An organic compound and use thereof in organic electronic devices

Abstract

Disclosed are an organic compound and its application in an organic electronic device, particularly in an organic electroluminescent diode. Also disclosed are an organic electronic device, particularly an organic electroluminescent diode, comprising the organic compound according to the present application, a preparation method thereof and its application in display and lighting technology. The compound according to the present application has high thermal stability, and can improve the luminous efficiency and lifetime of the device.

Description

TECHNICAL FIELD

[0001] The present application relates to an organic electronic material and device technology, in particular to an organic compound, a mixture comprising the same, a composition, and an organic electronic device thereof, and particularly to the use thereof in an organic electronic device. BACKGROUND

[0002] OLEDs have great potential in the application of optoelectronic devices (e.g. flat panel displays and lighting) due to the diversity of synthetic organic semiconductors, the relatively low cost of fabrication and the excellent optical and electronic properties.

[0003] An organic electroluminescence phenomenon refers to a phenomenon in which organic substances convert electrical energy into light energy. An organic electroluminescence device using the organic electroluminescence phenomenon generally has a structure of a positive electrode and a negative electrode and an organic layer therebetween. In order to improve the efficiency and lifespan of the organic electroluminescence device, the organic layer has a multi-layer structure, each layer of which comprises a different organic substance. Specifically, it can include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. In such an organic electroluminescence device, when a voltage is applied between the two electrodes, holes are injected from the positive electrode to the organic layer and electrons are injected from the negative electrode to the organic layer, and when the injected holes and electrons meet, an exciton is formed, and light is emitted when the exciton transitions to a ground state. Such an organic electroluminescence device has characteristics of self-emission, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, high response, etc.

[0004] Although a large number of OLED materials have been developed, there are still many problems. How to design new materials with better performance for adjustment, such as high-performance electron transport materials, so as to achieve the effect of reducing device voltage and improving device efficiency and lifespan, has always been a problem to be solved by those skilled in the art. SUMMARY

[0005] In view of the deficiencies of the prior art described above, the purpose of the present application is to provide an organic compound, a mixture and a composition comprising the same, and the use thereof in an organic electronic device, aiming to solve the problem of low efficiency and lifespan of the existing organic electronic device.

[0006] The technical solution of the present application is as follows:

[0007] An organic compound has a structure as shown in general formula (I):

[0008]

[0009] wherein:

[0010] X is independently selected from N or CR7, and at least one X is N;

[0011] R1-R7are each independently in each occurrence selected from the group consisting of hydrogen, D, or a linear alkyl group having 1 to 20 C atoms, or a linear alkoxy group having 1 to 20 C atoms, or a linear thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl group having 3 to 20 C atoms, or a branched or cyclic alkoxy group having 3 to 20 C atoms, or a branched or cyclic thioalkoxy group having 3 to 20 C atoms, a silyl group, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a halogen formyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, CI, Br, F, a cross-linkable group, or a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or an aryloxy group having 5 to 60 ring atoms, or a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups;

[0012] L is selected from a single bond, or a substituted or unsubstituted aromatic or heteroaromatic group having 6 to 30 ring atoms;

[0013] m and n are each independently selected from 0, 1, and m+n > 1;

[0014] o is selected from any integer between 0 and 4, and p is selected from any integer between 0 and 3.

[0015] A polymer comprising at least one repeating unit, said repeating unit comprising a structure corresponding to the organic compound described above.

[0016] A mixture comprising one organic compound or polymer described above, and at least one other organic functional material selected from one or more of a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, an emitting material, a host material, an organic dye.

[0017] A composition comprising at least one organic compound or polymer or mixture described above, and at least one organic solvent.

[0018] An organic electronic device comprising a functional layer, said functional layer comprising at least one organic compound or polymer or mixture described above or prepared from the composition described above.

[0019] Beneficial effects: The organic compound of the present application can adjust the stacking between molecules due to the steric hindrance effect, is less likely to crystallize after film formation, and reduces the interaction between molecules, thereby reducing the exciton quenching and improving the energy utilization rate, so as to improve the efficiency and service life of related materials and devices. DETAILED DESCRIPTION

[0020] The present application provides an organic compound and its application in an organic electroluminescent device, and an organic electronic device comprising the organic compound and a preparation method thereof. In order to make the purpose, technical scheme and effect of the present application more clear and explicit, the present application is further described in detail below. It should be understood that the specific examples described herein are only used to explain the present application and do not limit the present application.

[0021] In the present application, composition and printing ink, or ink have the same meaning and can be interchangeable.

[0022] In the present application, aromatic group, aromatic, aromatic ring system have the same meaning and can be interchangeable.

[0023] In the present application, heteroaromatic group, heteroaromatic, heteroaromatic ring system have the same meaning and can be interchangeable.

[0024] In the present application, "substituted" means that the hydrogen atom in the substituent is replaced by the substituent.

[0025] In the present application, "ring atom number" means the number of atoms in the ring itself of a structural compound obtained by bonding atoms into a ring (for example, monocyclic compound, fused ring 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 "ring atom number" described below, unless otherwise specified. For example, the ring atom number of a benzene ring is 6, the ring atom number of a naphthalene ring is 10, and the ring atom number of a thiophene group is 5.

[0026] In the present application, aromatic ring system or aromatic group means a hydrocarbon group comprising at least one aromatic ring, including monocyclic groups and polycyclic ring systems. Heteroaromatic ring system or heteroaromatic group means a hydrocarbon group comprising at least one heteroaromatic ring (containing heteroatoms), including monocyclic groups and polycyclic ring systems. The heteroatoms are preferably selected from Si, N, P, O, S and / or Ge, particularly preferably from Si, N, P, O and / or S. These polycyclic rings can have two or more rings, in which two carbon atoms are shared by two adjacent rings, i.e. fused rings. Of these polycyclic rings, at least one is aromatic or heteroaromatic. For the purposes of the present application, aromatic groups or heteroaromatic groups not only include aromatic or heteroaromatic systems, but also, in which a plurality of aryl or heteroaromatic groups can also be interrupted by short non-aromatic units (< 10% of non-H atoms, preferably less than 5% of non-H atoms, such as C, N or O atoms). Thus, for example, systems such as 9,9'-spirobifluorene, 9,9-diaromatic fluorene, triarylamine, diaryl ether, etc. are also considered aromatic groups for the purposes of the present application.

[0027] Specific examples of aromatic groups are: benzene, naphthalene, anthracene, phenanthrene, rylenes, tetracene, pyrene, benzopyrene, triphenylene, acenaphthene, fluorene, and derivatives thereof.

[0028] Specific examples of heteroaromatic groups are: furan, benzofuran, thiophene, benzothiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thienopyrrole, thienothiophene, furanopyrrole, furanofuran, thienofuran, benzisoxazole, benzisothiazole, benzimidazole, pyridine, pyrazine, pyridazine, pyrimidine, triazine, quinoline, isoquinoline, perylene, quinoxaline, phenanthridine, berberine, quinazoline, quinazolinone, and derivatives thereof.

[0029] In the present application, "alkyl" can mean straight chain, branched chain, and / or cyclic alkyl. The number of carbons of alkyl can be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Non-limiting examples of alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, t-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, t-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-t-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, t-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethyihexadecyl, 2-butyihexadecyl, 2-hexyihexadecyl, 2-octyihexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyileicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, and the like.

[0030] The present application relates to an organic compound having a structure as shown in the general formula (I):

[0031]

[0032] wherein: X is independently selected from N or CR7, and at least one X is N; R1-R7 are each independently at each occurrence selected from: hydrogen, D, or a straight chain alkyl group having 1 to 20 C atoms, or a straight chain alkoxy group having 1 to 20 C atoms, or a straight chain thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl group having 3 to 20 C atoms, or a branched or cyclic alkoxy group having 3 to 20 C atoms, or a branched or cyclic thioalkoxy group having 3 to 20 C atoms, silyl, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, cyano, carbamoyl, halogenformyl, formyl, isocyano, isocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, a crosslinkable group, or a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or an aryloxy group having 5 to 60 ring atoms, or a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups; L is selected from a single bond, or a substituted or unsubstituted aromatic or heteroaromatic group having 6 to 30 ring atoms; m and n are each independently selected from 0, 1, and m+n > 1;

[0033] o is selected from any integer from 0 to 4, and p is selected from any integer from 0 to 3.

[0034] In some preferred embodiments, R1-R7 are each independently at each occurrence selected from hydrogen, D, cyano, a straight chain alkyl group having 1 to 18 C atoms, or a branched or cyclic alkyl, alkoxy, thioalkoxy, or silyl group having 3 to 18 C atoms, or a substituted or unsubstituted aromatic, heteroaromatic, aryloxy, or heteroaryloxy group having 5 to 30 ring atoms; in more preferred embodiments, R1-R7 are each independently at each occurrence selected from D, a straight chain alkyl group having 1 to 12 C atoms, or a substituted or unsubstituted aromatic, heteroaromatic, aryloxy, or heteroaryloxy group having 5 to 20 ring atoms; in most preferred embodiments, R1-R4 are each independently at each occurrence selected from D, a straight chain alkyl group having 1 to 6 C atoms, or a substituted or unsubstituted aromatic, heteroaromatic, aryloxy, or heteroaryloxy group having 5 to 15 ring atoms.

[0035] In some preferred embodiments, R1-R7 are each independently at each occurrence fully deuterated or partially deuterated.

[0036] In a preferred embodiment, the organic compound has a structure according to one of the general formulas (II-1) to (II-4):

[0037]

[0038] wherein the meaning of X, R1-R6, L, o, p, m, n are as described above.

[0039] In a more preferred embodiment, the organic compound has a structure according to formula (III-1) to (III-4):

[0040]

[0041] wherein the meaning of R1-R6, L, o, p, m, n are as described above.

