An amine-based compound having a benzophenanthrofuranyl group and an organic light emitting device

Abstract

This invention discloses an amino compound with a benzophenanthrene furan group and an organic light-emitting device, selected from compounds of formula 1: Al-A 10 One of the groups is derived from Formula 2, where * represents a bond connected to the basic skeleton in Formula 1. When A2 is derived from a group in Formula 2, L1 is a para-phenylene group, R1 and R2 are derived from single bonds, substituted or unsubstituted C5-C24 aromatic hydrocarbon groups, substituted or unsubstituted C5-C24 heteroaromatic hydrocarbon groups, and Ar1 and Ar2 are derived from C5-C30 aromatic hydrocarbon groups, substituted or unsubstituted C5-C30 heteroaromatic hydrocarbon groups. In this invention, the triarylamine is para-linked to a transition benzene ring with benzo[a]phenanthrenefuran. This benzene ring linkage enhances the overall stability of the target molecule, strengthens the conjugation of the molecule, and increases the stacking property of the molecule in organic light-emitting materials. This invention also sets phenanthrene, naphthyl, or dibenzothiophene groups on the other two substituents of the triarylamine, affecting the electron affinity and electron transport properties of the triarylamine and further extending its lifespan.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescence technology, and more specifically to an organic light-emitting device based on an amine compound with a benzo[phenanthrene]furan group. Background Technology

[0002] Organic light-emitting devices (OLEDs) are light-emitting devices that utilize the following principle: when an electric field is applied, fluorescent materials emit light through the recombination of holes injected at the positive electrode and electrons injected at the negative electrode. These self-emissive devices possess characteristics such as low voltage, high brightness, wide viewing angle, fast response, and good temperature adaptability. Furthermore, they are ultra-thin and can be fabricated on flexible panels, making them widely used in mobile phones, tablets, televisions, lighting, and other fields.

[0003] Organic electroluminescent devices (OLEDs) have a sandwich-like structure, consisting of electrode material layers and organic functional materials sandwiched between them. These various functional materials are stacked together according to their intended use to form the OLED. As a current-carrying device, when a voltage is applied to the two electrodes of the OLED, positive and negative charges are generated in the organic functional material layers through the action of an electric field. These positive and negative charges then recombine in the light-emitting layer, producing light; this process is called electroluminescence.

[0004] Triarylamines are common organic electroluminescent materials. By selecting benzo[a]phenanthrene-furan group as a substituent on the triarylamine and applying this compound to organic light-emitting materials, the properties of this group can be utilized to improve some characteristics of the material and enhance the product's performance parameters. For example, this is illustrated in publication number CN 115956073. Patent application A discloses materials for organic electroluminescent devices. The patent discloses triarylamine compounds with a benzo[a]phenanthrene-furan group, and provides a specific structural formula showing the direct connection of the triarylamine compound to the benzo[a]phenanthrene-furan. The other two groups of the triarylamine are selected from substituents of benzene, biphenyl, dimethylfluorene, and spirodifluorene. The patent application also discloses compounds in which the triarylamine is connected to the benzo[a]phenanthrene-furan group via a transition group on the benzene ring. When the transition group is attached to the 2-position of the benzo[a]phenanthrene-furan, the triarylamine and benzo[a]phenanthrene-furan are attached to the benzene ring of the transition group at either the ortho or meta position. Applying these compounds to devices shows a significant advantage in OLED lifetime, with other OLED performance data being roughly equivalent. However, lifetime is only one parameter of OLED device performance and has a relatively small impact on improving overall OLED device performance. Therefore, it is necessary to develop higher-performance organic electroluminescent materials based on the triarylamine structure. Summary of the Invention

[0005] The purpose of this invention is to address the aforementioned technical problems by providing an amino compound containing a benzo[phenanthrene]furan group, selected from compounds of Formula 1:

[0006]

[0007] A1-A 10 One of them is a group derived from Formula 2, where * represents a bond connected to the basic skeleton in Formula 1.

