CN105745301A - Novel light emission compound and organic light emitting device comprising same - Google Patents
Novel light emission compound and organic light emitting device comprising same Download PDFInfo
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- CN105745301A CN105745301A CN201480063380.1A CN201480063380A CN105745301A CN 105745301 A CN105745301 A CN 105745301A CN 201480063380 A CN201480063380 A CN 201480063380A CN 105745301 A CN105745301 A CN 105745301A
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- 0 CC(C)(c1cccnc1-1)c2c-1*(C=CCC=C1)c1[n]2-c1cccc(*2CC=CCC2)n1 Chemical compound CC(C)(c1cccnc1-1)c2c-1*(C=CCC=C1)c1[n]2-c1cccc(*2CC=CCC2)n1 0.000 description 6
- HZYCXJRTTNAVQW-APZLZSJESA-N CC([n]1c(cccc2)c2c2c1CCC=C2)/N=C(\C=C(\c1ccccc1)/N)/[n](c(C1(C)C)c2-c3c1nccc3)c1c2ncnc1 Chemical compound CC([n]1c(cccc2)c2c2c1CCC=C2)/N=C(\C=C(\c1ccccc1)/N)/[n](c(C1(C)C)c2-c3c1nccc3)c1c2ncnc1 HZYCXJRTTNAVQW-APZLZSJESA-N 0.000 description 1
- BTUWVEDAYKPLGQ-UHFFFAOYSA-N CC1(C)C(N(C2C3N=CCC2)C(CC2)=CC(C4C=CC=CC44)=C2N4c2ccccc2)=C3C2=C1C=CCN2 Chemical compound CC1(C)C(N(C2C3N=CCC2)C(CC2)=CC(C4C=CC=CC44)=C2N4c2ccccc2)=C3C2=C1C=CCN2 BTUWVEDAYKPLGQ-UHFFFAOYSA-N 0.000 description 1
- MQNQJHOPFPIBLA-UHFFFAOYSA-N CC1(C)c([n](c2c3ccnc2)-c2cc4c(cccc5)c5c(c(C)ccc5)c5c4cc2)c3C2=C1CCC=N2 Chemical compound CC1(C)c([n](c2c3ccnc2)-c2cc4c(cccc5)c5c(c(C)ccc5)c5c4cc2)c3C2=C1CCC=N2 MQNQJHOPFPIBLA-UHFFFAOYSA-N 0.000 description 1
- OBMRSFKVIQKXPT-UHFFFAOYSA-N CC1(C)c(nccc2)c2-c(c2c3C=CC=CC2)c1[n]3-c1cc(-c2ccccc2)nc(C2=CC(C3)C3C=C2)n1 Chemical compound CC1(C)c(nccc2)c2-c(c2c3C=CC=CC2)c1[n]3-c1cc(-c2ccccc2)nc(C2=CC(C3)C3C=C2)n1 OBMRSFKVIQKXPT-UHFFFAOYSA-N 0.000 description 1
- NAHDYZXLVSIYJD-UHFFFAOYSA-N CCC([n]1c2ccccc2c2c1cccc2)/N=C(\NC(C)(C1=CC=CCC1)N)/[n](c(C1(C)C)c2C3=C1C=NC=CC3)c1c2ncnc1 Chemical compound CCC([n]1c2ccccc2c2c1cccc2)/N=C(\NC(C)(C1=CC=CCC1)N)/[n](c(C1(C)C)c2C3=C1C=NC=CC3)c1c2ncnc1 NAHDYZXLVSIYJD-UHFFFAOYSA-N 0.000 description 1
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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Abstract
An organic light emission compound of the present invention has excellent charge transport characteristics while having high triplet energy and Tg, thereby allowing an organic light emitting device to have a low driving voltage, high efficiency, low-consumption power, and a long lifespan when the organic light emission compound is applied to the organic light emitting device.
Description
Technical field
The present invention relates to novel light-emitting compound and the organic illuminating element comprising it.
Background technology
Recently, emissive type can the organic illuminating element of low voltage drive and the liquid crystal display (LCD of main flow as flat panel displaying element, liquidcrystaldisplay) compare, the excellence such as the angle of visual field, contrast, do not need backlight, it may be achieved light weight and slim, also favourable in power consumption, color reproduction range width, thus receiving publicity as display element of future generation.
