CN110078727B - Organic electroluminescent compound, preparation method thereof and organic electroluminescent device - Google Patents

Organic electroluminescent compound, preparation method thereof and organic electroluminescent device Download PDF

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CN110078727B
CN110078727B CN201910450883.9A CN201910450883A CN110078727B CN 110078727 B CN110078727 B CN 110078727B CN 201910450883 A CN201910450883 A CN 201910450883A CN 110078727 B CN110078727 B CN 110078727B
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CN110078727A (en
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马晓宇
王进政
汪康
孙毅
毕岩
赵贺
孙峰
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

The invention relates to an organic electroluminescent compound, a preparation method thereof and an organic electroluminescent device, wherein the structural formula of the organic electroluminescent compound is shown as chemical formula 1:

Description

Organic electroluminescent compound, preparation method thereof and organic electroluminescent device
Technical Field
The invention relates to the technical field of luminescent materials, in particular to an organic electroluminescent compound, a preparation method thereof and an organic electroluminescent device.
Background
The organic EL element is a self-luminous element utilizing the following principle: by applying an electric field, the fluorescent substance emits light by the recombination energy of holes injected from the anode and electrons injected from the cathode. It has a structure of an anode, a cathode and an organic layer interposed therebetween. In order to improve the efficiency and stability of the organic EL device, the organic layer needs to have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. Wherein the hole transport layer can change hole transport efficiency, light emitting efficiency, lifetime, etc. of holes to the light emitting layer.
Examples of conventional triarylamine compounds used as a material having a hole transporting property in an OLED include 4,4',4 ″ -tris- (3-methylphenyl-phenylamino) -triphenylamine (MTDATA), 4' -bis [ N- (1-naphthyl) -N-phenylamino ] biphenyl (NPB), N '-diphenyl-N, N' -bis (3-methylphenyl) - (1,1 '-biphenyl) -4, 4' -diamine (TPD), and the like. However, although the use of the above materials can improve the performance of the organic EL device, the organic EL device using these materials still has problems in terms of starting voltage, luminous efficiency, service life, and the like.
Disclosure of Invention
The present invention is directed to solving the technical problems of the prior art and provides an organic electroluminescent compound having a novel structure with excellent current efficiency and long lifetime, a method for preparing the same, and an organic electroluminescent device.
In order to solve the technical problems, the technical scheme of the invention is as follows:
the invention provides an organic electroluminescent compound, the structural formula of which is shown in chemical formula 1:
Figure BDA0002075109950000021
wherein:
Ar1and Ar2Each independently represents a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted 3-to 30-membered heteroaryl group; or are linked to an adjacent substituent(s) to form a mono-or polycyclic, in particular C3-C30, aliphatic or aromatic ring whose carbon atom(s) may be replaced by at least one heteroatom selected from nitrogen, oxygen and sulfur;
R0represents 4 hydrogen atoms on the benzene ring, any one or more of which are R0May be replaced by deuterium; t is 4;
R1and R2Each independently represents hydrogen, deuterium, halogen, cyano, carboxyl, nitroA hydroxyl, a substituted or unsubstituted C1-C30 alkyl, a substituted or unsubstituted C2-C30 alkenyl, a substituted or unsubstituted C2-C30 alkynyl, a substituted or unsubstituted C1-C30 alkoxy, a substituted or unsubstituted C3-C30 cycloalkyl, a substituted or unsubstituted C3-C30 cycloalkenyl, a substituted or unsubstituted 3-to 7-membered heterocycloalkyl, a substituted or unsubstituted C6-C30 aryl, or a substituted or unsubstituted 3-to 30-membered heteroaryl; or are linked to an adjacent substituent(s) to form a substituted or unsubstituted, mono-or polycyclic, specifically C3-C30, aliphatic or aromatic ring, the carbon atom(s) of which may be replaced with at least one heteroatom selected from nitrogen, oxygen and sulfur;
R3and R4Each independently represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted 3-to 7-membered heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted 3-to 30-membered heteroaryl;
x is-O-, -S-, -C (R)5)(R6)-、-N(R7) -or-Si (R)8)(R9)-；
Y is- [ C (R)10)c(R11)d]m-；
R5To R11Each independently represents a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 cycloalkenyl group, a substituted or unsubstituted 3-to 7-membered heterocycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted 3-to 30-membered heteroaryl group; or are linked to adjacent substituents to form a substituted or unsubstituted, mono-or polycyclic, in particular C3-C30, aliphatic or aromatic ring, whose carbon atoms may beReplacement by at least one heteroatom selected from nitrogen, oxygen and sulfur;
ring G represents substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted 3-to 7-membered heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted 3-to 30-membered heteroaryl;
a. b, c and d each independently represent an integer of 0 to 2, and m and n each independently represent 0 or 1.
