TWI374139B - Imidazopyridine-based compound and organic light emitting diode including organic layer comprising the imidazopyridine-based compound - Google Patents

Description

1374139 IX. Description of the invention: [Technical field to which the invention pertains] Cross-reference to related applications This application claims Korean patents filed at the Korea Intellectual Property Office on July 24, 2006 and February 24, 2006, respectively. Priority and benefit of Applicants Nos. 2-6-〇1 17092 and 10·2007_0〇74〇97, the entire contents of which are incorporated herein by reference. interest

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an imidazole pyridine-based compound, and an organic light-emitting diode of an organic layer containing an imidazole pyridine-based compound, which is more specific, and the present invention is directed to an organic light-emitting diode (four). An electron-transporting layer of a compound mainly composed of mirazolidine and an organic light-emitting diode containing an organic layer of a compound mainly composed of a pyridoxine. [Prior Art] Background of the Invention A diode having a krypton, a steering voltage, and Organic light-emitting diodes (0LEDs) are excellent contrast ratios for self-luminous wide viewing angles, as well as fast reaction times. In addition, organic light-emitting diodes have good brightness response time and can obtain multi-color images. The polar body is such that 'the anode is formed on the substrate, and the hole transport layer, the light-emitting layer, the electron transport layer, and the cathode are continuously formed on the % electrode. The hole transport layer, the light-emitting layer, and the electron transport layer are organic compound-shaped organic thin films. (4) Luminescence: The polar body has the following structure: When 6 1374139 applies a voltage on the anode and the cathode, the hole injected from the anode passes through the electricity. • The transport layer moves to the light-emitting layer. The electrons injected from the cathode move through the electron transport layer to the light-emitting layer. The holes and electrons recombine with each other in the light-emitting layer to generate an exciton. When the exciter falls from the excited state to the ground state, the light is emitted. The fluorescent molecules of the layer emit light. Heteroaromatic compounds such as oxadiazole thiadiazole, samarium and the like can be used as the material for forming the electron transport layer. However, the conventional organic light-emitting body does not Satisfactory driving voltage, brightness, current intensity, power coefficient, lifetime, and the like. SUMMARY OF THE INVENTION [Invention] According to the present invention, a compound in which a microphone is predominantly has electron-transporting ability. The imidazole pyridine-based compound, low driving voltage, high brightness, and in another embodiment of the present invention, the organic light-emitting diode has a high efficiency and a long life.

The compound according to the specific aspect of the present invention " rice pyridine pyridine comprises a compound represented by the following formula 1. Formula 1

>ν Κιϊ _ . y I f, m stalk n R : an integer from 0 to 4, and ... neither are humming, 2 3 I ' ^ ' I, R7, R8, I, R,. , , and , respectively, selected 1374139 2 atoms, (4) atoms, via groups, cyano groups, substituted C, -c3. a group, a substituted or unsubstituted or unsubstituted W group, a non-substituted C2-C30 alkenyl group, a substituted or unsubstituted alkyne A radical, substituted or unsubstituted hydrazine. Or an unsubstituted c3-c30 heteroaryl group. R4, r a substitutions Two of the two are combined to form a saturated or non-fresh ring. Second and middle to

At least two of and % are combined with each other 9 10, R" and L can be eight.s 6/珉铯 and or unsaturated rings. L| 匕21^ is selected from the group consisting of an early bond, a substituted or unsubstituted group, a substituted or unsubstituted '3◦alkyl group, a C6_C30 pendant group, and a rod-type unsubstituted Hey. Hetero-aryl group. Eight = Ge Substituted or unsubstituted C _C 芸 | culvert 2 knives J is selected from W. Heteroaryl group. a aryl group and a substituted or unsubstituted package: a steroidal state of the 'organic luminescent dipole _ _ _ ^ electrode, and a layer between the first and the :: the organic layer contains a taste saliva . A compound dominated by pyridine. i^ The microphone represented by the formula 1. Sitting η than &&&&&&&&&&&&&&&&&&&&&&&&&&&<RTIgt; ...Density, High Brightness, High Efficiency [Embodiment] Detailed Description of the Invention Mainly on the other hand: Document 1 shows that imidazolium is not a compound according to the specific aspect of the present invention.

8 1374139

To the ’ show ‘... in the first to eighth positions of the onion ring 〉 one place instead of the ninth or tenth position of the ring with the taste... " rice bran. The 唆 ring is not bonded to the 帛9 or the first 葱 position of the onion ring because the 9th and 10th positions are structurally weak points. Therefore, when the ninth and the ninth ring of the anthracene ring are replaced by a group having a specific function! It is easy to combine organic light-emitting two-body by heat, [moisture or the like, and with Huihuan Mi (four) material (which is electron-deficient) and the 9th stand of the first ring. The organic layer of (OLED) (eg, by deposition or the like) is produced; the door, the bite ring and the onion ring decompose. In the operation of the organic light-emitting diode J, it is also possible to make glutinous rice 0 sit

