CN111936481A - 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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- CN111936481A CN111936481A CN201980023698.XA CN201980023698A CN111936481A CN 111936481 A CN111936481 A CN 111936481A CN 201980023698 A CN201980023698 A CN 201980023698A CN 111936481 A CN111936481 A CN 111936481A
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- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
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- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003943 azolyl group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- JUMBNTOZUIMCEL-UHFFFAOYSA-N n-(4-phenylphenyl)naphthalen-2-amine Chemical compound C=1C=C2C=CC=CC2=CC=1NC(C=C1)=CC=C1C1=CC=CC=C1 JUMBNTOZUIMCEL-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Abstract
The present invention relates to a novel compound and an organic light emitting device including the same, and the novel compound according to an embodiment of the present invention is suitable for an organic light emitting device and can ensure high efficiency, long life, low driving voltage, and driving stability of the organic light emitting device.
Description
Technical Field
The present invention relates to a novel compound and an organic light emitting device 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 light-emitting materials may be classified into high-molecular and low-molecular materials according to molecular weight, fluorescent materials in a singlet excited state derived from electrons and phosphorescent materials in a triplet excited state derived from electrons according to a light-emitting mechanism, and blue, green and red light-emitting materials and yellow and orange light-emitting materials required for embodying a better natural color may be classified according to light emission 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 small amount of a dopant having a smaller energy band gap and excellent light emission efficiency than a host mainly constituting a light emitting layer is mixed in an auxiliary layer, excitons generated in the host are transported to the dopant, and light with high efficiency is emitted. In this case, since the wavelength of the host is shifted to the wavelength band of the dopant, light having a desired wavelength can be obtained according to the type of the dopant and the host used.
Many compounds have been known as materials used in such organic light emitting devices, but in the case of organic light emitting devices using the materials known so far, development of new materials is continuously required due to high driving voltage, low efficiency and short lifetime. Accordingly, efforts are continuously made to develop an organic light emitting device having low voltage driving, high luminance, and long life using a substance having excellent characteristics.
Disclosure of Invention
Technical problem
The present invention provides a novel organic compound and an organic light emitting device including 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 may be clearly understood by those skilled in the art from the following description.
Technical scheme
A first embodiment of the present invention provides a compound represented by the following chemical formula 1:
chemical formula 1
In the above-described chemical formula 1,
x is O, S or CRR',
Ar1is substituted or unsubstituted C6～C50Aryl of (2), or substituted or unsubstituted C5～C50The heteroaryl group of (a) is a group,
Ar2is substituted or unsubstituted C12～C50The aryl group of (a) is,
R、R`、R1to R6Each independently hydrogen, halogen, nitro, nitrile, substituted or unsubstituted C1～C30Alkyl, substituted or unsubstituted C2～C30Alkenyl of (a), substituted or unsubstituted C1～C30Alkoxy, substituted or unsubstituted C1～C30Sulfide group, substituted or unsubstituted C6～C30Aryl of (2), or substituted or unsubstituted C5～C30Heteroaryl of (a), adjacent multiple R1Between, a plurality of R2Between, a plurality of R3Or R and R' may be bonded to each other to form a ring or not, R4And R6Or R5And R6Can be combined to form a ring or not form a ring,
L1is a direct bond, substituted or unsubstituted C6～C30Or substituted or unsubstituted C5～C30The heteroarylene group of (a) is,
L2is substituted or unsubstituted C6～C30Or substituted or unsubstituted C5～C30The heteroarylene group of (a) is,
l is 0 or an integer of 1 to 4, m and n are each independently 0 or an integer of 1 to 3, and when the above-mentioned l, m or n is 2 or more, R1、R2And R3Can each be the same or different.
A second embodiment of the present invention provides an organic light-emitting device including an organic layer containing the compound of the present invention between a first electrode and a second electrode.
ADVANTAGEOUS EFFECTS OF INVENTION
In the compound according to an example of the present invention, a tricyclic fused ring group (dibenzofuran, dibenzothiophene, or fluorene) and dibenzofuran are linked to nitrogen of arylamine through a linking group, whereby a HOMO level suitable for an emission auxiliary layer can be formed, whereby a high-efficiency organic light-emitting device can be realized.
In addition, the compound according to an embodiment of the present invention has a tricyclic fused ring group with excellent electron tolerance introduced on the arylamine side, maintains high LUMO and T1, easily blocks electrons, and maximizes the exciton confinement effect in the light-emitting layer. Thus, an organic light emitting device having high efficiency and long life can be realized.
In addition, the compound according to an embodiment of the present invention uses the 2 nd or 4 th position of dibenzofuran having a small bulk property as a connecting position on the arylamine side, and thus can provide an organic light emitting device having a long lifetime by realizing a low voltage and suppressing a roll-off phenomenon, while making the arrangement of molecules excellent when a thin film is formed.
Also, in the compound of an embodiment of the present invention, one side of arylamine is connected to dibenzofuran through a linker and the other side has an aryl group, thereby increasing pi-conjugation. Thereby improving Hole mobility (Hole mobility) and realizing low driving voltage when being applied to an organic light emitting device.
Further, according to the compound of one embodiment of the present invention, a tricyclic fused ring group expanded by dibenzofuran is included on one side of arylamine to form a high Tg, so that recrystallization of a thin film can be prevented, thereby ensuring driving stability of an organic light emitting device.
Drawings
Fig. 1 shows a schematic view of an organic light emitting device according to an embodiment of the present invention.
Detailed Description
Examples and embodiments of the present invention are described in detail below with reference to the accompanying drawings so that those skilled in the art can easily implement the invention.
However, the present invention can be realized in various forms and is not limited to the examples and embodiments described herein. In the drawings, for the purpose of clearly explaining the present invention, portions not related to the explanation are omitted, and like reference numerals are given to like portions throughout the specification.
Throughout the present specification, when an element is "on" another element, it includes not only the case where the element is in contact with the other element, but also the case where the other element is present between the two elements.
Throughout the present specification, when a portion "includes" a structural element, it is meant that other structural elements may be included, but not excluded, unless otherwise stated. The terms "about," "substantially," and the like, as used throughout the specification are used in the sense of their numbers or close to their numbers to indicate inherent preparation and material tolerances, so as to prevent an assiduous intruder from inadvertently making use of the disclosure in which exact or absolute numbers are mentioned to assist in understanding the invention. The term "step(s)" or "step(s)" used throughout the present specification does not mean "step(s) used for.
Throughout the present specification, the term "combination thereof" contained in an expression of Markush (Markush) means a mixture or combination of one or more kinds selected from the group consisting of a plurality of structural elements described in an expression of Markush, and means including one or more kinds selected from the group consisting of the plurality of structural elements.
