CN101220034A - A kind of Λ-type hypergas base derivative organic electroluminescent material - Google Patents

Abstract

The invention relates to a high-brightness, high-efficiency Λ-type Trger's base (abbreviated as TB) derivative organic electroluminescent material, which belongs to the technical field of organic electroluminescent materials. A Λ-type hypergoss base derivative organic electroluminescent compound, which is characterized in that it has a Λ-type super Goss base skeleton, and the general structure is as above, wherein Ar is a substituted or unsubstituted large π-conjugated aryl or heteroaryl. The Λ-type superges base (TB) derivative organic compound not only has a large conjugated system, but also can effectively eliminate the problem of fluorescence quenching in the solid state, and the synthesis method is simple, which is suitable for the field of organic optoelectronics, especially A new class of organic electroluminescent materials.

Description

A kind of Λ-type hypergas base derivative organic electroluminescent material

technical field

The invention relates to a high-brightness, high-efficiency Λ-type Tröger's base (abbreviated as TB) derivative organic electroluminescent material, which belongs to the technical field of organic electroluminescent materials.

Background technique

Organic light-emitting diodes (OLED) is a new concept display technology with great development prospects, and it is also the most enthusiastic research object in the field of display technology. OLED has a series of advantages such as self-illumination, low-voltage DC drive, full curing, wide viewing angle, and rich colors. Compared with LCD (Liquid Crystal Display, referred to as LCD), OLED has the advantages of no need for backlight, large viewing angle, low power, fast response, low cost, etc.; Compared with Plasma Display Panel (PDP for short), OLED is quite adaptable, ranging from color screens of mobile phones, PDAs, and digital cameras to large computer monitors, digital TVs, and even other large-screen display occasions, OLED can show its skills . What's more attractive is that OLED displays can be made into ultra-thin, translucent or even curly shapes, which can completely bring about a revolution in applications, and are considered to be the third-generation display technology after LCD. Therefore, organic electroluminescent displays have very broad application prospects.

At present, OLED has initially entered the stage of commercialization and is mainly used in small-screen applications such as handheld computers, mobile phones, and digital cameras, but there are still defects in service life, and the preparation process and equipment of the device are not perfect; It is not yet mature enough, and further improvement of materials and devices is urgently needed.

The basic research on organic EL is currently mainly focused on improving the efficiency and life of the device and finding new and improved materials. Luminescent material is the core part in OLED. Studies have shown that organic compounds with larger conjugations generally have stronger fluorescence, however, such compounds are greatly quenched in solid state due to strong π-π interactions; especially for one-dimensional chains or Two-dimensional planar conjugated organic molecules can easily form face-to-face H-aggregations in the solid state, which increases the non-radiative dissipation of excited state energy, thereby significantly weakening its fluorescence in the solid state. However, in organic electroluminescent devices, luminescent materials are used in the form of thin films, so finding organic substances that are not easy to quench fluorescence in solid state has become an important way to improve the performance of organic electroluminescent devices.

Supergers base (TB) derivatives have a rigid, chiral Λ-type cavity structure, and the introduction of this Λ-type steric hindrance skeleton bridge in the light-emitting system can significantly reduce the fluorescence quenching phenomenon of the aggregated state of the material . At the same time, the synthesis method of TB derivatives is simple, and the chemical modification is strong. By selecting precursors of different systems, various large conjugated groups such as fluorene, anthracene, carbazole, naphthalene, triphenylamine and other chromophores can be synthesized. By introducing its flanks, a series of new high-performance luminescent materials can be obtained.

Contents of the invention

Aiming at the deficiencies of the prior art, the invention provides a novel fluorescent material, which can be used as a luminescent material in organic electroluminescent devices, and expands the types of organic luminescent materials used in organic electroluminescent devices.

A kind of Λ-type structure supergess base (TB) derivative organic compound, general structural formula is as follows:

Ar is a substituted or unsubstituted large π-conjugated aryl or heteroaryl group.

Preferably, the Λ-type Super Gess base (TB) derivative organic electroluminescent compound, the compound structural formula is as follows:

Among them, R ₁ is an alkyl group with 1 to 24 carbon atoms, an unsubstituted or alkyl-substituted aromatic group; R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , and R ₇ are independently a hydrogen atom, benzene, bis Benzene, naphthalene, anthracene, phenanthrene, pyrene, fluorene, bifluorene, spirofluorene, carbazole, indolecarbazole, triarylamine, pyridine, thiophene, bithiophene, dithiophene, furan, imidazole, phenothiazine, iminostilbene one of the groups.

