TWI612030B - 有機電子發光材料 - Google Patents
有機電子發光材料 Download PDFInfo
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- TWI612030B TWI612030B TW105111987A TW105111987A TWI612030B TW I612030 B TWI612030 B TW I612030B TW 105111987 A TW105111987 A TW 105111987A TW 105111987 A TW105111987 A TW 105111987A TW I612030 B TWI612030 B TW I612030B
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- organic electroluminescent
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- 239000000463 material Substances 0.000 title claims abstract description 30
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 239000011737 fluorine Substances 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 15
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 12
- 229910052740 iodine Inorganic materials 0.000 claims description 12
- 239000011630 iodine Substances 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000005577 anthracene group Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- -1 4 -substituted benzene ring Chemical group 0.000 claims description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 125000004149 thio group Chemical group *S* 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 3
- 125000006575 electron-withdrawing group Chemical group 0.000 abstract description 2
- 230000009286 beneficial effect Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000011982 device technology Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- NQQVLNFSVPLPII-UHFFFAOYSA-N 1,1-dimethylguanidine;hydrochloride Chemical compound [Cl-].CN(C)C([NH3+])=N NQQVLNFSVPLPII-UHFFFAOYSA-N 0.000 description 1
- ATTVYRDSOVWELU-UHFFFAOYSA-N 1-diphenylphosphoryl-2-(2-diphenylphosphorylphenoxy)benzene Chemical compound C=1C=CC=CC=1P(C=1C(=CC=CC=1)OC=1C(=CC=CC=1)P(=O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(=O)C1=CC=CC=C1 ATTVYRDSOVWELU-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
- C07C225/14—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated
- C07C225/16—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
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- C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/38—[b, e]-condensed with two six-membered rings
