CN114213397A - 1, 3-diazafluorenone derivatives and electronic devices - Google Patents

1, 3-diazafluorenone derivatives and electronic devices Download PDF

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CN114213397A
CN114213397A CN202111513809.0A CN202111513809A CN114213397A CN 114213397 A CN114213397 A CN 114213397A CN 202111513809 A CN202111513809 A CN 202111513809A CN 114213397 A CN114213397 A CN 114213397A
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diazafluorenone
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carbon atoms
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朱向东
张业欣
袁晓冬
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Weisipu New Material Suzhou Co ltd
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Abstract

The present invention relates to 1, 3-diazafluorenone derivatives and electronic devices. The 1, 3-diazafluorenone derivative has an excellent thermal stability by introducing a 1, 3-diazafluorenone structure, and is used for preparing an organic electroluminescent device. In addition, the 1, 3-diazafluorenone derivative of the present invention can be used as a material constituting a light-emitting layer, a hole blocking layer or an electron transport layer, and can reduce driving voltage, improve efficiency, luminance, lifetime, and the like.

Description

1, 3-diazafluorenone derivatives and electronic devices
Technical Field
The invention belongs to the technical field of organic photoelectric materials, and relates to a 1, 3-diazafluorenone derivative and an electronic device containing the 1, 3-diazafluorenone derivative. More particularly, the present invention relates to a 1, 3-diazafluorenone derivative suitable for use in an electronic device, particularly an organic electroluminescent device cell, and an electronic device using the 1, 3-diazafluorenone derivative.
Background
Organic Light-emitting Devices (OLEDs) are spontaneous Light-emitting Devices that utilize the following principle: when an electric field is applied, the fluorescent substance emits light by recombination of holes injected from the positive electrode and electrons injected from the negative electrode. The self-luminous device has the characteristics of low voltage, high brightness, wide viewing angle, quick response, good temperature adaptability and the like, is ultrathin, can be manufactured on a flexible panel and has a series of advantages of full curing, simple composition and process and the like, and compared with a liquid crystal display, the organic electroluminescent device does not need a backlight source. The method is widely applied to the fields of mobile phones, tablet computers, televisions, lighting and the like.
Organic electroluminescent devices generally comprise an anode, a metal cathode and an organic layer sandwiched therebetween. The organic layer mainly comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer. In addition, a host-guest structure is often used for the light-emitting layer. That is, the light emitting material is doped in the host material at a certain concentration to avoid concentration quenching and triplet-triplet annihilation, improving the light emitting efficiency. Therefore, the host material is generally required to have a higher triplet energy level and, at the same time, a higher stability.
At present, research on organic electroluminescent materials has been widely conducted in academia and industry, and a large number of organic electroluminescent materials with excellent performance have been developed. In view of the above, the future direction of organic electroluminescent devices is to develop high efficiency, long lifetime, low cost white light devices and full color display devices, but the industrialization of the technology still faces many key problems. The glass transition temperature of the existing electron transport materials which are frequently used in the market is lower and is generally less than 85 ℃, the molecular structure or the crystalline state can be changed due to the generated Joule heat when devices run, so that the panel efficiency is lower and the thermal stability is poorer, the molecular structure is very regular in symmetry, and the materials are very easy to crystallize after a long time. Once the electron transport material is crystallized, the charge transition mechanism between molecules is different from the amorphous thin film mechanism in normal operation, resulting in the decrease of electron transport performance, the imbalance of electron and hole mobility of the whole device, the great decrease of exciton formation efficiency, and the concentration of exciton formation at the interface of the electron transport layer and the light emitting layer, resulting in the severe decrease of device efficiency and lifetime. Therefore, designing and searching a stable and efficient compound as a novel material of an organic electroluminescent device to overcome the defects of the organic electroluminescent device in the practical application process is a key point in the research work of the organic electroluminescent device material and the future research and development trend.
