TWI651318B - An organic electroluminescent device comprising a bipolar host material of a spiro [fluorene-9,2'-imidazole] group - Google Patents
An organic electroluminescent device comprising a bipolar host material of a spiro [fluorene-9,2'-imidazole] group Download PDFInfo
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- TWI651318B TWI651318B TW106138222A TW106138222A TWI651318B TW I651318 B TWI651318 B TW I651318B TW 106138222 A TW106138222 A TW 106138222A TW 106138222 A TW106138222 A TW 106138222A TW I651318 B TWI651318 B TW I651318B
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- 239000000463 material Substances 0.000 title claims abstract description 32
- HFNOABKYQHZEPJ-UHFFFAOYSA-N spiro[fluorene-9,2'-imidazole] Chemical group N=1C2(N=CC=1)C1=CC=CC=C1C=1C=CC=CC=12 HFNOABKYQHZEPJ-UHFFFAOYSA-N 0.000 title 1
- 239000010410 layer Substances 0.000 claims abstract description 40
- 239000012044 organic layer Substances 0.000 claims abstract description 16
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims abstract description 13
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims abstract description 9
- -1 diphenylamino Chemical group 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 230000000903 blocking effect Effects 0.000 claims abstract description 7
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 229950000688 phenothiazine Drugs 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 3
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 7
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 238000004528 spin coating Methods 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000010409 thin film Substances 0.000 claims 1
- 238000002347 injection Methods 0.000 abstract description 11
- 239000007924 injection Substances 0.000 abstract description 11
- 230000009477 glass transition Effects 0.000 abstract description 9
- 230000005540 biological transmission Effects 0.000 abstract description 4
- 238000002474 experimental method Methods 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 10
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229940125782 compound 2 Drugs 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
- 239000005695 Ammonium acetate Substances 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 235000019257 ammonium acetate Nutrition 0.000 description 3
- 229940043376 ammonium acetate Drugs 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- 238000003477 Sonogashira cross-coupling reaction Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000010405 reoxidation reaction Methods 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- MTCARZDHUIEYMB-UHFFFAOYSA-N 2-bromofluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Br)=CC=C3C2=C1 MTCARZDHUIEYMB-UHFFFAOYSA-N 0.000 description 1
- JSEQNGYLWKBMJI-UHFFFAOYSA-N 9,9-dimethyl-10h-acridine Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3NC2=C1 JSEQNGYLWKBMJI-UHFFFAOYSA-N 0.000 description 1
- 238000007125 Buchwald synthesis reaction Methods 0.000 description 1
- 241000237858 Gastropoda Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- DZBUGLKDJFMEHC-UHFFFAOYSA-N benzoquinolinylidene Natural products C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001808 coupling effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 150000008376 fluorenones Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Organic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
本發明涉及有機電致發光器件,包括陰極、陽極和有機層,所述有機 層為空穴阻擋層、電子傳輸層、發光層中的一層或多層,所述有機層具有式(I)所述結構的化合物,其中,R1-R3為示為C1-C4烷基或烷氧基取代或未取代的吖啶基、吩噻嗪基、咔唑基、二苯胺基,氫,鹵素,C1-C4烷基。實驗表明,本發明的器件由於採用的雙極材料具有較高的玻璃化轉變溫度(Tg=158℃),雙極材料有利於載流子注入和傳輸平衡,因此發光效率高,使用壽命長。 The present invention relates to an organic electroluminescent device comprising a cathode, an anode and an organic layer, the organic layer being a hole blocking layer, an electron transporting layer, one or more layers in the light emitting layer, the organic layer having the formula (I) A compound of the formula wherein R 1 -R 3 are a C1-C4 alkyl or alkoxy substituted or unsubstituted acridinyl, phenothiazine, carbazolyl, diphenylamino, hydrogen, halogen, C1 -C4 alkyl. Experiments show that the device of the present invention has a high glass transition temperature (T g = 158 ° C) due to the bipolar material used, and the bipolar material is advantageous for carrier injection and transmission balance, thereby high luminous efficiency and long service life. .
