CN112047918B - Organic electroluminescent material of heteroanthracene derivative containing naphthalene structure, preparation method and application - Google Patents

Organic electroluminescent material of heteroanthracene derivative containing naphthalene structure, preparation method and application Download PDF

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CN112047918B
CN112047918B CN202010947156.6A CN202010947156A CN112047918B CN 112047918 B CN112047918 B CN 112047918B CN 202010947156 A CN202010947156 A CN 202010947156A CN 112047918 B CN112047918 B CN 112047918B
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organic electroluminescent
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CN112047918A (en
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汪康
张雪
孙向南
敖日斯楞
徐佳楠
金成寿
马晓宇
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

The invention relates to a heteroanthracene derivative organic electroluminescent material containing a naphthalene structure, which has a chemical structural formula shown in formula I:
Figure DDA0002675712320000011
x, Y are independently selectedFrom chemical bonds, O, S, Si (R) 6 R 7 )，C(R 8 R 9 )，NR 10 (ii) a X and Y can not be chemical bonds at the same time; ring A, ring B are each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted C10-C30 fused ring group; R1-R5 are each independently selected from methyl, ethyl, propyl, isopropyl, tert-butyl, alkoxy, aryloxy, phenyl, biphenyl, or naphthyl; R6-R10 are each independently selected from methyl, ethyl, alkoxy, phenyl, naphthalene, anthracene, phenanthrene; ar (Ar) 1 、Ar 2 Each independently represents a substituted or unsubstituted C1-C30 alkyl group, a C6-C30 aryl group, a 3-to 30-membered heteroaryl group, a C10-C30 fused ring group, a C5-C30 spiro ring group; and the ring A and the ring B are both benzene. The material is applied to an organic electroluminescent device, can obviously reduce driving voltage, improves efficiency and prolongs service life.

Description

Naphthalene structure-containing heteroanthracene derivative organic electroluminescent material, and preparation method and application thereof
Technical Field
The invention relates to the technical field of luminescent materials, in particular to a heteroanthracene derivative organic electroluminescent material containing a naphthalene structure, a preparation method and application thereof, and an organic electroluminescent device taking the material as a luminescent auxiliary layer.
Background
The organic light emitting phenomenon is a phenomenon of converting electric energy into light energy using an organic substance. Organic electroluminescence (OLED) is a self-luminous device, which is advantageous in that it provides a wide viewing angle, a large contrast ratio, and a fast response time. An organic electric element utilizing an organic light emitting phenomenon generally has an anode, a cathode, and an organic layer structure disposed therebetween. In order to improve the efficiency and stability of organic electric devices, the organic layer is generally composed of a multilayer structure composed of various different substances, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. However, the hole transport layer material generally has a low Highest Occupied Molecular Orbital (HOMO) value, and excitons generated in the light emitting layer diffuse to the hole transport layer interface or the hole transport layer side, eventually causing light emission at the light emitting layer interface or charge imbalance in the light emitting layer, thereby emitting light at the hole transport layer interface, resulting in low color purity and efficiency of the organic electroluminescent device, and a short lifetime.
The efficiency, lifetime, driving voltage, and the like of the organic electroluminescent device are related to each other, and when the efficiency is increased, the driving voltage is relatively decreased, and crystallization of an organic substance by Joule heating (Joule heating) generated when the driving voltage is decreased and the driving is performed is decreased, and finally, the lifetime tends to be improved.
In recent years, in order to solve the problems of lifetime and efficiency of an organic electroluminescent device, a light-emitting auxiliary layer (a multi-layer hole transport layer) is generally added between a hole transport layer and a light-emitting layer. The light-emission auxiliary layer mainly functions as an auxiliary hole transport layer, and is therefore sometimes referred to as a second hole transport layer. The light-emitting auxiliary layer enables holes transferred from the anode to smoothly move to the light-emitting layer, and can block electrons transferred from the cathode so as to limit the electrons in the light-emitting layer, reduce a potential barrier between the hole transport layer and the light-emitting layer, reduce the driving voltage of the organic electroluminescent device, further increase the utilization rate of the holes, and improve the light-emitting efficiency and the service life of the device. In the conventional organic electroluminescent device (OLED), materials commonly used for the hole transport region mainly include copper phthalocyanine (CuPc), 4 '-bis [ N- (1-naphthyl) -N-phenylamino ] biphenyl (NPB), N' -diphenyl-N, N '-bis (3-methylphenyl) - (1, 1' -biphenyl) -4, 4 '-diamine (TPD), 4', 4 ″ -tris (3-methylphenylamino) triphenylamine (MTDATA), and the like. However, in the OLED using these materials, since the organic material used in the hole transport region has very high hole mobility, the hole-electron charge balance may be disrupted, resulting in a decrease in quantum efficiency (cd/a). In addition, when the OLED is driven at a high current, thermal stress occurs between the anode and the hole injection layer, which significantly reduces the lifespan of the device.
