CN106928223A - Compound, organic light emitting apparatus and display device including the compound - Google Patents

Compound, organic light emitting apparatus and display device including the compound Download PDF

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CN106928223A
CN106928223A CN201611243743.7A CN201611243743A CN106928223A CN 106928223 A CN106928223 A CN 106928223A CN 201611243743 A CN201611243743 A CN 201611243743A CN 106928223 A CN106928223 A CN 106928223A
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朴俊河
李银永
金荣国
沈文基
李孝荣
郑恩在
黄晳焕
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Samsung Display Co Ltd
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Samsung Display Co Ltd
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Abstract

A kind of compound, organic light emitting apparatus and display device including the compound represented by formula 1：<Formula 1>Wherein formula 1 is identical with described in text.

Description

Compound, organic light emitting apparatus and display device including the compound
Cross-Reference to Related Applications
This application claims special to the South Korea that Korean Intellectual Property Office submits on December 29th, 2015 and on November 8th, 2016 The rights and interests of profit application No. 10-2015-0188905 and No. 10-2016-0148192, the disclosure of the application is by quoting It is hereby incorporated by reference in its entirety.
Technical field
One or more implementation methods are related to compound and the organic light emitting apparatus including the compound.
Background technology
Organic light emitting apparatus to produce full-colour image, also with wide viewing angle, high-contrast, short response time and excellent The selfluminous device of brightness, driving voltage and response speed characteristic.
The example of such organic light emitting apparatus may include the first electrode set on substrate, and be set in sequence in the Hole transport area, luminescent layer, electric transmission area and second electrode on one electrode.The hole provided by first electrode may pass through sky Cave transmission range is moved to luminescent layer, and the electronics provided from second electrode may pass through electric transmission area and be moved to luminescent layer.Carry Stream (such as hole and electronics) is combined to produce exciton in luminescent layer.These excitons transit to ground state from excitation state, thus Produce light.
The content of the invention
One or more implementation methods include being suitable as with excellent electron transport ability and stability of material The compound of electron injection material or electron transport material, and have by using the compound high efficiency, low-voltage, High brightness and long-life organic light emitting apparatus.
Other aspect explains part in the following description, and part will be obvious from the description, or Can be known by implementing presented implementation method.
According to one or more implementation methods, formula 1 is represented：
<Formula 1>
In formula 1,
R1And R2Hydrogen, deuterium, halogen, nitro, cyano group, substituted or unsubstituted C can be each independently selected from1-C60Alkyl, take Generation or unsubstituted C2-C60Alkenyl, substituted or unsubstituted C2-C60Alkynyl, substituted or unsubstituted C1-C60Alkoxy, substitution Or unsubstituted C3-C10Cycloalkyl, substituted or unsubstituted C1-C10Heterocyclylalkyl, substituted or unsubstituted C3-C10Cycloalkenyl group, Substituted or unsubstituted C1-C10Heterocycloalkenyl, substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C6-C60Fragrant oxygen Base, substituted or unsubstituted C6-C60Arylthio, substituted or unsubstituted C1-C60Heteroaryl, it is substituted or unsubstituted unit price it is non- Aromatic condensed polycyclic group, substituted or unsubstituted the non-aromatic of unit price condense miscellaneous polycyclic moiety ,-P (=O) R3R4,-P (=S) R5R6,-S (=O)2R7With-S (=O) R8R9,
X1To X8CR can be each independently selected from11And N,
Selected from X1To X8At least one of can be N,
R3To R9And R11Substituted or unsubstituted C can be each independently selected from1-C60Alkyl, substituted or unsubstituted C3-C10 Cycloalkyl, substituted or unsubstituted C1-C10Heterocyclylalkyl, substituted or unsubstituted C6-C60Aryl and substituted or unsubstituted C1- C60Heteroaryl,
L1And L2Substituted or unsubstituted C can be each independently selected from6-C60Arlydene, substituted or unsubstituted C1-C60It is sub- Heteroaryl, the non-aromatic fused polycycle group of substituted or unsubstituted divalence and the non-aromatic of substituted or unsubstituted divalence are condensed Miscellaneous polycyclic moiety,
A to d can be each independently 0 to 3 integer,
Selected from the C of substitution1-C60Alkyl, the C of substitution2-C60Alkenyl, the C of substitution2-C60Alkynyl, the C of substitution1-C60Alcoxyl Base, the C of substitution3-C10Cycloalkyl, the C of substitution1-C10Heterocyclylalkyl, the C of substitution3-C10Cycloalkenyl group, the C of substitution1-C10Heterocycle alkene Base, the C of substitution6-C60Aryl, the C of substitution6-C60Aryloxy group, the C of substitution6-C60Arylthio, the C of substitution1-C60Heteroaryl, substitution Univalent non-aromatic fused polycycle group, the univalent non-aromatic of substitution condense miscellaneous polycyclic moiety, the C of substitution6-C60Sub- virtue Base, the C of substitution1-C60Inferior heteroaryl, the non-aromatic fused polycycle group of the divalence of substitution and the non-aromatic of substituted divalence are condensed At least one of substitution base of miscellaneous polycyclic moiety substitution base may be selected from：
Deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amino, amidino groups, diazanyl, hydrazone group, carboxylic acid group or its salt, sulfonic acid Base or its salt, phosphate or its salt, C1-C60Alkyl, C2-C60Alkenyl, C2-C60Alkynyl and C1-C60Alkoxy；
Each it is selected from the C of at least one of the following substitution1-C60Alkyl, C2-C60Alkenyl, C2-C60Alkynyl and C1-C60 Alkoxy：Deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amino, amidino groups, diazanyl, hydrazone group, carboxylic acid group or its salt, sulfonic acid Base or its salt, phosphate or its salt, C3-C10Cycloalkyl, C1-C10Heterocyclylalkyl, C3-C10Cycloalkenyl group, C1-C10Heterocycloalkenyl, C6- C60Aryl, C6-C60Aryloxy group, C6-C60Arylthio, C1-C60Heteroaryl, unit price non-aromatic fused polycycle group, unit price it is non- Aromatics condenses miscellaneous polycyclic moiety ,-N (Q11)(Q12)、-Si(Q13)(Q14)(Q15) and-B (Q16)(Q17)；
C3-C10Cycloalkyl, C1-C10Heterocyclylalkyl, C3-C10Cycloalkenyl group, C1-C10Heterocycloalkenyl, C6-C60Aryl, C6-C60Virtue Epoxide, C6-C60Arylthio, C1-C60Heteroaryl, unit price non-aromatic fused polycycle group and unit price it is non-aromatic condense it is miscellaneous polycyclic Group；And
Each it is selected from the C of at least one of the following substitution3-C10Cycloalkyl, C1-C10Heterocyclylalkyl, C3-C10Cyclenes Base, C1-C10Heterocycloalkenyl, C6-C60Aryl, C6-C60Aryloxy group, C6-C60Arylthio, C1-C60Heteroaryl, unit price it is non-aromatic thick Close polycyclic moiety and the non-aromatic of unit price condenses miscellaneous polycyclic moiety：Deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amino, Amidino groups, diazanyl, hydrazone group, carboxylic acid group or its salt, sulfonic group or its salt, phosphate or its salt, C1-C60Alkyl, C2-C60Alkenyl, C2- C60Alkynyl, C1-C60Alkoxy, C3-C10Cycloalkyl, C1-C10Heterocyclylalkyl, C3-C10Cycloalkenyl group, C1-C10Heterocycloalkenyl, C6-C60 Aryl, C6-C60Aryloxy group, C6-C60Arylthio, C1-C60Heteroaryl, unit price non-aromatic fused polycycle group, unit price it is non-aromatic Race condenses miscellaneous polycyclic moiety ,-N (Q21)(Q22)、-Si(Q23)(Q24)(Q25) and-B (Q26)(Q27), and
Q11To Q17And Q21To Q27Hydrogen, deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, ammonia can be each independently selected from Base, amidino groups, diazanyl, hydrazone group, carboxylic acid group or its salt, sulfonic group or its salt, phosphate or its salt, C1-C60Alkyl, C2-C60Alkenyl, C2-C60Alkynyl, C1-C60Alkoxy, C3-C10Cycloalkyl, C1-C10Heterocyclylalkyl, C3-C10Cycloalkenyl group, C1-C10Heterocycloalkenyl, C6- C60Aryl, C1-C60Heteroaryl, the non-aromatic fused polycycle group of unit price and the non-aromatic of unit price condense miscellaneous polycyclic moiety.
According to one or more implementation methods, organic light emitting apparatus include：First electrode；Towards the second electricity of first electrode Pole；And organic layer between the first electrode and the second electrode, organic layer include luminescent layer, wherein organic layer may include above-mentioned Compound.
According to one or more implementation methods, flat panel display equipment includes the organic light emitting apparatus, wherein organic light emission The first electrode of device can be electrically connected with the source electrode of thin film transistor (TFT) or drain electrode.
Brief description of the drawings
With reference to accompanying drawing, from the following description of implementation method, these and/or other aspect will be clear and be easier reason Solution, in the accompanying drawings：
Fig. 1 is the schematic diagram of the organic light emitting apparatus according to implementation method；
Fig. 2 is the schematic diagram of the organic light emitting apparatus according to implementation method；
Fig. 3 is the schematic diagram of the organic light emitting apparatus according to implementation method；And
Fig. 4 is the schematic diagram of the organic light emitting apparatus according to implementation method.
Specific embodiment
Compound according to implementation method is represented by following formula 1：
<Formula 1>
In formula 1,
R1And R2Hydrogen, deuterium, halogen, nitro, cyano group, substituted or unsubstituted C can be each independently selected from1-C60Alkyl, take Generation or unsubstituted C2-C60Alkenyl, substituted or unsubstituted C2-C60Alkynyl, substituted or unsubstituted C1-C60Alkoxy, substitution Or unsubstituted C3-C10Cycloalkyl, substituted or unsubstituted C1-C10Heterocyclylalkyl, substituted or unsubstituted C3-C10Cycloalkenyl group, Substituted or unsubstituted C1-C10Heterocycloalkenyl, substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C6-C60Fragrant oxygen Base, substituted or unsubstituted C6-C60Arylthio, substituted or unsubstituted C1-C60Heteroaryl, it is substituted or unsubstituted unit price it is non- Aromatic condensed polycyclic group, substituted or unsubstituted the non-aromatic of unit price condense miscellaneous polycyclic moiety ,-P (=O) R3R4,-P (=S) R5R6,-S (=O)2R7With-S (=O) R8R9,
X1To X8CR can be each independently selected from11And N,
Selected from X1To X8At least one of can be N,
R3To R9And R11Substituted or unsubstituted C can be each independently selected from1-C60Alkyl, substituted or unsubstituted C3-C10 Cycloalkyl, substituted or unsubstituted C1-C10Heterocyclylalkyl, substituted or unsubstituted C6-C60Aryl and substituted or unsubstituted C1- C60Heteroaryl,
L1And L2Substituted or unsubstituted C can be each independently selected from6-C60Arlydene, substituted or unsubstituted C1-C60It is sub- Heteroaryl, the non-aromatic fused polycycle group of substituted or unsubstituted divalence and the non-aromatic of substituted or unsubstituted divalence are condensed Miscellaneous polycyclic moiety,
A to d can be each independently 0 to 3 integer,
Selected from the C of substitution1-C60Alkyl, the C of substitution2-C60Alkenyl, the C of substitution2-C60Alkynyl, the C of substitution1-C60Alcoxyl Base, the C of substitution3-C10Cycloalkyl, the C of substitution1-C10Heterocyclylalkyl, the C of substitution3-C10Cycloalkenyl group, the C of substitution1-C10Heterocycle alkene Base, the C of substitution6-C60Aryl, the C of substitution6-C60Aryloxy group, the C of substitution6-C60Arylthio, the C of substitution1-C60Heteroaryl, substitution Univalent non-aromatic fused polycycle group, the univalent non-aromatic of substitution condense miscellaneous polycyclic moiety, the C of substitution6-C60Sub- virtue Base, the C of substitution1-C60Inferior heteroaryl, the non-aromatic fused polycycle group of the divalence of substitution and the non-aromatic of substituted divalence are condensed At least one of substitution base of miscellaneous polycyclic moiety substitution base may be selected from：
Deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amino, amidino groups, diazanyl, hydrazone group, carboxylic acid group or its salt, sulfonic acid Base or its salt, phosphate or its salt, C1-C60Alkyl, C2-C60Alkenyl, C2-C60Alkynyl and C1-C60Alkoxy；
Each it is selected from the C of at least one of the following substitution1-C60Alkyl, C2-C60Alkenyl, C2-C60Alkynyl and C1-C60 Alkoxy：Deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amino, amidino groups, diazanyl, hydrazone group, carboxylic acid group or its salt, sulfonic acid Base or its salt, phosphate or its salt, C3-C10Cycloalkyl, C1-C10Heterocyclylalkyl, C3-C10Cycloalkenyl group, C1-C10Heterocycloalkenyl, C6- C60Aryl, C6-C60Aryloxy group, C6-C60Arylthio, C1-C60Heteroaryl, unit price non-aromatic fused polycycle group, unit price it is non- Aromatics condenses miscellaneous polycyclic moiety ,-N (Q11)(Q12)、-Si(Q13)(Q14)(Q15) and-B (Q16)(Q17)；
C3-C10Cycloalkyl, C1-C10Heterocyclylalkyl, C3-C10Cycloalkenyl group, C1-C10Heterocycloalkenyl, C6-C60Aryl, C6-C60Virtue Epoxide, C6-C60Arylthio, C1-C60Heteroaryl, unit price non-aromatic fused polycycle group and unit price it is non-aromatic condense it is miscellaneous polycyclic Group；And
Each it is selected from the C of at least one of the following substitution3-C10Cycloalkyl, C1-C10Heterocyclylalkyl, C3-C10Cyclenes Base, C1-C10Heterocycloalkenyl, C6-C60Aryl, C6-C60Aryloxy group, C6-C60Arylthio, C1-C60Heteroaryl, unit price it is non-aromatic thick Close polycyclic moiety and the non-aromatic of unit price condenses miscellaneous polycyclic moiety：Deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amino, Amidino groups, diazanyl, hydrazone group, carboxylic acid group or its salt, sulfonic group or its salt, phosphate or its salt, C1-C60Alkyl, C2-C60Alkenyl, C2- C60Alkynyl, C1-C60Alkoxy, C3-C10Cycloalkyl, C1-C10Heterocyclylalkyl, C3-C10Cycloalkenyl group, C1-C10Heterocycloalkenyl, C6-C60 Aryl, C6-C60Aryloxy group, C6-C60Arylthio, C1-C60Heteroaryl, unit price non-aromatic fused polycycle group, unit price it is non-aromatic Race condenses miscellaneous polycyclic moiety ,-N (Q21)(Q22)、-Si(Q23)(Q24)(Q25) and-B (Q26)(Q27), and
Q11To Q17And Q21To Q27Hydrogen, deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, ammonia can be each independently selected from Base, amidino groups, diazanyl, hydrazone group, carboxylic acid group or its salt, sulfonic group or its salt, phosphate or its salt, C1-C60Alkyl, C2-C60Alkenyl, C2-C60Alkynyl, C1-C60Alkoxy, C3-C10Cycloalkyl, C1-C10Heterocyclylalkyl, C3-C10Cycloalkenyl group, C1-C10Heterocycloalkenyl, C6- C60Aryl, C1-C60Heteroaryl, the non-aromatic fused polycycle group of unit price and the non-aromatic of unit price condense miscellaneous polycyclic moiety.
Work as X1To X8It is each independently selected from CR11With N and have selected multiple CR11When, R11Can be same to each other or different to each other.
The example of electron transport material may include metal-organic complex, and the metal-organic complex is organic supramolecular Material, and with relatively excellent stability and relatively excellent electric transmission speed on electronics.It has been reported that having In organic metal complex, the Alq with excellent stability and electron affinity high3It is most excellent.However, when in blue-light-emitting Alq is used in device3When, due to colour purity can be reduced by being lighted caused by exciton diffusion.Additionally, flavones (flavon) is derivative Thing or germanium and silicon cyclopentadiene derivant are known.
The example of organic supramolecular material may include 2- biphenyl -4- bases -5- (the 4- tert-butyl benzenes being connected with spiro-compound Base) -1,3,4- oxadiazoles (PBD) derivative and have the 2 of hole blocking ability and excellent electron transport ability simultaneously, 2', 2 "-(bases of benzene -1,3,5- three)-three (1- phenyl -1H- benzimidazoles) (TPBI).Especially, it is commonly known that benzimidazole spreads out Biology has excellent durability.
However, the physically or chemically change in due to organic material, the photochemistry in organic material or electrochemical change, the moon The oxidation of pole, peeling and lack durability, thus using organic supramolecular material as electron transfer layer organic light emission Device has short luminescent lifetime and low preservation durability and reliability.
