An organic compound containing a polyfluorosubstituted glutarimide or succinimide class and an organic electroluminescence device comprising the same

Abstract

The application discloses a kind of containing polyfluorine-substituted glutarimide or succinimide class organic compound and the organic electroluminescent device comprising it.The compound of the present application is a kind of containing polyfluorine-substituted glutarimide or succinimide class organic compound, the compound of the present application has lower visible light refractive index in the field of visible light, and the refractive index in blue light region is lower than 1.60.The present application is a low refractive index material, which is matched with a high refractive index material to form a low-high double-layer cover layer, and when applied to an OLED device, the light extraction efficiency of the OLED device can be effectively improved, and the angle dependence can be greatly reduced, thereby improving the luminous efficiency of the device and optimizing the viewing angle performance.

Description

Technical Field

[0001] This invention relates to the field of semiconductor technology, and more particularly to an organic compound containing polyfluorinated glutarimide or succinimide and its use as a capping layer in organic electroluminescent devices. Background Technology

[0002] Organic light-emitting diodes (OLEDs), also known as organic electroluminescent devices, are a technology that uses organic materials to emit light through carrier injection and recombination under the influence of an electric field. They convert electrical energy into light energy through organic light-emitting materials, including passive-matrix OLEDs (PMOLEDs) and active-matrix OLEDs (AMOLEDs). OLEDs are a next-generation display technology following cathode ray tubes (CRTs) and liquid crystal displays (LCDs), and are hailed as a dream display technology. Essentially, an OLED is a thin-film stacked device. Theoretically, with both the anode and cathode being transparent electrodes, light emitted from the light-emitting layer can propagate from either the anode or the cathode to the outside of the device. Therefore, based on the different light propagation paths, the devices can be classified as bottom-emitting devices and top-emitting devices.

[0003] In a bottom-emitting device, light propagates from the anode through the substrate to the outside of the device, while in a top-emitting device, light propagates through the cathode to the outside of the device. The different light emission methods of these two devices lead to vastly different applications. If a bottom-emitting device is used in an active matrix structure, its light emission path is organic layer-anode-TFT-substrate. The TFT is a mesh array switch deposited on the substrate. The presence of the TFT further reduces the aperture ratio of the device, causing the emitted light to be reflected and scattered at this point, preventing it from propagating to the outside of the device and severely impacting the display effect. In contrast, the top-emitting device emits light from the cathode side, bypassing the substrate and thus avoiding the TFT structure. This successfully avoids the reduced aperture ratio problem seen in bottom-emitting devices, resulting in a more detailed and clearer image with higher color vibrancy.

[0004] In top-emitting organic electroluminescent devices, the metal cathode layer and the bottom metal reflective layer form a resonant cavity (also called a microcavity), resulting in both constructive and destructive interference. As the viewing angle changes, the distance between the metal cathode layer and the bottom metal reflective layer (i.e., the cavity length of the microcavity) changes accordingly. This leads to significant differences in brightness and color observed at different viewing angles, severely impacting product performance.

[0005] In such light-emitting elements, when light emitted from the light-emitting layer is incident on other films at an angle greater than a certain value, total internal reflection will occur at the interface between the light-emitting layer and the other films. Therefore, only a portion of the emitted light can be utilized. In recent years, to improve light extraction efficiency and reduce color shift, light-emitting elements with a high-refractive-index "coating layer" placed on the outside of a semi-transparent electrode with a low refractive index have been proposed.

[0006] However, increasing the refractive index of the organic compounds used for the capping layer is very difficult. Therefore, in order to further improve the luminous efficiency of organic light-emitting elements without adding too much material, a dual-capping layer structure consisting of a low-refractive-index capping layer and a high-refractive-index capping layer was explored. Although Samsung's US20210159427A1 patent also uses a combination of low-refractive-index and high-refractive-index materials to form a dual-capping layer, its low-refractive-index material is a coordination compound with poor coordination bond stability. This patent only describes that it can improve the luminous efficiency of the device, but does not describe the effect on the apparent polarization of the device. Although the patent WO2022075396A1 by Baotu Valley also uses a combination of low-refractive-index and high-refractive-index materials to form a double-layer coating, its low-refractive-index material uses adamantane as the core, with aryl or heteroaryl groups connected on both sides by bridging groups such as amine, amide, ester, and ether groups. The disclosed structure has a low molecular weight and a low evaporation temperature of less than 200°C. The evaporation rate is unstable during the evaporation process, which is prone to material spraying and contamination of the evaporation equipment. Moreover, the film is prone to crystallization after coating, which affects the stability of the device, especially the stability of high-temperature devices. Furthermore, the patent only describes that it can improve the luminous efficiency of the device, but does not describe the effect on the apparent polarization of the device.

[0007] Due to the refractive index difference between the high-refractive-index CPL and the low-refractive-index CPL in the double capping layer, a portion of the light emitted from the light-emitting layer passes through the capping layer, while the remaining portion is reflected by the capping layer. Light is particularly reflected at the interfaces between the high-refractive-index CPL and the low-refractive-index CPL, and at the interface between the high-refractive-index CPL and the encapsulation structure. The light reflected by the capping layer is reflected again at the electrodes and is amplified during repeated reflections. Therefore, repeated reflections can occur at the interfaces between the high-refractive-index CPL and the low-refractive-index CPL, and at the interface between the high-refractive-index CPL and the encapsulation structure, thereby recovering light lost due to reflection on the surface facing away from the OLED.

[0008] While the use of high-precision metal masks in the formation of capping layers has been proposed, the following problems exist: if the deposition temperature of the capping layer is too high, deformation caused by heat will lead to poor alignment accuracy. Furthermore, with high-precision masks, deposition cannot be performed at the correct positions. Many inorganic materials require high deposition temperatures, making them unsuitable for the use of high-precision masks and potentially damaging the light-emitting element itself. Moreover, for film deposition using sputtering methods, capping layers made of inorganic materials cannot be used due to the potential damage to the light-emitting element.

[0009] For devices exposed to high-energy plasma or ultraviolet light during subsequent packaging, a stable material is needed to prevent damage to the internal materials of the electroluminescent device. LiF is currently widely used. The protective layer of LiF has high chemical reactivity, while the TFE encapsulation layer is generally prepared using CVD technology. This process generates a large amount of high-energy plasma, releasing significant energy and electrons into the internal structure of the device. The energy released by the high-energy plasma can cause the organic material in the capping layer to interact with the adjacent LiF layer, leading to black spots on the device. Additionally, the layer closest to the protective layer in the encapsulation layer may also participate in the interaction, contributing to the black spot phenomenon.

[0010] The current method of using capping layers to improve the performance of OLED devices mainly has the following problems:

[0011] 1. If the vapor deposition temperature is too high, the CPL material will decompose severely after prolonged vapor deposition.

[0012] 2. Under controlled low vapor deposition temperatures, the refractive index of organic CPL materials cannot be increased indefinitely.

[0013] 3. The light extraction efficiency is low, and when applied to OLED devices, the improvement in device luminous efficiency is limited.

[0014] 4. When applied to OLED devices, the color deviation of the device is not significantly improved, and the angle of the emitted light is highly dependent. As the angle changes, the brightness decreases, accompanied by changes in the emitted color.

[0015] To continuously improve the performance of OLED devices, innovation in OLED device structure and manufacturing processes is needed, as well as ongoing research and innovation in OLED optoelectronic functional materials to create higher-performance OLED functional materials. Therefore, finding suitable low-refractive-index materials paired with high-refractive-index materials as a double-layer capping layer for OLED devices to address the aforementioned issues is a long-standing need in this field. Summary of the Invention

[0016] To address the aforementioned problems in the prior art, this application provides an organic compound containing polyfluorinated substituted glutarimide or succinimidide. The compound of this invention exhibits a low refractive index in the blue light region. This low-refractive-index compound can be used as a first capping layer in conjunction with a high-refractive-index second capping layer to improve light extraction efficiency and reduce angle dependence.

[0017] An organic compound containing a polyfluorinated glutarimide or succinimide, said organic compound having a structure as shown in general formula (1):

[0018]

[0019] In general formula (1), each occurrence of Z, whether identical or different, independently represents CR or N; Z at connections with other groups is represented as C;

[0020] In general formula (1), L represents a single bond, a substituted or unsubstituted C6-C50 arylene, or a C2-C50 heteroarylene containing one or more heteroatoms substituted or unsubstituted; f represents the number 0 or 1; e represents the number 1 or 2;

[0021] In general formula (1), L1, L2, and L3 each independently represent a single bond, a substituted or unsubstituted C6-C50 arylene, or a C2-C50 heteroarylene containing one or more heteroatoms substituted or unsubstituted.

[0022] In general formula (1), a represents the number 1, 2, 3, 4, 5 or 6; b and c represent the number 0, 1, 2, 3, 4 or 5;

[0023] When e represents the number 1, a + b + c ≥ 3; when e represents the number 2, a + b + c ≥ 1.

[0024] In general formula (1), Ar1 represents general formula (2); Ar2 and Ar3 each independently represent substituted or unsubstituted C6-C50 aryl, C2-C50 heteroaryl containing one or more heteroatoms substituted or unsubstituted, or the structure shown in general formula (2) or general formula (3);

[0025]

[0026] In general formula (2), X represents a single bond, -C(R) 10 (R) 11 )-

[0027] In general formula (2), each of R1 to R4, whether the same or different, independently represents a hydrogen atom, a fluorine atom, or a trifluoromethyl atom; R1 to R4 cannot simultaneously represent a hydrogen atom.

