Organic Compounds, Compositions, and Organic Electronic Devices

Abstract

This application relates to an organic compound, a composition, and an organic electronic device; the organic compound has a structural formula as shown in formula (1): (1); by adding large groups to the organic compound in this application, such as naphthyl benzothiazole, naphthylphenyl benzothiazole group, at least one phenyl benzoxazole or phenyl benzothiazole group, the glass transition temperature of the organic compound is increased, the thermal stability of the organic compound is improved, such that the organic compound has a high extinction coefficient in the ultraviolet band and a small extinction coefficient in the visible light range, and has a relatively high refractive index; when the organic compound provided in this 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.

Description

Technical Field

[0001] The present application relates to the technical field of organic electroluminescence, and particularly 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 devices, which generate excitons through the transfer and recombination of carriers between various functional layers, and rely on organic compounds or metal complexes with high quantum efficiency to emit light. They have the characteristics of self-luminance, high brightness, high efficiency, high contrast, high responsiveness, etc.

[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 device stability and current efficiency (such as the stacking of metal complexes in the emission layer, the refractive index matching between functional layers, etc.). In 2001, Hung et al. covered the surface of the metal cathode with a layer of about 50 nm of organic compound or inorganic compound to improve the device performance by controlling the thickness and refractive index. In 2003, Riel et al. had tried to evaporate an inorganic compound ZnSe with a high refractive index (n = 2.6) on the cathode to improve the light extraction efficiency by utilizing the refractive index difference between functional layers. However, due to the high evaporation temperature and slow evaporation rate of inorganic materials, such compounds have not been more widely used in organic electroluminescent devices.

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

[0005] Therefore, a new type of material for improving the light extraction efficiency of organic electroluminescent devices needs to be further developed. Summary of the Invention

[0006] Embodiments of the present application provide an organic compound, a composition, and an organic electronic device, which are used in the light extraction layer of an organic electronic device to improve the light extraction efficiency of the organic electronic device.

[0007] To achieve the above object, an embodiment of the present application provides an organic compound, and the organic compound has a structural formula shown in formula (1):

[0008] (1);

[0009] Wherein, Ar1 is selected from at least one of the following groups:

[0010] ;

[0011] Each occurrence of Y1 to Y8 is independently selected from N, CR4, and the dashed line represents the bond connecting Ar1 and L1;

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

[0013] Ar2 is selected from a substituted or unsubstituted benzothiazolyl group having 7 to 30 carbon atoms;

[0014] L1 is selected from a single bond, alkenyl, alkynyl, acyl, amide group, carbonyl, 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, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms;

[0015] Each occurrence of R1, R2, R3, R4, R5 and R6 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, silyl, 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, cyano, carbamoyl, halocarbonyl, formyl, isocyano, isocyanate group, thiocyanate group, isothiocyanate group, 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, a heteroaryloxy group having 5 to 60 ring atoms; at least two adjacent groups among R1, R2, R3, R4, R5 and R6 do not form a ring, or form an aliphatic, aromatic or heteroaromatic ring system having at least one ring with each other.

[0016] In one embodiment of the present application, Ar1 is selected from at least one of the following groups:

[0017] 。

[0018] In one embodiment of the present application, Ar1 is selected from at least one of the following groups:

[0019] ;

[0020] wherein: the H atom on the Ar1 ring is unsubstituted or substituted by R7;

[0021] Each occurrence of R7 is independently selected from at least one of 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 halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, 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; wherein at least two adjacent R7s do not form a ring or form an aliphatic, aromatic or heteroaromatic ring system having at least one ring with each other.

[0022] In one embodiment of the present application, Ar2 is selected from one of the following groups:

[0023]

[0024]

[0025]

[0026] ;

[0027] wherein the dashed line represents the bond connecting Ar2 to N and is a single bond.

[0028] In one embodiment of the present application, Ar2 is selected from one of the following groups:

[0029]

[0030]

[0031]

[0032] 。

[0033] In one embodiment of the present application, X is selected from O or S.

[0034] In one embodiment of the present application, L1 is selected from a single bond or at least one of the following groups:

[0035] ;

[0036] wherein, each occurrence of W is independently selected from N or CR8;

[0037] Each occurrence of R8 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 halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, 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, a heteroaryloxy group having 5 to 60 ring atoms; at least two adjacent R8 do not form a ring, or form an aliphatic, aromatic or heteroaromatic ring system having at least one ring with each other.

[0038] In one embodiment of the present application, the organic compound is selected from any one of the following formulas (2-1) to (2-16):

[0039] 。

[0040] In one embodiment of the present application, the organic compound is selected from any one of the following formulas (3-1) to (3-16):

[0041] 。

[0042] In one embodiment of the present application, the organic compound is selected from any one of the following formulas (4-1) to (4-16):

[0043] 。

[0044] According to the above object 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 of the organic compounds.

