Anthracene compounds, mixtures, compositions and organic electronic devices

Abstract

The present invention provides an anthracene compound, a mixture, a composition and an organic electronic device. The structure of the anthracene compound is shown in the general formula (1), and the anthracene compound can be used as a blue light host material in the functional layer of an electronic device to improve the stability, efficiency and life of the device.

Description

Technical Field

[0001] The invention relates to the field of organic electroluminescence, and in particular to an anthracene compound, a mixture, a composition and an organic electronic device. Background Art

[0002] Organic semiconductor materials have diversity in synthesis, relatively low manufacturing costs and excellent optical and electrical properties. Organic light-emitting diodes (OLEDs) have broad development potential in optoelectronic devices (such as flat-panel displays and lighting) due to their wide viewing angle, fast response time, low operating voltage and thin panel thickness.

[0003] Organic electroluminescence refers to the phenomenon of converting electrical energy into light energy using organic substances. Organic electroluminescent elements that use organic electroluminescence usually have a structure with a positive electrode and a negative electrode and an organic layer between them. In order to improve the efficiency and life of the organic electroluminescent element, the organic layer has a multilayer structure, and each layer contains different organic substances. 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 this organic electroluminescent element, when a voltage is applied between the two electrodes, holes are injected into the organic layer from the positive electrode, and electrons are injected into the organic layer from the negative electrode. When the injected holes meet the electrons, excitons are formed, and light is emitted when the excitons transition back to the ground state. This organic electroluminescent element has the characteristics of self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high responsiveness.

[0004] In order to improve the luminous efficiency of organic light-emitting diodes, various fluorescent and phosphorescent luminescent material systems have been developed. Whether it is fluorescent materials or phosphorescent materials, the development of excellent blue light materials is a huge challenge. At present, the emission spectrum of most blue light fluorescent materials is too wide and the color purity is poor, which is not conducive to high-end display. In addition, the synthesis of such fluorescent materials is also complex, which is not conducive to large-scale mass production. At the same time, the OLED stability of such blue fluorescent materials needs to be further improved.

[0005] The light-emitting layer of the conventional blue light organic electroluminescent element adopts a host-guest doping structure, and the light-emitting material (guest) can be used together with the matrix material (host) as a light-emitting material to improve color purity, luminous efficiency and stability. Since the host material has a great influence on the efficiency and characteristics of the electroluminescent device when the host material / guest system is used as the light-emitting layer of the light-emitting device, the selection of the host material is very important. The conventional blue light host material has poor stability, resulting in a short life of the device. At the same time, these compounds are difficult to achieve deep blue light emission, which has problems in realizing full-color displays. Summary of the invention

[0006] Based on this, the present invention provides an anthracene compound, which can be used as a blue light host material in the functional layer of an electronic device to improve the stability, efficiency and life of the device.

[0007] The present invention is achieved through the following technical solutions:

[0008] An anthracene compound, the structure of which is shown in the general formula (1):

[0009]

[0010] in:

[0011] Ar 1 is selected from substituted or unsubstituted aromatic groups having 6 to 60 ring atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 60 ring atoms, or a combination of these groups;

[0012] L 1 With L 2 are independently selected from a single bond, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms;

[0013] R 1 , R 2 With R 3 is a substituent, each occurrence being independently selected from: -D, a linear alkyl group having 1 to 20 C atoms, a linear alkoxy group having 1 to 20 C atoms, a linear thioalkoxy group having 1 to 20 C atoms, a branched alkyl group having 3 to 20 C atoms, a branched alkoxy group having 3 to 20 C atoms, a branched thioalkoxy group having 3 to 20 C atoms, a cyclic alkyl group having 3 to 20 C atoms, a cyclic alkoxy group having 3 to 20 C atoms, a cyclic thioalkoxy group having 3 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amino group, -CF 3 , -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups;

[0014] m1 is 0, 1, 2, 3, 4, 5, 6, 7 or 8;

[0015] m2 is 0, 1, 2, 3 or 4;

[0016] m3 is 0, 1, 2, 3 or 4.

[0017] The present invention also provides a mixture, which comprises the anthracene compound as described above and at least one organic functional material, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent bodies or host materials.

[0018] The present invention also provides a composition, which comprises the anthracene compound as described above or the mixture as described above, and at least one organic solvent.

[0019] The present invention also provides an organic electronic device, which comprises the anthracene compound as described above, the mixture as described above, or is prepared from the composition as described above.

[0020] Compared with the prior art, the anthracene compounds of the present invention have the following beneficial effects:

[0021] The organic compound described in the present invention comprises the structure of anthracene ring, five-membered heterocyclic ring and seven-membered heterocyclic ring, and introduces a hole transport group, so that the molecule has good stability and high color purity. When used as a blue light main material in an organic electronic device, the device can achieve an ideal electrical balance state, thereby improving the stability, efficiency and life of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0022] Figure 1 A schematic diagram of an OLED device provided in one embodiment of the present invention; in the figure, 101 is a substrate, 102 is an anode, 103 is a hole injection layer, 104 is a hole transport layer, 105 is a light-emitting layer, 106 is an electron transport layer, and 107 is a cathode. DETAILED DESCRIPTION

[0023] For ease of understanding of the present invention, the present invention will be described more fully below with reference to relevant embodiments. Preferred embodiments of the present invention are provided in the embodiments. However, the present invention can be implemented in many different forms and is not limited to the embodiments described herein. On the contrary, the purpose of providing these embodiments is to make the understanding of the disclosure of the present invention more thorough and comprehensive.

[0024] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as those commonly understood by those skilled in the art of the present invention. The terms used herein in the specification of the present invention are only for the purpose of describing specific embodiments and are not intended to limit the present invention. The term "and / or" used herein includes any and all combinations of one or more related listed items.

[0025] In the present invention, composition and printing ink, or ink have the same meaning and can be interchanged.

[0026] In the present invention, aromatic group, aromatic series and aromatic ring system have the same meaning and can be interchanged.

[0027] In the present invention, heteroaromatic group, heteroaromatic series and heteroaromatic ring system have the same meaning and can be interchanged.

[0028] In the present invention, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0029] In the present invention, when the same substituent appears multiple times, it can be independently selected from different groups. 1 , then R 1 Can be independently selected from different groups.

[0030] In the present invention, "substituted or unsubstituted" means that the defined group may be substituted or unsubstituted. When the defined group is substituted, it should be understood that the defined group may be substituted by one or more substituents R, wherein R is selected from but not limited to: deuterium atom (D), cyano, isocyano, nitro or halogen, alkyl containing 1-20 C atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, -NR'R", silane, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, haloformyl, formyl, isocyanate, thiocyanate, isothiocyanate, hydroxyl, trifluoromethyl, and the above groups may be further substituted by substituents acceptable in the art; it is understandable that R' and R" in -NR'R" are independently selected from but not limited to: H, deuterium, thiocyanate, isothiocyanate, hydroxyl, trifluoromethyl. Atom, cyano group, isocyano group, nitro group or halogen group, alkyl group containing 1-10 C atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms. Preferably, R is selected from but not limited to: deuterium atom, cyano group, isocyano group, nitro group or halogen group, alkyl group containing 1-10 C atoms, heterocyclic group containing 3-10 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, silane group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, haloformyl group, formyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, and the above groups can also be further substituted by substituents acceptable in the art.

