CN109206324B - Novel compound and organic light emitting device comprising the same - Google Patents
Novel compound and organic light emitting device comprising the same Download PDFInfo
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- CN109206324B CN109206324B CN201810733996.5A CN201810733996A CN109206324B CN 109206324 B CN109206324 B CN 109206324B CN 201810733996 A CN201810733996 A CN 201810733996A CN 109206324 B CN109206324 B CN 109206324B
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Abstract
The present invention relates to novel arylamine compounds, which, when used as a Hole Transport Layer (HTL), a light emitting auxiliary layer (HT prime), or a Hole Injection Layer (HIL), can increase hole injection and transport characteristics, thereby providing high efficiency and long life effects of devices.
Description
Technical Field
The present invention relates to novel arylamine compounds and organic light emitting devices comprising the same.
Background
In the organic light emitting diode, materials used as the organic layer may be broadly classified into a light emitting material, a hole injecting material, a hole transporting material, an electron injecting material, and the like according to functions. The luminescent materials are classified into high-molecular and low-molecular materials according to molecular weight, and into fluorescent materials in a singlet excited state derived from electrons and phosphorescent materials in a triplet excited state derived from electrons according to luminescence mechanism, and the luminescent materials are classified into blue, green, and red luminescent materials and yellow and orange luminescent materials required to exhibit better natural colors according to luminescence colors. Also, in order to increase color purity and increase luminous efficiency by energy transfer, a host/dopant species may be used as a light-emitting substance. The principle is that when a dopant having a small energy band gap and excellent light emission efficiency as compared with a host mainly constituting a light emitting layer is mixed in a small amount in an auxiliary layer, excitons generated in the host are transported to the dopant, and light having high efficiency is emitted. At this time, the wavelength of the host shifts to the wavelength band of the dopant, and thus light of a desired wavelength can be obtained according to the type of the dopant and the host used.
As a substance used for such an organic light-emitting device, various compounds have been known, but in the case of an organic light-emitting device using a substance known so far, development of a new material is continuously required due to a high driving voltage, low efficiency and short lifetime. Accordingly, there is a continuous effort to develop an organic light emitting device having low voltage driving, high luminance and long life using a substance having excellent characteristics.
Prior art literature
Patent literature
Japanese laid-open patent 10-2015-530735
Disclosure of Invention
The present invention provides novel compounds and organic light emitting devices comprising the same.
However, the problems to be solved by the present invention are not limited to the above-described problems, and other problems not described can be clearly understood by those skilled in the art to which the present invention pertains from the following descriptions.
The first embodiment of the present invention provides a compound represented by the following chemical formula 1.
Chemical formula 1
In the above-mentioned chemical formula 1,
Ar 1 to Ar 4 are each independently a substituted or unsubstituted C 6～C30 aryl group or a substituted or unsubstituted C 5～C30 heteroaryl group,
Ar 5 is substituted or unsubstituted aryl of C 6～C10,
R, R', R 1 and R 2 are each independently hydrogen, substituted or unsubstituted C 1～C30 alkyl, substituted or unsubstituted C 2～C30 alkenyl, substituted or unsubstituted C 6～C30 aryl, or substituted or unsubstituted C 5～C30 heteroaryl,
L is 0 or an integer from 1 to 4, m is 0 or an integer from 1 to 3.
The second embodiment of the present invention provides an organic light emitting device comprising the compound of the present invention.
The present invention relates to a novel compound of arylamine having fluorene structure and linear aryl group introduced therein, and more particularly, to a novel compound having fluorene structure and linear aryl group directly bonded to nitrogen, wherein electrons are easily blocked by forming deep HOMO and high LUMO, and the conjugated and molecular thin film alignment is improved by enlarging the number of linear connected aryl groups of 4 or more, thereby enabling to suppress the roll-off phenomenon and to realize a long-life device by rapid hole mobility (hole mobility). Further, the other aryl group of the aryl amine is fixed to an aryl group having not more than C 10 instead of the linear aryl group, so that an exciton is efficiently formed in the light-emitting layer while maintaining appropriate HOMO and LUMO and high T1, thereby realizing a high-efficiency organic light-emitting device. Also, since 4 or more aryl groups are linearly linked, the Tg is high even at a small molecular weight, thereby preventing recrystallization at the time of driving, and driving stability of the device can be increased.
