TW202026303A - Organometallic compound and organic light-emitting device including the same - Google Patents

Abstract

An organometallic compound represented by Formula 1 and an organic light-emitting device including the same, and Y2, ring A2, R1 to R8, R13 to R20, and d2 in Formula 1 may be each independently the same as described in the specification.

Description

Organometallic compound and organic light emitting device including the same

The present disclosure relates to organometallic compounds and organic light-emitting devices including them. [Cross references to related applications]

This application requires the rights of Korean Patent Application No. 10-2018-0173083 filed on December 28, 2018 and Korean Patent Application No. 10-2019-0136792 filed on October 30, 2019 at the Korean Intellectual Property Office and All rights and interests arising from it. All its contents are incorporated into this article as a reference.

Organic light-emitting devices are self-emissive devices that have improved characteristics in terms of viewing angle, response time, brightness, driving voltage, and response speed, and generate full-color images.

In an example, the organic light emitting device includes an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer includes an emission layer. The hole transport area may be between the anode and the emission layer, and the electron transport area may be between the emission layer and the cathode. The holes provided from the anode may move toward the emission layer through the hole transport area, and the electrons provided from the cathode may move toward the emission layer through the electron transport area. Holes and electrons recombine in the emission layer to generate excitons. These excitons transition from the excited state to the ground state, thereby generating light.

Provide new organometallic compounds and organic light-emitting devices including them.

Other aspects will be partly clarified in the following description, and partly will be clarified by the description, or may be learned through the practice of the provided embodiments.

在式1中， Y₂ 可為C， 環A₂ 可為C₅ -C₃₀ 碳環基團或C₁ -C₃₀ 雜環基團， R₁ -R₈ 、R₁₃ -R₁₇ 和R₂₀ 可各自獨立地為氫、氘、-F、-Cl、-Br、-I、-SF₅ 、羥基、氰基、硝基、氨基、脒基、肼基、腙基、羧酸基團或其鹽、磺酸基團或其鹽、磷酸基團或其鹽、經取代或未經取代的C₁ -C₆₀ 烷基、經取代或未經取代的C₂ -C₆₀ 烯基、經取代或未經取代的C₂ -C₆₀ 炔基、經取代或未經取代的C₁ -C₆₀ 烷氧基、經取代或未經取代的C₃ -C₁₀ 環烷基、經取代或未經取代的C₂ -C₁₀ 雜環烷基、經取代或未經取代的C₃ -C₁₀ 環烯基、經取代或未經取代的C₂ -C₁₀ 雜環烯基、經取代或未經取代的C₆ -C₆₀ 芳基、經取代或未經取代的C₆ -C₆₀ 芳氧基、經取代或未經取代的C₆ -C₆₀ 芳硫基、經取代或未經取代的C₁ -C₆₀ 雜芳基、經取代或未經取代的單價非芳族稠合多環基團、經取代或未經取代的單價非芳族稠合雜多環基團、-N(Q₁ )(Q₂ )、-Si(Q₃ )(Q₄ )(Q₅ )、-Ge(Q₃ )(Q₄ )(Q₅ )、-B(Q₆ )(Q₇ )、-P(=O)(Q₈ )(Q₉ )、或-P(Q₈ )(Q₉ )， 條件是i) R₁ -R₈ 的至少一個可包括至少一個氟基團(-F)，且ii) R₂₀ 可既不包括氟基團(-F)也不包括氰基， d2可為0-10的整數，且當d2為2或更大時，兩個或更多個R₂₀ 可彼此相同或不同， R₁₈ 和R₁₉ 可各自獨立地為經取代或未經取代的C₂ -C₆₀ 烷基、經取代或未經取代的C₂ -C₆₀ 烯基、經取代或未經取代的C₂ -C₆₀ 炔基、經取代或未經取代的C₁ -C₆₀ 烷氧基、經取代或未經取代的C₃ -C₁₀ 環烷基、經取代或未經取代的C₂ -C₁₀ 雜環烷基、經取代或未經取代的C₃ -C₁₀ 環烯基、經取代或未經取代的C₂ -C₁₀ 雜環烯基、經取代或未經取代的C₆ -C₆₀ 芳基、經取代或未經取代的C₆ -C₆₀ 芳氧基、經取代或未經取代的C₆ -C₆₀ 芳硫基、經取代或未經取代的C₁ -C₆₀ 雜芳基、經取代或未經取代的單價非芳族稠合多環基團、或者經取代或未經取代的單價非芳族稠合雜多環基團， R₁ -R₈ 的兩個或更多個可任選地連接以形成未經取代的或被至少一個R_1a 取代的C₅ -C₃₀ 碳環基團、或者未經取代的或被至少一個R_1a 取代的C₁ -C₃₀ 雜環基團， 數量為d2的R₂₀ 的兩個或更多個可任選地連接以形成未經取代的或被至少一個R_1a 取代的C₅ -C₃₀ 碳環基團、或者未經取代的或被至少一個R_1a 取代的C₁ -C₃₀ 雜環基團， R₁₃ -R₁₉ 的兩個或更多個可任選地連接以形成未經取代的或被至少一個R_1a 取代的C₅ -C₃₀ 碳環基團、或者未經取代的或被至少一個R_1a 取代的C₁ -C₃₀ 雜環基團， R_1a 可與關於R₂ 所說明的相同， 經取代的C₁ -C₆₀ 烷基、經取代的C₂ -C₆₀ 烷基、經取代的C₂ -C₆₀ 烯基、經取代的C₂ -C₆₀ 炔基、經取代的C₁ -C₆₀ 烷氧基、經取代的C₃ -C₁₀ 環烷基、經取代的C₂ -C₁₀ 雜環烷基、經取代的C₃ -C₁₀ 環烯基、經取代的C₂ -C₁₀ 雜環烯基、經取代的C₆ -C₆₀ 芳基、經取代的C₆ -C₆₀ 芳氧基、經取代的C₆ -C₆₀ 芳硫基、經取代的C₁ -C₆₀ 雜芳基、經取代的單價非芳族稠合多環基團和取代的單價非芳族稠合雜多環基團的取代基為： 氘、-F、-Cl、-Br、-I、-CD₃ 、-CD₂ H、-CDH₂ 、-CF₃ 、-CF₂ H、-CFH₂ 、羥基、氰基、硝基、氨基、脒基、肼基、腙基、羧酸基團或其鹽、磺酸基團或其鹽、磷酸基團或其鹽、C₁ -C₆₀ 烷基、C₂ -C₆₀ 烯基、C₂ -C₆₀ 炔基或C₁ -C₆₀ 烷氧基或其任意組合； C₁ -C₆₀ 烷基、C₂ -C₆₀ 烯基、C₂ -C₆₀ 炔基或C₁ -C₆₀ 烷氧基各自經以下取代：氘、-F、-Cl、-Br、-I、-CD₃ 、-CD₂ H、-CDH₂ 、-CF₃ 、-CF₂ H、-CFH₂ 、羥基、氰基、硝基、氨基、脒基、肼基、腙基、羧酸基團或其鹽、磺酸基團或其鹽、磷酸基團或其鹽、C₃ -C₁₀ 環烷基、C₂ -C₁₀ 雜環烷基、C₃ -C₁₀ 環烯基、C₂ -C₁₀ 雜環烯基、C₆ -C₆₀ 芳基、C₆ -C₆₀ 芳氧基、C₆ -C₆₀ 芳硫基、C₁ -C₆₀ 雜芳基、單價非芳族稠合多環基團、單價非芳族稠合雜多環基團、-N(Q₁₁ )(Q₁₂ )、-Si(Q₁₃ )(Q₁₄ )(Q₁₅ )、-Ge(Q₁₃ )(Q₁₄ )(Q₁₅ )、-B(Q₁₆ )(Q₁₇ )、-P(=O)(Q₁₈ )(Q₁₉ )、-P(Q₁₈ )(Q₁₉ )、或其任意組合； C₃ -C₁₀ 環烷基、C₂ -C₁₀ 雜環烷基、C₃ -C₁₀ 環烯基、C₂ -C₁₀ 雜環烯基、C₆ -C₆₀ 芳基、C₆ -C₆₀ 芳氧基、C₆ -C₆₀ 芳硫基、C₁ -C₆₀ 雜芳基、單價非芳族稠合多環基團或單價非芳族稠合雜多環基團各自未經取代或經以下取代：氘、-F、-Cl、-Br、-I、-CD₃ 、-CD₂ H、-CDH₂ 、-CF₃ 、-CF₂ H、-CFH₂ 、羥基、氰基、硝基、氨基、脒基、肼基、腙基、羧酸基團或其鹽、磺酸基團或其鹽、磷酸基團或其鹽、C₁ -C₆₀ 烷基、C₂ -C₆₀ 烯基、C₂ -C₆₀ 炔基、C₁ -C₆₀ 烷氧基、C₃ -C₁₀ 環烷基、C₂ -C₁₀ 雜環烷基、C₃ -C₁₀ 環烯基、C₂ -C₁₀ 雜環烯基、C₆ -C₆₀ 芳基、C₆ -C₆₀ 芳氧基、C₆ -C₆₀ 芳硫基、C₁ -C₆₀ 雜芳基、單價非芳族稠合多環基團、單價非芳族稠合雜多環基團、-N(Q₂₁ )(Q₂₂ )、-Si(Q₂₃ )(Q₂₄ )(Q₂₅ )、-Ge(Q₂₃ )(Q₂₄ )(Q₂₅ )、-B(Q₂₆ )(Q₂₇ )、-P(=O)(Q₂₈ )(Q₂₉ )、-P(Q₂₈ )(Q₂₉ )或其任意組合； -N(Q₃₁ )(Q₃₂ )、-Si(Q₃₃ )(Q₃₄ )(Q₃₅ )、-Ge(Q₃₃ )(Q₃₄ )(Q₃₅ )、-B(Q₃₆ )(Q₃₇ )、-P(=O)(Q₃₈ )(Q₃₉ )或-P(Q₃₈ )(Q₃₉ )、或其任意組合；或 其任意組合， 其中Q₁ -Q₉ 、Q₁₁ -Q₁₉ 、Q₂₁ -Q₂₉ 和Q₃₁ -Q₃₉ 可各自獨立地為：氫；氘；-F；-Cl；-Br；-I；羥基；氰基；硝基；脒基；肼基；腙基；羧酸基團或其鹽；磺酸基團或其鹽；磷酸基團或其鹽；未經取代的或者被氘、C₁ -C₆₀ 烷基、C₆ -C₆₀ 芳基或其任意組合取代的C₁ -C₆₀ 烷基；C₂ -C₆₀ 烯基；C₂ -C₆₀ 炔基；C₁ -C₆₀ 烷氧基；C₃ -C₁₀ 環烷基；C₂ -C₁₀ 雜環烷基；C₃ -C₁₀ 環烯基；C₂ -C₁₀ 雜環烯基；未經取代的或者被氘、C₁ -C₆₀ 烷基、C₆ -C₆₀ 芳基、或其任意組合取代的C₆ -C₆₀ 芳基；C₆ -C₆₀ 芳氧基；C₆ -C₆₀ 芳硫基；C₁ -C₆₀ 雜芳基；單價非芳族稠合多環基團；或單價非芳族稠合雜多環基團。According to an aspect of the embodiment, there is provided an organometallic compound represented by Formula 1: [Formula 1]

In formula 1, Y ₂ can be C, ring A ₂ can be a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group, R ₁ -R ₈ , R ₁₃ -R ₁₇ and R ₂₀ Can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or Salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C ₁ -C ₆₀ alkyl, substituted or unsubstituted C ₂ -C ₆₀ alkenyl, substituted or Unsubstituted C ₂ -C ₆₀ alkynyl, substituted or unsubstituted C ₁ -C ₆₀ alkoxy, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenyl, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q ₁ ) (Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -Ge(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ), -P(= O)(Q ₈ )(Q ₉ ), or -P(Q ₈ )(Q ₉ ), provided that i) at least one of R ₁ -R ₈ may include at least one fluorine group (-F), and ii) R ₂₀ may include neither a fluoro group (-F) nor a cyano group, d2 may be an integer of 0-10, and when d2 is 2 or greater, two or more R ₂₀ may be the same as each other or Different, R ₁₈ and R ₁₉ may each independently be substituted or unsubstituted C ₂ -C ₆₀ alkyl, substituted or unsubstituted C ₂ -C ₆₀ alkenyl, substituted or unsubstituted C ₂ -C ₆₀ alkynyl, substituted or unsubstituted C ₁ -C ₆₀ alkoxy, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenyl, substituted or unsubstituted C ₆ -C ₆₀ aryl, substituted or unsubstituted C ₆ -C ₆₀ aryloxy, substituted or unsubstituted C ₆ -C ₆₀ arylthio, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl Group, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, R _{1 8} -R two or more can be linked to form an optionally unsubstituted or substituted with at least one R _1a is C ₅ -C ₃₀ carbocyclic radical, unsubstituted or substituted with at least one R _1a A substituted C ₁ -C ₃₀ heterocyclic group, two or more of R ₂₀ in number d2 may be optionally joined to form a C ₅ -C ₃₀ carbon that is unsubstituted or substituted with at least one R _1a A cyclic group, or a C ₁ -C ₃₀ heterocyclic group that is unsubstituted or substituted with at least one R _1a , two or more of R ₁₃ -R ₁₉ may be optionally connected to form an unsubstituted at least one R _1a substituent or the C ₅ -C ₃₀ carbocyclic group, or an unsubstituted or substituted by at least one R _1a is C ₁ -C ₃₀ heterocyclic group, R _1a may be described with respect to R ₂ The same, substituted C ₁ -C ₆₀ alkyl, substituted C ₂ -C ₆₀ alkyl, substituted C ₂ -C ₆₀ alkenyl, substituted C ₂ -C ₆₀ alkynyl, substituted C ₁ -C ₆₀ alkoxy, substituted C ₃ -C ₁₀ cycloalkyl, substituted C ₂ -C ₁₀ heterocycloalkyl, substituted C ₃ -C ₁₀ cycloalkenyl, substituted C _2- C ₁₀ heterocycloalkenyl, substituted C ₆ -C ₆₀ aryl, substituted C ₆ -C ₆₀ aryloxy, substituted C ₆ -C ₆₀ arylthio, substituted C _1- The substituents of C ₆₀ heteroaryl, substituted monovalent non-aromatic fused polycyclic group and substituted monovalent non-aromatic fused heteropolycyclic group are: deuterium, -F, -Cl, -Br,- I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid Group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl or C ₁ -C ₆₀ alkane Oxy or any combination thereof; C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, or C ₁ -C ₆₀ alkoxy are each substituted by deuterium, -F,- Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl, cyano, nitro, amino, amidino, hydrazino, Hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ Cycloalkenyl, C ₂ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl, monovalent Non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropoly Ring group, -N(Q ₁₁ )(Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -Ge(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -B(Q ₁₆ )(Q ₁₇ ), -P(=O)(Q ₁₈ )(Q ₁₉ ), -P(Q ₁₈ )(Q ₁₉ ), or any combination thereof; C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₂ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio , C ₁ -C ₆₀ heteroaryl, monovalent non-aromatic fused polycyclic group or monovalent non-aromatic fused heteropolycyclic group are each unsubstituted or substituted by the following: deuterium, -F, -Cl,- Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, Carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C _1- C ₆₀ alkoxy, C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₂ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl Group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group Group, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ), -Ge(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ), -B(Q ₂₆ )( Q ₂₇ ), -P(=O)(Q ₂₈ )(Q ₂₉ ), -P(Q ₂₈ )(Q ₂₉ ) or any combination thereof; -N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -Ge(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -B(Q ₃₆ )(Q ₃₇ ), -P(=O)(Q ₃₈ )(Q ₃₉ ) Or -P(Q ₃₈ )(Q ₃₉ ), or any combination thereof; or any combination thereof, wherein Q ₁ -Q ₉ , Q ₁₁ -Q ₁₉ , Q ₂₁ -Q ₂₉ and Q ₃₁ -Q ₃₉ may be independently Is: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; amidino; hydrazine; hydrazone; carboxylic acid group or its salt; sulfonic acid group or its salt ; a phosphoric acid group or a salt thereof; unsubstituted or substituted by deuterium, C ₁ -C ₆₀ alkyl, C ₆ -C ₆₀ aryl group, or any combination of the substituted C ₁ -C ₆₀ alkyl; C ₂ - C ₆₀ alkenyl; C ₂ -C ₆₀ alkynyl; C ₁ -C ₆₀ alkoxy; C ₃ -C ₁₀ cycloalkyl; C ₂ -C ₁₀ heterocycloalkyl; C ₃ -C ₁₀ cycloalkenyl; alkenyl C ₂ -C ₁₀ heterocyclyl group; unsubstituted or substituted by deuterium, C ₁ -C ₆₀ alkyl, C ₆ -C ₆₀ aryl group, or any combination thereof C ₆ -C ₆₀ substituted aryl group; C ₆ -C ₆₀ aryloxy; C ₆ -C ₆₀ arylthio; C ₁ -C ₆₀ heteroaryl; monovalent non-aromatic fused polycyclic group; or monovalent non-aromatic fused heteropolycyclic group.

Another aspect provides an organic light emitting device including: a first electrode; a second electrode; and an organic layer provided between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes at least An organometallic compound represented by Formula 1.

The organometallic compound may be included in the emission layer of the organic layer and may function as a dopant.

The embodiments will now be described in detail, examples of which are illustrated in the drawings, in which the same reference numerals always refer to the same elements. In this regard, the present embodiment may have different forms and should not be construed as being limited to the description set forth herein. Therefore, the embodiments are described below only by referring to the drawings to illustrate aspects of this description. As used herein, the term "and/or" includes any and all combinations of one or more of the related listed items. Expressions such as "at least one (species) of" when preceding or following a list of elements modify the entire list of elements and do not modify individual elements of the list.

It will be understood that when an element is referred to as being "on" another element, it can be directly on the other element or intervening elements may be present therebetween. In contrast, when an element is referred to as being "directly on" another element, there are no intervening elements.

It will be understood that although the terms "first", "second", "third", etc. may be used herein to describe various elements, components, regions, layers and/or parts, these elements, components, regions, Layers and/or parts should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer or section from another element, component, region, layer or section. Therefore, without departing from the teachings herein, a first element, component, region, layer or section discussed below may be referred to as a second element, component, region, layer or section.

The terminology used herein is only for the purpose of describing specific embodiments and is not intended to be limiting. As used herein, "a", "an", "said (the)" and "at least one (kind)" do not denote quantitative limitations, and are intended to cover both singular and plural numbers, unless the context dictates otherwise. For example, "element" has the same meaning as "at least one element" unless the context dictates otherwise.

"Or" means "and/or". As used herein, the term "and/or" includes any and all combinations of one or more of the related listed items. It will be further understood that the term "comprising" or "including" when used in this specification indicates the presence of the stated features, regions, wholes, steps, operations, elements and/or components, but does not exclude the presence or addition of one or Various additional features, regions, wholes, steps, operations, elements, components, and/or collections thereof.

