CN110317186B - Novel organic compound and organic electroluminescent device comprising the same - Google Patents
Novel organic compound and organic electroluminescent device comprising the same Download PDFInfo
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- CN110317186B CN110317186B CN201910243556.6A CN201910243556A CN110317186B CN 110317186 B CN110317186 B CN 110317186B CN 201910243556 A CN201910243556 A CN 201910243556A CN 110317186 B CN110317186 B CN 110317186B
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- 150000002894 organic compounds Chemical class 0.000 title abstract description 11
- 239000012044 organic layer Substances 0.000 claims abstract description 26
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- 238000002347 injection Methods 0.000 claims description 48
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- 238000009877 rendering Methods 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 description 104
- 230000015572 biosynthetic process Effects 0.000 description 56
- 238000003786 synthesis reaction Methods 0.000 description 56
- 239000007858 starting material Substances 0.000 description 52
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- 125000003118 aryl group Chemical group 0.000 description 21
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 21
- 239000004065 semiconductor Substances 0.000 description 19
- 125000001424 substituent group Chemical group 0.000 description 19
- 239000010409 thin film Substances 0.000 description 18
- 125000000217 alkyl group Chemical group 0.000 description 13
- 239000011777 magnesium Substances 0.000 description 12
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- 125000001072 heteroaryl group Chemical group 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
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- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 3
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- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
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- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052705 radium Inorganic materials 0.000 description 1
- HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 101150072178 viaA gene Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Abstract
The present invention relates to novel organic compounds and organic electroluminescent devices comprising the same. More particularly, the present invention relates to deuterated organic compounds and organic electroluminescent devices comprising at least one organic layer made of deuterated organic compounds. Thus, the organic electroluminescent device exhibits a longer lifetime, a lower voltage realization, and improved luminous efficiency.
Description
Technical Field
The present disclosure relates to novel organic compounds and organic electroluminescent devices comprising the same. More particularly, the present disclosure relates to deuterated organic compounds and organic electroluminescent devices comprising at least one organic layer made from deuterated organic compounds.
Background
The organic electroluminescent device has a simpler structure than other flat panel display devices such as a Liquid Crystal Display (LCD), a Plasma Display Panel (PDP), and a Field Emission Display (FED). The organic electroluminescent device has various advantages in the manufacturing process, excellent brightness and viewing angle characteristics, and high response speed and low driving voltage. Accordingly, organic electroluminescent devices are actively being developed for flat panel displays such as wall-mounted televisions or as light sources (e.g., displays, lighting devices, and backlights of bulletin boards).
In general, in an organic electroluminescent device, holes injected from an anode and electrons injected from a cathode are recombined with each other to form excitons as electron-hole pairs when a voltage is applied thereto. Then, the energy of the exciton is transferred to the light emitting material to emit a light beam.
W.Tang reports a low voltage driven organic electroluminescent device comprising a stack of organic thin films formed between two opposing electrodes to improve the efficiency and stability of the organic electroluminescent device (C.W.Tang, S.A.Vanslyke, applied Physics Letters, vol. 51, page 913, 1987). Subsequently, research into organic materials for organic electroluminescent devices having organic thin film stacks has been actively conducted.
In general, an organic electroluminescent device has a structure such that: which comprises a cathode (electron injection electrode), an anode (hole injection electrode) and at least one organic layer between the two electrodes.
Most organic materials used in organic electroluminescent devices are pure organic materials or coordination complexes between organic materials and metals. Organic materials used for the organic electroluminescent device may be classified into hole injection materials, hole transport materials, light emitting materials, electron transport materials, and electron injection materials. In this regard, the hole injection material or the hole transport material may mainly employ an organic material that is easily oxidized and electrochemically stable in an oxidized state. The electron injecting material and the electron transporting material may mainly employ organic materials that are easily reduced and electrochemically stable in a reduced state.
The light-emitting layer material is preferably a material that is electrochemically stable in both the oxidized and reduced states. In addition, the light emitting layer material preferably employs a material having high light emitting efficiency, to which excitons are applied to emit a light beam. In a light-emitting layer made of a material having such characteristics, electrons and holes are recombined to generate an excited state. When the excited state returns to the ground state, light emission may occur. The type of compound of each organic layer ultimately affects the characteristics and implementation of the organic electroluminescent device.
Recently, organic electroluminescent devices require longer lifetime, lower voltage realization, and improved luminous efficiency. These requirements may lead to lower power consumption and improved endurance of the device.
For this reason, the present inventors have attempted to achieve low voltage implementation and improved lifetime using deuterated anthracene organic compounds containing polar molecules.
[ Prior Art literature ]
[ patent literature ]
Korean patent application laid-open No. 10-2013-0010633; korean patent No. 10-1368164
Disclosure of Invention
It is an object of the present disclosure to provide novel compounds that can be used as blue host materials for light emitting layers.
It is another object of the present disclosure to provide an organic electroluminescent device, wherein the device comprises a novel compound containing polar molecules to make the driving voltage lower, and wherein the device comprises a deuterated anthracene organic compound to achieve increased lifetime as well as excellent light emitting efficiency and External Quantum Efficiency (EQE) characteristics.
The objects of the present disclosure are not limited to the above objects. As not mentioned above, other objects and advantages of the present disclosure may be understood from the following description, and more clearly understood from the embodiments of the present disclosure. Furthermore, it is to be readily understood that the objects and advantages of the present disclosure may be realized by means of the elements and combinations thereof as disclosed in the appended claims.
In a first aspect of the present disclosure, there is provided a compound represented by the following chemical formula 1:
[ chemical formula 1]
Wherein Y represents a substituent represented by the following chemical formula 2:
[ chemical formula 2]
Wherein X is O or S,
n is an integer of 0 to 4,
m is an integer of 0 to 3,
wherein L is 1 And L 2 Identical or different from each other, and L 1 And L 2 Each independently represents one selected from: direct bond, substituted or unsubstitutedSubstituted arylene having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene having 6 to 30 ring constituent atoms, substituted or unsubstituted alkylene having 2 to 10 carbon atoms, substituted or unsubstituted cycloalkylene having 2 to 10 carbon atoms, substituted or unsubstituted alkenylene having 2 to 10 carbon atoms, substituted or unsubstituted cycloalkenylene having 2 to 10 carbon atoms, substituted or unsubstituted heteroalkylene having 2 to 10 carbon atoms, substituted or unsubstituted heterocycloalkylene having 2 to 10 carbon atoms, substituted or unsubstituted heterocycloalkenylene having 2 to 10 carbon atoms, and substituted or unsubstituted heterocycloalkenylene having 2 to 10 carbon atoms,
Wherein Ar is 1 Represents one selected from: a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted heteroalkenyl group having 1 to 20 carbon atoms,
wherein R is 1 To R 10 Identical or different from each other, and R 1 To R 10 Each independently represents one selected from: hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl having 2 to 24 carbon atoms, substituted or unsubstituted heteroalkyl having 2 to 30 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted hetero having 2 to 30 carbon atoms Aryl and substituted or unsubstituted heteroarylalkyl having 3 to 30 carbon atoms, wherein R 9 And R is 10 Each independently bonded to an adjacent group to form a ring,
wherein R is 1 To R 10 、L 1 And L 2 Ar, ar 1 Each independently substituted with at least one substituent selected from the group consisting of: hydrogen, deuterium, cyano, nitro, halogen, hydroxyl, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl having 2 to 24 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms, substituted or unsubstituted heteroarylalkyl having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 30 carbon atoms, substituted or unsubstituted alkylamino having 1 to 30 carbon atoms, substituted or unsubstituted arylamino having 6 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted arylamino having 1 to 30 carbon atoms, substituted or unsubstituted silyl having 1 to 30 carbon atoms,
Wherein L is 1 And L 2 Ar, ar 1 R is as follows 1 To R 10 At least one of the substituents of (a) comprises deuterium.
Furthermore, according to the present disclosure, R 1 To R 8 Preferably at least one of them comprises deuterium.
Furthermore, according to the present disclosure, L 1 Preferably comprising one selected from the group consisting of: a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstitutedSubstituted or unsubstituted heteroarylene having 6 to 30 ring members. L (L) 2 Preferably comprising a direct bond, or a substituted or unsubstituted phenylene group. More preferably L 1 Including a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
According to a preferred embodiment of the present disclosure, there is provided an organic electroluminescent device including a first electrode; a second electrode facing away from the first electrode; and at least one organic layer interposed between the first electrode and the second electrode, wherein the at least one organic layer comprises one or more compounds of formula 1.
Further, the organic layer according to the present disclosure defines one selected from: 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.
Further, the organic layer according to the present disclosure defines a light emitting layer, wherein the light emitting layer includes the compound of chemical formula 1 as a host material.
The organic electroluminescent device may include an anode, a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an emission layer (EML), an Electron Transport Layer (ETL), and an Electron Injection Layer (EIL) vertically stacked in this order. The device may further include an Electron Blocking Layer (EBL) and a Hole Blocking Layer (HBL) to improve light emitting efficiency of the light emitting layer, wherein the Electron Blocking Layer (EBL) and the Hole Blocking Layer (HBL) sandwich the light emitting layer (EML) therebetween.
In particular, the organic electroluminescent device may further comprise a further organic layer between the first electrode and the light emitting layer or between the light emitting layer and the second electrode, wherein the further organic layer defines at least one selected from the group consisting of: 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.
