Organic Electroluminescent Devices and Their Applications

Abstract

The present invention relates to the field of organic electroluminescence technology, and in particular, to an organic electroluminescent device and its application. The present invention provides an organic electroluminescent device, which comprises: a cathode, an anode, and one or more organic functional layers located between the cathode and the anode. The organic functional layer at least comprises a light-emitting layer, and the light-emitting layer material comprises a host material and a guest material. The guest material has a structure represented by formula (I) or formula (II), and the host material has a structure represented by formula (III). The organic electroluminescent device provided by the present invention has relatively high luminous efficiency and long service life.

Description

Technical Field

[0001] The present invention relates to the technical field of organic electroluminescence, and particularly relates to an organic electroluminescent device and its application. Background Art

[0002] Due to the diversity in synthesis, relatively low manufacturing cost, and excellent optical and electrical properties of organic semiconductor materials, organic light-emitting diodes (OLEDs) have great potential in the applications of optoelectronic devices (such as flat panel displays and lighting).

[0003] The organic electroluminescence phenomenon refers to the phenomenon of converting electrical energy into light energy using organic substances. An organic electroluminescent element utilizing the organic electroluminescence phenomenon usually has a structure including a positive electrode and a negative electrode, and an organic layer between them. To improve the efficiency and lifespan of the organic electroluminescent element, the organic layer has a multi-layer structure, and each layer contains different organic substances. Specifically, it may 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 electroluminescent element, when a voltage is applied between the two electrodes, holes are injected from the positive electrode into the organic layer, and electrons are injected from the negative electrode into the organic layer. When the injected holes and electrons meet, excitons are formed, and light is emitted when the excitons transition back to the ground state. Such an organic electroluminescent element has characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high responsiveness.

[0004] To improve the luminous efficiency of organic electroluminescent elements, various luminescent material systems based on fluorescence and phosphorescence have been developed. However, for both fluorescent materials and phosphorescent materials, the development of excellent blue light materials is a huge challenge. Generally speaking, the organic light-emitting diodes using current blue fluorescent materials have higher reliability. Nevertheless, the efficiency of most current blue fluorescent materials is relatively low, which is not conducive to high-end displays. At the same time, the stability and lifespan of OLEDs using such blue fluorescent materials still need to be further improved. Summary of the Invention

[0005] Based on this, the present invention provides an organic electroluminescent device and its application, aiming to improve the luminous efficiency and lifespan of the organic electroluminescent device.

[0006] On one hand, the present invention provides an organic electroluminescent device, which includes: a cathode, an anode, and one or more organic functional layers located between the cathode and the anode. The organic functional layer at least includes a light-emitting layer. The material of the light-emitting layer includes a host material and a guest material. The guest material has a structure shown in formula (I) or formula (II), and the host material has a structure shown in formula (III):

[0007]

[0008] Among them, Ar 1 ~Ar 7 are each independently selected from substituted or unsubstituted aryl having 6 to 40 ring atoms, or substituted or unsubstituted heteroaryl having 5 to 40 ring atoms;

[0009] Each occurrence of X is independently selected from CR 1 or N;

[0010] Each occurrence of Z is independently selected from NR 2 , PR 2 , CR 3 R 4 , SiR 3 R 4 , O, S, S(=O) 2 or S=O;

[0011] R 1 ~R 4 Each occurrence is independently selected from: -H, -D, linear alkyl having 1 to 20 C atoms, branched alkyl or cycloalkyl having 3 to 20 C atoms, alkoxy or thioalkoxy having 1 to 20 C atoms, branched alkoxy or cycloalkoxy having 3 to 20 C atoms, branched thioalkoxy having 3 to 20 C atoms, cyclic thioalkoxy having 3 to 20 C atoms, silyl, keto group having 1 to 20 C atoms, alkoxycarbonyl having 2 to 20 C atoms, aryloxycarbonyl having 7 to 20 C atoms, cyano, carbamoyl, halocarbonyl, formyl, isocyano, isocyanate group, thiocyanate group, isothiocyanate group, hydroxy, nitro, amino, -CF 3 , -OCF 3 , -Cl, -Br, -F, substituted or unsubstituted aryl having 5 to 40 ring atoms, substituted or unsubstituted heteroaryl having 5 to 40 ring atoms, substituted or unsubstituted aryloxy having 5 to 40 ring atoms, and substituted or unsubstituted heteroaryloxy having 5 to 40 ring atoms, and two adjacent R 1 optionally form or do not form an aliphatic ring system, an aromatic ring system, or a heteroaromatic ring system with each other;

[0012]

[0013] Among them, Ar 8 ~Ar 10 are each independently selected from substituted or unsubstituted aryl having 6 to 40 ring atoms, or substituted or unsubstituted heteroaryl having 5 to 40 ring atoms.

[0014] Beneficial effects

[0015] Through research, it is found in the present invention that the guest material of the BN structure represented by formula (I) or formula (II) has a high exciton utilization rate; the host material of the BO structure represented by formula (III) has a high triplet energy level and can effectively transfer the energy of excitons to the guest material, which can effectively improve the energy utilization efficiency of the device. On the other hand, both the host of the BO structure and the guest of the BN structure are planar skeletons, which is conducive to light extraction and energy transfer, and can further improve the luminescence efficiency and lifespan of the device. Detailed Embodiments

[0016] To facilitate the understanding of the present invention, the present invention will be described more comprehensively below. However, the present invention can be implemented in many different forms and is not limited to the embodiments described herein. On the contrary, these embodiments are provided to make the understanding of the disclosure of the present invention more thorough and comprehensive.

[0017] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the technical field to which the present invention belongs. The terms used in the description of the present invention herein 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 of the related listed items.

[0018] Terms and Definitions

[0019] In the present invention, "substituted" means that a hydrogen atom in the substituent is replaced by a substituent.

[0020] In the present invention, when the same substituent appears multiple times, it can be independently selected from different groups. For example, if the general formula contains multiple Rs 1 , then R 1 can be independently selected from different groups.

[0021] In the present invention, "substituted or unsubstituted" means that the defined group can be substituted or unsubstituted. When the defined group is substituted, it should be understood that it is optionally substituted by a group acceptable in the art, including but not limited to: deuterium atom, cyano group, isocyano group, nitro group, halogen atom, C 1-10 alkyl, C 1-10 alkoxy, C 1-10 alkylthio, C 6-30 aryl, C 6-30 aryloxy, C 6-30 arylthio, C 3-30 heteroaryl, C 1-30 silyl, C 2-10 alkylamino, C 6-30 arylamino, or a combination of the above groups, etc.

[0022] In the present invention, "the number of ring atoms" refers to the number of atoms among the atoms constituting the ring itself in a structural compound obtained by bonding atoms into a ring (for example, a monocyclic compound, a fused-ring compound, a crosslinked compound, a carbocyclic compound, a heterocyclic compound). When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to "the number of ring atoms" described below unless otherwise specified. For example, the number of ring atoms in a benzene ring is 6, the number of ring atoms in a naphthalene ring is 10, and the number of ring atoms in a thienyl group is 5.

[0023] In the present invention, "alkyl" may represent a straight-chain, branched-chain, and / or cyclic alkyl. The number of carbon atoms in the alkyl may be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. A phrase containing this term, for example, "C 1-9 alkyl" refers to an alkyl containing 1 to 9 carbon atoms, and each occurrence may independently be 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 9 alkyl. Non-limiting examples of the alkyl 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, n-triacontyl, adamantane, etc.

[0024] "Aryl or aromatic group" refers to an aromatic hydrocarbon group derived by removing one hydrogen atom from an aromatic ring compound, and may be a monocyclic aryl, a fused-ring aryl, or a polycyclic aryl. For a polycyclic ring species, at least one is an aromatic ring system. For example, "aryl having 6 to 40 ring atoms, which may be substituted or unsubstituted" refers to an aryl containing 6 to 40 ring atoms, preferably aryl having 6 to 30 ring atoms, which may be substituted or unsubstituted, more preferably aryl having 6 to 18 ring atoms, which may be substituted or unsubstituted, and particularly preferably aryl having 6 to 14 ring atoms, and the aryl may optionally be further substituted; suitable examples include, but are not limited to: benzene, biphenyl, terphenyl, naphthalene, anthracene, fluoranthene, phenanthrene, benzo[a]phenanthrene, dibenzo[a,h]anthracene, tetracene, pyrene, benzo[a]pyrene, acenaphthene, fluorene, and their derivatives. It is understood that multiple aryl groups may also be interrupted by short non-aromatic units (for example, <10% non-H atoms, such as C, N, or O atoms), specifically such as acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aryl.

