CN114512618A - Organic light emitting device - Google Patents

Organic light emitting device Download PDF

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CN114512618A
CN114512618A CN202011290380.9A CN202011290380A CN114512618A CN 114512618 A CN114512618 A CN 114512618A CN 202011290380 A CN202011290380 A CN 202011290380A CN 114512618 A CN114512618 A CN 114512618A
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王志鹏
张艳
高文正
曾礼昌
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Beijing Eternal Material Technology Co Ltd
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
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    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring

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Abstract

The invention relates to an organic light-emitting device, which comprises a first electrode, a second electrode and an organic layer positioned between the first electrode and the second electrode, wherein the organic layer comprises an electron blocking layer and a light-emitting layer; the electron blocking layer comprises a compound with a structure shown in a general formula (A), the light-emitting layer comprises a compound shown in a general formula (3) as a guest material, and the electron blocking layer material with the structure shown in the general formula (A) is specifically matched with the guest material shown in the general formula (3) in the light-emitting device, so that the performance and the stability of the device can be improved.
Figure DDA0002783638310000011

Description

Organic light emitting device
Technical Field
The present invention relates to an organic light emitting device, and more particularly, to an organic light emitting device having a low driving voltage and a high light emitting efficiency.
Background
The organic electroluminescent device (OLED) of the organic electroluminescent material can be used in the fields of solid-state light-emitting full-color display, solid-state white light illumination and the like. An organic light-emitting device generally includes a light-emitting layer and a pair of opposed electrodes sandwiching the light-emitting layer. When an electric field is applied between the electrodes, electrons are injected from the cathode side and holes are injected from the anode side, the electrons are recombined with the holes in the light-emitting layer to form an excited state, and energy is released as light when the excited state returns to the ground state. With the continuous advance of the OLED technology in the two fields of illumination and display, people pay more attention to the research on the core materials of the OLED technology, and an organic electroluminescent device with good efficiency and long service life is generally the result of the optimized matching of the device structure and various organic materials, which provides great opportunities and challenges for chemists to design and develop functional materials with various structures. Common functionalized organic materials are: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, and light emitting host materials and light emitting objects (dyes), and the like. In order to prepare a light emitting device with better performance, the industry is continuously working on developing new organic electroluminescent materials to further improve the luminous efficiency and the lifetime of the device.
It is known that a blue light emitting material having excellent efficiency has been the focus of development in the industry. Currently, in organic light emitting devices (organic light emitting diodes (OLEDs)), commercial blue light emitting devices are mainly fluorescent materials due to the high emission level of blue light. While new light-emitting guest materials are continuously developed, the blue light-emitting performance is improved by optimizing the device structure, but whether carrier transmission balance in the light-emitting layer greatly affects the device performance.
It is known that by disposing an electron blocking layer adjacent to the light emitting layer, the transport speed of hole charges can be adjusted, carriers can be balanced, excitation of electrons and holes at the interface between the main body and the electron blocking layer can be avoided, and the recombination region of excitons in the main body can be increased, thereby improving the device performance. The present inventors have been working on developing organic functional materials, and have proposed various materials suitable for an electron blocking layer. Among them, chinese patent application CN110317139A discloses a compound having a triarylamine structure with the following specific structure as a hole transport layer and an electron blocking layer (please refer to corresponding patent documents for each symbol representing meaning).
Figure BDA0002783638290000011
However, the effect of these compounds in red and green phosphorescent light emitting devices described in chinese patent CN110317139A is very different from the light emitting system of blue light emitting devices, and the inventors of the present invention have studied and found that they do not show good effect in the conventional fluorescent light emitting devices, and thus are difficult to be used in blue fluorescent light emitting devices. Under the present circumstances, development of a blue fluorescent organic electroluminescent device having higher performance is urgently required.
Disclosure of Invention
In view of the above technical problems, the inventors of the present invention, after intensive research, have obtained the following findings: although the above-mentioned compound having a specific triarylamine structure hardly exhibits excellent performance in a fluorescent light-emitting device due to energy level matching, there is an exception that a very significant effect can be exhibited only when it is combined with a specific blue fluorescent guest material of the following general formula (3) (which may be referred to as a BN type guest material in the present invention). Based on such recognition, the present invention can provide a blue organic light emitting device having a lower driving voltage, as well as higher light emitting efficiency and lifetime.
Figure BDA0002783638290000021
A BN type guest material of the formula (3) wherein RB1～RB5Represents one or more substituents, ring C1～C4Represents an aryl or heteroaryl ring, it being noted that the relevant contents of this class of compounds are described in the document of patent application CN 107851724A.
Specifically, an organic light-emitting device of the present invention is characterized in that,
the organic electroluminescent device comprises a first electrode, a second electrode and an organic layer positioned between the first electrode and the second electrode, wherein the organic layer comprises an electron blocking layer and a light-emitting layer, the electron blocking layer comprises a compound with a structure shown in a following general formula (A), the light-emitting layer comprises a compound with a structure shown in a following general formula (3) as a guest material,
Figure BDA0002783638290000022
wherein X is selected from O, S, CR5R6、NR7Or SiR8R9；
Ring A represents C6～C30Aromatic ring of (A) or (C)3～C30The heteroaromatic ring of (a) is a ring,
l is selected from single bond, substituted or unsubstituted C6～C30Arylene or substituted or unsubstituted C3～C30A heteroarylene group;
L1selected from single bond, substituted or unsubstituted C6～C11Arylene or substituted or unsubstituted C3～C11A heteroarylene group;
Ar2selected from substituted or unsubstituted C6～C30Aryl or substituted or unsubstituted C3～C30Heteroaryl of (A), Ar2The ring A to which it is attached may be substituted by-O-, -S-, -CR-10R11-、-NR12-or-SiR13R14-linked to form a ring;
R1～R3each independently selected from hydrogen, substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C3～C30Heteroaryl group, C1～C30Alkyl radical, C1～C30Alkoxy radical, C7～C30Arylalkoxy group, C3～C30Cycloalkyl, C2～C30Alkenyl radical, C2～C30Alkynyl, C1～C30A combination of one or more of silane groups, carbonyl groups, and R1Ar can be connected into a ring;
m is an integer of 0-5, n is an integer of 0-7, p is an integer of 0-5, q is an integer of 0-5, and p + q is less than or equal to 5;
Ar1selected from substituted or unsubstituted C6～C30Aryl orSubstituted or unsubstituted C3～C23Heteroaryl of Ar1When having a substituent, the substituent is selected from the group consisting of halogen and C1～C30Alkyl radical, C3～C30Cycloalkyl radical, C2～C30Alkenyl radical, C1～C30Alkoxy or thioalkoxy, cyano, nitro, C1～C17Amino, carboxyl, aldehyde, ester, C6～C30Aryl radical, C3～C30A combination of one or more of heteroaryl groups,
r is as defined above5～R14Each independently selected from hydrogen and C1～C18Alkyl radical, C1～C18Alkoxy radical, C3～C30Cycloalkyl of (C)2～C18Alkenyl radical, C2～C18Alkynyl, halogen, cyano, substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C3～C30Heteroaryl, substituted or unsubstituted C6～C30Arylamino, substituted or unsubstituted C3～C30One or more of a heteroaromatic amine group,
when each of the above-mentioned substituted or unsubstituted groups has a substituent, the substituent is selected from the group consisting of halogen and C1～C30Alkyl radical, C3～C30Cycloalkyl radical, C2～C30Alkenyl radical, C1～C30Alkoxy or thioalkoxy, cyano, nitro, C1～C30Amino, carboxyl, aldehyde, ester, C6～C30Aryl radical, C3～C30A combination of one or more of heteroaryl groups;
Figure BDA0002783638290000031
wherein, ring C1～C4Represents an aryl or heteroaryl ring; rB1～RB5Represents hydrogen or one or more chemically reasonable substituents selected from halogen, C1～C30Alkyl radical, C3～C30Cycloalkyl radical, C2～C30Alkenyl radical, C1～C30Alkoxy group of (1), C6～C30Aryl radical, C3～C30Heteroaryl group, C12～C60Diarylamino, C6～C60Aryl heteroaryl amino, which can be connected with each other to form a ring, or can be connected with other groups beside to form a ring; x1、X2Represents N or O when X1、X2When is O, C1、C4And substituents thereof are absent.