The characteristics of the diode deteriorate. ^ :..., "This organic light-based compound; aryl = this hair: the specific aspect (4) The 9th or 1st square group or the heterocyclic group position of the group and the anthracene ring, s. , the imidazole pyridine ring (its IS) and at least - the binding factor mobility of the first to eighth positions of the anthracene ring. The main compound may have improved structural properties and electricity. ^ r! 'Λ ^ &quot ;3;R; 'Re'R?'Rs'R9'R- ° ' Group' substituted or unsubstituted c minus group, aryl-based crC30 alkyl group, substituted or not 1374139 C, C3° said a base group, a substituted or unsubstituted cvc30 acid disubstituted unsubstituted anthracene. Alkenyl function, substituted or aryl-based 2 2 alkynyl group, substituted Or unsubstituted R- or unsubstituted 匕-~heteroaryl group. R4, at least two of the 6# I are bonded to each other to form a saturated or unsaturated group, and R, At least two of ρ η ^ 9 l〇, R, j〇 are bonded to each other to form a saturated or unsaturated ring. / In a specific aspect, R to R may be VIII., substituted or unsubstituted cvc II 7 is selected from a hydrogen atom and is taken from C Γ ^ 1 10 alkyl group, substituted or unsubstituted 2 10 alkenyl group, substituted or unsubstituted c; c Α _ substituted or unsubstituted cvc, 2 heteroaryl group / a group and a "root: another - specific aspect, at least two of ^, ..., today: at least two of l〇U and R|2' combine to form a substituted or unsubstituted c6_c, 2 Aromatic ring. W is taken in Formula 1, and 1^ and l2 are respectively selected from a single bond,

a substituted alkyl group of 5, a substituted, unsubstituted or unsubstituted cr Ab # group and a C3-C3G heterodyne substituted with or without 6 Μ Base group. In one embodiment, LA L2 may be selected from a substituted or unsubstituted C12-aryl group and a substituted C6- group, respectively. The substituted or unsubstituted cc, 2 heteroaryl group CC can be selected from the group consisting of a substituted or unsubstituted 6 3 ° square group and a substituted or unsubstituted c 分别, respectively. group. In a specific aspect, for example, oxime and & 2 == aryl or unsubstituted C6-Cl2 j is selected from substituted 12-valent group and substituted or unsubstituted c3- 1374139 ci2 The aryl group β In the formula 1, Ρ and q are respectively selected from the i to 5 body state, an integer of 丨k . In a τ such as Ρ and q are from 1 to 3, respectively, slave u have at least one D4i & king number. That is to say, the chemical structure of a sulfazole ring can be combined with L or L2. It can be, or can be in the form 1 towel, the claws and n are respectively selected from the 〇 to η, especially the work, but the work and the saliva:: that is, in the bite based on the specific aspect of the present invention In the compound, at least some of the i- to-position of the onion ring is bound to the imidazole pyridine ring. In a specific aspect, θ Λ 〜 γ, for example, m may be 疋, and n may be 1. In another specific sample Wherein, L 铱肀, m and η can be both 匕疋 1 〇 in the compound represented by Formula 1, using the appropriate unsubstituted c "c3. Non-limiting examples of the phenotypic group A methyl group, an ethyl group, a propyl group, an isobutyl group, a second-butyl group, a pentyl group, an iso-pentyl group, a hexyl group, and the like are included. Using a group selected from the group consisting of a (iv) atom, a thiol group, a nitro group, a cyano group, an amine group, a thiol group, a carboxy group or a salt thereof, a chloric acid group or a salt thereof, Phosphate group or a salt thereof, CVCw alkyl group, c2_c3 nonenyl group, C2_c3 decynyl group, CVCm aryl group, C7_C2 fluorene aralkyl group, C2_C2 〇 aryl group The substituent of the G-Cm heteroaralkyl group is substituted for at least one hydrogen atom of the alkyl group. In the case of the compound represented by Formula 1, the appropriate unsubstituted c, -C3 nonyloxy group is used. Non-limiting examples of groups include methoxy groups, ethoxy groups, phenoxy groups, cyclohexyloxy groups, naphthyloxy groups, isopropyl 1374139 oxy groups, dioxane a group and the like. At least one hydrogen atom of the alkoxy group may be substituted with a substituent selected from the above in connection with the c, -c30 alkyl group. In the compound represented by Formula 1, Non-limiting examples of suitable unsubstituted C"C3Q Si-based groups used include (10) a group of a group of a group, an isopropyl group, a benzyl group, a naphthyl group, a diphenylenyl group, a cyclohexylcarbonyl group, and the like. The stomach kappa 3 may be substituted with a substituent selected from the above in connection with the G-C3. alkyl group. At least one hydrogen atom of the brewing group In the compound represented by Formula 1, the appropriate unsubstituted C2-C3 is used. Non-limiting examples of the dilute group are included above. a compound having a carbon-carbon double bond in the middle or at the end of the defined pendant group. For example, the unsubstituted C2-C30 dilute group may be selected from an ethylene group, an acryl group, a butadiene group, A hexamidine group and the like. At least one hydrogen atom of the alkenyl group may be substituted with a substituent selected from the above in connection with the group.

In the compound represented by Formula 1, a non-limiting example of a suitably unsubstituted qc" alkynyl group used includes a compound having a carbon-carbon triple bond in the middle or at the end of the above group. For example, The two: c2-c3G fast radical group may be selected from the group consisting of an ethyl group, a propyl group, a phenethyl group, a naphthylethyl group, an isopropylacetylene group, and a third τ group. a group of diphenylethynyl groups and the like. At least one of the alkynyl groups selected from the substituents discussed above in connection with the alkyl group may be substituted with a compound represented by formula 1 Suitable unsubstituted 12 1374139 c6-c3 used. Non-limiting examples of aryl groups include -c3. Carbocyclic aromatic systems. At least one aromatic ring = v two fused to each other, or borrowed The oxime in which the single bonds are bonded to each other, or the like, may be substituted with at least one hydrogen atom of the 5-nonyl group selected from the substituents discussed above in connection with the CVC3G alkyl group.