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- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
- C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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Abstract
本發明涉及有機電子發光材料，具有化學式（I）的結構，本發明的化學式（I）類型的化合物具有高穩定性的吸電子基團與供電子基團，它們之間具有穩定的化學鍵，且不存在較強的共軛。這些特點使式（I）類化合物具有較高的螢光量子效率和良好的電荷傳輸能力，且更接近國際標準的深藍色，有利於實現更高色純度的全彩顯示器。
Description
本發明涉及新型的有機光電材料，通過真空蒸鍍、印刷、列印等方式形成薄膜，可應用於電致發光器件、薄膜電晶體、太陽能電池和光電感測器、氧氣濃度探測器，屬於有機光電材料領域。
有機電致發光器件作為一種新型的顯示技術，具有自發光、寬視角、低能耗、效率高、厚度薄、色彩豐富、回應速度快、可製作柔性與透明的發光器件等優點，因此有機電致發光器件技術可以應用在新型平板顯示器、面光源照明及可穿戴設備等應用領域，也可以作為LCD的背光源。
經過多年的發展，有機電致發光器件技術(OLED)已經達到市場化水準。但目前廣泛使用的高效率磷光材料需要用到銥、鉑等稀有貴重金屬而成本高昂，是OLED成本高居不下的重要因素之一。為了降低OLED材料的成本，開發可以充分利用電激發器件中三線態能級的低成本、高穩定性材料，例如具有熱激發延遲螢光的化合物，是有希望解決高性能OLED材料高成本問題的方法之一。
本發明的目的在於提供一種新型有機電致發光材料，並將其應用於有機光電器件，該材料具有較低的單線態與三線態之間的能級差，可作為有機電致發光器件中發光層的主體材料或客體材料，也可作為電子傳輸材料或空穴傳輸材料。使用該材料可獲得更接近國際標準的深藍色的電致發光器件，有利於實現更高色純度的全彩顯示器。
本發明所述的新型光電材料，具有化學式(I)的結構：
其中，Ar為未取代或者至少有一個R4取代的苯環、萘環、蒽環，n=1-3；D為含有氮原子的供電子基團，為以下基團中的一個：
R1具有1至20個碳原子的烷基，R3，R4各自獨立地選自氫H，氘D，氟F，氯Cl，溴Br，碘I，羥基OH，氰基CN，氨基NH2，硝基NO2，具有1至20個碳原子的烷基，具有1至20個碳原子的烷氧基，具有1至20個碳原子的烷硫基，C6-C40
的含一個或者多個取代基R5取代或者未取代的芳基，C6-C40的含一個或者多個取代基R5取代或者未取代的芳烴基，C5-C40的含一個或者多個取代基R5取代或者未取代的含有一個或者多個雜原子的雜芳基；R5選自氟F，氯Cl，溴Br，碘I，羥基OH，氰基CN，氨基NH2，硝基NO2，具有1至20個碳原子的烷基；所述雜原子為O，S，N。
優選地，R1具有1至4個碳原子的烷基，R3，R4各自獨立地選自氫H，氟F，氯Cl，溴Br，碘I，羥基OH，氰基CN，氨基NH2，硝基NO2，具有1至4個碳原子的烷基，具有1至4個碳原子的烷氧基，具有1至4個碳原子的烷硫基，C6-C25的含一個或者多個取代基R5取代或者未取代的芳基，C6-C25的含一個或者多個取代基R5取代或者未取代的芳烴基，C5-C25的含一個或者多個取代基R5取代或者未取代的含有一個或者多個雜原子的雜原子芳基；R5選自氫H，氟F，氯Cl，溴Br，碘I，羥基OH，氰基CN，氨基NH2，硝基NO2，具有1至4個碳原子的烷基；所述雜原子為O，S，N；Ar為未取代或有一個R4取代的苯環、萘環、蒽環。
更優選地，R1具有1至4個碳原子的烷基，R3,R4各自獨立地選自氫H，氟F，氯Cl，溴Br，具有1至4個碳原子的烷基，C6-C25的含一個或者多個取代基R5取代或者未取代的芳基，C6-C25的含一個或者多個取代基R5取代或者未取代的芳烴基，C5-C25的含一個或者多個取代基R5取代或者未取代的含有一個或者多個雜原子的雜原子芳基；R5選自氫H，氟F，氯Cl，溴Br，具有1至4個碳原子的烷基；所述雜原子為O，S，N。
進一步優選：R1選自具有1至4個碳原子的烷基；R3選自氫H，氟F，氯Cl，溴Br，碘I，具有1至4個碳原子的烷基，含一個或者多個取代基R5取代或者未取代的苯基、萘基或蒽基；R4選自氫H，氟F，氯Cl，溴Br，碘I，具有1至4個碳原子的烷基，苯基，萘基；R5選自氫H，具有1至4個碳原子的烷基。
特別優選：R1選自具有1至4個碳原子的烷基；R3選自氫H，具有1至4個碳原子的烷基，苯基，萘基；R4選自氫H，具有1至4個碳原子的烷基，苯基，萘基。
下面列出優選的化合物進一步闡明本發明。它們不應被視為以任何方式限制本發明。
再優選：
本發明的具有化學式(I)類型的化合物具有高穩定性的吸電子基團與供電子基團，它們之間具有穩定的化學鍵，且不存在較強的共軛。這些特點使式(I)類化合物具有較高的螢光量子效率和良好的電荷傳輸能力，實驗表明，更接近國際標準的深藍色，有潛力應用於有機電致發光器件領域。