[0028] The R, R5 to R 11 Each instance of the same or different independently represents cyano, halogen, hydrogen atom, deuterium, tritium, fluorine atom, trifluoromethyl, trifluoromethoxy, difluoromethyl, difluoromethoxy, fluoromethyl, fluoromethoxy, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, or tert-butoxy; R5 to R9 can also be represented as general formula (2), substituted or unsubstituted C6-30 aryl, or C2-30 heteroaryl containing one or more heteroatoms substituted or unsubstituted;

[0029] The substituents of the "substituted or unsubstituted" group are selected from one or more of the following: protium atom, deuterium atom, tritium atom, halogen atom, cyanotrifluoromethyl, trifluoromethoxy, difluoromethyl, difluoromethoxy, fluoromethyl, fluoromethoxy, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, C6-C20 aryl, and C2-C20 heteroaryl containing one or more heteroatoms;

[0030] The heteroatoms in the C2-C50 heteroaryl, C2-C50 heteroaryl, C2-C30 heteroaryl, and C2-C20 heteroaryl are selected from nitrogen, oxygen, phosphorus, sulfur, or fluorine.

[0031] Preferably, the structures of the polyfluorinated glutarimide or succinimide organic compounds are as shown in general formulas (4) to (9):

[0032]

[0033] The Z, L, L1, L2, L3, X, R1 to R 11 The definition is the same as that in claim 1;

[0034] In general formulas (4) to (6), a+b+c≥3;

[0035] In general formulas (7) to (9), a+b+c≥1.

[0036] Furthermore, it is preferred that each of R1 to R4, whether identical or different, independently represents a hydrogen atom, a fluorine atom, or a trifluoromethyl group; and R1 to R4 cannot simultaneously be hydrogen atoms.

[0037] X represents a single bond, -C(H)2-, -C(H)(F)-, -C(F)(CF3)-, -C(F)2-, -C(F)(CF3)-, -C(CF3)2-;

[0038] Each of the R5 to R9, whether identical or different, independently represents a cyano group, halogen, hydrogen atom, deuterium, tritium, fluorine atom, trifluoromethyl, trifluoromethoxy, difluoromethyl, difluoromethoxy, fluoromethyl, fluoromethoxy, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy. Substituted or unsubstituted phenyl, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted pyridylene, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted phenanthrene, substituted or unsubstituted benzophenanthrene, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted triazine, substituted or unsubstituted furanyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted benzooxazolyl, substituted or unsubstituted bisbenzooxazolyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl,

[0039] Each occurrence of Z, whether identical or different, independently represents CR or N;

[0040] Each instance of R, whether identical or different, independently represents a cyano group, halogen, hydrogen atom, deuterium, tritium, fluorine atom, trifluoromethyl, trifluoromethoxy, difluoromethyl, difluoromethoxy, fluoromethyl, fluoromethoxy, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, or tert-butoxy.

[0041] L, L1, L2, and L3 each independently represent a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted diphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted pyridylene, or a substituted or unsubstituted pyrimidinylene.

[0042] The substituents in the "substituted or unsubstituted" designation are selected from protium, deuterium, tritium, halogen, cyano, trifluoromethyl, trifluoromethoxy, difluoromethyl, difluoromethoxy, fluoromethyl, fluoromethoxy, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, phenyl, diphenyl, terphenyl, naphthyl, phenanthrene, benzo[a]phenanthrene, pyridyl, pyrimidinyl, oxadiazolyl, triazinyl, furanyl, dibenzofuranyl, dibenzothiopheneyl, benzo[a]oxazolyl, substituted or unsubstituted bisbenzo[a]oxazolyl, carbazole, N-phenylcarbazole, quinolinyl, isoquinolinyl, etc.

[0043] Further preferably, R1 to R4 represent fluorine atoms; X represents a single bond or -C(F)2-;

[0044] At least one of R5 to R9 is represented as trifluoromethyl, and preferably at least two are represented as trifluoromethyl.

[0045] Preferably, the structures of the polyfluorinated glutarimide or succinimide organic compounds are as shown in general formula (1-1) or general formula (1-2):

[0046]

[0047] In general formulas (1-1) and (1-2), each occurrence of Z, whether identical or different, independently represents CR or N; Z at connections with other groups is represented as C;

[0048] L1, L2, and L3 each independently represent a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted diphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted pyridylene, or a substituted or unsubstituted pyrimidinylene.

[0049] Ar1 represents the structure shown in general formula (2); Ar2 and Ar3 are each independent structures shown in general formula (2) or general formula (3);

[0050]

[0051] In general formula (2), X represents a single bond, -C(R) 10 (R) 11 )-

[0052] In general formula (2), each of R1 to R4, whether the same or different, independently represents a hydrogen atom, a fluorine atom, or a trifluoromethyl atom; R1 to R4 cannot simultaneously represent a hydrogen atom.

[0053] The R, R5 to R 11 Each occurrence, whether identical or different, independently represents a cyano group, halogen, hydrogen atom, deuterium, tritium, fluorine atom, trifluoromethyl, trifluoromethoxy, difluoromethyl, difluoromethoxy, fluoromethyl, fluoromethoxy, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, or tert-butoxy.

[0054] The substituents in the "substituted or unsubstituted" designation are selected from protium, deuterium, tritium, halogen, cyano, trifluoromethyl, trifluoromethoxy, difluoromethyl, difluoromethoxy, fluoromethyl, fluoromethoxy, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, phenyl, diphenyl, terphenyl, naphthyl, phenanthrene, benzo[a]phenanthrene, pyridyl, pyrimidinyl, oxadiazolyl, triazinyl, furanyl, dibenzofuranyl, dibenzothiopheneyl, benzo[a]oxazolyl, substituted or unsubstituted bisbenzo[a]oxazolyl, carbazole, N-phenylcarbazole, quinolinyl, isoquinolinyl, etc.

[0055] Preferably, the structures of the polyfluorinated glutarimide or succinimide organic compounds are as shown in general formulas (1-3) to (1-6):

[0056]

[0057] In general formulas (1-3) to (1-6), Z, L1, L2, L3, Ar1, Ar2, and Ar3 are defined in the same way as in general formula (1-2).

[0058] Preferably, Ar1 is represented as:

[0059]

[0060] Ar2 and Ar3 can be represented by any of the following structures:

[0061]

[0062]

[0063] L1, L2, and L3 are represented as follows:

[0064] single bond,

[0065] The organic compound is further preferably constructed using any of the following structural formulas:

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076] Preferably, the refractive index of the organic compound under blue light at a wavelength of 460 nm is in the range of 1.4-1.7, and more preferably 1.4-1.6.

[0077] The organic electroluminescent device of the present invention includes:

[0078] Substrate layer;

[0079] A first electrode, which is on the substrate layer;

[0080] An organic light-emitting functional layer is disposed on the first electrode;

[0081] A second electrode, which is situated on the organic light-emitting functional layer; and

[0082] A capping layer is applied over the second electrode;

[0083] The coating layer comprises one or more of the above-described organic compounds containing polyfluorinated substituted glutarimide or succinimide.

[0084] Preferably, in the organic electroluminescent device, the capping layer includes a first capping layer and a second capping layer.

[0085] The first covering layer is on top of the second electrode;

[0086] The second cover layer is on top of the first cover layer;

[0087] The first capping layer comprises one or more of the above-described polyfluorinated glutarimide or succinimide organic compounds.

[0088] Preferably, the refractive index of the first cover layer material is less than that of the second cover layer material, the refractive index of the first cover layer material at a wavelength of 460 nm is less than or equal to 1.60, the refractive index of the second cover layer material at a wavelength of 460 nm is greater than or equal to 1.85, and the difference between the refractive indices of the second cover layer material and the first cover layer material at a wavelength of 460 nm is greater than or equal to 0.3.

[0089] Further preferably, the band gap Eg of the first capping layer material is greater than 3.0 eV, more preferably greater than 3.5 eV, and the difference in refractive index of the first capping layer material at wavelengths of 460 nm and 620 nm is less than or equal to 0.3.

[0090] The total thickness of the capping layer is 15-300nm, more preferably 30-200nm, even more preferably 40nm-100nm, and most preferably 50-80nm; the thickness of the first capping layer is 1-150nm, preferably 5-100nm, and even more preferably 10-50nm; the thickness of the second capping layer is 1-150nm, preferably 10-100nm, and even more preferably 20-80nm.

[0091] In this document, the term "aryl" refers to a monocyclic, bicyclic, or polycyclic aromatic system having a specified number of ring carbon atoms (preferably 6 to 50, particularly 6 to 30) with optional substitution in each case, such as "C6-C50 aryl," examples of which include, but are not limited to, phenyl, benzyl, biphenyl, naphthyl, anthracene, phenanthrene, 9,10-benzophenanthrene, condensed tetraphenyl, pyrene, diphenyl, para-triphenyl, meta-triphenyl, etc. Aryl, triphenylene, perylene, indene, triphenylene, fumoniyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, etc. "Arylene" refers to a divalent group in a monocyclic, bicyclic, or polycyclic aromatic system having a specified number of ring carbon atoms (preferably 6 to 50, particularly 6 to 30), optionally substituted in each case, examples of which include, but are not limited to, divalent groups of the aforementioned groups.