Substituted or unsubstituted c6_c3. The aryl group may be selected from a phenyl group, a C^-Cm alkane group (e.g., an ethylphenyl group), a kappa(7) alkyl diphenyl group (e.g., an ethyldiphenyl group), and a halogen. a phenyl group (eg, o-, m- and p-fluorophenyl groups and a di-phenyl group), a dicyanophenyl group, a tris-methoxyphenyl group, an o--inter- and p-Phenylphenyl group, o-, m- and p-anisyl groups, 2,4,6-triphenylene group, oxyphenyl group, (α,α-dibenzyl)benzene Base group, (Ν,Ν,_dimethyl)amine phenyl group, (ν,ν,_diphenyl)amine phenyl group, cyclopentenyl group, segment base a group, a naphthyl group, a halophthyl group (e.g., a fluoronaphthyl group), a Ci_Ci decylene group (e.g., a methylnaphthyl group), a CrCi decyl oxynaphthyl group (e.g., methoxy) Naphthyl group), mercapto group, base group, mercapto group, terpene naphthyl group, mercapto group, mercapto group, mercapto group, mercapto group, Fenyl group, triphenylene group, pyrenyl group, chrysenyl group, ethyl-fast a group, an emisyl group, a pherylenyl group, a chlorophenanthrenyl group, a pentaphenyl group, a pentacenyl group, a tetraphenyl group, a hexa Stupid group, hexaphenyl group, tea base (rubicenyG group, cor〇nenyi group, hydrazine group, heptyl group, heptaphenyl group, η Pyranthrenyl group, ovalenyl group, and the like. 13 1^/4.139

In the compound of m, non-limiting examples of suitable unsubstituted 3·3 fluorene aryl groups used include at least one family of rings including at least one hetero atom selected from N, 0, 〜s. The remaining ring members are carbon systems and systems. The at least one aromatic ring may be at least two rings fused to each other, or bonded to each other by a single bond, or the like. can

At least one hydrogen atom of the heteroaryl group is substituted with a substituent selected from the above in connection with an alkyl group. A non-limiting examples of suitably substituted unsubstituted q-Cu heteroaryl groups used in the compound of the formula include pyrazolyl groups, imidazolyl groups, yl groups, (iv) groups , trisalyl group, four. Sit group, oxadiazolyl group, pyridyl group, hydrazine group, pyrimidinyl group, tri-cultivating group, carbazolyl group, fluorenyl group, quinolyl group Groups, isoquinolyl groups and the like. Non-limiting examples of substituents suitable as R to Ru of formula 1 include a hydrogen atom, a cvc1 () alkyl group, a Ci_Ci 〇 haloalkyl group, a C2_Ci decenyl group, a C2-Cl0 haloalkenyl group. a group, a phenyl group, a halo group, an alkylphenyl group, a Ci-Cw alkoxyphenyl group, a naphthyl group, a halonaphthyl group, a Crci() naphthyl group And a Ci-Cw alkoxynaphthyl group. Non-limiting examples of substituents suitable as L of formula 1, and L2 include a phenylene group, a halogenated phenyl group, a CrC|decyl phenyl group, a CrCl0 alkoxyphenyl group, An anthranyl group, a halo-naphthyl group, a CrClO-alkylnaphthyl group, and a Ci_C|nonalkyloxynaphthyl group. Non-limiting examples of substituents suitable as exemplified for Formula 1 VIII 1* and Ar. 2 include a phenyl group, a halophenyl group, a Ci_Ci decyl phenyl group, and a u/4.139 phenoxy group. 'Naphthyl group, halophthyl group, Cl-c10 alkynyl group, Ci-Ci0 alkoxynaphthyl group, pyridyl group, halopyridyl group, C|_C|. Pyridyl group pyridine group, C1-Cl() alkoxypyridyl group, quinolyl group, haloquinolinyl group, c,-c10 alkylquinolyl group, crc10 alkoxy a quinolinolyl group, an isoquinolyl group, a dentate isoquinolyl group, a crc1()alkylisoquinolyl group, and a c,-cl()alkoxyisoquinolyl group. In a specific cancer sample, la, lb, lc, and Id can be expressed as 0 m. More than a bite-based compound.

La

15 1374139 lc

Non-limiting examples of compounds suitable for use as the imidazopyridine-based compound represented by Formula 1 include the following compounds 1 to 11.

16 1374139 Compound 1 Compound 2

17 1374139 Compound 6

18 1374139 Compound 11

A compound represented by Formula 3 is a compound represented by Formula 4, and both of them are shown below, and a compound of the formula Imidazopyridine represented by Formula 1 is obtained. Equation 2

n[(H〇)2B]

formula

Equation 4

The imidazopyridine-based compound represented by VIII. According to a specific aspect of the present invention, a taste saliva represented by the formula 可 can be used. ratio

(S 19 1374139

The compound 'forms' forms an organic layer of an organic light-emitting diode. In the case of an I, for example, an organic light-emitting diode comprises an organic layer of a first electrode and an imidazole pyridinium represented by the formula 1 between the first and second electrodes, ± ^ Jh ^ 3 . The pyridine is a specific aspect of the worker's finger. The organic layer can be a β-sub-transport layer. Organic light-emitting diode-hole transport layer, electron-resisting layer, light-emitting layer, electricity second, main entry layer, electric layer, electron injection layer and "and the barrier layer and the electron transmission mouth are more than the mouth 2:: For example, when the organic layer containing the formula of the formula 1 is an electron transporting reed 0#, the austenitic light-emitting diode may further comprise s organic electrons/input layer. Further, when the luminescent layer is When the phosphorometer LED light-emitting diode can be further formed, there are various other structures. The organic light-emitting body illustrated in the circle 1 of the organic light-emitting diode according to one embodiment of the present invention is explained. The diode has a first electrode/hole

The structure of the injection layer/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/second electrode. However, it should be understood that the organic light emitting diode is not limited to this structure, and may have various other structures, b first electrode / hole injection layer / light emitting layer / electron transfer layer / electron injection layer / second electrode structure, Or the structure of the first electrode/hole left layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron main entry layer/second electrode. The electron transport layer may be formed of a compound mainly composed of pyridine represented by the formula °. According to an embodiment of the present invention, the light-emitting layer of the organic light-emitting diode may comprise a red, green, blue or white phosphorescent or fluorescent dopant. The phosphorescent dopant may be an organometallic compound selected from the group consisting of Ir, pt, 〇s, Ti, Zr, and 20 丄.