The material being used as organic matter layer in organic illuminating element is broadly divided into luminescent material, hole-injecting material, hole mobile material, electron transport material, electron injection material etc. by function.Above-mentioned luminescent material can be divided into macromolecule and low molecule by molecular weight, can be divided into the fluorescent material of the singlet excited from electronics and the phosphor material of the triplet excited state from electronics by luminescence mechanism, luminescent material can be divided into blueness, green, red illuminating material and in order to present yellow needed for better natural colour and orange light emitting materials by glow color.Additionally, in order to increase increase by excitation and the luminous efficiency of energy transfer, it is possible to use main body/adulterant system is as luminescent substance.Its principle is as follows: if mixing a small amount of adulterant that band gap is little compared with the main body of main composition luminescent layer and luminous efficiency is excellent in luminescent layer, then the exciton transfer produced in main body sends the light that efficiency is high to adulterant.Now, the wavelength of main body moves to the wave band of adulterant, therefore according to the kind of the adulterant used and main body, can obtain the light of desired wavelength.
So far, as the material for such organic illuminating element, known multiple compounds, but when utilizing the organic illuminating element of in the past known material, in practical, there is many difficulties due to high driving voltage, poor efficiency and short life.Therefore, it is continually striving to utilize the material with excellent specific property to develop there is low voltage drive, high brightness and long-life organic illuminating element.
Summary of the invention
In order to solve problem as above, it is an object of the invention to, a kind of novel light-emitting compound is provided, this luminophor is due to charge transfer excellent and has high triplet energy and high Tg, thus can make it have low driving voltage, high efficiency, low power consumption, long-life when being applied to organic illuminating element.
The present invention also aims to, it is provided that be capable of low driving voltage, high efficiency, low power consumption, long-life organic illuminating element by comprising above-claimed cpd.
To achieve these goals, the present invention provides the luminophor represented by following chemical formula 1:
[chemical formula 1]
In above-mentioned formula,
X is each independently CR0Or N, R0For hydrogen；Deuterium；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Thiazolinyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Alkynyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkoxyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryloxy group；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryl；Or by deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Heteroaryl,
Y is C or Si,
R1For hydrogen；Deuterium；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Thiazolinyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Alkynyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkoxyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryloxy group；By deuterium, halogen, amino, itrile group, nitro, C1-30Alkyl, C2-30Thiazolinyl, C2-30Alkynyl, C1-30Alkoxyl, C6-30Aryloxy group, C6-30Aryl or C2-30The substituted or unsubstituted C of heteroaryl6-50Aryl；Or by deuterium, halogen, amino, itrile group, nitro, C1-30Alkyl, C2-30Thiazolinyl, C2-30Alkynyl, C1-30Alkoxyl, C6-30Aryloxy group, C6-30Aryl or C2-30The substituted or unsubstituted C of heteroaryl2-50Heteroaryl,
R2、R3、R4And R5It is each independently hydrogen；Deuterium；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Thiazolinyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Alkynyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkoxyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryloxy group；By deuterium, halogen, amino, itrile group, nitro, C1-30Alkyl, C2-30Thiazolinyl, C2-30Alkynyl, C1-30Alkoxyl, C6-30Aryloxy group, C6-30Aryl or C2-30The substituted or unsubstituted C of heteroaryl6-50Aryl；Or by deuterium, halogen, amino, itrile group, nitro, C1-30Alkyl, C2-30Thiazolinyl, C2-30Alkynyl, C1-30Alkoxyl, C6-30Aryloxy group, C6-30Aryl or C2-30The substituted or unsubstituted C of heteroaryl2-50Heteroaryl, R4And R5Can be selectively formed ring.
Additionally, the present invention provides comprises the organic illuminating element as luminescent substance of the compound represented by above-mentioned chemical formula 1 in organic matter layer.
The luminophor of the present invention is due to charge transfer excellent and has high triplet energy and high Tg, thus can make it have low driving voltage, high efficiency, low power consumption, long-life when being applied to organic illuminating element.
Accompanying drawing explanation
Fig. 1 schematically shows the cross section of OLED according to an embodiment of the invention.
Reference numeral
10: substrate
11: anode
12: hole injection layer
13: hole transmission layer
14: luminescent layer
15: electron transfer layer
16: negative electrode
Detailed description of the invention
The compound of the present invention is characterised by being represented by following chemical formula 1.