In addition, relative terms such as "lower" or "bottom" and "upper" or "top" may be used herein to describe the relationship between one element and another element as shown in the figure. It will be understood that in addition to the orientation depicted in the figures, relative terms are also intended to include different orientations of the device. For example, if the device in one of the figures is turned over, the elements described as being "on" the "lower" side of another element will then be oriented on the "upper" side of the other element. Therefore, depending on the specific orientation of the figure, the exemplary term "lower" may include both "lower" and "upper" orientations. Similarly, if the device in one of the figures is turned over, elements described as "below" or "beneath" another element will be oriented "above" the other element. Therefore, the exemplary terms "below" or "below" can include both orientations above and below.

As used herein, "about" or "approximately" includes the stated value and means that the measurement and the error associated with the measurement of the specific quantity (ie, the limitation of the measurement system) as discussed by those of ordinary skill in the art And determine the acceptable deviation range for the specific value. For example, "about" can mean that the deviation from the stated value is within one or more standard deviations, or within ±10% or 5%.

Unless otherwise defined, the meanings of all terms (including technical and scientific terms) used herein are the same as those commonly understood by those of ordinary skill in the art to which this disclosure belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as their meaning consistent with their background in the relevant field and the meaning in this disclosure, and will not be interpreted in an idealized or overly formal meaning , Unless clearly defined as such in this article.

Exemplary embodiments are described herein with reference to cross-sectional views as schematic diagrams of idealized embodiments. In this way, deviations from the shape of the figure are expected as a result of, for example, manufacturing technology and/or tolerances. Therefore, the embodiments described herein should not be construed as being limited to the specific shape of the region as shown herein, but include deviations in shape caused by, for example, manufacturing. For example, regions illustrated or described as flat may typically have rough and/or non-linear characteristics. In addition, the illustrated sharp corners may be rounded. Therefore, the regions shown in the figures are schematic in nature, and their shapes are not intended to illustrate the precise shape of the regions, and are not intended to limit the scope of the patent scope of this application.

式1中的Y₂ 可為C。 式1中的環A₂ 可為C₅ -C₃₀ 碳環基團或C₁ -C₃₀ 雜環基團。 例如，式1中的環A₂ 可為i)第一環，ii)第二環，iii)其中兩個或更多個第一環彼此稠合的稠環基團，iv)其中兩個或更多個第二環彼此稠合的稠環基團，或v)其中至少一個第一環與至少一個第二環稠合的稠環基團， 所述第一環可為環戊烷基團、環戊二烯基團、呋喃基團、噻吩基團、吡咯基團、噻咯基團、茚基團、苯並呋喃基團、苯並噻吩基團、吲哚基團、苯並噻咯基團、噁唑基團噁、異噁唑基團、噁二唑基團、異噁二唑基團、噁三唑基團、異噁三唑基團、噻唑基團、異噻唑基團、噻二唑基團、異噻二唑基團、噻三唑基團、異噻三唑基團、吡唑基團、咪唑基團、三唑基團、四唑基團、氮雜噻咯基團、二氮雜噻咯基團、或三氮雜噻咯基團， 所述第二環可為金剛烷基團、降冰片烯基團、二環[1.1.1]戊烷基團、二環[2.1.1]己烷基團、二環[2.2.1]庚烷基團(降莰烷基團)、二環[2.2.2]辛烷基團、環己烷基團、環己烯基團、苯基團、吡啶基團、嘧啶基團、吡嗪基團、噠嗪基團、或三嗪基團。The organometallic compound according to the embodiment is represented by the following Formula 1: [Formula 1]

Y _{2 in} Formula 1 may be C. Ring A ₂ in Formula 1 may be a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group. For example, ring A ₂ in Formula 1 may be i) the first ring, ii) the second ring, iii) a fused ring group in which two or more first rings are fused to each other, iv) two or More fused ring groups in which second rings are fused to each other, or v) fused ring groups in which at least one first ring is fused to at least one second ring, and the first ring may be a cyclopentyl group , Cyclopentadiene group, furan group, thiophene group, pyrrole group, silole group, indene group, benzofuran group, benzothiophene group, indole group, benzosilole Groups, oxazole groups, oxazole, isoxazole groups, oxadiazole groups, isoxadiazole groups, oxtriazole groups, isoxtriazole groups, thiazole groups, isothiazole groups, Thiadiazole group, isothiadiazole group, thiatriazole group, isothiatriazole group, pyrazole group, imidazole group, triazole group, tetrazole group, azathirolyl group Group, diazasilole group, or triazasilole group, the second ring may be an adamantyl group, a norbornene group, a bicyclo[1.1.1] pentane group, a Cyclo[2.1.1]hexane group, bicyclo[2.2.1]heptan group (norbornane group), bicyclo[2.2.2]octyl group, cyclohexane group, cyclohexane Alkenyl group, phenyl group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, or triazine group.

基團、1,2,3,4-四氫萘基團、噻吩基團、呋喃基團、吡咯基團、環戊二烯基團、噻咯基團、硼雜環戊二烯(borole)基團、磷雜環戊二烯(phosphole)基團、硒吩基團、鍺雜環戊二烯(germole)基團、苯並噻吩基團、苯並呋喃基團、吲哚基團、茚基團、苯並噻咯基團、苯並硼雜環戊二烯基團、苯並磷雜環戊二烯基團、苯並硒吩基團、苯並鍺雜環戊二烯基團、二苯並噻吩基團、二苯並呋喃基團、哢唑基團、芴基團、二苯並噻咯基團、二苯並硼雜環戊二烯基團、二苯並磷雜環戊二烯基團、二苯並硒吩基團、二苯並鍺雜環戊二烯基團、二苯並噻吩5-氧化物基團、9H-芴-9-酮基團、二苯並噻吩5,5-二氧化物基團、氮雜苯並噻吩基團、氮雜苯並呋喃基團、氮雜吲哚基團、氮雜茚基團、氮雜苯並噻咯基團、氮雜苯並硼雜環戊二烯基團、氮雜苯並磷雜環戊二烯基團、氮雜苯並硒吩基團、氮雜苯並鍺雜環戊二烯基團、氮雜二苯並噻吩基團、氮雜二苯並呋喃基團、氮雜哢唑基團、氮雜芴基團、氮雜二苯並噻咯基團、氮雜二苯並硼雜環戊二烯基團、氮雜二苯並磷雜環戊二烯基團、氮雜二苯並硒吩基團、氮雜二苯並鍺雜環戊二烯基團、氮雜二苯並噻吩5-氧化物基團、氮雜-9H-芴-9-酮基團、氮雜二苯並噻吩5,5-二氧化物基團、吡啶基團、嘧啶基團、吡嗪基團、噠嗪基團、三嗪基團、喹啉基團、異喹啉基團、喹喔啉基團、喹唑啉基團、菲咯啉基團、吡唑基團、咪唑基團、三唑基團、噁唑基團、異噁唑基團、噻唑基團、異噻唑基團、噁二唑基團、噻二唑基團、苯並吡唑基團、苯並咪唑基團、苯並噁唑基團、苯並噻唑基團、苯並噁二唑基團、苯並噻二唑基團、5,6,7,8-四氫異喹啉基團、5,6,7,8-四氫喹啉基團、金剛烷基團、降莰烷基團、或降冰片烯基團。In one or more embodiments, the ring A ₂ in Formula 1 may be a cyclopentane group, a cyclohexane group, a cyclohexene group, a phenyl group, a naphthalene group, an anthracene group, a phenanthrene group , Benzo[9,10]phenanthrene group, pyrene group,

Group, 1,2,3,4-tetrahydronaphthalene group, thiophene group, furan group, pyrrole group, cyclopentadiene group, silole group, borole Group, phosphole group, selenophene group, germanium heterolepene (germole) group, benzothiophene group, benzofuran group, indole group, indene Group, benzosilole group, benzoborole group, benzophosphoryl group, benzoselenophene group, benzogermantocyclopentadien group, Dibenzothiophene group, dibenzofuran group, azole group, fluorene group, dibenzosilole group, dibenzoborole group, dibenzophosphoryl group Diene group, dibenzoselenophene group, dibenzogermantocyclopentadiene group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, dibenzothiophene 5,5-dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, azaindene group, azabenzosilole group, aza Benzoborole group, azabenzophosphorene group, azabenzoselenophene group, azabenzogermantocyclopentadiene group, azadiphenyl Azathiophene group, azadibenzofuran group, azapyrazole group, azafluorene group, azadibenzosilole group, azadibenzoborole group , Azadibenzophosphoryl group, azadibenzoselenophene group, azadibenzogermantocyclopentadiene group, azadibenzothiophene 5-oxide group Group, aza-9H-fluorene-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, three Azinyl group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrazole group, imidazole group, triazole group, oxazoline group Group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzene Thiazole group, benzoxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroquinolinyl group Group, adamantyl group, norbornene group, or norbornene group.

In one or more embodiments, ring A ₂ can be a phenyl group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, a pyrrole group, a cyclopentadiene group Alkenyl group, silole group, benzothiophene group, benzofuran group, indole group, indene group, benzosilole group, dibenzothiophene group, dibenzofuran group , Azole group, fluorene group, or dibenzosilole group.

R ₁ -R ₈ , R ₁₃ -R ₁₇ and R _{20 in} formula 1 may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , hydroxyl, cyano, nitro , Amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C ₁ -C ₆₀ alkyl, Substituted or unsubstituted C ₂ -C ₆₀ alkenyl, substituted or unsubstituted C ₂ -C ₆₀ alkynyl, substituted or unsubstituted C ₁ -C ₆₀ alkoxy, substituted or unsubstituted Substituted C ₃ -C ₁₀ cycloalkyl, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl, substituted or unsubstituted Substituted C ₂ -C ₁₀ heterocycloalkenyl, substituted or unsubstituted C ₆ -C ₆₀ aryl, substituted or unsubstituted C ₆ -C ₆₀ aryloxy, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted Monovalent non-aromatic fused heteropolycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -Ge(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ), -P(=O)(Q ₈ )(Q ₉ ), or -P(Q ₈ )(Q ₉ ). Q ₁ -Q ₉ are each the same as described in this article. Here, R ₂₀ may include neither the fluorine group (-F) nor the cyano group. In one or more embodiments, R ₂₀ may be a group that includes neither a fluorine group (-F) nor a cyano group.

基、吡咯基、噻吩基、呋喃基、咪唑基、吡唑基、噻唑基、異噻唑基、噁唑基、異噁唑基、吡啶基、吡嗪基、嘧啶基、噠嗪基、異吲哚基、吲哚基、吲唑基、嘌呤基、喹啉基、異喹啉基、苯並喹啉基、喹喔啉基、喹唑啉基、噌啉基、哢唑基、菲咯啉基、苯並咪唑基、苯並呋喃基、苯並噻吩基、異苯並噻唑基、苯並噁唑基、異苯並噁唑基、三唑基、四唑基、噁二唑基、三嗪基、二苯並呋喃基、二苯並噻吩基、苯並哢唑基、二苯並哢唑基、咪唑並吡啶基、咪唑並嘧啶基、氮雜哢唑基、氮雜二苯並呋喃基、或氮雜二苯並噻吩基：氘、-F、-Cl、-Br、-I、-CD₃ 、-CD₂ H、-CDH₂ 、-CF₃ 、-CF₂ H、-CFH₂ 、羥基、氰基、硝基、氨基、脒基、肼基、腙基、羧酸基團或其鹽、磺酸基團或其鹽、磷酸基團或其鹽、C₁ -C₂₀ 烷基、含氘的C₁ -C₂₀ 烷基、氟化C₁ -C₂₀ 烷基、C₁ -C₂₀ 烷氧基、環戊基、環己基、環庚基、環辛基、金剛烷基、降冰片烯基、環戊烯基、環己烯基、環庚烯基、二環[1.1.1]戊基、二環[2.1.1]己基、二環[2.2.1]庚基、二環[2.2.2]辛基、(C₁ -C₂₀ 烷基)環戊基、(C₁ -C₂₀ 烷基)環己基、(C₁ -C₂₀ 烷基)環庚基、(C₁ -C₂₀ 烷基)環辛基、(C₁ -C₂₀ 烷基)金剛烷基、(C₁ -C₂₀ 烷基)降冰片烯基、(C₁ -C₂₀ 烷基)環戊烯基、(C₁ -C₂₀ 烷基)環己烯基、(C₁ -C₂₀ 烷基)環庚烯基、(C₁ -C₂₀ 烷基)二環[1.1.1]戊基、(C₁ -C₂₀ 烷基)二環[2.1.1]己基、(C₁ -C₂₀ 烷基)二環[2.2.1]庚基、(C₁ -C₂₀ 烷基)二環[2.2.2]辛基、矽雜環戊烷基、苯基、(C₁ -C₂₀ 烷基)苯基、聯苯基、三聯苯基、萘基、1,2,3,4-四氫萘基、芴基、菲基、蒽基、熒蒽基、苯並[9,10]菲基、芘基、

基、吡咯基、噻吩基、呋喃基、咪唑基、吡唑基、噻唑基、異噻唑基、噁唑基、異噁唑基、吡啶基、吡嗪基、嘧啶基、噠嗪基、異吲哚基、吲哚基、吲唑基、嘌呤基、喹啉基、異喹啉基、苯並喹啉基、喹喔啉基、喹唑啉基、噌啉基、哢唑基、菲咯啉基、苯並咪唑基、苯並呋喃基、苯並噻吩基、異苯並噻唑基、苯並噁唑基、異苯並噁唑基、三唑基、四唑基、噁二唑基、三嗪基、二苯並呋喃基、二苯並噻吩基、苯並哢唑基、二苯並哢唑基、咪唑並吡啶基、咪唑並嘧啶基、氮雜哢唑基、氮雜二苯並呋喃基、氮雜二苯並噻吩基、或其任意組合；或 -N(Q₁ )(Q₂ )、-Si(Q₃ )(Q₄ )(Q₅ )、-Ge(Q₃ )(Q₄ )(Q₅ )、-B(Q₆ )(Q₇ )、-P(=O)(Q₈ )(Q₉ )、或-P(Q₈ )(Q₉ )，其中R₂₀ 既不包括氟基團也不包括氰基， Q₁ -Q₉ 可各自獨立地為： -CH₃ 、-CD₃ 、-CD₂ H、-CDH₂ 、-CH₂ CH₃ 、-CH₂ CD₃ 、-CH₂ CD₂ H、-CH₂ CDH₂ 、-CHDCH₃ 、-CHDCD₂ H、-CHDCDH₂ 、-CHDCD₃ 、-CD₂ CD₃ 、-CD₂ CD₂ H或-CD₂ CDH₂ ；或 各自未被取代或被如下取代的正丙基、異丙基、正丁基、仲丁基、異丁基、叔丁基、正戊基、叔戊基、新戊基、異戊基、仲戊基、3-戊基、仲異戊基、苯基、聯苯基、或萘基：氘、C₁ -C₂₀ 烷基、苯基、或其任意組合。For example, R ₁ -R ₈ , R ₁₃ -R ₁₇ and R _{20 in} Formula 1 can each independently be: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, Amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, -SF ₅ , C ₁ -C ₂₀ alkyl, or C _1- C ₂₀ alkoxy; C ₁ -C ₂₀ alkyl or C ₁ -C ₂₀ alkoxy each substituted by deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H , -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or Its salt, phosphoric acid group or its salt, C ₁ -C ₂₀ alkyl, deuterium-containing C ₁ -C ₂₀ alkyl, fluorinated C ₁ -C ₂₀ alkyl, cyclopentyl, cyclohexyl, cycloheptyl, Cyclooctyl, adamantyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[ 2.2.1] Heptyl (norbornanyl), bicyclo[2.2.2] octyl, (C ₁ -C ₂₀ alkyl) cyclopentyl, (C ₁ -C ₂₀ alkyl) cyclohexyl, (C _1- C ₂₀ alkyl) cycloheptyl, (C ₁ -C ₂₀ alkyl) cyclooctyl, (C ₁ -C ₂₀ alkyl) adamantyl, (C ₁ -C ₂₀ alkyl) norbornenyl , (C ₁ -C ₂₀ alkyl) cyclopentenyl, (C ₁ -C ₂₀ alkyl) cyclohexenyl, (C ₁ -C ₂₀ alkyl) cycloheptenyl, (C ₁ -C ₂₀ alkyl) Group) bicyclo[1.1.1]pentyl, (C ₁ -C ₂₀ alkyl)bicyclo[2.1.1]hexyl, (C ₁ -C ₂₀ alkyl)bicyclo[2.2.1]heptyl, ( C ₁ -C ₂₀ alkyl) bicyclo[2.2.2] octyl, silolanyl group, phenyl, (C ₁ -C ₂₀ alkyl) phenyl, biphenyl, terphenyl Yl, naphthyl, 1,2,3,4-tetrahydronaphthyl, pyridyl, pyrimidinyl, or any combination thereof; each unsubstituted or substituted by cyclopentyl, cyclohexyl, cycloheptyl, ring Octyl, adamantyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2 .1]Heptyl, bicyclo[2.2.2]octyl, silyl, phenyl, (C ₁ -C ₂₀ alkyl) phenyl, biphenyl, terphenyl, naphthyl, 1 ,2,3,4-Tetrahydronaphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthene, benzo[9,10]phenanthryl, pyrenyl,

Group, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindyl Dolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, oxazolyl, phenanthroline Group, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, three Azinyl, dibenzofuranyl, dibenzothienyl, benzoxazolyl, dibenzoxazolyl, imidazopyridyl, imidazopyrimidinyl, azazylazolyl, azadibenzofuran Group, or azadibenzothienyl: deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , Hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C ₁ -C ₂₀ alkyl , Deuterium-containing C ₁ -C ₂₀ alkyl, fluorinated C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, Norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, two Cyclo[2.2.2]octyl, (C ₁ -C ₂₀ alkyl) cyclopentyl, (C ₁ -C ₂₀ alkyl) cyclohexyl, (C ₁ -C ₂₀ alkyl) cycloheptyl, (C ₁ -C ₂₀ alkyl) cyclooctyl, (C ₁ -C ₂₀ alkyl) adamantyl, (C ₁ -C ₂₀ alkyl) norbornenyl, (C ₁ -C ₂₀ alkyl) cyclopentenyl , (C ₁ -C ₂₀ alkyl) cyclohexenyl, (C ₁ -C ₂₀ alkyl) cycloheptenyl, (C ₁ -C ₂₀ alkyl) bicyclo [1.1.1] pentyl, (C _1- C ₂₀ alkyl)bicyclo[2.1.1]hexyl, (C ₁ -C ₂₀ alkyl)bicyclo[2.2.1]heptyl, (C ₁ -C ₂₀ alkyl)bicyclo[2.2.2 ]Octyl, silyl, phenyl, (C ₁ -C ₂₀ alkyl) phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, Fluorenyl, phenanthryl, anthracenyl, fluoranthene, benzo[9,10]phenanthryl, pyrenyl,

Group, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindyl Dolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, oxazolyl, phenanthroline Group, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, three Azinyl, dibenzofuranyl, dibenzothienyl, benzoxazolyl, dibenzoxazolyl, imidazopyridyl, imidazopyrimidinyl, azazylazolyl, azadibenzofuran Group, azadibenzothienyl, or any combination thereof; or -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -Ge(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ), -P(=O)(Q ₈ )(Q ₉ ), or -P(Q ₈ )(Q ₉ ), where R ₂₀ is neither Including fluorine groups and cyano groups, Q ₁ -Q ₉ may each independently be: -CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H, -CHDCDH ₂ , -CHDCD ₃ , -CD ₂ CD ₃ , -CD ₂ CD ₂ H or -CD ₂ CDH ₂ ; or N-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-amyl, neopentyl, isopentyl, sec, each unsubstituted or substituted as follows Pentyl, 3-pentyl, sec-isopentyl, phenyl, biphenyl, or naphthyl: deuterium, C ₁ -C ₂₀ alkyl, phenyl, or any combination thereof.