[0045] According to the above object of the present application, an embodiment of the present application further provides an organic electronic device, which includes:

[0046] A first electrode;

[0047] A second electrode, disposed opposite to the first electrode;

[0048] An organic functional layer, disposed between the first electrode and the second electrode;

[0049] A light extraction layer, disposed on a side of the second electrode away from the organic functional layer, and the material of the light extraction layer includes the organic compound, or the material of the light extraction layer includes the composition.

[0050] In the present application, by adding large groups to the organic compound, such as naphthyl benzothiazole, naphthylphenyl benzothiazole group, at least one phenyl benzoxazole or phenyl benzothiazole group, the glass transition temperature of the organic compound is increased, the thermal stability of the organic compound is improved, so that the organic compound has a high extinction coefficient in the ultraviolet band and a small extinction coefficient in the visible light range, and has a high refractive index; when the organic compound provided by the present application is used as the material of the light extraction layer of the organic electronic device, it can avoid the adverse effects of harmful light on the internal materials of the device and improve the light extraction efficiency of visible light.

[0051] Other features and advantages of the present application will be described in detail in the subsequent specific implementation part. Description of the Drawings

[0052] To more clearly illustrate the technical solutions in the embodiments of the present application, the following will briefly introduce the drawings required for the description of the embodiments. Obviously, the drawings in the following description are only some embodiments of the present application. For those skilled in the art, without creative efforts, other drawings can also be obtained based on these drawings.

[0053] To more fully understand the present application and its beneficial effects, the following will be described in conjunction with the drawings, where the same reference numerals in the following description represent the same parts.

[0054] Figure 1 It is a schematic structural diagram of an organic electronic device provided by an embodiment of the present application;

[0055] Figure 2 It is another schematic structural diagram of an organic electronic device provided by an embodiment of the present application;

[0056] Figure 3 It is the nuclear magnetic spectrum of organic compound M1 provided by an embodiment of the present application.

[0057] Description of reference numerals:

[0058] 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 implementation manners

[0059] To make the purpose, technical solutions and effects of the present application clearer and more definite, the following further details the present application. 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.

[0060] In the present application, "substituted" means that the hydrogen atom in the substituent is replaced by the substituent.

[0061] In the present application, "number of ring atoms" refers to the number of atoms in the atoms that form the ring itself of a structural compound obtained by bonding atoms in a ring (for example, monocyclic compound, polycyclic compound, crosslinked compound, carbocyclic compound, heterocyclic compound). When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "number of ring atoms" described below without special instructions. 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 thiophene group is 5.

[0062] In the present application, "adjacent groups" means that these groups are bonded to the same carbon atom or adjacent carbon atoms. These definitions correspondingly apply to "adjacent substituents".

[0063] An aromatic group refers to a hydrocarbon group containing at least one aromatic ring. 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 particularly preferably selected from Si, N, P, O, and / or S. A fused-ring aromatic group means that the ring of the aromatic group can have two or more rings, where two carbon atoms are shared by two adjacent rings, that is, a fused ring. A fused hetero-ring aromatic group refers to a fused-ring aromatic hydrocarbon group containing at least one heteroatom. For the purposes of this application, an aromatic group or a heteroaromatic group includes not only the system 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 aromatic groups or hetero-ring aromatic groups for this purpose. For the purposes of this application, a fused-ring aromatic or fused hetero-ring aromatic ring system includes not only the system of aromatic groups or heteroaromatic groups, but also, in which multiple aromatic groups or hetero-ring aromatic groups can also be interrupted by short non-aromatic units (such as C, N, or O atoms). Therefore, systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, etc. are also considered fused-ring aromatic ring systems for this purpose.

[0064] An embodiment of this application provides an organic compound, and the organic compound has a structural formula as shown in formula (1):

[0065] (1);

[0066] Wherein, Ar1 is selected from at least one of the following groups:

[0067] ;

[0068] Each occurrence of Y1 to Y8 is independently selected from N, CR4, and the dashed line represents the bond connecting Ar1 and L1;

[0069] X is selected from CR5R6, C=C(R5R6), SiR5R6, NR5, C(=O), S, SO2, S(=O), or O;

[0070] Ar2 is selected from a benzothiazolyl group with 7 to 30 carbon atoms, which may or may not be substituted;

[0071] 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, an alkyl group with 1 to 60 carbon atoms, which may or may not be substituted, an alkoxy group with 1 to 60 carbon atoms, which may or may not be substituted, an aromatic group with 5 to 60 ring atoms, which may or may not be substituted, a heteroaromatic group with 5 to 60 ring atoms, which may or may not be substituted;

[0072] Each occurrence of R1, R2, R3, R4, R5, and R6 is independently selected from at least one of 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 halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, 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 do not form a ring, or form an aliphatic, aromatic, or heteroaromatic ring system having at least one ring with each other.

[0073] In the process of implementation and application, the present application increases large groups in the organic compound, such as naphthyl benzothiazole, naphthylphenyl benzothiazole group, at least one phenyl benzoxazole or phenyl benzothiazole group, thereby increasing the glass transition temperature of the organic compound, improving the thermal stability of the organic compound, making the organic compound have a high extinction coefficient in the ultraviolet band and a small extinction coefficient in the visible light range, and having a high refractive index; when the organic compound provided by the present application is used as the 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.

