Organic compound, composition, and organic electronic device

Abstract

The invention relates to an organic compound, a composition and an organic electronic device. The organic compound has a structural formula as shown in formula (1): # imgabs0 # (1); large groups, such as naphthyl benzothiazole, naphthyl phenyl benzothiazole group and at least one phenyl benzoxazole or phenyl benzothiazole group, are added into the organic compound, so that the glass transition temperature of the organic compound is increased, the thermal stability of the organic compound is improved, and the organic compound has a good application prospect. The extinction coefficient of the organic compound in an ultraviolet band is high, the extinction coefficient of the organic compound in a visible light range is small, and the organic compound has a high refractive index; when the organic compound provided by the invention is used as a light extraction layer material of an organic electronic device, adverse effects of harmful light on internal materials of the device can be avoided, and the light extraction efficiency of visible light can be improved.

Description

Technical Field

[0001] The present application relates to the technical field of organic electroluminescence, and in particular to an organic compound, a composition and an organic electronic device. 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] In recent years, 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, the matching of the refractive index between the functional layers, etc.). In 2001, Hung et al. covered the surface of the metal cathode with a layer of about 50nm of organic or inorganic compounds, 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 use organic compounds with a higher refractive index in electroluminescent devices to improve the light extraction efficiency. Such compounds must meet the following conditions: high extinction coefficient in the ultraviolet band (<400nm) to avoid the adverse effects of harmful light on device materials; extinction coefficient close to 0 in the visible light range (>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, a composition and an organic electronic device, which are used in a light extraction layer of an organic electronic device to improve the light extraction efficiency of the organic electronic device.

[0007] In order to achieve the above-mentioned object, an embodiment of the present application provides an organic compound, wherein the organic compound has a structural formula as shown in formula (1): (1); Among them, Ar 1 At least one selected from the following groups: ; Y 1 ~Y 8 Each time it appears, it is independently selected from N, CR 4 , the dotted line represents Ar 1 With L 1 connected keys; X is selected from CR 5 R 6 , C=C(R 5 R 6 )、SiR 5 R 6 NR 5 、C(=O)、S、SO 2 , S(=O) or O; Ar 2 is selected from substituted or unsubstituted benzothiazolyl groups having 7 to 30 carbon atoms; L 1 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 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms; R 1 , R 2 , R 3 , R 4 , R 5 and R 6 Each occurrence is independently selected from hydrogen, D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched or cyclic alkyl group having 3 to 20 carbon atoms, a branched or cyclic alkoxy group having 3 to 20 carbon atoms, a branched or cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, a CF 3, 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, or a heteroaryloxy group having 5 to 60 ring atoms; R 1 , R 2 , R 3 , R 4 , R 5 and R 6 At least two adjacent groups in the group are not ring-forming, or form an aliphatic, aromatic or heteroaromatic ring system having at least one ring.

[0008] In one embodiment of the present application, Ar 1 At least one selected from the following groups: .

[0009] In one embodiment of the present application, Ar 1 At least one selected from the following groups: ; Where: Ar 1 The H atoms in the ring are unsubstituted or replaced by R 7 replace; R 7 Each occurrence is independently selected from D, a linear alkyl group having 1 to 20 carbon atoms, a linear alkoxy group having 1 to 20 carbon atoms, a linear thioalkoxy group having 1 to 20 carbon atoms, a branched or cyclic alkyl group having 3 to 20 carbon atoms, a branched or cyclic alkoxy group having 3 to 20 carbon atoms, a branched or cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, a CF 3 , 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; wherein at least two adjacent R 7 They are acyclic or form with each other an aliphatic, aromatic or heteroaromatic ring system having at least one ring.

[0010] In one embodiment of the present application, Ar 2 Selected from one of the following groups:

[0011]

[0012]

[0013] ; The dotted line represents Ar 2 The bond connected to N is a single bond.

[0014] In one embodiment of the present application, Ar 2 Selected from one of the following groups:

[0015]

[0016]

[0017] .

[0018] In one embodiment of the present application, X is selected from O or S. In one embodiment of the present application, L 1 Selected from a single bond or at least one of the following groups: ; Wherein, each occurrence of W is independently selected from N or CR 8 ; R 8 Each occurrence is independently selected from hydrogen, D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched or cyclic alkyl group having 3 to 20 carbon atoms, a branched or cyclic alkoxy group having 3 to 20 carbon atoms, a branched or cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, a CF 3 , 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, or a heteroaryloxy group having 5 to 60 ring atoms; at least two adjacent R 8 They are acyclic, or form with each other an aliphatic, aromatic or heteroaromatic ring system having at least one ring.

[0019] In one embodiment of the present application, the organic compound is selected from any one of the following formulas (2-1) to (2-16): .

[0020] In one embodiment of the present application, the organic compound is selected from any one of the following formulas (3-1) to (3-16): .

[0021] In one embodiment of the present application, the organic compound is selected from any one of the following formulas (4-1) to (4-16): .

[0022] According to the above-mentioned purpose of the present application, an embodiment of the present application further provides a composition, which includes at least one organic solvent and at least one organic compound.

[0023] According to the above-mentioned purpose of the present application, an embodiment of the present application further provides an organic electronic device, which includes: a first electrode; a second electrode, arranged opposite to the first electrode; An organic functional layer, disposed between the first electrode and the second electrode; The light extraction layer is arranged on the side of the second electrode away from the organic functional layer. The material of the light extraction layer includes the organic compound, or the material of the light extraction layer includes the composition.