[0008]

[0009] When A1, A3-A 10 When one of the groups is taken from Formula 2, L1, R1, and R2 are taken from single bonds, substituted or unsubstituted C5-C24 aromatic hydrocarbon groups, substituted or unsubstituted C5-C24 heteroaromatic hydrocarbon groups, and Ar1 and Ar2 are taken from C5-C30 aromatic hydrocarbon groups, substituted or unsubstituted C5-C30 heteroaromatic hydrocarbon groups, and at least one of Ar1 and Ar2 is selected from: substituted or unsubstituted phenanthrene, naphthyl, and dibenzothiophene.

[0010] When A2 is taken from a group of Formula 2, L1, R1, and R2 are taken from a single bond, a substituted or unsubstituted C5-C24 aromatic hydrocarbon group, a substituted or unsubstituted C5-C24 heteroaromatic hydrocarbon group, and L1 is not para-phenylene, Ar1 and Ar2 are taken from a C5-C30 aromatic hydrocarbon group, a substituted or unsubstituted C5-C30 heteroaromatic hydrocarbon group, and at least one of Ar1 and Ar2 is selected from: substituted or unsubstituted phenanthrene, naphthyl, or dibenzothiophene.

[0011] When A2 is taken from a group of Formula 2, L1 is a para-phenylene, R1 and R2 are taken from a single bond, a substituted or unsubstituted C5-C24 aromatic hydrocarbon group, or a substituted or unsubstituted C5-C24 heteroaromatic hydrocarbon group, and Ar1 and Ar2 are taken from a C5-C30 aromatic hydrocarbon group or a substituted or unsubstituted C5-C30 heteroaromatic hydrocarbon group.

[0012] As a preferred embodiment of the present invention, A1, A3-A 10 One of the groups is derived from Formula 2, where L1, R1, and R2 are each independently selected from single-bonded, substituted, or unsubstituted phenyl groups; Ar1 ​​is selected from substituted or unsubstituted phenanthrene, naphthyl, or dibenzothiophene; and Ar2 is selected from substituted or unsubstituted phenyl groups, naphthyl, anthracene, phenanthrene, fluorenyl, oxofluorenyl, 9,9-spirodifluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, carbazolyl, N-ethylcarbazolyl, 4-hydroxycarbazolyl, benzocarbazolyl, benzothiophene, furanyl, thiophene, phenylpyrimidinyl, pyrimidinyl, pyridinyl, or triazineyl.

[0013] In a preferred embodiment of the present invention, A2 is derived from a group of Formula 2, L1, R1, and R2 are each independently selected from single-bonded, substituted, or unsubstituted phenyl groups, and L1 is not para-phenylene. Ar1 is selected from substituted or unsubstituted phenanthrene, naphthyl, or dibenzothiophene group; Ar2 is selected from substituted or unsubstituted phenyl, naphthyl, anthracene, phenanthrene, fluorenyl, oxofluorenyl, 9,9-spirodifluorenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, carbazolyl, N-ethylcarbazolyl, 4-hydroxycarbazolyl, benzocarbazolyl, benzothiophene, furanyl, thiophene, phenylpyrimidinyl, pyrimidinyl, pyridinyl, or triazineyl.

[0014] In a preferred embodiment of the present invention, A2 is derived from a group of Formula 2, L1 is a para-phenylene group, R1 and R2 are derived from single bonds, substituted or unsubstituted C5-C24 aromatic hydrocarbon groups, substituted or unsubstituted C5-C24 heteroaromatic hydrocarbon groups, and Ar1 and Ar2 are each individually selected from the following groups:

[0015]

[0016]

[0017] As a preferred embodiment of the present invention, the substituent is selected from at least one of the following atoms or groups: deuterium, hydroxyl, cyano, monodeuterylmethyl, dideuterylmethyl, trideuterylmethyl, C1-C4 straight-chain or branched alkyl, C6-C18 aromatic hydrocarbon group, and C5-C24 heteroaromatic hydrocarbon group.

