Condensed polycyclic compound, an associated manufacturing process and an associated use

DE112018000255B4Active Publication Date: 2025-02-13NINGBO LUMILAN NEW MATERIAL CO LTD
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Patent Information

Application Number
DE112018000255
Authority / Receiving Office
DE · DE
Patent Type
Patents
Current Assignee / Owner
Priority Date
2018-06-28
Filing Date
2018-10-31
Publication Date
2025-02-13
Estimated Expiration
2038-10-31

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Abstract

A condensed cyclic compound with a structure of formula (II): where X1 is selected from N or CR 1a , X2 is selected from N or CR 2a , X3 is selected from N or CR 3a , X4 is selected from N or CR 4a , X5 is selected from N or CR 5a , X6 is selected from N or CR 6a , and X7 is selected from N or CR 7a , where R 1a - R 7a independently of each other from hydrogen, halogen, cyano group, substituted or unsubstituted alkyl group from C1 to C 30 , substituted or unsubstituted alkenyl group from C2 to C 30 , substituted or unsubstituted alkynyl group from C2 to C 30 , substituted or unsubstituted naphthenic group from C3 to C 30 , substituted or unsubstituted alkoxy group from C1 to C 30 , substituted or unsubstituted silane group from C1 to C30 , substituted or unsubstituted aryl group from C6 to C 60 or substituted or unsubstituted heteroaryl group from C3 to C 30 to be elected R1 and R2 are formed independently of each other from hydrogen, halogen, cyano group, substituted or unsubstituted alkyl group from C1 to C 30 , substituted or unsubstituted alkenyl group from C2 to C 30 , substituted or unsubstituted alkynyl group from C2 to C 30 , substituted or unsubstituted naphthenic group from C3 to C 30 , substituted or unsubstituted alkoxy group from C1 to C 30 , substituted or unsubstituted silane group from C1 to C 30 , substituted or unsubstituted aryl group from C6 to C 60 or substituted or unsubstituted heteroaryl group from C3 to C 30 to be elected Ar1 is selected from one of the following groups, and R1, R2, R1a , R 2a , R 3a , R 4a , R 5a , R6a and R7a are each independently selected from hydrogen or one of the following groups: wherein X is nitrogen, oxygen or sulfur, Y is independently either nitrogen or carbon; and in which at least one Y is nitrogen; and n is an integer from 0-5, m is an integer from 0-7, p is an integer from 0-6, q is an integer from 0-8, and t is an integer from 0-7; and a single or double bond; R3 is each independently selected from hydrogen; and Ar3ist jeweils unabhängig ausgewählt aus, Coronenyl, Pentalenyl, Indenyl, Naphthyl, Azulenyl, Fluorenyl, Heptalenyl, Octalenyl, Benz odiindenyl, Acenaphthylenyl, Phenalenyl, Phenanthrenyl, Anthracenyl, Triindenyl, Fluoranthen yl,Benzopyrenyl,Benzoperylenyl,Benzofluoranthenyl,Acephenanthrenyl,Aceanthrylenyl, 9,10-Benzophenanthrenyl,Pyrenyl, 1,2-Benzophenanthrenyl, ,Naphthacenyl,Pleiadenyl,Picenyl,Perylenyl, ,Pentacenyl, ,Cholanthrenyl,Helicenyl, ,Rubicenyl, Coronenyl, Trinaphthylenyl, ‚Pyranthrenyl, Ovalenyl, Corannulenyl, Anthanthrenyl, Truxenyl, Pyranyl, Benzopyranyl, Furyl ,Benzofuryl, Isobenzofuryl, Oxanthracenyl, Oxazolinyl, Dibenzofuryl, Peri-Xanthenoxanthenyl, Thienyl, Thioxanthenyl, Thianthrenyl, Phenoxathiinyl, Thionaphthenyl, Is othionaphthenyl, Thiophanthrenyl, Dibenzothienyl, Benzothienyl, Pyrrolyl, Pyrazolyl, Telluraz olyl,Selenazolyl, Thiazolyl, Isothiazolyl, Oxazolyl, Oxadiazolyl, Furazanyl, Pyridinyl, Pyraziny 1, Pyrimidinyl, Pyridazinyl, Triazinyl, Indolizinyl, Indolyl,Isoindolyl, Indazolyl, Purinyl, Quinolizinyl, Isoquinolyl, Carbazolyl, Fluorenocarbazolyl, Indolocarbazolyl, Imidazolyl, Naphthyridinyl, Phthalazinyl, Quinazolinyl, Benzodiazepinyl, Quinoxalinyl, Cinnolinyl, Quinolyl, Pteridinyl, Phenanthridinyl,Acridinyl,Perimidinyl,Phenanthrolinyl,Phenazinyl,Carbolinyl,Phenotellura zinyl, Phenoselenazinyl, Phenothiazinyl, Phenoxazinyl, Triphenodithiazinyl, Azadibenzofuryl, Triphenodioxazinyl, Anthrazinyl, Benzothiazolyl, Benzoimidazolyl, Benzoxazolyl, benzisoxa zolyl or benzoisothiazolyl; and , L is a single bond, a substituted or unsubstituted aliphatic C1-C10 hydrocarbon group, a substituted or unsubstituted C6-C60 aryl group or a substituted or unsubstituted C3-C30 heteroaryl group, wherein the heteroaryl has at least one heteroatom that is independently selected from nitrogen, sulfur, oxygen, phosphorus, boron or silicon.
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Description

FIELD OF THE INVENTION

[0001] The present invention relates to the field of display technology, specifically a condensed polycyclic compound, an associated manufacturing process and an associated use. STATE OF THE ART

[0002] In 1965, Pope et al. first discovered the electroluminescent properties of monocrystalline anthracene, marking the first discovery of electroluminescence in organic compounds. In 1987, Tang et al. of the American company Kodak successfully developed a low-voltage, high-brightness organic light-emitting diode (OLED) using a small-molecule organic semiconductor material. As a novel display technology, the organic electroluminescent diode is advantageously characterized by its self-illuminating properties, wide viewing angle, low energy consumption, high color gamut, fast response time, wide applicable temperature range, and the possibility of creating flexible displays. It has promising application prospects and is gaining increasing importance.

[0003] OLEDs typically employ a sandwich structure, in which an organic light-emitting layer is sandwiched between electrodes on both sides. The light emission principle works as follows: Driven by an external electric field, electrons and holes are injected via a cathode and an anode, respectively, into an organic electron conduction layer and a hole conduction layer. They then recombine within an organic light-emitting layer, forming an exciton that returns to its ground state through a radiative transition and emits light. During electroluminescence, singlet and triplet excitons are generated simultaneously. Based on the electron spin statistics law, the ratio of singlet to triplet excitons is estimated to be 1:3. Through a transition, the singlet excitons return to their ground state, and the material emits fluorescent light.