Furthermore, when the device is implemented as a tandem organic electroluminescent device, a single light emitting unit may be composed of a stack of at least two light emitting layers and a Charge Generating Layer (CGL) therebetween. The organic electroluminescent device may include two or more stacks on a substrate, wherein each stack includes a first electrode and a second electrode facing away from each other, and a vertical stack of light emitting layers disposed between the first electrode and the second electrode to emit a specific light beam. The light emitting layer coupled to the Charge Generation Layer (CGL) composed of the N-type charge generation layer and the P-type charge generation layer may exhibit blue, yellow, or green, or red.
In one embodiment of the present disclosure, an organic electroluminescent device is provided, which includes a first light emitting sub-stack for presenting a first color light, and a second light emitting sub-stack for presenting a second color light stacked on the first light emitting sub-stack, wherein at least one of the first light emitting sub-stack and the second light emitting sub-stack includes a host material, wherein the host material includes a compound represented by the following chemical formula 1:
[ chemical formula 1]
Wherein Y represents a substituent represented by the following chemical formula 2:
[ chemical formula 2]
Wherein X is O or S,
n is an integer of 0 to 4,
m is an integer of 0 to 3,
wherein L is 1 And L 2 Identical or different from each other, and L 1 And L 2 Each independently represents one selected from: a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 6 to 30 ring constituent atoms, a substituted or unsubstituted alkylene group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkylene group having 2 to 10 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkenylene group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkylene group having 2 to 10 carbon atoms Substituted heteroalkylene having 2 to 10 carbon atoms, substituted or unsubstituted heterocycloalkylene having 2 to 10 carbon atoms, substituted or unsubstituted heteroalkenylene having 2 to 10 carbon atoms, and substituted or unsubstituted heterocycloalkenylene having 2 to 10 carbon atoms,
wherein Ar is 1 Represents one selected from: a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted heteroalkenyl group having 1 to 20 carbon atoms,
wherein R is 1 To R 10 Identical or different from each other, and R 1 To R 10 Each independently represents one selected from: hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl having 2 to 24 carbon atoms, substituted or unsubstituted heteroalkyl having 2 to 30 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms, and substituted or unsubstituted heteroarylalkyl having 3 to 30 carbon atoms, wherein R 9 And R is 10 Each independently bonded to an adjacent group to form a ring,
wherein R is 1 To R 10 、L 1 And L 2 Ar, ar 1 Each independently substituted with at least one substituent selected from the group consisting of: hydrogen, deuterium, cyano, nitro, halogen radicals, hydroxy, viaA substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroarylalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted silyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 1 to 30 carbon atoms,
Wherein L is 1 And L 2 Ar, ar 1 R is as follows 1 To R 10 At least one of the substituents of (a) comprises deuterium.
Details of the compound represented by chemical formula 1 are as described above.
In one embodiment, the first light emitting sub-stack comprises a vertical stack of a first electrode, a first hole transport layer, a first light emitting layer, and a first electron transport layer in this order. The second light emitting sub-stack includes a vertical stack of a second hole transporting layer, a second light emitting layer, and a second electron transporting layer in this order. At least one of the first light emitting layer and the second light emitting layer may include a host material.
Fig. 1 is a schematic cross-sectional view of a tandem organic electroluminescent device having two light-emitting sub-stacks according to an exemplary first embodiment of the present disclosure. As shown in fig. 1, the organic electroluminescent device 100 according to the first embodiment of the present disclosure has a first electrode 110 and a second electrode 120 facing away from each other, and an organic light emitting stack 130 between the first electrode 110 and the second electrode 120. The organic light emitting stack 130 includes a first light emitting sub-stack (ST 1) 140 between the first electrode 110 and the second electrode 120 and including a first light emitting layer 144; a second light emitting sub-stack (ST 2) 150 between the first light emitting sub-stack 140 and the second electrode 120 and including a second light emitting layer 154; and a Charge Generation Layer (CGL) 160 disposed between the first light emitting sub-stack 140 and the second light emitting sub-stack 150.
The first electrode 110 serves as an anode for injecting holes. The first electrode 110 may be made of a conductive material having a high work function such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), and zinc oxide (ZnO). The second electrode 120 serves as a cathode for injecting electrons. The second electrode 120 may be made of a conductive material having a low work function such as aluminum (Al), magnesium (Mg), and aluminum-magnesium alloy (AlMg).
The first light emitting sub-stack 140 includes a vertical stack of a hole injection layer 141 between the first electrode 110 and the first light emitting layer 144, a first hole transport layer 142 between the hole injection layer 141 and the first light emitting layer 144, and a first electron transport layer 146 between the first light emitting layer 144 and the charge generating layer 160.
The hole injection layer 141 improves the characteristics of the interface between the inorganic first electrode 110 and the first hole transport layer 142, which is an organic layer. The hole injection layer 141 may include the compound represented by chemical formula 1 described above. In one example, the hole injection layer 141 may include at least one selected from the group consisting of: 4,4',4 "-tris (3-methylphenyl phenylamino) triphenylamine (MTDATA), copper phthalocyanine (CuPc), tris (4-carbazolyl-9-yl-phenyl) amine (TCTA), N' -diphenyl-N, N '-bis (1-naphthyl) -1,1' -biphenyl-4, 4" -diamine (NPB; NPD), 1,4,5,8,9,11-hexaazabenzophenanthrene Hexacarbonitrile (HATCN), 1,3, 5-tris [4- (diphenylamino) phenyl ] benzene (TDAPB), poly (3, 4-ethylenedioxythiophene) polystyrene sulfonate (PEDOT/PSS), 2,3,5, 6-tetrafluoro-7, 8-tetracyanoquinodimethane (F4-TCNQ) and/or N- (biphenyl-4-yl) -9, 9-dimethyl-N- (4- (9-phenyl-9H-carbazolyl-3-yl) phenyl) -9H-fluoren-2-amine.
In one example, the thickness of the hole injection layer 141 may be in the range of 1nm to 150 nm. When the thickness of the hole injection layer 141 is greater than or equal to 1nm, hole injection characteristics may be improved. When the thickness is 150nm or less, a problem of an increase in driving voltage due to an increase in the thickness of the hole injection layer 141 can be prevented. The hole injection layer 141 may be omitted according to the structure and characteristics of the organic electroluminescent device.
The first hole transport layer 142 is located between the hole injection layer 141 and the first light emitting layer 144. The first light emitting layer 144 is located between the first hole transporting layer 142 and the first electron transporting layer 146. The first electron transport layer 146 is located between the first light emitting layer 144 and the charge generating layer 160.
The second light emitting sub-stack 150 includes a vertical stack of a second hole transporting layer 152, a second light emitting layer 154, a second electron transporting layer 156, and an electron injecting layer 158 in this order. The second hole transport layer 152 is located between the charge generation layer 160 and the second light emitting layer 154. The second light emitting layer 154 is located between the second hole transporting layer 152 and the second electrode 120. In addition, the second electron transport layer 156 is located between the second light emitting layer 154 and the second electrode 120. The electron injection layer 158 is located between the second electron transport layer 156 and the second electrode 120.
Each of the first hole transport layer 142 and the second hole transport layer 152 may include the compound represented by chemical formula 1 as described above. In one example, the first hole transport layer 142 and the second hole transport layer 152 each may comprise at least one selected from the group consisting of: n, N '-diphenyl-N, N' -bis (3-methylphenyl) -1,1 '-biphenyl-4, 4' -diamine (TPD), NPD, MTDATA, 1, 3-bis (N-carbazolyl) benzene (mCP), cuPc, TCTA, tris (trifluorovinyl ether) -tris (4-carbazolyl-9-yl-phenyl) amine (TFV-TCTA), tris [4- (diethylamino) phenyl ] amine, N- (biphenyl-4-yl) -9, 9-dimethyl-N- (4- (9-phenyl-9H-carbazolyl-3-yl) phenyl) -9H-fluoren-2-amine, tri-p-tolylamine, N- [1,1 '-biphenyl ] -4-yl-9, 9-dimethyl-N- [4- (9-phenyl-9H-carbazolyl-3-yl) phenyl ] -amine), 4' -bis (N-carbazolyl) -1,1 '-biphenyl, CBP and/or 1, 1-bis (4- (N, N' -di (p-tolyl) amino) cyclohexane (tacp).
The thickness of each of the first hole transport layer 142 and the second hole transport layer 152 may be 1nm to 150nm. In this regard, when the thickness of each of the first hole transport layer 142 and the second hole transport layer 152 is 1nm or more, hole transport characteristics can be improved. When the thickness is 150nm or less, a problem of an increase in driving voltage due to an increase in the thickness of each of the first hole transport layer 142 and the second hole transport layer 152 can be prevented. The first hole transport layer 142 and the second hole transport layer 152 may be made of the same material or may be made of different materials.
In one exemplary embodiment, the first light emitting layer 144 and the second light emitting layer 154 may each include a host and a dopant doped into the host. The first light emitting layer 144 and the second light emitting layer 154 may exhibit different colors. The dopant material may be added at a content of about 1 to 30 wt% based on the weight of the host material.