[0024] The present application increases the glass transition temperature of the organic compound and the thermal stability of the organic compound by adding a large group, such as a naphthyl benzothiazole, a naphthylphenyl benzothiazole group, or at least one phenylbenzoxazole or phenylbenzothiazole group, to the organic compound, 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 high refractive index; when the organic compound provided by the present application is used as a light extraction layer material for an organic electronic device, it can avoid the adverse effects of harmful light on the internal materials of the device and improve the visible light extraction efficiency.

[0025] Other features and advantages of the present application will be described in detail in the subsequent detailed description. BRIEF DESCRIPTION OF THE DRAWINGS In order to more clearly illustrate the technical solutions in the embodiments of the present application, the following briefly introduces the drawings required for use in the description of the embodiments. Obviously, the drawings described below are only some embodiments of the present application, and those skilled in the art can obtain other drawings based on these drawings without creative work.

[0026] 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.

[0027] Figure 1 A schematic diagram of the structure of an organic electronic device provided in an embodiment of the present application; Figure 2 Another schematic diagram of the structure of an organic electronic device provided in an embodiment of the present application; Figure 3 This is the NMR spectrum of the organic compound M1 provided in the examples of the present application.

[0028] Description of reference numerals: 100. Organic electronic device; 11. First electrode; 12. Second electrode; 20. Organic functional layer; 21. Hole injection layer; 22. Hole transport layer; 23. Light-emitting layer; 24. Electron transport layer; 25. Electron injection layer; 30. Light extraction layer; 40. Substrate. DETAILED DESCRIPTION

[0029] 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.

[0030] In the present application, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0031] In the present application, the "number of ring atoms" refers to the number of 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) in which atoms are bonded 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.

[0032] 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".

[0033] Aromatic groups refer to hydrocarbon groups containing at least one aromatic ring. Heteroaromatic groups refer to aromatic hydrocarbon groups 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. Condensed ring aromatic groups refer to aromatic groups whose rings may have two or more rings, wherein two carbon atoms are shared by two adjacent rings, i.e., condensed rings. Condensed heterocyclic aromatic groups refer to condensed ring aromatic hydrocarbon groups containing at least one heteroatom. For the purposes of this application, aromatic groups or heteroaromatic groups include not only systems of aromatic rings, but also non-aromatic ring systems. 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 this purpose. For the purposes of this application, 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 (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 this purpose.

[0034] The present invention provides an organic compound having a structural formula as shown in formula (1): (1); Among them, Ar 1 At least one selected from the following groups: ; Y 1 ~Y 8 Each time it appears, it is independently selected from N, CR 4 , the dotted line represents Ar 1 With L 1 connected keys; X is selected from CR 5 R6 , C=C(R 5 R 6 )、SiR 5 R 6 NR 5 、C(=O)、S、SO 2 , S(=O) or O; Ar 2 is selected from substituted or unsubstituted benzothiazolyl groups having 7 to 30 carbon atoms; L 1 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 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms; R 1 , R 2 , R 3 , R 4 , R 5 and R 6 Each occurrence is independently selected from hydrogen, D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched or cyclic alkyl group having 3 to 20 carbon atoms, a branched or cyclic alkoxy group having 3 to 20 carbon atoms, a branched or cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, a CF 3 , 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, or a heteroaryloxy group having 5 to 60 ring atoms; R 1 , R 2 , R 3 , R 4 , R 5 and R 6 At least two adjacent groups in the group are not ring-forming, or form an aliphatic, aromatic or heteroaromatic ring system having at least one ring.

[0035] In the implementation and application process, the present application increases the glass transition temperature of the organic compound and the thermal stability of the organic compound by adding large groups, such as naphthyl benzothiazole, naphthylphenyl benzothiazole groups, and at least one phenylbenzoxazole or phenylbenzothiazole group, to the organic compound, 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 high refractive index; when the organic compound provided by the present application is used as a light extraction layer material for an organic electronic device, it can avoid the adverse effects of harmful light on the internal materials of the device and improve the visible light extraction efficiency.

[0036] Specifically, in some embodiments, Y 1 ~Y 4 At least one of them is N.

[0037] In a preferred embodiment, Ar 1 Y 1 ~Y 4 Middle Y 1 or Y 4 is N; more preferably, Y 1 ~Y 4 At least two of them are N; most preferably, Y 1 and Y 4 At the same time it is N.

[0038] In a preferred embodiment, Ar 1 Y 5 ~Y 8 At least one of them is N; more preferably, Y 5 ~Y 8 At least two of them are N; most preferably, Y 5 and Y 8 At the same time it is N.

[0039] Because Y 1 ~Y 8 The number of N atoms in the group affects the electron-withdrawing ability of the group. N atoms can enhance the electron-withdrawing ability of the group, improve the electron push and pull of the entire molecule, regulate the energy level and dipole moment of the molecule, and increase the ultraviolet absorption of the molecule below 400nm wavelength and the refractive index of the molecule.

[0040] In some embodiments, Ar 1 At least one selected from the following groups: .

[0041] More preferably, Ar 1 At least one selected from the following groups: .

[0042] In some embodiments, the present invention relates to Y 1 To Y 4 Make a selection, and Ar 1 At least one selected from the following groups: .

[0043] Among them, Ar 1 The H atoms in the ring are unsubstituted or replaced by R 7 replace; R 7 Each occurrence is independently selected from D, a linear alkyl group having 1 to 20 carbon atoms, a linear alkoxy group having 1 to 20 carbon atoms, a linear thioalkoxy group having 1 to 20 carbon atoms, a branched or cyclic alkyl group having 3 to 20 carbon atoms, a branched or cyclic alkoxy group having 3 to 20 carbon atoms, a branched or cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, a CF 3 , 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; wherein at least two adjacent R 7 They are acyclic or form with each other an aliphatic, aromatic or heteroaromatic ring system having at least one ring.