[0004] As the organic electroluminescent material with the longest history of application, fluorescent materials are available in numerous forms and at affordable prices. However, due to the limitations of electron spin blocking, only 25% of the singlet excitons can be used for light emission. This low internal quantum efficiency limits the device's efficiency. In a fluorescent material, energy from singlet excitons is transferred to triplet excitons via spin coupling of heavy atoms, which then emit fluorescent light. Theoretically, an internal quantum efficiency of 100% can be achieved. However, in fluorescent devices, concentration fluorescence quenching and triplet-triplet annihilation typically occur, which impairs the devices' light emission efficiency.

[0005] Doped OLED devices offer advantages in terms of light emission efficiency, which is why a light-emitting layer is typically formed by doping a host material with a guest material. The host material is a crucial factor influencing the light emission efficiency and performance of an OLED device. 4,4'-Bis(9H-carbazol-9-yl)biphenyl (CBP) is a widely used host material with good hole conduction properties. However, when CBP is used as the host material, the molecular packing and film morphology are easily altered during operation due to its low glass transition temperature, and the molecules are prone to recrystallization. This can reduce the operational performance and light emission efficiency of the OLED device.On the other hand, CBP is a hole-based host material in which, in addition to low exciton recombination efficiency, suboptimal properties of the light-emitting region, and severe roll-oft behavior during operation, electron and hole conduction is unbalanced. Furthermore, the triplet energy of CBP is lower than that of a blue light-emitting doped material, resulting in low energy transfer efficiency from the host material to the guest material and reduced device efficiency.

[0006] Furthermore, publication CN107108623A reveals a heterocyclic compound with the tall and upright structure of dibenzazepine. REVELATION OF THE INVENTION

[0007] Therefore, the present invention is based on the objective of overcoming the disadvantages in the prior art in that the host material of the light-emitting layer has a low triplet energy level and is easy to crystallize, whereby, in addition to unbalanced charge transfer of the host material and non-ideal properties of the light-emitting area, the energy of the host material cannot be efficiently transferred to the guest material, which leads to a low light emission efficiency and power of the device.

[0008] According to the invention, the problem is solved by the subject matter of the independent claim. Advantageous embodiments are the subject matter of the dependent claims. From a first point of view, the present invention provides a condensed polycyclic compound having the structure according to formula (1) or formula (II): where X1 is from N or CR 1a , X2 from N or CR 2a, X3 from N or CR 3a , X4 from N or CR 4a , X5 from N or CR 5a , X6 from N or CR 6a and X7 from N or CR 7a is chosen where R 1a to R 7a can be selected independently of each other from hydrogen, halogen, cyano group, alkyl group, alkenyl group, alkynyl group, naphthenic group, alkoxy group, silane group, aryl group or heteroaryl group, wherein R1 and R2 are chosen independently of each other from hydrogen, halogen, cyano group, alkyl group, alkenyl group, alkynyl group, naphthenic group, alkoxy group, silane group, aryl group or heteroaryl group, where L represents a single bond, a substituted bond, or an unsubstituted bond. aliphatic group from C1 to C 10 , a substituted or unsubstituted aryl group from C6 to C60 or a substituted or unsubstituted heteroaryl group from C3 to C30, where Ar1 is chosen from hydrogen, halogen, cyano group, alkyl group, alkenyl group, alkynyl group, naphthenic group, alkoxy group, silane group, aryl group or heteroaryl group, and wherein the heteroaryl group comprises at least one heteroatom, independently chosen from nitrogen, sulfur, oxygen, phosphorus, boron or silicon.

[0009] Preferably, the condensed polycyclic compound is provided that R1 and R2 are formed independently of each other from hydrogen, halogen, cyano group, substituted or unsubstituted alkyl group from C1 to C 30 , substituted or unsubstituted alkenyl group from C2 to C 30 , substituted or unsubstituted alkynyl group from C2 to C 30 , substituted or unsubstituted naphthenic group from C3 to C 30 , substituted or unsubstituted alkoxy group from C1 to C 30, substituted or unsubstituted silane group from C1 to C 30 , substituted or unsubstituted aryl group from C6 to C 60 or substituted or unsubstituted heteroaryl group from C3 to C 30 to be elected Ar1 consisting of hydrogen, halogen, cyano group, substituted or unsubstituted alkyl group from C1 to C 30 , substituted or unsubstituted alkenyl group from C2 to C 30 , substituted or unsubstituted alkynyl group from C2 to C 30 , substituted or unsubstituted naphthenic group from C3 to C 30 , substituted or unsubstituted alkoxy group from C1 to C 30 , substituted or unsubstituted silane group from C1 to C 30 , substituted or unsubstituted aryl group from C6 to C 60 or substituted or unsubstituted heteroaryl group from C3 to C 30 to be elected and that R 1a and R7a independently of each other from hydrogen, halogen, cyano group, substituted or unsubstituted alkyl group from C1 to C 30 , substituted or unsubstituted alkenyl group from C2 to C 30 , substituted or unsubstituted alkynyl group from C2 to C 30 , substituted or unsubstituted naphthenic group from C3 to C 30 , substituted or unsubstituted alkoxy group from C1 to C 30 , substituted or unsubstituted silane group from C1 to C 30 , substituted or unsubstituted aryl group from C6 to C 60 or substituted or unsubstituted heteroaryl group from C3 to C 30 to be elected Preferably, in the condensed polycyclic compound, Ar1 is provided from any of the following groups and R1, R2, R 1a , R 2a , R 3a , R 4a , R 5a , R 6a as well as R 7aare chosen independently of each other from hydrogen or any of the following groups: where X is nitrogen, oxygen or sulfur and Y is dependent on each other, either nitrogen or oxygen, and at least one of Y is nitrogen. where n is an integer from 0 to 5, m is an integer from 0 to 7, p is an integer from 0 to 6, q is an integer from 0 to 8, t is an integer from 0 to 7, and whether it is a single bond or a double bond where R3 is chosen independently from a substituted or unsubstituted alkyl group or from a substituted or unsubstituted hydrogen group, and wherein Ar3 is independently composed of hydrogen, alkyl group, coronene group, pentalene group, indene group, naphthalene group, azulene group, fluorene group, heptalene group, octalene group, benzindene group, acenaphthylene group, phenalene group, phenanthryl group, anthryl group, triindenyl group, fluoranthene group, benzopyrene group, benzoperylene group, benzofluoroanthrene group, acephenanthryl group, aceanthrylene group, 9,10-benzophenanthrene group, pyrene group, 1,2-benzophenanthrene group, butylbenzene group, tetracene group, pleiadene group, pyrene group, perylene group, pentaphene group, pentacene group, quaternary tetraphenyl group, cholanthrene group, helicene group, hexaphene group, rubicene group, coronene group, trinaphthylene group, heptaphene group, pyranthrene group, ovalene group, Corannulene group, anthanthrene group, truxene group, pyran group, benzopyran group, furan group, benzofuran group, isobenzofuran group, xanthene group, oxazoline group, dibenzofuran group, peri-xanthenoxanthene group,Thiophene group, thiaxanthene group, thianthrene group, phenoxathiine group, thianaphthen group, isothianaphthen group, thiophanthrene group, dibenzothiophene group, benzothiophene group, pyrrole group, pyrazole group, tellurazole group, selenazole group, thiazole group, isothiazole group, oxazole group, oxadiazole group, furazan group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, triazine group, indole group, indole group, isofindole group, indazole group, purine group, quinolizine group, isoquinoline group, carbazole group, fluorenocarbazole group, indolocarbazole group, imidazole group, naphthyridine group, phthalazine group, quinazoline group, benzodiazepine group, quinoxaline group, cinnoline group, quinoline group, pteridine group, phenanthridine group Acridine group, perimidine group, phenanthroline group, phenazine group, carboline group, phenotellurazine group, phenoselenazine group, phenothiazine group, phenoxazine group, triphenodithiazine group, aza-dibenzofuran group, triphenodioxazine groupThe anthrazine group, benzothiazole group, benzimidazole group, benzoxazole group, benzisoxazole group or benzisothiazole group is selected.