In one example, the first light emitting layer 144 may exhibit blue (B), red (R), green (G), or yellow (Y). When the first light emitting layer 144 exhibits blue (B), the first light emitting layer 144 includes one of a blue light emitting material layer, or a deep blue light emitting material layer, or a sky blue light emitting material layer. Alternatively, the first light emitting layer 144 may be composed of a combination (BR) of a blue light emitting material layer and a red light emitting material layer, a combination (BYG) of a blue light emitting material layer and a yellow-green (YG) light emitting material layer, or a combination (BG) of a blue light emitting material layer and a green light emitting material layer.
In one example, the second light emitting layer 154 may exhibit red (R), green (G), blue (B), or yellow-green (YG). In one exemplary embodiment, the first light emitting layer 144 may exhibit blue color, and the second light emitting layer 154 may exhibit green (G), yellow-green (YG), yellow (Y), or orange (O) color having a longer wavelength than blue color.
In one example, when the first light emitting layer 144 emits blue light, the first light emitting layer 144 may include at least one fluorescent host material selected from anthracene and its derivatives, pyrene and its derivatives, and a compound represented by chemical formula 1; and a fluorescent dopant doped into the host material.
In one example, the blue light emitting host material for the first light emitting layer 144 may include at least one selected from the group consisting of: 4,4 '-bis (2, 2' -diphenylvinyl) -1,1 '-biphenyl (DPVBi), 9, 10-bis- (2-naphthyl) Anthracene (ADN), 2,5,8,11- (tetra-tert-butylperylene) (TBADN), 2-tert-butyl-9, 10-bis (2-naphthyl) anthracene, 2-methyl-9, 10-bis (2-naphthyl) anthracene (MADN), and/or 2,2' - (1, 3, 5-benzenetriyl) -tris (1-phenyl-1-H-benzimidazole) (TBPi).
Details of the compound represented by chemical formula 1 are as described above.
Further, the blue dopant material for the first light emitting layer 144 may include at least one selected from the group consisting of: 4,4 '-bis (9-ethyl-3-carbazolylethylene) -1,1' -biphenyl (BCzVBi) and/or diphenyl- [4- (2- [1,1;4,1] terphenyl-4-yl-vinyl) -phenyl ] -amine (BD-1), spiro-DPVBi, spiro-CBP, distyrylbenzene (DSB) and derivatives thereof, distyrylarylene (DSA) and derivatives thereof, polyfluorene (PF) based Polymers and Polyphenylenevinylene (PPV) based polymers. Alternatively, the blue dopant may include a phosphorescent dopant as the iridium-based dopant. In this regard, the first light emitting layer 144 may include a sky blue light emitting material layer or a deep blue light emitting material layer. In this regard, the emission wavelength from the first emissive sub-stack (144) may be in the range of 440nm to 480 nm.
In one example, when the first light emitting layer 144 is implemented as a green (G) light emitting material layer, the first light emitting layer 144 may include a phosphorescent light emitting material layer including a host (e.g., CBP) and an iridium-based dopant (e.g., dp2Ir (acac), op2Ir (acac)), or may include a compound represented by chemical formula 1 as described above. However, the present disclosure is not limited thereto. Alternatively, the first light emitting layer 144 may include a fluorescent light emitting material layer including tris (8-hydroxyquinoline) aluminum (Alq). In this regard, the emission wavelength from the first emission layer 144 may be in the range of 510nm to 570 nm.
Further, when the first light emitting layer 144 is implemented as a red (R) light emitting material layer, the first light emitting layer 144 may include a phosphorescent light emitting material layer including a host material (e.g., CBP, a compound represented by chemical formula 1 as described above) and at least one dopant selected from bis (1-phenylisoquinoline) iridium acetylacetonate (PIQIr (acac)), bis ((1-phenylquinoline) iridium acetylacetonate (PQIr (acac)) and platinum octaethylporphyrin (PtOEP).
Alternatively, the first light emitting layer 144 may include a material including 1,3,4-
The fluorescent luminescent material layer of the diazole, tris (dibenzoylmethane) mono (1, 10-phenanthroline) europium (III) (PBD: eu (DBM) 3 (Phen)), or perylene and derivatives thereof. In this regard, the emission wavelength from the first emission layer 144 may be in the range of 600nm to 650 nm.
Alternatively, when the first light emitting layer 144 is implemented as a yellow (Y) light emitting material layer, the first light emitting layer 144 may be composed of a single yellow-green (YG) light emitting material layer, or a double layer of the YG light emitting material layer and the green (G) light emitting material layer. In one example, when the first light emitting layer 144 is implemented as a single yellow light emitting material layer, the yellow light emitting material layer may include a host material selected from CBP, bis (2-methyl-8-quinoline) -4- (phenylphenol) aluminum (BAlq), a compound represented by chemical formula 1 as described above; and a yellow-green phosphorescent dopant that emits yellow-green light. In this regard, the emission wavelength from the first emission layer 144 may be in the range of 510nm to 590 nm.
In an alternative embodiment, in order to improve the red light emitting efficiency of the light emitting diode 100 having the tandem structure, the first light emitting layer 144 may be implemented as a combination of two light emitting material layers, for example, a combination of a yellow-green light emitting material layer and a red light emitting material layer, or a combination of a blue light emitting material layer and a red light emitting material layer.
In one example, when the second light emitting layer 154 is implemented as a yellow-green light emitting material layer, the second light emitting layer 154 may be composed of a single yellow-green (YG) light emitting material layer, or a combination of a yellow-green light emitting material layer and a green (G) light emitting material layer. When the light emitting layer 154 is composed of a single layer structure of a yellow-green light emitting material layer, the second light emitting layer 154 may include a host material selected from CBP, BAlq, a compound represented by chemical formula 1 as described above; and a yellow-green phosphorescent dopant that emits a yellow-green color. However, the present disclosure is not limited thereto.
Alternatively, when the second light emitting layer 154 is implemented as a yellow light emitting material layer, the second light emitting layer 154 may include a host material selected from CBP, BAlq, a compound represented by chemical formula 1 as described above; and a phosphorescent dopant that emits yellow. However, the present disclosure is not limited thereto.
In one embodiment according to the present disclosure, at least one of the first light emitting layer and the second light emitting layer may include a host material including the compound of chemical formula 1 as described above.
In one example, the first electron transport layer 146 and the second electron transport layer 156 facilitate electron transport in the first light emitting sub-stack 140 and the second light emitting sub-stack 150, respectively. The first electron transport layer 146 and the second electron transport layer 156 may each comprise one selected from the group consisting of:
diazole, triazole, phenanthroline and benzo +.>
Oxazole, benzothiazole, benzimidazole, triazine and derivatives thereof.
In one example, the first electron transport layer 146 and the second electron transport layer 156 may each comprise at least one selected from the group consisting of: alq3, 2-Biphenyl-4-yl-5- (4-tert-butylphenyl) -1,3, 4-)
Diazole (PBD), spiro-PBD, lithium quinolinate (Liq), 2- [4- (9, 10-di-2-naphthyl-2-anthryl) phenyl ]-1-phenyl-1H benzimidazole, 3- (biphenyl-4-yl) -5- (4-tert-butylphenyl) -4-phenyl-4H-1, 2, 4-Triazole (TAZ), 4, 7-diphenyl-1, 10-phenanthroline (Bphen), tris (phenylquinoxaline) (TPQ), 1,3, 5-tris [ (3-pyridinyl) -benzene-3-yl]Benzene (TmPyPB) and/or 1,3, 5-tris (N-phenylbenzimidazol-2-yl) benzene (TPBI).
Alternatively, each of the first electron transport layer 146 and the second electron transport layer 156 may include the compound represented by chemical formula 1 as described above.
Alternatively, each of the first electron transport layer 146 and the second electron transport layer 156 may be doped with an alkali metal or alkaline earth metal compound. The metal component that may be used as a dopant for each of the first electron transport layer 146 and the second electron transport layer 156 may include alkali metals such as lithium (Li), sodium (Na), potassium (K), and cesium (Cs); and/or alkaline earth metals such as magnesium (Mg), strontium (Sr), barium (Ba), and radium (Ra). However, the present disclosure is not limited thereto. The alkali metal or alkaline earth metal compound may be added in a ratio of about 1 to 20% by weight. The present disclosure is not limited thereto.
The thickness of each of the first electron transport layer 146 and the second electron transport layer 156 may be 1nm to 150nm. When the thickness of each of the first electron transport layer 146 and the second electron transport layer 156 is 1nm or more, this can prevent the electron transport characteristics from being lowered. When the thickness of each of the first electron transport layer 146 and the second electron transport layer 156 is 150nm or less, this can prevent an increase in driving voltage due to an increase in the thickness of each of the first electron transport layer 146 and the second electron transport layer 156. The first electron transport layer 146 and the second electron transport layer 156 may be the same material or different materials.
The electron injection layer 158 is used to facilitate injection of electrons. The electron injection layer 158 may comprise an alkali halide-based material, such as LiF, naF, KF, rbF, csF, frF, beF 2 、MgF 2 、CaF 2 、SrF 2 、BaF 2 And RaF 2 The method comprises the steps of carrying out a first treatment on the surface of the And/or organic materials such as Liq (lithium quinolinate), lithium benzoate, sodium stearate, alq3, BAlq, PBD, spiro-PBD, and TAZ. Alternatively, the electron injection layer 158 may include the compound represented by chemical formula 1 as described above.