[0044] In some embodiments, Ar 1 The H atoms in the ring are not substituted.

[0045] Further, in some embodiments, Ar 1 At least one selected from the following groups: .

[0046] More preferably, Ar 1 At least one selected from the following groups: .

[0047] In some embodiments, Ar 2 One selected from the following groups:

[0048]

[0049]

[0050] .

[0051] The dotted line represents Ar 2 The bond connected to N is a single bond, Ar 2 Any carbon atom can be attached to a nitrogen atom.

[0052] In some embodiments, Ar 2 Selected from one of the following groups:

[0053]

[0054]

[0055] .

[0056] More preferably, Ar 2 Selected from one of the following groups:

[0057] .

[0058] In some embodiments, X is selected from O or S. In some embodiments, L 1 Selected from a single bond or at least one of the following groups: ; Wherein, each occurrence of W is independently selected from N or CR 8 .

[0059] R 8 Each occurrence is independently selected from hydrogen, D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched or cyclic alkyl group having 3 to 20 carbon atoms, a branched or cyclic alkoxy group having 3 to 20 carbon atoms, a branched or cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, a CF 3, 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, or a heteroaryloxy group having 5 to 60 ring atoms; at least two adjacent R 8 They are acyclic, or form with each other an aliphatic, aromatic or heteroaromatic ring system having at least one ring.

[0060] In some embodiments, L 1 Selected from a single bond or one or a combination of the following groups:

[0061]

[0062]

[0063]

[0064] .

[0065] The H atoms on the ring may be further substituted.

[0066] Furthermore, L 1 One or a combination of the following groups: .

[0067] The H atoms on the ring may be further substituted.

[0068] More preferably, L 1 Selected from .

[0069] In some embodiments, the organic compound is selected from any one of the following formulas (2-1) to (2-16): .

[0070] Furthermore, in the present embodiment, L 1 The organic compound is selected from any one of the following formulas (3-1) to (3-16): .

[0071] Furthermore, in some embodiments, the organic compound is selected from any one of the following formulas (4-1) to (4-16): .

[0072] In some embodiments, Y 1 -Y 4 All are CH.

[0073] In some embodiments, the structural formula of the organic compound provided in the embodiments of the present application is selected from one of the following compounds:

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088] .

[0089] It should be noted that, in the above-listed examples of organic compounds of the present application, H in the structural formula may be further substituted arbitrarily, for example, by deuterium.

[0090] The organic compound provided in the embodiments of the present application has a relatively high glass transition temperature, which can improve the thermal stability of the compound.

[0091] In some embodiments, the glass transition temperature of the organic compound is g Greater than or equal to 100°C. In a preferred embodiment, T g Greater than or equal to 120°C. In a preferred embodiment, T g Greater than or equal to 140°C. In a more preferred embodiment, T g Greater than or equal to 160°C. In a most preferred embodiment, T g Greater than or equal to 180°C.

[0092] In some embodiments, the refractive index of the organic compound provided in the embodiments of the present application at a wavelength of 630 nm is greater than 1.7; preferably, the refractive index of the organic compound at a wavelength of 630 nm is greater than 1.78; more preferably, the refractive index of the organic compound at a wavelength of 630 nm is greater than 1.83.

[0093] In some embodiments, the singlet energy (S1) of the organic compound provided in the embodiments of the present application is greater than or equal to 2.7 eV; preferably, the singlet energy (S1) of the organic compound is greater than or equal to 2.8 eV; more preferably, the singlet energy (S1) of the organic compound is greater than or equal to 2.85 eV.

[0094] The organic compound provided in the embodiment of the present application has a small extinction coefficient, and the extinction coefficient of the organic compound at a wavelength of 430 nm is less than 0.1; preferably, the extinction coefficient of the organic compound at a wavelength of 430 nm is less than 0.003; more preferably, the extinction coefficient of the organic compound at a wavelength of 430 nm is less than 0.001.

[0095] The organic compound provided in the embodiment of the present application has a high transmittance to visible light, reducing the impact on the light extraction efficiency of the device.

[0096] In some embodiments, the organic compound provided in the embodiments of the present application has a larger extinction coefficient in a wavelength range less than or equal to 400 nm; preferably, the extinction coefficient of the organic compound at a wavelength of 350 nm is greater than or equal to 0.3; the extinction coefficient of the organic compound at a wavelength of 350 nm is preferably greater than or equal to 0.5, the extinction coefficient of the organic compound at a wavelength of 350 nm is more preferably greater than or equal to 0.7, and the extinction coefficient of the organic compound at a wavelength of 350 nm is preferably greater than or equal to 1.0.

[0097] The organic compound provided in the embodiment of the present application can be used for the preparation of vapor deposition type OLED.

[0098] In some embodiments, the molecular weight of the organic compound provided in the embodiments of the present application is less than or equal to 1200 g / mol, the molecular weight of the organic compound provided in the embodiments of the present application is preferably less than or equal to 1100 g / mol, the molecular weight of the organic compound provided in the embodiments of the present application is further preferably less than or equal to 1000 g / mol, the molecular weight of the organic compound provided in the embodiments of the present application is more preferably less than or equal to 950 g / mol, and the molecular weight of the organic compound provided in the embodiments of the present application is most preferably less than or equal to 900 g / mol.

[0099] The organic compound provided in the embodiment of the present application can be used for the preparation of printed OLED.

