TW200907013A - Triptycene derivatives and their application - Google Patents

Abstract

The present invention discloses a triptycene derivative and the application thereof for the host luminescence material; the electron transporting material or the hole transport material in the organic electronic device. The above-mentioned triptycene derivative has a normal structure shown as follows, wherein R1-R12 may be the same or different, and are distinctly selected from aromatics containing one or more substituent groups; heteroaromatics containing one or more substituent groups or non-aromatics containing one or more substituent groups.

Description

200907013 IX. DESCRIPTION OF THE INVENTION: TECHNICAL FIELD OF THE INVENTION The present invention relates to a conjugated compound, particularly to triptycene derivatives and uses thereof. [Prior Art] Phosphorescent metal complexes have recently been used as phosphorescent dopants for organic light-emitting diodes. Among these metal complexes used as the light-emitting layer in the organic light-emitting diode, the ring metallization of the base metal complex has caused the most extensive research due to the strong spin 'orbital coupling of the electronic configuration. Due to the spin-domain coupling, the single- and triple-excited states are mixed, thus shortening the lifetime of the triplet and increasing the phosphorescence efficiency. In addition, it is found that the use of doping (d〇ping) can improve the efficiency of the component, so the way of phosphorescent material is mixed in the host material, and the blue phosphorescent host material gradually becomes the focus of research, which was reported in the previous literature. Phosphorescent host materials are mainly carbazole-(Carbaz〇le), and carbazole derivatives have high triplet energy and are suitable for use as a host material for blue phosphorescence. In view of this, the development of new carbazole derivatives with high triplet energy to extend the life of components and improve luminous efficiency is still a subject worthy of industrial attention. Citations: 1. Synthesis and Structure of 2,6,14- and 2,7,14- Trisunstituted Triptycene Derivatives., Chun Zhang; Chuan-Feng Chen, J. Org. Chem. 2006, 71, 6626-6629 SUMMARY OF THE INVENTION In view of the above-mentioned background, in order to meet industrial requirements, the present invention provides a novel triptycene derivative and its use as a host material and electron conduction in organic electronic components. Application of an electronic transport material or a hole transport material. It is an object of the present invention to provide a triptycene derivative having a high thermal stability to enhance the service life of an organic electronic component. Another object of the present invention is to provide a conjugated compound having a diphenylnonane structure having a high triplet energy level difference to complement the existing energy level which is generally not applicable to a blue phosphorescent main layer material. Poor and common types of phosphorescent materials such as iridium (Ir), platinum (Pt), bismuth (〇s) and other red, blue, green metal complex materials, according to which, in order to achieve economic benefits and industry The effectiveness of the use of. In accordance with the above objects, the present invention discloses a triptycene derivative and its use as a primary illuminant material, an electron conductive material or a hole conducting material in an organic electronic component. Wherein, the general structure of the above-mentioned triptycene derivative is as follows:

Wherein 'R1 to Rl2 may be the same or different, and R1 to R12 are independently selected from one of the following groups: an aromatic group having one or more substituents' having one or more 200907013 〇 [ [R17, R18 R2 〇

Aromatic heterocyclic group of a substituent, a non-aromatic ring having a R13 y R15 -B \ +N: R14 , R16 R13 / R15 s / \ ' 卜 R]4 , s \ R16 or more substituents The group, R19 having one or more substituents G may be one selected from the group consisting of: an aromatic group of 7 UHi jpe substituent, an aromatic heterocyclic group having one or more substituents, a heterocyclic group of one or more substituents. The book also discloses the application of the above three lion derivatives', especially for the main material, electron conductive material, hole conducting material and main illuminant used in organic electroluminescent elements and/or disc elements; Electronically conductive materials and hole conducting materials for other organic electronic components. [Embodiment] The direction of the present invention as discussed herein is a triple butterfly derivative structure and its application. In order to thoroughly understand the present invention, detailed process steps or constituent structures will be set forth in the following description. The invention is not limited to the specific details familiar to those skilled in the art. In other instances, well-known components or process steps are not described in detail to avoid unnecessarily limiting the invention. The preferred system of the present invention will be described in detail below, but the present invention can be widely applied to other systems in addition to the detailed description, and the scope of the present invention is not limited, and the scope of the following patents will prevail. Page 8 200907013 A first embodiment of the present invention discloses a triptycene derivative structure, and the general structure of the above-mentioned triptycene derivative structure is as follows: R6

Wherein R1 to R12 are the same or different and R1 to R12 are independently selected from one of the following groups: an aromatic group having one or more substituents; an aromatic heterocyclic group having one or more substituents. a non-aromatic ring group having one or more substituents;

The above substituent may be one selected from the group consisting of a hydrogen atom, a halogen atom (e.g., fluorine, chlorine, bromine, iodine); an aryl group, a halogen-substituted aryl group, a halogen-substituted arylalkyl group, an i-alkyl group. a substituted aryl group, a decyl-substituted arylalkyl group, an aryl-substituted C1-C20 alkyl group; an electron donating group such as a C1-C20 alkyl group, a C1-C20 cycloalkyl group (for example: hydrazine) Base, ethyl, butyl, cyclohexyl), C1-C20 alkoxy gmup, C1-C20 substituted amino group, substituted aromatic amine group [eg aniline] Or an electron withdrawing group such as a halogen, a nitrile, a nitro group, a carbonyl group, a cyano group, and a halogen-substituted cl_C2 alkyl group (for example, 9 pages 200907013 trifluoromethyl, cf3); heterocyclic substituent group. The above G may be one selected from the group consisting of an aromatic group having one or more substituents; an aromatic heterocyclic group having one or more substituents; and a heterocyclic ring having one or more substituents. Group. The substituent of the above G may be one selected from the group consisting of a hydrogen atom, a halogen atom (e.g., fluorine, gas, bromine, argon); an aryl group, a halogen-substituted aryl group, a halogen-substituted arylalkyl group, i An alkyl-substituted aryl group, a haloalkyl-substituted aromatic alkyl group, an aryl-substituted C1-C20 alkyl group; an electron donating group such as a C1-C20 alkyl group, a C1-C20 cycloalkyl group (for example: Methyl, ethyl, butyl, cyclohexyl), C1-C20 alkoxy group, C1-C20 substituted amino group, substituted aromatic amine group [eg aniline) )] or an electron withdrawing group such as halogen, nitrile, nitro, carbonyl, cyano (-CN) and halogen-substituted C1- C20 alkyl (e.g., trifluoromethyl, CF3); heterocyclic substituent. R13 to R21 may be the same or different, and R13 to R21 are independently selected from one of the following groups: a hydrogen atom; a C1-C20 alkyl group, a C1-C20 cycloalkyl group (e.g., methyl, ethyl, butyl). Alkyl, cyclohexyl); C1-C20 alkoxygroup; an amino group; an aromatic group having one or more substituents; an aromatic heterocyclic group having one or more substituents. The substituents of the above R13 to R21 are independently selected from one of the following groups: a hydrogen atom, a halogen atom, an aromatic group, a dentate-substituted aromatic group, a halogen-substituted aromatic group, a haloalkyl-substituted aryl group, and a halogen. Alkyl-substituted arylalkyl, aryl-substituted C1-C20 alkyl, C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkoxy group, C1-C20 substituted amine Amino group), an aromatic amine group having a substituent, or a C1-C20 alkyl group substituted with a halogen-substituted C1-C20 alkyl group (for example, a trifluoromethyl group) having a substituted electron substituent on page 10, 200907013 (electron withdrawing group). , CF3), a heterocyclic substituent group or a nitrile group, a nitro group; a carbonyl group; a cyano group (-CN). Further, it is to be noted that, in the triptycene derivative structure according to the present embodiment, R1 to R12 may not be hydrogen atoms at the same time. According to this embodiment, the above aromatic group may be selected from the group consisting of phenyl, naphthyl, diphenyl, anthryl, pyrenyl, phenanthryl. ) with a benzoene or other form of polyphenylene ring group. The above aromatic heterocyclic group may be selected from the group consisting of pyrane, pyroline, fliran, benzofUran, thiophene, benzophene. Benzothiophene, 0 pyridine, °f«#(quinoline), isoquinoline, "pyazine,pyrimidine,pyrpy,° Pyrazole, imidazole, indole, thiazole, isothiazole, oxazole, heterosexual (^32〇匕) ), benzothiazole 0^1^〇仙〇匕), benzoxazole as 61^(«&2〇16), 1,2,4-trioxazole (1,2,4-triazole) 1,2,3-3,0,0,3-triazole, 1,2,3,4-tetrazolium <»tetraazole, with phenanthroline, or It is another form of heteronuclear aromatic ring group. The above non-aromatic ring group may be one selected from the group consisting of: a hydrogen atom, a halogen atom (for example, fluorine, gas, bromine, iodine); a C1-C20 alkyl group, a C1-C20 cycloalkyl group ( For example: methyl, ethyl, butyl, cyclohexyl); C1-C20 alkoxy group; amino group; nitrile group; nitro group; carbonyl ( Carbonyl group); cyano group (_CN); halogen taken from page 11 200907013 C1-C20 alkyl (eg, trifluorosulfonyl, CF3) 'C1-C20 alkyl group with a succinyl group; An aryl-substituted amine group; an amine group substituted with a C1_C20 alkyl group. The structure of a preferred example of the triptycene derivative according to the present embodiment and the manner of forming the same will be described below. However, the scope of the specification should be based on the scope of the following patent, and should not be exemplified by the following examples. limit.

