TWI630260B - Quinoline-substituted diphenylpyrimidines compounds and organic electroluminescent devices using the same - Google Patents

Abstract

A quinoline-substituted diphenylpyrimidine compound having the structure of the formula (I) and an organic electroluminescent device using the same, wherein X ₁ , A ₁ and n are as defined in the specification.

Description

Quinoline substituted diphenylpyrimidine compound and organic electroluminescent device thereof

The present invention relates to a material for an organic electroluminescent device and an organic electroluminescent device using the same, and more particularly to a material which can increase the efficiency of the device and prolong the life of the organic electroluminescent device and the organic device using the material. Excitation light element.

Recently, organic electroluminescent devices (OLEDs) have commercial advantages due to their long life, high efficiency, low driving voltage, wide color gamut, and low cost on high-luminance high-density pixel displays. It satisfies the application of the organic electroluminescent device, with particular emphasis on the development of its novel organic materials.

A typical OLED is sandwiched between at least one organic emissive layer between the anode and the cathode. When a current is applied, the anode is injected into the hole and the cathode injects electrons into the one or more organic light-emitting layers, and the injected holes and electrons each migrate to the opposite charged electrode. When electrons and holes are confined to the same molecule, an "exciton" is formed, which has a localized electron-hole pair excited by an excited energy state, which is excited by a luminescence mechanism. The child relaxes and emits light. In order to improve the charge transport capability and luminous efficiency of such components, one or more additional layers, such as an electron transport layer and/or a hole transport layer, or an electron blocking layer and/or a hole blocking layer, are bonded adjacent to the light emitting layer. . In the literature, it has been well documented that the host material is blended with another guest material to enhance device performance and adjust color. Several OLED materials and device configurations are described in U.S. Patent Nos. 4,769,292, 5,844,363, 5,707,745, 6,,,,,, 6,昱Ray Optoelectronics Technology has applied for in 2016 and was awarded the Republic of China Patent No. I582081 in 2017. The electronic transmission materials introduced in this patent have certain novelty and effect, and the effect of this new patent application is better than the previous case. .

The reason for manufacturing a multi-layer thin film structure OLED includes the stability of the interface between the electrodes and the organic layer and the combination of organic materials. In organic materials, the mobility of electrons and holes is significantly different. If a so-called hole transmission and electron transport layer is used, holes and electrons can be efficiently transmitted to the emissive layer, so that the emissive layer The density of electrons and holes is balanced to increase luminous efficiency. Properly combining the above organic layers enhances the efficiency and longevity of the component. However, it is still difficult to find organic materials that meet the needs of all practical display applications, especially organic materials for vehicle displays or illumination sources, which are required to have high temperature resistance and long life.

Therefore, there is a need for an organic material that can significantly improve the lifetime of the organic electroluminescent device, improve carrier mobility, and good heat resistance to meet the needs of diverse applications.

The object of the present invention is to provide a long life and high carrier A material for organic electroluminescent elements that has good mobility and heat resistance.

The present invention provides a quinoline substituted diphenylpyrimidine compound having the structure of formula (I):

Wherein X ₁ represents a substituted or unsubstituted C _6-30 aryl group, substituted or unsubstituted C _5-30 containing at least one hetero atom selected from the group consisting of N, O, and S; a heteroaryl group; A ₁ represents a substituted or unsubstituted C _6-36 aryl group, substituted or unsubstituted C ₅ containing at least one hetero atom selected from the group consisting of N, O, and S; _{-30heteroaryl} ; X ₁ and A ₁ are the same or different, and at least one of them is substituted or unsubstituted, and contains at least one hetero atom selected from the group consisting of N, O, and S. _{5-30heteroaryl} ; and n represents an integer of 1 or 2, and when n represents 2, each of A ₁ is the same or different.

The present invention provides an organic electroluminescent device comprising: a cathode; an anode; and an organic layer interposed between the cathode and the anode, and the organic layer comprises a quinoline substitution of the structure of the formula (I) of the present invention Diphenylpyrimidine compound.

According to the present invention, the quinoline having the structure of formula (I) provided by the present invention The substituted diphenylpyrimidine compound can improve the life of the organic electroluminescent device, improve carrier mobility, and provide good heat resistance.

100, 200, 300‧‧‧ Organic electroluminescent components

110, 210, 310‧‧‧ substrates

120, 220, 320‧‧‧ anode

130, 230, 330‧‧‧ hole injection layer

140, 240, 340‧‧‧ hole transport layer

150, 250, 350‧‧ ‧ luminescent layer

160, 260, 360‧‧‧ electron transport layer

170, 270, 370‧‧‧ electron injection layer

180, 280, 380‧‧‧ cathode

245, 355‧‧ ‧ exciton blocking layer

Embodiments of the present invention are described with reference to the accompanying drawings in which: FIG. 1 is a schematic cross-sectional view showing an embodiment of an organic electroluminescent device of the present invention; and FIG. 2 is another embodiment of the organic electroluminescent device of the present invention. BRIEF DESCRIPTION OF THE DRAWINGS FIG. 3 is a schematic cross-sectional view showing still another embodiment of the organic electroluminescent device of the present invention.

The embodiments of the present invention are described by way of specific examples, and those skilled in the art can readily understand the advantages and functions of the present invention from the disclosure. The present invention may be embodied or applied by other different embodiments, and the various details of the present invention may be variously modified and changed without departing from the spirit and scope of the invention. In addition, all ranges and values herein are inclusive and combinable. Any value or point falling within the ranges recited herein, such as any integer, may be the minimum or maximum value to derive the lower range and the like.

According to the invention, a quinoline substituted diphenylpyrimidine compound having the structure of formula (I):

Wherein X ₁ represents a substituted or unsubstituted C _6-30 aryl group, substituted or unsubstituted C _5-30 containing at least one hetero atom selected from the group consisting of N, O, and S; a heteroaryl group; A ₁ represents a substituted or unsubstituted C _6-36 aryl group, substituted or unsubstituted C ₅ containing at least one hetero atom selected from the group consisting of N, O, and S; _{-30heteroaryl} ; X ₁ and A ₁ are the same or different, and at least one of them is substituted or unsubstituted, and contains at least one hetero atom selected from the group consisting of N, O, and S. _{5-30heteroaryl} ; and n represents an integer of 1 or 2, and when n represents 2, each of A ₁ is the same or different.