Description
本發明涉及有機電致發光器件,具體涉及一種以螺[芴-9,2’-咪唑]為中心核的雙極主體材料製備的有機電致發光器件。 The present invention relates to an organic electroluminescent device, and in particular to an organic electroluminescent device prepared from a bipolar host material having a snail [芴-9, 2'-imidazole] as a central core.
有機發光二極體(OLED)具有相應速度快、耗能低、亮度高、視角廣、可彎曲、主動發光等特性,受到了科學界和產業界的高度重視。其在顯示、照明等方面的應用具有較大的潛力。電致螢光和電致磷光分別被稱為第一代和第二代OLED。基於螢光材料的OLED具有穩定性高的特點,但受限於量子統計學定律,在電啟動作用下,產生的單線態激子和三線態激子的比例為1:3,所以螢光材料電致發光內量子效率最大僅有25%。而磷光材料具有重原子的自旋軌道耦合作用,可以綜合利用單線態激子和三線態激子,理論的內量子效率可達100%,但是基於磷光的OLED具有明顯的效率滾降效應,在高亮度應用中有一定的阻礙。另外,磷光材料需用使用Pt,Ir等貴價金屬,因此磷光材料價格較高。而目前,OLED器件中客體材料主要應用磷光材料。 The organic light-emitting diode (OLED) has the characteristics of high speed, low energy consumption, high brightness, wide viewing angle, bendability and active illumination, and has been highly valued by the scientific community and the industry. Its application in display, lighting and other aspects has great potential. Electroluminescence and electrophosphorescence are referred to as first generation and second generation OLEDs, respectively. OLED based on fluorescent materials has high stability, but is limited by the law of quantum statistics. Under the action of electric start, the ratio of singlet excitons to triplet excitons is 1:3, so the fluorescent material The internal quantum efficiency of electroluminescence is only 25%. The phosphorescent material has a spin-orbit coupling effect of heavy atoms, which can comprehensively utilize singlet excitons and triplet excitons. The theoretical internal quantum efficiency can reach 100%, but the phosphorescent-based OLED has a significant efficiency roll-off effect. There are certain obstacles in high-brightness applications. In addition, phosphorescent materials require the use of expensive metals such as Pt, Ir, etc., so the price of phosphorescent materials is relatively high. At present, the guest materials in OLED devices mainly use phosphorescent materials.
磷光材料可以綜合利用單線態激子和三線態激子,實現100%的內量子效率。然而,由於過渡金屬配合物的激發態激子壽命相對過長,導致三 線態-三線態(T1-T1)在器件實際工作中淬滅。為了克服這個問題,研究者們常將磷光材料摻雜於有機主體材料中。因此,對於高效有機發光二極體,開發高性能的主體材料以及客體材料十分重要。 Phosphorescent materials can utilize singlet excitons and triplet excitons in combination to achieve 100% internal quantum efficiency. However, since the excited state exciton lifetime of the transition metal complex is relatively long, resulting in three The linear-triplet (T1-T1) is quenched in the actual operation of the device. To overcome this problem, researchers often dope phosphorescent materials into organic host materials. Therefore, for high-efficiency organic light-emitting diodes, it is important to develop high-performance host materials as well as guest materials.
目前,廣泛應用於磷光器件的主體材料為CBP(4,4’-二(9-咔唑基)聯苯),但是它要求的驅動電壓較高、玻璃化轉變溫度(Tg)低(Tg=62℃),易於結晶。另外,CBP是一種P型材料,空穴遷移率遠高於電子遷移率,不利於載流子注入和傳輸平衡,且發光效率低。 At present, the main material widely used in phosphorescent devices is CBP (4,4'-bis(9-carbazolyl)biphenyl), but it requires a higher driving voltage and a lower glass transition temperature (T g ) (T g = 62 ° C), easy to crystallize. In addition, CBP is a P-type material, the hole mobility is much higher than the electron mobility, which is not conducive to carrier injection and transmission balance, and the luminous efficiency is low.
