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CN-122010855-A - Nitrogen-containing heterocyclic compound and organic electroluminescent device thereof

CN122010855ACN 122010855 ACN122010855 ACN 122010855ACN-122010855-A

Abstract

The invention belongs to the technical field of organic photoelectric materials, and particularly relates to a nitrogen-containing heterocyclic compound and an organic electroluminescent device thereof. The nitrogen-containing heterocyclic compound provided by the invention has good electron migration capability, proper HOMO energy level and LUMO energy level, can improve the electron transmission efficiency when being applied to an electron transmission region, can be well matched with an adjacent organic functional layer in energy level, is favorable for generating excitons in a luminescent layer, thereby improving the luminous efficiency, service life and driving voltage of a device, and has good thermal stability and chemical stability, is not easy to decompose and age under the working environment of high temperature and corrosive gas, has good film forming property, and can further improve the service life and stability of the device.

Inventors

  • DU MINGZHU
  • MIAO YUHE
  • LIANG ZHICONG

Assignees

  • 长春海谱润斯科技股份有限公司

Dates

Publication Date
20260512
Application Date
20260213

Claims (10)

  1. 1. The nitrogen-containing heterocyclic compound is characterized by having a structure shown in a formula (I): Wherein X, Y is selected from CR or N identically or differently for each occurrence, and at least one X is selected from N, and at least one Y is selected from N, and R is selected from one of a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted heteroaryl group in C3-C30, a substituted or unsubstituted C3-C12 aliphatic ring, and a monovalent group formed by fusing a C6-C30 aromatic ring, identically or differently for each occurrence; The R 2 、R 3 is independently selected from one of a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, or the R 2 、R 4 is independently selected from one of a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, or the R 3 、R 4 is independently selected from one of a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, or the R 1 、R 2 is independently selected from one of a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, or a substituted or unsubstituted C3-C12 cycloalkyl group: Each occurrence of said a 11 is identically or differently selected from 0, 1,2, 3,4 or 5; said b 11 is selected identically or differently from 0, 1,2, 3,4, 5,6 or 7 for each occurrence; said c 11 is selected identically or differently at each occurrence from 0, 1,2, 3,4, 5,6, 7, 8 or 9; the d 11 is selected from 0, 1,2, 3,4, 5,6, 7, 8,9, 10, or 11 on each occurrence, the e 11 is selected from 0, 1,2, or 3 on each occurrence, the f 11 is selected from 0, 1,2, 3, or 4 on each occurrence, the g 11 is selected from 0, 1, or 2 on each occurrence, the h 11 is selected from 0, 1,2, 3,4, 5, or 6 on each occurrence, the i 11 is selected from 0, 1,2, 3,4, 5,6, 7, or 8 on each occurrence, the j 11 is selected from 0, 1,2, 3,4, 5,6, 7, 8,9, or 10 on each occurrence, and the k 11 is selected from 0, 1,2, 3,4, 5,6, 7, 9, or 10 on each occurrence; R 11 is selected from one of hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C12 aliphatic ring and C6-C30 aromatic ring fused monovalent group or two adjacent R 11 can be connected to form a ring; R 12 is selected from one of hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano, substituted or unsubstituted C1-C12 alkyl and substituted or unsubstituted C3-C12 cycloalkyl, which are the same or different at each occurrence; X 1 is selected from O, S or CR 13 R 14 , and X 2 is selected from O, S or NR 15 ; R 13 、R 14 、R 15 、R 16 is independently selected from one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and monovalent groups formed by fusing a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; Ar 1 、Ar 2 、Ar 3 、Ar 4 is independently selected from one of substituted or unsubstituted aryl of C6-C30, substituted or unsubstituted heteroaryl of C3-C30, substituted or unsubstituted aliphatic ring of C3-C12 and monovalent group formed by fusing aromatic ring of C6-C30, wherein each occurrence of the substituent is the same or different selected from one of deuterium atom, tritium atom, halogen atom, substituted or unsubstituted alkyl of C1-C30, substituted or unsubstituted cycloalkyl of C3-C30, substituted or unsubstituted aryl of C6-C30, substituted or unsubstituted heteroaryl of C2-C30 and monovalent group formed by fusing aliphatic ring of C3-C12 and aromatic ring of C6-C30; The L 1 、L 2 、L 3 、L 4 、L 11 is independently selected from one of single bond, substituted or unsubstituted arylene of C6-C30, substituted or unsubstituted heteroarylene of C2-C30, bivalent group formed by fusing substituted or unsubstituted aliphatic ring of C3-C12 and aromatic ring of C6-C30, and each occurrence of the substituent is the same or different from one of deuterium atom, tritium atom, halogen atom, substituted or unsubstituted alkyl of C1-C30, substituted or unsubstituted cycloalkyl of C3-C30, substituted or unsubstituted aryl of C6-C30, substituted or unsubstituted heteroaryl of C2-C30, and monovalent group formed by fusing substituted or unsubstituted aliphatic ring of C3-C12 and aromatic ring of C6-C30.