In a specific embodiment, the quinoline-substituted diphenylpyrimidine compound having the structure of the formula (I) is represented by the structure of the formula (I-1) or the structure of the formula (I-2): Wherein X ₁ represents a substituted or unsubstituted C _6-30 aryl group, substituted or unsubstituted C _5-30 containing at least one hetero atom selected from the group consisting of N, O, and S; a heteroaryl group; A ₁ represents a substituted or unsubstituted C _6-36 aryl group, substituted or unsubstituted C ₅ containing at least one hetero atom selected from the group consisting of N, O, and S; _{-30heteroaryl} ; X ₁ and A ₁ are the same or different, and at least one of them is substituted or unsubstituted, and contains at least one hetero atom selected from the group consisting of N, O, and S. _{5-30heteroaryl} ; and n represents an integer of 1 or 2, and when n represents 2, each of A ₁ is the same or different.

The A ₁ of the quinoline-substituted diphenylpyrimidine compound having the structure of the formula (I) is a substituted or unsubstituted C _6-36 aryl group, and the substituted or unsubstituted one is selected from N, O. And the C _5-30 heteroaryl group of at least one hetero atom in the group consisting of S, because the planar structure is more, it can contribute to molecular stacking and increase the transport effect of the carrier, but it is selected The carbon number of the group should not be too much to avoid unnecessary crystallization.

The X ₁ of the quinoline-substituted diphenylpyrimidine compound having the structure of the formula (I) is a substituted or unsubstituted C _6-30 aryl group, and the substituted or unsubstituted one is selected from N, O. And a C _5-30 heteroaryl group of at least one hetero atom in the group consisting of S, which has the effect of inhibiting molecular crystallization. In one embodiment, X ₁ is pyridyl, quinolinyl or naphthyl.

In another embodiment, the quinoline-substituted diphenylpyrimidine compound having the structure of formula (I), X ₁ is selected from the group consisting of: Wherein Xr represents hydrogen, fluorine, cyano, C _1-4 alkyl or unsubstituted C _6-18 aryl.

In a specific embodiment, the A ₁ is selected from one of the following groups: Wherein L represents O or S; Ar ₁ to Ar ₆ each independently represent hydrogen, unsubstituted C _6-18 aryl; and R ₁ to R ₄ each independently represent hydrogen, substituted or unsubstituted C _6-12 The aryl group, R ₁ and R ₂ together with the attached carbon atom form a C _6-18 fused aromatic ring system or R ₃ and R ₄ together with the attached carbon atom form a C _6-18 fused aromatic ring system; One of Y ₁ and Y ₂ is a single bond and is attached to the compound of formula (I), the other being hydrogen.

In one embodiment, when n is 1, the compound of formula (I) is represented by formula (I-3) or formula (I-4):

In a specific embodiment, when n is 2, the compound of the formula (I) is represented by the formula (I-5):

In another specific embodiment, when n is 2, the A ₁ is the same structure.

As used herein, "substituted" in "substituted or unsubstituted" means that a hydrogen atom in a functional group is replaced by another atom or group (ie, a substituent). The substituents are each independently selected from at least one of the group consisting of hydrazine, halogen, C _1-30 alkyl, C _1-30 alkoxy, C _6-30 aryl, C _{5- 30} heteroaryl, C _5-30 heteroaryl substituted by C _6-30 aryl, benzimidazolyl, C _3-30 cycloalkyl, C _5-7 heterocycloalkyl, tri C _1-30 alkane Base alkyl, tri-C _1-30 aryl decyl, di C _1-30 alkyl C _6-30 aryl decyl, C _1-30 alkyl di C _6-30 aryl decyl, C _2-30 Alkenyl, C _2-30 alkynyl, cyano, di C _1-30 alkylamino, di C _6-30 aryl boron, di C _1-30 alkyl boron, C _1-30 alkyl, C _6-30 aryl C _1-30 alkyl, C _1-30 alkyl C _6-30 aryl, carboxyl, nitro and hydroxy.

As used herein, "aryl" means aryl or (extended) aryl, which means a monocyclic or fused ring derived from an aromatic hydrocarbon, and includes phenyl, biphenyl, triphenyl, naphthalene. , dinaphthyl, phenylnaphthyl, naphthylphenyl, anthracenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, phenylphenanyl, anthracenyl, fluorenyl, hydrazine Triphenyl, fluorenyl, fused tetraphenyl, anthracenyl, fluorenyl, naphtylnaphthyl, propadienyl fluorenyl and the like.

Herein, "heteroaryl" means a heteroaryl group or a (hetero)heteroaryl group, and the heteroaryl group means a ring main chain atom containing at least one hetero atom selected from the group consisting of N, O, and S. An aryl group which may be a monocyclic ring such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, iso Azolyl, Azolyl, Diazolyl, three Base, four Base, triazolyl, tetrazolyl, furazolyl, pyridyl, pyridyl Base, pyrimidinyl, oxime a condensed ring condensed with at least one benzene ring, such as a benzofuranyl group, a benzothienyl group, an isobenzofuranyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzimidazolyl group, Benzothiazolyl, benzisothiazolyl, benzoid Azolyl, quinolyl, isoquinolyl, porphyrinyl, quinazolinyl, quin Orolinyl, carbazolyl, brown Azolyl, phenanthryl, benzodiazepine Mercapto, dihydroacridinyl and the like.

In a specific embodiment, the preferred embodiment of the quinoline-substituted diphenylpyrimidine compound having the structure of the formula (I) is selected from Table 1, but is not limited thereto.

In another embodiment, the quinoline-substituted diphenylpyrimidine compound having the structure of the formula (I) is one of the compound (1-10) or the compound (1-11):

The quinoline-substituted diphenylpyrimidine compound having the structure of the formula (I) of the present invention preferably has a glass transition temperature of from 98 to 165 ° C, particularly preferably a glass transition temperature of from 140 to 165 ° C. It can withstand the long-term high temperature inside the car, so it is suitable for organic electroluminescent components of automotive displays.

The present invention provides an organic electroluminescent device comprising: a cathode; an anode; and an organic layer interposed between the cathode and the anode, and the organic layer comprises a quinoline substitution of the structure of the formula (I) of the present invention Diphenylpyrimidine compound.

The organic layer of the organic electroluminescent device of the present invention may be an electron transport layer, an electron injection layer, a light emitting layer, a hole blocking layer or an electron blocking layer, and in addition to the organic layer, the organic electroluminescent device is reconfigurable And comprising at least one layer selected from the group consisting of an electron transport layer, an electron injection layer, a light emitting layer, a hole blocking layer and an electron blocking layer, wherein the light emitting layer further comprises a fluorescent or phosphorescent dopant, And a host material corresponding to the fluorescent or phosphorescent dopant, respectively.

