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CN-115498132-B - Organic electroluminescent device

CN115498132BCN 115498132 BCN115498132 BCN 115498132BCN-115498132-B

Abstract

The invention relates to the technical field of organic electroluminescence, in particular to an organic electroluminescent device. The invention applies the first compound shown in the formula (I) and the second compound shown in the formula (II) to the organic layer of the device at the same time, so that the energy level matching degree between the functional layers is high, the interface transmission performance between the layers is good, the charge transmission performance is good, the thermal stability and the chemical stability are good, and the organic light-emitting device with low driving voltage, high light-emitting efficiency and long service life is further provided.

Inventors

  • DONG XIUQIN
  • ZHOU WENTING
  • GUO JIANHUA

Assignees

  • 长春海谱润斯科技股份有限公司

Dates

Publication Date
20260512
Application Date
20220930

Claims (9)

  1. 1. An organic electroluminescent device comprising an anode, a cathode, and an organic layer between the anode and the cathode, the organic layer comprising a hole transport region, a light emitting layer, and an electron transport region, wherein the hole transport region comprises a first compound represented by formula (I) and a second compound represented by formula (II): wherein, L 1 、L 5 、L 6 is independently selected from a single bond or one of the structures shown as follows: Wherein each occurrence of said a 11 is identically or differently selected from 0, 1,2, 3, or 4, each occurrence of said b 11 is identically or differently selected from 0, 1,2, or 3; the R 13 groups are selected, identically or differently, from each occurrence, from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl; The L 2 、L 3 is independently selected from a single bond or one of the structures shown below: Wherein each occurrence of said a 12 is identically or differently selected from 0, 1,2, 3, or 4, each occurrence of said b 12 is identically or differently selected from 0, 1,2, or 3; each occurrence of R 16 is selected from the group consisting of a hydrogen atom, a deuterium atom, a methyl group, a deuterated methyl group, an ethyl group, a n-propyl group, an isopropyl group, a deuterated isopropyl group, a n-butyl group, a tert-butyl group, a deuterated tert-butyl group; The a 1 is selected, identically or differently, from 0,1, 2, 3 or 4 at each occurrence, the b 1 is selected from 0,1, 2 or 3; The R 1 is selected from one of hydrogen atom, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C10 cycloalkyl and substituted or unsubstituted C6-C14 aryl, wherein the 'substituted or unsubstituted' in R 1 represents that the R 1 is not substituted or is substituted by more than one substituent selected from the group consisting of deuterium atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl; The R 2 is selected from one of hydrogen atom, deuterium atom, tritium atom and substituted or unsubstituted C1-C6 alkyl, wherein the 'substituted or unsubstituted' in R 2 represents that the R 2 is not substituted or is substituted by more than one substituent selected from the group consisting of deuterium atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl; At least one of Ar 1 ～Ar 4 is selected from one of C6-C14 aryl groups substituted with deuterium atoms, the rest is independently selected from one of substituted or unsubstituted C6-C14 aryl groups, the "substituted or unsubstituted" in Ar 1 ～Ar 4 means that the substituent is not substituted or is substituted with more than one substituent selected from the group consisting of deuterium atoms, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexenyl, cycloheptene, adamantane, norbornane and phenyl; The L 4 is selected from one of the following structures: Wherein each occurrence of said a 21 is selected from the group consisting of 1,2, 3, and 4 identically or differently, each occurrence of said b 21 is selected from the group consisting of 1,2, and 3 identically or differently, each occurrence of said c 21 is selected from the group consisting of 1 and 2 identically or differently; r 21 、R 22 is independently selected from hydrogen atom, deuterium atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl; The R 23 groups are selected, identically or differently, from each occurrence, from hydrogen atoms, deuterium atoms, methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, and at least one R 23 group is selected from deuterium atoms; The R 3 is selected from one of substituted or unsubstituted C6-C14 aryl, the substituted or unsubstituted R 3 is unsubstituted or substituted by more than one substituent selected from the group consisting of deuterium atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexenyl, cycloheptene, adamantane and norbornane; The c 1 is selected from 0,1, 2,3 or 4, and the d 1 is selected from 0,1, 2 or 3; The R 4 is selected from hydrogen atom, deuterium atom, tritium atom, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C14 aryl, or adjacent two R 4 are connected to form a substituted or unsubstituted benzene ring, wherein the "substituted or unsubstituted" in R 4 represents that the R is not substituted or is substituted by more than one substituent selected from the group consisting of deuterium atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl; Ar 5 、Ar 6 is independently selected from one of substituted or unsubstituted C6-C14 aryl groups, ar 5 、Ar 6 is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropane, cyclobutyl, cyclopentane, cyclohexenyl, cycloheptane, cyclopentenyl, cyclohexenyl, cycloheptenyl, adamantyl, norbornane and phenyl.
