CN110357784A - Organic electric-excitation luminescent compound and organic electroluminescent element - Google Patents

Organic electric-excitation luminescent compound and organic electroluminescent element Download PDF

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CN110357784A
CN110357784A CN201810351011.2A CN201810351011A CN110357784A CN 110357784 A CN110357784 A CN 110357784A CN 201810351011 A CN201810351011 A CN 201810351011A CN 110357784 A CN110357784 A CN 110357784A
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辛孟鸿
陈裕宏
林进志
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Xingchen Photoelectric Co ltd
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Xingchen Photoelectric Co ltd
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Abstract

The present invention provides a kind of organic electric-excitation luminescent compound, is indicated by structure formula (I) or structure formula (II), and wherein R is aromatic radical or heteroaryl perfume base.Structure formula (I) or structure formula (II) can be used to make organic electroluminescent element, improve the glass transition temperature of organic material layer whereby, and improve the luminous efficiency and thermal stability of light-emitting component.The present invention separately discloses a kind of organic electroluminescent element as made by aforementioned organic electric-excitation luminescent compound.Structure formula (I) andStructure formula (II).

Description

Organic electric-excitation luminescent compound and organic electroluminescent element
Technical field
The invention relates to a kind of organic electric-excitation luminescent compound and applied organic electroluminescent elements, especially It is about a kind of organic electroluminescent element with high glass transition and applied organic electroluminescent element.
Background technique
Electroluminescence (Electroluminescence；EL) refer to when electric current passes through substance or substance is under strong electrical field Luminous phenomenon is sometimes referred to as cold light in consumer goods production.The research direction of electroluminescence is mainly organic material at present Application.Such as using electroluminescence characteristic Organic Light Emitting Diode (Organic Light-Emitting Diode, OLED), refer to that organic semiconducting materials and luminescent material reach the technology for shining and realizing display under electric current driving.It compares In liquid crystal display (liquid crsystal display, LCD), OLED is applied to organic hair made by display panel There are many advantages for optical display unit, such as have ultralight, ultra-thin (OLED thickness can be lower than 1mm), brightness height, visible angle big (reachable 170 degree), do not need backlight, low in energy consumption, fast response time, clarity are high, calorific value is low, anti-seismic performance is excellent, manufacturing cost It is low and flexible etc..However, EL part leans on itself light source because of no backlight, therefore its luminous efficiency and the aobvious weight of service life benefit It wants, and is that current technology development wants to improve the emphasis broken through.
No. 7714145 materials disclosed for organic electroluminescent element of U.S. Patent No., and it is right with 2,2 '-to disclose it Claim material of the two fluorenyl structural compounds of substituent group diamine -9,9 '-spiral shell as organic illuminating element；German Patent No. No. 102010045405 compounds then disclosed for electroluminescent organic material, wherein disclosed compound has 9, 9 '-spiral shell, two fluorene group, manufactured organic electroluminescent device have longer service life relative to product before (lifetime), this Patent Case points out previous luminescent material because of lower glass transition temperature (glass transition
Temperature, Tg) and cause thermal stability bad.
In the processing procedure of organic electroluminescent device, after organic electric-excitation luminescent compound is coated to electrode in the form of a film, Follow-up process, such as High-temperature Packaging are also faced, may result in the degradation of organic electric-excitation luminescent compound.Therefore, if there is When electroluminescent compound can have a higher glass transition temperature there will be better thermal stability to prevent High-temperature Packaging or Product using when generated high fever cause the short life of organic electroluminescent element.Therefore, in order to ensure organic electric-excitation luminescent The service life of compound and organic electroluminescent element needs the Organic Electricity that exploitation has high-luminous-efficiency and high glass transition temperature Excite luminescent material.
Summary of the invention
The present invention provides a kind of organic electric-excitation luminescent compound, has such as rectangular structure formula (I) or structure formula (II) institute The structure shown:
Wherein, R is aromatic radical or heteroaryl perfume base.