[0092] In this document, the term "heteroaryl" refers to an aromatic group having, in each case, a specified number of ring carbon atoms (preferably 2 to 50, particularly 2 to 30) and at least one heteroatom selected from N, O, S, and P. For example, "C2-C50 heteroaryl" includes, but is not limited to, furanyl, thiopheneyl, pyrroleyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, and 1,2,4-thiadiazolyl. 1,3,4-Thiadiazolyl, 1,2,5-Thiadiazolyl, Tetrazolyl, Pyridyl, Pyrimidinyl, Pyridazinyl, 1,2,3-Triazinyl, 1,2,4-Triazinyl, 1,3,5-Triazinyl, Benzofuranyl, Benzoisofuranyl, Benzothiophenyl, Benzoisothiophenyl, Indoleyl, Isoyndoleyl, Inzazoleyl, Benzimidazolyl, Benzooxazolyl, Benzoisooxazolyl Benzothiazolyl, 2,1,3-benzoxadiazole, quinolinyl, isoquinolinyl, terolinyl, phthalazinyl, quinazolinyl, quinolinyl, naphthidyl, benzotriazinyl, benzoxazinyl, purine, pteridinyl, indazinyl, benzothiazinyl, acridineyl, benaziryl, benazirylthiazinyl, benaziryl, dibenzofuranyl, dibenzothiophenyl, carbazoleyl, naphthiazinyl, quinolinyl, isoquinolinyl, indole [1,2-f]phenanthridine, imidazo[2,1-a]isoquinolinyl, imidazo[1,2-a]quinolinyl, benzo[4,5]imidazo[1,2-a]pyridyl, imidazo[1,2-a]pyridyl, benzofuran[3,2-c]quinolinyl, naphtho[1,2-b]benzofuranyl, naphtho[2,3-b]benzofuranyl, etc., are aromatic composite groups having heteroatoms. "Hypoaryrhearyl" refers to a divalent group having a specified number of ring carbon atoms (preferably 2 to 50, particularly 2 to 30) and at least one heteroatom selected from N, O, S, and P, examples of which include, but are not limited to, divalent groups of the above-mentioned groups.

[0093] Technical effects of the invention:

[0094] The compound of this invention has a refractive index below 1.60 in the blue light region. The fluorinated compound of this invention is a low-refractive-index organic material, with a stable vapor deposition process. During film formation, it does not form material clusters, thus improving the yield rate of display screen manufacturing. The low-refractive-index compound of this invention can be used as a first capping layer in combination with a high-refractive-index second capping layer to improve light extraction efficiency and reduce angle dependence. Attached Figure Description

[0095] Figure 1 A cross-sectional structural schematic diagram of an application example of the compound of the present invention (top-emitting organic electroluminescent device).

[0096] In this design, 100 is the substrate, 200 is the first electrode, 300 is the organic light-emitting functional layer, 400 is the second electrode, and 500 is the capping layer.

[0097] Figure 2 for Figure 1 Schematic diagram of the cross-sectional structure of the organic light-emitting functional layer 300 of the top-emitting organic electroluminescent device.

[0098] Among them, 310 (HIL) is the hole injection layer, 320 (HTL) is the hole transport layer, 330 (EBL) is the electron blocking layer, 340 (EML) is the light emitting layer, 350 (HBL) is the hole blocking layer, 360 (ETL) is the electron transport layer, and 370 (EIL) is the electron injection layer.

[0099] Figure 3 for Figure 1 Schematic diagram of the cross-sectional structure of the middle overburden layer

[0100] Among them, 510 is the first capping layer with low refractive index, and 520 is the second capping layer with high refractive index. Detailed Implementation

[0101] Throughout this specification, unless explicitly stated otherwise, the term "including" any component will be understood to imply the inclusion of other components, not to exclude any other components. Furthermore, it should be understood that throughout this specification, when an element such as a layer, film, region, or substrate is referred to as being "on" or "above" another element, it may be "directly on" the other element, or there may be intermediate elements present. Additionally, "on" or "above" means located above the target portion, and not necessarily above it in the direction of gravity.

[0102] In this paper, "n@460nm" refers to the refractive index of the material relative to vacuum for blue light at a wavelength of 460nm; "n@525nm" refers to the refractive index of the material relative to vacuum for green light at a wavelength of 525nm; "n@620nm" refers to the refractive index of the material relative to vacuum for red light at a wavelength of 620nm; and "k@380nm" refers to the extinction coefficient of the material relative to vacuum for a wavelength of 380nm.

[0103] In this document, C6-C50 aryl refers to a monovalent group comprising a carbocyclic aromatic system having 6 to 50 carbon atoms as cyclic atoms. Non-limiting examples of C6-C50 aryl groups may include phenyl, biphenyl, phenanthryl, triphenyl, naphthyl, phenanthryl, benzo[a]phenanthryl, benzyl, anthracene, 9,10-benzo[a]phenanthryl, tetraphenyl, pyrene, diphenyl, p-triphenyl, meta-triphenyl, etc. Aryl, triphenylene, peryl, indene, triphenylene, fenenyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzodimethylfluorenyl, etc. When the C6-C50 aryl group includes two or more rings, these rings can fused together.

[0104] In this document, non-limiting examples of C2-C50 heteroaryl groups may include furanyl, thiopheneyl, pyrroleyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl. 1,3,4-Thiadiazolyl, 1,2,5-Thiadiazolyl, Tetrazolyl, Pyridyl, Pyrimidinyl, Pyridazinyl, 1,2,3-Triazinyl, 1,2,4-Triazinyl, 1,3,5-Triazinyl, Benzofuranyl, Benzoisofuranyl, Benzothiophenyl, Benzoisothiophenyl, Indoleyl, Isoyndoleyl, Inzazoleyl, Benzimidazolyl, Benzooxazolyl, Benzoisooxazolyl, Benzothiophenyl Azolyl, 2,1,3-benzoxadiazole, quinolinyl, isoquinolinyl, terolinyl, phthalazinyl, quinazolinyl, quinolinyl, naphthidyl, benzotriazinyl, benzoxazinyl, purineyl, pteridinyl, indazinyl, benzothiazinyl, acridineyl, benaziryl, benaziryl, benaziryloxazinyl, dibenzofuranyl, dibenzothiophenyl, carbazoleyl, naphthiazinyl, quinolinyl, isoquinolinyl, indole[1,2] -f] phenanthridine, imidazo[2,1-a]isoquinolinyl, imidazo[1,2-a]quinolinyl, benzo[4,5]imidazo[1,2-a]pyridyl, imidazo[1,2-a]pyridyl, benzofuran[3,2-c]quinolinyl, naphtho[1,2-b]benzofuranyl, naphtho[2,3-b]benzofuranyl, etc., also including aromatic composite groups with heteroatoms, etc. When C2-C 50When a heteroaryl group comprises two or more rings, these rings can fused together.

[0105] In this article, C6-C is used 20 An aryl group is a monovalent group in a carbocyclic aromatic system comprising 6 to 20 carbon atoms as cyclic atoms. (C6-C) 20 Non-limiting examples of aryl groups may include phenyl, biphenyl, phenanthryl, triphenyl, naphthyl, phenanthryl, benzo[a]phenanthryl, benzyl, anthracene, 9,10-benzo[a]phenanthryl, fused tetraphenyl, pyrene, diphenyl, p-triphenyl, meta-triphenyl, etc. It includes compounds such as methyl, triphenyl, peryl, indene, triphenyl, fumoni, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzodimethylfluorenyl, etc.

[0106] The C2-C used in this article 20 A heteroaryl group is a monovalent group comprising a carbocyclic aromatic system having at least one heteroatom selected from N, O, P, and S as the cyclic atom and 2 to 20 carbon atoms. (C2-C) 20 Non-limiting examples of heteroaryl groups may include pyridyl, oxadiazolyl, triazinyl, pyrimidinyl, furanyl, dibenzofuranyl, dibenzothiophenyl, benzooxazolyl, bisbenzooxazolyl, carbazoyl, N-phenylcarbazoyl, quinolinyl, isoquinolinyl, naphthofuranyl, and phenyl-substituted naphthofuranyl.

[0107] In this article, C6-C 50 Aryl groups refer to phenylene, naphthylene, anthraceneylene, fluoreneylene, dimethylfluoreneylene, diphenylfluoreneylene, spirofluoreneylene, phenanthreneylene, tetraphenylene, pyreneylene, biphenylene, para-triphenylene, meta-triphenylene, and so on. It can be alkyl, triphenylene, perylene, indene, but is not limited to these.

[0108] In this article, C2-C 50 The term "heteroaryl" refers to fused rings of the following groups: furanyl, thiopheneyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiazolyl, pyridinyl, pyrimidinyl, pyrazinyl, triazinyl, benzofuranyl, benzothiopheneyl, benzoimidazolyl, indolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinolinyl, naphridinyl, benzooxazinyl, benzothiazinyl, acridineyl, phenazinyl, phenthiazinyl, phenoxazinyl, fenenyl, dibenzofuranyl, dibenzothiopheneyl, carbazolyl, or combinations thereof, but is not limited to these.