[0010] Preferably, the condensed polycyclic compound has the following molecular structure:

[0011] From a second perspective, the present invention provides a method for producing the condensed polycyclic compound.

[0012] The compound according to formula (I) is synthesized using the following steps: - Using the compound according to formula (A) and the compound according to formula (B) as starting materials, obtaining an intermediate 1 by a coupling reaction under the influence of a catalyst, obtaining an intermediate 2 after cyclization of intermediate 1 and obtaining the compound according to formula (I) by a substitution reaction or a coupling reaction of intermediate 2 with compound T3-L-Ar1 under the influence of a catalyst, the compound according to formula (I) is synthesized using the following synthesis route:

[0013] The compound is synthesized according to formula (II) using the following steps: - Using the compound according to formula (C) and the compound according to formula (E) as starting materials, obtaining an intermediate 3 by a coupling reaction under the influence of a catalyst, obtaining an intermediate 4 after cyclization of intermediate 3, obtaining an intermediate 5 by a coupling reaction after reduction of a nitro group of intermediate 4 and obtaining the compound according to formula (II) by a substitution reaction or a coupling reaction of intermediate 5 with compound T3-L-Ar1 under the influence of a catalyst, wherein the compound according to formula (II) is synthesized by the following synthesis route: and wherein T1 to T6 are chosen independently of each other from hydrogen, fluorine, chlorine, bromine or iodine.

[0014] From a third perspective, the present invention provides a method for producing the condensed polycyclic compound.

[0015] The compound according to formula (I) is synthesized using the following steps: - Using the compound according to formula (A') and the compound according to formula (B') as starting materials, obtaining an intermediate 1' by a coupling reaction under the influence of a catalyst, obtaining an intermediate 2' after cyclization of intermediate 1' and obtaining the compound according to formula (I) by a substitution reaction or a coupling reaction of intermediate 2' with compound T3-L-Ar1 under the influence of a catalyst, the compound according to formula (I) is synthesized using the following synthesis route:

[0016] The compound is synthesized according to formula (II) using the following steps: - Using the compound according to formula (C') and the compound according to formula (E') as starting materials, obtaining an intermediate 3' by a coupling reaction under the influence of a catalyst, obtaining an intermediate 4' after cyclization of intermediate 3', obtaining an intermediate 5' by a coupling reaction after reduction of a nitro group of intermediate 4' and obtaining the compound according to formula (II) by a substitution reaction or a coupling reaction of intermediate 5' with compound T3-L-Ar1 under the influence of a catalyst, wherein the compound according to formula (II) is synthesized by the following synthesis route: and wherein T1 to T5 are chosen independently of each other from hydrogen, fluorine, chlorine, bromine or iodine.

[0017] According to a fourth point, the present invention provides for the use of the condensed polycyclic compound as an organic electroluminescent material.

[0018] According to a fifth aspect, the present invention provides an organic electroluminescence device, wherein the condensed polycyclic compound is contained in at least one functional layer of the organic electroluminescence device.

[0019] Preferably, in the organic electroluminescence device, the functional layer is a light-emitting layer.

[0020] Furthermore, it is preferably provided in the organic electroluminescence device that the material of the light-emitting layer comprises a host material and a light-emitting guest dye, wherein the host material is the condensed polycyclic compound.

[0021] The embodiment according to the invention is characterized by the following advantages: 1. The condensed polycyclic compound according to the invention has the structure according to formula (I) or formula (II). In the condensed polycyclic compound, the effective conjugation in the parent core structure is increased by appropriately shaping the condensation of an aromatic ring and a heterocycle in the parent core structure. This not only improves the hole properties of the condensed polycyclic compound but also helps to balance the electron conduction behavior of the molecules of the material. By controlling the conjugation of the molecules, the HOMO energy level of the condensed polycyclic compound is increased, and the difference between the singlet and triplet energy levels of the molecules of the material is reduced.If this is used as the host material of a light-emitting layer, a better matching of the HOMO energy level of the light-emitting layer to the hole injection layer can be achieved, which contributes to the injection of the holes.

[0022] By incorporating X1 to X7, the condensed polycyclic compound can exhibit both electron conduction and hole conduction properties. When used as the host material of a light-emitting layer, the electron-to-hole ratio in the layer can be balanced, the recombination probability of charge carriers increased, and the recombination range for charge carriers expanded, resulting in improved light emission efficiency.

[0023] On the other hand, the condensed polycyclic compound of formula (I) or formula (II) exhibits a high energy level in the triplet (T1) and a high glass transition temperature. When used as the host material of a light-emitting layer, its high triplet energy level allows for efficient energy transfer from the host material to the guest material, reducing energy return and thus increasing the light emission efficiency of the OLED device. The condensed polycyclic compound is characterized by a high glass transition temperature, high thermal and morphological stability, and excellent film formation behavior. As a host material of a light-emitting layer, it is not easily crystallized, which contributes to improved performance and light emission efficiency of the OLED device. 2. In the condensed polycyclic compound according to the invention, the substituted groups R1, R2, R are adjusted. 1a to R 7aAr1 allows the introduction of an electron-withdrawing group (pyridine group, pyrimidine group, triazine group, pyrazine group, oxadiazole group, thiadiazole group, quinazoline group, imidazole group, quinoxaline group, quinoline group, etc.) or an electron-donating group (diphenylamine group, triphenylamine group, fluorene group, etc.) into the substituted group. The HOMO energy level is distributed around the electron-donating group, while the LUMO energy level is distributed around the electron-withdrawing group, thus further improving the hole and electron conduction behavior of the material's molecules and achieving a more balanced charge transfer.When used as the host material of a light-emitting layer, the recombination range for holes and electrons is further increased, and the exciton concentration per unit volume is reduced, thus preventing triplet exciton concentration annihilation due to high concentration or triplet-triplet exciton annihilation. The inclusion of an electron-donating group and an electron-withdrawing group raises the HOMO energy level of the condensed polycyclic compound and lowers the LUMO energy level. Furthermore, when used as the host material of a light-emitting layer, it contributes to the matching of adjacent hole-based and electron-based charge carrier functional layers.

