CN104926805B - Electroluminescent organic material and device - Google Patents
Electroluminescent organic material and device Download PDFInfo
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- CN104926805B CN104926805B CN201510119396.6A CN201510119396A CN104926805B CN 104926805 B CN104926805 B CN 104926805B CN 201510119396 A CN201510119396 A CN 201510119396A CN 104926805 B CN104926805 B CN 104926805B
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Abstract
The present invention discloses a kind of compound, the structure with Formulas I, A-L-B-M-D.In the structure of the Formulas I: A is selected fromWith；L is linking group selected from the following: singly-bound, aryl, heteroaryl and a combination thereof, and can be further substituted；L-B-M has a structure that；M is selected from aryl, heteroaryl and a combination thereof, and can further be substituted；D has a structure that；X is O, S, Se or CR'R "；X1‑X8、Y1‑Y12、Z1、Z3‑Z8And Z11‑Z18It is N or CR each independently；Each R, R' and R " are selected from diversified substituent group；Wherein adjacent R substituent group can form fused rings；And R' and R " can form ring.Also composite and device of the description including the compound of formula I, such as OLED.
Description
Cross reference to related applications
The application is that the U.S. Provisional Patent Application submitted on March 18th, 2014 is required according to 35 U.S.C. § 119 (e)
The non-provisional application of 61/954th, No. 631 priority, the full content of the patent application are herein incorporated by reference this
Wen Zhong.
The each side of joint study agreement
The required present invention is one or more of the following each side by reaching Associated Univ's research agreement, with
It the name of one or more of lower each side and/or is made in conjunction with one or more of following each side: The Regents of the Univ. of Michigan,
Princeton University, University of Southern California and global silver-colored electrically (Universal Display Corporation).The association
It discusses the date of the invention required by making just to come into force with before, and the required present invention is because in the agreement
In the range of the activity that carries out and make.
Technical field
The present invention relates to the compounds for the main body being suitable in Organic Light Emitting Diode, and including its composite and dress
It sets.
Background technique
For several reasons, it is become more and more popular using the optical electron device of organic material.To manufacture in this way
Device material in many materials it is relatively cheap, therefore organic optical electronic device have obtain relative to inorganic device
The potentiality of cost advantage.In addition, the intrinsic property (such as it is flexible) of organic material can make it be very suitable to concrete application, example
Such as manufacture on flexible substrates.The example of organic optical electronic device includes organic light emitting apparatus (OLED), organic photoelectric crystalline substance
Body pipe, solar battery and organic photodetector.For OLED, organic material can have the property relative to conventional material
It can advantage.For example, the wavelength of organic emission layer transmitting light usually can be adjusted easily with dopant appropriate.
OLED utilizes organic film, and light is emitted when voltage is applied on device.OLED just becomes for such as plate
More and more noticeable technology in display, illumination and backlight application.U.S. Patent No. 5,844,363, the 6,303rd,
Several OLED materials and configuration are described, the patent is incorporated herein in entirety by reference in No. 238 and the 5th, 707, No. 745
In.
One application of phosphorescent emission molecule is full-color display.Professional standard needs for this display are suitable for
Emit the pixel of specific color (referred to as " being saturated " color).Specifically, these standards need red, the green and blue being saturated
Pixel.CIE coordinate well known in the art can be used to measure color.
One example of green emissive molecule is three (2- phenylpyridine) iridium, is expressed as Ir (ppy)3, with following knot
Structure:
In structural formula in this structural formula and herein below, the coordinate bond of (herein, Ir) it will be portrayed as from nitrogen to metal
Straight line.
As used herein, term " organic " includes polymeric material and Small molecule organic materials, can be to have manufactured
Machine optical electron device." small molecule " refer to be not polymer any organic material, and " small molecule " may actually phase
When big.In some cases, small molecule may include repetitive unit.For example, use chain alkyl will not as substituent group
Molecule is removed from " small molecule " classification.Small molecule can also be incorporated into polymer, such as on main polymer chain
Side group or a part as main chain.Small molecule can function as the core of dendritic, the dendroid polymerization
Object is made of a series of chemical shells established on core.The core of dendritic can be fluorescence or phosphorus
Light small molecule emitter.Dendritic can be " small molecule ", and it is believed that currently own used in the field OLED
Dendritic is all small molecule.
As used herein, " top " means farthest from substrate, and " bottom " mean it is nearest from substrate.It is described by first layer
It is " placement " in the case where second layer "upper", first layer is arranged to away from substrate farther out.Unless regulation first layer "AND" second
Layer " contact " otherwise may exist other layers between first and second layer.For example, even if existing between cathode and anode each
Cathode, can be still described as " being placed in " anode "upper" by kind organic layer.
As used herein, " solution can be handled " mean can in the form of solution or suspension in liquid medium dissolution,
Dispersion is conveyed and/or is deposited from liquid medium.
When it is believed that ligand directly facilitates the photo-sensitive characteristic of emissive material, ligand is properly termed as " light sensitivity ".When
It is believed that ligand is properly termed as " complementary " when ligand does not facilitate the photo-sensitive characteristic of emissive material, but complementary match
Position body can change the property of the ligand of light sensitivity.
As used herein, and as those skilled in the art it will be understood that, if the first energy level is closer to vacuum level,
So first " highest occupancy molecular orbit " (HOMO) or " minimum vacant molecular orbit " (LUMO) energy level " being greater than " are " high
In " the 2nd HOMO or lumo energy.It is higher since ionization potential (IP) is measured as the negative energy relative to vacuum level
HOMO energy level corresponds to the IP (less negative IP) with smaller absolute value.Similarly, higher lumo energy corresponds to and has
The electron affinity (EA) (less negative EA) of smaller absolute value.On conventional energy level diagram, vacuum level at top, material
Lumo energy is higher than the HOMO energy level of same material." higher " HOMO or lumo energy are shown as than " lower " HOMO or LUMO energy
Grade is close to the top of this figure.
As used herein, and as those skilled in the art it will be understood that, if the first work function is with higher absolutely
Value, then the first work function " being greater than " or " being higher than " second work function.Because being usually relative to vacuum-energy by power function measuring
The negative of grade, therefore this means that " higher " work function is morely negative.On conventional energy level diagram, vacuum level at top, will " compared with
It is high " work function explanation in a downward direction away from vacuum level farther out.Therefore, the definition of HOMO and lumo energy follows and work content
The different convention of number.
It can find in the U.S. Patent No. being incorporated herein by reference in its entirety 7,279,704 about OLED
With the more details of definition described above.