Through the combination of the specific electron blocking layer material and the blue light guest dye, the blue light emitting device with lower excitation voltage and higher luminous efficiency is realized. When the electron blocking layer material with the structure shown in the general formula (a) is not matched with the object material with the structure type shown in the general formula (3) and is matched with other blue fluorescent objects to be used in a blue fluorescent device, compared with the prior art, almost no device efficiency improvement effect exists. The reason for realizing the above effect is not clear, and the energy levels between the two are presumed to be more matched, so that the injection capability of hole carriers is improved, the transmission balance of the carriers is improved, and the recombination area can be greatly increased, so that the driving voltage of the device can be reduced, the luminous efficiency is improved, and the service life of the device is prolonged.
Drawings
Fig. 1 is a schematic structural view of an organic electroluminescent device provided in embodiment 1 of the present invention.
Description of reference numerals:
1-anode, 2-hole injection layer, 3-hole transport layer, 4-electron blocking layer, 5-luminescent layer, 6-electron transport layer, 7-electron injection layer and 8-cathode.
Detailed Description
Description of the general description
In this specification, C representsa～CbThe expression (b) represents that the group has the number of carbon atoms of a to b, and generally the number of carbon atoms does not include the number of carbon atoms of the substituent unless otherwise specified. In the present invention,unless otherwise specified, the expressions of chemical elements generally include the concept of chemically identical isotopes, such as the expression "hydrogen" and also the concept of chemically identical "deuterium" and "tritium", and carbon (C) includes12C、13C, etc., will not be described in detail.
In the structural formulae disclosed in the present specification, the expression of the "-" underlined loop structure indicates that the linking site is located at an arbitrary position on the loop structure where the linking site can form a bond.
In the present specification, unless otherwise specified, both aryl and heteroaryl groups include monocyclic and fused rings. The monocyclic aryl group means that at least one phenyl group is contained in the molecule, and when at least two phenyl groups are contained in the molecule, the phenyl groups are independent of each other and are linked by a single bond, illustratively, a phenyl group, a biphenylyl group, a terphenylyl group, or the like; the fused ring aryl group means that at least two benzene rings are contained in the molecule, but the benzene rings are not independent of each other, but common ring sides are fused with each other, and exemplified by naphthyl, anthryl and the like; monocyclic heteroaryl means that the molecule contains at least one heteroaryl group, and when the molecule contains one heteroaryl group and other groups (e.g., aryl, heteroaryl, alkyl, etc.), the heteroaryl and other groups are independent of each other and are linked by a single bond, illustratively pyridine, furan, thiophene, etc.; fused ring heteroaryl refers to a fused ring of at least one phenyl group and at least one heteroaryl group, or, fused ring of at least two heteroaryl rings, illustratively quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, and the like
In the present specification, substituted or unsubstituted C6～C30Aryl is preferably C6～C20More preferably, the aryl group is a group selected from the group consisting of phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthrenyl, phenylphenanthracenyl, pyrenyl, perylenyl, anthrylenyl, tetracenyl, benzopyrenyl, biphenylyl, idophenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, trimeric indenyl, isotridecylindenyl, spirotrimeric indenyl, spiroisoindenylidene.Specifically, the biphenyl group is selected from 2-biphenyl, 3-biphenyl, and 4-biphenyl; terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes a 1-naphthyl group or a 2-naphthyl group; the anthracene group is selected from 1-anthracene group, 2-anthracene group and 9-anthracene group; the fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetracene group is selected from the group consisting of 1-tetracene, 2-tetracene, and 9-tetracene. Preferred examples of the aryl group in the present invention include phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl and derivatives thereof, anthryl, triphenylenyl, pyrenyl, perylenyl, perylene, and the like,
Figure BDA0002783638290000041
A group of the group consisting of a phenyl group and a tetracenyl group. The biphenyl group is selected from the group consisting of 2-biphenyl, 3-biphenyl, and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes a 1-naphthyl group or a 2-naphthyl group; the anthracene group is selected from the group consisting of 1-anthracene group, 2-anthracene group, and 9-anthracene group; the fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the fluorenyl derivative is selected from the group consisting of 9, 9 '-dimethylfluorene, 9' -spirobifluorene and benzofluorene; the pyrenyl group is selected from the group consisting of 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetracene group is selected from the group consisting of 1-tetracene, 2-tetracene, and 9-tetracene.
Specific examples of the arylene group in the present invention include divalent groups obtained by removing one hydrogen atom from the above-mentioned examples of the aryl group.
The heteroatom in the present invention is generally referred to as being selected from N, O, S, P, Si and Se, preferably from N, O, S.
In the present specification, substituted or unsubstituted C3～C30Heteroaryl is preferably C4～C20The heteroaryl group is more preferably a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, etc., and specific examples thereof include: furyl, thienyl, pyrrolyl, pyridyl, benzofuryl, benzothienyl, isobenzofuryl, isobenzothienyl, indolyl, isoindolyl, dibenzofuryl, dibenzothienyl, carbazolyl and derivatives thereof, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, phenothiazinyl, phenazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalimidazolyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthraoxazolyl, phenanthroizolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzpyridazinyl, Pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazananthracenyl, 2, 7-diazpyrenyl, 2, 3-diazpyrenyl, 1, 6-diazenyl, 1, 8-diazenyl, 4, 5, 9, 10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbazinyl, phenanthrolinyl, 1, 2, 3-triazolyl, 1, 2, 4-triazolyl, benzotriazolyl, 1, 2, 3-oxadiazolyl, 1, 2, 4-oxadiazolyl, 1, 2, 5-oxadiazolyl, 1, 2, 3-thiadiazolyl, 1, 2, 4-thiadiazolyl, 1, 2, 5-thiadiazolyl, 1, 3, 4-thiadiazolyl, 1, 3, 5-triazinyl, 1, 2, 4-triazinyl, 1, 2, 3-triazinyl, tetrazolyl, 1, 2, 4, 5-tetrazinyl, 1, 2, 3, 4-tetrazinyl, 1, 2, 3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazole, and the like. Preferred examples of the heteroaryl group in the present invention include furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, isobenzofuryl, indolyl, dibenzofuryl, dibenzothienyl, carbazolyl and derivatives thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole benzocarbazole, dibenzocarbazole or indolocarbazole.
Specific examples of the heteroarylene group in the present invention include divalent groups obtained by removing one hydrogen atom from the above-mentioned examples of the heteroaryl group.
Examples of the aryloxy group in the present invention include monovalent groups composed of the above aryl group, heteroaryl group and oxygen.
In the present specification, the term "C" means C1～C30Examples of the alkyl group include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, adamantyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2, 2, 2-trifluoroethyl and the like.
In the present specification, C3～C20Cycloalkyl includes monocycloalkyl and polycycloalkyl radicals, and may be, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like.