TPTP

Page 12 200907013

Example 1 i 2,6,14-tricarbazolyltriptycene (hereinafter referred to as TCTP)

Take carbazole (3.0 mmole, 0.5016 g) and the starting material 2,6,14-triiodotriptycene (1.0 page 13 200907013 mmole, 0·632 g) and Pd(dba) 2 (0.06 mmole, 0.033 g) in a high pressure tube . P(i-Bu)3 [0.048 mmole, 0.096 g, 3 mL (10%, in Hexane)] and NaOtBu (4.5 mmole, 0.432 g) were added to the glove box and 3 mL of xylene was added as a solvent. Thereafter, the reaction was sealed in a glove box and placed in a 150 C Shi Xi oil pan for 72 hours. After the end, the mixture was returned to room temperature, and the solution was filtered with cerium oxide and diatomaceous earth and filtered with di-methane. The filtrate was collected, and an appropriate amount of activated carbon was added, and the activated carbon was collected by filtration to extract the filtrate to obtain a pale yellow solid. The pale yellow solid was washed with diethyl ether and filtered to give a white solid, compound TCIP, yield 50%. 'H NMR (500MHz, CDC13): 8.14 (t, J=7.5 Hz, 6 Η), 7.73-7.65 (m, 6 Η),

7.46-7.37 (m, 12 Η), 7.33-7.26 (m, 9 Η), 5.71 (s, 1 Η), 5.63 (s, 1 H) ° 13C NMR (125 MHz, CDC13): 146.70, 146.57, 143.76 , 143.62, 140.91, 140.88, 135.15, 135.11, 125.88, 125.19, 125.12, 124.22, 124.15, 12331, 122.66, 122.62, 120.30, 119.96, 109.90, 109.86, 55.69, 53.48. HRMS (FAB+) : Calcd for (C56H35N3): 749.2831 ; found : (to) 749.2829.

Example 2 2,6,14-tris(diphenylamino)triptycene (hereinafter referred to as TPTP)

Take bromobenzene (6.0 mmole, 0.942 g, 0,64 mL) and starting material on page 14 200907013 2,6,14-triaminotriptycene (1.0 mmole, 〇·3 g) and Pd(dba) 2 (〇〇6 mm〇 Le, 〇〇33 g) Place in a high pressure tube. Add P(i_Bu)3 [〇〇48 mm〇le, 〇〇96 g, 3 (1〇%, m Hexane)] and NaOtBu (9.0 mmole, 0.864 g) to the glove box and add 3 mL of xylene. As a solvent. The reaction was then placed in a glove box at 145. The reaction was carried out in a wok pan for 48 hours. After completion, the mixture was returned to room temperature, and the solution was filtered with EtOAc (EtOAc) and EtOAc (EtOAc). The slightly yellow solid was washed with diethyl ether and a white solid, compound TP. *H NMR (500MHz, CDC13): 7.20-7.16 (m, 12 Η), 7.11-6.95 (m, 24 Η), 6.68 (d, J=2 Hz, 1 H), 6.66 (d, J=2.5 Hz , 1 H), 6.64 (d, J=2 Hz, 1 H), 5.09 (s, 1 H), 4.98 (s, 1 H) 〇13C NMR (125 MHz, CDC13): 147.91, 146,72, 144.94 , 144.83, 139.77, 139.22, 129.14, 129.11, 12431, 124.16, 124.06, 123.87, 122.52, 122.46, 120.30, 119.89, 119.63, 119.20, 53.37, 52.78 〇HRMS (EI+) : Calcd for (C56H4iN3): 755.3300 ; found : (1^) 755.3300.

Example 3 2, 5-dimethoxy-3,4-diphenyl-triptycene (hereinafter referred to as TP)

1- phenyl boronic acid (12.3 mmole; 1.5 g) and 2, 5-dimethoxy-3,4-dibromotriptycene (4.1 mmole; 1.9 g) were placed in a high pressure sealed tube, and catalyst Pd(PPh3)4 (5 mole %) was added. ; 0.23 g), a 2M potassium carbonate aqueous solution (2〇mm〇ie; page 15 200907013 2.8 g), dimethoxyethane (DME) 8 mL as a solvent, Suzuki coupling for carbon-carbon bond addition reaction. After the reaction is completed, the dihalomethane is used as the extract, and the organic layer solution is subjected to rapid column chromatography to obtain a yellow clear solution. After removing the water by anhydrous sulfuric acid, the organic solvent is extracted by a cyclone concentrator, and then added to B. The mystery can be washed out as a white solid with a yield of 67 〇/〇. H NMR (400 M Hz, CDC13): <=> 3.38 \s, 6 H), 5.86 (s, 2 H), 6.93-6.96 (m, 4 H), 7.04-7.09 (m, 8 H) , 7.49 (dd, J = 5.2 Hz, J = 3.2 Hz), 7.54 (d, J = 7.2 Hz). 7.47 (dd, J = 2 Hz, 4H). 13C NMR (100 MHz, CDC13): 々48.5\CH), 61.4 (CH3), 123.9 (CH), 125.4 (CH), 126.2 (CH), 127.2 (CH), 130.9 (CH), 133.2 (C), 136.6 (C), 138.4 (C), 145.3 (C), 149.0 (C). MS (EI, m/z): 466.1941 (JvT). Anal. Calcd. for C34H26 〇 2: C, 87.28 %; H, 5.54 %. Found: C, 87.52 %; H, 6.62 %.