Summary of the invention
According to one embodiment, a kind of compound is described, the structure with Formulas I:
A-L-B-M-D,
In the structure of Formulas I:
A is selected from the group being made up of:
L is the linking group selected from the group being made up of: singly-bound, has 3- at the aryl with 6-30 carbon atom
The heteroaryl and a combination thereof of 30 carbon atoms；
When L is aryl or heteroaryl, L is optionally further replaced by one or more groups selected from the following: hydrogen, deuterium,
Alkyl, naphthenic base, aralkyl, alkoxy, aryloxy group, amino, silylation, aryl, heteroaryl and a combination thereof；
L-B-M has a structure that
M is selected from the group being made up of: the aryl with 6-30 carbon atom, the heteroaryl with 3-30 carbon atom
And a combination thereof；
M is optionally further replaced by one or more groups selected from the following: hydrogen, deuterium, alkyl, naphthenic base, aralkyl, alkane
Oxygroup, aryloxy group, amino, silylation, aryl, heteroaryl and a combination thereof；
D has a structure that
X is selected from the group being made up of: O, S, Se and CR'R "；
X1、X2、X3、X4、X5、X6、X7、X8、Y1、Y2、Y3、Y4、Y5、Y6、Y7、Y8、Y9、Y10、 Y11、Y12、Z1、Z3、Z4、Z5、
Z6、Z7、Z8、Z11、Z12、Z13、Z14、Z15、Z16、Z17And Z18It is N or CR each independently；
Each R, R' and R " are independently selected from the group being made up of: hydrogen, deuterium, halogen, alkyl, naphthenic base, miscellaneous alkyl,
Aralkyl, alkoxy, aryloxy group, amino, silylation, alkenyl, cycloalkenyl, miscellaneous thiazolinyl, alkynyl, aryl, heteroaryl, acyl group, carbonyl
Base, carboxylic acid group, ester group, isonitrile base, sulfenyl, sulfinyl, sulfonyl, phosphino- and a combination thereof；
Adjacent R substituent group can form fused rings；And
R' and R " can form ring.
In some embodiments, R' and R " form non-aromatic ring.In some embodiments, non-aromatic ring is naphthenic base
Ring.In some embodiments, R' and R " form aromatic ring.
According to another embodiment, a kind of device is also provided, it includes one or more organic light emitting apparatus.It is described one or more
At least one of a organic light emitting apparatus may include anode；Cathode；And it is placed between the anode and the cathode
Organic layer, wherein the organic layer may include compound of formula I, the compound selected from compound 1 to 5 or both.Described device
It can be consumer product, electronic component module, organic light emitting apparatus and/or illumination panel.
According to another embodiment, a kind of composite is provided, containing compound of formula I, selected from the chemical combination of compound 1 to 5
Object or both.
Detailed description of the invention
Fig. 1 illustrates organic light emitting apparatus.
Fig. 2 illustrates the organic light emitting apparatus of the reversing without independent electron supplying layer.
Fig. 3 illustrates Formulas I and substituent A as disclosed herein, the structure of L-B-M and Z.
Specific embodiment
In general, OLED includes at least one for disposing between the anode and the cathode and being electrically connected to anode and cathode
Organic layer.When a current is applied, anode injects hole and cathode injects electrons into organic layer.Institute's injected holes and electronics
Respectively towards the electrode transfer of oppositely charged.When electrons and holes are confined on same molecule, formed " exciton ", for
The localization electron-hole pair of excitation energy state.When exciton is via photoemission mechanism relaxation, emit light.In some feelings
Under condition, exciton can be confined on excimer or exciplex.Non-radiative mechanism (such as thermal relaxation) it can also happen that, but usually
It is considered as undesirable.
Initial OLED uses the emitting molecule from singlet emission light (" fluorescence "), such as such as U.S. Patent No. 4,769,
Disclosed in No. 292, the patent is incorporated in entirety by reference.Fluorescent emission is usually in the time range less than 10 nanoseconds
Middle generation.
Recently, the OLED with the emissive material from triplet transmitting light (" phosphorescence ") has been demonstrated.Ba Erduo
(Baldo) et al. " emit (Highly Efficient from the high efficiency phosphorescent of Organnic electroluminescent device
Phosphorescent Emission from Organic Electroluminescent Devices) ", it is natural
(Nature), volume 395, the 151-154 pages, 1998；(" Ba Erduo-I ") and Ba Erduo et al. " based on electroluminescent phosphorescence
Very efficient green organic light emitting apparatus (Very high-efficiency green organic light-emitting
Devices based on electrophosphorescence) ", Applied Physics journal (Appl.Phys.Lett.), the 75th
Volume, the 3rd phase, are incorporated in entirety by reference by the 4-6 pages (1999) (" Ba Erduo-II ").It is herein incorporated by reference
U.S. Patent No. No. 7,279,704 5-6 column in phosphorescence is more fully described.
Fig. 1 illustrates organic light emitting apparatus 100.Figure is not drawn necessarily to scale.Device 100 may include substrate 110, sun
Pole 115, hole injection layer 120, hole transporting layer 125, electronic barrier layer 130, emission layer 135, hole blocking layer 140, electronics
Transfer layer 145, electron injecting layer 150, protective layer 155, cathode 160 and barrier layer 170.Cathode 160 is that have the first conductive layer
162 and second conductive layer 164 composite cathode.Device 100 can be manufactured by layer described in deposited in sequential.With reference
The US 7,279,704 that is incorporated to of mode 6-10 column in the property of these various layers and example materials is more fully described
And function.
Each of these layers have more examples.For example, the U.S. Patent No. being incorporated in entirety by reference
Flexible and transparent substrate-anode combination is disclosed in No. 5,844,363.Through p doping hole transporting layer example be with
The molar ratio of 50:1 is doped with F4The m-MTDATA of-TCNQ, the U.S. Patent application being such as incorporated in entirety by reference are public
It opens disclosed in case the 2003/0230980th.What is be incorporated in entirety by reference gives thompson (Thompson) et al.
U.S. Patent No. 6,303,238 in the example of emissive material and material of main part is disclosed.The reality of electron supplying layer through n doping
Example is the BPhen with the molar ratio of 1:1 doped with Li, the Patent Application Publication being such as incorporated in entirety by reference
Disclosed in No. 2003/0230980.The U.S. Patent No. being incorporated in entirety by reference 5,703,436 and the 5th,
707, No. 745 disclose the example of cathode comprising with the thin metal layer such as Mg:Ag with above cover it is transparent, conductive, through splashing
The composite cathode of the ITO layer of plated deposition.The U.S. Patent No. being incorporated in entirety by reference 6,097,147 and United States Patent (USP)
The principle and use on barrier layer are more fully described in application publication the 2003/0230980th.In entirety by reference simultaneously
The example of implanted layer is provided in the Patent Application Publication entered the 2004/0174116th.It can be in the side to be cited in full text
The description of protective layer is found in the Patent Application Publication that formula is incorporated to the 2004/0174116th.