[0042] In some preferred embodiments, L is selected from a single bond or the following groups:

[0043]

[0044] wherein: X2is independently selected from CR8or N at each occurrence; Y1is independently selected from NR9, CR 10 R 11 , O, S, SiR 12 R 13 , S=O, SO2or P(R 14 ); R8-R 13 are each independently at each occurrence selected from: hydrogen, D, or a linear alkyl group having 1 to 20 C atoms, or a linear alkoxy group having 1 to 20 C atoms, or a linear thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl group having 3 to 20 C atoms, or a branched or cyclic alkoxy group having 3 to 20 C atoms, or a branched or cyclic thioalkoxy group having 3 to 20 C atoms, a silyl group, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a halogen formyl 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 crosslinkable group, or a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, or 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, or a combination of these groups.

[0045] In some preferred embodiments, L, L1and L2are independently selected from the following groups or combinations thereof:

[0046]

[0047] wherein: the H atoms on the ring can be further substituted.

[0048] In some preferred embodiments, L is selected from a single bond or the following groups and combinations:

[0049]

[0050] wherein R 15 -R 42 have the meaning as described above for R1.

[0051] L is selected from the above-mentioned groups having a twisted structure, which can effectively prevent molecular packing, improve the stability of the material while reducing the evaporation temperature, and at the same time, due to the guarantee of the structure having good conjugation, improve the transmission ability of the material.

[0052] In one embodiment, R1-R6 are independently selected from the following groups and combinations thereof:

[0053]

[0054] wherein: X1is selected from N or CR 101 ; Y 1 is selected from O, S, S=O, SO2, NR 102 , CR 103 R 104 or SiR 105 R 106 ; R 101 -R 106 is independently selected at each occurrence from: hydrogen, D, or a linear alkyl group having 1 to 20 C atoms, or a linear alkoxy group having 1 to 20 C atoms, or a linear thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl group having 3 to 20 C atoms, or a branched or cyclic alkoxy group having 3 to 20 C atoms, or a branched or cyclic thioalkoxy group having 3 to 20 C atoms, a silyl group, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a halogen formyl 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 crosslinkable group, or a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or an aryloxy group having 5 to 60 ring atoms, or a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.

[0055] Further, R1-R6 are independently selected at each occurrence from the following groups:

[0056]

[0057]

[0058] These groups can optionally be substituted by 0, 1, 2 or 3 groups selected from D, F, CI, Br, cyano, C1-C4 alkyl, C1-C3 haloalkyl, phenyl, naphthyl, fluorenyl, spirofluorenyl and C3-C10 cycloalkyl. A1 is selected from a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or an aryloxy group having 5 to 60 ring atoms, or a heteroaryloxy group having 5 to 60 ring atoms.

[0059] In some embodiments, an organic compound according to the present application is preferably selected from, but not limited to, the following structures:

[0060]

[0061]

[0062]

[0063]

[0064]

[0065] In a preferred embodiment, the organic compound according to the present application has a glass transition temperature Tg > 100 °C, in a preferred embodiment Tg > 120 °C, in a more preferred embodiment Tg > 140 °C, in a further preferred embodiment Tg > 160 °C, and in a most preferred embodiment Tg > 180 °C.

[0066] In a more preferred embodiment, the organic compound according to the present application is partially deuterated, preferably 10% of the H are replaced by deuterium, more preferably 20% of the H are replaced by deuterium, very preferably 30% of the H are replaced by deuterium, and most preferably 40% of the H are replaced by deuterium.

[0067] In a preferred embodiment, the organic compound according to the present application is a small molecule material.

[0068] In a preferred embodiment, the organic compound according to the present application is used for the evaporation of an OLED device. For this purpose, the compound according to the present application has a molecular weight < 1000 g / mol, preferably < 900 g / mol, very preferably < 850 g / mol, more preferably < 800 g / mol, and most preferably < 700 g / mol.

[0069] The present application also relates to a method for the synthesis of an organic compound according to the general formula (I), wherein a reaction is carried out using a starting material which contains a reactive group. These reactive starting materials contain at least one leaving group, for example bromine, iodine, boronic acid or boronic acid ester. Suitable reactions for forming C-C linkages are well known to the person skilled in the art and are described in the literature. Particularly suitable and preferred coupling reactions are the SUZUKI, STILLE and HECK coupling reactions.

[0070] The present application also relates to a polymer which contains at least one repeating unit, wherein at least one of the repeating units contains a structure according to the general formula (I). In certain embodiments, the polymer is a non-conjugated polymer, wherein the structure according to the general formula (I) is present in the side chain. In another preferred embodiment, the polymer is a conjugated polymer. The term "small molecule" as defined herein means a molecule which is not a polymer, oligomer, dendrimer or blend. In particular, a small molecule does not contain repeating structures. The molecular weight of a small molecule is < 3000 g / mol, preferably < 2000 g / mol and most preferably < 1500 g / mol.

[0071] The term "polymer" includes homopolymers, copolymers and block copolymers. In addition, polymers in the present application also include dendrimers. For the synthesis and applications of dendrimers, see [Dendrimers and Dendrons, Wiley-VCH Verlag GmbH & Co. KGaA, 2002, Ed. George R. Newkome, Charles N. Moorefield, Fritz Vogtle.].

[0072] A conjugated polymer is a polymer whose backbone is mainly composed of sp2 hybridized carbon atoms. Well known examples are polyacetylene and poly(phenylenevinylene). The backbone of a conjugated polymer can also contain other atoms than carbon and it is still considered to be a conjugated polymer if the sp2 hybridization of the backbone is interrupted by natural defects. In addition, conjugated polymers in the present application also include polymers whose backbone contains aryl amines, aryl phosphines and other heteroarmotics, organometallic complexes, etc.

[0073] In a preferred embodiment, the synthesis of the high polymer is selected from the group consisting of SUZUKI-, YAMAMOTO-, STILLE-, NIGESHI-, KUMADA-, HECK-, SONOGASHIRA-, HIYAMA-, FUKUYAMA-, HARTWIG-BUCHWALD- and ULLMAN.

[0074] In a preferred embodiment, the high polymer according to the present application has a glass transition temperature (Tg) of ≥ 100 °C, preferably of ≥ 120 °C, more preferably of ≥ 140 °C, even more preferably of ≥ 160 °C, most preferably of ≥ 180 °C.

[0075] In a preferred embodiment, the high polymer according to the present application has a molecular weight distribution (PDI) in the range of preferably 1 to 5; more preferably 1 to 4; even more preferably 1 to 3, even more preferably 1 to 2, most preferably 1 to 1.5.

[0076] In a preferred embodiment, the high polymer according to the present application has a weight average molecular weight (Mw) in the range of preferably 100,000 to 1,000,000; more preferably 500,000 to 5,000,000; even more preferably 1,000,000 to 4,000,000; even more preferably 1,500,000 to 3,000,000; most preferably 2,000,000 to 2,500,000.

[0077] The present application also relates to a mixture comprising an organic compound as described above and at least one further organic functional material selected from the group consisting of hole injection materials (HIM), hole transport materials (HTM), electron transport materials (ETM), electron injection materials (EIM), electron blocking materials (EBM), hole blocking materials (HBM), emitters, host materials and organic dyes. Various organic functional materials are described in detail, for example, in WO 2010 / 135519 A1, US 2009 / 0137484 A1 and WO 201 1 / 1 10727 A1, the entire contents of which are hereby incorporated by reference. The organic functional material can be a small molecule and a high polymer material.

[0078] In a preferred embodiment, the mixture comprises an organic compound according to the present application and a phosphorescent emitter. Here, the organic compound according to the present application can act as host material and the phosphorescent emitter is present in an amount of ≤ 20 wt.-%, preferably ≤ 15 wt.-%, more preferably ≤ 10 wt.-%.

[0079] In another preferred embodiment, the mixture comprises an organic compound according to the present application, another host material and a phosphorescent emitter. Here the organic compound according to the present application acts as co-host material in a weight percentage of > 10 wt%, preferably > 20 wt%, more preferably > 30 wt%, most preferably > 40 wt%.

[0080] In a more preferred embodiment, the mixture comprises an organic compound according to the present application, a phosphorescent emitter and a host material. In this embodiment, the organic compound according to the present application can act as auxiliary emitter material in a weight ratio to the phosphorescent emitter of from 1 :2 to 2:1. In another preferred embodiment, the T1of the organic compound according to the present application is higher than the phosphorescent emitter.

[0081] In certain embodiments, the mixture comprises an organic compound according to the present application, and another TADF material.

[0082] In certain preferred embodiments, the mixture according to the present application comprises an organic functional material H1, selected from the group of organic compounds as described above, and at least another organic functional material H2, H2 being selected from the group of hole (also called electron hole) injecting or transporting materials (HIM / HTM), organic host materials (Host).

[0083] In certain preferred embodiments, the organic mixture according to the present application, wherein at least one of H1 and H2 has ((LUMO+1)-LUMO) > 0.2 eV, preferably > 0.25 eV, more preferably > 0.3 eV, even more preferably > 0.35 eV, very preferably > 0.4 eV, most preferably > 0.45 eV.

[0084] In a more preferred embodiment, the organic mixture according to the present application, wherein H1 has ((LUMO+1)-LUMO) > 0.2 eV, preferably > 0.25 eV, more preferably > 0.3 eV, even more preferably > 0.35 eV, very preferably > 0.4 eV, most preferably > 0.45 eV.

[0085] In certain preferred embodiments, the organic mixture according to the present application, wherein at least one of H1 and H2 has ((HOMO-(HOMO-1)) > 0.2 eV, preferably > 0.25 eV, more preferably > 0.3 eV, even more preferably > 0.35 eV, very preferably > 0.4 eV, most preferably > 0.45 eV.

[0086] In a preferred embodiment, the organic mixture according to the present application, wherein ((HOMO(H2) - HOMO(H1)) > 0.2 eV, preferably > 0.25 eV, more preferably > 0.3 eV, even more preferably > 0.35 eV, very preferably > 0.4 eV, most preferably > 0.45 eV.