Example 4 2, 5-dimethoxy-3,4-di-biphenyl-triptycene (hereinafter referred to as TBP)

The synthesis method of TBP is the same as that of Example 3. It is only necessary to replace the starting material i_phenyl boronic acid with Biphenyl-4-boronic acid. Under the same reaction conditions, the coupling reaction of carbon-carbon bonds is carried out, and the reaction time is different due to steric hindrance. It can be extended to 3-5 days; finally, the solid of TBP can be washed out by methanol, and the yield is about 58°/〇. Page 16 200907013 !H NMR (400 MHz, CDC13): 3.43 (s, 6 H), 5.89 (s, 2 H), 7.06-7.08 (m, 8 H), 7.27 (t, J=7.2 Hz, 2 H), 7.35-7.38 (m, 8 H), 7.49 (dd, J=5.2 Hz, J=3.2 Hz), 7.54 (d, J=7.2 Hz). 13C NMR (100 M Hz, CDC13): 48.6 ( CH), 61.5 (CH3), 123.9 (CH), 125.4 (CH), 125.9 (CH), 126.8 (CH), 127.1 (CH), 128.6 (CH), 131.4 (CH), 132.7 (C), 135.6 ( C), 138.6 (C), 138.7 (C), 140.7 (C), 145.3 (C), 149.2 (C). Fine 1. Calcd. for C46H3402: C, 89.21 %; H, 5.54 %. Found: C, 89.29 %; H, 5.54 %.

Example 5 2, 5-dimethoxy-3,4-di-(4-triphenylsilyl-l-phenyl)-triptycene (hereinafter referred to as TPSi)

The synthesis method of TPSi is the same as that of Example 3 'only need to replace the starting material i_phenyl boronic acid with 4-triphenylsilyl-l-phenylboronicacid. Under the same reaction conditions, the coupling reaction of carbon-carbon bond is carried out, and the reaction time is three-dimensional. The barrier can be extended to 3-5 days; finally, the solid of TPSi can be washed out with methanol in a yield of about 60%. ]H NMR (400 MHz, CDC13): ^ \s, 6 Η), 5.86 (s, 2 Η). 6.97 (d, J=8.4

Hz, 4 H), 7.04 (dd, J=5.2 Hz, J=3.2 Hz, 8 H), 7.19-7.25 (m, 12 H), 7.29-7.36 (m} 10 H), 7.43-7.47 (m, 16 H). 13C NMR (l〇〇M Hz, CDC13): 々48.5 (CH), 61.5 (CH3), 123.9 (CH), 125.4 (CH), 127.8 (CH), 129.5 (CH), 130.5 (CH) ), 131.7 Page 17 200907013 (C), 132.8 (C), 134.2 (C), 135.2 (CH), 136.3 (CH), 137.9 (C), 138.6 (C), 145.2 (C), 149.0 (C) HRMS (FAB, m/z)·· calcd for C5〇H28F24 982.3662, found 983.3732 (M+H^). Anal. Calcd. for C7〇H54〇2: C, 85.09%; H, 5.39%. Found: C, 85.09%; H, 5.54%.

Example 6 2, 5-dimethoxy-3,4-di-[4-(N,N-diphenylamino)-l-phenyl]-triptycene (hereinafter referred to as ΤΡΑ)

The synthesis method of TPA is the same as in Example 3. It is only necessary to replace the starting material 1 _Phenyl boronic acid with 4-(N,N-diphenylamino)-l-phenylboronic acid. Under the same reaction conditions, the carbon-bonding is carried out under the same reaction conditions. In the coupling reaction, the reaction time is extended to 3-5 days due to steric hindrance; finally, the solid of TPA can be washed out by sterol, and the yield is about 65%. W NMR (400 M Hz, CDC13): s, 6 H), 5.86 (s, 2 H), 6.81-6.87 (m, 8 Η), 6.95 (t, J = 7.2 Hz, 4 Η), 7.00-7.05 (m, 8 Η), 7.18 (t, J = 7.2 Hz), 7.46 (dd J = 5.2 Hz, J = 3.2 Hz). 13C NMR (100 M Hz, CDC13): <=> 48.5 (CH) 61 4 (CH3), 122.5 (CH), 122.8 (CH), 123.8 (CH), 124.1 (CH), 125.3 (CH), 129.2 (CH), 131.1 (C), 131.8 (CH), 132.9 (C) , 138.2 (C), 145.3 (C), 145.8 (〇, 147.7 (C), 149.1 (C). Anal. Calcd. for C58H44N202: C, 86.90%; H, 5.52 °/.; N, 3.20 %

Found: C, 86.97 %; H, 5.54 % N, 3.50 %. Page 18 200907013

Example 7 2'5-dimethoxy-3'4-di[4-(9/^carbazol-9-yl)phenyl]-triptycene (hereinafter referred to as TPC)

The synthesis method of TPC is the same as that of Example 3. It is only necessary to replace the starting material i_pheny 〖 b〇r〇nic acid with 4-(9 ugly carbazol-9-yl) phenylboronic acid, under the same reaction conditions, The coupling reaction of the slave bond's reaction time can be extended to 3 to 5 days due to steric hindrance; finally, the solid of TPC can be washed out with methanol in a yield of about 63 〇/〇. 'H NMR (400 MHz, CDC13): 1 \s, 6 Η), 5.96 (s, 2 Η), 7.11 (dd, J= 5.6 Hz, J= 3.2 Hz, 4 H), 7.21-7.23 (m, 8 H), 7.26-7.28 (m, 8 H), 7.39 (d, J= 8 Hz, 4 H), 7.54 (dd, J= 5.6 Hz, J= 3.2 Hz), 8.09-8.11 (m, 4 H 13C NMR (100 M Hz, CDC13): ^ ^CH), 61.7 (CH3), 109.5 (CH), 119.8 (CH), 120.2 (CH), 123.3 (C), 124.0 (CH), 125.5 (CH) ), 125.9 (CH), 126.0 (CH), 132.4 (CH), 132.5 (C), 135.9 (C), 136.0 (C), 139.2 (C), 140.7 (C), 145.1 (〇, 149.1 (〇〇)

Example 8 2,6,14-tris[4-(triphenylsilyl)phenyl]triptycene (hereinafter referred to as TSTP) Page 19 200907013

The starting materials 2,6,14-triiodotriptycene (0.25 mmole, 0.1580 g) and Pd(PPh3)4 (0.0375 mmole, 0.043 g) and 4-(triphenylsilyl)phenylboronic acid (1.25 mmole, 0.4754 g) were placed in a high pressure tube. . Then enter K2C03 aqueous solution (1 mmole, 0.138 g K2C03 dissolved in 0.5 mL H^O) and use 1,2-dimthoxyethane (1 mL) as solvent. After sealing the tube, place it in a simmering pan at 95 °C. The reaction was carried out for 5 days. After the end, the mixture was returned to room temperature, and the solution was filtered over Celite and Celite, washed with dichloromethane, and filtrate was collected, and then TSTP was purified by column chromatography to give a yield of about 65%. JH NMR (400 MHz, CDC13): δ 5.56 (d, J = 4.8 Hz, 2H), 7.23-7.25 (m, 3H) 7.34-7.44 (m, 30H), 7.49 (t, J = 7.2 Hz, 9H) , 7.55-7.57 (m, 21H), 7.65 (m, 3H) 〇

