CN106883240A - Three s-triazines and luminescent device - Google Patents

Three s-triazines and luminescent device Download PDF

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CN106883240A
CN106883240A CN201710044808.3A CN201710044808A CN106883240A CN 106883240 A CN106883240 A CN 106883240A CN 201710044808 A CN201710044808 A CN 201710044808A CN 106883240 A CN106883240 A CN 106883240A
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黄达
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ACC Acoustic Technologies Shenzhen Co Ltd
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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Abstract

The present invention discloses a kind of three s-triazine.Three s-triazine maintains D π A structures, maintains the performance of TADF；And substituted radical contains fragrance or aromatic heterocycle structure, glass transition temperature is high, and heat resistance is good；Substituted radical is different, and molecule has unsymmetric structure, it is not easy to crystallize, good film-forming property.The present invention also provides a kind of luminescent device of application three s-triazine.

Description

Tri-s-triazine compound and light-emitting device
[ technical field ] A method for producing a semiconductor device
The invention relates to the technical field of organic luminescent materials, in particular to a tris-s-triazine compound and a luminescent device using the tris-s-triazine compound.
[ background of the invention ]
The use of Organic Light Emitting Diodes (OLEDs) for large area flat panel displays and lighting has attracted considerable attention in the industry and academia. However, the conventional organic fluorescent material can emit light only by using 25% singlet excitons formed by electric excitation, and the internal quantum efficiency of the device is low (up to 25%). Although the phosphorescence material enhances the intersystem crossing due to the strong spin-orbit coupling of the atomic center, the singlet state excitons and the triplet state excitons formed by the electric excitation can be effectively used for emitting light, so that the internal quantum efficiency of the device reaches 100 percent. However, the application of phosphorescent materials in OLEDs is limited by the problems of high price, poor material stability, serious device efficiency roll-off and the like. A Thermally Activated Delayed Fluorescence (TADF) material is a third generation organic light emitting material that has been developed following organic fluorescent materials and organic phosphorescent materials. Such materials typically have a small singlet-triplet energy level difference (Δ E)ST) The triplet excitons may be converted to singlet excitons by intersystem crossing to emit light. This can make full use of singlet excitons and triplet excitons formed under electrical excitation, and the internal quantum efficiency of the device can reach 100%. At the same time, the material structureControllable, stable in property, low in price, free of precious metal and wide in application prospect in the field of OLEDs.
Thermally Activated Delayed Fluorescence (TADF) materials have made a major breakthrough from the ada-kilo-wave research group at kyushu university, 2012, and have received great attention in the industry after the academic papers published in Nature (Nature,2012,492: 234-.
The TADF material is required to have a D-pi-A structure. Where D is an electron Donor (Donor), also known as an electron donating group, electron donors commonly used in the art are aromatic amine systems in which one of the nitrogen atoms is hybridized sp 3. The aromatic amine system refers to an aryl amine system, wherein aryl groups and aryl groups can be connected through chemical bonds such as single bonds, ether bonds and the like, the aryl groups can be aryl groups or condensed ring aryl groups with only carbon and hydrogen elements, and can also be hetero-aryl groups or condensed ring heteroaryl groups containing hetero atoms, and typical structures of the aryl groups are diphenyl amine derivatives and carbazolyl derivatives. A is an electron Acceptor (Acceptor), also called an electron-withdrawing group, and heterocyclic ring systems with carbon-nitrogen double bonds can be used as the electron Acceptor, wherein one nitrogen atom is hybridized by sp 2. The electron acceptor may be a hydrocarbon aromatic system containing no hetero atom, but has a weaker electron-withdrawing ability than a heterocyclic system having a carbon-nitrogen double bond. Pi is a bridging group which can be an aromatic conjugated system, a non-aromatic conjugated system or a single bond, as long as the Donor group and the Acceptor group can be connected in a non-conjugated way.
In terms of material application, TADF can be used not only as a material for a light-emitting layer. For example, based on TADF materials (advanced materials, adv.mater, 2012,24, 3410-.
The electron donor commonly used in the industry is an aromatic amine system, and has the advantages of easily available raw materials, easy synthesis, high thermal stability and high chemical stability. Therefore, the search for suitable electron acceptor groups that match existing electron donors is a problem that needs to be solved urgently.
The tris-triazine group has good electronegativity and thermal stability, and photoelectric properties are convenient to adjust, and chemical review (chem.Rev.,2016,116,7159-7329) reports materials with such structures in the photoelectric field, particularly in the photocatalysis field. However, no mention is made of the use of materials of this type of structure in OLEDs.
As early as 1961, patents (FR1357368A and US3089875) applied for a tris-s-triazine derivative in which both an aromatic amine group and an aliphatic amine group were introduced. In 1962, the inventors provided a method for synthesizing tris-s-triazine compounds represented by compound (a) and compound (b) in organic chemistry (j. org. chem.,1962,27, 4262-.
In 2010, chemical communication (chem. commun.,2010,46,2829-2831) re-published a synthetic method of a tris-s-triazine intermediate (formula c) based on a similar approach.
WO2010132953a1 in 2010 discloses a device using a tris-s-triazine derivative in which the trisubstituted aromatic groups of the tris-s-triazine derivative are all the same, and the tris-s-triazine derivative is used as a hole transport layer or a hole injection layer.
