Luận án tiến sĩ nghiên cứu cấu trúc và tính chất một số hệ vòng ngưng tụ chứa lưu huỳnh và silic ứng dụng trong chế tạo vật liệu quang điện

BỘ GIÁO DỤC VÀ ĐÀO TẠO TRƯỜNG ĐẠI HỌC SƯ PHẠM HÀ NỘI - TRẦN NGỌC DŨNG Nghiên cứu cấu trúc tính chất số hệ vòng ngưng tụ chứa lưu huỳnh silic ứng dụng chế tạo vật liệu quang điện Chuyên ngành: Hóa lý thuyết Hóa lý Mã số: 9440119 Người hướng dẫn khoa học : PGS.TS Nguyễn Thị Minh Huệ PGS.TS Nguyễn Hiển Hà Nội - 2022 i LỜI CAM ĐOAN Tôi xin cam đoan luận án kết nghiên cứu cá nhân tơi Các số liệu tài liệu trích dẫn luận án thực cách trung thực Kết nghiên cứu không trùng với cơng trình cơng bố trước Tơi xin chịu trách nhiệm với lời cam đoan Hà Nội, tháng năm 2022 Nghiên cứu sinh Trần Ngọc Dũng ii LỜI CẢM ƠN ===**=== Trước tiên, em xin bày tỏ lòng biết ơn sâu sắc trân trọng tới cô PGS.TS Nguyễn Thị Minh Huệ thầy PGS.TS Nguyễn Hiển bảo, hướng dẫn, động viên giúp đỡ em tận tình suốt thời gian thực hoàn thành luận án Em xin chân thành cảm ơn hỗ trợ nhiệt tình NCS Nguyễn Văn Tráng, Viện Kỹ thuật nhiệt đới, Viện Hàn lâm Khoa học Công nghệ Việt Nam suốt thời gian em hoàn thành luận án Em xin tỏ lòng biết ơn sâu sắc chân thành đến tồn thể Thầy, Cơ Bộ mơn Hóa lý thuyết Hóa lý Bộ Mơn Hố học Hữu Thầy, Cô, anh chị làm việc Trung tâm Khoa học tính tốn, Trường Đại học Sư phạm Hà Nội tạo điều kiện cho em trình thực đề tài Cuối cùng, em xin gửi lời biết ơn sâu sắc tới người thân gia đình ln động viên hỗ trợ em để em tập trung trí lực hoàn thành luận án Xin trân trọng cảm ơn! Hà Nội, tháng năm 2022 Nghiên cứu sinh Trần Ngọc Dũng iii MỤC LỤC MỤC LỤC iii DANH MỤC CÁC KÍ HIỆU VIẾT TẮT v MỤC LỤC HÌNH ẢNH vii MỤC LỤC BẢNG x MỞ ĐẦU 1 Lý chọn đề tài .1 Mục đích, nhiệm vụ nghiên cứu 3 Đối tượng phạm vi nghiên cứu .3 Ý nghĩa khoa học thực tiễn luận án Những điểm luận án CHƯƠNG 1: TỔNG QUAN 1.1 Cơ sở lý thuyết về vật liệu quang điện hữu .5 1.1.1 Cấu tạo chế hoạt động đi-ốt phát quang hữu .5 1.1.2 Cấu tạo chế hoạt động pin mặt trời chất màu nhạy quang .11 1.2 Cơ sở lý thuyết hoá học lượng tử 16 1.3 Cơ sở lý thuyết phản ứng Heck 19 1.4 Hệ chất nghiên cứu 22 1.4.1 Hệ chất ngưng tụ chứa lưu huỳnh 22 1.4.2 Hệ chất ngưng tụ chứa silic 28 1.4.3 Tình hình nghiên cứu hợp chất ngưng tụ chứa lưu huỳnh .33 1.4.4 Tình hình nghiên cứu hợp chất ngưng tụ chứa silic 36 CHƯƠNG 2: PHƯƠNG PHÁP NGHIÊN CỨU 39 2.1 Phương pháp nghiên cứu lý thuyết 39 2.1.1 Phương pháp phiếm hàm mật độ 39 2.1.2 Phương pháp phiếm hàm mật độ phụ thuộc thời gian 43 2.1.3 Bộ hàm sở 45 2.1.4 Khả truyền dẫn điện tích 45 2.1.5 Phương pháp tính tốn hóa học lượng tử 46 2.2 Phương pháp nghiên cứu thực nghiệm 47 2.2.1 Hóa chất 48 iv 2.2.2 Dụng cụ thiết bị 48 2.2.3 Quy trình phản ứng alkenyl hóa BDT 48 2.2.4 Phân tích cấu trúc sản phẩm 49 CHƯƠNG 3: KẾT QUẢ NGHIÊN CỨU VÀ THẢO LUẬN 50 3.1 Hệ chất ngưng tụ chứa lưu huỳnh 50 3.1.1 Nghiên cứu cấu trúc tính chất hợp chất lưỡng cực dựa dibenzothiophene ứng dụng làm vật liệu chất mang OLED hệ thứ hai 50 3.1.2 Tổng hợp 2-Alkenylbenzo[1,2-b:4,5-b’]dithiophene hệ xúc tác Pd/Cu/Ag nghiên cứu cấu trúc