[0109] Organic electroluminescent devices

[0110] The compounds of this invention are particularly suitable for use in vapor deposition and for improving light extraction efficiency, thereby enhancing the stability of the manufacturing process, expanding the optimal vapor deposition film thickness range, and preventing black spot phenomena in devices. The resulting devices or components exhibit high yield and high visible light extraction efficiency. Therefore, one object of this invention is to provide an electroluminescent device comprising:

[0111] Substrate layer;

[0112] A first electrode, which is on the substrate layer;

[0113] An organic light-emitting functional layer is disposed on the first electrode;

[0114] A second electrode, which is situated on the organic light-emitting functional layer; and

[0115] A capping layer is applied over the second electrode;

[0116] The coating layer comprises one or more of the above-described organic compounds containing polyfluorinated substituted glutarimide or succinimide.

[0117] In one embodiment of the present invention, the refractive index of the first capping layer is less than the refractive index of the second capping layer; the refractive index of the first capping layer at 460 nm is less than or equal to 1.65, preferably less than or equal to 1.60, preferably less than or equal to 1.55; preferably less than or equal to 1.50; the refractive index of the first capping layer at 525 nm is less than or equal to 1.65, preferably less than or equal to 1.60, preferably less than or equal to 1.55; preferably less than or equal to 1.50; the refractive index of the first capping layer at 620 nm is less than or equal to 1.65, preferably less than or equal to 1.60, preferably less than or equal to 1.55; preferably less than... The refractive index of the second capping layer at 460nm is greater than or equal to 1.85, preferably greater than or equal to 1.9, preferably greater than or equal to 2.0, preferably greater than or equal to 2.1, preferably greater than or equal to 2.2; more preferably greater than or equal to 2.3; the refractive index of the second capping layer at 525nm is greater than or equal to 1.85, preferably greater than or equal to 1.9, preferably greater than or equal to 2.0, preferably greater than or equal to 2.1, more preferably greater than or equal to 2.2; the refractive index of the second capping layer at 620nm is greater than or equal to 1.8, preferably greater than or equal to 1.9, preferably greater than or equal to 2.0, more preferably greater than or equal to 2.1.

[0118] In one embodiment of the present invention, the difference in refractive index @460nm between the first capping layer and the second capping layer is greater than or equal to 0.3; preferably greater than or equal to 0.4; preferably greater than or equal to 0.5; preferably greater than or equal to 0.6; preferably greater than or equal to 0.7; more preferably greater than or equal to 0.8.

[0119] In a preferred embodiment of the present invention, an OLED is provided, comprising a substrate, an anode, a cathode, an organic light-emitting functional layer, and a capping layer. The organic light-emitting functional layer may include a light-emitting layer, a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport layer, an electron injection layer, etc., or may only include a light-emitting layer and one or more other layers. The capping layer is composed of one or more compounds of the above-described general formula (1) or includes one or more compounds of general formula (1). Optionally, a protective layer and an encapsulation layer are further provided above the capping layer.

[0120] like Figure 1 As shown, substrate 100 can be any substrate typically used in organic light-emitting devices. It can be a glass or transparent plastic substrate, an opaque material such as silicon or stainless steel, or a flexible PI film. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and water resistance, and their applications vary depending on their properties.

[0121] A first electrode 200 is formed on the substrate 100. The first electrode 200 can be either a cathode or an anode. Here, the first electrode 200 can be simply a reflective electrode, such as a reflective film formed of silver (Ag), magnesium (Mg), aluminum (Al), gold (Au), nickel (Ni), chromium (Cr) or their alloys, or it can be an electrode composed of a reflective film and a transparent or semi-transparent electrode, for example, a transparent or semi-transparent electrode layer with high work function formed on the reflective film. The transparent or semi-transparent electrode layer can be formed of indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), aluminum zinc oxide (AZO), indium gallium oxide (IGO), indium oxide (In2O3), or tin oxide (SnO2); it can also be composed of a combination of metal and oxide, such as ITO / Ag / ITO, IGO / Al / IGO, or AZO / Ag / AZO.

[0122] The first electrode 200 can be formed by methods such as sputtering, ion plating, vacuum evaporation, spin coating, electron beam evaporation or chemical vapor deposition (CVD), preferably by sputtering.

[0123] The thickness of the first electrode layer 200 depends on the material used, and is typically 5nm-1μm, preferably 10nm-1μm, more preferably 10nm-500nm, particularly preferably 10nm-300nm, and most preferably 10nm-200nm.

[0124] like Figure 2As shown, the organic light-emitting functional layer 300 may include a light-emitting layer 340 (EML), and if the first electrode 200 is an anode, a hole transport region may be formed between the EML and the first electrode 200, and an electron transport region may be formed between the EML and the second electrode layer 400; if the first electrode 200 is a cathode, an electron transport region may be formed between the EML and the first electrode 200, and a hole transport region may be formed between the EML and the second electrode layer 400. The hole transport region may include at least one of a hole injection layer 310 (HIL), a hole transport layer 320 (HTL), and an electron blocking layer 330 (EBL). The electron transport region may include at least one of a hole blocking layer 350 (HBL), an electron transport layer 360 (ETL), and an electron injection layer 370 (EIL). Therefore, the organic light-emitting functional layer 300 includes a light-emitting layer and a combination of at least two of the following layers: a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0125] The thickness of the organic light-emitting functional layer 300 is 50nm-1000nm.

[0126] As for the materials used in the hole injection layer, hole transport layer, and electron blocking layer (HIL310, HTL320, EBL330), any material can be selected from known materials used in OLED devices.

[0127] At least one layer of HIL310 and HTL320 may further include a charge-generating material for improving conductivity. The charge-generating material may be a p-dopant. Non-limiting compounds of p-dopants include: quinone derivatives, such as tetracyanoquinone dimethyl (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethyl (F4-TCNQ); or hexaazatriphenyl derivatives, such as 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenyl (HAT-CN); or cyclopropane derivatives, such as 4,4′,4″-((1E,1′E,1″E)-cyclopropane-1,2,3-trimethylenetris(cyanoformyl))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides, such as tungsten oxide and molybdenum oxide, but not limited thereto.

[0128] In EBL330, the triplet (T1) energy level of the material is required to be higher than the T1 energy level of the host material in the emissive layer 340, which can effectively block energy loss from the emissive layer material. The HOMO energy level of the EBL330 material is between the HOMO energy level of the HTL320 material and the HOMO energy level of the host material in the emissive layer 340, which facilitates hole injection from the positive electrode into the emissive layer. At the same time, the EBL330 material is required to have high hole mobility, which is beneficial for hole transport and reduces the power consumption of the device. The LUMO energy level of the EBL330 material is higher than the LUMO energy level of the host material in the emissive layer 340, which acts as an electron blocker, that is, the EBL330 material is required to have a wide bandgap (Eg). EBL330 materials that meet the above conditions can be triarylamine derivatives, fluorene derivatives, spirofluorene derivatives, dibenzofuran derivatives, carbazole derivatives, etc. Preferred are triarylamine derivatives, such as N4,N4-bis([1,1′-biphenyl]-4-yl)-N4′-phenylN4′-[1,1′:4′,1″-terphenyl]-4-yl-[1,1′-biphenyl]-4,4′-diamine; spirofluorene derivatives, such as N-([1,1′-diphenyl]-4-yl)N-(9,9-dimethyl-9H-furan-2-yl)-9,9′-spirodifluorene-2-amine; dibenzofuran derivatives, such as N,N-bis([1,1′-biphenyl]-4-yl)-3′-(dibenzo[b,d]furan-4-yl)-[1,1′-biphenyl]-4-amine, but not limited thereto.

[0129] To obtain a high-efficiency OLED device, its light-emitting layer 340 can use the same doping material or multiple doping materials. The doping materials can be simple fluorescent materials, delayed fluorescence (TADF) materials, or phosphorescent materials, or a combination of different fluorescent materials, TADF materials, and phosphorescent materials. The light-emitting layer 340 can be a single light-emitting layer material or a composite light-emitting layer material stacked laterally or vertically. The light-emitting layer 340 constituting the above-mentioned OLED light emitter can be selected from the following various structures:

[0130] (1) Single organic light-emitting layer material;

[0131] (2) Any combination of blue organic light-emitting layer material and green, yellow or red light-emitting layer material, in no particular order;

[0132] (3) Any two combinations of blue organic light-emitting layer material and green, yellow or red light-emitting layer material, without regard to the order of their arrangement;

[0133] (4) Blue organic light-emitting layer material, green organic light-emitting layer material, and red organic light-emitting layer material are arranged horizontally.

[0134] In order to regulate the effective binding of charge carriers in the light-emitting layer, the film thickness of the light-emitting layer 340 constituting the OLED light emitter can be adjusted arbitrarily as needed, or light-emitting layers of different colors can be alternately stacked and combined as needed, and charge blocking layers with different functions can be added to the organic layers adjacent to the light-emitting layer.