In one embodiment, the organic layer comprising the quinoline-substituted diphenylpyrimidine compound of the formula (I) of the present invention is preferably an electron transport layer and has a thickness of from 20 nm to 30 nm. Wherein the electron transport layer can be a quinoline-substituted diphenylpyrimidine compound having the structure of the formula (I) as a single material, or a quinoline-substituted diphenylpyrimidine compound having the structure of the formula (I); Used in conjunction with electrically conductive dopants.

In another embodiment, the electron transport layer further comprises an N-type electrically conductive dopant, wherein the N-type electrically conductive dopant is substituted with the quinoline substituted structure of the formula (I) of the present invention. Phenylpyrimidine compound produces chelation (chelation), which can make electrons more easily injected from the cathode into the electron transport layer, and solves the problem of phase separation and formation of quenching center caused by poor compatibility of metal and electron transport host materials in the prior art, and is effective. The electron transport efficiency of the electron transport layer is improved.

The N-type electrically conductive dopant system applied to the electron transport layer may be a nitrate, carbonate, phosphate or quinoline salt of an organic alkali metal/alkaline earth metal. Specifically, such as lithium carbonate, lithium quinolate (Liq), lithium azide, barium carbonate, silver nitrate, barium nitrate, magnesium nitrate, zinc nitrate, barium nitrate, barium carbonate, barium fluoride , azide, etc., wherein the N-type electrically conductive dopant is preferably lithium quinolate.

In one embodiment, the N-type electrically conductive dopant is present in an amount of from 5% by weight to 50% by weight based on the weight of the electron transporting layer.

The structure of the organic electroluminescent device of the present invention will be described with reference to the drawings.

BRIEF DESCRIPTION OF THE DRAWINGS Figure 1 is a schematic cross-sectional view showing one embodiment of an organic electroluminescent device of the present invention. The organic electroluminescent device 100 includes a substrate 110, an anode 120, a hole injection layer 130, a hole transport layer 140, a light-emitting layer 150, an electron transport layer 160, an electron injection layer 170, and a cathode 180. The organic electroluminescent device 100 can be fabricated by sequentially depositing the above layers.

Fig. 2 is a schematic cross-sectional view showing another embodiment of the organic electroluminescent device of the present invention. The organic electroluminescent device 200 includes a substrate 210, an anode 220, a hole injection layer 230, a hole transport layer 240, an exciton blocking layer 245, a light emitting layer 250, an electron transport layer 260, an electron injection layer 270, and a cathode 280, and The difference between the figures is that the exciton blocking layer 245 is electrically connected. The hole transport layer 240 is between the light emitting layer 250.

Figure 3 is a schematic cross-sectional view showing still another embodiment of the organic electroluminescent device of the present invention. The organic electroluminescent device 300 includes a substrate 310, an anode 320, a hole injection layer 330, a hole transport layer 340, a light-emitting layer 350, an exciton blocking layer 355, an electron transport layer 360, an electron injection layer 370, and a cathode 380, and The difference in FIG. 1 is that the exciton blocking layer 355 is disposed between the light emitting layer 350 and the electron transport layer 360.

The organic electroluminescent device can be fabricated in accordance with the reverse structure of the elements shown in FIGS. 1 to 3. One or more layers are added or removed as needed for such inverted structures.

The material of the hole injection layer, the hole transport layer, the exciton blocking layer, the electron blocking layer, and the electron injection layer may be selected from conventional materials. For example, the electron transporting material forming the electron transporting layer is different from the material of the light emitting layer. And it has hole transportability, thereby facilitating migration of holes in the electron transport layer, and preventing carrier accumulation due to dissociation energy difference between the light-emitting layer and the electron transport layer.

The quinoline-substituted diphenylpyrimidine compound of the formula (I) of the present invention is used for an electron transport layer, and has a triplet energy (E _T ) higher than 2.2 eV and good carrier mobility, which is helpful. The exciter is lifted in the luminescent layer to emit light.

In addition, U.S. Patent No. 20170005275A1 exemplifies that a p-type doped hole transport layer is doped with HT-D2 in HT3, the entire contents of which are cited in the present application, and the patent also uses Lithium quinolate (Liq) as n Type doping material to be doped in electron transport material (ET3), its full content It is cited for the present invention. The entire contents of the cathodes as exemplified in U.S. Patent Nos. 5, 573, 436 and 5, 707, 745, which are incorporated herein by reference in their entirety, the disclosures of ITO Layer. The application and principles of the various barrier layers disclosed in U.S. Patent Nos. 6,097,147 and 2,030, 030, 980 are incorporated herein by reference. The injection layer exemplified in U.S. Patent No. 2,040,174,116 and the protective layer described in the same application are hereby incorporated by reference.

Structures and materials that are not specifically described are also applicable to the present invention. Organic electroluminescent elements comprising polymeric materials (PLEDs) are disclosed in U.S. Patent No. 5,247,190, the entire disclosure of which is incorporated herein by reference. Further, an organic electroluminescent device having a single organic layer or an organic electroluminescent device formed by stacking as disclosed in U.S. Patent No. 5,707,745, the entire disclosure of which is incorporated herein.

Unless otherwise specified, any of the various embodiments may be deposited using any suitable method. In the case of the organic layer, the preferred method comprises the thermal evaporation method and the printing method as disclosed in U.S. Patent Nos. 6,013,982 and 6,087,196, the entire disclosure of which is incorporated herein by reference. Organic vapor phase deposition (OVPD), the entire disclosure of which is incorporated herein by reference. U.S. Patent No. 10/233,470, the disclosure of which is incorporated herein by reference. The invention is cited. Other suitable methods include spin coating and solution based processes. The solution based process is preferably carried out in a nitrogen or inert gas atmosphere. For other layers, the preferred method involves thermal evaporation. Preferred pattern The process includes a process for re-cold deposition by mask deposition as disclosed in U.S. Patent Nos. 6,294,398 and 6,468,819, and a process for integrated printing or organic vapor deposition deposition and patterning, the entire contents of which are incorporated herein by reference. Of course, other methods can also be used. The material used for deposition can be adjusted to correspond to the deposition method it is used for.

The quinoline-substituted diphenylpyrimidine compound having the structure of the formula (I) of the present invention can be formed into an amorphous thin film applied to an organic electroluminescent device by vacuum deposition or wet coating. When the compound is used in any of the above organic layers, it exhibits a long service life and good thermal stability.