In order to overcome the above to limit to, the disclosure provides a kind of compound including new type heterocycle and uses includes describedization The organic light emitting apparatus of the organic layer of compound.Compound according to one or more implementation methods, including new type heterocycle be with Excellent electrical characteristics, charge transport ability high and luminous power, with high glass-transition temperature and it is prevented from the material of crystallization Material.The compound can be used as be suitable for the fluorescent apparatus of all colours (such as red, green, blueness, white etc.) with The electron transport material of phosphorescent devices.By using the compound, can manufacture with high efficiency, low-voltage, high brightness and length The organic light emitting apparatus in life-span.
In one or more implementation methods, the R in formula 111Can be hydrogen or deuterium.
In one or more implementation methods, a and b in formula 1 can be each independently 0 to 2 integer.For example, a and b 0 or 1 can be each independently.
In one or more implementation methods, the L in formula 11And L2Can be each independently selected from by formula 2a to 2f The compound of expression derives the group for obtaining：
L1And L2Can be each independently divalence or trivalent linking group, and at the position of hydrogen in formula 2a to 2f Key can be formed.
In one or more implementation methods, the R in formula 11And R2Can be by selected from an expression in formula 3a to 3j：
In formula 3a to 3j,
X can be O or S,
H1Can be CR21R22、NR23, O or S,
R21To R23And Z1Hydrogen, deuterium, halogen, cyano group, nitro, hydroxyl, carboxyl, substitution or unsubstituted can be each independently selected from C1-C20Alkyl, substituted or unsubstituted C6-C20Aryl, substituted or unsubstituted C1-C20It is heteroaryl, substituted or unsubstituted The non-aromatic fused polycycle group of unit price and substituted or unsubstituted the non-aromatic of unit price condense miscellaneous polycyclic moiety,
Work as Z1Quantity be more than or equal to 2 when, two or more Z1Can be same to each other or different to each other,
P in formula 3a can be 1 to 5 integer,
P in formula 3b can be 1 to 4 integer,
P in formula 3c can be 1 to 4 integer,
P in formula 3d can be 1 to 9 integer,
P in formula 3f can be 1 to 6 integer,
P in formula 3g can be 1 to 7 integer,
P in formula 3h can be 1 to 8 integer,
P in formula 3i can be 1 to 6 integer,
P in formula 3j can be 1 to 7 integer, and
* the binding site with adjacent atom is represented.
In one or more implementation methods, formula 1 can be represented by formula 2：
<Formula 2>
In one or more implementation methods, formula 1 can be represented by formula 3：
<Formula 3>
The definition of substitution base and symbol in formula 2 to 3 is identical with as described above.
In one or more implementation methods, the compound of formula 1 can be selected from compound 1 to 99 in one, but this Disclosed embodiment not limited to this：
[description of Fig. 1]
Fig. 1 is the schematic diagram of the organic light emitting apparatus 10 according to implementation method.Organic light emitting apparatus 10 include first electrode 110th, organic layer 150 and second electrode 190.
Below with reference to Fig. 1 descriptions are according to the structure of the organic light emitting apparatus 10 of implementation method and prepare organic light emission dress The method for putting 10.
[first electrode 110]
In Fig. 1, substrate can be additionally provided under first electrode 110 or on second electrode 190.Substrate can be Glass substrate or plastic base, each with excellent mechanical strength, heat endurance, transparency, surface flatness, ease for operation And water proofing property.
First electrode 110 can be formed by depositing or sputtering on substrate for forming the material of first electrode 110.When When first electrode 110 is anode, the material for first electrode may be selected from the material with high work content in order to hole injection.
First electrode 110 can be reflecting electrode, half transmitting electrode or transmission electrode.When first electrode 110 is transmission electrode When, the material for forming first electrode may be selected from tin indium oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), oxidation Zinc (ZnO) and its any combination, but embodiment of the present disclosure not limited to this.In one or more implementation methods, when When one electrode 110 is half transmitting electrode or reflecting electrode, the material for forming first electrode may be selected from magnesium (Mg), silver-colored (Ag), Aluminium (Al), aluminium-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and its any combination.However, the disclosure Implementation method not limited to this.
First electrode 110 can have single layer structure or the sandwich construction including two or more.For example, first electrode 110 three-deckers can with ITO/Ag/ITO, but the structure not limited to this of first electrode 110.
[organic layer 150]
Organic layer 150 is arranged in first electrode 110.Organic layer 150 may include luminescent layer.
Organic layer 150 can further include hole transport area and electric transmission area, wherein the hole transport area is first Between electrode 110 and luminescent layer, and the electric transmission area is between luminescent layer and second electrode 190.
[the hole transport area in organic layer 150]
Hole transport area can have i) single layer structure, ii including single layer (including single material)) include single layer (bag Include various different materials) single layer structure or iii) have include the sandwich construction of multiple layers of various different materials.
Hole transport area may include selected from hole injection layer (HIL), hole transmission layer (HTL), luminous auxiliary layer and electronics At least one of barrier layer (EBL) layer.
For example, hole transport area can have single layer structure or sandwich construction, the single layer structure includes that single layer is (including more Plant different materials), the sandwich construction has hole injection layer/hole transport Rotating fields, hole injection layer/hole transport Layer/luminous auxiliary Rotating fields, hole injection layer/luminous auxiliary Rotating fields, hole transmission layer/luminous auxiliary Rotating fields or hole note Enter layer/hole transmission layer/electron barrier layer structure, wherein for every kind of structure, constituting layer with the order of above-mentioned regulation from first Electrode 110 is stacked gradually, but the structure not limited to this in hole transport area.
Hole transport area may include selected from m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiral shell-TPD, Spiral shell-NPB, NPB, TAPC, HMTPD, 4,4' for methylating, 4 "-three (N- carbazyls) triphenylamine (TCTA), polyaniline/12 Alkyl benzene sulphonate (PANI/DBSA), poly- (3,4- ethylenedioxy thiophenes/poly- (4- styrene sulfonates) (PEDOT/PSS), polyphenyl Amine/camphorsulfonic acid (PANI/CSA), polyaniline/poly- (4- styrene sulfonates) (PANI/PSS), the compound represented by formula 201 With at least one in the compound represented by formula 202：
<Formula 201>
<Formula 202>
In formula 201 and 202,
L201To L204Substituted or unsubstituted C can be each independently selected from3-C10Cycloalkylidene, substituted or unsubstituted C1- C10Sub- Heterocyclylalkyl, substituted or unsubstituted C3-C10Sub- cycloalkenyl group, substituted or unsubstituted C1-C10Sub- heterocycloalkenyl, substitution or Unsubstituted C6-C60Arlydene, substituted or unsubstituted C1-C60Inferior heteroaryl, substituted or unsubstituted divalence it is non-aromatic thick Close polycyclic moiety and the non-aromatic of substituted or unsubstituted divalence condenses miscellaneous polycyclic moiety；
L205May be selected from *-O-*', *-S-*', *-N (Q201)-* ', substituted or unsubstituted C1-C20Alkylidene, substitution or not Substituted C2-C20Alkenylene, substituted or unsubstituted C3-C10Cycloalkylidene, substituted or unsubstituted C1-C10Sub- Heterocyclylalkyl, Substituted or unsubstituted C3-C10Sub- cycloalkenyl group, substituted or unsubstituted C1-C10Sub- heterocycloalkenyl, substituted or unsubstituted C6-C60 Arlydene, substituted or unsubstituted C1-C60Inferior heteroaryl, the non-aromatic fused polycycle group of substituted or unsubstituted divalence and take Generation or the non-aromatic of unsubstituted divalence condense miscellaneous polycyclic moiety,
Xa1 to xa4 can be each independently 0 to 3 integer,
Xa5 can be 1 to 10 integer,
R201To R204And Q201Substituted or unsubstituted C can be each independently selected from3-C10It is cycloalkyl, substituted or unsubstituted C1-C10Heterocyclylalkyl, substituted or unsubstituted C3-C10Cycloalkenyl group, substituted or unsubstituted C1-C10Heterocycloalkenyl, substitution or not Substituted C6-C60Aryl, substituted or unsubstituted C6-C60Aryloxy group, substituted or unsubstituted C6-C60Arylthio, substitution or not Substituted C1-C60The non-aromatic fused polycycle group and substituted or unsubstituted unit price of heteroaryl, substituted or unsubstituted unit price Non-aromatic condense miscellaneous polycyclic moiety.
In one or more implementation methods, in formula 202, R201And R202Optionally pass through singly-bound, dimethyl-methylene Base or diphenyl-methylene are connected, and R203And R204Optionally pass through singly-bound, dimethyl-methylene or diphenyl-methylene Base is connected.
In one or more implementation methods, in formula 201 and 202,
L201To L205Can be each independently selected from：
Phenylene, sub- pentalene base, sub-indenyl, naphthylene, sub- azulenyl, sub- heptalene base, sub- indacene base, sub- acenaphthenyl, Fluorenylidene, the sub- fluorenyl of spiral shell-two, sub- benzo fluorenyl, sub- dibenzo fluorenyl, that alkenyl of Asia and Africa, phenanthrylene, anthrylene, sub- fluoranthene base, It is sub- benzo phenanthryl, sub- pyrenyl, sub- base in the wrong, sub- aphthacene base, sub- Pi base, sub- perylene base, sub- pentaphene base, sub- hexacene base, sub- and five Phenyl, sub- rubicene base, sub- cool base, sub- ovalene base, sub- thienyl, furylidene, sub- carbazyl, sub- indyl, sub- iso-indoles Base, sub- benzofuranyl, sub- benzothienyl, sub- dibenzofuran group, sub- dibenzothiophenes base, sub- benzo carbazole base, sub- two Benzo carbazole base, sub- dibenzo Silole base and sub- pyridine radicals；And
Each it is selected from phenylene, sub- pentalene base, sub-indenyl, naphthylene, the sub- Azulene of at least one of the following substitution Base, sub- heptalene base, sub- indacene base, sub- acenaphthenyl, fluorenylidene, the sub- fluorenyl of spiral shell-two, sub- benzo fluorenyl, sub- dibenzo fluorenyl, Asia Non- that alkenyl, phenanthrylene, anthrylene, sub- fluoranthene base, sub- benzo phenanthryl, sub- pyrenyl, sub- base in the wrong, sub- aphthacene base, sub- Pi base, Asia Perylene base, sub- pentaphene base, sub- hexacene base, sub- pentacene base, sub- rubicene base, sub- cool base, sub- ovalene base, sub- thienyl, sub- furan Mutter base, sub- carbazyl, sub- indyl, sub- isoindolyl, sub- benzofuranyl, sub- benzothienyl, sub- dibenzofuran group, Asia Dibenzothiophenes base, sub- benzo carbazole base, sub- dibenzo-carbazole base, sub- dibenzo Silole base and sub- pyridine radicals： Deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C1-C20Alkyl, C1-C20Alkoxy, cyclopenta, Cyclohexyl, suberyl, cyclopentenyl, cyclohexenyl group, phenyl, xenyl, terphenyl, by C1-C10Alkyl-substituted phenyl, By-F substitution phenyl, pentalene base, indenyl, naphthyl, azulenyl, heptalene base, indacene base, acenaphthenyl, fluorenyl, the fluorenyl of spiral shell-two, Benzo fluorenyl, dibenzo fluorenyl, non-that alkenyl, phenanthryl, anthryl, fluoranthene base, benzo phenanthryl, pyrenyl, Qu Ji, aphthacene base, Pi Ji, perylenes base, pentaphene base, hexacene base, pentacene base, rubicene base, cool base, ovalene base, thienyl, furyl, carbazyl, Yin Diindyl base, isoindolyl, benzofuranyl, benzothienyl, dibenzofuran group, dibenzothiophenes base, benzo carbazole base, hexichol And carbazyl, dibenzo Silole base, pyridine radicals ,-Si (Q31)(Q32)(Q33) and-N (Q31)(Q32),
Wherein Q31To Q33C can be each independently selected from1-C10Alkyl, C1-C10Alkoxy, phenyl, xenyl, terphenyl And naphthyl.
In one or more implementation methods, xa1 to xa4 can be each independently 0,1 or 2.
In one or more implementation methods, xa5 can be 1,2,3 or 4.
In one or more implementation methods, R201To R204And Q201Phenyl, xenyl, three can be each independently selected from Phenyl, pentalene base, indenyl, naphthyl, azulenyl, heptalene base, indacene base, acenaphthenyl, fluorenyl, the fluorenyl of spiral shell-two, benzo fluorenyl, Dibenzo fluorenyl, non-that alkenyl, phenanthryl, anthryl, fluoranthene base, benzo phenanthryl, pyrenyl, Qu Ji, aphthacene base, Pi base, perylene base, penta Fen Ji, hexacene base, pentacene base, rubicene base, cool base, ovalene base, thienyl, furyl, carbazyl, indyl, different Yin Diindyl base, benzofuranyl, benzothienyl, dibenzofuran group, dibenzothiophenes base, benzo carbazole base, dibenzo-carbazole base, Dibenzo Silole base and pyridine radicals；And
Each it is selected from phenyl, xenyl, terphenyl, pentalene base, indenyl, the naphthalene of at least one of the following substitution Base, azulenyl, heptalene base, indacene base, acenaphthenyl, fluorenyl, the fluorenyl of spiral shell-two, benzo fluorenyl, dibenzo fluorenyl, non-that alkenyl, phenanthrene Base, anthryl, fluoranthene base, benzo phenanthryl, pyrenyl, Qu Ji, aphthacene base, Pi base, perylene base, pentaphene base, hexacene base, pentacene Base, rubicene base, cool base, ovalene base, thienyl, furyl, carbazyl, indyl, isoindolyl, benzofuranyl, benzo Thienyl, dibenzofuran group, dibenzothiophenes base, benzo carbazole base, dibenzo-carbazole base, dibenzo Silole base And pyridine radicals：Deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C1-C20Alkyl, C1-C20Alcoxyl Base, cyclopenta, cyclohexyl, suberyl, cyclopentenyl, cyclohexenyl group, phenyl, xenyl, terphenyl, by C1-C10Alkyl takes The phenyl in generation, by the phenyl of-F substitutions, pentalene base, indenyl, naphthyl, azulenyl, heptalene base, indacene base, acenaphthenyl, fluorenyl, The fluorenyl of spiral shell-two, benzo fluorenyl, dibenzo fluorenyl, non-that alkenyl, phenanthryl, anthryl, fluoranthene base, benzo phenanthryl, pyrenyl, Qu Ji and Tetraphenyl, Pi Ji, perylenes base, pentaphene base, hexacene base, pentacene base, rubicene base, cool base, ovalene base, thienyl, furyl, Carbazyl, indyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuran group, dibenzothiophenes base, benzo click Oxazolyl, dibenzo-carbazole base, dibenzo Silole base, pyridine radicals ,-Si (Q31)(Q32)(Q33) and-N (Q31)(Q32),
Wherein Q31To Q33Can be identical with described above.
In one or more implementation methods, in formula 201, R201To R203At least one of can select independently of one another From：
Fluorenyl, the fluorenyl of spiral shell-two, carbazyl, dibenzofuran group and dibenzothiophenes base；And
Each be selected from least one of the following substitution fluorenyl, the fluorenyl of spiral shell-two, carbazyl, dibenzofuran group and Dibenzothiophenes base：Deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C1-C20Alkyl, C1-C20Alkane Epoxide, cyclopenta, cyclohexyl, suberyl, cyclopentenyl, cyclohexenyl group, phenyl, xenyl, terphenyl, by C1-C10Alkyl Substituted phenyl, by the phenyl of-F substitutions, naphthyl, fluorenyl, the fluorenyl of spiral shell-two, carbazyl, dibenzofuran group and dibenzothiophenes Base, but embodiment of the present disclosure not limited to this.
In one or more implementation methods, in formula 202, i) R201And R202Can be connected by singly-bound and/or ii) R203 And R204Can be connected by singly-bound.
In one or more implementation methods, in formula 202, R201To R204At least one of may be selected from：
Carbazyl；And
It is selected from the substituted carbazyl of following at least one：Deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidine Base, diazanyl, hydrazone group, C1-C20Alkyl, C1-C20Alkoxy, cyclopenta, cyclohexyl, suberyl, cyclopentenyl, cyclohexenyl group, benzene Base, xenyl, terphenyl, by C1-C10Alkyl-substituted phenyl, quilt-F substitution phenyl, naphthyl, fluorenyl, the fluorenyl of spiral shell-two, Carbazyl, dibenzofuran group and dibenzothiophenes base, but embodiment of the present disclosure not limited to this.