[0087] In certain preferred embodiments, the organic mixture, wherein 1) ΔE(S1-T1) of H1 is ≤ 0.30 eV, preferably ≤ 0.25 eV, more preferably ≤ 0.20 eV, most preferably ≤ 0.10 eV, and / or 2) the LUMO of H2 is higher than the LUMO of H1 and the HOMO of H2 is lower than the HOMO of H1.

[0088] In certain preferred embodiments, the organic mixture, wherein H1 and H2 have a type II semiconductor heterojunction structure, and min((LUMO(H1) - HOMO(H2), LUMO(H2) - HOMO(H1)) ≤ min(ET(H1), ET(H2)) + 0.1 eV, wherein LUMO(H1), HOMO(H1) and ET(H1) are the lowest unoccupied orbital, the highest occupied orbital, and the triplet energy level of H1, respectively, and LUMO(H2), HOMO(H2) and ET(H2) are the lowest unoccupied orbital, the highest occupied orbital, and the triplet energy level of H2, respectively. More preferably, min((LUMO(H1) - HOMO(H2), LUMO(H2) - HOMO(H1)) ≤ min(ET(H1), ET(H2)). Even more preferably, min((LUMO(H1) - HOMO(H2), LUMO(H2) - HOMO(H1)) ≤ min(ET(H1), ET(H2)) - 0.1 eV.

[0089] In a preferred embodiment, H1 and H2 have a type I semiconductor heterojunction structure, and the difference between the singlet energy level and the triplet energy level (S1-T1) of H1 or H2 is less than or equal to 0.25 eV, preferably less than or equal to 0.20 eV, more preferably less than or equal to 0.15 eV, most preferably less than or equal to 0.10 eV.

[0090] In a preferred embodiment, the mixture, wherein the molar ratio of H1 and H2 is from 1:9 to 9:1, preferably from 2:8 to 8:2; preferably the molar ratio is from 3:7 to 7:3; more preferably the molar ratio is from 4:6 to 6:4; most preferably the molar ratio is from 4.5:5.5 to 5.5:4.5.

[0091] In a preferred embodiment, the mixture, wherein the difference in molecular weight of H1 and H2 is not more than 100 Dalton, preferably not more than 80 Dalton, more preferably not more than 70 Dalton, even more preferably not more than 60 Dalton, very preferably not more than 40 Dalton, most preferably not more than 30 Dalton.

[0092] In another preferred embodiment, the mixture, wherein the difference in sublimation temperature of H1 and H2 is not more than 50 K; preferably the difference in sublimation temperature is not more than 30 K; more preferably the difference in sublimation temperature is not more than 20 K; most preferably the difference in sublimation temperature is not more than 10 K.

[0093] In a preferred embodiment, at least one of H1 and H2 in the mixture according to the present application has a glass transition temperature Tg≥ 100 °C, in a preferred embodiment at least one of H1 and H2 has a Tg≥ 120 °C, in a more preferred embodiment at least one of H1 and H2 has a Tg≥ 140 °C, in an even more preferred embodiment at least one of H1 and H2 has a Tg≥ 160 °C, in a most preferred embodiment at least one of H1 and H2 has a Tg≥ 180 °C.

[0094] The organic compounds according to the present application can be used as functional materials in functional layers of electronic devices. Functional layers include, but are not limited to, hole injection layers (HIL), hole transport layers (HTL), electron transport layers (ETL), electron injection layers (EIL), electron blocking layers (EBL), hole blocking layers (HBL), and emission layers (EML).

[0095] In a preferred embodiment, the organic compounds according to the present application are used in an emission layer.

[0096] In a preferred embodiment, the organic compounds according to the present application are used in an electron transport layer.

[0097] The phosphorescent emitter (triplet emitter), the phosphorescent host material (triplet host material) and the TADF emitter are described in more detail below (but are not limited thereto).

[0098] 1. Triplet Host:

[0099] Examples of triplet host materials are not particularly limited, and any metal complex or organic compound can be used as a host as long as its triplet energy level is higher than that of an emitter, in particular, a triplet emitter or a phosphorescent emitter. Examples of metal complexes that can be used as a triplet host include, but are not limited to, the following general structures:

[0100] Examples of triplet host materials are not particularly limited, and any metal complex or organic compound can be used as a host as long as its triplet energy level is higher than that of an emitter, in particular, a triplet emitter or a phosphorescent emitter. Examples of metal complexes that can be used as a triplet host include, but are not limited to, the following general structures:

[0101] M3 is a metal; (Y3-Y4) is a bidentate ligand, Y3 and Y4 are independently selected from C, N, O, P, and S; L is an ancillary ligand; r2 is an integer having a value from 1 to the maximum coordination number of the metal.

[0102] In a preferred embodiment, the metal complex that can be used as a triplet host has the following form:

[0103]

[0104] (O-N) is a bidentate ligand in which the metal is coordinated to O and N atoms, and r2 is an integer having a value from 1 to the maximum coordination number of the metal.

[0105] In one embodiment, M3 is selected from Ir and P.

[0106] Examples of organic compounds that can be used as triplet host are selected from the group consisting of compounds containing a cyclic aromatic hydrocarbon group, such as benzene, biphenyl, triphenylbenzene, benzofluorene; compounds containing an aromatic heterocyclic group, such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, dibenzocarbazole, indolocarbazole, pyridinoindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, oxazole, dibenzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, phthalazine, quinazoline, quinoxaline, naphthalene, pthalocyanine, pteridine, xanthene, acridine, phenoxazine, phenothiazine, phenoxazine, benzofuranopyridine, furanopyridine, benzothiophenopyridine, thiophenopyridine, benzoselenophenopyridine, and selenophenobenzodipyridine; groups containing 2 to 10 ring structures, which can be the same or different types of cyclic aromatic hydrocarbon groups or aromatic heterocyclic groups, and are linked to each other directly or through at least one of the following groups, such as oxygen atom, nitrogen atom, sulfur atom, silicon atom, phosphorus atom, boron atom, chain structural unit, and aliphatic cyclic group.

[0107] In a preferred embodiment, the triplet host material can be selected from compounds containing at least one of the following groups:

[0108]

[0109] X9 is selected from CR 1 R 2 or NR 1 ; Y2 is selected from CR 1 R 2 or NR 1 or O or S; X 1 –X 8 are each independently selected from CR8 or N, and at least one is N, while any two adjacent positions of R 8 may be a single ring or multiple rings, aliphatic or aromatic; R 1 -R 8 have the same meaning as R1, and R 1 -R 8 are the same or different from each other, R 1 -R 8 are the same or different from each other. Any of the groups R 21 , Ar2, and Ar3may form, together with each other and / or the ring to which they are bonded, a single ring or multiple rings, aliphatic or aromatic ring system.

[0110] Examples of suitable triplet host materials are listed below, but are not limited to:

[0111]

[0112]

[0113] 2. Triplet Emitter

[0114] A triplet emitter is also referred to as a phosphorescent emitter. In a preferred embodiment, the triplet emitter is a metal complex of the general formula M(L)n, wherein M is a metal atom, L, which can be the same or different at each occurrence, is an organic ligand which is bonded or coordinated to the metal atom M via one or more positions, and n is an integer greater than 1, preferably selected from 1, 2, 3, 4, 5 or 6. Alternatively, the metal complex is linked to a polymer via one or more positions, preferably via the organic ligand.

[0115] In a preferred embodiment, the metal atom M is selected from transition metals or lanthanides or actinides, preferably selected from Ir, Pt, Pd, Au, Rh, Ru, Os, Sm, Eu, Gd, Tb, Dy, Re, Cu or Ag, and particularly preferred from Os, Ir, Ru, Rh, Re, Pd, Au or Pt.

[0116] Preferably, the triplet emitter comprises a chelating ligand, i.e. a ligand which is coordinated to the metal via at least two binding sites, and particularly preferred the triplet emitter comprises two or three identical or different bidentate or polydentate ligands. Chelating ligands are advantageous for improving the stability of the metal complex.

[0117] Examples of organic ligands can be selected from phenylpyridine derivatives, 7,8- benzochinoline derivatives, 2(2-thienyl)pyridine derivatives, 2(1-naphthyl)pyridine derivatives, or 2 phenylquinoline derivatives. All of these organic ligands can be substituted, for example by fluorine or trifluoromethyl groups. The ancillary ligand can preferably be selected from acetonitrile or picolinic acid.

[0118] In a preferred embodiment, the metal complex which can be used as triplet emitter has the following form:

[0119]

[0120] wherein M is a metal selected from transition metals or lanthanides or actinides, with Ir, Pt, Au being particularly preferred.

[0121] Ar4, which can be the same or different at each occurrence, is a cyclic group which contains at least one donor atom, i.e. an atom with a lone pair of electrons, such as nitrogen or phosphorus, through which the cyclic group is coordinated to the metal; Ar5, which can be the same or different at each occurrence, is a cyclic group which contains at least one C atom, through which the cyclic group is coordinated to the metal; Ar4 and Ar5 are linked together by a covalent bond and can each carry one or more substituents, which can in turn be linked together by substituents; L', which can be the same or different at each occurrence, is a bidentate ancillary ligand, preferably a monanionic bidentate chelating ligand; q1 can be 0, 1, 2 or 3, preferably 2 or 3; q2 can be 0, 1, 2 or 3, preferably 1 or 0.