Fig. 2 illustrates the OLED 200 of reversing.Described device includes that substrate 210, cathode 215, emission layer 220, hole are defeated
Send layer 225 and anode 230.Device 200 can be manufactured by layer described in deposited in sequential.Because of most common OLED configuration
With the cathode being placed on anode, and device 200 has the cathode 215 being placed under anode 230, so device 200 can
Referred to as " to reverse " OLED.In the respective layer of device 200, it can be used similar with the material described in device 100
Material.Fig. 2 is provided can be how from some layers of incomplete structure of an example of device 100.
Simple layered structure illustrated in Fig. 1 and 2 is provided as non-limiting example, and it will be understood that can tie
It closes various other structures and uses the embodiment of the present invention.It is exemplary on described specific material and structural nature
, and other materials and structure can be used.It can be based on design, performance and cost factor, by combining in different ways
Described each layer realizes functional OLED, or can be completely omitted several layers.It can also include its not specifically described
Its layer.The material of the material different from specifically describing can be used.Although many examples in examples provided herein will be each
Kind layer is described as comprising homogenous material, it should be appreciated that the combination (such as mixture of main body and dopant) of material can be used
Or more generally, mixture.Also, the layer can have each seed layer.Each layer of title is given herein to be not intended to
With stringent restricted.For example, in device 200, hole transporting layer 225 conveys hole and injects holes into transmitting
In layer 220, and hole transporting layer or hole injection layer can be described as.In one embodiment, OLED can be described
For with " organic layer " being placed between cathode and anode.This organic layer may include single layer, or can further include
Such as multiple layers of such as different organic materials described in Fig. 1 and 2.
It can also use the structure and material that does not specifically describe, such as the OLED (PLED) comprising polymeric material, such as with
What the mode being cited in full text was incorporated to gives disclosed in U.S. Patent No. 5,247,190 of Fleder (Friend) et al..Make
For another example, the OLED with single organic layer can be used.OLED can be stacked, such as in entirety by reference simultaneously
Described in No. 5,707,745 for giving welfare this special (Forrest) et al. entered.OLED structure can be detached from Fig. 1 and 2
Illustrated simple layered structure.For example, substrate may include angled reflecting surface to improve out coupling (out-
Coupling mesa structure described in U.S. Patent No. 6,091,195 of welfare this top grade people), such as is such as given, and/or
Such as give concave point structure described in U.S. Patent No. 5,834,893 of Bu Liweike (Bulovic) et al., the patent with
The mode being cited in full text is incorporated to.
Unless specified otherwise herein, any one of the layer of various embodiments otherwise can be deposited by any appropriate method.
For organic layer, preferred method include thermal evaporation, ink-jet (such as the U.S. Patent No. 6 being incorporated in entirety by reference,
Described in No. 013,982 and No. 6,087,196), organic vapor phase deposition (OVPD) (such as is incorporated in entirety by reference
Described in U.S. Patent No. 6,337,102 for giving welfare this top grade people) and pass through organic vapor jet printing (OVJP)
It deposits (such as described in U.S. Patent No. being incorporated in entirety by reference 7,431,968).Other suitable deposition methods
Including spin coating and other techniques based on solution.Technique based on solution preferably carries out in nitrogen or inert atmosphere.For other
Layer, preferred method includes thermal evaporation.Preferred patterning method includes by the deposition of mask, cold welding (such as to be cited in full text
Mode be incorporated to U.S. Patent No. No. 6,294,398 and No. 6,468,819 described in) and it is heavy with such as ink-jet and OVJD etc.
The associated patterning of certain methods in product method.Other methods can also be used.Material to be deposited can be modified, so that
It is compatible with specific deposition method.For example, can in small molecule using tool branch or it is unbranched and preferably comprise to
The substituent group such as alkyl and aryl of few 3 carbon, to enhance the ability that it is subjected to solution processing.Can be used with 20 or
The substituent group of more carbon, and 3-20 carbon is preferred scope.Material with dissymmetrical structure can be than with symmetrical junction
The material of structure has better solution processability, because asymmetric material can have lower recrystallization tendentiousness.It can be with
Enhance the ability that small molecule is subjected to solution processing using dendritic substituent group.
The device manufactured according to embodiments of the present invention can optionally further include barrier layer.One purposes of barrier layer
Guard electrode and organic layer from due to harmful substance (including moisture, steam and/or the gas etc.) being exposed in environment by
Damage.Barrier layer can be deposited on substrate, on electrode, be deposited under substrate, electrode or be deposited on substrate, by electrode, or be deposited on
On any other part (including edge) of device.Barrier layer may include single layer or multiple layers.Barrier layer can be by each
Chemical vapour deposition technique known to kind is formed, and may include the composition with single-phase and the group with multiple phases
Close object.Any suitable material or combination of materials may be used to barrier layer.Barrier layer can incorporate inorganic compound or organic
Compound or both.Preferred barrier layer includes the mixture of polymeric material and non-cohesive material, such as in entirety by reference
The U.S. Patent No. being incorporated herein 7,968,146, PCT Patent Application the PCT/US2007/023098th and PCT/
Described in No. US2009/042829.In order to be considered as " mixture ", the aforementioned polymeric materials and non-cohesive material of barrier layer are constituted
It should deposit under the same reaction conditions and/or at the same time.Polymeric material can arrive the weight rate of non-cohesive material in 95:5
In the range of 5:95.Polymeric material and non-cohesive material can be generated by same precursor material.In an example, polymeric material
It is substantially formed by polymerizeing silicon and inorganic silicon with the mixture of non-cohesive material.
The device of embodiment according to the present invention manufacture can be incorporated into diversified electronic component module (or unit)
In, the electronic component module can be incorporated into a variety of electronic products or intermediate module.The electronic product or intermediate module
Example include the display screen that can be utilized for end user product manufacturer, lighting device (such as discrete light source device or photograph
Bright panel) etc..The electronic component module can optionally include drive electronics and/or power supply.Reality according to the present invention
The device for applying example manufacture can be incorporated into diversified consumer product, and the consumer product has one or more electronics groups
Part module (or unit) is incorporated into wherein.The consumer product will include comprising one or more light sources and/or one or more certain
Any kind of product of the visual displays of one type.Some examples of the consumer product include flat-panel monitor, meter
Calculation machine monitor, medical monitors, television set, billboard, the lamp for internal or external illumination and/or signalling, head-up are aobvious
Show device, all-transparent or partially transparent display, flexible display, laser printer, phone, mobile phone, tablet computer, plate hand
Machine, personal digital assistant (PDA), laptop computer, digital camera, Video Camera, view finder, micro-display, 3-D are shown
Device, delivery vehicle, large area wall, theater or stadium screen or direction board.Various controlling mechanisms can be used to control root
The device manufactured according to the present invention, including passive matrix and active matrix.It is intended to for many devices in described device being used for pair
For the mankind in comfortable temperature range, such as 18 degrees Celsius to 30 degrees Celsius, and more preferably (20-25 is Celsius at room temperature
Degree), but (such as -40 degrees Celsius to+80 degrees Celsius) can be used outside this temperature range.