[0135] The host material of the light-emitting layer constituting the aforementioned OLED light emitter not only needs to possess bipolar charge transport characteristics, but also needs to have an appropriate energy level to effectively transfer the excitation energy generated by electron-hole recombination to the guest light-emitting material, i.e., the doped material. Examples of such materials include stilbene arylene derivatives, stilbene derivatives, carbazole derivatives, triarylamine derivatives, anthracene derivatives, pyrene derivatives, triazine derivatives, xanthone derivatives, triphenylene derivatives, triazine derivatives, hexabenzobenzene derivatives, or bis(2-methyl-8-quinoline)(p-phenylphenol)aluminum (BAlq).

[0136] The materials used to form the hole blocking layer 350 and the electron transport layer 360 of the OLED device can be any material selected from those used in OLEDs that have electron transport properties. Examples of such materials include 1,3-bis[5'-(p-tert-butylphenyl)-1,3,4-oxadiazole-2'-yl]benzene, 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole and other oxadiazole derivatives, 3-(4'-tert-butylphenyl)-4-phenyl-5-(4”-biphenyl)-1,2,4-triazole and other triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, dibenzoquinone derivatives, nitro-substituted linone derivatives, thiamium dioxide derivatives, anthraquinone dimethane derivatives, thiamium dioxide derivatives, naphthylperylene and other heterocyclic tetrahydric anhydrides, carbodiimide, fluorene derivatives, anthraquinone dimethane derivatives, anthrone derivatives, stilbene pyrazine derivatives, silyrocyclopentadiene derivatives, diazonium phenanthrene derivatives, or imidazopyridine derivatives, etc.

[0137] A second electrode 400 is formed on the organic light-emitting functional layer 300. The second electrode layer can be a cathode or an anode, and can be a transparent electrode or a semi-transparent electrode. The second electrode 400 can be made of lithium, calcium, lithium fluoride / calcium, lithium fluoride / aluminum, aluminum, silver, magnesium, or alloys thereof to form a thin film with low work function. Further, the second electrode layer 400 can be made of an alloy including silver and at least one metal, said at least one metal including aluminum, platinum, ytterbium, chromium, or magnesium. Furthermore, the weight ratio of Ag in the alloy can be the same as, greater than, or less than the weight ratio of the other metals. For example, the second electrode layer 400 can be formed of an Ag-Mg alloy, wherein the mass ratio of Ag to Mg can be 90:10 to 10:90. Alternatively, the second electrode layer 400 can be formed of an alloy including at least one metal such as silver, gold, platinum, copper, nickel, or tungsten and at least one metal such as ytterbium, indium, magnesium, or chromium. These metal films can be made into transparent or semi-transparent electrodes by adjusting the film thickness. Therefore, the light generated by the organic light-emitting functional layer 300 can be emitted through the second electrode layer 400. Furthermore, the thickness of the second electrode layer 400 can be 5-20 nm.

[0138] A cover layer 500 is formed on the second electrode layer 400, the cover layer including a first cover layer 510 and a second cover layer 520.

[0139] The material used in the first covering layer is one or more of the compounds of the above general formula (1) that constitute the compound of general formula (1).

[0140] The second cover layer material can be exemplified by the following structure:

[0141]

[0142]

[0143] The total film thickness of the cover layer of the present invention is 15-300nm, preferably 30-200nm, more preferably 40nm-100nm, and most preferably 50-80nm; the film thickness of the first cover layer is 1-150nm, preferably 5-100nm, and more preferably 10-50nm; the film thickness of the second cover layer is 1-150nm, preferably 10-100nm, and more preferably 20-80nm; the film thickness of the second cover layer and the film thickness of the first cover layer may be the same or different.

[0144] refer to Figure 1 The organic electroluminescent device of the present invention includes a substrate layer 100, a first electrode layer 200, an organic light-emitting functional layer 300, a second electrode layer 400, and a capping layer 500.

[0145] A barrier layer (which may be composed of inorganic and / or organic materials and is used to prevent foreign matter from penetrating the substrate and device) and a wiring layer (which may include driving TFTs, capacitors, wires and low-temperature polysilicon LTPS) can be formed on the substrate layer using known methods.

[0146] In one specific embodiment, the first electrode 200 can be a reflective electrode and the second electrode 400 is a transparent or translucent electrode. Therefore, light generated by the organic light-emitting functional layer 300 can be directly emitted from the second electrode 400, or it can be reflected by the first electrode 200 towards the second electrode 400 before being emitted. The first electrode 200 can be prepared, for example, by vapor deposition or sputtering. The second electrode 400 can be prepared, for example, by vacuum vapor deposition.

[0147] The organic light-emitting functional layer 300 may include a light-emitting layer 340 (EML), and a hole transport region may be formed between the EML and the first electrode 200, and an electron transport region may be formed between the EML and the second electrode layer 400. The hole transport region may include at least one of a hole injection layer 310 (HIL), a hole transport layer 320 (HTL), and an electron blocking layer 330 (EBL). The electron transport region may include at least one of a hole blocking layer 350 (HBL), an electron transport layer 360 (ETL), and an electron injection layer 370 (EIL).

[0148] The organic light-emitting functional layer 300 can be composed of small-molecule organic materials or polymer materials, and the organic light-emitting functional layer 300 can be prepared by a variety of methods, such as vacuum evaporation, solution spin coating, screen printing, and inkjet printing.

[0149] The capping layer 500 may be composed of the organic compound based on the heteroarylamine structure, and the capping layer 500 may be prepared by a variety of methods, such as vacuum evaporation, solution spin coating, screen printing, and inkjet printing.

[0150] A protective layer is provided on the capping layer 500. The protective layer contains lithium fluoride (LiF). The thickness of the protective layer depends on the material used, typically 20-400 nm, preferably 30-200 nm, and more preferably 40-100 nm.

[0151] An encapsulation layer is disposed on the protective layer. The encapsulation layer is a protective structure that prevents external substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device. It is a multilayer thin film covering the entire surface of the organic layer, the capping layer, and the protective layer. It includes a first encapsulation layer on the protective layer, a second encapsulation layer on the first encapsulation layer, and a third encapsulation layer on the second encapsulation layer; the first encapsulation layer is an inorganic layer; the second encapsulation layer is an organic layer; and the third encapsulation layer is an inorganic layer containing materials selected from Al₂O₃ and SiO₂. x N y TiO2, SiO x and SiN x At least one of the groups, wherein x and y are the same or different, and x and y are independently greater than 0 and less than 10, preferably greater than 0 and less than 5, and most preferably greater than 0 and less than 3. The inorganic layer is prepared by chemical vapor deposition (CVD).

[0152] As the encapsulation layer organic material for the organic light-emitting device of the present invention, organic encapsulation layer organic materials known in the prior art for organic light-emitting devices can be used. In a preferred embodiment of the present invention, the encapsulation layer organic material used is polydimethylsiloxane (PDMS), polymethyl methacrylate (PMMA), polystyrene (PS), polymer derivatives having phenol groups, acrylic-based polymers, imide-based polymers, arylether-based polymers, amide-based polymers, fluorine-based polymers, p-xylene-based polymers, vinyl alcohol-based polymers, or mixtures thereof.

[0153] The organic material of the encapsulation layer is thick enough to cover the inorganic encapsulation layer, and the organic material of the encapsulation layer is cured into a polymer by UV curing.

[0154] According to the present invention, the organic electroluminescent device is preferably a top-emitting organic electroluminescent device, which includes, after preparing the anode, cathode and organic light-emitting functional layer, depositing a material containing the compound of general formula (1) of the present invention as a cover layer on the light-emitting side to improve light extraction efficiency and visual deviation problem.

[0155] The viewing bias problem mentioned in this article refers to the gradual change in the emitted color of a device when viewed from different angles. In this paper, improving viewing bias and reducing angle dependence is reflected in a significant decrease in the trend of color change with changing viewing angles; ideally, the emitted color does not change. This can be measured by the parameter JNCD (Just Noticeable Color Difference), which is the most noticeable color difference perceptible to the human eye. The smaller the JNCD value, the more significant the improvement in viewing bias.

[0156] Furthermore, the OLED device of the present invention can be used in OLED lighting and display devices.

[0157] Preferably, the OLED devices prepared by the present invention are used in fields such as smartphones, tablets, smart wearable devices, large-size applications such as televisions, VR, micro-displays, and automotive central control screens or automotive taillights.

[0158] Preparation of the compounds of the present invention

[0159] Example

[0160] The present invention will now be described in detail with reference to the accompanying drawings and embodiments.

[0161] I. Synthesis of Intermediate 1:

[0162]

[0163] 3-Bromo-5-iodoaminobenzene (5 g, 16.8 mmol), 3,5-bis(trifluoromethyl)phenylboronic acid (3.87 g, 15.0 mmol), Pd(OAc)₂ (101 mg, 0.450 mmol), PPh₃ (239 mg, 0.911 mmol), and K₂CO₃ (6.23 g, 45.1 mmol) were added to a 200 mL double-necked round-bottom flask. Toluene (40 mL) and water (40 mL) were added via syringe, and the mixture was refluxed and reacted at 100 °C for 24 h. The resulting mixture was extracted with ethyl acetate (30 mL × 3). The combined organic layers were dried over Na₂SO₄ and concentrated under vacuum. The residue was subjected to silica gel column chromatography (eluent: hexane) to give intermediate 1. LC-MS: 383.72 ([M+H)₂) + Precision quality: 382.97.