Preferably, R in structure formula (I) or structure formula (II) be selected from by aromatic radical, heteroaryl perfume base,
Composed group Group,
Wherein X and X ' can respectively be stood alone asY can be
Wherein, R1Selected from by hydrogen, the alkyl that is substituted or is unsubstituted, cyano, the aromatic radical for being substituted or being unsubstituted, Group composed by the heteroaryl perfume base and mutually parallel aromatic radical or heteroaryl perfume base for being substituted or being unsubstituted；
R2System selected from by hydrogen, the alkyl that is substituted or is unsubstituted, cyano, the aromatic radical for being substituted or being unsubstituted, warp Replace or the heteroaryl perfume base that is unsubstituted and mutually group composed by the aromatic radical or heteroaryl perfume base of a pair of horses going side by side；
R3System selected from by hydrogen, the alkyl that is substituted or is unsubstituted, cyano, the aromatic radical for being substituted or being unsubstituted, warp Replace or the heteroaryl perfume base that is unsubstituted and mutually group composed by the aromatic radical or heteroaryl perfume base of a pair of horses going side by side；
R4System selected from by hydrogen, the alkyl that is substituted or is unsubstituted, cyano, the aromatic radical for being substituted or being unsubstituted, warp Replace or the heteroaryl perfume base that is unsubstituted and mutually group composed by the aromatic radical or heteroaryl perfume base of a pair of horses going side by side；
R5System is selected from the alkyl, cyano, the aromatic radical for being substituted or being unsubstituted, Yi Jijing by being substituted or being unsubstituted Replace or the heteroaryl perfume base that is unsubstituted composed by group；And
R6With R7System is each independently selected from alkyl, cyano, the fragrance for being substituted or being unsubstituted by being substituted or being unsubstituted Group composed by base and the heteroaryl perfume base for being substituted or being unsubstituted.
According to the present invention, the compound of aforementioned structure formula (I) or structure formula (II) may include such as the compound of flowering structure One or more of them:
But the present invention has structure formula (I) or the organic electric-excitation luminescent compound of structure formula (II) is not limited with above-mentioned.
In the 2 of the present invention, 2 '-aromatic series diamine base -9, during 9 '-spiral shells two are fluorene structured, be with
9,9 '-spiral shell, two fluorene group is separately connected identical amido on two fluorenyls, to form symmetrical structure as skeleton.This Outside, the wherein substituent group in amido is hexichol fluorenes, and the citing of another substituent group is such as aforementioned.It organic is electrically excited due to of the invention Optical compounds have structure as above, therefore its glass transition temperature (Tg) with higher, are for example, greater than or equal to 175 ℃。
The present invention separately provides a kind of organic electroluminescent element, including anode, electric hole implanted layer, electric hole transport layer, shines Layer, electron transfer layer, electron injecting layer and cathode sequentially storehouse, wherein the electric hole implanted layer, the electric hole transport layer, described At least one of which of luminescent layer, the electron transfer layer and the electron injecting layer includes organic electric-excitation luminescent as described above Compound.
Detailed description of the invention
Fig. 1 show the diagrammatic cross-section of the organic electroluminescent element of specific example of the present invention.
[symbol description]
10 anodes
20 electric hole implanted layers
30 electric hole transport layers
30a the first electric hole transport layer
30b the second electric hole transport layer
40 luminescent layers
50 electron transfer layers
60 electron injecting layers
70 cathodes
80 substrates
100 organic electroluminescent elements
Specific embodiment
In order to enable the usual skill in this field to understand and implement the present invention, it will hereafter cooperate attached drawing, this hair is described in detail Bright organic electric-excitation luminescent compound and applied organic electroluminescent element.It is noted that protection scope of the present invention When being subject to patent application the scope of the patents institute defender, rather than it is limited with the embodiment for being exposed in hereafter.Therefore, without prejudice to originally Under the spirit of invention and the situation of range, when can make change and modify to following embodiments.In addition, in order to it is succinct with it is clear For the sake of, the known structure in part and process details will not be exposed in hereinafter.It is noted that schema is to illustrate for mesh , do not drawn completely in accordance with full size.
The present invention provides a kind of organic electric-excitation luminescent compounds, and it includes 2,2 '-aromatic series diamine base -9,9 '-spiral shells two It is fluorene structured, that is, there is the structure such as rectangular structure formula (I) or structure formula (II):
Wherein, R is aromatic radical or heteroaryl perfume base.