[0074] Specifically, in some embodiments, at least one of Y1 to Y4 is N.

[0075] In a preferred embodiment, Y1 or Y4 among Y1 to Y4 contained in Ar1 is N; more preferably, at least two of Y1 to Y4 are N; most preferably, Y1 and Y4 are both N at the same time.

[0076] In a preferred embodiment, at least one of Y5 to Y8 contained in Ar1 is N; more preferably, at least two of Y5 to Y8 are N; most preferably, Y5 and Y8 are both N at the same time.

[0077] Since the number of N atoms among Y1 to Y8 affects the electron-withdrawing ability of the group, the N atom can enhance the electron-withdrawing ability of the group, improve the electron push-pull of the whole molecule, regulate the energy level and dipole moment of the molecule, and improve the ultraviolet absorption of the molecule below 400 nm wavelength and the refractive index of the molecule.

[0078] In some embodiments, Ar1 is selected from at least one of the following groups:

[0079] .

[0080] More preferably, Ar1 is selected from at least one of the following groups:

[0081] .

[0082] In some embodiments, Y1 to Y4 are selected in the embodiments of the present application, and Ar1 is selected from at least one of the following groups:

[0083] .

[0084] Wherein, the H atom on the Ar1 ring is unsubstituted or substituted by R7;

[0085] Each occurrence of R7 is independently selected from 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 halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, 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, a heteroaryloxy group having 5 to 60 ring atoms; wherein at least two adjacent R7s do not form a ring or form an aliphatic, aromatic or heteroaromatic ring system having at least one ring with each other.

[0086] In some embodiments, the H atom on the Ar1 ring is unsubstituted.

[0087] Furthermore, in some embodiments, Ar1 is selected from at least one of the following groups:

[0088] .

[0089] More preferably, Ar1 is selected from at least one of the following groups:

[0090] .

[0091] In some embodiments, Ar2 is selected from one of the following groups:

[0092]

[0093]

[0094]

[0095] 。

[0096] Among them, the dashed line represents the bond connecting Ar2 and N, and it is a single bond. Any carbon on Ar2 can be connected to nitrogen.

[0097] In some embodiments, Ar2 is selected from one of the following groups:

[0098]

[0099]

[0100]

[0101] 。

[0102] More preferably, Ar2 is selected from one of the following groups:

[0103]

[0104] 。

[0105] In some embodiments, X is selected from O or S.

[0106] In some embodiments, L1 is selected from a single bond or at least one of the following groups:

[0107] ;

[0108] Among them, each occurrence of W is independently selected from N or CR8.

[0109] Each occurrence of R8 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 halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, 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, a heteroaryloxy group having 5 to 60 ring atoms; at least two adjacent R8 do not form a ring, or form an aliphatic, aromatic or heteroaromatic ring system having at least one ring with each other.

[0110] In some embodiments, L1 is selected from a single bond or one or a combination of the following groups:

[0111]

[0112]

[0113]

[0114]

[0115] 。

[0116] Wherein, the H atoms on the ring can be further substituted.

[0117] Furthermore, L1 is selected from one or a combination of the following groups:

[0118] 。

[0119] Wherein, the H atoms on the ring can be further substituted.

[0120] More preferably, L1 is selected from 。

[0121] Continuing from the above, in some embodiments, the organic compound is selected from any one of the following formulas (2-1) to (2-16):

[0122] 。

[0123] Furthermore, in the embodiments of the present application, L1 is selected, and the organic compound is selected from any one of the following formulas (3-1) to (3-16):

[0124] 。

[0125] Still further, in some embodiments, the organic compound is selected from any one of the following formulas (4-1) to (4-16):

[0126] 。

[0127] In some embodiments, Y1 - Y4 are all CH.

[0128] In some embodiments, the structural formula of the organic compound provided by the embodiments of the present application is selected from one of the following compounds:

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144] 。

[0145] It should be noted that for the examples of the organic compounds of the present application listed above, the H in the structural formula can be further arbitrarily substituted, for example, by deuterium.

[0146] According to the organic compound provided by the embodiment of the present application, it has a relatively high glass transition temperature, which can improve the thermal stability of the compound.

[0147] In some embodiments, the glass transition temperature T g is greater than or equal to 100 °C. In a preferred embodiment, T g is greater than or equal to 120 °C. In a more preferred embodiment, T g is greater than or equal to 140 °C. In a still more preferred embodiment, T g is greater than or equal to 160 °C. In a most preferred embodiment, T g is greater than or equal to 180 °C.

[0148] In some embodiments, the refractive index of the organic compound provided by 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.

[0149] In some embodiments, the singlet energy (S1) of the organic compound provided by 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.

[0150] The organic compound provided by the embodiments 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.

[0151] The organic compound provided by the embodiments of the present application has a high transmittance to visible light, reducing the impact on the light extraction efficiency of the device.