In 2013, the developer of TADF, the ada-thousand-wave vector, in patent WO2013133359a1, discloses a tris-s-triazine derivative used for delaying fluorescence, and the structures shown in the publication are diphenylamine derivative groups as substituent groups, as shown in formula (d) and formula (e). Tris-s-triazine derivatives with carbazole substituents are not disclosed.
In 2015, material chemistry (j. mater. chem.c,2015,3,4859-4867) provided theoretical calculations of the photoelectric properties of a series of tris-s-triazine derivatives having only one carbazole group, and typical structures are shown in formula (f) and formula (g). Through reports in the literature on the highest occupied orbital (HOMO) and the lowest unoccupied orbital (LUMO), the structure can be seen to have the basic requirements of a TADF material, and the calculation result shows that the Delta Est is about 0.5 eV. However, in addition to a carbazole group, the other linking groups are aliphatic linking groups, and the glass transition temperature is necessarily greatly affected.
Tri-s-triazine has excellent thermal stability and chemical stability, but in the field of OLED, due to the fact that the tri-s-triazine has a large planar structure, the planes are easy to interact, the performance of an amorphous film is poor, and when the tri-s-triazine is made into a light-emitting device, materials are easy to be subjected to Joule heat to generate phase separation, so that the light-emitting device is aged and deteriorated.
Therefore, there is an urgent need for a novel tris-s-triazine derivative that solves the above technical problems.
[ summary of the invention ]
The present invention aims at providing one kind of tris-s-triazine compound with high heat stability, high chemical stability and high filming performance.
The technical scheme of the invention is as follows:
a tris-s-triazine compound of the general formula:
wherein,
DA1、DA2each independently represents an electron donating group DD having a carbon number of C12-C60 or an electron withdrawing group AA having a carbon number of C12-C60;
electron donating group DD represents an organic group having at least one nitrogen atom that is sp3 hybridized;
the electron-withdrawing group AA represents an organic group having at least one nitrogen atom hybridized with sp2, or an aromatic group composed of substituted or unsubstituted hydrocarbon elements;
in the general formula (II), ring Y1、Y2、Y3Each independently represents a substituted or unsubstituted triazine ring, pyrazine ring, pyrimidine ring, pyridine ring or benzene ring.
Preferably, the electron donating group DD is selected from the group consisting of structures represented by the following general formula:
wherein R is1、R2、R3Each independently represents hydrogen, halogen, substituted or unsubstituted alkyl with carbon number of C1-C6, substituted or unsubstituted aryl with carbon number of C6-C12, or substituted or unsubstituted nitrogen-containing heteroaryl with carbon number of C6-C12; r11、R12Linked by covalent bonds and each independently representsSubstituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C12 aryl; x represents an O atom, an S atom, a sulfoxide group or a sulfone group.
Preferably, the electron donating group DD is selected from the group consisting of structures represented by the following general formula:
wherein R is4、R5、R6Each independently represents hydrogen, halogen, substituted or unsubstituted alkyl with carbon number of C1-C6, substituted or unsubstituted aryl with carbon number of C6-C12, or substituted or unsubstituted nitrogen-containing heteroaryl with carbon number of C6-12.
Preferably, the halogen is fluorine atom, chlorine atom, bromine atom, iodine atom; the substituted or unsubstituted alkyl group is methyl, ethyl, propyl, butyl, pentyl, hexyl, trifluoromethyl, pentafluoroethyl; the substituted or unsubstituted aryl is phenyl, tolyl, ethylphenyl, propylphenyl, butylphenyl, pentylphenyl, hexylphenyl, fluorophenyl, fluoro-substituted tolyl, fluoro-substituted ethylphenyl, fluoro-substituted propylphenyl, fluoro-substituted butylphenyl, fluoro-substituted pentylphenyl, fluoro-substituted hexylphenyl, naphthyl, methylnaphthyl, ethylnaphthyl, trifluoromethylnaphthyl, fluoro-substituted naphthyl, biphenyl, methylbiphenyl, dimethylbiphenyl; the substituted or unsubstituted nitrogen-containing heteroaryl group is pyridyl, pyrazinyl, pyrimidinyl, pyridyl, triazinyl, fluoro-substituted pyridyl, fluoro-substituted pyrazinyl, fluoro-substituted pyrimidinyl, fluoro-substituted pyridyl, fluoro-substituted triazinyl, trifluoromethyl-substituted pyridyl, trifluoromethyl-substituted pyrazinyl, trifluoromethyl-substituted pyrimidinyl, trifluoromethyl-substituted pyridyl, trifluoromethyl-substituted triazinyl, benzopyridyl, benzopyrazinyl, benzopyrimidinyl, benzotriazinyl, methyl-substituted benzopyridyl, methyl-substituted benzopyrazinyl, methyl-substituted benzopyrimidinyl, methyl-substituted benzotriazinyl.
Preferably, the electron withdrawing group AA has a structure represented by the following general formula:
wherein, ring Z1Represents a substituted or unsubstituted hydrocarbon aromatic ring, a hydrocarbon aromatic condensed ring, a five-membered nitrogen-containing heterocyclic ring, a six-membered nitrogen-containing heterocyclic ring, a benzo five-membered nitrogen-containing heterocyclic ring, a benzo six-membered nitrogen-containing heterocyclic ring; ring Z2、Z3Each independently represents an unsubstituted group, or a substituted or unsubstituted hydrocarbon aromatic ring, hydrocarbon aromatic condensed ring, five-membered nitrogen-containing heterocycle, six-membered nitrogen-containing heterocycle, benzo five-membered nitrogen-containing heterocycle and benzo six-membered nitrogen-containing heterocycle; ring Z1、Z2、Z3Connected by a single bond.