In some specific examples, R in structure formula (I) or structure formula (II) be selected from by aromatic radical, heteroaryl perfume base, Composed group Group,
Wherein X and X ' can respectively be stood alone asY can be
R1System selected from by hydrogen, the alkyl that is substituted or is unsubstituted, cyano, the aromatic radical for being substituted or being unsubstituted, warp Replace or the heteroaryl perfume base that is unsubstituted and mutually group composed by the aromatic radical or heteroaryl perfume base of a pair of horses going side by side；
R2System selected from by hydrogen, the alkyl that is substituted or is unsubstituted, cyano, the aromatic radical for being substituted or being unsubstituted, warp Replace or the heteroaryl perfume base that is unsubstituted and mutually group composed by the aromatic radical or heteroaryl perfume base of a pair of horses going side by side；
R3System selected from by hydrogen, the alkyl that is substituted or is unsubstituted, cyano, the aromatic radical for being substituted or being unsubstituted, warp Replace or the heteroaryl perfume base that is unsubstituted and mutually group composed by the aromatic radical or heteroaryl perfume base of a pair of horses going side by side；
R4System selected from by hydrogen, the alkyl that is substituted or is unsubstituted, cyano, the aromatic radical for being substituted or being unsubstituted, warp Replace or the heteroaryl perfume base that is unsubstituted and mutually group composed by the aromatic radical or heteroaryl perfume base of a pair of horses going side by side；
R5System is selected from the alkyl, cyano, the aromatic radical for being substituted or being unsubstituted, Yi Jijing by being substituted or being unsubstituted Replace or the heteroaryl perfume base that is unsubstituted composed by group；And
R6With R7System is each independently selected from alkyl, cyano, the fragrance for being substituted or being unsubstituted by being substituted or being unsubstituted Group composed by base and the heteroaryl perfume base for being substituted or being unsubstituted.
Wherein, organic electric-excitation luminescent compound of the present invention may include (but being not limited to) such as aforesaid compound (1) to compound (23)。
A specific example of the invention separately provides a kind of organic electroluminescent element.Referring to FIG. 1, Fig. 1 show this hair The diagrammatic cross-section of the organic electroluminescent element of bright specific example.Organic electroluminescent element 100 includes anode 10, electric hole note Enter layer 20, electric hole transmitting layer 30, luminescent layer 40, electron transfer layer 50, electron injecting layer 60 and cathode 70 sequentially storehouse, such as can It is set to 80 surface of substrate.Electric hole transmitting layer 30 also may include the first electric hole transmitting layer 3 0a and the second electric hole transmitting layer 3 0b.Its In, electric hole implanted layer 20, the first electric hole transmitting layer 3 0a, the second electric hole transmitting layer 3 0b, luminescent layer 40, electron transfer layer 50, electricity At least one of them of sub- implanted layer 60 includes organic material layer, and at least one of which of these film layers includes structure above (I) or the organic electric-excitation luminescent compound of structure formula (II), make organic electroluminescent element 100 that there is high shine to reach whereby Efficiency and high glass transition temperature.It in the present embodiment, is to make electric hole implanted layer 20, the first electric hole transmitting layer 3 0a, the second electric hole At least one of which of transmitting layer 3 0b includes the organic electric-excitation luminescent compound of above structure formula (I) or structure formula (II), such as Comprising compound (1) to the one of which of compound (23), but not limited to this.Wherein, the present embodiment is with the first electric hole biography At least one of which of defeated layer 30a and the second electric hole transmitting layer 3 0b include the Organic Electricity of above structure formula (I) or structure formula (II) For exciting optical compounds, but not limited to this.For example, in some embodiments, the first electric hole transmitting layer 3 0a and the second electric hole Transmitting layer 3 0b includes having for above structure formula (I) or structure formula (II) (or compound (1) to compound (23)) each independently Electroluminescent compound.In addition, the anode 10 of organic electroluminescent element 100 of the present invention is electrically coupleable to be set to substrate 80 The switch element on surface, such as thin film transistor (TFT), and cathode 70 is electrically coupleable to share voltage, but not limited to this.At other In specific example, anode 10, electric hole implanted layer 20, electric hole transmitting layer 30, luminescent layer 40, electron transfer layer 50, electron injecting layer 60 and cathode 70 stacking order can with Fig. 1 on the contrary, or so that cathode 70 is electrically connected to switch element, and anode 10 It is electrically connected to share voltage.Since the organic material layer of organic electroluminescent element 100 of the invention includes 2,2 '-virtue above-mentioned Fragrant race's diamine base -9,9 '-spiral shells two are fluorene structured, therefore its luminous efficiency is greater than or equal to 7.5cd/A, and organic electric shock of the invention The glass transition temperature (Tg) of organic electric-excitation luminescent compound in light-emitting component 100 is greater than or equal to 175 DEG C.
Illustrate production method and the spy of organic electroluminescent element object of the present invention by embodiment and comparative example below Property, with the technical characteristic that the present invention is furture elucidated.