[0024] As from Fig. 1 (at the in Fig.As can be seen from Figure 1, the compound shown is the condensed polycyclic compound according to D-2. In the condensed polycyclic compound, the HOMO energy level and the LUMO energy level are effectively separated from each other by distributing HOMO and LUMO to different electron-donating and electron-withdrawing groups. This reduces the difference ΔEst (≤ 0.3 eV) between the singlet and triplet energy levels of the molecules of the material, which contributes to reverse intersystem crossing of triplet excitons to singlet excitons, promotes Förster energy transfer from the host material to the guest material, and reduces the loss during energy transfer.

[0025] By providing an electron-donating group, an electron-withdrawing group, and their spatial positions, a rigid and twisted molecular configuration is achieved, and intermolecular conjugation is established, thereby increasing the triplet energy level of the material's molecules and resulting in a low ΔEst value. Conversely, by providing L and Ar1, the electron-donating and electron-withdrawing groups, as well as the distance between them, are adjusted, enabling a more uniform distribution of the LUMO or HOMO energy levels and further optimizing the HOMO and LUMO energy levels. 3. The inventive process for producing a condensed polycyclic compound is characterized by readily available starting material, moderate reaction conditions and simple steps, thus providing a simple and easily implemented manufacturing process for the mass production of the condensed polycyclic compound. 4. In the organic electroluminescent device (OLED) according to the invention, the condensed polycyclic compound is contained in at least one functional layer, wherein the functional layer is a light-emitting layer.

[0026] In condensed polycyclic compounds (CPFCs), the electron and hole conduction behavior is balanced, resulting in increased recombination probability of electrons and holes in the light-emitting layer. Furthermore, CPFCs exhibit a high triplet energy level, which promotes energy transfer from the host material to the guest material and prevents energy feedback. The high glass transition temperature of CPFCs prevents crystallization of the CPFC material molecules, thus improving the performance of the OLED device.

[0027] By adjusting the substituted group, the hole and electron conduction behavior of the condensed polycyclic compound is improved, resulting in a more balanced charge and hole conduction in the light-emitting layer. This increases the region in the light-emitting layer where holes and electrons recombine into electrons, reduces the exciton concentration, prevents triplet-triplet annihilation of the device, and thus increases the device's efficiency. Furthermore, the recombination region of the charge carriers is kept away from the interface between the light-emitting layer and the hole or electron conduction layer, thereby increasing the color purity of the OLED device, preventing exciton feedback to the conduction layer, and further enhancing the device's efficiency.

[0028] In the condensed polycyclic compound, the HOMO and LUMO energy levels of the material molecules are adjusted by means of the electron-donating and electron-withdrawing groups, thus reducing the superposition of HOMO and LUMO energy levels and resulting in condensed rings exhibiting a ΔEst value. This promotes reverse intersystem crossing (RISC), in which triplet excitons are converted into singlet excitons, suppresses Dexter energy transfer (DET) from the host material to the light-emitting dye, promotes Förster energy transfer, effectively reduces energy loss during DET and the efficiency drop of the organic electroluminescence device, and increases the external quantum efficiency of the device. PRESENTATION OF THE IMAGES

[0029] To better explain the embodiments according to the present invention or the embodiments in the prior art, the accompanying drawings used in the embodiments are briefly described below, whereby it is understood that the following drawings only represent some embodiments of the invention and that it is possible for persons skilled in the art in this field to obtain further drawings from such drawings without inventive activity.

[0030] This shows Fig. 1 the theoretical calculation result of the HOMO energy level, the LOMO energy level and the ΔEst value of the condensed polycyclic compound according to D-2, which is produced in a first embodiment, Fig.2 the organic electroluminescence device according to the seventh to twelfth embodiments and a first comparative example of the present invention in a schematic structural representation. Description of the reference symbols:

[0031] 1-Anode, 2-Hole injection layer, 3-Hole conduction layer, 4-Light-emitting layer, 5-Electron conduction layer, 6-Electron injection layer, 7-Cathode. SPECIFIC FORMS OF EXECUTION

[0032] The following are complete and clear explanations of embodiments of the present invention with reference to the accompanying drawings. It is understood that the described embodiments represent only a subset of the embodiments and not all embodiments of the invention. All other embodiments that could be obtained by a person skilled in the art in this field from the embodiments of the invention without inventive steps are also within the scope of protection of the invention.

[0033] In describing the present invention, it should be noted that the terms "first", "second" and "third" are not to be understood as an implicit or explicit indication of relative importance, but serve only for descriptive purposes.

[0034] The present invention can be implemented in various ways, and there is no limitation to the exemplary embodiments described. Rather, providing such exemplary embodiments serves to complete the present invention and to convey the basic ideas of the invention to those skilled in the art in this field, the scope of the present invention being defined by the claims. In the accompanying drawings, the size and relative size of the layer and the region are enlarged where necessary for clarity. It is understood that an element formed or arranged on another element, for example a layer, can be arranged either directly on the other element or via an interposed element. In contrast, an element formed or arranged directly on another element does not involve an interposed element. First embodiment

[0035] The present embodiment provides a condensed polycyclic compound having the structure according to formula D-2:

[0036] The condensed polycyclic compound of formula D-2 is synthesized via the following synthesis route:

[0037] The process for preparing the condensed polycyclic compound according to formula D-2 comprises the following steps: - (1) Synthesize an intermediate 1-1, 9.1 g (50 mmol) of compound of formula (A-1), 7.8 g (25 mmol) of 2,2'-dibromobiphenyl (compound of formula (B-1)), 200 mL of 1,4-dioxane, 48 mg of copper(I) iodide (0.25 mmol), 3.5 g of sodium ter-butoxide (36 mmol), and 0.3 mL of cis-1,2-cyclohexanediamine are placed in a 500 mL three-necked flask under a nitrogen atmosphere. After reacting at 100 °C for 12 hours, the mixture is extracted three times with trichloromethane. The solvent is then removed by rotary evaporation, and 6.2 g of intermediate 1-1 are obtained in the solid state by silica gel column chromatography (yield 60%). - (2) Synthesize an intermediate 2-1, Weigh out 4.13 g of intermediate 1-1 (10 mmol), 2.2 g of potassium ter-butoxide (23 mmol), and 500 mL of dimethyl sulfoxide under a nitrogen atmosphere and place in a 1 L three-necked flask. After the reaction, extract the liquid using methylbenzene for 2 hours under light exposure. Then remove the solvent by rotary evaporation and obtain 1.7 g of intermediate 2-1 in solid state by silica gel column chromatography (yield 50%). - (3) Synthesizing a condensed polycyclic compound D-2: Add 1.7 g of intermediate 2-1 (5 mmol), 1.6 g of compound (6 mmol), 1.7 g of cesium carbonate (5 mmol), 0.3 g of 4-dimethylaminopyridine (2.5 mmol) and 20 mL of dimethyl sulfoxide under a nitrogen protective atmosphere, after reaction at 100 °C for 3 hours cool to room temperature, then extract using methylbenzene, remove the solvent by rotary evaporation and obtain 2.3 g of condensed polycyclic compound D-2 in solid state by silica gel column chromatography (yield 85%).

[0038] Elemental analysis: (C38H24N4); Theoretical value: C, 85.05; H, 4.51; N, 10.44; Measured value: C, 85.01; H, 4.53; N, 10.45, HRMS (ESI) m / z (M+): Theoretical value: 536.20; Measured value: 536.23. Second embodiment

[0039] The present embodiment provides a condensed polycyclic compound having the structure according to formula D-1:

[0040] The condensed polycyclic compound of formula D-1 is synthesized via the following synthesis route:

[0041] The process for preparing the condensed polycyclic compound according to formula D-1 comprises the following steps: - (1) Synthesize an intermediate product 2-1 using the synthesis method according to the first embodiment, - (2) Synthesize a condensed polycyclic compound D-1 Add 1.7 g of compound 1-2 (5 mmol), 0.03 g of palladium acetate (0.15 mmol), 0.1 g of tri-tert-butylphosphine (0.55 mmol), 2 g of compound (5.1 mmol), 1.41 g of sodium ter-butoxide and 750 mL of methylbenzene under a nitrogen protective atmosphere, after reaction at 110 °C for 12 hours and cooling to room temperature, extract using chloroform, remove the solvent by rotary evaporation and obtain 2.6 g of compound C-16 in solid state by silica gel column chromatography (yield 81%).

[0042] Elemental analysis: (C45H29N5); Theoretical value: C, 84.48; H, 4.57; N, 10.95; Measured value: C, 84.50; H, 4.55; N, 10.96, HRMS (ESI) m / z (M+): Theoretical value: 639.24; Measured value: 639.27. Third example

[0043] The present embodiment provides a condensed polycyclic compound having the structure according to formula D-7:

[0044] The condensed polycyclic compound of formula D-7 is synthesized via the following synthesis route:

[0045] The process for the preparation of the condensed polycyclic compound according to formula D-7 comprises the following: - (1) Synthesize an intermediate 3-1, Place 5.6 g of compound (20 mmol) of formula (C-1), 3.5 g of 3-chloride-2-fluoronitrobenzene (compound of formula (E-1)) (20 mmol), 7.8 g of cesium carbonate (24 mmol) and 80 mL of dimethyl sulfoxide into a 500 mL three-necked flask under a nitrogen atmosphere, extract the mixture for 15 hours using methylbenzene, remove the solvent by rotary evaporation and obtain 6.5 g of intermediate 3-1 in solid state by silica gel column chromatography (yield 75%). - (2) Synthesize an intermediate product 4-1, Add 4.3 g of intermediate 3-1 (10 mmol), 0.2 g of palladium acetate (1.0 mmol), 0.73 g of tricyclohexylphosphonium tetrafluoroborate (2.0 mmol), 9.7 g of cesium carbonate (30 mmol) and 50 mL of ortho-xylene under a nitrogen atmosphere. After reaction, extract using chloroform by heating and refluxing for 2 hours, remove the solvent by rotary evaporation, and obtain 2.8 g of intermediate 4-1 in solid state by silica gel column chromatography (yield 75%). - (3) Synthesize an intermediate product 5-1, Add 2.8 g of intermediate 4-1 (7 mmol), 6.3 g of tin(II) chloride dihydrate (28 mmol), 5 mL of hydrochloric acid, and 40 mL of ethanol under a nitrogen atmosphere. After reaction, extract using chloroform at 60 °C for 10 hours, rinse with water, rinse with salt, dry with anhydrous magnesium sulfate, remove the solvent by rotary evaporation, transfer to a reaction flask after drying, add 64 mg of tris(dibenzylideneacetone)dipalladium (0.07 mmol) and 50 mL of methylbenzene, after reaction at 110 °C for 8 hours to room temperature, extract using chloroform, rinse with water, remove the solvent by rotary evaporation, and obtain 1.68 g of intermediate 5-1 in solid state by silica gel column chromatography (yield 71%). - (4) Synthesize a condensed polycyclic compound D-7 Add 1.65 g of intermediate 5-1 (5 mmol), 0.03 g of palladium acetate (0.15 mmol), 0.1 g of tri-tert-butylphosphine (0.55 mmol), 2 g of compound (5.1 mmol), 1.41 g of sodium ter-butoxide and 750 mL of methylbenzene under a nitrogen protective atmosphere, after reaction at 110 °C for 12 hours and cooling to room temperature, extract using chloroform, remove the solvent by rotary evaporation and obtain 2.5 g of condensed polycyclic compound D-7 in solid state by silica gel column chromatography (yield 79%).

[0046] Elemental analysis: (C45H27N5); Theoretical value: C, 84.75; H, 4.27; N, 10.98; Measured value: C, 84.78; H, 4.25; N, 11.01, HRMS (ESI) m / z (M+): Theoretical value: 637.23; Measured value: 637.41. Fourth embodiment

[0047] The present embodiment provides a condensed polycyclic compound having the structure according to formula D-8:

[0048] The condensed polycyclic compound of formula D-8 is synthesized via the following synthesis route:

[0049] The process for the preparation of the condensed polycyclic compound according to formula D-18 comprises the following steps: - (1) Synthesize an intermediate product 5-1 using the synthesis method according to the third embodiment, - (2) Synthesize a condensed polycyclic compound D-8, add 1.65 g intermediate 5-1 (5 mmol), 1.6 g compound (6 mmol), 1.7 g cesium carbonate (5 mmol), 0.3 g 4-dimethylaminopyridine (2.5 mmol) and 20 mL dimethyl sulfoxide under a nitrogen protective atmosphere, after reaction at 100 °C for 3 hours cool to room temperature, then extract using methylbenzene, remove the solvent by rotary evaporation and obtain 2.2 g of compound D-8 in solid state by silica gel column chromatography (yield 83%).