[0031] In the present invention, the "number of ring atoms" refers to the number of atoms in the atoms constituting the ring itself of a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) in which atoms are bonded to form a ring. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring atoms. The same is true for the "number of ring atoms" described below unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

[0032] "Aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom, which can be a monocyclic aromatic group, a condensed aromatic group, or a polycyclic aromatic group. For polycyclic rings, at least one is an aromatic ring system. For example, "substituted or unsubstituted aromatic group having 6 to 40 ring atoms" refers to an aromatic group containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aromatic group having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted aromatic group having 6 to 14 ring atoms, and the aromatic group is optionally further substituted; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, perylene, naphthyl, fluorenyl, dinaphthylenyl, acenaphthene and derivatives thereof. It is understandable that multiple aromatic groups may also be interrupted by short non-aromatic units (e.g. <10% non-H atoms, such as C, N or O atoms), specifically acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aromatic groups.

[0033] "Heteroaryl or heteroaromatic group" means that at least one carbon atom is replaced by a non-carbon atom on the basis of an aryl group, and the non-carbon atom can be an N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" means a heteroaryl having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl having 6 to 14 ring atoms, and the heteroaryl group is optionally further substituted, and suitable examples include but are not limited to: thienyl, furanyl, pyrrolyl, imidazolyl, triazolyl, imidazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyridinyl, oxazine, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzothiophenyl, benzofuranyl, indolyl, carbazolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothiphenyl, furopyrrolyl, furofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, quinolyl, isoquinolyl, o-naphthyl, quinoxalinyl, phenanthridinyl, primary pyridyl, quinazolinyl, quinazolinone, dibenzothiophenyl, dibenzofuranyl, carbazolyl and derivatives thereof.

[0034] In the present invention, "alkyl" may refer to a linear, branched and / or cyclic alkyl group. The carbon number of the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6. Phrases containing this term, such as "C 1-9 "Alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, each occurrence of which can be independently C 1 Alkyl, C 2 Alkyl, C 3 Alkyl, C 4 Alkyl, C 5 Alkyl, C 6 Alkyl, C 7 Alkyl, C 8 Alkyl or C 9Alkyl. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl decyl, 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-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, adamantane, and the like.

[0035] In the present invention, the substituent abbreviations correspond to: n-normal, sec-secondary, i-iso, t-tertiary, o-ortho, m-meta, p-para, Me methyl, Et ethyl, Pr propyl, Bu butyl, Am n-pentyl, Hx hexyl, Cy cyclohexyl.

[0036] "Amine" refers to an amine derivative having the formula -N(X) 2 The structural features of wherein each "X" is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, etc. Non-limiting types of amine groups include -NH 2 、-N(alkyl) 2 、-NH(alkyl), -N(cycloalkyl) 2 、-NH(cycloalkyl), -N(heterocyclic) 2 、-NH(heterocyclic group), -N(aryl group) 2 , -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclyl), -N(cycloalkyl)(heterocyclyl), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), and the like.

[0037] In the present invention, unless otherwise defined, a hydroxyl group refers to -OH, a carboxyl group refers to -COOH, a carbonyl group refers to -C(=O)-, an amino group refers to -NH2, a formyl group refers to -C(=O)H, a haloformyl group refers to -C(=O)Z (wherein Z represents a halogen), a carbamoyl group refers to -C(=O)NH2, an isocyanate group refers to -NCO, and an isothiocyanate group refers to -NCS.

[0038] The term "alkoxy" refers to a group of the structure "-O-alkyl", i.e., an alkyl group as defined above attached to another group via an oxygen atom. Phrases containing this term, suitable examples include, but are not limited to, methoxy (-O-CH 3 or -OMe), ethoxy (-O-CH 2 CH 3 or -OEt) and tert-butyloxy (-OC(CH 3 ) 3 or -OtBu).

[0039] In the present invention, "*" connected to a single bond indicates a connection or fusion site;

[0040] In the present invention, when a linking site is not specified in a group, it means that any linking site in the group can be used as a linking site;

[0041] In the present invention, when the fusion site is not specified in the group, it means that any fusion site in the group can be used as the fusion site, and preferably two or more sites in the ortho position in the group are fusion sites;

[0042] In the present invention, when a group contains multiple substituents with the same symbol, the substituents may be the same or different from each other. 6 R on the benzene ring 1 May be the same as or different from each other.

[0043] In the present invention, the single bond to which the substituent is connected runs through the corresponding ring, indicating that the substituent can be connected to any position of the ring, for example In which R is connected to any substitutable position of the benzene ring; express Can be used with The benzene ring can be fused at any position.

[0044] In the embodiment of the present invention, the energy level structure of the organic material, the triplet energy levels ET, HOMO, and LUMO play a key role. The determination of these energy levels is introduced below.

[0045] HOMO and LUMO energy levels can be measured by photoelectric effects, such as XPS (X-ray photoelectron spectroscopy) and UPS (ultraviolet photoelectron spectroscopy) or by cyclic voltammetry (hereafter referred to as CV). Recently, quantum chemical methods, such as density functional theory (hereafter referred to as DFT), have also become effective methods for calculating molecular orbital energy levels.

[0046] The triplet energy level ET1 of the organic material can be measured by low-temperature time-resolved luminescence spectroscopy, or obtained by quantum simulation calculation (such as by Time-dependent DFT), such as by the commercial software Gaussian 09W (Gaussian Inc.). The specific simulation method can be found in WO2011141110 or as described below in the embodiments.

[0047] It should be noted that the absolute values ​​of HOMO, LUMO, and ET1 depend on the measurement method or calculation method used, and even for the same method, different evaluation methods, such as the starting point and the peak point on the CV curve, may give different HOMO / LUMO values. Therefore, a reasonable and meaningful comparison should be made using the same measurement method and the same evaluation method. In the description of the embodiments of the present invention, the values ​​of HOMO, LUMO, and ET1 are based on the simulation of Time-dependent DFT, but do not affect the application of other measurement or calculation methods.

[0048] In the present invention, (HOMO-1) is defined as the second highest occupied orbital energy level, (HOMO-2) is the third highest occupied orbital energy level, and so on. (LUMO+1) is defined as the second lowest unoccupied orbital energy level, (LUMO+2) is the third lowest occupied orbital energy level, and so on.

[0049] According to the present invention, the cyclic alkyl or cycloalkyl group has the same meaning and can be interchanged.

[0050] The present invention provides an anthracene compound, the structure of which is shown in the general formula (1):

[0051]

[0052] in:

[0053] Ar 1 is selected from substituted or unsubstituted aromatic groups having 6 to 60 ring atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 60 ring atoms, or a combination of these groups;

[0054] L 1 With L 2are independently selected from a single bond, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms;

[0055] R 1 , R 2 With R 3 is a substituent, each occurrence being independently selected from: -D, a linear alkyl group having 1 to 20 C atoms, a linear alkoxy group having 1 to 20 C atoms, a linear thioalkoxy group having 1 to 20 C atoms, a branched alkyl group having 3 to 20 C atoms, a branched alkoxy group having 3 to 20 C atoms, a branched thioalkoxy group having 3 to 20 C atoms, a cyclic alkyl group having 3 to 20 C atoms, a cyclic alkoxy group having 3 to 20 C atoms, a cyclic thioalkoxy group having 3 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amino group, -CF 3 , -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups;

[0056] m1 is 0, 1, 2, 3, 4, 5, 6, 7 or 8;

[0057] m2 is 0, 1, 2, 3 or 4;

[0058] m3 is 0, 1, 2, 3 or 4.

[0059] In a specific example, Ar 1 is selected from substituted or unsubstituted aromatic groups containing 6 to 30 ring atoms, substituted or unsubstituted heteroaromatic groups containing 6 to 30 ring atoms. 1 It is selected from a substituted or unsubstituted aromatic group containing 6 to 16 ring atoms and a substituted or unsubstituted heteroaromatic group containing 6 to 16 ring atoms.