[0122] Examples of some triplet emitters materials and their applications can be found in the following patent documents and literature: WO200070655, WO 200141512, WO 200202714, WO 200215645, EP 1191613, EP 1191612, EP 1191614, WO 2005033244, WO 2005019373, US 2005 / 0258742, WO 2009146770, WO 2010015307, WO 2010031485, WO 2010054731, WO 2010054728, WO 2010086089, WO 2010099852, WO 2010102709, US 20070087219 Al, US 20090061681 Al, US 20010053462 Al, Baldo, Thompson et al. Nature 403, (2000), 750-753, US 20090061681 Al, US 20090061681 Al, Adachi et al. Appl. Phys. Lett. 78 (2001), 1622-1624, Kido et al. Appl. Phys. Lett. 65 (1994), 2124, Kido et al. Chem. Lett. 657, 1990, US 2007 / 0252517 Al, Johnson et al., JACS 105, 1983, 1795, Wrighton, JACS 96, 1974, 998, Ma et al., Synth. Metals 94, 1998, 245, US 6824895, US 7029766, US 6835469, US 6830828, US 20010053462 Al, WO 2007095118 Al, US 2012004407 Al, WO 2012007088 Al, WO 2012007087 Al, WO 2012007086 Al, US 2008027220 Al, WO 2011157339 Al, CN 102282150 A, WO 2009118087 Al, WO 2013107487 Al, WO 2013094620 Al, WO 2013174471 Al, WO 2014031977 Al, WO 2014112450 Al, WO 2014007565 Al, WO 2014038456 Al, WO 2014024131 Al, WO 2014008982 Al, WO 2014023377 Al.The contents of all of the above-listed patent documents and literature are hereby incorporated by reference in their entirety.

[0123] Some examples of suitable triplet emitters are listed below:

[0124]

[0125]

[0126] 3. TADF materials

[0127] Conventional organic fluorescent materials can only utilize 25% of singlet excitons formed by electric excitation to emit light, and the internal quantum efficiency of the device is low (up to 25%). Although phosphorescent materials can effectively utilize singlet and triplet excitons formed by electric excitation to emit light due to the strong spin-orbital coupling of heavy atom centers to enhance intersystem crossing, the internal quantum efficiency of the device can reach 100%. However, the high cost, poor material stability, and serious efficiency roll-off of phosphorescent materials limit their application in OLEDs. Thermally activated delayed fluorescence (TADF) is the third generation of organic light-emitting materials after organic fluorescent materials and organic phosphorescent materials. This type of material generally has a small singlet-triplet energy level difference (ΔEst), and triplet excitons can be converted into singlet excitons through reverse intersystem crossing to emit light. This can make full use of singlet and triplet excitons formed under electric excitation. The internal quantum efficiency of the device can reach 100%. At the same time, the material structure is controllable, the properties are stable, the price is cheap, and no noble metal is needed, so it has a broad application prospect in the field of OLEDs.

[0128] TADF materials need to have a small singlet-triplet energy level difference, preferably ΔEst<0.3 eV, more preferably ΔEst<0.2 eV, and most preferably ΔEst<0.1 eV. In one preferred embodiment, the TADF material has a small ΔEst, and in another preferred embodiment, the TADF has a high fluorescence quantum efficiency. Some TADF emitting materials can be found in the following patent documents: CN103483332(A), TW201309696(A), TW201309778(A), TW201343874(A), TW201350558(A), US20120217869(A1), WO2013133359(A1), WO2013154064(A1), Adachi, et. al. Adv. Mater., 21, 2009, 4802, Adachi, et. al. Appl. Phys. Lett., 98, 2011, 083302, Adachi, et. al. Appl. Phys. Lett., 101, 2012, 093306, Adachi, et. al. Chem. Commun., 48, 2012, 11392, Adachi, et. al. Nature Photonics, 6, 2012, 253, Adachi, et. al. Nature, 492, 2012, 234, Adachi, et. al. J. Am. Chem. Soc, 134, 2012, 14706, Adachi, et. al. Angew. Chem. Int. Ed, 51, 2012, 11311, Adachi, et. al. Chem. Commun., 48, 2012, 9580, Adachi, et. al. Chem. Commun., 48, 2013, 10385, Adachi, et. al. Adv. Mater., 25, 2013, 3319, Adachi, et. al. Adv. Mater., 25, 2013, 3707, Adachi, et. al. Chem. Mater., 25, 2013, 3038, Adachi, et. al. Chem. Mater., 25, 2013, 3766, Adachi, et. al. J. Mater. Chem. C., 1, 2013, 4599, Adachi, et. al. J. Phys. Chem. A., 117, 2013, 5607, the contents of all of the above listed patent or article documents are hereby incorporated by reference in their entirety.

[0129] Some examples of suitable TADF emitting materials are listed below:

[0130]

[0131]

[0132] The present application also relates to a composition comprising at least one compound or polymer or mixture as described above, and at least one organic solvent; said at least one organic solvent being selected from aromatic or heteroaromatic, ester, aromatic ketone or aromatic ether, aliphatic ketone or aliphatic ether, alicyclic or olefinic compound, or borate or phosphate ester compound, or a mixture of two or more solvents.

[0133] In a preferred embodiment, a composition according to the present application, said at least one organic solvent is selected from aromatic or heteroaromatic based solvents.

[0134] Examples of aromatic or heteroaromatic based solvents suitable for the present application are, but are not limited to: p-diisopropylbenzene, amylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-cymene, diamylbenzene, triamylbenzene, pentyltoluene, 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, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, p-cymene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorobenzophenone, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorobenzhydrol, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropyl naphthalene, quinoline, isoquinoline, 2-furoic acid methyl ester, 2-furoic acid ethyl ester, and the like;

[0135] Examples of aromatic ketone based solvents suitable for the present application are, but are not limited to: 1-tetralone, 2-tetralone, 2-(phenyloxy)tetralone, 6-(methyloxy)tetralone, acetophenone, propiophenone, benzophenone, and their derivatives such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, and the like;

[0136] Examples of aromatic ether based solvents suitable for use in the present application include, but are not limited to, 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethyl ethyl ether, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butyl anisole, trans-p-allylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxy methyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether;

[0137] In some preferred embodiments, the at least one organic solvent of the composition according to the present application can be selected from the group consisting of aliphatic ketones, such as, for example, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, p-methylacetophenone, isophorone, di-n-pentyl ketone, and the like; or aliphatic ethers, such as, for example, 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, and the like.

[0138] In other preferred embodiments, the at least one organic solvent of the composition according to the present application can be selected from the group consisting of ester based solvents: octanoic acid alkyl ester, sebacic acid alkyl ester, stearic acid alkyl ester, benzoic acid alkyl ester, phenylacetic acid alkyl ester, cinnamic acid alkyl ester, oxalic acid alkyl ester, maleic acid alkyl ester, alkyl lactone, oleic acid alkyl ester, and the like. Particularly preferred are octanoic acid octyl ester, sebacic acid diethyl ester, diallyl phthalate, isononyl isononanoate.

[0139] The solvent can be used alone or as a mixture of two or more organic solvents.

[0140] In certain preferred embodiments, a composition according to the present application comprises at least one organic compound or polymer or mixture as described above and at least one organic solvent, and can further comprise another organic solvent. Examples of another organic solvent include, but are not limited to, methanol, ethanol, 2-methoxyethanol, dichloromethane, trichloromethane, 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, tetrahydronaphthalene, decalin, indene, and / or mixtures thereof.

[0141] In some preferred embodiments, solvents particularly suitable for the present application are solvents having Hansen solubility parameters in the following ranges:

[0142] δd (dispersion force) in the range of 17.0 to 23.2 MPa1 / 2, especially in the range of 18.5 to 21.0 MPa1 / 2;

[0143] δp (polar force) in the range of 0.2 to 12.5 MPa1 / 2, especially in the range of 2.0 to 6.0 MPa1 / 2;

[0144] δh (hydrogen bond force) in the range of 0.9 to 14.2 MPa1 / 2, especially in the range of 2.0 to 6.0 MPa1 / 2.

[0145] The organic solvent according to the present application is selected taking into account its boiling point parameter. In the present application, the organic solvent has a boiling point of > 150 °C; preferably of > 180 °C; more preferably of > 200 °C; even more preferably of > 250 °C; most preferably of > 275 °C or > 300 °C. A boiling point in these ranges is beneficial to prevent clogging of the nozzles of the inkjet printing head. The organic solvent can evaporate from the solvent system to form a thin film comprising the functional material.

[0146] In a preferred embodiment, the composition according to the present application is a solution.

[0147] In another preferred embodiment, the composition according to the present application is a suspension.

[0148] The composition according to the present application can comprise from 0.01 to 10 wt.-%, preferably from 0.1 to 15 wt.-%, more preferably from 0.2 to 5 wt.-%, most preferably from 0.25 to 3 wt.-%, of the compound or mixture according to the present application.

[0149] The present application also relates to the use of the composition as a coating material or printing ink in the production of organic electronic devices, particularly preferably by a printing or coating process.

[0150] 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, offset lithography printing, flexographic printing, rotogravure printing, spray coating, brush coating or pad printing, slit- coating, and the like. Preferred are gravure printing, nozzle printing and inkjet printing. The solution or suspension can additionally comprise one or more components, such as surface-active compounds, lubricating agents, wetting agents, dispersing agents, hydrophobic agents, adhesive agents and the like, for example for adjusting the viscosity, the filming properties, the adhesion, etc. With regard to the printing techniques, and the related requirements for the respective solutions, such as solvents and concentrations, viscosities, etc.

[0151] The present application further provides the use of an organic compound, polymer, mixture or composition as described above in an organic electronic device, which can be, but is not limited to, an organic light emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light emitting electrochemical cell (OLEEC), an organic field effect transistor (OFET), an organic light emitting field effect transistor, an organic laser, an organic spintronic device, a photodiode, an organic sensor and an organic plasmon emitting diode, and is particularly preferred to be an OLED. In the present application, the compound is preferably used in the hole transport layer of an OLED device.

[0152] The present application further relates to an organic electronic device comprising at least one functional layer, which comprises at least one organic compound, polymer, mixture or composition as described above. Further, the organic electronic device comprises a cathode, an anode and at least one functional layer, which comprises at least one compound or mixture or composition as described above. The functional layer is selected from the group consisting of a hole injection layer (HIL), a hole transport layer (HTL), an emitting layer (EML), an electron blocking layer (EBL), an electron injection layer (EIL), an electron transport layer (ETL), a hole blocking layer (HBL); preferably, the functional layer is selected from the group consisting of a hole transport layer.