Disclosure of Invention
Problems to be solved by the invention
Currently, 1, 3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBi) and the like are commonly used as host materials in OLED devices. Although the device has good device efficiency, the glass transition temperature of the device is low, and the driving voltage is high, further limiting the industrial application of the device.
Means for solving the problems
A1, 3-diazafluorenone derivative represented by the following general formula (I):
Figure BDA0003403373310000031
wherein X is a single bond, CR2O, S or not forming a bond;
R1，R2，R3represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, iodineAtom, cyano group, NO2、N(R)2、OR、SR、C(＝O)R、P(＝O)R、Si(R)3A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 30 carbon atoms; wherein R represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; substituted or unsubstituted alkenyl having 2 to 20 carbon atoms; substituted or unsubstituted aromatic hydrocarbon groups having 6 to 30 carbon atoms;
when R is1，R2，R3In the case of an aromatic hydrocarbon group or an aromatic heterocyclic group, the adjacent benzene rings may be connected to each other through a condensed ring.
Further, the 1, 3-diazafluorenone derivative represented by the general formula (I) is selected from the following compounds:
Figure BDA0003403373310000032
Figure BDA0003403373310000041
further, the 1, 3-diazafluorenone derivative represented by the general formula (I) is selected from the following compounds:
Figure BDA0003403373310000042
further, the 1, 3-diazafluorenone derivative represented by the general formula (I) is selected from the following compounds:
Figure BDA0003403373310000043
further, the 1, 3-diazafluorenone derivative represented by the general formula (I) is selected from the following compounds:
Figure BDA0003403373310000044
further, the 1, 3-diazafluorenone derivative represented by the general formula (I) is selected from the following compounds:
Figure BDA0003403373310000051
an electronic device comprising a 1, 3-diazafluorenone derivative of the general formula (I) above.
Further, the electronic device is an organic electroluminescent device;
specifically, the organic electroluminescent device comprises a first electrode, a second electrode disposed opposite to the first electrode, and at least one organic layer sandwiched between the first electrode and the second electrode, the at least one organic layer comprising the above-mentioned 1, 3-diazafluorenone derivative.
Further optionally, the at least one organic layer is a light emitting layer, a hole blocking layer, or an electron transport layer.
According to the invention, the bipolar 1, 3-diazafluorenone compound has a special biphenyl structure, higher thermal stability, chemical stability and carrier transport property, more importantly, the compound has appropriate singlet state, triplet state and molecular orbital energy level, and the HOMO/LUMO energy level of the compound is easy to regulate and control through reasonable material design. Therefore, the organic electroluminescent material is introduced into molecules with electroluminescent characteristics, so that the stability and the luminous efficiency of a device are improved, and the driving voltage of the device is reduced.
ADVANTAGEOUS EFFECTS OF INVENTION
The 1, 3-diazafluorenone derivative has good film forming property and thermal stability by introducing a 1, 3-diazafluorenone rigid structure, can be used for preparing electronic devices such as organic electroluminescent devices, particularly used as a constituent material of a light emitting layer, a hole blocking layer or an electron transport layer in the organic electroluminescent devices, can show the advantages of high luminous efficiency, long service life and low driving voltage, and is obviously superior to the existing organic electroluminescent devices.
In addition, the preparation method of the 1, 3-diazafluorenone derivative is simple, raw materials are easy to obtain, and the industrial development requirement can be met.
The 1, 3-diazafluorenone derivative has good application effect in electronic devices such as organic electroluminescent devices and the like, and has wide industrialization prospect.
The 1, 3-diazafluorenone derivative has stronger electron withdrawing of a central nucleus, excellent hole blocking capacity and excellent electron transmission performance, and is stable in a thin film state. Therefore, the organic electroluminescent device having a hole blocking layer prepared using the 1, 3-diazafluorenone derivative of the present invention has high luminous efficiency, a reduced driving voltage, and improved current resistance, so that the maximum luminous brightness of the organic electroluminescent device is increased.