The organic electroluminescent device of the present invention can be applied to a single component, and its structure is an array configuration or an element having an anode and a cathode in the X-Y coordinate of the array. Compared with the conventional components, the present invention can significantly improve the service life and driving stability of the organic electroluminescent device. In addition, in combination with the phosphorescent dopant in the light-emitting layer, the organic electroluminescent device of the present invention can be applied to a full-color or colorful display panel to achieve better performance and emit white light.

The nature and efficacy of the present invention are described in detail below by way of examples. The detailed description is merely illustrative of the nature of the invention, and the invention is not limited to the specific embodiments.

Synthesis Example 1: Synthesis of Compound 1-1

4-Bromoacetophenone (10 g, 50.23 mmole) and quinolin-8-ylboronic acid (9.12 g, 52.75 mmole) were placed in a reaction tank, and 120 ml was added. Toluene, and potassium carbonate (18.05 g, 130.6 mmole) was dissolved in 70 ml of deionized water and added to the reaction tank while adding tetrakis(triphenylphosphine)palladium (Pd(PPh ₃ ) ₄ ) (1.74 g, 1.507). Mmmol) and 30 ml of ethanol, and heated and stirred, heated to 80 ° C and reacted overnight. After the reaction was completed, 300 ml of deionized water was added. After stirring for 30 minutes, the stirring was stopped and allowed to stand for stratification. After removing the aqueous layer, it was purified by silica gel chromatography, concentrated to a thick state, and then 300 ml was added. The hexane was precipitated and the organic layer was combined and filtered to give a pale yellow solid A (~8 g).

The pale yellow solid A (10 g, 40.737 mmole) and 4-bromobenzaldehyde (8.23 g, 44.48 mmole) were placed in a reaction tank, and after thoroughly removing water, 230 ml of ethanol was added to start stirring. Sodium methoxide (0.655 g, 12.31 mmole) was added and stirred at room temperature for 16 h. Thereafter, 3-Amidinopyridinium chloride (6.7 g, 44.34 mmole) and sodium hydroxide (3.22 g, 80.61 mmole) were added, and 30 ml of toluene was added thereto, and the heating device was turned on. Heat to 75 ° C and react overnight. After the reaction is completed, the solid is collected by filtration, and then 250 ml of toluene is added. The mixture was heated to stir and the solid was filtered to give a white solid B (about 5.5 g).

The milky white solid B (10 g, 19.40 mmole) and 4-dibenzofuran boronic acid (dibenzo[b,d]furan-4-ylboronic acid) (4.936 g, 23.38 mmole) were placed in a reaction tank, and 120 ml was added. Toluene. Potassium carbonate (9.384 g, 67.9 mmole) was dissolved in 70 ml of deionized water and added to the reaction tank, and tetrakis(triphenylphosphine)palladium (Pd(PPh ₃ ) ₄ ) (1.12 g, 0.97 mmole) and 30 ml were added. The ethanol was heated and stirred, heated to 80 ° C and reacted overnight. After the reaction was completed, 300 ml of deionized water was added, stirred for 30 minutes, the stirring was stopped, and the mixture was allowed to stand for stratification, filtered, and the crude product was received using a Soxhlet extractor, and the tannin extract was used for chromatography. Purification, concentration to a thick state, EtOAc (3 mL), EtOAc (EtOAc)

Compound 1-1 ¹ H NMR: ¹ H NMR (CDCl ₃ , 400 MHz), δ 10-9.9 (S, 1H); 9.02-8.99 (m, 2H); 8.85-8.82 (d, 1H); 8.45-8.26 (m) , 5H); 8.2-7.45 (m, 17H).

Synthesis Example 2: Synthesis of Compound 1-2

The reactant A (10 g, 40.737 mmole) and 3-bromobenzaldehyde (8.23 g, 44.48 mmole) were placed in a reaction tank, and after thoroughly removing water, 230 ml of ethanol was added, stirring was started, and methanol was added. Sodium (0.655 g, 12.31 mmole) was stirred at room temperature for 16 h. Thereafter, 3-Amidinopyridinium chloride (6.7 g, 44.34 mmole) and sodium hydroxide (3.22 g, 80.61 mmole) were added, and 30 ml of toluene was added thereto, and the heating device was turned on. Heat to 75 ° C and react overnight. After completion of the reaction, the solid was filtered, and then stirred and stirred with 250 ml of toluene, and the solid was filtered to give a white solid C (about 5 g).

The milky white solid C (10 g, 19.40 mmole) and 4-dibenzofuran boronic acid (dibenzo[b,d]furan-4-ylboronic acid) (4.936 g, 23.38 mmole) were placed in a reaction tank, and 120 ml was added. Toluene. Potassium carbonate (9.384 g, 67.9 mmole) was dissolved in 70 ml of deionized water and added to the reaction tank, and tetrakis(triphenylphosphine)palladium (Pd(PPh ₃ ) ₄ ) (1.12 g, 0.97 mmole) and 30 ml were added. The ethanol was heated and stirred, heated to 80 ° C and allowed to react overnight. After the reaction was completed, 300 ml of deionized water was added, and after stirring for 30 minutes, the stirring was stopped, the mixture was allowed to stand, and the mixture was filtered. The crude product was obtained, and the mixture was purified by chromatography using a Soxhlet extractor, and concentrated to a thick concentration. The solid phase was added to a solution of 300 ml of hexane to enhance precipitation, and the organic layer was combined and filtered to give a white solid compound 1-2 (about 5.5 g).

Compound 1-2 ¹ H NMR: ¹ H NMR (CDCl ₃ , 400 MHz), δ 10-9.92 (S, 1H); 9.02-8.99 (m, 2H); 8.85-8.82 (S, 1H); 8.85-8.7 (d) , 1H); 8.44 - 8.41 (d, 2H); 8.39-8.36 (d, 1H); 8.35-7.47 (m, 18H).

Synthesis Example 3: Synthesis of Compound 1-3

The reactant C (10 g, 19.4 mmole) and dibenzo[b,d]thiophen-4-ylboronic acid (5.31 g, 23.28 mmole) were placed in a reaction tank, and 120 ml of toluene was added. . Potassium carbonate (9.38 g, 67.9 mmole) was dissolved in 70 ml of deionized water and added to the reaction tank, and tetrakis(triphenylphosphine)palladium (Pd(PPh ₃ ) ₄ ) (1.12 g, 0.97 mmole) and 30 ml were added. The ethanol was heated and stirred, heated to 80 ° C and reacted overnight. After the reaction was completed, 300 ml of deionized water was added, and after stirring for 30 minutes, the stirring was stopped and allowed to stand, and the layers were separated. After removing the aqueous layer, it was purified by silica gel chromatography, and concentrated to a thick state to be added with 300 ml of hexane. The organic layer was combined and filtered to give a white solid solid compound 1-3 (~8 g).