Disclosure of Invention
In view of the above technical problems, a first object of the present invention is to provide a heteroanthracene derivative organic electroluminescent material containing a naphthalene structure, so as to solve the problems of high driving voltage, low efficiency and short lifetime of the existing small molecule luminescent material.
In order to achieve the purpose, the invention adopts the following technical scheme.
The organic electroluminescent material of the heteroanthracene derivative containing a naphthalene structure has a chemical structural formula shown in a formula I:
Figure BDA0002675712310000021
x and Y are independently selected from chemical bond, O, S, Si (R) 6 R 7 )，C(R 8 R 9 )，NR 10 (ii) a X and Y can not be chemical bonds at the same time;
ring A, ring B are each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted C10-C30 fused ring group; ring a, ring B, are present simultaneously, or are absent simultaneously, or are present only one;
the positions of the substituents R1-R5 are any positions on the ring, and R1-R5 are independently selected from hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted C1-C30 alkoxy and substituted or unsubstituted C6-C30 aryloxy; or are linked to an adjacent substituent(s) to form a monocyclic or C3-C30 aliphatic or C6-C30 aromatic ring, the carbon atoms of which may be replaced by one or more heteroatoms selected from nitrogen, oxygen, sulfur and silicon;
R6-R10 are each independently selected from hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C10-C30 fused ring group;
l is a connecting bond, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted C10-C30 fused ring, substituted or unsubstituted C5-C30 spiro ring;
Ar 1 、Ar 2 the same or different, each independently represents substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted C10-C30 fused ring, substituted or unsubstituted C5-C30 spiro ring, or is linked to an adjacent substituent to form a monocyclic ring, or a C3-C30 aliphatic ring, or a C6-C30 aromatic ring, whose carbon atom may be replaced by one or more heteroatoms such as nitrogen, oxygen, sulfur, silicon, etc.
As preferred herein, R1-R5 are each independently selected from methyl, ethyl, propyl, isopropyl, tert-butyl, alkoxy, aryloxy, phenyl, biphenyl, or naphthyl; R6-R10 are each independently selected from methyl, ethyl, alkoxy, phenyl, naphthalene, anthracene, phenanthrene; ring A and ring B are both benzene.
As a further preferred aspect of the present invention, the light emitting material is selected from any one of the following structures:
Figure BDA0002675712310000031
Figure BDA0002675712310000041
Figure BDA0002675712310000051
Figure BDA0002675712310000061
the second purpose of the invention is to provide a preparation method of the organic electroluminescent material of the heteroanthracene derivative containing the naphthalene structure, which comprises the following steps:
the synthetic route is as follows:
Figure BDA0002675712310000071
the preparation method comprises the following steps:
step 1: adding reactant A and reactant B into a reaction vessel, dissolving in dry toluene, and adding Pd under nitrogen atmosphere 2 (dba) 3 、P(t-Bu) 3 t-BuONa; after addition, the reaction temperature was raised to 110 ℃, and the mixture was stirred for 10h, suction filtered using celite while hot to remove salts and catalyst, the filtrate was cooled to room temperature, then distilled water was added to the filtrate for washing, the organic phase was retained after liquid separation, the aqueous phase was extracted with ethyl acetate, the combined organic layers were dried over magnesium sulfate, and the solvent was removed using a rotary evaporator to obtain intermediate C;
step 2: n is a radical of 2 Under protection, the intermediate C, the reactant D, the tetrakis (triphenylphosphine) palladium and the potassium carbonate are respectively added into a reaction kettle in a volume ratio of 3: 1: 1, heating to 100 ℃ in a mixed solvent of toluene, ethanol and water, carrying out reflux reaction for 8 hours, cooling to room temperature after the reaction is finished, carrying out suction filtration after solid precipitation is finished, washing with water to remove salt, leaching with a small amount of ethanol, drying a filter cake, and putting the filter cake in 1, 4-dioxane for recrystallization to obtain an intermediate E;
and 3, step 3: n is a radical of hydrogen 2 Under protection, the intermediate E, the reactant F, the tetrakis (triphenylphosphine) palladium and the potassium carbonate are respectively added into a reaction kettle in a volume ratio of 3: 1: 1, heating to 110 ℃ in a mixed solvent of toluene, ethanol and water, carrying out reflux reaction for 8 hours, cooling to room temperature after the reaction is finished, carrying out suction filtration after solid precipitation is finished, washing with water to remove salt, leaching with ethanol, drying a filter cake, purifying residual substances by using a column chromatography, wherein the volume ratio of an eluent is ethyl acetate: petroleum ether 1:9 to give the compound of formula I.