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" is meant to encompass C6-50The aromatic hydrocarbon ring group of (2), for example, phenyl, benzyl, naphthyl, biphenyl, terphenyl, fluorene, phenanthryl, triphenylalkenyl, phenylalkenyl,
Fluoranthenyl, benzofluorenyl, benzotrichenyl, benzotriphenylenyl, benzo
An aromatic ring such as a phenyl group, an anthracenyl group, a stilbene group, or a pyrenyl group, and a "heteroaryl group" is a group containing at least one hetero element C5-50Aromatic rings of (2), e.g.Such as, meant to include pyrrolinyl, pyrazinyl, pyridyl, indolyl, isoindolyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, benzothienyl, dibenzothienyl, quinolyl, isoquinolyl, quinoxalyl, carbazolyl, phenanthryl cry, acridinyl, phenanthrolinyl, thienyl, and substituted by a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a triazine ring, an indole ring, a quinoline ring, an acridine ring, a pyrrolidine ring, a bisdiazepine ring
An alkyl ring, a piperidine ring, a morpholine ring, a piperazine ring, a carbazole ring, a furan ring, a thiophene ring,
An azolyl ring,
Diazole ring, benzo
A heterocyclic group formed by an azole ring, a thiazole ring, a thiadiazole ring, a benzothiazole ring, a triazole ring, an imidazole ring, a benzimidazole ring, a pyran ring, a dibenzofuran ring or a dibenzothiophene ring.
Throughout the present specification, the term "substituted or unsubstituted" may be meant to be selected from the group consisting of halogen, amino, nitrile, nitro or C1～C20Alkyl of (C)2～C20Alkenyl of, C1～C20Alkoxy group of (C)3～C20Cycloalkyl of, C3～C20Heterocycloalkyl of (A), C6～C30Aryl and C3～C30One or more groups of the group consisting of heteroaryl groups of (a) are substituted or unsubstituted. In addition, throughout the present specification, the same reference numerals may have the same meaning unless otherwise specified.
Throughout the description of the present invention, the term "fluorene" may comprise a C substituted or unsubstituted hydrogen bonded to the carbon at position 91-20Alkyl, substitutedOr unsubstituted C5-30Aryl of (2), or substituted or unsubstituted C3-30And (3) heteroaryl substituted.
A first embodiment of the present invention provides a compound represented by the following chemical formula 1.
Chemical formula 1
In the above-described chemical formula 1,
x is O, S or CRR',
Ar1is substituted or unsubstituted C6～C50Aryl of (2), or substituted or unsubstituted C5～C50The heteroaryl group of (a) is a group,
Ar2is substituted or unsubstituted C12～C50The aryl group of (a) is,
R、R`、R1to R6Each independently hydrogen, halogen, nitro, nitrile, substituted or unsubstituted C1～C30Alkyl, substituted or unsubstituted C2～C30Alkenyl of (a), substituted or unsubstituted C1～C30Alkoxy, substituted or unsubstituted C1～C30Sulfide group, substituted or unsubstituted C6～C30Aryl of (2), or substituted or unsubstituted C5～C30Heteroaryl of (a), adjacent multiple R1Between, a plurality of R2Between, a plurality of R3Or R and R' may be bonded to each other to form a ring or not, R4And R6Or R5And R6Can be combined to form a ring or not form a ring,
L1is a direct bond, substituted or unsubstituted C6～C30Or substituted or unsubstituted C5～C30The heteroarylene group of (a) is,
L2is substituted or unsubstituted C6～C30Or substituted or unsubstituted C5～C30The heteroarylene group of (a) is,
l is 0 or an integer from 1 to 4,
m and n are each independently 0 or an integer of 1 to 3, and when the above-mentioned l, m or n is 2 or more, R1、R2And R3Can each be the same or different.
In the compound according to an example of the present invention, a tricyclic fused ring group (dibenzofuran, dibenzothiophene, or fluorene) and dibenzofuran are linked to nitrogen of arylamine through a linking group, whereby a HOMO level suitable for an emission auxiliary layer can be formed, whereby a high-efficiency organic light-emitting device can be realized.
In addition, the compound according to an embodiment of the present invention has a tricyclic fused ring group with excellent electron tolerance introduced on the arylamine side, maintains high LUMO and T1, easily blocks electrons, and maximizes the exciton confinement effect in the light-emitting layer. Thus, an organic light emitting device having high efficiency and long life can be realized.
In addition, the compound according to an embodiment of the present invention uses the 2 nd or 4 th position of dibenzofuran having a small bulk property as a connecting position on the arylamine side, and thus can provide an organic light emitting device having a long lifetime by realizing a low voltage and suppressing a roll-off phenomenon, while making the arrangement of molecules excellent when a thin film is formed.
The number of the linking position of the tricyclic fused ring compound is as follows.
Also, in the compound of an embodiment of the present invention, one side of arylamine is connected to dibenzofuran through a linker and the other side has an aryl group, thereby increasing pi-conjugation. Thereby improving Hole mobility (Hole mobility) and realizing low driving voltage when being applied to an organic light emitting device.
Further, according to the compound of one embodiment of the present invention, a tricyclic fused ring group expanded by dibenzofuran is included on one side of arylamine to form a high Tg, so that recrystallization of a thin film can be prevented, thereby ensuring driving stability of an organic light emitting device.
In one embodiment of the present invention, the above compound may be represented by the following chemical formula 2.
Chemical formula 2
In the above-described chemical formula 2,
X、Ar1、Ar2、R、R`、R1to R6、L1L, m and n are as defined in the above chemical formula 1,
R7is hydrogen, halogen, nitro, nitrile, substituted or unsubstituted C1～C30Alkyl, substituted or unsubstituted C2～C30Alkenyl of (a), substituted or unsubstituted C1～C30Alkoxy, substituted or unsubstituted C1～C30Sulfide group, substituted or unsubstituted C6～C30Aryl of (2), or substituted or unsubstituted C5～C30The heteroaryl group of (a) is a group,
o is an integer of 1 to 4, p is 0 or an integer of 1 to 4, and when the above o or p is 2 or more, R is7Can be the same or different, and when o is 2 or more, p can be the same or different.
The compound represented by the above chemical formula 2 is L in the above chemical formula 12When the compound contains a phenylene group, one or more phenylene groups as a linking group are bonded to the substituent dibenzofuran of the arylamine and the nitrogen of the arylamine. In this case, the compound can maintain high T1 due to the phenylene group while forming HOMO suitable for the light emission assisting layer, and thus the exciton can be blocked more effectively.
In one embodiment of the present invention, the above compound may be represented by the following chemical formula 3.