In the above technical scheme, when n is 0, R1The ring G, which is linked to the ring G already shown in the formula, forms a substituted or unsubstituted polycyclic, in particular C3-C30, aliphatic or aromatic ring, the carbon atoms of which may be replaced by one or more of nitrogen, oxygen, sulfur and silicon heteroatoms.
In the above technical solutions, R is preferable3And R4Each independently represents methyl, hexyl, isopropyl, tert-butyl, a benzene ring, a naphthalene ring or pyridine.
In the above-mentioned technical solution,
Figure BDA0002075109950000031
and Ar1And Ar2May preferably be selected from any one of the following structures:
Figure BDA0002075109950000041
wherein R is hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, amino, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted 3-to 7-membered heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted 3-to 30-membered heteroaryl; or are linked to an adjacent substituent(s) to form a substituted or unsubstituted, mono-or polycyclic, specifically C3-C30, aliphatic or aromatic ring, the carbon atom(s) of which may be replaced with at least one heteroatom selected from nitrogen, oxygen and sulfur; and said-R represents at any position of the ring in which it is located; wherein ". mark" is a connecting position and indicates any position of the ring in which the connecting position is located.
The alkyl is straight-chain alkyl, branched-chain alkyl, cycloalkyl, straight-chain alkyl substituted by at least 1 substituent, branched-chain alkyl substituted by at least 1 substituent or cycloalkyl substituted by at least 1 substituent; wherein, the substituent is one or more of halogen, cyano, hydroxyl and sulfydryl.
The aryl group in the present invention is preferably an unsubstituted aryl group or an aryl group substituted with at least 1 substituent; wherein the substituents are independently selected from halogen, amino, cyano, nitro, hydroxy or mercapto.
The heteroaryl group of the present invention is preferably an unsubstituted heteroaryl group or a heteroaryl group substituted with at least 1 substituent; wherein the heteroatom in the heteroaryl group is nitrogen, sulfur or oxygen; the substituents are independently selected from halogen, amino, cyano, nitro, hydroxy or mercapto.
In the above technical solution, it is most preferable that the organic electroluminescent compound is any one of the following structures:
Figure BDA0002075109950000051
Figure BDA0002075109950000061
Figure BDA0002075109950000071
Figure BDA0002075109950000081
Figure BDA0002075109950000091
the organic electroluminescent compounds according to the invention can be prepared by synthetic methods known to the person skilled in the art. Preferably, it can be prepared according to the following reaction scheme. The preparation method of the organic electroluminescent compound comprises the following steps:
step 1: reacting compound 1 with compound 2 to prepare compound 3;
step 2: reacting compound 3 with compound 4 to prepare compound 5;
and step 3: reacting compound 5 with compound 6 to produce compound 7;
and 4, step 4: dissolving the compound 7 in tetrahydrofuran, diluting sodium hypochlorite and sulfamic acid with water, adding the diluted sodium hypochlorite and sulfamic acid into a reactant, and heating and stirring the reactant to react to obtain a compound 8;
and 5: placing the compound 8 in tetrahydrofuran, stirring, adding polyphosphoric acid, heating, stirring and reacting to obtain a compound 9;
step 6: reacting compound 10 with compound 9 to produce compound 11;
and 7: reacting the compound 11 with the compound 12 to prepare a compound shown in a chemical formula 1;
the synthetic route is as follows:
Figure BDA0002075109950000101
wherein R1～R4、Ar1、Ar2X, Y, ring G, and a, b, n and t are as defined above in formula 1, and Z represents halogen.
