Dibenzoheterocyclic compound and preparation method and application thereof

Abstract

A dibenzoheterocyclic compound having a structure shown in a formula wherein the dibenzoheterocyclic compound has a low LUMO energy level and can be matched with an electron transport material favorable for injection and transport of electrons. The dibenzoheterocyclic compound has hole transport performance. As a light-emitting layer material, the dibenzoheterocyclic compound balances the ratio of electrons to holes in a light-emitting layer increasing the combination probability and improving the light-emitting efficiency of a device. The spatial configuration of the dibenzoheterocyclic compound avoids stacking of material molecules, avoiding generation of high energy excitons due to energy transfer among molecules, reducing annihilation of excitons, and inhibiting efficiency roll-off. The dibenzoheterocyclic compound has thermal stability, so blue light can be emitted efficiently and stably. An organic light-emitting diode contains the dibenzoheterocyclic compound, and a blue light-emitting device with high blue light-emitting efficiency and low driving voltage.

Claims

1. The dibenzoheterocyclic compound having a structure as shown below: ##STR00068##

2. A preparation method of the dibenzoheterocyclic compound according to claim 1, wherein synthesis steps of the dibenzoheterocyclic compound shown in the formula (I) are as follows: taking a compound shown in a formula (A) as a starting material, performing halogenating reaction under the action of a catalyst to obtain an intermediate 1, and enabling the intermediate 1 to react with triphenylphosphine to generate an intermediate 2; enabling the intermediate 2 and a compound shown in a formula (B) to be subjected to Wittig reaction to obtain an intermediate 3; enabling the intermediate 3 and a compound shown in a formula (C) to be subjected to condensation reaction to obtain an intermediate 4; enabling the intermediate 4 to react with a compound of Y.sup.1 and -Y.sup.5 to generate a compound shown in a formula (I′); wherein X.sub.1-X.sub.3 are, each independently, selected from halogen, and R.sub.3-R.sub.10 are, each independently, selected from halogen or hydrogen; a synthesis route of the dibenzoheterocyclic compound shown in the formula (I) is as follows: ##STR00069## ##STR00070##

3. The dibenzoheterocyclic compound according to claim 1, wherein the dibenzoheterocyclic compound is an organic electroluminescent material.

4. An organic light emitting diode, wherein at least one functional layer of the organic light emitting diode contains the dibenzoheterocyclic compound according to claim 1.

5. The organic light emitting diode according to claim 4, wherein the functional layer is a light-emitting layer.

6. The organic light emitting diode according to claim 4, wherein a light-emitting layer material comprises a host material and a guest light-emitting dye, and the guest light-emitting material is the dibenzoheterocyclic compound.

7. The organic light emitting diode according to claim 4, wherein the organic light emitting diode is a blue light-emitting device.

8. A display unit, comprising the organic light emitting diode according to claim 4.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

(1) In order to more clearly illustrate the technical schemes in the detailed description of the invention or the existing technologies, the drawings required in the detailed description of the specific embodiments or the description of the prior art are simply described below. Obviously, the drawings in the following description are some embodiments of the invention, and a person of ordinary skill in the art can also obtain other drawings according to these drawings without any creative work.

(2) FIG. 1 is a structural schematic diagram of an organic light emitting diode according to embodiments 11-19 and a contrast 1 of the invention;

(3) FIG. 2 is a diagram showing the HOMO energy level, the LUMO energy level and theoretical calculation results of ΔE.sub.st of a compound shown in the formula SP-32 provided by an embodiment 5 of the invention.

REFERENCE NUMERALS IN THE DRAWINGS

(4) 1—anode, 2—hole injection layer, 3—hole transport layer, 4—light-emitting layer, 5—electron transport layer, 6—electron injection layer, and 7—cathode.

DETAILED DESCRIPTION

(5) The technical schemes of the invention will be clearly and completely described below. Obviously, the described embodiments are only a part of the embodiments of the invention but not all of the embodiments. Based on the embodiments in the invention, all other embodiments obtained by a person of ordinary skill in the art without creative work belong to the scope of protection of the invention. In addition, the technical features involved in different embodiments of the invention described below can be combined with one other as long as the technical features do not conflict with one other.

(6) In the description of the invention, it should be noted that the terms “first”, “second” and “third” are used for description only and are not intended to indicate or imply relative importance.

(7) The invention can be implemented in many different forms and should not be construed as being limited to the embodiments described herein. Instead, by providing these embodiments, the present disclosure is thorough and complete, the concept of the invention is fully delivered to those skilled in the art, and the invention is limited only by the claims. In the drawings, for clarity, the dimensions and relative dimensions of layers and regions are exaggerated. It should be understood that, when a component, such as a layer, is known as “formed on” or “arranged on” another component, this component can be directly arranged the another component, or an intermediate component can be arranged. On the contrary, when the component is known as “directly formed on” or “directly arranged on” another component, no intervening element is present.

(8) Embodiment 1

(9) This embodiment provides a dibenzoheterocyclic compound having a structure as shown in the formula SP-01 below:

(10) ##STR00019##

(11) A synthesis route of the dibenzoheterocyclic compound shown in the formula SP-01 is as shown below:

(12) ##STR00020## ##STR00021##

(13) A preparation method of the dibenzoheterocyclic compound shown in the formula SP-01 includes the following steps:

(14) 1. Preparation of Intermediate 1-1

(15) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, firstly a compound A-1 (20.548 g, 1.0 equivalent), NBS (N-bromosuccinimide, 19.578 g, 1.1 equivalent), AIBN (azodiisobutyronitrile, 0.821 g, 0.5 mol percent), and carbon tetrachloride (250 ml) were respectively added, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 24 hours; after reaction, water (200 ml) was added to quench the reaction. After extraction with ethyl acetate (3*200 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/10) to obtain the intermediate 1-1 (21.044 g, yield: 74%).