[0025] "Heteroaryl or heteroaromatic group" means that on the basis of an aryl group, at least one carbon atom is replaced by a non-carbon atom, 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 substituted or unsubstituted heteroaryl having 6 to 30 ring atoms, more preferably substituted or unsubstituted heteroaryl having 6 to 18 ring atoms, particularly preferably substituted or unsubstituted heteroaryl having 6 to 14 ring atoms, and the heteroaryl is optionally further substituted. Suitable examples include but are not limited to: triazine, pyridine, pyrimidine, imidazole, furan, thiophene, benzofuran, benzothiophene, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thiophenopyrrole, thiophenothiophene, furanopyrrole, furanofuran, thiophenofuran, benzisoxazole, benzisothiazole, benzimidazole, quinoline, isoquinoline, phthalazine, quinoxaline, phenanthridine, peridine, quinazoline, quinazolinone, dibenzothiophene, dibenzofuran, carbazole and their derivatives.

[0026] "Amino group" means a derivative of an amine having the structural feature of the formula -N(X) 2 , where each "X" is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclic group, etc. Non-limiting types of amino groups include -NH 2 , -N(alkyl) 2 , -NH(alkyl), -N(cycloalkyl) 2 , -NH(cycloalkyl), -N(heterocyclic group) 2 , -NH(heterocyclic group), -N(aryl) 2 , -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclic group), -N(cycloalkyl)(heterocyclic group), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0027] In the present invention, the "*" connected to a single bond represents a connection or fusion site.

[0028] In the present invention, when the connection site is not specified in the group, it means that any optional connection site in the group can be used as the connection site;

[0029] In the present invention, when the fusion site is not specified in the group, it means that any optional fusion site in the group can be used as the fusion site, and preferably two or more sites adjacent to each other in the group are used as the fusion site;

[0030] In the present invention, the single bond to which the substituent is connected passes through the corresponding ring, indicating that the substituent can be connected to any optional position of the ring. For example in R is connected to any substitutable site of the benzene ring, such as in, Fused to any fusible site of the benzene ring.

[0031] In the present invention, "adjacent groups" means that there is no substitutable site between two substituents.

[0032] In one aspect of the present invention, there is provided an organic electroluminescent device, which comprises: a cathode, an anode, and one or more organic functional layers located between the cathode and the anode, the organic functional layer at least comprising a light-emitting layer, the light-emitting layer material comprising a host material and a guest material, the guest material having a structure represented by formula (I) or formula (II), and the host material having a structure represented by formula (III):

[0033]

[0034] Wherein, Ar 1 ~Ar 7 Are each independently selected from a substituted or unsubstituted aryl group having 6 to 40 ring atoms, or a substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms;

[0035] Each occurrence of X is independently selected from CR 1 Or N;

[0036] Each occurrence of Z is independently selected from NR 2 , PR 2 , CR 3 R 4 , SiR 3 R 4 , O, S, S(=O) 2 Or S=O;

[0037] R 1 ~R 4 Each occurrence is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 20 C atoms, a branched-chain alkyl group or cycloalkyl group having 3 to 20 C atoms, an alkoxy group or thioalkoxy group having 1 to 20 C atoms, a branched-chain alkoxy group or cycloalkoxy group having 3 to 20 C atoms, a branched-chain thioalkoxy group having 3 to 20 C atoms, a cyclic thioalkoxy group having 3 to 20 C atoms, a silyl group, a ketone 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 halocarbonyl 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 , -OCF 3, -Cl, -Br, -F, a substituted or unsubstituted aryl having 5 to 40 ring atoms, a substituted or unsubstituted heteroaryl having 5 to 40 ring atoms, a substituted or unsubstituted aryloxy having 5 to 40 ring atoms, and a substituted or unsubstituted heteroaryloxy having 5 to 40 ring atoms, one or more of which, two adjacent Rs 1 optionally form or do not form an aliphatic ring system, an aromatic ring system, or a heteroaromatic ring system with each other;

[0038]

[0039] wherein, Ar 8 ~Ar 10 each independently selected from a substituted or unsubstituted aryl having 6 to 40 ring atoms, or a substituted or unsubstituted heteroaryl having 5 to 40 ring atoms.

[0040] In one embodiment, each occurrence of X is independently selected from CR 1 ;

[0041] R 1 each occurrence is independently selected from: -H, -D, a straight-chain alkyl having 1 to 10 C atoms, a branched-chain alkyl having 3 to 10 C atoms, a cyclic alkyl having 3 to 10 C atoms, a substituted or unsubstituted aryl having 5 to 20 ring atoms, and a substituted or unsubstituted heteroaryl having 5 to 20 ring atoms.

[0042] Furthermore, each occurrence of R 1 is independently selected from: -H, -D, a straight-chain alkyl having 1 to 8 C atoms, or a branched-chain alkyl having 3 to 8 C atoms.

[0043] Even further, at least one R 1 is selected from a straight-chain alkyl having 1 to 8 C atoms or a branched-chain alkyl having 3 to 8 C atoms.

[0044] Still further, at least one R 1 is selected from methyl, n is any integer between 0 and 4, and the R 1 can be further substituted by D;

[0045] When n is selected as 0, R 1 is selected from methyl,

[0046] In one embodiment, Ar 1 ~Ar 10 each independently selected from a substituted or unsubstituted aryl having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaryl having 6 to 25 ring atoms.

[0047] Further, Ar 1 ~Ar 10 are each independently selected from a substituted or unsubstituted aryl having 6 to 13 ring atoms, or a substituted or unsubstituted heteroaryl having 6 to 13 ring atoms.

[0048] In one embodiment, Ar 1 ~Ar 10 are each independently selected from any one of the groups (B-1) to (B-12):

[0049]

[0050] Wherein, X 1 each occurrence is independently selected from CR 5 or N; when X 1 is a linking site, X 1 is selected from C;

[0051] Y each occurrence is independently selected from NR 6 、PR 6 、CR 7 R 8 、SiR 7 R 8 、O、S、S(=O) 2 or S=O;

[0052] R 5 ~R 8 each occurrence is independently selected from: -H, -D, a straight-chain alkyl having 1 to 20 C atoms, an alkoxy having 1 to 20 C atoms, a thioalkoxy having 1 to 20 C atoms, a branched-chain alkyl having 3 to 20 C atoms, a cycloalkyl having 3 to 20 C atoms, a branched-chain alkoxy having 3 to 20 C atoms, a cycloalkoxy having 3 to 20 C atoms, a branched-chain thioalkoxy having 3 to 20 C atoms, a cyclo thioalkoxy having 3 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl having 2 to 20 C atoms, an aryloxycarbonyl having 7 to 20 C atoms, a cyano group, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, -CF 3 、-OCF 3 、-Cl、-Br、-F, a substituted or unsubstituted aryl having 5 to 40 ring atoms, a substituted or unsubstituted heteroaryl having 5 to 40 ring atoms, a substituted or unsubstituted aryloxy having 5 to 40 ring atoms, and a substituted or unsubstituted heteroaryloxy having 5 to 40 ring atoms, and two adjacent R 5Optionally, they form or do not form an aliphatic ring system, an aromatic ring system, or a heteroaromatic ring system with each other.

[0053] In one embodiment, Ar 1 ~Ar 7 are each independently selected from any one of the following structures:

[0054]

[0055] wherein, * represents the fusion site.

[0056] In some embodiments, in formula (I), at least one of Ar 1 ~Ar 3 is selected from formula (B-2); further, Ar 2 is selected from (B-2).

[0057] In some embodiments, in formula (I), at least two of Ar 1 ~Ar 3 are selected from formula (B-2); further, Ar 2 and Ar 3 are selected from (B-2).

[0058] In some embodiments, in formula (I), all of Ar 1 ~Ar 3 are selected from formula (B-2).

[0059] In some embodiments, in formula (I), at least one of Ar 1 ~Ar 3 is selected from formula (B-2), and at least one other is selected from formula (B-6). Further, any two of Ar 1 ~Ar 3 are selected from formula (B-2), and the other is selected from formula (B-6).

[0060] In some embodiments, in formula (I), at least one of Ar 1 ~Ar 3 is selected from formula (B-2), and at least one other is selected from formula (B-4). Further, any two of Ar 1 ~Ar 3 are selected from formula (B-2), and the other is selected from formula (B-4).