The compound represented by formula 201 can be represented by formula 201A：
<Formula 201A>
In one or more implementation methods, the compound represented by formula 201 can be represented by following formula 201A (1), but It is embodiment of the present disclosure not limited to this：
<Formula 201A (1)>
In one or more implementation methods, the compound represented by formula 201 can be represented by following formula 201A-1, but Embodiment of the present disclosure not limited to this：
<Formula 201A-1>
In one or more implementation methods, the compound represented by formula 202 can be represented by formula 202A：
<Formula 202A>
In one or more implementation methods, the compound represented by formula 202 can be represented by formula 202A-1：
<Formula 202A-1>
In formula 201A, 201A (1), 201A-1,202A and 202A-1,
L201To L203, xa1 to xa3, xa5 and R202To R204Can be identical with as described above,
R211And R212Can with R203Described is identical,
R213To R217Can be each independently selected from hydrogen, deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, Hydrazone group, C1-C20Alkyl, C1-C20Alkoxy, cyclopenta, cyclohexyl, suberyl, cyclopentenyl, cyclohexenyl group, phenyl, biphenyl Base, terphenyl, by C1-C10Alkyl-substituted phenyl, the phenyl of quilt-F substitutions, pentalene base, indenyl, naphthyl, azulenyl, heptan take Alkenyl, indacene base, acenaphthenyl, fluorenyl, the fluorenyl of spiral shell-two, benzo fluorenyl, dibenzo fluorenyl, non-that alkenyl, phenanthryl, anthryl, fluoranthene It is base, benzo phenanthryl, pyrenyl, Qu Ji, aphthacene base, Pi base, perylene base, pentaphene base, hexacene base, pentacene base, rubicene base, cool Base, ovalene base, thienyl, furyl, carbazyl, indyl, isoindolyl, benzofuranyl, benzothienyl, dibenzo furan Mutter base, dibenzothiophenes base, benzo carbazole base, dibenzo-carbazole base, dibenzo Silole base and pyridine radicals.
Hole transport area may include the compound selected from compound HT1 to HT39, but embodiment of the present disclosure is not limited In this：
The thickness in hole transport area can be aboutTo aboutFor example, aboutTo aboutModel In enclosing.When hole transport area includes at least one of hole injection layer and hole transmission layer, the thickness of hole injection layer can AboutTo aboutFor example, aboutTo aboutIn the range of, and the thickness of hole transmission layer can AboutTo aboutFor example, aboutTo aboutIn the range of.When hole transport area, hole injection layer During with the thickness of hole transmission layer in the range of these, gratifying hole can be obtained in the case where driving voltage is not dramatically increased Transmission characteristic.
Luminous auxiliary layer can increase luminous by according to the wavelength compensation optical resonance distance of the light launched by luminescent layer Efficiency, and electronic barrier layer can stop the flowing of the electronics from electric transmission area.Luminous auxiliary layer and electronic barrier layer can Including above-mentioned material.
[P- dopants]
In addition to these materials, hole transport area can further include to produce material for the electric charge for improving electric conductivity Material.Charge generating material can be uniformly or non-uniformly scattered in hole transport area.
Charge generating material can be such as p-doping agent.
In one or more implementation methods, the lowest unocccupied molecular orbital (LUMO) of p-doping agent can for -3.5eV or It is lower.
P-doping agent may include at least one in the compound selected from quinone derivative, metal oxide and cyano-containing, but It is embodiment of the present disclosure not limited to this.
For example, p-doping agent may include selected from least one in following：
(such as four cyanogen quinones bismethane (TCNQ) and the fluoro- cyanogen dimethyl of 7,7,8,8- tetra- of 2,3,5,6- tetra- are to benzene for quinone derivative Quinone (F4-TCNQ))；
Metal oxide (such as tungsten oxide or molybdenum oxide)；
The nitrile (HAT-CN) of six azepine benzophenanthrenes of 1,4,5,8,9,11--six；And
The compound represented by following formula 221：
But embodiment of the present disclosure not limited to this：
<Formula 221>
In formula 221,
R221To R223Substituted or unsubstituted C can be each independently selected from3-C10Cycloalkyl, substituted or unsubstituted C1-C10 Heterocyclylalkyl, substituted or unsubstituted C3-C10Cycloalkenyl group, substituted or unsubstituted C1-C10It is heterocycloalkenyl, substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C1-C60Heteroaryl, it is substituted or unsubstituted unit price non-aromatic fused polycycle group and Substituted or unsubstituted the non-aromatic of unit price condenses miscellaneous polycyclic moiety, wherein R221To R223At least one of may include be selected from At least one of lower substitution base：Cyano group ,-F ,-Cl ,-Br ,-I, the C by-F substitutions1-C20Alkyl, the C of quilt-Cl substitutions1-C20 Alkyl, the C of quilt-Br substitutions1-C20Alkyl and the C by-I substitutions1-C20Alkyl.
[luminescent layer in organic layer 150]
When organic light emitting apparatus 10 are full-color organic light emitting device, luminescent layer can be patterned as by red according to sub-pixel Luminescent layer, green light emitting layer or blue light-emitting layer.In one or more implementation methods, luminescent layer can have selected from emitting red light The stacked structure of two or more layers in layer, green light emitting layer and blue light-emitting layer, wherein described two or more layers Contact with each other or separated from one another.In one or more implementation methods, luminescent layer may include selected from red illuminating material, green Two or more materials in luminescent material and blue emitting material, wherein, described two or more kind materials are in a layer In be mixed with each other to launch white light.
Luminescent layer may include main body and dopant.Dopant may include selected from phosphorescent dopants and fluorescent dopants extremely Few one kind.
Based on the main body of 100 weight portions, the amount of the dopant in luminescent layer typically can be in about 0.01 to about 15 weight portion In the range of, but embodiment of the present disclosure not limited to this.
The thickness of luminescent layer can be aboutTo aboutFor example, aboutTo aboutIn the range of.When The thickness of luminescent layer within the range when, lower can obtain the excellent characteristics of luminescence without dramatically increasing in driving voltage.
[main body in luminescent layer]
In one or more implementation methods, main body may include the compound represented by following formula 301.
<Formula 301>
[Ar301]xb11-[(L301)xb1-R301]xb21。
In formula 301,
Ar301Can be substituted or unsubstituted C5-C60Carbocylic radical or substituted or unsubstituted C1-C60Heterocyclic radical,
Xb11 can be 1,2 or 3；
L301Selected from substituted or unsubstituted C3-C10Cycloalkylidene, substituted or unsubstituted C1-C10Sub- Heterocyclylalkyl, substitution Or unsubstituted C3-C10Sub- cycloalkenyl group, substituted or unsubstituted C1-C10Sub- heterocycloalkenyl, substituted or unsubstituted C6-C60Sub- virtue Base, substituted or unsubstituted C1-C60Inferior heteroaryl, the non-aromatic fused polycycle group of substituted or unsubstituted divalence and substitution or The non-aromatic of unsubstituted divalence condenses miscellaneous polycyclic moiety；
Xb1 can be the integer selected from 0 to 5,
R301May be selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, substitution or unsubstituted C1-C60Alkyl, substituted or unsubstituted C2-C60Alkenyl, substituted or unsubstituted C2-C60Alkynyl, substituted or unsubstituted C1- C60Alkoxy, substituted or unsubstituted C3-C10Cycloalkyl, substituted or unsubstituted C1-C10It is Heterocyclylalkyl, substituted or unsubstituted C3-C10Cycloalkenyl group, substituted or unsubstituted C1-C10Heterocycloalkenyl, substituted or unsubstituted C6-C60Aryl, substitution or unsubstituted C6-C60Aryloxy group, substituted or unsubstituted C6-C60Arylthio, substituted or unsubstituted C1-C60Heteroaryl, substitution do not take The univalent non-aromatic fused polycycle group in generation, substituted or unsubstituted the non-aromatic of unit price condense miscellaneous polycyclic moiety ,-Si (Q301)(Q302)(Q303)、-N(Q301)(Q302)、-B(Q301)(Q302) ,-C (=O) (Q301) ,-S (=O)2(Q301) and-P (=O) (Q301)(Q302),
Xb21 can be the integer selected from 1 to 5,
Wherein Q301To Q303C can be each independently selected from1-C10Alkyl, C1-C10Alkoxy, phenyl, xenyl, terphenyl Base and naphthyl, but embodiment of the present disclosure not limited to this.
In one or more implementation methods, in formula 301, Ar301May be selected from：
Naphthyl, fluorenyl, the fluorenyl of spiral shell-two, benzo fluorenyl, dibenzo fluorenyl, non-that alkenyl, phenanthryl, anthryl, fluoranthene base, benzene And phenanthryl, pyrenyl, Qu Ji, aphthacene base, Pi base, perylene base, pentaphene base, indeno anthryl, dibenzofuran group and dibenzothiophenes Base；And
Each it is selected from the substituted naphthyl of following at least one, fluorenyl, the fluorenyl of spiral shell-two, benzo fluorenyl, dibenzo fluorenes Base, non-that alkenyl, phenanthryl, anthryl, fluoranthene base, benzo phenanthryl, pyrenyl, Qu Ji, aphthacene base, Pi base, perylene base, pentaphene base, indenes And anthryl, dibenzofuran group and dibenzothiophenes base：Deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, Hydrazone group, C1-C20Alkyl, C1-C20Alkoxy, phenyl, xenyl, terphenyl, naphthyl ,-Si (Q31)(Q32)(Q33)、-N(Q31) (Q32)、-B(Q31)(Q32) ,-C (=O) (Q31) ,-S (=O)2(Q31) and-P (=O) (Q31)(Q32),
Wherein Q31To Q33C can be each independently selected from1-C10Alkyl, C1-C10Alkoxy, phenyl, xenyl, terphenyl And naphthyl, but embodiment of the present disclosure not limited to this.
In formula 301, when xb11 is more than or equal to 2, two or more Ar301Can be connected by singly-bound.
In one or more implementation methods, the compound represented by formula 301 can be represented by formula 301-1 or 301-2：
<Formula 301-1>
<Formula 301-2>
In formula 301-1 to 301-2,
A301To A304Phenyl, naphthyl, phenanthryl, fluoranthene base, benzo phenanthryl, pyrenyl, Qu Ji, pyridine can be each independently selected from Base, pyrimidine radicals, indenyl, fluorenyl, the fluorenyl of spiral shell-two, benzo fluorenyl, dibenzo fluorenyl, indyl, carbazyl, benzo carbazole base, two Benzo carbazole base, furyl, benzofuranyl, dibenzofuran group, aphthofurans base, benzo aphthofurans base, dinaphtho furan Mutter base, thienyl, benzothienyl, dibenzothiophenes base, aphthothiophenes base, benzo aphthothiophenes base and dinaphtho thienyl,
X301Can be O, S or N- [(L304)xb4-R304],
R311To R314Can be each independently selected from hydrogen, deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, Hydrazone group, C1-C20Alkyl, C1-C20Alkoxy, phenyl, xenyl, terphenyl, naphthyl ,-Si (Q31)(Q32)(Q33)、-N(Q31) (Q32)、-B(Q31)(Q32) ,-C (=O) (Q31) ,-S (=O)2(Q31) and-P (=O) (Q31)(Q32),
Xb22 and xb23 can be each independently 0,1 or 2,
L301、xb1、R301And Q31To Q33Can be same as described above,
L302To L304Can independently of one another with L301Described is identical,
Xb2 to xb4 can independently of one another with identical described by xb1, and
R302To R304Can independently of one another with R301Described is identical.
For example, in formula 301,301-1 and 301-2, L301To L304Can be each independently selected from：
Phenylene, naphthylene, fluorenylidene, the sub- fluorenyl of spiral shell-two, sub- benzo fluorenyl, sub- dibenzo fluorenyl, phenanthrylene, sub- anthracene Base, sub- fluoranthene base, sub- benzo phenanthryl, sub- pyrenyl, sub- base in the wrong, sub- perylene base, sub- pentaphene base, sub- hexacene base, sub- pentacene base, Asia Thienyl, furylidene, sub- carbazyl, sub- indyl, sub- isoindolyl, sub- benzofuranyl, sub- benzothienyl, sub- hexichol And furyl, sub- dibenzothiophenes base, sub- benzo carbazole base, sub- dibenzo-carbazole base, sub- dibenzo Silole base, Asia Pyridine radicals, sub- imidazole radicals, sub- pyrazolyl, sub- thiazolyl, Asia isothiazolyl, Ya oxazolyl, Ya isoxazolyls, Asia thiadiazolyl group, Ya oxadiazolyls, sub- pyrazinyl, sub- pyrimidine radicals, sub- pyridazinyl, sub- triazine radical, sub- quinolyl, sub- isoquinolyl, sub- benzoquinoline Base, sub- phthalazinyl, sub- naphthyridines base, sub- quinoxalinyl, sub- quinazolyl, sub- cinnolines base, sub- phenanthridinyl, sub- acridinyl, Ya Fei are coughed up Quinoline base, sub- phenazinyl, sub- benzimidazolyl, sub- different benzothiazolyl, sub- benzoxazolyl, Asia Yi benzoxazolyl, Asia triazole Base, sub- tetrazole radical, sub- imidazopyridyl, sub- imidazopyrimidine base and sub- azepine carbazyl；And
Each it is selected from phenylene, naphthylene, fluorenylidene, the sub- fluorenyl of spiral shell-two, the sub- benzene of at least one of the following substitution And fluorenyl, sub- dibenzo fluorenyl, phenanthrylene, anthrylene, sub- fluoranthene base, sub- benzo phenanthryl, sub- pyrenyl, sub- base in the wrong, sub- perylene base, Asia Pentaphene base, sub- hexacene base, sub- pentacene base, sub- thienyl, furylidene, sub- carbazyl, sub- indyl, sub- isoindolyl, Sub- benzofuranyl, sub- benzothienyl, sub- dibenzofuran group, sub- dibenzothiophenes base, sub- benzo carbazole base, sub- dibenzo Carbazyl, sub- dibenzo Silole base, sub- pyridine radicals, sub- imidazole radicals, sub- pyrazolyl, sub- thiazolyl, sub- isothiazolyl, Ya oxazolyls, Ya isoxazolyls, Asia thiadiazolyl group, Ya oxadiazolyl, sub- pyrazinyl, sub- pyrimidine radicals, sub- pyridazinyl, sub- triazine Base, sub- quinolyl, sub- isoquinolyl, sub- benzoquinoline base, sub- phthalazinyl, sub- naphthyridines base, sub- quinoxalinyl, sub- quinazolyl, Sub- cinnolines base, sub- phenanthridinyl, sub- acridinyl, sub- phenanthroline, sub- phenazinyl, sub- benzimidazolyl, sub- different benzothiazolyl, Asia Benzoxazolyl, Asia Yi benzoxazolyl, sub- triazolyl, sub- tetrazole radical, sub- imidazopyridyl, sub- imidazopyrimidine base and Asia Azepine carbazyl：Deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C1-C20Alkyl, C1-C20Alcoxyl It is base, phenyl, xenyl, terphenyl, naphthyl, fluorenyl, the fluorenyl of spiral shell-two, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, anthryl, glimmering Anthryl, benzo phenanthryl, pyrenyl, Qu Ji, perylene base, pentaphene base, hexacene base, pentacene base, thienyl, furyl, carbazyl, Yin Diindyl base, isoindolyl, benzofuranyl, benzothienyl, dibenzofuran group, dibenzothiophenes base, benzo carbazole base, hexichol And it is carbazyl, dibenzo Silole base, pyridine radicals, imidazole radicals, pyrazolyl, thiazolyl, isothiazolyl, oxazolyls, different Oxazolyl, thiadiazolyl group, oxadiazolyls, pyrazinyl, pyrimidine radicals, pyridazinyl, triazine radical, quinolyl, isoquinolyl, benzoquinoline Base, phthalazinyl, naphthyridines base, quinoxalinyl, quinazolyl, cinnolines base, phenanthridinyl, acridinyl, phenanthroline, phenazinyl, benzo Imidazole radicals, different benzothiazolyl, benzoxazolyl, Yi benzoxazolyls, triazolyl, tetrazole radical, imidazopyridyl, imidazo Pyrimidine radicals, azepine carbazyl ,-Si (Q31)(Q32)(Q33)、-N(Q31)(Q32)、-B(Q31)(Q32) ,-C (=O) (Q31) ,-S (= O)2(Q31) and-P (=O) (Q31)(Q32),
Wherein Q31To Q33Can be same as described above.
