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CN-121991037-A - Nitrogen-containing heterocyclic compound and organic electroluminescent device comprising same

CN121991037ACN 121991037 ACN121991037 ACN 121991037ACN-121991037-A

Abstract

The invention discloses a compound with a nitrogen-containing heterocyclic structure and an organic electroluminescent device containing the same, and belongs to the technical field of semiconductor materials. The structure of the compound is shown as a general formula (1), The compound of the invention has good stability and electron tolerance, and simultaneously has good electron injection and electron transmission capability, when the compound is used as an electron transport material of an organic electroluminescent device, the driving voltage of the device is obviously reduced, and the service life of the device is obviously improved.

Inventors

  • YU HAO
  • WANG FANG
  • LI CHONG

Assignees

  • 江苏三月科技股份有限公司

Dates

Publication Date
20260508
Application Date
20241107

Claims (10)

  1. 1. The compound with the nitrogen-containing heterocyclic structure is characterized in that the structure of the compound is shown as a general formula (1): In the general formula (1), X 1 to X 3 are each independently represented by a nitrogen atom or C-H, and at least one is represented by a nitrogen atom; Wherein X 1 to X 6 have at most five atoms represented as nitrogen atoms; R 1 、R 3 is independently represented by a hydrogen atom, phenyl substituted or unsubstituted by R a , naphthyl substituted or unsubstituted by R a , biphenyl substituted or unsubstituted by R a , dibenzofuranyl substituted or unsubstituted by R a ; R 2 represents a hydrogen atom, a phenyl group, a naphthyl group substituted or unsubstituted by R a , a biphenyl group substituted or unsubstituted by R a , a dibenzofuranyl group substituted or unsubstituted by R a ; One and only one of R 1 、R 2 、R 3 is not represented as a hydrogen atom; Ar 1 、Ar 2 may be the same or different and each independently represents a phenyl group substituted or unsubstituted by R b , a naphthyl group substituted or unsubstituted by R b , a biphenyl group substituted or unsubstituted by R b , a terphenyl group substituted or unsubstituted by R b , a pyridyl group substituted or unsubstituted by R b , a pyrimidinyl group substituted or unsubstituted by R b , or a dibenzofuranyl group substituted or unsubstituted by R b ; Ar 3 、Ar 4 may be the same or different and each independently represents a phenyl group substituted or unsubstituted by R c , a naphthyl group substituted or unsubstituted by R c , a biphenyl group substituted or unsubstituted by R c , a terphenyl group substituted or unsubstituted by R c , a pyridyl group substituted or unsubstituted by R c , a pyrimidinyl group substituted or unsubstituted by R c , or a dibenzofuranyl group substituted or unsubstituted by R c ; r a represents cyano, phenyl, biphenyl, terphenyl, pyridyl, pyrimidinyl; r b is phenyl, biphenyl, terphenyl, pyridyl, pyrimidinyl; r c represents cyano, phenyl, biphenyl, terphenyl, pyridyl, pyrimidinyl; At least one of Ar 3 、Ar 4 、R 1 、R 2 、R 3 is substituted with cyano.
  2. 2. The nitrogen-containing heterocyclic structure compound according to claim 1, wherein the structure of the compound is represented by any one of the general formulae (2-1) to (2-4): in the general formulae (2-1) to (2-4), the meaning of Ar 1 、Ar 2 、Ar 3 、Ar 4 、R 1 、R 2 、R 3 、X 1 、X 2 、X 3 is as defined in claim 1.
  3. 3. The nitrogen-containing heterocyclic structure compound according to claim 1, wherein the structure of the compound is represented by any one of the general formulae (3-1) to (3-4): In the general formulae (3-1) to (3-4), the meaning of Ar 1 、Ar 2 、Ar 3 、Ar 4 、R 1 、R 2 、R 3 、X 4 、X 5 、X 6 is as defined in claim 1.
  4. 4. The nitrogen-containing heterocyclic structure compound according to claim 1, wherein the structure of the compound is represented by any one of the general formulae (4-1) to (4-4): In the general formula (4-1) to the general formula (4-4), ar 1 、Ar 2 、Ar 3 、Ar 4 、R 1 、R 2 、R 3 has the same meaning as defined in claim 1.
  5. 5. The nitrogen-containing heterocyclic structure compound according to claim 1, wherein the structure of the compound is represented by any one of the general formulae (5-1) to (5-4): In the general formula (5-1) to the general formula (5-4), ar 1 、Ar 2 、Ar 3 、Ar 4 、R 1 、R 2 、R 3 has the same meaning as defined in claim 1.
  6. 6. The nitrogen-containing heterocyclic structure compound according to claim 1, wherein the structure of the compound is represented by any one of the general formulae (6-1) to (6-3): In the general formula (6-1) to the general formula (6-3), ar 1 、Ar 2 、Ar 3 、Ar 4 、R 1 、R 2 、R 3 has the meaning as defined in claim 1; Each of the X 1 to X 3 is independently represented as a nitrogen atom or C-H, and two or three are represented as nitrogen atoms; Each of the X 4 to X 6 is independently represented as a nitrogen atom or C-H, and two or three are represented as nitrogen atoms; Wherein X 1 to X 6 have four or five atoms represented as nitrogen atoms.
  7. 7. The nitrogen-containing heterocyclic compound according to claim 1, wherein the specific structure of the compound is any one of the following structures:
  8. 8. An organic electroluminescent device comprising a substrate, a first electrode and a second electrode, wherein a plurality of organic thin film layers are arranged between the first electrode and the second electrode, and the organic thin film layers comprise the nitrogen-containing heterocyclic compound according to any one of claims 1 to 7.
  9. 9. The organic electroluminescent device according to claim 8, wherein the organic thin film layer comprises a hole transport region thin film layer, a light emitting region thin film layer, and an electron transport region thin film layer containing the nitrogen-containing heterocyclic structure compound according to any one of claims 1 to 7; Preferably, the electron transport region thin film layer comprises an electron transport layer containing the nitrogen-containing heterocyclic compound according to any one of claims 1 to 7.
  10. 10. The organic electroluminescent device according to claim 9, wherein the hole transport region thin film layer comprises a hole injection layer, a hole transport layer, and an electron blocking layer, the electron transport region thin film layer comprises a hole blocking layer, an electron transport layer, and an electron injection layer, and the electron transport layer comprises the nitrogen-containing heterocyclic compound according to any one of claims 1 to 7.