Example 9 2,6,14-tris(diphenylphosphine oxide)triptycene (hereinafter referred to as TP〇TP) Page 20 200907013

The starting materials 2,6,14-triiodotriptycene (0.5 mmole, 0.3160 g) and Pd(OAc)2 (0.003 mmole, 0.010 g) were placed in a high pressure tube. Then add Ηρρ1ΐ2 (2 〇mm〇le. 0.3724 g) to the glove box and remove it from the glove box. Then, add triethylamine and use acetonitrile (CH3cN) (2 mL) as solvent to seal the tube. The reaction was carried out in a frying pan at 85 ° C for 72 hours. After the end, the mixture was returned to room temperature, and the solution was filtered with chlorite and diatomaceous earth and washed with a gas chamber, and the filtrate was collected. Then, 2,6,14-tris was purified by column chromatography. (diphenylphosphine)triptycene, then 2,6,14-tris(diphenylphosphine)triptycene is dissolved in dichloromethane and added to 3〇0/〇H2〇2/° 0, after stirring at room temperature for 24 hours, Extracted with two gas methane several times, the organic layer solution is used as a helmet

The water magnesium sulfate was dehydrated, the filtrate was collected by hydrazine, and the white solid obtained by draining the filtrate was TPOP, and the yield was about 70%. !H NMR (400 MHz, CDC13) : δ 5.48 (d, J=2l.6 Hz, 2H), 7.14 (dd, 1 = 12.4 Hz, J=7.2 Hz, 2H), 7.19-7.26 (m, 3H) , 7.36 (dd, J=7.6 Hz, J=2.4 Hz, 2H), 7.4-7.6 (m 12H), 7.51-7.54 (m, 5H), 7.59-7.65 (m, 12H), 7.72 (d, J= 11.2 Hz, 3H), 7.82 (d J=10.8 Hz, 1H). ’

Example 10 Page 21 200907013

The main physical mass measurements of the triptycene derivatives disclosed in Examples 1 to 2 are summarized in Table 1 below: Table 1 TCTP TPTP λ^8 (nm) 343, 329, 294, 242 310, 227 λ max (ηΠΙ) 410 , 438,460 422,438 λ max (nm) 352 368 triplet state energyd (eV) 3.02 2.94 HOMOe (eV) 6.02 (5.86) 5,66 (5.57) LUMO (eV) 2.40 (2.24) 2.10(2.01) Tmf(°C) 378.1 300.3 Tg8(°C) 237.8 178.4 Tch (°C) XXX 265.5 a. The UV-vis absorption is measured by CH2Cl2 as a solvent, and the solution concentration is about 1χ1〇-5Μ; b. The photoluminescence is measured. Using EtOH as solvent, the 77 kc luminescence intensity measurement system uses CHzCl2 as the solvent' solution concentration is about ix10-5m; d. EtOH is used as solvent at 77 K; e. Redox measurement system is carried out in (3⁄43⁄4, The solution concentration is about 1x10-3m, and the published phase is the value of Cp2Fe/Cp2Fe+; f. Melting point g·glass transition temperature (Glass transition temperature^ h. Crystal-growth temperature Page 22 200907013

Example 11

The main physical properties of the three snails disclosed in Example 3 to Example 7, _, and 碲 bamboo organisms: The results are summarized as shown in Table 2_1 to Table 2-2 below, where ±, 1 is a triptycene derivative TP , photo-physical properties of TBP, TPA, TPSi and TPC, Table 2. 2 thermal properties of the three-strand derivatives Ίηρ, rap, TPA, TPSi and TPC. f" Table 2-1. Xmax Abs.in DCM (nm)a Xmax EM in DCM (nm)b Xmax EM (thin film) (nm)c Xmax EM (77K) (nm)d TP 273 354 350 430 TBP 275 386 378 474 TPA 228; 310 400 392 450 TPSi 228; 242 364; 420 352; 382; 404 442 TPC 237; 294 352; 364 354; 398; 418 412 homo 6.17 5.51 6.13 a. UV-vis absorption measurement solution The concentration is about ιχ10_5μ;

Es 4.05 3.87 3.48 4.05 3.62 Εχ· (eV) 2.88 2.61 2.75 2.80 3.01 b. The concentration of the illuminance measurement is about 1 χ 1 〇·5 μ; c. the thickness is about 300 nm; d. Performed in 2-methyl THF; e. HOMO was measured by ACII versus TBP, cv versus TPA and TPC, respectively; f 200907013 Table 2-2.

TP TBP Tg(°C) 149.1 143.4 248.4

Tm(°C)c TPA TPSi TTC 171.1 184.6 275.1 286.5 340.3 315.2 353.7

The heating rate and the cooling rate are l〇°C/min; b·day-day generation>Crystal-growtli temperature; c. heating rate and cooling rate are 2 (Tc/min. According to the embodiment, The above-mentioned three-butterfly derivative has the advantages of good thermal stability and high triplet energy level difference. Therefore, when the above-mentioned triptycene derivative is applied to an organic electronic component, in addition to high thermal stability, the organic electronic component can be used. In addition to the increase in lifetime, when the above-mentioned tripterene derivative is applied to an organic light-emitting element, it can further complement the existing energy-producing materials which are generally not applied to the main illuminant material and which are common to various types of luminescent materials. For example, the addition of various phosphorescent materials such as blue, green, and red of metal complexes such as iridium (Ir), platinum (Pt), and hungry (Os) to adjust various luminescent layers of practically desired wavelengths. In one embodiment, the above-mentioned triptycene derivative can be used in an organic electroluminescence element and/or a phosphorescence element, in particular, a main illuminant applied to an organic electroluminescence element and/or a phosphor element. Page 24 200907013 material (h〇st material), eiectronic transport material, or h〇ie transport material. In addition, the above-mentioned three-butterfly derivative can also be applied to other organic electronic components ( 〇rganic electronic devices) an electron conducting material (electr〇nic transp〇rt material), a hole conducting material (h〇le transp〇rt mateHal). The above organic electronic components may be organic solar cells, organic thin film transistors, organic A photoconductor, or other organic semiconductor component known to those skilled in the art. According to a second embodiment of the present invention, an organic light emitting device is disclosed. In general, the color of the organic light emitting device is mainly determined by the fact that the component has a fluorescent element. Organic material of optical characteristics' Therefore, the organic light-emitting element can improve the recombination efficiency of the carrier by mixing a small amount of high luminous efficiency guest in the main illuminator (h〇st), which has a ratio of main illuminating Small energy gap, high luminous efficiency, and shorter recombination lifetime than the main illuminator, so The exciton of the main illuminant is transferred to the guest illuminant by the process of energy transfer for rapid and efficient recombination. In addition to improving the efficiency of luminescence, the illuminating color can be traversed throughout. The visible light region is often used together with the main illuminant by co-evaporation (co_evap〇rati〇n) or dispersion, and is energy transfer or carrier trap. The mode accepts energy from the excited main illuminator, resulting in the generation of different colors (red, green, blue) and enhancing the luminous efficiency of the element. In addition to the above-mentioned Fluorescence guest illuminants, new developments have been made in the study of Phosphorescence. When the organic molecules are excited, there will be a single-single state of the asymmetric electrons in the excited phase of 200907013 1/4 on page 25, and the energy will be released by fluorescence, but there will be 3/4 of the excited electrons. The triplet state of the symmetric spin is formed, and the energy is released by the non-radioactive light structure, which greatly loses the efficiency and reduces the luminous efficiency. At present, materials capable of emitting phosphoric light in the triplet state of excimer electrons are organometallic compounds, and the central metals are transition metals such as osmium (Os), lanthanum (rr), platinum (Pt), lanthanum. (Eu), ruthenium (Ru), etc., and the ligand thereof is a heterocyclic compound containing nitrogen. According to this embodiment, the above organic light-emitting element includes a pair of electrodes and at least one organic layer between the electrodes. Wherein at least the organic layer comprises a light-emitting layer, and at least one of the organic layers comprises a triptycene derivative, and the general structure of the above-mentioned triptycene derivative structure is as follows: R6