[0061] In some embodiments, in formula (I), at least one of Ar 1 ~Ar 3 is selected from formula (B-2), and at least one other is selected from formula (B-3). Further, any two of Ar 1 ~Ar 3Any two of them are each independently selected from formula (B-2), and the other is selected from formula (B-3).

[0062] In some embodiments, in formula (I), Ar 1 ~Ar 3 At least one of them is selected from formula (B-2), and at least another one is selected from formula (B-7). Further, Ar 1 ~Ar 3 Any two of them are each independently selected from formula (B-2), and the other is selected from formula (B-7).

[0063] In some embodiments, in formula (I), Ar 1 ~Ar 3 At least one of them is selected from formula (B-2), and at least another one is selected from formula (B-9). Further, Ar 1 ~Ar 3 Any two of them are each independently selected from formula (B-2), and the other is selected from formula (B-9).

[0064] In a preferred embodiment, Ar 1 is selected from (B-4). Further, Ar 2 is selected from (B-2). Still further, Ar 3 is selected from (B-2), (B-3) or (B-6). The reason is that introducing heteroatoms into the framework of the structure near the B atom can better adjust the optoelectronic properties of the molecule.

[0065] In a preferred embodiment, Ar 1 is selected from (C-5). Further, Ar 2 is selected from (C-2).

[0066] In one embodiment, the compound of formula (II) is a symmetric structure compound.

[0067] In one embodiment, Ar 4 and Ar 7 in formula (II) are each independently selected from (B-2)-(B-6); further, Ar 4 and Ar 7 are selected from the same group; still further, Ar 4 and Ar 7 are selected from

[0068] In one embodiment, Ar 5 and Ar 6 in formula (II) are each independently selected from (B-2)-(B-6); further, Ar 5 and Ar 6 are selected from the same group; still further, Ar 5 and Ar 6Selected from

[0069] In one embodiment, Ar 4 and Ar 7 are simultaneously selected from or Ar 5 and Ar 6 are simultaneously selected from

[0070] In one embodiment, formula (I) is selected from any one of formula (4-1) to formula (4-16):

[0071]

[0072]

[0073] Further, Z is selected from NR 2 , CR 3 R 4 , O or S; still further, Z is selected from NR 2 ; wherein, R 2 is 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 cyclic alkyl group having 3 to 10 C atoms, an aromatic group having 5 to 20 ring atoms, a heteroaromatic group having 5 to 20 ring atoms, an aromatic group having 5 to 20 ring atoms substituted by a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms or a cycloalkyl group having 3 to 10 C atoms, a heteroaromatic group having 5 to 20 ring atoms substituted by a branched-chain alkyl group having 3 to 10 C atoms or a cyclic alkyl group having 3 to 10 C atoms.

[0074] In some of these embodiments, R 2 is 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, an aromatic group having 5 to 20 ring atoms, a heteroaromatic group having 5 to 20 ring atoms, an aromatic group having 5 to 20 ring atoms substituted by a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms or a cycloalkyl group having 3 to 10 C atoms, a heteroaromatic group having 5 to 20 ring atoms substituted by a branched-chain alkyl group having 3 to 10 C atoms or a cyclic alkyl group having 3 to 10 C atoms.

[0075] Further, R 2 is selected from -H, -D, a straight-chain alkyl group having 1 to 5 C atoms, a branched-chain alkyl group having 3 to 10 C atoms or the following structures:

[0076]

[0077] wherein, R 10 each occurrence is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 10 C atoms, an aromatic group having 5 to 20 ring atoms, a heteroaromatic group having 5 to 20 ring atoms, an aromatic group having 5 to 20 ring atoms substituted by a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms or a cycloalkyl group having 3 to 10 C atoms, or a heteroaromatic group having 5 to 20 ring atoms substituted by a branched-chain alkyl group having 3 to 10 C atoms or a cycloalkyl group having 3 to 10 C atoms;

[0078] n 3 is any integer selected from 1 - 4.

[0079] In some embodiments, n 3 is any integer selected from 1 - 3.

[0080] In some embodiments, n 3 is selected from 1; in other embodiments, n 3 is selected from 2.

[0081] In one embodiment, R 10 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 5 C atoms, an aromatic group having 5 to 10 ring atoms, a heteroaromatic group having 5 to 10 ring atoms; further, R 10 is independently selected from: -H, -D, methyl, isopropyl, tert-butyl or phenyl.

[0082] In one embodiment, formula (II) is selected from any one of formulas (5-1) to (5-13):

[0083]

[0084]

[0085] In one embodiment, in formula (I), formula (II), formulas (4-1) to (4-16) or formulas (5-1) to (5-13), X 1 each occurrence is independently selected from CR 5 ; R 5 each occurrence is independently selected from at least one of: -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 cyclic alkyl group having 3 to 10 C atoms, a substituted or unsubstituted aryl group having 5 to 20 ring atoms, and a substituted or unsubstituted heteroaryl group having 5 to 20 ring atoms.

[0086] Further, R5 Each occurrence is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 8 carbon atoms, or a branched-chain alkyl group having 3 to 8 carbon atoms.

[0087] Furthermore, at least one R 5 is selected from a straight-chain alkyl group having 1 to 8 carbon atoms or a branched-chain alkyl group having 3 to 8 carbon atoms.

[0088] Still further, at least one R 5 is selected from methyl, n is any integer between 0 and 4; the R 5 can be further substituted by D.

[0089] In one embodiment, when Ar 1 ~Ar 7 is selected from formula (C-2), formula (C-2) is selected from the following structures:

[0090]

[0091] wherein, R 5 has the same meaning as described above. Further, (C-2) is selected from the following structures:

[0092]

[0093] In one embodiment, formula (I) and formula (II) respectively have the following general formulas:

[0094]

[0095] Preferably, in formula (1) or formula (2), R 1 are independently selected from: methyl, n is any integer between 0 and 4.

[0096] In one embodiment, formula (III) has the following general formula:

[0097]

[0098] Further, Ar 9 ~Ar 10 are each independently selected from any one of the groups (B-2) to (B-6).

[0099] In one embodiment, Ar 9 ~Ar 10 are each independently selected from the following structures:

[0100]

[0101] In one embodiment, Formula (III) is selected from any one of the following general formulas (6-1)-(6-8):

[0102]

[0103] In one embodiment, in Formula (3-1) or Formulas (6-1) to (6-8), X 1 each occurrence is independently selected from CR 5 ; preferably, at least one R 5 is selected from aryl or heteroaryl having 6 to 20 ring atoms.

[0104] Furthermore, Formula (III) is selected from any one of the general formulas (7-1) to (7-8):

[0105]

[0106] Preferably, in Formulas (7-1) to (7-8), R 5 is selected from aryl or heteroaryl having 6 to 20 ring atoms. Furthermore, in Formulas (7-1) to (7-8), R 5 is selected from the following general formulas:

[0107]

[0108] wherein, L 1 is selected from a single bond, phenyl, biphenyl, terphenyl or naphthyl; Y 1 has the same meaning as that described for Y.

[0109] Even further, in Formulas (7-1) to (7-8), R 5 is selected from the following groups:

[0110]

[0111] In one embodiment, for the organic electroluminescent device according to the present invention, the host material is selected from:

[0112]

[0113] The guest material is selected from Formula (4-2), (5-2) or (5-10).

[0114] In the present invention, the host material may be selected from the following structures, but is not limited thereto:

[0115]

[0116]

[0117]

[0118] In the present invention, the guest material may be selected from the following structures, but is not limited thereto:

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125] In one embodiment, H in the structure of the guest material of the present invention may be partially deuterated. Preferably, 10% of H is deuterated, more preferably 20% of H is deuterated, still more preferably 30% of H is deuterated, and most preferably 40% of H is deuterated.

[0126] Furthermore, the above-mentioned organic functional layer is a light-emitting layer, which includes a host material and a guest material, and the guest material is the above-mentioned guest material or a mixture; still further, the mass ratio range of the host material to the guest material is 90:10 to 99:1; still further, the mass ratio range of the host material to the guest material is 80:20 to 99:1.

[0127] In one embodiment, the organic multi-functional layer further includes at least one layer of an electron injection layer, an electron transport layer, an electron blocking layer, a hole injection layer, a hole transport layer, and a hole blocking layer. Materials suitable for preparing the hole injection layer, the hole transport layer, the electron blocking layer, the electron injection layer, the electron transport layer, and the hole blocking layer can be found in the following patent documents: WO2010135519A1, US20090134784A1, and WO2011110277A1. The entire contents of the above-listed patent documents are hereby incorporated herein by reference.

