Organic compound, organic electronic device and display panel

Abstract

The invention relates to an organic compound, an organic electronic device and a display panel, the chemical structural formula of the organic compound is as follows: # imgabs0 #, the organic compound can be used as a light extraction layer material to be applied to a light extraction layer of the organic electronic device, and harmful light can be prevented from generating adverse effects on materials in the organic electronic device; and the visible light emitting efficiency of the organic electronic device can be effectively improved.

Description

Technical Field

[0001] The present application relates to the field of display technology, and in particular to an organic compound, an organic electronic device and a display panel. Background Art

[0002] Organic electroluminescent display devices are a type of self-luminous display device that generates excitons through the transfer and recombination of carriers between various functional layers, and emits light through organic compounds or metal complexes with high quantum efficiency. It has the characteristics of self-luminescence, high brightness, high efficiency, high contrast, and high responsiveness.

[0003] At present, the luminous efficiency of organic light-emitting diodes (OLEDs) has been greatly improved, but its internal quantum efficiency has approached the theoretical limit. Therefore, improving the light extraction efficiency has become an effective means to further improve the stability and current efficiency of the device, such as the accumulation of metal complexes in the emission layer and the matching of the refractive index between the functional layers. In 2001, Hung et al. covered the surface of the metal cathode with a layer of organic or inorganic compounds of about 50 nanometers (nm), and improved the performance of the device by controlling the thickness and refractive index. In 2003, Riel et al. tried to evaporate ZnSe, an inorganic compound with a high refractive index (n=2.6), on the cathode, and used the difference in refractive index between the functional layers to improve the light extraction efficiency. However, due to the high evaporation temperature and slow evaporation rate of inorganic materials, this type of compound has not been widely used in organic electroluminescent devices.

[0004] In view of the above reasons, it is possible to try to apply organic compounds with a higher refractive index to electroluminescent devices to improve light extraction efficiency. Such organic compounds must meet the following conditions: high extinction coefficient in the ultraviolet band (λ<400nm) to avoid the adverse effects of harmful light on device materials; extinction coefficient close to 0 in the visible light range (λ>430nm), high transmittance to visible light, and reduced impact on the light extraction efficiency of the device; high refractive index in the visible light range with small difference, with the characteristics of improving light extraction and optimizing device structure; high glass transition temperature to improve the thermal stability of the compound.

[0005] Therefore, a new class of materials that improve the light extraction efficiency of organic electroluminescent devices needs to be further developed. Summary of the invention

[0006] The embodiments of the present application provide an organic compound, an organic electronic device and a display panel. The organic compound can be used as a light extraction layer material in the light extraction layer of the organic electronic device, which can prevent harmful light from having an adverse effect on the materials inside the organic electronic device and can effectively improve the visible light extraction efficiency of the organic electronic device.

[0007] In order to achieve the above object, according to the first aspect of the present application, an organic compound is provided, and the chemical structural formula of the organic compound is shown in Formula 1:

[0008]

[0009] Wherein, Ar1 is selected from any one or a combination of the following groups:

[0010]

[0011] Y1, Y2, Y3, Y4, Y5, Y6, Y7 and Y8 are selected from N or CR4;

[0012] X is selected from CR5R6, C=C(R5R6), SiR5R6, NR5, C(=O), S, SO2, S(=O) or O;

[0013] Ar2 is selected from any one of the following groups:

[0014]

[0015] The dashed lines in Ar1 and Ar2 represent single bonds;

[0016] L1 is selected from a single bond, an alkenyl group, an alkynyl group, an acyl group, an amide group, a carbonyl group, a sulfone group, a substituted or unsubstituted alkyl group having 1 to 60 C atoms, a substituted or unsubstituted alkoxy group having 1 to 60 C atoms, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms;

[0017] R1, R2, R3, R4, R5 and R6 are selected from hydrogen, D, linear alkyl having 1 to 20 C atoms, linear alkoxy having 1 to 20 C atoms, linear thioalkoxy having 1 to 20 C atoms, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, branched or cyclic thioalkoxy having 3 to 20 C atoms, silyl, keto having 1 to 20 C atoms, alkoxycarbonyl having 2 to 20 C atoms, aryloxycarbonyl having 7 to 20 C atoms, cyano, At least one of carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, an aryloxy group having 5 to 60 ring atoms, and a heteroaryloxy group having 5 to 60 ring atoms; among the R1, R2, R3, R4, R5 and R6 groups, two or more adjacent groups can form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system.

[0018] In some embodiments, Ar2 is selected from any one of the following groups:

[0019]

[0020]

[0021] In some embodiments, the organic compound is selected from any one of the compounds represented by Formula 2-1 to Formula 2-9:

[0022]

[0023] In some embodiments, Ar1 is selected from any one or a combination of the following groups:

[0024]

[0025]

[0026] wherein the H atoms on the ring of the Ar1 group are not substituted or are substituted by R7;

[0027] R7 is selected from D, linear alkyl having 1 to 20 C atoms, linear alkoxy having 1 to 20 C atoms, linear thioalkoxy having 1 to 20 C atoms, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, branched or cyclic thioalkoxy having 3 to 20 C atoms, silyl, keto having 1 to 20 C atoms, alkoxycarbonyl having 2 to 20 C atoms, aryloxycarbonyl having 7 to 20 C atoms, cyano , carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, an aryloxy group having 5 to 60 ring atoms, and a heteroaryloxy group having 5 to 60 ring atoms; two or more adjacent R7 groups can form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system.

[0028] In some embodiments, the L1 is selected from a single bond or at least one of the following groups:

[0029]

[0030] Wherein, W is selected from N or CR8;

[0031] R8 is selected from hydrogen, D, linear alkyl having 1 to 20 C atoms, linear alkoxy having 1 to 20 C atoms, linear thioalkoxy having 1 to 20 C atoms, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, branched or cyclic thioalkoxy having 3 to 20 C atoms, silyl, keto having 1 to 20 C atoms, alkoxycarbonyl having 2 to 20 C atoms, aryloxycarbonyl having 7 to 20 C atoms, cyano R8 is a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, an aryloxy group having 5 to 60 ring atoms, or a heteroaryloxy group having 5 to 60 ring atoms; two or more adjacent R8 groups may form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system;

[0032] X1 is selected from CR5R6, C=C(R5R6), SiR5R6, NR5, C(=O), S, SO2, S(=O) or O.