In one or more implementation methods, in formula 301,301-1 and 301-2, R301To R304Can select independently of one another From：
Phenyl, xenyl, terphenyl, naphthyl, fluorenyl, the fluorenyl of spiral shell-two, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, anthracene Base, fluoranthene base, benzo phenanthryl, pyrenyl, Qu Ji, perylene base, pentaphene base, hexacene base, pentacene base, thienyl, furyl, carbazole Base, indyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuran group, dibenzothiophenes base, benzo carbazole Base, dibenzo-carbazole base, dibenzo Silole base, pyridine radicals, imidazole radicals, pyrazolyl, thiazolyl, isothiazolyl, Evil Oxazolyl, isoxazolyls, thiadiazolyl group, oxadiazolyls, pyrazinyl, pyrimidine radicals, pyridazinyl, triazine radical, quinolyl, isoquinolyl, Benzoquinoline base, phthalazinyl, naphthyridines base, quinoxalinyl, quinazolyl, cinnolines base, phenanthridinyl, acridinyl, phenanthroline, azophenlyene Base, benzimidazolyl, different benzothiazolyl, benzoxazolyl, Yi benzoxazolyls, triazolyl, tetrazole radical, imidazopyridine Base, imidazopyrimidine base and azepine carbazyl；And
Each it is selected from the substituted phenyl of following at least one, xenyl, terphenyl, naphthyl, fluorenyl, the fluorenes of spiral shell-two Base, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, anthryl, fluoranthene base, benzo phenanthryl, pyrenyl, Qu Ji, perylene base, pentaphene base, hexacene Base, pentacene base, thienyl, furyl, carbazyl, indyl, isoindolyl, benzofuranyl, benzothienyl, dibenzo Furyl, dibenzothiophenes base, benzo carbazole base, dibenzo-carbazole base, dibenzo Silole base, pyridine radicals, imidazoles Base, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyls, thiadiazolyl group, oxadiazolyls, pyrazinyl, pyrimidine radicals, rattle away Piperazine base, triazine radical, quinolyl, isoquinolyl, benzoquinoline base, phthalazinyl, naphthyridines base, quinoxalinyl, quinazolyl, cinnolines Base, phenanthridinyl, acridinyl, phenanthroline, phenazinyl, benzimidazolyl, different benzothiazolyl, benzoxazolyl, Yi Ben Bing Evil Oxazolyl, triazolyl, tetrazole radical, imidazopyridyl, imidazopyrimidine base and azepine carbazyl：Deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl Base, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C1-C20Alkyl, C1-C20Alkoxy, phenyl, xenyl, terphenyl, naphthyl, Fluorenyl, the fluorenyl of spiral shell-two, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, anthryl, fluoranthene base, benzo phenanthryl, pyrenyl, Qu Ji, perylene base, Pentaphene base, hexacene base, pentacene base, thienyl, furyl, carbazyl, indyl, isoindolyl, benzofuranyl, benzo Thienyl, dibenzofuran group, dibenzothiophenes base, benzo carbazole base, dibenzo-carbazole base, dibenzo Silole Base, pyridine radicals, imidazole radicals, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyls, thiadiazolyl group, oxadiazolyls, pyrrole Piperazine base, pyrimidine radicals, pyridazinyl, triazine radical, quinolyl, isoquinolyl, benzoquinoline base, phthalazinyl, naphthyridines base, quinoxalinyl, Quinazolyl, cinnolines base, phenanthridinyl, acridinyl, phenanthroline, phenazinyl, benzimidazolyl, different benzothiazolyl, Ben Bing Evil Oxazolyl, Yi benzoxazolyls, triazolyl, tetrazole radical, imidazopyridyl, imidazopyrimidine base, azepine carbazyl ,-Si (Q31) (Q32)(Q33)、-N(Q31)(Q32)、-B(Q31)(Q32) ,-C (=O) (Q31) ,-S (=O)2(Q31) and-P (=O) (Q31)(Q32),
Wherein Q31To Q33Can be same as described above.
In one or more implementation methods, main body may include alkaline-earth metal complex.For example, main body may be selected from Be complexings Thing (for example, compound H55), Mg complex compounds and Zn complex compounds.
Main body may include selected from 9,10- bis- (2- naphthyls) anthracene (ADN), double (naphthalene -2- bases) anthracenes (MADN) of 2- methyl -9,10-, 9,10- bis--(2- the naphthyls) -2- tert-butyl groups-anthracene (TBADN), 4,4 '-bis- (N- carbazyls) -1,1 '-biphenyl (CBP), 1,3- bis- - At least one in 9- carbazyls benzene (mCP), 1,3,5- tri- (carbazole -9- bases) benzene (TCP) and compound H1 to H55, but this Disclosed embodiment not limited to this.
[being included in the phosphorescent dopants in the luminescent layer in organic layer 150]
Phosphorescent dopants may include the metal-organic complex represented by following formula 401：
<Formula 401>
M(L401)xc1(L402)xc2
In formula 401,
M may be selected from iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh) and thulium (Tm),
L401The ligand that optional free style 402 is represented, and xc1 can be 1,2 or 3, wherein, when xc1 is more than or equal to 2 When, two or more L401Can be same to each other or different to each other,
L402Can be organic ligand, and xc2 can be the integer selected from 0 to 4, wherein, when xc2 is more than or equal to 2, Two or more L402Can be same to each other or different to each other,
<Formula 402>
In formula 402,
X401To X404Nitrogen or carbon can be each independently,
X401And X403Can be connected by singly-bound or double bond；And X402And X404Can be connected by singly-bound or double bond,
A401And A402C can be each independently5-C60Carbocylic radical or C1-C60Heterocyclic radical,
X405Can be singly-bound, *-O-*', *-S-*', *-C (=O)-* ', *-N (Q411)-*'、*-C(Q411)(Q412)-*'、*- C(Q411)=C (Q412)-*'、*-C(Q411)=* ' or *=C (Q411)=* ', wherein Q411And Q412Can be hydrogen, deuterium, C1-C20Alkane Base, C1-C20Alkoxy, phenyl, xenyl, terphenyl or naphthyl,
X406Can be singly-bound, O or S,
R401And R402Can be each independently selected from hydrogen, deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, Hydrazone group, substituted or unsubstituted C1-C20Alkyl, substituted or unsubstituted C1-C20Alkoxy, substituted or unsubstituted C3-C10Ring Alkyl, substituted or unsubstituted C1-C10Heterocyclylalkyl, substituted or unsubstituted C3-C10Cycloalkenyl group, substituted or unsubstituted C1- C10Heterocycloalkenyl, substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C6-C60It is aryloxy group, substituted or unsubstituted C6-C60Arylthio, substituted or unsubstituted C1-C60Heteroaryl, it is substituted or unsubstituted unit price non-aromatic fused polycycle group, Substituted or unsubstituted the non-aromatic of unit price condenses miscellaneous polycyclic moiety ,-Si (Q401)(Q402)(Q403)、-N(Q401)(Q402)、-B (Q401)(Q402) ,-C (=O) (Q401) ,-S (=O)2(Q401) and-P (=O) (Q401)(Q402), wherein Q401To Q403Can be each only On the spot it is selected from C1-C10Alkyl, C1-C10Alkoxy, C6-C20Aryl and C1-C20Heteroaryl,
Xc11 and xc12 can be each independently the integer selected from 0 to 10, and
* and * ' in formula 402 each represent the binding site with the M in formula 401.
In one or more implementation methods, the A in formula 402401And A402Phenyl, naphthyl, fluorenes can be each independently selected from Base, the fluorenyl of spiral shell-two, indenyl, pyrrole radicals, thienyl, furyl, imidazole radicals, pyrazolyl, thiazolyl, isothiazolyl, oxazolyls, Isoxazolyl, pyridine radicals, pyrazinyl, pyrimidine radicals, pyridazinyl, quinolyl, isoquinolyl, benzoquinoline base, quinoxalinyl, quinoline azoles Quinoline base, carbazyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzo-thienyl, benzoxazolyl, Yi Ben Bing Evil Oxazolyl, triazolyl, tetrazole radical, oxadiazolyls, triazine radical, dibenzofuran group and dibenzothiophenes base.
In one or more implementation methods, in formula 402, i) X401Can be nitrogen, and X402Can be carbon, or ii) X401 And X402Can be simultaneously each nitrogen.
In one or more implementation methods, the R in formula 402401And R402Can be each independently selected from：
Hydrogen, deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C1-C20Alkyl and C1-C20Alkane Epoxide；
Each it is selected from the substituted C of following at least one1-C20Alkyl and C1-C20Alkoxy：Deuterium ,-F ,-Cl ,-Br ,- I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, phenyl, naphthyl, cyclopenta, cyclohexyl, adamantyl, norcamphane base and drop Amphene base；
Cyclopenta, cyclohexyl, adamantyl, norcamphane base, norcamphene base, phenyl, xenyl, terphenyl, naphthyl, fluorenes Base, pyridine radicals, pyrazinyl, pyrimidine radicals, pyridazinyl, triazine radical, quinolyl, isoquinolyl, quinoxalinyl, quinazolyl, carbazole Base, dibenzofuran group and dibenzothiophenes base；
Each it is selected from the substituted cyclopenta of following at least one, cyclohexyl, adamantyl, norcamphane base, norcamphene Base, phenyl, xenyl, terphenyl, naphthyl, fluorenyl, pyridine radicals, pyrazinyl, pyrimidine radicals, pyridazinyl, triazine radical, quinolyl, Isoquinolyl, quinoxalinyl, quinazolyl, carbazyl, dibenzofuran group and dibenzothiophenes base：Deuterium ,-F ,-Cl ,-Br ,- I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C1-C20Alkyl, C1-C20Alkoxy, cyclopenta, cyclohexyl, adamantyl, Norcamphane base, norcamphene base, phenyl, xenyl, terphenyl, naphthyl, fluorenyl, pyridine radicals, pyrazinyl, pyrimidine radicals, pyridazinyl, Triazine radical, quinolyl, isoquinolyl, quinoxalinyl, quinazolyl, carbazyl, dibenzofuran group and dibenzothiophenes base；With And
-Si(Q401)(Q402)(Q403)、-N(Q401)(Q402)、-B(Q401)(Q402) ,-C (=O) (Q401) ,-S (=O)2 (Q401) and-P (=O) (Q401)(Q402),
Wherein Q401To Q403C can be each independently selected from1-C10Alkyl, C1-C10Alkoxy, phenyl, xenyl and naphthyl, But embodiment of the present disclosure not limited to this.
In one or more implementation methods, in formula 401, when xc1 is more than or equal to 2, in two or more L401 In, two A401Optionally pass through linking group X407It is connected to each other, or in two or more L401In, two A402Can appoint Selection of land passes through linking group X408Connection is (referring to compound PD1 to PD4 and PD7).X407And X408List can be each independently Key, *-O-*', *-S-*', *-C (=O)-* ', *-N (Q413)-*'、*-C(Q413)(Q414)-* ' or *-C (Q413)=C (Q414)-* ' (wherein Q413And Q414Hydrogen, deuterium, C can be each independently1-C20Alkyl, C1-C20Alkoxy, phenyl, xenyl, three Xenyl or naphthyl), but embodiment of the present disclosure not limited to this.
L in formula 401402Can be unit price, divalence or trivalent organic ligand.For example, L402May be selected from halogen, diketone (example Such as, acetylacetonate), carboxylic acid (for example, pyridine carboxylic acid salt) ,-C (=O), isonitrile ,-CN and phosphorus is (for example, hydrogen phosphide or phosphorous Hydrochlorate), but embodiment of the present disclosure not limited to this.
In one or more implementation methods, phosphorescent dopants may be selected from, for example, compound PD1 to PD25, but this public affairs The implementation method not limited to this opened：
[fluorescent dopants in luminescent layer].
Fluorescent dopants may include novel arylamine compound or styrylamine compound.
Fluorescent dopants may include the compound represented by following formula 501：
<Formula 501>
In formula 501,
Ar501Can be substituted or unsubstituted C5-C60Carbocylic radical or substituted or unsubstituted C1-C60Heterocyclic radical,
L501To L503Substituted or unsubstituted C can be each independently selected from3-C10Cycloalkylidene, substituted or unsubstituted C1- C10Sub- Heterocyclylalkyl, substituted or unsubstituted C3-C10Sub- cycloalkenyl group, substituted or unsubstituted C1-C10Sub- heterocycloalkenyl, substitution or Unsubstituted C6-C60Arlydene, substituted or unsubstituted C1-C60Inferior heteroaryl, substituted or unsubstituted divalence it is non-aromatic thick Close polycyclic moiety and the non-aromatic of substituted or unsubstituted divalence condense miscellaneous polycyclic moiety,
Xd1 to xd3 can be each independently 0 to 3 integer,
R501And R502Substituted or unsubstituted C can be each independently selected from3-C10Cycloalkyl, substituted or unsubstituted C1-C10 Heterocyclylalkyl, substituted or unsubstituted C3-C10Cycloalkenyl group, substituted or unsubstituted C1-C10It is heterocycloalkenyl, substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C6-C60Aryloxy group, substituted or unsubstituted C6-C60It is arylthio, substituted or unsubstituted C1-C60Heteroaryl, it is substituted or unsubstituted unit price non-aromatic fused polycycle group and it is substituted or unsubstituted unit price it is non-aromatic Race condenses miscellaneous polycyclic moiety, and
Xd4 can be 1 to 6 integer.
In one or more implementation methods, the Ar in formula 501501May be selected from：
Naphthyl, heptalene base, fluorenyl, the fluorenyl of spiral shell-two, benzo fluorenyl, dibenzo fluorenyl, non-that alkenyl, phenanthryl, anthryl, Fluoranthene base, benzo phenanthryl, pyrenyl, Qu Ji, aphthacene base, Pi base, perylene base, pentaphene base, indeno anthryl and indeno phenanthryl；And
Each be selected from the substituted naphthyl of following at least one, heptalene base, fluorenyl, the fluorenyl of spiral shell-two, benzo fluorenyl, Dibenzo fluorenyl, non-that alkenyl, phenanthryl, anthryl, fluoranthene base, benzo phenanthryl, pyrenyl, Qu Ji, aphthacene base, Pi base, perylene base, penta Fen Ji, indeno anthryl and indeno phenanthryl：Deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C1-C20 Alkyl, C1-C20Alkoxy, phenyl, xenyl, terphenyl and naphthyl.
In one or more implementation methods, the L in formula 501501To L503Can be each independently selected from：
Phenylene, naphthylene, fluorenylidene, the sub- fluorenyl of spiral shell-two, sub- benzo fluorenyl, sub- dibenzo fluorenyl, phenanthrylene, sub- anthracene Base, sub- fluoranthene base, sub- benzo phenanthryl, sub- pyrenyl, sub- base in the wrong, sub- perylene base, sub- pentaphene base, sub- hexacene base, sub- pentacene base, Asia Thienyl, furylidene, sub- carbazyl, sub- indyl, sub- isoindolyl, sub- benzofuranyl, sub- benzothienyl, sub- hexichol And furyl, sub- dibenzothiophenes base, sub- benzo carbazole base, sub- dibenzo-carbazole base, sub- dibenzo Silole base and Sub- pyridine radicals；And
Each it is selected from the substituted phenylene of following at least one, naphthylene, fluorenylidene, the sub- fluorenyl of spiral shell-two, sub- benzo Fluorenyl, sub- dibenzo fluorenyl, phenanthrylene, anthrylene, sub- fluoranthene base, sub- benzo phenanthryl, sub- pyrenyl, sub- base in the wrong, sub- perylene base, sub- penta Fen Ji, sub- hexacene base, sub- pentacene base, sub- thienyl, furylidene, sub- carbazyl, sub- indyl, sub- isoindolyl, Asia Benzofuranyl, sub- benzothienyl, sub- dibenzofuran group, sub- dibenzothiophenes base, sub- benzo carbazole base, sub- dibenzo click Oxazolyl, sub- dibenzo Silole base and sub- pyridine radicals：Deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, hydrazine Base, hydrazone group, C1-C20Alkyl, C1-C20Alkoxy, phenyl, xenyl, terphenyl, naphthyl, fluorenyl, the fluorenyl of spiral shell-two, benzfluorene Base, dibenzo fluorenyl, phenanthryl, anthryl, fluoranthene base, benzo phenanthryl, pyrenyl, Qu Ji, perylene base, pentaphene base, hexacene base, pentacene Base, thienyl, furyl, carbazyl, indyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuran group, two Benzothienyl, benzo carbazole base, dibenzo-carbazole base, dibenzo Silole base and pyridine radicals.
In one or more implementation methods, the R in formula 501501And R502Can be each independently selected from：
Phenyl, xenyl, terphenyl, naphthyl, fluorenyl, the fluorenyl of spiral shell-two, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, anthracene Base, fluoranthene base, benzo phenanthryl, pyrenyl, Qu Ji, perylene base, pentaphene base, hexacene base, pentacene base, thienyl, furyl, carbazole Base, indyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuran group, dibenzothiophenes base, benzo carbazole Base, dibenzo-carbazole base, dibenzo Silole base and pyridine radicals；And
Each it is selected from the substituted phenyl of following at least one, xenyl, terphenyl, naphthyl, fluorenyl, the fluorenes of spiral shell-two Base, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, anthryl, fluoranthene base, benzo phenanthryl, pyrenyl, Qu Ji, perylene base, pentaphene base, hexacene Base, pentacene base, thienyl, furyl, carbazyl, indyl, isoindolyl, benzofuranyl, benzothienyl, dibenzo Furyl, dibenzothiophenes base, benzo carbazole base, dibenzo-carbazole base, dibenzo Silole base and pyridine radicals：Deuterium ,- F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C1-C20Alkyl, C1-C20Alkoxy, phenyl, xenyl, Terphenyl, naphthyl, fluorenyl, the fluorenyl of spiral shell-two, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, anthryl, fluoranthene base, benzo phenanthryl, pyrene Base, Qu Ji, perylene base, pentaphene base, hexacene base, pentacene base, thienyl, furyl, carbazyl, indyl, isoindolyl, benzene And furyl, benzothienyl, dibenzofuran group, dibenzothiophenes base, benzo carbazole base, dibenzo-carbazole base, dibenzo Silole base, pyridine radicals and-Si (Q31)(Q32)(Q33),
Wherein Q31To Q33May be selected from C1-C10Alkyl, C1-C10Alkoxy, phenyl, xenyl, terphenyl and naphthyl.
