Narrow-spectrum pure green light electroluminescent device luminescent layer composition and application thereof
By using a combination of narrow spectrum pure green light organic electroluminescent compound and sulfur-containing or selenium sensitizer in electroluminescent devices, the lack of narrow spectrum pure green light emitting layer composition is solved, and high efficiency and long life are achieved The narrow spectrum pure green light emission meets the high color purity requirements in the display field.
Patent Information
- Application Number
- CN202411308853.1
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2024-09-18
- Publication Date
- 2025-01-03
AI Technical Summary
The prior art lacks a narrow spectrum pure green photoelectric luminescent device light emitting layer composition, which is difficult to meet the requirements of the display field for high color purity.
Provided is a light emitting layer composition of a narrow spectrum pure green photoelectroluminescent device, including a narrow spectrum pure green light organic electroluminescent compound and a sensitizer containing sulfur or selenium atoms, by combining preferred compound structures and sensitizers , realize the emission of pure green light with narrow spectrum and high pure color.
It realizes high external quantum efficiency and long life of electroluminescent devices, and the compound preparation process is simple and easy to perform, suitable for mass production.
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Figure CN119255633A_ABST
Abstract
Description
Technical Field
[0001] The invention relates to the field of organic electroluminescent materials, and in particular to a narrow-spectrum pure green light electroluminescent device luminescent layer composition and application thereof. Background Art
[0002] Organic light-emitting diodes (OLEDs) have been attracting attention from academia and industry as a new technology in the field of display and lighting due to their advantages such as low energy consumption, wide viewing angle, brilliant colors, and flexibility. In 1987, Dr. Qingyun Deng and others from Eastman Kodak invented the sandwich-type organic double-layer thin-film electroluminescent device, which has since set off a technological boom in OLEDs research worldwide. Fluorescent organic light-emitting diodes are the earliest developed organic light-emitting devices. Traditional fluorescent luminescent materials often have a large radiation transition rate (k r ) and high photoluminescence quantum efficiency (PLQY), have been widely studied and developed. However, although traditional fluorescent materials are rich in variety, they can only utilize 25% of the excitons in the singlet state (S1), and 75% of the excitons in the triplet state (T1) are restricted by spin prohibition and can only return to the ground state by non-radiative transition. In order to further utilize T1 excitons, researchers have developed a thermally activated delayed fluorescence (TADF) strategy, using TADF materials as the luminescent material in the device, and taking advantage of the efficient reverse intersystem crossing process of TADF materials to fully utilize T1 excitons, thereby improving OLED performance.
[0003] Different from the localized state (LE) emission of traditional fluorescent molecules, the emission of TADF materials mainly originates from the transition of the intramolecular charge transfer state (ICT), so it is easily affected by the vibration and rotation between the donor and the acceptor in the molecule, which makes the emission spectrum wider and difficult to meet the requirements of high color purity in the display field. A narrow spectrum pure green light electroluminescent device light-emitting layer composition is urgently needed in the related technology. Summary of the invention
[0004] The purpose of the present invention is to overcome the problem in the related art of lacking a narrow-spectrum pure green light electroluminescent device luminescent layer composition, and further provide a narrow-spectrum pure green light electroluminescent device luminescent layer composition and its application.
[0005] In this application, the term "substituent" has its ordinary meaning as known in the art and refers to a chemical moiety that is covalently attached to or, where appropriate, fused to a parent core group.
[0006] In the present application, the term "substituted or unsubstituted" means that the functional group recorded after the term may or may not have a substituent (hereinafter, for ease of description, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl or non-substituted aryl having a substituent Rc. Wherein the above-mentioned substituent, i.e., Rc, can be, for example, deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C1-C60 heteroaryl, and optionally, for example, deuterium, halogen group, cyano, alkyl, haloalkyl, trialkylsilyl, deuterated alkyl, aryl, heteroaryl, etc. Of course, the number of substituents Rc can be one or more. When two substituents Rc are connected to the same atom, the two substituents Rc can exist independently or be connected to each other to form a ring with the atom; when two adjacent substituents Rc exist on a functional group, the adjacent substituents Rc can exist independently or be fused to form a ring with the functional group to which they are connected.
[0007] In the present application, the term "alkyl" refers to a saturated hydrocarbon group, whether used as part of other terms or alone, which can be straight or branched. The term "C1-C60 alkyl" is derived from a monovalent substituent of a straight or branched saturated hydrocarbon having 1 to 60 carbon atoms, preferably 1 to 40 carbon atoms, and more preferably 1 to 20 carbon atoms, of course, examples thereof include but are not limited to methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl and hexyl.
[0008] In the present application, the term "C3-C60 cycloalkyl" refers to a ring alkyl group consisting of at least 3 atoms, and further refers to a cycloalkyl group derived from a monocyclic hydrocarbon or polycyclic hydrocarbon having 3 to 60 ring main chain carbon atoms, preferably 3 to 40 carbon atoms, and more preferably 3 to 20 carbon atoms. Of course, the cycloalkyl group includes but is not limited to cyclopropyl, cyclobutyl, adamantyl, etc.
[0009] In the present application, the terms "aryl" and "arylene" include monocyclic, polycyclic or condensed-ring aromatic groups, the rings may be interrupted by short non-aromatic units, and may contain spiro structures. Aryl groups include but are not limited to phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracenyl, fluorenyl, spirobifluorenyl, etc., and arylene groups include but are not limited to phenylene, biphenylene, terphenylene, naphthyl, phenanthryl, anthracenyl, fluorenyl, spirobifluorenyl, etc.
[0010] In the present application, the term "heteroaryl" includes monocyclic, polycyclic or condensed-ring heteroaryl groups, wherein the rings may be interrupted by short non-aromatic units, wherein the heteroatoms include nitrogen, oxygen, and sulfur, and the heteroaryl groups in the present application include but are not limited to furanyl, phenylthio, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazolyl, pyridyl, pyrazinyl, pyrimid ... pyridyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl , and derivatives thereof; heteroarylene groups include, but are not limited to, furanylene, phenylthioene, pyrrolylene, imidazolylene, pyrazolylene, thiazolylene, thiadiazolylene, isothiazolylene, isoxazolylene, oxazolylene, oxadiazolylene, triazinylene, tetrazinylene, triazolylene, tetrazolylene, furazolylene, pyridinylene, pyrazinylene, pyrimidinylene, pyridazinylene, benzofuranylene, benzothiophenylene, isobenzofuranylene, dibenzofuranylene, Furanyl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, and derivatives thereof. As used in the present invention, the term "substituted" refers to a hydrogen atom in a compound that is replaced by another substituent. The position is not limited to a specific position, as long as the hydrogen at the position can be replaced by a substituent. When two or more substituents are present, the two or more substituents may be the same or different.