[0153] The organic electronic device can be, but is not limited to, an organic light emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light emitting electrochemical cell (OLEEC), an organic field effect transistor (OFET), an organic light emitting field effect transistor, an organic laser, an organic spintronic device, a photodiode, an organic sensor and an organic plasmon emitting diode, and is particularly preferred to be an organic electroluminescent device, such as an OLED, an OLEEC, an organic light emitting field effect transistor.

[0154] In the light emitting devices described above, particularly OLEDs, a substrate, an anode, at least one light emitting layer, and a cathode are included.

[0155] The substrate can be opaque or transparent. A transparent substrate can be used to make a transparent light emitting device. See, for example, Bulovic et al., Nature 1996, 380, p29, and Gu et al., Appl. Phys. Lett. 1996, 68, p2606. The substrate can be rigid or flexible. The substrate can be plastic, metal, semiconductor wafer, or glass. Preferably, the substrate has a smooth surface. Substrates without surface defects are particularly desirable. In a preferred embodiment, the substrate is flexible, and is selected from the group consisting of polymeric films or plastics having a glass transition temperature Tg of 150°C or greater, preferably greater than 200°C, more preferably greater than 250°C, and most preferably greater than 300°C. Examples of suitable flexible substrates include poly(ethylene terephthalate) (PET) and polyethylene naphthalate (PEN).

[0156] The anode can include a conductive metal or metal oxide, or a conductive polymer. The anode can readily inject holes into a hole injection layer (HIL) or a hole transport layer (HTL) or a light emitting layer. In a preferred embodiment, the absolute value of the difference between the work function of the anode and the HOMO level or valence band level of the light emitter in the light emitting layer or the p-type semiconductor material used as a HIL or HTL 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. Examples of anode materials include, but are not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), and the like. Other suitable anode materials are known and can be readily selected by one of ordinary skill in the art. The anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, e-beam, and the like. In certain embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to make devices according to the present application.

[0157] The cathode can comprise a conductive metal or metal oxide. The cathode can readily inject electrons into the EIL or ETL or directly into the light-emitting layer. In a preferred embodiment, the absolute value of the difference between the work function of the cathode and the LUMO level or conduction band level of the light emitter in the light-emitting layer or of the n-type semiconductor material as electron injection layer (EIL) or electron transport layer (ETL) or hole blocking layer (HBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials that can be used as cathode of an OLED can be used as cathode material of the inventive device. Examples of cathode materials include, but are not limited to, Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, and the like. The cathode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, e-beam, and the like.

[0158] The OLED can also comprise other functional layers, such as a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an electron injection layer (EIL), an electron transport layer (ETL), a hole blocking layer (HBL). Suitable materials for use in these functional layers are described in detail above and in WO2010135519A1, US20090134784A1 and WO2011110277A1, the entire contents of which are hereby incorporated by reference.

[0159] The light-emitting device according to the present application has a light emission wavelength between 300 and 1200 nm, preferably between 350 and 1000 nm, and more preferably between 400 and 900 nm.

[0160] The present application also relates to the use of the electroluminescent device according to the present application in various electronic devices, including, but not limited to, display devices, lighting devices, light sources, sensors, and the like.

[0161] The present application will be described in connection with preferred embodiments. However, it will be understood that the application is not limited to the described embodiments, but can admit to several modifications and embodiments within the scope of the present application as broadly recorded in the claims. The skilled person will realize that certain changes can be made to the embodiments described and that such changes are to be understood as within the scope of the present application. DETAILED EMBODIMENTS

[0163] 1. Synthesis of compounds

[0164] Example 1

[0165]

[0166] Under nitrogen atmosphere, reactant A (30.8 g, 100.0 mmol), pinacol diboronic acid (38.1 g, 150 mmol), [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride (3.7 g, 5 mmol) and potassium acetate (14.7 g, 150 mmol) were sequentially added into a 1000 mL three-necked flask, and then 500 mL of 1,4-dioxane was injected into the flask. The reaction mixture was stirred at room temperature, and then the solvent was refluxed by heating, and the reflux reaction was maintained for 10 hours. After the reaction was completed, the reaction system was cooled to room temperature, and the solvent was removed by rotary evaporation. The reaction mixture was extracted with dichloromethane and saturated sodium chloride solution, and the combined organic phase was dried, filtered and concentrated to obtain product 1a about 29.8 g with a yield of 87%. MS (ASAP) = 356.2.

[0167] Under nitrogen atmosphere, intermediate 1a (29.0 g, 81.4 mmol), cyanuric chloride (7.5 g, 40.7 mmol), potassium carbonate (16.9 g, 122.1 mmol) and tetrakis(triphenylphosphine)palladium (2.3 g, 2 mmol) were sequentially added into a 1000 mL three-necked flask, and then 400 mL of 1,4-dioxane and 50 mL of deionized water were sequentially injected into the flask. The reaction mixture was stirred at room temperature, and then the solvent was refluxed by heating, and the reflux reaction was maintained for 8 hours. After the reaction was completed, the reaction system was cooled to room temperature, extracted with ethyl acetate, and the combined organic phase was dried, filtered and concentrated. The product 1b was separated by silica gel column chromatography using dichloromethane:n-hexane = 1:3 (volume ratio) as the eluent to obtain about 27 g of product 1b with a yield of 74%. MS (ASAP) = 571.2.

[0168] Under anhydrous and anaerobic conditions, C (13.3 g, 50 mmol) was added into a 500 mL three-necked flask, and then 200 mL of anhydrous tetrahydrofuran was injected into the flask, and stirred at -78°C. Then, n-butyl lithium-n-hexane solution (25 mL, 75 mmol) was slowly added into the reaction system, and stirred at -78°C for 2 hours. Then, reactant B (10 g, 100 mmol) was dissolved in 100 mL of anhydrous tetrahydrofuran, and injected into the reaction system, and stirred at -78°C for 2 hours, and then gradually warmed to room temperature, and continued to stir for 12 hours. Finally, deionized water was added to quench the reaction, and the solvent was removed. The resulting product was dissolved in a mixture of concentrated hydrochloric acid / glacial acetic acid (50 mL / 200 mL) under nitrogen atmosphere, and refluxed at 110°C for 8 hours. After the reaction was completed, the reaction mixture was separated and dried. The crude product was purified by column chromatography using dichloromethane: petroleum ether = 1:8 (volume ratio) as the eluent to obtain about 12.1 g of crude product 1c with a yield of about 86%. MS (ASAP) = 280.1.

[0169] Under nitrogen atmosphere, intermediate 1c (12 g, 42.8 mmol), bis(pinacolato)diboron (13 g, 51.4 mmol), [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride (1.6 g, 2.1 mmol) and potassium acetate (6.3 g, 64.2 mmol) were added into a 500 mL three-necked flask in turn, then 300 mL of 1,4-dioxane was injected into the flask. The reaction mixture was stirred at room temperature, then the solvent was refluxed by heating, and the reaction was kept for 9 hours. After the reaction was completed, the solvent was removed by rotary evaporation, and the obtained crude product was purified by column chromatography using dichloromethane: petroleum ether = 1:2 (volume ratio) as eluent to obtain product 1d about 11.8 g with a yield of 74%. MS (ASAP) = 372.3.

[0170] Under nitrogen atmosphere, intermediate 1b (21.3 g, 37.3 mmol), intermediate 1d (11.6 g, 31.1 mmol), potassium carbonate (6.4 g, 46.7 mmol), tetrakis(triphenylphosphine)palladium (1.8 g, 1.6 mmol) and 2-dicyclohexylphosphino-2,4,6-triisopropylbiphenyl (1.5 g, 3.2 mmol) were added into a 1000 mL three-necked flask in turn, then 400 mL of 1,4-dioxane and 50 mL of deionized water were injected into the flask in turn. The reaction mixture was stirred at room temperature, then the solvent was refluxed by heating, and the reaction was kept for 12 hours. After the reaction was completed, the solvent was removed by rotary evaporation, the organic phase was extracted with ethyl acetate, combined and dried, filtered and concentrated, then the product was separated by silica gel chromatography column using ethyl acetate: n-hexane = 1:10 (volume ratio) as eluent to obtain product (1) about 15 g with a yield of 62%. MS (ASAP) = 781.3.

[0171] Example 2

[0172]

[0173] In an anhydrous and anaerobic environment, D (26.6 g, 100 mmol) was added to a 1000 mL three-necked flask, then 300 mL of anhydrous tetrahydrofuran was injected into the flask, stirred at -78°C, then n-butyllithium-n-hexane solution (50 mL, 150 mmol) was slowly added dropwise into the reaction system, then continued to stir at -78°C for 3 hours. Then, the reactant B (20 g, 200 mmol) was dissolved in 150 mL of anhydrous tetrahydrofuran, injected into the reaction system, stirred at -78°C for 2 hours, then gradually increased to room temperature, and continued to stir for 12 hours. Finally, deionized water was added to quench the reaction, the solvent was removed, and the resulting product was dissolved in a mixture of concentrated hydrochloric acid / glacial acetic acid (50 mL / 200 mL) under a nitrogen atmosphere, and refluxed at 110°C for 8 hours. After the reaction was completed, the liquid was separated and dried, and the resulting crude product was purified by column chromatography using dichloromethane: petroleum ether = 1:8 (volume ratio) as the eluent to obtain about 23 g of crude product 2a, with a yield of about 82%. MS (ASAP) = 280.1.

[0174] Under a nitrogen atmosphere, the reactant E (46.3 g, 100 mmol), pinacol diboronic acid (30.5 g, 120 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (2.9 g, 4 mmol), and potassium acetate (14.7 g, 150 mmol) were sequentially added to a 1000 mL three-necked flask, then 650 mL of 1,4-dioxane was injected into the flask. The reaction mixture was stirred at room temperature, then the solvent was refluxed by heating, and the reflux reaction was maintained for 12 hours. After the reaction was completed, it was cooled to room temperature, the solvent in the reaction system was removed by rotary evaporation, and the resulting crude product was purified by column chromatography using dichloromethane: petroleum ether = 1:2 (volume ratio) as the eluent to obtain about 43.2 g of product 2b, with a yield of 84%. MS (ASAP) = 511.2.