In the present specification, the term "C" means C1～C30Examples of alkoxy groups are: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy and the like, among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentyloxy, more preferably methoxy.
In the present specification, the term "C" means C2～C30Examples of alkenyl groups include: vinyl, propenyl, 1-butenyl, etc.; as C2～C30Examples of alkynyl groups include: ethynyl, propynyl, 1-butynyl and the like.
In the present specification, the term "C" means C1～C30Examples of silane groups may be those described above under C1～C30Specific examples of the silyl group substituted with the group exemplified in the alkyl group include: methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, t-butyldimethylsilyl, t-butyldiphenylsilyl and the likeAnd (4) clustering.
In the present specification, examples of the halogen include: fluorine, chlorine, bromine, iodine, and the like.
More specifically, R is the above-mentioned group1～R3The group (b) is preferably exemplified by hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2, 2, 2-trifluoroethyl, phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, bornyl, perylenyl, fluoranthenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, terphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, trimerization indenyl, isotridecylation indenyl, spirotrimerization indenyl, spiroisotridecylation indenyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalimidazolyl, kanilino, benzoxazolyl, naphthoxazolyl, anthraoxazolyl, phenanthroizolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzpyridazinyl, pyrimidinyl, benzopyrimidinyl, etc, Quinoxalinyl, 1, 5-diazahthranyl, 2, 7-diazpyrenyl, 2, 3-diazpyrenyl, 1, 6-diazpyrenyl, 1, 8-diazpyrenyl, 4, 5, 9, 10-tetraazaperylenyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbazinyl, phenanthrolinyl, 1, 2, 3-triazolyl, 1, 2, 4-triazolyl, benzotriazolyl, 1, 2, 3-oxadiazolyl, 1, 2, 4-dithiazolylOne of azolyl, 1, 2, 5-thiadiazolyl, 1, 2, 3-thiadiazolyl, 1, 2, 4-thiadiazolyl, 1, 2, 5-thiadiazolyl, 1, 3, 4-thiadiazolyl, 1, 3, 5-triazinyl, 1, 2, 4-triazinyl, 1, 2, 3-triazinyl, tetrazolyl, 1, 2, 4, 5-tetrazinyl, 1, 2, 3, 4-tetrazinyl, 1, 2, 3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, or a combination of two groups selected therefrom.
In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or a plurality of substituents, and when a plurality of substituents are present, different substituents may be selected from the group.
C above1～C17Amino group, C1～C17Carboxy, C1～C17Aldehyde group, C1～C17The ester group means a substituted amino group, carboxyl group, aldehyde group or ester group formed by the above-exemplified alkyl group, aryl group or heteroaryl group.
The following specifically describes each element of the present invention.
A compound having a structure represented by the general formula (A) and a compound of the general formula (3)
The organic light emitting device of the present invention has a structure which is a conventional structure, and is characterized in that the electron blocking layer contains a compound having a structure represented by the following general formula (A), the light emitting layer contains a compound having a structure represented by the following general formula (3) as a guest material,
Figure BDA0002783638290000071
wherein X is selected from O, S, CR5R6、NR7Or SiR8R9；
Ring A represents C6～C30Aromatic ring of (A) or (C)3～C30The heteroaromatic ring of (a) is a ring,
l is selected from single bond, substituted or unsubstituted C6～C30Arylene or substituted or unsubstituted C3～C30A heteroarylene group;
L1selected from single bond, substituted or unsubstituted C6～C11Arylene or substituted or unsubstituted C3～C11A heteroarylene group;
Ar2selected from substituted or unsubstituted C6～C30Aryl or substituted or unsubstituted C3～C30Heteroaryl of (A), Ar2The ring A to which it is attached may be substituted by-O-, -S-, -CR-10R11-、-NR12-or-SiR13R14-linked to form a ring;
R1～R3each independently selected from hydrogen, substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C3～C30Heteroaryl group, C1～C30Alkyl radical, C1～C30Alkoxy radical, C7～C30Arylalkoxy group, C3～C30Cycloalkyl radical, C2～C30Alkenyl radical, C2～C30Alkynyl, C1～C30A combination of one or more of silane groups, carbonyl groups, and R1、Ar2Can be connected into a ring;
m is an integer of 0-5, n is an integer of 0-7, p is an integer of 0-5, q is an integer of 0-5, and p + q is less than or equal to 5;
Ar1selected from substituted or unsubstituted C6～C30Aryl or substituted or unsubstituted C3～C23Heteroaryl of Ar1When having a substituent, the substituent is selected from the group consisting of halogen and C1～C30Alkyl radical, C3～C30Cycloalkyl radical, C2～C30Alkenyl radical, C1～C30Alkoxy or thioalkoxy, cyano, nitro, C1～C17Amino, carboxyl, aldehyde, ester, C6～C30Aryl radical, C3～C30A combination of one or more of heteroaryl groups,
as described aboveR5～R14Each independently selected from hydrogen and C1～C18Alkyl radical, C1～C18Alkoxy radical, C3～C30Cycloalkyl of, C2～C18Alkenyl radical, C2～C18Alkynyl, halogen, cyano, substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C3～C30Heteroaryl, substituted or unsubstituted C6～C30Arylamino, substituted or unsubstituted C3～C30One or more of a heteroaromatic amine group,
when each of the above-mentioned substituted or unsubstituted groups has a substituent, the substituent is selected from the group consisting of halogen and C1～C30Alkyl radical, C3～C30Cycloalkyl radical, C2～C30Alkenyl radical, C1～C30Alkoxy or thioalkoxy, cyano, nitro, C1～C30Amino, carboxyl, aldehyde, ester, C6～C30Aryl radical, C3～C30A combination of one or more of heteroaryl groups;
Figure BDA0002783638290000081
wherein, ring C1～C4Represents an aryl or heteroaryl ring; rB1～RB5Represents hydrogen or one or more chemically reasonable substituents selected from halogen, C1～C30Alkyl radical, C3～C30Cycloalkyl radical, C2～C30Alkenyl radical, C1～C30The alkoxy, aryl, heteroaryl, diarylamino and arylheteroarylamino can be mutually connected to form a ring, and can also be connected with other groups beside to form a ring; x1、X2Represents N or O when X1、X2When is O, C1、C4And substituents thereof are absent.
As ring A represents C6～C30Is an aromatic ring orC is3～C30The heteroaromatic ring of (a) may be the corresponding aromatic ring or heteroaromatic ring as exemplified in the general description, and among them, benzene ring, naphthalene ring, anthracene ring, phenanthrene ring are more preferable, benzene ring is further preferable, that is, the compound having a structure represented by the general formula (a') is preferable.
Figure BDA0002783638290000082
Preferred embodiments of the respective compounds of the present invention will be described from the viewpoint of further reducing the driving voltage of the device and improving the light-emitting efficiency and the device lifetime.
Preferably, the compound represented by the above general formula (A) is a compound represented by the following general formula (1),
Figure BDA0002783638290000083
wherein X is selected from O or S;
l and L1Selected from the group consisting of a single bond, phenylene, naphthylene, wherein when L is a single bond, one end thereof is attached to the 1-, 2-or 4-position of the dibenzofuran group or dibenzothiophene group; ar (Ar)2、R1～R3M, n, p, q have the same meanings as those expressed in the general formula (A); ar (Ar)1The same as that expressed in the general formula (A), except that Ar1Is not a carbazolyl group.