[0033] In some embodiments, the organic compound is selected from any one of the compounds represented by Formula 3-1 to Formula 3-9:

[0034]

[0035] In some embodiments, the refractive index of the organic compound for light with a wavelength of 630 nm is greater than 1.7, and the extinction coefficient of the organic compound for light with a wavelength of 430 nm is less than 0.1.

[0036] In some embodiments, the singlet energy of the organic compound is greater than 2.7 eV.

[0037] According to a second aspect of the present application, an organic electronic device is provided, comprising:

[0038] First electrode:

[0039] a second electrode, arranged opposite to the first electrode;

[0040] an organic functional layer, located between the first electrode and the second electrode;

[0041] The light extraction layer is located on the side of the first electrode away from the organic functional layer, or on the side of the second electrode away from the organic functional layer. The material of the light extraction layer is at least one of the organic compounds mentioned above.

[0042] According to a third aspect of the present application, a display panel is also provided, wherein the display panel includes the organic electronic device described above.

[0043] In the organic compound, organic electronic device and display panel of the embodiments of the present application, the organic compound shown in Formula 1 is a triarylamine organic compound, and the chemical structure of the organic compound includes at least one of the large groups such as ortho-phenylnaphthobenzofuran group, phenanthrophenyloxazole group, diazadibenzothiophene or chrysene group. At the same time, the chemical structure of the organic compound also includes at least one phenylbenzoxazole group. The combination of these large groups enables the organic compound to have a higher glass transition temperature and thermal stability; and the organic compound contains a plurality of N atoms, which can enhance the electron-withdrawing ability of the group, improve the electron push-pull of the entire organic compound molecule, and is beneficial to regulating the energy level and dipole moment of the organic compound molecule, thereby facilitating the improvement of the ultraviolet absorption and molecular refractive index of the organic compound molecule below a wavelength of 400 nm, so that the organic compound has a high extinction coefficient in the ultraviolet band, a small extinction coefficient in the visible light range, and a higher refractive index. Therefore, the organic compound can be used as a light extraction layer material in the light extraction layer of an organic electronic device, which can prevent harmful light from having an adverse effect on the materials inside the organic electronic device and can effectively improve the visible light extraction efficiency.

[0044] Other features and advantages of the present application will be described in detail in the subsequent detailed description. BRIEF DESCRIPTION OF THE DRAWINGS

[0045] In order to more completely understand the present application and its beneficial effects, the following description will be given in conjunction with the accompanying drawings, wherein the same figure numbers represent the same parts in the following description.

[0046] Figure 1 It is a schematic diagram of the structure of an organic electronic device provided in an embodiment of the present application.

[0047] Figure numerals: 1, substrate; 2, first electrode (anode); 3, organic functional layer; 3a, hole injection layer; 3b, hole transport layer; 3c, light-emitting layer; 3d, electron transport layer; 3e, electron injection layer; 4, second electrode (cathode); 5, light extraction layer. DETAILED DESCRIPTION

[0048] The present application provides an aromatic amine organic compound and its application in an organic electronic device, in particular, as a light extraction layer material for an organic electroluminescent device. In order to make the purpose, technical solution and effect of the present application clearer and more specific, the present application is further described in detail below. It should be understood that the specific embodiments described herein are only used to explain the present application and are not used to limit the present application.

[0049] In the present application, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0050] In the present application, the "number of ring atoms" refers to the number of atoms in the atoms constituting the ring itself of a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) formed by atoms bonding to form a ring. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring atoms. The same is true for the "number of ring atoms" described below unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

[0051] In the present application, "adjacent groups" means that these groups are bonded to the same carbon atom or to adjacent carbon atoms. These definitions apply correspondingly to "adjacent substituents".

[0052] In the present application, an aromatic group refers to a hydrocarbon group containing at least one aromatic ring, and a heteroaromatic group refers to an aromatic hydrocarbon group containing at least one heteroatom. The heteroatom is preferably selected from Si, N, P, O, S and / or Ge, and is particularly preferably selected from Si, N, P, O and / or S. A condensed ring aromatic group refers to a ring of an aromatic group that can have two or more rings, wherein two carbon atoms are shared by two adjacent rings, i.e., a condensed ring. A condensed heterocyclic aromatic group refers to a condensed ring aromatic hydrocarbon group containing at least one heteroatom. For the purposes of the present invention, an aromatic group or a heteroaromatic group includes not only a system of aromatic rings, but also a non-aromatic ring system. Therefore, systems such as pyridine, thiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, pyrazine, pyridazine, pyrimidine, triazine, carbene, etc. are also considered to be aromatic groups or heterocyclic aromatic groups for the purposes of the invention. For the purposes of the present invention, fused aromatic or fused heteroaromatic ring systems include not only systems of aromatic or heteroaromatic groups, but also systems in which multiple aromatic or heteroaromatic groups may be interrupted by short non-aromatic units (<10% non-H atoms, preferably less than 5% non-H atoms, such as C, N or O atoms). Thus, systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamines, diaryl ethers, etc. are also considered fused aromatic ring systems for the purposes of this application.

[0053] The present application provides an organic compound, the chemical structure of which is shown in Formula 1:

[0054]

[0055] Wherein, Ar1 is selected from any one or a combination of the following groups:

[0056]

[0057] Y1, Y2, Y3, Y4, Y5, Y6, Y7 and Y8 are selected from N or CR4;

[0058] The dotted line in the group representing Ar1 above represents the bond connecting Ar1 and L1, and the bond is a single bond;

[0059] X is selected from CR5R6, C=C(R5R6), SiR5R6, NR5, C(=O), S, SO2, S(=O) or O;

[0060] Ar2 is selected from any one of the following groups:

[0061]

[0062] The dotted line in the group representing Ar2 above represents the bond connecting Ar2 to N, and C at any position on Ar2 can be connected to N through a single bond;

[0063] L1 is selected from a single bond, an alkenyl group, an alkynyl group, an acyl group, an amide group, a carbonyl group, a sulfone group, a substituted or unsubstituted alkyl group having 1 to 60 C atoms, a substituted or unsubstituted alkoxy group having 1 to 60 C atoms, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms;

[0064] R1, R2, R3, R4, R5 and R6 are selected from hydrogen, D, linear alkyl having 1 to 20 C atoms, linear alkoxy having 1 to 20 C atoms, linear thioalkoxy having 1 to 20 C atoms, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, branched or cyclic thioalkoxy having 3 to 20 C atoms, silyl, keto having 1 to 20 C atoms, alkoxycarbonyl having 2 to 20 C atoms, aryloxycarbonyl having 7 to 20 C atoms, cyano (-CN), carbamoyl (-C At least one of R1, R2, R3, R4, R5 and R6 groups; two or more adjacent groups may form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system.