Preferably, the Λ-type Super Gess base (TB) derivative organic electroluminescent compound, the compound structural formula is as follows:

Wherein, R ₂ and R ₄ are independently hydrogen atom, benzene, biphenyl, naphthalene, anthracene, phenanthrene, pyrene, fluorene, bifluorene, spirofluorene, carbazole, indolecarbazole, triarylamine, pyridine, thiophene, biphenyl One of thiophene, thiophene, furan, imidazole, phenothiazine, and iminostilbene groups.

Preferably, the Λ-type Super Gess base (TB) derivative organic electroluminescent compound, the compound structural formula is as follows:

Among them, R ₁ is an alkyl group with 1 to 24 carbon atoms, an unsubstituted or alkyl-substituted aryl group; R ₃ , R ₄ , R ₅ , R ₆ , and R ₈ are independently hydrogen atoms, benzene, biphenyl, naphthalene , anthracene, phenanthrene, pyrene, fluorene, bifluorene, spirofluorene, carbazole, indolecarbazole, triarylamine, pyridine, thiophene, bithiophene, and thiophene, furan, imidazole, phenothiazine, iminostilbene group kind of.

Preferably, the Λ-type Super Gess base (TB) derivative organic electroluminescent compound, the compound structural formula is as follows:

Wherein, X is one of O, S, and Se atoms, R ₂ , R ₃ , and R ₄ are independently hydrogen atoms, benzene, biphenyl, naphthalene, anthracene, phenanthrene, pyrene, fluorene, bifluorene, spirofluorene, carba One of azole, indolecarbazole, triarylamine, pyridine, thiophene, bithiophene, thiophene, furan, imidazole, phenothiazine, and iminostilbene groups.

More preferably, in the Λ-type supergas base (TB) derivative organic electroluminescent compound, R ₁ is selected from one of the groups A1 to A13 in Table 1, and R ₂ , R ₄ and R ₇ are selected from the group in Table 1. One of the groups A12 to A34 in 1.

Table 1

The application of the Λ-type hypergas base derivative organic electroluminescent compound in the light-emitting layer of the organic electroluminescent device composed of multi-layer organic materials.

Detailed description of the invention

According to nine kinds of structures of above-mentioned I～IX, in conjunction with table 1, the present invention is further elaborated:

For class I compounds, the preferred substituent R ₁ can be one of the groups A1-A13 in Table 1, and R ₂ can be one of the groups A12-A34. Particularly preferred compounds in Class I structure are I-1 to I-18, the structural formula is as follows:

Class II compounds, the preferred substituent _R can be one of the groups A12 to A34 listed in Table 1, and the particularly preferred compounds in the Class II structure are II-1 to II-16, and the structural formula is as follows:

Class III compounds, preferred substituents R ₂ , R ₄ , and R ₇ may be one of the same or different groups A12 to A34 in Table 1, and particularly preferred compounds in Class III structures are III-1 to III-16, the structural formula is as follows:

Class IV compounds, preferred substituents R ₂ and R ₄ may be one of the same or different groups A12 to A34 in Table 1, and particularly preferred compounds in Class IV structures are IV-1 to IV-18 , the structural formula is as follows:

Class V compound, structural formula is as follows:

Class VI compounds, the structural formula is as follows:

Class VII compounds, the preferred substituent R ₁ is one of the groups A1-A13 in Table 1, R ₂ can be one of A12-A34, and the particularly preferred compounds in the class VII structure are VII-1 to VII-16, the structural formula is as follows:

Class VIII compounds, the preferred substituent R ₁ is one of the groups A1 to A13 in Table 1, R ₄ can be one of A12 to A34, and the particularly preferred compounds in the VIII class structure are VIII-1 to VIII-17, the structural formula is as follows:

Class IX compounds, the preferred substituent X can be O, S, one of Se atoms, _R4 can be one of the groups A12～A34 in Table 1, and the particularly preferred compound in the class IX structure is IX -1-1 to IX-3-16, the structural formula is as follows:

The present invention has the following advantages:

The Λ-type superges base (TB) derivative organic compound not only has a large conjugated system, but also can effectively eliminate the problem of fluorescence quenching in the solid state, and the synthesis method is simple, which is suitable for the field of organic optoelectronics, especially A new class of organic electroluminescent materials.