[0060] In a specific example, Ar 1 Select from any of the following groups:

[0061]

[0062] in:

[0063] Each occurrence of X is independently selected from CR 4 or N; preferably, each occurrence of X is independently selected from CR 4 ;

[0064] Y is selected from NR 5 , CR 6 R 7 、SiR 6 R 7 ,O,S,S=O or SO 2 ;

[0065] R 4 , R 5 , R 6 , R 7 Each occurrence is independently selected from: -H, -D, straight-chain alkyl with 1 to 20 C atoms, straight-chain alkoxy with 1 to 20 C atoms, straight-chain thioalkoxy with 1 to 20 C atoms, branched-chain alkyl with 3 to 20 C atoms, branched-chain alkoxy with 3 to 20 C atoms, branched-chain thioalkoxy with 3 to 20 C atoms, cyclic alkyl with 3 to 20 C atoms, cyclic alkoxy with 3 to 20 C atoms, cyclic thioalkoxy with 3 to 20 C atoms, silyl, keto with 1 to 20 C atoms, alkoxycarbonyl with 2 to 20 C atoms, aryloxycarbonyl with 7 to 20 C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, amine, -CF 3 , -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group having 6 to 50 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 50 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 50 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 50 ring atoms, or a combination of these groups;

[0066] R 6 and R 7 They may or may not form a ring with each other.

[0067] It can be understood that in the present invention, when X is a linking site, X is C; when Y is a linking site, Y is selected from N.

[0068] In a specific example, the structure of the anthracene compound is selected from any one of the structures shown in general formulas (2-1) to (2-4):

[0069]

[0070] In a specific example, R 4Each occurrence is independently selected from: -H, -D, straight-chain alkyl having 1 to 10 C atoms, branched-chain alkyl having 3 to 10 C atoms, cyclic alkyl having 3 to 10 C atoms, silyl, isocyano, nitro, amine, -CF 3 , -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms, or a combination of these groups; further, R 4 Each occurrence is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 8 C atoms, a branched-chain alkyl group having 3 to 8 C atoms, a cyclic alkyl group having 3 to 8 C atoms, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms, or a combination of these groups.

[0071] Preferably, the substituent R is selected from -D, a linear alkyl group having 1 to 4 C atoms, a branched alkyl group having 3 to 4 C atoms, or a phenyl group, or a pyridyl group.

[0072] Furthermore, R 4 Each occurrence is independently selected from: -H or -D.

[0073] In a specific example, R 5 Each occurrence is independently selected from: a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms, a cyclic alkyl group having 3 to 10 C atoms, a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms, or a combination of these groups; further, R 5 Each occurrence is independently selected from: a substituted or unsubstituted aromatic group having 6 to 13 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 13 ring atoms, or a combination of these groups; further, R 4 Each occurrence is independently selected from: methyl, ethyl, isopropyl, tert-butyl, phenyl, pyridyl, pyrimidinyl, triazinyl, biphenyl, terphenyl or naphthyl.

[0074] In a specific example, R 6 , R 7 Each occurrence is independently selected from: -H, -D, a straight chain alkyl group having 1 to 8 C atoms, a branched chain alkyl group having 3 to 8 C atoms, or a cyclic alkyl group having 3 to 8 C atoms, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms, or a combination of these groups; further, R 6 , R 7Each occurrence is independently selected from: -H, -D, methyl, ethyl, isopropyl, phenyl, pyridyl, pyrimidyl, triazinyl, biphenyl, terphenyl, or naphthyl.

[0075] In one embodiment, Ar 1 Select from any of the following groups:

[0076]

[0077] Wherein: * indicates the connection site.

[0078] In a specific example, R 1 , R 2 and R 3 Each occurrence is independently selected from: -D, straight-chain alkyl having 1 to 10 C atoms, straight-chain alkoxy having 1 to 10 C atoms, straight-chain thioalkoxy having 1 to 10 C atoms, branched-chain alkyl having 3 to 10 C atoms, branched-chain alkoxy having 3 to 10 C atoms, branched-chain thioalkoxy having 3 to 10 C atoms, cyclic alkyl having 3 to 20 C atoms, cyclic alkoxy having 3 to 10 C atoms, cyclic thioalkoxy having 3 to 10 C atoms, silyl, keto having 1 to 10 C atoms, alkoxycarbonyl having 2 to 10 C atoms, aryloxycarbonyl having 7 to 10 C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, amine, -CF 3 , -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaryloxy group having 6 to 30 ring atoms, or a combination of these groups.

[0079] Preferably, R 1 , R 2 With R 3 Each occurrence is independently selected from: -D, linear alkyl with 1 to 8 C atoms, branched alkyl with 3 to 8 C atoms, cyclic alkyl with 3 to 8 C atoms, silyl, -CN, isocyano, hydroxy, nitro, -CF 3 , -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms, or a combination of these groups.

[0080] More specifically, R 1 , R 2 and R 3Each occurrence is independently selected from: -D, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, adamantyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triazine, pyridyl, pyrimidinyl, imidazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, dibenzothienyl, dibenzofuranyl, phenyl-substituted carbazolyl, fluorenyl, alkyl-substituted fluorenyl with 1 to 10 C atoms.

[0081] In one embodiment, L 1 With L 2 are independently selected from a single bond, a substituted or unsubstituted aromatic group having 6 to 14 ring atoms, and a substituted or unsubstituted heteroaromatic group having 6 to 14 ring atoms.

[0082] In a specific example, L 1 With L 2 are independently selected from a single bond or any of the following groups:

[0083]

[0084] in:

[0085] X 1 Each occurrence is independently selected from CR 8 or N;

[0086] Y 1 Selected from NR 9 , CR 10 R 11 、SiR 10 R 11 ,O,S,S=O or SO 2 ;

[0087] R 8 , R 9 , R 10 , R 11Each occurrence is independently selected from: -H, -D, straight-chain alkyl with 1 to 20 C atoms, straight-chain alkoxy with 1 to 20 C atoms, straight-chain thioalkoxy with 1 to 20 C atoms, branched-chain alkyl with 3 to 20 C atoms, branched-chain alkoxy with 3 to 20 C atoms, branched-chain thioalkoxy with 3 to 20 C atoms, cyclic alkyl with 3 to 20 C atoms, cyclic alkoxy with 3 to 20 C atoms, cyclic thioalkoxy with 3 to 20 C atoms, silyl, keto with 1 to 20 C atoms, alkoxycarbonyl with 2 to 20 C atoms, aryloxycarbonyl with 7 to 20 C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, -CF 3 , -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group having 6 to 50 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 50 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 50 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 50 ring atoms, or a combination of these groups.

[0088] It can be understood that in the present invention, when X 1 When X is the attachment site, 1 For C.

[0089] In a specific example, R 8 , R 9 , R 10 , R 11 Each occurrence is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms, or a combination of these groups.

[0090] The substituents are as defined above.

[0091] In one embodiment, L 1 With L 2 are independently selected from a single bond or any of the following groups:

[0092]

[0093] In one embodiment, the structure of the anthracene compound is selected from the general formula (3-1) or (3-2):

[0094]

[0095] In one embodiment, L in the general formula (3-1) or (3-2) 1 , L 2 is selected from a single bond or a phenyl group or a phenyl group substituted with a methyl group. In one embodiment, L in the general formula (3-1) or (3-2) 1 is selected from single bonds;

[0096] In one embodiment, L in the general formula (3-1) or (3-2) 2 Selected from a single bond or phenyl or phenyl substituted by methyl.