[0018] In a preferred embodiment of the present invention, A2 is derived from a group of Formula 2, L1 is a para-phenylene group, and the amino compound containing a benzo[a]phenanthrofuran group is one of the following structural formulas:

[0019]

[0020]

[0021]

[0022]

[0023]

[0024]

[0025]

[0026]

[0027]

[0028]

[0029]

[0030]

[0031]

[0032]

[0033]

[0034] In a preferred embodiment of the present invention, A2 is derived from a group of Formula 2, L1 is selected from a single bond, and the amino compound containing a benzo[phenanthrene]furan group is one of the following structural formulas:

[0035]

[0036]

[0037] As a preferred embodiment of the present invention, A1, A3-A 10 One of the groups is derived from Formula 2, L1 is selected from a single bond, and the amino compound containing a benzo[phenanthrene]furan group is one of the following structural formulas:

[0038]

[0039]

[0040] An organic electroluminescent device includes a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, said organic layer containing an amine compound having a benzophenanthrene furan group as described in any one of claims 1-8.

[0041] As a preferred embodiment of the present invention, the organic layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer; at least one of the hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, and electron injection layer contains the above-mentioned organic electroluminescent compound.

[0042] As a preferred embodiment of the present invention, the electron blocking layer contains the aforementioned organic electroluminescent compound.

[0043] The synthetic route for the compound of the present invention having the structure shown in Formula 1 is as follows:

[0044]

[0045] The beneficial effects of this invention are:

[0046] The triarylamine of this invention is linked to the 2-position of benzo[a]phenanthrenefuran via a benzene ring transition, and the triarylamine and benzo[a]phenanthrenefuran are para-linked to the transition benzene ring. This benzene ring linkage enhances the overall stability of the target molecule, while the para-linked benzene ring enhances the molecule's conjugation. This conjugation helps regulate the molecule's electronic structure, influencing its photoelectric properties; conjugation is a crucial factor in achieving specific electronic properties. The para-linked benzene ring makes the molecule more flattened, which may contribute to increased molecular stacking in organic light-emitting materials, thereby affecting the material's crystal structure and properties, especially charge transport properties in organic semiconductors. The para-linked benzene ring in this compound also produces a certain steric hindrance effect, affecting the product's stereoconfiguration and intermolecular interactions.

[0047] The invention of benzene involves setting phenanthrene, naphthyl, or dibenzothiophene groups on two additional substituents of triarylamines, affecting the electron affinity and electron transport properties of the triarylamines. This results in better electron transport performance, which is beneficial for their use as electron transport materials in organic electronic devices. These substituents also affect the absorption spectral characteristics, which is beneficial for the design and performance optimization of optoelectronic devices. Furthermore, these substituents enhance the stability of the triarylamine molecule, reducing its decomposition or degradation during application, thereby further extending its lifespan. Attached Figure Description

[0048] Figure 1 This is a schematic diagram of the structure of the organic electroluminescent device provided by the present invention;

[0049] The numbers in the diagram represent: 1-anode, 2-hole injection layer, 3-hole transport layer, 4-electron blocking layer, 5-light emitting layer, 6-hole blocking layer, 7-electron transport layer, 8-electron injection layer, and 9-cathode.

[0050] Figure 2 This is the HPLC chromatogram of compound 104 of the present invention.

[0051] Figure 3 The DSC spectrum of compound 104 of this invention is shown below. Figure 3 It can be seen that the Tg value of compound 104 is 147.43℃.

[0052] Figure 4 The TGA spectrum of compound 104 of this invention is shown below. Figure 4 It can be seen that the thermal weight loss temperature Td of compound 100 is 500.90℃. Detailed Implementation

[0053] Embodiments of various aspects are further illustrated and described below. It should be understood that the description herein is not intended to limit the claims to the specific aspects described. Rather, it is intended to cover substitutions, modifications, and equivalents that may be included within the spirit and scope of this disclosure as defined by the appended claims.

[0054] As used herein, in the terms “deuterated” and “undeuterated,” the term “deuterated” means that at least one hydrogen in the group is recoordinated with deuterium. The term “undeuterated” means that none of the hydrogens in the group are recoordinated with deuterium.