Preferably, said ring Z1、Z2、Z3Each independently represents a triazine ring, a pyrazine ring, a pyrimidine ring, a pyridine ring, a benzene ring, an alkyl-substituted triazine ring, an alkyl-substituted pyrazine ring, an alkyl-substituted pyrimidine ring, an alkyl-substituted pyridine ring, an alkyl-substituted benzene ring, a fluorine-substituted triazine ring, a fluorine-substituted pyrazine ring, a fluorine-substituted pyrimidine ring, a fluorine-substituted pyridine ring, a fluorine-substituted benzene ring, an indole ring, a quinoline ring, a pteridine ring, an acridine ring, an alkyl-substituted indole ring, an alkyl-substituted quinoline ring, an alkyl-substituted pteridine ring, an alkyl-substituted acridine ring, a fluorine-substituted indole ring, a fluorine-substituted quinoline ring, a fluorine-substituted pteridine ring, a fluorine-substituted acridine ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyrene ring, a perylene ring, a benzophenanthrene ring, an alkyl-substituted naphthalene ring, an alkyl-substituted anthracene ring, an alkyl-substituted phenanthrene ring, an alkyl-substituted pyrene ring, an alkyl-substituted perylene ring, an alkyl-substituted benzophenanthrene ring, A fluorine-substituted naphthalene ring, a fluorine-substituted anthracene ring, a fluorine-substituted phenanthrene ring, a fluorine-substituted pyrene ring, a fluorine-substituted perylene ring or a fluorine-substituted benzophenanthrene ring; wherein said alkyl group representsMethyl, ethyl, propyl, butyl, pentyl, hexyl, fluoro-substituted methyl, fluoro-substituted ethyl, fluoro-substituted propyl, fluoro-substituted butyl, fluoro-substituted pentyl or fluoro-substituted hexyl.
When the tris-s-triazine compound is of formula (i), it is preferably selected from the group consisting of the following structures:
when the tris-s-triazine compound is of the general formula (ii), it is preferably selected from the group consisting of the following structures:
the invention also provides a light-emitting device which comprises an anode, a cathode and a plurality of organic layers arranged between the anode and the cathode, wherein at least one of the organic layers is made of the tris-s-triazine compound.
Compared with the related art, the tris-s-triazine compound provided by the invention has the beneficial effects that:
firstly, the tris-s-triazine compound maintains a D-pi-A structure and maintains the performance of TADF; the substituent group contains an aromatic or heteroaromatic structure, so that the glass transition temperature is high, and the heat resistance is good; the substituent groups are different, the molecules have asymmetric structures, the crystallization is not easy, and the film forming property is good.
Secondly, when the tris-s-triazine compound is applied to a light-emitting device, the maximum external quantum efficiency exceeds the theoretical external quantum efficiency of a fluorescent material, and the tris-s-triazine compound provided by the invention is considered to have the performance of a TADF material.
[ description of the drawings ]
Fig. 1 is a schematic structural diagram of a light emitting device provided by the present invention.
[ detailed description ] embodiments
The invention will be further explained with reference to the drawings and the embodiments.
A tris-s-triazine compound of the general formula:
wherein,
DA1、DA2each independently represents an electron donating group DD having a carbon number of C12-C60 or an electron withdrawing group AA having a carbon number of C12-C60;
electron donating group DD represents an organic group having at least one nitrogen atom that is sp3 hybridized;
the electron-withdrawing group AA represents an organic group having at least one nitrogen atom hybridized with sp2, or an aromatic group composed of substituted or unsubstituted hydrocarbon elements;
in the general formula (II), ring Y1、Y2、Y3Each independently represents a substituted or unsubstituted triazine ring, pyrazine ring, pyrimidine ring, pyridine ring or benzene ring.
Preferably, the electron donating group DD is selected from the group consisting of structures represented by the following general formula:
wherein R is1、R2、R3Each independently represents hydrogen, halogen, substituted or unsubstituted alkyl with carbon number of C1-C6, substituted or unsubstituted aryl with carbon number of C6-C12, or substituted or unsubstituted nitrogen-containing heteroaryl with carbon number of C6-C12; r11、R12Are connected by covalent bonds and respectively and independently represent a substituted or unsubstituted alkyl group with the carbon number of C1-C6 and a substituted or unsubstituted aromatic group with the carbon number of C6-C12; x represents an O atom, an S atom, a sulfoxide group or a sulfone group.
Preferably, the electron donating group DD is selected from the group consisting of structures represented by the following general formula:
wherein R is4、R5、R6Each independently represents hydrogen, halogen, substituted or unsubstituted alkyl with carbon number of C1-C6, substituted or unsubstituted aryl with carbon number of C6-C12, or substituted or unsubstituted nitrogen-containing heteroaryl with carbon number of C6-12.
