TW200909416A - Conjugated compound having hydroindoloacridine structure and application thereof - Google Patents

Abstract

The present invention discloses a conjugated compound having hydroindoloacridine structure and an application of taking it as the host material or the hole transport material in an organic electronic component. The general structure of the conjugated compound having hydroindoloacridine structure is shown in the following formula, wherein R1 to R5 can be the same or different atoms or functional groups.

Description

200909416 IX. DESCRIPTION OF THE INVENTION: TECHNICAL FIELD OF THE INVENTION The present invention relates to a compound compound, and more particularly to a conjugated compound having a hydrogenated indole structure and its use. [Prior Art] Phosphorescent metal complexes have recently been used as phosphorescent dopants for organic light-emitting diodes. Among these metal complexes used as the light-emitting layer in the organic light-emitting diode, the ring metallization of the base metal complex has caused the most extensive research due to the strong spin 'orbital coupling of the electronic configuration. Due to the spin-rail coupling, the single- and triple-excited states are mixed, thus shortening the lifetime of the triplet and increasing the phosphorescence efficiency. In addition, it has been found that the use of doping can improve the efficiency of the component, so the way of phosphorescent material is mixed in the host material, and the blue phosphorescent host material gradually becomes the focus of research. In the previous literature, blue was reported. Phosphorescent host materials are mainly carbazole, and the high-order triplet energy is suitable for use as a blue phosphorus: light host material. In view of this, the development of new organic compounds with high thermal stability and high triplet energy to extend the life of components and improve luminous efficiency is still a subject worthy of industrial attention. SUMMARY OF THE INVENTION In view of the above-described background of the invention, in order to meet the industrial requirements, the present invention provides a novel conjugated compound having a hydrogenated acridine structure and its use as a main illuminant in organic electronic device page 5, 200909416. Application of a host material, an electronic transport material, or a hole transport material. It is an object of the present invention to provide a highly thermally stable compound compound having a hydrogenated ruthenium acridine structure for improving the service life of an organic electronic component. Another object of the present invention is to provide a high triplet state. A common compound with a hydrogenated acridine structure to complement the existing energy levels that are generally not applicable to the blue phosphorescent main 35 material and common types of luminescent materials such as silver (8) (8) Red, blue, and green metal complex materials such as iron (〇s), according to which, in order to achieve economic benefits and industrial utilization. In accordance with the above objects, the present invention discloses a sister compound having ten chlorinated bite structures and its use as an organic material, an electron conductive material or a hole conducting material in an organic electronic component. Among them, the general structure of the above conjugated compound having a hydrogenated, bitten structure is as follows:

Wherein Ri~R may be the same or different atoms or substituent groups. Page 6 200909416 The present specification also discloses the use of the above ruthenium compound having a hydrogenated acridine structure, in particular, a main illuminant material, an electron conductive material, and an organic electroluminescent device and/or a phosphorescent device. A hole conducting material; or an electron conducting material or a hole conducting material applied to other organic electronic components. [Embodiment] The direction of the present invention as discussed herein is a conjugated compound having a hydrogenated acridine structure and its use. In order to thoroughly understand the present invention, detailed process steps or constituent structures will be presented in the following description. Obviously, the practice of the invention is not limited to the specific details that are apparent to those skilled in the art. On the other hand, well-known components or process steps are not described in detail to avoid unnecessarily limiting the invention. The preferred system of the present invention will be described in detail below, but the present invention may be widely practiced in other systems in addition to the detailed description, and the scope of the present invention is not limited thereto, and the scope of the following patents will prevail. The first embodiment of the present invention discloses a conjugated compound having a hydrogenated acridine structure, and the general structure of the above-mentioned compound having a hydrogenated bite structure is as follows:

Page 7 200909416 wherein W~R5 may be the same or different, and R1 to R5 are independently selected from one of the following groups: a hydrogen atom; a halogen-substituted aryl group; a C1-C20 haloalkyl-substituted aryl group; C1 -C20 haloalkyl substituted arylalkyl; aryl substituted C1-C20 alkyl; C1-C20 alkyl (eg methyl, ethyl, butyl, cyclohexyl, etc.); C1-C20 alkoxy (alkoxy group); an amino group; an amine group substituted with an aryl group; an amine group substituted with a C1-C20 alkyl group; a nitrile group; a nitro group; a carbonyl group ); cyano group (-CN); aromatic amine group having a substituent; phosphorus oxygen (P = 0) aromatic group; Si atom aromatic group; heterocyclic group. Here, the above R4 and R5 are not simultaneously a hydrogen atom. The aforementioned aromatic group includes phenyl, naphthyl, diphenyl, anthryl, pyrenyl, phenanthryl and dibenzopentacyclic ( Fluorene), or other forms of polyphenyl ring substituents. The aforementioned heterocyclic group may be pyrane, pyrroline, furan, benzofuran, thiophene, benzothiophene. , 0 to t pyridine, quinoline, isoquinoline, pyrazine, pyrimidine, pyrrole, pyrazole, pyrazole Imidazole, 0 indole, thiazole, isothiazole, oxazole, isoxazole, benzopyrene (benzothiazole), benzoxazole, benzoxazole, 1,2,4-trioxalate (1,2,4-triazole), 1,2,3-three-degree sputum (1,2,3 -triazole), 1, 2, 3, 4-tetras, tetraazole, with phenanthroline, or other forms of heteronuclear aromatic rings. 200909416 The structure of a preferred example of the conjugated compound having a hydrogenated acridine structure according to the present embodiment and the manner of formation thereof will be described below. However, the scope of the specification should be determined by the scope of the following patent. It should not be limited to the following examples.

Example 1 Method for forming a compound compound having a hydrogenated acridine structure First, compound F-01 (10 mmole), taste D (carbazole, 10 mmole), carbonic acid page 9 200909416 potassium (100 mmole) 'sodium sulfate (i〇〇mm〇ie) and copper powder (丨mm〇ie), placed in the reaction flask, added Jingji benzene (20 mL) 'heated at reflux temperature for 24 hours, after the reaction is completed, removed by vacuum distillation Nitrobenzene, the remaining mixture is extracted with water and di-methane, and the organic layer is collected. [Salting out water and concentrating to obtain compound F_〇2, as shown in Scheme 1.

F-01 F-02

Scheme 1

Next, the compound F-02 (10 mmole) was dissolved in a reaction flask using THF (50 mL), and a lithium reagent or a Grinna reagent (20 mmole) was added thereto, and the mixture was reacted for 18 hours under a nitrogen atmosphere. After the end of the reaction, the reaction was stopped by adding a saturated aqueous solution of ammonium sulfate, and extraction was carried out with ethyl acetate. After the organic layer was separated by water, the solvent was removed, and acetic acid (10 mL) and concentrated hydrochloric acid (1 mL) were added at reflux temperature. The reaction is shown as Scheme2. After the reaction, the acetic acid and hydrochloric acid are neutralized by a saturated aqueous solution of sodium carbonate. When the solution reaches a weak alkalinity, the solid is collected by suction filtration, and then recrystallized by using ethanol to obtain a conjugated compound having a hydrogenated acridine structure. .

a.) R-MgBr or RLi, THF, 18h__ b_) HCl(aq), HOAc, reflux, lh, two steps 52 % F-02

R R

Scheme 2 Page 10 200909416

Example 2 8.8-bis-(4-tert-butylbenzene)-8-hydrogen-, 嗓-[3,2,1-(1 acridine 8.8- Bis-(4-tert-butyl-phenyl)-8H- Indol〇P,2,l-de]acridine (hereinafter referred to as DPIA-®u)

DPIA-fiu NMR (400 M Hz, CDC13): ^ 1.23 (s, 18 H), 6.94 (d, /=8.4 Hz, 4 H), 7.04-7.08 (m, 3 H), 7.20 (d, > 8.4 Hz, 4 H), 7.29-7.38 (m, 3 H), 7.5 l (t, ^=8 Hz, 1 H), 7.91 (d, ^=7.6 Hz, 1H), 8.10 (t, /= 7.2 Hz, 3 H) 13C NMR (100 M Hz, CDC13): ^ 31.3 (CH3), 34.3 (C), 56.3 (C), 113.3 (CH), 114.4 (CH), 117.9 (CH), 121.0 (CH) , 121.1(CH), 121.8(C), 122.1(CH), 122.6(CH), 124.5(CH), 126.1(CH), 126.3(CH), 126.8(C), 127.3(CH), 128.3(C) , 129.7 (CH), 132.0 (CH), 132.5 (C), 136.9 (C), 137.6 (C), 138.6 (C), 143.3 (C), 149.0 (C). HRMS (El, m/z): Calcd for C39H37N 519.2926, found 519.2913 (M+) Anal. Calcd. for C39H37N: C, 90.13; H, 7.18; N, 2.70 %. Found: C, 89.98; H, 7.09 ; N,2·66 %. (DPIA_® u The UV absorption and spectroscopy spectra are shown in the first figure)