[0055] In this document, "aromatic group," "aryl," or "aromatic group" refers to a group containing one or more aromatic rings, including but not limited to benzene, naphthalene, phenanthrene, fluorene, acenaphthene, pyridine, pyrrole, furan, thiophene, etc. In C6-C30 aromatic groups, C6-C30 means that the group contains 6-30 carbon atoms. In C1-C10 alkyl-substituted C6-C20 aromatic groups, C1-C10 refers to the number of carbon atoms in the substituent, and C6-C20 refers to the number of carbon atoms in the unsubstituent aromatic group. Aromatic groups can be divided into monocyclic aryl and polycyclic aryl groups. Specific aromatic groups in this invention include, but are not limited to, phenyl, biphenyl, terphenyl, anthracene, naphthyl, phenanthrene, fluorenyl, dibenzofuranyl, dibenzothiophene, 9,9-spirodifluorenyl, 9,9-dimethylfluorenyl, or 9,9-diphenylfluorenyl, etc. Aromatic groups can be substituted or unsubstituted.

[0056] As used herein, "cycloalkyl" refers to a monocyclic or fused ring group consisting entirely of carbon atoms (a "fused" ring means that each ring in the system shares an adjacent pair of carbon atoms with other rings in the system), wherein one or more rings are saturated alicyclic rings, generally having 3-20 carbon atoms, preferably 3-12 carbon atoms, and more preferably 3-10 carbon atoms. Cycloalkyl groups can be classified into monocyclic alkyl groups having only one ring and fused alkyl groups having multiple rings. Examples of monocyclic alkyl groups include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, and cycloheptane. Cycloalkyl groups can be substituted or unsubstituted.

[0057] As used herein, "cycloalkenyl" refers to a monocyclic or fused ring group consisting entirely of carbon (a "fused" ring means that each ring in the system shares a pair of adjacent carbon atoms with other rings in the system), wherein one or more rings do not have a fully connected π-electron system and contain at least one alkenyl group, which generally has 3-20 carbon atoms, preferably 3-12 carbon atoms, more preferably 3-10 carbon atoms. Examples of cycloalkenyl groups include, but are not limited to, cyclopentene, cyclohexene, cyclohexadiene, and cycloheptanetriene. The cycloalkenyl group can be substituted or unsubstituted.

[0058] In this article, "deuterated aromatic group" refers to an aromatic group in which one or more hydrogen atoms are replaced by deuterium.

[0059] In this article, "deuterated phenyl" refers to a group in which one or more hydrogen atoms in a phenyl group are replaced by deuterium.

[0060] In this article, "heteroaryl" refers to a heteroaryl group obtained by replacing one or more C atoms in the structure of "aryl" with one or more heteroatoms (such as N, O or S).

[0061] Unless otherwise specified in the examples, the procedures should be performed under standard conditions or conditions recommended by the manufacturer. Reagents or instruments whose manufacturers are not specified are all commercially available products.

[0062] Example 1:

[0063] Compound 104:

[0064]

[0065] Compound 104 was prepared according to the following method:

[0066] Scheme 104-ZJ1 Procedure: In a 2L three-necked flask, add 104-SM1 (250g, 0.89mol, 1eq), pinacol diborate (293.2g, 1.154mol, 1.3eq), potassium acetate (261g, 2.664mol, 3eq), PdCl2 (dppf) (13g, 17.76mmol, 0.02eq), and 1,4-dioxane (1500ml). Under N2 protection, heat to 90-100℃ and stir the reaction. HPLC monitoring showed that 104-SM1 ≤ 0.5%.

[0067] Post-processing: Stop the reaction, filter the solution through silica gel while hot, wash the filter cake with 600 ml of DCM, concentrate the filtrate to dryness under reduced pressure, add 250 ml of ethanol, cool and stir to precipitate crystals, filter, and dry the filter cake at 85°C with forced air to obtain 197.2 g of gray solid, yield 67.6%.