[chemical formula 1]
In above-mentioned formula,
X is each independently CR0Or N, R0For hydrogen；Deuterium；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Thiazolinyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Alkynyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkoxyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryloxy group；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryl；Or by deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Heteroaryl,
Y is C or Si,
R1For hydrogen；Deuterium；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Thiazolinyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Alkynyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkoxyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryloxy group；By deuterium, halogen, amino, itrile group, nitro, C1-30Alkyl, C2-30Thiazolinyl, C2-30Alkynyl, C1-30Alkoxyl, C6-30Aryloxy group, C6-30Aryl or C2-30The substituted or unsubstituted C of heteroaryl6-50Aryl；Or by deuterium, halogen, amino, itrile group, nitro, C1-30Alkyl, C2-30Thiazolinyl, C2-30Alkynyl, C1-30Alkoxyl, C6-30Aryloxy group, C6-30Aryl or C2-30The substituted or unsubstituted C of heteroaryl2-50Heteroaryl,
R2、R3、R4And R5It is each independently hydrogen；Deuterium；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Thiazolinyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Alkynyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkoxyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryloxy group；By deuterium, halogen, amino, itrile group, nitro, C1-30Alkyl, C2-30Thiazolinyl, C2-30Alkynyl, C1-30Alkoxyl, C6-30Aryloxy group, C6-30Aryl or C2-30The substituted or unsubstituted C of heteroaryl6-50Aryl；Or by deuterium, halogen, amino, itrile group, nitro, C1-30Alkyl, C2-30Thiazolinyl, C2-30Alkynyl, C1-30Alkoxyl, C6-30Aryloxy group, C6-30Aryl or C2-30The substituted or unsubstituted C of heteroaryl2-50Heteroaryl, R4And R5Can be selectively formed ring.
In the present invention, the compound represented by above-mentioned chemical formula 1 is that the one in following structure is preferred.
In said structure, X, R4And R5Identical with the definition in chemical formula 1.
Z is CR8Or N, R8For hydrogen；Deuterium；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Thiazolinyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Alkynyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkoxyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryloxy group；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryl；Or by deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Heteroaryl,
A is O, S, Se, TE, N-Ar1, wherein, Ar1For hydrogen；Deuterium；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Thiazolinyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Alkynyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkoxyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryloxy group；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryl；Or by deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Heteroaryl,
Ar is each independently by deuterium, halogen, amino, itrile group, nitro, C1-30Alkyl, C2-30Thiazolinyl, C2-30Alkynyl, C1-30Alkoxyl, C6-30Aryloxy group, C6-30Aryl or C2-30The substituted or unsubstituted C of heteroaryl6-38Aryl；Or by deuterium, halogen, amino, itrile group, nitro, C1-30Alkyl, C2-30Thiazolinyl, C2-30Alkynyl, C1-30Alkoxyl, C6-30Aryloxy group, C6-30Aryl or C2-30The substituted or unsubstituted C of heteroaryl2-38Heteroaryl,
R6And R7It is each independently hydrogen；Deuterium；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Thiazolinyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Alkynyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkoxyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryloxy group；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryl；Or by deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Heteroaryl,
N is the integer of 2 to 6.
In the present invention, the preference of the compound represented by above-mentioned chemical formula 1 is as follows:
The compound of the chemical formula 1 according to the present invention is due to charge transfer excellent and has high triplet energy and high Tg, thus can make it have low driving voltage, high efficiency, low power consumption, long-life when being applied to organic illuminating element.
Additionally, the present invention provides the manufacture method of chemical formula 1, it is characterised in that include the step of following reaction equation 1:
[reaction equation 1]
The concrete example of above-mentioned reaction equation 1 can be following reaction equation 1-1.
[reaction equation 1-1]
In above-mentioned reaction equation, X, Y, Ar, R1、R2、R3、R4And R5Identical with above-mentioned definition respectively.
Additionally, the present invention provides comprises the organic illuminating element as luminescent substance of the compound represented by above-mentioned chemical formula 1 in organic matter layer.Now, the compound of the present invention can be used alone or uses together with known organic luminescent compounds.
Additionally, the organic illuminating element of the present invention comprises the organic matter layer of more than 1 layer containing the compound represented by above-mentioned chemical formula 1, the manufacture method of above-mentioned organic illuminating element as described below.
Above-mentioned organic illuminating element can comprise the organic matter layers more than one layer such as hole injection layer (HIL), hole transmission layer (HTL), luminescent layer (EML), electron transfer layer (ETL), electron injecting layer (EIL) between anode (anode) and negative electrode (cathode).
First, there is the anode electrode material of high work function at substrate top evaporation and form anode.Now, aforesaid substrate can use the substrate used in common organic illuminating element, and the glass substrate excellent especially with mechanical strength, heat stability, the transparency, surface smoothness, handling easiness and water proofing property or transparent plastic substrate are preferred.Additionally, as anode electrode material, it is possible to use the tin indium oxide (ITO) of transparent and electrically conductive excellence, indium zinc oxide (IZO), stannum oxide (SnO2), zinc oxide (ZnO) etc..Above-mentioned anode electrode material can be deposited with by common anodic formation method, specifically can be deposited with by vapour deposition method or sputtering method.