When the compound of the present invention is used as a Hole Transport Layer (HTL), a light emitting auxiliary layer (HT prime), or a Hole Injection Layer (HIL), hole injection and transport characteristics can be increased, thereby providing high efficiency and long life effects of the device. The compound of the present invention can maintain high triplet energy and thus exhibit high efficiency, and can maintain high Tg due to substituents composed of 4 or more linear aryl groups, thereby exhibiting thin film stability and long life effect when driving a device.
The compound of the present invention has high luminous efficiency, improved driving voltage and long life, and is suitable for use in organic light emitting device, solar power generating organic light device, etc. and may be used in flexible display, illuminator, etc. and has great contribution to the Organic Light Emitting Diode (OLED) industry.
Drawings
Fig. 1 shows a schematic view of an organic light emitting device according to an example of the present invention.
Description of the reference numerals
100: Substrate board
200: Hole injection layer
300: Hole transport layer
400: Light-emitting layer
500: Electron transport layer
600: Electron injection layer
1000: Anode
2000: Cathode electrode
Detailed Description
Hereinafter, examples and embodiments of the present invention will be described in detail with reference to the accompanying drawings so that those skilled in the art to which the present invention pertains can easily implement the present invention.
The invention may be embodied in many different forms and is not limited to the examples and embodiments described herein. In the drawings, for the purpose of clearly explaining the present invention, parts irrelevant to the explanation are omitted, and like reference numerals are given to like parts throughout the specification.
Throughout the present specification, when one element is located "on" another element, it includes not only the case where one element is in contact with another element but also the case where another element exists between two elements.
Throughout the specification, when a portion "comprises" a structural element, unless specifically stated to the contrary, it is meant that other structural elements may also be included, rather than excluded. The terms "about," "substantially," and the like as used throughout the present specification are used in their numerical or near-numerical meanings when referring to manufacturing and material tolerances, to prevent an ill-minded infringer from improperly utilizing the disclosure of the exact or absolute numerical values mentioned to aid in understanding the present invention. The term "to (a) step" or "a step of" as used throughout the specification of the present invention does not mean "a step of".
Throughout the present specification, the term "combination thereof" included in Markush (Markush) -type expression means a mixture or combination of one or more selected from the group consisting of a plurality of structural elements described in Markush-type expression, and means that one or more selected from the group consisting of the plurality of structural elements is included.
Throughout the present specification, the expression "a and/or B" means "a or B, or a and B".
Throughout the present specification, the term "aryl" means an aromatic hydrocarbon ring group containing C 6-30, for example, phenyl, benzyl, naphthyl, biphenyl, terphenyl, fluorenyl, phenanthryl, triphenylenyl, phenylalkenyl,Radicals, fluoran thiophenemethyl radicals, benzofluorenyl radicals, benzotriphenylenyl radicals, and benzosThe "heteroaryl" as an aromatic ring of C 5-30 containing at least one hetero element means, for example, an aromatic ring containing a group selected from the group consisting of pyrrolinyl, pyrazinyl, pyridyl, indolyl, isoindolyl, furyl, benzofuryl, isobenzofuryl, dibenzofuranyl, benzothienyl, dibenzothiophenyl, quinolinyl, isoquinolinyl, quinoxalinyl, carbazolyl, phenanthrene cry, acridinyl, phenanthrolinyl, thienyl and an aromatic heterocyclic group formed by a pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, indole ring, quinoline ring, acridine ring, pyrrolidine ring, dioxane ring, piperidine ring, morpholine ring, piperazine ring, carbazole ring, furan ring, thiophene ring, oxazole ring, oxadiazole ring, benzoxazole ring, thiazole ring, thiadiazole ring, benzothiazole ring, triazole ring, imidazole ring, benzimidazole ring, pyran ring, dibenzofuran ring, and the like.
Throughout the present specification, the term "alkyl" may comprise a linear or branched saturated or unsaturated C 1-C6 alkyl group, for example, may comprise methyl, ethyl, propyl, butyl, pentyl, hexyl or all isomers thereof, but may not be limited thereto.