(16) 2. Preparation of Intermediate 2-1

(17) In a dry, nitrogen-flushed 500 ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, firstly the intermediate 1-1 (20.000 g, 1.0 equivalent) and triphenylphosphine (19.369 g, 1.05 equivalent), and toluene (250 ml) were respectively added, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 18 hours; after reaction, the mixture was filtered, and then, the obtained solid was cleaned with hexane (3*80 ml) to obtain a crude product (38.231 g) of the intermediate 2-1.

(18) 3. Preparation of Intermediate 3-1

(19) In a dry, nitrogen-flushed 500 ml double-neck round-bottom flask, equipped with a magnetic stirring bar, firstly, the intermediate 2-1 (35.000 g, 1.0 equivalent), potassium tert-butoxide (21.553 g, 3.0 equivalent), and tetrahydrofuran (150 ml) were respectively added, the mixture was stirred for 10 minutes at 0° C., subsequently, 2-bromo-6-chlorobenzaldehyde (a compound shown in the formula B-1, 14.051 g, 1.0 equivalent) dissolved in tetrahydrofuran (100 ml) was added dropwise, and finally, the reaction was stirred for 24 hours at room temperature; after reaction, water (50 ml) was added to quench the reaction. After extraction with ethyl ether (3*300 ml), the combined extraction liquids were dried over magnesium sulfate, filtered and concentrated under vacuum. The crude product was purified by column chromatography (ethyl acetate/hexane, 1/75) to obtain the intermediate 3-1 (23.969 g, yield: 92%).

(20) 4. Preparation of Intermediate 4-1

(21) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, firstly, the intermediate 3-1 (20.346 g, 1.0 equivalent) and anhydrous tetrahydrofuran (180 ml) were added, the mixture was stirred for 10 minutes at −78° C., subsequently, 2.5 M butyl lithium dissolved in hexane (43 ml, 2.15 equivalent) was added dropwise and the reaction was stirred for 30 minutes, N,N,N′,N′-tetramethyl-1,2-ethanediamine (17 ml, 2.3 equivalent) was added dropwise and the reaction was stirred for 2 hours, and finally, dimethyldichlorosilane (the compound shown in the formula C-1, 6.6 ml, 1.1 equivalent) was added dropwise; after reaction a saturated sodium bicarbonate aqueous solution (50 ml) was added to quench the reaction. After extraction with ethyl acetate (3*150 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/30) to obtain the intermediate 4-1 (9.616 g, yield: 63%).

(22) 5. Preparation of Dibenzoheterocyclic Compound Having Structure Shown in Formula SP-01

(23) In a dry, nitrogen-flushed 100-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, firstly, the intermediate 4-1 (3.053 g, 1.0 equivalent), N-(1-naphthyl)-aniline (4.495 g, 2.05 equivalent), Pd.sub.2(dba).sub.3 (0.275 g, 3 mol percent), potassium tert-butoxide (2.018 g, 2.1 equivalent), and anhydrous toluene (40 ml) were respectively added, the mixture was stirred for 10 minutes, subsequently, tert-butyl phosphate dissolved in toluene (0.03 M, 10 ml) was added dropwise, and finally, the mixture was heated refluxly for 6 hours; after reaction, water (30 ml) was added to quench the reaction. After extraction with ethyl acetate (3*20 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/20) to obtain the compound SP-01 (6.441 g, yield: 96%).

(24) Elemental analysis: (C.sub.48H.sub.38N.sub.2Si) theoretical values: C, 85.93; H, 5.71; N, 4.18; Si, 4.19; measured values: C, 85.81; H, 5.74; N, 4.21; Si, 4.24; HRMS (ESI) m/z (M+): theoretical value: 670.9310; measured value: 679.9313.

(25) Embodiment 2

(26) This embodiment provides a dibenzoheterocyclic compound having a structure as shown in the formula SP-02 below:

(27) ##STR00022##

(28) A synthesis route of the dibenzoheterocyclic compound shown in the formula SP-02 is as shown below:

(29) ##STR00023## ##STR00024##

(30) A preparation method of the dibenzoheterocyclic compound shown in the formula SP-02 includes the following steps:

(31) 1. Preparation of Intermediate 1-2

(32) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, firstly a compound A-2 (20.548 g, 1.0 equivalent), NBS (N-bromosuccinimide, 19.578 g, 1.1 equivalent), AIBN (azodiisobutyronitrile, 0.821 g, 0.5 mol percent), and carbon tetrachloride (250 ml) were respectively added, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 24 hours; after reaction, water (200 ml) was added to quench the reaction. After extraction with ethyl acetate (3*200 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/10) to obtain the intermediate 1-2 (20.191 g, yield: 71%).

(33) 2. Preparation of Intermediate 2-2

(34) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, firstly, the intermediate 1-2 (20.000 g, 1.0 equivalent), triphenylphosphine (19.369 g, 1.05 equivalent), and toluene (250 ml) were respectively added, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 18 hours; after reaction, the mixture was filtered, and the obtained solid was cleaned with hexane (3*80 ml) to obtain a crude product (38.466 g) of the intermediate 2-2.

(35) 3. Preparation of Intermediate 3-2

(36) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar, firstly, the intermediate 2-2 (35.000 g, 1.0 equivalent), potassium tert-butoxide (21.553 g, 3.0 equivalent), and tetrahydrofuran (150 ml) were respectively added, the reaction was stirred for 10 minutes at 0° C., subsequently, 2-bromo-5-chlorobenzaldehyde (a compound shown in the formula B-2, 14.051 g, 1.0 equivalent) dissolved in tetrahydrofuran (100 ml) was added dropwise, and finally, the reaction was stirred for 24 hours at room temperature; after reaction, water (50 ml) was added to quench the reaction. After extraction with ethyl ether (3*300 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/70) to obtain the intermediate 3-2 (23.187 g, yield: 89%).