In the above technical solution, it is preferable that the method for manufacturing an organic electroluminescent compound according to the present invention comprises the steps of:
step 1: preparation of Compound 3
Placing the compound 1 and sodium tert-butoxide in toluene, adding the compound 2, a palladium acetate catalyst and BINAP under the protection of nitrogen, heating to 90 ℃ for reaction for 8 hours, after the reaction is finished, adding water for washing, extracting with ethyl acetate, drying an organic phase, and separating and purifying by a silica gel chromatographic column to obtain a compound 3;
step 2: preparation of Compound 5
Adding the compound 3 and the compound 4 into a mixed solvent of toluene and ethanol, then adding p-toluenesulfonic acid, carrying out reflux reaction for 12 hours, after the reaction is finished, adding water for washing, carrying out DCM extraction, drying an organic phase, and carrying out separation and purification by using a silica gel chromatographic column to obtain a compound 5;
and step 3: preparation of Compound 7
Putting the compound 5 and the compound 6 into DMF, adding anhydrous potassium carbonate, heating and stirring, adding copper oxide at 50 ℃, and heating to reflux reaction for 24 hours; after the reaction is finished, cooling to room temperature, filtering to remove redundant inorganic salt, adding a hydrochloric acid aqueous solution, heating to 60 ℃, stirring for reaction for 4 hours, cooling to room temperature, adding water for washing, extracting with ethyl acetate, drying an organic phase, and separating and purifying by using a silica gel chromatographic column to obtain a compound 7;
and 4, step 4: preparation of Compound 8
Dissolving the compound 7 in tetrahydrofuran, diluting sodium hypochlorite and sulfamic acid with water, adding the diluted sodium hypochlorite and sulfamic acid into a reactant, and heating and stirring for 4 hours; after the reaction is finished, cooling the temperature to normal temperature, and extracting with water and ethyl acetate to separate an organic layer; treating the organic layer with anhydrous magnesium sulfate, filtering, and concentrating under reduced pressure; recrystallizing the solid with ethyl acetate and petroleum ether to obtain a compound 8;
and 5: preparation of Compound 9
Placing the compound 8 in tetrahydrofuran, stirring, adding polyphosphoric acid, heating to 60 ℃, stirring for reacting for 12 hours, cooling to room temperature, washing with water, extracting with DCM, drying and concentrating an organic phase, and recrystallizing 1, 4-dioxane to obtain a compound 9;
step 6: preparation of Compound 11
Putting the compound 10 in tetrahydrofuran, cooling to-78 ℃, dropwise adding n-butyllithium, heating to room temperature for continuous reaction for 2 hours, cooling to-78 ℃ again, dropwise adding a tetrahydrofuran solution of the compound 9, then gradually heating to room temperature, and reacting for 16 hours; after the reaction is finished, quenching with dilute hydrochloric acid, extracting with ethyl acetate, drying an organic phase, and separating and purifying by using a silica gel chromatographic column to obtain a compound 11;
and 7: preparation of Compound represented by chemical formula 1
And (3) putting the compound 11 and the compound 12 in tetrahydrofuran, adding methanesulfonic acid and polyphosphoric acid, reacting at normal temperature for 10 hours, after the reaction is finished, adding water for washing, extracting with ethyl acetate, drying an organic phase, and recrystallizing with toluene to obtain the compound shown in the chemical formula 1.
The invention also provides an organic electroluminescent device containing the organic electroluminescent compound.