The third purpose of the invention is to provide the application of the heteroanthracene derivative organic electroluminescent material containing the naphthalene structure shown in the formula I as a luminescent auxiliary layer material and a hole transport layer material in the field of manufacturing organic electroluminescent devices.
The fourth purpose of the present invention is to provide an organic electroluminescent device, which comprises an ITO glass substrate, a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a cathode layer, which are sequentially stacked from bottom to top, wherein the light-emitting auxiliary layer comprises the organic electroluminescent material shown in formula I.
Preferably, the hole injection layer is a compound mCP and F4-TCNQ with the thickness of 45nm, and the doping ratio of the mCP to the F4-TCNQ is 97: 3; the hole transport layer is a compound mCP with the thickness of 50nm, and the light-emitting auxiliary layer is an organic electroluminescent material with the thickness of 20nm and shown in a formula I; the luminescent layer is a host material CBP and a doping material (btfmp) with the thickness of 20nm 2 Ir (dbm), the weight ratio of the host material to the doping material is 95: 5; the hole blocking layer is BAlq with the thickness of 10 nm; the electron transport layer is Alq with a thickness of 40nm 3 (ii) a The electron injection layer is lithium fluoride with a thickness of 0.5 nm.
The invention has the advantages and beneficial effects that:
(1) the luminescent material provided by the invention combines two benzenes on the heteroanthracene, and the parent nucleus is connected with the naphthalene and then connected with the arylamine derivative, so that the spatial distortion degree of the whole compound is increased, and the luminescent material is more suitable for energy level collocation of an organic electroluminescent device.
(2) The luminescent material of the invention has simple preparation method, easily obtained raw materials, easily purified crude product and high-purity luminescent auxiliary material, and is suitable for industrial production.
(3) The organic electroluminescent device prepared by the luminescent material has greatly reduced driving voltage, obviously improved service life and efficiency, and the obvious effects on the performances enable the material to meet the condition of mass production.
Detailed Description
The technical solutions of the present application will be described clearly and completely in conjunction with the embodiments of the present application, and it is obvious that the described embodiments are only a part of the embodiments of the present application, and not all of the embodiments. All other embodiments obtained by a person of ordinary skill in the art based on the embodiments in the present application without making any creative effort belong to the protection scope of the present application.
The chemical structural formula of the heteroanthracene derivative organic electroluminescent material containing a naphthalene structure is shown as a formula I:
Figure BDA0002675712310000091
x and Y are independently selected from chemical bond, O, S, Si (R) 6 R 7 )，C(R 8 R 9 )，NR 10 (ii) a X and Y can not be chemical bonds at the same time;
ring A, ring B are each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted C10-C30 fused ring group; ring a, ring B, are present simultaneously, or are absent simultaneously, or are present only one;
the positions of the substituents R1-R5 are any positions on the ring, and R1-R5 are each independently selected from hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy; or are linked to an adjacent substituent(s) to form a monocyclic or C3-C30 aliphatic or C6-C30 aromatic ring, the carbon atoms of which may be replaced by one or more heteroatoms selected from nitrogen, oxygen, sulfur and silicon;
R6-R10 are each independently selected from hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C10-C30 fused ring;
l is a connecting bond, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted C10-C30 fused ring, substituted or unsubstituted C5-C30 spiro ring;
Ar 1 、Ar 2 the same or different, each independently represents substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted C10-C30 fused ring, substituted or unsubstituted C5-C30 spiro ring, or is linked to an adjacent substituent to form a monocyclic ring, or a C3-C30 aliphatic ring, or a C6-C30 aromatic ring, whose carbon atom may be replaced by one or more heteroatoms such as nitrogen, oxygen, sulfur, silicon, etc.