Example 3 8.8- bis-(4'-triphenyl oxabenzene-4-)-8-hydrogenated bud-[3,2,l-de]acridine 8.8- Bis-(4-triphenylsilanyl-phenyl)- 8H-indolo[3,2,l-de]acricline (hereinafter referred to as DPIA-BS) Page 11 200909416

!H NMR (600 μ Hz rn DPIA_BS 7.52-7.56 (m, 13 H), 7.96 (^^3⁄4 , I.〇5-7.13 (m, 8 H), 7'33-7.44 (m, 22 H), For C67H49NSi2: C, 87 06 ' hi:, also, 2 prints, 8.14 (t, household 8.0 take 4 H) · So Calcd. ' 5·34; N, i.52%. Found: c,86.68; H, 5.36; N, .° UV absorption and emission spectrum, see the second figure)

Example 4 8.8- bis-(4-bromophenyl)-8-hydrogenated 丨 321 but bite 8.8- BiS-(4-br_-Phenyl)_8H_ind〇1〇[321_de_^^

lU NMR (400 M Hz, CDC13): ^ 6.90 (d, ^8.0 Hz, 4 H), 6.97 (d, > 8.0 Hz, 1 H), 7.00 (d, ^=8.0 Hz, 1 H), 7.09 (t, >7.2 Hz, 1 H), 7.30-7.41 (m, 7 H), 7.53 (t, ^=8.0 Hz, 1H), 7.93 (d, ^8.0 Hz, 1 H), 8.07 (d, /=8.0 Hz, 1 H), 8.1 l(d, ^8.0 Hz, 2 H). , 3C NMR (100 M Hz, CDC13): 56.4(C), 110.0(C), 113.6(CH), 114.4( CH), 118.6(CH), 120.9(C), 121.2(CH), 121.4(CH), 122.1(C), 122.4(CH), 122.9(CH), 125.8(CHX 126.5(CH), 126.6(C) , 126.8(C), 127.9(CH), 131.0(CH, C), 131.5(CH), 131.8(CH), 136.8(C), 137.3(C), 138.6(C), 144.7(C) HRMS (El) , m/z): calcd for CsiHwBqN 562.9884 found 562.9888 (M ). Page 12 200909416

Example 5 8.8- bis-(4'-triphenyl-biphenyl-4-)-8-argon oxime-[3,2,l-de]acridine 8.8- Bis-(4,-triphenylsilanyl- Biphenyl-4-yl)-8H-indolo[3,2,1 -de]acridine (hereinafter referred to as DPIA-BSP)