--- 'One of the wilderness: an aromatic group having one or more substituents; an aromatic heterocyclic group having one or more substituents; a non-aromatic cyclic group having one or more substituents group;

R13, R14 R15 -Ν' R16

R19

Si ~ r2〇

200907013 ΟII G—ρ- R13 R15 —Bu G—B〆 十 G—N \R14 . , R16 , The above substituent may be one selected from the group consisting of a hydrogen atom and a dentate atom (for example, fluorine, Gas, bromine, iodine); aryl, halogen-substituted aryl, halogen-substituted arylalkyl, dentate-substituted aryl, alkyl-substituted arylalkyl, aryl-substituted C1-C20 alkyl; Electron donating group ' such as C1-C20, C1-C20 cycloalkyl (eg methyl, ethyl, butyl, cyclohexyl), C1-C20 alkoxy group, C1 a -C20 substituted amino group, a substituted aromatic amine group [e.g., an aniline], or an electron withdrawing group such as a halogen, a nitrite, a nitrile, a nitrate A nitro group, a carbonyl group, a cyano group, and a halogen-substituted c1-C20 alkyl group (e.g., a trifluoromethyl group, CF3); a heterocyclic substituent group. The above G may be one selected from the group consisting of an aromatic group having one or more substituents; an aromatic heterocyclic group having one or more substituents; and a heterocyclic ring having one or more substituents. Group. The substituent of the above G may be one selected from the group consisting of a hydrogen atom, a halogen atom (for example, fluorine, gas, bromine, or mechanical); an aromatic group, a halogen-substituted aromatic group, a dentate-substituted aromatic alkyl group, Adentate-substituted aryl, alkyl-substituted aromatic alkyl, aryl-substituted C1-C20 alkyl; electron donating group, such as C1-C20 alkyl, C1-C20 cycloalkyl ( For example: methyl, ethyl, butyl, cyclohexyl), C1-C20 alkoxy group, C1-C20 substituted amino group, substituted aromatic amine group [eg anilino group ( Aniline)], or electron withdrawing group

-R

R 17 18 R19 R20 , \ R21 Page 27 200907013 For example, halogen, nitrile, nitro, carbonyl, cyano (-CN) and halogen-substituted C1-C20 alkyl (e.g., trifluoromethyl, CF3); a heterocyclic substituent. R13 to R21 may be the same or different, and Ri3 to R21 are independently selected from one of the following groups: a hydrogen atom; a C1-C20 alkyl group, a C1-C20 cycloalkyl group (e.g., methyl, ethyl, butyl). a group, a cyclohexyl group; a Cl-C20 alkoxy group; an amino group; an aromatic group having one or more substituents; an aromatic heterocyclic group having one or more substituents. The above substituents of R13 to R21 are independently selected from one of the following groups: a hydrogen atom, a halogen atom, an aromatic group, a halogen-substituted aromatic group, a halogen-substituted aromatic alkyl group, a haloalkyl-substituted aromatic group, a halogenated alkane. Alkyl-substituted arylalkyl group, aryl-substituted C1-C20 alkyl group, C1-C20 alkyl group, C1-C20 cycloalkyl group, C1-C20 alkoxy group, C1-C20 substituted amine group (amino Group), an aromatic amine group having a substituent, or a C1-C20 alkyl group substituted with an electron withdrawing group, a halogen-substituted C1-C20 alkyl group (for example, a trifluoromethyl group, CF3), or a hetero group The ring substituent group is either a nitriie group, a nitro group, a carbonyl group, or an EYano group (CN). Further, it is to be noted that, in the triptycene derivative structure according to the present embodiment, R1 to R12 may not be hydrogen atoms at the same time. According to this embodiment, the above aromatic group may be selected from the group consisting of phenyl, naphthyl, diphenyl, anthryl, pyrenyi, phenanthryl. And a benzoene or other form of polyphenyl ring substituent. The above aromatic heterocyclic group may be selected from the group consisting of α-pyrane, pyii*〇iine, fUran, benzofiiran, thiophene, benzo. Benz〇thiophene, page 28 200907013 D pyridine, ^. (quinoline), isoquinoline, pyrazine, pyrimidine, ° ratio 11 ( Pyrrole), pyrazine (pyraz〇ie), imidazole, indole, thiazole, isothiazole, oxazole, isoxazole ), benzothiazole, benzoxazole, 1,2,4-trioxalysis. Sitting (l,2,4-triazole), 1,2,3-three-degree sputum (1,2,3-out 〇2: 〇卜), 1,2,3,4-four 恶 唾 (^ Coffee 2〇16), and - phenanthroline' or other forms of heteronuclear aromatic rings. The above non-aromatic ring group may be one selected from the group consisting of: a hydrogen atom, a _ atom (for example, fluorine, chlorine, bromine, iodine); a C1-C20 alkyl group, a C1-C20 cycloalkyl group; (eg methyl, ethyl, butyl, cyclohexyl); C1-C20 alkoxy (aik〇Xy group); amino group; nitrile group; nitro (nitr〇 group) a carbonyl group; a cyano group ( _CN); an aryl group; a halogen-substituted aryl group; a C1-C20 haloalkyl-substituted aryl group; a C1-C20 haloalkyl group-substituted aryl group; An aryl-substituted C1-C20 alkyl group; an amine group substituted with an aryl group; an amine group substituted with a C1-C20 alkyl group; an aromatic amine group having a substituent. .4 The general procedure for the formation of organic light-emitting elements is to take the ITO glass with the circuit diagram of the last name, add neutral detergent: deionized water: 5 〇 cleaning solution, placed in the ultrasonic oscillator for 5 minutes, then with soft hair Brush and wash the glass, then place the glass in 50 mL of deionized water and electronic grade acetone for 5 minutes, then blow dry with nitrogen. Place the cleaned ITO glass in the UV-Ozone machine for 5 minutes. After removal, fix it on the substrate (face down) and put it into the steamer to vacuum until the vacuum of the chamber reaches 5χ1. The step of vapor-depositing the film can be performed only by 〇·^ογγ. The conditions of the vapor deposited film are organic plating, page 29, 200907013. The film rate is controlled between 1 and 2 A/s, and the desired organic film is sequentially vapor-deposited, and the rate of metal plating is 5 A/s, silver is 0.5 Λ / s 'Magnesium: Silver = 1 〇: The thickness of the metal film deposited by magnesium and silver is 55 nm. Finally, a layer of 1 〇〇 nm of silver is plated as a protective layer. If the metal is selected for the fluorination clock/sauer system, it must first be fluorinated at a rate of 0.1 A/s, and the film thickness is controlled to be 1 Å. • Then a layer of l〇〇nm aluminum is applied as a protective layer. . During the coating process, the rotation rate of the component is 20 rpm, and after the vapor deposition is finished, it is necessary to wait for 20 minutes for the metal electrode to cool down, so that the cavity can be returned to the atmospheric pressure to return to normal pressure. On the other hand, after the preparation of the OLED device, the electro-spectral fluorescence spectrum (EL spectra) and the CIE coordinate diagram (CIE coordination) of the Hitach measurement component are obtained by the F-4500, and further, by the Keithley 2400 programmable voltage-current source. Measuring the current, voltage and brightness of the component. The above measuring instruments are operated at room temperature under atmospheric pressure (about 25. (:).