[0011] In the present application, the term "halogen" refers to an atom selected from fluorine, chlorine, bromine and iodine.
[0012] In the present application, unless otherwise specified, a hydrogen atom includes protium, deuterium and tritium.
[0013] In the present application, the range of carbon atom number is defined in the definition of the group, and the carbon atom number is any integer within the defined range. For example, C6-C60 aromatic group, the carbon atom number representing the aromatic group can be any integer within the range of 6-60, such as 6, 8, 10, 13, 15, 17, 20, 22, 25 or 30, etc.
[0014] In the present application, if a group is not limited to being substituted or unsubstituted, it means being unsubstituted.
[0015] The scheme adopted by the present invention is as follows:
[0016] The invention provides a narrow-spectrum pure green light electroluminescent device luminescent layer composition, comprising a narrow-spectrum pure green light organic electroluminescent compound and a sensitizer containing sulfur or selenium atoms.
[0017] Preferably, the narrow spectrum pure green light organic electroluminescent compound has the structure shown below:
[0018]
[0019] Wherein, Ar1 is a substituted or unsubstituted C5-C10 aryl ring, or a substituted or unsubstituted C3-C6 aryl heterocycle;
[0020] Ar2 is a substituted or unsubstituted C5-C60 aryl ring, or a substituted or unsubstituted C3-C60 aryl heterocycle;
[0021] Ar3 is a substituted or unsubstituted C7-C60 fused aromatic ring, or a substituted or unsubstituted C3-C60 aromatic heterocyclic ring;
[0022] Ar4 is absent, or is a substituted or unsubstituted C5-C60 aryl ring, or a substituted or unsubstituted C3-C80 aryl heterocycle;
[0023] X1 and X2 are each independently selected from -O-, -S-, -Se- or -N(R1)-; R1 is selected from any one of H, D, F, Cl, Br, I, benzyl, ester group, amide group, carbonyl group, aldehyde group, carbonyl group, nitro group, C1-C10 alkyl group, C1-10 alkoxy group, C1-10 alkylamino group, C3-C30 cycloalkyl group, C1-C30 alkylthio group, C6-C30 aryl group, C3-C30 heteroaryl group, cyano-substituted C1-C10 alkyl group, C6-C30 aryl group, C3-C30 heteroaryl group;
[0024] Among them, the substituents in the substituted C5-C10 aryl ring, substituted C3-C6 aryl heterocycle, substituted C7-C60 condensed aromatic ring, substituted C5-C60 aryl ring, substituted C3-C60 aryl heterocycle, and substituted C3-C80 aryl heterocycle are selected from H, D, F, Cl, Br, I, nitrile, acyl, alkoxy, C1-C30 alkyl, C3-C30 cycloalkyl, C1-C30 alkylthio, C6-C30 aryl, and C3-C30 heteroaryl.
[0025] for Ring E is formed by connecting two adjacent carbon atoms on X2, B and Ar3 and two adjacent carbon atoms on Ar2 to form a ring; Ring F is formed by connecting two adjacent carbon atoms on X1, B and Ar1 and two adjacent carbon atoms on Ar2 to form a ring. Similar structures in this application are similar to this explanation.
[0026] Preferably, the narrow spectrum pure green light organic electroluminescent compound has the structure shown below:
[0027]
[0028] Wherein, Ar5 is a substituted or unsubstituted C7-C60 aryl ring, or a substituted or unsubstituted C3-C60 aryl heterocycle;
[0029] The substituents in the substituted C7-C60 aryl ring and the substituted C5-C60 aryl ring are selected from H, D, F, Cl, Br, I, nitrile, acyl, alkoxy, C1-C30 alkyl, C3-C30 cycloalkyl, C1-C30 alkylthio, C6-C30 aryl, and C3-C30 heteroaryl;
[0030] The definitions of Ar2, Ar3, X1, and X2 are the same as those in claim 1.
[0031] Preferably, the structure of Ar4 is as shown in the following formula (3):
[0032]
[0033] Wherein, Ar5 is a substituted or unsubstituted C5-C60 aryl ring, or a substituted or unsubstituted C3-C60 aryl heterocycle;
[0034] Ar6 is a substituted or unsubstituted C7-C60 aryl ring, or a substituted or unsubstituted C3-C60 aryl heterocycle;
[0035] Ar4 is absent, or is a substituted or unsubstituted C5-C60 aryl ring, or a substituted or unsubstituted C3-C80 aryl heterocycle;
[0036] X3 and X4 are each independently selected from -O-, -S-, -Se- or -N(R1)-; R1 is selected from any one of H, D, F, Cl, Br, I, benzyl, ester, amide, carbonyl, aldehyde, carbonyl, nitro, C1-C10 alkyl, C1-10 alkoxy, C1-10 alkylamino, C3-C30 cycloalkyl, C1-C30 alkylthio, C6-C30 aryl, C3-C30 heteroaryl, cyano-substituted C1-C10 alkyl, C6-C30 aryl, and C3-C30 heteroaryl.
[0037] Preferably, the narrow spectrum pure green light organic electroluminescent compound has the structure shown below:
[0038]
[0039] Wherein, the definitions of Ar1, Ar2, Ar3, Ar6, Ar7, and X1-X4 are the same as those in claim 3;
[0040] Preferably, Ar1 is selected from one of the following rings:
[0041]
[0042] R1 is selected from any one of H, D, F, Cl, Br, I, benzyl, ester, amide, carbonyl, aldehyde, carbonyl, nitro, C1-C10 alkyl, C1-10 alkoxy, C1-10 alkylamino, C3-C30 cycloalkyl, C1-C30 alkylthio, C6-C30 aryl, C3-C30 heteroaryl, cyano-substituted C1-C10 alkyl, C6-C30 aryl, and C3-C30 heteroaryl.