[0097] Specifically, the anthracycline compound according to the present invention is selected from the following structures but is not limited thereto:

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104] The anthracene organic compound of the present invention can be used as a functional material in the functional layer of an electronic device. The organic functional layer includes, but is not limited to, a hole injection layer (HIL), a hole transport layer (HTL), an electron transport layer (ETL), an electron injection layer (EIL), an electron blocking layer (EBL), a hole blocking layer (HBL), and an emitting layer (EML).

[0105] In one embodiment, the anthracene organic compound according to the present invention can be used as a light-emitting material in a light-emitting layer, preferably, can be used as a main material of the light-emitting layer in the light-emitting layer.

[0106] The present invention further relates to a mixture comprising at least one anthracene organic compound as described above, and at least another organic functional material, wherein the another organic functional material can be selected from a hole injection material (HIM), a hole transport material (HTM), an electron transport material (ETM), an electron injection material (EIM), an electron blocking material (EBM), a hole blocking material (HBM), a light-emitting material (Emitter), a host material (Host) and an organic dye.

[0107] In one embodiment, the another organic functional material is selected from a guest material; further, the another organic functional material is selected from a blue light guest material; preferably, the blue light guest material is selected from a compound as described in formula (4) below.

[0108] The present invention also relates to a composition comprising at least one anthracene organic compound or mixture as described above, and at least one organic solvent; the at least one organic solvent is selected from aromatic or heteroaromatic, ester, aromatic ketone or aromatic ether, aliphatic ketone or aliphatic ether, alicyclic or olefin compounds, or borate or phosphate compounds, or a mixture of two or more solvents.

[0109] Examples of aromatic or heteroaromatic solvents suitable for the present invention include, but are not limited to: p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, 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-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α, α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoate, ethyl 2-furoate, etc.;

[0110] Examples of aromatic ketone-based solvents suitable for the present invention include, but are not limited to: 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, etc.;

[0111] Examples of aromatic ether-based solvents suitable for the present invention 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-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether;

[0112] Examples of aliphatic ketone-based solvents suitable for the present invention include, but are not limited to: 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, phorone, isophorone, di-n-amyl ketone, etc.; or aliphatic ethers, for example, amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, etc.

[0113] Examples of ester-based solvents suitable for the present invention include, but are not limited to, alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. Octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate are particularly preferred.

[0114] The solvent may be used alone or as a mixture of two or more organic solvents.

[0115] In certain preferred embodiments, a composition according to the present invention comprises at least one anthracycline organic compound or mixture as described above and at least one organic solvent, and may further comprise another organic solvent. Examples of another organic solvent include (but are not limited to): methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, indene and / or mixtures thereof.

[0116] In some preferred embodiments, solvents particularly suitable for the present invention are solvents having a Hansen solubility parameter in the following ranges:

[0117] δd (dispersion force) is in the range of 17.0 to 23.2 MPa1 / 2, especially in the range of 18.5 to 21.0 MPa1 / 2;

[0118] δp (polar force) is in the range of 0.2 to 12.5 MPa1 / 2, especially in the range of 2.0 to 6.0 MPa1 / 2;

[0119] δh (hydrogen bonding force) is in the range of 0.9 to 14.2 MPa1 / 2, and particularly in the range of 2.0 to 6.0 MPa1 / 2.

[0120] According to the composition of the present invention, the organic solvent should be selected considering its boiling point parameter. In the present invention, the boiling point of the organic solvent is ≥150°C; preferably ≥180°C; more preferably ≥200°C; more preferably ≥250°C; and most preferably ≥300°C. Boiling points within these ranges are beneficial for preventing nozzle clogging of the inkjet print head. The organic solvent can be evaporated from the solvent system to form a film containing a functional material.

[0121] In a preferred embodiment, the composition according to the invention is a solution.

[0122] In another preferred embodiment, the composition according to the invention is a suspension.

[0123] The composition in the embodiment of the present invention may include 0.01wt% to 10wt% of the anthracene organic compound or mixture according to the present invention, preferably 0.1wt% to 8wt%, more preferably 0.2 to 5wt%, and most preferably 0.25wt% to 3wt%.

[0124] The present invention also relates to the use of the composition as a coating or printing ink in the preparation of organic electronic devices, and particularly preferably a preparation method by printing or coating.

[0125] Among them, suitable printing or coating techniques include (but are not limited to) inkjet printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, twist roller printing, lithography, flexographic printing, rotary printing, spraying, brushing or pad printing, slot extrusion coating, etc. The preferred ones are gravure printing, spray printing and inkjet printing. The solution or suspension may further include one or more components such as surfactant compounds, lubricants, wetting agents, dispersants, hydrophobic agents, adhesives, etc., for adjusting viscosity, film-forming properties, improving adhesion, etc. Relevant printing technology and its related requirements for relevant solutions, such as solvents and concentrations, viscosity, etc.

[0126] The present invention also provides an application of the anthracene organic compound, mixture or composition described above in an organic electronic device. The technical solution is as follows:

[0127] An organic electronic device comprises the anthracene organic compound, a mixture or a combination thereof as described above.

[0128] Further, an organic electronic device comprises a first electrode, a second electrode, and one or more organic functional layers located between the first electrode and the second electrode, wherein the organic functional layer comprises the anthracene organic compound, a mixture or is prepared from the above-mentioned composition. The functional layer is selected from a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron blocking layer (EBL), an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0129] In the present invention, the organic electronic device may be selected from, but not limited to, organic light emitting diodes (OLEDs), organic photovoltaic cells, organic light emitting cells, organic field effect transistors, organic light emitting field effect transistors, organic lasers, organic spintronic devices, organic sensors and organic plasmon emitting diodes, etc., and OLEDs are particularly preferred.

[0130] The present invention further relates to an organic electronic device, comprising: a cathode, an anode, and one or more organic functional layers located between the cathode and the anode, wherein the organic functional layer comprises at least one light-emitting layer, wherein the light-emitting layer material comprises a host material and a guest material, wherein the host material comprises the anthracene organic compound of formula (1), and the guest material comprises the compound of formula (4):

[0131]

[0132] in:

[0133] Ar 4 -Ar 7 independently selected from substituted or unsubstituted aromatic groups containing 6 to 60 ring atoms, or substituted or unsubstituted heteroaromatic groups containing 6 to 60 ring atoms, or combinations of these groups;

[0134] R 12each occurrence is independently selected from -H, -D, or a straight-chain alkyl group having 1 to 20 C atoms, 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-chain alkyl group having 3 to 20 C atoms, or a branched-chain alkoxy group having 3 to 20 C atoms, or a branched-chain thioalkoxy group having 3 to 20 C atoms, or a cyclic alkyl group having 3 to 20 C atoms, or a cyclic alkoxy group having 3 to 20 C atoms, or a cyclic thioalkoxy group having 3 to 20 C atoms, or 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 haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, or an isothiocyanate group, a hydroxyl group, a nitro group, an amino group, a CF 3 , Cl, Br, F, I, or a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups;

[0135] s is any integer selected from 0-8.

[0136] The further description of the anthracene organic compound represented by formula (1) is as described above.

[0137] In one embodiment, Ar 4 -Ar 7 Independently selected from substituted or unsubstituted aromatic groups containing 6 to 14 ring atoms, or substituted or unsubstituted heteroaromatic groups containing 6 to 14 ring atoms, or combinations of these groups.