[0065] In some embodiments, Y1-Y4 in the Ar1 group are all CH.

[0066] In some embodiments, Y1 or Y4 in the Ar1 group is N.

[0067] In some embodiments, at least two of Y1-Y4 in the Ar1 group are N.

[0068] In some embodiments, Y1 and Y4 in the Ar1 group are both N.

[0069] In some embodiments, Y5-Y8 in the Ar1 group are all CH.

[0070] In some embodiments, at least one of Y5-Y8 in the Ar1 group is N.

[0071] In some embodiments, at least two of Y5 to Y8 in the Ar1 group are N.

[0072] In some embodiments, Y5 and Y8 in the Ar1 group are both N.

[0073] It should be noted that the number of N atoms in Y1 to Y8 directly affects the electron-withdrawing ability of the Ar1 group, because the N atoms can enhance the electron-withdrawing ability of the Ar1 group and improve the electron push-pull of the entire organic compound molecule, which is beneficial to regulating the energy level and dipole moment of the organic compound molecule, thereby improving the ultraviolet absorption rate and molecular refractive index of the organic compound molecule at a wavelength of 400nm, so that the organic compound can be used as a light extraction layer material in an organic electronic device.

[0074] In some embodiments, Ar1 is selected from any one or a combination of the following groups:

[0075] wherein the H atoms on the ring of the Ar1 group are not substituted or are substituted by R7;

[0076] R7 is selected from D, linear alkyl having 1 to 20 C atoms, linear alkoxy having 1 to 20 C atoms, linear thioalkoxy having 1 to 20 C atoms, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, branched or cyclic thioalkoxy having 3 to 20 C atoms, silyl, keto having 1 to 20 C atoms, alkoxycarbonyl having 2 to 20 C atoms, aryloxycarbonyl having 7 to 20 C atoms, cyano , carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, an aryloxy group having 5 to 60 ring atoms, and a heteroaryloxy group having 5 to 60 ring atoms; two or more adjacent R7 groups can form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system.

[0077] In some embodiments, Ar2 is selected from any one of the following groups:

[0078]

[0079] In some preferred embodiments, Ar2 is selected from any one of the following groups:

[0080]

[0081] In some embodiments, the organic compound is selected from any one of the compounds represented by Formula 2-1 to Formula 2-9:

[0082]

[0083] In a preferred embodiment, Ar1 is selected from any one or a combination of two of the following groups:

[0084]

[0085] In a preferred embodiment, Ar1 is selected from any one or a combination of two of the following groups:

[0086]

[0087] In some embodiments, the L1 is selected from a single bond or at least one of the following groups:

[0088]

[0089] Wherein, W is selected from N or CR8;

[0090] R8 is selected from hydrogen, D, linear alkyl having 1 to 20 C atoms, linear alkoxy having 1 to 20 C atoms, linear thioalkoxy having 1 to 20 C atoms, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, branched or cyclic thioalkoxy having 3 to 20 C atoms, silyl, keto having 1 to 20 C atoms, alkoxycarbonyl having 2 to 20 C atoms, aryloxycarbonyl having 7 to 20 C atoms, cyano R8 is a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, an aryloxy group having 5 to 60 ring atoms, or a heteroaryloxy group having 5 to 60 ring atoms; two or more adjacent R8 groups may form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system;

[0091] X1 is selected from CR5R6, C=C(R5R6), SiR5R6, NR5, C(=O), S, SO2, S(=O) or O.

[0092] In some embodiments, L1 is selected from a single bond or any one or more combinations of the following groups:

[0093]

[0094]

[0095] It should be noted that the H atom in the cyclic group represented by L1 above may be further substituted.

[0096] In some embodiments, L1 is selected from any one or a combination of the following groups:

[0097] It should be noted that the H atom in the cyclic group represented by L1 above may be further substituted.

[0098] In some embodiments, the organic compound is selected from any one of the compounds represented by Formula 3-1 to Formula 3-9:

[0099]

[0100] In a preferred embodiment, the organic compound is selected from any one of the compounds represented by Formula 4-1 to Formula 4-9:

[0101]

[0102] In some embodiments, Y1-Y4 in the compounds represented by Formula 4-1 to Formula 4-9 are all CH.

[0103] In one embodiment, the organic compound is selected from any one of the following compounds:

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120] The H in the above-mentioned organic compounds may be further arbitrarily substituted, in particular deuterated.

[0121] In some embodiments, the glass transition temperature Tg of the organic compound represented by Formula 1 is ≥100°C. In a preferred embodiment, the glass transition temperature Tg of the organic compound represented by Formula 1 is ≥120°C. In another more preferred embodiment, the glass transition temperature Tg of the organic compound represented by Formula 1 is ≥140°C. In another more preferred embodiment, the glass transition temperature Tg of the organic compound represented by Formula 1 is ≥160°C. In a most preferred embodiment, the glass transition temperature Tg of the organic compound represented by Formula 1 is ≥180°C. It can be seen that the organic compound represented by Formula 1 has a higher glass transition temperature, which makes the organic compound have better thermal stability.

[0122] In some embodiments, the refractive index of the organic compound represented by Formula 1 for light with a wavelength of 630 nm is greater than 1.7. In a preferred embodiment, the refractive index of the organic compound represented by Formula 1 for light with a wavelength of 630 nm is greater than 1.78. In a more preferred embodiment, the refractive index of the organic compound represented by Formula 1 for light with a wavelength of 630 nm is greater than 1.83. It can be seen that the organic compound represented by Formula 1 has a higher refractive index for visible light.