Material described herein and structure can be applied in the device different from OLED.For example, for example, it is organic too
The material and structure can be used in positive energy other photoelectron devices such as battery and organic photodetector.More generally, such as
The material and structure can be used in the organic devices such as organic transistor.
As used herein, term " halogen ", " halogen " or " halide " includes fluorine, chlorine, bromine and iodine.
As used herein, term " alkyl " covers straight chain and branched alkyl.Preferred alkyl is containing one to ten five carbon
The alkyl of atom, and including methyl, ethyl, propyl, isopropyl, butyl, isobutyl group, tert-butyl etc..In addition, alkyl can be
It is optionally substituted.
As used herein, term " naphthenic base " covers cyclic alkyl.Preferred naphthenic base is containing 3 to 7 carbon atoms
Naphthenic base, and including cyclopropyl, cyclopenta, cyclohexyl etc..In addition, naphthenic base can be and be optionally substituted.
As used herein, term " alkenyl " covers straight chain and branched-chain alkenyl.Preferred alkenyl is containing two to ten five carbon
The alkenyl of atom.In addition, alkenyl can be and be optionally substituted.
As used herein, term " alkynyl " covers straight chain and branch alkynyl.Preferred alkynyl is containing two to ten five carbon
The alkynyl of atom.In addition, alkynyl can be and be optionally substituted.
As used herein, term " aralkyl " or " aryl alkyl " are interchangeably used and cover with aromatic group
Alkyl as substituent group.In addition, aralkyl can be and be optionally substituted.
As used herein, term " heterocycle " covers aromatic series and non-aromatic cyclic group.Heteroaromatic ring-type group
Also mean heteroaryl.Preferred non aromatic heterocyclyl is containing the heterocycle including at least one heteroatomic 3 or 7 annular atom
Base, and including cyclammonium, such as morpholinyl, piperidyl, pyrrolidinyl etc. and cyclic ethers, such as tetrahydrofuran, oxinane etc..
In addition, heterocycle can be and be optionally substituted.
As used herein, term " aryl " or " aromatic group " cover monocyclic groups and multi-loop system.It is polycyclic to have
There are two or more two of them carbon be the shared ring of two adjacent rings (ring is " condensed "), wherein in the ring
At least one is aromatic, such as other rings can be naphthenic base, cycloalkenyl, aryl, heterocycle and/or heteroaryl.In addition, fragrant
Base, which can be, to be optionally substituted.
As used herein, it may include one to three heteroatomic monocyclic heteroaromatic groups that term " heteroaryl ", which is covered,
Such as pyrroles, furans, thiophene, imidazoles, oxazole, thiazole, triazole, pyrazoles, pyridine, pyrazine and pyrimidine etc..Term heteroaryl also wraps
Including with two or more two of them atoms is the polycyclic miscellaneous of the shared ring of two adjacent rings (ring is " condensed ")
Aromatic systems, wherein at least one of described ring is heteroaryl, such as other rings can be naphthenic base, cycloalkenyl, aryl,
Heterocycle and/or heteroaryl.In addition, heteroaryl can be and be optionally substituted.
Alkyl, naphthenic base, alkenyl, alkynyl, aralkyl, heterocycle, aryl and heteroaryl can be optionally by one or more
Substituent group selected from the group being made up of replaces: hydrogen, deuterium, halogen, alkyl, naphthenic base, miscellaneous alkyl, aralkyl, alkoxy,
Aryloxy group, amino, ring type amidogen, silylation, alkenyl, cycloalkenyl, miscellaneous thiazolinyl, alkynyl, aryl, heteroaryl, acyl group, carbonyl, carboxylic acid
Base, ether, ester group, itrile group, isonitrile base, sulfenyl, sulfinyl, sulfonyl, phosphino- and a combination thereof.
As used herein, " substituted " to indicate, it is not that the substituent group of H is bonded to relevant position, such as carbon.Therefore, it lifts
For example, in R1When being mono-substituted, then a R1It must not be H.Similarly, in R1When being replaced by two, then two R1Must not be
H.Similarly, in R1When unsubstituted, R1It is all hydrogen for all available positions.
" azepine " title in segment (i.e. azepine-dibenzofurans, azepine-dibenzothiophenes etc.) as described herein means
One or more C-H groups in segment out of the ordinary can be replaced by nitrogen-atoms, such as and property without any restrictions, azepine triphenylene
Cover dibenzo [f, h] quinoxaline and dibenzo [f, h] quinoline.Those skilled in the art can easily envision above
The other nitrogen analogs of the azepine-derivative, and all these analogs are intended to by term such as described herein
Cover.
It should be understood that when molecule fragment to be described as substituent group or be alternatively attached to another part, title can be as
It is segment (such as phenyl, phenylene, naphthalene, dibenzofuran group) it is general or as its be entire molecule (such as benzene, naphthalene,
Dibenzofurans) generally write.As used herein, the mode of these different name substituent groups or the segment of connection is considered as
Effect.
According to one embodiment, a kind of compound is described, the structure with Formulas I:
A-L-B-M-D,
In the structure of Formulas I:
A is selected from the group being made up of:
L is the linking group selected from the group being made up of: singly-bound, has 3- at the aryl with 6-30 carbon atom
The heteroaryl and a combination thereof of 30 carbon atoms；
When L is aryl or heteroaryl, L is optionally further replaced by one or more groups selected from the following: hydrogen, deuterium,
Alkyl, naphthenic base, aralkyl, alkoxy, aryloxy group, amino, silylation, aryl, heteroaryl and a combination thereof；
L-B-M has a structure that
Wherein M is selected from the group that is made up of: aryl with 6-30 carbon atom, miscellaneous with 3-30 carbon atom
Aryl and a combination thereof；
M is optionally further replaced by one or more groups selected from the following: hydrogen, deuterium, alkyl, naphthenic base, aralkyl, alkane
Oxygroup, aryloxy group, amino, silylation, aryl, heteroaryl and a combination thereof；
D has a structure that
X is selected from the group being made up of: O, S, Se and CR'R "；
X1、X2、X3、X4、X5、X6、X7、X8、Y1、Y2、Y3、Y4、Y5、Y6、Y7、Y8、Y9、Y10、 Y11、Y12、Z1、Z3、Z4、Z5、
Z6、Z7、Z8、Z11、Z12、Z13、Z14、Z15、Z16、Z17And Z18It is N or CR each independently；
Each R, R' and R " are independently selected from the group being made up of: hydrogen, deuterium, halogen, alkyl, naphthenic base, miscellaneous alkyl,
Aralkyl, alkoxy, aryloxy group, amino, silylation, alkenyl, cycloalkenyl, miscellaneous thiazolinyl, alkynyl, aryl, heteroaryl, acyl group, carbonyl
Base, carboxylic acid group, ester group, isonitrile base, sulfenyl, sulfinyl, sulfonyl, phosphino- and a combination thereof；
Adjacent R substituent group can form fused rings；And
R' and R " can form ring.