Chemical formula 3
In the above-mentioned chemical formula 3,
X、Ar1、Ar2、R、R`、R1to R6L, m and n are as defined in the above chemical formula 1,
R7is hydrogen, halogen, nitro, nitrile, substituted or unsubstituted C1～C30Alkyl, substituted or unsubstituted C2～C30Alkenyl of (a), substituted or unsubstituted C1～C30Alkoxy, substituted or unsubstituted C1～C30Sulfide group, substituted or unsubstituted C6～C30Aryl of (2), or substituted or unsubstituted C5～C30The heteroaryl group of (a) is a group,
o is an integer from 1 to 4, p is 0 or an integer from 1 to 4,
when o or p is 2 or more, R7Can be the same or different, and when o is 2 or more, p can be the same or different.
The compound represented by the above chemical formula 3 is L in the above chemical formula 11In the case of direct bonding, dibenzofuran is directly bonded to a tricyclic fused ring group (dibenzofuran, dibenzothiophene, or fluorene) to form a deep HOMO level, whereby a high-efficiency organic light-emitting device can be realized.
In one embodiment of the present invention, the above compound may be represented by the following chemical formula 4 or chemical formula 5.
Chemical formula 4
Chemical formula 5
In the above chemical formulas 4 and 5,
Ar1、Ar2、R1to R6L and n are as defined in the above chemical formula 1,
x is O or S, and X is O or S,
R2can be the same or different and can be,
R7is hydrogen, halogen, nitro, nitrile, substituted or unsubstituted C1～C30Alkyl, substituted or unsubstituted C2～C30Alkenyl of (a), substituted or unsubstituted C1～C30Alkoxy, substituted or unsubstituted C1～C30Sulfide group, substituted or unsubstituted C6～C30Aryl of (2), or substituted or unsubstituted C5～C30The heteroaryl group of (a) is a group,
o is an integer from 1 to 4, p is 0 or an integer from 1 to 4,
when o or p is 2 or more, R7Can be the same or different, and when o is 2 or more, p can be the same or different.
In this case, since the high LUMO is maintained while maintaining the fast hole mobility, the low voltage driving is effectively realized, and the inflow of electrons from the light emitting layer to the hole transporting layer can be effectively blocked.
In one embodiment of the present invention, the above compound may be represented by the following chemical formula 6.
Chemical formula 6
In the chemical formula 6 described above,
Ar1、Ar2、R、R'、R1to R6L, m and n are as defined in the above chemical formula 1,
R7is hydrogen, halogen, nitro, nitrile, substituted or unsubstituted C1～C30Alkyl, substituted or unsubstituted C2～C30Alkenyl of (a), substituted or unsubstituted C1～C30Alkoxy, substituted or unsubstituted C1～C30Sulfide group, substituted or unsubstituted C6～C30Aryl of (2), or substituted or unsubstituted C5～C30The heteroaryl group of (a) is a group,
o is an integer from 1 to 4, p is 0 or an integer from 1 to 4,
when o or p is 2 or more, R7Can be the same or different, and when o is 2 or more, p can be the same or different.
In this case, the fluorene maintains a fast hole mobility and a high Tg, thereby contributing to low voltage driving and improvement of driving stability.
In one example of the present invention, the above compound may be represented by the following chemical formula 7 or chemical formula 8.
Chemical formula 7
Chemical formula 8
In the above chemical formulas 7 and 8,
Ar1、Ar2、R1to R6L and n are as defined in the above chemical formula 1,
x is O or S, and X is O or S,
R2can be the same or different and can be,
R7is hydrogen, halogen, nitro, nitrile, substituted or unsubstituted C1～C30Alkyl, substituted or unsubstituted C2～C30Alkenyl of (a), substituted or unsubstituted C1～C30Alkoxy, substituted or unsubstituted C1～C30Sulfide group, substituted or unsubstituted C6～C30Aryl of (2), or substituted or unsubstituted C5～C30The heteroaryl group of (a) is a group,
o is an integer from 1 to 4, p is 0 or an integer from 1 to 4,
when o or p is 2 or more, R7Can be the same or different, when o is 2 or more,p can be the same or different.
In this case, the LUMO and T1 can be high while having a fast hole mobility, thereby easily blocking electrons and excitons, and effectively improving the light emitting efficiency and lifetime by improving the roll-off phenomenon.
According to an embodiment of the present invention, in the above chemical formulas 1 to 8, l, m, n, o, and p may be 0. Also, according to an embodiment of the present invention, in the above chemical formulas 1 to 8, R1To R7Can be each independently hydrogen, C1～C10Alkyl groups of (a), or phenyl groups. More specifically, R1To R7And may be hydrogen or phenyl.
Also, according to an embodiment of the present invention, in the above chemical formulas 1 to 3 and 6, R and R' may be each independently C1～C3Alkyl group of (1).
Also, according to an embodiment of the present invention, in the above chemical formulas 1 to 5, 7 and 8, X may be O.
Also, according to an embodiment of the present invention, in the above chemical formulas 1 to 5, 7 and 8, X may be S.
According to an embodiment of the present invention, in the above chemical formulas 1 to 8, Ar1Selected from the group consisting of phenyl, naphthyl, biphenyl, terphenyl, fluorenyl, dialkylfluorenyl, diarylfluorenyl, dibenzofuranyl, dibenzothienyl, and combinations thereof, Ar2May be selected from the group consisting of biphenyl, phenylnaphthyl, terphenyl, fluorenyl, dialkylfluorenyl, diarylfluorenyl, dibenzofuranyl, dibenzothienyl, and combinations thereof.
Also, according to an embodiment of the present invention, in the above chemical formula 1, L2May be a substituted or unsubstituted C containing at least one 1, 4-phenylene or 1, 3-phenylene group6～C24An arylene group of (a).
According to an embodiment of the present invention, in the chemical formula 1, Ar is1、Ar2And L2May comprise a compound having a meta positionA bonded phenylene group.
Also, according to an embodiment of the present invention, in the chemical formula 1, Ar is described above1May be a biphenyl group having a meta bond or a terphenyl group having a meta bond, or Ar described above2It may be a biphenyl group having a meta linkage or a terphenyl group having a meta linkage.
Also, according to an example of the present invention, in the above chemical formula 1, one or more of the following a) to c) may be satisfied:
a)Ar1and Ar2Is biphenyl;
b)Ar1and Ar2At least one of which is C consisting of a six-membered ring14The above aryl group; and
c)L2is C10The arylene group above.
According to an embodiment of the present invention, in the chemical formulas 1 to 8, Ar is described above1Ar is selected from the group consisting of phenyl, biphenyl, terphenyl, dimethylfluorenyl, and combinations thereof2May be selected from the group consisting of biphenyl, terphenyl, dimethylfluorenyl, and combinations thereof.