針對現有主體(CBP)材料要求的驅動電壓較高、玻璃化轉變溫度易於結晶、載流子注入和傳輸不平衡等問題,本發明提供一種有機電致發光器件,其發光層主體材料為雙極性主體材料,該材料以螺[芴-9,2’-咪唑]作為強拉電子中心核,具有強給電子能力的二苯胺類、咔唑、吖啶等衍生物作為連接基團,形成D-A型、D-A-D型雙極性材料。 The present invention provides an organic electroluminescent device with a high driving voltage, a glass transition temperature, a crystallization, a carrier injection, and a transmission imbalance. The main body of the luminescent layer is bipolar. The host material, which uses spiro[芴-9,2'-imidazole] as the central core of the strong electrons, and has a strong electron donating ability such as diphenylamines, carbazoles, acridines and the like as a linking group to form a DA type. , DAD type bipolar material.
有機電致發光器件,包括陰極、陽極和有機層,所述有機層為空穴阻擋層、電子傳輸層、發光層中的一層或多層,所述有機層具有式(I)所述結構的化合物,
其中,R1、R2、R3表示為C1-C4烷基或烷氧基取代或未取代的吖啶基、吩噻嗪基、咔唑基、二苯胺基,氫,鹵素,C1-C4的烷基,R1、R2、R3至少一個為C1-C4烷基取代或未取代的吖啶基、吩噻嗪基、咔唑基、二苯胺基。 Wherein R 1 , R 2 , R 3 are represented by C1-C4 alkyl or alkoxy substituted or unsubstituted acridinyl, phenothiazine, carbazolyl, diphenylamino, hydrogen, halogen, C1-C4 The alkyl group, at least one of R 1 , R 2 and R 3 is a C1-C4 alkyl-substituted or unsubstituted acridinyl group, a phenothiazine group, a carbazolyl group or a diphenylamino group.
優選:R1表示為C1-C4烷基或烷氧基取代或未取代的吖啶基、吩噻嗪基、咔唑基、二苯胺基,R2、R3中至少一個為C1-C4烷基或烷氧基取代或未取代的吖啶基、吩噻嗪基、咔唑基、二苯胺基,其餘為氫或C1-C4的烷基。 Preferably, R 1 represents a C1-C4 alkyl group or an alkoxy substituted or unsubstituted acridinyl group, a phenothiazine group, a carbazolyl group, a diphenylamino group, and at least one of R 2 and R 3 is a C1-C4 alkane. Alkyl or alkoxy substituted or unsubstituted acridinyl, phenothiazine, carbazolyl, diphenylamino, the balance being hydrogen or a C1-C4 alkyl group.
優選:R1、R3為C1-C4烷基或烷氧基取代或者未取代的吖啶基、吩噻嗪基、咔唑基、二苯胺基。 Preferably, R 1 and R 3 are a C1-C4 alkyl group or an alkoxy-substituted or unsubstituted acridinyl group, a phenothiazine group, an oxazolyl group, or a diphenylamino group.
優選:R1、R3相同。 Preferably, R 1 and R 3 are the same.
式(I)所述的化合物具有下列結構:
所述式(I)所述的化合物為發光層的材料。 The compound of the formula (I) is a material of the light-emitting layer.
本發明的電子器件有機層的總厚度為1-1000nm,優選1-500nm,更優選5-300nm。 The organic layer of the electronic device of the present invention has a total thickness of from 1 to 1000 nm, preferably from 1 to 500 nm, more preferably from 5 to 300 nm.
所述有機層可以通過蒸渡或旋塗形成薄膜。 The organic layer may be formed into a film by steaming or spin coating.