The thickness of the electron injection layer 158 may be in the range of 0.5nm to 50 nm. When the thickness of the electron injection layer 158 is 0.5nm or more, this can prevent the electron injection characteristics from being lowered. When the thickness of the electron injection layer 158 is 50nm or less, this can prevent the driving voltage from increasing due to an increase in the thickness of the electron injection layer 158.
According to an exemplary embodiment of the present disclosure, in the organic electroluminescent device 100 having a serial structure, a Charge Generation Layer (CGL) 160 for increasing current efficiency in each light emitting layer and smoothly distributing charges may be disposed between the first and second light emitting sub-stacks 140 and 150. That is, the charge generation layer 160 is located between the first and second light emitting sub-stacks 140 and 150, and the first and second light emitting sub-stacks 140 and 150 are connected to each other via the charge generation layer 160. The charge generation layer 160 may be implemented as a PN junction charge generation layer consisting of a vertical stack of an N-type charge generation layer 162 and a P-type charge generation layer 164.
The N-type charge generating layer 162 is located between the first electron transport layer 146 and the second hole transport layer 152. The P-type charge generation layer 164 is located between the N-type charge generation layer 162 and the second hole transport layer 152. The charge generation layer 160 generates charges and separates the charges into holes and electrons to provide electrons and holes to the first and second light emitting sub-stacks 140 and 150, respectively.
That is, the N-type charge generation layer 162 supplies electrons to the first electron transport layer 146 of the first light emitting sub-stack 140. Then, the first electron transport layer 146 supplies electrons to the first light emitting layer 144 adjacent to the first electrode 110. Meanwhile, the P-type charge generation layer 164 supplies holes to the second hole transport layer 152 of the second light emitting sub-stack 150. Then, the second hole transport layer 152 supplies holes to the second light emitting layer 154 adjacent to the second electrode 120.
In this regard, the P-type charge generation layer 164 may be made of an organic host material or metal doped with a P-type dopant. In this regard, the metal may include one selected from the group consisting of: al, cu, fe, pb, zn, au, pt, W, in, mo, ni and Ti, and alloys of at least two thereof. In addition, the P-type dopant and host materials may be materials known to those skilled in the art. In one example, the P-type dopant may include one selected from the group consisting of: F4-TCNQ, iodine and FeCl 3 、FeF 3 And SbCl 5 . Further, the host material may include at least one selected from the group consisting of: NPB, TPD, N, N, N ', N' -tetranaphthyl-benzidine (TNB) and HAT-CN.
Alternatively, the N-type charge generation layer 162 may include a metal compound (e.g., an alkali metal compound or an alkaline earth metal compound) as a dopant. The alkali metal or alkaline earth metal may be added in a proportion of about 1 to 30% by weight based on the weight of the organic compound according to the present disclosure. However, the present disclosure is not limited thereto.
The N-type charge generating layer 162 may be doped with an alkali metal compound or an alkaline earth metal compound to improve the ability of electrons to be injected into the first electron transport layer 146. Specifically, when an alkali metal or an alkaline earth metal is used as a dopant for the N-type charge generation layer 162, the alkali metal or the alkaline earth metal used as the dopant is bonded with the organic compound according to the present disclosure to form a band gap state (gap state). Accordingly, the difference in energy levels between the N-type charge generation layer 162 and the P-type charge generation layer 164 is reduced, and thus, the electron injection capability from the N-type charge generation layer 162 to the first electron transport 146 is improved.
In fig. 2, the organic electroluminescent device 200 includes a first electrode 210 and a second electrode 220 facing away from each other, and an organic light emitting layer 230 between the first electrode 210 and the second electrode 220. The organic light emitting layer 230 may include a vertical stack of a first light emitting sub-stack (ST 1) 240, a second light emitting sub-stack (ST 2) 250, a third light emitting sub-stack (ST 3) 270, a first charge generating layer (CGL 1) 260, and a second charge generating layer (CGL 2) 280. Alternatively, at least four light emitting sub-stacks and at least three charge generating layers may be disposed between the first electrode 210 and the second electrode 220.
As described above, the first electrode 210 may be used as an anode for injecting holes, and may be made of any conductive material having a high work function (e.g., ITO, IZO, or ZnO). The second electrode 220 may serve as a cathode for injecting electrons, and may be made of any conductive material having a low work function, for example, aluminum (Al), magnesium (Mg), or aluminum-magnesium alloy (AlMg).
The first and second charge generation layers 260 and 280 are located between the first and second light emitting sub-stacks 240 and 250 and between the second and third light emitting sub-stacks 250 and 270, respectively. A first light emitting sub-stack 240, a first charge generating layer 260, a second light emitting sub-stack 250, a second charge generating layer 280, and a third light emitting sub-stack 270 are sequentially stacked on the first electrode 210. That is, the first light emitting sub-stack 240 is located between the first electrode 210 and the first charge generating layer 260. The second light emitting sub-stack 250 is located between the first charge generating layer 260 and the second charge generating layer 280. The third light emitting sub-stack 270 is located between the second electrode 220 and the second charge generating layer 280.
The first light emitting sub-stack 240 may include a vertical stack of a hole injection layer 241, a first hole transport layer 242, a first light emitting layer 244, and a first electron transport layer 246 on the first electrode 210. In this regard, the hole injection layer 241 and the first hole transport layer 242 are located between the first electrode 210 and the first light emitting layer 244. The hole injection layer 241 is located between the first electrode 210 and the first hole transport layer 242. In addition, the first electron transport layer 246 is located between the first light emitting layer 244 and the first charge generating layer 260.
The hole injection layer 241, the first hole transport layer 242, the first light emitting layer 244, and the first electron transport layer 246 may be identical to the hole injection layer 141, the first hole transport layer 142, the first light emitting layer 144, and the first electron transport layer 146, respectively. Therefore, a description thereof will be omitted. For example, the first light emitting layer 244 may be implemented as a blue (B) light emitting material layer. In this regard, the emission wavelength from the first emission sub-stack 240 may be in the range of 440nm to 480 nm.
The second light emitting sub-stack 250 may include a vertical stack of a second hole transport layer 252, a second light emitting layer 254, and a second electron transport layer 256. The second hole transport layer 252 is located between the first charge generation layer 260 and the second light emitting layer 254. The second electron transport layer 256 is located between the second light emitting layer 254 and the second charge generating layer 280.
The second hole transport layer 252, the second light emitting layer 254, and the second electron transport layer 256 may be identical to the second hole transport layer 152, the second light emitting layer 154, and the second electron transport layer 156, respectively. Therefore, a description thereof will be omitted. For example, the second light emitting layer 254 may be implemented as a yellow-green (YG) light emitting material layer or a yellow (Y) light emitting material layer. In this regard, the emission wavelength from the second light emitting sub-stack 250 may be in the range of 510nm to 590nm or in the range of 460nm to 510 nm.
The third light emitting sub-stack 270 may include a vertical stack of a third hole transport layer 272, a third light emitting layer 274, a third electron transport layer 276, and an electron injection layer 278. The third hole transport layer 272 is located between the second charge generation layer 280 and the third light emitting layer 274. The third electron transport layer 276 is located between the third light emitting layer 274 and the second electrode 220. An electron injection layer 278 is located between the third electron transport layer 276 and the second electrode 220.
The third hole transport layer 272, the third electron transport layer 276, and the electron injection layer 278 may be identical to the second hole transport layer 152, the second electron transport layer 156, and the electron injection layer 158, respectively. Therefore, a description thereof will be omitted. The third light emitting layer 274 may be identical to the first light emitting layer 144 or the second light emitting layer 154. For example, the third light emitting layer 274 may be implemented as a blue (B) light emitting material layer. In this regard, the emission wavelength from the third light emitting sub-stack 270 may be in the range of 440nm to 480 nm. In another alternative embodiment, the third light emitting layer 274 may be implemented as a yellow-green (YG) light emitting material layer or a yellow (Y) light emitting material layer. In this case, the emission wavelength from the third light emitting sub-stack 270 may be in the range of 460nm to 590 nm.
In one embodiment according to the present disclosure, at least one of the first, second, and third light emitting layers includes the compound of chemical formula 1 as described above as a host material.
The first charge generation layer 260 is located between the first light emitting sub-stack 240 and the second light emitting sub-stack 250. The second charge generation layer 280 is located between the second light emitting sub-stack 250 and the third light emitting sub-stack 270. Each of the first and second charge generation layers 260 and 280 may be implemented as a PN junction charge generation layer composed of a vertical stack of each of the N-type charge generation layers 262 and 282 and each of the P-type charge generation layers 264 and 284.
In the first charge generation layer 260, an N-type charge generation layer 262 is located between the first electron transport layer 246 and the second hole transport layer 252. The P-type charge generation layer 264 is located between the N-type charge generation layer 262 and the second hole transport layer 252.
In addition, in the second charge generation layer 280, the N-type charge generation layer 282 is located between the second electron transport layer 256 and the third hole transport layer 272. The P-type charge generation layer 284 is located between the N-type charge generation layer 282 and the third hole transport layer 272.
Each of the first and second charge generation layers 260 and 280 generates and/or separates charges into electrons and holes to supply electrons and holes to each of the first, second, and third light emitting sub-stacks 240, 250, and 270.
That is, in the first charge generation layer 260, the N-type charge generation layer 262 supplies electrons to the first electron transport layer 246 of the first light emitting sub-stack 240. The P-type charge generation layer 264 supplies holes to the second hole transport layer 252 of the second light emitting sub-stack 250.