[0043] Preferably, Ar2 is a substituted or unsubstituted C5-C20 aryl ring, or a substituted or unsubstituted C3-C20 aryl heterocyclic ring; wherein the substituents in the substituted C5-C20 aryl ring and the substituted C3-C20 aryl ring are selected from H, D, F, Cl, Br, I, nitrile, acyl, alkoxy, C1-C30 alkyl, C3-C30 cycloalkyl, C1-C30 alkylthio, C6-C30 aryl, C3-C30 heteroaryl;
[0044] Preferably, Ar2 is selected from one of the following rings:
[0045]
[0046] R1 and R2 are each independently selected from any one of H, D, F, Cl, Br, I, benzyl, ester group, amide group, carbonyl group, aldehyde group, carbonyl group, nitro group, C1-C10 alkyl group, C1-10 alkoxy group, C1-10 alkylamino group, C3-C30 cycloalkyl group, C1-C30 alkylthio group, C6-C30 aryl group, C3-C30 heteroaryl group, cyano-substituted C1-C10 alkyl group, C6-C30 aryl group, C3-C30 heteroaryl group;
[0047] Preferably, R1 and R2 are each independently selected from phenyl, methyl, and perdeuterated phenyl;
[0048] It can be understood that the perdeuterated phenyl group means that all the substitutable positions on the phenyl group are substituted with deuterium;
[0049] Preferably, Ar4 is a substituted or unsubstituted C5-C20 aryl ring, or a substituted or unsubstituted C3-C20 aryl heterocyclic ring; wherein the substituents in the substituted C5-C20 aryl ring and the substituted C3-C20 aryl ring are selected from H, D, F, Cl, Br, I, nitrile, acyl, alkoxy, C1-C30 alkyl, C3-C30 cycloalkyl, C1-C30 alkylthio, C6-C30 aryl, C3-C30 heteroaryl;
[0050] Preferably, Ar4 is selected from one of the following rings:
[0051]
[0052] R1 and R2 are each independently selected from any one of H, D, F, Cl, Br, I, benzyl, ester group, amide group, carbonyl group, aldehyde group, carbonyl group, nitro group, C1-C10 alkyl group, C1-10 alkoxy group, C1-10 alkylamino group, C3-C30 cycloalkyl group, C1-C30 alkylthio group, C6-C30 aryl group, C3-C30 heteroaryl group, cyano-substituted C1-C10 alkyl group, C6-C30 aryl group, C3-C30 heteroaryl group;
[0053] Preferably, Ar3 is selected from a substituted or unsubstituted C7-C20 fused aromatic ring, or a substituted or unsubstituted C3-C20 aryl heterocyclic ring; wherein the substituents in the substituted C7-C20 aryl ring and the substituted C3-C20 aryl heterocyclic ring are selected from H, D, F, Cl, Br, I, nitrile, acyl, alkoxy, C1-C30 alkyl, C3-C30 cycloalkyl, C1-C30 alkylthio, C6-C30 aryl, C3-C30 heteroaryl;
[0054] Preferably, Ar3 is selected from one of the following rings:
[0055]
[0056]
[0057] R1 and R2 are each independently selected from any one of H, D, F, Cl, Br, I, benzyl, ester group, amide group, carbonyl group, aldehyde group, carbonyl group, nitro group, C1-C10 alkyl group, C1-10 alkoxy group, C1-10 alkylamino group, C3-C30 cycloalkyl group, C1-C30 alkylthio group, C6-C30 aryl group, C3-C30 heteroaryl group, cyano-substituted C1-C10 alkyl group, C6-C30 aryl group, C3-C30 heteroaryl group;
[0058] Preferably, Ar5 is independently selected from a substituted or unsubstituted C7-C20 aryl ring, or a substituted or unsubstituted C3-C20 aryl heterocyclic ring; wherein the substituents in the substituted C7-C20 aryl ring and the substituted C3-C20 aryl heterocyclic ring are selected from H, D, F, Cl, Br, I, nitrile, acyl, alkoxy, C1-C30 alkyl, C3-C30 cycloalkyl, C1-C30 alkylthio, C6-C30 aryl, C3-C30 heteroaryl;
[0059] Preferably, Ar5 is selected from one of the following rings:
[0060]
[0061] R1 and R2 are each independently selected from any one of H, D, F, Cl, Br, I, benzyl, ester group, amide group, carbonyl group, aldehyde group, carbonyl group, nitro group, C1-C10 alkyl group, C1-10 alkoxy group, C1-10 alkylamino group, C3-C30 cycloalkyl group, C1-C30 alkylthio group, C6-C30 aryl group, C3-C30 heteroaryl group, cyano-substituted C1-C10 alkyl group, C6-C30 aryl group, C3-C30 heteroaryl group;
[0062] Preferably, X1 and X2 are each independently selected from -O-, -S-, -Se- or -N(R1)-; R1 is selected from substituted or unsubstituted phenyl; wherein the substituent of the substituted phenyl is selected from methyl or tert-butyl;
[0063] Preferably, X3 and X4 are each independently selected from -O-, -S-, -Se- or -N(R1)-; R1 is selected from substituted or unsubstituted phenyl; wherein the substituent of the substituted phenyl is selected from methyl or tert-butyl.
[0064] Preferably, the structure of the narrow spectrum pure green light organic electroluminescent compound is selected from any one of the following structures:
[0065]
[0066]
[0067]
[0068]
[0069]
[0070]
[0071]
[0072]
[0073]
[0074] Preferably, the sensitizer containing sulfur or selenium atoms is selected from a thermally activated delayed fluorescence sensitizer compound, and the reverse intersystem crossing rate k of the thermally activated delayed fluorescence sensitizer compound is RISC >10 5 s -1 :
[0075] Preferably, the structure of the thermally activated delayed fluorescence sensitizer compound is selected from one of the following structures:
[0076]
[0077]
[0078]
[0079] Preferably, the composition further comprises a host material, and the host material is selected from a single host material or a radical-excited composite host material; preferably, the single host material is selected from one of the following materials:
[0080]
[0081] Preferably, the radical-excited composite host material is selected from:
[0082] A combination of combination of;
[0083] Preferably, the mass ratio of the narrow spectrum pure green light organic electroluminescent compound and the sensitizer containing sulfur or selenium atoms in the narrow spectrum pure green light electroluminescent device light-emitting layer composition is (1-5): (10-30);
[0084] Preferably, the mass ratio of the narrow spectrum pure green light organic electroluminescent compound, the sensitizer containing sulfur or selenium atoms, and the host material in the narrow spectrum pure green light electroluminescent device light-emitting layer composition is x:y:(100-xy), wherein x=1-5, y=10-30.