In some embodiments, R' and R " form non-aromatic ring.In some embodiments, non-aromatic ring is naphthenic base
Ring.In some embodiments, R' and R " form aromatic ring.
In some embodiments, X is S.
In some embodiments, X1To X8At least one of be N.In some embodiments, X1-X8One of be N.
In some embodiments, X1-X4One of be N, and X5-X8It is C.In some embodiments, X5-X8One of be N, and
And X1-X4It is C.
In some embodiments, Y1To Y12At least one of be N.In some embodiments, Y1-Y12One of be N.
In some embodiments, Y5-Y12At least one of be N.In some embodiments, Y5-Y8One of be N.In some implementations
In example, Y5-Y8One of be N, Y8-Y12It is C.In some embodiments, Y1-Y4Each of be C.
In some embodiments, Z1、Z3、Z4、Z5、Z6、Z7And Z8At least one of be N.In some embodiments, Z1、
Z3、Z4、Z5、Z6、Z7And Z8One of be N.In some embodiments, Z1、Z3And Z4One of be N, and Z5、Z6、Z7With
Z8It is C.In some embodiments, Z5、Z6、Z7And Z8One of be N, and Z1、Z3、Z4It is C.
In some embodiments, Z11To Z18At least one of be N.In some embodiments, Z11-Z18One of be
N.In some embodiments, Z11-Z14One of be N, and Z15-Z18It is C.
In some embodiments, A is selected from the group being made up of:
In some embodiments, L is selected from the group being made up of:
Singly-bound (L1),
L22 and L23.
In some embodiments, B is selected from the group being made up of:
In some embodiments, M is selected from the group being made up of:
In some embodiments, D is selected from the group being made up of:
In some embodiments, the compound is selected from the group being made up of:
In other embodiments, a kind of compound is disclosed, compound 1 to 5 is selected from.
According to another aspect of the present invention, a kind of device is also provided comprising one or more organic light emitting apparatus.It is described
At least one of one or more organic light emitting apparatus may include anode；Cathode；Be placed in the anode and the cathode
Between organic layer.The organic layer may include one or more emitter dopants.The emitter dopant can be phosphorus
Photodopant and/or fluorescent dopants.The organic layer may include as described herein according to the compound of Formulas I and its change
Body is as main body.Alternatively or in addition, the organic layer may include compound selected from the group below as main body: as described herein
Compound 1 to 5.
Described device can be one or more of following: consumer product, electronic component module, organic light emitting apparatus and
Illumination panel.
In some embodiments, the organic layer is emission layer, and compound of formula I or the chemical combination selected from compound 1 to 5
Object is main body.
In some embodiments, the organic layer further includes phosphorescent emissions dopant, wherein the phosphorescent emissions are mixed
Miscellaneous dose be a part with the ligand at least one ligand or when the ligand is more than bidentate transition
Metal complex, the ligand are selected from the group being made up of:
Wherein Ra、Rb、RcAnd RdIt can indicate monosubstituted base, disubstituted, three substituent groups or four substituent groups or unsubstituted
Base；
Wherein Ra、Rb、RcAnd RdIndependently selected from the group being made up of: hydrogen, deuterium, halogen, alkyl, naphthenic base, miscellaneous alkane
Base, aralkyl, alkoxy, aryloxy group, amino, silylation, alkenyl, cycloalkenyl, miscellaneous thiazolinyl, alkynyl, aryl, heteroaryl, acyl group,
Carbonyl, carboxylic acid group, ester group, itrile group, isonitrile base, sulfenyl, sulfinyl, sulfonyl, phosphino- and a combination thereof；And
Wherein Ra、Rb、RcAnd RdIn two adjacent substituents optionally engage to form fused rings or form multiple tooth coordination
Body.
In some embodiments, the organic layer is barrier layer, and the compound of formula I is the resistance in the organic layer
Obstructing material.In some embodiments, the organic layer is electron supplying layer, and the compound with Formulas I is that described have
Electron transport materials in machine layer.
In another aspect of the invention, a kind of composite is described, it includes the chemical combination disclosed herein according to Formulas I
Object and its variant.A kind of composite is also described, it includes the compounds that compound 5 is arrived selected from compound 1.The composite can be with
Including one or more components disclosed herein selected from the group being made up of: solvent, main body, hole-injecting material,
Hole transporting material and electron transport layer material.
With the combination of other materials
Be described herein as can be used for the specific layer in organic light emitting apparatus material can be present in described device
A variety of other materials are applied in combination.For example, transmitting dopant disclosed herein can be with a variety of main bodys, transfer layer, resistance
Barrier, implanted layer, electrode and other layers that may be present are used in combination.The material for being described below or referring to is can be with this paper institute
The non-limiting example for the material that disclosed compound combination uses, and those skilled in the art can easily consulting literatures
To identify the other materials that can be applied in combination.
HIL/HTL:
Hole used in the present invention is injected/is conveyed material and is not particularly limited, and any compound can be used, only
Want compound typically serve as hole inject/convey material.The example of the material includes but is not limited to: phthalocyanine or porphin
Quinoline derivant；Aromatic amine derivative；Indolocarbazole derivatives；Polymer containing fluorohydrocarbon；Conductive dopant
Polymer；Conducting polymer, such as PEDOT/PSS；The self assembly list of compound derived from such as phosphonic acids and silane derivative
Body；Metal oxide derivative, such as MoOx；P-type semiconductor organic compound, such as Isosorbide-5-Nitrae, 5,8,9,12- six azepine Sanyas
Benzene pregnancy nitrile；Metal complex and crosslinkable.