如上面提到,本發明的式(I)所述的化合物如下,但不限於所列舉的結構:
上述雙極材料的製備方法,包括以下製備步驟:首先將鹵素取代芳基乙二酮與鹵素取代或未取代的9-芴酮在醋酸銨和乙酸條件下反應,得到鹵素取代的4’,5’-二芳基螺(芴-9,2’-咪唑),最後鹵素取代的4’,5’-二芳基螺(芴-9,2’-咪唑)與C1-C4烷基或烷氧基取代或未取代的吖啶、吩噻嗪基、咔唑基、二苯胺基通過鈀催化的Buchwald反應,得到所述的雙極性主體材料。 The preparation method of the above bipolar material comprises the following steps: firstly reacting a halogen-substituted arylethanedione with a halogen-substituted or unsubstituted 9-fluorenone under ammonium acetate and acetic acid to obtain a halogen-substituted 4',5. '-Diaryl spiro (芴-9,2'-imidazole), the last halogen-substituted 4',5'-diaryl spiro (芴-9,2'-imidazole) and C1-C4 alkyl or alkoxy The disubstituted or unsubstituted acridine, phenothiazine, carbazolyl, and diphenylamine groups are subjected to a palladium catalyzed Buchwald reaction to give the bipolar host material.
實驗表明,本發明的器件由於採用的雙極主體材料具有較高的玻璃化轉變溫度(Tg=158℃),雙極主體材料有利於載流子注入和傳輸平衡,因此發光效率高,使用壽命長。 Experiments show that the device of the present invention has a high glass transition temperature (T g = 158 ° C) due to the bipolar host material used, and the bipolar host material is advantageous for carrier injection and transmission balance, so the luminous efficiency is high, and the use is high. long life.
10‧‧‧玻璃基板 10‧‧‧ glass substrate
20‧‧‧陽極 20‧‧‧Anode
30‧‧‧空穴注入層 30‧‧‧ hole injection layer
40‧‧‧空穴傳輸層 40‧‧‧ hole transport layer
50‧‧‧發光層 50‧‧‧Lighting layer
60‧‧‧空穴阻擋層 60‧‧‧ hole blocking layer
70‧‧‧電子傳輸層 70‧‧‧Electronic transport layer
80‧‧‧電子注入層 80‧‧‧electron injection layer
90‧‧‧陰極 90‧‧‧ cathode
圖1為化合物2的DSC曲線;以及圖2為本發明的器件結構圖,其中10代表為玻璃基板,20代表為陽極,30代表為空穴注入層,40代表為空穴傳輸層,50代表發光層,60代表為空穴阻擋層,70代表為電子傳輸層,80代表為電子注入層,90代表為陰極。 1 is a DSC curve of Compound 2; and FIG. 2 is a structural view of the device of the present invention, wherein 10 represents a glass substrate, 20 represents an anode, 30 represents a hole injection layer, 40 represents a hole transport layer, and 50 represents a hole transport layer. The luminescent layer, 60 represents a hole blocking layer, 70 represents an electron transporting layer, 80 represents an electron injecting layer, and 90 represents a cathode.
下面結合實施例對本發明作進一步詳細的描述,但本發明的實施方式不限於此。 The present invention will be further described in detail below with reference to the embodiments, but the embodiments of the present invention are not limited thereto.
合成路線如下所示:
具體合成步驟為:秤取1-(4-溴苯基)-2-苯基乙基-1,2-二酮(14.5g,50mmol)(a1)(通過Sonogashira偶聯反應,再氧化製備),9-芴酮(7.2g,40mmol)(b1),醋酸銨(19.2g,250mmol),150mL冰醋酸於250mL的圓底燒瓶中,升溫至回流反應攪拌16小 時。反應結束後,自然冷卻至室溫,倒入200mL純淨水中,析出黃色固體。砂芯漏斗抽濾,水洗。矽膠柱層析分離得到9.9g黃色固體。產率:55%。 The specific synthetic procedure is as follows: 1-(4-bromophenyl)-2-phenylethyl-1,2-dione (14.5 g, 50 mmol) (a1) (prepared by Sonogashira coupling reaction, reoxidation) , 9-fluorenone (7.2 g, 40 mmol) (b1), ammonium acetate (19.2 g, 250 mmol), 150 mL of glacial acetic acid in a 250 mL round bottom flask, warmed to reflux and stirred for 16 min. Time. After completion of the reaction, it was naturally cooled to room temperature, poured into 200 mL of purified water to precipitate a yellow solid. The core funnel was suction filtered and washed. Separation by gel column chromatography gave 9.9 g of a yellow solid. Yield: 55%.