[0050] Elemental analysis: (C38H22N4); Theoretical value: C, 85.37; H, 4.15; N, 10.48; Measured value: C, 85.34; H, 4.21; N, 10.53, HRMS (ESI) m / z (M+): Theoretical value: 534.18; Measured value: 534.32. Fifth embodiment

[0051] The present embodiment provides a condensed polycyclic compound having the structure according to formula D-5:

[0052] The condensed polycyclic compound of formula D-5 is synthesized via the following synthesis route:

[0053] The process for preparing the condensed polycyclic compound according to formula D-5 comprises the following steps: -(1) Synthesize an intermediate 3'-1, 12.2 g of compound (50 mmol) of formula (C'-1), 8.8 g of 3-chloride-2-fluoronitrobenzene (compound of formula E'-1) (50 mmol), 19.5 g of cesium carbonate (60 mmol) and 200 mL of dimethyl sulfoxide are placed in a 500 mL three-necked flask under a nitrogen atmosphere. After reaction, the mixture is extracted for 15 hours using methylbenzene. The solvent is removed by rotary evaporation, and 14.3 g of intermediate 3'-1 are obtained in the solid state by silica gel column chromatography (yield 72%). - (2) Synthesize an intermediate 4'-1, Add 12 g of intermediate 3'-1 (30 mmol), 0.6 g of palladium acetate (3.0 mmol), 2.2 g of tricyclohexylphosphonium tetrafluoroborate (6.0 mmol), 29.1 g of cesium carbonate (90 mmol) and 150 mL of ortho-xylene under a nitrogen atmosphere, after reaction by heating and refluxing for 2 hours using chloroform, remove the solvent by rotary evaporation and obtain 8.2 g of intermediate 4'-1 in solid state by silica gel column chromatography (yield 75%). - (3) Synthesize an intermediate 5'-1, Add 2.8 g of intermediate 4'-1 (21 mmol), 18.9 g of tin(II) chloride dihydrate (84 mmol), 15 mL of hydrochloric acid, and 120 mL of ethanol under a nitrogen atmosphere. After reaction, extract using chloroform at 60 °C for 10 hours, rinse with water, rinse with salt, dry with anhydrous magnesium sulfate, remove the solvent by rotary evaporation, transfer to a reaction flask after drying, add 0.19 g of tris(dibenzylideneacetone)dipalladium (0.21 mmol) and 150 mL of methylbenzene, after reaction at 110 °C for 8 hours to room temperature, extract using chloroform, rinse with water, remove the solvent by rotary evaporation, and obtain 5.13 g of intermediate 5'-1 in solid state by silica gel column chromatography (yield). 71%), - (4) Synthesize a condensed polycyclic compound D-5, add 3.3g intermediate 5'-1 (10 mmol), 3.2g compound (12 mmol), 3.4g cesium carbonate (10 mmol), 0.6g 4-dimethylaminopyridine (5.0 mmol) and 40 mL dimethyl sulfoxide under a nitrogen protective atmosphere, after reaction at 100 °C for 3 hours cool to room temperature, then extract using methylbenzene, remove the solvent by rotary evaporation and obtain 4.6g of condensed polycyclic compound D-5 in solid state by silica gel column chromatography (yield 85%).

[0054] Elemental analysis: (C37H23N5); Theoretical value: C, 82.66; H, 4.31; N, 13.03; Measured value: C, 82.68; H, 4.28; N, 13.01, HRMS (ESI) m / z (M+): Theoretical value: 537.20; Measured value: 535.27. Sixth embodiment

[0055] The present embodiment provides a condensed polycyclic compound having the structure according to formula D-6:

[0056] The condensed polycyclic compound of formula D-6 is synthesized via the following synthesis route:

[0057] The process for the preparation of the condensed polycyclic compound according to formula D-6 comprises the following: - (1) Using the compound of formula (C'-2) and the compound (E'-1) as raw materials, synthesize the intermediate 5'-2 using the synthesis method according to the fifth embodiment, - (2) Synthesize a condensed polycyclic compound D-6, add 5.6g intermediate 5'-1 (16.7 mmol), 5.5g compound (17mmol), 0.11g palladium acetate (0.5 mmol), 0.37g tri-tert-butylphosphine (1.83 mmol), 4.7g sodium ter-butoxide and 250 mL methylbenzene under a nitrogen protective atmosphere, after reaction at 110°C for 12 hours cool to room temperature, then extract using methylbenzene, remove the solvent by rotary evaporation and obtain 8.2g of condensed polycyclic compound D-6 in solid state by silica gel column chromatography (yield 85%).

[0058] Elemental analysis: (C40H25N5); Theoretical value: C, 83.46; H, 4.38; N, 12.17; Measured value: C, 83.42; H, 4.41; N, 12.14, HRMS (ESI) m / z (M+): Theoretical value: 575.21; Measured value: 575.27. Seventh embodiment

[0059] The present embodiment provides an organic electroluminescent device comprising an anode 1, a hole injection layer 2, a hole conduction layer 3, a light-emitting layer 4, an electron conduction layer 5, an electron injection layer 6, and a cathode 7, arranged one above the other from bottom to top, as shown in the figure. Fig. 2 can be seen.

[0060] In the organic electroluminescence device, the ITO material is preferably used as the anode and the metal Al as the cathode 7.

[0061] HAT(CN)6, which has the following chemical structure, is used as the material for the hole injection layer 2:

[0062] The material used for the hole conduction layer 3 is the compound with the following structure:

[0063] The material used for the electron conduction layer 5 is the compound with the following structure:

[0064] The material of the electron injection layer 6 is formed by doping the following compound with the electron injection material LiF:

[0065] The material of the light-emitting layer 32 in the organic electroluminescent device is formed by doping a host material with a guest material, wherein the host material is a condensed polycyclic compound (D-2) and the guest material is compound RD, and the mass ratio of the host material to the guest material at doping is 100:5. The following specific structure is formed for the organic electroluminescent device: ITO / hole injection layer (HIL) / hole conduction layer (HTL) / organic light-emitting layer (condensed polycyclic compound D-2 doped with compound RD) / electron conduction layer (ETL) / electron injection layer (EIL / LiF) / cathode (A1). The condensed polycyclic compound D-2 and the compound RD have the following chemical structures:

[0066] The host material used in the light-emitting layer is the condensed polycyclic compound of formula D-2. The effective conjugation of this compound is enhanced by the specific configuration of the condensation of an aromatic ring and a heterocycle in the parent core structure. This not only improves the compound's hole properties but also helps to balance its electron conduction behavior. The condensed polycyclic compound of formula D-2 exhibits a high triplet energy level and a high glass transition temperature, ensuring efficient energy transfer from the host material to the guest material and preventing crystallization of the light-emitting layer material molecules.Furthermore, the compound exhibits a double dipolarity, and the HOMO and LUMO energy levels of the host material are positioned at different electron-donating and electron-withdrawing groups (quinazoline). This results in a balanced hole and electron conduction behavior in the host material, increases the area in the light-emitting layer where holes and electrons recombine into electrons, reduces the exciton concentration, prevents triplet-triplet annihilation of the device, and thus increases the device's efficiency.In addition, the recombination area of ​​the charge carriers in the host material is kept away from the interface between the light-emitting layer and the hole or electron conduction layer, thereby increasing the color purity of the OLED device, avoiding the return of excitons to the conduction layer and further increasing the efficiency of the device.