Example 12 By the above-described general procedure for forming an organic light-emitting element, a TCTP-based illuminant material is respectively doped with a blue phosphorescent material to form an OLED element, and the aforementioned doped blue phosphorescent material is as follows: Page 30 200907013

F F

F F

The individual components of the above components are structured as follows: Component 3A: NPB (30) / TCTP: FIrpic (7%) (30) / BCP (15) / Alq (30) Component 3B: NPB (30) / mcp (20) / TCTP : FIrpic (7%) (30) / BCP (15) / Alq (30) Component 3C: TCTA (30) / mcp (20) / TCTP: FIrpic (7%) (30) / BCP (15) / Alq ( 30) Element 3D: NPB (30) / mcp (20) / TCTP: FIrpic (6.3%) (30) / TPBI (30) wherein the cathodes of the above elements 3A to 3D are Li (1) / A1 (100), The thickness of the components is in nm. The optical properties and efficiency measurement results of components 3A to 3D are shown in Table 3-1 below. Table 3-1: Element VI Lumb textc fcd tpe piece (V) (cd/m2) (%) cd/A (Im/W) (%) 3A 4.6 37992@14.5V 5.8@10.0V 12.2@10.0V 4.1@ 9.0V 0.14, 0.34@8v 3B 4.6 46739@16.0V 10.1@6.5V 21.9@6.5V 12.4@5.0V 0.14,0.36@8v 3C 5.6 37385@18.0V 6.4@11.5V 13.8@11.5V 4.0@10.0V 0.14, 0.35@8v 3D 5.1 17692@13.0V 4.9@9.0V 8.8@9.0V 3.2@8.0V 0.13,0.28@8v Page 31 200907013 Component 3E: NPB(30)/mcp(20)/TCTP: (<1φργ) 2Ιτ(ργΙζ) (7%Χ30)/ΤΡΒΙ(30) Element 3F: NPB(30)/mcp(20)/TCTP:FIrN4(7%)(30)/BCP(15)/Alq(30) Component 3G: ΝΡΒ (25) / πκ; ρ (25) / Τ σ ΓΡ: ΡΙ η ^ φ (7.7%) (30) / BCP (15) / Alq (30) wherein the cathode of the above elements 3E ~ 3G is Li (l) / Al (100) The measurement results of the optical properties and efficiency of the elements 3E to 3G in the thickness units of the above elements are shown in Table 3-2 below. Table 3-2:

Component V/ Lumb (%) (V) (cd/m2) 3E 5.0 16777@13.5V 3F 5.4 7777@ 16.0V 3G 7.0 15462@17.5V text (%)

T〇d cd/A tpe (Im/W)

C.I.E

5V

5V

Example 13 According to the general flow of forming the organic light-emitting element described above, the TPTP is used as the main light-emitting material, and the guest light-emitting material is respectively connected to form an OLED element. The doped guest light-emitting material is as follows:

F

FIrpic Ir(ppy)3

Ir(DBQ)2(acac) Page 32 200907013 The individual components of the above components are structured as follows: Component 3H: NPB (40) /TPTP: FIrpic (7%) (30) / BCP (15) / Alq (30) Component 31 : NPB(30)/mcp(20)/ TPTP: FIrpic(6.7Q/〇)(30) /BCP(15)/Alq(30) Component 3J: TCTA(30)/mcp(20)/ TPTP: FIrpic( 6.7%) (30) / BCP (15) / Alq (30) Element 3K: NPB (30) / mcp (20) / TPTP: FIrpic (6.7%) (30) / TPBI (30) where the above element 3H~ The cathode of 3K is Li(l)/Al(100) 'The thickness of each of the aforementioned elements is nm. The optical properties and efficiency measurement results of the components 3H to 3K are shown in Table 3-3 below. Table 3-3: Component (%) vf Lumb fextc t〇d tPe CIE (V) (cd/m2) (%) cd/A (Im/W) 3H 3.1 5625@11.0V 0.6@6.0V 1.2@4.5V 1_2@3.0V — 〇.14,0.30@8v 31 4.7 32313@14.0V 7.8@7.0V 16.7@7.0V 8.2@6.0V 〇.14,0.35@8v 3J 6.6 28618@19.5V 8.1@7.5V 17.3@7.5 V 7.2@7.5V 〇.14,0.35@8v 3K ------ 4.7 17266@13.0V 7.6@7.0V 14.0@7.0V 6.8@6.0V 〇13,0.29@8v TPTP-based illuminant material, The structure of the OLED device formed by doping the green scale material Ir(ppy)3 is as follows: Element 3L·NPB(30)/mcp(20)/TPTP: Ir(ppy)3 C7.3%X3〇yBCP(15yAIq(30) Element 3M: TCTA (30) / mcp (20) / TPTP: Ir (ppy) 3 (6.8%) (30) / BCP (15) / Alq (30) wherein the cathodes of the above elements 3L and 3M are Li ( 1) / A1 (100), the thickness of the aforementioned elements are all in nm. The optical properties and efficiency measurement results of the elements 3L and 3M are shown in Table 3-4 below. Page 33 200907013

Table 3-4 fcd cd/A tPe (im/W)

CIE component K/a Lumb fextc (%) (V) (cd/m2) (%) 3L 4.2 58930@16.0V 7.2@11.0V 26.1@ll.〇V 7·9@1〇·〇ν 〇·24, 0.64@8ν 3M 4.3 41054@13.5V 11.5@8.0V 41.2@8.〇V II is a tptp-based illuminant material, and the OLED element structure formed by doping red phosphorescent material Ir(DBQ)2(acac) is as follows: 3N: TCTA(30)/ mcp(20)/ TPTP: Ir(DBQ)2(acac)(7%)(30)/ BCP(10)/ Alq(40) Component 30: TCTA(30)/mep(20 ) /TPTP: Ir(DBQ) 2 (acac) (10%) (30) / BCP (15) / Alq (30) Element 3P: NPB (30) / mcp (20) / TPTP: Ir (DBQ) 2 ( Acac) (10%) (30) / BCP (15) / Alq (30) Component 3Q: NPB (30) / mcp (20) / TPTP: Ir-red (10%) (30) / BCP (15) / Alq(3〇) wherein, the above-mentioned tl pieces 3N to 3Q of the cathode $Li(l)/Al(l〇〇), the thickness of the above elements are all in nm. The optical properties and efficiency measurement results of the elements 3N to 3Q are shown in Table 3-5 below. Table 3-5 Components in (%) (V)