本發明的具有結構式(I)的化合物具有剛性分子結構和較少的非輻射退激發途徑，其不對稱的donor-acceptor結構具有小的單線態-三線態能隙，從而獲得高的發光效率；同時，本發明的具有能傳輸電子或空穴的基團。以上特點使得本發明的化合物可以用於有機電致發光器件、有機薄膜電晶體、有機太陽能電池和有機光電感測器等領域。
10‧‧‧玻璃基板
20‧‧‧陽極ITO
30‧‧‧為空穴傳輸層
40‧‧‧電子/激子阻擋層
50‧‧‧為發光層
60‧‧‧為激子阻擋層
70‧‧‧為電子傳輸層
80‧‧‧為電子注入層
90‧‧‧為陰極
圖1為本發明的器件結構圖。
圖2為化合物1的1H-NMR圖。
下面結合實施例對本發明做進一步的詳細說明。但不應被視為以任何方式限制本發明。
實施例1：化合物1的合成
向反應容器中依次加入2g(0.018mol)二甲氨基甲醯氯，20ml四氫呋喃溶劑，對裝置進行除氧、通入氮氣保護，冷卻降溫至反應液溫度至-75~-65℃，緩慢滴加10ml 1.6M n-BuLi/THF溶液，控制反應液溫度在-75~-65℃，滴加完畢後，繼續保持此溫度反應0.5-1h。後將6g化合物1-1滴加進去，控制反應液溫度在-75~-65℃，滴加完畢後，繼續保持此溫度反應0.5-1h，後反應液移至室溫自然升溫反應4-6h，停止反應。加入乙酸乙酯/去離子水萃取，水層再用乙酸乙酯萃取，合併有機層，無水硫酸鎂乾燥，抽濾，濾液濃縮得到灰白色固體。將得到的固體進行柱層析，得到白色固體粉末3g。
實施例2：下面是本發明化合物的應用實例。
器件結構如圖1。器件製備方式：首先，將透明導電ITO玻璃(帶有陽極20的玻璃基板10)依次經洗滌劑溶液、去離子水、丙酮超聲清洗，異丙醇蒸汽清洗，再用氧氣等離子處理5分鐘。
然後，在ITO上蒸鍍35nm厚的NPB作為空穴傳輸層30。
然後，蒸鍍5nm厚的mCP作為電子/激子阻擋層40。
然後，蒸鍍20nm厚的發光層50，以mCP作為主體材料，本發明的化合物1作為摻雜材料，摻雜濃度為3%。
然後，蒸鍍10nm厚的mCP作為激子阻擋層60。
然後，蒸鍍30nm厚的TPBi作為電子傳輸層70。
最後，蒸鍍1nm厚的LiF作為電子注入層80和100nm Al作為陰極90。
本發明所製備的有機電致發光器件發射近紫外光，發射波長在416nm，色座標為(0.17,0.09)。
比較例
比較例採用文獻Angew.Chem.Int.Ed.2014,53,6402-6406中報導的化合物Cz2BP代替化合物1，器件結構與文獻中一致，且與實施例6中的器件結構基本相同，除了主體材料及激子阻擋材料採用DPEPO。比較例製備的有機電致發光器件發射波長在446nm，色座標為(0.16,0.14)。
因此，本發明的材料相比較已報導材料，具有更加接近於國家電視標準委員會(National Television Standards Committee，NTSC)關於深藍光的標準(0.14,0.08)的色座標。
Claims (8)
- 一種有機電子發光材料，具有化學式(I)的結構：
- 如申請專利範圍第1項所述的有機電子發光材料，其中R1具有3個碳原子的烷基，R3，R4各自獨立地選自氫H，氟F，氯Cl，溴Br，碘I，羥基OH，氰基CN，氨基NH2，硝基NO2，具有1至4個碳原子的烷基，具有1至4個碳原子的烷氧基，具有1至4個碳原子的烷硫基，C6-C25的含一個或者多個取代基R5取代或者未取代的芳基，C6-C25的含一個或者多個取代基R5取代或者未取代的芳烴基，C5-C25的含一個或者多個取代基R5取代或者未取代的含有一個或者多個雜原子的雜原子芳基；R5選自氫H，氟F，氯Cl，溴Br，碘I，羥基OH，氰基CN，氨基NH2，硝基NO2，具有1至4個碳原子的烷基；所述雜原子為O，S，N；Ar為未取代或有一個R4取代的苯環、萘環、蒽環。
- 如申請專利範圍第2項所述的有機電子發光材料，其中R1具有3個碳原子的烷基，R3,R4各自獨立地選自氫H，氟F，氯Cl，溴Br，具有1至4個碳原子的烷基，C6-C25的含一個或者多個取代基R5取代或者未取代的芳基，C6-C25的含一個或者多個取代基R5取代或者未取代的芳烴基，C5-C25的含一個或者多個取代基R5取代或者未取代的含有一個或者多個雜原子的雜原子芳基；R5選自氫H，氟F，氯Cl，溴Br，具有1至4個碳原子的烷基；所述雜原子為O，S，N。
- 如申請專利範圍第3項所述的有機電子發光材料，其中R1選自具有3個碳原子的烷基；R3選自氫H，氟F，氯Cl，溴Br，碘I，具有1至4個碳原子的烷基，含一個或者多個取代基R5取代或者未取代的苯基、萘基或蒽基；R4選自氫H，氟F，氯Cl，溴Br，碘I，具有1至4個碳原子的烷基，苯基，萘基；R5選自氫H，具有1至4個碳原子的烷基。
- 如申請專利範圍第4項所述的有機電子發光材料，其中R1選自具有3個碳原子的烷基；R3選自氫H，具有1至4個碳原子的烷基，苯基，萘基；R4選自氫H，具有1至4個碳原子的烷基，苯基，萘基。
- 如申請專利範圍第5項所述的有機電子發光材料，為下列化合物的一個：
- 如申請專利範圍第2項所述的有機電子發光材料，為下列化合物：
- 如申請專利範圍第1至7項中之任一項所述的有機電子發光材料，其中，係被使用在有機電致發光器件上的應用。
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