The 1, 3-diazafluorenone derivative can be used as a material for forming a light-emitting layer, a hole blocking layer or an electron transport layer of an organic electroluminescent device. With the organic electroluminescent device of the present invention, excitons generated in the light emitting layer can be confined, and the possibility of recombination of holes and electrons can be further increased to obtain high luminous efficiency. In addition, the driving voltage is so low that high durability can be achieved.
Drawings
Fig. 1 is an electroluminescence spectrum of an organic electroluminescence device 3 of an embodiment of the present invention.
Fig. 2 is a configuration diagram showing an organic electroluminescent device of an example and an organic electroluminescent device of a comparative example.
Description of the reference numerals
1-substrate, 2-anode, 3-hole injection layer, 4-hole transport layer, 5-electron barrier layer, 6-luminescent layer, 7-hole barrier layer, 8-electron transport layer, 9-electron injection layer and 10-cathode.
Detailed Description
Hereinafter, embodiments of the present invention will be described in detail. However, the present invention is not limited to the following embodiments.
Examples
The production of the compound represented by the above general formula (I) and the organic electroluminescent device comprising the same is specifically described in the following examples. However, the following examples are only for illustrating the present invention, and the scope of the present invention is not limited thereto.
Example 1: synthesis of Compounds 1-7
(Synthesis of intermediate M1)
The synthetic route for intermediate M1 is shown below:
Figure BDA0003403373310000071
2- (4-bromophenyl) -1, 3-diazafluorene (6.46g, 20mmol), chromium trioxide (2.5g, 25mmol) and 120mL of acetic acid were added in this order to a 250mL single-neck flask, and the reaction was stirred under reflux for 4 hours. After the reaction, the reaction mixture was cooled to room temperature. The reaction solution was poured into water and extracted with dichloromethane. The organic phase was washed with saturated sodium bicarbonate solution. The organic phase was dried and evaporated under reduced pressure and the crude product was further purified by column chromatography (petroleum ether: dichloromethane ═ 2: 1 (V/V)). The solvent was evaporated and dried to give 3.50g of a yellow solid with a yield of 52%. Ms (ei): m/z: 337.02[ M ]+]。Anal.calcd for C17H9BrN2O(％)：C 60.56，H2.69，N 8.31；found：C 60.53，H 2.73，N 8.30。
(Synthesis of Compounds 1 to 7)
The synthetic routes for compounds 1-7 are shown below:
Figure BDA0003403373310000081
under the protection of nitrogen, the materials are added into a 250mL Schlenk bottle in sequenceIntermediate M1(1.69g, 5mmol), 7H-benzofuran [2, 3-B]Carbazole (1.31g, 5.1mmol), palladium acetate (22.4mg, 0.1mmol), tri-tert-butylphosphine tetrafluoroborate (73mg, 0.25mmol), sodium tert-butoxide (1.0g, 10mmol) and 120mL of toluene were reacted under reflux for 12 hours. After the reaction was completed, the solvent was distilled off, the residue was dissolved in 200mL of dichloromethane, washed with water, the organic layer was separated, the aqueous layer was extracted twice with 15mL of dichloromethane, and the organic layers were combined. After evaporation of the solvent, the residue was isolated by column chromatography (petroleum ether: dichloromethane: 2: 1 (V/V)). The solvent was evaporated and dried to give 1.87g of an orange solid with a yield of 73%. Ms (ei): m/z: 513.23[ M ]+]。Anal.calcd for C35H19N3O2(％)：C 81.86，H 3.73，N 8.18；found：C 81.80，H 3.70，N 8.11。
Example 2: synthesis of Compound 2-2
The synthetic route of compound 2-2 is shown below:
Figure BDA0003403373310000082