[0138] In one embodiment, the Ar 4 -Ar 7 Contains any of the following structures:

[0139]

[0140] in:

[0141] Each occurrence of V is independently selected from CR 13 or N;

[0142] W is selected from NR 14 , CR 14 R 15 、SiR 14 R 15 ,O,S,S=O or SO 2 ;

[0143] R13 -R 15 each occurrence is independently selected from -H, -D, or a straight-chain alkyl group having 1 to 20 C atoms, 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-chain alkyl group having 3 to 20 C atoms, or a branched-chain alkoxy group having 3 to 20 C atoms, or a branched-chain thioalkoxy group having 3 to 20 C atoms, or a cyclic alkyl group having 3 to 20 C atoms, or a cyclic alkoxy group having 3 to 20 C atoms, or a cyclic thioalkoxy group having 3 to 20 C atoms, or 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 haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, or an isothiocyanate group, a hydroxyl group, a nitro group, an amino group, a CF 3 , Cl, Br, F, I, or a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.

[0144] Furthermore, R 13 -R 15 Each occurrence is independently selected from -H, -D, or a straight-chain alkyl group having 1 to 10 C atoms, or a branched-chain alkyl group having 3 to 10 C atoms, or a cyclic alkyl group having 3 to 10 C atoms, or a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, or a combination of these groups.

[0145] Furthermore, R 13 -R 15 Each occurrence is independently selected from -H, -D, straight chain alkyl having 1 to 10 C atoms, or branched or cyclic alkyl having 3 to 10 C atoms, or phenyl.

[0146] In one embodiment, formula (2) is selected from the following general formula:

[0147]

[0148] Preferably, R 13 Each occurrence is independently selected from -H, -D, straight chain alkyl having 1 to 10 C atoms, or branched or cyclic alkyl having 3 to 10 C atoms, or phenyl.

[0149] Further, formula (2) is selected from the following general formula:

[0150]

[0151] Wherein: W has the same meaning as above.

[0152] The structures of the organic compounds described in formula (2) of the present invention are listed below, but are not limited thereto:

[0153]

[0154] In one embodiment, the organic electronic device comprises a cathode, an anode, a hole transport layer, a light emitting layer, and an electron transport layer.

[0155] In one embodiment, the organic electronic device comprises a cathode, an anode, a hole transport layer, a hole injection layer, a light emitting layer, and an electron transport layer.

[0156] In one embodiment, the organic electronic device comprises a cathode, an anode, a hole transport layer, a hole injection layer, a light emitting layer, an electron blocking layer, and an electron transport layer.

[0157] Materials suitable for use in these functional layers are described in detail above and in WO2010135519A1, US20090134784A1 and WO2011110277A1, the entire contents of these three patent documents are hereby incorporated herein by reference.

[0158] The light emitting device described above, especially OLED, comprises a substrate, an anode, at least one light emitting layer, and a cathode.

[0159] The substrate can be opaque or transparent. A transparent substrate can be used to make a transparent light-emitting device. For example, see Bulovic et al. Nature 1996, 380, p29, and Gu et al., Appl. Phys. Lett. 1996, 68, p2606. The substrate can be rigid or elastic. The substrate can be plastic, metal, semiconductor wafer or glass. It is best that the substrate has a smooth surface. Substrates without surface defects are particularly ideal. In a preferred embodiment, the substrate is flexible and can be selected from polymer films or plastics, and its glass transition temperature Tg is above 150°C, preferably above 200°C, more preferably above 250°C, and preferably above 300°C. Examples of suitable flexible substrates include poly (ethylene terephthalate) (PET) and polyethylene glycol (2,6-naphthalene) (PEN).

[0160] The anode may include a conductive metal or metal oxide, or a conductive polymer. The anode can easily inject holes into the hole injection layer (HIL) or the hole transport layer (HTL) or the light-emitting layer. In one embodiment, the absolute value of the difference between the work function of the anode and the HOMO energy level or valence band energy level of the light-emitting body in the light-emitting layer or the p-type semiconductor material as the HIL or HTL or the electron blocking layer (EBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. Examples of anode materials include, but are not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), etc. Other suitable anode materials are known and can be easily selected for use by a person of ordinary skill in the art. The anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc. In certain embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to prepare devices according to the present invention.

[0161] The cathode may include a conductive metal or metal oxide. The cathode can easily inject electrons into the EIL or ETL or directly into the light-emitting layer. In one embodiment, the absolute value of the difference between the work function of the cathode and the LUMO energy level or conduction band energy level of the luminophore in the light-emitting layer or the n-type semiconductor material as the electron injection layer (EIL) or the electron transport layer (ETL) or the hole blocking layer (HBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials that can be used as cathodes of OLEDs may be used as cathode materials for the device of the present invention. Examples of cathode materials include, but are not limited to, Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The cathode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.

[0162] In a preferred embodiment, the organic electronic device of the present invention is selected from solution-type OLED.

[0163] In a preferred embodiment, in the light-emitting device according to the present invention, the light-emitting layer thereof is prepared by the composition according to the present invention.

[0164] According to the light emitting device of the present invention, the light emission wavelength is between 300 and 1000 nm, preferably between 350 and 900 nm, and more preferably between 400 and 800 nm.

[0165] The present invention also relates to the application of the organic electronic device according to the present invention in various electronic devices, including, but not limited to, display devices, lighting devices, light sources, sensors and the like.

[0166] The present invention also relates to electronic devices comprising the organic electronic device according to the present invention, including, but not limited to, display devices, lighting devices, light sources, sensors and the like.

[0167] The present invention will be described below in conjunction with preferred embodiments, but the present invention is not limited to the following embodiments. It should be understood that the attached claims summarize the scope of the present invention. Under the guidance of the concept of the present invention, those skilled in the art should be aware that certain changes made to the various embodiments of the present invention will be covered by the spirit and scope of the claims of the present invention. Specific embodiments

[0169] The anthracene compounds and the preparation method of the present invention are further described in detail below in conjunction with specific examples. The raw materials used in the following examples are all commercially available products unless otherwise specified.

[0170] Example 1

[0171] This embodiment provides an anthracene compound, and the specific synthesis route is as follows:

[0172]

[0173] Synthesis of intermediate 1-1:

[0174] Benzofuran (8.63 mL, 80.0 mmol) was dissolved in dichloromethane (50 mL) and cooled to -10°C. Bromine (4.83 mL, 88.0 mmol) was dissolved in 15 mL dichloromethane and slowly added to the above solution at -10°C and stirred for 1 hour. 1 M NaOH aqueous solution (4 mL) was added to the reaction mixture. 2 S 2 O 3 The solution was washed and extracted with dichloromethane. The solvent was evaporated and the residue was dissolved in 50 ml of ethanol. Then a saturated KOH ethanol solution (80 ml) was added at 0°C and the mixture was refluxed for 4 hours. After the reaction was completed, the reaction solution was extracted with ethyl acetate (50 ml x 3), washed with saturated brine, and washed with anhydrous Na 2 SO 4 After drying, the mixture was filtered and the solvent was removed by rotary evaporation to obtain intermediate 1-1 as a yellow oil (7.05 g, 45%). MS (ASAP) = 196.0.

[0175] Synthesis of intermediate 1-2:

[0176] Intermediate 1-1 (1.96 g, 10 mmol) and 2-hydroxyphenylboronic acid (1.38 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh 3 ) 4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100 °C for 6 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain intermediate 1-2 by organic phase column chromatography and recrystallization. Yield: 52%. MS (ASAP) = 210.1.

[0177] Synthesis of intermediate 1-3:

[0178] Place intermediate 1-2 (10 g, 47.6 mmol) in a 500 ml two-necked bottle, add 100 ml of DMF until the solid is completely dissolved, weigh NBS (8.5 g, 47.6 mmol) and place it in a constant pressure dropping funnel, dissolve it in 100 ml of DMF, slowly add dropwise, and react at room temperature for 12 hours. Spin dry, wash with water, and column chromatography (eluent: DCM:PE = 1:2 (volume ratio)) to obtain a colorless oil with a yield of 81%. MS (ASAP) = 288.0.