[0067] With respect to the HOMO energy level and the LUMO energy level, the condensed polycyclic compound D-2 is matched to the adjacent hole and electron conduction layer, so that the OLED device has a low drive voltage.

[0068] The HOMO energy level and the LUMO energy level of the condensed polycyclic compound D-2 are separated from each other, resulting in a small difference (ΔE). st) between the singlet and triplet energy levels, and reverse intersystem crossing of triplet excitons to singlet excitons is promoted. On the other hand, with a high rate of reverse intersystem crossing (RISC) from the triplet T1 to the singlet S1 of the host material, Dexter energy transfer (DET) from the host material to the light-emitting dye can be suppressed, Förster energy transfer promoted, the exciton loss of Dexter energy transfer (DET) avoided, the efficiency drop of the organic electroluminescence device prevented, and the light emission efficiency of the device increased.

[0069] In an alternative embodiment, a condensed polycyclic compound of one of the formulas (D-1) to (D-21) can also be used as the host material of the light-emitting layer. Eighth example

[0070] The present embodiment provides an organic electroluminescent device, the difference being that, compared to the organic electroluminescent device according to the seventh embodiment, the condensed polycyclic compound with the following structure is used as the host material of the light-emitting layer: Ninth embodiment

[0071] The present embodiment provides an organic electroluminescent device, the difference being that, compared to the organic electroluminescent device according to the seventh embodiment, the condensed polycyclic compound with the following structure is used as the host material of the light-emitting layer: Tenth embodiment

[0072] The present embodiment provides an organic electroluminescent device, the difference being that, compared to the organic electroluminescent device according to the seventh embodiment, the condensed polycyclic compound with the following structure is used as the host material of the light-emitting layer: Eleventh embodiment

[0073] The present embodiment provides an organic electroluminescent device, the difference being that, compared to the organic electroluminescent device according to the seventh embodiment, the condensed polycyclic compound with the following structure is used as the host material of the light-emitting layer: Twelfth embodiment

[0074] The present embodiment provides an organic electroluminescent device, the difference being that, compared to the organic electroluminescent device according to the seventh embodiment, the condensed polycyclic compound with the following structure is used as the host material of the light-emitting layer: First comparison example

[0075] The present comparative example provides an organic electroluminescent device, the difference being that, compared to the organic electroluminescent device according to the seventh embodiment, 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (referred to as CBP) is used as the host material of the light-emitting layer. First test example 1. Determining the glass transition temperature

[0076] The glass transition temperature of the material according to the invention was determined using a differential scanning calorimeter (DSC) under a nitrogen atmosphere at room temperature up to 400 °C with a heating rate of 10 °C / min.

[0077] 2. The phosphorescence and fluorescence spectrum of the methylbenzene solution of the condensed polycyclic compound (molecule concentration: 10 -5 The singlet (S1) and triplet (T1) energy levels were determined at temperatures of 298 K and 77 K, and the singlet / triplet energy level was calculated using the formula E = 1240 / λ, thus yielding the singlet / triplet energy level difference of the condensed polycyclic compound. The energy level difference of the condensed polycyclic compound can be found in Table 1 below. Table 1 Condensed polycyclic compound Formula D-2 Formula D-1 Formula D-7 Formula D-8 Formula D-5 Formula D-6 Glass transition temperature (°C) 158 162 169 161 160 165 T1 (eV) 2,74 2,72 2,67 2,70 2,65 2,68 S1-T1 (eV) 0,25 0,19 0,17 0,21 0,14 0,30 Second test example

[0078] The current, voltage, brightness, light emission spectrum, and other characteristics of the device were synchronously verified using the PR 650 spectrum-scanning luminance meter and the Keithley K 2400 source meter system. The organic electroluminescent device was checked according to embodiments seven through twelve and the first comparative example. The results are shown in Table 2. Table 2 Host material Voltage / V Current density / m A / cm2 Current yield cd / A Chrominance (CIE-X,Y) First comparison example CBP 5,1 10 21 (0,66, 0,23) Seventh embodiment D-2 4,1 10 27 (0,66, 0,23) Eighth example D-1 3,8 10 24 (0,66, 0,23) Ninth embodiment D-7 3,7 10 24 (0,66, 0,23) Tenth embodiment D-8 4,0 10 28 (0,66, 0,23) Eleventh embodiment D-5 3,2 10 24 (0,66, 0,23) Twelfth embodiment D-6 3,5 10 24 (0,66, 0,23)

[0079] The organic electroluminescent device according to the seventh to twelfth embodiments and the first comparative example was tested. The results are shown in Table 2. The light emission efficiency of the OLED device according to the seventh to twelfth embodiments is higher than that of the device according to the first comparative example, and the drive voltage is lower. This indicates that by using the condensed polycyclic compound according to the invention as the host material of the light-emitting layer of an OLED device, the light emission efficiency of the device can be effectively increased and the drive voltage of the device can be reduced.

[0080] It is understood that the foregoing embodiment merely represents an example for the sake of clarity, without limiting the possible embodiments. A person skilled in the art in this field could easily make other modifications or alterations to various forms based on the foregoing description. A complete listing of all possible embodiments is neither necessary nor possible here. Any obvious modifications or alterations that can be derived from it also fall within the scope of protection of the present invention.

