CN-121405734-B - Organic compound containing boron and nitrogen and organic electroluminescent device containing same

Abstract

The invention relates to the technical field of semiconductors, and provides a boron-nitrogen-containing organic compound and an organic electroluminescent device comprising the same. The organic electroluminescent device provided by the invention adopts the doping material with a specific structure, and introduces the specific doping material containing B, N atoms, because the boron atoms have empty p orbits, the doping material can be used as a strong electron acceptor, and the effective capture and transmission of electrons in molecules are promoted, so that the overall carrier balance is improved, the electron injection and transmission efficiency of the device can be enhanced by introducing the specific structure with the formula 1 or the formula 2, the electron mobility of the device can be improved, and finally the reduction of the driving voltage, the improvement of the efficiency and the prolongation of the service life of the OLED device are realized.

Inventors

• WANG HUI
• LI XIAOLONG
• LI GUOQIANG
• LANG XINGWANG
• SHAO JIAN
• XU WEIHAN

Assignees

• 吉林奥来德光电材料股份有限公司

Dates

Publication Date

20260512

Application Date

20251229

Claims (6)

1. 1. The boron-nitrogen-containing organic compound is characterized by comprising one of the following specific structures: ; x is one of NR ́, O, S, si R ́ R ́ ́, ge R ́ R ́ ́, C R ́ R ́ ́ and Se; Y is NR ́ or C R ́ R ́ ́; Wherein R ́ and R ́ ́ are each independently selected from one or more of -H、-D、-T、-F、-CN、-CH 3 、-CD 3 、-CT 3 、-CF 3 、-CH 2 F、-CHF 2 、-SiMe 3 、-GeMe 3 、 unsubstituted C2-C40 alkyl, unsubstituted C3-C40 cycloalkyl, unsubstituted C6-C40 aryl, unsubstituted C4-C40 heterocyclyl; R 1 -R 7 、Ar 1 、Ar 2 、Ar 3 and Ar 4 are each independently selected from the group consisting of ：-H、-D、-T、-F、-CN、-CH 3 、-CD 3 、-CT 3 、-CF 3 、-CH 2 F、-CHF 2 、-SiMe 3 、-GeMe 3 、 methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, phenyl, biphenyl, deuterated phenyl, dideugenol, benzidine, naphthyl, fluorenyl, phenanthryl, anthracenyl, indenyl, triphenylenyl, pyrenyl, naphthacene, perylenyl, droyl, fused tetraphenyl, fluoranthenyl, furanyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, aziridinyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, indolinyl, benzisoxazolyl, quinoxalinyl, benzisoxazolyl, and combinations thereof: ; And, one of R 1 -R 7 、Ar 1 、Ar 2 、Ar 3 and Ar 4 contains at least one or both of formula 1 and formula 2; ; Wherein, the Representing the connection location; x 1 is independently selected from one of Si and C; X 2 is independently selected from one of Si and C; When X 1 is Si, X 2 is C, which is not included in the above formula; X3 is selected from one of O, S, se; Y 1 and Y 2 are each independently selected from SiRxRy, ge RxRy; wherein Rx and Ry are independently selected from one or more of -H、-D、-T、-F、-CN、-CH 3 、-CD 3 、-CT 3 、-CF 3 、-CH 2 F、-CHF 2 、-SiMe 3 、-GeMe 3 、 unsubstituted C2-C18 alkyl, unsubstituted C3-C40 cycloalkyl, unsubstituted arylamine, unsubstituted C6-C40 aryl, unsubstituted C4-C40 heterocyclyl; the ring A is selected from one or more of unsubstituted C3-C40 cycloalkyl, unsubstituted C6-C40 aryl and unsubstituted C2-C40 heteroaryl; The ring M1-ring M7 is selected from the group consisting of phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, benzophenanthryl, biphenyl, terphenyl, dimethylfluorenyl, diphenylfluorenyl, pyridyl, carbazolyl, furanyl, pyrimidinyl, pyrazinyl, pyridazinyl, thienyl, dibenzofuranyl, dibenzothienyl, 9-dimethylfluorenyl, N-phenylcarbazolyl, quinolinyl, isoquinolinyl, naphthyridinyl, oxazolyl, imidazolyl, benzoxazolyl, benzimidazolyl cyclopentyl, cyclohexane, adamantyl, 9-diphenylfluorenyl, spirofluorenyl, and combinations thereof; The square H is one or more of phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylene, fluoranthryl, dibenzofuranyl and dibenzothienyl; Indicating no connection or connection.
2. 2. The boron-nitrogen-containing organic compound according to claim 1, wherein R 1 -R 7 、Ar 1 、Ar 2 、Ar 3 and Ar 4 form a substituted or unsubstituted C3-C40 aliphatic ring, a substituted or unsubstituted C6-C40 aromatic ring, a substituted or unsubstituted C4-C40 aromatic heterocyclic ring, a substituted or unsubstituted C10-C40 fused ring with each other or with other substituents on the ring; the substituent is at least one or more selected from -H、-D、-T、-F、-CN、-CH 3 、-CD 3 、-CT 3 、-CF 3 、-CH 2 F、-CHF 2 、-SiMe 3 、-GeMe 3 ; The hetero atom in the aromatic heterocyclic group is one or more of N, O, S, se, si, ge; The hydrogen in the group is substituted with deuterium or unsubstituted.
3. 3. A boron-nitrogen-containing organic compound, characterized in that the boron-nitrogen-containing organic compound has one of the specific structures shown in the following formula: 。
4. 4. An organic electroluminescent device, characterized in that the organic electroluminescent device comprises an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a luminescent layer, an electron transport layer, an electron injection layer and a cathode which are sequentially arranged, wherein the doping material of the luminescent layer is the boron-nitrogen-containing organic compound as claimed in claim 1.
5. 5. The organic electroluminescent device according to claim 4, wherein the light-emitting layer comprises a first host material, a second host material, and a doping material, the doping material being the boron-nitrogen-containing organic compound according to claim 1.
6. 6. The organic electroluminescent device according to claim 4, wherein the light-emitting layer comprises a host material, an exciton-sensitizing material which is a complex containing a metal element, and a doping material which is the boron-nitrogen-containing organic compound according to claim 1.