[0100] In some embodiments, the molecular weight of the organic compound provided in the embodiments of the present application is greater than or equal to 800 g / mol, the molecular weight of the organic compound provided in the embodiments of the present application is preferably greater than or equal to 900 g / mol, the molecular weight of the organic compound provided in the embodiments of the present application is further preferably greater than or equal to 1000 g / mol, the molecular weight of the organic compound provided in the embodiments of the present application is more preferably greater than or equal to 1100 g / mol, and the molecular weight of the organic compound provided in the embodiments of the present application is most preferably greater than or equal to 1200 g / mol.

[0101] In other embodiments, the molecular weight of the organic compound provided in the embodiments of the present application has a solubility in toluene at 25°C greater than or equal to 2 mg / ml, preferably greater than or equal to 3 mg / ml, more preferably greater than or equal to 4 mg / ml, and most preferably greater than or equal to 5 mg / ml.

[0102] Continuing from the above, the present application increases the glass transition temperature of the organic compound and the thermal stability of the organic compound by adding a large group, such as a naphthyl benzothiazole, a naphthylphenyl benzothiazole group, or at least one phenylbenzoxazole or phenylbenzothiazole group, to the organic compound, 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 high refractive index; when the organic compound provided by the present application is used as a light extraction layer material of an organic electronic device, it can avoid the adverse effects of harmful light on the internal materials of the device and improve the visible light extraction efficiency.

[0103] According to the above-mentioned purpose of the present application, an embodiment of the present application further provides a composition, which includes at least one organic solvent and at least one organic compound.

[0104] In some embodiments, the organic solvent is selected from aromatic or heteroaromatic compounds, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, alicyclic or olefinic compounds, or borate or phosphate compounds, or a mixture of two or more solvents.

[0105] 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.

[0106] Examples of the 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-methylphenyl Acetone, 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 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: octanoic acid alkyl esters, sebacate alkyl esters, stearic acid alkyl esters, benzoic acid alkyl esters, phenylacetic acid alkyl esters, cinnamic acid alkyl esters, oxalic acid alkyl esters, maleic acid alkyl esters, alkanolides, oleic acid alkyl esters, etc.

[0107] Further, 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.

[0108] In other embodiments, the organic solvent may also include (but is 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.

[0109] In a preferred embodiment, the composition provided in the examples of the present application is a solution.

[0110] In another preferred embodiment, the composition provided in the examples of the present application is a suspension.

[0111] In the composition provided in the embodiments of the present application, the proportion of the organic compound in the composition can range from 0.01 to 20wt%, preferably 0.1 to 15wt%, more preferably 0.2 to 10wt%, and most preferably 0.25 to 5wt% of the organic compound.

[0112] The composition provided in the embodiments of the present application can also be used as a coating or printing ink to prepare organic electronic devices, and a preparation method by printing or coating is particularly preferred.

[0113] Among them, suitable printing or coating techniques include (but are not limited to) inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, twist roller printing, lithography, flexographic printing, rotary printing, spraying, brushing or 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 detailed information on printing technology and its related requirements for related solutions, such as solvents and concentrations, viscosity, etc., please refer to the "Handbook of Print Media: Technologies and Production Methods" edited by Helmut Kipphan, ISBN3-540-67326-1.

[0114] In addition, please refer to Figure 1 The embodiment of the present application further provides an organic electronic device 100, wherein the organic electronic device 100 comprises at least one compound as described above.

[0115] In some embodiments, the organic electronic device 100 may include an organic light emitting diode, an organic photovoltaic cell, an organic light emitting cell, an organic field effect transistor, an organic light emitting field effect transistor, an organic laser, an organic spin electronic device, an organic sensor, and an organic plasmon emission diode, etc., with an organic light emitting diode being particularly preferred.

[0116] Preferably, the compound provided in the embodiment of the present application can be used as an electron transport layer material, a light-emitting layer main material or a light extraction layer material of an organic electronic device.

[0117] Furthermore, the organic electronic device 100 provided in the embodiment of the present application includes a first electrode 11 , a second electrode 12 , an organic functional layer 20 and a light extraction layer 30 .

[0118] In some embodiments, the first electrode 11 and the second electrode 12 are disposed opposite to each other, the organic functional layer 20 is disposed between the first electrode 11 and the second electrode 12 , and the light extraction layer 30 is disposed on a side of the second electrode 12 away from the organic functional layer 20 .

[0119] In some embodiments, the material of the light extraction layer 30 includes the organic compound represented by formula (1) as described in the above embodiments, or the composition.

[0120] In some embodiments, the organic electronic device 100 may be an organic light-emitting diode device, and the first electrode 11 may be an anode, the second electrode 12 may be a cathode, the organic functional layer 20 may include at least one light-emitting layer 23; and the light extraction layer 30 is arranged on the surface of the cathode away from the light-emitting layer 23, or the light extraction layer 30 may also be arranged on the surface of the anode away from the light-emitting layer 23.

[0121] In some embodiments, the material of the light extraction layer 30 includes at least one of the compounds represented by formulas (2-1) to (2-16) in the above embodiments; preferably, the material of the light extraction layer 30 includes at least one of the compounds represented by formulas (3-1) to (3-16) in the above embodiments; more preferably, the material of the light extraction layer 30 includes at least one of the compounds represented by formulas (4-1) to (4-16) in the above embodiments.

[0122] In some embodiments, the organic compound in the material of the light extraction layer 30 has a relatively high glass transition temperature, which can improve the thermal stability of the organic compound. In some preferred embodiments, the glass transition temperature T g Greater than or equal to 100°C. In a preferred embodiment, T g Greater than or equal to 120°C. In a preferred embodiment, T g Greater than or equal to 140°C. In a more preferred embodiment, T g Greater than or equal to 160°C. In a most preferred embodiment, T g Greater than or equal to 180°C.