Throughout the present specification, the term "substituted or unsubstituted" means substituted or unsubstituted with one or more groups selected from the group consisting of heavy hydrogen, halogen, amino, nitrile, nitro, silane, alkyl or C 1～C20 alkyl, alkenyl or C 2～C20 alkenyl, alkoxy or C 1～C20 alkoxy, cycloalkyl or C 3～C20 cycloalkyl, heterocycloalkyl or C 3～C20 heterocycloalkyl or C 5～C30 aryl or C 5～C30 heteroaryl.
Also, throughout the specification of the present invention, the same reference numerals may have the same meaning unless specifically mentioned.
Throughout the present specification, the term "fluorene" may include the case where the hydrogen bound to carbon 9 is substituted with a substituted or unsubstituted alkyl group of C 1-20, a substituted or unsubstituted alkenyl group of C 1-20, a substituted or unsubstituted aryl group of C 5-30, or a substituted or unsubstituted heteroaryl group of C 3-30.
The first embodiment of the present invention provides a compound represented by the following chemical formula 1:
Chemical formula 1
Ar 1 to Ar 4 are each independently a substituted or unsubstituted C 6～C30 aryl group or a substituted or unsubstituted C 5～C30 heteroaryl group,
Ar 5 is substituted or unsubstituted aryl of C 6～C10,
R, R', R 1 and R 2 are each independently hydrogen, substituted or unsubstituted C 1～C30 alkyl, substituted or unsubstituted C 2～C30 alkenyl, substituted or unsubstituted C 6～C30 aryl, or substituted or unsubstituted C 5～C30 heteroaryl,
L is 0 or an integer from 1 to 4, m is 0 or an integer from 1 to 3.
In one embodiment of the present invention, ar 1 to Ar 4 may be phenyl, naphthyl or phenanthryl.
In one example of the present invention, the substituent represented by-Ar 1-Ar2-Ar3-Ar4 in chemical formula 1 may have more than one meta (meta) or ortho (ortho) bond.
In one embodiment of the present invention, ar 5 may be phenyl or naphthyl.
Also, in an example of the present invention, each of Ar 1 to Ar 4 may be independently a phenyl group, a naphthyl group or a phenanthryl group, and Ar 5 may be a phenyl group or a naphthyl group.
In one embodiment of the present invention, each of R and R' may be independently methyl or phenyl.
In one embodiment of the present invention, R 1 and R 2 may be hydrogen or phenyl.
In one example of the present invention, the above compound may be represented by the following chemical formula 2:
Chemical formula 2
In the above-mentioned chemical formula 2,
Ar 1 to Ar 4、R、R`、R1、R2, l and m are as defined in formula 1 above,
R 3 is hydrogen, substituted or unsubstituted C 1～C30 alkyl, or substituted or unsubstituted C 2～C30 alkenyl,
N is 0 or an integer from 1 to 5.
In one example of the present invention, the above compound may be represented by the following chemical formula 3:
Chemical formula 3
In the chemical formula 3 described above, the chemical formula,
Ar 4、R1、R2, l and m are as defined in formula 1 above,
R 3 is hydrogen, substituted or unsubstituted C 1～C30 alkyl, or substituted or unsubstituted C 2～C30 alkenyl,
N is 0 or an integer from 1 to 5,
Ar and Ar' are each independently a substituted or unsubstituted aryl group of C 6～C30,
R 6 to R 8 are each independently hydrogen, substituted or unsubstituted C 1～C30 alkyl, substituted or unsubstituted C 2～C30 alkenyl, substituted or unsubstituted C 6～C30 aryl, or substituted or unsubstituted C 5～C30 heteroaryl.
In one example of the present invention, the above compound may be represented by the following chemical formula 4:
Chemical formula 4
In the chemical formula 4 described above, the chemical formula,
R 1、R2, l and m are as defined in formula 1 above,
R 3 is hydrogen, substituted or unsubstituted C 1～C30 alkyl, or substituted or unsubstituted C 2～C30 alkenyl,
N is 0 or an integer from 1 to 5,
R 4 and R 5 are each independently hydrogen, substituted or unsubstituted C 1～C30 alkyl, substituted or unsubstituted C 2～C30 alkenyl, substituted or unsubstituted C 6～C30 aryl, or substituted or unsubstituted C 5～C30 heteroaryl,
R 6 to R 9 are each independently hydrogen, substituted or unsubstituted C 1～C30 alkyl, substituted or unsubstituted C 2～C30 alkenyl, substituted or unsubstituted C 6～C30 aryl, or substituted or unsubstituted C 5～C30 heteroaryl.