Further, R1-R5 are each independently selected from methyl, ethyl, propyl, isopropyl, tert-butyl, alkoxy, aryloxy, phenyl, biphenyl, or naphthyl; R6-R10 are each independently selected from methyl, ethyl, alkoxy, phenyl, naphthalene, anthracene, phenanthrene; ring A and ring B are both benzene.
In the above technical solutions, the term "substituted or unsubstituted" means substituted by one, two or more substituents selected from: deuterium; a halogen group; a nitrile group; a hydroxyl group; a carbonyl group; an ester group; a silyl group; a boron group; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted alkenyl; substituted or unsubstituted alkylamino; substituted or unsubstituted heterocyclylamino; substituted or unsubstituted arylamine; substituted or unsubstituted aryl; and a substituted or unsubstituted heterocyclic group, or a substituent in which two or more of the above-shown substituents are bonded, or no substituent. For example, "a substituent in which two or more substituents are linked" may include a biphenyl group. In other words, biphenyl can be an aryl group, or can be interpreted as a substituent with two phenyl groups attached.
EXAMPLE 1 Synthesis of Compound 1
The synthetic route is as follows:
Figure BDA0002675712310000101
the specific synthesis method comprises the following steps:
step 1: after adding reactant A-1(80mmol) and reactant B-1(88mmol) of the formula in 300ml of toluene in a reaction vessel, Pd was added under nitrogen atmosphere 2 (dba) 3 (0.88mmol)、P(t-Bu) 3 (4.4mmol), t-BuONa (240 mmol). After the addition, the reaction temperature was slowly (1 hour) warmed to 110 ℃ and the mixture was stirred for 10 h. The filtrate was cooled to room temperature, then distilled water was added to the filtrate to wash, the organic phase was retained after liquid separation, and the aqueous phase was extracted with ethyl acetate. The combined organic layers were then dried over magnesium sulfate and the solvent was removed using a rotary evaporator. Intermediate C-1(28.0g, 83% yield, Ms:421.22) was obtained.
Step 2: n is a radical of 2 Under protection, respectively adding the intermediate C-1(60mmol), the reactant D-1(66mmol), tetrakis (triphenylphosphine) palladium (0.6mmol) and potassium carbonate (132mmol) into a mixed solvent of 150mL of toluene, 50mL of ethanol and 50mL of water, heating to 100 ℃, refluxing for reaction for 8 hours, cooling to room temperature after the reaction is finished, after solid precipitation is finished, performing suction filtration, washing with water to remove salt, leaching with a small amount of ethanol, and drying a filter cake. Recrystallization from 1, 4-dioxane (240mL) gave intermediate E-1(28.0g, 87% yield, Ms: 537.22).
And step 3: n is a radical of 2 Under protection, respectively adding the intermediate E-1(45mmol), a reactant F-1(54mmol), tetrakis (triphenylphosphine) palladium (0.45mmol) and potassium carbonate (60mmol) into a mixed solvent of toluene (180mL), ethanol (60mL) and water (60mL), heating to 110 ℃, carrying out reflux reaction for 8 hours, cooling to room temperature after the reaction is finished, after solid precipitation is finished, carrying out suction filtration, washing with water to remove salt, carrying out leaching with ethanol, drying a filter cake, and purifying the rest substance by using a column chromatography, wherein the volume ratio of an eluent is ethyl acetate: petroleum ether 1:9 gave compound 1(28.2g, 76% yield, Ms: 825.40).
Note: the reaction F-1 was synthesized according to the method disclosed in J.org.chem.2017,82,4964-4969, CN 105968045A.
EXAMPLE 2 Synthesis of Compound 23
Figure BDA0002675712310000111
Step 1: after adding reactant A-23(80mmol) and reactant B-23(88mmol) of the formula in 300ml of toluene in a reaction vessel, Pd was added under nitrogen atmosphere 2 (dba) 3 (0.88mmol)、P(t-Bu) 3 (4.4mmol), t-BuONa (240 mmol). After the addition, the reaction temperature was slowly (1 hour) warmed to 110 ℃ and the mixture was stirred for 10 h. The filtrate was cooled to room temperature, then distilled water was added to the filtrate to wash, the organic phase was retained after liquid separation, and the aqueous phase was extracted with ethyl acetate. The combined organic layers were then dried over magnesium sulfate and the solvent was removed using a rotary evaporator. Intermediate C-23(35.9g, 86% yield, Ms:521.25) was obtained.