In the general formula (1), X is selected from O or S; l and L1Preferably selected from the group consisting of a single bond, phenylene, naphthylene, and when L is a single bond, one end thereof is attached to the 1-, 2-or 4-position of the dibenzofuran group or dibenzothiophene group; ar (Ar)2、R1～R3M, n, p, q have the same meanings as those expressed in the general formula (A); ar (Ar)1The same as that expressed in the general formula (A), except that Ar1Is not a carbazolyl group.
The compound of the general formula (1) is more preferably represented by one of the structures represented by the following general formulae (1-1) to (1-3) from the viewpoint of easy availability and better luminous efficiency,
Figure BDA0002783638290000091
in the following general formulae (1-1) to (1-3), Ar1Selected from one of the following substituted or unsubstituted groups:
Figure BDA0002783638290000092
ar of the following general formulae (1-1) to (1-3)2Independently selected from one of the following substituted or unsubstituted structures:
Figure BDA0002783638290000093
wherein R is15～R17Each independently selected from C1～C30Alkyl radical, C1～C30Alkoxy radical, C3～C30Cycloalkyl radical, C2～C30Alkenyl radical, C2～C30Alkynyl, substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C3～C30One of the heteroaryl groups is a heteroaryl group,
in the above, L and L1Preferably a single bond or phenylene group, R1Is hydrogen or phenyl, and p and q are 0 or 1.
Further preferably, the compound represented by the general formula (a) in the present invention is a compound represented by the following general formula (2);
Figure BDA0002783638290000101
wherein X is selected from O, S, CR5R6、NR7Or SiR8R9；
L1Selected from single bond, phenylene, naphthylene;
Ar2selected from substituted or unsubstituted C6～C30Aryl or substituted or unsubstituted C3～C30Heteroaryl of (A), Ar2The benzene ring to which it is attached may be replaced by-O-, -S-, -CR-10R11-、-NR12-or-SiR13R14-linked to form a ring;
ar mentioned above1、R1～R3、m、n、p、q、R5～R14The same meaning as that expressed in the general formula (A). .
The compound represented by the general formula (2) is a compound represented by the following general formula (2-1), general formula (2-2) or general formula (2-3) from the viewpoint of easy availability of raw materials and simple synthesis process;
Figure BDA0002783638290000102
in the general formula (2-1), the general formula (2-2) or the general formula (2-3), X is selected from CR5R6，L1Selected from single bonds or phenylene radicals, R5And R6Is methyl, Ar1Can be selected from one of phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, fluoranthenyl, carbazole, fluorene, dibenzofuran and dibenzothiophene or the combination of the groups, R1～R3Is hydrogen or phenyl, p, q, n are 0 or 1, Ar2One selected from phenyl, biphenyl, terphenyl, naphthyl, fluorene, anthryl, phenanthryl, fluoranthryl, carbazole, dibenzofuran, dibenzothiophene, or a combination of these groups. m is preferably 0 or 1, and more preferably 0.
A ring C in the BN type guest material having a structure represented by the general formula (3)1～C4Examples of the "aryl ring" include aryl rings having 6 to 30 carbon atoms, preferably aryl rings having 6 to 16 carbon atoms, more preferably aryl rings having 6 to 12 carbon atoms, and particularly preferably aryl rings having 6 to 10 carbon atoms. As ring C in the formula (3)1～C4The "heteroaryl ring" may be a C3-30 heteroaryl ring, preferably a C3-16 heteroaryl ringThe ring is more preferably a C3-12 heteroaryl ring, and particularly preferably a C3-10 aryl ring.
Specific "aryl ring" may include: benzene rings as monocyclic systems, biphenyl rings as bicyclic systems, naphthalene rings as condensed bicyclic systems, tribiphenyl rings (m-terphenyl, o-terphenyl, p-terphenyl) as tricyclic systems, acenaphthene rings, fluorene rings, phenalene rings, phenanthrene rings as condensed tricyclic systems, triphenylene rings, pyrene rings, and quaterpene rings (naphthacene rings) as condensed tricyclic systems, perylene rings, pentacene rings as condensed pentacyclic systems, and the like.
Specific examples of the "heteroaryl ring" include: a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, a phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, a carbazole ring, an acridine ring, a phenoxathiin ring, a phenoxazine ring, a phenothiazine ring, an indolizine ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a furazan ring, an anthracene ring, and the like.
The compound of the general formula (3) is preferably a compound represented by the following (3-1) to (3-4) from the viewpoints of availability of raw materials, simplicity of synthesis method, and capability of obtaining excellent light-emitting properties,
Figure BDA0002783638290000111
RC1～RC3each independently is halogen, C1～C30Alkyl radical, C3～C30Cycloalkyl radical, C2～C30Alkenyl radical, C1～C30Alkoxy of C6～C30Aryl radical, C3～C30Heteroaromatic compoundsBase, C12～C60Diarylamino, C6～C60An arylheteroarylamino group, u is independently an integer of 0 to 4, v is independently an integer of 0 to 5, w is independently an integer of 0 to 3, and when u, v and w are not 0, R's are more than oneC1Which may be the same or different, each RC1Between and each RC2Or R isC1And RC2May form a loop therebetween.
Here, "each RC1Between and each RC2Or R isC1And RC2May form a ring therebetween "means: with RC1For example, two RC1Between, or more than RC1And together with the benzene ring to which they are bonded, form an aliphatic or aromatic ring structure, wherein if an aromatic ring structure is formed, a fused ring structure may be formed together with the benzene ring to which they are bonded, for example, a naphthyl, anthryl, triphenylene, or the like structure.
In the above general formulae (3-1) to (3-4), R is preferredC1～RC3Each independently is a hydrogen atom, C1～C10Alkyl, more preferably RC1～RC3Each independently is a hydrogen atom, a methyl group, a tert-butyl group, a cyclohexyl group.
The compound represented by the general formula (3) in the present invention may be selected from any one or a combination of at least two of the following compounds, but is not limited thereto.
Figure BDA0002783638290000121
In the device of the present invention, specific compounds of the compound having a structure represented by the general formula (a) contained in the electron blocking layer may be any one or a combination of at least two of specific compounds A1 to a180, D1 to D178, E1 to E178, F1 to F180, G1 to G178, H1 to H178, and C1 to C2243, which are exemplified in the embodiment of the present invention.
Figure BDA0002783638290000122
Figure BDA0002783638290000131
Figure BDA0002783638290000141
Figure BDA0002783638290000151
Figure BDA0002783638290000161
Figure BDA0002783638290000171
Figure BDA0002783638290000181
Figure BDA0002783638290000191
Figure BDA0002783638290000201
Figure BDA0002783638290000211
Figure BDA0002783638290000221
Figure BDA0002783638290000231
Figure BDA0002783638290000241
Figure BDA0002783638290000251
Figure BDA0002783638290000261
Figure BDA0002783638290000271
Figure BDA0002783638290000281
Figure BDA0002783638290000291
Figure BDA0002783638290000301
Figure BDA0002783638290000311
Figure BDA0002783638290000321
Figure BDA0002783638290000331
Figure BDA0002783638290000341
Figure BDA0002783638290000351
Figure BDA0002783638290000361
Figure BDA0002783638290000371
Figure BDA0002783638290000381
Figure BDA0002783638290000391
Figure BDA0002783638290000401
Figure BDA0002783638290000411
Figure BDA0002783638290000421
Figure BDA0002783638290000431
Figure BDA0002783638290000441
Figure BDA0002783638290000451
Figure BDA0002783638290000461
Figure BDA0002783638290000471
Figure BDA0002783638290000481
Figure BDA0002783638290000491
Brief description of the Synthesis of the Compounds
The compound represented by the general formula (3) in the present invention can be produced according to the method disclosed in patent application CN 107851724A. The compounds having the structure represented by the general formula (a) in the present invention can be synthesized by referring to the following synthetic routes:
Figure BDA0002783638290000492
it should be noted that the above synthetic route is basically the same as that in patent application CN110317139, and can be obtained only by replacing the raw material containing the corresponding "L" group in the above step 2, and based on the common general knowledge and the disclosure of CN110317139, the compound of the present invention can be synthesized, and the details of the preparation method of the present invention are not repeated. It is to be noted that the method and route for obtaining the compound are not limited to those used in the present invention, and those skilled in the art can select other methods or routes to obtain the novel compound proposed in the present invention.