[0123] Since the organic compound in the material of the light extraction layer 30 has a higher refractive index, the light extraction layer 30 has a higher refractive index, which can help improve the light efficiency of the organic electronic device 100, especially help improve the external light emitting efficiency. For example, the refractive index of the light extraction layer 30 at a wavelength of 630nm is greater than or equal to 1.7; preferably, the refractive index of the light extraction layer 30 at a wavelength of 630nm is greater than or equal to 1.78; more preferably, the refractive index of the light extraction layer 30 at a wavelength of 630nm is greater than or equal to 1.83.

[0124] In some embodiments, the singlet energy (S1) contained in the light extraction layer 30 is greater than or equal to 2.7 eV; preferably, the singlet energy (S1) contained in the light extraction layer 30 is greater than or equal to 2.8 eV; more preferably, the singlet energy (S1) contained in the light extraction layer 30 is greater than or equal to 2.85 eV.

[0125] In other embodiments, the singlet energy (S1) contained in the light extraction layer 30 is less than or equal to 3.1 eV; preferably, the singlet energy (S1) contained in the light extraction layer 30 is less than or equal to 3.0 eV.

[0126] In some embodiments, the organic compound in the material of the light extraction layer 30 has a small extinction coefficient, and the extinction coefficient at a wavelength of 430 nm is less than 0.1; preferably, less than 0.003; more preferably, less than 0.001. The organic compound in the material of the light extraction layer 30 has a high transmittance to visible light, reducing the impact on the light extraction efficiency of the device.

[0127] In some embodiments, please refer to Figure 2 The organic electronic device 100 is an electroluminescent device, and the organic electronic device also includes a substrate 40. The first electrode 11 is arranged on the substrate 40, the organic functional layer 20 is arranged on the side of the first electrode 11 away from the substrate 40, the second electrode 12 is arranged on the side of the organic functional layer 20 away from the first electrode 11, and the light extraction layer 30 is arranged on the side of the second electrode 12 away from the organic functional layer 20.

[0128] In some embodiments, the organic functional layer 20 includes a hole injection layer 21, a hole transport layer 22, a light-emitting layer 23, an electron transport layer 24 and an electron injection layer 25, which are sequentially arranged on the side of the first electrode 11 away from the substrate 40, and the number of the light-emitting layer 23 can be at least one layer.

[0129] The organic electronic device 100 is preferably selected from an organic light emitting diode (OLED), an organic light emitting cell (OLEEC), an organic field effect transistor (OFET), and an organic light emitting field effect transistor.

[0130] The following is a detailed description of each film layer structure in the organic electronic device 100 .

[0131] In some embodiments, the first electrode 11 may include a conductive metal, a metal oxide, or a conductive polymer. The first electrode 11 may easily inject holes into the hole injection layer 21 (HIL), the hole transport layer 22, or the light emitting layer 23. In one embodiment, the absolute value of the difference between the work function of the first electrode 11 and the HOMO energy level or valence band energy level of the light emitter in the light emitting layer 23 or the p-type semiconductor material as the hole injection layer 21, the hole transport layer 22, 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. The material of the first electrode 11 includes, but is not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), etc. Other suitable materials for the first electrode 11 are known, and those skilled in the art can easily select and use them. The material of the first electrode 11 can be deposited using any suitable technique, such as a suitable physical vapor deposition method, specifically radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc. In some embodiments, the first electrode 11 is patterned. For example, patterned ITO conductive substrates are commercially available and can be used to prepare the organic electronic device 100 according to the embodiments of the present application.

[0132] In some embodiments, the second electrode 12 may include a conductive metal or a metal oxide. The second electrode 12 can easily inject electrons into the electron injection layer 25, the electron transport layer 24 or directly into the light-emitting layer 23. In one embodiment, the absolute value of the difference between the work function of the second electrode 12 and the LUMO energy level or conduction band energy level of the light-emitting body in the light-emitting layer 23 or the n-type semiconductor material serving as the electron injection layer 25, the electron transport layer 24 or the hole blocking layer 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 materials for the second electrode 12 in the embodiments of the present application. The materials of the second electrode 12 include, but are not limited to: Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF 2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The material of the second electrode 12 can be deposited using any suitable technique, such as a suitable physical vapor deposition method, specifically radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.

[0133] In some embodiments, the light extraction layer 30 has strong absorption in the region with a wavelength less than 400nm, and the light extraction layer 30 has weak or close to zero absorption in the visible light range with a wavelength greater than 400nm, thereby preventing the material inside the organic electronic device 100 from being damaged by high-energy light in the subsequent process. At the same time, the light extraction layer 30 has a higher refractive index, which can be used to beneficially guide the emission of visible light and improve the luminous efficiency of the organic electronic device 100. When the reflectivity of the interface between the light extraction layer 30 and the adjacent electrode is large, the influence of light interference is large. Therefore, the refractive index of the material constituting the light extraction layer 30 is preferably greater than the refractive index of the adjacent electrode. For example, the refractive index of the light extraction layer 30 is generally greater than 1.50 at 630nm, and the refractive index of the light extraction layer 30 is more preferably greater than 1.70 at 630nm, and the refractive index of the light extraction layer 30 is particularly preferably greater than 1.80 at 630nm.

[0134] In some embodiments, the thickness of the light extraction layer 30 ranges from 10 nm to 200 nm, preferably from 20 nm to 150 nm, more preferably from 30 nm to 100 nm, and most preferably from 40 nm to 90 nm.