In one or more embodiments, R ₁ -R ₈ , R ₁₃ -R ₁₇ and R ₂₀ in Formula 1 may each independently be hydrogen, deuterium, -F, substituted or unsubstituted C ₁ -C ₂₀ Alkyl, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl, -Si(Q ₃ )(Q ₄ )(Q ₅ ) , Or -Ge(Q ₃ )(Q ₄ )(Q ₅ ). Here, R ₂₀ may include neither a fluorine group nor a cyano group.

In one or more embodiments, R ₁ -R ₈ and R ₁₃ -R ₁₇ in Formula 1 may each independently be: hydrogen, deuterium, or -F; each of C ₁ -C is unsubstituted or substituted as follows ₂₀ alkyl, C ₃ -C ₁₀ cycloalkyl, or C ₂ -C ₁₀ heterocycloalkyl: deuterium, -F, C ₁ -C ₂₀ alkyl, C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ Heterocycloalkyl, or any combination thereof; or -Si(Q ₃ )(Q ₄ )(Q ₅ ), or -Ge(Q ₃ )(Q ₄ )(Q ₅ ).

In one or more embodiments, R ₂₀ in Formula 1 may be: hydrogen or deuterium; C ₁ -C ₂₀ alkyl, C ₃ -C ₁₀ cycloalkyl, or C ₂ each unsubstituted or substituted as follows -C ₁₀ heterocycloalkyl: deuterium, C ₁ -C ₂₀ alkyl, C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl, or any combination thereof; or -Si(Q ₃ )( Q ₄ )(Q ₅ ), or -Ge(Q ₃ )(Q ₄ )(Q ₅ ).

The symbol d2 in Formula 1 represents the number of R ₂₀ , and may be an integer of 0-10. When d2 is 2 or greater, two or more R ₂₀ may be the same or different from each other. For example, d2 can be an integer from 0-6.

In one or more embodiments, at least one of R _{1 to} R ₈ in Formula 1 may include at least one fluorine group (-F).

In one or more embodiments, at least one of R _{1 to} R ₈ of Formula 1 may be a group including at least one fluorine group (-F).

In one or more embodiments, at least one of R ₁ -R ₈ in Formula 1 may each independently be: a fluorine group (-F); or a fluorinated C ₁ -C each unsubstituted or substituted as follows ₂₀ alkyl, fluorinated C ₃ -C ₁₀ cycloalkyl, or fluorinated C ₂ -C ₁₀ heterocycloalkyl: deuterium, C ₁ -C ₂₀ alkyl, C ₃ -C ₁₀ cycloalkyl, C _2- C ₁₀ heterocycloalkyl, or any combination thereof.

R ₁₈ and R _{19 in} Formula 1 may each independently be a substituted or unsubstituted C ₂ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl, substituted or unsubstituted C ₁ -C ₆₀ alkoxy, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenyl, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, or substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic groups.

基、吡咯基、噻吩基、呋喃基、咪唑基、吡唑基、噻唑基、異噻唑基、噁唑基、異噁唑基、吡啶基、吡嗪基、嘧啶基、噠嗪基、異吲哚基、吲哚基、吲唑基、嘌呤基、喹啉基、異喹啉基、苯並喹啉基、喹喔啉基、喹唑啉基、噌啉基、哢唑基、菲咯啉基、苯並咪唑基、苯並呋喃基、苯並噻吩基、異苯並噻唑基、苯並噁唑基、異苯並噁唑基、三唑基、四唑基、噁二唑基、三嗪基、二苯並呋喃基、二苯並噻吩基、苯並哢唑基、二苯並哢唑基、咪唑並吡啶基、咪唑並嘧啶基、氮雜哢唑基、氮雜二苯並呋喃基、氮雜二苯並噻吩基、或其任意組合。For example, R ₁₈ and R _{19 in} Formula 1 may each independently be: C ₂ -C ₂₀ alkyl or C ₁ -C ₂₀ alkoxy; C ₂ -C ₂₀ alkyl or C ₁ -each substituted as follows C ₂₀ Alkoxy: Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl, cyano , Nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C ₁ -C ₂₀ alkyl group, deuterium-containing C ₁ -C ₂₀ alkyl, fluorinated C ₁ -C ₂₀ alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornenyl, cyclopentenyl, cyclohexenyl , Cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, (C ₁ -C ₂₀ alkyl) cyclopentyl, (C ₁ -C ₂₀ alkyl) cyclohexyl, (C ₁ -C ₂₀ alkyl) cycloheptyl, (C ₁ -C ₂₀ alkyl) cyclooctyl, (C _1- C ₂₀ alkyl) adamantyl, (C ₁ -C ₂₀ alkyl) norbornenyl, (C ₁ -C ₂₀ alkyl) cyclopentenyl, (C ₁ -C ₂₀ alkyl) cyclohexenyl , (C ₁ -C ₂₀ alkyl) cycloheptenyl, (C ₁ -C ₂₀ alkyl) bicyclo [1.1.1] pentyl, (C ₁ -C ₂₀ alkyl) bicyclo [2.1.1] Hexyl, (C ₁ -C ₂₀ alkyl) bicyclo[2.2.1] heptyl, (C ₁ -C ₂₀ alkyl) bicyclo [2.2.2] octyl, silyl, phenyl, (C ₁ -C ₂₀ alkyl) phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, pyridyl, pyrimidinyl, or any combination thereof; or each Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo [1.1 .1]Pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, phenyl, (C ₁ -C ₂₀ alkyl)phenyl, Biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthene, benzo[9,10]phenanthryl, pyrenyl, Zyl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, iso Indolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, oxazolyl, phenanthroline Linyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, Triazinyl, dibenzofuranyl, dibenzothiol Phenyl, benzoxazolyl, dibenzoxazolyl, imidazopyridyl, imidazopyrimidinyl, azaazolyl, azadibenzofuranyl, or azadibenzothienyl: deuterium , -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl, cyano, nitro, amino, amidine Group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C ₁ -C ₂₀ alkyl group, deuterium-containing C ₁ -C ₂₀ alkyl group, Fluorinated C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornenyl, cyclopentenyl, cyclohexyl Alkenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, (C ₁ -C ₂₀ alkyl) cyclopentyl, (C ₁ -C ₂₀ alkyl) cyclohexyl, (C ₁ -C ₂₀ alkyl) cycloheptyl, (C ₁ -C ₂₀ alkyl) cyclooctyl, (C _1- C ₂₀ alkyl) adamantyl, (C ₁ -C ₂₀ alkyl) norbornenyl, (C ₁ -C ₂₀ alkyl) cyclopentenyl, (C ₁ -C ₂₀ alkyl) cyclohexyl Alkenyl, (C ₁ -C ₂₀ alkyl) cycloheptenyl, (C ₁ -C ₂₀ alkyl)bicyclo[1.1.1]pentyl, (C ₁ -C ₂₀ alkyl)bicyclo[2.1. 1] Hexyl, (C ₁ -C ₂₀ alkyl)bicyclo[2.2.1]heptyl, (C ₁ -C ₂₀ alkyl)bicyclo[2.2.2]octyl, silacyclopentane, benzene Group, (C ₁ -C ₂₀ alkyl) phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthene , Benzo[9,10]phenanthryl, pyrenyl,

Group, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindyl Dolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, oxazolyl, phenanthroline Group, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, three Azinyl, dibenzofuranyl, dibenzothienyl, benzoxazolyl, dibenzoxazolyl, imidazopyridyl, imidazopyrimidinyl, azazylazolyl, azadibenzofuran Group, azadibenzothienyl, or any combination thereof.

In one or more embodiments, R ₁₈ and R ₁₉ in Formula 1 may each independently be a substituted or unsubstituted C ₂ -C ₆₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₀ ring Alkyl, or substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl.

In one or more embodiments, R ₁₈ and R ₁₉ in Formula 1 may each independently be a C ₂ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, or C _2- C ₁₀ heterocycloalkyl: deuterium, -F, C ₁ -C ₂₀ alkyl, C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl, or any combination thereof.

For example, R ₁ -R ₈ and R ₁₃ -R _{17 in} Formula 1 may each independently be hydrogen, deuterium, -F, -CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a group represented by one of formulas 9-1 to 9-39, a group represented by one of formulas 9-1 to 9-39 in which at least one hydrogen is replaced by deuterium, wherein A group represented by one of formulae 9-1 to 9-39 in which at least one hydrogen is replaced by -F, a group represented by one of formulae 9-201 to 9-233, and a group in which at least one hydrogen is replaced by deuterium A group represented by one of 9-201 to 9-233, a group represented by one of formulas 9-201 to 9-233 in which at least one hydrogen is replaced by -F, one of formulas 10-1 to 10-126 A group represented by a group represented by one of formulas 10-1 to 10-126 in which at least one hydrogen is replaced by deuterium, a group represented by one of formulae 10-1 to 10-126 in which at least one hydrogen is replaced by -F A group represented by one of formulas 10-201 to 10-343, a group represented by one of formulas 10-201 to 10-343 in which at least one hydrogen is replaced by deuterium, in which at least one hydrogen is- The group represented by one of formulas 10-201 to 10-343, -Si(Q ₃ )(Q ₄ )(Q ₅ ), or -Ge(Q ₃ )(Q ₄ )(Q ₅ ) ( Here, Q ₃ -Q ₅ are the same as described in this specification), and at least one of R ₁ -R ₈ may be -F, -CF ₃ , -CF ₂ H, -CFH ₂ , and at least one hydrogen is -F A substituted group represented by one of formulas 9-1 to 9-39, a group represented by one of formulas 9-201 to 9-233 in which at least one hydrogen is replaced by -F, in which at least one hydrogen is replaced by -F The substituted group represented by one of formulas 10-1 to 10-126, or a group represented by one of formulas 10-201 to 10-343 in which at least one hydrogen is replaced by -F.

In one or more embodiments, R ₂₀ in Formula 1 may be hydrogen, deuterium, -CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , represented by one of formulas 9-1 to 9-39 A group, a group represented by one of formulae 9-1 to 9-39 in which at least one hydrogen is replaced by deuterium, a group represented by one of formulae 9-201 to 9-233, in which at least one hydrogen is replaced by deuterium A group represented by one of formulas 9-201 to 9-233, a group represented by one of formulas 10-1 to 10-126, and a group in which at least one hydrogen is replaced by deuterium by formulas 10-1 to 10-126 A group represented by one of formulas 10-201 to 10-343, a group represented by one of formulas 10-201 to 10-343 in which at least one hydrogen is replaced by deuterium, -Si( Q ₃ )(Q ₄ )(Q ₅ ), or -Ge(Q ₃ )(Q ₄ )(Q ₅ ) (here, Q ₃ -Q ₅ are the same as described in this specification).

。In one or more embodiments, R ₁₈ and R ₁₉ in Formula 1 may each independently be a group represented by one of Formulas 9-1 to 9-39, in which at least one hydrogen is replaced by deuterium by Formula 9- A group represented by one of 1 to 9-39, a group represented by one of formulas 9-1 to 9-39 in which at least one hydrogen is replaced by -F, a group represented by one of formulas 9-201 to 9-233 A group, a group represented by one of formulae 9-201 to 9-233 in which at least one hydrogen is replaced by deuterium, a group represented by one of formulae 9-201 to 9-233 in which at least one hydrogen is replaced by -F Group, a group represented by one of formulas 10-1 to 10-126, a group represented by one of formulas 10-1 to 10-126 in which at least one hydrogen is replaced by deuterium, in which at least one hydrogen is replaced by -F A group represented by one of formulas 10-1 to 10-126, a group represented by one of formulas 10-201 to 10-343, and a group in which at least one hydrogen is replaced by deuterium by formulas 10-201 to 10-343 A group represented by one or a group represented by one of formulas 10-201 to 10-343 in which at least one hydrogen is replaced by -F:

.

* In formulas 9-1 to 9-39, 9-201 to 9-233, 10-1 to 10-126, and 10-201 to 10-343 represents the binding site with adjacent atoms, Ph is a phenyl group, TMS is trimethylsilyl, and TMG is trimethylgermyl.

。"A group represented by one of formulae 9-1 to 9-39 in which at least one hydrogen is replaced by deuterium" and "a group represented by one of formulae 9-201 to 9-233 in which at least one hydrogen is replaced by deuterium""May each be a group represented by, for example, one of formulas 9-501 to 9-514 and 9-601 to 9-635:

.

。"A group represented by one of formulae 9-1 to 9-39 in which at least one hydrogen is replaced by -F" and "a group represented by one of formulae 9-201 to 9-233 in which at least one hydrogen is replaced by -F The group" may each be, for example, a group represented by one of formulas 9-701 to 9-710:

.

。"A group represented by one of formulae 10-1 to 10-126 in which at least one hydrogen is replaced by deuterium" and "a group represented by one of formulae 10-201 to 10-343 in which at least one hydrogen is replaced by deuterium""May each be a group represented by, for example, one of formulas 10-501 to 10-553:

.

。"A group represented by one of formulae 10-1 to 10-126 in which at least one hydrogen is replaced by -F" and "a group represented by one of formulae 10-201 to 10-343 in which at least one hydrogen is replaced by -F" The group" may each be, for example, a group represented by one of formulas 10-601 to 10-615:

.

In one or more embodiments, R ₄ -R Formula 1 is at least one (e.g., R ₄ -R ₈ one or two) of at least ₈ may include a fluoro group (-F). In one or more embodiments, in Formula 1, 1) R ₄ may include at least one fluorine group (-F); 2) R ₅ may include at least one fluorine group (-F); 3) R ₆ may Includes at least one fluorine group (-F); 4) R ₇ may include at least one fluorine group (-F); 5) R ₈ may include at least one fluorine group (-F); 6) R ₅ and R ₆ May each include at least one fluorine group (-F); 7) R ₅ and R ₇ may each include at least one fluorine group (-F); 8) R ₅ and R ₈ may each include at least one fluorine group (- F); 9) R ₆ and R ₇ may each include at least one fluorine group (-F); 10) R ₆ and R ₈ may each include at least one fluorine group (-F); or 11) R ₇ and R ₈ may each include at least one fluoro group (-F). In one or more embodiments, with respect to Formula 1, one or two of R ₁ -R ₈ may each independently include at least one fluorine group (-F), and at least one i) of R ₁ -R ₈ may not include The fluoro group (-F), and ii) may not be hydrogen.

In one or more embodiments, at least one of R ₁ and R ₃ in Formula 1 may not be hydrogen.

In one or more embodiments, R ₂₀ in Formula 1 may be a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, or a C ₂ -C ₁₀ heterocyclic ring each unsubstituted or substituted as follows Alkyl: deuterium, C ₁ -C ₂₀ alkyl, C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl, or any combination thereof.

In one or more embodiments, the formula 1 R ₂₀ may be unsubstituted or substituted with deuterium, C ₁ -C ₂₀ alkyl group, or any combination thereof C ₁ -C ₂₀ substituted alkyl.

In one or more embodiments, d2 in Formula 1 may be 2.

In one or more embodiments, the formula 1 R ₂₀ may be unsubstituted or substituted with deuterium, C ₁ -C ₂₀ alkyl group, or any combination thereof C ₁ -C ₂₀ substituted alkyl, and d2 may be 2 .

In one or more embodiments, the organometallic compound represented by Formula 1 may have at least one deuterium.

In one or more embodiments, at least one of R ₁ -R ₈ of Formula 1 may have at least one deuterium.

In one or more embodiments, at least one of R ₂₀ having the number d2 may have at least one deuterium.

In one or more embodiments, at least one of R ₂₀ in the number d2 may be a deuterium-containing C ₁ -C ₂₀ alkyl group or a deuterium-containing C ₃ -C ₁₀ cycloalkyl group that is unsubstituted or substituted as follows , Or C ₂ -C ₁₀ heterocycloalkyl containing deuterium: C ₁ -C ₂₀ alkyl, C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl, or any combination thereof.

In Formula 1, 1) Two or more of R ₁ -R ₈ may be optionally connected to each other to form a C ₅ -C ₃₀ carbocyclic group that is unsubstituted or substituted with at least one R _1a , or A C ₁ -C ₃₀ heterocyclic group that is unsubstituted or substituted with at least one R _1a , 2) two or more of R ₂₀ whose number is d2 may be optionally connected to each other to form an unsubstituted or substituted with at least one of R _1a C ₅ -C ₃₀ carbocyclic group, or an unsubstituted or substituted by at least one R _1a is C ₁ -C ₃₀ heterocyclic group, and 3) R ₁₃ -R ₁₉ of the two or more can be linked to form an optionally unsubstituted or substituted with at least one R _1a is C ₅ -C ₃₀ carbocyclic group with one another, or at least one unsubstituted or substituted C ₁ R _1a -C ₃₀ heterocyclic group. Here, R _1a can be understood by referring to the description of R ₂ .

基團、1,2,3,4-四氫萘基團、環戊二烯基團和芴基團。The term "C ₅ -C ₃₀ carbocyclic group" as used herein refers to a saturated or unsaturated cyclic group having only 5-30 carbon atoms as ring-forming atoms. The C ₅ -C ₃₀ carbocyclic group may be a monocyclic group or a polycyclic group. The term "(unsubstituted or substituted with at least one R _{1 a} ) C ₅ -C ₃₀ carbocyclic group" may include, for example, adamantyl groups each unsubstituted or substituted with at least one R _{1 a} , norbornyl Alkenyl group, bicyclo[1.1.1] pentane group, bicyclo[2.1.1] hexane group, bicyclo[2.2.1] heptyl group (norbornane group), bicyclo[ 2.2.2] Octyl group, cyclopentane group, cyclohexane group, cyclohexene group, phenyl group, naphthalene group, anthracene group, phenanthrene group, benzo[9,10] Phenanthrene group, pyrene group,

Group, 1,2,3,4-tetrahydronaphthalene group, cyclopentadiene group and fluorene group.