Secondly, vacuum vapour deposition, spin-coating method, casting, LB (Langmuir-Blodgett can be passed through, Lang Gemiaoer Blodget) method such as method, hole injection layer material is formed on above-mentioned anode electrode top, but from being readily available uniform film quality and being not likely to produce pin holeDeng aspect consider, it is preferable that formed by vacuum vapour deposition.When forming hole injection layer by above-mentioned vacuum vapour deposition, although its evaporation condition is different according to the compound of the material as hole injection layer, the structure of target hole injection layer and thermal characteristics etc., but generally preferable evaporation temperature at 50-500 DEG C, 10-8To 10-3Holder the vacuum of (torr), 0.01 toEvaporation rate,Suitably select to the Layer thickness of 5 μm.
Above-mentioned hole injection layer material is not particularly limited, it is possible to use phthalocyanine compound or the star-like amine such as CuPc disclosed in U.S. Patent No. 4,356,429Derivatives class and TCTA (4,4', 4 "-three (N-carbazyl) triphenylamine), m-MTDATA (4; 4'; 4 "-three (3-MethYlphenylamino) triphenylamine), m-MTDAPB (4,4', 4 "-three (3-MethYlphenylamino) phenoxy group benzene), HI-406 (N1,N1'-(biphenyl-4,4'-two base) double; two (N1-(naphthalene-1-base)-N4,N4-diphenyl benzene-1,4-diamidogen) etc. as hole injection layer material.
Secondly, the methods such as vacuum vapour deposition, spin-coating method, casting, LB method can be passed through, hole transmission layer material is formed on above-mentioned hole injection layer top, but from the viewpoint of being readily available uniform film quality and being not likely to produce pin hole etc., it is preferable that formed by vacuum vapour deposition.When forming hole transmission layer by above-mentioned vacuum vapour deposition, although its evaporation condition is different according to the compound used, but generally select to be preferred in the condition and range almost identical with the formation of hole injection layer.
Additionally, above-mentioned hole transmission layer material is not particularly limited, it is possible to the common known material used from hole transmission layer arbitrarily selects use.Specifically, above-mentioned hole transmission layer material can use the carbazole derivates such as N-phenyl carbazole, polyvinylcarbazole, N, double; two (3-the aminomethyl phenyl)-N of N'-, N'-diphenyl-[1,1-xenyl]-4,4'-diamidogen (TPD), N, N'-bis-(naphthalene-1-base)-N, N'-diphenylbenzidine (α-NPD) etc. has the common amine derivative etc. of aromatic fused ring.
Afterwards, the methods such as vacuum vapour deposition, spin-coating method, casting, LB method can be passed through, luminescent layer material is formed on above-mentioned hole transmission layer top, but from the viewpoint of being readily available uniform film quality and being not likely to produce pin hole etc., it is preferable that formed by vacuum vapour deposition.When forming luminescent layer by above-mentioned vacuum vapour deposition, although its evaporation condition is different according to the compound used, but generally select to be preferred in the condition and range almost identical with the formation of hole injection layer.Additionally, above-mentioned emitting layer material can use the compound represented by chemical formula 1 of the present invention as main body or adulterant.
When using the compound represented by above-mentioned chemical formula 1 as light emitting host, it is possible to phosphorescence or fluorescent dopants are used together and forms luminescent layer.Now, as fluorescent dopants, it is possible to use from IDE102, IDE105 or BD142 (N that Chu Guangxingchan company (Idemitsu company) can buy6,N12-bis-(3,4-3,5-dimethylphenyl)-N6,N12-twoBase-6,12-diamidogen), as phosphorescent dopants, it is possible to common vacuum evaporation (doping) has green phosphorescent adulterant Ir (ppy)3(three (2-phenylpyridines) close iridium), F2Irpic (double; two [4 as blue phosphorescent adulterant, 6-difluorophenyl pyridinato-N, C2 '] pyridinecarboxylic conjunction iridium (III), iridiumIIIbis [4,6-di-fluorophenyl-pyridinato-N, C2 '] picolinate), the red phosphorescent adulterant RD61 etc. of UDC company.The doping content of adulterant is not particularly limited, but relative to main body 100 weight portion, it is preferable that with 0.01 to 15 weight portion doped with adulterant.If the content of adulterant is less than 0.01 weight portion, then there is the problem that cannot smoothly complete that develops the color because dopant dose is insufficient, when more than 15 weight portion, there is the problem of efficiency dramatic drop-off because of concentration quenching phenomena.
Additionally, in luminescent layer and when using phosphorescent dopants, in order to prevent triplet exciton or hole to be diffused into the phenomenon of electron transfer layer, it is preferable that by vacuum vapour deposition or spin-coating method, further stacking hole barrier materials (HBL).Now spendable hole barrier material is not particularly limited, it is possible to select any one to use from as the known material of hole barrier materials.Such as can enumerateHole barrier materials etc. described in oxadiazole derivative, triazole derivative, phenanthroline derivative or Japanese Unexamined Patent Publication 11-329734 (A1), Balq (double; two (8-hydroxy-2-methylquinoline)-xenol aluminum), phenanthroline (phenanthrolines) based compound can be used typically (such as, the BCP (Bathocuproine, bathocuproine) of UDC company) etc..