In one example of the invention, R 3 may be hydrogen or, alternatively, n may be 0.
In one embodiment of the present invention, R 4 to R 9 may be hydrogen.
In one example of the present invention, the compound represented by the above chemical formula 1 may be synthesized according to the reaction of the following chemical formula 1, but may not be limited thereto:
Reaction 1
In the above-mentioned reaction scheme, the reaction mixture,
Ar 1 to Ar 5、R、R`、R1、R2, l and m are as defined in formula 1 above.
In an example of the present invention, the compound represented by the above chemical formula 1 may include the following compounds, but is likely to be limited thereto:
For example, the compound represented by the above chemical formula 1 may include a compound that minimizes a condensation group, thereby maintaining a higher T1 and maximizing an exciton confinement effect in the light emitting layer:
the second embodiment of the present invention provides an organic light emitting device including the compound represented by the above chemical formula 1. The organic light emitting device described above may include one or more organic layers containing the compound of the present invention between the first electrode and the second electrode.
In one embodiment of the present invention, the organic layer may be one or more of a hole injection layer, a hole transport layer and a light emitting auxiliary layer, for example, but may not be limited thereto, and in this case, the compound of the present invention may be used alone or in combination with a known organic light emitting compound.
In the present invention, the light-emitting auxiliary layer refers to a layer formed between the hole transport layer and the light-emitting layer, and may be referred to as a second hole transport layer, a third hole transport layer, or the like depending on the number of hole transport layers.
In one example of the present invention, the organic light emitting device may include an organic layer including a hole transporting substance and an organic layer including a compound represented by the above chemical formula 1, but may not be limited thereto.
The organic light emitting device may include one or more organic layers such as a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an emission layer (EML), an Electron Transport Layer (ETL), and an Electron Injection Layer (EIL) between an anode (anode) and a cathode (cathode).
For example, the above-described organic light emitting device may be manufactured according to the structure described in fig. 1. The organic light emitting device may sequentially stack an anode (hole injection electrode 1000)/hole injection layer 200/hole transport layer 300/light emitting layer 400/electron transport layer 500/electron injection layer 600/cathode (electron injection electrode 2000) from bottom to top.
In fig. 1, a substrate for an organic light emitting device may be used as the substrate 100, and in particular, a transparent glass substrate or a bendable plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water repellency may be used.
The hole injection electrode 1000 serves as an anode for injecting holes of the organic light emitting device. In order to inject holes, a material having a low work function may be formed of a transparent material such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), or graphene (graphene).
The hole injection layer 200 may be formed by depositing a hole injection layer material on the anode electrode by a vacuum deposition method, a spin coating method, a casting method, an LB (Langmuir-Blodgett) method, or the like. In the case of forming the hole injection layer by the above vacuum deposition method, the deposition conditions thereof are different depending on the compound used as the material of the hole injection layer, the structure and thermal characteristics of the hole injection layer desired, etc., but may be generally at a deposition temperature of 50-500 ℃, a vacuum degree of 10 -8 to 10 -3 torr, 0.01 toDeposition rate of (2),The layer thickness to 5 μm is suitably selected.
Next, a hole transporting layer substance is deposited on the hole injecting layer 200 by a vacuum deposition method, a spin coating method, a casting method, an LB method, or the like, whereby the hole transporting layer 300 can be formed. In the case of forming the hole transport layer by the above vacuum deposition method, the deposition conditions thereof are different depending on the compound used, but in general, it is preferable to select in the range of conditions almost the same as the formation of the hole injection layer. The hole transport layer may be one or more layers, for example, a first hole transport layer and a second hole transport layer (light-emitting auxiliary layer). At least one of the first hole transporting layer and the second hole transporting layer may include the compound of formula 1 of the present invention.