[0135] The embodiments of the present application also relate to applications of the organic electronic device 100 in various electronic devices, such as display devices, lighting devices, light sources, sensors, and the like.

[0136] The preparation process of the organic compound provided in the embodiments of the present application will be described below in conjunction with preferred embodiments, but the embodiments of the present application are not limited to the following embodiments. It should be understood that the attached claims summarize the scope of the embodiments of the present application. Under the guidance of the concept of the present application, technicians in this field should realize that certain changes made to the embodiments of the present application will be covered by the spirit and scope of the claims of the present application. Specific embodiments 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.

[0138] Synthesis of organic compound M1:

[0139] Synthesis of organic compound M1: Intermediate 1-1 (10 mmol), compound 1-2 (10 mmol), Pd 2 (dba) 3(0.1mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h under nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution 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 9.15mmol and a yield of 91.5%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M1 was: MS (ASAP) = 662. And the NMR spectrum of the organic compound M1 is as follows Figure 3 shown.

[0140] Synthesis of organic compound M2:

[0141] Synthesis of organic compound M2: Intermediate 1-1 (10 mmol), compound 2-1 (10 mmol), Pd 2 (dba) 3 (0.1mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h under nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution 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 8.33mmol and a yield of 83.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M2 was: MS (ASAP) = 662.

[0142] Synthesis of organic compound M3:

[0143] Synthesis of organic compound M3: Intermediate 1-1 (10 mmol), compound 3-1 (10 mmol), Pd 2 (dba) 3 (0.1mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h under nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution 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 8.15mmol and a yield of 81.5%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M3 was: MS (ASAP) = 738.

[0144] Synthesis of organic compound M4:

[0145] Synthesis of organic compound M4: Intermediate 1-1 (10 mmol), compound 4-1 (10 mmol), Pd 2 (dba) 3 (0.1mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h under nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution 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 8.07mmol and a yield of 80.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M4 was: MS (ASAP) = 738.

[0146] Synthesis of organic compound M5:

[0147] Synthesis of organic compound M5: Intermediate 1-1 (10 mmol), compound 5-1 (10 mmol), Pd 2 (dba) 3 (0.1mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h under nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution 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 8.57mmol and a yield of 85.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M5 was: MS (ASAP) = 738.

[0148] Synthesis of organic compound M6:

[0149] Synthesis of intermediate 6-3: Intermediate 6-1 (10 mmol), compound 6-2 (10 mmol), Pd 2 (dba) 3(0.1mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h under nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain the intermediate 6-3 with a molar weight of 9.14mmol and a yield of 91.4%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the intermediate 6-3 was: MS (ASAP) = 403.

[0150] Synthesis of organic compound M6: Intermediate 6-3 (10 mmol), compound 6-4 (10 mmol), Pd 2 (dba) 3 (0.1mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h under nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution 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 8.32mmol and a yield of 83.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M6 was: MS (ASAP) = 738.

[0151] Synthesis of organic compound M7:

[0152] Synthesis of organic compound M7: Intermediate 6-3 (10 mmol), compound 7-1 (10 mmol), Pd 2 (dba) 3 (0.1mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h under nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution 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 9.05mmol and a yield of 90.5%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M7 was: MS (ASAP) = 738.

[0153] Synthesis of organic compound M8:

[0154] Synthesis of intermediate 8-3: Intermediate 8-1 (10 mmol), compound 8-2 (10 mmol), Pd 2 (dba) 3 (0.1mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h under nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain the intermediate 8-3 with a molar weight of 7.49mmol and a yield of 74.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the intermediate 8-3 was: MS (ASAP) = 403.

[0155] Synthesis of organic compound M8: Intermediate 8-3 (10 mmol), compound 6-4 (10 mmol), Pd 2 (dba) 3 (0.1mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h under nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution 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 8.15mmol and a yield of 81.5%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M8 was: MS (ASAP) = 738.

[0156] Synthesis of organic compound M9:

[0157] Synthesis of organic compound M9: Intermediate 9-1 (10 mmol), compound 1-2 (10 mmol), Pd 2 (dba) 3 (0.1mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h under nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution 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 8.54mmol and a yield of 85.4%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M9 was: MS (ASAP) = 694.

[0158] Synthesis of organic compound M10:

[0159] Synthesis of organic compound M10: Intermediate 9-1 (10 mmol), compound 2-1 (10 mmol), Pd 2 (dba) 3 (0.1mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h under nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution 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 9.15mmol and a yield of 91.5%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M10 was: MS (ASAP) = 694.

[0160] Synthesis of organic compound M11:

[0161] Synthesis of organic compound M11: Intermediate 9-1 (10 mmol), compound 3-1 (10 mmol), Pd 2 (dba) 3 (0.1mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h under nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution 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 7.68mmol and a yield of 76.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M11 was: MS (ASAP) = 770.

[0162] Synthesis of organic compound M12:

[0163] Synthesis of organic compound M12: Intermediate 9-1 (10 mmol), compound 4-1 (10 mmol), Pd 2 (dba) 3(0.1mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h under nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution 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 7.22mmol and a yield of 72.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M12 was: MS (ASAP) = 770.

[0164] Synthesis of organic compound M13:

[0165] Synthesis of organic compound M13: Intermediate 9-1 (10 mmol), compound 13-1 (10 mmol), Pd 2 (dba) 3 (0.1mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h under nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain compound M9 with a molar weight of 8.29mmol and a yield of 82.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M13 was: MS (ASAP) = 678.