[0085] Optionally, the mass ratio of compound 1 to compound 2 in the radical-excited composite host material is (0.8-1.2): (0.8-1.2);
[0086] Optionally, the mass ratio of compound 3 to compound 4 in the radical-excited composite host material is (0.8-1.2): (0.8-1.2).
[0087] The present invention also provides an organic electroluminescent device, which comprises an anode, a cathode and an organic layer located between the anode and the cathode, wherein the organic layer comprises a light-emitting layer, and the material of the light-emitting layer comprises the above-mentioned narrow-spectrum pure green light electroluminescent device light-emitting layer composition.
[0088] Optionally, the organic layer includes a substrate, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
[0089] Beneficial effects of the present invention:
[0090] The invention provides a narrow spectrum pure green light electroluminescent device luminescent layer composition, comprising a narrow spectrum pure green light organic electroluminescent compound and a sensitizer containing sulfur or selenium atoms; the narrow spectrum pure green light organic electroluminescent compound and the sensitizer containing sulfur or selenium atoms are used in combination to enable the electroluminescent device to emit narrow spectrum, high purity pure green light, and have a higher device external quantum efficiency and a longer lifespan;
[0091] Furthermore, the narrow-spectrum pure green light organic electroluminescent compound provided by the present invention has a structure shown in formula (1) and limits the range of its substituents, so that the compound has a higher photoluminescence quantum yield and can emit narrow-spectrum, high-purity pure green light.
[0092] Furthermore, the invention provides a narrow spectrum pure green light organic electroluminescent compound in the narrow spectrum pure green light electroluminescent device light-emitting layer composition, which has a simple and easy preparation process, and the raw materials are easily available, and is suitable for mass production and expansion. BRIEF DESCRIPTION OF THE DRAWINGS
[0093] In order to more clearly illustrate the specific implementation methods of the present invention or the technical solutions in the prior art, the drawings required for use in the specific implementation methods or the description of the prior art will be briefly introduced below. Obviously, the drawings described below are some implementation methods of the present invention. For ordinary technicians in this field, other drawings can be obtained based on these drawings without paying creative work.
[0094] Figure 1 This is a structural diagram of an organic electroluminescent device in an embodiment of the device of the present invention:
[0095] 1-substrate; 2-anode; 3-hole injection layer; 4-hole transport layer; 5-electron blocking layer; 6-luminescent layer; 7-hole blocking layer; 8-electron transport layer; 9-electron injection layer; 10-cathode;
[0096] Figure 2 The emission spectra of device example 1, device comparative example 1, and device comparative example 2 of the present invention;
[0097] Figure 3 This is a relationship diagram between the maximum external quantum efficiency and light intensity of device embodiment 1, device comparative example 1, and device comparative example 2 of the present invention. DETAILED DESCRIPTION
[0098] The following examples are provided for a better understanding of the present invention, and are not limited to the best embodiment, and do not limit the content and protection scope of the present invention. Any product identical or similar to the present invention obtained by anyone under the enlightenment of the present invention or by combining the features of the present invention with other prior arts falls within the protection scope of the present invention. For example, the synthesis of the non-exemplified compounds according to the present application can be successfully completed by a person skilled in the art through modification methods, such as appropriate protection of interfering groups, by using other known reagents in addition to those described in the present application, or making some conventional modifications to the reaction conditions, all of which fall within the protection scope of the present invention.
[0099] If no specific experimental steps or conditions are specified in the examples, the conventional experimental steps or conditions described in the literature in the field can be used. If no manufacturer is specified for the reagents or instruments used, they are all conventional reagent products that can be obtained commercially.
[0100] The specific synthesis method and device preparation method of the novel compound of the present invention will be described in detail below by taking a number of embodiments as examples, but the preparation method of the present invention is not limited to these embodiments.
[0101] The sensitizer containing sulfur or selenium atoms used in the present invention is prepared according to the description in the following document:
[0102] [1] Nat. Commun. 2014, 5, 4016
[0103] [2] Nat. Photon., 2020, 14, 636
[0104] [3]Nat.Photon.2022.16,803
[0105] [4]Chem.Eng.J.2023,482,149150
[0106] [5]Angew.Chem.Int.Ed.2023,62,e202302478
[0107] [6] Adv. Mater. 2024, 2313602
[0108] Various chemicals used in the present invention, such as petroleum ether, dichloromethane, ethyl acetate, methanol, ethanol, toluene, o-dichlorobenzene, boron tribromide, N,N-diisopropylethylamine, palladium acetate, tris(dibenzylideneacetone)dipalladium, tri-tert-butylphosphine tetrafluoroborate, sodium tert-butoxide, potassium carbonate, sodium sulfate, reaction intermediates and other basic chemical raw materials are purchased from Shanghai Bid Pharmaceutical Technology Co., Ltd. or San Chemical Technology (Shanghai) Co., Ltd. The mass spectrometer used to determine the following compounds is a LCMS-IT-TOF mass spectrometer (manufactured by Shimadzu Corporation, Japan).
[0109] The following is a brief description of the synthesis method of the light-emitting layer composition of the narrow spectrum pure green light electroluminescent device of the present invention, as shown in process (1):
[0110]
[0111] The specific process includes:
[0112] Under nitrogen atmosphere, boron tribromide (4.0-8.0 mmol) was slowly added to the o-dichlorobenzene solution of the boronated precursor (1.0 mmol), and then the reaction mixture was heated to 200°C for 24-48 hours. After the reaction was completed, it was cooled to 0°C, and N,N-diisopropylethylamine (8.0-16.0 mmol) was slowly added. After stirring at room temperature for 0.5 hours, it was extracted with dichloromethane, and the combined organic phase was dried over anhydrous sodium sulfate, filtered, and the solvent was removed under reduced pressure. The crude product was separated by silica gel column chromatography (developing solvent: petroleum ether / dichloromethane) to obtain the corresponding product. The target compound was identified by LCMS-IT-TOF mass spectrometry.