[0152] In some embodiments, the organic compound provided by the embodiments of the present application has a large extinction coefficient in the wavelength range of 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 most preferably greater than or equal to 1.0.

[0153] The organic compound provided by the embodiments of the present application can be used for the preparation of vapor deposition type OLEDs.

[0154] In some embodiments, the molecular weight of the organic compound provided by the embodiments of the present application is less than or equal to 1200 g / mol, the molecular weight of the organic compound provided by the embodiments of the present application is preferably less than or equal to 1100 g / mol, the molecular weight of the organic compound provided by 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 by 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 by the embodiments of the present application is most preferably less than or equal to 900 g / mol.

[0155] The organic compound provided by the embodiment of the present application can be used for the preparation of printed OLEDs.

[0156] In some embodiments, the molecular weight of the organic compound provided by the embodiment of the present application is greater than or equal to 800 g / mol, preferably greater than or equal to 900 g / mol, more preferably greater than or equal to 1000 g / mol, still more preferably greater than or equal to 1100 g / mol, and most preferably greater than or equal to 1200 g / mol.

[0157] In some other embodiments, the solubility of the organic compound provided by the embodiment of the present application in toluene at 25°C is 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.

[0158] Continuing from the above, the present application increases large groups in the organic compound, such as naphthyl benzothiazole, naphthylphenyl benzothiazole group, at least one phenyl benzoxazole or phenyl benzothiazole group, which improves the glass transition temperature of the organic compound, improves the thermal stability of the organic compound, makes the organic compound have a high extinction coefficient in the ultraviolet band and a small extinction coefficient in the visible light range, and has a high refractive index; when the organic compound provided by the present application is used as the 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.

[0159] For the above object of the present application, the embodiment of the present application also provides a composition, which includes at least one organic solvent and at least one of the organic compounds.

[0160] In some embodiments, the organic solvent is selected from aromatic or heteroaromatic, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, cycloaliphatic or olefinic compounds, or borate or phosphate compounds, or a mixture of two or more solvents.

[0161] In some embodiments, the organic solvent is selected from aromatic or heteroaromatic-based solvents, especially aliphatic chain / ring-substituted aromatic solvents, or aromatic ketone solvents, or aromatic ether solvents.

[0162] Examples of the organic solvents suitable for the present application include, but are not limited to: aromatic or heteroaromatic-based solvents: p-diisopropylbenzene, amylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylcumene, dipentylbenzene, tripentylbenzene, amyltoluene, 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-methylcumene, 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-(phenyloxiranyl)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, benzyl butylbenzene, 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-ethylbenzyl ethyl ether, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, 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, pentyl 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, alkanolactone, alkyl oleate, etc.

[0163] Further, in some embodiments, the organic solvent may be selected from: aliphatic ketones, such as 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, such as pentyl 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.

[0164] In other embodiments, the organic solvent may further 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.

[0165] In a preferred embodiment, the composition provided by the embodiments of the present application is a solution.

[0166] In another preferred embodiment, the composition provided by the embodiments of the present application is a suspension.

[0167] In the composition provided by the embodiments of the present application, the proportion of the organic compound in the composition may range from 0.01 to 20 wt%, preferably from 0.1 to 15 wt%, more preferably from 0.2 to 10 wt%, and most preferably from 0.25 to 5 wt% of the organic compound.

[0168] The composition provided by 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.

[0169] 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, blade coating, roller printing, reverse roller printing, lithographic printing, flexographic printing, rotary printing, spraying, brush coating or pad printing, slot die coating, etc. Gravure printing, nozzle printing and inkjet printing are preferred. The solution or suspension may additionally include one or more components such as surface active compounds, lubricants, wetting agents, dispersants, water repellents, adhesives, etc. for adjusting viscosity, film-forming properties, improving adhesion, etc. For detailed information on 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.

[0170] In addition, please refer to Figure 1 , the embodiments of the present application also provide an organic electronic device 100, and the organic electronic device 100 includes at least one compound as described above.

[0171] In some embodiments, the organic electronic device 100 may include an organic light-emitting diode, an organic photovoltaic cell, an organic light-emitting battery, an organic field-effect transistor, an organic light-emitting field-effect transistor, an organic laser, an organic spintronic device, an organic sensor, and an organic plasmonic emission diode, etc. An organic light-emitting diode is particularly preferred.

[0172] Preferably, the compound provided in the embodiments of the present application can be used as an electron transport layer material, a light-emitting layer host material or a light extraction layer material of an organic electronic device.

[0173] Furthermore, the organic electronic device 100 provided in the embodiments of the present application includes a first electrode 11, a second electrode 12, an organic functional layer 20, and a light extraction layer 30.

[0174] 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.

[0175] In some embodiments, the material of the light extraction layer 30 includes an organic compound represented by the formula (1) as described in the above embodiments, or the composition.

[0176] In some embodiments, the organic electronic device 100 may be an organic light-emitting diode device, 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 disposed on the surface of the cathode away from the light-emitting layer 23, or the light extraction layer 30 may also be disposed on the surface of the anode away from the light-emitting layer 23.

