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CN-117088899-B - Heterocyclic compound and organic electroluminescent device thereof

CN117088899BCN 117088899 BCN117088899 BCN 117088899BCN-117088899-B

Abstract

The invention provides a heterocyclic compound and an organic electroluminescent device thereof, and particularly relates to the technical field of organic electroluminescent materials. The heterocyclic compound provided by the invention has proper HOMO and LUMO energy levels, can be well matched with adjacent functional layers, can balance the hole and electron distribution in the organic electroluminescent device, improves the recombination probability of excitons, and realizes the maximum recombination of carriers, and in addition, the heterocyclic compound provided by the invention also has higher triplet state energy levels, good film forming property and thermal stability. When the heterocyclic compound provided by the invention is applied to the organic electroluminescent device as a main material of a luminescent layer, the luminescent efficiency of the device can be effectively improved, the service life of the device can be prolonged, and the overall performance of the device can be obviously improved.

Inventors

  • GUO JIANHUA
  • DU MINGZHU
  • SUN JING
  • SUN YUE

Assignees

  • 长春海谱润斯科技股份有限公司

Dates

Publication Date
20260508
Application Date
20230829

Claims (7)

  1. 1. A heterocyclic compound, characterized in that the heterocyclic compound is represented by a structure represented by formula I-1 or formula I-2: at least one of Ar 1 、Ar 2 is selected from any one of the following groups derived from formula II-1 or formula II-2: The a 1 is selected from 0,1, 2 or 3, the a 2 is selected from 0,1, 2,3, 4 or 5, the a 3 is selected from 0,1, 2,3, 4, 5,6 or 7, the a 4 is independently selected from 0,1, 2,3 or 4, the a 5 is selected from 0,1, 2,3, 4, 5 or 6, and when two or more R 2 are present, two or more R 2 are the same or different from each other; R 2 is selected from hydrogen, deuterium, tritium, cyano, halogen, or one or a combination of substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; when Ar 1 or Ar 2 is not formula II-1 or II-2, the compound is selected from any one of the following groups: The b 1 is selected from 0, 1,2,3, 4 or 5, the b 2 is selected from 0, 1,2,3 or 4, the b 3 is selected from 0, 1,2,3, 4, 5, 6 or 7, the b 4 is selected from 0, 1,2,3, 4, 5, 6, 7, 8 or 9, and when two or more R 3 are present, two or more R 3 are the same or different from each other; R 3 is the same or different selected from hydrogen, deuterium, tritium, cyano, fluorine, or one or a combination of substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutyl, cyclopentane, cyclohexane, adamantane, norbornane, phenyl; R d 、R e is independently selected from one or a combination of substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, biphenyl, terphenyl and naphthyl; The Z is selected from C (R 1 ) or N identically or differently, and at most one is selected from N, the R 1 is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C6 alkyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyltert-butylsilyl, substituted or unsubstituted phenyl, or two adjacent R 1 are connected to form a substituted or unsubstituted benzene ring; The ring A is selected from any one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl and substituted or unsubstituted pyridyl; The L 1 、L 2 is selected from a single bond or any one of the following groups: The c 1 is selected from 0, 1,2, 3 or 4, the c 2 is selected from 0, 1,2 or 3, when two or more R 4 are present, two or more R 4 are the same or different from each other; R 4 is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen and substituted or unsubstituted C1-C6 alkyl; r j 、R k is independently selected from substituted or unsubstituted C1-C6 alkyl; When Ar 1 or Ar 2 is not a group of formula II-1 or II-2, the L 1 or L 2 attached thereto is not ; The substituent represented by the substituent in the "substituted or unsubstituted" includes deuterium, tritium, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, propyl and butyl.
  2. 2. The heterocyclic compound according to claim 1, wherein at least one of Ar 1 、Ar 2 is selected from any one of the following groups derived from formula II-1 or formula II-2: the R 2 are identically or differently selected from hydrogen, deuterium, tritium.
  3. 3. The heterocyclic compound according to claim 1, wherein when Ar 1 or Ar 2 is not formula II-1 or formula II-2, it is selected from any one of the following groups: R 3 is the same or different and is selected from hydrogen, deuterium, tritium, or one or a combination of substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl and phenyl.
  4. 4. The heterocyclic compound according to claim 1, wherein L 1 、L 2 is selected from a single bond or any one of the following groups: the R 4 are identically or differently selected from one of hydrogen, deuterium, tritium or a combination thereof.
  5. 5. The heterocyclic compound according to claim 1, wherein the ring a is selected from any one of a substituted or unsubstituted phenyl group and a substituted or unsubstituted naphthyl group.
  6. 6. A heterocyclic compound, characterized in that the heterocyclic compound is selected from any one of the following compounds: 。
  7. 7. an organic electroluminescent device, characterized in that the organic layer comprises a light-emitting layer comprising at least one of the heterocyclic compounds according to any one of claims 1 to 6.