According to an embodiment of the present invention, the compound represented by the above chemical formula 1 may be one of the following compounds, but is not limited thereto:
a 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 an embodiment of the present invention, the organic layer may be a hole injection layer, a hole transport layer, and a light emission auxiliary layer, but is not limited thereto. Further, when forming an organic layer, the compound of the present invention can be used alone or together with a known compound.
For an embodiment of the present invention, the organic light emitting device may include an organic layer containing a hole transport material and an organic layer including the compound represented by the above chemical formula 1, but is not 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 organic light emitting device may be prepared according to the structure described in fig. 1. The organic light emitting device may be sequentially stacked with an anode (hole injection electrode 1000)/a hole injection layer 200/a hole transport layer 300/a light emitting layer 400/an electron transport layer 500/an electron injection layer 600/a cathode (electron injection electrode 2000) from the bottom up.
In fig. 1, a substrate used 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 having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance 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 used, and the material 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-described vacuum deposition method, the deposition conditions thereof vary depending on the compound used as the material of the hole injection layer 200, the structure and thermal characteristics of the hole injection layer, and the like, but may be generally at a deposition temperature of 50 to 500 ℃, 10 ℃ or the like-8To 10-3Vacuum degree of torr, 0.01 to
The deposition rate of,
The layer thickness range to 5 μm is suitably selected.
Next, a hole transport layer material is deposited on the hole injection layer 200 by a vacuum deposition method, a spin coating method, a casting method, an LB method, or the like, thereby forming a hole transport layer 300. In the case of forming the hole transport layer by the above-described vacuum deposition method, the deposition conditions thereof vary depending on the compound used, but in general, it is preferable to select the conditions within the range substantially the same as the conditions for forming the hole injection layer.
The compound of the present invention can be used for the hole transport layer 300, and as described above, the compound of the present invention can be used alone or together with a known compound. In addition, according to an embodiment of the present invention, the hole transport layer 300 may be one or more layers, and may include a hole transport layer formed only of a known material. Also, according to an embodiment of the present invention, a light-emission auxiliary layer may be formed on the hole transport layer 300.
The light-emitting layer 400 can be formed by depositing a light-emitting material on the hole transport layer 300 or the light-emitting auxiliary layer by a vacuum deposition method, a spin coating method, a casting method, an LB method, or the like. In the case of forming the light-emitting layer by the above-described vacuum deposition method, the deposition conditions thereof differ depending on the compound used, but in general, it is preferable to select the conditions within the range substantially the same as the conditions for forming the hole injection layer. In addition, 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-inhibiting material (HBL) may be further 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, can be mentioned
Examples of the oxadiazole derivative, the triazole derivative, the phenanthroline derivative, and the hole-inhibiting material described in jp 11-329734 a1 a include Balq (bis (8-hydroxy-2-methylquinoline) -aluminum biphenoxide) and phenanthroline (phenanthrolines) compounds (e.g., BCP (bathocuproine, bathocuproine) available from Universal Display (UDC)).
The electron transport layer 500 is formed on the light emitting layer 400 formed as described above, and in this case, the electron transport layer may be formed by a method such as a vacuum deposition method, a spin coating method, or a casting method. The deposition conditions of the electron transport layer vary depending on the compound used, but in general, it is preferable to select the conditions within the range substantially the same as 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 at this time, the electron transport layer may be formed of a conventional electron injection layer material by a vacuum deposition method, a spin coating method, a casting method, or the like.
The compound of the present invention or the following substances may be used for the hole injection layer 200, the hole transport layer 300, the light-emitting layer 400, and the electron transport layer 500 of the organic light-emitting device, or the compound of the present invention and known substances may be used together.
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 thereof include aluminum, gold, and silver.
The organic light-emitting device of the invention can adopt not only an anode, a hole injection layer, a hole transport layer, a luminescent layer, an electron transport layer, an electron injection layer and an organic light-emitting device with a cathode structure, but also structures of organic light-emitting devices with various structures, and can also form a middle layer of one layer or two 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, specifically, 1 to 1000nm, more specifically, 5 to 200 nm.
In the present invention, the organic layer including the compound represented by chemical formula 1 has an advantage in that the surface is uniform and the morphological stability is excellent because the thickness of the organic layer can be adjusted to a molecular unit.
The organic compound of the present embodiment can be applied to the content described in the first embodiment of the present invention, but is not limited thereto.
Hereinafter, the present invention will be described more specifically with reference to examples, but the scope of the present invention is not limited to these examples.
[ examples ]
Synthesis of Compound represented by chemical formula 1
The compound represented by chemical formula 1 may be synthesized by the following reaction, without being limited thereto.
Synthesis of intermediate IM
For the synthesis of the target compound, the intermediate IM can be synthesized by, but not limited to, the following reaction.
Synthesis of intermediate IM1
Intermediate IM1 was synthesized as follows.
In a round-bottomed flask, 20.0g of dibenzo [ b, d ] was charged]Furan-4-ylboronic acid (dibenzo [ b, d ]]furan-4-ylboronic acid), 35.5g of 4,6-dibromodibenzo [ b, d ]]Thiophene (4, 6-dibromoibenzo [ b, d ]]thiophene) was dissolved in 900ml of 1, 4-bis
After the addition of the alkane (1,4-dioxan), 140ml of K were added2CO3(2M) and 3.3g of Pd (PPh)3)4Then, reflux stirring was carried out. The reaction was confirmed by Thin Layer Chromatography (TLC), and after water was added, the reaction was terminated. Using methylene chloride (MC), and then filtered under reduced pressure and recrystallized to obtain intermediate IM1-1(25.1g, yield 62%).
In a round-bottomed flask, 25.0g of the above IM1-1, 20g of bis (pinacolato) diboron were dissolved in 450ml of 1, 4-bis
After the alkane (1,4-dioxan), 17.2g of KOAc and 0.2g of Pd (dppf) Cl were placed2Then, reflux stirring was carried out. The reaction was confirmed by Thin Layer Chromatography (TLC), and after water was added, the reaction was terminated. The organic layer was extracted with dichloromethane (MC), filtered under reduced pressure, and then recrystallized to obtain intermediate IM1-2(20.8g, yield 75%).
In a round-bottomed flask, 22.0g of the above IM1-2, 14.9g of 1-bromo-4-iodobenzene (1-bromo-4-iodobenzene) were dissolved in 550ml of 1, 4-bis
After the addition of an alkane (1,4-dioxan), 63ml of K were added2CO3(2M) and 1.5g of Pd (PPh)3)4Then, reflux stirring was carried out. The reaction was confirmed by Thin Layer Chromatography (TLC), and after water was added, the reaction was terminated. The organic layer was extracted with dichloromethane (MC), filtered under reduced pressure, and then recrystallized to obtain intermediate IM1(14.0g, yield 60%).