The term "C ₁ -C ₃₀ heterocyclic group" as used herein refers to having at least 1-30 carbon atoms selected from N, O, Si, P, Se, Ge, B and S A heteroatom is a saturated or unsaturated cyclic group as a ring atom. The C ₁ -C ₃₀ heterocyclic group may be a monocyclic group or a polycyclic group. "(Unsubstituted or substituted with at least one R _{1 a} ) C ₁ -C ₃₀ heterocyclic group" may include, for example, a thiophene group, a furan group, each unsubstituted or substituted with at least one R _{1 a} , Pyrrole group, silole group, borocyclopentadiene group, phosphocyclopentadiene group, selenophene group, germanocyclopentadiene group, benzothiophene group, benzofuran Group, indole group, indene group, benzosilole group, benzoborole group, benzophosphoryl group, benzoselenophene group, benzo Germanium group, dibenzothiophene group, dibenzofuran group, oxazole group, dibenzosilole group, dibenzoborole group, diphenyl Phosphorus group, dibenzoselenophene group, dibenzogermanium cyclopentadienyl group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group , Dibenzothiophene 5,5-dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, azaindenyl group, azabenzothiazole Group, azabenzoborole group, azabenzophosphoryl group, azabenzoselenophene group, azabenzogermanium group , Azadibenzothiophene group, azadibenzofuran group, azadiazole group, azafluorene group, azadibenzosilole group, azadibenzoboron heterocycle Pentadiene group, azadibenzophosphoryl group, azadibenzoselenophene group, azadibenzogermantocyclopentadiene group, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridine Azinyl group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrazole group, imidazole group, triazole group Group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole Azole group, benzothiazole group, benzoxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group and 5,6,7,8- Tetrahydroquinoline group.

The term "C ₁ -C ₆₀ alkyl" as used herein refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and non-limiting examples thereof include methyl, ethyl Group, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl and hexyl. The term "C ₁ -C ₆₀ alkylene" used herein refers to a divalent group having the same structure as that of a C ₁ -C ₆₀ alkyl group.

Non-limiting examples of C ₁ -C ₆₀ alkyl, C ₁ -C ₂₀ alkyl and/or C ₁ -C ₁₀ alkyl are each unsubstituted or substituted methyl, ethyl, n-propyl, Isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl, t-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, N-hexyl, isohexyl, sec-hexyl, t-hexyl, n-heptyl, isoheptyl, sec-heptyl, t-heptyl, n-octyl, isooctyl, sec-octyl, t-octyl, n-nonyl, isonon Base, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl and tert-decyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl Base, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl Base, isoheptyl, sec-heptyl, t-heptyl, n-octyl, isooctyl, s-octyl, t-octyl, n-nonyl, isononyl, s-nonyl, t-nonyl, n-decyl, Isodecyl, secondary decyl, tert-decyl, or any combination thereof. For example, Formula 9-33 may be a branched _C6 alkyl group, and may be a tert-butyl group substituted with two methyl groups.

The term "C ₁ -C ₆₀ alkoxy" as used herein refers to a monovalent group represented by -OA ₁₀₁ (wherein A ₁₀₁ is a C ₁ -C ₆₀ alkyl group), and examples thereof include methoxy, ethyl Oxy and isopropoxy. Non-limiting examples of C ₁ -C ₆₀ alkoxy, C ₁ -C ₂₀ alkoxy, or C ₁ -C ₁₀ alkoxy are methoxy, ethoxy, propoxy, butoxy and pentyl Oxy.

The term "C ₃ -C ₁₀ cycloalkyl" as used herein refers to a monovalent saturated hydrocarbon monocyclic group having 3-10 carbon atoms, and examples thereof include cyclopropyl, cyclobutyl, and cyclopentyl , Cyclohexyl and cycloheptyl. The term "C ₃ -C ₁₀ cycloalkylene" as used herein refers to a divalent group having the same structure as that of a C ₃ -C ₁₀ cycloalkyl group. Non-limiting examples of C ₃ -C ₁₀ cycloalkyl groups are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, bicyclo[1.1.1]pentyl , Bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl (norbornanyl) and bicyclo[2.2.2]octyl.

The term "C ₂ -C ₁₀ heterocycloalkyl" as used herein refers to having at least one heteroatom of N, O, P, Si, Se, Ge, B, or S as a ring-forming atom and 1-10 A monovalent saturated monocyclic group of three carbon atoms, and non-limiting examples thereof include tetrahydrofuranyl and tetrahydrothienyl. The term "C ₂ -C ₁₀ heterocycloalkylene" as used herein refers to a divalent group having the same structure as C ₂ -C ₁₀ heterocycloalkyl. Non-limiting examples of C ₂ -C ₁₀ heterocycloalkyl are silacyclopentane, silacyclohexyl, tetrahydrofuranyl, tetrahydro-2H-pyranyl, and tetrahydrothienyl.

The term "C ₂ -C ₆₀ alkenyl" as used herein refers to a hydrocarbon group formed by substituting at least one carbon-carbon double bond in the middle or end of a C ₂ -C ₆₀ alkyl group, and examples thereof include ethylene Group, propenyl and butenyl. The term "C ₂ -C ₆₀ alkenylene" as used herein refers to a divalent group having the same structure as that of a C ₂ -C ₆₀ alkenyl group.

The term "C ₂ -C ₆₀ alkynyl group" as used herein refers to a hydrocarbon group formed by substituting at least one carbon-carbon triple bond in the middle or terminal of a C ₂ -C ₆₀ alkyl group, and examples thereof include acetylene And propynyl. The term "C ₂ -C ₆₀ alkynylene" as used herein refers to a divalent group having the same structure as that of the C ₂ -C ₆₀ alkynyl group.

The term "C ₃ -C ₁₀ cycloalkenyl" as used herein refers to a monovalent monocyclic group that has 3-10 carbon atoms and at least one carbon-carbon double bond in its ring and does not have aromaticity, And non-limiting examples thereof include cyclopentenyl, cyclohexenyl and cycloheptenyl. The term "C ₃ -C ₁₀ cycloalkenylene" as used herein refers to a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkenyl group.

The term "C ₂ -C ₁₀ heterocycloalkenyl" as used herein refers to having at least one heteroatom selected from N, O, P, Si, Se, Ge, B, or S in its ring as a component A monovalent monocyclic group with ring atoms, 2-10 carbon atoms and at least one double bond. Examples of C ₁ -C ₁₀ heterocycloalkenyl groups are 2,3-dihydrofuryl and 2,3-dihydrothienyl. The term "C ₂ -C ₁₀ heterocycloalkenylene" as used herein refers to a divalent group having the same structure as the C ₂ -C ₁₀ heterocycloalkenyl group.

The term "C ₆ -C ₆₀ aryl group" as used herein refers to a monovalent group having a carbocyclic aromatic system having 6-60 carbon atoms, and the term "C ₆ -C ₆₀ "Arylene" refers to a divalent group having a carbocyclic aromatic system with 6-60 carbon atoms. Non-limiting examples of C ₆ -C ₆₀ aryl groups include phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, and eryl. When the C ₆ -C ₆₀ aryl group and the C ₆ -C ₆₀ arylene group each include two or more rings, the rings may be fused to each other.

The term "C ₇ -C ₆₀ alkaryl" as used herein refers to a C ₆ -C ₅₉ aryl group substituted with at least one C ₁ -C ₅₄ alkyl group.

The term "C ₁ -C ₆₀ heteroaryl" as used herein refers to a monovalent group having a cyclic aromatic system selected from the group consisting of N, O, P, Si, At least one heteroatom of Se, Ge, B, or S serves as a ring-forming atom and has 1-60 carbon atoms. The term "C ₁ -C ₆₀ heteroarylene" as used herein refers to a divalent group having a cyclic aromatic system selected from N, O, P, At least one heteroatom of Si, Se, Ge, B, or S serves as a ring-forming atom and has 1-60 carbon atoms. Examples of C ₁ -C ₆₀ heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. When the C ₆ -C ₆₀ heteroaryl group and the C ₆ -C ₆₀ heteroarylene group each include two or more rings, the rings may be fused to each other.

The term as used herein refers to a "C ₂ -C ₆₀ alkyl heteroaryl" is substituted with at least one C ₁ -C ₅₉ alkyl C ₁ -C ₅₉ heteroaryl group.

The term "C ₆ -C ₆₀ aryloxy" as used herein means -OA ₁₀₂ (wherein A ₁₀₂ is C ₆ -C ₆₀ aryl), and the term "C ₆ -C ₆₀ arylthio" as used herein "Means -SA ₁₀₃ (where A ₁₀₃ is a C ₆ -C ₆₀ aryl group).

The term "monovalent non-aromatic fused polycyclic group" as used herein refers to having two or more rings fused to each other, having only carbon atoms as ring-forming atoms, and in terms of its entire molecular structure A monovalent group that is not aromatic (for example, has 8-60 carbon atoms). Examples of the monovalent non-aromatic fused polycyclic group include a fluorenyl group. The term "divalent non-aromatic fused polycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic fused polycyclic group.

As used herein, the term "monovalent non-aromatic fused heteropolycyclic group" refers to having two or more rings that are fused to each other, in addition to carbon atoms, which are selected from N, O, P, A heteroatom of Si, Se, Ge, B, or S serves as a ring-forming atom, and is a monovalent group that does not have aromaticity in its entire molecular structure (for example, has 2-60 carbon atoms). Non-limiting examples of monovalent non-aromatic fused heteropolycyclic groups include oxazolyl. The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic fused heteropolycyclic group.

Substituted C ₅ -C ₃₀ carbocyclic group, substituted C ₁ -C ₃₀ heterocyclic group, substituted C ₁ -C ₆₀ alkyl, substituted C ₂ -C ₆₀ alkyl, substituted C ₂ -C ₆₀ alkenyl, substituted C ₂ -C ₆₀ alkynyl, substituted C ₁ -C ₆₀ alkoxy, substituted C ₃ -C ₁₀ cycloalkyl, substituted C ₂ -C ₁₀ heterocycloalkyl, substituted C ₃ -C ₁₀ cycloalkenyl, substituted C ₂ -C ₁₀ heterocycloalkenyl, substituted C ₆ -C ₆₀ aryl, substituted C ₇ -C ₆₀ alkaryl, substituted C ₆ -C ₆₀ aryl Oxy, substituted C ₆ -C ₆₀ arylthio group, substituted C ₁ -C ₆₀ heteroaryl group, substituted C ₂ -C ₆₀ alkyl heteroaryl group, substituted monovalent non-aromatic fused polycyclic group And the substituent of the substituted monovalent non-aromatic fused heteropolycyclic group can be: deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl group, or a C ₁ -C ₆₀ alkoxy; each unsubstituted or substituted with the following C ₁ -C ₆₀ alkyl , C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, or C ₁ -C ₆₀ alkoxy: deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, Phosphoric acid group or its salt, C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₂ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ Aryl, C ₇ -C ₆₀ alkylaryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl, C ₂ -C ₆₀ alkyl heteroaryl, Monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q ₁₁ )(Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ),- Ge(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -B(Q ₁₆ )(Q ₁₇ ), -P(=O)(Q ₁₈ )(Q ₁₉ ), -P(Q ₁₈ )(Q ₁₉ ) , Or any combination thereof; C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₂ -C ₁₀ heterocyclic ring each unsubstituted or substituted as follows Alkenyl, C ₆ -C ₆₀ aryl, C ₇ -C ₆₀ alkaryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl, C ₂ -C ₆₀ alkyl heteroaryl, monovalent non-aromatic Group fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt , C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₁ -C ₆₀ alkoxy, C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycle Alkyl, C ₃ -C ₁₀ cycloalkenyl, C ₂ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₇ -C ₆₀ alkaryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl, C ₂ -C ₆₀ alkyl heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ), -Ge(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ), -B(Q ₂₆ )(Q ₂₇ ), -P(=O)(Q ₂₈ )(Q ₂₉ ), -P(Q ₂₈ )(Q ₂₉ ), or any combination thereof; -N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ ) (Q ₃₄ )(Q ₃₅ ), -Ge(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -B(Q ₃₆ )(Q ₃₇ ), -P(=O)(Q ₃₈ )(Q ₃₉ ), Or -P(Q ₃₈ )(Q ₃₉ ); or any combination thereof.

In this specification, Q ₁ -Q ₉ , Q ₁₁ -Q ₁₉ , Q ₂₁ -Q ₂₉ and Q ₃₁ -Q ₃₉ may each independently be hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl ; Cyano group; nitro group; amidino group; hydrazine group; hydrazone group; carboxylic acid group or its salt; sulfonic acid group or its salt; phosphoric acid group or its salt; unsubstituted or deuterium, C _1- C ₆₀ alkyl, C ₆ -C ₆₀ aryl, or C ₁ -C ₆₀ alkyl substituted by any combination thereof; C ₂ -C ₆₀ alkenyl; C ₂ -C ₆₀ alkynyl; C ₁ -C ₆₀ alkoxy C ₃ -C ₁₀ cycloalkyl; C ₂ -C ₁₀ heterocycloalkyl; C ₃ -C ₁₀ cycloalkenyl; C ₂ -C ₁₀ heterocycloalkenyl; unsubstituted or deuterated, C ₁ -C ₆₀ alkyl, C ₆ -C ₆₀ aryl, or C ₆ -C ₆₀ aryl substituted by any combination thereof; C ₆ -C ₆₀ aryloxy; C ₆ -C ₆₀ arylthio; C ₁ -C ₆₀ heteroaryl; monovalent non-aromatic fused polycyclic group; or monovalent non-aromatic fused heteropolycyclic group.

For example, in this specification, Q ₁ -Q ₉ , Q ₁₁ -Q ₁₉ , Q ₂₁ -Q ₂₉ and Q ₃₁ -Q ₃₉ can each independently be: -CH ₃ , -CD ₃ , -CD ₂ H,- CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H, -CHDCDH ₂ , -CHDCD ₃ , -CD ₂ CD ₃ , -CD ₂ CD ₂ H, or -CD ₂ CDH ₂ ; or each of n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-butyl, unsubstituted or substituted as follows Pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, phenyl, biphenyl, or naphthyl: deuterium, C ₁ -C ₁₀ alkyl, Phenyl, or any combination thereof.

As used herein, the term "deuterium-containing C ₁ -C ₆₀ alkyl group (or deuterium-containing C ₁ -C ₂₀ alkyl group, deuterium-containing C ₂ -C ₂₀ alkyl group, etc.)" refers to a deuterium-containing A substituted C ₁ -C ₆₀ alkyl group (or a C ₁ -C ₂₀ alkyl group substituted with at least one deuterium, a C ₂ -C ₂₀ alkyl group substituted with at least one deuterium, etc.). For example, the term "deuterium-containing C ₁ alkyl (ie, deuterium-containing methyl)" as used herein includes -CD ₃ , -CD ₂ H, and -CDH ₂ .

The term "deuterium-containing C ₃ -C ₁₀ cycloalkyl" as used herein refers to a C ₃ -C ₁₀ cycloalkyl substituted with at least one deuterium. Examples of "deuterium-containing C ₃ -C ₁₀ cycloalkyl" include, for example, Formula 10-501.

As used herein, the term "fluorinated C ₁ -C ₆₀ alkyl (or fluorinated C ₁ -C ₂₀ alkyl etc.)", "fluorinated C ₃ -C ₁₀ cycloalkyl", or "fluorinated C ₂ -C ₁₀ heterocycloalkyl" refers to a C ₁ -C ₆₀ alkyl group (or C ₁ -C ₂₀ alkyl group, etc.) substituted by at least one fluoro group (-F), and at least one fluoro group ( -F) A substituted C ₃ -C ₁₀ cycloalkyl group and a C ₂ -C ₁₀ heterocycloalkyl group substituted with at least one fluoro group (-F). For example, the term "fluorinated C ₁ alkyl (ie, fluorinated methyl)" includes -CF ₃ , -CF ₂ H, and -CFH ₂ . "Fluorinated C ₁ -C ₆₀ alkyl (or fluorinated C ₁ -C ₂₀ alkyl, etc.)", "fluorinated C ₃ -C ₁₀ cycloalkyl", or "fluorinated C ₂ -C ₁₀ heterocycloalkane The “group” can be i) a fully fluorinated C ₁ -C ₆₀ alkyl group (or a fully fluorinated C ₁ -C ₂₀ alkyl group, etc.), fully fluorinated C ₁ -C ₆₀ alkyl groups in which all hydrogens in each are replaced by fluorine groups C ₃ -C ₁₀ cycloalkyl group, or fully fluorinated C ₂ -C ₁₀ heterocycloalkyl group, or ii) partially fluorinated C ₁ -C ₆₀ alkyl group in which some of the hydrogens in each are replaced by fluorine groups (Or partially fluorinated C ₁ -C ₂₀ alkyl, etc.), partially fluorinated C ₃ -C ₁₀ cycloalkyl, or partially fluorinated C ₂ -C ₁₀ heterocycloalkyl.

The term "(C ₁ -C ₂₀ alkyl)'X'group" as used herein refers to an'X' group substituted with at least one C ₁ -C ₂₀ alkyl group. For example, the term "(C ₁ -C ₂₀ alkyl)C ₃ -C ₁₀ cycloalkyl" as used herein refers to a C ₃ -C ₁₀ cycloalkyl substituted with at least one C ₁ -C ₂₀ alkyl group , And the term "(C ₁ -C ₂₀ alkyl)phenyl" as used herein refers to a phenyl group substituted with at least one C ₁ -C ₂₀ alkyl group. An example of (C ₁ alkyl)phenyl is tolyl.

The term "azaindole group, azabenzoborole group, azabenzophosphoryl group, azaindene group, azabenzosilole group, Azabenzogermantocyclopentadiene group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azapyrazole group, azadibenzo Borocyclopentadiene group, azadibenzophosphorene group, azafluorene group, azadibenzosilole group, azadibenzogermantocyclopentadiene Group, azadibenzothiophene group, azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluorene The -9-ketone group and the azadibenzothiophene 5,5-dioxide group" respectively refer to those in which at least one of the carbon atoms constituting the cyclic group is replaced by nitrogen and has an "indole group , Benzoborole group, benzophosphoryl group, indene group, benzosilole group, benzogermantole group, benzothiophene group , Benzoselenophene group, benzofuran group, oxazole group, dibenzoborole group, dibenzophosphoryl group, fluorene group, dibenzo Silole group, dibenzogermanium cyclopentadiene group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group and dibenzothiophene 5,5-dioxide group" the same skeleton heterocyclic group.

表示的基團可為由式CY1至CY88中的一者表示的基團：

在式CY1至CY88中， T₄ -T₈ 可各自獨立地為： 氟基團(-F)；或 各自未被取代或被如下取代的氟化C₁ -C₂₀ 烷基、氟化C₃ -C₁₀ 環烷基、或氟化C₂ -C₁₀ 雜環烷基：氘、C₁ -C₂₀ 烷基、C₃ -C₁₀ 環烷基、C₂ -C₁₀ 雜環烷基、或其任意組合； R₂ 、R₅ -R₈ 和R_1a 各自與以上描述的相同，並且R₂ 和R₅ -R₈ 可不為氫， *表示與式1中的Ir的結合位點， *"表示與式1中的相鄰原子的結合位點。In one or more embodiments, the formula 1 in

The represented group may be a group represented by one of formulas CY1 to CY88:

In formulas CY1 to CY88, T ₄ -T ₈ may each independently be: a fluorine group (-F); or a fluorinated C ₁ -C ₂₀ alkyl group, a fluorinated C ₃ group that is unsubstituted or substituted as follows -C ₁₀ cycloalkyl or fluorinated C ₂ -C ₁₀ heterocycloalkyl: deuterium, C ₁ -C ₂₀ alkyl, C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl, or Any combination thereof; R ₂ , R ₅ -R ₈ and R _1a are each the same as described above, and R ₂ and R ₅ -R ₈ may not be hydrogen, * indicates the binding site with Ir in formula 1, *" It represents the binding site with the adjacent atom in Formula 1.