  2. 2. The nitrogen-containing heterocyclic compound according to claim 1, wherein at least one X is selected from N, or at least two X are selected from N, or three X are selected from N; at least one Y is selected from N, or at least two Y are selected from N, or three Y are selected from N.
  3. 3. The nitrogen-containing heterocyclic compound according to claim 1, wherein the nitrogen-containing heterocyclic compound has a structure represented by one of the formulae (II-a) to (II-E): 。
  4. 4. The nitrogen-containing heterocyclic compound according to claim 1, wherein Ar 1 、Ar 2 、Ar 3 、Ar 4 is independently selected from one of the following groups: Each occurrence of said a 21 is identically or differently selected from 0, 1,2, 3,4 or 5; said b 21 is selected identically or differently from 0, 1,2, 3,4, 5,6 or 7 for each occurrence; said c 21 is selected identically or differently at each occurrence from 0, 1,2, 3,4, 5,6, 7, 8 or 9; the d 21 is selected from 0, 1,2, 3,4, 5,6, 7, 8,9, 10, or 11 on each occurrence, the e 21 is selected from 0, 1,2, or 3 on each occurrence, the f 21 is selected from 0, 1,2, 3, or 4 on each occurrence, the g 21 is selected from 0, 1, or 2 on each occurrence, the h 21 is selected from 0, 1,2, 3,4, 5, or 6 on each occurrence, the i 21 is selected from 0, 1,2, 3,4, 5,6, 7, or 8 on each occurrence, the j 21 is selected from 0, 1,2, 3,4, 5,6, 7, 8,9, or 10 on each occurrence, and the k 21 is selected from 0, 1,2, 3,4, 5,6, 7, 9, or 10 on each occurrence; r 21 is selected from one of hydrogen atom, deuterium atom, tritium atom, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C12 aliphatic ring and C6-C30 aromatic ring fused monovalent group, or two adjacent R 21 can be connected to form a ring; R 22 is selected from one of hydrogen atom, deuterium atom, tritium atom, halogen atom, substituted or unsubstituted C1-C12 alkyl and substituted or unsubstituted C3-C12 cycloalkyl, which are the same or different at each occurrence; X 3 is selected from O, S, CR 23 R 24 or NR 25 , and X 4 is selected from O, S or NR 25 ; R 23 、R 24 、R 25 、R 26 is independently selected from one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and a monovalent group formed by fusing a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring, or R 23 and R 24 are connected to form a ring.
  5. 5. The nitrogen-containing heterocyclic compound according to claim 1, wherein L 1 、L 2 、L 3 、L 4 、L 11 is independently selected from a single bond, one of the following groups: Wherein X 5 is selected from O or S; The a 101 is selected from 0,1, 2,3, or 4 on each occurrence identically or differently, the b 101 is selected from 0,1, 2,3,4, 5, or 6 on each occurrence identically or differently, the c 101 is selected from 0,1, 2,3,4, 5, 6, 7, or 8 on each occurrence identically or differently, the d 101 is selected from 0,1, or 2 on each occurrence identically or differently, the e 101 is selected from 0,1, 2,3,4, 5, 6, 7, 8, 9, or 10 on each occurrence identically or differently, the f 101 is selected from 0,1, 2, or 3 on each occurrence identically or differently, the g 101 is selected from 0,1, 2,3,4, or 5 on each occurrence identically or differently; R 101 is one of hydrogen atom, deuterium atom, tritium atom, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C12 aliphatic ring and C6-C30 aromatic ring fused monovalent group; R 102 is selected from one of hydrogen atom, deuterium atom, tritium atom, halogen atom, substituted or unsubstituted C1-C12 alkyl and substituted or unsubstituted C3-C12 cycloalkyl, which are the same or different at each occurrence.
  6. 6. The nitrogen-containing heterocyclic compound according to claim 1, wherein the nitrogen-containing heterocyclic compound is selected from one of the following compounds: 。
  7. 7. an organic electroluminescent device comprising a cathode, an anode, and an organic layer, wherein the organic layer is disposed between the cathode and the anode, and the organic layer comprises a hole transport region, a light emitting layer, and an electron transport region, wherein the organic layer comprises the nitrogen-containing heterocyclic compound according to any one of claims 1 to 6.
  8. 8. The organic electroluminescent device according to claim 7, wherein the electron transporting region contains the nitrogen-containing heterocyclic compound according to any one of claims 1 to 6.
  9. 9. The organic electroluminescent device according to claim 8, wherein the electron transport region comprises an electron transport layer, wherein the electron transport layer comprises the nitrogen-containing heterocyclic compound according to any one of claims 1 to 6.
  10. 10. The organic electroluminescent device according to claim 8, wherein the electron transport region comprises a hole blocking layer, wherein the hole blocking layer comprises the nitrogen-containing heterocyclic compound according to any one of claims 1 to 6.