Synthesis of intermediates IM2 to IM11
IM2 to IM11 were synthesized in the same manner as the above-mentioned IM1, except that the starting materials were changed as shown in Table 1 below.
[ Table 1]
Examples 1 to 20: synthesis of Compounds
Using the above intermediates IM1 to IM11, target compounds 1 to 20 were synthesized as follows.
Example 1: synthesis of Compound 1
In a round-bottomed flask, 3.0g of IM1, 2.17g of bis ([1,1' -biphenyl)]-4-yl) amine (di ([1,1' -biphenyl)]-4-yl) amine), 0.9g of t-BuONa, 0.2g of Pd2(dba)30.3ml of (t-Bu)3After dissolving P in 80ml of toluene, the mixture was stirred under reflux. The reaction was confirmed by thin layer chromatography, and after water was added, the reaction was terminated. The organic layer was extracted with dichloromethane, and subjected to filtration under reduced pressure, followed by column purification and recrystallization to obtain 3.0g of compound 1 (yield 67%).
m/z：729.27(100.0％)、730.27(58.9％)、731.27(17.4％)、732.28(3.2％)
Example 2: synthesis of Compound 2
Compound 2 was synthesized in the same manner as compound 1 using N- ([1,1' -biphenyl ] -4-yl) naphthalen-1-amine (N- ([1,1' -biphenyl ] -4-yl) naphthalen-1-amine) instead of di ([1,1' -biphenyl ] -4-yl) amine (yield 63%).
m/z：703.25(100.0％)、704.25(56.6％)、705.26(16.2％)、706.26(3.1％)
Example 3: synthesis of Compound 3
Compound 3 was synthesized in the same manner as compound 1 using N- ([1,1'-biphenyl ] -4-yl) naphthalen-2-amine instead of di ([1,1' -biphenyl ] -4-yl) amine (yield 65%).
m/z：703.25(100.0％)、704.25(56.6％)、705.26(16.2％)、706.26(3.1％)
Example 4: synthesis of Compound 4
Compound 4 was synthesized in the same manner as compound 1 using N- ([1,1' -biphenyl ] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine (N- ([1,1' -biphenyl ] -4-yl) -9, 9-dimethyl-9H-fluoro-2-amine) instead of di ([1,1' -biphenyl ] -4-yl) amine (yield 66%).
m/z：769.30(100.0％)、770.30(62.5％)、771.30(19.3％)、772.31(4.1％)
Example 5: synthesis of Compound 5
Compound 5 was synthesized in the same manner as compound 1 using N- ([1,1'-biphenyl ] -4-yl) -9, 9-dimethyl-9H-fluoren-3-amine instead of bis ([1,1' -biphenyl ] -4-yl) amine (yield 65%).
m/z：769.30(100.0％)、770.30(62.5％)、771.30(19.3％)、772.31(4.1％)
Example 6: synthesis of Compound 6
Compound 6 was synthesized in the same manner as compound 1 using N- ([1,1'-biphenyl ] -4-yl) -9, 9-dimethyl-9H-fluoren-4-amine instead of bis ([1,1' -biphenyl ] -4-yl) amine (yield 62%).
m/z：769.30(100.0％)、770.30(62.5％)、771.30(19.3％)、772.31(4.1％)
Example 7: synthesis of Compound 7
Compound 7 was synthesized in the same manner as compound 1 using IM10 instead of IM1 (yield 67%).
m/z：805.30(100.0％)、806.30(65.8％)、807.30(21.4％)、808.31(4.7％)
Example 8: synthesis of Compound 8
Compound 8 was synthesized in the same manner as compound 1 using IM2 instead of IM1 (yield 69%).
m/z：729.27(100.0％)、730.27(58.9％)、731.27(17.4％)、732.28(3.2％)
Example 9: synthesis of Compound 9
Compound 9 was synthesized in the same manner as compound 1 using IM3 instead of IM1 (yield 68%).
m/z：729.27(100.0％)、730.27(58.9％)、731.27(17.4％)、732.28(3.2％)
Example 10: synthesis of Compound 10
Compound 10 was synthesized in the same manner as compound 1 using IM4 instead of IM1 (yield 65%).
m/z：729.27(100.0％)、730.27(58.9％)、731.27(17.4％)、732.28(3.2％)
Example 11: synthesis of Compound 11
Compound 11 was synthesized in the same manner as compound 1 using IM5 instead of IM1 (yield 62%).
m/z：745.24(100.0％)、746.25(58.8％)、747.25(17.7％)、747.24(4.7％),748.25(3.5％)、748.24(2.7％)、746.24(1.2％)
Example 12: synthesis of Compound 12
Compound 12 was synthesized in the same manner as compound 1 using IM6 instead of IM1 (yield 65%).
m/z：745.24(100.0％)、746.25(58.8％)、747.25(17.7％)、747.24(4.7％)、748.25(3.5％)、748.24(2.7％)、746.24(1.2％)
Example 13: synthesis of Compound 13
Compound 13 was synthesized in the same manner as compound 1 using IM7 instead of IM1 (yield 62%).
m/z：745.24(100.0％)、746.25(58.8％)、747.25(17.7％)、747.24(4.7％)、748.25(3.5％)、748.24(2.7％)、746.24(1.2％)
Example 14: synthesis of Compound 14
Compound 14 was synthesized in the same manner as compound 1 using IM8 instead of IM1 (yield 65%).
m/z：745.24(100.0％)、746.25(58.8％)、747.25(17.7％)、747.24(4.7％)、748.25(3.5％)、748.24(2.7％)、746.24(1.2％)
Example 15: synthesis of Compound 15
Compound 15 was synthesized in the same manner as compound 1 using IM9 instead of IM1 (yield 60%).
m/z：755.32(100.0％)、756.32(62.1％)、757.33(19.0％)、758.33(3.9％)
Example 16: synthesis of Compound 16
Compound 16 was synthesized in the same manner as compound 1 using IM11 instead of IM1 (yield 65%).
m/z：805.30(100.0％)、806.30(65.8％)、807.30(21.4％)、808.31(4.7％)
Example 17: synthesis of Compound 17
Compound 17 was synthesized in the same manner as Compound 1, using N-phenyl- [1,1':4', 1' -terphenyl ] -4-amine (N-phenyl- [1,1':4', 1' -terphenyl ] -4-amine) in place of di ([1,1' -biphenyl ] -4-yl) amine (yield 65%).