phương pháp phổ thực nghiệm tính tốn lý thuyết .61 3.1.3 Thiết kế hệ chất bithiophene liên hợp chứa silole số dị vòng năm cạnh cho vật liệu quang điện 69 3.2 Hệ ngưng tụ chứa silic 94 3.2.1 Nghiên cứu cấu trúc tính chất quang điện số dẫn suất dithienosilole 94 3.2.2 Nghiên cứu lý thuyết ảnh hưởng cầu nối π hệ chất hữu dạng D-π-A ứng dụng cho pin mặt trời polymer 111 KẾT LUẬN CHUNG 120 ĐỊNH HƯỚNG NGHIÊN CỨU TIẾP THEO 121 DANH MỤC CƠNG TRÌNH ĐÃ CÔNG BỐ 122 TÀI LIỆU THAM KHẢO .123 v DANH MỤC CÁC KÍ HIỆU VIẾT TẮT Viết tắt HOMO Nguyên tiếng Anh Highest occupied molecular Tạm dịch Orbital phân tử bị chiếm cao orbital Lowest unoccupied molecular Orbital phân tử không bị chiếm thấp orbital OLED Organic light emitting diode Đi-ốt phát quang hữu DSSC Dye sensitized solar cell Pin mặt trời chất màu nhạy quang OPV Organic photovoltaics Quang điện hữu OFET Organic field effect transistor Transistor hiệu ứng trường hữu OTFT Organic thin-film transistor Transistor màng mỏng hữu OSC Organic semiconductors Chất bán dẫn hữu AIE Aggregation induced emission Phát xạ tập hợp ACQ Aggregation caused quench Dập tắt tập hợp HBMC Heteronuclear Multiple Bond Phổ tương quan liên kết LUMO Correlation HSQC Heteronuclear Single Phổ tương quan lượng tử đơn nhân Quantum Coherence DFT Density functional theory Thuyết phiếm hàm mật độ TD-DFT Time-dependent density Thuyết phiếm hàm mật độ phụ thuộc functional theory thời gian TTA Triplet-triplet annihilation Triệt tiêu triplet-triplet HLCT Hybridized local and charge Lai hoá cục chuyển điện tích transfer TADF Thermally activated delayed Huỳnh quang trễ hoạt hóa nhiệt fluorescence IQE Internal quantum efficiency Hiệu suất lượng tử nội EQE External quantum efficiency Hiệu suất lượng tử ngoại vi PLQE Photoluminescence quantum Hiệu suất phát quang lượng tử efficiency SOMO Singly occupied molecular Orbital phân tử singlet bị chiếm orbital Singly unoccupied molecular Orbital phân tử singlet không bị orbital chiếm LDA Local density approximation Xấp xỉ mật độ địa phương GGA Generalized gradient Gradient tổng quát SUMO approximation EA Electron affinity Ái lực electron IP Ionization potential Thế oxi hoá EHOMO HOMO energy Năng lượng HOMO ELUMO LUMO energy Năng lượng LUMO Egap Band-gap energy Năng lượng HOMO-LUMO S0 Singlet ground state Trạng thái singlet S1 First singlet excited state Trạng thái kích thích singlet thứ T1 First triplet excited state Trạng thái kích thích triplet thứ ES0 Singlet ground state energy Năng lượng trạng thái singlet ES1 First singlet excited state Năng lượng trạng thái kích thích energy singlet thứ First triplet excited state Năng lượng trạng thái kích thích energy triplet thứ λh Hole reorganization energy Năng lượng tái tổ hợp cho electron λe Electron reorganization Năng lượng tái tổ hợp cho lỗ trống ET1 energy λabs Absortion wavelength Bước sóng hấp thụ λem Emission wavelength Bước sóng phát xạ vii MỤC LỤC HÌNH ẢNH Hình 1.1: Cấu tạo điốt phát quang đại .6 Hình 1.2: Cơ chế phát huỳnh quang vật liệu hữu cơ: a) Huỳnh quang thông thường; b) Triệt tiêu triplet-triplet; c) Lai