[0166] Energy structure of organic compounds: The energy levels of organic compounds can be obtained by quantum calculation, for example, using TD-DFT (time-dependent density functional theory) through Gaussian09W (Gaussian Inc.), and the specific simulation method can be found in WO2011141110. First, the semi-empirical method "Ground State / DFT / Default Spin / B3LYP / 6-31G (d)" (Charge0 / Spin Singlet) is used to optimize the molecular geometry, and the energy structure of the organic molecule is calculated by the TD-DFT (time-dependent density functional theory) method "TD-SCF / DFT / Default Spin / B3PW91" and the basis set "6-31G (d)" (Charge0 / Spin Singlet).

[0167] The compound was deposited on single crystal silicon by vacuum evaporation to form a 50 nm thin film. The single crystal silicon was placed on the sample stage of an ellipsometer (ES-01) with an incident angle of 70°. The test was conducted in an atmospheric environment. The extinction coefficient (k) and refractive index (n) test results of the compound were obtained by the ellipsometer, and the data are shown in Table 1.

[0168] Table 1

[0169] As can be seen from Table 1 above, the organic compound provided in the embodiment of the present application has weak absorption in the visible light band and high absorption in the ultraviolet band, and can resist damage to the internal device by external high-energy light. Compared with the compound CBP in the comparative example, it has a higher refractive index, and the higher refractive index can ensure that the obtained light extraction layer 30 has a better light extraction effect.

[0170] Furthermore, in the organic compound provided in the embodiment of the present application, the three substituents connected to N all contain phenylbenzoxazole and phenyl (naphthyl) benzothiazole, which can enhance the refractive index, and the raw materials are easy to obtain and purify.

[0171] Preparation and characterization of OLED devices: The following is a detailed description of the specific embodiments. Figure 2 The preparation process of the organic electronic device 100 shown in the figure has a structure of: ITO / Ag / ITO (first electrode 11) / HATCN (hole injection layer 21) / SFNFB (hole transport layer 22) / m-CP:Ir (p-ppy) 3 (Light-emitting layer 23) / NaTzF 2 (Electron transport layer 24) / LiF (Electron injection layer 25) / Mg:Ag (Second electrode 12) / Light extraction layer 30, the preparation steps are as follows: Device Example 1: Clean the ITO conductive glass anode layer (first electrode 11), then ultrasonically clean it with deionized water, acetone, and isopropanol for 15 minutes, and then treat it in a plasma cleaner for 5 minutes to improve the electrode work function. 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 1Å / s. On the hole injection layer 21, the hole transport material SFNFB is evaporated by vacuum evaporation with a thickness of 80nm. Evaporate the light-emitting layer 23 on the hole transport layer 22, with m-CP as the main material and Ir (p-ppy) 3 As doping material, Ir (p-ppy) 3 The mass ratio of m-CP is 1:9, and the thickness is 30nm. On the light-emitting layer 23, the electron transport material NaTzF is evaporated by vacuum evaporation. 2, with a thickness of 30nm. On the electron transport layer 24, the electron injection layer LiF is vacuum evaporated with a thickness of 1nm, which is the electron injection layer 25. On the electron injection layer 25, the cathode Mg:Ag layer (second electrode 12) is vacuum evaporated, with a Mg:Ag doping ratio of 9:1 and a thickness of 15nm. On the second electrode 12, the organic compound M1 is vacuum evaporated to obtain the light extraction layer 30 with a thickness of 60nm.

[0172] Device Example 2: The organic compound in the light extraction layer 30 of the organic electronic device 100 is changed to M2.

[0173] Device Example 3: The organic compound in the light extraction layer 30 of the organic electronic device 100 is changed to M3.

[0174] Device Example 4: The organic compound in the light extraction layer 30 of the organic electronic device 100 is changed to M4.

[0175] Device Example 5: The organic compound in the light extraction layer 30 of the organic electronic device 100 is changed to M5.

[0176] Device Example 6: The organic compound in the light extraction layer 30 of the organic electronic device 100 is changed to M6.

[0177] Device Example 7: The organic compound in the light extraction layer 30 of the organic electronic device 100 is changed to M7.

[0178] Device Example 8: The organic compound in the light extraction layer 30 of the organic electronic device 100 is changed to M8.

[0179] Device Example 9: The organic compound in the light extraction layer 30 of the organic electronic device 100 is changed to M9.

[0180] Device Example 10: The organic compound in the light extraction layer 30 of the organic electronic device 100 is changed to M10.

[0181] Device Example 11: The organic compound in the light extraction layer 30 of the organic electronic device 100 is changed to M11.

[0182] Device Example 12: The organic compound in the light extraction layer 30 of the organic electronic device 100 is changed to M12.

[0183] Device Example 13: The organic compound in the light extraction layer 30 of the organic electronic device 100 is changed to M13.

[0184] Device Comparative Example 1: The organic compound in the light extraction layer 30 of the organic electronic device 100 is changed to CBP.

[0185] The structures of the compounds involved in the device are as follows: .

[0186] The luminous efficiency data of device embodiments 1 to 13 and device comparative example 1 are measured and shown in Table 2.

[0187] Table 2

[0188] Among them, the luminous efficiency in Table 2 is the current density of 10mA / cm 2 The data obtained when . It can be seen from Table 2 that compared with the device comparison example 1, the organic compound provided in the embodiment of the present application can effectively improve the luminous efficiency of the organic electronic device 100 when used as the light extraction layer 30. This is because compared with the organic compound CBP of the light extraction layer 30 in the device comparison example 1, the present application increases the glass transition temperature of the organic compound and the thermal stability of the organic compound by adding a large group, such as naphthyl benzothiazole, naphthylphenyl benzothiazole group, at least one phenylbenzoxazole or phenylbenzothiazole group, to the organic compound, 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; when the organic compound provided in the present application is used as the light extraction layer material of the organic electronic device 100, it can avoid the adverse effects of harmful light on the internal materials of the device and improve the visible light extraction efficiency.