[0113] Synthesis Example
[0114] Synthesis example 1
[0115] This synthesis example provides a method for preparing a narrow-spectrum pure green light organic electroluminescent compound 1, which specifically comprises the following steps:
[0116]
[0117] Preparation of compound 1-1:
[0118] 3-Bromo-N-phenylcarbazole (10.0 mmol), 2,4,6-trimethylaniline (12.0 mmol), Pd2(dba)3 (0.5 mmol), tBu3 HBF4 (1.5 mmol), tBuONa (20.0 mmol) and toluene were added to a dry round-bottom flask equipped with a magnetic stirrer. The system was reacted at 100°C for 12 hours in a nitrogen atmosphere. After cooling to room temperature, the solvent was removed under reduced pressure, and the residue was dissolved in dichloromethane, filtered under reduced pressure through diatomaceous earth, and washed with dichloromethane. The combined filtrate was concentrated under reduced pressure and separated by silica gel column chromatography (developing solvent: petroleum ether / dichloromethane) to obtain compound 1-1 as a white solid with a yield of 89%.
[0119] Preparation of compound 1-2:
[0120] Compound 1-1 (8.2 mmol), 3,5-dibromobiphenyl (4.0 mmol), Pd2(dba)3 (0.2 mmol), tBu3 HBF4 (0.6 mmol), tBuONa (16.0 mmol) and toluene were added to a dry round-bottom flask equipped with a magnetic stirrer. The system was reacted at 100°C for 12 hours in a nitrogen atmosphere. After cooling to room temperature, the solvent was removed under reduced pressure, and the residue was dissolved in dichloromethane, filtered under reduced pressure through diatomaceous earth, and washed with dichloromethane. The combined filtrate was concentrated under reduced pressure and separated by silica gel column chromatography (developing solvent: petroleum ether / dichloromethane) to obtain compound 1-2 as a white solid with a yield of 71%.
[0121] Preparation of narrow spectrum pure green light organic electroluminescent compound 1:
[0122] Under a nitrogen atmosphere, boron tribromide (4.0 mmol) was slowly added to a solution of compound 1-2 (1.0 mmol) in o-dichlorobenzene, and then the reaction mixture was heated to 200°C for 24 hours. After the reaction was completed, it was cooled to 0°C, N,N-diisopropylethylamine (8.0 mmol) was slowly added, and after stirring at room temperature for 0.5 hours, it was extracted with dichloromethane, and the combined organic phase was dried over anhydrous sodium sulfate, filtered, and the solvent was removed under reduced pressure. The crude product was separated by silica gel column chromatography (developing agent: petroleum ether / dichloromethane) to obtain a narrow spectrum pure green light organic electroluminescent compound 1, a bright yellow solid, with a yield of 83%. The target compound was identified by LCMS-IT-TOF mass spectrometry. HRMS (ESI + ):calcd for C 66 H 52 BN4 + [M+H] + 911.4280; found 911.4289.
[0123] Synthesis example 2
[0124] This synthesis example provides a method for preparing a narrow-spectrum pure green light organic electroluminescent compound 2, which specifically comprises the following steps:
[0125]
[0126] The preparation method of compound 2-2 in this synthesis example is similar to the preparation method of compound 1-2 in synthesis example 1, except that when synthesizing compound 2-2, 3,5-dibromobiphenyl needs to be replaced with an equal amount of 1,3-dibromo-5-chlorobenzene;
[0127] Preparation of compound 2-3
[0128] Compound 2-2 (4 mmol), 4-dibenzofuran boronic acid (4.4 mmol), Pd(PPh3)4 (0.2 mmol), K2CO3 (8.0 mmol) and toluene / ethanol / water (3 / 1 / 1, v / v / v) were added to a dry round-bottom flask equipped with a magnetic stirrer. The system was reacted at 90°C for 12 hours in a nitrogen atmosphere. After cooling to room temperature, the solvent was removed under reduced pressure, and the residue was dissolved in dichloromethane, filtered under reduced pressure through diatomaceous earth, and washed with dichloromethane. The combined filtrate was concentrated under reduced pressure and separated by silica gel column chromatography (developing solvent: petroleum ether / dichloromethane) to obtain compound 2-3 as a white solid with a yield of 87%;
[0129] Preparation of narrow spectrum pure green light organic electroluminescent compound 2:
[0130] The preparation method is basically the same as that of the narrow spectrum pure green light organic electroluminescent compound 1, except that compound 1-2 is replaced by an equal amount of compound 2-3. The crude product is separated by silica gel column chromatography (developing solvent: petroleum ether / dichloromethane) to obtain a narrow spectrum pure green light organic electroluminescent compound 2, a bright yellow solid, with a yield of 86%. The target compound is identified by LCMS-IT-TOF mass spectrometry. HRMS (ESI + ):calcd for C 72 H 54 BN4O + [M+H] + 1001.4385; found 1001.4390.
[0131] Synthesis example 3
[0132] This synthesis example provides a method for preparing a narrow spectrum pure green light organic electroluminescent compound 3, which specifically comprises the following steps:
[0133]
[0134] Preparation of compound 3-1:
[0135] 1,3-dibromobenzene (10.0mmol), 2,4,6-trimethylaniline (22.0mmol), Pd2(dba)3 (0.5mmol), tBu3 HBF4 (1.5mmol), tBuONa (40.0mmol) and toluene were added to a dry round-bottom flask equipped with a magnetic stirrer. The system was reacted at 100°C for 12 hours in a nitrogen atmosphere. After cooling to room temperature, the solvent was removed under reduced pressure, and the residue was dissolved in dichloromethane, filtered under reduced pressure through diatomaceous earth, and washed with dichloromethane. The combined filtrate was concentrated under reduced pressure and separated by silica gel column chromatography (developing solvent: petroleum ether / dichloromethane) to obtain compound 3-1 as a white solid with a yield of 94%.
[0136] Preparation of compound 3-2:
[0137] Compound 3-1 (9.0 mmol), 2-bromonaphthalene (8.8 mmol), Pd(OAc)2 (0.5 mmol), dppf (1.5 mmol), tBuONa (13.5 mmol) and toluene were added to a dry round-bottom flask equipped with a magnetic stirrer. The system was reacted at 90°C for 4 hours in a nitrogen atmosphere. After cooling to room temperature, the solvent was removed under reduced pressure, and the residue was dissolved in dichloromethane, filtered under reduced pressure through diatomaceous earth, and washed with dichloromethane. The combined filtrate was concentrated under reduced pressure and separated by silica gel column chromatography (developing solvent: petroleum ether / dichloromethane) to obtain compound 3-2 as a white solid with a yield of 64%.