Supergers base (TB) derivatives have a rigid, chiral Λ-type cavity structure, and the introduction of this Λ-type steric hindrance skeleton bridge in the light-emitting system can significantly reduce the fluorescence quenching phenomenon of the aggregated state of the material . At the same time, the synthesis method of superges base (TB) derivatives is simple, and the chemical modification is strong. By selecting different system precursors, various large conjugated groups such as fluorene, anthracene, carbazole, naphthalene, Chromophores such as triphenylamine are introduced into its flanks, so that a series of new high-performance luminescent materials can be obtained.

Description of drawings:

Fig. 1 is the electroluminescent spectrum of the electroluminescent device of the representative compound TBF-BP of the Λ-type Supergus base (TB) derivative light-emitting material of the present invention;

Fig. 2 is the voltage-current density-brightness spectrogram of the electroluminescent device of the representative compound TBF-BP of Λ-type supergus base (TB) derivative luminescent material of the present invention;

Fig. 3 is the electroluminescent spectrum of the electroluminescent device of the representative compound TBA of Λ-type superguss base (TB) derivative luminescent material of the present invention;

Fig. 4 is the voltage-current density-brightness spectrogram of the electroluminescence device of the representative compound TBA of the Λ-type supergas base (TB) derivative light-emitting material of the present invention.

Detailed ways:

The present invention will be further elaborated below in conjunction with the embodiments and the accompanying drawings.

Example 1

Synthesis of compound TBF:

In a 50 ml three-neck flask, 2.94 g of 9,9-dibutyl-2-aminofluorene and 1.4 g of urotropine were added, and 20 ml of trifluoroacetic acid was added under argon protection, and stirred at room temperature for 24 hours. The solvent trifluoroacetic acid was distilled off under reduced pressure, diluted with 10 ml of water, and then neutralized by adding ammonia to a pH value of 8-9. It was extracted three times with dichloromethane, washed twice with water, dried over anhydrous magnesium sulfate, evaporated to remove the solvent, and then purified by column chromatography to obtain 2.08 g of white solid. (67% yield) mp.191°C; ¹ H NMR (CDCl ₃ , 400MHz) δ0.55-0.60 (m, 2H), 0.62-0.73 (m, 18H), 1.03-1.12 (m, 8H), 1.86 -1.90(m, 4H), 1.95(t, J=8.33Hz, 4H), 4.32(d, J=16.56Hz, 2H), 4.44(s, 2H), 4.87(d, J=16.49Hz, 2H) , 7.15(s, 2H), 7.21-7.30(m, 8H), 7.54-7.56(t, 2H). ¹³ C NMR(CDCl ₃ , 400MHz): δ13.33(d, J=35.6HZ), 22.58( d, J=48HZ), 25.54(d, J=49.2HZ), 39.64(d, J=34HZ), 54.2, 58.7, 66.3, 117.0, 118.7, 119.3, 122.4, 125.8, 126.1, 126.2, 136.8, 140.1, 147.1, 149.8, 150.2. MS (ESI+) m/z, 623.8 [M ⁺ ]. Anal. Calcd for C ₄₅ H ₅₄ N ₂ : C, 86.77; H, 8.74; N, 4.50. 8.926; N, 4.378.

Synthesis of compound TBF-Br:

In a 50 ml three-necked flask, add 3.72 g of 9,9-dibutyl-2-amino-7 bromofluorene, 1.4 g of urotropine, add 20 ml of trifluoroacetic acid under argon protection, and stir at room temperature for 24 Hour. The solvent trifluoroacetic acid was distilled off under reduced pressure, diluted with 10 ml of water, and then neutralized by adding ammonia to a pH value of 8-9. It was extracted three times with dichloromethane, washed twice with water, dried over anhydrous magnesium sulfate, evaporated to remove the solvent, and then purified by column chromatography to obtain 2.69 g of a white solid. (69% yield) mp.287°C; ¹ H NMR (CDCl ₃ , 400MHz) δ0.56-0.66 (m, 12H), 0.68-0.72 (m, 8H), 1.02-1.13 (m, 8H), 1.83 -1.87(m, 4H), 1.89-1.96(m, 4H), 4.29(d, J=16.58Hz, 2H), 4.42(s, 2H), 4.85(d, J=16.52Hz, 2H), 7.12( s, 2H), 7.20 (s, 2H), 7.36-7.40 (q, 6H). ¹³ C NMR (CDCl ₃ , 400MHz): δ13.30 (d, J=36HZ), 22.51 (d, J=46HZ) , 25.49(d, J=50.8HZ), 39.53(d, J=29.2HZ), 54.6, 58.7, 66.3, 117.2, 119.3, 120.0, 120.1, 125.8, 126.1, 129.4, 135.8, 139.1, 147.5, 149.5, 152.5 .MS (MALDI-TOF) m/z, 778.2. Anal. Calcd for C ₄₅ H ₅₂ N ₂ Br ₂ : C, 69.23; H, 6.71; N, 3.59. Found: C, 69.21; H, 6.725; N, 3.452.

Synthesis of compound TBF-MP:

Add compound TBF-Br (1.56g, 2mmol) and p-tolueneboronic acid (1.09g, 8mmol) into a 50mL three-necked flask, then add 20mL of dry tetrahydrofuran and stir until dissolved. Under the protection of argon, 10 ml of 2 mol/L NaCO ₃ aqueous solution was added, tetrakis(triphenylphosphine)palladium (0.23 g, 0.2 mmol) was added rapidly, and the temperature was raised to 90° C. under reflux and stirred for 36 hours. After the product system was lowered to room temperature, it was diluted with 30 ml of water, extracted three times with dichloromethane, washed twice with water, dried over anhydrous magnesium sulfate, evaporated to remove the solvent and purified by column chromatography to obtain 1.29 g of a white solid. (81% yield) mp.235°C; ¹ HNMR (CDCl ₃ , 400MHz) δ0.64-0.77 (m, 20H), 1.04-1.13 (m, 8H), 1.92 (t, J=8.16Hz, 4H) , 1.99(t, J=8.27Hz, 4H), 4.33(d, J=16.56Hz, 2H), 4.46(s, 2H), 4.89(d, J=16.32Hz, 2H), 7.17(s, 2H) , 7.24(s, 2H), 7.26(s, 4H), 7.48-7.54(m, 8H), 7.59(d, J=8.45Hz, 2H). ¹³ C NMR (CDCl ₃ , 400MHz): δ13.32( d, J=30.4HZ), 20.6, 22.58(d, J=48.8HZ), 25.60(d, J=49.2HZ), 39.68(d, J=33.2HZ), 54.4, 58.7, 66.3, 117.1, 118.9, 119.3, 120.9, 125.3, 125.8, 126.5, 129.0, 136.4, 136.8, 138.3, 139.0, 139.1, 150.2, 150.9. MS (MALDI-TOF) m/z, 802.7. Anal. Calcd for C ₅₉ H ₆₆ N ₂ : C , 88.23; H, 8.28; N, 3.49.Found: C, 88.76; H, 8.223; N, 3.355.

Synthesis of compound TBF-BP:

Add compound TBF-Br (1.56g, 2mmol) and p-phenylphenylboronic acid (1.58g, 8mmol) into a 50mL three-necked flask, then add 15mL dry tetrahydrofuran and 5ml dry toluene and stir until dissolved. Under the protection of argon, 10 ml of 2 mol/L NaCO ₃ aqueous solution was added, tetrakis(triphenylphosphine)palladium (0.23 g, 0.2 mmol) was added rapidly, and the temperature was raised to 90° C. under reflux and stirred for 36 hours. After the product system was lowered to room temperature, it was diluted with 30 ml of water, extracted three times with dichloromethane, washed twice with water, dried over anhydrous magnesium sulfate, evaporated to remove the solvent and purified by column chromatography to obtain 1.53 g of a white solid. (83% yield) mp.272°C; ¹ H NMR (CDCl ₃ , 400MHz) δ0.66-0.79(m, 20H), 1.06-1.15(m, 8H), 1.95(t, J=8.15Hz, 4H ), 2.02(t, J=8.25Hz, 4H), 4.35(d, J=16.60Hz, 2H), 4.47(s, 2H), 4.91(d, J=16.40Hz, 2H), 7.29(s, 2H ), 7.36(t, J=7.34Hz, 2H), 7.46(t, J=7.62Hz, 4H), 7.56-7.58(t, 4H), 7.62-7.67(m, 8H), 7.71(t, J= 8.57Hz, 8H). ¹³ C NMR (CDCl ₃ , 400MHz): δ13.83(d, J=29.2HZ), 23.08(d, J=47.6HZ), 26.11(d, J=50.8HZ), 40.17( d，J＝30HZ)，54.91，59.23，66.80，117.68，119.51，119.83，121.46，125.87，126.46，127.04，127.32，127.46，127.50，128.83，139.12，139.95，140.54，140.77，150.69，151.50.MS(MALDI -TOF) m/z, 926.8. Anal. Calcd for C ₆₉ H ₇₀ N ₂ : C, 89.37; H, 7.61; N, 3.02.Found: C, 89.28; H, 7.292; N, 2.808.