[0164] II. Synthesis of Intermediate 2:

[0165]

[0166] In a three-necked flask under nitrogen protection, intermediate 1 (1.15 g, 3 mmol), pinacol diboronate (1.52 g, 6 mmol), NaOAc (1 g, 12 mmol), and Pd(PPh)₂Cl₂ (10.5 g, 1.5 mmol) were added sequentially to 5 mL of DMF. The mixture was stirred in a 90 °C oil bath for 8 h. Hexane and ethyl acetate were used as eluents, and the reaction progress was monitored by thin-layer chromatography. After the reaction was complete, the reaction system was cooled to room temperature and extracted with diethyl ether (10 mL × 3). The ether layer was washed three times with brine, dried over anhydrous magnesium sulfate, and purified by vacuum distillation using hexane and ethyl acetate (9:1) as eluents, yielding intermediate 2. LC-MS: Measured value: 432.19 ([M+H) + Precision quality: 431.15.

[0167] III. Synthesis of Intermediate 3:

[0168]

[0169] At room temperature, in an oven-dried round-bottom flask, a solution of hexafluoroglutaric anhydride (0.67 g, 3.0 mmol) and intermediate 2 (1.29 g, 3.0 mmol) were added to 30 mL of toluene solution, and the mixture was heated under reflux for 6 hours. The reaction mixture was cooled to room temperature and diluted with hexane (15 mL). The precipitated solid was filtered, washed with hexane, and dried under vacuum to obtain the crude product. The crude product was dissolved in 30 mL of Ac₂O, and NaOAc (3.69 g, 4.5 mmol) was added. The resulting mixture was stirred in an oil bath at 120 °C for 6 hours. After the reaction was complete, the mixture was quenched with cold water (30 mL) and extracted with dichloromethane (15 mL x 3). The combined organic layers were washed with saturated NaHCO₃ solution (30 mL x 2) and brine (20 mL). The organic layers were dried with anhydrous MgSO₄, filtered, and concentrated under vacuum. The crude product was purified by column chromatography (hexane / EtOAc, 7 / 3, silica gel) to obtain intermediate 3. LC-MS: Measured value: 636.31 ([M+H]) + Precision quality: 635.11.

[0170] IV. Synthesis of Intermediate 4:

[0171]

[0172] Intermediate 4 was prepared using the same method as intermediate 3, except that intermediate 2 was replaced with intermediate 1. LC-MS: Measured value: 587.75 ([M+H)). + Precision quality: 586.94.

[0173] V. Synthesis of Intermediate 5:

[0174]

[0175] Under Ar atmosphere, 1,3,5-tribromobenzene (9.6 g, 31 mmol) and Pd(PPh3)4 (1.0 g, 0.9 mmol) were added to a dry flask. A toluene (120 mL) solution of 3,5-bis(trifluoromethyl)phenylboronic acid (17 g, 66 mmol) and a 1 M Na2CO3 solution (100 mL) were added to the reaction vessel, and the mixture was refluxed under Ar for 48 h. The reaction mixture was cooled, evaporated, and extracted with EtOAc-H2O (1:1, 200 mL), and the aqueous layer was washed with EtOAc (3 × 100 mL). The combined organic phases were dried over Na2SO4 and concentrated under vacuum. The residue was purified by silica gel column chromatography, eluted with n-hexane, and recrystallized from CH2Cl2-n-hexane to give intermediate 5. LC-MS: Measured value: 580.60 ([M+H) + Precision quality: 579.97.

[0176] VI. Synthesis of Intermediate 6:

[0177]

[0178] Intermediate 6 was prepared using the same method as intermediate 1, except that 3-bromo-5-iodoaminobenzene was replaced with 2-bromo-4-iodoaniline (5 g, 16.8 mmol), and the reaction conditions were adjusted from 100 °C for 24 hours to 80 °C for 3 days. LC-MS: Measured value: 383.52 ([M+H)). + Precision quality: 382.97.

[0179] VII. Synthesis of Intermediate 7:

[0180]

[0181] In a three-necked flask under nitrogen protection, intermediate 6 (0.19 g, 0.5 mmol), a dioxane solution (50 mL) of pinacol diboronate (3.81 g, 15 mmol), Et3N (2.2 mL, 15 mmol), and PdCl2 (dppf) (0.22 g, 0.25 mmol) were added sequentially. The mixture was stirred in an oil bath at 100 °C for 3 h. After the reaction was complete, the reaction system was cooled to room temperature and quenched by adding 50 mL of H2O. The aqueous layer was extracted with EtOAc (50 mL × 3), and the combined organic layers were dried over anhydrous magnesium sulfate and concentrated under vacuum. Intermediate 7 was purified by silica gel column chromatography using petroleum ether / EtOAc (20 / 1) as the eluent. LC-MS: Measured value: 432.19 ([M+H) + Precision quality: 431.15.

[0182] VIII. Synthesis of Intermediate 8:

[0183]

[0184] Intermediate 8 was prepared using the same method as intermediate 3, except that intermediate 2 was replaced with intermediate 7 (1.29 g, 3.0 mmol). LC-MS: Measured value: 636.34 ([M+H]). + Precision quality: 635.11.

[0185] IX. Synthesis of Intermediate 9:

[0186]

[0187] Intermediate 9 was prepared using the same method as intermediate 3, except that intermediate 2 was replaced with intermediate 6 (1.15 g, 3.0 mmol). LC-MS: Measured value: 587.82 ([M+H]). + Precision quality: 586.94.

[0188] Synthesis of Intermediate X, 10:

[0189]

[0190] Under Ar atmosphere, 1,2-diiodo-4-bromobenzene (12.67 g, 31 mmol) and Pd(PPh3)4 (1.0 g, 0.9 mmol) were added to a dry flask. A toluene (120 mL) solution of 3,5-bis(trifluoromethyl)phenylboronic acid (17 g, 66 mmol) and a 1 M Na2CO3 solution (100 mL) were added to the reaction vessel, and the mixture was refluxed under Ar atmosphere for 48 h. The reaction mixture was cooled, quenched with 1 M hydrochloric acid aqueous solution, extracted with toluene, washed with water, dried over Na2SO4, and concentrated under vacuum. The residue was purified by silica gel column chromatography with n-hexane as eluent to give intermediate 10. Analytical value: 580.70 ([M+H) + Precision quality: 579.97.

[0191] XI. Synthesis of Intermediate 11:

[0192]

[0193] In a three-necked flask under nitrogen protection, tripinal ester of 1,3,5-phenyltriboronic acid (1.46 g, 3.2 mmol), 2-bromo-3,5-ditrifluoromethylaniline (3.08 g, 10.0 mmol), Pd(dppf)Cl2 (130 mg, 0.1 mmol), and Na2CO3 (3.30 g, 31.5 mmol) were dissolved in a mixture of THF / water (50 mL / 20 mL). The mixture was heated to 70 °C and stirred overnight. After cooling to room temperature, a saturated solution of ammonium chloride (100 mL) was added, and the organic layer was extracted with dichloromethane (4 x 50 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by rapid chromatography on silica gel (petroleum ether / ethyl acetate 9 / 1) to give intermediate 11. Analytical value: 760.44 ([M+H) + Precision quality: 759.10.

[0194] XII. Synthesis of Intermediate 12:

[0195]

[0196] Intermediate 12 was prepared according to the method for intermediate 11, except that the starting material 2-bromo-3,5-ditrifluoromethylaniline was replaced with 3-amino-5-bromotrifluorotoluene (2.40 g, 10.0 mmol). LC-MS: Measured value: 556.45 ([M+H)). + Precision quality: 555.14.

[0197] XIII. Synthesis of Intermediate 13:

[0198]

[0199] 3,3′,5,5′-tetrabromo-1,1′-biphenyl (0.5 g, 1.1 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)-3-(trifluoromethyl)aniline (1.52 g, 5.3 mmol), Pd(PPh3)4 (0.1 g, 0.1 mmol), and Cs2CO3 (2.8 g, 8.5 mmol) were added to a flask containing 1,4-dioxane / water (30 mL / 3 mL). The mixture was heated at 90 °C under nitrogen for 3 days. After cooling to room temperature, the solvent was removed under reduced pressure. The residue was then dissolved in CH2Cl2, washed with water and brine, and dried over anhydrous Na2SO4. Subsequently, the solvent was evaporated under reduced pressure, and the crude product was purified by column chromatography with CH2Cl2 / ethyl acetate as eluent, followed by silica gel column chromatography to give intermediate 13. LC-MS: Measured value: 791.31 ([M+H]) + ), Precision quality: 790.20.

[0200] XIV. Synthesis of Intermediate 14:

[0201]

[0202] Intermediate 14 was prepared according to the method for intermediate 13, except that the starting material 4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)-3-(trifluoromethyl)aniline was replaced with 3-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)-4-(trifluoromethyl)aniline. LC-MS: Measured value: 791.36 ([M+H)) + ), Precision quality: 790.20.

[0203] Synthesis of XV. Intermediate 15:

[0204]

[0205] Intermediate 15 was prepared according to the method for intermediate 11, except that 1,3,5-phenyltriboronic acid tripinal ester and 2-bromo-3,5-ditrifluoromethylaniline were replaced with 2,4,6-trifluoro-1,3,5-tribromobenzene (1.18 g, 3.2 mmol) and [3-amino-5-(trifluoromethyl)phenyl]boronic acid (2.03 g, 10.0 mmol). LC-MS: Measured value: 610.18 ([M+H) + Precision quality: 609.11.