For example, R ₂ and R ₅ -R ₈ in formulas CY1 to CY88 may each independently be: deuterium; or C ₁ -C ₂₀ alkyl, C ₃ -C ₁₀ cycloalkyl each unsubstituted or substituted as follows , Or C ₂ -C ₁₀ heterocycloalkyl: deuterium, C ₁ -C ₂₀ alkyl, C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl, or any combination thereof.

表示的基團可為由式A(1)至A(7)之一表示的基團：

在式A(1)至A(7)中， Y₂ 為C， X₂ 為O、S、N(R₂₅ )、C(R₂₅ )(R₂₆ )、或Si(R₂₅ )(R₂₆ )， R₉ -R₁₂ 和R₂₁ -R₂₆ 各自與關於R₂₀ 描述的相同， *'表示與式1中的Ir的結合位點，且 *"表示與式1中的相鄰原子的結合位點。In one or more embodiments, the formula 1 in

The represented group may be a group represented by one of formulas A(1) to A(7):

In formulas A(1) to A(7), Y ₂ is C, X ₂ is O, S, N(R ₂₅ ), C(R ₂₅ )(R ₂₆ ), or Si(R ₂₅ )(R ₂₆ ), R ₉ -R ₁₂ and R ₂₁ -R ₂₆ are each the same as described with respect to R ₂₀ , *'represents a binding site with Ir in Formula 1, and *" represents a binding to adjacent atoms in Formula 1 Site.

For example, R ₉ and R ₁₁ in the formula A(1) may each independently be a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, or a C ₂ -C ₁₀ heterocycloalkyl: deuterium, C ₁ -C ₂₀ alkyl, C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl, or any combination thereof.

In one or more embodiments, the Formula A R (1) ₉ and R ₁₁ may each independently be unsubstituted or deuterium, C ₁ -C ₂₀ alkyl group, or any combination of the substituted C ₁ - C ₂₀ alkyl.

In one or more embodiments, R ₁₀ and R ₁₂ in formula A(1) may each independently be hydrogen or deuterium.

In one or more embodiments, R ₉ and R ₁₁ in formula A(1) may be the same as each other.

In one or more embodiments, R ₉ and R ₁₁ in formula A(1) may be different from each other.

In one or more embodiments, R ₉ and R ₁₁ in Formula A(1) may be different from each other, and the number of carbons included in R ₁₁ may be greater than or equal to the number of carbons included in R ₉ .

In one or more embodiments, i) at least one of R _{9 to} R ₁₂ in formula A(1), ii) one of R _{21 to} R ₂₆ in formula A(2) and A(3), R ₁₁ , R ₁₂ , or any combination thereof, iii) one of R ₂₁ -R ₂₆ in formula A(4) and A(5), R ₉ , R ₁₂ , or any combination thereof, and iv) formula A(6) And one of R _{21 to} R ₂₆ in A(7), R ₉ , R ₁₀ , or any combination thereof, each may independently be a deuterium-containing C ₁ -C ₂₀ alkyl group that is unsubstituted or substituted as follows , C ₃ -C ₁₀ cycloalkyl containing deuterium, or C ₂ -C ₁₀ heterocycloalkyl containing deuterium: C ₁ -C ₂₀ alkyl, C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ hetero Cycloalkyl, or any combination thereof.

In one or more embodiments, the Formula A R (1) ₉ R ₁₁ and at least one (e.g., of formula A R (1) ₉ and R ₁₁₎ may each independently be unsubstituted or substituted with Deuterium-containing C ₁ -C ₂₀ alkyl group, deuterium-containing C ₃ -C ₁₀ cycloalkyl group, or deuterium-containing C ₂ -C ₁₀ heterocycloalkyl group substituted as follows: C ₁ -C ₂₀ alkyl group, C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl, or any combination thereof.

表示的基團可為由式A(1)或A(5)表示的基團。In one or more embodiments, the formula 1 in

The represented group may be a group represented by formula A(1) or A(5).

In one or more embodiments, R ₁₄ and R ₁₆ in Formula 1 may not be hydrogen.

For example, R ₁₃ , R ₁₄ , R ₁₆ and R _{17 in} Formula 1 may not be hydrogen.

In one or more embodiments, each of R ₁₃ , R ₁₄ , R ₁₆ and R ₁₇ in Formula 1 may include at least one carbon.

In one or more embodiments, in Formula 1, i) R ₁₃ and R ₁₇ may each independently be hydrogen or deuterium, and R ₁₄ and R ₁₆ may each independently be unsubstituted or substituted with at least one deuterium的 C ₁ -C ₂₀ alkyl group.

In one or more embodiments, in Formula 1, i) R ₁₃ and R ₁₇ may each independently be hydrogen or deuterium, and R ₁₄ and R ₁₆ may each independently be unsubstituted or substituted with at least one deuterium的 C ₂ -C ₂₀ alkyl group.

In one or more embodiments, R ₁₃ , R ₁₄ , R ₁₆ and R ₁₇ in Formula 1 may each independently be a C ₁ -C ₂₀ alkyl group that is unsubstituted or substituted with at least one deuterium.

In one or more embodiments, R ₁₃ , R ₁₄ , R ₁₆ and R ₁₇ in Formula 1 may each independently be a C ₂ -C ₂₀ alkyl group that is unsubstituted or substituted with at least one deuterium.

In one or more embodiments, the number of carbons included in the group represented by *-C(R ₁₃ )(R ₁₄ )(R ₁₉ ) in Formula 1 may be 5 or more, and/or Formula 1. The number of carbons included in the group represented by *-C(R ₁₆ )(R ₁₇ )(R ₁₈ ) in may be 5 or more.

In one or more embodiments, R ₁₃ , R ₁₄ and R ₁₉ of the group represented by *-C(R ₁₃ )(R ₁₄ )(R ₁₉ ) in Formula 1 may be connected to each other to form an unsubstituted at least one R _1a substituent or the C ₅ -C ₃₀ carbocyclic group, or an unsubstituted or substituted by at least one R _1a is C ₁ -C ₃₀ heterocyclic group. That is, the group represented by *-C(R ₁₃ )(R ₁₄ )(R ₁₉ ) in Formula 1 may be an unsubstituted or C ₅ -C ₃₀ carbocyclic group substituted with at least one R _1a , Or unsubstituted or substituted with at least one R _1a C ₁ -C ₃₀ heterocyclic group (for example, each unsubstituted or substituted with at least one R _{1 a} adamantyl group, norbornene group, two Cyclo[1.1.1] pentane group, bicyclo[2.1.1] hexane group, bicyclo[2.2.1]heptan group (norbornane group), bicyclo[2.2.2]octane Alkyl group, cyclopentyl group, cyclohexane group, or cyclohexene group).

In one or more embodiments, R ₁₆ , R ₁₇ and R ₁₈ of the group represented by *-C(R ₁₆ )(R ₁₇ )(R ₁₈ ) in Formula 1 may be connected to each other to form an unsubstituted at least one R _1a substituent or the C ₅ -C ₃₀ carbocyclic group, or an unsubstituted or substituted by at least one R _1a is C ₁ -C ₃₀ heterocyclic group. That is, the group represented by *-C(R ₁₆ )(R ₁₇ )(R ₁₈ ) in Formula 1 may be an unsubstituted or C ₅ -C ₃₀ carbocyclic group substituted with at least one R _1a , Or unsubstituted or substituted with at least one R _1a C ₁ -C ₃₀ heterocyclic group (for example, each unsubstituted or substituted with at least one R _{1 a} adamantyl group, norbornene group, two Cyclo[1.1.1] pentane group, bicyclo[2.1.1] hexane group, bicyclo[2.2.1]heptan group (norbornane group), bicyclo[2.2.2]octane Alkyl group, cyclopentyl group, cyclohexane group, or cyclohexene group).

化合物1至38中的TMS為三甲基甲矽烷基，且TMG為三甲基甲鍺烷基。For example, the organometallic compound may be one of the following compounds 1 to 38, but the embodiments of the present disclosure are not limited thereto.

TMS in compounds 1 to 38 is trimethylsilyl, and TMG is trimethylgermyl.

In the organometallic compound represented by Formula 1, 1) Ring A ₁ (see Formula 1') is a condensed ring group in which two phenyl groups are fused with one pyridine group as shown in Formula 1, And 2) At least one of R _{1 to} R ₈ includes at least one fluorine group (-F). Therefore, the transition dipole moment of the organometallic compound can be increased, and the conjugation length of the organometallic compound is relatively increased and the structural rigidity thereof is increased, resulting in a decrease in non-radiative transitions. Therefore, an electronic device including the organometallic compound represented by Formula 1, such as an organic light emitting device, may have high quantum efficiency, and therefore, may have high light emitting efficiency. [Formula 1']

In one or more embodiments, R ₁₈ and R ₁₉ in Formula 1 may each independently be a substituted or unsubstituted C ₂ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkene Group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl, substituted or unsubstituted C ₁ -C ₆₀ alkoxy, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl, Substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenyl, A substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted A substituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group. Therefore, the electron donating ability of ligand 2 in Formula 1 (see Formula 1') is improved, and therefore, the interaction between ligand 1 and ligand 2 in Formula 1 can be enhanced. Therefore, the organometallic compound represented by Formula 1 may have improved light-emitting transition characteristics, improved optical orientation (orientation) characteristics, and improved structural rigidity. Therefore, an electronic device including the organometallic compound represented by Formula 1, such as an organic light emitting device, may have high luminous efficiency and long lifetime.

In addition, since R ₂₀ in the organometallic compound represented by Formula 1 includes neither a fluorine group (-F) nor a cyano group, the organometallic compound represented by Formula 1 can emit light with high color purity ( For example, light having a relatively narrow half-width (FWHM) in the photoluminescence spectrum or the electroluminescence spectrum).

In one or more embodiments, the FWHM of the emission peak of the photoluminescence spectrum or electroluminescence spectrum of the organometallic compound may be 64 nm or less. For example, the FWHM of the emission peak of the photoluminescence spectrum or electroluminescence spectrum of the organometallic compound may be about 45 nm to about 64 nm, about 45 nm to about 59 nm, about 45 nm to about 55 nm, or about 50 nm. nm to about 55 nm.

In one or more embodiments, the maximum emission wavelength of the organic metal compound or photoluminescence spectra electroluminescence emission peak of the emission spectrum (emission peak wavelength, [lambda] _max) may be from about 615 nm to about 640 nm. In one or more embodiments, the maximum emission wavelength of the organic metal compound or photoluminescence spectra electroluminescence emission peak of the emission spectrum (emission peak wavelength, [lambda] _max) may be from about 615 nm to about 630 nm, or about 620 nm to about 630 nm.

The horizontal orientation ratio of the transition dipole moment of the organometallic compound represented by Formula 1 may be about 90% to about 100%.

For example, the horizontal orientation rate of the transition dipole moment of the organometallic compound may be, for example, about 91% to about 100%, about 92% to about 100%, about 93% to about 100%, about 94% to about 100%. , About 95% to about 100%, about 96% to about 100%, about 97% to about 100%, about 98% to about 100%, about 99% to about 100%, or about 100%.

The horizontal orientation rate of the transition dipole moment can be evaluated by using an angle-dependent photoluminescence (PL) measuring device. The angle-dependent PL measuring device can be understood by referring to the description of the angle-dependent PL measuring device disclosed in, for example, Korean Application No. 2013-0150834. Korean application No. 2013-0150834 is incorporated into this article.

As described above, since the horizontal orientation rate of the transition dipole moment of the organometallic compound is high, when the organic light-emitting device including the organometallic compound is driven, it can be substantially different from the film including the organometallic compound. The electric field is emitted parallel to the upper side, and therefore, the light loss caused by the waveguide mode and/or the surface plasmon polariton mode can be reduced. Due to the high external extraction efficiency of electronic devices that emit light by such a mechanism (ie, from electronic devices (eg, organic light-emitting devices) that include a film containing the organometallic compound (eg, an emission layer that will be described) ) The efficiency of extracting light to the outside), electronic devices including the organometallic compound, such as organic light-emitting devices, may have high luminous efficiency.

The photoluminescence quantum yield of the organometallic compound represented by Formula 1 in the film may be about 90% to about 100%. For example, the PLQY of the organometallic compound in the film may be about 91% to about 100%, about 92% to about 100%, about 93% to about 100%, about 94% to about 100%, about 95% to about 95%. About 100%, about 96% to about 100%, about 97% to about 100%, about 98% to about 100%, or about 99% to about 100%, or about 100%.

In one or more embodiments, the PLQY of the organometallic compound in the film may be about 95% to about 99%, about 96% to about 99%, about 97% to about 99%, or about 98% to about 99%.

The method of measuring PLQY in the film can be understood by referring to Evaluation Example 1.

The synthesis method of the organometallic compound represented by Formula 1 can be understood by those of ordinary skill in the art by referring to the synthesis examples provided below.

The organometallic compound represented by Formula 1 is suitable for use in an organic layer of an organic light emitting device, for example, suitable for use as a dopant in an emission layer of the organic layer. Therefore, another aspect provides an organic light emitting device, which includes: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic layer At least one organometallic compound represented by Formula 1 is included.

Since the organic light emitting device includes an organic layer including the organometallic compound represented by Formula 1, it is excellent in driving voltage, external quantum efficiency, relatively narrow FWHM of electroluminescence (EL) spectral emission peak, and lifetime. Characteristics.

The organometallic compound of Formula 1 may be used between a pair of electrodes of an organic light emitting device. For example, the organometallic compound represented by Formula 1 may be included in the emission layer. In this regard, the organometallic compound may act as a dopant, and the emission layer may further include a host (ie, the amount of the organometallic compound represented by Formula 1 in the emission layer is less than the amount of the host ).

In one or more embodiments, the emission layer may emit red light.

The expression "(organic layer) includes at least one organometallic compound" used herein may include the case where "(organic layer) includes the same organometallic compound represented by Formula 1" and where "(organic layer) includes two or There are more different organometallic compounds represented by Formula 1."

For example, the organic layer may include only Compound 1 as the organometallic compound. In this regard, Compound 1 may be present in the emission layer of the organic light emitting device. In one or more embodiments, the organic layer may include compound 1 and compound 2 as the organometallic compound. In this regard, Compound 1 and Compound 2 may exist in the same layer (for example, both Compound 1 and Compound 2 may exist in the emission layer).

The first electrode may be an anode as a hole injection electrode, and the second electrode may be a cathode as an electron injection electrode, or the first electrode may be a cathode as an electron injection electrode, and the second electrode The electrode may be an anode as a hole injection electrode.

In one or more embodiments, in the organic light-emitting device, the first electrode is an anode, and the second electrode is a cathode, and the organic layer is further included in the first electrode and the emitting device. The hole transport area between the layers and the electron transport area between the emission layer and the second electrode, and the hole transport area includes a hole injection layer, a hole transport layer, an electron blocking layer, or Any combination thereof, and the electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

The term "organic layer" as used herein refers to a single layer or multiple layers between the first electrode and the second electrode of the organic light emitting device. In addition to organic compounds, the "organic layer" may also include organometallic composites containing metals.

FIG. 1 is a schematic diagram of an organic light emitting device 10 according to an embodiment. Hereinafter, the structure of the organic light emitting device according to the embodiment and the method of manufacturing the organic light emitting device according to the embodiment will be described with respect to FIG. 1. The organic light emitting device 10 includes a first electrode 11, an organic layer 15 and a second electrode 19 that are sequentially stacked.

A substrate may be additionally provided below the first electrode 11 or above the second electrode 19. For use as the substrate, any substrate used in general organic light-emitting devices may be used, and the substrate may each have excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance. Glass substrate or transparent plastic substrate.

In one or more embodiments, the first electrode 11 may be formed by depositing or sputtering a material for forming the first electrode 11 on the substrate. The first electrode 11 may be an anode. The material used to form the first electrode 11 may include a material having a high work function to promote hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode or a transmissive electrode. The material used to form the first electrode 11 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), or zinc oxide (ZnO). In one or more embodiments, the material used to form the first electrode 11 may be a metal such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg -In) or magnesium-silver (Mg-Ag).

The first electrode 11 may have a single-layer structure or a multilayer structure including two or more layers. For example, the first electrode 11 may have a three-layer structure of ITO/Ag/ITO.

The organic layer 15 is located on the first electrode 11.

The organic layer 15 may include a hole transport area, an emission layer, and an electron transport area.

The hole transmission region may be between the first electrode 11 and the emission layer.

The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.

The hole transmission area may include only a hole injection layer or a hole transmission layer. In one or more embodiments, the hole transport region may have a hole injection layer/hole transport layer structure or a hole injection layer/hole transport layer/electron blocking layer structure, which starts from the first electrode 11 The order of the statements are stacked sequentially.

When the hole transport region includes a hole injection layer (HIL), the hole injection layer may be formed by using one or more suitable methods such as vacuum deposition, spin coating, casting, and/or Langmuir-Brow Jeter (LB) is deposited and formed on the first electrode 11.

When the hole injection layer is formed by vacuum deposition, the deposition conditions may be changed according to the material used to form the hole injection layer and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature of about 100°C to about 500°C, a vacuum pressure of about ^10-8 Torr to about ^10-3 Torr, and a deposition rate of about 0.01 Å/sec to about 100 Å/sec. However, the deposition conditions are not limited to this,

When spin coating is used to form the hole injection layer, coating conditions may vary according to the material used to form the hole injection layer and the structure and thermal properties of the hole injection layer. For example, the coating speed may be about 2,000 rpm to about 5,000 rpm, and the temperature at which heat treatment is performed to remove the solvent after coating may be about 80°C to about 200°C. However, the coating conditions are not limited to this.

By referring to the conditions for forming the hole injection layer, the conditions for forming the hole transport layer and the electron blocking layer can be understood.