Embodiment 1:
Firstly, providing substrate.Then conductive layer is formed in substrate, for example, includes tin indium oxide (Indium Tin Oxide, ITO) transparency conducting layer.Before substrate loads deposition system, first gone forward side by side with solvent, ultraviolet light or ozone clean substrate Row degreasing.Later, make transparency conducting layer above-mentioned as the anode of organic electroluminescent element, be sent to vacuum deposition chamber, then Deposition manufacture process or film-plating process are carried out in the top of substrate to make other film layers.Such as it is held in the palm with the vapor deposition boat of heating in about 10-6 (Torr) sequentially formed under vacuum degree environment electric hole implanted layer, the first electric hole transport layer, the second electo-kinetic transport layer, luminescent layer, Electron transfer layer, electron injecting layer and cathode.Wherein, the material of each film layer is as follows:
1. anode: tin indium oxide (Indium Tin Oxide, ITO).
2. electric hole implanted layer: NDP9, trade name are purchased from Novaled company.
3. the first electric hole transport layer: 2,2 '-aromatic series diamine base -9,9 '-spiral shell, two fluorenes include compound (1).
4. the second electric hole transport layer: HT2, structural formula are as follows:
5. luminescent layer: being all trade name comprising BH, BD and the BH doped with BD, be purchased from Chu Guangxingchan company, Japan.
6. electron transfer layer: it is public to go out the emerging production of light purchased from Japan comprising being trade name doped with quinoline lithium (Liq), ET by ET Department.
7. electron injecting layer: lithium fluoride (LiF)
8. cathode: including metallic aluminium (Al).
Embodiment 2 is to embodiment 9:
Embodiment 2 to embodiment 9 organic electroluminescent element production method and embodiment 1 production method substantially phase Together, only material used in the first electric hole transport layer is different, wherein the first electric hole transport layer of embodiment 2 to embodiment 9 Material sequentially separately include compound (2), compound (4), compound (5), compound (6), compound (9), compound (12), Compound (18) and compound (21), the material of other film layers are all same as Example 1.
Embodiment 10:
The production method of the organic electroluminescent element of embodiment 10 is roughly the same with the production method of embodiment 1, the two Do not exist together and be only that the first electric hole transport layer of embodiment 10 and material that the second electric hole transport layer uses is different from embodiment 1, wherein the first electric hole transport layer of embodiment 10 has the compound of following HT1 structure, and before the second electric hole transport layer includes State compound (12).
Comparative example:
The production method of the organic electroluminescent element of comparative example is roughly the same with the production method of embodiment 1, and the two is not The material for the first electric hole transport layer for being only that comparative example that exists together is the compound with HT1 structure, and the second electric hole transport layer Material be the compound with HT2 structure.
The embodiment of the present invention and the specificity analysis project of comparative example include the test of glass transition temperature and luminous efficiency. After forming organic electroluminescent element according to embodiment 1 to embodiment 10 and the production method of comparative example, at 1000 nits (nit) Brightness under, carry out the measurement of glass transition temperature and luminous efficiency respectively.Wherein, the measurement of glass transition temperature is to utilize Differential scans measurement method and carries out.The measurement of luminous efficiency is to utilize brightness photometer (model PR-655, by Photo Research public affairs Manufactured by department) it carries out.
The specificity analysis list of 1 embodiment of the present invention of table and comparative example
As shown in Table 1, the glass of the embodiment of the present invention 1 to the material used in the first electric hole transport layer of embodiment 9 turns It changes temperature (Tg) and is all greater than 137 DEG C, that is, be greater than the glass transition temperature of HT1 material corresponding to comparative example.In addition, this hair The glass transition temperature (Tg) of bright embodiment 10 material used in the second electric hole transport layer is 207 DEG C, also greater than implementation The glass transition temperature of the HT2 material corresponding into embodiment 9 and comparative example of example 1.Therefore, the structure formula (I) of the present invention Or structure formula (II) compound and provide preferable glass conversion temperature really as the organic electroluminescent element prepared by it Degree and thermal stability.
In addition, the compound that the compound (4) that uses of the compound (2) that embodiment 2 uses, embodiment 3, embodiment use (5), the maximum luminous efficiency for the compound (21) that embodiment 9 uses be respectively 11.0Cd/A, 10.8Cd/A, 9.3Cd/A and 10.1Cd/A is all higher than the 9.0Cd/A of Comparative Example H T1 material, therefore the present invention has having for structure formula (I) or structure formula (II) Electroluminescent compound has good luminous efficiency, it might even be possible to have compared to HT1 used in comparative example and HT2 material Better luminous efficiency.