Description

Heterocyclic compound and organic electroluminescent device thereof Technical Field The invention relates to the technical field of organic electroluminescent materials, in particular to a heterocyclic compound and an organic electroluminescent device thereof. Background An Organic Light-Emitting Diode (OLED) is a novel flat panel display technology with the most development potential in recent years, and has the advantages of low driving voltage, high efficiency, high brightness, good flexibility, wide viewing angle, fast response speed, high resolution, light weight, low cost, wide material selection range and the like, so that the Organic Light-Emitting Diode has wide application prospect in the display and illumination fields, and is deeply valued by the scientific circles and the industry in recent years. The organic electroluminescent device is a carrier dual injection type device that converts electric energy into light energy. The organic electroluminescent device is generally in a sandwich structure, that is, an organic functional layer is sandwiched between an anode and a cathode at both sides of the device, and the organic layer generally includes a hole transport region, an electron transport region, a light emitting layer, and the like. The electron transport region can be divided into an electron injection layer, an electron transport layer and a hole blocking layer, and the light-emitting layer is divided into a host material and a guest material by adopting a host-guest doping mode. The light-emitting principle is that under the action of the externally applied electric field, the hole generated by the anode material and the electron generated by the cathode material are respectively injected into the OLED device, the hole and the electron are combined in the light-emitting layer to generate excitons, the molecules in the excited state are unstable, and the molecules return to the ground state in a radiation transition mode, so that energy is released in a light energy mode in the transition process to generate an electroluminescent phenomenon. The luminescent layer is used as the core part of the organic electroluminescent device, the use of the luminescent layer material plays a decisive role in the luminous efficiency of the device, and the luminescent layer material at present has the problems of mismatching of the energy level of a main material and an adjacent functional layer, mismatching of the triplet energy level of a main guest material and the like, which can lead to unbalanced migration of electrons and holes in the luminescent layer, reduce the recombination probability of excitons and further influence the luminous efficiency of the device. And the material technology and professional barriers of the luminescent layer material are high, so that the luminescent layer material is mainly monopolized by foreign markets. Therefore, in order to continuously improve the performance of the organic electroluminescent device, development of a main material of the luminescent layer with excellent performance is needed to reduce the driving voltage of the device, improve the luminous efficiency of the device, and prolong the service life of the device. Disclosure of Invention Aiming at the problems in the prior art, the invention provides a heterocyclic compound and an organic electroluminescent device thereof. Specifically, the technical scheme of the invention is as follows: the invention provides a heterocyclic compound, which is represented by a structure shown in a formula I-1 or a formula I-2: At least one of Ar 1、Ar2 is selected from a group shown in a formula II-1 or a formula II-2, and the rest is selected from one or a combination of deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroaromatic ring condensed ring groups: the Y 1、Y2 is independently selected from O or S; the ring B and the ring C are independently selected from any one of the following groups: Said x being identically or differently selected from C (R 2) or N, and at most one of said x being selected from N; The R 2 is the same or different and is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring condensed ring group, substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroaromatic ring condensed ring group, or two adjace