under nitrogen protection, intermediate M1(1.69g, 5mmol), bis (4-biphenylyl) amine (1.64g, 5.1mmol), palladium acetate (22.4mg, 0.1mmol), tri-tert-butylphosphine tetrafluoroborate (73mg, 0.25mmol), sodium tert-butoxide (1.0g, 10mmol) and 120mL of toluene were added in this order to a 250mL Schlenk flask, and the reaction was stirred under reflux for 12 hours. After the reaction was completed, the solvent was distilled off, the residue was dissolved in 200mL of dichloromethane, washed with water, the organic layer was separated, the aqueous layer was extracted twice with 15mL of dichloromethane, and the organic layers were combined. After evaporation of the solvent, the residue was isolated by column chromatography (petroleum ether: dichloromethane: 2: 1 (V/V)). The solvent was evaporated and dried to give 2.25g of an orange-red solid with a yield of 78%. Ms (ei): m/z: 577.50[ M ]+]。Anal.calcd for C41H27N3O(％)：C 85.25，H 4.71，N 7.27；found：C 85.10，H 4.70，N 7.22。
Example 3: synthesis of Compound 3-1
The synthetic route of compound 3-1 is shown below:
Figure BDA0003403373310000091
under nitrogen protection, intermediate M1(1.69g, 5mmol), 9, 10-dihydro-9, 9-dimethylacridine (1.05g, 5.1mmol), palladium acetate (22.4mg, 0.1mmol), tri-tert-butylphosphine tetrafluoroborate (73mg, 0.25mmol), sodium tert-butoxide (1.0g, 10mmol) and 120mL of toluene were added in this order to a 250mL Schlenk flask, and the reaction was stirred under reflux for 12 hours. After the reaction was completed, the solvent was distilled off, the residue was dissolved in 200mL of dichloromethane, washed with water, the organic layer was separated, the aqueous layer was extracted twice with 15mL of dichloromethane, and the organic layers were combined. After evaporation of the solvent, the residue was isolated by column chromatography (petroleum ether: dichloromethane: 2: 1 (V/V)). The solvent was evaporated and dried to give 1.63g of an orange solid with a yield of 71%. Ms (ei): m/z: 465.58[ M ]+]。Anal.calcd for C32H23N3O(％)：C 82.56，H 4.98，N 9.03；found：C 82.50，H 4.14，N 9.48。
Example 4: synthesis of Compound 4-1
The synthetic route of compound 4-1 is shown below:
Figure BDA0003403373310000101
under nitrogen protection, intermediate M1(1.69g, 5mmol), phenoxazine (0.91g, 5.1mmol), palladium acetate (22.4mg, 0.1mmol), tri-tert-butylphosphine tetrafluoroborate (73mg, 0.25mmol), sodium tert-butoxide (1.0g, 10mmol) and 120mL of toluene were added in sequence to a 250mL Schlenk flask, and the reaction was stirred under reflux for 12 hours. After the reaction was completed, the solvent was distilled off, the residue was dissolved in 200mL of dichloromethane, washed with water, the organic layer was separated, the aqueous layer was extracted twice with 15mL of dichloromethane, and the organic layers were combined. After evaporation of the solvent, the residue was isolated by column chromatography (petroleum ether: dichloromethane: 2: 1 (V/V)). The solvent was evaporated and dried to give 1.01g of an orange yellow solid with a yield of 68%. Ms (ei): m/z: 439.58[ M ]+]。Anal.calcd for C29H17N3O2(％)：C 79.26，H 3.90，N 9.56；found：C 79.20，H 3.90，N 9.57。
Example 5: synthesis of Compound 5-1
The synthetic route of compound 5-1 is shown below:
Figure BDA0003403373310000102
under nitrogen protection, intermediate M1(1.69g, 5mmol), phenothiazine (1.01g, 5.1mmol), palladium acetate (22.4mg, 0.1mmol), tri-tert-butylphosphine tetrafluoroborate (73mg, 0.25mmol), sodium tert-butoxide (1.0g, 10mmol) and 120mL of toluene were added in this order to a 250mL Schlenk flask, and the reaction was stirred at reflux for 12 hours. After the reaction was completed, the solvent was distilled off, the residue was dissolved in 200mL of dichloromethane, washed with water, the organic layer was separated, the aqueous layer was extracted twice with 15mL of dichloromethane, and the organic layers were combined. After evaporation of the solvent, the residue was isolated by column chromatography (petroleum ether: dichloromethane: 2: 1 (V/V)). The solvent was evaporated and dried to give 1.71g of an orange solid with a yield of 75%. Ms (ei): m/z: 455.58[ M ]+]。Anal.calcd for C29H17N3OS(％)：C 76.46，H 3.76，N 9.22；found：C 76.40，H 3.70，N 9.21。
Example 6: preparation of organic electroluminescent device 1 (organic EL device 1)
A hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9 and a cathode 10 were sequentially formed on a transparent anode 2 previously formed on a glass substrate 1 to prepare an organic electroluminescent device as shown in fig. 2.