[式201]

[式202]

式201中的Ar₁₀₁ 和Ar₁₀₂ 可各自獨立地為各自未被取代或被如下取代的亞苯基、亞並環戊二烯基、亞茚基、亞萘基、亞薁基、亞庚搭烯基、亞苊基、亞芴基、亞非那烯基、亞菲基、亞蒽基、亞熒蒽基、亞苯並[9,10]菲基、亞芘基、亞䓛基、亞並四苯基、亞

基、亞苝基、或亞並五苯基：氘、-F、-Cl、-Br、-I、羥基、氰基、硝基、氨基、脒基、肼基、腙基、羧酸基團或其鹽、磺酸基團或其鹽、磷酸基團或其鹽、C₁ -C₆₀ 烷基、C₂ -C₆₀ 烯基、C₂ -C₆₀ 炔基、C₁ -C₆₀ 烷氧基、C₃ -C₁₀ 環烷基、C₃ -C₁₀ 環烯基、C₂ -C₁₀ 雜環烷基、C₂ -C₁₀ 雜環烯基、C₆ -C₆₀ 芳基、C₆ -C₆₀ 芳氧基、C₆ -C₆₀ 芳硫基、C₁ -C₆₀ 雜芳基、單價非芳族稠合多環基團、單價非芳族稠合雜多環基團、或其任意組合。The hole transmission region may include m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4 ''-Tris(N-oxazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzene sulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly (4-sulfostyrene) (PEDOT/PSS), polyaniline/camphorsulfonic acid (PANI/CSA), polyaniline/poly(4-sulfostyrene) (PANI/PSS), a compound represented by the following formula 201, The compound represented by the following formula 202, or any combination thereof:

[Eq. 201]

[Eq. 202]

Ar ₁₀₁ and Ar _{102 in} formula 201 may each independently be a phenylene group, a cyclopentadienylene group, an indenylene group, a naphthylene group, azulenylene group, and a heptylene group which are each unsubstituted or substituted as follows Alkenyl, acenaphthylene, fluorenylene, phenalenylene, phenanthrylene, anthracenylene, fluoranthene, benzo[9,10]phenanthrylene, pyrenylene, pyrene, sub Tetraphenyl, ethylene

Group, perylene, or pentaphenyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group Or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₁ -C ₆₀ alkoxy Group, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₂ -C ₁₀ heterocycloalkyl, C ₂ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, or random combination.

The symbols xa and xb in formula 201 may each independently be an integer of 0-5, or 0, 1, or 2. For example, xa may be 1 and xb may be 0, but xa and xb are not limited thereto.

R ₁₀₁ -R ₁₀₈ , R ₁₁₁ -R ₁₁₉ and R ₁₂₁ -R _{124 in} formulas 201 and 202 may each independently be: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, Nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C ₁ -C ₁₀ alkyl (for example, methyl, Ethyl, propyl, butyl, pentyl, or hexyl), or C ₁ -C ₁₀ alkoxy (for example, methoxy, ethoxy, propoxy, butoxy, or pentoxy); C ₁ -C ₁₀ alkyl group or C ₁ -C ₁₀ alkoxy group each unsubstituted or substituted as follows: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, Amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, or any combination thereof; or each unsubstituted or substituted phenyl group, Naphthyl, anthracenyl, fluorenyl, or pyrenyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group Or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₁₀ alkyl group, or a C ₁ -C ₁₀ alkoxy group, or any combination thereof.

R _{109 in} formula 201 can be phenyl, naphthyl, anthryl, or pyridyl, each unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro Group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkane Oxy, phenyl, naphthyl, anthryl, pyridyl, or any combination thereof.

式201A中的R₁₀₁ 、R₁₁₁ 、R₁₁₂ 和R₁₀₉ 可通過參照本文中提供的描述而理解。In one or more embodiments, the compound represented by Formula 201 may be represented by Formula 201A: [Formula 201A]

R ₁₀₁ , R ₁₁₁ , R ₁₁₂ and R _{109 in} Formula 201A can be understood by referring to the description provided herein.

所述電洞傳輸區域的厚度可在約100Å至約10,000Å、例如約100Å至約1,000Å的範圍內。當所述電洞傳輸區域包括電洞注入層、電洞傳輸層、或其組合時，所述電洞注入層的厚度可在約100Å至約10,000Å、例如約100Å至約1,000Å的範圍內，且所述電洞傳輸層的厚度可在約50Å至約2,000Å、例如約100Å至約1,500Å的範圍內。當所述電洞傳輸區域、電洞注入層和電洞傳輸層的厚度在這些範圍內時，可獲得令人滿意的電洞傳輸特性而沒有驅動電壓的顯著增加。For example, the hole transmission area may include one of compounds HT1 to HT21 or any combination thereof:

The thickness of the hole transmission region may be in the range of about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, or a combination thereof, the thickness of the hole injection layer may be in the range of about 100Å to about 10,000Å, for example, about 100Å to about 1,000Å And the thickness of the hole transport layer may be in the range of about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thickness of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics can be obtained without a significant increase in driving voltage.

In addition to these materials, the hole transport region may further include charge generation materials for improving conductivity. The charge generation material may be uniformly or non-uniformly dispersed in the hole transport region.

The charge generating material may be, for example, a p-dopant. The p-dopant may be a quinone derivative, a metal oxide, a compound containing a cyano group, or any combination thereof, but the embodiments of the present disclosure are not limited thereto. Examples of the p-dopant are quinone derivatives such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4- TCNQ), or F6-TCNNQ; metal oxides such as tungsten oxide or molybdenum oxide; compounds containing cyano groups such as the following compound HT-D1; or any combination thereof.

The hole transmission area may include a buffer layer.

Also, the buffer layer may compensate for an optical resonance distance according to the wavelength of light emitted from the emission layer, and therefore, the efficiency of the formed organic light emitting device may be improved.

Meanwhile, when the hole transport region includes an electron blocking layer, the material used for the electron blocking layer may be the material used for the hole transport region described above, the material used for the host, which will be described later , Or any combination thereof. However, when the hole transport region includes an electron blocking layer, the material used for the electron blocking layer may be mCP, compound HT21, or any combination thereof, which will be described later.

Then, an emission layer (EML) may be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, or the like. When the emissive layer is formed by vacuum deposition or spin coating, although the deposition or coating conditions may be changed according to the material used to form the emissive layer, the deposition or coating conditions may be the same as those used to form the hole injection Similar to those applied when layering.

The emission layer may include a host and a dopant, and the dopant may include the organometallic compound represented by Formula 1 described herein.

。The host may include TPBi, TBADN, ADN (also referred to as "DNA"), CBP, CDBP, TCP, mCP, compound H50, compound H51, compound H52, or any combination thereof:

.

When the organic light emitting device is a full-color organic light emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer. In one or more embodiments, due to a stack structure including a red emission layer, a green emission layer, and/or a blue emission layer, the emission layer may emit white light.

When the emission layer includes a host and a dopant, based on 100 parts by weight of the host, the amount of the dopant may be in the range of about 0.01 parts by weight to about 15 parts by weight, but the implementation of the present disclosure The way is not limited to this.

The thickness of the emission layer may range from about 100 Å to about 1,000 Å, for example, from about 200 Å to about 600 Å. When the thickness of the emission layer is within this range, excellent light emission characteristics can be obtained without a significant increase in driving voltage.

Then, the electron transport region may be located on the emission layer.

The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

For example, the electron transport region may have a hole blocking layer/electron transport layer/electron injection layer structure or an electron transport layer/electron injection layer structure, but the structure of the electron transport region is not limited thereto. The electron transport layer may have a multilayer structure or a single layer structure including two or more different materials.

The conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer constituting the electron transport region can be understood by referring to the conditions for forming the hole injection layer.

When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of BCP, Bphen, and BAlq.

In one or more embodiments, the hole blocking layer may include the host, a material for forming an electron transport layer to be described later, a material for forming an electron injection layer to be described later, or random combination.

The thickness of the hole blocking layer may be in the range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 600 Å. When the thickness of the hole blocking layer is within these ranges, the hole blocking layer may have excellent hole blocking characteristics without a significant increase in driving voltage.

The electron transport layer may include BCP, Bphen, TPBi, Alq ₃ , BAlq, TAZ, NTAZ or any combination thereof:

。In one or more embodiments, the electron transport layer may include one of compounds ET1 to ET25 or any combination thereof:

.

The thickness of the electron transport layer may be in the range of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory electron transport characteristics without a significant increase in driving voltage.

Moreover, in addition to the materials described above, the electron transport layer may further include a material containing metal.

The metal-containing material may include Li composite. The Li complex may include, for example, the compound ET-D1 or ET-D2.

The electron transport region may include an electron injection layer (EIL) that facilitates the flow of electrons from the second electrode 19 therein.

The electron injection layer may include LiF, NaCl, CsF, Li ₂ O, BaO, or any combination thereof.

The thickness of the electron injection layer may range from about 1 Å to about 100 Å and, for example, from about 3 Å to about 90 Å. When the thickness of the electron injection layer is within the above-described range, the electron injection layer may have satisfactory electron injection characteristics without a significant increase in driving voltage.

The second electrode 19 may be located on the organic layer 15. The second electrode 19 may be a cathode. The material used to form the second electrode 19 may be a metal, an alloy, a conductive compound, or any combination thereof having a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In) or magnesium-silver (Mg-Ag) can be used As a material for forming the second electrode 19. In order to manufacture a top emission type light emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.

In the foregoing, the organic light emitting device has been described with reference to FIG. 1, but the embodiments of the present disclosure are not limited thereto.

Hereinafter, the compound and the organic light-emitting device according to the embodiment are described in detail with reference to synthesis examples and examples. However, the organic light emitting device is not limited thereto. The wording "use B instead of A" used in describing the synthesis examples means that the amount of B used is the same as the amount of A used in terms of Mohr equivalent. Example

中間物 L4-4 的合成 Synthesis Example 1 (Compound 4 )

Synthesis of intermediate L4-4

Mix 5 g (20.9 mmol) of 2-chloro-4-iodopyridine with 50 ml of anhydrous THF, and slowly add 12.5 ml (25 mmol) of 2.0 M diisopropylamino to it at a temperature of -78°C Lithium (in THF). After about 3 hours, 2.5 ml (32 mmol) of ethyl formate was slowly added dropwise thereto, and then, the resulting mixture was stirred at room temperature for 18 hours. Water and ethyl acetate were added to the reaction mixture to extract the organic layer, and then the organic layer was dried by using magnesium sulfate, followed by distillation under reduced pressure and purification using liquid chromatography to obtain 2.2 g (40% of Yield) intermediate L4-4. LC-MS m/z = 769.48 (M+H) ⁺ Synthesis of intermediate L4-3

Mix 1.9 g (7.2 mmol) of intermediate L4-4 with 60 ml of acetonitrile and 15 ml of water, and then add 0.4 g (0.5 mmol) PdCl ₂ (PPh ₃ ) ₂ , 1.0 g (7.2 mmol) 3-fluoro Phenylboronic acid and 2.5 g (18.0 mmol) K ₂ CO ₃ , and then, the mixture was heated while refluxing at a temperature of 80° C. for 18 hours. The reaction mixture was concentrated under reduced pressure, and dichloromethane and water were added thereto to extract the organic layer, and then the organic layer was dried by using magnesium sulfate, followed by distillation under reduced pressure and using liquid chromatography Purified to obtain 1.4 g (78% yield) of intermediate L4-3. LC-MS m/z = 236(M+H) ⁺ Synthesis of intermediate L4-2

Mix 5.4 g (15.8 mmol) (methoxymethyl)triphenylphosphonium chloride with 50 ml of anhydrous ether, then add 16 ml of 1.0 M potassium tert-butoxide solution (in THF) to it dropwise, and The mixture was stirred at room temperature for about 1 hour. After that, 1.5 g (6.3 mmol) of Intermediate L4-3 mixed with 30 ml of anhydrous THF was slowly added dropwise thereto, and the resulting mixture was stirred at room temperature for 18 hours. Water and ethyl acetate were added to the reaction mixture to extract the organic layer, and then the organic layer was dried by using magnesium sulfate, followed by distillation under reduced pressure and purification using liquid chromatography to obtain 1.6 g (95% of Yield) of intermediate L4-2. Synthesis of LC-MS m / z = 264 (M + H) + Intermediate is L4- 1

1.4 g (5.1 mmol) of Intermediate L4-2 was mixed with 40 ml of dichloromethane, and 3.0 ml of methanesulfonic acid was slowly added dropwise thereto, and then, the resulting mixture was stirred at room temperature for about 18 hours. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture to extract the organic layer, and then the organic layer was dried by using magnesium sulfate, followed by distillation under reduced pressure and purification using liquid chromatography to obtain 1.0 g (90 % Yield) of the intermediate L4-1. LC-MS m/z = 232(M+H) ⁺ synthesis of intermediate L4

1.0 g (4.1 mmol) intermediate L4-1 was mixed with 40 ml THF and 10 ml water, 0.9 g (6.2 mmol) 3,5-dimethylphenylboronic acid, 0.09 g (0.4 mmol) Pd( OAc) ₂ , 0.35 g (0.82 mmol) Sphos, and 1.4 g (10.3 mmol) K ₂ CO ₃ , and the mixture was heated while refluxing. Ethyl acetate and water were added to the reaction mixture to extract the organic layer, and then the organic layer was dried by using magnesium sulfate, followed by distillation under reduced pressure and purification using liquid chromatography to obtain 1.1 g (85% of Yield) of intermediate L4. LC-MS m/z = 302(M+H) ⁺ Synthesis of intermediate L4 Dimer ( L4 Dimer )

40 ml of ethoxyethanol and 15 ml of distilled water were mixed with 1.05 g (3.4 mmol) of intermediate L4 and 0.6 g (1.6 mmol) of iridium chloride, and then, the mixture was heated while refluxing for 24 hours. The temperature of the reaction mixture was lowered to room temperature to obtain a solid product, and then the solid product was filtered and washed sequentially by using water, methanol, and hexane. The resulting solid was dried in a vacuum oven to obtain 1.1 g of intermediate L4 Dimer. Synthesis of compound 4

Combine 1.0 g (0.63 mmol) intermediate L4 Dimer, 0.9 g (4.5 mmol) 3,7-diethyl-3,7-dimethylnonane-4,6-dione and 0.48 g (4.5 mmol) Na ₂ CO _{3 was} mixed with 40 ml of ethoxyethanol, and then the mixture was stirred at 90°C for 24 hours. The reaction mixture was cooled to room temperature to obtain a solid product, which was then filtered and purified by liquid chromatography to obtain 1.0 g (80% yield) of Compound 4. LC-MS m/z = 1035(M+H) ⁺

中間物 L1-2 的合成 Synthesis Example 2 (Compound 1 )

Synthesis of intermediate L1-2

Mix 6.0 g (23.7 mmol) 2-chloro-4-iodo-3-methylpyridine with 80 ml acetonitrile and 20 ml water, and then add 1.2 g (1.6 mmol) PdCl ₂ (PPh ₃ ) ₂ , 4.4 g (26.1 mmol) (3-fluoro-2-methanylphenyl)boronic acid and 8.2 g (59.2 mmol) K ₂ CO ₃ , and the resulting mixture was heated at a temperature of 80° C. while refluxing for 18 hours. The reaction mixture was concentrated under reduced pressure, and ethyl acetate and water were added thereto to extract the organic layer, and then the organic layer was dried by using magnesium sulfate, followed by distillation under reduced pressure and using liquid chromatography Purified to obtain 5.0 g (85% yield) of intermediate L1-2. LC-MS m/z = 250(M+H) ⁺ Synthesis of intermediate L1-1

4.0 g (16.0 mmol) of intermediate L1-2 was dissolved in 150 ml of anhydrous N,N-dimethylformamide, and then, 19 ml (19.2 mmol) of 1.0 M in THF was slowly added dropwise to it Potassium tert-butoxide solution, then, the reaction mixture was heated at a temperature of 80°C for 6 hours. Once the reaction was completed, ethyl acetate and water were added thereto to extract the organic layer, and then the organic layer was dried by using magnesium sulfate. The reaction mixture was filtered, concentrated under reduced pressure, and then, purified by liquid chromatography to obtain 1.3 g (35% yield) of intermediate L1-1. LC-MS m/z = 232(M+H) ⁺ synthesis of intermediate L1

1.4 g (85% yield) of Intermediate L1 was prepared in the same manner as used for the synthesis of Intermediate L4 of Synthesis Example 1, except for the following: Intermediate L1-1 was used instead of Intermediate L4-1. LC-MS m/z = 303(M+H) ⁺ Synthesis of intermediate L1 Dimer

The intermediate L1 Dimer was prepared in the same manner as the L4 Dimer used in the synthesis of Synthesis Example 1, except that the intermediate L1 was used instead of the intermediate L4. Synthesis of compound 1

0.6 g (47% yield) of Compound 1 was prepared in the same manner as used for the synthesis of Compound 4 of Synthesis Example 1, except for the following: Intermediate L1 Dimer was used instead of Intermediate L4 Dimer. LC-MS m/z = 1035(M+H) ⁺

中間物 L6-3 的合成 Synthesis Example 3 (Compound 6 )

Synthesis of intermediate L6-3

2.5 g (73% yield) of Intermediate L6-3 was prepared in the same manner as used for the synthesis of Intermediate L4-3 of Synthesis Example 1, except that: 3-(trifluoromethyl)benzene was used Boronic acid replaces 3-fluorophenylboronic acid. LC-MS m/z = 286(M+H) ⁺ Synthesis of intermediate L6-2

2.7 g (99% yield) of Intermediate L6-2 was prepared in the same manner as used for the synthesis of Intermediate L4-2 of Synthesis Example 1, except for the following: Intermediate L6-3 was used instead of Intermediate L4 -3. LC-MS m/z = 314(M+H) ⁺ Synthesis of intermediate L6-1

1.1 g (45% yield) of Intermediate L6-1 was prepared in the same manner as used for the synthesis of Intermediate L4-1 of Synthesis Example 1, except for the following: Intermediate L6-2 was used instead of Intermediate L4 -2. LC-MS m/z = 282(M+H) ⁺ synthesis of intermediate L6

1.1 g of Intermediate L6 (80% yield) was prepared in the same manner as used for the synthesis of Intermediate L4 of Synthesis Example 1, except for the following: Intermediate L6-1 was used instead of Intermediate L4-1. LC-MS m/z = 352(M+H) ⁺ Synthesis of intermediate L6 Dimer

Intermediate L6 Dimer was prepared in the same manner as used to synthesize Intermediate L4 Dimer of Synthesis Example 1, except for the following: Intermediate L6 was used instead of Intermediate L4. Synthesis of compound 6

0.7 g (43% yield) of compound 6 was prepared in the same manner as used for the synthesis of compound 4 of Synthesis Example 1, except for the following: intermediate L6 Dimer and 3,3,7,7-tetra Methylnonane-4,6-dione replaces the intermediate L4 Dimer and 3,7-diethyl-3,7-dimethylnonane-4,6-dione. LC-MS m/z = 1107(M+H) ⁺

中間物 L7-3 的合成 Synthesis Example 4 ( Compound 7 )

Synthesis of intermediate L7-3

1.8 g (70% yield) of Intermediate L7-3 was prepared in the same manner as used for the synthesis of Intermediate L4-3 of Synthesis Example 1, except for the following: 3-(trifluoromethyl)- 4-methylphenylboronic acid replaces 3-fluorophenylboronic acid. LC-MS m/z = 300(M+H) ⁺ Synthesis of intermediate L7-2