Compound 1-3 ¹ H NMR: ¹ H NMR (CDCl ₃ , 400 MHz), δ 9.96-9.94 (S, 1H); 9.01-8.99 (m, 2H): 8.76-8.75 (d, 1H); 8.72-8.71 , 1H); 8.45-8.38 (m, 3H); 8.25-8.23 (m, 4H); 7.95-7.44 (m, 14H).

Synthesis Example 4: Synthesis of Compounds 1-5

Reaction C (10 g, 19.4 mmole) with 4-(1-phenyl-1H-benzimidazol-2-yl)phenylboronic acid (4-(1-phenyl-1H-benzo[d]imidazol-2- Yl)phenyl)boronic acid) (7.31 g, 23.28 mmole) was placed in a reaction tank, and 120 ml of toluene was added. Potassium carbonate (9.38 g, 67.9 mmole) was dissolved in 70 ml of deionized water and added to the reaction tank, and tetrakis(triphenylphosphine)palladium (Pd(PPh ₃ ) ₄ ) (1.12 g, 0.97 mmole) and 30 ml were added. The ethanol was heated and stirred, heated to 80 ° C and reacted overnight. After the reaction was completed, 300 ml of deionized water was added, and after stirring for 30 minutes, the stirring was stopped and allowed to stand for stratification. After removing the aqueous layer, it was purified by silica gel chromatography and concentrated to a thick state to add 300 ml of hexane. The organic layer was combined and filtered to give a pale green solid compound 1-5 (about 7.5 g).

Compound 1-5 ¹ H NMR: ¹ H NMR (CDCl ₃ , 400 MHz), δ 9.94-9.92 (S, 1H); 8.99-8.98 (m, 3H); 8.76-8.76 (m, 1H); 8.45-8.44 (S , 2H); 8.44-8.42 (d, 3H); 8.27-8.25 (t, 3H); 8.19-8.17 (S, 2H); 7.93-7.3 (m, 17H).

Synthesis Example 5: Synthesis of Compounds 1-6

The reactant C (10 g, 19.40 mmole) and 3-(pyridin-3-yl)phenylboronic acid (4.633 g, 23.28 mmole) were placed in a reaction tank. Add 120 ml of toluene. Potassium carbonate (9.384 g, 67.9 mmole) was dissolved in 70 ml of deionized water and added to the reaction tank, and tetrakis(triphenylphosphine)palladium (Pd(PPh ₃ ) ₄ ) (1.12 g, 0.97 mmole) and 30 ml were added. The ethanol was heated and stirred, heated to 80 ° C and reacted overnight. After the reaction was completed, 300 ml of deionized water was added, and after stirring for 30 minutes, the stirring was stopped, the mixture was allowed to stand, and the mixture was filtered. The crude product was obtained, and the mixture was purified by chromatography using a Soxhlet extractor and concentrated to a thick consistency. The precipitate was added to a mixture of 300 ml of hexane, and the organic layer was combined and filtered to give a white solid solid compound 1-6 (about 4.3 g).

Compound 1-6 ¹ H NMR: ¹ H NMR (CDCl ₃ , 400 MHz), δ 9.9-9.8 (S, 1H); 8.99-8.95 (m, 3H); 8.79 - 8.75 (t, 1H); 8.64 - 8.63 (d , 1H); 8.54-8.51 (S, 1H); 8.45-8.43 (d, 3H); 8.26-8.25 (d, 2H); 8.25-8.21 (d, 1H); 8.20-7.99 (S, 1H); -7.40 (m, 13H).

Synthesis Example 6: Synthesis of Compound 1-7

Compound A (10 g, 40.737 mmole) and 3,5-dibromobenzaldehyde (11.74 g, 44.48 mmole) were placed in a reaction tank, and after thoroughly removing water, 230 ml of ethanol was added thereto, and stirring was started. Sodium methoxide (0.655 g, 12.31 mmole) was added and stirred at room temperature for 16 h. Thereafter, 3-Amidinopyridinium chloride (6.7 g, 44.34 mmole) and sodium hydroxide (3.22 g, 80.61 mmole) were added, and 30 ml of toluene was added thereto, and the heating device was turned on and heated until 75 ° C and react overnight. After completion of the reaction, the solid was filtered, and then stirred and stirred with 250 ml of toluene, and the solid was filtered to give a white solid compound D (about 6.3 g).

Compound D (10 g, 16.83 mmole) and 1-naphthylboronic acid (1-Naphthalenylboroni _{toluene/ethanol/water, reflux} , 42.07 mmole) were placed in a reaction vessel, and 120 ml of toluene was added. Potassium carbonate (18.768 g, 135.8 mmole) was dissolved in 70 ml of deionized water and added to the reaction tank, and tetrakis(triphenylphosphine)palladium (Pd(PPh ₃ ) ₄ ) (2.24 g, 1.94 mmole) and 30 ml were added. The ethanol was heated and stirred, heated to 80 ° C and allowed to react overnight. After the reaction was completed, 300 ml of deionized water was added, and after stirring for 30 minutes, the stirring was stopped, the mixture was allowed to stand, and the mixture was filtered. The crude product was obtained, and the mixture was purified by chromatography using a Soxhlet extractor, and concentrated to a thick concentration. The solid phase was added to a solution of 300 ml of hexane to enhance precipitation, and the organic layer was combined and filtered to give a white solid solid compound 1-7 (about 6.5 g). _{^{1 H NMR (CDCl 3, 400MHz}} ), δ 9.916 (d, 1H), 8.95-8.98 (m, 2H), 8.73 (dd, 1H), 8.52 (d, 2H), 8.42 (d, 2H), 8.23- 8.25(m,2H), 8.13(d,2H), 7.98(m,4H),7.88(m,4H),7.81(d,1H), 7.61-7.67(m,5H),7.51-7.56(m, 4H), 7.41-7.50 (m, 2H).

Synthesis Example 7: Synthesis of Compound 1-8

Reaction C (10 g, 19.40 mmole) and quinolin-8-ylboronic acid (4.027 g, 23.28 mmole) were placed in a reaction vessel, and 120 ml of toluene was added. Potassium carbonate (9.384 g, 67.9 mmole) was dissolved in 70 ml of deionized water and added to the reaction tank, and tetrakis(triphenylphosphine)palladium (Pd(PPh ₃ ) ₄ ) (1.12 g, 0.97 mmole) and 30 ml were added. The ethanol was heated and stirred, heated to 80 ° C and reacted overnight. After the reaction was completed, 300 ml of deionized water was added, and after stirring for 30 minutes, the stirring was stopped and allowed to stand for stratification, and the crude product was obtained by filtration, and the mixture was purified by chromatography using a Soxhlet extractor, and concentrated to a thick layer. The precipitate was added to a mixture of 300 ml of hexane, and the organic layer was combined and filtered to give a white solid solid compound 1-8 (about 5.5 g).