(37) 4. Preparation of Intermediate 4-2

(38) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, firstly, the intermediate 3-2 (20.346 g, 1.0 equivalent) and anhydrous tetrahydrofuran (180 ml) were added, the mixture was stirred for 10 minutes at −78° C., subsequently, 2.5 M butyl lithium dissolved in hexane (43 ml, 2.15 equivalent) was added dropwise, and the reaction was stirred for 30 minutes, N,N,N′,N′-tetramethyl-1,2-ethanediamine (17 ml, 2.3 equivalent) was added dropwise and the reaction was stirred for 2 hours, and finally, dimethyldichlorosilane (the compound shown in the formula C-1, 6.6 ml, 1.1 equivalent) was added dropwise; a saturated sodium bicarbonate aqueous solution (50 ml) was added to quench the reaction. After extraction with ethyl acetate (3*150 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/30) to obtain the intermediate 4-2 (7.784 g, yield: 51%).

(39) 5. Preparation of Dibenzoheterocyclic Compound Shown in Formula SP-02

(40) In a dry, nitrogen-flushed 100-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 4-2 (3.053 g, 1.0 equivalent), N-(1-naphthyl)-aniline (4.495 g, 2.05 equivalent), Pd.sub.2(dba).sub.3 (0.275 g, 3 mol percent), potassium tert-butoxide (2.018 g, 2.1 equivalent), and anhydrous toluene (40 ml) were respectively added firstly, the mixture was stirred for 10 minutes, subsequently, tert-butyl phosphate dissolved in toluene (0.03 M, 10 ml) was added, and finally, the mixture was heated refluxly for 6 hours; water (30 ml) was added to quench the reaction. After extraction with ethyl acetate (3*20 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/20) to obtain the compound SP-02 (5.166 g, yield: 77%).

(41) Elemental analysis: (C.sub.48H.sub.38N.sub.2Si) theoretical values: C, 85.93; H, 5.71; N, 4.18; Si, 4.19; measured values: C, 85.91; H, 5.72; N, 4.16; Si, 4.21; HRMS (ESI) m/z (M.sup.+): theoretical value: 670.9310; measured value: 679.9311.

(42) Embodiment 3

(43) This embodiment provides a dibenzoheterocyclic compound having a structure as shown in the formula SP-03 below:

(44) ##STR00025##

(45) A synthesis route of the dibenzoheterocyclic compound shown in the formula SP-03 is as shown below:

(46) ##STR00026## ##STR00027##

(47) A preparation method of the dibenzoheterocyclic compound shown in the formula SP-03 includes the following steps:

(48) 1. Preparation of Intermediate 1-3

(49) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, a compound A-3 (20.548 g, 1.0 equivalent), NBS (N-bromosuccinimide, 19.578 g, 1.1 equivalent), AIBN (azodiisobutyronitrile, 0.821 g, 0.5 mol percent) and carbon tetrachloride (250 ml) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 24 hours; after reaction, water (200 ml) was added to quench the reaction. After extraction with ethyl acetate (3*200 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/10) to obtain the intermediate 1-3 (23.604 g, yield: 83%).

(50) 2. Preparation of Intermediate 2-3

(51) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 1-3 (20.000 g, 1.0 equivalent), triphenylphosphine (19.369 g, 1.05 equivalent), and toluene (250 ml) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 18 hours; and after reaction, the mixture was filtered, and then, the obtained solid was cleaned with hexane (3*80 ml) to obtain a crude product (38.316 g) of the intermediate 2-3.

(52) 3. Preparation of Intermediate 3-3

(53) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar, the intermediate 2-3 (35.000 g, 1.0 equivalent), potassium tert-butoxide (21.553 g, 3.0 equivalent), and tetrahydrofuran (150 ml) were respectively added firstly, the mixture was stirred for 10 minutes at 0° C., subsequently, 2-bromo-4-chlorobenzaldehyde (a compound shown in the formula B-3, 14.051 g, 1.0 equivalent) dissolved in tetrahydrofuran (100 ml) was added dropwise, and finally, the reaction was stirred for 24 hours at room temperature; after reaction, water (50 ml) was added to quench the reaction. After extraction with ethyl ether (3*300 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/80) to obtain the intermediate 3-3 (24.750 g, yield: 89%).

(54) 4. Preparation of Intermediate 4-3

(55) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 3-3 (20.346 g, 1.0 equivalent) and anhydrous tetrahydrofuran (180 ml) were added firstly, the mixture was stirred for 10 minutes at −78° C., subsequently, 2.5 M butyl lithium dissolved in hexane (43 ml, 2.15 equivalent) was added dropwise and the reaction was stirred for 30 minutes, N,N,N′,N′-tetramethyl-1,2-ethanediamine (17 ml, 2.3 equivalent) was added dropwise and the reaction was stirred for 2 hours, and finally, dimethyldichlorosilane (the compound shown in the formula C-1, 6.6 ml, 1.1 equivalent) was added dropwise; after reaction, a saturated sodium bicarbonate aqueous solution (50 ml) was added to quench the reaction. After extraction with ethyl acetate (3*150 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/30) to obtain the intermediate 4-3 (10.531 g, yield: 69%).

(56) 5. Preparation of Dibenzoheterocyclic Compound Shown in Formula SP-03

(57) In a dry, nitrogen-flushed 100-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 4-3 (3.053 g, 1.0 equivalent), N-(1-naphthyl)-aniline (4.495 g, 2.05 equivalent), Pd.sub.2(dba).sub.3 (0.275 g, 3 mol percent), potassium tert-butoxide (2.018 g, 2.1 equivalent) and anhydrous toluene (40 ml) were respectively added firstly, the mixture was stirred for 10 minutes, subsequently, tert-butyl phosphate dissolved in toluene (0.03 M, 10 ml) was added, and finally, the mixture was heated refluxly for 6 hours; after reaction, water (30 ml) was added to quench the reaction. After extraction with ethyl acetate (3*20 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/25) to obtain the compound SP-03 (6.441 g, yield: 95%).

(58) Elemental analysis: (C.sub.48H.sub.38N.sub.2Si) theoretical values: C, 85.93; H, 5.71; N, 4.18; Si, 4.19; measured values: C, 85.96; H, 5.72; N, 4.16; Si, 4.16; HRMS (ESI) m/z (M.sup.+): theoretical value: 670.9310; measured value: 679.9313.