[0138] Preparation of compound 3-3:
[0139] The preparation method is basically the same as that of compound 1-2, except that compound 1-1 is replaced by an equal amount of compound 3-2. Compound 3-3 is obtained by silica gel column chromatography (developing solvent: petroleum ether / dichloromethane) as a white solid with a yield of 75%.
[0140] Preparation of narrow spectrum pure green light organic electroluminescent compound 3:
[0141] Under a nitrogen atmosphere, boron tribromide (6.0 mmol) was slowly added to a solution of compound 3-3 (1.0 mmol) in o-dichlorobenzene, and then the reaction mixture was heated to 200°C for 48 hours. After the reaction was completed, it was cooled to 0°C, N,N-diisopropylethylamine (12.0 mmol) was slowly added, and after stirring at room temperature for 0.5 hours, it was extracted with dichloromethane, and the combined organic phase was dried over anhydrous sodium sulfate, filtered, and the solvent was removed under reduced pressure. The crude product was separated by silica gel column chromatography (developing agent: petroleum ether / dichloromethane) to obtain a narrow spectrum pure green light organic electroluminescent compound 3, a bright yellow solid, with a yield of 80%. The target compound was identified by LCMS-IT-TOF mass spectrometry. HRMS (ESI + ):calcd for C74 H 65 B2N4 + [M+H] + 1031.5390; found 1031.5400.
[0142] Synthesis example 4
[0143] This synthesis example provides a method for preparing a narrow-spectrum pure green light organic electroluminescent compound 4, which specifically comprises the following steps:
[0144]
[0145] The preparation methods of compound 4-1, compound 4-2 and compound 4-3 are basically the same as compound 1-1.
[0146] Preparation of compound 4-4:
[0147] Compound 4-2 (5.0 mmol), compound 4-3 (5.5 mmol), Cs2CO3 (10.0 mmol) and N,N-dimethylformamide were added to a dry round-bottom flask equipped with a magnetic stirrer. The system was reacted at 150°C for 24 hours in a nitrogen atmosphere. After cooling to room temperature, the reaction system was poured into water and extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and separated by silica gel column chromatography (developing solvent: petroleum ether / dichloromethane) to obtain compound 4-4 as a white solid with a yield of 65%.
[0148] Preparation of narrow spectrum pure green light organic electroluminescent compound 4:
[0149] Under a nitrogen atmosphere, boron tribromide (8.0 mmol) was slowly added to a solution of compound 4-4 (1.0 mmol) in o-dichlorobenzene, and then the reaction mixture was heated to 200°C for 48 hours. After the reaction was completed, it was cooled to 0°C, N,N-diisopropylethylamine (12.0 mmol) was slowly added, and after stirring at room temperature for 0.5 hours, it was extracted with dichloromethane, and the combined organic phase was dried over anhydrous sodium sulfate, filtered, and the solvent was removed under reduced pressure. The crude product was separated by silica gel column chromatography (developing agent: petroleum ether / dichloromethane) to obtain a narrow spectrum pure green light organic electroluminescent compound 4, a bright yellow solid, with a yield of 76%. The target compound was identified by LCMS-IT-TOF mass spectrometry. HRMS (ESI + ):calcd for C 59 H 54 B2N3O + [M+H] + 842.4448; found 842.4452.
[0150] Device Embodiment
[0151] The present invention provides an OLED device composed of different organic electroluminescent materials, wherein the OLED device has the following layer structure (see Figure 1 ): substrate (coated glass substrate 1 with indium tin oxide (ITO) as anode 2) / hole injection layer 3 (HAT-CN) / hole transport layer 4 (TAPC and TCTA) / electron blocking layer 5 (mCBP) / light-emitting layer 6 (EML) / hole blocking layer 7 (POT2T) / electron transport layer 8 (ANT-BIZ) / electron injection layer 9 (Liq) / cathode 10 (Al).
[0152] The materials used in the OLED device are as follows:
[0153]
[0154] The preparation of device examples 1-10 and device comparative examples 1-2 includes the following steps:
[0155] 1. Cleaning of indium tin oxide (ITO) glass: wash with ethanol and acetone in sequence, blow off the surface solvent with nitrogen gas flow, and then treat in a plasma cleaner for 10 minutes;
[0156] 2. Evaporation at 2.0×10 -4 The process is carried out in a high vacuum chamber below Pa, which is placed in an inert gas glove box, and the evaporation rate is 0.1 nm / s;
[0157] 3. On the anode ITO glass, a hole injection layer (material is HAT-CN, thickness is 5nm), a hole transport layer (the hole transport layer includes a TAPC material layer (the TAPC material layer has a thickness of 30nm and is adjacent to the hole injection layer), a TCTA material layer (the TCTA material layer has a thickness of 15nm and is adjacent to the TAPC material layer)) and an electron blocking layer (material is mCBP, thickness is 10nm) are vacuum evaporated in sequence; on the electron blocking layer, a co-evaporated light layer (thickness is 45nm, the specific materials are shown in Table 1) is vacuum evaporated; on the light-emitting layer, a hole blocking layer (material is POT2T, thickness is 20nm), an electron transport layer (material is ANT-BIZ, thickness is 30nm), an electron injection layer (material is Liq, thickness is 2nm) and a cathode Al (100nm) are vacuum evaporated.
[0158] The mass ratios of the narrow spectrum pure green light organic electroluminescent compound, the thermally activated delayed fluorescence sensitizer compound, and the main material in the light-emitting layer of the device are shown in Table 1; wherein the mass ratio of compound 1 and compound 2 in the main material in device embodiment 4, device embodiment 7, and device embodiment 9 is 1:1; and the mass ratio of compound 3 and compound 4 in device embodiment 10 is 1:1.
[0159] Table 1
[0160]
[0161] The narrow spectrum pure green light organic electroluminescent compound, thermally activated delayed fluorescence sensitizer compound and main body material in the light-emitting layer of the device are specifically shown in Table 2;
[0162] Table 2
[0163]
[0164]
[0165]
[0166] Device Test Case
[0167] The organic electroluminescent devices obtained from device examples 1-10 and comparative examples 1-2 in the device examples were tested.