In the substituent, the halogen is fluorine atom, chlorine atom, bromine atom or iodine atom; the substituted or unsubstituted alkyl group is methyl, ethyl, propyl, butyl, pentyl, hexyl, trifluoromethyl, pentafluoroethyl; the substituted or unsubstituted aryl is phenyl, tolyl, ethylphenyl, propylphenyl, butylphenyl, pentylphenyl, hexylphenyl, fluorophenyl, fluoro-substituted tolyl, fluoro-substituted ethylphenyl, fluoro-substituted propylphenyl, fluoro-substituted butylphenyl, fluoro-substituted pentylphenyl, fluoro-substituted hexylphenyl, naphthyl, methylnaphthyl, ethylnaphthyl, trifluoromethylnaphthyl, fluoro-substituted naphthyl, biphenyl, methylbiphenyl, dimethylbiphenyl; the substituted or unsubstituted nitrogen-containing heteroaryl group is pyridyl, pyrazinyl, pyrimidinyl, pyridyl, triazinyl, fluoro-substituted pyridyl, fluoro-substituted pyrazinyl, fluoro-substituted pyrimidinyl, fluoro-substituted pyridyl, fluoro-substituted triazinyl, trifluoromethyl-substituted pyridyl, trifluoromethyl-substituted pyrazinyl, trifluoromethyl-substituted pyrimidinyl, trifluoromethyl-substituted pyridyl, trifluoromethyl-substituted triazinyl, benzopyridyl, benzopyrazinyl, benzopyrimidinyl, benzotriazinyl, methyl-substituted benzopyridyl, methyl-substituted benzopyrazinyl, methyl-substituted benzopyrimidinyl, methyl-substituted benzotriazinyl.
Preferably, the electron withdrawing group AA has a structure represented by the following general formula:
wherein, ring Z1Represents a substituted or unsubstituted hydrocarbon aromatic ringA hydrocarbon aromatic condensed ring, a five-membered nitrogen-containing heterocyclic ring, a six-membered nitrogen-containing heterocyclic ring, a benzo five-membered nitrogen-containing heterocyclic ring and a benzo six-membered nitrogen-containing heterocyclic ring; ring Z2、Z3Each independently represents an unsubstituted group, or a substituted or unsubstituted hydrocarbon aromatic ring, hydrocarbon aromatic condensed ring, five-membered nitrogen-containing heterocycle, six-membered nitrogen-containing heterocycle, benzo five-membered nitrogen-containing heterocycle and benzo six-membered nitrogen-containing heterocycle; ring Z1、Z2、Z3Connected by a single bond.
Preferably, said ring Z1、Z2、Z3Each independently represents a triazine ring, a pyrazine ring, a pyrimidine ring, a pyridine ring, a benzene ring, an alkyl-substituted triazine ring, an alkyl-substituted pyrazine ring, an alkyl-substituted pyrimidine ring, an alkyl-substituted pyridine ring, an alkyl-substituted benzene ring, a fluorine-substituted triazine ring, a fluorine-substituted pyrazine ring, a fluorine-substituted pyrimidine ring, a fluorine-substituted pyridine ring, a fluorine-substituted benzene ring, an indole ring, a quinoline ring, a pteridine ring, an acridine ring, an alkyl-substituted indole ring, an alkyl-substituted quinoline ring, an alkyl-substituted pteridine ring, an alkyl-substituted acridine ring, a fluorine-substituted indole ring, a fluorine-substituted quinoline ring, a fluorine-substituted pteridine ring, a fluorine-substituted acridine ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyrene ring, a perylene ring, a benzophenanthrene ring, an alkyl-substituted naphthalene ring, an alkyl-substituted anthracene ring, an alkyl-substituted phenanthrene ring, an alkyl-substituted pyrene ring, an alkyl-substituted perylene ring, an alkyl-substituted benzophenanthrene ring, A fluorine-substituted naphthalene ring, a fluorine-substituted anthracene ring, a fluorine-substituted phenanthrene ring, a fluorine-substituted pyrene ring, a fluorine-substituted perylene ring or a fluorine-substituted benzophenanthrene ring; wherein the alkyl group represents a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a fluoro-substituted methyl group, a fluoro-substituted ethyl group, a fluoro-substituted propyl group, a fluoro-substituted butyl group, a fluoro-substituted pentyl group or a fluoro-substituted hexyl group.
When the structure of the tris-s-triazine compound is selected from the general formula (I), the tris-s-triazine compound is preferably selected from the group consisting of the following structures:
when the structure of the tris-s-triazine compound is selected from the general formula (II), the tris-s-triazine compound is selected from the group consisting of the following structures:
the tris-s-triazine compound can adopt a general coupling synthesis method. The introduction of aromatic amine group can be described in New chemical journal (New j. chem.,2011,35, 953-. The method for introducing aromatic groups can be obtained by reacting organic boric acid and organic Grignard reagent by referring to the descriptions of domestic and foreign patents (WO2008117826, CN103435597A) and journal literature (chem. Mater.,2010,22,2403-2410, chem. Mater.,2013,25, 3758-3765).
The tris-s-triazine compound provided by the invention is described in detail below by combining a synthesis method and product performance.
Example 1
Synthesis of Compound I-1, Compound I-1 has the following structure:
adding 0.2mol of carbazole and 0.1mol of trichlorotriazine into 500mL of toluene, stirring at normal temperature for 24 hours, removing the solvent by suction filtration, adding the obtained precipitate into 500mL of toluene again, adding 0.15mol of diphenylamine, heating and refluxing for 2 hours, filtering to remove the solvent, and obtaining the solid, namely the target compound (I-1). Reaction yield 20%, MDLAI-TOF: 670. MDLAI-TOF is Matrix-assisted laser desorption Ionization Time of Flight Mass Spectrometry (Matrix-assisted laser desorption Ionization Time of Flight Mass Spectrometry, MALDI-TOF for short) and is used for detecting whether an experimental compound is the molecular weight of a target compound.