In the second charge generation layer 280, the N-type charge generation layer 282 supplies electrons to the second electron transport layer 256 of the second light emitting sub-stack 250. The P-type charge generation layer 284 supplies holes to the third hole transport layer 272 of the third light emitting sub-stack 270.
In this regard, each of the P-type charge generation layers 264 and 284 may be made of an organic host material or metal doped with a P-type dopant. In this regard, the metal may include one or more selected from the group consisting of: al, cu, fe, pb, zn, au, pt, W, in, mo, ni, ti, and alloys of at least two thereof. In addition, the P-type dopant and host materials may include materials conventionally employed by those skilled in the art. For example, the P-type dopant may include a material selected from the group consisting of: F4-TCNQ, iodine and FeCl 3 、FeF 3 And SbCl 5 . Further, the host material may include at least one material selected from the group consisting of: NPB, TPD, TNB and HAT-CN.
Alternatively, the N-type charge generation layers 262, 282 may contain a metal compound (including an alkali metal or an alkaline earth metal) as a dopant.
For example, each of the N-type charge generation layers 262 and 282 may include at least one material selected from the following in addition to the organic compound according to the present disclosure: liQ, liF, naF, KF, rbF, csF, frF, beF 2 、MgF 2 、CaF 2 、SrF 2 、BaF 2 And RaF 2 . However, the present disclosure is not limited thereto.
N-type charge generation layers 262 and 282 may be doped with alkali or alkaline earth metal compounds to improve the ability of electrons to be injected into electron transport layers 246 and 256.
The organic electroluminescent device according to the present disclosure may be applied to an organic light emitting display device and a lighting device using the organic electroluminescent device. In one example, fig. 3 is a schematic cross-sectional view of an organic light emitting display device according to one exemplary embodiment of the present disclosure.
As shown in fig. 3, the organic light emitting display apparatus 300 may include a substrate 301, an organic electroluminescent device 400, and an encapsulation film 390 covering the organic electroluminescent device 400. On the substrate 301, a driving thin film transistor Td as a driving element and an organic electroluminescent device 400 connected to the driving thin film transistor Td are provided.
Although not shown, the following components may be provided on the substrate 301: a data line and a gate line defining a pixel region and crossing each other; a power line extending in parallel with the gate line or the data line and spaced apart from the gate line or the data line; a switching thin film transistor connected to the gate line and the data line; and a storage (capacitor) connected to one electrode of the switching thin film transistor and the power supply line.
The driving thin film transistor Td is connected to the switching thin film transistor. The driving thin film transistor Td includes a semiconductor layer 310, a gate electrode 330, a source electrode 352, and a drain electrode 354.
The semiconductor layer 310 is formed on the substrate 301 and made of oxide semiconductor or polysilicon. When the semiconductor layer 310 is made of an oxide semiconductor material, a shielding pattern (not shown) may not be formed under the semiconductor layer 310. The shielding pattern prevents light from entering the semiconductor layer 310, thereby preventing the semiconductor layer 301 from being degraded by light. Alternatively, the semiconductor layer 310 may be made of polysilicon. In this case, impurities may be doped in both edges of the semiconductor layer 310.
On the semiconductor layer 310, a gate insulating film 320 made of an insulating material may be formed on the entire surface of the substrate 301. The gate insulating film 320 may be made of an inorganic insulating material (e.g., silicon oxide or silicon nitride).
On the gate insulating film 320, a gate electrode 330 made of a conductive material (e.g., metal) is formed in a central region of the semiconductor layer 310. The gate electrode 330 is connected to the switching thin film transistor.
On the gate electrode 330, an interlayer insulating film 340 made of an insulating material is formed on the entire surface of the substrate 301. The interlayer insulating film 340 may be made of an inorganic insulating material (e.g., silicon oxide or silicon nitride) or an organic insulating material (e.g., benzocyclobutene or photo-acryl).
The interlayer insulating film 340 has contact holes 342 and 344 exposing two lateral portions of the semiconductor layer 310. The contact holes 342 and 344 are spaced apart from the gate electrode 330 and are disposed at both sides of the gate electrode 330, respectively.
On the interlayer insulating film 340, a source electrode 352 and a drain electrode 354 made of a conductive material (e.g., metal) are provided. The source electrode 352 and the drain electrode 354 are disposed near the gate electrode 330 and spaced apart from each other. The source electrode 352 and the drain electrode 354 contact both sides of the semiconductor layer 310 via the contact holes 342 and 344, respectively. The source electrode 352 is connected to a power line (not shown).
The semiconductor layer 310, the gate electrode 330, the source electrode 352, and the drain electrode 354 define a driving thin film transistor Td. The driving thin film transistor Td has a coplanar structure in which the gate electrode 330, the source electrode 352, and the drain electrode 354 are disposed on the semiconductor layer 310 in a coplanar manner.
Alternatively, the driving thin film transistor Td may have an inverted staggered structure in which the gate electrode is located below the semiconductor layer and the source and drain electrodes are located above the semiconductor layer. In this case, the semiconductor layer may be made of amorphous silicon. In one example, the switching thin film transistor (not shown) may have substantially the same structure as the driving thin film transistor Td.
In one example, the organic light emitting display apparatus 300 may include a color filter 360 that absorbs light generated from the organic electroluminescent device 400. For example, the color filter 360 may absorb red (R), green (G), blue (B) and white (W) light. In this case, the color filter patterns absorbing red, green, and blue light may be separately provided on a pixel basis. Each of these color filter patterns may overlap a corresponding organic light emitting layer 430 of the organic electroluminescent device 400 emitting light having a corresponding wavelength. The organic light emitting display device 300 may be made to exhibit a full color range using the color filter 360.
For example, when the organic light emitting display apparatus 300 is of a bottom emission type, the color filter 360 absorbing light may be positioned above the interlayer insulating film 340 in the region of the organic electroluminescent device 400. In an alternative embodiment, when the organic light emitting display apparatus 300 is of a top emission type, the color filter may be positioned on top of the organic electroluminescent device 400, that is, on top of the second electrode 420. In one example, the thickness of the color filter 360 may be 2 μm to 5 μm. In this regard, the organic electroluminescent device 400 may be implemented as an organic electroluminescent device having a series structure as shown in fig. 1 and 2.
In one example, a protective layer 370 having a drain contact hole 372 exposing the drain electrode 354 of the driving thin film transistor Td may be formed to cover the driving thin film transistor Td.
On the protective layer 370, a first electrode 410 connected to the drain electrode 354 of the driving thin film transistor Td via the drain contact hole 372 may be formed based on the pixel region.
The first electrode 410 may function as an anode, and may be made of a conductive material having a relatively high work function value. For example, the first electrode 410 may be made of a transparent conductive material such as ITO, IZO, or ZnO.
In one example, when the organic light emitting display device 300 is of a top emission type, a reflective electrode or a reflective layer may be further formed under the first electrode 410. For example, the reflective electrode or the reflective layer may be made of any one of aluminum (Al), silver (Ag), nickel (Ni), and aluminum-palladium-copper (APC alloy).
On the protective layer 370, a bank layer 380 is formed to cover an edge of the first electrode 410. The bank layer 380 exposes a central region of the first electrode 410 corresponding to the pixel region.
An organic light emitting layer 430 is formed on the first electrode 410. In one example, the organic light emitting layer 430 may have at least two light emitting sub-stacks shown in fig. 1 and 2. Accordingly, the organic electroluminescent device 400 may have a series structure.
A second electrode 420 is formed on the organic light emitting layer 430. The second electrode 420 may be disposed over the entire display area, and may be made of a conductive material having a relatively low work function value, and may serve as a cathode. For example, the second electrode 420 may be made of any one of aluminum (Al), magnesium (Mg), and aluminum-magnesium alloy (AlMg).
The first electrode 410, the organic light emitting layer 430, and the second electrode 420 together define the organic electroluminescent device 400.
On the second electrode 420, an encapsulation film 390 is formed to prevent external moisture from penetrating into the organic electroluminescent device 400. Although not shown, the encapsulation film 390 may have a three-layer structure in which a first inorganic layer and an organic layer and a second inorganic layer are sequentially stacked. However, the present invention is not limited thereto.
As used herein, the term "halogen group" may include fluorine, chlorine, bromine or iodine.
As used herein, the term "alkyl" means a monovalent substituent derived from a straight or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, and hexyl.
As used herein, the term "alkenyl" means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having one or more carbon-carbon double bonds and from 2 to 40 carbon atoms. Examples include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
As used herein, the term "alkynyl" means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having one or more carbon-carbon triple bonds and from 2 to 40 carbon atoms. Examples include, but are not limited to, ethynyl, 2-propynyl, and the like.
As used herein, the term "aryl" means a monovalent substituent derived from an aromatic hydrocarbon having a single ring or a combination of two or more rings and having 2 to 60 carbon atoms. Further, such aryl groups may have a form in which two or more rings are simply pendent from each other or are condensed with each other. Examples of such aryl groups include, but are not limited to, phenyl, naphthyl, phenanthryl, anthracyl, dimethylfluorenyl, and the like.
