CN107188883A - A kind of compound applied to OLED fields - Google Patents

A kind of compound applied to OLED fields Download PDF

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Publication number
CN107188883A
CN107188883A CN201610147364.1A CN201610147364A CN107188883A CN 107188883 A CN107188883 A CN 107188883A CN 201610147364 A CN201610147364 A CN 201610147364A CN 107188883 A CN107188883 A CN 107188883A
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Prior art keywords
oled
compound
layer
main part
application example
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CN201610147364.1A
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Inventor
杨红领
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EverDisplay Optronics Shanghai Co Ltd
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EverDisplay Optronics Shanghai Co Ltd
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Priority to CN201610147364.1A priority Critical patent/CN107188883A/en
Publication of CN107188883A publication Critical patent/CN107188883A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms

Abstract

The invention provides a kind of compound applied to OLED fields, its structure is as shown in logical formula (I)：Wherein, R1And R2Separately it is selected from phenolic compound group.The compound is used in OLED material, and be further used in OLED electron transfer layer, luminescent layer and hole transmission layer, more prominent is specifically in OLED feux rouges material of main part, OLED green glows material of main part and OLED hole mobile materials, a kind of OLED containing compound described above finally given, with substantially good performance advantage.

Description

A kind of compound applied to OLED fields
Technical field
The present invention relates to field of organic electroluminescence, more particularly to OLED fields, specially one kind is applied to The compound in OLED fields.
Background technology
TFT-LCD, as a kind of display screen, is a kind of display of non-spontaneous light, it is necessary to thrown through backlight Penetrate light, sequentially penetrate Polarizer in TFT-LCD panels, glass substrate, liquid crystal layer, colored filter, The correlation spare part such as glass substrate, Polarizer, finally enters the eye imaging of people, reaches the function of display. In practical application, TFT-LCD display screens have the shortcomings that slow reaction rate, power consumption, narrow viewing angle, are not enough to As perfect display screen.
OLED, as a kind of new Display Technique, with self luminous characteristic, using very thin organic material Material coating and glass substrate are prepared.When have electric current by when, these organic materials will light.At present, The structure of OLED basic structure such as sandwich, total layer includes hole transmission layer (HTL), lighted Layer (EL) and electron transfer layer (ETL).When supplying power to appropriate voltage, positive pole hole and negative electrode electric charge are just It can be combined in luminescent layer, produce light, be formulated different generation red, green and blue three primary colors according to it, constitute basic Color.Because OLED characteristic is that oneself lights, therefore, visibility and brightness are high, next to that voltage Demand is low and power saving efficiency is high, adds fast, the lightweight, thickness of thin of reaction, and simple structure, cost is low, quilt It is considered as one of product of 21 century most future.
Although OLED has the advantage of each side relative to other displays, in fact, its display, High performance material is a lack of there are still deficiency in terms of life-span, use, one of the reason for important, therefore, Design and the compound or material applied to OLED fields of synthesizing new are those skilled in the art's research works The emphasis of work.
The content of the invention
Based on above-mentioned background, the invention provides a kind of new compound applied to OLED fields, its For in OLED material, and it is further used for OLED electron transfer layer, luminescent layer and hole transmission layer In, more prominent is specifically in feux rouges material of main part, green glow material of main part and hole mobile material, finally Obtained a kind of OLED containing compound described above, with substantially good performance advantage.
The theme of the first aspect of the present invention is a kind of compound applied to OLED fields, it is characterised in that Its structure is as shown in logical formula (I)：
Wherein, R1And R2Separately it is selected from phenolic compound group.
In one embodiment of the invention, the R1And R2For the armaticity chemical combination containing 3-20 carbon or nitrogen Thing group.
Preferably, the R1And R2In contain phenyl ring, naphthalene nucleus or heterocycle structure.
It is highly preferred that the R1And R2Separately it is selected from following structural formula：
In a preferred embodiment of the invention, the compound is selected from following structure：
The theme of the second aspect of the present invention is a kind of material for including compound described above.
The theme of the third aspect of the present invention is a kind of application of compound described above, is included in OLED empty Application in cave transport layer, OLED luminescent layers, OLED electron transfer layers.
Preferably, the compound be applied to OLED feux rouges material of main part, OLED green glows material of main part with And in OLED hole mobile materials.
The theme of the fourth aspect of the present invention is a kind of OLED containing compound described above.
Embodiment
The invention provides a kind of compound applied to OLED fields, it is characterised in that its structure is as led to Shown in formula (I)：
Wherein, R1And R2Separately it is selected from phenolic compound group.
In one embodiment of the invention, the R1And R2For the armaticity chemical combination containing 3-20 carbon or nitrogen Thing group.
In a preferred embodiment, the R1And R2In contain phenyl ring, naphthalene nucleus or heterocycle structure.
In a further preferred embodiment, the R1And R2Separately it is selected from following structural formula：
In a preferred embodiment of the invention, the compound is selected from following structure：
Present invention also offers a kind of material for including compound described above.
Present invention also offers a kind of application of compound described above, be included in OLED hole transmission layers, Application in OLED luminescent layers, OLED electron transfer layers.
In a preferred embodiment, the compound is green applied to OLED feux rouges material of main part, OLED In light material of main part and OLED hole mobile materials.
Present invention also offers a kind of OLED containing compound described above.