Specifically, a glass substrate on which an ITO film having a film thickness of 100nm was formed was subjected to ultrasonic treatment in a Decon 90 alkaline cleaning solution, rinsed in deionized water, washed three times in acetone and ethanol, respectively, baked in a clean environment to completely remove moisture, washed with ultraviolet light and ozone, and bombarded on the surface with a low-energy cation beam. Placing the glass substrate with ITO electrode into a vacuum chamber, and vacuumizing to 4 × 10-4-2×10-5Pa. Then, the ITO electrode was formed on the glass substrate at a deposition rate of 0.2nm/s2, 3, 6, 7, 10, 11-hexacyano-1, 4, 5, 8, 9, 12-hexaazatriphenylene (HAT-CN) was evaporated to form a layer having a thickness of 10nm as a hole injection layer. N, N '-diphenyl-N, N' - (1-naphthyl) -1, 1 '-biphenyl-4, 4' -diamine (NPB) was vapor-deposited on the hole injection layer at a vapor deposition rate of 0.2nm/s to form a layer having a film thickness of 40nm as a hole transport layer. 4, 4' -tris (N-carbazolyl) triphenylamine (TCTA) was vapor-deposited on the hole transport layer at a vapor deposition rate of 0.2nm/s to form a layer having a film thickness of 5nm as an Electron Blocking Layer (EBL). On the electron blocking layer, double-source co-evaporation was performed at a deposition rate of 0.2nm/s for the compound of example 1 (compound 1-7) as a host material and at a deposition rate of 0.016nm/s for RD1 as a dopant material to form a layer with a thickness of 20nm as a light-emitting layer, and the doping weight ratio of RD1 was 2 wt%. On the light-emitting layer, aluminum (III) bis (2-methyl-8-quinolinolato) -4-phenylphenolate (BALq) was vapor-deposited at a vapor deposition rate of 0.2nm/s to form a layer having a film thickness of 10nm as a Hole Blocking Layer (HBL). On the hole-blocking layer, BALq was deposited at a deposition rate of 0.2nm/s to form a layer having a thickness of 40nm as an electron-transporting layer (ETL). On the electron transport layer, 8-hydroxyquinoline-lithium (Liq) was vapor-deposited at a vapor deposition rate of 0.1nm/s to form a layer having a film thickness of 2nm as an electron injection layer. Finally, aluminum is vapor-deposited at a vapor deposition rate of 0.5nm/s or more to form a cathode having a film thickness of 100 nm.
Examples 7 to 10: preparation of organic EL devices 2 to 5
An organic EL device was produced under the same conditions as the organic EL device 1 except that the compounds in table 1 below were used instead of the compounds in each layer of example 6, respectively.
Comparative examples 1 to 2: preparation of organic EL device comparative examples 1 to 2
Comparative examples of organic EL devices were prepared under the same conditions as the organic EL device 1 except that the compounds in table 1 below were used instead of the compounds in each layer of example 6, respectively.
The examples and comparative examples relate to the following structures of compounds:
Figure BDA0003403373310000131
TABLE 1
Figure BDA0003403373310000132
Figure BDA0003403373310000141
Figure BDA0003403373310000151
The Tg characteristics of the organic EL devices 1 to 5 produced in examples 6 to 10 and the organic EL devices comparative examples 1 to 2 produced in comparative examples 1 to 2 were measured when a dc voltage was applied in the atmosphere at normal temperature. The measurement results are shown in table 2.