And 2, step: n is a radical of 2 Under protection, respectively adding the intermediate C-23(60mmol), the reactant D-23(66mmol), tetrakis (triphenylphosphine) palladium (0.6mmol) and potassium carbonate (132mmol) into a mixed solvent of 150mL of toluene, 50mL of ethanol and 50mL of water, heating to 100 ℃, carrying out reflux reaction for 8 hours, cooling to room temperature after the reaction is finished, after solid precipitation is finished, carrying out suction filtration, washing with water to remove salt, leaching with a small amount of ethanol, and drying a filter cake. Recrystallization from 1, 4-dioxane (240mL) gave intermediate E-23(30.6g, 80% yield, Ms: 637.12).
And step 3: n is a radical of 2 Under protection, respectively adding the intermediate E-23(45mmol), a reactant F-23(54mmol), tetrakis (triphenylphosphine) palladium (0.45mmol) and potassium carbonate (60mmol) into a mixed solvent of toluene (180mL), ethanol (60mL) and water (60mL), heating to 110 ℃, carrying out reflux reaction for 8 hours, cooling to room temperature after the reaction is finished, after solid precipitation is finished, carrying out suction filtration, washing with water to remove salt, carrying out leaching with ethanol, drying a filter cake, and purifying the rest substance by using a column chromatography, wherein the volume ratio of an eluent is ethyl acetate: petroleum ether 1:9 gave compound 23(29.1g, 71% yield, Ms: 911.41).
Note: reactant F-23 was synthesized according to the method disclosed in J.org.chem.2017,82,4964-4969, CN 105968045A.
EXAMPLE 3 Synthesis of Compound 30
Figure BDA0002675712310000121
Step 1: after adding reactant A-30(80mmol) and reactant B-30(88mmol) of the formula in 300ml of toluene in a reaction vessel, Pd was added under nitrogen atmosphere 2 (dba) 3 (0.88mmol)、P(t-Bu) 3 (4.4mmol), t-BuONa (240 mmol). After the addition, the reaction temperature was slowly (1 hour) warmed to 110 ℃ and the mixture was stirred for 10 h. The filtrate was cooled to room temperature, then distilled water was added to the filtrate to wash, the organic phase was retained after liquid separation, and the aqueous phase was extracted with ethyl acetate. The combined organic layers were then dried over magnesium sulfate and the solvent was removed using a rotary evaporator. Intermediate C-30(22.8g, 84% yield, Ms:339.14) was obtained.
And 2, step: n is a radical of 2 Under protection, respectively adding the intermediate C-30(60mmol), the reactant D-30(66mmol), tetrakis (triphenylphosphine) palladium (0.6mmol) and potassium carbonate (132mmol) into a mixed solvent of 150mL of toluene, 50mL of ethanol and 50mL of water, heating to 100 ℃, carrying out reflux reaction for 8 hours, cooling to room temperature after the reaction is finished, after solid precipitation is finished, carrying out suction filtration, washing with water to remove salt, leaching with a small amount of ethanol, and drying a filter cake. Recrystallization from 1, 4-dioxane (240mL) provided intermediate E-30(22.4g, 82% yield, Ms: 455.14).
And step 3: n is a radical of 2 Under protection, respectively adding the intermediate E-30(45mmol), the reactant F-30(54mmol), the tetrakis (triphenylphosphine) palladium (0.45mmol) and the potassium carbonate (60mmol) into a mixed solvent of toluene (180mL), ethanol (60mL) and water (60mL), heating to 110 ℃, carrying out reflux reaction for 8 hours, cooling to room temperature after the reaction is finished, after solid precipitation is finished, carrying out suction filtration, washing with water to remove the salt, carrying out leaching with ethanol, drying a filter cake, and purifying the rest substance by using a column chromatography, wherein the volume ratio of an eluent is ethyl acetate: petroleum ether 1:9 gave compound 30 (26).7g, 78% yield, Ms: 759.30).
Note: reactant F-30 was synthesized according to the method disclosed in J.org.chem.2017,82,4964-4969, CN 105968045A.