Example 2
Synthesis of Compound I-2, Compound I-2 has the following structure:
adding 0.2mol of carbazole and 0.1mol of trichlorotriazine into 500mL of toluene, stirring at normal temperature for 8 hours, then removing the solvent by suction filtration, adding the obtained precipitate into 500mL of toluene again, adding 0.2mol of dimethylaniline, heating and refluxing for 2 hours, filtering to remove the solvent, and obtaining the solid, namely the target compound (I-2). Reaction yield 29%, MDLAI-TOF: 698.
example 3
Synthesis of Compound I-3, Compound I-3 has the following structure:
adding 0.2mol of carbazole and 0.1mol of trichlorotriazine into 500mL of dimethylbenzene, stirring for 5 hours at normal temperature, removing the solvent by suction filtration, adding the obtained precipitate into new 500mL of dimethylbenzene again, adding 0.12mol of bis (4-trifluoromethyl) aniline, heating and refluxing for 2 hours, and filtering to remove the solvent to obtain a solid, namely the target compound (I-3). Reaction yield 31%, MDLAI-TOF: 806.
example 4
Synthesis of Compound I-4, Compound I-4 has the following structure:
adding 0.1mol of carbazole and 0.1mol of trichlorotriazine into 500mL of dimethylbenzene, stirring for 8 hours at normal temperature, removing the solvent by suction filtration, adding the obtained precipitate into new 500mL of dimethylbenzene again, adding 0.4mol of phenyl-2-naphthylamine, heating and refluxing for 2 hours, and filtering to remove the solvent to obtain a solid, namely the target compound (I-4). Reaction yield 21%, MDLAI-TOF: 772.
example 5
Synthesis of Compound I-5, Compound I-5 has the following structure:
adding 0.4mol of raw material aromatic amine (I-5a) and 0.1mol of trichloro-tris-s-triazine into 500mL of dimethylbenzene, stirring at normal temperature for 2 hours, heating and refluxing for 2 hours, filtering to remove the solvent, and obtaining a solid, namely the target compound (I-5). Reaction yield 30%, MDLAI-TOF: 1164.
example 6
Synthesis of Compound I-6, Compound I-6 has the following structure:
adding 0.2mol of carbazole and 0.1mol of trichlorotriazine into 500mL of toluene, stirring for 8 hours at normal temperature, removing the solvent by suction filtration, adding the obtained precipitate into 500mL of toluene again, adding 200mL of ethanol, 300mL of 2mol/L sodium carbonate solution, 0.1mmol of tetrakis (triphenylphosphine) palladium, 0.15mol of 2-naphthalene boric acid, and reacting for 18 hours at 100 ℃ under the protection of nitrogen. Cooling, extracting with ethyl acetate, removing solvent by rotary evaporation, and separating with chromatographic column to obtain target compound (I-6). Reaction yield 11%, MDLAI-TOF: 629.
example 7
Synthesis of Compound I-7, Compound I-7 has the following structure:
adding 0.2mol of carbazole and 0.1mol of trichlorotriazine into 500mL of toluene, stirring at normal temperature for 6 hours, removing the solvent by suction filtration, adding the obtained precipitate into 500mL of toluene again, adding 200mL of ethanol, 300mL of 2mol/L sodium carbonate solution, 0.1mmol of tetrakis (triphenylphosphine) palladium, 0.15mol of 2, 6-bis (trifluoromethyl) pyridine-4-boric acid, and reacting at 100 ℃ for 36 hours under the protection of nitrogen. Cooling, extracting with ethyl acetate, removing solvent by rotary evaporation, and separating with chromatographic column to obtain target compound (I-7). Reaction yield 14%, MDLAI-TOF: 716.
example 8
Synthesis of Compound I-8, Compound I-8 has the following structure:
adding 0.2mol of carbazole and 0.1mol of trichlorotriazine into 500mL of toluene, stirring at normal temperature for 6 hours, removing the solvent by suction filtration, adding the obtained precipitate into 500mL of toluene again, adding 200mL of ethanol, 300mL of 2mol/L sodium carbonate solution, 0.1mmol of tetrakis (triphenylphosphine) palladium, 0.15mol of 4- (2-pyridyl) -phenylboronic acid, and reacting at 100 ℃ for 24 hours under the condition of nitrogen protection. Cooling, extracting with ethyl acetate, removing solvent by rotary evaporation, and separating with chromatographic column to obtain target compound (I-8). Reaction yield 19%, MDLAI-TOF: 656.
example 9
Synthesis of Compound I-9, Compound I-9 has the following structure:
adding 0.1mol of raw material aromatic amine (I-9a) and 0.1mol of trichloro-tris-s-triazine into 500mL of toluene, stirring for 6 hours at normal temperature, removing the solvent by suction filtration, adding the obtained precipitate into 500mL of new toluene again, adding 200mL of ethanol, 300mL of 2mol/L sodium carbonate solution, 0.2mmol of tetrakis (triphenylphosphine) palladium, 0.4mol of phenylboronic acid and reacting for 12 hours at 110 ℃ under the protection of nitrogen. Cooling, extracting with ethyl acetate, removing solvent by rotary evaporation, and separating with chromatographic column to obtain target compound (I-9). Reaction yield 26%, MDLAI-TOF: 655.