[0177] 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.

[0178] In some embodiments, the organic compound in the material of the light extraction layer 30 has a high glass transition temperature, which can improve the thermal stability of the organic compound. In some preferred embodiments, its glass transition temperature T g is greater than or equal to 100 °C. In a preferred embodiment, T g is greater than or equal to 120 °C. In a more preferred embodiment, T g is greater than or equal to 140 °C. In a still more preferred embodiment, T g is greater than or equal to 160 °C. In a most preferred embodiment, T g is greater than or equal to 180 °C.

[0179] Since the organic compound in the material of the light extraction layer 30 has a high refractive index, the light extraction layer 30 has a high 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 630 nm is greater than or equal to 1.7; preferably, the refractive index of the light extraction layer 30 at a wavelength of 630 nm is greater than or equal to 1.78; more preferably, the refractive index of the light extraction layer 30 at a wavelength of 630 nm is greater than or equal to 1.83.

[0180] In some embodiments, the singlet energy (S1) included in the light extraction layer 30 is greater than or equal to 2.7 eV; preferably, the singlet energy (S1) included in the light extraction layer 30 is greater than or equal to 2.8 eV; more preferably, the singlet energy (S1) included in the light extraction layer 30 is greater than or equal to 2.85 eV.

[0181] In some other embodiments, the singlet energy (S1) included in the light extraction layer 30 is less than or equal to 3.1 eV; preferably, the singlet energy (S1) included in the light extraction layer 30 is less than or equal to 3.0 eV.

[0182] 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 influence on the light extraction efficiency of the device.

[0183] In some embodiments, please refer to Figure 2 , the organic electronic device 100 is an electroluminescent device, and the organic electronic device further includes a substrate 40, the first electrode 11 is disposed on the substrate 40, the organic functional layer 20 is disposed on a side of the first electrode 11 away from the substrate 40, the second electrode 12 is disposed on a side of the organic functional layer 20 away from the first electrode 11, and the light extraction layer 30 is disposed on a side of the second electrode 12 away from the organic functional layer 20.

[0184] 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 that are sequentially disposed on a side of the first electrode 11 away from the substrate 40, and the number of the light emitting layers 23 can be at least one layer.

[0185] The organic electronic device 100 is preferably selected from an organic light emitting diode (Organic Light Emitting Display, OLED), an organic light emitting battery (Light-Emitting electrochemical cells, OLEEC), an organic field effect transistor (Organic Field-Effect Transistor, OFET), and an organic light emitting field effect transistor.

[0186] The following will describe in detail the film layer structures in the organic electronic device 100.

[0187] In some embodiments, the first electrode 11 may include a conductive metal, metal oxide, or conductive polymer. The first electrode 11 can easily inject holes into the hole injection layer 21 (HIL), hole transport layer 22, or 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 level or valence band level of the light-emitting body in the light-emitting layer 23 or the p-type semiconductor material serving as the hole injection layer 21, hole transport layer 22, or 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 of ordinary skill 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 pattern-structured. For example, a patterned ITO conductive substrate is commercially available and can be used to fabricate the organic electronic device 100 according to the embodiments of the present application.

[0188] In some embodiments, the second electrode 12 may include a conductive metal or metal oxide. The second electrode 12 can easily inject electrons into the electron injection layer 25, 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 level or conduction band 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, electron transport layer 24, or 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 the cathode of an OLED can potentially be used as the material of the second electrode 12 in the embodiments of the present application. The material of the second electrode 12 includes but is 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 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.

[0189] In some embodiments, the light extraction layer 30 has strong absorption in the region where the wavelength is less than 400 nm, and has weak or near-zero absorption in the visible light range where the wavelength is greater than 400 nm. Thus, it is possible to avoid damage to the materials inside the organic electronic device 100 caused by irradiation with high-energy light rays during subsequent processes. At the same time, the light extraction layer 30 has a relatively high refractive index, which can beneficially extract the emission of visible light and improve the light-emitting 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 1.50 or more at 630 nm, more preferably the refractive index of the light extraction layer 30 is 1.70 or more at 630 nm, and particularly preferably the refractive index of the light extraction layer 30 is 1.80 or more at 630 nm.

[0190] In some embodiments, the thickness range of the light extraction layer 30 is 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.

[0191] Embodiments of the present application also relate to the application of the organic electronic device 100 in various electronic devices, such as display devices, lighting devices, light sources, sensors, and the like.

[0192] The preparation process of the organic compound provided in the embodiments of the present application will be described below in conjunction with preferred embodiments. However, the embodiments of the present application are not limited to the following embodiments. It should be understood that the appended claims define the scope of the embodiments of the present application. Under the guidance of the concept of the present application, those skilled in the art should be aware 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

[0194] The following are examples of the synthesis method of the organic compound provided in the embodiments of the present application, but the present application is not limited to the following embodiments.