Compound 1-8 ¹ H NMR: ¹ H NMR (CDCl ₃ , 400 MHz), δ 9.95-9.9 (S, 1H); 8.99-8.98 (m, 3H); 8.75-8.74 (d, 1H); 8.62. S, 1H); 8.43-8.42 (d, 2H); 8.41-8.37 (d, 1H); 8.27-8.27 (m, 3H); 7.92-7.4 (m, 13H).

Synthesis Example 8: Synthesis of Compound 1-10

The reactant C (10 g, 19.4 mmole) and (10-phenylanthracen-9-yl) boronic acid (6.36 g, 21.32 mmole) were placed in a reaction tank, and 120 was added. ML of toluene. Potassium carbonate (9.38 g, 67.9 mmole) was dissolved in 70 ml of deionized water and added to the reaction tank, and tetrakis(triphenylphosphine)palladium (Pd(PPh ₃ ) ₄ ) (0.67 g, 0.582 mmole) and 30 ml were added. The ethanol was heated and stirred, heated to 80 ° C and reacted overnight. After the reaction was completed, 300 ml of deionized water was added, and after stirring for 30 minutes, the stirring was stopped and allowed to stand, and the layers were separated. After removing the aqueous layer, it was purified by silica gel chromatography, and concentrated to a thick state to be added with 300 ml of hexane. The organic layer was combined and filtered to give a pale yellow solid compound 1-10 (~ 3.2 g).

Compound 1-10 ¹ H NMR: ¹ H NMR (CDCl ₃ , 400 MHz), δ 9.95-9.93 (S, 1H); 8.97-8.96 (m, 2H); 8.74 - 8.72 (m, 1H); 8.58-8.56 ( d, 1H); 8.56-8.54 (m, 3H); 8.45-8.43 (m, 2H); 7.93-7.66 (m, 22H).

Synthesis Example 9: Synthesis of Compound 1-11

Reactant C with (10-[1,1'-biphenyl]-4-yl-9-mercapto)-boronic acid (10-([1,1'-biphenyl]-4-yl)anthracen-9- Yl) Boronic acid (10.89 g, 29.1 mmole) was placed in a reaction tank, and 120 ml of toluene was added. Potassium carbonate (9.38 g, 67.9 mmole) was dissolved in 70 ml of deionized water and added to the reaction tank, and tetrakis(triphenylphosphine)palladium (Pd(PPh ₃ ) ₄ ) (0.56 g, 0.485 mmole) and 30 ml were added. The ethanol was heated and stirred and heated to 80 °C. After the reaction was completed, 300 ml of deionized water was added, and after stirring for 30 minutes, the stirring was stopped and allowed to stand, and the layers were separated. After removing the aqueous layer, it was purified by silica gel chromatography, and concentrated to a thick state to be added with 300 ml of hexane. The organic layer was combined and filtered to give a pale yellow solid compound 1-11 (~ 4.4 g).

Compound 1-11 ¹ H NMR: ¹ H NMR (CDCl ₃ , 400 MHz), δ 9.95-9.92 (S, 1H); 8.95-8.93 (m, 2H); 8.7-8.6 (m, 1H); 8.58-8.56 ( d, 1H); 8.56-8.54 (m, 3H); 8.420-8.402 (m, 2H); 7.094-7.26 (m, 26H).

Synthesis Example 10: Synthesis of Compound 1-15

Reaction C (10 g, 19.4 mmole) and 9,9'-spirobi [fluoren]-2-ylboronic acid (8.386 g, 23.2 mmole) were placed in the reaction. In a tank, add 120 ml of toluene. Potassium carbonate (9.38 g, 67.9 mmole) was dissolved in 70 ml of deionized water and added to the reaction tank, and tetrakis(triphenylphosphine)palladium (Pd(PPh ₃ ) ₄ ) (0.672 g, 0.582 mmole) and 30 ml were added. The ethanol was heated and stirred, heated to 80 ° C and reacted overnight. After the reaction was completed, 300 ml of deionized water was added, and after stirring for 30 minutes, the stirring was stopped and allowed to stand, and the layers were separated. After removing the aqueous layer, it was purified by silica gel chromatography, and concentrated to a thick state to be added with 300 ml of hexane. The organic layer was combined and filtered to give a white solid solid compound 1-15 (~ 7.2 g).

Compound 1-15 ¹ H NMR: ¹ H NMR (CDCl ₃ , 400 MHz), δ 9.8-9.7 (s, 1H); 8.97-8.96 (m, 1H); 8.74 - 8.73 (m, 1H); 8.58-8. d, 1H); 8.4-8.35 (m, 3H); 8.3-8.25 (m, 1H); 8.17-8.15 (m, 1H); 8.8.1-8.07 (s, 1H); 7.94-7.39 (m, 17H); 7.17-7.1 (t, 3H); 7.03-7.01 (s, 1H); 6.81-6.78 (d, 2H), 6.5-6.4 (s, 1H).

Synthesis Example 11: Synthesis of Compound 1-22

3'-Bromoacetophenone (10 g, 50.23 mmole) and quinolin-8-ylboronic acid (9.12 g, 52.75 mmole) were placed in a reaction tank, and 120 ml was added. Toluene. Potassium carbonate (18.05 g, 130.6 mmole) was dissolved in 70 ml of deionized water and added to the reaction tank, and tetrakis(triphenylphosphine)palladium (Pd(PPh ₃ ) ₄ ) (1.74 g, 1.507 mmole) and 30 ml were added. The ethanol was heated and stirred, heated to 80 ° C and reacted overnight. After the reaction was completed, 300 ml of deionized water was added, and after stirring for 30 minutes, the stirring was stopped and allowed to stand for stratification. After removing the aqueous layer, it was purified by silica gel chromatography and concentrated to a thick color to obtain a pale yellow liquid compound E ( About 5.5 grams).