Hf, Eu, Tb, Tm are metals of the group m and its combination. In the following text, the old organic light-emitting device explained in Fig. 1 will be described in the same manner as the organic light-emitting diode according to the present invention and n-green and eight-body-like organic light-emitting diodes. Methods. =, hunting to deposit a material with a high work function or (10) forming a dipole-electrode on a substrate. The first electrode can be an anode or a cathode. The substrate may be any substrate used for the # mu used in the organic light-emitting device, and may be a glass substrate or a transparent plastic substrate, which may be easily handled by the county, is waterproof, and has Excellent mechanical strength, thermal stability, transparency and surface smoothness. The first electrode may be formed of ITO, IZO, Sn〇2, Zn0 or any transparent material having high conductivity. Next, a hole injection layer (HIL) can be formed on the first electrode by real mining film, spin coating, wash, Lanmuir Blodgett (LB) deposition or the like. When a vacuum coating is formed to form mL, the vacuum coating conditions may vary depending on the compound used to form the HIL, and the desired structure and thermal properties of the hil to be formed. However, vacuum coatings are typically available at temperatures ranging from about 1 00 c to about 500 t: mineral film temperatures ranging from about 1 〇 _8 to about 1 〇 3 Torr (mm Hg), ranging from about 〇.〇. It is carried out at a coating speed of 1 to about 100 A/sec. The thickness of the vacuum coating layer can range from about 10A to about 5 microns. When hil is formed by spin coating, the coating conditions may vary depending on the desired structure and thermal characteristics of the compound which forms the HIL and the HIL to be formed. However, typically the coating speed can range from about 2,000 to about 5, rpm, and the temperature of the heat treatment (which is performed after coating to remove the solvent) can range from about 80 to about 200 °C. 21 1374139 The HIL material is not particularly limited and may be any material known to form HILs. Non-limiting examples of suitable HIL materials include phthalocyanine compounds (such as copper phthalocyanine), star amine derivatives (such as TCTA (shown below), meta-MTDATA (shown below) and meta-MTDAPB), soluble and soluble Conductive polymers (eg polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS) ), polyaniline/camphorsulfonic acid (Pani/CSA), (polyaniline)/poly(4-styrenesulfonate) (PANI/PSS), and the like.

The thickness of the HIL can range from about 100 to about ΙΟ, ΟΟΟΑ. In a particular aspect, for example, the thickness can range from about 100 to about 1, 〇〇〇 A. When the thickness of the HIL is within the above range, the HIL has excellent hole injecting ability, and an organic light-emitting diode having an excellent driving voltage can be obtained. A hole transport layer (HTL) can be formed on the HIL by vacuum coating, spin coating, casting, LB deposition or the like. When the HTL is formed by vacuum coating or spin coating, the conditions of coating and coating are similar to those for forming HIL, although the coating or coating conditions may vary depending on the material used to form the HTL. 22 1374139 There are no special restrictions on HTL materials, and muscle materials. Suitable materials are known to be used as non-limiting examples of machi, including carbazole-derived aromatic/stupid saliva and polyethylene-salt, typical amine derivatives, and; Ν^]-like diphenyl BenZydine (a-NPD is shown below)), and

TPD A - J 1 ~ VIII. J eight to the hole about 1,000 A. In a specific aspect, for example, the thickness is in the range of from about 1 Torr to about _a. When the thickness of the HTL is within the above range, the muscle has a good hole transporting ability, and an organic light-emitting device having an excellent driving voltage can be obtained by vacuum coating, spin coating, washing, LB deposition or the like. The light-emitting layer (EML) is formed on the HTL. When the leg 1 is formed by vacuum film or spin coating, the conditions of the recording film and the coating are similar to those of the shape "HIL, although the forging film and coating conditions can be formed according to The material of EML changes. The luminescent layer can be formed from various known luminescent materials and can include known bodies and dopants. The dopant can be a known fluorescent dopant or a known phosphorescent dopant. Non-limiting examples of suitable host materials include Alqs, 4,4'-mail'-dicarbazole-diphenyl (CBp), poly(positive vinyl group 23, 4139 saliva) (P VK), and stupid Ethylene aryl (DS A), and the like. Non-limiting examples of suitable fluorescent dopants include IDE 102 and IDE 105 from idemitsu c. Non-limiting examples of suitable phosphorescent dopants include green phosphorescent dopants (eg, Ir(ppy) 3 (ppy is an abbreviation for phenylpyridine), (4,6-F2pPy) 2irpic, obtained from c〇vi〇n , TEB002 of Ltd.), red dish light dopant (such as octaethylporphyrin platinum (n) (Pt〇Ep)), a compound represented by the following formula 5, Firpric, TBPe, and the like.

The dopant may be present in an amount ranging from about 〇1 to about 2 〇 by weight based on 100 parts by weight of the total weight of the luminescent layer (that is, the total weight of the host and the dopant). In one embodiment, the dopant is present in an amount ranging from about 0 5 to about 12 parts by weight. The presence of dopants is increased when the dopant is present in excess of about 〇1 by weight. Further, when the amount of the phosphorescent or fluorescent dopant is less than about 20 parts by weight, the concentration is substantially prevented from being quenched. 24 1374139 EML thicknesses range from approximately 1 〇〇 to approximately 1 〇〇〇A. In a physical form, for example, the thickness ranges from about 200 to about 600 Å. When the thickness of the s EML is within the above range, the EML has excellent light-emitting potential, and an organic light-emitting diode having an excellent driving voltage can be obtained.