Description

Nitrogen-containing heterocyclic compound and organic electroluminescent device comprising same Technical Field The invention relates to the technical field of semiconductor materials, in particular to a nitrogen-containing heterocyclic compound and an organic electroluminescent device containing the same. Background The organic electroluminescent device (OLED: organic Light Emission Diodes) technology can be used for manufacturing novel display products and novel illumination products, is hopeful to replace the existing liquid crystal display and fluorescent lamp illumination, and has wide application prospect. The organic electroluminescent device has a sandwich-like structure and comprises electrode material film layers and organic functional materials clamped between different electrode material film layers, wherein various different organic functional materials are mutually overlapped together according to purposes to jointly form the organic electroluminescent device. When voltage is applied to the electrodes at the two ends of the organic electroluminescent device as a current device and positive and negative charges in the organic layer functional material film layer are acted through an electric field, the positive and negative charges are further compounded in the luminescent layer, so that organic electroluminescent is generated. Currently, OLED display technology has been applied in the fields of smart phones, tablet computers, televisions, etc., but compared with the actual product application requirements, the performance of the organic electroluminescent device, such as luminous efficiency and service life, needs to be further improved. In order to realize the continuous improvement of the performance of the organic electroluminescent device, the organic photoelectric functional material is required to be continuously researched and innovated, and the organic photoelectric functional material with higher performance is created. The organic photoelectric functional materials applied to the organic electroluminescent devices can be divided into two main types in terms of application, namely charge injection transport materials and luminescent materials. Further, the charge injection transport material may be classified into an electron injection transport material, an electron blocking material, a hole injection transport material, and a hole blocking material, and as the charge transport material, it is required to have good carrier mobility, high glass transition temperature, and the like, and for an organic electroluminescent device, electrons are injected from a cathode and then transferred to a host material through an electron transport layer, and the holes are recombined in the host material, thereby generating excitons. Therefore, the injection capability and the transmission capability of the electron transmission layer are improved, the device driving voltage is reduced, and meanwhile, the high-efficiency electron-hole recombination efficiency is obtained. Therefore, the electron transport layer is very important, and it is required to have high electron injection capability, transport capability, and high durability of electrons. The heat resistance and film stability of the material are also important for the lifetime of the device, and a material having low heat resistance is easily decomposed not only at the time of material vapor deposition but also at the time of device operation by heat generated by the device, thereby causing material deterioration. Under the condition of poor phase stability of the material film, the material also generates film crystallization in a short time, so that the organic film layer is directly separated, and the device is deteriorated. Therefore, the materials used are required to have high heat resistance and good film stability. Along with the requirement of improving the performance of the organic electroluminescent device, the requirement on the material performance is also increasing, and not only is the material stability required, but also the material stability is required to reach good efficiency and service life under low driving voltage. However, the existing electron transport materials have insufficient heat resistance stability, and meanwhile, the electron tolerance of the materials has defects, so that the materials are separated or decomposed in a phase state when the device works, and the service life of the device is short. Disclosure of Invention Aiming at the problems in the prior art, the invention provides a nitrogen-containing heterocyclic compound and an organic electroluminescent device containing the same, and the compound has excellent electron injection and transmission capability, is applied to the organic electroluminescent device, and can effectively reduce the working voltage of the device and prolong the service life of the device. The invention provides a compound with a nitrogen-containing heterocyclic structure, w