!H NMR (400 M Hz, CDCls): ^ 7.12-7.22 (m, 7 H), 7.33-7.65 (m, 46 H), 7.97 (d, ^8.0 Hz, 1 H), 7.09 (t, ^ 7.2 Hz, 1 H), 8.11-8.19(m, 3 H). 13C NMR (100 M Hz, CDC13): 56.7(C), 113.5(CH), 114.5(CH), 118.3(CH), 121.2(CH) ), 121.3(CH), 122.1(C), 122.3(CH), 122.8(CH), 126.2(CH), 126.4(CH), 126.5(CH), 126.8(CH), 127.7(CH, C), 127.9 (CH), 128.0(C), 129.6(CH), 130.6(CH), 131.9(CH), 132.0(C), 133.0(C), 134.2(C), 136.4(CH), 136.8(CH), 137.0 (C), 137.6(C), 138.6(C), 138.9(C), 141.5(C), 145.5(C). HRMS (FAB, m/z): calcd for C79H57Si2N 1075.4030 found 1076.4111 (M++1) Anal. Calcd. for C79H57Si2N: C, 88.14; H, 5.34; N, 1.30 %· Found: C, 88.03; H, 5.21; N, 1.25 %. (See the third diagram for the ultraviolet absorption and luminescence spectrum of DPIA-BSP.) According to the present embodiment, the above conjugated compound having a hydrogenated acridine structure has good thermal stability and high triplet energy level difference. Etc. Therefore, when the above conjugated compound having a structure of hydrogenated acridine on page 13 200909416 is applied to an organic electronic component, in addition to high thermal stability, the life of the organic electronic component can be increased. When the conjugated compound of the pyridine structure is applied to the organic light-emitting element, it can further complement the existing energy level materials which are generally not applied to the main illuminant material, and various types of luminescent materials, such as silver (lr), The addition of a phosphorescent material of a metal complex such as (Pt) or iron (〇s) to adjust the light-emitting layers of various practically desired wavelengths. In the present embodiment, the above conjugated compound having a hydrogenated acridine structure can be used for an organic electroluminescence element and/or a phosphorescence element, particularly for an organic electroluminescence element. / or the host material in the phosphor element, or the hole transport material. Further, the above-mentioned compound compound having a hydrogenated acridine structure can also be applied to a hole transport material of other organic electronic devices. The above organic electronic component may be an organic light emitting device, an organic solar cell, an organic thin film transistor, an organic photoconductor, or other organic semiconductor device familiar to those skilled in the art. An organic light emitting element according to a second embodiment of the present invention is disclosed. In general, the color of the light emitted by the organic light-emitting element is mainly determined by the organic material having the fluorescent property in the element. Therefore, the organic light-emitting element can be mixed with a small amount of light-emitting efficiency in the main light-emitting body (guest). To improve the recombination efficiency of the two carriers, these guest emitters have a smaller energy gap than the main emitter, a higher luminous efficiency, and a shorter recombination lifetime than the main emitter. Therefore, the exciton of the main emitter is (excit〇n) Transfer to the guest illuminant by the process of energy transfer for rapid and efficient recombination. In addition to the efficiency of the illuminating light on page 14, 200909416, the color of the illuminating light can also span the entire visible light region. The guest emitter is often used in conjunction with the main illuminator in the form of co-evaporation (co_evap〇rati〇n) or dispersion (diSperSi〇n), with energy transfer or carder trap. The mode accepts the amount of the main illuminant bin b from being excited, resulting in the generation of different colors (re(j, green, biue) and enhancing the luminous efficiency of the element. In addition to the above-mentioned fluorescent material (Flu〇reseence) guest illuminant, The new development is the study of Phosphorus materials (Ph〇Sph〇rescence). When the organic molecules are excited, there will be /4 excited electrons forming asymmetrical spins of singlet 3 + 6) form, and released by crab light. The energy 'but 3/4 of the excited electrons will form a symmetrical spin triplet state 'and release energy with non-radioactive phosphorescence and greatly lose performance' and reduce luminous efficiency. At present, materials capable of emitting phosphoric light in the triplet state of excimer electrons are organometallic compounds, and the central metal is a transition metal such as: Os, Ir, Platinum (Pt), (Eu), ruthenium (Ru), etc. and its ligand is a nitrogen-containing heterocyclic compound. According to this embodiment, the above organic light-emitting element includes a pair of electrodes and at least one organic layer between the electrodes. Wherein at least one of the organic layers comprises a light-emitting layer, and at least one of the organic layers comprises a ruthenium compound having a hydrogenated acridine structure, and the general structure of the above-mentioned conjugated compound having a hydrogenated acridine structure As follows: Page 15 200909416 R2