[0195] Synthesis of organic compound M1:

[0196]

[0197] Synthesis of organic compound M1:

[0198] Dissolve intermediate 1-1 (10 mmol), compound 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene, stir at 100 °C for 6 h under a nitrogen atmosphere; after the reaction solution is cooled, rotary evaporate to remove the solvent, extract the reaction solution and wash and separate with water, and subject the organic phase to column chromatography and recrystallization to obtain 9.15 mmol of organic compound M1, yield: 91.5%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of organic compound M1: MS(ASAP) = 662. And the NMR spectrum of organic compound M1 is as shown in Figure 3 shown.

[0199] Synthesis of organic compound M2:

[0200]

[0201] Synthesis of organic compound M2:

[0202] Dissolve intermediate 1-1 (10 mmol), compound 2-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene, stir at 100 °C for 6 h under a nitrogen atmosphere; after the reaction solution is cooled, rotary evaporate to remove the solvent, extract the reaction solution and wash and separate with water, and subject the organic phase to column chromatography and recrystallization to obtain 8.33 mmol of organic compound M2, yield: 83.3%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of organic compound M2: MS(ASAP) = 662.

[0203] Synthesis of organic compound M3:

[0204]

[0205] Synthesis of organic compound M3:

[0206] Intermediate 1-1 (10 mmol), compound 3-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-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 the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water and separated, and the organic phase was subjected to column chromatography and recrystallization to obtain 8.15 mmol of organic compound M3, yield: 81.5%, and the atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M3: MS(ASAP) = 738.

[0207] Synthesis of organic compound M4:

[0208]

[0209] Synthesis of organic compound M4:

[0210] Intermediate 1-1 (10 mmol), compound 4-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-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 the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water and separated, and the organic phase was subjected to column chromatography and recrystallization to obtain 8.07 mmol of organic compound M4, yield: 80.7%, and the atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M4: MS(ASAP) = 738.

[0211] Synthesis of organic compound M5:

[0212]

[0213] Synthesis of organic compound M5:

[0214] Intermediate 1-1 (10 mmol), compound 5-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-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 the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water and separated, and the organic phase was subjected to column chromatography and recrystallization to obtain 8.57 mmol of organic compound M5, yield: 85.7%, and the atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M5: MS(ASAP) = 738.

[0215] Synthesis of organic compound M6:

[0216]

[0217] Synthesis of intermediate 6-3:

[0218] Dissolve intermediate 6-1 (10 mmol), compound 6-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene, stir at 100 °C for 6 h under a nitrogen atmosphere; after the reaction solution is cooled, rotary evaporate to remove the solvent, extract the reaction solution and wash and separate with water, and subject the organic phase to column chromatography and recrystallization to obtain 9.14 mmol of intermediate 6-3, yield: 91.4%, atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate 6-3: MS(ASAP) = 403.

[0219] Synthesis of organic compound M6:

[0220] Dissolve intermediate 6-3 (10 mmol), compound 6-4 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene, stir at 100 °C for 6 h under a nitrogen atmosphere; after the reaction solution is cooled, rotary evaporate to remove the solvent, extract the reaction solution and wash and separate with water, and subject the organic phase to column chromatography and recrystallization to obtain 8.32 mmol of organic compound M6, yield: 83.2%, atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of organic compound M6: MS(ASAP) = 738.

[0221] Synthesis of organic compound M7:

[0222]

[0223] Synthesis of organic compound M7:

[0224] Dissolve intermediate 6-3 (10 mmol), compound 7-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene, stir at 100 °C for 6 h under a nitrogen atmosphere; after the reaction solution is cooled, rotary evaporate to remove the solvent, extract the reaction solution and wash and separate by liquid, and perform column chromatography and recrystallization on the organic phase to obtain 9.05 mmol of organic compound M7 with a yield of 90.5%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of organic compound M7: MS(ASAP) = 738.

[0225] Synthesis of organic compound M8:

[0226]

[0227] Synthesis of intermediate 8-3:

[0228] Dissolve intermediate 8-1 (10 mmol), compound 8-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene, stir at 100 °C for 6 h under a nitrogen atmosphere; after the reaction solution is cooled, rotary evaporate to remove the solvent, extract the reaction solution and wash and separate by liquid, and perform column chromatography and recrystallization on the organic phase to obtain 7.49 mmol of intermediate 8-3 with a yield of 74.9%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate 8-3: MS(ASAP) = 403.

[0229] Synthesis of organic compound M8:

[0230] Dissolve intermediate 8-3 (10 mmol), compound 6-4 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene, stir at 100 °C for 6 h under a nitrogen atmosphere; after the reaction solution is cooled, rotary evaporate to remove the solvent, extract the reaction solution and wash and separate by liquid, and perform column chromatography and recrystallization on the organic phase to obtain 8.15 mmol of organic compound M8 with a yield of 81.5%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of organic compound M8: MS(ASAP) = 738.

[0231] Synthesis of organic compound M9:

[0232]

[0233] Synthesis of organic compound M9:

[0234] Dissolve intermediate 9-1 (10 mmol), compound 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene, stir at 100 °C for 6 h under a nitrogen atmosphere; after the reaction solution cools, rotary evaporate to remove the solvent, extract the reaction solution and wash and separate with water, subject the organic phase to column chromatography and recrystallization to obtain organic compound M9 with a molar amount of 8.54 mmol and a yield of 85.4%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M9: MS(ASAP) = 694.