Next, a light-emitting layer substance is deposited over the hole-transporting layer or the light-emitting auxiliary layer by a vacuum deposition method, a spin coating method, a casting method, an LB method, or the like, whereby the light-emitting layer 400 can be formed. In the case of forming the light-emitting layer by the above vacuum deposition method, the deposition conditions thereof are different depending on the compound used, but in general, it is preferable to select in the range of conditions almost the same as the formation of the hole injection layer. The light-emitting layer material may use a known compound as a host or a dopant.
In addition, when the light-emitting layer is used together with a phosphorescent dopant, a hole-suppressing material (HBL) may be laminated by a vacuum deposition method or a spin coating method in order to prevent diffusion of triplet excitons or holes into the electron-transporting layer. The hole-inhibiting substance that can be used in this case is not particularly limited, but any substance can be selected from known substances used as hole-inhibiting materials and used. For example, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and hole-suppressing materials described in Japanese patent application laid-open No. 11-329734 (A1) are exemplified, and typically Balq (bis (8-hydroxy-2-methylquinoline) -aluminum biphenol), phenanthroline (phe nanthrolines) compounds (for example, BCP (Basso Coupoline) by general display (UDC)) and the like are used.
An electron transporting layer 500 is formed on the light emitting layer 400 formed as described above, and in this case, the electron transporting layer may be formed by a vacuum deposition method, a spin coating method, a casting method, or the like. The deposition conditions of the electron transport layer are different depending on the compound used, but in general, it is preferable to select the conditions within the range substantially equal to the conditions for forming the hole injection layer.
Thereafter, an electron injection layer material may be deposited on the electron transport layer 500 to form the electron injection layer 600, and in this case, the electron transport layer may be formed into a conventional electron injection layer material by a vacuum deposition method, a spin coating method, a casting method, or the like.
The hole injection layer 200, the hole transport layer 300, the light emitting layer 400, and the electron transport layer 500 of the above device may use the compound of the present invention or the following substances, or may use the compound of the present invention together with known substances.
The cathode 2000 for injecting electrons is formed on the electron injection layer 600 by a vacuum deposition method, a sputtering method, or the like. As the cathode, various metals can be used. Specific examples include aluminum, gold, silver, and the like.
The organic light-emitting device of the invention can not only adopt an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode structure, but also adopt the structures of organic light-emitting devices with various structures, and can also form one or two layers of intermediate layers according to requirements.
As described above, the thickness of each organic layer formed according to the present invention may be adjusted according to a desired degree, and preferably, it is specifically 10 to 1000nm, more specifically 20 to 150nm.
In the present invention, the organic layer containing the compound represented by chemical formula 1 has advantages in that the thickness of the organic layer can be adjusted to a molecular unit, and thus the surface is uniform and the morphological stability is excellent.
The organic light-emitting compound according to the first embodiment of the present invention is not limited to any particular one, and may be any one as long as it is a compound having a high molecular weight.
Hereinafter, the present invention will be described more specifically with reference to examples, but the scope of the present invention is not limited to the examples.
Examples
Preparation example 1 Synthesis of IM
For synthesizing the target compound, IM may be prepared by synthesizing the target compound by any one of the above steps, which may not be limited thereto.
The synthesis of IM1 is described below.
In a round-bottomed flask, after 27.6g of [1,1' -biphenyl ] -4-ylboronic acid and 50.0g of 4-bromo-4 ' -iodo-1, 1' -biphenyl were dissolved in 800ml of 1, 4-dioxane, K 2CO3 (2M) 210ml and Pd (PPh 3)4 4.8.8 g were put into reflux and stirred, the reaction was confirmed by Thin Layer Chromatography (TLC) and after water was added, the reaction was terminated, the organic layer was extracted by Methylcellulose (MC) and filtered under reduced pressure, and then recrystallized to obtain 50.4g (yield 74%) of intermediate IM1.
By the same method as in IM1 described above, the following IM2 to IM13 were synthesized using different starting materials.
PREPARATION EXAMPLE 2 Synthesis of OP
The following synthesis of OP1 is described below.
15.0G of the above-mentioned 2-bromo-9, 9-dimethyl-9H-fluorene, 5.6g of aniline, t-Buona 7.9g, pd 2(dba)3 2.0g、(t-Bu)3 P2.5 ml were dissolved in 200ml of toluene in a round-bottomed flask, and then stirred under reflux. After confirming the reaction by Thin Layer Chromatography (TLC) and adding water, the reaction was terminated. The organic layer was extracted with Methyl Cellulose (MC), and after filtration under reduced pressure, recrystallization was performed to obtain 11.75g (yield 75%) of OP1.