example 10
Synthesis of Compound I-10, Compound I-10 has the following structure:
adding 0.1mol of biphenylamine and 0.1mol of trichlorotriazine into 500mL of toluene, stirring for 6 hours at normal temperature, removing the solvent by suction filtration, adding the obtained precipitate into 500mL of new toluene again, adding 200mL of ethanol, 300mL of 2mol/L sodium carbonate solution, 0.2mmol of tetrakis (triphenylphosphine) palladium, 0.4mol of phenylboronic acid, and reacting for 12 hours at 110 ℃ under the protection of nitrogen. Cooling, extracting with ethyl acetate, removing solvent by rotary evaporation, and separating with chromatographic column to obtain target compound (I-10). Reaction yield 28%, MDLAI-TOF: 644.
example 11
Synthesis of Compound I-11, Compound I-11 has the following structure:
adding 0.2mol of diphenylamine and 0.1mol of trichlorotriazine into 500mL of toluene, stirring at normal temperature for 6 hours, removing the solvent by suction filtration, adding the obtained precipitate into 500mL of toluene again, adding 200mL of ethanol, 300mL of 2mol/L sodium carbonate solution, 0.2mmol of tetrakis (triphenylphosphine) palladium, 0.3mol of trifluoromethylphenylboronic acid and reacting at 110 ℃ for 12 hours under the protection of nitrogen. Cooling, extracting with ethyl acetate, removing solvent by rotary evaporation, and separating with chromatographic column to obtain target compound (I-11). Reaction yield 33%, MDLAI-TOF: 651.
example 12
Synthesizing a compound II-1, wherein the structure of the compound II-1 is as follows:
adding 0.2mol of 4- (9-carbazolyl) -phenylboronic acid and 0.1mol of trichloro-tris-sym-triazine into a mixed solvent of 400mL of toluene, 180mL of ethanol and 180mL of 2mol/L sodium carbonate solution, adding 0.1mmol of catalyst tetrakis (triphenylphosphine) palladium, stirring and refluxing at 115 ℃ for 48 hours under the protection of nitrogen, cooling, extracting with ethyl acetate, removing the solvent by rotary evaporation, and separating by a chromatographic column to obtain an intermediate. And adding the intermediate and 0.1mol of 1-naphthalene boric acid into a mixed solvent of 400mL of toluene, 180mL of ethanol and 180mL of 2mol/L sodium carbonate solution, adding 0.1mmol of catalyst tetrakis (triphenylphosphine) palladium, stirring and refluxing at 115 ℃ for 48 hours under the protection of nitrogen, cooling, extracting with ethyl acetate, removing the solvent by rotary evaporation, and separating by a chromatographic column to obtain the target compound (II-1). Reaction yield 17%, MDLAI-TOF: 781.
example 12
And (3) synthesizing a compound II-2, wherein the compound II-2 has the following structure:
adding 0.2mol of 4- (9-carbazolyl) -phenylboronic acid and 0.1mol of trichloro-tris-sym-triazine into a mixed solvent of 400mL of toluene, 180mL of ethanol and 180mL of 2mol/L sodium carbonate solution, adding 0.1mmol of catalyst tetrakis (triphenylphosphine) palladium, stirring and refluxing at 115 ℃ for 48 hours under the protection of nitrogen, cooling, extracting with ethyl acetate, removing the solvent by rotary evaporation, and separating by a chromatographic column to obtain an intermediate. And (2) putting the intermediate and 0.1mol of 9-phenylcarbazole-3-boric acid into a mixed solvent of 400mL of toluene, 180mL of ethanol and 180mL of 2mol/L sodium carbonate solution, adding 0.1mmol of catalyst tetrakis (triphenylphosphine) palladium, stirring and refluxing for 48 hours at 115 ℃ under the protection of nitrogen, cooling, extracting with ethyl acetate, removing the solvent by rotary evaporation, and separating by a chromatographic column to obtain the target compound (II-2). Reaction yield 14%, MDLAI-TOF: 896.
based on the tris-s-triazine compound, the present invention provides a light-emitting device using the tris-s-triazine compound.
Fig. 1 is a schematic structural diagram of a light emitting device according to the present invention. The light-emitting device 100 includes an anode 11, a hole transport layer 12, a light-emitting layer 13, an electron transport layer 14, and a cathode 15, which are sequentially deposited. Wherein the hole transport layer 12, the light emitting layer 13 and the electron transport layer 14 are all organic layers, and the anode 11 is electrically connected with the cathode 15.
The light-emitting layer 13 may only be the tris-s-triazine compound provided by the present invention, so that the light-emitting device 100 is an undoped device. The light-emitting layer 13 may also comprise other materials, making the light-emitting device 100 a doped device. When a doped device is used, the proportion of the tris-s-triazine compound provided by the present invention in the light-emitting layer 13 is not limited. Generally, when the tris-s-triazine compound provided by the invention accounts for the main proportion, the tris-s-triazine compound is used as a main material; when the tris-s-triazine compound provided by the invention accounts for a minor proportion, the tris-s-triazine compound is used as a guest doping material. The host material is required to be able to transfer energy to the guest dopant material. When a doped device is used, the doping ratio is not limited, and generally ranges from 1 to 45%, preferably from 2 to 20%, and more preferably from 3 to 10%.
The hole transport layer 12 may be a tris-s-triazine compound provided by the present invention, or may be a hole transport layer selected from other aromatic amine-based organic compounds as long as the introduced holes can be transferred to the light-emitting layer 13. The hole transport layer 12 may be one layer or may be a plurality of layers.