[0179] Synthesis of intermediate 1-4:

[0180] Intermediate 1-3 (5 g, 17 mmol) and 2-fluoro-4-chlorophenylboronic acid pinacol ester (6.7 g, 26 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh 3 ) 4 (1.0 g, 0.87 mmol) and potassium carbonate (7.0 g, 51 mmol). Stir at 100 °C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and perform organic phase column chromatography (eluent: DCM:PE=1:2 (volume ratio)) to obtain a white solid with a yield of 60%. MS (ASAP) = 338.1.

[0181] Synthesis of intermediate 1-5:

[0182] Intermediate 1-4 (5 g, 14.8 mmol) was dissolved in DMF (100 ml) solution, and potassium carbonate (10.2 g, 74 mmol) was added. Stir at 150°C for 12 h under nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then extracted with DCM and washed with water. The organic phase was subjected to column chromatography (eluent: DCM:PE = 1:5 (volume ratio)) to obtain a white solid with a yield of 44%. MS (ASAP) = 318.1.

[0183] Synthesis of intermediate 1-6:

[0184] Weigh 1-5 (5 g, 15.7 mmol), (Bpin) 2 (4.8g,18.8mmol), AcOK(9.8g,100mmol), Pd(dppf)Cl 2 (0.74 g, 1.0 mmol), t-Bu 3 P (0.39 g, 1.94 mmol) was placed in a 250 mL three-necked flask, 100 ml of 1,4-dioxane was added, nitrogen was replaced, and the reaction was carried out at 100°C for 12 h. The mixture was spin-dried, washed with water, and subjected to column chromatography (eluent: PE:DCM = 5:1 (volume ratio)) to obtain a colorless oily substance with a yield of 65%. MS (ASAP) = 410.2.

[0185] Synthesis of compound 1:

[0186] Intermediate 1-6 (4.1 g, 10 mmol) and 9-bromo-10-(1-naphthyl)anthracene (3.1 g, 12 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh 3 ) 4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain compound 1 by organic phase column chromatography and recrystallization. Yield: 58%. MS (ASAP) = 586.2.

[0187] Example 2

[0188] This embodiment provides an anthracene compound, and the specific synthesis route is as follows:

[0189]

[0190] Synthesis of intermediate 2-1:

[0191] The intermediate 9-bromo-10-(1-naphthyl)anthracene (3.8 g, 10 mmol) and 4'-bromo-4-biphenylboronic acid (2.7 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh 3 ) 4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain intermediate 2-1 by organic phase column chromatography and recrystallization. Yield: 88%. MS (ASAP) = 534.1.

[0192] Synthesis of compound 2:

[0193] Intermediate 2-1 (5.3 g, 10 mmol) and 1-6 (4.1 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh 3 ) 4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain compound 2 by organic phase column chromatography and recrystallization. Yield: 73%. MS (ASAP) = 738.3.

[0194] Example 3

[0195] This embodiment provides an anthracene compound, and the specific synthesis route is as follows:

[0196]

[0197] Synthesis of intermediate 3-1:

[0198] The intermediate 9-bromo-10-(1-naphthyl)anthracene (3.8 g, 10 mmol) and 4-bromo-1-naphthylboronic acid (2.5 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh 3 ) 4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain intermediate 3-1 by organic phase column chromatography and recrystallization. Yield: 82%. MS (ASAP) = 508.1.

[0199] Synthesis of compound 3:

[0200] Intermediate 3-1 (5.1 g, 10 mmol) and 1-6 (4.1 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh 3 ) 4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain compound 3 by organic phase column chromatography and recrystallization. Yield: 79%. MS (ASAP) = 712.2.

[0201] Example 4

[0202] This embodiment provides an anthracene compound, and the specific synthesis route is as follows:

[0203]

[0204] Synthesis of intermediate 4-1:

[0205] The intermediate 9-bromo-10-(1-naphthyl)anthracene (3.8 g, 10 mmol) and 4-(4-bromonaphthyl)-1-naphthaleneboronic acid (2.5 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh 3 ) 4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain intermediate 4-1 by organic phase column chromatography and recrystallization. Yield: 63%. MS (ASAP) = 634.1.

[0206] Synthesis of compound 4:

[0207] Intermediate 4-1 (6.3 g, 10 mmol) and 1-6 (4.1 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh 3 ) 4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain compound 4 by organic phase column chromatography and recrystallization. Yield: 66%. MS (ASAP) = 838.3.

[0208] Example 5

[0209] This embodiment provides an anthracene compound, and the specific synthesis route is as follows:

[0210]

[0211] Synthesis of intermediate 5-1:

[0212] The intermediate 9-bromo-10-(1-naphthyl)anthracene (3.8 g, 10 mmol) and 10-bromo-9-anthraceneboronic acid (3.0 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh 3 ) 4(1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain intermediate 5-1 by column chromatography and recrystallization of the organic phase. Yield: 61%. MS (ASAP) = 558.1.

[0213] Synthesis of compound 5:

[0214] Intermediate 5-1 (5.6 g, 10 mmol) and 1-6 (4.1 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh 3 ) 4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain compound 5 by organic phase column chromatography and recrystallization. Yield: 52%. MS (ASAP) = 762.3.

[0215] Example 6

[0216] This embodiment provides an anthracene compound, and the specific synthesis route is as follows:

[0217]

[0218] Synthesis of intermediate 6-1:

[0219] The intermediate 9-bromo-10-(1-naphthyl)anthracene (3.8 g, 10 mmol) and 10-(4-bromo-1-naphthyl)-9-anthraceneboronic acid (4.3 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh 3 ) 4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain intermediate 6-1 by organic phase column chromatography and recrystallization. Yield: 64%. MS (ASAP) = 684.2.

[0220] Synthesis of compound 6:

[0221] Intermediate 6-1 (6.8 g, 10 mmol) and 1-6 (4.1 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh 3 ) 4(1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain compound 6 by organic phase column chromatography and recrystallization. Yield: 49%. MS (ASAP) = 888.3.

[0222] Example 7

[0223] This embodiment provides an anthracene compound, and the specific synthesis route is as follows:

[0224]

[0225] Synthesis of intermediate 7-1:

[0226] The intermediate 9-bromo-10-(1-naphthyl)anthracene (3.8 g, 10 mmol) and 2,3,4,6-tetramethyl-5-bromo-phenylboronic acid (2.6 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh 3 ) 4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain intermediate 7-1 by organic phase column chromatography and recrystallization. Yield: 44%. MS (ASAP) = 514.1.

[0227] Synthesis of compound 7:

[0228] Intermediate 7-1 (5.1 g, 10 mmol) and 1-6 (4.1 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh 3 ) 4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain compound 7 by organic phase column chromatography and recrystallization. Yield: 43%. MS (ASAP) = 718.3.

[0229] Example 8

[0230] This embodiment provides an anthracene compound, and the specific synthesis route is as follows:

[0231]

[0232] Synthesis of intermediate 8-1:

[0233] The intermediate 9-bromo-10-(1-naphthyl)anthracene (3.8 g, 10 mmol) and 4-(10-bromo-9-anthracenyl)-phenylboronic acid (3.8 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh 3 ) 4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain intermediate 8-1 by organic phase column chromatography and recrystallization. Yield: 49%. MS (ASAP) = 634.1.