(59) Embodiment 4

(60) This embodiment provides a dibenzoheterocyclic compound having a structure as shown in the formula SP-04 below:

(61) ##STR00028##

(62) A synthesis route of the dibenzoheterocyclic compound shown in the formula SP-04 is as shown below:

(63) ##STR00029## ##STR00030##

(64) A preparation method of the dibenzoheterocyclic compound shown in the formula SP-04 includes the following steps:

(65) 1. Preparation of Intermediate 1-4

(66) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, a compound A-4 (20.548 g, 1.0 equivalent), NBS (N-bromosuccinimide, 19.578 g, 1.1 equivalent), AIBN (azodiisobutyronitrile, 0.821 g, 0.5 mol percent), and carbon tetrachloride (250 ml) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 24 hours; after reaction, water (200 ml) was added to quench the reaction. After extraction with ethyl acetate (3*200 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/10) to obtain the intermediate 1-4 (23.867 g, yield: 65%).

(67) 2. Preparation of Intermediate 2-4

(68) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 1-4 (20.000 g, 1.0 equivalent), triphenylphosphine (19.369 g, 1.05 equivalent), and toluene (250 ml) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 18 hours; and after reaction, the mixture was filtered, and then, the obtained solid was cleaned with hexane (3*80 ml) to obtain a crude product (37.831 g) of the intermediate 2-4.

(69) 3. Preparation of Intermediate 3-4

(70) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar, the intermediate 2-4 (35.000 g, 1.0 equivalent), potassium tert-butoxide (21.553 g, 3.0 equivalent), and tetrahydrofuran (150 ml) were respectively added firstly, the mixture was stirred for 10 minutes at 0° C., subsequently, 2-bromo-3-chlorobenzaldehyde (a compound shown in the formula B-4, 14.051 g, 1.0 equivalent) dissolved in tetrahydrofuran (100 ml) was added dropwise, and finally, the reaction was stirred for 24 hours at room temperature; after reaction, water (50 ml) was added to quench the reaction. After extraction with ethyl ether (3*300 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/75) to obtain the intermediate 3-4 (22.525 g, yield: 81%).

(71) 4. Preparation of Intermediate 4-4

(72) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 3-4 (20.346 g, 1.0 equivalent) and anhydrous tetrahydrofuran (180 ml) were added firstly, the mixture was stirred for 10 minutes at −78° C., subsequently, 2.5 M butyl lithium dissolved in hexane (43 ml, 2.15 equivalent) was added dropwise and the reaction was stirred for 30 minutes, N,N,N′,N′-tetramethyl-1,2-ethanediamine (17 ml, 2.3 equivalent) was added dropwise and the reaction was stirred for 2 hours, and finally, dimethyldichlorosilane (the compound shown in the formula C-1, 6.6 ml, 1.1 equivalent) was added dropwise; after reaction, a saturated sodium bicarbonate aqueous solution (50 ml) was added to quench the reaction. After extraction with ethyl acetate (3*150 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/30) to obtain the intermediate 4-4 (7.173 g, yield: 47%).

(73) 5. Preparation of Dibenzoheterocyclic Compound Having Structure as Shown in Formula SP-04

(74) In a dry, nitrogen-flushed 100-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 4-4 (3.053 g, 1.0 equivalent), N-(1-naphthyl)-aniline (4.495 g, 2.05 equivalent), Pd.sub.2(dba).sub.3 (0.275 g, 3 mol percent) and potassium tert-butoxide (2.018 g, 2.1 equivalent), and anhydrous toluene (40 ml) were respectively added firstly, the mixture was stirred for 10 minutes, subsequently, tert-butyl phosphate dissolved in toluene (0.03 M, 10 ml) was added, and finally, the mixture was heated refluxly for 6 hours; water (30 ml) was added to quench the reaction. After extraction with ethyl acetate (3*20 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/20) to obtain the compound SP-04 (5.288 g, yield: 78%).

(75) Elemental analysis: (C.sub.48H.sub.38N.sub.2Si) theoretical values: C, 85.93; H, 5.71; N, 4.18; Si, 4.19; measured values: C, 85.89; H, 5.75; N, 4.21; Si, 4.15; HRMS (ESI) m/z (M.sup.+): theoretical value: 670.9310; measured value: 679.9308.

(76) Embodiment 5

(77) This embodiment provides a dibenzoheterocyclic compound

(78) as shown in the formula SP-32 below:

(79) ##STR00031##

(80) A synthesis route of the dibenzoheterocyclic compound shown in the formula SP-32 is as shown below:

(81) ##STR00032## ##STR00033##

(82) A preparation method of the dibenzoheterocyclic compound shown in the formula SP-32 includes the following steps:

(83) 1. Preparing an intermediate 3-3 by the method provided by the embodiment 3.

(84) 2. Preparing an intermediate 4-5:

(85) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 3-3 (20.346 g, 1.0 equivalent) and anhydrous tetrahydrofuran (180 ml) were added firstly, the mixture was stirred for 10 minutes at −78° C., subsequently, 2.5 M butyl lithium dissolved in hexane (43 ml, 2.15 equivalent) was added dropwise and the reaction was stirred for 30 minutes, N,N,N′,N′-tetramethyl-1,2-ethanediamine (17 ml, 2.3 equivalent) was added dropwise and the reaction was stirred for 2 hours, and finally, diethyldichlorosilane (a compound shown in the formula C-2, 8.2 ml, 1.1 equivalent) was added dropwise; after reaction, a saturated sodium bicarbonate aqueous solution (50 ml) was added to quench the reaction. After extraction with ethyl acetate (3*150 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/30) to obtain the intermediate 4-5 (10.333 g, yield: 62%).

(86) 3. Preparing the dibenzoheterocyclic compound shown in the formula SP-32:

(87) In a dry, nitrogen-flushed 100-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 4-5 (3.333 g, 1.0 equivalent), N-(1-naphthyl)-aniline (4.495 g, 2.05 equivalent), Pd.sub.2(dba).sub.3 (0.275 g, 3 mol percent), potassium tert-butoxide (2.018 g, 2.1 equivalent), and anhydrous toluene (40 ml) were respectively added firstly, the mixture was stirred for 10 minutes, subsequently, tert-butyl phosphate dissolved in toluene (0.03 M, 10 ml) was added, and finally, the mixture was heated refluxly for 6 hours; after reaction, water (30 ml) was added to quench the reaction. After extraction with ethyl acetate (3*20 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/20) to obtain the compound SP-32 (6.774 g, yield: 97%).