When the EML includes a phosphorescent dopant, a hole blocking layer (HBL) can be formed on the EML to prevent the triple excitons or holes from moving to the electron transport layer (etl) (not shown in Figure 1). The hbl material is not particularly limited and may be any material known to form HBLs. Non-limiting examples of suitable hbl materials are the two money organisms, the three reading organisms, the phenoline derivatives, Balq, BCP, and the like. The thickness of hbl can range from about 5 〇 to about 1 〇〇〇A. In a specific body, for example, the thickness ranges from about 丨〇〇 to about 3 。. When the thickness of the s HBL is within the above range, the HBL has excellent hole blocking ability, and an organic light-emitting diode having an excellent driving voltage can be obtained. The electron transport layer can be formed on the HB]L by vacuum coating, spin coating, casting or the like (ETL^ when forming a Ετχ by vacuum coating or spin coating, the conditions of the spear coating are usually the same as the formation of Hil The conditions are similar, although the mineral film or coating conditions may vary depending on the material used to form the ETL. ETL may be formed from a compound mainly composed of imidazopyridine represented by Formula 1. It may also be derived from a quinone derivative such as three (8-wow) >#Acid)Ming (Alq3), TAZ or the like is formed, which is known in the art. The thickness of the ETL can range from about 100 to about 1, 〇〇〇Α. In one (-£) 25 When the thickness of the 'ET' is from about 丨〇〇 to about 5 〇〇 A, the thickness of the ETL is within the above range, the ETL has excellent electron transport capability and organic light having an excellent driving voltage can be obtained. In addition, an electron injection layer (EIL) may be deposited on the ETL. EIL allows it to easily inject electrons from the cathode. : EIL may be formed by LiF, NaC, CsF, Li20, BaO or the like, _ This material is known in the art to form muscles. The coating and coating conditions are generally similar to those for forming the HIL, although they may vary depending on the material used to form the EIL. The thickness of the EIL may range from about i to about 1 Å. In a particular aspect, For example, the thickness is in the range of from about 5 to about 9 Å. When the thickness is within the above range, the EIL has excellent electron injecting ability, and an organic light-emitting diode having an excellent driving voltage can be obtained subliminally. The second electrode can be formed on the EIL by vacuum coating, sputtering or the like. The first electrode can be used as a cathode or an anode. The second electrode can be made of a low work function metal, alloy, conductive compound or Non-limiting examples of materials suitable for the second electrode include [丨, A, Al-U, Ca, Mg-ln, Mg_Ag, and the like. Alternatively, a transparent cathode formed of ITO or IZO may be used to produce Front surface light-emitting diodes. For the purpose of explanation only, it is not intended to limit the scope of the invention, the following synthetic examples detailing synthetic compounds i, 4 and 7 are provided, and the details are made in accordance with the invention. Example of the organic light-emitting diode of the aspect. 26 • <S) 1374139 Synthesis Example 1 Synthesis of Compound 1 Synthesis of Compound 1 by Reaction Scheme 1 below: Reaction Scheme 1

1a

1d

Compound 1 27 1374139 Synthesis of intermediate 1 a 10 g of desert copper (44 mmol) and 8 g of 2-aminoindole (35.8 mmol) were added to 250 ml of bromic acid and the mixture was heated To 65. Hey. The mixture was cooled to room temperature after the gas generation was stopped. The mixture was then added to 1000 ml of 20% aqueous hydrochloric acid and extracted with dichloromethane. The water remaining in the organic layer was removed using anhydrous MgS 4 and the resulting product was dried under pressure. The obtained product (dioxane: n-hexane = 4:1) was purified by column chromatography to afford 7 7 g of intermediate (yield 75%). Synthesis of Intermediate 1 b 10 g of the intermediate la (34.8 mmol) was added to 1 mL of THF dehydrated under nitrogen pressure and the temperature of the mixture was lowered to .7 8 . 0.5 M desertified 2-naphthyl magnesium (10 mmol) was slowly added to the mixture. The temperature of the mixture was increased to room temperature, and the mixture was stirred for 3 hours. An aqueous solution of vaporized ammonium was added to the reacted mixture, and the resulting product was extracted with methylene chloride. The organic layer was dried using anhydrous MgS 4 and the solvent was removed. The mixture obtained therefrom was dissolved with a small amount of diethyl ether. Then, petroleum ether was added to the mixture and stirred for several hours to obtain a solid compound. The obtained solid compound was filtered, and then dried in vacuo to give 179 g of dinaphthyl diol. Under nitrogen pressure, 17.6 g of dinaphthyldiol (32 4 mmol) was dispersed in 200 ml of acetic acid. Then, 53.4 g of potassium iodide (33 mmol) and 58 g of sodium hypophosphite hydrate (660 mmol) were added to the mixture, and 28 1374139 was mixed and returned to "3 hours." The obtained product was cooled to room temperature, dried, washed with water and methanol, and then dried in vacuo to afford i 13 g of pale yellow intermediate lb. Synthesis of Intermediate 1 c 5 g of the intermediate lb (9.81 mmol) was dissolved in 7 mL of THF dried under nitrogen pressure and at -78. 47 ml of butyllithium (n 8 mmol) was added to the mixture under the arm. The mixture was stirred at the same temperature for 1 hour, and then 2.20 ml of trimethyl borate (29 4 mmol) was added to the mixture. The temperature of the mixture was increased to room temperature, and after a few hours, 2N aqueous hydrochloric acid was added to the mixture and stirred for 3 hours. The obtained solid compound was filtered while washing with toluene to obtain 3 · 27 g of pale yellow intermediate lc (yield 70%). Synthesis of intermediate 1 d