[0206] XVI. Synthesis of Intermediate 16:

[0207]

[0208] Intermediate 16 was prepared according to the method for intermediate 11, except that the starting materials 1,3,5-phenyltriboronic acid tripinal ester and 2-bromo-3,5-ditrifluoromethylaniline were replaced with 2,4,6-tribromo-1,3,5-trimethylbenzene (1.14 g, 3.2 mmol) and [3-amino-5-(trifluoromethyl)phenyl]boronic acid (2.03 g, 10.0 mmol). LC-MS: Measured value: 598.24 ([M+H) + Precision quality: 597.18.

[0209] XVII. Synthesis of Intermediate 17:

[0210]

[0211] Intermediate 17 was prepared according to the method for intermediate 11, except that the starting material 2-bromo-3,5-ditrifluoromethylaniline was replaced with 3-bromo-4-trifluoromethylaniline (2.40 g, 10.0 mmol). LC-MS: Measured value: 556.31 ([M+H]). + Precision quality: 555.14.

[0212] Preparation of the compounds of the present invention

[0213] Example 1: Synthesis of Compound 4:

[0214]

[0215] In a three-necked flask under nitrogen protection, intermediates 3 (1.9 g, 3 mmol) and 4 (1.76 g, 3 mmol) were added sequentially, followed by 15 mL of 2 M Na₂CO₃. Pd(PPh₃)₄ (3.47 g, 3 mmol) was added to 100 mL of a 2:1 mixture of toluene and ethanol. The mixture was refluxed in an oil bath for 10 h. After the reaction was complete, the reaction system was cooled to room temperature, and the organic layer was separated by adding water (30 mL) and dichloroethylene (30 mL). The organic layer was washed three times with water, dried over anhydrous magnesium sulfate, and purified by vacuum distillation using hexane and dichloroethylene (5:1) as eluents, followed by silica gel column chromatography to obtain compound 4. LC-MS: Measured value: 1017.19 ([M+H) + Precision quality: 1016.04.

[0216] Synthetic Examples 2-4 were prepared using the same method as Synthetic Example 1, and Synthetic Examples 5-12 were prepared using the same method as Synthetic Intermediate 3, except that different raw materials M, N, intermediate A, and C were used. The raw materials and intermediates used in the synthesis process are shown in Table 1 below.

[0217] Table 1

[0218]

[0219]

[0220]

[0221] IV. Methods for determining the physical properties of compounds: The refractive index n and extinction coefficient k (with an isotropic glass substrate) were measured using an ellipsometer (JAWoollam Co., USA, model: ALPHA-SE) (tested under atmospheric conditions); All test results obtained using the above methods are shown in Table 2 below.

[0222] Table 2

[0223]

[0224] As can be seen from the data in Table 2 above, the refractive index of the compound of the present invention in the blue light region is less than 1.6; even less than 1.5.

[0225] V Device Examples

[0226] The following device examples further illustrate the beneficial technical effects of applying the compounds of the present invention as a capping layer in OLED devices.

[0227] 1. Materials, equipment, and testing methods used in the embodiments

[0228] Materials sourced from commercial purchases or synthesized independently by referencing existing technical literature.

[0229] The molecular structural formulas of the relevant materials are shown below:

[0230]

[0231]

[0232] equipment:

[0233] Vacuum Evaporation Equipment: Choshu Sangyo 200*200mm Vacuum Evaporation Equipment (Japan)

[0234] Test method:

[0235] Measurement of current efficiency, CIEx, CIEy, and perceptible color difference (JNCD):

[0236] Using an IVL (current-voltage-luminance) testing system (Suzhou Fostec Scientific Instruments Co., Ltd.), and selecting software EILV20060707, the OLED devices in the following device examples and comparative examples were tested. Data such as IVL characteristic curves, efficiency versus current density curves, and color coordinate positions were obtained. The tests must be conducted in a dark environment under a masking device. (At @10mA / cm) 2 The data under the specified conditions shall prevail (i.e., the test current density reaches 10 mA / cm²). 2 (corresponding performance values ​​at that time).

[0237] Structure and fabrication method of device embodiment 1:

[0238] Structure of Device Example 1: Substrate layer 100 / First electrode (anode) layer 200 (Ag (100nm)) / Hole injection layer 310 (HT-1:P-1 = 97:3 mass ratio, thickness 10nm) / Hole transport layer 320 (HT-1, thickness 117nm) / Electron blocking layer 330 (EB-1, thickness 10nm) / Light emitting layer 340 (BH-1:BD-1 = 97:3 mass ratio, thickness 20nm) / Hole blocking layer 350 (HB-1, thickness 8nm) / Electron transport layer 360 (ET-1:LiQ = 1:1 mass ratio, thickness 30nm) / Electron injection layer 370 (LiF, thickness 1nm) / Second electrode (cathode) layer 400 (Mg:Ag = 1:9 mass ratio, thickness 16nm) / First capping layer 510 (Compound 4 of the present invention, thickness 15nm) / Second capping layer 520 (CP-H1, thickness 50nm).

[0239] Fabrication method of device embodiment 1: The transparent substrate layer 100 is transparent glass, and the first electrode (anode) layer 200 is Ag (100nm). The first electrode (anode) layer 200 is washed, i.e., it is washed with alkali, washed with pure water, dried, and then washed with ultraviolet light and ozone to remove organic residues on the surface of the anode layer. On the anode layer 2 after the above washing, HT-1 and P-1 with a thickness of 10nm are deposited as hole injection layer 310 using a vacuum evaporation apparatus, with a mass ratio of HT-1 to P-1 of 97:3. Then, HT-1 with a thickness of 117nm is deposited as hole transport layer 320. Subsequently, EB-1 with a thickness of 10nm is deposited as electron blocking layer 330. After the above electron blocking material is deposited, the light-emitting layer 340 of the OLED light-emitting device is fabricated. Its structure includes BH-1 as the main material and BD-1 as the dopant material, with a doping ratio of 3% by weight, and the thickness of the light-emitting layer is 20nm. Following the aforementioned light-emitting layer 340, HB-1 is deposited to a thickness of 8 nm, serving as a hole-blocking layer 350. Above the hole-blocking layer 350, ET-1 and Liq are deposited at a mass ratio of 1:1. The vacuum-deposited film of this material is 30 nm thick, forming an electron transport layer 360. On the electron transport layer 360, a 1 nm thick LiF layer is formed using a vacuum deposition apparatus, serving as an electron injection layer 370. On the electron injection layer 370, a 16 nm thick Mg:Ag electrode layer is formed using a vacuum deposition apparatus, with a Mg:Ag mass ratio of 1:9, serving as a second electrode (cathode) layer 400. On the cathode layer, a 15 nm thick compound 4 of the present invention is vacuum-deposited as a first capping layer; on the first capping layer, a 50 nm thick CP-H1 layer is vacuum-deposited as a second capping layer.

[0240] Blue light device examples 2-12

[0241] The device structure and fabrication method are similar to those of Device Example 1, except that the materials of the first and second cover layers are changed; the specific cover layer materials are described in Table 3 below.

[0242] Comparative Examples of Blue Light Devices 1-3, 8

[0243] The structures and fabrication methods of the blue light devices in Comparative Examples 1 to 3 and 8 are similar to those in Example 1, except that a single-layer cover layer is used instead of a double-layer cover layer. The specific cover layer materials and film thicknesses are described in Table 3 below.

[0244] Comparative Examples of Blue Light Devices 4-7

[0245] The devices in Comparative Examples 4 to 7 are similar in structure and fabrication method to those in Example 1, except that a comparative compound is used as the first capping layer material. The specific capping layer materials are described in Table 3 below.

[0246] The test data for the material of the capping layer in the OLED device, the current efficiency of the device, CIEy, and perceptible color difference are listed in Table 3.

[0247] Table 3

[0248]

[0249]

[0250] Note: Index = Current efficiency / CIEy, and is only applied to blue light devices. The efficiency of blue light devices is generally not determined by current efficiency, but by Index (industry standard); perceptible color difference, unit: JNCD; 1 JNCD = 0.004.

[0251] The data in Table 3 show that, compared with Comparative Example 1, a blue OLED device using the compound of the present invention as a dual-layer capping layer with a low refractive index first capping layer and a high refractive index second capping layer, the index of the blue OLED device is increased by 7% to 12%. Furthermore, the color difference is significantly reduced at angles of 30°, 45°, and 60°, with some even reduced by 51% at 30° (device example 11). Therefore, the angle change is smaller, and the color shift effect is significantly improved.

[0252] Compared to Comparative Example 2, a blue OLED device with only a low-refractive-index capping layer, the index of the blue OLED device using the compound of the present invention as a dual-layer capping layer with a low-refractive-index first capping layer and a high-refractive-index second capping layer is increased by 56% to 65%. Furthermore, the color difference is significantly reduced at angles of 30°, 45°, and 60°, with some even reduced by 37% at 30° (device example 11). Therefore, the angle variation is smaller, and the color shift effect is significantly improved.