[0128] In some embodiments, the organic multi-functional layer includes a hole transport layer, a light-emitting layer, and an electron transport layer.

[0129] In other embodiments, the organic multi-functional layer includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.

[0130] In one embodiment, the organic electroluminescent device further includes a light extraction layer, and the light extraction layer is located on the electrode surface and on the side away from the organic functional layer; further, the light extraction layer is located on the cathode surface.

[0131] In one embodiment, the organic multi-functional layer is prepared by vacuum evaporation, coating or printing.

[0132] Further, the coating method includes at least one of dip coating, spin coating, blade coating, spraying, brush coating and slot die coating.

[0133] Further, the printing method includes at least one of inkjet printing, inkjet printing, letterpress printing, screen printing, roller printing, reverse roller printing, lithography, flexography, gravure printing, rotary printing and pad printing. In some embodiments, the printing method is at least one of gravure printing, inkjet printing and inkjet printing.

[0134] The organic electroluminescent device of the present invention may be selected from an organic light emitting diode, an organic photovoltaic cell, an organic light emitting cell, an organic field effect transistor, an organic light emitting field effect transistor, an organic laser, an organic spintronic device, an organic sensor or an organic plasmonic emission diode. Preferably, the organic electroluminescent device of the present invention is selected from an organic light emitting diode (OLED).

[0135] In the above-mentioned organic electroluminescent device, especially in the OLED, it includes a substrate, an anode, a cathode and at least one light emitting layer located between the anode and the cathode.

[0136] Further, the substrate may be opaque or transparent. A transparent substrate can be used to manufacture a transparent light emitting component. For example, see Bulovic et al. Nature (1996), 380, p29, Gu et al. Appl. Phys. Lett. (1996), 68, p2606. The entire content of the above-mentioned documents is hereby incorporated herein by reference.

[0137] Further, the substrate may be rigid or flexible.

[0138] Furthermore, the substrate may be a polymer, a metal, a semiconductor wafer or glass. Preferably, the substrate has a smooth surface, and a substrate without surface defects is a particularly ideal choice; furthermore, the substrate is flexible and may be selected from polymer films, and its glass transition temperature Tg≥150°C, preferably Tg>200°C, more preferably Tg>250°C, most preferably Tg>300°C.

[0139] Examples of suitable flexible substrates are poly(ethylene terephthalate) (PET) and poly(ethylene 2,6-naphthalate) (PEN).

[0140] The anode includes a conductive metal, a metal oxide or a conductive polymer. The anode can easily inject holes into the hole injection layer (HIL), the hole transport layer (HTL) or the light emitting layer.

[0141] In one 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 serving as the HIL, HTL, or electron blocking layer (EBL) is < 0.5 eV, preferably < 0.3 eV, and most preferably < 0.2 eV.

[0142] Furthermore, the anode material includes, but is not limited to: Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO).

[0143] In some embodiments, the anode is pattern-structured.

[0144] The cathode includes a conductive metal or metal oxide. The cathode can easily inject electrons into the electron injection layer (EIL), the electron transport layer (ETL), or directly into the light-emitting layer.

[0145] In one 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 the n-type semiconductor material serving as the EIL, ETL, or hole blocking layer (HBL) is < 0.5 eV, preferably < 0.3 eV, and most preferably < 0.2 eV.

[0146] In one embodiment, the cathode material includes, but is not limited to: Al, Au, Ag, Ca, Ba, Mg, LiF / Al, Mg / Ag alloy, BaF 2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO.

[0147] In the present invention, the anode material and the cathode material can be deposited using any suitable technique, such as physical vapor deposition; furthermore, physical vapor deposition includes radio frequency magnetron sputtering, vacuum thermal evaporation, or electron beam (e-beam).

[0148] In one embodiment, the emission wavelength of the organic electroluminescent device is between 300 nm and 1000 nm; preferably, the emission wavelength of the organic electroluminescent device is between 350 nm and 900 nm; more preferably, the emission wavelength of the organic electroluminescent device is between 400 nm and 800 nm.

[0149] The present invention also relates to the application of the organic electroluminescent device according to the present invention in various electronic devices, and the electronic devices include, but are not limited to: display devices or lighting devices.

[0150] The following further elaborates on the organic electroluminescent materials, organic light-emitting devices, and their applications of the present invention in conjunction with specific examples and comparative examples. Examples of the synthesis methods of the host material and the guest material in the organic electroluminescent materials according to the present invention are given below, but the present invention is not limited to the following examples.

[0151] Synthesis of compound M1:

[0152]

[0153] The specific synthesis steps are as follows:

[0154] 1) Synthesis of intermediate M1-3: Under nitrogen atmosphere, (32.1 g, 100 mmol) of compound M1-1, (14.9 g, 100 mmol) of compound M1-2, (0.92 g, 1 mmol) of compound Pd 2 (dba) 3 , (0.4 g, 2 mmol) of the compound tri-tert-butylphosphine, (13.7 g, 150 mmol) of the compound sodium tert-butoxide and 200 mL of anhydrous toluene solvent were added into a 500 mL two-necked bottle, heated at 60°C, stirred for reaction for 6 hours, cooled to room temperature, quenched with water, and most of the solvent was removed by rotary evaporation of the reaction solution. The solution was dissolved in dichloromethane and washed with water three times. The organic liquid was collected and mixed with silica gel and purified by column to obtain intermediate M1-3. The eluent was petroleum ether: dichloromethane in a volume ratio of 3:1, with a yield of 80%.

[0155] 2) Synthesis of intermediate M1-6: Under nitrogen environment, (39.6 g, 100 mmol) of compound M1-4, (17.8 g, 100 mmol) of compound M1-5, (3.31 g, 3 mmol) of tetrakistriphenylphosphine palladium, (27.6 g, 200 mmol) of potassium carbonate in 50 mL of aqueous solution and 200 mL of toluene were added to a 500 mL three-necked flask, heated and stirred to 110 ° C for 12 hours, the reaction was terminated, cooled to room temperature, the filtrate was filtered, most of the solvent was evaporated by rotary evaporation, dissolved in dichloromethane and washed three times, the organic liquid was collected and mixed with silica gel column for purification to obtain intermediate M1-6, the eluent was petroleum ether: dichloromethane in a volume ratio of 5:1, and the yield was 70%.

[0156] 3) Synthesis of intermediate M1-7: Under nitrogen atmosphere, (24.2 g, 60 mmol) of compound M1-6, (23.4 g, 60 mmol) of compound M1-3, (0.55 g, 0.6 mmol) of compound Pd 2 (dba) 3, (0.24 g, 1.2 mmol) of the compound tri-tert-butylphosphine, (8.2 g, 90 mmol) of the compound sodium tert-butoxide and 150 mL of anhydrous toluene solvent were added into a 300 mL two-necked bottle, heated at 60°C, stirred for reaction for 6 hours, cooled to room temperature, quenched with water, and the reaction solution was rotary evaporated to remove most of the solvent, dissolved in dichloromethane and washed with water 3 times, the organic liquid was collected and mixed with silica gel and purified by column to obtain intermediate M1-7, the eluent was petroleum ether: dichloromethane in a volume ratio of 4:1, and the yield was 70%.

[0157] 4) Synthesis of intermediate M1-9: Under nitrogen environment, (28.5 g, 40 mmol) of compound M1-7, (11.3 g, 40 mmol) of compound M1-8, (0.37 g, 0.4 mmol) of compound Pd2(dba)3, (0.16 g, 0.8 mmol) of compound tri-tert-butylphosphine, (5.5 g, 60 mmol) of compound sodium tert-butoxide and 100 mL of anhydrous toluene solvent were added to a 250 mL two-necked flask, heated to 60 ° C, stirred for 6 hours, cooled to room temperature, quenched with water, and the reaction solution was rotary evaporated to remove most of the solvent, dissolved in dichloromethane and washed 3 times, the organic liquid was collected and mixed with silica gel column for purification to obtain intermediate M1-9, the eluent was petroleum ether: dichloromethane in a volume ratio of 2.5:1, and the yield was 70%.