[0175] Under a nitrogen atmosphere, the intermediate 2a (20 g, 71.4 mmol), intermediate 2b (40.1 g, 78.5 mmol), potassium carbonate (14.8 g, 107.1 mmol), tetrakis(triphenylphosphine)palladium (4.1 g, 3.57 mmol), and 2-dicyclohexylphosphine-2,4,6-triisopropylbiphenyl (3.4 g, 7.14 mmol) were sequentially added to a 1000 mL three-necked flask, then 500 mL of 1,4-dioxane and 100 mL of deionized water were sequentially injected into the flask. The reaction mixture was stirred at room temperature, then the solvent was refluxed by heating, and the reflux reaction was maintained for 18 hours. After the reaction was completed, it was cooled to room temperature, extracted with ethyl acetate, the organic phases were combined, dried, filtered, and concentrated, and the product was separated by silica gel chromatography using ethyl acetate:n-hexane = 1:8 (volume ratio) as the eluent to obtain about 32 g of product (2) with a yield of 71%. MS (ASAP) = 628.3.

[0176] Example 3

[0177]

[0178] Under nitrogen atmosphere, reactant F (30.1 g, 100 mmol), pinacol diboronic acid (30.5 g, 120 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (2.9 g, 4 mmol) and potassium acetate (14.7 g, 150 mmol) were sequentially added into a 1000 mL three-necked flask, then 500 mL 1,4-dioxane was injected into the flask. The reaction mixture was stirred at room temperature, then the solvent was refluxed by heating, and the reflux reaction was kept for 12 hours. After the reaction was completed, it was cooled to room temperature, and the solvent in the reaction system was removed by rotary evaporation. The obtained crude product was purified by column chromatography using dichloromethane: petroleum ether = 1:3 (volume ratio) as the eluent to obtain product 3a about 27.1 g with a yield of 76%. MS (ASAP) = 358.1.

[0179] Under nitrogen atmosphere, reactant G (24.3 g, 62.8 mmol), potassium carbonate (10.4 g, 75.4 mmol), tetrakis(triphenylphosphine)palladium (2.2 g, 1.9 mmol) and 2-dicyclohexylphosphino-2,4,6-triisopropylbiphenyl (1.8 g, 3.8 mmol) were sequentially added into a 1000 mL three-necked flask, then 300 mL 1,4-dioxane and 100 mL deionized water were sequentially injected into the flask, then intermediate 3a (27 g, 75.4 mmol) was dissolved in 200 mL 1,4-dioxane and slowly added into the reaction system and the solvent was refluxed by heating, and the reflux reaction was kept for 12 hours. After the reaction was completed, it was cooled to room temperature, extracted with ethyl acetate, and the organic phases were combined, dried, filtered and concentrated. The product 3b was obtained by silica gel chromatography column separation using ethyl acetate: n-hexane = 1:10 (volume ratio) as the eluent, about 23.4 g with a yield of 70%. MS (ASAP) = 539.1.

[0180] Under nitrogen atmosphere, intermediate 3b (23 g, 42.7 mmol), pinacol diboronic acid (16.2 g, 64 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (1.5 g, 2.1 mmol) and potassium acetate (6.3 g, 64 mmol) were sequentially added into a 1000 mL three-necked flask, then 500 mL 1,4-dioxane was injected into the flask. The reaction mixture was stirred at room temperature, then the solvent was refluxed by heating, and the reflux reaction was kept for 12 hours. After the reaction was completed, it was cooled to room temperature, and the solvent in the reaction system was removed by rotary evaporation. The obtained crude product was purified by column chromatography using dichloromethane: petroleum ether = 1:2 (volume ratio) as the eluent to obtain product 3c about 16.6 g with a yield of 66%. MS (ASAP) = 587.3.

[0181] Under nitrogen atmosphere, intermediate 3c (16.5 g, 28.1 mmol), intermediate 2a (6.6 g, 23.4 mmol), potassium carbonate (4.8 g, 35.1 mmol), tetrakis triphenylphosphine palladium (1.4 g, 1.2 mmol) and 2-dicyclohexylphosphino-2,4,6-triisopropylbiphenyl (1.1 g, 2.4 mmol) were added into a 500 mL three-necked flask in turn, then 200 mL 1,4-dioxane and 40 mL deionized water were added into the flask in turn. The reaction mixture was stirred at room temperature, then the solvent was refluxed by heating, and the reflux reaction was kept for 10 hours. After the reaction was completed, it was cooled to room temperature, extracted with ethyl acetate, and the organic phase was combined, dried, filtered and concentrated. The product (3) was separated by silica gel column chromatography using dichloromethane:n-hexane = 1:5 (volume ratio) as eluent, and about 11.4 g of product was obtained with a yield of 69%. MS (ASAP) = 705.3.

[0182] Example 4

[0183]

[0184] Under nitrogen atmosphere, reactant H (33.2 g, 100 mmol), potassium carbonate (20.7 g, 150 mmol) and tetrakis triphenylphosphine palladium (3.5 g, 3 mmol) were added into a 1000 mL three-necked flask in turn, then 300 mL 1,4-dioxane and 100 mL deionized water were added into the flask in turn. Then a solution of reactant I (25.5 g, 110 mmol) in 1,4-dioxane was added dropwise into the reaction system, the solvent was refluxed by heating, and the reflux reaction was kept for 18 hours. After the reaction was completed, it was cooled to room temperature, extracted with ethyl acetate, and the organic phase was combined, dried, filtered and concentrated. The product 4a was separated by silica gel column chromatography using dichloromethane:n-hexane = 1:10 (volume ratio) as eluent, and about 29.4 g of product was obtained with a yield of 75%. MS (ASAP) = 392.0.

[0185] Under anhydrous and anaerobic condition, intermediate 4a (29.2 g, 74.5 mmol) was added into a 1000 mL three-necked flask, then 300 mL of anhydrous tetrahydrofuran was injected into the flask, stirred at -78 °C, then n-butyllithium-n-hexane solution (37 mL, 117 mmol) was slowly added into the reaction system, then continued to stir at -78 °C for 3 hours. Then, the reactant B (20 g, 117 mmol) was dissolved in 150 mL of anhydrous tetrahydrofuran, injected into the reaction system, stirred at -78 °C for 2 hours, then gradually increased to room temperature, continued to stir for 12 hours. Finally, deionized water was added into the reaction system to quench, removed the solvent, the obtained product was dissolved in concentrated hydrochloric acid / glacial acetic acid mixture (75 mL / 300 mL) under nitrogen atmosphere, and refluxed at 110 °C for 8 hours. After the reaction was completed, the liquid was separated and dried, and the obtained crude product was purified by column chromatography using dichloromethane: petroleum ether = 1:5 (volume ratio) as the eluent to obtain the crude product 4b about 26 g, with a yield of about 86%. MS (ASAP) = 406.2.

[0186] Under nitrogen atmosphere, the reactant J (38.7 g, 100 mmol), bis(pinacolato)diboron (38.1 g, 150 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (3.67 g, 5 mmol) and potassium acetate (14.7 g, 150 mmol) were sequentially added into a 1000 mL three-necked flask, then 600 mL of 1,4-dioxane was injected into the flask. The reaction mixture was stirred at room temperature, then the solvent was refluxed by heating, and the reflux reaction was maintained for 15 hours. After the reaction was completed, it was cooled to room temperature, the solvent in the reaction system was removed by rotary evaporation, and the obtained crude product was purified by column chromatography using dichloromethane: petroleum ether = 1:2 (volume ratio) as the eluent to obtain the product 4c about 39.6 g, with a yield of 91%. MS (ASAP) = 435.2.

[0187] Under nitrogen atmosphere, the intermediate 4c (30 g, 68.9 mmol), intermediate 4b (25 g, 57.4 mmol), potassium carbonate (11.9 g, 86.1 mmol), tetrakis(triphenylphosphine)palladium (3.3 g, 2.87 mmol) and 2-dicyclohexylphosphino-2,4,6-triisopropylbiphenyl (2.7 g, 5.7 mmol) were sequentially added into a 1000 mL three-necked flask, then 500 mL of 1,4-dioxane and 100 mL of deionized water were sequentially injected into the flask. The reaction mixture was stirred at room temperature, then the solvent was refluxed by heating, and the reflux reaction was maintained for 12 hours. After the reaction was completed, it was cooled to room temperature, extracted with ethyl acetate, the organic phases were combined, dried, filtered and concentrated, and the product (4) was separated by silica gel chromatography column using dichloromethane: n-hexane = 1:3 (volume ratio) as the eluent to obtain about 28.1 g, with a yield of 72%. MS (ASAP) = 679.3.

[0188] Example 5

[0189]

[0190] The reactants K (23.2 g, 100 mmol), pinacol diboronic acid (38.1 g, 150 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (3.67 g, 5 mmol) and potassium acetate (14.7 g, 150 mmol) were sequentially added to a 500 mL three-necked flask under a nitrogen atmosphere, and then 300 mL of 1,4-dioxane was injected into the flask. The reaction mixture was stirred at room temperature, and then the solvent was brought to reflux by heating, and the reflux reaction was maintained for 5 hours. After the reaction was completed, the reaction system was cooled to room temperature, and the solvent was removed by rotary evaporation. The obtained crude product was purified by column chromatography using dichloromethane: petroleum ether = 1:4 (volume ratio) as the eluent to obtain product 5a about 21.8 g, with a yield of 94%. MS (ASAP) = 232.