其合成路線見圖1所示。 The synthetic route is shown in Figure 1.
具體合成步驟為:秤取4’-(4-溴苯基)-5’-苯基螺(芴-9,2’-咪唑)(0.9g,2mmol)(c1),9,9-二甲基-9,10-二氫吖啶(0.46g,2.2mmol)(d1),Pd2(dba)3(0.18g,0.2mmol),NaOtBu(0.39g,4mmol)於25mL三口燒瓶中,換氮氣三次。三叔丁基膦甲苯溶液(0.15g,0.42mmol)溶於10mL乾燥的甲苯中,注入到反應瓶中。升溫回流16小時。反應結束後,加入5%的亞硫酸氫鈉溶液,二氯甲烷萃取,合併有機層,無水硫酸鎂乾燥。砂芯漏斗過濾,旋乾溶劑,以正己烷:乙酸乙酯=10:1為洗脫劑,矽膠層析柱提純,分離得到1.03g黃色粉末固體。再用4mL二氯甲烷溶解,加入20mL甲醇,放置於5℃冰箱析晶,得到0.85g黃色晶體。產率:73%。產物鑒定資料如下: 1H NMR(400MHz,CDCl3)δ=8.02-7.94(m,J=8.3Hz,2 H),7.80(d,J=7.1Hz,2 H),7.83(d,J=7.8Hz,2 H),7.53(d,J=7.3Hz,1 H),7.51-7.37(m,8 H),7.30-7.22(m,2 H),7.05-6.90(m,6 H),6.37-6.31(m,J=8.1Hz,2 H).13C NMR(100MHz,CDCl3)δ=168.5,167.9,143.7,142.4,140.6,138.7,132.2,132.1,131.9,131.5,131.0,130.3,129.8,129.2,128.6,128.0,126.4,125.4,123.2,121.0,121.0,114.1,110.3,53.5,36.1,31.2ppm.Ms(ESI:Mz 577)(M+1) The specific synthetic steps are: weighing 4'-(4-bromophenyl)-5'-phenylspiro(芴-9,2'-imidazole) (0.9g, 2mmol) ( c1 ), 9,9-dimethyl Base-9,10-dihydroacridine (0.46 g, 2.2 mmol) ( d1 ), Pd 2 (dba) 3 (0.18 g, 0.2 mmol), NaOtBu (0.39 g, 4 mmol) in a 25 mL three-neck flask, with nitrogen three times. A solution of tri-tert-butylphosphine in toluene (0.15 g, 0.42 mmol) was dissolved in 10 mL of dry toluene and poured into a reaction flask. The temperature was refluxed for 16 hours. After the reaction was completed, a 5% solution of sodium hydrogensulfite was added, and the mixture was extracted with dichloromethane. The mixture was filtered through a celite funnel, and the solvent was evaporated to dryness eluting with hexane: ethyl acetate = 10:1 as eluent. Further, it was dissolved in 4 mL of dichloromethane, and 20 mL of methanol was added thereto, and the mixture was allowed to stand in a refrigerator at 5 ° C to obtain 0.85 g of a yellow crystal. Yield: 73%. The product identification data is as follows: 1 H NMR (400 MHz, CDCl 3 ) δ = 8.02 - 7.94 (m, J = 8.3 Hz, 2 H), 7.80 (d, J = 7.1 Hz, 2 H), 7.83 (d, J = 7.8 Hz, 2 H), 7.53 (d, J = 7.3 Hz, 1 H), 7.51-7.37 (m, 8 H), 7.30-7.22 (m, 2 H), 7.05-6.90 (m, 6 H), 6.37-6.31 (m, J = 8.1 Hz, 2 H). 13 C NMR (100 MHz, CDCl 3 ) δ = 168.5, 167.9, 143.7, 142.4, 140.6, 138.7, 132.2, 132.1, 131.9, 131.5, 131.0, 130.3, 129.8, 129.2, 128.6, 128.0, 126.4, 125.4, 123.2, 121.0, 121.0, 114.1, 110.3, 53.5, 36.1, 31.2 ppm. Ms (ESI: Mz 577) (M+1)