Organic light emitting device-related elements
The organic light emitting device of the present invention is characterized by using a combination of a specific electron blocking material and a light emitting guest material, wherein the structure and the manufacturing method of the organic light emitting device of the present invention are the same as those of the prior art. For example, each layer structure may be prepared by vacuum evaporation, or may be prepared by other methods, such as vacuum deposition.
The general manner of fabricating the devices of the present invention using vacuum deposition is described below.
The preparation method comprises the steps of cleaning a substrate, drying, pretreating, putting the substrate into a cavity, and sequentially carrying out vacuum deposition on 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.
Among them, the substrate is not particularly limited and may be a rigid substrate including a glass substrate, a Si substrate, etc., or a flexible substrate including a polyvinyl alcohol (PVA) film, a Polyimide (PD) film, a Polyester (PET) film, etc.; the substrate of the present invention is preferably a rigid glass substrate.
The anode is not particularly limited and may be prepared from a known material, and for example, a conductive compound, an alloy, a metal having a large work function, and a mixture of such materials may be preferable. Inorganic materials may be used, including metals or metal oxides, laminates of metals and metals or metals and non-metals, and the like, the metal oxides including Indium Tin Oxide (ITO), zinc oxide (ZnO), Indium Zinc Oxide (IZO), tin oxide (SnO), and the like, and the metals including gold, silver, copper, aluminum, and the like, which have a high work function; ITO is preferred as the anode of the present invention.
The hole transport region is not particularly limited, and the material of the hole transport region may be selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylenevinylene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives such as compounds shown below in HT-1 to HT-51; or any combination thereof.
Figure BDA0002783638290000501
Figure BDA0002783638290000511
Figure BDA0002783638290000521
The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more compounds of HT-1 to HT-51 described above, or one or more compounds of HI-1-HI-3 described below; one or more of the compounds HT-1 to HT-51 may also be used to dope one or more of the compounds HI-1-HI-3 described below.
Figure BDA0002783638290000531
The blue host material is not particularly limited, and may be prepared using a known material, for example, any one or at least two combinations selected from the following compounds represented by BFH-1 to BFH-17:
Figure BDA0002783638290000532
the electron transport layer is not particularly limited, and the electron transport layer material may be selected from, but is not limited to, combinations of one or more of ET-1 to ET-73 listed below. :
Figure BDA0002783638290000533
Figure BDA0002783638290000541
Figure BDA0002783638290000551
Figure BDA0002783638290000561
the cathode is not particularly limited, and may be prepared from known materials, such as magnesium silver mixture, metal such as LiF/Al, ITO, etc., metal mixture, oxide, etc., and Yb/magnesium silver mixture is preferred in the present invention.
Examples
For the purpose of facilitating an understanding of the present invention, the present invention will now be described by way of examples. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Synthetic examples
Synthesis example 1
Preparation method of compound A102
Figure BDA0002783638290000571
Synthesis of intermediate A102-M1
The compound 2-bromo-4-phenylaniline (50.0g,202mmol) synthesized in the above step, dibenzofuran-4-boronic acid (47.1g, 222mol), potassium carbonate (36.2g, 262mmol) were placed in a 1000mL three-necked flask, stirred well, then the air on the flask was replaced with nitrogen three times, palladium tetratriphenylphosphine (4.66g, 4.03mmol) was added to the reaction solution under nitrogen protection, and then the temperature was raised to 100 ℃ for reaction for 18 hours. After cooling, the reaction was poured into saturated aqueous ammonium chloride solution, extracted with ethyl acetate (500mL, three times), the organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated to give a reddish brown oil. The crude product was purified by silica gel column chromatography (petroleum ether/ethyl acetate, 10/1) to give a yellow solid. M/Z theoretical value: 335.1, M/Z found: 336.1(M + H).
Synthesis of intermediate A102-M2
Figure BDA0002783638290000572
Intermediate A102-M1(11.4g, 33.9mmol) and 4-bromobiphenyl (8.6g, 37.2mmol) were placed in a 250mL three-necked flask, followed by the addition of sodium tert-butoxide (3.9g, 40.6mmol) and toluene (150mL), after thorough stirring, nitrogen was used to replace the air in the flask, followed by the addition of the catalyst [1,1' -bis (diphenylphosphino) ferrocene ] dichloropalladium (248mg, 0.448mmol) and 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (278mg, 0.678mmol), and the reaction was allowed to warm to 100 ℃ for 16 h. After cooling to room temperature, the reaction mixture was poured into saturated aqueous ammonium chloride solution, extracted with ethyl acetate (100mL, three times), the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated to give a brown oil, which was purified by silica gel column chromatography (petroleum ether/dichloromethane, 15/1) to give a yellow solid. M/Z theoretical value: 487.1, M/Z found: 488.2(M + H).
Synthesis A102
Figure BDA0002783638290000573
Compound A102-M2(15g, 30.8mmol), 4-phenyl-6- (4-bromophenyl) dibenzofuran (13.4, 33.8mmol) and sodium tert-butoxide (3.55g, 36.9mmol) were charged in a 500mL three-necked flask with 200mL of toluene and dissolved with stirring. Then, the atmosphere in the flask was sufficiently changed with nitrogen, and then the catalysts tris (dibenzylideneacetone) dipalladium (282mg, 0.308mmol) and 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (505mg, 1.23mmol) were added to the reaction solution, and the temperature was raised to reflux reaction for 18 hours. After cooling, the reaction was poured into saturated aqueous ammonium chloride, extracted with ethyl acetate (200mL, three times), the organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated to a brownish-black oil. The crude product was purified by silica gel column chromatography (petroleum ether/dichloromethane, 15/1) to give a pale yellow solid. The solid was recrystallized twice from toluene and methanol and further purified by sublimation. M/Z theoretical value: 805.3, M/Z found: 806.3(M + H).
Synthesis example 2
Preparation method of compound A148
Figure BDA0002783638290000581
Compound A102-M2(15g, 30.8mmol), 2- (4-bromophenyl) -9, 9-dimethylfluorene (11.8g, 33.8mmol) and sodium tert-butoxide (3.55g, 36.9mmol) were charged in a 500mL three-necked flask with 200mL toluene and dissolved with stirring. Then, the atmosphere in the flask was sufficiently changed with nitrogen, and then the catalysts tris (dibenzylideneacetone) dipalladium (282mg, 0.308mmol) and 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (505mg, 1.23mmol) were added to the reaction solution, and the temperature was raised to reflux reaction for 18 hours. After cooling, the reaction was poured into saturated aqueous ammonium chloride, extracted with ethyl acetate (200mL, three times), the organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated to a brownish-black oil. The crude product was purified by silica gel column chromatography (petroleum ether/dichloromethane, 15/1) to give a pale yellow solid. The solid was recrystallized twice from toluene and methanol and further purified by sublimation. M/Z theoretical value: 755.3, M/Z found: 756.3(M + H).