[0191] The reactants L (21.9 g, 97.3 mmol), intermediate 5a (21.5 g, 92.7 mmol), potassium carbonate (15.4 g, 111.2 mmol) and tetrakis(triphenylphosphine)palladium (3.2 g, 2.78 mmol) were sequentially added to a 1000 mL three-necked flask under a nitrogen atmosphere, and then 600 mL of tetrahydrofuran and 150 mL of deionized water were sequentially injected into the flask. The reaction mixture was stirred at room temperature, and then the solvent was brought to reflux by heating, and the reflux reaction was maintained for 18 hours. After the reaction was completed, the reaction system was cooled to room temperature, extracted with ethyl acetate, and the combined organic phase was dried, filtered and concentrated. The product 5b was obtained by silica gel column chromatography using ethyl acetate: n-hexane = 1:10 (volume ratio) as the eluent, about 20.7 g, with a yield of 65%. MS (ASAP) = 343.1.

[0192] ​In an anhydrous and anaerobic environment, the reactant M (26.7 g, 100 mmol) was added into a 1000 mL three-necked flask, then 300 mL of anhydrous tetrahydrofuran was injected into the flask, stirred at -78°C, then the n-butyllithium-n-hexane solution (40 mL, 120 mmol) was slowly added into the reaction system, then continued to stir for 3 hours at -78°C. Then, the reactant B (20 g, 120 mmol) was dissolved in 150 mL of anhydrous tetrahydrofuran, injected into the reaction system, stirred for 2 hours at -78°C, then gradually increased to room temperature, continued to stir for 12 hours. Finally, deionized water was added to quench the reaction, the solvent was removed, and the resulting product was dissolved in a mixture of concentrated hydrochloric acid / glacial acetic acid (75 mL / 300 mL) under a nitrogen atmosphere, and refluxed at 110°C for 8 hours. After the reaction was completed, the liquid was separated and dried, and the resulting crude product was purified by column chromatography using dichloromethane: petroleum ether = 1:5 (volume ratio) as the eluent to obtain about 20.1 g of the crude product 5c, with a yield of about 71.8%. MS (ASAP) = 280.1.

[0193] Under a nitrogen atmosphere, intermediate 5c (20 g, 71.4 mmol), bis(pinacolato)diboron (27.2 g, 107 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (3.57 g, 5 mmol) and potassium acetate (10.5 g, 107.1 mmol) were sequentially added into a 500 mL three-necked flask, then 300 mL of 1,4-dioxane was injected into the flask. The reaction mixture was stirred at room temperature, then the solvent was refluxed by heating, and the reflux reaction was maintained for 12 hours. After the reaction was completed, the temperature was cooled to room temperature, the solvent in the reaction system was removed by rotary evaporation, and the resulting crude product was purified by column chromatography using dichloromethane: petroleum ether = 1:3 (volume ratio) as the eluent to obtain about 22.6 g of the product 5d, with a yield of 85%. MS (ASAP) = 372.2.

[0194] Under a nitrogen atmosphere, intermediate 5d (26 g, 70 mmol), intermediate 5b (20 g, 58.3 mmol), potassium carbonate (12.1 g, 87.5 mmol), tetrakis(triphenylphosphine)palladium (3.4 g, 2.9 mmol) and 2-dicyclohexylphosphino-2,4,6-triisopropylbiphenyl (2.8 g, 5.8 mmol) were sequentially added into a 500 mL three-necked flask, then 300 mL of 1,4-dioxane and 80 mL of deionized water were sequentially injected into the flask. The reaction mixture was stirred at room temperature, then the solvent was refluxed by heating, and the reflux reaction was maintained for 14 hours. After the reaction was completed, the temperature was cooled to room temperature, extracted with ethyl acetate, the organic phases were combined, dried, filtered and concentrated, and the product (5) was separated by silica gel chromatography column using dichloromethane: n-hexane = 1:2 (volume ratio) as the eluent to obtain about 28.1 g of the product, with a yield of 72%. MS (ASAP) = 553.3.

[0195] Example 6

[0196]

[0197] The reactant N (26.7 g, 100 mmol) was added into a 1000 mL three-necked flask under anhydrous and anaerobic environment, then 300 mL of anhydrous tetrahydrofuran was injected into the flask, and stirred at -78 °C, then n-butyllithium-n-hexane solution (40 mL, 120 mmol) was slowly added into the reaction system, and then continued to stir at -78 °C for 3 hours. Then, the reactant B (20 g, 120 mmol) was dissolved in 150 mL of anhydrous tetrahydrofuran, and injected into the reaction system, and stirred at -78 °C for 2 hours, then gradually increased to room temperature, and continued to stir for 12 hours. Finally, deionized water was added into the reaction system to quench, and the solvent was removed, and the obtained product was dissolved in a mixture of concentrated hydrochloric acid / glacial acetic acid (75 mL / 300 mL) under a nitrogen atmosphere, and refluxed at 110 °C for 8 hours. After the reaction was completed, the reaction mixture was separated and dried, and the obtained crude product was purified by column chromatography using dichloromethane: petroleum ether = 1:8 (volume ratio) as the eluent to obtain the crude product 6a about 21.3 g, with a yield of about 76%. MS (ASAP) = 280.1.

[0198] The reactant O (38.7 g, 100 mmol), bis(pinacolato)diboron (38.1 g, 150 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (3.57 g, 5 mmol) and potassium acetate (14.7 g, 150 mmol) were sequentially added into a 1000 mL three-necked flask under a nitrogen atmosphere, then 400 mL of 1,4-dioxane was injected into the flask. The reaction mixture was stirred at room temperature, then the solvent was refluxed by increasing the temperature, and the reflux reaction was maintained for 16 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the solvent in the reaction system was removed by rotary evaporation, and the obtained crude product was purified by column chromatography using dichloromethane: petroleum ether = 1:3 (volume ratio) as the eluent to obtain the product 6b about 35.7 g, with a yield of 82%. MS (ASAP) = 435.2.

[0199] Under nitrogen atmosphere, intermediate 6b (35.5 g, 85.6 mmol), intermediate 6a (20 g, 71.3 mmol), potassium carbonate (12.1 g, 107 mmol), tetrakis triphenyl phosphine palladium (4.2 g, 3.6 mmol) and 2-dicyclohexylphosphino-2,4,6-triisopropylbiphenyl (3.4 g, 7.2 mmol) were added into a 1000 mL three-necked flask in sequence, then 600 mL 1,4-dioxane and 100 mL deionized water were added into the flask in sequence. The reaction mixture was stirred at room temperature, then the solvent was refluxed by heating, and the reflux reaction was kept for 14 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, extracted with ethyl acetate, and the organic phase was combined, dried, filtered and concentrated. The product (6) was obtained by silica gel column chromatography using dichloromethane: n-hexane = 1:2 (volume ratio) as eluent, about 31 g, yield 78%. MS (ASAP) = 553.3.

[0200] Example 7

[0201]

[0202] Under anhydrous and anaerobic environment, the reactant P (26.7 g, 100 mmol) was added into a 1000 mL three-necked flask, then 300 mL anhydrous tetrahydrofuran was added into the flask, stirred at -78°C, then n-butyl lithium-n-hexane solution (40 mL, 120 mmol) was slowly added into the reaction system, then continued to stir at -78°C for 3 hours. Then, the reactant B (20 g, 120 mmol) was dissolved in 150 mL anhydrous tetrahydrofuran, and was added into the reaction system, stirred at -78°C for 2 hours, then gradually increased to room temperature, and continued to stir for 12 hours. Finally, deionized water was added into the reaction system to quench, the solvent was removed, and the obtained product was dissolved in concentrated hydrochloric acid / glacial acetic acid mixture (75 mL / 300 mL) under nitrogen atmosphere, and refluxed at 110°C for 8 hours. After the reaction was completed, the reaction mixture was separated and dried, and the obtained crude product was purified by column chromatography using dichloromethane: petroleum ether = 1:8 (volume ratio) as eluent to obtain the crude product 7a, about 22.7 g, yield about 81%. MS (ASAP) = 280.1.

[0203] Under nitrogen atmosphere, intermediate 7a (22.5 g, 80.3 mmol), potassium carbonate (16.6 g, 120.5) and tetrakis triphenyl phosphine palladium (2.8 g, 2.4 mmol) were added into a 500 mL three-necked flask in sequence, then 200 mL of toluene and 80 mL of deionized water were added into the flask in sequence, then a solution of reactant Q (19.3 g, 96.4 mmol) in toluene was added into the reaction system drop by drop. Then the solvent was refluxed by heating, and the reaction was kept for 8 hours. After the reaction was completed, the reaction system was cooled to room temperature, extracted with ethyl acetate, and the organic phase was combined, dried, filtered and concentrated. The product 7b was separated by silica gel column chromatography using dichloromethane: n-hexane = 1:8 (volume ratio) as the eluent, and about 26.7 g of the product 7b was obtained with a yield of 83%. MS (ASAP) = 400.1.

[0204] Under nitrogen atmosphere, reactant R (38.7 g, 100 mmol), bis(pinacolato)diboron (38.1 g, 150 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (3.57 g, 5 mmol) and potassium acetate (14.7 g, 150 mmol) were added into a 1000 mL three-necked flask in sequence, then 600 mL of 1,4-dioxane was added into the flask. The reaction mixture was stirred at room temperature, then the solvent was refluxed by heating, and the reaction was kept for 12 hours. After the reaction was completed, the reaction system was cooled to room temperature, and the solvent was removed by rotary evaporation. The obtained crude product was purified by column chromatography using dichloromethane: petroleum ether = 1:2 (volume ratio) as the eluent, and about 37.7 g of the product 7c was obtained with a yield of 87%. MS (ASAP) = 435.2.

[0205] Under nitrogen atmosphere, intermediate 7b (26.5 g, 66.3 mmol), intermediate 7c (34.6 g, 79.6 mmol), potassium carbonate (13.7 g, 99.5 mmol), tetrakis triphenyl phosphine palladium (3.8 g, 3.3 mmol) and 2-dicyclohexylphosphino-2,4,6-triisopropylbiphenyl (3.1 g, 6.6 mmol) were added into a 1000 mL three-necked flask in sequence, then 500 mL of 1,4-dioxane and 100 mL of deionized water were added into the flask. The reaction mixture was stirred at room temperature, then the solvent was refluxed by heating, and the reaction was kept for 14 hours. After the reaction was completed, the reaction system was cooled to room temperature, extracted with ethyl acetate, and the organic phase was combined, dried, filtered and concentrated. The product (7) was separated by silica gel column chromatography using dichloromethane: n-hexane = 1:4 (volume ratio) as the eluent, and about 31.3 g of the product (7) was obtained with a yield of 75%. MS (ASAP) = 629.3.