m/z：729.27(100.0％)、730.27(58.9％)、731.27(17.4％)、732.28(3.2％)
Example 18: synthesis of Compound 18
Compound 18 was synthesized in the same manner as Compound 1, using N- ([1,1' -biphenyl ] -4-yl) - [1,1':3',1 "-terphenyl ] -4-amine (N- ([1,1' -biphenyl ] -4-yl) - [1,1':3', 1" -terphenyl ] -4-amine) in place of di ([1,1' -biphenyl ] -4-yl) amine (yield 60%).
m/z：805.30(100.0％)、806.30(65.8％)、807.30(21.4％)、808.31(4.7％)
Example 19: synthesis of Compound 19
Compound 19 was synthesized in the same manner as compound 1 using N- (4- (phenanthren-9-yl) phenyl) - [1,1' -biphenyl ] -4-amine (N- (4- (phenylanthren-9-yl) phenyl) - [1,1' -biphenyl ] -4-amine) instead of di ([1,1' -biphenyl ] -4-yl) amine (yield 63%).
m/z：829.30(100.0％)、830.30(68.0％)、831.30(22.8％)、832.31(5.2％)
Example 20: synthesis of Compound 20
Compound 20 was synthesized in the same manner as compound 1 using N- ([1,1' -biphenyl ] -4-yl) triphenylen-2-amine (N- ([1,1' -biphenyl ] -4-yl) triphenylen-2-amine) instead of di ([1,1' -biphenyl ] -4-yl) amine (yield 64%).
m/z：803.28(100.0％)、804.29(65.4％)、805.29(21.4％)、806.29(4.7％)
Examples 21 to 40: preparation of organic light-emitting device
Example 21
By ultrasonic pairing of distilled water
The glass substrate coated with Indium Tin Oxide (ITO) into a thin film was washed. After the completion of the distilled water washing, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, transferred to a plasma cleaner, cleaned with oxygen plasma for 5 minutes, and then deposited on the indium tin oxide substrate as a hole injection layer by a thermal vacuum deposition apparatus (thermal evaporator)
HI01, preparing a film
The HATCN of (2) is formed as a hole transport layer
HT01 (g) as a light-emitting auxiliary layer
The light-emitting layer was doped with 3% BH 01: BD01, to
Film formation is performed. Then, as an electron transport layer
ET 01: liq (1: 1) is subjected to film formation, and then
LiF, and,
The device was sealed in a glove box (Encapsulation) to prepare an organic light emitting device.
Examples 22 to 40
An organic light-emitting device fabricated by using compounds 2 to 20 in place of compound 1 was prepared in the same manner as in example 21.
Comparative examples 1 to 11
An organic light-emitting device manufactured by using ref.1 to ref.11 instead of compound 1 was prepared in the same manner as in example 21.
Performance evaluation of organic light-emitting device
The organic light emitting devices of examples 21 to 40 and comparative examples 1 to 11 were evaluated for performance by applying a voltage to inject electrons and holes using a gishley 2400 source measurement unit (kinetey 2400 source measurement unit), measuring luminance at the time of light emission using a Konica Minolta (Konica Minolta) spectroradiometer (CS-2000), and thus measuring current density and luminance with respect to the applied voltage under atmospheric pressure conditions, and the results thereof are shown in the following table 2.
[ Table 2]
| Op.V | mA/cm2 | Cd/A | QE(％) | CIEx | CIEy | LT95 | |
| Example 21 | 3.6 | 10 | 8.0 | 7.0 | 0.140 | 0.109 | 200 |
| Example 22 | 3.6 | 10 | 7.4 | 6.6 | 0.139 | 0.110 | 170 |
| Example 23 | 3.6 | 10 | 7.4 | 6.7 | 0.140 | 0.111 | 172 |
| Example 24 | 3.7 | 10 | 7.6 | 6.7 | 0.140 | 0.110 | 190 |
| Example 25 | 3.7 | 10 | 7.5 | 6.6 | 0.142 | 0.110 | 192 |
| Example 26 | 3.8 | 10 | 7.6 | 6.8 | 0.140 | 0.111 | 190 |
| Example 27 | 3.7 | 10 | 8.1 | 6.9 | 0.141 | 0.110 | 192 |
| Example 28 | 3.6 | 10 | 8.0 | 7.0 | 0.140 | 0.109 | 197 |
| Example 29 | 3.7 | 10 | 7.9 | 6.8 | 0.141 | 0.110 | 185 |
| Example 30 | 3.7 | 10 | 7.8 | 6.8 | 0.140 | 0.110 | 186 |
| Example 31 | 3.9 | 10 | 8.4 | 7.0 | 0.139 | 0.111 | 185 |
| Example 32 | 3.9 | 10 | 8.3 | 7.0 | 0.140 | 0.110 | 184 |
| Example 33 | 4.0 | 10 | 8.4 | 7.1 | 0.141 | 0.111 | 179 |
| Examples34 | 4.0 | 10 | 8.3 | 7.0 | 0.140 | 0.111 | 180 |
| Example 35 | 3.7 | 10 | 7.3 | 6.4 | 0.140 | 0.110 | 170 |
| Example 36 | 3.6 | 10 | 7.9 | 6.8 | 0.140 | 0.110 | 190 |
| Example 37 | 3.6 | 10 | 8.1 | 7.0 | 0.140 | 0.110 | 199 |
| Example 38 | 3.7 | 10 | 8.4 | 7.2 | 0.140 | 0.110 | 205 |
| Example 39 | 3.8 | 10 | 7.9 | 6.8 | 0.140 | 0.110 | 197 |
| Example 40 | 3.7 | 10 | 7.9 | 6.7 | 0.140 | 0.111 | 196 |
| Comparative example 1 | 4.2 | 10 | 6.7 | 5.6 | 0.140 | 0.111 | 105 |
| Comparative example 2 | 4.5 | 10 | 6.5 | 5.6 | 0.141 | 0.110 | 95 |
| Comparative example 3 | 4.3 | 10 | 6.5 | 5.3 | 0.140 | 0.110 | 100 |
| Comparative example 4 | 4.7 | 10 | 6.1 | 5.1 | 0.142 | 0.112 | 41 |
| Comparative example 5 | 4.9 | 10 | 6.0 | 5.1 | 0.140 | 0.112 | 57 |
| Comparative example 6 | 4.4 | 10 | 6.8 | 5.4 | 0.141 | 0.111 | 85 |
| Comparative example 7 | 4.5 | 10 | 6.7 | 5.3 | 0.140 | 0.110 | 80 |
| Comparative example 8 | 4.4 | 10 | 6.8 | 5.4 | 0.140 | 0.110 | 110 |
| Comparative example 9 | 4.3 | 10 | 6.7 | 5.3 | 0.140 | 0.111 | 105 |
| Comparative example 10 | 4.2 | 10 | 7.0 | 5.7 | 0.140 | 0.110 | 117 |
| Comparative example 11 | 4.2 | 10 | 7.0 | 5.7 | 0.140 | 0.110 | 120 |
As shown in table 2, it was confirmed that examples 21 to 40 using the compound of the present invention as a light-emitting auxiliary layer had improved efficiency and life compared to comparative examples 1 to 11.