合成路線如下所示:
秤取1-(4-溴苯基)-2-苯基乙基-1,2-二酮(4.34g,15mmol)(a1)(通過Sonogashira偶聯反應,再氧化製備),2-溴-9-芴酮(3.89g,15mmol),醋酸銨(5.8g,75mmol),30mL冰醋酸於50mL的圓底燒瓶中,升溫至回流反應攪拌16小時。反應結束後,自然冷卻至室溫,倒入100mL純淨水中,析出黃色固體。砂芯漏斗抽濾,水洗。矽膠柱層析分離得到4.1g黃色固體。產率:52%。 Weigh 1-(4-bromophenyl)-2-phenylethyl-1,2-dione (4.34 g, 15 mmol) (a1) (prepared by Sonogashira coupling reaction, reoxidation), 2-bromo- 9-fluorenone (3.89 g, 15 mmol), ammonium acetate (5.8 g, 75 mmol), 30 mL of glacial acetic acid in a 50 mL round bottom flask, warmed to reflux and stirred for 16 hours. After completion of the reaction, it was naturally cooled to room temperature, poured into 100 mL of purified water to precipitate a yellow solid. The core funnel was suction filtered and washed. Separation by gel column chromatography gave 4.1 g of a yellow solid. Yield: 52%.
合成路線如下所示:
具體合成步驟為:秤取2-溴-4’-(4-溴苯基)-5’-苯基螺(芴-9,2’-咪唑)(1g,1.9mmol)(c2),9,9-二甲基-9,10-二氫吖啶(0.79g,3.8mmol)(d1),Pd2(dba)3(0.18g,0.2mmol),NaOtBu(0.73g,7.6mmol)於25mL三口燒瓶中,換氮氣三次。三叔丁基膦甲苯溶液(0.12g,0.6mmol)溶於10mL乾燥的甲苯中,注入到反應瓶中。升溫回流16小時。反應結束後,加入5%的亞硫酸氫鈉溶液,二氯甲烷萃取,合併有機層,無水硫酸鎂乾燥。砂芯漏斗過濾,旋乾溶劑,以正己烷:乙酸乙酯=10:1為洗脫劑,矽膠層析柱提純,分離得到1.35g黃色粉末固體。再用4mL二氯甲烷溶解,加入20mL甲醇,放置於5℃冰箱析晶,得到1.1g黃色晶體。產率:73%。產物鑒定資料如下:1H NMR(400MHz,CDCl3)δ=8.08(d,J=7.9Hz,1 H),7.95-7.87(m,3 H),7.72(d,J=7.2Hz,2 H),7.56-7.48(m,2 H),7.48-7.41(m,7 H),7.38(d,J=8.3Hz,2 H),7.32(s,1 H),7.04-6.86(m,10 H),6.43-6.36(m,2 H),6.34-6.27(m,2 H),1.67(s,12 H)ppm.13C NMR(100MHz,CDCl3)δ=168.9,168.3,143.8,142.5,141.7,141.5,140.8,140.7,140.5,139.1,133.1,131.9,131.7,131.5,131.1,130.3,130.1,129.9,129.2,128.6,128.4,126.5,126.5,126.4,125.4,125.3,123.3,123.1,121.3,120.9,120.7,114.3,114.1,110.0,,53.5,36.0,36.0,31.6,31.2ppm.Ms(ESI:Mz 784)(M+1)。Tg=158℃。 