[0189] In addition, an embodiment of the present application further provides a display panel, and the display panel includes the organic electronic device as described in the above embodiment.

[0190] It can be understood that, since the display panel has the same organic electronic device as in the above embodiment, the display panel has the same beneficial effects as the organic electronic device, which will not be described in detail herein.

[0191] In the description of this application, the terms "first" and "second" are used for descriptive purposes only and should not be understood as indicating or implying relative importance or implicitly indicating the number of technical features indicated. Thus, a feature defined as "first" or "second" may explicitly or implicitly include one or more features. In the description of this application, the meaning of "plurality" is two or more, unless otherwise clearly and specifically defined.

[0192] In the above embodiments, the description of each embodiment has its own emphasis. For parts that are not described in detail in a certain embodiment, reference can be made to the relevant descriptions of other embodiments.

[0193] The embodiments, implementation methods and related technical features of the present application can be combined and replaced with each other without conflict.

[0194] The above are only preferred embodiments of the present application and do not constitute any form of limitation to the present application. However, any simple modifications, equivalent changes and modifications made to the above embodiments based on the technical essence of the present application without departing from the content of the technical solution of the present application are still within the scope of the technical solution of the present application.

Claims

1. An organic compound, characterized in that The organic compound has a structural formula as shown in formula (1): （1）； Wherein, Ar1 is selected from at least one of the following groups: ； Each occurrence of Y1-Y8 is independently selected from N and CR4, and the dotted line represents the bond connecting Ar1 and L1; X is selected from CR5R6, C=C(R5R6), SiR5R6, NR5, C(=O), S, SO2, S(=O) or O; Ar2 is selected from a substituted or unsubstituted benzothiazolyl group having 7 to 30 carbon atoms; 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 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms; R1, R2, R3, R4, R5 and R6 are each independently selected from hydrogen, D, a straight chain alkyl group having 1 to 20 carbon atoms, a straight chain alkoxy group having 1 to 20 carbon atoms, a straight chain thioalkoxy group having 1 to 20 carbon atoms, a branched or cyclic alkyl group having 3 to 20 carbon atoms, a branched or cyclic alkoxy group having 3 to 20 carbon atoms, a branched or cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, At least one of 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; at least two adjacent groups among R1, R2, R3, R4, R5 and R6 are not ring-forming, or form an aliphatic, aromatic or heteroaromatic ring system having at least one ring with each other.

2. The organic compound according to claim 1, characterized in that Ar1 is selected from at least one of the following groups: 。 3. The organic compound according to claim 1, characterized in that Ar1 is selected from at least one of the following groups: ； wherein the H atom on the Ar1 ring is unsubstituted or substituted by R7; R7, at each occurrence, is independently selected from D, a linear alkyl group having 1 to 20 carbon atoms, a linear alkoxy group having 1 to 20 carbon atoms, a linear thioalkoxy group having 1 to 20 carbon atoms, a branched or cyclic alkyl group having 3 to 20 carbon atoms, a branched or cyclic alkoxy group having 3 to 20 carbon atoms, a branched or cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, a cyano group, a The invention relates to at least one of an R7 group, a carbamoyl group, a haloformyl group, a formyl group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, a CF3 group, a Cl group, a Br group, a F group, 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; wherein at least two adjacent R7 groups are not cyclic or form an aliphatic, aromatic or heteroaromatic ring system having at least one ring with each other.

4. The organic compound according to claim 1, characterized in that Ar2 is selected from one of the following groups: ； The dotted line represents the bond between Ar2 and N, which is a single bond.

5. The organic compound according to claim 4, characterized in that Ar2 is selected from one of the following groups: 。 6. The organic compound according to claim 1, characterized in that X is selected from O or S.

7. The organic compound according to claim 1, characterized in that L1 is selected from a single bond or at least one of the following groups: ； wherein each occurrence of W is independently selected from N or CR8; R8, at each occurrence, is independently selected from hydrogen, D, a straight chain alkyl group having 1 to 20 carbon atoms, a straight chain alkoxy group having 1 to 20 carbon atoms, a straight chain thioalkoxy group having 1 to 20 carbon atoms, a branched or cyclic alkyl group having 3 to 20 carbon atoms, a branched or cyclic alkoxy group having 3 to 20 carbon atoms, a branched or cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, The invention further comprises at least one of an alkyl, 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; at least two adjacent R8s are not cyclic, or form an aliphatic, aromatic or heteroaromatic ring system having at least one ring with each other.

8. The organic compound according to any one of claims 1 to 7, characterized in that The organic compound is selected from any one of the following formulas (2-1) to (2-16): 。 9. The organic compound according to any one of claims 1 to 7, characterized in that The organic compound is selected from any one of the following formulas (3-1) to (3-16): 。 10. The organic compound according to any one of claims 1 to 7, characterized in that The organic compound is selected from any one of the following formulas (4-1) to (4-16): 。 11. A composition, characterized in that The composition comprises at least one organic solvent and at least one organic compound according to any one of claims 1 to 10.

12. An organic electronic device, characterized in that: include: a first electrode; a second electrode, arranged opposite to the first electrode; An organic functional layer, disposed between the first electrode and the second electrode; The light extraction layer is arranged on the side of the second electrode away from the organic functional layer. The material of the light extraction layer includes the organic compound described in any one of claims 1 to 10, or the material of the light extraction layer includes the composition described in claim 11.

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