(88) Elemental analysis: (C.sub.50H.sub.42N.sub.2Si) theoretical values: C, 85.92; H, 6.06; N, 4.01; Si, 4.02; measured values: C, 85.88; H, 6.07; N, 4.04; Si, 4.01; HRMS (ESI) m/z (M.sup.+): theoretical value: 698.3117; measured value: 698.3112.

(89) Embodiment 6

(90) This embodiment provides a dibenzoheterocyclic compound having a structure as shown in the formula SP-34 below:

(91) ##STR00034##

(92) A synthesis route of the dibenzoheterocyclic compound shown in the formula SP-34 is as shown below:

(93) ##STR00035## ##STR00036##

(94) A preparation method of the dibenzoheterocyclic compound shown in the formula SP-34 includes the following steps:

(95) 1. Preparing an intermediate 4-5 by the method provided by the embodiment 5.

(96) 2. Preparing the dibenzoheterocyclic compound shown in the formula SP-34:

(97) In a dry, nitrogen-flushed 100-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 4-5 (3.333 g, 1.0 equivalent), N,N-di-(1,3,5-trimethyl)amine (5.194 g, 2.05 equivalent), Pd.sub.2(dba).sub.3 (0.275 g, 3 mol percent), potassium tert-butoxide (2.018 g, 2.1 equivalent), and anhydrous toluene (40 ml) were respectively added firstly, the mixture was stirred for 10 minutes, subsequently, tert-butyl phosphate dissolved in toluene (0.03 M, 10 ml) was added, and finally, the mixture was heated refluxly for 6 hours; water (30 ml) was added to quench the reaction. After extraction with ethyl acetate (3*20 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/20) to obtain the compound SP-34 (6.828 g, yield: 89%).

(98) Elemental analysis: (C.sub.54H.sub.62N.sub.2Si) theoretical values: C, 84.54; H, 8.15; N, 3.65; Si, 3.66; measured values: C, 84.55; H, 8.12; N, 3.69; Si, 3.64; HRMS (ESI) m/z (M.sup.+): theoretical value: 767.1890; measured value: 767.1887.

(99) Embodiment 7

(100) This embodiment provides a dibenzoheterocyclic compound having a structure as shown in the formula SP-36 below:

(101) ##STR00037##

(102) A synthesis route of the dibenzoheterocyclic compound shown in the formula SP-36 is as shown below:

(103) ##STR00038## ##STR00039##

(104) A preparation method of the dibenzoheterocyclic compound shown in the formula SP-36 includes the following steps:

(105) 1. Preparing an intermediate 4-5 by the method provided by the embodiment 5.

(106) 2. Preparing the dibenzoheterocyclic compound shown in the formula SP-36:

(107) In a dry, nitrogen-flushed 100-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 4-5 (3.333 g, 1.0 equivalent), N,N-di-(4-biphenyl)amine (6.589 g, 2.05 equivalent), Pd.sub.2(dba).sub.3 (0.275 g, 3 mol percent), potassium tert-butoxide (2.018 g, 2.1 equivalent), and anhydrous toluene (40 ml) were respectively added firstly, the mixture was stirred for 10 minutes, subsequently, tert-butyl phosphate dissolved in toluene (0.03 M, 10 ml) was added, and finally, the mixture was heated refluxly for 6 hours; water (30 ml) was added to quench the reaction. After extraction with ethyl acetate (3*20 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/20) to obtain the compound SP-36 (8.491 g, yield: 94%).

(108) Elemental analysis: (C.sub.66H.sub.54N.sub.2Si) theoretical values: C, 87.76; H, 6.03; N, 3.10; Si, 3.11; measured values: C, 87.71; H, 6.04; N, 3.09; Si, 3.16; HRMS (ESI) m/z (M.sup.+): theoretical value: 903.2570; measured value: 903.2566.

(109) Embodiment 8

(110) This embodiment provides a dibenzoheterocyclic compound having a structure as shown in the formula SP-38 below:

(111) ##STR00040##

(112) A synthesis route of the dibenzoheterocyclic compound shown in the formula SP-38 is as shown below:

(113) ##STR00041## ##STR00042##

(114) A preparation method of the dibenzoheterocyclic compound shown in the formula SP-38 includes the following steps:

(115) 1. Preparing an intermediate 4-5 by the method provided by the embodiment 5.

(116) 2. Preparing the dibenzoheterocyclic compound shown in the formula SP-38:

(117) In a dry, nitrogen-flushed 100-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 4-5 (3.333 g, 1.0 equivalent), 4-(N,N-diphenylamino)phenylboric acid (6.650 g, 2.3 equivalent), Pd(PPh.sub.3).sub.4 (0.578 g, 5 mol percent), sodium carbonate (2.649 g, 2.5 equivalent), anhydrous toluene (40 ml) and water (4 ml) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 18 hours; water (30 ml) was added to quench the reaction. After extraction with ethyl acetate (3*20 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/20) to obtain the compound SP-38 (5.858 g, yield: 78%).

(118) Elemental analysis: (C.sub.54H.sub.46N.sub.2Si) theoretical values: C, 86.36; H, 6.17; N, 3.73; Si, 3.74; measured values: C, 86.39; H, 6.18; N, 3.71; Si, 3.72; HRMS (ESI) m/z (M.sup.+): theoretical value: 751.0610; measured value: 751.0613.

(119) Embodiment 9

(120) This embodiment provides a dibenzoheterocyclic compound having a structure as shown in the formula SP-55 below:

(121) ##STR00043##

(122) A synthesis route of the dibenzoheterocyclic compound shown in the formula SP-55 is as shown below:

(123) ##STR00044## ##STR00045##

(124) A preparation method of the dibenzoheterocyclic compound shown in the formula SP-55 includes the following steps:

(125) 1. Preparing an intermediate 4-7 by the method provided by the embodiment 5.