EXAMPLE 4 Synthesis of Compound 65
Figure BDA0002675712310000131
Step 1: after adding reactant A-65(80mmol) and reactant B-65(88mmol) of the formula in a reaction vessel and dissolving in 300ml of toluene, Pd was added under nitrogen atmosphere 2 (dba) 3 (0.88mmol)、P(t-Bu) 3 (4.4mmol), t-BuONa (240 mmol). After the addition, the reaction temperature was slowly (1 hour) warmed to 110 ℃ and the mixture was stirred for 10 h. The hot solution was filtered with celite by suction to remove salts and catalyst, the filtrate was cooled to room temperature, and then distilled water was added to the filtrate to wash, and after separation, the organic phase was retained and the aqueous phase was extracted with ethyl acetate. The combined organic layers were then dried over magnesium sulfate and the solvent was removed using a rotary evaporator. Intermediate C-65(27.2g, 81% yield, Ms:419.21) was obtained.
And 2, step: n is a radical of 2 Under protection, respectively adding the intermediate C-65(60mmol), the reactant D-65(66mmol), tetrakis (triphenylphosphine) palladium (0.6mmol) and potassium carbonate (132mmol) into a mixed solvent of 150mL of toluene, 50mL of ethanol and 50mL of water, heating to 100 ℃, carrying out reflux reaction for 8 hours, cooling to room temperature after the reaction is finished, after solid precipitation is finished, carrying out suction filtration, washing with water to remove salt, leaching with a small amount of ethanol, and drying a filter cake. Recrystallization from 1, 4-dioxane (240mL) provided intermediate E-65(27.3g, 85% yield, Ms: 535.45).
And 3, step 3: n is a radical of hydrogen 2 Under protection, respectively adding the intermediate E-65(45mmol), the reactant F-65(54mmol), the tetrakis (triphenylphosphine) palladium (0.45mmol) and the potassium carbonate (60mmol) into a mixed solvent of toluene (180mL), ethanol (60mL) and water (60mL), heating to 110 ℃, refluxing and reacting for 8 hours, cooling to room temperature after reaction is finished, after solid precipitation is finished, performing suction filtration, washing with water to remove salt, rinsing with ethanol, drying, filtering, drying and desaltingAnd purifying the residual substance by using column chromatography, wherein the eluent has the volume ratio of ethyl acetate: petroleum ether 1:9 gave compound 65(26.8g, 73% yield, Ms: 815.27).
Note: the reactant F-65 was synthesized according to the method disclosed in J.org.chem.2017,82,4964-4969, CN 105968045A.
EXAMPLE 5 Synthesis of Compound 75
Figure BDA0002675712310000141
Step 1: after adding reactant A-75(80mmol) and reactant B-75(88mmol) of the formula in a reaction vessel and dissolving in 300ml of toluene, Pd was added under nitrogen atmosphere 2 (dba) 3 (0.88mmol)、P(t-Bu) 3 (4.4mmol), t-BuONa (240 mmol). After the addition, the reaction temperature was slowly (1 hour) warmed to 110 ℃ and the mixture was stirred for 10 h. The filtrate was cooled to room temperature, then distilled water was added to the filtrate to wash, the organic phase was retained after liquid separation, and the aqueous phase was extracted with ethyl acetate. The combined organic layers were then dried over magnesium sulfate and the solvent was removed using a rotary evaporator. Intermediate C-75(27.9g, 84% yield, Ms:415.17) was obtained.
Step 2: n is a radical of 2 Under protection, respectively adding the intermediate C-75(60mmol), the reactant D-75(66mmol), tetrakis (triphenylphosphine) palladium (0.6mmol) and potassium carbonate (132mmol) into a mixed solvent of 150mL of toluene, 50mL of ethanol and 50mL of water, heating to 100 ℃, carrying out reflux reaction for 8 hours, cooling to room temperature after the reaction is finished, after solid precipitation is finished, carrying out suction filtration, washing with water to remove salt, leaching with a small amount of ethanol, and drying a filter cake. Recrystallization from 1, 4-dioxane (240mL) provided intermediate E-75(25.4g, 80% yield, Ms: 531.18).
And step 3: n is a radical of hydrogen 2 Under protection, respectively adding the intermediate E-75(45mmol), the reactant F-75(54mmol), the tetrakis (triphenylphosphine) palladium (0.45mmol) and potassium carbonate (60mmol) into a mixed solvent of toluene (180mL), ethanol (60mL) and water (60mL), heating to 110 ℃, refluxing and reacting for 8h, and reactingAfter the reaction is finished, cooling to room temperature, after the solid is separated out, performing suction filtration, washing with water to remove the salt, leaching with ethanol, drying a filter cake, and purifying the residual substance by using a column chromatography, wherein the volume ratio of an eluent is ethyl acetate: petroleum ether 1:9 gave compound 75(25.8g, 71% yield, Ms: 807.31).