One of the group: a hydrogen atom; a halogen-substituted aromatic group; a C1-C20 halogen-substituted aromatic group; a C1-C20 halogen-substituted aromatic alkyl group; an aromatic-substituted 匚1 _c2 fluorene group C1-C20 alkyl (for example: methyl, ethyl, butyl, cyclohexyl, etc.); ci_c2 alkoxy group; amino group; amine group substituted with an aryl group; C20 alkyl-substituted amine group; nitrile group; nitro group; carbonyl group; cyano group (-CN); aromatic amine group having a substituent; phosphorus oxygen P = 0) aromatic group; Si atom aromatic group; heterocyclic group. The aforementioned aromatic group includes phenyl, naphthyl, diphenyl, anthryl, pyrenyl, phenanthryl and di-p-pentacene ( Fluorene), or other forms of polyphenyl ring substituents. The aforementioned heterocyclic group may be α-pyrane, pyrroline, furan, benzofuran, 11 thiophene, benzoheptene ( Benzothiophene), pyridine, quinoline, isoquinoline, pyrazine, pyrimidine. Pyrol (pyrrole), efct^(pyraz〇le), feeding page 16 200909416 0 sitting (11111 (132〇16), 1* cited '1 flower (111<1〇16), sigh 11 sitting (111132〇16 ), 嗟 嗟 (18〇1:111 & 2〇16), 0ox 0 oxazole, isoxazole, benzothiazole, benzoxazole, l , 2,4-Si, (l,2,4-triazole), 1,2,3-St, (1,2,3-triazole) 1,2,3,4-tetraoxatetrazole With phenanthroline, or other forms of heteronuclear aromatic rings. In a preferred embodiment according to this embodiment, the above conjugated compound having a hydrogenated acridine structure may be applied to the above organic light-emitting element. In another preferred embodiment of the present embodiment, the conjugated compound having a hydrogenated acridine structure may be one of the host materials of the light-emitting layer applied to the above organic light-emitting element. The luminescent layer may further comprise a guest illuminant material, and the foregoing guest illuminant material comprises a transition metal complex. The transition metal complex may be one selected from the group consisting of铱 (Ir), platinum (Pt), 锇 (〇 s), copper (Cu), 铑 (Rh), 铕 (Eu), 钌 (Ru), etc. The above-mentioned guest illuminant material may be blue, green, A phosphorescent material of a red color, etc. In another preferred embodiment according to this embodiment, the above conjugated compound having a hydrogenated acridine I structure may be a hole conducting layer applied to the above organic light emitting device. In another preferred embodiment of the present embodiment, the conjugated compound having a hydrogenated acridine structure may be an electron-conducting layer applied to the organic light-emitting device. The general procedure for forming an organic light-emitting device is an ITO having an etched circuit pattern. Glass, add neutral detergent · deionized water = 1:50 cleaning solution, shake in a ultrasonic oscillator for 5 minutes, then brush the glass with a soft brush, then place the glass in 50 mL deionized The water and electronic grade acetone were shaken for 5 minutes, and finally dried with nitrogen 200909416. The cleaned IT glass was placed in the ultraviolet light _ ozone machine, the time slave was 5 minutes, and the mosquito was taken out on the substrate (ΙΤ〇_下) Put the tester down and vacuum until The degree of vacuum of the body reaches - the step of evaporation can be carried out. The condition of the test is that the rate of the organic mineral film is controlled between 12 A / s 'the desired organic film is sequentially steamed, while the metal surface, magnesium The metal film thickness of the silver co-evaporation is 5 A/s for the rate town, 0.5 A/s for the silver, and the town: silver = 1 〇 55 nm. Finally, the silver of the upper layer 1 () 〇 coffee is used as a protective layer. If the metal is selected to be a gasification fiber system, the vaporization clock must first be vaporized at a rate of Oj A/s, the film thickness of which is controlled to i legs, followed by a layer of 100 nm aluminum as a protective layer. During the coating, the rotation rate of the component is 20 rpm. After the transpiration beam, it is necessary to wait for 20 minutes for the metal electrode to cool down before returning the cavity to the normal pressure. On the other hand, after the preparation of the OLED element is completed, the electro-spectral fluorescence spectrum (EL spectra) and the αΕ coordinate map (CIE coordination) of the measuring element are measured by the Hitach F_45〇〇spectra scan spectrometer, and 'by Keithley 24〇〇 Pr〇grammable voltage-current source measures the current (current), voltage (v〇ltage) and brightness (brightness) of a component. All of the above measuring instruments are operated at room temperature (about 20 ° C) under atmospheric pressure.

Example 12, by using the above-mentioned general procedure for forming an organic light-emitting element, using DPIA-u, DPIA-BS, DPIA-Br, and DPIA-BSP as the main illuminant materials, respectively doping blue light-breaking materials to form OLED elements, The aforementioned doped blue phosphorescent material is as follows: Page 18 200909416