More specifically, dibenzofuran in examples 21 to 40 was linearly linked with tricyclic condensed-ring dibenzothiophene, fluorene or dibenzofuran, compared to comparative examples 1, 2, thereby having fast Hole mobility (Hole mobility) to achieve low voltage characteristics.
Further, dibenzofuran in examples 21 to 40 was combined with tricyclic condensed ring dibenzothiophene, fluorene or dibenzofuran to form a deep HOMO, compared to comparative example 3, and thus, may have excellent efficiency.
Also, examples 21 to 40 include a linker between the nitrogen of dibenzofuran and arylamine to form deep HOMO and have fast hole mobility by increasing pi conjugation, compared to comparative examples 4 and 5, thereby realizing low voltage characteristics.
In addition, in examples 21 to 40, compared to comparative examples 6, 7, 8, and 9, the 2 nd or 4 th position of dibenzofuran, which has excellent electron resistance and small bulk property (bulkiness), is bonded to nitrogen of arylamine through a linker, thereby maintaining HOMO and high LUMO that are easy to transport holes, improving the film alignment between molecules, and suppressing the roll-off phenomenon by improving mobility in the film, thereby improving the lifetime.
Also, nitrogen in examples 21 to 40 has dibenzofuran on one side and an aryl group having 12 or more carbon atoms on the other side, as compared with comparative examples 10, 11, whereby pi conjugation can be increased and hole mobility can be improved, thereby exhibiting results indicating low voltage characteristics.
Also, examples 27 and 38, which include a phenylene group having a meta bond, have a deeper HOMO, thereby further improving efficiency and lifetime.
The above description of the present invention is intended to be illustrative, and it will be understood by those skilled in the art that the present invention may be easily modified in other specific forms without changing the technical spirit or essential features of the present invention. It is therefore to be understood that the above described embodiments are illustrative in all respects, rather than restrictive. For example, each component described as a single embodiment may be implemented as a dispersion, and similarly, a plurality of components described as a dispersion may be implemented as a combination.
The scope of the present invention is indicated by the appended claims rather than the foregoing detailed description, and all changes and modifications that come within the meaning and range of equivalency of the claims are to be construed as being included therein.
Description of reference numerals
100: substrate
200: hole injection layer
300: hole transport layer
400: luminescent layer
500: electron transport layer
600: electron injection layer
1000: anode
2000: and a cathode.
Claims (20)
1. A compound represented by the following chemical formula 1;
chemical formula 1
In the chemical formula 1, the first and second organic solvents,
x is O, S or CRR',
Ar1is substituted or unsubstituted C6～C50Aryl of (2), or substituted or unsubstituted C5～C50The heteroaryl group of (a) is a group,
Ar2is substituted or unsubstituted C12～C50The aryl group of (a) is,
R、R`、R1to R6Each independently hydrogen, halogen, nitro, nitrile, substituted or unsubstituted C1～C30Alkyl, substituted or unsubstituted C2～C30Alkenyl of (a), substituted or unsubstituted C1～C30Alkoxy, substituted or unsubstituted C1～C30Sulfide group, substituted or unsubstituted C6～C30Aryl of (2), or substituted or unsubstituted C5～C30Heteroaryl of (a), adjacent multiple R1Between, a plurality of R2Between, a plurality of R3Or R and R' may be bonded to each other to form a ring or not, R4And R6Or R5And R6Can be combined to form a ring or not form a ring,
L1is a direct bond, substituted or unsubstituted C6～C30Or substituted or unsubstituted C5～C30The heteroarylene group of (a) is,
L2is substituted or unsubstituted C6～C30Or substituted or unsubstituted C5～C30The heteroarylene group of (a) is,
l is 0 or an integer from 1 to 4,
m and n are each independently 0 or an integer of 1 to 3,
when l, m or n is more than 2, R1、R2And R3Can each be the same or different.
2. The compound of claim 1, wherein the compound is represented by the following chemical formula 2;
chemical formula 2
In the chemical formula 2,
X、Ar1、Ar2、R、R`、R1to R6、L1L, m and n are as defined in said chemical formula 1,
R7is hydrogen, halogen, nitro, nitrile, substituted or unsubstituted C1～C30Alkyl, substituted or unsubstituted C2～C30Alkenyl of (a), substituted or unsubstituted C1～C30Alkoxy, substituted or unsubstituted C1～C30Sulfide group, substituted or unsubstituted C6～C30Aryl of (2), or substituted or unsubstituted C5～C30The heteroaryl group of (a) is a group,
o is an integer of 1 to 4, p is 0 or an integer of 1 to 4, and when o or p is 2 or more, R is7Can be the same or different, and when o is 2 or more, p can be the same or different.
3. The compound of claim 1, wherein the compound is represented by the following chemical formula 3;
chemical formula 3
In the chemical formula 3, the first and second organic solvents,
X、Ar1、Ar2、R、R`、R1to R6L, m and n are as defined in said chemical formula 1,
R7is hydrogen, halogen, nitro, nitrile, substituted or unsubstituted C1～C30Alkyl, substituted or unsubstituted C2～C30Alkenyl of (a), substituted or unsubstituted C1～C30Alkoxy, substituted or unsubstituted C1～C30Sulfide group, substituted or unsubstituted C6～C30Aryl of (2), or substituted or unsubstituted C5～C30The heteroaryl group of (a) is a group,
o is an integer from 1 to 4, p is 0 or an integer from 1 to 4,
when o or p is 2 or more, R7Can be the same or different, and when o is 2 or more, p can be the same or different.
4. The compound according to claim 1, wherein the compound is represented by the following chemical formula 4 or chemical formula 5;
chemical formula 4
Chemical formula 5
In the chemical formulas 4 and 5,
Ar1、Ar2、R1to R6L and n are as defined in said chemical formula 1,
x is O or S, and X is O or S,
R2can be the same or different and can be,
R7is hydrogen, halogen, nitro, nitrile, substituted or unsubstituted C1～C30Alkyl, substituted or unsubstituted C2～C30Alkenyl of (a), substituted or unsubstituted C1～C30Alkoxy, substituted or unsubstituted C1～C30Sulfide group, substituted or unsubstituted C6～C30Or substituted or unsubstituted aryl ofSubstituted C5～C30The heteroaryl group of (a) is a group,
o is an integer from 1 to 4, p is 0 or an integer from 1 to 4,
when o or p is 2 or more, R7Can be the same or different, and when o is 2 or more, p can be the same or different.