In one or more implementation methods, the xd4 in formula 501 can be 2, but embodiment of the present disclosure is not limited to This.
For example, fluorescent dopants may be selected from compound FD1 to FD22：
In one or more implementation methods, fluorescent dopants may be selected from following compound, but the embodiment party of the disclosure Formula not limited to this：
[the electric transmission area in organic layer 150]
Electric transmission area can have i) includes single layer structure, the ii of single layer (single layer includes single material)) bag Include the single layer structure or iii of single layer (single layer include various different materials)) have and include various different materials The sandwich construction of multiple layers.
Electric transmission area may include electron transfer layer (ETL), and selected from cushion, hole blocking layer, Electronic Control layer With at least one of electron injecting layer layer, but embodiment of the present disclosure not limited to this.
For example, electric transmission area can have electron transfer layer/electron injection Rotating fields, hole blocking layer/electron transfer layer/ Electron injection Rotating fields, Electronic Control layer/electron transfer layer/electron injection Rotating fields or cushion/electron transfer layer/electronics note Enter Rotating fields, wherein for every kind of structure, constituting layer and being stacked gradually from luminescent layer.However, the implementation of the structure in electric transmission area Mode not limited to this.
In one or more implementation methods, electric transmission area may include the compound of the formula 1 according to implementation method.
Electron transfer layer may include the compound of the formula 1 according to implementation method.
Electric transmission area is (for example, cushion, hole blocking layer, Electronic Control floor or electric transmission in electric transmission area Layer) may include without metallic compound, this without metallic compound contain that at least one pi-electron exhausts containing azo-cycle.
" pi-electron exhaust containing azo-cycle " represents the C as loop portion with least one *-N=*' parts1-C60Heterocycle Base.
For example, " pi-electron exhaust containing azo-cycle " can be i) five yuan to seven yuan miscellaneous lists with least one *-N=*' parts Cyclic group, ii) miscellaneous polycyclic moiety, each five yuan to seven yuan with least one *-N=*' parts of two of which or more Heteromonocyclic group group condenses each other, or iii) miscellaneous polycyclic moiety, wherein at least one is each with least one *-N=*' parts Five yuan to seven yuan heteromonocyclic groups group with least one C5-C60Carbocylic radical is condensed.
The example containing azo-cycle that pi-electron exhausts includes imidazoles, pyrazoles, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrrole Piperazine, pyrimidine, pyridazine, indazole, purine, quinoline, isoquinolin, benzoquinoline, phthalazines, naphthyridines, quinoxaline, quinazoline, cinnolines, phenanthrene Pyridine, acridine, phenanthroline, azophenlyene, benzimidazole, different benzothiazole, benzoxazole, Yi benzoxazoles, triazole, tetrazolium, oxadiazoles, Triazine, thiadiazoles, imidazopyridine, imidazopyrimidine and azepine carbazole, but embodiment of the present disclosure not limited to this.
For example, electric transmission area may include the compound represented by formula 601：
<Formula 601>
[Ar601]xe11-[(L601)xe1-R601]xe21。
In formula 601,
Ar601Can be substituted or unsubstituted C5-C60Carbocylic radical or substituted or unsubstituted C1-C60Heterocyclic radical,
Xe11 can be 1,2 or 3,
L601Selected from substituted or unsubstituted C3-C10Cycloalkylidene, substituted or unsubstituted C1-C10Sub- Heterocyclylalkyl, substitution Or unsubstituted C3-C10Sub- cycloalkenyl group, substituted or unsubstituted C1-C10Sub- heterocycloalkenyl, substituted or unsubstituted C6-C60Sub- virtue Base, substituted or unsubstituted C1-C60Inferior heteroaryl, the non-aromatic fused polycycle group of substituted or unsubstituted divalence and substitution or The non-aromatic of unsubstituted divalence condenses miscellaneous polycyclic moiety,
Xe1 can be the integer selected from 0 to 5,
R601May be selected from substituted or unsubstituted C3-C10Cycloalkyl, substituted or unsubstituted C1-C10Heterocyclylalkyl, substitution or Unsubstituted C3-C10Cycloalkenyl group, substituted or unsubstituted C1-C10Heterocycloalkenyl, substituted or unsubstituted C6-C60Aryl, substitution Or unsubstituted C6-C60Aryloxy group, substituted or unsubstituted C6-C60Arylthio, substituted or unsubstituted C1-C60Heteroaryl, take The non-aromatic fused polycycle group of generation or unsubstituted unit price, substituted or unsubstituted the non-aromatic of unit price condense miscellaneous many ring groups Group ,-Si (Q601)(Q602)(Q603) ,-C (=O) (Q601) ,-S (=O)2(Q601) and-P (=O) (Q601)(Q602),
Wherein Q601To Q603C can be each independently1-C10Alkyl, C1-C10Alkoxy, phenyl, xenyl, terphenyl Or naphthyl, and
Xe21 can be the integer selected from 1 to 5.
In one or more implementation methods, selected from the Ar that quantity is xe11601With the R that quantity is xe21601In At least one may include that pi-electron exhausts containing azo-cycle.
In one or more implementation methods, the ring Ar in formula 601601May be selected from：
Phenyl, naphthyl, fluorenyl, the fluorenyl of spiral shell-two, benzo fluorenyl, dibenzo fluorenyl, non-that alkenyl, phenanthryl, anthryl, fluoranthene Base, benzo phenanthryl, pyrenyl, Qu Ji, aphthacene base, Pi base, perylene base, pentaphene base, indeno anthryl, dibenzofuran group, dibenzo It is thienyl, carbazyl, imidazole radicals, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyls, pyridine radicals, pyrazinyl, phonetic Piperidinyl, pyridazinyl, indazolyl, purine radicals, quinolyl, isoquinolyl, benzoquinoline base, phthalazinyl, naphthyridines base, quinoxalinyl, Quinazolyl, cinnolines base, phenanthridinyl, acridinyl, phenanthroline, phenazinyl, benzimidazolyl, different benzothiazolyl, Ben Bing Evil Oxazolyl, Yi benzoxazolyls, triazolyl, tetrazole radical, oxadiazolyls, triazine radical, thiadiazolyl group, imidazopyridyl, imidazo Pyrimidine radicals and azepine carbazyl；And
Each it is selected from the substituted phenyl of following at least one, naphthyl, fluorenyl, the fluorenyl of spiral shell-two, benzo fluorenyl, hexichol And fluorenyl, non-that alkenyl, phenanthryl, anthryl, fluoranthene base, benzo phenanthryl, pyrenyl, Qu Ji, aphthacene base, Pi base, perylene base, pentaphene Base, indeno anthryl, dibenzofuran group, dibenzothiophenes base, carbazyl, imidazole radicals, pyrazolyl, thiazolyl, isothiazolyl, Evil Oxazolyl, isoxazolyls, pyridine radicals, pyrazinyl, pyrimidine radicals, pyridazinyl, indazolyl, purine radicals, quinolyl, isoquinolyl, benzo Quinolyl, phthalazinyl, naphthyridines base, quinoxalinyl, quinazolyl, cinnolines base, phenanthridinyl, acridinyl, phenanthroline, phenazinyl, Benzimidazolyl, different benzothiazolyl, benzoxazolyl, Yi benzoxazolyls, triazolyl, tetrazole radical, oxadiazolyls, triazine Base, thiadiazolyl group, imidazopyridyl, imidazopyrimidine base and azepine carbazyl：Deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, Nitro, amidino groups, diazanyl, hydrazone group, C1-C20Alkyl, C1-C20Alkoxy, phenyl, xenyl, terphenyl, naphthyl ,-Si (Q31) (Q32)(Q33) ,-S (=O)2(Q31) and-P (=O) (Q31)(Q32),
Wherein Q31To Q33C can be each independently selected from1-C10Alkyl, C1-C10Alkoxy, phenyl, xenyl, terphenyl And naphthyl.
When the xe11 in formula 601 is more than or equal to 2, two or more Ar601Can be connected by singly-bound.
In one or more implementation methods, the Ar in formula 601601It can be anthryl.
In one or more implementation methods, the compound represented by formula 601 can be represented by formula 601-1：
<Formula 601-1>
In formula 601-1,
X614Can be N or C (R614), X615Can be N or C (R615), X616Can be N or C (R616), and selected from X614To X616In At least one can be N,
L611To L613Can independently of one another with L601Described is identical,
Xe611 to xe613 can independently of one another with identical described by xe1,
R611To R613Can independently of one another with R601Described is identical,
R614To R616Can be each independently selected from hydrogen, deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, Hydrazone group, C1-C20Alkyl, C1-C20Alkoxy, phenyl, xenyl, terphenyl and naphthyl.
In one or more implementation methods, in formula 601 and 601-1, L601And L611To L613Can select independently of one another From：
Phenylene, naphthylene, fluorenylidene, the sub- fluorenyl of spiral shell-two, sub- benzo fluorenyl, sub- dibenzo fluorenyl, phenanthrylene, sub- anthracene Base, sub- fluoranthene base, sub- benzo phenanthryl, sub- pyrenyl, sub- base in the wrong, sub- perylene base, sub- pentaphene base, sub- hexacene base, sub- pentacene base, Asia Thienyl, furylidene, sub- carbazyl, sub- indyl, sub- isoindolyl, sub- benzofuranyl, sub- benzothienyl, sub- hexichol And furyl, sub- dibenzothiophenes base, sub- benzo carbazole base, sub- dibenzo-carbazole base, sub- dibenzo Silole base, Asia Pyridine radicals, sub- imidazole radicals, sub- pyrazolyl, sub- thiazolyl, Asia isothiazolyl, Ya oxazolyl, Ya isoxazolyls, Asia thiadiazolyl group, Ya oxadiazolyls, sub- pyrazinyl, sub- pyrimidine radicals, sub- pyridazinyl, sub- triazine radical, sub- quinolyl, sub- isoquinolyl, sub- benzoquinoline Base, sub- phthalazinyl, sub- naphthyridines base, sub- quinoxalinyl, sub- quinazolyl, sub- cinnolines base, sub- phenanthridinyl, sub- acridinyl, Ya Fei are coughed up Quinoline base, sub- phenazinyl, sub- benzimidazolyl, sub- different benzothiazolyl, sub- benzoxazolyl, Asia Yi benzoxazolyl, Asia triazole Base, sub- tetrazole radical, sub- imidazopyridyl, sub- imidazopyrimidine base and sub- azepine carbazyl；And
Each it is selected from the substituted phenylene of following at least one, naphthylene, fluorenylidene, the sub- fluorenyl of spiral shell-two, sub- benzo Fluorenyl, sub- dibenzo fluorenyl, phenanthrylene, anthrylene, sub- fluoranthene base, sub- benzo phenanthryl, sub- pyrenyl, sub- base in the wrong, sub- perylene base, sub- penta Fen Ji, sub- hexacene base, sub- pentacene base, sub- thienyl, furylidene, sub- carbazyl, sub- indyl, sub- isoindolyl, Asia Benzofuranyl, sub- benzothienyl, sub- dibenzofuran group, sub- dibenzothiophenes base, sub- benzo carbazole base, sub- dibenzo click Oxazolyl, sub- dibenzo Silole base, sub- pyridine radicals, sub- imidazole radicals, sub- pyrazolyl, sub- thiazolyl, sub- isothiazolyl, Asia Oxazolyl, Ya isoxazolyls, Asia thiadiazolyl group, Ya oxadiazolyl, sub- pyrazinyl, sub- pyrimidine radicals, sub- pyridazinyl, sub- triazine radical, Sub- quinolyl, sub- isoquinolyl, sub- benzoquinoline base, sub- phthalazinyl, sub- naphthyridines base, sub- quinoxalinyl, sub- quinazolyl, Asia are scolded Quinoline base, sub- phenanthridinyl, sub- acridinyl, sub- phenanthroline, sub- phenazinyl, sub- benzimidazolyl, sub- different benzothiazolyl, sub- benzo Oxazolyl, Asia Yi benzoxazolyl, sub- triazolyl, sub- tetrazole radical, sub- imidazopyridyl, sub- imidazopyrimidine base and sub- azepine Carbazyl：Deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C1-C20Alkyl, C1-C20Alkoxy, Phenyl, xenyl, terphenyl, naphthyl, fluorenyl, the fluorenyl of spiral shell-two, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, anthryl, fluoranthene Base, benzo phenanthryl, pyrenyl, Qu Ji, perylene base, pentaphene base, hexacene base, pentacene base, thienyl, furyl, carbazyl, indoles Base, isoindolyl, benzofuranyl, benzothienyl, dibenzofuran group, dibenzothiophenes base, benzo carbazole base, dibenzo Carbazyl, dibenzo Silole base, pyridine radicals, imidazole radicals, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, Yi Evil Oxazolyl, thiadiazolyl group, oxadiazolyls, pyrazinyl, pyrimidine radicals, pyridazinyl, triazine radical, quinolyl, isoquinolyl, benzoquinoline Base, phthalazinyl, naphthyridines base, quinoxalinyl, quinazolyl, cinnolines base, phenanthridinyl, acridinyl, phenanthroline, phenazinyl, benzo Imidazole radicals, different benzothiazolyl, benzoxazolyl, Yi benzoxazolyls, triazolyl, tetrazole radical, imidazopyridyl, imidazo Pyrimidine radicals and azepine carbazyl, but embodiment of the present disclosure not limited to this.
In one or more implementation methods, in formula 601 and 601-1, xe1 and xe611 to xe613 can be independently of one another It is 0,1 or 2.
In one or more implementation methods, in formula 601 and 601-1, R601And R611To R613Can select independently of one another From：
Phenyl, xenyl, terphenyl, naphthyl, fluorenyl, the fluorenyl of spiral shell-two, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, anthracene Base, fluoranthene base, benzo phenanthryl, pyrenyl, Qu Ji, perylene base, pentaphene base, hexacene base, pentacene base, thienyl, furyl, carbazole Base, indyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuran group, dibenzothiophenes base, benzo carbazole Base, dibenzo-carbazole base, dibenzo Silole base, pyridine radicals, imidazole radicals, pyrazolyl, thiazolyl, isothiazolyl, Evil Oxazolyl, isoxazolyls, thiadiazolyl group, oxadiazolyls, pyrazinyl, pyrimidine radicals, pyridazinyl, triazine radical, quinolyl, isoquinolyl, Benzoquinoline base, phthalazinyl, naphthyridines base, quinoxalinyl, quinazolyl, cinnolines base, phenanthridinyl, acridinyl, phenanthroline, azophenlyene Base, benzimidazolyl, different benzothiazolyl, benzoxazolyl, Yi benzoxazolyls, triazolyl, tetrazole radical, imidazopyridine Base, imidazopyrimidine base and azepine carbazyl；
Each it is selected from the substituted phenyl of following at least one, xenyl, terphenyl, naphthyl, fluorenyl, the fluorenes of spiral shell-two Base, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, anthryl, fluoranthene base, benzo phenanthryl, pyrenyl, Qu Ji, perylene base, pentaphene base, hexacene Base, pentacene base, thienyl, furyl, carbazyl, indyl, isoindolyl, benzofuranyl, benzothienyl, dibenzo Furyl, dibenzothiophenes base, benzo carbazole base, dibenzo-carbazole base, dibenzo Silole base, pyridine radicals, imidazoles Base, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyls, thiadiazolyl group, oxadiazolyls, pyrazinyl, pyrimidine radicals, rattle away Piperazine base, triazine radical, quinolyl, isoquinolyl, benzoquinoline base, phthalazinyl, naphthyridines base, quinoxalinyl, quinazolyl, cinnolines Base, phenanthridinyl, acridinyl, phenanthroline, phenazinyl, benzimidazolyl, different benzothiazolyl, benzoxazolyl, Yi Ben Bing Evil Oxazolyl, triazolyl, tetrazole radical, imidazopyridyl, imidazopyrimidine base and azepine carbazyl：Deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl Base, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C1-C20Alkyl, C1-C20Alkoxy, phenyl, xenyl, terphenyl, naphthyl, Fluorenyl, the fluorenyl of spiral shell-two, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, anthryl, fluoranthene base, benzo phenanthryl, pyrenyl, Qu Ji, perylene base, Pentaphene base, hexacene base, pentacene base, thienyl, furyl, carbazyl, indyl, isoindolyl, benzofuranyl, benzo Thienyl, dibenzofuran group, dibenzothiophenes base, benzo carbazole base, dibenzo-carbazole base, dibenzo Silole Base, pyridine radicals, imidazole radicals, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyls, thiadiazolyl group, oxadiazolyls, pyrrole Piperazine base, pyrimidine radicals, pyridazinyl, triazine radical, quinolyl, isoquinolyl, benzoquinoline base, phthalazinyl, naphthyridines base, quinoxalinyl, Quinazolyl, cinnolines base, phenanthridinyl, acridinyl, phenanthroline, phenazinyl, benzimidazolyl, different benzothiazolyl, Ben Bing Evil Oxazolyl, Yi benzoxazolyls, triazolyl, tetrazole radical, imidazopyridyl, imidazopyrimidine base and azepine carbazyl；And
- S (=O)2(Q601) and-P (=O) (Q601)(Q602),
Wherein Q601And Q602Can be identical with as described above.