Synthesis example 3
Preparation method of compound C378
Figure BDA0002783638290000582
Compound A102-M2(15g, 30.8mmol), 4- (3-bromophenyl) dibenzofuran (10.9, 33.8mmol) and sodium tert-butoxide (3.55g, 36.9mmol) were charged in a 500mL three-necked flask containing 200mL of toluene and dissolved with stirring. Then, the atmosphere in the flask was sufficiently changed with nitrogen, and then the catalysts tris (dibenzylideneacetone) dipalladium (282mg, 0.308mmol) and 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (505mg, 1.23mmol) were added to the reaction solution, and the temperature was raised to reflux reaction for 18 hours. After cooling, the reaction was poured into saturated aqueous ammonium chloride, extracted with ethyl acetate (200mL, three times), the organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated to a brownish-black oil. The crude product was purified by silica gel column chromatography (petroleum ether/dichloromethane, 15/1) to give a pale yellow solid. The solid was recrystallized twice from toluene and methanol and further purified by sublimation. M/Z theoretical value: 729.3, M/Z found: 730.2(M + H).
Synthesis example 4
Compound C106 was synthesized based on the method of synthesis example 61 with patent application CN 110317139.
Synthesis examples 5 to 8
According to the same method as the examples in the patent application CN107851724A, the compounds BFD-1, BFD-2, BFD-3 and BFD-10 are synthesized.
Example 1
The embodiment provides an organic electroluminescent device, and the preparation method comprises the following steps:
the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
the glass substrate with the anode is placed in a vacuum chamber, the vacuum chamber is vacuumized to be less than 1 x 10 < -5 > Pa, a10 nm HT-4: HI-3(97/3, w/w) mixture is subjected to vacuum thermal evaporation on the anode layer film in sequence to be used as a hole injection layer, a 60nm compound HT-4 is used as a hole transport layer, A1 nm compound A102 is used as an electron blocking layer, a 20nm compound BFH-1: BFD-1(100:3, w/w) binary mixture is used as a light emitting layer, a 25nm compound ET-69: ET-57(50/50, w/w) mixture is used as an electron transport layer, 1nm LiF is used as an electron injection layer, and 150nm metal aluminum is used as a cathode. The total evaporation rate of all the organic layers and LiF is controlled at 0.1 nm/s, and the evaporation rate of the metal electrode is controlled at 1 nm/s.
The organic electroluminescent device provided in example 1 has a structure as shown in fig. 1, and includes an anode 1, a hole injection layer 2, a hole transport layer 3, an electron blocking layer 4, a light emitting layer 5, an electron transport layer 6, an electron injection layer 7, and a cathode 8.
Example 2
The only difference from example 1 is that the compound a102 has a deposition thickness of 3 nm.
Example 3
The only difference from example 1 is that the compound a102 was deposited to a thickness of 5 nm.
Example 4
The only difference from example 1 is that the compound a102 has a vapor deposition thickness of 10 nm.
Example 5
The only difference from example 1 is that the compound a102 has a vapor deposition thickness of 20 nm.
Example 6
The only difference from example 1 is that the compound a102 has a vapor deposition thickness of 40 nm.
Example 7
The only difference from example 1 is that the compound a102 has a vapor deposition thickness of 80 nm.
Example 8
The only difference from example 1 is that the compound a102 has a deposition thickness of 100 nm.
Example 9
The only difference from example 1 is that compound a102 is replaced by C378.
Example 10
The only difference from example 3 is that compound a102 is replaced by C378.
Example 11
The only difference from example 5 is that compound a102 is replaced by C378.
Example 12
The only difference from example 8 is that compound a102 is replaced by C378.
Example 13
The only difference from example 3 is that compound a102 is replaced by a102+ a148 and the two materials are doped 1: 1.
Example 14
The only difference from example 3 is that compound a102 is replaced by a148+ C378, and the two materials are doped 1: 1.
Example 15
The only difference from example 3 is that compound a102 is replaced by C378+ C106, and the two materials are doped 1: 1.
Example 16
The only difference from example 3 is that the light-emitting layer guest material was replaced with BFD-2.
Example 17
The only difference from example 3 is that the light-emitting layer guest material was replaced with BFD-3.
Example 18
The only difference from example 3 is that the light-emitting layer guest material was replaced with BFD-10.
Comparative example 1
The only difference from example 3 is that Compound A102 is replaced by
Figure BDA0002783638290000601
Comparative example 2
The only difference from example 3 is that the guest material of the light-emitting layer is replaced with
Figure BDA0002783638290000602
Among them, the BD2 compound is a commonly known guest material.
Comparative example 3
The only difference from example 3 is that compound a102 was replaced by C378.
Comparative example 4
The only difference from example 3 is that the compound a102 has a vapor deposition thickness of 0.5 nm.
Comparative example 5
The only difference from example 3 is that the compound a102 was deposited with a thickness of 200 nm.
Comparative example 6
The only difference from example 10 is that the compound C378 has a deposition thickness of 0.5 nm.
Comparative example 7
The only difference from example 10 is that compound C378 has a deposition thickness of 200 nm.
Comparative example 8
The only difference from example 3 is that the guest material of the light-emitting layer was replaced with BD3
Figure BDA0002783638290000611
The BD3 compound is a commonly known guest material.
Comparative example 9
The only difference from example 3 is that the guest material of the light-emitting layer was replaced with BD4
Figure BDA0002783638290000612
The BD4 compound is a commonly known guest material.
Performance testing
(1) The organic electroluminescent devices prepared in examples and comparative examples were measured for driving voltage and current efficiency and lifetime of the devices at the same luminance using a photoradiometer model PR 750 from phoresearch, a luminance meter model ST-86LA (photoelectric instrument factory, university of beijing) and a Keithley4200 test system. Specifically, the luminance of the organic electroluminescent device was measured at 1000cd/m blue light as the voltage was boosted at a rate of 0.1V per second2The voltage is the driving voltage (V), and the current density at the moment is measured; the ratio of brightness to current density is the current efficiency (CE, cd/A);
(2) the life test of LT95 is as follows: blue light of 3000cd/m is measured by ST-86LA type luminance meter (photoelectric instrument factory of Beijing university)2Next, the time, in hours, at which the luminance of the organic electroluminescent device was decreased to 95% of the initial luminance was measured while maintaining a constant current. The other examples and comparative examples give relative life values with the life time of example 1 set as 100%.
The test results are shown in table 1.
TABLE 1
Figure BDA0002783638290000621
As can be seen from table 1, the compound having the structure shown in the general formula (a) and the blue guest material shown in the general formula (3) are used in combination, so that the driving voltage can be reduced, the current efficiency can be improved, the lifetime can be remarkably prolonged, and the performance of the OLED display device can be improved.
The applicant states that the present invention is illustrated by the above examples to show the detailed process equipment and process flow of the present invention, but the present invention is not limited to the above detailed process equipment and process flow, i.e. it does not mean that the present invention must rely on the above detailed process equipment and process flow to be implemented. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.