Note: reactant F-75 was synthesized according to the method disclosed in J.org.chem.2017,82,4964-4969, CN 105968045A.
Examples 6 to 20
The synthesis of compounds 6, 12, 18, 25, 34, 40, 42, 45, 52, 68, 72, 78, 85, 88, 92 was carried out according to the synthesis methods of examples 1 to 5, the mass spectra and the molecular formulae are shown in table 1 below.
Table 1:
examples Compound (I) Molecular formula Theoretical value of mass spectrum Mass spectrometric test values
Example 6 6 C 56 H 41 NO 743.32 743.18
Example 7 12 C 58 H 43 NO 2 785.99 785.63
Example 8 18 C 59 H 41 NO 779.98 779.56
Example 9 25 C 62 H 51 NS 841.37 841.53
Example 10 34 C 57 H 41 NS 772.02 772.54
Example 11 40 C 72 H 47 NS 957.34 957.25
Example 12 42 C 59 H 41 NS 795.30 795.85
Example 13 45 C 58 H 43 NS 786.05 786.87
Example 14 52 C 54 H 35 NOS 745.24 745.35
Example 15 68 C 55 H 35 NS 3 805.19 805.13
Example 16 72 C 48 H 31 NS 2 685.90 685.44
Example 17 78 C 59 H 40 N 2 O 792.31 792.56
Example 18 85 C 52 H 33 NO 2 703.25 703.24
Example 19 88 C 66 H 53 NSi 888.24 888.32
Example 20 92 C 70 H 49 N 3 931.39 931.25
In addition, since other compounds of the present application can be obtained by referring to the synthetic methods of the above-mentioned examples, they are not illustrated here.
Example 21 fabrication of organic electroluminescent device containing Compound 1
The ITO glass substrate with the coating thickness of 150nm is placed in distilled water to be cleaned for 2 times, ultrasonic wave cleaning is carried out for 30 minutes, the ITO glass substrate is repeatedly cleaned for 2 times by the distilled water and is ultrasonically cleaned for 10 minutes, after the cleaning by the distilled water is finished, solvents such as isopropanol, acetone, methanol and the like are sequentially ultrasonically cleaned and are dried, the ITO glass substrate is transferred into a plasma cleaning machine, the ITO glass substrate is cleaned for 5 minutes, and the ITO glass substrate is sent into an evaporation machine.
The prepared ITO transparent electrode was vapor-deposited with compounds mCP and F4-TCNQ (doping ratio 97:3) as hole injection layers to a thickness of 45 nm. Then, a hole transport layer having a thickness of 50nm was vacuum-deposited on the formed hole injection layer using the compound mCP. Evaporating the compound 1 with the thickness of 20nm on the hole transport layer to be used as a luminescence auxiliary layer;
then, a host material CBP and a dopant material (btfmp) were vapor-deposited on the luminescence auxiliary layer to a thickness of 20nm 2 Ir(dbm). The weight ratio of host material to dopant material was 95: 5. Then, BAlq with a thickness of 10nm as a hole blocking layer and an electron transport layer Alq with a thickness of 40nm were vacuum-deposited on the light-emitting layer 3 . 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.
The chemical structural formula of the raw materials is as follows:
Figure BDA0002675712310000161
example 22 example 40
In the same manner as in the other examples except for replacing compound 1 in example 21 with compounds 6, 12, 18, 23, 25, 30, 34, 40, 42, 45, 52, 65, 68, 72, 75, 78, 85, 88 and 92, organic electroluminescent devices containing compounds 6, 12, 18, 23, 25, 30, 34, 40, 42, 45, 52, 65, 68, 72, 75, 78, 85, 88 and 92 were produced.
Comparative example 1
An organic electroluminescent device containing comparative compound 1 was fabricated. An organic electroluminescent device containing comparative compound 1 was produced in the same manner as in example 21 except that compound 1 of the luminescence auxiliary layer was replaced with comparative compound 1.
Figure BDA0002675712310000162
Comparative example 2
An organic electroluminescent device containing comparative compound 2 was fabricated. An organic electroluminescent device containing comparative compound 2 was fabricated in the same manner as in example 21 except that compound 1 of the luminescence auxiliary layer was replaced with comparative compound 2.