As used herein, the term "heteroaryl" means a monovalent substituent derived from a mono-or polyheterocyclic aromatic hydrocarbon having 6 to 30 carbon atoms. In this regard, at least one carbon, preferably 1 to 3 carbons in the ring is substituted with a heteroatom (e.g., N, O, S or Se). Furthermore, such heteroaryl groups may have a form in which two or more rings are simply pendent from each other or are fused to an aryl group. Examples of such heteroaryl groups include 6-membered monocyclic rings, such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and triazinyl; polycyclic rings, e.g. phenones 
Thienyl, indolizinyl, indolyl, purinyl, quinolinyl, benzothiazole, carbazolyl and 2-furyl, N-imidazolyl, 2-iso->
Oxazolyl, 2-pyridyl, 2-pyrimidinyl, and the like. However, the present disclosure is not limited thereto.
As used herein, the term "aryloxy" refers to a monovalent substituent represented by RO-wherein R represents an aryl group having 6 to 60 carbon atoms. Examples of such aryloxy groups include, but are not limited to, phenoxy, naphthoxy, diphenoxy, and the like.
As used herein, the term "alkyloxy" means a monovalent substituent represented by R 'O-, wherein R' means an alkyl group having 1 to 40 carbon atoms. Such alkyloxy groups have a linear, branched, or cyclic structure. Examples of alkoxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.
As used herein, the term "alkoxy" refers to a straight, branched, or cyclic chain. The carbon number of the alkoxy group is not particularly limited, but the alkoxy group preferably has 1 to 20 carbon atoms. Specific examples thereof include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzoxy.
As used herein, the term "aralkyl" means a monovalent group derived from an alkyl group by substitution of one or more hydrogen atoms with an aryl group. Preferred aralkyl groups include lower alkyl groups. Non-limiting examples of suitable aralkyl groups include benzyl, 2-phenethyl, and naphthylmethyl. Bonding to the parent moiety is accomplished via an alkyl group.
As used herein, the term "arylamino" means an amine substituted with an aryl group having 6 to 30 carbon atoms.
As used herein, the term "alkylamino" means an amine substituted with an alkyl group having 1 to 30 carbon atoms.
As used herein, the term "aralkylamino" means an amine substituted with an arylalkyl group having 6 to 30 carbon atoms.
As used herein, the term "heteroarylamino" means an amine substituted with a heterocyclyl and an aryl group having 6 to 30 carbon atoms.
As used herein, the term "heteroaralkyl" means an arylalkyl group substituted with a heterocyclyl group.
As used herein, the term "cycloalkyl" means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantine (amantine), and the like.
As used herein, the term "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 carbon atoms, wherein at least one carbon, preferably 1 to 3 carbons, in the ring is substituted with a heteroatom (e.g., N, O, S or Se). Examples of such heterocycloalkyl groups include, but are not limited to, morpholine, piperazine, and the like.
As used herein, the term "alkylsilyl" refers to silyl groups substituted with alkyl groups having 1 to 40 carbon atoms.
As used herein, the term "arylsilyl" means silyl substituted with aryl groups having 6 to 60 carbon atoms.
As used herein, the term "fused ring" means a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, a fused heteroaromatic ring, or a combination thereof.
As used herein, the term "a particular group bonds to an adjacent group to form a ring" means that the particular group bonds to an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a fused ring thereof.
As used herein, the term "aliphatic hydrocarbon ring" refers to a ring that is not aromatic and consists of only carbon and hydrogen atoms.
As used herein, examples of "aromatic hydrocarbon rings" include, but are not limited to, phenyl, naphthyl, anthracenyl, and the like.
As used herein, the term "aliphatic heterocyclic" means an aliphatic ring comprising one or more heteroatoms.
As used herein, the term "aromatic heterocycle" means an aromatic ring comprising one or more heteroatoms.
As used herein, aliphatic hydrocarbon rings, aromatic hydrocarbon rings, aliphatic heterocycles, and aromatic heterocycles may be monocyclic or polycyclic.
As used herein, the term "substituted" means that the hydrogen atom in the compound that is bonded to a carbon atom becomes another substituent. The position where substitution occurs may refer to the position where a hydrogen atom is substituted. That is, the position is not limited to a specific position as long as the substituent can be substituted at the position. When two or more substitutions occur, the two or more substituents may be the same or different.
As used herein, the term "unsubstituted" means that a hydrogen atom replaces another substituent. As used herein, a hydrogen atom may include hydrogen, deuterium, and tritium.
According to the present disclosure, an organic electroluminescent device has an organic layer including a deuterated anthracene organic compound to achieve reduced driving voltage, increased lifetime, and excellent light emitting efficiency and External Quantum Efficiency (EQE) characteristics.
Drawings
Fig. 1 shows a schematic cross-sectional view of an organic electroluminescent device having a tandem structure having two light emitting sub-stacks and including a compound represented by chemical formula 1 according to an embodiment of the present disclosure.
Fig. 2 shows a schematic cross-sectional view of an organic electroluminescent device having a tandem structure having three light emitting sub-stacks and including a compound represented by chemical formula 1 according to another embodiment of the present disclosure.
Fig. 3 is a sectional view schematically showing an organic light emitting display apparatus having an organic electroluminescent device according to still another embodiment of the present disclosure.
Detailed Description
Embodiments of the present disclosure are provided to more fully describe the present disclosure to those skilled in the art. The following embodiments may be modified in various different forms. The scope of the present disclosure is not limited to the following embodiments. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of the disclosure to those skilled in the art.
According to a preferred embodiment of the present disclosure, the compound represented by chemical formula 1 may be selected from the following compounds, but is not limited thereto:
hereinafter, a method for synthesizing the compounds represented by chemical formula 1 and chemical formula 2 will be described as a representative example.
However, the method for synthesizing a compound according to the present disclosure is not limited to the methods exemplified below. The compounds according to the present disclosure may be prepared by the methods illustrated below and known in the art.
Synthesis example 1: synthesis of Compound 6
4- (10-Bromoanthracene-9-yl) dibenzofuran-d 8 (5.54 g,10.0 mmol), (4- (naphthalen-1-yl) phenyl) boronic acid (2.73 g,11.0 mmol), potassium carbonate (5.16 g,20 mmol), 100mL toluene, 20mL water and 100mL ethanol were mixed with each other.
Then, tetrakis (triphenylphosphine) palladium (0.231 g,0.20 mmol) was added to the mixture, followed by reflux for 10 hours. Thereafter, the resultant mixture was cooled to room temperature, and then water was added thereto. Layer separation was performed to obtain an organic layer. With MgSO 4 The organic layer is treated to remove moisture therefrom.
After the organic layer was filtered, the filtrate was concentrated under reduced pressure. The concentrate was subjected to column chromatography using methylene chloride and n-hexane as developing agents to obtain 3.38g (yield: 25%) of the present compound 6.
MS(MALDI-TOF)m/z：554[M] +
< synthetic example 2: synthesis of Compound 7
4- (10-Bromoanthracene-9-yl) dibenzofuran-d 8 (5.54 g,10.0 mmol), (3- (naphthalen-1-yl) phenyl) boronic acid (2.73 g,11.0 mmol), potassium carbonate (5.16 g,20 mmol), 100mL toluene, 20mL water and 100mL ethanol were mixed with each other.
Then, tetrakis (triphenylphosphine) palladium (0.231 g,0.20 mmol) was added to the mixture, followed by reflux for 10 hours. Thereafter, the resultant mixture was cooled to room temperature, and then water was added thereto. Layer separation was performed to obtain an organic layer. With MgSO 4 The organic layer is treated to remove moisture therefrom.
After the organic layer was filtered, the filtrate was concentrated under reduced pressure. The concentrate was subjected to column chromatography using methylene chloride and n-hexane as developing agents to obtain 3.38g (yield: 61%) of the present compound 7.
MS(MALDI-TOF)m/z：554[M] +
< synthesis example 3: synthesis of Compound 1
3.92g (10.0 mmol) of starting material 1-A, 2.33g (11 mmol) of starting material 1-B, potassium carbonate (5.16 g,20 mmol), 100mL of toluene, 20mL of water and 100mL of ethanol were mixed with each other.
Then, tetrakis (triphenylphosphine) palladium (0.231 g,0.20 mmol) was added to the mixture, followed by reflux for 10 hours. Thereafter, the resulting mixture was cooled to room temperature, and then water was added thereto. Layer separation was performed to obtain an organic layer. With MgSO 4 The organic layer is treated to remove moisture therefrom.
After the organic layer was filtered, the filtrate was concentrated under reduced pressure. The concentrate was subjected to column chromatography using methylene chloride and n-hexane as developing agents to obtain 1g (yield: 62%) of the present compound 1.
MS(MALDI-TOF)m/z：478[M] +
< synthetic example 4: synthesis of Compound 3
2.7g (yield: 51%) of the present compound 3 was obtained in the same manner as in Synthesis example 1 except that 2.44g (11 mmol) of the starting material 3-B was used instead of (4- (naphthalen-l-yl) phenyl) boronic acid.
MS(MALDI-TOF)m/z：528[M] +
< synthetic example 5: synthesis of Compound 5-
3.66g (yield 66%) of the present compound 5 was obtained in the same manner as in synthesis example 1 except that 2.73g (11 mmol) of the starting material 5-B was used instead of (4- (naphthalen-l-yl) phenyl) boronic acid.