[0158] 5) Synthesis of Compound M1: Under nitrogen environment, (18.3 g, 20 mmol) Compound M1-9 and 100 mL of anhydrous toluene solvent were added to a 300 mL three-necked flask, stirred to dissolve, cooled to -78°C, slowly added 45 mmol of tert-butyl lithium, reacted for 2 hours, added 50 mmol of boron tribromide at one time, allowed the reaction solution to slowly rise to room temperature, continued to stir and react for 3 hours, added 80 mmol of diisopropylethylamine at one time, heated to 100°C and reacted for 4 hours, after the reaction was completed, the reaction solution was rotary evaporated to remove most of the solvent, washed 3 times with dichloromethane, collected the organic solution, mixed with silica gel and purified by column to obtain Compound M1, the eluent was petroleum ether: dichloromethane in a volume ratio of 3.5:1, and the yield was 53%. MS (ASAP): 894.

[0159] Synthesis of compound M2:

[0160]

[0161] (1) Synthesis of intermediate M2-2: According to the synthesis method of compound M1-3, compound M2-1 was used instead of compound M1-1, with a yield of 85%.

[0162] (2) Synthesis of intermediate M2-3: According to the synthesis method of compound M1-7, compound M2-2 was used instead of compound M1-3, with a yield of 72%.

[0163] (3) Synthesis of intermediate M2-4: According to the synthesis method of compound M1-9, replace compound M1-7 with compound M2-3, with a yield of 68%.

[0164] (4) Synthesis of compound M2: According to the synthesis method of compound M1, replace compound M1-9 with compound M2-4, with a yield of 55%. MS(ASAP): 779.

[0165] Synthesis of compound M3:

[0166]

[0167] (1) Synthesis of intermediate M3-3: According to the synthesis method of compound M1-3, replace compound M1-1 and M1-2 with compounds M3-1 and M3-2 respectively, with a yield of 82%.

[0168] (2) Synthesis of intermediate M3-6: According to the synthesis method of compound M1-6, replace compound M1-4 and M1-5 with compounds M3-5 and M3-4 respectively, with a yield of 75%.

[0169] (3) Synthesis of intermediate M3-7: According to the synthesis method of compound M1-6, replace compound M1-5 with compound M3-4, with a yield of 68%.

[0170] (4) Synthesis of intermediate M3-8: According to the synthesis method of compound M1-7, replace compound M1-6 and M1-3 with compounds M3-7 and M3-3 respectively, with a yield of 72%.

[0171] (5) Synthesis of intermediate M3-9: According to the synthesis method of compound M1-9, replace compound M1-7 and M1-8 with compounds M3-8 and M3-6 respectively, with a yield of 73%.

[0172] (6) Synthesis of compound M3: According to the synthesis method of compound M1, replace compound M1-9 with compound M3-9, with a yield of 54%. MS(ASAP): 839.

[0173] Synthesis of compound M4:

[0174]

[0175] (1) Synthesis of intermediate M4-2: According to the synthesis method of compound M1-3, replace compound M1-1 and M1-2 with compounds M4-1 and M3-2 respectively, with a yield of 78%.

[0176] (2) Synthesis of intermediate M4-4: According to the synthesis method of compound M1-7, using compounds M4-3 and M4-2 to replace compounds M1-6 and M1-3 respectively, with a yield of 73%.

[0177] (3) Synthesis of intermediate M4-5: According to the synthesis method of compound M1-9, using compounds M4-4 and M3-6 to replace compounds M1-7 and M1-8 respectively, with a yield of 71%.

[0178] (4) Synthesis of compound M4: According to the synthesis method of compound M1, using compound M3-9 to replace compound M1-9, with a yield of 52%. MS(ASAP): 763.

[0179] Synthesis of compound M5:

[0180]

[0181] (1) Synthesis of intermediate M5-3: According to the synthesis method of compound M1-3, using compound M5-1 to replace compound M1-1, with a yield of 86%.

[0182] (2) Synthesis of intermediate M5-5: According to the synthesis method of compound M1-6, using compounds M5-4 and M5-3 to replace compounds M1-4 and M1-5 respectively, with a yield of 75%.

[0183] (3) Synthesis of intermediate M5-6: According to the synthesis method of compound M1-7, using compound M5-2 to replace compound M1-3, with a yield of 70%.

[0184] (4) Synthesis of intermediate M5-7: According to the synthesis method of compound M1-9, using compounds M5-6 and M5-5 to replace compounds M1-7 and M1-8 respectively, with a yield of 70%.

[0185] (5) Synthesis of compound M5: According to the synthesis method of compound M1, using compound M5-7 to replace compound M1-9, with a yield of 50%. MS(ASAP): 894.

[0186] Synthesis of compound M6:

[0187]

[0188] (1) Synthesis of intermediate M6-2: According to the synthesis method of compound M1-3, using compound M6-1 to replace compound M1-1, with a yield of 85%.

[0189] (2) Synthesis of intermediate M6-4: According to the synthesis method of compound M1-6, using compounds M3-5 and M6-3 to replace compounds M1-4 and M1-5 respectively, with a yield of 77%.

[0190] (3) Synthesis of intermediate M6-5: According to the synthesis method of compound M1-7, using compounds M3-7 and M6-2 to replace compounds M1-6 and M1-3 respectively, with a yield of 73%.

[0191] (4) Synthesis of intermediate M6-6: According to the synthesis method of compound M1-9, using compounds M6-5 and M6-4 to replace compounds M1-7 and M1-8 respectively, with a yield of 71%.

[0192] (5) Synthesis of compound M6: According to the synthesis method of compound M1, using compound M6-6 to replace compound M1-9, with a yield of 53%. MS(ASAP): 723.

[0193] Synthesis of compound M7:

[0194]

[0195] (1) Synthesis of intermediate M7-2: Under a nitrogen atmosphere, add (19.4 g, 100 mmol) of compound M7-1, (3.6 g, 150 mmol) of sodium hydride, and 200 mL of tetrahydrofuran solvent to a 500 mL two-necked flask, stir and react for 1 h, add (40.3 g, 100 mmol) of compound M1-6, continue to stir and react for 6 h, quench with water, rotary evaporate most of the solvent from the reaction solution, dissolve with dichloromethane, wash with water 3 times, collect the organic solution, mix with silica gel and purify by column chromatography to obtain intermediate M7-2. The eluent is petroleum ether:dichloromethane = 4:1 by volume, with a yield of 70%.

[0196] (2) Synthesis of intermediate M7-3: According to the synthesis method of compound M1-9, using compound M7-2 to replace compound M1-7, with a yield of 72%.

[0197] (3) Synthesis of compound M7: According to the synthesis method of compound M1, using compound M7-3 to replace compound M1-9, with a yield of 54%. MS(ASAP): 698.

[0198] Synthesis of compound M8:

[0199]

[0200] The specific synthesis steps are as follows:

[0201] 1) Synthesis of Intermediate M8-2: Under a nitrogen atmosphere, (28.8 g, 100 mmol) of Compound M8-1 and 150 mL of anhydrous tetrahydrofuran solvent were added to a 500 mL two-necked flask, stirred and dissolved, cooled to -78 °C, 100 mmol of n-butyllithium was slowly added dropwise while maintaining the temperature, and stirring was continued for 2 hours. 100 mmol of sulfur powder was added all at once, and the reaction was allowed to warm up to room temperature naturally. Stirring was continued for 4 hours. 100 mL of 2 mmol / mL ammonium chloride aqueous solution was added, and stirring was continued for 0.5 hour. Most of the solvent was removed by rotary evaporation of the reaction solution, dissolved in dichloromethane, washed three times with water, and the organic layer was collected and purified by silica gel column chromatography to obtain Intermediate M8-2. The eluent was petroleum ether:dichloromethane = 3:1 (v / v), and the yield was 70%.

[0202] 2) Synthesis of Intermediate M8-3: Referring to the synthesis method of Compound M7-2, Compound M8-2 was used instead of Compound M7-1, and the yield was 68%.

[0203] 3) Synthesis of Intermediate M8-5: Referring to the synthesis method of Compound M1-9, Compound M8-3 and Compound M8-4 were used instead of Compound M1-7 and Compound M1-8, and the yield was 70%.

[0204] 4) Synthesis of Compound M8: Referring to the synthesis method of Compound M1, Compound M8-5 was used instead of Compound M1-9, and the yield was 52%. MS(ASAP): 703.

[0205] Synthesis of Compound M9:

[0206]

[0207] (1) Synthesis of Intermediate M9-2: According to the synthesis method of Compound M1-3, Compound M9-1 was used instead of Compound M1-1, and the yield was 78%.