On luminescent layer top as formed above, forming electron transfer layer, now, above-mentioned electron transfer layer is formed by methods such as vacuum vapour deposition, spin-coating method, castings, it is particularly preferred to formed by vacuum vapour deposition.
Above-mentioned electron transport layer materials plays the effect stably will transmitted from electron injection electrode injected electrons, and its kind is not particularly limited, for instance can use quinoline, particularly three (oxine) aluminum (Alq3) or ET4 (6,6'-(3,4-bis-Base-1,1-dimethyl-1H-thiophene coughs up-2,5-two base) two-2,2'-bipyridyl (6,6'-(3,4--1,1--1H--2,5- )-2,2'-)).Additionally, portion on the electron transport layer, it is possible to stacking has the material of the effect easily making electronics inject, i.e. electron injecting layer (EIL) from negative electrode, as electron injecting layer material, it is possible to use LiF, NaCl, CsF, Li2The materials such as O, BaO.
Additionally, the evaporation condition of above-mentioned electron transfer layer is different according to the compound used, but generally select to be preferred in the condition and range almost identical with the formation of hole injection layer.
Afterwards, on above-mentioned electron transfer layer top, it is possible to form electron injecting layer material, now, about above-mentioned electron transfer layer, it is possible to form common electron injecting layer material by methods such as vacuum vapour deposition, spin-coating method, castings, it is particularly preferred to formed by vacuum vapour deposition.
Finally, by the method such as vacuum vapour deposition or sputtering method, form negative electrode formation metal on electron injecting layer top, thus being used as negative electrode.At this, as negative electrode formation metal, it is possible to use have the metal of low work function, alloy, conductive compound and their mixture.As concrete example, there are lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-Yin (Mg-Ag) etc..Additionally, in order to obtain top light emitting elementThe transmission-type negative electrode using ITO, IZO can also be adopted.
The organic illuminating element of the present invention can not only realize the organic illuminating element of anode, hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer, cathode construction, and it is capable of the structure of the organic illuminating element of various structures, it is also possible to form the intermediate layer of a layer or two-layer as required further.
As it has been described above, the thickness of each organic matter layer formed according to the present invention can regulate according to required degree, it is preferred to 10 to 1000nm, more preferably 20 to 150nm.
Additionally, the organic matter layer comprising compound represented by above-mentioned chemical formula 1 of the present invention owing to can regulate the thickness of organic matter layer with molecular unit, therefore there is the advantage that surface is uniform, morphological stability is excellent.
The organic illuminating element of the present invention is owing to comprising charge transfer excellent and having the compound that the chemical formula 1 of high triplet energy and high Tg represents such that it is able to show low driving voltage, high efficiency, low power consumption, long-life.
Hereinafter, in order to contribute to understanding the present invention, open preferred embodiment, but following embodiment only illustrates the present invention, and the scope of the present invention is not limited to following embodiment.
The synthesis of intermediate A
[synthesis of A-1]
In round-bottomed flask, (1H-indol-3-yl) boric acid 41.17g, 2-methyl-bromobenzoate 50g is dissolved in toluene 600ml, adds the K of 350ml2CO3(2M) with the Pd (PPh of 8.1g3)4, then carry out return stirring.Confirm reaction by TLC, and add water, then terminate reaction.Being extracted and after filtration under diminished pressure with EA by organic layer, upper prop is refined, and obtains the intermediate A-1 (yield 72%) of 42.1g.
[synthesis of A-2]
The above-mentioned A-1 of 42g is dissolved in the THF of 1000ml, then temperature is reduced to 0 DEG C.It is slowly added the CH of 167ml3MgBr, and be raised slowly to room temperature and stir 1 hour, then carry out return stirring.Being extracted and after filtration under diminished pressure with MC by organic layer, upper prop is refined, and obtains the intermediate A-2 (yield 68%) of 28.6g.
[synthesis of A]
In the above-mentioned A-2 of 28g, after adding acetic acid 280ml and hydrochloric acid 1.0ml, carry out return stirring 24 hours, then temperature is reduced to room temperature.After being filtered by the solid precipitated out, upper prop is refined, and obtains the intermediate A (yield 60%) of 15.3g.
The synthesis of intermediate B
[synthesis of B-1]
In round-bottomed flask, (1H-indol-3-yl) boric acid 24.7g, 2-methyl-bromobenzoate 30g is dissolved in toluene 350ml, adds the K of 210ml2CO3(2M) with the Pd (PPh of 4.84g3)4, then carry out return stirring.Confirm reaction by TLC, and add water, then terminate reaction.Being extracted and after filtration under diminished pressure with EA by organic layer, upper prop is refined, and obtains the intermediate B-1 (yield 72%) of 25.2g.