Compound E (10 g, 40.737 mmole) and 3-bromobenzaldehyde (8.23 g, 44.48 mmole) were placed in a reaction tank, and after thoroughly removing water, 230 ml of ethanol was added, stirring was started, and sodium methoxide was added ( 0.655 g, 12.31 mmole), stirred at room temperature for 16 hours. Thereafter, 3-Amidinopyridinium chloride (6.7 g, 44.34 mmole) and sodium hydroxide (3.22 g, 80.61 mmole), and 30 ml of toluene were added, the heating device was turned on, heated to 75 ° C and reacted overnight. After the reaction was completed, the mixture was further stirred with 250 ml of toluene and the solid was filtered to give a white solid compound F (about 4.5 g).

Compound F (10 g, 19.4 mmole) and (10-phenylanthracen-9-yl) boronic acid (6.36 g, 21.32 mmole) were placed in a reaction tank, and 120 ml was added. Toluene. Potassium carbonate (9.38 g, 67.9 mmole) was dissolved in 70 ml of deionized water and added to the reaction tank, and tetrakis(triphenylphosphine)palladium (Pd(PPh ₃ ) ₄ ) (0.67 g, 0.582 mmole) and 30 ml were added. The ethanol was heated and stirred, heated to 80 ° C and reacted overnight. After the reaction was completed, 300 ml of deionized water was added, and after stirring for 30 minutes, the stirring was stopped and allowed to stand, and the layers were separated. After removing the aqueous layer, it was purified by silica gel chromatography, and concentrated to a thick state to be added with 300 ml of hexane. The organic layer was combined and filtered to give a pale-yellow solid compound 1-22 (~3 g).

Synthesis Example 12: Synthesis of Compound 1-23

Compound A (10 g, 40.737 mmole) and 3-bromobenzaldehyde (8.23 g, 44.48 mmole) were placed in a reaction tank, and after thoroughly removing water, 230 ml of ethanol was added, stirring was started, and sodium methoxide was added ( 0.655 g, 12.31 mmole), stirred at room temperature for 16 hours. Thereafter, 2-Amidinopyridinium chloride (6.7 g, 44.34 mmole) and sodium hydroxide (3.22 g, 80.61 mmole) were added, and 30 ml of toluene was added thereto, and the heating device was turned on and heated until 75 ° C and react overnight. After completion of the reaction, the solid was filtered, and the mixture was stirred and stirred with 250 ml of toluene, and the solid was filtered to give a white solid compound G (about 3.8 g).

Compound G (10 g, 19.4 mmole) and (10-phenylanthracen-9-yl) boronic acid (6.36 g, 21.32 mmole) were placed in a reaction tank, and 120 ml was added. Toluene. Potassium carbonate (9.38 g, 67.9 mmole) was dissolved in 70 ml of deionized water and added to the reaction tank, and tetrakis(triphenylphosphine)palladium (Pd(PPh ₃ ) ₄ ) (0.67 g, 0.582 mmole) and 30 ml were added. The ethanol was heated and stirred, heated to 80 ° C and reacted overnight. After the reaction was completed, 300 ml of deionized water was added, and after stirring for 30 minutes, the stirring was stopped and allowed to stand, and the layers were separated. After removing the aqueous layer, it was purified by silica gel chromatography, and concentrated to a thick state to be added with 300 ml of hexane. The organic layer was combined and filtered to give a pale yellow solid compound 1-23 (~ 3.3 g).

The physical property values of the above materials are shown in Table 2. The method of measuring each physical property value is as follows.

(1) Thermal cracking temperature (T _d )

The thermogravimetric analyzer (Perkin Elmer, TGA 8000) was used for measurement, and the pyrolysis property of the obtained compound was measured at a normal temperature and nitrogen atmosphere at a programmed temperature of 20 ° C / min. The temperature at which the weight is reduced to 95% of the initial weight is the thermal cracking temperature (T _d ).

(2) Glass transition temperature (T _g )

The prepared compound was measured using a differential scanning calorimeter (DSC; Perkin Elmer, DSC 8000) at a programmed temperature rate of 20 ° C/min.

(3) The energy level of the highest occupied molecular orbital (HOMO)

In addition, the compound was made into a thin film state, and its ionization potential value was measured under a atmosphere using a photoelectron spectrophotometer (Riken Keiki, Surface Analyzer), and the value was further converted to a HOMO energy level value.

(4) The lowest unoccupied molecular orbital (LUMO) energy level value

The film of the above compound was measured by a UV/VIS spectrophotometer (Perkin Elmer, Lambda 20) for the onset of the absorption wavelength, and the value was converted into an energy gap value to enable the energy gap value and the HOMO energy level. The value is subtracted, That is, the LUMO energy level is obtained.

(5) Triplet energy value (E _T )

The luminescence spectrum was measured using a fluorescence spectrometer (Perkin Elmer, LS 55) at a temperature of 77 K, and then E _T was obtained by calculation.

Example 1: Fabrication of Organic Electroluminescent Devices

Before the substrate is loaded into the vapor deposition system, the substrate is first degreased with solvent and ultraviolet ozone. Thereafter, the substrate is transferred to a vacuum deposition chamber, and all layers are deposited on top of the substrate. The layers shown in Figure 2 are sequentially deposited by a heated vapor boat at a vacuum of about 10 ^-6 Torr: a) a hole injection layer, 20 nm thick, containing 9% p. Type electrically conductive dopant HTM, wherein the p-type electrically conductive dopant is purchased from Shanghai Yufeng Chemical Co., Ltd., and the HTM is purchased from Merck & Co., Inc.; b) hole transport layer, Thickness 170 nm, HTM; c) exciton blocking layer, thickness 10 nm, HT (manufactured by 昱 radium photoelectric); d) luminescent layer, thickness 25 nm, containing EBH doped with 4% by volume BD, wherein , BD and EBH are prepared by 昱 radium photoelectric; e) electron transport layer, thickness 25 nm, containing compound 1-1 and doped quinoline lithium (Liq, 昱 radium photoelectric preparation), volume ratio is 1:1; f An electron injecting layer having a thickness of 0.5 nm, lithium fluoride (LiF), and g) a cathode having a thickness of about 180 nm and containing A1.

The structure of the element can be expressed as: ITO/HTM: p-type electrically conductive dopant (20 nm) / HTM (170 nm) / HT (10 nm) / EBH: BD (25 nm) / compound 1-1 : Liq (25 nm) / LiF (0.5 nm) / Al (180 nm).

After deposition to form the above layers, the component is transferred from the deposition chamber to a dry box and then encapsulated with a UV curable epoxy resin and a glass cover containing a moisture absorbent. The organic electroluminescent device has a light-emitting area of 9 square millimeters.