hoá cục vận chuyển điện tích; d) Huỳnh quang trễ hoạt hố nhiệt .8 Hình 1.3: Cấu hình spin a) phân tử vỏ đóng b) phân tử vỏ mở trạng thái kích thích 10 Hình 1.4: Sơ đồ cấu tạo pin mặt trời chất màu nhạy quang 12 Hình 1.5: Cấu trúc chất màu N3 (bên trái) N719 (bên phải) 15 Hình 1.6: Sơ đồ phản ứng Heck 20 Hình 1.7: Cơ chế phản ứng Heck đề xuất Carbi Candiani 21 Hình 1.8: Cấu tạo phân tử thiophene 22 Hình 1.9: Một số cấu trúc ngưng tụ chứa thiophene 23 Hình 1.10: Cấu tạo hợp chất gốc M0 25 Hình 1.11: Cấu trúc chất màu nhạy quang chứa BDT 26 Hình 1.12: Cấu trúc dẫn xuất BDT sử dụng thiết bị quang điện .26 Hình 1.13: Cấu trúc hệ chất bithiophene 28 Hình 1.14: Cấu tạo phân tử silole 29 Hình 1.15: Cấu trúc hệ chất dị vòng ngưng tụ dithienosilole 30 Hình 1.16: Cấu trúc phân tử PBDTS-TZNT 33 Hình 1.17: Cấu trúc hợp chất dithiophene dibenzothiophene 34 Hình 1.18: Cấu trúc polymer chứa thiophene .35 Hình 1.19: Cấu trúc hợp chất dithiophene ứng dụng DSSC 36 Hình 1.20: Một số hợp chất ngưng tụ chứa silic ứng dụng làm vật liệu phát xạ …………………………………………………………………………………… 38 Hình 1.21: Một số hợp chất ngưng tụ chứa silic ứng dụng làm vật liệu truyền dẫn điện tích ……………………………………………………………………….38 Hình 2.1: Sơ đồ phản ứng alkenyl hóa BDT ………………………………………49 viii Hình 3.1: Cấu trúc hợp chất nghiên cứu dựa nhóm Cz, DBTa DBTb cấu trúc hợp chất tham khảo gồm CBP, Firpic, NPB Bphen đóng vai trò chất mang, vật liệu phát xạ, vật liệu vận chuyển lỗ trống vận chuyển electron 50 Hình 3.2: Hình ảnh mức lượng HOMO LUMO hợp chất nghiên cứu hợp chất tham chiếu (eV) a) Đối với hợp chất Cz1-Cz7; b) Đối với hợp chất D1a-D7a; c) Đối với hợp chất D1b-D7b 53 Hình 3.3: Đồ thị IP EA hợp chất nghiên cứu so sánh với hợp chất tham chiếu (eV) .59 Hình 3.4: Sơ đồ tổng hợp hiệu suất 61 Hình 3.5: Cấu dạng hai đồng phân 3a-A 3a-B 61 Hình 3.6: Phổ HSQC (bên trái) phổ HMBC (bên phải) hợp chất 3a 64 Hình 3.7: Phổ NOESY 3a 65 Hình 3.8: Hình ảnh HOMO LUMO với mức lượng HOMO, LUMO Egap hợp chất (eV) .68 Hình 3.9: Cấu trúc hợp chất bithiophene nghiên cứu 70 Hình 3.10: Góc nhị nhiện hợp chất DTSPh dạng trung hoà, anion cation 74 Hình 3.11: Độ dài cầu nối hợp chất DTSPh dạng trung hoà, anion cation 74 Hình 3.12: Hình dạng mức lượng HOMO, LUMO hợp chất (eV) a) CPDT; b) DTP; c) DTSH; d) DTSMe; e) DTT; f) DTSPh .78 Hình 3.13: Phổ hấp thụ mơ hợp chất tính tốn TDB3LYP/6-31G(d, p) với mơ hình PCM dung môi THF: a) CPDT; b) DTP; c) DTSH; d) DTSMe; e) DTT; f) DTSPh 88 Hình 3.14: Phổ phát xạ hợp chất thu từ tính tốn TD-DFT/B3LYP/631G (d, p) với mơ hình PCM dung mơi THF a) CPDT; b) DTP; c) DTSH; d) DTSMe; e) DTT; f) DTSPh .93 Hình 3.15: Cấu trúc hợp chất hệ dithienosilole 95 Hình 3.16: Mức lượng HOMO LUMO hợp chất CBP, DTS hợp chất 1-11 100 ix Hình 3.17:a) Phổ hấp thụ hợp chất DTS, – 5; b) Phổ phát xạ hợp chất DTS, – 5; c) Phổ hấp thụ hợp chất – 11;d) Phổ phát xạ hợp chất - 11 106 Hình 3.18: Cấu trúc hợp chất 10a-10d .109 Hình 3.19: Hình ảnh HOMO LUMO hợp chất 10a-10d 110 Hình 3.20: Hệ chất nghiên cứu PBDTS-TZNT .112 Hình 3.21: Phân bố HOMO LUMO hợp chất