TABLE 2
Figure BDA0003403373310000152
Figure BDA0003403373310000161
As can be seen from Table 2, the 1, 3-diazafluorenone derivatives of the present invention achieve excellent Tg properties.
Compared with the materials commonly used in the prior art, the 1, 3-diazafluorenone derivative can effectively improve the glass transition temperature of the materials, reduce the working voltage and improve the stability of devices.
The 1, 3-diazafluorenone derivative of the present invention has excellent luminous efficiency and life characteristics, and a low driving voltage. Therefore, an organic electroluminescent device having an excellent lifetime can be prepared from the compound.
The invention is illustrated by the above examples of materials and their applications, but the invention is not limited to the above examples, i.e. it is not intended that the invention must be implemented in reliance on the above examples. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.

Claims (9)

1. A1, 3-diazafluorenone derivative represented by the following general formula (I):
Figure FDA0003403373300000011
wherein X is a single bond, CR2O, S or not forming a bond;
R1，R2，R3represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, NO2、N(R)2、OR、SR、C(＝O)R、P(＝O)R、Si(R)3A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 30 carbon atoms; wherein R represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; substituted or unsubstituted alkenyl having 2 to 20 carbon atoms; substituted or unsubstituted aromatic hydrocarbon groups having 6 to 30 carbon atoms;
when R is1，R2，R3In the case of an aromatic hydrocarbon group or an aromatic heterocyclic group, the adjacent benzene rings may be connected to each other through a condensed ring.
2. The 1, 3-diazafluorenone derivative according to claim 1, wherein the 1, 3-diazafluorenone derivative represented by the general formula (I) is selected from the group consisting of:
Figure FDA0003403373300000021
3. the 1, 3-diazafluorenone derivative according to claim 1, wherein the 1, 3-diazafluorenone derivative represented by the general formula (I) is selected from the group consisting of:
Figure FDA0003403373300000022
4. the 1, 3-diazafluorenone derivative according to claim 1, wherein the 1, 3-diazafluorenone derivative represented by the general formula (I) is selected from the group consisting of:
Figure FDA0003403373300000031
5. the 1, 3-diazafluorenone derivative according to claim 1, wherein the 1, 3-diazafluorenone derivative represented by the general formula (I) is selected from the group consisting of:
Figure FDA0003403373300000032
6. the 1, 3-diazafluorenone derivative according to claim 1, wherein the 1, 3-diazafluorenone derivative represented by the general formula (I) is selected from the group consisting of:
Figure FDA0003403373300000033
7. an electronic device comprising the 1, 3-diazafluorenone derivative according to any one of claims 1 to 6.
8. The electronic device of claim 7, wherein the electronic device is an organic electroluminescent device;
wherein the organic electroluminescent device comprises: a first electrode, a second electrode disposed opposite to the first electrode, and at least one organic layer interposed between the first electrode and the second electrode, the at least one organic layer comprising the 1, 3-diazafluorenone derivative according to any one of claims 1 to 6.
9. The electronic device of claim 8, wherein the at least one organic layer is a light emitting layer, a hole blocking layer, or an electron transport layer.
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CN101492447A (en) * 2009-02-23 2009-07-29 南京邮电大学 Carbazole organic semiconductor materials, methods for preparing and using same
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CN110746406A (en) * 2019-11-19 2020-02-04 苏州久显新材料有限公司 3, 4-diazafluorenone derivatives, method for synthesizing the same, and electronic device containing the 3, 4-diazafluorenone derivatives

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JPH08240921A (en) * 1995-03-02 1996-09-17 Mita Ind Co Ltd Electrophotographic photoreceptor
CN101492447A (en) * 2009-02-23 2009-07-29 南京邮电大学 Carbazole organic semiconductor materials, methods for preparing and using same
CN106414452A (en) * 2014-03-10 2017-02-15 三星Sdi株式会社 Condensed-ring compound and organic light-emitting element comprising same
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