The example of aromatic amine derivative used in HIL or HTL includes but is not limited to following general formula structure:
Ar1To Ar9Each of selected from the group that is made of aromatic hydrocarbon cycle compound, such as benzene, biphenyl, terphenyl,
Triphenylene, naphthalene, En, Fu, phenanthrene, fluorenes, pyrene, lettuce, Azulene；The group being made of aromatic heterocyclic compounds, such as dibenzo thiophene
Pheno, dibenzofurans, dibenzo selenophen, furans, thiophene, benzofuran, benzothiophene, benzo selenophen, carbazole, indoles and click
Azoles, two pyridine of pyrrolo-, pyrazoles, imidazoles, triazole, oxazole, thiazole, oxadiazoles, dislikes triazole, dioxazole, thiophene two at pyridyl group indoles
Azoles, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazines, evil thiazine, oxadiazines, indoles, benzimidazole, indazole, indoles and oxazines,
Benzoxazoles, benzo isoxazole, benzothiazole, quinoline, isoquinolin, cinnolines, quinazoline, quinoxaline, naphthyridines, phthalazines, pyridine of talking endlessly, two
Benzo piperazine mutters, acridine, azophenlyene, phenthazine, phenoxazine, benzofuran and pyridine, furans and two pyridines, benzothiophene and pyridine,
Two pyridine of thieno, benzo selenophen and pyridine and selenophen and two pyridines；With the group being made of 2 to 10 cyclic structural units,
The structural unit is same type or different types of group selected from aromatic cyclic hydrocarbon group and aromatic heterocycle, and straight
Connect or via in oxygen atom, nitrogen-atoms, sulphur atom, silicon atom, phosphorus atoms, boron atom, chain structural unit and aliphatic ring group extremely
Few one is bonded each other.Wherein each Ar is further chosen replace from the substituent group of group being made up of: hydrogen, deuterium, halogen,
Alkyl, naphthenic base, miscellaneous alkyl, aralkyl, alkoxy, aryloxy group, amino, silylation, alkenyl, cycloalkenyl, miscellaneous thiazolinyl, alkynyl,
Aryl, heteroaryl, acyl group, carbonyl, carboxylic acid group, ester group, itrile group, isonitrile base, sulfenyl, sulfinyl, sulfonyl, phosphino- and its group
It closes.
In one aspect, Ar1To Ar9Independently selected from the group being made up of:
Wherein k is 1 to 20 integer；X101To X108It is C (including CH) or N；Z101It is NAr1, O or S； Ar1More than having
The identical group of definition.
The example of metal complex used in HIL or HTL includes but is not limited to following general formula:
Wherein Met is metal, can have the atomic wts greater than 40；(Y101-Y102) it is bidentate ligands, Y101With
Y102Independently selected from C, N, O, P and S；L101It is complementary ligand；K' is 1 to the maximum ligand number that can connect with metal
Integer value；And k'+k " is the maximum ligand number that can be connect with metal.
In one aspect, (Y101-Y102) it is 2- phenylpyridine derivative.On the other hand, (Y101-Y102) it is carbene ligands
Body.On the other hand, Met is selected from Ir, Pt, Os and Zn.On the other hand, metal complex has opposite less than about 0.6V
In Fc+/ Fc pairs of solution state minimum oxidizing potential.
Main body:
The luminescent layer of organic el device of the invention preferably at least contains metal complex as luminescent material, and can
To contain the material of main part for using metal complex as dopant material.The example of material of main part is not particularly limited, and
Any metal complex or organic compound can be used, as long as the triplet energies of main body are greater than the triplet energies of dopant
?.Although material of main part is classified as the device for being preferred for emitting various colors by following table, any main body material can be used
Material and any dopant, as long as meeting triplet criterion.
The example of metal complex as main body preferably has following general formula:
Wherein Met is metal；(Y103-Y104) it is bidentate ligands, Y103And Y104Independently selected from C, N, O, P and S；L101
It is another ligand；K' is 1 integer value for arriving the maximum ligand number that can be connect with metal；And k'+k " is can be with gold
Belong to the maximum ligand number of connection.
In one aspect, metal complex is:
Wherein (O-N) is with the bidentate ligands with the metal of O and N Atomic coordinate.
On the other hand, Met is selected from Ir and Pt.On the other hand, (Y103-Y104) it is carbene ligands.
The example of organic compound as main body is selected from the group being made of aromatic hydrocarbon cycle compound, such as benzene, connection
Benzene, terphenyl, triphenylene, naphthalene, En, Fu, phenanthrene, fluorenes, pyrene, lettuce, Azulene；The group being made of aromatic heterocyclic compounds, such as
Dibenzothiophenes, dibenzofurans, dibenzo selenophen, furans, thiophene, benzofuran, benzothiophene, benzo selenophen, carbazole, Yin
Diindyl and carbazole, pyridyl group indoles, two pyridine of pyrrolo-, pyrazoles, imidazoles, triazole, oxazole, thiazole, oxadiazoles, evil triazole, two evils
Azoles, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazines, dislikes thiazine, oxadiazines, indoles, benzimidazole, indazole, indoles at thiadiazoles
And oxazines, benzoxazoles, benzo isoxazole, benzothiazole, quinoline, isoquinolin, cinnolines, quinazoline, quinoxaline, naphthyridines, phthalazines,
Talk endlessly pyridine, dibenzo piperazine mutter, acridine, azophenlyene, phenthazine, phenoxazine, benzofuran and pyridine, furans and two pyridines, benzothiophene
And pyridine, two pyridine of thieno, benzo selenophen and pyridine and selenophen and two pyridines；It is formed with by 2 to 10 cyclic structural units
Group, the structural unit is same type selected from aromatic cyclic hydrocarbon group and aromatic heterocycle or different types of base
Group, and directly or via oxygen atom, nitrogen-atoms, sulphur atom, silicon atom, phosphorus atoms, boron atom, chain structural unit and aliphatic ring
At least one of base is bonded each other.Wherein each group is further chosen replace from the substituent group for the group being made up of:
It is hydrogen, deuterium, halogen, alkyl, naphthenic base, miscellaneous alkyl, aralkyl, alkoxy, aryloxy group, amino, silylation, alkenyl, cycloalkenyl, miscellaneous
Alkenyl, alkynyl, aryl, heteroaryl, acyl group, carbonyl, carboxylic acid group, ester group, itrile group, isonitrile base, sulfenyl, sulfinyl, sulfonyl,
Phosphino- and a combination thereof.
In one aspect, host compound contains at least one of following group in the molecule:
Wherein R101To R107Independently selected from the group being made up of: hydrogen, deuterium, halogen, alkyl, naphthenic base, miscellaneous alkyl,
Aralkyl, alkoxy, aryloxy group, amino, silylation, alkenyl, cycloalkenyl, miscellaneous thiazolinyl, alkynyl, aryl, heteroaryl, acyl group, carbonyl
Base, carboxylic acid group, ester group, itrile group, isonitrile base, sulfenyl, sulfinyl, sulfonyl, phosphino- and a combination thereof, when it is aryl or heteroaryl
When base, there is the definition similar with above-mentioned Ar.K is 0 to 20 or 1 to 20 integer；K ' " is 0 to 20 integer.X101It arrives
X108Selected from C (including CH) or N.Z101And Z102Selected from NR101, O or S.
HBL:
Hole blocking layer (HBL) can be to reduce hole and/or the number of exciton of leaving emission layer.Stop with lacking
The similar device of layer is compared, and the presence of this barrier layer in a device can produce substantial higher efficiency.In addition, barrier layer
It can be the wanted region for being limited to OLED will be emitted.