[0253] Compared to Comparative Example 3, a blue OLED device with only a low-refractive-index capping layer of the comparative compound CP-R1, the index of the blue OLED device using the compound of the present invention as a low-refractive-index first capping layer and a high-refractive-index second capping layer is increased by 72% to 82%. Furthermore, the color difference is significantly reduced at angles of 30°, 45°, and 60°, and in some cases even by 35% at 45° (device example 10). Therefore, the angle change is smaller and the color shift effect is significantly improved.

[0254] Compared with Comparative Example 4, which uses a double-layer capping layer with the compound CP-R1, the blue OLED device using the compound of the present invention as a double-layer capping layer with a low refractive index first capping layer and a high refractive index second capping layer has an index increase of 5% to 10%; and the color difference is significantly reduced at angles of 30°, 45° and 60°, some even by 37%@30° (device example 11), so the angle change is smaller and the color shift effect is significantly improved.

[0255] Compared with Comparative Example 5, which uses a double-layer capping layer with the compound CP-R2, the blue OLED device using the compound of the present invention as a double-layer capping layer with a low refractive index first capping layer and a high refractive index second capping layer has an index increase of 4% to 10%; and the color difference is significantly reduced at angles of 30°, 45° and 60°, some even by 40% at 30° (device example 11), thus the angle change is smaller and the color shift effect is significantly improved.

[0256] Compared with Comparative Example 6, which uses a double-layer capping layer with the compound CP-R3, the blue OLED device using the compound of the present invention as a double-layer capping layer with a low refractive index first capping layer and a high refractive index second capping layer has an index increase of 4% to 10%; and the color difference is significantly reduced at angles of 30°, 45° and 60°, some even by 35%@60° (device example 11), so the angle change is smaller and the color shift effect is significantly improved.

[0257] Compared to Comparative Example 7, which uses a double-layer capping layer with the compound CP-R4, the blue OLED device using the compound of the present invention as a low-refractive-index first capping layer and a high-refractive-index second capping layer has an index increase of 7%-9%. Furthermore, the color difference is significantly reduced at angles of 30°, 45°, and 60°, with some even reducing it by 30% at 60° (device example 3, where the second capping layer is CP-H12). Therefore, the angle variation is smaller, and the color shift effect is significantly improved.

[0258] Compared to Comparative Example 8, which only has a high refractive index capping layer, the blue OLED device using the compound of the present invention as a dual-layer capping layer with a low refractive index first capping layer and a high refractive index second capping layer has an index increase of 8%-10%; and the color difference is significantly reduced at angles of 30°, 45°, and 60°, with some even reducing it by 53%@60° (device example 3, where the second capping layer is CP-H12). Therefore, the angle change is smaller and the color shift effect is significantly improved.

[0259] It should be understood that the smaller the perceptible color difference and the smaller the amount of color change, the better the angle dependence of the emitted light wavelength of the organic electroluminescent device is suppressed.

[0260] In summary, the compound of the present invention, used as the first capping layer material in combination with a high refractive index second capping layer, forms a double capping layer that, when applied to OLED devices, significantly improves light extraction efficiency, current efficiency, and angle dependence, while maintaining excellent device light extraction efficiency and apparent polarization performance at high temperatures.

[0261] In summary, the above are merely preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. An organic compound containing a polyfluorinated glutarimide or succinimide, characterized in that, The structures of the polyfluorinated glutarimide or succinimide organic compounds are shown in general formula (1-1) or general formula (1-2): General formula (1-1) General formula (1-2) In general formulas (1-1) and (1-2), each occurrence of Z, whether identical or different, independently represents CR; Z at connections with other groups is represented by C. In general formula (1-1), L1, L2, and L3 each independently represent substituted or unsubstituted phenylene, substituted or unsubstituted diphenylene, or substituted or unsubstituted naphthylene. In general formula (1-2), L1, L2, and L3 each independently represent a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted diphenylene, or a substituted or unsubstituted naphthylene. Ar1 represents the structure shown in general formula (2); Ar2 and Ar3 are each independent structures shown in general formula (2) or general formula (3); General formula (2) General formula (3) The general formula (2) is expressed as: or ; Each of the R, R5 to R9, whether the same or different, independently represents a cyano group, a hydrogen atom, a deuterium atom, a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group, a difluoromethyl group, a difluoromethoxy group, a fluoromethyl group, a fluoromethoxy group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, or a tert-butoxy group. The substituents in the "substituted or unsubstituted" designation are selected from deuterium, halogen, cyano, trifluoromethyl, trifluoromethoxy, difluoromethyl, difluoromethoxy, fluoromethyl, fluoromethoxy, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, phenyl, diphenyl, terphenyl, naphthyl, etc. , , , , , , , , , , , , , , or .

2. The organic compound containing polyfluorinated glutarimide or succinimide according to claim 1, characterized in that, The structures of the polyfluorinated glutarimide or succinimide organic compounds are shown in general formulas (1-3) to (1-6): General formula (1-3) General formula (1-4) General formula (1-5) General formula (1-6) In general formulas (1-3) to (1-6), Z, L1, L2, L3, Ar1, Ar2, and Ar3 are defined in the same way as in general formula (1-2).

3. The organic compound containing polyfluorinated glutarimide or succinimide according to claim 1 or 2, characterized in that, Ar2 and Ar3 can be represented by any of the following structures: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 。 4. The polyfluorinated glutarimide or succinimide organic compound according to claim 1, 2 or 3, characterized in that, In the general formula (1-1), L1, L2, and L3 are represented as follows: or ; In the general formula (1-2), L1, L2, and L3 are represented as single bond, or .

5. An organic compound containing a polyfluorinated glutarimide or succinimide, characterized in that, The organic compound has a specific structural formula of any of the following: (1) (2) (3) (4) (5) (6) (7) (8) (9) (10) (11) (12) (13) (14) (15) (16) (17) (18) (19) (20) (21) (22) (23) (24) (25) (26) (27) (28) (29) (30) (31) (32) (33) (34) (35) (36) (37) (38) (39) (40) (41) (42) (43) (44) (45) (46) (47) (48) (49) (50) (51) (52) (53) (54) (55) (56) (57) (58) (59) (60) (61) (62) (63) (64) (65) (66) (67) (68) (69) (70) (71) (72) (73) (74) (75) (76) (77) (78) (79) (80) (81) (82) (83) (84) (85) (87) (88) (89) (90) (91) (92) (93) (94) (95) (96) (97) (98) (99) (100) (101) (102) (103) (104) (105) (106) (107) (108) (109) (110) (111) (112) (113) (114) (115) (116) (117) (118) (119) (120) (121) (122) (123) (124) (125) (126) (127) (128) (129) (130) (131) (132) (133) (134) (135) (136) (137） (138) (139) (140) (141) (142) (143) (144) (145) (146) (147) (148) (149) (150) (151) (152) (153) (154) (155) (156) (157) (158) (159) (160) (161) (162) (163) (164) (165) (166) (167) (168) (169) (170) (171) (172) (173) (174) (176) (177) (178) (180) (181) (182) (183) (184) (185) (186) (187) (188) (189) (190) (191) (192) (193) (194) (195) (196) (197) (198) (199) (200) (201) (202) (203) (204) (205) (206) (207) (208) (209) (210) (211) (212) (213) (214) (215) (216) (217) (218) (219) (220) (221) (222) (223) (224) (225) (226) (227) (228) (229) (230) (231) (232) (233) (234) (235) (236) (237) (238) (239) (240) (241) (242) (243) (244) (245) (246) (247) (248) (249) (250) (251) (252) (253) (254) (255) (256) (257) (258) (259) (260) (261) (262) (263) (264) (265) (266) (267) (268) (269) (270) (271) (272) (273) (274) (275) (276) (277) (278) (279) (280) (281) (282) (283) (284) (285) 。 6. The organic compound containing a polyfluorinated glutarimide or succinimide according to claim 1, characterized in that, The refractive index of the organic compound under blue light at a wavelength of 460 nm ranges from 1.4 to 1.

6.

7. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes: Substrate layer; A first electrode, which is on the substrate layer; An organic light-emitting functional layer is disposed on the first electrode; A second electrode, which is situated on the organic light-emitting functional layer; and A capping layer is applied over the second electrode; The cover layer includes a first cover layer and a second cover layer. The first covering layer is on top of the second electrode; The second cover layer is on top of the first cover layer; The first covering layer is characterized in that it comprises one or more of the polyfluorinated glutarimide or succinimide organic compounds as described in any one of claims 1-6. The refractive index of the first capping layer material is less than that of the second capping layer material. The refractive index of the first capping layer material at a wavelength of 460 nm is less than or equal to 1.60, and the refractive index of the second capping layer material at a wavelength of 460 nm is greater than or equal to 1.

85.

8. The organic electroluminescent device according to claim 7, characterized in that, The difference in refractive index between the second capping layer material and the first capping layer material at a wavelength of 460 nm is greater than or equal to 0.

3.

9. The organic electroluminescent device according to claim 7, characterized in that, The band gap Eg of the first capping layer material is greater than 3.0 eV, and the difference in refractive index between the first capping layer material at wavelengths of 460 nm and 620 nm is less than or equal to 0.

3.

10. The organic electroluminescent device according to claim 7, characterized in that, The band gap Eg of the first capping layer material is greater than 3.5 eV, and the difference in refractive index between the first capping layer material at wavelengths of 460 nm and 620 nm is less than or equal to 0.3.

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