[0208] (2) Synthesis of Intermediate M9-3: According to the synthesis method of Compound M1-7, Compound M9-2 was used instead of Compound M1-3, and the yield was 69%.

[0209] (3) Synthesis of Intermediate M9-4: According to the synthesis method of Compound M1-9, Compound M9-3 was used instead of Compound M1-7, and the yield was 65%.

[0210] (4) Synthesis of Compound M9: According to the synthesis method of Compound M1, Compound M9-4 was used instead of Compound M1-9, and the yield was 50%. MS(ASAP): 841.

[0211] Synthesis of Compound M10:

[0212]

[0213] (1) Synthesis of intermediate M10-3: According to the synthesis method of compound M1-3, using compounds M10-1 and M10-2 to replace compounds M1-1 and M1-2, with a yield of 75%.

[0214] (2) Synthesis of intermediate M10-5: According to the synthesis method of compound M1-6, using compounds M5-4 and M10-4 to replace compounds M1-4 and M1-5 respectively, with a yield of 70%.

[0215] (3) Synthesis of intermediate M10-6: According to the synthesis method of compound M1-7, using compound M10-3 to replace compound M1-3, with a yield of 70%.

[0216] (4) Synthesis of intermediate M10-7: According to the synthesis method of compound M1-9, using compounds M10-6 and M10-5 to replace compounds M1-7 and M1-8, with a yield of 67%.

[0217] (5) Synthesis of compound M10: According to the synthesis method of compound M1, using compound M10-7 to replace compound M1-9, with a yield of 54%. MS(ASAP): 747.

[0218] Synthesis of compound M11:

[0219]

[0220] (1) Synthesis of intermediate M11-3: Under a nitrogen atmosphere, add (48.8 g, 100 mmol) of compound M11-1, (24.4 g, 200 mmol) of compound M11-2, (3.31 g, 3 mmol) of tetrakis(triphenylphosphine)palladium, an aqueous solution (50 mL) of (27.6 g, 200 mmol) of potassium carbonate, and 200 mL of toluene to a 500 mL three-necked flask. Heat and stir at 80 °C for 12 h, then cool to room temperature. Filter the filtrate by suction filtration, rotary evaporate most of the solvent, dissolve it with dichloromethane and wash it with water 3 times. Collect the organic solution, mix it with silica gel and purify it by column chromatography to obtain intermediate M11-3. The eluent is petroleum ether:dichloromethane = 4.5:1 by volume, with a yield of 67%.

[0221] (2) Synthesis of intermediate M11-5: Under a nitrogen atmosphere, add (23.3 g, 60 mmol) of compound M11-3, (20.3 g, 120 mmol) of compound M11-4, (1.1 g, 1.2 mmol) of compound Pd 2 (dba) 3, (0.48 g, 2.4 mmol) of the compound tris(tert-butyl)phosphine, (13.7 g, 90 mmol) of the compound sodium tert-butoxide and 150 mL of anhydrous toluene solvent were added to a 300 mL two-necked flask, heated to 60 °C, stirred and reacted for 6 h, then cooled to room temperature and quenched with water. The reaction solution was rotary evaporated to remove most of the solvent, dissolved in dichloromethane and washed with water 3 times. The organic layer was collected, mixed with silica gel and purified by column chromatography to obtain the intermediate M11-5. The eluent was petroleum ether:dichloromethane = 1.5:1 (v / v), and the yield was 65%.

[0222] (3) Synthesis of compound M11: Under a nitrogen atmosphere, (11.3 g, 20 mmol) of compound M11-5 and 100 mL of anhydrous toluene solvent were added to a 300 mL three-necked flask, stirred and dissolved, cooled to -78 °C, and 65 mmol of tert-butyllithium was slowly added dropwise. The reaction was carried out for 2 h, 70 mmol of boron tribromide was added, and the reaction solution was slowly warmed to room temperature and stirred for an additional 3 h. 100 mmol of diisopropylethylamine was added, and the reaction was heated to 100 °C for 4 h. The reaction solution was rotary evaporated to remove most of the solvent, dissolved in dichloromethane and washed with water 3 times. The organic layer was collected, mixed with silica gel and purified by column chromatography to obtain compound M11. The eluent was petroleum ether:dichloromethane = 3:1 (v / v), and the yield was 45%. MS(ASAP): 588.

[0223] Synthesis of compound M12:

[0224]

[0225] (1) Synthesis of intermediate M12-2: According to the synthesis method of compound M1-6, compounds M5-4 and M12-1 were used to replace compounds M1-4 and M1-5 respectively, and the yield was 69%.

[0226] (2) Synthesis of intermediate M12-3: According to the synthesis method of compound M11-3, compound M1-5 was used to replace compound M11-2, and the yield was 70%.

[0227] (3) Synthesis of intermediate M12-4: According to the synthesis method of compound M11-5, compounds M12-3 and M12-2 were used to replace compounds M11-3 and M11-4 respectively, and the yield was 63%.

[0228] (4) Synthesis of compound M12: According to the synthesis method of compound M11, compound M12-4 was used to replace compound M11-5, and the yield was 42%. MS(ASAP): 913.

[0229] Synthesis of compound M13:

[0230]

[0231] (1) Synthesis of intermediate M13-2: According to the synthesis method of compound M1-6, replace compound M1-4 and M1-5 with compound M5-4 and M13-1 respectively, with a yield of 69%.

[0232] (2) Synthesis of intermediate M13-3: According to the synthesis method of compound M11-5, replace compound M11-3 and M11-4 with compound M12-3 and M13-2 respectively, with a yield of 60%.

[0233] (3) Synthesis of compound M13: According to the synthesis method of compound M11, replace compound M11-5 with compound M13-3, with a yield of 46%. MS(ASAP): 1025.

[0234] Synthesis of compound M14:

[0235]

[0236] (1) Synthesis of intermediate M14-2: According to the synthesis method of compound M1-6, replace compound M1-4 and M1-5 with compound M5-4 and M14-1 respectively, with a yield of 70%.

[0237] (2) Synthesis of intermediate M14-3: According to the synthesis method of compound M11-5, replace compound M11-3 and M11-4 with compound M12-3 and M14-2 respectively, with a yield of 62%.

[0238] (3) Synthesis of compound M14: According to the synthesis method of compound M11, replace compound M11-5 with compound M14-3, with a yield of 44%. MS(ASAP): 1103.

[0239] Synthesis of compound M15:

[0240]

[0241] (1) Synthesis of intermediate M15-2: According to the synthesis method of compound M1-6, replace compound M1-4 and M1-5 with compound M5-4 and M15-1 respectively, with a yield of 72%.

[0242] (2) Synthesis of intermediate M15-3: According to the synthesis method of compound M11-5, replace compound M11-3 and M11-4 with compound M12-3 and M15-2 respectively, with a yield of 61%.

[0243] (3) Synthesis of compound M15: According to the synthesis method of compound M11, replace compound M11-5 with compound M15-3, with a yield of 47%. MS(ASAP): 893.

[0244] Synthesis of Compound M16:

[0245]

[0246] (1) Synthesis of Intermediate M16-1: According to the synthesis method of Compound M11-3, using Compound M12-1 to replace Compound M11-2, with a yield of 68%.

[0247] (2) Synthesis of Intermediate M16-2: According to the synthesis method of Compound M11-5, using Compounds M16-1 and M1-8 to replace Compounds M11-3 and M11-4 respectively, with a yield of 64%.

[0248] (3) Synthesis of Compound M16: According to the synthesis method of Compound M11, using Compound M16-2 to replace Compound M11-5, with a yield of 46%. MS(ASAP): 913.

[0249] Synthesis of Compound M17:

[0250]

[0251] (1) Synthesis of Intermediate M17-2: According to the synthesis method of Compound M11-3, using Compound M17-1 to replace Compound M11-2, with a yield of 69%.

[0252] (2) Synthesis of Intermediate M17-3: According to the synthesis method of Compound M11-5, using Compounds M17-2 and M1-8 to replace Compounds M11-3 and M11-4 respectively, with a yield of 66%.

[0253] (3) Synthesis of Compound M17: According to the synthesis method of Compound M11, using Compound M17-3 to replace Compound M11-5, with a yield of 41%. MS(ASAP): 1075.

[0254] Synthesis of Compound M18:

[0255]

[0256] (1) Synthesis of Intermediate M18-2: According to the synthesis method of Compound M11-3, using Compound M18-1 to replace Compound M11-2, with a yield of 67%.