1.8 g (95% yield) of Intermediate L7-2 was prepared in the same manner as used for the synthesis of Intermediate L4-2 of Synthesis Example 1, except for the following: Intermediate L7-3 was used instead of Intermediate L4 -3. LC-MS m/z = 328(M+H) ⁺ Synthesis of intermediate L7-1

0.8 g (40% yield) of Intermediate L7-1 was prepared in the same manner as used for Synthesis of Intermediate L4-1 of Synthesis Example 1, except for the following: Intermediate L7-2 was used instead of Intermediate L4 -2. LC-MS m/z = 296(M+H) ⁺ Synthesis of intermediate L7

0.8 g (90% yield) of Intermediate L7 was prepared in the same manner as used for the synthesis of Intermediate L4 of Synthesis Example 1, except for the following: Intermediate L7-1 was used instead of Intermediate L4-1. LC-MS m/z = 366(M+H) ⁺ Synthesis of intermediate L7 Dimer

Intermediate L7 Dimer was prepared in the same manner as used to synthesize Intermediate L4 Dimer of Synthesis Example 1, except for the following: Intermediate L7 was used instead of Intermediate L4. Synthesis of compound 7

0.6 g (46% yield) of compound 7 was prepared in the same manner as used for the synthesis of compound 4 of Synthesis Example 1, except for the following: intermediate L7 Dimer and 3,7-diethylnonane were used, respectively -4,6-dione replaces the intermediate L4 Dimer and 3,7-diethyl-3,7-dimethylnonane-4,6-dione. LC-MS m/z = 1135(M+H) ⁺

中間物 L9-3 的合成 Synthesis Example 5 ( Compound 9 )

Synthesis of intermediate L9-3

2.1 g (80% yield) of intermediate L9-3 was prepared in the same manner as used for the synthesis of intermediate L4-3 of Synthesis Example 1, except for the following: 3,5-difluorophenylboronic acid was used Instead of 3-fluorophenylboronic acid. LC-MS m/z = 268(M+H) ⁺ Synthesis of intermediate L9-2

2.2 g (99% yield) of Intermediate L9-2 was prepared in the same manner as used for the synthesis of Intermediate L4-2 of Synthesis Example 1, except for the following: Intermediate L9-3 was used instead of Intermediate L4 -3. LC-MS m/z = 282(M+H) ⁺ Synthesis of intermediate L9-1

0.8 g (40% yield) of Intermediate L9-1 was prepared in the same manner as used for the synthesis of Intermediate L4-1 of Synthesis Example 1, except for the following: Intermediate L9-2 was used instead of Intermediate L4 -2. LC-MS m/z = 250(M+H) ⁺ Synthesis of intermediate L9

0.9 g of Intermediate L9 (87% yield) was prepared in the same manner as used for the synthesis of Intermediate L4 of Synthesis Example 1, except for the following: Intermediate L9-1 was used instead of Intermediate L4-1. LC-MS m/z = 320(M+H) ⁺ Synthesis of intermediate L9 Dimer

The intermediate L9 Dimer was prepared in the same manner as the intermediate L4 Dimer used to synthesize Synthesis Example 1, except that the intermediate L9 was used instead of the intermediate L4. Synthesis of compound 9

0.7 g (48% yield) of compound 9 was prepared in the same manner as used for the synthesis of compound 4 of Synthesis Example 1, except for the following: intermediate L9 Dimer and 3,3,7,7-tetra Methylnonane-4,6-dione replaces the intermediate L4 Dimer and 3,7-diethyl-3,7-dimethylnonane-4,6-dione. LC-MS m/z = 1043(M+H) ⁺

中間物 L16-3 的合成 Synthesis Example 6 ( Compound 16 )

Synthesis of intermediate L16-3

2.5 g (72% yield) of intermediate L16-3 was prepared in the same manner as used for the synthesis of intermediate L4-3 of Synthesis Example 1, except for the following: 2,5-difluorophenylboronic acid was used Instead of 3-fluorophenylboronic acid. LC-MS m/z = 268(M+H) ⁺ Synthesis of intermediate L16-2

2.6 g (98% yield) of Intermediate L16-2 was prepared in the same manner as used for the synthesis of Intermediate L4-2 of Synthesis Example 1, except for the following: Intermediate L16-3 was used instead of Intermediate L4 -3. LC-MS m/z = 282(M+H) ⁺ Synthesis of intermediate L16-1

0.9 g (38% yield) of Intermediate L16-1 was prepared in the same manner as used for the synthesis of Intermediate L4-1 of Synthesis Example 1, except for the following: Intermediate L16-2 was used instead of Intermediate L4- 2. LC-MS m/z = 250(M+H) ⁺ Synthesis of intermediate L16

0.8 g of Intermediate L16 (75% yield) was prepared in the same manner as used for the synthesis of Intermediate L4 of Synthesis Example 1, except for the following: Intermediate L16-1 was used instead of Intermediate L4-1. LC-MS m/z = 320(M+H) ⁺ Synthesis of intermediate L16 Dimer

The intermediate L16 Dimer was prepared in the same manner as the intermediate L4 Dimer used to synthesize Synthesis Example 1, except that the intermediate L16 was used instead of the intermediate L4. Synthesis of compound 16

0.6 g (40% yield) of compound 16 was prepared in the same manner as used for the synthesis of compound 4 of Synthesis Example 1, except that the intermediate L16 Dimer was used instead of the intermediate L4 Dimer. LC-MS m/z = 1071(M+H) ⁺

中間物 L18-2 的合成 Synthesis Example 7 (Compound 18 )

Synthesis of intermediate L18-2

2.6 g (80% yield) of Intermediate L18-2 was prepared in the same manner as used for the synthesis of Intermediate L1-2 of Synthesis Example 2, except for the following: 2-fluoro-6-(4, 4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trimethylsilyl)benzaldehyde instead of (3-fluoro-2-methyl Aminophenyl)boronic acid. LC-MS m/z = 322(M+H) ⁺ Synthesis of intermediate L18-1

0.7 g (30% yield) of Intermediate L18-1 was prepared in the same manner as used for the synthesis of Intermediate L1-1 of Synthesis Example 2, except for the following: Intermediate L18-2 was used instead of Intermediate L1 -2. LC-MS m/z = 304(M+H) ⁺ synthesis of intermediate L18

0.6 g (73% yield) of Intermediate L18 was prepared in the same manner as used for the synthesis of Intermediate L1 of Synthesis Example 2, except for the following: Intermediate L18-1 was used instead of Intermediate L1-1. LC-MS m/z = 374(M+H) ⁺ Synthesis of intermediate L18 Dimer

The intermediate L18 Dimer was prepared in the same manner as the intermediate L1 Dimer used to synthesize Synthesis Example 2, except that the intermediate L18 was used instead of the intermediate L1. Synthesis of compound 18

0.4 g (40% yield) of Compound 18 was prepared in the same manner as used for the synthesis of Compound 1 of Synthesis Example 2, except for the following: Intermediate L18 Dimer was used instead of Intermediate L1 Dimer. LC-MS m/z = 1180(M+H) ⁺

中間物 L23 的合成 Synthesis Example 8 (Compound 23 )

Synthesis of intermediate L23

Dissolve 1.2 g (3.7 mmol) of intermediate L9 in 60 ml of anhydrous tetrahydrofuran (THF), and then slowly add 2.4 ml (3.7 mmol) of 1.6 M BuLi in hexane to it at a temperature of -78°C . After about one hour, 0.7 ml (5.6 mmol) trimethylchlorogermane was slowly added dropwise thereto and stirred at room temperature for 18 hours. Once the reaction was completed, 50 ml of ethyl acetate and saturated sodium thiosulfate aqueous solution were added thereto to extract the organic layer, and then the organic layer was dried by using magnesium sulfate and distilled under reduced pressure. The crude product was purified by liquid chromatography to obtain 1.2 g (76% yield) of intermediate L23. LC-MS m/z = 438(M+H) ⁺ Synthesis of intermediate L23 Dimer

Intermediate L23 Dimer was prepared in the same manner as the intermediate L6 Dimer used to synthesize Synthesis Example 3, except for the following: Intermediate L23 was used instead of Intermediate L6. Synthesis of compound 23

0.8 g (45% yield) of compound 23 was prepared in the same manner as used for the synthesis of compound 6 of Synthesis Example 3, except that the intermediate L23 Dimer was used instead of the intermediate L6 Dimer. LC-MS m/z = 1279(M+H) ⁺

中間物 L28-6 的合成 Synthesis Example 9 (Compound 28 )

Synthesis of intermediate L28-6

6.2 g (71% yield) of intermediate L28-6 was prepared in the same manner as used for the synthesis of intermediate L4-3 of Synthesis Example 1, except that (3-bromo-5-(三Fluoromethyl)phenyl)boronic acid replaces 3-fluorophenylboronic acid. LC-MS m/z = 364(M+H) ⁺ Synthesis of intermediate L28-5

6.5 g (98% yield) of Intermediate L28-5 was prepared in the same manner as used for the synthesis of Intermediate L4-2 of Synthesis Example 1, except for the following: Intermediate L28-6 was used instead of Intermediate L4 -3. LC-MS m/z = 392(M+H) ⁺ Synthesis of intermediate L28-4

2.1 g (35% yield) of Intermediate L28-4 was prepared in the same manner as used for the synthesis of Intermediate L4-1 of Synthesis Example 1, except for the following: Intermediate L28-5 was used instead of Intermediate L4 -2. LC-MS m/z = 360(M+H) ⁺ Synthesis of intermediate L28-3

Mix 2.1 g (5.9 mmol) of the intermediate L28-4 with 120 ml of acetonitrile, and then add 1.1 ml (8.9 mmol) of trimethylchlorosilane and 1.3 g (8.9 mmol) of NaI to it, and then at a temperature of 90°C Heat for 36 hours while refluxing. Once the reaction was completed, 60 ml of ethyl acetate and saturated sodium thiosulfate aqueous solution were added thereto to extract the organic layer, and then the organic layer was dried by using magnesium sulfate and distilled under reduced pressure. The crude product was purified by liquid chromatography to obtain 2.3 g (87% yield) of intermediate L28-3. LC-MS m/z = 452(M+H) ⁺ Synthesis of intermediate L28-2

1.8 g (80% yield) of Intermediate L28-2 was prepared in the same manner as used for the synthesis of Intermediate L4 of Synthesis Example 1, except for the following: Intermediate L28-3 was used instead of Intermediate L4-1. LC-MS m/z = 430(M+H) ⁺ Synthesis of intermediate L28-1

1.8 g (4.2 mmol) of intermediate L28-2 was mixed with 60 ml of tetrahydrofuran (THF) and 15 ml of water, and then 0.9 g (5.0 mmol) of 4,4,5,5-tetramethyl-2- (Pro-1-en-2-yl)-1,3,2-dioxolane, 0.1 g (0.4 mmol) Pd(OAc) ₂ , 0.3 g (0.8 mmol) Sphos, and 1.5 g (10.5 mmol) K ₂ CO ₃ and heating while refluxing at a temperature of 80° C. for 18 hours. When the reaction was completed, the organic layer obtained by subjecting the reaction mixture to an extraction process by using 50 ml of ethyl acetate was dried by using magnesium sulfate, distilled under reduced pressure, and purified by liquid chromatography to obtain 1.2 g (75 % Yield) of the intermediate L28-1. LC-MS m/z = 392(M+H) ⁺ Synthesis of intermediate L28

1.2 g (3.1 mmol) of intermediate L28-1 was mixed with 60 ml of ethanol, and then 0.1 g (10% by weight) of Pd/C was added thereto, and hydrogen was injected into it, followed by mixing at room temperature 18 hour. When the reaction was completed, the reaction mixture was allowed to pass through a pad of Celite, and then concentrated under reduced pressure, and then purified by liquid chromatography to obtain 1.1 g (90% yield) of intermediate L28. LC-MS m/z = 394(M+H) ⁺ Synthesis of intermediate L28 Dimer

The intermediate L28 Dimer was prepared in the same manner as the intermediate L4 Dimer used to synthesize Synthesis Example 1, except that the intermediate L28 was used instead of the intermediate L4. Synthesis of compound 28

0.6 g (38% yield) of compound 28 was prepared in the same manner as used for the synthesis of compound 4 of Synthesis Example 1, except that the intermediate L28 Dimer was used instead of the intermediate L4 Dimer. LC-MS m/z = 1219(M+H) ⁺

中間物 L20-3 的合成 Synthesis Example 10 ( Compound 20 )

Synthesis of intermediate L20-3

1.8 g (80% yield) of Intermediate L20-3 was prepared in the same manner as used for the synthesis of Intermediate L4-3 of Synthesis Example 1, except for the following: (3,5-Difluoro-4 -Methylphenyl)boronic acid replaces 3-fluorophenylboronic acid. LC-MS m/z = 268(M+H) ⁺ Synthesis of intermediate L20-2

1.9 g (97% yield) of Intermediate L20-2 was prepared in the same manner as used for the synthesis of Intermediate L4-2 of Synthesis Example 1, except for the following: Intermediate L20-3 was used instead of Intermediate L4 -3. LC-MS m/z = 296(M+H) ⁺ Synthesis of intermediate L20-1

0.8 g (47% yield) of Intermediate L20-1 was prepared in the same manner as used for the synthesis of Intermediate L4-1 of Synthesis Example 1, except for the following: Intermediate L20-2 was used instead of Intermediate L4 -2. LC-MS m/z = 264(M+H) ⁺ synthesis of intermediate L20

0.8 g (84% yield) of Intermediate L20 was prepared in the same manner as used for the synthesis of Intermediate L4 of Synthesis Example 1, except for the following: Intermediate L20-1 was used instead of Intermediate L4-1. LC-MS m/z = 333(M+H) ⁺ Synthesis of intermediate L20 Dimer

Intermediate L20 Dimer was prepared in the same manner as the intermediate L4 Dimer used to synthesize Synthesis Example 1, except for the following: Intermediate L20 was used instead of Intermediate L4. Synthesis of compound 20

0.5 g (40% yield) of compound 20 was prepared in the same manner as used for the synthesis of compound 4 of Synthesis Example 1, except that the intermediate L20 Dimer was used instead of the intermediate L4 Dimer. LC-MS m/z = 1099(M+H) ⁺

中間物 L34 的合成 Synthesis Example 11 ( Compound 34 )

Synthesis of intermediate L34

1.0 g (78% yield) of Intermediate L34 was prepared in the same manner as used for the synthesis of Intermediate L1 of Synthesis Example 2, except for the following: (3,5-bis(methyl-d3)benzene was used) Yl)boronic acid instead of 3,5-dimethylphenylboronic acid. LC-MS m/z = 308(M+H) ⁺ Synthesis of intermediate L34 Dimer

The intermediate L34 Dimer was prepared in the same manner as the intermediate L4 Dimer used in the synthesis of Synthesis Example 1, except that the intermediate L34 was used instead of the intermediate L4. Synthesis of compound 34

0.8 g (52% yield) of compound 34 was prepared in the same manner as used for the synthesis of compound 4 of Synthesis Example 1, except that the intermediate L34 Dimer was used instead of the intermediate L4 Dimer. LC-MS m / z = 1045 (M + H) + Evaluation Example 1: Evaluation of photoluminescence quantum yield (PLQY) of

Compound H52 and Compound 4 were co-deposited under a vacuum pressure of 10 ^-7 Torr and in a weight ratio of 98:2 to produce a 40 nm thick film.

Evaluate in the film by using a Hamamatsu Photonics absolute PL quantum yield measurement system (Hamamatsu Photonics, Ltd., Shizuoka, Japan) equipped with a xenon light source, a monochromator, a photon multichannel analyzer, and an integrating sphere and using PLQY measurement software PLQY of compound 4. The results are shown in Table 1.

The PLQY of each of compounds 4, 1, 6, 7, 9, 16, 18, 23, 28, 34, 20, A1, B1, and C1 were measured, and the results are shown in Table 1. [Table 1] Compound number PLQY in the film (%) 4 99 1 99 6 99 7 98 9 99 16 97 18 97 twenty three 98 28 99 34 99 20 99 A1 90 B1 88 C1 90

From Table 1, it was confirmed that compounds 4, 1, 6, 7, 9, 16, 18, 23, 28, 34, and 20 showed better PLQY characteristics than compounds A1, B1, and C1. Evaluation Example 2: Evaluation of rate of horizontal orientation (optical orientation ratio)

In a vacuum deposition apparatus having a vacuum pressure of 10 ^-7 Torr, Compound H52 and Compound 4 were co-deposited on a fused silica layer (thickness of 1 mm) at a weight ratio of 98:2 to form a 40 nm thick film. Then, the film was sealed with glass and glue in a nitrogen environment.

At the same time, an angle-dependent PL measuring device having the structure shown in FIG. 3 of Korean Application No. 2013-0150834 is prepared. The specific specifications are as follows: -Excitation light wavelength: 325 nm -Excitation light source: He-Cd laser, Melles Griot, Inc. -Excitation light irradiation component: optical fiber, 1 mm diameter, Thorlabs, Inc. -Semi-cylindrical prism: fused silica, 100 mm diameter and 30 mm length, -Emission light detection component: photomultiplier tube, Acton, Inc. -Polarizer installed on the emitted light detection component: linear polarizer, Thorlabs, Inc. -Recording equipment: SpectraSense, Acton, Inc. -Incident angle of excitation light: θP = 45°, θH = 0° -The distance from the sample to the emission light detection part (or the radius of the travel path of the emission light detection part): 900 mm Then, the film was fixed on the semi-cylindrical lens and irradiated with a 325 nm laser to emit light. The emitted light is guided through a polarizing film and the p-polarized photoluminescence intensity is measured for light at the maximum wavelength of the spectrum from 90 degrees to 0 degrees by using a charge coupled device (CCD) as follows: The semi-cylindrical lens rotates 1 degree at a time with respect to the axis of the lens.

Calculate the p-polarized photoluminescence intensity (first p-polarized photoluminescence intensity) displayed when each compound has a vertical orientation and the p-polarized photoluminescence intensity displayed when each compound has a horizontal orientation from 0 degrees to 90 degrees Each of the intensity (second p-polarized photoluminescence intensity). Such a weighted value was determined to measure the horizontal orientation ratio of the compound shown in Table 2: the p-polarized photoluminescence obtained by multiplying each of the first and second p-polarized photoluminescence intensities by the weighted value The luminous intensity matches the measured p-polarized photoluminescence intensity. The results are shown in Table 2. In this case, the angle-dependent photoluminescence spectrum was analyzed using a classic dipole mode in which emission from excitons were regarded as dissipation energy consumed from an oscillating dipole to evaluate the horizontal orientation rate with respect to compound 4.