[0123] In some embodiments, the singlet energy (S1) of the organic compound represented by Formula 1 is greater than or equal to 2.7 eV. In a preferred embodiment, the singlet energy (S1) of the organic compound represented by Formula 1 is greater than or equal to 2.8 eV. In a more preferred embodiment, the singlet energy (S1) of the organic compound represented by Formula 1 is greater than or equal to 2.85 eV. When the singlet energy (S1) of the organic compound represented by Formula 1 meets the above requirements, the refractive index and glass transition temperature of the organic compound can be increased, so that the organic compound has higher thermal stability.

[0124] In some embodiments, the extinction coefficient of the organic compound represented by Formula 1 for light with a wavelength of 430 nm is less than 0.1. In a preferred embodiment, the extinction coefficient of the organic compound represented by Formula 1 for light with a wavelength of 430 nm is less than 0.003. In a more preferred embodiment, the extinction coefficient of the organic compound represented by Formula 1 for light with a wavelength of 430 nm is less than 0.001. It can be seen that the organic compound represented by Formula 1 has a high transmittance to visible light, which can reduce its impact on the light output efficiency of the device.

[0125] In some embodiments, the extinction coefficient of the organic compound represented by Formula 1 for light with a wavelength of 350 nm is greater than or equal to 0.3. In a preferred embodiment, the extinction coefficient of the organic compound represented by Formula 1 for light with a wavelength of 350 nm is greater than or equal to 0.5. In a better preferred embodiment, the extinction coefficient of the organic compound represented by Formula 1 for light with a wavelength of 350 nm is greater than or equal to 0.7. In a more preferred embodiment, the extinction coefficient of the organic compound represented by Formula 1 for light with a wavelength of 350 nm is greater than or equal to 1.0. It can be seen that the organic compound represented by Formula 1 has a larger extinction coefficient in the ultraviolet band (λ<400nm).

[0126] As can be seen from the above, the organic compound represented by Formula 1 has a higher glass transition temperature, a higher refractive index for visible light, a higher transmittance for visible light, and a larger extinction coefficient in the ultraviolet band, and is very suitable as a material for the light extraction layer.

[0127] When the organic compound provided in the embodiment of the present application is applied to an evaporation-type OLED device, the molecular weight of the organic compound represented by Formula 1 is ≤1200 g / mol. In some preferred embodiments, the molecular weight of the organic compound represented by Formula 1 is ≤1100 g / mol. In some more preferred embodiments, the molecular weight of the organic compound represented by Formula 1 is ≤1000 g / mol. In some more preferred embodiments, the molecular weight of the organic compound represented by Formula 1 is ≤950 g / mol. In some most preferred embodiments, the molecular weight of the organic compound represented by Formula 1 is ≤900 g / mol.

[0128] When the organic compound provided in the embodiments of the present application is applied to a printed OLED device, the molecular weight of the organic compound represented by Formula 1 is ≥800 g / mol. In some preferred embodiments, the molecular weight of the organic compound represented by Formula 1 is ≥900 g / mol. In some more preferred embodiments, the molecular weight of the organic compound represented by Formula 1 is ≥1000 g / mol. In some more preferred embodiments, the molecular weight of the organic compound represented by Formula 1 is ≥1100 g / mol. In some most preferred embodiments, the molecular weight of the organic compound represented by Formula 1 is ≥1200 g / mol.

[0129] In some embodiments, at 25°C, the solubility of the organic compound represented by Formula 1 in toluene is ≥2 mg / ml. In some preferred embodiments, at 25°C, the solubility of the organic compound represented by Formula 1 in toluene is ≥3 mg / ml. In some more preferred embodiments, at 25°C, the solubility of the organic compound represented by Formula 1 in toluene is ≥4 mg / ml. In some most preferred embodiments, at 25°C, the solubility of the organic compound represented by Formula 1 in toluene is ≥5 mg / ml.

[0130] The present application also provides a composition, comprising at least one organic compound as described above and at least one organic solvent, wherein the organic solvent is selected from at least one of aromatic, heteroaromatic, ester, aromatic ketone, aromatic ether, aliphatic ketone, aliphatic ether, alicyclic, olefinic compound, boric ester and phosphate ester compounds.

[0131] In some embodiments, the organic solvent is selected from aromatic or heteroaromatic based solvents, in particular aliphatic chain / ring substituted aromatic solvents, or aromatic ketone solvents, or aromatic ether solvents.

[0132] Examples of organic solvents suitable for the present application include, but are not limited to: aromatic or heteroaromatic based solvents: p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-xylene, m-xylene, p-xylene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, 1-methoxynaphthalene, cyclohexylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4- trichlorobenzene, 1,3-dipropoxybenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, dibenzyl ether, etc.; ketone-based solvents: 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone , 3-methylpropiophenone, 2-methylpropiophenone, isophorone, 2,6,8-trimethyl-4-nonanone, fenchone, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, phorone, di-n-amyl ketone; aromatic ether solvents: 3-phenoxytoluene, butoxybenzene, benzylbutylbenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethyl ethyl ether, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxy Benzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether, amyl ether c-hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether; ester solvents: alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc.

[0133] In some embodiments, the organic solvent can be selected from: aliphatic ketones, for example, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, phorone, di-n-amyl ketone, etc.; or aliphatic ethers, for example, amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, etc.

[0134] In some other embodiments, the composition further comprises another organic solvent. Examples of another organic solvent include (but are not limited to): methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, indene and / or mixtures thereof.

[0135] In some embodiments, the composition is a solution.

[0136] In other embodiments, the composition is a suspension.

[0137] In some embodiments, the mass fraction of the organic compound in the composition ranges from 0.01wt% to 20wt%. In a preferred embodiment, the mass fraction of the organic compound in the composition ranges from 0.1wt% to 15wt%. In a more preferred embodiment, the mass fraction of the organic compound in the composition ranges from 0.2wt% to 10wt%. In a most preferred embodiment, the mass fraction of the organic compound in the composition ranges from 0.25wt% to 5wt%.

[0138] For example, the mass fraction of the organic compound in the composition is 0.01wt%, 0.20wt%, 0.30wt%, 0.40wt%, 0.50wt%, 0.60wt%, 0.70wt%, 0.80wt%, 0.90wt%, 1wt%, 3wt%, 5wt%, 8wt%, 10wt%, 12wt%, 15wt%, 18wt% or 20wt%.