The above-mentioned device may contain the organic electroluminescent compound of the present invention alone, or may further include conventional materials generally used for organic electroluminescent materials.
The organic electroluminescent device comprises a first electrode, a second electrode, and at least one organic layer between the first and second electrodes; the organic layer may include at least one organic electroluminescent compound of chemical formula 1.
One of the first and second electrodes is an anode and the other is a cathode. The organic layer includes a light emitting layer, and further includes at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.
The organic electroluminescent compound according to the present invention may be contained in at least one of the light-emitting layer and the hole transport layer.
The invention has the beneficial effects that:
the present invention provides a hole transport material for use in an organic EL device that can solve the conventional technical problems. Although the conventional hole transport material has a hole transport ability and a low driving voltage, the ideal hole transport material requires a higher hole transport ability, a long life, and a high light emitting efficiency with the continuous improvement of the requirements for the comprehensive properties of the material. Therefore, the present invention proposes a solution to introduce a novel pyrroloacridine derivative in order to solve the problems of the conventional hole transport materials and to obtain a desired material. By introducing arylamine and novel pyrroloacridine derivatives, a high-quality organic electroluminescent material with excellent hole transport capability, high efficiency and long service life is obtained.
Compared with an organic electroluminescent device prepared by taking NPB as a hole transport layer, the organic electroluminescent device prepared by taking the organic electroluminescent compound provided by the invention as the hole transport layer has lower starting voltage, and the luminous efficiency and the service life are obviously improved.
The preparation method of the organic electroluminescent compound provided by the invention is simple and feasible, has high yield and is suitable for large-scale production.
Detailed Description
Synthesis example 1: preparation of intermediates 1 to 3
Figure BDA0002075109950000131
Benzophenone hydrazone (19.6g 100mmol), sodium tert-butoxide (19.2g 200mmol) are placed in dry toluene (500mL) and are added with bromobenzene (15.6g 100mmol), palladium acetate catalyst (1.1g 5mmol) and BINAP (6.23g 10mmol) under the protection of nitrogen, the temperature is raised to 90 ℃ for reaction for 8 hours, after the reaction is finished, water washing and ethyl acetate extraction are added, the organic phase is dried, and silica gel chromatographic column separation and purification are carried out to obtain intermediates 1-3(21.23g, 78%), MW: 272.23.
synthesis example 2: preparation of intermediates 1 to 5
Figure BDA0002075109950000132
Intermediate 1-3(20g 73.47mmol) and diphenylethanone (14.40g 73.47mmol) were added to a mixed solvent of toluene and ethanol (500mL Vtoluene: VEtOH ═ 4:1), followed by p-toluenesulfonic acid (63.25g 367.35mmol), refluxed for 12h, and after the reaction was completed, water was added for washing, DCM was added for extraction, the organic phase was dried, and silica gel column chromatography was used for purification to give intermediate 1-5(16.8g, 85%) MW: 269.12.
Synthetic example 3: preparation of intermediates 1 to 7
Figure BDA0002075109950000141
Intermediate 1-5(16.0g 59.45mmol) and o-bromobenzeneboronic acid (12.54g 62.43mmol) were placed in dry DMF (300mL), anhydrous potassium carbonate (24.69g 178.62mmol) was added, stirring was gradually increased in temperature, copper oxide (0.24g 3mmol) was added at 50 deg.C, and the reaction was heated to reflux for 24 h. After the reaction is finished, cooling to room temperature, filtering to remove excessive inorganic salt, adding 2M hydrochloric acid aqueous solution (360mL), heating to 60 ℃, stirring for reaction for 4 hours, cooling to room temperature, washing with water, extracting with ethyl acetate, drying an organic phase, and separating and purifying by a silica gel chromatography column to obtain an intermediate 1-7(17.75g, 80%) with MW: 373.64.