Claims (11)

1. An organic light-emitting device comprising a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises an electron-blocking layer comprising a compound having a structure represented by the following general formula (A) and a light-emitting layer comprising a compound having a structure represented by the following general formula (3) as a guest material,
Figure FDA0002783638280000011
wherein X is selected from O, S, CR5R6、NR7Or SiR8R9；
Ring A represents C6～C30Aromatic ring of (A) or (C)3～C30The heteroaromatic ring of (a) is a ring,
l is selected from single bond, substituted or unsubstituted C6～C30Arylene or substituted or unsubstituted C3～C30A heteroarylene group;
L1selected from single bond, substituted or unsubstituted C6～C11Arylene or substituted or unsubstituted C3～C11A heteroarylene group;
Ar2selected from substituted or unsubstituted C6～C30Aryl or substituted or unsubstituted C3～C30Heteroaryl of Ar2The A ring to which it is attached may be replaced by-O-, -S-, -CR-10R11-、-NR12-or-SiR13R14-linked to form a ring;
R1～R3each independently selected from hydrogen, substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C3～C30Heteroaryl group, C1～C30Alkyl radical, C1～C30Alkoxy radical, C7～C30Arylalkoxy group, C3～C30Cycloalkyl radical, C2～C30Alkenyl radical, C2～C30Alkynyl, C1～C30A combination of one or more of silane groups, carbonyl groups, and R1、Ar2Can be connected into a ring;
m is an integer of 0-5, n is an integer of 0-7, p is an integer of 0-5, q is an integer of 0-5, and p + q is less than or equal to 5;
Ar1selected from substituted or unsubstituted C6～C30Aryl or substituted or unsubstituted C3～C23Heteroaryl of Ar1When having a substituent, the substituent is selected from the group consisting of halogen and C1～C30Alkyl radical, C3～C30Cycloalkyl radical, C2～C30Alkenyl radical, C1～C30Alkoxy or thioalkoxy, cyano, nitro, C1～C17Amino, carboxyl, aldehyde, ester, C6～C30Aryl radical, C3～C30A combination of one or more of heteroaryl groups,
r is as defined above5～R14Each independently selected from hydrogen and C1～C18Alkyl radical, C1～C18Alkoxy radical, C3～C30Cycloalkyl of, C2～C18Alkenyl radical, C2～C18Alkynyl, halogen, cyano, substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C3～C30Heteroaryl, substituted or unsubstituted C6～C30Arylamino, substituted or unsubstituted C3～C30One or more of a heteroaromatic amine group,
when each of the above-mentioned substituted or unsubstituted groups has a substituent, the substituent is selected from the group consisting of halogen and C1～C30Alkyl radical, C3～C30Cycloalkyl radical, C2～C30Alkenyl radical, C1～C30Alkoxy or thioalkoxy, cyano, nitro, C1～C30Amino, carboxyl, aldehyde, ester, C6～C30Aryl radical, C3～C30A combination of one or more of heteroaryl groups;
Figure FDA0002783638280000021
wherein, ring C1～C4Represents an aryl or heteroaryl ring; rB1～RB5Represents hydrogen or one or more chemically reasonable substituents selected from halogen, C1～C30Alkyl radical, C3～C30Cycloalkyl, C2～C30Alkenyl radical, C1～C30Alkoxy group of (C)6～C30Aryl radical, C3～C30Heteroaryl group, C12～C60Diarylamino, C6～C60Aryl heteroaryl amino, which can be connected with each other to form a ring, or can be connected with other groups beside to form a ring; x1、X2Represents N or O when X1、X2When is O, C1、C4And substituents thereof are absent.
2. The organic light-emitting device according to claim 1, wherein the compound having a structure represented by the general formula (A) is a compound having a structure represented by the following general formula (A'),
Figure FDA0002783638280000022
wherein X is selected from O, S, CR5R6、NR7Or SiR8R9；
L is selected from single bond, substituted or unsubstituted C6～C30Arylene or substituted or unsubstituted C3～C30A heteroarylene group;
L1selected from single bond, substituted or unsubstituted C6～C11Arylene or substituted or unsubstituted C3～C11A heteroarylene group;
Ar2selected from substituted or unsubstituted C6～C30Aryl or substituted or unsubstituted C3～C30Heteroaryl of Ar2The benzene ring to which it is attached may be replaced by-O-, -S-, -CR-10R11-、-NR12-or-SiR13R14-linked to form a ring;
R1～R3each independently selected from hydrogen, substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C3～C30Heteroaryl group, C1～C30Alkyl radical, C1～C30Alkoxy radical, C7～C30Arylalkoxy group, C3～C30Cycloalkyl radical, C2～C30Alkenyl radical, C2～C30Alkynyl, C1～C30A combination of one or more of silane groups, carbonyl groups, and R1、Ar2Can be connected into a ring;
m is an integer of 0-5, n is an integer of 0-7, p is an integer of 0-5, q is an integer of 0-5, and p + q is less than or equal to 5;
Ar1selected from substituted or unsubstituted C6～C30Aryl or substituted or unsubstituted C3～C23Heteroaryl of (A), Ar1When having a substituent, the substituent is selected from the group consisting of halogen and C1～C30Alkyl radical, C3～C30Cycloalkyl, C2～C30Alkenyl radical, C1～C30Alkoxy or thioalkoxy, cyano, nitro, C1～C17Amino, carboxyl, aldehyde group, ester group, C6～C30Aryl radical, C3～C30A combination of one or more of heteroaryl groups,
r is as defined above5～R14Each independently selected from hydrogen and C1～C18Alkyl radical, C1～C18Alkoxy radical, C3～C30Cycloalkyl of, C2～C18Alkenyl radical, C2～C18Alkynyl, halogen, cyano, substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C3～C30Heteroaryl, substituted or unsubstituted C6～C30Arylamino, substituted or unsubstituted C3～C30One or more of a heteroaromatic amine group,
when each of the above-mentioned substituted or unsubstituted groups has a substituent, the substituent is selected from the group consisting of halogen and C1～C30Alkyl radical, C3～C30Cycloalkyl radical, C2～C30Alkenyl radical, C1～C30Alkoxy or thioalkoxy, cyano, nitro, C1～C30Amino, carboxyl, aldehyde, ester, C6～C30Aryl radical, C3～C30A combination of one or more of heteroaryl groups.
3. The organic light-emitting device according to claim 1, wherein the compound having a structure represented by formula (A) is a compound represented by the following general formula (1),
Figure FDA0002783638280000031
wherein X is selected from O or S;
l and L1Selected from the group consisting of a single bond, phenylene, naphthylene, wherein when L is a single bond, one end thereof is attached to the 1-, 2-or 4-position of the dibenzofuran group or dibenzothiophene group;
Ar2、R1～R3m, n, p, q have the same meanings as those expressed in the general formula (A);
Ar1the same as that expressed in the general formula (A), except that Ar1Is not a carbazolyl group.
4. The organic light-emitting device according to claim 3, wherein the compound represented by the general formula (1) is a compound having a structure represented by the following general formula (1-1), (1-2) or (1-3),
Figure FDA0002783638280000032
Ar1selected from one of the following substituted or unsubstituted groups:
Figure FDA0002783638280000041
Ar2independently selected from one of the following substituted or unsubstituted structures:
Figure FDA0002783638280000042
wherein R is15～R17Each independently selected from C1～C30Alkyl radical, C1～C30Alkoxy radical, C3～C30Cycloalkyl radical, C2～C30Alkenyl radical, C2～C30Alkynyl, substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C3～C30One of the heteroaryl groups is a heteroaryl group,
said substitution of each of the above substituted or unsubstituted groups means by a group selected from halogen, C1～C30Alkyl radical, C3～C30Cycloalkyl radical, C2～C30Alkenyl, cyano and nitro.
5. The organic light emitting device of claim 4, wherein L and L1Is a single bond or phenylene, R1Is hydrogen or phenyl, and p and q are 0 or 1.