Electric transmission area may include selected from least one of compound ET1 to ET36 compound, but the reality of the disclosure Apply mode not limited to this：
In one or more implementation methods, electric transmission area may include selected from least one of the following compound：2, 9- dimethyl -4,7- diphenyl -1,10- phenanthroline (BCP), 4,7- diphenyl -1,10- phenanthroline (BPhen), Alq3、BAlq、 3- (biphenyl -4- bases) -5- (4- tert-butyl-phenyls) -4- phenyl -4H-1,2,4- triazoles (TAZ) and NTAZ.
The thickness of cushion, hole blocking layer or Electronic Control layer can be aboutTo aboutFor example, about To aboutIn the range of.When the thickness of cushion, hole blocking layer and Electronic Control layer is in the range of these, electronics resistance Barrier lower can have excellent electronic blocking characteristic or Electronic Control characteristic without dramatically increasing in driving voltage.
The thickness of electron transfer layer can be aboutTo aboutFor example, aboutTo aboutScope It is interior.When electron transfer layer thickness within the above range when, electron transfer layer driving voltage without under dramatically increasing can have order The electron transport property of people's satisfaction.
Except materials described above, electric transmission area (for example, the electron transfer layer in electric transmission area) can be further Including the material containing metal.
Material containing metal may include selected from least one in alkali metal complex and alkaline-earth metal complex.Alkali metal Complex compound may include selected from following metal ion：Li ions, Na ions, K ions, Rb ions and Cs ions, and alkaline earth gold Category complex compound may include selected from the metal ion in following：Be ions, Mg ions, Ca ions, Sr ions and Ba ions.With alkali gold The ligand of the metallic ion coordination of category complex compound or alkaline-earth metal complex may be selected from oxyquinoline, isoquinolinol, hydroxyl Benzoquinoline, hydroxy-acridine, hydroxyl phenanthridines, Qiang Ben Ji oxazoles, hydroxyphenyl thiazole, Qiang base Er Ben oxadiazoles, hydroxy diphenyl Thiadiazoles, oxybenzene yl pyridines, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridyl, phenanthroline and cyclopentadiene, but Embodiment of the present disclosure not limited to this.
For example, the material containing metal may include Li complex compounds.For example, Li complex compounds may include compound ET-D1 (8- hydroxyls Quinoline lithium, LiQ) or ET-D2：
Electric transmission area may include to promote the injected electrons implanted layer of the electronics from second electrode 190.The electronics Implanted layer can directly contact second electrode 190.
Electron injecting layer can have i) includes the single layer structure of single layer (single layer includes single material), ii) bag Include the single layer structure or iii of single layer (single layer include various different materials)) have and include various different materials The sandwich construction of multiple layers.
Electron injecting layer may include alkali metal, alkaline-earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, Rare earth compound, alkali metal complex, alkaline-earth metal complex, rare earth metal complex or its any combination.
Alkali metal may be selected from Li, Na, K, Rb and Cs.In one or more implementation methods, alkali metal can for Li, Na or Cs.In one or more implementation methods, alkali metal can be Li or Cs, but embodiment of the present disclosure not limited to this.
Alkaline-earth metal may be selected from Mg, Ca, Sr and Ba.
Rare earth metal may be selected from Sc, Y, Ce, Yb, Gd and Tb.
Alkali metal compound, alkaline earth metal compound and rare earth compound may be selected from alkali metal, alkaline-earth metal and dilute The oxide and halide (for example, fluoride, chloride, bromide or iodide) of earth metal.
Alkali metal compound may be selected from alkali metal oxide (such as Li2O、Cs2O or K2O) and alkali halide (such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI or RbI).In one or more implementation methods, alkali metal compound may be selected from LiF、Li2O, NaF, LiI, NaI, CsI and KI, but embodiment of the present disclosure not limited to this.
Alkaline earth metal compound may be selected from alkaline earth metal compound (such as BaO, SrO, CaO, BaxSr1-xO(0<x<1)、 BaxCa1-xO(0<x<1)).In one or more implementation methods, alkaline earth metal compound may be selected from BaO, SrO and CaO, but Embodiment of the present disclosure not limited to this.
Rare earth compound may be selected from YbF3、ScF3、ScO3、Y2O3、Ce2O3、GdF3And TbF3.In one or more realities Apply in mode, rare earth compound may be selected from YbF3、ScF3、TbF3、YbI3、ScI3And TbI3But, the embodiment party of the disclosure Formula not limited to this.
Alkali metal complex, alkaline-earth metal complex and rare earth metal complex may include alkali metal as described above Ion, alkaline-earth metal ions and rare earth ion, and with alkali metal complex, alkaline-earth metal complex and rare earth metal network The ligand of the metallic ion coordination of compound can be each independently selected from oxyquinoline, isoquinolinol, hydroxy benzo quinoline, hydroxyl Base acridine, hydroxyl phenanthridines, Qiang Ben Ji oxazoles, hydroxyphenyl thiazole, Qiang base Er Ben oxadiazoles, hydroxy diphenyl thiadiazoles, oxybenzene Yl pyridines, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridyl, phenanthroline and cyclopentadiene, but the implementation of the disclosure Mode not limited to this.
Electron injecting layer can be consisted of：Alkali metal, alkaline-earth metal, rare earth metal, alkali metal as described above Compound, alkaline earth metal compound, rare earth compound, alkali metal complex, alkaline-earth metal complex, rare earth metal complex Or its any combination.In one or more implementation methods, electron injecting layer can further include organic material.Work as electron injection Layer is when further including organic material, alkali metal, alkaline-earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, Rare earth compound, alkali metal complex, alkaline-earth metal complex, rare earth metal complex or its any combination can be equably Or be non-uniformly dispersed in the matrix including organic material.
The thickness of electron injecting layer can be aboutTo aboutFor example, aboutTo aboutIn the range of.Work as electronics The thickness of implanted layer within the above range when, electron injecting layer is in driving voltage without can have gratifying electricity under dramatically increasing Sub- injection properties.
[second electrode 190]
Second electrode 190 may be provided on the organic layer 150 having a structure in which.Second electrode 190 can be negative electrode (its It is electron injection electrode), and in this respect, the material for forming second electrode 190 may be selected from relatively low work content Metal, alloy, conductive compound and its mixture.
Second electrode 190 may include selected from least one of the following：Lithium (Li), silver (Ag), magnesium (Mg), aluminium (Al), aluminium- Lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ITO and IZO, but embodiment of the present disclosure is not limited In this.Second electrode 190 can be transmission electrode, half transmitting electrode or reflecting electrode.
Second electrode 190 can have single layer structure or the sandwich construction including two or more layers.
[description of Fig. 2 to Fig. 4]
The organic light emitting apparatus 20 of Fig. 2 include first the 210, first electricity of coating stacked gradually with the order being specified below Pole 110, organic layer 150 and second electrode 190.The organic light emitting apparatus 30 of Fig. 3 include being stacked gradually with the order being specified below First electrode 110, organic layer 150, the coating 220 of second electrode 190 and second.The organic light emitting apparatus 40 of Fig. 4 include with The first coating 210, first electrode 110, organic layer 150, second electrode 190 and second that the order being specified below is stacked gradually Coating 220.
On Fig. 2 to 4, first electrode 110, organic layer 150 and second electrode 190 refer to the description provided on Fig. 1 To understand.
In the respective organic layer 150 of organic light emitting apparatus 20 and 40, the light produced in luminescent layer may pass through the first electricity Pole 110 (it is half transmitting electrode or transmission electrode) and the first coating 210 tend to outside, and in the He of organic light emitting apparatus 30 In 40 respective organic layers 150, the light of the transmitting produced in luminescent layer may pass through second electrode 190 (it can be semi-transparent radio Pole or transmission electrode) and the trend of the second coating 220 outside.
According to the principle of constructive interference, the first coating 210 and the second coating 220 can increase external light emission efficiency.
First coating 210 and the second coating 220 can be each independently the organic coating layer including organic material, bag Include the inorganic cover layer or the composite coating including organic material and inorganic material of inorganic material.
Can include independently of one another selected from following selected from least one of the first coating 210 and the second coating 220 At least one material：Carbocyclic compound, heterocyclic compound, aminated compounds, derivatives of porphyrin, phthalocyanine derivates, naphthalene phthalocyanine Derivative, alkali metal complex and alkaline-earth metal complex.The carbocyclic compound, heterocyclic compound and aminated compounds can appoint Selection of land is contained the substitution base substitution selected from following at least one element：O, N, S, Se, Si, F, Cl, Br and I.At one or In multiple implementation methods, amine can be independently of one another included selected from least one of the first coating 210 and the second coating 220 Class compound.
In one or more implementation methods, can selected from least one of the first coating 210 and the second coating 220 Include the compound represented by formula 201 or the compound represented by formula 202 independently of one another.
In one or more implementation methods, can selected from least one of the first coating 210 and the second coating 220 Independently of one another including the compound selected from compound HT28 to HT33 and compound CP1 to CP5, but the embodiment party of the disclosure Formula not limited to this.
Hereinbefore, combined Fig. 1-4 describes the organic light emitting apparatus according to implementation method.However, the disclosure Implementation method not limited to this.
The floor for constituting the floor, luminescent layer and composition electric transmission area in hole transport area can be appropriate by using one or more Method formed in a specific area, it is special that methods described is selected from vacuum moulding machine, rotary coating, cast, Langmuir-Brocchi (LB) thermal imaging of deposition, inkjet printing, laser printing and induced with laser.
When the floor of floor, luminescent layer and composition electric transmission area when composition hole transport area is formed by vacuum moulding machine, example Such as, it is contemplated that the structure of the compound that be included in the layer to be formed and the layer to be formed, vacuum moulding machine can be at about 100 DEG C Depositing temperature, about 10 to about 500 DEG C-8Hold in the palm to about 10-3The vacuum peace treaty of supportTo about Deposition speed Carried out under rate.
When the floor of floor, luminescent layer and composition electric transmission area when composition hole transport area is formed by rotary coating, examine Consider the structure of the compound that be included in the layer to be formed and the layer to be formed, rotary coating can be in about 2000rpm extremely Carried out under the coating speed of about 5000rpm and about 80 DEG C to 200 DEG C of heat treatment temperature.
[the general definition of substitution base]
The definition that the substitution base of compound used herein will be hereafter presented (unless defined otherwise, takes for restriction The carbon number of Dai Ji is not restricted, and do not limit the property of substitution base, and the definition and its general definition for replacing base are one Cause).
Term " C as used in this article1-C60Alkyl " refers to 1 to 60 straight or branched saturated fat of carbon atom Race's hydrocarbon monoradical, and the example include methyl, ethyl, propyl group, isobutyl group, sec-butyl, the tert-butyl group, amyl group, isopentyl and Hexyl.Term " C as used in this article1-C60Alkylidene " refers to and C1-C60Alkyl has the divalent group of identical structure.
Term " C as used in this article2-C60Alkenyl " refers in C2-C60The centre or end of alkyl have at least one carbon The alkyl of carbon double bond, and the example includes vinyl, acrylic and cyclobutenyl.Term " C as used in this article2-C60Sub- alkene Base " refers to and C2-C60Alkenyl has the divalent group of identical structure.
Term " C as used in this article2-C60Alkynyl " refers in C2-C60The centre or end of alkyl have at least one carbon The alkyl of the key of carbon three, and example includes acetenyl and propinyl.Term " C as used in this article2-C60Alkynylene " refer to C2-C60Alkynyl has the divalent group of identical structure.
Term " C as used in this article1-C60Alkoxy " refers to by-OA101(wherein A101It is C1-C60Alkyl) represent list Valency group, and the example includes methoxyl group, ethyoxyl and isopropoxy.
Term " C as used in this article3-C10Cycloalkyl " refers to the monocyclic base of monovalent saturated hydrocarbon with 3 to 10 carbon atoms Group, and the example includes cyclopropyl, cyclobutyl, cyclopenta, cyclohexyl and suberyl.Term " C as used in this article3-C10 Cycloalkylidene " refers to and C3-C10Cycloalkyl has the divalent group of identical structure.
Term " C as used in this article1-C10Heterocyclylalkyl " refers to the miscellaneous original selected from N, O, Si, P and S with least one Son is used as ring member nitrogen atoms and the monovalent monocyclic group of 1 to 10 carbon atom, and the example includes 1,2,3,4- oxatriazole pyridines Base, tetrahydrofuran base and tetrahydro-thienyl.Term " C as used in this article1-C10Sub- Heterocyclylalkyl " refers to and C1-C10Heterocycle alkane Base has the divalent group of identical structure.
Term " C as used in this article3-C10Cycloalkenyl group " refers to has 3 to 10 carbon atoms and at least one in its ring Carbon-carbon double bond and the monovalent monocyclic group without armaticity, and the example includes cyclopentenyl, cyclohexenyl group and cycloheptyl Alkenyl.Term " C as used in this article3-C10Sub- cycloalkenyl group " refers to and C3-C10Cycloalkenyl group has the bilvalent radical of identical structure Group.
Term " C as used in this article1-C10Heterocycloalkenyl " refer to have at least one selected from N, O, Si, P in its ring and The hetero atom of S as ring member nitrogen atoms, 1 to 10 carbon atom and at least one double bond monovalent monocyclic group.C1-C10Heterocycloalkenyl Example be 4,5- dihydro -1,2,3,4- oxa-s triazolidinyl, 2,3 dihydro furan base and 2,3- dihydro-thiophene bases.As herein Term " the C for using1-C10Sub- heterocycloalkenyl " refers to and C1-C10Heterocycloalkenyl has the divalent group of identical structure.
Term " C as used in this article6-C60Aryl " refers to including with 6 to 60 carbocyclic aromatic systems of carbon atom Monoradical, and C used herein6-C60Arlydene refers to including with 6 to 60 the two of the carbocyclic aromatic system of carbon atom Valency group.C6-C60The example of aryl is phenyl, naphthyl, anthryl, phenanthryl, pyrenyl and bases.Work as C6-C60Aryl and C6-C60Sub- virtue When base each includes two or more rings, these rings thick each other can connect.
Term " C as used in this article1-C60Heteroaryl " refer to heterocyclic aromatic system (except 1 to 60 carbon atom with Outward, with least one selected from N, O, Si, P and S hetero atom as ring member nitrogen atoms) monoradical.As used in this article Term " C1-C60Inferior heteroaryl " refers to and (in addition to 1 to 60 carbon atom, is selected from at least one with heterocyclic aromatic system The hetero atom of N, O, Si, P and S is used as ring member nitrogen atoms) divalent group.C1-C60The example of heteroaryl be pyridine radicals, pyrimidine radicals, Pyrazinyl, pyridazinyl, triazine radical, quinolyl and isoquinolyl.Work as C1-C60Heteroaryl and C1-C60Inferior heteroaryl each includes two During individual or more ring, these rings thick each other can connect.
Term " C as used in this article6-C60Aryloxy group " refers to by-OA102(wherein A102It is C6-C60Aryl) represent base Group, and C6-C60Arylthio refers to by-SA103(wherein A103It is C6-C60Aryl) represent group.
Term " the non-aromatic fused polycycle group of unit price " as used in this article refers to such monoradical (for example, tool Have 8 to 60 carbon atoms), it has two or more rings for condensing each other, only with carbon atom as ring member nitrogen atoms, and Whole molecular structure does not have armaticity.The instantiation of the non-aromatic fused polycycle group of unit price is fluorenyl.It is used herein Term " the non-aromatic fused polycycle group of divalence " refer to unit price non-aromatic fused polycycle group there is identical structure Divalent group.
Term " the non-aromatic of unit price condenses miscellaneous polycyclic moiety " as used in this article refer to such monoradical (for example, With 1 to 60 carbon atom), it has two or more rings for condensing each other, in addition to carbon atom, also with selected from N, At least one of O, Si, P and S hetero atom are used as ring member nitrogen atoms, and whole molecular structure does not have armaticity.Univalent is non- The example that aromatics condenses miscellaneous polycyclic moiety is carbazyl.Term " the non-aromatic of divalence condenses miscellaneous polycyclic moiety " used herein Refer to and condense miscellaneous polycyclic moiety there is the divalent group of identical structure with the non-aromatic of unit price.
Term " C as used in this article5-C60Carbocylic radical " refer to wherein ring member nitrogen atoms only carbon atom with 5 to 60 The monocyclic or polycyclic moiety of carbon atom.C5-C60Carbocylic radical can be aromatic carbocyclyl groups or non-aromatic carbocyclyl.C5-C60Carbocylic radical can It is ring (such as benzene), monoradical (such as phenyl) or divalent group (such as phenylene).In one or more implementation methods, Depending on being connected to C5-C60The quantity of the substitution base of carbocylic radical, C5-C60Carbocylic radical can be trivalent radical or quaternary groups.
Term " C as used in this article1-C60Heterocyclic radical " refers to and C5-C60Carbocylic radical has mutually isostructural group, simply In addition to carbon (quantity of carbon atom can 1 to 60 in the range of), using selected from least one of N, O, Si, P and S hetero atom As ring member nitrogen atoms.