MS(MALDI-TOF)m/z：554[M] +
< synthetic example 6: synthesis of Compound 9-
3.5g (yield 63%) of the present compound 9 was obtained in the same manner as in synthesis example 1 except that 2.44g (11 mmol) of the starting material 9-B was used instead of (4- (naphthalen-l-yl) phenyl) boronic acid.
< synthetic example 7: synthesis of Compound 10
3.5g (yield 63%) of the present compound 10 was obtained in the same manner as in Synthesis example 1 except that 2.73g (11 mmol) of the starting material 10-B was used instead of (4- (naphthalen-l-yl) phenyl) boronic acid.
< synthesis example 8: synthesis of Compound 13
3.32g (yield 60%) of the present compound 13 was obtained in the same manner as in Synthesis example 3 except that 3.17g (11 mmol) of the starting material 13-B was used instead of the starting material 1-B.
MS(MALDI-TOF)m/z：554[M] +
< synthetic example 9: synthesis of Compound 14-
3.35g (yield: 64%) of the present compound 14 was obtained in the same manner as in Synthesis example 3 except that 3.92g (10 mmol) of the starting material 14-A and 3.17g (11 mmol) of the starting material 13-B were used in place of the starting materials 1-A and 1-B.
MS(MALDI-TOF)m/z：554[M] +
< synthetic example 10: synthesis of Compound 17
3.74g (yield 62%) of the present compound 17 was obtained in the same manner as in Synthesis example 3 except that 4.401g (10 mmol) of the starting material 17-A and 3.17g (11 mmol) of the starting material 13-B were used in place of the starting materials 1-A and 1-B.
MS(MALDI-TOF)m/z：604[M] +
< synthesis example 11: synthesis of Compound 21
2.86g (yield 58%) of the present compound 21 was obtained in the same manner as in Synthesis example 3 except that 3.98g (10 mmol) of the starting material 21-A and 2.4g (11 mmol) of the starting material 21-B were used in place of the starting materials 1-A and 1-B.
MS(MALDI-TOF)m/z：492[M] +
< synthetic example 12: synthesis of Compound 22
2.98g (yield 52%) of the present compound 22 was obtained in the same manner as in Synthesis example 3 except that 4.78g (10 mmol) of the starting material 22-A and 2.4g (11 mmol) of the starting material 21-B were used in place of the starting materials 1-A and 1-B.
MS(MALDI-TOF)m/z：572[M] +
< synthesis example 13: synthesis of Compound 36 ]
2.86g (yield 58%) of the present compound 36 was obtained in the same manner as in Synthesis example 3 except that 3.98g (10 mmol) of the starting material 36-A and 2.4g (11 mmol) of the starting material 36-B were used in place of the starting materials 1-A and 1-B.
MS(MALDI-TOF)m/z：492[M] +
< synthesis example 14: synthesis of Compound 39
2.98g (yield 52%) of the present compound 39 was obtained in the same manner as in Synthesis example 3 except that 4.78g (10 mmol) of the starting material 39-A and 2.4g (11 mmol) of the starting material 39-B were used in place of the starting materials 1-A and 1-B.
MS(MALDI-TOF)m/z：572[M] +
< synthesis example 15: synthesis of Compound 44
3.66g (yield 66%) of the present compound 44 was obtained in the same manner as in Synthesis example 3 except that 4.30g (10 mmol) of the starting material 44-A and 2.73g (11 mmol) of the starting material 5-B were used in place of the starting materials 1-A and 1-B.
MS(MALDI-TOF)m/z：554[M] +
< synthesis example 16: synthesis of Compound 72
3.06g (yield 58%) of the present compound 72 was obtained in the same manner as in Synthesis example 3 except that 3.91g (10 mmol) of the starting material 14-A and 2.88g (11 mmol) of the starting material 72-B were used in place of the starting materials 1-A and 1-B.
MS(MALDI-TOF)m/z：528[M] +
< synthetic example 17: synthesis of Compound 73 ]
2.77g (yield 58%) of the present compound 73 was obtained in the same manner as in Synthesis example 3 except that 3.41g (10 mmol) of the starting material 73-A and 2.88g (11 mmol) of the starting material 72-B were used in place of the starting materials 1-A and 1-B.
MS(MALDI-TOF)m/z：478[M] +
< synthetic example 18: synthesis of Compound 79
3.66g (yield 66%) of the present compound 79 was obtained in the same manner as in Synthesis example 3 except that 4.16g (10 mmol) of the starting material 79-A and 2.88g (11 mmol) of the starting material 79-B were used in place of the starting materials 1-A and 1-B.
MS(MALDI-TOF)m/z：554[M] +
< synthesis example 19: synthesis of Compound 108
2.83g (yield 52%) of the present compound 108 was obtained in the same manner as in Synthesis example 3, except that 3.45g (10 mmol) of the starting material 108-A and 3.55g (11 mmol) of the starting material 108-B were used in place of the starting materials 1-A and 1-B.
MS(MALDI-TOF)m/z：57[M] +
< synthetic example 20: synthesis of Compound 111
3.26g (yield 66%) of the present compound 111 was obtained in the same manner as in Synthesis example 3 except that 3.90g (10 mmol) of the starting material 1-A and 2.51g (11 mmol) of the starting material 111-B were used in place of the starting materials 1-A and 1-B.
MS(MALDI-TOF)m/z：494[M] +
< synthesis example 21: synthesis of Compound 113
3.76g (yield 66%) of the present compound 113 was obtained in the same manner as in Synthesis example 3 except that 4.46g (10 mmol) of the starting material 113-A and 2.73g (11 mmol) of the starting material 5-B were used in place of the starting materials 1-A and 1-B.
MS(MALDI-TOF)m/z：570[M] +
< synthesis example 22: synthesis of Compound 114
3.53g (yield 62%) of the present compound 114 was obtained in the same manner as in Synthesis example 2 except that 4.46g (10 mmol) of the starting material 113-A was used instead of 4- (10-bromoanthracene-9-yl) dibenzofuran-d 8.
MS(MALDI-TOF)m/z：570[M] +
< synthesis example 23: synthesis of Compound 199-
2.64g (yield 51%) of the present compound 199 was obtained in the same manner as in Synthesis example 1 except that 2.33g (11 mmol) of the starting material 1-B was used instead of (4- (naphthalen-l-yl) phenyl) boronic acid.
< synthesis example 24: synthesis of Compound 224
3.76g (yield 66%) of the present compound 224 was obtained in the same manner as in Synthesis example 3 except that 4.46g (10 mmol) of the starting material 113-A and 3.17g (11 mmol) of the starting material 13-B were used in place of the starting materials 1-A and 1-B.
MS(MALDI-TOF)m/z：570[M] +
< present example 1: manufacturing of organic electroluminescent device
An Ag alloy layer as a light reflection layer and an ITO (10 nm) layer as an anode of an organic electroluminescent device were sequentially deposited on a substrate. Then, patterning is performed using a photolithography process to divide the substrate region into a cathode region and an anode region and an insulating layer region. Performing UV ozone treatment and using O 2 :N 2 The surface of the plasma is treated to increase the work function of the anode and to perform a descumming (descum) process. Then, on the ITO layer
1,4,5,8,9,11-hexaazabenzophenanthrene-hexacyanonitrile (HAT-CN) is deposited as a Hole Injection Layer (HIL).
Then, N4, N4, N4', N4' -tetra ([ 1,1' -biphenyl) is vacuum deposited on the Hole Injection Layer (HIL) ]-4-yl) - [1,1' -biphenyl]-4,4' -diamine to form
Thick Hole Transport Layer (HTL). />
Then, on top of the Hole Transport Layer (HTL), N-phenyl-N- (4- (spiro [ benzo [ de ] anthracene-7, 9-fluorene ] -2-yl) phenyl) dibenzo [ b, d ] furan-4-amine was deposited as an Electron Blocking Layer (EBL) at a thickness of 150 angstroms. Then, on top of the Electron Blocking Layer (EBL), the present compound 6 as a host material of the light emitting layer (EML) is deposited. Meanwhile, N1, N6-tetrakis (4- (1-silyl) phenyl) pyrene-1, 6-diamine as a dopant is doped in a host material to form an emitting layer (EML).
Then, 2- (4- (9, 10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H-benzo [ d ] is deposited on the EML layer]Mixture of imidazole and LiQ (weight ratio 1:1) to
As an Electron Transport Layer (ETL). Then, with +.>
A mixture of magnesium (Mg) and silver (Ag) (ratio 9:1) was deposited as a cathode.
Next, N4 '-diphenyl-N4, N4' -bis (4- (9-phenyl-9H-carbazol-3-yl) phenyl- [1,1 '-biphenyl ] -4,4' -diamine was deposited on the cathode layer to a thickness of 63nm to 65nm as cap layer (CPL).
Then we adhered the sealing cap to the cap layer (CPL) with UV curable adhesive to protect the organic electroluminescent device from the atmosphere O 2 Or the effects of moisture. In this way, an organic electroluminescent device was manufactured.
< present examples 2 to 11: manufacturing of organic electroluminescent device
An organic electroluminescent device was manufactured in the same manner as in this example 1, except that the present compounds 1, 3, 5, 7,9, 10, 13, 14, 17, 21 and 22 of the following table 1 were used as host materials instead of the compound 6.