The specific synthetic procedure is as follows: 2-bromo-4'-(4-bromophenyl)-5'-phenylspiro(芴-9,2'-imidazole) (1 g, 1.9 mmol) ( c2 ), 9, 9-Dimethyl-9,10-dihydroacridine (0.79 g, 3.8 mmol) ( d1 ), Pd 2 (dba) 3 (0.18 g, 0.2 mmol), NaOtBu (0.73 g, 7.6 mmol) in 25 mL three In the flask, change the nitrogen three times. A solution of tri-tert-butylphosphine in toluene (0.12 g, 0.6 mmol) was dissolved in 10 mL of dry toluene and poured into a reaction flask. The temperature was refluxed for 16 hours. After the reaction was completed, a 5% solution of sodium hydrogensulfite was added, and the mixture was extracted with dichloromethane. The mixture was filtered through a celite funnel, and the solvent was evaporated to dryness eluting with hexane: ethyl acetate = 10:1 as eluent. Further, it was dissolved in 4 mL of dichloromethane, and 20 mL of methanol was added thereto, and the mixture was allowed to stand in a refrigerator at 5 ° C to obtain 1.1 g of yellow crystals. Yield: 73%. The product identification data are as follows: 1 H NMR (400 MHz, CDCl 3 ) δ = 8.08 (d, J = 7.9 Hz, 1 H), 7.95-7.87 (m, 3 H), 7.72 (d, J = 7.2 Hz, 2 H ), 7.56-7.48 (m, 2 H), 7.48-7.41 (m, 7 H), 7.38 (d, J = 8.3 Hz, 2 H), 7.32 (s, 1 H), 7.04-6.86 (m, 10) H), 6.43-6.36 (m, 2 H), 6.34-6.27 (m, 2 H), 1.67 (s, 12 H) ppm. 13 C NMR (100 MHz, CDCl 3 ) δ = 168.9, 168.3, 143.8, 142.5 , 141.7, 141.5, 140.8, 140.7, 140.5, 139.1, 133.1, 131.9, 131.7, 131.5, 131.1, 130.3, 130.1, 129.9, 129.2, 128.6, 128.4, 126.5, 126.5, 126.4, 125.4, 125.3, 123.3, 123.1, 121.3 , 120.9, 120.7, 114.3, 114.1, 110.0, 53.5, 36.0, 36.0, 31.6, 31.2 ppm. Ms (ESI: Mz 784) (M+1). T g = 158 ° C.
氮氣保護下,以20℃/min的加熱和冷卻速率用示差掃描量熱法(DSC)測試化合物2的玻璃化轉變溫度。測得化合物2的玻璃化轉變溫度Tg為158℃(圖1)。而文獻所報導的CBP的玻璃化轉變溫度僅為62℃。 The glass transition temperature of Compound 2 was tested by differential scanning calorimetry (DSC) at a heating and cooling rate of 20 ° C/min under nitrogen atmosphere. The glass transition temperature T g of Compound 2 was measured to be 158 ° C ( FIG. 1 ). The glass transition temperature of CBP reported in the literature is only 62 °C.
可見,本發明中的化合物比常用主體材料CBP具有更高的玻璃化轉變溫度,本發明顯著提高了主體材料的熱穩定性。 It can be seen that the compound of the present invention has a higher glass transition temperature than the conventional host material CBP, and the present invention remarkably improves the thermal stability of the host material.