Description

Organic compound containing boron and nitrogen and organic electroluminescent device containing same Technical Field The invention relates to the technical field of semiconductors, in particular to a boron-nitrogen-containing organic compound and an organic electroluminescent device comprising the same. Background An Organic Light Emitting Diode (OLED) is an electroluminescent device based on an organic semiconductor material, and its operating principle is to realize light emission by driving carrier injection and recombination by an electric field. OLEDs can be divided into single layer, double layer, triple layer, and multi-layer devices depending on their structure. Among them, the multi-layered structure is most advantageous because it can finely control the function of each layer (e.g., charge transport, light emission, etc.), thereby improving light emission efficiency, color expression, and device lifetime. The design flexibility enables the OLED to be widely applied to the fields of mobile phones, televisions, flexible display screens and the like. With the advent of the 5G age, higher requirements are put on the color development standard, and besides high efficiency and stability, the luminescent material also needs narrower half-peak width to improve the luminescent color purity of the device. The fluorescent doped material can realize high fluorescence quantum and narrow half-peak width through molecular engineering, the blue fluorescent doped material has obtained a stepwise breakthrough, the half-peak width of the boron material can be reduced to below 30nm, and the research is mainly focused on a green light region which is more sensitive to human eyes, but the luminous peak shape of the fluorescent doped material is difficult to narrow through a simple method, so that the research on the high-efficiency green fluorescent doped material with the narrow half-peak width has important significance for meeting higher color development standards. In addition, the sensitization technology combines the triplet state exciton sensitization material and the fluorescent doping material, the triplet state exciton sensitization material is used as an exciton sensitization medium, the triplet state exciton is fully utilized, energy is transferred to the fluorescent doping material through energy transfer, the internal quantum efficiency of the device can be 100%, the defect of insufficient utilization rate of the exciton of the fluorescent doping material can be overcome, the characteristics of high fluorescence quantum yield, high device stability, high color purity and low price of the fluorescent doping material can be effectively exerted, and the method has wide prospect in application of OLEDs. The boron compound with a resonance structure can easily realize narrow half-peak width luminescence, and the material is applied to sensitized fluorescence technology, so that the preparation of a device with high efficiency and narrow half-peak width emission can be realized. Therefore, the development of sensitization technology based on narrow half-peak width boron luminescent materials has unique advantages and strong potential in the index display of BT.2020. For organic electroluminescent devices with different structures, the used photoelectric functional materials have stronger selectivity, and the performance of the same materials in devices with different structures can be completely different. Therefore, aiming at the industrial application requirement of the current organic electroluminescent device and the requirements of different functional film layers of the organic electroluminescent device, the photoelectric characteristic requirement of the device must be developed and selected to be more suitable, and functional materials or material combinations with high performance can be realized to realize the comprehensive characteristics of high efficiency, long service life and low voltage of the device. Disclosure of Invention In view of the above, an object of the present invention is to provide a boron-nitrogen-containing organic compound and an organic electroluminescent device including the same. It should be noted that, the organic electroluminescent device provided by the invention adopts the doping material with a specific structure, and introduces the specific doping material containing B, N atoms, because the boron atoms have empty p orbits, the boron atoms can be used as strong electron acceptors, and promote the effective capture and transmission of electrons in molecules, so that the overall carrier balance is improved, the electron injection and transmission efficiency of the organic electroluminescent device can be enhanced by introducing the specific structure of formula 1 or formula 2, and meanwhile, the electron mobility of the organic electroluminescent device can be improved, and finally, the reduction of the driving voltage, the improvement of the efficiency and the prolongatio