(126) 2. Preparing the dibenzoheterocyclic compound shown in the formula SP-55:

(127) In a dry, nitrogen-flushed 100-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 4-5 (3.333 g, 1.0 equivalent), 4-methoxyphenylboric acid (1.520 g, 1.0 equivalent), Pd(PPh.sub.3).sub.4 (0.578 g, 5 mol percent), sodium carbonate (2.649 g, 2.5 equivalent), anhydrous toluene (40 ml) and water (4 ml) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 8 hours; 4-cyanophenylboric acid (1.616 g, 1.1 equivalent) was added after the reaction temperature cooled and the mixture was stirred for 10 minutes, and then, the mixture was heated refluxly for 12 hours; after reaction, water (30 ml) was added to quench the reaction. After extraction with ethyl acetate (3*20 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/20) to obtain the compound SP-55 (3.396 g, yield: 72%).

(128) Elemental analysis: (C.sub.32H.sub.29NOSi) theoretical values: C, 81.49; H, 6.20; N, 2.97; 0, 3.39; Si, 5.95; m/z: 471.2018 (100.0%), 472.2052 (34.6%), 473.2086 (5.8%), 472.2014 (5.1%), 473.1987 (3.3%), 473.2048 (1.8%), 474.2020 (1.2%); HRMS (ESI) m/z (M.sup.+): theoretical value: 471.2018; measured value: 471.6750.

(129) Embodiment 10

(130) This embodiment provides a dibenzoheterocyclic compound having a structure as shown in the formula SP-56 below:

(131) ##STR00046##

(132) A synthesis route of the dibenzoheterocyclic compound shown in the formula SP-56 is as shown below:

(133) ##STR00047## ##STR00048##

(134) A preparation method of the dibenzoheterocyclic compound shown in the formula SP-56 includes the following steps:

(135) 1. Preparing an intermediate 4-5 by the method provided by the embodiment 5.

(136) 2. Preparing the dibenzoheterocyclic compound shown in the formula SP-56:

(137) In a dry, nitrogen-flushed 100-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 4-5 (3.333 g, 1.0 equivalent), 4-methoxyphenylboric acid (3.495 g, 2.3 equivalent), Pd(PPh.sub.3).sub.4 (0.578 g, 5 mol percent), sodium carbonate (2.649 g, 2.5 equivalent), anhydrous toluene (40 ml) and water (4 ml) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 18 hours; water (30 ml) was added to quench the reaction. After extraction with ethyl acetate (3*20 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/20) to obtain the compound SP-56 (5.858 g, yield: 86%).

(138) Elemental analysis: (C.sub.32H.sub.32O.sub.2Si) theoretical values: C, 80.63; H, 6.77; 0, 6.71; Si, 5.89; measured values: C, 80.60; H, 6.72; 0, 6.75; Si, 5.93; HRMS (ESI) m/z (M.sup.+): theoretical value: 476.6910; measured value: 476.6907.

(139) Embodiment 11

(140) This embodiment provides a dibenzoheterocyclic compound having a structure as shown in the formula SP-42 below:

(141) ##STR00049##

(142) A synthesis route of the dibenzoheterocyclic compound shown in the formula SP-42 is as shown below:

(143) ##STR00050## ##STR00051## ##STR00052## ##STR00053## ##STR00054##

(144) A preparation method of the dibenzoheterocyclic compound shown in the formula SP-56 includes the following steps:

(145) 1. Preparing an intermediate 3-3 by the method provided by the embodiment 3.

(146) 2. Preparing an intermediate 4-6:

(147) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate 3-3 (20.346 g, 1.0 equivalent), and anhydrous tetrahydrofuran (180 ml) were added firstly, the mixture was stirred for 10 minutes at −78° C., subsequently, 2.5 M butyl lithium dissolved in (43 ml, 2.15 equivalent) was added dropwise and the reaction was stirred for 30 minutes, N,N,N′,N′-tetramethyl-1,2-ethanediamine (17 ml, 2.3 equivalent) was added dropwise and the reaction was stirred for 2 hours, and finally, dimethoxydichlorosilane (8.858 g, 1.1 equivalent, a compound as shown in the formula C-3) was added dropwise; after reaction, a saturated sodium bicarbonate aqueous solution (50 ml) was added to quench the reaction. After extraction with ethyl acetate (3*150 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum.

(148) The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/25) to obtain the intermediate 4-6 (8.600 g, yield: 51%).

(149) 3. Preparing an intermediate I′:

(150) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, firstly the intermediate 4-6 (8.432 g, 1.0 equivalent), 4-(N,N-diphenylamino)phenylboric acid (18.238 g, 2.3 equivalent), Pd(PPh.sub.3).sub.4 (1.444 g, 5 mol percent) and sodium carbonate (6.624 g, 2.5 equivalent), anhydrous toluene (200 ml) and water (20 ml) were respectively added, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 18 hours; after the reaction was cooing down, water (150 ml) was added to quench the reaction. After extraction with ethyl acetate (3*200 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/20) to obtain the intermediate I′ (15.817 g, yield: 78%).

(151) 4. Preparing an intermediate I″:

(152) In a dry, nitrogen-flushed 500-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate I′ (6.071 g, 1.0 equivalent) was added firstly, subsequently, bromine water (2.4 ml, 5.2 equivalent) and hydrobromic acid (150 ml) were respectively added, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 6 hours; water (120 ml) was added to quench the reaction. After extraction with ethyl acetate (3*150 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/20) to obtain the intermediate I″ (11.010 g, yield: 63%).

(153) 5. Preparing an intermediate I′″-1:

(154) In a dry, nitrogen-flushed 250-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate I″ (9.709 g, 1.0 equivalent), potassium hydroxide (1.683 g, 3.0 equivalent), and 1,2-dimethoxyethane (100 ml) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 4 hours; after reaction, furan (1.3 ml, 1.8 equivalent) was added, and then, the mixture was heated refluxly for 12 hours; after reaction, water (50 ml) was added to quench the reaction. After extraction with ethyl acetate (3*80 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/25) to obtain the intermediate I′″-1 (4.386 g, yield: 50%).