With reference to specific embodiment, technical scheme is further explained and illustrated.
Embodiment 1
The synthesis of compound 1：
The preparation method of the compound 1 includes：
0.1mol intermediate As, 0.1mol intermediate Bs and 1000mL dimethyl are added into reaction bulb Formamide, and 0.1mol NaH, under nitrogen protection normal-temperature reaction 12 hours are added thereto；Then, Distilled water terminating reaction is added into reaction solution, and is extracted with ethanol/dichloromethane, salt washing has been separated Machine layer, revolving removes organic solvent, and crude product crosses post, then with dichloromethane and ethyl alcohol recrystallization purifying Compound 1, yield 67%.
Compound 1 is characterized as below：
MS：615.2674
1H-NMR：1.66(6H)7.92(1H)7.87(1H)7.75(1H)7.35(1H)7.41(1H) 7.61(1H)7.28(1H)7.54(4H)7.48(2H)7.32(2H)7.21(1H)7.32(2H) 7.47(2H)7.23(1H)7.35(2H)7.37(2H)7.44(1H)7.64(1H)。
Embodiment 2
The synthesis of compound 2：
The preparation method of the compound 2 includes：
0.1mol intermediate As, 0.1mol intermediates C and 1000mL dimethyl are added into reaction bulb Formamide, and 0.1mol NaH, under nitrogen protection normal-temperature reaction 12 hours are added thereto；Then, Distilled water terminating reaction is added into reaction solution, and is extracted with ethanol/dichloromethane, salt washing has been separated Machine layer, revolving removes organic solvent, and crude product crosses post, then with dichloromethane and ethyl alcohol recrystallization purifying Compound 2, yield 44%.
Compound 2 is characterized as below：
MS：655.2987
1H-NMR：1.64(12H)7.93(2H)7.85(2H)7.72(2H)7.34(2H)7.44(2H) 7.62(2H)7.29(2H)7.32(2H)7.47(2H)7.23(1H)7.35(2H)7.37(2H) 7.63(1H)7.64(1H)。
Embodiment 3
The synthesis of compound 3：
The preparation method of the compound 3 includes：
0.1mol intermediate As, 0.1mol intermediates D and 1000mL dimethyl are added into reaction bulb Formamide, and 0.1mol NaH, under nitrogen protection normal-temperature reaction 12 hours are added thereto；Then, Distilled water terminating reaction is added into reaction solution, and is extracted with ethanol/dichloromethane, salt washing has been separated Machine layer, revolving removes organic solvent, and crude product crosses post, then with dichloromethane and ethyl alcohol recrystallization purifying Compound 3, yield 38%.
Compound 3 is characterized as below：
MS：575.2361
1H-NMR：7.55(8H)7.49(4H)7.31(4H)7.22(2H)7.32(2H)7.47(2H) 7.23(1H)7.35(2H)7.37(2H)7.74(1H)7.73(1H)。
Embodiment 4
The synthesis of compound 4：
The preparation method of the compound 4 includes：
0.1mol intermediate As, 0.1mol intermediate Es and 1000mL dimethyl are added into reaction bulb Formamide, and 0.1mol NaH, under nitrogen protection normal-temperature reaction 12 hours are added thereto；Then, Distilled water terminating reaction is added into reaction solution, and is extracted with ethanol/dichloromethane, salt washing has been separated Machine layer, revolving removes organic solvent, and crude product crosses post, then with dichloromethane and ethyl alcohol recrystallization purifying Compound 4, yield 47%.
Compound 4 is characterized as below：
MS：589.2518
1H-NMR：1.66(6H)7.92(1H)7.87(1H)7.75(1H)7.35(1H)7.41(1H) 7.61(1H)7.28(1H)7.54(1H)7.48(1H)7.32(1H)7.31(2H)7.41(2H) 7.32(2H)7.47(2H)7.23(1H)7.35(2H)7.37(2H)7.73(1H)7.72(1H)。
Application Example --- OLED
Contrast Application Example：
Transparent anode electrode ito substrate is cleaned by ultrasonic 5-10 minutes in isopropanol, and exposed to ultraviolet light Lower 20-30 minutes, then handled 5-10 minutes with plasma.Then the ito substrate after processing is put into Evaporated device.One layer of 30-50nm NPB is deposited first as hole transmission layer, followed by the steaming of luminescent layer Plating, mixing evaporation, CBP, and 2--10% Ir (piq) 3, then evaporation 20-40nm Alq3 conducts Electron transfer layer, is then deposited 0.5-2nmLiF again, and 100-200nm metal Al is finally deposited.
Application Example 1
Transparent anode electrode ito substrate is cleaned by ultrasonic 5-10 minutes in isopropanol, and exposed to ultraviolet light Lower 20-30 minutes, then handled 5-10 minutes with plasma.Then the ito substrate after processing is put into Evaporated device.One layer of 30-50nm NPB is deposited first as hole transmission layer, followed by the steaming of luminescent layer Plating, mixing evaporation compound CBP, and 2--10% Ir (piq) 3, then evaporation 20-40nm chemical combination Thing 1, is then deposited 0.5-2nmLiF again, and 100-200nm metal Al is finally deposited.
Application Example 2
Change the Alq3 in comparative example into compounds 2, be used as electron transfer layer.
Application Example 3
Change the Alq3 in comparative example into compounds 3, be used as electron transfer layer.
Application Example 4
Change the Alq3 in comparative example into compounds 4, be used as electron transfer layer.
Application Example 5
Change the NPB in comparative example into compounds 1, be used as hole transmission layer.
Application Example 6
Change the NPB in comparative example into compounds 3, be used as hole transmission layer.
Application Example 7
Change the CBP in comparative example into compounds 2, be used as luminescent layer.
Application Example 8
Change the CBP in comparative example into compounds 4, be used as luminescent layer.
Wherein：
OLED is produced as follows：
Contrast Application Example：ITO/NPB/CBP：Ir(piq)3/Alq3/LiF/Al；
Application Example 1：ITO/NPB/CBP：The compound 1/LiF/Al of Ir (piq) 3/；
Application Example 2：ITO/NPB/CBP：The compound 2/LiF/Al of Ir (piq) 3/；
Application Example 3：ITO/NPB/CBP：The compound 3/LiF/Al of Ir (piq) 3/；
Application Example 4：ITO/NPB/CBP：The compound 4/LiF/Al of Ir (piq) 3/；
Application Example 5：ITO/ compounds 1/CBP：Ir(piq)3/Alq3/LiF/Al；
Application Example 6：ITO/ compounds 3/CBP：Ir(piq)3/Alq3/LiF/Al；
Application Example 7：ITO/NPB/ compounds 2：Ir(piq)3/Alq3/LiF/Al；
Application Example 8：ITO/NPB/ compounds 4：Ir(piq)3/Alq3/LiF/Al；
Under 1000nits, OLED result is as follows：
Table 1
From upper table 1, compared with contrast Application Example common in the art, using of the present invention Compound prepare OLED needed for driving voltage it is lower, and produce luminous flux it is bigger, therefore tool There are more preferable luminescent properties.
The specific embodiment of the present invention is described in detail above, but it is intended only as example, and the present invention is simultaneously It is not restricted to particular embodiments described above.To those skilled in the art, it is any to present invention progress Equivalent modifications and substitute also all among scope of the invention.Therefore, the spirit and model of the present invention are not being departed from Enclose lower made impartial conversion and change, all should be contained within the scope of the invention.