[0139] The present application also provides a use of the composition as a coating or printing ink in the preparation of an organic electronic device. In a preferred embodiment, the composition is used as a coating or printing ink in a method for preparing an organic electronic device by printing or coating.

[0140] Among them, suitable printing or coating techniques include (but not limited to) inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, blade coating, roller printing, twist roller printing, lithography, flexographic printing, rotary printing, spraying, brushing, pad printing, slit extrusion coating, etc. Preferred are gravure printing, nozzle printing and inkjet printing. The solution or suspension may further include one or more components such as surfactant compounds, lubricants, wetting agents, dispersants, hydrophobic agents, adhesives, etc., for adjusting viscosity, film-forming properties, improving adhesion, etc. For relevant printing techniques and their related requirements for relevant solutions, such as solvents and concentrations, viscosities, etc., please refer to "Handbook of Print Media: Technologies and Production Methods" edited by Helmut Kipphan, ISBN 3-540-67326-1.

[0141] An embodiment of the present application further provides an organic electronic device, wherein the material of the organic electronic device comprises at least one of the organic compounds or the mixture described above, or the organic electronic device is prepared from the composition described above.

[0142] The organic electronic device can be selected from organic light-emitting diodes (OLED), organic photovoltaic cells (OPV), organic light-emitting cells (OLEEC), organic field-effect transistors (OFET), organic light-emitting field-effect transistors (OLEFET), organic lasers, organic spintronic devices, organic sensors, and organic plasmon emitting diodes (OPED), etc. Particularly preferably, the organic electronic device is an organic electroluminescent device, such as OLED, OLEEC, OFET or OLEFET.

[0143] In some embodiments, the organic compound is at least one of an electron transport layer material, a light emitting layer host material, and a light extraction layer material of an organic electronic device.

[0144] In a specific embodiment, Figure 1As shown, the organic electronic device includes a substrate 1, a first electrode 2 located on the substrate 1, a second electrode 4 arranged opposite to the first electrode 2, an organic functional layer 3 located between the first electrode 2 and the second electrode 4, and a light extraction layer 5 located on the side of the first electrode 2 or the second electrode 4 away from the organic functional layer 3; the material of the light extraction layer 5 is the organic compound mentioned above.

[0145] In a preferred embodiment, the organic electronic device is an OLED device, for example, the first electrode 2 is an anode, the second electrode 4 is a cathode, the organic functional layer 3 includes at least one light-emitting layer, and the light extraction layer 5 is located on the side of the cathode 4 away from the organic functional layer 3.

[0146] In some embodiments, Figure 1 The organic functional layer 3 shown includes a hole injection layer 3a, a hole transport layer 3b, a light emitting layer 3c, an electron transport layer 3d and an electron injection layer 3e, but is not limited thereto.

[0147] Of course, in other embodiments, the light extraction layer may also be located on the side of the anode away from the organic functional layer.

[0148] In some embodiments, the material of the light extraction layer of the organic electronic device comprises any one or more combinations of the compounds represented by the aforementioned formula (2-1) to formula (2-9).

[0149] In other embodiments, the material of the light extraction layer of the organic electronic device comprises any one or more combinations of the compounds represented by the aforementioned formula (3-1) to formula (3-9).

[0150] In other embodiments, the material of the light extraction layer of the organic electronic device comprises any one or more combinations of the compounds represented by the aforementioned formulae (4-1) to (4-9).

[0151] In the embodiment of the present application, since the organic compound shown in Formula 1 has a higher glass transition temperature, the thermal stability of the light extraction layer is better; since the organic compound shown in Formula 1 has a higher refractive index for visible light, the light extraction rate of the light extraction layer is higher, thereby improving the light efficiency of the organic light-emitting device, especially helping to improve the external light-emitting efficiency. In addition, the singlet energy (S1) of the organic compound shown in Formula 1 is greater than or equal to 2.7 eV, which is beneficial to improve the refractive index, glass transition temperature and thermal stability of the organic compound, thereby improving the light extraction rate and stability of the light extraction layer. In addition, the extinction coefficient of the organic compound shown in Formula 1 for light with a wavelength of 430 nm is less than 0.1, so that the extinction coefficient of the light extraction layer in the visible light band is smaller, so that the light extraction layer has a higher transmittance for visible light, which can reduce its impact on the light extraction efficiency of the device. Furthermore, the organic compound shown in Formula 1 has a larger extinction coefficient in the ultraviolet band (λ<400nm), which can prevent harmful light from having an adverse effect on the materials inside the organic electronic device.

[0152] The device structure of the organic electroluminescent device, such as the cathode, the anode and the light extraction layer, is described in detail below, but is not limited thereto.

[0153] The anode may comprise a conductive metal, metal oxide or conductive polymer. The anode can easily inject holes into the hole injection layer (HIL) or the hole transport layer (HTL) or the light-emitting layer. In some embodiments, the absolute value of the difference between the work function of the anode and the HOMO level or valence band level of the light emitter in the light-emitting layer or the p-type semiconductor material as the HIL or HTL or the electron blocking layer (EBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. Examples of anode materials include but are not limited to: Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), etc. Other suitable anode materials are known and can be easily selected for use by a person of ordinary skill in the art. The anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc. In some embodiments, the anode is patterned. The patterned ITO conductive substrate is commercially available and can be used to prepare the organic electroluminescent device of the embodiment of the present application.

[0154] The cathode may comprise a conductive metal or metal oxide. The cathode can easily inject electrons into the EIL or ETL or directly into the light-emitting layer. In some embodiments, the absolute value of the difference between the work function of the cathode and the LUMO energy level or conduction band energy level of the light-emitting body in the light-emitting layer or the n-type semiconductor material as the electron injection layer (EIL) or the electron transport layer (ETL) or the hole blocking layer (HBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials that can be used as cathodes of OLEDs may be used as cathode materials of the organic electroluminescent device of the present application. Examples of cathode materials include but are not limited to: Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The cathode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.

[0155] The light extraction layer has a suitable energy level structure, has strong absorption in the region with a wavelength less than 400nm (ultraviolet band), and has weak or close to zero absorption in the visible light band with a wavelength greater than 400nm, which can prevent the internal materials of the device from being damaged by high-energy light in the subsequent process. At the same time, the light extraction layer has a high refractive index, which can be beneficial to the emission of visible light, thereby improving the luminous efficiency of the organic electroluminescent device.