6. The organic light-emitting device according to claim 1, wherein the compound having a structure represented by formula (A) is a compound represented by general formula (2),
Figure FDA0002783638280000043
wherein X is selected from O, S, CR5R6、NR7Or SiR8R9；
L1Selected from single bond, phenylene, naphthylene;
Ar2selected from substituted or unsubstituted C6～C30Aryl or substituted or unsubstituted C3～C30Heteroaryl of Ar2The benzene ring to which it is attached may be replaced by-O-, -S-, -CR-10R11-、-NR12-or-SiR13R14-linked to form a ring;
ar above1、R1～R3、m、n、p、q、R5～R14The same meaning as that expressed in the general formula (A).
7. The organic light-emitting device according to claim 6, wherein the compound represented by the general formula (2) is a compound represented by the following general formula (2-1), general formula (2-2), or general formula (2-3);
Figure FDA0002783638280000051
x is selected from CR5R6，L1Selected from a single bond or phenylene, R5And R6Is a methyl group, and the compound is,
Ar1one or a combination of phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracyl, fluoranthenyl, carbazolyl, fluorene, dibenzofuranyl and dibenzothiophenyl,
R1～R3is hydrogen or phenyl, p, q, n, m are 0 or 1,
Ar2one selected from phenyl, biphenyl, terphenyl, naphthyl, fluorene, anthryl, phenanthryl, fluoranthenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, or a combination thereof.
8. The organic light-emitting device according to claim 1, wherein the compound having a structure represented by the general formula (a) is a compound represented by the following formula (a):
Figure FDA0002783638280000061
Figure FDA0002783638280000071
Figure FDA0002783638280000081
Figure FDA0002783638280000091
Figure FDA0002783638280000101
Figure FDA0002783638280000111
Figure FDA0002783638280000121
Figure FDA0002783638280000131
Figure FDA0002783638280000141
Figure FDA0002783638280000151
Figure FDA0002783638280000161
Figure FDA0002783638280000171
Figure FDA0002783638280000181
Figure FDA0002783638280000191
Figure FDA0002783638280000201
Figure FDA0002783638280000211
Figure FDA0002783638280000221
Figure FDA0002783638280000231
Figure FDA0002783638280000241
Figure FDA0002783638280000251
Figure FDA0002783638280000261
Figure FDA0002783638280000271
Figure FDA0002783638280000281
Figure FDA0002783638280000291
Figure FDA0002783638280000301
Figure FDA0002783638280000311
Figure FDA0002783638280000321
Figure FDA0002783638280000331
Figure FDA0002783638280000341
Figure FDA0002783638280000351
Figure FDA0002783638280000361
Figure FDA0002783638280000371
Figure FDA0002783638280000381
Figure FDA0002783638280000391
Figure FDA0002783638280000401
Figure FDA0002783638280000411
Figure FDA0002783638280000421
Figure FDA0002783638280000431
Figure FDA0002783638280000441
Figure FDA0002783638280000451
Figure FDA0002783638280000461
Figure FDA0002783638280000471
Figure FDA0002783638280000481
Figure FDA0002783638280000491
Figure FDA0002783638280000501
Figure FDA0002783638280000511
Figure FDA0002783638280000521
Figure FDA0002783638280000531
Figure FDA0002783638280000541
Figure FDA0002783638280000551
Figure FDA0002783638280000561
Figure FDA0002783638280000571
Figure FDA0002783638280000581
Figure FDA0002783638280000591
Figure FDA0002783638280000601
Figure FDA0002783638280000611
Figure FDA0002783638280000621
Figure FDA0002783638280000631
Figure FDA0002783638280000641
Figure FDA0002783638280000651
Figure FDA0002783638280000661
Figure FDA0002783638280000671
Figure FDA0002783638280000681
Figure FDA0002783638280000691
Figure FDA0002783638280000701
Figure FDA0002783638280000711
Figure FDA0002783638280000721
Figure FDA0002783638280000731
Figure FDA0002783638280000741
Figure FDA0002783638280000751
Figure FDA0002783638280000761
Figure FDA0002783638280000771
Figure FDA0002783638280000781
Figure FDA0002783638280000791
Figure FDA0002783638280000801
Figure FDA0002783638280000811
Figure FDA0002783638280000821
Figure FDA0002783638280000831
Figure FDA0002783638280000841
Figure FDA0002783638280000851
Figure FDA0002783638280000861
Figure FDA0002783638280000871
Figure FDA0002783638280000881
Figure FDA0002783638280000891
Figure FDA0002783638280000901
Figure FDA0002783638280000911
Figure FDA0002783638280000921
Figure FDA0002783638280000931
Figure FDA0002783638280000941
Figure FDA0002783638280000951
Figure FDA0002783638280000961
Figure FDA0002783638280000971
Figure FDA0002783638280000981
Figure FDA0002783638280000991
Figure FDA0002783638280001001
Figure FDA0002783638280001011
Figure FDA0002783638280001021
Figure FDA0002783638280001031
Figure FDA0002783638280001041
Figure FDA0002783638280001051
Figure FDA0002783638280001061
Figure FDA0002783638280001071
Figure FDA0002783638280001081
Figure FDA0002783638280001091
Figure FDA0002783638280001101
Figure FDA0002783638280001111
Figure FDA0002783638280001121
Figure FDA0002783638280001131
Figure FDA0002783638280001141
Figure FDA0002783638280001151
Figure FDA0002783638280001161
Figure FDA0002783638280001171
Figure FDA0002783638280001181
Figure FDA0002783638280001191
Figure FDA0002783638280001201
Figure FDA0002783638280001211
Figure FDA0002783638280001221
Figure FDA0002783638280001231
Figure FDA0002783638280001241
Figure FDA0002783638280001251
Figure FDA0002783638280001261
Figure FDA0002783638280001271
Figure FDA0002783638280001281
Figure FDA0002783638280001291
Figure FDA0002783638280001301
Figure FDA0002783638280001311
Figure FDA0002783638280001321
Figure FDA0002783638280001331
Figure FDA0002783638280001341
Figure FDA0002783638280001351
Figure FDA0002783638280001361
Figure FDA0002783638280001371
Figure FDA0002783638280001381
Figure FDA0002783638280001391
Figure FDA0002783638280001401
Figure FDA0002783638280001411
Figure FDA0002783638280001421
Figure FDA0002783638280001431
Figure FDA0002783638280001441
Figure FDA0002783638280001451
Figure FDA0002783638280001461
Figure FDA0002783638280001471
Figure FDA0002783638280001481
Figure FDA0002783638280001491
9. the organic light-emitting device according to claim 1 or 8, wherein the compound having a structure represented by the general formula (3) is a compound represented by any one of the following (3-1) to (3-4),
Figure FDA0002783638280001501
RC1～RC3each independently is halogen, C1～C30Alkyl radical, C3～C30Cycloalkyl radical, C2～C30Alkenyl radical, C1～C30Alkoxy of C6～C30Aryl radical, C3～C30Heteroaryl group, C12～C60Diarylamino, C6～C60An arylheteroarylamino group, u is independently an integer of 0 to 4, v is independently an integer of 0 to 5, w is independently an integer of 0 to 3, and when u, v, and w are not 0, R's are more than oneC1A plurality of R's, which may be the same or differentC2May be the same or different, each RC1Each RC2Or R isC1And RC2May form a loop therebetween.
10. The organic light emitting device of claim 9, wherein RC1～RC3Each independently is a hydrogen atom, C1～C10Alkyl, preferably RC1～RC3Hydrogen atom, methyl, tert-butyl and cyclohexyl.
11. The organic light-emitting device according to any one of claims 1 to 8 and 10, wherein the thickness of the electron blocking layer is 1 to 100nm, preferably 5 to 20 nm.
CN202011290380.9A 2020-11-17 2020-11-17 Organic light emitting device Pending CN114512618A (en)

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