Substituted C5-C60Carbocylic radical, the C of substitution1-C60Heterocyclic radical, the C of substitution3-C10Cycloalkylidene, the C of substitution1-C10It is sub- Heterocyclylalkyl, the C of substitution3-C10Sub- cycloalkenyl group, the C of substitution1-C10Sub- heterocycloalkenyl, the C of substitution6-C60Arlydene, substitution C1-C60Inferior heteroaryl, the non-aromatic fused polycycle group of divalence of substitution, the divalence of substitution non-aromatic condense miscellaneous polycyclic moiety, take The C in generation1-C60Alkyl, the C of substitution2-C60Alkenyl, the C of substitution2-C60Alkynyl, the C of substitution1-C60Alkoxy, the C of substitution3-C10Ring Alkyl, the C of substitution1-C10Heterocyclylalkyl, the C of substitution3-C10Cycloalkenyl group, the C of substitution1-C10Heterocycloalkenyl, the C of substitution6-C60Virtue Base, the C of substitution6-C60Aryloxy group, the C of substitution6-C60Arylthio, the C of substitution1-C60Heteroaryl, substitution it is univalent non-aromatic thick Univalent non-aromatic at least one of substitution base of the miscellaneous polycyclic moiety substitution base that condenses for closing polycyclic moiety and substitution may be selected from：
Deuterium (- D) ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C1-C60Alkyl, C2-C60Alkene Base, C2-C60Alkynyl and C1-C60Alkoxy；
Each it is selected from the substituted C of following at least one1-C60Alkyl, C2-C60Alkenyl, C2-C60Alkynyl and C1-C60Alkane Epoxide：Deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C3-C10Cycloalkyl, C1-C10Heterocycle alkane Base, C3-C10Cycloalkenyl group, C1-C10Heterocycloalkenyl, C6-C60Aryl, C6-C60Aryloxy group, C6-C60Arylthio, C1-C60Heteroaryl, list The non-aromatic fused polycycle group of valency, the non-aromatic of unit price condense miscellaneous polycyclic moiety ,-Si (Q11)(Q12)(Q13)、-N(Q11) (Q12)、-B(Q11)(Q12) ,-C (=O) (Q11) ,-S (=O)2(Q11) and-P (=O) (Q11)(Q12)；
C3-C10Cycloalkyl, C1-C10Heterocyclylalkyl, C3-C10Cycloalkenyl group, C1-C10Heterocycloalkenyl, C6-C60Aryl, C6-C60Virtue Epoxide, C6-C60Arylthio, C1-C60Heteroaryl, unit price non-aromatic fused polycycle group and unit price it is non-aromatic condense it is miscellaneous polycyclic Group；
Each it is selected from the substituted C of following at least one3-C10Cycloalkyl, C1-C10Heterocyclylalkyl, C3-C10Cycloalkenyl group, C1-C10Heterocycloalkenyl, C6-C60Aryl, C6-C60Aryloxy group, C6-C60Arylthio, C1-C60Heteroaryl, the non-aromatic of unit price are condensed Polycyclic moiety and the non-aromatic of unit price condense miscellaneous polycyclic moiety：Deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, hydrazine Base, hydrazone group, C1-C60Alkyl, C2-C60Alkenyl, C2-C60Alkynyl, C1-C60Alkoxy, C3-C10Cycloalkyl, C1-C10Heterocyclylalkyl, C3-C10Cycloalkenyl group, C1-C10Heterocycloalkenyl, C6-C60Aryl, C6-C60Aryloxy group, C6-C60Arylthio, C1-C60Heteroaryl, unit price Non-aromatic fused polycycle group, unit price non-aromatic condense miscellaneous polycyclic moiety ,-Si (Q21)(Q22)(Q23)、-N(Q21) (Q22)、-B(Q21)(Q22) ,-C (=O) (Q21) ,-S (=O)2(Q21) and-P (=O) (Q21)(Q22)；And
-Si(Q31)(Q32)(Q33)、-N(Q31)(Q32)、-B(Q31)(Q32) ,-C (=O) (Q31) ,-S (=O)2(Q31) and-P (=O) (Q31)(Q32),
Wherein Q11To Q13、Q21To Q23And Q31To Q33Can be each independently selected from hydrogen, deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, Cyano group, nitro, amidino groups, diazanyl, hydrazone group, C1-C60Alkyl, C2-C60Alkenyl, C2-C60Alkynyl, C1-C60Alkoxy, C3-C10Cycloalkanes Base, C1-C10Heterocyclylalkyl, C3-C10Cycloalkenyl group, C1-C10Heterocycloalkenyl, C6-C60Aryl, C1-C60Heteroaryl, unit price it is non-aromatic Fused polycycle group, the non-aromatic of unit price condense miscellaneous polycyclic moiety, xenyl and terphenyl.
Term " Ph " as used in this article represents phenyl；Term " Me " as used in this article represents methyl；As herein The middle term " Et " for using represents ethyl；Term " ter-Bu " as used in this article or " But" represent the tert-butyl group；And such as this Term " OMe " used herein represents methoxyl group.
Term " xenyl " as used in this article refers to " phenyl being substituted by phenyl "." xenyl " is with " C6-C60Virtue Base " is used as " the substituted phenyl " for replacing base.
Term " terphenyl " as used in this article refers to " phenyl replaced by xenyl ".In other words, " terphenyl " It is with by C6-C60The C of aryl substitution6-C60Aryl is used as the substituted phenyl for replacing base.
Unless otherwise defined, * used herein and * ', each refers to the bound site with adjacent atom in corresponding formula Point.
Hereinafter, will be described in detail according to the compound of implementation method and according to implementation with reference to synthesis example and embodiment The organic light emitting apparatus of mode.The term " using B to replace A " used in synthesis example is described refers to the B for using identical molar equivalent Instead of the A of molar equivalent.
Synthesis example
[synthesis example 1：Synthesis compound 2]
Synthetic intermediate I-1
By 5- bromo -1 of 2.59g (10mmol), 10- phenanthroline is dissolved in the tetrahydrofuran (THF) of 40mL, and at -78 DEG C At a temperature of be added to the n-BuLi of 4mL (2.5M is in hexane).After one hour, it is added at the same temperature 2- isopropoxy -4,4,5,5- tetramethyl -1,3,2- Er Evil the borines of 2.0mL (10mmol).Gained mixing is stirred at room temperature Thing 10 hours.Then, water is added to, gained mixture is rinsed three times by using the diethyl ether of 30mL.The diethyl for being rinsed Ether layer is by using MgSO4It is dried, and is dried under reduced pressure.By silica gel column chromatogram separating purification product therefrom Thing, to obtain 1.84g (60% yield) intermediate compound I -1.The compound for being obtained is identified through LC-MS.C18H19BN2O2:M+1 307.2.
Synthetic intermediate I-2
By the intermediate compound I -1 of 3.06g (10.0mmol), the 1- bromo -2- nitrobenzene of 2.02g (10.0mmol), 0.58g Pd (the PPh of (0.50mmol)3)4, 0.16g (0.5mmol) TBAB (TBAB) and 3.18g (30.0mmol) Na2CO3It is dissolved in the toluene/ethanol/H of 60mL2In O (3/3/1) mixed solution, then stirred 16 hours at a temperature of 80 DEG C. Reaction solution is cooled to room temperature.Then, three extraction process are carried out to it by using the water of 60mL and the diethyl ether of 60mL. By using the organic layer that magnesium sulfate drying is obtained by it.Silica gel column chromatography is passed through by the residue obtained from its evaporation solvent Isolated and purified, to obtain the intermediate compound I -2 of 2.20g (73% yield).The compound for being obtained is identified through LC-MS. C18H11N3O2:M+1 302.1
Synthetic intermediate I-3
By the intermediate compound I -2 of 3.01g (10.0mmol), the tin of 3.56g (30mmol) and 5mL (50mmol, concentration 36.5%) hydrochloric acid is dissolved in the ethanol of 60mL, is then stirred 8 hours at a temperature of 100 DEG C.Reaction solution is cooled to room Temperature.Then, filter liquor is obtained by filtering reacting solution under reduced pressure, the NaOH of 3g is dissolved in the water of 10mL, and add Add to filter liquor.Then, three extraction process are carried out to it by using the water of 60mL and the dichloromethane of 60mL.By using The organic layer that magnesium sulfate drying is obtained by it.Separated by silica gel column chromatography by the residue obtained from its evaporation solvent Purifying, to obtain the intermediate compound I -3 of 2.50g (92% yield).The compound for being obtained is identified through LC-MS.C13H13N3:M+1 272.1.
Synthetic intermediate I-4
The intermediate compound I -3 of 2.71g (10mmol) is dissolved in the THF of 30mL, and is slowly added at a temperature of 0 DEG C The etamon (TEA) of 4mL and the 4- bromo-benzoyl chlorides of 3.29g (15mmol).Gained mixture is stirred at room temperature 10 hours.Instead After the completion of answering, three extraction process are carried out to it by using the water of 40mL and the ethyl acetate of 40mL.By using magnesium sulfate The organic layer that drying is obtained by it.Isolated and purified by silica gel column chromatography by the residue obtained from its evaporation solvent, To obtain the intermediate compound I -4 of 3.41g (75% yield).The compound for being obtained is identified through LC-MS.C25H16BrN3O:M+1 454.1.
Synthetic intermediate I-5
By the intermediate compound I -4 and P of 4.54g (10mmol)2O5It is dissolved in the POCl of 60mL3, and stirred at a temperature of 105 DEG C 24 hours.After the completion of reaction, solvent is removed, and neutralization technique is carried out to it using NaOH.Then, by using ethyl acetate pair It carries out extraction process.By using the organic layer that magnesium sulfate drying is obtained by it.By the remnants obtained from its evaporation solvent Thing is isolated and purified by silica gel column chromatography, to obtain the intermediate compound I -5 of 2.75g (63% yield).The chemical combination for being obtained Thing is identified through LC-MS.C25H14BrN3:M+1 436.0.
Synthetic intermediate I-6
To synthesize intermediate compound I -6 of 3.43g (71% yield) with synthetic intermediate I-1 identical modes, except using Intermediate compound I -5 replaces 5- bromo -1,10- phenanthroline.The compound for being obtained is identified through LC-MS.C31H26BN3O2:M+1 484.2.
Synthesis compound 2
By the intermediate compound I -6 of 4.83g (10mmol), the 2- chloro -4,6- diphenyl -1,3,5- three of 2.68g (10mmol) Tetrakis triphenylphosphine palladium (Pd (the PPh of piperazine, 0.58g (0.5mmol)3)4) and 4.14g (30mmol) K2CO3It is dissolved in 60mL's THF/H2In O (2/1 volume ratio) mixed solution, then stirred 16 hours at a temperature of 80 DEG C.Reaction solution is cooled to Room temperature, is then added to the water of 40mL, and three extraction process are carried out to it by using the diethyl ether of 50mL.By using sulphur Sour magnesium dries the organic layer collected, and then, is separated by silica gel column chromatography by the residue obtained from its evaporation solvent Purifying, to obtain the compound 2 of 4.53g (77% yield).Through MS/FAB and1H NMR identify obtained compound. C40H24N6Calculated value 588.21, measured value 588.22.
1H NMR(CDCl3,400MHz)δ9.47-9.45(m,1H),9.29-9.27(m,1H),9.08-9.07(dd,1H), 9.00-8.99(dd,1H),8.82-8.78(m,6H),8.61-8.58(m,3H),8.32-8.30(m,1H),7.91-7.85(m, 2H),7.63-7.53(m,6H),7.42-7.38(m,2H)
[synthesis example 2:Synthesis compound 8]
To synthesize the compound 8 of 4.13g (74% yield) with the synthesis identical mode of compound 2, except using respectively Intermediate compound I -5 and pyrene -1- boric acid replace intermediate compound I -6 and 2- chloro -4,6- diphenyl -1,3,5- triazines.Through MS/FAB and1H NMR identifies obtained compound.C41H23N3Calculated value 557.19, measured value 557.20.
1H NMR(CDCl3,400MHz)δ9.47-9.45(m,1H),9.30-9.28(m,1H),9.07-9.06(dd,1H), 9.01-9.00(dd,1H),8.60-8.58(m,1H),8.39-8.30(m,3H),8.14-7.98(m,7H),7.91-7.84(m, 5H),7.58-7.53(m,3H).
[synthesis example 3:Synthesis compound 33]
Synthetic intermediate I-7
To synthesize intermediate compound I -7 of 3.31g (73% yield) with synthetic intermediate I-4 identical modes, except using 3- bromo-benzoyl chlorides replace 4- bromo-benzoyl chlorides.The compound for being obtained is identified through LC-MS.C25H16BrN3O:M+1 454.1
Synthetic intermediate I-8
Synthesize 3.05g (70% yield) intermediate compound I -8 with synthetic intermediate I-5 identical modes, except in use Mesosome I-7 replaces intermediate compound I -4.The compound for being obtained is identified through LC-MS.C25H14Br N3:M+1 436.0
Synthesis compound 33
To synthesize the compound 33 of 4.43g (71% yield) with the synthesis identical mode of compound 2, except using respectively Intermediate compound I -8 and intermediate A -1 replace intermediate compound I -6 and 2- chloro -4,6- diphenyl -1,3,5- triazines.Through MS/FAB and1H NMR identifies obtained compound.C44H25N5Calculated value 623.21, measured value 623.23
1H NMR(CDCl3,400MHz)δ9.46-9.44(m,1H),9.27-9.25(m,1H),9.08-9.07(dd,1H), 9.01-9.00(dd,1H),8.70-8.69(m,1H),8.60-8.58(m,1H),8.32-8.28(m,3H),8.04-8.02(m, 1H),7.91-7.81(m,4H),7.70-7.47(m,8H),7.43-7.25(m,3H)
[synthesis example 4:Synthesis compound 64]
Synthetic intermediate I-9
To synthesize intermediate compound I -9 of 2.47g (65% yield) with synthetic intermediate I-2 identical modes, except using Bromo -2- the nitrobenzene of 1,4- bis- replaces 1- bromo -2- nitrobenzene.The compound for being obtained is identified through LC-MS.C18H10BrN3O2:M +1 380.0
Synthetic intermediate I-10
To synthesize intermediate compound I -10 of 3.26g (93% yield) with synthetic intermediate I-3 identical modes, except using Intermediate compound I -9 replaces intermediate compound I -2.The compound for being obtained is identified through LC-MS.C18H12BrN3:M+1 350.0
Synthetic intermediate I-11
To synthesize intermediate compound I -11 of 3.53g (78% yield) with synthetic intermediate I-4 identical modes, except respectively Replace intermediate compound I -3 and 4- bromo-benzoyl chlorides using intermediate compound I -10 and benzaldehyde.The compound for being obtained is identified through LC-MS. C25H16BrN3O:M+1 454.1
Synthetic intermediate I-12
To synthesize intermediate compound I -12 of 2.84g (65% yield) with synthetic intermediate I-5 identical modes, except using Intermediate compound I -11 replaces intermediate compound I -4.The compound for being obtained is identified through LC-MS.C25H14BrN3:M+1 436.0.
Synthesis compound 64
To synthesize the compound 64 of 4.37g (70% yield) with the synthesis identical mode of compound 2, except using respectively Intermediate compound I -12 and intermediate A -1 replace intermediate compound I -6 and 2- chloro -4,6- diphenyl -1,3,5- triazines.Through MS/FAB and1H NMR identifies obtained compound.C44H25N5Calculated value 623.21, measured value 623.20.