[0156] When the reflectivity of the interface between the light extraction layer and the adjacent electrode (for example) is large, the influence of light interference is large, so the refractive index of the material constituting the light extraction layer is preferably greater than the refractive index of the adjacent electrode. The refractive index of the light extraction layer material for light with a wavelength of 630nm is generally greater than or equal to 1.50. In a preferred embodiment, the refractive index of the light extraction layer material for light with a wavelength of 630nm is greater than or equal to 1.70. In a particularly preferred embodiment, the refractive index of the light extraction layer material for light with a wavelength of 630nm is greater than or equal to 1.80.

[0157] In some embodiments, the thickness of the light extraction layer ranges from 10nm to 200nm. In a preferred embodiment, the thickness of the light extraction layer ranges from 20nm to 150nm. In a more preferred embodiment, the thickness of the light extraction layer ranges from 30nm to 100nm. In a most preferred embodiment, the thickness of the light extraction layer ranges from 40nm to 90nm.

[0158] An embodiment of the present application further provides a display panel, which includes the organic electronic device described above.

[0159] The embodiments of the present application also provide an application of the above-mentioned organic electroluminescent device in various electronic devices, including but not limited to display devices, lighting devices, light sources, sensors, etc.

[0160] The present application will be described below in conjunction with preferred embodiments, but the present application is not limited to the embodiments described below. It should be understood that the attached claims summarize the scope of the present application. Under the guidance of the concept of the present invention, those skilled in the art should realize that certain changes made to the various embodiments of the present application will be covered by the spirit and scope of the claims of the present application. (I) Specific embodiments

[0162] The following is an example of the synthesis method of the organic compound provided in the examples of the present application, but the present application is not limited to the following examples.

[0163] Example 1

[0164] The synthetic route of organic compound M1 is as follows:

[0165]

[0166] Synthesis of compound M1:

[0167] The intermediate 1-1 (10 mmol), compound 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C under a nitrogen atmosphere for 6 hours (h); after cooling, the solvent was removed by rotary evaporation, the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M1 with a molar weight of 9.23 mmol and a yield of 92.3%; the atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M1 was: MS (ASAP) = 695.

[0168] Example 2

[0169] The synthetic route of organic compound M2 is as follows:

[0170]

[0171] Synthesis of organic compound M2:

[0172] The intermediate 1-1 (10 mmol), compound 2-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M2 with a molar weight of 8.65 mmol and a yield of 86.5%; the atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M2 was: MS (ASAP) = 696.

[0173] Example 3

[0174] The synthetic route of organic compound M3 is as follows:

[0175]

[0176] Synthesis of organic compound M3:

[0177] The intermediate 1-1 (10 mmol), compound 3-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M3 with a molar weight of 8.92 mmol and a yield of 89.2%; the atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M3 was: MS (ASAP) = 629.

[0178] Example 4

[0179] The synthetic route of organic compound M4 is as follows:

[0180]

[0181] Synthesis of organic compound M4:

[0182] The intermediate 1-1 (10 mmol), compound 4-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M4 with a molar weight of 8.76 mmol and a yield of 87.6%; the atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M4 was: MS (ASAP) = 629.

[0183] Example 5

[0184] The synthetic route of organic compound M5 is as follows:

[0185]

[0186] Synthesis of organic compound M5:

[0187] Intermediate 1-1 (10 mmol), compound 5-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M5 with a molar weight of 8.87 mmol and a yield of 88.7%; the atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M5 was: MS (ASAP) = 696.

[0188] Example 6

[0189] The synthetic route of organic compound M6 is as follows:

[0190]

[0191] Synthesis of intermediate 6-3:

[0192] Intermediate 6-1 (10 mmol), compound 6-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 6-3, whose molar weight was 9.14 mmol and the yield was 91.4%; atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 6-3: MS (ASAP) = 403.

[0193] Synthesis of organic compound M6:

[0194] The intermediate 6-3 (10 mmol), compound 3-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M6 with a molar weight of 8.15 mmol and a yield of 81.5%; the atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M6 was: MS (ASAP) = 629.

[0195] Example 7

[0196] The synthetic route of organic compound M7 is as follows:

[0197]

[0198] Synthesis of organic compound M7:

[0199] The intermediate 6-3 (10 mmol), compound 4-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M7 with a molar weight of 8.59 mmol and a yield of 85.9%; the atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M7 was: MS (ASAP) = 629.

[0200] Example 8

[0201] The synthetic route of organic compound M8 is as follows:

[0202]

[0203] Synthesis of organic compound M8:

[0204] The intermediate 6-3 (10 mmol), compound 5-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M8 with a molar weight of 8.94 mmol and a yield of 89.4%; the atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M8 was: MS (ASAP) = 696.

[0205] Example 9

[0206] The synthetic route of organic compound M9 is as follows:

[0207]

[0208] Synthesis of organic compound M9:

[0209] The intermediate 6-3 (10 mmol), compound 2-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M9 with a molar weight of 8.27 mmol and a yield of 82.7%; the atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M9 was: MS (ASAP) = 696.

[0210] Example 10

[0211] The synthetic route of organic compound M10 is as follows:

[0212]

[0213] Synthesis of organic compound M10:

[0214] The intermediate 6-3 (10 mmol), compound 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M10 with a molar weight of 8.63 mmol and a yield of 86.3%; the atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M10 was: MS (ASAP) = 695.

[0215] Embodiment 11

[0216] The synthetic route of organic compound M11 is as follows:

[0217]

[0218] Synthesis of organic compound M11:

[0219] The intermediate 6-3 (10 mmol), compound 11-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M11 with a molar weight of 8.95 mmol and a yield of 89.5%; the atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M11 was: MS (ASAP) = 695.

[0220] Example 12

[0221] The synthetic route of organic compound M12 is as follows:

[0222]

[0223] Synthesis of organic compound M12:

[0224] Intermediate 1-1 (10 mmol), compound 12-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M11 with a molar weight of 8.32 mmol and a yield of 83.2%; the atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M11 was: MS (ASAP) = 695.

[0225] Example 13

[0226] The synthetic route of organic compound M13 is as follows:

[0227]

[0228] Synthesis of organic compound M13:

[0229] Intermediate 1-1 (10 mmol), compound 13-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M13 with a molar weight of 8.73 mmol and a yield of 87.3%; the atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M13 was: MS (ASAP) = 663.