[0168] The EQE-brightness curves and electroluminescence spectra were collected using Keithley 2400 and an absolute EQE measurement system (C9920-12, Hamamatsu Photonics, Japan). The device operating life (LT50, LT50 refers to the time taken for the brightness to decay to 50% of the initial brightness) was evaluated by measuring the brightness over time at a constant current density. Figure 2 The emission spectra of device example 1, device comparative example 1, and device comparative example 2 of the present invention; Figure 3 This is a graph showing the relationship between the maximum external quantum efficiency and light intensity of device Example 1, device Comparative Example 1, and device Comparative Example 2 of the present invention;
[0169] The device performance test results are shown in Table 3 and Table 4:
[0170] Table 3
[0171]
[0172]
[0173] Table 4
[0174]
[0175] Table 3 Data Notes: [a] EL peak : Brightness is 1000cd / m 2 [b] fluorescence emission peak at ; [b] emission half-peak width; [c] chromaticity coordinates of the device’s luminescence spectrum.
[0176] Table 4 Data Notes: [d] Maximum external quantum efficiency; [e] Initial brightness is 1000 cd / m 2The half-life of the device.
[0177] Obviously, the above embodiments are merely examples for the purpose of clear explanation, and are not intended to limit the implementation methods. For those skilled in the art, other different forms of changes or modifications can be made based on the above description. It is not necessary and impossible to list all the implementation methods here. The obvious changes or modifications derived therefrom are still within the scope of protection of the invention.
Claims
1. A narrow spectrum pure green light electroluminescent device light-emitting layer composition, characterized in that: It includes narrow spectrum pure green light organic electroluminescent compounds and sensitizers containing sulfur or selenium atoms.
2. The narrow spectrum pure green light electroluminescent device light-emitting layer composition according to claim 1, characterized in that: The narrow spectrum pure green light organic electroluminescent compound has the structure shown below: Wherein, Ar1 is a substituted or unsubstituted C5-C10 aryl ring, or a substituted or unsubstituted C3-C6 aryl heterocycle; Ar2 is a substituted or unsubstituted C5-C60 aryl ring, or a substituted or unsubstituted C3-C60 aryl heterocycle; Ar3 is a substituted or unsubstituted C7-C60 fused aromatic ring, or a substituted or unsubstituted C3-C60 aromatic heterocyclic ring; Ar4 is absent, or is a substituted or unsubstituted C5-C60 aryl ring, or a substituted or unsubstituted C3-C80 aryl heterocycle; X1 and X2 are each independently selected from -O-, -S-, -Se- or -N(R1)-; R1 is selected from any one of H, D, F, Cl, Br, I, benzyl, ester group, amide group, carbonyl group, aldehyde group, carbonyl group, nitro group, C1-C10 alkyl group, C1-10 alkoxy group, C1-10 alkylamino group, C3-C30 cycloalkyl group, C1-C30 alkylthio group, C6-C30 aryl group, C3-C30 heteroaryl group, cyano-substituted C1-C10 alkyl group, C6-C30 aryl group, C3-C30 heteroaryl group; Among them, the substituents in the substituted C5-C10 aryl ring, substituted C3-C6 aryl heterocycle, substituted C7-C60 condensed aromatic ring, substituted C5-C60 aryl ring, substituted C3-C60 aryl heterocycle, and substituted C3-C80 aryl heterocycle are selected from H, D, F, Cl, Br, I, nitrile, acyl, alkoxy, C1-C30 alkyl, C3-C30 cycloalkyl, C1-C30 alkylthio, C6-C30 aryl, and C3-C30 heteroaryl.
3. The narrow spectrum pure green light electroluminescent device light emitting layer composition according to claim 1 or 2, characterized in that: The narrow spectrum pure green light organic electroluminescent compound has the following structure: Wherein, Ar5 is a substituted or unsubstituted C7-C60 aryl ring, or a substituted or unsubstituted C3-C60 aryl heterocycle; The substituents in the substituted C7-C60 aryl ring and the substituted C5-C60 aryl ring are selected from H, D, F, Cl, Br, I, nitrile, acyl, alkoxy, C1-C30 alkyl, C3-C30 cycloalkyl, C1-C30 alkylthio, C6-C30 aryl, and C3-C30 heteroaryl; The definitions of Ar2, Ar3, X1, and X2 are the same as those in claim 1.
4. The narrow spectrum pure green light electroluminescent device light-emitting layer composition according to any one of claims 1 to 3, characterized in that: The structure of Ar4 is as shown in the following formula (3): Wherein, Ar5 is a substituted or unsubstituted C5-C60 aryl ring, or a substituted or unsubstituted C3-C60 aryl heterocycle; Ar6 is a substituted or unsubstituted C7-C60 aryl ring, or a substituted or unsubstituted C3-C60 aryl heterocycle; Ar4 is absent, or is a substituted or unsubstituted C5-C60 aryl ring, or a substituted or unsubstituted C3-C80 aryl heterocycle; X3 and X4 are each independently selected from -O-, -S-, -Se- or -N(R1)-; R1 is selected from any one of H, D, F, Cl, Br, I, benzyl, ester, amide, carbonyl, aldehyde, carbonyl, nitro, C1-C10 alkyl, C1-10 alkoxy, C1-10 alkylamino, C3-C30 cycloalkyl, C1-C30 alkylthio, C6-C30 aryl, C3-C30 heteroaryl, cyano-substituted C1-C10 alkyl, C6-C30 aryl, and C3-C30 heteroaryl.
5. The narrow spectrum pure green light electroluminescent device light emitting layer composition according to any one of claims 1 to 4, characterized in that: The narrow spectrum pure green light organic electroluminescent compound has the following structure: Wherein, the definitions of Ar1, Ar2, Ar3, Ar6, Ar7, and X1-X4 are the same as those in claim 4.
6. The narrow spectrum pure green light electroluminescent device light emitting layer composition according to any one of claims 1 to 5, characterized in that: Ar1 is selected from one of the following rings: R1 is selected from any one of H, D, F, Cl, Br, I, benzyl, ester, amide, carbonyl, aldehyde, carbonyl, nitro, C1-C10 alkyl, C1-10 alkoxy, C1-10 alkylamino, C3-C30 cycloalkyl, C1-C30 alkylthio, C6-C30 aryl, C3-C30 heteroaryl, cyano-substituted C1-C10 alkyl, C6-C30 aryl, and C3-C30 heteroaryl.