Dissolve 3.39 g of 2-aminopyridine (35.98 mmol) and 1 g of 2,4,-di-diethylene oxime (3 5.9 8 Torr) in 150 ml of ethanol and reflux the mixture. 12 hours. The mixture was cooled to room temperature to give a white solid. The resulting white solid was washed with a saturated NaHC solution. The water remaining in the organic layer was removed using anhydrous MgS〇4, dried under reduced pressure, and then recrystallized (dichloromethane/n-hexane) to obtain 8.02 g of intermediate ld having a flaky crystalline form ( Production 82%). Synthesis of Compound 1 1.85 g of a 1p compartment lc (3.90 mmol) and 1 g of an intermediate id (39 mM mmol) were added to a mixed solvent of 2.7 g of an aqueous potassium carbonate solution (19.5 mmol) and THF. . 225 mg of Pd(PPh3)4 (19.5 mmol) was added to the mixture 29 1374139 while the mixture was stirred and the mixture was refluxed for 6 hours. The mixture was cooled to room temperature, and then the obtained solid compound was filtered, washed with water, ethanol and THF to obtain 1.73 g of Compound 1 ' as a pale yellow powder (yield: 71%). (111\1411(4001^1^,00(:13)8.13-8.04(7H), 8.01(1H), 7.97-7.92(4H), 7.86-7.82 (2H), 7.75(2H), 7.71-7.58( 1〇Η), 7.32 (2H), 7·15 (1Η), 6.75 (1Η)). Synthesis Example 2: Synthesis of Compound 4 Compound 4 was synthesized via Reaction Scheme 2 below: Reaction Scheme 2

Synthesis of Compound 4 Intermediate 4d 5 g of imidazole was used. The pyridine compound Id (refer to Synthesis Example 1) (18 3 mmol) and 4.12 g of N-iodosuccinic acid (NIS) (18.3 mmol) were dissolved in acetonitrile as a solvent. The mixture was stirred at room temperature for 1 hour, and then 100 ml of gas was added to its 30 1374139. The mixture was rinsed with 1% aqueous sodium hydroxide solution and then rinsed with fresh aqueous sodium thiosulfate solution and water, and dried with X-free claws & 《, and then the resulting product 16 was removed and the solvent was removed. The resulting solid was washed with methanol and passed through to give a compound (yield: 79%). The obtained iodine compound and 1.76 g of phenylboric acid (14-5 mmol) were added to a mixed solvent of 1 g of an aqueous potassium carbonate solution and THF. To the mixture was added 335 mg of Pd(pph3)4 while the mixture was stirred, and the mixture was refluxed for 24 hours. The resulting product was extracted with dioxane. The water remaining in the organic layer is removed using water-free MgS 4 and dried under reduced pressure. The obtained product (ethyl acetate·n-hexane = 2:3) was purified by column chromatography to afford 2.93 g of intermediate 4d (yield 58%). Synthesis of Compound 4

Compound 4 was prepared in the same manner as Compound 1 according to Synthesis Example 1, except that Intermediate 4d was used instead of Intermediate 1d. 1 gram of intermediate lc (21.08 mmol) and 6.69 g of intermediate 4d (19-16 mmol) were subjected to ageing wood reaction' yielding 9.72 g of compound 4 in the form of a pale yellow powder (yield 73%) 〇 (lH NMR (400MHz, CDC13) 8.08 (1H), 8.03-8.01 (2H), 7.97-7.88 (3H), 7.81 (1H), 7.74-7.58 (12), 7.51-7.40(10), 7.29-7.23 ( 3H), 7.15 (1H), 6.69 (1H)). Synthesis Example 3: Synthesis of Compound 7 Compound 7 was synthesized via Reaction Scheme 3 below: 31 1374139

Reaction process 3

B(OH)2

Compound 7 was prepared in the same manner as in Synthesis Example 1, except that Intermediate 7d was used instead of Intermediate 1d. Substituting 1-aminoisoquinoline for 2-aminopyridine gave intermediate 7d. Make 10 grams of intermediate lc (21.08 milli

(S 32 1374139 Mo) and 6.19 g of the intermediate 7d (19.16 mmol) were subjected to a Suzuki reaction, yielding 9.03 g of the compound 7' in the form of a pale yellow powder (yield 7 %). (iH NMR (400MHz-CDC13) 8.69 (1H), 8.12 (2H), 8.07- 8.02 (5H), 7.99-7.95 (4H), 7.89-7.84 (2H), 7.79-7.75 (3H), 7.71-7· 65(4Η), 7.64-7·54(8Η), 7.33(2H), 7·02(1Η)). Synthesis Example 4: Synthesis of Compound 3 Compound 3 was synthesized via Reaction Scheme 4 below: Reaction Scheme 4

7.97- Compound 3 was prepared in the same manner as in Synthesis Example 1, except that Intermediate 3d was used instead of Intermediate id. The 2,4'-dibromopropyl benzene was substituted for 2,4'-dibromoacetanbenzene to obtain an intermediate 3d. 5 g of the intermediate lc (1 〇 54 mmol) and 2.75 g of the intermediate 3d (9.58 mmol) were subjected to a Suzuki reaction, yielding 4.15 g of the compound 3' in the form of a pale yellow powder (yield 68. / 〇) . (1H NMR (400MHz * CDC13) 8.12(2H), 8.07-8.02(5H), 33 1374139 7.95(2H), 7.89-7.84(2H), 7.80-7.71 (4H), 7.70- 7.66(3H), 7· 63-7·60(7Η), 7.32(2H), 7.15(1Η), 6.83(1H), 2.62(3H)) » Synthesis Example 5: Synthesis of Compound 2 Compound 2 was synthesized via Reaction Scheme 5 below. : Reaction Process 5

Compound 2 was prepared in the same manner as in Synthesis Example 1, except that Intermediate 2c was used instead of Intermediates 1b and 1c. Intermediate 2c was obtained using phenylmagnesium bromide instead of 2-naphthyl. 5 grams of intermediate 2c (13.36 house Moule) and 3.32 grams of intermediate ld (12.15 millimoles) were subjected to eucalyptus reaction,