(155) 6. Preparing an intermediate I′″-2:

(156) In a dry, nitrogen-flushed 100-ml double-neck round-bottom flask, equipped with a magnetic stirring bar, the intermediate I′″-1 (3.509 g, 1.0 equivalent), activated carbon supported palladium (5%, 0.213 g, 2.5 mol percent), and ethyl acetate (40 ml) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, hydrogen gas was added and the reaction was stirred for 8 hours at room temperature; water (30 ml) was added. After extraction with ethyl acetate (3*30 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/25) to obtain the intermediate I′″-2 (3.306 g, yield: 94%).

(157) 7. Preparing the dibenzoheterocyclic compound shown in the formula SP-42:

(158) In a dry, nitrogen-flushed 50-ml double-neck round-bottom flask, equipped with a magnetic stirring bar and a reflux tube, the intermediate I′″-2 (2.638 g, 1.0 equivalent), p-toluenesulfonic acid (1.033 g, 2.0 equivalent), and toluene (25 ml) were respectively added firstly, the mixture was stirred for 10 minutes, and finally, the mixture was heated refluxly for 16 hours; water (15 ml) was added. After extraction with ethyl acetate (3*20 ml), the combined extraction liquids were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by means of column chromatography (ethyl acetate/hexane, 1/30) to obtain the compound SP-42 (2.506 g, yield: 97%).

(159) Elemental analysis: (C.sub.60H.sub.52N.sub.2O.sub.2Si) theoretical values: C, 83.68; H, 6.09; N, 3.25; measured values: C, 83.66; H, 6.10; N, 3.28; HRMS (ESI) m/z (M.sup.+): theoretical value: 860.3798; measured value: 860.3792.

(160) Embodiment 12

(161) This embodiment provides an organic light-emitting device. As shown in FIG. 1, the organic light-emitting device includes an anode 1, a hole injection layer 2, a hole transport layer 3, a light-emitting layer 4, an electron transport layer 5, an electron injection layer 6 and a cathode 7 which are sequentially stacked on a substrate.

(162) In the organic light-emitting device, the anode is made of an ITO material; the cathode 7 is made of metal Al;

(163) the hole injection layer 2 is made from PEDOT:PSS, and the PEDOT:PSS has a chemical structure as shown below:

(164) ##STR00055##

(165) the hole transport layer 3 is made from NPB, and the NPB has a chemical structure as shown below:

(166) ##STR00056##

(167) the electron transport layer 5 is made from TPBI, and the TPBI has the chemical structure as shown below:

(168) ##STR00057##

(169) the electron injection layer 6 is formed by doping TPBI with an electron injection material LiF;

(170) a light-emitting material of the light-emitting layer 32 in the organic light emitting diode is selected from the dibenzoheterocyclic compound shown in the formula SP-01:

(171) ##STR00058##
and

(172) the organic light-emitting device forms the following specific structure: ITO (anode)/PEDOT:PSS (hole injection layer, 30 nm)/NPB (hole transport layer, 40 nm)/SP-01 (blue light-emitting layer, 40 nm)/TPBI (electron injection layer, 35 nm)/TPBI:LiF (electron transport layer, 40 nm) aluminum (cathode, 5 nm/150 nm).

(173) The light-emitting layer material is selected from the dibenzoheterocyclic compound SP-01, light color coordinates are positioned in a blue light-emitting region, and a blue light-emitting device can be obtained. Because of the existence of the diphenylethylene group in the mother nucleus structure, the compound SP-01 has a low LUMO energy level (−1.35 eV), thereby being favorable for matching the energy level of the electron transport layer, and promoting injection and transport of electrons. Meanwhile, the dibenzoheterocyclic compound SP-01 is linked with the substituent group

(174) ##STR00059##
of an electron donor, material molecules have good hole transport performance, and the HOMO energy level is suitable for matching an adjacent hole transport layer, thereby being favorable for balancing electrons and holes in the light-emitting layer, increasing the combination probability of electrons and holes, and improving the blue light-emitting efficiency of the OLED. The spatial configuration of the dibenzoheterocyclic compound SP-01 is a butterfly configuration, thereby avoiding the generation of high energy excitons caused by stacking of the material molecules, effectively reducing the annihilation of the excitons in the light-emitting layer, avoiding the efficiency roll-off of the blue light-emitting device, preventing deep blue color coordinate drift, and further obtaining the blue light-emitting device with high light-emitting stability. Proper HOMO and LUMO energy levels of the dibenzoheterocyclic compound SP-01 are favorable for lowering the potential barrier needing to be overcome by transporting electrons and holes to the light-emitting layer, and further lowering the working voltage of the device. On the other hand, the dibenzoheterocyclic compound shown in SP-01 has high thermal decomposition temperature, high thermal stability and morphological stability and excellent film formation performance; and as a light-emitting layer material, the compound is not easy to decompose and crystallize, thereby further improving the performance and the light-emitting efficiency of the OLED.

(175) As an alternative embodiment, the guest light-emitting material of the light-emitting layer can also be selected from any dibenzoheterocyclic compound shown in the formula (SP-02) to the formula (SP-65).

(176) As an alternative embodiment, the guest light-emitting material of the light-emitting layer can also be selected from any other dibenzoheterocyclic compound having a chemical structure shown in the general formula (I).