Synthetic example 4: preparation of intermediates 1 to 8
Figure BDA0002075109950000142
After dissolving intermediates 1 to 7(17.5g 46.84mmol) in 300mL of tetrahydrofuran, sodium hypochlorite (3.84g 51.52mmol) and sulfamic acid (6.82g 70.26mmol) were diluted with water (50 mL each) and added, followed by stirring with heating for 4 hours. After completion of the reaction, the temperature was lowered to room temperature, and the organic layer was separated by extraction with water and ethyl acetate. The organic layer was treated with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The solid was recrystallized from ethyl acetate and petroleum ether to give intermediates 1-8(16.77g, 92%) MW: 389.44.
Synthesis example 5: preparation of intermediates 1 to 9
Figure BDA0002075109950000151
Intermediate 1-8(16.5g 42.37mmol) was stirred in dry tetrahydrofuran (300mL), polyphosphoric acid (28.64g 84.74mmol) was added, heated to 60 deg.C, stirred for 12h, cooled to room temperature, washed with water, extracted with DCM, the organic phase was dried, concentrated, and recrystallized from 1, 4-dioxane to give intermediate 1-9(14.15g, 90%). MW: 337.90.
Synthetic example 6: preparation of intermediates 1 to 11
Figure BDA0002075109950000152
Bromobenzene (7.15g 45.57mmol) is placed in dry tetrahydrofuran (300mL), the temperature is reduced to-78 ℃, n-butyllithium (18.23mL 45.57mmol) is added dropwise, the temperature is slowly increased to room temperature, the reaction is continued for 2h, the temperature is reduced to-78 ℃ again, the tetrahydrofuran solution of intermediate 1-9(14.0g 41.43mmol) is added dropwise, and then the reaction is carried out for 16h after the temperature is gradually increased to room temperature. After the reaction, 1M diluted hydrochloric acid was quenched, extracted with ethyl acetate, the organic phase was dried, and separated and purified by silica gel column chromatography to obtain intermediate 1-11(13.96g, 75%) with MW: 499.32.
Synthetic example 7: preparation of Compound 1
Figure BDA0002075109950000161
Intermediate 1-11(13.5g, 27.0mmol) and triphenylamine (7.29g, 29.7mmol) were placed in tetrahydrofuran (300mL), methanesulfonic acid (5.18g, 54.0mmol) and polyphosphoric acid (18.25g, 54mmol) were added, reaction was carried out at room temperature for 10h, after completion of the reaction, water washing was added, extraction was carried out with ethyl acetate, the organic phase was dried, and recrystallization from toluene gave compound 1(16.43g, 90%) MW: 676.15.
Synthesis example 8: preparation of Compound 11
Figure BDA0002075109950000162
Compound 11(20.63g, 88%) was synthesized using intermediates 11-12 in the same manner as in example 7,
MW:868.11。
synthetic example 9: preparation of Compound 13
Figure BDA0002075109950000163
Compound 13(20.7g, 91%) MW 842.33 was synthesized according to the procedure for example 7, using intermediates 13-12.
Synthetic example 10: preparation of Compound 21
Figure BDA0002075109950000171
Compound 21(20.75g, 87%) MW 883.43 was synthesized according to the procedure for example 7, using intermediates 21-12.
Synthetic example 11: preparation of intermediates 28-11
Figure BDA0002075109950000172
Using intermediate 28-10, intermediate 28-11(16.75g, 77%) MW:525.13 was synthesized according to the procedure for example 6.
Synthesis example 12 preparation of Compound 28
Figure BDA0002075109950000173
Compound 28(26.54g, 92%) MW:904.63 was synthesized according to the procedure for example 7 using intermediates 28-11 and 28-12.
Synthesis example 13 preparation of intermediates 49-5
Figure BDA0002075109950000181
Intermediate 49-5(7.57g, 88%) MW:117.06 was synthesized following the procedure for example 2, using intermediate 49-4.
Synthesis example 14 preparation of intermediates 49-7
Figure BDA0002075109950000182
Intermediate 49-7(11.87g, 83%) MW:221.16 was synthesized according to the procedure for example 3 using intermediate 49-5.