1H NMR(CDCl3,400MHz)δ9.50-9.47(m,1H),9.29-9.27(m,1H),9.08-9.07(dd,1H), 9.00-8.99(dd,1H),8.80-8.78(m,1H),8.42-8.41(m,1H),8.32-8.31(m,1H),8.24-8.20(m, 2H),8.05-8.00(m,2H),7.91-7.88(m,1H),7.76-7.73(m,1H),7.68-7.64(m,4H),7.58-7.56 (m,1H),7.51-7.46(m,4H),7.34-7.23(m,3H)
[synthesis example 5:Synthesis compound 83]
Synthetic intermediate I-13
To synthesize intermediate compound I -13 of 3.43g (71% yield) with synthetic intermediate I-1 identical modes, except using Intermediate compound I -12 replaces 5- bromo -1,10- phenanthroline.The compound for being obtained is identified through LC-MS.C31H26BN3O2:M+1 484.2
Synthetic intermediate I-14
To synthesize intermediate compound I -14 of 3.48g (68% yield) with the synthesis identical mode of compound 2, except making respectively Replace intermediate compound I -6 and 2- chloro -4,6- diphenyl -1,3,5- triazines with intermediate compound I -13 and 1,3- dibromo-benzenes.Obtained Compound through LC-MS identify.C31H18BrN3:M+1 512.1
Synthesis compound 83
The intermediate compound I -14 of 5.12g (10mmol) is dissolved in the THF of 100mL, and is added at a temperature of -78 DEG C The n-BuLi of 4mL (2.5M is in hexane).After one hour, the Chlorodiphenylphosphine of 2.20g (10mmol) is slowly added dropwise to it. Stirring gained mixture 3 hours, is then heated to room temperature.Then, water is added to, by using the ethyl acetate of 30mL to it It is rinsed technique three times.Ethyl acetate layer after rinsing is by using MgSO4It is dried, and is dried under reduced pressure to obtain Obtain intermediate compound I -7.Intermediate compound I -7 is dissolved in the dichloromethane of 40mL, and is added to the hydrogen peroxide of 4mL.Then, in room temperature Lower stirring reaction solution 20 hours.It is added to the water of 20mL, and dichloromethane by using 20mL carries out extraction work to it Skill three times.The organic layer collected is dried by using magnesium sulfate, then, silicon is passed through by the residue obtained from its evaporation solvent Glue column chromatography separating purification, to obtain the compound 83 of 4.12g (65% yield).Through MS/FAB and1H NMR identifications are obtained Compound.C43H28N3OP calculated values 633.20, measured value 633.22
1H NMR(CDCl3,400MHz)δ9.51-9.46(m,1H),9.30-9.27(m,1H),9.08-9.07(dd,1H), 9.00-8.99(dd,1H),8.47-8.45(m,1H),8.22-8.21(m,1H),8.09-8.06(m,1H),8.04-8.00(m, 2H),7.91-7.88(m,2H),7.82-7.79(m,1H),7.68-7.64(m,7H),7.59-7.46(m,5H),7.44-7.40 (m,4H)
[synthesis example 6:Synthesis compound 90]
Synthetic intermediate I-15
To synthesize intermediate compound I -15 of 3.33g (65% yield) with the synthesis identical mode of compound 2, except making respectively Replace intermediate compound I -6 and 2- chloro -4,6- diphenyl -1,3,5- triazines with intermediate compound I -13 and 1,4- dibromo-benzenes.Obtained Compound through LC-MS identify.C31H18BrN3:M+1 512.1.
Synthetic intermediate I-16
To synthesize intermediate compound I -16 of 4.31g (77% yield) with synthetic intermediate I-1 identical modes, except using Intermediate compound I -15 replaces 5- bromo -1,10- phenanthroline.The compound for being obtained is identified through LC-MS.C37H30BN3O2:M+1 560.2
Synthesis compound 90
To synthesize the compound 64 of 4.03g (66% yield) with the synthesis identical mode of compound 2, except using respectively Intermediate compound I -16 and intermediate A -2 replace intermediate compound I -6 and 2- chloro -4,6- diphenyl -1,3,5- triazines.Through MS/FAB and1H NMR identifies obtained compound.C44H26N4Calculated value 610.22, measured value 610.21.
1H NMR(CDCl3,400MHz)δ9.50-9.46(m,1H),9.29-9.27(m,1H),9.09-9.08(dd,1H), 9.00-8.99(dd,1H),8.79-8.77(m,1H),8.68-8.66(m,1H),8.58-8.56(m,1H),8.30-8.27(m, 3H),8.16-8.14(m,2H),8.04-7.81(m,8H),7.74-7.70(m,1H),7.66-7.55(m,5H).
Embodiment 1
By will thereon deposit thickness for 15 Ω/cm2 ITO layer ito glass substrate (healthy and free from worry manufacture) Cut into the size of 50mm × 50mm × 0.7mm to prepare anode, it is each to be cleaned by ultrasonic ito glass substrate using isopropanol and pure water 5 minutes, then make ito glass substrate exposed to ultraviolet irradiation and ozone 30 minutes, to clean ito glass substrate.Then will Ito glass substrate is arranged on vacuum deposition device.
Known materials 2-TNATA vacuum moulding machines are had on ito glass substrate (anode) with formationThickness Hole injection layer, then vacuum moulding machine 4, double [N- (1- naphthyls)-N- phenylaminos] biphenyl (the hereinafter referred to as NPB, as hole of 4'- The known materials of transport compound) have with formationThe hole transmission layer of thickness.
With 98:2 weight ratio will be as bis--naphthalenes of compound 9,10- -2- bases-anthracene known to blue-fluorescence main body (referred to hereinafter as It is ADN) and as double [2- (4- (N, the N- diphenyl amino) phenyl) ethene of compound 4,4'- known to blue-fluorescence dopant Base] biphenyl (hereinafter referred to as DPAVBi) be co-deposited on hole transmission layer, so as to formed haveThickness luminescent layer.
Then, will be deposited on luminescent layer according to the compound 2 of one or more implementation methods has with formation The electron transfer layer of thickness.LiF (it is alkali halide) depositions are had with formation on the electron transport layerThickness Electron injecting layer, then, by Al vacuum moulding machines thereon with formed haveLiF/Al electrodes (the negative electrode electricity of thickness Pole), so as to complete the manufacture of organic light emitting apparatus.
Embodiment 2
The organic light emitting apparatus of embodiment 2 are manufactured in the same manner as example 1, except when electron transfer layer is formed Replace compound 2 using compound 8.
Embodiment 3
The organic light emitting apparatus of embodiment 3 are manufactured in the same manner as example 1, except when electron transfer layer is formed Replace compound 2 using compound 33.
Embodiment 4
The organic light emitting apparatus of embodiment 4 are manufactured in the same manner as example 1, except when electron transfer layer is formed Replace compound 2 using compound 64.
Embodiment 5
The organic light emitting apparatus of embodiment 5 are manufactured in the same manner as example 1, except when electron transfer layer is formed Replace compound 2 using compound 83.
Embodiment 6
The organic light emitting apparatus of embodiment 6 are manufactured in the same manner as example 1, except when electron transfer layer is formed Replace compound 2 using compound 90.
Comparative example 1
The organic light emitting apparatus of comparative example 1 are manufactured in the same manner as example 1, except when electron transfer layer is formed Use known compound Alq3Instead of compound 2.
The organic light emitting apparatus of comparative example 1 are in 50mA/cm2Current density under show driving voltage, 2 of 7.35V, 065cd/m2Brightness, the luminous efficiency of 4.13cd/A and 145@100mA/cm2Half-life.
The result of embodiment 1 to 6 and comparative example 1 is displayed in table 1.
[table 1]
Compared with comparative example 1, when the compound of the structure with formula 1 according to one or more implementation methods is used as electricity During sub- transmission material, all compounds have the driving voltage for reducing 1V or more, show with the efficiency for quite improving Excellent I-V-L characteristics, especially, show excellent lifetime improving effect.Be can be seen that according to one by these results Or the compound of multiple implementation methods is suitable as electron transport material.
Organic light emitting apparatus according to one or more implementation methods can have high efficiency, low driving voltage, high brightness and Long-life.
Although concept of the present invention is particularly shown and described with reference to its illustrative embodiments, it should be appreciated that, In the case of the spirit and scope limited in without departing substantially from such as claims, those of ordinary skill in the art can make wherein each Plant the change in form and in details.

Claims (20)

1. a kind of compound represented by formula 1：
<Formula 1>
Wherein, in formula 1,
R1And R2It is each independently selected from hydrogen, deuterium, halogen, nitro, cyano group, substituted or unsubstituted C1-C60Alkyl, substitution or not Substituted C2-C60Alkenyl, substituted or unsubstituted C2-C60Alkynyl, substituted or unsubstituted C1-C60Alkoxy, substitution do not take The C in generation3-C10Cycloalkyl, substituted or unsubstituted C1-C10Heterocyclylalkyl, substituted or unsubstituted C3-C10Cycloalkenyl group, substitution or Unsubstituted C1-C10Heterocycloalkenyl, substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C6-C60Aryloxy group, substitution Or unsubstituted C6-C60Arylthio, substituted or unsubstituted C1-C60Heteroaryl, it is substituted or unsubstituted unit price it is non-aromatic thick Close polycyclic moiety, substituted or unsubstituted the non-aromatic of unit price and condense miscellaneous polycyclic moiety ,-P (=O) R3R4,-P (=S) R5R6、-S (=O)2R7With-S (=O) R8R9,
X1To X8It is each independently selected from CR11And N,
Wherein X1To X8At least one of be N,
R3To R9And R11It is each independently selected from substituted or unsubstituted C1-C60Alkyl, substituted or unsubstituted C3-C10Cycloalkyl, Substituted or unsubstituted C1-C10Heterocyclylalkyl, substituted or unsubstituted C6-C60Aryl and substituted or unsubstituted C1-C60Heteroaryl Base,
L1And L2It is each independently selected from substituted or unsubstituted C6-C60Arlydene, substituted or unsubstituted C1-C60Inferior heteroaryl, The non-aromatic fused polycycle group of substituted or unsubstituted divalence and the non-aromatic of substituted or unsubstituted divalence condense miscellaneous polycyclic Group,
A to d is each independently 0 to 3 integer, and
Selected from the substituted C1-C60Alkyl, the substituted C2-C60Alkenyl, the substituted C2-C60Alkynyl, the substitution C1-C60Alkoxy, the substituted C3-C10Cycloalkyl, the substituted C1-C10Heterocyclylalkyl, the substituted C3-C10Ring Alkenyl, the substituted C1-C10Heterocycloalkenyl, the substituted C6-C60Aryl, the substituted C6-C60Aryloxy group, described take The C in generation6-C60Arylthio, the substituted C1-C60It is heteroaryl, the substituted univalent non-aromatic fused polycycle group, described It is substituted univalent non-aromatic to condense miscellaneous polycyclic moiety, the substituted C6-C60Arlydene, the substituted C1-C60Sub- heteroaryl The non-aromatic of base, the non-aromatic fused polycycle group of the substituted divalence and the substituted divalence condenses miscellaneous polycyclic moiety At least one of substitution base substitution base is selected from：
Deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amino, amidino groups, diazanyl, hydrazone group, carboxylic acid group or its salt, sulfonic group or Its salt, phosphate or its salt, C1-C60Alkyl, C2-C60Alkenyl, C2-C60Alkynyl and C1-C60Alkoxy；
Each it is selected from the C of at least one of the following substitution1-C60Alkyl, C2-C60Alkenyl, C2-C60Alkynyl and C1-C60Alcoxyl Base：Deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amino, amidino groups, diazanyl, hydrazone group, carboxylic acid group or its salt, sulfonic group or Its salt, phosphate or its salt, C3-C10Cycloalkyl, C1-C10Heterocyclylalkyl, C3-C10Cycloalkenyl group, C1-C10Heterocycloalkenyl, C6-C60Virtue Base, C6-C60Aryloxy group, C6-C60Arylthio, C1-C60Heteroaryl, unit price non-aromatic fused polycycle group, unit price it is non-aromatic Condense miscellaneous polycyclic moiety ,-N (Q11)(Q12)、-Si(Q13)(Q14)(Q15) and-B (Q16)(Q17)；
C3-C10Cycloalkyl, C1-C10Heterocyclylalkyl, C3-C10Cycloalkenyl group, C1-C10Heterocycloalkenyl, C6-C60Aryl, C6-C60Fragrant oxygen Base, C6-C60Arylthio, C1-C60Heteroaryl, the non-aromatic fused polycycle group of unit price and the non-aromatic of unit price condense miscellaneous many ring groups Group；And
Each it is selected from the C of at least one of the following substitution3-C10Cycloalkyl, C1-C10Heterocyclylalkyl, C3-C10Cycloalkenyl group, C1- C10Heterocycloalkenyl, C6-C60Aryl, C6-C60Aryloxy group, C6-C60Arylthio, C1-C60The non-aromatic fused polycycle of heteroaryl, unit price Group and the non-aromatic of unit price condense miscellaneous polycyclic moiety：Deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amino, amidino groups, hydrazine Base, hydrazone group, carboxylic acid group or its salt, sulfonic group or its salt, phosphate or its salt, C1-C60Alkyl, C2-C60Alkenyl, C2-C60Alkynyl, C1-C60Alkoxy, C3-C10Cycloalkyl, C1-C10Heterocyclylalkyl, C3-C10Cycloalkenyl group, C1-C10Heterocycloalkenyl, C6-C60Aryl, C6- C60Aryloxy group, C6-C60Arylthio, C1-C60Heteroaryl, unit price non-aromatic fused polycycle group, unit price it is non-aromatic condense it is miscellaneous Polycyclic moiety ,-N (Q21)(Q22)、-Si(Q23)(Q24)(Q25) and-B (Q26)(Q27),
Wherein Q11To Q17And Q21To Q27Be each independently selected from hydrogen, deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amino, Amidino groups, diazanyl, hydrazone group, carboxylic acid group or its salt, sulfonic group or its salt, phosphate or its salt, C1-C60Alkyl, C2-C60Alkenyl, C2- C60Alkynyl, C1-C60Alkoxy, C3-C10Cycloalkyl, C1-C10Heterocyclylalkyl, C3-C10Cycloalkenyl group, C1-C10Heterocycloalkenyl, C6-C60 Aryl, C1-C60Heteroaryl, the non-aromatic fused polycycle group of unit price and the non-aromatic of unit price condense miscellaneous polycyclic moiety.
2. compound as claimed in claim 1, wherein R11It is hydrogen or deuterium.
3. compound as claimed in claim 1, wherein a and b is each independently 0 to 2 integer.
4. compound as claimed in claim 1, wherein L1And L2It is each independently selected from by an expression in formula 2a to 2f Compound derives the group for obtaining：
5. compound as claimed in claim 1, wherein R1And R2Independently of one another by selected from an expression in formula 3a to 3j：
Wherein, in formula 3a to 3j,
X is O or S,
H1It is CR21R22、NR23, O or S,
R21To R23And Z1It is each independently selected from hydrogen, deuterium, halogen, cyano group, nitro, hydroxyl, carboxyl, substituted or unsubstituted C1- C20Alkyl, substituted or unsubstituted C6-C20Aryl, substituted or unsubstituted C1-C20Heteroaryl, it is substituted or unsubstituted unit price Non-aromatic fused polycycle group and substituted or unsubstituted the non-aromatic of unit price condense miscellaneous polycyclic moiety,
Work as Z1Quantity be more than or equal to 2 when, two or more Z1It is same to each other or different to each other,
P in formula 3a is 1 to 5 integer,
P in formula 3b is 1 to 4 integer,
P in formula 3c is 1 to 4 integer,
P in formula 3d is 1 to 9 integer,
P in formula 3f is 1 to 6 integer,
P in formula 3g is 1 to 7 integer,
P in formula 3h is 1 to 8 integer,
P in formula 3i is 1 to 6 integer,
P in formula 3j is 1 to 7 integer, and
* the binding site with adjacent atom is represented.
6. compound as claimed in claim 1, wherein
The formula 2 represented by formula 1 is represented：
<Formula 2>
R wherein in formula 21、R2、X1To X8、L2, a to d it is identical with defined in formula 1.
7. compound as claimed in claim 1, wherein the formula 3 represented by formula 1 is represented：
<Formula 3>
R wherein in formula 31、R2、L1、L2, a to d it is identical with defined in formula 1.
8. compound as claimed in claim 1, wherein the compound represented by formula 1 is selected from compound 1 to 99 One：
9. a kind of organic light emitting apparatus, including：
First electrode；
Towards the second electrode of the first electrode；And
Organic layer between the first electrode and the second electrode, the organic layer includes luminescent layer,
Wherein described organic layer includes the compound as described in any one of claim 1 to 8.
10. organic light emitting apparatus as claimed in claim 9, wherein the first electrode is anode,
The second electrode is negative electrode, and
The organic layer is further included：
I) the hole transport area between the first electrode and the luminescent layer, the hole transport area includes hole transport At least one of layer, hole injection layer and electronic barrier layer；And
Ii) the electric transmission area between the luminescent layer and the second electrode, the electric transmission area includes electric transmission At least one of layer, hole blocking layer and electron injecting layer.
11. organic light emitting apparatus as claimed in claim 10, wherein the electric transmission area includes such as claim 1 to 8 times Compound described in one.
12. organic light emitting apparatus as claimed in claim 11, wherein the electron transfer layer includes such as claim 1 to 8 times Compound described in one.
13. organic light emitting apparatus as claimed in claim 11, wherein the hole transport area includes charge generating material.
14. organic light emitting apparatus as claimed in claim 13, wherein the charge generating material is p-doping agent.
15. organic light emitting apparatus as claimed in claim 13, wherein the charge generating material is selected from quinone derivative, metal At least one in the compound of oxide and cyano-containing.
16. organic light emitting apparatus as claimed in claim 13, wherein the charge generating material be selected from compound HT-D1 and One kind in F4-TCNQ：
17. organic light emitting apparatus as claimed in claim 10, wherein the electric transmission area includes the material containing metal.
18. organic light emitting apparatus as claimed in claim 10, wherein the electric transmission area includes Li complex compounds.
19. organic light emitting apparatus as claimed in claim 10, wherein the electric transmission area include selected from compound ET-D1 and One kind in ET-D2：
A kind of 20. display devices of the organic light emitting apparatus including as described in any one of claim 9 to 19,
The first electrode of wherein described organic light emitting apparatus is electrically connected with the source electrode of thin film transistor (TFT) or drain electrode.
CN201611243743.7A 2015-12-29 2016-12-29 Compound, organic light emitting apparatus and display device including the compound Pending CN106928223A (en)

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