Figure BDA0002675712310000171
Comparative example 3
Comparative example 3 was prepared according to the method of example 21, except that the luminescence auxiliary layer was not included.
Table 2 shows the results of the tests of the light emitting characteristics of the devices of examples 21 to 40 of the present invention and the devices of comparative examples 1 to 3 (luminance value of 5000 cd/m) 2 )。
Examples Luminescence auxiliary layer compound Voltage (V) Efficiency (cd/A) Life (T95)
Comparative example 1 Comparative Compound 1 5.8 25.1 104
Comparative example 2 Comparative Compound 2 5.1 32.9 128
Comparative example 3 ---- 6.4 17.6 84
Example 21 1 3.8 40.1 149
Example 22 6 4.0 41.4 154
Example 23 12 4.1 37.9 135
Example 24 18 3.9 40.2 152
Example 25 23 3.8 38.9 142
Example 26 25 3.7 36.7 138
Example 27 30 3.6 37.8 145
Example 28 34 4.0 38.6 147
Example 29 40 4.2 41.0 156
Example 30 42 3.9 34.9 132
Example 31 45 3.8 37.4 139
Example 32 52 4.1 39.7 146
Example 33 65 3.7 40.0 154
Example 34 68 3.6 41.7 143
Example 35 72 3.8 35.5 140
Example 36 75 3.9 36.9 144
Example 37 78 4.1 40.3 152
Example 38 85 4.0 37.3 141
Example 39 88 3.7 38.4 148
Example 40 92 3.9 39.5 152
As can be seen from Table 2, the organic electroluminescent devices prepared using the compounds provided by the present invention as the material of the luminescence auxiliary layer are significantly improved in driving voltage, luminous efficiency and life as compared to the organic electroluminescent devices using the comparative compounds 1 to 2 as the material of the luminescence auxiliary layer and not using the luminescence auxiliary layer.
The device data shows that compared with a comparative compound 2 with a similar structure, the luminescent auxiliary compound has the advantages that the driving voltage, the luminescent efficiency and the service life are obviously improved, the difference is probably that the side chain connected with the mother nucleus is different, and the mother nucleus is connected with the naphthalene and then connected with the arylamine derivative, so that the space distortion degree of the whole compound is increased, and the luminescent auxiliary compound is more suitable for the energy level collocation of the device. Compared with the comparative compound 2, the driving voltage is reduced by 0.9-1.5V, the luminous efficiency is improved by about 9.8-16.6%, and the service life of the device is prolonged by about 4-28 h. Compared with the comparative compound 1, the driving voltage is reduced by 1.6-2.2V, the luminous efficiency is improved by about 2-8.8%, and the service life of the device is improved by about 28-52 h.
It will be apparent to those skilled in the art that many modifications and variations can be made in the present invention without departing from the spirit and scope of the invention. It is therefore contemplated that the present invention cover the modifications and variations of this invention provided they come within the scope of the appended claims and their equivalents.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.

Claims (4)

1. The organic electroluminescent material of the heteroanthracene derivative containing a naphthalene structure is characterized in that the luminescent material is selected from any one of the following structures:
Figure FDA0003741704470000011
2. the use of the heteroanthracene derivative organic electroluminescent material of claim 1, which contains a naphthalene structure, as a luminescence auxiliary layer in the field of the production of organic electroluminescent devices.
3. An organic electroluminescent device, which comprises an ITO glass substrate, a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a cathode layer which are sequentially stacked from bottom to top, and is characterized in that the light-emitting auxiliary layer comprises the organic electroluminescent material as claimed in claim 1.
4. An organic electroluminescent device according to claim 3, wherein the hole injection layer is a 45nm thick compound mCP and F4-TCNQ, the mCP to F4-TCNQ doping ratio is 97: 3; the hole transport layer is a compound mCP with a thickness of 50nm, and the luminescence auxiliary layer is the organic electroluminescent material described in claim 1 with a thickness of 20 nm; the luminescent layer is a host material CBP and a doping material (btfmp) with a thickness of 20nm 2 Ir (acac), wherein the weight ratio of the main material to the doping material is 95: 5; the hole blocking layer is BAlq with the thickness of 10 nm; the electron transport layer is Alq with the thickness of 40nm 3 (ii) a What is neededThe electron injection layer is lithium fluoride with the thickness of 0.5 nm;
the chemical structural formula of the raw materials is as follows:
Figure FDA0003741704470000021
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