5. The compound according to claim 1, wherein the compound is represented by the following chemical formula 6;
chemical formula 6
In the chemical formula 6, the first and second organic solvents,
Ar1、Ar2、R、R'、R1to R6L, m and n are as defined in said chemical formula 1,
R7is hydrogen, halogen, nitro, nitrile, substituted or unsubstituted C1～C30Alkyl, substituted or unsubstituted C2～C30Alkenyl of (a), substituted or unsubstituted C1～C30Alkoxy, substituted or unsubstituted C1～C30Sulfide group, substituted or unsubstituted C6～C30Aryl of (2), or substituted or unsubstituted C5～C30The heteroaryl group of (a) is a group,
o is an integer from 1 to 4, p is 0 or an integer from 1 to 4,
when o or p is 2 or more, R7Can be the same or different, and when o is 2 or more, p can be the same or different.
6. The compound according to claim 1, wherein the compound is represented by the following chemical formula 7 or chemical formula 8;
chemical formula 7
Chemical formula 8
In the chemical formulas 7 and 8,
Ar1、Ar2、R1to R6L and n are as defined in said chemical formula 1,
x is O or S, and X is O or S,
R2can be the same or different and can be,
R7is hydrogen, halogen, nitro, nitrile, substituted or unsubstituted C1～C30Alkyl, substituted or unsubstituted C2～C30Alkenyl of (a), substituted or unsubstituted C1～C30Alkoxy, substituted or unsubstituted C1～C30Sulfide group, substituted or unsubstituted C6～C30Aryl of (2), or substituted or unsubstituted C5～C30The heteroaryl group of (a) is a group,
o is an integer from 1 to 4, p is 0 or an integer from 1 to 4,
when o or p is 2 or more, R7Can be the same or different, and when o is 2 or more, p can be the same or different.
7. A compound of claim 1, wherein R is1To R6Each independently hydrogen or phenyl.
8. A compound according to any one of claims 2 to 6, wherein R is1To R7Each independently hydrogen or phenyl.
9. A compound according to any one of claims 1 to 3 or 5, wherein R and R' are each independently C1～C3Alkyl group of (1).
10. A compound according to any one of claims 1 to 4 or 6, wherein X is O.
11. A compound according to any one of claims 1 to 4 or 6, wherein X is S.
12. The compound according to any one of claims 1 to 6,
ar is1Selected from the group consisting of phenyl, naphthyl, biphenyl, terphenyl, fluorenyl, dialkylfluorenyl, diarylfluorenyl, dibenzofuranyl, dibenzothienyl, and combinations thereof,
ar is2Selected from the group consisting of biphenyl, phenylnaphthyl, terphenyl, fluorenyl, dialkylfluorenyl, diarylfluorenyl, dibenzofuranyl, dibenzothienyl, and combinations thereof.
13. The compound of claim 1, wherein L is2Is a substituted or unsubstituted C comprising at least one 1, 4-phenylene or 1, 3-phenylene group6～C24An arylene group of (a).
14. The compound according to any one of claims 1 to 6,
ar is1Selected from the group consisting of phenyl, biphenyl, terphenyl, dimethylfluorenyl, and combinations thereof,
ar is2Selected from the group consisting of biphenyl, terphenyl, dimethylfluorenyl, and combinations thereof.
15. The compound of claim 1, wherein Ar is Ar1、Ar2And L2Comprises a phenylene group having a meta linkage.
16. According to the rightThe compound of claim 15, wherein Ar is1Is biphenyl group having a meta linkage or terphenyl group having a meta linkage, or the Ar2Is biphenyl with meta bonding or terphenyl with meta bonding.
17. The compound according to any one of claims 1 to 6, wherein one or more of the following a) to c) are satisfied:
a)Ar1and Ar2Is biphenyl;
b)Ar1and Ar2At least one of which is C consisting of a six-membered ring14The above aryl group; and
c)L2is C10The arylene group above.
18. The compound of claim 1, wherein the compound is one of the following compounds,
19. an organic light-emitting device characterized by comprising an organic layer containing the compound according to any one of claims 1 to 6 between a first electrode and a second electrode.
20. The organic light-emitting device according to claim 19, wherein the organic layer is one or more of a hole injection layer, a hole transport layer, and a light-emission auxiliary layer.
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| KR10-2018-0037638 | 2018-03-30 | ||
| PCT/KR2019/003723 WO2019190270A1 (en) | 2018-03-30 | 2019-03-29 | Novel compound and organic light-emitting device comprising same |
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| WO2014042420A1 (en) * | 2012-09-14 | 2014-03-20 | Rohm And Haas Electronic Materials Korea Ltd. | A novel organic electroluminescence compound and an organic electroluminescence device containing the same |
| WO2017119792A1 (en) * | 2016-01-07 | 2017-07-13 | 주식회사 엘지화학 | Compound and organic electronic element comprising same |
| WO2017196081A1 (en) * | 2016-05-11 | 2017-11-16 | Sk Chemicals Co., Ltd. | Compound for organic electroluminescent device and organic electroluminescent device comprising the same |
| CN107667099A (en) * | 2015-05-06 | 2018-02-06 | 东进世美肯株式会社 | Compounds and the organic luminescent device for including it |
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| KR101792908B1 (en) * | 2014-05-26 | 2017-11-02 | 주식회사 엘지화학 | Hetero-cyclic compound and organic light emitting device comprising the same |
| EP3423542B1 (en) * | 2016-03-03 | 2020-07-22 | Merck Patent GmbH | Materials for organic electroluminescent devices |
| KR20170127353A (en) * | 2016-05-11 | 2017-11-21 | 에스케이케미칼주식회사 | Compound for organic electroluminescent device and organic electroluminescent device comprising the same |
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| WO2014042420A1 (en) * | 2012-09-14 | 2014-03-20 | Rohm And Haas Electronic Materials Korea Ltd. | A novel organic electroluminescence compound and an organic electroluminescence device containing the same |
| CN107667099A (en) * | 2015-05-06 | 2018-02-06 | 东进世美肯株式会社 | Compounds and the organic luminescent device for including it |
| WO2017119792A1 (en) * | 2016-01-07 | 2017-07-13 | 주식회사 엘지화학 | Compound and organic electronic element comprising same |
| WO2017196081A1 (en) * | 2016-05-11 | 2017-11-16 | Sk Chemicals Co., Ltd. | Compound for organic electroluminescent device and organic electroluminescent device comprising the same |
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