[0257] (2) Synthesis of Intermediate M18-3: According to the synthesis method of Compound M11-5, using Compounds M18-2 and M1-8 to replace Compounds M11-3 and M11-4 respectively, with a yield of 64%.

[0258] (3) Synthesis of Compound M18: According to the synthesis method of Compound M11, replace Compound M11-5 with Compound M18-3, with a yield of 40%. MS(ASAP): 925.

[0259] Synthesis of Compound M19:

[0260]

[0261] (1) Synthesis of Intermediate M19-1: According to the synthesis method of Compound M1-6, replace Compound M1-4 with Compound M11-1, with a yield of 63%.

[0262] (2) Synthesis of Intermediate M19-2: According to the synthesis method of Compound M1-6, replace Compound M1-4 and M1-5 with Compound M19-1 and M6-3 respectively, with a yield of 68%.

[0263] (3) Synthesis of Intermediate M19-3: According to the synthesis method of Compound M11-5, replace Compound M11-3 and M11-4 with Compound M19-2 and M1-8 respectively, with a yield of 65%.

[0264] (4) Synthesis of Compound M19: According to the synthesis method of Compound M11, replace Compound M11-5 with Compound M19-3, with a yield of 44%. MS(ASAP): 917.

[0265] Synthesis of Compound M20:

[0266]

[0267] (1) Synthesis of Intermediate M20-1: According to the synthesis method of Compound M1-6, replace Compound M1-4 and M1-5 with Compound M5-4 and M18-1 respectively, with a yield of 73%.

[0268] (2) Synthesis of Intermediate M20-2: According to the synthesis method of Compound M1-7, replace Compound M1-6 and M1-3 with Compound M12-3 and M1-8 respectively, with a yield of 64%.

[0269] (3) Synthesis of Intermediate M20-3: According to the synthesis method of Compound M1-7, replace Compound M1-6 and M1-3 with Compound M20-2 and M20-1 respectively, with a yield of 68%.

[0270] (4) Synthesis of Compound M20: According to the synthesis method of Compound M11, replace Compound M11-5 with Compound M20-3, with a yield of 42%. MS(ASAP): 869.

[0271] Synthesis of Compound M21:

[0272]

[0273] (1) Synthesis of intermediate M21-3: According to the synthesis method of compound M1-6, replace compounds M1-5 and M1-4 with compounds M21-1 and M21-2 respectively, with a yield of 75%.

[0274] (2) Synthesis of intermediate M21-5: Under a nitrogen atmosphere, add (29.8 g, 60 mmol) of compound M21-3, phenol (11.3 g, 120 mmol), potassium carbonate (27.6 g, 200 mmol), and 200 mL of N,N-dimethylformamide solvent to a 500 mL three-necked flask. Stir and react at 155 °C for 12 h, cool to room temperature, pour the reaction solution into 300 mL of pure water, extract with dichloromethane and wash three times with water. Collect the organic solution, mix with silica gel and purify by column chromatography. The eluent is petroleum ether:dichloromethane = 4:1 by volume, with a yield of 65%.

[0275] (3) Synthesis of compound M21: Under a nitrogen atmosphere, add (12.9 g, 20 mmol) of compound M21-5 and 100 mL of anhydrous toluene solvent to a 300 mL three-necked flask, stir to dissolve, cool to -78 °C, slowly add 25 mmol of n-butyllithium dropwise, react for 2 h, add 30 mmol of boron tribromide all at once, let the reaction solution slowly rise to room temperature, continue to stir and react for 3 h, add 40 mmol of diisopropylethylamine all at once, and heat and react at 100 °C for 4 h. Rotate and evaporate most of the solvent from the reaction solution, dissolve with dichloromethane and wash three times with water. Collect the organic solution, mix with silica gel and purify by column chromatography. The eluent is petroleum ether:dichloromethane = 3:1 by volume, with a yield of 56%. MS (ASAP): 575.

[0276] Synthesis of compound M22:

[0277]

[0278] (1) Synthesis of intermediate M22-2: According to the synthesis method of compound M1-6, replace compounds M1-5 and M1-4 with compounds M22-1 and M21-2 respectively, with a yield of 73%.

[0279] (2) Synthesis of intermediate M22-3: According to the synthesis method of compound M21-5, replace compound M21-3 with compound M22-2, with a yield of 67%.

[0280] (3) Synthesis of compound M22: According to the synthesis method of compound M21, replace compound M21-5 with compound M22-3, with a yield of 55%. MS (ASAP): 599.

[0281] Synthesis of compound M23:

[0282]

[0283] (1) Synthesis of intermediate M23-2: According to the synthesis method of compound M1-6, replace compound M1-5 and M1-4 with compound M23-1 and M21-2 respectively, with a yield of 70%.

[0284] (2) Synthesis of intermediate M23-3: According to the synthesis method of compound M21-5, replace compound M21-3 with compound M23-2, with a yield of 69%.

[0285] (3) Synthesis of compound M23: According to the synthesis method of compound M21, replace compound M21-5 with compound M23-3, with a yield of 53%. MS(ASAP): 588.

[0286] Synthesis of compound M24:

[0287]

[0288] (1) Synthesis of intermediate M24-2: Under a nitrogen atmosphere, add compound M24-1 (19.3 g, 100 mmol), phenol (94.1 g, 100 mmol), potassium carbonate (20.7 g, 150 mmol), and 200 mL of N,N-dimethylformamide solvent to a 500 mL three-necked flask, stir and react at 155 °C for 12 h, cool to room temperature, pour the reaction solution into 300 mL of pure water, extract with dichloromethane and wash three times with water, collect the organic solution, mix with silica gel and purify by column chromatography, and the eluent is petroleum ether:dichloromethane = 5:1 by volume, with a yield of 75%.

[0289] (2) Synthesis of intermediate M24-5: According to the synthesis method of compound M1-6, replace compound M1-5 and M1-4 with compound M24-3 and M24-4 respectively, with a yield of 86%.

[0290] (3) Synthesis of intermediate M24-6: Under a nitrogen atmosphere, add compound M24-5 (21 g, 60 mmol), 60 mL of hydrobromic acid and 100 mL of acetic acid solvent to a 300 mL three-necked flask, heat under reflux and react for 12 h, cool to room temperature, pour the reaction solution into 300 mL of pure water, extract with dichloromethane and wash three times with water, collect the organic solution, mix with silica gel and purify by column chromatography, and the eluent is petroleum ether:dichloromethane = 3:1 by volume, with a yield of 85%.

[0291] (4) Synthesis of intermediate M24-7: According to the synthesis method of compound M24-2, replace compound M24-1 and M21-4 with compound M24-4 and M24-6 respectively, with a yield of 82%.

[0292] (5) Synthesis of Compound M24: According to the synthesis method of Compound M21, replace Compound M21-5 with Compound M24-7, with a yield of 57%. MS (ASAP): 512.

[0293] Synthesis of Compound M25:

[0294]

[0295] (1) Synthesis of Intermediate M25-2: According to the synthesis method of Compound M1-6, replace Compound M1-5 and M1-4 with Compound M12-1 and M21-2 respectively, with a yield of 71%.

[0296] (2) Synthesis of Intermediate M25-4: According to the synthesis method of Compound M21-5, replace Compound M21-3 and M21-4 with Compound M25-2 and M25-3 respectively, with a yield of 64%.

[0297] (3) Synthesis of Compound M25: According to the synthesis method of Compound M21, replace Compound M21-5 with Compound M25-4, with a yield of 52%. MS (ASAP): 549.

[0298] Synthesis of Compound M26:

[0299]

[0300] (1) Synthesis of Intermediate M26-2: According to the synthesis method of Compound M1-6, replace Compound M1-5 and M1-4 with Compound M26-1 and M26-2 respectively, with a yield of 67%.

[0301] (2) Synthesis of Intermediate M26-5: Under a nitrogen atmosphere, add (21.1 g, 60 mmol) of Compound M26-3, (12.8 g, 60 mmol) of Compound M26-4, (26.1 g, 80 mmol) of cesium carbonate, (0.2 g, 3 mmol) of copper powder and 200 mL of acetonitrile to a 500 mL three-necked flask, stir and react at 80 °C for 12 h, and cool to room temperature. Rotate and evaporate most of the solvent, pour the reaction solution into 150 mL of pure water, extract and wash with dichloromethane 3 times, collect the organic solution, mix with silica gel and purify by column chromatography, and the eluent is petroleum ether:dichloromethane = 3:1 by volume, with a yield of 52%.