4.64 g of compound 2' was produced in the form of a pale yellow powder (yield: 73%). (1H NMR (400MHz' CDC13) 8.11 (1H), 7.99 (2H), 7.95 (1H), 7.86 (1H), 7.64 (1H), 7.73-7.70 (2H), 7.69 (1H), 7.66-7.6 1 ( 7H), 7.58 (2H), 7.56-7, 50 (4H), 7.34 (2H), 7.17 (1H), 6.78 (1H)). Synthesis Example 6: Synthesis of Compound 1 1 Compound 1 1 was synthesized via Reaction Scheme 6 below: 34 1374139 Reaction Scheme 6

Compound 1 1 was prepared in the same manner as in Synthesis Examples 5 and 4, using Intermediates 2c and 3d. 5 grams of intermediate 2c (13.36 millimoles) and 3.49 grams of intermediate 3d (12.15 millimoles) were subjected to a reaction of eucalyptus to yield 4.72 grams of compound 11 in the form of a pale yellow powder (yield 72%). (1H NMR (400MHz, CDC13) 7.97 (1H), 7.91 (1H), 7.85 (2H), 7.80 (1H), 7.73-7.70 (2H), 7.69 (1H), 7.66-7.6 1 (7H), 7.58 ( 2H), 7·56-7·50 (4Η), 7_34(2H), 7.19(1H), 6.86(1H), 2.67(3H)). Example 1 A 15 ohm/cm 2 (1200 A) ITO glass substrate was cut into 50 mm χ 50 mm χ〇 7 mm size. Ultrasonic isopropyl alcohol rinse for $ minutes, then ultrasonically washed with pure water 5 minute. The substrate was then rinsed with UV ozone for 30 minutes. An inter-MTDATA vacuum coating was applied to the substrate to form a hole injection layer having a thickness of 750 Å. Then, a_NpD vacuum coating was formed on the hole injection layer to form a hole transport layer having a thickness of 15 Å. Using 97% by weight of the main body and 3 parts of the milk step as a dopant, a light-emitting layer having a thickness of 3 Å was formed on the electricity-transport layer. The compound 1 prepared by the synthesis was vacuum-coated on the light-emitting layer to form an electron having a thickness of 200 A outside the 35 13741. The LiF vacuum coating is formed on the electron transport layer to form an electron injecting layer having a thickness of 8 Å, and then the A1 vacuum film is placed on the electron injecting layer, and the cymbal and the cymbal are arbitrarily 3 〇〇〇A. The thickness of the cathode completes the organic light-emitting diode. Example 2 An organic light-emitting diode was fabricated as in Example i except that the compound 4 prepared in Synthesis Example 2 was used as the material of the electron transport layer. Example 3 An organic light-emitting diode was fabricated as in Example 1, except that the compound 7 prepared in Synthesis Example 3 was used as the material of the electron transport layer. Example 4 An organic light-emitting diode was fabricated as in Example 1, except that the compound 3 prepared in Synthesis Example 4 was used as the material of the electron transport layer. Example 5 An organic light-emitting diode was fabricated as in Example 1, except that it was used in synthesis.

The compound 5 prepared in Example 5 was used as a material of the electron transport layer. Example 6 An organic light-emitting diode was fabricated as in Example 1, except that the compound prepared in Synthesis Example 6 was used as a material for the electron transport layer. Comparative Example An organic light-emitting diode was fabricated in accordance with Example 1, except that Alq "8_Pyrene-based resin" was used as the material of the electron transport layer. Evaluation Example Using PR65〇 (Spectr〇scan) Source Measurement Unit · ( S) 36 1374139 (Ph〇t〇ReSearCh Ltd), measuring the current density (milliampere/cm 2 ), driving voltage (volt) of each organic light-emitting diode prepared according to Examples 1 to 3 and the comparative examples, Brightness (new candle/square meter) and efficiency ^ (4) / watt). The results are shown in Table i below and Figures 2 and 3. In particular, Figure 2 is an organic light-emitting diode of Comparative Example! And a graph of the voltage-current density characteristics of the organic light-emitting diode of the comparative example. Fig. 3 is a graph showing the luminance and efficiency characteristics of the organic light-emitting diode of Comparative Example 1 and 6 and the organic light-emitting diode of the comparative example. . Table 1

EXAMPLES Example 2 EXAMPLES Example 4 Example 5 Example 6 Material current density (milliamps per square centimeter) for forming an electron transport layer Compound 1 Compound 4 Compound 7 Compound 3 Compound 2 Driving voltage static 3 Λ 3.6 Brightness (new Candlelight / square meter) 780 774 Efficiency (light emphasis / watt) 7.25 6.67 5.1 4.0 3.7 996 6.06 1049 8.12 868 7.38 Compound 11 3.8 905 7.54

Comparative Embodiments As shown in Table 1 and Figures 2 and 3, the organic light-emitting diodes of Examples 6 to 6 have improved current mobility, driving voltage, and compared with the organic light-emitting diode of the comparative example. Brightness and efficiency. Therefore, an organic light-emitting diode having an organic layer containing a compound mainly composed of imidazopyridine represented by Formula 1 can be seen, which has a higher brightness than a conventional organic light-emitting diode.