[synthesis of B-2]
The above-mentioned B-1 of 42g is dissolved in the THF of 600ml, then temperature is reduced to 0 DEG C.It is slowly added the PhMgBr of 99ml, and is raised slowly to room temperature and stirs 1 hour, then carry out return stirring.Being extracted and after filtration under diminished pressure with MC by organic layer, upper prop is refined, and obtains the intermediate B-2 (yield 71%) of 26.5g.
[synthesis of B]
In the above-mentioned B-2 of 26g, after adding acetic acid 260ml and hydrochloric acid 1.0ml, carry out return stirring 24 hours, then temperature is reduced to room temperature.After being filtered by the solid precipitated out, upper prop is refined, and obtains the intermediate B (yield 67%) of 16.6g.
Embodiment 1: the synthesis of compound 1
Pd by bromo-for the 4-of the above-mentioned intermediate A of 2.5g, 3.99g 2,6-diphenyl pyridine, t-BuONa, 0.40g of 1.54g2(dba)3, 0.5ml (t-Bu)3P is dissolved in toluene 40ml, then carries out return stirring.After confirming reaction terminating by TLC, being extracted and after filtration under diminished pressure with MC by organic layer, upper prop is refined, and obtains the compound 1 (yield 52%) of 2.58g.
M/z:462.21 (100.0%), 463.21 (37.5%), 464.22 (6.7%)
Embodiment 2: the synthesis of compound 2
Replace bromo-2, the 6-diphenyl pyridines of 4-to react with bromo-4, the 6-diphenyl pyridines of 2-, in addition, synthesize compound 2 by the method identical with compound 1.
M/z:462.21 (100.0%), 463.21 (37.5%), 464.22 (6.7%)
Embodiment 3: the synthesis of compound 3
Replace bromo-2, the 6-diphenyl pyridines of 4-to react with bromo-2, the 6-diphenylpyrimidin of 4-, in addition, synthesize compound 3 by the method identical with compound 1.
M/z:463.20 (100.0%), 464.21 (36.0%), 465.21 (6.7%), 464.20 (1.1%)
Embodiment 4: the synthesis of compound 4
Replace bromo-2, the 6-diphenyl pyridines of 4-to react with bromo-4, the 6-diphenylpyrimidin of 2-, in addition, synthesize compound 4 by the method identical with compound 1.
M/z:463.20 (100.0%), 464.21 (36.0%), 465.21 (6.7%), 464.20 (1.1%)
Embodiment 5: the synthesis of compound 5
The NaH of the above-mentioned intermediate A of 2.5g, 0.31g is put into the DMF of 25ml and stirs.It is slowly added dropwise the solution after the DMF that chloro-for 2-4,6-diphenyl-1,3,5-triazine 3.44g is dissolved in 35ml wherein.After stirring at normal temperature, confirm reaction terminating by TLC, carry out silica filtration, then recrystallization, obtain the compound 5 (yield 49%) of 2.44g.
M/z:464.20 (100.0%), 465.20 (36.1%), 466.21 (5.9%)
Embodiment 6: the synthesis of compound 6
Replace bromo-2, the 6-diphenyl pyridines of 4-to react with 4-(3-bromophenyl)-2,6-diphenylpyrimidin, in addition, synthesize compound 6 by the method identical with compound 1.
M/z:539.24 (100.0%), 540.24 (42.5%), 541.24 (9.1%), 542.25 (1.2%), 540.23 (1.1%)
Embodiment 7: the synthesis of compound 7
Replace bromo-2, the 6-diphenyl pyridines of 4-to react with 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazines, in addition, synthesize compound 7 by the method identical with compound 1.
M/z:540.23 (100.0%), 541.23 (42.6%), 542.24 (8.4%), 543.24 (1.2%)
Embodiment 8: the synthesis of compound 8
Replace above-mentioned intermediate A by intermediate B, replace bromo-2, the 6-diphenyl pyridines of 4-to react with bromo-4, the 6-diphenyl pyridines of 2-, in addition, synthesize compound 8 by the method identical with compound 1.
M/z:587.24 (100.0%), 588.24 (46.8%), 589.24 (11.1%), 590.25 (1.6%), 588.23 (1.1%)
Embodiment 9: the synthesis of compound 9
Replace above-mentioned intermediate A to react by intermediate B, in addition, synthesize compound 9 by the method identical with compound 5.