[0234] Synthesis of compound 8:

[0235] Intermediate 8-1 (6.3 g, 10 mmol) and 1-6 (4.1 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh 3 ) 4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain compound 8 by organic phase column chromatography and recrystallization. Yield: 53%. MS (ASAP) = 838.3.

[0236] Example 9

[0237] This embodiment provides an anthracene compound, and the specific synthesis route is as follows:

[0238]

[0239] Synthesis of intermediate 9-1:

[0240] The intermediate 9-bromo-10-(1-naphthyl)anthracene (3.8 g, 10 mmol) and 2-methyl-4-bromo-naphthaleneboronic acid (2.6 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh 3 ) 4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain intermediate 9-1 by organic phase column chromatography and recrystallization. Yield: 77%. MS (ASAP) = 522.1.

[0241] Synthesis of compound 9:

[0242] Intermediate 9-1 (5.2 g, 10 mmol) and 1-6 (4.1 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh 3 ) 4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain compound 9 by organic phase column chromatography and recrystallization. Yield: 59%. MS (ASAP) = 726.3.

[0243] Example 10

[0244] This embodiment provides an anthracene compound, and the specific synthesis route is as follows:

[0245]

[0246] Synthesis of intermediate 10-1:

[0247] The intermediate 9-bromo-10-(1-naphthyl)anthracene (3.8 g, 10 mmol) and 2-methyl-4-(10-bromo-9-anthracenyl)-phenylboronic acid (3.9 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh 3 ) 4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain intermediate 9-1 by column chromatography and recrystallization of the organic phase. Yield: 52%. MS (ASAP) = 648.2.

[0248] Synthesis of compound 10:

[0249] Intermediate 10-1 (6.5 g, 10 mmol) and 1-6 (4.1 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh 3 ) 4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain compound 10 by organic phase column chromatography and recrystallization. Yield: 57%. MS (ASAP) = 852.3.

[0250] Embodiment 11

[0251] This embodiment provides an anthracene compound, and the specific synthesis route is as follows:

[0252]

[0253] Synthesis of intermediate 11-1:

[0254] Intermediate 1-3 (5 g, 17 mmol) and 2-fluoro-5-chlorophenylboronic acid pinacol ester (6.7 g, 26 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh 3 ) 4 (1.0 g, 0.87 mmol) and potassium carbonate (7.0 g, 51 mmol). Stir at 100 °C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash with water, and separate the liquid by organic phase column chromatography (eluent: DCM: PE = 1: 2) to obtain a white solid with a yield of 58%. MS (ASAP) = 338.1.

[0255] Synthesis of intermediate 11-2:

[0256] Intermediate 11-1 (5 g, 14.8 mmol) was dissolved in DMF (100 ml) solution, and potassium carbonate (10.2 g, 74 mmol) was added. Stir at 150 ° C for 12 h under nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then extracted with DCM and washed with water. The organic phase was column chromatographed (eluent: DCM: PE = 1: 5 (volume ratio)) to obtain a white solid with a yield of 38%. MS (ASAP) = 318.1.

[0257] Synthesis of intermediate 11-3:

[0258] Weigh 11-2 (5 g, 15.7 mmol), (Bpin) 2 (4.8g,18.8mmol), AcOK(9.8g,100mmol), Pd(dppf)Cl 2 (0.74 g, 1.0 mmol), t-Bu 3 P (0.39 g, 1.94 mmol) was placed in a 250 mL three-necked flask, 100 ml of 1,4-dioxane was added, nitrogen was replaced, and the reaction was carried out at 100°C for 12 h. The mixture was spin-dried, washed with water, and subjected to column chromatography (eluent: PE:DCM = 5:1 (volume ratio)) to obtain a colorless oily substance with a yield of 72%. MS (ASAP) = 410.2.

[0259] Synthesis of compound 11:

[0260] Intermediate 11-3 (4.1 g, 10 mmol) and 9-bromo-10-(1-naphthyl)anthracene (3.1 g, 12 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh 3 ) 4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain compound 11 by column chromatography and recrystallization of the organic phase. Yield: 55%. MS (ASAP) = 586.2.

[0261] Example 12

[0262] This embodiment provides an anthracene compound, and the specific synthesis route is as follows:

[0263]

[0264] Synthesis of intermediate 12-1:

[0265] The intermediate 9-bromo-10-(1-naphthyl)anthracene (3.8 g, 10 mmol) and 2-bromo-5-pyridineboronic acid (2.0 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh 3 ) 4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain intermediate 12-1 by organic phase column chromatography and recrystallization. Yield: 49%. MS (ASAP) = 459.1.

[0266] Synthesis of compound 12:

[0267] Intermediate 12-1 (4.6 g, 10 mmol) and 11-3 (4.1 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh 3 ) 4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain compound 12 by organic phase column chromatography and recrystallization. Yield: 38%. MS (ASAP) = 662.2.

[0268] Embodiment 13

[0269] This embodiment provides an anthracene compound, and the specific synthesis route is as follows:

[0270]

[0271] Synthesis of compound 13:

[0272] Intermediate 1-6 (4.1 g, 10 mmol) and 9-bromo-10-phenylanthracene (4.0 g, 12 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh 3 ) 4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain compound 13 by organic phase column chromatography and recrystallization. Yield: 53%. MS (ASAP) = 536.2.

[0273] Embodiment 14

[0274] This embodiment provides an anthracene compound, and the specific synthesis route is as follows:

[0275]

[0276] Synthesis of intermediate 14-1:

[0277] The intermediate 1,4-diphenylboronic acid pinacol ester (50 g, 151 mmol) and deuterated bromobenzene (24.4 g, 151 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (500 / 50 ml), and Pd(PPh 3 ) 4 (3.5 g, 3.0 mmol) and potassium carbonate (63 g, 454 mmol). Stir at 100 °C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash with water, and separate the liquid by organic phase column chromatography (eluent: DCM: PE = 1: 2) to obtain a white solid with a yield of 66%. MS (ASAP) = 285.2.

[0278] Synthesis of intermediate 14-2:

[0279] Intermediate 14-1 (10 g, 35 mmol) and 9,10-dibromoanthracene (18 g, 35 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (500 / 50 ml), and Pd(PPh 3 ) 4(0.8 g, 0.7 mmol) and potassium carbonate (24 g, 175 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain a white solid by organic phase column chromatography (eluent: PE), with a yield of 53%. MS (ASAP) = 413.1.

[0280] Synthesis of compound 14:

[0281] Intermediate 14-2 (4.1 g, 10 mmol) and 1-6 (4.1 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh 3 ) 4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain compound 14 by organic phase column chromatography and recrystallization. Yield: 72%. MS (ASAP) = 617.2.

[0282] Embodiment 15

[0283] This embodiment provides an anthracene compound, and the specific synthesis route is as follows:

[0284]

[0285] Synthesis of intermediate 15-1:

[0286] Dibenzothiophene-1-boric acid (2.3 g, 10 mmol) and 9,10-dibromoanthracene (3.4 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh 3 ) 4 (1.5 g, 1 mmol) and potassium carbonate (6.9 g, 50 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain a white solid by organic phase column chromatography (eluent: PE), with a yield of 77%. MS (ASAP) = 440.0.

[0287] Synthesis of compound 15:

[0288] Intermediate 15-1 (4.4 g, 10 mmol) and 1-6 (4.1 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh 3 ) 4(1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain compound 15 by organic phase column chromatography and recrystallization. Yield: 52%. MS (ASAP) = 642.2.