Claims

[1] A condensed cyclic compound having a structure of formula (II): where X1 is selected from N or CR 1a , X2 is selected from N or CR 2a , X3 is selected from N or CR 3a , X4 is selected from N or CR 4a , X5 is selected from N or CR 5a , X6 is selected from N or CR 6a , and X7 is selected from N or CR 7a , where R 1a - R 7a independently of each other from hydrogen, halogen, cyano group, substituted or unsubstituted alkyl group from C1 to C 30 , substituted or unsubstituted alkenyl group from C2 to C 30 , substituted or unsubstituted alkynyl group from C2 to C 30 , substituted or unsubstituted naphthenic group from C3 to C 30 , substituted or unsubstituted alkoxy group from C1 to C 30, substituted or unsubstituted silane group from C1 to C 30 , substituted or unsubstituted aryl group from C6 to C 60 or substituted or unsubstituted heteroaryl group from C3 to C 30 be elected, R1 and R2 independently of each other are hydrogen, halogen, cyano group, substituted or unsubstituted alkyl group from C1 to C 30 , substituted or unsubstituted alkenyl group from C2 to C 30 , substituted or unsubstituted alkynyl group from C2 to C 30 , substituted or unsubstituted naphthenic group from C3 to C 30 , substituted or unsubstituted alkoxy group from C1 to C 30 , substituted or unsubstituted silane group from C1 to C 30 , substituted or unsubstituted aryl group from C6 to C 60 or substituted or unsubstituted heteroaryl group from C3 to C 30 be elected, Ar1is selected from one of the following groups, and R1, R2, R 1a , R 2a , R 3a , R 4a , R 5a , R6a and R7a are each independently selected from hydrogen or one of the following groups: wherein X is nitrogen, oxygen or sulfur, Y is each independently nitrogen or carbon; and in which at least one Y is nitrogen; and n is an integer from 0-5, m is an integer from 0-7, p is an integer from 0-6, q is an integer from 0-8 and t is an integer from 0-7; and is a single or double bond; R3 is each independently selected from hydrogen; and Ar3ist jeweils unabhängig ausgewählt aus, Coronenyl, Pentalenyl, Indenyl, Naphthyl, Azulenyl, Fluorenyl, Heptalenyl, Octalenyl, Benz odiindenyl, Acenaphthylenyl, Phenalenyl, Phenanthrenyl, Anthracenyl, Triindenyl, Fluoranthen yl,Benzopyrenyl,Benzoperylenyl,Benzofluoranthenyl,Acephenanthrenyl,Aceanthrylenyl, 9,10-Benzophenanthrenyl,Pyrenyl, 1,2-Benzophenanthrenyl, ,Naphthacenyl,Pleiadenyl,Picenyl,Perylenyl, ,Pentacenyl, ,Cholanthrenyl,Helicenyl, ,Rubicenyl, Coronenyl, Trinaphthylenyl, ‚Pyranthrenyl, Ovalenyl, Corannulenyl, Anthanthrenyl, Truxenyl, Pyranyl, Benzopyranyl, Furyl ,Benzofuryl, Isobenzofuryl, Oxanthracenyl, Oxazolinyl, Dibenzofuryl, Peri-Xanthenoxanthenyl, Thienyl, Thioxanthenyl, Thianthrenyl, Phenoxathiinyl, Thionaphthenyl, Is othionaphthenyl, Thiophanthrenyl, Dibenzothienyl, Benzothienyl, Pyrrolyl, Pyrazolyl, Telluraz olyl,Selenazolyl, Thiazolyl, Isothiazolyl, Oxazolyl, Oxadiazolyl, Furazanyl, Pyridinyl, Pyraziny 1, Pyrimidinyl, Pyridazinyl, Triazinyl, Indolizinyl, Indolyl,Isoindolyl, Indazolyl, Purinyl, Quinolizinyl, Isoquinolyl, Carbazolyl, Fluorenocarbazolyl, Indolocarbazolyl, Imidazolyl, Naphthyridinyl, Phthalazinyl, Quinazolinyl, Benzodiazepinyl, Quinoxalinyl, Cinnolinyl, Quinolyl, Pteridinyl, Phenanthridinyl,Acridinyl,Perimidinyl,Phenanthrolinyl,Phenazinyl,Carbolinyl,Phenotellura zinyl, Phenoselenazinyl, Phenothiazinyl, Phenoxazinyl, Triphenodithiazinyl, Azadibenzofuryl, Triphenodioxazinyl, Anthrazinyl, Benzothiazolyl, Benzoimidazolyl, Benzoxazolyl, benzisoxa zolyl or benzoisothiazolyl; and, L is a single bond, a substituted or unsubstituted aliphatic C1-C10 hydrocarbon group, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group, wherein the heteroaryl has at least one heteroatom independently selected from nitrogen, sulfur, oxygen, phosphorus, boron, or silicon. [2] A condensed cyclic compound according to claim 1 having the molecular structure shown below: [3] A process for producing a condensed cyclic compound according to claim 1 or 2, wherein the compound of formula (II) is synthesized by the following steps: Subjecting a compound of formula (C) and a compound of formula (E) in a molar ratio of 1:1 as starting materials to a coupling reaction for 15 hours in the presence of a catalyst to obtain an intermediate 3; cyclizing the intermediate 3 for 2 hours to obtain an intermediate 4; reducing the nitro group of the intermediate 4 with tin(II) chloride dihydrate in a molar ratio of 1:4 of the intermediate 4 to tin(II) chloride dihydrate at 60°C for 10 hours and then subjecting the intermediate 4 to a coupling reaction with tris(dibenzylideneacetone) dipalladium at 110°C for 8 hours to obtain an intermediate 5; and subjecting the intermediate 5 and a compound T3-L-Ar1 to a substitution or coupling reaction at 110 °C for 12 hours in the presence of a catalyst to obtain the compound of formula (II), where the synthesis route for the compound of formula (II) is shown below: wherein T3-T6 are each independently selected from hydrogen, fluorine, chlorine, bromine or iodine. [4] A process for producing a condensed cyclic compound according to claim 1 or 2, wherein the compound of formula (II) is synthesized by the following steps: subjecting a compound of formula (C') and a compound of formula (E') in a molar ratio of 1:1 as starting materials to a coupling reaction for 15 hours in the presence of a catalyst to obtain an intermediate 3'; cyclizing the intermediate 3' for 2 hours to obtain an intermediate 4'; reducing the nitro group of the intermediate 4' with tin(II) chloride dihydrate in a molar ratio of 1:4 of the intermediate 4 to tin(II) chloride dihydrate at 60°C for 10 hours and then subjecting the intermediate 4' to a coupling reaction with tris(dibenzylideneacetone)-dipalladium at 110°C for 8 hours to obtain an intermediate 5'; and subjecting the intermediate 5' and a compound T3-L-Ar1 to a substitution or coupling reaction at 110 °C for 12 hours in the presence of a catalyst to obtain the compound of formula (II); where the synthesis route for the compound of formula (II) is shown below: wherein T1-T3 are each independently selected from hydrogen, fluorine, chlorine, bromine or iodine. [5] Use of a condensed cyclic compound according to claim 1 or 2 as an organic electroluminescent material. [6] An organic light-emitting device comprising at least one functional layer containing a condensed cyclic compound according to claim 1 or 2. [7] The organic light-emitting device according to claim 6, wherein the functional layer is a light-emitting layer. [8] The organic light-emitting device according to claim 7, wherein the material of the light-emitting layer comprises a host material and a guest luminescent dye, wherein the host material is the condensed cyclic compound.

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  • Heterocyclic compounds with dibenzazapine strctures

    CN107108623A