Lumb (cd/m2) C ’ext(%)

Tcd cd/A

Tpe(Im/W)

CIE y 44@说3·8@ια5ν 8.3@ig.57^t^7 30 4.i face@14.0V 3.6@1 with ^Chang 24@9〇v 〇6i 〇3P 4,3 Na to take 5.5V 9,8@6.5V 19 Green 5V 9 4@5 w 〇62 〇38@8v Page 34 200907013

Example 14 According to the general flow of forming the organic light-emitting element, the three-butterfly derivatives IBP, TPA, TPSi and TPC are used as the main light-emitting materials, and the guest light-emitting materials are respectively doped to form an OLED element, and the individual element structures of the above elements are As follows: Component TBP1: NPB (30) / TCTA (20) / TBP: FIrpic (6%) (30) / BCP (10) / Alq (30) Component TPA6: NPB (30) / mCP (20) / TPA: FIrpic (6%) (30) / BCP (10) / Alq (30) Element TPA8: NPB (30) / mCP (20) / TPA: Ir (ppy) 3 (6%) (30) / TPBI (30) Element TPSi3: NPB (30) / TCTA (20) / TPSi: FIrpic (6%) (30) / BCP (10) / Alq (30) Component TPC2: TPD (30) / mCP (2 〇 yTPC: FIrpic (6) %X30)/BCP(15yAlq(30) where 'the cathode of each of the above elements is Li(l)/Al(100)' The thickness of each of the above elements is (10). The optical properties and efficiency measurements of the above components are as follows: 3-6. Table 3-6 Component V/ (V) Lumb (cd/m2) Hextc (%) _ d He (cd/A) nPe (Im/W) CIE' TBP1 6.8 7235 2.4@11.5V 5.3 @11.5V 1_7@9V (0.14,0.34) TPA6 4.6 13473 4.4@6.5V 9.7@6.5V 5@5.5V (0.14,0.35) TPA8 4.7 31533 8.8@7V 31.5@7V 18.7@5V (0.22,0.64) TPSi3 4.5 8442 5.0@5V 10.5@5V 6.6@5V (0.15,0.33) T PC2 4.5 13729 3.8^6.5 V 7.8__5V 4.3(%5Y (0.14,0.32) a. Drive voltage (» b. Luminescence {Luai) > c. Maximum external quantum efficency iVexb ' d. Maximum current efficiency (η〇) ' e. Maximum power efficiency (ηρ) > i CIEx, y at In the present embodiment, the above-mentioned triptycene derivative structure can be used for the host material (host) of organic light on page 35 200907013 electroluminescence element. Material), a single layer of luminescent material, an electronic transport material, or a hole transport material. On the other hand, the above-mentioned tripterene derivative has the characteristics of electron conduction and hole conduction, and therefore can be applied to an organic electroluminescence element or even an electron conduction or hole conduction material of other organic electronic components. According to the present specification, since the above-mentioned triptycene derivative has an advantage of high thermal stability, when the above-mentioned triptycene derivative is applied to an organic electronic component, the service life of the organic electronic component can be effectively extended. The other side ^ Due to the high triplet energy level difference of the above-mentioned bis-cepene derivatives, when the above two (J^·) derivatives are applied to organic light-emitting elements, they can be further complemented by blue, green, and Red, and other materials in the main layer of various counties can't reach the mystery', and the general-purpose materials such as iridium (Ir), platinum (Pt), and hungry (OS) are in conformity with materials. For example, the benefits of the monument and the utility of the industry. Obviously, the invention may have many modifications and differences in accordance with the description in the above system. Therefore, it is to be understood that within the scope of the appended claims, the invention may be The above is only the preferred system of the present invention, and is not intended to limit the scope of the present invention; any other changes or modifications that are not to be made in the spirit of the present invention should be included in the following claims. Inside. > Page 36 200907013 [Simplified illustration] [Main component symbol description]

Claims (1)