[0289] Example 16

[0290] This embodiment provides an anthracene compound, and the specific synthesis route is as follows:

[0291]

[0292] Synthesis of intermediate 16-1:

[0293] Dibenzofuran-2-boric acid (2.1 g, 10 mmol) and 9,10-dibromoanthracene (3.4 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh 3 ) 4 (1.5 g, 1 mmol) and potassium carbonate (6.9 g, 50 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain a white solid by organic phase column chromatography (eluent: PE), with a yield of 72%. MS (ASAP) = 422.0.

[0294] Synthesis of compound 16:

[0295] Intermediate 16-1 (4.2 g, 10 mmol) and 1-6 (4.1 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh 3 ) 4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain compound 16 by organic phase column chromatography and recrystallization. Yield: 59%. MS (ASAP) = 626.2.

[0296] Embodiment 17

[0297] This embodiment provides an anthracene compound, and the specific synthesis route is as follows:

[0298]

[0299] Synthesis of intermediate 17-1:

[0300] Fluoranthene-3-boric acid (2.5 g, 10 mmol) and 9,10-dibromoanthracene (3.4 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh 3 ) 4 (1.5 g, 1 mmol) and potassium carbonate (6.9 g, 50 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash with water, separate the liquid, and obtain a white solid by organic phase column chromatography (eluent: PE), with a yield of 76%. MS (ASAP) = 456.1.

[0301] Synthesis of compound 17:

[0302] Intermediate 17-1 (4.2 g, 10 mmol) and 1-6 (4.1 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh 3 ) 4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol). Stir at 100°C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain compound 17 by organic phase column chromatography and recrystallization. Yield: 71%. MS (ASAP) = 660.2.

[0303] Preparation of OLED devices

[0304] The compound structures involved in preparing OLED devices are:

[0305]

[0306] The following is a detailed description of the preparation process of the OLED-1 device using the above compounds through a specific embodiment. The structure of the OLED device is: ITO / HIL / HTL / EML / ETL / cathode. The schematic diagram of the OLED device is shown in FIG. Figure 1 As shown, 101 is a substrate, 102 is an anode, 103 is a hole injection layer (HIL), 104 is a hole transport layer (HTL), 105 is a light emitting layer, 106 is an electron transport layer (ETL), and 107 is a cathode.

[0307] The preparation steps of OLED-1 are as follows:

[0308] a. Cleaning of ITO (indium tin oxide) conductive glass substrates: using various solvents (such as one or more of chloroform, acetone or isopropyl alcohol) for cleaning, followed by ultraviolet ozone treatment;

[0309] b. HIL (hole injection layer, 40nm): 60nm PEDOT (polyethylenedioxythiophene, Clevios TM AI4083) was spin-coated as HIL in a clean room and treated on a hot plate at 180 °C for 10 min;

[0310] c. HTL (hole transport layer, 20 nm): 20 nm of PVK (Sigma Aldrich, average Mn 25,000-50,000) was prepared by spin coating in a nitrogen glove box. The solution used was PVK added to toluene solvent at a concentration of 5 mg / ml, followed by treatment on a hot plate at 180 °C for 60 min.

[0311] d. EML (organic light-emitting layer, 40 nm): EML was formed by spin coating in a nitrogen glove box. The solution used was a methyl benzoate solution of different host and guest (the weight ratio of host and guest was 95:5), and the solution solubility was 15 mg / ml. It was then treated on a hot plate at 140° C. for 10 minutes. The host used compound 1 of Example 1, and the guest material was selected from BD-1.

[0312] e. Electron transport layer and cathode: The heat-treated substrate was transferred to a vacuum chamber, and then ET and Liq were placed in different evaporation units and co-deposited in a high vacuum (1×10-6 mbar) at a ratio of 50 wt %, respectively, to form a 20 nm electron transport layer on the light-emitting layer, followed by depositing an Al cathode with a thickness of 100 nm.

[0313] f. Packaging: The device is packaged with UV-curable resin in a nitrogen glove box.

[0314] The implementation schemes of OLED-2 to OLED-17 and OLED-Ref are the same as OLED1, except that the compound 1 in OLED-1 is replaced by the compound corresponding to the host material in Table 1.

[0315] The current-voltage (JV) characteristics of each OLED device were characterized using a characterization apparatus, while important parameters such as efficiency, lifetime, and external quantum efficiency were recorded. The results are shown in Table 1.

[0316] Table 1

[0317] Device Embodiment Main material CE@1knits[cd / A] LT90@1knits[h] OLED-1 Compound 1 5.1 390 OLED-2 Compound 2 5.3 392 OLED-3 Compound 3 5.9 377 OLED-4 Compound 4 5.8 387 OLED-5 Compound 5 5.7 372 OLED-6 Compound 6 5.9 369 OLED-7 Compound 7 6.2 393 OLED-8 Compound 8 5.9 374 OLED-9 Compound 9 5.8 367 OLED-10 Compound 10 5.3 347 OLED-11 Compound 11 5.3 324 OLED-12 Compound 12 5.6 373 OLED-13 Compound 13 6.1 392 OLED-14 Compound 14 6.6 401 OLED-15 Compound 15 6.7 403 OLED-16 Compound 16 6.9 414 OLED-17 Compound 17 5.4 389 OLED-Ref BH-ref 4.9 289

[0318] After testing, the life and luminescence of the blue light device prepared by using compound 1-compound 17 as the main material in the EML layer light-emitting layer are better than the device comparison. For the device OLED-15, 16, more hole transport groups are introduced into the molecule, so that the device reaches a more ideal electrical balance state, thereby improving the device performance. For the device OLED-14, the molecule is partially deuterated, which increases the molecular stability and improves the overall device performance.

[0319] The technical features of the above-described embodiments may be arbitrarily combined. To make the description concise, not all possible combinations of the technical features in the above-described embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0320] The above-described embodiments only express several implementation methods of the present invention, which are convenient for understanding the technical solutions of the present invention in detail, but they cannot be understood as limiting the scope of protection of the invention patent. It should be pointed out that, for ordinary technicians in this field, several variations and improvements can be made without departing from the concept of the present invention, which all belong to the protection scope of the present invention. It should be understood that the technical solutions obtained by those skilled in the art through logical analysis, reasoning or limited experiments on the basis of the technical solutions provided by the present invention are all within the protection scope of the claims attached to the present invention. Therefore, the protection scope of the patent of the present invention shall be based on the contents of the attached claims, and the description can be used to interpret the contents of the claims.

Claims

1. An anthracene compound, characterized in that: The structure of the anthracene compound is selected from any one of the structures shown in general formulas (2-1) to (2-4): ； in: L1 is selected from a single bond or any of the following groups: ； L2 is selected from a single bond or ; Each occurrence of X is independently selected from CR4, and each occurrence of R4 is independently selected from H and D; Y is selected from O, S; m1, m2 and m3 are 0; * indicates the attachment site.

2. The anthracene compound according to claim 1, characterized in that The structure of the anthracene compound is selected from the general formula (3-1) or (3-2): 。 3. The anthracene compound according to claim 1, characterized in that The anthracene compound is selected from the following structures: 。 4. A mixture, characterized in that The mixture comprises the anthracene compound according to any one of claims 1 to 3, and at least one organic functional material, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminophores or host materials.

5. A composition, characterized in that The composition comprises the anthracene 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, characterized in that: The organic electronic device comprises a first electrode, a second electrode, and one or more organic functional layers located between the first electrode and the second electrode, the organic functional layer comprises a light-emitting layer, the light-emitting layer comprises the anthracene compound according to any one of claims 1 to 3, or the light-emitting layer comprises the mixture according to claim 4, or the light-emitting layer is prepared from the composition according to claim 5.

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