M/z:588.23 (100.0%), 589.23 (46.9%), 590.24 (10.2%), 591.24 (1.6%)
Embodiment 10: the synthesis of compound 10
Replace above-mentioned intermediate A by intermediate B, replace bromo-2, the 6-diphenyl pyridines of 4-to react with 4-(3-bromophenyl)-2,6-diphenylpyrimidin, in addition, synthesize compound 10 by the method identical with compound 1.
M/z:663.27 (100.0%), 664.27 (53.4%), 665.27 (14.3%), 666.28 (2.4%), 664.26 (1.1%)
Embodiment 11: the synthesis of compound 11
Replace above-mentioned intermediate A by intermediate B, replace bromo-2, the 6-diphenyl pyridines of 4-to react with 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazines, in addition, synthesize compound 11 by the method identical with compound 1.
M/z:664.26 (100.0%), 665.27 (52.3%), 666.27 (13.4%), 667.27 (2.4%), 665.26 (1.5%)
Embodiment 12: the synthesis of compound 12
Replace bromo-2, the 6-diphenyl pyridines of 4-to react with 9-(3-bromophenyl)-9H-carbazole, in addition, synthesize compound 12 by the method identical with compound 1.
M/z:474.21 (100.0%), 475.21 (38.6%), 476.22 (7.1%)
Embodiment 13: the synthesis of compound 13
Replace bromo-2, the 6-diphenyl pyridines of 4-to react with 3-bromo-9-phenyl-9H-carbazole, in addition, synthesize compound 13 by the method identical with compound 1.
M/z:474.21 (100.0%), 475.21 (38.6%), 476.22 (7.1%)
The manufacture of organic illuminating element
According to structure described in Fig. 1, manufacture organic illuminating element.About organic illuminating element, stack gradually anode from down(hole injecting electrode 11)/hole injection layer 12/ hole transmission layer 13/ luminescent layer 14/ electron transfer layer 15/ negative electrode(electron injection electrode 16).
The hole injection layer 12 of embodiment and comparative example, hole transmission layer 13, luminescent layer 14, electron transfer layer 15 employ following material.
Embodiment 14
Will be withThickness thin film is coated with the glass substrate distilled water of tin indium oxide (ITO), ultrasonic waves for cleaning.Distilled water cleans after terminating, carry out ultrasonic waves for cleaning with isopropanol, acetone, methanol equal solvent and dry, then after being transferred to plasma cleaner, utilize oxygen plasma, after aforesaid substrate is cleaned 5 minutes, utilizing thermal vacuum coater (thermalevaporator), portion manufactures hole injection layer HT01 on an ito substrateNPB as hole transmission layerFilm.Then, as luminescent layer, with 10% doping Ir (ppy) in above-claimed cpd 13, manufactureFilm.Then, as electron transfer layer, manufacture with ET01:Liq (1:1)Film after, manufacture LiFFilm, aluminum (Al)Film, this element is sealed (Encapsulation) in glove box, thus making green organic illuminating element.
Embodiment 15 to embodiment 26
By the method identical with embodiment 1, make the green organic illuminating element using compound 2 to 11 to replace compound 1 to be filmed respectively as luminescent layer main body.
Comparative example 1
Use CBP to replace the compound 1 in the luminescent layer main body of above-described embodiment 1, in addition, make green organic illuminating element by identical method.
Comparative example 2
Use comparative compound 1 to replace the compound 1 in the luminescent layer main body of above-described embodiment 1, in addition, make green organic illuminating element by identical method.
The performance evaluation of organic illuminating element
Voltage is applied by Keithley 2400 digital sourcemeter (Kiethley2400sourcemeasurementunit), inject electronics and hole, utilize Konica Minolta (KonicaMinolta) spectroradiometer (CS-2000), measure brightness when sending light, thus measuring for executing alive electric current density and brightness under atmospheric conditions, the performance of the organic illuminating element of Evaluation operation example and comparative example, the results are shown in table 1.
Table 1
[table 1]
Can confirm that as shown in Table 1 above, embodiments of the invention are compared with comparative example 1 to 2, and the physical property of organic illuminating element goes up all excellent in all respects.
Industrial applicability
The luminophor of the present invention is due to charge transfer excellent and has high triplet energy and high Tg, thus can make it have low driving voltage, high efficiency, low power consumption, long-life when being applied to organic illuminating element.
