92638-81-8 (10H-螺[吖-9,9&#x27;-芴],10H-Spiro[acridine-9,9&#x27;-fluorene])

参考文献：

Aromatic heterocyclic delayed fluorescent compound and application in organic light-emitting diode device

, China, , ,

合成路线：1 步

2231404-50-3

_90%

反应条件：

1.1 Reagents: Methanesulfonic acid Solvents: Chloroform ; 30 min, rt; > 24 h, reflux

参考文献：

Organic compound, and organic light emitting diode and organic light emitting display device including the same

, United States, , ,

合成路线：1 步

_89%

反应条件：

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ; -78 °C; 1 h, -78 °C
1.2 Solvents: Tetrahydrofuran ; -78 °C
1.3 Reagents: Acetic acid , Hydrochloric acid

参考文献：

Condensed cyclic compound and organic light-emitting device including the same

, United States, , ,

合成路线：1 步

2231404-50-3

_88%

反应条件：

1.1 Reagents: Hydrochloric acid Solvents: Acetic acid , Water ; 3 h, 60 - 80 °C

参考文献：

Preparation of spiro-acridine derivatives for organic electronic element

, Korea, , ,

合成路线：1 步

_78%

反应条件：

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ; -78 °C; 1 h, -78 °C
1.2 Reagents: Hydrochloric acid Solvents: Acetic acid , Tetrahydrofuran

参考文献：

Organic compound, organic light emitting diode and organic light emitting device having the compound

, United States, , ,

合成路线：1 步

88284-48-4

10183-82-1

_75%

反应条件：

1.1 Reagents: Potassium fluoride , 18-Crown-6 Solvents: Acetonitrile ; 24 h, 81 °C

参考文献：

Synthesis of Benzo[b]fluoranthenes and Spiroacridines from Fluorene-Derived Alkenes and N-Arylimines via a Tandem Reaction with Benzynes

Wang, Weihua; Wan, Hongwei; Du, Guangfen; Dai, Bin ; He, Lin, Organic Letters, 2019, 21(10), 3496-3500

合成路线：1 步

_75%

反应条件：

1.1 Reagents: Triethylamine Solvents: Chloroform ; 3.5 h, rt
1.2 Reagents: Sodium hydroxide Solvents: Water
1.3 Reagents: Potassium fluoride , 18-Crown-6 Solvents: Acetonitrile ; 24 h, 82 °C

参考文献：

Method for preparing 10H-spiro[acridine-9,9'-fluorene] and its derivatives using imine compound

, China, , ,

合成路线：1 步

_70%

反应条件：

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ; -78 °C; 1 h, -78 °C
1.2 -78 °C; 12 h, -78 °C; -78 °C → rt
1.3 Reagents: Methanesulfonic acid ; 1 h, reflux; reflux → rt
1.4 Reagents: Water

参考文献：

Organic compound, and application and organic electroluminescence device thereof

, China, , ,

合成路线：1 步

_70%

反应条件：

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ; 12 h, -78 °C; -78 °C → rt
1.2 Reagents: Methanesulfonic acid ; reflux
1.3 Reagents: Water

参考文献：

Preparation of boracyclic compounds for organic light-emitting element

, World Intellectual Property Organization, , ,

合成路线：1 步

122-39-4

_64%

反应条件：

1.1 Catalysts: p-Toluenesulfonic acid ; 15 min, 150 °C
1.2 0.5 h, 150 °C → 200 °C

参考文献：

Versatile Direct Cyclization Constructs Spiro-acridan Derivatives for Highly Efficient TADF emitters

Liu, He; Liu, Zhiwen; Li, Ganggang; Huang, Huaina; Zhou, Changjiang; et al, Angewandte Chemie, 2021, 60(22), 12376-12380