Examples 2 to 7: Fabrication of organic electroluminescent elements

Except that the compound 1-1 of the electron transport layer in Example 1 was replaced with the compounds 1-2, 1-3, 1-5, 1-10, 1-11 and 1-15, respectively, Example 2, Example 3 Example 4, Example 5, Example 6 and Example 7 are layer structures as in Example 1.

Comparative Example 1: Fabrication of organic electroluminescent elements

The organic electroluminescent device was placed in a layer structure similar to that of Example 1, except that the compound 1-1 of the electron transporting layer in Example 1 was replaced with the compound EET09, and the organic electroluminescent device structure could be represented by, for example, ITO/HTM. : p dopant (20 nm) / HTM (170 nm) / HT (10 nm) / EBH: BD (25 nm) / compound EET09: Liq (25 nm) / LiF (0.5 nm) / Al (180 nm).

Among them, the compound EET09 is as described in Japanese Patent No. 2011003793A.

The electroluminescent properties of the above-mentioned organic electroluminescent device are all based on a constant current source (KEITHLEY 2400 Source Meter, made by Keithley Instruments, Inc., Cleveland, Ohio) and a photometer (PHOTO RESEARCH SpectraScan PR 650, made by Photo) Research, Inc., Chatsworth, Calif.) measured its luminescent properties at room temperature, based on the organic electroluminescent device of the comparative example (standard value is 1), and its driving voltage, luminous efficiency and value of LT95 are listed. Shown in Table 3. Among them, the LT95 value is defined as the time taken for the brightness level to fall to a level of 95% relative to the initial brightness as a measure of the service life or stability of the organic electroluminescent element.

As described above, it is seen that the organic electroluminescent device comprising the quinoline-substituted diphenylpyrimidine compound having the structure of the formula (I) of the present invention exhibits good heat resistance within a range of acceptable driving voltage and luminous efficiency loss. The service life of the organic electroluminescent device of the present invention is suitable for applications such as vehicle displays, and has extremely high technical value.

The above embodiments are merely illustrative and are not intended to limit the invention. Modifications and variations of the above-described embodiments can be made by those skilled in the art without departing from the spirit and scope of the invention. Therefore, the right of the present invention The scope of protection is defined by the scope of the patent application attached to the present invention, and should be included in the technical scope of the disclosure as long as it does not affect the effects and the purpose of the present invention.

Claims (13)

A quinoline substituted diphenylpyrimidine compound having the structure of formula (I): Wherein X ₁ represents a substituted or unsubstituted C _6-30 aryl group, substituted or unsubstituted C _5-30 containing at least one hetero atom selected from the group consisting of N, O, and S; a heteroaryl group; A ₁ represents a substituted or unsubstituted C _6-36 aryl group, substituted or unsubstituted C ₅ containing at least one hetero atom selected from the group consisting of N, O, and S; _{-30heteroaryl} ; X ₁ and A ₁ are the same or different, and at least one of them is substituted or unsubstituted, and contains at least one hetero atom selected from the group consisting of N, O, and S. _{5-30heteroaryl} ; and n represents an integer of 1 or 2, and when n represents 2, each of A ₁ is the same or different. The quinoline-substituted diphenylpyrimidine compound having the structure of the formula (I) as described in claim 1 is represented by the structure of the formula (I-1) or the structure of the formula (I-2): Wherein X ₁ represents a substituted or unsubstituted C _6-30 aryl group, substituted or unsubstituted C _5-30 containing at least one hetero atom selected from the group consisting of N, O, and S; a heteroaryl group; A ₁ represents a substituted or unsubstituted C _6-36 aryl group, substituted or unsubstituted C ₅ containing at least one hetero atom selected from the group consisting of N, O, and S; _{-30heteroaryl} ; X ₁ and A ₁ are the same or different, and at least one of them is substituted or unsubstituted, and contains at least one hetero atom selected from the group consisting of N, O, and S. _{5-30heteroaryl} ; and n represents an integer of 1 or 2, and when n represents 2, each of A ₁ is the same or different. A quinoline-substituted diphenylpyrimidine compound having the structure of the formula (I) according to the first aspect of the invention, wherein X ₁ is a pyridyl group, a quinolyl group or a naphthyl group. A quinoline-substituted diphenylpyrimidine compound having the structure of formula (I) as described in claim 2, wherein X ₁ is selected from one of the group consisting of: Wherein Xr represents hydrogen, fluorine, cyano, C _1-4 alkyl or unsubstituted C _6-18 aryl. A quinoline-substituted diphenylpyrimidine compound having the structure of the formula (I) according to the first aspect of the invention, wherein the A ₁ is selected from one of the group consisting of: Wherein L represents O or S; and Ar ₁ to Ar ₆ each independently represent hydrogen, an unsubstituted C _6-18 aryl group; and R ₁ to R ₄ each independently represent hydrogen, substituted or unsubstituted C _6-12 The aryl group, R ₁ and R ₂ together with the attached carbon atom form a C _6-18 fused aromatic ring system or R ₃ and R ₄ together with the attached carbon atom form a C _6-18 fused aromatic ring system; One of Y ₁ and Y ₂ is a single bond and is attached to the compound of formula (I), the other being hydrogen. A quinoline-substituted diphenylpyrimidine compound having the structure of the formula (I) according to claim 5, wherein the unsubstituted C _6-18 aryl group is a phenyl group, and the unsubstituted The C _6-12 aryl group is a phenyl group. A quinoline-substituted diphenylpyrimidine compound having the structure of the formula (I) according to claim 1, wherein when n is 1, the compound of the formula (I) is a formula (I-3) or Formula (I-4): The quinoline-substituted diphenylpyrimidine compound having the structure of the formula (I) as described in claim 1 is one of the compound (1-10) or the compound (1-11): A quinoline-substituted diphenylpyrimidine compound having the structure of the formula (I) according to the first aspect of the invention, wherein when n is 2, the compound of the formula (I) is a formula (I-5) Show: A quinoline-substituted diphenylpyrimidine compound having the structure of the formula (I) as described in claim 8 wherein A ₁ is the same structure. An organic electroluminescent device comprising: a cathode; an anode; and an organic layer interposed between the cathode and the anode, and the organic layer comprises the structure of the formula (I) as described in claim 1 Quinoline substituted diphenylpyrimidine compound. The organic electroluminescent device of claim 11, wherein the organic layer is an electron transport layer and has a thickness of from 20 nm to 30 nm. The organic electroluminescent device according to claim 12, wherein the electron transporting layer further comprises an N-type electrically conductive dopant, and the content of the N-type electrically conductive dopant is 5% by weight to 50% by weight. %.