By the same method as the above OP1, the following OP2 to OP3 were synthesized using different starting materials.
Synthesis example 1 Synthesis of Compound 1
In a round-bottomed flask, 5.0g of IM 1, 3.7g of OP1, t-Buona 1.9g, pd 2(dba)3 0.5g、(t-Bu)3 P0.5 ml were dissolved in 130ml of toluene and stirred under reflux. After confirming the reaction by Thin Layer Chromatography (TLC) and adding water, the reaction was terminated. The organic layer was extracted with Methyl Cellulose (MC), and after filtration under reduced pressure, column purification and recrystallization were performed to obtain 5.36g (yield 70%) of compound 1.
m/z：589.28(100.0％)、590.28(49.1％)、591.28(11.8％)、592.29(1.8％)
Synthesis example 2 Synthesis of Compound 2
Compound 2 was synthesized by the same method as compound 1, using OP2 instead of OP 1. (yield 68%)
m/z：639.29(100.0％)、640.30(53.4％)、641.30(14.0％)、642.30(2.4％)
Synthesis example 3 Synthesis of Compound 3
Compound 3 was synthesized by the same method as compound 1, using OP3 instead of OP 1. (yield 65%)
m/z：713.31(100.0％)、714.31(60.3％)、715.31(17.6％)、716.32(3.4％)
Synthesis example 4 Synthesis of Compound 4
Compound 4 was synthesized by the same method as compound 1, using IM2 and OP3 instead of IM1 and OP 1. (yield 72%)
m/z：713.31(100.0％)、714.31(60.3％)、715.31(17.6％)、716.32(3.4％)
Synthesis example 5 Synthesis of Compound 5
Compound 5 was synthesized by the same method as compound 1, using IM3 and OP3 instead of IM1 and OP 1. (yield 65%)
m/z：713.31(100.0％)、714.31(60.3％)、715.31(17.6％)、716.32(3.4％)
Synthesis example 6 Synthesis of Compound 6
Compound 6 was synthesized by the same method as compound 1, using IM4 and OP3 instead of IM1 and OP 1. (yield 67%)
m/z：713.31(100.0％)、714.31(60.3％)、715.31(17.6％)、716.32(3.4％)
Synthesis example 7 Synthesis of Compound 7
Compound 7 was synthesized by the same method as compound 1 using IM5 and OP3 instead of IM1 and OP 1. (yield 62%)
m/z：713.31(100.0％)、714.31(60.3％)、715.31(17.6％)、716.32(3.4％)
Synthesis example 8 Synthesis of Compound 8
Compound 8 was synthesized by the same method as compound 1, using IM6 and OP3 instead of IM1 and OP 1. (yield 63%)
m/z：713.31(100.0％)、714.31(60.3％)、715.31(17.6％)、716.32(3.4％)
Synthesis example 9 Synthesis of Compound 9
Compound 9 was synthesized by the same method as compound 1 using IM7 and OP3 instead of IM1 and OP 1. (yield 63%)
m/z：713.31(100.0％)、714.31(60.3％)、715.31(17.6％)、716.32(3.4％)
Synthesis example 10 Synthesis of Compound 10
Compound 10 was synthesized by the same method as compound 1, using IM8 and OP3 instead of IM1 and OP 1. (yield 60%)
m/z：713.31(100.0％)、714.31(60.3％)、715.31(17.6％)、716.32(3.4％)
Synthesis example 11 Synthesis of Compound 11
Compound 11 was synthesized by the same method as compound 1, using IM9 and OP3 instead of IM1 and OP 1. (yield 56%)
m/z：713.31(100.0％)、714.31(60.3％)、715.31(17.6％)、716.32(3.4％)
Synthesis example 12 Synthesis of Compound 12
Compound 12 was synthesized by the same method as compound 1, using IM10 and OP3 instead of IM1 and OP 1. (yield 60%)
m/z：713.31(100.0％)、714.31(60.3％)、715.31(17.6％)、716.32(3.4％)
Synthesis example 13 Synthesis of Compound 13
Compound 13 was synthesized by the same method as compound 1, using IM11 and OP3 instead of IM1 and OP 1. (yield 58%)
m/z：713.31(100.0％)、714.31(60.3％)、715.31(17.6％)、716.32(3.4％)
Synthesis example 14 Synthesis of Compound 14
Compound 14 was synthesized by the same method as compound 1 using IM12 and OP3 instead of IM1 and OP 1. (yield 60%)
m/z：713.31(100.0％)、714.31(60.3％)、715.31(17.6％)、716.32(3.4％)
Synthesis example 15 Synthesis of Compound 15