In one aspect, compound used in HBL contains identical molecule or same functional group as aforementioned body.
On the other hand, compound used in HBL contains at least one of following group in the molecule:
Wherein k is 1 to 20 integer；L101It is another ligand, k' is 1 to 3 integer.
ETL:
Electron supplying layer (ETL) may include the material that can convey electronics.Electron supplying layer can be (not mixing for essence
It is miscellaneous) or it is doped.Doping can be to enhance electric conductivity.The example of ETL material is not particularly limited, and can be used
Any metal complex or organic compound, as long as it is typically to convey electronics.
In one aspect, compound used in ETL contains at least one of following group in the molecule:
Wherein R101Selected from the group being made up of: hydrogen, deuterium, halogen, alkyl, naphthenic base, miscellaneous alkyl, aralkyl, alcoxyl
Base, aryloxy group, amino, silylation, alkenyl, cycloalkenyl, miscellaneous thiazolinyl, alkynyl, aryl, heteroaryl, acyl group, carbonyl, carboxylic acid group, ester
Base, itrile group, isonitrile base, sulfenyl, sulfinyl, sulfonyl, phosphino- and a combination thereof have when it is aryl or heteroaryl
The definition similar with above-mentioned Ar.Ar1To Ar3With the definition similar with above-mentioned Ar.K is 1 to 20 integer.X101To X108Selected from C
(including CH) or N.
On the other hand, metal complex used in ETL includes but is not limited to following general formula:
Wherein (O-N) or (N-N) is the bidentate ligands with the metal being coordinated with atom O, N or N, N；L101It is another
Ligand；K' is 1 integer value for arriving the maximum ligand number that can be connect with metal.
In any of above compound used in each layer of OLED device, hydrogen atom can partly or completely perdeuterated.
Therefore, any substituent group (such as (but not limited to) methyl, phenyl, pyridyl group etc.) specifically listed covers its non-deuterate, part
Deuterate and complete deuterated form.Similarly, substituent group classification (such as (but not limited to) alkyl, aryl, naphthenic base, heteroaryl etc.)
It is also covered by its non-deuterate, part deuterate and complete deuterated form.
It is combined in addition to materials disclosed herein and/or with materials disclosed herein, many can also be used in OLED
Hole-injecting material, hole transporting material, material of main part, dopant material, exciton/hole barrier layer material, electron transport material
Material and electron injection material.The non-limiting example for the material in OLED can be combined with materials disclosed herein under
It is listed in Table A.Table A is listed described in the non-limiting classification of material, the non-limiting example of the other compound of every type and disclosure
The bibliography of material.
Table A
Experiment
Synthesize example
Synthesize compound A1-L1-B1-M2-D1
By 2- (3- (9H- carbazole -9- base) phenyl) -9H- carbazole (3.50g, 8.57mmol), 2- bromine dibenzo [b, d] thiophene
Pheno (2.255 g, 8.57mmol), three (dibenzylideneacetone) two palladiums (0) (0.157g, 0.171mmol), dicyclohexyl (2',
6'- dimethoxy-[1,1'- biphenyl] -2- base) phosphine (0.211g, 0.514mmol) and 2- methyl propyl- 2- acid sodium (1.647g,
17.14mmol) solution in dimethylbenzene (100mL) flows back 16 hours under a nitrogen.Thermal reaction mixture is passed through shortPlug filtering, and then evaporate solvent.Thick material is passed through on silica gel with heptane/DCM (1/1, v/v) as elution
Agent carries out column chromatography to purify, and is then recrystallized by toluene/ethanol, obtains the compound A1-L1- of white solid-like
B1-M2-D1 (2.1g, 42%).
Synthesize compound A4-L1-B1-M2-D1
By 2- (3- (9H- carbazole -9- base) phenyl) -9H- carbazole (3.50g, 8.57mmol), 2- bromine triphenylene (3.16g,
10.28 mmol), three (dibenzylideneacetone) two palladiums (0) (0.157g, 0.171mmol), dicyclohexyl (2', 6'- dimethoxy
Base-[1,1'- biphenyl] -2- base) phosphine (0.211g, 0.514mmol) and 2- methyl propyl- 2- acid sodium (1.647g, 17.14mmol)
Solution in dimethylbenzene (150 mL) flows back 16 hours under a nitrogen.Thermal reaction mixture is passed through shortPlug filtering,
And then evaporate solvent.By thick material by carrying out column as eluant, eluent with heptane/methylene chloride (1/1, v/v) on silica gel
Then chromatography is recrystallized to purify by heptane/methylene chloride, obtain the compound A4-L1-B1-M2- of white solid-like
D1 (3.5 g, 64%).
Synthesize compound 5
By 3- (3- (9H- carbazole -9- base) phenyl) -9H- carbazole (7g, 17.14mmol), 2- bromine triphenylene (4.74g,
15.42 mmol), 2- methyl propyl- 2- acid sodium (3.29g, 34.3mmol), three (dibenzylideneacetone) two palladiums (0) (0.235g,
0.257 mmol) and dicyclohexyl (2', 6'- dimethoxy-[1,1'- biphenyl] -2- base) phosphine (0.211g, 0.514mmol) in
Solution in dimethylbenzene (120 ml) flows back 16 hours under a nitrogen.Thermal reaction mixture is passed through shortPlug filtering, and
And then evaporate solvent.By thick material by carrying out column color as eluant, eluent with heptane/methylene chloride (1/1, v/v) on silica gel
Then spectrum is recrystallized to purify by toluene/ethanol, obtain the compound 5 (5.1g, 47%) of white solid-like.
Device example
All OLED devices all pass through high vacuum (about 10-7Support) thermal evaporation manufacture.Anode electrode is the tin indium oxide of 80nm
(ITO).Cathode electrode is made of the LiF of 1nm followed by the Al of 100nm.After the fabrication, by all devices immediately with through epoxy
The glass cover of resin seal is encapsulated in the nitrogen glove box (H of < 1ppm2O and O2) in, and moisture absorption gas agent is incorporated into packaging
Portion.
1. first device of device has the organic stacking being sequentially made up of from the surface ITO: the LG101 of 10nm (comes
It is chemical (LG Chem) from LG) it is used as hole injection layer (HIL), bis- [N- (1- the naphthalene)-N- phenyl amino biphenyl of 4, the 4'- of 30nm
(NPD) emission layer (EML) of hole transporting layer (HTL) and 30nm are used as.On the top of EML, the compound BL of 5nm is deposited
As hole blocking layer (HBL), followed by three (8-hydroxyquinoline base) aluminium (Alq of 45nm3) it is used as electron supplying layer (ETL).