7. The narrow spectrum pure green light electroluminescent device light emitting layer composition according to any one of claims 1 to 6, characterized in that: Ar2 is a substituted or unsubstituted C5-C20 aryl ring, or a substituted or unsubstituted C3-C20 aryl heterocyclic ring; wherein the substituents in the substituted C5-C20 aryl ring and the substituted C3-C20 aryl ring are selected from H, D, F, Cl, Br, I, nitrile, acyl, alkoxy, C1-C30 alkyl, C3-C30 cycloalkyl, C1-C30 alkylthio, C6-C30 aryl, and C3-C30 heteroaryl; Preferably, Ar2 is selected from one of the following rings: R1 and R2 are each independently selected from any one of H, D, F, Cl, Br, I, benzyl, ester group, amide group, carbonyl group, aldehyde group, carbonyl group, nitro group, C1-C10 alkyl group, C1-10 alkoxy group, C1-10 alkylamino group, C3-C30 cycloalkyl group, C1-C30 alkylthio group, C6-C30 aryl group, C3-C30 heteroaryl group, cyano-substituted C1-C10 alkyl group, C6-C30 aryl group, C3-C30 heteroaryl group; Preferably, Ar4 is a substituted or unsubstituted C5-C20 aryl ring, or a substituted or unsubstituted C3-C20 aryl heterocyclic ring; wherein the substituents in the substituted C5-C20 aryl ring and the substituted C3-C20 aryl ring are selected from H, D, F, Cl, Br, I, nitrile, acyl, alkoxy, C1-C30 alkyl, C3-C30 cycloalkyl, C1-C30 alkylthio, C6-C30 aryl, C3-C30 heteroaryl; Preferably, Ar4 is selected from one of the following rings: R1 and R2 are each independently selected from any one of H, D, F, Cl, Br, I, benzyl, ester group, amide group, carbonyl group, aldehyde group, carbonyl group, nitro group, C1-C10 alkyl group, C1-10 alkoxy group, C1-10 alkylamino group, C3-C30 cycloalkyl group, C1-C30 alkylthio group, C6-C30 aryl group, C3-C30 heteroaryl group, cyano-substituted C1-C10 alkyl group, C6-C30 aryl group, C3-C30 heteroaryl group; Preferably, Ar3 is selected from a substituted or unsubstituted C7-C20 fused aromatic ring, or a substituted or unsubstituted C3-C20 aryl heterocyclic ring; wherein the substituents in the substituted C7-C20 aryl ring and the substituted C3-C20 aryl heterocyclic ring are selected from H, D, F, Cl, Br, I, nitrile, acyl, alkoxy, C1-C30 alkyl, C3-C30 cycloalkyl, C1-C30 alkylthio, C6-C30 aryl, C3-C30 heteroaryl; Preferably, Ar3 is selected from one of the following rings: R1 and R2 are each independently selected from any one of H, D, F, Cl, Br, I, benzyl, ester group, amide group, carbonyl group, aldehyde group, carbonyl group, nitro group, C1-C10 alkyl group, C1-10 alkoxy group, C1-10 alkylamino group, C3-C30 cycloalkyl group, C1-C30 alkylthio group, C6-C30 aryl group, C3-C30 heteroaryl group, cyano-substituted C1-C10 alkyl group, C6-C30 aryl group, C3-C30 heteroaryl group; Preferably, Ar5 is independently selected from a substituted or unsubstituted C7-C20 aryl ring, or a substituted or unsubstituted C3-C20 aryl heterocyclic ring; wherein the substituents in the substituted C7-C20 aryl ring and the substituted C3-C20 aryl heterocyclic ring are selected from H, D, F, Cl, Br, I, nitrile, acyl, alkoxy, C1-C30 alkyl, C3-C30 cycloalkyl, C1-C30 alkylthio, C6-C30 aryl, C3-C30 heteroaryl; Preferably, Ar5 is selected from one of the following rings: R1 and R2 are each independently selected from any one of H, D, F, Cl, Br, I, benzyl, ester group, amide group, carbonyl group, aldehyde group, carbonyl group, nitro group, C1-C10 alkyl group, C1-10 alkoxy group, C1-10 alkylamino group, C3-C30 cycloalkyl group, C1-C30 alkylthio group, C6-C30 aryl group, C3-C30 heteroaryl group, cyano-substituted C1-C10 alkyl group, C6-C30 aryl group, C3-C30 heteroaryl group; Preferably, X1 and X2 are each independently selected from -O-, -S-, -Se- or -N(R1)-; R1 is selected from substituted or unsubstituted phenyl; wherein the substituent of the substituted phenyl is selected from methyl or tert-butyl; Preferably, X3 and X4 are each independently selected from -O-, -S-, -Se- or -N(R1)-; R1 is selected from substituted or unsubstituted phenyl; wherein the substituent of the substituted phenyl is selected from methyl or tert-butyl.
8. The composition for the light-emitting layer of a narrow spectrum pure green electroluminescent device according to any one of claims 1 to 7, characterized in that: The structure of the narrow spectrum pure green light organic electroluminescent compound is selected from any one of the following structures:
9. The narrow spectrum pure green light electroluminescent device light emitting layer composition according to any one of claims 1 to 8, characterized in that: The sensitizer containing sulfur or selenium atoms is selected from a thermally activated delayed fluorescence sensitizer compound, and the reverse intersystem crossing rate k of the thermally activated delayed fluorescence sensitizer compound is RISC >10 5 s -1 ; Preferably, the structure of the thermally activated delayed fluorescence sensitizer compound is selected from one of the following structures: Preferably, the composition further comprises a host material, and the host material is selected from a single host material or a radical-excited composite host material; preferably, the single host material is selected from one of the following materials: Preferably, the radical-excited composite host material is selected from: A combination of combination of; Preferably, the mass ratio of the narrow spectrum pure green light organic electroluminescent compound and the sensitizer containing sulfur or selenium atoms in the narrow spectrum pure green light electroluminescent device light-emitting layer composition is (1-5): (10-30); Preferably, the mass ratio of the narrow spectrum pure green light organic electroluminescent compound, the sensitizer containing sulfur or selenium atoms, and the host material in the narrow spectrum pure green light electroluminescent device light-emitting layer composition is x:y:(100-xy), wherein x=1-5, y=10-30.
10. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises an anode, a cathode and an organic layer between the anode and the cathode, the organic layer comprises a light-emitting layer, and the material of the light-emitting layer comprises the narrow-spectrum pure green light electroluminescent device light-emitting layer composition according to any one of claims 1-9.