200907013 X. Patent application scope: 1. A triptycene derivative. The general structure of the triptycene derivative is as follows: R6 R3 wherein R~R may be the same or different, and R1 to rU are independently selected from one of the following groups: an aromatic group having one or more substituents, and an aromatic heterocyclic group having one or more substituents. a non-aromatic ring group having one or more substituents, c /Rl3 s R15 Ο -卜Β -1-Ν, 丨丨-卜Ρ· -RR R16 R18 R19 -Bu Si-R20, R21 1 R 13 G—BR 14 — 卜: R15 O R16 R R19 G—Si—R20 N〇2i wherein the above G may be one selected from the group consisting of an aromatic group having one or more substituents, An aromatic heterocyclic group having one or more substituents, a heterocyclic group having one or more substituents; the above substituents are independently selected from one of the following groups: a hydrogen atom, a halogen atom, an aromatic group , halogen-substituted aromatic group, halogen-substituted aromatic alkyl group, functional group-substituted aromatic group, halogen-substituted aromatic group, aryl-substituted C1-C20 alkyl group, C1-C20 alkyl group, C1-C20 a cycloalkyl group, a C1-C20 alkoxy group, a C1-C20 substituted amine group (^ηΰηο group), a fragrant having a substituent Page 38 200907013 Amino, or a C1-C20 leukoxyl, heterocyclic substituent group substituted with an electr〇n withdrawing group; the above R!1~R2丨 may be the same or different, and Rl1 〜R2〗 is independently selected from one of the following groups: a hydrogen atom, a C1-C20 alkyl group, a C1-C20 decyl group, a C1-C20 aikoxy group, an amino group, An aromatic group having one or more substituents, an aromatic heterocyclic group having one or more substituents; the substituent of the above R13 to R2! is independently selected from one of the following groups: a hydrogen atom, a halogen atom, Aromatic group, halogen-substituted aromatic group, halogen-substituted aromatic alkyl group, haloalkyl-substituted aryl group, _alkyl-substituted arylalkyl group, aryl-substituted C1-C20 alkyl group, C1-C20 alkyl group, C1 -C20 cycloalkyl, C1-C20 alkoxy group, C1-C20 substituted amino group (amino gr0Up), substituted aromatic amine group, or electron withdrawing group substituted C1-C20 alkyl, halogen-substituted C1-C20 alkyl (eg, trifluoroalkyl, CF3), heterocyclic substituent Is a nitrite group (nitrile group), Danxiao Ji (nitro group); a few group (carbonyl group); a cyano group (cyano group, -CN); R1~R12 of the above are not simultaneously hydrogen atoms. 2. The triptycene derivative according to claim 1, wherein the above aromatic group comprises one of the following groups: phenyl, naphthyl, diphenyl, Anthryl, pyrenyi, phenanthryl, fluorene' or other forms of polyphenylene ring groups. 1 The triptycene derivative according to claim 1, wherein the above aromatic heterocyclic group comprises one of the following groups: pyran, pyrroline, and pyran 39 pages 200907013 (fUran), benzopyrene (benz〇fi«*an), thiophene, benzothiophene, pyridine, quinoline, iso 0i: Isoquinoline, pyrazine, pyrimidine, pyrrole, pyrazole, imidazole, indole, indole (thiazole), isothiazole, oxazole, isoxazole, benzothiazole, benzothiazole, benzoxazole 'l, 2, 4-^.°£°^.(l,2,4-triazole) ' 1,2,3-^-2,3-triazole) ' 1,2,3,4-four°Evil" sitting (^ melon 32〇16), phenanthroline & 11611311 (〇1丨116), or other forms of heteronuclear aromatic ring groups. 4. The triptycene derivative according to claim 1, wherein the non-aromatic ring group may be one selected from the group consisting of a hydrogen atom, a halogen atom, and a C1-C20 alkyl group. , C1-C20 cycloalkyl, C1-C20 alkoxy (alk〇xy group), amino group, nitrile group, nitro group, carbonyl group , cyano group (CN), i-substituted C1-C20 alkyl, aryl-substituted C1-C20 alkyl, aryl-substituted amine, C1-C20 alkyl-substituted amine . 5. The triptycene derivative according to claim 1, wherein the above-mentioned tripterene derivative is used in an organic electroluminescence element and/or a phosphorescence element. 6. The triptycene derivative according to claim 1, wherein the above-mentioned triptycene, page 40, 200907013, is applied to the organic electroluminescent device and the main illuminant material in the phosphor element ( Host material) or a single layer of light emitter (emitter). 7. The triple butterfly derivative according to claim 1, wherein the above-mentioned three butterfly derivative is applied to an electron conductive material in an organic electronic component. 8. The method according to claim 1, wherein the above-mentioned three-butterfly derivative is applied to a hole conducting material in an organic electronic component. 9. An organic hair piece comprising: a counter electrode and at least an organic layer between the electrodes, wherein the at least - the organic layer comprises a light emitting layer, and at least one of the organic layers comprises - a triple butterfly The general structure of the triptycene derivative is as follows: R6 R3 R1 wherein 'R1 to R12' may be the same or different, and Ri to Ru are independently selected from one of the following groups: an aromatic group having one or more substituents, and an aromatic heterocyclic group having one or more substituents. A non-aromatic ring group having one or more substituents, page 41 200907013 ί-Β G_B R13 R15 / \ 十 N R14 , s \ R16 R13 R15 / S / \ \ G-N R14, R16 O O II r17 -G—P^K R19 • l-Si’-R20 R21 · R19 Wherein G may be one selected from the group consisting of an aromatic group having one or more substituents, an aromatic heterocyclic group having one or more substituents, and one or more substituents. a heterocyclic group; the above substituents are independently selected from one of the following group r: a hydrogen atom, a halogen atom, an aromatic group, a halogen-substituted aromatic group, a halogen-substituted aromatic alkyl group, an alkyl-substituted aromatic group. Haloalkyl substituted arylalkyl, aryl substituted C1-C20 alkyl, C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkoxy group, C1-C20 substituted amine An amino group, an aromatic amine group having a substituent, or a C1-C20 alkyl group or a heterocyclic substituent group substituted with an electron withdrawing group; wherein the above R13 to R21 may be the same or different And R13 to R21 are independently selected from one of the following groups: a hydrogen atom, a C1-C20 alkyl group, C1-C20 cycloalkyl, C1-C20 alkoxy group, amino group, aromatic group having one or more substituents, aromatic heterocyclic group having one or more substituents The above substituents of R13 to R21 are independently selected from one of the following groups: a hydrogen atom, a halogen atom, an aromatic group, a halogen-substituted aromatic group, a halogen-substituted aromatic alkyl group, an i-alkyl-substituted aromatic group, i Alkyl-substituted arylalkyl, aryl-substituted C1-C20 alkyl, C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkoxy group, C1-C20 substituted amine group ( Amino group), an aromatic amine group having a substituent, or a pept. # 200907013 is a C1-C20 alkyl group substituted with an electron withdrawing group, a halogen-substituted C1-C20 alkyl group (for example, a trifluoromethyl group). , CF3), a heterocyclic substituent group or a nitrile group, a nitro group; a carbonyl group; a cyano group (-CN); the above R1 to R12 are not hydrogen at the same time atom. 10. The organic light-emitting device according to claim 9, wherein the above aromatic group comprises one of the following groups: phenyl, naphthyl, diphenyl, fluorenyl. (anthryl), pyrenyl, phenanthryl, fluorene, or other forms of polyphenylene ring groups. The organic light-emitting device of claim 9, wherein the aromatic heterocyclic group comprises one of the following groups: pyrane, slightly 11 pyrroline, Fiiran), benzofiiran, thiophene, benzothiophene, pyridine 'quinoline', isoquinoline, pyrazine, pyrimidine Pyrimidine, pyrrole, pyrazole, imidazole, indole, thiazole, isothiazole, oxazole, Isoxazole, benzothiazole, and benzophenone. Benzoxazole, 1,2,4-triazole, 1,2,3-triazole, 1,2,3,4-tetra Tetraazole, phenanthroline, or other forms of heteronuclear aromatic ring groups. 12. The organic light-emitting device according to claim 9, wherein the above-mentioned non-aromatic 43 page 200907013 aromatic ring group may be one selected from the group consisting of hydrogen atoms, halogen atoms, C1- C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkoxy group, amino group, nitrile group, nitro group, carbonyl group , cyano groUp (-CN), halogen-substituted C1-C20 alkyl group, aryl-substituted C1_C20 alkyl group, aryl-substituted amine group, and C1-C20 alkyl group-substituted amine group. 13. The organic light-emitting device according to claim 9, wherein the above-mentioned tripteric derivative is applied to an emitter iayer of the organic light-emitting device. 14. The organic light-emitting device according to claim 9, wherein the triptycene derivative is one of the host materials of the light-emitting layer of the organic light-emitting device. The organic light-emitting device according to the item 9, wherein the above-mentioned triptycene derivative is applied to an electron conductive material of the organic light-emitting element. 16. The organic light-emitting device according to claim 9, wherein the above-mentioned tripterene derivative is applied to a hole conducting material of the organic light-emitting element. 17. The organic light-emitting device of claim 16, wherein the light-emitting layer further comprises a guest emitter material, and the guest emitter material comprises a transition metal complex. 18. The organic light-emitting device of claim 17, wherein the transition metal of the transition metal complex is selected from one of the group consisting of: Ir, platinum, Os. Equal heavy metal elements. The organic light-emitting element of claim 17, wherein the guest light-emitting material is a blue phosphorescent material. 20. The organic light-emitting device of claim 17, wherein the guest emitter material is a red phosphorescent material. 21. The organic light-emitting device of claim 17, wherein the guest emitter material is a green phosphorescent material. 22. The OLED device of claim 9, wherein the luminescent layer (single layer luminescence or as a host material) or a hole conducting material or an electron conducting material comprises a compound having the following The structural formulas TCTP, TPTP, TSTP, TPOTP, TP, TBP, TPSi, TPA, TPC represent: Page 45 200907013 TPC第46页