[0068] Scheme 104-ZJ2

[0069] Procedure: In a 3L three-necked flask, add 104-ZJ1 (197.2g, 0.6mol, 1eq), 104-SM2 (103.3g, 0.6mol, 1eq), potassium carbonate (166g, 1.2mol, 2eq), Pd(PPd3)4 (13.9g, 12mmol, 0.02eq), and toluene / ethanol / water (1600ml + 800ml + 480ml). Under N2 protection, heat to reflux and react. Monitor with HPLC until 104-ZJ1 ≤ 0.5%.

[0070] Post-processing: Stop the reaction, stir and separate the liquids, extract with DCM in the aqueous phase, combine the organic phases, filter through silica gel powder, concentrate the filtrate to dryness under reduced pressure, and use it directly in the next reaction without purification.

[0071] Solution 104-ZJ3

[0072] Procedure: Add 104-ZJ2 (theoretical 176.3g, 0.6mol, 1eq) and acetic acid (1500ml) to a 3L three-necked flask and cool to below 10℃. Add concentrated sulfuric acid (212ml) dropwise. After the addition is complete, keep warm and stir for 30min. Cool to 0-10℃ and add an aqueous solution of sodium nitrite (82.5g, 1.2mol, 2eq) (150ml) dropwise. After the addition is complete, heat to 115℃ and stir to react overnight.

[0073] Post-processing: Stop heating, cool to room temperature, filter, rinse the filter cake with water, dissolve the filter cake with DCM, filter again, remove insoluble matter, add PE to the filtrate, concentrate under reduced pressure to remove most of the solvent, filter again, and dry the filter cake at 85°C with forced air to obtain 35.7g of brownish-yellow solid, with a two-step yield of 21.5%.

[0074] Solution 104-ZJ4

[0075] Procedure: In a 500 ml three-necked flask, 104-ZJ3 (25 g, 90.3 mmol, 1 eq), pinacol diboronate (29.8 g, 0.117 mol, 1.3 eq), potassium acetate (26.6 g, 0.271 mol, 3 eq), XPhos (2.58 g, 5.42 mmol, 0.06 eq), Pd2(dba)3 (2.48 g, 2.71 mmol, 0.03 eq) and 1,4-dioxane (300 ml) were added. Under N2 protection, the mixture was heated to 90–100 °C and stirred. The 104-ZJ3 concentration was monitored by HPLC to be ≤0.5%.

[0076] Post-processing: Stop the reaction, filter the mixture through silica gel while hot, wash the filter cake with 300 ml of DCM, concentrate under reduced pressure to dryness, add 100 ml of ethanol to crystallize, filter, and dry the filter cake at 85°C with forced air to obtain 33.2 g of gray solid, yield 99.7%.

[0077] Solution 104-ZJ5

[0078] Procedure: In a 2L three-necked flask, add 104-ZJ4 (33.2g, 90.2mmol, 1eq), 104-SM3 (26.8g, 94.7mmol, 1.05eq), potassium carbonate (24.9g, 0.18mol, 2eq), Pd(PPd3)4 (2.08g, 1.804mmol, 0.02eq), and toluene / ethanol / water (600ml + 300ml + 180ml). Under N2 protection, heat to reflux and react. Monitor with HPLC until 104-ZJ4 ≤ 0.5%.

[0079] Post-processing: Stop the reaction, add 1L of ethanol, cool and stir to induce crystallization, filter, wash the filter cake with water and ethanol, and dry the filter cake at 85℃ to obtain 24.3g of gray solid, yield 67.8%.

[0080] Option 104

[0081] Procedure: 104-ZJ5 (24.3 g, 61.2 mmol, 1 eq), 104-SM4 (21.14 g, 61.2 mmol, 1 eq), sodium tert-butoxide (7.06 g, 73.44 mol, 1.2 eq), tri-tert-butylphosphine (5 mL, 2.448 mmol, 0.04 eq), and toluene (250 mL) were added to a 500 mL three-necked flask. Under nitrogen protection, Pd2(dba)3 (1.12 g, 1.224 mmol, 0.02 eq) was added, and the mixture was heated to 110 °C and stirred. HPLC monitoring showed that CP8470-ZJ5 ≤ 0.5%.