The individual components of the above components are structured as follows: Component A: NPB (30 nm) / DPIA-®u: 6 % FIrpytz (30 nm) / BCP (10 nm) / Alq (30 nm). Component B: TCTA (30 nm) /DPIA-Bu: 6 % FIrpytz (30 nm) / BCP (10 nm) / Alq (30 nm). Component C: TCTA (30 nm) / DPIA-BS: 6 % FIrpytz (30 nm) / BCP (10 nm ) / Alq (30 nm) The optical properties and efficiency measurement results of the above elements A to C are shown in Table 1 below. Table 1: Component startup voltage (V) Maximum external quantum efficiency (%, V) Brightness (at 100 mA/m2) (cd/m2) Current efficiency (cd/A, V) Maximum efficiency (lm/W, V) CIE Coordinates (x, y) at 10V ABC 3.9 5.9 4.8 7.45, 6.5 7.76, 9.5 2.04, 9.0 5930, 10.4 6171, 13.1 2099, 11.9 12.53.6.5 13.45.9.5 3.67, 9.0 6.06, 6.5 4.52, 9.0 1.28, 9.0 0.15, 0.24 0.15, 0.25 0.19, 0.29 From the table - Lin Ke; t aj to this specification of the co-consumption compound with hydrogen oxime π 丫 bite structure can be used as Wei main riding material, and the organic light-emitting two shop. Referring to the above table i, the figure shows that the above-mentioned elements A to c can emit blue scale light, and the above-mentioned elements A to c have high luminance, high current efficiency, and excellent α Ε coordinates. In the present embodiment, 'the above-mentioned compound having a hydrogenation, a bite-biting structure can be used for the main illuminant material (h〇St material) used in an organic luminescence element on page 19 200909416 or a hole. Conductive material (h〇le transp〇rt coffee (4)). On the other hand, the above conjugated compound having a hydrogenated acridine structure has a property of hole conduction so that Φ can be applied to an organic light-emitting element or even a hole-conducting material of other organic electronic elements. According to the present specification t ′, since the above-mentioned conjugated compound having a hydrogenation structure has a souther thermal stability, the above-mentioned hydrogenated ruthenium structure is used.

When the co-consumed compound should be left with the organic electronic component towel, the service life of the organic electronic component can be effectively extended. m. Because the above-mentioned compound having the hydrogenation residual structure has a high triple test of the county, therefore, the above-mentioned money is When the co-ablative structure of the Yu-Bian structure should be secretive to the organic light-emitting element, it can be further complemented by the energy level difference that can not be achieved in the current blue-filled main riding material, and the general-purpose various types of materials ), materials such as bismuth, iron (four) and other metal complexes, in order to achieve economic benefits and industrial use. Obviously, the invention may have many modifications and differences in accordance with the description of the shackles in the above system. It is therefore necessary to understand within the scope of the appended claims and claims, and the invention may be practiced in other systems in addition to the detailed description above. The above is only the preferred system of the present invention and is not intended to limit the scope of the invention; any equivalent changes or modifications made without departing from the spirit of the invention should be included in the following. Please refer to the patent scope. Page 20 200909416 [Simple description of the diagram] The first picture is the UVA absorption and emission spectrum of DPIA-U-U; the second picture is the UV absorption and emission spectrum of DPIA_BS; The third picture is DPIA-BSP Ultraviolet light absorption and luminescence spectra; and • The fourth diagram is a luminescence spectrum of component A to component C formed according to the present specification. « [Main component symbol description]

Page 21

Claims (1)