Description

Nitrogen-containing heterocyclic compound and organic electroluminescent device thereof Technical Field The invention belongs to the technical field of organic photoelectric materials, and particularly relates to a nitrogen-containing heterocyclic compound and an organic electroluminescent device thereof. Background Organic electroluminescent devices (OLEDs) have advantages of self-luminescence, light and thin body, wide viewing angle, rapid response, wide use temperature range, low power consumption, high efficiency, high color purity, high definition, flexible display, etc., and are considered as one of display and illumination technologies with the most development prospects. The OLED adopts a multi-layer film structure, and comprises an anode, a cathode and a light-emitting layer, wherein the light-emitting layer is positioned between the anode and the cathode, and also comprises various organic functional layers in a hole transmission area between the anode and the light-emitting layer and various organic functional layers in an electron transmission area between the cathode and the light-emitting layer. After voltage is applied, holes injected by the anode and electrons injected by the cathode pass through each organic functional layer to reach the light-emitting layer, excitons are formed by recombination in the light-emitting layer, and energy is released in a photon form by the excitons through a radiation transition process, so that visible light is generated. It follows that the OLED device is through the synergistic effect between the various organic functional layers to achieve efficient electroluminescence. Among them, the organic functional layer in the electron transport region includes an electron injection layer, an electron transport layer, a hole blocking layer, etc., plays a role of injecting and transporting electrons, and also plays a role of promoting the generation of excitons in the light emitting layer, which is required to have good electron transport ability, and proper HOMO and LUMO levels. In order to further improve the driving voltage, luminous efficiency, service life and other performances of the OLED device, development of an electron transport material with more excellent performance is still required. Disclosure of Invention In order to solve the technical problems, the invention provides a nitrogen-containing heterocyclic compound, which has a structure shown in a formula (I): Wherein X, Y is selected from CR or N identically or differently for each occurrence, and at least one X is selected from N, and at least one Y is selected from N, and R is selected from one of a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted heteroaryl group in C3-C30, a substituted or unsubstituted C3-C12 aliphatic ring, and a monovalent group formed by fusing a C6-C30 aromatic ring, identically or differently for each occurrence; The R 2、R3 is independently selected from one of a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, or the R 2、R4 is independently selected from one of a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, or the R 3、R4 is independently selected from one of a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, or the R 1、R2 is independently selected from one of a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, or a substituted or unsubstituted C3-C12 cycloalkyl group: Each occurrence of said a 11 is identically or differently selected from 0, 1,2, 3,4 or 5; said b 11 is selected identically or differently from 0, 1,2, 3,4, 5,6 or 7 for each occurrence; said c 11 is selected identically or differently at each occurrence from 0, 1,2, 3,4, 5,6, 7, 8 or 9; the d 11 is selected from 0, 1,2, 3,4, 5,6, 7, 8,9, 10, or 11 on each occurrence, the e 11 is selected from 0, 1,2, or 3 on each occurrence, the f 11 is selected from 0, 1,2, 3, or 4 on each occurrence, the g 11 is selected from 0, 1, or 2 on each occurrence, the h 11 is selected from 0, 1,2, 3,4, 5, or 6 on each occurrence, the i 11 is selected from 0, 1,2, 3,4, 5,6, 7, or 8 on each occurrence, the j 11 is selected from 0, 1,2, 3,4, 5,6, 7, 8,9, or 10 on each occurrence, and the k 11 is selected from 0, 1,2, 3,4, 5,6, 7, 9, or 10 on each occurrence; R 11 is selected from one of hydrogen atom, deuterium atom, tritium atom, halogen atom,