[0206] Example 8

[0207]

[0208] Under nitrogen atmosphere, the reactant S (40 g, 161.3 mmol) was dissolved in a 1000 mL three-necked flask with 400 mL dichloromethane, 50 mL triethylamine was added, and the reaction solution was cooled to 0°C with an ice water bath. Then, 45 mL trifluoromethanesulfonic anhydride was slowly added dropwise into the reaction solution. After the reaction was completed, the reaction mixture was poured into 1000 mL deionized water, extracted with ethyl acetate, and the combined organic phase was dried, filtered and concentrated. The product 8a was separated by silica gel column chromatography with dichloromethane: n-hexane = 1:4 (volume ratio) as eluent to obtain about 55.2 g of product 8a with a yield of about 90%. MS (ASAP) = 379.9.

[0209] Under nitrogen atmosphere, the intermediate 8a (50 g, 131.6 mmol), the reactant T (29.4 g, 131.6 mmol), potassium carbonate (21.8 g, 157.9) and tetrakis triphenylphosphine palladium (4.6 g, 3.9 mmol) were sequentially added to a 1000 mL three-necked flask, and then 500 mL 1,4-dioxane and 100 mL deionized water were sequentially injected into the flask. The reaction mixture was stirred at room temperature, then the solvent was refluxed by heating, and the reflux reaction was maintained for 12 hours. After the reaction was completed, the reaction solution was cooled to room temperature, extracted with ethyl acetate, and the combined organic phase was dried, filtered and concentrated. The product 8b was separated by silica gel column chromatography with dichloromethane: n-hexane = 1:10 (volume ratio) as eluent to obtain about 35.6 g of product 8b with a yield of 79%. MS (ASAP) = 342.

[0210] Under anhydrous and anaerobic conditions, the intermediate 8b (35 g, 102 mmol) was added to a 1000 mL three-necked flask, and then 300 mL anhydrous tetrahydrofuran was injected into the flask. The reaction system was stirred at -78°C, and then n-butyllithium-n-hexane solution (40.8 mL, 122.4 mmol) was slowly added dropwise into the reaction system. The reaction system was then continuously stirred at -78°C for 3 hours. Then, the reactant B (13.5 g, 122.4 mmol) was dissolved in 150 mL anhydrous tetrahydrofuran and injected into the reaction system. The reaction system was stirred at -78°C for 2 hours, and then gradually warmed to room temperature and continuously stirred for 12 hours. Finally, deionized water was added to quench the reaction, and the solvent was removed. The resulting product was dissolved in a mixture of concentrated hydrochloric acid / glacial acetic acid (75 mL / 300 mL) under a nitrogen atmosphere, and refluxed at 110°C for 8 hours. After the reaction was completed, the reaction solution was separated and dried. The crude product was purified by column chromatography with ethyl acetate: petroleum ether = 1:10 (volume ratio) as eluent to obtain about 30.1 g of crude product 8c with a yield of about 83%. MS (ASAP) = 356.1.

[0211] Under nitrogen atmosphere, intermediate 8c (30 g, 84.2 mmol), bis(pinacolato)diboron (32.1 g, 126.3 mmol), [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride (3.1 g, 4.2 mmol) and potassium acetate (12.4 g, 126.3 mmol) were added into a 500 mL three-neck flask in turn, then 300 mL 1,4-dioxane was injected into the flask. The reaction mixture was stirred at room temperature, then the solvent was refluxed by heating, and the reflux reaction was kept for 10 hours. After the reaction was completed, the reaction system was cooled to room temperature, and the solvent was removed by rotary evaporation. The obtained crude product was purified by column chromatography using dichloromethane: petroleum ether = 1:2 (volume ratio) as the eluent to obtain product 8d about 32.6 g with a yield of 91%. MS (ASAP) = 434.2.

[0212] Under nitrogen atmosphere, intermediate 8d (32 g, 73.7 mmol), reactant U (21.1 g, 61.4 mmol), potassium carbonate (12.7 g, 92.1 mmol), tetrakis(triphenylphosphine)palladium (4.3 g, 3.7 mmol) and 2-dicyclohexylphosphino-2,4,6-triisopropylbiphenyl (3.5 g, 7.4 mmol) were added into a 1000 mL three-neck flask in turn, then 600 mL 1,4-dioxane and 150 mL deionized water were injected into the flask. The reaction mixture was stirred at room temperature, then the solvent was refluxed by heating, and the reflux reaction was kept for 12 hours. After the reaction was completed, the reaction system was cooled to room temperature, extracted with ethyl acetate, and the organic phase was combined, dried, filtered and concentrated. The product (8) was obtained by silica gel column chromatography using dichloromethane: n-hexane = 1:3 (volume ratio) as the eluent, about 32.9 g with a yield of 71%. MS (ASAP) = 629.3.

[0213] 2. Preparation and characterization of OLED device

[0214] The preparation process of the OLED device is described in detail below by specific examples:

[0215]

[0216] a. Cleaning of ITO (indium tin oxide) conductive glass substrate: cleaned with various solvents (e.g. one or more of chloroform, acetone or isopropanol), and then subjected to ultraviolet ozone treatment.

[0217] b. Evaporation: the ITO substrate was moved into a vacuum vapor deposition device, and the substrate was evaporated under high vacuum (1 x 10 -6The HI layer with a thickness of 30 nm was formed by using an electric resistance heating evaporation source at 10-4 Pa, and then the HT-1 layer with a thickness of 50 nm was formed by heating sequentially, and then the HT-2 layer with a thickness of 10 nm was formed by evaporating Compound 1 on the HT-1 layer. Subsequently, the two evaporation sources were used, and the materials were vaporized at different rates, and the weight ratio of BH:BD was 100:3, and the light-emitting layer with a thickness of 25 nm was formed. Then the first electron transport layer was evaporated, and then the ET and LiQ were placed in different evaporation units, and they were co-deposited at a proportion of 50% by weight respectively to obtain the second electron transport layer, and then 1 nm of LiQ was deposited as an electron injection layer, and finally the Al cathode with a thickness of 100 nm was deposited on the electron injection layer.

[0218] c. Packaging: The device was packaged with an ultraviolet hardening resin in a nitrogen glove box.

[0219] The device structure was HI (10) / HT-1 (50) / HT-2 (10) / BH:BD = 100:3 (25) / first ET transport layer (5) / second ET transport layer ET:LiQ = 50:50 (25) / LiQ (1) / Al (100)

[0220] HI (10) / HT-1 (50) / HT-2 (10) / BH:BD = 100:3 (25) / first ET transport layer (0) / second ET transport layer ET:LiQ = 50:50 (30) / LiQ (1) / Al (100)

[0221] The device performance of the above examples and comparative examples was tested, and the details were shown in Table 1; wherein the driving voltage and the current efficiency were tested at 10 mA / cm 2 current density; the device lifetime of T95 was the time when the luminance decayed to 95% at a constant current density of 20 mA / cm 2 .

[0222] Table 1

[0223]

[0224] Compared with the comparative examples, the current efficiency and the lifetime of the device examples 1-8 were obviously improved, which indicated that the organic compound of the present application applied to the electron transport material in the OLED device could improve the current efficiency and the lifetime of the device, and also could reduce the driving voltage of the device.

[0225] The above described embodiments only express several implementation manners of the present application, the description is more specific and detailed, but it cannot be understood as the limitation of the patent scope of the present application. It should be pointed out that for ordinary skilled in the art, without departing from the concept of the present application, several modifications and improvements can be made, which all belong to the protection scope of the present application. Therefore, the protection scope of the patent of the present application should be subject to the appended claims.

Claims

1. An organic compound, characterized by, having the structure of formula (I) wherein X is independently selected from N or CR7, and at least one X is N; R1-R7are independently at each occurrence selected from the group consisting of hydrogen, D, or a straight-chain alkyl group having 1 to 20 C atoms, Cl, Br, F, or an unsubstituted aromatic group having 5 to 60 ring atoms, or an unsubstituted heteroaromatic group having 5 to 60 ring atoms; L is selected from a single bond or the following groups: wherein R 15 -R 42 are each independently selected from the group consisting of hydrogen, D, or a straight-chain alkyl group having 1 to 20 C atoms, Cl, Br, F; m and n are 1; o is selected from any integer between 0 and 4, and p is selected from any integer between 0 and 3.

2. The organic compound according to claim 1, characterized by selected from the group consisting of: one of the following:

3. The organic compound according to claim 2, characterized by selected from the group consisting of: 、 、 、 、 , one of the above.

4. A mixture characterized in that, An organic electronic device comprising at least one organic compound according to any one of claims 1 to 3 or the mixture according to claim 4, and at least one further organic functional material selected from the group consisting of a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, an emitting material, a host material, an organic dye.

5. A composition characterized in that, An organic electronic device comprising at least one organic compound according to any one of claims 1 to 3 or the mixture according to claim 4, and at least one organic solvent.

6. An organic electronic device comprising a functional layer, characterized in that The functional layer comprises at least one organic compound according to any one of claims 1 to 3 or the mixture according to claim 4.

7. Organic electronic device according to claim 6, characterized in that The organic electronic device is selected from the group consisting of an organic light emitting diode, an organic photovoltaic cell, an organic light emitting cell, an organic light emitting field effect transistor, an organic laser, an organic spintronics device, a photodiode, an organic sensor, and an organic plasmonic emitting diode.

8. Organic electronic device according to claim 7, characterized in that The organic electronic device is an organic electroluminescent device and comprises at least one organic compound according to any one of claims 1 to 3 or the mixture according to claim 4.

9. Organic electronic device according to claim 8, characterized in that The functional layer is an electron transport layer.

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