thiết kế 116 Hình 3.22: Phổ hấp thụ hợp chất tính tốn môi trường dung môi clobenzen 119 121 - Đã nghiên cứu cách hệ thống dẫn xuất dithienosilole, kết cho thấy hợp chất có khả vận chuyển điện tích tốt, thích hợp sử dụng làm vật liệu truyền dẫn thiết bị OLED, đặc biệt hợp chất dạng dime - Kết tính tốn hợp chất DTS hệ chất nghiên cứu có giá trị Egap 2,5 eV, thấp so với 2,7 hợp chất gốc tổng hợp trước đó; Các giá trị λh, λe 0,23 0,21, tương đồng so với 0,23 0,21 hợp chất gốc, đồng thời phổ hấp thụ có bước chuyển dịch đỏ cường độ hấp thụ cao ĐỊNH HƯỚNG NGHIÊN CỨU TIẾP THEO Từ kết nghiên cứu, kiến nghị hướng nghiên cứu tập trung vào số nội dung sau: Mở rộng nghiên cứu tính chất cấu trúc dị vòng ngưng tụ khác nhằm ứng dụng chế tạo vật liệu quang điện hữu dị vòng khác dị vòng chứa borole, nitrogen Tiến hành tổng hợp ghép thêm hợp phần nhận electron cho hệ chất BDT (hệ chất 2) để tạo nên hợp chất dạng D-π-A hoàn chỉnh Tổng hợp hợp chất PBDTSTZNT với cầu nối dị vòng DTS hệ chất thứ Tổng hợp hợp chất D3a D3b hệ chất thứ để chế tạo thiết bị OLED Trên sở hợp chất tổng hợn, tiến hành chế tạo thiết bị DSSC OLED tương ứng, từ khảo sát tính chất về phổ, trình hoạt động thiết bị so sánh với kết tính tốn lý thuyết thực 122 DANH MỤC CƠNG TRÌNH ĐÃ CƠNG BỐ 1) Nguyen Van Trang, Tran Ngoc Dung, Tran Thi Thoa, Dinh Thi Mai Thanh, and Nguyen Thi Minh Hue "Stability and Semi‐Conductive Property of Some Derivatives of Mono‐and Di‐Silole: A Theoretical Study." Vietnam Journal of Chemistry 57, no (2019): 507-13 2) Tran Ngoc Dung, Nguyen Van Trang, Dinh Thi Mai Thanh, Nguyen Thi Van Khanh, Hien Nguyen, and Hue Minh Thi Nguyen "A Facile Regioselectively Synthesis of 2-Alkenylbenzo [1, 2-B: 4, 5-B’] Dithiophene by Pd/Cu/Ag-Catalyzed Ch Functionalization." ChemistrySelect 5, no 19 (2020): 5581-86 3) Tran Ngoc Dung, Nguyen Van Trang, Tran Thi Thoa, Phan Thi Thuy, Dinh Thi Mai Thanh, and Nguyen Thi Minh Hue "Theoretical Study of Structures and Properties of Some Silole Compounds." Vietnam Journal of Chemistry 58, no (2020): 212-20 4) Nguyen Van Trang, Tran Ngoc Dung, Ngo Tuan Cuong, Le Thi Hong Hai, Daniel Escudero, Minh Tho Nguyen, and Hue Minh Thi Nguyen "Theoretical Study of a Class of Organic D-Π-a Dyes for Polymer Solar Cells: Influence of Various ΠSpacers." Crystals 10, no (2020): 163 5) Nguyen Van Trang, Tran Ngoc Dung, Long Van Duong, My Phuong PhamHo, Hue Minh Thi Nguyen, and Minh Tho Nguyen "Structural, Electronic, and Optical Properties of Some New Dithienosilole Derivatives." Structural Chemistry 31, no (2020): 2215-25 6) Nguyen Van Trang, Nguyen Minh Tam, Tran Ngoc Dung, and Minh Tho Nguyen "A Theoretical Design of Bipolar Host Materials for Blue Phosphorescent Oled." Journal of Molecular Graphics and Modelling 105 (2021): 107845 7) Hue Minh Thi Nguyen, Tran Ngoc Dung, Nguyen Van Trang, Ngo Tuan Cuong, Nguyen Van Minh, Hien Nguyen, and Minh Tho Nguyen "Design of Fused Bithiophene Systems Containing Silole and Five-Membered Heterocycles for Optoelectronic Materials." 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