Compound 15 was synthesized by the same method as compound 1, using IM13 and OP3 instead of IM1 and OP 1. (yield 48%)
m/z：713.31(100.0％)、714.31(60.3％)、715.31(17.6％)、716.32(3.4％)
Example 1: fabrication of organic light emitting devices
By ultrasonic pairing of distilled waterThe glass substrate coated with Indium Tin Oxide (ITO) into a thin film was washed. After the distilled water washing is completed, ultrasonic washing is performed by using solvents such as isopropanol, acetone and methanol, drying is performed, the substrate is transferred to a plasma cleaning machine, and is cleaned by using oxygen plasma for 5 minutes, and then a thermal vacuum deposition device (thermal evaporator) is used as a hole injection layer on the upper part of the indium tin oxide substrateH101 of (2) is subjected to film formationIs formed into a film as a hole transport layerIs formed into a film as a light-emitting auxiliary layerAfter the compound 1 of (a) was formed into a film, 3% BH01 was doped as the light-emitting layer: BD01 toAnd (5) film formation is carried out. Then, as an electron transport layerET01 of (c): liq (1:1) was subjected to film formation, and thenLiF (LiF),Film formation was performed on aluminum (Al) of (a) and the device was sealed (Encapsulation) in a glove box, thereby preparing an organic light emitting device.
Examples 2 to 15: preparation of organic light-emitting device
Using the same method as in example 1, an organic light-emitting device in which a light-emitting auxiliary layer was formed using compounds 2 to 15 instead of compound 1 was produced.
Comparative examples 1 to 9
An organic light-emitting device was prepared using the same method as in example 1, and using the following ref.1 to ref.9 instead of the compound 1, respectively.
Experimental example 1: performance evaluation of organic light emitting device
The performance of the organic light emitting devices of examples and comparative examples was evaluated by applying a voltage to inject electrons and holes using a source measurement unit (Kiethley 2400source measureme nt unit) of Ji-Li 2400, and measuring the luminance at the time of light emission using a Konica Minolta spectroradiometer (CS-2000), thereby measuring the current density and luminance for the applied voltage under the atmospheric pressure condition, and the results are shown in Table 1.
TABLE 1
| Op.V | mA/cm2 | Cd/A | QE(％) | CIEx | CIEy | LT97 | |
| Example 1 | 3.85 | 10 | 7.13 | 6.04 | 0.140 | 0.109 | 115 |
| Example 2 | 3.86 | 10 | 7.15 | 6.00 | 0.140 | 0.110 | 118 |
| Example 3 | 3.91 | 10 | 7.25 | 6.23 | 0.140 | 0.109 | 132 |
| Example 4 | 3.97 | 10 | 7.45 | 6.28 | 0.140 | 0.110 | 153 |
| Example 5 | 3.92 | 10 | 7.40 | 6.25 | 0.141 | 0.110 | 152 |
| Example 6 | 3.91 | 10 | 7.37 | 6.25 | 0.140 | 0.110 | 151 |
| Example 7 | 3.92 | 10 | 7.40 | 6.25 | 0.140 | 0.110 | 152 |
| Example 8 | 3.90 | 10 | 7.40 | 6.20 | 0.140 | 0.109 | 150 |
| Example 9 | 3.90 | 10 | 7.38 | 6.22 | 0.139 | 0.110 | 153 |
| Example 10 | 3.90 | 10 | 7.35 | 6.23 | 0.141 | 0.110 | 150 |
| Example 11 | 3.92 | 10 | 7.35 | 6.25 | 0.140 | 0.110 | 150 |
| Example 12 | 3.90 | 10 | 7.48 | 6.21 | 0.140 | 0.111 | 144 |
| Example 13 | 3.95 | 10 | 7.38 | 6.20 | 0.140 | 0.110 | 153 |
| Example 14 | 3.95 | 10 | 7.42 | 6.25 | 0.140 | 0.110 | 150 |
| Example 15 | 3.95 | 10 | 7.47 | 6.29 | 0.141 | 0.110 | 151 |
| Comparative example 1 | 4.25 | 10 | 6.40 | 5.68 | 0.142 | 0.111 | 70 |
| Comparative example 2 | 4.28 | 10 | 6.94 | 5.76 | 0.143 | 0.110 | 82 |
| Comparative example 3 | 4.05 | 10 | 6.48 | 5.44 | 0.141 | 0.112 | 70 |
| Comparative example 4 | 4.03 | 10 | 6.54 | 5.50 | 0.141 | 0.111 | 75 |