Synthesis of compound TBF-DBF:

Add compound TBF-Br (1.56g, 2mmol) and 9,9-dibutyl-2-boronic acid fluorene (2.58g, 8mmol) into a 50mL three-necked flask, then add 15mL dry tetrahydrofuran and 5ml dry toluene and stir until dissolved. Under the protection of argon, 10 ml of 2 mol/L NaCO ₃ aqueous solution was added, tetrakis(triphenylphosphine)palladium (0.23 g, 0.2 mmol) was added rapidly, and the temperature was raised to 90° C. under reflux and stirred for 36 hours. After the product system was lowered to room temperature, it was diluted with 30 ml of water, extracted three times with dichloromethane, washed twice with water, dried over anhydrous magnesium sulfate, evaporated to remove the solvent and purified by column chromatography to obtain 2.00 g of a white solid. (85% yield) mp.181°C; ¹ H NMR (CDCl ₃ , 400MHz) δ0.67-0.88 (m, 40H), 1.05-1.18 (m, 16H), 1.95-2.06 (m, 16H), 4.36 (d, J=16.59Hz, 2H), 4.47(s, 2H), 4.92(d, J=16.52Hz, 2H), 7.20(s, 2H), 7.29-7.37(m, 8H), 7.59-7.66( m, 10H), 7.72-7.77 (q, 4H). MS (MALDI-TOF) m/z, 1175.1. _{Anal. Calcd for C87H102N2 : C} , 88.87; H, 8.74; N, 2.38.Found : C, 88.21; H, 8.894; N, 2.265.

Synthesis of compound TBF-TPA:

Add compound TBF-Br (1.56g, 2mmol) and 1-triphenylamine borate (2.31g, 8mmol) into a 50mL three-necked flask, then add 15mL dry tetrahydrofuran and 5ml dry toluene and stir until dissolved. Under the protection of argon, 10 ml of 2 mol/L NaCO ₃ aqueous solution was added, tetrakis(triphenylphosphine)palladium (0.23 g, 0.2 mmol) was added rapidly, and the temperature was raised to 90° C. under reflux and stirred for 36 hours. After the product system was lowered to room temperature, it was diluted with 30 ml of water, extracted three times with dichloromethane, washed twice with water, dried over anhydrous magnesium sulfate, evaporated to remove the solvent and purified by column chromatography to obtain 1.73 g of a white solid. (Yield 78%) mp.174°C; MS (MALDI-TOF) m/z, 1175.1. Anal. Calcd for C ₈₁ H ₈₀ N ₄ : C, 87.68; H, 7.27; N, 5.05.Found: C, 87.67; H, 7.296; N, 4.957.

Synthesis of compound TBA:

In a 50 ml three-neck flask, add diaminoanthracene (0.97 g, 5 mmol) and 6 ml of 95% ethanol, place in an ice-water bath at 0° C., and add 2.5 ml of 35%-40% formalin solution under the protection of argon, Then slowly add 2.2ml of concentrated hydrochloric acid dropwise with a syringe, and after the dropwise addition, slowly raise the temperature to 60°C and stir for 24 hours. After the reaction product system was cooled to room temperature, 40 ml was added to dilute it, and neutralized with ammonia water until the pH value was 8-9. It was extracted four times with dichloromethane, washed twice with water, dried over anhydrous magnesium sulfate, evaporated to remove the solvent, and purified by column chromatography to obtain 0.63 g of a yellow solid. (60% yield) mp.318°C; ¹ H NMR (CDCl ₃ , 400MHz) δ4.62(s, 2H), 4.91(d, J=16.68Hz, 2H), 5.14(d, J=16.66Hz, 2H), 7.37-7.45(m, 6H), 7.81(d, J=9.05Hz, 2H), 7.91(d, J=8.20Hz, 2H), 7.97(d, J=8.32Hz, 2H), 8.19( s, 2H), 8.27(s, 2H). ¹³ C NMR (CDCl ₃ , 400MHz): δ54.58, 66.62, 118.72, 119.66, 124.42, 124.54, 125.24, 126.61, 127.51, 127.54, 127.86, 129.23, 129.42, 130.36, 131.49, 144.07. MS (HPLC) m/z, 423 [M ^- ]. Anal. Calcd for C ₃₁ H ₂₂ N ₂ : C, 88.12; H, 5.25; N, 6.63. , 5.080; N, 6.624.

Example 2

Adopt the obtained compound TBF-BP of the present invention to be used for organic electroluminescence device and describe in detail as follows:

(1) Place the ITO glass after cleaning with cleaning agent and organic solvent and pretreatment with ultraviolet ozone on the sample stage of the vacuum evaporation device, and vacuumize to 5*10 ^-5 Pa.

(2) Evaporate the hole transport layer NPB 30nm.

(3) Evaporation of luminescent layer TBF-BP 40nm.

(4) Evaporate electron transport layer TPBi 40nm.

(5) Lithium fluoride 1nm was vapor-deposited on the electron injection layer.

(6) Evaporate cathode aluminum 80nm.

Add the positive electrode of direct current to the ITO layer, and add the negative electrode to the LiF/Al layer, that is, emit bright blue light from the ITO layer, with luminous peaks at 441nm and 475nm, CIE coordinates (0.163, 0.136), start-up voltage 4.6V, When the voltage is 18.7V, the maximum brightness is 22487cd/m ² , the maximum current efficiency is 2.91cd/A, and the maximum lumen efficiency is 2.44lm/W. The results of the electroluminescent device show that the luminescent material of the present invention has excellent electroluminescence performance.

Example 3

Adopt the obtained compound TBA of the present invention to be used for organic electroluminescence device and describe in detail as follows:

(1) Place the ITO glass after cleaning with cleaning agent and organic solvent and pretreatment with ultraviolet ozone on the sample stage of the vacuum evaporation device, and vacuumize to 5*10 ^-5 Pa.

(2) Evaporate the hole transport layer NPB 30nm.

(3) Evaporate the luminescent layer TBA 40nm.

(4) Evaporate electron transport layer TPBi 40nm.

(5) Lithium fluoride 1nm was vapor-deposited on the electron injection layer.

(6) Evaporate cathode aluminum 80nm.

Add the positive electrode of direct current to the ITO layer, and add the negative electrode to the LiF/Al layer, that is, emit bright and uniform yellow-green light from the ITO layer, with luminous peaks at 522nm and 589nm, CIE coordinates are (0.394, 0.513), and the starting voltage is 3.63V , when the voltage is 19.7V, the maximum brightness is 27685cd/m ² , the maximum current efficiency is 2.20cd/A, and the maximum lumen efficiency is 2.00lm/W. The results of the electroluminescent device show that the luminescent material of the present invention has excellent electroluminescence performance.

As can be seen from the accompanying drawings 1-4, the organic electroluminescent device made with the Λ-type supergas base (TB) derivative compound obtained in the present invention has the advantages of low start-up voltage and high brightness. The performance is much higher than that of one-dimensional chain or two-dimensional planar conjugated molecules with similar composition.

