

[0114] a) The substrate layer 1 is transparent glass, and an anode layer 2 (Ag, thickness of 100 nm) is deposited on the surface of the substrate layer 1 by vacuum evaporation;

[0115] b) on the anode layer 2, HAT-CN is deposited by vacuum evaporation with a thickness of 10 nm as the hole injection layer 3;

[0116] c) HT-1 was deposited on the hole injection layer 3 by vacuum evaporation to a thickness of 140 nm as the hole transport layer 4;

[0117] d) On the hole transport layer 4, EB-1 is deposited by vacuum evaporation to a thickness of 30 nm as the electron blocking layer 5,

[0118] e) evaporating a light-emitting layer 6 on the electron blocking layer 5, wherein GH-2 and D1 are used as the main materials, GD-1 is used as the doping material, the mass ratio of GH-2, D1 and GD-1 is 45:45:10, and the thickness is 40 nm;

[0119] f) on the light-emitting layer 6, ET-1 and Liq are evaporated by vacuum evaporation in a mass ratio of 1:1 with a thickness of 40 nm to serve as an electron transport layer 7;

[0120] g) on ​​the electron transport layer 7, vacuum evaporate LiF with a thickness of 1 nm to serve as the electron injection layer 8;

[0121] h) On the electron injection layer 8, a Mg:Ag layer with a mass ratio of 1:9 and a thickness of 15 nm is vacuum-deposited as the cathode layer 9;

[0122] i) Alq3 was deposited on the cathode layer 9 by vacuum deposition to a thickness of 70 nm to serve as the light extraction layer 10 .

[0123] Comparative Application Example 1 The structure of the device is as follows Figure 1 As shown: 1-substrate layer, 2-anode layer, 3-hole injection layer, 4-hole transport layer, 5-electron blocking layer, 6-light-emitting layer, 7-electron transport layer, 8-electron injection layer, 9-cathode layer, 10-light extraction layer

[0124] Application Examples 1 to 20, Comparative Application Examples 2 to 3

[0125] The only difference between Application Examples 1 to 20 and Comparative Application Examples 2 to 3 and Comparative Application Example 1 is the composition of the light-emitting layer. The composition of the light-emitting layer of Application Examples 1 to 20 and Comparative Application Examples 2 to 3 is shown in Table 3.

[0126] The molecular structure formula of the relevant materials is shown below:

[0127]

[0128] Table 3 Composition (mass ratio) of the light-emitting layer of application examples 1 to 20 and comparative application examples 1 to 3

[0129]

[0130]

[0131] The current efficiency and life of the devices obtained in Application Examples 1 to 20 and Comparative Application Examples 1 to 3 were measured, and the results are shown in Table 4.

[0132] Table 4 Measurement results of current efficiency and life of devices obtained in Application Examples 1 to 20 and Comparative Application Examples 1 to 3

[0133]

[0134]

[0135] Note: The current efficiency is tested using the IVL (current-voltage-luminance) test system, and the current density during the test is 10mA / cm 2 .

[0136] From the results in Table 4, it can be seen that the organic compound of the present invention, as one of the dual hosts of the light-emitting layer, has significantly improved device efficiency and device life compared with comparative application examples 1 to 3.

[0137] The above is only a preferred embodiment of the present invention. It should be pointed out that for ordinary technicians in this technical field, several improvements and modifications can be made without departing from the principle of the present invention. These improvements and modifications should also be regarded as the scope of protection of the present invention.

Claims

1. An organic compound with a dibenzopyrone ring as the core, characterized in that: It has a structure represented by general formula (1.1) or general formula (1.2): The Z each time independently comprises =N-, =C- or =C(R3)-, and each Z may be the same or different; With R a The connected Z is =C-; R a Including the structure shown in general formula (2); In the general formula (2), X1 includes -O-, -S- or -C(R1)(R2)-; * is the binding site; The R comprises a structure represented by general formula (3) or general formula (4); In the general formula (3), X2 represents -O-, -S-, -N(R4)- or -C(R5)(R6)-; Z1 each time independently comprises =N-, =C- or =C(R7)-, and each Z1 may be the same or different; Z1 connected to L1 is =C-; The L1 and L2 independently include one of a single bond, a substituted arylene group, an unsubstituted arylene group, a substituted heteroarylene group and an unsubstituted heteroarylene group; R1, R2, R3, R4, R5, R6, R7 and R b Independently include one of a hydrogen atom, a deuterium atom, a substituted alkyl group, an unsubstituted alkyl group, a substituted aryl group, an unsubstituted aryl group, a substituted heteroaryl group and an unsubstituted heteroaryl group.

2. The organic compound according to claim 1, characterized in that It has any one of the structures represented by general formula (II-1) to formula (II-4):

3. The organic compound according to claim 1, characterized in that It has any one of the structures represented by general formula (Ш-1) to formula (Ш-12):

4. The organic compound according to claim 1, characterized in that It has any one of the structures shown in formula (1) to formula (253):

5. The organic compound according to claim 1, characterized in that The substituents in the substituted arylene group, substituted aryl group and substituted heteroaryl group independently include halogen atoms, cyano groups, C1-C 20 Alkyl, C 2～20 Alkenyl, C6~C 30 One or more of an aryl group and a 5- to 30-membered heteroaryl group containing one or more heteroatoms.

6. The organic compound according to claim 1, characterized in that The heteroatoms in the substituted heteroarylene group, the unsubstituted heteroarylene group, the substituted heteroaryl group and the unsubstituted heteroaryl group independently include one or more of O, S and N.

7. The organic compound according to claim 1, characterized in that The arylene groups in the substituted arylene group and the unsubstituted arylene group independently include C 6-30 One of the arylene groups; The heteroarylene groups in the substituted heteroarylene groups and the unsubstituted heteroarylene groups independently include one of 5- to 30-membered heteroarylene groups; The substituted alkyl and unsubstituted alkyl independently include C 1-10 One of the alkyl groups; The aryl groups in the substituted aryl group and the unsubstituted aryl group independently include C 6-30 One of the aromatic groups; The heteroaryl groups in the substituted heteroaryl group and the unsubstituted heteroaryl group independently include one of 5- to 30-membered heteroaryl groups.

8. The method for preparing an organic compound with a dibenzopyrone-like ring as the core according to any one of claims 1 to 7, characterized in that: The following steps are involved: The compound represented by Formula 1-1 or the compound represented by Formula 1-2 is mixed with the compound represented by Formula 3, a base, a catalyst and an organic solvent to carry out a Suzuki coupling reaction to obtain the organic compound with the dibenzopyrone-like ring as the core; D is a halogen atom; RE is of formula 3; the E is -B(OH)2; the E is connected to a * site in R.

9. An organic electroluminescent device, characterized in that: At least one functional layer in the organic electroluminescent device contains the organic compound with a dibenzopyrone-like ring as the core as described in any one of claims 1 to 7 or the organic compound with a dibenzopyrone-like ring as the core prepared by the preparation method described in claim 8; the functional layer includes a light-emitting layer, a hole blocking layer and an electron transport layer.

10. Use of the organic electroluminescent device according to claim 9 in a lighting element or a display element.

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