Claims (1)

'Scope of application for patents: W^VZTTl Revision of the date of the month. Correction of the replacement page on December 1, 100. Formulation of the compound mainly composed of imidazopyridine represented by Formula 1. Han 4, R 'I one includes R6, R7, R8, R9, R丨. , R" and Ri2 Ri ' R2 ' R are respectively selected from the ruthenium atom R,, . . . to replace the halogen atom, the hydroxyl group, the cyano group, the sulphate, and the bio-substituted c ◦ An oxy group group, a substituted and unsubstituted substituted and unsubstituted and unsubstituted C, _C3 ° fluorenyl group, , a raw substituted and an unsubstituted one group: Diluted, group 'substituted and un(4) and substituted and unsubstituted::rc C6_C3 ° aryl group, group; generation C3_C3 芳 aryl group consisting of 5 R6 and r7 At least two rings forming a saturated or unsaturated ring; 9 10 R" at least two of aR12 form a saturated or unsaturated 1 and L2 ~ other it free single bond, substituted and unsubstituted Ci C stretch a group-based group, a substituted and unsubstituted CVC3. An extended aryl group consisting of a substituted and unsubstituted C3_c3 group of heterocyclic aryl groups and a group selected from the group consisting of substituted and Unsubstituted C6 group and substituted and unsubstituted c3_c3. Heteroaryl group 39 1374139 Revised December 2017 ^ Replacement page group; p and q Do not select from an integer from 1 to 5; and m and η are each selected from an integer from 〇 to 4, where „the two are not 0 at each time. 2. 2. For the compound of claim 1, wherein R| to Ri2 are respectively selected a free hydrogen atom, a substituted and unsubstituted alkyl group, a substituted and unsubstituted C2_C1() alkenyl group, a substituted and unsubstituted C6-Ci2 aryl group, and substituted and unsubstituted A group consisting of substituted C3_Ci2 heteroaryl groups. 3. The compound of claim 1, wherein R1 to R12 are each independently selected from the group consisting of a hydrogen atom, a C-C, a decyl group, a Ci_Ci〇 haloalkyl group, an alkenyl group, and a C2-C10 halogen. Alkenyl group, phenyl group, anthracenyl group, alkylphenyl group, Ci_Ci decyloxyphenyl group, naphthyl group, halophthyl group, alkylnaphthyl group and Ci_Ci〇 Alkoxynaphthyl group. 4. The compound of claim i, wherein at least two of & to & form a substituted or unsubstituted h a 2 aromatic ring. 5. If you apply for a patent scope! A compound of the formula wherein at least two of the & to the heart form a substituted or unsubstituted kb aromatic ring. 6. The compound of claim i, wherein ^ and ^ are selected from the group consisting of substituted and unsubstituted aryl groups and substituted and unsubstituted. a group consisting of 3_(:|2 heteroaryl groups. 7. The compound of claim 1 wherein the compound is selected from the group consisting of a phenylene group, a halogen group, and a Cl-ClQ group. Benzene It c-based extended base * soil and earth group 'extension of Qin group, tooth extension Cai Keji 1374139 December 1, 100 revised replacement group, C ^-Cw alkyl-naphthyl group and Ci_C| decane oxygen A group consisting of a group of naphthyl groups. 8. The compound of claim 1, wherein Ar| and Αι>2 are respectively selected from substituted and unsubstituted C6_Ci2 aryl groups and substituted and unsubstituted A group consisting of substituted Cs-C! 2 heteroaryl groups. 9. The compound of claim 2, wherein Ari and gossip are respectively selected from the group consisting of a phenyl group, a halophenyl group, a Cl_Ci decyl phenyl group, a Ci_Ci oxime oxyphenyl group, a naphthyl group. a group, a halonaphthyl group, a Cl-C10 alkylnaphthyl group, a C|-C10 alkoxynaphthyl group, an acridinyl group, a halopyridyl group, a CrCw alkyl pyridyl group, Cl a -c10 alkoxypyridyl group, a quinolyl group, a haloquinolyl group, a Cl_Cl〇 alkyl quinolyl group, a Cl_Ci oxime oxyquinolyl group, an isoquinolyl group a group consisting of a haloisoquinolyl group, a Cl_Ci fluorenyl isoquinolyl group, and a CrCw alkoxyisoquinolyl group. 10. A compound of claim 1 wherein m is hydrazine and η is 1 〇 11. The compound of claim 1 wherein both m and η are 1. 12. The imidazopyridine-based compound according to the first aspect of the patent application, wherein the imidazopyridine-based compound is selected from the group consisting of compounds represented by the formulae 1 a, 1 b, 1 c and 1 d: 1374139 December 1, 1 revision replacement page 42 1374139 December/Day 100 Correction Replacement Page Id 1 3 · A compound of the first application of the patent scope, wherein the amidine. The compound based on bite is selected from the group consisting of compounds 1 to 1 : Compound 1 Compound 2 43 1374139 Compound 5 December, December, revised replacement page 44 1374139 Compound 11 14. An organic light emitting diode (OLED), comprising: a first electrode; An organic layer between the first and second electrodes, the organic layer comprising a compound as in claim 1 of the patent application. 15. The organic light-emitting diode of claim 14, wherein the organic layer is an electron transport layer. 16. The organic light-emitting diode according to claim 15 further comprising a group selected from the group consisting of a hole injection layer, a hole transport layer, an electron barrier layer, a light-emitting layer, a hole barrier layer and an electron injection layer. The layers of the group. 45 1374139 December 2014 曰Correct replacement page 17. The organic light-emitting diode of claim 14 further includes a hole injection layer, a hole transport layer, a light-emitting layer and an electron injection layer, wherein the organic layer is Electronic transport layer. 18. The organic light-emitting diode according to claim 14 of the patent application, wherein the microphone. The bite-based compound is selected from the group consisting of compounds represented by the formulas la, lb, lc, and Id: Compound 1 a Compound 1 b Compound 1 c 46 December 100 Correct replacement page 1374139 Compound 1 d 19. The organic light-emitting diode according to claim 14, wherein the imidazopyridine-based compound is selected from the group consisting of Compounds 1 to 1 : Compound 1 Compound 2 47 1374139 % compound 6 48 1374139 December 1, 1 revised replacement page Compound 9 Compound 10 XI. Schema: as the next page 49