The horizontal orientation rate of each of compounds 4, 1, 6, 7, 9, 16, 18, 23, 28, 34, 20, A1, B1, and C1 was measured, and the results are shown in Table 2. [Table 2] Co-deposition materials Horizontal orientation rate (optical orientation rate) (%) H52 compound 4 (2% by weight) 91 H52 compound 1 (2% by weight) 91 H52 compound 6 (2% by weight) 91 H52 compound 7 (2% by weight) 93 H52 compound 9 (2% by weight) 92 H52 compound 16 (2% by weight) 91 H52 Compound 18 (2% by weight) 93 H52 Compound 23 (2% by weight) 94 H52 compound 28 (2% by weight) 93 H52 compound 34 (2% by weight) 91 H52 compound 20 (2% by weight) 92 H52 compound A1 (2% by weight) 83 H52 compound B1 (2% by weight) 82 H52 compound C1 (2% by weight) 88

From Table 2, it was confirmed that compounds 4, 1, 6, 7, 9, 16, 18, 23, 28, 34, and 20 showed better horizontal orientation rate characteristics than compounds A1, B1, and C1. Example 1

A glass substrate with an ITO pattern with a thickness of 1500Å as an anode was cut into a size of 50 mm × 50 mm × 0.5 mm, cleaned with isopropanol and pure water ultrasonic waves for 5 minutes each, and then irradiated with ultraviolet light for 30 minutes and Cleaning is done by exposure to ozone. Then, the resulting substrate was mounted on a vacuum deposition apparatus.

HT3 and F6-TCNNQ were vacuum co-deposited on the ITO anode at a weight ratio of 98:2 to form a hole injection layer with a thickness of 100 Å, and HT3 was vacuum deposited on the hole injection layer to form a hole injection layer with a thickness of 1350 Å. Then, HT21 was vacuum deposited on the hole transport layer to form an electron blocking layer with a thickness of 300 Å.

Then, H52 (host) and compound 4 (dopant) were co-deposited on the electron blocking layer in a weight ratio of 98:2 to form an emission layer having a thickness of 400 Å.

實施例 2 至 11 和比較例 A1 至 C1 Then, ET3 and ET-D1 were co-deposited on the emission layer at a volume ratio of 50:50 to form an electron transport layer having a thickness of 350 Å, and ET-D1 was vacuum-deposited on the electron transport layer to form An electron injection layer having a thickness of 10Å, and Al was vacuum deposited on the electron injection layer to form a cathode having a thickness of 1000Å, thereby completing an ITO (1500Å) / HT3+F6-TCNNQ (2% by weight) ( 100Å) / HT3 (1350Å) / HT21 (300Å) / H52 + compound 4 (2wt%) (400Å) / ET3+ET-D1 (50%) (350Å) / ET-D1 (10Å) / Al(1000Å) Structure of organic light-emitting devices.

Examples 2 to 11 and Comparative Examples A1 to C1

An organic light-emitting device was manufactured in the same manner as in Example 1, except for the following: when forming an emission layer, for use as a dopant, the corresponding compound shown in Table 3 was used instead of Compound 4. Evaluation Example 3 : Evaluation of characteristics of organic light-emitting devices

Evaluation of the driving voltage, current density, maximum external quantum efficiency (Max EQE), FWHM of the EL spectrum, and maximum emission wavelength (peak emission wavelength) (λ) of the organic light-emitting devices manufactured according to Examples 1 to 11 and Comparative Examples A1 to C1, respectively _Maximum ) and life (LT ₉₇ ). The results are shown in Tables 3 and 4. The evaluation was performed using a current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1,000A), and for each organic light-emitting device, the elapsed time was measured until the luminance was reduced to 97% of the initial luminance at 100% The lifetime (LT ₉₇ ) (under 3500 nits) was evaluated by the amount of, and it was expressed as a relative value (%). [table 3] Dopant compound number in the emission layer Drive voltage (V) Current density (mA/cm ² ) Max EQE (%) FWHM (nm) Example 1 4 4.2 10 29 50 Example 2 1 4.2 10 29 50 Example 3 6 4.0 10 28 52 Example 4 7 4.0 10 30 52 Example 5 9 3.8 10 31 53 Example 6 16 4.1 10 30 52 Example 7 18 4.0 10 32 51 Example 8 twenty three 3.9 10 31 50 Example 9 28 4.1 10 30 54 Example 10 34 4.2 10 29 49 Example 11 20 3.9 10 31 50 Comparative example A1 A1 4.5 10 25 76 Comparative example B1 B1 4.7 10 twenty two 78 Comparative example C1 C1 4.4 10 twenty four 65 [Table 4] Dopant compound number in the emission layer λ _max (nm) Life (LT ₉₇ ) (relative value, %) Example 1 4 622 200 Example 2 1 622 185 Example 3 6 625 160 Example 4 7 623 180 Example 5 9 629 230 Example 6 16 622 150 Example 7 18 624 130 Example 8 twenty three 627 140 Example 9 28 626 170 Example 10 34 622 300 Example 11 20 626 190 Comparative example A1 A1 614 90 Comparative example B1 B1 605 95 Comparative example C1 C1 631 70

Referring to Tables 3 and 4, the FWHM of light emitted from the organic light emitting devices of Examples 1 to 11 is significantly smaller than the FWHM of light emitted from the organic light emitting devices of Comparative Examples A1 to C1. Therefore, it was confirmed that the organic light-emitting devices of Examples 1 to 11 had a higher color purity level than the organic light-emitting devices of Comparative Examples A1 to C1. It was confirmed that the organic light-emitting devices of Examples 1 to 11 had improved characteristics in terms of driving voltage, external quantum efficiency, and lifetime compared with the organic light-emitting devices of Comparative Examples A1 to C1.

The organometallic compound according to the embodiment of the present disclosure has excellent characteristics in terms of quantum luminous efficiency and horizontal orientation rate. Therefore, the emission peak of the electroluminescence spectrum of the organic light emitting device including the organometallic compound has a relatively narrow FWHM, and the organic light emitting device including the organometallic compound may have excellent external quantum efficiency and lifetime characteristics.

It should be understood that the embodiments described herein should only be considered in a descriptive sense and not for the purpose of limitation. Descriptions of features or aspects in each embodiment should typically be considered as available for other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, those skilled in the art will understand that, without departing from the spirit and scope as defined by the scope of the appended application, modifications in form and detail can be made therein Many changes.

10: Organic light-emitting devices 11: First electrode 15: Organic layer 19: second electrode

These and/or other aspects will become clearer and easier to understand from the following description of the embodiment considered in conjunction with FIG. 1, FIG. 1 is a schematic cross-sectional view of an organic light emitting device according to an embodiment.

10: Organic light-emitting devices

11: First electrode

15: Organic layer

19: second electrode

Claims (20)

The organometallic compound is represented by Formula 1: [Formula 1]

Wherein, in formula 1, Y ₂ is C, ring A ₂ is a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group, R ₁ -R ₈ , R ₁₃ -R ₁₇ and R ₂₀ Each independently is hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof , Sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C ₁ -C ₆₀ alkyl, substituted or unsubstituted C ₂ -C ₆₀ alkenyl, substituted or unsubstituted Substituted C ₂ -C ₆₀ alkynyl, substituted or unsubstituted C ₁ -C ₆₀ alkoxy, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenyl, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C _1- C ₆₀ heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q ₁ )( Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -Ge(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ), -P(=O )(Q ₈ )(Q ₉ ) or -P(Q ₈ )(Q ₉ ), provided that i) at least one of R ₁ -R ₈ includes at least one fluorine group (-F); and ii) R ₂₀ Neither the fluorine group (-F) nor the cyano group is included, d2 is an integer from 0 to 10, and when d2 is 2 or greater, two or more R ₂₀ are the same or different from each other, R ₁₈ and R _{19 is} each independently a substituted or unsubstituted C ₂ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group , Substituted or unsubstituted C ₁ -C ₆₀ alkoxy, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl, Substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenyl, substituted or unsubstituted C ₆ -C ₆₀ aryl, substituted Or unsubstituted C ₆ -C ₆₀ aryloxy, substituted or unsubstituted C ₆ -C ₆₀ arylthio, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl, substituted or unsubstituted A substituted monovalent non-aromatic fused polycyclic group or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, R ₁ -R ₈ Two or more are optionally linked to form unsubstituted or substituted with at least one R _1a is C ₅ -C ₃₀ carbocyclic group or unsubstituted or substituted by at least one R _1a is C ₁ -C ₃₀ A heterocyclic group, two or more of R ₂₀ in the number d2 are optionally connected to form a C ₅ -C ₃₀ carbocyclic group that is unsubstituted or substituted with at least one R _1a or is unsubstituted or R _1a is substituted with at least one C ₁ -C ₃₀ heterocyclic group, two R ₁₃ -R ₁₉ or more are optionally linked to form unsubstituted or substituted with at least one R _1a is C ₅ -C _{A 30-} carbocyclic group or a C ₁ -C ₃₀ heterocyclic group that is unsubstituted or substituted by at least one R _1a , R _1a is the same as described for R ₂ , substituted C ₁ -C ₆₀ alkyl, Substituted C ₂ -C ₆₀ alkyl, substituted C ₂ -C ₆₀ alkenyl, substituted C ₂ -C ₆₀ alkynyl, substituted C ₁ -C ₆₀ alkoxy, substituted C _3- C ₁₀ cycloalkyl, substituted C ₂ -C ₁₀ heterocycloalkyl, substituted C ₃ -C ₁₀ cycloalkenyl, substituted C ₂ -C ₁₀ heterocycloalkenyl, substituted C _6- C ₆₀ aryl, substituted C ₆ -C ₆₀ aryloxy, substituted C ₆ -C ₆₀ arylthio, substituted C ₁ -C ₆₀ heteroaryl, substituted monovalent non-aromatic fused The substituents of the polycyclic group and the substituted monovalent non-aromatic fused heteropolycyclic group are: deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid Group or its salt, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl or C ₁ -C ₆₀ alkoxy; C ₁ -C ₆₀ alkyl, C _2- C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl or C ₁ -C ₆₀ alkoxy are each substituted by deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H,- CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt , Phosphoric acid group or its salt, C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₂ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropoly Cyclic group, -N(Q ₁₁ )(Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -Ge(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -B(Q ₁₆ )(Q ₁₇ ), -P(=O)(Q ₁₈ )(Q ₁₉ ), -P(Q ₁₈ )(Q ₁₉ ) or any combination thereof; C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₂ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl, monovalent non-aromatic fused The polycyclic group or the monovalent non-aromatic fused heteropolycyclic group is each unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, Phosphoric acid group or its salt, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₁ -C ₆₀ alkoxy, C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₂ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ Arylthio, C ₁ -C ₆₀ heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q ₂₁ )(Q ₂₂ ), -Si( Q ₂₃ )(Q ₂₄ )(Q ₂₅ ), -Ge(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ), -B(Q ₂₆ )(Q ₂₇ ), -P(=O)(Q ₂₈ )(Q ₂₉ ), -P(Q ₂₈ )(Q ₂₉ ) or any combination thereof; -N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -Ge(Q ₃₃ ) (Q ₃₄ )(Q ₃₅ ), -B(Q ₃₆ )(Q ₃₇ ), -P(=O)(Q ₃₈ )(Q ₃₉ ) or -P(Q ₃₈ )(Q ₃₉ ); or any combination thereof , Where Q ₁ -Q ₉ , Q ₁₁ -Q ₁₉ , Q ₂₁ -Q ₂₉ and Q ₃₁ -Q ₃₉ are each independently hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; Nitro group; amidino group; hydrazine group; hydrazone group; carboxylic acid group or its salt; sulfonic acid group or its salt; phosphoric acid group or its salt; unsubstituted or deuterium, C ₁ -C ₆₀ alkyl , C ₆ -C ₆₀ aryl or C ₁ -C ₆₀ alkyl substituted by any combination thereof; C ₂ -C ₆₀ alkenyl; C ₂ -C ₆₀ alkynyl; C ₁ -C ₆₀ alkoxy; C ₃ -C ₁₀ cycloalkyl; C ₂ -C ₁₀ heterocycloalkyl; C ₃ -C ₁₀ cycloalkenyl; C ₂ -C ₁₀ heterocycloalkenyl; unsubstituted or deuterated or C ₁ -C ₆₀ alkyl, C ₆ -C ₆₀ aryl group, or any combination thereof C ₆ -C ₆₀ substituted aryl group; C ₆ -C ₆₀ aryloxy; C ₆ -C ₆₀ aryl group; C ₁ -C ₆₀ heteroaryl Group; a monovalent non-aromatic fused polycyclic group; or a monovalent non-aromatic fused heteropolycyclic group. The organometallic compound described in item 1 of the scope of patent application, wherein ring A ₂ is a phenyl group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, a pyrrole Group, cyclopentadiene group, silole group, benzothiophene group, benzofuran group, indole group, indene group, benzosilole group, dibenzothiophene group, A dibenzofuran group, a azole group, a fluorene group, or a dibenzosilole group. The organometallic compound as described in item 1 of the scope of patent application, wherein R ₁ -R ₈ , R ₁₃ -R ₁₇ and R ₂₀ are each independently hydrogen, deuterium, -F, substituted or unsubstituted C _1- C ₂₀ alkyl, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl, -Si(Q ₃ )(Q ₄ )(Q ₅ ) or -Ge(Q ₃ )(Q ₄ )(Q ₅ ). The organometallic compound as described in item 1 of the scope of patent application, wherein R ₁ -R ₈ and R ₁₃ -R ₁₇ are each independently: hydrogen, deuterium or -F; C ₁ -C ₂₀ alkyl, C ₃ -C ₁₀ cycloalkyl or C ₂ -C ₁₀ heterocycloalkyl, each unsubstituted or substituted with deuterium, -F, C ₁ -C ₂₀ alkyl, C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ Heterocycloalkyl or any combination thereof; or -Si(Q ₃ )(Q ₄ )(Q ₅ ) or -Ge(Q ₃ )(Q ₄ )(Q ₅ ), and R ₂₀ is hydrogen or deuterium; C ₁ -C ₂₀ alkyl, C ₃ -C ₁₀ cycloalkyl, or C ₂ -C ₁₀ heterocycloalkyl, each unsubstituted or substituted with: deuterium, C ₁ -C ₂₀ alkyl, C ₃ -C ₁₀ Cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl, or any combination thereof; or -Si(Q ₃ )(Q ₄ )(Q ₅ ) or -Ge(Q ₃ )(Q ₄ )(Q ₅ ). The organometallic compound described in item 1 of the scope of patent application, wherein at least one of R ₁ -R ₈ is each independently: a fluorine group (-F); or a fluorinated C ₁ -C ₂₀ alkyl group, fluorinated C ₃ -C ₁₀ cycloalkyl or fluorinated C ₂ -C ₁₀ heterocycloalkyl, each unsubstituted or substituted with deuterium, C ₁ -C ₂₀ alkyl, C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl or any combination thereof. The organometallic compound described in item 1 of the scope of patent application, wherein R ₁₈ and R ₁₉ are each independently a substituted or unsubstituted C ₂ -C ₆₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl or substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl. The organometallic compound described in item 1 of the scope of patent application, wherein R ₁₈ and R ₁₉ are each independently a C ₂ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group or a C ₂ -C ₁₀ heterocycloalkyl group , Each is unsubstituted or substituted with deuterium, -F, C ₁ -C ₂₀ alkyl, C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl, or any combination thereof. The organometallic compound as described in item 1 of the patent application, wherein at least one of R _{4 to} R ₈ includes at least one fluorine group (-F). The organometallic compound as described in item 1 of the patent application, wherein one or two of R ₁ -R ₈ each independently includes at least one fluorine group (-F), and at least one of R ₁ -R ₈ i) does not include the fluorine group (-F), and ii) is not hydrogen. The organometallic compound as described in item 1 of the scope of patent application, wherein the formula 1 is

The represented group is a group represented by one of formulas CY1 to CY88:

Wherein, in formulas CY1 to CY88, T ₄ -T ₈ are each independently: fluorine group (-F); or fluorinated C ₁ -C ₂₀ alkyl, fluorinated C ₃ -C ₁₀ cycloalkyl or fluorine C ₂ -C ₁₀ heterocycloalkyl, each unsubstituted or substituted by deuterium, C ₁ -C ₂₀ alkyl, C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl, or Any combination, wherein R ₂ , R ₅ -R ₈ and R _1a are each the same as described in item 1 of the scope of the patent application, and R ₂ and R ₅ -R ₈ are not hydrogen, *'means the same as in formula 1. The binding site of Ir, and *" indicates the binding site with the adjacent atom in Formula 1. The organometallic compound as described in item 10 of the scope of patent application, wherein R ₂ and R ₅ -R ₈ in formulas CY1 to CY88 are each independently: deuterium; or C ₁ -C ₂₀ alkyl, C ₃ -C ₁₀ Cycloalkyl or C ₁ -C ₁₀ heterocycloalkyl, each unsubstituted or substituted with deuterium, C ₁ -C ₂₀ alkyl, C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkane基 or any combination thereof. The organometallic compound as described in item 1 of the scope of patent application, wherein the formula 1 is

The represented group is a group represented by one of formula A(1) to formula A(7):

Among them, in formula A(1) to formula A(7), Y ₂ is C, X ₂ is O, S, N(R ₂₅ ), C(R ₂₅ )(R ₂₆ ) or Si(R ₂₅ )( R ₂₆ ), R ₉ -R ₁₂ and R ₂₁ -R ₂₆ are each the same as described for R ₂₀ in the first item of the scope of patent application, *'represents the binding site with Ir in formula 1, and *" represents The binding site with the adjacent atom in Formula 1. The organometallic compound as described in item 12 of the scope of patent application, wherein R ₉ and R ₁₁ in formula A(1) are independently C ₁ -C ₂₀ alkyl, C ₃ -C ₁₀ cycloalkyl or C ₂ -C ₁₀ heterocycloalkyl, each unsubstituted or substituted with deuterium, C ₁ -C ₂₀ alkyl, C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl, or any combination thereof. The organometallic compound described in item 1 of the scope of patent application, wherein R ₁₄ and R _{16 are} not hydrogen. The organometallic compound as described in item 1 of the patent application, wherein the number of carbons in the group represented by *-C(R ₁₃ )(R ₁₄ )(R ₁₉ ) in Formula 1 is 5 or more, And the number of carbons in the group represented by *-C(R ₁₆ )(R ₁₇ )(R ₁₈ ) in Formula 1 is 5 or more. The organometallic compound according to item 1 of the scope of patent application, wherein the organometallic compound is one of the following compounds 1 to 38:

. Organic light-emitting devices, including: First electrode Second electrode; and An organic layer disposed between the first electrode and the second electrode and including an emission layer, The organic layer includes at least one organometallic compound as described in item 1 of the scope of the patent application. The organic light-emitting device as described in item 17 of the scope of patent application, wherein The first electrode is an anode, The second electrode is a cathode, The organic layer further includes a hole transport area between the first electrode and the emission layer and an electron transport area between the emission layer and the second electrode, The hole transport area includes a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer or any combination thereof, and The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer or any combination thereof. The organic light-emitting device as described in item 17 of the scope of patent application, wherein The organometallic compound is included in the emission layer. The organic light-emitting device as described in item 19 of the scope of patent application, wherein The emission layer emits red light.

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