  2. 2. The organic electroluminescent device of claim 1, wherein L 1 、L 5 、L 6 is independently selected from a single bond or one of the following structures: Each occurrence of said R 13 is identically selected from hydrogen atoms; The L 2 、L 3 is independently selected from a single bond or one of the structures shown below: each occurrence of said R 16 is identically selected from hydrogen atoms.
  3. 3. The organic electroluminescent device according to claim 1, wherein each occurrence of R 1 is the same or different and is selected from the group consisting of hydrogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, norbornyl substituted or unsubstituted with methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, adamantyl substituted or unsubstituted with methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropylalkyl substituted or unsubstituted with methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclobutylalkyl substituted or unsubstituted with methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopentylalkyl substituted or unsubstituted with methyl, ethyl, n-propyl, n-butyl, tert-butyl, cyclohexylalkyl substituted or unsubstituted with methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl substituted or unsubstituted with one of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl; The R 2 is selected from one of hydrogen atom, deuterium atom, tritium atom, methyl, ethyl, n-propyl, isopropyl, n-butyl and tert-butyl.
  4. 4. The organic electroluminescent device according to claim 1, wherein at least one of the Ar 1 ～Ar 4 is represented by one selected from a phenyl group substituted with a deuterium atom, a naphthyl group substituted with a deuterium atom, an anthryl group substituted with a deuterium atom, a phenanthryl group substituted with a deuterium atom, a 9, 9-dimethylfluorenyl group substituted with a deuterium atom, a 9, 9-diphenylfluorenyl group substituted with a deuterium atom, a 9-methyl-9-phenylfluorenyl group substituted with a deuterium atom, a biphenyl group substituted with a deuterium atom, and the others are independently represented by one selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, and a substituted or unsubstituted fluorenyl group.
  5. 5. The organic electroluminescent device of claim 1, wherein L 4 is selected from one of the following structures: R 21 、R 22 is independently selected from one of methyl, ethyl, n-propyl, isopropyl, n-butyl and tert-butyl; The R 23 groups are each independently selected from hydrogen atoms, one of deuterium atoms, and at least one R 23 group is selected from deuterium atoms.
  6. 6. The organic electroluminescent device of claim 1, wherein R 3 is selected from one of the following structures: Wherein a 31 is selected, identically or differently, for each occurrence, from 0, 1, 2,3,4, or 5, b 31 is selected, identically or differently, for each occurrence, from 0, 1, 2,3,4, 5,6, or 7, and c 31 is selected, identically or differently, for each occurrence, from 0, 1, 2,3,4, 5,6, 7, 8, or 9; R 31 is selected from one of hydrogen atom, deuterium atom, methyl, ethyl, n-propyl, isopropyl, n-butyl and tert-butyl identically or differently at each occurrence.
  7. 7. The organic electroluminescent device of claim 1, wherein Ar 5 、Ar 6 is selected from one of the following structures: Wherein the a 41 is selected from 0, 1,2, 3, 4, or 5 identically or differently for each occurrence, the b 41 is selected from 0, 1,2, 3, 4,5, 6, or 7 identically or differently for each occurrence, the c 41 is selected from 0, 1,2, 3, 4,5, 6, 7, 8, or 9 identically or differently for each occurrence, the d 41 is selected from 0, 1,2, 3, or 4 identically or differently for each occurrence, and the e 41 is selected from 0, 1,2, or 3 identically or differently for each occurrence; R 41 is selected from one of hydrogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, tertiary butyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl and phenyl, which are the same or different at each occurrence; And R 43 ～R 45 is independently selected from one of methyl, ethyl and phenyl.
  8. 8. The organic electroluminescent device of claim 1, wherein the first compound is selected from one of the following structures:
  9. 9. the organic electroluminescent device of claim 1, wherein the second compound is selected from one of the following structures:

Description

Organic electroluminescent device Technical Field The invention belongs to the technical field of organic electroluminescence, and particularly relates to an organic electroluminescent device. Background An Organic Light-Emitting Diode (OLED) is a current-type Organic Light-Emitting device that emits Light by carrier injection and recombination. As a self-luminous element, the light-emitting element has the characteristics of excellent contrast, wide visual angle, high response speed, low energy consumption, high efficiency, good flexibility and the like, and is widely applied to the fields of illumination and display, simultaneously meets the new requirements of consumers on display technology, and has wide development prospect. The classical OLED device is in a "sandwich" structure, with a luminescent layer sandwiched between two electrodes, the cathode and the anode, wherein the luminescent layer contains luminescent substances. The organic light emitting phenomenon is one of examples of converting current into visible light through an internal process of a specific organic molecule. When voltage is applied between the two electrodes, electrons and holes are injected from the cathode and the anode respectively, excitons are formed by recombination of the light-emitting layers, the light-emitting substances in the light-emitting layers of the device are activated by the excitons, electrons in the molecules of the light-emitting substances are transited from a ground state to an excited state, the electrons in the excited state are extremely unstable, the electrons are transited to a stable ground state, and energy is released in a light form in the transition process, so that the light emission of the device is realized. In order to improve the performance of the OLED, such as luminous efficiency, color purity and the like, more other organic functional layers are additionally arranged between the anode and the luminous layer and between the cathode and the luminous layer. Such as a hole injection layer, a hole transport layer, etc., between the anode and the light-emitting layer, an electron injection layer, an electron transport layer, etc., between the cathode and the light-emitting layer. In view of the disadvantages of high driving voltage, poor light-emitting performance and short service life caused by the problem of energy level matching in the conventional devices, development of an organic electroluminescent device with good energy level matching and excellent light-emitting performance is needed. Disclosure of Invention In order to solve the technical problems, the invention provides an organic electroluminescent device with high energy level matching degree, good luminous performance and long service life of various organic functional layers, which comprises an anode, a cathode and an organic layer between the anode and the cathode, wherein the organic layer comprises a hole transport region, a luminous layer and an electron transport region, and the organic layer contains a first compound shown as a formula (I) and a second compound shown as a formula (II): Wherein, L 1～L3、L5、L6 is independently selected from one of single bond, substituted or unsubstituted arylene of C6-C30; The a 1 is selected from 0, 1,2,3 or 4 identically or differently for each occurrence, the b 1 is selected from 0, 1,2 or 3; r 1 is selected from one of hydrogen atoms, substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C10 cycloalkyl groups and substituted or unsubstituted C6-C30 aryl groups, which are the same or different at each occurrence; R 2 is selected from one of hydrogen atom, deuterium atom, tritium atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C10 cycloalkyl and substituted or unsubstituted C6-C30 aryl, which are the same or different at each occurrence; Ar 1～Ar4 is independently selected from one of substituted or unsubstituted aryl groups of C6-C30, ar 1 is connected with Ar 2 to form a ring, or Ar 3 is connected with Ar 4 to form a ring; L 4 is selected from one of C6-C30 arylene groups substituted by deuterium atoms or tritium atoms; r 3 is selected from one of substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl; The c 1 is selected from 0,1, 2,3 or 4, and the d 1 is selected from 0,1, 2 or 3; R 4 is selected from one of hydrogen atom, deuterium atom, tritium atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, or two adjacent R 4 are connected to form substituted or unsubstituted saturated or unsaturated C3-C6 carbocycle; ar 5、Ar6 is independently selected from one of substituted or unsubstituted aryl groups of C6-C30; Provided that at least one of said Ar 1～Ar4、R2、L2、L3 contains more than one deuterium or tritium atom. The beneficial effects are that: The invention applies the first compound shown in the formula (I