器件結構為ITO/MoO3(10nm)/NPB(40nm)/化合物2:Ir(ppy):(7wt%,30nm)/BCP(10nm)/Alq3(30nm)/LiF(1nm)/AL(100nm)(見圖2) The device structure is ITO/MoO 3 (10 nm) / NPB (40 nm) / compound 2 : Ir (ppy): (7 wt%, 30 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / AL (100 nm ) (see Figure 2)
首先,將透明導電ITO玻璃基板(包含10和20)按照以下步驟處理:預先用洗滌劑溶液、去離子水,乙醇,丙酮,去離子水洗淨,再經氧等離子處理30秒。 First, the transparent conductive ITO glass substrate (including 10 and 20) was treated as follows: previously washed with a detergent solution, deionized water, ethanol, acetone, deionized water, and then subjected to oxygen plasma treatment for 30 seconds.
然後,在ITO上蒸渡10nm厚的MoO3作為空穴注入層30。 Then, 10 nm thick MoO 3 was vapor-deposited on the ITO as the hole injection layer 30.
然後,在空穴注入層上蒸渡40nm厚的NPB作為空穴傳輸層40。 Then, a 40 nm-thick NPB was vapor-deposited on the hole injection layer as the hole transport layer 40.
然後,在空穴傳輸層上蒸渡30nm厚的化合物2:Ir(ppy):(7wt%)作為發光層50。 Then, a compound 2 of 2 nm thick: Ir(ppy): (7 wt%) was vapor-deposited on the hole transport layer as the light-emitting layer 50.
然後,在發光層上蒸渡10nm厚的BCP作為空穴阻擋層60。 Then, a BCP having a thickness of 10 nm was vapor-deposited on the light-emitting layer as the hole blocking layer 60.
然後,在空穴阻擋層上蒸渡30nm厚的Alq3作為電子傳輸層70。 Then, 30 nm thick Alq 3 was vapor-deposited on the hole blocking layer as the electron transport layer 70.
然後,在電子傳輸層上蒸渡1nm厚的Alq3作為電子注入層80。 Then, 1 nm thick Alq 3 was vaporized on the electron transport layer as the electron injection layer 80.
最後,在電子注入層上蒸渡100nm厚的鋁作為器件陰極90。 Finally, 100 nm thick aluminum was vaporized on the electron injecting layer as the device cathode 90.
所製備的器件在20mA/cm2的工作電流密度下,亮度5224cd/m2,電流效率為26.12cd/A,發射綠光CIEx為0.307,CIEy為0.620。 Devices prepared in operating current density 20mA / cm 2, the luminance of 5224cd / m 2, the current efficiency was 26.12cd / A, green light emission of CIEx 0.307, CIEy of 0.620.
器件結構為ITO/MoO3(10nm)/NPB(40nm)/CBP:Ir(ppy):(7wt%,30nm)/BCP(10nm)/Alq3(30nm)/LiF(1nm)/AL(100nm) The device structure is ITO/MoO 3 (10 nm) / NPB (40 nm) / CBP: Ir (ppy): (7 wt%, 30 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / AL (100 nm)
方法同實施例4,但使用常用市售化合物CBP作為主體材料,製作對比用電致發光有機半導體二極體器件。 The method was the same as in Example 4 except that a commonly used commercially available compound CBP was used as a host material to prepare a comparative electroluminescent organic semiconductor diode device.
所製備的器件在20mA/cm2的工作電流密度下,亮度3875cd/m2,電流效率為19.38cd/A,發射綠光CIEx為0.312,CIEy為0.620。 Devices prepared in operating current density 20mA / cm 2, the luminance of 3875cd / m 2, the current efficiency was 19.38cd / A, green light emission of CIEx 0.312, CIEy of 0.620.
通過對比實施例4和比較例的實驗結果可見,本發明中的雙極主體材料相比於廣泛使用的主體材料CBP,更利於載流子注入和傳輸平衡,使用本發明的有機材料製備的器件具有更好的電致發光性能,更符合高性能有機半導體器件對主體材料的要求。 By comparing the experimental results of Example 4 and the comparative example, it can be seen that the bipolar host material of the present invention is more advantageous for carrier injection and transport balance than the widely used host material CBP, and the device prepared using the organic material of the present invention. It has better electroluminescence properties and is more in line with the requirements of high performance organic semiconductor devices for host materials.
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