| Comparative example 5 | 4.02 | 10 | 6.90 | 5.35 | 0.141 | 0.110 | 89 |
| Comparative example 6 | 4.05 | 10 | 6.49 | 5.50 | 0.143 | 0.110 | 62 |
| Comparative example 7 | 4.09 | 10 | 6.51 | 5.71 | 0.141 | 0.111 | 67 |
| Comparative example 8 | 4.05 | 10 | 6.88 | 5.60 | 0.141 | 0.110 | 85 |
| Comparative example 9 | 4.09 | 10 | 7.02 | 5.60 | 0.141 | 0.111 | 97 |
As shown in table 1, the results of the driving voltage reduction, efficiency and life increase were seen in the examples of the present invention compared with comparative examples 1 to 9.
More specifically, in the examples of the present invention, 1) hole mobility can be increased by conjugate expansion by linear linkage of 4 phenyl groups as compared with comparative examples 1 to 3, 2) the other side of aryl group other than the aryl group of arylamine as compared with comparative examples 4 and 5 is minimized to aryl group of C 10 or less, appropriate HOMO, LUMO and high T1 can be maintained, 3) molecular arrangement on a thin film becomes excellent by the aryl group linearly linked as compared with comparative examples 6 to 8, hole mobility can be faster, 4) high purity purification can be easily achieved without substituting for heavy hydrogen as compared with comparative example 9, and long life of an organic light emitting device can be induced.
The above description of the present invention is for illustrative purposes, and those skilled in the art to which the present invention pertains will appreciate that it can be easily modified in other specific ways without changing the technical idea or essential features of the present invention. Accordingly, it should be understood that the various embodiments described above are illustrative in all respects, rather than restrictive. For example, each constituent element described as a single type may be implemented in a distributed manner, and a plurality of constituent elements described as distributed may be implemented in a combined manner.
The scope of the invention is indicated by the appended claims rather than by the foregoing detailed description, and all changes and modifications that come within the meaning and range of equivalency of the claims and are therefore intended to be embraced therein.
Claims (5)
1. A compound represented by the following chemical formula 4:
Chemical formula 4
In the chemical formula 4 described above, the chemical formula,
R 1 to R 3 are each hydrogen,
L is 0 or an integer from 1 to 4, m is 0 or an integer from 1 to 3,
N is 0 or an integer from 1 to 5,
R 4 and R 5 are each independently hydrogen,
R 6 to R 8 are each independently hydrogen;
r 9 is hydrogen, and the hydrogen atom,
In the chemical formula 4, the chemical formula is represented byThe substituents represented have more than one meta or ortho bond.
2. The compound according to claim 1, wherein the compound represented by the chemical formula 4 is one of the following compounds:
3. An organic light-emitting device comprising an organic layer comprising the compound of claim 1 between a first electrode and a second electrode.
4. The organic light-emitting device according to claim 3, wherein the organic layer is 1 or more layers of a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer.
5. The organic light-emitting device according to claim 4, wherein the organic layer is a light-emitting auxiliary layer.
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| KR10-2017-0086672 | 2017-07-07 | ||
| KR1020170086672A KR102559469B1 (en) | 2017-07-07 | 2017-07-07 | Novel compound and organic electroluminescent divice including the same |
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