EML is grouped as by two kinds of groups: the A1-L1-B1-M2-D1 of 90 weight % is used as main body, and the GD of 10 weight % is as transmitting
Dopant.The chemical structure of compound used therefor is presented below.
2. device 2 of device has structure identical with device 1, the difference is that compound A4-L1-B1-M2-D1 is used
Make main body.
3. device 3 of device has structure identical with device 1, the difference is that compound 5 is used as main body.
Device C-1. device C-1 has structure identical with device 1, the difference is that compound CC-1 is used as main body.
The following table 1 is the general introduction of device data.External quantum efficiency (EQE) is recorded under 1000 nits, and is defined as device
Decay to the service life (LT the time required to the 80% of 1000 nit original intensities80) when by hypothesis accelerated factor being 1.8 in 40 mA/
cm2The value measured under constant current density calculates.Lifetime data is standardized as to the lifetime data of device 1.
All devices all emit green tint.As shown in table 1, compared with using compound CC-1 as material of main part
Device C-1 is compared, and the compounds of this invention is used to show higher efficiency and more long-life as the device 1,2 and 3 of material of main part.
This shows the linking group (such as benzene) between two carbazole moieties in terms of the material property for enhancing host compound of the present invention
It plays a crucial role.The possible explanation of one kind is that the improvement is due to caused by the unique chemical moieties due to the compounds of this invention
The electrons flux more balanced.
It should be understood that various embodiments described herein is only used as example, and it is not intended to limit the scope of the present invention.Citing comes
It says, many in material described herein and structure can be replaced with other materials and structure, without departing from essence of the invention
Mind.Therefore the invention as claimed may include the variation of specific example as described herein and preferred embodiment, such as this field
Technical staff is readily apparent that.It should be understood that being not intended to be restrictive about the various the theories why present invention works.
Claims (13)
1. a kind of compound, the structure with Formulas I:
A-L-B-M-D,
Wherein A is selected from the group being made up of:
Wherein L is singly-bound；
Wherein L-B-M has a structure that
Wherein M is selected from the group being made up of: the aryl with 6-30 carbon atom, the heteroaryl with 3-30 carbon atom
And a combination thereof；
Wherein M is optionally further replaced by one or more groups selected from the following: hydrogen, deuterium, alkyl, naphthenic base, aralkyl, alkane
Oxygroup, aryloxy group, amino, silylation, aryl, heteroaryl and a combination thereof；
Wherein D has a structure that
Wherein X is selected from the group being made up of: O, S, Se and CR'R "；
Wherein X1、X2、X3、X4、X5、X6、X7、X8、Y1、Y2、Y3、Y4、Y5、Y6、Y7、Y8、Y9、Y10、Y11、Y12、Z1、Z3、Z4、Z5、Z6、
Z7、Z8、Z11、Z12、Z13、Z14、Z15、Z16、Z17And Z18It is N or CR each independently；And
Wherein each R, R' and R " are independently selected from the group being made up of: hydrogen, deuterium, halogen, alkyl, naphthenic base, miscellaneous alkyl,
Aralkyl, alkoxy, aryloxy group, amino, silylation, alkenyl, cycloalkenyl, miscellaneous thiazolinyl, alkynyl, aryl, heteroaryl, acyl group, carbonyl
Base, carboxylic acid group, ester group, isonitrile base, sulfenyl, sulfinyl, sulfonyl, phosphino- and a combination thereof,
Condition is that the compound is not following compound:
2. compound according to claim 1, wherein X is S.
3. compound according to claim 1, wherein X1To X8At least one of be N.
4. compound according to claim 1, wherein Z1、Z3、Z4、Z5、Z6、Z7And Z8At least one of be N.
5. compound according to claim 1, wherein A is selected from the group being made up of:
6. compound according to claim 1, wherein B is selected from the group being made up of:
7. compound according to claim 1, wherein M is selected from the group being made up of:
8. compound according to claim 1, wherein D is selected from the group being made up of:
9. compound according to claim 1, wherein the compound is selected from the group being made up of:
10. a kind of device, it includes one or more organic light emitting apparatus, in one or more described organic light emitting apparatus at least one
Person includes:
Anode；
Cathode；With
The organic layer being placed between the anode and the cathode, it includes any claims according to claim 1-9
The compound.
11. device according to claim 10, wherein the organic layer is emission layer, and according to claim 1 in -9
Compound described in any claim is main body.
12. device according to claim 10 further includes phosphorescent emissions dopant, wherein the phosphorescent emissions are mixed
Miscellaneous dose be a part with the ligand at least one ligand or when the ligand is more than bidentate transition
Metal complex, the ligand are selected from the group being made up of:
Wherein Ra、Rb、RcAnd RdIt can indicate monosubstituted base, disubstituted, three substituent groups or four substituent groups or unsubstituted；
Wherein Ra、Rb、RcAnd RdIndependently selected from the group being made up of: hydrogen, deuterium, halogen, alkyl, naphthenic base, miscellaneous alkyl, virtue
Alkyl, alkoxy, aryloxy group, amino, silylation, alkenyl, cycloalkenyl, miscellaneous thiazolinyl, alkynyl, aryl, heteroaryl, acyl group, carbonyl,
Carboxylic acid group, ester group, itrile group, isonitrile base, sulfenyl, sulfinyl, sulfonyl, phosphino- and a combination thereof；And
Wherein Ra、Rb、RcAnd RdIn two adjacent substituents optionally engage with formed fused rings or formed multidentate ligand.
13. a kind of composite, it includes compounds described in any claim according to claim 1-9.
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| WO2016143589A1 (en) | 2015-03-09 | 2016-09-15 | 保土谷化学工業株式会社 | Light emitting material and organic electroluminescent element |
| US11818949B2 (en) | 2015-04-06 | 2023-11-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10593890B2 (en) | 2015-04-06 | 2020-03-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11495749B2 (en) | 2015-04-06 | 2022-11-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| JP6788314B2 (en) * | 2016-01-06 | 2020-11-25 | コニカミノルタ株式会社 | Organic electroluminescence element, manufacturing method of organic electroluminescence element, display device and lighting device |
| KR102488916B1 (en) * | 2016-05-06 | 2023-01-18 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | Light-emitting element, display device, electronic device, and lighting device |
| US11834459B2 (en) | 2018-12-12 | 2023-12-05 | Universal Display Corporation | Host materials for electroluminescent devices |
| US11758807B2 (en) | 2019-02-22 | 2023-09-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN109912610B (en) * | 2019-04-04 | 2020-06-23 | 石家庄诚志永华显示材料有限公司 | Organic compound and application thereof in preparation of organic electroluminescent element |
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| KR101324788B1 (en) * | 2009-12-31 | 2013-10-31 | (주)씨에스엘쏠라 | Organic light device and organic light compound for the same |
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