合成路线：1 步

122-39-4

_62%

反应条件：

1.1 Catalysts: p-Toluenesulfonic acid ; rt → 140 °C; 15 min, 140 °C
1.2 140 °C → 200 °C; 30 min, 200 °C

参考文献：

Preparation of substituted spiro acridine derivatives as OLED materials

, China, , ,

合成路线：1 步

_58%

反应条件：

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; -78 °C; 2 h, -78 °C
1.2 Solvents: Diethyl ether ; -78 °C; 5 h, -78 °C
1.3 Reagents: Sodium chloride Solvents: Water
1.4 Catalysts: Hydrochloric acid Solvents: Acetic acid ; 90 °C; 8 h, 90 °C → 117 °C

参考文献：

Intramolecular Hydrogen-bonding in Thermally Activated Delayed Fluorescence Emitters: Is There Evidence Beyond Reasonable Doubt?

Hempe, Matthias; Kukhta, Nadzeya A. ; Danos, Andrew ; Batsanov, Andrei S. ; Monkman, Andrew P. ; et al, Journal of Physical Chemistry Letters, 2022, 13(35), 8221-8227

合成路线：1 步

_55%

反应条件：

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ; -78 °C; 2 h, -78 °C
1.2 -78 °C; overnight, -78 °C → rt
1.3 Reagents: Methanesulfonic acid Solvents: Chloroform ; 10 h, reflux

参考文献：

Preparation of polycyclic aromatic compounds for organic electroluminescent devices

, China, , ,

合成路线：1 步

_51%

反应条件：

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ; -78 °C
1.2 30 min, -78 °C; -78 °C → rt; overnight, rt
1.3 Reagents: Water
1.4 Reagents: Methanesulfonic acid Solvents: Chloroform ; 10 h, reflux; reflux → rt
1.5 Reagents: Sodium bicarbonate Solvents: Water ; 20 min, rt

参考文献：

Highly efficient blue organic light-emitting diodes from pyrimidine-based thermally activated delayed fluorescence emitters

Li, Bowen; Li, Zhiyi; Hu, Taiping; Zhang, Yong; Wang, Ying; et al, Journal of Materials Chemistry C: Materials for Optical and Electronic Devices, 2018, 6(9), 2351-2359

合成路线：1 步

_43%

反应条件：

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; -78 °C; 4 h, -78 °C
1.2 30 min, -78 °C; 12 h, rt
1.3 Solvents: Water ; cooled

参考文献：

Controllable construction of red thermally activated delayed fluorescence molecules based on a spiro-acridine donor

Liu, Huanling; Zhang, Kai; Zou, Haipei; Mu, Qingfang; Song, Yuzhi; et al, Physical Chemistry Chemical Physics, 2023, 25(2), 1032-1044

合成路线：1 步

_41%

反应条件：

1.1 Solvents: Tetrahydrofuran , Hexane ; -78 °C; 1 h, -78 °C
1.2 3 h, rt
1.3 Reagents: Water
1.4 Catalysts: Methanesulfonic acid Solvents: Chloroform ; 2 h, reflux

参考文献：

Organic compound, and organic light-emitting display panel and organic light-emitting display device

, China, , ,

合成路线：1 步

_41%

反应条件：

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 50 min, 0 °C
1.2 Reagents: Water ; rt
1.3 Reagents: Methanesulfonic acid Solvents: Chloroform ; 3 h, reflux

参考文献：

Luminescent materials having specific substituted heteraborin ring structures, delayed fluorescent materials, organic light emitting devices using them, and compounds for them

, World Intellectual Property Organization, , ,

合成路线：1 步

_41%

反应条件：

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; -78 °C; 1 h, -78 °C
1.2 3 h, -78 °C → rt
1.3 Reagents: Water ; rt
1.4 Reagents: Methanesulfonic acid Solvents: Chloroform ; 2 h, reflux

参考文献：

High efficiency pure blue thermally activated delayed fluorescence molecules having 10H-phenoxaborin and acridan units

Numata, Masaki; Yasuda, Takuma; Adachi, Chihaya, Chemical Communications (Cambridge, 2015, 51(46), 9443-9446

合成路线：1 步