[0082] Post-processing: Stop the reaction, add water, stir and separate the liquid, extract with DCM in the aqueous phase, combine the organic phases, add 20g of 100-200 mesh silica gel to make sand, pack 300g of 100-200 mesh silica gel into a column, perform column chromatography, PE / DCM = 20 / 1~10 / 1~5 / 1~3 / 1, collect the product spot, concentrate under reduced pressure to dryness, add 50ml of ethanol to the sample and hot-purge overnight, filter, recrystallize the filter cake 8 times with toluene / ethanol, dry the filter cake at 85℃ with forced air to obtain 5.6g of off-white solid with a purity of 99.8670% and a yield of 13.8%.

[0083] Compounds 2, 4, 5, 6, 7, 8, 9, 11, 13, 15, 17, 18, 19, 21, 25, 27, 34, 35, 40, 41, 51, 53, 54, 55, 89, 90, 99, 100, 106, 110, 111, 107, 126, 127, 129, 131, 171, 172, 174, 175, 179, 182, 190, 191, 215, 216, 222, 223, 225, 226, 249, and 250 were obtained by similar methods. See Table 1 below for details.

[0084] Table 1

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099] Example 54:

[0100] Compound 271:

[0101]

[0102] Compound 271 was prepared according to the following method:

[0103] Scheme 271-ZJ1

[0104] For post-processing, see 104-ZJ1.

[0105] Scheme 271-ZJ2 Post-processing 104-ZJ2.

[0106] Solution 271-ZJ3 For post-processing, see 104-ZJ3.

[0107] Option 271

[0108] For post-processing, see section 104. Yield: 63.7%.

[0109] Compounds 272, 273, 274, 285, and 286 were obtained using a similar method; see Table 2 below for details.

[0110]

[0111]

[0112] Example 60: Compound 300:

[0113]

[0114] Compound 300 was prepared according to the following method:

[0115] Solution 300-ZJ1 For post-processing, see 104-ZJ1.

[0116] Solution 300-ZJ2 Post-processing 104-ZJ2.

[0117] Solution 300-ZJ3 For post-processing, see 104-ZJ3.

[0118] Option 300 Post-processing is described in section 104; yield was 57.9%.

[0119] Compounds 301, 302, 303, 315, and 311 were obtained using similar methods, as detailed in Table 3 below.

[0120]

[0121]

[0122] The results of the synthesis and identification of the compounds prepared in Tables 1-3 above are shown in Table 4 below:

[0123] Table 4

[0124]

[0125]

[0126] Material property testing:

[0127] The compounds of this invention were tested as follows: 104, 2, 4, 5, 6, 7, 8, 9, 11, 13, 15, 17, 18, 19, 21, 25, 27, 34, 35, 40, 41, 51, 53, 54, 55, 89, 90, 99, 100, 106, 110, 111, 107, 126, 127, 129, 131, 171, 172, 1 The thermogravimetric temperature Td and glass transition temperature Tg of 74, 175, 179, 182, 190, 191, 215, 216, 222, 223, 225, 226, 249, 250, 271, 272, 273, 274, 285, 286, 300, 301, 302, 303, 315, and 311 are shown in Table 5 below.

[0128] Note: The thermogravimetric temperature Td is the temperature at which 5% weight is lost in a nitrogen atmosphere. It was measured on a TGAN-1000 thermogravimetric analyzer with a nitrogen flow rate of 10 mL / min. Tg (glass transition temperature) was measured by differential scanning calorimetry (DSC, Shinco DSC N-650) at a heating rate of 10 °C / min.

[0129] Table 5:

[0130]

[0131]

[0132] As can be seen from the above data, the compounds synthesized in this invention have excellent thermal stability and all have high Td values, indicating that compounds conforming to the general structural formula of this invention have excellent thermal stability and can well meet the requirements for the use of organic electroluminescent materials.