[0235] Synthesis of organic compound M10:

[0236]

[0237] Synthesis of organic compound M10:

[0238] Dissolve intermediate 9-1 (10 mmol), compound 2-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene, stir at 100 °C for 6 h under a nitrogen atmosphere; after the reaction solution cools, rotary evaporate to remove the solvent, extract the reaction solution and wash and separate with water, subject the organic phase to column chromatography and recrystallization to obtain organic compound M10 with a molar amount of 9.15 mmol and a yield of 91.5%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M10: MS(ASAP) = 694.

[0239] Synthesis of organic compound M11:

[0240]

[0241] Synthesis of organic compound M11:

[0242] Dissolve intermediate 9-1 (10 mmol), compound 3-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene, stir at 100 °C for 6 h under a nitrogen atmosphere; after the reaction solution is cooled, rotary evaporate to remove the solvent, extract the reaction solution and wash and separate with water, and subject the organic phase to column chromatography and recrystallization to obtain organic compound M11 with a molar amount of 7.68 mmol and a yield of 76.8%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M11: MS(ASAP) = 770.

[0243] Synthesis of organic compound M12:

[0244]

[0245] Synthesis of organic compound M12:

[0246] Dissolve intermediate 9-1 (10 mmol), compound 4-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene, stir at 100 °C for 6 h under a nitrogen atmosphere; after the reaction solution is cooled, rotary evaporate to remove the solvent, extract the reaction solution and wash and separate with water, and subject the organic phase to column chromatography and recrystallization to obtain organic compound M11 with a molar amount of 7.22 mmol and a yield of 72.2%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M12: MS(ASAP) = 770.

[0247] Synthesis of organic compound M13:

[0248]

[0249] Synthesis of organic compound M13:

[0250] Dissolve intermediate 9-1 (10 mmol), compound 13-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) in toluene, and stir at 100 °C for 6 h under a nitrogen atmosphere; after the reaction solution cools, rotary evaporate to remove the solvent, extract the reaction solution, wash with water and separate the layers, and subject the organic phase to column chromatography and recrystallization to obtain 8.29 mmol of compound M9, yield: 82.9%. The atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M13: MS(ASAP) = 678.

[0251] Energy structure of organic compounds:

[0252] The energy levels of organic compounds can be obtained by quantum calculations, such as using TD-DFT (time-dependent density functional theory) through Gaussian09W (Gaussian Inc.). For specific simulation methods, reference can be made to WO2011141110. First, use the semi-empirical method "Ground State / DFT / Default Spin / B3LYP / 6-31G(d)" (Charge0 / Spin Singlet) to optimize the molecular geometry structure, 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).

[0253] Deposit the compound on a single-crystalline silicon by vacuum evaporation to form a 50-nm thin film. Place the single-crystalline silicon on the sample stage of an ellipsometer (ES-01), with an incident angle of 70°. The test is carried out in an atmospheric environment. The extinction coefficient (k) and refractive index (n) test results of the compound are obtained from the ellipsometer, and the data are shown in Table 1.

[0254] Table 1

[0255]

[0256] 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 the damage of external high-energy light to the inside of the device. It has a higher refractive index than compound CBP in the comparative example, and the higher refractive index can ensure that the obtained light extraction layer 30 has a better light extraction effect.

[0257] Furthermore, in the organic compound provided by the embodiments of the present application, phenyl benzoxazole and phenyl (naphthyl) benzothiazole are contained in all three substituents connecting to N, which can further enhance the refractive index, and the raw materials are easily obtained and easy to purify.

[0258] Preparation and Characterization of OLED Devices:

[0259] The following will specifically illustrate the preparation process of the organic electronic device 100 as Figure 2 shown. The structure of the organic electronic device 100 is: ITO / Ag / ITO (the first electrode 11) / HATCN (hole injection layer 21) / SFNFB (hole transport layer 22) / m-CP:Ir(p-ppy)3 (light-emitting layer 23) / NaTzF2 (electron transport layer 24) / LiF (electron injection layer 25) / Mg:Ag (the second electrode 12) / light extraction layer 30. The preparation steps are as follows:

[0260] Device Example 1: Clean the ITO conductive glass anode layer (the first electrode 11), and 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, deposit the hole injection layer material HATCN by vacuum evaporation, with a thickness of 5 nm and an evaporation rate of 1 Å / s. On the hole injection layer 21, deposit the hole transport material SFNFB by vacuum evaporation, with a thickness of 80 nm. Deposit the light-emitting layer 23 on the hole transport layer 22. m-CP is used as the host material and Ir(p-ppy)3 is used as the doping material. The mass ratio of Ir(p-ppy)3 to m-CP is 1:9, and the thickness is 30 nm. Deposit the electron transport material NaTzF2 by vacuum evaporation on the light-emitting layer 23, with a thickness of 30 nm. Deposit the electron injection layer LiF by vacuum evaporation on the electron transport layer 24, with a thickness of 1 nm, and this layer is the electron injection layer 25. Deposit the cathode Mg:Ag layer (the second electrode 12) by vacuum evaporation on the electron injection layer 25. The doping ratio of Mg:Ag is 9:1, and the thickness is 15 nm. Deposit the organic compound M1 by vacuum evaporation on the second electrode 12 to obtain the light extraction layer 30, with a thickness of 60 nm.