[0230] Embodiment 14

[0231] The synthetic route of organic compound M14 is as follows:

[0232]

[0233] Synthesis of organic compound M14:

[0234] Intermediate 1-1 (10 mmol), compound 14-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M14 with a molar weight of 9.04 mmol and a yield of 90.4%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of compound M14 was: MS (ASAP) = 663.

[0235] Embodiment 15

[0236] The synthetic route of organic compound M15 is as follows:

[0237]

[0238] Synthesis of organic compound M15:

[0239] Intermediate 6-3 (10 mmol), compound 13-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M15 with a molar weight of 8.26 mmol and a yield of 82.6%; the atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M15 was: MS (ASAP) = 663.

[0240] (II) Determination of energy levels, extinction coefficients and refractive index of organic compounds

[0241] In the embodiments of the present application, the energy level of the organic compound can be obtained by quantum calculation, for example, using time-dependent density functional theory (TD-DFT) through Gaussian09W (Gaussian Inc.), and the specific simulation method can be found in WO2011141110. First, the molecular geometry is optimized using the semi-empirical method "Ground State / DFT / Default Spin / B3LYP / 6-31G(d)" (Charge 0 / Spin Singlet), and the energy structure of the organic molecule is calculated by the TD-DFT method "TD-SCF / DFT / Default Spin / B3PW91" and the basis set "6-31G(d)" (Charge 0 / Spin Singlet).

[0242] In an embodiment of the present application, an organic compound is deposited on single crystal silicon by vacuum evaporation to form a 50 nm thin film. The single crystal silicon is placed on the sample stage of an ellipsometer (ES-01), the incident angle is adjusted to 70°, the test environment is an atmospheric environment, and the extinction coefficient (k) and refractive index (n) test results of the organic compound are obtained by the ellipsometer.

[0243] The singlet (S1) energy level, extinction coefficient at a wavelength of 430 nanometers and refractive index at a wavelength of 630 nanometers of the organic compounds M1 to M15 and the comparative compound CBP provided in Examples 1 to 15 were measured by the above method, and the results are shown in Table 1.

[0244] Table 1

[0245]

[0246] It can be seen from Table 1 that the organic compounds M1 to M15 provided in Examples 1 to 15 of the present application have weak absorption in the visible light band and high absorption in the ultraviolet band, and can resist damage to the inside of the device by external high-energy light while ensuring a high visible light transmittance; and, compared with the comparative compound CBP, the organic compounds M1 to M15 provided in Examples 1 to 15 of the present application have a higher refractive index, and a higher refractive index can ensure a better light extraction effect.

[0247] (III) Preparation and characterization of OLED devices

[0248] The preparation process of the aforementioned OLED device is described in detail below through a specific device embodiment. The structure of the OLED device is: ITO / Ag / ITO (anode) / HATCN / SFNFB / m-CP:Ir(p-ppy)3 / NaTzF2 / LiF / Mg:Ag / light extraction layer.

[0249] The steps for preparing the OLED-1 device provided in Device Example 1 are as follows:

[0250] The ITO conductive glass anode layer was cleaned by ultrasonic cleaning with deionized water, acetone, and isopropanol for 15 minutes, and then treated in a plasma cleaner for 5 minutes to improve the electrode work function;

[0251] On the ITO anode layer, the hole injection layer material HATCN is evaporated by vacuum evaporation with a thickness of 5nm and an evaporation rate of obtaining a hole injection layer;

[0252] On the hole injection layer, a hole transport material SFNFB is deposited by vacuum evaporation to a thickness of 80 nm to obtain a hole transport layer;

[0253] A light-emitting layer was evaporated on the hole transport layer, with m-CP as the main material, Ir(p-ppy)3 as the doping material, the mass ratio of Ir(p-ppy)3 to m-CP being 1:9, and the thickness being 30 nm, to obtain a light-emitting layer;

[0254] On the light-emitting layer, electron transport material NaTzF2 is evaporated by vacuum evaporation with a thickness of 30 nm to obtain an electron transport layer;

[0255] On the electron transport layer, LiF, a material of the electron injection layer, is vacuum-deposited to a thickness of 1 nm to obtain an electron injection layer;

[0256] On the electron injection layer, a cathode Mg:Ag layer was vacuum-deposited, with a Mg:Ag doping ratio of 9:1 and a thickness of 15 nm, to obtain a cathode layer;

[0257] On the cathode layer, an organic compound M1 was deposited by vacuum deposition to form a light extraction layer with a thickness of 60 nm.

[0258] Device Examples 2 to 15 refer to the preparation method of Device Example 1, except that the organic compounds M2 to M15 in Table 1 are used as the light extraction layer materials of the OLED device, and OLED-2 to OLED-15 devices are prepared accordingly. It can be understood that in the preparation methods of devices OLED-1 to OLED-15, except for the different light extraction layer materials, the other experimental conditions are the same. Similarly, Device Comparative Example 1 refers to the preparation method of Device Example 1, except that the light extraction layer material is changed to CBP, and OLED-Ref is prepared accordingly.

[0259] The chemical structural formula of the compound involved in the preparation method of the OLED device is as follows:

[0260]

[0261] The present invention tests the luminous efficiency (CE, cd / A) of OLED-1 to OLED-15 and OLED-Ref devices. The luminous efficiency is measured at a current density of 10 mA / cm 2 The results are shown in Table 2.

[0262] Table 2

[0263] Devices Light extraction layer compound Luminous efficiency (cd / A) OLED-1 M1 120 OLED-2 M2 121 OLED-3 M3 113 OLED-4 M4 115 OLED-5 M5 116 OLED-6 M6 118 OLED-7 M7 117 OLED-8 M8 115 OLED-9 M9 115 OLED-10 M10 109 OLED-11 M11 113 OLED-12 M12 108 OLED-13 M13 112 OLED-14 M14 109 OLED-15 M15 110 OLED-Ref CBP 87

[0264] As can be seen from Table 2, compared with the comparative compound CBP, the organic compounds M1 to M15 provided in Examples 1 to 15 of the present application as light extraction layer materials can effectively improve the luminous efficiency of the OLED device. This is because compared with the light extraction layer material CBP in the comparative example light-emitting device (OLED-Ref), the organic compounds M1 to M15 provided in the embodiments of the present application add several large groups that are focused on protection in the present application, such as ortho-phenylnaphthobenzofuran groups, phenanthrophenyloxazole groups, diazadibenzothiophene or chrysene groups, and also add at least one phenylbenzooxazole group. The combination of these large groups effectively improves the refractive index of the light extraction layer and further improves the luminous efficiency of the OLED device.