Example 4

A kind of Λ-type hypergoss base derivative organic electroluminescence compound, structural formula is as follows:

Example 5

A kind of Λ-type hypergoss base derivative organic electroluminescence compound, structural formula is as follows:

Example 6

A kind of Λ-type hypergoss base derivative organic electroluminescence compound, structural formula is as follows:

Example 7

A kind of Λ-type hypergoss base derivative organic electroluminescence compound, structural formula is as follows:

Example 8

A kind of Λ-type hypergoss base derivative organic electroluminescence compound, structural formula is as follows:

Example 9

A kind of Λ-type hypergoss base derivative organic electroluminescence compound, structural formula is as follows:

Example 10

A kind of Λ-type hypergoss base derivative organic electroluminescence compound, structural formula is as follows:

Example 11

A kind of Λ-type hypergoss base derivative organic electroluminescence compound, structural formula is as follows:

Example 12

A kind of Λ-type hypergoss base derivative organic electroluminescence compound, structural formula is as follows:

Example 13

A kind of Λ-type hypergoss base derivative organic electroluminescence compound, structural formula is as follows:

Although the present invention has been described in conjunction with preferred embodiments, the present invention is not limited to the foregoing embodiments, it should be understood that the appended claims have outlined the scope of the present invention, and under the guidance of the inventive concept, those skilled in the art should It is appreciated that certain changes made to the various embodiments of the present invention will be covered by the spirit and scope of the claims of the present invention.

Claims (8)

1. an inverse V type ultra-gees alkali derivant organic electroluminescent compounds is characterized in that having this alkali skeleton of Λ-type superlattice, and general structure is as follows:

Wherein, Ar is for replacing or unsubstituted big pi-conjugated aromatic base or assorted aromatic base.

2. inverse V type ultra-gees alkali derivant organic electroluminescent compounds according to claim 1 is characterized in that, this structural formula of compound is as follows:

Wherein, R ₁Be 1～24 carbon atom alkyl, do not replace or aromatic base that alkyl replaces; R ₂, R ₃, R ₄, R ₅, R ₆, R ₇Independently be a kind of in hydrogen atom, benzene, biphenyl, naphthalene, anthracene, phenanthrene, pyrene, fluorenes, difluorene, spiral shell fluorenes, carbazole, indole carbazole, three arylamine, pyridine, thiophene, bithiophene, thiophthene, furans, imidazoles, thiodiphenylamine, the iminostilbene group.

3. inverse V type ultra-gees alkali derivant organic electroluminescent compounds according to claim 1 is characterized in that, this structural formula of compound is as follows:

Wherein, R ₂, R ₄Independently be a kind of in hydrogen atom, benzene, biphenyl, naphthalene, anthracene, phenanthrene, pyrene, fluorenes, difluorene, spiral shell fluorenes, carbazole, indole carbazole, three arylamine, pyridine, thiophene, bithiophene, thiophthene, furans, imidazoles, thiodiphenylamine, the iminostilbene group.

4. inverse V type ultra-gees alkali derivant organic electroluminescent compounds according to claim 1 is characterized in that, this structural formula of compound is as follows:

Wherein, R ₁Be 1～24 carbon atom alkyl, do not replace or aryl that alkyl replaces; R ₃, R ₄, R ₅, R ₆, R ₈Independently be a kind of in hydrogen atom, benzene, biphenyl, naphthalene, anthracene, phenanthrene, pyrene, fluorenes, difluorene, spiral shell fluorenes, carbazole, indole carbazole, three arylamine, pyridine, thiophene, bithiophene, thiophthene, furans, imidazoles, thiodiphenylamine, the iminostilbene group.

5. inverse V type ultra-gees alkali derivant organic electroluminescent compounds according to claim 1 is characterized in that, this structural formula of compound is as follows:

Wherein, X is O, S, in the Se atom one, R ₂, R ₃, R ₄Independently be a kind of in hydrogen atom, benzene, biphenyl, naphthalene, anthracene, phenanthrene, pyrene, fluorenes, difluorene, spiral shell fluorenes, carbazole, indole carbazole, three arylamine, pyridine, thiophene, bithiophene, thiophthene, furans, imidazoles, thiodiphenylamine, the iminostilbene group.

6. according to the described inverse V type ultra-gees alkali derivant organic electroluminescent compounds of claim 2～5, it is characterized in that R ₁Be selected from one of following group A1～A13:

R ₂, R ₄, R ₇Be selected from one of following group A12～A34:

7. inverse V type ultra-gees alkali derivant organic electroluminescent compounds according to claim 6 is characterized in that, this structural formula of compound is as follows:

8. one kind as the application in the luminescent layer in the organic electroluminescence device that the multilayer organic materials is formed of this alkali derivant organic electroluminescent compounds of Λ in the claim 1-type superlattice.

Images