(177) Embodiment 13

(178) This embodiment provides an organic light-emitting device, which is different from the organic light-emitting device provided by the embodiment 12 only in that the light-emitting layer material is selected from the dibenzoheterocyclic compound having a structure shown below:

(179) ##STR00060##

(180) Embodiment 14

(181) This embodiment provides an organic light-emitting device, which is different from the organic light-emitting device provided by the embodiment 12 only in that the light-emitting layer material is selected from the dibenzoheterocyclic compound having a structure shown below:

(182) ##STR00061##

(183) Embodiment 15

(184) This embodiment provides an organic light-emitting device, which is different from the organic light-emitting device provided by the embodiment 12 only in that the light-emitting layer material is selected from the dibenzoheterocyclic compound having a structure shown below:

(185) ##STR00062##

(186) Embodiment 16

(187) This embodiment provides an organic light-emitting device, which is different from the organic light-emitting device provided by the embodiment 12 only in that the light-emitting layer material is selected from the dibenzoheterocyclic compound having a structure shown below:

(188) ##STR00063##

(189) Embodiment 17

(190) This embodiment provides an organic light-emitting device, which is different from the organic light-emitting device provided by the embodiment 12 only in that the light-emitting layer material is selected from the dibenzoheterocyclic compound having a structure shown below:

(191) ##STR00064##

(192) Embodiment 18

(193) This embodiment provides an organic light-emitting device, which is different from the organic light-emitting device provided by the embodiment 12 only in that the light-emitting layer material is selected from the dibenzoheterocyclic compound having a structure shown below:

(194) ##STR00065##

(195) Embodiment 19

(196) This embodiment provides an organic light-emitting device, which is different from the organic light-emitting device provided by the embodiment 12 in that the light-emitting layer material is selected from the dibenzoheterocyclic compound having a structure shown below:

(197) ##STR00066##

(198) Contrast 1

(199) This contrast provides an organic light-emitting device, which is different from the organic light-emitting device provided by the embodiment 12 only in that the light-emitting layer material is selected from the compound having a structure shown below:

(200) ##STR00067##

(201) Test Case 1

(202) 1. Measurement of Thermal Decomposition Temperature (T.sub.d) of Dibenzoheterocyclic Compound

(203) A thermal gravimetric analyzer (TGA) is used for testing the thermal decomposition temperature of the material of the invention in the range from room temperature to 600° C. at a ramping rate of 10° C./min under nitrogen atmosphere, the temperature with the weight loss of 0.5% is defined as the thermal decomposition temperature.

(204) 2. Measurement of HOMO Energy Level and LUMO Energy Level of Dibenzoheterocyclic Compound

(205) An electrochemical workstation is used for testing the HOMO and LUMO energy levels of the material of the invention through a cyclic voltammetry (CV), a platinum filament (PT) is used as a counter electrode, and silver/silver chloride (Ag/AgCl) is used as a reference electrode. Under the nitrogen atmosphere, a test is carried out in a dichloromethane electrolyte containing 0.1 M tetrabutylammonium hexafluorophosphate at a scanning rate of 100 mV/s, potential calibration is performed by ferrocene, and an absolute HOMO energy level of the potential of the ferrocene in a vacuum state is set to −4.8 eV:
HOMO=−[E.sub.onset.sup.ox−E.sub.Fc/Fc++4.8]eV;
LUMO=−[E.sub.onset.sup.red−E.sub.Fc/Fc++4.8]eV.

(206) TABLE-US-00001 TABLE 1 Compound SP-01 SP-02 SP-03 SP-04 SP-32 SP-34 SP-36 SP-38 SP-42 SP-55 SP-56 T.sub.d (° C.) 427 436 438 431 441 428 426 423 436 416 427 HOMO −4.96 −4.94 −4.66 −4.99 −4.68 −4.71 −4.65 −4.61 −4.56 −4.62 −4.59 (eV) LUMO −1.35 −1.57 −1.36 −1.51 −1.36 −1.44 −1.33 −1.30 −1.32 −1.38 −1.47 (eV)

(207) According to the test data in the table 1, the dibenzoheterocyclic compound provided by the invention has high thermal decomposition temperature and has higher thermal stability after film formation, material molecules are not easy to decompose or crystallize along with heat generated during the use of a device, the functions of a light-emitting layer can be kept stable, the breakdown of the device can be avoided, and the service life of the device can be prolonged. Meanwhile, the dibenzoheterocyclic compound has a low LUMO energy level (−1.30 to −1.57 eV), thereby being favorable for injecting and transporting electrons to the light-emitting layer and increasing the electron ratio. Because the hole transport performance of a semiconductor material is generally higher than the electron transport performance of the semiconductor material, the dibenzoheterocyclic compound is favorable for balancing electrons and holes, and the light-emitting efficiency of the device is improved.

(208) Test Case 2

(209) The properties, such as current, voltage, brightness and luminescent spectrum, of the organic light emitting diode provided by the embodiment 12 to the embodiment 19 and the contrast 1 are synchronously tested by adopting a PR 650 spectral scanning brightness meter and a Keithley K 2400 digital source meter system. Test results are as shown in table 2.

(210) TABLE-US-00002 TABLE 2 Dibenzo- Current Current heterocyclic Voltage/ density/ efficiency/ Chroma/ compound V mA/cm.sup.2 cd/A CIE (X, Y) Contrast 1 7.8 20 4.8 (0.15, 0.24) Embodiment 12 SP-01 4.7 20 17 (0.14, 0.23) Embodiment 13 SP-03 4.6 20 21 (0.15, 0.25) Embodiment 14 SP-04 4.5 20 21 (0.15, 0.25) Embodiment 15 SP-32 4.8 20 20 (0.16, 0.21) Embodiment 16 SP-34 4.5 20 18 (0.16, 0.28) Embodiment 17 SP-42 4.7 20 19 (0.15, 0.14) Embodiment 18 SP-55 4.6 20 20 (0.15, 0.12) Embodiment 19 SP-56 4.9 20 19 (0.15, 0.11)

(211) According to the table 2, as a light-emitting layer material, the dibenzoheterocyclic compound provided by the invention is favorable for lowering the driving voltages of the device and improving the light-emitting efficiency of the device, and a deep blue light-emitting device with high luminescence efficiency and stable performance can be obtained.

(212) Apparently, the above-described embodiments are merely examples provided for clarity of description, and are not intended to limit the implementations of the invention. Other variations or changes can be made by those skilled in the art based on the above description. The embodiments are not exhaustive herein. Obvious variations or changes derived therefrom also fall within the protection scope of the invention.