The electron transport layer 14 may be the tris-s-triazine compound provided by the present invention, or may be another compound selected as the electron transport layer, and there is no specific requirement on the compound structure of the electron transport layer as long as the introduced electrons can be transferred to the light emitting layer. As the compound structure of the electron transport layer 14, a nitrogen-containing heterocyclic compound, a spiro aromatic compound composed of a hydrocarbon element, or a metal complex may be selected. The electron transport layer 14 may be one layer or may be a plurality of layers.
In order to schematically prove the excellent characteristics of the tris-s-triazine compound provided by the invention as a light-emitting device material, the light-emitting device is designed according to the following structure: anode/hole transport layer/host material: the tris-s-triazine compound/electron transport layer/cathode provided by the invention is taken as a guest material.
The manufacturing process of the light emitting device 100 is as follows:
ultrasonically treating a glass plate coated with an Indium Tin Oxide (ITO) transparent conductive layer in a commercial cleaning agent, washing with deionized water, ultrasonically treating the glass plate in an acetone-ethanol mixed solvent, baking in a clean environment to completely remove moisture, exposing the glass plate for 20 minutes by using an ultraviolet light cleaning agent, placing the cleaned glass substrate in a vacuum chamber, and vacuumizing to 1 × 10-3～10-5Pa, evaporating a layer of 4, 4' -cyclohexyl-bis [ N, N-bis (4-methylphenyl) aniline](TAPC) as a hole transport layer, with an evaporation rate of 0.1-0.2nm/s and an evaporation thickness of 10-100 nm; continuously evaporating a luminescent layer containing the tris-s-triazine compound and 4, 4' -bis (9-Carbazole) Biphenyl (CBP), wherein the doping concentration is 1-20 wt%, the evaporation rate is 0.1-0.2nm/s, and the thickness is 10-50 nm; continuously evaporating a layer of bis (2-methyl-8-hydroxyquinoline-N1, O8) - (1,1' -biphenyl-4-hydroxy) aluminum (BALq), wherein the evaporation rate is 0.1-0.2nm/s, and the thickness is 10-50 nm; and continuously evaporating a layer of magnesium-silver electrode, wherein the evaporation rate is 1-2nm/s, and the thickness is 20-200 nm.
The structure of the light emitting device 100 formed by the above-described manufacturing process is: ITO/TAPC/CBP tris-s-triazine compounds of the invention/BALq/Mg Ag.
The functional material and the main material used by the invention have the following structures:
to further illustrate the excellent characteristics of the tris-s-triazine compounds provided by the present invention in light emitting devices, the light emitting devices 100 of examples 1-12 were fabricated by using the tris-s-triazine compounds of different structures in combination with the above fabrication process, respectively, and the structures of the light emitting devices 100 were ITO/TAPC/CBP: tris-s-triazine compounds of the present invention/BAlq/Mg: Ag. Meanwhile, the light emitting devices of comparative examples 1 and 2 were prepared using the tris-s-triazine compound (a) in the background art, and the light emitting devices of the present invention were compared with those of the comparative examples in terms of performance.
The light-emitting device structures of examples 1 to 6 had TAPC of 90nm, a light-emitting layer of 40nm, BAlq of 30nm, and a Mg: Ag electrode of 100 nm. The test results were as follows:
according to the data result analysis, the luminescent device adopting the tris-s-triazine compound not only maintains ultrahigh external quantum efficiency, but also has long service life. Where device lifetime is the lifetime of 80% decay to initial brightness under packaging conditions.
Compared with the related art, the tris-s-triazine compound provided by the invention has the beneficial effects that:
firstly, the tris-s-triazine compound maintains a D-pi-A structure and maintains the performance of TADF; the substituent group contains an aromatic or heteroaromatic structure, so that the glass transition temperature is high, and the heat resistance is good; the substituent groups are different, the molecules have asymmetric structures, the crystallization is not easy, and the film forming property is good.
Secondly, when the tris-s-triazine compound is applied to a light-emitting device, the maximum external quantum efficiency exceeds the theoretical external quantum efficiency of a fluorescent material, and the tris-s-triazine compound provided by the invention is considered to have the performance of a TADF material.
While the foregoing is directed to embodiments of the present invention, it will be understood by those skilled in the art that various changes may be made without departing from the spirit and scope of the invention.

Claims (9)

1. A tris-s-triazine compound of the general formula:
wherein,
DA1、DA2each independently represents an electron donating group DD having a carbon number of C12-C60 or an electron withdrawing group AA having a carbon number of C12-C60;
electron donating group DD represents an organic group having at least one nitrogen atom that is sp3 hybridized;
the electron-withdrawing group AA represents an organic group having at least one nitrogen atom hybridized with sp2, or an aromatic group composed of substituted or unsubstituted hydrocarbon elements;
in the general formula (II), ring Y1、Y2、Y3Each independently represents a substituted or unsubstituted triazine ring, pyrazine ring, pyrimidine ring, pyridine ring or benzene ring.
2. Tris-triazine compound according to claim 1, wherein the electron donating group DD is selected from the group consisting of structures represented by the following general formulae:
wherein R is1、R2、R3Each independently represents hydrogen, halogen, substituted or unsubstituted alkyl with carbon number of C1-C6, substituted or unsubstituted aryl with carbon number of C6-C12, or substituted or unsubstituted nitrogen-containing heteroaryl with carbon number of C6-C12; r11、R12Are connected by covalent bonds and respectively and independently represent a substituted or unsubstituted alkyl group with the carbon number of C1-C6 and a substituted or unsubstituted aromatic group with the carbon number of C6-C12; x represents an O atom, an S atom, a sulfoxide group or a sulfone group.