[0265] Therefore, in the organic compounds, organic electronic devices and display panels of the embodiments of the present application, the organic compound shown in Formula 1 is a triarylamine organic compound, and the chemical structure of the organic compound includes at least one of large groups such as an ortho-phenylnaphthobenzofuran group, a phenanthrophenyloxazole group, a diazadibenzothiophene or a chrysene group. At the same time, the chemical structure of the organic compound also includes at least one phenylbenzoxazole group. The combination of these large groups enables the organic compound to have a higher glass transition temperature and thermal stability; and the organic compound contains multiple N atoms, which can enhance the electron-withdrawing ability of the group and improve the electron push-pull of the entire organic compound molecule, which is beneficial to regulating the energy level and dipole moment of the organic compound molecule, and further beneficial to improving the ultraviolet absorption and molecular refractive index of the organic compound molecule below a wavelength of 400 nm, so that the organic compound has a high extinction coefficient in the ultraviolet band, a small extinction coefficient in the visible light range, and a higher refractive index. Therefore, the organic compound can be used as a light extraction layer material in the light extraction layer of an organic electronic device, which can prevent harmful light from having an adverse effect on the materials inside the organic electronic device and can effectively improve the visible light extraction efficiency.

[0266] The above-mentioned embodiments only express several implementation methods of the present application, and the descriptions thereof are relatively specific and detailed, but they cannot be understood as limiting the scope of protection of the present application. It should be pointed out that, for ordinary technicians in this field, several variations and improvements can be made without departing from the inventive concept of the present application, and these all belong to the scope of protection of the present application.

Claims

1. An organic compound, characterized in that The chemical structural formula of the organic compound is shown in Formula 1: Wherein, Ar1 is selected from any one or a combination of the following groups: Y1, Y2, Y3, Y4, Y5, Y6, Y7 and Y8 are selected from N or CR4; X is selected from CR5R6, C=C(R5R6), SiR5R6, NR5, C(=O), S, SO2, S(=O) or O; Ar2 is selected from any one of the following groups: The dashed lines in Ar1 and Ar2 represent single bonds; L1 is selected from a single bond, an alkenyl group, an alkynyl group, an acyl group, an amide group, a carbonyl group, a sulfone group, a substituted or unsubstituted alkyl group having 1 to 60 C atoms, a substituted or unsubstituted alkoxy group having 1 to 60 C atoms, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms; R1, R2, R3, R4, R5 and R6 are selected from hydrogen, D, linear alkyl having 1 to 20 C atoms, linear alkoxy having 1 to 20 C atoms, linear thioalkoxy having 1 to 20 C atoms, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, branched or cyclic thioalkoxy having 3 to 20 C atoms, silyl, keto having 1 to 20 C atoms, alkoxycarbonyl having 2 to 20 C atoms, aryloxycarbonyl having 7 to 20 C atoms, cyano, At least one of carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, an aryloxy group having 5 to 60 ring atoms, and a heteroaryloxy group having 5 to 60 ring atoms; among the R1, R2, R3, R4, R5 and R6 groups, two or more adjacent groups can form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system.

2. The organic compound according to claim 1, characterized in that The Ar2 is selected from any one of the following groups:

3. The organic compound according to claim 2, characterized in that The organic compound is selected from any one of the compounds represented by Formula 2-1 to Formula 2-9:

4. The organic compound according to claim 1 or 3, characterized in that The Ar1 is selected from any one or a combination of the following groups: wherein the H atoms on the ring of the Ar1 group are not substituted or are substituted by R7; R7 is selected from D, linear alkyl having 1 to 20 C atoms, linear alkoxy having 1 to 20 C atoms, linear thioalkoxy having 1 to 20 C atoms, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, branched or cyclic thioalkoxy having 3 to 20 C atoms, silyl, keto having 1 to 20 C atoms, alkoxycarbonyl having 2 to 20 C atoms, aryloxycarbonyl having 7 to 20 C atoms, cyano , carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, an aryloxy group having 5 to 60 ring atoms, and a heteroaryloxy group having 5 to 60 ring atoms; two or more adjacent R7 groups can form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system.

5. The organic compound according to claim 1 or 3, characterized in that The L1 is selected from a single bond or at least one of the following groups: Wherein, W is selected from N or CR8; R8 is selected from hydrogen, D, linear alkyl having 1 to 20 C atoms, linear alkoxy having 1 to 20 C atoms, linear thioalkoxy having 1 to 20 C atoms, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, branched or cyclic thioalkoxy having 3 to 20 C atoms, silyl, keto having 1 to 20 C atoms, alkoxycarbonyl having 2 to 20 C atoms, aryloxycarbonyl having 7 to 20 C atoms, cyano R8 is a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, an aryloxy group having 5 to 60 ring atoms, or a heteroaryloxy group having 5 to 60 ring atoms; two or more adjacent R8 groups may form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system; X1 is selected from CR5R6, C=C(R5R6), SiR5R6, NR5, C(=O), S, SO2, S(=O) or O.

6. The organic compound according to claim 5, characterized in that The organic compound is selected from any one of the compounds represented by Formula 3-1 to Formula 3-9:

7. The organic compound according to claim 1, characterized in that The refractive index of the organic compound for light with a wavelength of 630 nm is greater than 1.7, and the extinction coefficient of the organic compound for light with a wavelength of 430 nm is less than 0.

1.

8. The organic compound according to claim 1, characterized in that The singlet energy of the organic compound is greater than or equal to 2.7 eV.

9. An organic electronic device, characterized in that: include: a first electrode; a second electrode, arranged opposite to the first electrode; an organic functional layer, located between the first electrode and the second electrode; The light extraction layer is located on the side of the first electrode away from the organic functional layer, or on the side of the second electrode away from the organic functional layer. The material of the light extraction layer includes at least one of the organic compounds described in any one of claims 1 to 8.

10. A display panel, characterized in that: The organic electronic device according to claim 9.

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