Synthesis example 15 preparation of intermediates 49-8
Figure BDA0002075109950000183
Using intermediate 49-7, the procedure of example 4 was followed to give intermediate 49-8(11.45g, 90%) MW: 237.09.
Synthesis example 16 preparation of intermediates 49-9
Figure BDA0002075109950000191
Using intermediate 49-8, intermediate 49-9(9.84g, 93%) MW:219.07 was prepared according to the procedure for example 5.
Synthesis example 17 preparation of intermediates 49-11
Figure BDA0002075109950000192
Using intermediate 49-9 and intermediate 49-10, intermediate 49-11(14.66g, 79%) MW:413.08 was prepared according to the method of example 6.
Synthesis example 18 preparation of Compound 49
Figure BDA0002075109950000193
Compound 49(26.88g, 91%), MW: 832.38.
synthesis example 19 preparation of intermediates 58 to 11
Figure BDA0002075109950000201
Intermediate 58-11(10.81g, 81%) MW 297.24 was synthesized following the procedure for synthetic example 17, using bromobenzene instead of 49-10.
Synthesis example 20 preparation of Compound 58
Figure BDA0002075109950000202
Compound 58(24.58g, 91%), MW: 742.58.
synthesis example 21 preparation of intermediates 71-11
Figure BDA0002075109950000203
Intermediate 71-11(12.02g, 77%) MW:347.33 was synthesized using intermediate 71-10, following the procedure of example 17.
Synthesis example 22 preparation of Compound 71
Figure BDA0002075109950000211
Compound 71(23.13g, 90%), MW: 742.58.
synthesis example 23 preparation of intermediates 82-11
Figure BDA0002075109950000212
Intermediate 82-11(13.92g, 80%) MW 387.23 was synthesized using intermediate 82-10, following the procedure of example 17.
Synthesis example 24 preparation of Compound 82
Figure BDA0002075109950000213
Compound 82(34.23g, 90%), MW: 846.38.
synthesis example 25 Synthesis of intermediate 91-5
Figure BDA0002075109950000221
Intermediate 91-5(9.42g, 88%) MW:145.75 was synthesized following the procedure for synthetic example 2, using intermediate 91-4.
Synthesis example 26 preparation of intermediates 91-7
Figure BDA0002075109950000222
Intermediate 91-7(13.69g, 85%) MW 249.15 was synthesized according to the procedure for synthetic example 3 using intermediate 91-5.
Synthesis example 27 preparation of intermediates 91-8
Figure BDA0002075109950000223
Intermediate 91-8(13.11g, 90%) MW:265.15 was synthesized according to the procedure for the synthesis of example 4, using intermediate 91-7.
Synthesis example 28 preparation of intermediates 91-9
Figure BDA0002075109950000224
Using intermediate 91-8, intermediate 91-9(11.24g, 92%) MW:247.15 was synthesized according to the procedure for the synthesis of example 5.
Synthesis example 29 preparation of intermediates 91-11
Figure BDA0002075109950000231
Synthesis of intermediate 91-11(11.53g, 78%) MW:325.10 by the method of synthetic example 6 Using intermediate 91-9
Synthesis example 30 preparation of Compound 91
Figure BDA0002075109950000232
Compound 91(25.6g, 88%) MW 820.30 was synthesized according to the procedure for the synthesis of example 7, using intermediates 91-11 and 91-12.
Synthesis example 31 preparation of intermediates 108-11
Figure BDA0002075109950000233
Intermediate 108-11(13.65g, 80%) MW:375.20 was synthesized according to the procedure for the synthesis of example 29, using intermediate 2-bromonaphthalene.