In conclusion the present invention includes 2,2 '-aromatic series diamine base -9 of structure formula (I) and structure formula (II), 9 '-spiral shells two The organic electric-excitation luminescent compound of fluorenes has preferable glass transition temperature, and first using the organic electric-excitation luminescent made by it Part can combine the characteristic with preferable luminous efficiency, preferable thermal stability and preferable glass transition temperature.
The foregoing is merely presently preferred embodiments of the present invention, all equivalent changes done according to scope of the present invention patent with repair Decorations, are all covered by the present invention.

Claims (8)

1. a kind of organic electric-excitation luminescent compound, which is characterized in that have as shown in rectangular structure formula (I) or structure formula (II) Structure:
Wherein, R is aromatic radical or heteroaryl perfume base.
2. organic electric-excitation luminescent compound as described in claim 1, which is characterized in that the knot of the organic electric-excitation luminescent compound R in structure formula (I) and structure formula (II) be selected from by Composed group,
Wherein X and X ' can respectively be stood alone asY can be
Wherein R1System selected from by hydrogen, the alkyl that is substituted or is unsubstituted, cyano, the aromatic radical for being substituted or being unsubstituted, through taking Group composed by generation or the heteroaryl perfume base being unsubstituted and the mutually aromatic radical or heteroaryl perfume base of a pair of horses going side by side；
R2System selected from by hydrogen, the alkyl that is substituted or is unsubstituted, cyano, the aromatic radical for being substituted or being unsubstituted, be substituted or Group composed by the heteroaryl perfume base and mutually parallel aromatic radical or heteroaryl perfume base being unsubstituted；
R3System selected from by hydrogen, the alkyl that is substituted or is unsubstituted, cyano, the aromatic radical for being substituted or being unsubstituted, be substituted or Group composed by the heteroaryl perfume base and mutually parallel aromatic radical or heteroaryl perfume base being unsubstituted；
R4System selected from by hydrogen, the alkyl that is substituted or is unsubstituted, cyano, the aromatic radical for being substituted or being unsubstituted, be substituted or Group composed by the heteroaryl perfume base and mutually parallel aromatic radical or heteroaryl perfume base being unsubstituted；
R5System selected from by being substituted or being unsubstituted alkyl, cyano, the aromatic radical for being substituted or being unsubstituted and be substituted Or group composed by the heteroaryl perfume base being unsubstituted；And
R6With R7System is each independently selected from alkyl, cyano, the aromatic radical for being substituted or being unsubstituted by being substituted or being unsubstituted And group composed by the heteroaryl perfume base for being substituted or being unsubstituted, wherein R6With R7The atom being connect with it is collectively formed Fluorenyl.
3. organic electric-excitation luminescent compound as described in claim 1, which is characterized in that the organic electric-excitation luminescent compound includes At least one of them of following compound:
4. organic electric-excitation luminescent compound as described in claim 1, which is characterized in that the glass of the organic electric-excitation luminescent compound Glass inversion temperature is greater than or equal to 175 DEG C.
5. a kind of organic electroluminescent element, which is characterized in that comprising anode, electric hole implanted layer, electric hole transport layer, luminescent layer, Electron transfer layer, electron injecting layer and cathode sequentially storehouse, wherein the electric hole implanted layer, the electric hole transport layer, the luminescent layer, should At least one of which of electron transfer layer and the electron injecting layer includes organic to be electrically excited as claims 1 to 4 are described in any item Optical compounds.
6. organic electroluminescent element as claimed in claim 5, which is characterized in that the electric hole transport layer is passed comprising the first electric hole Defeated layer and the second electric hole transport layer, and the first electric hole transport layer and the second electric hole transport layer include not exactly the same material Material.
7. organic electroluminescent element as claimed in claim 6, which is characterized in that the first electric hole transport layer and second electricity Hole transport layer separately includes the organic electric-excitation luminescent compound.
8. organic electroluminescent element as claimed in claim 5, which is characterized in that the luminous effect of the organic electroluminescent element Rate is greater than or equal to 7.5cd/A.
CN201810351011.2A 2018-03-26 2018-04-18 Organic electric-excitation luminescent compound and organic electroluminescent element Pending CN110357784A (en)

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