Claims (6)
1. the luminophor represented by a following chemical formula 1:
Chemical formula 1
In above-mentioned formula,
X is each independently CR0Or N, R0For hydrogen；Deuterium；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Thiazolinyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Alkynyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkoxyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryloxy group；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryl；Or by deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Heteroaryl,
Y is C or Si,
R1For hydrogen；Deuterium；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Thiazolinyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Alkynyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkoxyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryloxy group；By deuterium, halogen, amino, itrile group, nitro, C1-30Alkyl, C2-30Thiazolinyl, C2-30Alkynyl, C1-30Alkoxyl, C6-30Aryloxy group, C6-36Aryl or C2-36The substituted or unsubstituted C of heteroaryl6-50Aryl；Or by deuterium, halogen, amino, itrile group, nitro, C1-30Alkyl, C2-30Thiazolinyl, C2-30Alkynyl, C1-30Alkoxyl, C6-30Aryloxy group, C6-36Aryl or C2-36The substituted or unsubstituted C of heteroaryl2-50Heteroaryl,
R2、R3、R4And R5It is each independently hydrogen；Deuterium；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Thiazolinyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Alkynyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkoxyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryloxy group；By deuterium, halogen, amino, itrile group, nitro, C1-30Alkyl, C2-30Thiazolinyl, C2-30Alkynyl, C1-30Alkoxyl, C6-30Aryloxy group, C6-30Aryl or C2-30The substituted or unsubstituted C of heteroaryl6-50Aryl；Or by deuterium, halogen, amino, itrile group, nitro, C1-30Alkyl, C2-30Thiazolinyl, C2-30Alkynyl, C1-30Alkoxyl, C6-30Aryloxy group, C6-30Aryl or C2-30The substituted or unsubstituted C of heteroaryl2-50Heteroaryl, R4And R5Can be selectively formed ring.
2. luminophor according to claim 1, it is characterised in that represented by any one in following structure:
In said structure, X, R4And R5It is identical with the definition in chemical formula 1,
Z is CR8Or N, R8For hydrogen；Deuterium；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Thiazolinyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Alkynyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkoxyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryloxy group；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryl；Or by deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Heteroaryl,
A is O, S, Se, TE, N-Ar1, wherein, Ar1For hydrogen；Deuterium；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Thiazolinyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Alkynyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkoxyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryloxy group；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryl；Or by deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Heteroaryl,
Ar is each independently by deuterium, halogen, amino, itrile group, nitro, C1-30Alkyl, C2-30Thiazolinyl, C2-30Alkynyl, C1-30Alkoxyl, C6-30Aryloxy group, C6-30Aryl or C2-30The substituted or unsubstituted C of heteroaryl6-38Aryl；Or by deuterium, halogen, amino, itrile group, nitro, C1-30Alkyl, C2-30Thiazolinyl, C2-30Alkynyl, C1-30Alkoxyl, C6-30Aryloxy group, C6-30Aryl or C2-30The substituted or unsubstituted C of heteroaryl2-38Heteroaryl,
R6And R7It is each independently hydrogen；Deuterium；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Thiazolinyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Alkynyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkoxyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryloxy group；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryl；Or by deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Heteroaryl,
N is the integer of 2 to 6.
3. luminophor according to claim 1, it is characterised in that represented by any one in following chemical formula:
4. the manufacture method of a chemical formula 1, it is characterised in that include represented by following reaction equation 1 step:
Reaction equation 1
In above-mentioned reaction equation, X, R1、R2、R3、R4And R5Identical with the definition in chemical formula 1 respectively.
5. an organic illuminating element, it comprises the organic matter layer of anode, negative electrode and between two electrodes more than one layer containing compound described in claim 1.
6. organic illuminating element according to claim 5, it is characterised in that described organic matter layer contains the compound described in claim 1 as light emitting host or adulterant.
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| KR20200099833A (en) | 2019-02-15 | 2020-08-25 | 삼성전자주식회사 | Condensed cyclic compound and organic light emitting device comprising the same |
| KR102134380B1 (en) * | 2019-04-03 | 2020-07-16 | 주식회사 엘지화학 | Novel hetero-cyclic compound and organic light emitting device comprising the same |
| KR20200117249A (en) | 2019-04-03 | 2020-10-14 | 삼성전자주식회사 | Condensed cyclic compound and organic light emitting device comprising the same |
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| JP2006219393A (en) * | 2005-02-09 | 2006-08-24 | Canon Inc | Compound, light emitting device and image display device |
| JP2010040829A (en) * | 2008-08-06 | 2010-02-18 | Konica Minolta Holdings Inc | Organic electroluminescent element, display device, and lighting system |
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| CN1049156A (en) * | 1989-06-22 | 1991-02-13 | 巴斯大学 | Indenoindole compounds |
| JP2006219393A (en) * | 2005-02-09 | 2006-08-24 | Canon Inc | Compound, light emitting device and image display device |
| JP2010040829A (en) * | 2008-08-06 | 2010-02-18 | Konica Minolta Holdings Inc | Organic electroluminescent element, display device, and lighting system |
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| CN113831275A (en) * | 2021-09-01 | 2021-12-24 | 上海兆维科技发展有限公司 | Indole-substituted 6-phenylindenoindole derivative and preparation method and application thereof |
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