200909416 X. The scope of application for patents: 1. A kind of hydrogenated bow. A common roll compound of the bite structure, which has hydrogenation. The general structure of the compound compound of the biting structure is as follows: R2 Wherein R1 to R5 may be the same or different, and R1 to R5 are independently selected from one of the following groups: a ruthenium atom, a halogen-substituted aryl group, a C1-C20 haloalkyl-substituted aryl group, a C1-C20 halane. Alkyl-substituted arylalkyl group, aryl-substituted C1-C20 alkyl group, C1-C20 alkyl group, C1-C20 alkoxy group, amino group, aryl-substituted amine group, having C1-C20 Alkyl-substituted amine group, nitrile group, nitro group, carbonyl group, cyano group (_CN), substituted aromatic amine group, phosphorus oxide (P = 0) an aromatic group, an aromatic atom of a Si atom, a heterocyclic group; wherein R4 and R5 are not a hydrogen atom at the same time. 2. The conjugated compound having a hydrogenated acridine structure according to the above-mentioned claim, wherein the above-mentioned aryl group comprises one of the following groups: phenyl, naphthyl, and stupid. Diphenyl, anthryl 'benzopyranyl' page 22 200909416 (pyrenyl), phenanthryl and dibenzo pentene or other forms of polyphenyl ring substituents. 3. The conjugated compound having a hydrogenated acridine structure according to claim 1, wherein the heterocyclic group comprises one of the following groups: pyrane, pyrroline (pyrroline) ), furan, benzofuran, thiophene, benzothiophene, pyridine, quinoline, isoquinoline, pyrazine , pyrimidine, pyrrole, pyrazole, imidazole, indole, thiazole, isothiazole, ° evil ° oxazole, isoxazole, benzothiazole, benzoxazole, 1,2,4-trioxol (l,2,4-triazole) , 1,2,3-three ^^(lJJ-triazole), 1,2,3,4-tetrazoic (1,2,3,4-tetraazole), with phenanthroline, or Other forms of heteronuclear aromatic rings. 4. The conjugated compound having a hydrogenated acridine structure as described in claim 1, wherein the conjugated compound having the acridine structure described above is applied to an organic electroluminescence element and / or phosphorescence components. 5. The conjugated compound having a hydrogenated acridine structure as described in claim 1, wherein the conjugated compound having a hydrogenated acridine structure is applied to an organic electroluminescent device and/or phosphorescent The main illuminant material in the element (host page 23 200909416 material) 0. The conjugated compound having a hydrogenated acridine structure as described in claim 1, wherein the above has a hydrogenated acridine structure The conjugated compound is applied to a hole conducting material in an organic electronic component. 7. An organic light-emitting device comprising a pair of electrodes and at least one organic layer between the electrodes' wherein the at least one organic layer comprises a light-emitting layer, and at least one of the organic layers comprises a hydrogenated germanium A common compound of the acridine structure, the general structure of the compound compound having a hydrogenated bite structure is as follows: R2 One of the groups: a hydrogen atom, a halogen-substituted aryl group, a C1-C20 haloalkyl-substituted aryl group, a C1-C20 haloalkyl-substituted arylalkyl group, an aryl-substituted C1-C20 alkyl group, C1 -C20 alkyl, C1-C20 alkoxy, amino group, aryl-substituted amine group, C1-C20 alkyl-substituted amine group, nitrile group, sulfhydryl group Group), carbonyl group, cyano group (-CN), aromatic amine group with substituent, dish oxygen (P=0) Page 24 200909416 aromatic group, si atom aromatic group, heterocyclic ring a group; wherein R4 and R5 are not a hydrogen atom at the same time. 8. The organic light-emitting device according to claim 7, wherein the above aromatic group comprises one of the following groups: phenyl, naphthyl, diPhenyl, fluorenyl. (anthryl), pyrenyl, phenanthryl and benzophenone or other forms of polyphenyl ring substituents. 9. The organic light-emitting device of claim 7, wherein the heterocyclic group comprises one of the following groups: pyrane, pyrroline, 0f0i^ (furan), benzofuran, thiophene, benzothiophene, pyridine, quinoline, isoquinoline, 〇比口秦(pyrazine), pypyrimidine, n pyrrole, pyrazole, imidazole, indole, thiazole, and sigh. Isothiazole, oxazole, isoxazole, benzothiazole, benzoxazole, 1.2.4-trioxazole (l, 2, 4-triazole), 1,2,3-triazole (l,2,3-triazole), 1.2.3.4-tetrazolidine (l,2,3,4-tetraazole), with phenanthroline ), or other forms of heteronuclear aromatic rings. 10. The organic light-emitting device according to claim 7, wherein the above-mentioned conjugated compound having a hydrogenated acridine structure is applied to the light-emitting layer of the organic light-emitting element. The organic light-emitting device according to claim 7, wherein the conjugated compound having a hydrogenated acridine structure is a main illuminant material of the light-emitting layer of the organic light-emitting device. 12. The organic light-emitting device according to claim 7, wherein the above-mentioned co-consumed compound having a hydrogenated acridine structure is applied to an electron conductive material of the organic light-emitting element. 13. The organic light-emitting device according to claim 7, wherein the conjugated compound having the { 1 hydrogenated acridine structure described above is applied to the hole-conducting material of the organic light-emitting element. 14. The organic light-emitting device of claim 7, wherein the light-emitting layer comprises a guest light-emitting material, and the guest light-emitting material comprises a transition metal complex. 15. The organic light-emitting device according to claim 14, wherein the transition metal of the transition metal complex is selected from one of the following groups: iridium (Ir), platinum (Pt), .V^ (Os), copper (Cu), rhodium (Rh), europium (Eu), rhodium (Ru). 16. The organic light-emitting device of claim 14, wherein the guest emitter material is a blue phosphorescent material. The organic light-emitting device of claim 14, wherein the guest light-emitting material is a green phosphorescent material. 18. The organic light-emitting device of claim 14, wherein the guest emitter material is a red phosphorescent material. Page 26