[0302] (3) Synthesis of Intermediate M26-7: According to the synthesis method of Compound M24-2, replace Compound M24-1 and M21-4 with Compound M26-6 and M26-5 respectively, with a yield of 76%.

[0303] (4) Synthesis of Compound M26: According to the synthesis method of Compound M21, replace Compound M21-5 with Compound M26-7, with a yield of 56%. MS (ASAP): 568.

[0304] Synthesis of Compound M27:

[0305]

[0306] (1) Synthesis of Intermediate M27-3: According to the synthesis method of Compound M26-5, replace Compound M26-4 and Compound M26-3 with Compound M27-1 and Compound M27-2 respectively, with a yield of 56%.

[0307] (2) Synthesis of Intermediate M27-5: According to the synthesis method of Compound M26-5, replace Compound M26-3 and Compound M26-4 with Compound M27-3 and Compound M27-4 respectively, with a yield of 62%.

[0308] (3) Synthesis of Compound M27: According to the synthesis method of Compound M1, replace Compound M1-9 with Compound M27-5, with a yield of 52%. MS (ASAP): 537.

[0309] Synthesis of Compound M28:

[0310]

[0311] (1) Synthesis of Intermediate M28-3: According to the synthesis method of Compound M1-6, replace Compound M1-5 and Compound M1-4 with Compound M28-1 and Compound M28-2 respectively, with a yield of 70%.

[0312] (2) Synthesis of Intermediate M28-5: According to the synthesis method of Compound M26-5, replace Compound M26-3 and Compound M26-4 with Compound M28-3 and twice the amount of Compound M28-4 respectively, with a yield of 48%.

[0313] (3) Synthesis of Compound M28: According to the synthesis method of Compound M1, replace Compound M1-9 with Compound M28-5, with a yield of 56%. MS (ASAP): 645.

[0314] Synthesis of Compound M29:

[0315]

[0316] (1) Synthesis of Intermediate M29-3: According to the synthesis method of Compound M1-6, replace Compound M1-5 and Compound M1-4 with Compound M29-1 and Compound M29-2 respectively, with a yield of 67%.

[0317] (2) Synthesis of Intermediate M29-5: According to the synthesis method of Compound M26-5, replace Compounds M26-3 and M26-4 with Compounds M29-3 and M29-4 respectively, with a yield of 56%.

[0318] (3) Synthesis of Intermediate M29-7: According to the synthesis method of Compound M26-5, replace Compounds M26-3 and M26-4 with Compounds M29-5 and M29-6 respectively, with a yield of 62%.

[0319] (4) Synthesis of Compound M29: According to the synthesis method of Compound M1, replace Compound M1-9 with Compound M29-7, with a yield of 59%. MS(ASAP): 663.

[0320] Synthesis of Compound M30:

[0321]

[0322] (1) Synthesis of Intermediate M30-3: According to the synthesis method of Compound M1-6, replace Compounds M1-5 and M1-4 with Compounds M30-1 and M30-2 respectively, with a yield of 64%.

[0323] (2) Synthesis of Intermediate M30-6: According to the synthesis method of Compound M26-5, replace Compounds M26-3 and M26-4 with Compounds M30-3 and twice of M30-4 respectively, with a yield of 52%.

[0324] (3) Synthesis of Compound M30: According to the synthesis method of Compound M1, replace Compound M1-9 with Compound M30-6, with a yield of 56%. MS(ASAP): 724.

[0325] Fabrication of OLED Devices

[0326] The fabrication process of OLED devices is described in detail through specific examples below. The structure of the OLED device is:

[0327] ITO / HIL(40nm) / HTL(100nm) / EML(50nm) / ETL(25nm) / LiQ(1nm) / Al(150nm) / Cathode.

[0328] The structural formulas and preparation steps of the materials used for each layer are as follows:

[0329] Structural formulas of the materials used:

[0330] Materials used for the hole injection layer: Materials used for the hole transport layer: Materials used for the electron transport layer: The guest materials of the light-emitting layer are M1 to M20 and Ref-2 respectively: The host materials of the light-emitting layer are M21 to M30 and Ref-1 respectively: The structure of LiQ is:

[0331] Example 1

[0332] (1) After cleaning the conductive glass substrate with chloroform, acetone, and isopropyl alcohol in sequence, perform ultraviolet ozone plasma treatment on it;

[0333] (2) Hole injection layer (40 nm): Prepared into a film by solution processing method;

[0334] (3) Hole transport layer (100 nm): Prepared into a film by solution processing method;

[0335] (4) Light-emitting layer (50 nm): Select M1 as the guest material and M28 as the host material, and prepare it into a film by solution processing method; The weight ratio of the host material to the guest material is: 95:5;

[0336] (5) Electron transport layer (25 nm): Thermally evaporated in high vacuum (1×10 -6 mbar);

[0337] (6) Cathode: LiQ / Al (1 nm / 150 nm) thermally evaporated in high vacuum (1×10 -6 mbar);

[0338] (7) Encapsulation: The device is encapsulated with ultraviolet curable resin in a nitrogen glove box.

[0339] Examples 2 to 37, Comparative Examples 1 - 6

[0340] The preparation method is basically the same as that of Example 1, except that the host and guest materials of the light-emitting layer are different, as shown in the following table.

[0341] Use the characterization equipment to test the current-voltage (J-V) characteristics of the organic light-emitting diodes of Examples 1 to 37 and Comparative Examples 1 to 6 of the device, and record the external quantum efficiency and lifetime at the same time (see Table 1). In Table 1, all the external quantum efficiencies and lifetimes are relative values with respect to the organic light-emitting diode of Comparative Example 1.

[0342] Table 1 Host and guest materials of the light-emitting layer of the organic light-emitting diode, and luminous efficiency and lifetime

[0343]

[0344]

[0345] As can be seen from the above table, in the organic electroluminescent device (OLED) provided by the present invention, by selecting appropriate host and guest materials as the light-emitting layer materials, the luminous efficiency and lifespan of the OLED are significantly improved.

[0346] The technical features of the above-described embodiments can be combined arbitrarily. For the sake of brevity of description, 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, it should be considered as falling within the scope described in this specification.

[0347] The above-described embodiments merely represent several implementation manners of the present invention. The description thereof is relatively specific and detailed, but it should not be construed as a limitation on the scope of the invention patent. It should be noted that for those of ordinary skill in the art, without departing from the concept of the present invention, several modifications and improvements can still be made, and these all belong to the protection scope of the present invention. Therefore, the protection scope of the invention patent should be subject to the appended claims.

Claims

1. An organic electroluminescent 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 at least comprises a light-emitting layer, and the light-emitting layer material comprises a host material and a guest material. Characterized in that, the guest material has a structure represented by Formula (1) or Formula (2), and the host material has a structure represented by any one of General Formulas (7-1) to (7-8): wherein each occurrence of Z is independently selected from NR 2 , O or S, and R 2 is selected from -H, -D, a straight-chain alkyl group having 1 to 5 C atoms, a branched-chain alkyl group having 3 to 10 C atoms, or the following structure: R 10 Each occurrence is independently selected from -H, -D, methyl, isopropyl, tert-butyl or phenyl, n 3 is any integer selected from 1 to 4; Ar 1 ~Ar 7 Each independently selected from any one of the following groups: X 1 Each occurrence is independently selected from CR 5 , R 5 is selected from -H, -D, a straight-chain alkyl group having 1 to 8 C atoms or a branched-chain alkyl group having 3 to 8 C atoms; Y is independently selected from NR each time it appears 6 , CR 7 R 8 , O or S, R 6 is selected from isopropyl, tert-butyl or phenyl, R 7 and R 8 are selected from methyl; R 1 Each occurrence is independently selected from -H, -D, a straight-chain alkyl group having 1 to 8 C atoms, or a branched-chain alkyl group having 3 to 8 C atoms; R 5 selected from the following groups: Y 1 It has the same meaning as described by Y.

2. The organic electroluminescent device according to Claim 1, Characterized in that, the organic functional layer further comprises at least one layer selected from an electron injection layer, an electron transport layer, an electron blocking layer, a hole injection layer, a hole transport layer, and a hole blocking layer.

3. The organic electroluminescent device according to Claim 1, Characterized in that, the organic electroluminescent device is an organic light-emitting diode, an organic photovoltaic cell, an organic light-emitting battery, an organic field effect transistor, an organic light-emitting field effect transistor, an organic laser, an organic spintronic device, an organic sensor, or an organic plasmonic emitter diode.

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