Claims (9)

1. a kind of compound applied to OLED fields, it is characterised in that its structure is as shown in logical formula (I)：
Wherein, R1And R2Separately it is selected from phenolic compound group.
2. compound according to claim 1, it is characterised in that the R1And R2To contain 3-20 carbon Or the phenolic compound group of nitrogen.
3. compound according to claim 1, it is characterised in that the R1And R2In contain phenyl ring, naphthalene nucleus Or heterocycle structure.
4. compound according to claim 1, it is characterised in that the R1And R2Separately selected from such as Lower structural formula：
5. compound according to claim 1, it is characterised in that the compound is selected from following structure：
6. a kind of material for including compound described in any one in claim 1-5.
7. the application of compound described in any one in a kind of claim 1-5, it is characterised in that be included in OLED Application in hole transmission layer, OLED luminescent layers, OLED electron transfer layers.
8. apply according to claim 7, it is characterised in that the compound is applied to OLED feux rouges main bodys In material, OLED green glows material of main part and OLED hole mobile materials.
9. the OLED of compound described in any one in a kind of 1-5 containing claim.
CN201610147364.1A 2016-03-15 2016-03-15 A kind of compound applied to OLED fields Pending CN107188883A (en)

Priority Applications (1)

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CN201610147364.1A CN107188883A (en) 2016-03-15 2016-03-15 A kind of compound applied to OLED fields

Publications (1)

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CN107188883A true CN107188883A (en) 2017-09-22

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022145365A1 (en) * 2020-12-28 2022-07-07 Jsr株式会社 Semiconductor substrate production method and composition

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140145149A1 (en) * 2012-11-26 2014-05-29 Universal Display Corporation Organic Luminescent Compound With Delayed Fluorescence
KR20150111441A (en) * 2014-03-24 2015-10-06 (주)피엔에이치테크 An electroluminescent compound and an electroluminescent device comprising the same
WO2016012075A1 (en) * 2014-07-21 2016-01-28 Merck Patent Gmbh Materials for electronic devices

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140145149A1 (en) * 2012-11-26 2014-05-29 Universal Display Corporation Organic Luminescent Compound With Delayed Fluorescence
KR20150111441A (en) * 2014-03-24 2015-10-06 (주)피엔에이치테크 An electroluminescent compound and an electroluminescent device comprising the same
WO2016012075A1 (en) * 2014-07-21 2016-01-28 Merck Patent Gmbh Materials for electronic devices

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022145365A1 (en) * 2020-12-28 2022-07-07 Jsr株式会社 Semiconductor substrate production method and composition

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Application publication date: 20170922