[0133] Device performance testing:

[0134] Application Example 1:

[0135] ITO was used as the anode substrate material for the reflective layer, and its surface was treated sequentially with water, acetone, and N2 ions.

[0136] A 10 nm thick HT-1 layer containing 3 wt% NDP-9 is deposited on top of the ITO anode substrate to form a hole injection layer (HIL).

[0137] A hole transport layer (HTL) is formed by depositing 100 nm of HT-1 above the hole injection layer (HIL);

[0138] The organic electroluminescent compound 104 prepared in Example 1 of the present invention was vacuum evaporated over the hole transport layer (HTL) to form an electron blocking layer (BP) with a thickness of 10 nm.

[0139] BH-1 was used as the main blue light material and BD-1 was used as the blue light dopant (the amount of BD-1 was 3% of the weight of ADN). They were evaporated at different rates on the hole transport layer (HTL) to form a light-emitting layer with a thickness of 20 nm.

[0140] HB-1 was deposited onto the light-emitting layer to obtain a hole blocking layer (HBL) with a thickness of 20 nm;

[0141] ET-1 was deposited as an electron transport layer material (ET) onto a hole blocking layer (HBL) to obtain an electron transport layer (ETL) with a thickness of 30 nm. An electron injection layer (EIL) with a thickness of 2 nm was deposited on top of the electron transport layer (ETL).

[0142] Subsequently, magnesium (Mg) and silver (Ag) were mixed in a 9:1 ratio and vapor-deposited to obtain a cathode with a thickness of 15 nm. A 50 nm thick DNTPD was then deposited on the cathode sealing layer. In addition, the cathode surface was sealed with a UV-curable adhesive and a sealing cap containing a desiccant to protect the organic electroluminescent device from the influence of atmospheric oxygen or moisture. Thus, an organic electroluminescent device was prepared.

[0143]

[0144] Application Example 2-53

[0145] Organic electroluminescent devices of Application Examples 2-53 were fabricated using compounds 2, 4, 5, 6, 7, 8, 9, 11, 13, 15, 17, 18, 19, 21, 25, 27, 34, 35, 40, 41, 51, 53, 54, 55, 89, 90, 99, 100, 106, 110, 111, 107, 126, 127, 129, 131, 171, 172, 174, 175, 179, 182, 190, 191, 215, 216, 222, 223, 225, 226, 249, and 250 of the present invention as BPs, with the other parts being the same as in Application Example 1.

[0146] Compare with Examples 1-8:

[0147] The difference from Application Example 1 is that compounds P4c, P3b, P2a, P1c, 123-12, 123-13, 123-14, and 123-15 from CN115956073A are used instead of compound 104 in this application as BP, while the rest is the same as Application Example 1.

[0148] The organic electroluminescent device manufactured in the above application example and the organic electroluminescent device manufactured in the comparative example have the characteristic of operating at a current density of 10 mA / cm². 2 The results were measured under the specified conditions and are shown in Table 6.

[0149] Table 6:

[0150]

[0151]

[0152] As shown in Table 6 above, when the compound of the present invention is used as BP in blue organic electroluminescent devices, the luminous efficiency is significantly improved at the same current density, the device start-up voltage is reduced, and the power consumption of the device is relatively reduced.

[0153] The organic electroluminescent devices prepared in Comparative Examples 1-8 and Application Examples 1-5, 12, 13, 18, 19, 30, 33, 34, 35, 40, 41, 44, 45, 50, and 51 were subjected to luminescence lifetime tests to obtain the luminescence lifetime T97% data (the time for the luminous brightness to decrease to 97% of the initial brightness). The testing equipment was a TEO luminescent device lifetime testing system. The results are shown in Table 7.

[0154] Table 7:

[0155]

[0156]

[0157] As shown in Table 7 above, when the compound of the present invention is used as BP in organic electroluminescent devices, the lifespan of the prepared organic electroluminescent devices is further improved, so it has a very broad application prospect.