< present example 12: manufacturing of organic electroluminescent device
An Ag alloy layer as a light reflection layer and an ITO (10 nm) layer as an anode of an organic electroluminescent device were sequentially deposited on a substrate. Then, letPatterning is performed using a photolithography process to divide the substrate region into a cathode region and an anode region and an insulating layer region. Performing UV ozone treatment and using O 2 :N 2 The surface of the plasma is treated to increase the work function of the anode and to perform a descumming process. Then, on the ITO layer
1,4,5,8,9,11-hexaazabenzophenanthrene-hexanitrile (HAT-CN) is deposited as a Hole Injection Layer (HIL).
Then, N4, N4, N4', N4' -tetra ([ 1,1' -biphenyl) is vacuum deposited on the Hole Injection Layer (HIL)]-4-yl) - [1,1' -biphenyl]-4,4' -diamine to form
Thick Hole Transport Layer (HTL).
Then, on top of the Hole Transport Layer (HTL), N-phenyl-N- (4- (spiro [ benzo [ de ] anthracene-7, 9-fluorene ] -2-yl) phenyl) dibenzo [ b, d ] furan-4-amine was deposited as an Electron Blocking Layer (EBL) at a thickness of 150 angstroms. Then, on top of the Electron Blocking Layer (EBL), the present compound 36 is deposited as a host material for the light emitting layer (EML). Meanwhile, the following compound 1-B as a dopant was doped in a host material to form an emission layer (EML).
[ Compound 1-B ]
Then, 2- (4- (9, 10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H-benzo [ d ] is deposited on the EML layer]Mixture of imidazole and LiQ (weight ratio 1:1) to
As an Electron Transport Layer (ETL). Then, with +.>
Is deposited as a negative electrode with a mixture of magnesium (Mg) and silver (Ag) (ratio 9:1)And (5) a pole.
Next, N4 '-diphenyl-N4, N4' -bis (4- (9-phenyl-9H-carbazol-3-yl) phenyl- [1,1 '-biphenyl ] -4,4' -diamine was deposited on the cathode layer to a thickness of 63nm to 65nm as cap layer (CPL).
Then we adhered the sealing cap to the cap layer (CPL) with UV curable adhesive to protect the organic electroluminescent device from the atmosphere O 2 Or the effects of moisture. In this way, an organic electroluminescent device was manufactured.
< present examples 13 to 22: manufacturing of organic electroluminescent device
An organic electroluminescent device was manufactured in the same manner as in example 12, except that the present compounds 39, 44, 79, 72, 73, 108, 111, 113, 199, 224 of the following table 1 were used as host materials instead of the compound 36.
Comparative examples 1 to 7: manufacturing of organic electroluminescent device
A comparative organic electroluminescent device was manufactured using the same method as in this example 1, except that the following comparative compounds a to J were used as host materials instead of compound 6.
< experimental example 1: analysis of organic electroluminescent device characteristics
For the organic electroluminescent devices prepared according to the present examples 1 to 22 and comparative examples 1 to 9, analysis was performed at 10mA/cm 2 Driving voltage and luminous efficiency characteristics at current at the time of driving the device, and at 20mA/cm 2 Lifetime characteristics at device acceleration. The results are shown in table 1 below.
The "T95 lifetime" in table 1 below refers to the duration of time required for the display device to lose 5% of its initial brightness. T95 lifetime is the most difficult customer requirement to meet. Thus, the T95 lifetime determines whether an image burn occurs in the display device.
TABLE 1
As shown in table 1, this example 1, which employs the compound according to the present disclosure as a host material, exhibited excellent current efficiency and increased lifetime by up to about 47% as compared to comparative examples 1 to 3, which have similar compound structures therein. Further, it was found that the present embodiments 1 to 22 according to the present disclosure in which the polar molecules were bonded to anthracene have lower driving voltages than the comparative examples 7 to 8 in which the polar molecules were not bonded.
From these findings, it can be concluded that: the anthracene compounds according to the present disclosure achieve lower drive voltages than achieved with host materials that are not polar, and deuteration produces longer lifetimes.
Thus, it can be determined that the compound represented by chemical formula 1 of the present disclosure contains a polar molecule (e.g., dibenzofuran or dibenzothiophene), and that anthracene deuteration produces excellent characteristics (e.g., low driving voltage realization and long lifetime).
< present examples 23 to 24: manufacturing of organic electroluminescent device
An organic electroluminescent device was manufactured in the same manner as in this example 1, except that compound 7 or 114 of table 2 below was used as a host material instead of compound 6.
< experimental example 2: analysis of organic electroluminescent device characteristics
For the organic electroluminescent devices prepared according to the present examples 23 to 24 and comparative examples 4 to 8 and 10, analysis was performed at 10mA/cm 2 Driving voltage and luminous efficiency characteristics at the time of driving the device at a current of 20mA/cm 2 Lifetime characteristics at device acceleration. The results are shown in table 2 below.
The "T95 lifetime" in table 2 below refers to the duration of time required for the display device to lose 5% of its initial brightness. T95 lifetime is the most difficult customer requirement to meet. Thus, the T95 lifetime determines whether an image burn occurs in the display device.
TABLE 2
As shown in table 2, this example 23, which employed the compound according to the present disclosure as a host material, exhibited excellent current efficiency and increased lifetime by up to about 78% as compared to comparative examples 4 to 6, which had similar compound structures therein.
As shown in table 2, this example 24, which employed the compound according to the present disclosure as a host material, exhibited excellent current efficiency and increased lifetime by up to about 23% as compared to comparative example 10, which had a similar compound structure therein.
Further, it was found that the present embodiments 24 and 23 according to the present disclosure in which the polar molecules were bonded to anthracene have lower driving voltages than the comparative examples 7 to 8 in which the polar molecules were not bonded.
Thus, it can be determined that the compound represented by chemical formula 1 of the present disclosure contains a polar molecule (e.g., dibenzofuran or dibenzothiophene), and that anthracene deuteration produces excellent characteristics (e.g., low driving voltage realization and long lifetime).
The description of the disclosed implementations is provided to enable any person skilled in the art to make or use the disclosure. Various modifications to these embodiments will be readily apparent to those skilled in the art of the present disclosure. The general principles defined herein may be applied to other embodiments without departing from the scope of the disclosure. Thus, the present disclosure should not be construed as limited to the embodiments set forth herein but is to be accorded the widest scope consistent with the principles and novel features set forth herein.
Claims (7)
1. A compound selected from the group consisting of:
2. an organic electroluminescent device comprising:
a first electrode;
a second electrode opposite to the first electrode; and
at least one organic layer between the first electrode and the second electrode, wherein the at least one organic layer comprises at least one compound according to claim 1.
3. The organic electroluminescent device of claim 2, wherein the organic layer defines one selected from the group consisting of: a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
4. The organic electroluminescent device according to claim 2, wherein the organic layer defines a light emitting layer, wherein the light emitting layer comprises the compound according to claim 1 as a host material.
5. An organic electroluminescent device comprising:
a first emissive sub-stack for rendering a first color light; and
a second light emitting sub-stack stacked on the first light emitting sub-stack, wherein the second light emitting sub-stack exhibits a second color light,
wherein at least one of the first light emitting sub-stack and the second light emitting sub-stack comprises a host material,
Wherein the host material comprises a compound selected from the group consisting of:
6. the organic electroluminescent device according to claim 5, wherein the first light-emitting sub-stack comprises a first light-emitting layer,
wherein the second light emitting sub-stack comprises a second light emitting layer,
wherein at least one of the first light emitting layer and the second light emitting layer comprises the host material.
7. The organic electroluminescent device according to claim 5, wherein the first light-emitting sub-stack comprises a vertical stack of a first electrode, a first hole transport layer, a first light-emitting layer and a first electron transport layer in this order,
wherein the second light emitting sub-stack comprises a vertical stack of a second hole transporting layer, a second light emitting layer and a second electron transporting layer in this order,
wherein at least one of the first light emitting layer and the second light emitting layer comprises the host material.
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| KR1020180099515A KR102136806B1 (en) | 2018-03-28 | 2018-08-24 | Novel organic compounds and an organic electroluminescent device comprising the same |
| KR10-2018-0099515 | 2018-08-24 |
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| CN112789270A (en) * | 2018-10-09 | 2021-05-11 | 出光兴产株式会社 | Novel compound, organic electroluminescent element, and electronic device |
| WO2020080714A1 (en) | 2018-10-16 | 2020-04-23 | 주식회사 엘지화학 | Organic compound and organic light-emitting device comprising same |
| CN110642724A (en) * | 2019-10-15 | 2020-01-03 | 吉林奥来德光电材料股份有限公司 | Blue light electroluminescent material and application thereof |
| US20220165966A1 (en) * | 2019-10-30 | 2022-05-26 | Lg Chem, Ltd. | Anthracene compound and organic light-emitting device comprising same |
| KR20210085531A (en) * | 2019-12-30 | 2021-07-08 | 엘지디스플레이 주식회사 | Organic light emitting diode and orgnic light emitting device including the same |
| US20220238817A1 (en) * | 2020-01-21 | 2022-07-28 | Lg Chem, Ltd. | Compound and organic light-emitting device comprising same |
| CN113892196A (en) * | 2020-01-23 | 2022-01-04 | 株式会社Lg化学 | Organic light emitting device |
| CN117209460A (en) * | 2023-11-09 | 2023-12-12 | 浙江华显光电科技有限公司 | Organic photoelectric compound, composition with same and organic light-emitting device |
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