[0261] Device Example 2: The organic compound in the light extraction layer 30 of the organic electronic device 100 is changed to M2.

[0262] Device Example 3: The organic compound in the light extraction layer 30 of the organic electronic device 100 is changed to M3.

[0263] Device Example 4: The organic compound in the light extraction layer 30 of the organic electronic device 100 is changed to M4.

[0264] Device Example 5: The organic compound in the light extraction layer 30 of the organic electronic device 100 becomes M5.

[0265] Device Example 6: The organic compound in the light extraction layer 30 of the organic electronic device 100 becomes M6.

[0266] Device Example 7: The organic compound in the light extraction layer 30 of the organic electronic device 100 becomes M7.

[0267] Device Example 8: The organic compound in the light extraction layer 30 of the organic electronic device 100 becomes M8.

[0268] Device Example 9: The organic compound in the light extraction layer 30 of the organic electronic device 100 becomes M9.

[0269] Device Example 10: The organic compound in the light extraction layer 30 of the organic electronic device 100 becomes M10.

[0270] Device Example 11: The organic compound in the light extraction layer 30 of the organic electronic device 100 becomes M11.

[0271] Device Example 12: The organic compound in the light extraction layer 30 of the organic electronic device 100 becomes M12.

[0272] Device Example 13: The organic compound in the light extraction layer 30 of the organic electronic device 100 becomes M13.

[0273] Device Comparative Example 1: The organic compound in the light extraction layer 30 of the organic electronic device 100 becomes CBP.

[0274] The chemical structures of the compounds involved in the devices are as follows:

[0275] .

[0276] The luminous efficiency data of Device Examples 1 to 13 and Device Comparative Example 1 are shown in Table 2.

[0277] Table 2

[0278]

[0279] Among them, the luminous efficiency in Table 2 is at a current density of 10 mA / cm 2The data obtained at that time. As can be seen from Table 2, compared with the device comparative example 1, when the organic compound provided in the embodiment of the present application is used as the light extraction layer 30, the light emission efficiency of the organic electronic device 100 can be effectively improved. This is because compared with the organic compound CBP of the light extraction layer 30 in the device comparative example 1, the present application increases large groups in the organic compound, such as naphthyl benzothiazole, naphthylphenyl benzothiazole group, at least one phenyl benzoxazole or phenyl benzothiazole group, which improves the glass transition temperature of the organic compound, improves the thermal stability of the organic compound, makes the organic compound have a high extinction coefficient in the ultraviolet band and a small extinction coefficient in the visible light range, and has a high 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 light extraction efficiency of visible light.

[0280] In addition, the embodiment of the present application also provides a display panel, and the display panel includes the organic electronic device as described in the above embodiment.

[0281] 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 elaborated here.

[0282] In the description of the present application, the terms "first" and "second" are only used for descriptive purposes, and cannot be understood as indicating or implying relative importance or implicitly specifying the quantity of the indicated technical features. Thus, the features defined with "first" and "second" may explicitly or implicitly include one or more features. In the description of the present application, "a plurality" means two or more, unless otherwise specifically defined.

[0283] In the above embodiments, the descriptions of the respective embodiments have their own emphases. For the parts not detailed in a certain embodiment, reference may be made to the relevant descriptions of other embodiments.

[0284] Among the embodiments, embodiments, and related technical features of the present application, they can be combined and replaced with each other without conflict.

[0285] The above are only the preferred embodiments of the present application, and do not impose any form of limitation on the present application. However, any simple modification, equivalent change, and modification 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 still fall 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 shown in formula (1): （1）； Wherein, Ar1 is selected from at least one of the following groups: ； X is selected from S or O, and when X is selected from S, Ar1 is not ; Ar2 is selected from any one of the following groups: ； L1 is selected from ; R1 is selected from hydrogen.

2. The organic compound according to claim 1, wherein The organic compound is selected from any one of the following: 。 3. The organic compound according to claim 1, wherein The organic compound is selected from any one of the following: 。 4. A composition, characterized in that, The composition includes at least one organic solvent and at least one organic compound according to any one of claims 1 to 3.

5. An organic electronic device, characterized in that, Comprising: A first electrode; A second electrode, disposed opposite to the first electrode; An organic functional layer, disposed between the first electrode and the second electrode; A light extraction layer, disposed on a side of the second electrode away from the organic functional layer, wherein the material of the light extraction layer includes the organic compound according to any one of claims 1 to 3, or the material of the light extraction layer includes the composition according to claim 4.

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