3. Tris-triazine compound according to claim 1, wherein the electron donating group DD is selected from the group consisting of structures represented by the following general formulae:
wherein R is4、R5、R6Each independently represents hydrogen, halogen, substituted or unsubstituted alkyl with carbon number of C1-C6, substituted or unsubstituted aryl with carbon number of C6-C12, or substituted or unsubstituted nitrogen-containing heteroaryl with carbon number of C6-12.
4. Tris-s-triazine compound according to claim 2 or 3, wherein the halogen is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom; the substituted or unsubstituted alkyl group is methyl, ethyl, propyl, butyl, pentyl, hexyl, trifluoromethyl, pentafluoroethyl; the substituted or unsubstituted aryl is phenyl, tolyl, ethylphenyl, propylphenyl, butylphenyl, pentylphenyl, hexylphenyl, fluorophenyl, fluoro-substituted tolyl, fluoro-substituted ethylphenyl, fluoro-substituted propylphenyl, fluoro-substituted butylphenyl, fluoro-substituted pentylphenyl, fluoro-substituted hexylphenyl, naphthyl, methylnaphthyl, ethylnaphthyl, trifluoromethylnaphthyl, fluoro-substituted naphthyl, biphenyl, methylbiphenyl, dimethylbiphenyl; the substituted or unsubstituted nitrogen-containing heteroaryl group is pyridyl, pyrazinyl, pyrimidinyl, pyridyl, triazinyl, fluoro-substituted pyridyl, fluoro-substituted pyrazinyl, fluoro-substituted pyrimidinyl, fluoro-substituted pyridyl, fluoro-substituted triazinyl, trifluoromethyl-substituted pyridyl, trifluoromethyl-substituted pyrazinyl, trifluoromethyl-substituted pyrimidinyl, trifluoromethyl-substituted pyridyl, trifluoromethyl-substituted triazinyl, benzopyridyl, benzopyrazinyl, benzopyrimidinyl, benzotriazinyl, methyl-substituted benzopyridyl, methyl-substituted benzopyrazinyl, methyl-substituted benzopyrimidinyl, methyl-substituted benzotriazinyl.
5. Tris-s-triazine compound of claim 1, wherein the electron withdrawing group AA has a structure represented by the following general formula:
wherein, ring Z1Represents a substituted or unsubstituted hydrocarbon aromatic ring, a hydrocarbon aromatic condensed ring, a five-membered nitrogen-containing heterocyclic ring, a six-membered nitrogen-containing heterocyclic ring, a benzo five-membered nitrogen-containing heterocyclic ring, a benzo six-membered nitrogen-containing heterocyclic ring; ring Z2、Z3Each independently represents an unsubstituted group, or a substituted or unsubstituted hydrocarbon aromatic ring, hydrocarbon aromatic condensed ring, five-membered nitrogen-containing heterocycle, six-membered nitrogen-containing heterocycle, benzo five-membered nitrogen-containing heterocycle and benzo six-membered nitrogen-containing heterocycle; ring Z1、Z2、Z3Connected by a single bond.
6. Tri-s-triazine compound according to claim 5, wherein the ring Z is1、Z2、Z3Each independently represents a triazine ring, a pyrazine ring, a pyrimidine ring, a pyridine ring, a benzene ring, an alkyl-substituted triazine ring, an alkyl-substituted pyrazine ring, an alkyl-substituted pyrimidine ring, an alkyl-substituted pyridine ring, an alkyl-substituted benzene ring, a fluorine-substituted triazine ring, a fluorine-substituted pyrazine ring, a fluorine-substituted pyrimidine ring, a fluorine-substituted pyridine ring, a fluorine-substituted benzene ring, an indole ring, a quinoline ring, a pteridine ring, an acridine ring, an alkyl-substituted indole ring, an alkyl-substituted quinoline ring, an alkyl-substituted pteridine ring, an alkyl-substituted acridine ring, a fluorine-substituted indole ring, a fluorine-substituted quinoline ring, a fluorine-substituted pteridine ring, a fluorine-substituted acridine ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyrene ring, a perylene ring, a benzophenanthrene ring, an alkyl-substituted naphthalene ring, an alkyl-substituted anthracene ring, an alkyl-substituted phenanthrene ring, an alkyl-substituted pyrene ring, an alkyl-substituted perylene ring, an alkyl-substituted benzophenanthrene ring, A fluorine-substituted naphthalene ring, a fluorine-substituted anthracene ring, a fluorine-substituted phenanthrene ring, a fluorine-substituted pyrene ring, a fluorine-substituted perylene ring or a fluorine-substituted benzophenanthrene ring; wherein the alkyl group represents a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a fluoro-substituted methyl group, a fluoro-substituted ethyl group, a fluoro-substituted propyl group, a fluoro-substituted butyl group, a fluoro-substituted pentyl group or a fluoro-substituted hexyl group.
7. Tris-s-triazine compound according to claim 1, selected from the group consisting of the following structures:
8. tris-s-triazine compound according to claim 1, selected from the group consisting of the following structures:
9. a light-emitting device comprising an anode, a cathode, and a plurality of organic layers provided between the anode and the cathode, wherein at least one of the plurality of organic layers contains the tris-s-triazine compound according to any one of claims 1 to 8.
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CN110591697A (en) * 2019-09-02 2019-12-20 武汉华星光电半导体显示技术有限公司 Thermal activation delayed fluorescent material, preparation method thereof and electroluminescent device
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