[0158] Application Example 54:

[0159] ITO was used as the anode substrate material for the reflective layer, and its surface was treated sequentially with water, acetone, and N2 ions.

[0160] A hole injection layer (HIL) is formed by depositing 10 nm of HT-1 doped with 2% NDP-9 by mass on top of the ITO anode substrate.

[0161] A first hole transport layer (HTL) is formed by depositing 100 nm of HT-1 above the hole injection layer (HIL);

[0162] Compound 271 designed in this invention was vacuum-deposited over the first hole transport layer (HTL) to form a second hole transport layer (GPL) with a thickness of 30 nm.

[0163] Compounds G1 and G2 were co-deposited as green light host materials in a 5:5 mass ratio, and GD-1 was deposited as a dopant material (GD-1 amount was 8% of the total mass of G1 and G2) on the second hole transport layer (GPL) to form a light-emitting layer with a thickness of 30 nm.

[0164] HB-1 was deposited onto the light-emitting layer to obtain a hole blocking layer (HBL) with a thickness of 20 nm;

[0165] ET-1 and LiQ were co-deposited onto the hole blocking layer (HBL) at a mass ratio of 5:5 to obtain an electron transport layer (ETL) with a thickness of 30 nm.

[0166] Magnesium (Mg) and silver (Ag) are mixed in a mass ratio of 9:1 and vapor-deposited onto the electron transport layer (ETL) to form an electron injection layer (EIL) with a thickness of 50 nm.

[0167] Subsequently, silver (Ag) is vapor-deposited onto the electron injection layer to form a cathode with a thickness of 100 nm. A 50 nm thick DNTPD is then deposited on the cathode sealing layer. Furthermore, the cathode surface is sealed with a UV-curable adhesive and a sealing cap containing a desiccant to protect the organic electroluminescent device from the influence of atmospheric oxygen or moisture. Thus, an organic electroluminescent device is prepared.

[0168]

[0169]

[0170] Application Examples 55-65

[0171] Compounds 272, 273, 274, 285, 286, 300, 301, 302, 303, 315, and 316 of the present invention were used as GPLs, with other parts consistent with Application Example 54, thereby fabricating organic electroluminescent devices of Application Examples 55-65. Comparative Examples 1-4:

[0172] The difference from Application Example 54 is that compounds P2a, P7a, P4c, and P10c from CN115956073A are used instead of compound 271 in this application as GPL, while the rest is the same as Application Example 1.

[0173] The organic electroluminescent device manufactured in the above application example and the organic electroluminescent device manufactured in the comparative example have the characteristic of operating at a current density of 10 mA / cm². 2 The results were measured under the specified conditions and are shown in Table 8.

[0174] Table 8:

[0175]

[0176]

[0177] As shown in Table 8 above, when the compound of the present invention is used as GPL in green organic electroluminescent devices, the luminous efficiency is significantly improved at the same current density, the device start-up voltage is reduced, and the power consumption of the device is relatively reduced.

[0178] The organic electroluminescent devices prepared in Comparative Examples 1-4 and Application Examples 55-65 were subjected to luminescence lifetime tests to obtain the luminescence lifetime T97% data (the time for the luminous brightness to decrease to 97% of the initial brightness). The testing equipment was a TEO luminescent device lifetime testing system. The results are shown in Table 9:

[0179] Table 9:

[0180]

[0181] As shown in Table 9 above, when the compound of the present invention is used as a GPL in a green organic electroluminescent device, its lifespan is further improved compared with the compound in the prior art at the same current density, and it has broad application prospects.

Claims

1. An amino compound containing a benzo[phenanthrene]furan group, characterized in that, An amino compound containing a benzo[phenanthrene]furan group is one of the following compounds with the following structural formula: 。 2. An organic electroluminescent device, characterized in that, It includes a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, said organic layer containing an amine compound with a benzophenanthrene furan group as described in claim 1.

3. The organic electroluminescent device according to claim 2, characterized in that, The organic layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer; at least one of the hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, and electron injection layer contains the aforementioned amine compound with a benzo[phenanthrene]furan group.

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