Synthesis example 32 preparation of Compound 108
Figure BDA0002075109950000241
Compound 108(27.59g 90%), MW:842.70 was synthesized according to the procedure for the synthesis of example 7, using intermediates 108-11 and 108-12
Device example 1
Coating with a thickness of
Figure BDA0002075109950000242
The ITO glass substrate of (1) was washed in distilled water for 2 times, ultrasonically for 30 minutes, repeatedly washed in distilled water for 2 times, ultrasonically for 10 minutes, and after the washing with distilled water was completed, solvents such as isopropyl alcohol, acetone, and methanol were ultrasonically washed in this order, dried, transferred to a plasma cleaning machine, and the substrate was washed for 5 minutes and sent to an evaporation coater. 4,4' -tri [ 2-naphthyl phenylamino ] with the thickness of 50nm is evaporated on the prepared ITO transparent electrode]Triphenylamine (2-TNATA) as a hole injection layer. Then, compound 1 prepared in example 7 was vacuum-evaporated on the formed hole injection layer to form a hole transport layer having a thickness of 30 nm. However, the device is not suitable for use in a kitchenThen, 30nm thick blue host material 9, 10-di (2-naphthyl) Anthracene (AND) AND doping material N1, N1, N6, N6-tetraphenylpyrene-1, 6-diamine (TPPDA) were vapor-deposited on the hole transport layer. The weight ratio of host material to dopant material was 97: 3. Then, bis (2-methyl-8-hydroxyquinoline-N1) - (1, 1' -biphenyl-4-hydroxy) aluminum (BALq) as a hole-blocking layer was vacuum-deposited on the above light-emitting layer to a thickness of 10 nm. Alq3 was vacuum-deposited on the hole-blocking layer to a thickness of 40nm as an electron-transporting layer. Lithium fluoride (LiF) was vacuum-deposited on the electron transport layer to a thickness of 0.5nm as an electron injection layer. And finally, evaporating aluminum with the thickness of 150nm as a cathode, thereby completing the preparation of the organic electroluminescent device.
Device example 2
Device 2 was made according to the method of device example 1. Except that the hole transport material in device example 1 was changed to compound 11.
Device example 3
Device 3 was made according to the method of device example 1. Except that the hole transport material in device example 1 was changed to compound 13.
Device example 4
Device 4 was made according to the method of device example 1. Except that the hole transport material in device example 1 was changed to compound 21.
Device example 5
Device 5 was made according to the method of device example 1. Except that the hole transport material in device example 1 was changed to compound 28.
Device example 6
Device 6 was made according to the method of device example 1. Except that the hole transport material in device example 1 was changed to compound 49.
Device example 7
Device 7 was made according to the method of device example 1. Except that the hole transport material in device example 1 was changed to compound 58.
Device example 8
Device 8 was fabricated as in device example 1 except that the hole transport material in device example 1 was changed to compound 71.
Device example 9
Device 9 was made according to the method of device example 1. Except that the hole transport material in device example 1 was changed to compound 82.
Device example 10
Device 10 was made according to the method of device example 1. Except that the hole transport material in device example 1 was changed to compound 91.
Device example 11
Device 11 was made according to the method of device example 1. Except that the hole transport material in device example 1 was changed to compound 108.
Device control example 1: a device comparative example 1 was fabricated in the same manner as in device example 1, except that the material of the hole transport layer in device example 1 was changed to NPB.
The organic electroluminescent device prepared above was applied with a forward DC bias voltage, and the organic electroluminescent characteristics were measured by PR-650 photometric measuring equipment of Photo Research corporation at 5000cd/m2The life of T95 was measured using a life measuring device of McScience. The results are shown in the following table.
Figure BDA0002075109950000271
It can be seen from the above table that the organic electroluminescent device prepared by using the organic electroluminescent compound provided by the present invention as a hole transport layer has a lower start voltage, and the luminous efficiency and lifetime are significantly improved, compared to the organic electroluminescent device prepared by using NPB as a hole transport layer.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.

Claims (5)

1. An organic electroluminescent compound characterized by having any one of the following structures:
Figure FDA0002660127800000011
Figure FDA0002660127800000021
Figure FDA0002660127800000031
Figure FDA0002660127800000041
2. a method for producing the organic electroluminescent compound according to claim 1, comprising the steps of:
step 1: preparation of Compound 3
Placing the compound 1 and sodium tert-butoxide in toluene, adding the compound 2, a palladium acetate catalyst and BINAP under the protection of nitrogen, heating to 90 ℃ for reaction for 8 hours, after the reaction is finished, adding water for washing, extracting with ethyl acetate, drying an organic phase, and separating and purifying by a silica gel chromatographic column to obtain a compound 3;
step 2: preparation of Compound 5
Adding the compound 3 and the compound 4 into a mixed solvent of toluene and ethanol, then adding p-toluenesulfonic acid, carrying out reflux reaction for 12 hours, after the reaction is finished, adding water for washing, carrying out DCM extraction, drying an organic phase, and carrying out separation and purification by using a silica gel chromatographic column to obtain a compound 5;
and step 3: preparation of Compound 7
Putting the compound 5 and the compound 6 into DMF, adding anhydrous potassium carbonate, heating and stirring, adding copper oxide at 50 ℃, and heating to reflux reaction for 24 hours; after the reaction is finished, cooling to room temperature, filtering to remove redundant inorganic salt, adding a hydrochloric acid aqueous solution, heating to 60 ℃, stirring for reaction for 4 hours, cooling to room temperature, adding water for washing, extracting with ethyl acetate, drying an organic phase, and separating and purifying by using a silica gel chromatographic column to obtain a compound 7;
and 4, step 4: preparation of Compound 8
Dissolving the compound 7 in tetrahydrofuran, diluting sodium hypochlorite and sulfamic acid with water, adding the diluted sodium hypochlorite and sulfamic acid into a reactant, and heating and stirring for 4 hours; after the reaction is finished, cooling the temperature to normal temperature, and extracting with water and ethyl acetate to separate an organic layer; treating the organic layer with anhydrous magnesium sulfate, filtering, and concentrating under reduced pressure; recrystallizing the solid with ethyl acetate and petroleum ether to obtain a compound 8;
and 5: preparation of Compound 9
Placing the compound 8 in tetrahydrofuran, stirring, adding polyphosphoric acid, heating to 60 ℃, stirring for reacting for 12 hours, cooling to room temperature, washing with water, extracting with DCM, drying and concentrating an organic phase, and recrystallizing 1, 4-dioxane to obtain a compound 9;
step 6: preparation of Compound 11
Putting the compound 10 in tetrahydrofuran, cooling to-78 ℃, dropwise adding n-butyllithium, heating to room temperature for continuous reaction for 2 hours, cooling to-78 ℃ again, dropwise adding a tetrahydrofuran solution of the compound 9, then gradually heating to room temperature, and reacting for 16 hours; after the reaction is finished, quenching with dilute hydrochloric acid, extracting with ethyl acetate, drying an organic phase, and separating and purifying by using a silica gel chromatographic column to obtain a compound 11;
and 7: preparation of Compound represented by chemical formula 1
Putting the compound 11 and the compound 12 in tetrahydrofuran, adding methanesulfonic acid and polyphosphoric acid, reacting at normal temperature for 10 hours, after the reaction is finished, adding water for washing, extracting with ethyl acetate, drying an organic phase, and recrystallizing toluene to obtain a compound shown in a chemical formula 1;
the synthetic route is as follows:
Figure FDA0002660127800000061
wherein Z represents halogen, and the substituent groups and the number thereof on the chemical formula 1 correspond to those on each specific compound in claim 1.
3. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1.
4. The organic electroluminescent device according to claim 3, comprising a first electrode, a second electrode, and at least one organic layer between the first and second electrodes; the organic layer comprises at least one organic electroluminescent compound as claimed in claim 1.
5. The organic electroluminescent device according to claim 4, wherein the organic layer comprises at least a light-emitting layer and a hole-transporting layer, and at least one of the light-emitting layer and the hole-transporting layer comprises the organic electroluminescent compound according to claim 1.
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